#------------------------------------------------------------------------------ #$Date: 2021-05-26 06:23:52 +0300 (Wed, 26 May 2021) $ #$Revision: 265492 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060689.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_7060689 loop_ _publ_author_name 'Yadav, Rahul' 'Parvin, Tasneem' _publ_section_title ; Multicomponent synthesis of styryl linked benzo[h]pyrazolo[3,4-b]quinoline-5,6(10H)-diones by liquid assisted grinding ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ00770J _journal_year 2021 _chemical_formula_moiety 'C29 H18 F N3 O2' _chemical_formula_sum 'C29 H18 F N3 O2' _chemical_formula_weight 459.46 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-02-05 deposited with the CCDC. 2021-05-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 123.03(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.177(4) _cell_length_b 12.753(5) _cell_length_c 11.653(4) _cell_measurement_reflns_used 5942 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.38 _cell_measurement_theta_min 2.65 _cell_volume 1143.4(8) _computing_cell_refinement 'APEX3/SAINT (Bruker, 2016)' _computing_data_collection 'APEX3(Bruker, 2016)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2016)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker axs kappa apex3 Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2956 _diffrn_reflns_av_unetI/netI 0.2306 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10931 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 20.000 _diffrn_reflns_theta_max 20.000 _diffrn_reflns_theta_min 2.647 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_correction_T_min 0.6325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_description block _exptl_crystal_F_000 476 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.189 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Flack x determined using 260 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -2.5(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 316 _refine_ls_number_reflns 2133 _refine_ls_number_restraints 196 _refine_ls_restrained_S_all 0.994 _refine_ls_R_factor_all 0.2444 _refine_ls_R_factor_gt 0.0817 _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^)+(0.0785P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1479 _refine_ls_wR_factor_ref 0.2121 _reflns_Friedel_coverage 0.982 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.992 _reflns_number_gt 833 _reflns_number_total 2133 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj00770j2.cif _cod_data_source_block NEW _cod_original_cell_volume 1143.3(8) _cod_original_sg_symbol_H-M 'P c' _cod_database_code 7060689 _shelx_shelxl_version_number 2018/3 _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_min 0.982 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL NEW_a.res in Pc NEW.res created by SHELXL-2018/3 at 15:53:13 on 17-Dec-2019 CELL 0.71073 9.1770 12.7533 11.6527 90.000 123.035 90.000 ZERR 2.00 0.0040 0.0051 0.0040 0.000 0.024 0.000 LATT -1 SYMM X, - Y, 1/2 + Z SFAC C H F N O UNIT 58 36 2 6 4 MERG 2 OMIT -3.00 40.00 DFIX 1.40 0.02 C11 C12 C18 C19 RIGU 0.002 0.004 C8 > C19 RIGU 0.002 0.004 C20 > N3 RIGU 0.002 0.004 C1 > C6 RIGU 0.002 0.004 C23 > C28 FMAP 2 PLAN 20 SIZE 0.10 0.20 0.20 ACTA BOND $H CONF L.S. 10 TEMP 25.00 WGHT 0.078500 FVAR 0.47439 C1 1 0.906849 0.153105 0.584288 11.00000 0.06986 0.07713 = 0.09168 -0.00428 0.03292 0.01917 AFIX 43 H1 2 0.925434 0.172674 0.668163 11.00000 -1.20000 AFIX 0 C2 1 1.007127 0.066496 0.577960 11.00000 0.09249 0.06848 = 0.14734 0.00403 0.07367 0.01765 AFIX 43 H2 2 1.089580 0.028807 0.654649 11.00000 -1.20000 AFIX 0 C3 1 0.967801 0.045806 0.446941 11.00000 0.13661 0.05075 = 0.15671 0.00786 0.09760 0.01035 C4 1 0.855671 0.099544 0.332885 11.00000 0.11275 0.03568 = 0.14207 -0.00404 0.09937 -0.00878 AFIX 43 H4 2 0.840417 0.082206 0.249471 11.00000 -1.20000 AFIX 0 C5 1 0.761805 0.182589 0.342246 11.00000 0.10774 0.03882 = 0.10157 -0.00438 0.07177 -0.00134 AFIX 43 H5 2 0.684497 0.221585 0.264976 11.00000 -1.20000 AFIX 0 C6 1 0.785362 0.205831 0.467316 11.00000 0.04492 0.07384 = 0.08436 -0.00519 0.03895 0.00479 C7 1 0.692653 0.294185 0.486717 11.00000 0.04203 0.06387 = 0.05998 -0.00817 0.04003 -0.00020 AFIX 43 H7 2 0.715194 0.302874 0.574226 11.00000 -1.20000 AFIX 0 C8 1 0.582601 0.360681 0.392407 11.00000 0.03505 0.06465 = 0.07584 0.00706 0.03031 0.00727 AFIX 43 H8 2 0.555109 0.352901 0.303353 11.00000 -1.20000 AFIX 0 C9 1 0.501548 0.446701 0.422422 11.00000 0.02894 0.05674 = 0.07229 0.00782 0.02733 0.00559 C10 1 0.524045 0.555950 0.403481 11.00000 0.01793 0.05621 = 0.03513 -0.00164 -0.00029 -0.00433 C11 1 0.630996 0.584718 0.345857 11.00000 0.06277 0.04870 = 0.06766 -0.00324 0.04042 0.00106 C12 1 0.654799 0.700347 0.335557 11.00000 0.08358 0.04940 = 0.09354 -0.01991 0.05604 -0.01644 C13 1 0.577422 0.779258 0.376929 11.00000 0.06365 0.04501 = 0.06678 -0.00864 0.03451 -0.01006 C14 1 0.593347 0.889023 0.361846 11.00000 0.05736 0.04798 = 0.14159 -0.00201 0.06172 -0.01007 AFIX 43 H14 2 0.655845 0.912137 0.325219 11.00000 -1.20000 AFIX 0 C15 1 0.516524 0.960958 0.401313 11.00000 0.12237 0.04946 = 0.21240 -0.00336 0.12111 -0.00209 AFIX 43 H15 2 0.534460 1.031937 0.395053 11.00000 -1.20000 AFIX 0 C16 1 0.414652 0.932606 0.449484 11.00000 0.12144 0.05376 = 0.19145 -0.02615 0.11348 -0.01837 AFIX 43 H16 2 0.357839 0.983649 0.468010 11.00000 -1.20000 AFIX 0 C17 1 0.396520 0.824158 0.470956 11.00000 0.06647 0.05511 = 0.12341 -0.02367 0.05698 -0.01549 AFIX 43 H17 2 0.334801 0.803806 0.509366 11.00000 -1.20000 AFIX 0 C18 1 0.475442 0.748273 0.431972 11.00000 0.06628 0.05497 = 0.07035 0.00760 0.03884 0.00671 C19 1 0.453221 0.633795 0.447282 11.00000 0.06387 0.05571 = 0.07273 0.00710 0.04146 0.00450 C20 1 0.333511 0.510863 0.513587 11.00000 0.03865 0.05998 = 0.05791 -0.00068 0.02877 -0.00124 C21 1 0.399804 0.426820 0.476738 11.00000 0.04834 0.05419 = 0.07510 -0.00009 0.03630 0.00085 C22 1 0.332774 0.335065 0.506619 11.00000 0.04138 0.05296 = 0.05945 0.00321 0.02558 0.00535 N2 4 0.235214 0.470989 0.558202 11.00000 0.06257 0.05216 = 0.07976 0.00042 0.05376 0.00390 N3 4 0.237727 0.362262 0.558841 11.00000 0.04848 0.05263 = 0.05976 0.00558 0.03197 0.00347 C23 1 0.136093 0.519076 0.605444 11.00000 0.04611 0.06096 = 0.08341 -0.01240 0.03541 -0.00382 C24 1 0.113203 0.629341 0.595862 11.00000 0.05446 0.06187 = 0.06529 -0.00965 0.03850 -0.00199 AFIX 43 H24 2 0.160069 0.671320 0.558525 11.00000 -1.20000 AFIX 0 C25 1 0.018374 0.671730 0.644323 11.00000 0.05677 0.07794 = 0.07406 -0.01868 0.03890 0.00337 AFIX 43 H25 2 0.003165 0.744035 0.640352 11.00000 -1.20000 AFIX 0 C26 1 -0.056821 0.609676 0.699902 11.00000 0.09707 0.09258 = 0.09038 -0.01744 0.07083 0.00469 AFIX 43 H26 2 -0.120537 0.640571 0.731340 11.00000 -1.20000 AFIX 0 C27 1 -0.033416 0.502214 0.706379 11.00000 0.04365 0.08691 = 0.11944 -0.01765 0.05364 -0.01153 AFIX 43 H27 2 -0.079135 0.459213 0.743703 11.00000 -1.20000 AFIX 0 C28 1 0.061004 0.459917 0.655202 11.00000 0.04746 0.06323 = 0.10654 -0.00105 0.04699 0.00554 AFIX 43 H28 2 0.072453 0.387442 0.655571 11.00000 -1.20000 AFIX 0 C29 1 0.350939 0.219836 0.482482 11.00000 0.10597 0.02961 = 0.14079 -0.00608 0.09379 0.00045 AFIX 33 H29A 2 0.421727 0.213519 0.445382 11.00000 -1.50000 H29B 2 0.404514 0.182525 0.567681 11.00000 -1.50000 H29C 2 0.238030 0.190800 0.419162 11.00000 -1.50000 AFIX 0 F1 3 1.061497 -0.037177 0.437161 11.00000 0.11405 0.10025 = 0.26306 -0.04168 0.11700 0.02109 N1 4 0.352284 0.614552 0.499160 11.00000 0.06161 0.04184 = 0.07646 -0.00159 0.04980 -0.01366 O1 5 0.692296 0.523744 0.304742 11.00000 0.11267 0.05414 = 0.11827 0.00687 0.09307 0.00635 O2 5 0.749450 0.729168 0.295466 11.00000 0.10035 0.04824 = 0.11178 -0.00180 0.07590 -0.02576 HKLF 4 REM NEW_a.res in Pc REM wR2 = 0.2121, GooF = S = 1.026, Restrained GooF = 0.994 for all data REM R1 = 0.0817 for 833 Fo > 4sig(Fo) and 0.2444 for all 2133 data REM 316 parameters refined using 196 restraints END WGHT 0.0911 0.0000 REM Highest difference peak 0.189, deepest hole -0.245, 1-sigma level 0.054 Q1 1 0.5003 0.5640 0.2717 11.00000 0.05 0.19 Q2 1 0.1714 0.5000 0.3877 11.00000 0.05 0.18 Q3 1 0.4085 0.4639 0.3137 11.00000 0.05 0.18 Q4 1 -0.2238 0.4830 0.5377 11.00000 0.05 0.18 Q5 1 0.4793 1.0558 0.6145 11.00000 0.05 0.18 Q6 1 0.8436 0.5484 0.4844 11.00000 0.05 0.17 Q7 1 0.5717 0.4652 0.5492 11.00000 0.05 0.17 Q8 1 0.1804 0.8059 0.6009 11.00000 0.05 0.17 Q9 1 0.6346 0.4786 0.1481 11.00000 0.05 0.17 Q10 1 -0.0227 0.4834 0.5411 11.00000 0.05 0.17 Q11 1 0.1658 0.6274 0.3709 11.00000 0.05 0.16 Q12 1 0.3499 0.3861 0.1822 11.00000 0.05 0.16 Q13 1 0.5724 0.0755 0.2444 11.00000 0.05 0.16 Q14 1 0.3404 0.9240 0.6601 11.00000 0.05 0.16 Q15 1 0.8598 0.2124 0.7035 11.00000 0.05 0.16 Q16 1 -0.0301 0.3556 0.8585 11.00000 0.05 0.16 Q17 1 0.7181 0.0545 0.1219 11.00000 0.05 0.16 Q18 1 0.2395 0.3245 0.3301 11.00000 0.05 0.16 Q19 1 0.8844 -0.1086 0.3737 11.00000 0.05 0.16 Q20 1 0.2540 0.1947 0.6237 11.00000 0.05 0.15 ; _shelx_res_checksum 80642 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, 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 C1 C 0.907(4) 0.153(2) 0.584(3) 0.085(10) Uani 1 1 d . . . . . H1 H 0.925434 0.172674 0.668163 0.102 Uiso 1 1 calc R U . . . C2 C 1.007(4) 0.066(2) 0.578(4) 0.098(10) Uani 1 1 d . . . . . H2 H 1.089580 0.028807 0.654649 0.118 Uiso 1 1 calc R U . . . C3 C 0.968(5) 0.046(2) 0.447(4) 0.106(12) Uani 1 1 d . . . . . C4 C 0.856(4) 0.0995(18) 0.333(4) 0.081(9) Uani 1 1 d . . . . . H4 H 0.840417 0.082206 0.249471 0.098 Uiso 1 1 calc R U . . . C5 C 0.762(4) 0.1826(18) 0.342(3) 0.075(9) Uani 1 1 d . . . . . H5 H 0.684497 0.221585 0.264976 0.090 Uiso 1 1 calc R U . . . C6 C 0.785(3) 0.206(2) 0.467(3) 0.066(8) Uani 1 1 d . . . . . C7 C 0.693(3) 0.2942(18) 0.487(3) 0.049(8) Uani 1 1 d . . . . . H7 H 0.715194 0.302874 0.574226 0.059 Uiso 1 1 calc R U . . . C8 C 0.583(3) 0.361(2) 0.392(3) 0.058(9) Uani 1 1 d . . . . . H8 H 0.555109 0.352901 0.303353 0.070 Uiso 1 1 calc R U . . . C9 C 0.502(3) 0.447(2) 0.422(3) 0.053(8) Uani 1 1 d . . . . . C10 C 0.524(3) 0.556(2) 0.403(2) 0.044(7) Uani 1 1 d . . . . . C11 C 0.631(4) 0.585(2) 0.346(3) 0.057(8) Uani 1 1 d D . . . . C12 C 0.655(4) 0.700(2) 0.336(3) 0.071(9) Uani 1 1 d D . . . . C13 C 0.577(3) 0.779(2) 0.377(3) 0.059(8) Uani 1 1 d . . . . . C14 C 0.593(3) 0.8890(18) 0.362(3) 0.078(10) Uani 1 1 d . . . . . H14 H 0.655845 0.912137 0.325219 0.094 Uiso 1 1 calc R U . . . C15 C 0.517(4) 0.961(2) 0.401(4) 0.113(13) Uani 1 1 d . . . . . H15 H 0.534460 1.031937 0.395053 0.135 Uiso 1 1 calc R U . . . C16 C 0.415(4) 0.933(2) 0.449(4) 0.108(11) Uani 1 1 d . . . . . H16 H 0.357839 0.983649 0.468010 0.129 Uiso 1 1 calc R U . . . C17 C 0.397(4) 0.824(2) 0.471(3) 0.079(9) Uani 1 1 d . . . . . H17 H 0.334801 0.803806 0.509366 0.095 Uiso 1 1 calc R U . . . C18 C 0.475(3) 0.748(2) 0.432(3) 0.063(9) Uani 1 1 d D . . . . C19 C 0.453(4) 0.634(2) 0.447(3) 0.062(8) Uani 1 1 d D . . . . C20 C 0.334(3) 0.511(2) 0.514(3) 0.051(7) Uani 1 1 d . . . . . C21 C 0.400(3) 0.427(2) 0.477(3) 0.058(8) Uani 1 1 d . . . . . C22 C 0.333(3) 0.335(2) 0.507(3) 0.052(7) Uani 1 1 d . . . . . N2 N 0.235(3) 0.4710(14) 0.558(2) 0.057(6) Uani 1 1 d . . . . . N3 N 0.238(3) 0.3623(14) 0.559(2) 0.052(6) Uani 1 1 d . . . . . C23 C 0.136(3) 0.519(2) 0.605(3) 0.063(9) Uani 1 1 d . . . . . C24 C 0.113(3) 0.629(2) 0.596(2) 0.058(8) Uani 1 1 d . . . . . H24 H 0.160069 0.671320 0.558525 0.069 Uiso 1 1 calc R U . . . C25 C 0.018(3) 0.672(2) 0.644(3) 0.068(9) Uani 1 1 d . . . . . H25 H 0.003165 0.744035 0.640352 0.081 Uiso 1 1 calc R U . . . C26 C -0.057(4) 0.610(2) 0.700(3) 0.083(10) Uani 1 1 d . . . . . H26 H -0.120537 0.640571 0.731340 0.100 Uiso 1 1 calc R U . . . C27 C -0.033(3) 0.502(2) 0.706(3) 0.079(9) Uani 1 1 d . . . . . H27 H -0.079135 0.459213 0.743703 0.094 Uiso 1 1 calc R U . . . C28 C 0.061(3) 0.460(2) 0.655(3) 0.070(9) Uani 1 1 d . . . . . H28 H 0.072453 0.387442 0.655571 0.084 Uiso 1 1 calc R U . . . C29 C 0.351(3) 0.2198(17) 0.482(3) 0.078(10) Uani 1 1 d . . . . . H29A H 0.421727 0.213519 0.445382 0.118 Uiso 1 1 calc R U . . . H29B H 0.404514 0.182525 0.567681 0.118 Uiso 1 1 calc R U . . . H29C H 0.238030 0.190800 0.419162 0.118 Uiso 1 1 calc R U . . . F1 F 1.061(2) -0.0372(13) 0.437(2) 0.152(9) Uani 1 1 d . . . . . N1 N 0.352(3) 0.6146(15) 0.499(2) 0.054(7) Uani 1 1 d . . . . . O1 O 0.692(2) 0.5237(13) 0.305(2) 0.079(7) Uani 1 1 d . . . . . O2 O 0.749(2) 0.7292(12) 0.295(2) 0.077(7) 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 C1 0.07(2) 0.08(2) 0.09(2) -0.004(16) 0.033(18) 0.019(14) C2 0.09(3) 0.07(2) 0.15(2) 0.00(2) 0.07(2) 0.018(16) C3 0.14(3) 0.05(2) 0.16(3) 0.008(18) 0.10(3) 0.010(18) C4 0.11(3) 0.036(18) 0.14(2) -0.004(16) 0.10(2) -0.009(14) C5 0.11(2) 0.039(17) 0.10(2) -0.004(16) 0.07(2) -0.001(15) C6 0.04(2) 0.07(2) 0.08(2) -0.005(15) 0.039(18) 0.005(15) C7 0.04(2) 0.064(18) 0.06(2) -0.008(17) 0.040(19) 0.000(16) C8 0.04(2) 0.065(16) 0.08(2) 0.007(18) 0.030(18) 0.007(15) C9 0.029(17) 0.057(11) 0.07(2) 0.008(16) 0.027(17) 0.006(13) C10 0.018(16) 0.056(10) 0.035(18) -0.002(13) 0.000(13) -0.004(12) C11 0.06(2) 0.049(11) 0.07(2) -0.003(16) 0.040(18) 0.001(15) C12 0.08(2) 0.049(11) 0.09(3) -0.020(17) 0.06(2) -0.016(15) C13 0.06(2) 0.045(11) 0.07(2) -0.009(15) 0.035(16) -0.010(13) C14 0.06(2) 0.048(11) 0.14(3) -0.002(17) 0.06(2) -0.010(14) C15 0.12(3) 0.049(16) 0.21(4) 0.00(2) 0.12(3) -0.002(19) C16 0.12(3) 0.054(12) 0.19(3) -0.03(2) 0.11(2) -0.018(19) C17 0.07(2) 0.055(12) 0.12(3) -0.024(17) 0.06(2) -0.015(15) C18 0.07(2) 0.055(11) 0.07(2) 0.008(15) 0.039(18) 0.007(14) C19 0.06(2) 0.056(10) 0.07(2) 0.007(15) 0.041(19) 0.005(14) C20 0.039(18) 0.060(13) 0.06(2) -0.001(16) 0.029(16) -0.001(14) C21 0.05(2) 0.054(13) 0.08(2) 0.000(16) 0.036(17) 0.001(14) C22 0.041(18) 0.053(12) 0.06(2) 0.003(14) 0.026(15) 0.005(13) N2 0.063(16) 0.052(9) 0.080(17) 0.000(13) 0.054(14) 0.004(12) N3 0.048(15) 0.053(9) 0.060(17) 0.006(13) 0.032(13) 0.003(12) C23 0.05(2) 0.061(12) 0.08(2) -0.012(16) 0.035(19) -0.004(14) C24 0.05(2) 0.062(12) 0.07(2) -0.010(16) 0.039(18) -0.002(14) C25 0.06(2) 0.078(17) 0.07(2) -0.019(17) 0.039(18) 0.003(16) C26 0.10(3) 0.093(15) 0.09(3) -0.017(19) 0.07(2) 0.005(18) C27 0.04(2) 0.087(15) 0.12(3) -0.018(18) 0.054(19) -0.012(16) C28 0.05(2) 0.063(16) 0.11(2) -0.001(16) 0.047(18) 0.006(15) C29 0.11(3) 0.030(16) 0.14(3) -0.006(18) 0.09(2) 0.000(16) F1 0.114(17) 0.100(14) 0.26(3) -0.042(15) 0.117(19) 0.021(12) N1 0.062(17) 0.042(14) 0.08(2) -0.002(13) 0.050(16) -0.014(13) O1 0.113(18) 0.054(12) 0.118(18) 0.007(12) 0.093(16) 0.006(12) O2 0.100(18) 0.048(12) 0.11(2) -0.002(12) 0.076(16) -0.026(12) 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 _geom_angle_publ_flag C6 C1 C2 121(3) . . ? C6 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 114(3) . . ? C3 C2 H2 123.1 . . ? C1 C2 H2 123.1 . . ? C4 C3 C2 126(4) . . ? C4 C3 F1 118(3) . . ? C2 C3 F1 115(4) . . ? C3 C4 C5 119(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 119(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C1 C6 C5 121(3) . . ? C1 C6 C7 116(3) . . ? C5 C6 C7 123(3) . . ? C8 C7 C6 127(3) . . ? C8 C7 H7 116.7 . . ? C6 C7 H7 116.7 . . ? C7 C8 C9 123(3) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C21 C9 C10 115(3) . . ? C21 C9 C8 121(3) . . ? C10 C9 C8 123(2) . . ? C9 C10 C19 119(3) . . ? C9 C10 C11 119(2) . . ? C19 C10 C11 122(2) . . ? O1 C11 C10 125(2) . . ? O1 C11 C12 119(3) . . ? C10 C11 C12 116(2) . . ? O2 C12 C13 119(2) . . ? O2 C12 C11 119(3) . . ? C13 C12 C11 122(3) . . ? C14 C13 C12 122(3) . . ? C14 C13 C18 117(2) . . ? C12 C13 C18 120(3) . . ? C15 C14 C13 120(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 123(3) . . ? C16 C15 H15 118.5 . . ? C14 C15 H15 118.5 . . ? C15 C16 C17 120(3) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 118(3) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C17 C18 C13 121(2) . . ? C17 C18 C19 120(3) . . ? C13 C18 C19 119(2) . . ? N1 C19 C10 126(2) . . ? N1 C19 C18 113(2) . . ? C10 C19 C18 121(3) . . ? N1 C20 N2 125(2) . . ? N1 C20 C21 127(3) . . ? N2 C20 C21 109(2) . . ? C9 C21 C20 120(3) . . ? C9 C21 C22 137(3) . . ? C20 C21 C22 103(2) . . ? N3 C22 C21 111(2) . . ? N3 C22 C29 120(2) . . ? C21 C22 C29 129(3) . . ? N3 N2 C20 111(2) . . ? N3 N2 C23 116(2) . . ? C20 N2 C23 133(2) . . ? C22 N3 N2 105(2) . . ? C28 C23 C24 120(3) . . ? C28 C23 N2 120(2) . . ? C24 C23 N2 119(2) . . ? C25 C24 C23 117(3) . . ? C25 C24 H24 121.4 . . ? C23 C24 H24 121.4 . . ? C24 C25 C26 123(3) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? C25 C26 C27 119(3) . . ? C25 C26 H26 120.7 . . ? C27 C26 H26 120.7 . . ? C28 C27 C26 118(3) . . ? C28 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? C23 C28 C27 123(3) . . ? C23 C28 H28 118.4 . . ? C27 C28 H28 118.4 . . ? C22 C29 H29A 109.5 . . ? C22 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C22 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C20 N1 C19 113(2) . . ? 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 C1 C6 1.38(3) . ? C1 C2 1.47(3) . ? C1 H1 0.9300 . ? C2 C3 1.39(4) . ? C2 H2 0.9300 . ? C3 C4 1.34(4) . ? C3 F1 1.41(3) . ? C4 C5 1.41(3) . ? C4 H4 0.9300 . ? C5 C6 1.38(3) . ? C5 H5 0.9300 . ? C6 C7 1.50(3) . ? C7 C8 1.32(3) . ? C7 H7 0.9300 . ? C8 C9 1.47(3) . ? C8 H8 0.9300 . ? C9 C21 1.41(3) . ? C9 C10 1.44(3) . ? C10 C19 1.42(3) . ? C10 C11 1.51(3) . ? C11 O1 1.20(3) . ? C11 C12 1.51(2) . ? C12 O2 1.25(3) . ? C12 C13 1.46(3) . ? C13 C14 1.43(3) . ? C13 C18 1.45(3) . ? C14 C15 1.38(3) . ? C14 H14 0.9300 . ? C15 C16 1.38(4) . ? C15 H15 0.9300 . ? C16 C17 1.43(3) . ? C16 H16 0.9300 . ? C17 C18 1.42(3) . ? C17 H17 0.9300 . ? C18 C19 1.50(2) . ? C19 N1 1.38(2) . ? C20 N1 1.36(3) . ? C20 N2 1.36(3) . ? C20 C21 1.41(3) . ? C21 C22 1.45(3) . ? C22 N3 1.35(3) . ? C22 C29 1.52(3) . ? N2 N3 1.39(2) . ? N2 C23 1.43(3) . ? C23 C28 1.35(3) . ? C23 C24 1.42(3) . ? C24 C25 1.38(3) . ? C24 H24 0.9300 . ? C25 C26 1.42(3) . ? C25 H25 0.9300 . ? C26 C27 1.38(3) . ? C26 H26 0.9300 . ? C27 C28 1.40(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0(4) . . . . ? C1 C2 C3 C4 3(5) . . . . ? C1 C2 C3 F1 -180(2) . . . . ? C2 C3 C4 C5 -3(5) . . . . ? F1 C3 C4 C5 -180(2) . . . . ? C3 C4 C5 C6 -1(4) . . . . ? C2 C1 C6 C5 -4(4) . . . . ? C2 C1 C6 C7 -179(2) . . . . ? C4 C5 C6 C1 4(4) . . . . ? C4 C5 C6 C7 179(2) . . . . ? C1 C6 C7 C8 174(3) . . . . ? C5 C6 C7 C8 -1(4) . . . . ? C6 C7 C8 C9 -178(2) . . . . ? C7 C8 C9 C21 -59(4) . . . . ? C7 C8 C9 C10 119(3) . . . . ? C21 C9 C10 C19 4(3) . . . . ? C8 C9 C10 C19 -174(3) . . . . ? C21 C9 C10 C11 180(2) . . . . ? C8 C9 C10 C11 2(4) . . . . ? C9 C10 C11 O1 5(4) . . . . ? C19 C10 C11 O1 -179(3) . . . . ? C9 C10 C11 C12 -177(2) . . . . ? C19 C10 C11 C12 -1(3) . . . . ? O1 C11 C12 O2 -6(4) . . . . ? C10 C11 C12 O2 176(3) . . . . ? O1 C11 C12 C13 177(3) . . . . ? C10 C11 C12 C13 -1(4) . . . . ? O2 C12 C13 C14 6(5) . . . . ? C11 C12 C13 C14 -177(3) . . . . ? O2 C12 C13 C18 -176(3) . . . . ? C11 C12 C13 C18 1(4) . . . . ? C12 C13 C14 C15 179(3) . . . . ? C18 C13 C14 C15 1(4) . . . . ? C13 C14 C15 C16 -4(6) . . . . ? C14 C15 C16 C17 5(6) . . . . ? C15 C16 C17 C18 -4(5) . . . . ? C16 C17 C18 C13 2(4) . . . . ? C16 C17 C18 C19 -177(3) . . . . ? C14 C13 C18 C17 -1(4) . . . . ? C12 C13 C18 C17 -179(3) . . . . ? C14 C13 C18 C19 179(2) . . . . ? C12 C13 C18 C19 1(4) . . . . ? C9 C10 C19 N1 -5(4) . . . . ? C11 C10 C19 N1 179(2) . . . . ? C9 C10 C19 C18 179(2) . . . . ? C11 C10 C19 C18 3(4) . . . . ? C17 C18 C19 N1 1(4) . . . . ? C13 C18 C19 N1 -179(2) . . . . ? C17 C18 C19 C10 177(3) . . . . ? C13 C18 C19 C10 -3(4) . . . . ? C10 C9 C21 C20 -2(4) . . . . ? C8 C9 C21 C20 176(2) . . . . ? C10 C9 C21 C22 176(3) . . . . ? C8 C9 C21 C22 -6(5) . . . . ? N1 C20 C21 C9 2(4) . . . . ? N2 C20 C21 C9 178(2) . . . . ? N1 C20 C21 C22 -177(3) . . . . ? N2 C20 C21 C22 -1(3) . . . . ? C9 C21 C22 N3 -179(3) . . . . ? C20 C21 C22 N3 -1(3) . . . . ? C9 C21 C22 C29 -2(5) . . . . ? C20 C21 C22 C29 177(3) . . . . ? N1 C20 N2 N3 178(2) . . . . ? C21 C20 N2 N3 3(3) . . . . ? N1 C20 N2 C23 -3(5) . . . . ? C21 C20 N2 C23 -179(3) . . . . ? C21 C22 N3 N2 2(3) . . . . ? C29 C22 N3 N2 -175(2) . . . . ? C20 N2 N3 C22 -3(3) . . . . ? C23 N2 N3 C22 178(2) . . . . ? N3 N2 C23 C28 4(4) . . . . ? C20 N2 C23 C28 -174(3) . . . . ? N3 N2 C23 C24 -174(3) . . . . ? C20 N2 C23 C24 7(5) . . . . ? C28 C23 C24 C25 3(4) . . . . ? N2 C23 C24 C25 -179(2) . . . . ? C23 C24 C25 C26 -1(4) . . . . ? C24 C25 C26 C27 0(5) . . . . ? C25 C26 C27 C28 -1(5) . . . . ? C24 C23 C28 C27 -4(5) . . . . ? N2 C23 C28 C27 178(3) . . . . ? C26 C27 C28 C23 3(5) . . . . ? N2 C20 N1 C19 -178(2) . . . . ? C21 C20 N1 C19 -3(4) . . . . ? C10 C19 N1 C20 4(4) . . . . ? C18 C19 N1 C20 -180(2) . . . . ?