#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/38/2233847.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_2233847
loop_
_publ_author_name
'Pervez, Humayun'
'Manzoor, Nazia'
'Yaqub, Muhammad'
'Tahir, M. Nawaz'
_publ_section_title
;
 (Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide
;
_journal_coeditor_code           HB6630
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o670
_journal_paper_doi               10.1107/S1600536812005053
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H10 F N5 O3 S'
_chemical_formula_moiety         'C15 H10 F N5 O3 S'
_chemical_formula_sum            'C15 H10 F N5 O3 S'
_chemical_formula_weight         359.34
_chemical_name_systematic
;
(Z)-4-(3-Fluorophenyl)-1-(5-nitro-2-oxoindolin-3-
ylidene)thiosemicarbazide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.2485(5)
_cell_length_b                   8.8043(2)
_cell_length_c                   18.6913(5)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.18
_cell_volume                     3003.04(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.50
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            53231
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.280
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0373
_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)+(0.0450P)²+1.1466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                3101
_reflns_number_total             3728
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6630.cif
_cod_data_source_block           I
_cod_database_code               2233847
_cod_database_fobs_code          2233847
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
S S1 0.23197(2) 0.67952(5) -0.04002(2) 0.04680(10) Uani 1.000 -16
F F1 0.41277(8) 1.02225(17) -0.14952(9) 0.1015(6) Uani 1.000 -16
O O1 0.14958(6) 0.37037(13) 0.13575(6) 0.0491(4) Uani 1.000 -16
O O2 0.50290(8) 0.02530(18) 0.34644(8) 0.0759(5) Uani 1.000 -16
O O3 0.53143(7) 0.1873(2) 0.26498(9) 0.0811(6) Uani 1.000 -16
N N1 0.36565(7) 0.62197(15) 0.01839(7) 0.0421(4) Uani 1.000 -16
N N2 0.26518(6) 0.51166(14) 0.06902(6) 0.0388(3) Uani 1.000 -16
N N3 0.31021(6) 0.43761(13) 0.11392(6) 0.0361(3) Uani 1.000 -16
N N4 0.19541(6) 0.21196(13) 0.22400(7) 0.0379(3) Uani 1.000 -16
N N5 0.48641(8) 0.11444(18) 0.29912(8) 0.0531(4) Uani 1.000 -16
C C1 0.41226(8) 0.72152(17) -0.01991(8) 0.0400(4) Uani 1.000 -16
C C2 0.38746(9) 0.8269(2) -0.06921(10) 0.0535(5) Uani 1.000 -16
C C3 0.43845(11) 0.9188(2) -0.10154(11) 0.0600(6) Uani 1.000 -16
C C4 0.51147(11) 0.9129(2) -0.08870(11) 0.0608(6) Uani 1.000 -16
C C5 0.53538(10) 0.8073(2) -0.03948(10) 0.0599(6) Uani 1.000 -16
C C6 0.48660(9) 0.7113(2) -0.00505(9) 0.0493(5) Uani 1.000 -16
C C7 0.29264(8) 0.60528(15) 0.01605(7) 0.0363(4) Uani 1.000 -16
C C8 0.28008(7) 0.34713(15) 0.15985(7) 0.0329(3) Uani 1.000 -16
C C9 0.20008(7) 0.31556(15) 0.16965(8) 0.0358(4) Uani 1.000 -16
C C10 0.26468(7) 0.17306(15) 0.24998(7) 0.0336(3) Uani 1.000 -16
C C11 0.31818(7) 0.25505(15) 0.21213(7) 0.0324(3) Uani 1.000 -16
C C12 0.39169(7) 0.23766(16) 0.22778(7) 0.0365(4) Uani 1.000 -16
C C13 0.40880(8) 0.13552(17) 0.28157(8) 0.0402(4) Uani 1.000 -16
C C14 0.35672(9) 0.05368(18) 0.31899(8) 0.0445(5) Uani 1.000 -16
C C15 0.28301(8) 0.07168(17) 0.30351(8) 0.0412(4) Uani 1.000 -16
H H1 0.38771 0.56263 0.04792 0.0505 Uiso 1.000 -16
H H2 0.33789 0.83526 -0.08008 0.0643 Uiso 1.000 -16
H H2A 0.21856 0.50064 0.07329 0.0466 Uiso 1.000 -16
H H4 0.54402 0.97735 -0.11205 0.0730 Uiso 1.000 -16
H H4A 0.15495 0.17542 0.24013 0.0455 Uiso 1.000 -16
H H5 0.58513 0.80035 -0.02920 0.0719 Uiso 1.000 -16
H H6 0.50361 0.64038 0.02787 0.0592 Uiso 1.000 -16
H H12 0.42774 0.29165 0.20349 0.0438 Uiso 1.000 -16
H H14 0.37122 -0.01361 0.35464 0.0534 Uiso 1.000 -16
H H15 0.24724 0.01765 0.32818 0.0494 Uiso 1.000 -16
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'
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_publ_flag
C1 N1 C7 130.41(13) no
N3 N2 C7 121.01(11) no
N2 N3 C8 116.96(11) no
C9 N4 C10 111.43(11) no
O2 N5 O3 123.39(16) no
O2 N5 C13 118.82(14) no
O3 N5 C13 117.79(14) no
C1 N1 H1 115.00 no
C7 N1 H1 115.00 no
N3 N2 H2A 119.00 no
C7 N2 H2A 119.00 no
C9 N4 H4A 124.00 no
C10 N4 H4A 124.00 no
N1 C1 C2 123.74(14) no
N1 C1 C6 116.49(14) no
C2 C1 C6 119.77(14) no
C1 C2 C3 117.81(16) no
F1 C3 C4 118.74(17) no
C2 C3 C4 124.46(18) no
F1 C3 C2 116.80(17) no
C3 C4 C5 117.08(18) no
C4 C5 C6 121.18(17) no
C1 C6 C5 119.70(16) no
S1 C7 N2 116.46(11) no
S1 C7 N1 129.83(11) no
N1 C7 N2 113.71(12) no
C9 C8 C11 106.36(11) no
N3 C8 C9 127.58(12) no
N3 C8 C11 126.06(12) no
O1 C9 C8 126.90(13) no
N4 C9 C8 105.98(11) no
O1 C9 N4 127.11(12) no
C11 C10 C15 121.88(12) no
N4 C10 C11 109.13(11) no
N4 C10 C15 128.99(12) no
C8 C11 C12 132.17(12) no
C8 C11 C10 107.09(11) no
C10 C11 C12 120.74(12) no
C11 C12 C13 116.41(12) no
N5 C13 C12 117.56(13) no
N5 C13 C14 119.02(14) no
C12 C13 C14 123.42(14) no
C13 C14 C15 120.15(14) no
C10 C15 C14 117.40(13) no
C1 C2 H2 121.00 no
C3 C2 H2 121.00 no
C3 C4 H4 121.00 no
C5 C4 H4 121.00 no
C4 C5 H5 119.00 no
C6 C5 H5 119.00 no
C1 C6 H6 120.00 no
C5 C6 H6 120.00 no
C11 C12 H12 122.00 no
C13 C12 H12 122.00 no
C13 C14 H14 120.00 no
C15 C14 H14 120.00 no
C10 C15 H15 121.00 no
C14 C15 H15 121.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 1.6587(14) no
F1 C3 1.361(2) no
O1 C9 1.2180(17) no
O2 N5 1.220(2) no
O3 N5 1.222(2) no
N1 C1 1.416(2) no
N1 C7 1.3411(19) no
N2 N3 1.3434(16) no
N2 C7 1.3823(18) no
N3 C8 1.2938(17) no
N4 C9 1.3679(19) no
N4 C10 1.3968(17) no
N5 C13 1.466(2) no
N1 H1 0.8600 no
N2 H2A 0.8600 no
N4 H4A 0.8600 no
C1 C6 1.388(2) no
C1 C2 1.384(2) no
C2 C3 1.373(3) no
C3 C4 1.355(3) no
C4 C5 1.379(3) no
C5 C6 1.386(2) no
C8 C9 1.4974(18) no
C8 C11 1.4476(18) no
C10 C15 1.382(2) no
C10 C11 1.4053(18) no
C11 C12 1.3815(18) no
C12 C13 1.385(2) no
C13 C14 1.383(2) no
C14 C15 1.385(2) no
C2 H2 0.9300 no
C4 H4 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C12 H12 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 no
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
_geom_hbond_publ_flag
N1 H1 N3 . 0.86 2.18 2.6166(17) 112 yes
N2 H2A O1 . 0.86 2.06 2.7483(16) 136 yes
N4 H4A O3 6_455 0.86 2.26 3.0073(17) 146 yes
C2 H2 S1 . 0.93 2.49 3.1674(17) 130 yes
C4 H4 O1 3_565 0.93 2.39 3.281(2) 161 yes
C6 H6 O2 4_655 0.93 2.56 3.392(2) 149 yes
C12 H12 O2 4_655 0.93 2.59 3.470(2) 158 yes
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_publ_flag
C7 N1 C1 C2 0.8(3) no
C7 N1 C1 C6 179.82(15) no
C1 N1 C7 S1 8.9(2) no
C1 N1 C7 N2 -170.96(14) no
C7 N2 N3 C8 -177.01(12) no
N3 N2 C7 S1 175.28(10) no
N3 N2 C7 N1 -4.80(18) no
N2 N3 C8 C9 -0.6(2) no
N2 N3 C8 C11 179.00(12) no
C10 N4 C9 O1 179.28(14) no
C10 N4 C9 C8 -0.30(15) no
C9 N4 C10 C11 0.67(16) no
C9 N4 C10 C15 -179.04(14) no
O2 N5 C13 C12 179.84(15) no
O2 N5 C13 C14 -0.1(2) no
O3 N5 C13 C12 -0.5(2) no
O3 N5 C13 C14 179.53(16) no
N1 C1 C2 C3 178.66(16) no
C6 C1 C2 C3 -0.3(3) no
N1 C1 C6 C5 -178.74(15) no
C2 C1 C6 C5 0.3(2) no
C1 C2 C3 F1 -179.61(16) no
C1 C2 C3 C4 0.3(3) no
F1 C3 C4 C5 179.64(17) no
C2 C3 C4 C5 -0.3(3) no
C3 C4 C5 C6 0.3(3) no
C4 C5 C6 C1 -0.3(3) no
N3 C8 C9 O1 -0.1(2) no
N3 C8 C9 N4 179.51(13) no
C11 C8 C9 O1 -179.74(14) no
C11 C8 C9 N4 -0.17(15) no
N3 C8 C11 C10 -179.13(13) no
N3 C8 C11 C12 0.3(2) no
C9 C8 C11 C10 0.57(14) no
C9 C8 C11 C12 179.97(16) no
N4 C10 C11 C8 -0.76(15) no
N4 C10 C11 C12 179.74(12) no
C15 C10 C11 C8 178.98(13) no
C15 C10 C11 C12 -0.5(2) no
N4 C10 C15 C14 179.89(14) no
C11 C10 C15 C14 0.2(2) no
C8 C11 C12 C13 -178.85(14) no
C10 C11 C12 C13 0.5(2) no
C11 C12 C13 N5 179.80(13) no
C11 C12 C13 C14 -0.2(2) no
N5 C13 C14 C15 179.91(14) no
C12 C13 C14 C15 -0.1(2) no
C13 C14 C15 C10 0.1(2) no
