#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240685.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_2240685
loop_
_publ_author_name
'Bittencourt, Viviane C. D.'
'Almeida, Vitor Y. G.'
'Back, Davi F.'
'Gervini, Vanessa C.'
'de Oliveira, Adriano Bof'
_publ_section_title
;
 Crystal structure of
 (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o383
_journal_page_last               o384
_journal_paper_doi               10.1107/S2056989015008609
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C9 H7 F N4 O1 S1'
_chemical_formula_moiety         'C9 H7 F N4 O1 S1'
_chemical_formula_sum            'C9 H7 F N4 O S'
_chemical_formula_weight         238.25
_chemical_name_common            5-Fluoroisatin-thiosemicarbazone
_chemical_name_systematic
;
(Z)-2-(5-Fluoro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.921(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.71510(10)
_cell_length_b                   15.4517(4)
_cell_length_c                   13.9645(4)
_cell_measurement_reflns_used    1744
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.348
_cell_measurement_theta_min      2.636
_cell_volume                     1015.02(4)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Kappa APEXII'
_diffrn_measurement_method       '0.5 ° ω & φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12531
_diffrn_reflns_theta_full        27.16
_diffrn_reflns_theta_max         27.16
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.1779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1390
_reflns_number_total             2239
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lr2136sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C9 H7 F N4 O1 S1'
_cod_database_code               2240685
_cod_database_fobs_code          2240685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.02917(16) 0.03364(5) 0.86791(6) 0.0558(3) Uani d . 1 1
O O1 0.3669(4) 0.28879(12) 0.73620(14) 0.0506(5) Uani d . 1 1
F F1 1.2874(4) 0.11434(14) 0.40106(15) 0.0840(7) Uani d . 1 1
N N3 0.3467(4) 0.10914(14) 0.74614(16) 0.0452(6) Uani d . 1 1
H H3 0.2958 0.1572 0.7708 0.054 Uiso calc R 1 1
N N1 0.6921(4) 0.32661(14) 0.62633(16) 0.0472(6) Uani d . 1 1
H H1 0.6864 0.3820 0.6319 0.057 Uiso calc R 1 1
N N2 0.5310(4) 0.10861(14) 0.67623(16) 0.0433(5) Uani d . 1 1
N N4 0.3217(5) -0.03703(14) 0.73181(19) 0.0587(7) Uani d . 1 1
H H4A 0.4327 -0.0322 0.6857 0.070 Uiso calc R 1 1
H H4B 0.2628 -0.0872 0.7481 0.070 Uiso calc R 1 1
C C1 0.8212(5) 0.19327(16) 0.57361(19) 0.0411(6) Uani d . 1 1
C C8 0.6233(5) 0.18194(16) 0.64722(19) 0.0402(6) Uani d . 1 1
C C7 0.5406(5) 0.27122(16) 0.67762(19) 0.0413(6) Uani d . 1 1
C C6 0.8603(5) 0.28250(17) 0.56272(19) 0.0412(6) Uani d . 1 1
C C5 1.0436(6) 0.31552(19) 0.4996(2) 0.0502(7) Uani d . 1 1
H H5 1.0706 0.3748 0.4936 0.060 Uiso calc R 1 1
C C3 1.1423(6) 0.1702(2) 0.4555(2) 0.0549(8) Uani d . 1 1
C C2 0.9634(5) 0.13570(19) 0.5189(2) 0.0507(7) Uani d . 1 1
H H2 0.9393 0.0762 0.5246 0.061 Uiso calc R 1 1
C C9 0.2420(5) 0.03249(16) 0.7774(2) 0.0431(6) Uani d . 1 1
C C4 1.1869(6) 0.2569(2) 0.4450(2) 0.0553(8) Uani d . 1 1
H H4 1.3129 0.2766 0.4015 0.066 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N3 C9 119.3(2)
N2 N3 H3 120.3
C9 N3 H3 120.3
C7 N1 C6 111.7(2)
C7 N1 H1 124.2
C6 N1 H1 124.2
C8 N2 N3 118.0(2)
C9 N4 H4A 120.0
C9 N4 H4B 120.0
H4A N4 H4B 120.0
C2 C1 C6 120.2(2)
C2 C1 C8 132.8(2)
C6 C1 C8 107.0(2)
N2 C8 C1 125.3(2)
N2 C8 C7 128.2(2)
C1 C8 C7 106.4(2)
O1 C7 N1 127.9(2)
O1 C7 C8 126.1(2)
N1 C7 C8 106.0(2)
C5 C6 C1 121.9(2)
C5 C6 N1 129.2(3)
C1 C6 N1 108.9(2)
C6 C5 C4 117.4(3)
C6 C5 H5 121.3
C4 C5 H5 121.3
F1 C3 C4 118.3(3)
F1 C3 C2 117.9(3)
C4 C3 C2 123.8(3)
C3 C2 C1 116.8(3)
C3 C2 H2 121.6
C1 C2 H2 121.6
N4 C9 N3 115.6(2)
N4 C9 S1 125.6(2)
N3 C9 S1 118.83(19)
C3 C4 C5 119.8(3)
C3 C4 H4 120.1
C5 C4 H4 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C9 . 1.667(3)
O1 C7 . 1.227(3)
F1 C3 . 1.365(3)
N3 N2 . 1.351(3)
N3 C9 . 1.366(3)
N3 H3 . 0.8600
N1 C7 . 1.351(3)
N1 C6 . 1.407(3)
N1 H1 . 0.8600
N2 C8 . 1.289(3)
N4 C9 . 1.316(3)
N4 H4A . 0.8600
N4 H4B . 0.8600
C1 C2 . 1.377(4)
C1 C6 . 1.401(4)
C1 C8 . 1.446(3)
C8 C7 . 1.503(3)
C7 O1 1 1.227(3)
C6 C5 . 1.374(3)
C5 C4 . 1.388(4)
C5 H5 . 0.9300
C3 C4 . 1.365(4)
C3 C2 . 1.371(4)
C2 H2 . 0.9300
C4 H4 . 0.9300
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 H3 O1 1 0.86 2.12 2.781(3) 133.2
N1 H1 S1 2_556 0.86 2.55 3.367(2) 158.1
N4 H4A F1 3_756 0.86 2.24 2.956(3) 140.0
N4 H4B O1 2_546 0.86 2.03 2.879(3) 170.5
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
C9 N3 N2 C8 179.0(2)
N3 N2 C8 C1 179.8(2)
N3 N2 C8 C7 -3.6(4)
C2 C1 C8 N2 -1.7(5)
C6 C1 C8 N2 178.8(3)
C2 C1 C8 C7 -178.9(3)
C6 C1 C8 C7 1.5(3)
C6 N1 C7 O1 -177.1(3)
C6 N1 C7 C8 1.9(3)
N2 C8 C7 O1 -0.2(5)
C1 C8 C7 O1 176.9(3)
N2 C8 C7 N1 -179.2(3)
C1 C8 C7 N1 -2.1(3)
C2 C1 C6 C5 -1.4(4)
C8 C1 C6 C5 178.2(2)
C2 C1 C6 N1 179.9(2)
C8 C1 C6 N1 -0.5(3)
C7 N1 C6 C5 -179.5(3)
C7 N1 C6 C1 -1.0(3)
C1 C6 C5 C4 1.1(4)
N1 C6 C5 C4 179.5(3)
F1 C3 C2 C1 179.4(3)
C4 C3 C2 C1 0.6(5)
C6 C1 C2 C3 0.5(4)
C8 C1 C2 C3 -178.9(3)
N2 N3 C9 N4 -3.3(4)
N2 N3 C9 S1 176.57(19)
F1 C3 C4 C5 -179.8(3)
C2 C3 C4 C5 -0.9(5)
C6 C5 C4 C3 0.0(4)
