#------------------------------------------------------------------------------ #$Date: 2021-07-17 08:39:50 +0300 (Sat, 17 Jul 2021) $ #$Revision: 267615 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243240.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_7243240 loop_ _publ_author_name 'Ramle, Abdul Qaiyum' 'Fei, Chee Chin' 'Tiekink, Edward R. T.' 'Basirun, Wan Jefrey' _publ_section_title ; Indoleninyl-substituted pyrimido[1,2-b]indazoles via a facile condensation reaction ; _journal_issue 40 _journal_name_full 'RSC Advances' _journal_page_first 24647 _journal_page_last 24651 _journal_paper_doi 10.1039/D1RA04372B _journal_volume 11 _journal_year 2021 _chemical_formula_moiety 'C20 H16 N4' _chemical_formula_sum 'C20 H16 N4' _chemical_formula_weight 312.37 _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-10 deposited with the CCDC. 2021-07-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.4780(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.23710(10) _cell_length_b 6.86320(10) _cell_length_c 16.2164(3) _cell_measurement_reflns_used 6410 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 76.1380 _cell_measurement_theta_min 5.5670 _cell_volume 789.35(2) _computing_cell_refinement ; CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017) ; _computing_data_collection ; CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017) ; _computing_data_reduction ; CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017) ; _computing_molecular_graphics 'ORTEP-3 for Windows' _computing_publication_material SHELXL-2018/3 _computing_structure_refinement SHELXL-2018/3 _computing_structure_solution 'SHELXT 2014/5' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 294(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2558 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10920 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.300 _diffrn_reflns_theta_min 5.568 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.448 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.314 _exptl_crystal_description prism _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.221 _exptl_crystal_size_min 0.089 _refine_diff_density_max 0.838 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 143 _refine_ls_number_reflns 1774 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0687 _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^)+(0.1078P)^2^+0.4133P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1938 _refine_ls_wR_factor_ref 0.1978 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1622 _reflns_number_total 1774 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra04372b2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 7243240 _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_min 0.843 _shelx_estimated_absorpt_t_max 0.946 _shelx_res_file ; TITL 3a shelx.res created by SHELXL-2018/3 at 09:38:20 on 10-May-2021 CELL 1.54184 7.2371 6.8632 16.2164 90.000 101.478 90.000 ZERR 2 0.0001 0.0001 0.0003 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, - Z SFAC C H N UNIT 40 32 8 FMAP 2 PLAN 5 MERG 2 SIZE 0.089 0.221 0.280 ACTA BOND $H CONF L.S. 18 TEMP 21 WGHT 0.107800 0.413300 FVAR 1.08511 N1 3 0.634027 0.750000 0.151653 10.50000 0.03857 0.05521 = 0.04228 0.00000 0.00430 0.00000 N2 3 0.630908 0.750000 0.449515 10.50000 0.04529 0.06107 = 0.05062 0.00000 0.01676 0.00000 N3 3 0.920727 0.750000 0.399994 10.50000 0.03847 0.04413 = 0.04536 0.00000 0.01531 0.00000 N4 3 1.108751 0.750000 0.425128 10.50000 0.03683 0.06174 = 0.04372 0.00000 0.00930 0.00000 C1 1 0.539406 0.750000 0.211443 10.50000 0.03728 0.03651 = 0.04234 0.00000 0.00463 0.00000 C2 1 0.325264 0.750000 0.180867 10.50000 0.03562 0.04330 = 0.04908 0.00000 0.00578 0.00000 C3 1 0.319205 0.750000 0.087558 10.50000 0.04280 0.04379 = 0.04692 0.00000 -0.00139 0.00000 C4 1 0.169168 0.750000 0.019066 10.50000 0.04951 0.08177 = 0.06204 0.00000 -0.00937 0.00000 AFIX 43 H4 2 0.045112 0.750000 0.026627 10.50000 -1.20000 AFIX 0 C5 1 0.210361 0.750000 -0.061012 10.50000 0.07504 0.07980 = 0.04731 0.00000 -0.01480 0.00000 AFIX 43 H5 2 0.112094 0.750000 -0.107710 10.50000 -1.20000 AFIX 0 C6 1 0.393855 0.750000 -0.072695 10.50000 0.08827 0.06389 = 0.04350 0.00000 0.00121 0.00000 AFIX 43 H6 2 0.416611 0.750000 -0.127153 10.50000 -1.20000 AFIX 0 C7 1 0.543791 0.750000 -0.005881 10.50000 0.06325 0.06143 = 0.04639 0.00000 0.01169 0.00000 AFIX 43 H7 2 0.667576 0.750000 -0.013808 10.50000 -1.20000 AFIX 0 C8 1 0.502021 0.750000 0.074438 10.50000 0.04736 0.04181 = 0.04028 0.00000 0.00339 0.00000 C9 1 0.231856 0.565521 0.207441 11.00000 0.05382 0.05538 = 0.07318 -0.00073 0.01482 -0.01411 AFIX 137 H9A 2 0.293532 0.452371 0.190925 11.00000 -1.50000 H9B 2 0.101073 0.563565 0.180590 11.00000 -1.50000 H9C 2 0.242613 0.565384 0.267409 11.00000 -1.50000 AFIX 0 C10 1 0.637256 0.750000 0.300424 10.50000 0.04226 0.03974 = 0.04339 0.00000 0.00487 0.00000 C11 1 0.542686 0.750000 0.370056 10.50000 0.04584 0.05643 = 0.04720 0.00000 0.00910 0.00000 AFIX 43 H11 2 0.411560 0.750000 0.358604 10.50000 -1.20000 AFIX 0 C12 1 0.815761 0.750000 0.462976 10.50000 0.04358 0.03964 = 0.04881 0.00000 0.02317 0.00000 C13 1 0.828886 0.750000 0.317943 10.50000 0.04436 0.04810 = 0.04073 0.00000 0.00556 0.00000 AFIX 43 H13 2 0.896240 0.750000 0.274718 10.50000 -1.20000 AFIX 0 C14 1 0.954828 0.750000 0.539018 10.50000 0.05273 0.03723 = 0.04319 0.00000 0.00383 0.00000 C15 1 0.951021 0.750000 0.626398 10.50000 0.05496 0.05455 = 0.04992 0.00000 0.01907 0.00000 AFIX 43 H15 2 0.837709 0.750000 0.645196 10.50000 -1.20000 AFIX 0 C16 1 1.120178 0.750000 0.681559 10.50000 0.07366 0.05924 = 0.03684 0.00000 0.01086 0.00000 AFIX 43 H16 2 1.122740 0.750000 0.739125 10.50000 -1.20000 AFIX 0 C17 1 1.291292 0.750000 0.652283 10.50000 0.05446 0.05312 = 0.04442 0.00000 -0.00170 0.00000 AFIX 43 H17 2 1.404087 0.750000 0.691546 10.50000 -1.20000 AFIX 0 C18 1 1.298106 0.750000 0.569324 10.50000 0.05154 0.05200 = 0.04886 0.00000 0.01138 0.00000 AFIX 43 H18 2 1.412752 0.750000 0.551670 10.50000 -1.20000 AFIX 0 C19 1 1.126783 0.750000 0.511049 10.50000 0.05333 0.03835 = 0.03999 0.00000 0.01033 0.00000 HKLF 4 REM 3a REM wR2 = 0.1978, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0687 for 1622 Fo > 4sig(Fo) and 0.0717 for all 1774 data REM 143 parameters refined using 0 restraints END WGHT 0.1074 0.4078 REM Highest difference peak 0.838, deepest hole -0.284, 1-sigma level 0.055 Q1 1 1.0185 0.7500 0.3557 10.50000 0.05 0.84 Q2 1 0.7371 0.7500 0.5151 10.50000 0.05 0.80 Q3 1 0.6450 0.7500 0.3585 10.50000 0.05 0.50 Q4 1 0.7470 0.7500 0.4236 10.50000 0.05 0.32 Q5 1 0.9237 0.7500 0.5785 10.50000 0.05 0.30 ; _shelx_res_checksum 29695 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-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 N1 N 0.6340(3) 0.750000 0.15165(15) 0.0459(6) Uani 1 2 d S T P . . N2 N 0.6309(3) 0.750000 0.44951(16) 0.0513(6) Uani 1 2 d S T P . . N3 N 0.9207(3) 0.750000 0.39999(14) 0.0417(5) Uani 1 2 d S T P . . N4 N 1.1088(3) 0.750000 0.42513(15) 0.0473(6) Uani 1 2 d S T P . . C1 C 0.5394(4) 0.750000 0.21144(17) 0.0392(6) Uani 1 2 d S T P . . C2 C 0.3253(4) 0.750000 0.18087(18) 0.0430(6) Uani 1 2 d S T P . . C3 C 0.3192(4) 0.750000 0.08756(18) 0.0459(7) Uani 1 2 d S T P . . C4 C 0.1692(5) 0.750000 0.0191(2) 0.0673(10) Uani 1 2 d S T P . . H4 H 0.045112 0.750000 0.026627 0.081 Uiso 1 2 calc R U P . . C5 C 0.2104(6) 0.750000 -0.0610(2) 0.0711(10) Uani 1 2 d S T P . . H5 H 0.112094 0.750000 -0.107710 0.085 Uiso 1 2 calc R U P . . C6 C 0.3939(6) 0.750000 -0.0727(2) 0.0669(10) Uani 1 2 d S T P . . H6 H 0.416611 0.750000 -0.127153 0.080 Uiso 1 2 calc R U P . . C7 C 0.5438(5) 0.750000 -0.0059(2) 0.0569(8) Uani 1 2 d S T P . . H7 H 0.667576 0.750000 -0.013808 0.068 Uiso 1 2 calc R U P . . C8 C 0.5020(4) 0.750000 0.07444(17) 0.0439(6) Uani 1 2 d S T P . . C9 C 0.2319(3) 0.5655(4) 0.20744(16) 0.0605(6) Uani 1 1 d . . . . . H9A H 0.293532 0.452371 0.190925 0.091 Uiso 1 1 calc R U . . . H9B H 0.101073 0.563565 0.180590 0.091 Uiso 1 1 calc R U . . . H9C H 0.242613 0.565384 0.267409 0.091 Uiso 1 1 calc R U . . . C10 C 0.6373(4) 0.750000 0.30042(17) 0.0423(6) Uani 1 2 d S T P . . C11 C 0.5427(4) 0.750000 0.37006(18) 0.0498(7) Uani 1 2 d S T P . . H11 H 0.411560 0.750000 0.358604 0.060 Uiso 1 2 calc R U P . . C12 C 0.8158(4) 0.750000 0.46298(18) 0.0421(6) Uani 1 2 d S T P . . C13 C 0.8289(4) 0.750000 0.31794(17) 0.0448(6) Uani 1 2 d S T P . . H13 H 0.896240 0.750000 0.274718 0.054 Uiso 1 2 calc R U P . . C14 C 0.9548(4) 0.750000 0.53902(18) 0.0452(7) Uani 1 2 d S T P . . C15 C 0.9510(5) 0.750000 0.62640(19) 0.0520(7) Uani 1 2 d S T P . . H15 H 0.837709 0.750000 0.645196 0.062 Uiso 1 2 calc R U P . . C16 C 1.1202(5) 0.750000 0.68156(19) 0.0566(8) Uani 1 2 d S T P . . H16 H 1.122740 0.750000 0.739125 0.068 Uiso 1 2 calc R U P . . C17 C 1.2913(5) 0.750000 0.65228(19) 0.0523(7) Uani 1 2 d S T P . . H17 H 1.404087 0.750000 0.691546 0.063 Uiso 1 2 calc R U P . . C18 C 1.2981(4) 0.750000 0.56932(19) 0.0506(7) Uani 1 2 d S T P . . H18 H 1.412752 0.750000 0.551670 0.061 Uiso 1 2 calc R U P . . C19 C 1.1268(4) 0.750000 0.51105(17) 0.0437(6) Uani 1 2 d S T P . . 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 N1 0.0386(12) 0.0552(14) 0.0423(12) 0.000 0.0043(9) 0.000 N2 0.0453(13) 0.0611(15) 0.0506(14) 0.000 0.0168(10) 0.000 N3 0.0385(11) 0.0441(12) 0.0454(12) 0.000 0.0153(9) 0.000 N4 0.0368(12) 0.0617(15) 0.0437(13) 0.000 0.0093(9) 0.000 C1 0.0373(13) 0.0365(12) 0.0423(14) 0.000 0.0046(10) 0.000 C2 0.0356(13) 0.0433(14) 0.0491(15) 0.000 0.0058(11) 0.000 C3 0.0428(14) 0.0438(14) 0.0469(15) 0.000 -0.0014(12) 0.000 C4 0.0495(17) 0.082(2) 0.062(2) 0.000 -0.0094(15) 0.000 C5 0.075(2) 0.080(2) 0.0473(18) 0.000 -0.0148(16) 0.000 C6 0.088(3) 0.064(2) 0.0435(17) 0.000 0.0012(16) 0.000 C7 0.063(2) 0.0614(19) 0.0464(16) 0.000 0.0117(14) 0.000 C8 0.0474(15) 0.0418(14) 0.0403(14) 0.000 0.0034(11) 0.000 C9 0.0538(12) 0.0554(13) 0.0732(15) -0.0007(11) 0.0148(10) -0.0141(10) C10 0.0423(14) 0.0397(13) 0.0434(14) 0.000 0.0049(11) 0.000 C11 0.0458(15) 0.0564(17) 0.0472(15) 0.000 0.0091(12) 0.000 C12 0.0436(14) 0.0396(13) 0.0488(15) 0.000 0.0232(11) 0.000 C13 0.0444(15) 0.0481(15) 0.0407(14) 0.000 0.0056(11) 0.000 C14 0.0527(16) 0.0372(13) 0.0432(15) 0.000 0.0038(11) 0.000 C15 0.0550(17) 0.0545(16) 0.0499(16) 0.000 0.0191(13) 0.000 C16 0.074(2) 0.0592(18) 0.0368(14) 0.000 0.0109(14) 0.000 C17 0.0545(17) 0.0531(16) 0.0444(15) 0.000 -0.0017(12) 0.000 C18 0.0515(16) 0.0520(16) 0.0489(16) 0.000 0.0114(12) 0.000 C19 0.0533(16) 0.0384(13) 0.0400(14) 0.000 0.0103(12) 0.000 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' 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 C1 N1 C8 107.4(2) . . ? C12 N2 C11 116.2(2) . . ? N4 N3 C13 124.4(2) . . ? N4 N3 C12 116.6(2) . . ? C13 N3 C12 119.1(2) . . ? N3 N4 C19 101.2(2) . . ? N1 C1 C10 120.7(2) . . ? N1 C1 C2 114.2(2) . . ? C10 C1 C2 125.1(2) . . ? C3 C2 C1 98.7(2) . . ? C3 C2 C9 110.82(16) . . ? C1 C2 C9 112.51(15) . . ? C3 C2 C9 110.82(16) . 4_575 ? C1 C2 C9 112.51(15) . 4_575 ? C9 C2 C9 110.9(3) . 4_575 ? C8 C3 C4 119.8(3) . . ? C8 C3 C2 108.5(2) . . ? C4 C3 C2 131.7(3) . . ? C5 C4 C3 117.9(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C6 C5 C4 121.4(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 121.6(3) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C6 C7 C8 116.9(3) . . ? C6 C7 H7 121.5 . . ? C8 C7 H7 121.5 . . ? C3 C8 C7 122.4(3) . . ? C3 C8 N1 111.2(2) . . ? C7 C8 N1 126.3(3) . . ? C2 C9 H9A 109.5 . . ? C2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C13 C10 C11 117.6(3) . . ? C13 C10 C1 118.4(3) . . ? C11 C10 C1 124.0(3) . . ? N2 C11 C10 123.8(3) . . ? N2 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? N2 C12 N3 124.5(3) . . ? N2 C12 C14 131.6(2) . . ? N3 C12 C14 103.9(2) . . ? C10 C13 N3 118.9(3) . . ? C10 C13 H13 120.6 . . ? N3 C13 H13 120.6 . . ? C19 C14 C15 121.0(3) . . ? C19 C14 C12 103.8(2) . . ? C15 C14 C12 135.2(3) . . ? C16 C15 C14 117.4(3) . . ? C16 C15 H15 121.3 . . ? C14 C15 H15 121.3 . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 122.8(3) . . ? C18 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? C17 C18 C19 117.8(3) . . ? C17 C18 H18 121.1 . . ? C19 C18 H18 121.1 . . ? N4 C19 C18 125.2(3) . . ? N4 C19 C14 114.6(3) . . ? C18 C19 C14 120.2(3) . . ? 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 N1 C1 1.294(4) . ? N1 C8 1.416(3) . ? N2 C12 1.312(4) . ? N2 C11 1.319(4) . ? N3 N4 1.341(3) . ? N3 C13 1.364(4) . ? N3 C12 1.389(3) . ? N4 C19 1.373(3) . ? C1 C10 1.475(4) . ? C1 C2 1.530(3) . ? C2 C3 1.505(4) . ? C2 C9 1.537(3) . ? C2 C9 1.537(3) 4_575 ? C3 C8 1.381(4) . ? C3 C4 1.390(4) . ? C4 C5 1.389(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(6) . ? C5 H5 0.9300 . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 C8 1.394(4) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C13 1.359(4) . ? C10 C11 1.432(4) . ? C11 H11 0.9300 . ? C12 C14 1.428(4) . ? C13 H13 0.9300 . ? C14 C19 1.407(4) . ? C14 C15 1.423(4) . ? C15 C16 1.365(5) . ? C15 H15 0.9300 . ? C16 C17 1.412(5) . ? C16 H16 0.9300 . ? C17 C18 1.356(4) . ? C17 H17 0.9300 . ? C18 C19 1.401(4) . ? C18 H18 0.9300 . ? 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 C13 N3 N4 C19 180.000(1) . . . . ? C12 N3 N4 C19 0.000(1) . . . . ? C8 N1 C1 C10 180.000(0) . . . . ? C8 N1 C1 C2 0.000(0) . . . . ? N1 C1 C2 C3 0.000(0) . . . . ? C10 C1 C2 C3 180.000(0) . . . . ? N1 C1 C2 C9 116.90(18) . . . . ? C10 C1 C2 C9 -63.10(18) . . . . ? N1 C1 C2 C9 -116.90(18) . . . 4_575 ? C10 C1 C2 C9 63.10(18) . . . 4_575 ? C1 C2 C3 C8 0.000(0) . . . . ? C9 C2 C3 C8 -118.18(16) . . . . ? C9 C2 C3 C8 118.18(16) 4_575 . . . ? C1 C2 C3 C4 180.000(0) . . . . ? C9 C2 C3 C4 61.82(16) . . . . ? C9 C2 C3 C4 -61.82(16) 4_575 . . . ? C8 C3 C4 C5 0.000(0) . . . . ? C2 C3 C4 C5 180.000(0) . . . . ? C3 C4 C5 C6 0.000(0) . . . . ? C4 C5 C6 C7 0.000(0) . . . . ? C5 C6 C7 C8 0.000(0) . . . . ? C4 C3 C8 C7 0.000(0) . . . . ? C2 C3 C8 C7 180.000(0) . . . . ? C4 C3 C8 N1 180.000(0) . . . . ? C2 C3 C8 N1 0.000(0) . . . . ? C6 C7 C8 C3 0.000(0) . . . . ? C6 C7 C8 N1 180.000(0) . . . . ? C1 N1 C8 C3 0.000(0) . . . . ? C1 N1 C8 C7 180.000(0) . . . . ? N1 C1 C10 C13 0.000(1) . . . . ? C2 C1 C10 C13 180.000(0) . . . . ? N1 C1 C10 C11 180.000(1) . . . . ? C2 C1 C10 C11 0.000(1) . . . . ? C12 N2 C11 C10 0.000(1) . . . . ? C13 C10 C11 N2 0.000(1) . . . . ? C1 C10 C11 N2 180.000(1) . . . . ? C11 N2 C12 N3 0.000(1) . . . . ? C11 N2 C12 C14 180.000(1) . . . . ? N4 N3 C12 N2 180.000(1) . . . . ? C13 N3 C12 N2 0.000(1) . . . . ? N4 N3 C12 C14 0.000(1) . . . . ? C13 N3 C12 C14 180.000(1) . . . . ? C11 C10 C13 N3 0.000(1) . . . . ? C1 C10 C13 N3 180.000(1) . . . . ? N4 N3 C13 C10 180.000(1) . . . . ? C12 N3 C13 C10 0.000(1) . . . . ? N2 C12 C14 C19 180.000(1) . . . . ? N3 C12 C14 C19 0.000(1) . . . . ? N2 C12 C14 C15 0.000(2) . . . . ? N3 C12 C14 C15 180.000(1) . . . . ? C19 C14 C15 C16 0.000(2) . . . . ? C12 C14 C15 C16 180.000(2) . . . . ? C14 C15 C16 C17 0.000(2) . . . . ? C15 C16 C17 C18 0.000(2) . . . . ? C16 C17 C18 C19 0.000(2) . . . . ? N3 N4 C19 C18 180.000(1) . . . . ? N3 N4 C19 C14 0.000(1) . . . . ? C17 C18 C19 N4 180.000(1) . . . . ? C17 C18 C19 C14 0.000(2) . . . . ? C15 C14 C19 N4 180.000(1) . . . . ? C12 C14 C19 N4 0.000(1) . . . . ? C15 C14 C19 C18 0.000(2) . . . . ? C12 C14 C19 C18 180.000(1) . . . . ?