#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/82/2218217.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_2218217
loop_
_publ_author_name
'Jiang, Yuqin'
'Wan, Xiangjian'
'Chen, Yongsheng'
_publ_section_title
;
 3-tert-Butyl-5,6,8-trinitronaphtho[1,8a,8-cd][1,2]dithiole
;
_journal_coeditor_code           PK2089
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o830
_journal_paper_doi               10.1107/S160053680800946X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H11 N3 O6 S2'
_chemical_formula_moiety         'C14 H11 N3 O6 S2'
_chemical_formula_sum            'C14 H11 N3 O6 S2'
_chemical_formula_weight         381.38
_chemical_name_systematic
;
3-tert-Butyl-5,6,8-trinitronaphtho[1,8a,8-cd][1,2]dithiole
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.909(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.477(3)
_cell_length_b                   20.754(4)
_cell_length_c                   8.1658(14)
_cell_measurement_reflns_used    2099
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.71
_cell_volume                     3174.4(10)
_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      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8118
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.374
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0382
_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)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1856
_reflns_number_total             2803
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2089.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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218217
_cod_database_fobs_code          2218217
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_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
S S1 0.22607(3) 0.26843(3) 0.74057(9) 0.0476(2) Uani d . 1
S S2 0.21867(3) 0.17028(3) 0.77160(9) 0.0490(2) Uani d . 1
O O1 -0.10572(11) 0.34597(11) 0.3300(3) 0.0838(7) Uani d . 1
O O2 -0.12517(9) 0.26776(9) 0.4864(2) 0.0525(5) Uani d . 1
O O3 -0.10009(10) 0.18790(11) 0.2446(2) 0.0661(6) Uani d . 1
O O4 -0.12944(10) 0.12220(10) 0.4212(3) 0.0665(6) Uani d . 1
O O5 0.08457(13) 0.00261(10) 0.7190(3) 0.1019(9) Uani d . 1
O O6 0.18753(12) 0.05183(10) 0.7857(3) 0.0809(7) Uani d . 1
N N1 -0.08510(11) 0.30111(12) 0.4295(3) 0.0494(6) Uani d . 1
N N2 -0.08763(12) 0.15858(12) 0.3800(3) 0.0513(6) Uani d . 1
N N3 0.12234(14) 0.05040(12) 0.7216(3) 0.0693(8) Uani d . 1
C C1 0.13641(12) 0.28171(11) 0.6422(3) 0.0349(6) Uani d . 1
C C2 0.09381(12) 0.22503(11) 0.6122(3) 0.0332(6) Uani d . 1
C C3 0.12897(13) 0.16621(11) 0.6715(3) 0.0378(6) Uani d . 1
C C4 0.08893(14) 0.10991(12) 0.6509(3) 0.0469(7) Uani d . 1
C C5 0.01708(14) 0.10991(13) 0.5605(3) 0.0487(7) Uani d . 1
H H5 -0.0084 0.0714 0.5431 0.058 Uiso calc R 1
C C6 -0.01603(12) 0.16565(12) 0.4978(3) 0.0402(6) Uani d . 1
C C7 0.01938(12) 0.22687(11) 0.5293(3) 0.0349(6) Uani d . 1
C C8 -0.00856(12) 0.28886(12) 0.4886(3) 0.0378(6) Uani d . 1
C C9 0.03362(13) 0.34351(12) 0.5203(3) 0.0418(6) Uani d . 1
H H9 0.0116 0.3831 0.4882 0.050 Uiso calc R 1
C C10 0.10644(13) 0.34324(12) 0.5964(3) 0.0388(6) Uani d . 1
C C11 0.14946(14) 0.40632(12) 0.6359(3) 0.0445(7) Uani d . 1
C C12 0.20882(15) 0.40735(14) 0.5453(4) 0.0603(8) Uani d . 1
H H12A 0.2363 0.4462 0.5746 0.090 Uiso calc R 1
H H12B 0.1880 0.4058 0.4244 0.090 Uiso calc R 1
H H12C 0.2394 0.3707 0.5803 0.090 Uiso calc R 1
C C13 0.18252(17) 0.41303(14) 0.8288(3) 0.0655(9) Uani d . 1
H H13A 0.2145 0.3777 0.8691 0.098 Uiso calc R 1
H H13B 0.1453 0.4127 0.8853 0.098 Uiso calc R 1
H H13C 0.2084 0.4529 0.8523 0.098 Uiso calc R 1
C C14 0.10141(16) 0.46540(13) 0.5768(4) 0.0678(9) Uani d . 1
H H14A 0.1295 0.5040 0.6038 0.102 Uiso calc R 1
H H14B 0.0643 0.4661 0.6338 0.102 Uiso calc R 1
H H14C 0.0804 0.4631 0.4560 0.102 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'
O O 0.0106 0.0060 '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 S1 S2 96.81(8)
C3 S2 S1 94.96(9)
O2 N1 O1 123.5(2)
O2 N1 C8 118.4(2)
O1 N1 C8 118.1(2)
O4 N2 O3 124.9(2)
O4 N2 C6 117.8(2)
O3 N2 C6 117.3(2)
O5 N3 O6 124.5(3)
O5 N3 C4 118.8(3)
O6 N3 C4 116.6(3)
C10 C1 C2 121.6(2)
C10 C1 S1 123.91(18)
C2 C1 S1 114.50(17)
C3 C2 C1 116.7(2)
C3 C2 C7 121.3(2)
C1 C2 C7 122.0(2)
C4 C3 C2 118.7(2)
C4 C3 S2 124.31(19)
C2 C3 S2 116.97(18)
C3 C4 C5 120.9(2)
C3 C4 N3 119.7(2)
C5 C4 N3 119.4(2)
C6 C5 C4 120.4(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 122.2(2)
C5 C6 N2 115.5(2)
C7 C6 N2 122.0(2)
C8 C7 C2 114.6(2)
C8 C7 C6 129.4(2)
C2 C7 C6 116.0(2)
C9 C8 C7 122.5(2)
C9 C8 N1 114.8(2)
C7 C8 N1 122.3(2)
C8 C9 C10 124.3(2)
C8 C9 H9 117.8
C10 C9 H9 117.8
C9 C10 C1 114.9(2)
C9 C10 C11 121.5(2)
C1 C10 C11 123.5(2)
C12 C11 C13 109.5(2)
C12 C11 C14 108.2(2)
C13 C11 C14 107.3(2)
C12 C11 C10 110.5(2)
C13 C11 C10 110.1(2)
C14 C11 C10 111.3(2)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.733(2)
S1 S2 2.0627(10)
S2 C3 1.716(2)
O1 N1 1.229(3)
O2 N1 1.226(3)
O3 N2 1.227(3)
O4 N2 1.223(3)
O5 N3 1.231(3)
O6 N3 1.234(3)
N1 C8 1.458(3)
N2 C6 1.468(3)
N3 C4 1.441(3)
C1 C10 1.411(3)
C1 C2 1.421(3)
C2 C3 1.419(3)
C2 C7 1.422(3)
C3 C4 1.389(3)
C4 C5 1.392(3)
C5 C6 1.355(3)
C5 H5 0.9300
C6 C7 1.435(3)
C7 C8 1.401(3)
C8 C9 1.383(3)
C9 C10 1.384(3)
C9 H9 0.9300
C10 C11 1.540(3)
C11 C12 1.534(4)
C11 C13 1.536(3)
C11 C14 1.538(4)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C1 S1 S2 C3 2.27(11)
S2 S1 C1 C10 176.23(18)
S2 S1 C1 C2 -2.85(17)
C10 C1 C2 C3 -176.8(2)
S1 C1 C2 C3 2.3(3)
C10 C1 C2 C7 2.3(3)
S1 C1 C2 C7 -178.63(16)
C1 C2 C3 C4 177.5(2)
C7 C2 C3 C4 -1.5(3)
C1 C2 C3 S2 -0.2(3)
C7 C2 C3 S2 -179.27(17)
S1 S2 C3 C4 -179.1(2)
S1 S2 C3 C2 -1.51(19)
C2 C3 C4 C5 5.7(4)
S2 C3 C4 C5 -176.7(2)
C2 C3 C4 N3 -175.3(2)
S2 C3 C4 N3 2.3(4)
O5 N3 C4 C3 171.9(3)
O6 N3 C4 C3 -6.0(4)
O5 N3 C4 C5 -9.0(4)
O6 N3 C4 C5 173.0(3)
C3 C4 C5 C6 -3.2(4)
N3 C4 C5 C6 177.8(2)
C4 C5 C6 C7 -3.7(4)
C4 C5 C6 N2 169.7(2)
O4 N2 C6 C5 46.7(3)
O3 N2 C6 C5 -130.7(3)
O4 N2 C6 C7 -139.9(2)
O3 N2 C6 C7 42.7(3)
C3 C2 C7 C8 175.8(2)
C1 C2 C7 C8 -3.2(3)
C3 C2 C7 C6 -4.8(3)
C1 C2 C7 C6 176.2(2)
C5 C6 C7 C8 -173.2(2)
N2 C6 C7 C8 13.8(4)
C5 C6 C7 C2 7.6(3)
N2 C6 C7 C2 -165.4(2)
C2 C7 C8 C9 2.6(3)
C6 C7 C8 C9 -176.7(2)
C2 C7 C8 N1 -169.64(19)
C6 C7 C8 N1 11.1(4)
O2 N1 C8 C9 -138.7(2)
O1 N1 C8 C9 38.6(3)
O2 N1 C8 C7 34.1(3)
O1 N1 C8 C7 -148.6(3)
C7 C8 C9 C10 -1.0(4)
N1 C8 C9 C10 171.8(2)
C8 C9 C10 C1 -0.2(4)
C8 C9 C10 C11 -176.9(2)
C2 C1 C10 C9 -0.5(3)
S1 C1 C10 C9 -179.49(17)
C2 C1 C10 C11 176.2(2)
S1 C1 C10 C11 -2.8(3)
C9 C10 C11 C12 -121.4(3)
C1 C10 C11 C12 62.2(3)
C9 C10 C11 C13 117.6(3)
C1 C10 C11 C13 -58.8(3)
C9 C10 C11 C14 -1.2(3)
C1 C10 C11 C14 -177.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21117921
