#------------------------------------------------------------------------------
#$Date: 2015-09-24 14:27:26 +0300 (Thu, 24 Sep 2015) $
#$Revision: 158276 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117827.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_7117827
loop_
_publ_author_name
'A. Mirloup'
'Q. Huaulme'
'N. Leclerc'
'P. Leveque'
'T. Heiser'
'P. Retailleau'
'R. Ziessel'
_publ_section_title
;
 Thienyl-BOPHY dyes as promising templates for bulk heterojunction solar
 cells
;
_journal_name_full               Chem.Commun.
_journal_page_first              14742
_journal_paper_doi               10.1039/C5cc05095B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C44 H48 B2 F4 N4 S4'
_chemical_formula_sum            'C44 H48 B2 F4 N4 S4'
_chemical_formula_weight         858.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-01-23 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                94.761(7)
_cell_angle_beta                 96.451(7)
_cell_angle_gamma                101.646(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3989(2)
_cell_length_b                   14.2716(4)
_cell_length_c                   18.5507(13)
_cell_measurement_reflns_used    7649
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      2.4
_cell_volume                     2151.23(19)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector                 'Rapid II ccurved Image plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device
;
Crystal Goniometer ch-partial 
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_specimen_support Fiber
_diffrn_radiation_monochromator  'Confocal CMF Osmics'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.2743
_diffrn_reflns_laue_measured_fraction_full 0.969
_diffrn_reflns_laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17489
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        58.932
_diffrn_reflns_theta_max         58.932
_diffrn_reflns_theta_min         2.411
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    2.428
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, 1999'
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0876P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1979
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2390
_reflns_number_total             6004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05095b2.cif.txt
_cod_data_source_block           ec173a
_cod_original_cell_volume        2151.23(18)
_cod_database_code               7117827
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.642
_shelx_estimated_absorpt_t_max   0.642
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17746(18) 1.20015(9) 0.42458(8) 0.0519(5) Uani 1 1 d . . . . .
S2 S 0.72321(19) 0.35416(10) 0.09358(8) 0.0568(5) Uani 1 1 d . . . . .
S3 S -0.15232(19) 1.28146(10) 0.37432(8) 0.0565(5) Uani 1 1 d . . . . .
S4 S 1.0457(2) 0.26080(11) 0.13004(10) 0.0780(6) Uani 1 1 d . . . . .
F1 F 0.5699(4) 0.6035(2) 0.27290(17) 0.0699(10) Uani 1 1 d . . . . .
C44 C -1.0583(7) 1.5448(4) 0.2902(3) 0.081(2) Uani 1 1 d . . . . .
H44A H -1.1049 1.5262 0.3337 0.122 Uiso 1 1 calc R U . . .
H44B H -1.1459 1.5413 0.2506 0.122 Uiso 1 1 calc R U . . .
H44C H -0.9939 1.6102 0.2997 0.122 Uiso 1 1 calc R U . . .
C28 C 1.8949(8) -0.0565(5) 0.1756(4) 0.109(3) Uani 1 1 d . . . . .
H28A H 1.8278 -0.1177 0.1832 0.164 Uiso 1 1 calc R U . . .
H28B H 2.0022 -0.0478 0.2038 0.164 Uiso 1 1 calc R U . . .
H28C H 1.9068 -0.0556 0.1242 0.164 Uiso 1 1 calc R U . . .
F2 F 0.6763(4) 0.6873(2) 0.18624(17) 0.0717(11) Uani 1 1 d . . . . .
F4 F 0.2639(4) 0.9367(2) 0.28121(18) 0.0771(11) Uani 1 1 d . . . . .
N4 N 0.3812(6) 0.7987(3) 0.2626(3) 0.0463(13) Uani 1 1 d . . . . .
N3 N 0.5219(6) 0.9377(3) 0.3523(2) 0.0433(13) Uani 1 1 d . . . . .
N2 N 0.5238(6) 0.7623(3) 0.2657(2) 0.0447(13) Uani 1 1 d . . . . .
C19 C 0.9045(7) 0.2194(4) 0.0565(3) 0.0503(16) Uani 1 1 d . . . . .
N1 N 0.3846(6) 0.6274(3) 0.1700(2) 0.0452(13) Uani 1 1 d . . . . .
F3 F 0.2664(4) 0.8388(2) 0.37111(16) 0.0714(10) Uani 1 1 d . . . . .
C31 C 0.3639(6) 1.2132(4) 0.4803(3) 0.0413(15) Uani 1 1 d . . . . .
C14 C 0.4294(7) 0.4132(4) 0.0578(3) 0.0513(16) Uani 1 1 d . . . . .
H15 H 0.3277 0.4019 0.0281 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3444(8) 0.5475(4) 0.1193(3) 0.0491(17) Uani 1 1 d . . . . .
C34 C 0.1208(8) 1.2899(4) 0.4778(3) 0.0461(16) Uani 1 1 d . . . . .
C8 C 0.6612(8) 0.8988(4) 0.3512(3) 0.0444(16) Uani 1 1 d . . . . .
C1 C 0.2505(7) 0.6720(4) 0.1678(3) 0.0430(15) Uani 1 1 d . . . . .
C9 C 0.2561(7) 0.7532(4) 0.2152(3) 0.0464(17) Uani 1 1 d . . . . .
H20 H 0.1606 0.7783 0.2132 0.056 Uiso 1 1 calc R U . . .
C35 C -0.0357(7) 1.3183(3) 0.4580(3) 0.0460(16) Uani 1 1 d . . . . .
C10 C 0.6538(8) 0.8140(4) 0.3092(3) 0.0462(16) Uani 1 1 d . . . . .
H22 H 0.7504 0.7900 0.3114 0.055 Uiso 1 1 calc R U . . .
C2 C 0.1258(8) 0.6175(4) 0.1142(3) 0.0477(16) Uani 1 1 d . . . . .
C6 C 0.7340(7) 1.0343(3) 0.4258(3) 0.0433(15) Uani 1 1 d . . . . .
H24 H 0.7942 1.0863 0.4587 0.052 Uiso 1 1 calc R U . . .
C38 C -0.2957(7) 1.3474(4) 0.3939(4) 0.0498(17) Uani 1 1 d . . . . .
C33 C 0.2411(8) 1.3274(4) 0.5348(3) 0.0548(18) Uani 1 1 d . . . . .
H26 H 0.2325 1.3771 0.5697 0.066 Uiso 1 1 calc R U . . .
C16 C 0.5051(8) 0.2730(4) -0.0124(3) 0.0646(19) Uani 1 1 d . . . . .
H27 H 0.4094 0.2574 -0.0464 0.077 Uiso 1 1 calc R U . . .
C17 C 0.6312(8) 0.2225(4) -0.0124(3) 0.0619(19) Uani 1 1 d . . . . .
H17 H 0.6280 0.1698 -0.0468 0.074 Uiso 1 1 calc R U . . .
C11 C -0.0413(6) 0.6401(4) 0.0944(3) 0.0609(18) Uani 1 1 d . . . . .
H11A H -0.0406 0.6741 0.0512 0.091 Uiso 1 1 calc R U . . .
H11B H -0.0666 0.6801 0.1346 0.091 Uiso 1 1 calc R U . . .
H11C H -0.1236 0.5806 0.0847 0.091 Uiso 1 1 calc R U . . .
C30 C 0.4783(6) 1.1536(4) 0.4642(3) 0.0480(16) Uani 1 1 d . . . . .
H30 H 0.5827 1.1695 0.4919 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5352(7) 0.3479(4) 0.0424(3) 0.0453(15) Uani 1 1 d . . . . .
C5 C 0.5671(7) 1.0205(4) 0.3991(3) 0.0414(15) Uani 1 1 d . . . . .
C29 C 0.4495(7) 1.0788(3) 0.4140(3) 0.0497(16) Uani 1 1 d . . . . .
H33 H 0.3454 1.0621 0.3861 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9630(6) 0.9402(3) 0.4055(3) 0.0563(17) Uani 1 1 d . . . . .
H12A H 1.0364 0.9919 0.4377 0.084 Uiso 1 1 calc R U . . .
H12B H 1.0018 0.9357 0.3583 0.084 Uiso 1 1 calc R U . . .
H12C H 0.9603 0.8799 0.4264 0.084 Uiso 1 1 calc R U . . .
C39 C -0.4424(7) 1.3466(4) 0.3389(3) 0.0535(17) Uani 1 1 d . . . . .
H35A H -0.5094 1.2810 0.3302 0.064 Uiso 1 1 calc R U . . .
H35B H -0.4037 1.3632 0.2927 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7956(8) 0.9600(4) 0.3966(3) 0.0441(15) Uani 1 1 d . . . . .
C18 C 0.7593(9) 0.2559(4) 0.0415(3) 0.0520(17) Uani 1 1 d . . . . .
C20 C 0.9553(8) 0.1440(4) 0.0197(3) 0.056(2) Uani 1 1 d . . . . .
H38 H 0.8925 0.1076 -0.0222 0.067 Uiso 1 1 calc R U . . .
C41 C -0.6986(7) 1.4104(4) 0.3046(3) 0.0537(17) Uani 1 1 d . . . . .
H39A H -0.6613 1.4259 0.2580 0.064 Uiso 1 1 calc R U . . .
H39B H -0.7650 1.3447 0.2972 0.064 Uiso 1 1 calc R U . . .
C40 C -0.5497(7) 1.4143(4) 0.3606(3) 0.0559(17) Uani 1 1 d . . . . .
H40A H -0.4839 1.4802 0.3682 0.067 Uiso 1 1 calc R U . . .
H40B H -0.5872 1.3987 0.4071 0.067 Uiso 1 1 calc R U . . .
C13 C 0.4588(7) 0.4866(4) 0.1087(3) 0.0542(17) Uani 1 1 d . . . . .
H13 H 0.5592 0.4999 0.1395 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1848(8) 0.5421(4) 0.0851(3) 0.0541(17) Uani 1 1 d . . . . .
H42 H 0.1275 0.4944 0.0480 0.065 Uiso 1 1 calc R U . . .
C36 C -0.1038(7) 1.3793(4) 0.4984(3) 0.0590(18) Uani 1 1 d . . . . .
H36 H -0.0571 1.4080 0.5455 0.071 Uiso 1 1 calc R U . . .
C22 C 1.1676(8) 0.1807(5) 0.1093(4) 0.065(2) Uani 1 1 d . . . . .
C32 C 0.3785(7) 1.2850(4) 0.5366(3) 0.0559(17) Uani 1 1 d . . . . .
H46 H 0.4707 1.3038 0.5724 0.067 Uiso 1 1 calc R U . . .
C42 C -0.8047(7) 1.4788(4) 0.3267(3) 0.0588(18) Uani 1 1 d . . . . .
H47A H -0.7373 1.5442 0.3360 0.071 Uiso 1 1 calc R U . . .
H47B H -0.8459 1.4617 0.3723 0.071 Uiso 1 1 calc R U . . .
C23 C 1.3155(8) 0.1772(4) 0.1567(4) 0.085(2) Uani 1 1 d . . . . .
H48A H 1.2877 0.1712 0.2063 0.102 Uiso 1 1 calc R U . . .
H48B H 1.3936 0.2386 0.1580 0.102 Uiso 1 1 calc R U . . .
C43 C -0.9496(7) 1.4776(4) 0.2692(3) 0.0675(19) Uani 1 1 d . . . . .
H50A H -0.9079 1.4949 0.2238 0.081 Uiso 1 1 calc R U . . .
H50B H -1.0159 1.4119 0.2596 0.081 Uiso 1 1 calc R U . . .
C27 C 1.8152(9) 0.0226(5) 0.1993(4) 0.101(3) Uani 1 1 d . . . . .
H51A H 1.8862 0.0839 0.1925 0.121 Uiso 1 1 calc R U . . .
H51B H 1.8084 0.0222 0.2516 0.121 Uiso 1 1 calc R U . . .
C26 C 1.6436(9) 0.0192(5) 0.1601(4) 0.088(2) Uani 1 1 d . . . . .
H52A H 1.6512 0.0199 0.1078 0.106 Uiso 1 1 calc R U . . .
H52B H 1.5735 -0.0426 0.1664 0.106 Uiso 1 1 calc R U . . .
C25 C 1.5602(8) 0.0965(4) 0.1828(4) 0.088(2) Uani 1 1 d . . . . .
H53A H 1.6351 0.1587 0.1824 0.106 Uiso 1 1 calc R U . . .
H53B H 1.5380 0.0905 0.2331 0.106 Uiso 1 1 calc R U . . .
C21 C 1.0935(11) 0.1272(5) 0.0466(4) 0.089(3) Uani 1 1 d . . . . .
H55 H 1.1404 0.0801 0.0238 0.107 Uiso 1 1 calc R U . . .
C24 C 1.4006(8) 0.0965(4) 0.1357(3) 0.076(2) Uani 1 1 d . . . . .
H57A H 1.3249 0.0350 0.1374 0.091 Uiso 1 1 calc R U . . .
H57B H 1.4225 0.1001 0.0852 0.091 Uiso 1 1 calc R U . . .
C37 C -0.2530(8) 1.3956(4) 0.4625(3) 0.0617(19) Uani 1 1 d . . . . .
H37 H -0.3157 1.4353 0.4837 0.074 Uiso 1 1 calc R U . . .
B1 B 0.5421(11) 0.6664(5) 0.2220(4) 0.053(2) Uani 1 1 d . . . . .
B2 B 0.3522(10) 0.8814(5) 0.3190(4) 0.054(2) 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 0.0192 0.0096 '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 0.0098 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0755 0.0553 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0330 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3360 0.5651 '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
C34 S1 C31 92.2(3) . .
C15 S2 C18 92.6(3) . .
C35 S3 C38 92.8(3) . .
C19 S4 C22 94.1(4) . .
C43 C44 H44A 109.5 . .
C43 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
C43 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C9 N4 N2 117.1(5) . .
C9 N4 B2 117.8(5) . .
N2 N4 B2 124.5(5) . .
C5 N3 C8 106.4(5) . .
C5 N3 B2 130.1(5) . .
C8 N3 B2 122.2(5) . .
C10 N2 N4 116.4(5) . .
C10 N2 B1 118.2(5) . .
N4 N2 B1 125.4(6) . .
C20 C19 C18 130.0(6) . .
C20 C19 S4 106.7(5) . .
C18 C19 S4 123.2(5) . .
C4 N1 C1 108.1(5) . .
C4 N1 B1 129.6(5) . .
C1 N1 B1 122.3(5) . .
C32 C31 C30 129.0(5) . .
C32 C31 S1 110.2(4) . .
C30 C31 S1 120.8(4) . .
C13 C14 C15 127.5(6) . .
C13 C14 H15 116.2 . .
C15 C14 H15 116.2 . .
N1 C4 C3 107.8(5) . .
N1 C4 C13 121.1(6) . .
C3 C4 C13 131.1(6) . .
C33 C34 C35 128.9(5) . .
C33 C34 S1 110.5(5) . .
C35 C34 S1 120.6(5) . .
C10 C8 N3 120.1(6) . .
C10 C8 C7 130.0(6) . .
N3 C8 C7 109.9(5) . .
C9 C1 N1 120.2(6) . .
C9 C1 C2 132.0(6) . .
N1 C1 C2 107.7(5) . .
N4 C9 C1 126.6(6) . .
N4 C9 H20 116.7 . .
C1 C9 H20 116.7 . .
C36 C35 C34 126.9(6) . .
C36 C35 S3 110.6(5) . .
C34 C35 S3 122.3(4) . .
N2 C10 C8 126.5(6) . .
N2 C10 H22 116.8 . .
C8 C10 H22 116.8 . .
C3 C2 C1 107.2(6) . .
C3 C2 C11 127.6(6) . .
C1 C2 C11 125.2(5) . .
C7 C6 C5 109.4(5) . .
C7 C6 H24 125.3 . .
C5 C6 H24 125.3 . .
C37 C38 C39 129.1(5) . .
C37 C38 S3 110.2(5) . .
C39 C38 S3 120.7(4) . .
C34 C33 C32 114.2(5) . .
C34 C33 H26 122.9 . .
C32 C33 H26 122.9 . .
C15 C16 C17 113.1(6) . .
C15 C16 H27 123.4 . .
C17 C16 H27 123.4 . .
C18 C17 C16 114.6(6) . .
C18 C17 H17 122.7 . .
C16 C17 H17 122.7 . .
C2 C11 H11A 109.5 . .
C2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C29 C30 C31 125.9(5) . .
C29 C30 H30 117.0 . .
C31 C30 H30 117.0 . .
C16 C15 C14 127.0(6) . .
C16 C15 S2 110.0(4) . .
C14 C15 S2 123.0(4) . .
N3 C5 C6 109.0(5) . .
N3 C5 C29 121.0(6) . .
C6 C5 C29 130.1(5) . .
C30 C29 C5 124.6(6) . .
C30 C29 H33 117.7 . .
C5 C29 H33 117.7 . .
C7 C12 H12A 109.5 . .
C7 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C7 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C38 C39 C40 115.0(5) . .
C38 C39 H35A 108.5 . .
C40 C39 H35A 108.5 . .
C38 C39 H35B 108.5 . .
C40 C39 H35B 108.5 . .
H35A C39 H35B 107.5 . .
C6 C7 C8 105.4(5) . .
C6 C7 C12 131.5(6) . .
C8 C7 C12 123.1(5) . .
C17 C18 C19 128.0(6) . .
C17 C18 S2 109.7(5) . .
C19 C18 S2 122.3(5) . .
C21 C20 C19 115.9(7) . .
C21 C20 H38 122.0 . .
C19 C20 H38 122.0 . .
C42 C41 C40 113.4(5) . .
C42 C41 H39A 108.9 . .
C40 C41 H39A 108.9 . .
C42 C41 H39B 108.9 . .
C40 C41 H39B 108.9 . .
H39A C41 H39B 107.7 . .
C39 C40 C41 113.8(5) . .
C39 C40 H40A 108.8 . .
C41 C40 H40A 108.8 . .
C39 C40 H40B 108.8 . .
C41 C40 H40B 108.8 . .
H40A C40 H40B 107.7 . .
C14 C13 C4 123.0(6) . .
C14 C13 H13 118.5 . .
C4 C13 H13 118.5 . .
C2 C3 C4 109.1(6) . .
C2 C3 H42 125.4 . .
C4 C3 H42 125.4 . .
C35 C36 C37 113.4(6) . .
C35 C36 H36 123.3 . .
C37 C36 H36 123.3 . .
C21 C22 C23 131.5(7) . .
C21 C22 S4 106.7(6) . .
C23 C22 S4 121.8(6) . .
C31 C32 C33 112.9(5) . .
C31 C32 H46 123.6 . .
C33 C32 H46 123.6 . .
C41 C42 C43 113.2(5) . .
C41 C42 H47A 108.9 . .
C43 C42 H47A 108.9 . .
C41 C42 H47B 108.9 . .
C43 C42 H47B 108.9 . .
H47A C42 H47B 107.8 . .
C22 C23 C24 116.0(6) . .
C22 C23 H48A 108.3 . .
C24 C23 H48A 108.3 . .
C22 C23 H48B 108.3 . .
C24 C23 H48B 108.3 . .
H48A C23 H48B 107.4 . .
C44 C43 C42 114.2(5) . .
C44 C43 H50A 108.7 . .
C42 C43 H50A 108.7 . .
C44 C43 H50B 108.7 . .
C42 C43 H50B 108.7 . .
H50A C43 H50B 107.6 . .
C28 C27 C26 116.1(6) . .
C28 C27 H51A 108.3 . .
C26 C27 H51A 108.3 . .
C28 C27 H51B 108.3 . .
C26 C27 H51B 108.3 . .
H51A C27 H51B 107.4 . .
C25 C26 C27 117.5(6) . .
C25 C26 H52A 107.9 . .
C27 C26 H52A 107.9 . .
C25 C26 H52B 107.9 . .
C27 C26 H52B 107.9 . .
H52A C26 H52B 107.2 . .
C26 C25 C24 114.9(6) . .
C26 C25 H53A 108.5 . .
C24 C25 H53A 108.5 . .
C26 C25 H53B 108.5 . .
C24 C25 H53B 108.5 . .
H53A C25 H53B 107.5 . .
C20 C21 C22 116.5(7) . .
C20 C21 H55 121.8 . .
C22 C21 H55 121.8 . .
C25 C24 C23 115.8(6) . .
C25 C24 H57A 108.3 . .
C23 C24 H57A 108.3 . .
C25 C24 H57B 108.3 . .
C23 C24 H57B 108.3 . .
H57A C24 H57B 107.4 . .
C38 C37 C36 113.0(5) . .
C38 C37 H37 123.5 . .
C36 C37 H37 123.5 . .
F2 B1 F1 109.0(6) . .
F2 B1 N1 112.5(6) . .
F1 B1 N1 112.1(6) . .
F2 B1 N2 107.9(5) . .
F1 B1 N2 107.1(5) . .
N1 B1 N2 108.0(5) . .
F4 B2 F3 110.9(6) . .
F4 B2 N3 112.3(6) . .
F3 B2 N3 111.4(6) . .
F4 B2 N4 107.7(6) . .
F3 B2 N4 108.2(5) . .
N3 B2 N4 106.0(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C34 1.727(5) .
S1 C31 1.744(5) .
S2 C15 1.731(5) .
S2 C18 1.733(5) .
S3 C35 1.721(6) .
S3 C38 1.723(5) .
S4 C19 1.685(6) .
S4 C22 1.730(6) .
F1 B1 1.388(7) .
C44 C43 1.510(6) .
C44 H44A 0.9700 .
C44 H44B 0.9700 .
C44 H44C 0.9700 .
C28 C27 1.485(7) .
C28 H28A 0.9700 .
C28 H28B 0.9700 .
C28 H28C 0.9700 .
F2 B1 1.365(7) .
F4 B2 1.370(7) .
N4 C9 1.312(6) .
N4 N2 1.396(5) .
N4 B2 1.586(7) .
N3 C5 1.367(6) .
N3 C8 1.394(6) .
N3 B2 1.522(8) .
N2 C10 1.329(6) .
N2 B1 1.576(7) .
C19 C20 1.391(6) .
C19 C18 1.429(7) .
N1 C4 1.376(6) .
N1 C1 1.400(6) .
N1 B1 1.522(8) .
F3 B2 1.378(7) .
C31 C32 1.379(6) .
C31 C30 1.445(6) .
C14 C13 1.314(6) .
C14 C15 1.445(6) .
C14 H15 0.9400 .
C4 C3 1.402(7) .
C4 C13 1.438(7) .
C34 C33 1.367(6) .
C34 C35 1.470(7) .
C8 C10 1.371(7) .
C8 C7 1.419(7) .
C1 C9 1.385(7) .
C1 C2 1.414(7) .
C9 H20 0.9400 .
C35 C36 1.354(6) .
C10 H22 0.9400 .
C2 C3 1.369(6) .
C2 C11 1.515(6) .
C6 C7 1.369(6) .
C6 C5 1.403(6) .
C6 H24 0.9400 .
C38 C37 1.369(7) .
C38 C39 1.506(6) .
C33 C32 1.405(6) .
C33 H26 0.9400 .
C16 C15 1.376(6) .
C16 C17 1.396(6) .
C16 H27 0.9400 .
C17 C18 1.363(7) .
C17 H17 0.9400 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 H11C 0.9700 .
C30 C29 1.321(6) .
C30 H30 0.9400 .
C5 C29 1.448(6) .
C29 H33 0.9400 .
C12 C7 1.484(6) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 H12C 0.9700 .
C39 C40 1.509(6) .
C39 H35A 0.9800 .
C39 H35B 0.9800 .
C20 C21 1.287(8) .
C20 H38 0.9400 .
C41 C42 1.509(6) .
C41 C40 1.521(6) .
C41 H39A 0.9800 .
C41 H39B 0.9800 .
C40 H40A 0.9800 .
C40 H40B 0.9800 .
C13 H13 0.9400 .
C3 H42 0.9400 .
C36 C37 1.422(6) .
C36 H36 0.9400 .
C22 C21 1.349(8) .
C22 C23 1.451(7) .
C32 H46 0.9400 .
C42 C43 1.521(6) .
C42 H47A 0.9800 .
C42 H47B 0.9800 .
C23 C24 1.519(7) .
C23 H48A 0.9800 .
C23 H48B 0.9800 .
C43 H50A 0.9800 .
C43 H50B 0.9800 .
C27 C26 1.529(7) .
C27 H51A 0.9800 .
C27 H51B 0.9800 .
C26 C25 1.478(7) .
C26 H52A 0.9800 .
C26 H52B 0.9800 .
C25 C24 1.515(7) .
C25 H53A 0.9800 .
C25 H53B 0.9800 .
C21 H55 0.9400 .
C24 H57A 0.9800 .
C24 H57B 0.9800 .
C37 H37 0.9400 .
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
C9 N4 N2 C10 174.2(4) . . . .
B2 N4 N2 C10 -14.6(7) . . . .
C9 N4 N2 B1 -5.6(7) . . . .
B2 N4 N2 B1 165.7(5) . . . .
C22 S4 C19 C20 1.2(4) . . . .
C22 S4 C19 C18 178.2(5) . . . .
C34 S1 C31 C32 -0.6(4) . . . .
C34 S1 C31 C30 179.8(4) . . . .
C1 N1 C4 C3 0.2(6) . . . .
B1 N1 C4 C3 179.9(5) . . . .
C1 N1 C4 C13 179.8(4) . . . .
B1 N1 C4 C13 -0.4(8) . . . .
C31 S1 C34 C33 0.4(4) . . . .
C31 S1 C34 C35 178.6(4) . . . .
C5 N3 C8 C10 179.3(4) . . . .
B2 N3 C8 C10 11.1(8) . . . .
C5 N3 C8 C7 -1.6(6) . . . .
B2 N3 C8 C7 -169.9(5) . . . .
C4 N1 C1 C9 178.1(5) . . . .
B1 N1 C1 C9 -1.7(7) . . . .
C4 N1 C1 C2 -0.1(6) . . . .
B1 N1 C1 C2 -179.8(5) . . . .
N2 N4 C9 C1 0.3(8) . . . .
B2 N4 C9 C1 -171.5(5) . . . .
N1 C1 C9 N4 3.3(8) . . . .
C2 C1 C9 N4 -179.1(5) . . . .
C33 C34 C35 C36 -10.1(9) . . . .
S1 C34 C35 C36 172.2(4) . . . .
C33 C34 C35 S3 165.7(5) . . . .
S1 C34 C35 S3 -12.0(6) . . . .
C38 S3 C35 C36 -0.6(4) . . . .
C38 S3 C35 C34 -177.1(4) . . . .
N4 N2 C10 C8 0.2(8) . . . .
B1 N2 C10 C8 -180.0(5) . . . .
N3 C8 C10 N2 1.6(8) . . . .
C7 C8 C10 N2 -177.2(5) . . . .
C9 C1 C2 C3 -177.9(5) . . . .
N1 C1 C2 C3 -0.1(6) . . . .
C9 C1 C2 C11 1.7(9) . . . .
N1 C1 C2 C11 179.6(4) . . . .
C35 S3 C38 C37 0.1(4) . . . .
C35 S3 C38 C39 -179.9(4) . . . .
C35 C34 C33 C32 -178.1(5) . . . .
S1 C34 C33 C32 -0.1(6) . . . .
C15 C16 C17 C18 0.4(7) . . . .
C32 C31 C30 C29 172.0(5) . . . .
S1 C31 C30 C29 -8.5(7) . . . .
C17 C16 C15 C14 -179.4(5) . . . .
C17 C16 C15 S2 0.1(6) . . . .
C13 C14 C15 C16 -177.9(5) . . . .
C13 C14 C15 S2 2.7(8) . . . .
C18 S2 C15 C16 -0.4(4) . . . .
C18 S2 C15 C14 179.1(4) . . . .
C8 N3 C5 C6 1.2(5) . . . .
B2 N3 C5 C6 168.2(5) . . . .
C8 N3 C5 C29 -178.9(4) . . . .
B2 N3 C5 C29 -11.9(8) . . . .
C7 C6 C5 N3 -0.4(6) . . . .
C7 C6 C5 C29 179.7(5) . . . .
C31 C30 C29 C5 179.8(4) . . . .
N3 C5 C29 C30 172.3(5) . . . .
C6 C5 C29 C30 -7.8(9) . . . .
C37 C38 C39 C40 5.2(8) . . . .
S3 C38 C39 C40 -174.8(4) . . . .
C5 C6 C7 C8 -0.6(6) . . . .
C5 C6 C7 C12 179.0(5) . . . .
C10 C8 C7 C6 -179.7(5) . . . .
N3 C8 C7 C6 1.4(6) . . . .
C10 C8 C7 C12 0.7(9) . . . .
N3 C8 C7 C12 -178.3(4) . . . .
C16 C17 C18 C19 179.1(5) . . . .
C16 C17 C18 S2 -0.6(7) . . . .
C20 C19 C18 C17 2.3(10) . . . .
S4 C19 C18 C17 -173.9(5) . . . .
C20 C19 C18 S2 -177.9(5) . . . .
S4 C19 C18 S2 5.8(7) . . . .
C15 S2 C18 C17 0.6(4) . . . .
C15 S2 C18 C19 -179.2(4) . . . .
C18 C19 C20 C21 -179.7(6) . . . .
S4 C19 C20 C21 -2.9(7) . . . .
C38 C39 C40 C41 -178.9(4) . . . .
C42 C41 C40 C39 -179.7(4) . . . .
C15 C14 C13 C4 179.9(5) . . . .
N1 C4 C13 C14 -175.6(5) . . . .
C3 C4 C13 C14 3.9(9) . . . .
C1 C2 C3 C4 0.2(6) . . . .
C11 C2 C3 C4 -179.4(5) . . . .
N1 C4 C3 C2 -0.3(6) . . . .
C13 C4 C3 C2 -179.9(5) . . . .
C34 C35 C36 C37 177.3(5) . . . .
S3 C35 C36 C37 1.0(6) . . . .
C19 S4 C22 C21 0.6(5) . . . .
C19 S4 C22 C23 -177.5(5) . . . .
C30 C31 C32 C33 -179.8(5) . . . .
S1 C31 C32 C33 0.7(5) . . . .
C34 C33 C32 C31 -0.3(7) . . . .
C40 C41 C42 C43 177.7(4) . . . .
C21 C22 C23 C24 -3.6(10) . . . .
S4 C22 C23 C24 173.9(4) . . . .
C41 C42 C43 C44 179.6(4) . . . .
C28 C27 C26 C25 179.5(5) . . . .
C27 C26 C25 C24 172.5(5) . . . .
C19 C20 C21 C22 3.7(9) . . . .
C23 C22 C21 C20 175.3(6) . . . .
S4 C22 C21 C20 -2.5(8) . . . .
C26 C25 C24 C23 -178.2(5) . . . .
C22 C23 C24 C25 176.6(5) . . . .
C39 C38 C37 C36 -179.5(5) . . . .
S3 C38 C37 C36 0.5(6) . . . .
C35 C36 C37 C38 -1.0(7) . . . .
C4 N1 B1 F2 58.7(7) . . . .
C1 N1 B1 F2 -121.6(5) . . . .
C4 N1 B1 F1 -64.5(7) . . . .
C1 N1 B1 F1 115.2(5) . . . .
C4 N1 B1 N2 177.7(4) . . . .
C1 N1 B1 N2 -2.6(7) . . . .
C10 N2 B1 F2 -51.5(7) . . . .
N4 N2 B1 F2 128.2(6) . . . .
C10 N2 B1 F1 65.7(7) . . . .
N4 N2 B1 F1 -114.6(6) . . . .
C10 N2 B1 N1 -173.4(4) . . . .
N4 N2 B1 N1 6.4(7) . . . .
C5 N3 B2 F4 56.5(8) . . . .
C8 N3 B2 F4 -138.3(5) . . . .
C5 N3 B2 F3 -68.7(7) . . . .
C8 N3 B2 F3 96.6(6) . . . .
C5 N3 B2 N4 173.8(5) . . . .
C8 N3 B2 N4 -20.9(7) . . . .
C9 N4 B2 F4 -44.9(7) . . . .
N2 N4 B2 F4 143.9(5) . . . .
C9 N4 B2 F3 75.0(7) . . . .
N2 N4 B2 F3 -96.1(7) . . . .
C9 N4 B2 N3 -165.3(5) . . . .
N2 N4 B2 N3 23.5(7) . . . .
