##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1570214'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2,6-Dibenzylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-\
tetrathione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H16 N2 S4'
_chemical_formula_sum     'C24 H16 N2 S4'
_chemical_formula_iupac     'C24 H16 N2 S4'
_chemical_formula_weight     460.63
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.8571(4)
_cell_length_b     4.7724(3)
_cell_length_c     32.0010(17)
_cell_angle_alpha     90
_cell_angle_beta     95.916(4)
_cell_angle_gamma     90
_cell_volume     1041.65(11)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3915
_cell_measurement_theta_min     2.56
_cell_measurement_theta_max     25.54
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.430
_exptl_crystal_size_mid     0.340
_exptl_crystal_size_min     0.010
_exptl_crystal_density_diffrn     1.469
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.471
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.823
_shelx_estimated_absorpt_T_max     0.995
_exptl_absorpt_correction_T_min     0.6459
_exptl_absorpt_correction_T_max     0.7457
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1829
_diffrn_reflns_av_R_equivalents     0.0592
_diffrn_reflns_theta_min     1.279
_diffrn_reflns_theta_max     24.997
_diffrn_reflns_theta_full     24.997
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -6
_diffrn_reflns_limit_l_max     38
_refine_special_details
;
Refined as a 2-component twin
;
_reflns_number_total     1829
_reflns_number_gt     1640
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0440
_refine_ls_R_factor_gt     0.0381
_refine_ls_wR_factor_gt     0.0862
_refine_ls_wR_factor_ref     0.0885
_refine_ls_goodness_of_fit_ref     1.046
_refine_ls_restrained_S_all     1.046
_refine_ls_number_reflns     1829
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0370P)²+0.6197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.261
_refine_diff_density_min     -0.233
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.50612(10) 0.30438(16) 0.05735(2) 0.0259(2) Uani d 1 . .
    S S2 1.10897(11) 0.99091(17) 0.10558(2) 0.0299(2) Uani d 1 . .
    N N1 0.7913(3) 0.6607(5) 0.08677(6) 0.0192(5) Uani d 1 . .
    C C1 0.7132(4) 0.4707(6) 0.05665(7) 0.0189(6) Uani d 1 . .
    C C2 0.9678(4) 0.7718(6) 0.07722(7) 0.0199(6) Uani d 1 . .
    C C3 1.0046(4) 0.6467(6) 0.03656(7) 0.0182(6) Uani d 1 . .
    C C4 0.8521(4) 0.4592(6) 0.02468(7) 0.0184(6) Uani d 1 . .
    C C5 1.1572(4) 0.6945(6) 0.01231(7) 0.0199(6) Uani d 1 . .
    H H5 1.2604 0.8225 0.0204 0.024 Uiso calc 1 . .
    C C6 0.6888(4) 0.7471(6) 0.12291(8) 0.0232(6) Uani d 1 . .
    H H6A 0.5503 0.7888 0.1130 0.028 Uiso calc 1 . .
    H H6B 0.7493 0.9218 0.1348 0.028 Uiso calc 1 . .
    C C7 0.6944(4) 0.5277(6) 0.15724(8) 0.0235(6) Uani d 1 . .
    C C8 0.5208(5) 0.4058(6) 0.16745(9) 0.0300(7) Uani d 1 . .
    H H8 0.3993 0.4576 0.1525 0.036 Uiso calc 1 . .
    C C9 0.5252(5) 0.2086(7) 0.19950(10) 0.0411(9) Uani d 1 . .
    H H9 0.4069 0.1252 0.2064 0.049 Uiso calc 1 . .
    C C10 0.7023(5) 0.1345(7) 0.22125(9) 0.0423(9) Uani d 1 . .
    H H10 0.7052 0.0004 0.2433 0.051 Uiso calc 1 . .
    C C11 0.8741(5) 0.2531(7) 0.21127(9) 0.0383(8) Uani d 1 . .
    H H11 0.9952 0.2000 0.2263 0.046 Uiso calc 1 . .
    C C12 0.8711(4) 0.4503(6) 0.17935(8) 0.0289(7) Uani d 1 . .
    H H12 0.9901 0.5326 0.1726 0.035 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.629(3) ?
    S2 C2 . 1.635(3) ?
    N1 C2 . 1.384(3) ?
    N1 C1 . 1.390(3) ?
    N1 C6 . 1.473(3) ?
    C1 C4 . 1.469(3) ?
    C2 C3 . 1.477(3) ?
    C3 C5 . 1.384(4) ?
    C3 C4 . 1.399(4) ?
    C4 C5 3_765 1.388(3) ?
    C5 C4 3_765 1.388(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.515(4) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C12 . 1.388(4) ?
    C7 C8 . 1.394(4) ?
    C8 C9 . 1.390(4) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.382(5) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.374(5) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.388(4) ?
    C11 H11 . 0.9500 ?
    C12 H12 . 0.9500 ?
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 N1 C1 . . 112.3(2) ?
    C2 N1 C6 . . 124.4(2) ?
    C1 N1 C6 . . 123.1(2) ?
    N1 C1 C4 . . 106.0(2) ?
    N1 C1 S1 . . 125.63(19) ?
    C4 C1 S1 . . 128.3(2) ?
    N1 C2 C3 . . 105.8(2) ?
    N1 C2 S2 . . 127.14(19) ?
    C3 C2 S2 . . 127.06(19) ?
    C5 C3 C4 . . 122.7(2) ?
    C5 C3 C2 . . 129.4(2) ?
    C4 C3 C2 . . 107.9(2) ?
    C5 C4 C3 3_765 . 122.5(2) ?
    C5 C4 C1 3_765 . 129.6(2) ?
    C3 C4 C1 . . 107.9(2) ?
    C3 C5 C4 . 3_765 114.8(2) ?
    C3 C5 H5 . . 122.6 ?
    C4 C5 H5 3_765 . 122.6 ?
    N1 C6 C7 . . 113.4(2) ?
    N1 C6 H6A . . 108.9 ?
    C7 C6 H6A . . 108.9 ?
    N1 C6 H6B . . 108.9 ?
    C7 C6 H6B . . 108.9 ?
    H6A C6 H6B . . 107.7 ?
    C12 C7 C8 . . 119.4(3) ?
    C12 C7 C6 . . 120.6(2) ?
    C8 C7 C6 . . 120.0(2) ?
    C9 C8 C7 . . 120.1(3) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C10 C9 C8 . . 119.7(3) ?
    C10 C9 H9 . . 120.1 ?
    C8 C9 H9 . . 120.1 ?
    C11 C10 C9 . . 120.5(3) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C10 C11 C12 . . 120.2(3) ?
    C10 C11 H11 . . 119.9 ?
    C12 C11 H11 . . 119.9 ?
    C11 C12 C7 . . 120.1(3) ?
    C11 C12 H12 . . 119.9 ?
    C7 C12 H12 . . 119.9 ?
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
    C2 N1 C1 C4 . . . . -0.2(3) ?
    C6 N1 C1 C4 . . . . 175.6(2) ?
    C2 N1 C1 S1 . . . . -178.89(19) ?
    C6 N1 C1 S1 . . . . -3.1(3) ?
    C1 N1 C2 C3 . . . . 1.5(3) ?
    C6 N1 C2 C3 . . . . -174.3(2) ?
    C1 N1 C2 S2 . . . . -177.3(2) ?
    C6 N1 C2 S2 . . . . 7.0(4) ?
    N1 C2 C3 C5 . . . . 177.5(3) ?
    S2 C2 C3 C5 . . . . -3.8(4) ?
    N1 C2 C3 C4 . . . . -2.2(3) ?
    S2 C2 C3 C4 . . . . 176.5(2) ?
    C5 C3 C4 C5 . . . 3_765 0.3(4) ?
    C2 C3 C4 C5 . . . 3_765 -180.0(2) ?
    C5 C3 C4 C1 . . . . -177.6(2) ?
    C2 C3 C4 C1 . . . . 2.1(3) ?
    N1 C1 C4 C5 . . . 3_765 -179.0(3) ?
    S1 C1 C4 C5 . . . 3_765 -0.3(4) ?
    N1 C1 C4 C3 . . . . -1.2(3) ?
    S1 C1 C4 C3 . . . . 177.4(2) ?
    C4 C3 C5 C4 . . . 3_765 -0.3(4) ?
    C2 C3 C5 C4 . . . 3_765 -180.0(2) ?
    C2 N1 C6 C7 . . . . -108.7(3) ?
    C1 N1 C6 C7 . . . . 76.0(3) ?
    N1 C6 C7 C12 . . . . 64.7(3) ?
    N1 C6 C7 C8 . . . . -116.7(3) ?
    C12 C7 C8 C9 . . . . 0.0(4) ?
    C6 C7 C8 C9 . . . . -178.7(3) ?
    C7 C8 C9 C10 . . . . 0.1(5) ?
    C8 C9 C10 C11 . . . . -0.3(5) ?
    C9 C10 C11 C12 . . . . 0.4(5) ?
    C10 C11 C12 C7 . . . . -0.3(5) ?
    C8 C7 C12 C11 . . . . 0.1(4) ?
    C6 C7 C12 C11 . . . . 178.8(3) ?
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
    C6 H6B S2 . 0.99 2.75 3.208(3) 109.0
    C6 H6B Cg1 1_565 0.99 2.66 3.498(3) 142.0
data_New_Global_Publ_Block
_journal_date_recd_electronic     2017-08-14
_journal_date_accepted     2017-08-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      9
_journal_page_first     1379
_journal_page_last     1381
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017012154
_journal_coeditor_code     HG5493
_publ_contact_author_name     'Woo, Chang Hwa'
_publ_contact_author_address
;
Director of Planning Center
Gyeongsang National University Academy and Industry Collaboration
501 Jinjudaero
Jinjusi 52828
Republic of Korea
;
_publ_contact_author_email     woo@gnu.ac.kr
_publ_contact_author_fax     '+82-55-772-2789'
_publ_contact_author_phone     '+82-55-772-2789'
_publ_section_title
;\
Crystal structure of
2,6-dibenzylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-\
tetrathione
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Im, Hansu' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences
Gyeongsang National University
Jinju 52828
Republic of Korea
;
    'Park, Hyunjin' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences
Gyeongsang National University
Jinju 52828
Republic of Korea
;
    'Kim, Tae Ho' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences
Gyeongsang National University
Jinju 52828
Republic of Korea
;
    'Woo, Chang Hwa' .
;
Director of Planning Center
Gyeongsang National University Academy and Industry Collaboration
501 Jinjudaero
Jinjusi 52828
Republic of Korea
;
_publ_section_synopsis
;
The title compound comprises a central pyromellitic diimide substituted with S
atoms and terminal benzyl groups. In the crystal, adjacent molecules are
linked by C---H...π interactions and short S...S contacts, forming a
two-dimensional network parellel to the (110) plane.
;
