#------------------------------------------------------------------------------ #$Date: 2023-11-02 01:42:08 +0200 (Thu, 02 Nov 2023) $ #$Revision: 287231 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247643.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_7247643 loop_ _publ_author_name 'Wu, Qiong' 'Chai, Yingying' 'Huang, Ridong' 'Chen, Hai' 'He, Yang' _publ_section_title ; A linear CH+-NO3− Base Pair Motif promoted by AgNO3 mediated Proton Transferring between Guanosine and Cytidine ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00916E _journal_year 2023 _chemical_absolute_configuration ad _chemical_formula_moiety 'C9 H14 N3 O5, N O3' _chemical_formula_sum 'C9 H14 N4 O8' _chemical_formula_weight 306.24 _chemical_name_systematic 'N3-protonated Cytidine nitrate' _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2021-03-02 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2022-02-07 deposited with the CCDC. 2023-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.44(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.7120(15) _cell_length_b 7.4810(15) _cell_length_c 11.062(2) _cell_measurement_reflns_used 1531 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.85 _cell_measurement_theta_min 1.941 _cell_volume 605.4(2) _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_unetI/netI 0.0204 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_number 1531 _diffrn_reflns_point_group_measured_fraction_full 0.537 _diffrn_reflns_point_group_measured_fraction_max 0.534 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.840 _diffrn_reflns_theta_min 1.941 _exptl_absorpt_coefficient_mu 0.149 _exptl_crystal_colour 'dull dark black' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary black _exptl_crystal_density_diffrn 1.680 _exptl_crystal_description plate _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.222 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details ; No quotients, so Flack parameter determined by classical intensity fit ; _refine_ls_abs_structure_Flack 0.0(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 1531 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0311 _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^)+(0.0587P)^2^+0.1602P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0838 _refine_ls_wR_factor_ref 0.0843 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full 0.000 _reflns_Friedel_fraction_max 0.000 _reflns_number_gt 1510 _reflns_number_total 1531 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00916e2.cif _cod_data_source_block output _cod_database_code 7247643 _shelx_shelxl_version_number 2018/3 _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 0.997 _shelx_estimated_absorpt_t_min 0.985 _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 N(H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C7(H7), C6(H6), C8(H8), C5(H5) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C3(H3) 2.d Idealised tetrahedral OH refined as rotating group: O14(H14), O17(H17), O16(H16), N10(H10A) ; _shelx_res_file ; TITL output_a.res in P2(1) output.res created by SHELXL-2018/3 at 10:43:24 on 02-Mar-2021 REM Old TITL output_a.res in P2(1) REM SHELXT solution in P2(1): R1 0.069, Rweak 0.032, Alpha 0.003 REM 3.224 for 4 systematic absences, Orientation as input REM Formula found by SHELXT: C9 N3 O9 CELL 0.71073 7.712 7.481 11.062 90 108.441 90 ZERR 2 0.0015 0.0015 0.0022 0 0.03 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 18 28 8 16 L.S. 10 PLAN 7 SIZE 0.02 0.03 0.1 TEMP -173.15 CONF BOND list 4 MORE -1 BOND $H fmap 2.0 ACTA REM REM REM WGHT 0.058700 0.160200 FVAR 1.90174 O15 4 -0.536242 -0.306047 -0.791621 11.00000 0.01538 0.01104 = 0.01492 0.00233 0.00456 -0.00229 O13 4 -0.689094 -0.736685 -0.625282 11.00000 0.02647 0.01163 = 0.01449 0.00091 0.00916 0.00007 O14 4 -0.679631 -0.637749 -0.949283 11.00000 0.02392 0.01204 = 0.01524 -0.00173 0.00752 0.00440 AFIX 147 H14 2 -0.744373 -0.641277 -1.026228 11.00000 -1.50000 AFIX 0 O19 4 -0.836538 -0.864991 -0.386602 11.00000 0.02519 0.01639 = 0.01126 -0.00153 0.00883 -0.00096 O17 4 -0.749679 0.013321 -0.833425 11.00000 0.02370 0.01065 = 0.01691 -0.00174 0.00698 -0.00048 AFIX 147 H17 2 -0.707904 0.111158 -0.799211 11.00000 -1.50000 AFIX 0 O16 4 -0.895281 -0.367103 -1.084559 11.00000 0.01942 0.01555 = 0.01180 -0.00050 0.00483 -0.00223 AFIX 147 H16 2 -1.003973 -0.402466 -1.103349 11.00000 -1.50000 AFIX 0 O20 4 -0.861079 -0.723927 -0.220262 11.00000 0.02410 0.01585 = 0.01668 -0.00320 0.00909 0.00114 O21 4 -0.875183 -1.013740 -0.229470 11.00000 0.03625 0.01655 = 0.02029 0.00265 0.01400 -0.00142 N11 3 -0.750511 -0.553219 -0.479131 11.00000 0.02222 0.01205 = 0.01254 0.00271 0.00731 -0.00112 N18 3 -0.856729 -0.867978 -0.277837 11.00000 0.01523 0.01623 = 0.01287 0.00033 0.00474 -0.00027 N12 3 -0.674439 -0.434432 -0.650886 11.00000 0.01782 0.01212 = 0.01179 0.00060 0.00619 -0.00042 N10 3 -0.820692 -0.375858 -0.330882 11.00000 0.02860 0.01869 = 0.01460 -0.00007 0.01073 0.00129 AFIX 147 H10A 2 -0.835300 -0.478698 -0.305193 11.00000 -1.50000 AFIX 0 C7 1 -0.821297 -0.346135 -0.950526 11.00000 0.01598 0.01092 = 0.01177 -0.00011 0.00695 0.00026 AFIX 13 H7 2 -0.909502 -0.281880 -0.916306 11.00000 -1.20000 AFIX 0 C2 1 -0.703450 -0.585127 -0.588409 11.00000 0.01641 0.01415 = 0.01216 0.00148 0.00438 -0.00022 C6 1 -0.763407 -0.523807 -0.880858 11.00000 0.01714 0.01139 = 0.01308 0.00067 0.00634 -0.00092 AFIX 13 H6 2 -0.865691 -0.583778 -0.859243 11.00000 -1.20000 AFIX 0 C8 1 -0.640360 -0.244555 -0.918070 11.00000 0.01654 0.01076 = 0.01263 0.00204 0.00667 0.00080 AFIX 13 H8 2 -0.575186 -0.281801 -0.979061 11.00000 -1.20000 AFIX 0 C5 1 -0.608706 -0.466053 -0.762595 11.00000 0.01693 0.01116 = 0.01299 0.00108 0.00693 0.00001 AFIX 13 H5 2 -0.511395 -0.559919 -0.740478 11.00000 -1.20000 AFIX 0 C9 1 -0.648385 -0.043051 -0.916166 11.00000 0.02250 0.01247 = 0.01712 0.00207 0.00923 -0.00178 AFIX 23 H9A 2 -0.522967 0.006413 -0.885306 11.00000 -1.20000 H9B 2 -0.708496 0.002426 -1.003470 11.00000 -1.20000 AFIX 0 C4 1 -0.754020 -0.237464 -0.507546 11.00000 0.02031 0.01243 = 0.01480 -0.00176 0.00518 0.00041 AFIX 43 H4 2 -0.774613 -0.119838 -0.482727 11.00000 -1.20000 AFIX 0 C1 1 -0.776580 -0.388522 -0.436132 11.00000 0.01647 0.01730 = 0.01386 -0.00148 0.00396 -0.00023 C3 1 -0.702321 -0.266161 -0.611976 11.00000 0.01708 0.01226 = 0.01514 -0.00036 0.00453 -0.00181 AFIX 43 H3 2 -0.684795 -0.166284 -0.659867 11.00000 -1.20000 AFIX 0 H10B 2 -0.840637 -0.259251 -0.298099 11.00000 0.04551 H11 2 -0.771769 -0.647679 -0.445336 11.00000 0.01832 HKLF 4 REM output_a.res in P2(1) REM wR2 = 0.084274, GooF = S = 1.07462, Restrained GooF = 1.07421 for all data REM R1 = 0.031090 for 1510 Fo > 4sig(Fo) and 0.031436 for all 1531 data REM 202 parameters refined using 1 restraints END WGHT 0.0589 0.1589 REM Highest difference peak 0.222, deepest hole -0.255, 1-sigma level 0.053 Q1 1 -0.7372 -0.5544 -0.5358 11.00000 0.05 0.22 Q2 1 -0.7330 -0.3118 -0.9290 11.00000 0.05 0.22 Q3 1 -0.7202 -0.2700 -0.5451 11.00000 0.05 0.21 Q4 1 -0.6884 -0.4985 -0.8169 11.00000 0.05 0.20 Q5 1 -0.7936 -0.5879 -0.2438 11.00000 0.05 0.18 Q6 1 -1.0844 -0.9034 -0.3383 11.00000 0.05 0.18 Q7 1 -0.7794 -0.4423 -0.9138 11.00000 0.05 0.18 ; _shelx_res_checksum 48169 _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O15 O -0.53624(18) -0.30605(19) -0.79162(12) 0.0138(3) Uani 1 1 d . . . . . O13 O -0.6891(2) -0.7367(2) -0.62528(13) 0.0169(3) Uani 1 1 d . . . . . O14 O -0.6796(2) -0.6377(2) -0.94928(13) 0.0168(3) Uani 1 1 d . . . . . H14 H -0.744373 -0.641277 -1.026228 0.025 Uiso 1 1 calc R U . . . O19 O -0.83654(19) -0.8650(2) -0.38660(12) 0.0169(3) Uani 1 1 d . . . . . O17 O -0.74968(19) 0.0133(2) -0.83342(13) 0.0170(3) Uani 1 1 d . . . . . H17 H -0.707904 0.111158 -0.799211 0.025 Uiso 1 1 calc R U . . . O16 O -0.89528(18) -0.3671(2) -1.08456(11) 0.0156(3) Uani 1 1 d . . . . . H16 H -1.003973 -0.402466 -1.103349 0.023 Uiso 1 1 calc R U . . . O20 O -0.8611(2) -0.7239(2) -0.22026(14) 0.0183(3) Uani 1 1 d . . . . . O21 O -0.8752(2) -1.0137(2) -0.22947(15) 0.0232(3) Uani 1 1 d . . . . . N11 N -0.7505(2) -0.5532(2) -0.47913(16) 0.0152(3) Uani 1 1 d . . . . . N18 N -0.8567(2) -0.8680(3) -0.27784(15) 0.0147(3) Uani 1 1 d . . . . . N12 N -0.6744(2) -0.4344(2) -0.65089(15) 0.0136(3) Uani 1 1 d . . . . . N10 N -0.8207(3) -0.3759(3) -0.33088(16) 0.0197(4) Uani 1 1 d . . . . . H10A H -0.835300 -0.478698 -0.305193 0.030 Uiso 1 1 calc R U . . . C7 C -0.8213(2) -0.3461(3) -0.95053(16) 0.0123(3) Uani 1 1 d . . . . . H7 H -0.909502 -0.281880 -0.916306 0.015 Uiso 1 1 calc R U . . . C2 C -0.7035(3) -0.5851(3) -0.58841(18) 0.0143(4) Uani 1 1 d . . . . . C6 C -0.7634(2) -0.5238(3) -0.88086(16) 0.0135(4) Uani 1 1 d . . . . . H6 H -0.865691 -0.583778 -0.859243 0.016 Uiso 1 1 calc R U . . . C8 C -0.6404(2) -0.2446(3) -0.91807(17) 0.0128(3) Uani 1 1 d . . . . . H8 H -0.575186 -0.281801 -0.979061 0.015 Uiso 1 1 calc R U . . . C5 C -0.6087(3) -0.4661(3) -0.76260(17) 0.0132(3) Uani 1 1 d . . . . . H5 H -0.511395 -0.559919 -0.740478 0.016 Uiso 1 1 calc R U . . . C9 C -0.6484(3) -0.0431(3) -0.91617(19) 0.0167(4) Uani 1 1 d . . . . . H9A H -0.522967 0.006413 -0.885306 0.020 Uiso 1 1 calc R U . . . H9B H -0.708496 0.002426 -1.003470 0.020 Uiso 1 1 calc R U . . . C4 C -0.7540(3) -0.2375(3) -0.50755(18) 0.0159(4) Uani 1 1 d . . . . . H4 H -0.774613 -0.119838 -0.482727 0.019 Uiso 1 1 calc R U . . . C1 C -0.7766(2) -0.3885(3) -0.43613(18) 0.0161(4) Uani 1 1 d . . . . . C3 C -0.7023(3) -0.2662(3) -0.61198(18) 0.0150(4) Uani 1 1 d . . . . . H3 H -0.684795 -0.166284 -0.659867 0.018 Uiso 1 1 calc R U . . . H10B H -0.841(5) -0.259(7) -0.298(4) 0.046(10) Uiso 1 1 d . . . . . H11 H -0.772(4) -0.648(5) -0.445(3) 0.018(7) 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 O15 0.0154(6) 0.0110(6) 0.0149(6) 0.0023(5) 0.0046(5) -0.0023(5) O13 0.0265(7) 0.0116(7) 0.0145(6) 0.0009(5) 0.0092(6) 0.0001(6) O14 0.0239(7) 0.0120(6) 0.0152(6) -0.0017(5) 0.0075(5) 0.0044(6) O19 0.0252(6) 0.0164(7) 0.0113(6) -0.0015(5) 0.0088(5) -0.0010(6) O17 0.0237(7) 0.0107(6) 0.0169(6) -0.0017(5) 0.0070(5) -0.0005(5) O16 0.0194(6) 0.0156(7) 0.0118(6) -0.0005(5) 0.0048(5) -0.0022(6) O20 0.0241(7) 0.0158(7) 0.0167(6) -0.0032(6) 0.0091(6) 0.0011(6) O21 0.0362(9) 0.0166(8) 0.0203(7) 0.0027(6) 0.0140(6) -0.0014(7) N11 0.0222(8) 0.0121(8) 0.0125(7) 0.0027(6) 0.0073(6) -0.0011(6) N18 0.0152(7) 0.0162(8) 0.0129(7) 0.0003(6) 0.0047(5) -0.0003(7) N12 0.0178(7) 0.0121(8) 0.0118(7) 0.0006(6) 0.0062(5) -0.0004(6) N10 0.0286(8) 0.0187(9) 0.0146(7) -0.0001(7) 0.0107(6) 0.0013(7) C7 0.0160(7) 0.0109(8) 0.0118(7) -0.0001(6) 0.0070(6) 0.0003(6) C2 0.0164(8) 0.0142(9) 0.0122(8) 0.0015(7) 0.0044(6) -0.0002(7) C6 0.0171(8) 0.0114(8) 0.0131(8) 0.0007(7) 0.0063(6) -0.0009(7) C8 0.0165(8) 0.0108(8) 0.0126(8) 0.0020(6) 0.0067(6) 0.0008(7) C5 0.0169(8) 0.0112(8) 0.0130(7) 0.0011(6) 0.0069(6) 0.0000(7) C9 0.0225(9) 0.0125(9) 0.0171(8) 0.0021(7) 0.0092(7) -0.0018(7) C4 0.0203(9) 0.0124(9) 0.0148(8) -0.0018(7) 0.0052(7) 0.0004(7) C1 0.0165(8) 0.0173(10) 0.0139(8) -0.0015(7) 0.0040(6) -0.0002(7) C3 0.0171(8) 0.0123(9) 0.0151(8) -0.0004(7) 0.0045(7) -0.0018(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O15 C8 110.67(14) . . ? C6 O14 H14 109.5 . . ? C9 O17 H17 109.5 . . ? C7 O16 H16 109.5 . . ? C2 N11 H11 113(2) . . ? C1 N11 C2 124.70(17) . . ? C1 N11 H11 122(2) . . ? O20 N18 O19 119.94(17) . . ? O21 N18 O19 119.46(17) . . ? O21 N18 O20 120.59(14) . . ? C2 N12 C5 115.89(16) . . ? C3 N12 C2 121.89(16) . . ? C3 N12 C5 122.22(16) . . ? H10A N10 H10B 129.8 . . ? C1 N10 H10A 109.5 . . ? C1 N10 H10B 121(2) . . ? O16 C7 H7 110.6 . . ? O16 C7 C6 112.77(15) . . ? O16 C7 C8 109.62(14) . . ? C6 C7 H7 110.6 . . ? C8 C7 H7 110.6 . . ? C8 C7 C6 102.37(14) . . ? O13 C2 N11 121.77(18) . . ? O13 C2 N12 123.08(17) . . ? N12 C2 N11 115.15(17) . . ? O14 C6 C7 111.19(14) . . ? O14 C6 H6 112.6 . . ? O14 C6 C5 105.18(15) . . ? C7 C6 H6 112.6 . . ? C5 C6 C7 102.12(15) . . ? C5 C6 H6 112.6 . . ? O15 C8 C7 104.75(14) . . ? O15 C8 H8 108.6 . . ? O15 C8 C9 108.43(17) . . ? C7 C8 H8 108.6 . . ? C9 C8 C7 117.48(17) . . ? C9 C8 H8 108.6 . . ? O15 C5 N12 108.56(15) . . ? O15 C5 C6 107.79(14) . . ? O15 C5 H5 109.5 . . ? N12 C5 C6 112.04(15) . . ? N12 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? O17 C9 C8 109.51(16) . . ? O17 C9 H9A 109.8 . . ? O17 C9 H9B 109.8 . . ? C8 C9 H9A 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C1 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C3 C4 C1 118.00(19) . . ? N11 C1 C4 117.97(17) . . ? N10 C1 N11 118.92(19) . . ? N10 C1 C4 123.11(19) . . ? N12 C3 H3 118.9 . . ? C4 C3 N12 122.16(19) . . ? C4 C3 H3 118.9 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O15 C8 1.450(2) . ? O15 C5 1.401(2) . ? O13 C2 1.222(3) . ? O14 H14 0.8400 . ? O14 C6 1.423(2) . ? O19 N18 1.261(2) . ? O17 H17 0.8400 . ? O17 C9 1.442(2) . ? O16 H16 0.8400 . ? O16 C7 1.419(2) . ? O20 N18 1.258(2) . ? O21 N18 1.242(2) . ? N11 C2 1.388(2) . ? N11 C1 1.358(3) . ? N11 H11 0.84(3) . ? N12 C2 1.377(2) . ? N12 C5 1.495(2) . ? N12 C3 1.369(3) . ? N10 H10A 0.8400 . ? N10 C1 1.316(2) . ? N10 H10B 0.98(5) . ? C7 H7 1.0000 . ? C7 C6 1.530(3) . ? C7 C8 1.529(3) . ? C6 H6 1.0000 . ? C6 C5 1.528(3) . ? C8 H8 1.0000 . ? C8 C9 1.509(3) . ? C5 H5 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C4 H4 0.9500 . ? C4 C1 1.421(3) . ? C4 C3 1.353(3) . ? C3 H3 0.9500 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O15 C8 C9 O17 -64.9(2) . . . . ? O14 C6 C5 O15 91.79(17) . . . . ? O14 C6 C5 N12 -148.82(15) . . . . ? O16 C7 C6 O14 39.7(2) . . . . ? O16 C7 C6 C5 151.43(14) . . . . ? O16 C7 C8 O15 -152.02(14) . . . . ? O16 C7 C8 C9 87.6(2) . . . . ? C7 C6 C5 O15 -24.40(18) . . . . ? C7 C6 C5 N12 94.99(17) . . . . ? C7 C8 C9 O17 53.5(2) . . . . ? C2 N11 C1 N10 -179.90(18) . . . . ? C2 N11 C1 C4 -0.1(3) . . . . ? C2 N12 C5 O15 -163.01(15) . . . . ? C2 N12 C5 C6 78.1(2) . . . . ? C2 N12 C3 C4 2.3(3) . . . . ? C6 C7 C8 O15 -32.10(17) . . . . ? C6 C7 C8 C9 -152.45(17) . . . . ? C8 O15 C5 N12 -117.21(16) . . . . ? C8 O15 C5 C6 4.36(19) . . . . ? C8 C7 C6 O14 -78.02(17) . . . . ? C8 C7 C6 C5 33.72(16) . . . . ? C5 O15 C8 C7 17.76(18) . . . . ? C5 O15 C8 C9 143.96(16) . . . . ? C5 N12 C2 O13 -4.8(3) . . . . ? C5 N12 C2 N11 175.15(16) . . . . ? C5 N12 C3 C4 -177.01(16) . . . . ? C1 N11 C2 O13 -176.95(19) . . . . ? C1 N11 C2 N12 3.1(3) . . . . ? C1 C4 C3 N12 1.0(3) . . . . ? C3 N12 C2 O13 175.92(19) . . . . ? C3 N12 C2 N11 -4.2(3) . . . . ? C3 N12 C5 O15 16.3(2) . . . . ? C3 N12 C5 C6 -102.6(2) . . . . ? C3 C4 C1 N11 -2.0(3) . . . . ? C3 C4 C1 N10 177.76(18) . . . . ?