#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:47:17 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/28/4032881.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_4032881
loop_
_publ_author_name
'Sheng, Wanle'
'Cui, Jiuen'
'Ruan, Zheng'
'Yan, Lifeng'
'Wu, Qinghua'
'Yu, Changjiang'
'Wei, Yun'
'Hao, Erhong'
'Jiao, Lijuan'
_publ_section_title
;
 [a]-Phenanthrene-Fused BF2 Azadipyrromethene (AzaBODIPY) Dyes as Bright
 Near-Infrared Fluorophores.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10341
_journal_page_last               10349
_journal_paper_doi               10.1021/acs.joc.7b01803
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C60 H62 B F2 N3 O8'
_chemical_formula_weight         1001.94
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 121.450(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.309(3)
_cell_length_b                   23.961(3)
_cell_length_c                   13.3093(19)
_cell_measurement_reflns_used    6216
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.89
_cell_measurement_theta_min      2.47
_cell_volume                     5797.2(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20265
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9803
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2120
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_platon_squeeze_details
;
;
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5113
_refine_ls_number_restraints     550
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0591
_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)+(0.1070P)²+0.9262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1908
_reflns_number_gt                3323
_reflns_number_total             5113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01803_si_002.cif
_cod_data_source_block           140324b_0m_compound_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032881--4032884.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4032881
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
B1 B 0.0000 0.35412(16) 0.2500 0.0674(11) Uani 1 2 d SU . .
C1 C 0.10891(12) 0.32771(9) 0.46400(19) 0.0558(6) Uani 1 1 d . A .
C2 C 0.14472(12) 0.27797(9) 0.52512(19) 0.0553(6) Uani 1 1 d . . .
C3 C 0.10813(12) 0.23373(9) 0.44901(18) 0.0527(5) Uani 1 1 d . . .
C4 C 0.05038(12) 0.25749(8) 0.34369(19) 0.0529(5) Uani 1 1 d . A .
C5 C 0.12792(12) 0.38531(9) 0.5067(2) 0.0620(6) Uani 1 1 d . . .
C6 C 0.0811(2) 0.41954(14) 0.5195(4) 0.0979(12) Uani 0.864(4) 1 d PU A 5
H6 H 0.0344 0.4066 0.4973 0.118 Uiso 0.864(4) 1 calc PR A 5
C7 C 0.1018(2) 0.47323(17) 0.5649(4) 0.1193(15) Uani 0.864(4) 1 d PU A 5
H7 H 0.0698 0.4956 0.5751 0.143 Uiso 0.864(4) 1 calc PR A 5
C8 C 0.16886(19) 0.49257(13) 0.5940(4) 0.1132(12) Uani 1 1 d DU . .
C9 C 0.2166(2) 0.45909(15) 0.5846(4) 0.1059(13) Uani 0.864(4) 1 d PU A 5
H9 H 0.2634 0.4721 0.6077 0.127 Uiso 0.864(4) 1 calc PR A 5
C10 C 0.19653(19) 0.40678(13) 0.5418(4) 0.0876(11) Uani 0.864(4) 1 d PU A 5
H10 H 0.2301 0.3844 0.5358 0.105 Uiso 0.864(4) 1 calc PR A 5
C11 C 0.1546(3) 0.5777(2) 0.6714(7) 0.191(3) Uani 0.864(4) 1 d PDU A 5
H11A H 0.1786 0.6131 0.6987 0.286 Uiso 0.864(4) 1 calc PR A 5
H11B H 0.1529 0.5592 0.7340 0.286 Uiso 0.864(4) 1 calc PR A 5
H11C H 0.1055 0.5832 0.6059 0.286 Uiso 0.864(4) 1 calc PR A 5
C12 C 0.20953(12) 0.27484(9) 0.6461(2) 0.0569(6) Uani 1 1 d . . .
C13 C 0.27022(12) 0.24277(10) 0.6712(2) 0.0630(6) Uani 1 1 d . . .
H13 H 0.2705 0.2237 0.6106 0.076 Uiso 1 1 calc R . .
C14 C 0.33016(14) 0.23869(11) 0.7844(2) 0.0678(7) Uani 1 1 d . . .
H14 H 0.3700 0.2169 0.7980 0.081 Uiso 1 1 calc R . .
C15 C 0.33300(13) 0.26590(11) 0.8779(2) 0.0671(7) Uani 1 1 d . B .
C16 C 0.27324(15) 0.29938(12) 0.8513(2) 0.0804(8) Uani 1 1 d . . .
H16 H 0.2738 0.3195 0.9116 0.096 Uiso 1 1 calc R . .
C17 C 0.21276(14) 0.30387(12) 0.7383(2) 0.0742(7) Uani 1 1 d . . .
H17 H 0.1737 0.3268 0.7242 0.089 Uiso 1 1 calc R . .
C18 C 0.39795(15) 0.26081(14) 1.0038(2) 0.0839(8) Uani 1 1 d U . .
C19 C 0.3735(3) 0.2419(4) 1.0844(5) 0.131(3) Uani 0.713(7) 1 d PU B 3
H19A H 0.4153 0.2390 1.1631 0.197 Uiso 0.713(7) 1 calc PR B 3
H19B H 0.3501 0.2061 1.0592 0.197 Uiso 0.713(7) 1 calc PR B 3
H19C H 0.3392 0.2684 1.0829 0.197 Uiso 0.713(7) 1 calc PR B 3
C20 C 0.4599(3) 0.2251(4) 1.0166(4) 0.129(2) Uani 0.713(7) 1 d PU B 3
H20A H 0.4748 0.2383 0.9641 0.194 Uiso 0.713(7) 1 calc PR B 3
H20B H 0.4435 0.1871 0.9975 0.194 Uiso 0.713(7) 1 calc PR B 3
H20C H 0.5008 0.2270 1.0962 0.194 Uiso 0.713(7) 1 calc PR B 3
C21 C 0.4314(4) 0.3212(3) 1.0476(6) 0.146(3) Uani 0.713(7) 1 d PU B 3
H21A H 0.4485 0.3355 0.9987 0.219 Uiso 0.713(7) 1 calc PR B 3
H21B H 0.4718 0.3192 1.1277 0.219 Uiso 0.713(7) 1 calc PR B 3
H21C H 0.3942 0.3456 1.0431 0.219 Uiso 0.713(7) 1 calc PR B 3
C19' C 0.4615(8) 0.2824(11) 1.0074(13) 0.137(5) Uani 0.287(7) 1 d PU B 4
H19D H 0.5032 0.2796 1.0862 0.205 Uiso 0.287(7) 1 calc PR B 4
H19E H 0.4533 0.3208 0.9835 0.205 Uiso 0.287(7) 1 calc PR B 4
H19F H 0.4706 0.2613 0.9550 0.205 Uiso 0.287(7) 1 calc PR B 4
C20' C 0.3860(9) 0.2942(10) 1.0890(11) 0.134(5) Uani 0.287(7) 1 d PU B 4
H20D H 0.3408 0.2829 1.0822 0.201 Uiso 0.287(7) 1 calc PR B 4
H20E H 0.3837 0.3332 1.0708 0.201 Uiso 0.287(7) 1 calc PR B 4
H20F H 0.4261 0.2877 1.1679 0.201 Uiso 0.287(7) 1 calc PR B 4
C21' C 0.3918(10) 0.1965(9) 1.0405(14) 0.153(6) Uani 0.287(7) 1 d PU B 4
H21D H 0.3453 0.1914 1.0345 0.230 Uiso 0.287(7) 1 calc PR B 4
H21E H 0.4308 0.1895 1.1200 0.230 Uiso 0.287(7) 1 calc PR B 4
H21F H 0.3957 0.1709 0.9884 0.230 Uiso 0.287(7) 1 calc PR B 4
C22 C 0.11809(11) 0.17301(9) 0.46613(19) 0.0546(6) Uani 1 1 d . . .
C23 C 0.12755(12) 0.14764(9) 0.56694(19) 0.0589(6) Uani 1 1 d . . .
H23 H 0.1329 0.1692 0.6290 0.071 Uiso 1 1 calc R . .
C24 C 0.12889(14) 0.08990(10) 0.5745(2) 0.0658(6) Uani 1 1 d . . .
C25 C 0.12326(15) 0.05745(10) 0.4843(2) 0.0711(7) Uani 1 1 d . C .
C26 C 0.11354(16) 0.08304(10) 0.3837(2) 0.0726(7) Uani 1 1 d . C .
C27 C 0.11162(14) 0.14073(10) 0.3753(2) 0.0655(6) Uani 1 1 d . . .
H27 H 0.1059 0.1578 0.3082 0.079 Uiso 1 1 calc R . .
C28 C 0.1376(2) 0.09116(13) 0.7609(3) 0.1072(11) Uani 1 1 d . . .
H28A H 0.1791 0.1159 0.7941 0.161 Uiso 1 1 calc R . .
H28B H 0.1426 0.0657 0.8204 0.161 Uiso 1 1 calc R . .
H28C H 0.0932 0.1125 0.7316 0.161 Uiso 1 1 calc R . .
C29 C 0.1979(4) -0.0236(2) 0.5752(5) 0.107(2) Uani 0.599(7) 1 d P C 1
H29A H 0.1948 -0.0636 0.5757 0.160 Uiso 0.599(7) 1 calc PR C 1
H29B H 0.2150 -0.0095 0.6528 0.160 Uiso 0.599(7) 1 calc PR C 1
H29C H 0.2317 -0.0130 0.5514 0.160 Uiso 0.599(7) 1 calc PR C 1
C29' C 0.0469(6) -0.0251(3) 0.4141(10) 0.119(4) Uani 0.401(7) 1 d P C 2
H29D H 0.0497 -0.0650 0.4211 0.178 Uiso 0.401(7) 1 calc PR C 2
H29E H 0.0275 -0.0148 0.3335 0.178 Uiso 0.401(7) 1 calc PR C 2
H29F H 0.0152 -0.0111 0.4396 0.178 Uiso 0.401(7) 1 calc PR C 2
C30 C 0.0853(4) 0.0737(2) 0.1838(4) 0.111(2) Uani 0.805(13) 1 d PDU D 7
H30A H 0.0832 0.0455 0.1308 0.166 Uiso 0.805(13) 1 calc PR D 7
H30B H 0.1211 0.1013 0.1953 0.166 Uiso 0.805(13) 1 calc PR D 7
H30C H 0.0379 0.0910 0.1509 0.166 Uiso 0.805(13) 1 calc PR D 7
F1 F 0.04110(12) 0.38611(9) 0.22178(15) 0.1452(9) Uani 1 1 d U . .
N1 N 0.05174(10) 0.31541(7) 0.35396(16) 0.0546(5) Uani 1 1 d . . .
N2 N 0.0000 0.22963(10) 0.2500 0.0548(6) Uani 1 2 d S . .
O1 O 0.19343(15) 0.54519(10) 0.6365(3) 0.1608(12) Uani 1 1 d DU A .
O2 O 0.13444(12) 0.06068(7) 0.66715(16) 0.0876(6) Uani 1 1 d . . .
O3 O 0.12403(13) -0.00011(7) 0.49123(19) 0.0933(6) Uani 1 1 d . . .
O4 O 0.10643(14) 0.04801(8) 0.29755(18) 0.1009(7) Uani 1 1 d DU . .
C30' C 0.1310(7) 0.0741(4) 0.2285(10) 0.118(10) Uani 0.195(13) 1 d PDU D 8
H30D H 0.1270 0.0484 0.1702 0.176 Uiso 0.195(13) 1 calc PR D 8
H30E H 0.1814 0.0853 0.2784 0.176 Uiso 0.195(13) 1 calc PR D 8
H30F H 0.1013 0.1064 0.1903 0.176 Uiso 0.195(13) 1 calc PR D 8
C9' C 0.1634(7) 0.4150(4) 0.4758(10) 0.119(4) Uani 0.136(4) 1 d PRU A 6
H9' H 0.1794 0.3968 0.4314 0.143 Uiso 0.136(4) 1 calc PR A 6
C7' C 0.1147(7) 0.4002(4) 0.5941(10) 0.118(4) Uani 0.136(4) 1 d PRU A 6
H7' H 0.0954 0.3740 0.6223 0.141 Uiso 0.136(4) 1 calc PR A 6
C10' C 0.1829(7) 0.4732(4) 0.4990(10) 0.123(4) Uani 0.136(4) 1 d PRDU A 6
H10' H 0.2010 0.4951 0.4619 0.148 Uiso 0.136(4) 1 calc PR A 6
C6' C 0.1306(7) 0.4568(4) 0.6430(10) 0.118(4) Uani 0.136(4) 1 d PRU A 6
H6' H 0.1189 0.4697 0.6973 0.142 Uiso 0.136(4) 1 calc PR A 6
C11' C 0.1889(7) 0.5615(4) 0.7432(10) 0.121(6) Uani 0.136(4) 1 d PRDU A 6
H11D H 0.2070 0.5989 0.7667 0.181 Uiso 0.136(4) 1 calc PR A 6
H11E H 0.2181 0.5363 0.8069 0.181 Uiso 0.136(4) 1 calc PR A 6
H11F H 0.1386 0.5597 0.7231 0.181 Uiso 0.136(4) 1 calc PR A 6
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'
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'
B B 0.0013 0.0007 '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
F1 B1 F1 111.2(4) . 2
F1 B1 N1 110.66(11) . 2
F1 B1 N1 108.93(11) 2 2
F1 B1 N1 108.93(11) . .
F1 B1 N1 110.66(11) 2 .
N1 B1 N1 106.4(3) 2 .
N1 C1 C2 110.25(19) . .
N1 C1 C5 122.13(19) . .
C2 C1 C5 127.6(2) . .
C3 C2 C1 107.04(19) . .
C3 C2 C12 127.23(19) . .
C1 C2 C12 125.7(2) . .
C2 C3 C4 106.40(18) . .
C2 C3 C22 131.33(19) . .
C4 C3 C22 122.13(19) . .
N2 C4 N1 124.0(2) . .
N2 C4 C3 126.04(19) . .
N1 C4 C3 109.91(18) . .
C9' C5 C6 107.7(6) . .
C9' C5 C7' 123.6(8) . .
C6 C5 C7' 42.0(5) . .
C9' C5 C10 35.6(6) . .
C6 C5 C10 116.5(3) . .
C7' C5 C10 105.3(6) . .
C9' C5 C1 119.9(5) . .
C6 C5 C1 122.7(2) . .
C7' C5 C1 115.7(5) . .
C10 C5 C1 120.7(2) . .
C5 C6 C7 121.5(3) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C8 C7 C6 119.2(3) . .
C8 C7 H7 120.4 . .
C6 C7 H7 120.4 . .
C9 C8 C7 120.3(3) . .
C9 C8 O1 116.1(3) . .
C7 C8 O1 123.5(3) . .
C9 C8 C10' 41.9(5) . .
C7 C8 C10' 107.2(6) . .
O1 C8 C10' 115.3(5) . .
C9 C8 C6' 107.4(5) . .
C7 C8 C6' 38.6(5) . .
O1 C8 C6' 120.6(5) . .
C10' C8 C6' 124.1(7) . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 120.0 . .
C8 C9 H9 120.0 . .
C9 C10 C5 122.4(3) . .
C9 C10 H10 118.8 . .
C5 C10 H10 118.8 . .
O1 C11 H11A 109.5 . .
O1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C17 C12 C13 117.2(2) . .
C17 C12 C2 121.8(2) . .
C13 C12 C2 120.9(2) . .
C14 C13 C12 121.2(2) . .
C14 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C15 C14 C13 122.1(2) . .
C15 C14 H14 118.9 . .
C13 C14 H14 118.9 . .
C14 C15 C16 116.2(2) . .
C14 C15 C18 122.8(2) . .
C16 C15 C18 121.0(2) . .
C17 C16 C15 122.2(2) . .
C17 C16 H16 118.9 . .
C15 C16 H16 118.9 . .
C12 C17 C16 120.9(2) . .
C12 C17 H17 119.5 . .
C16 C17 H17 119.5 . .
C19' C18 C19 140.4(7) . .
C19' C18 C20 56.1(10) . .
C19 C18 C20 111.2(4) . .
C19' C18 C20' 108.1(12) . .
C19 C18 C20' 50.3(8) . .
C20 C18 C20' 134.1(6) . .
C19' C18 C15 108.1(6) . .
C19 C18 C15 111.0(3) . .
C20 C18 C15 114.2(3) . .
C20' C18 C15 111.7(6) . .
C19' C18 C21 54.5(9) . .
C19 C18 C21 105.8(5) . .
C20 C18 C21 106.2(5) . .
C20' C18 C21 57.3(9) . .
C15 C18 C21 107.9(3) . .
C19' C18 C21' 123.5(12) . .
C19 C18 C21' 52.2(8) . .
C20 C18 C21' 68.5(8) . .
C20' C18 C21' 101.7(11) . .
C15 C18 C21' 103.6(5) . .
C21 C18 C21' 147.0(6) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C18 C19' H19D 109.5 . .
C18 C19' H19E 109.5 . .
H19D C19' H19E 109.5 . .
C18 C19' H19F 109.5 . .
H19D C19' H19F 109.5 . .
H19E C19' H19F 109.5 . .
C18 C20' H20D 109.5 . .
C18 C20' H20E 109.5 . .
H20D C20' H20E 109.5 . .
C18 C20' H20F 109.5 . .
H20D C20' H20F 109.5 . .
H20E C20' H20F 109.5 . .
C18 C21' H21D 109.5 . .
C18 C21' H21E 109.5 . .
H21D C21' H21E 109.5 . .
C18 C21' H21F 109.5 . .
H21D C21' H21F 109.5 . .
H21E C21' H21F 109.5 . .
C27 C22 C23 119.9(2) . .
C27 C22 C3 118.58(19) . .
C23 C22 C3 121.28(19) . .
C24 C23 C22 119.6(2) . .
C24 C23 H23 120.2 . .
C22 C23 H23 120.2 . .
O2 C24 C25 115.0(2) . .
O2 C24 C23 124.4(2) . .
C25 C24 C23 120.7(2) . .
C24 C25 O3 120.8(2) . .
C24 C25 C26 119.4(2) . .
O3 C25 C26 119.7(2) . .
O4 C26 C27 124.1(2) . .
O4 C26 C25 115.8(2) . .
C27 C26 C25 120.1(2) . .
C22 C27 C26 120.2(2) . .
C22 C27 H27 119.9 . .
C26 C27 H27 119.9 . .
O2 C28 H28A 109.5 . .
O2 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
O2 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O3 C29 H29A 109.5 . .
O3 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
O3 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
O3 C29' H29D 109.5 . .
O3 C29' H29E 109.5 . .
H29D C29' H29E 109.5 . .
O3 C29' H29F 109.5 . .
H29D C29' H29F 109.5 . .
H29E C29' H29F 109.5 . .
O4 C30 H30A 109.5 . .
O4 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
O4 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C1 N1 C4 106.40(17) . .
C1 N1 B1 130.66(19) . .
C4 N1 B1 122.70(19) . .
C4 N2 C4 119.5(3) . 2
C8 O1 C11 119.4(4) . .
C8 O1 C11' 115.2(5) . .
C11 O1 C11' 37.0(5) . .
C24 O2 C28 118.2(2) . .
C25 O3 C29 113.5(3) . .
C25 O3 C29' 111.9(4) . .
C29 O3 C29' 134.4(4) . .
C26 O4 C30' 110.9(4) . .
C26 O4 C30 116.6(3) . .
C30' O4 C30 33.5(5) . .
O4 C30' H30D 109.5 . .
O4 C30' H30E 109.5 . .
H30D C30' H30E 109.5 . .
O4 C30' H30F 109.5 . .
H30D C30' H30F 109.5 . .
H30E C30' H30F 109.5 . .
C5 C9' C10' 129.3(4) . .
C5 C9' H9' 115.3 . .
C10' C9' H9' 115.3 . .
C5 C7' C6' 120.9(4) . .
C5 C7' H7' 119.6 . .
C6' C7' H7' 119.6 . .
C9' C10' C8 108.4(4) . .
C9' C10' H10' 125.8 . .
C8 C10' H10' 125.8 . .
C7' C6' C8 112.1(3) . .
C7' C6' H6' 123.9 . .
C8 C6' H6' 123.9 . .
O1 C11' H11D 109.5 . .
O1 C11' H11E 109.5 . .
H11D C11' H11E 109.5 . .
O1 C11' H11F 109.5 . .
H11D C11' H11F 109.5 . .
H11E C11' H11F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.356(3) .
B1 F1 1.356(3) 2
B1 N1 1.549(3) 2
B1 N1 1.549(3) .
C1 N1 1.362(3) .
C1 C2 1.420(3) .
C1 C5 1.467(3) .
C2 C3 1.390(3) .
C2 C12 1.478(3) .
C3 C4 1.415(3) .
C3 C22 1.471(3) .
C4 N2 1.325(2) .
C4 N1 1.393(3) .
C5 C9' 1.253(11) .
C5 C6 1.369(4) .
C5 C7' 1.379(10) .
C5 C10 1.381(4) .
C6 C7 1.392(5) .
C6 H6 0.9300 .
C7 C8 1.353(5) .
C7 H7 0.9300 .
C8 C9 1.352(5) .
C8 O1 1.369(4) .
C8 C10' 1.516(10) .
C8 C6' 1.544(12) .
C9 C10 1.351(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 O1 1.380(6) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C17 1.381(3) .
C12 C13 1.387(3) .
C13 C14 1.379(3) .
C13 H13 0.9300 .
C14 C15 1.379(4) .
C14 H14 0.9300 .
C15 C16 1.386(4) .
C15 C18 1.522(3) .
C16 C17 1.383(3) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19' 1.426(16) .
C18 C19 1.487(6) .
C18 C20 1.507(6) .
C18 C20' 1.514(17) .
C18 C21 1.585(7) .
C18 C21' 1.643(19) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C19' H19D 0.9600 .
C19' H19E 0.9600 .
C19' H19F 0.9600 .
C20' H20D 0.9600 .
C20' H20E 0.9600 .
C20' H20F 0.9600 .
C21' H21D 0.9600 .
C21' H21E 0.9600 .
C21' H21F 0.9600 .
C22 C27 1.380(3) .
C22 C23 1.389(3) .
C23 C24 1.386(3) .
C23 H23 0.9300 .
C24 O2 1.369(3) .
C24 C25 1.381(3) .
C25 O3 1.382(3) .
C25 C26 1.387(3) .
C26 O4 1.364(3) .
C26 C27 1.386(3) .
C27 H27 0.9300 .
C28 O2 1.416(3) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 O3 1.486(6) .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C29' O3 1.533(10) .
C29' H29D 0.9600 .
C29' H29E 0.9600 .
C29' H29F 0.9600 .
C30 O4 1.471(5) .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
N2 C4 1.325(2) 2
O1 C11' 1.524(10) .
O4 C30' 1.418(11) .
C30' H30D 0.9600 .
C30' H30E 0.9600 .
C30' H30F 0.9600 .
C9' C10' 1.4421 .
C9' H9' 0.9300 .
C7' C6' 1.4649 .
C7' H7' 0.9300 .
C10' H10' 0.9300 .
C6' H6' 0.9300 .
C11' H11D 0.9600 .
C11' H11E 0.9600 .
C11' H11F 0.9600 .
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
1 0.500 0.070 0.250 145.7 19.5
2 1.000 0.570 0.250 145.7 19.5
3 0.500 0.930 0.750 145.7 19.5
4 1.000 0.430 0.750 145.7 19.5
