#------------------------------------------------------------------------------
#$Date: 2016-07-04 15:37:58 +0300 (Mon, 04 Jul 2016) $
#$Revision: 184166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032015.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_4032015
loop_
_publ_author_name
'Matsumoto, Shoji'
'Kikuchi, Shu'
'Norita, Naoto'
'Masu, Hyuma'
'Akazome, Motohiro'
_publ_section_title
;
 Formation of Benzimidazoisoquinolinium and Benzimidazoisoindolinum Cyclic
 Systems by the Reaction of 2-(2-Alkynylphenyl)benzimidazoles with Iodine
 and Iodine-Iodine Interaction Including Halogen Bonding in Their Crystal
 Structures.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5322
_journal_page_last               5329
_journal_paper_doi               10.1021/acs.joc.6b00607
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C39.5 H30.5 I2 N4.5'
_chemical_formula_weight         821.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 91.1060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9120(3)
_cell_length_b                   10.0998(3)
_cell_length_c                   38.1226(12)
_cell_measurement_reflns_used    9560
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.3712
_cell_measurement_theta_min      4.5291
_cell_volume                     3430.75(19)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            28269
_diffrn_reflns_theta_full        68.443
_diffrn_reflns_theta_max         68.443
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    14.661
_exptl_absorpt_correction_T_max  0.32
_exptl_absorpt_correction_T_min  0.17
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.784
_refine_diff_density_min         -1.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6266
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+27.1241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                6182
_reflns_number_total             6266
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b00607_si_007.cif
_cod_data_source_block           2a_I
_cod_original_formula_sum        'C39.50 H30.50 I2 N4.50'
_cod_database_code               4032015
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'
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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N5 0.554(2) 0.369(2) 0.4892(5) 0.093(10) Uani d . P D 0.5 A 1
C C41 0.565(2) 0.3747(16) 0.5022(5) 0.073(10) Uani d . P D 0.5 A 2
H H41 0.6114 0.2927 0.5078 0.088 Uiso calc U P R 0.5 A 2
C C1 0.6560(6) 0.2838(6) 0.33655(15) 0.0232(12) Uani d . . . 1 . .
C C2 0.5686(7) 0.2816(6) 0.30424(15) 0.0235(12) Uani d . . . 1 . .
C C3 0.6073(7) 0.3549(7) 0.27432(17) 0.0332(15) Uani d . . . 1 . .
H H3 0.6931 0.4108 0.2749 0.04 Uiso calc U . R 1 . .
C C4 0.5199(6) 0.3451(6) 0.24407(13) 0.0206(12) Uani d . . . 1 . .
H H4 0.5414 0.3984 0.2243 0.025 Uiso calc U . R 1 . .
C C5 0.4006(7) 0.2570(8) 0.24288(16) 0.0346(15) Uani d . . . 1 . .
H H5 0.3476 0.2435 0.2213 0.042 Uiso calc U . R 1 . .
C C6 0.3576(7) 0.1890(7) 0.27198(16) 0.0300(14) Uani d . . . 1 . .
H H6 0.2721 0.1329 0.2707 0.036 Uiso calc U . R 1 . .
C C7 0.4387(7) 0.2013(6) 0.30397(15) 0.0234(12) Uani d . . . 1 . .
C C8 0.3938(6) 0.1376(6) 0.33596(15) 0.0226(12) Uani d . . . 1 . .
C C9 0.4751(6) 0.1465(6) 0.36586(15) 0.0222(12) Uani d . . . 1 . .
C C10 0.4350(6) 0.0826(6) 0.39959(15) 0.0249(13) Uani d . . . 1 . .
C C11 0.4865(9) -0.0437(7) 0.40682(18) 0.0400(17) Uani d . . . 1 . .
H H11 0.5478 -0.0884 0.3905 0.048 Uiso calc U . R 1 . .
C C12 0.4483(10) -0.1054(8) 0.4382(2) 0.050(2) Uani d . . . 1 . .
H H12 0.484 -0.192 0.4433 0.06 Uiso calc U . R 1 . .
C C13 0.3579(9) -0.0399(8) 0.46176(18) 0.0473(19) Uani d . . . 1 . .
H H13 0.3323 -0.0816 0.4832 0.057 Uiso calc U . R 1 . .
C C14 0.3056(8) 0.0844(8) 0.45434(18) 0.0402(17) Uani d . . . 1 . .
H H14 0.243 0.1284 0.4705 0.048 Uiso calc U . R 1 . .
C C15 0.3432(7) 0.1466(7) 0.42331(16) 0.0318(14) Uani d . . . 1 . .
H H15 0.3064 0.2329 0.4183 0.038 Uiso calc U . R 1 . .
C C16 0.7180(6) 0.2368(6) 0.39284(15) 0.0251(13) Uani d . . . 1 . .
C C17 0.7288(7) 0.1942(8) 0.42749(16) 0.0342(15) Uani d . . . 1 . .
H H17 0.6513 0.1441 0.4379 0.041 Uiso calc U . R 1 . .
C C18 0.8569(8) 0.2283(8) 0.44587(18) 0.0393(17) Uani d . . . 1 . .
H H18 0.868 0.2002 0.4696 0.047 Uiso calc U . R 1 . .
C C19 0.9711(7) 0.3024(8) 0.43111(18) 0.0379(16) Uani d . . . 1 . .
H H19 1.0576 0.3234 0.445 0.045 Uiso calc U . R 1 . .
C C20 0.9617(7) 0.3459(7) 0.39690(17) 0.0339(15) Uani d . . . 1 . .
H H20 1.0396 0.3959 0.3866 0.041 Uiso calc U . R 1 . .
C C21 0.8311(7) 0.3123(7) 0.37836(15) 0.0268(13) Uani d . . . 1 . .
C C22 0.8864(7) 0.4101(6) 0.31981(15) 0.0264(13) Uani d . . . 1 . .
C C23 0.9600(7) 0.3374(7) 0.29460(16) 0.0309(14) Uani d . . . 1 . .
H H23 0.952 0.2436 0.2939 0.037 Uiso calc U . R 1 . .
C C24 1.0454(8) 0.4046(8) 0.27049(17) 0.0381(17) Uani d . . . 1 . .
H H24 1.0933 0.357 0.2524 0.046 Uiso calc U . R 1 . .
C C25 1.0616(8) 0.5400(8) 0.27256(19) 0.0409(17) Uani d . . . 1 . .
H H25 1.1217 0.585 0.2561 0.049 Uiso calc U . R 1 . .
C C26 0.9904(8) 0.6113(7) 0.2986(2) 0.0421(17) Uani d . . . 1 . .
H H26 1.0027 0.7046 0.3002 0.05 Uiso calc U . R 1 . .
C C27 0.9010(7) 0.5450(7) 0.32239(18) 0.0339(15) Uani d . . . 1 . .
H H27 0.8507 0.5925 0.3402 0.041 Uiso calc U . R 1 . .
C C28 0.3973(11) 0.5964(9) 0.3350(2) 0.060(2) Uani d . . . 1 . .
H H28 0.3688 0.6273 0.3123 0.072 Uiso calc U . R 1 . .
C C29 0.3177(9) 0.4994(8) 0.3511(2) 0.0473(19) Uani d . . . 1 . .
H H29 0.2355 0.4617 0.3384 0.057 Uiso calc U . R 1 . .
N N3 0.3463(8) 0.4541(7) 0.38287(18) 0.0484(16) Uani d . . . 1 . .
C C31 0.4659(10) 0.5048(9) 0.3996(2) 0.055(2) Uani d . . . 1 . .
H H31 0.4912 0.4724 0.4223 0.065 Uiso calc U . R 1 . .
C C32 0.5549(10) 0.6026(10) 0.3853(3) 0.062(3) Uani d . . . 1 . .
H H32 0.6389 0.6371 0.398 0.075 Uiso calc U . R 1 . .
C C33 0.5189(11) 0.6481(9) 0.3524(3) 0.059(2) Uani d . . . 1 . .
H H33 0.5778 0.7149 0.3418 0.071 Uiso calc U . R 1 . .
N N4 0.0758(10) 0.2459(9) 0.5245(2) 0.070(2) Uani d . . . 1 . .
C C35 -0.0186(13) 0.3373(11) 0.5351(3) 0.070(3) Uani d . . . 1 . .
H H35 -0.0424 0.409 0.5198 0.085 Uiso calc U . R 1 . .
C C36 -0.0834(13) 0.3323(10) 0.5674(3) 0.074(3) Uani d . . . 1 . .
H H36 -0.1488 0.4008 0.5747 0.088 Uiso calc U . R 1 . .
C C37 -0.0525(17) 0.2276(13) 0.5887(3) 0.095(4) Uani d . . . 1 . .
H H37 -0.0964 0.2213 0.6111 0.113 Uiso calc U . R 1 . .
C C38 0.0423(17) 0.1320(14) 0.5774(3) 0.100(5) Uani d . . . 1 . .
H H38 0.0667 0.0581 0.5919 0.12 Uiso calc U . R 1 . .
C C39 0.1009(13) 0.1444(12) 0.5453(3) 0.077(3) Uani d . . . 1 . .
H H39 0.1643 0.0756 0.5373 0.093 Uiso calc U . R 1 . .
C C40 0.4068(12) 0.3960(12) 0.5027(2) 0.070(3) Uani d . . D 1 . .
H H40 0.345 0.3223 0.5081 0.084 Uiso calc U . R 1 A 1
C C42 0.6452(12) 0.4908(13) 0.4922(4) 0.088(4) Uani d . . D 1 . .
H H42 0.7509 0.4825 0.4901 0.106 Uiso calc U . R 1 A 1
I I1 0.80561(4) 0.95028(4) 0.32864(2) 0.02985(12) Uani d . . . 1 . .
I I2 0.18393(4) 0.03904(4) 0.33640(2) 0.03113(13) Uani d . . . 1 . .
N N1 0.6083(5) 0.2201(5) 0.36572(12) 0.0218(10) Uani d . . . 1 . .
N N2 0.7903(6) 0.3413(5) 0.34372(13) 0.0266(11) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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_site_symmetry_1
_geom_angle
C40 N5 C42 . 108.6(14)
C40 C41 C42 . 112.4(13)
C40 C41 H41 . 123.8
C42 C41 H41 . 123.8
N2 C1 N1 . 109.1(5)
N2 C1 C2 . 129.7(5)
N1 C1 C2 . 121.2(5)
C3 C2 C7 . 120.6(6)
C3 C2 C1 . 123.1(6)
C7 C2 C1 . 116.3(5)
C4 C3 C2 . 119.7(6)
C4 C3 H3 . 120.2
C2 C3 H3 . 120.2
C3 C4 C5 . 119.5(5)
C3 C4 H4 . 120.2
C5 C4 H4 . 120.2
C6 C5 C4 . 121.5(6)
C6 C5 H5 . 119.2
C4 C5 H5 . 119.2
C5 C6 C7 . 120.7(6)
C5 C6 H6 . 119.6
C7 C6 H6 . 119.6
C6 C7 C2 . 117.5(5)
C6 C7 C8 . 123.1(6)
C2 C7 C8 . 119.4(5)
C9 C8 C7 . 122.3(5)
C9 C8 I2 . 119.1(4)
C7 C8 I2 . 118.4(4)
C8 C9 N1 . 118.4(5)
C8 C9 C10 . 124.8(5)
N1 C9 C10 . 116.8(5)
C11 C10 C15 . 119.8(6)
C11 C10 C9 . 119.2(5)
C15 C10 C9 . 120.9(6)
C10 C11 C12 . 119.8(6)
C10 C11 H11 . 120.1
C12 C11 H11 . 120.1
C13 C12 C11 . 119.8(7)
C13 C12 H12 . 120.1
C11 C12 H12 . 120.1
C14 C13 C12 . 120.3(7)
C14 C13 H13 . 119.9
C12 C13 H13 . 119.9
C13 C14 C15 . 120.4(6)
C13 C14 H14 . 119.8
C15 C14 H14 . 119.8
C14 C15 C10 . 120.0(6)
C14 C15 H15 . 120.0
C10 C15 H15 . 120.0
C21 C16 C17 . 120.7(6)
C21 C16 N1 . 105.7(5)
C17 C16 N1 . 133.6(6)
C18 C17 C16 . 116.7(6)
C18 C17 H17 . 121.6
C16 C17 H17 . 121.6
C17 C18 C19 . 122.4(6)
C17 C18 H18 . 118.8
C19 C18 H18 . 118.8
C20 C19 C18 . 121.6(6)
C20 C19 H19 . 119.2
C18 C19 H19 . 119.2
C19 C20 C21 . 116.0(6)
C19 C20 H20 . 122.0
C21 C20 H20 . 122.0
C16 C21 C20 . 122.6(6)
C16 C21 N2 . 108.3(5)
C20 C21 N2 . 129.0(6)
C27 C22 C23 . 122.1(6)
C27 C22 N2 . 119.4(6)
C23 C22 N2 . 118.6(6)
C24 C23 C22 . 118.4(6)
C24 C23 H23 . 120.8
C22 C23 H23 . 120.8
C25 C24 C23 . 120.5(6)
C25 C24 H24 . 119.7
C23 C24 H24 . 119.7
C24 C25 C26 . 120.4(6)
C24 C25 H25 . 119.8
C26 C25 H25 . 119.8
C27 C26 C25 . 119.4(7)
C27 C26 H26 . 120.3
C25 C26 H26 . 120.3
C22 C27 C26 . 119.1(6)
C22 C27 H27 . 120.4
C26 C27 H27 . 120.4
C29 C28 C33 . 118.2(9)
C29 C28 H28 . 120.9
C33 C28 H28 . 120.9
N3 C29 C28 . 124.9(9)
N3 C29 H29 . 117.6
C28 C29 H29 . 117.6
C29 N3 C31 . 116.4(7)
N3 C31 C32 . 123.0(9)
N3 C31 H31 . 118.5
C32 C31 H31 . 118.5
C33 C32 C31 . 118.3(9)
C33 C32 H32 . 120.8
C31 C32 H32 . 120.8
C28 C33 C32 . 119.2(8)
C28 C33 H33 . 120.4
C32 C33 H33 . 120.4
C39 N4 C35 . 117.6(8)
N4 C35 C36 . 122.2(10)
N4 C35 H35 . 118.9
C36 C35 H35 . 118.9
C37 C36 C35 . 118.8(10)
C37 C36 H36 . 120.6
C35 C36 H36 . 120.6
C38 C37 C36 . 119.0(9)
C38 C37 H37 . 120.5
C36 C37 H37 . 120.5
C39 C38 C37 . 118.5(11)
C39 C38 H38 . 120.8
C37 C38 H38 . 120.8
N4 C39 C38 . 123.9(11)
N4 C39 H39 . 118.0
C38 C39 H39 . 118.0
C42 C40 C41 3_666 120.6(11)
C42 C40 N5 3_666 124.6(12)
C42 C40 H40 3_666 117.7
N5 C40 H40 . 117.7
C40 C42 C41 3_666 121.3(11)
C40 C42 N5 3_666 124.7(12)
C40 C42 H42 3_666 117.7
N5 C42 H42 . 117.7
C1 N1 C9 . 122.2(5)
C1 N1 C16 . 108.5(5)
C9 N1 C16 . 129.2(5)
C1 N2 C21 . 108.3(5)
C1 N2 C22 . 127.8(5)
C21 N2 C22 . 123.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N5 C40 . 1.447(17)
N5 C42 . 1.473(18)
C41 C40 . 1.425(17)
C41 C42 . 1.430(17)
C41 H41 . 0.95
C1 N2 . 1.353(8)
C1 N1 . 1.360(7)
C1 C2 . 1.445(8)
C2 C3 . 1.408(8)
C2 C7 . 1.413(9)
C3 C4 . 1.383(8)
C3 H3 . 0.95
C4 C5 . 1.387(9)
C4 H4 . 0.95
C5 C6 . 1.366(9)
C5 H5 . 0.95
C6 C7 . 1.411(8)
C6 H6 . 0.95
C7 C8 . 1.442(8)
C8 C9 . 1.342(8)
C8 I2 . 2.119(6)
C9 N1 . 1.401(7)
C9 C10 . 1.488(8)
C10 C11 . 1.382(9)
C10 C15 . 1.390(8)
C11 C12 . 1.396(10)
C11 H11 . 0.95
C12 C13 . 1.387(11)
C12 H12 . 0.95
C13 C14 . 1.367(11)
C13 H13 . 0.95
C14 C15 . 1.387(9)
C14 H14 . 0.95
C15 H15 . 0.95
C16 C21 . 1.387(9)
C16 C17 . 1.391(9)
C16 N1 . 1.419(7)
C17 C18 . 1.372(10)
C17 H17 . 0.95
C18 C19 . 1.391(10)
C18 H18 . 0.95
C19 C20 . 1.377(10)
C19 H19 . 0.95
C20 C21 . 1.392(9)
C20 H20 . 0.95
C21 N2 . 1.394(8)
C22 C27 . 1.372(9)
C22 C23 . 1.385(9)
C22 N2 . 1.441(7)
C23 C24 . 1.383(9)
C23 H23 . 0.95
C24 C25 . 1.378(11)
C24 H24 . 0.95
C25 C26 . 1.390(10)
C25 H25 . 0.95
C26 C27 . 1.389(10)
C26 H26 . 0.95
C27 H27 . 0.95
C28 C29 . 1.362(11)
C28 C33 . 1.363(13)
C28 H28 . 0.95
C29 N3 . 1.315(10)
C29 H29 . 0.95
N3 C31 . 1.333(11)
C31 C32 . 1.386(13)
C31 H31 . 0.95
C32 C33 . 1.366(14)
C32 H32 . 0.95
C33 H33 . 0.95
N4 C39 . 1.314(13)
N4 C35 . 1.318(13)
C35 C36 . 1.372(13)
C35 H35 . 0.95
C36 C37 . 1.359(16)
C36 H36 . 0.95
C37 C38 . 1.358(18)
C37 H37 . 0.95
C38 C39 . 1.345(14)
C38 H38 . 0.95
C39 H39 . 0.95
C40 C42 3_666 1.250(15)
C40 H40 . 0.95
C42 C40 3_666 1.250(15)
C42 H42 . 0.95
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_4
_geom_torsion
N2 C1 C2 C3 . -6.6(10)
N1 C1 C2 C3 . 174.6(6)
N2 C1 C2 C7 . 173.8(6)
N1 C1 C2 C7 . -5.0(8)
C7 C2 C3 C4 . -2.0(10)
C1 C2 C3 C4 . 178.4(6)
C2 C3 C4 C5 . -4.0(10)
C3 C4 C5 C6 . 6.7(10)
C4 C5 C6 C7 . -3.4(10)
C5 C6 C7 C2 . -2.6(9)
C5 C6 C7 C8 . 176.6(6)
C3 C2 C7 C6 . 5.2(9)
C1 C2 C7 C6 . -175.2(5)
C3 C2 C7 C8 . -174.0(6)
C1 C2 C7 C8 . 5.7(8)
C6 C7 C8 C9 . 177.6(6)
C2 C7 C8 C9 . -3.3(9)
C6 C7 C8 I2 . -7.1(8)
C2 C7 C8 I2 . 172.0(4)
C7 C8 C9 N1 . -0.2(9)
I2 C8 C9 N1 . -175.4(4)
C7 C8 C9 C10 . -179.7(6)
I2 C8 C9 C10 . 5.0(8)
C8 C9 C10 C11 . 90.1(8)
N1 C9 C10 C11 . -89.4(7)
C8 C9 C10 C15 . -88.0(8)
N1 C9 C10 C15 . 92.4(7)
C15 C10 C11 C12 . -1.1(11)
C9 C10 C11 C12 . -179.2(7)
C10 C11 C12 C13 . 0.4(13)
C11 C12 C13 C14 . 0.4(14)
C12 C13 C14 C15 . -0.5(13)
C13 C14 C15 C10 . -0.1(11)
C11 C10 C15 C14 . 1.0(10)
C9 C10 C15 C14 . 179.1(6)
C21 C16 C17 C18 . -1.3(10)
N1 C16 C17 C18 . 178.5(7)
C16 C17 C18 C19 . 0.4(11)
C17 C18 C19 C20 . 0.0(12)
C18 C19 C20 C21 . 0.6(11)
C17 C16 C21 C20 . 2.0(10)
N1 C16 C21 C20 . -177.9(6)
C17 C16 C21 N2 . -179.6(6)
N1 C16 C21 N2 . 0.5(7)
C19 C20 C21 C16 . -1.5(10)
C19 C20 C21 N2 . -179.6(6)
C27 C22 C23 C24 . -2.8(10)
N2 C22 C23 C24 . 176.4(6)
C22 C23 C24 C25 . 2.7(10)
C23 C24 C25 C26 . -0.9(11)
C24 C25 C26 C27 . -0.8(12)
C23 C22 C27 C26 . 1.1(11)
N2 C22 C27 C26 . -178.1(6)
C25 C26 C27 C22 . 0.7(11)
C33 C28 C29 N3 . 2.3(14)
C28 C29 N3 C31 . -2.6(13)
C29 N3 C31 C32 . 1.7(12)
N3 C31 C32 C33 . -0.6(13)
C29 C28 C33 C32 . -1.0(14)
C31 C32 C33 C28 . 0.2(13)
C39 N4 C35 C36 . 3.4(18)
N4 C35 C36 C37 . -1.9(18)
C35 C36 C37 C38 . 0.(2)
C36 C37 C38 C39 . -1.(2)
C35 N4 C39 C38 . -3.6(19)
C37 C38 C39 N4 . 2.(2)
C42 C41 C40 C42 3_666 -26.(2)
C42 N5 C40 C42 3_666 16.(3)
C40 C41 C42 C40 3_666 26.(2)
C40 N5 C42 C40 3_666 -16.(3)
N2 C1 N1 C9 . -177.3(5)
C2 C1 N1 C9 . 1.8(8)
N2 C1 N1 C16 . -0.5(7)
C2 C1 N1 C16 . 178.6(5)
C8 C9 N1 C1 . 0.9(8)
C10 C9 N1 C1 . -179.5(5)
C8 C9 N1 C16 . -175.2(6)
C10 C9 N1 C16 . 4.4(9)
C21 C16 N1 C1 . 0.0(6)
C17 C16 N1 C1 . -179.9(7)
C21 C16 N1 C9 . 176.4(6)
C17 C16 N1 C9 . -3.4(11)
N1 C1 N2 C21 . 0.8(7)
C2 C1 N2 C21 . -178.1(6)
N1 C1 N2 C22 . 175.0(6)
C2 C1 N2 C22 . -4.0(10)
C16 C21 N2 C1 . -0.8(7)
C20 C21 N2 C1 . 177.4(7)
C16 C21 N2 C22 . -175.3(5)
C20 C21 N2 C22 . 3.0(10)
C27 C22 N2 C1 . 108.8(8)
C23 C22 N2 C1 . -70.5(8)
C27 C22 N2 C21 . -77.8(8)
C23 C22 N2 C21 . 102.9(7)
