#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214921.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_2214921
loop_
_publ_author_name
'Li-Min He'
'Ai-Xi Hu'
'Gao Cao'
'Jun-Jun Peng'
_publ_section_title
;
 Ethyl
 2-methyl-1-(4-phenylthiazol-2-yl)-1H-benzimidazole-6-carboxylate
;
_journal_coeditor_code           XU2301
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3643
_journal_page_last               o3643
_journal_paper_doi               10.1107/S1600536807036483
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C20 H17 N3 O2 S'
_chemical_formula_moiety         'C20 H17 N3 O2 S'
_chemical_formula_sum            'C20 H17 N3 O2 S'
_chemical_formula_weight         363.44
_chemical_name_systematic
;
Ethyl 2-methyl-1-(4-phenylthiazol-2-yl)-1H-benzimidazole-6-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                109.8500(10)
_cell_angle_beta                 100.8660(10)
_cell_angle_gamma                101.9500(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4220(4)
_cell_length_b                   10.2999(6)
_cell_length_c                   12.9328(7)
_cell_measurement_reflns_used    4266
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.2
_cell_volume                     873.04(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6843
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.7
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_gt           0.037
_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/[σ²(Fo²)+(0.0501P)²+0.3963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                2789
_reflns_number_total             3373
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2301.cif
_cod_data_source_block           I
_cod_database_code               2214921
_cod_database_fobs_code          2214921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
S S1 0.15728(6) -0.11625(5) 0.37067(4) 0.02891(15) Uani d . 1
C C1 0.2904(3) 0.0828(2) 0.22862(15) 0.0288(4) Uani d . 1
C C2 0.1496(3) -0.0595(2) 0.15201(16) 0.0381(5) Uani d . 1
H H2A 0.1177 -0.0651 0.0732 0.057 Uiso calc R 1
H H2B 0.0328 -0.0702 0.1772 0.057 Uiso calc R 1
H H2C 0.2053 -0.1369 0.1551 0.057 Uiso calc R 1
C C3 0.4919(3) 0.2931(2) 0.28858(15) 0.0287(4) Uani d . 1
C C4 0.6071(3) 0.4251(2) 0.29823(16) 0.0323(4) Uani d . 1
H H4 0.6029 0.4486 0.2331 0.039 Uiso calc R 1
C C5 0.7263(3) 0.5196(2) 0.40374(16) 0.0313(4) Uani d . 1
H H5 0.8041 0.6101 0.4117 0.038 Uiso calc R 1
C C6 0.7356(3) 0.48484(19) 0.50072(15) 0.0267(4) Uani d . 1
C C7 0.6201(2) 0.35458(18) 0.49293(14) 0.0240(4) Uani d . 1
H H7 0.6245 0.3309 0.5580 0.029 Uiso calc R 1
C C8 0.4988(2) 0.26145(18) 0.38600(14) 0.0243(4) Uani d . 1
C C9 0.8658(3) 0.59264(19) 0.61240(16) 0.0288(4) Uani d . 1
C C10 0.9946(3) 0.6407(2) 0.80855(17) 0.0385(5) Uani d . 1
H H10A 0.9371 0.7189 0.8396 0.046 Uiso calc R 1
H H10B 1.1251 0.6844 0.8063 0.046 Uiso calc R 1
C C11 1.0032(4) 0.5554(3) 0.8808(2) 0.0744(9) Uani d . 1
H H11A 0.8743 0.5180 0.8863 0.112 Uiso calc R 1
H H11B 1.0887 0.6173 0.9576 0.112 Uiso calc R 1
H H11C 1.0523 0.4746 0.8462 0.112 Uiso calc R 1
C C12 0.3068(2) 0.05844(18) 0.41850(14) 0.0228(4) Uani d . 1
C C13 0.1779(2) -0.09185(19) 0.51055(15) 0.0269(4) Uani d . 1
H H13 0.1158 -0.1622 0.5346 0.032 Uiso calc R 1
C C14 0.2952(2) 0.04196(18) 0.58256(15) 0.0238(4) Uani d . 1
C C15 0.3498(2) 0.10339(19) 0.70895(14) 0.0247(4) Uani d . 1
C C16 0.3088(3) 0.0173(2) 0.76966(16) 0.0317(4) Uani d . 1
H H16 0.2450 -0.0830 0.7296 0.038 Uiso calc R 1
C C17 0.3611(3) 0.0781(2) 0.88837(17) 0.0390(5) Uani d . 1
H H17 0.3330 0.0187 0.9291 0.047 Uiso calc R 1
C C18 0.4534(3) 0.2235(3) 0.94804(17) 0.0441(5) Uani d . 1
H H18 0.4868 0.2644 1.0294 0.053 Uiso calc R 1
C C19 0.4973(3) 0.3099(2) 0.88858(17) 0.0432(5) Uani d . 1
H H19 0.5624 0.4100 0.9293 0.052 Uiso calc R 1
C C20 0.4463(3) 0.2503(2) 0.77009(16) 0.0336(4) Uani d . 1
H H20 0.4771 0.3099 0.7299 0.040 Uiso calc R 1
N N1 0.3646(2) 0.12445(15) 0.34639(12) 0.0245(3) Uani d . 1
N N2 0.3621(2) 0.18000(17) 0.19236(13) 0.0320(4) Uani d . 1
N N3 0.3666(2) 0.12749(15) 0.52841(12) 0.0241(3) Uani d . 1
O O1 0.9530(2) 0.71445(14) 0.62906(12) 0.0380(3) Uani d . 1
O O2 0.87693(19) 0.54106(14) 0.69478(11) 0.0336(3) Uani d . 1
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'
S S 0.1246 0.1234 '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
C13 S1 C12 88.61(8)
N2 C1 N1 112.84(16)
N2 C1 C2 123.53(16)
N1 C1 C2 123.60(16)
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N2 C3 C4 129.56(16)
N2 C3 C8 110.72(16)
C4 C3 C8 119.72(17)
C5 C4 C3 118.58(16)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 121.16(17)
C4 C5 H5 119.4
C6 C5 H5 119.4
C7 C6 C5 121.03(17)
C7 C6 C9 120.57(16)
C5 C6 C9 118.36(16)
C8 C7 C6 116.93(15)
C8 C7 H7 121.5
C6 C7 H7 121.5
C7 C8 C3 122.56(16)
C7 C8 N1 132.74(15)
C3 C8 N1 104.70(15)
O1 C9 O2 122.95(18)
O1 C9 C6 124.57(17)
O2 C9 C6 112.48(15)
O2 C10 C11 106.65(17)
O2 C10 H10A 110.4
C11 C10 H10A 110.4
O2 C10 H10B 110.4
C11 C10 H10B 110.4
H10A C10 H10B 108.6
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N3 C12 N1 120.33(15)
N3 C12 S1 115.25(13)
N1 C12 S1 124.41(13)
C14 C13 S1 110.76(13)
C14 C13 H13 124.6
S1 C13 H13 124.6
C13 C14 N3 114.64(15)
C13 C14 C15 127.17(16)
N3 C14 C15 118.18(15)
C16 C15 C20 118.75(16)
C16 C15 C14 121.34(16)
C20 C15 C14 119.91(15)
C17 C16 C15 120.09(18)
C17 C16 H16 120.0
C15 C16 H16 120.0
C18 C17 C16 120.83(18)
C18 C17 H17 119.6
C16 C17 H17 119.6
C17 C18 C19 119.61(18)
C17 C18 H18 120.2
C19 C18 H18 120.2
C20 C19 C18 120.0(2)
C20 C19 H19 120.0
C18 C19 H19 120.0
C19 C20 C15 120.68(18)
C19 C20 H20 119.7
C15 C20 H20 119.7
C1 N1 C12 129.54(15)
C1 N1 C8 106.00(14)
C12 N1 C8 123.98(14)
C1 N2 C3 105.72(15)
C12 N3 C14 110.72(15)
C9 O2 C10 116.61(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C13 1.7118(18)
S1 C12 1.7348(17)
C1 N2 1.303(2)
C1 N1 1.396(2)
C1 C2 1.487(3)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 N2 1.390(2)
C3 C4 1.399(3)
C3 C8 1.399(2)
C4 C5 1.371(3)
C4 H4 0.9500
C5 C6 1.410(2)
C5 H5 0.9500
C6 C7 1.395(2)
C6 C9 1.481(3)
C7 C8 1.384(2)
C7 H7 0.9500
C8 N1 1.407(2)
C9 O1 1.211(2)
C9 O2 1.339(2)
C10 O2 1.449(2)
C10 C11 1.486(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 N3 1.292(2)
C12 N1 1.406(2)
C13 C14 1.360(2)
C13 H13 0.9500
C14 N3 1.383(2)
C14 C15 1.476(2)
C15 C16 1.395(2)
C15 C20 1.398(3)
C16 C17 1.386(3)
C16 H16 0.9500
C17 C18 1.378(3)
C17 H17 0.9500
C18 C19 1.389(3)
C18 H18 0.9500
C19 C20 1.384(3)
C19 H19 0.9500
C20 H20 0.9500
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
C13 H13 O1 1_445 0.95 2.35 3.283(2) 166
C16 H16 O1 1_445 0.95 2.44 3.307(3) 151
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
N2 C3 C4 C5 -179.36(18)
C8 C3 C4 C5 0.7(3)
C3 C4 C5 C6 0.9(3)
C4 C5 C6 C7 -1.6(3)
C4 C5 C6 C9 -179.29(16)
C5 C6 C7 C8 0.7(2)
C9 C6 C7 C8 178.32(15)
C6 C7 C8 C3 0.9(3)
C6 C7 C8 N1 -179.73(17)
N2 C3 C8 C7 178.39(16)
C4 C3 C8 C7 -1.7(3)
N2 C3 C8 N1 -1.10(19)
C4 C3 C8 N1 178.81(16)
C7 C6 C9 O1 -170.71(17)
C5 C6 C9 O1 7.0(3)
C7 C6 C9 O2 9.0(2)
C5 C6 C9 O2 -173.34(15)
C13 S1 C12 N3 0.32(14)
C13 S1 C12 N1 179.60(15)
C12 S1 C13 C14 -0.89(13)
S1 C13 C14 N3 1.30(19)
S1 C13 C14 C15 -179.55(14)
C13 C14 C15 C16 11.1(3)
N3 C14 C15 C16 -169.78(16)
C13 C14 C15 C20 -169.58(18)
N3 C14 C15 C20 9.5(2)
C20 C15 C16 C17 0.9(3)
C14 C15 C16 C17 -179.74(16)
C15 C16 C17 C18 0.1(3)
C16 C17 C18 C19 -1.0(3)
C17 C18 C19 C20 0.8(3)
C18 C19 C20 C15 0.3(3)
C16 C15 C20 C19 -1.1(3)
C14 C15 C20 C19 179.53(18)
N2 C1 N1 C12 171.17(16)
C2 C1 N1 C12 -10.8(3)
N2 C1 N1 C8 -1.0(2)
C2 C1 N1 C8 176.99(17)
N3 C12 N1 C1 -165.96(16)
S1 C12 N1 C1 14.8(2)
N3 C12 N1 C8 5.0(2)
S1 C12 N1 C8 -174.28(13)
C7 C8 N1 C1 -178.19(18)
C3 C8 N1 C1 1.23(18)
C7 C8 N1 C12 9.1(3)
C3 C8 N1 C12 -171.50(15)
N1 C1 N2 C3 0.3(2)
C2 C1 N2 C3 -177.68(17)
C4 C3 N2 C1 -179.39(19)
C8 C3 N2 C1 0.5(2)
N1 C12 N3 C14 -178.97(14)
S1 C12 N3 C14 0.34(19)
C13 C14 N3 C12 -1.1(2)
C15 C14 N3 C12 179.71(14)
O1 C9 O2 C10 2.3(3)
C6 C9 O2 C10 -177.43(15)
C11 C10 O2 C9 -173.47(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21123728
2 PubChem 68562557
