#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:01:40 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304783 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064312.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_7064312 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 '0.09(C26 H23 N5 O3)' _chemical_formula_sum 'C H N O' _chemical_formula_weight 43.03 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-12-02 _audit_creation_method ; Olex2 1.2-ac4 (compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492) ; _audit_update_record ; 2025-09-07 deposited with the CCDC. 2025-12-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 43 _cell_length_a 9.3410(2) _cell_length_b 12.3538(3) _cell_length_c 19.8410(5) _cell_measurement_reflns_used 6481 _cell_measurement_temperature 304.6(2) _cell_measurement_theta_max 25.9870 _cell_measurement_theta_min 2.0520 _cell_volume 2289.59(9) _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 304.6(2) _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 0.961 _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 -69.00 -36.00 0.50 5.00 -- -14.97 125.00 90.00 66 2 \w -46.00 -21.00 0.50 5.00 -- -14.97 126.00 127.00 50 3 \w -38.00 58.00 0.50 5.00 -- -14.97 30.00 90.00 192 4 \w 31.00 77.00 0.50 5.00 -- 16.22 30.00 90.00 92 5 \w -7.00 18.00 0.50 5.00 -- 16.22 30.00 90.00 50 6 \w 9.00 60.00 0.50 5.00 -- 16.22-121.00 137.00 102 7 \w -58.00 -13.00 0.50 5.00 -- -14.97 125.00 -60.00 90 8 \w -45.00 -10.00 0.50 5.00 -- -14.97 125.00 -90.00 70 9 \w 13.00 48.00 0.50 5.00 -- 16.22 -10.00-119.00 70 10 \w -49.00 -23.00 0.50 5.00 -- 16.22 -10.00-119.00 52 ; _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 -0.0084840000 _diffrn_orient_matrix_UB_12 -0.0010016000 _diffrn_orient_matrix_UB_13 0.0355049000 _diffrn_orient_matrix_UB_21 0.0055369000 _diffrn_orient_matrix_UB_22 -0.0572620000 _diffrn_orient_matrix_UB_23 -0.0003279000 _diffrn_orient_matrix_UB_31 0.0752761000 _diffrn_orient_matrix_UB_32 0.0041212000 _diffrn_orient_matrix_UB_33 0.0040547000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_unetI/netI 0.0441 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.961 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 12731 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.935 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.994 _diffrn_reflns_theta_min 1.942 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59154 _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_density_diffrn 1.342 _exptl_crystal_F_000 946 _refine_diff_density_max 0.267 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.085 _refine_ls_abs_structure_details ; Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.2(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 4665 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0599 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1106P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1617 _refine_ls_wR_factor_ref 0.1825 _reflns_Friedel_coverage 0.717 _reflns_Friedel_fraction_full 0.979 _reflns_Friedel_fraction_max 0.901 _reflns_number_gt 3521 _reflns_number_total 4665 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj03725e2.cif _cod_data_source_block extr17 _cod_database_code 7064312 _shelx_shelxl_version_number 2016/4 _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. ; _reflns_odcompleteness_completeness 99.67 _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) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Rotating group: N005(H00A,H00B) 2.b Ternary CH refined with riding coordinates: C00E(H00E), C00O(H00O) 2.c Secondary CH2 refined with riding coordinates: C00P(H00C,H00D), C00S(H00F,H00G), C00U(H00H,H00I), C00V(H00K,H00L) 2.d Aromatic/amide H refined with riding coordinates: N002(H002), C009(H009), C00J(H00J), C00M(H00M), C00Q(H00Q), C00R(H00R), C00T(H00T), C00X(H00X) 2.e Idealised Me refined as rotating group: C00W(H00N,H00P,H00S) ; _shelx_res_file ; TITL extr17_a.res in P2(1)2(1)2(1) extr17.res created by SHELXL-2016/4 at 19:29:41 on 02-Dec-2020 REM Old TITL EXTR17 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.147, Rweak 0.028, Alpha 0.001, Orientation as input REM Flack x = -0.194 ( 0.747 ) from Parsons' quotients REM Formula found by SHELXT: C27 N4 O3 CELL 0.71073 9.341 12.3538 19.841 90 90 90 ZERR 43 0.0002 0.0003 0.0005 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H N O UNIT 43 43 43 43 L.S. 4 0 0 PLAN 20 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.110600 FVAR 1.02628 O001 4 0.434256 0.274956 0.699272 11.00000 0.05367 0.05990 = 0.05700 0.01215 -0.00715 0.01260 N002 3 0.247199 0.601354 0.709475 11.00000 0.03415 0.05537 = 0.03462 -0.01198 -0.00668 0.01370 AFIX 43 H002 2 0.197576 0.610263 0.673390 11.00000 -1.20000 AFIX 0 N003 3 0.193716 0.315138 0.696131 11.00000 0.04501 0.04733 = 0.04074 0.00562 -0.00022 0.00327 N004 3 0.546850 0.511472 0.804741 11.00000 0.05755 0.06890 = 0.05320 0.00126 -0.01190 -0.00459 N005 3 0.383876 0.265935 0.538768 11.00000 0.06706 0.04340 = 0.04876 -0.00526 -0.00043 0.00135 AFIX 7 H00A 2 0.447282 0.245741 0.509600 11.00000 -1.20000 H00B 2 0.389388 0.222753 0.573016 11.00000 -1.20000 AFIX 0 O006 4 0.640240 0.482097 0.766023 11.00000 0.06726 0.14268 = 0.07299 -0.01819 -0.01491 0.03089 C007 1 0.413183 0.368934 0.556572 11.00000 0.04113 0.03884 = 0.03828 -0.00293 -0.00549 0.00232 C008 1 0.498688 0.436025 0.519870 11.00000 0.04403 0.04414 = 0.03775 -0.00193 0.00057 0.00471 C009 1 0.209148 0.639319 0.773618 11.00000 0.03908 0.06209 = 0.04552 -0.02182 0.01144 0.00655 AFIX 43 H009 2 0.127058 0.678049 0.784658 11.00000 -1.20000 AFIX 0 C00A 1 0.331566 0.323625 0.676006 11.00000 0.04920 0.04070 = 0.03775 0.00101 -0.00430 0.00599 N00B 3 0.620046 0.355728 0.414262 11.00000 0.07951 0.07430 = 0.05688 -0.01023 0.01170 0.01017 C00C 1 0.103626 0.376375 0.654618 11.00000 0.04168 0.04420 = 0.04228 0.00027 -0.00380 0.00146 O00D 4 0.560353 0.509074 0.865932 11.00000 0.09796 0.14223 = 0.05069 0.02071 -0.01851 -0.00626 C00E 1 0.453839 0.595939 0.596574 11.00000 0.04456 0.03809 = 0.04297 -0.00158 -0.00385 -0.00088 AFIX 13 H00E 2 0.359486 0.621395 0.581903 11.00000 -1.20000 AFIX 0 C00F 1 0.340946 0.409368 0.619827 11.00000 0.03862 0.03734 = 0.03828 0.00100 -0.00183 0.00116 C00G 1 0.182747 0.432928 0.607158 11.00000 0.03685 0.03649 = 0.04347 -0.00248 -0.00360 0.00241 C00H 1 0.565499 0.392760 0.460426 11.00000 0.04677 0.05351 = 0.04956 -0.00126 -0.00231 0.00487 C00I 1 0.372514 0.549139 0.712967 11.00000 0.04509 0.04189 = 0.04475 -0.00508 -0.00233 -0.00323 C00J 1 0.622596 0.608322 0.500081 11.00000 0.05146 0.05654 = 0.05456 0.00376 0.00719 0.00252 AFIX 43 H00J 2 0.666079 0.575773 0.463104 11.00000 -1.20000 AFIX 0 C00K 1 0.529907 0.549522 0.536482 11.00000 0.04079 0.04087 = 0.04237 0.00084 -0.00395 0.00401 C00L 1 0.416556 0.552993 0.778153 11.00000 0.04457 0.05083 = 0.04161 -0.00229 -0.00273 -0.00865 C00M 1 0.116281 0.492133 0.557369 11.00000 0.04915 0.04604 = 0.04781 0.01046 -0.00672 0.00391 AFIX 43 H00M 2 0.169459 0.528576 0.524882 11.00000 -1.20000 AFIX 0 C00N 1 0.309103 0.610478 0.814202 11.00000 0.05883 0.05891 = 0.04669 -0.01078 0.01265 -0.01353 C00O 1 0.431565 0.505464 0.649371 11.00000 0.03770 0.04173 = 0.03861 -0.00610 -0.00171 0.00114 AFIX 13 H00O 2 0.526500 0.476273 0.659937 11.00000 -1.20000 AFIX 0 C00P 1 0.535746 0.691983 0.624956 11.00000 0.06832 0.04370 = 0.05877 -0.00801 -0.00257 -0.00977 AFIX 23 H00C 2 0.625086 0.667343 0.644594 11.00000 -1.20000 H00D 2 0.479769 0.726346 0.660139 11.00000 -1.20000 AFIX 0 C00Q 1 -0.033487 0.495982 0.556975 11.00000 0.05365 0.05794 = 0.07107 0.00876 -0.01675 0.00987 AFIX 43 H00Q 2 -0.081068 0.535073 0.523767 11.00000 -1.20000 AFIX 0 C00R 1 -0.043807 0.380857 0.655586 11.00000 0.04292 0.06370 = 0.06093 0.00994 0.00234 0.00335 AFIX 43 H00R 2 -0.096904 0.344612 0.688187 11.00000 -1.20000 AFIX 0 C00S 1 0.566585 0.773467 0.568952 11.00000 0.06551 0.03937 = 0.07534 0.00263 -0.00449 -0.00814 AFIX 23 H00F 2 0.477184 0.797053 0.548879 11.00000 -1.20000 H00G 2 0.614017 0.836425 0.587788 11.00000 -1.20000 AFIX 0 C00T 1 -0.109833 0.442429 0.605276 11.00000 0.03544 0.07123 = 0.08839 0.01106 -0.00314 0.00837 AFIX 43 H00T 2 -0.209197 0.447067 0.604691 11.00000 -1.20000 AFIX 0 C00U 1 0.143641 0.234392 0.744220 11.00000 0.05609 0.06771 = 0.05242 0.01461 0.00273 -0.00482 AFIX 23 H00H 2 0.221412 0.184418 0.753240 11.00000 -1.20000 H00I 2 0.066849 0.193422 0.723428 11.00000 -1.20000 AFIX 0 C00V 1 0.659950 0.723631 0.515727 11.00000 0.07771 0.05347 = 0.07280 0.00446 0.01064 -0.01383 AFIX 23 H00K 2 0.652072 0.766117 0.474782 11.00000 -1.20000 H00L 2 0.758817 0.726829 0.530547 11.00000 -1.20000 AFIX 0 C00W 1 0.300598 0.638718 0.887282 11.00000 0.07958 0.11992 = 0.05231 -0.02473 0.01756 -0.01397 AFIX 137 H00N 2 0.380601 0.683557 0.899240 11.00000 -1.50000 H00P 2 0.302584 0.573629 0.913696 11.00000 -1.50000 H00S 2 0.213141 0.677122 0.895884 11.00000 -1.50000 AFIX 0 C00X 1 0.091256 0.277881 0.809512 11.00000 0.09861 0.15086 = 0.04973 0.01881 0.01040 0.00664 AFIX 43 H00X 2 0.061762 0.226116 0.840582 11.00000 -1.20000 AFIX 0 C00Y 1 0.081082 0.373371 0.828687 11.00000 0.17386 0.14096 = 0.11410 -0.04920 0.01388 0.00694 HKLF 4 REM extr17_a.res in P2(1)2(1)2(1) REM R1 = 0.0599 for 3521 Fo > 4sig(Fo) and 0.0794 for all 4665 data REM 309 parameters refined using 0 restraints END WGHT 0.1103 0.0000 REM Highest difference peak 0.267, deepest hole -0.428, 1-sigma level 0.085 Q1 1 -0.0010 0.3723 0.8783 11.00000 0.05 0.27 Q2 1 0.0235 0.2813 0.8626 11.00000 0.05 0.25 Q3 1 0.0678 0.4182 0.8946 11.00000 0.05 0.25 Q4 1 0.2964 0.2222 0.5480 11.00000 0.05 0.23 Q5 1 0.0926 0.4586 0.9190 11.00000 0.05 0.23 Q6 1 0.4187 0.5399 0.9437 11.00000 0.05 0.21 Q7 1 0.5431 0.1404 0.5198 11.00000 0.05 0.20 Q8 1 0.0914 0.4612 0.8638 11.00000 0.05 0.20 Q9 1 0.5602 0.9390 0.5801 11.00000 0.05 0.20 Q10 1 0.3921 0.5768 0.9822 11.00000 0.05 0.20 Q11 1 -0.0070 0.4752 0.4762 11.00000 0.05 0.20 Q12 1 0.3709 0.2581 0.4785 11.00000 0.05 0.20 Q13 1 0.7394 0.4161 0.4558 11.00000 0.05 0.20 Q14 1 -0.0365 0.3223 0.8431 11.00000 0.05 0.20 Q15 1 0.2743 0.5332 0.4777 11.00000 0.05 0.20 Q16 1 0.5590 0.4612 0.9424 11.00000 0.05 0.19 Q17 1 0.2821 0.4450 0.8963 11.00000 0.05 0.19 Q18 1 0.5049 0.1172 0.5240 11.00000 0.05 0.19 Q19 1 0.6073 0.2159 0.5073 11.00000 0.05 0.19 Q20 1 0.3183 0.8230 0.5403 11.00000 0.05 0.19 ; _shelx_res_checksum 68009 _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 1.394 _oxdiff_exptl_absorpt_empirical_full_min 0.699 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 O001 O 0.4343(3) 0.2750(3) 0.69927(16) 0.0569(8) Uani 1 1 d . . . . . N002 N 0.2472(3) 0.6014(3) 0.70948(15) 0.0414(8) Uani 1 1 d . . . . . H002 H 0.197576 0.610263 0.673390 0.050 Uiso 1 1 calc R . . . . N003 N 0.1937(4) 0.3151(3) 0.69613(17) 0.0444(8) Uani 1 1 d . . . . . N004 N 0.5469(5) 0.5115(4) 0.8047(2) 0.0599(10) Uani 1 1 d . . . . . N005 N 0.3839(4) 0.2659(3) 0.53877(19) 0.0531(9) Uani 1 1 d . . . . . H00A H 0.447282 0.245741 0.509600 0.064 Uiso 1 1 d GR . . . . H00B H 0.389388 0.222753 0.573016 0.064 Uiso 1 1 d GR . . . . O006 O 0.6402(4) 0.4821(5) 0.7660(2) 0.0943(14) Uani 1 1 d . . . . . C007 C 0.4132(4) 0.3689(3) 0.55657(19) 0.0394(9) Uani 1 1 d . . . . . C008 C 0.4987(4) 0.4360(3) 0.5199(2) 0.0420(9) Uani 1 1 d . . . . . C009 C 0.2091(4) 0.6393(4) 0.7736(2) 0.0489(10) Uani 1 1 d . . . . . H009 H 0.127058 0.678049 0.784658 0.059 Uiso 1 1 calc R . . . . C00A C 0.3316(4) 0.3236(3) 0.67601(19) 0.0425(9) Uani 1 1 d . . . . . N00B N 0.6200(5) 0.3557(4) 0.4143(2) 0.0702(12) Uani 1 1 d . . . . . C00C C 0.1036(4) 0.3764(3) 0.6546(2) 0.0427(9) Uani 1 1 d . . . . . O00D O 0.5604(5) 0.5091(4) 0.86593(17) 0.0970(14) Uani 1 1 d . . . . . C00E C 0.4538(4) 0.5959(3) 0.59657(19) 0.0419(9) Uani 1 1 d . . . . . H00E H 0.359486 0.621395 0.581903 0.050 Uiso 1 1 calc R . . . . C00F C 0.3409(4) 0.4094(3) 0.61983(19) 0.0381(9) Uani 1 1 d . . . . . C00G C 0.1827(4) 0.4329(3) 0.6072(2) 0.0389(9) Uani 1 1 d . . . . . C00H C 0.5655(5) 0.3928(4) 0.4604(2) 0.0499(10) Uani 1 1 d . . . . . C00I C 0.3725(5) 0.5491(3) 0.7130(2) 0.0439(10) Uani 1 1 d . . . . . C00J C 0.6226(5) 0.6083(4) 0.5001(2) 0.0542(11) Uani 1 1 d . . . . . H00J H 0.666079 0.575773 0.463104 0.065 Uiso 1 1 calc R . . . . C00K C 0.5299(4) 0.5495(3) 0.5365(2) 0.0413(9) Uani 1 1 d . . . . . C00L C 0.4166(4) 0.5530(3) 0.7782(2) 0.0457(10) Uani 1 1 d . . . . . C00M C 0.1163(5) 0.4921(4) 0.5574(2) 0.0477(10) Uani 1 1 d . . . . . H00M H 0.169459 0.528576 0.524882 0.057 Uiso 1 1 calc R . . . . C00N C 0.3091(5) 0.6105(4) 0.8142(2) 0.0548(11) Uani 1 1 d . . . . . C00O C 0.4316(4) 0.5055(3) 0.64937(18) 0.0393(8) Uani 1 1 d . . . . . H00O H 0.526500 0.476273 0.659937 0.047 Uiso 1 1 calc R . . . . C00P C 0.5357(6) 0.6920(4) 0.6250(2) 0.0569(12) Uani 1 1 d . . . . . H00C H 0.625086 0.667343 0.644594 0.068 Uiso 1 1 calc R . . . . H00D H 0.479769 0.726346 0.660139 0.068 Uiso 1 1 calc R . . . . C00Q C -0.0335(5) 0.4960(4) 0.5570(3) 0.0609(12) Uani 1 1 d . . . . . H00Q H -0.081068 0.535073 0.523767 0.073 Uiso 1 1 calc R . . . . C00R C -0.0438(5) 0.3809(4) 0.6556(2) 0.0559(11) Uani 1 1 d . . . . . H00R H -0.096904 0.344612 0.688187 0.067 Uiso 1 1 calc R . . . . C00S C 0.5666(6) 0.7735(4) 0.5690(3) 0.0601(12) Uani 1 1 d . . . . . H00F H 0.477184 0.797053 0.548879 0.072 Uiso 1 1 calc R . . . . H00G H 0.614017 0.836425 0.587788 0.072 Uiso 1 1 calc R . . . . C00T C -0.1098(5) 0.4424(4) 0.6053(3) 0.0650(14) Uani 1 1 d . . . . . H00T H -0.209197 0.447067 0.604691 0.078 Uiso 1 1 calc R . . . . C00U C 0.1436(5) 0.2344(4) 0.7442(2) 0.0587(12) Uani 1 1 d . . . . . H00H H 0.221412 0.184418 0.753240 0.070 Uiso 1 1 calc R . . . . H00I H 0.066849 0.193422 0.723428 0.070 Uiso 1 1 calc R . . . . C00V C 0.6600(6) 0.7236(4) 0.5157(3) 0.0680(14) Uani 1 1 d . . . . . H00K H 0.652072 0.766117 0.474782 0.082 Uiso 1 1 calc R . . . . H00L H 0.758817 0.726829 0.530547 0.082 Uiso 1 1 calc R . . . . C00W C 0.3006(6) 0.6387(6) 0.8873(2) 0.0839(18) Uani 1 1 d . . . . . H00N H 0.380601 0.683557 0.899240 0.126 Uiso 1 1 calc GR . . . . H00P H 0.302584 0.573629 0.913696 0.126 Uiso 1 1 calc GR . . . . H00S H 0.213141 0.677122 0.895884 0.126 Uiso 1 1 calc GR . . . . C00X C 0.0913(7) 0.2779(7) 0.8095(3) 0.100(2) Uani 1 1 d . . . . . H00X H 0.061762 0.226116 0.840582 0.120 Uiso 1 1 calc R . . . . C00Y C 0.0811(13) 0.3734(9) 0.8287(5) 0.143(4) Uani 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 O001 0.0537(19) 0.0599(18) 0.0570(18) 0.0122(15) -0.0072(15) 0.0126(16) N002 0.0342(16) 0.0554(19) 0.0346(16) -0.0120(15) -0.0067(13) 0.0137(15) N003 0.0450(19) 0.0473(18) 0.0407(18) 0.0056(15) -0.0002(14) 0.0033(16) N004 0.058(2) 0.069(2) 0.053(2) 0.001(2) -0.0119(19) -0.005(2) N005 0.067(2) 0.0434(19) 0.049(2) -0.0053(17) -0.0004(18) 0.0013(18) O006 0.067(2) 0.143(4) 0.073(2) -0.018(3) -0.015(2) 0.031(3) C007 0.041(2) 0.0388(19) 0.0383(19) -0.0029(17) -0.0055(16) 0.0023(18) C008 0.044(2) 0.044(2) 0.038(2) -0.0019(17) 0.0006(16) 0.0047(18) C009 0.039(2) 0.062(3) 0.046(2) -0.022(2) 0.0114(18) 0.007(2) C00A 0.049(2) 0.041(2) 0.038(2) 0.0010(17) -0.0043(17) 0.0060(19) N00B 0.080(3) 0.074(3) 0.057(2) -0.010(2) 0.012(2) 0.010(2) C00C 0.042(2) 0.044(2) 0.042(2) 0.0003(18) -0.0038(17) 0.0015(18) O00D 0.098(3) 0.142(4) 0.051(2) 0.021(3) -0.019(2) -0.006(3) C00E 0.045(2) 0.0381(19) 0.043(2) -0.0016(17) -0.0039(17) -0.0009(19) C00F 0.039(2) 0.0373(19) 0.0383(19) 0.0010(17) -0.0018(16) 0.0012(16) C00G 0.037(2) 0.0365(19) 0.043(2) -0.0025(16) -0.0036(16) 0.0024(16) C00H 0.047(2) 0.054(2) 0.050(2) -0.001(2) -0.002(2) 0.005(2) C00I 0.045(2) 0.042(2) 0.045(2) -0.0051(18) -0.0023(18) -0.0032(18) C00J 0.051(2) 0.057(3) 0.055(3) 0.004(2) 0.007(2) 0.003(2) C00K 0.041(2) 0.041(2) 0.042(2) 0.0008(17) -0.0040(17) 0.0040(17) C00L 0.045(2) 0.051(2) 0.042(2) -0.0023(18) -0.0027(18) -0.009(2) C00M 0.049(2) 0.046(2) 0.048(2) 0.010(2) -0.0067(18) 0.0039(19) C00N 0.059(3) 0.059(3) 0.047(2) -0.011(2) 0.013(2) -0.014(2) C00O 0.038(2) 0.0417(19) 0.0386(19) -0.0061(18) -0.0017(16) 0.0011(18) C00P 0.068(3) 0.044(2) 0.059(3) -0.008(2) -0.003(2) -0.010(2) C00Q 0.054(3) 0.058(3) 0.071(3) 0.009(3) -0.017(2) 0.010(2) C00R 0.043(2) 0.064(3) 0.061(3) 0.010(2) 0.002(2) 0.003(2) C00S 0.066(3) 0.039(2) 0.075(3) 0.003(2) -0.004(3) -0.008(2) C00T 0.035(2) 0.071(3) 0.088(4) 0.011(3) -0.003(2) 0.008(2) C00U 0.056(3) 0.068(3) 0.052(3) 0.015(2) 0.003(2) -0.005(2) C00V 0.078(4) 0.053(3) 0.073(3) 0.004(3) 0.011(3) -0.014(3) C00W 0.080(4) 0.120(5) 0.052(3) -0.025(3) 0.018(3) -0.014(4) C00X 0.099(5) 0.151(7) 0.050(3) 0.019(4) 0.010(3) 0.007(5) C00Y 0.174(9) 0.141(8) 0.114(6) -0.049(6) 0.014(6) 0.007(7) 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 C009 N002 H002 125.2 . . ? C00I N002 H002 125.2 . . ? C00I N002 C009 109.6(3) . . ? C00A N003 C00C 110.9(3) . . ? C00A N003 C00U 123.5(3) . . ? C00C N003 C00U 124.2(4) . . ? O006 N004 O00D 123.1(5) . . ? O006 N004 C00L 119.1(4) . . ? O00D N004 C00L 117.8(4) . . ? H00A N005 H00B 107.9 . . ? C007 N005 H00A 108.0 . . ? C007 N005 H00B 111.3 . . ? N005 C007 C008 123.6(4) . . ? N005 C007 C00F 116.0(4) . . ? C008 C007 C00F 120.3(3) . . ? C007 C008 C00H 117.8(4) . . ? C007 C008 C00K 125.2(4) . . ? C00H C008 C00K 116.9(4) . . ? N002 C009 H009 126.5 . . ? C00N C009 N002 107.0(4) . . ? C00N C009 H009 126.5 . . ? O001 C00A N003 126.7(4) . . ? O001 C00A C00F 124.5(4) . . ? N003 C00A C00F 108.7(3) . . ? C00G C00C N003 110.6(3) . . ? C00R C00C N003 127.9(4) . . ? C00R C00C C00G 121.5(4) . . ? C00K C00E H00E 108.2 . . ? C00K C00E C00O 109.0(3) . . ? C00K C00E C00P 110.7(4) . . ? C00O C00E H00E 108.2 . . ? C00P C00E H00E 108.2 . . ? C00P C00E C00O 112.4(3) . . ? C007 C00F C00A 113.5(3) . . ? C007 C00F C00G 111.0(3) . . ? C007 C00F C00O 108.6(3) . . ? C00A C00F C00O 106.3(3) . . ? C00G C00F C00A 101.3(3) . . ? C00G C00F C00O 116.0(3) . . ? C00C C00G C00F 107.9(3) . . ? C00M C00G C00C 121.0(4) . . ? C00M C00G C00F 131.0(4) . . ? N00B C00H C008 177.9(5) . . ? N002 C00I C00L 107.3(4) . . ? N002 C00I C00O 117.2(3) . . ? C00L C00I C00O 135.4(4) . . ? C00K C00J H00J 118.2 . . ? C00K C00J C00V 123.6(4) . . ? C00V C00J H00J 118.2 . . ? C008 C00K C00E 116.6(3) . . ? C00J C00K C008 121.6(4) . . ? C00J C00K C00E 121.7(4) . . ? N004 C00L C00N 126.7(4) . . ? C00I C00L N004 126.9(4) . . ? C00I C00L C00N 106.4(4) . . ? C00G C00M H00M 120.9 . . ? C00G C00M C00Q 118.2(4) . . ? C00Q C00M H00M 120.9 . . ? C009 C00N C00L 109.7(4) . . ? C009 C00N C00W 120.4(5) . . ? C00L C00N C00W 130.0(5) . . ? C00E C00O C00F 111.5(3) . . ? C00E C00O H00O 106.8 . . ? C00F C00O H00O 106.8 . . ? C00I C00O C00E 111.4(3) . . ? C00I C00O C00F 113.1(3) . . ? C00I C00O H00O 106.8 . . ? C00E C00P H00C 109.7 . . ? C00E C00P H00D 109.7 . . ? C00E C00P C00S 109.9(4) . . ? H00C C00P H00D 108.2 . . ? C00S C00P H00C 109.7 . . ? C00S C00P H00D 109.7 . . ? C00M C00Q H00Q 119.9 . . ? C00T C00Q C00M 120.1(4) . . ? C00T C00Q H00Q 119.9 . . ? C00C C00R H00R 121.5 . . ? C00C C00R C00T 116.9(4) . . ? C00T C00R H00R 121.5 . . ? C00P C00S H00F 109.5 . . ? C00P C00S H00G 109.5 . . ? H00F C00S H00G 108.1 . . ? C00V C00S C00P 110.6(4) . . ? C00V C00S H00F 109.5 . . ? C00V C00S H00G 109.5 . . ? C00Q C00T C00R 122.3(4) . . ? C00Q C00T H00T 118.9 . . ? C00R C00T H00T 118.9 . . ? N003 C00U H00H 108.4 . . ? N003 C00U H00I 108.4 . . ? N003 C00U C00X 115.4(5) . . ? H00H C00U H00I 107.5 . . ? C00X C00U H00H 108.4 . . ? C00X C00U H00I 108.4 . . ? C00J C00V C00S 113.6(4) . . ? C00J C00V H00K 108.8 . . ? C00J C00V H00L 108.8 . . ? C00S C00V H00K 108.8 . . ? C00S C00V H00L 108.8 . . ? H00K C00V H00L 107.7 . . ? C00N C00W H00N 109.5 . . ? C00N C00W H00P 109.5 . . ? C00N C00W H00S 109.5 . . ? H00N C00W H00P 109.5 . . ? H00N C00W H00S 109.5 . . ? H00P C00W H00S 109.5 . . ? C00U C00X H00X 115.3 . . ? C00Y C00X C00U 129.4(8) . . ? C00Y C00X H00X 115.3 . . ? 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 O001 C00A 1.223(5) . ? N002 H002 0.8600 . ? N002 C009 1.402(5) . ? N002 C00I 1.338(5) . ? N003 C00A 1.352(5) . ? N003 C00C 1.400(5) . ? N003 C00U 1.457(6) . ? N004 O006 1.218(5) . ? N004 O00D 1.221(5) . ? N004 C00L 1.422(6) . ? N005 H00A 0.8648 . ? N005 H00B 0.8654 . ? N005 C007 1.349(5) . ? C007 C008 1.362(5) . ? C007 C00F 1.510(5) . ? C008 C00H 1.437(6) . ? C008 C00K 1.470(5) . ? C009 H009 0.9300 . ? C009 C00N 1.283(6) . ? C00A C00F 1.540(5) . ? N00B C00H 1.144(6) . ? C00C C00G 1.386(6) . ? C00C C00R 1.378(6) . ? C00E H00E 0.9800 . ? C00E C00K 1.502(6) . ? C00E C00O 1.546(5) . ? C00E C00P 1.520(6) . ? C00F C00G 1.527(6) . ? C00F C00O 1.571(5) . ? C00G C00M 1.377(5) . ? C00I C00L 1.358(6) . ? C00I C00O 1.479(5) . ? C00J H00J 0.9300 . ? C00J C00K 1.341(6) . ? C00J C00V 1.499(7) . ? C00L C00N 1.422(6) . ? C00M H00M 0.9300 . ? C00M C00Q 1.400(6) . ? C00N C00W 1.493(6) . ? C00O H00O 0.9800 . ? C00P H00C 0.9700 . ? C00P H00D 0.9700 . ? C00P C00S 1.527(6) . ? C00Q H00Q 0.9300 . ? C00Q C00T 1.366(7) . ? C00R H00R 0.9300 . ? C00R C00T 1.398(7) . ? C00S H00F 0.9700 . ? C00S H00G 0.9700 . ? C00S C00V 1.502(7) . ? C00T H00T 0.9300 . ? C00U H00H 0.9700 . ? C00U H00I 0.9700 . ? C00U C00X 1.485(8) . ? C00V H00K 0.9700 . ? C00V H00L 0.9700 . ? C00W H00N 0.9600 . ? C00W H00P 0.9600 . ? C00W H00S 0.9600 . ? C00X H00X 0.9300 . ? C00X C00Y 1.243(10) . ?