#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/75/2227527.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_2227527
loop_
_publ_author_name
'Li, Yu-Feng'
_publ_section_title
;
 1-(2,4-Dichlorobenzylidene)-4-ethylthiosemicarbazide
;
_journal_coeditor_code           HB5632
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2550
_journal_paper_doi               10.1107/S1600536810035671
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H11 Cl2 N3 S'
_chemical_formula_moiety         'C10 H11 Cl2 N3 S'
_chemical_formula_sum            'C10 H11 Cl2 N3 S'
_chemical_formula_weight         276.18
_chemical_name_systematic
;
1-(2,4-Dichlorobenzylidene)-4-ethylthiosemicarbazide
;
_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                 101.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4339(11)
_cell_length_b                   20.526(4)
_cell_length_c                   11.313(2)
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.50
_cell_volume                     1234.4(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1092
_diffrn_reflns_av_sigmaI/netI    0.1147
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10913
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.919
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0600
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1865
_reflns_number_gt                1416
_reflns_number_total             2707
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5632.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227527
_cod_database_fobs_code          2227527
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_disorder_assembly
_atom_site_disorder_group
S S1 -0.1063(2) 0.99987(6) 0.79802(13) 0.0434(4) Uani d . 1 . .
Cl Cl2 0.7303(2) 0.85591(6) 1.34950(13) 0.0499(4) Uani d . 1 . .
Cl Cl1 1.4115(2) 0.70212(6) 1.20880(15) 0.0558(4) Uani d . 1 . .
N N3 0.4756(6) 0.90330(15) 0.9707(4) 0.0355(9) Uani d . 1 . .
N N2 0.2667(7) 0.94274(17) 0.9454(4) 0.0390(9) Uani d . 1 . .
H H2A 0.2030 0.9583 1.0029 0.047 Uiso calc R 1 . .
N N1 0.2795(7) 0.93533(18) 0.7450(4) 0.0410(10) Uani d . 1 . .
H H1A 0.4117 0.9118 0.7681 0.049 Uiso calc R 1 . .
C C5 0.7795(7) 0.84768(18) 1.1156(4) 0.0317(10) Uani d . 1 . .
C C3 0.1623(7) 0.95672(19) 0.8288(4) 0.0324(10) Uani d . 1 . .
C C8 1.1713(8) 0.7596(2) 1.1742(5) 0.0381(11) Uani d . 1 . .
C C9 1.0643(8) 0.78286(19) 1.2644(5) 0.0393(12) Uani d . 1 . .
H H9A 1.1209 0.7695 1.3440 0.047 Uiso calc R 1 . .
C C4 0.5640(8) 0.89200(19) 1.0829(5) 0.0373(11) Uani d . 1 . .
H H4A 0.4932 0.9114 1.1423 0.045 Uiso calc R 1 . .
C C7 1.0936(9) 0.7793(2) 1.0562(5) 0.0418(12) Uani d . 1 . .
H H7A 1.1715 0.7632 0.9964 0.050 Uiso calc R 1 . .
C C10 0.8684(8) 0.82717(19) 1.2342(4) 0.0332(10) Uani d . 1 . .
C C6 0.8994(8) 0.8232(2) 1.0276(5) 0.0384(11) Uani d . 1 . .
H H6A 0.8471 0.8368 0.9480 0.046 Uiso calc R 1 . .
C C2 0.2011(10) 0.9487(3) 0.6169(5) 0.0492(13) Uani d . 1 . .
H H2B 0.2201 0.9949 0.6029 0.059 Uiso calc R 1 . .
H H2C 0.0246 0.9377 0.5906 0.059 Uiso calc R 1 . .
C C1 0.3510(11) 0.9109(3) 0.5440(6) 0.0641(16) Uani d . 1 . .
H H1B 0.2935 0.9209 0.4599 0.096 Uiso calc R 1 . .
H H1C 0.3306 0.8651 0.5567 0.096 Uiso calc R 1 . .
H H1D 0.5255 0.9223 0.5686 0.096 Uiso calc R 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'
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
C4 N3 N2 . . 115.8(4) ?
C3 N2 N3 . . 119.2(4) ?
C3 N2 H2A . . 120.4 ?
N3 N2 H2A . . 120.4 ?
C3 N1 C2 . . 124.7(4) ?
C3 N1 H1A . . 117.7 ?
C2 N1 H1A . . 117.7 ?
C6 C5 C10 . . 117.3(4) ?
C6 C5 C4 . . 120.7(4) ?
C10 C5 C4 . . 121.9(4) ?
N1 C3 N2 . . 117.5(4) ?
N1 C3 S1 . . 123.6(4) ?
N2 C3 S1 . . 118.9(4) ?
C9 C8 C7 . . 122.1(4) ?
C9 C8 Cl1 . . 119.0(4) ?
C7 C8 Cl1 . . 118.8(4) ?
C8 C9 C10 . . 118.0(5) ?
C8 C9 H9A . . 121.0 ?
C10 C9 H9A . . 121.0 ?
N3 C4 C5 . . 118.5(5) ?
N3 C4 H4A . . 120.8 ?
C5 C4 H4A . . 120.8 ?
C6 C7 C8 . . 119.2(5) ?
C6 C7 H7A . . 120.4 ?
C8 C7 H7A . . 120.4 ?
C9 C10 C5 . . 122.1(4) ?
C9 C10 Cl2 . . 117.8(4) ?
C5 C10 Cl2 . . 120.2(3) ?
C7 C6 C5 . . 121.3(5) ?
C7 C6 H6A . . 119.3 ?
C5 C6 H6A . . 119.3 ?
N1 C2 C1 . . 111.9(4) ?
N1 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
N1 C2 H2C . . 109.2 ?
C1 C2 H2C . . 109.2 ?
H2B C2 H2C . . 107.9 ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 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
S1 C3 . 1.681(4) ?
Cl2 C10 . 1.738(5) ?
Cl1 C8 . 1.743(4) ?
N3 C4 . 1.282(6) ?
N3 N2 . 1.375(5) ?
N2 C3 . 1.354(6) ?
N2 H2A . 0.8600 ?
N1 C3 . 1.322(6) ?
N1 C2 . 1.449(7) ?
N1 H1A . 0.8600 ?
C5 C6 . 1.392(7) ?
C5 C10 . 1.393(6) ?
C5 C4 . 1.468(6) ?
C8 C9 . 1.362(7) ?
C8 C7 . 1.376(7) ?
C9 C10 . 1.388(6) ?
C9 H9A . 0.9300 ?
C4 H4A . 0.9300 ?
C7 C6 . 1.373(6) ?
C7 H7A . 0.9300 ?
C6 H6A . 0.9300 ?
C2 C1 . 1.491(7) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
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 H2A S1 3_577 0.86 2.56 3.409(5) 168
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 6040072
