The synthesis and crystal structure of ethyl (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate, C22H15N3Cl2F6O4S
Chen, Lianqing; Zhang, Long; Tang, Chenglong; Wu, Zhongda; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 681–684; doi:10.1515/ncrs-2019-0898

data_8105256
_publ_section_title
;
 The synthesis and crystal structure of ethyl
 (E)-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-5-((2-methoxybenzylidene)amino)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carboxylate,
 C22H15N3Cl2F6O4S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              681
_journal_page_last               684
_journal_paper_doi               10.1515/ncrs-2019-0898
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C22 H15 Cl2 F6 N3 O4 S'
_chemical_formula_sum            'C22 H15 Cl2 F6 N3 O4 S'
_chemical_formula_weight         602.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 112.714(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6099(10)
_cell_length_b                   12.0571(9)
_cell_length_c                   16.2351(13)
_cell_measurement_reflns_used    9147
_cell_measurement_temperature    150.01
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.34
_cell_volume                     2457.5(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32747
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_min         2.342
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.9367.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+1.7513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3776
_reflns_number_total             5048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0898_suppl.cif
_cod_data_source_block           mo_0227_2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '__reflns_threshold_expression' was replaced with
'_reflns_threshold_expression'.

Automatic conversion script
Id: cif_correct_tags 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8105256
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.Rigid body (RIGU) restrains
 O3, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C16A)=Sof(H16c)=Sof(H16d)=Sof(C17A)=Sof(H17d)=Sof(H17e)=Sof(H17f)=1-FVAR(1)
 Sof(C16)=Sof(H16a)=Sof(H16b)=Sof(C17)=Sof(H17a)=Sof(H17b)=Sof(H17c)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C19(H19), C22(H22)
5.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C17(H17a,H17b,H17c)
 C11(H11A,H11B,H11C)
;