#------------------------------------------------------------------------------ #$Date: 2020-06-03 05:53:35 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252561 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240593.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_7240593 loop_ _publ_author_name 'Poirier, Marion' 'Pujol-Gim\'enez, Jonai' 'Manatschal, Cristina' 'B\"uhlmann, Sven' 'Embaby, Ahmed' 'Javor, Sacha' 'Hediger, Matthias A.' 'Reymond, Jean-Louis' _publ_section_title ; Pyrazolyl-pyrimidones inhibit the function of human solute carrier protein SLC11A2 (hDMT1) by metal chelation ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D0MD00085J _journal_year 2020 _chemical_formula_sum 'C14 H18 N4 O' _chemical_formula_weight 258.32 _chemical_name_systematic 2-(3-ethyl-4,5,6,7-tetrahydro-2H-indazol-2-yl)-6-methylpyrimidin-4(3H)-one _space_group_IT_number 60 _space_group_name_Hall '-P 2n 2ab' _space_group_name_H-M_alt 'P b c n' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 60 _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_sites_solution_hydrogens mixed _audit_creation_date 2016-12-12T15:01:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2020-01-10 deposited with the CCDC. 2020-05-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.8002(2) _cell_length_b 9.62410(10) _cell_length_c 14.3730(2) _cell_measurement_reflns_used 6648 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.047 _cell_measurement_theta_min 2.152 _cell_volume 2600.58(5) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET) (compiled Dec 9 2014,15:38:47) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET) (compiled Dec 9 2014,15:38:47) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET) (compiled Dec 9 2014,15:38:47) ; _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 173(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0965 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.921 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0006431 _diffrn_orient_matrix_UB_12 -0.067915 _diffrn_orient_matrix_UB_13 -0.0191959 _diffrn_orient_matrix_UB_21 0.0377157 _diffrn_orient_matrix_UB_22 0.001185 _diffrn_orient_matrix_UB_23 0.0002959 _diffrn_orient_matrix_UB_31 0.0000361 _diffrn_orient_matrix_UB_32 -0.0286619 _diffrn_orient_matrix_UB_33 0.0454544 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_Laue_measured_fraction_full 1 _diffrn_reflns_Laue_measured_fraction_max 0.921 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 14668 _diffrn_reflns_point_group_measured_fraction_full 1 _diffrn_reflns_point_group_measured_fraction_max 0.921 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 28.142 _diffrn_reflns_theta_min 2.167 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET) (compiled Dec 9 2014,15:38:47) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.32 _exptl_crystal_description prism _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.3237 _exptl_crystal_size_mid 0.2243 _exptl_crystal_size_min 0.1952 _refine_diff_density_max 0.231 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.0037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 179 _refine_ls_number_reflns 2933 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.044 _refine_ls_R_factor_gt 0.0355 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.7943P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.0938 _reflns_Friedel_coverage 0 _reflns_number_gt 2475 _reflns_number_total 2933 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0md00085j3.cif _cod_data_source_block 16jlr003 _cod_database_code 7240593 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL shelxt_a.res in Pbcn CELL 0.71073 18.8002 9.6241 14.3730 90.000 90.000 90.000 ZERR 8.00 0.0002 0.0001 0.0002 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, 1/2 - Y, 1/2 + Z SYMM - X, Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O UNIT 112 144 32 8 MERG 2 FMAP 2 PLAN 20 ACTA 50.00 BOND $H LIST 6 L.S. 10 TEMP -100.00 WGHT 0.038800 0.794300 EXTI 0.003709 FVAR 3.96853 C1 1 0.328952 0.406081 0.556951 11.00000 0.01731 0.03530 = 0.02558 -0.00398 0.00131 -0.00097 C2 1 0.331734 0.258107 0.565329 11.00000 0.01970 0.03330 = 0.02418 -0.00115 0.00130 -0.00594 AFIX 43 H2 2 0.290268 0.204521 0.553520 11.00000 -1.20000 AFIX 0 C3 1 0.393201 0.193421 0.590047 11.00000 0.02517 0.03054 = 0.02380 0.00375 0.00197 -0.00525 C4 1 0.398385 0.039539 0.600581 11.00000 0.03460 0.03131 = 0.05076 0.00824 -0.00550 -0.00694 AFIX 137 H4A 2 0.352157 -0.002713 0.586713 11.00000 -1.50000 H4B 2 0.412185 0.016889 0.664559 11.00000 -1.50000 H4C 2 0.434217 0.003358 0.557392 11.00000 -1.50000 AFIX 0 C5 1 0.452572 0.397434 0.602081 11.00000 0.01702 0.03011 = 0.01857 0.00118 0.00099 -0.00135 C6 1 0.578460 0.441675 0.657062 11.00000 0.01706 0.03425 = 0.02053 0.00236 -0.00050 0.00025 C7 1 0.612712 0.564172 0.673837 11.00000 0.01815 0.03492 = 0.02066 -0.00181 0.00160 -0.00147 C8 1 0.565025 0.671513 0.648739 11.00000 0.01806 0.03171 = 0.02336 -0.00372 0.00330 -0.00184 C9 1 0.580260 0.822844 0.659618 11.00000 0.02269 0.03274 = 0.03767 -0.00810 0.00234 -0.00266 AFIX 23 H9A 2 0.551118 0.861065 0.710963 11.00000 -1.20000 H9B 2 0.567217 0.872396 0.601717 11.00000 -1.20000 AFIX 0 C10 1 0.659440 0.846453 0.680680 11.00000 0.02475 0.03827 = 0.03434 -0.00492 0.00218 -0.00870 AFIX 23 H10A 2 0.687071 0.839029 0.622256 11.00000 -1.20000 H10B 2 0.666099 0.941406 0.705701 11.00000 -1.20000 AFIX 0 C11 1 0.687532 0.740992 0.750772 11.00000 0.02465 0.04842 = 0.03034 -0.00335 -0.00313 -0.01138 AFIX 23 H11A 2 0.658210 0.744683 0.807931 11.00000 -1.20000 H11B 2 0.737001 0.765351 0.767844 11.00000 -1.20000 AFIX 0 C12 1 0.685851 0.593777 0.711088 11.00000 0.01810 0.04390 = 0.02998 0.00068 -0.00271 -0.00361 AFIX 23 H12A 2 0.721371 0.584925 0.660585 11.00000 -1.20000 H12B 2 0.697914 0.525935 0.760401 11.00000 -1.20000 AFIX 0 C13 1 0.605401 0.296292 0.666790 11.00000 0.02177 0.03390 = 0.03486 0.00901 -0.00613 0.00046 AFIX 23 H13A 2 0.567168 0.237252 0.692876 11.00000 -1.20000 H13B 2 0.645644 0.295483 0.711211 11.00000 -1.20000 AFIX 0 C14 1 0.629941 0.234848 0.574583 11.00000 0.03526 0.03133 = 0.04940 0.00088 0.00000 0.00976 AFIX 137 H14A 2 0.589444 0.228769 0.531844 11.00000 -1.50000 H14B 2 0.649442 0.141746 0.585164 11.00000 -1.50000 H14C 2 0.666728 0.294486 0.547400 11.00000 -1.50000 AFIX 0 N1 3 0.393962 0.470240 0.577530 11.00000 0.01757 0.02614 = 0.02951 -0.00147 -0.00047 -0.00049 N2 3 0.455800 0.263765 0.608619 11.00000 0.02035 0.02980 = 0.02802 0.00490 -0.00176 -0.00233 N3 3 0.511925 0.479451 0.622450 11.00000 0.01706 0.02710 = 0.02543 0.00109 -0.00124 -0.00067 N4 3 0.503831 0.621688 0.617669 11.00000 0.01950 0.02627 = 0.02846 -0.00213 0.00021 -0.00064 O1 4 0.277445 0.478198 0.536036 11.00000 0.01845 0.03855 = 0.05489 -0.00476 -0.00494 0.00413 H1 2 0.397467 0.561619 0.575374 11.00000 0.03806 HKLF 4 REM shelxt_a.res in Pbcn REM R1 = 0.0355 for 2475 Fo > 4sig(Fo) and 0.0440 for all 2933 data REM 179 parameters refined using 0 restraints END WGHT 0.0388 0.7928 REM Highest difference peak 0.231, deepest hole -0.182, 1-sigma level 0.035 Q1 1 0.5897 0.3675 0.6597 11.00000 0.05 0.23 Q2 1 0.5484 0.4466 0.6392 11.00000 0.05 0.23 Q3 1 0.5873 0.6195 0.6729 11.00000 0.05 0.23 Q4 1 0.6091 0.4990 0.6446 11.00000 0.05 0.23 Q5 1 0.5982 0.6255 0.6480 11.00000 0.05 0.20 Q6 1 0.6455 0.5727 0.6939 11.00000 0.05 0.19 Q7 1 0.4798 0.4358 0.6186 11.00000 0.05 0.19 Q8 1 0.4224 0.2306 0.5983 11.00000 0.05 0.19 Q9 1 0.3695 0.2269 0.5547 11.00000 0.05 0.19 Q10 1 0.6001 0.5013 0.6776 11.00000 0.05 0.19 Q11 1 0.3349 0.3248 0.5470 11.00000 0.05 0.17 Q12 1 0.3902 0.1210 0.6015 11.00000 0.05 0.17 Q13 1 0.5796 0.7383 0.6386 11.00000 0.05 0.17 Q14 1 0.3602 0.2340 0.6023 11.00000 0.05 0.17 Q15 1 0.6190 0.8292 0.6644 11.00000 0.05 0.16 Q16 1 0.4913 0.2167 0.6198 11.00000 0.05 0.15 Q17 1 0.4209 0.4323 0.5866 11.00000 0.05 0.14 Q18 1 0.4419 0.3364 0.6353 11.00000 0.05 0.14 Q19 1 0.4633 0.6608 0.6231 11.00000 0.05 0.14 Q20 1 0.5440 0.6572 0.6238 11.00000 0.05 0.14 ; _shelx_res_checksum 70304 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, 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 C1 C 0.32895(5) 0.40608(13) 0.55695(8) 0.0261(3) Uani 1 1 d . . . . . C2 C 0.33173(6) 0.25811(13) 0.56533(8) 0.0257(3) Uani 1 1 d . . . . . H2 H 0.2903 0.2045 0.5535 0.031 Uiso 1 1 calc R U . . . C3 C 0.39320(6) 0.19342(13) 0.59005(8) 0.0265(3) Uani 1 1 d . . . . . C4 C 0.39838(7) 0.03954(14) 0.60058(11) 0.0389(3) Uani 1 1 d . . . . . H4A H 0.3522 -0.0027 0.5867 0.058 Uiso 1 1 calc R U . . . H4B H 0.4122 0.0169 0.6646 0.058 Uiso 1 1 calc R U . . . H4C H 0.4342 0.0034 0.5574 0.058 Uiso 1 1 calc R U . . . C5 C 0.45257(5) 0.39743(12) 0.60208(7) 0.0219(2) Uani 1 1 d . . . . . C6 C 0.57846(5) 0.44168(12) 0.65706(8) 0.0239(3) Uani 1 1 d . . . . . C7 C 0.61271(5) 0.56417(13) 0.67384(8) 0.0246(3) Uani 1 1 d . . . . . C8 C 0.56502(6) 0.67151(12) 0.64874(8) 0.0244(3) Uani 1 1 d . . . . . C9 C 0.58026(6) 0.82284(13) 0.65962(9) 0.0310(3) Uani 1 1 d . . . . . H9A H 0.5511 0.8611 0.711 0.037 Uiso 1 1 calc R U . . . H9B H 0.5672 0.8724 0.6017 0.037 Uiso 1 1 calc R U . . . C10 C 0.65944(6) 0.84645(14) 0.68068(9) 0.0325(3) Uani 1 1 d . . . . . H10A H 0.6871 0.839 0.6223 0.039 Uiso 1 1 calc R U . . . H10B H 0.6661 0.9414 0.7057 0.039 Uiso 1 1 calc R U . . . C11 C 0.68753(6) 0.74099(14) 0.75077(9) 0.0345(3) Uani 1 1 d . . . . . H11A H 0.6582 0.7447 0.8079 0.041 Uiso 1 1 calc R U . . . H11B H 0.737 0.7654 0.7678 0.041 Uiso 1 1 calc R U . . . C12 C 0.68585(6) 0.59378(14) 0.71109(9) 0.0307(3) Uani 1 1 d . . . . . H12A H 0.7214 0.5849 0.6606 0.037 Uiso 1 1 calc R U . . . H12B H 0.6979 0.5259 0.7604 0.037 Uiso 1 1 calc R U . . . C13 C 0.60540(6) 0.29629(13) 0.66679(9) 0.0302(3) Uani 1 1 d . . . . . H13A H 0.5672 0.2373 0.6929 0.036 Uiso 1 1 calc R U . . . H13B H 0.6456 0.2955 0.7112 0.036 Uiso 1 1 calc R U . . . C14 C 0.62994(7) 0.23485(14) 0.57458(10) 0.0387(3) Uani 1 1 d . . . . . H14A H 0.5894 0.2288 0.5318 0.058 Uiso 1 1 calc R U . . . H14B H 0.6494 0.1417 0.5852 0.058 Uiso 1 1 calc R U . . . H14C H 0.6667 0.2945 0.5474 0.058 Uiso 1 1 calc R U . . . N1 N 0.39396(5) 0.47024(11) 0.57753(7) 0.0244(2) Uani 1 1 d . . . . . N2 N 0.45580(5) 0.26377(10) 0.60862(7) 0.0261(2) Uani 1 1 d . . . . . N3 N 0.51192(4) 0.47945(10) 0.62245(6) 0.0232(2) Uani 1 1 d . . . . . N4 N 0.50383(5) 0.62169(10) 0.61767(7) 0.0247(2) Uani 1 1 d . . . . . O1 O 0.27745(4) 0.47820(10) 0.53604(7) 0.0373(2) Uani 1 1 d . . . . . H1 H 0.3975(7) 0.5616(16) 0.5754(10) 0.038(4) 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 0.0173(5) 0.0353(7) 0.0256(6) -0.0040(5) 0.0013(4) -0.0010(4) C2 0.0197(5) 0.0333(7) 0.0242(6) -0.0012(5) 0.0013(4) -0.0059(4) C3 0.0252(5) 0.0305(6) 0.0238(6) 0.0038(5) 0.0020(4) -0.0052(5) C4 0.0346(6) 0.0313(7) 0.0508(9) 0.0082(6) -0.0055(6) -0.0069(5) C5 0.0170(5) 0.0301(6) 0.0186(5) 0.0012(4) 0.0010(4) -0.0013(4) C6 0.0171(5) 0.0343(6) 0.0205(6) 0.0024(5) -0.0005(4) 0.0002(4) C7 0.0181(5) 0.0349(7) 0.0207(6) -0.0018(5) 0.0016(4) -0.0015(4) C8 0.0181(5) 0.0317(6) 0.0234(6) -0.0037(5) 0.0033(4) -0.0018(4) C9 0.0227(5) 0.0327(7) 0.0377(7) -0.0081(5) 0.0023(5) -0.0027(5) C10 0.0248(6) 0.0383(7) 0.0343(7) -0.0049(5) 0.0022(5) -0.0087(5) C11 0.0247(5) 0.0484(8) 0.0303(7) -0.0034(6) -0.0031(5) -0.0114(5) C12 0.0181(5) 0.0439(7) 0.0300(7) 0.0007(5) -0.0027(4) -0.0036(5) C13 0.0218(5) 0.0339(7) 0.0349(7) 0.0090(5) -0.0061(5) 0.0005(5) C14 0.0353(6) 0.0313(7) 0.0494(8) 0.0009(6) 0.0000(6) 0.0098(5) N1 0.0176(4) 0.0261(5) 0.0295(5) -0.0015(4) -0.0005(4) -0.0005(4) N2 0.0203(4) 0.0298(5) 0.0280(5) 0.0049(4) -0.0018(4) -0.0023(4) N3 0.0171(4) 0.0271(5) 0.0254(5) 0.0011(4) -0.0012(4) -0.0007(4) N4 0.0195(4) 0.0263(5) 0.0285(5) -0.0021(4) 0.0002(4) -0.0006(4) O1 0.0184(4) 0.0386(5) 0.0549(6) -0.0048(4) -0.0049(4) 0.0041(3) 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 1 0 0 0.0976 -1 0 0 0.0976 0 0 1 0.1121 0 0 -1 0.1121 0 1 0 0.1658 0 -1 0 0.1578 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 O1 C1 N1 119.36(11) . . ? O1 C1 C2 127.73(10) . . ? N1 C1 C2 112.91(10) . . ? C3 C2 C1 120.59(10) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 N2 123.31(11) . . ? C2 C3 C4 122.44(11) . . ? N2 C3 C4 114.24(10) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 N1 124.98(10) . . ? N2 C5 N3 120.65(10) . . ? N1 C5 N3 114.36(10) . . ? C7 C6 N3 105.13(10) . . ? C7 C6 C13 129.22(10) . . ? N3 C6 C13 125.55(10) . . ? C6 C7 C8 106.66(9) . . ? C6 C7 C12 131.18(11) . . ? C8 C7 C12 122.16(11) . . ? N4 C8 C7 111.85(10) . . ? N4 C8 C9 123.75(11) . . ? C7 C8 C9 124.35(10) . . ? C8 C9 C10 110.55(10) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C11 C10 C9 111.56(10) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108 . . ? C10 C11 C12 111.32(11) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? C7 C12 C11 109.13(10) . . ? C7 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? C7 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C6 C13 C14 112.63(10) . . ? C6 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C6 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 N1 C1 122.51(10) . . ? C5 N1 H1 117.7(9) . . ? C1 N1 H1 119.8(9) . . ? C5 N2 C3 115.69(10) . . ? N4 N3 C6 112.06(9) . . ? N4 N3 C5 117.52(9) . . ? C6 N3 C5 130.06(10) . . ? C8 N4 N3 104.29(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 C1 O1 1.2287(14) . ? C1 N1 1.4009(14) . ? C1 C2 1.4302(17) . ? C2 C3 1.3599(16) . ? C2 H2 0.95 . ? C3 N2 1.3837(14) . ? C3 C4 1.4919(17) . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 N2 1.2913(15) . ? C5 N1 1.3526(14) . ? C5 N3 1.3978(13) . ? C6 C7 1.3648(16) . ? C6 N3 1.3944(13) . ? C6 C13 1.4946(17) . ? C7 C8 1.4146(16) . ? C7 C12 1.5029(14) . ? C8 N4 1.3240(14) . ? C8 C9 1.4925(17) . ? C9 C10 1.5360(15) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.5245(19) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.5276(18) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.5228(19) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? N1 H1 0.882(15) . ? N3 N4 1.3790(14) . ?