#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:48:26 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179207 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/39/4313953.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_4313953
loop_
_publ_author_name
'Timothy J. Foley'
'Benjamin S. Harrison'
'Alison S. Knefely'
'Khalil A. Abboud'
'John R. Reynolds'
'Kirk S. Schanze'
'James M. Boncella'
_publ_section_title
;
 Facile Preparation and Photophysics of Near-Infrared Luminescent
 Lanthanide(III) Monoporphyrinate Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5023
_journal_page_last               5032
_journal_paper_doi               10.1021/ic034217g
_journal_volume                  42
_journal_year                    2003
_chemical_formula_moiety         'C53 H38 B N4 Tm, 2(C1 H1 Cl3)'
_chemical_formula_sum            'C55 H40 B Cl6 N10 Tm'
_chemical_formula_weight         1233.41
_chemical_name_systematic
;
   ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 98.808(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4931(8)
_cell_length_b                   14.6041(6)
_cell_length_c                   19.4154(9)
_cell_measurement_temperature    193(2)
_cell_volume                     5181.8(4)
_computing_cell_refinement       'Bruker SMART & SAINT (Bruker 1998)'
_computing_data_collection       'Bruker SMART (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL (Bruker 1998)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            46178
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  0.7940
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, SHELXTL (Bruker 1998)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.162
_refine_diff_density_min         -1.833
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.00093(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     663
_refine_ls_number_reflns         11868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0154P)²+11.9242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                10920
_reflns_number_total             11868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034217gsi20030318_055518_3.cif
_cod_data_source_block           tf25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4313953
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Tm Tm 0.475087(7) 0.738557(8) 0.767705(6) 0.01666(5) Uani 1 1 d . . .
N1 N 0.40919(13) 0.86042(17) 0.81039(13) 0.0199(5) Uani 1 1 d . . .
N2 N 0.35441(13) 0.72225(17) 0.70880(12) 0.0188(5) Uani 1 1 d . . .
N3 N 0.48799(14) 0.73398(17) 0.64912(13) 0.0204(5) Uani 1 1 d . . .
N4 N 0.54263(14) 0.87230(18) 0.75039(13) 0.0200(5) Uani 1 1 d . . .
C1 C 0.43744(16) 0.9402(2) 0.84286(15) 0.0206(6) Uani 1 1 d . . .
C2 C 0.38485(17) 0.9808(2) 0.88103(17) 0.0250(6) Uani 1 1 d . . .
H2A H 0.3917 1.0345 0.9089 0.030 Uiso 1 1 calc R . .
C3 C 0.32395(18) 0.9285(2) 0.86997(17) 0.0257(7) Uani 1 1 d . . .
H3A H 0.2803 0.9378 0.8893 0.031 Uiso 1 1 calc R . .
C4 C 0.33760(16) 0.8563(2) 0.82351(15) 0.0203(6) Uani 1 1 d . . .
C5 C 0.28256(16) 0.8002(2) 0.78893(16) 0.0209(6) Uani 1 1 d . . .
C6 C 0.29023(16) 0.7403(2) 0.73398(15) 0.0208(6) Uani 1 1 d . . .
C7 C 0.23039(17) 0.6911(2) 0.69423(16) 0.0243(6) Uani 1 1 d . . .
H7A H 0.1808 0.6913 0.7017 0.029 Uiso 1 1 calc R . .
C8 C 0.25841(17) 0.6447(2) 0.64437(16) 0.0235(6) Uani 1 1 d . . .
H8A H 0.2322 0.6051 0.6105 0.028 Uiso 1 1 calc R . .
C9 C 0.33500(16) 0.6658(2) 0.65173(15) 0.0198(6) Uani 1 1 d . . .
C10 C 0.37906(17) 0.6424(2) 0.60210(15) 0.0219(6) Uani 1 1 d . . .
C11 C 0.44927(17) 0.6772(2) 0.59965(15) 0.0219(6) Uani 1 1 d . . .
C12 C 0.48985(18) 0.6630(2) 0.54306(17) 0.0282(7) Uani 1 1 d . . .
H12A H 0.4756 0.6259 0.5031 0.034 Uiso 1 1 calc R . .
C13 C 0.55195(18) 0.7124(2) 0.55722(17) 0.0281(7) Uani 1 1 d . . .
H13A H 0.5893 0.7171 0.5289 0.034 Uiso 1 1 calc R . .
C14 C 0.55102(17) 0.7568(2) 0.62357(15) 0.0225(6) Uani 1 1 d . . .
C15 C 0.60592(17) 0.8159(2) 0.65552(16) 0.0220(6) Uani 1 1 d . . .
C16 C 0.60103(16) 0.8710(2) 0.71354(16) 0.0223(6) Uani 1 1 d . . .
C17 C 0.65124(17) 0.9441(2) 0.73695(17) 0.0255(7) Uani 1 1 d . . .
H17A H 0.6971 0.9554 0.7223 0.031 Uiso 1 1 calc R . .
C18 C 0.62049(17) 0.9934(2) 0.78376(17) 0.0256(6) Uani 1 1 d . . .
H18A H 0.6401 1.0472 0.8071 0.031 Uiso 1 1 calc R . .
C19 C 0.55261(17) 0.9495(2) 0.79173(16) 0.0219(6) Uani 1 1 d . . .
C20 C 0.50376(17) 0.9819(2) 0.83438(15) 0.0210(6) Uani 1 1 d . . .
C21 C 0.20635(17) 0.8121(2) 0.80549(17) 0.0253(7) Uani 1 1 d . . .
C22 C 0.1794(2) 0.7572(3) 0.8538(2) 0.0403(9) Uani 1 1 d . . .
H22A H 0.2101 0.7133 0.8799 0.048 Uiso 1 1 calc R . .
C23 C 0.1059(3) 0.7671(3) 0.8638(3) 0.0577(14) Uani 1 1 d . . .
H23A H 0.0867 0.7285 0.8960 0.069 Uiso 1 1 calc R . .
C24 C 0.0619(2) 0.8315(4) 0.8276(3) 0.0573(14) Uani 1 1 d . . .
H24A H 0.0125 0.8377 0.8351 0.069 Uiso 1 1 calc R . .
C25 C 0.0886(2) 0.8873(4) 0.7806(2) 0.0534(13) Uani 1 1 d . . .
H25A H 0.0579 0.9323 0.7557 0.064 Uiso 1 1 calc R . .
C26 C 0.1607(2) 0.8779(3) 0.7694(2) 0.0395(9) Uani 1 1 d . . .
H26A H 0.1791 0.9167 0.7368 0.047 Uiso 1 1 calc R . .
C27 C 0.34463(16) 0.5841(2) 0.54204(15) 0.0221(6) Uani 1 1 d . . .
C28 C 0.34066(19) 0.4897(2) 0.54770(17) 0.0294(7) Uani 1 1 d . . .
H28A H 0.3623 0.4604 0.5895 0.035 Uiso 1 1 calc R . .
C29 C 0.3054(2) 0.4375(3) 0.49279(19) 0.0358(8) Uani 1 1 d . . .
H29A H 0.3027 0.3729 0.4972 0.043 Uiso 1 1 calc R . .
C30 C 0.2744(2) 0.4795(3) 0.43199(19) 0.0368(8) Uani 1 1 d . . .
H30A H 0.2505 0.4438 0.3943 0.044 Uiso 1 1 calc R . .
C31 C 0.2778(2) 0.5733(3) 0.42551(18) 0.0381(9) Uani 1 1 d . . .
H31A H 0.2561 0.6021 0.3835 0.046 Uiso 1 1 calc R . .
C32 C 0.31287(19) 0.6259(2) 0.48033(17) 0.0307(7) Uani 1 1 d . . .
H32A H 0.3152 0.6906 0.4757 0.037 Uiso 1 1 calc R . .
C33 C 0.67174(17) 0.8257(2) 0.61937(16) 0.0229(6) Uani 1 1 d . . .
C34 C 0.73014(19) 0.7666(2) 0.6346(2) 0.0328(7) Uani 1 1 d . . .
H34A H 0.7301 0.7223 0.6704 0.039 Uiso 1 1 calc R . .
C35 C 0.7893(2) 0.7712(3) 0.5979(2) 0.0369(8) Uani 1 1 d . . .
H35A H 0.8293 0.7302 0.6087 0.044 Uiso 1 1 calc R . .
C36 C 0.78950(19) 0.8352(3) 0.54604(19) 0.0350(8) Uani 1 1 d . . .
H36A H 0.8294 0.8380 0.5205 0.042 Uiso 1 1 calc R . .
C37 C 0.7323(2) 0.8950(3) 0.5313(2) 0.0491(11) Uani 1 1 d . . .
H37A H 0.7328 0.9398 0.4958 0.059 Uiso 1 1 calc R . .
C38 C 0.6732(2) 0.8904(3) 0.5681(2) 0.0435(10) Uani 1 1 d . . .
H38A H 0.6337 0.9323 0.5576 0.052 Uiso 1 1 calc R . .
C39 C 0.51831(16) 1.0729(2) 0.86999(16) 0.0225(6) Uani 1 1 d . . .
C40 C 0.5477(2) 1.0795(2) 0.93979(18) 0.0327(8) Uani 1 1 d . . .
H40A H 0.5647 1.0258 0.9649 0.039 Uiso 1 1 calc R . .
C41 C 0.5528(2) 1.1638(3) 0.9737(2) 0.0367(8) Uani 1 1 d . . .
H41A H 0.5730 1.1673 1.0217 0.044 Uiso 1 1 calc R . .
C42 C 0.5289(2) 1.2419(2) 0.9381(2) 0.0359(8) Uani 1 1 d . . .
H42A H 0.5313 1.2991 0.9616 0.043 Uiso 1 1 calc R . .
C43 C 0.5013(2) 1.2371(3) 0.8680(2) 0.0418(9) Uani 1 1 d . . .
H43A H 0.4860 1.2913 0.8429 0.050 Uiso 1 1 calc R . .
C44 C 0.4958(2) 1.1531(2) 0.8342(2) 0.0353(8) Uani 1 1 d . . .
H44A H 0.4765 1.1502 0.7860 0.042 Uiso 1 1 calc R . .
B B 0.5563(2) 0.5623(3) 0.88674(19) 0.0256(7) Uani 1 1 d . . .
HB H 0.579(2) 0.513(3) 0.9221(19) 0.027(9) Uiso 1 1 d . . .
N5 N 0.42724(15) 0.61788(19) 0.84030(14) 0.0256(6) Uani 1 1 d . . .
N6 N 0.47252(15) 0.55888(18) 0.88138(14) 0.0243(5) Uani 1 1 d . . .
N7 N 0.55355(15) 0.60063(19) 0.75870(14) 0.0266(6) Uani 1 1 d . . .
N8 N 0.57724(15) 0.54545(19) 0.81462(14) 0.0269(6) Uani 1 1 d . . .
N9 N 0.56239(15) 0.73615(19) 0.87951(14) 0.0276(6) Uani 1 1 d . . .
N10 N 0.58385(15) 0.6565(2) 0.91362(14) 0.0261(6) Uani 1 1 d . . .
C45 C 0.35934(19) 0.5923(3) 0.84777(19) 0.0320(8) Uani 1 1 d . . .
H45A H 0.3162 0.6212 0.8250 0.038 Uiso 1 1 calc R . .
C46 C 0.3598(2) 0.5183(3) 0.89292(19) 0.0345(8) Uani 1 1 d . . .
H46A H 0.3190 0.4878 0.9068 0.041 Uiso 1 1 calc R . .
C47 C 0.43271(19) 0.4995(2) 0.91276(18) 0.0299(7) Uani 1 1 d . . .
H47A H 0.4519 0.4521 0.9438 0.036 Uiso 1 1 calc R . .
C48 C 0.5807(2) 0.5638(2) 0.70491(19) 0.0329(8) Uani 1 1 d . . .
H48A H 0.5728 0.5876 0.6588 0.040 Uiso 1 1 calc R . .
C49 C 0.6221(2) 0.4860(3) 0.7253(2) 0.0418(9) Uani 1 1 d . . .
H49A H 0.6472 0.4477 0.6972 0.050 Uiso 1 1 calc R . .
C50 C 0.6183(2) 0.4771(3) 0.7956(2) 0.0373(8) Uani 1 1 d . . .
H50A H 0.6410 0.4303 0.8253 0.045 Uiso 1 1 calc R . .
C51 C 0.5978(2) 0.8024(3) 0.91848(19) 0.0357(8) Uani 1 1 d . . .
H51A H 0.5939 0.8657 0.9073 0.043 Uiso 1 1 calc R . .
C52 C 0.6411(2) 0.7676(3) 0.97722(19) 0.0400(9) Uani 1 1 d . . .
H52A H 0.6711 0.8006 1.0129 0.048 Uiso 1 1 calc R . .
C53 C 0.63071(19) 0.6748(3) 0.97206(18) 0.0330(8) Uani 1 1 d . . .
H53A H 0.6530 0.6306 1.0045 0.040 Uiso 1 1 calc R . .
C54 C 0.3602(3) 0.8481(3) 0.3503(3) 0.0596(13) Uani 1 1 d . . .
H54A H 0.3728 0.9096 0.3328 0.072 Uiso 1 1 calc R . .
Cl1 Cl 0.27030(9) 0.85194(15) 0.36607(11) 0.1049(7) Uani 1 1 d . . .
Cl2 Cl 0.42064(9) 0.82511(13) 0.42656(7) 0.0804(4) Uani 1 1 d . . .
Cl3 Cl 0.37058(10) 0.76684(12) 0.28629(9) 0.0837(5) Uani 1 1 d . . .
C55 C 0.3838(2) 0.9415(3) 0.6378(2) 0.0462(10) Uani 1 1 d . . .
H55A H 0.4089 0.8948 0.6709 0.055 Uiso 1 1 calc R . .
Cl4 Cl 0.45048(8) 0.99836(13) 0.59876(9) 0.0850(5) Uani 1 1 d . . .
Cl5 Cl 0.32107(7) 0.88403(8) 0.57502(6) 0.0591(3) Uani 1 1 d . . .
Cl6 Cl 0.33767(7) 1.01799(8) 0.68545(6) 0.0566(3) 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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tm Tm -0.3139 5.2483 '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
N3 Tm N2 75.68(8) . . ?
N3 Tm N4 75.51(9) . . ?
N2 Tm N4 119.64(9) . . ?
N3 Tm N1 119.80(9) . . ?
N2 Tm N1 75.35(8) . . ?
N4 Tm N1 75.04(9) . . ?
N3 Tm N9 134.51(9) . . ?
N2 Tm N9 148.99(9) . . ?
N4 Tm N9 81.40(9) . . ?
N1 Tm N9 90.30(9) . . ?
N3 Tm N5 129.00(9) . . ?
N2 Tm N5 79.17(8) . . ?
N4 Tm N5 154.18(9) . . ?
N1 Tm N5 94.97(9) . . ?
N9 Tm N5 74.80(9) . . ?
N3 Tm N7 76.24(9) . . ?
N2 Tm N7 113.59(9) . . ?
N4 Tm N7 109.23(9) . . ?
N1 Tm N7 163.78(8) . . ?
N9 Tm N7 75.24(9) . . ?
N5 Tm N7 74.42(9) . . ?
C4 N1 C1 104.8(2) . . ?
C4 N1 Tm 125.9(2) . . ?
C1 N1 Tm 127.55(19) . . ?
C6 N2 C9 105.5(2) . . ?
C6 N2 Tm 127.71(19) . . ?
C9 N2 Tm 123.97(19) . . ?
C14 N3 C11 105.8(2) . . ?
C14 N3 Tm 124.39(19) . . ?
C11 N3 Tm 125.29(19) . . ?
C19 N4 C16 105.4(3) . . ?
C19 N4 Tm 128.13(19) . . ?
C16 N4 Tm 122.2(2) . . ?
N1 C1 C20 125.9(3) . . ?
N1 C1 C2 110.0(3) . . ?
C20 C1 C2 123.7(3) . . ?
C3 C2 C1 107.4(3) . . ?
C3 C2 H2A 126.3 . . ?
C1 C2 H2A 126.3 . . ?
C2 C3 C4 107.0(3) . . ?
C2 C3 H3A 126.5 . . ?
C4 C3 H3A 126.5 . . ?
N1 C4 C5 125.6(3) . . ?
N1 C4 C3 110.4(3) . . ?
C5 C4 C3 123.3(3) . . ?
C4 C5 C6 125.5(3) . . ?
C4 C5 C21 117.9(3) . . ?
C6 C5 C21 116.2(3) . . ?
N2 C6 C5 125.6(3) . . ?
N2 C6 C7 110.3(3) . . ?
C5 C6 C7 124.0(3) . . ?
C8 C7 C6 106.7(3) . . ?
C8 C7 H7A 126.6 . . ?
C6 C7 H7A 126.6 . . ?
C7 C8 C9 107.6(3) . . ?
C7 C8 H8A 126.2 . . ?
C9 C8 H8A 126.2 . . ?
N2 C9 C10 126.3(3) . . ?
N2 C9 C8 109.8(3) . . ?
C10 C9 C8 123.3(3) . . ?
C9 C10 C11 125.2(3) . . ?
C9 C10 C27 116.8(3) . . ?
C11 C10 C27 117.6(3) . . ?
N3 C11 C10 125.3(3) . . ?
N3 C11 C12 110.0(3) . . ?
C10 C11 C12 124.7(3) . . ?
C13 C12 C11 107.2(3) . . ?
C13 C12 H12A 126.4 . . ?
C11 C12 H12A 126.4 . . ?
C12 C13 C14 107.2(3) . . ?
C12 C13 H13A 126.4 . . ?
C14 C13 H13A 126.4 . . ?
N3 C14 C15 125.8(3) . . ?
N3 C14 C13 109.8(3) . . ?
C15 C14 C13 124.3(3) . . ?
C16 C15 C14 125.4(3) . . ?
C16 C15 C33 118.6(3) . . ?
C14 C15 C33 115.8(3) . . ?
N4 C16 C15 125.2(3) . . ?
N4 C16 C17 110.1(3) . . ?
C15 C16 C17 124.2(3) . . ?
C18 C17 C16 106.8(3) . . ?
C18 C17 H17A 126.6 . . ?
C16 C17 H17A 126.6 . . ?
C17 C18 C19 107.4(3) . . ?
C17 C18 H18A 126.3 . . ?
C19 C18 H18A 126.3 . . ?
N4 C19 C20 125.4(3) . . ?
N4 C19 C18 110.0(3) . . ?
C20 C19 C18 124.5(3) . . ?
C19 C20 C1 125.4(3) . . ?
C19 C20 C39 119.0(3) . . ?
C1 C20 C39 115.3(3) . . ?
C22 C21 C26 119.1(3) . . ?
C22 C21 C5 121.7(3) . . ?
C26 C21 C5 119.2(3) . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24A 119.9 . . ?
C25 C24 H24A 119.9 . . ?
C24 C25 C26 119.8(4) . . ?
C24 C25 H25A 120.1 . . ?
C26 C25 H25A 120.1 . . ?
C25 C26 C21 120.7(4) . . ?
C25 C26 H26A 119.7 . . ?
C21 C26 H26A 119.7 . . ?
C28 C27 C32 119.0(3) . . ?
C28 C27 C10 121.5(3) . . ?
C32 C27 C10 119.4(3) . . ?
C27 C28 C29 120.6(3) . . ?
C27 C28 H28A 119.7 . . ?
C29 C28 H28A 119.7 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29A 120.0 . . ?
C28 C29 H29A 120.0 . . ?
C29 C30 C31 120.2(3) . . ?
C29 C30 H30A 119.9 . . ?
C31 C30 H30A 119.9 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31A 119.9 . . ?
C32 C31 H31A 119.9 . . ?
C31 C32 C27 120.1(3) . . ?
C31 C32 H32A 119.9 . . ?
C27 C32 H32A 119.9 . . ?
C38 C33 C34 118.9(3) . . ?
C38 C33 C15 120.8(3) . . ?
C34 C33 C15 120.3(3) . . ?
C33 C34 C35 120.7(3) . . ?
C33 C34 H34A 119.7 . . ?
C35 C34 H34A 119.7 . . ?
C36 C35 C34 119.8(3) . . ?
C36 C35 H35A 120.1 . . ?
C34 C35 H35A 120.1 . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 H36A 120.0 . . ?
C35 C36 H36A 120.0 . . ?
C36 C37 C38 120.2(4) . . ?
C36 C37 H37A 119.9 . . ?
C38 C37 H37A 119.9 . . ?
C33 C38 C37 120.5(4) . . ?
C33 C38 H38A 119.7 . . ?
C37 C38 H38A 119.7 . . ?
C40 C39 C44 118.2(3) . . ?
C40 C39 C20 121.8(3) . . ?
C44 C39 C20 119.7(3) . . ?
C39 C40 C41 120.8(3) . . ?
C39 C40 H40A 119.6 . . ?
C41 C40 H40A 119.6 . . ?
C42 C41 C40 120.2(3) . . ?
C42 C41 H41A 119.9 . . ?
C40 C41 H41A 119.9 . . ?
C41 C42 C43 119.8(3) . . ?
C41 C42 H42A 120.1 . . ?
C43 C42 H42A 120.1 . . ?
C42 C43 C44 120.0(4) . . ?
C42 C43 H43A 120.0 . . ?
C44 C43 H43A 120.0 . . ?
C43 C44 C39 120.9(3) . . ?
C43 C44 H44A 119.6 . . ?
C39 C44 H44A 119.6 . . ?
N8 B N10 109.8(3) . . ?
N8 B N6 109.1(3) . . ?
N10 B N6 109.4(3) . . ?
N8 B HB 111(2) . . ?
N10 B HB 108(2) . . ?
N6 B HB 109(2) . . ?
C45 N5 N6 105.1(3) . . ?
C45 N5 Tm 132.5(2) . . ?
N6 N5 Tm 122.27(19) . . ?
C47 N6 N5 110.0(3) . . ?
C47 N6 B 127.4(3) . . ?
N5 N6 B 122.6(3) . . ?
C48 N7 N8 105.6(3) . . ?
C48 N7 Tm 131.9(2) . . ?
N8 N7 Tm 122.4(2) . . ?
C50 N8 N7 110.2(3) . . ?
C50 N8 B 127.3(3) . . ?
N7 N8 B 122.4(3) . . ?
C51 N9 N10 105.1(3) . . ?
C51 N9 Tm 132.6(2) . . ?
N10 N9 Tm 122.3(2) . . ?
C53 N10 N9 110.0(3) . . ?
C53 N10 B 127.1(3) . . ?
N9 N10 B 122.9(3) . . ?
N5 C45 C46 111.7(3) . . ?
N5 C45 H45A 124.1 . . ?
C46 C45 H45A 124.1 . . ?
C47 C46 C45 104.1(3) . . ?
C47 C46 H46A 128.0 . . ?
C45 C46 H46A 128.0 . . ?
N6 C47 C46 109.1(3) . . ?
N6 C47 H47A 125.4 . . ?
C46 C47 H47A 125.4 . . ?
N7 C48 C49 111.2(3) . . ?
N7 C48 H48A 124.4 . . ?
C49 C48 H48A 124.4 . . ?
C50 C49 C48 104.4(3) . . ?
C50 C49 H49A 127.8 . . ?
C48 C49 H49A 127.8 . . ?
N8 C50 C49 108.6(3) . . ?
N8 C50 H50A 125.7 . . ?
C49 C50 H50A 125.7 . . ?
N9 C51 C52 111.8(3) . . ?
N9 C51 H51A 124.1 . . ?
C52 C51 H51A 124.1 . . ?
C53 C52 C51 104.2(3) . . ?
C53 C52 H52A 127.9 . . ?
C51 C52 H52A 127.9 . . ?
N10 C53 C52 108.8(3) . . ?
N10 C53 H53A 125.6 . . ?
C52 C53 H53A 125.6 . . ?
Cl1 C54 Cl2 111.3(3) . . ?
Cl1 C54 Cl3 111.0(3) . . ?
Cl2 C54 Cl3 110.3(3) . . ?
Cl1 C54 H54A 108.1 . . ?
Cl2 C54 H54A 108.1 . . ?
Cl3 C54 H54A 108.1 . . ?
Cl6 C55 Cl4 111.0(3) . . ?
Cl6 C55 Cl5 110.3(2) . . ?
Cl4 C55 Cl5 111.0(3) . . ?
Cl6 C55 H55A 108.2 . . ?
Cl4 C55 H55A 108.2 . . ?
Cl5 C55 H55A 108.2 . . ?
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
Tm N3 2.352(2) . ?
Tm N2 2.359(2) . ?
Tm N4 2.370(3) . ?
Tm N1 2.377(3) . ?
Tm N9 2.499(3) . ?
Tm N5 2.502(3) . ?
Tm N7 2.504(3) . ?
N1 C4 1.387(4) . ?
N1 C1 1.388(4) . ?
N2 C6 1.377(4) . ?
N2 C9 1.383(4) . ?
N3 C14 1.376(4) . ?
N3 C11 1.383(4) . ?
N4 C19 1.380(4) . ?
N4 C16 1.384(4) . ?
C1 C20 1.401(4) . ?
C1 C2 1.438(4) . ?
C2 C3 1.350(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.435(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.397(4) . ?
C5 C6 1.403(4) . ?
C5 C21 1.503(4) . ?
C6 C7 1.440(4) . ?
C7 C8 1.349(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.435(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.396(4) . ?
C10 C11 1.402(4) . ?
C10 C27 1.504(4) . ?
C11 C12 1.437(4) . ?
C12 C13 1.348(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.445(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.403(4) . ?
C15 C16 1.399(4) . ?
C15 C33 1.502(4) . ?
C16 C17 1.441(4) . ?
C17 C18 1.352(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.439(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.398(4) . ?
C20 C39 1.503(4) . ?
C21 C22 1.383(5) . ?
C21 C26 1.396(5) . ?
C22 C23 1.410(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.365(8) . ?
C23 H23A 0.9500 . ?
C24 C25 1.373(7) . ?
C24 H24A 0.9500 . ?
C25 C26 1.390(5) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 C28 1.385(5) . ?
C27 C32 1.392(4) . ?
C28 C29 1.390(5) . ?
C28 H28A 0.9500 . ?
C29 C30 1.375(5) . ?
C29 H29A 0.9500 . ?
C30 C31 1.377(6) . ?
C30 H30A 0.9500 . ?
C31 C32 1.391(5) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
C33 C38 1.376(5) . ?
C33 C34 1.379(5) . ?
C34 C35 1.395(5) . ?
C34 H34A 0.9500 . ?
C35 C36 1.374(5) . ?
C35 H35A 0.9500 . ?
C36 C37 1.368(6) . ?
C36 H36A 0.9500 . ?
C37 C38 1.395(5) . ?
C37 H37A 0.9500 . ?
C38 H38A 0.9500 . ?
C39 C40 1.384(5) . ?
C39 C44 1.393(5) . ?
C40 C41 1.393(5) . ?
C40 H40A 0.9500 . ?
C41 C42 1.371(5) . ?
C41 H41A 0.9500 . ?
C42 C43 1.380(6) . ?
C42 H42A 0.9500 . ?
C43 C44 1.388(5) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?
B N8 1.529(5) . ?
B N10 1.531(5) . ?
B N6 1.538(5) . ?
B HB 1.04(4) . ?
N5 C45 1.339(4) . ?
N5 N6 1.369(3) . ?
N6 C47 1.342(4) . ?
N7 C48 1.339(4) . ?
N7 N8 1.369(4) . ?
N8 C50 1.340(4) . ?
N9 C51 1.337(4) . ?
N9 N10 1.367(4) . ?
N10 C53 1.345(4) . ?
C45 C46 1.391(5) . ?
C45 H45A 0.9500 . ?
C46 C47 1.372(5) . ?
C46 H46A 0.9500 . ?
C47 H47A 0.9500 . ?
C48 C49 1.392(5) . ?
C48 H48A 0.9500 . ?
C49 C50 1.383(5) . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?
C51 C52 1.385(5) . ?
C51 H51A 0.9500 . ?
C52 C53 1.371(6) . ?
C52 H52A 0.9500 . ?
C53 H53A 0.9500 . ?
C54 Cl1 1.737(5) . ?
C54 Cl2 1.745(5) . ?
C54 Cl3 1.751(6) . ?
C54 H54A 1.0000 . ?
C55 Cl6 1.752(5) . ?
C55 Cl4 1.754(5) . ?
C55 Cl5 1.762(5) . ?
C55 H55A 1.0000 . ?
