#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/46/2204628.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_2204628 loop_ _publ_author_name 'Fengke Yang' 'Hailian Xiao' 'Fangfang Jian' _publ_section_title ; Methyl 4-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]benzoate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2266 _journal_page_last o2267 _journal_paper_doi 10.1107/S1600536804027084 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H19 Cl N2 O3' _chemical_formula_moiety 'C17 H19 Cl N2 O3' _chemical_formula_sum 'C17 H19 Cl N2 O3' _chemical_formula_weight 334.79 _chemical_name_systematic ; Methyl 4-[(2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl)methyl]benzoate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 99.26(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.946(2) _cell_length_b 9.7085(19) _cell_length_c 15.247(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14 _cell_measurement_theta_min 4 _cell_volume 1745.3(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'NRCVAX (Gabe et al., 1989' _computing_molecular_graphics SHELXTL/PC _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL/PC (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3226 _diffrn_reflns_theta_full 25.07 _diffrn_reflns_theta_max 25.07 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.286 _refine_diff_density_min -0.208 _refine_ls_extinction_coef 0.0047(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3070 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.1216 _refine_ls_R_factor_gt 0.0586 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0459P)^2^+1.4956P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1342 _refine_ls_wR_factor_ref 0.1784 _reflns_number_gt 1705 _reflns_number_total 3070 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6384.cif _cod_data_source_block I _cod_original_cell_volume 1745.2(6) _cod_original_sg_symbol_Hall '-p 2yn' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204628 _cod_database_fobs_code 2204628 loop_ _symmetry_equiv_pos_as_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_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 0.47494(11) 0.14162(12) 0.59477(7) 0.1022(5) Uani d . 1 Cl O1 0.1915(3) 0.0439(4) 0.3706(2) 0.1134(11) Uani d . 1 O O2 0.3367(4) -0.1800(4) -0.0474(2) 0.1437(15) Uani d . 1 O O3 0.5031(4) -0.2043(3) 0.0403(2) 0.1085(10) Uani d . 1 O N1 0.5073(3) 0.3125(4) 0.4655(2) 0.0857(10) Uani d . 1 N N2 0.3664(3) 0.2608(3) 0.35546(19) 0.0707(8) Uani d . 1 N C1 0.7336(7) 0.5211(11) 0.2032(5) 0.214(4) Uani d . 1 C H1B 0.7546 0.6010 0.1725 0.321 Uiso calc R 1 H H1C 0.7166 0.4466 0.1617 0.321 Uiso calc R 1 H H1D 0.7953 0.4950 0.2486 0.321 Uiso calc R 1 H C2 0.6394(6) 0.5505(8) 0.2414(4) 0.158(3) Uani d . 1 C H2A 0.5780 0.5786 0.1953 0.189 Uiso calc R 1 H H2B 0.6566 0.6272 0.2821 0.189 Uiso calc R 1 H C3 0.5988(5) 0.4245(6) 0.2934(4) 0.131(2) Uani d . 1 C H3A 0.5850 0.3464 0.2535 0.157 Uiso calc R 1 H H3B 0.6588 0.3992 0.3414 0.157 Uiso calc R 1 H C4 0.4986(4) 0.4535(5) 0.3291(3) 0.1140(16) Uani d . 1 C H4A 0.4387 0.4760 0.2803 0.137 Uiso calc R 1 H H4B 0.5121 0.5347 0.3664 0.137 Uiso calc R 1 H C5 0.4573(4) 0.3413(4) 0.3822(3) 0.0820(11) Uani d . 1 C C6 0.4437(3) 0.2119(4) 0.4904(2) 0.0732(10) Uani d . 1 C C7 0.3548(3) 0.1745(4) 0.4261(2) 0.0686(10) Uani d . 1 C C8 0.2686(4) 0.0731(4) 0.4286(3) 0.0873(12) Uani d . 1 C H8A 0.2725 0.0240 0.4814 0.105 Uiso calc R 1 H C9 0.2941(3) 0.2599(4) 0.2676(2) 0.0823(12) Uani d . 1 C H9A 0.2995 0.3490 0.2397 0.099 Uiso calc R 1 H H9B 0.2159 0.2469 0.2755 0.099 Uiso calc R 1 H C10 0.3250(3) 0.1501(4) 0.2067(2) 0.0685(10) Uani d . 1 C C11 0.2511(3) 0.1251(5) 0.1278(3) 0.0839(12) Uani d . 1 C H11A 0.1837 0.1745 0.1152 0.101 Uiso calc R 1 H C12 0.2765(4) 0.0288(5) 0.0689(3) 0.0907(13) Uani d . 1 C H12A 0.2260 0.0133 0.0167 0.109 Uiso calc R 1 H C13 0.3759(4) -0.0459(4) 0.0852(2) 0.0793(11) Uani d . 1 C C14 0.4509(3) -0.0219(4) 0.1635(2) 0.0788(11) Uani d . 1 C H14A 0.5184 -0.0710 0.1756 0.095 Uiso calc R 1 H C15 0.4243(3) 0.0755(4) 0.2230(2) 0.0773(11) Uani d . 1 C H15A 0.4745 0.0910 0.2753 0.093 Uiso calc R 1 H C16 0.4002(5) -0.1493(5) 0.0186(3) 0.0947(13) Uani d . 1 C C17 0.5356(6) -0.3073(5) -0.0202(4) 0.143(2) Uani d . 1 C H17A 0.6109 -0.3396 0.0018 0.214 Uiso calc R 1 H H17B 0.5340 -0.2671 -0.0780 0.214 Uiso calc R 1 H H17C 0.4835 -0.3832 -0.0245 0.214 Uiso calc R 1 H 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 0.1386(11) 0.0974(8) 0.0639(6) -0.0001(7) -0.0046(6) 0.0080(6) O1 0.109(2) 0.124(3) 0.102(2) -0.029(2) 0.0004(19) -0.016(2) O2 0.161(3) 0.172(4) 0.096(2) -0.038(3) 0.015(2) -0.051(3) O3 0.157(3) 0.085(2) 0.092(2) 0.000(2) 0.043(2) -0.0120(17) N1 0.095(2) 0.077(2) 0.077(2) -0.009(2) -0.0086(18) 0.0058(18) N2 0.080(2) 0.0671(19) 0.0614(17) 0.0053(17) 0.0019(15) -0.0002(16) C1 0.171(7) 0.291(11) 0.190(8) -0.034(8) 0.057(6) 0.027(8) C2 0.148(5) 0.199(7) 0.140(5) -0.024(5) 0.063(4) 0.013(5) C3 0.133(5) 0.155(5) 0.111(4) 0.007(4) 0.044(4) 0.034(4) C4 0.113(4) 0.111(4) 0.115(4) -0.008(3) 0.009(3) 0.032(3) C5 0.092(3) 0.075(3) 0.077(3) -0.002(2) 0.004(2) 0.010(2) C6 0.091(3) 0.066(2) 0.060(2) 0.006(2) 0.003(2) -0.0031(19) C7 0.080(2) 0.062(2) 0.063(2) 0.004(2) 0.0081(18) -0.0057(18) C8 0.102(3) 0.083(3) 0.076(3) -0.009(3) 0.011(2) -0.008(2) C9 0.084(3) 0.088(3) 0.069(2) 0.016(2) -0.005(2) 0.005(2) C10 0.072(2) 0.077(2) 0.0533(19) 0.000(2) 0.0015(17) 0.0098(18) C11 0.077(3) 0.106(3) 0.065(2) 0.001(2) -0.0022(19) 0.005(2) C12 0.085(3) 0.119(4) 0.062(2) -0.019(3) -0.005(2) 0.000(3) C13 0.100(3) 0.080(3) 0.060(2) -0.024(2) 0.020(2) -0.005(2) C14 0.086(3) 0.081(3) 0.068(2) 0.003(2) 0.006(2) 0.004(2) C15 0.086(3) 0.085(3) 0.054(2) 0.007(2) -0.0068(18) 0.000(2) C16 0.114(4) 0.094(3) 0.080(3) -0.023(3) 0.028(3) -0.002(3) C17 0.235(7) 0.087(3) 0.124(4) -0.001(4) 0.081(4) -0.017(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 0.0000 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 C16 O3 C17 116.6(4) C6 N1 C5 103.6(3) C5 N2 C7 106.9(3) C5 N2 C9 127.3(3) C7 N2 C9 125.8(3) C2 C1 H1B 109.5 C2 C1 H1C 109.5 H1B C1 H1C 109.5 C2 C1 H1D 109.5 H1B C1 H1D 109.5 H1C C1 H1D 109.5 C1 C2 C3 113.0(7) C1 C2 H2A 109.0 C3 C2 H2A 109.0 C1 C2 H2B 109.0 C3 C2 H2B 109.0 H2A C2 H2B 107.8 C4 C3 C2 112.7(5) C4 C3 H3A 109.1 C2 C3 H3A 109.1 C4 C3 H3B 109.1 C2 C3 H3B 109.1 H3A C3 H3B 107.8 C3 C4 C5 115.9(5) C3 C4 H4A 108.3 C5 C4 H4A 108.3 C3 C4 H4B 108.3 C5 C4 H4B 108.3 H4A C4 H4B 107.4 N1 C5 N2 112.3(3) N1 C5 C4 122.1(4) N2 C5 C4 125.5(4) N1 C6 C7 113.8(3) N1 C6 Cl1 120.5(3) C7 C6 Cl1 125.7(3) C6 C7 N2 103.4(3) C6 C7 C8 129.9(4) N2 C7 C8 126.7(3) O1 C8 C7 127.7(4) O1 C8 H8A 116.1 C7 C8 H8A 116.1 N2 C9 C10 113.7(3) N2 C9 H9A 108.8 C10 C9 H9A 108.8 N2 C9 H9B 108.8 C10 C9 H9B 108.8 H9A C9 H9B 107.7 C15 C10 C11 118.1(4) C15 C10 C9 123.6(3) C11 C10 C9 118.3(3) C12 C11 C10 120.7(4) C12 C11 H11A 119.7 C10 C11 H11A 119.7 C11 C12 C13 121.2(4) C11 C12 H12A 119.4 C13 C12 H12A 119.4 C12 C13 C14 118.9(4) C12 C13 C16 119.2(4) C14 C13 C16 121.9(5) C15 C14 C13 119.6(4) C15 C14 H14A 120.2 C13 C14 H14A 120.2 C10 C15 C14 121.5(3) C10 C15 H15A 119.2 C14 C15 H15A 119.2 O2 C16 O3 122.9(5) O2 C16 C13 125.1(5) O3 C16 C13 112.0(4) O3 C17 H17A 109.5 O3 C17 H17B 109.5 H17A C17 H17B 109.5 O3 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C6 1.717(4) O1 C8 1.204(5) O2 C16 1.196(5) O3 C16 1.332(6) O3 C17 1.455(5) N1 C6 1.329(5) N1 C5 1.343(5) N2 C5 1.347(5) N2 C7 1.389(4) N2 C9 1.473(4) C1 C2 1.379(8) C1 H1B 0.960 C1 H1C 0.960 C1 H1D 0.960 C2 C3 1.575(8) C2 H2A 0.970 C2 H2B 0.970 C3 C4 1.421(6) C3 H3A 0.970 C3 H3B 0.970 C4 C5 1.488(6) C4 H4A 0.970 C4 H4B 0.970 C6 C7 1.373(5) C7 C8 1.429(5) C8 H8A 0.930 C9 C10 1.498(5) C9 H9A 0.970 C9 H9B 0.970 C10 C15 1.378(5) C10 C11 1.395(5) C11 C12 1.364(6) C11 H11A 0.930 C12 C13 1.379(6) C12 H12A 0.930 C13 C14 1.392(5) C13 C16 1.489(6) C14 C15 1.383(5) C14 H14A 0.930 C15 H15A 0.930 C17 H17A 0.960 C17 H17B 0.960 C17 H17C 0.960 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 C9 H9A O1 2_555 0.97 2.55 3.491(5) 165 yes C9 H9B O1 ? 0.97 2.49 2.998(5) 112 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 C1 C2 C3 C4 -177.2(6) C2 C3 C4 C5 -177.7(5) C6 N1 C5 N2 -0.6(5) C6 N1 C5 C4 177.6(4) C7 N2 C5 N1 0.8(5) C9 N2 C5 N1 -177.5(3) C7 N2 C5 C4 -177.4(4) C9 N2 C5 C4 4.4(7) C3 C4 C5 N1 75.9(6) C3 C4 C5 N2 -106.1(6) C5 N1 C6 C7 0.2(5) C5 N1 C6 Cl1 -179.3(3) N1 C6 C7 N2 0.2(4) Cl1 C6 C7 N2 179.7(3) N1 C6 C7 C8 -179.1(4) Cl1 C6 C7 C8 0.4(6) C5 N2 C7 C6 -0.6(4) C9 N2 C7 C6 177.7(3) C5 N2 C7 C8 178.8(4) C9 N2 C7 C8 -3.0(6) C6 C7 C8 O1 179.6(4) N2 C7 C8 O1 0.5(7) C5 N2 C9 C10 97.1(5) C7 N2 C9 C10 -80.8(5) N2 C9 C10 C15 -12.7(6) N2 C9 C10 C11 169.5(3) C15 C10 C11 C12 0.3(6) C9 C10 C11 C12 178.2(4) C10 C11 C12 C13 -0.3(6) C11 C12 C13 C14 0.1(6) C11 C12 C13 C16 -179.7(4) C12 C13 C14 C15 0.2(6) C16 C13 C14 C15 179.9(4) C11 C10 C15 C14 -0.1(6) C9 C10 C15 C14 -177.8(4) C13 C14 C15 C10 -0.2(6) C17 O3 C16 O2 -1.0(7) C17 O3 C16 C13 179.8(3) C12 C13 C16 O2 -4.5(7) C14 C13 C16 O2 175.7(5) C12 C13 C16 O3 174.7(4) C14 C13 C16 O3 -5.1(6) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 14143688 2 PubChem 14952880