##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section B. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section B, 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_DIEABipy
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2016-08-25
_journal_date_accepted     2016-10-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2017
_journal_volume     73
_journal_issue      2
_journal_page_first     163
_journal_page_last     167
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2052520616016450
_journal_coeditor_code     AO5017
_database_code_depnum_ccdc_archive     'CCDC 1483700'
_chemical_name_systematic
;
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H8 I2, 2(C10 H8 N2)'
_chemical_formula_sum     'C38 H24 I2 N4'
_chemical_formula_weight     790.45
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,-z
_cell_length_a     9.7245(4)
_cell_length_b     10.1191(4)
_cell_length_c     17.5288(7)
_cell_angle_alpha     87.839(3)
_cell_angle_beta     80.433(4)
_cell_angle_gamma     70.331(4)
_cell_volume     1601.35(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.485
_exptl_crystal_size_mid     0.290
_exptl_crystal_size_min     0.226
_exptl_crystal_density_diffrn     1.639
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     772
_exptl_absorpt_coefficient_mu     1.997
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     SADABS
_exptl_absorpt_correction_T_min     0.497
_exptl_absorpt_correction_T_max     0.629
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo)X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometet with Saphire3 detector
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16639
_diffrn_reflns_av_R_equivalents     0.0230
_diffrn_reflns_av_sigmaI/netI     0.0407
_diffrn_reflns_theta_min     4.17
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     22
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_reflns_number_total     9306
_reflns_number_gt     6617
_reflns_threshold_expression     'i > 2σ(i)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0629
_refine_ls_R_factor_gt     0.0382
_refine_ls_wR_factor_gt     0.0698
_refine_ls_wR_factor_ref     0.0782
_refine_ls_goodness_of_fit_ref     0.998
_refine_ls_restrained_S_all     0.998
_refine_ls_number_reflns     9306
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
                      'W=1/[Σ²(FO²)+(0.0294P)²] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.576
_refine_diff_density_min     -0.609
_refine_ls_extinction_method     none
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'
    I I -0.4742 1.8119 ' 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'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, 2013)
;
_computing_structure_refinement
;
SHELXS-2013 (Sheldrick, 2013)
;
_computing_molecular_graphics
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material
;
SHELXL-2013 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.34436(2) 0.26571(2) 0.49644(2) 0.05450(10) Uani d . 1.000 . .
    I I2 0.15213(2) 0.65666(2) 0.37374(2) 0.05360(10) Uani d . 1.000 . .
    C C1 0.3940(3) -0.0154(3) 0.28349(18) 0.0465(10) Uani d . 1.000 . .
    C C2 0.3559(3) 0.0572(3) 0.21365(16) 0.0412(8) Uani d . 1.000 . .
    C C3 0.3039(3) 0.2032(3) 0.21089(15) 0.0396(8) Uani d . 1.000 . .
    C C4 0.2652(3) 0.2725(3) 0.14387(15) 0.0399(8) Uani d . 1.000 . .
    C C5 0.2093(3) 0.4249(3) 0.14120(16) 0.0456(9) Uani d . 1.000 . .
    C C6 0.1734(4) 0.4879(3) 0.07338(19) 0.0609(11) Uani d . 1.000 . .
    C C7 0.1894(4) 0.4082(4) 0.00608(19) 0.0662(11) Uani d . 1.000 . .
    C C8 0.2397(3) 0.2664(4) 0.00682(18) 0.0586(11) Uani d . 1.000 . .
    C C9 0.2797(3) 0.1929(3) 0.07526(16) 0.0445(9) Uani d . 1.000 . .
    C C10 0.3312(3) 0.0469(3) 0.07840(17) 0.0504(10) Uani d . 1.000 . .
    C C11 0.3701(3) -0.0231(3) 0.14535(17) 0.0449(9) Uani d . 1.000 . .
    C C12 0.4180(3) -0.1720(3) 0.1491(2) 0.0592(11) Uani d . 1.000 . .
    C C13 0.4506(4) -0.2369(3) 0.2155(2) 0.0650(13) Uani d . 1.000 . .
    C C14 0.4403(3) -0.1595(3) 0.2835(2) 0.0596(11) Uani d . 1.000 . .
    C C15 0.3833(3) 0.0641(3) 0.35117(18) 0.0488(10) Uani d . 1.000 . .
    C C16 0.3726(3) 0.1369(3) 0.40589(18) 0.0534(11) Uani d . 1.000 . .
    C C17 0.1928(3) 0.5032(3) 0.21048(18) 0.0480(9) Uani d . 1.000 . .
    C C18 0.1805(3) 0.5603(3) 0.27019(19) 0.0532(10) Uani d . 1.000 . .
    N N1 0.6980(3) 0.5555(3) 0.37764(16) 0.0642(10) Uani d . 1.000 . .
    N N2 0.7543(4) 0.2073(4) 0.02593(18) 0.0822(14) Uani d . 1.000 . .
    C C19 0.7968(4) 0.5588(4) 0.3162(2) 0.0687(12) Uani d . 1.000 . .
    C C20 0.8159(3) 0.4875(3) 0.2477(2) 0.0611(11) Uani d . 1.000 . .
    C C21 0.7257(3) 0.4092(3) 0.24036(17) 0.0450(9) Uani d . 1.000 . .
    C C22 0.6225(3) 0.4058(3) 0.30497(18) 0.0536(10) Uani d . 1.000 . .
    C C23 0.6138(4) 0.4785(3) 0.37111(19) 0.0625(12) Uani d . 1.000 . .
    C C24 0.7366(3) 0.3373(3) 0.16730(17) 0.0470(9) Uani d . 1.000 . .
    C C25 0.8711(3) 0.2668(3) 0.12202(18) 0.0555(11) Uani d . 1.000 . .
    C C26 0.8739(4) 0.2036(4) 0.0534(2) 0.0677(12) Uani d . 1.000 . .
    C C27 0.6254(4) 0.2776(5) 0.0691(2) 0.0927(18) Uani d . 1.000 . .
    C C28 0.6104(4) 0.3423(4) 0.1387(2) 0.0728(14) Uani d . 1.000 . .
    N N3 0.8800(3) 1.2073(3) 0.48766(17) 0.0644(10) Uani d . 1.000 . .
    N N4 0.9040(3) 0.8622(3) 0.13937(18) 0.0767(11) Uani d . 1.000 . .
    C C29 0.9659(4) 1.2191(4) 0.4232(2) 0.0647(11) Uani d . 1.000 . .
    C C30 0.9767(3) 1.1530(3) 0.35416(19) 0.0561(11) Uani d . 1.000 . .
    C C31 0.8908(3) 1.0687(3) 0.35069(16) 0.0428(8) Uani d . 1.000 . .
    C C32 0.7986(4) 1.0580(3) 0.41798(18) 0.0622(11) Uani d . 1.000 . .
    C C33 0.7985(4) 1.1267(4) 0.48464(19) 0.0701(14) Uani d . 1.000 . .
    C C34 0.8947(3) 0.9976(3) 0.27823(16) 0.0444(9) Uani d . 1.000 . .
    C C35 1.0237(3) 0.9456(3) 0.22497(17) 0.0508(10) Uani d . 1.000 . .
    C C36 1.0223(4) 0.8806(3) 0.15847(19) 0.0630(11) Uani d . 1.000 . .
    C C37 0.7820(4) 0.9129(5) 0.1899(2) 0.0965(18) Uani d . 1.000 . .
    C C38 0.7698(4) 0.9807(4) 0.2590(2) 0.0764(14) Uani d . 1.000 . .
    H H3 0.29490 0.25540 0.25510 0.0470 Uiso c RU 1.000 . .
    H H6 0.13770 0.58540 0.07160 0.0730 Uiso c RU 1.000 . .
    H H7 0.16490 0.45380 -0.03930 0.0790 Uiso c RU 1.000 . .
    H H8 0.24850 0.21590 -0.03800 0.0700 Uiso c RU 1.000 . .
    H H10 0.33980 -0.00520 0.03420 0.0600 Uiso c RU 1.000 . .
    H H12 0.42690 -0.22510 0.10520 0.0710 Uiso c RU 1.000 . .
    H H13 0.48060 -0.33430 0.21700 0.0780 Uiso c RU 1.000 . .
    H H14 0.46500 -0.20680 0.32850 0.0720 Uiso c RU 1.000 . .
    H H20 0.51700 0.38890 0.16630 0.0880 Uiso c RU 1.000 . .
    H H21 0.53940 0.28310 0.05070 0.1120 Uiso c RU 1.000 . .
    H H22 0.96560 0.15530 0.02460 0.0810 Uiso c RU 1.000 . .
    H H23 0.95910 0.26220 0.13790 0.0670 Uiso c RU 1.000 . .
    H H25 0.55970 0.35440 0.30340 0.0640 Uiso c RU 1.000 . .
    H H26 0.54500 0.47340 0.41380 0.0750 Uiso c RU 1.000 . .
    H H27 0.85680 0.61240 0.31950 0.0820 Uiso c RU 1.000 . .
    H H28 0.88850 0.49180 0.20680 0.0730 Uiso c RU 1.000 . .
    H H30 0.67930 1.01410 0.29170 0.0920 Uiso c RU 1.000 . .
    H H31 0.69640 0.90230 0.17820 0.1160 Uiso c RU 1.000 . .
    H H32 1.11080 0.84680 0.12420 0.0760 Uiso c RU 1.000 . .
    H H33 1.11120 0.95500 0.23460 0.0610 Uiso c RU 1.000 . .
    H H35 0.73700 1.00480 0.41840 0.0750 Uiso c RU 1.000 . .
    H H36 0.73800 1.11570 0.52970 0.0840 Uiso c RU 1.000 . .
    H H37 1.02330 1.27610 0.42440 0.0780 Uiso c RU 1.000 . .
    H H38 1.04030 1.16460 0.31060 0.0670 Uiso c RU 1.000 . .
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C16 . . 2.016(3) yes
    I1 N1 . 2_666 2.795(3) yes
    I2 C18 . . 2.027(3) yes
    I2 N3 . 2_676 2.758(3) yes
    N1 C23 . . 1.326(5) yes
    N1 C19 . . 1.326(5) yes
    N2 C26 . . 1.320(6) yes
    N2 C27 . . 1.332(6) yes
    N3 C29 . . 1.316(5) yes
    N3 C33 . . 1.322(5) yes
    N4 C36 . . 1.322(5) yes
    N4 C37 . . 1.316(5) yes
    C1 C15 . . 1.428(4) no
    C1 C14 . . 1.374(4) no
    C1 C2 . . 1.441(4) no
    C2 C3 . . 1.393(4) no
    C2 C11 . . 1.434(4) no
    C3 C4 . . 1.386(4) no
    C4 C5 . . 1.454(4) no
    C4 C9 . . 1.434(4) no
    C5 C17 . . 1.432(4) no
    C5 C6 . . 1.368(4) no
    C6 C7 . . 1.412(5) no
    C7 C8 . . 1.352(5) no
    C8 C9 . . 1.427(4) no
    C9 C10 . . 1.393(4) no
    C10 C11 . . 1.388(4) no
    C11 C12 . . 1.422(4) no
    C12 C13 . . 1.346(5) no
    C13 C14 . . 1.422(5) no
    C15 C16 . . 1.201(4) no
    C17 C18 . . 1.184(4) no
    C3 H3 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8 . . 0.9300 no
    C10 H10 . . 0.9300 no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14 . . 0.9300 no
    C19 C20 . . 1.378(5) no
    C20 C21 . . 1.388(4) no
    C21 C22 . . 1.391(4) no
    C21 C24 . . 1.468(4) no
    C22 C23 . . 1.372(4) no
    C24 C28 . . 1.386(5) no
    C24 C25 . . 1.385(4) no
    C25 C26 . . 1.376(5) no
    C27 C28 . . 1.369(5) no
    C19 H27 . . 0.9300 no
    C20 H28 . . 0.9300 no
    C22 H25 . . 0.9300 no
    C23 H26 . . 0.9300 no
    C25 H23 . . 0.9300 no
    C26 H22 . . 0.9300 no
    C27 H21 . . 0.9300 no
    C28 H20 . . 0.9300 no
    C29 C30 . . 1.376(5) no
    C30 C31 . . 1.389(4) no
    C31 C32 . . 1.382(4) no
    C31 C34 . . 1.472(4) no
    C32 C33 . . 1.382(5) no
    C34 C35 . . 1.388(4) no
    C34 C38 . . 1.378(5) no
    C35 C36 . . 1.364(4) no
    C37 C38 . . 1.383(5) no
    C29 H37 . . 0.9300 no
    C30 H38 . . 0.9300 no
    C32 H35 . . 0.9300 no
    C33 H36 . . 0.9300 no
    C35 H33 . . 0.9300 no
    C36 H32 . . 0.9300 no
    C37 H31 . . 0.9300 no
    C38 H30 . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C16 I1 N1 . . 2_666 179.38(10) yes
    C18 I2 N3 . . 2_676 178.00(10) yes
    C19 N1 C23 . . . 116.7(3) yes
    C26 N2 C27 . . . 115.9(3) yes
    C29 N3 C33 . . . 116.8(3) yes
    C36 N4 C37 . . . 114.9(3) yes
    C2 C1 C15 . . . 119.2(3) no
    C2 C1 C14 . . . 119.3(3) no
    C14 C1 C15 . . . 121.4(3) no
    C1 C2 C11 . . . 119.1(3) no
    C3 C2 C11 . . . 119.1(3) no
    C1 C2 C3 . . . 121.9(3) no
    C2 C3 C4 . . . 121.6(3) no
    C3 C4 C5 . . . 121.6(2) no
    C3 C4 C9 . . . 119.6(3) no
    C5 C4 C9 . . . 118.8(2) no
    C4 C5 C17 . . . 118.2(2) no
    C6 C5 C17 . . . 122.6(3) no
    C4 C5 C6 . . . 119.2(3) no
    C5 C6 C7 . . . 121.4(3) no
    C6 C7 C8 . . . 120.8(3) no
    C7 C8 C9 . . . 121.1(3) no
    C8 C9 C10 . . . 122.8(3) no
    C4 C9 C8 . . . 118.7(3) no
    C4 C9 C10 . . . 118.6(3) no
    C9 C10 C11 . . . 122.1(3) no
    C2 C11 C12 . . . 119.0(3) no
    C10 C11 C12 . . . 122.0(3) no
    C2 C11 C10 . . . 119.0(3) no
    C11 C12 C13 . . . 120.7(3) no
    C12 C13 C14 . . . 121.3(3) no
    C1 C14 C13 . . . 120.6(3) no
    C1 C15 C16 . . . 176.7(3) no
    I1 C16 C15 . . . 177.0(3) yes
    C5 C17 C18 . . . 175.9(3) no
    I2 C18 C17 . . . 177.8(3) yes
    C2 C3 H3 . . . 119.00 no
    C4 C3 H3 . . . 119.00 no
    C7 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 no
    C6 C7 H7 . . . 120.00 no
    C8 C7 H7 . . . 120.00 no
    C9 C8 H8 . . . 119.00 no
    C7 C8 H8 . . . 119.00 no
    C9 C10 H10 . . . 119.00 no
    C11 C10 H10 . . . 119.00 no
    C11 C12 H12 . . . 120.00 no
    C13 C12 H12 . . . 120.00 no
    C14 C13 H13 . . . 119.00 no
    C12 C13 H13 . . . 119.00 no
    C1 C14 H14 . . . 120.00 no
    C13 C14 H14 . . . 120.00 no
    N1 C19 C20 . . . 123.9(4) yes
    C19 C20 C21 . . . 119.4(3) no
    C20 C21 C24 . . . 121.4(3) no
    C22 C21 C24 . . . 122.1(3) no
    C20 C21 C22 . . . 116.5(3) no
    C21 C22 C23 . . . 119.7(3) no
    N1 C23 C22 . . . 123.8(3) yes
    C21 C24 C25 . . . 122.5(3) no
    C25 C24 C28 . . . 116.7(3) no
    C21 C24 C28 . . . 120.8(3) no
    C24 C25 C26 . . . 119.7(3) no
    N2 C26 C25 . . . 124.0(4) yes
    N2 C27 C28 . . . 124.7(4) yes
    C24 C28 C27 . . . 119.0(4) no
    N1 C19 H27 . . . 118.00 no
    C20 C19 H27 . . . 118.00 no
    C19 C20 H28 . . . 120.00 no
    C21 C20 H28 . . . 120.00 no
    C23 C22 H25 . . . 120.00 no
    C21 C22 H25 . . . 120.00 no
    N1 C23 H26 . . . 118.00 no
    C22 C23 H26 . . . 118.00 no
    C24 C25 H23 . . . 120.00 no
    C26 C25 H23 . . . 120.00 no
    C25 C26 H22 . . . 118.00 no
    N2 C26 H22 . . . 118.00 no
    N2 C27 H21 . . . 118.00 no
    C28 C27 H21 . . . 118.00 no
    C27 C28 H20 . . . 120.00 no
    C24 C28 H20 . . . 121.00 no
    N3 C29 C30 . . . 124.5(4) yes
    C29 C30 C31 . . . 118.8(3) no
    C30 C31 C32 . . . 116.8(3) no
    C30 C31 C34 . . . 121.5(3) no
    C32 C31 C34 . . . 121.7(3) no
    C31 C32 C33 . . . 119.7(3) no
    N3 C33 C32 . . . 123.4(3) yes
    C31 C34 C35 . . . 122.0(3) no
    C31 C34 C38 . . . 121.8(3) no
    C35 C34 C38 . . . 116.2(3) no
    C34 C35 C36 . . . 120.0(3) no
    N4 C36 C35 . . . 124.6(3) yes
    N4 C37 C38 . . . 125.7(4) yes
    C34 C38 C37 . . . 118.5(3) no
    N3 C29 H37 . . . 118.00 no
    C30 C29 H37 . . . 118.00 no
    C29 C30 H38 . . . 121.00 no
    C31 C30 H38 . . . 121.00 no
    C31 C32 H35 . . . 120.00 no
    C33 C32 H35 . . . 120.00 no
    N3 C33 H36 . . . 118.00 no
    C32 C33 H36 . . . 118.00 no
    C34 C35 H33 . . . 120.00 no
    C36 C35 H33 . . . 120.00 no
    N4 C36 H32 . . . 118.00 no
    C35 C36 H32 . . . 118.00 no
    N4 C37 H31 . . . 117.00 no
    C38 C37 H31 . . . 117.00 no
    C34 C38 H30 . . . 121.00 no
    C37 C38 H30 . . . 121.00 no
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
    C19 N1 C23 C22 . . . . -1.1(5) no
    C23 N1 C19 C20 . . . . -0.2(5) no
    C26 N2 C27 C28 . . . . -1.0(6) no
    C27 N2 C26 C25 . . . . 0.0(6) no
    C29 N3 C33 C32 . . . . -0.9(5) no
    C33 N3 C29 C30 . . . . -0.5(6) no
    C36 N4 C37 C38 . . . . -0.4(6) no
    C37 N4 C36 C35 . . . . 0.4(5) no
    C15 C1 C2 C3 . . . . -2.3(5) no
    C14 C1 C2 C11 . . . . -1.2(5) no
    C14 C1 C2 C3 . . . . 178.0(3) no
    C2 C1 C14 C13 . . . . -0.1(5) no
    C15 C1 C2 C11 . . . . 178.6(3) no
    C15 C1 C14 C13 . . . . -179.9(3) no
    C1 C2 C11 C12 . . . . 1.5(4) no
    C1 C2 C3 C4 . . . . -179.0(3) no
    C11 C2 C3 C4 . . . . 0.2(5) no
    C1 C2 C11 C10 . . . . 179.0(3) no
    C3 C2 C11 C10 . . . . -0.2(5) no
    C3 C2 C11 C12 . . . . -177.7(3) no
    C2 C3 C4 C5 . . . . 179.3(3) no
    C2 C3 C4 C9 . . . . -0.5(5) no
    C3 C4 C5 C17 . . . . -0.9(5) no
    C9 C4 C5 C6 . . . . -0.5(5) no
    C9 C4 C5 C17 . . . . 178.9(3) no
    C3 C4 C9 C8 . . . . -179.8(3) no
    C3 C4 C9 C10 . . . . 0.7(5) no
    C5 C4 C9 C8 . . . . 0.5(4) no
    C3 C4 C5 C6 . . . . 179.7(3) no
    C5 C4 C9 C10 . . . . -179.1(3) no
    C4 C5 C6 C7 . . . . 0.0(5) no
    C17 C5 C6 C7 . . . . -179.4(3) no
    C5 C6 C7 C8 . . . . 0.6(6) no
    C6 C7 C8 C9 . . . . -0.7(6) no
    C7 C8 C9 C10 . . . . 179.6(3) no
    C7 C8 C9 C4 . . . . 0.2(5) no
    C4 C9 C10 C11 . . . . -0.7(5) no
    C8 C9 C10 C11 . . . . 179.8(3) no
    C9 C10 C11 C12 . . . . 177.9(3) no
    C9 C10 C11 C2 . . . . 0.5(5) no
    C10 C11 C12 C13 . . . . -177.9(3) no
    C2 C11 C12 C13 . . . . -0.5(5) no
    C11 C12 C13 C14 . . . . -0.9(5) no
    C12 C13 C14 C1 . . . . 1.2(5) no
    N1 C19 C20 C21 . . . . 1.5(5) no
    C19 C20 C21 C22 . . . . -1.5(4) no
    C19 C20 C21 C24 . . . . 176.8(3) no
    C20 C21 C24 C25 . . . . 41.2(4) no
    C22 C21 C24 C28 . . . . 42.3(4) no
    C20 C21 C24 C28 . . . . -136.0(3) no
    C22 C21 C24 C25 . . . . -140.5(3) no
    C20 C21 C22 C23 . . . . 0.4(4) no
    C24 C21 C22 C23 . . . . -177.9(3) no
    C21 C22 C23 N1 . . . . 0.9(5) no
    C21 C24 C25 C26 . . . . -178.8(3) no
    C28 C24 C25 C26 . . . . -1.5(5) no
    C25 C24 C28 C27 . . . . 0.6(5) no
    C21 C24 C28 C27 . . . . 177.9(3) no
    C24 C25 C26 N2 . . . . 1.3(5) no
    N2 C27 C28 C24 . . . . 0.8(6) no
    N3 C29 C30 C31 . . . . 0.8(5) no
    C29 C30 C31 C32 . . . . 0.4(4) no
    C29 C30 C31 C34 . . . . 178.6(3) no
    C30 C31 C32 C33 . . . . -1.7(5) no
    C34 C31 C32 C33 . . . . -179.9(3) no
    C30 C31 C34 C35 . . . . 35.2(4) no
    C30 C31 C34 C38 . . . . -143.9(3) no
    C32 C31 C34 C35 . . . . -146.7(3) no
    C32 C31 C34 C38 . . . . 34.3(5) no
    C31 C32 C33 N3 . . . . 2.0(6) no
    C31 C34 C35 C36 . . . . -179.9(3) no
    C38 C34 C35 C36 . . . . -0.8(4) no
    C31 C34 C38 C37 . . . . 180.0(3) no
    C35 C34 C38 C37 . . . . 0.8(5) no
    C34 C35 C36 N4 . . . . 0.1(5) no
    N4 C37 C38 C34 . . . . -0.3(6) no
data_DIEAAzopy
_audit_creation_method     'PLATON <TABLE ACC> option'
_database_code_depnum_ccdc_archive     'CCDC 1483701'
_chemical_name_systematic
;
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H8 I2, 2(C10 H8 N4)'
_chemical_formula_sum     'C38 H24 I2 N8'
_chemical_formula_weight     846.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,y,1/2-z
    3 -x,-y,-z
    4 x,-y,1/2+z
    5 1/2+x,1/2+y,z
    6 1/2-x,1/2+y,1/2-z
    7 1/2-x,1/2-y,-z
    8 1/2+x,1/2-y,1/2+z
_cell_length_a     16.0411(11)
_cell_length_b     22.6435(11)
_cell_length_c     9.6728(7)
_cell_angle_alpha     90
_cell_angle_beta     102.322(7)
_cell_angle_gamma     90
_cell_volume     3432.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.360
_exptl_crystal_size_mid     0.343
_exptl_crystal_size_min     0.168
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.638
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     1656
_exptl_absorpt_coefficient_mu     1.873
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     SADABS
_exptl_absorpt_correction_T_min     0.527
_exptl_absorpt_correction_T_max     0.684
_exptl_special_details
;
;
_diffrn_ambient_temperature     296
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
;
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10609
_diffrn_reflns_av_R_equivalents     0.0217
_diffrn_reflns_av_sigmaI/netI     0.0331
_diffrn_reflns_theta_min     4.13
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     13
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_reflns_number_total     5009
_reflns_number_gt     3363
_reflns_threshold_expression     'i > 2σ(i)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0671
_refine_ls_R_factor_gt     0.0382
_refine_ls_wR_factor_gt     0.0808
_refine_ls_wR_factor_ref     0.0921
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     5009
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     'calc'
_refine_ls_weighting_details
              'W=1/[Σ²(FO²)+(0.0365P)²+0.6702P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.671
_refine_diff_density_min     -0.549
_refine_ls_extinction_method     'none'
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'
    I I -0.4742 1.8119 ' 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'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_structure_solution
;
SHELXS-2013 (Sheldrick, 2013)
;
_computing_structure_refinement
;
SHELXS-2013 (Sheldrick, 2013)
;
_computing_molecular_graphics
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material
;
SHELXL-2013 (Sheldrick, 2013) and PLATON (Spek, 2003)
;
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    I I1 0.11678(2) 0.03974(2) 0.47853(2) 0.06160(10) Uani d . 1.000 . .
    C C1 0.10921(17) 0.24424(14) 0.4744(3) 0.0529(10) Uani d . 1.000 . .
    C C2 0.05328(16) 0.27465(11) 0.3602(3) 0.0464(8) Uani d . 1.000 . .
    C C3 0.00000 0.24495(16) 0.25000 0.0453(11) Uani d STP 1.000 . .
    C C4 0.00000 0.36717(17) 0.25000 0.0601(15) Uani d STP 1.000 . .
    C C5 0.05281(18) 0.33782(12) 0.3612(3) 0.0529(10) Uani d . 1.000 . .
    C C6 0.1077(2) 0.36789(16) 0.4742(4) 0.0702(13) Uani d . 1.000 . .
    C C7 0.1597(2) 0.33846(16) 0.5787(4) 0.0776(14) Uani d . 1.000 . .
    C C8 0.1611(2) 0.27596(15) 0.5800(4) 0.0670(12) Uani d . 1.000 . .
    C C9 0.11126(17) 0.18099(14) 0.4761(3) 0.0534(10) Uani d . 1.000 . .
    C C10 0.11289(18) 0.12900(15) 0.4772(3) 0.0582(11) Uani d . 1.000 . .
    N N1 0.12352(16) 0.91594(13) 0.4845(3) 0.0645(10) Uani d . 1.000 . .
    N N2 0.12331(18) 0.73037(15) 0.4638(3) 0.0754(11) Uani d . 1.000 . .
    N N3 0.16147(18) 0.70573(14) 0.5668(3) 0.0707(11) Uani d . 1.000 . .
    N N4 0.1429(3) 0.52001(17) 0.5485(6) 0.1127(18) Uani d . 1.000 . .
    C C11 0.12799(18) 0.79467(14) 0.4809(4) 0.0579(11) Uani d . 1.000 . .
    C C12 0.15148(19) 0.82470(14) 0.6076(3) 0.0606(11) Uani d . 1.000 . .
    C C13 0.1481(2) 0.88537(14) 0.6035(4) 0.0661(11) Uani d . 1.000 . .
    C C14 0.1016(2) 0.88556(17) 0.3654(4) 0.0758(14) Uani d . 1.000 . .
    C C15 0.1021(2) 0.82556(16) 0.3588(4) 0.0733(12) Uani d . 1.000 . .
    C C16 0.1532(2) 0.64095(15) 0.5488(5) 0.0736(13) Uani d . 1.000 . .
    C C17 0.1930(2) 0.60900(16) 0.6627(5) 0.0808(14) Uani d . 1.000 . .
    C C18 0.1856(3) 0.54862(18) 0.6574(7) 0.103(2) Uani d . 1.000 . .
    C C19 0.1052(4) 0.5503(2) 0.4359(8) 0.126(3) Uani d . 1.000 . .
    C C20 0.1079(3) 0.6132(2) 0.4322(6) 0.0964(19) Uani d . 1.000 . .
    H H3 0.00000 0.20390 0.25000 0.0540 Uiso c RUP 1.000 . .
    H H4 0.00000 0.40820 0.25000 0.0720 Uiso c RUP 1.000 . .
    H H6 0.10760 0.40900 0.47580 0.0840 Uiso c RU 1.000 . .
    H H7 0.19510 0.35930 0.65100 0.0930 Uiso c RU 1.000 . .
    H H8 0.19750 0.25620 0.65300 0.0800 Uiso c RU 1.000 . .
    H H12 0.16900 0.80460 0.69260 0.0730 Uiso c RU 1.000 . .
    H H13 0.16380 0.90600 0.68820 0.0790 Uiso c RU 1.000 . .
    H H14 0.08500 0.90650 0.28120 0.0910 Uiso c RU 1.000 . .
    H H15 0.08500 0.80610 0.27270 0.0880 Uiso c RU 1.000 . .
    H H17 0.22460 0.62760 0.74260 0.0970 Uiso c RU 1.000 . .
    H H18 0.21250 0.52700 0.73600 0.1240 Uiso c RU 1.000 . .
    H H19 0.07600 0.53010 0.35670 0.1510 Uiso c RU 1.000 . .
    H H20 0.08000 0.63430 0.35340 0.1160 Uiso c RU 1.000 . .
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    I1 C10 . . 2.022(3) yes
    I1 N1 . 1_545 2.805(3) yes
    N1 C13 . . 1.329(5) yes
    N1 C14 . . 1.323(5) yes
    N2 N3 . . 1.191(4) yes
    N2 C11 . . 1.466(5) yes
    N3 C16 . . 1.480(5) yes
    N4 C19 . . 1.320(9) yes
    N4 C18 . . 1.300(8) yes
    C1 C2 . . 1.441(4) no
    C1 C8 . . 1.375(5) no
    C1 C9 . . 1.433(4) no
    C2 C3 . . 1.389(3) no
    C2 C5 . . 1.431(4) no
    C4 C5 . 2_555 1.388(3) no
    C4 C5 . . 1.388(3) no
    C5 C6 . . 1.422(5) no
    C6 C7 . . 1.342(5) no
    C7 C8 . . 1.415(5) no
    C9 C10 . . 1.178(5) no
    C3 H3 . . 0.9300 no
    C4 H4 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C7 H7 . . 0.9300 no
    C8 H8 . . 0.9300 no
    C11 C12 . . 1.382(5) no
    C11 C15 . . 1.359(5) no
    C12 C13 . . 1.375(4) no
    C14 C15 . . 1.360(5) no
    C16 C17 . . 1.358(6) no
    C16 C20 . . 1.358(7) no
    C17 C18 . . 1.372(5) no
    C19 C20 . . 1.426(6) no
    C12 H12 . . 0.9300 no
    C13 H13 . . 0.9300 no
    C14 H14 . . 0.9300 no
    C15 H15 . . 0.9300 no
    C17 H17 . . 0.9300 no
    C18 H18 . . 0.9300 no
    C19 H19 . . 0.9300 no
    C20 H20 . . 0.9300 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 I1 N1 . . 1.545 179.17(10) yes
    C13 N1 C14 . . . 117.3(3) yes
    N3 N2 C11 . . . 111.5(3) yes
    N2 N3 C16 . . . 110.4(3) yes
    C18 N4 C19 . . . 118.6(4) yes
    C2 C1 C9 . . . 119.7(3) no
    C8 C1 C9 . . . 120.3(3) no
    C2 C1 C8 . . . 120.0(3) no
    C1 C2 C3 . . . 122.5(3) no
    C1 C2 C5 . . . 118.4(3) no
    C3 C2 C5 . . . 119.1(3) no
    C2 C3 C2 . . 2_555 122.1(3) no
    C5 C4 C5 . . 2_555 122.8(3) no
    C2 C5 C6 . . . 118.7(3) no
    C4 C5 C6 . . . 122.8(3) no
    C2 C5 C4 . . . 118.5(3) no
    C5 C6 C7 . . . 121.6(3) no
    C6 C7 C8 . . . 120.6(3) no
    C1 C8 C7 . . . 120.7(3) no
    C1 C9 C10 . . . 179.9(4) no
    I1 C10 C9 . . . 179.5(3) yes
    C2 C3 H3 2_555 . . 119.00 no
    C2 C3 H3 . . . 119.00 no
    C5 C4 H4 . . . 119.00 no
    C5 C4 H4 2_555 . . 119.00 no
    C5 C6 H6 . . . 119.00 no
    C7 C6 H6 . . . 119.00 no
    C8 C7 H7 . . . 120.00 no
    C6 C7 H7 . . . 120.00 no
    C1 C8 H8 . . . 120.00 no
    C7 C8 H8 . . . 120.00 no
    N2 C11 C12 . . . 125.9(3) yes
    N2 C11 C15 . . . 114.5(3) yes
    C12 C11 C15 . . . 119.5(3) no
    C11 C12 C13 . . . 117.7(3) no
    N1 C13 C12 . . . 123.2(3) yes
    N1 C14 C15 . . . 123.9(4) yes
    C11 C15 C14 . . . 118.5(3) no
    N3 C16 C17 . . . 114.7(4) yes
    N3 C16 C20 . . . 125.1(4) yes
    C17 C16 C20 . . . 120.2(4) no
    C16 C17 C18 . . . 118.6(4) no
    N4 C18 C17 . . . 123.6(5) yes
    N4 C19 C20 . . . 121.9(6) yes
    C16 C20 C19 . . . 117.1(5) no
    C11 C12 H12 . . . 121.00 no
    C13 C12 H12 . . . 121.00 no
    N1 C13 H13 . . . 118.00 no
    C12 C13 H13 . . . 118.00 no
    N1 C14 H14 . . . 118.00 no
    C15 C14 H14 . . . 118.00 no
    C11 C15 H15 . . . 121.00 no
    C14 C15 H15 . . . 121.00 no
    C16 C17 H17 . . . 121.00 no
    C18 C17 H17 . . . 121.00 no
    N4 C18 H18 . . . 118.00 no
    C17 C18 H18 . . . 118.00 no
    N4 C19 H19 . . . 119.00 no
    C20 C19 H19 . . . 119.00 no
    C16 C20 H20 . . . 121.00 no
    C19 C20 H20 . . . 121.00 no
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 N1 C13 C12 . . . . -0.1(5) no
    C13 N1 C14 C15 . . . . 0.7(5) no
    C11 N2 N3 C16 . . . . 178.0(3) no
    N3 N2 C11 C15 . . . . 166.5(3) no
    N3 N2 C11 C12 . . . . -17.0(5) no
    N2 N3 C16 C17 . . . . -178.4(3) no
    N2 N3 C16 C20 . . . . -0.6(5) no
    C19 N4 C18 C17 . . . . 0.8(8) no
    C18 N4 C19 C20 . . . . -1.9(9) no
    C9 C1 C2 C3 . . . . 0.3(4) no
    C8 C1 C2 C3 . . . . 179.4(3) no
    C8 C1 C2 C5 . . . . -0.7(4) no
    C2 C1 C8 C7 . . . . 0.6(5) no
    C9 C1 C8 C7 . . . . 179.7(3) no
    C9 C1 C2 C5 . . . . -179.8(3) no
    C1 C2 C3 C2 . . . 2_555 -179.5(2) no
    C1 C2 C5 C4 . . . . 178.9(2) no
    C1 C2 C5 C6 . . . . 0.3(4) no
    C5 C2 C3 C2 . . . 2_555 0.6(3) no
    C3 C2 C5 C6 . . . . -179.8(2) no
    C3 C2 C5 C4 . . . . -1.2(4) no
    C5 C4 C5 C6 2_555 . . . 179.2(3) no
    C5 C4 C5 C2 2_555 . . . 0.6(3) no
    C2 C5 C6 C7 . . . . 0.3(5) no
    C4 C5 C6 C7 . . . . -178.3(3) no
    C5 C6 C7 C8 . . . . -0.4(5) no
    C6 C7 C8 C1 . . . . -0.1(5) no
    N2 C11 C12 C13 . . . . -176.9(3) no
    C15 C11 C12 C13 . . . . -0.6(5) no
    N2 C11 C15 C14 . . . . 177.8(3) no
    C12 C11 C15 C14 . . . . 1.1(5) no
    C11 C12 C13 N1 . . . . 0.0(5) no
    N1 C14 C15 C11 . . . . -1.2(5) no
    N3 C16 C17 C18 . . . . 177.3(4) no
    C20 C16 C17 C18 . . . . -0.6(6) no
    N3 C16 C20 C19 . . . . -178.2(4) no
    C17 C16 C20 C19 . . . . -0.5(7) no
    C16 C17 C18 N4 . . . . 0.5(7) no
    N4 C19 C20 C16 . . . . 1.8(9) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    C13 H13 I1 4_565 0.93 3.30 4.131(3) 150.4
    C14 H14 I1 4_564 0.93 3.31 4.160(4) 153.1
data_DIEABipyNO
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2016-08-25
_journal_date_accepted     2016-10-15
_journal_name_full     'Acta Crystallographica, Section B'
_journal_year     2017
_journal_volume     73
_journal_issue      2
_journal_page_first     163
_journal_page_last     167
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2052520616016450
_journal_coeditor_code     AO5017
_database_code_depnum_ccdc_archive     'CCDC 1483702'
_chemical_name_systematic
;
TW-10-45 1,8-di(iodoethynyl)anthracene, (4,4'-bipyridyl-1-oxide)2
;
_chemical_name_common     ?
_chemical_formula_moiety
;
(C18 H8 I2) (C10 H8 N2 O)2
;
_chemical_formula_sum     'C38 H24 I2 N4 O2'
_chemical_formula_weight     822.41
_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     9.6027(18)
_cell_length_b     10.0523(19)
_cell_length_c     18.021(4)
_cell_angle_alpha     85.600(5)
_cell_angle_beta     80.043(5)
_cell_angle_gamma     68.603(5)
_cell_volume     1595.0(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9981
_cell_measurement_theta_min     2.30
_cell_measurement_theta_max     32.58
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.300
_exptl_crystal_size_mid     0.240
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.712
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     804
_exptl_absorpt_coefficient_mu     2.013
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS'
_shelx_estimated_absorpt_T_min     0.583
_shelx_estimated_absorpt_T_max     0.766
_exptl_absorpt_correction_T_min     0.592
_exptl_absorpt_correction_T_max     0.766
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEX-II CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     45988
_diffrn_reflns_av_R_equivalents     0.0362
_diffrn_reflns_theta_min     2.176
_diffrn_reflns_theta_max     32.663
_diffrn_reflns_theta_full     30.000
_diffrn_measured_fraction_theta_max     0.932
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_refine_special_details
;
 ?
;
_reflns_number_total     10925
_reflns_number_gt     10024
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0411
_refine_ls_R_factor_gt     0.0375
_refine_ls_wR_factor_gt     0.0929
_refine_ls_wR_factor_ref     0.0948
_refine_ls_goodness_of_fit_ref     1.129
_refine_ls_restrained_S_all     1.129
_refine_ls_number_reflns     10925
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0300P)²+3.5000P] 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     1.946
_refine_diff_density_min     -1.383
_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'
    'O' 'O' 0.0106 0.0060
                         '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     'Bruker APEX2'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement     'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material     'Bruker SHELXTL'
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
    C C11 0.7590(3) 0.2928(3) 0.15396(15) 0.0222(4) Uani d 1 . .
    C C12 0.6999(3) 0.4466(3) 0.14743(15) 0.0237(5) Uani d 1 . .
    C C13 0.6640(3) 0.5109(3) 0.07985(16) 0.0289(5) Uani d 1 . .
    H H13 0.6240 0.6121 0.0759 0.035 Uiso calc 1 . .
    C C14 0.6859(4) 0.4278(3) 0.01612(17) 0.0308(6) Uani d 1 . .
    H H14 0.6614 0.4742 -0.0303 0.037 Uiso calc 1 . .
    C C15 0.7417(3) 0.2823(3) 0.02010(16) 0.0281(5) Uani d 1 . .
    H H15 0.7554 0.2284 -0.0234 0.034 Uiso calc 1 . .
    C C16 0.7794(3) 0.2108(3) 0.08902(15) 0.0234(5) Uani d 1 . .
    C C17 0.8364(3) 0.0615(3) 0.09482(15) 0.0257(5) Uani d 1 . .
    H H17 0.8502 0.0063 0.0518 0.031 Uiso calc 1 . .
    C C18 0.8730(3) -0.0074(3) 0.16268(16) 0.0241(5) Uani d 1 . .
    C C19 0.9262(3) -0.1600(3) 0.16951(17) 0.0281(5) Uani d 1 . .
    H H19 0.9393 -0.2159 0.1269 0.034 Uiso calc 1 . .
    C C20 0.9578(4) -0.2249(3) 0.23657(18) 0.0316(6) Uani d 1 . .
    H H20 0.9913 -0.3262 0.2405 0.038 Uiso calc 1 . .
    C C21 0.9416(3) -0.1447(3) 0.30072(17) 0.0293(5) Uani d 1 . .
    H H21 0.9658 -0.1929 0.3468 0.035 Uiso calc 1 . .
    C C22 0.8915(3) 0.0023(3) 0.29726(15) 0.0244(5) Uani d 1 . .
    C C23 0.8538(3) 0.0750(3) 0.22734(15) 0.0219(4) Uani d 1 . .
    C C24 0.7975(3) 0.2221(3) 0.22171(15) 0.0231(5) Uani d 1 . .
    H H24 0.7846 0.2769 0.2648 0.028 Uiso calc 1 . .
    C C31 0.6809(3) 0.5278(3) 0.21282(16) 0.0256(5) Uani d 1 . .
    C C32 0.6709(3) 0.5827(3) 0.27121(16) 0.0276(5) Uani d 1 . .
    I I1 0.64725(2) 0.67094(2) 0.37201(2) 0.02641(5) Uani d 1 . .
    C C41 0.8771(3) 0.0835(3) 0.36170(16) 0.0258(5) Uani d 1 . .
    C C42 0.8657(3) 0.1561(3) 0.41419(16) 0.0282(5) Uani d 1 . .
    I I2 0.83599(2) 0.28213(2) 0.50214(2) 0.02591(5) Uani d 1 . .
    N N51 0.6204(3) 0.7932(3) 0.50511(15) 0.0323(5) Uani d 1 . .
    C C52 0.5334(3) 0.7748(3) 0.56815(18) 0.0314(6) Uani d 1 . .
    H H52 0.4751 0.7167 0.5666 0.038 Uiso calc 1 . .
    C C53 0.5242(3) 0.8366(3) 0.63581(16) 0.0260(5) Uani d 1 . .
    H H53 0.4589 0.8226 0.6792 0.031 Uiso calc 1 . .
    C C54 0.6119(3) 0.9195(3) 0.63965(15) 0.0221(4) Uani d 1 . .
    C C55 0.7025(4) 0.9375(3) 0.57377(17) 0.0310(6) Uani d 1 . .
    H H55 0.7643 0.9929 0.5736 0.037 Uiso calc 1 . .
    C C56 0.7021(4) 0.8744(4) 0.50860(17) 0.0346(6) Uani d 1 . .
    H H56 0.7632 0.8896 0.4638 0.042 Uiso calc 1 . .
    N N61 0.6083(3) 1.1010(3) 0.84562(17) 0.0373(6) Uani d 1 . .
    O O61 0.6095(3) 1.1547(4) 0.90834(17) 0.0599(9) Uani d 1 . .
    C C62 0.4805(3) 1.0890(3) 0.83063(17) 0.0292(5) Uani d 1 . .
    H H62 0.3899 1.1218 0.8660 0.035 Uiso calc 1 . .
    C C63 0.4808(3) 1.0297(3) 0.76443(15) 0.0242(5) Uani d 1 . .
    H H63 0.3905 1.0202 0.7552 0.029 Uiso calc 1 . .
    C C64 0.6103(3) 0.9832(3) 0.71063(15) 0.0237(5) Uani d 1 . .
    C C65 0.7393(3) 0.9986(4) 0.7281(2) 0.0370(7) Uani d 1 . .
    H H65 0.8304 0.9690 0.6930 0.044 Uiso calc 1 . .
    C C66 0.7368(4) 1.0556(5) 0.7950(2) 0.0465(9) Uani d 1 . .
    H H66 0.8266 1.0635 0.8061 0.056 Uiso calc 1 . .
    N N71 0.7946(3) 0.4552(3) 0.62311(15) 0.0324(5) Uani d 1 . .
    C C72 0.6926(4) 0.4527(4) 0.68331(19) 0.0364(7) Uani d 1 . .
    H H72 0.6267 0.4029 0.6800 0.044 Uiso calc 1 . .
    C C73 0.6780(3) 0.5190(4) 0.75021(17) 0.0314(6) Uani d 1 . .
    H H73 0.6023 0.5160 0.7912 0.038 Uiso calc 1 . .
    C C74 0.7751(3) 0.5898(3) 0.75690(16) 0.0253(5) Uani d 1 . .
    C C75 0.8801(3) 0.5941(3) 0.69374(17) 0.0292(5) Uani d 1 . .
    H H75 0.9475 0.6431 0.6951 0.035 Uiso calc 1 . .
    C C76 0.8849(3) 0.5259(3) 0.62888(17) 0.0292(5) Uani d 1 . .
    H H76 0.9569 0.5300 0.5862 0.035 Uiso calc 1 . .
    N N81 0.7767(4) 0.7554(4) 0.96622(16) 0.0399(6) Uani d 1 . .
    O O81 0.7813(4) 0.8005(4) 1.03040(16) 0.0539(8) Uani d 1 . .
    C C82 0.6420(4) 0.7807(4) 0.94229(18) 0.0348(6) Uani d 1 . .
    H H82 0.5500 0.8351 0.9724 0.042 Uiso calc 1 . .
    C C83 0.6386(3) 0.7277(3) 0.87486(17) 0.0303(6) Uani d 1 . .
    H H83 0.5440 0.7439 0.8594 0.036 Uiso calc 1 . .
    C C84 0.7729(3) 0.6504(3) 0.82874(16) 0.0276(5) Uani d 1 . .
    C C85 0.9084(4) 0.6282(4) 0.8553(2) 0.0384(7) Uani d 1 . .
    H H85 1.0023 0.5770 0.8255 0.046 Uiso calc 1 . .
    C C86 0.9075(4) 0.6794(5) 0.9237(2) 0.0443(8) Uani d 1 . .
    H H86 1.0005 0.6609 0.9414 0.053 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
    C11 C24 . 1.401(4) ?
    C11 C16 . 1.427(4) ?
    C11 C12 . 1.443(4) ?
    C12 C13 . 1.372(4) ?
    C12 C31 . 1.433(4) ?
    C13 C14 . 1.412(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.363(4) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.421(4) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.400(4) ?
    C17 C18 . 1.393(4) ?
    C17 H17 . 0.9500 ?
    C18 C23 . 1.428(4) ?
    C18 C19 . 1.432(4) ?
    C19 C20 . 1.356(4) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.415(4) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.377(4) ?
    C21 H21 . 0.9500 ?
    C22 C41 . 1.429(4) ?
    C22 C23 . 1.441(4) ?
    C23 C24 . 1.380(4) ?
    C24 H24 . 0.9500 ?
    C31 C32 . 1.199(4) ?
    C32 I1 . 2.023(3) ?
    I1 N51 . 2.709(3) ?
    C41 C42 . 1.205(4) ?
    C42 I2 . 2.021(3) ?
    I2 N71 . 2.778(3) ?
    N51 C52 . 1.332(4) ?
    N51 C56 . 1.333(4) ?
    C52 C53 . 1.385(4) ?
    C52 H52 . 0.9500 ?
    C53 C54 . 1.396(4) ?
    C53 H53 . 0.9500 ?
    C54 C55 . 1.387(4) ?
    C54 C64 . 1.469(4) ?
    C55 C56 . 1.378(4) ?
    C55 H55 . 0.9500 ?
    C56 H56 . 0.9500 ?
    N61 O61 . 1.293(3) ?
    N61 C62 . 1.349(4) ?
    N61 C66 . 1.352(4) ?
    C62 C63 . 1.373(4) ?
    C62 H62 . 0.9500 ?
    C63 C64 . 1.391(4) ?
    C63 H63 . 0.9500 ?
    C64 C65 . 1.393(4) ?
    C65 C66 . 1.366(4) ?
    C65 H65 . 0.9500 ?
    C66 H66 . 0.9500 ?
    N71 C76 . 1.327(4) ?
    N71 C72 . 1.335(4) ?
    C72 C73 . 1.383(4) ?
    C72 H72 . 0.9500 ?
    C73 C74 . 1.389(4) ?
    C73 H73 . 0.9500 ?
    C74 C75 . 1.393(4) ?
    C74 C84 . 1.466(4) ?
    C75 C76 . 1.385(4) ?
    C75 H75 . 0.9500 ?
    C76 H76 . 0.9500 ?
    N81 O81 . 1.288(4) ?
    N81 C86 . 1.343(5) ?
    N81 C82 . 1.364(5) ?
    C82 C83 . 1.373(4) ?
    C82 H82 . 0.9500 ?
    C83 C84 . 1.398(4) ?
    C83 H83 . 0.9500 ?
    C84 C85 . 1.400(4) ?
    C85 C86 . 1.369(5) ?
    C85 H85 . 0.9500 ?
    C86 H86 . 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
    C24 C11 C16 . . 119.4(2) ?
    C24 C11 C12 . . 122.0(2) ?
    C16 C11 C12 . . 118.6(2) ?
    C13 C12 C31 . . 121.9(3) ?
    C13 C12 C11 . . 119.9(2) ?
    C31 C12 C11 . . 118.2(2) ?
    C12 C13 C14 . . 120.6(3) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C15 C14 C13 . . 121.2(3) ?
    C15 C14 H14 . . 119.4 ?
    C13 C14 H14 . . 119.4 ?
    C14 C15 C16 . . 120.3(3) ?
    C14 C15 H15 . . 119.9 ?
    C16 C15 H15 . . 119.9 ?
    C17 C16 C15 . . 121.5(2) ?
    C17 C16 C11 . . 119.1(2) ?
    C15 C16 C11 . . 119.4(3) ?
    C18 C17 C16 . . 121.0(2) ?
    C18 C17 H17 . . 119.5 ?
    C16 C17 H17 . . 119.5 ?
    C17 C18 C23 . . 119.8(2) ?
    C17 C18 C19 . . 121.2(2) ?
    C23 C18 C19 . . 119.1(3) ?
    C20 C19 C18 . . 120.3(3) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 121.2(3) ?
    C19 C20 H20 . . 119.4 ?
    C21 C20 H20 . . 119.4 ?
    C22 C21 C20 . . 121.0(3) ?
    C22 C21 H21 . . 119.5 ?
    C20 C21 H21 . . 119.5 ?
    C21 C22 C41 . . 121.1(3) ?
    C21 C22 C23 . . 119.3(2) ?
    C41 C22 C23 . . 119.6(2) ?
    C24 C23 C18 . . 119.3(2) ?
    C24 C23 C22 . . 121.6(2) ?
    C18 C23 C22 . . 119.2(2) ?
    C23 C24 C11 . . 121.5(2) ?
    C23 C24 H24 . . 119.2 ?
    C11 C24 H24 . . 119.2 ?
    C32 C31 C12 . . 173.3(3) ?
    C31 C32 I1 . . 177.3(3) ?
    C32 I1 N51 . . 178.39(11) ?
    C42 C41 C22 . . 177.5(3) ?
    C41 C42 I2 . . 177.3(3) ?
    C42 I2 N71 . . 179.87(11) ?
    C52 N51 C56 . . 117.5(3) ?
    C52 N51 I1 . . 124.3(2) ?
    C56 N51 I1 . . 118.2(2) ?
    N51 C52 C53 . . 123.0(3) ?
    N51 C52 H52 . . 118.5 ?
    C53 C52 H52 . . 118.5 ?
    C52 C53 C54 . . 119.4(3) ?
    C52 C53 H53 . . 120.3 ?
    C54 C53 H53 . . 120.3 ?
    C55 C54 C53 . . 117.2(2) ?
    C55 C54 C64 . . 121.3(2) ?
    C53 C54 C64 . . 121.6(2) ?
    C56 C55 C54 . . 119.4(3) ?
    C56 C55 H55 . . 120.3 ?
    C54 C55 H55 . . 120.3 ?
    N51 C56 C55 . . 123.5(3) ?
    N51 C56 H56 . . 118.3 ?
    C55 C56 H56 . . 118.3 ?
    O61 N61 C62 . . 120.6(3) ?
    O61 N61 C66 . . 119.4(3) ?
    C62 N61 C66 . . 119.9(3) ?
    N61 C62 C63 . . 120.2(3) ?
    N61 C62 H62 . . 119.9 ?
    C63 C62 H62 . . 119.9 ?
    C62 C63 C64 . . 121.5(3) ?
    C62 C63 H63 . . 119.2 ?
    C64 C63 H63 . . 119.2 ?
    C63 C64 C65 . . 116.3(2) ?
    C63 C64 C54 . . 121.9(2) ?
    C65 C64 C54 . . 121.7(2) ?
    C66 C65 C64 . . 121.1(3) ?
    C66 C65 H65 . . 119.5 ?
    C64 C65 H65 . . 119.5 ?
    N61 C66 C65 . . 120.9(3) ?
    N61 C66 H66 . . 119.5 ?
    C65 C66 H66 . . 119.5 ?
    C76 N71 C72 . . 117.3(3) ?
    C76 N71 I2 . . 123.2(2) ?
    C72 N71 I2 . . 118.8(2) ?
    N71 C72 C73 . . 123.3(3) ?
    N71 C72 H72 . . 118.3 ?
    C73 C72 H72 . . 118.3 ?
    C72 C73 C74 . . 119.4(3) ?
    C72 C73 H73 . . 120.3 ?
    C74 C73 H73 . . 120.3 ?
    C73 C74 C75 . . 117.2(3) ?
    C73 C74 C84 . . 121.2(3) ?
    C75 C74 C84 . . 121.4(3) ?
    C76 C75 C74 . . 119.1(3) ?
    C76 C75 H75 . . 120.4 ?
    C74 C75 H75 . . 120.4 ?
    N71 C76 C75 . . 123.6(3) ?
    N71 C76 H76 . . 118.2 ?
    C75 C76 H76 . . 118.2 ?
    O81 N81 C86 . . 118.7(3) ?
    O81 N81 C82 . . 121.0(3) ?
    C86 N81 C82 . . 120.3(3) ?
    N81 C82 C83 . . 120.4(3) ?
    N81 C82 H82 . . 119.8 ?
    C83 C82 H82 . . 119.8 ?
    C82 C83 C84 . . 120.7(3) ?
    C82 C83 H83 . . 119.6 ?
    C84 C83 H83 . . 119.6 ?
    C83 C84 C85 . . 116.9(3) ?
    C83 C84 C74 . . 122.8(3) ?
    C85 C84 C74 . . 120.3(3) ?
    C86 C85 C84 . . 120.9(3) ?
    C86 C85 H85 . . 119.6 ?
    C84 C85 H85 . . 119.6 ?
    N81 C86 C85 . . 120.9(3) ?
    N81 C86 H86 . . 119.6 ?
    C85 C86 H86 . . 119.6 ?
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
    C24 C11 C12 C13 . . . . 179.9(3) ?
    C16 C11 C12 C13 . . . . 0.3(4) ?
    C24 C11 C12 C31 . . . . 0.1(4) ?
    C16 C11 C12 C31 . . . . -179.6(2) ?
    C31 C12 C13 C14 . . . . 179.1(3) ?
    C11 C12 C13 C14 . . . . -0.7(4) ?
    C12 C13 C14 C15 . . . . 0.7(5) ?
    C13 C14 C15 C16 . . . . -0.1(5) ?
    C14 C15 C16 C17 . . . . 179.7(3) ?
    C14 C15 C16 C11 . . . . -0.3(4) ?
    C24 C11 C16 C17 . . . . 0.5(4) ?
    C12 C11 C16 C17 . . . . -179.8(2) ?
    C24 C11 C16 C15 . . . . -179.4(2) ?
    C12 C11 C16 C15 . . . . 0.2(4) ?
    C15 C16 C17 C18 . . . . 180.0(3) ?
    C11 C16 C17 C18 . . . . 0.0(4) ?
    C16 C17 C18 C23 . . . . -0.6(4) ?
    C16 C17 C18 C19 . . . . 177.7(3) ?
    C17 C18 C19 C20 . . . . -178.4(3) ?
    C23 C18 C19 C20 . . . . -0.1(4) ?
    C18 C19 C20 C21 . . . . -1.0(5) ?
    C19 C20 C21 C22 . . . . 0.8(5) ?
    C20 C21 C22 C41 . . . . -179.1(3) ?
    C20 C21 C22 C23 . . . . 0.6(4) ?
    C17 C18 C23 C24 . . . . 0.6(4) ?
    C19 C18 C23 C24 . . . . -177.7(2) ?
    C17 C18 C23 C22 . . . . 179.7(2) ?
    C19 C18 C23 C22 . . . . 1.4(4) ?
    C21 C22 C23 C24 . . . . 177.4(3) ?
    C41 C22 C23 C24 . . . . -2.8(4) ?
    C21 C22 C23 C18 . . . . -1.6(4) ?
    C41 C22 C23 C18 . . . . 178.1(2) ?
    C18 C23 C24 C11 . . . . -0.1(4) ?
    C22 C23 C24 C11 . . . . -179.2(2) ?
    C16 C11 C24 C23 . . . . -0.5(4) ?
    C12 C11 C24 C23 . . . . 179.9(2) ?
    C56 N51 C52 C53 . . . . 0.4(5) ?
    I1 N51 C52 C53 . . . . 178.7(2) ?
    N51 C52 C53 C54 . . . . -1.5(5) ?
    C52 C53 C54 C55 . . . . 1.2(4) ?
    C52 C53 C54 C64 . . . . -177.8(3) ?
    C53 C54 C55 C56 . . . . 0.1(4) ?
    C64 C54 C55 C56 . . . . 179.2(3) ?
    C52 N51 C56 C55 . . . . 1.1(5) ?
    I1 N51 C56 C55 . . . . -177.4(3) ?
    C54 C55 C56 N51 . . . . -1.3(5) ?
    O61 N61 C62 C63 . . . . -178.9(3) ?
    C66 N61 C62 C63 . . . . 0.6(5) ?
    N61 C62 C63 C64 . . . . -1.3(5) ?
    C62 C63 C64 C65 . . . . 0.8(4) ?
    C62 C63 C64 C54 . . . . 180.0(3) ?
    C55 C54 C64 C63 . . . . 147.6(3) ?
    C53 C54 C64 C63 . . . . -33.5(4) ?
    C55 C54 C64 C65 . . . . -33.3(4) ?
    C53 C54 C64 C65 . . . . 145.7(3) ?
    C63 C64 C65 C66 . . . . 0.4(5) ?
    C54 C64 C65 C66 . . . . -178.8(4) ?
    O61 N61 C66 C65 . . . . -179.9(4) ?
    C62 N61 C66 C65 . . . . 0.6(6) ?
    C64 C65 C66 N61 . . . . -1.1(7) ?
    C76 N71 C72 C73 . . . . -0.3(5) ?
    I2 N71 C72 C73 . . . . 170.7(3) ?
    N71 C72 C73 C74 . . . . -1.3(5) ?
    C72 C73 C74 C75 . . . . 2.1(5) ?
    C72 C73 C74 C84 . . . . -174.5(3) ?
    C73 C74 C75 C76 . . . . -1.4(4) ?
    C84 C74 C75 C76 . . . . 175.2(3) ?
    C72 N71 C76 C75 . . . . 1.1(5) ?
    I2 N71 C76 C75 . . . . -169.5(2) ?
    C74 C75 C76 N71 . . . . -0.2(5) ?
    O81 N81 C82 C83 . . . . -177.8(3) ?
    C86 N81 C82 C83 . . . . 0.5(5) ?
    N81 C82 C83 C84 . . . . -1.7(5) ?
    C82 C83 C84 C85 . . . . 1.1(5) ?
    C82 C83 C84 C74 . . . . 179.0(3) ?
    C73 C74 C84 C83 . . . . -44.0(4) ?
    C75 C74 C84 C83 . . . . 139.6(3) ?
    C73 C74 C84 C85 . . . . 133.8(3) ?
    C75 C74 C84 C85 . . . . -42.6(4) ?
    C83 C84 C85 C86 . . . . 0.6(5) ?
    C74 C84 C85 C86 . . . . -177.3(3) ?
    O81 N81 C86 C85 . . . . 179.5(4) ?
    C82 N81 C86 C85 . . . . 1.2(6) ?
    C84 C85 C86 N81 . . . . -1.8(6) ?
_shelxl_version_number     .2013
data_DIEABpe
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 1483703'
_chemical_name_systematic
;
TW-10-14 1,8-di(iodoethynyl)anthracene, 1,2-bis(4-pyridyl)ethane
;
_chemical_name_common     ?
_chemical_formula_moiety
;
(C18 H8 I2) (C12 H12 N2)
;
_chemical_formula_sum     'C30 H20 I2 N2'
_chemical_formula_weight     662.28
_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     9.5153(16)
_cell_length_b     9.6261(16)
_cell_length_c     14.368(3)
_cell_angle_alpha     96.346(5)
_cell_angle_beta     93.215(5)
_cell_angle_gamma     103.295(4)
_cell_volume     1268.4(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9607
_cell_measurement_theta_min     2.21
_cell_measurement_theta_max     32.45
_cell_measurement_temperature     120(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     bronze
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.280
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.734
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     640
_exptl_absorpt_coefficient_mu     2.500
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS'
_shelx_estimated_absorpt_T_min     0.435
_shelx_estimated_absorpt_T_max     0.721
_exptl_absorpt_correction_T_min     0.595
_exptl_absorpt_correction_T_max     0.721
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEX-II CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     38542
_diffrn_reflns_av_R_equivalents     0.0318
_diffrn_reflns_theta_min     2.192
_diffrn_reflns_theta_max     32.488
_diffrn_reflns_theta_full     30.000
_diffrn_measured_fraction_theta_max     0.928
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
 ?
;
_reflns_number_total     8522
_reflns_number_gt     7891
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0279
_refine_ls_R_factor_gt     0.0254
_refine_ls_wR_factor_gt     0.0660
_refine_ls_wR_factor_ref     0.0674
_refine_ls_goodness_of_fit_ref     1.071
_refine_ls_restrained_S_all     1.071
_refine_ls_number_reflns     8522
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0300P)²+1.0000P] 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     1.484
_refine_diff_density_min     -0.845
_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     'Bruker APEX2'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement     'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material     'Bruker SHELXTL'
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
    C C11 0.51557(19) -0.08715(19) 0.39395(12) 0.0216(3) Uani d 1 . .
    C C12 0.6412(2) 0.0273(2) 0.38789(12) 0.0235(3) Uani d 1 . .
    C C13 0.7757(2) 0.0183(2) 0.42377(14) 0.0281(4) Uani d 1 . .
    H H13 0.8579 0.0941 0.4195 0.034 Uiso calc 1 . .
    C C14 0.7926(2) -0.1029(2) 0.46702(15) 0.0313(4) Uani d 1 . .
    H H14 0.8859 -0.1069 0.4922 0.038 Uiso calc 1 . .
    C C15 0.6769(2) -0.2133(2) 0.47287(14) 0.0304(4) Uani d 1 . .
    H H15 0.6905 -0.2941 0.5015 0.036 Uiso calc 1 . .
    C C16 0.5348(2) -0.2100(2) 0.43662(13) 0.0251(3) Uani d 1 . .
    C C17 0.4150(2) -0.3220(2) 0.44240(14) 0.0273(4) Uani d 1 . .
    H H17 0.4282 -0.4039 0.4700 0.033 Uiso calc 1 . .
    C C18 0.2760(2) -0.31717(19) 0.40873(13) 0.0244(3) Uani d 1 . .
    C C19 0.1523(2) -0.4314(2) 0.41500(14) 0.0291(4) Uani d 1 . .
    H H19 0.1644 -0.5139 0.4422 0.035 Uiso calc 1 . .
    C C20 0.0175(2) -0.4239(2) 0.38256(15) 0.0298(4) Uani d 1 . .
    H H20 -0.0633 -0.5015 0.3867 0.036 Uiso calc 1 . .
    C C21 -0.0033(2) -0.3015(2) 0.34285(14) 0.0273(3) Uani d 1 . .
    H H21 -0.0982 -0.2979 0.3206 0.033 Uiso calc 1 . .
    C C22 0.1117(2) -0.18721(19) 0.33584(13) 0.0234(3) Uani d 1 . .
    C C23 0.25642(19) -0.19285(18) 0.36762(12) 0.0216(3) Uani d 1 . .
    C C24 0.37687(19) -0.08126(19) 0.36047(12) 0.0220(3) Uani d 1 . .
    H H24 0.3641 0.0002 0.3323 0.026 Uiso calc 1 . .
    C C31 0.6273(2) 0.1492(2) 0.34253(13) 0.0251(3) Uani d 1 . .
    C C32 0.6185(2) 0.2497(2) 0.30121(14) 0.0278(4) Uani d 1 . .
    I I1 0.61962(2) 0.41887(2) 0.22996(2) 0.02785(4) Uani d 1 . .
    C C41 0.0904(2) -0.0613(2) 0.29833(13) 0.0248(3) Uani d 1 . .
    C C42 0.0806(2) 0.0495(2) 0.26973(14) 0.0275(3) Uani d 1 . .
    I I2 0.07998(2) 0.23912(2) 0.22174(2) 0.02796(4) Uani d 1 . .
    N N51 0.6470(2) 0.66039(19) 0.13306(13) 0.0324(4) Uani d 1 . .
    C C52 0.6391(2) 0.6643(2) 0.04022(16) 0.0352(4) Uani d 1 . .
    H H52 0.6189 0.5758 -0.0002 0.042 Uiso calc 1 . .
    C C53 0.6589(2) 0.7913(3) 0.00002(15) 0.0351(4) Uani d 1 . .
    H H53 0.6515 0.7886 -0.0664 0.042 Uiso calc 1 . .
    C C54 0.6896(2) 0.9218(2) 0.05726(15) 0.0311(4) Uani d 1 . .
    C C55 0.7006(2) 0.9175(2) 0.15287(15) 0.0304(4) Uani d 1 . .
    H H55 0.7238 1.0044 0.1950 0.037 Uiso calc 1 . .
    C C56 0.6779(2) 0.7871(2) 0.18713(14) 0.0307(4) Uani d 1 . .
    H H56 0.6846 0.7872 0.2534 0.037 Uiso calc 1 . .
    C C57 0.7144(3) 1.0671(3) 0.0218(2) 0.0470(6) Uani d 1 . .
    H H57A 0.6192 1.0836 0.0012 0.056 Uiso calc 1 . .
    H H57B 0.7580 1.1423 0.0748 0.056 Uiso calc 1 . .
    N N61 0.8927(2) 1.50111(19) -0.15155(13) 0.0319(4) Uani d 1 . .
    C C62 0.9984(3) 1.4471(2) -0.11592(16) 0.0361(4) Uani d 1 . .
    H H62 1.0952 1.5031 -0.1121 0.043 Uiso calc 1 . .
    C C63 0.9737(3) 1.3136(3) -0.08434(17) 0.0395(5) Uani d 1 . .
    H H63 1.0527 1.2794 -0.0603 0.047 Uiso calc 1 . .
    C C64 0.8349(3) 1.2307(2) -0.08775(18) 0.0405(5) Uani d 1 . .
    C C65 0.7244(3) 1.2865(2) -0.12439(18) 0.0394(5) Uani d 1 . .
    H H65 0.6266 1.2331 -0.1281 0.047 Uiso calc 1 . .
    C C66 0.7576(3) 1.4201(2) -0.15542(16) 0.0347(4) Uani d 1 . .
    H H66 0.6807 1.4561 -0.1807 0.042 Uiso calc 1 . .
    C C67 0.8063(4) 1.0846(3) -0.0550(3) 0.0743(12) Uani d 1 . .
    H H67A 0.7608 1.0118 -0.1088 0.089 Uiso calc 1 . .
    H H67B 0.9003 1.0647 -0.0353 0.089 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
    C11 C24 . 1.395(2) ?
    C11 C16 . 1.434(2) ?
    C11 C12 . 1.441(3) ?
    C12 C13 . 1.377(3) ?
    C12 C31 . 1.432(3) ?
    C13 C14 . 1.417(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.357(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.430(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.390(3) ?
    C17 C18 . 1.396(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.428(3) ?
    C18 C23 . 1.436(2) ?
    C19 C20 . 1.361(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.412(3) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.379(3) ?
    C21 H21 . 0.9500 ?
    C22 C41 . 1.430(2) ?
    C22 C23 . 1.441(2) ?
    C23 C24 . 1.396(3) ?
    C24 H24 . 0.9500 ?
    C31 C32 . 1.206(3) ?
    C32 I1 . 2.016(2) ?
    I1 N51 . 2.8088(18) ?
    C41 C42 . 1.206(3) ?
    C42 I2 . 2.0219(19) ?
    N51 C56 . 1.333(3) ?
    N51 C52 . 1.337(3) ?
    C52 C53 . 1.387(3) ?
    C52 H52 . 0.9500 ?
    C53 C54 . 1.384(3) ?
    C53 H53 . 0.9500 ?
    C54 C55 . 1.378(3) ?
    C54 C57 . 1.513(3) ?
    C55 C56 . 1.375(3) ?
    C55 H55 . 0.9500 ?
    C56 H56 . 0.9500 ?
    C57 C67 . 1.446(4) ?
    C57 H57A . 0.9900 ?
    C57 H57B . 0.9900 ?
    N61 C66 . 1.336(3) ?
    N61 C62 . 1.336(3) ?
    N61 I2 2_675 2.7614(17) ?
    C62 C63 . 1.384(3) ?
    C62 H62 . 0.9500 ?
    C63 C64 . 1.372(4) ?
    C63 H63 . 0.9500 ?
    C64 C65 . 1.390(4) ?
    C64 C67 . 1.502(3) ?
    C65 C66 . 1.381(3) ?
    C65 H65 . 0.9500 ?
    C66 H66 . 0.9500 ?
    C67 H67A . 0.9900 ?
    C67 H67B . 0.9900 ?
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
    C24 C11 C16 . . 119.39(17) ?
    C24 C11 C12 . . 122.15(16) ?
    C16 C11 C12 . . 118.46(16) ?
    C13 C12 C31 . . 119.71(18) ?
    C13 C12 C11 . . 120.15(17) ?
    C31 C12 C11 . . 120.12(16) ?
    C12 C13 C14 . . 120.74(19) ?
    C12 C13 H13 . . 119.6 ?
    C14 C13 H13 . . 119.6 ?
    C15 C14 C13 . . 120.60(18) ?
    C15 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.7 ?
    C14 C15 C16 . . 121.11(18) ?
    C14 C15 H15 . . 119.4 ?
    C16 C15 H15 . . 119.4 ?
    C17 C16 C15 . . 121.79(17) ?
    C17 C16 C11 . . 119.28(17) ?
    C15 C16 C11 . . 118.92(18) ?
    C16 C17 C18 . . 121.67(17) ?
    C16 C17 H17 . . 119.2 ?
    C18 C17 H17 . . 119.2 ?
    C17 C18 C19 . . 121.97(17) ?
    C17 C18 C23 . . 119.01(17) ?
    C19 C18 C23 . . 119.02(17) ?
    C20 C19 C18 . . 121.03(17) ?
    C20 C19 H19 . . 119.5 ?
    C18 C19 H19 . . 119.5 ?
    C19 C20 C21 . . 120.46(18) ?
    C19 C20 H20 . . 119.8 ?
    C21 C20 H20 . . 119.8 ?
    C22 C21 C20 . . 121.14(18) ?
    C22 C21 H21 . . 119.4 ?
    C20 C21 H21 . . 119.4 ?
    C21 C22 C41 . . 121.28(17) ?
    C21 C22 C23 . . 119.89(16) ?
    C41 C22 C23 . . 118.83(16) ?
    C24 C23 C18 . . 119.40(16) ?
    C24 C23 C22 . . 122.16(15) ?
    C18 C23 C22 . . 118.44(16) ?
    C11 C24 C23 . . 121.24(16) ?
    C11 C24 H24 . . 119.4 ?
    C23 C24 H24 . . 119.4 ?
    C32 C31 C12 . . 177.2(2) ?
    C31 C32 I1 . . 175.61(17) ?
    C32 I1 N51 . . 175.14(7) ?
    C42 C41 C22 . . 175.9(2) ?
    C41 C42 I2 . . 175.83(17) ?
    C56 N51 C52 . . 116.38(18) ?
    C56 N51 I1 . . 115.29(13) ?
    C52 N51 I1 . . 128.26(14) ?
    N51 C52 C53 . . 123.2(2) ?
    N51 C52 H52 . . 118.4 ?
    C53 C52 H52 . . 118.4 ?
    C54 C53 C52 . . 119.61(19) ?
    C54 C53 H53 . . 120.2 ?
    C52 C53 H53 . . 120.2 ?
    C55 C54 C53 . . 117.03(18) ?
    C55 C54 C57 . . 118.5(2) ?
    C53 C54 C57 . . 124.5(2) ?
    C56 C55 C54 . . 119.76(19) ?
    C56 C55 H55 . . 120.1 ?
    C54 C55 H55 . . 120.1 ?
    N51 C56 C55 . . 123.97(19) ?
    N51 C56 H56 . . 118.0 ?
    C55 C56 H56 . . 118.0 ?
    C67 C57 C54 . . 115.2(2) ?
    C67 C57 H57A . . 108.5 ?
    C54 C57 H57A . . 108.5 ?
    C67 C57 H57B . . 108.5 ?
    C54 C57 H57B . . 108.5 ?
    H57A C57 H57B . . 107.5 ?
    C66 N61 C62 . . 116.91(18) ?
    C66 N61 I2 . 2_675 115.46(14) ?
    C62 N61 I2 . 2_675 127.63(15) ?
    N61 C62 C63 . . 123.3(2) ?
    N61 C62 H62 . . 118.4 ?
    C63 C62 H62 . . 118.4 ?
    C64 C63 C62 . . 119.9(2) ?
    C64 C63 H63 . . 120.1 ?
    C62 C63 H63 . . 120.1 ?
    C63 C64 C65 . . 117.1(2) ?
    C63 C64 C67 . . 120.6(3) ?
    C65 C64 C67 . . 122.2(3) ?
    C66 C65 C64 . . 119.6(2) ?
    C66 C65 H65 . . 120.2 ?
    C64 C65 H65 . . 120.2 ?
    N61 C66 C65 . . 123.2(2) ?
    N61 C66 H66 . . 118.4 ?
    C65 C66 H66 . . 118.4 ?
    C57 C67 C64 . . 115.1(2) ?
    C57 C67 H67A . . 108.5 ?
    C64 C67 H67A . . 108.5 ?
    C57 C67 H67B . . 108.5 ?
    C64 C67 H67B . . 108.5 ?
    H67A C67 H67B . . 107.5 ?
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
    C24 C11 C12 C13 . . . . 178.56(17) ?
    C16 C11 C12 C13 . . . . -0.9(3) ?
    C24 C11 C12 C31 . . . . -2.9(3) ?
    C16 C11 C12 C31 . . . . 177.58(16) ?
    C31 C12 C13 C14 . . . . -178.52(17) ?
    C11 C12 C13 C14 . . . . 0.0(3) ?
    C12 C13 C14 C15 . . . . 0.8(3) ?
    C13 C14 C15 C16 . . . . -0.6(3) ?
    C14 C15 C16 C17 . . . . -179.75(19) ?
    C14 C15 C16 C11 . . . . -0.3(3) ?
    C24 C11 C16 C17 . . . . 1.0(3) ?
    C12 C11 C16 C17 . . . . -179.48(17) ?
    C24 C11 C16 C15 . . . . -178.41(17) ?
    C12 C11 C16 C15 . . . . 1.1(3) ?
    C15 C16 C17 C18 . . . . 178.63(18) ?
    C11 C16 C17 C18 . . . . -0.8(3) ?
    C16 C17 C18 C19 . . . . -179.57(18) ?
    C16 C17 C18 C23 . . . . -0.4(3) ?
    C17 C18 C19 C20 . . . . 179.35(19) ?
    C23 C18 C19 C20 . . . . 0.1(3) ?
    C18 C19 C20 C21 . . . . -0.8(3) ?
    C19 C20 C21 C22 . . . . 0.1(3) ?
    C20 C21 C22 C41 . . . . -178.04(18) ?
    C20 C21 C22 C23 . . . . 1.3(3) ?
    C17 C18 C23 C24 . . . . 1.3(3) ?
    C19 C18 C23 C24 . . . . -179.45(17) ?
    C17 C18 C23 C22 . . . . -178.06(16) ?
    C19 C18 C23 C22 . . . . 1.2(3) ?
    C21 C22 C23 C24 . . . . 178.76(17) ?
    C41 C22 C23 C24 . . . . -1.9(3) ?
    C21 C22 C23 C18 . . . . -1.9(3) ?
    C41 C22 C23 C18 . . . . 177.47(16) ?
    C16 C11 C24 C23 . . . . -0.1(3) ?
    C12 C11 C24 C23 . . . . -179.55(16) ?
    C18 C23 C24 C11 . . . . -1.1(3) ?
    C22 C23 C24 C11 . . . . 178.26(16) ?
    C56 N51 C52 C53 . . . . -1.1(3) ?
    I1 N51 C52 C53 . . . . -177.91(16) ?
    N51 C52 C53 C54 . . . . 0.5(3) ?
    C52 C53 C54 C55 . . . . 0.8(3) ?
    C52 C53 C54 C57 . . . . 179.5(2) ?
    C53 C54 C55 C56 . . . . -1.5(3) ?
    C57 C54 C55 C56 . . . . 179.7(2) ?
    C52 N51 C56 C55 . . . . 0.3(3) ?
    I1 N51 C56 C55 . . . . 177.58(16) ?
    C54 C55 C56 N51 . . . . 1.0(3) ?
    C55 C54 C57 C67 . . . . 134.6(3) ?
    C53 C54 C57 C67 . . . . -44.1(4) ?
    C66 N61 C62 C63 . . . . 0.4(3) ?
    I2 N61 C62 C63 2_675 . . . -178.46(17) ?
    N61 C62 C63 C64 . . . . -0.8(4) ?
    C62 C63 C64 C65 . . . . 0.5(4) ?
    C62 C63 C64 C67 . . . . 179.2(3) ?
    C63 C64 C65 C66 . . . . 0.1(4) ?
    C67 C64 C65 C66 . . . . -178.5(3) ?
    C62 N61 C66 C65 . . . . 0.3(3) ?
    I2 N61 C66 C65 2_675 . . . 179.28(18) ?
    C64 C65 C66 N61 . . . . -0.5(4) ?
    C54 C57 C67 C64 . . . . -178.0(3) ?
    C63 C64 C67 C57 . . . . 119.9(4) ?
    C65 C64 C67 C57 . . . . -61.5(5) ?
_shelxl_version_number     .2013
data_DIEABpen
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 1483704'
_chemical_name_systematic
;
TW-10-15 1,8-di(iodoethynyl)anthracene, 1,2-bis(4-pyridyl)ethylene
;
_chemical_name_common     ?
_chemical_formula_moiety
;
(C18 H8 I2) (C12 H10 N2)
;
_chemical_formula_sum     'C30 H18 I2 N2'
_chemical_formula_weight     660.26
_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     14.4231(12)
_cell_length_b     13.6011(11)
_cell_length_c     13.4798(10)
_cell_angle_alpha     90
_cell_angle_beta     109.397(3)
_cell_angle_gamma     90
_cell_volume     2494.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8149
_cell_measurement_theta_min     2.19
_cell_measurement_theta_max     30.24
_cell_measurement_temperature     120(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.420
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.060
_exptl_crystal_density_diffrn     1.758
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1272
_exptl_absorpt_coefficient_mu     2.543
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS'
_shelx_estimated_absorpt_T_min     0.415
_shelx_estimated_absorpt_T_max     0.862
_exptl_absorpt_correction_T_min     0.485
_exptl_absorpt_correction_T_max     0.862
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEX-II CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     28574
_diffrn_reflns_av_R_equivalents     0.0620
_diffrn_reflns_theta_min     2.117
_diffrn_reflns_theta_max     30.567
_diffrn_reflns_theta_full     30.000
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_refine_special_details
;
 ?
;
_reflns_number_total     7557
_reflns_number_gt     4840
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0949
_refine_ls_R_factor_gt     0.0580
_refine_ls_wR_factor_gt     0.1389
_refine_ls_wR_factor_ref     0.1619
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     7557
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0900P)²] 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     4.195
_refine_diff_density_min     -1.342
_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     'Bruker APEX2'
_computing_cell_refinement     'Bruker SAINT'
_computing_data_reduction     'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement     'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material     'Bruker SHELXTL'
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
    C C11 0.4352(4) 0.3798(4) 0.9798(4) 0.0317(10) Uani d 1 . .
    C C12 0.4634(3) 0.3164(4) 0.9077(4) 0.0308(10) Uani d 1 . .
    C C13 0.5325(4) 0.2456(4) 0.9458(4) 0.0375(11) Uani d 1 . .
    H H13 0.5497 0.2035 0.8984 0.045 Uiso calc 1 . .
    C C14 0.5796(4) 0.2340(4) 1.0564(4) 0.0373(11) Uani d 1 . .
    H H14 0.6277 0.1841 1.0818 0.045 Uiso calc 1 . .
    C C15 0.5564(4) 0.2933(4) 1.1256(4) 0.0351(11) Uani d 1 . .
    H H15 0.5887 0.2845 1.1989 0.042 Uiso calc 1 . .
    C C16 0.4844(4) 0.3682(4) 1.0901(4) 0.0333(11) Uani d 1 . .
    C C17 0.4604(4) 0.4315(4) 1.1594(4) 0.0330(11) Uani d 1 . .
    H H17 0.4944 0.4255 1.2328 0.040 Uiso calc 1 . .
    C C18 0.3884(4) 0.5027(4) 1.1242(4) 0.0320(10) Uani d 1 . .
    C C19 0.3630(4) 0.5666(4) 1.1949(4) 0.0356(11) Uani d 1 . .
    H H19 0.3972 0.5626 1.2683 0.043 Uiso calc 1 . .
    C C20 0.2896(4) 0.6334(4) 1.1568(4) 0.0354(11) Uani d 1 . .
    H H20 0.2721 0.6739 1.2052 0.042 Uiso calc 1 . .
    C C21 0.2384(4) 0.6451(4) 1.0486(4) 0.0390(12) Uani d 1 . .
    H H21 0.1879 0.6930 1.0247 0.047 Uiso calc 1 . .
    C C22 0.2629(4) 0.5854(4) 0.9770(4) 0.0310(10) Uani d 1 . .
    C C23 0.3386(4) 0.5124(3) 1.0133(4) 0.0303(10) Uani d 1 . .
    C C24 0.3645(3) 0.4512(3) 0.9438(3) 0.0287(10) Uani d 1 . .
    H H24 0.3327 0.4589 0.8702 0.034 Uiso calc 1 . .
    C C31 0.4168(4) 0.3305(4) 0.7966(4) 0.0339(11) Uani d 1 . .
    C C32 0.3762(4) 0.3456(4) 0.7040(4) 0.0376(12) Uani d 1 . .
    I I1 0.30702(3) 0.36848(3) 0.54898(2) 0.03563(12) Uani d 1 . .
    C C41 0.2150(4) 0.5969(4) 0.8661(4) 0.0350(11) Uani d 1 . .
    C C42 0.1801(4) 0.6043(4) 0.7715(4) 0.0365(11) Uani d 1 . .
    I I2 0.12471(3) 0.61993(2) 0.61420(3) 0.03521(12) Uani d 1 . .
    N N51 0.2070(4) 0.3868(3) 0.3350(4) 0.0410(11) Uani d 1 . .
    C C52 0.1112(4) 0.4028(4) 0.2926(4) 0.0412(13) Uani d 1 . .
    H H52 0.0749 0.4170 0.3383 0.049 Uiso calc 1 . .
    C C53 0.0612(4) 0.4000(4) 0.1855(4) 0.0378(12) Uani d 1 . .
    H H53 -0.0076 0.4115 0.1590 0.045 Uiso calc 1 . .
    C C54 0.1135(4) 0.3797(3) 0.1161(4) 0.0288(10) Uani d 1 . .
    C C55 0.2127(4) 0.3621(4) 0.1615(4) 0.0369(12) Uani d 1 . .
    H H55 0.2511 0.3461 0.1185 0.044 Uiso calc 1 . .
    C C56 0.2566(4) 0.3675(4) 0.2692(4) 0.0385(12) Uani d 1 . .
    H H56 0.3254 0.3569 0.2981 0.046 Uiso calc 1 . .
    C C57 0.0598(4) 0.3758(3) 0.0033(4) 0.0337(11) Uani d 1 . .
    H H57 -0.0094 0.3849 -0.0191 0.040 Uiso calc 1 . .
    N N61 -0.0448(4) 0.3520(3) -0.4024(4) 0.0395(10) Uani d 1 . .
    C C62 0.0518(4) 0.3542(4) -0.3613(4) 0.0377(12) Uani d 1 . .
    H H62 0.0891 0.3545 -0.4077 0.045 Uiso calc 1 . .
    C C63 0.1018(4) 0.3561(4) -0.2540(4) 0.0374(12) Uani d 1 . .
    H H63 0.1716 0.3577 -0.2285 0.045 Uiso calc 1 . .
    C C64 0.0498(4) 0.3558(4) -0.1838(4) 0.0329(11) Uani d 1 . .
    C C65 -0.0532(4) 0.3533(4) -0.2285(4) 0.0375(12) Uani d 1 . .
    H H65 -0.0935 0.3532 -0.1852 0.045 Uiso calc 1 . .
    C C66 -0.0940(5) 0.3511(4) -0.3350(4) 0.0451(14) Uani d 1 . .
    H H66 -0.1636 0.3487 -0.3636 0.054 Uiso calc 1 . .
    C C67 0.1014(4) 0.3601(4) -0.0712(4) 0.0349(11) Uani d 1 . .
    H H67 0.1707 0.3510 -0.0481 0.042 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
    C11 C24 . 1.375(7) ?
    C11 C16 . 1.428(7) ?
    C11 C12 . 1.454(7) ?
    C12 C13 . 1.358(7) ?
    C12 C31 . 1.437(7) ?
    C13 C14 . 1.427(7) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.357(7) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.420(7) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.396(7) ?
    C17 C18 . 1.384(7) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.425(7) ?
    C18 C23 . 1.433(6) ?
    C19 C20 . 1.360(7) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.408(8) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.393(7) ?
    C21 H21 . 0.9500 ?
    C22 C41 . 1.432(7) ?
    C22 C23 . 1.436(7) ?
    C23 C24 . 1.394(6) ?
    C24 H24 . 0.9500 ?
    C31 C32 . 1.208(7) ?
    C32 I1 . 2.018(6) ?
    I1 N51 . 2.775(5) ?
    C41 C42 . 1.211(7) ?
    C42 I2 . 2.013(5) ?
    I2 N61 . 13.594(5) ?
    N51 C52 . 1.326(7) ?
    N51 C56 . 1.338(7) ?
    C52 C53 . 1.384(7) ?
    C52 H52 . 0.9500 ?
    C53 C54 . 1.410(7) ?
    C53 H53 . 0.9500 ?
    C54 C55 . 1.378(7) ?
    C54 C57 . 1.459(7) ?
    C55 C56 . 1.379(7) ?
    C55 H55 . 0.9500 ?
    C56 H56 . 0.9500 ?
    C57 C67 . 1.348(8) ?
    C57 H57 . 0.9500 ?
    N61 C62 . 1.318(7) ?
    N61 C66 . 1.324(7) ?
    C62 C63 . 1.386(7) ?
    C62 H62 . 0.9500 ?
    C63 C64 . 1.390(7) ?
    C63 H63 . 0.9500 ?
    C64 C65 . 1.407(8) ?
    C64 C67 . 1.452(7) ?
    C65 C66 . 1.359(8) ?
    C65 H65 . 0.9500 ?
    C66 H66 . 0.9500 ?
    C67 H67 . 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
    C24 C11 C16 . . 120.0(4) ?
    C24 C11 C12 . . 121.5(4) ?
    C16 C11 C12 . . 118.5(5) ?
    C13 C12 C31 . . 121.3(5) ?
    C13 C12 C11 . . 120.1(5) ?
    C31 C12 C11 . . 118.7(4) ?
    C12 C13 C14 . . 120.5(5) ?
    C12 C13 H13 . . 119.7 ?
    C14 C13 H13 . . 119.7 ?
    C15 C14 C13 . . 120.8(5) ?
    C15 C14 H14 . . 119.6 ?
    C13 C14 H14 . . 119.6 ?
    C14 C15 C16 . . 120.9(5) ?
    C14 C15 H15 . . 119.5 ?
    C16 C15 H15 . . 119.5 ?
    C17 C16 C15 . . 122.2(5) ?
    C17 C16 C11 . . 118.8(5) ?
    C15 C16 C11 . . 119.0(5) ?
    C18 C17 C16 . . 121.8(5) ?
    C18 C17 H17 . . 119.1 ?
    C16 C17 H17 . . 119.1 ?
    C17 C18 C19 . . 121.8(5) ?
    C17 C18 C23 . . 118.8(4) ?
    C19 C18 C23 . . 119.4(5) ?
    C20 C19 C18 . . 119.7(5) ?
    C20 C19 H19 . . 120.1 ?
    C18 C19 H19 . . 120.1 ?
    C19 C20 C21 . . 122.8(5) ?
    C19 C20 H20 . . 118.6 ?
    C21 C20 H20 . . 118.6 ?
    C22 C21 C20 . . 119.0(5) ?
    C22 C21 H21 . . 120.5 ?
    C20 C21 H21 . . 120.5 ?
    C21 C22 C41 . . 120.9(5) ?
    C21 C22 C23 . . 120.4(5) ?
    C41 C22 C23 . . 118.6(4) ?
    C24 C23 C18 . . 119.5(4) ?
    C24 C23 C22 . . 121.8(4) ?
    C18 C23 C22 . . 118.7(4) ?
    C11 C24 C23 . . 121.2(4) ?
    C11 C24 H24 . . 119.4 ?
    C23 C24 H24 . . 119.4 ?
    C32 C31 C12 . . 177.6(6) ?
    C31 C32 I1 . . 178.9(5) ?
    C32 I1 N51 . . 176.07(18) ?
    C42 C41 C22 . . 175.8(6) ?
    C41 C42 I2 . . 178.3(5) ?
    C42 I2 N61 . . 155.36(15) ?
    C52 N51 C56 . . 117.2(5) ?
    C52 N51 I1 . . 124.8(4) ?
    C56 N51 I1 . . 117.6(4) ?
    N51 C52 C53 . . 123.5(5) ?
    N51 C52 H52 . . 118.3 ?
    C53 C52 H52 . . 118.3 ?
    C52 C53 C54 . . 119.3(5) ?
    C52 C53 H53 . . 120.3 ?
    C54 C53 H53 . . 120.3 ?
    C55 C54 C53 . . 116.4(5) ?
    C55 C54 C57 . . 124.7(5) ?
    C53 C54 C57 . . 118.9(5) ?
    C54 C55 C56 . . 120.3(5) ?
    C54 C55 H55 . . 119.9 ?
    C56 C55 H55 . . 119.9 ?
    N51 C56 C55 . . 123.3(5) ?
    N51 C56 H56 . . 118.3 ?
    C55 C56 H56 . . 118.3 ?
    C67 C57 C54 . . 124.7(5) ?
    C67 C57 H57 . . 117.7 ?
    C54 C57 H57 . . 117.7 ?
    C62 N61 C66 . . 116.4(5) ?
    C62 N61 I2 . . 76.1(3) ?
    C66 N61 I2 . . 43.1(3) ?
    N61 C62 C63 . . 123.3(5) ?
    N61 C62 H62 . . 118.3 ?
    C63 C62 H62 . . 118.3 ?
    C62 C63 C64 . . 120.0(5) ?
    C62 C63 H63 . . 120.0 ?
    C64 C63 H63 . . 120.0 ?
    C63 C64 C65 . . 116.1(5) ?
    C63 C64 C67 . . 120.4(5) ?
    C65 C64 C67 . . 123.5(5) ?
    C66 C65 C64 . . 118.5(5) ?
    C66 C65 H65 . . 120.7 ?
    C64 C65 H65 . . 120.7 ?
    N61 C66 C65 . . 125.6(6) ?
    N61 C66 H66 . . 117.2 ?
    C65 C66 H66 . . 117.2 ?
    C57 C67 C64 . . 125.7(5) ?
    C57 C67 H67 . . 117.1 ?
    C64 C67 H67 . . 117.1 ?
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
    C24 C11 C12 C13 . . . . -179.1(5) ?
    C16 C11 C12 C13 . . . . 2.4(7) ?
    C24 C11 C12 C31 . . . . 1.0(7) ?
    C16 C11 C12 C31 . . . . -177.6(5) ?
    C31 C12 C13 C14 . . . . 178.7(5) ?
    C11 C12 C13 C14 . . . . -1.3(8) ?
    C12 C13 C14 C15 . . . . -0.1(8) ?
    C13 C14 C15 C16 . . . . 0.3(8) ?
    C14 C15 C16 C17 . . . . -178.8(5) ?
    C14 C15 C16 C11 . . . . 0.9(8) ?
    C24 C11 C16 C17 . . . . -1.1(7) ?
    C12 C11 C16 C17 . . . . 177.5(5) ?
    C24 C11 C16 C15 . . . . 179.3(5) ?
    C12 C11 C16 C15 . . . . -2.2(7) ?
    C15 C16 C17 C18 . . . . -178.3(5) ?
    C11 C16 C17 C18 . . . . 2.0(8) ?
    C16 C17 C18 C19 . . . . 179.3(5) ?
    C16 C17 C18 C23 . . . . -1.1(7) ?
    C17 C18 C19 C20 . . . . -177.9(5) ?
    C23 C18 C19 C20 . . . . 2.4(7) ?
    C18 C19 C20 C21 . . . . -2.1(8) ?
    C19 C20 C21 C22 . . . . 0.6(8) ?
    C20 C21 C22 C41 . . . . -177.9(5) ?
    C20 C21 C22 C23 . . . . 0.5(8) ?
    C17 C18 C23 C24 . . . . -0.8(7) ?
    C19 C18 C23 C24 . . . . 178.9(5) ?
    C17 C18 C23 C22 . . . . 179.1(4) ?
    C19 C18 C23 C22 . . . . -1.3(7) ?
    C21 C22 C23 C24 . . . . 179.7(5) ?
    C41 C22 C23 C24 . . . . -1.9(7) ?
    C21 C22 C23 C18 . . . . -0.2(7) ?
    C41 C22 C23 C18 . . . . 178.3(4) ?
    C16 C11 C24 C23 . . . . -0.8(7) ?
    C12 C11 C24 C23 . . . . -179.3(4) ?
    C18 C23 C24 C11 . . . . 1.7(7) ?
    C22 C23 C24 C11 . . . . -178.1(5) ?
    C56 N51 C52 C53 . . . . 0.3(8) ?
    I1 N51 C52 C53 . . . . -172.0(4) ?
    N51 C52 C53 C54 . . . . -0.4(9) ?
    C52 C53 C54 C55 . . . . 1.2(7) ?
    C52 C53 C54 C57 . . . . 179.3(5) ?
    C53 C54 C55 C56 . . . . -1.9(7) ?
    C57 C54 C55 C56 . . . . -179.9(5) ?
    C52 N51 C56 C55 . . . . -1.1(8) ?
    I1 N51 C56 C55 . . . . 171.8(4) ?
    C54 C55 C56 N51 . . . . 1.9(8) ?
    C55 C54 C57 C67 . . . . -4.1(8) ?
    C53 C54 C57 C67 . . . . 177.9(5) ?
    C66 N61 C62 C63 . . . . -0.4(8) ?
    I2 N61 C62 C63 . . . . 15.3(4) ?
    N61 C62 C63 C64 . . . . 0.0(8) ?
    C62 C63 C64 C65 . . . . 0.1(7) ?
    C62 C63 C64 C67 . . . . -178.6(5) ?
    C63 C64 C65 C66 . . . . 0.2(7) ?
    C67 C64 C65 C66 . . . . 178.9(5) ?
    C62 N61 C66 C65 . . . . 0.7(9) ?
    I2 N61 C66 C65 . . . . -21.8(4) ?
    C64 C65 C66 N61 . . . . -0.7(9) ?
    C54 C57 C67 C64 . . . . 180.0(4) ?
    C63 C64 C67 C57 . . . . 168.9(5) ?
    C65 C64 C67 C57 . . . . -9.7(8) ?
_shelxl_version_number     .2013
