#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:41:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180311 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/25/7152564.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_7152564
loop_
_publ_author_name
'Nakamura, Mitsunori'
'Tahara, Hiroyuki'
'Takahashi, Kohtaro'
'Nagata, Toshi'
'Uoyama, Hiroki'
'Kuzuhara, Daiki'
'Mori, Shigeki'
'Okujima, Tetsuo'
'Yamada, Hiroko'
'Uno, Hidemitsu'
_publ_section_title
;
 π-Fused bis-BODIPY as a candidate for NIR dyes.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6840
_journal_page_last               6849
_journal_paper_doi               10.1039/c2ob25930c
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C32 H36 B2 F4 N4, 2(C10 H7 Cl)'
_chemical_formula_sum            'C52 H50 B2 Cl2 F4 N4'
_chemical_formula_weight         899.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                98.902(13)
_cell_angle_beta                 93.514(13)
_cell_angle_gamma                104.888(14)
_cell_formula_units_Z            1
_cell_length_a                   7.944(3)
_cell_length_b                   10.964(4)
_cell_length_c                   13.432(4)
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      1.95
_cell_volume                     1110.7(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.1016
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12159
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             470.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.750
_refine_ls_extinction_coef       0.042(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.233
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.233
_refine_ls_R_factor_all          0.1916
_refine_ls_R_factor_gt           0.1653
_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)+(0.0000P)²+17.4958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3905
_refine_ls_wR_factor_ref         0.3974
_reflns_number_gt                3071
_reflns_number_total             5031
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c2ob25930c.txt
_cod_data_source_block           tahara
_cod_database_code               7152564
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.6912(5) 0.3191(5) 0.6392(3) 0.0838(14) Uani 1.0 2 d .
F1 F 0.4567(6) 0.1987(4) -0.0698(4) 0.0224(11) Uani 1.0 2 d .
F2 F 0.3168(6) 0.1194(4) 0.0609(4) 0.0239(11) Uani 1.0 2 d .
N1 N 0.5620(9) 0.3103(6) 0.1020(5) 0.0187(14) Uani 1.0 2 d .
N2 N 0.2746(8) 0.3163(6) 0.0179(5) 0.0176(13) Uani 1.0 2 d .
C1 C 0.7049(10) 0.2736(7) 0.1338(6) 0.0189(15) Uani 1.0 2 d .
C2 C 0.8211(11) 0.3752(8) 0.2008(6) 0.0218(16) Uani 1.0 2 d .
C3 C 0.7496(10) 0.4794(7) 0.2097(6) 0.0184(15) Uani 1.0 2 d .
C4 C 0.5868(10) 0.4385(7) 0.1483(6) 0.0187(15) Uani 1.0 2 d .
C5 C 0.4605(10) 0.5026(7) 0.1306(6) 0.0182(15) Uani 1.0 2 d .
C6 C 0.3089(10) 0.4444(7) 0.0685(6) 0.0186(15) Uani 1.0 2 d .
C7 C 0.1594(10) 0.4904(7) 0.0400(6) 0.0180(15) Uani 1.0 2 d .
C8 C 0.0371(10) 0.3844(7) -0.0262(6) 0.0175(15) Uani 1.0 2 d .
C9 C 0.1191(10) 0.2803(7) -0.0370(6) 0.0197(16) Uani 1.0 2 d .
C10 C 0.1231(10) 0.6072(7) 0.0670(6) 0.0174(15) Uani 1.0 2 d .
C11 C 0.7207(11) 0.1408(7) 0.0990(7) 0.0246(18) Uani 1.0 2 d .
C12 C 0.9981(11) 0.3718(8) 0.2495(6) 0.0250(17) Uani 1.0 2 d .
C13 C 0.9908(15) 0.3276(12) 0.3504(7) 0.046(3) Uani 1.0 2 d .
C14 C 0.8221(12) 0.6112(8) 0.2740(7) 0.0268(18) Uani 1.0 2 d .
C15 C 0.7986(17) 0.6181(10) 0.3836(7) 0.045(3) Uani 1.0 2 d .
C16 C 0.0441(11) 0.1488(7) -0.0988(7) 0.0238(17) Uani 1.0 2 d .
C17 C 0.5019(13) 0.1873(10) 0.6015(8) 0.042(3) Uani 1.0 2 d .
C18 C 0.4331(16) 0.1155(12) 0.6741(8) 0.051(4) Uani 1.0 2 d .
C19 C 0.2940(17) 0.0155(12) 0.6416(9) 0.051(3) Uani 1.0 2 d .
C20 C 0.2211(15) -0.0169(10) 0.5438(8) 0.042(3) Uani 1.0 2 d .
C21 C 0.2858(13) 0.0568(9) 0.4694(7) 0.033(2) Uani 1.0 2 d .
C22 C 0.2046(14) 0.0277(10) 0.3678(7) 0.037(3) Uani 1.0 2 d .
C23 C 0.2695(15) 0.0999(11) 0.2983(8) 0.044(3) Uani 1.0 2 d .
C24 C 0.4137(15) 0.2079(11) 0.3262(9) 0.046(3) Uani 1.0 2 d .
C25 C 0.4938(15) 0.2399(11) 0.4242(9) 0.045(3) Uani 1.0 2 d .
C26 C 0.4301(13) 0.1627(10) 0.4986(7) 0.036(3) Uani 1.0 2 d .
B1 B 0.4060(12) 0.2317(8) 0.0272(6) 0.0171(17) Uani 1.0 2 d .
H5 H 0.4803 0.5894 0.1626 0.0218 Uiso 1.0 2 calc R
H10 H 0.2031 0.6773 0.1107 0.0209 Uiso 1.0 2 calc R
H11A H 0.6282 0.0788 0.1242 0.0295 Uiso 1.0 2 calc R
H11B H 0.8355 0.1346 0.1253 0.0295 Uiso 1.0 2 calc R
H11C H 0.7087 0.1220 0.0248 0.0295 Uiso 1.0 2 calc R
H12A H 1.0465 0.3139 0.2026 0.0300 Uiso 1.0 2 calc R
H12B H 1.0796 0.4588 0.2588 0.0300 Uiso 1.0 2 calc R
H13A H 0.9352 0.3804 0.3961 0.0685 Uiso 1.0 2 calc R
H13B H 1.1099 0.3361 0.3801 0.0685 Uiso 1.0 2 calc R
H13C H 0.9225 0.2377 0.3408 0.0685 Uiso 1.0 2 calc R
H14A H 0.9488 0.6410 0.2671 0.0322 Uiso 1.0 2 calc R
H14B H 0.7646 0.6712 0.2470 0.0322 Uiso 1.0 2 calc R
H15A H 0.6745 0.5830 0.3914 0.0676 Uiso 1.0 2 calc R
H15B H 0.8379 0.7077 0.4181 0.0676 Uiso 1.0 2 calc R
H15C H 0.8678 0.5681 0.4135 0.0676 Uiso 1.0 2 calc R
H16A H 0.1296 0.1278 -0.1434 0.0286 Uiso 1.0 2 calc R
H16B H -0.0633 0.1467 -0.1398 0.0286 Uiso 1.0 2 calc R
H16C H 0.0170 0.0860 -0.0535 0.0286 Uiso 1.0 2 calc R
H18 H 0.4825 0.1366 0.7428 0.0614 Uiso 1.0 2 calc R
H19 H 0.2438 -0.0353 0.6890 0.0618 Uiso 1.0 2 calc R
H20 H 0.1244 -0.0906 0.5248 0.0505 Uiso 1.0 2 calc R
H22 H 0.1038 -0.0431 0.3485 0.0450 Uiso 1.0 2 calc R
H23 H 0.2168 0.0771 0.2303 0.0524 Uiso 1.0 2 calc R
H24 H 0.4562 0.2591 0.2774 0.0547 Uiso 1.0 2 calc R
H25 H 0.5914 0.3131 0.4427 0.0539 Uiso 1.0 2 calc R
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C4 107.2(6) yes . .
C1 N1 B1 127.7(7) yes . .
C4 N1 B1 125.0(7) yes . .
C6 N2 C9 110.3(7) yes . .
C6 N2 B1 123.3(6) yes . .
C9 N2 B1 126.4(6) yes . .
N1 C1 C2 109.9(7) yes . .
N1 C1 C11 121.3(6) yes . .
C2 C1 C11 128.8(8) yes . .
C1 C2 C3 107.7(7) yes . .
C1 C2 C12 125.1(8) yes . .
C3 C2 C12 127.2(7) yes . .
C2 C3 C4 106.9(6) yes . .
C2 C3 C14 128.6(7) yes . .
C4 C3 C14 124.5(8) yes . .
N1 C4 C3 108.3(7) yes . .
N1 C4 C5 120.5(6) yes . .
C3 C4 C5 131.2(7) yes . .
C4 C5 C6 122.0(7) yes . .
N2 C6 C5 121.2(8) yes . .
N2 C6 C7 107.1(6) yes . .
C5 C6 C7 131.8(7) yes . .
C6 C7 C8 106.4(7) yes . .
C6 C7 C10 131.9(6) yes . .
C8 C7 C10 121.7(8) yes . .
C7 C8 C9 106.0(7) yes . .
C7 C8 C10 122.5(7) yes . 2_565
C9 C8 C10 131.5(6) yes . 2_565
N2 C9 C8 110.2(6) yes . .
N2 C9 C16 123.2(8) yes . .
C8 C9 C16 126.6(7) yes . .
C7 C10 C8 115.8(6) yes . 2_565
C2 C12 C13 114.1(8) yes . .
C3 C14 C15 114.9(8) yes . .
Cl1 C17 C18 118.6(8) yes . .
Cl1 C17 C26 117.2(8) yes . .
C18 C17 C26 124.3(9) yes . .
C17 C18 C19 116.3(10) yes . .
C18 C19 C20 123.0(12) yes . .
C19 C20 C21 121.6(9) yes . .
C20 C21 C22 122.1(8) yes . .
C20 C21 C26 118.2(9) yes . .
C22 C21 C26 119.7(9) yes . .
C21 C22 C23 120.7(9) yes . .
C22 C23 C24 120.6(9) yes . .
C23 C24 C25 120.2(11) yes . .
C24 C25 C26 120.2(9) yes . .
C17 C26 C21 116.5(9) yes . .
C17 C26 C25 124.9(9) yes . .
C21 C26 C25 118.5(9) yes . .
F1 B1 F2 109.4(6) yes . .
F1 B1 N1 111.6(7) yes . .
F1 B1 N2 108.0(7) yes . .
F2 B1 N1 111.8(7) yes . .
F2 B1 N2 108.0(7) yes . .
N1 B1 N2 107.9(6) yes . .
C4 C5 H5 119.013 no . .
C6 C5 H5 119.008 no . .
C7 C10 H10 122.094 no . .
C8 C10 H10 122.098 no 2_565 .
C1 C11 H11A 109.476 no . .
C1 C11 H11B 109.471 no . .
C1 C11 H11C 109.472 no . .
H11A C11 H11B 109.467 no . .
H11A C11 H11C 109.467 no . .
H11B C11 H11C 109.474 no . .
C2 C12 H12A 108.728 no . .
C2 C12 H12B 108.730 no . .
C13 C12 H12A 108.720 no . .
C13 C12 H12B 108.722 no . .
H12A C12 H12B 107.637 no . .
C12 C13 H13A 109.473 no . .
C12 C13 H13B 109.473 no . .
C12 C13 H13C 109.477 no . .
H13A C13 H13B 109.471 no . .
H13A C13 H13C 109.468 no . .
H13B C13 H13C 109.466 no . .
C3 C14 H14A 108.539 no . .
C3 C14 H14B 108.540 no . .
C15 C14 H14A 108.545 no . .
C15 C14 H14B 108.540 no . .
H14A C14 H14B 107.532 no . .
C14 C15 H15A 109.468 no . .
C14 C15 H15B 109.473 no . .
C14 C15 H15C 109.471 no . .
H15A C15 H15B 109.474 no . .
H15A C15 H15C 109.471 no . .
H15B C15 H15C 109.470 no . .
C9 C16 H16A 109.467 no . .
C9 C16 H16B 109.472 no . .
C9 C16 H16C 109.473 no . .
H16A C16 H16B 109.476 no . .
H16A C16 H16C 109.471 no . .
H16B C16 H16C 109.468 no . .
C17 C18 H18 121.830 no . .
C19 C18 H18 121.834 no . .
C18 C19 H19 118.497 no . .
C20 C19 H19 118.498 no . .
C19 C20 H20 119.187 no . .
C21 C20 H20 119.190 no . .
C21 C22 H22 119.625 no . .
C23 C22 H22 119.632 no . .
C22 C23 H23 119.713 no . .
C24 C23 H23 119.709 no . .
C23 C24 H24 119.920 no . .
C25 C24 H24 119.919 no . .
C24 C25 H25 119.878 no . .
C26 C25 H25 119.873 no . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Cl1 C17 1.780(10) yes .
F1 B1 1.408(10) yes .
F2 B1 1.409(9) yes .
N1 C1 1.364(11) yes .
N1 C4 1.406(10) yes .
N1 B1 1.522(10) yes .
N2 C6 1.412(9) yes .
N2 C9 1.331(10) yes .
N2 B1 1.576(12) yes .
C1 C2 1.401(9) yes .
C1 C11 1.499(12) yes .
C2 C3 1.393(13) yes .
C2 C12 1.525(13) yes .
C3 C4 1.418(10) yes .
C3 C14 1.514(10) yes .
C4 C5 1.393(12) yes .
C5 C6 1.368(10) yes .
C6 C7 1.457(12) yes .
C7 C8 1.442(9) yes .
C7 C10 1.383(12) yes .
C8 C9 1.446(12) yes .
C8 C10 1.385(11) yes 2_565
C9 C16 1.500(10) yes .
C12 C13 1.508(14) yes .
C14 C15 1.488(13) yes .
C17 C18 1.397(17) yes .
C17 C26 1.421(14) yes .
C18 C19 1.336(15) yes .
C19 C20 1.357(15) yes .
C20 C21 1.419(15) yes .
C21 C22 1.426(13) yes .
C21 C26 1.392(12) yes .
C22 C23 1.356(15) yes .
C23 C24 1.403(14) yes .
C24 C25 1.378(16) yes .
C25 C26 1.440(16) yes .
C5 H5 0.950 no .
C10 H10 0.950 no .
C11 H11A 0.980 no .
C11 H11B 0.980 no .
C11 H11C 0.980 no .
C12 H12A 0.990 no .
C12 H12B 0.990 no .
C13 H13A 0.980 no .
C13 H13B 0.980 no .
C13 H13C 0.980 no .
C14 H14A 0.990 no .
C14 H14B 0.990 no .
C15 H15A 0.980 no .
C15 H15B 0.980 no .
C15 H15C 0.980 no .
C16 H16A 0.980 no .
C16 H16B 0.980 no .
C16 H16C 0.980 no .
C18 H18 0.950 no .
C19 H19 0.950 no .
C20 H20 0.950 no .
C22 H22 0.950 no .
C23 H23 0.950 no .
C24 H24 0.950 no .
C25 H25 0.950 no .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_2
Cl1 C25 3.085(12) no .
F1 C1 3.139(9) no .
F1 C4 3.523(8) no .
F1 C6 3.525(9) no .
F1 C9 3.072(10) no .
F1 C11 3.239(10) no .
F1 C16 3.170(10) no .
F2 C1 3.124(9) no .
F2 C4 3.575(8) no .
F2 C6 3.565(9) no .
F2 C9 3.032(10) no .
F2 C11 3.160(10) no .
F2 C16 3.066(10) no .
N1 C6 2.832(12) no .
N2 C4 2.837(9) no .
C1 C5 3.550(13) no .
C1 C13 3.455(13) no .
C2 C15 3.380(13) no .
C3 C13 3.490(16) no .
C4 C15 3.523(11) no .
C5 C9 3.539(9) no .
C5 C10 3.291(12) no .
C5 C14 3.198(11) no .
C5 B1 2.988(11) no .
C7 C7 2.761(12) no 2_565
C8 C8 2.745(11) no 2_565
C10 C10 2.913(9) no 2_565
C10 C16 3.263(12) no 2_565
C11 C12 3.219(10) no .
C11 B1 3.075(14) no .
C12 C14 3.260(14) no .
C16 B1 3.088(12) no .
C17 C20 2.697(13) no .
C18 C21 2.830(14) no .
C19 C26 2.789(16) no .
C21 C24 2.800(16) no .
C22 C25 2.786(14) no .
C23 C26 2.809(14) no .
F1 C5 3.407(9) no 2_665
F1 C10 3.462(8) no 2_665
F1 C11 3.575(9) no 2_655
F1 C18 3.401(11) no 1_554
F2 C11 3.229(9) no 2_655
F2 C23 3.268(12) no .
F2 C24 3.528(12) no .
N1 C7 3.555(10) no 2_665
N1 C10 3.520(10) no 2_665
N1 C24 3.539(14) no .
N2 C5 3.455(10) no 2_665
C1 C8 3.594(11) no 1_655
C1 C10 3.387(11) no 2_665
C2 C8 3.592(11) no 1_655
C3 C7 3.522(11) no 2_665
C3 C8 3.395(11) no 2_665
C4 C6 3.424(11) no 2_665
C4 C7 3.391(11) no 2_665
C5 F1 3.407(9) no 2_665
C5 N2 3.455(10) no 2_665
C5 C5 3.596(11) no 2_665
C5 C6 3.373(11) no 2_665
C6 C4 3.424(11) no 2_665
C6 C5 3.373(11) no 2_665
C7 N1 3.555(10) no 2_665
C7 C3 3.522(11) no 2_665
C7 C4 3.391(11) no 2_665
C7 C12 3.459(12) no 1_455
C8 C1 3.594(11) no 1_455
C8 C2 3.592(11) no 1_455
C8 C3 3.395(11) no 2_665
C8 C14 3.578(12) no 2_665
C9 C14 3.583(12) no 2_665
C10 F1 3.462(8) no 2_665
C10 N1 3.520(10) no 2_665
C10 C1 3.387(11) no 2_665
C11 F1 3.575(9) no 2_655
C11 F2 3.229(9) no 2_655
C12 C7 3.459(12) no 1_655
C14 C8 3.578(12) no 2_665
C14 C9 3.583(12) no 2_665
C15 C17 3.582(18) no 2_666
C17 C15 3.582(18) no 2_666
C17 C21 3.556(16) no 2_656
C18 F1 3.401(11) no 1_556
C20 C26 3.571(17) no 2_656
C21 C17 3.556(16) no 2_656
C23 F2 3.268(12) no .
C24 F2 3.528(12) no .
C24 N1 3.539(14) no .
C26 C20 3.571(17) no 2_656
Cl1 H18 2.8510 no .
Cl1 H25 2.6941 no .
F1 H11A 3.4523 no .
F1 H11C 2.6857 no .
F1 H16A 2.5965 no .
F1 H16C 3.4252 no .
F2 H11A 2.7324 no .
F2 H11C 3.1737 no .
F2 H16A 3.0653 no .
F2 H16C 2.6634 no .
N1 H5 3.2808 no .
N1 H11A 2.7758 no .
N1 H11B 3.2835 no .
N1 H11C 2.7229 no .
N2 H5 3.2726 no .
N2 H16A 2.7153 no .
N2 H16B 3.2659 no .
N2 H16C 2.7994 no .
C1 H12A 2.7130 no .
C1 H12B 3.3204 no .
C1 H13C 3.3124 no .
C2 H11A 3.1910 no .
C2 H11B 2.7102 no .
C2 H11C 3.2454 no .
C2 H13A 2.7084 no .
C2 H13B 3.3756 no .
C2 H13C 2.7880 no .
C2 H14A 2.8073 no .
C2 H14B 3.3579 no .
C2 H15C 3.2200 no .
C3 H5 2.7975 no .
C3 H12A 3.3221 no .
C3 H12B 2.7376 no .
C3 H13A 3.2898 no .
C3 H15A 2.6962 no .
C3 H15B 3.3584 no .
C3 H15C 2.7772 no .
C4 H14A 3.2868 no .
C4 H14B 2.6701 no .
C4 H15A 3.3478 no .
C5 H10 3.1662 no .
C5 H14B 2.8356 no .
C6 H10 2.8740 no .
C7 H5 2.8108 no .
C7 H10 3.3439 no 2_565
C8 H10 3.3359 no .
C8 H16A 3.2806 no .
C8 H16B 2.7033 no .
C8 H16C 3.1968 no .
C9 H10 2.8621 no 2_565
C10 H5 3.1076 no .
C10 H16B 2.8918 no 2_565
C11 H12A 2.9072 no .
C11 H13C 3.4153 no .
C12 H11B 2.8077 no .
C12 H14A 3.0517 no .
C12 H15C 3.2424 no .
C13 H11B 3.3714 no .
C13 H15C 3.0591 no .
C14 H5 2.9531 no .
C14 H12B 2.9534 no .
C14 H13A 3.4887 no .
C15 H12B 3.5211 no .
C15 H13A 3.0922 no .
C16 H10 3.0819 no 2_565
C17 H19 3.1867 no .
C17 H25 2.7476 no .
C18 H20 3.2079 no .
C20 H18 3.2278 no .
C20 H22 2.6768 no .
C21 H19 3.2711 no .
C21 H23 3.2768 no .
C21 H25 3.2916 no .
C22 H20 2.6685 no .
C22 H24 3.2487 no .
C23 H25 3.2687 no .
C24 H22 3.2536 no .
C25 H23 3.2640 no .
C26 H18 3.3466 no .
C26 H20 3.2677 no .
C26 H22 3.2893 no .
C26 H24 3.3045 no .
B1 H11A 3.0879 no .
B1 H11C 2.9516 no .
B1 H16A 2.9425 no .
B1 H16C 3.1289 no .
H5 H10 2.7160 no .
H5 H14B 2.3488 no .
H5 H15A 3.3713 no .
H10 H16B 2.4561 no 2_565
H11A H13C 3.5312 no .
H11B H12A 2.2832 no .
H11B H13C 2.9108 no .
H11C H12A 3.4765 no .
H12A H13A 2.8451 no .
H12A H13B 2.3684 no .
H12A H13C 2.3228 no .
H12B H13A 2.3863 no .
H12B H13B 2.3065 no .
H12B H13C 2.8435 no .
H12B H14A 2.4692 no .
H12B H15C 3.0459 no .
H13A H14A 3.5457 no .
H13A H15A 3.4083 no .
H13A H15C 2.2378 no .
H13B H15C 3.5555 no .
H14A H15A 2.8283 no .
H14A H15B 2.3476 no .
H14A H15C 2.3017 no .
H14B H15A 2.3674 no .
H14B H15B 2.2834 no .
H14B H15C 2.8265 no .
H18 H19 2.2902 no .
H19 H20 2.2736 no .
H20 H22 2.5066 no .
H22 H23 2.2973 no .
H23 H24 2.3479 no .
H24 H25 2.3253 no .
Cl1 H5 3.2046 no 2_666
Cl1 H10 3.4045 no 2_666
Cl1 H12B 2.7401 no 2_766
Cl1 H14A 2.9501 no 2_766
Cl1 H15A 3.3693 no 2_666
Cl1 H15C 3.5571 no 2_766
F1 H5 2.7530 no 2_665
F1 H10 2.8249 no 2_665
F1 H11A 2.9062 no 2_655
F1 H11C 3.5838 no 2_655
F1 H14B 3.5513 no 2_665
F1 H18 2.5390 no 1_554
F2 H11A 3.1687 no 2_655
F2 H11B 3.3490 no 2_655
F2 H11C 2.6696 no 2_655
F2 H16B 3.4489 no 2_555
F2 H16C 2.9911 no 2_555
F2 H23 2.5260 no .
F2 H24 3.0638 no .
N1 H10 3.5073 no 2_665
N1 H24 2.6428 no .
N2 H5 3.3251 no 2_665
N2 H12A 3.1602 no 1_455
N2 H14B 3.5784 no 2_665
C1 H10 3.4993 no 2_665
C1 H24 2.8376 no .
C2 H24 3.1555 no .
C3 H24 3.1835 no .
C4 H24 2.8600 no .
C5 H12B 3.5360 no 1_455
C5 H24 3.5505 no .
C6 H12A 3.0594 no 1_455
C6 H12B 3.2360 no 1_455
C7 H12A 3.1576 no 1_455
C7 H12B 3.0963 no 1_455
C8 H11C 3.5390 no 1_455
C8 H12A 3.2843 no 1_455
C8 H14A 3.2152 no 2_665
C8 H14B 3.4853 no 2_665
C9 H11B 3.4947 no 1_455
C9 H11C 3.4925 no 1_455
C9 H12A 3.2851 no 1_455
C9 H14A 3.3833 no 2_665
C9 H14B 3.1017 no 2_665
C10 H11C 3.3783 no 2_665
C10 H12B 3.2440 no 1_455
C10 H14A 3.1134 no 1_455
C11 H16A 3.5637 no 2_655
C11 H16C 3.3214 no 1_655
C11 H19 3.2577 no 2_656
C11 H24 3.5916 no .
C13 H15B 3.4339 no 2_766
C13 H15C 3.2250 no 2_766
C13 H19 3.2109 no 2_656
C13 H20 3.2731 no 2_656
C13 H25 3.4510 no .
C14 H16A 3.5329 no 2_665
C15 H13A 3.5259 no 2_766
C15 H13B 3.1448 no 2_766
C15 H25 3.5602 no .
C16 H11B 3.5288 no 1_455
C16 H11B 3.4530 no 2_655
C16 H11C 3.1980 no 1_455
C16 H14A 3.4621 no 2_665
C16 H14B 3.1956 no 2_665
C16 H16C 3.4864 no 2_555
C16 H22 3.4041 no 2_555
C16 H23 3.0184 no 2_555
C17 H14B 3.5025 no 2_666
C17 H15A 3.1729 no 2_666
C17 H15B 3.2071 no 2_666
C18 H5 3.4970 no 2_666
C18 H14B 3.2226 no 2_666
C18 H15B 3.5339 no 2_666
C18 H16A 3.5543 no 1_556
C19 H11A 3.5284 no 2_656
C19 H13C 2.9189 no 2_656
C19 H16A 3.4287 no 1_556
C19 H22 3.2599 no 2_556
C20 H13C 3.0860 no 2_656
C20 H15B 3.5050 no 2_666
C20 H20 3.3851 no 2_556
C20 H22 3.1974 no 2_556
C21 H15B 3.1936 no 2_666
C21 H20 3.3772 no 2_556
C22 H16B 3.3100 no 2_555
C22 H20 3.2357 no 2_556
C23 H13B 3.2393 no 1_455
C23 H13C 3.5028 no 1_455
C23 H16B 3.1691 no 2_555
C24 H11A 3.5904 no .
C24 H13B 3.1561 no 1_455
C25 H13A 3.5181 no .
C25 H13B 3.5192 no 1_455
C25 H15A 3.4561 no 2_666
C25 H15B 3.5848 no 2_666
C26 H15A 3.2727 no 2_666
C26 H15B 3.0265 no 2_666
B1 H5 3.4768 no 2_665
B1 H24 3.3175 no .
H5 Cl1 3.2046 no 2_666
H5 F1 2.7530 no 2_665
H5 N2 3.3251 no 2_665
H5 C18 3.4970 no 2_666
H5 B1 3.4768 no 2_665
H5 H12B 3.5482 no 1_455
H5 H18 3.0075 no 2_666
H10 Cl1 3.4045 no 2_666
H10 F1 2.8249 no 2_665
H10 N1 3.5073 no 2_665
H10 C1 3.4993 no 2_665
H10 H11C 3.0405 no 2_665
H10 H12B 3.3416 no 1_455
H10 H14A 3.0034 no 1_455
H10 H18 3.1322 no 2_666
H11A F1 2.9062 no 2_655
H11A F2 3.1687 no 2_655
H11A C19 3.5284 no 2_656
H11A C24 3.5904 no .
H11A H11C 3.3116 no 2_655
H11A H16A 3.3560 no 2_655
H11A H18 3.1587 no 2_656
H11A H19 2.8044 no 2_656
H11A H24 3.2385 no .
H11B F2 3.3490 no 2_655
H11B C9 3.4947 no 1_655
H11B C16 3.5288 no 1_655
H11B C16 3.4530 no 2_655
H11B H16A 3.0054 no 2_655
H11B H16C 2.9245 no 1_655
H11B H16C 3.0041 no 2_655
H11B H19 2.9123 no 2_656
H11B H23 3.5060 no 1_655
H11C F1 3.5838 no 2_655
H11C F2 2.6696 no 2_655
H11C C8 3.5390 no 1_655
H11C C9 3.4925 no 1_655
H11C C10 3.3783 no 2_665
H11C C16 3.1980 no 1_655
H11C H10 3.0405 no 2_665
H11C H11A 3.3116 no 2_655
H11C H16B 2.9431 no 1_655
H11C H16C 2.8182 no 1_655
H11C H16C 3.5806 no 2_655
H12A N2 3.1602 no 1_655
H12A C6 3.0594 no 1_655
H12A C7 3.1576 no 1_655
H12A C8 3.2843 no 1_655
H12A C9 3.2851 no 1_655
H12A H23 3.2786 no 1_655
H12A H24 3.5714 no 1_655
H12B Cl1 2.7401 no 2_766
H12B C5 3.5360 no 1_655
H12B C6 3.2360 no 1_655
H12B C7 3.0963 no 1_655
H12B C10 3.2440 no 1_655
H12B H5 3.5482 no 1_655
H12B H10 3.3416 no 1_655
H13A C15 3.5259 no 2_766
H13A C25 3.5181 no .
H13A H13A 3.4246 no 2_766
H13A H15B 3.3915 no 2_766
H13A H15C 2.8138 no 2_766
H13A H20 3.4330 no 2_656
H13A H25 2.7770 no .
H13B C15 3.1448 no 2_766
H13B C23 3.2393 no 1_655
H13B C24 3.1561 no 1_655
H13B C25 3.5192 no 1_655
H13B H15A 3.2971 no 2_766
H13B H15B 2.8490 no 2_766
H13B H15C 2.7861 no 2_766
H13B H20 3.3348 no 2_656
H13B H23 3.5371 no 1_655
H13B H24 3.3877 no 1_655
H13C C19 2.9189 no 2_656
H13C C20 3.0860 no 2_656
H13C C23 3.5028 no 1_655
H13C H15B 3.5395 no 2_766
H13C H19 2.2323 no 2_656
H13C H20 2.5836 no 2_656
H13C H23 3.5355 no 1_655
H13C H25 3.2687 no .
H14A Cl1 2.9501 no 2_766
H14A C8 3.2152 no 2_665
H14A C9 3.3833 no 2_665
H14A C10 3.1134 no 1_655
H14A C16 3.4621 no 2_665
H14A H10 3.0034 no 1_655
H14A H16A 3.3997 no 2_665
H14A H16B 3.0826 no 2_665
H14A H22 3.3434 no 1_665
H14B F1 3.5513 no 2_665
H14B N2 3.5784 no 2_665
H14B C8 3.4853 no 2_665
H14B C9 3.1017 no 2_665
H14B C16 3.1956 no 2_665
H14B C17 3.5025 no 2_666
H14B C18 3.2226 no 2_666
H14B H16A 2.7638 no 2_665
H14B H16B 3.2500 no 2_665
H14B H18 3.2223 no 2_666
H14B H22 3.5814 no 1_665
H15A Cl1 3.3693 no 2_666
H15A C17 3.1729 no 2_666
H15A C25 3.4561 no 2_666
H15A C26 3.2727 no 2_666
H15A H13B 3.2971 no 2_766
H15A H24 3.5761 no .
H15A H25 3.0582 no .
H15A H25 3.4283 no 2_666
H15B C13 3.4339 no 2_766
H15B C17 3.2071 no 2_666
H15B C18 3.5339 no 2_666
H15B C20 3.5050 no 2_666
H15B C21 3.1936 no 2_666
H15B C25 3.5848 no 2_666
H15B C26 3.0265 no 2_666
H15B H13A 3.3915 no 2_766
H15B H13B 2.8490 no 2_766
H15B H13C 3.5395 no 2_766
H15B H20 2.8556 no 1_665
H15B H22 3.2971 no 1_665
H15C Cl1 3.5571 no 2_766
H15C C13 3.2250 no 2_766
H15C H13A 2.8138 no 2_766
H15C H13B 2.7861 no 2_766
H15C H25 3.1752 no .
H16A C11 3.5637 no 2_655
H16A C14 3.5329 no 2_665
H16A C18 3.5543 no 1_554
H16A C19 3.4287 no 1_554
H16A H11A 3.3560 no 2_655
H16A H11B 3.0054 no 2_655
H16A H14A 3.3997 no 2_665
H16A H14B 2.7638 no 2_665
H16A H18 3.2620 no 1_554
H16A H19 2.9881 no 1_554
H16A H22 3.0962 no 2_555
H16A H23 3.0984 no 2_555
H16B F2 3.4489 no 2_555
H16B C22 3.3100 no 2_555
H16B C23 3.1691 no 2_555
H16B H11C 2.9431 no 1_455
H16B H14A 3.0826 no 2_665
H16B H14B 3.2500 no 2_665
H16B H22 2.8225 no 2_555
H16B H23 2.5187 no 2_555
H16C F2 2.9911 no 2_555
H16C C11 3.3214 no 1_455
H16C C16 3.4864 no 2_555
H16C H11B 2.9245 no 1_455
H16C H11B 3.0041 no 2_655
H16C H11C 2.8182 no 1_455
H16C H11C 3.5806 no 2_655
H16C H16C 2.5135 no 2_555
H16C H23 2.9538 no 2_555
H18 F1 2.5390 no 1_556
H18 H5 3.0075 no 2_666
H18 H10 3.1322 no 2_666
H18 H11A 3.1587 no 2_656
H18 H14B 3.2223 no 2_666
H18 H16A 3.2620 no 1_556
H19 C11 3.2577 no 2_656
H19 C13 3.2109 no 2_656
H19 H11A 2.8044 no 2_656
H19 H11B 2.9123 no 2_656
H19 H13C 2.2323 no 2_656
H19 H16A 2.9881 no 1_556
H19 H22 3.1306 no 2_556
H20 C13 3.2731 no 2_656
H20 C20 3.3851 no 2_556
H20 C21 3.3772 no 2_556
H20 C22 3.2357 no 2_556
H20 H13A 3.4330 no 2_656
H20 H13B 3.3348 no 2_656
H20 H13C 2.5836 no 2_656
H20 H15B 2.8556 no 1_445
H20 H20 3.2502 no 2_556
H20 H22 3.0508 no 2_556
H22 C16 3.4041 no 2_555
H22 C19 3.2599 no 2_556
H22 C20 3.1974 no 2_556
H22 H14A 3.3434 no 1_445
H22 H14B 3.5814 no 1_445
H22 H15B 3.2971 no 1_445
H22 H16A 3.0962 no 2_555
H22 H16B 2.8225 no 2_555
H22 H19 3.1306 no 2_556
H22 H20 3.0508 no 2_556
H23 F2 2.5260 no .
H23 C16 3.0184 no 2_555
H23 H11B 3.5060 no 1_455
H23 H12A 3.2786 no 1_455
H23 H13B 3.5371 no 1_455
H23 H13C 3.5355 no 1_455
H23 H16A 3.0984 no 2_555
H23 H16B 2.5187 no 2_555
H23 H16C 2.9538 no 2_555
H24 F2 3.0638 no .
H24 N1 2.6428 no .
H24 C1 2.8376 no .
H24 C2 3.1555 no .
H24 C3 3.1835 no .
H24 C4 2.8600 no .
H24 C5 3.5505 no .
H24 C11 3.5916 no .
H24 B1 3.3175 no .
H24 H11A 3.2385 no .
H24 H12A 3.5714 no 1_455
H24 H13B 3.3877 no 1_455
H24 H15A 3.5761 no .
H25 C13 3.4510 no .
H25 C15 3.5602 no .
H25 H13A 2.7770 no .
H25 H13C 3.2687 no .
H25 H15A 3.0582 no .
H25 H15A 3.4283 no 2_666
H25 H15C 3.1752 no .
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C4 C3 -0.1(8) no . . .
C1 N1 C4 C5 -179.6(6) no . . .
C4 N1 C1 C2 0.7(8) no . . .
C4 N1 C1 C11 179.6(6) no . . .
C1 N1 B1 F1 -62.7(10) no . . .
C1 N1 B1 F2 60.2(10) no . . .
C1 N1 B1 N2 178.8(7) no . . .
B1 N1 C1 C2 178.4(7) no . . .
B1 N1 C1 C11 -2.6(12) no . . .
C4 N1 B1 F1 114.7(8) no . . .
C4 N1 B1 F2 -122.4(8) no . . .
C4 N1 B1 N2 -3.8(10) no . . .
B1 N1 C4 C3 -177.9(6) no . . .
B1 N1 C4 C5 2.6(11) no . . .
C6 N2 C9 C8 -0.1(9) no . . .
C6 N2 C9 C16 -179.3(6) no . . .
C9 N2 C6 C5 179.3(7) no . . .
C9 N2 C6 C7 -0.8(8) no . . .
C6 N2 B1 F1 -117.9(7) no . . .
C6 N2 B1 F2 123.9(7) no . . .
C6 N2 B1 N1 2.9(10) no . . .
B1 N2 C6 C5 -0.7(11) no . . .
B1 N2 C6 C7 179.2(6) no . . .
C9 N2 B1 F1 62.0(9) no . . .
C9 N2 B1 F2 -56.2(9) no . . .
C9 N2 B1 N1 -177.2(7) no . . .
B1 N2 C9 C8 180.0(6) no . . .
B1 N2 C9 C16 0.8(12) no . . .
N1 C1 C2 C3 -1.0(9) no . . .
N1 C1 C2 C12 -177.9(6) no . . .
C11 C1 C2 C3 -179.9(7) no . . .
C11 C1 C2 C12 3.2(13) no . . .
C1 C2 C3 C4 0.9(9) no . . .
C1 C2 C3 C14 179.0(7) no . . .
C1 C2 C12 C13 -90.8(9) no . . .
C3 C2 C12 C13 92.8(10) no . . .
C12 C2 C3 C4 177.8(7) no . . .
C12 C2 C3 C14 -4.2(13) no . . .
C2 C3 C4 N1 -0.6(9) no . . .
C2 C3 C4 C5 178.9(7) no . . .
C2 C3 C14 C15 -77.4(11) no . . .
C4 C3 C14 C15 100.3(9) no . . .
C14 C3 C4 N1 -178.7(7) no . . .
C14 C3 C4 C5 0.7(13) no . . .
N1 C4 C5 C6 0.2(11) no . . .
C3 C4 C5 C6 -179.2(7) no . . .
C4 C5 C6 N2 -1.0(12) no . . .
C4 C5 C6 C7 179.1(7) no . . .
N2 C6 C7 C8 1.3(8) no . . .
N2 C6 C7 C10 179.9(7) no . . .
C5 C6 C7 C8 -178.8(8) no . . .
C5 C6 C7 C10 -0.2(15) no . . .
C6 C7 C8 C9 -1.3(8) no . . .
C6 C7 C8 C10 178.8(6) no . . 2_565
C6 C7 C10 C8 -178.4(7) no . . 2_565
C8 C7 C10 C8 -0.1(11) no . . 2_565
C10 C7 C8 C9 179.9(7) no . . .
C10 C7 C8 C10 0.1(12) no . . 2_565
C7 C8 C9 N2 0.9(9) no . . .
C7 C8 C9 C16 -179.9(7) no . . .
C7 C8 C10 C7 -0.1(11) no . 2_565 2_565
C9 C8 C10 C7 -179.9(7) no . 2_565 2_565
C10 C8 C9 N2 -179.3(8) no 2_565 . .
C10 C8 C9 C16 -0.1(14) no 2_565 . .
Cl1 C17 C18 C19 -178.2(8) no . . .
Cl1 C17 C26 C21 177.8(7) no . . .
Cl1 C17 C26 C25 -3.2(15) no . . .
C18 C17 C26 C21 -2.5(17) no . . .
C18 C17 C26 C25 176.5(11) no . . .
C26 C17 C18 C19 2.1(19) no . . .
C17 C18 C19 C20 0(2) no . . .
C18 C19 C20 C21 -2(2) no . . .
C19 C20 C21 C22 -176.6(11) no . . .
C19 C20 C21 C26 1.4(17) no . . .
C20 C21 C22 C23 180.0(10) no . . .
C20 C21 C26 C17 0.6(15) no . . .
C20 C21 C26 C25 -178.4(9) no . . .
C22 C21 C26 C17 178.7(9) no . . .
C22 C21 C26 C25 -0.3(15) no . . .
C26 C21 C22 C23 2.0(16) no . . .
C21 C22 C23 C24 -2.6(18) no . . .
C22 C23 C24 C25 1.7(19) no . . .
C23 C24 C25 C26 -0.0(18) no . . .
C24 C25 C26 C17 -179.6(11) no . . .
C24 C25 C26 C21 -0.6(17) no . . .
