The synthesis and crystal structure of N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide, C20H10N4Cl2F6O2S
Chen, Lianqing; Tang, Chenglong; Long, Zhang; Wu, Zhongda; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 721–723; doi:10.1515/ncrs-2019-0919

data_8105267
_publ_section_title
;
 The synthesis and crystal structure of
 N-(3-cyano-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfinyl)-1H-pyrazol-5-yl)-2-phenylacetamide,
 C20H10N4Cl2F6O2S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              721
_journal_page_last               723
_journal_paper_doi               10.1515/ncrs-2019-0919
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C20 H10 Cl2 F6 N4 O2 S'
_chemical_formula_sum            'C20 H10 Cl2 F6 N4 O2 S'
_chemical_formula_weight         555.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 114.297(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5523(17)
_cell_length_b                   16.120(2)
_cell_length_c                   13.0228(18)
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.803
_cell_measurement_theta_min      2.311
_cell_volume                     2210.3(5)
_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      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13018
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.574
_diffrn_reflns_theta_min         2.131
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_refine_diff_density_max         1.695
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.094
_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   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4977
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0578
_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^)+(0.0839P)^2^+3.2295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1519
_refine_ls_wR_factor_ref         0.1699
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3585
_reflns_number_total             4977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0919_suppl.cif
_cod_data_source_block           clq50_0m
_cod_database_code               8105267
_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)
;