Synthesis and crystal structure of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile, C20H12N4Cl2F6O2S
Chen, Lianqing; Wu, Zhongda; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 715–717; doi:10.1515/ncrs-2019-0065

data_8105829
_publ_section_title
;
 Synthesis and crystal structure of
 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile,
 C20H12N4Cl2F6O2S
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              715
_journal_page_last               717
_journal_paper_doi               10.1515/ncrs-2019-0065
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C20 H12 Cl2 F6 N4 O2 S'
_chemical_formula_sum            'C20 H12 Cl2 F6 N4 O2 S'
_chemical_formula_weight         557.30
_chemical_name_systematic
;
1-(2,6-Dichloro-4-trifluoromethyl-phenyl)-5-(3-methoxy-benzylamino)-4-
trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.287(4)
_cell_angle_beta                 105.505(4)
_cell_angle_gamma                101.592(4)
_cell_formula_units_Z            2
_cell_length_a                   8.581(3)
_cell_length_b                   10.967(4)
_cell_length_c                   13.802(5)
_cell_measurement_reflns_used    3744
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.327
_cell_measurement_theta_min      2.536
_cell_volume                     1146.7(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_min         2.107
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4840
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.0204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3883
_reflns_number_total             4840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0065_suppl.cif
_cod_data_source_block           exp_1115
_cod_database_code               8105829
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F6A-F4A
 2.1 with sigma of 0.02
 F6A-F5A
 2.1 with sigma of 0.02
3. Rigid bond restraints
 C19, F4, F5, F6, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F5) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F4A)
\\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.01
Uanis(F5A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C14(H14), C17(H17), C20(H20)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              46638