##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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                 #
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# This file may be used for bona fide research purposes within the           #
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data_DITCAQ
_audit_creation_method     SHELXL-2014/6
_journal_date_recd_electronic     2016-07-26
_journal_date_accepted     2016-10-14
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue     12
_journal_page_first     923
_journal_page_last     931
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229616016387
_journal_coeditor_code     YO3023
_publ_contact_author_name     'Danielle L. Gray'
_publ_contact_author_address
;
School of Chemical Sciences
University of Illinois at Urbana-Champaign
505 S Mathews Ave, Box 59-1
Urbana
IL 61801
USA
;
_publ_contact_author_email     dgray@illinois.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '217-244-1708'
_publ_section_title
;
Synthesis and structures of
11,11,12,12-tetracyano-2,6-diiodo-9,10-anthraquinodimethane and its 2:1
cocrystals with anthracene, pyrene and tetrathiafulvalene
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ren, Yi' .
;
Department of Chemistry
University of Illinois at Urbana--Champaign
600 S. Mathews Ave
Urbana
IL 61801
USA
;
    'Lee, Semin' .
;
Beckman Institute for Advanced Science and Technology
University of Illinois at Urbana--Champaign
405 N. Mathews Ave.
Urbana
IL 61801
USA
;
    'Bertke, Jeffery' .
;
Department of Chemistry
Georgetown University
146 Regents Hall
Washington
DC 20057
USA
;
    'Gray, Danielle L.' .
;
School of Chemical Sciences
University of Illinois at Urbana--Champaign
505 S. Mathews Ave
Box 59-1
Urbana
IL 61801
USA
;
    'Moore, Jeffrey S.' .
;
Department of Chemistry
University of Illinois at Urbana-Champaign
600 S. Mathews Ave
Urbana
IL 61801
USA
Beckman Institute for Advanced Science and Technology
University of Illinois at Urbana--Champaign
405 N. Mathews Ave.
Urbana
IL 61801
USA
;
_publ_section_synopsis
;
In the structures of
11,11,12,12-tetracyano-2,6-diiodo-9,10-anthraquinodimethane (DITCAQ) and its
2:1 cocrystals with tetrathiafulvalene, pyrene and anthracene, the
saddle-shaped DITCAQ molecule radually transforms into a less bent geometry as
the charge-transfer interactions between DITCAQ and the electron donors
enhances.
;
_database_code_depnum_ccdc_archive     'CCDC 1509825'
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H6 I2 N4'
_chemical_formula_sum     'C20 H6 I2 N4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H6 I2 N4'
_chemical_formula_weight     556.09
_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     orthorhombic
_space_group_name_H-M_alt     'P n a 21'
_space_group_name_Hall     'P 2c -2n'
loop_
    _space_group_symop_operation_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'
_cell_length_a     8.7660(3)
_cell_length_b     12.2655(4)
_cell_length_c     16.4903(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1773.03(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9591
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     27.11
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.224
_exptl_crystal_size_mid     0.189
_exptl_crystal_size_min     0.099
_exptl_crystal_density_diffrn     2.083
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1040
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0.00 -1.00 -1.00 0.0260
    0.00 0.00 1.00 0.0520
    0.00 1.00 -1.00 0.0430
    -1.00 0.00 0.00 0.1040
    1.00 0.00 0.00 0.1120
    1.00 1.00 2.00 0.0680
    0.00 -1.00 0.00 0.0420
    0.00 -1.00 2.00 0.0450
_exptl_absorpt_coefficient_mu     3.558
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.503
_shelx_estimated_absorpt_T_max     0.720
_exptl_absorpt_correction_T_min     0.99892
_exptl_absorpt_correction_T_max     0.99957
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Five frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2013) then corrected for absorption by integration using
SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale
the combined data. No decay correction was applied.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'microfocus sealed tube'
_diffrn_radiation_monochromator     'multilayer mirrors'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20684
_diffrn_reflns_av_R_equivalents     0.0323
_diffrn_reflns_theta_min     2.470
_diffrn_reflns_theta_max     27.153
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions
suggested the unambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The final map had no significant features. A final analysis of
variance between observed and calculated structure factors showed little
dependence on amplitude and resolution.
;
_reflns_number_total     3929
_reflns_number_gt     3849
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0197
_refine_ls_R_factor_gt     0.0189
_refine_ls_wR_factor_gt     0.0447
_refine_ls_wR_factor_ref     0.0450
_refine_ls_goodness_of_fit_ref     1.167
_refine_ls_restrained_S_all     1.167
_refine_ls_number_reflns     3929
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0230P)²+0.2251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.321
_refine_diff_density_min     -0.815
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack (1983), with 1893 Friedel pairs
;
_refine_ls_abs_structure_Flack     -0.016(11)
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'
    'I' 'I' -0.4742 1.8119
                         '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
;
XPREP (Bruker, 2014) and SADABS (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_publication_material
;
XCIF (Bruker, 2014)
;
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
    I I1 0.61913(3) 0.27014(2) 0.38906(2) 0.01539(7) Uani d 1 . .
    I I2 0.42334(4) 1.10665(2) 0.58154(2) 0.01841(8) Uani d 1 . .
    N N1 0.2046(5) 0.4920(3) 0.7375(3) 0.0237(10) Uani d 1 . .
    N N2 0.0777(5) 0.8249(3) 0.7036(3) 0.0165(8) Uani d 1 . .
    N N3 0.1475(5) 0.4509(3) 0.2769(3) 0.0169(8) Uani d 1 . .
    N N4 0.0564(5) 0.7875(3) 0.2597(3) 0.0189(9) Uani d 1 . .
    C C1 0.5113(5) 0.3973(3) 0.4514(3) 0.0115(8) Uani d 1 . .
    C C2 0.5116(5) 0.3992(3) 0.5355(3) 0.0129(9) Uani d 1 . .
    H H2 0.5578 0.3412 0.5648 0.016 Uiso calc 1 . .
    C C3 0.4448(4) 0.4851(3) 0.5772(4) 0.0118(8) Uani d 1 . .
    H H3 0.4473 0.4865 0.6348 0.014 Uiso calc 1 . .
    C C4 0.3742(5) 0.5694(4) 0.5348(3) 0.0102(8) Uani d 1 . .
    C C5 0.3056(5) 0.6652(3) 0.5746(3) 0.0089(7) Uani d 1 . .
    C C6 0.3227(5) 0.7678(3) 0.5289(3) 0.0094(8) Uani d 1 . .
    C C7 0.3530(5) 0.8668(3) 0.5683(3) 0.0104(8) Uani d 1 . .
    H H7 0.3606 0.8696 0.6257 0.013 Uiso calc 1 . .
    C C8 0.3719(5) 0.9610(3) 0.5220(3) 0.0115(8) Uani d 1 . .
    C C9 0.3597(5) 0.9587(4) 0.4374(3) 0.0125(9) Uani d 1 . .
    H H9 0.3714 1.0236 0.4066 0.015 Uiso calc 1 . .
    C C10 0.3301(5) 0.8601(3) 0.3991(3) 0.0109(8) Uani d 1 . .
    H H10 0.3208 0.8580 0.3417 0.013 Uiso calc 1 . .
    C C11 0.3139(5) 0.7638(3) 0.4439(3) 0.0100(8) Uani d 1 . .
    C C12 0.2931(5) 0.6562(3) 0.4056(2) 0.0100(9) Uani d 1 . .
    C C13 0.3704(5) 0.5654(3) 0.4487(3) 0.0104(8) Uani d 1 . .
    C C14 0.4406(5) 0.4798(3) 0.4077(3) 0.0117(9) Uani d 1 . .
    H H14 0.4401 0.4779 0.3501 0.014 Uiso calc 1 . .
    C C15 0.2304(5) 0.6617(4) 0.6468(3) 0.0108(8) Uani d 1 . .
    C C16 0.2175(5) 0.5652(4) 0.6960(3) 0.0144(9) Uani d 1 . .
    C C17 0.1492(5) 0.7539(3) 0.6787(3) 0.0109(9) Uani d 1 . .
    C C18 0.2083(5) 0.6402(3) 0.3378(3) 0.0111(8) Uani d 1 . .
    C C19 0.1785(5) 0.5331(3) 0.3045(3) 0.0124(9) Uani d 1 . .
    C C20 0.1273(5) 0.7251(4) 0.2954(3) 0.0128(9) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    I1 C1 . 2.094(4) ?
    I2 C8 . 2.089(4) ?
    N1 C16 . 1.135(6) ?
    N2 C17 . 1.148(6) ?
    N3 C19 . 1.139(6) ?
    N4 C20 . 1.148(6) ?
    C1 C2 . 1.386(6) ?
    C1 C14 . 1.389(6) ?
    C2 C3 . 1.388(6) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.393(6) ?
    C3 H3 . 0.9500 ?
    C4 C13 . 1.420(6) ?
    C4 C5 . 1.475(6) ?
    C5 C15 . 1.361(6) ?
    C5 C6 . 1.475(5) ?
    C6 C7 . 1.402(6) ?
    C6 C11 . 1.405(6) ?
    C7 C8 . 1.395(6) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.399(6) ?
    C9 C10 . 1.388(6) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.402(6) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.473(6) ?
    C12 C18 . 1.357(6) ?
    C12 C13 . 1.485(6) ?
    C13 C14 . 1.393(6) ?
    C14 H14 . 0.9500 ?
    C15 C17 . 1.437(6) ?
    C15 C16 . 1.439(6) ?
    C18 C20 . 1.442(6) ?
    C18 C19 . 1.448(6) ?
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 C14 . . 120.5(4) ?
    C2 C1 I1 . . 120.2(3) ?
    C14 C1 I1 . . 119.3(3) ?
    C1 C2 C3 . . 120.5(4) ?
    C1 C2 H2 . . 119.7 ?
    C3 C2 H2 . . 119.7 ?
    C2 C3 C4 . . 120.1(5) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    C3 C4 C13 . . 119.2(4) ?
    C3 C4 C5 . . 123.2(4) ?
    C13 C4 C5 . . 117.6(4) ?
    C15 C5 C4 . . 124.2(4) ?
    C15 C5 C6 . . 121.5(4) ?
    C4 C5 C6 . . 114.3(4) ?
    C7 C6 C11 . . 120.2(4) ?
    C7 C6 C5 . . 121.4(4) ?
    C11 C6 C5 . . 118.3(4) ?
    C8 C7 C6 . . 119.1(4) ?
    C8 C7 H7 . . 120.5 ?
    C6 C7 H7 . . 120.5 ?
    C7 C8 C9 . . 121.4(4) ?
    C7 C8 I2 . . 118.5(3) ?
    C9 C8 I2 . . 120.2(3) ?
    C10 C9 C8 . . 119.0(4) ?
    C10 C9 H9 . . 120.5 ?
    C8 C9 H9 . . 120.5 ?
    C9 C10 C11 . . 120.9(4) ?
    C9 C10 H10 . . 119.6 ?
    C11 C10 H10 . . 119.6 ?
    C10 C11 C6 . . 119.4(4) ?
    C10 C11 C12 . . 122.8(4) ?
    C6 C11 C12 . . 117.8(4) ?
    C18 C12 C11 . . 123.4(4) ?
    C18 C12 C13 . . 122.4(4) ?
    C11 C12 C13 . . 114.2(4) ?
    C14 C13 C4 . . 120.1(4) ?
    C14 C13 C12 . . 122.3(4) ?
    C4 C13 C12 . . 117.6(4) ?
    C1 C14 C13 . . 119.6(4) ?
    C1 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C5 C15 C17 . . 122.4(4) ?
    C5 C15 C16 . . 123.8(4) ?
    C17 C15 C16 . . 113.7(4) ?
    N1 C16 C15 . . 176.9(5) ?
    N2 C17 C15 . . 176.6(5) ?
    C12 C18 C20 . . 124.4(4) ?
    C12 C18 C19 . . 122.9(4) ?
    C20 C18 C19 . . 112.5(4) ?
    N3 C19 C18 . . 176.3(5) ?
    N4 C20 C18 . . 175.5(5) ?
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
    C14 C1 C2 C3 . . . . -1.8(7) ?
    I1 C1 C2 C3 . . . . 177.8(3) ?
    C1 C2 C3 C4 . . . . 1.3(7) ?
    C2 C3 C4 C13 . . . . 0.6(6) ?
    C2 C3 C4 C5 . . . . -177.8(4) ?
    C3 C4 C5 C15 . . . . -36.5(7) ?
    C13 C4 C5 C15 . . . . 145.1(4) ?
    C3 C4 C5 C6 . . . . 144.3(4) ?
    C13 C4 C5 C6 . . . . -34.0(6) ?
    C15 C5 C6 C7 . . . . 39.8(6) ?
    C4 C5 C6 C7 . . . . -141.0(4) ?
    C15 C5 C6 C11 . . . . -142.7(5) ?
    C4 C5 C6 C11 . . . . 36.5(6) ?
    C11 C6 C7 C8 . . . . 1.0(7) ?
    C5 C6 C7 C8 . . . . 178.4(4) ?
    C6 C7 C8 C9 . . . . 0.6(7) ?
    C6 C7 C8 I2 . . . . -178.2(3) ?
    C7 C8 C9 C10 . . . . -0.9(7) ?
    I2 C8 C9 C10 . . . . 178.0(3) ?
    C8 C9 C10 C11 . . . . -0.5(7) ?
    C9 C10 C11 C6 . . . . 2.1(7) ?
    C9 C10 C11 C12 . . . . -175.7(4) ?
    C7 C6 C11 C10 . . . . -2.3(7) ?
    C5 C6 C11 C10 . . . . -179.9(4) ?
    C7 C6 C11 C12 . . . . 175.6(4) ?
    C5 C6 C11 C12 . . . . -1.9(6) ?
    C10 C11 C12 C18 . . . . -37.7(7) ?
    C6 C11 C12 C18 . . . . 144.4(4) ?
    C10 C11 C12 C13 . . . . 143.6(4) ?
    C6 C11 C12 C13 . . . . -34.3(6) ?
    C3 C4 C13 C14 . . . . -1.9(6) ?
    C5 C4 C13 C14 . . . . 176.6(4) ?
    C3 C4 C13 C12 . . . . 179.5(4) ?
    C5 C4 C13 C12 . . . . -2.0(6) ?
    C18 C12 C13 C14 . . . . 39.1(6) ?
    C11 C12 C13 C14 . . . . -142.2(4) ?
    C18 C12 C13 C4 . . . . -142.4(4) ?
    C11 C12 C13 C4 . . . . 36.3(5) ?
    C2 C1 C14 C13 . . . . 0.5(7) ?
    I1 C1 C14 C13 . . . . -179.2(3) ?
    C4 C13 C14 C1 . . . . 1.4(6) ?
    C12 C13 C14 C1 . . . . 179.9(4) ?
    C4 C5 C15 C17 . . . . -172.1(4) ?
    C6 C5 C15 C17 . . . . 6.9(7) ?
    C4 C5 C15 C16 . . . . 4.4(7) ?
    C6 C5 C15 C16 . . . . -176.5(4) ?
    C11 C12 C18 C20 . . . . -0.6(7) ?
    C13 C12 C18 C20 . . . . 178.0(4) ?
    C11 C12 C18 C19 . . . . -174.8(4) ?
    C13 C12 C18 C19 . . . . 3.7(6) ?
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
    C2 H2 I2 1_545 0.95 3.12 3.748(4) 125.0
    C7 H7 N3 4 0.95 2.69 3.592(6) 159.6
_shelxl_version_number     2014/6
data_I
_audit_creation_method     'SHELXL-2014/7'
_database_code_depnum_ccdc_archive     'CCDC 1509826'
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane--anthracene (2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H6 I2 N4, 0.5(C14 H10)'
_chemical_formula_sum     'C27 H11 I2 N4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H6 I2 N4, 0.5(C14 H10)'
_chemical_formula_weight     645.20
_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/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_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'
_cell_length_a     13.7727(9)
_cell_length_b     8.5843(5)
_cell_length_c     20.5752(13)
_cell_angle_alpha     90
_cell_angle_beta     105.115(3)
_cell_angle_gamma     90
_cell_volume     2348.4(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8277
_cell_measurement_theta_min     2.58
_cell_measurement_theta_max     27.16
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.213
_exptl_crystal_size_min     0.081
_exptl_crystal_density_diffrn     1.825
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1228
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1.00 0.00 0.00 0.0400
    -1.00 0.00 0.00 0.1000
    0.00 1.00 0.00 0.1100
    0.00 -1.00 0.00 0.0870
    0.00 0.00 1.00 0.0100
    0.00 0.00 -1.00 0.0400
_exptl_absorpt_coefficient_mu     2.701
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.588
_shelx_estimated_absorpt_T_max     0.811
_exptl_absorpt_correction_T_min     0.68128
_exptl_absorpt_correction_T_max     0.87935
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Four frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2013) then corrected for absorption by integration using
SADABS v2014/2 (Bruker, 2014). No decay correction was applied.
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'profile data from ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21378
_diffrn_reflns_av_R_equivalents     0.0404
_diffrn_reflns_theta_min     2.824
_diffrn_reflns_theta_max     27.166
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions
suggested the unambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The highest peaks in the final difference Fourier map were in the
vicinity of atoms I2 and I1; the final map had no other significant features.
A final analysis of variance between observed and calculated structure factors
showed little dependence on amplitude or resolution.
;
_reflns_number_total     5201
_reflns_number_gt     4344
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0357
_refine_ls_R_factor_gt     0.0277
_refine_ls_wR_factor_gt     0.0687
_refine_ls_wR_factor_ref     0.0734
_refine_ls_goodness_of_fit_ref     1.047
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     5201
_refine_ls_number_parameters     362
_refine_ls_number_restraints     198
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0255P)²+1.9565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.874
_refine_diff_density_min     -0.916
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details     ?
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'
    'I' 'I' -0.4742 1.8119
                         '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
;
XPREP (Bruker, 2014) and SADABS (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_publication_material
;
XCIF (Bruker, 2014)
;
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
    I I1 0.80023(2) -0.06182(2) 0.27495(2) 0.04243(7) Uani d 1 . .
    I I2 0.88708(2) -0.07183(3) 0.81408(2) 0.05564(8) Uani d 1 . .
    N N1 0.4533(2) -0.2878(4) 0.46726(16) 0.0570(8) Uani d 1 . .
    N N2 0.5193(2) -0.0972(4) 0.66344(16) 0.0587(8) Uani d 1 . .
    N N3 0.6795(2) 0.4264(3) 0.37357(14) 0.0514(7) Uani d 1 . .
    N N4 0.7651(2) 0.5770(3) 0.57558(14) 0.0457(6) Uani d 1 . .
    C C1 0.7533(2) -0.0610(3) 0.36362(14) 0.0319(6) Uani d 1 . .
    C C2 0.7029(2) -0.1914(3) 0.37856(14) 0.0358(6) Uani d 1 . .
    H H2A 0.6886 -0.2744 0.3486 0.043 Uiso calc 1 . .
    C C3 0.6745(2) -0.1969(3) 0.43776(14) 0.0322(6) Uani d 1 . .
    H H3A 0.6413 -0.2847 0.4476 0.039 Uiso calc 1 . .
    C C4 0.69455(19) -0.0733(3) 0.48342(13) 0.0268(5) Uani d 1 . .
    C C5 0.66956(19) -0.0753(3) 0.54877(13) 0.0270(5) Uani d 1 . .
    C C6 0.74263(18) 0.0061(3) 0.60332(13) 0.0274(5) Uani d 1 . .
    C C7 0.7695(2) -0.0525(3) 0.66834(14) 0.0338(6) Uani d 1 . .
    H H7A 0.7392 -0.1424 0.6789 0.041 Uiso calc 1 . .
    C C8 0.8421(2) 0.0244(4) 0.71756(14) 0.0368(6) Uani d 1 . .
    C C9 0.8860(2) 0.1599(3) 0.70255(14) 0.0387(6) Uani d 1 . .
    H H9A 0.9335 0.2116 0.7361 0.046 Uiso calc 1 . .
    C C10 0.8594(2) 0.2183(3) 0.63781(14) 0.0335(6) Uani d 1 . .
    H H10A 0.8887 0.3100 0.6281 0.040 Uiso calc 1 . .
    C C11 0.78929(18) 0.1415(3) 0.58699(12) 0.0267(5) Uani d 1 . .
    C C12 0.76325(18) 0.1893(3) 0.51620(12) 0.0257(5) Uani d 1 . .
    C C13 0.74330(18) 0.0599(3) 0.46719(13) 0.0261(5) Uani d 1 . .
    C C14 0.77265(19) 0.0651(3) 0.40707(13) 0.0289(5) Uani d 1 . .
    H H14A 0.8050 0.1527 0.3963 0.035 Uiso calc 1 . .
    C C15 0.58413(19) -0.1388(3) 0.55841(13) 0.0302(5) Uani d 1 . .
    C C16 0.5121(2) -0.2219(3) 0.50680(16) 0.0378(6) Uani d 1 . .
    C C17 0.5517(2) -0.1170(3) 0.61862(15) 0.0378(6) Uani d 1 . .
    C C18 0.75180(19) 0.3408(3) 0.49645(13) 0.0284(5) Uani d 1 . .
    C C19 0.7134(2) 0.3856(3) 0.42720(15) 0.0339(6) Uani d 1 . .
    C C20 0.7616(2) 0.4700(3) 0.54249(14) 0.0321(6) Uani d 1 . .
    C C21 0.0347(13) 0.5813(15) 0.6384(6) 0.056(2) Uani d 0.64(3) A 1
    H H21A 0.0581 0.5070 0.6717 0.067 Uiso calc 0.64(3) A 1
    C C22 0.0138(8) 0.7271(17) 0.6548(6) 0.056(2) Uani d 0.64(3) A 1
    H H22A 0.0236 0.7538 0.6999 0.067 Uiso calc 0.64(3) A 1
    C C23 -0.0229(8) 0.8398(13) 0.6045(8) 0.056(2) Uani d 0.64(3) A 1
    H H23A -0.0357 0.9403 0.6169 0.067 Uiso calc 0.64(3) A 1
    C C24 -0.0399(11) 0.8040(13) 0.5380(7) 0.0518(18) Uani d 0.64(3) A 1
    H H24A -0.0641 0.8800 0.5056 0.062 Uiso calc 0.64(3) A 1
    C C25 -0.021(2) 0.6496(16) 0.5176(5) 0.0454(16) Uani d 0.64(3) A 1
    C C26 -0.0409(12) 0.6062(14) 0.4505(5) 0.0456(19) Uani d 0.64(3) A 1
    H H26A -0.0691 0.6789 0.4175 0.055 Uiso calc 0.64(3) A 1
    C C27 -0.0204(18) 0.4574(16) 0.4311(8) 0.042(2) Uani d 0.64(3) A 1
    C C21B 0.044(2) 0.539(3) 0.6403(11) 0.057(3) Uani d 0.36(3) A 2
    H H21B 0.0732 0.4591 0.6693 0.068 Uiso calc 0.36(3) A 2
    C C22B 0.0259(15) 0.675(3) 0.6669(10) 0.060(3) Uani d 0.36(3) A 2
    H H22B 0.0391 0.6845 0.7134 0.072 Uiso calc 0.36(3) A 2
    C C23B -0.0122(14) 0.805(2) 0.6262(12) 0.054(3) Uani d 0.36(3) A 2
    H H23B -0.0224 0.8986 0.6462 0.065 Uiso calc 0.36(3) A 2
    C C24B -0.034(2) 0.795(2) 0.5578(11) 0.050(3) Uani d 0.36(3) A 2
    H H24B -0.0604 0.8803 0.5313 0.060 Uiso calc 0.36(3) A 2
    C C25B -0.017(4) 0.651(3) 0.5271(9) 0.046(2) Uani d 0.36(3) A 2
    C C26B -0.033(2) 0.632(3) 0.4583(10) 0.043(2) Uani d 0.36(3) A 2
    H H26B -0.0532 0.7175 0.4303 0.052 Uiso calc 0.36(3) A 2
    C C27B -0.020(3) 0.489(3) 0.4299(14) 0.042(3) Uani d 0.36(3) A 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    I1 C1 . 2.089(3) ?
    I2 C8 . 2.090(3) ?
    N1 C16 . 1.138(4) ?
    N2 C17 . 1.137(4) ?
    N3 C19 . 1.136(4) ?
    N4 C20 . 1.137(4) ?
    C1 C14 . 1.385(4) ?
    C1 C2 . 1.392(4) ?
    C2 C3 . 1.374(4) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.397(4) ?
    C3 H3A . 0.9300 ?
    C4 C13 . 1.409(3) ?
    C4 C5 . 1.472(4) ?
    C5 C15 . 1.358(3) ?
    C5 C6 . 1.474(4) ?
    C6 C7 . 1.386(4) ?
    C6 C11 . 1.410(3) ?
    C7 C8 . 1.390(4) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.383(4) ?
    C9 C10 . 1.380(4) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.390(4) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.465(3) ?
    C12 C18 . 1.359(3) ?
    C12 C13 . 1.477(3) ?
    C13 C14 . 1.399(4) ?
    C14 H14A . 0.9300 ?
    C15 C17 . 1.435(4) ?
    C15 C16 . 1.439(4) ?
    C18 C19 . 1.437(4) ?
    C18 C20 . 1.442(4) ?
    C21 C22 . 1.347(8) ?
    C21 C27 3_566 1.43(2) ?
    C21 H21A . 0.9300 ?
    C22 C23 . 1.411(8) ?
    C22 H22A . 0.9300 ?
    C23 C24 . 1.361(8) ?
    C23 H23A . 0.9300 ?
    C24 C25 . 1.435(6) ?
    C24 H24A . 0.9300 ?
    C25 C26 . 1.385(7) ?
    C25 C27 3_566 1.40(2) ?
    C26 C27 . 1.389(7) ?
    C26 H26A . 0.9300 ?
    C27 C25 3_566 1.40(2) ?
    C27 C21 3_566 1.43(2) ?
    C21B C22B . 1.343(10) ?
    C21B C27B 3_566 1.41(4) ?
    C21B H21B . 0.9300 ?
    C22B C23B . 1.410(10) ?
    C22B H22B . 0.9300 ?
    C23B C24B . 1.363(10) ?
    C23B H23B . 0.9300 ?
    C24B C25B . 1.436(8) ?
    C24B H24B . 0.9300 ?
    C25B C26B . 1.383(9) ?
    C25B C27B 3_566 1.50(4) ?
    C26B C27B . 1.390(9) ?
    C26B H26B . 0.9300 ?
    C27B C21B 3_566 1.42(4) ?
    C27B C25B 3_566 1.50(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
    C14 C1 C2 . . 120.6(2) ?
    C14 C1 I1 . . 120.99(19) ?
    C2 C1 I1 . . 118.40(19) ?
    C3 C2 C1 . . 119.8(2) ?
    C3 C2 H2A . . 120.1 ?
    C1 C2 H2A . . 120.1 ?
    C2 C3 C4 . . 121.2(2) ?
    C2 C3 H3A . . 119.4 ?
    C4 C3 H3A . . 119.4 ?
    C3 C4 C13 . . 118.7(2) ?
    C3 C4 C5 . . 123.6(2) ?
    C13 C4 C5 . . 117.7(2) ?
    C15 C5 C4 . . 123.8(2) ?
    C15 C5 C6 . . 121.7(2) ?
    C4 C5 C6 . . 114.5(2) ?
    C7 C6 C11 . . 120.4(2) ?
    C7 C6 C5 . . 121.4(2) ?
    C11 C6 C5 . . 118.2(2) ?
    C6 C7 C8 . . 119.4(2) ?
    C6 C7 H7A . . 120.3 ?
    C8 C7 H7A . . 120.3 ?
    C9 C8 C7 . . 120.7(3) ?
    C9 C8 I2 . . 120.4(2) ?
    C7 C8 I2 . . 118.9(2) ?
    C10 C9 C8 . . 120.0(3) ?
    C10 C9 H9A . . 120.0 ?
    C8 C9 H9A . . 120.0 ?
    C9 C10 C11 . . 120.7(3) ?
    C9 C10 H10A . . 119.6 ?
    C11 C10 H10A . . 119.6 ?
    C10 C11 C6 . . 118.8(2) ?
    C10 C11 C12 . . 123.8(2) ?
    C6 C11 C12 . . 117.3(2) ?
    C18 C12 C11 . . 123.0(2) ?
    C18 C12 C13 . . 121.9(2) ?
    C11 C12 C13 . . 114.9(2) ?
    C14 C13 C4 . . 120.1(2) ?
    C14 C13 C12 . . 122.3(2) ?
    C4 C13 C12 . . 117.6(2) ?
    C1 C14 C13 . . 119.6(2) ?
    C1 C14 H14A . . 120.2 ?
    C13 C14 H14A . . 120.2 ?
    C5 C15 C17 . . 123.4(3) ?
    C5 C15 C16 . . 123.3(2) ?
    C17 C15 C16 . . 113.1(2) ?
    N1 C16 C15 . . 178.0(3) ?
    N2 C17 C15 . . 175.1(3) ?
    C12 C18 C19 . . 122.5(2) ?
    C12 C18 C20 . . 123.8(2) ?
    C19 C18 C20 . . 113.1(2) ?
    N3 C19 C18 . . 176.2(3) ?
    N4 C20 C18 . . 175.6(3) ?
    C22 C21 C27 . 3_566 118.9(10) ?
    C22 C21 H21A . . 120.5 ?
    C27 C21 H21A 3_566 . 120.5 ?
    C21 C22 C23 . . 120.8(6) ?
    C21 C22 H22A . . 119.6 ?
    C23 C22 H22A . . 119.6 ?
    C24 C23 C22 . . 121.2(6) ?
    C24 C23 H23A . . 119.4 ?
    C22 C23 H23A . . 119.4 ?
    C23 C24 C25 . . 120.4(6) ?
    C23 C24 H24A . . 119.8 ?
    C25 C24 H24A . . 119.8 ?
    C26 C25 C27 . 3_566 120.6(10) ?
    C26 C25 C24 . . 122.4(7) ?
    C27 C25 C24 3_566 . 117.0(9) ?
    C25 C26 C27 . . 122.0(7) ?
    C25 C26 H26A . . 119.0 ?
    C27 C26 H26A . . 119.0 ?
    C26 C27 C25 . 3_566 117.3(11) ?
    C26 C27 C21 . 3_566 121.0(11) ?
    C25 C27 C21 3_566 3_566 121.5(11) ?
    C22B C21B C27B . 3_566 123.2(17) ?
    C22B C21B H21B . . 118.4 ?
    C27B C21B H21B 3_566 . 118.4 ?
    C21B C22B C23B . . 121.7(11) ?
    C21B C22B H22B . . 119.1 ?
    C23B C22B H22B . . 119.1 ?
    C24B C23B C22B . . 120.7(9) ?
    C24B C23B H23B . . 119.6 ?
    C22B C23B H23B . . 119.6 ?
    C23B C24B C25B . . 119.5(10) ?
    C23B C24B H24B . . 120.2 ?
    C25B C24B H24B . . 120.2 ?
    C26B C25B C24B . . 123.4(12) ?
    C26B C25B C27B . 3_566 116.7(17) ?
    C24B C25B C27B . 3_566 119.9(16) ?
    C25B C26B C27B . . 122.0(13) ?
    C25B C26B H26B . . 119.0 ?
    C27B C26B H26B . . 119.0 ?
    C26B C27B C21B . 3_566 124(2) ?
    C26B C27B C25B . 3_566 121(2) ?
    C21B C27B C25B 3_566 3_566 114.7(19) ?
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
    C14 C1 C2 C3 . . . . -1.7(4) ?
    I1 C1 C2 C3 . . . . 177.5(2) ?
    C1 C2 C3 C4 . . . . 0.4(4) ?
    C2 C3 C4 C13 . . . . 1.1(4) ?
    C2 C3 C4 C5 . . . . -177.5(2) ?
    C3 C4 C5 C15 . . . . -38.6(4) ?
    C13 C4 C5 C15 . . . . 142.9(2) ?
    C3 C4 C5 C6 . . . . 144.8(2) ?
    C13 C4 C5 C6 . . . . -33.8(3) ?
    C15 C5 C6 C7 . . . . 42.4(4) ?
    C4 C5 C6 C7 . . . . -140.9(2) ?
    C15 C5 C6 C11 . . . . -141.1(2) ?
    C4 C5 C6 C11 . . . . 35.6(3) ?
    C11 C6 C7 C8 . . . . 0.7(4) ?
    C5 C6 C7 C8 . . . . 177.1(2) ?
    C6 C7 C8 C9 . . . . 1.3(4) ?
    C6 C7 C8 I2 . . . . -176.85(19) ?
    C7 C8 C9 C10 . . . . -1.3(4) ?
    I2 C8 C9 C10 . . . . 176.8(2) ?
    C8 C9 C10 C11 . . . . -0.7(4) ?
    C9 C10 C11 C6 . . . . 2.6(4) ?
    C9 C10 C11 C12 . . . . -174.9(2) ?
    C7 C6 C11 C10 . . . . -2.6(4) ?
    C5 C6 C11 C10 . . . . -179.2(2) ?
    C7 C6 C11 C12 . . . . 175.1(2) ?
    C5 C6 C11 C12 . . . . -1.5(3) ?
    C10 C11 C12 C18 . . . . -40.7(4) ?
    C6 C11 C12 C18 . . . . 141.7(3) ?
    C10 C11 C12 C13 . . . . 143.3(2) ?
    C6 C11 C12 C13 . . . . -34.2(3) ?
    C3 C4 C13 C14 . . . . -1.4(4) ?
    C5 C4 C13 C14 . . . . 177.2(2) ?
    C3 C4 C13 C12 . . . . 179.7(2) ?
    C5 C4 C13 C12 . . . . -1.6(3) ?
    C18 C12 C13 C14 . . . . 41.2(4) ?
    C11 C12 C13 C14 . . . . -142.8(2) ?
    C18 C12 C13 C4 . . . . -140.0(3) ?
    C11 C12 C13 C4 . . . . 36.0(3) ?
    C2 C1 C14 C13 . . . . 1.4(4) ?
    I1 C1 C14 C13 . . . . -177.79(19) ?
    C4 C13 C14 C1 . . . . 0.2(4) ?
    C12 C13 C14 C1 . . . . 179.0(2) ?
    C4 C5 C15 C17 . . . . -168.8(2) ?
    C6 C5 C15 C17 . . . . 7.7(4) ?
    C4 C5 C15 C16 . . . . 4.9(4) ?
    C6 C5 C15 C16 . . . . -178.7(2) ?
    C11 C12 C18 C19 . . . . -171.6(2) ?
    C13 C12 C18 C19 . . . . 4.1(4) ?
    C11 C12 C18 C20 . . . . -1.5(4) ?
    C13 C12 C18 C20 . . . . 174.2(2) ?
    C27 C21 C22 C23 3_566 . . . 1(2) ?
    C21 C22 C23 C24 . . . . 1.2(14) ?
    C22 C23 C24 C25 . . . . 0.0(18) ?
    C23 C24 C25 C26 . . . . 177.2(19) ?
    C23 C24 C25 C27 . . . 3_566 -3(3) ?
    C27 C25 C26 C27 3_566 . . . -1(4) ?
    C24 C25 C26 C27 . . . . 178.8(18) ?
    C25 C26 C27 C25 . . . 3_566 1(4) ?
    C25 C26 C27 C21 . . . 3_566 -175(2) ?
    C27B C21B C22B C23B 3_566 . . . -4(4) ?
    C21B C22B C23B C24B . . . . 1(3) ?
    C22B C23B C24B C25B . . . . -1(3) ?
    C23B C24B C25B C26B . . . . -177(4) ?
    C23B C24B C25B C27B . . . 3_566 4(6) ?
    C24B C25B C26B C27B . . . . -177(3) ?
    C27B C25B C26B C27B 3_566 . . . 2(7) ?
    C25B C26B C27B C21B . . . 3_566 174(4) ?
    C25B C26B C27B C25B . . . 3_566 -2(7) ?
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
    C2 H2 N3 1_545 0.93 2.63 3.296(4) 129.2
    C9 H9 N2 2_656 0.93 2.59 3.432(4) 151.3
data_II
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1509827'
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane--pyrene (2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H6 I2 N4, 0.5(C16 H10)'
_chemical_formula_sum     'C28 H11 I2 N4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H6 I2 N4, 0.5C16 H10'
_chemical_formula_weight     657.21
_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     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7758(13)
_cell_length_b     12.0214(17)
_cell_length_c     13.3155(19)
_cell_angle_alpha     66.461(7)
_cell_angle_beta     74.489(7)
_cell_angle_gamma     74.462(7)
_cell_volume     1220.2(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9953
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     24.91
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'red'
_exptl_crystal_size_max     0.163
_exptl_crystal_size_mid     0.099
_exptl_crystal_size_min     0.095
_exptl_crystal_density_diffrn     1.789
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     626
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    0.00 1.00 0.00 0.0450
    0.00 -1.00 0.00 0.0340
    0.00 0.00 1.00 0.0360
    0.00 0.00 -1.00 0.0500
    -2.00 -1.00 -2.00 0.0560
    2.00 1.00 2.00 0.0560
    0.00 1.00 2.00 0.0370
_exptl_absorpt_coefficient_mu     2.601
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.677
_shelx_estimated_absorpt_T_max     0.790
_exptl_absorpt_correction_T_min     0.73424
_exptl_absorpt_correction_T_max     0.84536
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Sixteen
frame series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2013) then corrected for absorption by integration using
SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale
the combined data. No decay correction was applied.
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker Kappa APEXII CCD'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     30806
_diffrn_reflns_av_R_equivalents     0.0386
_diffrn_reflns_theta_min     2.640
_diffrn_reflns_theta_max     25.381
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions
suggested the ambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The highest peaks in the final difference Fourier map were in the
vicinity of the I atoms; the final map had no other significant
features. A final analysis of variance between observed and calculated
structure factors showed little dependence on amplitude and resolution.
;
_reflns_number_total     4480
_reflns_number_gt     3844
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0404
_refine_ls_R_factor_gt     0.0333
_refine_ls_wR_factor_gt     0.0804
_refine_ls_wR_factor_ref     0.0852
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     4480
_refine_ls_number_parameters     426
_refine_ls_number_restraints     500
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0337P)²+2.3821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.971
_refine_diff_density_min     -1.255
_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'
    'I' 'I' -0.4742 1.8119
                         '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
;
XPREP (Bruker, 2014) and SADABS (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_publication_material
;
XCIF (Bruker, 2014)
;
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
    I I1 0.74790(3) 0.05020(3) -0.02608(3) 0.05572(11) Uani d 1 . .
    I I2 0.25760(5) 0.70674(4) 0.39302(3) 0.08814(16) Uani d 1 . .
    N N3 1.0893(4) 0.0496(4) 0.2266(4) 0.0612(10) Uani d 1 . .
    N N4 1.0585(4) 0.3343(4) 0.3431(3) 0.0604(10) Uani d 1 . .
    C C1 0.6463(4) 0.1005(3) 0.1143(3) 0.0403(8) Uani d 1 . .
    C C2 0.4964(5) 0.0764(4) 0.1738(3) 0.0455(9) Uani d 1 . .
    H H2A 0.4430 0.0325 0.1547 0.055 Uiso calc 1 . .
    C C3 0.4261(4) 0.1174(4) 0.2614(3) 0.0427(9) Uani d 1 . .
    H H3A 0.3243 0.1022 0.3002 0.051 Uiso calc 1 . .
    C C4 0.5047(4) 0.1814(3) 0.2930(3) 0.0348(7) Uani d 1 . .
    C C5 0.4328(4) 0.2329(4) 0.3821(3) 0.0376(8) Uani d 1 . .
    C C6 0.4791(4) 0.3502(4) 0.3616(3) 0.0386(8) Uani d 1 . .
    C C7 0.3711(5) 0.4462(4) 0.3893(3) 0.0490(10) Uani d 1 . .
    H H7A 0.2665 0.4365 0.4256 0.059 Uiso calc 1 . .
    C C8 0.4206(5) 0.5564(4) 0.3626(4) 0.0536(11) Uani d 1 . .
    C C9 0.5766(6) 0.5720(4) 0.3116(4) 0.0543(10) Uani d 1 . .
    H H9A 0.6088 0.6457 0.2963 0.065 Uiso calc 1 . .
    C C10 0.6838(5) 0.4775(4) 0.2839(3) 0.0445(9) Uani d 1 . .
    H H10A 0.7889 0.4877 0.2496 0.053 Uiso calc 1 . .
    C C11 0.6374(4) 0.3668(3) 0.3062(3) 0.0354(8) Uani d 1 . .
    C C12 0.7432(4) 0.2682(3) 0.2693(3) 0.0331(7) Uani d 1 . .
    C C13 0.6602(4) 0.2015(3) 0.2344(3) 0.0333(7) Uani d 1 . .
    C C14 0.7291(4) 0.1620(3) 0.1449(3) 0.0368(8) Uani d 1 . .
    H H14A 0.8309 0.1767 0.1053 0.044 Uiso calc 1 . .
    N N1 0.261(2) -0.0356(14) 0.5130(14) 0.055(3) Uani d 0.61(4) A 1
    N N2 0.243(2) 0.2268(19) 0.6549(11) 0.070(3) Uani d 0.61(4) A 1
    C C15 0.339(4) 0.171(2) 0.4769(15) 0.043(3) Uani d 0.61(4) A 1
    C C16 0.296(2) 0.0552(17) 0.4970(16) 0.045(3) Uani d 0.61(4) A 1
    C C17 0.288(2) 0.2053(16) 0.5739(10) 0.049(3) Uani d 0.61(4) A 1
    N N1B 0.215(3) -0.010(2) 0.524(2) 0.060(5) Uani d 0.39(4) A 2
    N N2B 0.204(3) 0.273(3) 0.6355(19) 0.067(4) Uani d 0.39(4) A 2
    C C15B 0.329(6) 0.185(4) 0.477(2) 0.044(3) Uani d 0.39(4) A 2
    C C16B 0.271(4) 0.074(3) 0.501(3) 0.049(4) Uani d 0.39(4) A 2
    C C17B 0.258(3) 0.238(3) 0.5619(17) 0.049(3) Uani d 0.39(4) A 2
    C C18 0.9032(4) 0.2366(3) 0.2703(3) 0.0355(8) Uani d 1 . .
    C C19 1.0039(4) 0.1322(4) 0.2438(3) 0.0428(9) Uani d 1 . .
    C C20 0.9868(4) 0.2937(4) 0.3109(3) 0.0423(9) Uani d 1 . .
    C C21 0.791(3) 0.682(3) 1.026(3) 0.077(3) Uani d 0.640(6) B 1
    H H21 0.7001 0.7423 1.0279 0.093 Uiso calc 0.640(6) B 1
    C C22 0.7924(10) 0.5881(8) 0.9795(7) 0.065(2) Uani d 0.640(6) B 1
    C C23 0.6650(11) 0.5838(9) 0.9391(7) 0.080(2) Uani d 0.640(6) B 1
    H H23 0.5705 0.6416 0.9405 0.096 Uiso calc 0.640(6) B 1
    C C24 0.6792(11) 0.4963(9) 0.8984(8) 0.075(2) Uani d 0.640(6) B 1
    H H24 0.5905 0.4947 0.8737 0.090 Uiso calc 0.640(6) B 1
    C C25 0.8082(12) 0.4116(9) 0.8901(8) 0.072(2) Uani d 0.640(6) B 1
    H H25 0.8113 0.3564 0.8564 0.087 Uiso calc 0.640(6) B 1
    C C26 0.9347(10) 0.4972(9) 0.9790(10) 0.0555(19) Uani d 0.640(6) B 1
    C C27 0.9463(11) 0.4059(7) 0.9347(6) 0.0643(16) Uani d 0.640(6) B 1
    C C28 1.0891(13) 0.3172(8) 0.9353(8) 0.074(2) Uani d 0.640(6) B 1
    H H28 1.0973 0.2560 0.9071 0.089 Uiso calc 0.640(6) B 1
    C C21B 0.725(2) 0.6277(15) 0.9780(15) 0.076(3) Uani d 0.360(6) B 2
    H H21B 0.6208 0.6597 0.9649 0.092 Uiso calc 0.360(6) B 2
    C C22B 0.8136(15) 0.5211(12) 0.9446(11) 0.066(2) Uani d 0.360(6) B 2
    C C23B 0.760(2) 0.4655(16) 0.8895(16) 0.075(3) Uani d 0.360(6) B 2
    H H23B 0.6586 0.4941 0.8707 0.091 Uiso calc 0.360(6) B 2
    C C24B 0.8581(19) 0.3703(13) 0.8642(13) 0.074(3) Uani d 0.360(6) B 2
    H H24B 0.8203 0.3371 0.8253 0.089 Uiso calc 0.360(6) B 2
    C C25B 0.9996(18) 0.3197(13) 0.8881(12) 0.076(3) Uani d 0.360(6) B 2
    H H25B 1.0584 0.2525 0.8681 0.091 Uiso calc 0.360(6) B 2
    C C26B 0.9703(18) 0.4736(15) 0.9718(19) 0.057(3) Uani d 0.360(6) B 2
    C C27B 1.0654(18) 0.3699(12) 0.9470(12) 0.065(3) Uani d 0.360(6) B 2
    C C28B 1.219(4) 0.323(5) 0.978(6) 0.073(5) Uani d 0.360(6) B 2
    H H28B 1.2801 0.2521 0.9650 0.088 Uiso calc 0.360(6) B 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    I1 C1 . 2.093(4) ?
    I2 C8 . 2.089(4) ?
    N3 C19 . 1.138(5) ?
    N4 C20 . 1.137(5) ?
    C1 C2 . 1.380(5) ?
    C1 C14 . 1.387(5) ?
    C2 C3 . 1.377(6) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.393(5) ?
    C3 H3A . 0.9300 ?
    C4 C13 . 1.409(5) ?
    C4 C5 . 1.472(5) ?
    C5 C15B . 1.362(8) ?
    C5 C15 . 1.362(7) ?
    C5 C6 . 1.472(5) ?
    C6 C7 . 1.391(5) ?
    C6 C11 . 1.413(5) ?
    C7 C8 . 1.386(6) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.382(6) ?
    C9 C10 . 1.374(6) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.390(5) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.464(5) ?
    C12 C18 . 1.355(5) ?
    C12 C13 . 1.477(5) ?
    C13 C14 . 1.387(5) ?
    C14 H14A . 0.9300 ?
    N1 C16 . 1.135(8) ?
    N2 C17 . 1.151(8) ?
    C15 C17 . 1.437(9) ?
    C15 C16 . 1.439(8) ?
    N1B C16B . 1.137(9) ?
    N2B C17B . 1.151(9) ?
    C15B C17B . 1.436(10) ?
    C15B C16B . 1.439(9) ?
    C18 C19 . 1.440(6) ?
    C18 C20 . 1.442(5) ?
    C21 C28 2_767 1.290(18) ?
    C21 C22 . 1.48(2) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.384(13) ?
    C22 C26 . 1.423(11) ?
    C23 C24 . 1.329(14) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.317(13) ?
    C24 H24 . 0.9300 ?
    C25 C27 . 1.461(12) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.409(10) ?
    C26 C26 2_767 1.431(15) ?
    C27 C28 . 1.411(14) ?
    C28 C21 2_767 1.290(18) ?
    C28 H28 . 0.9300 ?
    C21B C28B 2_767 1.23(4) ?
    C21B C22B . 1.48(2) ?
    C21B H21B . 0.9300 ?
    C22B C23B . 1.395(15) ?
    C22B C26B . 1.425(12) ?
    C23B C24B . 1.336(15) ?
    C23B H23B . 0.9300 ?
    C24B C25B . 1.290(14) ?
    C24B H24B . 0.9300 ?
    C25B C27B . 1.456(14) ?
    C25B H25B . 0.9300 ?
    C26B C27B . 1.408(12) ?
    C26B C26B 2_767 1.42(2) ?
    C27B C28B . 1.420(16) ?
    C28B C21B 2_767 1.23(4) ?
    C28B H28B . 0.9300 ?
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 C14 . . 120.4(3) ?
    C2 C1 I1 . . 120.4(3) ?
    C14 C1 I1 . . 119.2(3) ?
    C3 C2 C1 . . 119.8(3) ?
    C3 C2 H2A . . 120.1 ?
    C1 C2 H2A . . 120.1 ?
    C2 C3 C4 . . 121.3(3) ?
    C2 C3 H3A . . 119.4 ?
    C4 C3 H3A . . 119.4 ?
    C3 C4 C13 . . 118.4(3) ?
    C3 C4 C5 . . 123.8(3) ?
    C13 C4 C5 . . 117.7(3) ?
    C15B C5 C6 . . 118.7(11) ?
    C15 C5 C6 . . 124.7(7) ?
    C15B C5 C4 . . 126.8(11) ?
    C15 C5 C4 . . 120.8(7) ?
    C6 C5 C4 . . 114.5(3) ?
    C7 C6 C11 . . 119.5(4) ?
    C7 C6 C5 . . 122.5(3) ?
    C11 C6 C5 . . 118.0(3) ?
    C8 C7 C6 . . 119.5(4) ?
    C8 C7 H7A . . 120.3 ?
    C6 C7 H7A . . 120.3 ?
    C9 C8 C7 . . 121.4(4) ?
    C9 C8 I2 . . 118.0(3) ?
    C7 C8 I2 . . 120.6(3) ?
    C10 C9 C8 . . 119.4(4) ?
    C10 C9 H9A . . 120.3 ?
    C8 C9 H9A . . 120.3 ?
    C9 C10 C11 . . 121.0(4) ?
    C9 C10 H10A . . 119.5 ?
    C11 C10 H10A . . 119.5 ?
    C10 C11 C6 . . 119.3(3) ?
    C10 C11 C12 . . 122.7(3) ?
    C6 C11 C12 . . 117.9(3) ?
    C18 C12 C11 . . 123.4(3) ?
    C18 C12 C13 . . 122.2(3) ?
    C11 C12 C13 . . 114.4(3) ?
    C14 C13 C4 . . 120.0(3) ?
    C14 C13 C12 . . 121.9(3) ?
    C4 C13 C12 . . 118.0(3) ?
    C1 C14 C13 . . 120.0(3) ?
    C1 C14 H14A . . 120.0 ?
    C13 C14 H14A . . 120.0 ?
    C5 C15 C17 . . 123.2(10) ?
    C5 C15 C16 . . 124.4(11) ?
    C17 C15 C16 . . 112.1(7) ?
    N1 C16 C15 . . 179.6(15) ?
    N2 C17 C15 . . 175.7(12) ?
    C5 C15B C17B . . 125.7(16) ?
    C5 C15B C16B . . 122.1(17) ?
    C17B C15B C16B . . 112.1(10) ?
    N1B C16B C15B . . 175(2) ?
    N2B C17B C15B . . 175(2) ?
    C12 C18 C19 . . 123.2(3) ?
    C12 C18 C20 . . 123.9(3) ?
    C19 C18 C20 . . 112.5(3) ?
    N3 C19 C18 . . 176.0(4) ?
    N4 C20 C18 . . 176.8(4) ?
    C28 C21 C22 2_767 . 123.2(12) ?
    C28 C21 H21 2_767 . 118.4 ?
    C22 C21 H21 . . 118.4 ?
    C23 C22 C26 . . 119.4(10) ?
    C23 C22 C21 . . 124.3(9) ?
    C26 C22 C21 . . 116.2(8) ?
    C24 C23 C22 . . 119.4(9) ?
    C24 C23 H23 . . 120.3 ?
    C22 C23 H23 . . 120.3 ?
    C25 C24 C23 . . 125.5(9) ?
    C25 C24 H24 . . 117.2 ?
    C23 C24 H24 . . 117.2 ?
    C24 C25 C27 . . 118.9(9) ?
    C24 C25 H25 . . 120.5 ?
    C27 C25 H25 . . 120.5 ?
    C27 C26 C22 . . 119.8(7) ?
    C27 C26 C26 . 2_767 121.4(9) ?
    C22 C26 C26 . 2_767 118.8(10) ?
    C26 C27 C28 . . 118.4(8) ?
    C26 C27 C25 . . 116.8(8) ?
    C28 C27 C25 . . 124.8(7) ?
    C21 C28 C27 2_767 . 122.0(12) ?
    C21 C28 H28 2_767 . 119.0 ?
    C27 C28 H28 . . 119.0 ?
    C28B C21B C22B 2_767 . 124.6(18) ?
    C28B C21B H21B 2_767 . 117.7 ?
    C22B C21B H21B . . 117.7 ?
    C23B C22B C26B . . 118.4(12) ?
    C23B C22B C21B . . 127.1(11) ?
    C26B C22B C21B . . 114.5(12) ?
    C24B C23B C22B . . 118.9(12) ?
    C24B C23B H23B . . 120.5 ?
    C22B C23B H23B . . 120.5 ?
    C25B C24B C23B . . 126.7(13) ?
    C25B C24B H24B . . 116.7 ?
    C23B C24B H24B . . 116.7 ?
    C24B C25B C27B . . 118.7(11) ?
    C24B C25B H25B . . 120.6 ?
    C27B C25B H25B . . 120.6 ?
    C27B C26B C26B . 2_767 119.2(13) ?
    C27B C26B C22B . . 120.1(10) ?
    C26B C26B C22B 2_767 . 120.6(13) ?
    C26B C27B C28B . . 118.6(13) ?
    C26B C27B C25B . . 117.1(11) ?
    C28B C27B C25B . . 124.3(13) ?
    C21B C28B C27B 2_767 . 122(2) ?
    C21B C28B H28B 2_767 . 118.8 ?
    C27B C28B H28B . . 118.8 ?
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
    C14 C1 C2 C3 . . . . 2.4(6) ?
    I1 C1 C2 C3 . . . . -175.6(3) ?
    C1 C2 C3 C4 . . . . -1.2(6) ?
    C2 C3 C4 C13 . . . . -1.1(5) ?
    C2 C3 C4 C5 . . . . 176.8(4) ?
    C3 C4 C5 C15B . . . . 34(3) ?
    C13 C4 C5 C15B . . . . -148(3) ?
    C3 C4 C5 C15 . . . . 38(2) ?
    C13 C4 C5 C15 . . . . -144(2) ?
    C3 C4 C5 C6 . . . . -144.9(3) ?
    C13 C4 C5 C6 . . . . 33.1(4) ?
    C15B C5 C6 C7 . . . . -38(3) ?
    C15 C5 C6 C7 . . . . -43(2) ?
    C4 C5 C6 C7 . . . . 140.8(3) ?
    C15B C5 C6 C11 . . . . 145(3) ?
    C15 C5 C6 C11 . . . . 141(2) ?
    C4 C5 C6 C11 . . . . -35.7(4) ?
    C11 C6 C7 C8 . . . . -0.2(5) ?
    C5 C6 C7 C8 . . . . -176.7(3) ?
    C6 C7 C8 C9 . . . . -1.8(6) ?
    C6 C7 C8 I2 . . . . 175.8(3) ?
    C7 C8 C9 C10 . . . . 2.0(6) ?
    I2 C8 C9 C10 . . . . -175.7(3) ?
    C8 C9 C10 C11 . . . . 0.0(6) ?
    C9 C10 C11 C6 . . . . -2.1(5) ?
    C9 C10 C11 C12 . . . . 174.4(4) ?
    C7 C6 C11 C10 . . . . 2.2(5) ?
    C5 C6 C11 C10 . . . . 178.8(3) ?
    C7 C6 C11 C12 . . . . -174.5(3) ?
    C5 C6 C11 C12 . . . . 2.2(5) ?
    C10 C11 C12 C18 . . . . 39.3(5) ?
    C6 C11 C12 C18 . . . . -144.2(3) ?
    C10 C11 C12 C13 . . . . -143.1(3) ?
    C6 C11 C12 C13 . . . . 33.5(4) ?
    C3 C4 C13 C14 . . . . 2.4(5) ?
    C5 C4 C13 C14 . . . . -175.7(3) ?
    C3 C4 C13 C12 . . . . -179.4(3) ?
    C5 C4 C13 C12 . . . . 2.6(5) ?
    C18 C12 C13 C14 . . . . -40.1(5) ?
    C11 C12 C13 C14 . . . . 142.2(3) ?
    C18 C12 C13 C4 . . . . 141.7(3) ?
    C11 C12 C13 C4 . . . . -36.1(4) ?
    C2 C1 C14 C13 . . . . -1.1(6) ?
    I1 C1 C14 C13 . . . . 176.8(3) ?
    C4 C13 C14 C1 . . . . -1.2(5) ?
    C12 C13 C14 C1 . . . . -179.5(3) ?
    C6 C5 C15 C17 . . . . -7(4) ?
    C4 C5 C15 C17 . . . . 169.1(18) ?
    C6 C5 C15 C16 . . . . -179.2(15) ?
    C4 C5 C15 C16 . . . . -3(3) ?
    C6 C5 C15B C17B . . . . 0(6) ?
    C4 C5 C15B C17B . . . . -179(3) ?
    C6 C5 C15B C16B . . . . 177(3) ?
    C4 C5 C15B C16B . . . . -2(6) ?
    C11 C12 C18 C19 . . . . 174.0(3) ?
    C13 C12 C18 C19 . . . . -3.6(5) ?
    C11 C12 C18 C20 . . . . 1.9(6) ?
    C13 C12 C18 C20 . . . . -175.6(3) ?
    C28 C21 C22 C23 2_767 . . . 179(2) ?
    C28 C21 C22 C26 2_767 . . . 0(4) ?
    C26 C22 C23 C24 . . . . -1.4(13) ?
    C21 C22 C23 C24 . . . . 180(2) ?
    C22 C23 C24 C25 . . . . -1.6(14) ?
    C23 C24 C25 C27 . . . . 4.0(14) ?
    C23 C22 C26 C27 . . . . 1.7(15) ?
    C21 C22 C26 C27 . . . . -179(2) ?
    C23 C22 C26 C26 . . . 2_767 -180.0(12) ?
    C21 C22 C26 C26 . . . 2_767 -1(3) ?
    C22 C26 C27 C28 . . . . 179.9(9) ?
    C26 C26 C27 C28 2_767 . . . 1.7(19) ?
    C22 C26 C27 C25 . . . . 0.6(14) ?
    C26 C26 C27 C25 2_767 . . . -177.7(13) ?
    C24 C25 C27 C26 . . . . -3.3(13) ?
    C24 C25 C27 C28 . . . . 177.4(8) ?
    C26 C27 C28 C21 . . . 2_767 -1(3) ?
    C25 C27 C28 C21 . . . 2_767 178(2) ?
    C28B C21B C22B C23B 2_767 . . . -176(5) ?
    C28B C21B C22B C26B 2_767 . . . 3(5) ?
    C26B C22B C23B C24B . . . . 0(3) ?
    C21B C22B C23B C24B . . . . 178.9(15) ?
    C22B C23B C24B C25B . . . . 2(3) ?
    C23B C24B C25B C27B . . . . -1(3) ?
    C23B C22B C26B C27B . . . . -2(3) ?
    C21B C22B C26B C27B . . . . 178.4(18) ?
    C23B C22B C26B C26B . . . 2_767 -180(3) ?
    C21B C22B C26B C26B . . . 2_767 1(3) ?
    C26B C26B C27B C28B 2_767 . . . -1(5) ?
    C22B C26B C27B C28B . . . . -178(4) ?
    C26B C26B C27B C25B 2_767 . . . -179(2) ?
    C22B C26B C27B C25B . . . . 3(3) ?
    C24B C25B C27B C26B . . . . -2(2) ?
    C24B C25B C27B C28B . . . . 180(4) ?
    C26B C27B C28B C21B . . . 2_767 -3(9) ?
    C25B C27B C28B C21B . . . 2_767 176(5) ?
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
    C2 H2 I1 2_655 0.93 3.24 4.144(4) 163.7
    C9 H9 N2 2_666 0.93 2.60 3.443(17) 150.1
    C9 H9 N2B 2_666 0.93 2.62 3.38(3) 138.8
_shelxl_version_number     2014/6
data_III
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1509828'
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane--tetrathiafulvalene
(2/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H6 I2 N4, 0.5(C6 H4 S4)'
_chemical_formula_sum     'C23 H8 I2 N4 S2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C20 H6 I2 N4, 0.5C6 H4 S4'
_chemical_formula_weight     658.25
_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     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.615(2)
_cell_length_b     11.631(3)
_cell_length_c     12.450(3)
_cell_angle_alpha     80.247(9)
_cell_angle_beta     74.695(9)
_cell_angle_gamma     70.392(8)
_cell_volume     1129.0(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9509
_cell_measurement_theta_min     2.64
_cell_measurement_theta_max     27.16
_cell_measurement_temperature     273(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'black'
_exptl_crystal_size_max     0.455
_exptl_crystal_size_mid     0.272
_exptl_crystal_size_min     0.116
_exptl_crystal_density_diffrn     1.936
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1.00 0.00 0.00 0.0360
    -1.00 0.00 0.00 0.0580
    0.00 0.00 1.00 0.1750
    0.00 0.00 -1.00 0.1110
    0.00 1.00 1.00 0.1000
    0.00 -1.00 -1.00 0.1020
    -2.00 -1.00 2.00 0.1350
    0.00 -2.00 1.00 0.2030
_exptl_absorpt_coefficient_mu     2.989
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.343
_shelx_estimated_absorpt_T_max     0.723
_exptl_absorpt_correction_T_min     0.92580
_exptl_absorpt_correction_T_max     0.97809
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Seven frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2013) then corrected for absorption by integration using
SAINT/SADABS v2014/2 (Bruker, 2014) to sort, merge, and scale
the combined data. No decay correction was applied.
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'microfocus sealed tube'
_diffrn_radiation_monochromator     'multilayer mirrors'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29346
_diffrn_reflns_av_R_equivalents     0.0273
_diffrn_reflns_theta_min     2.412
_diffrn_reflns_theta_max     27.201
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct methods (Sheldrick, 2014). Systematic conditions
suggested the ambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The highest peaks in the final difference Fourier map were in the
vicinity of the I atoms; the final map had no other significant
features. A final analysis of variance between observed and calculated
structure factors showed little dependence on amplitude and resolution.
;
_reflns_number_total     4993
_reflns_number_gt     4572
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0442
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.1012
_refine_ls_wR_factor_ref     0.1036
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     4993
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0457P)²+2.8841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.714
_refine_diff_density_min     -1.199
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.0373(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'I' 'I' -0.4742 1.8119
                         '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
;
XPREP (Bruker, 2014) and SADABS (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_publication_material
;
XCIF (Bruker, 2014)
;
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
    I I1 0.79542(4) 1.18759(3) 0.96735(3) 0.05333(13) Uani d 1 . .
    I I2 1.25872(5) 0.29582(3) 0.57238(3) 0.07177(15) Uani d 1 . .
    N N1 1.2833(7) 1.0080(5) 0.4452(4) 0.0795(14) Uani d 1 . .
    N N2 1.2746(7) 0.6866(5) 0.3438(4) 0.0766(14) Uani d 1 . .
    N N3 0.4216(5) 1.0444(4) 0.8397(5) 0.0657(12) Uani d 1 . .
    N N4 0.4563(5) 0.7109(4) 0.7340(4) 0.0601(10) Uani d 1 . .
    C C1 0.9011(5) 1.0500(3) 0.8589(3) 0.0388(8) Uani d 1 . .
    C C2 1.0566(5) 1.0435(4) 0.7869(4) 0.0421(8) Uani d 1 . .
    H H2 1.1132 1.0980 0.7900 0.051 Uiso calc 1 . .
    C C3 1.1270(5) 0.9564(4) 0.7110(3) 0.0401(8) Uani d 1 . .
    H H3 1.2332 0.9505 0.6650 0.048 Uiso calc 1 . .
    C C4 1.0414(4) 0.8766(3) 0.7020(3) 0.0350(7) Uani d 1 . .
    C C5 1.1037(4) 0.7892(3) 0.6161(3) 0.0360(7) Uani d 1 . .
    C C6 1.0562(5) 0.6759(3) 0.6477(3) 0.0370(7) Uani d 1 . .
    C C7 1.1595(5) 0.5644(4) 0.6067(3) 0.0437(9) Uani d 1 . .
    H H7 1.2625 0.5598 0.5568 0.052 Uiso calc 1 . .
    C C8 1.1085(6) 0.4604(4) 0.6402(4) 0.0461(9) Uani d 1 . .
    C C9 0.9592(6) 0.4636(4) 0.7182(4) 0.0454(9) Uani d 1 . .
    H H9 0.9278 0.3927 0.7420 0.054 Uiso calc 1 . .
    C C10 0.8578(5) 0.5732(4) 0.7600(3) 0.0400(8) Uani d 1 . .
    H H10 0.7579 0.5757 0.8128 0.048 Uiso calc 1 . .
    C C11 0.9022(4) 0.6802(3) 0.7246(3) 0.0350(7) Uani d 1 . .
    C C12 0.7950(4) 0.7993(3) 0.7659(3) 0.0329(7) Uani d 1 . .
    C C13 0.8846(4) 0.8827(3) 0.7772(3) 0.0331(7) Uani d 1 . .
    C C14 0.8180(5) 0.9676(3) 0.8569(3) 0.0368(7) Uani d 1 . .
    H H14 0.7176 0.9689 0.9087 0.044 Uiso calc 1 . .
    C C15 1.1941(5) 0.8135(4) 0.5111(3) 0.0423(8) Uani d 1 . .
    C C16 1.2413(6) 0.9236(4) 0.4769(4) 0.0516(10) Uani d 1 . .
    C C17 1.2375(6) 0.7395(5) 0.4204(4) 0.0549(11) Uani d 1 . .
    C C18 0.6243(4) 0.8335(3) 0.7830(3) 0.0362(7) Uani d 1 . .
    C C19 0.5145(5) 0.9524(4) 0.8147(4) 0.0447(9) Uani d 1 . .
    C C20 0.5350(5) 0.7613(4) 0.7567(4) 0.0432(9) Uani d 1 . .
    S S1 0.20489(15) 0.56951(10) 0.90038(10) 0.0505(3) Uani d 1 . .
    S S2 0.17172(15) 0.32114(10) 0.94620(10) 0.0509(3) Uani d 1 . .
    C C21 0.0782(5) 0.4771(4) 0.9691(3) 0.0416(8) Uani d 1 . .
    C C22 0.3719(6) 0.4506(4) 0.8411(5) 0.0583(12) Uani d 1 . .
    H H22 0.4695 0.4648 0.7957 0.070 Uiso calc 1 . .
    C C23 0.3572(5) 0.3372(4) 0.8623(4) 0.0558(11) Uani d 1 . .
    H H23 0.4441 0.2701 0.8327 0.067 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    I1 C1 . 2.079(4) ?
    I2 C8 . 2.088(4) ?
    N1 C16 . 1.132(7) ?
    N2 C17 . 1.139(6) ?
    N3 C19 . 1.135(6) ?
    N4 C20 . 1.143(6) ?
    C1 C14 . 1.381(5) ?
    C1 C2 . 1.387(6) ?
    C2 C3 . 1.378(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.398(5) ?
    C3 H3 . 0.9300 ?
    C4 C13 . 1.413(5) ?
    C4 C5 . 1.471(5) ?
    C5 C15 . 1.371(5) ?
    C5 C6 . 1.470(5) ?
    C6 C7 . 1.395(5) ?
    C6 C11 . 1.408(5) ?
    C7 C8 . 1.385(6) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.386(6) ?
    C9 C10 . 1.377(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.390(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.473(5) ?
    C12 C18 . 1.355(5) ?
    C12 C13 . 1.470(5) ?
    C13 C14 . 1.393(5) ?
    C14 H14 . 0.9300 ?
    C15 C17 . 1.430(6) ?
    C15 C16 . 1.435(6) ?
    C18 C20 . 1.437(5) ?
    C18 C19 . 1.440(5) ?
    S1 C22 . 1.725(5) ?
    S1 C21 . 1.750(4) ?
    S2 C23 . 1.712(5) ?
    S2 C21 . 1.759(4) ?
    C21 C21 2_567 1.342(8) ?
    C22 C23 . 1.343(7) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
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
    C14 C1 C2 . . 120.5(4) ?
    C14 C1 I1 . . 121.1(3) ?
    C2 C1 I1 . . 118.5(3) ?
    C3 C2 C1 . . 119.9(4) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 121.1(3) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C3 C4 C13 . . 118.4(3) ?
    C3 C4 C5 . . 123.3(3) ?
    C13 C4 C5 . . 118.3(3) ?
    C15 C5 C6 . . 121.6(4) ?
    C15 C5 C4 . . 122.5(4) ?
    C6 C5 C4 . . 115.8(3) ?
    C7 C6 C11 . . 119.0(4) ?
    C7 C6 C5 . . 122.6(3) ?
    C11 C6 C5 . . 118.4(3) ?
    C8 C7 C6 . . 120.0(4) ?
    C8 C7 H7 . . 120.0 ?
    C6 C7 H7 . . 120.0 ?
    C7 C8 C9 . . 121.1(4) ?
    C7 C8 I2 . . 119.6(3) ?
    C9 C8 I2 . . 119.3(3) ?
    C10 C9 C8 . . 119.1(4) ?
    C10 C9 H9 . . 120.5 ?
    C8 C9 H9 . . 120.5 ?
    C9 C10 C11 . . 121.2(4) ?
    C9 C10 H10 . . 119.4 ?
    C11 C10 H10 . . 119.4 ?
    C10 C11 C6 . . 119.6(3) ?
    C10 C11 C12 . . 122.6(3) ?
    C6 C11 C12 . . 117.9(3) ?
    C18 C12 C13 . . 122.2(3) ?
    C18 C12 C11 . . 121.5(3) ?
    C13 C12 C11 . . 116.0(3) ?
    C14 C13 C4 . . 120.0(3) ?
    C14 C13 C12 . . 122.2(3) ?
    C4 C13 C12 . . 117.8(3) ?
    C1 C14 C13 . . 120.0(3) ?
    C1 C14 H14 . . 120.0 ?
    C13 C14 H14 . . 120.0 ?
    C5 C15 C17 . . 124.5(4) ?
    C5 C15 C16 . . 123.2(4) ?
    C17 C15 C16 . . 112.1(4) ?
    N1 C16 C15 . . 176.7(5) ?
    N2 C17 C15 . . 175.6(6) ?
    C12 C18 C20 . . 123.4(3) ?
    C12 C18 C19 . . 123.8(3) ?
    C20 C18 C19 . . 112.3(3) ?
    N3 C19 C18 . . 176.8(4) ?
    N4 C20 C18 . . 175.5(4) ?
    C22 S1 C21 . . 94.9(2) ?
    C23 S2 C21 . . 95.6(2) ?
    C21 C21 S1 2_567 . 122.4(4) ?
    C21 C21 S2 2_567 . 123.5(4) ?
    S1 C21 S2 . . 114.0(2) ?
    C23 C22 S1 . . 118.3(4) ?
    C23 C22 H22 . . 120.9 ?
    S1 C22 H22 . . 120.9 ?
    C22 C23 S2 . . 117.2(3) ?
    C22 C23 H23 . . 121.4 ?
    S2 C23 H23 . . 121.4 ?
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
    C14 C1 C2 C3 . . . . 1.6(6) ?
    I1 C1 C2 C3 . . . . -177.5(3) ?
    C1 C2 C3 C4 . . . . 2.5(6) ?
    C2 C3 C4 C13 . . . . -3.6(6) ?
    C2 C3 C4 C5 . . . . 174.5(4) ?
    C3 C4 C5 C15 . . . . -32.7(6) ?
    C13 C4 C5 C15 . . . . 145.4(4) ?
    C3 C4 C5 C6 . . . . 150.1(4) ?
    C13 C4 C5 C6 . . . . -31.8(5) ?
    C15 C5 C6 C7 . . . . 34.5(6) ?
    C4 C5 C6 C7 . . . . -148.3(4) ?
    C15 C5 C6 C11 . . . . -147.0(4) ?
    C4 C5 C6 C11 . . . . 30.2(5) ?
    C11 C6 C7 C8 . . . . 1.1(6) ?
    C5 C6 C7 C8 . . . . 179.5(4) ?
    C6 C7 C8 C9 . . . . -2.9(6) ?
    C6 C7 C8 I2 . . . . 177.1(3) ?
    C7 C8 C9 C10 . . . . 2.1(6) ?
    I2 C8 C9 C10 . . . . -177.9(3) ?
    C8 C9 C10 C11 . . . . 0.5(6) ?
    C9 C10 C11 C6 . . . . -2.3(6) ?
    C9 C10 C11 C12 . . . . 178.7(4) ?
    C7 C6 C11 C10 . . . . 1.5(5) ?
    C5 C6 C11 C10 . . . . -177.0(3) ?
    C7 C6 C11 C12 . . . . -179.5(3) ?
    C5 C6 C11 C12 . . . . 2.0(5) ?
    C10 C11 C12 C18 . . . . -39.3(5) ?
    C6 C11 C12 C18 . . . . 141.7(4) ?
    C10 C11 C12 C13 . . . . 146.1(4) ?
    C6 C11 C12 C13 . . . . -32.9(5) ?
    C3 C4 C13 C14 . . . . 0.8(5) ?
    C5 C4 C13 C14 . . . . -177.4(3) ?
    C3 C4 C13 C12 . . . . 179.3(3) ?
    C5 C4 C13 C12 . . . . 1.1(5) ?
    C18 C12 C13 C14 . . . . 35.1(5) ?
    C11 C12 C13 C14 . . . . -150.3(3) ?
    C18 C12 C13 C4 . . . . -143.3(4) ?
    C11 C12 C13 C4 . . . . 31.2(5) ?
    C2 C1 C14 C13 . . . . -4.4(6) ?
    I1 C1 C14 C13 . . . . 174.7(3) ?
    C4 C13 C14 C1 . . . . 3.2(5) ?
    C12 C13 C14 C1 . . . . -175.3(3) ?
    C6 C5 C15 C17 . . . . 5.9(6) ?
    C4 C5 C15 C17 . . . . -171.1(4) ?
    C6 C5 C15 C16 . . . . 179.4(4) ?
    C4 C5 C15 C16 . . . . 2.4(6) ?
    C13 C12 C18 C20 . . . . 170.4(3) ?
    C11 C12 C18 C20 . . . . -3.9(6) ?
    C13 C12 C18 C19 . . . . -0.6(6) ?
    C11 C12 C18 C19 . . . . -174.9(4) ?
    C22 S1 C21 C21 . . . 2_567 -178.8(5) ?
    C22 S1 C21 S2 . . . . -0.5(3) ?
    C23 S2 C21 C21 . . . 2_567 179.0(5) ?
    C23 S2 C21 S1 . . . . 0.7(3) ?
    C21 S1 C22 C23 . . . . 0.0(5) ?
    S1 C22 C23 S2 . . . . 0.5(6) ?
    C21 S2 C23 C22 . . . . -0.7(5) ?
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
    C23 H23 N3 1_545 0.93 2.68 3.310(6) 125.5
_shelxl_version_number     2014/6
