#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/46/2234668.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_2234668
loop_
_publ_author_name
'Tayamon, Shahedeh'
'Ravoof, Thahira Begum S. A.'
'Tahir, Mohamed Ibrahim Mohamed'
'Crouse, Karen A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Benzyl 3-(2-methylphenyl)dithiocarbazate
;
_journal_coeditor_code           HG5209
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1402
_journal_paper_doi               10.1107/S160053681201567X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H16 N2 S2'
_chemical_formula_moiety         'C15 H16 N2 S2'
_chemical_formula_sum            'C15 H16 N2 S2'
_chemical_formula_weight         288.42
_chemical_name_common
;
N-{[(Benzylsulfanyl)methanethioyl]amino}-2-methylaniline
;
_chemical_name_systematic
;
Benzyl 3-(2-methylphenyl)dithiocarbazate
;
_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                 95.198(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.70000(10)
_cell_length_b                   11.0136(2)
_cell_length_c                   22.7545(4)
_cell_measurement_reflns_used    8863
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71
_cell_measurement_theta_min      4
_cell_volume                     1422.60(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1952
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Oxford Diffraction Xcaliber Eos Gemini'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15011
_diffrn_reflns_theta_full        71.46
_diffrn_reflns_theta_max         71.46
_diffrn_reflns_theta_min         3.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.274
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'
_exptl_crystal_colour            dark-yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0349
_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)+(0.0646P)²+0.6201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2560
_reflns_number_total             2725
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5209.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2234668
_cod_database_fobs_code          2234668
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
S S1 0.96691(6) 0.83305(3) 0.582743(16) 0.02154(13) Uani d . 1 1
S S2 0.73047(7) 0.64766(4) 0.498745(16) 0.02497(14) Uani d . 1 1
N N1 1.1403(2) 0.62113(12) 0.56054(6) 0.0234(3) Uani d D 1 1
H H1n 1.153(3) 0.5503(11) 0.5436(8) 0.028 Uiso d D 1 1
N N2 1.3086(2) 0.65256(12) 0.60680(6) 0.0226(3) Uani d D 1 1
H H2n 1.446(2) 0.6572(17) 0.5924(8) 0.027 Uiso d D 1 1
C C1 0.6928(3) 0.90389(14) 0.55250(7) 0.0247(3) Uani d . 1 1
H H1A 0.6944 0.9153 0.5094 0.030 Uiso calc R 1 1
H H1B 0.5571 0.8516 0.5597 0.030 Uiso calc R 1 1
C C2 0.6713(3) 1.02493(14) 0.58237(6) 0.0216(3) Uani d . 1 1
C C3 0.8217(3) 1.12038(16) 0.57225(7) 0.0277(4) Uani d . 1 1
H H3 0.9444 1.1086 0.5472 0.033 Uiso calc R 1 1
C C4 0.7947(3) 1.23226(16) 0.59816(8) 0.0314(4) Uani d . 1 1
H H4 0.8989 1.2967 0.5908 0.038 Uiso calc R 1 1
C C5 0.6166(3) 1.25144(15) 0.63490(7) 0.0285(4) Uani d . 1 1
H H5 0.5978 1.3288 0.6524 0.034 Uiso calc R 1 1
C C6 0.4669(3) 1.15700(15) 0.64578(8) 0.0279(4) Uani d . 1 1
H H6 0.3445 1.1693 0.6709 0.033 Uiso calc R 1 1
C C7 0.4950(3) 1.04384(15) 0.62004(7) 0.0252(3) Uani d . 1 1
H H7 0.3931 0.9789 0.6282 0.030 Uiso calc R 1 1
C C8 0.9545(3) 0.69201(14) 0.54650(6) 0.0206(3) Uani d . 1 1
C C9 1.3110(3) 0.57463(14) 0.65724(7) 0.0211(3) Uani d . 1 1
C C10 1.4934(3) 0.59097(14) 0.70252(7) 0.0231(3) Uani d . 1 1
C C11 1.4978(3) 0.51509(15) 0.75165(7) 0.0272(3) Uani d . 1 1
H H11 1.6205 0.5243 0.7825 0.033 Uiso calc R 1 1
C C12 1.3278(3) 0.42639(16) 0.75675(7) 0.0294(4) Uani d . 1 1
H H12 1.3361 0.3745 0.7902 0.035 Uiso calc R 1 1
C C13 1.1459(3) 0.41438(16) 0.71253(7) 0.0288(4) Uani d . 1 1
H H13 1.0267 0.3553 0.7161 0.035 Uiso calc R 1 1
C C14 1.1371(3) 0.48843(15) 0.66296(7) 0.0250(3) Uani d . 1 1
H H14 1.0114 0.4800 0.6328 0.030 Uiso calc R 1 1
C C15 1.6766(3) 0.68749(16) 0.69763(7) 0.0288(4) Uani d . 1 1
H H15A 1.7773 0.6925 0.7348 0.043 Uiso calc R 1 1
H H15B 1.5991 0.7659 0.6894 0.043 Uiso calc R 1 1
H H15C 1.7730 0.6670 0.6655 0.043 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C8 S1 C1 101.79(7)
C8 N1 N2 120.74(13)
C8 N1 H1n 120.8(13)
N2 N1 H1n 118.2(13)
N1 N2 C9 114.19(12)
N1 N2 H2n 108.0(13)
C9 N2 H2n 112.9(13)
C2 C1 S1 108.06(10)
C2 C1 H1A 110.1
S1 C1 H1A 110.1
C2 C1 H1B 110.1
S1 C1 H1B 110.1
H1A C1 H1B 108.4
C3 C2 C7 118.62(15)
C3 C2 C1 121.22(14)
C7 C2 C1 120.15(14)
C4 C3 C2 120.69(15)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.58(16)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 119.37(15)
C6 C5 H5 120.3
C4 C5 H5 120.3
C5 C6 C7 120.12(16)
C5 C6 H6 119.9
C7 C6 H6 119.9
C2 C7 C6 120.61(15)
C2 C7 H7 119.7
C6 C7 H7 119.7
N1 C8 S2 121.91(12)
N1 C8 S1 114.11(11)
S2 C8 S1 123.98(9)
C14 C9 C10 120.37(14)
C14 C9 N2 122.02(14)
C10 C9 N2 117.57(14)
C11 C10 C9 117.97(15)
C11 C10 C15 121.44(14)
C9 C10 C15 120.59(14)
C12 C11 C10 121.78(15)
C12 C11 H11 119.1
C10 C11 H11 119.1
C13 C12 C11 119.28(15)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 120.25(16)
C12 C13 H13 119.9
C14 C13 H13 119.9
C9 C14 C13 120.29(15)
C9 C14 H14 119.9
C13 C14 H14 119.9
C10 C15 H15A 109.5
C10 C15 H15B 109.5
H15A C15 H15B 109.5
C10 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.7571(15)
S1 C1 1.8247(16)
S2 C8 1.6729(15)
N1 C8 1.331(2)
N1 N2 1.4020(17)
N1 H1n 0.877(9)
N2 C9 1.432(2)
N2 H2n 0.878(9)
C1 C2 1.506(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.389(2)
C2 C7 1.394(2)
C3 C4 1.381(2)
C3 H3 0.9500
C4 C5 1.389(3)
C4 H4 0.9500
C5 C6 1.382(2)
C5 H5 0.9500
C6 C7 1.392(2)
C6 H6 0.9500
C7 H7 0.9500
C9 C14 1.387(2)
C9 C10 1.407(2)
C10 C11 1.394(2)
C10 C15 1.501(2)
C11 C12 1.388(2)
C11 H11 0.9500
C12 C13 1.384(2)
C12 H12 0.9500
C13 C14 1.389(2)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 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
N1 H1n S2 3_766 0.876(14) 2.498(14) 3.3625(14) 169.3(15)
N2 H2n S2 1_655 0.877(13) 2.794(16) 3.5919(13) 151.9(14)
C11 H11 Cg1 2_746 0.95 2.98 3.8594(18) 155
C5 H5 Cg2 1_465 0.95 2.84 3.7005(18) 151
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
C8 N1 N2 C9 111.24(16)
C8 S1 C1 C2 176.89(11)
S1 C1 C2 C3 68.74(16)
S1 C1 C2 C7 -112.65(14)
C7 C2 C3 C4 -1.1(2)
C1 C2 C3 C4 177.55(15)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 0.5(3)
C4 C5 C6 C7 0.0(2)
C3 C2 C7 C6 1.6(2)
C1 C2 C7 C6 -177.07(14)
C5 C6 C7 C2 -1.0(2)
N2 N1 C8 S2 -170.63(11)
N2 N1 C8 S1 8.92(19)
C1 S1 C8 N1 179.22(12)
C1 S1 C8 S2 -1.24(12)
N1 N2 C9 C14 -9.7(2)
N1 N2 C9 C10 172.43(13)
C14 C9 C10 C11 2.4(2)
N2 C9 C10 C11 -179.66(14)
C14 C9 C10 C15 -177.54(14)
N2 C9 C10 C15 0.4(2)
C9 C10 C11 C12 -0.6(2)
C15 C10 C11 C12 179.38(15)
C10 C11 C12 C13 -1.4(2)
C11 C12 C13 C14 1.5(2)
C10 C9 C14 C13 -2.3(2)
N2 C9 C14 C13 179.88(14)
C12 C13 C14 C9 0.3(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657693
