#------------------------------------------------------------------------------ #$Date: 2014-04-23 10:47:40 +0100 (Wed, 23 Apr 2014) $ #$Revision: 111483 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/26/7112613.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_7112613 loop_ _publ_author_name 'Lena Hahn' 'Simin Oz' 'Hubert Wadepohl' 'Lutz H. Gade' _publ_section_title ; Highly emissive water-soluble tetraazaperopyrenes as fluorescent markers ; _journal_name_full Chem.Commun. _journal_page_first 4941 _journal_paper_doi 10.1039/C4CC01254B _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C48 H20 F14 N8, 3(C4 H8 O)' _chemical_formula_sum 'C60 H44 F14 N8 O3' _chemical_formula_weight 1191.03 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_code ga_lh5 _audit_creation_date 2014-02-12 _audit_update_record 'Wed Feb 12 16:11:49 CET 2014' _cell_angle_alpha 90 _cell_angle_beta 108.873(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 21.096(10) _cell_length_b 11.551(5) _cell_length_c 22.445(10) _cell_measurement_reflns_used 8099 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.47 _cell_measurement_theta_min 2.39 _cell_volume 5175(4) _computing_cell_refinement ; SAINT 8.x (Bruker AXS, 1997-2012). Includes estimated systematic errors of the unit cell constants from Monte Carlo simulations. ; _computing_data_collection 'SMART-5.631 (Bruker AXS, 2003)' _computing_data_reduction 'SAINT 8.x (Bruker AXS, 1997-2011)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SIR2004 (Giacovazzo et al., 2004)' _diffrn_ambient_environment 'perfluoro polyether oil' _diffrn_ambient_temperature 100(1) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.19 _diffrn_detector_type CCD-PXL-KAF2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker AXS Smart 1000' _diffrn_measurement_method '\f- and \w-scans' _diffrn_measurement_specimen_support 'polyimid foil' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_unetI/netI 0.0389 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 61657 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.659 _diffrn_reflns_theta_min 1.918 _diffrn_source 'sealed X-Ray tube (Mo)' _diffrn_source_type 'fine focus tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_T_max 0.8622 _exptl_absorpt_correction_T_min 0.7876 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements (Blessing 1995) SADABS (Sheldrick & Bruker AXS, 2004-2008) ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.529 _exptl_crystal_description plate _exptl_crystal_F_000 2440 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.813 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 390 _refine_ls_number_reflns 7908 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0554 _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^)+(0.0660P)^2^+8.4620P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1328 _refine_ls_wR_factor_ref 0.1454 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5881 _reflns_number_total 7908 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL ga_lh5 - #1860 - in C2/c - sir2004 - smart CELL 0.71073 21.09641 11.55145 22.44485 90 108.8731 90 ZERR 4 0.00971 0.00526 0.01035 0 0.011 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H F N O UNIT 240 176 56 32 12 L.S. 10 PLAN 30 SIZE 0.18 0.17 0.06 TEMP -173 BOND $H CONF fmap 2 acta REM /struk/ga/ga_lh5/65s/ga_lh5.hkl WGHT 0.066000 8.462000 FVAR 0.05806 F1 3 0.037255 -0.052552 0.193068 11.00000 0.02761 0.02100 = 0.02147 0.00668 0.01651 0.00673 F2 3 0.083132 0.114124 0.186399 11.00000 0.01637 0.02516 = 0.02670 -0.01448 0.00975 -0.00603 F3 3 -0.053756 -0.017978 0.074817 11.00000 0.01602 0.03645 = 0.02728 -0.01641 0.00465 -0.00198 F4 3 -0.007353 0.149465 0.070482 11.00000 0.03322 0.03150 = 0.02598 0.01342 0.01843 0.01356 F5 3 -0.080744 0.051106 0.180462 11.00000 0.02737 0.02626 = 0.03966 0.00142 0.02559 0.00033 F6 3 -0.033664 0.215015 0.178982 11.00000 0.02958 0.02179 = 0.04758 -0.01332 0.02273 -0.00170 F7 3 -0.119414 0.164609 0.101481 11.00000 0.02725 0.07350 = 0.02582 0.00307 0.00554 0.03171 N1 4 0.076755 -0.144463 0.102123 11.00000 0.01130 0.01310 = 0.01663 -0.00157 0.00700 0.00030 N2 4 0.136309 0.033825 0.103861 11.00000 0.01163 0.01280 = 0.01559 -0.00144 0.00647 0.00023 N3 4 0.204379 0.362781 0.092901 11.00000 0.02286 0.01130 = 0.03167 0.00047 0.01339 0.00289 N501 4 0.560753 -0.083609 -0.070336 11.00000 0.01368 0.02280 = 0.02871 -0.00551 0.01140 -0.00452 C1 1 0.115228 -0.197800 0.072623 11.00000 0.00964 0.01259 = 0.01332 -0.00078 0.00466 0.00024 C2 1 0.394498 -0.180414 -0.057760 11.00000 0.00953 0.01273 = 0.01412 -0.00021 0.00521 -0.00175 C3 1 0.352465 -0.126688 -0.031097 11.00000 0.01039 0.01140 = 0.01624 -0.00132 0.00609 -0.00199 H3 2 0.359225 -0.043687 -0.023205 11.00000 -1.20000 C4 1 0.300616 -0.186077 -0.015218 11.00000 0.00946 0.01130 = 0.01303 -0.00164 0.00479 -0.00198 C5 1 0.209009 -0.194438 0.029340 11.00000 0.00954 0.00990 = 0.01285 -0.00136 0.00441 -0.00097 C6 1 0.166901 -0.137197 0.058250 11.00000 0.00878 0.01147 = 0.01352 -0.00094 0.00506 -0.00016 C7 1 0.175074 -0.018235 0.074256 11.00000 0.01073 0.01103 = 0.01253 -0.00042 0.00413 -0.00057 C8 1 0.227472 0.046941 0.060687 11.00000 0.01076 0.01087 = 0.01430 -0.00053 0.00485 -0.00083 C9 1 0.266862 -0.009333 0.031791 11.00000 0.01187 0.01037 = 0.01555 -0.00120 0.00634 -0.00180 H9 2 0.300713 0.033184 0.022065 11.00000 -1.20000 C10 1 0.259430 -0.129593 0.014858 11.00000 0.01023 0.01024 = 0.01329 -0.00156 0.00525 -0.00111 C21 1 0.091283 -0.033926 0.116334 11.00000 0.01085 0.01434 = 0.01468 -0.00083 0.00604 0.00098 C23 1 0.049760 0.023533 0.152547 11.00000 0.01483 0.01169 = 0.01524 -0.00186 0.00781 -0.00149 C24 1 -0.018275 0.069738 0.109954 11.00000 0.01552 0.01842 = 0.01540 -0.00020 0.00714 0.00168 C25 1 -0.063633 0.126478 0.143908 11.00000 0.01401 0.02133 = 0.02059 0.00017 0.00714 0.00429 C26 1 0.446496 -0.110949 -0.072867 11.00000 0.01126 0.01368 = 0.01598 -0.00347 0.00788 -0.00236 C27 1 0.512749 -0.147680 -0.059175 11.00000 0.01165 0.01740 = 0.02283 -0.00191 0.00752 -0.00073 AFIX 43 H27 2 0.524475 -0.222126 -0.040956 11.00000 -1.20000 AFIX 0 C28 1 0.542969 0.020335 -0.097109 11.00000 0.01691 0.02253 = 0.02364 -0.00565 0.01171 -0.00900 AFIX 43 H28 2 0.576226 0.065817 -0.106198 11.00000 -1.20000 AFIX 0 C29 1 0.478926 0.064951 -0.112208 11.00000 0.02088 0.01704 = 0.02689 -0.00030 0.01191 -0.00504 AFIX 43 H29 2 0.468646 0.139334 -0.130902 11.00000 -1.20000 AFIX 0 C30 1 0.429926 -0.001352 -0.099451 11.00000 0.01465 0.01563 = 0.02239 0.00067 0.00850 -0.00108 AFIX 43 H30 2 0.385632 0.027596 -0.108722 11.00000 -1.20000 AFIX 0 C31 1 0.241630 0.170077 0.079131 11.00000 0.01441 0.01043 = 0.01593 -0.00025 0.00747 -0.00017 C32 1 0.191766 0.251917 0.075866 11.00000 0.01539 0.01377 = 0.02302 0.00141 0.00837 0.00119 AFIX 43 H32 2 0.146361 0.227425 0.060696 11.00000 -1.20000 AFIX 0 C33 1 0.268358 0.397005 0.113860 11.00000 0.02648 0.01183 = 0.02849 -0.00277 0.01343 -0.00229 AFIX 43 H33 2 0.277825 0.475013 0.127166 11.00000 -1.20000 AFIX 0 C34 1 0.321230 0.324359 0.117060 11.00000 0.01827 0.01556 = 0.03107 -0.00460 0.00975 -0.00595 AFIX 43 H34 2 0.365951 0.352479 0.130900 11.00000 -1.20000 AFIX 0 C35 1 0.307817 0.209430 0.099669 11.00000 0.01464 0.01333 = 0.02676 -0.00302 0.00931 -0.00063 AFIX 43 H35 2 0.343466 0.157698 0.101712 11.00000 -1.20000 AFIX 0 O41 5 0.211057 -0.126536 0.220755 11.00000 0.02361 0.02536 = 0.03291 0.00195 0.00807 0.00279 C41 1 0.218242 -0.248602 0.231695 11.00000 0.03460 0.02623 = 0.02563 0.00373 0.00867 -0.00143 AFIX 23 H41A 2 0.175583 -0.289123 0.210292 11.00000 -1.20000 H41B 2 0.231898 -0.265708 0.277326 11.00000 -1.20000 AFIX 0 C42 1 0.272480 -0.286096 0.204439 11.00000 0.02966 0.02597 = 0.03047 0.00061 0.00435 0.00535 AFIX 23 H42A 2 0.252516 -0.312719 0.160388 11.00000 -1.20000 H42B 2 0.300018 -0.349340 0.229729 11.00000 -1.20000 AFIX 0 C43 1 0.314695 -0.176521 0.207740 11.00000 0.02935 0.03639 = 0.05173 -0.00291 0.01396 0.00048 AFIX 23 H43A 2 0.360897 -0.187465 0.236795 11.00000 -1.20000 H43B 2 0.316575 -0.155432 0.165593 11.00000 -1.20000 AFIX 0 C44 1 0.277635 -0.083784 0.232611 11.00000 0.02678 0.02792 = 0.02655 -0.00272 0.00360 -0.00188 AFIX 23 H44A 2 0.299887 -0.071446 0.278281 11.00000 -1.20000 H44B 2 0.276866 -0.009428 0.210455 11.00000 -1.20000 AFIX 0 O51 5 0.500000 -0.000296 -0.250000 10.50000 0.05359 0.03015 = 0.03628 0.00000 0.02157 0.00000 C51 1 0.442001 -0.072364 -0.261097 11.00000 0.04272 0.04401 = 0.02941 0.00276 0.01462 0.00254 AFIX 23 H51A 2 0.407130 -0.050063 -0.300887 11.00000 -1.20000 H51B 2 0.423183 -0.064740 -0.226198 11.00000 -1.20000 AFIX 0 PART 2 C52 1 0.464937 -0.195251 -0.265139 11.00000 0.05170 0.03854 = 0.12752 0.02663 0.02022 0.00130 AFIX 23 H52A 2 0.442831 -0.249094 -0.243734 11.00000 -1.20000 H52B 2 0.454023 -0.219395 -0.309651 11.00000 -1.20000 AFIX 0 HKLF 4 REM ga_lh5 - #1860 - in C2/c - sir2004 - smart REM R1 = 0.0554 for 5881 Fo > 4sig(Fo) and 0.0798 for all 7908 data REM 390 parameters refined using 0 restraints END WGHT 0.0660 8.4778 REM Highest difference peak 0.813, deepest hole -0.778, 1-sigma level 0.069 Q1 1 0.4678 -0.1773 -0.2298 11.00000 0.05 0.81 Q2 1 0.3240 -0.1804 0.2491 11.00000 0.05 0.77 Q3 1 -0.0395 0.0976 0.1279 11.00000 0.05 0.53 Q4 1 0.1888 -0.1628 0.0443 11.00000 0.05 0.52 Q5 1 0.2357 -0.1646 0.0246 11.00000 0.05 0.51 Q6 1 0.3262 -0.1607 -0.0221 11.00000 0.05 0.51 Q7 1 0.1386 -0.1682 0.0639 11.00000 0.05 0.50 Q8 1 0.2802 -0.1588 -0.0009 11.00000 0.05 0.48 Q9 1 0.2666 -0.0741 0.0316 11.00000 0.05 0.45 Q10 1 0.2016 0.0158 0.0653 11.00000 0.05 0.43 Q11 1 0.0723 -0.0055 0.1360 11.00000 0.05 0.43 Q12 1 0.2328 0.1103 0.0686 11.00000 0.05 0.41 Q13 1 0.0146 0.0432 0.1303 11.00000 0.05 0.40 Q14 1 0.2175 0.2146 0.0778 11.00000 0.05 0.40 Q15 1 0.3734 -0.1630 -0.0446 11.00000 0.05 0.39 Q16 1 0.1711 -0.0789 0.0661 11.00000 0.05 0.39 Q17 1 0.4791 -0.1234 -0.0665 11.00000 0.05 0.39 Q18 1 0.1094 -0.2571 0.0646 11.00000 0.05 0.39 Q19 1 0.2954 0.3604 0.1244 11.00000 0.05 0.38 Q20 1 0.2503 0.0181 0.0515 11.00000 0.05 0.38 Q21 1 0.4217 -0.1456 -0.0639 11.00000 0.05 0.37 Q22 1 0.4586 0.0268 -0.1053 11.00000 0.05 0.37 Q23 1 0.0957 -0.1648 0.0875 11.00000 0.05 0.36 Q24 1 0.2953 -0.2442 -0.0221 11.00000 0.05 0.35 Q25 1 0.1109 0.0001 0.1077 11.00000 0.05 0.35 Q26 1 0.5057 -0.2078 -0.3083 11.00000 0.05 0.35 Q27 1 0.5130 0.0384 -0.0966 11.00000 0.05 0.35 Q28 1 0.4416 -0.0563 -0.0797 11.00000 0.05 0.34 Q29 1 0.4350 -0.2592 -0.2695 11.00000 0.05 0.32 Q30 1 -0.0564 0.2191 0.1398 11.00000 0.05 0.32 ; _[local]_cod_data_source_file c4cc01254b2.cif _[local]_cod_data_source_block ga_lh5 _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_original_cell_volume 5176(4) _cod_database_code 7112613 _audit_block_refno 1860 _audit_block_usercomment LH353 _shelxl_version_number 2013-4 _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 0.992 _shelx_estimated_absorpt_t_min 0.977 _diffrn_reflns_laue_measured_fraction_full 0.999 _diffrn_reflns_laue_measured_fraction_max 0.987 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.987 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C51(H51A, H51B), C52(H52A,H52B) 2.b Aromatic/amide H refined with riding coordinates: C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35) ; _shelx_res_checksum 58285 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 F1 F 0.03725(6) -0.05255(9) 0.19307(5) 0.0213(2) Uani 1 1 d . . . . . F2 F 0.08313(5) 0.11412(9) 0.18640(5) 0.0221(2) Uani 1 1 d . . . . . F3 F -0.05376(5) -0.01798(11) 0.07482(5) 0.0271(3) Uani 1 1 d . . . . . F4 F -0.00735(6) 0.14947(10) 0.07048(5) 0.0281(3) Uani 1 1 d . . . . . F5 F -0.08074(6) 0.05111(10) 0.18046(6) 0.0275(3) Uani 1 1 d . . . . . F6 F -0.03366(6) 0.21502(10) 0.17898(6) 0.0305(3) Uani 1 1 d . . . . . F7 F -0.11941(6) 0.16461(14) 0.10148(6) 0.0429(4) Uani 1 1 d . . . . . N1 N 0.07676(7) -0.14446(12) 0.10212(7) 0.0131(3) Uani 1 1 d . . . . . N2 N 0.13631(7) 0.03382(11) 0.10386(6) 0.0128(3) Uani 1 1 d . . . . . N3 N 0.20438(8) 0.36278(12) 0.09290(8) 0.0208(3) Uani 1 1 d . . . . . N501 N 0.56075(7) -0.08361(14) -0.07034(8) 0.0206(3) Uani 1 1 d . . . . . C1 C 0.11523(7) -0.19780(13) 0.07262(7) 0.0116(3) Uani 1 1 d . . . . . C2 C 0.39450(7) -0.18041(13) -0.05776(7) 0.0118(3) Uani 1 1 d . . . . . C3 C 0.35247(8) -0.12669(13) -0.03110(8) 0.0122(3) Uani 1 1 d . . . . . H3 H 0.3592(10) -0.0437(18) -0.0232(10) 0.015 Uiso 1 1 d R . . . . C4 C 0.30062(7) -0.18608(13) -0.01522(7) 0.0110(3) Uani 1 1 d . . . . . C5 C 0.20901(7) -0.19444(13) 0.02934(7) 0.0106(3) Uani 1 1 d . . . . . C6 C 0.16690(7) -0.13720(13) 0.05825(7) 0.0109(3) Uani 1 1 d . . . . . C7 C 0.17507(8) -0.01824(13) 0.07426(7) 0.0113(3) Uani 1 1 d . . . . . C8 C 0.22747(8) 0.04694(13) 0.06069(7) 0.0118(3) Uani 1 1 d . . . . . C9 C 0.26686(8) -0.00933(13) 0.03179(8) 0.0121(3) Uani 1 1 d . . . . . H9 H 0.3007(10) 0.0332(18) 0.0221(10) 0.015 Uiso 1 1 d R . . . . C10 C 0.25943(7) -0.12959(13) 0.01486(7) 0.0109(3) Uani 1 1 d . . . . . C21 C 0.09128(8) -0.03393(13) 0.11633(8) 0.0128(3) Uani 1 1 d . . . . . C23 C 0.04976(8) 0.02353(13) 0.15255(8) 0.0132(3) Uani 1 1 d . . . . . C24 C -0.01828(8) 0.06974(14) 0.10995(8) 0.0159(3) Uani 1 1 d . . . . . C25 C -0.06363(8) 0.12648(15) 0.14391(8) 0.0183(3) Uani 1 1 d . . . . . C26 C 0.44650(8) -0.11095(13) -0.07287(8) 0.0128(3) Uani 1 1 d . . . . . C27 C 0.51275(8) -0.14768(15) -0.05918(8) 0.0168(3) Uani 1 1 d . . . . . H27 H 0.5245 -0.2221 -0.0410 0.020 Uiso 1 1 calc R . . . . C28 C 0.54297(9) 0.02033(16) -0.09711(9) 0.0198(3) Uani 1 1 d . . . . . H28 H 0.5762 0.0658 -0.1062 0.024 Uiso 1 1 calc R . . . . C29 C 0.47893(9) 0.06495(15) -0.11221(9) 0.0206(3) Uani 1 1 d . . . . . H29 H 0.4686 0.1393 -0.1309 0.025 Uiso 1 1 calc R . . . . C30 C 0.42993(8) -0.00135(14) -0.09945(8) 0.0169(3) Uani 1 1 d . . . . . H30 H 0.3856 0.0276 -0.1087 0.020 Uiso 1 1 calc R . . . . C31 C 0.24163(8) 0.17008(13) 0.07913(8) 0.0130(3) Uani 1 1 d . . . . . C32 C 0.19177(9) 0.25192(14) 0.07587(8) 0.0169(3) Uani 1 1 d . . . . . H32 H 0.1464 0.2274 0.0607 0.020 Uiso 1 1 calc R . . . . C33 C 0.26836(10) 0.39700(15) 0.11386(9) 0.0212(4) Uani 1 1 d . . . . . H33 H 0.2778 0.4750 0.1272 0.025 Uiso 1 1 calc R . . . . C34 C 0.32123(9) 0.32436(15) 0.11706(9) 0.0212(4) Uani 1 1 d . . . . . H34 H 0.3660 0.3525 0.1309 0.025 Uiso 1 1 calc R . . . . C35 C 0.30782(8) 0.20943(14) 0.09967(9) 0.0176(3) Uani 1 1 d . . . . . H35 H 0.3435 0.1577 0.1017 0.021 Uiso 1 1 calc R . . . . O41 O 0.21106(7) -0.12654(12) 0.22075(7) 0.0276(3) Uani 1 1 d . . . . . C41 C 0.21824(11) -0.24860(18) 0.23169(10) 0.0291(4) Uani 1 1 d . . . . . H41A H 0.1756 -0.2891 0.2103 0.035 Uiso 1 1 calc R . . . . H41B H 0.2319 -0.2657 0.2773 0.035 Uiso 1 1 calc R . . . . C42 C 0.27248(11) -0.28610(18) 0.20444(11) 0.0300(4) Uani 1 1 d . . . . . H42A H 0.2525 -0.3127 0.1604 0.036 Uiso 1 1 calc R . . . . H42B H 0.3000 -0.3493 0.2297 0.036 Uiso 1 1 calc R . . . . C43 C 0.31469(12) -0.1765(2) 0.20774(13) 0.0389(5) Uani 1 1 d . . . . . H43A H 0.3609 -0.1875 0.2368 0.047 Uiso 1 1 calc R . . . . H43B H 0.3166 -0.1554 0.1656 0.047 Uiso 1 1 calc R . . . . C44 C 0.27763(10) -0.08378(18) 0.23261(10) 0.0283(4) Uani 1 1 d . . . . . H44A H 0.2999 -0.0714 0.2783 0.034 Uiso 1 1 calc R . . . . H44B H 0.2769 -0.0094 0.2105 0.034 Uiso 1 1 calc R . . . . O51 O 0.5000 -0.0003(2) -0.2500 0.0383(5) Uani 1 2 d S T P B . C51 C 0.44200(13) -0.0724(2) -0.26110(11) 0.0380(5) Uani 1 1 d . . . . . H51A H 0.4071 -0.0501 -0.3009 0.046 Uiso 1 1 calc R . . A . H51B H 0.4232 -0.0647 -0.2262 0.046 Uiso 1 1 calc R . . A . C52 C 0.46494(16) -0.1953(3) -0.2651(2) 0.0747(11) Uani 1 1 d . . . B 2 H52A H 0.4428 -0.2491 -0.2437 0.090 Uiso 1 1 calc R . . B 2 H52B H 0.4540 -0.2194 -0.3097 0.090 Uiso 1 1 calc R . . B 2 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 F1 0.0276(6) 0.0210(5) 0.0215(5) 0.0067(4) 0.0165(5) 0.0067(4) F2 0.0164(5) 0.0252(5) 0.0267(6) -0.0145(4) 0.0098(4) -0.0060(4) F3 0.0160(5) 0.0365(6) 0.0273(6) -0.0164(5) 0.0046(4) -0.0020(5) F4 0.0332(6) 0.0315(6) 0.0260(6) 0.0134(5) 0.0184(5) 0.0136(5) F5 0.0274(6) 0.0263(6) 0.0397(7) 0.0014(5) 0.0256(5) 0.0003(5) F6 0.0296(6) 0.0218(5) 0.0476(8) -0.0133(5) 0.0227(6) -0.0017(5) F7 0.0272(6) 0.0735(10) 0.0258(6) 0.0031(6) 0.0055(5) 0.0317(7) N1 0.0113(6) 0.0131(6) 0.0166(7) -0.0016(5) 0.0070(5) 0.0003(5) N2 0.0116(6) 0.0128(6) 0.0156(7) -0.0014(5) 0.0065(5) 0.0002(5) N3 0.0229(7) 0.0113(6) 0.0317(9) 0.0005(6) 0.0134(7) 0.0029(5) N501 0.0137(7) 0.0228(7) 0.0287(8) -0.0055(6) 0.0114(6) -0.0045(6) C1 0.0096(6) 0.0126(7) 0.0133(7) -0.0008(5) 0.0047(5) 0.0002(5) C2 0.0095(6) 0.0127(7) 0.0141(7) -0.0002(5) 0.0052(6) -0.0017(5) C3 0.0104(6) 0.0114(6) 0.0162(7) -0.0013(5) 0.0061(6) -0.0020(5) C4 0.0095(6) 0.0113(6) 0.0130(7) -0.0016(5) 0.0048(5) -0.0020(5) C5 0.0095(6) 0.0099(6) 0.0129(7) -0.0014(5) 0.0044(5) -0.0010(5) C6 0.0088(6) 0.0115(6) 0.0135(7) -0.0009(5) 0.0051(5) -0.0002(5) C7 0.0107(6) 0.0110(6) 0.0125(7) -0.0004(5) 0.0041(6) -0.0006(5) C8 0.0108(7) 0.0109(6) 0.0143(7) -0.0005(5) 0.0048(6) -0.0008(5) C9 0.0119(7) 0.0104(6) 0.0156(7) -0.0012(5) 0.0063(6) -0.0018(5) C10 0.0102(6) 0.0102(6) 0.0133(7) -0.0016(5) 0.0053(5) -0.0011(5) C21 0.0109(7) 0.0143(7) 0.0147(7) -0.0008(5) 0.0060(6) 0.0010(5) C23 0.0148(7) 0.0117(6) 0.0152(7) -0.0019(5) 0.0078(6) -0.0015(5) C24 0.0155(7) 0.0184(7) 0.0154(8) -0.0002(6) 0.0071(6) 0.0017(6) C25 0.0140(7) 0.0213(8) 0.0206(8) 0.0002(6) 0.0071(6) 0.0043(6) C26 0.0113(7) 0.0137(7) 0.0160(7) -0.0035(6) 0.0079(6) -0.0024(5) C27 0.0117(7) 0.0174(7) 0.0228(8) -0.0019(6) 0.0075(6) -0.0007(6) C28 0.0169(8) 0.0225(8) 0.0236(9) -0.0057(7) 0.0117(7) -0.0090(6) C29 0.0209(8) 0.0170(8) 0.0269(9) -0.0003(7) 0.0119(7) -0.0050(6) C30 0.0146(7) 0.0156(7) 0.0224(8) 0.0007(6) 0.0085(6) -0.0011(6) C31 0.0144(7) 0.0104(6) 0.0159(7) -0.0002(5) 0.0075(6) -0.0002(5) C32 0.0154(7) 0.0138(7) 0.0230(9) 0.0014(6) 0.0084(6) 0.0012(6) C33 0.0265(9) 0.0118(7) 0.0285(10) -0.0028(6) 0.0134(8) -0.0023(6) C34 0.0183(8) 0.0156(7) 0.0311(10) -0.0046(7) 0.0097(7) -0.0059(6) C35 0.0146(7) 0.0133(7) 0.0268(9) -0.0030(6) 0.0093(7) -0.0006(6) O41 0.0236(7) 0.0254(7) 0.0329(8) 0.0019(6) 0.0081(6) 0.0028(5) C41 0.0346(11) 0.0262(9) 0.0256(10) 0.0037(8) 0.0087(8) -0.0014(8) C42 0.0297(10) 0.0260(10) 0.0305(11) 0.0006(8) 0.0044(8) 0.0054(8) C43 0.0293(11) 0.0364(12) 0.0517(15) -0.0029(10) 0.0140(11) 0.0005(9) C44 0.0268(10) 0.0279(10) 0.0266(10) -0.0027(8) 0.0036(8) -0.0019(8) O51 0.0536(15) 0.0301(11) 0.0363(12) 0.000 0.0216(11) 0.000 C51 0.0427(13) 0.0440(13) 0.0294(11) 0.0028(10) 0.0146(10) 0.0025(10) C52 0.0517(18) 0.0385(15) 0.128(3) 0.0266(19) 0.020(2) 0.0013(13) 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' F F 0.0171 0.0103 '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 C21 N1 C1 115.33(13) . . C21 N2 C7 115.43(14) . . C33 N3 C32 117.91(15) . . C28 N501 C27 117.32(15) . . N1 C1 C2 119.62(14) . 7_545 N1 C1 C6 120.96(14) . . C6 C1 C2 119.37(13) . 7_545 C1 C2 C26 122.26(13) 7_545 . C3 C2 C1 118.60(14) . 7_545 C3 C2 C26 119.08(14) . . C2 C3 H3 116.6(12) . . C2 C3 C4 123.18(14) . . C4 C3 H3 120.3(12) . . C5 C4 C3 118.52(13) 7_545 . C5 C4 C10 119.27(13) 7_545 . C10 C4 C3 122.20(14) . . C4 C5 C6 119.35(13) 7_545 . C4 C5 C10 121.74(13) 7_545 . C6 C5 C10 118.91(13) . . C1 C6 C5 120.95(14) . . C7 C6 C1 117.43(13) . . C7 C6 C5 121.62(13) . . N2 C7 C6 120.89(14) . . N2 C7 C8 119.78(14) . . C6 C7 C8 119.29(13) . . C7 C8 C31 122.52(13) . . C9 C8 C7 118.24(14) . . C9 C8 C31 119.20(14) . . C8 C9 H9 118.7(12) . . C8 C9 C10 123.55(14) . . C10 C9 H9 117.8(12) . . C4 C10 C5 118.99(13) . . C4 C10 C9 122.64(13) . . C5 C10 C9 118.36(13) . . N1 C21 N2 129.87(14) . . N1 C21 C23 114.74(13) . . N2 C21 C23 115.39(14) . . F1 C23 C21 110.27(13) . . F1 C23 C24 107.32(13) . . F2 C23 F1 107.78(13) . . F2 C23 C21 110.62(13) . . F2 C23 C24 107.00(13) . . C21 C23 C24 113.60(14) . . F3 C24 C23 109.36(13) . . F3 C24 C25 106.90(14) . . F4 C24 F3 107.98(14) . . F4 C24 C23 108.76(13) . . F4 C24 C25 107.36(14) . . C23 C24 C25 116.20(14) . . F5 C25 F7 107.86(15) . . F5 C25 C24 111.25(14) . . F6 C25 F5 108.29(15) . . F6 C25 F7 108.25(15) . . F6 C25 C24 111.61(14) . . F7 C25 C24 109.45(15) . . C27 C26 C2 123.13(15) . . C30 C26 C2 119.14(14) . . C30 C26 C27 117.67(14) . . N501 C27 C26 123.61(16) . . N501 C27 H27 118.2 . . C26 C27 H27 118.2 . . N501 C28 H28 118.2 . . N501 C28 C29 123.61(15) . . C29 C28 H28 118.2 . . C28 C29 H29 120.7 . . C28 C29 C30 118.53(17) . . C30 C29 H29 120.7 . . C26 C30 H30 120.4 . . C29 C30 C26 119.24(16) . . C29 C30 H30 120.4 . . C32 C31 C8 123.57(15) . . C35 C31 C8 119.55(14) . . C35 C31 C32 116.86(15) . . N3 C32 C31 123.72(16) . . N3 C32 H32 118.1 . . C31 C32 H32 118.1 . . N3 C33 H33 118.5 . . N3 C33 C34 123.07(16) . . C34 C33 H33 118.5 . . C33 C34 H34 120.7 . . C33 C34 C35 118.68(17) . . C35 C34 H34 120.7 . . C31 C35 H35 120.2 . . C34 C35 C31 119.70(15) . . C34 C35 H35 120.2 . . C44 O41 C41 105.38(15) . . O41 C41 H41A 110.7 . . O41 C41 H41B 110.7 . . O41 C41 C42 105.23(17) . . H41A C41 H41B 108.8 . . C42 C41 H41A 110.7 . . C42 C41 H41B 110.7 . . C41 C42 H42A 110.9 . . C41 C42 H42B 110.9 . . C41 C42 C43 104.20(17) . . H42A C42 H42B 108.9 . . C43 C42 H42A 110.9 . . C43 C42 H42B 110.9 . . C42 C43 H43A 111.0 . . C42 C43 H43B 111.0 . . H43A C43 H43B 109.0 . . C44 C43 C42 103.73(18) . . C44 C43 H43A 111.0 . . C44 C43 H43B 111.0 . . O41 C44 C43 106.06(17) . . O41 C44 H44A 110.5 . . O41 C44 H44B 110.5 . . C43 C44 H44A 110.5 . . C43 C44 H44B 110.5 . . H44A C44 H44B 108.7 . . C51 O51 C51 109.0(3) 2_654 . O51 C51 H51A 110.4 . . O51 C51 H51B 110.4 . . O51 C51 C52 106.5(2) . . H51A C51 H51B 108.6 . . C52 C51 H51A 110.4 . . C52 C51 H51B 110.4 . . C51 C52 H52A 110.5 . . C51 C52 H52B 110.5 . . C52 C52 C51 106.1(2) 2_654 . C52 C52 H52A 110.5 2_654 . C52 C52 H52B 110.5 2_654 . H52A C52 H52B 108.7 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 F1 C23 1.3507(19) . F2 C23 1.3498(18) . F3 C24 1.352(2) . F4 C24 1.348(2) . F5 C25 1.324(2) . F6 C25 1.320(2) . F7 C25 1.327(2) . N1 C1 1.3507(19) . N1 C21 1.328(2) . N2 C7 1.350(2) . N2 C21 1.329(2) . N3 C32 1.338(2) . N3 C33 1.337(2) . N501 C27 1.342(2) . N501 C28 1.341(2) . C1 C2 1.445(2) 7_545 C1 C6 1.418(2) . C2 C1 1.445(2) 7_545 C2 C3 1.369(2) . C2 C26 1.484(2) . C3 H3 0.98(2) . C3 C4 1.431(2) . C4 C5 1.416(2) 7_545 C4 C10 1.420(2) . C5 C4 1.416(2) 7_545 C5 C6 1.421(2) . C5 C10 1.422(2) . C6 C7 1.417(2) . C7 C8 1.449(2) . C8 C9 1.372(2) . C8 C31 1.485(2) . C9 H9 0.95(2) . C9 C10 1.435(2) . C21 C23 1.526(2) . C23 C24 1.540(2) . C24 C25 1.548(2) . C26 C27 1.396(2) . C26 C30 1.395(2) . C27 H27 0.9500 . C28 H28 0.9500 . C28 C29 1.382(3) . C29 H29 0.9500 . C29 C30 1.389(2) . C30 H30 0.9500 . C31 C32 1.399(2) . C31 C35 1.397(2) . C32 H32 0.9500 . C33 H33 0.9500 . C33 C34 1.379(3) . C34 H34 0.9500 . C34 C35 1.387(2) . C35 H35 0.9500 . O41 C41 1.431(2) . O41 C44 1.430(3) . C41 H41A 0.9900 . C41 H41B 0.9900 . C41 C42 1.524(3) . C42 H42A 0.9900 . C42 H42B 0.9900 . C42 C43 1.536(3) . C43 H43A 0.9900 . C43 H43B 0.9900 . C43 C44 1.534(3) . C44 H44A 0.9900 . C44 H44B 0.9900 . O51 C51 1.434(3) . O51 C51 1.434(3) 2_654 C51 H51A 0.9900 . C51 H51B 0.9900 . C51 C52 1.512(4) . C52 C52 1.414(7) 2_654 C52 H52A 0.9900 . C52 H52B 0.9900 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 F1 C23 C24 F3 -64.66(16) . . F1 C23 C24 F4 177.64(12) . . F1 C23 C24 C25 56.42(18) . . F2 C23 C24 F3 179.88(12) . . F2 C23 C24 F4 62.18(16) . . F2 C23 C24 C25 -59.04(17) . . F3 C24 C25 F5 59.90(18) . . F3 C24 C25 F6 -179.02(14) . . F3 C24 C25 F7 -59.20(19) . . F4 C24 C25 F5 175.56(14) . . F4 C24 C25 F6 -63.36(19) . . F4 C24 C25 F7 56.46(19) . . N1 C1 C6 C5 177.62(15) . . N1 C1 C6 C7 -1.9(2) . . N1 C21 C23 F1 36.01(19) . . N1 C21 C23 F2 155.14(14) . . N1 C21 C23 C24 -84.50(18) . . N2 C7 C8 C9 178.60(15) . . N2 C7 C8 C31 1.1(2) . . N2 C21 C23 F1 -143.96(15) . . N2 C21 C23 F2 -24.8(2) . . N2 C21 C23 C24 95.53(17) . . N3 C33 C34 C35 -2.1(3) . . N501 C28 C29 C30 -0.4(3) . . C1 N1 C21 N2 2.9(3) . . C1 N1 C21 C23 -177.08(14) . . C1 C2 C3 C4 2.2(2) 7_545 . C1 C2 C26 C27 -47.4(2) 7_545 . C1 C2 C26 C30 135.59(17) 7_545 . C1 C6 C7 N2 2.0(2) . . C1 C6 C7 C8 179.71(14) . . C2 C1 C6 C5 0.2(2) 7_545 . C2 C1 C6 C7 -179.34(14) 7_545 . C2 C3 C4 C5 -1.8(2) . 7_545 C2 C3 C4 C10 177.27(16) . . C2 C26 C27 N501 -177.24(16) . . C2 C26 C30 C29 178.44(15) . . C3 C2 C26 C27 135.26(17) . . C3 C2 C26 C30 -41.8(2) . . C3 C4 C10 C5 -179.82(15) . . C3 C4 C10 C9 -0.3(2) . . C4 C5 C6 C1 -0.5(2) 7_545 . C4 C5 C6 C7 179.00(15) 7_545 . C4 C5 C10 C4 0.7(3) 7_545 . C4 C5 C10 C9 -178.81(15) 7_545 . C5 C4 C10 C5 -0.7(2) 7_545 . C5 C4 C10 C9 178.81(15) 7_545 . C5 C6 C7 N2 -177.47(15) . . C5 C6 C7 C8 0.2(2) . . C6 C5 C10 C4 -178.69(14) . . C6 C5 C10 C9 1.8(2) . . C6 C7 C8 C9 0.9(2) . . C6 C7 C8 C31 -176.58(15) . . C7 N2 C21 N1 -2.7(3) . . C7 N2 C21 C23 177.22(14) . . C7 C8 C9 C10 -0.7(2) . . C7 C8 C31 C32 -38.8(2) . . C7 C8 C31 C35 142.70(17) . . C8 C9 C10 C4 179.79(15) . . C8 C9 C10 C5 -0.7(2) . . C8 C31 C32 N3 179.48(16) . . C8 C31 C35 C34 -179.87(16) . . C9 C8 C31 C32 143.69(17) . . C9 C8 C31 C35 -34.8(2) . . C10 C5 C6 C1 178.95(15) . . C10 C5 C6 C7 -1.5(2) . . C21 N1 C1 C2 177.13(15) . 7_545 C21 N1 C1 C6 -0.3(2) . . C21 N2 C7 C6 0.0(2) . . C21 N2 C7 C8 -177.63(14) . . C21 C23 C24 F3 57.50(17) . . C21 C23 C24 F4 -60.20(17) . . C21 C23 C24 C25 178.58(14) . . C23 C24 C25 F5 -62.48(19) . . C23 C24 C25 F6 58.6(2) . . C23 C24 C25 F7 178.42(15) . . C26 C2 C3 C4 179.61(15) . . C27 N501 C28 C29 1.5(3) . . C27 C26 C30 C29 1.3(2) . . C28 N501 C27 C26 -1.2(3) . . C28 C29 C30 C26 -1.0(3) . . C30 C26 C27 N501 -0.2(3) . . C31 C8 C9 C10 176.90(15) . . C32 N3 C33 C34 1.7(3) . . C32 C31 C35 C34 1.6(3) . . C33 N3 C32 C31 0.4(3) . . C33 C34 C35 C31 0.3(3) . . C35 C31 C32 N3 -2.0(3) . . O41 C41 C42 C43 26.0(2) . . C41 O41 C44 C43 37.3(2) . . C41 C42 C43 C44 -3.7(2) . . C42 C43 C44 O41 -19.8(2) . . C44 O41 C41 C42 -39.7(2) . . O51 C51 C52 C52 20.4(5) . 2_654 C51 O51 C51 C52 -7.4(2) 2_654 .