#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/32/2103280.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_2103280
loop_
_publ_author_name
'Farrell, Dorcas M. M.'
'Glidewell, Christopher'
'Low, John N.'
'Skakle, Janet M. S.'
'Zakaria, Choudhury M.'
_publ_section_title
;
 Polymorphs and pseudopolymorphs of
 N,N'-dithiobisphthalimide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              289
_journal_page_last               299
_journal_paper_doi               10.1107/S0108768101020006
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C16 H8 N2 O4 S2, 0.5(C7 H8)'
_chemical_formula_sum            'C19.5 H12 N2 O4 S2'
_chemical_formula_weight         402.45
_chemical_name_systematic
;
N,N'-Dithiodiphthalimide hemi(toluene) solvate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.3216(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3126(4)
_cell_length_b                   16.1270(4)
_cell_length_c                   7.6990(2)
_cell_measurement_reflns_used    3467
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.92
_cell_volume                     1772.03(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9295
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0598P)²+0.3414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2827
_reflns_number_total             3467
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0132.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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      P21/n
_cod_database_code               2103280
_cod_database_fobs_code          2103280
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_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
S11 0.45099(3) 0.56413(3) 0.84701(6) 0.02201(15) Uani d . 1 . . S
N11 0.36287(9) 0.62401(9) 0.78652(18) 0.0183(3) Uani d . 1 . . N
C11 0.35383(11) 0.71011(10) 0.8215(2) 0.0177(4) Uani d . 1 . . C
O11 0.41027(8) 0.75112(7) 0.89157(16) 0.0254(3) Uani d . 1 . . O
C12 0.28390(11) 0.59261(11) 0.7018(2) 0.0181(4) Uani d . 1 . . C
O12 0.27627(9) 0.52211(7) 0.65630(17) 0.0280(3) Uani d . 1 . . O
C13 0.22172(11) 0.66510(10) 0.6876(2) 0.0171(4) Uani d . 1 . . C
C14 0.13540(12) 0.67066(11) 0.6173(2) 0.0218(4) Uani d . 1 . . C
C15 0.09288(12) 0.74823(11) 0.6175(2) 0.0243(4) Uani d . 1 . . C
C16 0.13516(12) 0.81782(11) 0.6836(2) 0.0222(4) Uani d . 1 . . C
C17 0.22203(12) 0.81232(11) 0.7543(2) 0.0200(4) Uani d . 1 . . C
C18 0.26316(11) 0.73477(10) 0.7558(2) 0.0168(4) Uani d . 1 . . C
S21 0.54978(3) 0.56663(3) 0.64296(6) 0.02252(15) Uani d . 1 . . S
N21 0.62373(10) 0.64399(9) 0.68640(19) 0.0200(3) Uani d . 1 . . N
C21 0.61335(12) 0.72849(11) 0.6353(2) 0.0195(4) Uani d . 1 . . C
O21 0.54773(9) 0.75469(8) 0.56332(16) 0.0270(3) Uani d . 1 . . O
C22 0.70713(11) 0.63222(11) 0.7743(2) 0.0180(4) Uani d . 1 . . C
O22 0.72952(9) 0.56787(7) 0.83850(17) 0.0251(3) Uani d . 1 . . O
C23 0.75400(11) 0.71398(10) 0.7688(2) 0.0170(4) Uani d . 1 . . C
C24 0.83880(12) 0.73624(11) 0.8317(2) 0.0197(4) Uani d . 1 . . C
C25 0.86557(13) 0.81908(11) 0.8146(2) 0.0228(4) Uani d . 1 . . C
C26 0.80857(13) 0.87663(11) 0.7380(2) 0.0235(4) Uani d . 1 . . C
C27 0.72397(13) 0.85359(11) 0.6737(2) 0.0212(4) Uani d . 1 . . C
C28 0.69815(11) 0.77117(10) 0.6900(2) 0.0177(4) Uani d . 1 . . C
C31 0.97524(13) 0.53541(13) 0.3440(3) 0.0312(5) Uani d . 1 . . C
C32 0.92401(13) 0.55233(12) 0.5000(3) 0.0319(5) Uani d . 1 B . C
C33 0.94843(13) 0.51694(12) 0.6542(3) 0.0289(4) Uani d . 1 . . C
C34 0.9462(3) 0.5640(3) 0.1649(5) 0.0336(10) Uani d P 0.50 B -2 C
H14 0.1033 0.6236 0.5683 0.026 Uiso calc R 1 . . H
H15 0.0302 0.7527 0.5682 0.029 Uiso calc R 1 . . H
H16 0.1031 0.8694 0.6792 0.027 Uiso calc R 1 . . H
H17 0.2546 0.8594 0.8019 0.024 Uiso calc R 1 . . H
H24 0.8805 0.6969 0.8871 0.024 Uiso calc R 1 . . H
H25 0.9266 0.8353 0.8590 0.027 Uiso calc R 1 . . H
H26 0.8284 0.9326 0.7300 0.028 Uiso calc R 1 . . H
H27 0.6820 0.8926 0.6178 0.025 Uiso calc R 1 . . H
H31 0.9546 0.5618 0.2376 0.037 Uiso calc PR 0.50 A -1 H
H32 0.8723 0.5894 0.4905 0.038 Uiso calc R 1 . . H
H33 0.9156 0.5271 0.7548 0.035 Uiso calc R 1 B . H
H34A 0.9948 0.5496 0.0870 0.050 Uiso calc PR 0.50 B -2 H
H34B 0.9374 0.6243 0.1652 0.050 Uiso calc PR 0.50 B -2 H
H34C 0.8872 0.5370 0.1242 0.050 Uiso calc PR 0.50 B -2 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N11 S11 S21 . . 108.16(6) no
C12 N11 C11 . . 111.7(2) no
C12 N11 S11 . . 121.0(2) no
C11 N11 S11 . . 127.2(2) no
O11 C11 C18 . . 127.0(2) no
O11 C11 N11 . . 125.5(2) no
C18 C11 N11 . . 107.5(2) no
O12 C12 N11 . . 123.4(2) no
O12 C12 C13 . . 134.1(2) no
N11 C12 C13 . . 102.5(2) no
C14 C13 C18 . . 118.2(2) no
C14 C13 C12 . . 129.1(2) no
C18 C13 C12 . . 112.7(2) no
C13 C14 C15 . . 117.3(2) no
C13 C14 H14 . . 121.3 no
C15 C14 H14 . . 121.3 no
C16 C15 C14 . . 124.2(2) no
C16 C15 H15 . . 117.9 no
C14 C15 H15 . . 117.9 no
C17 C16 C15 . . 118.6(2) no
C17 C16 H16 . . 120.7 no
C15 C16 H16 . . 120.7 no
C16 C17 C18 . . 116.8(2) no
C16 C17 H17 . . 121.6 no
C18 C17 H17 . . 121.6 no
C13 C18 C17 . . 124.9(2) no
C13 C18 C11 . . 105.6(2) no
C17 C18 C11 . . 129.5(2) no
N21 S21 S11 . . 107.85(6) no
C22 N21 C21 . . 110.2(2) no
C22 N21 S21 . . 121.8(2) no
C21 N21 S21 . . 127.9(2) no
O21 C21 N21 . . 123.8(2) no
O21 C21 C28 . . 128.1(2) no
N21 C21 C28 . . 108.1(2) no
O22 C22 N21 . . 122.5(2) no
O22 C22 C23 . . 133.1(2) no
N21 C22 C23 . . 104.3(2) no
C24 C23 C28 . . 118.7(2) no
C24 C23 C22 . . 129.5(2) no
C28 C23 C22 . . 111.8(2) no
C23 C24 C25 . . 118.4(2) no
C23 C24 H24 . . 120.8 no
C25 C24 H24 . . 120.8 no
C26 C25 C24 . . 122.7(2) no
C26 C25 H25 . . 118.7 no
C24 C25 H25 . . 118.7 no
C27 C26 C25 . . 118.5(2) no
C27 C26 H26 . . 120.7 no
C25 C26 H26 . . 120.7 no
C26 C27 C28 . . 118.5(2) no
C26 C27 H27 . . 120.8 no
C28 C27 H27 . . 120.8 no
C23 C28 C27 . . 123.2(2) no
C23 C28 C21 . . 105.5(2) no
C27 C28 C21 . . 131.3(2) no
C33 C31 C34 3_766 . 111.4(2) no
C33 C31 C32 3_766 . 123.1(2) no
C34 C31 C32 . . 125.2(2) no
C33 C31 H31 3_766 . 118.5 no
C32 C31 H31 . . 118.5 no
C33 C32 C31 . . 121.9(2) no
C33 C32 H32 . . 119.0 no
C31 C32 H32 . . 119.0 no
C32 C33 C31 . 3_766 115.0(2) no
C32 C33 H33 . . 122.5 no
C31 C33 H33 3_766 . 122.5 no
C31 C34 H34A . . 109.5 no
C31 C34 H34B . . 109.5 no
H34A C34 H34B . . 109.5 no
C31 C34 H34C . . 109.5 no
H34A C34 H34C . . 109.5 no
H34B C34 H34C . . 109.5 no
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
S11 N11 . 1.628(2) no
S11 S21 . 2.1918(7) no
N11 C12 . 1.360(2) no
N11 C11 . 1.422(2) no
C11 O11 . 1.147(2) no
C11 C18 . 1.414(2) no
C12 O12 . 1.192(2) no
C12 C13 . 1.468(2) no
C13 C14 . 1.314(2) no
C13 C18 . 1.358(2) no
C14 C15 . 1.391(3) no
C14 H14 . 0.9500 no
C15 C16 . 1.356(3) no
C15 H15 . 0.9500 no
C16 C17 . 1.322(2) no
C16 H16 . 0.9500 no
C17 C18 . 1.382(2) no
C17 H17 . 0.9500 no
S21 N21 . 1.654(2) no
N21 C22 . 1.341(2) no
N21 C21 . 1.423(2) no
C21 O21 . 1.136(2) no
C21 C28 . 1.431(2) no
C22 O22 . 1.183(2) no
C22 C23 . 1.481(2) no
C23 C24 . 1.322(2) no
C23 C28 . 1.336(2) no
C24 C25 . 1.399(3) no
C24 H24 . 0.9500 no
C25 C26 . 1.342(3) no
C25 H25 . 0.9500 no
C26 C27 . 1.326(3) no
C26 H26 . 0.9500 no
C27 C28 . 1.388(2) no
C27 H27 . 0.9500 no
C31 C33 3_766 1.380(3) no
C31 C34 . 1.483(4) no
C31 C32 . 1.479(3) no
C31 H31 . 0.9500 no
C32 C33 . 1.340(3) no
C32 H32 . 0.9500 no
C33 C31 3_766 1.380(3) no
C33 H33 . 0.9500 no
C34 H34A . 0.9800 no
C34 H34B . 0.9800 no
C34 H34C . 0.9800 no
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
C15 H15 O11 4_464 0.95 2.11 3.029(2) 163 y
C26 H26 O22 2_656 0.95 2.38 3.179(2) 142 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_4
_geom_torsion
_geom_torsion_publ_flag
S21 S11 N11 C12 . . 94.3(2) no
S21 S11 N11 C11 . . -90.2(2) no
C12 N11 C11 O11 . . 179.9(2) no
S11 N11 C11 O11 . . 3.9(3) no
C12 N11 C11 C18 . . 0.4(2) no
S11 N11 C11 C18 . . -175.5(2) no
C11 N11 C12 O12 . . 178.5(2) no
S11 N11 C12 O12 . . -5.3(2) no
C11 N11 C12 C13 . . -1.2(2) no
S11 N11 C12 C13 . . 175.1(2) no
O12 C12 C13 C14 . . 0.7(3) no
N11 C12 C13 C14 . . -179.7(2) no
O12 C12 C13 C18 . . -178.0(2) no
N11 C12 C13 C18 . . 1.6(2) no
C18 C13 C14 C15 . . 0.3(3) no
C12 C13 C14 C15 . . -178.4(2) no
C13 C14 C15 C16 . . 0.7(3) no
C14 C15 C16 C17 . . -0.7(3) no
C15 C16 C17 C18 . . -0.3(3) no
C14 C13 C18 C17 . . -1.3(3) no
C12 C13 C18 C17 . . 177.6(2) no
C14 C13 C18 C11 . . 179.8(2) no
C12 C13 C18 C11 . . -1.4(2) no
C16 C17 C18 C13 . . 1.3(3) no
C16 C17 C18 C11 . . 180.0(2) no
O11 C11 C18 C13 . . -178.9(2) no
N11 C11 C18 C13 . . 0.6(2) no
O11 C11 C18 C17 . . 2.3(3) no
N11 C11 C18 C17 . . -178.3(2) no
N11 S11 S21 N21 . . 89.05(8) no
S11 S21 N21 C22 . . 95.1(2) no
S11 S21 N21 C21 . . -87.5(2) no
C22 N21 C21 O21 . . -177.8(2) no
S21 N21 C21 O21 . . 4.6(3) no
C22 N21 C21 C28 . . 2.4(2) no
S21 N21 C21 C28 . . -175.2(2) no
C21 N21 C22 O22 . . 175.7(2) no
S21 N21 C22 O22 . . -6.6(2) no
C21 N21 C22 C23 . . -3.3(2) no
S21 N21 C22 C23 . . 174.5(2) no
O22 C22 C23 C24 . . 3.2(3) no
N21 C22 C23 C24 . . -178.0(2) no
O22 C22 C23 C28 . . -175.5(2) no
N21 C22 C23 C28 . . 3.3(2) no
C28 C23 C24 C25 . . 0.9(3) no
C22 C23 C24 C25 . . -177.8(2) no
C23 C24 C25 C26 . . 0.3(3) no
C24 C25 C26 C27 . . -1.0(3) no
C25 C26 C27 C28 . . 0.5(3) no
C24 C23 C28 C27 . . -1.4(3) no
C22 C23 C28 C27 . . 177.5(2) no
C24 C23 C28 C21 . . 179.3(2) no
C22 C23 C28 C21 . . -1.9(2) no
C26 C27 C28 C23 . . 0.7(3) no
C26 C27 C28 C21 . . 179.8(2) no
O21 C21 C28 C23 . . 180.0(2) no
N21 C21 C28 C23 . . -0.2(2) no
O21 C21 C28 C27 . . 0.7(3) no
N21 C21 C28 C27 . . -179.5(2) no
C33 C31 C32 C33 3_766 . -0.5(3) no
C34 C31 C32 C33 . . 172.4(3) no
C31 C32 C33 C31 . 3_766 0.5(3) no
