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#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227432.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_2227432
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 Ethyl
 2-[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]-4-methylthiazole-5-carboxylate
;
_journal_coeditor_code           FJ2354
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2925
_journal_paper_doi               10.1107/S1600536810042066
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H17 Cl F N3 O2 S'
_chemical_formula_moiety         'C22 H17 Cl F N3 O2 S'
_chemical_formula_sum            'C22 H17 Cl F N3 O2 S'
_chemical_formula_weight         441.90
_chemical_name_systematic
;
Ethyl 2-[5-(4-chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]-4-
methylthiazole-5-carboxylate
;
_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                 112.9220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0296(5)
_cell_length_b                   19.4428(6)
_cell_length_c                   9.5847(3)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.93
_cell_measurement_theta_min      2.79
_cell_volume                     2064.74(13)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30630
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.8778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS, Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.526
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.244
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+9.3055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1587
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                3944
_reflns_number_total             4697
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2354.cif
_cod_data_source_block           I
_cod_original_cell_volume        2064.74(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227432
_cod_database_fobs_code          2227432
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.28859(8) 0.28472(4) -0.01128(10) 0.0162(2) Uani d . 1 . .
Cl Cl1 -0.24355(9) -0.04920(5) 0.40468(12) 0.0288(2) Uani d . 1 . .
F F1 -0.2939(2) 0.38188(13) 0.2896(3) 0.0373(6) Uani d . 1 . .
O O1 0.4449(2) 0.36177(13) -0.1138(3) 0.0239(6) Uani d . 1 . .
O O2 0.5434(2) 0.27417(14) -0.1712(3) 0.0247(6) Uani d . 1 . .
N N1 0.0936(3) 0.24138(15) 0.0961(3) 0.0161(6) Uani d . 1 . .
N N2 0.0143(3) 0.21207(15) 0.1472(3) 0.0154(6) Uani d . 1 . .
N N3 0.3202(3) 0.15335(15) 0.0001(4) 0.0176(6) Uani d . 1 . .
C C1 0.0322(3) 0.14214(17) 0.1675(4) 0.0160(7) Uani d . 1 . .
C C2 0.1269(3) 0.12630(18) 0.1269(4) 0.0165(7) Uani d . 1 . .
H H2A 0.1608 0.0832 0.1279 0.020 Uiso calc R 1 . .
C C3 0.1616(3) 0.18936(18) 0.0837(4) 0.0164(7) Uani d . 1 . .
C C4 0.2558(3) 0.20259(17) 0.0272(4) 0.0155(7) Uani d . 1 . .
C C5 0.4011(3) 0.18060(18) -0.0546(4) 0.0178(7) Uani d . 1 . .
C C6 0.3963(3) 0.25092(18) -0.0694(4) 0.0165(7) Uani d . 1 . .
C C7 0.4701(3) 0.29491(19) -0.1238(4) 0.0185(7) Uani d . 1 . .
C C8 0.5145(4) 0.4118(2) -0.1592(5) 0.0281(9) Uani d . 1 . .
H H8A 0.5329 0.3938 -0.2422 0.034 Uiso calc R 1 . .
H H8B 0.5898 0.4220 -0.0750 0.034 Uiso calc R 1 . .
C C9 0.4385(4) 0.4758(2) -0.2080(5) 0.0326(10) Uani d . 1 . .
H H9A 0.4861 0.5124 -0.2229 0.049 Uiso calc R 1 . .
H H9B 0.4099 0.4887 -0.1310 0.049 Uiso calc R 1 . .
H H9C 0.3708 0.4669 -0.3010 0.049 Uiso calc R 1 . .
C C10 0.4855(4) 0.1330(2) -0.0880(5) 0.0257(9) Uani d . 1 . .
H H10A 0.4783 0.1399 -0.1903 0.039 Uiso calc R 1 . .
H H10B 0.4654 0.0863 -0.0754 0.039 Uiso calc R 1 . .
H H10C 0.5669 0.1424 -0.0196 0.039 Uiso calc R 1 . .
C C11 -0.0686(3) 0.25574(18) 0.1786(4) 0.0150(7) Uani d . 1 . .
C C12 -0.0298(3) 0.32104(18) 0.2356(4) 0.0179(7) Uani d . 1 . .
H H12A 0.0474 0.3358 0.2498 0.021 Uiso calc R 1 . .
C C13 -0.1070(3) 0.36415(19) 0.2714(4) 0.0207(8) Uani d . 1 . .
H H13A -0.0829 0.4083 0.3082 0.025 Uiso calc R 1 . .
C C14 -0.2197(4) 0.3401(2) 0.2510(5) 0.0247(8) Uani d . 1 . .
C C15 -0.2614(3) 0.2759(2) 0.1924(5) 0.0242(8) Uani d . 1 . .
H H15A -0.3383 0.2613 0.1796 0.029 Uiso calc R 1 . .
C C16 -0.1848(3) 0.2336(2) 0.1528(4) 0.0215(8) Uani d . 1 . .
H H16A -0.2113 0.1908 0.1093 0.026 Uiso calc R 1 . .
C C17 -0.0370(3) 0.09629(17) 0.2271(4) 0.0162(7) Uani d . 1 . .
C C18 -0.0471(3) 0.10914(19) 0.3647(4) 0.0207(8) Uani d . 1 . .
H H18A -0.0105 0.1478 0.4208 0.025 Uiso calc R 1 . .
C C19 -0.1115(3) 0.06460(19) 0.4186(5) 0.0229(8) Uani d . 1 . .
H H19A -0.1185 0.0732 0.5103 0.027 Uiso calc R 1 . .
C C20 -0.1653(3) 0.00709(18) 0.3334(5) 0.0205(8) Uani d . 1 . .
C C21 -0.1571(3) -0.00729(18) 0.1970(5) 0.0217(8) Uani d . 1 . .
H H21A -0.1939 -0.0461 0.1416 0.026 Uiso calc R 1 . .
C C22 -0.0923(3) 0.03780(18) 0.1440(4) 0.0204(8) Uani d . 1 . .
H H22A -0.0858 0.0289 0.0521 0.025 Uiso calc R 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'
F F 0.0171 0.0103 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 S1 C6 . . 88.81(17) ?
C7 O1 C8 . . 116.8(3) ?
C3 N1 N2 . . 104.8(3) ?
N1 N2 C1 . . 111.8(3) ?
N1 N2 C11 . . 118.3(3) ?
C1 N2 C11 . . 129.8(3) ?
C4 N3 C5 . . 110.6(3) ?
C2 C1 N2 . . 106.4(3) ?
C2 C1 C17 . . 128.9(3) ?
N2 C1 C17 . . 124.7(3) ?
C1 C2 C3 . . 105.1(3) ?
C1 C2 H2A . . 127.4 ?
C3 C2 H2A . . 127.4 ?
N1 C3 C2 . . 111.8(3) ?
N1 C3 C4 . . 119.4(3) ?
C2 C3 C4 . . 128.7(3) ?
N3 C4 C3 . . 123.1(3) ?
N3 C4 S1 . . 115.5(3) ?
C3 C4 S1 . . 121.4(3) ?
C6 C5 N3 . . 114.5(3) ?
C6 C5 C10 . . 126.7(3) ?
N3 C5 C10 . . 118.8(3) ?
C5 C6 C7 . . 127.6(3) ?
C5 C6 S1 . . 110.6(3) ?
C7 C6 S1 . . 121.8(3) ?
O2 C7 O1 . . 124.5(3) ?
O2 C7 C6 . . 124.8(3) ?
O1 C7 C6 . . 110.7(3) ?
O1 C8 C9 . . 107.1(3) ?
O1 C8 H8A . . 110.3 ?
C9 C8 H8A . . 110.3 ?
O1 C8 H8B . . 110.3 ?
C9 C8 H8B . . 110.3 ?
H8A C8 H8B . . 108.6 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C5 C10 H10A . . 109.5 ?
C5 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C5 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C16 . . 120.9(3) ?
C12 C11 N2 . . 118.1(3) ?
C16 C11 N2 . . 121.0(3) ?
C13 C12 C11 . . 119.6(3) ?
C13 C12 H12A . . 120.2 ?
C11 C12 H12A . . 120.2 ?
C14 C13 C12 . . 118.5(4) ?
C14 C13 H13A . . 120.8 ?
C12 C13 H13A . . 120.8 ?
F1 C14 C13 . . 118.2(4) ?
F1 C14 C15 . . 118.6(4) ?
C13 C14 C15 . . 123.2(3) ?
C14 C15 C16 . . 118.1(3) ?
C14 C15 H15A . . 120.9 ?
C16 C15 H15A . . 120.9 ?
C11 C16 C15 . . 119.6(4) ?
C11 C16 H16A . . 120.2 ?
C15 C16 H16A . . 120.2 ?
C18 C17 C22 . . 119.1(3) ?
C18 C17 C1 . . 121.8(3) ?
C22 C17 C1 . . 119.0(3) ?
C19 C18 C17 . . 120.5(3) ?
C19 C18 H18A . . 119.8 ?
C17 C18 H18A . . 119.8 ?
C20 C19 C18 . . 118.9(4) ?
C20 C19 H19A . . 120.6 ?
C18 C19 H19A . . 120.6 ?
C21 C20 C19 . . 122.2(3) ?
C21 C20 Cl1 . . 119.5(3) ?
C19 C20 Cl1 . . 118.3(3) ?
C20 C21 C22 . . 118.4(3) ?
C20 C21 H21A . . 120.8 ?
C22 C21 H21A . . 120.8 ?
C21 C22 C17 . . 120.9(4) ?
C21 C22 H22A . . 119.6 ?
C17 C22 H22A . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 . 1.719(3) ?
S1 C6 . 1.727(3) ?
Cl1 C20 . 1.747(4) ?
F1 C14 . 1.360(4) ?
O1 C7 . 1.347(4) ?
O1 C8 . 1.456(4) ?
O2 C7 . 1.207(4) ?
N1 C3 . 1.334(4) ?
N1 N2 . 1.356(4) ?
N2 C1 . 1.378(4) ?
N2 C11 . 1.429(4) ?
N3 C4 . 1.319(4) ?
N3 C5 . 1.378(4) ?
C1 C2 . 1.374(5) ?
C1 C17 . 1.478(5) ?
C2 C3 . 1.408(5) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.457(5) ?
C5 C6 . 1.373(5) ?
C5 C10 . 1.498(5) ?
C6 C7 . 1.467(5) ?
C8 C9 . 1.507(6) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.389(5) ?
C11 C16 . 1.389(5) ?
C12 C13 . 1.389(5) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.375(5) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.380(6) ?
C15 C16 . 1.393(5) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
C17 C18 . 1.394(5) ?
C17 C22 . 1.399(5) ?
C18 C19 . 1.389(5) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.387(5) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.378(6) ?
C21 C22 . 1.394(5) ?
C21 H21A . 0.9300 ?
C22 H22A . 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
C15 H15A O2 4_466 0.93 2.48 3.251(5) 140.9 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C1 . . . . 0.2(4) ?
C3 N1 N2 C11 . . . . 177.3(3) ?
N1 N2 C1 C2 . . . . -0.2(4) ?
C11 N2 C1 C2 . . . . -176.9(3) ?
N1 N2 C1 C17 . . . . 177.8(3) ?
C11 N2 C1 C17 . . . . 1.1(6) ?
N2 C1 C2 C3 . . . . 0.1(4) ?
C17 C1 C2 C3 . . . . -177.8(4) ?
N2 N1 C3 C2 . . . . -0.1(4) ?
N2 N1 C3 C4 . . . . 178.5(3) ?
C1 C2 C3 N1 . . . . 0.0(4) ?
C1 C2 C3 C4 . . . . -178.5(4) ?
C5 N3 C4 C3 . . . . 179.1(3) ?
C5 N3 C4 S1 . . . . 0.0(4) ?
N1 C3 C4 N3 . . . . -174.4(3) ?
C2 C3 C4 N3 . . . . 4.0(6) ?
N1 C3 C4 S1 . . . . 4.7(5) ?
C2 C3 C4 S1 . . . . -176.9(3) ?
C6 S1 C4 N3 . . . . 0.4(3) ?
C6 S1 C4 C3 . . . . -178.8(3) ?
C4 N3 C5 C6 . . . . -0.4(5) ?
C4 N3 C5 C10 . . . . 178.2(3) ?
N3 C5 C6 C7 . . . . 179.9(3) ?
C10 C5 C6 C7 . . . . 1.4(7) ?
N3 C5 C6 S1 . . . . 0.7(4) ?
C10 C5 C6 S1 . . . . -177.8(3) ?
C4 S1 C6 C5 . . . . -0.6(3) ?
C4 S1 C6 C7 . . . . -179.8(3) ?
C8 O1 C7 O2 . . . . -2.1(6) ?
C8 O1 C7 C6 . . . . 178.0(3) ?
C5 C6 C7 O2 . . . . 3.9(6) ?
S1 C6 C7 O2 . . . . -177.0(3) ?
C5 C6 C7 O1 . . . . -176.2(4) ?
S1 C6 C7 O1 . . . . 2.9(4) ?
C7 O1 C8 C9 . . . . 154.3(4) ?
N1 N2 C11 C12 . . . . -34.4(5) ?
C1 N2 C11 C12 . . . . 142.0(4) ?
N1 N2 C11 C16 . . . . 145.5(3) ?
C1 N2 C11 C16 . . . . -38.0(5) ?
C16 C11 C12 C13 . . . . 1.8(5) ?
N2 C11 C12 C13 . . . . -178.2(3) ?
C11 C12 C13 C14 . . . . 1.0(5) ?
C12 C13 C14 F1 . . . . 178.4(3) ?
C12 C13 C14 C15 . . . . -2.1(6) ?
F1 C14 C15 C16 . . . . 179.8(3) ?
C13 C14 C15 C16 . . . . 0.3(6) ?
C12 C11 C16 C15 . . . . -3.6(6) ?
N2 C11 C16 C15 . . . . 176.5(3) ?
C14 C15 C16 C11 . . . . 2.5(6) ?
C2 C1 C17 C18 . . . . 123.4(4) ?
N2 C1 C17 C18 . . . . -54.1(5) ?
C2 C1 C17 C22 . . . . -55.6(5) ?
N2 C1 C17 C22 . . . . 126.9(4) ?
C22 C17 C18 C19 . . . . -0.2(5) ?
C1 C17 C18 C19 . . . . -179.2(3) ?
C17 C18 C19 C20 . . . . 0.2(6) ?
C18 C19 C20 C21 . . . . -0.1(6) ?
C18 C19 C20 Cl1 . . . . 178.8(3) ?
C19 C20 C21 C22 . . . . 0.0(6) ?
Cl1 C20 C21 C22 . . . . -178.9(3) ?
C20 C21 C22 C17 . . . . 0.0(6) ?
C18 C17 C22 C21 . . . . 0.1(5) ?
C1 C17 C22 C21 . . . . 179.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656219
2 PubChem 45277253
