Crystal structure of fipronil.
Park, Hyunjin; Kim, Jineun; Kwon, Eunjin; Kim, Tae Ho; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1472–1474; doi:10.1107/S205698901701310X

data_2311429
_publ_section_title
;
 Crystal structure of fipronil.
;
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1472
_journal_page_last               1474
_journal_paper_doi               10.1107/S205698901701310X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C12 H4 Cl2 F6 N4 O S'
_chemical_formula_moiety         'C12 H4 Cl2 F6 N4 O S'
_chemical_formula_sum            'C12 H4 Cl2 F6 N4 O S'
_chemical_formula_weight         437.15
_chemical_name_common            fipronil
_chemical_name_systematic
5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethane)sulfinyl]-1<i>H</i>-pyrazole-3-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 129.699(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.5649(16)
_cell_length_b                   12.6823(9)
_cell_length_c                   14.9051(11)
_cell_measurement_reflns_used    2101
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.62
_cell_measurement_theta_min      2.35
_cell_volume                     3281.9(4)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14125
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.441
_diffrn_reflns_theta_min         1.989
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3731
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0463P)^2^+0.8977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2506
_reflns_number_total             3731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sj5534sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2311429
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.977
_shelx_hkl_checksum              93749
_shelx_res_checksum              92426