#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:56:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180161 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/57/7105754.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_7105754
loop_
_publ_author_name
'Soji Shimizu'
'Shota Nakano'
'Takahisa Hosoya'
'Nagao Kobayashi'
_publ_section_title
;
 Pyrene-Fused Subphthalocyanine
;
_journal_name_full               Chem.Commun.
_journal_page_first              316
_journal_paper_doi               10.1039/c0cc01877e
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C50 H27 B F8 N8 O, 2(C H Cl3)'
_chemical_formula_sum            'C52 H29 B Cl6 F8 N8 O'
_chemical_formula_weight         1157.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 99.940(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.946(4)
_cell_length_b                   24.128(4)
_cell_length_c                   19.003(3)
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.19
_cell_measurement_theta_min      2.36
_cell_volume                     10363(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;
Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)
;
_computing_publication_material
;
Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0858
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24288
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 1997)
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       prism
_exptl_crystal_F_000             4672
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_platon_squeeze_details
;
;
_refine_diff_density_max         0.639
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         9133
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1729
_refine_ls_R_factor_gt           0.0990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1912P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2815
_refine_ls_wR_factor_ref         0.3166
_reflns_number_gt                4596
_reflns_number_total             9133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC01877E.TXT
_cod_data_source_block           test_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7105754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 N 0.3014(2) 0.41551(19) -0.0283(2) 0.0367(12) Uani 1 1 d . . .
C1 C 0.3410(3) 0.3784(2) 0.0076(3) 0.0358(14) Uani 1 1 d . . .
C2 C 0.3046(3) 0.3357(2) 0.0334(3) 0.0383(15) Uani 1 1 d . . .
C3 C 0.3190(3) 0.2867(2) 0.0688(3) 0.0377(14) Uani 1 1 d . . .
F1 F 0.37425(16) 0.26673(12) 0.07981(17) 0.0451(9) Uani 1 1 d . . .
C4 C 0.2749(3) 0.2570(2) 0.0938(3) 0.0472(17) Uani 1 1 d . . .
F2 F 0.28746(17) 0.20925(13) 0.12748(18) 0.0549(10) Uani 1 1 d . . .
C5 C 0.2163(3) 0.2772(2) 0.0799(3) 0.0470(17) Uani 1 1 d . . .
F3 F 0.17511(17) 0.24519(14) 0.1038(2) 0.0595(11) Uani 1 1 d . . .
C6 C 0.2021(3) 0.3241(2) 0.0451(3) 0.0438(16) Uani 1 1 d . . .
F4 F 0.14525(17) 0.34175(14) 0.0330(2) 0.0551(10) Uani 1 1 d . . .
C7 C 0.2453(3) 0.3552(2) 0.0199(3) 0.0410(15) Uani 1 1 d . . .
C8 C 0.2452(3) 0.4085(2) -0.0158(3) 0.0389(14) Uani 1 1 d . . .
N2 N 0.2057(2) 0.44935(19) -0.0209(2) 0.0372(12) Uani 1 1 d . . .
N3 N 0.2821(2) 0.51092(18) -0.0447(2) 0.0351(11) Uani 1 1 d . . .
C9 C 0.2265(3) 0.5003(2) -0.0309(3) 0.0373(14) Uani 1 1 d . . .
C10 C 0.2030(3) 0.5543(2) -0.0132(3) 0.0383(14) Uani 1 1 d . . .
C11 C 0.1496(3) 0.5702(2) 0.0046(3) 0.0473(16) Uani 1 1 d . . .
F5 F 0.10475(16) 0.53388(14) 0.0045(2) 0.0569(10) Uani 1 1 d . . .
C12 C 0.1417(3) 0.6243(3) 0.0215(4) 0.0545(19) Uani 1 1 d . . .
F6 F 0.0903(2) 0.64095(15) 0.0390(3) 0.0779(13) Uani 1 1 d . . .
C13 C 0.1873(3) 0.6631(2) 0.0241(4) 0.0540(18) Uani 1 1 d . . .
F7 F 0.1775(2) 0.71436(14) 0.0421(2) 0.0710(12) Uani 1 1 d . . .
C14 C 0.2412(3) 0.6475(2) 0.0075(3) 0.0475(16) Uani 1 1 d . . .
F8 F 0.28339(16) 0.68559(12) 0.00963(18) 0.0499(9) Uani 1 1 d . . .
C15 C 0.2493(3) 0.5931(2) -0.0110(3) 0.0372(14) Uani 1 1 d . . .
C16 C 0.3014(3) 0.5630(2) -0.0243(3) 0.0350(13) Uani 1 1 d . . .
N4 N 0.3584(2) 0.57529(18) -0.0033(2) 0.0367(12) Uani 1 1 d . . .
N5 N 0.3814(2) 0.48030(18) -0.0180(2) 0.0327(11) Uani 1 1 d . . .
C17 C 0.3961(3) 0.5322(2) 0.0059(3) 0.0369(14) Uani 1 1 d . . .
C18 C 0.4507(3) 0.5280(2) 0.0567(3) 0.0339(13) Uani 1 1 d . . .
C19 C 0.4853(3) 0.5689(2) 0.1003(3) 0.0358(14) Uani 1 1 d . . .
C20 C 0.4775(3) 0.6262(2) 0.0882(3) 0.0376(14) Uani 1 1 d . . .
H1 H 0.4481 0.6384 0.0499 0.045 Uiso 1 1 calc R . .
C21 C 0.5118(3) 0.6657(2) 0.1311(3) 0.0373(14) Uani 1 1 d . . .
C22 C 0.5527(3) 0.6465(3) 0.1884(3) 0.0415(15) Uani 1 1 d . . .
H2 H 0.5756 0.6727 0.2186 0.050 Uiso 1 1 calc R . .
C23 C 0.5615(3) 0.5898(2) 0.2035(3) 0.0376(14) Uani 1 1 d . . .
C24 C 0.6033(3) 0.5702(2) 0.2630(3) 0.0371(14) Uani 1 1 d . . .
C25 C 0.6134(3) 0.5146(3) 0.2741(3) 0.0404(15) Uani 1 1 d . . .
C26 C 0.5835(3) 0.4733(2) 0.2254(3) 0.0381(14) Uani 1 1 d . . .
C27 C 0.5971(3) 0.4165(3) 0.2322(3) 0.0453(16) Uani 1 1 d . . .
H3 H 0.6257 0.4044 0.2714 0.054 Uiso 1 1 calc R . .
C28 C 0.5701(3) 0.3781(2) 0.1838(3) 0.0412(15) Uani 1 1 d . . .
C29 C 0.5255(3) 0.3963(2) 0.1298(3) 0.0390(15) Uani 1 1 d . . .
H4 H 0.5052 0.3698 0.0977 0.047 Uiso 1 1 calc R . .
C30 C 0.5096(3) 0.4513(2) 0.1212(3) 0.0364(14) Uani 1 1 d . . .
C31 C 0.4631(3) 0.4712(2) 0.0666(3) 0.0373(14) Uani 1 1 d . . .
C32 C 0.5281(3) 0.5500(2) 0.1574(3) 0.0352(14) Uani 1 1 d . . .
C33 C 0.5402(2) 0.4925(2) 0.1685(3) 0.0327(13) Uani 1 1 d . . .
C34 C 0.4158(3) 0.4421(2) 0.0218(3) 0.0359(14) Uani 1 1 d . . .
N6 N 0.3979(2) 0.38907(18) 0.0292(2) 0.0354(11) Uani 1 1 d . . .
C35 C 0.5032(3) 0.7272(2) 0.1120(3) 0.0440(15) Uani 1 1 d . . .
C36 C 0.4385(3) 0.7434(2) 0.1130(4) 0.0555(18) Uani 1 1 d . . .
H5 H 0.4122 0.7215 0.0773 0.083 Uiso 1 1 calc R . .
H6 H 0.4329 0.7829 0.1018 0.083 Uiso 1 1 calc R . .
H7 H 0.4290 0.7361 0.1605 0.083 Uiso 1 1 calc R . .
C37 C 0.5191(4) 0.7359(3) 0.0371(3) 0.061(2) Uani 1 1 d . . .
H8 H 0.5606 0.7259 0.0381 0.092 Uiso 1 1 calc R . .
H9 H 0.5131 0.7749 0.0233 0.092 Uiso 1 1 calc R . .
H10 H 0.4937 0.7124 0.0025 0.092 Uiso 1 1 calc R . .
C38 C 0.5437(3) 0.7650(2) 0.1645(3) 0.0495(17) Uani 1 1 d . . .
H11 H 0.5328 0.7620 0.2120 0.074 Uiso 1 1 calc R . .
H12 H 0.5391 0.8034 0.1480 0.074 Uiso 1 1 calc R . .
H13 H 0.5850 0.7534 0.1670 0.074 Uiso 1 1 calc R . .
N7 N 0.6655(3) 0.6413(2) 0.3460(3) 0.0557(15) Uani 1 1 d . . .
C39 C 0.6381(3) 0.6093(3) 0.3093(3) 0.0433(15) Uani 1 1 d . . .
C40 C 0.6565(3) 0.4954(2) 0.3348(3) 0.0417(15) Uani 1 1 d . . .
N8 N 0.6883(3) 0.4791(2) 0.3829(3) 0.0510(14) Uani 1 1 d . . .
C41 C 0.5910(4) 0.3173(3) 0.1859(3) 0.062(2) Uani 1 1 d . . .
C42 C 0.6343(5) 0.3126(3) 0.1342(4) 0.104(4) Uani 1 1 d . . .
H14 H 0.6684 0.3367 0.1502 0.157 Uiso 1 1 calc R . .
H15 H 0.6148 0.3240 0.0864 0.157 Uiso 1 1 calc R . .
H16 H 0.6477 0.2741 0.1327 0.157 Uiso 1 1 calc R . .
C43 C 0.6224(4) 0.3006(3) 0.2603(4) 0.076(2) Uani 1 1 d . . .
H17 H 0.6600 0.3206 0.2718 0.114 Uiso 1 1 calc R . .
H18 H 0.6300 0.2606 0.2614 0.114 Uiso 1 1 calc R . .
H19 H 0.5973 0.3099 0.2955 0.114 Uiso 1 1 calc R . .
C44 C 0.5390(5) 0.2772(3) 0.1645(5) 0.099(3) Uani 1 1 d . . .
H20 H 0.5529 0.2390 0.1732 0.148 Uiso 1 1 calc R . .
H21 H 0.5227 0.2819 0.1137 0.148 Uiso 1 1 calc R . .
H22 H 0.5082 0.2850 0.1930 0.148 Uiso 1 1 calc R . .
B1 B 0.3229(3) 0.4668(3) -0.0632(4) 0.0371(16) Uani 1 1 d . . .
O1 O 0.32737(17) 0.46112(16) -0.13659(19) 0.0396(10) Uani 1 1 d . . .
C45 C 0.2780(3) 0.4476(3) -0.1854(3) 0.0506(17) Uani 1 1 d . . .
C46 C 0.2631(3) 0.3932(3) -0.2007(4) 0.0585(19) Uani 1 1 d . . .
H23 H 0.2859 0.3641 -0.1760 0.070 Uiso 1 1 calc R . .
C47 C 0.2139(5) 0.3810(5) -0.2529(5) 0.091(3) Uani 1 1 d . . .
H24 H 0.2034 0.3435 -0.2637 0.110 Uiso 1 1 calc R . .
C48 C 0.1807(4) 0.4229(6) -0.2888(5) 0.097(3) Uani 1 1 d . . .
H25 H 0.1476 0.4141 -0.3244 0.117 Uiso 1 1 calc R . .
C49 C 0.1950(4) 0.4767(5) -0.2735(5) 0.091(3) Uani 1 1 d . . .
H26 H 0.1721 0.5054 -0.2989 0.109 Uiso 1 1 calc R . .
C50 C 0.2433(4) 0.4901(4) -0.2207(4) 0.071(2) Uani 1 1 d . . .
H27 H 0.2523 0.5277 -0.2089 0.086 Uiso 1 1 calc R . .
Cl2 Cl 0.21340(16) 0.36734(15) 0.21448(16) 0.1416(13) Uani 1 1 d DU . .
Cl3 Cl 0.19518(15) 0.27535(13) 0.3063(3) 0.1785(19) Uani 1 1 d DU . .
C52 C 0.4309(8) 0.0797(6) 0.1106(12) 0.264(9) Uani 1 1 d DU . .
H28 H 0.4023 0.0776 0.0646 0.317 Uiso 1 1 calc R . .
Cl4 Cl 0.4097(4) 0.0368(3) 0.1661(4) 0.297(4) Uani 1 1 d DU . .
Cl5 Cl 0.4270(5) 0.1455(3) 0.1452(5) 0.364(5) Uani 1 1 d DU . .
Cl6 Cl 0.4983(4) 0.0551(6) 0.0958(7) 0.493(9) Uani 1 1 d DU . .
Cl1 Cl 0.1412(3) 0.37932(15) 0.3218(2) 0.185(2) Uani 1 1 d DU . .
C51 C 0.1672(9) 0.3386(6) 0.2637(11) 0.104(6) Uani 0.48(2) 1 d PDU A 1
H29 H 0.1316 0.3274 0.2285 0.125 Uiso 0.48(2) 1 calc PR A 1
C53 C 0.2031(10) 0.3471(6) 0.3064(11) 0.135(7) Uani 0.52(2) 1 d PDU A 2
H30 H 0.2380 0.3587 0.3424 0.162 Uiso 0.52(2) 1 calc PR A 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C8 N1 C1 113.4(5) . . ?
C8 N1 B1 124.3(5) . . ?
C1 N1 B1 120.8(5) . . ?
N6 C1 N1 124.0(5) . . ?
N6 C1 C2 128.5(6) . . ?
N1 C1 C2 105.1(5) . . ?
C3 C2 C7 121.1(5) . . ?
C3 C2 C1 131.8(6) . . ?
C7 C2 C1 106.9(5) . . ?
F1 C3 C2 122.0(5) . . ?
F1 C3 C4 119.1(5) . . ?
C2 C3 C4 118.9(6) . . ?
F2 C4 C3 120.1(6) . . ?
F2 C4 C5 120.8(5) . . ?
C3 C4 C5 119.0(6) . . ?
C6 C5 F3 121.8(6) . . ?
C6 C5 C4 122.3(6) . . ?
F3 C5 C4 115.9(6) . . ?
C5 C6 F4 120.1(5) . . ?
C5 C6 C7 120.2(6) . . ?
F4 C6 C7 119.7(6) . . ?
C6 C7 C2 118.5(6) . . ?
C6 C7 C8 133.8(6) . . ?
C2 C7 C8 107.5(5) . . ?
N2 C8 N1 123.3(5) . . ?
N2 C8 C7 129.5(5) . . ?
N1 C8 C7 105.4(5) . . ?
C8 N2 C9 115.6(5) . . ?
C16 N3 C9 112.6(4) . . ?
C16 N3 B1 122.3(5) . . ?
C9 N3 B1 123.5(5) . . ?
N2 C9 N3 124.3(5) . . ?
N2 C9 C10 128.6(5) . . ?
N3 C9 C10 105.6(5) . . ?
C11 C10 C15 120.4(5) . . ?
C11 C10 C9 132.6(5) . . ?
C15 C10 C9 106.8(5) . . ?
F5 C11 C12 119.3(6) . . ?
F5 C11 C10 121.9(5) . . ?
C12 C11 C10 118.8(6) . . ?
F6 C12 C11 120.2(6) . . ?
F6 C12 C13 118.3(5) . . ?
C11 C12 C13 121.4(6) . . ?
F7 C13 C14 121.1(6) . . ?
F7 C13 C12 118.7(6) . . ?
C14 C13 C12 120.2(5) . . ?
F8 C14 C13 118.8(5) . . ?
F8 C14 C15 122.3(6) . . ?
C13 C14 C15 118.9(6) . . ?
C14 C15 C10 120.3(6) . . ?
C14 C15 C16 132.0(6) . . ?
C10 C15 C16 107.5(5) . . ?
N4 C16 N3 122.9(5) . . ?
N4 C16 C15 128.9(5) . . ?
N3 C16 C15 105.8(5) . . ?
C16 N4 C17 116.2(5) . . ?
C17 N5 C34 110.7(5) . . ?
C17 N5 B1 122.6(5) . . ?
C34 N5 B1 123.3(5) . . ?
N4 C17 N5 123.7(6) . . ?
N4 C17 C18 127.2(5) . . ?
N5 C17 C18 107.2(5) . . ?
C31 C18 C19 120.9(5) . . ?
C31 C18 C17 106.8(5) . . ?
C19 C18 C17 131.7(5) . . ?
C20 C19 C32 119.8(5) . . ?
C20 C19 C18 122.6(5) . . ?
C32 C19 C18 117.6(5) . . ?
C21 C20 C19 122.0(6) . . ?
C21 C20 H1 119.0 . . ?
C19 C20 H1 119.0 . . ?
C22 C21 C20 117.6(5) . . ?
C22 C21 C35 123.4(5) . . ?
C20 C21 C35 119.0(5) . . ?
C21 C22 C23 122.6(5) . . ?
C21 C22 H2 118.7 . . ?
C23 C22 H2 118.7 . . ?
C22 C23 C32 119.0(5) . . ?
C22 C23 C24 122.5(5) . . ?
C32 C23 C24 118.5(5) . . ?
C25 C24 C23 121.1(5) . . ?
C25 C24 C39 119.2(6) . . ?
C23 C24 C39 119.6(5) . . ?
C24 C25 C26 121.8(6) . . ?
C24 C25 C40 120.3(5) . . ?
C26 C25 C40 117.9(5) . . ?
C27 C26 C33 120.3(5) . . ?
C27 C26 C25 122.5(6) . . ?
C33 C26 C25 117.1(5) . . ?
C28 C27 C26 121.9(6) . . ?
C28 C27 H3 119.1 . . ?
C26 C27 H3 119.1 . . ?
C27 C28 C29 118.0(6) . . ?
C27 C28 C41 121.5(6) . . ?
C29 C28 C41 120.3(5) . . ?
C30 C29 C28 122.5(5) . . ?
C30 C29 H4 118.7 . . ?
C28 C29 H4 118.7 . . ?
C29 C30 C31 123.8(5) . . ?
C29 C30 C33 120.0(6) . . ?
C31 C30 C33 116.2(5) . . ?
C18 C31 C30 122.1(5) . . ?
C18 C31 C34 106.4(5) . . ?
C30 C31 C34 130.8(5) . . ?
C19 C32 C33 121.5(5) . . ?
C19 C32 C23 118.8(5) . . ?
C33 C32 C23 119.7(5) . . ?
C26 C33 C32 121.6(5) . . ?
C26 C33 C30 117.0(5) . . ?
C32 C33 C30 121.3(5) . . ?
N5 C34 N6 122.6(5) . . ?
N5 C34 C31 107.7(5) . . ?
N6 C34 C31 127.5(5) . . ?
C1 N6 C34 116.9(5) . . ?
C21 C35 C38 112.4(5) . . ?
C21 C35 C36 109.1(5) . . ?
C38 C35 C36 108.5(5) . . ?
C21 C35 C37 108.0(5) . . ?
C38 C35 C37 107.8(5) . . ?
C36 C35 C37 111.1(6) . . ?
C35 C36 H5 109.5 . . ?
C35 C36 H6 109.5 . . ?
H5 C36 H6 109.5 . . ?
C35 C36 H7 109.5 . . ?
H5 C36 H7 109.5 . . ?
H6 C36 H7 109.5 . . ?
C35 C37 H8 109.5 . . ?
C35 C37 H9 109.5 . . ?
H8 C37 H9 109.5 . . ?
C35 C37 H10 109.5 . . ?
H8 C37 H10 109.5 . . ?
H9 C37 H10 109.5 . . ?
C35 C38 H11 109.5 . . ?
C35 C38 H12 109.5 . . ?
H11 C38 H12 109.5 . . ?
C35 C38 H13 109.5 . . ?
H11 C38 H13 109.5 . . ?
H12 C38 H13 109.5 . . ?
N7 C39 C24 179.0(8) . . ?
N8 C40 C25 177.1(7) . . ?
C42 C41 C43 108.8(7) . . ?
C42 C41 C44 110.4(7) . . ?
C43 C41 C44 107.5(6) . . ?
C42 C41 C28 106.8(5) . . ?
C43 C41 C28 111.7(5) . . ?
C44 C41 C28 111.7(7) . . ?
C41 C42 H14 109.5 . . ?
C41 C42 H15 109.5 . . ?
H14 C42 H15 109.5 . . ?
C41 C42 H16 109.5 . . ?
H14 C42 H16 109.5 . . ?
H15 C42 H16 109.5 . . ?
C41 C43 H17 109.5 . . ?
C41 C43 H18 109.5 . . ?
H17 C43 H18 109.5 . . ?
C41 C43 H19 109.5 . . ?
H17 C43 H19 109.5 . . ?
H18 C43 H19 109.5 . . ?
C41 C44 H20 109.5 . . ?
C41 C44 H21 109.5 . . ?
H20 C44 H21 109.5 . . ?
C41 C44 H22 109.5 . . ?
H20 C44 H22 109.5 . . ?
H21 C44 H22 109.5 . . ?
O1 B1 N3 116.9(5) . . ?
O1 B1 N5 111.9(5) . . ?
N3 B1 N5 104.2(5) . . ?
O1 B1 N1 115.5(5) . . ?
N3 B1 N1 102.3(5) . . ?
N5 B1 N1 104.6(5) . . ?
C45 O1 B1 119.6(5) . . ?
O1 C45 C46 121.1(7) . . ?
O1 C45 C50 119.0(6) . . ?
C46 C45 C50 119.9(7) . . ?
C45 C46 C47 119.4(8) . . ?
C45 C46 H23 120.3 . . ?
C47 C46 H23 120.3 . . ?
C48 C47 C46 120.6(9) . . ?
C48 C47 H24 119.7 . . ?
C46 C47 H24 119.7 . . ?
C49 C48 C47 120.3(9) . . ?
C49 C48 H25 119.9 . . ?
C47 C48 H25 119.9 . . ?
C48 C49 C50 120.4(10) . . ?
C48 C49 H26 119.8 . . ?
C50 C49 H26 119.8 . . ?
C45 C50 C49 119.4(8) . . ?
C45 C50 H27 120.3 . . ?
C49 C50 H27 120.3 . . ?
C51 Cl2 C53 34.6(8) . . ?
C53 Cl3 C51 35.3(8) . . ?
Cl4 C52 Cl6 105.4(11) . . ?
Cl4 C52 Cl5 107.4(10) . . ?
Cl6 C52 Cl5 119.1(11) . . ?
Cl4 C52 H28 108.1 . . ?
Cl6 C52 H28 108.1 . . ?
Cl5 C52 H28 108.1 . . ?
C51 Cl1 C53 37.3(9) . . ?
Cl1 C51 Cl2 117.3(9) . . ?
Cl1 C51 Cl3 110.2(10) . . ?
Cl2 C51 Cl3 113.0(9) . . ?
Cl1 C51 H29 105.0 . . ?
Cl2 C51 H29 105.0 . . ?
Cl3 C51 H29 105.0 . . ?
Cl1 C53 Cl3 111.6(11) . . ?
Cl1 C53 Cl2 106.7(11) . . ?
Cl3 C53 Cl2 106.8(10) . . ?
Cl1 C53 H30 110.5 . . ?
Cl3 C53 H30 110.5 . . ?
Cl2 C53 H30 110.5 . . ?
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
N1 C8 1.363(7) . ?
N1 C1 1.370(8) . ?
N1 B1 1.525(8) . ?
C1 N6 1.324(7) . ?
C1 C2 1.462(8) . ?
C2 C3 1.373(8) . ?
C2 C7 1.419(9) . ?
C3 F1 1.338(7) . ?
C3 C4 1.391(8) . ?
C4 F2 1.325(7) . ?
C4 C5 1.410(9) . ?
C5 C6 1.325(9) . ?
C5 F3 1.358(7) . ?
C6 F4 1.353(7) . ?
C6 C7 1.393(8) . ?
C7 C8 1.454(8) . ?
C8 N2 1.332(7) . ?
N2 C9 1.345(7) . ?
N3 C16 1.365(7) . ?
N3 C9 1.368(7) . ?
N3 B1 1.499(8) . ?
C9 C10 1.472(8) . ?
C10 C11 1.381(9) . ?
C10 C15 1.409(8) . ?
C11 F5 1.351(7) . ?
C11 C12 1.364(8) . ?
C12 F6 1.342(7) . ?
C12 C13 1.398(9) . ?
C13 F7 1.312(6) . ?
C13 C14 1.381(9) . ?
C14 F8 1.330(7) . ?
C14 C15 1.382(8) . ?
C15 C16 1.458(8) . ?
C16 N4 1.334(7) . ?
N4 C17 1.345(7) . ?
N5 C17 1.354(7) . ?
N5 C34 1.357(7) . ?
N5 B1 1.499(8) . ?
C17 C18 1.447(8) . ?
C18 C31 1.405(8) . ?
C18 C19 1.438(8) . ?
C19 C20 1.406(8) . ?
C19 C32 1.409(8) . ?
C20 C21 1.404(8) . ?
C20 H1 0.9500 . ?
C21 C22 1.389(8) . ?
C21 C35 1.533(8) . ?
C22 C23 1.405(8) . ?
C22 H2 0.9500 . ?
C23 C32 1.430(8) . ?
C23 C24 1.431(8) . ?
C24 C25 1.370(8) . ?
C24 C39 1.434(9) . ?
C25 C26 1.449(8) . ?
C25 C40 1.460(9) . ?
C26 C27 1.406(8) . ?
C26 C33 1.414(8) . ?
C27 C28 1.375(8) . ?
C27 H3 0.9500 . ?
C28 C29 1.389(8) . ?
C28 C41 1.543(9) . ?
C29 C30 1.379(8) . ?
C29 H4 0.9500 . ?
C30 C31 1.436(8) . ?
C30 C33 1.438(8) . ?
C31 C34 1.441(8) . ?
C32 C33 1.423(8) . ?
C34 N6 1.359(7) . ?
C35 C38 1.539(8) . ?
C35 C36 1.540(9) . ?
C35 C37 1.542(8) . ?
C36 H5 0.9800 . ?
C36 H6 0.9800 . ?
C36 H7 0.9800 . ?
C37 H8 0.9800 . ?
C37 H9 0.9800 . ?
C37 H10 0.9800 . ?
C38 H11 0.9800 . ?
C38 H12 0.9800 . ?
C38 H13 0.9800 . ?
N7 C39 1.151(8) . ?
C40 N8 1.137(8) . ?
C41 C42 1.516(11) . ?
C41 C43 1.526(9) . ?
C41 C44 1.535(11) . ?
C42 H14 0.9800 . ?
C42 H15 0.9800 . ?
C42 H16 0.9800 . ?
C43 H17 0.9800 . ?
C43 H18 0.9800 . ?
C43 H19 0.9800 . ?
C44 H20 0.9800 . ?
C44 H21 0.9800 . ?
C44 H22 0.9800 . ?
B1 O1 1.423(7) . ?
O1 C45 1.373(8) . ?
C45 C46 1.375(9) . ?
C45 C50 1.397(10) . ?
C46 C47 1.399(11) . ?
C46 H23 0.9500 . ?
C47 C48 1.372(14) . ?
C47 H24 0.9500 . ?
C48 C49 1.359(14) . ?
C48 H25 0.9500 . ?
C49 C50 1.397(12) . ?
C49 H26 0.9500 . ?
C50 H27 0.9500 . ?
Cl2 C51 1.681(14) . ?
Cl2 C53 1.868(17) . ?
Cl3 C53 1.740(16) . ?
Cl3 C51 1.794(16) . ?
C52 Cl4 1.612(14) . ?
C52 Cl6 1.724(15) . ?
C52 Cl5 1.725(14) . ?
C52 H28 1.0000 . ?
Cl1 C51 1.664(14) . ?
Cl1 C53 1.690(17) . ?
C51 H29 1.0000 . ?
C53 H30 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
C8 N1 C1 N6 -150.3(5) . . . . ?
B1 N1 C1 N6 16.1(7) . . . . ?
C8 N1 C1 C2 13.4(6) . . . . ?
B1 N1 C1 C2 179.8(4) . . . . ?
N6 C1 C2 C3 -21.7(9) . . . . ?
N1 C1 C2 C3 175.6(5) . . . . ?
N6 C1 C2 C7 153.9(5) . . . . ?
N1 C1 C2 C7 -8.8(5) . . . . ?
C7 C2 C3 F1 177.6(5) . . . . ?
C1 C2 C3 F1 -7.3(9) . . . . ?
C7 C2 C3 C4 -2.2(8) . . . . ?
C1 C2 C3 C4 172.9(5) . . . . ?
F1 C3 C4 F2 -0.6(7) . . . . ?
C2 C3 C4 F2 179.2(5) . . . . ?
F1 C3 C4 C5 -177.8(5) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
F2 C4 C5 C6 -178.5(5) . . . . ?
C3 C4 C5 C6 -1.4(9) . . . . ?
F2 C4 C5 F3 0.8(8) . . . . ?
C3 C4 C5 F3 177.9(5) . . . . ?
F3 C5 C6 F4 0.7(9) . . . . ?
C4 C5 C6 F4 180.0(5) . . . . ?
F3 C5 C6 C7 -178.5(5) . . . . ?
C4 C5 C6 C7 0.7(9) . . . . ?
C5 C6 C7 C2 -0.8(8) . . . . ?
F4 C6 C7 C2 180.0(5) . . . . ?
C5 C6 C7 C8 -176.0(6) . . . . ?
F4 C6 C7 C8 4.7(9) . . . . ?
C3 C2 C7 C6 1.5(8) . . . . ?
C1 C2 C7 C6 -174.6(5) . . . . ?
C3 C2 C7 C8 178.0(5) . . . . ?
C1 C2 C7 C8 1.8(6) . . . . ?
C1 N1 C8 N2 153.4(5) . . . . ?
B1 N1 C8 N2 -12.4(8) . . . . ?
C1 N1 C8 C7 -12.3(6) . . . . ?
B1 N1 C8 C7 -178.2(5) . . . . ?
C6 C7 C8 N2 17.0(10) . . . . ?
C2 C7 C8 N2 -158.6(6) . . . . ?
C6 C7 C8 N1 -178.4(6) . . . . ?
C2 C7 C8 N1 5.9(6) . . . . ?
N1 C8 N2 C9 -7.8(8) . . . . ?
C7 C8 N2 C9 154.3(6) . . . . ?
C8 N2 C9 N3 8.6(8) . . . . ?
C8 N2 C9 C10 -155.5(6) . . . . ?
C16 N3 C9 N2 -154.9(5) . . . . ?
B1 N3 C9 N2 11.1(8) . . . . ?
C16 N3 C9 C10 12.3(6) . . . . ?
B1 N3 C9 C10 178.2(5) . . . . ?
N2 C9 C10 C11 -14.4(11) . . . . ?
N3 C9 C10 C11 179.2(6) . . . . ?
N2 C9 C10 C15 160.7(6) . . . . ?
N3 C9 C10 C15 -5.7(6) . . . . ?
C15 C10 C11 F5 -178.6(5) . . . . ?
C9 C10 C11 F5 -4.0(11) . . . . ?
C15 C10 C11 C12 2.6(9) . . . . ?
C9 C10 C11 C12 177.1(6) . . . . ?
F5 C11 C12 F6 1.1(10) . . . . ?
C10 C11 C12 F6 180.0(6) . . . . ?
F5 C11 C12 C13 178.3(6) . . . . ?
C10 C11 C12 C13 -2.8(10) . . . . ?
F6 C12 C13 F7 -1.4(10) . . . . ?
C11 C12 C13 F7 -178.6(6) . . . . ?
F6 C12 C13 C14 179.1(6) . . . . ?
C11 C12 C13 C14 1.8(11) . . . . ?
F7 C13 C14 F8 -0.4(10) . . . . ?
C12 C13 C14 F8 179.2(6) . . . . ?
F7 C13 C14 C15 179.9(6) . . . . ?
C12 C13 C14 C15 -0.6(10) . . . . ?
F8 C14 C15 C10 -179.4(5) . . . . ?
C13 C14 C15 C10 0.4(9) . . . . ?
F8 C14 C15 C16 7.1(10) . . . . ?
C13 C14 C15 C16 -173.2(6) . . . . ?
C11 C10 C15 C14 -1.4(9) . . . . ?
C9 C10 C15 C14 -177.2(5) . . . . ?
C11 C10 C15 C16 173.6(5) . . . . ?
C9 C10 C15 C16 -2.2(6) . . . . ?
C9 N3 C16 N4 150.2(5) . . . . ?
B1 N3 C16 N4 -15.9(8) . . . . ?
C9 N3 C16 C15 -13.6(6) . . . . ?
B1 N3 C16 C15 -179.8(5) . . . . ?
C14 C15 C16 N4 20.9(10) . . . . ?
C10 C15 C16 N4 -153.3(6) . . . . ?
C14 C15 C16 N3 -176.5(6) . . . . ?
C10 C15 C16 N3 9.3(6) . . . . ?
N3 C16 N4 C17 -8.5(7) . . . . ?
C15 C16 N4 C17 151.4(5) . . . . ?
C16 N4 C17 N5 13.7(7) . . . . ?
C16 N4 C17 C18 -148.4(5) . . . . ?
C34 N5 C17 N4 -154.4(5) . . . . ?
B1 N5 C17 N4 5.5(8) . . . . ?
C34 N5 C17 C18 10.8(6) . . . . ?
B1 N5 C17 C18 170.7(5) . . . . ?
N4 C17 C18 C31 158.2(5) . . . . ?
N5 C17 C18 C31 -6.3(6) . . . . ?
N4 C17 C18 C19 -12.9(9) . . . . ?
N5 C17 C18 C19 -177.4(5) . . . . ?
C31 C18 C19 C20 174.6(5) . . . . ?
C17 C18 C19 C20 -15.4(9) . . . . ?
C31 C18 C19 C32 -5.9(7) . . . . ?
C17 C18 C19 C32 164.1(5) . . . . ?
C32 C19 C20 C21 0.8(8) . . . . ?
C18 C19 C20 C21 -179.7(5) . . . . ?
C19 C20 C21 C22 -2.5(8) . . . . ?
C19 C20 C21 C35 176.4(5) . . . . ?
C20 C21 C22 C23 1.5(8) . . . . ?
C35 C21 C22 C23 -177.4(5) . . . . ?
C21 C22 C23 C32 1.3(8) . . . . ?
C21 C22 C23 C24 -179.4(5) . . . . ?
C22 C23 C24 C25 -176.3(5) . . . . ?
C32 C23 C24 C25 2.9(8) . . . . ?
C22 C23 C24 C39 -0.3(8) . . . . ?
C32 C23 C24 C39 179.0(5) . . . . ?
C23 C24 C25 C26 1.7(8) . . . . ?
C39 C24 C25 C26 -174.3(5) . . . . ?
C23 C24 C25 C40 179.6(5) . . . . ?
C39 C24 C25 C40 3.6(8) . . . . ?
C24 C25 C26 C27 174.1(5) . . . . ?
C40 C25 C26 C27 -3.9(8) . . . . ?
C24 C25 C26 C33 -4.5(8) . . . . ?
C40 C25 C26 C33 177.5(5) . . . . ?
C33 C26 C27 C28 1.3(8) . . . . ?
C25 C26 C27 C28 -177.2(5) . . . . ?
C26 C27 C28 C29 -4.4(8) . . . . ?
C26 C27 C28 C41 171.8(5) . . . . ?
C27 C28 C29 C30 3.3(8) . . . . ?
C41 C28 C29 C30 -172.9(5) . . . . ?
C28 C29 C30 C31 -179.0(5) . . . . ?
C28 C29 C30 C33 0.8(8) . . . . ?
C19 C18 C31 C30 1.4(8) . . . . ?
C17 C18 C31 C30 -170.9(5) . . . . ?
C19 C18 C31 C34 172.2(4) . . . . ?
C17 C18 C31 C34 -0.1(6) . . . . ?
C29 C30 C31 C18 -176.0(5) . . . . ?
C33 C30 C31 C18 4.2(7) . . . . ?
C29 C30 C31 C34 15.7(9) . . . . ?
C33 C30 C31 C34 -164.1(5) . . . . ?
C20 C19 C32 C33 -175.6(5) . . . . ?
C18 C19 C32 C33 4.8(7) . . . . ?
C20 C19 C32 C23 2.0(7) . . . . ?
C18 C19 C32 C23 -177.5(5) . . . . ?
C22 C23 C32 C19 -3.0(7) . . . . ?
C24 C23 C32 C19 177.7(5) . . . . ?
C22 C23 C32 C33 174.7(5) . . . . ?
C24 C23 C32 C33 -4.6(7) . . . . ?
C27 C26 C33 C32 -175.9(5) . . . . ?
C25 C26 C33 C32 2.7(7) . . . . ?
C27 C26 C33 C30 2.8(7) . . . . ?
C25 C26 C33 C30 -178.6(5) . . . . ?
C19 C32 C33 C26 179.4(5) . . . . ?
C23 C32 C33 C26 1.8(7) . . . . ?
C19 C32 C33 C30 0.8(8) . . . . ?
C23 C32 C33 C30 -176.8(5) . . . . ?
C29 C30 C33 C26 -3.8(7) . . . . ?
C31 C30 C33 C26 176.0(5) . . . . ?
C29 C30 C33 C32 174.9(5) . . . . ?
C31 C30 C33 C32 -5.3(7) . . . . ?
C17 N5 C34 N6 153.8(5) . . . . ?
B1 N5 C34 N6 -6.0(8) . . . . ?
C17 N5 C34 C31 -10.9(6) . . . . ?
B1 N5 C34 C31 -170.7(5) . . . . ?
C18 C31 C34 N5 6.5(6) . . . . ?
C30 C31 C34 N5 176.1(5) . . . . ?
C18 C31 C34 N6 -157.3(5) . . . . ?
C30 C31 C34 N6 12.4(9) . . . . ?
N1 C1 N6 C34 7.5(7) . . . . ?
C2 C1 N6 C34 -152.2(5) . . . . ?
N5 C34 N6 C1 -12.9(7) . . . . ?
C31 C34 N6 C1 148.7(5) . . . . ?
C22 C21 C35 C38 -1.6(8) . . . . ?
C20 C21 C35 C38 179.5(5) . . . . ?
C22 C21 C35 C36 -121.9(6) . . . . ?
C20 C21 C35 C36 59.2(7) . . . . ?
C22 C21 C35 C37 117.2(6) . . . . ?
C20 C21 C35 C37 -61.7(7) . . . . ?
C25 C24 C39 N7 -176(100) . . . . ?
C23 C24 C39 N7 8(39) . . . . ?
C24 C25 C40 N8 128(13) . . . . ?
C26 C25 C40 N8 -53(13) . . . . ?
C27 C28 C41 C42 -94.3(7) . . . . ?
C29 C28 C41 C42 81.7(8) . . . . ?
C27 C28 C41 C43 24.6(9) . . . . ?
C29 C28 C41 C43 -159.4(6) . . . . ?
C27 C28 C41 C44 144.9(6) . . . . ?
C29 C28 C41 C44 -39.1(8) . . . . ?
C16 N3 B1 O1 -93.9(6) . . . . ?
C9 N3 B1 O1 101.5(6) . . . . ?
C16 N3 B1 N5 30.2(7) . . . . ?
C9 N3 B1 N5 -134.5(5) . . . . ?
C16 N3 B1 N1 138.9(5) . . . . ?
C9 N3 B1 N1 -25.8(7) . . . . ?
C17 N5 B1 O1 102.0(6) . . . . ?
C34 N5 B1 O1 -100.6(6) . . . . ?
C17 N5 B1 N3 -25.2(6) . . . . ?
C34 N5 B1 N3 132.2(5) . . . . ?
C17 N5 B1 N1 -132.3(5) . . . . ?
C34 N5 B1 N1 25.2(7) . . . . ?
C8 N1 B1 O1 -101.4(6) . . . . ?
C1 N1 B1 O1 93.8(6) . . . . ?
C8 N1 B1 N3 26.7(7) . . . . ?
C1 N1 B1 N3 -138.1(5) . . . . ?
C8 N1 B1 N5 135.2(5) . . . . ?
C1 N1 B1 N5 -29.7(6) . . . . ?
N3 B1 O1 C45 -61.3(7) . . . . ?
N5 B1 O1 C45 178.6(5) . . . . ?
N1 B1 O1 C45 59.1(7) . . . . ?
B1 O1 C45 C46 -88.9(7) . . . . ?
B1 O1 C45 C50 92.1(7) . . . . ?
O1 C45 C46 C47 -177.3(6) . . . . ?
C50 C45 C46 C47 1.7(10) . . . . ?
C45 C46 C47 C48 0.0(11) . . . . ?
C46 C47 C48 C49 -0.5(13) . . . . ?
C47 C48 C49 C50 -0.6(14) . . . . ?
O1 C45 C50 C49 176.2(6) . . . . ?
C46 C45 C50 C49 -2.8(11) . . . . ?
C48 C49 C50 C45 2.3(13) . . . . ?
C53 Cl1 C51 Cl2 -71.4(15) . . . . ?
C53 Cl1 C51 Cl3 59.8(14) . . . . ?
C53 Cl2 C51 Cl1 65.9(15) . . . . ?
C53 Cl2 C51 Cl3 -63.9(15) . . . . ?
C53 Cl3 C51 Cl1 -61.7(14) . . . . ?
C53 Cl3 C51 Cl2 71.8(15) . . . . ?
C51 Cl1 C53 Cl3 -64.1(14) . . . . ?
C51 Cl1 C53 Cl2 52.3(12) . . . . ?
C51 Cl3 C53 Cl1 61.0(14) . . . . ?
C51 Cl3 C53 Cl2 -55.3(12) . . . . ?
C51 Cl2 C53 Cl1 -56.5(13) . . . . ?
C51 Cl2 C53 Cl3 63.0(13) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.419 0.250 164 41 ' '
2 0.500 0.919 0.250 164 41 ' '
3 0.000 0.581 0.750 164 41 ' '
4 0.500 0.081 0.750 164 41 ' '
