#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239163.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_2239163
loop_
_publ_author_name
'Bittencourt, Viviane Conceição Duarte de'
'de Vicenti, Juliano Rosa'
'Velasques, Jecika Maciel'
'Zambiazi, Priscilla Jussiane'
'Gervini, Vanessa Carratu'
_publ_section_title
;
 2-(5-Chloro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o64
_journal_page_last               o65
_journal_paper_doi               10.1107/S1600536813033369
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C9 H7 Cl N4 O S'
_chemical_formula_moiety         'C9 H7 Cl N4 O S'
_chemical_formula_sum            'C9 H7 Cl N4 O S'
_chemical_formula_weight         254.70
_chemical_name_common
;
1-(5-Chloro-2-oxoindolin-3-ylidene)thiosemicarbazone
;
_chemical_name_systematic
;
2-(5-Chloro-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                 96.53(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.260(5)
_cell_length_b                   15.396(10)
_cell_length_c                   13.215(9)
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.04
_cell_volume                     1063.2(14)
_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      173
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Graphite monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6939
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          1.27
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0594P)²+1.1793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                2374
_reflns_number_total             2540
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lr2119sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1063.4(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239163
_cod_database_fobs_code          2239163
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
Cl Cl1 1.30216(7) 0.60089(2) -0.07671(3) 0.02850(11) Uani d . 1 1
S S1 0.02044(6) 0.54702(2) 0.36977(3) 0.01934(10) Uani d . 1 1
O O1 0.35742(18) 0.80256(6) 0.24115(7) 0.0187(2) Uani d . 1 1
N N1 0.3377(3) 0.47463(8) 0.24996(11) 0.0285(3) Uani d . 1 1
N N2 0.3459(2) 0.62260(7) 0.25988(8) 0.0162(2) Uani d . 1 1
N N3 0.5262(2) 0.62044(7) 0.19443(8) 0.0159(2) Uani d . 1 1
N N4 0.6662(2) 0.83859(7) 0.13477(8) 0.0166(2) Uani d . 1 1
C C1 0.2444(2) 0.54529(8) 0.28857(10) 0.0163(2) Uani d . 1 1
C C2 0.6101(2) 0.69327(8) 0.16351(9) 0.0148(2) Uani d . 1 1
C C3 0.8029(2) 0.70274(8) 0.09346(9) 0.0152(2) Uani d . 1 1
C C4 0.9460(2) 0.64250(8) 0.04630(10) 0.0173(2) Uani d . 1 1
H H4 0.9271 0.5819 0.0565 0.021 Uiso calc R 1 1
C C5 1.1187(2) 0.67488(9) -0.01663(10) 0.0189(3) Uani d . 1 1
C C6 1.1518(2) 0.76349(9) -0.03214(10) 0.0192(3) Uani d . 1 1
H H6 1.2728 0.7829 -0.0753 0.023 Uiso calc R 1 1
C C8 0.8326(2) 0.79228(8) 0.07785(9) 0.0152(2) Uani d . 1 1
C C9 0.5256(2) 0.78350(8) 0.18693(10) 0.0156(2) Uani d . 1 1
C C7 1.0070(3) 0.82389(9) 0.01575(10) 0.0180(3) Uani d . 1 1
H H7 1.0274 0.8845 0.0061 0.022 Uiso calc R 1 1
H H21 0.291(3) 0.6714(12) 0.2814(13) 0.017(4) Uiso d . 1 1
H H41 0.637(4) 0.8958(15) 0.1304(16) 0.035(5) Uiso d . 1 1
H H11 0.276(4) 0.4232(15) 0.2616(16) 0.033(5) Uiso d . 1 1
H H12 0.459(5) 0.4835(18) 0.210(2) 0.054(7) Uiso d . 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'
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
C1 N1 H11 121.0(14)
C1 N1 H12 115.4(18)
H11 N1 H12 124(2)
N3 N2 C1 118.47(11)
N3 N2 H21 121.0(12)
C1 N2 H21 120.5(12)
C2 N3 N2 118.11(11)
C9 N4 C8 111.12(11)
C9 N4 H41 123.0(14)
C8 N4 H41 125.2(14)
N1 C1 N2 115.72(13)
N1 C1 S1 125.31(10)
N2 C1 S1 118.97(10)
N3 C2 C3 125.26(11)
N3 C2 C9 128.28(12)
C3 C2 C9 106.41(10)
C4 C3 C8 121.02(12)
C4 C3 C2 132.21(12)
C8 C3 C2 106.77(11)
C3 C4 C5 116.98(13)
C3 C4 H4 121.5
C5 C4 H4 121.5
C4 C5 C6 122.65(12)
C4 C5 Cl1 118.11(11)
C6 C5 Cl1 119.23(11)
C5 C6 C7 120.06(12)
C5 C6 H6 120.0
C7 C6 H6 120.0
C7 C8 C3 121.54(12)
C7 C8 N4 129.09(12)
C3 C8 N4 109.36(11)
O1 C9 N4 127.66(12)
O1 C9 C2 126.00(11)
N4 C9 C2 106.33(11)
C8 C7 C6 117.75(13)
C8 C7 H7 121.1
C6 C7 H7 121.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7417(16)
S1 C1 1.6816(17)
O1 C9 1.2354(18)
N1 C1 1.3196(18)
N1 H11 0.88(2)
N1 H12 0.88(3)
N2 N3 1.3548(17)
N2 C1 1.3753(17)
N2 H21 0.865(18)
N3 C2 1.2886(18)
N4 C9 1.3629(17)
N4 C8 1.4108(17)
N4 H41 0.90(2)
C2 C3 1.4561(19)
C2 C9 1.5015(19)
C3 C4 1.3863(18)
C3 C8 1.4052(19)
C4 C5 1.3919(19)
C4 H4 0.9500
C5 C6 1.393(2)
C6 C7 1.398(2)
C6 H6 0.9500
C8 C7 1.3869(19)
C7 H7 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
N2 H21 O1 . 0.865(18) 2.127(18) 2.783(2) 132.2(15)
N4 H41 S1 2 0.90(2) 2.47(2) 3.354(2) 169.5(19)
N1 H11 O1 2_545 0.88(2) 1.98(2) 2.848(2) 169(2)
N1 H12 N3 . 0.88(3) 2.15(3) 2.594(2) 110(2)
N1 H12 Cl1 3_765 0.88(3) 2.62(3) 3.342(2) 139(2)
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
C1 N2 N3 C2 176.25(12)
N3 N2 C1 N1 1.08(19)
N3 N2 C1 S1 180.00(9)
N2 N3 C2 C3 -179.99(11)
N2 N3 C2 C9 -3.0(2)
N3 C2 C3 C4 -2.3(2)
C9 C2 C3 C4 -179.81(13)
N3 C2 C3 C8 178.32(12)
C9 C2 C3 C8 0.79(14)
C8 C3 C4 C5 -0.01(19)
C2 C3 C4 C5 -179.33(13)
C3 C4 C5 C6 0.6(2)
C3 C4 C5 Cl1 179.81(9)
C4 C5 C6 C7 -0.5(2)
Cl1 C5 C6 C7 -179.75(10)
C4 C3 C8 C7 -0.62(19)
C2 C3 C8 C7 178.86(11)
C4 C3 C8 N4 -179.71(11)
C2 C3 C8 N4 -0.23(14)
C9 N4 C8 C7 -179.50(12)
C9 N4 C8 C3 -0.49(15)
C8 N4 C9 O1 -177.55(12)
C8 N4 C9 C2 0.97(14)
N3 C2 C9 O1 0.0(2)
C3 C2 C9 O1 177.47(12)
N3 C2 C9 N4 -178.51(13)
C3 C2 C9 N4 -1.08(13)
C3 C8 C7 C6 0.66(19)
N4 C8 C7 C6 179.56(12)
C5 C6 C7 C8 -0.11(19)
