#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:15:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178943 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/72/4117258.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4117258
loop_
_publ_author_name
'Kalyan V. Vasudevan'
'Michael Findlater'
'Ignacio Vargas-Baca'
'Alan H. Cowley'
_publ_contact_author_address
;
   Department of Chemistry and Biochemistry
   University of Texas-Austin
   1 University Station, A5300
   Austin, TX 78701
   USA
;
_publ_contact_author_email       cowley@mail.utexas.edu
_publ_contact_author_fax         512-471-6822
_publ_contact_author_name
;
Alan H. Cowley
;
_publ_contact_author_phone       512-471-7710
_publ_section_title
;
 Tetrakis(imino)pyracene Complexes Exhibiting Multielectron Redox
 Processes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              176
_journal_page_last               178
_journal_paper_doi               10.1021/ja2102828
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C62 H72 N4 B2 I2, (I5), 3(C H2 Cl2)'
_chemical_formula_sum            'C65 H78 B2 Cl6 I7 N4'
_chemical_formula_weight         2037.93
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.255(5)
_cell_angle_beta                 95.940(5)
_cell_angle_gamma                109.231(5)
_cell_formula_units_Z            2
_cell_length_a                   12.625(5)
_cell_length_b                   14.448(5)
_cell_length_c                   23.312(5)
_cell_measurement_temperature    153(2)
_cell_volume                     3890(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24731
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    2.826
_exptl_absorpt_correction_T_max  0.634
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'DENZO and Scalepack (Otwinoski and Minor, 1997)'
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             1958
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.427
_refine_diff_density_min         -1.497
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         17495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0995P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                11927
_reflns_number_total             17495
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2102828_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4117258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8918(4) 0.3237(4) 0.9063(2) 0.0237(10) Uani 1 1 d .
C2 C 0.9815(4) 0.4205(4) 0.9239(2) 0.0269(11) Uani 1 1 d .
C3 C 0.9666(4) 0.4557(4) 0.9830(2) 0.0244(10) Uani 1 1 d .
C4 C 0.8759(4) 0.3881(4) 1.0030(2) 0.0247(10) Uani 1 1 d .
C5 C 0.8300(4) 0.3036(4) 0.9519(2) 0.0252(11) Uani 1 1 d .
C6 C 0.8573(4) 0.4199(4) 1.0599(2) 0.0253(11) Uani 1 1 d .
H6 H 0.7969 0.3787 1.0739 0.030 Uiso 1 1 calc R
C7 C 0.9294(4) 0.5148(4) 1.0971(2) 0.0274(11) Uani 1 1 d .
H7 H 0.9171 0.5335 1.1354 0.033 Uiso 1 1 calc R
C8 C 0.9033(4) 0.2397(4) 0.8072(2) 0.0264(11) Uani 1 1 d .
C9 C 1.0035(5) 0.2212(4) 0.8120(2) 0.0318(12) Uani 1 1 d .
C10 C 1.0583(5) 0.2229(5) 0.7630(3) 0.0397(14) Uani 1 1 d .
H10 H 1.1251 0.2085 0.7644 0.048 Uiso 1 1 calc R
C11 C 1.0157(6) 0.2452(5) 0.7129(3) 0.0439(15) Uani 1 1 d .
H11 H 1.0545 0.2476 0.6810 0.053 Uiso 1 1 calc R
C12 C 0.9175(5) 0.2638(4) 0.7095(2) 0.0386(14) Uani 1 1 d .
H12 H 0.8900 0.2784 0.6750 0.046 Uiso 1 1 calc R
C13 C 0.8558(5) 0.2620(4) 0.7556(2) 0.0324(12) Uani 1 1 d .
C14 C 1.0501(5) 0.1928(5) 0.8665(3) 0.0402(14) Uani 1 1 d .
H14 H 1.0183 0.2180 0.8999 0.048 Uiso 1 1 calc R
C15 C 1.0100(7) 0.0794(6) 0.8566(3) 0.0613(19) Uani 1 1 d .
H15A H 0.9286 0.0526 0.8529 0.092 Uiso 1 1 calc R
H15B H 1.0442 0.0613 0.8895 0.092 Uiso 1 1 calc R
H15C H 1.0318 0.0522 0.8209 0.092 Uiso 1 1 calc R
C16 C 1.1810(6) 0.2386(7) 0.8832(3) 0.066(2) Uani 1 1 d .
H16A H 1.2043 0.2288 0.9215 0.099 Uiso 1 1 calc R
H16B H 1.2061 0.3093 0.8842 0.099 Uiso 1 1 calc R
H16C H 1.2141 0.2062 0.8544 0.099 Uiso 1 1 calc R
C17 C 0.7468(5) 0.2853(4) 0.7522(2) 0.0367(13) Uani 1 1 d .
H17 H 0.7153 0.2734 0.7881 0.044 Uiso 1 1 calc R
C18 C 0.7706(7) 0.3940(6) 0.7510(5) 0.078(3) Uani 1 1 d .
H18A H 0.8172 0.4361 0.7877 0.118 Uiso 1 1 calc R
H18B H 0.7000 0.4057 0.7458 0.118 Uiso 1 1 calc R
H18C H 0.8097 0.4097 0.7189 0.118 Uiso 1 1 calc R
C19 C 0.6581(6) 0.2185(7) 0.6996(3) 0.064(2) Uani 1 1 d .
H19A H 0.6888 0.2254 0.6639 0.096 Uiso 1 1 calc R
H19B H 0.5923 0.2379 0.6984 0.096 Uiso 1 1 calc R
H19C H 0.6368 0.1498 0.7029 0.096 Uiso 1 1 calc R
C20 C 0.6812(4) 0.1671(4) 0.9781(2) 0.0237(10) Uani 1 1 d .
C21 C 0.7116(4) 0.0952(4) 1.0012(2) 0.0285(11) Uani 1 1 d .
C22 C 0.6559(5) 0.0609(4) 1.0463(2) 0.0337(13) Uani 1 1 d .
H22 H 0.6747 0.0137 1.0634 0.040 Uiso 1 1 calc R
C23 C 0.5740(5) 0.0956(5) 1.0659(2) 0.0401(15) Uani 1 1 d .
H23 H 0.5376 0.0717 1.0958 0.048 Uiso 1 1 calc R
C24 C 0.5457(5) 0.1660(5) 1.0409(2) 0.0400(15) Uani 1 1 d .
H24 H 0.4903 0.1893 1.0546 0.048 Uiso 1 1 calc R
C25 C 0.5979(4) 0.2026(4) 0.9960(2) 0.0308(12) Uani 1 1 d .
C26 C 0.8078(5) 0.0608(4) 0.9828(3) 0.0360(13) Uani 1 1 d .
H26 H 0.8264 0.0841 0.9469 0.043 Uiso 1 1 calc R
C27 C 0.7744(6) -0.0531(5) 0.9681(4) 0.063(2) Uani 1 1 d .
H27A H 0.7518 -0.0788 1.0019 0.094 Uiso 1 1 calc R
H27B H 0.8382 -0.0703 0.9577 0.094 Uiso 1 1 calc R
H27C H 0.7120 -0.0820 0.9354 0.094 Uiso 1 1 calc R
C28 C 0.9164(6) 0.1082(7) 1.0302(4) 0.073(2) Uani 1 1 d .
H28A H 0.9408 0.1801 1.0372 0.109 Uiso 1 1 calc R
H28B H 0.9754 0.0864 1.0167 0.109 Uiso 1 1 calc R
H28C H 0.9007 0.0875 1.0663 0.109 Uiso 1 1 calc R
C29 C 0.5634(5) 0.2780(5) 0.9665(3) 0.0390(13) Uani 1 1 d .
H29 H 0.6315 0.3227 0.9555 0.047 Uiso 1 1 calc R
C30 C 0.5142(8) 0.3428(7) 1.0062(4) 0.073(2) Uani 1 1 d .
H30A H 0.4489 0.3003 1.0187 0.110 Uiso 1 1 calc R
H30B H 0.4919 0.3861 0.9846 0.110 Uiso 1 1 calc R
H30C H 0.5707 0.3829 1.0402 0.110 Uiso 1 1 calc R
C31 C 0.4765(7) 0.2198(6) 0.9094(3) 0.065(2) Uani 1 1 d .
H31A H 0.4117 0.1713 0.9188 0.097 Uiso 1 1 calc R
H31B H 0.5113 0.1859 0.8823 0.097 Uiso 1 1 calc R
H31C H 0.4523 0.2661 0.8915 0.097 Uiso 1 1 calc R
C32 C 0.5962(4) 0.6785(4) 0.5931(2) 0.0258(11) Uani 1 1 d .
C33 C 0.5112(5) 0.5783(4) 0.5752(2) 0.0295(12) Uani 1 1 d .
C34 C 0.4240(4) 0.5115(4) 0.5951(2) 0.0294(12) Uani 1 1 d .
H34 H 0.4078 0.5305 0.6325 0.035 Uiso 1 1 calc R
C35 C 0.6419(4) 0.5866(4) 0.4413(2) 0.0282(11) Uani 1 1 d .
H35 H 0.7003 0.6304 0.4273 0.034 Uiso 1 1 calc R
C36 C 0.6187(4) 0.6162(4) 0.4970(2) 0.0272(11) Uani 1 1 d .
C37 C 0.5301(5) 0.5447(4) 0.5166(2) 0.0307(12) Uani 1 1 d .
C38 C 0.6588(4) 0.7000(4) 0.5479(2) 0.0257(11) Uani 1 1 d .
C39 C 0.5822(4) 0.7608(4) 0.6925(2) 0.0245(11) Uani 1 1 d .
C40 C 0.6353(5) 0.7444(4) 0.7439(2) 0.0328(12) Uani 1 1 d .
C41 C 0.5780(5) 0.7388(4) 0.7914(2) 0.0391(14) Uani 1 1 d .
H41 H 0.6111 0.7278 0.8259 0.047 Uiso 1 1 calc R
C42 C 0.4729(5) 0.7491(5) 0.7888(2) 0.0403(14) Uani 1 1 d .
H42 H 0.4349 0.7436 0.8208 0.048 Uiso 1 1 calc R
C43 C 0.4242(5) 0.7676(4) 0.7378(3) 0.0370(13) Uani 1 1 d .
H43 H 0.3537 0.7752 0.7363 0.044 Uiso 1 1 calc R
C44 C 0.4784(5) 0.7752(4) 0.6891(2) 0.0300(12) Uani 1 1 d .
C45 C 0.7501(6) 0.7299(5) 0.7476(3) 0.0441(15) Uani 1 1 d .
H45 H 0.7816 0.7478 0.7127 0.053 Uiso 1 1 calc R
C46 C 0.7382(7) 0.6233(6) 0.7452(4) 0.067(2) Uani 1 1 d .
H46A H 0.7027 0.6016 0.7774 0.100 Uiso 1 1 calc R
H46B H 0.8121 0.6176 0.7484 0.100 Uiso 1 1 calc R
H46C H 0.6920 0.5817 0.7083 0.100 Uiso 1 1 calc R
C47 C 0.8343(8) 0.8011(7) 0.8020(4) 0.082(3) Uani 1 1 d .
H47A H 0.8028 0.7902 0.8370 0.124 Uiso 1 1 calc R
H47B H 0.8485 0.8695 0.7991 0.124 Uiso 1 1 calc R
H47C H 0.9045 0.7885 0.8041 0.124 Uiso 1 1 calc R
C48 C 0.4252(5) 0.7994(5) 0.6349(3) 0.0376(13) Uani 1 1 d .
H48 H 0.4548 0.7739 0.6007 0.045 Uiso 1 1 calc R
C49 C 0.4615(8) 0.9131(6) 0.6435(4) 0.077(3) Uani 1 1 d .
H49A H 0.4470 0.9412 0.6811 0.116 Uiso 1 1 calc R
H49B H 0.4190 0.9287 0.6124 0.116 Uiso 1 1 calc R
H49C H 0.5413 0.9410 0.6424 0.116 Uiso 1 1 calc R
C50 C 0.2970(6) 0.7526(7) 0.6217(3) 0.064(2) Uani 1 1 d .
H50A H 0.2662 0.7778 0.6545 0.097 Uiso 1 1 calc R
H50B H 0.2744 0.6808 0.6155 0.097 Uiso 1 1 calc R
H50C H 0.2687 0.7695 0.5867 0.097 Uiso 1 1 calc R
C51 C 0.8147(4) 0.8322(4) 0.5248(2) 0.0247(11) Uani 1 1 d .
C52 C 0.7752(5) 0.8753(4) 0.4816(2) 0.0338(13) Uani 1 1 d .
C53 C 0.8451(5) 0.9018(4) 0.4405(2) 0.0389(14) Uani 1 1 d .
H53 H 0.8220 0.9299 0.4108 0.047 Uiso 1 1 calc R
C54 C 0.9469(5) 0.8877(4) 0.4427(2) 0.0388(14) Uani 1 1 d .
H54 H 0.9914 0.9059 0.4143 0.047 Uiso 1 1 calc R
C55 C 0.9854(5) 0.8472(4) 0.4863(3) 0.0386(14) Uani 1 1 d .
H55 H 1.0558 0.8394 0.4874 0.046 Uiso 1 1 calc R
C56 C 0.9176(4) 0.8174(4) 0.5292(2) 0.0316(12) Uani 1 1 d .
C57 C 0.6634(5) 0.8943(5) 0.4806(3) 0.0473(16) Uani 1 1 d .
H57 H 0.6224 0.8598 0.5086 0.057 Uiso 1 1 calc R
C58 C 0.6843(6) 1.0060(6) 0.5009(4) 0.064(2) Uani 1 1 d .
H58A H 0.7207 1.0291 0.5417 0.096 Uiso 1 1 calc R
H58B H 0.6129 1.0164 0.4967 0.096 Uiso 1 1 calc R
H58C H 0.7325 1.0428 0.4772 0.096 Uiso 1 1 calc R
C59 C 0.5870(7) 0.8525(7) 0.4198(4) 0.078(3) Uani 1 1 d .
H59A H 0.6260 0.8838 0.3911 0.118 Uiso 1 1 calc R
H59B H 0.5179 0.8665 0.4213 0.118 Uiso 1 1 calc R
H59C H 0.5690 0.7811 0.4087 0.118 Uiso 1 1 calc R
C60 C 0.9618(5) 0.7767(5) 0.5785(3) 0.0401(14) Uani 1 1 d .
H60 H 0.9003 0.7555 0.6011 0.048 Uiso 1 1 calc R
C61 C 0.9876(7) 0.6828(6) 0.5526(3) 0.0607(19) Uani 1 1 d .
H61A H 1.0465 0.7005 0.5292 0.091 Uiso 1 1 calc R
H61B H 0.9200 0.6330 0.5281 0.091 Uiso 1 1 calc R
H61C H 1.0125 0.6563 0.5842 0.091 Uiso 1 1 calc R
C62 C 1.0607(6) 0.8540(6) 0.6203(3) 0.0598(19) Uani 1 1 d .
H62A H 1.1234 0.8757 0.5998 0.090 Uiso 1 1 calc R
H62B H 1.0825 0.8258 0.6519 0.090 Uiso 1 1 calc R
H62C H 1.0403 0.9104 0.6364 0.090 Uiso 1 1 calc R
N1 N 0.8469(3) 0.2441(3) 0.85824(17) 0.0235(9) Uani 1 1 d .
N2 N 0.7468(3) 0.2108(3) 0.93494(17) 0.0242(9) Uani 1 1 d .
N3 N 0.6360(3) 0.7600(3) 0.64071(17) 0.0242(9) Uani 1 1 d .
N4 N 0.7391(3) 0.7958(3) 0.56496(17) 0.0240(9) Uani 1 1 d .
I1 I 0.64583(3) 0.02961(3) 0.820552(15) 0.03562(11) Uani 1 1 d .
I2 I 0.82476(3) 0.98183(3) 0.675445(16) 0.04229(12) Uani 1 1 d .
I3 I 0.08371(5) 0.44265(4) 0.60957(2) 0.06281(15) Uani 1 1 d .
I4 I 0.09521(4) 0.57825(3) 0.716132(18) 0.04757(13) Uani 1 1 d .
I5 I 0.12377(5) 0.72691(4) 0.82909(2) 0.06247(15) Uani 1 1 d .
I6 I 0.22500(4) 0.92767(4) 0.786711(17) 0.05192(14) Uani 1 1 d .
I7 I 0.31272(5) 1.09857(4) 0.74315(2) 0.06506(16) Uani 1 1 d .
B1 B 0.7545(5) 0.1699(4) 0.8752(2) 0.0269(12) Uani 1 1 d .
B2 B 0.7255(5) 0.8368(4) 0.6238(2) 0.0257(12) Uani 1 1 d .
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'
C C 0.0033 0.0016 '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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C5 109.3(4) . .
N1 C1 C2 139.7(4) . .
C5 C1 C2 111.0(4) . .
C7 C2 C1 141.7(5) 2_767 .
C7 C2 C3 116.4(4) 2_767 .
C1 C2 C3 101.9(4) . .
C3 C3 C4 122.3(6) 2_767 .
C3 C3 C2 122.7(6) 2_767 .
C4 C3 C2 115.0(4) . .
C6 C4 C3 116.9(4) . .
C6 C4 C5 140.9(5) . .
C3 C4 C5 102.2(4) . .
N2 C5 C1 110.3(4) . .
N2 C5 C4 139.9(4) . .
C1 C5 C4 109.9(4) . .
C4 C6 C7 121.2(4) . .
C4 C6 H6 119.4 . .
C7 C6 H6 119.4 . .
C2 C7 C6 120.4(4) 2_767 .
C2 C7 H7 119.8 2_767 .
C6 C7 H7 119.8 . .
C9 C8 C13 122.9(5) . .
C9 C8 N1 119.0(5) . .
C13 C8 N1 117.9(5) . .
C8 C9 C10 117.4(5) . .
C8 C9 C14 122.1(5) . .
C10 C9 C14 120.4(5) . .
C11 C10 C9 121.2(6) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C12 C11 C10 120.2(5) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C11 C12 C13 122.7(6) . .
C11 C12 H12 118.6 . .
C13 C12 H12 118.6 . .
C12 C13 C8 115.6(5) . .
C12 C13 C17 122.6(5) . .
C8 C13 C17 121.8(5) . .
C15 C14 C9 109.3(5) . .
C15 C14 C16 110.3(6) . .
C9 C14 C16 113.3(5) . .
C15 C14 H14 107.9 . .
C9 C14 H14 107.9 . .
C16 C14 H14 107.9 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C14 C16 H16A 109.5 . .
C14 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C14 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C19 109.8(6) . .
C18 C17 C13 111.0(5) . .
C19 C17 C13 112.5(5) . .
C18 C17 H17 107.8 . .
C19 C17 H17 107.8 . .
C13 C17 H17 107.8 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C25 C20 C21 123.6(5) . .
C25 C20 N2 119.1(5) . .
C21 C20 N2 117.1(5) . .
C20 C21 C22 116.7(5) . .
C20 C21 C26 122.6(4) . .
C22 C21 C26 120.5(5) . .
C23 C22 C21 121.3(6) . .
C23 C22 H22 119.3 . .
C21 C22 H22 119.3 . .
C22 C23 C24 119.9(5) . .
C22 C23 H23 120.1 . .
C24 C23 H23 120.1 . .
C23 C24 C25 121.4(6) . .
C23 C24 H24 119.3 . .
C25 C24 H24 119.3 . .
C20 C25 C24 117.1(5) . .
C20 C25 C29 121.4(5) . .
C24 C25 C29 121.5(5) . .
C27 C26 C21 113.0(5) . .
C27 C26 C28 109.6(6) . .
C21 C26 C28 111.8(5) . .
C27 C26 H26 107.4 . .
C21 C26 H26 107.4 . .
C28 C26 H26 107.4 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C26 C28 H28A 109.5 . .
C26 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C26 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C30 C29 C25 113.9(6) . .
C30 C29 C31 109.7(6) . .
C25 C29 C31 108.9(5) . .
C30 C29 H29 108.1 . .
C25 C29 H29 108.1 . .
C31 C29 H29 108.1 . .
C29 C30 H30A 109.5 . .
C29 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C29 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C29 C31 H31A 109.5 . .
C29 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C29 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
N3 C32 C38 109.4(4) . .
N3 C32 C33 140.3(4) . .
C38 C32 C33 110.3(4) . .
C34 C33 C37 116.6(4) . .
C34 C33 C32 141.5(5) . .
C37 C33 C32 101.9(4) . .
C33 C34 C35 121.0(5) . 2_666
C33 C34 H34 119.5 . .
C35 C34 H34 119.5 2_666 .
C36 C35 C34 120.2(4) . 2_666
C36 C35 H35 119.9 . .
C34 C35 H35 119.9 2_666 .
C35 C36 C37 117.3(4) . .
C35 C36 C38 140.9(4) . .
C37 C36 C38 101.8(4) . .
C37 C37 C36 122.4(6) 2_666 .
C37 C37 C33 122.5(6) 2_666 .
C36 C37 C33 115.1(4) . .
N4 C38 C32 110.2(4) . .
N4 C38 C36 138.9(4) . .
C32 C38 C36 110.9(4) . .
C44 C39 C40 122.5(5) . .
C44 C39 N3 118.6(4) . .
C40 C39 N3 118.9(5) . .
C41 C40 C39 117.6(5) . .
C41 C40 C45 120.1(5) . .
C39 C40 C45 122.3(5) . .
C42 C41 C40 121.4(5) . .
C42 C41 H41 119.3 . .
C40 C41 H41 119.3 . .
C41 C42 C43 119.5(5) . .
C41 C42 H42 120.3 . .
C43 C42 H42 120.3 . .
C44 C43 C42 121.6(6) . .
C44 C43 H43 119.2 . .
C42 C43 H43 119.2 . .
C43 C44 C39 117.4(5) . .
C43 C44 C48 120.3(5) . .
C39 C44 C48 122.2(5) . .
C46 C45 C47 111.7(6) . .
C46 C45 C40 112.1(6) . .
C47 C45 C40 111.4(6) . .
C46 C45 H45 107.1 . .
C47 C45 H45 107.1 . .
C40 C45 H45 107.1 . .
C45 C46 H46A 109.5 . .
C45 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C45 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C45 C47 H47A 109.5 . .
C45 C47 H47B 109.5 . .
H47A C47 H47B 109.5 . .
C45 C47 H47C 109.5 . .
H47A C47 H47C 109.5 . .
H47B C47 H47C 109.5 . .
C50 C48 C44 113.4(5) . .
C50 C48 C49 109.7(6) . .
C44 C48 C49 109.1(5) . .
C50 C48 H48 108.1 . .
C44 C48 H48 108.1 . .
C49 C48 H48 108.1 . .
C48 C49 H49A 109.5 . .
C48 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C48 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
C48 C50 H50A 109.5 . .
C48 C50 H50B 109.5 . .
H50A C50 H50B 109.5 . .
C48 C50 H50C 109.5 . .
H50A C50 H50C 109.5 . .
H50B C50 H50C 109.5 . .
C56 C51 C52 124.3(5) . .
C56 C51 N4 118.2(5) . .
C52 C51 N4 117.4(5) . .
C53 C52 C51 116.2(5) . .
C53 C52 C57 121.7(5) . .
C51 C52 C57 122.1(5) . .
C54 C53 C52 121.5(6) . .
C54 C53 H53 119.3 . .
C52 C53 H53 119.3 . .
C53 C54 C55 121.5(5) . .
C53 C54 H54 119.3 . .
C55 C54 H54 119.3 . .
C54 C55 C56 119.9(6) . .
C54 C55 H55 120.0 . .
C56 C55 H55 120.0 . .
C51 C56 C55 116.5(5) . .
C51 C56 C60 123.4(5) . .
C55 C56 C60 120.0(5) . .
C58 C57 C52 111.2(5) . .
C58 C57 C59 109.9(6) . .
C52 C57 C59 112.6(6) . .
C58 C57 H57 107.7 . .
C52 C57 H57 107.7 . .
C59 C57 H57 107.7 . .
C57 C58 H58A 109.5 . .
C57 C58 H58B 109.5 . .
H58A C58 H58B 109.5 . .
C57 C58 H58C 109.5 . .
H58A C58 H58C 109.5 . .
H58B C58 H58C 109.5 . .
C57 C59 H59A 109.5 . .
C57 C59 H59B 109.5 . .
H59A C59 H59B 109.5 . .
C57 C59 H59C 109.5 . .
H59A C59 H59C 109.5 . .
H59B C59 H59C 109.5 . .
C62 C60 C56 112.6(6) . .
C62 C60 C61 112.2(6) . .
C56 C60 C61 110.3(5) . .
C62 C60 H60 107.1 . .
C56 C60 H60 107.1 . .
C61 C60 H60 107.1 . .
C60 C61 H61A 109.5 . .
C60 C61 H61B 109.5 . .
H61A C61 H61B 109.5 . .
C60 C61 H61C 109.5 . .
H61A C61 H61C 109.5 . .
H61B C61 H61C 109.5 . .
C60 C62 H62A 109.5 . .
C60 C62 H62B 109.5 . .
H62A C62 H62B 109.5 . .
C60 C62 H62C 109.5 . .
H62A C62 H62C 109.5 . .
H62B C62 H62C 109.5 . .
C1 N1 B1 106.5(4) . .
C1 N1 C8 120.7(4) . .
B1 N1 C8 132.0(4) . .
C5 N2 B1 106.5(4) . .
C5 N2 C20 120.2(4) . .
B1 N2 C20 132.6(4) . .
C32 N3 B2 106.6(4) . .
C32 N3 C39 121.2(4) . .
B2 N3 C39 131.9(4) . .
C38 N4 B2 106.2(4) . .
C38 N4 C51 119.0(4) . .
B2 N4 C51 134.8(4) . .
I3 I4 I5 176.28(2) . .
I4 I5 I6 99.47(3) . .
I7 I6 I5 176.88(2) . .
N2 B1 N1 107.4(4) . .
N2 B1 I1 126.5(4) . .
N1 B1 I1 126.1(4) . .
N3 B2 N4 107.6(4) . .
N3 B2 I2 127.2(4) . .
N4 B2 I2 125.1(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.370(6) .
C1 C5 1.399(7) .
C1 C2 1.436(7) .
C2 C7 1.400(7) 2_767
C2 C3 1.437(7) .
C3 C3 1.329(10) 2_767
C3 C4 1.419(7) .
C4 C6 1.395(7) .
C4 C5 1.455(7) .
C5 N2 1.362(6) .
C6 C7 1.432(7) .
C6 H6 0.9300 .
C7 C2 1.400(7) 2_767
C7 H7 0.9300 .
C8 C9 1.375(8) .
C8 C13 1.424(7) .
C8 N1 1.450(6) .
C9 C10 1.394(8) .
C9 C14 1.525(8) .
C10 C11 1.372(9) .
C10 H10 0.9300 .
C11 C12 1.349(9) .
C11 H11 0.9300 .
C12 C13 1.389(8) .
C12 H12 0.9300 .
C13 C17 1.518(9) .
C14 C15 1.513(10) .
C14 C16 1.541(9) .
C14 H14 0.9800 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 C18 1.505(10) .
C17 C19 1.508(9) .
C17 H17 0.9800 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 C25 1.383(8) .
C20 C21 1.391(8) .
C20 N2 1.466(6) .
C21 C22 1.397(7) .
C21 C26 1.529(8) .
C22 C23 1.373(9) .
C22 H22 0.9300 .
C23 C24 1.380(9) .
C23 H23 0.9300 .
C24 C25 1.388(8) .
C24 H24 0.9300 .
C25 C29 1.537(9) .
C26 C27 1.521(9) .
C26 C28 1.539(9) .
C26 H26 0.9800 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 C30 1.520(10) .
C29 C31 1.541(9) .
C29 H29 0.9800 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
C31 H31A 0.9600 .
C31 H31B 0.9600 .
C31 H31C 0.9600 .
C32 N3 1.379(6) .
C32 C38 1.399(7) .
C32 C33 1.446(7) .
C33 C34 1.388(7) .
C33 C37 1.436(7) .
C34 C35 1.439(7) 2_666
C34 H34 0.9300 .
C35 C36 1.385(7) .
C35 C34 1.439(7) 2_666
C35 H35 0.9300 .
C36 C37 1.428(7) .
C36 C38 1.446(7) .
C37 C37 1.313(10) 2_666
C38 N4 1.378(6) .
C39 C44 1.390(8) .
C39 C40 1.407(7) .
C39 N3 1.445(6) .
C40 C41 1.385(8) .
C40 C45 1.528(9) .
C41 C42 1.379(9) .
C41 H41 0.9300 .
C42 C43 1.390(9) .
C42 H42 0.9300 .
C43 C44 1.387(8) .
C43 H43 0.9300 .
C44 C48 1.518(8) .
C45 C46 1.488(10) .
C45 C47 1.527(10) .
C45 H45 0.9800 .
C46 H46A 0.9600 .
C46 H46B 0.9600 .
C46 H46C 0.9600 .
C47 H47A 0.9600 .
C47 H47B 0.9600 .
C47 H47C 0.9600 .
C48 C50 1.508(9) .
C48 C49 1.521(10) .
C48 H48 0.9800 .
C49 H49A 0.9600 .
C49 H49B 0.9600 .
C49 H49C 0.9600 .
C50 H50A 0.9600 .
C50 H50B 0.9600 .
C50 H50C 0.9600 .
C51 C56 1.381(8) .
C51 C52 1.407(8) .
C51 N4 1.446(6) .
C52 C53 1.388(8) .
C52 C57 1.523(9) .
C53 C54 1.362(9) .
C53 H53 0.9300 .
C54 C55 1.381(9) .
C54 H54 0.9300 .
C55 C56 1.418(8) .
C55 H55 0.9300 .
C56 C60 1.517(8) .
C57 C58 1.522(10) .
C57 C59 1.528(10) .
C57 H57 0.9800 .
C58 H58A 0.9600 .
C58 H58B 0.9600 .
C58 H58C 0.9600 .
C59 H59A 0.9600 .
C59 H59B 0.9600 .
C59 H59C 0.9600 .
C60 C62 1.483(9) .
C60 C61 1.533(10) .
C60 H60 0.9800 .
C61 H61A 0.9600 .
C61 H61B 0.9600 .
C61 H61C 0.9600 .
C62 H62A 0.9600 .
C62 H62B 0.9600 .
C62 H62C 0.9600 .
N1 B1 1.446(7) .
N2 B1 1.439(7) .
N3 B2 1.444(7) .
N4 B2 1.445(7) .
I1 B1 2.122(6) .
I2 B2 2.115(6) .
I3 I4 2.8347(8) .
I4 I5 2.9929(9) .
I5 I6 3.1404(11) .
I6 I7 2.7710(11) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C7 -0.5(13) . 2_767
C5 C1 C2 C7 179.7(7) . 2_767
N1 C1 C2 C3 179.2(6) . .
C5 C1 C2 C3 -0.6(6) . .
C7 C2 C3 C3 -0.5(9) 2_767 2_767
C1 C2 C3 C3 179.7(7) . 2_767
C7 C2 C3 C4 -179.8(5) 2_767 .
C1 C2 C3 C4 0.4(6) . .
C3 C3 C4 C6 1.6(9) 2_767 .
C2 C3 C4 C6 -179.1(5) . .
C3 C3 C4 C5 -179.4(7) 2_767 .
C2 C3 C4 C5 -0.1(6) . .
N1 C1 C5 N2 1.4(6) . .
C2 C1 C5 N2 -178.8(4) . .
N1 C1 C5 C4 -179.3(4) . .
C2 C1 C5 C4 0.5(6) . .
C6 C4 C5 N2 -2.7(13) . .
C3 C4 C5 N2 178.7(7) . .
C6 C4 C5 C1 178.3(7) . .
C3 C4 C5 C1 -0.3(6) . .
C3 C4 C6 C7 -2.3(8) . .
C5 C4 C6 C7 179.3(6) . .
C4 C6 C7 C2 2.2(8) . 2_767
C13 C8 C9 C10 -1.2(8) . .
N1 C8 C9 C10 -176.7(5) . .
C13 C8 C9 C14 -177.1(5) . .
N1 C8 C9 C14 7.4(8) . .
C8 C9 C10 C11 2.0(9) . .
C14 C9 C10 C11 178.0(6) . .
C9 C10 C11 C12 -1.6(9) . .
C10 C11 C12 C13 0.4(9) . .
C11 C12 C13 C8 0.4(8) . .
C11 C12 C13 C17 178.5(5) . .
C9 C8 C13 C12 0.1(7) . .
N1 C8 C13 C12 175.6(4) . .
C9 C8 C13 C17 -178.1(5) . .
N1 C8 C13 C17 -2.6(7) . .
C8 C9 C14 C15 93.5(7) . .
C10 C9 C14 C15 -82.3(7) . .
C8 C9 C14 C16 -143.0(6) . .
C10 C9 C14 C16 41.2(8) . .
C12 C13 C17 C18 -67.2(8) . .
C8 C13 C17 C18 110.9(7) . .
C12 C13 C17 C19 56.3(7) . .
C8 C13 C17 C19 -125.7(6) . .
C25 C20 C21 C22 -2.1(7) . .
N2 C20 C21 C22 174.2(4) . .
C25 C20 C21 C26 -177.0(5) . .
N2 C20 C21 C26 -0.7(7) . .
C20 C21 C22 C23 1.1(8) . .
C26 C21 C22 C23 176.1(5) . .
C21 C22 C23 C24 -0.3(8) . .
C22 C23 C24 C25 0.3(8) . .
C21 C20 C25 C24 2.2(8) . .
N2 C20 C25 C24 -174.0(4) . .
C21 C20 C25 C29 -176.7(5) . .
N2 C20 C25 C29 7.1(7) . .
C23 C24 C25 C20 -1.2(8) . .
C23 C24 C25 C29 177.7(5) . .
C20 C21 C26 C27 -132.6(6) . .
C22 C21 C26 C27 52.8(7) . .
C20 C21 C26 C28 103.2(7) . .
C22 C21 C26 C28 -71.4(7) . .
C20 C25 C29 C30 -154.3(6) . .
C24 C25 C29 C30 26.8(8) . .
C20 C25 C29 C31 82.9(7) . .
C24 C25 C29 C31 -95.9(7) . .
N3 C32 C33 C34 1.6(14) . .
C38 C32 C33 C34 -178.8(8) . .
N3 C32 C33 C37 -179.7(7) . .
C38 C32 C33 C37 -0.1(6) . .
C37 C33 C34 C35 1.1(9) . 2_666
C32 C33 C34 C35 179.7(7) . 2_666
C34 C35 C36 C37 1.6(8) 2_666 .
C34 C35 C36 C38 178.2(7) 2_666 .
C35 C36 C37 C37 -1.8(11) . 2_666
C38 C36 C37 C37 -179.6(8) . 2_666
C35 C36 C37 C33 178.7(5) . .
C38 C36 C37 C33 0.9(7) . .
C34 C33 C37 C37 -0.9(11) . 2_666
C32 C33 C37 C37 180.0(8) . 2_666
C34 C33 C37 C36 178.6(5) . .
C32 C33 C37 C36 -0.5(7) . .
N3 C32 C38 N4 -0.7(6) . .
C33 C32 C38 N4 179.6(5) . .
N3 C32 C38 C36 -179.6(5) . .
C33 C32 C38 C36 0.6(7) . .
C35 C36 C38 N4 3.7(14) . .
C37 C36 C38 N4 -179.3(7) . .
C35 C36 C38 C32 -177.8(7) . .
C37 C36 C38 C32 -0.9(6) . .
C44 C39 C40 C41 2.6(8) . .
N3 C39 C40 C41 -175.7(5) . .
C44 C39 C40 C45 -179.3(5) . .
N3 C39 C40 C45 2.5(7) . .
C39 C40 C41 C42 -0.2(8) . .
C45 C40 C41 C42 -178.4(5) . .
C40 C41 C42 C43 -1.4(9) . .
C41 C42 C43 C44 0.6(9) . .
C42 C43 C44 C39 1.6(8) . .
C42 C43 C44 C48 -177.7(5) . .
C40 C39 C44 C43 -3.3(8) . .
N3 C39 C44 C43 175.0(5) . .
C40 C39 C44 C48 176.0(5) . .
N3 C39 C44 C48 -5.7(7) . .
C41 C40 C45 C46 72.1(7) . .
C39 C40 C45 C46 -106.0(7) . .
C41 C40 C45 C47 -54.0(8) . .
C39 C40 C45 C47 127.9(6) . .
C43 C44 C48 C50 -36.1(8) . .
C39 C44 C48 C50 144.7(6) . .
C43 C44 C48 C49 86.6(7) . .
C39 C44 C48 C49 -92.7(7) . .
C56 C51 C52 C53 1.5(8) . .
N4 C51 C52 C53 -174.7(5) . .
C56 C51 C52 C57 -177.1(5) . .
N4 C51 C52 C57 6.7(8) . .
C51 C52 C53 C54 -0.8(8) . .
C57 C52 C53 C54 177.8(6) . .
C52 C53 C54 C55 -0.5(9) . .
C53 C54 C55 C56 1.2(9) . .
C52 C51 C56 C55 -0.9(8) . .
N4 C51 C56 C55 175.3(5) . .
C52 C51 C56 C60 176.1(5) . .
N4 C51 C56 C60 -7.8(8) . .
C54 C55 C56 C51 -0.5(8) . .
C54 C55 C56 C60 -177.6(5) . .
C53 C52 C57 C58 -71.8(8) . .
C51 C52 C57 C58 106.7(7) . .
C53 C52 C57 C59 52.0(8) . .
C51 C52 C57 C59 -129.6(6) . .
C51 C56 C60 C62 -109.7(6) . .
C55 C56 C60 C62 67.1(7) . .
C51 C56 C60 C61 124.1(6) . .
C55 C56 C60 C61 -59.1(7) . .
C5 C1 N1 B1 -1.3(6) . .
C2 C1 N1 B1 178.9(7) . .
C5 C1 N1 C8 -172.4(4) . .
C2 C1 N1 C8 7.8(10) . .
C9 C8 N1 C1 71.6(6) . .
C13 C8 N1 C1 -104.1(6) . .
C9 C8 N1 B1 -96.9(7) . .
C13 C8 N1 B1 87.4(7) . .
C1 C5 N2 B1 -0.8(6) . .
C4 C5 N2 B1 -179.8(7) . .
C1 C5 N2 C20 171.4(5) . .
C4 C5 N2 C20 -7.6(10) . .
C25 C20 N2 C5 75.3(6) . .
C21 C20 N2 C5 -101.1(6) . .
C25 C20 N2 B1 -114.8(6) . .
C21 C20 N2 B1 68.7(7) . .
C38 C32 N3 B2 1.6(6) . .
C33 C32 N3 B2 -178.8(7) . .
C38 C32 N3 C39 176.3(5) . .
C33 C32 N3 C39 -4.1(10) . .
C44 C39 N3 C32 -74.9(6) . .
C40 C39 N3 C32 103.4(6) . .
C44 C39 N3 B2 98.3(7) . .
C40 C39 N3 B2 -83.4(7) . .
C32 C38 N4 B2 -0.5(6) . .
C36 C38 N4 B2 178.0(7) . .
C32 C38 N4 C51 178.8(5) . .
C36 C38 N4 C51 -2.8(10) . .
C56 C51 N4 C38 -91.2(6) . .
C52 C51 N4 C38 85.2(6) . .
C56 C51 N4 B2 87.8(7) . .
C52 C51 N4 B2 -95.8(7) . .
I3 I4 I5 I6 62.4(3) . .
I4 I5 I6 I7 4.0(4) . .
C5 N2 B1 N1 0.0(6) . .
C20 N2 B1 N1 -170.9(5) . .
C5 N2 B1 I1 -177.5(4) . .
C20 N2 B1 I1 11.6(9) . .
C1 N1 B1 N2 0.8(6) . .
C8 N1 B1 N2 170.5(5) . .
C1 N1 B1 I1 178.3(4) . .
C8 N1 B1 I1 -12.0(9) . .
C32 N3 B2 N4 -1.8(6) . .
C39 N3 B2 N4 -175.8(5) . .
C32 N3 B2 I2 -179.8(4) . .
C39 N3 B2 I2 6.3(9) . .
C38 N4 B2 N3 1.4(6) . .
C51 N4 B2 N3 -177.7(5) . .
C38 N4 B2 I2 179.4(4) . .
C51 N4 B2 I2 0.3(9) . .
