#------------------------------------------------------------------------------ #$Date: 2019-03-24 04:00:47 +0200 (Sun, 24 Mar 2019) $ #$Revision: 214310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156741.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_7156741 loop_ _publ_author_name 'Jin , Li-Wen' 'Jiang, Fei' 'Chen, Ke-Wei' 'Du, Baixiang' 'Mei, Guang-Jian' 'Shi, Feng' _publ_section_title ; Phosphine-Catalyzed Regiospecific (3+2) Cyclization of 3-Nitroindoles with Allene Esters ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00432G _journal_year 2019 _chemical_formula_moiety 'C21 H18 N2 O5' _chemical_formula_sum 'C21 H18 N2 O5' _chemical_formula_weight 378.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-04-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486) ; _audit_update_record ; 2019-02-20 deposited with the CCDC. 2019-03-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.560(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.7507(18) _cell_length_b 9.3997(11) _cell_length_c 12.8142(15) _cell_measurement_reflns_used 2462 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.16 _cell_measurement_theta_min 2.52 _cell_volume 1893.5(4) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.950 _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 0.0255 _diffrn_reflns_av_unetI/netI 0.0369 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.950 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11052 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.950 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.074 _diffrn_reflns_theta_min 2.525 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0515 before and 0.0405 after correction. The Ratio of minimum to maximum transmission is 0.8933. The \l/2 correction factor is 0.0015.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.327 _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.827 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4370 _refine_ls_number_restraints 19 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.1139 _refine_ls_R_factor_gt 0.0715 _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^)+(0.1417P)^2^+0.3207P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2062 _refine_ls_wR_factor_ref 0.2455 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2573 _reflns_number_total 4370 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob00432g2.cif _cod_data_source_block sf20180411-2 _cod_database_code 7156741 _shelx_shelxl_version_number 2017/1 _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 0.981 _shelx_estimated_absorpt_t_min 0.954 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C21-C20 1.53 with sigma of 0.005 3. Uiso/Uaniso restraints and constraints O3 \\sim C20 \\sim C21: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 4.a Ternary CH refined with riding coordinates: C1(H1) 4.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C20(H20A,H20B) 4.c Aromatic/amide H refined with riding coordinates: C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18) 4.d Idealised Me refined as rotating group: C21(H21A,H21B,H21C) ; _shelx_res_file ; TITL sf20180411-2_a.res in P2(1)/c sf20180411-2.res created by SHELXL-2017/1 at 18:36:19 on 16-Apr-2018 REM Old TITL sf20180411-2 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.229, Rweak 0.022, Alpha 0.041, Orientation as input REM Formula found by SHELXT: C24 N O3 CELL 0.71073 15.7507 9.3997 12.8142 90 93.56 90 ZERR 4 0.0018 0.0011 0.0015 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 84 72 8 20 DFIX 1.53 0.005 C21 C20 SIMU 0.01 0.02 2 O3 C20 C21 ISOR 0.005 0.01 C21 L.S. 10 PLAN 20 SIZE 0.2 0.2 0.5 TEMP 23 BOND $H list 4 fmap 2 acta OMIT -4 0 4 OMIT 1 0 0 OMIT 2 1 0 OMIT -4 3 2 OMIT -1 1 5 OMIT 0 0 6 REM REM REM WGHT 0.141700 0.320700 FVAR 0.67020 O1 4 0.741298 0.267105 0.369554 11.00000 0.17147 0.07714 = 0.03788 0.00095 0.00936 -0.03921 O2 4 0.575049 0.315031 0.589532 11.00000 0.06098 0.11024 = 0.12090 -0.04829 0.00218 0.00004 O3 4 0.544136 0.515945 0.670234 11.00000 0.05640 0.11688 = 0.12850 -0.03984 0.01929 0.01311 O4 4 0.916774 0.233568 0.699775 11.00000 0.07189 0.07751 = 0.08929 0.01075 -0.00247 0.01599 O5 4 0.955079 0.400808 0.804183 11.00000 0.10725 0.11929 = 0.09299 -0.00583 -0.04877 0.00961 N1 3 0.769962 0.350010 0.531300 11.00000 0.05236 0.04973 = 0.03656 0.00288 0.00818 -0.00336 N2 3 0.907151 0.349531 0.737199 11.00000 0.06217 0.07566 = 0.05563 0.01281 -0.00684 -0.00075 C1 1 0.758544 0.354966 0.645450 11.00000 0.05401 0.04640 = 0.03509 0.00526 0.00798 0.00115 AFIX 13 H1 2 0.756404 0.259874 0.676534 11.00000 -1.20000 AFIX 0 C2 1 0.685396 0.447522 0.674198 11.00000 0.05607 0.05146 = 0.04205 0.00627 0.01357 0.00260 C3 1 0.710687 0.548768 0.742223 11.00000 0.07008 0.05168 = 0.04921 -0.00194 0.01766 0.00183 AFIX 43 H3 2 0.673928 0.615812 0.767967 11.00000 -1.20000 AFIX 0 C4 1 0.802656 0.544170 0.772727 11.00000 0.08015 0.06029 = 0.04801 -0.00515 0.00762 -0.01296 AFIX 23 H4A 2 0.813231 0.506684 0.842857 11.00000 -1.20000 H4B 2 0.828345 0.637644 0.768725 11.00000 -1.20000 AFIX 0 C5 1 0.835697 0.442997 0.690535 11.00000 0.05239 0.05511 = 0.04304 0.00726 -0.00097 -0.00245 C6 1 0.866575 0.516023 0.596191 11.00000 0.04599 0.05120 = 0.05110 0.00725 0.00489 0.00102 C7 1 0.926687 0.622331 0.591421 11.00000 0.05278 0.06185 = 0.06903 0.00667 0.00125 -0.00741 AFIX 43 H7 2 0.954460 0.657715 0.652130 11.00000 -1.20000 AFIX 0 C8 1 0.944759 0.675111 0.494605 11.00000 0.05315 0.06511 = 0.09551 0.01905 0.01667 -0.01168 AFIX 43 H8 2 0.985199 0.746492 0.489671 11.00000 -1.20000 AFIX 0 C9 1 0.903011 0.622156 0.405743 11.00000 0.05748 0.07043 = 0.06975 0.02800 0.02026 0.00304 AFIX 43 H9 2 0.915489 0.659868 0.341368 11.00000 -1.20000 AFIX 0 C10 1 0.843088 0.514840 0.408281 11.00000 0.05644 0.06624 = 0.05015 0.01530 0.01195 0.00702 AFIX 43 H10 2 0.815776 0.479799 0.347172 11.00000 -1.20000 AFIX 0 C11 1 0.825258 0.461392 0.505626 11.00000 0.04314 0.04992 = 0.04638 0.00897 0.00826 0.00334 C12 1 0.740375 0.248089 0.462934 11.00000 0.07658 0.05140 = 0.03955 -0.00007 0.00930 -0.00326 C13 1 0.710417 0.107858 0.502463 11.00000 0.07212 0.04813 = 0.04651 -0.00217 0.01733 -0.00034 C14 1 0.765493 0.020378 0.561857 11.00000 0.07771 0.05765 = 0.07040 0.00604 0.01298 0.00601 AFIX 43 H14 2 0.817713 0.054717 0.588835 11.00000 -1.20000 AFIX 0 C15 1 0.741662 -0.118828 0.580444 11.00000 0.11861 0.05911 = 0.08888 0.01794 0.01793 0.01614 AFIX 43 H15 2 0.778608 -0.178745 0.619057 11.00000 -1.20000 AFIX 0 C16 1 0.663948 -0.168983 0.542308 11.00000 0.12570 0.05620 = 0.09335 0.00500 0.02873 -0.01258 AFIX 43 H16 2 0.648416 -0.262326 0.555817 11.00000 -1.20000 AFIX 0 C17 1 0.610043 -0.083871 0.485449 11.00000 0.10148 0.06784 = 0.07705 -0.00685 0.02410 -0.02256 AFIX 43 H17 2 0.557319 -0.118478 0.460467 11.00000 -1.20000 AFIX 0 C18 1 0.632629 0.053955 0.464183 11.00000 0.07797 0.06138 = 0.05839 -0.00431 0.01326 -0.00565 AFIX 43 H18 2 0.595458 0.111465 0.423821 11.00000 -1.20000 AFIX 0 C19 1 0.596927 0.416336 0.639525 11.00000 0.05495 0.06860 = 0.06224 -0.00150 0.01553 0.00335 C20 1 0.453896 0.499459 0.640058 11.00000 0.05994 0.17751 = 0.13472 -0.03055 0.01290 0.02134 AFIX 23 H20A 2 0.446132 0.430765 0.583786 11.00000 -1.20000 H20B 2 0.430035 0.589632 0.615922 11.00000 -1.20000 AFIX 0 C21 1 0.411344 0.450402 0.731601 11.00000 0.10829 0.28467 = 0.16502 0.03357 0.02512 -0.02756 AFIX 137 H21A 2 0.443741 0.374738 0.764935 11.00000 -1.50000 H21B 2 0.355476 0.416441 0.710179 11.00000 -1.50000 H21C 2 0.406861 0.527801 0.779828 11.00000 -1.50000 AFIX 0 HKLF 4 REM sf20180411-2_a.res in P2(1)/c REM R1 = 0.0715 for 2573 Fo > 4sig(Fo) and 0.1139 for all 4370 data REM 254 parameters refined using 19 restraints END WGHT 0.1415 0.3056 REM Highest difference peak 0.827, deepest hole -0.469, 1-sigma level 0.060 Q1 1 0.4047 0.5743 0.7155 11.00000 0.05 0.83 Q2 1 0.4530 0.4132 0.6844 11.00000 0.05 0.44 Q3 1 0.5350 0.4358 0.7070 11.00000 0.05 0.24 Q4 1 0.8179 0.0530 0.5634 11.00000 0.05 0.19 Q5 1 0.3361 0.4822 0.7010 11.00000 0.05 0.17 Q6 1 0.9171 0.3694 0.8473 11.00000 0.05 0.17 Q7 1 0.5560 0.5722 0.7070 11.00000 0.05 0.16 Q8 1 0.7318 -0.1637 0.5643 11.00000 0.05 0.16 Q9 1 0.7916 -0.0982 0.5940 11.00000 0.05 0.15 Q10 1 0.7444 0.0856 0.5299 11.00000 0.05 0.15 Q11 1 0.7222 0.2852 0.3613 11.00000 0.05 0.15 Q12 1 0.7124 -0.0926 0.6275 11.00000 0.05 0.14 Q13 1 0.7959 0.2220 0.3933 11.00000 0.05 0.13 Q14 1 0.7836 -0.1830 0.4591 11.00000 0.05 0.13 Q15 1 0.8144 0.5729 0.2604 11.00000 0.05 0.13 Q16 1 0.6777 0.6775 0.8393 11.00000 0.05 0.13 Q17 1 0.9404 -0.0247 0.5772 11.00000 0.05 0.13 Q18 1 0.8469 0.4998 0.5567 11.00000 0.05 0.13 Q19 1 0.8354 -0.0923 0.6731 11.00000 0.05 0.13 Q20 1 0.8368 -0.1687 0.7238 11.00000 0.05 0.12 ; _shelx_res_checksum 69714 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O1 O 0.74130(19) 0.2671(3) 0.36955(16) 0.0954(9) Uani 1 1 d . . O2 O 0.57505(14) 0.3150(3) 0.5895(2) 0.0975(9) Uani 1 1 d . . O3 O 0.54414(14) 0.5159(3) 0.6702(2) 0.1000(9) Uani 1 1 d . U O4 O 0.91677(14) 0.2336(3) 0.69978(19) 0.0799(7) Uani 1 1 d . . O5 O 0.95508(17) 0.4008(3) 0.8042(2) 0.1088(10) Uani 1 1 d . . N1 N 0.76996(12) 0.3500(2) 0.53130(15) 0.0460(5) Uani 1 1 d . . N2 N 0.90715(15) 0.3495(3) 0.7372(2) 0.0649(7) Uani 1 1 d . . C1 C 0.75854(15) 0.3550(3) 0.64545(17) 0.0449(6) Uani 1 1 d . . H1 H 0.756404 0.259874 0.676534 0.054 Uiso 1 1 calc R . C2 C 0.68540(15) 0.4475(3) 0.67420(18) 0.0494(6) Uani 1 1 d . . C3 C 0.71069(18) 0.5488(3) 0.7422(2) 0.0564(7) Uani 1 1 d . . H3 H 0.673928 0.615812 0.767967 0.068 Uiso 1 1 calc R . C4 C 0.80266(19) 0.5442(3) 0.7727(2) 0.0627(7) Uani 1 1 d . . H4A H 0.813231 0.506684 0.842857 0.075 Uiso 1 1 calc R . H4B H 0.828345 0.637644 0.768725 0.075 Uiso 1 1 calc R . C5 C 0.83570(15) 0.4430(3) 0.69054(19) 0.0503(6) Uani 1 1 d . . C6 C 0.86657(15) 0.5160(3) 0.5962(2) 0.0493(6) Uani 1 1 d . . C7 C 0.92669(16) 0.6223(3) 0.5914(2) 0.0613(7) Uani 1 1 d . . H7 H 0.954460 0.657715 0.652130 0.074 Uiso 1 1 calc R . C8 C 0.94476(18) 0.6751(3) 0.4946(3) 0.0708(9) Uani 1 1 d . . H8 H 0.985199 0.746492 0.489671 0.085 Uiso 1 1 calc R . C9 C 0.90301(18) 0.6222(3) 0.4057(3) 0.0652(8) Uani 1 1 d . . H9 H 0.915489 0.659868 0.341368 0.078 Uiso 1 1 calc R . C10 C 0.84309(17) 0.5148(3) 0.4083(2) 0.0572(7) Uani 1 1 d . . H10 H 0.815776 0.479799 0.347172 0.069 Uiso 1 1 calc R . C11 C 0.82526(14) 0.4614(3) 0.50563(19) 0.0463(6) Uani 1 1 d . . C12 C 0.74038(18) 0.2481(3) 0.4629(2) 0.0556(7) Uani 1 1 d . . C13 C 0.71042(18) 0.1079(3) 0.5025(2) 0.0550(7) Uani 1 1 d . . C14 C 0.7655(2) 0.0204(3) 0.5619(2) 0.0682(8) Uani 1 1 d . . H14 H 0.817713 0.054717 0.588835 0.082 Uiso 1 1 calc R . C15 C 0.7417(3) -0.1188(4) 0.5804(3) 0.0884(11) Uani 1 1 d . . H15 H 0.778608 -0.178745 0.619057 0.106 Uiso 1 1 calc R . C16 C 0.6639(3) -0.1690(4) 0.5423(3) 0.0908(11) Uani 1 1 d . . H16 H 0.648416 -0.262326 0.555817 0.109 Uiso 1 1 calc R . C17 C 0.6100(2) -0.0839(4) 0.4854(3) 0.0813(10) Uani 1 1 d . . H17 H 0.557319 -0.118478 0.460467 0.098 Uiso 1 1 calc R . C18 C 0.6326(2) 0.0540(3) 0.4642(2) 0.0655(8) Uani 1 1 d . . H18 H 0.595458 0.111465 0.423821 0.079 Uiso 1 1 calc R . C19 C 0.59693(17) 0.4163(3) 0.6395(2) 0.0614(7) Uani 1 1 d . . C20 C 0.4539(2) 0.4995(6) 0.6401(4) 0.1238(16) Uani 1 1 d D U H20A H 0.446132 0.430765 0.583786 0.149 Uiso 1 1 calc R . H20B H 0.430035 0.589632 0.615922 0.149 Uiso 1 1 calc R . C21 C 0.4113(3) 0.4504(9) 0.7316(5) 0.185(3) Uani 1 1 d D U H21A H 0.443741 0.374738 0.764935 0.278 Uiso 1 1 calc GR . H21B H 0.355476 0.416441 0.710179 0.278 Uiso 1 1 calc GR . H21C H 0.406861 0.527801 0.779828 0.278 Uiso 1 1 calc GR . 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 O1 0.171(3) 0.0771(15) 0.0379(11) 0.0010(10) 0.0094(13) -0.0392(15) O2 0.0610(13) 0.110(2) 0.121(2) -0.0483(17) 0.0022(13) 0.0000(13) O3 0.0564(13) 0.1169(19) 0.129(2) -0.0398(17) 0.0193(13) 0.0131(12) O4 0.0719(14) 0.0775(15) 0.0893(17) 0.0107(13) -0.0025(12) 0.0160(12) O5 0.1073(19) 0.119(2) 0.0930(19) -0.0058(17) -0.0488(16) 0.0096(17) N1 0.0524(11) 0.0497(11) 0.0366(10) 0.0029(8) 0.0082(8) -0.0034(9) N2 0.0622(14) 0.0757(17) 0.0556(14) 0.0128(12) -0.0068(11) -0.0008(13) C1 0.0540(13) 0.0464(13) 0.0351(11) 0.0053(9) 0.0080(10) 0.0012(10) C2 0.0561(14) 0.0515(14) 0.0421(13) 0.0063(10) 0.0136(11) 0.0026(11) C3 0.0701(17) 0.0517(15) 0.0492(14) -0.0019(11) 0.0177(12) 0.0018(12) C4 0.0802(19) 0.0603(16) 0.0480(15) -0.0051(12) 0.0076(13) -0.0130(14) C5 0.0524(14) 0.0551(14) 0.0430(13) 0.0073(11) -0.0010(10) -0.0025(11) C6 0.0460(13) 0.0512(14) 0.0511(14) 0.0072(11) 0.0049(10) 0.0010(11) C7 0.0528(15) 0.0619(17) 0.0690(18) 0.0067(14) 0.0013(13) -0.0074(13) C8 0.0532(16) 0.0651(18) 0.096(2) 0.0190(17) 0.0167(16) -0.0117(14) C9 0.0575(16) 0.0704(18) 0.0697(18) 0.0280(15) 0.0203(14) 0.0030(14) C10 0.0564(15) 0.0662(16) 0.0501(15) 0.0153(12) 0.0120(11) 0.0070(13) C11 0.0431(12) 0.0499(13) 0.0464(13) 0.0090(10) 0.0083(10) 0.0033(10) C12 0.0766(18) 0.0514(14) 0.0396(14) -0.0001(11) 0.0093(12) -0.0033(13) C13 0.0721(17) 0.0481(14) 0.0465(14) -0.0022(11) 0.0173(12) -0.0003(12) C14 0.078(2) 0.0577(17) 0.0704(19) 0.0060(14) 0.0130(15) 0.0060(14) C15 0.119(3) 0.0591(19) 0.089(2) 0.0179(17) 0.018(2) 0.016(2) C16 0.126(3) 0.0562(19) 0.093(3) 0.0050(18) 0.029(2) -0.013(2) C17 0.101(3) 0.068(2) 0.077(2) -0.0069(17) 0.0241(19) -0.0226(19) C18 0.0780(19) 0.0614(17) 0.0584(17) -0.0043(13) 0.0133(14) -0.0056(15) C19 0.0549(15) 0.0686(18) 0.0622(17) -0.0015(14) 0.0155(13) 0.0034(14) C20 0.060(2) 0.178(4) 0.135(4) -0.031(3) 0.013(2) 0.021(2) C21 0.108(4) 0.285(7) 0.165(5) 0.034(5) 0.025(4) -0.028(4) 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 C19 O3 C20 117.7(3) C11 N1 C1 108.66(18) C12 N1 C1 126.8(2) C12 N1 C11 124.3(2) O4 N2 O5 123.8(3) O4 N2 C5 118.3(2) O5 N2 C5 117.6(3) N1 C1 H1 112.4 N1 C1 C2 113.57(19) N1 C1 C5 104.09(18) C2 C1 H1 112.4 C2 C1 C5 101.2(2) C5 C1 H1 112.4 C3 C2 C1 111.7(2) C3 C2 C19 125.5(2) C19 C2 C1 122.5(2) C2 C3 H3 123.2 C2 C3 C4 113.6(2) C4 C3 H3 123.2 C3 C4 H4A 111.4 C3 C4 H4B 111.4 C3 C4 C5 101.9(2) H4A C4 H4B 109.3 C5 C4 H4A 111.4 C5 C4 H4B 111.4 N2 C5 C1 112.4(2) N2 C5 C4 111.3(2) C4 C5 C1 107.2(2) C6 C5 N2 108.2(2) C6 C5 C1 103.29(19) C6 C5 C4 114.3(2) C7 C6 C5 128.7(2) C7 C6 C11 121.1(2) C11 C6 C5 110.2(2) C6 C7 H7 120.7 C6 C7 C8 118.7(3) C8 C7 H7 120.7 C7 C8 H8 120.0 C9 C8 C7 120.0(3) C9 C8 H8 120.0 C8 C9 H9 118.7 C8 C9 C10 122.5(3) C10 C9 H9 118.7 C9 C10 H10 121.3 C9 C10 C11 117.5(3) C11 C10 H10 121.3 C6 C11 N1 110.0(2) C10 C11 N1 129.7(2) C10 C11 C6 120.3(2) O1 C12 N1 120.5(2) O1 C12 C13 119.2(2) N1 C12 C13 120.3(2) C14 C13 C12 120.5(3) C18 C13 C12 119.4(3) C18 C13 C14 119.1(3) C13 C14 H14 120.4 C15 C14 C13 119.1(3) C15 C14 H14 120.4 C14 C15 H15 119.7 C16 C15 C14 120.5(3) C16 C15 H15 119.7 C15 C16 H16 119.8 C17 C16 C15 120.4(3) C17 C16 H16 119.8 C16 C17 H17 119.9 C16 C17 C18 120.3(4) C18 C17 H17 119.9 C13 C18 H18 119.7 C17 C18 C13 120.5(3) C17 C18 H18 119.7 O2 C19 O3 124.0(3) O2 C19 C2 124.3(3) O3 C19 C2 111.7(3) O3 C20 H20A 110.1 O3 C20 H20B 110.1 O3 C20 C21 108.0(4) H20A C20 H20B 108.4 C21 C20 H20A 110.1 C21 C20 H20B 110.1 C20 C21 H21A 109.5 C20 C21 H21B 109.5 C20 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C12 1.211(3) O2 C19 1.187(4) O3 C19 1.328(4) O3 C20 1.458(4) O4 N2 1.204(3) O5 N2 1.208(3) N1 C1 1.486(3) N1 C11 1.414(3) N1 C12 1.361(3) N2 C5 1.521(3) C1 H1 0.9800 C1 C2 1.508(3) C1 C5 1.552(3) C2 C3 1.335(4) C2 C19 1.466(4) C3 H3 0.9300 C3 C4 1.477(4) C4 H4A 0.9700 C4 H4B 0.9700 C4 C5 1.534(4) C5 C6 1.497(3) C6 C7 1.381(4) C6 C11 1.393(4) C7 H7 0.9300 C7 C8 1.382(4) C8 H8 0.9300 C8 C9 1.373(5) C9 H9 0.9300 C9 C10 1.383(4) C10 H10 0.9300 C10 C11 1.390(3) C12 C13 1.499(4) C13 C14 1.388(4) C13 C18 1.387(4) C14 H14 0.9300 C14 C15 1.386(5) C15 H15 0.9300 C15 C16 1.373(5) C16 H16 0.9300 C16 C17 1.347(5) C17 H17 0.9300 C17 C18 1.375(4) C18 H18 0.9300 C20 H20A 0.9700 C20 H20B 0.9700 C20 C21 1.461(4) C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600