#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:01:40 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304783 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064313.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7064313 loop_ _publ_author_name 'Sathish, Kota' 'Majhi, Subir' 'Parida, Ankita' 'Nagaraju, Sakkani' 'Kashinath, Dhurke' _publ_section_title ; Solvent directed base-enabled diastereodivergent domino cycloaddition of isoxazole--oxindole styrenes and Michael additions of isoxazole--styrenes with vinyl malononitriles ; _journal_issue 5 _journal_name_full 'New Journal of Chemistry' _journal_page_first 2350 _journal_page_last 2355 _journal_paper_doi 10.1039/D5NJ03725E _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C25 H23 N5 O4' _chemical_formula_sum 'C25 H23 N5 O4' _chemical_formula_weight 457.48 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2022-10-17 _audit_creation_method ; Olex2 1.3-ac4 (compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1) ; _audit_update_record ; 2025-09-08 deposited with the CCDC. 2025-12-15 downloaded from the CCDC. ; _cell_angle_alpha 80.600(2) _cell_angle_beta 89.223(2) _cell_angle_gamma 77.075(2) _cell_formula_units_Z 4 _cell_length_a 11.5473(3) _cell_length_b 13.9900(4) _cell_length_c 14.7675(3) _cell_measurement_reflns_used 14666 _cell_measurement_temperature 304.9 _cell_measurement_theta_max 26.1320 _cell_measurement_theta_min 2.0750 _cell_volume 2293.32(10) _computing_cell_refinement 'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment air _diffrn_ambient_temperature 304.9 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix3000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.958 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 12.00 54.00 0.50 5.36 -- -14.97 0.00 30.00 84 2 \w 60.00 86.00 0.50 5.36 -- 16.22 45.00 90.00 52 3 \w -5.00 52.00 0.50 5.36 -- 16.22 45.00 0.00 114 4 \w 48.00 87.00 0.50 5.36 -- 16.22 30.00 -30.00 78 5 \w -7.00 41.00 0.50 5.36 -- 16.22 30.00 -30.00 96 6 \w -14.00 22.00 0.50 5.36 -- -14.97 -94.00 -60.00 72 7 \w -26.00 8.00 0.50 5.36 -- -14.97 -94.00 -90.00 68 8 \w 22.00 47.00 0.50 5.36 -- 16.22-135.00-125.00 50 9 \w -36.00 10.00 0.50 5.36 -- -14.97 -94.00-150.00 92 10 \w -85.00 8.00 0.50 5.36 -- -14.97 -61.00-150.00 186 11 \w -39.00 55.00 0.50 5.36 -- -14.97 45.00-180.00 188 12 \w 40.00 86.00 0.50 5.36 -- 16.22 45.00-150.00 92 13 \w -8.00 27.00 0.50 5.36 -- 16.22 45.00-150.00 70 14 \w -66.00 -22.00 0.50 5.36 -- -14.97 125.00-120.00 88 15 \w -71.00 -16.00 0.50 5.36 -- -14.97 135.00 -59.00 110 16 \w -31.00 -5.00 0.50 5.36 -- -14.97 -77.00 60.00 52 17 \w -30.00 16.00 0.50 5.36 -- -14.97 -94.00 30.00 92 18 \w 20.00 47.00 0.50 5.36 -- 16.22-134.00 53.00 54 19 \w -6.00 19.00 0.50 5.36 -- -14.97 -94.00 120.00 50 20 \w -60.00 -14.00 0.50 5.36 -- -14.97 0.00 30.00 92 21 \w -79.00 -19.00 0.50 5.36 -- -14.97 -61.00 60.00 120 22 \w -75.00 -2.00 0.50 5.36 -- -14.97 -45.00 90.00 146 23 \w -87.00 -46.00 0.50 5.36 -- -14.97 -77.00 60.00 82 24 \w -91.00 -66.00 0.50 5.36 -- -14.97 0.00 30.00 50 25 \w -66.00 -11.00 0.50 5.36 -- -14.97 125.00 90.00 110 26 \w -68.00 -41.00 0.50 5.36 -- -14.97 134.00 121.00 54 27 \w -58.00 -13.00 0.50 5.36 -- -14.97 125.00 30.00 90 28 \w -88.00 9.00 0.50 5.36 -- -14.97 -30.00 -60.00 194 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at offset/far, HyPix3000' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0113935000 _diffrn_orient_matrix_UB_12 0.0523018000 _diffrn_orient_matrix_UB_13 -0.0021722000 _diffrn_orient_matrix_UB_21 -0.0011604000 _diffrn_orient_matrix_UB_22 0.0063537000 _diffrn_orient_matrix_UB_23 -0.0486501000 _diffrn_orient_matrix_UB_31 -0.0619913000 _diffrn_orient_matrix_UB_32 0.0023078000 _diffrn_orient_matrix_UB_33 0.0001265000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_unetI/netI 0.0393 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.958 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 39514 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.958 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.970 _diffrn_reflns_theta_min 2.083 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic yellowish yellow' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.325 _exptl_crystal_description needle _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.202 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 639 _refine_ls_number_reflns 9568 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0552 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0904P)^2^+0.1031P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1520 _refine_ls_wR_factor_ref 0.1738 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6036 _reflns_number_total 9568 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03725e2.cif _cod_data_source_block extr18 _cod_database_code 7064313 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.991 _shelx_estimated_absorpt_t_min 0.982 _reflns_odcompleteness_completeness 99.72 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C4(H4), C29(H29), C5(H5), C30(H30) 2.b Secondary CH2 refined with riding coordinates: C21(H21A,H21B), C46(H46A,H46B), C31(H31A,H31B), C32(H32A,H32B), C6(H6A,H6B), C33(H33A,H33B), C7(H7A,H7B), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: C19(H19), C44(H44), C41(H41), C43(H43), C42(H42), C18(H18), C16(H16), C22(H22), C17(H17), C9(H9), C34(H34), C47(H47) 2.d X=CH2 refined with riding coordinates: N4(H4A,H4B) 2.e Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C49(H49A,H49B,H49C) ; _shelx_res_file ; TITL extr18_a.res in P-1 extr18.res created by SHELXL-2018/3 at 11:00:30 on 17-Oct-2022 REM Old TITL EXTR18 in P-1 REM SHELXT solution in P-1 REM R1 0.242, Rweak 0.021, Alpha 0.044, Orientation as input REM Formula found by SHELXT: C55 N6 O7 CELL 0.71073 11.5473 13.99 14.7675 80.6 89.223 77.075 ZERR 4 0.0003 0.0004 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 100 92 20 16 L.S. 10 0 0 PLAN 20 SIZE 0.15 0.1 0.2 TEMP 31.75 BOND $H list 4 fmap 2 53 acta OMIT 0 1 1 REM REM REM WGHT 0.090400 0.103100 FVAR 1.18804 O1 4 0.401084 0.726971 0.144154 11.00000 0.06805 0.05498 = 0.06068 -0.00031 0.03044 0.00088 O2 4 0.291418 0.659022 0.339423 11.00000 0.06398 0.06171 = 0.06243 0.00274 0.01252 -0.01326 O6 4 0.197073 1.174769 0.190971 11.00000 0.05851 0.07460 = 0.05914 -0.02324 0.01511 -0.00320 O5 4 0.044570 1.390736 0.132496 11.00000 0.08112 0.07402 = 0.05673 -0.00891 -0.00462 -0.01184 N3 3 0.462409 0.713715 0.349573 11.00000 0.04545 0.05450 = 0.05495 0.00102 0.00324 0.00425 N4 3 0.221983 0.910104 0.425973 11.00000 0.04330 0.08356 = 0.04699 -0.01638 0.01553 -0.00885 AFIX 93 H4A 2 0.168088 0.932653 0.462683 11.00000 -1.20000 H4B 2 0.295282 0.908848 0.437043 11.00000 -1.20000 AFIX 0 N8 3 0.019970 1.193084 0.265010 11.00000 0.05103 0.06941 = 0.05017 -0.01438 0.00780 -0.01732 O3 4 0.270356 1.022109 0.044548 11.00000 0.11895 0.07084 = 0.08305 0.01356 0.04756 0.02446 C20 1 0.401523 0.880365 0.297136 11.00000 0.03747 0.05257 = 0.03969 -0.00358 0.01182 -0.00040 C12 1 0.191826 0.877012 0.351714 11.00000 0.03883 0.05387 = 0.03628 0.00068 0.01013 -0.00240 N1 3 0.491234 0.710406 0.077907 11.00000 0.06906 0.06435 = 0.06792 -0.01042 0.03624 0.00043 N2 3 0.348902 0.967789 0.009347 11.00000 0.07605 0.06996 = 0.05289 0.00529 0.02317 -0.00155 N9 3 0.267252 1.146140 0.435606 11.00000 0.04798 0.08888 = 0.06761 0.01002 -0.00045 -0.00806 O4 4 0.396767 0.995866 -0.060929 11.00000 0.12303 0.09039 = 0.07268 0.01904 0.04778 -0.00196 C15 1 0.497999 0.805078 0.331146 11.00000 0.04142 0.06018 = 0.04747 -0.00515 0.01123 -0.00117 C14 1 0.345433 0.725070 0.329474 11.00000 0.04723 0.05616 = 0.03897 -0.00008 0.01141 -0.00377 C38 1 0.159074 1.273187 0.317121 11.00000 0.03879 0.06158 = 0.04477 -0.01053 0.00969 -0.00974 C3 1 0.341286 0.821556 0.127537 11.00000 0.04442 0.05398 = 0.04254 -0.00473 0.00845 -0.00285 C45 1 0.049517 1.282280 0.375722 11.00000 0.04240 0.05881 = 0.04190 -0.00539 0.00851 -0.00474 C11 1 0.078256 0.875991 0.328407 11.00000 0.03835 0.06196 = 0.04214 -0.00302 0.01308 -0.00161 C2 1 0.387965 0.867134 0.052329 11.00000 0.05288 0.05425 = 0.04070 -0.00589 0.01427 -0.00563 C13 1 0.293914 0.836537 0.291845 11.00000 0.03587 0.05383 = 0.03816 -0.00150 0.00952 -0.00175 C4 1 0.244530 0.852976 0.191147 11.00000 0.04284 0.05781 = 0.03687 -0.00192 0.01098 -0.00131 AFIX 13 H4 2 0.213597 0.924629 0.172556 11.00000 -1.20000 AFIX 0 N5 3 -0.084709 0.942665 0.437115 11.00000 0.05008 0.10565 = 0.07030 -0.02170 0.02568 -0.00909 C39 1 0.131607 1.207077 0.249035 11.00000 0.04679 0.05681 = 0.04501 -0.00540 0.00593 -0.00380 C40 1 -0.031017 1.237766 0.339243 11.00000 0.04488 0.06027 = 0.04325 -0.00228 0.00547 -0.00704 N7 3 -0.060663 1.558149 0.287922 11.00000 0.07175 0.08714 = 0.08256 -0.01855 0.01715 0.00147 O7 4 0.018245 1.555529 0.341396 11.00000 0.10250 0.12078 = 0.12246 -0.06911 -0.01602 0.01574 C10 1 0.042172 0.844047 0.245598 11.00000 0.04092 0.07184 = 0.04785 -0.00240 0.00725 -0.00566 C28 1 0.058422 1.426226 0.209395 11.00000 0.05580 0.06350 = 0.04757 -0.00650 0.00779 -0.01700 C25 1 -0.012533 0.912340 0.388957 11.00000 0.04020 0.07573 = 0.04946 -0.00644 0.01004 -0.00583 C37 1 0.274276 1.221398 0.368953 11.00000 0.04355 0.06947 = 0.04768 -0.01207 0.00775 -0.00781 C19 1 0.414734 0.976595 0.273762 11.00000 0.04986 0.05869 = 0.05056 -0.00165 0.01369 -0.00317 AFIX 43 H19 2 0.350671 1.027469 0.250272 11.00000 -1.20000 AFIX 0 C29 1 0.168033 1.378026 0.266208 11.00000 0.04998 0.06155 = 0.04766 -0.01342 0.01228 -0.01234 AFIX 13 H29 2 0.172459 1.419045 0.313318 11.00000 -1.20000 AFIX 0 C5 1 0.140076 0.802416 0.184824 11.00000 0.04636 0.07492 = 0.04408 -0.00869 0.00746 -0.00851 AFIX 13 H5 2 0.168234 0.731368 0.208409 11.00000 -1.20000 AFIX 0 N6 3 -0.064124 1.442072 0.087055 11.00000 0.08814 0.08427 = 0.07096 0.00507 -0.02315 -0.02079 C30 1 0.280389 1.375612 0.209258 11.00000 0.05438 0.06722 = 0.05577 -0.01770 0.01903 -0.01938 AFIX 13 H30 2 0.278119 1.333380 0.162794 11.00000 -1.20000 AFIX 0 C1 1 0.481959 0.794608 0.023993 11.00000 0.05969 0.06109 = 0.05249 -0.01295 0.02208 -0.01155 C44 1 0.020959 1.328870 0.450518 11.00000 0.05368 0.06995 = 0.04790 -0.01124 0.00966 -0.00928 AFIX 43 H44 2 0.075224 1.357637 0.476001 11.00000 -1.20000 AFIX 0 C35 1 0.388642 1.329962 0.269625 11.00000 0.05282 0.07814 = 0.06053 -0.02715 0.02157 -0.02263 C36 1 0.377634 1.250306 0.344839 11.00000 0.04187 0.07683 = 0.05840 -0.02338 0.00655 -0.00995 C41 1 -0.142308 1.240980 0.375300 11.00000 0.04670 0.08243 = 0.05647 -0.00085 0.00780 -0.01776 AFIX 43 H41 2 -0.196116 1.210888 0.350966 11.00000 -1.20000 AFIX 0 C27 1 -0.038084 1.500306 0.215482 11.00000 0.05465 0.06555 = 0.06142 -0.00466 0.00753 -0.01135 C43 1 -0.091592 1.332054 0.487473 11.00000 0.06105 0.07857 = 0.05070 -0.01158 0.02160 -0.00627 AFIX 43 H43 2 -0.112591 1.362588 0.538581 11.00000 -1.20000 AFIX 0 C42 1 -0.170787 1.290485 0.448781 11.00000 0.04859 0.08568 = 0.05717 0.00103 0.01796 -0.00659 AFIX 43 H42 2 -0.246414 1.295726 0.472765 11.00000 -1.20000 AFIX 0 C18 1 0.524777 0.996037 0.285865 11.00000 0.05937 0.07091 = 0.06715 -0.00958 0.02319 -0.01967 AFIX 43 H18 2 0.535234 1.060635 0.270073 11.00000 -1.20000 AFIX 0 N10 3 0.560914 1.156486 0.444135 11.00000 0.05551 0.15650 = 0.08946 -0.03249 -0.01154 -0.00239 C16 1 0.608325 0.823303 0.342720 11.00000 0.03974 0.08574 = 0.07223 -0.00842 0.00622 -0.00012 AFIX 43 H16 2 0.673102 0.772182 0.364244 11.00000 -1.20000 AFIX 0 O8 4 -0.160968 1.607218 0.292792 11.00000 0.08712 0.16435 = 0.13732 -0.04596 0.01753 0.03953 C50 1 0.480587 1.198901 0.399385 11.00000 0.04651 0.10500 = 0.06746 -0.02921 0.00546 -0.01630 C21 1 0.541532 0.616815 0.377222 11.00000 0.06463 0.06061 = 0.06748 -0.00505 -0.00148 0.00805 AFIX 23 H21A 2 0.612417 0.612943 0.340740 11.00000 -1.20000 H21B 2 0.502401 0.565897 0.364069 11.00000 -1.20000 AFIX 0 C22 1 0.577122 0.595763 0.475720 11.00000 0.08256 0.05743 = 0.06830 -0.00061 -0.00479 -0.00207 AFIX 43 H22 2 0.517874 0.610671 0.517810 11.00000 -1.20000 AFIX 0 C26 1 -0.112339 1.507673 0.137957 11.00000 0.06437 0.07638 = 0.07604 0.00541 -0.00357 -0.02029 C17 1 0.619251 0.920952 0.321033 11.00000 0.04512 0.09161 = 0.07763 -0.01904 0.01655 -0.02084 AFIX 43 H17 2 0.692150 0.936039 0.330483 11.00000 -1.20000 AFIX 0 C46 1 -0.038185 1.137264 0.211195 11.00000 0.07567 0.08041 = 0.06982 -0.01880 0.00049 -0.02895 AFIX 23 H46A 2 -0.063813 1.084877 0.252362 11.00000 -1.20000 H46B 2 0.018778 1.106218 0.169907 11.00000 -1.20000 AFIX 0 C31 1 0.286215 1.479517 0.159396 11.00000 0.08545 0.07607 = 0.07346 -0.01361 0.02571 -0.03231 AFIX 23 H31A 2 0.221148 1.503751 0.114735 11.00000 -1.20000 H31B 2 0.277889 1.525006 0.203326 11.00000 -1.20000 AFIX 0 C24 1 0.566388 0.802310 -0.053204 11.00000 0.09001 0.08096 = 0.07482 -0.01873 0.05171 -0.01295 AFIX 137 H24A 2 0.618509 0.843774 -0.041348 11.00000 -1.50000 H24B 2 0.522398 0.830858 -0.109530 11.00000 -1.50000 H24C 2 0.612430 0.737240 -0.058268 11.00000 -1.50000 AFIX 0 C9 1 -0.070515 0.851478 0.222766 11.00000 0.04479 0.12223 = 0.07398 -0.02470 0.00617 -0.00868 AFIX 43 H9 2 -0.127577 0.876103 0.263228 11.00000 -1.20000 AFIX 0 C34 1 0.489301 1.362339 0.255030 11.00000 0.06096 0.11034 = 0.08296 -0.02697 0.01610 -0.03171 AFIX 43 H34 2 0.554121 1.331711 0.294144 11.00000 -1.20000 AFIX 0 C32 1 0.403580 1.476299 0.111174 11.00000 0.09308 0.09021 = 0.08548 -0.02174 0.03110 -0.04843 AFIX 23 H32A 2 0.412602 1.429996 0.067954 11.00000 -1.20000 H32B 2 0.404426 1.541597 0.077161 11.00000 -1.20000 AFIX 0 C47 1 -0.142022 1.200974 0.157019 11.00000 0.08676 0.11130 = 0.06229 -0.01872 -0.00777 -0.03517 AFIX 43 H47 2 -0.131758 1.259568 0.121288 11.00000 -1.20000 AFIX 0 C6 1 0.094258 0.812832 0.086758 11.00000 0.07222 0.13316 = 0.04875 -0.01860 0.00587 -0.03070 AFIX 23 H6A 2 0.075278 0.882447 0.059027 11.00000 -1.20000 H6B 2 0.155458 0.777658 0.050926 11.00000 -1.20000 AFIX 0 C33 1 0.504536 1.444482 0.180031 11.00000 0.09001 0.12185 = 0.10440 -0.03414 0.04293 -0.06171 AFIX 23 H33A 2 0.512421 1.501343 0.207276 11.00000 -1.20000 H33B 2 0.577550 1.422610 0.148559 11.00000 -1.20000 AFIX 0 C7 1 -0.016143 0.770559 0.085944 11.00000 0.07528 0.15849 = 0.06712 -0.03300 0.00024 -0.03777 AFIX 23 H7A 2 -0.043117 0.775999 0.023002 11.00000 -1.20000 H7B 2 0.003641 0.700625 0.112582 11.00000 -1.20000 AFIX 0 C23 1 0.684599 0.558118 0.507843 11.00000 0.10301 0.07649 = 0.09598 0.00034 -0.03565 -0.00130 C8 1 -0.113924 0.824145 0.138667 11.00000 0.06272 0.16313 = 0.09300 -0.03374 -0.00893 -0.02455 AFIX 23 H8A 2 -0.155973 0.884058 0.099435 11.00000 -1.20000 H8B 2 -0.169880 0.782269 0.155727 11.00000 -1.20000 AFIX 0 C49 1 -0.228991 1.576287 0.108523 11.00000 0.07639 0.11519 = 0.13683 0.00664 -0.03388 -0.00848 AFIX 137 H49A 2 -0.258843 1.558132 0.054943 11.00000 -1.50000 H49B 2 -0.218735 1.643308 0.094515 11.00000 -1.50000 H49C 2 -0.284455 1.571571 0.157171 11.00000 -1.50000 AFIX 0 C48 1 -0.246728 1.180990 0.155716 11.00000 0.09068 0.21820 = 0.09810 -0.04642 -0.01320 -0.04161 H23A 2 0.696610 0.544003 0.583040 11.00000 0.13172 H23B 2 0.754540 0.541568 0.455437 11.00000 0.10636 H9A 2 0.322213 1.116453 0.464035 11.00000 0.07566 H9B 2 0.199113 1.131733 0.454473 11.00000 0.06942 H48A 2 -0.304105 1.237552 0.105977 11.00000 0.16792 H48B 2 -0.248416 1.108189 0.192610 11.00000 0.26007 HKLF 4 REM extr18_a.res in P-1 REM wR2 = 0.1738, GooF = S = 1.076, Restrained GooF = 1.076 for all data REM R1 = 0.0552 for 6036 Fo > 4sig(Fo) and 0.0890 for all 9568 data REM 639 parameters refined using 0 restraints END WGHT 0.0904 0.1016 REM Highest difference peak 0.202, deepest hole -0.262, 1-sigma level 0.044 Q1 1 0.3200 0.9633 -0.0828 11.00000 0.05 0.20 Q2 1 0.2136 0.9767 0.0104 11.00000 0.05 0.20 Q3 1 0.5249 0.7469 -0.1179 11.00000 0.05 0.18 Q4 1 -0.1151 0.9080 0.1215 11.00000 0.05 0.17 Q5 1 0.5327 1.3133 0.3065 11.00000 0.05 0.17 Q6 1 0.5721 0.8845 -0.0794 11.00000 0.05 0.17 Q7 1 -0.1987 0.8231 0.1182 11.00000 0.05 0.17 Q8 1 0.3479 0.8638 0.2966 11.00000 0.05 0.16 Q9 1 0.6677 0.7472 -0.0207 11.00000 0.05 0.16 Q10 1 0.5724 1.4356 0.2390 11.00000 0.05 0.15 Q11 1 0.4790 1.1359 0.4214 11.00000 0.05 0.15 Q12 1 0.4102 1.2016 0.3660 11.00000 0.05 0.15 Q13 1 0.2711 0.8425 0.2482 11.00000 0.05 0.15 Q14 1 0.5620 1.0762 0.4651 11.00000 0.05 0.15 Q15 1 -0.1352 0.9457 0.0602 11.00000 0.05 0.15 Q16 1 -0.0712 0.9280 0.2085 11.00000 0.05 0.15 Q17 1 -0.2241 1.6569 0.1386 11.00000 0.05 0.14 Q18 1 -0.2027 1.5182 0.2909 11.00000 0.05 0.14 Q19 1 -0.0203 0.9045 0.2159 11.00000 0.05 0.14 Q20 1 0.0007 1.1730 0.2473 11.00000 0.05 0.14 ; _shelx_res_checksum 18049 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.410 _oxdiff_exptl_absorpt_empirical_full_min 0.628 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40108(13) 0.72697(10) 0.14415(10) 0.0649(4) Uani 1 1 d . . . . . O2 O 0.29142(13) 0.65902(11) 0.33942(10) 0.0644(4) Uani 1 1 d . . . . . O6 O 0.19707(12) 1.17477(11) 0.19097(10) 0.0647(4) Uani 1 1 d . . . . . O5 O 0.04457(14) 1.39074(12) 0.13250(10) 0.0717(4) Uani 1 1 d . . . . . N3 N 0.46241(14) 0.71371(12) 0.34957(11) 0.0553(4) Uani 1 1 d . . . . . N4 N 0.22198(14) 0.91010(13) 0.42597(11) 0.0583(4) Uani 1 1 d . . . . . H4A H 0.168088 0.932653 0.462683 0.070 Uiso 1 1 calc R . . . . H4B H 0.295282 0.908848 0.437043 0.070 Uiso 1 1 calc R . . . . N8 N 0.01997(14) 1.19308(13) 0.26501(11) 0.0558(4) Uani 1 1 d . . . . . O3 O 0.27036(18) 1.02211(13) 0.04455(13) 0.1017(7) Uani 1 1 d . . . . . C20 C 0.40152(15) 0.88036(14) 0.29714(12) 0.0454(4) Uani 1 1 d . . . . . C12 C 0.19183(15) 0.87701(14) 0.35171(12) 0.0453(4) Uani 1 1 d . . . . . N1 N 0.49123(16) 0.71041(14) 0.07791(13) 0.0699(5) Uani 1 1 d . . . . . N2 N 0.34890(17) 0.96779(14) 0.00935(13) 0.0706(5) Uani 1 1 d . . . . . N9 N 0.2673(2) 1.14614(17) 0.43561(15) 0.0719(6) Uani 1 1 d . . . . . O4 O 0.39677(18) 0.99587(14) -0.06093(12) 0.1030(7) Uani 1 1 d . . . . . C15 C 0.49800(16) 0.80508(15) 0.33115(13) 0.0518(5) Uani 1 1 d . . . . . C14 C 0.34543(17) 0.72507(15) 0.32947(13) 0.0497(5) Uani 1 1 d . . . . . C38 C 0.15907(15) 1.27319(15) 0.31712(13) 0.0485(5) Uani 1 1 d . . . . . C3 C 0.34129(16) 0.82156(14) 0.12754(13) 0.0487(5) Uani 1 1 d . . . . . C45 C 0.04952(16) 1.28228(14) 0.37572(13) 0.0492(5) Uani 1 1 d . . . . . C11 C 0.07826(15) 0.87599(14) 0.32841(13) 0.0498(5) Uani 1 1 d . . . . . C2 C 0.38796(17) 0.86713(14) 0.05233(13) 0.0506(5) Uani 1 1 d . . . . . C13 C 0.29391(15) 0.83654(14) 0.29185(12) 0.0447(4) Uani 1 1 d . . . . . C4 C 0.24453(15) 0.85298(15) 0.19115(12) 0.0482(5) Uani 1 1 d . . . . . H4 H 0.213597 0.924629 0.172556 0.058 Uiso 1 1 calc R . . . . N5 N -0.08471(15) 0.94266(16) 0.43712(14) 0.0761(6) Uani 1 1 d . . . . . C39 C 0.13161(17) 1.20708(15) 0.24904(13) 0.0512(5) Uani 1 1 d . . . . . C40 C -0.03102(16) 1.23777(15) 0.33924(13) 0.0510(5) Uani 1 1 d . . . . . N7 N -0.0607(2) 1.55815(16) 0.28792(17) 0.0832(6) Uani 1 1 d . . . . . O7 O 0.0182(2) 1.55553(16) 0.34140(16) 0.1159(8) Uani 1 1 d . . . . . C10 C 0.04217(16) 0.84405(16) 0.24560(14) 0.0556(5) Uani 1 1 d . . . . . C28 C 0.05842(18) 1.42623(16) 0.20940(14) 0.0554(5) Uani 1 1 d . . . . . C25 C -0.01253(16) 0.91234(16) 0.38896(14) 0.0568(5) Uani 1 1 d . . . . . C37 C 0.27428(16) 1.22140(16) 0.36895(14) 0.0541(5) Uani 1 1 d . . . . . C19 C 0.41473(17) 0.97660(15) 0.27376(13) 0.0554(5) Uani 1 1 d . . . . . H19 H 0.350671 1.027469 0.250272 0.067 Uiso 1 1 calc R . . . . C29 C 0.16803(16) 1.37803(15) 0.26621(13) 0.0527(5) Uani 1 1 d . . . . . H29 H 0.172459 1.419045 0.313318 0.063 Uiso 1 1 calc R . . . . C5 C 0.14008(16) 0.80242(17) 0.18482(13) 0.0561(5) Uani 1 1 d . . . . . H5 H 0.168234 0.731368 0.208409 0.067 Uiso 1 1 calc R . . . . N6 N -0.0641(2) 1.44207(17) 0.08705(15) 0.0827(6) Uani 1 1 d . . . . . C30 C 0.28039(17) 1.37561(16) 0.20926(15) 0.0575(5) Uani 1 1 d . . . . . H30 H 0.278119 1.333380 0.162794 0.069 Uiso 1 1 calc R . . . . C1 C 0.48196(18) 0.79461(16) 0.02399(14) 0.0579(5) Uani 1 1 d . . . . . C44 C 0.02096(18) 1.32887(16) 0.45052(14) 0.0578(5) Uani 1 1 d . . . . . H44 H 0.075224 1.357637 0.476001 0.069 Uiso 1 1 calc R . . . . C35 C 0.38864(18) 1.32996(17) 0.26962(15) 0.0610(6) Uani 1 1 d . . . . . C36 C 0.37763(17) 1.25031(16) 0.34484(15) 0.0582(5) Uani 1 1 d . . . . . C41 C -0.14231(18) 1.24098(17) 0.37530(15) 0.0626(6) Uani 1 1 d . . . . . H41 H -0.196116 1.210888 0.350966 0.075 Uiso 1 1 calc R . . . . C27 C -0.03808(18) 1.50031(16) 0.21548(15) 0.0616(6) Uani 1 1 d . . . . . C43 C -0.0916(2) 1.33205(17) 0.48747(15) 0.0650(6) Uani 1 1 d . . . . . H43 H -0.112591 1.362588 0.538581 0.078 Uiso 1 1 calc R . . . . C42 C -0.17079(19) 1.29048(18) 0.44878(16) 0.0668(6) Uani 1 1 d . . . . . H42 H -0.246414 1.295726 0.472765 0.080 Uiso 1 1 calc R . . . . C18 C 0.52478(19) 0.99604(18) 0.28586(15) 0.0654(6) Uani 1 1 d . . . . . H18 H 0.535234 1.060635 0.270073 0.078 Uiso 1 1 calc R . . . . N10 N 0.56091(19) 1.1565(2) 0.44414(17) 0.1024(8) Uani 1 1 d . . . . . C16 C 0.60833(18) 0.82330(19) 0.34272(16) 0.0687(6) Uani 1 1 d . . . . . H16 H 0.673102 0.772182 0.364244 0.082 Uiso 1 1 calc R . . . . O8 O -0.16097(19) 1.6072(2) 0.29279(18) 0.1381(9) Uani 1 1 d . . . . . C50 C 0.4806(2) 1.1989(2) 0.39939(17) 0.0714(7) Uani 1 1 d . . . . . C21 C 0.5415(2) 0.61681(16) 0.37722(16) 0.0684(6) Uani 1 1 d . . . . . H21A H 0.612417 0.612943 0.340740 0.082 Uiso 1 1 calc R . . . . H21B H 0.502401 0.565897 0.364069 0.082 Uiso 1 1 calc R . . . . C22 C 0.5771(2) 0.59576(16) 0.47572(17) 0.0727(6) Uani 1 1 d . . . . . H22 H 0.517874 0.610671 0.517810 0.087 Uiso 1 1 calc R . . . . C26 C -0.1123(2) 1.50767(19) 0.13796(19) 0.0736(7) Uani 1 1 d . . . . . C17 C 0.61925(19) 0.92095(19) 0.32103(17) 0.0701(6) Uani 1 1 d . . . . . H17 H 0.692150 0.936039 0.330483 0.084 Uiso 1 1 calc R . . . . C46 C -0.0382(2) 1.13726(18) 0.21120(17) 0.0727(6) Uani 1 1 d . . . . . H46A H -0.063813 1.084877 0.252362 0.087 Uiso 1 1 calc R . . . . H46B H 0.018778 1.106218 0.169907 0.087 Uiso 1 1 calc R . . . . C31 C 0.2862(2) 1.47952(18) 0.15940(18) 0.0761(7) Uani 1 1 d . . . . . H31A H 0.221148 1.503751 0.114735 0.091 Uiso 1 1 calc R . . . . H31B H 0.277889 1.525006 0.203326 0.091 Uiso 1 1 calc R . . . . C24 C 0.5664(2) 0.80231(19) -0.05320(17) 0.0827(8) Uani 1 1 d . . . . . H24A H 0.618509 0.843774 -0.041348 0.124 Uiso 1 1 calc GR . . . . H24B H 0.522398 0.830858 -0.109530 0.124 Uiso 1 1 calc GR . . . . H24C H 0.612430 0.737240 -0.058268 0.124 Uiso 1 1 calc GR . . . . C9 C -0.07051(19) 0.8515(2) 0.22277(18) 0.0810(7) Uani 1 1 d . . . . . H9 H -0.127577 0.876103 0.263228 0.097 Uiso 1 1 calc R . . . . C34 C 0.4893(2) 1.3623(2) 0.25503(19) 0.0816(7) Uani 1 1 d . . . . . H34 H 0.554121 1.331711 0.294144 0.098 Uiso 1 1 calc R . . . . C32 C 0.4036(2) 1.4763(2) 0.1112(2) 0.0846(8) Uani 1 1 d . . . . . H32A H 0.412602 1.429996 0.067954 0.102 Uiso 1 1 calc R . . . . H32B H 0.404426 1.541597 0.077161 0.102 Uiso 1 1 calc R . . . . C47 C -0.1420(2) 1.2010(2) 0.15702(17) 0.0841(8) Uani 1 1 d . . . . . H47 H -0.131758 1.259568 0.121288 0.101 Uiso 1 1 calc R . . . . C6 C 0.0943(2) 0.8128(2) 0.08676(16) 0.0831(8) Uani 1 1 d . . . . . H6A H 0.075278 0.882447 0.059027 0.100 Uiso 1 1 calc R . . . . H6B H 0.155458 0.777658 0.050926 0.100 Uiso 1 1 calc R . . . . C33 C 0.5045(3) 1.4445(2) 0.1800(2) 0.0980(9) Uani 1 1 d . . . . . H33A H 0.512421 1.501343 0.207276 0.118 Uiso 1 1 calc R . . . . H33B H 0.577550 1.422610 0.148559 0.118 Uiso 1 1 calc R . . . . C7 C -0.0161(2) 0.7706(3) 0.0859(2) 0.0968(9) Uani 1 1 d . . . . . H7A H -0.043117 0.775999 0.023002 0.116 Uiso 1 1 calc R . . . . H7B H 0.003641 0.700625 0.112582 0.116 Uiso 1 1 calc R . . . . C23 C 0.6846(3) 0.5581(2) 0.5078(3) 0.0961(9) Uani 1 1 d . . . . . C8 C -0.1139(2) 0.8241(3) 0.1387(2) 0.1049(10) Uani 1 1 d . . . . . H8A H -0.155973 0.884058 0.099435 0.126 Uiso 1 1 calc R . . . . H8B H -0.169880 0.782269 0.155727 0.126 Uiso 1 1 calc R . . . . C49 C -0.2290(2) 1.5763(2) 0.1085(2) 0.1143(11) Uani 1 1 d . . . . . H49A H -0.258843 1.558132 0.054943 0.172 Uiso 1 1 calc GR . . . . H49B H -0.218735 1.643308 0.094515 0.172 Uiso 1 1 calc GR . . . . H49C H -0.284455 1.571571 0.157171 0.172 Uiso 1 1 calc GR . . . . C48 C -0.2467(3) 1.1810(5) 0.1557(3) 0.1321(16) Uani 1 1 d . . . . . H23A H 0.697(3) 0.544(2) 0.583(2) 0.132(11) Uiso 1 1 d . . . . . H23B H 0.755(2) 0.542(2) 0.455(2) 0.106(10) Uiso 1 1 d . . . . . H9A H 0.322(2) 1.1165(18) 0.4640(18) 0.076(8) Uiso 1 1 d . . . . . H9B H 0.199(2) 1.1317(16) 0.4545(15) 0.069(7) Uiso 1 1 d . . . . . H48A H -0.304(3) 1.238(3) 0.106(3) 0.168(15) Uiso 1 1 d . . . . . H48B H -0.248(5) 1.108(4) 0.193(4) 0.26(3) Uiso 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0680(9) 0.0550(9) 0.0607(9) -0.0003(7) 0.0304(7) 0.0009(7) O2 0.0640(9) 0.0617(9) 0.0624(9) 0.0027(7) 0.0125(7) -0.0133(7) O6 0.0585(8) 0.0746(10) 0.0591(9) -0.0232(7) 0.0151(7) -0.0032(7) O5 0.0811(11) 0.0740(10) 0.0567(9) -0.0089(8) -0.0046(8) -0.0118(8) N3 0.0454(9) 0.0545(10) 0.0550(10) 0.0010(8) 0.0032(7) 0.0042(7) N4 0.0433(9) 0.0836(12) 0.0470(10) -0.0164(9) 0.0155(7) -0.0089(8) N8 0.0510(9) 0.0694(11) 0.0502(10) -0.0144(8) 0.0078(8) -0.0173(8) O3 0.1189(14) 0.0708(11) 0.0830(12) 0.0136(9) 0.0476(11) 0.0245(10) C20 0.0375(9) 0.0526(11) 0.0397(10) -0.0036(8) 0.0118(8) -0.0004(8) C12 0.0388(10) 0.0539(11) 0.0363(10) 0.0007(8) 0.0101(8) -0.0024(8) N1 0.0691(12) 0.0644(12) 0.0679(12) -0.0104(10) 0.0362(10) 0.0004(9) N2 0.0760(13) 0.0700(12) 0.0529(11) 0.0053(9) 0.0232(10) -0.0015(10) N9 0.0480(12) 0.0889(16) 0.0676(14) 0.0100(11) -0.0005(10) -0.0081(11) O4 0.1230(15) 0.0904(13) 0.0727(12) 0.0190(10) 0.0478(11) -0.0020(11) C15 0.0414(10) 0.0602(13) 0.0475(11) -0.0052(9) 0.0112(8) -0.0012(9) C14 0.0472(11) 0.0562(12) 0.0390(10) -0.0001(9) 0.0114(8) -0.0038(9) C38 0.0388(10) 0.0616(12) 0.0448(11) -0.0105(9) 0.0097(8) -0.0097(8) C3 0.0444(10) 0.0540(12) 0.0425(11) -0.0047(9) 0.0084(8) -0.0028(9) C45 0.0424(10) 0.0588(12) 0.0419(10) -0.0054(9) 0.0085(8) -0.0047(9) C11 0.0383(10) 0.0620(12) 0.0421(11) -0.0030(9) 0.0131(8) -0.0016(8) C2 0.0529(11) 0.0543(12) 0.0407(10) -0.0059(9) 0.0143(9) -0.0056(9) C13 0.0359(9) 0.0538(11) 0.0382(10) -0.0015(8) 0.0095(7) -0.0018(8) C4 0.0428(10) 0.0578(12) 0.0369(10) -0.0019(8) 0.0110(8) -0.0013(8) N5 0.0501(10) 0.1056(16) 0.0703(13) -0.0217(11) 0.0257(9) -0.0091(10) C39 0.0468(11) 0.0568(12) 0.0450(11) -0.0054(9) 0.0059(9) -0.0038(9) C40 0.0449(10) 0.0603(12) 0.0433(11) -0.0023(9) 0.0055(8) -0.0070(9) N7 0.0718(14) 0.0871(16) 0.0826(16) -0.0185(12) 0.0171(12) 0.0015(12) O7 0.1025(15) 0.1208(17) 0.1225(18) -0.0691(15) -0.0160(14) 0.0157(13) C10 0.0409(10) 0.0718(14) 0.0478(12) -0.0024(10) 0.0072(9) -0.0057(9) C28 0.0558(12) 0.0635(13) 0.0476(12) -0.0065(10) 0.0078(9) -0.0170(10) C25 0.0402(10) 0.0757(14) 0.0495(12) -0.0064(10) 0.0100(9) -0.0058(9) C37 0.0436(11) 0.0695(14) 0.0477(11) -0.0121(10) 0.0077(9) -0.0078(9) C19 0.0499(11) 0.0587(13) 0.0506(12) -0.0017(9) 0.0137(9) -0.0032(9) C29 0.0500(11) 0.0615(12) 0.0477(11) -0.0134(9) 0.0123(9) -0.0123(9) C5 0.0464(11) 0.0749(14) 0.0441(11) -0.0087(10) 0.0075(9) -0.0085(10) N6 0.0881(15) 0.0843(15) 0.0710(14) 0.0051(12) -0.0231(12) -0.0208(12) C30 0.0544(12) 0.0672(13) 0.0558(12) -0.0177(10) 0.0190(10) -0.0194(10) C1 0.0597(12) 0.0611(13) 0.0525(12) -0.0130(10) 0.0221(10) -0.0116(10) C44 0.0537(12) 0.0700(14) 0.0479(12) -0.0112(10) 0.0097(9) -0.0093(10) C35 0.0528(12) 0.0781(15) 0.0605(13) -0.0272(11) 0.0216(10) -0.0226(11) C36 0.0419(11) 0.0768(15) 0.0584(13) -0.0234(11) 0.0066(9) -0.0100(10) C41 0.0467(11) 0.0824(15) 0.0565(13) -0.0008(11) 0.0078(10) -0.0178(10) C27 0.0547(12) 0.0656(14) 0.0614(14) -0.0047(11) 0.0075(10) -0.0113(10) C43 0.0610(13) 0.0786(15) 0.0507(12) -0.0116(11) 0.0216(10) -0.0063(11) C42 0.0486(12) 0.0857(16) 0.0572(14) 0.0010(12) 0.0180(10) -0.0066(11) C18 0.0594(14) 0.0709(15) 0.0671(15) -0.0096(12) 0.0232(11) -0.0197(11) N10 0.0555(13) 0.156(2) 0.0895(16) -0.0325(16) -0.0115(12) -0.0024(14) C16 0.0397(11) 0.0857(17) 0.0722(15) -0.0084(13) 0.0062(10) -0.0001(11) O8 0.0871(14) 0.164(2) 0.137(2) -0.0460(17) 0.0175(13) 0.0395(14) C50 0.0465(13) 0.1050(19) 0.0675(15) -0.0292(14) 0.0055(11) -0.0163(12) C21 0.0646(14) 0.0606(14) 0.0675(15) -0.0051(11) -0.0015(11) 0.0081(11) C22 0.0826(17) 0.0574(14) 0.0683(16) -0.0006(11) -0.0048(13) -0.0021(12) C26 0.0644(15) 0.0764(16) 0.0760(17) 0.0054(14) -0.0036(13) -0.0203(12) C17 0.0451(12) 0.0916(18) 0.0776(16) -0.0190(13) 0.0165(11) -0.0208(12) C46 0.0757(16) 0.0804(16) 0.0698(16) -0.0188(13) 0.0005(12) -0.0290(13) C31 0.0854(17) 0.0761(16) 0.0735(16) -0.0136(13) 0.0257(13) -0.0323(13) C24 0.0900(17) 0.0810(17) 0.0748(16) -0.0187(13) 0.0517(14) -0.0130(13) C9 0.0448(13) 0.122(2) 0.0740(17) -0.0247(15) 0.0062(11) -0.0087(13) C34 0.0610(14) 0.110(2) 0.0830(18) -0.0270(15) 0.0161(13) -0.0317(14) C32 0.0931(19) 0.0902(19) 0.0855(18) -0.0217(15) 0.0311(16) -0.0484(15) C47 0.0868(19) 0.111(2) 0.0623(16) -0.0187(14) -0.0078(14) -0.0352(16) C6 0.0722(15) 0.133(2) 0.0487(14) -0.0186(14) 0.0059(11) -0.0307(15) C33 0.090(2) 0.122(2) 0.104(2) -0.0341(19) 0.0429(18) -0.0617(18) C7 0.0753(17) 0.158(3) 0.0671(17) -0.0330(18) 0.0002(14) -0.0378(18) C23 0.103(2) 0.0765(19) 0.096(2) 0.0003(16) -0.036(2) -0.0013(16) C8 0.0627(16) 0.163(3) 0.093(2) -0.034(2) -0.0089(15) -0.0246(17) C49 0.0764(19) 0.115(2) 0.137(3) 0.007(2) -0.0339(19) -0.0085(17) C48 0.091(2) 0.218(5) 0.098(3) -0.046(3) -0.013(2) -0.042(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 N1 109.61(14) . . ? C28 O5 N6 110.48(17) . . ? C15 N3 C21 125.32(17) . . ? C14 N3 C15 111.72(16) . . ? C14 N3 C21 122.65(18) . . ? H4A N4 H4B 120.0 . . ? C12 N4 H4A 120.0 . . ? C12 N4 H4B 120.0 . . ? C39 N8 C40 111.76(16) . . ? C39 N8 C46 123.32(18) . . ? C40 N8 C46 124.92(17) . . ? C15 C20 C13 109.07(16) . . ? C19 C20 C15 120.10(18) . . ? C19 C20 C13 130.83(16) . . ? N4 C12 C11 124.30(16) . . ? N4 C12 C13 116.13(15) . . ? C11 C12 C13 119.57(17) . . ? C1 N1 O1 105.94(15) . . ? O3 N2 O4 123.0(2) . . ? O3 N2 C2 118.79(17) . . ? O4 N2 C2 118.22(18) . . ? C37 N9 H9A 121(2) . . ? C37 N9 H9B 123.3(15) . . ? H9A N9 H9B 115(2) . . ? C20 C15 N3 109.49(16) . . ? C16 C15 N3 128.68(19) . . ? C16 C15 C20 121.8(2) . . ? O2 C14 N3 125.56(18) . . ? O2 C14 C13 126.53(17) . . ? N3 C14 C13 107.91(17) . . ? C45 C38 C39 101.56(15) . . ? C45 C38 C29 109.80(15) . . ? C39 C38 C29 111.42(16) . . ? C37 C38 C45 114.53(15) . . ? C37 C38 C39 108.93(15) . . ? C37 C38 C29 110.33(15) . . ? O1 C3 C2 107.66(16) . . ? O1 C3 C4 117.14(16) . . ? C2 C3 C4 135.20(18) . . ? C40 C45 C38 108.85(16) . . ? C44 C45 C38 130.61(18) . . ? C44 C45 C40 120.46(18) . . ? C12 C11 C10 125.42(16) . . ? C12 C11 C25 116.59(18) . . ? C25 C11 C10 117.96(17) . . ? C3 C2 N2 126.49(17) . . ? C3 C2 C1 106.80(18) . . ? C1 C2 N2 126.70(17) . . ? C20 C13 C12 114.14(15) . . ? C20 C13 C14 101.80(14) . . ? C20 C13 C4 111.60(14) . . ? C12 C13 C14 109.30(14) . . ? C12 C13 C4 107.89(14) . . ? C14 C13 C4 112.09(15) . . ? C3 C4 C13 110.89(14) . . ? C3 C4 H4 107.2 . . ? C3 C4 C5 112.55(16) . . ? C13 C4 H4 107.2 . . ? C5 C4 C13 111.60(15) . . ? C5 C4 H4 107.2 . . ? O6 C39 N8 125.85(19) . . ? O6 C39 C38 126.29(18) . . ? N8 C39 C38 107.85(15) . . ? C45 C40 N8 109.64(16) . . ? C41 C40 N8 129.03(19) . . ? C41 C40 C45 121.33(19) . . ? O7 N7 C27 119.7(2) . . ? O7 N7 O8 123.0(2) . . ? O8 N7 C27 117.3(3) . . ? C11 C10 C5 116.83(16) . . ? C9 C10 C11 122.94(19) . . ? C9 C10 C5 120.2(2) . . ? O5 C28 C29 116.89(18) . . ? O5 C28 C27 107.16(19) . . ? C27 C28 C29 135.9(2) . . ? N5 C25 C11 179.0(2) . . ? N9 C37 C38 115.70(18) . . ? N9 C37 C36 123.9(2) . . ? C36 C37 C38 120.35(19) . . ? C20 C19 H19 120.7 . . ? C20 C19 C18 118.65(19) . . ? C18 C19 H19 120.7 . . ? C38 C29 H29 107.1 . . ? C28 C29 C38 110.57(16) . . ? C28 C29 H29 107.1 . . ? C28 C29 C30 111.62(16) . . ? C30 C29 C38 112.88(16) . . ? C30 C29 H29 107.1 . . ? C4 C5 H5 107.9 . . ? C10 C5 C4 109.22(17) . . ? C10 C5 H5 107.9 . . ? C10 C5 C6 111.03(17) . . ? C6 C5 C4 112.70(17) . . ? C6 C5 H5 107.9 . . ? C26 N6 O5 105.26(19) . . ? C29 C30 H30 108.0 . . ? C29 C30 C31 111.69(17) . . ? C35 C30 C29 109.89(17) . . ? C35 C30 H30 108.0 . . ? C35 C30 C31 111.06(18) . . ? C31 C30 H30 108.0 . . ? N1 C1 C2 109.99(17) . . ? N1 C1 C24 119.14(19) . . ? C2 C1 C24 130.9(2) . . ? C45 C44 H44 120.8 . . ? C45 C44 C43 118.4(2) . . ? C43 C44 H44 120.8 . . ? C36 C35 C30 116.72(17) . . ? C34 C35 C30 120.8(2) . . ? C34 C35 C36 122.5(2) . . ? C37 C36 C35 125.01(19) . . ? C37 C36 C50 116.1(2) . . ? C50 C36 C35 118.86(19) . . ? C40 C41 H41 121.3 . . ? C42 C41 C40 117.5(2) . . ? C42 C41 H41 121.3 . . ? C28 C27 N7 126.0(2) . . ? C28 C27 C26 106.9(2) . . ? C26 C27 N7 127.0(2) . . ? C44 C43 H43 119.9 . . ? C42 C43 C44 120.2(2) . . ? C42 C43 H43 119.9 . . ? C41 C42 H42 118.9 . . ? C43 C42 C41 122.11(19) . . ? C43 C42 H42 118.9 . . ? C19 C18 H18 119.7 . . ? C17 C18 C19 120.7(2) . . ? C17 C18 H18 119.7 . . ? C15 C16 H16 121.4 . . ? C15 C16 C17 117.3(2) . . ? C17 C16 H16 121.4 . . ? N10 C50 C36 178.2(3) . . ? N3 C21 H21A 108.8 . . ? N3 C21 H21B 108.8 . . ? N3 C21 C22 113.61(19) . . ? H21A C21 H21B 107.7 . . ? C22 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? C21 C22 H22 117.5 . . ? C23 C22 C21 125.1(3) . . ? C23 C22 H22 117.5 . . ? N6 C26 C27 110.2(2) . . ? N6 C26 C49 119.2(3) . . ? C27 C26 C49 130.6(3) . . ? C18 C17 C16 121.5(2) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? N8 C46 H46A 109.1 . . ? N8 C46 H46B 109.1 . . ? N8 C46 C47 112.5(2) . . ? H46A C46 H46B 107.8 . . ? C47 C46 H46A 109.1 . . ? C47 C46 H46B 109.1 . . ? C30 C31 H31A 109.6 . . ? C30 C31 H31B 109.6 . . ? H31A C31 H31B 108.1 . . ? C32 C31 C30 110.4(2) . . ? C32 C31 H31A 109.6 . . ? C32 C31 H31B 109.6 . . ? C1 C24 H24A 109.5 . . ? C1 C24 H24B 109.5 . . ? C1 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 C9 H9 117.0 . . ? C10 C9 C8 126.0(2) . . ? C8 C9 H9 117.0 . . ? C35 C34 H34 117.7 . . ? C35 C34 C33 124.5(3) . . ? C33 C34 H34 117.7 . . ? C31 C32 H32A 109.6 . . ? C31 C32 H32B 109.6 . . ? H32A C32 H32B 108.2 . . ? C33 C32 C31 110.1(2) . . ? C33 C32 H32A 109.6 . . ? C33 C32 H32B 109.6 . . ? C46 C47 H47 117.6 . . ? C48 C47 C46 124.7(4) . . ? C48 C47 H47 117.6 . . ? C5 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C7 C6 C5 110.2(2) . . ? C7 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C34 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C32 C33 C34 113.5(2) . . ? C32 C33 H33A 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C6 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C8 C7 C6 111.5(2) . . ? C8 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C22 C23 H23A 116.6(17) . . ? C22 C23 H23B 116.0(14) . . ? H23A C23 H23B 127(2) . . ? C9 C8 C7 112.9(2) . . ? C9 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8A 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C26 C49 H49A 109.5 . . ? C26 C49 H49B 109.5 . . ? C26 C49 H49C 109.5 . . ? H49A C49 H49B 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C47 C48 H48A 109(2) . . ? C47 C48 H48B 113(3) . . ? H48A C48 H48B 137(4) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.426(2) . ? O1 C3 1.333(2) . ? O2 C14 1.215(2) . ? O6 C39 1.211(2) . ? O5 C28 1.337(2) . ? O5 N6 1.415(2) . ? N3 C15 1.412(3) . ? N3 C14 1.355(2) . ? N3 C21 1.454(2) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N4 C12 1.337(2) . ? N8 C39 1.358(2) . ? N8 C40 1.407(2) . ? N8 C46 1.464(3) . ? O3 N2 1.216(2) . ? C20 C15 1.386(2) . ? C20 C13 1.512(3) . ? C20 C19 1.376(3) . ? C12 C11 1.364(3) . ? C12 C13 1.526(2) . ? N1 C1 1.293(3) . ? N2 O4 1.219(2) . ? N2 C2 1.422(3) . ? N9 C37 1.335(3) . ? N9 H9A 0.76(3) . ? N9 H9B 0.89(2) . ? C15 C16 1.372(3) . ? C14 C13 1.551(3) . ? C38 C45 1.517(2) . ? C38 C39 1.553(3) . ? C38 C37 1.515(3) . ? C38 C29 1.560(3) . ? C3 C2 1.355(3) . ? C3 C4 1.487(2) . ? C45 C40 1.387(3) . ? C45 C44 1.372(3) . ? C11 C10 1.464(3) . ? C11 C25 1.429(2) . ? C2 C1 1.420(3) . ? C13 C4 1.563(3) . ? C4 H4 0.9800 . ? C4 C5 1.540(3) . ? N5 C25 1.142(2) . ? C40 C41 1.379(3) . ? N7 O7 1.204(3) . ? N7 C27 1.431(3) . ? N7 O8 1.215(3) . ? C10 C5 1.507(3) . ? C10 C9 1.326(3) . ? C28 C29 1.491(3) . ? C28 C27 1.355(3) . ? C37 C36 1.368(3) . ? C19 H19 0.9300 . ? C19 C18 1.377(3) . ? C29 H29 0.9800 . ? C29 C30 1.534(3) . ? C5 H5 0.9800 . ? C5 C6 1.522(3) . ? N6 C26 1.305(3) . ? C30 H30 0.9800 . ? C30 C35 1.501(3) . ? C30 C31 1.534(3) . ? C1 C24 1.496(3) . ? C44 H44 0.9300 . ? C44 C43 1.397(3) . ? C35 C36 1.465(3) . ? C35 C34 1.341(3) . ? C36 C50 1.426(3) . ? C41 H41 0.9300 . ? C41 C42 1.378(3) . ? C27 C26 1.416(3) . ? C43 H43 0.9300 . ? C43 C42 1.364(3) . ? C42 H42 0.9300 . ? C18 H18 0.9300 . ? C18 C17 1.374(3) . ? N10 C50 1.136(3) . ? C16 H16 0.9300 . ? C16 C17 1.385(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.481(3) . ? C22 H22 0.9300 . ? C22 C23 1.298(3) . ? C26 C49 1.492(3) . ? C17 H17 0.9300 . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C46 C47 1.479(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.517(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C9 H9 0.9300 . ? C9 C8 1.482(4) . ? C34 H34 0.9300 . ? C34 C33 1.499(4) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C33 1.498(4) . ? C47 H47 0.9300 . ? C47 C48 1.302(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.522(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.494(4) . ? C23 H23A 1.10(3) . ? C23 H23B 1.12(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C48 H48A 1.09(4) . ? C48 H48B 1.08(6) . ?