#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/16/2011661.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_2011661
loop_
_publ_author_name
'Ren, Xiao-Ming'
'Xu, Yan'
'Hu, Chuan-Jiang'
'Meng, Qing-Jin'
'Lu, Chang-Sheng'
'Wang, Hua-Ting'
_publ_section_title
;
 2,3-Bis(4-nitrobenzylthio)maleonitrile
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1499
_journal_page_last               1500
_journal_paper_doi               10.1107/S010827010001283X
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C18 H12 N4 O4 S2'
_chemical_formula_weight         412.44
_chemical_name_systematic
;
 Bis(4-nitrobenzyl)maleonitriledithioether
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.456(6)
_cell_length_b                   15.440(3)
_cell_length_c                   8.1900(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      8.79
_cell_measurement_theta_min      1.68
_cell_volume                     3673.5(13)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'FR590 CAD-4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0162
_diffrn_reflns_av_sigmaI/netI    .0304
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3491
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.40
_diffrn_standards_decay_%        .0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .324
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .24
_refine_diff_density_max         .164
_refine_diff_density_min         -.178
_refine_ls_extinction_coef       .0017(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          .0663
_refine_ls_R_factor_gt           .0332
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0454P)²+2.8648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1004
_reflns_number_gt                2227
_reflns_number_total             3237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            sk1375.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3673.6(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2011661
_cod_database_fobs_code          2011661
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_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
_atom_site_type_symbol
S1 .13345(2) .32203(4) .11857(8) .05237(19) Uani d . 1 . . S
S2 .20796(2) .30507(4) -.10797(8) .0524(2) Uani d . 1 . . S
N2 .33696(8) .65987(15) .0285(3) .0594(6) Uani d . 1 . . N
C15 .03974(8) .27761(15) .0872(3) .0463(5) Uani d . 1 . . C
C8 .27203(7) .43007(14) -.1641(3) .0430(5) Uani d . 1 . . C
O4 .37613(8) .65487(15) .1055(3) .0851(7) Uani d . 1 . . O
C5 .15820(8) .36628(14) -.1722(3) .0445(5) Uani d . 1 . . C
C6 .24889(8) .34788(15) -.2312(3) .0488(6) Uani d . 1 . . C
H6A .2723 .3044 -.2378 .059 Uiso calc R 1 . . H
H6B .2329 .3585 -.3428 .059 Uiso calc R 1 . . H
C3 .08543(8) .42297(15) -.1286(3) .0543(6) Uani d . 1 . . C
O2 -.10169(7) .16278(16) -.2452(3) .0858(7) Uani d . 1 . . O
C11 .31496(8) .57963(15) -.0407(3) .0461(5) Uani d . 1 . . C
C17 .00946(9) .13808(17) -.0063(3) .0602(7) Uani d . 1 . . C
H17A .0128 .0783 -.0128 .072 Uiso calc R 1 . . H
C14 -.00122(8) .31492(17) .0138(3) .0569(6) Uani d . 1 . . C
H14A -.0051 .3745 .0214 .068 Uiso calc R 1 . . H
C2 .12549(7) .37206(14) -.0749(3) .0439(5) Uani d . 1 . . C
N4 .14756(9) .43232(16) -.4637(3) .0747(7) Uani d . 1 . . N
O3 .31547(8) .72727(13) .0082(3) .0828(6) Uani d . 1 . . O
C10 .27351(9) .58553(16) -.1444(3) .0550(6) Uani d . 1 . . C
H10A .2600 .6391 -.1720 .066 Uiso calc R 1 . . H
C18 -.03070(8) .17816(17) -.0790(3) .0519(6) Uani d . 1 . . C
C12 .33593(8) .50177(16) .0031(3) .0542(6) Uani d . 1 . . C
H12A .3642 .4994 .0729 .065 Uiso calc R 1 . . H
C4 .15138(8) .40423(15) -.3338(3) .0525(6) Uani d . 1 . . C
C9 .25237(8) .51031(15) -.2068(3) .0533(6) Uani d . 1 . . C
H9A .2245 .5133 -.2787 .064 Uiso calc R 1 . . H
C16 .04443(9) .18847(16) .0759(3) .0572(6) Uani d . 1 . . C
H16A .0717 .1623 .1248 .069 Uiso calc R 1 . . H
N1 -.06777(8) .12568(18) -.1724(3) .0685(6) Uani d . 1 . . N
C1 .07751(8) .33186(17) .1826(3) .0552(6) Uani d . 1 . . C
H1A .0807 .3163 .2987 .066 Uiso calc R 1 . . H
H1B .0681 .3921 .1727 .066 Uiso calc R 1 . . H
C13 -.03643(8) .26564(17) -.0704(3) .0582(7) Uani d . 1 . . C
H13A -.0637 .2915 -.1206 .070 Uiso calc R 1 . . H
N3 .05417(8) .46546(16) -.1708(4) .0817(8) Uani d . 1 . . N
C7 .31398(8) .42717(16) -.0592(3) .0512(6) Uani d . 1 . . C
H7A .3276 .3738 -.0302 .061 Uiso calc R 1 . . H
O1 -.06291(8) .04733(16) -.1738(3) .1020(8) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
_geom_angle_publ_flag
C2 S1 C1 103.48(12) yes
C5 S2 C6 103.65(11) yes
O3 N2 O4 123.4(2) ?
O3 N2 C11 118.9(2) ?
O4 N2 C11 117.7(2) ?
C14 C15 C16 118.3(2) ?
C14 C15 C1 120.8(2) ?
C16 C15 C1 120.9(2) ?
C7 C8 C9 118.5(2) ?
C7 C8 C6 120.3(2) ?
C9 C8 C6 121.1(2) ?
C2 C5 C4 120.9(2) yes
C2 C5 S2 120.13(17) yes
C4 C5 S2 118.79(19) yes
C8 C6 S2 113.98(17) ?
N3 C3 C2 178.2(3) yes
C10 C11 C12 122.5(2) ?
C10 C11 N2 118.3(2) ?
C12 C11 N2 119.2(2) ?
C16 C17 C18 118.5(2) ?
C13 C14 C15 121.3(2) ?
C5 C2 C3 119.3(2) yes
C5 C2 S1 120.32(17) yes
C3 C2 S1 120.35(19) yes
C11 C10 C9 118.4(2) ?
C13 C18 C17 121.7(2) ?
C13 C18 N1 119.0(2) ?
C17 C18 N1 119.2(2) ?
C11 C12 C7 118.2(2) ?
N4 C4 C5 177.0(3) yes
C10 C9 C8 121.0(2) ?
C17 C16 C15 121.3(2) ?
O1 N1 O2 123.4(3) ?
O1 N1 C18 118.3(2) ?
O2 N1 C18 118.3(3) ?
C15 C1 S1 115.59(17) ?
C18 C13 C14 118.9(2) ?
C12 C7 C8 121.3(2) ?
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 . 1.743(2) yes
S1 C1 . 1.816(2) yes
S2 C5 . 1.750(2) yes
S2 C6 . 1.820(2) yes
N2 O3 . 1.215(3) ?
N2 O4 . 1.222(3) ?
N2 C11 . 1.468(3) ?
C15 C14 . 1.382(3) ?
C15 C16 . 1.388(3) ?
C15 C1 . 1.504(3) ?
C8 C7 . 1.384(3) ?
C8 C9 . 1.388(3) ?
C8 C6 . 1.501(3) ?
C5 C2 . 1.351(3) yes
C5 C4 . 1.431(3) yes
C3 N3 . 1.137(3) yes
C3 C2 . 1.426(3) yes
O2 N1 . 1.219(3) ?
C11 C10 . 1.370(3) ?
C11 C12 . 1.372(3) ?
C17 C16 . 1.375(3) ?
C17 C18 . 1.380(3) ?
C14 C13 . 1.376(4) ?
N4 C4 . 1.137(3) yes
C10 C9 . 1.376(3) ?
C18 C13 . 1.364(4) ?
C18 N1 . 1.469(3) ?
C12 C7 . 1.377(3) ?
N1 O1 . 1.218(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105817
