#------------------------------------------------------------------------------ #$Date: 2015-07-10 23:58:32 +0300 (Fri, 10 Jul 2015) $ #$Revision: 143438 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/94/1519444.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_1519444 loop_ _publ_author_name 'Hean, D.' 'Gelbrich, T.' 'Griesser, U. J.' 'Michael, J. P.' 'Lemmerer, A.' _publ_section_title ; Structural insights into the hexamorphic system of an isoniazid derivative ; _journal_issue 28 _journal_name_full CrystEngComm _journal_page_first 5143 _journal_paper_doi 10.1039/C5CE00275C _journal_volume 17 _journal_year 2015 _chemical_formula_moiety 'C14 H13 N3 O' _chemical_formula_sum 'C14 H13 N3 O' _chemical_formula_weight 239.27 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _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 direct _atom_sites_solution_secondary difmap _audit_creation_date 2013-10-31T14:02:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2013-11-06 deposited with the CCDC. 2015-03-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.183(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.488(2) _cell_length_b 9.6611(15) _cell_length_c 9.3604(13) _cell_measurement_reflns_used 6777 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.28 _cell_measurement_theta_min 3.02 _cell_volume 1219.7(3) _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_collection 'APEX3 (Bruker, 2005)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.069 _diffrn_reflns_av_unetI/netI 0.0498 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 20120 _diffrn_reflns_theta_full 28 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_min 3.03 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_meas 0 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.487 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.11 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2900 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0729 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1353P)^2^+0.8927P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1936 _refine_ls_wR_factor_ref 0.2468 _reflns_number_gt 1992 _reflns_number_total 2900 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 11a_DH40_p in P2(1)/c CELL 0.71073 10.2114 30.3315 8.2353 90.000 110.193 90.000 ZERR 8.00 0.0002 0.0007 0.0002 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 112 104 24 8 MERG 2 OMIT -2.00 56.00 OMIT 1 1 0 OMIT 1 2 0 OMIT 0 4 0 OMIT 0 1 1 EQIV $2 x, -y+1/2, z-1/2 EQIV $3 -x+2, -y, -z+2 HTAB N1A O1A_$2 HTAB N1B N2B_$3 FMAP 2 PLAN 2 SIZE 0.10 0.28 0.55 ACTA BOND BOND $H CONF L.S. 4 TEMP -100.00 WGHT 0.083100 0.824400 FVAR 0.12626 MOLE 1 C1A 1 0.236178 0.285231 -0.066121 11.00000 0.02118 0.02975 = 0.01961 0.00440 0.00590 0.00029 C2A 1 0.158951 0.253967 -0.183090 11.00000 0.02605 0.03179 = 0.02504 0.00238 0.00441 0.00076 AFIX 43 H2A 2 0.182356 0.223580 -0.166798 11.00000 -1.20000 AFIX 0 C3A 1 0.046752 0.267988 -0.324459 11.00000 0.02531 0.04799 = 0.02246 0.00212 0.00378 -0.00139 AFIX 43 H3A 2 -0.005764 0.246352 -0.403697 11.00000 -1.20000 AFIX 0 C4A 1 0.082275 0.339459 -0.239489 11.00000 0.03426 0.03684 = 0.04024 0.01479 0.00968 0.00889 AFIX 43 H4A 2 0.055815 0.369572 -0.258397 11.00000 -1.20000 AFIX 0 C5A 1 0.194940 0.328932 -0.093400 11.00000 0.02933 0.02966 = 0.03042 0.00438 0.00873 0.00100 AFIX 43 H5A 2 0.242841 0.351157 -0.013740 11.00000 -1.20000 AFIX 0 C6A 1 0.355941 0.273804 0.094616 11.00000 0.02342 0.02556 = 0.01966 0.00226 0.00342 -0.00267 C7A 1 0.623403 0.195661 0.226331 11.00000 0.02241 0.02779 = 0.01853 0.00166 0.00321 -0.00256 C8A 1 0.721264 0.180431 0.397267 11.00000 0.02229 0.02637 = 0.01983 0.00209 0.00399 -0.00073 C9A 1 0.720079 0.199866 0.550602 11.00000 0.02978 0.03244 = 0.02327 -0.00047 0.00357 0.00713 AFIX 43 H9A 2 0.654800 0.222587 0.545754 11.00000 -1.20000 AFIX 0 C10A 1 0.812762 0.186471 0.709620 11.00000 0.03455 0.03614 = 0.02015 -0.00030 0.00396 0.00139 AFIX 43 H10A 2 0.810908 0.200125 0.812622 11.00000 -1.20000 AFIX 0 C11A 1 0.907859 0.153321 0.718853 11.00000 0.03228 0.03477 = 0.02298 0.00801 0.00132 0.00237 AFIX 43 H11A 2 0.972463 0.144513 0.827759 11.00000 -1.20000 AFIX 0 C12A 1 0.908535 0.133096 0.569291 11.00000 0.03766 0.03946 = 0.03006 0.00624 0.00647 0.01574 AFIX 43 H12A 2 0.972640 0.109920 0.575390 11.00000 -1.20000 AFIX 0 C13A 1 0.815579 0.146506 0.409204 11.00000 0.03479 0.03776 = 0.02334 0.00113 0.00694 0.00977 AFIX 43 H13A 2 0.816685 0.132278 0.306916 11.00000 -1.20000 AFIX 0 C14A 1 0.640415 0.177536 0.065269 11.00000 0.02603 0.04635 = 0.02024 0.00033 0.00502 0.00494 AFIX 137 H14A 2 0.606326 0.147087 0.047559 11.00000 -1.50000 H14B 2 0.739287 0.178142 0.077309 11.00000 -1.50000 H14C 2 0.586744 0.195541 -0.034269 11.00000 -1.50000 AFIX 0 N1A 3 0.432449 0.238348 0.082751 11.00000 0.02411 0.02899 = 0.01620 0.00216 0.00036 0.00195 H1A 2 0.423227 0.228171 -0.024718 11.00000 0.03966 N2A 3 0.008512 0.310007 -0.355385 11.00000 0.02755 0.05305 = 0.02860 0.01286 0.00458 0.00667 N3A 3 0.531657 0.223770 0.235202 11.00000 0.02368 0.02723 = 0.01823 0.00291 0.00033 0.00110 O1A 4 0.377631 0.295707 0.226602 11.00000 0.03487 0.03220 = 0.02187 -0.00283 0.00180 0.00253 MOLE 2 C1B 1 0.940496 -0.037279 0.747180 11.00000 0.02570 0.02175 = 0.02318 -0.00113 0.00263 0.00304 C2B 1 1.081672 -0.042280 0.773000 11.00000 0.02915 0.03374 = 0.02878 0.00113 0.00986 0.00617 AFIX 43 H2B 2 1.115698 -0.038929 0.679921 11.00000 -1.20000 AFIX 0 C3B 1 1.171459 -0.052293 0.938330 11.00000 0.02191 0.03425 = 0.03562 0.00005 0.00435 0.00537 AFIX 43 H3B 2 1.268062 -0.055200 0.956133 11.00000 -1.20000 AFIX 0 C4B 1 0.992989 -0.055193 1.044880 11.00000 0.02929 0.02332 = 0.02542 0.00351 0.00502 -0.00057 AFIX 43 H4B 2 0.960972 -0.060623 1.138502 11.00000 -1.20000 AFIX 0 C5B 1 0.895270 -0.044692 0.885261 11.00000 0.02176 0.02313 = 0.02681 0.00124 0.00369 -0.00053 AFIX 43 H5B 2 0.799058 -0.042614 0.870766 11.00000 -1.20000 AFIX 0 C6B 1 0.841289 -0.024530 0.571482 11.00000 0.02937 0.03178 = 0.02276 -0.00028 0.00383 0.00508 C7B 1 0.577411 0.055515 0.427966 11.00000 0.01968 0.03120 = 0.02033 0.00007 0.00338 0.00042 C8B 1 0.484974 0.072534 0.257220 11.00000 0.01844 0.03180 = 0.02150 0.00233 0.00518 0.00027 C9B 1 0.463449 0.048007 0.106668 11.00000 0.02771 0.03809 = 0.02200 0.00026 0.00470 0.00816 AFIX 43 H9B 2 0.507454 0.020111 0.114167 11.00000 -1.20000 AFIX 0 C10B 1 0.379035 0.063621 -0.053554 11.00000 0.03134 0.04966 = 0.02029 0.00176 0.00567 0.00451 AFIX 43 H10B 2 0.364894 0.046348 -0.154419 11.00000 -1.20000 AFIX 0 C11B 1 0.315408 0.104400 -0.066342 11.00000 0.02505 0.04494 = 0.02571 0.01238 0.00440 0.00101 AFIX 43 H11B 2 0.259092 0.115503 -0.176118 11.00000 -1.20000 AFIX 0 C12B 1 0.334328 0.128845 0.081550 11.00000 0.02647 0.02944 = 0.03836 0.00971 0.00809 0.00132 AFIX 43 H12B 2 0.289506 0.156626 0.073182 11.00000 -1.20000 AFIX 0 C13B 1 0.418344 0.113198 0.242610 11.00000 0.02341 0.02729 = 0.02881 0.00041 0.00619 -0.00081 AFIX 43 H13B 2 0.430378 0.130340 0.343285 11.00000 -1.20000 AFIX 0 C14B 1 0.565848 0.074116 0.591142 11.00000 0.03279 0.05172 = 0.02245 -0.00204 0.00538 0.01283 AFIX 137 H14D 2 0.584010 0.050803 0.678548 11.00000 -1.50000 H14E 2 0.471674 0.085879 0.567359 11.00000 -1.50000 H14F 2 0.634303 0.097827 0.634182 11.00000 -1.50000 AFIX 0 N1B 3 0.753810 0.008972 0.575946 11.00000 0.02602 0.03331 = 0.01795 0.00074 0.00118 0.00663 H1B 2 0.771519 0.023560 0.671535 11.00000 0.03956 N2B 3 1.129844 -0.058096 1.074265 11.00000 0.02670 0.02857 = 0.02859 0.00330 0.00054 0.00306 N3B 3 0.662310 0.024955 0.420095 11.00000 0.02360 0.03283 = 0.01870 0.00188 0.00194 0.00434 O1B 4 0.842357 -0.043054 0.440837 11.00000 0.05483 0.05152 = 0.02409 -0.00639 0.00098 0.02380 HKLF 4 REM 11a_DH40_p in P2(1)/c REM R1 = 0.0400 for 4579 Fo > 4sig(Fo) and 0.0532 for all 5778 data REM 335 parameters refined using 0 restraints END WGHT 0.0537 0.5727 REM Highest difference peak 0.313, deepest hole -0.174, 1-sigma level 0.039 Q1 1 0.2963 0.2803 0.0059 11.00000 0.05 0.31 Q2 1 0.5204 0.0626 0.3472 11.00000 0.05 0.31 ; _cod_data_source_file c5ce00275c2.cif _cod_data_source_block 13a_dh_form_vlt_p _cod_depositor_comments 'Adding full bibliography for 1519444--1519449.cif.' _cod_cif_authors_sg_H-M P2(1)/c _cod_database_code 1519444 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.26804(18) 0.3146(3) 0.0474(3) 0.0271(6) Uani 1 1 d . C2 C 0.21844(18) 0.2268(3) 0.1386(3) 0.0329(6) Uani 1 1 d . H2 H 0.2491 0.1443 0.1721 0.04 Uiso 1 1 calc R C3 C 0.12278(19) 0.2611(3) 0.1807(3) 0.0404(7) Uani 1 1 d . H3 H 0.0891 0.1991 0.2426 0.049 Uiso 1 1 calc R C4 C 0.1248(2) 0.4614(3) 0.0522(4) 0.0424(7) Uani 1 1 d . H4 H 0.093 0.5443 0.0223 0.051 Uiso 1 1 calc R C5 C 0.2196(2) 0.4352(3) 0.0035(3) 0.0353(6) Uani 1 1 d . H5 H 0.2515 0.4985 -0.059 0.042 Uiso 1 1 calc R C6 C 0.36850(17) 0.2865(3) -0.0145(3) 0.0262(5) Uani 1 1 d . C7 C 0.56342(19) 0.0340(3) 0.2131(3) 0.0305(6) Uani 1 1 d . H7A H 0.5707 0.0917 0.2986 0.046 Uiso 1 1 calc R H7B H 0.6085 -0.0453 0.2195 0.046 Uiso 1 1 calc R H7C H 0.4949 0.0009 0.206 0.046 Uiso 1 1 calc R C8 C 0.58814(18) 0.1180(2) 0.0831(3) 0.0259(5) Uani 1 1 d . C9 C 0.69004(18) 0.1113(2) 0.0213(3) 0.0290(6) Uani 1 1 d . C10 C 0.7086(2) 0.1553(3) -0.1167(3) 0.0346(6) Uani 1 1 d . H10 H 0.6551 0.1854 -0.1752 0.042 Uiso 1 1 calc R C11 C 0.8041(2) 0.1560(3) -0.1708(4) 0.0408(7) Uani 1 1 d . H11 H 0.8156 0.1835 -0.2668 0.049 Uiso 1 1 calc R C12 C 0.8833(2) 0.1163(3) -0.0840(4) 0.0463(8) Uani 1 1 d . H12 H 0.9493 0.1208 -0.1192 0.056 Uiso 1 1 calc R C13 C 0.8659(2) 0.0707(3) 0.0520(4) 0.0451(8) Uani 1 1 d . H13 H 0.9198 0.0415 0.1102 0.054 Uiso 1 1 calc R C14 C 0.7701(2) 0.0667(3) 0.1059(3) 0.0357(6) Uani 1 1 d . H14 H 0.7586 0.0337 0.2 0.043 Uiso 1 1 calc R N1 N 0.43312(15) 0.2132(2) 0.0673(2) 0.0268(5) Uani 1 1 d . N2 N 0.07526(18) 0.3760(3) 0.1394(3) 0.0438(7) Uani 1 1 d . N3 N 0.52849(15) 0.1985(2) 0.0149(2) 0.0274(5) Uani 1 1 d . O1 O 0.38732(14) 0.3280(2) -0.1346(2) 0.0371(5) Uani 1 1 d . H1 H 0.416(2) 0.195(3) 0.163(4) 0.031(8) Uiso 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 0.0276(12) 0.0311(13) 0.0226(13) -0.0038(10) -0.0025(9) 0.0026(9) C2 0.0296(13) 0.0333(13) 0.0359(15) 0.0010(11) 0.0011(10) 0.0012(10) C3 0.0301(14) 0.0450(17) 0.0463(18) -0.0019(14) 0.0059(12) -0.0001(12) C4 0.0353(15) 0.0464(17) 0.0455(18) -0.0026(14) -0.0057(12) 0.0122(12) C5 0.0357(14) 0.0393(15) 0.0310(15) 0.0014(11) -0.0006(11) 0.0083(11) C6 0.0291(12) 0.0291(12) 0.0204(12) -0.0025(9) 0.0015(9) 0.0007(9) C7 0.0333(13) 0.0294(13) 0.0288(14) 0.0003(10) 0.0025(10) 0.0038(10) C8 0.0313(12) 0.0225(11) 0.0240(13) -0.0064(9) 0.0003(9) 0.0002(9) C9 0.0298(12) 0.0218(12) 0.0354(15) -0.0058(10) 0.0036(10) 0.0021(9) C10 0.0346(14) 0.0267(13) 0.0426(16) 0.0044(11) 0.0067(11) 0.0058(10) C11 0.0479(16) 0.0279(13) 0.0467(18) 0.0074(12) 0.0205(13) 0.0026(12) C12 0.0288(14) 0.0339(15) 0.076(2) 0.0009(15) 0.0151(14) 0.0027(11) C13 0.0323(14) 0.0454(17) 0.058(2) -0.0114(15) -0.0001(13) 0.0081(12) C14 0.0347(14) 0.0373(15) 0.0349(16) -0.0021(12) 0.0005(11) 0.0047(11) N1 0.0253(10) 0.0319(11) 0.0233(11) -0.0001(8) 0.0029(8) 0.0038(8) N2 0.0297(12) 0.0525(16) 0.0493(16) -0.0016(13) 0.0023(10) 0.0066(11) N3 0.0287(10) 0.0295(11) 0.0241(11) -0.0037(8) 0.0032(8) 0.0046(8) O1 0.0367(10) 0.0499(12) 0.0248(10) 0.0061(9) 0.0039(7) 0.0063(8) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 -1 0.184 0 1 1 0.156 -1 -2 2 0.123 0 1 0 0.111 0 -1 0 0.181 -1 0 0 0.019 1 0 0 0.022 0 0 -1 0.189 0 0 1 0.157 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C5 117.9(2) C2 C1 C6 124.7(2) C5 C1 C6 117.3(2) C1 C2 C3 118.8(3) C1 C2 H2 120.6 C3 C2 H2 120.6 N2 C3 C2 124.0(3) N2 C3 H3 118 C2 C3 H3 118 N2 C4 C5 123.5(3) N2 C4 H4 118.3 C5 C4 H4 118.3 C4 C5 C1 119.2(3) C4 C5 H5 120.4 C1 C5 H5 120.4 O1 C6 N1 123.8(2) O1 C6 C1 119.1(2) N1 C6 C1 117.1(2) C8 C7 H7A 109.5 C8 C7 H7B 109.5 H7A C7 H7B 109.5 C8 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 N3 C8 C9 114.1(2) N3 C8 C7 126.1(2) C9 C8 C7 119.8(2) C10 C9 C14 118.7(2) C10 C9 C8 121.2(2) C14 C9 C8 120.1(2) C9 C10 C11 120.9(3) C9 C10 H10 119.5 C11 C10 H10 119.5 C10 C11 C12 119.8(3) C10 C11 H11 120.1 C12 C11 H11 120.1 C13 C12 C11 119.8(3) C13 C12 H12 120.1 C11 C12 H12 120.1 C12 C13 C14 120.6(3) C12 C13 H13 119.7 C14 C13 H13 119.7 C13 C14 C9 120.1(3) C13 C14 H14 120 C9 C14 H14 120 C6 N1 N3 116.6(2) C6 N1 H1 118.6(18) N3 N1 H1 123.0(18) C3 N2 C4 116.6(3) C8 N3 N1 117.8(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.378(4) C1 C5 1.397(4) C1 C6 1.500(3) C2 C3 1.390(4) C2 H2 0.95 C3 N2 1.338(4) C3 H3 0.95 C4 N2 1.340(4) C4 C5 1.383(4) C4 H4 0.95 C5 H5 0.95 C6 O1 1.221(3) C6 N1 1.358(3) C7 C8 1.501(4) C7 H7A 0.98 C7 H7B 0.98 C7 H7C 0.98 C8 N3 1.287(3) C8 C9 1.494(3) C9 C10 1.383(4) C9 C14 1.404(4) C10 C11 1.387(4) C10 H10 0.95 C11 C12 1.394(5) C11 H11 0.95 C12 C13 1.369(5) C12 H12 0.95 C13 C14 1.389(4) C13 H13 0.95 C14 H14 0.95 N1 N3 1.386(3) N1 H1 0.94(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.94(3) 1.95(3) 2.887(3) 175(3) 4_566 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 C5 C1 C2 C3 0.9(4) C6 C1 C2 C3 -175.7(2) C1 C2 C3 N2 -0.8(4) N2 C4 C5 C1 -0.7(5) C2 C1 C5 C4 -0.2(4) C6 C1 C5 C4 176.7(2) C2 C1 C6 O1 146.4(3) C5 C1 C6 O1 -30.3(3) C2 C1 C6 N1 -32.6(4) C5 C1 C6 N1 150.8(2) N3 C8 C9 C10 -17.4(3) C7 C8 C9 C10 162.2(2) N3 C8 C9 C14 159.2(2) C7 C8 C9 C14 -21.2(3) C14 C9 C10 C11 -0.2(4) C8 C9 C10 C11 176.4(2) C9 C10 C11 C12 -2.1(4) C10 C11 C12 C13 3.0(5) C11 C12 C13 C14 -1.5(5) C12 C13 C14 C9 -0.8(4) C10 C9 C14 C13 1.7(4) C8 C9 C14 C13 -175.0(2) O1 C6 N1 N3 6.7(4) C1 C6 N1 N3 -174.3(2) C2 C3 N2 C4 -0.1(5) C5 C4 N2 C3 0.8(5) C9 C8 N3 N1 -178.4(2) C7 C8 N3 N1 2.0(4) C6 N1 N3 C8 -173.1(2)