#------------------------------------------------------------------------------
#$Date: 2022-11-14 10:50:16 +0200 (Mon, 14 Nov 2022) $
#$Revision: 279247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106073.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106073
loop_
_publ_author_name
'Li, Xin-Hong'
'Qin, Zhao-Xian'
'Cao, Sheng-Li'
_publ_section_title
;
 Crystal structure of methyl
 (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate,
 C10H8FN3OS2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              131
_journal_page_last               132
_journal_paper_doi               10.1515/ncrs-2017-0218
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C10 H8 F N3 O S2'
_chemical_formula_weight         269.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.396(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2909(2)
_cell_length_b                   7.4103(2)
_cell_length_c                   24.7079(6)
_cell_measurement_reflns_used    2316
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.10
_cell_measurement_theta_min      5.76
_cell_volume                     1142.24(6)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL[8] DIAMOND[9]'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4237
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.679
_diffrn_reflns_theta_min         1.662
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0375
_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)+(0.0492P)²+0.0721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2055
_reflns_number_total             2316
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0218_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106073
_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   0.98
_shelx_estimated_absorpt_t_max   0.97
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.51079(8) 0.55752(8) 0.73725(2) 0.03156(16) Uani 1 1 d . . . . .
S1 S 0.87398(7) 0.74803(7) 0.69049(2) 0.02957(16) Uani 1 1 d . . . . .
F1 F 0.9211(2) 0.9622(2) 0.41251(5) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.1503(2) 0.5651(2) 0.56565(6) 0.0299(3) Uani 1 1 d . . . . .
N1 N 0.2120(2) 0.6427(2) 0.47797(6) 0.0281(4) Uani 1 1 d . . . . .
H1A H 0.0938 0.6056 0.4601 0.034 Uiso 1 1 calc R U . . .
N3 N 0.5034(2) 0.6614(2) 0.63661(6) 0.0266(4) Uani 1 1 d . . . . .
H3A H 0.3726 0.6249 0.6319 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2607(3) 0.6316(3) 0.53294(7) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.5934(2) 0.7257(2) 0.59387(6) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.9652(3) 0.7363(3) 0.76235(8) 0.0332(5) Uani 1 1 d . . . . .
H10A H 1.1074 0.7850 0.7694 0.050 Uiso 1 1 calc R U . . .
H10B H 0.9663 0.6128 0.7741 0.050 Uiso 1 1 calc R U . . .
H10C H 0.8705 0.8049 0.7820 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4801(3) 0.7138(3) 0.54628(8) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.7327(3) 0.8517(3) 0.48182(8) 0.0276(4) Uani 1 1 d . . . . .
H2B H 0.8443 0.8843 0.5084 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3805(3) 0.7228(3) 0.45399(8) 0.0256(4) Uani 1 1 d . . . . .
C5 C 0.3935(3) 0.7574(3) 0.39960(8) 0.0308(4) Uani 1 1 d . . . . .
H5A H 0.2813 0.7278 0.3728 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5788(3) 0.8378(3) 0.38616(8) 0.0328(4) Uani 1 1 d . . . . .
H6A H 0.5937 0.8616 0.3499 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6183(3) 0.6539(3) 0.68739(7) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.5478(3) 0.7692(2) 0.49493(8) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.7417(3) 0.8824(3) 0.42727(8) 0.0298(4) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 S1 C10 101.49(9) . .
C8 N1 C4 111.20(15) . .
C8 N1 H1A 124.4 . .
C4 N1 H1A 124.4 . .
N2 N3 C9 120.53(16) . .
N2 N3 H3A 119.7 . .
C9 N3 H3A 119.7 . .
O1 C8 N1 127.37(17) . .
O1 C8 C7 126.52(17) . .
N1 C8 C7 106.10(16) . .
C7 N2 N3 116.67(16) . .
S1 C10 H10A 109.5 . .
S1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
S1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C7 C3 125.82(18) . .
N2 C7 C8 127.39(18) . .
C3 C7 C8 106.71(15) . .
C1 C2 C3 116.29(18) . .
C1 C2 H2B 121.9 . .
C3 C2 H2B 121.9 . .
C5 C4 C3 121.46(19) . .
C5 C4 N1 129.00(18) . .
C3 C4 N1 109.53(17) . .
C4 C5 C6 118.02(18) . .
C4 C5 H5A 121.0 . .
C6 C5 H5A 121.0 . .
C1 C6 C5 119.45(18) . .
C1 C6 H6A 120.3 . .
C5 C6 H6A 120.3 . .
N3 C9 S2 119.08(14) . .
N3 C9 S1 113.56(14) . .
S2 C9 S1 127.35(11) . .
C2 C3 C4 120.81(18) . .
C2 C3 C7 132.74(17) . .
C4 C3 C7 106.46(16) . .
F1 C1 C2 118.27(18) . .
F1 C1 C6 117.77(18) . .
C2 C1 C6 123.96(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S2 C9 1.6433(19) .
S1 C9 1.7456(19) .
S1 C10 1.796(2) .
F1 C1 1.365(2) .
O1 C8 1.234(2) .
N1 C8 1.356(2) .
N1 C4 1.410(2) .
N1 H1A 0.8600 .
N3 N2 1.348(2) .
N3 C9 1.366(2) .
N3 H3A 0.8600 .
C8 C7 1.506(2) .
N2 C7 1.297(2) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C7 C3 1.449(3) .
C2 C1 1.375(3) .
C2 C3 1.388(3) .
C2 H2B 0.9300 .
C4 C5 1.381(3) .
C4 C3 1.406(2) .
C5 C6 1.387(3) .
C5 H5A 0.9300 .
C6 C1 1.387(3) .
C6 H6A 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 C8 O1 -178.20(19) . . . .
C4 N1 C8 C7 0.7(2) . . . .
C9 N3 N2 C7 174.17(18) . . . .
N3 N2 C7 C3 -178.07(17) . . . .
N3 N2 C7 C8 -1.7(3) . . . .
O1 C8 C7 N2 1.6(3) . . . .
N1 C8 C7 N2 -177.21(19) . . . .
O1 C8 C7 C3 178.56(19) . . . .
N1 C8 C7 C3 -0.3(2) . . . .
C8 N1 C4 C5 179.8(2) . . . .
C8 N1 C4 C3 -0.8(2) . . . .
C3 C4 C5 C6 0.9(3) . . . .
N1 C4 C5 C6 -179.77(19) . . . .
C4 C5 C6 C1 -0.8(3) . . . .
N2 N3 C9 S2 -174.36(14) . . . .
N2 N3 C9 S1 4.3(2) . . . .
C10 S1 C9 N3 174.39(15) . . . .
C10 S1 C9 S2 -7.13(16) . . . .
C1 C2 C3 C4 -0.6(3) . . . .
C1 C2 C3 C7 179.2(2) . . . .
C5 C4 C3 C2 -0.1(3) . . . .
N1 C4 C3 C2 -179.60(17) . . . .
C5 C4 C3 C7 -179.99(18) . . . .
N1 C4 C3 C7 0.5(2) . . . .
N2 C7 C3 C2 -3.0(4) . . . .
C8 C7 C3 C2 -180.0(2) . . . .
N2 C7 C3 C4 176.82(19) . . . .
C8 C7 C3 C4 -0.1(2) . . . .
C3 C2 C1 F1 -179.63(17) . . . .
C3 C2 C1 C6 0.6(3) . . . .
C5 C6 C1 F1 -179.64(19) . . . .
C5 C6 C1 C2 0.1(3) . . . .
