#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/05/2230534.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_2230534
loop_
_publ_author_name
'Lo, Kong Mun'
'Ng, Seik Weng'
_publ_section_title
;
 5-Chloro-2-hydroxybenzaldehyde 4-ethylthiosemicarbazone
;
_journal_coeditor_code           XU5210
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1453
_journal_paper_doi               10.1107/S160053681101796X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H12 Cl N3 O S'
_chemical_formula_moiety         'C10 H12 Cl N3 O S'
_chemical_formula_sum            'C10 H12 Cl N3 O S'
_chemical_formula_weight         257.74
_chemical_name_systematic
;
5-Chloro-2-hydroxybenzaldehyde 4-ethylthiosemicarbazone
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 101.6870(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.7956(3)
_cell_length_b                   11.8536(2)
_cell_length_c                   9.41550(10)
_cell_measurement_reflns_used    6011
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.81
_cell_volume                     2382.12(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11204
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  0.8318
_exptl_absorpt_correction_T_min  0.8318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0483P)²+1.7745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                2582
_reflns_number_total             2985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5210.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2230534
_cod_database_fobs_code          2230534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.485785(16) 0.65980(4) 0.51634(4) 0.03990(13) Uani d . 1 1 . .
S S1 0.835591(14) 0.65767(3) -0.01381(3) 0.01821(10) Uani d . 1 1 . .
O O1 0.75861(4) 0.62629(8) 0.57947(10) 0.01950(19) Uani d D 1 1 . .
N N1 0.73919(5) 0.61554(8) 0.29057(11) 0.0159(2) Uani d . 1 1 . .
N N2 0.75536(5) 0.63100(9) 0.15711(11) 0.0167(2) Uani d D 1 1 . .
N N3 0.85219(5) 0.55435(9) 0.24435(11) 0.0169(2) Uani d D 1 1 . .
C C1 0.69537(6) 0.62896(10) 0.56025(13) 0.0160(2) Uani d . 1 1 . .
C C2 0.66935(6) 0.63906(10) 0.68348(14) 0.0189(2) Uani d . 1 1 . .
H H2 0.6959 0.6406 0.7769 0.023 Uiso calc R 1 1 . .
C C3 0.60511(6) 0.64685(11) 0.67054(14) 0.0215(3) Uani d . 1 1 . .
H H3 0.5875 0.6549 0.7544 0.026 Uiso calc R 1 1 . .
C C4 0.56661(6) 0.64280(12) 0.53368(15) 0.0230(3) Uani d . 1 1 . .
C C5 0.59099(6) 0.63056(11) 0.41045(14) 0.0203(3) Uani d . 1 1 . .
H H5 0.5638 0.6262 0.3180 0.024 Uiso calc R 1 1 . .
C C6 0.65605(5) 0.62453(10) 0.42189(13) 0.0160(2) Uani d . 1 1 . .
C C7 0.68017(5) 0.62429(10) 0.28864(13) 0.0166(2) Uani d . 1 1 . .
H H7 0.6517 0.6307 0.1982 0.020 Uiso calc R 1 1 . .
C C8 0.81461(5) 0.61070(10) 0.14031(12) 0.0152(2) Uani d . 1 1 . .
C C9 0.91574(5) 0.51980(11) 0.23606(13) 0.0199(2) Uani d . 1 1 . .
H H9A 0.9414 0.5132 0.3353 0.024 Uiso calc R 1 1 . .
H H9B 0.9350 0.5783 0.1840 0.024 Uiso calc R 1 1 . .
C C10 0.91595(6) 0.40780(12) 0.15821(14) 0.0235(3) Uani d . 1 1 . .
H H10A 0.9591 0.3872 0.1542 0.035 Uiso calc R 1 1 . .
H H10B 0.8911 0.4144 0.0594 0.035 Uiso calc R 1 1 . .
H H10C 0.8977 0.3494 0.2107 0.035 Uiso calc R 1 1 . .
H H1O 0.7673(10) 0.6201(18) 0.4975(14) 0.057(6) Uiso d D 1 1 . .
H H2N 0.7319(6) 0.6770(11) 0.0975(14) 0.017(4) Uiso d D 1 1 . .
H H3N 0.8351(7) 0.5207(13) 0.3075(15) 0.026(4) Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1O . . 107.2(15) ?
C7 N1 N2 . . 114.46(10) ?
C8 N2 N1 . . 120.45(10) ?
C8 N2 H2N . . 119.1(10) ?
N1 N2 H2N . . 116.3(10) ?
C8 N3 C9 . . 123.58(10) ?
C8 N3 H3N . . 117.1(11) ?
C9 N3 H3N . . 117.0(11) ?
O1 C1 C2 . . 117.70(11) ?
O1 C1 C6 . . 122.36(11) ?
C2 C1 C6 . . 119.92(11) ?
C3 C2 C1 . . 120.44(12) ?
C3 C2 H2 . . 119.8 ?
C1 C2 H2 . . 119.8 ?
C2 C3 C4 . . 119.33(12) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C5 C4 C3 . . 121.41(12) ?
C5 C4 Cl1 . . 119.13(10) ?
C3 C4 Cl1 . . 119.40(10) ?
C4 C5 C6 . . 119.81(12) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C5 C6 C1 . . 119.07(11) ?
C5 C6 C7 . . 118.05(11) ?
C1 C6 C7 . . 122.65(11) ?
N1 C7 C6 . . 121.50(11) ?
N1 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
N3 C8 N2 . . 117.72(10) ?
N3 C8 S1 . . 124.30(9) ?
N2 C8 S1 . . 117.97(9) ?
N3 C9 C10 . . 111.51(10) ?
N3 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
N3 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 . 1.7476(13) ?
S1 C8 . 1.7011(12) ?
O1 C1 . 1.3539(14) ?
O1 H1O . 0.835(9) ?
N1 C7 . 1.2870(15) ?
N1 N2 . 1.3842(13) ?
N2 C8 . 1.3541(14) ?
N2 H2N . 0.870(9) ?
N3 C8 . 1.3234(15) ?
N3 C9 . 1.4615(14) ?
N3 H3N . 0.860(9) ?
C1 C2 . 1.3959(17) ?
C1 C6 . 1.4078(17) ?
C2 C3 . 1.3837(17) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3889(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3782(18) ?
C5 C6 . 1.4020(16) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4552(16) ?
C7 H7 . 0.9500 ?
C9 C10 . 1.5169(18) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
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
O1 H1o N1 . 0.840(10) 1.920(10) 2.670(2) 149(2) yes
N2 H2n S1 7_665 0.870(10) 2.480(10) 3.3080(10) 159.0(10) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 N2 C8 . . . . -171.98(11) ?
O1 C1 C2 C3 . . . . 177.38(11) ?
C6 C1 C2 C3 . . . . -1.19(18) ?
C1 C2 C3 C4 . . . . 0.97(19) ?
C2 C3 C4 C5 . . . . 0.4(2) ?
C2 C3 C4 Cl1 . . . . -176.77(10) ?
C3 C4 C5 C6 . . . . -1.5(2) ?
Cl1 C4 C5 C6 . . . . 175.68(10) ?
C4 C5 C6 C1 . . . . 1.21(18) ?
C4 C5 C6 C7 . . . . -173.28(12) ?
O1 C1 C6 C5 . . . . -178.40(11) ?
C2 C1 C6 C5 . . . . 0.09(17) ?
O1 C1 C6 C7 . . . . -4.18(17) ?
C2 C1 C6 C7 . . . . 174.32(12) ?
N2 N1 C7 C6 . . . . -172.18(10) ?
C5 C6 C7 N1 . . . . -177.90(11) ?
C1 C6 C7 N1 . . . . 7.82(18) ?
C9 N3 C8 N2 . . . . 175.63(11) ?
C9 N3 C8 S1 . . . . -3.54(17) ?
N1 N2 C8 N3 . . . . 13.77(17) ?
N1 N2 C8 S1 . . . . -167.01(8) ?
C8 N3 C9 C10 . . . . -85.80(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656744
