#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:21:56 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/14/2311429.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311429
loop_
_publ_author_name
'Park, Hyunjin'
'Kim, Jineun'
'Kwon, Eunjin'
'Kim, Tae Ho'
_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]-1H-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       'φ and ω 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/[σ²(Fo²)+(0.0463P)²+0.8977P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.94088(4) 0.32995(6) 1.06637(7) 0.0429(2) Uani d 1 . .
Cl Cl2 1.04310(4) 0.06765(6) 0.90739(7) 0.0417(2) Uani d 1 . .
S S1 0.83382(4) 0.44166(6) 0.63886(6) 0.0337(2) Uani d 1 . .
F F1 0.89072(10) 0.55280(14) 0.83001(16) 0.0516(5) Uani d 1 . .
F F2 0.77293(11) 0.50457(17) 0.7312(2) 0.0695(7) Uani d 1 . .
F F3 0.80245(12) 0.62984(14) 0.66925(18) 0.0673(6) Uani d 1 . .
F F4 1.2426(3) 0.1359(8) 1.3877(5) 0.084(2) Uani d 0.620(15) A 1
F F5 1.1906(7) -0.0112(5) 1.3561(5) 0.110(4) Uani d 0.620(15) A 1
F F6 1.1641(4) 0.1123(8) 1.4199(6) 0.075(2) Uani d 0.620(15) A 1
F F4' 1.2399(5) 0.0680(16) 1.3697(9) 0.081(4) Uani d 0.380(15) A 2
F F5' 1.1577(6) -0.0083(10) 1.3614(9) 0.075(3) Uani d 0.380(15) A 2
F F6' 1.1875(10) 0.1483(11) 1.4220(10) 0.092(5) Uani d 0.380(15) A 2
O O1 0.89951(12) 0.48383(17) 0.6504(2) 0.0470(6) Uani d 1 . .
N N1 0.93791(12) 0.22985(17) 0.88474(19) 0.0279(5) Uani d 1 . .
N N2 0.86486(12) 0.18765(17) 0.8196(2) 0.0321(6) Uani d 1 . .
N N3 1.00700(13) 0.37326(19) 0.8898(2) 0.0376(6) Uani d 1 . .
H H3A 1.0499 0.3510 0.9563 0.045 Uiso calc 1 . .
H H3B 1.0072 0.4310 0.8572 0.045 Uiso calc 1 . .
N N4 0.67806(14) 0.2159(2) 0.5679(3) 0.0525(8) Uani d 1 . .
C C1 0.82489(17) 0.5375(2) 0.7227(3) 0.0398(8) Uani d 1 . .
C C2 0.86620(15) 0.3372(2) 0.7357(2) 0.0291(6) Uani d 1 . .
C C3 0.94140(15) 0.3194(2) 0.8382(2) 0.0278(6) Uani d 1 . .
C C4 0.82316(15) 0.2528(2) 0.7293(2) 0.0304(6) Uani d 1 . .
C C5 0.99688(14) 0.1918(2) 0.9991(2) 0.0268(6) Uani d 1 . .
C C6 1.00414(16) 0.2340(2) 1.0918(3) 0.0302(6) Uani d 1 . .
C C7 1.06225(16) 0.2006(2) 1.2042(2) 0.0325(7) Uani d 1 . .
H H7 1.0673 0.2297 1.2676 0.039 Uiso calc 1 . .
C C8 1.11308(15) 0.1241(2) 1.2236(2) 0.0319(7) Uani d 1 . .
C C9 1.10661(15) 0.0802(2) 1.1335(2) 0.0307(7) Uani d 1 . .
H H9 1.1411 0.0264 1.1480 0.037 Uiso calc 1 . .
C C10 1.04895(15) 0.1158(2) 1.0209(2) 0.0287(6) Uani d 1 . .
C C11 1.1763(2) 0.0878(3) 1.3460(3) 0.0481(9) Uani d 1 . .
C C12 0.74238(17) 0.2320(2) 0.6396(3) 0.0364(7) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 C2 108.69(13)
O1 S1 C1 102.58(14)
C2 S1 C1 96.30(14)
C3 N1 N2 113.4(2)
C3 N1 C5 125.6(2)
N2 N1 C5 119.7(2)
C4 N2 N1 103.1(2)
C3 N3 H3A 120.0
C3 N3 H3B 120.0
H3A N3 H3B 120.0
F3 C1 F2 108.4(3)
F3 C1 F1 107.4(3)
F2 C1 F1 107.9(3)
F3 C1 S1 110.0(2)
F2 C1 S1 110.0(2)
F1 C1 S1 112.9(2)
C3 C2 C4 104.7(2)
C3 C2 S1 127.2(2)
C4 C2 S1 128.1(2)
N3 C3 N1 122.4(2)
N3 C3 C2 132.0(3)
N1 C3 C2 105.5(2)
N2 C4 C2 113.2(2)
N2 C4 C12 119.1(3)
C2 C4 C12 127.8(3)
C10 C5 C6 119.3(3)
C10 C5 N1 121.4(3)
C6 C5 N1 119.2(2)
C7 C6 C5 120.5(3)
C7 C6 Cl1 119.7(2)
C5 C6 Cl1 119.9(2)
C6 C7 C8 119.1(3)
C6 C7 H7 120.4
C8 C7 H7 120.4
C9 C8 C7 121.6(3)
C9 C8 C11 119.3(3)
C7 C8 C11 119.1(3)
C8 C9 C10 118.9(3)
C8 C9 H9 120.6
C10 C9 H9 120.6
C9 C10 C5 120.6(3)
C9 C10 Cl2 119.8(2)
C5 C10 Cl2 119.6(2)
F6' C11 F4' 109.4(8)
F5 C11 F6 107.4(6)
F5 C11 F4 105.6(5)
F6 C11 F4 105.6(5)
F6' C11 F5' 107.5(9)
F4' C11 F5' 101.2(7)
F6' C11 C8 113.4(6)
F4' C11 C8 115.4(5)
F5 C11 C8 114.6(4)
F6 C11 C8 113.3(4)
F4 C11 C8 109.7(4)
F5' C11 C8 108.9(5)
N4 C12 C4 179.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.724(3)
Cl2 C10 1.723(3)
S1 O1 1.479(2)
S1 C2 1.739(3)
S1 C1 1.844(3)
F1 C1 1.329(3)
F2 C1 1.325(3)
F3 C1 1.321(4)
F4 C11 1.344(7)
F5 C11 1.281(7)
F6 C11 1.331(8)
F4' C11 1.265(9)
F5' C11 1.357(11)
F6' C11 1.253(13)
N1 C3 1.359(3)
N1 N2 1.379(3)
N1 C5 1.418(3)
N2 C4 1.327(3)
N3 C3 1.340(3)
N3 H3A 0.8800
N3 H3B 0.8800
N4 C12 1.144(4)
C2 C3 1.398(4)
C2 C4 1.408(4)
C4 C12 1.437(4)
C5 C10 1.388(4)
C5 C6 1.389(4)
C6 C7 1.379(4)
C7 C8 1.384(4)
C7 H7 0.9500
C8 C9 1.373(4)
C8 C11 1.500(4)
C9 C10 1.387(4)
C9 H9 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A N4 8_556 0.88 2.39 3.183(3) 150.5
N3 H3B O1 2_756 0.88 2.28 2.896(3) 127.0
C9 H9 F2 8_556 0.95 2.42 3.222(3) 142.6
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C3 N1 N2 C4 1.3(3)
C5 N1 N2 C4 169.4(2)
O1 S1 C1 F3 67.2(2)
C2 S1 C1 F3 178.0(2)
O1 S1 C1 F2 -173.4(2)
C2 S1 C1 F2 -62.6(2)
O1 S1 C1 F1 -52.8(2)
C2 S1 C1 F1 58.0(2)
O1 S1 C2 C3 24.2(3)
C1 S1 C2 C3 -81.4(3)
O1 S1 C2 C4 -156.3(3)
C1 S1 C2 C4 98.1(3)
N2 N1 C3 N3 178.6(3)
C5 N1 C3 N3 11.4(4)
N2 N1 C3 C2 -0.3(3)
C5 N1 C3 C2 -167.6(3)
C4 C2 C3 N3 -179.6(3)
S1 C2 C3 N3 0.0(5)
C4 C2 C3 N1 -0.8(3)
S1 C2 C3 N1 178.9(2)
N1 N2 C4 C2 -1.8(3)
N1 N2 C4 C12 178.8(3)
C3 C2 C4 N2 1.7(3)
S1 C2 C4 N2 -177.9(2)
C3 C2 C4 C12 -179.0(3)
S1 C2 C4 C12 1.4(5)
C3 N1 C5 C10 -96.6(3)
N2 N1 C5 C10 96.9(3)
C3 N1 C5 C6 81.4(3)
N2 N1 C5 C6 -85.1(3)
C10 C5 C6 C7 -0.2(4)
N1 C5 C6 C7 -178.2(2)
C10 C5 C6 Cl1 179.0(2)
N1 C5 C6 Cl1 1.0(4)
C5 C6 C7 C8 -0.3(4)
Cl1 C6 C7 C8 -179.5(2)
C6 C7 C8 C9 -0.5(4)
C6 C7 C8 C11 179.9(3)
C7 C8 C9 C10 1.8(4)
C11 C8 C9 C10 -178.7(3)
C8 C9 C10 C5 -2.3(4)
C8 C9 C10 Cl2 176.2(2)
C6 C5 C10 C9 1.5(4)
N1 C5 C10 C9 179.5(2)
C6 C5 C10 Cl2 -177.0(2)
N1 C5 C10 Cl2 1.0(4)
C9 C8 C11 F6' 164.8(12)
C7 C8 C11 F6' -15.6(12)
C9 C8 C11 F4' 37.5(12)
C7 C8 C11 F4' -142.9(11)
C9 C8 C11 F5 -38.1(10)
C7 C8 C11 F5 141.4(9)
C9 C8 C11 F6 -161.9(6)
C7 C8 C11 F6 17.6(6)
C9 C8 C11 F4 80.4(6)
C7 C8 C11 F4 -100.0(6)
C9 C8 C11 F5' -75.4(7)
C7 C8 C11 F5' 104.1(7)
