#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017980.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_2017980
loop_
_publ_author_name
'Zuluaga, Fabio'
'Grande, Carlos'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 1,4-Phenylenebis(methylene) bis(9H-carbazole-9-carbodithioate)
;
_journal_coeditor_code           GG3251
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o77
_journal_page_last               o79
_journal_paper_doi               10.1107/S0108270110053102
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C34 H24 N2 S4'
_chemical_formula_moiety         'C34 H24 N2 S4'
_chemical_formula_sum            'C34 H24 N2 S4'
_chemical_formula_weight         588.83
_chemical_name_systematic
;
1,4-Phenylenebis(methylene) bis(9H-carbazole-9-carbodithioate)
;
_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                 96.646(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.296(2)
_cell_length_b                   10.0793(19)
_cell_length_c                   13.137(2)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.67
_cell_volume                     1354.2(4)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al., 2000)'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15566
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0292P)²+1.0522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                1880
_reflns_number_total             2520
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3251.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017980
_cod_database_fobs_code          2017980
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0071(3) 0.8142(3) 0.3388(2) 0.0286(7) Uani d . 1 . .
H H1 0.0756 0.7533 0.3308 0.034 Uiso calc R 1 . .
C C2 -0.1208(3) 0.7738(3) 0.3284(2) 0.0358(8) Uani d . 1 . .
H H2 -0.1412 0.6835 0.3136 0.043 Uiso calc R 1 . .
C C3 -0.2211(3) 0.8627(4) 0.3392(2) 0.0407(8) Uani d . 1 . .
H H3 -0.3089 0.8319 0.3335 0.049 Uiso calc R 1 . .
C C4 -0.1952(3) 0.9937(3) 0.3579(2) 0.0363(8) Uani d . 1 . .
H H4 -0.2644 1.0545 0.3636 0.044 Uiso calc R 1 . .
C C4A -0.0674(3) 1.0365(3) 0.36824(19) 0.0284(7) Uani d . 1 . .
C C4B -0.0104(3) 1.1665(3) 0.37977(19) 0.0302(7) Uani d . 1 . .
C C5 -0.0658(3) 1.2915(3) 0.3878(2) 0.0391(8) Uani d . 1 . .
H H5 -0.1578 1.3013 0.3862 0.047 Uiso calc R 1 . .
C C6 0.0135(4) 1.3989(3) 0.3980(2) 0.0482(10) Uani d . 1 . .
H H6 -0.0235 1.4847 0.4029 0.058 Uiso calc R 1 . .
C C7 0.1470(4) 1.3856(3) 0.4014(2) 0.0456(9) Uani d . 1 . .
H H7 0.2006 1.4624 0.4110 0.055 Uiso calc R 1 . .
C C8 0.2047(3) 1.2638(3) 0.3912(2) 0.0369(8) Uani d . 1 . .
H H8 0.2967 1.2555 0.3921 0.044 Uiso calc R 1 . .
C C8A 0.1239(3) 1.1541(3) 0.37956(19) 0.0281(7) Uani d . 1 . .
N N9 0.1537(2) 1.0175(2) 0.37045(16) 0.0248(5) Uani d . 1 . .
C C9A 0.0337(3) 0.9463(3) 0.36135(19) 0.0248(6) Uani d . 1 . .
C C10 0.2786(3) 0.9660(3) 0.37496(19) 0.0250(6) Uani d . 1 . .
S S10 0.40383(8) 1.04443(8) 0.33861(6) 0.0349(2) Uani d . 1 . .
S S11 0.29150(7) 0.80717(7) 0.42721(6) 0.0298(2) Uani d . 1 . .
C C11 0.4588(3) 0.7648(3) 0.4178(2) 0.0263(6) Uani d . 1 . .
H H11A 0.4767 0.7671 0.3454 0.032 Uiso calc R 1 . .
H H11B 0.5180 0.8285 0.4574 0.032 Uiso calc R 1 . .
C C21 0.4797(3) 0.6278(3) 0.46062(19) 0.0225(6) Uani d . 1 . .
C C22 0.5133(3) 0.5255(3) 0.3993(2) 0.0278(7) Uani d . 1 . .
H H22 0.5227 0.5423 0.3294 0.033 Uiso calc R 1 . .
C C23 0.5334(3) 0.3994(3) 0.4378(2) 0.0276(7) Uani d . 1 . .
H H23 0.5566 0.3302 0.3943 0.033 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'
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
C2 C1 C9A . . 118.1(3) ?
C2 C1 H1 . . 121.0 ?
C9A C1 H1 . . 121.0 ?
C1 C2 C3 . . 121.1(3) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C4A . . 119.1(3) ?
C3 C4 H4 . . 120.5 ?
C4A C4 H4 . . 120.5 ?
C4 C4A C9A . . 120.1(3) ?
C4 C4A C4B . . 132.1(3) ?
C9A C4A C4B . . 107.6(3) ?
C8A C4B C5 . . 119.9(3) ?
C8A C4B C4A . . 108.2(3) ?
C5 C4B C4A . . 131.9(3) ?
C6 C5 C4B . . 118.9(3) ?
C6 C5 H5 . . 120.5 ?
C4B C5 H5 . . 120.5 ?
C5 C6 C7 . . 121.0(3) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C6 C7 C8 . . 121.6(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C7 C8 C8A . . 117.6(3) ?
C7 C8 H8 . . 121.2 ?
C8A C8 H8 . . 121.2 ?
C8 C8A C4B . . 120.9(3) ?
C8 C8A N9 . . 130.8(3) ?
C4B C8A N9 . . 108.3(3) ?
C10 N9 C8A . . 124.8(2) ?
C10 N9 C9A . . 127.6(2) ?
C8A N9 C9A . . 107.6(2) ?
C1 C9A C4A . . 120.7(3) ?
C1 C9A N9 . . 130.7(3) ?
C4A C9A N9 . . 108.3(2) ?
N9 C10 S10 . . 124.7(2) ?
N9 C10 S11 . . 112.99(19) ?
S10 C10 S11 . . 122.32(17) ?
C10 S11 C11 . . 102.82(13) ?
C21 C11 S11 . . 106.91(19) ?
C21 C11 H11A . . 110.3 ?
S11 C11 H11A . . 110.3 ?
C21 C11 H11B . . 110.3 ?
S11 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.6 ?
C22 C21 C23 . 3_666 118.3(3) ?
C22 C21 C11 . . 120.4(2) ?
C23 C21 C11 3_666 . 121.3(2) ?
C23 C22 C21 . . 121.0(2) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C22 C23 C21 . 3_666 120.7(3) ?
C22 C23 H23 . . 119.6 ?
C21 C23 H23 3_666 . 119.6 ?
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
C1 C2 . 1.371(4) y
C2 C3 . 1.386(4) y
C3 C4 . 1.364(5) y
C4 C4A . 1.377(4) y
C4A C4B . 1.437(4) y
C4B C5 . 1.392(4) y
C5 C6 . 1.353(5) y
C6 C7 . 1.376(5) y
C7 C8 . 1.378(4) y
C8 C8A . 1.382(4) y
C8A N9 . 1.419(3) y
N9 C9A . 1.422(3) y
C9A C1 . 1.384(4) y
C4A C9A . 1.393(4) y
C4B C8A . 1.389(4) y
C1 H1 . 0.9500 ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
N9 C10 . 1.381(3) y
C10 S10 . 1.630(3) y
C10 S11 . 1.741(3) y
S11 C11 . 1.793(3) y
C11 C21 . 1.497(4) y
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C21 C22 . 1.377(4) ?
C21 C23 3_666 1.384(4) ?
C22 C23 . 1.375(4) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
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
C22 H22 Cg 2_545 0.95 2.89 3.666(3) 140 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9A C1 C2 C3 . . . . 0.6(4) ?
C1 C2 C3 C4 . . . . 1.7(4) ?
C2 C3 C4 C4A . . . . -1.4(4) ?
C3 C4 C4A C9A . . . . -1.0(4) ?
C3 C4 C4A C4B . . . . 174.3(3) ?
C4 C4A C4B C8A . . . . -175.7(3) ?
C9A C4A C4B C8A . . . . 0.1(3) ?
C4 C4A C4B C5 . . . . 2.6(5) ?
C9A C4A C4B C5 . . . . 178.5(3) ?
C8A C4B C5 C6 . . . . -1.7(4) ?
C4A C4B C5 C6 . . . . -179.9(3) ?
C4B C5 C6 C7 . . . . -0.6(5) ?
C5 C6 C7 C8 . . . . 2.2(5) ?
C6 C7 C8 C8A . . . . -1.4(5) ?
C7 C8 C8A C4B . . . . -1.0(4) ?
C7 C8 C8A N9 . . . . -177.9(3) ?
C5 C4B C8A C8 . . . . 2.5(4) ?
C4A C4B C8A C8 . . . . -178.9(2) ?
C5 C4B C8A N9 . . . . -179.9(2) ?
C4A C4B C8A N9 . . . . -1.3(3) ?
C8 C8A N9 C10 . . . . 2.1(4) ?
C4B C8A N9 C10 . . . . -175.1(2) ?
C8 C8A N9 C9A . . . . 179.3(3) ?
C4B C8A N9 C9A . . . . 2.0(3) ?
C2 C1 C9A C4A . . . . -3.1(4) ?
C2 C1 C9A N9 . . . . -175.8(3) ?
C4 C4A C9A C1 . . . . 3.4(4) ?
C4B C4A C9A C1 . . . . -173.1(2) ?
C4 C4A C9A N9 . . . . 177.6(2) ?
C4B C4A C9A N9 . . . . 1.2(3) ?
C10 N9 C9A C1 . . . . -11.5(4) ?
C8A N9 C9A C1 . . . . 171.5(3) ?
C10 N9 C9A C4A . . . . 175.1(2) ?
C8A N9 C9A C4A . . . . -2.0(3) ?
C8A N9 C10 S10 . . . . -30.1(4) ?
C9A N9 C10 S10 . . . . 153.3(2) ?
C8A N9 C10 S11 . . . . 148.4(2) ?
C9A N9 C10 S11 . . . . -28.2(3) y
N9 C10 S11 C11 . . . . 177.53(19) y
S10 C10 S11 C11 . . . . -3.9(2) ?
C10 S11 C11 C21 . . . . -179.58(18) y
S11 C11 C21 C22 . . . . 117.4(3) y
S11 C11 C21 C23 . . . 3_666 -63.0(3) ?
C23 C21 C22 C23 3_666 . . . 0.0(5) ?
C11 C21 C22 C23 . . . . 179.6(3) ?
C21 C22 C23 C21 . . . 3_666 0.0(5) ?
