#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227929.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_2227929
loop_
_publ_author_name
'Tarafder, M. T. H.'
'Khan, Sultana Shakila'
'Islam, M. A. A. A. A.'
'Lorenzi, Lea'
'Zangrando, Ennio'
_publ_section_title
;
 Methyl 3-[(E,E)-3-phenylprop-2-enylidene]dithiocarbazate
;
_journal_coeditor_code           PV2336
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2851
_journal_paper_doi               10.1107/S1600536810041115
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H12 N2 S2'
_chemical_formula_moiety         'C11 H12 N2 S2'
_chemical_formula_sum            'C11 H12 N2 S2'
_chemical_formula_weight         236.35
_chemical_name_systematic
;
Methyl 3-[(E,E)-3-phenylprop-2-enylidene]dithiocarbazate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.697(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.408(2)
_cell_length_b                   5.4950(9)
_cell_length_c                   20.988(2)
_cell_measurement_reflns_used    275
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.69
_cell_measurement_theta_min      3.62
_cell_volume                     1179.5(3)
_computing_cell_refinement       'Denzo (Otwinowski & Minor, 1997)'
_computing_data_collection       'XPRESS (MacScience, 2002)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.95
_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type
'Enraf--Nonius DIP1030 image-plate  diffractometer'
_diffrn_measurement_method       'φ-scans with narrow frames'
_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  0.037
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6316
_diffrn_reflns_theta_full        25.3
_diffrn_reflns_theta_max         25.3
_diffrn_reflns_theta_min         3.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0384
_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)+(0.0721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1569
_reflns_number_total             2048
_reflns_threshold_expression     'I > 2.0σ(I)'
_cod_data_source_file            pv2336.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227929
_cod_database_fobs_code          2227929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 1.15322(6) 0.68232(10) 0.57196(3) 0.0759(2) Uani d . 1 . .
S S2 1.08034(6) 0.51686(10) 0.69852(3) 0.0734(2) Uani d . 1 . .
N N1 0.99960(18) 0.3187(3) 0.58644(8) 0.0682(5) Uani d . 1 . .
H H1 0.9962 0.2915 0.5458 0.082 Uiso calc R 1 . .
N N2 0.92717(19) 0.1751(3) 0.62061(9) 0.0680(5) Uani d . 1 . .
C C1 1.1813(3) 0.7789(4) 0.72034(11) 0.0791(6) Uani d . 1 . .
H H1A 1.2653 0.7525 0.7089 0.119 Uiso calc R 1 . .
H H1B 1.1918 0.8059 0.7662 0.119 Uiso calc R 1 . .
H H1C 1.1407 0.9187 0.6976 0.119 Uiso calc R 1 . .
C C2 1.0751(2) 0.4996(3) 0.61523(10) 0.0625(5) Uani d . 1 . .
C C3 0.8633(2) 0.0018(3) 0.58766(11) 0.0656(5) Uani d . 1 . .
H H3 0.8723 -0.0225 0.5449 0.079 Uiso calc R 1 . .
C C4 0.7788(2) -0.1538(3) 0.61562(10) 0.0670(5) Uani d . 1 . .
H H4 0.7718 -0.1294 0.6587 0.080 Uiso calc R 1 . .
C C5 0.7095(2) -0.3328(3) 0.58259(10) 0.0653(5) Uani d . 1 . .
H H5 0.7240 -0.3613 0.5408 0.078 Uiso calc R 1 . .
C C6 0.6139(2) -0.4880(3) 0.60503(10) 0.0634(5) Uani d . 1 . .
C C7 0.5705(3) -0.4487(4) 0.66304(12) 0.0750(6) Uani d . 1 . .
H H7 0.6053 -0.3208 0.6898 0.090 Uiso calc R 1 . .
C C8 0.4770(3) -0.5962(5) 0.68147(14) 0.0898(7) Uani d . 1 . .
H H8 0.4487 -0.5659 0.7202 0.108 Uiso calc R 1 . .
C C9 0.4250(3) -0.7874(5) 0.64316(17) 0.0963(9) Uani d . 1 . .
H H9 0.3623 -0.8870 0.6560 0.116 Uiso calc R 1 . .
C C10 0.4657(3) -0.8309(4) 0.58615(16) 0.0944(8) Uani d . 1 . .
H H10 0.4305 -0.9603 0.5601 0.113 Uiso calc R 1 . .
C C11 0.5596(3) -0.6831(4) 0.56675(13) 0.0799(7) Uani d . 1 . .
H H11 0.5866 -0.7146 0.5277 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'
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
C2 S2 C1 . . 102.02(11) ?
C2 N1 N2 . . 121.39(18) ?
C2 N1 H1 . . 119.3 ?
N2 N1 H1 . . 119.3 ?
C3 N2 N1 . . 114.92(18) ?
S2 C1 H1A . . 109.5 ?
S2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
S2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 S1 . . 120.44(16) ?
N1 C2 S2 . . 113.58(15) ?
S1 C2 S2 . . 125.98(12) ?
N2 C3 C4 . . 121.2(2) ?
N2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 122.8(2) ?
C5 C4 H4 . . 118.6 ?
C3 C4 H4 . . 118.6 ?
C4 C5 C6 . . 126.9(2) ?
C4 C5 H5 . . 116.6 ?
C6 C5 H5 . . 116.6 ?
C7 C6 C11 . . 117.4(2) ?
C7 C6 C5 . . 123.05(18) ?
C11 C6 C5 . . 119.5(2) ?
C8 C7 C6 . . 121.1(2) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C9 C8 C7 . . 120.6(3) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C10 C9 C8 . . 119.7(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C6 . . 120.8(3) ?
C10 C11 H11 . . 119.6 ?
C6 C11 H11 . . 119.6 ?
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 C2 . 1.664(2) ?
S2 C2 . 1.741(2) ?
S2 C1 . 1.791(2) ?
N1 C2 . 1.339(3) ?
N1 N2 . 1.381(2) ?
N1 H1 . 0.8600 ?
N2 C3 . 1.287(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C4 . 1.428(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.335(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.454(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.392(3) ?
C6 C11 . 1.395(3) ?
C7 C8 . 1.376(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.372(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.363(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.388(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 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
_geom_hbond_publ_flag
N1 H1 S1 3_766 0.86 2.67 3.4086(19) 145 y
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
C2 N1 N2 C3 . . . . -177.27(18) ?
N2 N1 C2 S1 . . . . -175.70(15) ?
N2 N1 C2 S2 . . . . 4.4(2) ?
C1 S2 C2 N1 . . . . -177.67(16) ?
C1 S2 C2 S1 . . . . 2.41(18) ?
N1 N2 C3 C4 . . . . -176.76(18) ?
N2 C3 C4 C5 . . . . 178.9(2) ?
C3 C4 C5 C6 . . . . -174.93(19) ?
C4 C5 C6 C7 . . . . 7.9(3) ?
C4 C5 C6 C11 . . . . -173.6(2) ?
C11 C6 C7 C8 . . . . -0.5(3) ?
C5 C6 C7 C8 . . . . 178.1(2) ?
C6 C7 C8 C9 . . . . 0.6(4) ?
C7 C8 C9 C10 . . . . -0.4(4) ?
C8 C9 C10 C11 . . . . 0.1(4) ?
C9 C10 C11 C6 . . . . 0.0(4) ?
C7 C6 C11 C10 . . . . 0.2(3) ?
C5 C6 C11 C10 . . . . -178.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7837856
