#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006437.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_2006437
loop_
_publ_author_name
'Cun-Yuan Zhao'
'Chun-Ying Duan'
'Yu-Peng Tian'
'Xiao-Zeng You'
'Thomas C. W. Mak'
_publ_section_title
;
 S-Methyl
 β-N-[4-(Dimethylamino)benzylidene]dithiocarbazate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1151
_journal_page_last               1153
_journal_paper_doi               10.1107/S0108270197004691
_journal_volume                  53
_journal_year                    1997
_chemical_formula_structural     NMe2-C6H4-CH=N-N-CSSMe
_chemical_formula_sum            'C11 H15 N3 S2'
_chemical_formula_weight         253.40
_chemical_name_common
S-methyl-(-N-(dimethylaminophenyl)-methylenedithiocarbazate
_chemical_name_systematic        ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.364(2)
_cell_length_b                   12.684(3)
_cell_length_c                   12.224(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      18
_cell_measurement_theta_min      11
_cell_volume                     1295.7(5)
_computing_data_collection       'SHELXTL-Plus (Sheldrick, 1987)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_structure_refinement  SHELXS-86
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measurement_device       'Rigaku AFC7R 4-circle-diffractometer'
_diffrn_measurement_method       'Profile-fitted ω 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  0.0561
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3165
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%        0.965
_diffrn_standards_interval_time  97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.360
_refine_ls_extinction_coef       0.0010(4)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.080
_refine_ls_hydrogen_treatment
'H atoms refined as riding model, with U~iso~ fixed'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1982
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_obs          .0789
_refine_ls_shift/esd_max         0.083
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/σ²(Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0803
_refine_ls_wR_factor_obs         .0852
_reflns_number_observed          1982
_reflns_number_total             2970
_reflns_observed_criterion       >6sigma(F)
_cod_data_source_file            ta1150.cif
_cod_data_source_block           l5
_cod_depositor_comments
;
 Changing the space group from '-P 2bc' to '-P 2yn' after consulting the
 original publication. All related space group information was changed
 accordingly.

 Antanas Vaitkus,
 2017-07-04

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/\s^2^(Fo^2^)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/\s^2^(Fo^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1295.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2006437
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 .0560(10) .0650(10) .0860(10) .0000(10) .0250(10) .0020(10)
S2 .0740(10) .0670(10) .0770(10) -.0090(10) .0180(10) .0050(10)
N1 .0550(10) .0650(10) .0790(10) -.0070(10) .0240(10) .0000(10)
N2 .0570(10) .0700(10) .0690(10) -.0010(10) .0190(10) .0050(10)
N3 .0660(10) .0800(10) .0970(10) -.0020(10) .0340(10) -.0020(10)
C1 .0560(10) .0540(10) .0610(10) -.0020(10) .0090(10) .0070(10)
C2 .0550(10) .0680(10) .0660(10) -.0020(10) .0150(10) .0060(10)
C3 .0590(10) .0660(10) .0710(10) -.0050(10) .0160(10) -.0060(10)
C4 .0650(10) .0630(10) .0750(10) -.0110(10) .0230(10) .0010(10)
C5 .0550(10) .0690(10) .0610(10) .0040(10) .0150(10) .0020(10)
C6 .0580(10) .0600(10) .0730(10) .0020(10) .0120(10) -.0060(10)
C7 .0610(10) .0590(10) .0660(10) -.0010(10) .0130(10) .0030(10)
C8 .0510(10) .0630(10) .0590(10) .0020(10) .0080(10) .0050(10)
C9 .0790(10) .0900(10) .1060(10) -.0010(10) .0460(10) .0120(10)
C10 .0670(10) .0980(10) .0980(10) .0050(10) .0240(10) -.0120(10)
C11 .0900(10) .0690(10) .0950(10) -.0050(10) .0100(10) -.0130(10)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 .11230(10) .65440(10) .46520(10) .0680(10) Uani d . 1 . S
S2 -.08480(10) .80600(10) .59450(10) .0720(10) Uani d . 1 . S
N1 -.1564(3) .6103(3) .5567(3) .0660(10) Uani d . 1 . N
N2 -.2906(3) .6346(3) .6139(3) .0650(10) Uani d . 1 . N
N3 -.9723(4) .5896(3) .8383(3) .0800(10) Uani d . 1 . N
C1 -.0455(4) .6829(3) .5381(3) .0570(10) Uani d . 1 . C
C2 -.3909(4) .5589(3) .6213(3) .0630(10) Uani d . 1 . C
C3 -.5791(4) .6605(3) .7356(3) .0650(10) Uani d . 1 . C
C4 -.7220(4) .6670(3) .7876(3) .0670(10) Uani d . 1 . C
C5 -.8321(4) .5828(3) .7846(3) .0610(10) Uani d . 1 . C
C6 -.7923(4) .4927(3) .7258(3) .0630(10) Uani d . 1 . C
C7 -.6477(4) .4866(3) .6747(3) .0620(10) Uani d . 1 . C
C8 -.5392(4) .5696(3) .6780(3) .0580(10) Uani d . 1 . C
C9 -1.0181(5) .6849(4) .8925(4) .0900(10) Uani d . 1 . C
C10 -1.0812(5) .5008(4) .8417(4) .0870(10) Uani d . 1 . C
C11 .0850(5) .8787(4) .5515(4) .0840(10) Uani d . 1 . C
H1A -.1433 .5442 .5318 .080 Uiso calc R 1 . H
H2B -.3684 .4932 .5861 .080 Uiso calc R 1 . H
H3A -.5065 .7192 .7386 .080 Uiso calc R 1 . H
H4A -.7465 .7299 .8273 .080 Uiso calc R 1 . H
H6A -.8659 .4346 .7211 .080 Uiso calc R 1 . H
H7A -.6220 .4236 .6357 .080 Uiso calc R 1 . H
H9A -.9377 .7380 .8841 .080 Uiso calc R 1 . H
H9B -1.1186 .7098 .8618 .080 Uiso calc R 1 . H
H9C -1.0283 .6700 .9689 .080 Uiso calc R 1 . H
H10A -1.0374 .4432 .8016 .080 Uiso calc R 1 . H
H10B -1.0934 .4800 .9164 .080 Uiso calc R 1 . H
H10C -1.1836 .5198 .8093 .080 Uiso calc R 1 . H
H11A .0793 .9499 .5778 .080 Uiso calc R 1 . H
H11B .1807 .8460 .5816 .080 Uiso calc R 1 . H
H11C .0865 .8786 .4734 .080 Uiso calc R 1 . H
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
C1 S2 C11 100.5(2)
N2 N1 C1 121.2(3)
N1 N2 C2 114.6(3)
C5 N3 C9 121.5(3)
C5 N3 C10 121.0(4)
C9 N3 C10 117.4(4)
S1 C1 S2 125.0(2)
S1 C1 N1 121.0(3)
S2 C2 N1 114.0(3)
N2 C2 C8 122.6(3)
C4 C3 C8 120.7(3)
C3 C4 C5 121.3(3)
N3 C5 C4 120.7(3)
N3 C5 C6 121.6(3)
C4 C5 C6 117.7(3)
C5 C6 C7 120.5(3)
C6 C7 C8 121.7(3)
C2 C8 C3 122.9(3)
C2 C8 C7 119.0(3)
C3 C8 C7 118.7(3)
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 C1 . 1.663(4) ?
S2 C1 . 1.744(4) ?
S2 C11 . 1.788(5) ?
N1 N2 . 1.381(4) ?
N1 C1 . 1.333(5) ?
N2 C2 . 1.281(5) ?
N3 C5 . 1.371(5) ?
N3 C9 . 1.438(6) ?
N3 C10 . 1.450(6) ?
C2 C8 . 1.452(5) ?
C3 C4 . 1.380(5) ?
C3 C8 . 1.399(5) ?
C4 C5 . 1.410(5) ?
C5 C6 . 1.397(5) ?
C6 C7 . 1.387(5) ?
C7 C8 . 1.389(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5279366
