#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229362.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_2229362
loop_
_publ_author_name
'Dai, Hong'
'Zhang, Yu-Ting'
'Shi, Yu-Jun'
'Zhang, Wen-Wen'
'Shen, Yong-Jun'
_publ_section_title
;
 (E)-3-Methyl-5-(4-methylphenoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde
 O-[(2-chloro-1,3-thiazol-5-yl)methyl]oxime
;
_journal_coeditor_code           DS2094
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o727
_journal_paper_doi               10.1107/S1600536811006702
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H19 Cl N4 O2 S'
_chemical_formula_moiety         'C22 H19 Cl N4 O2 S'
_chemical_formula_sum            'C22 H19 Cl N4 O2 S'
_chemical_formula_weight         438.92
_chemical_name_systematic
;
(E)-3-Methyl-5-(4-methylphenoxy)-1-phenyl-1H-pyrazole-4-
carbaldehyde O-[(2-chloro-1,3-thiazol-5-yl)methyl]oxime
;
_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
_cell_angle_alpha                102.700(6)
_cell_angle_beta                 107.885(6)
_cell_angle_gamma                93.634(7)
_cell_formula_units_Z            2
_cell_length_a                   8.114(3)
_cell_length_b                   11.452(4)
_cell_length_c                   12.494(4)
_cell_measurement_reflns_used    1218
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.27
_cell_measurement_theta_min      2.67
_cell_volume                     1067.1(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5562
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9683
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Triclinic
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0490
_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)+(0.0490P)²+0.1132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                2030
_reflns_number_total             3755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ds2094.cif
_cod_data_source_block           I
_cod_database_code               2229362
_cod_database_fobs_code          2229362
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.45270(11) 0.85178(9) 0.33662(8) 0.0647(3) Uani d . 1 . .
Cl Cl1 0.61728(16) 0.68418(11) 0.47383(9) 0.0975(4) Uani d . 1 . .
O O1 -0.0621(2) 0.84964(18) 0.10876(17) 0.0450(5) Uani d . 1 . .
O O2 0.4577(3) 1.0355(2) 0.16837(17) 0.0530(6) Uani d . 1 . .
N N1 -0.2014(3) 0.7626(2) -0.0923(2) 0.0434(7) Uani d . 1 . .
N N2 -0.1696(3) 0.7554(2) -0.1953(2) 0.0510(7) Uani d . 1 . .
N N3 0.2917(3) 0.9627(2) 0.1279(2) 0.0479(7) Uani d . 1 . .
N N4 0.7640(4) 0.8986(3) 0.4813(2) 0.0660(9) Uani d . 1 . .
C C1 -0.3633(4) 0.7038(3) -0.0939(3) 0.0471(8) Uani d . 1 . .
C C2 -0.4206(4) 0.7326(3) 0.0001(3) 0.0636(10) Uani d . 1 . .
H H2 -0.3572 0.7937 0.0653 0.076 Uiso calc R 1 . .
C C3 -0.5742(5) 0.6692(4) -0.0040(4) 0.0768(12) Uani d . 1 . .
H H3 -0.6126 0.6870 0.0599 0.092 Uiso calc R 1 . .
C C4 -0.6702(5) 0.5811(4) -0.0999(5) 0.0914(14) Uani d . 1 . .
H H4 -0.7723 0.5384 -0.1009 0.110 Uiso calc R 1 . .
C C5 -0.6157(5) 0.5561(4) -0.1939(4) 0.0941(14) Uani d . 1 . .
H H5 -0.6828 0.4975 -0.2602 0.113 Uiso calc R 1 . .
C C6 -0.4610(5) 0.6171(4) -0.1921(3) 0.0719(11) Uani d . 1 . .
H H6 -0.4240 0.5994 -0.2566 0.086 Uiso calc R 1 . .
C C7 0.0690(4) 0.8267(4) -0.2568(3) 0.0676(11) Uani d . 1 . .
H H7A 0.1699 0.7855 -0.2474 0.101 Uiso calc R 1 . .
H H7B 0.1031 0.9108 -0.2490 0.101 Uiso calc R 1 . .
H H7C -0.0152 0.7919 -0.3324 0.101 Uiso calc R 1 . .
C C8 -0.0104(4) 0.8142(3) -0.1657(3) 0.0465(8) Uani d . 1 . .
C C9 0.0656(4) 0.8599(3) -0.0440(2) 0.0400(8) Uani d . 1 . .
C C10 -0.0610(4) 0.8238(3) -0.0019(3) 0.0395(8) Uani d . 1 . .
C C11 -0.0066(4) 0.7658(3) 0.1735(2) 0.0408(8) Uani d . 1 . .
C C12 -0.0280(4) 0.7901(3) 0.2804(3) 0.0541(9) Uani d . 1 . .
H H12 -0.0762 0.8582 0.3055 0.065 Uiso calc R 1 . .
C C13 0.0232(4) 0.7116(3) 0.3504(3) 0.0591(10) Uani d . 1 . .
H H13 0.0085 0.7278 0.4230 0.071 Uiso calc R 1 . .
C C14 0.0945(4) 0.6111(3) 0.3161(3) 0.0531(9) Uani d . 1 . .
C C15 0.1125(4) 0.5889(3) 0.2072(3) 0.0550(9) Uani d . 1 . .
H H15 0.1606 0.5209 0.1819 0.066 Uiso calc R 1 . .
C C16 0.0612(4) 0.6647(3) 0.1352(3) 0.0449(8) Uani d . 1 . .
H H16 0.0725 0.6474 0.0617 0.054 Uiso calc R 1 . .
C C17 0.1474(5) 0.5256(4) 0.3933(3) 0.0871(13) Uani d . 1 . .
H H17A 0.2202 0.5707 0.4695 0.131 Uiso calc R 1 . .
H H17B 0.2110 0.4678 0.3609 0.131 Uiso calc R 1 . .
H H17C 0.0447 0.4841 0.3984 0.131 Uiso calc R 1 . .
C C18 0.2345(4) 0.9303(3) 0.0182(3) 0.0437(8) Uani d . 1 . .
H H18 0.3035 0.9525 -0.0233 0.052 Uiso calc R 1 . .
C C19 0.5031(4) 1.0792(3) 0.2911(3) 0.0565(9) Uani d . 1 . .
H H19A 0.4004 1.1029 0.3096 0.068 Uiso calc R 1 . .
H H19B 0.5904 1.1505 0.3175 0.068 Uiso calc R 1 . .
C C20 0.5727(4) 0.9879(3) 0.3541(3) 0.0468(8) Uani d . 1 . .
C C21 0.7309(4) 0.9944(4) 0.4334(3) 0.0606(10) Uani d . 1 . .
H H21 0.8149 1.0620 0.4548 0.073 Uiso calc R 1 . .
C C22 0.6282(5) 0.8196(4) 0.4373(3) 0.0581(10) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 S1 C20 . . 88.36(18) ?
C10 O1 C11 . . 117.5(2) ?
N3 O2 C19 . . 107.2(2) ?
C10 N1 N2 . . 110.3(2) ?
C10 N1 C1 . . 130.4(3) ?
N2 N1 C1 . . 119.3(3) ?
C8 N2 N1 . . 105.2(2) ?
C18 N3 O2 . . 110.9(2) ?
C22 N4 C21 . . 108.2(3) ?
C2 C1 C6 . . 120.4(3) ?
C2 C1 N1 . . 121.3(3) ?
C6 C1 N1 . . 118.3(3) ?
C1 C2 C3 . . 118.9(4) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 121.2(4) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C5 C4 C3 . . 119.5(4) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.7(4) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.2(4) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C8 C7 H7A . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C8 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N2 C8 C9 . . 112.1(3) ?
N2 C8 C7 . . 120.5(3) ?
C9 C8 C7 . . 127.4(3) ?
C10 C9 C8 . . 103.7(3) ?
C10 C9 C18 . . 129.1(3) ?
C8 C9 C18 . . 127.2(3) ?
N1 C10 O1 . . 122.1(3) ?
N1 C10 C9 . . 108.8(3) ?
O1 C10 C9 . . 128.9(3) ?
C16 C11 C12 . . 120.9(3) ?
C16 C11 O1 . . 124.2(3) ?
C12 C11 O1 . . 114.9(3) ?
C11 C12 C13 . . 118.9(3) ?
C11 C12 H12 . . 120.6 ?
C13 C12 H12 . . 120.6 ?
C14 C13 C12 . . 121.9(3) ?
C14 C13 H13 . . 119.0 ?
C12 C13 H13 . . 119.0 ?
C13 C14 C15 . . 117.6(3) ?
C13 C14 C17 . . 121.1(3) ?
C15 C14 C17 . . 121.3(3) ?
C16 C15 C14 . . 121.8(3) ?
C16 C15 H15 . . 119.1 ?
C14 C15 H15 . . 119.1 ?
C11 C16 C15 . . 118.9(3) ?
C11 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N3 C18 C9 . . 121.6(3) ?
N3 C18 H18 . . 119.2 ?
C9 C18 H18 . . 119.2 ?
O2 C19 C20 . . 112.5(3) ?
O2 C19 H19A . . 109.1 ?
C20 C19 H19A . . 109.1 ?
O2 C19 H19B . . 109.1 ?
C20 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C21 C20 C19 . . 128.5(3) ?
C21 C20 S1 . . 108.3(3) ?
C19 C20 S1 . . 123.1(2) ?
C20 C21 N4 . . 117.8(3) ?
C20 C21 H21 . . 121.1 ?
N4 C21 H21 . . 121.1 ?
N4 C22 S1 . . 117.4(3) ?
N4 C22 Cl1 . . 122.8(3) ?
S1 C22 Cl1 . . 119.9(2) ?
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 C22 . 1.708(4) ?
S1 C20 . 1.718(3) ?
Cl1 C22 . 1.714(4) ?
O1 C10 . 1.352(3) ?
O1 C11 . 1.397(3) ?
O2 N3 . 1.421(3) ?
O2 C19 . 1.424(3) ?
N1 C10 . 1.351(3) ?
N1 N2 . 1.375(3) ?
N1 C1 . 1.430(4) ?
N2 C8 . 1.321(4) ?
N3 C18 . 1.264(4) ?
N4 C22 . 1.272(4) ?
N4 C21 . 1.365(4) ?
C1 C2 . 1.374(4) ?
C1 C6 . 1.374(5) ?
C2 C3 . 1.383(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.362(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.358(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.497(4) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 C9 . 1.414(4) ?
C9 C10 . 1.370(4) ?
C9 C18 . 1.436(4) ?
C11 C16 . 1.368(4) ?
C11 C12 . 1.370(4) ?
C12 C13 . 1.384(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.365(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.383(4) ?
C14 C17 . 1.512(4) ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18 . 0.9300 ?
C19 C20 . 1.482(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 C21 . 1.345(4) ?
C21 H21 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 N2 C8 . . . . -0.8(3) ?
C1 N1 N2 C8 . . . . -178.1(2) ?
C19 O2 N3 C18 . . . . 173.5(3) ?
C10 N1 C1 C2 . . . . 20.1(5) ?
N2 N1 C1 C2 . . . . -163.2(3) ?
C10 N1 C1 C6 . . . . -159.8(3) ?
N2 N1 C1 C6 . . . . 16.9(4) ?
C6 C1 C2 C3 . . . . 2.8(5) ?
N1 C1 C2 C3 . . . . -177.1(3) ?
C1 C2 C3 C4 . . . . -1.3(6) ?
C2 C3 C4 C5 . . . . -1.0(7) ?
C3 C4 C5 C6 . . . . 1.8(7) ?
C2 C1 C6 C5 . . . . -2.0(5) ?
N1 C1 C6 C5 . . . . 177.9(3) ?
C4 C5 C6 C1 . . . . -0.3(6) ?
N1 N2 C8 C9 . . . . 0.4(3) ?
N1 N2 C8 C7 . . . . -179.3(3) ?
N2 C8 C9 C10 . . . . 0.0(3) ?
C7 C8 C9 C10 . . . . 179.7(3) ?
N2 C8 C9 C18 . . . . -178.4(3) ?
C7 C8 C9 C18 . . . . 1.3(5) ?
N2 N1 C10 O1 . . . . 176.1(3) ?
C1 N1 C10 O1 . . . . -7.0(5) ?
N2 N1 C10 C9 . . . . 0.8(3) ?
C1 N1 C10 C9 . . . . 177.8(3) ?
C11 O1 C10 N1 . . . . 90.5(3) ?
C11 O1 C10 C9 . . . . -95.2(4) ?
C8 C9 C10 N1 . . . . -0.5(3) ?
C18 C9 C10 N1 . . . . 177.9(3) ?
C8 C9 C10 O1 . . . . -175.4(3) ?
C18 C9 C10 O1 . . . . 3.0(5) ?
C10 O1 C11 C16 . . . . 5.4(4) ?
C10 O1 C11 C12 . . . . -173.3(3) ?
C16 C11 C12 C13 . . . . 1.2(5) ?
O1 C11 C12 C13 . . . . 179.9(3) ?
C11 C12 C13 C14 . . . . 0.1(5) ?
C12 C13 C14 C15 . . . . -0.8(5) ?
C12 C13 C14 C17 . . . . -179.2(3) ?
C13 C14 C15 C16 . . . . 0.1(5) ?
C17 C14 C15 C16 . . . . 178.6(3) ?
C12 C11 C16 C15 . . . . -1.8(4) ?
O1 C11 C16 C15 . . . . 179.6(3) ?
C14 C15 C16 C11 . . . . 1.1(5) ?
O2 N3 C18 C9 . . . . -177.5(2) ?
C10 C9 C18 N3 . . . . 4.6(5) ?
C8 C9 C18 N3 . . . . -177.4(3) ?
N3 O2 C19 C20 . . . . 79.6(3) ?
O2 C19 C20 C21 . . . . 119.4(3) ?
O2 C19 C20 S1 . . . . -62.1(3) ?
C22 S1 C20 C21 . . . . 0.0(2) ?
C22 S1 C20 C19 . . . . -178.9(3) ?
C19 C20 C21 N4 . . . . 178.9(3) ?
S1 C20 C21 N4 . . . . 0.1(4) ?
C22 N4 C21 C20 . . . . -0.2(4) ?
C21 N4 C22 S1 . . . . 0.1(4) ?
C21 N4 C22 Cl1 . . . . 179.3(2) ?
C20 S1 C22 N4 . . . . -0.1(3) ?
C20 S1 C22 Cl1 . . . . -179.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656520
