#------------------------------------------------------------------------------ #$Date: 2017-06-22 06:15:01 +0300 (Thu, 22 Jun 2017) $ #$Revision: 198068 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546373.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_1546373 _journal_paper_doi 10.1039/C7NJ01698K _chemical_formula_sum 'C34 H31 N4 O3' _chemical_formula_weight 543.63 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-05-04 deposited with the CCDC. 2017-06-21 downloaded from the CCDC. ; _cell_angle_alpha 94.821(10) _cell_angle_beta 94.404(9) _cell_angle_gamma 108.372(9) _cell_formula_units_Z 2 _cell_length_a 7.990(3) _cell_length_b 12.475(4) _cell_length_c 14.539(5) _cell_measurement_reflns_used 2396 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 60 _cell_measurement_theta_min 5 _cell_volume 1362.3(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 43399 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.866 _diffrn_reflns_theta_min 2.702 _diffrn_source molybdene _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9558 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.325 _exptl_crystal_description platelet _exptl_crystal_F_000 574 _exptl_crystal_size_max 0.354 _exptl_crystal_size_mid 0.125 _exptl_crystal_size_min 0.092 _refine_diff_density_max 0.398 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 374 _refine_ls_number_reflns 5255 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0437 _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^)+(0.0488P)^2^+0.3717P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.1163 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3527 _reflns_number_total 5255 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7nj01698k2.cif _cod_data_source_block CA104 _cod_original_cell_volume 1362.2(8) _cod_database_code 1546373 _shelx_shelxl_version_number 2014/7 _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 0.970 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; AG104.res created by SHELXL-2014/7 TITL AG104_a.res in P-1 CELL 0.71073 7.9903 12.4746 14.5387 94.821 94.404 108.372 ZERR 2.00 0.0025 0.0042 0.0053 0.010 0.009 0.009 LATT 1 SFAC C H N O UNIT 68 62 8 6 LIST 6 TEMP 20.000 SIZE 0.092 0.125 0.354 L.S. 11 FMAP 2 OMIT 0 -1 1 OMIT 0 1 0 OMIT -1 1 0 OMIT 0 0 1 OMIT 0 1 1 OMIT 1 0 1 OMIT 0 0 2 OMIT 0 -1 2 PLAN 10 ACTA BOND $H WGHT 0.048800 0.371700 FVAR 0.38666 O001 4 0.462594 0.141501 0.439891 11.00000 0.02189 0.02283 = 0.02915 0.00867 0.00620 0.00349 O002 4 1.614138 0.907319 0.063462 11.00000 0.03038 0.03189 = 0.04605 0.01279 0.01230 -0.00459 O007 4 0.930119 0.456199 0.113141 11.00000 0.07352 0.06550 = 0.02896 0.00779 0.00437 -0.03600 N003 3 0.487068 0.173352 0.592340 11.00000 0.02097 0.02812 = 0.03136 0.00839 0.00408 0.00034 N004 3 0.615296 0.262595 0.558933 11.00000 0.02335 0.02861 = 0.03271 0.00982 0.00548 0.00260 N005 3 1.123047 0.578807 0.222567 11.00000 0.03296 0.03489 = 0.02635 0.01058 0.00429 -0.00502 AFIX 43 H005 2 1.155722 0.596251 0.281141 11.00000 -1.20000 AFIX 0 N006 3 1.502824 0.832566 0.103907 11.00000 0.02349 0.02315 = 0.02958 0.00601 0.00554 -0.00213 C008 1 0.400300 0.104550 0.520307 11.00000 0.01926 0.02613 = 0.02668 0.01036 0.00603 0.00724 C009 1 0.595454 0.239969 0.469689 11.00000 0.01798 0.02122 = 0.03167 0.00803 0.00347 0.00454 C00N 1 0.217302 -0.000718 0.680564 11.00000 0.02527 0.02848 = 0.02953 0.00575 0.00095 0.00101 AFIX 43 H00N 2 0.313637 0.065645 0.694425 11.00000 -1.20000 AFIX 0 C00Z 1 0.906719 0.471524 0.360766 11.00000 0.02917 0.02369 = 0.03562 0.00606 0.00473 -0.00300 AFIX 43 H00Z 2 0.987330 0.543753 0.379029 11.00000 -1.20000 AFIX 0 C00Q 1 0.980126 0.487983 0.194639 11.00000 0.03119 0.02992 = 0.03067 0.00921 0.00539 -0.00114 C00S 1 -0.299358 -0.354511 0.697041 11.00000 0.02646 0.03001 = 0.05934 0.01488 0.01580 0.00611 AFIX 43 H00S 2 -0.393194 -0.422454 0.685473 11.00000 -1.20000 AFIX 0 C00W 1 0.759573 0.319435 0.242899 11.00000 0.03265 0.02893 = 0.02834 0.00310 0.00548 0.00056 AFIX 43 H00W 2 0.740437 0.288424 0.181043 11.00000 -1.20000 AFIX 0 C00U 1 1.415258 0.647254 0.166927 11.00000 0.03325 0.02702 = 0.03827 0.00905 0.00858 0.00648 AFIX 23 H00A 2 1.413266 0.569231 0.154347 11.00000 -1.20000 H00B 2 1.468610 0.674547 0.230256 11.00000 -1.20000 AFIX 0 C00V 1 -0.275242 -0.351748 0.528516 11.00000 0.02216 0.02452 = 0.05497 0.00434 0.00282 0.00006 AFIX 43 H00V 2 -0.371866 -0.418069 0.515531 11.00000 -1.20000 AFIX 0 C00T 1 -0.193670 -0.302924 0.458088 11.00000 0.02520 0.02803 = 0.04071 -0.00164 -0.00245 0.00428 AFIX 43 H00T 2 -0.236428 -0.335165 0.397379 11.00000 -1.20000 AFIX 0 C00P 1 0.812281 0.410986 0.425704 11.00000 0.02984 0.02905 = 0.02821 0.00375 0.00457 0.00217 AFIX 43 H00P 2 0.829595 0.442724 0.487308 11.00000 -1.20000 AFIX 0 C00X 1 1.222681 0.830787 0.017707 11.00000 0.03364 0.03960 = 0.02961 0.01051 0.00112 0.00525 AFIX 137 H00C 2 1.118582 0.852689 0.022889 11.00000 -1.50000 H00D 2 1.188266 0.751678 -0.005430 11.00000 -1.50000 H00E 2 1.294528 0.875348 -0.024314 11.00000 -1.50000 AFIX 0 C00R 1 1.225978 0.649572 0.158546 11.00000 0.02876 0.02955 = 0.02608 0.00965 0.00682 -0.00157 AFIX 13 H00R 2 1.171028 0.620880 0.094883 11.00000 -1.20000 AFIX 0 C00B 1 -0.042384 -0.202353 0.474604 11.00000 0.01982 0.02088 = 0.03475 0.00402 0.00133 0.00761 C00F 1 1.328619 0.850886 0.113017 11.00000 0.02235 0.02621 = 0.02759 0.00538 0.00326 0.00316 C00G 1 0.046668 -0.152567 0.402310 11.00000 0.02818 0.02815 = 0.02668 -0.00028 0.00107 0.01041 AFIX 43 H00G 2 0.008828 -0.185969 0.341474 11.00000 -1.20000 AFIX 0 C00M 1 -0.017075 -0.151481 0.733817 11.00000 0.02575 0.03192 = 0.03161 0.01074 0.00758 0.01004 C00O 1 0.664532 0.258489 0.307709 11.00000 0.02916 0.02256 = 0.03245 0.00443 0.00626 -0.00080 AFIX 43 H00O 2 0.581804 0.187009 0.289287 11.00000 -1.20000 AFIX 0 C00D 1 0.250761 -0.001486 0.509898 11.00000 0.01927 0.02274 = 0.02889 0.00699 0.00313 0.00812 C00L 1 0.189726 -0.054684 0.420015 11.00000 0.02588 0.02763 = 0.02751 0.00811 0.00816 0.00998 AFIX 43 H00L 2 0.247316 -0.023122 0.370693 11.00000 -1.20000 AFIX 0 C00E 1 0.165452 -0.049258 0.585547 11.00000 0.01857 0.02322 = 0.02839 0.00533 0.00218 0.00858 C00C 1 -0.071985 -0.201859 0.641495 11.00000 0.01917 0.02537 = 0.03661 0.00905 0.00649 0.00929 C00K 1 1.229940 0.770989 0.179415 11.00000 0.02084 0.03587 = 0.02610 0.00783 0.00397 0.00489 AFIX 23 H00F 2 1.285764 0.799246 0.242208 11.00000 -1.20000 H00H 2 1.108929 0.772270 0.176875 11.00000 -1.20000 AFIX 0 C00I 1 -0.217467 -0.304477 0.622770 11.00000 0.01947 0.02592 = 0.04569 0.00867 0.00701 0.00748 C00H 1 0.692221 0.303606 0.399929 11.00000 0.01840 0.02239 = 0.03062 0.00815 0.00327 0.00667 C00J 1 0.017898 -0.150892 0.567013 11.00000 0.01807 0.02293 = 0.03190 0.00773 0.00425 0.00846 C00A 1 0.882914 0.426077 0.268905 11.00000 0.02369 0.02569 = 0.03202 0.01017 0.00623 0.00622 C00Y 1 -0.105098 -0.203868 0.805608 11.00000 0.04185 0.04209 = 0.03297 0.01204 0.01402 0.01274 AFIX 43 H00Y 2 -0.070021 -0.170243 0.866554 11.00000 -1.20000 AFIX 0 C010 1 1.530508 0.719280 0.100980 11.00000 0.02867 0.02530 = 0.04065 0.00526 0.00969 0.00577 C011 1 0.130063 -0.048756 0.750359 11.00000 0.03419 0.03724 = 0.02728 0.00516 0.00408 0.00534 AFIX 43 H011 2 0.166844 -0.013960 0.810889 11.00000 -1.20000 AFIX 0 C012 1 1.366878 0.973827 0.153650 11.00000 0.03973 0.03113 = 0.04350 0.00540 0.00552 0.01052 AFIX 137 H01A 2 1.257793 0.986006 0.166526 11.00000 -1.50000 H01B 2 1.421759 1.023734 0.109908 11.00000 -1.50000 H01C 2 1.445200 0.989245 0.210131 11.00000 -1.50000 AFIX 0 C013 1 -0.243645 -0.305032 0.787182 11.00000 0.03832 0.04164 = 0.04969 0.01978 0.02356 0.01223 AFIX 43 H013 2 -0.299513 -0.339867 0.835771 11.00000 -1.20000 AFIX 0 C014 1 1.487604 0.662769 0.001011 11.00000 0.05464 0.03543 = 0.04599 0.00155 0.02441 0.00895 AFIX 137 H01D 2 1.531966 0.599679 -0.004901 11.00000 -1.50000 H01E 2 1.542428 0.716896 -0.039847 11.00000 -1.50000 H01F 2 1.361412 0.636159 -0.015148 11.00000 -1.50000 AFIX 0 C015 1 1.724958 0.739556 0.133394 11.00000 0.03195 0.04690 = 0.07156 0.01574 0.01590 0.01515 AFIX 137 H01G 2 1.745560 0.667845 0.134114 11.00000 -1.50000 H01H 2 1.753750 0.779745 0.194791 11.00000 -1.50000 H01I 2 1.798124 0.783858 0.091705 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM AG104_a.res in P-1 REM R1 = 0.0437 for 3527 Fo > 4sig(Fo) and 0.0796 for all 5255 data REM 374 parameters refined using 0 restraints END WGHT 0.0488 0.3717 REM Highest difference peak 0.398, deepest hole -0.195, 1-sigma level 0.043 Q1 1 1.1503 0.4139 0.0189 11.00000 0.05 0.40 Q2 1 -0.0451 -0.1626 0.5974 11.00000 0.05 0.24 Q3 1 0.1090 -0.1155 0.5811 11.00000 0.05 0.19 Q4 1 0.5016 0.1466 0.6417 11.00000 0.05 0.19 Q5 1 0.2656 0.0820 0.6853 11.00000 0.05 0.18 Q6 1 0.6968 0.3122 0.5816 11.00000 0.05 0.18 Q7 1 0.1920 -0.0053 0.5419 11.00000 0.05 0.17 Q8 1 0.6681 0.2649 0.4291 11.00000 0.05 0.17 Q9 1 0.1683 -0.0061 0.6353 11.00000 0.05 0.16 Q10 1 0.6739 0.3431 0.5694 11.00000 0.05 0.16 ; _shelx_res_checksum 5103 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 O001 O 0.46259(15) 0.14150(10) 0.43989(8) 0.0250(3) Uani 1 1 d . . O002 O 1.61414(17) 0.90732(11) 0.06346(9) 0.0386(4) Uani 1 1 d . . O007 O 0.9301(2) 0.45620(15) 0.11314(10) 0.0697(6) Uani 1 1 d . . N003 N 0.48707(19) 0.17335(13) 0.59234(10) 0.0282(4) Uani 1 1 d . . N004 N 0.61530(19) 0.26260(13) 0.55893(11) 0.0291(4) Uani 1 1 d . . N005 N 1.1230(2) 0.57881(13) 0.22257(11) 0.0347(4) Uani 1 1 d . . H005 H 1.1557 0.5963 0.2811 0.042 Uiso 1 1 calc R U N006 N 1.50282(19) 0.83257(12) 0.10391(10) 0.0274(4) Uani 1 1 d . . C008 C 0.4003(2) 0.10455(15) 0.52031(12) 0.0234(4) Uani 1 1 d . . C009 C 0.5955(2) 0.23997(14) 0.46969(13) 0.0237(4) Uani 1 1 d . . C00N C 0.2173(2) -0.00072(16) 0.68056(13) 0.0295(4) Uani 1 1 d . . H00N H 0.3136 0.0656 0.6944 0.035 Uiso 1 1 calc R U C00Z C 0.9067(2) 0.47152(16) 0.36077(13) 0.0320(5) Uani 1 1 d . . H00Z H 0.9873 0.5438 0.3790 0.038 Uiso 1 1 calc R U C00Q C 0.9801(3) 0.48798(16) 0.19464(13) 0.0327(5) Uani 1 1 d . . C00S C -0.2994(3) -0.35451(17) 0.69704(15) 0.0381(5) Uani 1 1 d . . H00S H -0.3932 -0.4225 0.6855 0.046 Uiso 1 1 calc R U C00W C 0.7596(2) 0.31943(16) 0.24290(13) 0.0321(5) Uani 1 1 d . . H00W H 0.7404 0.2884 0.1810 0.039 Uiso 1 1 calc R U C00U C 1.4153(2) 0.64725(16) 0.16693(14) 0.0330(5) Uani 1 1 d . . H00A H 1.4133 0.5692 0.1543 0.040 Uiso 1 1 calc R U H00B H 1.4686 0.6745 0.2303 0.040 Uiso 1 1 calc R U C00V C -0.2752(2) -0.35175(16) 0.52852(15) 0.0357(5) Uani 1 1 d . . H00V H -0.3719 -0.4181 0.5155 0.043 Uiso 1 1 calc R U C00T C -0.1937(2) -0.30292(16) 0.45809(14) 0.0330(5) Uani 1 1 d . . H00T H -0.2364 -0.3352 0.3974 0.040 Uiso 1 1 calc R U C00P C 0.8123(2) 0.41099(16) 0.42570(13) 0.0307(4) Uani 1 1 d . . H00P H 0.8296 0.4427 0.4873 0.037 Uiso 1 1 calc R U C00X C 1.2227(3) 0.83079(17) 0.01771(13) 0.0356(5) Uani 1 1 d . . H00C H 1.1186 0.8527 0.0229 0.053 Uiso 1 1 calc R U H00D H 1.1883 0.7517 -0.0054 0.053 Uiso 1 1 calc R U H00E H 1.2945 0.8753 -0.0243 0.053 Uiso 1 1 calc R U C00R C 1.2260(2) 0.64957(15) 0.15855(13) 0.0301(4) Uani 1 1 d . . H00R H 1.1710 0.6209 0.0949 0.036 Uiso 1 1 calc R U C00B C -0.0424(2) -0.20235(14) 0.47460(13) 0.0249(4) Uani 1 1 d . . C00F C 1.3286(2) 0.85089(15) 0.11302(12) 0.0263(4) Uani 1 1 d . . C00G C 0.0467(2) -0.15257(15) 0.40231(13) 0.0277(4) Uani 1 1 d . . H00G H 0.0088 -0.1860 0.3415 0.033 Uiso 1 1 calc R U C00M C -0.0171(2) -0.15148(16) 0.73382(13) 0.0289(4) Uani 1 1 d . . C00O C 0.6645(2) 0.25849(15) 0.30771(13) 0.0300(4) Uani 1 1 d . . H00O H 0.5818 0.1870 0.2893 0.036 Uiso 1 1 calc R U C00D C 0.2508(2) -0.00149(14) 0.50990(12) 0.0231(4) Uani 1 1 d . . C00L C 0.1897(2) -0.05468(15) 0.42001(13) 0.0261(4) Uani 1 1 d . . H00L H 0.2473 -0.0231 0.3707 0.031 Uiso 1 1 calc R U C00E C 0.1655(2) -0.04926(14) 0.58555(12) 0.0228(4) Uani 1 1 d . . C00C C -0.0720(2) -0.20186(15) 0.64150(13) 0.0260(4) Uani 1 1 d . . C00K C 1.2299(2) 0.77099(16) 0.17942(12) 0.0283(4) Uani 1 1 d . . H00F H 1.2858 0.7992 0.2422 0.034 Uiso 1 1 calc R U H00H H 1.1089 0.7723 0.1769 0.034 Uiso 1 1 calc R U C00I C -0.2175(2) -0.30448(15) 0.62277(14) 0.0299(4) Uani 1 1 d . . C00H C 0.6922(2) 0.30361(14) 0.39993(12) 0.0234(4) Uani 1 1 d . . C00J C 0.0179(2) -0.15089(14) 0.56701(12) 0.0235(4) Uani 1 1 d . . C00A C 0.8829(2) 0.42608(15) 0.26890(13) 0.0270(4) Uani 1 1 d . . C00Y C -0.1051(3) -0.20387(17) 0.80561(14) 0.0382(5) Uani 1 1 d . . H00Y H -0.0700 -0.1702 0.8666 0.046 Uiso 1 1 calc R U C010 C 1.5305(2) 0.71928(15) 0.10098(14) 0.0318(5) Uani 1 1 d . . C011 C 0.1301(3) -0.04876(17) 0.75036(13) 0.0342(5) Uani 1 1 d . . H011 H 0.1668 -0.0140 0.8109 0.041 Uiso 1 1 calc R U C012 C 1.3669(3) 0.97383(16) 0.15365(14) 0.0382(5) Uani 1 1 d . . H01A H 1.2578 0.9860 0.1665 0.057 Uiso 1 1 calc R U H01B H 1.4218 1.0237 0.1099 0.057 Uiso 1 1 calc R U H01C H 1.4452 0.9892 0.2101 0.057 Uiso 1 1 calc R U C013 C -0.2436(3) -0.30503(18) 0.78718(16) 0.0415(5) Uani 1 1 d . . H013 H -0.2995 -0.3399 0.8358 0.050 Uiso 1 1 calc R U C014 C 1.4876(3) 0.66277(18) 0.00101(14) 0.0458(6) Uani 1 1 d . . H01D H 1.5320 0.5997 -0.0049 0.069 Uiso 1 1 calc R U H01E H 1.5424 0.7169 -0.0398 0.069 Uiso 1 1 calc R U H01F H 1.3614 0.6362 -0.0151 0.069 Uiso 1 1 calc R U C015 C 1.7250(3) 0.73956(19) 0.13339(17) 0.0485(6) Uani 1 1 d . . H01G H 1.7456 0.6678 0.1341 0.073 Uiso 1 1 calc R U H01H H 1.7537 0.7797 0.1948 0.073 Uiso 1 1 calc R U H01I H 1.7981 0.7839 0.0917 0.073 Uiso 1 1 calc R U 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 0.0219(6) 0.0228(7) 0.0291(7) 0.0087(5) 0.0062(5) 0.0035(5) O002 0.0304(7) 0.0319(8) 0.0461(9) 0.0128(6) 0.0123(6) -0.0046(6) O007 0.0735(12) 0.0655(11) 0.0290(9) 0.0078(8) 0.0044(8) -0.0360(9) N003 0.0210(8) 0.0281(9) 0.0314(9) 0.0084(7) 0.0041(7) 0.0003(7) N004 0.0234(8) 0.0286(9) 0.0327(9) 0.0098(7) 0.0055(7) 0.0026(7) N005 0.0330(9) 0.0349(9) 0.0263(9) 0.0106(7) 0.0043(7) -0.0050(7) N006 0.0235(8) 0.0232(8) 0.0296(9) 0.0060(7) 0.0055(7) -0.0021(7) C008 0.0193(9) 0.0261(10) 0.0267(10) 0.0104(8) 0.0060(8) 0.0072(8) C009 0.0180(9) 0.0212(9) 0.0317(11) 0.0080(8) 0.0035(8) 0.0045(7) C00N 0.0253(10) 0.0285(10) 0.0295(11) 0.0058(8) 0.0010(8) 0.0010(8) C00Z 0.0292(10) 0.0237(10) 0.0356(11) 0.0061(8) 0.0047(9) -0.0030(8) C00Q 0.0312(11) 0.0299(11) 0.0307(12) 0.0092(9) 0.0054(9) -0.0011(9) C00S 0.0265(11) 0.0300(11) 0.0593(15) 0.0149(10) 0.0158(10) 0.0061(9) C00W 0.0326(11) 0.0289(11) 0.0283(10) 0.0031(8) 0.0055(8) 0.0006(9) C00U 0.0333(11) 0.0270(10) 0.0383(12) 0.0090(9) 0.0086(9) 0.0065(9) C00V 0.0222(10) 0.0245(10) 0.0550(14) 0.0043(9) 0.0028(9) 0.0001(8) C00T 0.0252(10) 0.0280(11) 0.0407(12) -0.0016(9) -0.0024(9) 0.0043(8) C00P 0.0298(10) 0.0291(11) 0.0282(10) 0.0038(8) 0.0046(8) 0.0022(8) C00X 0.0336(11) 0.0396(12) 0.0296(11) 0.0105(9) 0.0011(9) 0.0053(9) C00R 0.0288(10) 0.0296(10) 0.0261(10) 0.0097(8) 0.0068(8) -0.0016(8) C00B 0.0198(9) 0.0209(9) 0.0347(11) 0.0040(8) 0.0013(8) 0.0076(7) C00F 0.0224(9) 0.0262(10) 0.0276(10) 0.0054(8) 0.0033(8) 0.0032(8) C00G 0.0282(10) 0.0281(10) 0.0267(10) -0.0003(8) 0.0011(8) 0.0104(8) C00M 0.0258(10) 0.0319(10) 0.0316(11) 0.0107(8) 0.0076(8) 0.0100(8) C00O 0.0292(10) 0.0226(10) 0.0325(11) 0.0044(8) 0.0063(8) -0.0008(8) C00D 0.0193(9) 0.0227(9) 0.0289(10) 0.0070(8) 0.0031(7) 0.0081(7) C00L 0.0259(10) 0.0276(10) 0.0275(10) 0.0081(8) 0.0082(8) 0.0100(8) C00E 0.0186(9) 0.0232(9) 0.0284(10) 0.0053(8) 0.0022(7) 0.0086(7) C00C 0.0192(9) 0.0254(10) 0.0366(11) 0.0090(8) 0.0065(8) 0.0093(8) C00K 0.0208(9) 0.0359(11) 0.0261(10) 0.0078(8) 0.0040(8) 0.0049(8) C00I 0.0195(9) 0.0259(10) 0.0457(12) 0.0087(9) 0.0070(9) 0.0075(8) C00H 0.0184(9) 0.0224(9) 0.0306(10) 0.0081(8) 0.0033(7) 0.0067(7) C00J 0.0181(9) 0.0229(9) 0.0319(10) 0.0077(8) 0.0042(7) 0.0085(7) C00A 0.0237(10) 0.0257(10) 0.0320(11) 0.0102(8) 0.0062(8) 0.0062(8) C00Y 0.0419(12) 0.0421(13) 0.0330(12) 0.0120(9) 0.0140(9) 0.0127(10) C010 0.0287(10) 0.0253(10) 0.0406(12) 0.0053(9) 0.0097(9) 0.0058(8) C011 0.0342(11) 0.0372(12) 0.0273(11) 0.0052(9) 0.0041(9) 0.0053(9) C012 0.0397(12) 0.0311(11) 0.0435(13) 0.0054(9) 0.0055(10) 0.0105(9) C013 0.0383(12) 0.0416(13) 0.0497(14) 0.0198(11) 0.0236(10) 0.0122(10) C014 0.0546(14) 0.0354(12) 0.0460(13) 0.0016(10) 0.0244(11) 0.0089(11) C015 0.0320(12) 0.0469(14) 0.0716(17) 0.0157(12) 0.0159(11) 0.0151(10) 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 C009 O001 C008 103.23(13) C008 N003 N004 106.52(14) C009 N004 N003 106.21(14) C00Q N005 C00R 123.14(16) C00Q N005 H005 118.4 C00R N005 H005 118.4 O002 N006 C00F 115.54(14) O002 N006 C010 115.17(14) C00F N006 C010 124.42(14) N003 C008 O001 111.69(15) N003 C008 C00D 132.42(16) O001 C008 C00D 115.88(15) N004 C009 O001 112.34(15) N004 C009 C00H 129.80(16) O001 C009 C00H 117.85(16) C011 C00N C00E 121.80(17) C011 C00N H00N 119.1 C00E C00N H00N 119.1 C00P C00Z C00A 120.72(17) C00P C00Z H00Z 119.6 C00A C00Z H00Z 119.6 O007 C00Q N005 121.98(17) O007 C00Q C00A 120.92(17) N005 C00Q C00A 117.10(17) C013 C00S C00I 121.17(19) C013 C00S H00S 119.4 C00I C00S H00S 119.4 C00O C00W C00A 120.81(18) C00O C00W H00W 119.6 C00A C00W H00W 119.6 C00R C00U C010 113.42(15) C00R C00U H00A 108.9 C010 C00U H00A 108.9 C00R C00U H00B 108.9 C010 C00U H00B 108.9 H00A C00U H00B 107.7 C00T C00V C00I 121.65(18) C00T C00V H00V 119.2 C00I C00V H00V 119.2 C00V C00T C00B 121.26(18) C00V C00T H00T 119.4 C00B C00T H00T 119.4 C00Z C00P C00H 120.47(18) C00Z C00P H00P 119.8 C00H C00P H00P 119.8 C00F C00X H00C 109.5 C00F C00X H00D 109.5 H00C C00X H00D 109.5 C00F C00X H00E 109.5 H00C C00X H00E 109.5 H00D C00X H00E 109.5 N005 C00R C00K 110.18(15) N005 C00R C00U 110.69(15) C00K C00R C00U 108.61(15) N005 C00R H00R 109.1 C00K C00R H00R 109.1 C00U C00R H00R 109.1 C00G C00B C00J 118.96(16) C00G C00B C00T 121.87(17) C00J C00B C00T 119.16(17) N006 C00F C012 107.54(14) N006 C00F C00X 109.97(15) C012 C00F C00X 109.27(16) N006 C00F C00K 108.43(14) C012 C00F C00K 109.71(15) C00X C00F C00K 111.82(15) C00L C00G C00B 120.66(17) C00L C00G H00G 119.7 C00B C00G H00G 119.7 C00Y C00M C00C 119.47(18) C00Y C00M C011 122.40(18) C00C C00M C011 118.12(16) C00W C00O C00H 120.11(17) C00W C00O H00O 119.9 C00H C00O H00O 119.9 C00L C00D C00E 119.69(16) C00L C00D C008 117.02(16) C00E C00D C008 123.28(16) C00G C00L C00D 121.70(17) C00G C00L H00L 119.2 C00D C00L H00L 119.2 C00D C00E C00J 118.47(16) C00D C00E C00N 124.00(16) C00J C00E C00N 117.53(16) C00M C00C C00I 119.49(17) C00M C00C C00J 120.51(16) C00I C00C C00J 120.00(17) C00R C00K C00F 113.99(15) C00R C00K H00F 108.8 C00F C00K H00F 108.8 C00R C00K H00H 108.8 C00F C00K H00H 108.8 H00F C00K H00H 107.6 C00S C00I C00C 118.87(19) C00S C00I C00V 122.55(18) C00C C00I C00V 118.58(17) C00P C00H C00O 119.20(17) C00P C00H C009 119.80(17) C00O C00H C009 121.00(16) C00B C00J C00E 120.51(16) C00B C00J C00C 119.27(16) C00E C00J C00C 120.21(16) C00Z C00A C00W 118.66(17) C00Z C00A C00Q 123.36(17) C00W C00A C00Q 117.95(17) C013 C00Y C00M 120.8(2) C013 C00Y H00Y 119.6 C00M C00Y H00Y 119.6 N006 C010 C015 107.75(15) N006 C010 C014 108.59(16) C015 C010 C014 109.59(17) N006 C010 C00U 109.67(15) C015 C010 C00U 109.03(16) C014 C010 C00U 112.10(16) C00N C011 C00M 121.81(18) C00N C011 H011 119.1 C00M C011 H011 119.1 C00F C012 H01A 109.5 C00F C012 H01B 109.5 H01A C012 H01B 109.5 C00F C012 H01C 109.5 H01A C012 H01C 109.5 H01B C012 H01C 109.5 C00S C013 C00Y 120.20(19) C00S C013 H013 119.9 C00Y C013 H013 119.9 C010 C014 H01D 109.5 C010 C014 H01E 109.5 H01D C014 H01E 109.5 C010 C014 H01F 109.5 H01D C014 H01F 109.5 H01E C014 H01F 109.5 C010 C015 H01G 109.5 C010 C015 H01H 109.5 H01G C015 H01H 109.5 C010 C015 H01I 109.5 H01G C015 H01I 109.5 H01H C015 H01I 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O001 C009 1.357(2) O001 C008 1.365(2) O002 N006 1.2869(18) O007 C00Q 1.212(2) N003 C008 1.295(2) N003 N004 1.405(2) N004 C009 1.291(2) N005 C00Q 1.337(2) N005 C00R 1.456(2) N005 H005 0.8600 N006 C00F 1.494(2) N006 C010 1.495(2) C008 C00D 1.464(2) C009 C00H 1.458(2) C00N C011 1.350(3) C00N C00E 1.435(2) C00N H00N 0.9300 C00Z C00P 1.379(3) C00Z C00A 1.381(3) C00Z H00Z 0.9300 C00Q C00A 1.502(2) C00S C013 1.378(3) C00S C00I 1.396(3) C00S H00S 0.9300 C00W C00O 1.382(2) C00W C00A 1.384(3) C00W H00W 0.9300 C00U C00R 1.518(3) C00U C010 1.528(2) C00U H00A 0.9700 C00U H00B 0.9700 C00V C00T 1.342(3) C00V C00I 1.426(3) C00V H00V 0.9300 C00T C00B 1.429(2) C00T H00T 0.9300 C00P C00H 1.380(2) C00P H00P 0.9300 C00X C00F 1.526(3) C00X H00C 0.9600 C00X H00D 0.9600 C00X H00E 0.9600 C00R C00K 1.509(3) C00R H00R 0.9800 C00B C00G 1.394(2) C00B C00J 1.418(3) C00F C012 1.523(3) C00F C00K 1.526(2) C00G C00L 1.373(2) C00G H00G 0.9300 C00M C00Y 1.396(3) C00M C00C 1.408(3) C00M C011 1.427(3) C00O C00H 1.383(3) C00O H00O 0.9300 C00D C00L 1.392(2) C00D C00E 1.414(2) C00L H00L 0.9300 C00E C00J 1.422(2) C00C C00I 1.421(2) C00C C00J 1.428(2) C00K H00F 0.9700 C00K H00H 0.9700 C00Y C013 1.381(3) C00Y H00Y 0.9300 C010 C015 1.523(3) C010 C014 1.525(3) C011 H011 0.9300 C012 H01A 0.9600 C012 H01B 0.9600 C012 H01C 0.9600 C013 H013 0.9300 C014 H01D 0.9600 C014 H01E 0.9600 C014 H01F 0.9600 C015 H01G 0.9600 C015 H01H 0.9600 C015 H01I 0.9600