#------------------------------------------------------------------------------ #$Date: 2023-01-25 12:26:57 +0200 (Wed, 25 Jan 2023) $ #$Revision: 280604 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106597.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_8106597 loop_ _publ_author_name 'Yuan, Lin' 'Li, Zhong-Yan' 'Yuan, Xian-You' 'Zhang, Min' 'Liu, Fang' _publ_section_title ; Crystal structure of 1,3-dimethyl-2-phenyl-1H-perimidin-3-ium iodide, C19H17IN2 ; _journal_issue 4 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 541 _journal_page_last 543 _journal_paper_doi 10.1515/ncrs-2016-0302 _journal_volume 232 _journal_year 2017 _chemical_formula_moiety 'C19 H17 N2, I' _chemical_formula_sum 'C19 H17 I N2' _chemical_formula_weight 400.25 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 111.168(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 18.701(4) _cell_length_b 7.9230(16) _cell_length_c 24.069(6) _cell_measurement_reflns_used 9875 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 2.34 _cell_volume 3325.6(13) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_unetI/netI 0.0093 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 14906 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 1.81 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.924 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5777 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0791 before and 0.0291 after correction. The Ratio of minimum to maximum transmission is 0.7748. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1584 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.223 _refine_diff_density_min -0.611 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 203 _refine_ls_number_reflns 2887 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0213 _refine_ls_R_factor_gt 0.0201 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0162P)^2^+4.1997P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.0462 _reflns_number_gt 2763 _reflns_number_total 2887 _reflns_threshold_expression >2sigma(I) _cod_data_source_file suppl_ncrs-2016-0302_suppl.cif _cod_data_source_block 1 _cod_database_code 8106597 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C9(H9), C16(H16), C3(H3), C17(H17), C15(H15), C8(H8), C19(H19), C18(H18), C5(H5), C7(H7), C4(H4) 2.b Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 '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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_site_symmetry_order _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy N1 N 0.02337(10) 0.0880(2) 0.10919(7) 0.0404(4) Uani 1 d . . 1 . . . N2 N 0.00485(9) 0.3438(2) 0.14921(7) 0.0412(4) Uani 1 d . . 1 . . . C2 C -0.05664(12) 0.0579(3) 0.08300(9) 0.0415(4) Uani 1 d . . 1 . . . C14 C 0.13526(12) 0.2481(3) 0.16972(10) 0.0430(5) Uani 1 d . . 1 . . . C11 C 0.05110(11) 0.2267(2) 0.14101(9) 0.0392(4) Uani 1 d . . 1 . . . C1 C -0.10546(11) 0.1761(2) 0.09493(8) 0.0396(4) Uani 1 d . . 1 . . . C6 C -0.18568(12) 0.1482(3) 0.07256(9) 0.0483(5) Uani 1 d . . 1 . . . C10 C -0.07554(11) 0.3222(3) 0.12880(9) 0.0410(4) Uani 1 d . . 1 . . . C9 C -0.12331(14) 0.4357(3) 0.14080(11) 0.0569(6) Uani 1 d . . 1 . . . H9 H -0.1035 0.5329 0.1626 0.068 Uiso 1 calc . . 1 R . . C16 C 0.25785(14) 0.3241(3) 0.16719(13) 0.0608(6) Uani 1 d . . 1 . . . H16 H 0.2876 0.3660 0.1466 0.073 Uiso 1 calc . . 1 R . . C3 C -0.08599(14) -0.0823(3) 0.04876(11) 0.0569(6) Uani 1 d . . 1 . . . H3 H -0.0537 -0.1605 0.0410 0.068 Uiso 1 calc . . 1 R . . C17 C 0.29231(13) 0.2778(3) 0.22568(12) 0.0583(6) Uani 1 d . . 1 . . . H17 H 0.3452 0.2870 0.2445 0.070 Uiso 1 calc . . 1 R . . C12 C 0.07474(14) -0.0462(3) 0.10397(12) 0.0593(6) Uani 1 d . . 1 . . . H12A H 0.0642 -0.1485 0.1210 0.089 Uiso 1 calc . . 1 GR . . H12B H 0.1270 -0.0134 0.1248 0.089 Uiso 1 calc . . 1 GR . . H12C H 0.0666 -0.0646 0.0627 0.089 Uiso 1 calc . . 1 GR . . C15 C 0.17931(13) 0.3095(3) 0.13828(11) 0.0539(5) Uani 1 d . . 1 . . . H15 H 0.1563 0.3402 0.0985 0.065 Uiso 1 calc . . 1 R . . C8 C -0.20211(15) 0.4040(4) 0.11994(12) 0.0677(7) Uani 1 d . . 1 . . . H8 H -0.2342 0.4796 0.1292 0.081 Uiso 1 calc . . 1 R . . C19 C 0.17027(13) 0.2034(3) 0.22913(10) 0.0535(6) Uani 1 d . . 1 . . . H19 H 0.1409 0.1638 0.2504 0.064 Uiso 1 calc . . 1 R . . C13 C 0.03612(15) 0.5060(3) 0.17746(13) 0.0628(7) Uani 1 d . . 1 . . . H13A H 0.0310 0.5131 0.2157 0.094 Uiso 1 calc . . 1 GR . . H13B H 0.0084 0.5970 0.1527 0.094 Uiso 1 calc . . 1 GR . . H13C H 0.0893 0.5136 0.1825 0.094 Uiso 1 calc . . 1 GR . . C18 C 0.24860(13) 0.2178(3) 0.25649(12) 0.0599(6) Uani 1 d . . 1 . . . H18 H 0.2721 0.1865 0.2962 0.072 Uiso 1 calc . . 1 R . . C5 C -0.21444(14) 0.0039(3) 0.03718(11) 0.0607(6) Uani 1 d . . 1 . . . H5 H -0.2670 -0.0164 0.0217 0.073 Uiso 1 calc . . 1 R . . C7 C -0.23314(14) 0.2659(4) 0.08657(11) 0.0615(6) Uani 1 d . . 1 . . . H7 H -0.2859 0.2488 0.0729 0.074 Uiso 1 calc . . 1 R . . C4 C -0.16575(16) -0.1051(3) 0.02568(12) 0.0677(7) Uani 1 d . . 1 . . . H4 H -0.1859 -0.1983 0.0016 0.081 Uiso 1 calc . . 1 R . . I2 I 0.0000 0.92943(3) 0.2500 0.04629(7) Uani 1 d . . 2 S T P I1 I 0.0000 0.5000 0.0000 0.08320(11) Uani 1 d . . 2 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 0.0472(9) 0.0317(9) 0.0457(9) -0.0029(7) 0.0209(8) 0.0001(7) N2 0.0465(9) 0.0340(9) 0.0450(9) -0.0059(7) 0.0189(7) -0.0032(7) C2 0.0498(11) 0.0364(11) 0.0399(10) -0.0007(9) 0.0181(9) -0.0044(9) C14 0.0448(11) 0.0344(10) 0.0538(12) -0.0020(9) 0.0225(9) -0.0030(9) C11 0.0473(11) 0.0328(10) 0.0418(10) 0.0001(8) 0.0214(9) -0.0017(8) C1 0.0465(11) 0.0369(11) 0.0359(10) 0.0038(8) 0.0158(8) -0.0004(9) C6 0.0481(12) 0.0513(13) 0.0438(11) 0.0051(10) 0.0147(9) -0.0030(10) C10 0.0456(11) 0.0380(11) 0.0397(10) -0.0001(8) 0.0157(8) 0.0026(9) C9 0.0563(13) 0.0517(14) 0.0624(14) -0.0117(11) 0.0213(11) 0.0073(11) C16 0.0565(14) 0.0549(15) 0.0879(18) 0.0031(13) 0.0465(14) -0.0061(11) C3 0.0645(14) 0.0446(13) 0.0630(14) -0.0142(11) 0.0248(12) -0.0088(11) C17 0.0425(12) 0.0458(13) 0.0882(18) -0.0006(13) 0.0256(12) -0.0049(10) C12 0.0581(14) 0.0422(13) 0.0812(17) -0.0121(12) 0.0297(13) 0.0054(11) C15 0.0595(14) 0.0528(13) 0.0589(13) 0.0051(11) 0.0329(11) 0.0007(11) C8 0.0544(14) 0.0714(18) 0.0786(17) -0.0062(14) 0.0257(13) 0.0167(13) C19 0.0474(12) 0.0584(14) 0.0575(13) 0.0071(11) 0.0221(10) -0.0122(11) C13 0.0639(15) 0.0439(13) 0.0825(18) -0.0259(12) 0.0287(13) -0.0089(11) C18 0.0483(12) 0.0627(15) 0.0638(14) 0.0080(12) 0.0144(11) -0.0087(11) C5 0.0510(13) 0.0645(16) 0.0613(14) -0.0049(12) 0.0140(11) -0.0155(12) C7 0.0441(12) 0.0718(17) 0.0666(15) 0.0034(13) 0.0176(11) 0.0038(12) C4 0.0716(17) 0.0567(16) 0.0704(16) -0.0199(13) 0.0203(13) -0.0231(13) I2 0.03913(11) 0.04804(12) 0.05832(13) 0.000 0.02556(9) 0.000 I1 0.1408(3) 0.06023(17) 0.05735(15) 0.00793(12) 0.04636(16) 0.03525(16) 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' I I -0.4742 1.8119 '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' 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 C2 N1 C12 117.23(17) . . C11 N1 C2 121.56(17) . . C11 N1 C12 121.02(18) . . C11 N2 C10 122.08(17) . . C11 N2 C13 120.39(18) . . C10 N2 C13 117.44(17) . . C1 C2 N1 117.05(17) . . C3 C2 N1 122.1(2) . . C3 C2 C1 120.8(2) . . C15 C14 C11 121.6(2) . . C19 C14 C11 118.54(18) . . C19 C14 C15 119.9(2) . . N1 C11 C14 119.33(18) . . N2 C11 N1 121.40(18) . . N2 C11 C14 119.23(17) . . C2 C1 C6 119.62(19) . . C2 C1 C10 120.86(18) . . C10 C1 C6 119.51(19) . . C5 C6 C1 118.5(2) . . C7 C6 C1 118.5(2) . . C7 C6 C5 123.0(2) . . C1 C10 N2 116.75(17) . . C9 C10 N2 122.71(19) . . C9 C10 C1 120.5(2) . . C10 C9 H9 120.3 . . C10 C9 C8 119.3(2) . . C8 C9 H9 120.3 . . C17 C16 H16 119.5 . . C17 C16 C15 120.9(2) . . C15 C16 H16 119.5 . . C2 C3 H3 120.7 . . C2 C3 C4 118.6(2) . . C4 C3 H3 120.7 . . C16 C17 H17 120.1 . . C16 C17 C18 119.8(2) . . C18 C17 H17 120.1 . . N1 C12 H12A 109.5 . . N1 C12 H12B 109.5 . . N1 C12 H12C 109.5 . . H12A C12 H12B 109.5 . . H12A C12 H12C 109.5 . . H12B C12 H12C 109.5 . . C14 C15 H15 120.5 . . C16 C15 C14 119.0(2) . . C16 C15 H15 120.5 . . C9 C8 H8 119.1 . . C7 C8 C9 121.9(2) . . C7 C8 H8 119.1 . . C14 C19 H19 120.1 . . C18 C19 C14 119.8(2) . . C18 C19 H19 120.1 . . N2 C13 H13A 109.5 . . N2 C13 H13B 109.5 . . N2 C13 H13C 109.5 . . H13A C13 H13B 109.5 . . H13A C13 H13C 109.5 . . H13B C13 H13C 109.5 . . C17 C18 C19 120.6(2) . . C17 C18 H18 119.7 . . C19 C18 H18 119.7 . . C6 C5 H5 119.9 . . C4 C5 C6 120.1(2) . . C4 C5 H5 119.9 . . C6 C7 H7 119.9 . . C8 C7 C6 120.2(2) . . C8 C7 H7 119.9 . . C3 C4 H4 118.8 . . C5 C4 C3 122.3(2) . . C5 C4 H4 118.8 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C2 1.418(3) . N1 C11 1.333(3) . N1 C12 1.469(3) . N2 C11 1.331(3) . N2 C10 1.413(3) . N2 C13 1.473(3) . C2 C1 1.408(3) . C2 C3 1.374(3) . C14 C11 1.483(3) . C14 C15 1.392(3) . C14 C19 1.386(3) . C1 C6 1.416(3) . C1 C10 1.410(3) . C6 C5 1.411(3) . C6 C7 1.410(3) . C10 C9 1.370(3) . C9 H9 0.9300 . C9 C8 1.397(4) . C16 H16 0.9300 . C16 C17 1.370(4) . C16 C15 1.384(3) . C3 H3 0.9300 . C3 C4 1.403(4) . C17 H17 0.9300 . C17 C18 1.372(3) . C12 H12A 0.9600 . C12 H12B 0.9600 . C12 H12C 0.9600 . C15 H15 0.9300 . C8 H8 0.9300 . C8 C7 1.357(4) . C19 H19 0.9300 . C19 C18 1.377(3) . C13 H13A 0.9600 . C13 H13B 0.9600 . C13 H13C 0.9600 . C18 H18 0.9300 . C5 H5 0.9300 . C5 C4 1.354(4) . C7 H7 0.9300 . C4 H4 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 N1 C2 C1 C6 -176.75(17) . . . . N1 C2 C1 C10 3.3(3) . . . . N1 C2 C3 C4 178.4(2) . . . . N2 C10 C9 C8 -178.8(2) . . . . C2 N1 C11 N2 -0.6(3) . . . . C2 N1 C11 C14 177.19(17) . . . . C2 C1 C6 C5 -1.9(3) . . . . C2 C1 C6 C7 178.2(2) . . . . C2 C1 C10 N2 0.7(3) . . . . C2 C1 C10 C9 -179.3(2) . . . . C2 C3 C4 C5 -1.6(4) . . . . C14 C19 C18 C17 0.7(4) . . . . C11 N1 C2 C1 -3.5(3) . . . . C11 N1 C2 C3 178.2(2) . . . . C11 N2 C10 C1 -5.0(3) . . . . C11 N2 C10 C9 174.9(2) . . . . C11 C14 C15 C16 -178.9(2) . . . . C11 C14 C19 C18 178.3(2) . . . . C1 C2 C3 C4 0.2(3) . . . . C1 C6 C5 C4 0.6(4) . . . . C1 C6 C7 C8 1.1(4) . . . . C1 C10 C9 C8 1.0(4) . . . . C6 C1 C10 N2 -179.25(17) . . . . C6 C1 C10 C9 0.8(3) . . . . C6 C5 C4 C3 1.2(4) . . . . C10 N2 C11 N1 5.0(3) . . . . C10 N2 C11 C14 -172.76(17) . . . . C10 C1 C6 C5 178.0(2) . . . . C10 C1 C6 C7 -1.9(3) . . . . C10 C9 C8 C7 -1.9(4) . . . . C9 C8 C7 C6 0.8(4) . . . . C16 C17 C18 C19 0.1(4) . . . . C3 C2 C1 C6 1.5(3) . . . . C3 C2 C1 C10 -178.4(2) . . . . C17 C16 C15 C14 0.6(4) . . . . C12 N1 C2 C1 171.59(19) . . . . C12 N1 C2 C3 -6.7(3) . . . . C12 N1 C11 N2 -175.5(2) . . . . C12 N1 C11 C14 2.2(3) . . . . C15 C14 C11 N1 82.5(3) . . . . C15 C14 C11 N2 -99.7(2) . . . . C15 C14 C19 C18 -0.9(4) . . . . C15 C16 C17 C18 -0.8(4) . . . . C19 C14 C11 N1 -96.7(2) . . . . C19 C14 C11 N2 81.1(3) . . . . C19 C14 C15 C16 0.2(3) . . . . C13 N2 C11 N1 -171.7(2) . . . . C13 N2 C11 C14 10.6(3) . . . . C13 N2 C10 C1 171.82(19) . . . . C13 N2 C10 C9 -8.3(3) . . . . C5 C6 C7 C8 -178.8(2) . . . . C7 C6 C5 C4 -179.5(2) . . . .