#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/64/2216417.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_2216417
loop_
_publ_author_name
'Chojnacki, Jaroslaw'
'Skop, Patrycja'
'Pladzyk, Agnieszka'
'Nycz, Jacek E.'
_publ_section_title
;(7Z,7'Z)-2,2-Dimethyl-7,7'-(1,2,4-trithiolane-3,5-diylidene)bis[quinolin-8(7H)-one]
 chloroform disolvate
;
_journal_coeditor_code           DN2267
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4773
_journal_page_last               o4774
_journal_paper_doi               10.1107/S1600536807058217
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H14 N2 O2 S3, 2C H Cl3'
_chemical_formula_moiety         'C22 H14 N2 O2 S3, 2(C H Cl3)'
_chemical_formula_sum            'C24 H16 Cl6 N2 O2 S3'
_chemical_formula_weight         673.27
_chemical_name_systematic
;
(7Z,7'Z)-2,2-Dimethyl-7,7'-(1,2,4-trithiolane-3,5-diylidene)bis[quinolin-
8(7H)-one] chloroform disolvate
;
_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
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.149(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.7359(13)
_cell_length_b                   10.6749(6)
_cell_length_c                   11.1128(6)
_cell_measurement_reflns_used    6056
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      1.5
_cell_measurement_theta_min      30.6
_cell_volume                     2730.3(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2006)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'KM4CCD, Oxford Diffraction'
_diffrn_measurement_method       '0.75° ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9483
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.1
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  0.96305
_exptl_absorpt_correction_T_min  0.86672
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2006)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+10.8805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                2357
_reflns_number_total             2682
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2267.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2216417
_cod_database_fobs_code          2216417
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 0.5000 -0.02872(10) 0.2500 0.0174(3) Uani d S 1
S S2 0.46838(4) 0.23246(7) 0.30370(8) 0.0183(2) Uani d . 1
N N1 0.32997(13) 0.1448(3) 0.5839(3) 0.0188(6) Uani d . 1
O O1 0.39897(11) 0.2266(2) 0.4329(2) 0.0222(5) Uani d . 1
C C1 0.39538(15) 0.1118(3) 0.4513(3) 0.0172(7) Uani d . 1
C C2 0.42747(15) 0.0229(3) 0.3960(3) 0.0161(7) Uani d . 1
C C3 0.42230(15) -0.1102(3) 0.4154(3) 0.0192(7) Uani d . 1
H H3 0.4425 -0.1664 0.3776 0.023 Uiso calc R 1
C C4 0.38870(15) -0.1536(3) 0.4873(3) 0.0190(7) Uani d . 1
H H4 0.3863 -0.2395 0.4988 0.023 Uiso calc R 1
C C5 0.35623(14) -0.0699(3) 0.5473(3) 0.0164(7) Uani d . 1
C C6 0.32260(15) -0.1123(3) 0.6273(3) 0.0209(7) Uani d . 1
H H6 0.3204 -0.1973 0.6437 0.025 Uiso calc R 1
C C7 0.29310(15) -0.0268(3) 0.6809(3) 0.0203(7) Uani d . 1
H H7 0.2703 -0.0539 0.7329 0.024 Uiso calc R 1
C C8 0.29742(15) 0.1021(3) 0.6570(3) 0.0201(7) Uani d . 1
C C9 0.35899(14) 0.0610(3) 0.5305(3) 0.0162(7) Uani d . 1
C C10 0.46249(14) 0.0732(3) 0.3239(3) 0.0160(6) Uani d . 1
C C11 0.26353(17) 0.1970(3) 0.7105(4) 0.0282(8) Uani d . 1
H H11A 0.2813 0.2779 0.7113 0.042 Uiso calc R 1
H H11B 0.2633 0.1734 0.7937 0.042 Uiso calc R 1
H H11C 0.2243 0.2004 0.6606 0.042 Uiso calc R 1
C C12 0.38385(16) 0.4303(3) 0.6259(3) 0.0219(7) Uani d . 1
H H12 0.3788 0.3427 0.5991 0.026 Uiso calc R 1
Cl Cl1 0.32240(4) 0.51737(9) 0.54728(9) 0.0323(3) Uani d . 1
Cl Cl2 0.39044(5) 0.43802(10) 0.78724(8) 0.0365(3) Uani d . 1
Cl Cl3 0.44742(4) 0.49030(9) 0.59141(8) 0.0295(2) Uani d . 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 0 '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 0.006 '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'
Cl Cl 0.1484 0.1585 '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
C10 S1 C10 2_655 . 102.3(2)
C10 S2 S2 . 2_655 99.41(11)
C8 N1 C9 . . 118.4(3)
O1 C1 C2 . . 120.8(3)
O1 C1 C9 . . 122.0(3)
C2 C1 C9 . . 117.2(3)
C10 C2 C1 . . 116.2(3)
C10 C2 C3 . . 123.2(3)
C1 C2 C3 . . 120.6(3)
C4 C3 C2 . . 120.8(3)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 121.6(3)
C3 C4 H4 . . 119.2
C5 C4 H4 . . 119.2
C6 C5 C9 . . 116.9(3)
C6 C5 C4 . . 122.8(3)
C9 C5 C4 . . 120.2(3)
C7 C6 C5 . . 119.3(3)
C7 C6 H6 . . 120.3
C5 C6 H6 . . 120.3
C6 C7 C8 . . 119.9(3)
C6 C7 H7 . . 120.0
C8 C7 H7 . . 120.0
N1 C8 C7 . . 121.9(3)
N1 C8 C11 . . 117.2(3)
C7 C8 C11 . . 120.8(3)
N1 C9 C5 . . 123.5(3)
N1 C9 C1 . . 117.0(3)
C5 C9 C1 . . 119.6(3)
C2 C10 S2 . . 122.2(2)
C2 C10 S1 . . 118.5(2)
S2 C10 S1 . . 119.27(19)
C8 C11 H11A . . 109.5
C8 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C8 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
Cl2 C12 Cl3 . . 109.62(19)
Cl2 C12 Cl1 . . 109.6(2)
Cl3 C12 Cl1 . . 110.34(19)
Cl2 C12 H12 . . 109.1
Cl3 C12 H12 . . 109.1
Cl1 C12 H12 . . 109.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C10 2_655 1.735(3)
S1 C10 . 1.735(3)
S2 C10 . 1.725(3)
S2 S2 2_655 2.1338(16)
N1 C8 . 1.331(4)
N1 C9 . 1.351(4)
O1 C1 . 1.248(4)
C1 C2 . 1.445(5)
C1 C9 . 1.479(5)
C2 C10 . 1.395(5)
C2 C3 . 1.447(4)
C3 C4 . 1.342(5)
C3 H3 . 0.9300
C4 C5 . 1.445(5)
C4 H4 . 0.9300
C5 C6 . 1.406(5)
C5 C9 . 1.414(5)
C6 C7 . 1.371(5)
C6 H6 . 0.9300
C7 C8 . 1.410(5)
C7 H7 . 0.9300
C8 C11 . 1.503(5)
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 Cl2 . 1.763(3)
C12 Cl3 . 1.765(4)
C12 Cl1 . 1.769(4)
C12 H12 . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 S1 0.93 2.64 3.032(3) 106.0
C12 H12 O1 0.98 2.37 3.136(4) 134.7
C12 H12 N1 0.98 2.40 3.294(4) 152.1
