Crystal structure of the fluorescent fipronil derivative 5,5′-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile), C25H6N8O2Cl4F12S2
Du, Yanting; Zhou, Quan; Huang, Yufeng; Chen, Lianqing; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 665–667; doi:10.1515/ncrs-2019-0018

data_8105813
_publ_section_title
;
 Crystal structure of the fluorescent fipronil derivative
 5,5&#x2032;-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile),
 C25H6N8O2Cl4F12S2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              665
_journal_page_last               667
_journal_paper_doi               10.1515/ncrs-2019-0018
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C12.5 H4 Cl2 F6 N4 O S'
_chemical_formula_sum            'C12.5 H4 Cl2 F6 N4 O S'
_chemical_formula_weight         443.16
_chemical_name_systematic
;
5,5'-(methylenebis(azanediyl))bis(1-(2,6-dichloro-4-(trifluoromethyl)
phenyl)-4-((trifluoromethyl)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
_atom_sites_solution_primary     dual
_cell_angle_alpha                90.00
_cell_angle_beta                 93.238(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.0584(9)
_cell_length_b                   16.1373(7)
_cell_length_c                   10.6232(5)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.0830
_cell_measurement_theta_min      2.7230
_cell_volume                     3433.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35.
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0757811000
_diffrn_orient_matrix_UB_12      0.0086800000
_diffrn_orient_matrix_UB_13      -0.0290686000
_diffrn_orient_matrix_UB_21      -0.0100160000
_diffrn_orient_matrix_UB_22      0.0138819000
_diffrn_orient_matrix_UB_23      0.1411582000
_diffrn_orient_matrix_UB_31      0.0084819000
_diffrn_orient_matrix_UB_32      0.0940744000
_diffrn_orient_matrix_UB_33      -0.0180980000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.336
_diffrn_reflns_theta_min         3.517
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.257
_exptl_absorpt_correction_T_min  0.58435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Crystallogr. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       0.00098(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0412P)^2^+1.2017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1912
_reflns_number_total             3311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0018_suppl.cif
_cod_data_source_block           exp_7274
_cod_original_formula_sum        'C12.50 H4 Cl2 F6 N4 O S'
_cod_database_code               8105813
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.678
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 F4, F6, C13, F4A, F6A, F5, F5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F5A)=Sof(F4A)=Sof(F6A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Fixed Sof: H6A(0.5) H6B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C11(H11)
;