##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-06-07
_journal_date_accepted     2005-06-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      7
_journal_page_first     m1368
_journal_page_last     m1369
_journal_paper_category     EM
_publ_contact_author_name     'Dr. Andrzej Kochel'
_publ_contact_author_address
;Faculty of Chemistry
 University of Wrocław
 F-Jolit Curie St.14
 50-383 Wro\/aw
;
_publ_contact_author_email     andrzej@wchuwr.chem.uni.wroc.pl
_publ_contact_author_phone     '+49713757240'
_publ_section_title
;
Bis[4,4'-dimethyl-2,2'-bipyridinium(+)] tetraoxorhenium triiodide
;
loop_
    _publ_author_name
    _publ_author_address
    'Andrzej Kochel'
;
Faculty of Chemistry
Univesity of Wrocław
F. Joliot Curie St. 14
50-383 Wroclaw
Poland
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis[4,4'-dimethyl-2,2'-bipyridinium(+)] tetraoxorhenium triiodide
;
_chemical_formula_moiety     '2C12 H13 N2 +, O4 Re -, I3 -'
_chemical_formula_sum     'C24 H26 I3 N4 O4 Re'
_chemical_formula_iupac     '(C12 H13 N2)2 [Re O4] I3'
_chemical_formula_weight     1001.40
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.667(2)
_cell_length_b     12.096(2)
_cell_length_c     14.185(3)
_cell_angle_alpha     66.41(3)
_cell_angle_beta     85.10(3)
_cell_angle_gamma     74.07(3)
_cell_volume     1461.1(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5240
_cell_measurement_theta_min     2.96
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     2.276
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     928
_exptl_absorpt_coefficient_mu     7.363
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_correction_T_min     0.378
_exptl_absorpt_correction_T_max     0.595
_diffrn_ambient_temperature     100(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     KM-4/CCD
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19623
_diffrn_reflns_av_R_equivalents     0.0492
_diffrn_reflns_av_sigmaI/netI     0.0381
_diffrn_reflns_theta_min     2.96
_diffrn_reflns_theta_max     28.48
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.923
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     6808
_reflns_number_gt     5964
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0335
_refine_ls_R_factor_gt     0.0261
_refine_ls_wR_factor_gt     0.0572
_refine_ls_wR_factor_ref     0.0590
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     6808
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0325P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap (N-H) and geom (C-H)'
_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     1.606
_refine_diff_density_min     -1.092
_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'
    'Re' 'Re' -1.0185 7.2310
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KM4CCD (Oxford Diffraction, 2004)'
_computing_cell_refinement     'KM4CCD'
_computing_data_reduction     'KM4CCD'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     SHELXL97
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Re1 0.761289(15) 0.191131(13) 0.612676(11) 0.01351(5) Uani d . 1 . . Re
    O1 0.6457(3) 0.1071(3) 0.6886(2) 0.0211(6) Uani d . 1 . . O
    O2 0.6655(3) 0.3423(2) 0.5396(2) 0.0204(6) Uani d . 1 . . O
    O3 0.8860(3) 0.1931(3) 0.6933(2) 0.0196(6) Uani d . 1 . . O
    O4 0.8488(3) 0.1189(3) 0.5333(2) 0.0227(6) Uani d . 1 . . O
    I1 0.30184(3) 0.97182(3) 0.04451(2) 0.02782(7) Uani d . 1 . . I
    I2 0.0000 1.0000 0.0000 0.02189(8) Uani d S 1 . . I
    I3 0.79056(3) 0.47696(3) 0.06214(2) 0.03004(7) Uani d . 1 . . I
    I4 0.5000 0.5000 0.0000 0.02175(8) Uani d S 1 . . I
    H1A 0.483(5) 0.086(5) 0.655(4) 0.043(14) Uiso d . 1 . . H
    H2A 0.057(5) 0.276(5) 0.644(4) 0.046(16) Uiso d . 1 . . H
    N1 0.4706(3) 0.1846(3) 0.4828(2) 0.0148(6) Uani d . 1 . . N
    N2 0.4019(3) 0.0476(3) 0.6684(2) 0.0123(6) Uani d . 1 . . N
    C1 0.3772(4) -0.0150(3) 0.7679(3) 0.0155(7) Uani d . 1 . . C
    H1 0.4367 -0.0203 0.8203 0.019 Uiso calc R 1 . . H
    C2 0.2657(4) -0.0715(3) 0.7939(3) 0.0151(7) Uani d . 1 . . C
    H2 0.2508 -0.1192 0.8639 0.018 Uiso calc R 1 . . H
    C3 0.1748(4) -0.0580(3) 0.7165(3) 0.0143(7) Uani d . 1 . . C
    C4 0.2032(4) 0.0084(3) 0.6135(3) 0.0149(7) Uani d . 1 . . C
    H4 0.1428 0.0179 0.5599 0.018 Uiso calc R 1 . . H
    C5 0.3193(4) 0.0603(3) 0.5900(3) 0.0114(7) Uani d . 1 . . C
    C6 0.3643(4) 0.1313(3) 0.4850(3) 0.0118(7) Uani d . 1 . . C
    C7 0.3011(4) 0.1397(3) 0.3971(3) 0.0152(7) Uani d . 1 . . C
    H7 0.2279 0.0988 0.4029 0.018 Uiso calc R 1 . . H
    C8 0.3462(4) 0.2089(3) 0.2999(3) 0.0151(7) Uani d . 1 . . C
    C9 0.4548(4) 0.2649(3) 0.2978(3) 0.0162(7) Uani d . 1 . . C
    H9 0.4887 0.3133 0.2338 0.019 Uiso calc R 1 . . H
    C10 0.5140(4) 0.2498(3) 0.3898(3) 0.0153(7) Uani d . 1 . . C
    H10 0.5892 0.2878 0.3863 0.018 Uiso calc R 1 . . H
    C11 0.2805(4) 0.2203(4) 0.2033(3) 0.0202(8) Uani d . 1 . . C
    H11A 0.1807 0.2714 0.1949 0.030 Uiso calc R 1 . . H
    H11B 0.2823 0.1369 0.2078 0.030 Uiso calc R 1 . . H
    H11C 0.3355 0.2600 0.1441 0.030 Uiso calc R 1 . . H
    C12 0.0506(4) -0.1167(4) 0.7428(3) 0.0212(8) Uani d . 1 . . C
    H12A 0.0064 -0.1071 0.6794 0.032 Uiso calc R 1 . . H
    H12B -0.0209 -0.0755 0.7798 0.032 Uiso calc R 1 . . H
    H12C 0.0855 -0.2058 0.7864 0.032 Uiso calc R 1 . . H
    N3 0.0317(3) 0.3342(3) 0.4812(2) 0.0141(6) Uani d . 1 . . N
    N4 0.1246(3) 0.2830(3) 0.6674(2) 0.0125(6) Uani d . 1 . . N
    C20 0.1622(4) 0.2446(3) 0.7668(3) 0.0154(7) Uani d . 1 . . C
    H20 0.1114 0.1948 0.8195 0.019 Uiso calc R 1 . . H
    C21 0.2745(4) 0.2780(3) 0.7917(3) 0.0143(7) Uani d . 1 . . C
    H21 0.3008 0.2521 0.8618 0.017 Uiso calc R 1 . . H
    C22 0.3497(4) 0.3497(3) 0.7142(3) 0.0124(7) Uani d . 1 . . C
    C23 0.3088(4) 0.3854(3) 0.6124(3) 0.0135(7) Uani d . 1 . . C
    H23 0.3610 0.4320 0.5585 0.016 Uiso calc R 1 . . H
    C24 0.1919(3) 0.3535(3) 0.5882(3) 0.0120(7) Uani d . 1 . . C
    C25 0.1361(4) 0.3877(3) 0.4836(3) 0.0125(7) Uani d . 1 . . C
    C26 0.1868(4) 0.4692(3) 0.3958(3) 0.0145(7) Uani d . 1 . . C
    H26 0.2593 0.5057 0.4017 0.017 Uiso calc R 1 . . H
    C27 0.1309(4) 0.4967(3) 0.2994(3) 0.0141(7) Uani d . 1 . . C
    C28 0.0233(4) 0.4408(3) 0.2967(3) 0.0171(8) Uani d . 1 . . C
    H28 -0.0184 0.4567 0.2328 0.021 Uiso calc R 1 . . H
    C29 -0.0225(4) 0.3619(3) 0.3881(3) 0.0172(8) Uani d . 1 . . C
    H29 -0.0963 0.3256 0.3844 0.021 Uiso calc R 1 . . H
    C30 0.1829(4) 0.5830(4) 0.2024(3) 0.0207(8) Uani d . 1 . . C
    H30A 0.1854 0.6591 0.2106 0.031 Uiso calc R 1 . . H
    H30B 0.1174 0.6050 0.1448 0.031 Uiso calc R 1 . . H
    H30C 0.2798 0.5412 0.1884 0.031 Uiso calc R 1 . . H
    C31 0.4720(4) 0.3881(4) 0.7401(3) 0.0197(8) Uani d . 1 . . C
    H31A 0.4389 0.4308 0.7871 0.030 Uiso calc R 1 . . H
    H31B 0.5055 0.4449 0.6769 0.030 Uiso calc R 1 . . H
    H31C 0.5511 0.3138 0.7732 0.030 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Re1 0.01382(7) 0.01468(8) 0.01384(8) -0.00674(5) -0.00023(5) -0.00535(6)
    O1 0.0215(14) 0.0256(14) 0.0159(14) -0.0138(12) -0.0035(11) -0.0021(12)
    O2 0.0218(14) 0.0155(13) 0.0216(14) -0.0055(11) -0.0035(11) -0.0038(12)
    O3 0.0173(13) 0.0281(15) 0.0183(14) -0.0127(11) 0.0023(11) -0.0099(12)
    O4 0.0232(14) 0.0244(14) 0.0262(15) -0.0088(12) 0.0034(12) -0.0146(13)
    I1 0.03121(15) 0.03595(16) 0.01561(13) -0.01209(12) -0.00124(11)
                                                                    -0.00693(12)
    I2 0.02687(19) 0.02420(18) 0.01404(17) -0.01041(15) 0.00604(14) -0.00561(15)
    I3 0.03017(15) 0.03368(16) 0.02406(14) -0.00186(12) -0.00975(12)
                                                                    -0.01133(13)
    I4 0.02850(19) 0.02214(18) 0.01107(16) -0.00466(15) -0.00027(14)
                                                                    -0.00409(14)
    N1 0.0141(15) 0.0130(15) 0.0163(16) -0.0043(12) -0.0008(12) -0.0041(13)
    N2 0.0102(14) 0.0132(14) 0.0140(15) -0.0012(12) -0.0010(12) -0.0069(13)
    C1 0.0141(17) 0.0189(18) 0.0134(18) -0.0007(15) -0.0016(14) -0.0083(15)
    C2 0.0138(17) 0.0138(17) 0.0162(18) -0.0038(14) 0.0022(14) -0.0046(15)
    C3 0.0129(17) 0.0149(17) 0.0175(18) -0.0037(14) 0.0014(14) -0.0091(15)
    C4 0.0124(17) 0.0166(18) 0.0157(18) -0.0026(14) 0.0000(14) -0.0069(15)
    C5 0.0092(16) 0.0104(16) 0.0143(17) 0.0001(13) 0.0010(13) -0.0066(14)
    C6 0.0104(16) 0.0119(16) 0.0125(17) 0.0003(13) 0.0002(13) -0.0062(14)
    C7 0.0131(17) 0.0119(17) 0.0193(19) -0.0013(14) -0.0003(15) -0.0059(15)
    C8 0.0167(18) 0.0142(17) 0.0105(17) -0.0013(14) 0.0011(14) -0.0030(15)
    C9 0.0169(18) 0.0134(17) 0.0133(18) -0.0024(14) 0.0013(14) -0.0014(15)
    C10 0.0104(16) 0.0172(18) 0.0179(19) -0.0053(14) 0.0008(14) -0.0054(15)
    C11 0.023(2) 0.021(2) 0.0146(19) -0.0033(16) -0.0026(16) -0.0068(16)
    C12 0.0207(19) 0.022(2) 0.020(2) -0.0109(16) 0.0027(16) -0.0041(17)
    N3 0.0095(14) 0.0184(15) 0.0158(15) -0.0018(12) -0.0021(12) -0.0090(13)
    N4 0.0072(14) 0.0123(14) 0.0171(16) -0.0015(12) 0.0000(12) -0.0054(13)
    C20 0.0162(18) 0.0124(17) 0.0138(18) -0.0027(14) 0.0015(14) -0.0022(15)
    C21 0.0144(17) 0.0130(17) 0.0135(18) -0.0003(14) -0.0040(14) -0.0044(15)
    C22 0.0099(16) 0.0134(16) 0.0153(17) -0.0009(13) -0.0019(13) -0.0082(15)
    C23 0.0094(16) 0.0130(17) 0.0168(18) -0.0024(13) 0.0002(14) -0.0048(15)
    C24 0.0084(16) 0.0103(16) 0.0162(18) 0.0008(13) -0.0014(14) -0.0058(14)
    C25 0.0090(16) 0.0125(16) 0.0172(18) 0.0007(13) -0.0011(14) -0.0089(15)
    C26 0.0120(17) 0.0130(17) 0.0179(19) -0.0011(14) 0.0000(14) -0.0067(15)
    C27 0.0126(17) 0.0144(17) 0.0149(18) 0.0014(14) 0.0001(14) -0.0083(15)
    C28 0.0156(18) 0.0191(19) 0.0186(19) -0.0004(15) -0.0033(15) -0.0114(16)
    C29 0.0124(17) 0.0215(19) 0.021(2) -0.0046(15) -0.0036(15) -0.0112(17)
    C30 0.0196(19) 0.027(2) 0.0146(19) -0.0042(16) 0.0003(15) -0.0081(17)
    C31 0.0169(19) 0.025(2) 0.022(2) -0.0086(16) -0.0018(16) -0.0114(17)
_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
    Re1 O4 . 1.723(3) y
    Re1 O1 . 1.727(3) y
    Re1 O2 . 1.730(3) y
    Re1 O3 . 1.741(3) y
    I1 I2 . 2.9369(8) y
    I2 I1 2_575 2.9369(8) ?
    I3 I4 . 2.9224(8) y
    I4 I3 2_665 2.9224(8) ?
    N1 C10 . 1.339(5) ?
    N1 C6 . 1.347(4) ?
    N2 C1 . 1.345(5) ?
    N2 C5 . 1.359(4) ?
    N2 H1A . 0.99(5) ?
    C1 C2 . 1.378(5) ?
    C1 H1 . 0.9500 ?
    C2 C3 . 1.396(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.403(5) ?
    C3 C12 . 1.504(5) ?
    C4 C5 . 1.386(5) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.488(5) ?
    C6 C7 . 1.390(5) ?
    C7 C8 . 1.402(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.389(5) ?
    C8 C11 . 1.501(5) ?
    C9 C10 . 1.395(5) ?
    C9 H9 . 0.9500 ?
    C10 H10 . 0.9500 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    N3 C29 . 1.341(5) ?
    N3 C25 . 1.349(4) ?
    N4 C20 . 1.344(5) ?
    N4 C24 . 1.350(4) ?
    N4 H2A . 0.80(5) ?
    C20 C21 . 1.373(5) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.391(5) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.391(5) ?
    C22 C31 . 1.504(5) ?
    C23 C24 . 1.398(5) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.480(5) ?
    C25 C26 . 1.393(5) ?
    C26 C27 . 1.391(5) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.398(5) ?
    C27 C30 . 1.502(5) ?
    C28 C29 . 1.389(5) ?
    C28 H28 . 0.9500 ?
    C29 H29 . 0.9500 ?
    C30 H30A . 0.9800 ?
    C30 H30B . 0.9800 ?
    C30 H30C . 0.9800 ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
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
    O4 Re1 O1 . . 109.06(13) ?
    O4 Re1 O2 . . 109.89(14) ?
    O1 Re1 O2 . . 109.96(13) ?
    O4 Re1 O3 . . 109.79(12) ?
    O1 Re1 O3 . . 108.12(12) ?
    O2 Re1 O3 . . 110.00(13) ?
    I1 I2 I1 2_575 . 180.0 ?
    I3 I4 I3 2_665 . 180.0 ?
    C10 N1 C6 . . 116.7(3) ?
    C1 N2 C5 . . 122.8(3) ?
    C1 N2 H1A . . 116(3) ?
    C5 N2 H1A . . 121(3) ?
    N2 C1 C2 . . 120.1(3) ?
    N2 C1 H1 . . 120.0 ?
    C2 C1 H1 . . 120.0 ?
    C1 C2 C3 . . 119.4(3) ?
    C1 C2 H2 . . 120.3 ?
    C3 C2 H2 . . 120.3 ?
    C2 C3 C4 . . 119.0(3) ?
    C2 C3 C12 . . 120.5(3) ?
    C4 C3 C12 . . 120.5(3) ?
    C5 C4 C3 . . 120.1(3) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    N2 C5 C4 . . 118.6(3) ?
    N2 C5 C6 . . 115.1(3) ?
    C4 C5 C6 . . 126.3(3) ?
    N1 C6 C7 . . 123.5(3) ?
    N1 C6 C5 . . 114.8(3) ?
    C7 C6 C5 . . 121.7(3) ?
    C6 C7 C8 . . 119.6(3) ?
    C6 C7 H7 . . 120.2 ?
    C8 C7 H7 . . 120.2 ?
    C9 C8 C7 . . 116.9(3) ?
    C9 C8 C11 . . 122.0(3) ?
    C7 C8 C11 . . 121.2(3) ?
    C8 C9 C10 . . 119.8(3) ?
    C8 C9 H9 . . 120.1 ?
    C10 C9 H9 . . 120.1 ?
    N1 C10 C9 . . 123.6(3) ?
    N1 C10 H10 . . 118.2 ?
    C9 C10 H10 . . 118.2 ?
    C8 C11 H11A . . 109.5 ?
    C8 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C8 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C3 C12 H12A . . 109.5 ?
    C3 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C3 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C29 N3 C25 . . 116.6(3) ?
    C20 N4 C24 . . 123.7(3) ?
    C20 N4 H2A . . 128(4) ?
    C24 N4 H2A . . 108(4) ?
    N4 C20 C21 . . 119.5(3) ?
    N4 C20 H20 . . 120.2 ?
    C21 C20 H20 . . 120.2 ?
    C20 C21 C22 . . 120.0(3) ?
    C20 C21 H21 . . 120.0 ?
    C22 C21 H21 . . 120.0 ?
    C23 C22 C21 . . 118.5(3) ?
    C23 C22 C31 . . 120.8(3) ?
    C21 C22 C31 . . 120.7(3) ?
    C22 C23 C24 . . 120.8(3) ?
    C22 C23 H23 . . 119.6 ?
    C24 C23 H23 . . 119.6 ?
    N4 C24 C23 . . 117.3(3) ?
    N4 C24 C25 . . 116.6(3) ?
    C23 C24 C25 . . 126.1(3) ?
    N3 C25 C26 . . 123.4(3) ?
    N3 C25 C24 . . 114.1(3) ?
    C26 C25 C24 . . 122.4(3) ?
    C27 C26 C25 . . 119.7(3) ?
    C27 C26 H26 . . 120.2 ?
    C25 C26 H26 . . 120.2 ?
    C26 C27 C28 . . 117.0(3) ?
    C26 C27 C30 . . 121.7(3) ?
    C28 C27 C30 . . 121.3(3) ?
    C29 C28 C27 . . 119.7(3) ?
    C29 C28 H28 . . 120.2 ?
    C27 C28 H28 . . 120.2 ?
    N3 C29 C28 . . 123.7(3) ?
    N3 C29 H29 . . 118.2 ?
    C28 C29 H29 . . 118.2 ?
    C27 C30 H30A . . 109.5 ?
    C27 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C27 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C22 C31 H31A . . 109.5 ?
    C22 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C22 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
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
    C5 N2 C1 C2 . . . . 1.1(5) ?
    N2 C1 C2 C3 . . . . -3.0(5) ?
    C1 C2 C3 C4 . . . . 2.7(5) ?
    C1 C2 C3 C12 . . . . -178.9(3) ?
    C2 C3 C4 C5 . . . . -0.5(5) ?
    C12 C3 C4 C5 . . . . -178.9(3) ?
    C1 N2 C5 C4 . . . . 1.2(5) ?
    C1 N2 C5 C6 . . . . -179.2(3) ?
    C3 C4 C5 N2 . . . . -1.4(5) ?
    C3 C4 C5 C6 . . . . 179.0(3) ?
    C10 N1 C6 C7 . . . . 0.8(5) ?
    C10 N1 C6 C5 . . . . -179.8(3) ?
    N2 C5 C6 N1 . . . . -7.0(4) ?
    C4 C5 C6 N1 . . . . 172.6(3) ?
    N2 C5 C6 C7 . . . . 172.4(3) ?
    C4 C5 C6 C7 . . . . -8.0(5) ?
    N1 C6 C7 C8 . . . . -1.4(5) ?
    C5 C6 C7 C8 . . . . 179.3(3) ?
    C6 C7 C8 C9 . . . . 0.7(5) ?
    C6 C7 C8 C11 . . . . -179.9(3) ?
    C7 C8 C9 C10 . . . . 0.4(5) ?
    C11 C8 C9 C10 . . . . -179.0(3) ?
    C6 N1 C10 C9 . . . . 0.4(5) ?
    C8 C9 C10 N1 . . . . -1.0(5) ?
    C24 N4 C20 C21 . . . . 0.4(5) ?
    N4 C20 C21 C22 . . . . -0.8(5) ?
    C20 C21 C22 C23 . . . . -0.3(5) ?
    C20 C21 C22 C31 . . . . 179.3(3) ?
    C21 C22 C23 C24 . . . . 2.0(5) ?
    C31 C22 C23 C24 . . . . -177.7(3) ?
    C20 N4 C24 C23 . . . . 1.3(5) ?
    C20 N4 C24 C25 . . . . -179.8(3) ?
    C22 C23 C24 N4 . . . . -2.5(5) ?
    C22 C23 C24 C25 . . . . 178.7(3) ?
    C29 N3 C25 C26 . . . . 0.7(5) ?
    C29 N3 C25 C24 . . . . -179.8(3) ?
    N4 C24 C25 N3 . . . . -5.4(4) ?
    C23 C24 C25 N3 . . . . 173.4(3) ?
    N4 C24 C25 C26 . . . . 174.1(3) ?
    C23 C24 C25 C26 . . . . -7.1(5) ?
    N3 C25 C26 C27 . . . . -1.3(5) ?
    C24 C25 C26 C27 . . . . 179.3(3) ?
    C25 C26 C27 C28 . . . . 0.9(5) ?
    C25 C26 C27 C30 . . . . -179.5(3) ?
    C26 C27 C28 C29 . . . . -0.1(5) ?
    C30 C27 C28 C29 . . . . -179.7(3) ?
    C25 N3 C29 C28 . . . . 0.2(5) ?
    C27 C28 C29 N3 . . . . -0.5(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
    _geom_hbond_publ_flag
    N2 H1A O1 . 0.99(5) 1.79(5) 2.714(4) 154(5) yes
    N4 H2A O3 1_455 0.80(5) 2.09(5) 2.748(4) 140(5) yes
    C4 H4 O4 2_656 0.95 2.48 3.183(5) 130 yes
    C23 H23 O2 2_666 0.95 2.46 3.199(5) 133 yes
    C26 H26 O2 2_666 0.95 2.58 3.429(5) 148 yes
    C30 H30A O3 2_666 0.98 2.57 3.466(6) 151 yes
    C20 H20 I2 1_546 0.95 3.05 3.998(4) 169 yes
