#------------------------------------------------------------------------------ #$Date: 2023-04-20 14:53:48 +0300 (Thu, 20 Apr 2023) $ #$Revision: 282777 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/64/1546491.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_1546491 loop_ _publ_author_name 'Wicker, Jerome G. P.' 'Crowley, Lorraine M.' 'Robshaw, Oliver' 'Little, Edmund J.' 'Stokes, Stephen P.' 'Cooper, Richard I.' 'Lawrence, Simon E.' _publ_section_title ; Will they co-crystallize? ; _journal_issue 36 _journal_name_full CrystEngComm _journal_page_first 5336 _journal_page_last 5340 _journal_paper_doi 10.1039/C7CE00587C _journal_volume 19 _journal_year 2017 _chemical_formula_moiety '2(C7 H5 N O4), C H4 N2 O' _chemical_formula_sum 'C15 H14 N4 O9' _chemical_formula_weight 394.30 _chemical_name_common 'Urea + 2Nitrobenzoic Acid from MecN' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2017-03-17 deposited with the CCDC. 2017-07-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.953(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.8242(18) _cell_length_b 10.0350(15) _cell_length_c 15.060(2) _cell_measurement_reflns_used 7970 _cell_measurement_temperature 296.(2) _cell_measurement_theta_max 24.9711 _cell_measurement_theta_min 2.4655 _cell_volume 1726.4(4) _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_collection 'Bruker Instrument Service v2013.12.0.0' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX DUO' _diffrn_measurement_method '\w and \q scans' _diffrn_radiation_monochromator Graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_unetI/netI 0.0169 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 22669 _diffrn_reflns_theta_full 25.14 _diffrn_reflns_theta_max 25.14 _diffrn_reflns_theta_min 1.96 _diffrn_source 'Sealed tube' _diffrn_source_type 'Siemens KFF Mo 2K-90' _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5 (Bruker AXS Inc.)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.504 _exptl_crystal_size_mid 0.415 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.210 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 3077 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0536P)^2^+0.3329P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.1012 _reflns_number_gt 2530 _reflns_number_total 3077 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce00587c3.cif _cod_data_source_block 6A _cod_database_code 1546491 _shelx_res_file ; mo_SEL_LC_6A_AcN_P21c_0m_a.res created by SHELXL-2014/7 TITL mo_SEL_LC_6A_AcN_P21c_0m_a.res in P2(1)/n CELL 0.71073 11.8242 10.0350 15.0599 90.000 104.953 90.000 ZERR 4.000 0.0018 0.0015 0.0022 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 60 56 16 36 REM Old TITL mo_SEL_LC_6A_AcN_P21c_0m in P2(1)/c REM SHELXT solution in P2(1)/n REM R1 0.218, Rweak 0.006, Alpha 0.020, Orientation as input REM Formula found by SHELXT: C21 N2 O5 L.S. 10 ACTA BOND $H HTAB O8 O14 HTAB N15 O9 HTAB N15 O29_$1 HTAB N16 O32_$2 HTAB N16 O29_$3 HTAB O28 O14_$4 EQIV $1 [ -x+3/2, y-1/2, -z+1/2 ] EQIV $2 [ -x+3/2, y-1/2, -z+1/2 ] EQIV $3 [ x, y-1, z ] EQIV $4 [ x, y+1, z ] DFIX 0.82 0.01 O8 H8 O28 H28 DFIX 0.89 0.01 N15 H15A N15 H15B N16 H16A N16 H16B CONF FMAP 2 PLAN 5 SIZE 0.150 0.415 0.504 TEMP 23.000 WGHT 0.053600 0.332900 FVAR 0.40240 C1 1 0.694312 0.618528 0.681408 11.00000 0.05581 0.04316 = 0.04229 0.00699 0.00563 0.00047 AFIX 43 H1 2 0.736479 0.540082 0.697568 11.00000 -1.20000 AFIX 0 C2 1 0.681242 0.703849 0.749465 11.00000 0.06569 0.05826 = 0.03617 0.00031 0.00681 -0.01475 AFIX 43 H2 2 0.716176 0.683748 0.810689 11.00000 -1.20000 AFIX 0 C3 1 0.617038 0.818297 0.727563 11.00000 0.07133 0.04807 = 0.04576 -0.01067 0.02230 -0.01225 AFIX 43 H3 2 0.606132 0.874115 0.773950 11.00000 -1.20000 AFIX 0 C4 1 0.568820 0.850619 0.637238 11.00000 0.06376 0.03907 = 0.05235 -0.00161 0.01978 0.00046 AFIX 43 H4 2 0.525937 0.928745 0.621828 11.00000 -1.20000 AFIX 0 C5 1 0.584819 0.765741 0.569716 11.00000 0.04614 0.03693 = 0.03756 0.00253 0.01062 -0.00171 C6 1 0.646047 0.646659 0.589062 11.00000 0.04317 0.03473 = 0.03975 0.00164 0.00874 -0.00296 C7 1 0.652196 0.549308 0.516096 11.00000 0.04630 0.03290 = 0.04229 0.00349 0.00905 -0.00029 O8 4 0.730944 0.456391 0.545100 11.00000 0.08147 0.04829 = 0.05089 -0.00577 0.00122 0.02450 H8 2 0.725854 0.399508 0.503420 11.00000 0.08757 O9 4 0.589407 0.554096 0.438953 11.00000 0.06194 0.04421 = 0.04155 -0.00312 0.00474 0.00493 N10 3 0.538723 0.811289 0.474825 11.00000 0.06139 0.04151 = 0.04413 0.00274 0.01081 0.00852 O11 4 0.608074 0.845805 0.432876 11.00000 0.08853 0.07044 = 0.04911 0.01096 0.01997 -0.01322 O12 4 0.434279 0.817681 0.444123 11.00000 0.06148 0.14771 = 0.06686 0.02397 0.00544 0.03274 C13 1 0.699829 0.264415 0.339864 11.00000 0.04915 0.04514 = 0.04282 0.00180 0.00941 0.00212 O14 4 0.731217 0.264532 0.426116 11.00000 0.07508 0.04550 = 0.04049 0.00062 0.01158 0.01589 N15 3 0.651530 0.373019 0.294575 11.00000 0.07991 0.05334 = 0.04429 0.00718 0.00731 0.01342 H15A 2 0.629808 0.437876 0.326614 11.00000 0.07436 H15B 2 0.626342 0.371027 0.234985 11.00000 0.06992 N16 3 0.714426 0.156819 0.293265 11.00000 0.08484 0.05719 = 0.03957 -0.00435 0.00785 0.01716 H16A 2 0.698304 0.157005 0.232836 11.00000 0.07260 H16B 2 0.757854 0.090506 0.321925 11.00000 0.06983 C21 1 0.921043 0.890269 0.663284 11.00000 0.06355 0.04190 = 0.03964 -0.00562 0.01639 0.00046 AFIX 43 H21 2 0.894393 0.970746 0.680889 11.00000 -1.20000 AFIX 0 C22 1 0.975700 0.801209 0.729811 11.00000 0.07411 0.05600 = 0.03465 0.00115 0.01132 -0.00294 AFIX 43 H22 2 0.984886 0.821422 0.791535 11.00000 -1.20000 AFIX 0 C23 1 1.016675 0.682800 0.705488 11.00000 0.07842 0.05317 = 0.04572 0.01044 0.00789 0.00705 AFIX 43 H23 2 1.054107 0.622957 0.750717 11.00000 -1.20000 AFIX 0 C24 1 1.002647 0.652228 0.614563 11.00000 0.07555 0.04020 = 0.05413 0.00024 0.01397 0.01221 AFIX 43 H24 2 1.030737 0.572143 0.597632 11.00000 -1.20000 AFIX 0 C25 1 0.946371 0.741827 0.548716 11.00000 0.05090 0.03697 = 0.03745 -0.00386 0.01227 -0.00078 C26 1 0.904592 0.863223 0.570528 11.00000 0.04443 0.03529 = 0.03667 -0.00159 0.01166 -0.00254 C27 1 0.852023 0.963856 0.499088 11.00000 0.04862 0.03533 = 0.04138 -0.00354 0.01319 -0.00170 H28 2 0.777641 1.118948 0.491312 11.00000 0.08385 O28 4 0.801268 1.060389 0.531644 11.00000 0.09991 0.04803 = 0.04336 0.00148 0.01873 0.02856 O29 4 0.858242 0.956300 0.420423 11.00000 0.07544 0.04878 = 0.04031 0.00598 0.02238 0.00996 N30 3 0.928723 0.700627 0.453137 11.00000 0.06946 0.04199 = 0.04416 -0.00609 0.01580 0.00544 O31 4 1.010195 0.700313 0.419848 11.00000 0.08594 0.15245 = 0.06979 -0.03233 0.03921 0.00597 O32 4 0.832636 0.662694 0.412830 11.00000 0.09499 0.09901 = 0.04734 -0.01627 0.00985 -0.02919 HKLF 4 REM mo_SEL_LC_6A_AcN_P21c_0m_a.res in P2(1)/n REM R1 = 0.0366 for 2530 Fo > 4sig(Fo) and 0.0464 for all 3077 data REM 277 parameters refined using 6 restraints END WGHT 0.0495 0.3494 REM Highest difference peak 0.210, deepest hole -0.210, 1-sigma level 0.042 Q1 1 1.0091 0.7962 0.4143 11.00000 0.05 0.21 Q2 1 0.4240 0.7234 0.4499 11.00000 0.05 0.19 Q3 1 0.9488 0.8190 0.5608 11.00000 0.05 0.13 Q4 1 0.5825 0.6847 0.5781 11.00000 0.05 0.12 Q5 1 0.8785 1.0950 0.5334 11.00000 0.05 0.12 ; _shelx_res_checksum 52270 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_posn _atom_site_occupancy C C1 0.69431(14) 0.61853(16) 0.68141(11) 0.0484(4) Uani d . . 1 H H1 0.7365 0.5401 0.6976 0.058 Uiso calc U R 1 C C2 0.68124(15) 0.70385(17) 0.74946(11) 0.0545(4) Uani d . . 1 H H2 0.7162 0.6837 0.8107 0.065 Uiso calc U R 1 C C3 0.61704(15) 0.81830(17) 0.72756(11) 0.0537(4) Uani d . . 1 H H3 0.6061 0.8741 0.774 0.064 Uiso calc U R 1 C C4 0.56882(14) 0.85062(16) 0.63724(11) 0.0508(4) Uani d . . 1 H H4 0.5259 0.9287 0.6218 0.061 Uiso calc U R 1 C C5 0.58482(12) 0.76574(14) 0.56972(10) 0.0402(3) Uani d . . 1 C C6 0.64605(12) 0.64666(14) 0.58906(10) 0.0396(3) Uani d . . 1 C C7 0.65220(12) 0.54931(14) 0.51610(10) 0.0409(3) Uani d . . 1 O O8 0.73094(11) 0.45639(12) 0.54510(8) 0.0631(4) Uani d . D 1 H H8 0.7259(19) 0.3995(18) 0.5034(11) 0.088(7) Uiso d . D 1 O O9 0.58941(9) 0.55410(10) 0.43895(7) 0.0508(3) Uani d . . 1 N N10 0.53872(12) 0.81129(13) 0.47483(9) 0.0495(3) Uani d . . 1 O O11 0.60807(12) 0.84580(13) 0.43288(8) 0.0690(4) Uani d . . 1 O O12 0.43428(12) 0.81768(19) 0.44412(10) 0.0941(5) Uani d . . 1 C C13 0.69983(13) 0.26442(16) 0.33986(11) 0.0462(4) Uani d . . 1 O O14 0.73122(10) 0.26453(11) 0.42612(7) 0.0543(3) Uani d . . 1 N N15 0.65153(15) 0.37302(16) 0.29458(11) 0.0608(4) Uani d . D 1 H H15A 0.6298(16) 0.4379(16) 0.3266(12) 0.074(6) Uiso d . D 1 H H15B 0.6263(16) 0.371(2) 0.2350(7) 0.070(6) Uiso d . D 1 N N16 0.71443(15) 0.15682(16) 0.29326(10) 0.0620(4) Uani d . D 1 H H16A 0.6983(16) 0.157(2) 0.2328(7) 0.073(6) Uiso d . D 1 H H16B 0.7579(14) 0.0905(15) 0.3219(12) 0.070(6) Uiso d . D 1 C C21 0.92104(14) 0.89027(16) 0.66328(10) 0.0478(4) Uani d . . 1 H H21 0.8944 0.9707 0.6809 0.057 Uiso calc U R 1 C C22 0.97570(15) 0.80121(18) 0.72981(11) 0.0554(4) Uani d . . 1 H H22 0.9849 0.8214 0.7915 0.067 Uiso calc U R 1 C C23 1.01668(16) 0.68280(18) 0.70549(12) 0.0606(5) Uani d . . 1 H H23 1.0541 0.623 0.7507 0.073 Uiso calc U R 1 C C24 1.00265(16) 0.65223(17) 0.61456(12) 0.0571(4) Uani d . . 1 H H24 1.0307 0.5721 0.5976 0.069 Uiso calc U R 1 C C25 0.94637(13) 0.74183(14) 0.54872(10) 0.0416(3) Uani d . . 1 C C26 0.90459(12) 0.86322(14) 0.57053(10) 0.0386(3) Uani d . . 1 C C27 0.85202(12) 0.96386(14) 0.49909(10) 0.0415(3) Uani d . . 1 H H28 0.7776(18) 1.1189(17) 0.4913(11) 0.084(7) Uiso d . D 1 O O28 0.80127(12) 1.06039(12) 0.53164(8) 0.0637(4) Uani d . D 1 O O29 0.85824(10) 0.95630(11) 0.42042(7) 0.0535(3) Uani d . . 1 N N30 0.92872(13) 0.70063(13) 0.45314(9) 0.0517(4) Uani d . . 1 O O31 1.01019(14) 0.70031(19) 0.41985(11) 0.0992(6) Uani d . . 1 O O32 0.83264(13) 0.66269(16) 0.41283(9) 0.0820(4) Uani d . . 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0558(9) 0.0432(9) 0.0423(8) 0.0005(7) 0.0056(7) 0.0070(7) C2 0.0657(10) 0.0583(11) 0.0362(8) -0.0147(8) 0.0068(7) 0.0003(7) C3 0.0713(10) 0.0481(10) 0.0458(9) -0.0122(8) 0.0223(8) -0.0107(8) C4 0.0638(9) 0.0391(9) 0.0523(10) 0.0005(7) 0.0198(8) -0.0016(7) C5 0.0461(7) 0.0369(8) 0.0376(8) -0.0017(6) 0.0106(6) 0.0025(6) C6 0.0432(7) 0.0347(8) 0.0398(8) -0.0030(6) 0.0087(6) 0.0016(6) C7 0.0463(8) 0.0329(8) 0.0423(8) -0.0003(6) 0.0091(7) 0.0035(6) O8 0.0815(8) 0.0483(7) 0.0509(7) 0.0245(6) 0.0012(6) -0.0058(6) O9 0.0619(7) 0.0442(6) 0.0415(6) 0.0049(5) 0.0047(5) -0.0031(5) N10 0.0614(8) 0.0415(8) 0.0441(8) 0.0085(6) 0.0108(7) 0.0027(6) O11 0.0885(9) 0.0704(9) 0.0491(7) -0.0132(7) 0.0200(7) 0.0110(6) O12 0.0615(8) 0.1477(16) 0.0669(9) 0.0327(9) 0.0054(7) 0.0240(9) C13 0.0491(8) 0.0451(9) 0.0428(9) 0.0021(7) 0.0094(7) 0.0018(7) O14 0.0751(7) 0.0455(7) 0.0405(6) 0.0159(5) 0.0116(5) 0.0006(5) N15 0.0799(10) 0.0533(9) 0.0443(9) 0.0134(8) 0.0073(8) 0.0072(7) N16 0.0848(10) 0.0572(10) 0.0396(8) 0.0172(8) 0.0078(8) -0.0044(7) C21 0.0636(9) 0.0419(9) 0.0396(8) 0.0005(7) 0.0164(7) -0.0056(7) C22 0.0741(11) 0.0560(11) 0.0347(8) -0.0029(8) 0.0113(8) 0.0012(7) C23 0.0784(11) 0.0532(11) 0.0457(10) 0.0070(9) 0.0079(9) 0.0104(8) C24 0.0755(11) 0.0402(9) 0.0541(10) 0.0122(8) 0.0140(8) 0.0002(8) C25 0.0509(8) 0.0370(8) 0.0375(8) -0.0008(6) 0.0123(6) -0.0039(6) C26 0.0444(7) 0.0353(8) 0.0367(8) -0.0025(6) 0.0117(6) -0.0016(6) C27 0.0486(8) 0.0353(8) 0.0414(9) -0.0017(6) 0.0132(6) -0.0035(6) O28 0.0999(9) 0.0480(7) 0.0434(7) 0.0286(7) 0.0187(6) 0.0015(5) O29 0.0754(7) 0.0488(7) 0.0403(6) 0.0100(5) 0.0224(5) 0.0060(5) N30 0.0695(9) 0.0420(8) 0.0442(8) 0.0054(6) 0.0158(7) -0.0061(6) O31 0.0859(10) 0.1525(17) 0.0698(10) 0.0060(10) 0.0392(8) -0.0323(10) O32 0.0950(10) 0.0990(11) 0.0473(7) -0.0292(9) 0.0098(7) -0.0163(7) 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 C2 C1 C6 121.58(15) C2 C1 H1 119.2 C6 C1 H1 119.2 C3 C2 C1 120.32(15) C3 C2 H2 119.8 C1 C2 H2 119.8 C2 C3 C4 120.01(16) C2 C3 H3 120.0 C4 C3 H3 120.0 C3 C4 C5 119.03(16) C3 C4 H4 120.5 C5 C4 H4 120.5 C4 C5 C6 122.76(14) C4 C5 N10 116.11(13) C6 C5 N10 121.05(13) C5 C6 C1 116.24(14) C5 C6 C7 122.20(13) C1 C6 C7 121.39(13) O9 C7 O8 123.82(14) O9 C7 C6 123.37(13) O8 C7 C6 112.79(12) C7 O8 H8 109.1(15) O12 N10 O11 123.48(15) O12 N10 C5 118.56(14) O11 N10 C5 117.89(13) O14 C13 N16 120.35(14) O14 C13 N15 120.11(15) N16 C13 N15 119.53(15) C13 N15 H15A 117.9(13) C13 N15 H15B 119.8(13) H15A N15 H15B 120.5(19) C13 N16 H16A 121.6(13) C13 N16 H16B 119.7(13) H16A N16 H16B 116.8(18) C22 C21 C26 121.66(15) C22 C21 H21 119.2 C26 C21 H21 119.2 C23 C22 C21 120.15(15) C23 C22 H22 119.9 C21 C22 H22 119.9 C22 C23 C24 120.12(16) C22 C23 H23 119.9 C24 C23 H23 119.9 C23 C24 C25 119.01(16) C23 C24 H24 120.5 C25 C24 H24 120.5 C24 C25 C26 122.63(14) C24 C25 N30 116.42(14) C26 C25 N30 120.91(13) C25 C26 C21 116.43(13) C25 C26 C27 122.19(13) C21 C26 C27 121.26(13) O29 C27 O28 124.56(14) O29 C27 C26 123.10(13) O28 C27 C26 112.33(13) C27 O28 H28 110.4(15) O31 N30 O32 123.08(15) O31 N30 C25 119.25(14) O32 N30 C25 117.58(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.374(2) C1 C6 1.389(2) C1 H1 0.93 C2 C3 1.369(2) C2 H2 0.93 C3 C4 1.371(2) C3 H3 0.93 C4 C5 1.376(2) C4 H4 0.93 C5 C6 1.389(2) C5 N10 1.4650(19) C6 C7 1.486(2) C7 O9 1.2075(17) C7 O8 1.3105(18) O8 H8 0.839(10) N10 O12 1.2035(18) N10 O11 1.2078(18) C13 O14 1.2555(19) C13 N16 1.323(2) C13 N15 1.333(2) N15 H15A 0.887(9) N15 H15B 0.870(9) N16 H16A 0.880(9) N16 H16B 0.882(9) C21 C22 1.373(2) C21 C26 1.387(2) C21 H21 0.93 C22 C23 1.368(3) C22 H22 0.93 C23 C24 1.371(2) C23 H23 0.93 C24 C25 1.376(2) C24 H24 0.93 C25 C26 1.386(2) C25 N30 1.460(2) C26 C27 1.489(2) C27 O29 1.2081(17) C27 O28 1.3003(18) O28 H28 0.839(10) N30 O31 1.1952(19) N30 O32 1.2035(19) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O8 H8 O14 . 0.839(10) 1.798(10) 2.6307(16) 172.(2) N15 H15A O9 . 0.887(9) 2.206(11) 3.065(2) 162.9(18) N15 H15B O29 2_645 0.870(9) 2.542(13) 3.3170(19) 148.8(17) N16 H16A O32 2_645 0.880(9) 2.130(10) 3.009(2) 177.1(19) N16 H16B O29 1_545 0.882(9) 2.125(11) 2.9879(19) 165.8(18) O28 H28 O14 1_565 0.839(10) 1.767(11) 2.5940(16) 168.(2) 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 C6 C1 C2 C3 1.7(2) C1 C2 C3 C4 -2.3(3) C2 C3 C4 C5 0.8(2) C3 C4 C5 C6 1.3(2) C3 C4 C5 N10 -175.47(14) C4 C5 C6 C1 -1.9(2) N10 C5 C6 C1 174.75(13) C4 C5 C6 C7 173.48(14) N10 C5 C6 C7 -9.9(2) C2 C1 C6 C5 0.4(2) C2 C1 C6 C7 -175.04(14) C5 C6 C7 O9 -13.5(2) C1 C6 C7 O9 161.62(15) C5 C6 C7 O8 167.97(14) C1 C6 C7 O8 -16.9(2) C4 C5 N10 O12 -69.0(2) C6 C5 N10 O12 114.14(18) C4 C5 N10 O11 107.93(17) C6 C5 N10 O11 -68.92(19) C26 C21 C22 C23 0.7(3) C21 C22 C23 C24 -0.4(3) C22 C23 C24 C25 -0.4(3) C23 C24 C25 C26 1.0(3) C23 C24 C25 N30 -176.90(16) C24 C25 C26 C21 -0.8(2) N30 C25 C26 C21 177.07(14) C24 C25 C26 C27 175.20(15) N30 C25 C26 C27 -7.0(2) C22 C21 C26 C25 -0.1(2) C22 C21 C26 C27 -176.09(15) C25 C26 C27 O29 -11.7(2) C21 C26 C27 O29 164.06(15) C25 C26 C27 O28 169.41(14) C21 C26 C27 O28 -14.8(2) C24 C25 N30 O31 -74.5(2) C26 C25 N30 O31 107.57(19) C24 C25 N30 O32 102.28(19) C26 C25 N30 O32 -75.7(2)