#------------------------------------------------------------------------------ #$Date: 2022-01-06 23:47:18 +0200 (Thu, 06 Jan 2022) $ #$Revision: 271861 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061023.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_7061023 loop_ _publ_author_name 'Garc\'ia-Raso, Angel' 'Terr\'on, Angel' 'Fiol, Juan J.' 'L\'opez-Zafra, Adela' 'Massanet, B\'arbara' 'Frontera, Antonio' 'Barcel\'o-Oliver, Miquel' _publ_section_title ; Modified-amino acid/peptide pyrimidine analogs: synthesis, structural characterization and DFT studies of N-(pyrimidyl)gabapentine and N-(pyrimidyl)baclofen ; _journal_issue 47 _journal_name_full 'New Journal of Chemistry' _journal_page_first 22053 _journal_page_last 22061 _journal_paper_doi 10.1039/D1NJ04639J _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C14 H14 Cl N3 O2' _chemical_formula_sum 'C14 H14 Cl N3 O2' _chemical_formula_weight 291.73 _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' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-10-21 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-09-01 deposited with the CCDC. 2021-10-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.152(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.9144(5) _cell_length_b 8.5835(4) _cell_length_c 15.5150(6) _cell_measurement_reflns_used 9970 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 72.188 _cell_measurement_theta_min 4.566 _cell_volume 1426.06(11) _computing_cell_refinement 'Bruker Apex3, 2016' _computing_data_collection 'Bruker Apex3, 2016' _computing_data_reduction 'SAINT v8.40A (Bruker, 2019)' _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 273.15 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator multilayer _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_unetI/netI 0.0230 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 16820 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 66.590 _diffrn_reflns_theta_max 66.590 _diffrn_reflns_theta_min 4.566 _diffrn_source 'high brilliance microfocus sealed tube' _diffrn_source_current 1.2 _diffrn_source_power 0.06 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.422 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.5134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1165 before and 0.0630 after correction. The Ratio of minimum to maximum transmission is 0.6813. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.413 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2462 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0494 _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^)+(0.0723P)^2^+0.5573P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1347 _refine_ls_wR_factor_ref 0.1378 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2260 _reflns_number_total 2462 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04639j2.cif _cod_data_source_block 1_a _cod_depositor_comments 'Adding full bibliography for 7061023--7061024.cif.' _cod_database_code 7061023 _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 0.760 _shelx_estimated_absorpt_t_min 0.389 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Ternary CH refined with riding coordinates: C9(H9) 2.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: N7(H7), C6(H6), C19(H19), C15(H15), C5(H5), C4(H4), C18(H18), C16(H16) ; _shelx_res_file ; TITL 1_a.res in P2(1)/n 1_a.res created by SHELXL-2018/3 at 12:55:56 on 21-Oct-2020 REM Old TITL 1 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.222, Rweak 0.017, Alpha 0.047 REM 1.006 for 204 systematic absences, Orientation as input REM Formula found by SHELXT: C14 N4 O Cl CELL 1.54178 10.9144 8.5835 15.515 90 101.152 90 ZERR 4 0.0005 0.0004 0.0006 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Cl UNIT 56 56 12 8 4 EQIV $1 1.5-X,-0.5+Y,0.5-Z EQIV $2 1.5-X,0.5+Y,0.5-Z L.S. 10 PLAN 1 SIZE 0.12 0.21 0.48 TEMP 0 CONF HTAB O13 N1_$1 HTAB N7 O12_$2 BOND LIST 6 MORE -1 BOND $H fmap 2 acta SHEL 100 0.84 REM REM REM WGHT 0.072300 0.557300 FVAR 1.30793 CL20 5 0.293544 -0.167407 0.384182 11.00000 0.13060 0.10895 = 0.09618 0.00652 0.00686 -0.07049 O13 4 0.556129 0.401616 0.117010 11.00000 0.10689 0.08555 = 0.04506 -0.01444 -0.00169 0.03863 N1 3 0.911629 0.710194 0.509340 11.00000 0.06084 0.05284 = 0.04018 -0.00009 0.00742 -0.01210 O12 4 0.712069 0.284066 0.204005 11.00000 0.07576 0.11055 = 0.05071 -0.02166 0.00279 0.03293 N7 3 0.721829 0.612214 0.443041 11.00000 0.06305 0.06227 = 0.03954 0.00239 0.00722 -0.01634 AFIX 43 H7 2 0.720609 0.685221 0.404921 11.00000 -1.20000 AFIX 0 N3 3 0.819221 0.500780 0.574615 11.00000 0.06787 0.05678 = 0.04541 0.00548 0.01102 -0.01063 C2 1 0.820117 0.606077 0.510890 11.00000 0.05606 0.04640 = 0.03582 -0.00533 0.01191 -0.00500 C10 1 0.592333 0.470320 0.266027 11.00000 0.06833 0.04962 = 0.04357 -0.00484 0.01296 -0.00031 AFIX 23 H10A 2 0.503799 0.494028 0.252301 11.00000 -1.20000 H10B 2 0.637559 0.568134 0.269719 11.00000 -1.20000 AFIX 0 C11 1 0.625572 0.374271 0.192987 11.00000 0.05505 0.05247 = 0.04395 -0.00418 0.01105 -0.00264 C9 1 0.622517 0.388471 0.355470 11.00000 0.04987 0.05199 = 0.04307 -0.00300 0.00984 -0.00092 AFIX 13 H9 2 0.708106 0.348730 0.363024 11.00000 -1.20000 AFIX 0 C14 1 0.537325 0.250197 0.360584 11.00000 0.05214 0.05332 = 0.03847 -0.00484 0.00895 -0.00255 C8 1 0.618385 0.503562 0.430469 11.00000 0.05426 0.06366 = 0.04461 -0.00601 0.01542 -0.01001 AFIX 23 H8A 2 0.540564 0.561270 0.417754 11.00000 -1.20000 H8B 2 0.620149 0.445870 0.484455 11.00000 -1.20000 AFIX 0 C6 1 1.007221 0.708975 0.577505 11.00000 0.06264 0.06799 = 0.05021 -0.00062 0.00453 -0.01774 AFIX 43 H6 2 1.071779 0.779994 0.578295 11.00000 -1.20000 AFIX 0 C19 1 0.586941 0.103136 0.378277 11.00000 0.06060 0.05580 = 0.06763 0.00196 0.00428 -0.00113 AFIX 43 H19 2 0.672869 0.089583 0.385542 11.00000 -1.20000 AFIX 0 C15 1 0.409017 0.265857 0.350423 11.00000 0.05821 0.06260 = 0.06878 -0.00888 0.01499 -0.00103 AFIX 43 H15 2 0.373053 0.363711 0.338736 11.00000 -1.20000 AFIX 0 C5 1 1.014136 0.607547 0.646258 11.00000 0.06442 0.08189 = 0.04770 0.00685 -0.00089 -0.00636 AFIX 43 H5 2 1.080839 0.608293 0.693718 11.00000 -1.20000 AFIX 0 C4 1 0.916998 0.504843 0.641045 11.00000 0.07262 0.06803 = 0.04673 0.01133 0.00926 -0.00182 AFIX 43 H4 2 0.919374 0.433699 0.686548 11.00000 -1.20000 AFIX 0 C18 1 0.512535 -0.024405 0.385487 11.00000 0.09029 0.05621 = 0.07827 0.00733 0.00001 -0.00954 AFIX 43 H18 2 0.547973 -0.122485 0.397415 11.00000 -1.20000 AFIX 0 C17 1 0.386152 -0.004953 0.374899 11.00000 0.08304 0.07283 = 0.05279 -0.00272 0.01033 -0.02850 C16 1 0.333019 0.138791 0.357298 11.00000 0.05718 0.09225 = 0.07200 -0.01642 0.01820 -0.01693 AFIX 43 H16 2 0.246976 0.151137 0.350032 11.00000 -1.20000 AFIX 0 H13 2 0.577389 0.333293 0.073125 11.00000 0.12633 HKLF 4 REM 1_a.res in P2(1)/n REM wR2 = 0.137817, GooF = S = 1.02852, Restrained GooF = 1.02852 for all data REM R1 = 0.049352 for 2260 Fo > 4sig(Fo) and 0.052353 for all 2462 data REM 185 parameters refined using 0 restraints END WGHT 0.0723 0.5572 REM Highest difference peak 0.413, deepest hole -0.430, 1-sigma level 0.036 Q1 1 0.2301 -0.0726 0.3879 11.00000 0.05 0.41 ; _shelx_res_checksum 67702 _olex2_exptl_crystal_mounting_method cryoloop _olex2_submission_special_instructions 'No special instructions were received' 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_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 Cl20 Cl 0.29354(9) -0.16741(11) 0.38418(5) 0.1139(4) Uani 1 1 d . . . . . O13 O 0.55613(18) 0.4016(2) 0.11701(10) 0.0814(6) Uani 1 1 d . . . . . N1 N 0.91163(15) 0.71019(19) 0.50934(10) 0.0516(4) Uani 1 1 d . . . . . O12 O 0.71207(15) 0.2841(2) 0.20401(10) 0.0803(5) Uani 1 1 d . . . . . N7 N 0.72183(15) 0.6122(2) 0.44304(10) 0.0553(4) Uani 1 1 d . . . . . H7 H 0.720609 0.685221 0.404921 0.066 Uiso 1 1 calc R U . . . N3 N 0.81922(16) 0.5008(2) 0.57462(10) 0.0567(4) Uani 1 1 d . . . . . C2 C 0.82012(17) 0.6061(2) 0.51089(11) 0.0457(4) Uani 1 1 d . . . . . C10 C 0.5923(2) 0.4703(2) 0.26603(12) 0.0536(5) Uani 1 1 d . . . . . H10A H 0.503799 0.494028 0.252301 0.064 Uiso 1 1 calc R U . . . H10B H 0.637559 0.568134 0.269719 0.064 Uiso 1 1 calc R U . . . C11 C 0.62557(18) 0.3743(2) 0.19299(12) 0.0503(5) Uani 1 1 d . . . . . C9 C 0.62252(17) 0.3885(2) 0.35547(12) 0.0482(4) Uani 1 1 d . . . . . H9 H 0.708106 0.348730 0.363024 0.058 Uiso 1 1 calc R U . . . C14 C 0.53733(17) 0.2502(2) 0.36058(11) 0.0480(4) Uani 1 1 d . . . . . C8 C 0.61838(18) 0.5036(2) 0.43047(12) 0.0534(5) Uani 1 1 d . . . . . H8A H 0.540564 0.561270 0.417754 0.064 Uiso 1 1 calc R U . . . H8B H 0.620149 0.445870 0.484455 0.064 Uiso 1 1 calc R U . . . C6 C 1.0072(2) 0.7090(3) 0.57750(13) 0.0611(5) Uani 1 1 d . . . . . H6 H 1.071779 0.779994 0.578295 0.073 Uiso 1 1 calc R U . . . C19 C 0.5869(2) 0.1031(3) 0.37828(15) 0.0624(5) Uani 1 1 d . . . . . H19 H 0.672869 0.089583 0.385542 0.075 Uiso 1 1 calc R U . . . C15 C 0.4090(2) 0.2659(3) 0.35042(15) 0.0628(6) Uani 1 1 d . . . . . H15 H 0.373053 0.363711 0.338736 0.075 Uiso 1 1 calc R U . . . C5 C 1.0141(2) 0.6075(3) 0.64626(14) 0.0662(6) Uani 1 1 d . . . . . H5 H 1.080839 0.608293 0.693718 0.079 Uiso 1 1 calc R U . . . C4 C 0.9170(2) 0.5048(3) 0.64105(14) 0.0628(6) Uani 1 1 d . . . . . H4 H 0.919374 0.433699 0.686548 0.075 Uiso 1 1 calc R U . . . C18 C 0.5125(3) -0.0244(3) 0.38549(17) 0.0771(7) Uani 1 1 d . . . . . H18 H 0.547973 -0.122485 0.397415 0.093 Uiso 1 1 calc R U . . . C17 C 0.3862(2) -0.0050(3) 0.37490(15) 0.0699(7) Uani 1 1 d . . . . . C16 C 0.3330(2) 0.1388(3) 0.35730(16) 0.0730(7) Uani 1 1 d . . . . . H16 H 0.246976 0.151137 0.350032 0.088 Uiso 1 1 calc R U . . . H13 H 0.577(3) 0.333(5) 0.073(3) 0.126(12) 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 Cl20 0.1306(7) 0.1090(7) 0.0962(6) 0.0065(4) 0.0069(5) -0.0705(5) O13 0.1069(13) 0.0855(12) 0.0451(8) -0.0144(8) -0.0017(8) 0.0386(10) N1 0.0608(9) 0.0528(9) 0.0402(8) -0.0001(7) 0.0074(7) -0.0121(7) O12 0.0758(10) 0.1105(14) 0.0507(8) -0.0217(8) 0.0028(7) 0.0329(10) N7 0.0630(10) 0.0623(10) 0.0395(8) 0.0024(7) 0.0072(7) -0.0163(8) N3 0.0679(10) 0.0568(10) 0.0454(9) 0.0055(7) 0.0110(7) -0.0106(8) C2 0.0561(10) 0.0464(10) 0.0358(8) -0.0053(7) 0.0119(7) -0.0050(8) C10 0.0683(12) 0.0496(11) 0.0436(10) -0.0048(8) 0.0130(8) -0.0003(9) C11 0.0551(10) 0.0525(11) 0.0440(10) -0.0042(8) 0.0110(8) -0.0026(9) C9 0.0499(10) 0.0520(11) 0.0431(9) -0.0030(8) 0.0098(7) -0.0009(8) C14 0.0521(10) 0.0533(11) 0.0385(9) -0.0048(8) 0.0089(7) -0.0026(8) C8 0.0543(10) 0.0637(13) 0.0446(10) -0.0060(9) 0.0154(8) -0.0100(9) C6 0.0626(12) 0.0680(14) 0.0502(11) -0.0006(10) 0.0045(9) -0.0177(10) C19 0.0606(12) 0.0558(12) 0.0676(13) 0.0020(10) 0.0043(10) -0.0011(10) C15 0.0582(12) 0.0626(13) 0.0688(13) -0.0089(11) 0.0150(10) -0.0010(10) C5 0.0644(12) 0.0819(16) 0.0477(11) 0.0068(10) -0.0009(9) -0.0064(11) C4 0.0726(13) 0.0680(14) 0.0467(10) 0.0113(9) 0.0093(9) -0.0018(11) C18 0.0903(18) 0.0562(14) 0.0783(16) 0.0073(12) 0.0000(13) -0.0095(12) C17 0.0830(16) 0.0728(16) 0.0528(12) -0.0027(11) 0.0103(10) -0.0285(13) C16 0.0572(12) 0.0923(19) 0.0720(15) -0.0164(13) 0.0182(10) -0.0169(12) 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' Cl Cl 0.3639 0.7018 '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 C11 O13 H13 111(2) . . ? C6 N1 C2 116.78(17) . . ? C2 N7 H7 117.9 . . ? C2 N7 C8 124.11(17) . . ? C8 N7 H7 117.9 . . ? C4 N3 C2 115.69(17) . . ? N1 C2 N7 116.17(16) . . ? N3 C2 N1 124.95(17) . . ? N3 C2 N7 118.87(17) . . ? H10A C10 H10B 107.8 . . ? C11 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C11 C10 C9 112.99(17) . . ? C9 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? O13 C11 C10 113.80(18) . . ? O12 C11 O13 123.34(18) . . ? O12 C11 C10 122.80(18) . . ? C10 C9 H9 107.5 . . ? C10 C9 C8 111.03(16) . . ? C14 C9 C10 112.25(15) . . ? C14 C9 H9 107.5 . . ? C14 C9 C8 110.82(14) . . ? C8 C9 H9 107.5 . . ? C19 C14 C9 120.29(17) . . ? C19 C14 C15 117.4(2) . . ? C15 C14 C9 122.26(19) . . ? N7 C8 C9 112.36(15) . . ? N7 C8 H8A 109.1 . . ? N7 C8 H8B 109.1 . . ? C9 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? N1 C6 H6 118.7 . . ? N1 C6 C5 122.7(2) . . ? C5 C6 H6 118.7 . . ? C14 C19 H19 119.1 . . ? C14 C19 C18 121.8(2) . . ? C18 C19 H19 119.1 . . ? C14 C15 H15 119.3 . . ? C14 C15 C16 121.4(2) . . ? C16 C15 H15 119.3 . . ? C6 C5 H5 122.0 . . ? C6 C5 C4 116.01(19) . . ? C4 C5 H5 122.0 . . ? N3 C4 C5 123.88(19) . . ? N3 C4 H4 118.1 . . ? C5 C4 H4 118.1 . . ? C19 C18 H18 120.4 . . ? C17 C18 C19 119.3(2) . . ? C17 C18 H18 120.4 . . ? C18 C17 Cl20 118.7(2) . . ? C18 C17 C16 120.9(2) . . ? C16 C17 Cl20 120.5(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 C15 119.2(2) . . ? C17 C16 H16 120.4 . . ? 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 Cl20 C17 1.744(2) . ? O13 C11 1.294(2) . ? O13 H13 0.96(4) . ? N1 C2 1.344(2) . ? N1 C6 1.334(3) . ? O12 C11 1.207(2) . ? N7 H7 0.8600 . ? N7 C2 1.351(2) . ? N7 C8 1.448(2) . ? N3 C2 1.341(2) . ? N3 C4 1.333(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.501(3) . ? C10 C9 1.533(3) . ? C9 H9 0.9800 . ? C9 C14 1.519(3) . ? C9 C8 1.534(3) . ? C14 C19 1.380(3) . ? C14 C15 1.385(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C6 H6 0.9300 . ? C6 C5 1.368(3) . ? C19 H19 0.9300 . ? C19 C18 1.380(3) . ? C15 H15 0.9300 . ? C15 C16 1.387(3) . ? C5 H5 0.9300 . ? C5 C4 1.369(3) . ? C4 H4 0.9300 . ? C18 H18 0.9300 . ? C18 C17 1.367(4) . ? C17 C16 1.368(4) . ? C16 H16 0.9300 . ? 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 _geom_hbond_publ_flag N7 H7 O12 0.86 2.14 2.922(2) 150.3 2_655 yes O13 H13 N1 0.96(4) 1.68(4) 2.633(2) 170(3) 2_645 yes 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 Cl20 C17 C16 C15 179.90(17) . . . . ? N1 C6 C5 C4 0.6(4) . . . . ? C2 N1 C6 C5 0.2(3) . . . . ? C2 N7 C8 C9 -106.5(2) . . . . ? C2 N3 C4 C5 -0.2(3) . . . . ? C10 C9 C14 C19 121.3(2) . . . . ? C10 C9 C14 C15 -60.5(2) . . . . ? C10 C9 C8 N7 -70.8(2) . . . . ? C11 C10 C9 C14 -69.5(2) . . . . ? C11 C10 C9 C8 165.79(16) . . . . ? C9 C10 C11 O13 150.86(19) . . . . ? C9 C10 C11 O12 -31.6(3) . . . . ? C9 C14 C19 C18 178.4(2) . . . . ? C9 C14 C15 C16 -178.51(19) . . . . ? C14 C9 C8 N7 163.76(16) . . . . ? C14 C19 C18 C17 0.0(4) . . . . ? C14 C15 C16 C17 0.3(3) . . . . ? C8 N7 C2 N1 175.94(17) . . . . ? C8 N7 C2 N3 -5.1(3) . . . . ? C8 C9 C14 C19 -113.9(2) . . . . ? C8 C9 C14 C15 64.3(2) . . . . ? C6 N1 C2 N7 177.74(18) . . . . ? C6 N1 C2 N3 -1.1(3) . . . . ? C6 C5 C4 N3 -0.6(4) . . . . ? C19 C14 C15 C16 -0.3(3) . . . . ? C19 C18 C17 Cl20 179.97(19) . . . . ? C19 C18 C17 C16 0.0(4) . . . . ? C15 C14 C19 C18 0.2(3) . . . . ? C4 N3 C2 N1 1.1(3) . . . . ? C4 N3 C2 N7 -177.72(19) . . . . ? C18 C17 C16 C15 -0.2(4) . . . . ?