#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:01:37 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179737 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/33/7003360.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_7003360
loop_
_publ_author_name
'Pugh, David'
'Boyle, Aimee'
'Danopoulos, Andreas A.'
_publ_section_title
;
 ‘Pincer’ pyridine dicarbene complexes of nickel and
 their derivatives. Unusual ring opening of a coordinated
 imidazol-2-ylidene
;
_journal_issue                   8
_journal_name_full               'Dalton Transactions'
_journal_page_first              1087
_journal_page_last               1094
_journal_paper_doi               10.1039/b715769j
_journal_year                    2008
_chemical_formula_moiety         'C37 H47 N5, C H Cl3, 0.67(C H Cl3), 2(I)'
_chemical_formula_sum            'C38.67 H48.67 Cl5 I2 N5'
_chemical_formula_weight         1014.54
_chemical_name_systematic
;
?
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   52.325(4)
_cell_length_b                   52.325(4)
_cell_length_c                   9.4345(5)
_cell_measurement_reflns_used    10814
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     22370(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material
'PLATON (Spek, 2003), WinGX (Farrugia, 1999) and enCIFer (Allen et al., 2004).'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_av_sigmaI/netI    0.0986
_diffrn_reflns_limit_h_max       67
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_k_max       66
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40406
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.563
_exptl_absorpt_correction_T_max  0.7881
_exptl_absorpt_correction_T_min  0.6031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             9120
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         11431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+268.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                6384
_reflns_number_total             11431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715769j.txt
_cod_data_source_block           1MeI2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7003360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63044(16) 0.03180(15) 0.7891(6) 0.0404(16) Uani 1 1 d . . .
C2 C 0.60506(16) 0.00629(16) 0.7443(7) 0.0449(17) Uani 1 1 d . . .
C3 C 0.60690(16) -0.01915(16) 0.7299(7) 0.0458(17) Uani 1 1 d . . .
H3 H 0.5903 -0.0368 0.6968 0.055 Uiso 1 1 calc R . .
C4 C 0.63297(17) -0.01913(16) 0.7638(7) 0.0460(18) Uani 1 1 d . . .
H4 H 0.6339 -0.0368 0.7571 0.055 Uiso 1 1 calc R . .
C5 C 0.65751(15) 0.00699(15) 0.8071(7) 0.0401(16) Uani 1 1 d . . .
H5 H 0.6752 0.0070 0.8280 0.048 Uiso 1 1 calc R . .
C6 C 0.65700(15) 0.03322(14) 0.8209(6) 0.0376(15) Uani 1 1 d . . .
C7 C 0.57613(17) 0.00567(19) 0.7135(8) 0.056(2) Uani 1 1 d . . .
H7 H 0.5802 0.0265 0.7208 0.067 Uiso 1 1 calc R . .
C8 C 0.5648(2) -0.0049(2) 0.5645(9) 0.0758(9) Uani 1 1 d . . .
H8A H 0.5598 -0.0255 0.5542 0.114 Uiso 1 1 calc R . .
H8B H 0.5802 0.0073 0.4957 0.114 Uiso 1 1 calc R . .
H8C H 0.5472 -0.0032 0.5474 0.114 Uiso 1 1 calc R . .
C9 C 0.5532(2) -0.0118(2) 0.8214(9) 0.0758(9) Uani 1 1 d . . .
H9A H 0.5465 -0.0328 0.8087 0.114 Uiso 1 1 calc R . .
H9B H 0.5365 -0.0086 0.8100 0.114 Uiso 1 1 calc R . .
H9C H 0.5616 -0.0056 0.9165 0.114 Uiso 1 1 calc R . .
C10 C 0.68434(15) 0.06145(15) 0.8677(7) 0.0431(17) Uani 1 1 d . . .
H10 H 0.6820 0.0787 0.8405 0.052 Uiso 1 1 calc R . .
C11 C 0.6890(2) 0.0622(2) 1.0253(9) 0.0758(9) Uani 1 1 d . . .
H11A H 0.6712 0.0591 1.0744 0.114 Uiso 1 1 calc R . .
H11B H 0.7057 0.0814 1.0523 0.114 Uiso 1 1 calc R . .
H11C H 0.6932 0.0466 1.0519 0.114 Uiso 1 1 calc R . .
C12 C 0.7130(2) 0.0653(2) 0.7993(9) 0.0758(9) Uani 1 1 d . . .
H12A H 0.7299 0.0837 0.8326 0.114 Uiso 1 1 calc R . .
H12B H 0.7116 0.0659 0.6959 0.114 Uiso 1 1 calc R . .
H12C H 0.7156 0.0487 0.8262 0.114 Uiso 1 1 calc R . .
C13 C 0.63499(15) 0.07884(15) 0.7071(6) 0.0400(16) Uani 1 1 d . . .
H13 H 0.6402 0.0779 0.6116 0.048 Uiso 1 1 calc R . .
C14 C 0.62240(16) 0.06781(16) 0.9312(7) 0.0446(17) Uani 1 1 d . . .
H14 H 0.6175 0.0576 1.0190 0.054 Uiso 1 1 calc R . .
C15 C 0.62429(16) 0.09363(16) 0.9071(7) 0.0454(17) Uani 1 1 d . . .
H15 H 0.6207 0.1051 0.9734 0.054 Uiso 1 1 calc R . .
C16 C 0.63574(15) 0.12623(14) 0.6917(6) 0.0377(15) Uani 1 1 d . . .
C17 C 0.65898(14) 0.14271(14) 0.5979(6) 0.0367(15) Uani 1 1 d . . .
C18 C 0.65802(14) 0.16572(15) 0.5343(7) 0.0398(16) Uani 1 1 d . . .
H18 H 0.6731 0.1774 0.4682 0.048 Uiso 1 1 calc R . .
C19 C 0.63645(14) 0.17299(14) 0.5604(6) 0.0357(15) Uani 1 1 d . . .
C20 C 0.61479(14) 0.15436(14) 0.6579(6) 0.0345(15) Uani 1 1 d . . .
C21 C 0.57366(14) 0.16313(14) 0.6068(7) 0.0359(15) Uani 1 1 d . . .
H21 H 0.5762 0.1652 0.5069 0.043 Uiso 1 1 calc R . .
C22 C 0.57965(15) 0.15634(15) 0.8329(7) 0.0407(16) Uani 1 1 d . . .
H22 H 0.5873 0.1529 0.9175 0.049 Uiso 1 1 calc R . .
C23 C 0.55620(15) 0.16018(15) 0.8220(6) 0.0407(16) Uani 1 1 d . . .
H23 H 0.5442 0.1600 0.8980 0.049 Uiso 1 1 calc R . .
C24 C 0.52980(15) 0.16901(16) 0.6198(6) 0.0393(16) Uani 1 1 d . . .
C25 C 0.50428(15) 0.14457(16) 0.5704(7) 0.0419(16) Uani 1 1 d . . .
C26 C 0.48320(16) 0.14964(19) 0.5087(7) 0.0511(19) Uani 1 1 d . . .
H26 H 0.4656 0.1336 0.4722 0.061 Uiso 1 1 calc R . .
C27 C 0.48772(17) 0.1781(2) 0.5000(7) 0.051(2) Uani 1 1 d . . .
H27 H 0.4728 0.1812 0.4601 0.061 Uiso 1 1 calc R . .
C28 C 0.51315(17) 0.20161(18) 0.5476(7) 0.0493(19) Uani 1 1 d . . .
H28 H 0.5158 0.2209 0.5382 0.059 Uiso 1 1 calc R . .
C29 C 0.53558(16) 0.19818(16) 0.6102(7) 0.0427(17) Uani 1 1 d . . .
C30 C 0.49907(15) 0.11354(16) 0.5826(7) 0.0475(18) Uani 1 1 d . . .
H30 H 0.5181 0.1148 0.6104 0.057 Uiso 1 1 calc R . .
C31 C 0.4769(2) 0.0975(2) 0.6993(9) 0.0758(9) Uani 1 1 d . . .
H31A H 0.4838 0.1088 0.7876 0.114 Uiso 1 1 calc R . .
H31B H 0.4747 0.0779 0.7129 0.114 Uiso 1 1 calc R . .
H31C H 0.4578 0.0954 0.6729 0.114 Uiso 1 1 calc R . .
C32 C 0.4887(2) 0.0961(2) 0.4448(9) 0.0758(9) Uani 1 1 d . . .
H32A H 0.4697 0.0940 0.4170 0.114 Uiso 1 1 calc R . .
H32B H 0.4864 0.0765 0.4588 0.114 Uiso 1 1 calc R . .
H32C H 0.5032 0.1065 0.3701 0.114 Uiso 1 1 calc R . .
C33 C 0.56380(16) 0.22435(16) 0.6566(8) 0.0493(18) Uani 1 1 d . . .
H33 H 0.5758 0.2167 0.7034 0.059 Uiso 1 1 calc R . .
C34 C 0.5811(2) 0.2423(2) 0.5299(9) 0.0758(9) Uani 1 1 d . . .
H34A H 0.5822 0.2292 0.4587 0.114 Uiso 1 1 calc R . .
H34B H 0.6011 0.2569 0.5597 0.114 Uiso 1 1 calc R . .
H34C H 0.5713 0.2524 0.4889 0.114 Uiso 1 1 calc R . .
C35 C 0.5590(2) 0.2427(2) 0.7643(9) 0.0758(9) Uani 1 1 d . . .
H35A H 0.5461 0.2494 0.7243 0.114 Uiso 1 1 calc R . .
H35B H 0.5781 0.2598 0.7898 0.114 Uiso 1 1 calc R . .
H35C H 0.5498 0.2308 0.8492 0.114 Uiso 1 1 calc R . .
C36 C 0.68360(15) 0.13645(17) 0.5673(8) 0.0484(18) Uani 1 1 d . . .
H36A H 0.6778 0.1222 0.4895 0.073 Uiso 1 1 calc R . .
H36B H 0.6877 0.1283 0.6522 0.073 Uiso 1 1 calc R . .
H36C H 0.7014 0.1548 0.5403 0.073 Uiso 1 1 calc R . .
C37 C 0.63734(15) 0.19931(15) 0.4933(7) 0.0443(17) Uani 1 1 d . . .
H37A H 0.6577 0.2135 0.4659 0.067 Uiso 1 1 calc R . .
H37B H 0.6302 0.2085 0.5610 0.067 Uiso 1 1 calc R . .
H37C H 0.6247 0.1931 0.4089 0.067 Uiso 1 1 calc R . .
C38 C 0.1093(2) 0.2673(2) 0.9093(11) 0.080(3) Uani 1 1 d . . .
H38 H 0.0927 0.2701 0.9432 0.096 Uiso 1 1 calc R . .
C39 C 0.1844(3) 0.3842(3) 0.3252(13) 0.062(3) Uani 0.67 1 d P . .
H39 H 0.1766 0.3732 0.4162 0.074 Uiso 0.67 1 calc PR . .
N1 N 0.62882(13) 0.05842(12) 0.8075(5) 0.0404(14) Uani 1 1 d . . .
N2 N 0.63258(12) 0.10073(12) 0.7655(5) 0.0376(13) Uani 1 1 d . . .
N3 N 0.61420(11) 0.13183(11) 0.7243(5) 0.0326(12) Uani 1 1 d . . .
N4 N 0.59059(12) 0.15845(11) 0.6968(5) 0.0352(12) Uani 1 1 d . . .
N5 N 0.55267(12) 0.16446(12) 0.6805(5) 0.0363(12) Uani 1 1 d . . .
I1 I 0.628975(11) 0.067810(11) 0.32367(5) 0.04747(16) Uani 1 1 d . . .
I2 I 0.099632(11) 0.164328(13) 0.11597(5) 0.05107(17) Uani 1 1 d . . .
Cl1 Cl 0.10445(6) 0.23369(6) 0.9787(3) 0.0904(8) Uani 1 1 d . . .
Cl2 Cl 0.10850(6) 0.26598(6) 0.7226(3) 0.0950(8) Uani 1 1 d . . .
Cl3 Cl 0.14243(7) 0.29730(6) 0.9643(4) 0.1108(10) Uani 1 1 d . . .
Cl4 Cl 0.21969(9) 0.39098(12) 0.3099(5) 0.1126(16) Uani 0.67 1 d P . .
Cl5 Cl 0.18220(13) 0.41571(11) 0.3403(6) 0.1240(18) Uani 0.67 1 d P . .
Cl6 Cl 0.16129(9) 0.36109(10) 0.1915(4) 0.0929(12) Uani 0.67 1 d P . .
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'
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
_geom_angle_publ_flag
C6 C1 C2 124.4(6) . . ?
C6 C1 N1 117.5(6) . . ?
C2 C1 N1 118.0(6) . . ?
C3 C2 C1 117.2(6) . . ?
C3 C2 C7 120.3(7) . . ?
C1 C2 C7 122.5(7) . . ?
C2 C3 C4 120.8(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.3(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 122.3(7) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 116.1(6) . . ?
C1 C6 C10 123.1(6) . . ?
C5 C6 C10 120.9(6) . . ?
C9 C7 C8 111.3(7) . . ?
C9 C7 C2 111.6(7) . . ?
C8 C7 C2 112.8(7) . . ?
C9 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C2 C7 H7 107.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 112.0(6) . . ?
C11 C10 C12 105.8(6) . . ?
C6 C10 C12 112.6(6) . . ?
C11 C10 H10 108.8 . . ?
C6 C10 H10 108.8 . . ?
C12 C10 H10 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 N1 107.7(5) . . ?
N2 C13 H13 126.1 . . ?
N1 C13 H13 126.1 . . ?
C15 C14 N1 108.2(6) . . ?
C15 C14 H14 125.9 . . ?
N1 C14 H14 125.9 . . ?
C14 C15 N2 106.9(6) . . ?
C14 C15 H15 126.5 . . ?
N2 C15 H15 126.5 . . ?
N3 C16 C17 125.4(6) . . ?
N3 C16 N2 112.0(6) . . ?
C17 C16 N2 122.6(6) . . ?
C18 C17 C16 114.6(6) . . ?
C18 C17 C36 121.3(6) . . ?
C16 C17 C36 124.1(6) . . ?
C17 C18 C19 124.0(6) . . ?
C17 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
C18 C19 C20 114.4(6) . . ?
C18 C19 C37 121.6(6) . . ?
C20 C19 C37 124.0(6) . . ?
N3 C20 C19 125.4(6) . . ?
N3 C20 N4 112.6(5) . . ?
C19 C20 N4 122.0(6) . . ?
N5 C21 N4 108.6(5) . . ?
N5 C21 H21 125.7 . . ?
N4 C21 H21 125.7 . . ?
C23 C22 N4 106.8(6) . . ?
C23 C22 H22 126.6 . . ?
N4 C22 H22 126.6 . . ?
C22 C23 N5 107.7(6) . . ?
C22 C23 H23 126.1 . . ?
N5 C23 H23 126.1 . . ?
C25 C24 C29 124.4(6) . . ?
C25 C24 N5 118.3(6) . . ?
C29 C24 N5 117.2(6) . . ?
C26 C25 C24 117.2(7) . . ?
C26 C25 C30 120.3(7) . . ?
C24 C25 C30 122.5(6) . . ?
C25 C26 C27 120.4(7) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 121.0(7) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 121.8(7) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C28 C29 C24 115.3(7) . . ?
C28 C29 C33 120.9(7) . . ?
C24 C29 C33 123.7(6) . . ?
C25 C30 C31 109.2(7) . . ?
C25 C30 C32 113.5(6) . . ?
C31 C30 C32 110.0(7) . . ?
C25 C30 H30 108.0 . . ?
C31 C30 H30 108.0 . . ?
C32 C30 H30 108.0 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 C35 112.4(6) . . ?
C29 C33 C34 110.4(6) . . ?
C35 C33 C34 112.2(7) . . ?
C29 C33 H33 107.2 . . ?
C35 C33 H33 107.2 . . ?
C34 C33 H33 107.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C17 C36 H36A 109.5 . . ?
C17 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C17 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C19 C37 H37A 109.5 . . ?
C19 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C19 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
Cl3 C38 Cl2 109.1(6) . . ?
Cl3 C38 Cl1 111.6(5) . . ?
Cl2 C38 Cl1 109.9(5) . . ?
Cl3 C38 H38 108.7 . . ?
Cl2 C38 H38 108.7 . . ?
Cl1 C38 H38 108.7 . . ?
Cl4 C39 Cl5 113.1(8) . . ?
Cl4 C39 Cl6 112.6(7) . . ?
Cl5 C39 Cl6 111.8(7) . . ?
Cl4 C39 H39 106.2 . . ?
Cl5 C39 H39 106.2 . . ?
Cl6 C39 H39 106.2 . . ?
C13 N1 C14 108.7(6) . . ?
C13 N1 C1 125.1(5) . . ?
C14 N1 C1 126.1(5) . . ?
C13 N2 C15 108.5(5) . . ?
C13 N2 C16 125.5(5) . . ?
C15 N2 C16 125.9(5) . . ?
C20 N3 C16 116.2(5) . . ?
C21 N4 C22 108.5(5) . . ?
C21 N4 C20 125.6(5) . . ?
C22 N4 C20 125.8(5) . . ?
C21 N5 C23 108.4(5) . . ?
C21 N5 C24 125.0(5) . . ?
C23 N5 C24 126.6(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.387(9) . ?
C1 C2 1.397(10) . ?
C1 N1 1.448(8) . ?
C2 C3 1.389(10) . ?
C2 C7 1.526(10) . ?
C3 C4 1.400(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(9) . ?
C5 H5 0.9500 . ?
C6 C10 1.520(9) . ?
C7 C9 1.487(11) . ?
C7 C8 1.518(11) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.505(10) . ?
C10 C12 1.551(11) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.333(8) . ?
C13 N1 1.341(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.324(9) . ?
C14 N1 1.371(8) . ?
C14 H14 0.9500 . ?
C15 N2 1.396(8) . ?
C15 H15 0.9500 . ?
C16 N3 1.335(8) . ?
C16 C17 1.399(9) . ?
C16 N2 1.439(8) . ?
C17 C18 1.368(9) . ?
C17 C36 1.507(9) . ?
C18 C19 1.381(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.406(9) . ?
C19 C37 1.496(9) . ?
C20 N3 1.321(8) . ?
C20 N4 1.433(8) . ?
C21 N5 1.331(8) . ?
C21 N4 1.335(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.343(9) . ?
C22 N4 1.388(8) . ?
C22 H22 0.9500 . ?
C23 N5 1.382(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(9) . ?
C24 C29 1.403(10) . ?
C24 N5 1.449(8) . ?
C25 C26 1.385(9) . ?
C25 C30 1.511(10) . ?
C26 C27 1.390(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.359(11) . ?
C27 H27 0.9500 . ?
C28 C29 1.403(10) . ?
C28 H28 0.9500 . ?
C29 C33 1.492(10) . ?
C30 C31 1.513(11) . ?
C30 C32 1.525(11) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C35 1.502(11) . ?
C33 C34 1.511(11) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 Cl3 1.737(9) . ?
C38 Cl2 1.762(11) . ?
C38 Cl1 1.774(10) . ?
C38 H38 1.0000 . ?
C39 Cl4 1.705(12) . ?
C39 Cl5 1.714(13) . ?
C39 Cl6 1.747(12) . ?
C39 H39 1.0000 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(10) . . . . ?
N1 C1 C2 C3 -178.8(6) . . . . ?
C6 C1 C2 C7 178.7(6) . . . . ?
N1 C1 C2 C7 0.4(10) . . . . ?
C1 C2 C3 C4 2.0(10) . . . . ?
C7 C2 C3 C4 -177.2(6) . . . . ?
C2 C3 C4 C5 -2.4(10) . . . . ?
C3 C4 C5 C6 1.3(10) . . . . ?
C2 C1 C6 C5 -0.5(10) . . . . ?
N1 C1 C6 C5 177.7(5) . . . . ?
C2 C1 C6 C10 179.2(6) . . . . ?
N1 C1 C6 C10 -2.5(9) . . . . ?
C4 C5 C6 C1 0.2(9) . . . . ?
C4 C5 C6 C10 -179.6(6) . . . . ?
C3 C2 C7 C9 68.9(9) . . . . ?
C1 C2 C7 C9 -110.3(8) . . . . ?
C3 C2 C7 C8 -57.1(10) . . . . ?
C1 C2 C7 C8 123.7(8) . . . . ?
C1 C6 C10 C11 101.6(8) . . . . ?
C5 C6 C10 C11 -78.6(8) . . . . ?
C1 C6 C10 C12 -139.2(7) . . . . ?
C5 C6 C10 C12 40.5(9) . . . . ?
N1 C14 C15 N2 -1.0(8) . . . . ?
N3 C16 C17 C18 -1.9(9) . . . . ?
N2 C16 C17 C18 178.3(5) . . . . ?
N3 C16 C17 C36 177.7(6) . . . . ?
N2 C16 C17 C36 -2.2(10) . . . . ?
C16 C17 C18 C19 1.2(9) . . . . ?
C36 C17 C18 C19 -178.4(6) . . . . ?
C17 C18 C19 C20 -0.8(9) . . . . ?
C17 C18 C19 C37 176.9(6) . . . . ?
C18 C19 C20 N3 1.2(9) . . . . ?
C37 C19 C20 N3 -176.5(6) . . . . ?
C18 C19 C20 N4 -179.4(5) . . . . ?
C37 C19 C20 N4 2.9(9) . . . . ?
N4 C22 C23 N5 0.3(8) . . . . ?
C29 C24 C25 C26 -0.6(10) . . . . ?
N5 C24 C25 C26 -178.0(6) . . . . ?
C29 C24 C25 C30 179.7(6) . . . . ?
N5 C24 C25 C30 2.4(9) . . . . ?
C24 C25 C26 C27 -0.9(10) . . . . ?
C30 C25 C26 C27 178.7(6) . . . . ?
C25 C26 C27 C28 2.0(10) . . . . ?
C26 C27 C28 C29 -1.4(10) . . . . ?
C27 C28 C29 C24 -0.1(9) . . . . ?
C27 C28 C29 C33 177.6(6) . . . . ?
C25 C24 C29 C28 1.1(9) . . . . ?
N5 C24 C29 C28 178.5(5) . . . . ?
C25 C24 C29 C33 -176.5(6) . . . . ?
N5 C24 C29 C33 0.9(9) . . . . ?
C26 C25 C30 C31 -74.5(8) . . . . ?
C24 C25 C30 C31 105.1(8) . . . . ?
C26 C25 C30 C32 48.6(9) . . . . ?
C24 C25 C30 C32 -131.8(7) . . . . ?
C28 C29 C33 C35 58.9(9) . . . . ?
C24 C29 C33 C35 -123.6(8) . . . . ?
C28 C29 C33 C34 -67.2(9) . . . . ?
C24 C29 C33 C34 110.2(8) . . . . ?
N2 C13 N1 C14 0.0(8) . . . . ?
N2 C13 N1 C1 -176.6(6) . . . . ?
C15 C14 N1 C13 0.6(8) . . . . ?
C15 C14 N1 C1 177.3(7) . . . . ?
C6 C1 N1 C13 90.7(8) . . . . ?
C2 C1 N1 C13 -91.0(8) . . . . ?
C6 C1 N1 C14 -85.4(8) . . . . ?
C2 C1 N1 C14 93.0(8) . . . . ?
N1 C13 N2 C15 -0.7(7) . . . . ?
N1 C13 N2 C16 -176.2(6) . . . . ?
C14 C15 N2 C13 1.1(8) . . . . ?
C14 C15 N2 C16 176.6(6) . . . . ?
N3 C16 N2 C13 133.5(6) . . . . ?
C17 C16 N2 C13 -46.6(9) . . . . ?
N3 C16 N2 C15 -41.2(8) . . . . ?
C17 C16 N2 C15 138.6(7) . . . . ?
C19 C20 N3 C16 -1.8(9) . . . . ?
N4 C20 N3 C16 178.8(5) . . . . ?
C17 C16 N3 C20 2.2(9) . . . . ?
N2 C16 N3 C20 -178.0(5) . . . . ?
N5 C21 N4 C22 0.8(7) . . . . ?
N5 C21 N4 C20 177.1(6) . . . . ?
C23 C22 N4 C21 -0.7(7) . . . . ?
C23 C22 N4 C20 -176.9(6) . . . . ?
N3 C20 N4 C21 -133.8(6) . . . . ?
C19 C20 N4 C21 46.7(9) . . . . ?
N3 C20 N4 C22 41.8(8) . . . . ?
C19 C20 N4 C22 -137.7(6) . . . . ?
N4 C21 N5 C23 -0.6(7) . . . . ?
N4 C21 N5 C24 -179.4(6) . . . . ?
C22 C23 N5 C21 0.2(8) . . . . ?
C22 C23 N5 C24 178.9(6) . . . . ?
C25 C24 N5 C21 85.5(8) . . . . ?
C29 C24 N5 C21 -92.1(8) . . . . ?
C25 C24 N5 C23 -93.0(8) . . . . ?
C29 C24 N5 C23 89.4(8) . . . . ?
