The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
Chen, Lianqing; Tian, Lijun; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 1177–1179; doi:10.1515/ncrs-2019-0310

data_8105970
_publ_section_title
;
 The crystal structure of
 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide,
 C12H6N4Cl2F6O3S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              1177
_journal_page_last               1179
_journal_paper_doi               10.1515/ncrs-2019-0310
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C12 H6 Cl2 F6 N4 O3 S'
_chemical_formula_sum            'C12 H6 Cl2 F6 N4 O3 S'
_chemical_formula_weight         471.17
_chemical_name_systematic
;
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-<i>H<i>-pyrazole-3-carboxamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.7340(10)
_cell_length_b                   9.4010(10)
_cell_length_c                   19.2330(10)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      22
_cell_measurement_theta_min      2
_cell_volume                     3387.3(4)
_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      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.666
_diffrn_reflns_theta_min         2.174
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         6747
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0401P)^2^+0.9328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                5379
_reflns_number_total             6747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0310_suppl.cif
_cod_data_source_block           exp_1115
_cod_database_code               8105970
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.51(11)
 0.49(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F12A)
\\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F11A) \\sim Ueq: with sigma of 0.002
and sigma for terminal atoms of 0.004
Uanis(F6) \\sim Ueq, Uanis(F4) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 F10, F10A, F11, F11A, F12, F12A, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C21(H21), C24(H24)
6.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4A,H4B), N7(H7A,H7B), N8(H8A,H8B)
;
_shelx_res_checksum              40194