#------------------------------------------------------------------------------ #$Date: 2020-03-05 02:31:18 +0200 (Thu, 05 Mar 2020) $ #$Revision: 249050 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557297.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_1557297 loop_ _publ_author_name 'Warghude, Prakash K.' 'Sabale, Abhijeet S.' 'Bhat, Ramakrishna G.' _publ_section_title ; Access to highly enantioselective and diastereoselective spirooxindole dihydrofuran fused pyrazolones. ; _journal_issue 9 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 1794 _journal_paper_doi 10.1039/d0ob00007h _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety C23H19N3O5 _chemical_formula_sum 'C23 H19 N3 O5' _chemical_formula_weight 417.41 _chemical_melting_point 401 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-11-24 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 115.450(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.2231(13) _cell_length_b 8.1552(9) _cell_length_c 11.9835(14) _cell_measurement_reflns_used 9399 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 65.20 _cell_measurement_theta_min 4.09 _cell_volume 990.4(2) _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 0.989 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'Omega and phi scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_unetI/netI 0.0421 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 23332 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 78.820 _diffrn_reflns_theta_min 4.085 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.832 _exptl_absorpt_correction_T_max 0.7541 _exptl_absorpt_correction_T_min 0.6329 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 436 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Chloroform and Hexane' _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.212 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.03(11) _refine_ls_extinction_coef 0.0182(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 4111 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0368 _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^)+(0.0331P)^2^+0.4564P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.0954 _reflns_Friedel_coverage 0.836 _reflns_Friedel_fraction_full 0.987 _reflns_Friedel_fraction_max 0.943 _reflns_number_gt 3820 _reflns_number_total 4111 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00007h2.cif _cod_data_source_block T1_a _cod_depositor_comments 'Adding full bibliography for 1557297.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 1557297 _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_res_file ; T1_a.res created by SHELXL-2014/7 TITL T1_a.res in P2(1) REM Old TITL T1 in P2(1) REM SHELXT solution in P2(1) REM R1 0.080, Rweak 0.026, Alpha 0.001, Orientation as input REM Flack x = 0.001 ( 0.102 ) from Parsons' quotients REM Formula found by SHELXT: C24 N2 O5 CELL 1.54178 11.2231 8.1552 11.9835 90.000 115.450 90.000 ZERR 2.000 0.0013 0.0009 0.0014 0.000 0.005 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N O UNIT 46 38 6 10 ACTA TEMP -173.000 L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 20 WGHT 0.033100 0.456400 EXTI 0.018164 FVAR 1.39866 O001 4 0.356676 0.733665 0.132711 11.00000 0.02539 0.01858 = 0.02891 0.00459 0.01431 0.00073 N1 3 0.225427 0.532033 0.159224 11.00000 0.02133 0.01707 = 0.02658 0.00116 0.01168 -0.00030 O002 4 0.435128 0.432595 0.035839 11.00000 0.02675 0.02785 = 0.01867 0.00028 0.01230 0.00379 O003 4 0.531703 0.192226 0.372005 11.00000 0.03181 0.01728 = 0.02914 0.00329 0.01295 -0.00053 O004 4 0.815261 0.300676 0.372670 11.00000 0.02328 0.03446 = 0.02871 0.00228 0.00775 0.00301 O005 4 0.817855 0.219440 0.193986 11.00000 0.03444 0.03815 = 0.04570 -0.00174 0.02387 0.00908 N006 3 0.605180 0.438337 0.469989 11.00000 0.02536 0.02192 = 0.01825 0.00038 0.00853 0.00062 N007 3 0.218084 0.357789 0.154693 11.00000 0.02552 0.01542 = 0.02548 -0.00050 0.01025 -0.00272 C009 1 0.639801 0.592536 0.440513 11.00000 0.01889 0.02185 = 0.02147 0.00004 0.00827 0.00250 C00A 1 0.614189 0.596760 0.316300 11.00000 0.01904 0.01657 = 0.02271 -0.00115 0.00886 0.00030 C00B 1 0.556945 0.364986 0.069880 11.00000 0.02524 0.02129 = 0.02904 -0.00157 0.01418 0.00163 AFIX 43 H00B 2 0.588041 0.329616 0.011587 11.00000 -1.20000 AFIX 0 C00C 1 0.319514 0.303612 0.142754 11.00000 0.02446 0.01898 = 0.01796 -0.00026 0.00599 -0.00092 C00D 1 0.412860 0.439051 0.146096 11.00000 0.02535 0.01798 = 0.01719 0.00143 0.01065 0.00060 C00E 1 0.560384 0.336007 0.371259 11.00000 0.02131 0.01905 = 0.02058 0.00135 0.01016 0.00301 C00F 1 0.629190 0.352503 0.192194 11.00000 0.02510 0.01732 = 0.02455 -0.00130 0.01383 0.00018 C00G 1 0.643762 0.735234 0.266734 11.00000 0.02187 0.02035 = 0.02738 0.00130 0.01082 0.00060 AFIX 43 H00G 2 0.629474 0.737521 0.182650 11.00000 -1.20000 AFIX 0 C00H 1 0.331234 0.591335 0.143720 11.00000 0.02231 0.01921 = 0.01684 0.00223 0.00869 0.00195 C00I 1 0.555223 0.433922 0.258030 11.00000 0.02376 0.01619 = 0.02176 -0.00015 0.01206 0.00253 C00J 1 0.118753 0.621871 0.163824 11.00000 0.02002 0.01969 = 0.01978 -0.00205 0.00683 -0.00079 C00K 1 0.693613 0.725213 0.518103 11.00000 0.02497 0.02769 = 0.02561 -0.00606 0.00934 0.00069 AFIX 43 H00K 2 0.712729 0.720433 0.603338 11.00000 -1.20000 AFIX 0 C00L 1 0.694851 0.871197 0.342340 11.00000 0.02410 0.01998 = 0.03872 0.00051 0.01446 0.00003 AFIX 43 H00L 2 0.713663 0.968307 0.309118 11.00000 -1.20000 AFIX 0 C00M 1 0.762693 0.283442 0.248866 11.00000 0.02402 0.01916 = 0.03149 0.00136 0.01425 -0.00130 C00N 1 -0.003696 0.872556 0.132803 11.00000 0.02282 0.02400 = 0.03050 0.00107 0.00682 0.00192 AFIX 43 H00N 2 -0.019044 0.982967 0.104940 11.00000 -1.20000 AFIX 0 C00O 1 0.094137 0.782372 0.120009 11.00000 0.02063 0.02431 = 0.02804 0.00286 0.01011 0.00005 AFIX 43 H00O 2 0.144315 0.829718 0.081503 11.00000 -1.20000 AFIX 0 C00P 1 -0.079349 0.802665 0.186023 11.00000 0.02564 0.03282 = 0.03492 -0.00447 0.01450 0.00403 AFIX 43 H00P 2 -0.145192 0.865419 0.196407 11.00000 -1.20000 AFIX 0 C00Q 1 0.040506 0.548832 0.213411 11.00000 0.02988 0.02341 = 0.03327 0.00146 0.01757 0.00029 AFIX 43 H00Q 2 0.054432 0.437711 0.239687 11.00000 -1.20000 AFIX 0 C00R 1 -0.058222 0.640288 0.224052 11.00000 0.03023 0.03625 = 0.03912 0.00071 0.02179 -0.00166 AFIX 43 H00R 2 -0.112167 0.591081 0.257859 11.00000 -1.20000 AFIX 0 C00S 1 0.718563 0.866357 0.465618 11.00000 0.02590 0.02430 = 0.03319 -0.00988 0.01124 -0.00249 AFIX 43 H00S 2 0.752500 0.960986 0.515523 11.00000 -1.20000 AFIX 0 C00T 1 0.638076 0.382783 0.595687 11.00000 0.03448 0.03165 = 0.01903 0.00347 0.01006 0.00267 AFIX 137 H00A 2 0.618453 0.265542 0.594610 11.00000 -1.50000 H00C 2 0.585690 0.444232 0.629160 11.00000 -1.50000 H00D 2 0.732162 0.401293 0.647643 11.00000 -1.50000 AFIX 0 C00U 1 0.330179 0.128390 0.113658 11.00000 0.03133 0.02172 = 0.03208 -0.00325 0.00954 -0.00089 AFIX 137 H00E 2 0.418351 0.087311 0.167759 11.00000 -1.50000 H00F 2 0.315613 0.118461 0.027233 11.00000 -1.50000 H00H 2 0.263597 0.063986 0.126818 11.00000 -1.50000 AFIX 0 C00V 1 0.947475 0.235951 0.439012 11.00000 0.02280 0.05073 = 0.04621 0.00765 0.00649 0.00419 AFIX 137 H00I 2 0.977411 0.254080 0.527837 11.00000 -1.50000 H00J 2 1.007248 0.291860 0.411251 11.00000 -1.50000 H00M 2 0.947206 0.118128 0.422828 11.00000 -1.50000 REM ##### AFIX 0 HKLF 4 REM T1_a.res in P2(1) REM R1 = 0.0368 for 3820 Fo > 4sig(Fo) and 0.0421 for all 4111 data REM 284 parameters refined using 1 restraints END WGHT 0.0331 0.4564 REM Highest difference peak 0.212, deepest hole -0.208, 1-sigma level 0.045 Q1 1 0.4937 0.4284 0.2188 11.00000 0.05 0.21 Q2 1 0.3753 0.3573 0.1482 11.00000 0.05 0.19 Q3 1 0.5526 0.3647 -0.0350 11.00000 0.05 0.19 Q4 1 0.5904 0.6786 0.2837 11.00000 0.05 0.19 Q5 1 0.5756 0.5001 0.2788 11.00000 0.05 0.18 Q6 1 0.4048 0.3316 -0.0271 11.00000 0.05 0.18 Q7 1 0.5924 0.3978 0.2414 11.00000 0.05 0.18 Q8 1 0.7382 0.0972 0.6434 11.00000 0.05 0.17 Q9 1 0.5721 0.2795 0.1220 11.00000 0.05 0.17 Q10 1 0.5607 0.6428 0.1030 11.00000 0.05 0.17 Q11 1 0.4748 0.1785 0.1653 11.00000 0.05 0.17 Q12 1 0.7261 1.0226 0.4818 11.00000 0.05 0.17 Q13 1 0.7214 0.6233 0.3377 11.00000 0.05 0.17 Q14 1 0.5339 0.3732 0.2996 11.00000 0.05 0.16 Q15 1 0.5132 0.2846 0.1831 11.00000 0.05 0.16 Q16 1 0.4385 0.3065 0.0633 11.00000 0.05 0.16 Q17 1 0.0816 0.6886 0.1098 11.00000 0.05 0.16 Q18 1 0.2665 0.0996 0.0525 11.00000 0.05 0.16 Q19 1 0.5122 0.3823 0.1686 11.00000 0.05 0.16 Q20 1 0.1731 0.5989 0.0797 11.00000 0.05 0.15 ; _shelx_res_checksum 36607 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 O001 O 0.35668(19) 0.7337(2) 0.13271(18) 0.0234(4) Uani 1 1 d . . N1 N 0.2254(2) 0.5320(3) 0.1592(2) 0.0212(5) Uani 1 1 d . . O002 O 0.43513(19) 0.4326(3) 0.03584(17) 0.0235(4) Uani 1 1 d . . O003 O 0.5317(2) 0.1922(2) 0.37201(19) 0.0261(5) Uani 1 1 d . . O004 O 0.8153(2) 0.3007(3) 0.3727(2) 0.0300(5) Uani 1 1 d . . O005 O 0.8179(2) 0.2194(3) 0.1940(2) 0.0371(6) Uani 1 1 d . . N006 N 0.6052(2) 0.4383(3) 0.4700(2) 0.0221(5) Uani 1 1 d . . N007 N 0.2181(2) 0.3578(3) 0.1547(2) 0.0224(5) Uani 1 1 d . . C009 C 0.6398(3) 0.5925(3) 0.4405(3) 0.0209(6) Uani 1 1 d . . C00A C 0.6142(3) 0.5968(3) 0.3163(3) 0.0195(6) Uani 1 1 d . . C00B C 0.5569(3) 0.3650(4) 0.0699(3) 0.0243(6) Uani 1 1 d . . H00B H 0.5880 0.3296 0.0116 0.029 Uiso 1 1 calc R U C00C C 0.3195(3) 0.3036(3) 0.1428(3) 0.0216(6) Uani 1 1 d . . C00D C 0.4129(3) 0.4391(4) 0.1461(2) 0.0196(5) Uani 1 1 d . . C00E C 0.5604(3) 0.3360(3) 0.3713(3) 0.0199(6) Uani 1 1 d . . C00F C 0.6292(3) 0.3525(3) 0.1922(3) 0.0212(6) Uani 1 1 d . . C00G C 0.6438(3) 0.7352(3) 0.2667(3) 0.0231(6) Uani 1 1 d . . H00G H 0.6295 0.7375 0.1827 0.028 Uiso 1 1 calc R U C00H C 0.3312(3) 0.5913(3) 0.1437(2) 0.0194(6) Uani 1 1 d . . C00I C 0.5552(3) 0.4339(4) 0.2580(2) 0.0198(5) Uani 1 1 d . . C00J C 0.1188(3) 0.6219(3) 0.1638(3) 0.0204(6) Uani 1 1 d . . C00K C 0.6936(3) 0.7252(4) 0.5181(3) 0.0266(6) Uani 1 1 d . . H00K H 0.7127 0.7204 0.6033 0.032 Uiso 1 1 calc R U C00L C 0.6949(3) 0.8712(4) 0.3423(3) 0.0273(6) Uani 1 1 d . . H00L H 0.7137 0.9683 0.3091 0.033 Uiso 1 1 calc R U C00M C 0.7627(3) 0.2834(3) 0.2489(3) 0.0241(6) Uani 1 1 d . . C00N C -0.0037(3) 0.8726(4) 0.1328(3) 0.0274(6) Uani 1 1 d . . H00N H -0.0190 0.9830 0.1049 0.033 Uiso 1 1 calc R U C00O C 0.0941(3) 0.7824(4) 0.1200(3) 0.0244(6) Uani 1 1 d . . H00O H 0.1443 0.8297 0.0815 0.029 Uiso 1 1 calc R U C00P C -0.0793(3) 0.8027(4) 0.1860(3) 0.0306(7) Uani 1 1 d . . H00P H -0.1452 0.8654 0.1964 0.037 Uiso 1 1 calc R U C00Q C 0.0405(3) 0.5488(4) 0.2134(3) 0.0275(6) Uani 1 1 d . . H00Q H 0.0544 0.4377 0.2397 0.033 Uiso 1 1 calc R U C00R C -0.0582(3) 0.6403(4) 0.2241(3) 0.0328(7) Uani 1 1 d . . H00R H -0.1122 0.5911 0.2579 0.039 Uiso 1 1 calc R U C00S C 0.7186(3) 0.8664(4) 0.4656(3) 0.0283(7) Uani 1 1 d . . H00S H 0.7525 0.9610 0.5155 0.034 Uiso 1 1 calc R U C00T C 0.6381(3) 0.3828(4) 0.5957(3) 0.0289(7) Uani 1 1 d . . H00A H 0.6185 0.2655 0.5946 0.043 Uiso 1 1 calc R U H00C H 0.5857 0.4442 0.6292 0.043 Uiso 1 1 calc R U H00D H 0.7322 0.4013 0.6476 0.043 Uiso 1 1 calc R U C00U C 0.3302(3) 0.1284(4) 0.1137(3) 0.0298(7) Uani 1 1 d . . H00E H 0.4184 0.0873 0.1678 0.045 Uiso 1 1 calc R U H00F H 0.3156 0.1185 0.0272 0.045 Uiso 1 1 calc R U H00H H 0.2636 0.0640 0.1268 0.045 Uiso 1 1 calc R U C00V C 0.9475(3) 0.2360(5) 0.4390(3) 0.0428(9) Uani 1 1 d . . H00I H 0.9774 0.2541 0.5278 0.064 Uiso 1 1 calc R U H00J H 1.0072 0.2919 0.4113 0.064 Uiso 1 1 calc R U H00M H 0.9472 0.1181 0.4228 0.064 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 0.0254(10) 0.0186(9) 0.0289(11) 0.0046(8) 0.0143(9) 0.0007(8) N1 0.0213(12) 0.0171(11) 0.0266(12) 0.0012(9) 0.0117(10) -0.0003(9) O002 0.0268(10) 0.0278(10) 0.0187(9) 0.0003(8) 0.0123(8) 0.0038(9) O003 0.0318(11) 0.0173(10) 0.0291(11) 0.0033(8) 0.0129(9) -0.0005(8) O004 0.0233(10) 0.0345(12) 0.0287(11) 0.0023(9) 0.0078(8) 0.0030(9) O005 0.0344(12) 0.0381(13) 0.0457(14) -0.0017(11) 0.0239(11) 0.0091(10) N006 0.0254(12) 0.0219(11) 0.0183(11) 0.0004(10) 0.0085(9) 0.0006(10) N007 0.0255(12) 0.0154(11) 0.0255(12) -0.0005(10) 0.0103(10) -0.0027(10) C009 0.0189(13) 0.0218(13) 0.0215(13) 0.0000(11) 0.0083(11) 0.0025(10) C00A 0.0190(13) 0.0166(12) 0.0227(14) -0.0011(10) 0.0089(11) 0.0003(10) C00B 0.0252(14) 0.0213(13) 0.0290(15) -0.0016(12) 0.0142(12) 0.0016(12) C00C 0.0245(14) 0.0190(13) 0.0180(13) -0.0003(10) 0.0060(11) -0.0009(11) C00D 0.0254(13) 0.0180(12) 0.0172(12) 0.0014(11) 0.0106(10) 0.0006(12) C00E 0.0213(13) 0.0191(13) 0.0206(13) 0.0014(10) 0.0102(11) 0.0030(10) C00F 0.0251(13) 0.0173(13) 0.0245(14) -0.0013(11) 0.0138(11) 0.0002(11) C00G 0.0219(13) 0.0203(14) 0.0274(15) 0.0013(11) 0.0108(11) 0.0006(11) C00H 0.0223(14) 0.0192(13) 0.0168(13) 0.0022(10) 0.0087(11) 0.0020(11) C00I 0.0238(13) 0.0162(12) 0.0218(13) -0.0002(11) 0.0121(11) 0.0025(11) C00J 0.0200(13) 0.0197(13) 0.0198(13) -0.0021(10) 0.0068(11) -0.0008(10) C00K 0.0250(14) 0.0277(15) 0.0256(15) -0.0061(12) 0.0093(12) 0.0007(12) C00L 0.0241(14) 0.0200(13) 0.0387(17) 0.0005(12) 0.0145(13) 0.0000(12) C00M 0.0240(14) 0.0192(13) 0.0315(15) 0.0014(11) 0.0143(12) -0.0013(11) C00N 0.0228(14) 0.0240(14) 0.0305(15) 0.0011(12) 0.0068(12) 0.0019(11) C00O 0.0206(13) 0.0243(14) 0.0280(15) 0.0029(12) 0.0101(11) 0.0001(11) C00P 0.0256(15) 0.0328(17) 0.0349(17) -0.0045(13) 0.0145(13) 0.0040(13) C00Q 0.0299(15) 0.0234(15) 0.0333(16) 0.0015(12) 0.0176(13) 0.0003(12) C00R 0.0302(16) 0.0362(18) 0.0391(19) 0.0007(14) 0.0218(14) -0.0017(13) C00S 0.0259(14) 0.0243(15) 0.0332(16) -0.0099(13) 0.0112(13) -0.0025(13) C00T 0.0345(16) 0.0317(17) 0.0190(14) 0.0035(12) 0.0101(12) 0.0027(13) C00U 0.0313(16) 0.0217(15) 0.0321(17) -0.0032(12) 0.0095(13) -0.0009(12) C00V 0.0228(16) 0.051(2) 0.046(2) 0.0076(17) 0.0065(15) 0.0042(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C00H N1 C00J 128.1(2) C00H N1 N007 112.8(2) C00J N1 N007 118.6(2) C00B O002 C00D 106.6(2) C00M O004 C00V 115.3(3) C00E N006 C009 111.7(2) C00E N006 C00T 122.9(3) C009 N006 C00T 124.2(2) C00C N007 N1 107.9(2) C00K C009 C00A 122.0(3) C00K C009 N006 128.2(3) C00A C009 N006 109.8(2) C00G C00A C009 120.2(3) C00G C00A C00I 131.1(3) C009 C00A C00I 108.7(2) C00F C00B O002 114.6(2) C00F C00B H00B 122.7 O002 C00B H00B 122.7 N007 C00C C00U 121.4(3) N007 C00C C00D 112.5(2) C00U C00C C00D 125.7(3) O002 C00D C00C 109.8(2) O002 C00D C00H 110.4(2) C00C C00D C00H 100.9(2) O002 C00D C00I 105.4(2) C00C C00D C00I 116.0(2) C00H C00D C00I 114.4(2) O003 C00E N006 125.9(3) O003 C00E C00I 126.2(3) N006 C00E C00I 107.8(2) C00B C00F C00M 123.6(3) C00B C00F C00I 109.0(2) C00M C00F C00I 127.2(2) C00A C00G C00L 118.7(3) C00A C00G H00G 120.7 C00L C00G H00G 120.7 O001 C00H N1 127.6(3) O001 C00H C00D 127.4(3) N1 C00H C00D 104.9(2) C00A C00I C00F 113.2(2) C00A C00I C00E 101.7(2) C00F C00I C00E 113.9(2) C00A C00I C00D 116.7(2) C00F C00I C00D 98.6(2) C00E C00I C00D 113.5(2) C00Q C00J C00O 120.3(3) C00Q C00J N1 119.5(2) C00O C00J N1 120.2(3) C009 C00K C00S 117.1(3) C009 C00K H00K 121.4 C00S C00K H00K 121.4 C00S C00L C00G 120.6(3) C00S C00L H00L 119.7 C00G C00L H00L 119.7 O005 C00M O004 124.3(3) O005 C00M C00F 125.4(3) O004 C00M C00F 110.3(2) C00P C00N C00O 120.3(3) C00P C00N H00N 119.8 C00O C00N H00N 119.8 C00N C00O C00J 119.7(3) C00N C00O H00O 120.1 C00J C00O H00O 120.1 C00N C00P C00R 119.5(3) C00N C00P H00P 120.3 C00R C00P H00P 120.3 C00R C00Q C00J 119.1(3) C00R C00Q H00Q 120.5 C00J C00Q H00Q 120.5 C00Q C00R C00P 120.9(3) C00Q C00R H00R 119.5 C00P C00R H00R 119.5 C00L C00S C00K 121.3(3) C00L C00S H00S 119.3 C00K C00S H00S 119.3 N006 C00T H00A 109.5 N006 C00T H00C 109.5 H00A C00T H00C 109.5 N006 C00T H00D 109.5 H00A C00T H00D 109.5 H00C C00T H00D 109.5 C00C C00U H00E 109.5 C00C C00U H00F 109.5 H00E C00U H00F 109.5 C00C C00U H00H 109.5 H00E C00U H00H 109.5 H00F C00U H00H 109.5 O004 C00V H00I 109.5 O004 C00V H00J 109.5 H00I C00V H00J 109.5 O004 C00V H00M 109.5 H00I C00V H00M 109.5 H00J C00V H00M 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O001 C00H 1.216(3) N1 C00H 1.367(4) N1 C00J 1.425(4) N1 N007 1.423(3) O002 C00B 1.364(3) O002 C00D 1.447(3) O003 C00E 1.217(3) O004 C00M 1.348(4) O004 C00V 1.449(4) O005 C00M 1.199(4) N006 C00E 1.356(4) N006 C009 1.405(4) N006 C00T 1.460(4) N007 C00C 1.285(4) C009 C00K 1.385(4) C009 C00A 1.390(4) C00A C00G 1.381(4) C00A C00I 1.514(4) C00B C00F 1.340(4) C00B H00B 0.9500 C00C C00U 1.488(4) C00C C00D 1.511(4) C00D C00H 1.536(4) C00D C00I 1.585(4) C00E C00I 1.554(4) C00F C00M 1.466(4) C00F C00I 1.522(4) C00G C00L 1.390(4) C00G H00G 0.9500 C00J C00Q 1.388(4) C00J C00O 1.393(4) C00K C00S 1.397(5) C00K H00K 0.9500 C00L C00S 1.385(5) C00L H00L 0.9500 C00N C00P 1.385(5) C00N C00O 1.384(4) C00N H00N 0.9500 C00O H00O 0.9500 C00P C00R 1.387(5) C00P H00P 0.9500 C00Q C00R 1.386(4) C00Q H00Q 0.9500 C00R H00R 0.9500 C00S H00S 0.9500 C00T H00A 0.9800 C00T H00C 0.9800 C00T H00D 0.9800 C00U H00E 0.9800 C00U H00F 0.9800 C00U H00H 0.9800 C00V H00I 0.9800 C00V H00J 0.9800 C00V H00M 0.9800