#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204980.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204980 loop_ _publ_author_name 'Malathy Sony, S. M.' 'Charles, P.' 'Ponnuswamy, M. N.' 'Yathirajan, H. S.' 'Nethaji, M.' _publ_section_title 4'-{[2-(But-2-enyl)-4-chloro-5-formyl-1H-imidazol-1-yl]methyl}biphenyl-2-carbonitrile _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o25 _journal_page_last o26 _journal_paper_doi 10.1107/S1600536804031186 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C22 H18 Cl N3 O' _chemical_formula_moiety 'C22 H18 Cl N3 O' _chemical_formula_sum 'C22 H18 Cl N3 O' _chemical_formula_weight 375.84 _chemical_name_systematic ; 4'-{[2-(But-2-enyl)-4-chloro-5-formyl-1H-imidazol-1-yl]methyl}biphenyl- 2-carbonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.476(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.080(6) _cell_length_b 22.782(15) _cell_length_c 10.055(7) _cell_measurement_reflns_used 20332 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.36 _cell_measurement_theta_min 1.79 _cell_volume 1961(2) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics ; PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1998) ; _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.909 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 20332 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.36 _diffrn_reflns_theta_min 1.79 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular block' _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.644 _refine_diff_density_min -0.363 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 4143 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0636 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0786P)^2^+1.127P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1695 _refine_ls_wR_factor_ref 0.1836 _reflns_number_gt 3164 _reflns_number_total 4143 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6311.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0786P)^2^+1.127P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0786P)^2^+1.127P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2204980 _cod_database_fobs_code 2204980 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl1 0.19878(12) 0.31350(4) 0.20636(13) 0.1148(4) Uani d . 1 Cl N1 -0.0161(2) 0.17227(8) 0.0377(2) 0.0525(5) Uani d . 1 N C2 -0.0731(3) 0.21374(10) -0.0613(3) 0.0573(6) Uani d . 1 C N3 -0.0097(3) 0.26607(9) -0.0196(3) 0.0694(6) Uani d . 1 N C4 0.0910(3) 0.25652(12) 0.1095(3) 0.0710(8) Uani d . 1 C C5 0.0930(3) 0.19910(12) 0.1523(3) 0.0624(7) Uani d . 1 C C6 -0.0606(3) 0.10948(10) 0.0240(3) 0.0531(6) Uani d . 1 C H6A -0.1727 0.1062 -0.0218 0.064 Uiso calc R 1 H H6B -0.0346 0.0923 0.1173 0.064 Uiso calc R 1 H C7 0.0212(2) 0.07553(9) -0.0601(2) 0.0462(5) Uani d . 1 C C8 0.1806(3) 0.06442(10) -0.0054(3) 0.0526(5) Uani d . 1 C H8 0.2380 0.0784 0.0837 0.063 Uiso calc R 1 H C9 0.2549(3) 0.03282(11) -0.0818(2) 0.0531(6) Uani d . 1 C H9 0.3618 0.0259 -0.0432 0.064 Uiso calc R 1 H C10 0.1731(2) 0.01116(9) -0.2151(2) 0.0459(5) Uani d . 1 C C11 0.0127(3) 0.02188(10) -0.2686(2) 0.0529(6) Uani d . 1 C H11 -0.0454 0.0074 -0.3571 0.063 Uiso calc R 1 H C12 -0.0611(3) 0.05374(10) -0.1921(3) 0.0542(6) Uani d . 1 C H12 -0.1680 0.0606 -0.2301 0.065 Uiso calc R 1 H C13 0.2509(3) -0.02439(9) -0.2962(2) 0.0487(5) Uani d . 1 C C14 0.3985(3) -0.00997(10) -0.3037(3) 0.0540(6) Uani d . 1 C C15 0.4723(3) -0.04597(12) -0.3754(3) 0.0654(7) Uani d . 1 C H15 0.5713 -0.0364 -0.3768 0.078 Uiso calc R 1 H C16 0.3984(4) -0.09527(12) -0.4433(3) 0.0731(8) Uani d . 1 C H16 0.4470 -0.1194 -0.4908 0.088 Uiso calc R 1 H C17 0.2511(4) -0.10905(11) -0.4410(3) 0.0682(7) Uani d . 1 C H17 0.1996 -0.1419 -0.4895 0.082 Uiso calc R 1 H C18 0.1793(3) -0.07459(11) -0.3674(3) 0.0579(6) Uani d . 1 C H18 0.0811 -0.0852 -0.3655 0.069 Uiso calc R 1 H C19 0.4756(3) 0.04398(12) -0.2454(3) 0.0623(6) Uani d . 1 C N20 0.5397(3) 0.08660(12) -0.2038(3) 0.0889(8) Uani d . 1 N C21 -0.1938(3) 0.20273(13) -0.2005(3) 0.0733(8) Uani d . 1 C H21A -0.2667 0.1735 -0.1898 0.088 Uiso calc R 1 H H21B -0.1441 0.1871 -0.2646 0.088 Uiso calc R 1 H C22 -0.2829(5) 0.25785(17) -0.2638(5) 0.1240(17) Uani d . 1 C H22 -0.2435 0.2941 -0.2261 0.149 Uiso calc R 1 H C23 -0.4159(6) 0.2557(2) -0.3717(7) 0.152(2) Uani d . 1 C H23 -0.4566 0.2202 -0.4135 0.182 Uiso calc R 1 H C24 -0.4982(6) 0.3126(2) -0.4238(5) 0.1250(16) Uani d . 1 C H24A -0.5890 0.3053 -0.5046 0.187 Uiso calc R 1 H H24B -0.4290 0.3386 -0.4495 0.187 Uiso calc R 1 H H24C -0.5291 0.3303 -0.3505 0.187 Uiso calc R 1 H C25 0.1837(4) 0.17244(16) 0.2840(3) 0.0768(8) Uani d . 1 C H25 0.2479 0.1973 0.3522 0.092 Uiso calc R 1 H O26 0.1855(3) 0.12116(11) 0.3156(2) 0.0879(7) Uani d . 1 O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.1030(7) 0.0747(6) 0.1431(9) -0.0228(5) 0.0095(6) -0.0381(6) N1 0.0501(10) 0.0444(10) 0.0648(12) 0.0013(8) 0.0217(9) -0.0054(9) C2 0.0540(13) 0.0439(12) 0.0751(16) 0.0018(10) 0.0231(12) -0.0007(11) N3 0.0644(13) 0.0457(11) 0.0936(17) -0.0042(10) 0.0203(13) -0.0046(11) C4 0.0609(16) 0.0551(15) 0.092(2) -0.0053(12) 0.0196(15) -0.0194(14) C5 0.0541(14) 0.0586(15) 0.0729(17) 0.0039(11) 0.0192(12) -0.0119(12) C6 0.0550(13) 0.0438(12) 0.0657(15) -0.0012(10) 0.0272(11) 0.0019(10) C7 0.0488(12) 0.0360(10) 0.0561(13) -0.0001(9) 0.0206(10) 0.0053(9) C8 0.0515(12) 0.0533(13) 0.0500(13) 0.0007(10) 0.0131(10) -0.0038(10) C9 0.0456(12) 0.0554(13) 0.0551(13) 0.0057(10) 0.0126(10) 0.0002(10) C10 0.0510(12) 0.0361(10) 0.0515(12) 0.0009(9) 0.0182(10) 0.0047(9) C11 0.0517(12) 0.0502(13) 0.0518(13) -0.0007(10) 0.0107(10) -0.0019(10) C12 0.0442(12) 0.0503(13) 0.0645(15) 0.0029(10) 0.0134(11) 0.0023(11) C13 0.0574(13) 0.0410(11) 0.0477(12) 0.0042(10) 0.0177(10) 0.0064(9) C14 0.0589(14) 0.0453(12) 0.0604(14) 0.0049(10) 0.0235(11) 0.0053(10) C15 0.0728(16) 0.0588(15) 0.0743(17) 0.0116(13) 0.0375(14) 0.0068(13) C16 0.107(2) 0.0526(15) 0.0717(18) 0.0185(15) 0.0457(17) 0.0014(13) C17 0.099(2) 0.0457(13) 0.0621(16) 0.0007(13) 0.0292(15) -0.0041(11) C18 0.0700(15) 0.0480(13) 0.0562(14) -0.0035(11) 0.0217(12) 0.0003(10) C19 0.0530(14) 0.0602(15) 0.0808(18) -0.0002(12) 0.0319(13) -0.0017(13) N20 0.0703(15) 0.0760(17) 0.129(2) -0.0201(14) 0.0442(16) -0.0221(16) C21 0.0717(17) 0.0584(16) 0.0800(19) -0.0056(13) 0.0123(15) 0.0071(14) C22 0.100(3) 0.070(2) 0.151(4) -0.0069(19) -0.027(3) 0.033(2) C23 0.108(3) 0.091(3) 0.206(6) 0.012(3) -0.014(4) 0.031(3) C24 0.120(3) 0.118(3) 0.115(3) 0.039(3) 0.009(3) 0.026(3) C25 0.0699(18) 0.083(2) 0.0720(19) 0.0087(15) 0.0163(15) -0.0148(16) O26 0.0929(16) 0.0888(17) 0.0761(14) 0.0209(12) 0.0202(12) 0.0049(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 '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 C2 N1 C5 107.3(2) C2 N1 C6 125.8(2) C5 N1 C6 126.9(2) N3 C2 N1 112.2(2) N3 C2 C21 123.7(2) N1 C2 C21 124.1(2) C2 N3 C4 104.2(2) C5 C4 N3 113.1(2) C5 C4 Cl1 126.5(2) N3 C4 Cl1 120.3(2) C4 C5 N1 103.2(2) C4 C5 C25 129.2(3) N1 C5 C25 127.6(3) N1 C6 C7 112.11(18) N1 C6 H6A 109.2 C7 C6 H6A 109.2 N1 C6 H6B 109.2 C7 C6 H6B 109.2 H6A C6 H6B 107.9 C12 C7 C8 118.3(2) C12 C7 C6 120.9(2) C8 C7 C6 120.9(2) C9 C8 C7 120.8(2) C9 C8 H8 119.6 C7 C8 H8 119.6 C10 C9 C8 121.2(2) C10 C9 H9 119.4 C8 C9 H9 119.4 C9 C10 C11 117.7(2) C9 C10 C13 121.6(2) C11 C10 C13 120.6(2) C12 C11 C10 120.9(2) C12 C11 H11 119.5 C10 C11 H11 119.5 C7 C12 C11 121.1(2) C7 C12 H12 119.4 C11 C12 H12 119.4 C18 C13 C14 117.1(2) C18 C13 C10 120.3(2) C14 C13 C10 122.6(2) C15 C14 C13 121.2(2) C15 C14 C19 117.3(2) C13 C14 C19 121.4(2) C16 C15 C14 119.9(3) C16 C15 H15 120.1 C14 C15 H15 120.1 C15 C16 C17 119.6(2) C15 C16 H16 120.2 C17 C16 H16 120.2 C16 C17 C18 120.8(3) C16 C17 H17 119.6 C18 C17 H17 119.6 C13 C18 C17 121.3(3) C13 C18 H18 119.3 C17 C18 H18 119.3 N20 C19 C14 176.9(3) C2 C21 C22 112.3(3) C2 C21 H21A 109.1 C22 C21 H21A 109.1 C2 C21 H21B 109.1 C22 C21 H21B 109.1 H21A C21 H21B 107.9 C23 C22 C21 121.7(4) C23 C22 H22 119.2 C21 C22 H22 119.2 C22 C23 C24 117.7(4) C22 C23 H23 121.2 C24 C23 H23 121.2 C23 C24 H24A 109.5 C23 C24 H24B 109.5 H24A C24 H24B 109.5 C23 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 O26 C25 C5 127.0(3) O26 C25 H25 116.5 C5 C25 H25 116.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C4 1.719(3) N1 C2 1.345(3) N1 C5 1.386(3) N1 C6 1.480(3) C2 N3 1.329(3) C2 C21 1.483(4) N3 C4 1.333(4) C4 C5 1.375(4) C5 C25 1.440(4) C6 C7 1.511(3) C6 H6A 0.9700 C6 H6B 0.9700 C7 C12 1.380(3) C7 C8 1.390(3) C8 C9 1.382(3) C8 H8 0.9300 C9 C10 1.388(3) C9 H9 0.9300 C10 C11 1.396(3) C10 C13 1.485(3) C11 C12 1.383(3) C11 H11 0.9300 C12 H12 0.9300 C13 C18 1.390(3) C13 C14 1.406(3) C14 C15 1.401(4) C14 C19 1.439(4) C15 C16 1.369(4) C15 H15 0.9300 C16 C17 1.382(4) C16 H16 0.9300 C17 C18 1.382(4) C17 H17 0.9300 C18 H18 0.9300 C19 N20 1.137(4) C21 C22 1.514(4) C21 H21A 0.9700 C21 H21B 0.9700 C22 C23 1.328(6) C22 H22 0.9300 C23 C24 1.500(6) C23 H23 0.9300 C24 H24A 0.9600 C24 H24B 0.9600 C24 H24C 0.9600 C25 O26 1.209(4) C25 H25 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C6 H6B O26 1_555 0.97 2.40 3.048(3) 124 y C8 H8 O26 1_555 0.93 2.71 3.463(4) 139 y C21 H21A N20 1_455 0.97 2.62 3.578(5) 170 y C6 H6A N20 1_455 0.97 2.68 3.625(4) 165 y C15 H15 O26 3_655 0.93 2.84 3.421(4) 122 y C17 H17 N3 2_544 0.93 2.74 3.532(4) 144 y C18 H18 O26 3_555 0.93 2.76 3.677(5) 171 y C24 H24A Cl1 1_454 0.96 2.91 3.818(5) 159 y C11 H11 Cg 3_556 0.93 3.27 3.98 135 y 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 C5 N1 C2 N3 -0.3(3) C6 N1 C2 N3 -179.2(2) C5 N1 C2 C21 -179.8(2) C6 N1 C2 C21 1.3(4) N1 C2 N3 C4 0.5(3) C21 C2 N3 C4 179.9(3) C2 N3 C4 C5 -0.4(3) C2 N3 C4 Cl1 -178.9(2) N3 C4 C5 N1 0.2(3) Cl1 C4 C5 N1 178.6(2) N3 C4 C5 C25 -179.0(3) Cl1 C4 C5 C25 -0.7(5) C2 N1 C5 C4 0.0(3) C6 N1 C5 C4 178.9(2) C2 N1 C5 C25 179.4(3) C6 N1 C5 C25 -1.8(4) C2 N1 C6 C7 79.6(3) C5 N1 C6 C7 -99.0(3) N1 C6 C7 C12 -111.2(2) N1 C6 C7 C8 70.2(3) C12 C7 C8 C9 0.6(3) C6 C7 C8 C9 179.3(2) C7 C8 C9 C10 -0.1(4) C8 C9 C10 C11 -0.6(3) C8 C9 C10 C13 -178.1(2) C9 C10 C11 C12 0.9(3) C13 C10 C11 C12 178.4(2) C8 C7 C12 C11 -0.3(3) C6 C7 C12 C11 -179.0(2) C10 C11 C12 C7 -0.5(4) C9 C10 C13 C18 136.4(2) C11 C10 C13 C18 -40.9(3) C9 C10 C13 C14 -42.7(3) C11 C10 C13 C14 139.9(2) C18 C13 C14 C15 -2.4(3) C10 C13 C14 C15 176.8(2) C18 C13 C14 C19 173.9(2) C10 C13 C14 C19 -6.9(4) C13 C14 C15 C16 2.0(4) C19 C14 C15 C16 -174.5(3) C14 C15 C16 C17 0.2(4) C15 C16 C17 C18 -1.9(4) C14 C13 C18 C17 0.7(3) C10 C13 C18 C17 -178.5(2) C16 C17 C18 C13 1.4(4) C15 C14 C19 N20 26(6) C13 C14 C19 N20 -150(6) N3 C2 C21 C22 -23.2(4) N1 C2 C21 C22 156.2(3) C2 C21 C22 C23 -165.5(5) C21 C22 C23 C24 178.0(5) C4 C5 C25 O26 -177.4(3) N1 C5 C25 O26 3.5(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21173722 2 PubChem 139067359