#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:21:23 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/78/7127828.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_7127828
loop_
_publ_author_name
'Mu, Huiying'
'Miki, Koji'
'Kubo, Takuya'
'Otsuka, Koji'
'Ohe, Kouichi'
_publ_section_title
;
 Substituted meso-vinyl-BODIPY as thiol-selective fluorogenic
 probes for sensing unfolded proteins in the endoplasmic reticulum.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1818
_journal_page_last               1821
_journal_paper_doi               10.1039/d0cc08160d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C15 H16 B Cl F2 N2'
_chemical_formula_sum            'C15 H16 B Cl F2 N2'
_chemical_formula_weight         308.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-09-30 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                109.950(10)
_cell_angle_beta                 102.666(11)
_cell_angle_gamma                98.075(6)
_cell_formula_units_Z            2
_cell_length_a                   8.337(8)
_cell_length_b                   8.954(9)
_cell_length_c                   10.867(11)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    143
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     723.2(12)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      143
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5879
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3162
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0001Fo² + 1.4900σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                2294
_reflns_number_total             3162
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0cc08160d2.cif
_cod_data_source_block           20200909-04
_cod_depositor_comments          'Adding full bibliography for 7127828.cif.'
_cod_database_code               7127828
loop_
_space_group_symop_id
_space_group_symop_operation_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_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.04412(6) -0.06841(7) -0.29361(5) 0.03070(15) Uani 0.8 2 d . . .
Cl2 Cl 0.8995(3) 0.3324(3) 0.5724(3) 0.0454(8) Uani 0.2 2 d . . .
F1 F 0.50221(11) 0.42808(11) 0.13356(9) 0.0299(3) Uani 1 2 d . . .
F2 F 0.29709(12) 0.40233(12) 0.23685(10) 0.0308(3) Uani 1 2 d . . .
N1 N 0.30595(16) 0.16694(16) 0.04851(14) 0.0235(4) Uani 1 2 d . . .
N2 N 0.52292(17) 0.26824(17) 0.27249(13) 0.0246(4) Uani 1 2 d . . .
C1 C 0.1927(2) 0.1614(2) -0.06398(17) 0.0251(5) Uani 1 2 d . . .
C2 C 0.1112(2) -0.0024(2) -0.14271(17) 0.0263(5) Uani 1 2 d . . .
C3 C 0.1739(2) -0.1016(2) -0.08062(17) 0.0250(5) Uani 1 2 d . . .
C4 C 0.2968(2) 0.0068(2) 0.04180(17) 0.0224(4) Uani 1 2 d . . .
C5 C 0.3990(2) -0.0225(2) 0.14764(17) 0.0238(5) Uani 1 2 d . . .
C6 C 0.5142(2) 0.1063(2) 0.26037(17) 0.0243(5) Uani 1 2 d . . .
C7 C 0.6417(2) 0.1086(2) 0.37263(18) 0.0292(5) Uani 1 2 d . . .
C8 C 0.7193(3) 0.2707(3) 0.4476(2) 0.0356(6) Uani 1 2 d . . .
C9 C 0.6448(2) 0.3671(2) 0.38608(18) 0.0291(5) Uani 1 2 d . . .
C10 C 0.1686(3) 0.3095(3) -0.0911(2) 0.0326(6) Uani 1 2 d . . .
C11 C 0.1197(3) -0.2843(2) -0.1361(2) 0.0315(5) Uani 1 2 d . . .
C12 C 0.6913(3) -0.0309(3) 0.4055(2) 0.0372(6) Uani 1 2 d . . .
C13 C 0.6866(3) 0.5483(3) 0.4333(2) 0.0405(6) Uani 1 2 d . . .
C14 C 0.3800(2) -0.1908(2) 0.14295(19) 0.0284(5) Uani 1 2 d . . .
C15 C 0.3175(3) -0.2368(3) 0.2288(2) 0.0396(6) Uani 1 2 d . . .
B1 B 0.4068(2) 0.3225(2) 0.1740(2) 0.0254(5) Uani 1 2 d . . .
H1 H 0.269(3) 0.368(3) -0.106(2) 0.071(7) Uiso 1 2 d . . .
H2 H 0.152(3) 0.399(3) -0.012(2) 0.063(7) Uiso 1 2 d . . .
H3 H 0.076(3) 0.285(3) -0.163(2) 0.055(7) Uiso 1 2 d . . .
H4 H 0.030(3) -0.320(3) -0.224(2) 0.068(7) Uiso 1 2 d . . .
H5 H 0.217(3) -0.336(2) -0.151(2) 0.052(6) Uiso 1 2 d . . .
H6 H 0.077(2) -0.324(2) -0.070(2) 0.062(7) Uiso 1 2 d . . .
H7 H 0.687(2) -0.121(2) 0.324(2) 0.046(6) Uiso 1 2 d . . .
H8 H 0.603(2) -0.086(2) 0.447(2) 0.057(6) Uiso 1 2 d . . .
H9 H 0.806(2) 0.005(2) 0.464(2) 0.048(6) Uiso 1 2 d . . .
H10 H 0.752(3) 0.602(3) 0.528(2) 0.060(7) Uiso 1 2 d . . .
H11 H 0.581(3) 0.591(3) 0.420(2) 0.079(8) Uiso 1 2 d . . .
H12 H 0.755(3) 0.585(3) 0.390(2) 0.074(8) Uiso 1 2 d . . .
H13 H 0.780(3) 0.307(3) 0.505(3) 0.073(10) Uiso 1 2 d . . .
H14 H 0.411(2) -0.263(2) 0.0727(19) 0.045(6) Uiso 1 2 d . . .
H15 H 0.304(2) -0.349(3) 0.2277(19) 0.053(6) Uiso 1 2 d . . .
H16 H 0.277(2) -0.153(3) 0.300(2) 0.062(7) Uiso 1 2 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(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 108.26(12) yes . .
C1 N1 B1 126.08(17) yes . .
C4 N1 B1 124.97(16) yes . .
C6 N2 C9 108.82(16) yes . .
C6 N2 B1 125.19(12) yes . .
C9 N2 B1 125.95(17) yes . .
N1 C1 C2 107.74(18) yes . .
N1 C1 C10 123.00(14) yes . .
C2 C1 C10 129.25(17) yes . .
Cl1 C2 C1 124.39(16) yes . .
Cl1 C2 C3 125.27(13) yes . .
C1 C2 C3 110.34(16) yes . .
C2 C3 C4 104.92(17) yes . .
C2 C3 C11 125.65(15) yes . .
C4 C3 C11 129.43(19) yes . .
N1 C4 C3 108.74(17) yes . .
N1 C4 C5 120.21(12) yes . .
C3 C4 C5 131.05(18) yes . .
C4 C5 C6 120.92(18) yes . .
C4 C5 C14 119.41(13) yes . .
C6 C5 C14 119.62(18) yes . .
N2 C6 C5 120.37(17) yes . .
N2 C6 C7 107.63(13) yes . .
C5 C6 C7 131.91(19) yes . .
C6 C7 C8 105.4(2) yes . .
C6 C7 C12 129.59(15) yes . .
C8 C7 C12 124.98(19) yes . .
Cl2 C8 C7 122.8(2) yes . .
Cl2 C8 C9 126.1(2) yes . .
C7 C8 C9 109.91(18) yes . .
N2 C9 C8 108.22(18) yes . .
N2 C9 C13 123.61(19) yes . .
C8 C9 C13 128.17(17) yes . .
C5 C14 C15 122.28(18) yes . .
F1 B1 F2 108.94(17) yes . .
F1 B1 N1 109.89(17) yes . .
F1 B1 N2 110.40(15) yes . .
F2 B1 N1 110.24(15) yes . .
F2 B1 N2 110.25(18) yes . .
N1 B1 N2 107.11(17) yes . .
C8 Cl2 H13 9.0(15) no . .
Cl2 C8 H13 14(3) no . .
C7 C8 H13 132(3) no . .
C9 C8 H13 118(3) no . .
C1 C10 H1 114.4(15) no . .
C1 C10 H2 113.9(16) no . .
C1 C10 H3 111.1(15) no . .
H1 C10 H2 101.0(18) no . .
H1 C10 H3 110(2) no . .
H2 C10 H3 106.0(19) no . .
C3 C11 H4 107.7(14) no . .
C3 C11 H5 111.6(11) no . .
C3 C11 H6 111.8(11) no . .
H4 C11 H5 110.2(17) no . .
H4 C11 H6 110.4(18) no . .
H5 C11 H6 105.2(19) no . .
C7 C12 H7 111.5(15) no . .
C7 C12 H8 113.2(12) no . .
C7 C12 H9 109.0(14) no . .
H7 C12 H8 102.1(17) no . .
H7 C12 H9 107.8(17) no . .
H8 C12 H9 112.9(18) no . .
C9 C13 H10 113.0(16) no . .
C9 C13 H11 111.5(13) no . .
C9 C13 H12 112.5(14) no . .
H10 C13 H11 108.5(19) no . .
H10 C13 H12 103(2) no . .
H11 C13 H12 108(2) no . .
C5 C14 H14 115.1(15) no . .
C15 C14 H14 122.6(15) no . .
C14 C15 H15 123.6(13) no . .
C14 C15 H16 118.6(15) no . .
H15 C15 H16 117.8(19) no . .
Cl2 H13 C8 156(4) 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 C2 1.705(2) yes .
Cl2 C8 1.663(3) yes .
F1 B1 1.395(3) yes .
F2 B1 1.393(3) yes .
N1 C1 1.352(2) yes .
N1 C4 1.401(3) yes .
N1 B1 1.542(2) yes .
N2 C6 1.400(3) yes .
N2 C9 1.338(2) yes .
N2 B1 1.533(3) yes .
C1 C2 1.398(2) yes .
C1 C10 1.484(4) yes .
C2 C3 1.379(3) yes .
C3 C4 1.416(2) yes .
C3 C11 1.497(3) yes .
C4 C5 1.399(3) yes .
C5 C6 1.401(2) yes .
C5 C14 1.475(3) yes .
C6 C7 1.424(3) yes .
C7 C8 1.374(3) yes .
C7 C12 1.498(4) yes .
C8 C9 1.393(4) yes .
C9 C13 1.488(3) yes .
C14 C15 1.313(4) yes .
Cl2 H13 1.04(2) no .
C8 H13 0.66(2) no .
C10 H1 1.00(3) no .
C10 H2 1.01(2) no .
C10 H3 0.91(2) no .
C11 H4 0.99(2) no .
C11 H5 1.01(2) no .
C11 H6 1.01(3) no .
C12 H7 0.962(19) no .
C12 H8 1.08(2) no .
C12 H9 0.967(18) no .
C13 H10 0.96(2) no .
C13 H11 1.01(3) no .
C13 H12 0.91(3) no .
C14 H14 0.93(2) no .
C15 H15 0.99(2) no .
C15 H16 1.03(2) 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_1
_geom_contact_site_symmetry_2
Cl1 C10 3.310(3) no . .
Cl1 C11 3.241(3) no . .
Cl2 C12 3.146(4) no . .
Cl2 C13 3.310(5) no . .
F1 C1 3.051(2) no . .
F1 C6 3.597(4) no . .
F1 C9 3.003(3) no . .
F1 C10 3.041(3) no . .
F1 C13 3.013(4) no . .
F2 C1 3.084(3) no . .
F2 C4 3.451(4) no . .
F2 C6 3.460(3) no . .
F2 C9 3.111(3) no . .
F2 C10 3.255(4) no . .
F2 C13 3.267(3) no . .
N1 C6 2.824(3) no . .
N2 C4 2.828(2) no . .
C1 C5 3.550(4) no . .
C2 C5 3.597(4) no . .
C3 C14 3.061(4) no . .
C4 C15 3.448(4) no . .
C5 C9 3.547(3) no . .
C5 C11 3.288(3) no . .
C5 C12 3.316(4) no . .
C5 B1 2.994(4) no . .
C6 C15 3.140(4) no . .
C7 C14 3.095(3) no . .
C7 C15 3.436(4) no . .
C10 B1 3.075(4) no . .
C11 C14 3.078(4) no . .
C12 C14 3.138(3) no . .
C12 C15 3.185(4) no . .
C13 B1 3.062(3) no . .
Cl1 C12 3.534(4) no . 2_655
Cl2 F2 3.442(4) no . 2_666
Cl2 C13 3.487(5) no . 2_766
Cl2 C15 3.349(5) no . 2_656
F1 F1 3.550(3) no . 2_665
F1 C10 3.571(4) no . 2_665
F1 C11 3.567(4) no . 2_655
F1 C14 3.469(3) no . 2_655
F1 C15 3.511(4) no . 1_565
F2 Cl2 3.442(4) no . 2_666
F2 C11 3.302(4) no . 2_555
F2 C13 3.427(5) no . 2_666
F2 C15 3.244(4) no . 1_565
C2 C7 3.547(4) no . 2_655
C3 C6 3.576(4) no . 2_655
C6 C3 3.576(4) no . 2_655
C7 C2 3.547(4) no . 2_655
C10 F1 3.571(4) no . 2_665
C11 F1 3.567(4) no . 2_655
C11 F2 3.302(4) no . 2_555
C12 Cl1 3.534(4) no . 2_655
C13 Cl2 3.487(5) no . 2_766
C13 F2 3.427(5) no . 2_666
C14 F1 3.469(3) no . 2_655
C15 Cl2 3.349(5) no . 2_656
C15 F1 3.511(4) no . 1_545
C15 F2 3.244(4) no . 1_545
Cl1 H3 2.91(2) no . .
Cl1 H4 2.72(3) no . .
Cl2 H9 2.680(19) no . .
Cl2 H10 2.99(3) no . .
F1 H1 2.72(2) no . .
F1 H2 2.93(2) no . .
F1 H11 2.83(2) no . .
F1 H12 2.84(2) no . .
F2 H1 3.59(2) no . .
F2 H2 2.70(2) no . .
F2 H11 2.63(2) no . .
N1 H1 2.86(3) no . .
N1 H2 2.78(3) no . .
N1 H3 3.22(3) no . .
N2 H10 3.271(18) no . .
N2 H11 2.70(2) no . .
N2 H12 2.89(2) no . .
N2 H13 2.81(3) no . .
C2 H1 3.25(2) no . .
C2 H2 3.32(2) no . .
C2 H3 2.71(3) no . .
C2 H4 2.61(2) no . .
C2 H5 3.21(2) no . .
C2 H6 3.23(3) no . .
C3 H14 3.12(2) no . .
C4 H4 3.382(17) no . .
C4 H5 2.949(18) no . .
C4 H6 2.945(19) no . .
C4 H14 2.81(2) no . .
C4 H16 3.58(3) no . .
C5 H5 3.338(16) no . .
C5 H6 3.306(16) no . .
C5 H7 3.16(2) no . .
C5 H8 3.59(2) no . .
C5 H15 3.37(3) no . .
C5 H16 2.62(3) no . .
C6 H7 2.84(2) no . .
C6 H8 3.11(3) no . .
C6 H9 3.36(2) no . .
C6 H13 2.87(2) no . .
C6 H14 3.105(18) no . .
C6 H16 3.04(2) no . .
C7 H16 3.32(2) no . .
C8 H7 3.25(2) no . .
C8 H8 3.20(2) no . .
C8 H9 2.63(2) no . .
C8 H10 2.75(2) no . .
C8 H11 3.32(3) no . .
C8 H12 3.08(3) no . .
C11 H14 2.868(19) no . .
C12 H13 2.77(3) no . .
C12 H14 3.558(16) no . .
C12 H16 3.286(19) no . .
C13 H13 2.69(3) no . .
C14 H5 2.916(18) no . .
C14 H6 2.807(18) no . .
C14 H7 2.708(18) no . .
C14 H8 3.153(19) no . .
C15 H6 3.19(2) no . .
C15 H7 2.934(18) no . .
C15 H8 2.747(17) no . .
B1 H1 3.20(2) no . .
B1 H2 2.92(2) no . .
B1 H11 2.825(19) no . .
B1 H12 3.285(19) no . .
H5 H14 2.41(3) no . .
H6 H14 2.75(3) no . .
H6 H15 3.47(3) no . .
H7 H13 3.54(3) no . .
H7 H14 2.91(2) no . .
H7 H15 3.27(3) no . .
H7 H16 3.34(3) no . .
H8 H13 3.40(4) no . .
H8 H15 3.06(2) no . .
H8 H16 2.70(3) no . .
H9 H13 2.64(4) no . .
H10 H13 2.61(4) no . .
H11 H13 3.49(4) no . .
H12 H13 3.16(4) no . .
H14 H15 2.36(3) no . .
H14 H16 2.86(3) no . .
Cl1 H7 3.36(2) no . 2_655
Cl1 H8 3.54(2) no . 1_454
Cl1 H9 2.98(2) no . 1_454
Cl1 H9 3.12(2) no . 2_655
Cl1 H10 2.931(19) no . 1_444
Cl1 H16 2.97(2) no . 2_555
Cl2 H3 3.12(3) no . 1_656
Cl2 H4 3.010(19) no . 1_666
Cl2 H10 3.36(3) no . 2_766
Cl2 H12 2.77(2) no . 2_766
Cl2 H15 3.01(2) no . 2_656
Cl2 H16 2.90(3) no . 2_656
F1 H1 2.59(2) no . 2_665
F1 H5 2.58(2) no . 2_655
F1 H14 3.21(2) no . 1_565
F1 H14 2.55(2) no . 2_655
F1 H15 2.83(2) no . 1_565
F2 H4 2.68(2) no . 2_555
F2 H6 3.088(19) no . 2_555
F2 H10 2.69(3) no . 2_666
F2 H13 3.36(3) no . 2_666
F2 H15 2.25(2) no . 1_565
N1 H14 3.10(2) no . 2_655
N2 H5 2.87(2) no . 2_655
N2 H10 3.54(3) no . 2_666
N2 H11 3.49(3) no . 2_666
C1 H6 3.19(2) no . 2_555
C1 H7 3.13(2) no . 2_655
C1 H14 3.33(2) no . 2_655
C2 H7 3.22(2) no . 2_655
C6 H5 3.50(2) no . 2_655
C6 H8 3.58(2) no . 2_656
C7 H8 3.16(2) no . 2_656
C7 H16 3.35(2) no . 2_656
C8 H8 3.56(2) no . 2_656
C8 H11 3.33(3) no . 2_666
C8 H15 3.41(2) no . 2_656
C8 H16 3.26(3) no . 2_656
C9 H4 3.54(3) no . 2_655
C9 H5 2.97(2) no . 2_655
C9 H11 3.09(3) no . 2_666
C10 H5 3.44(2) no . 1_565
C10 H6 3.41(2) no . 1_565
C10 H6 2.96(2) no . 2_555
C10 H7 3.11(2) no . 2_655
C10 H14 3.56(2) no . 2_655
C10 H15 3.564(17) no . 1_565
C11 H1 3.60(3) no . 1_545
C11 H2 3.55(3) no . 1_545
C11 H2 3.29(3) no . 2_555
C11 H12 3.59(2) no . 2_655
C12 H8 3.32(2) no . 2_656
C12 H11 3.44(3) no . 1_545
C12 H12 3.51(3) no . 1_545
C12 H16 2.99(2) no . 2_656
C13 H5 3.35(2) no . 2_655
C13 H7 3.54(3) no . 1_565
C13 H8 3.40(2) no . 1_565
C13 H11 3.35(3) no . 2_666
C14 H1 3.56(3) no . 2_655
C14 H2 3.52(2) no . 1_545
C15 H2 3.276(19) no . 1_545
C15 H3 3.13(2) no . 2_555
C15 H8 3.566(18) no . 2_656
C15 H11 3.56(3) no . 1_545
C15 H13 3.40(3) no . 2_656
B1 H5 3.19(2) no . 2_655
B1 H14 3.29(2) no . 2_655
B1 H15 3.08(2) no . 1_565
H1 F1 2.59(2) no . 2_665
H1 C11 3.60(3) no . 1_565
H1 C14 3.56(3) no . 2_655
H1 H5 2.92(4) no . 1_565
H1 H6 3.33(3) no . 1_565
H1 H7 2.77(3) no . 2_655
H1 H12 3.21(4) no . 2_665
H1 H14 3.10(3) no . 1_565
H1 H14 2.95(3) no . 2_655
H1 H15 3.56(3) no . 1_565
H2 C11 3.55(3) no . 1_565
H2 C11 3.29(3) no . 2_555
H2 C14 3.52(2) no . 1_565
H2 C15 3.276(19) no . 1_565
H2 H2 3.32(3) no . 2_565
H2 H4 3.46(4) no . 2_555
H2 H5 3.26(4) no . 1_565
H2 H6 2.87(4) no . 1_565
H2 H6 2.38(3) no . 2_555
H2 H14 3.18(3) no . 1_565
H2 H15 2.69(2) no . 1_565
H3 Cl2 3.12(3) no . 1_454
H3 C15 3.13(2) no . 2_555
H3 H5 3.38(3) no . 1_565
H3 H6 3.29(3) no . 1_565
H3 H6 3.01(4) no . 2_555
H3 H7 3.12(3) no . 2_655
H3 H12 3.52(4) no . 2_665
H3 H15 3.26(3) no . 2_555
H3 H16 2.85(3) no . 2_555
H4 Cl2 3.010(19) no . 1_444
H4 F2 2.68(2) no . 2_555
H4 C9 3.54(3) no . 2_655
H4 H2 3.46(4) no . 2_555
H4 H10 2.94(3) no . 1_444
H4 H12 3.43(3) no . 2_655
H4 H13 3.58(3) no . 1_444
H5 F1 2.58(2) no . 2_655
H5 N2 2.87(2) no . 2_655
H5 C6 3.50(2) no . 2_655
H5 C9 2.97(2) no . 2_655
H5 C10 3.44(2) no . 1_545
H5 C13 3.35(2) no . 2_655
H5 B1 3.19(2) no . 2_655
H5 H1 2.92(4) no . 1_545
H5 H2 3.26(4) no . 1_545
H5 H3 3.38(3) no . 1_545
H5 H12 2.86(3) no . 2_655
H6 F2 3.088(19) no . 2_555
H6 C1 3.19(2) no . 2_555
H6 C10 3.41(2) no . 1_545
H6 C10 2.96(2) no . 2_555
H6 H1 3.33(3) no . 1_545
H6 H2 2.87(4) no . 1_545
H6 H2 2.38(3) no . 2_555
H6 H3 3.29(3) no . 1_545
H6 H3 3.01(4) no . 2_555
H7 Cl1 3.36(2) no . 2_655
H7 C1 3.13(2) no . 2_655
H7 C2 3.22(2) no . 2_655
H7 C10 3.11(2) no . 2_655
H7 C13 3.54(3) no . 1_545
H7 H1 2.77(3) no . 2_655
H7 H3 3.12(3) no . 2_655
H7 H11 3.17(4) no . 1_545
H7 H12 3.04(4) no . 1_545
H8 Cl1 3.54(2) no . 1_656
H8 C6 3.58(2) no . 2_656
H8 C7 3.16(2) no . 2_656
H8 C8 3.56(2) no . 2_656
H8 C12 3.32(2) no . 2_656
H8 C13 3.40(2) no . 1_545
H8 C15 3.566(18) no . 2_656
H8 H8 2.66(3) no . 2_656
H8 H10 3.50(4) no . 1_545
H8 H11 2.78(3) no . 1_545
H8 H12 3.29(3) no . 1_545
H8 H16 2.71(2) no . 2_656
H9 Cl1 2.98(2) no . 1_656
H9 Cl1 3.12(2) no . 2_655
H9 H9 3.18(3) no . 2_756
H9 H12 3.51(3) no . 1_545
H9 H16 2.74(3) no . 2_656
H10 Cl1 2.931(19) no . 1_666
H10 Cl2 3.36(3) no . 2_766
H10 F2 2.69(3) no . 2_666
H10 N2 3.54(3) no . 2_666
H10 H4 2.94(3) no . 1_666
H10 H8 3.50(4) no . 1_565
H10 H11 3.32(4) no . 2_666
H11 N2 3.49(3) no . 2_666
H11 C8 3.33(3) no . 2_666
H11 C9 3.09(3) no . 2_666
H11 C12 3.44(3) no . 1_565
H11 C13 3.35(3) no . 2_666
H11 C15 3.56(3) no . 1_565
H11 H7 3.17(4) no . 1_565
H11 H8 2.78(3) no . 1_565
H11 H10 3.32(4) no . 2_666
H11 H11 3.14(4) no . 2_666
H11 H13 3.45(4) no . 2_666
H11 H15 2.99(3) no . 1_565
H12 Cl2 2.77(2) no . 2_766
H12 C11 3.59(2) no . 2_655
H12 C12 3.51(3) no . 1_565
H12 H1 3.21(4) no . 2_665
H12 H3 3.52(4) no . 2_665
H12 H4 3.43(3) no . 2_655
H12 H5 2.86(3) no . 2_655
H12 H7 3.04(4) no . 1_565
H12 H8 3.29(3) no . 1_565
H12 H9 3.51(3) no . 1_565
H13 F2 3.36(3) no . 2_666
H13 C15 3.40(3) no . 2_656
H13 H4 3.58(3) no . 1_666
H13 H11 3.45(4) no . 2_666
H13 H15 3.05(4) no . 2_656
H13 H16 2.98(4) no . 2_656
H14 F1 3.21(2) no . 1_545
H14 F1 2.55(2) no . 2_655
H14 N1 3.10(2) no . 2_655
H14 C1 3.33(2) no . 2_655
H14 C10 3.56(2) no . 2_655
H14 B1 3.29(2) no . 2_655
H14 H1 3.10(3) no . 1_545
H14 H1 2.95(3) no . 2_655
H14 H2 3.18(3) no . 1_545
H15 Cl2 3.01(2) no . 2_656
H15 F1 2.83(2) no . 1_545
H15 F2 2.25(2) no . 1_545
H15 C8 3.41(2) no . 2_656
H15 C10 3.564(17) no . 1_545
H15 B1 3.08(2) no . 1_545
H15 H1 3.56(3) no . 1_545
H15 H2 2.69(2) no . 1_545
H15 H3 3.26(3) no . 2_555
H15 H11 2.99(3) no . 1_545
H15 H13 3.05(4) no . 2_656
H16 Cl1 2.97(2) no . 2_555
H16 Cl2 2.90(3) no . 2_656
H16 C7 3.35(2) no . 2_656
H16 C8 3.26(3) no . 2_656
H16 C12 2.99(2) no . 2_656
H16 H3 2.85(3) no . 2_555
H16 H8 2.71(2) no . 2_656
H16 H9 2.74(3) no . 2_656
H16 H13 2.98(4) no . 2_656
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C4 C3 0.54(19) no . . . .
C1 N1 C4 C5 -178.69(15) no . . . .
C4 N1 C1 C2 -0.01(19) no . . . .
C4 N1 C1 C10 -179.68(15) no . . . .
C1 N1 B1 F1 -58.1(2) no . . . .
C1 N1 B1 F2 62.0(3) no . . . .
C1 N1 B1 N2 -178.05(16) no . . . .
B1 N1 C1 C2 -170.79(15) no . . . .
B1 N1 C1 C10 9.5(3) no . . . .
C4 N1 B1 F1 132.60(18) no . . . .
C4 N1 B1 F2 -107.3(2) no . . . .
C4 N1 B1 N2 12.7(2) no . . . .
B1 N1 C4 C3 171.44(15) no . . . .
B1 N1 C4 C5 -7.8(3) no . . . .
C6 N2 C9 C8 1.3(2) no . . . .
C6 N2 C9 C13 -178.38(16) no . . . .
C9 N2 C6 C5 -178.35(15) no . . . .
C9 N2 C6 C7 -1.3(2) no . . . .
C6 N2 B1 F1 -130.24(17) no . . . .
C6 N2 B1 F2 109.34(18) no . . . .
C6 N2 B1 N1 -10.6(2) no . . . .
B1 N2 C6 C5 3.7(3) no . . . .
B1 N2 C6 C7 -179.22(15) no . . . .
C9 N2 B1 F1 52.2(2) no . . . .
C9 N2 B1 F2 -68.2(2) no . . . .
C9 N2 B1 N1 171.82(16) no . . . .
B1 N2 C9 C8 179.20(15) no . . . .
B1 N2 C9 C13 -0.5(3) no . . . .
N1 C1 C2 Cl1 179.25(14) no . . . .
N1 C1 C2 C3 -0.5(2) no . . . .
C10 C1 C2 Cl1 -1.1(3) no . . . .
C10 C1 C2 C3 179.10(19) no . . . .
Cl1 C2 C3 C4 -178.94(12) no . . . .
Cl1 C2 C3 C11 1.5(3) no . . . .
C1 C2 C3 C4 0.8(2) no . . . .
C1 C2 C3 C11 -178.72(15) no . . . .
C2 C3 C4 N1 -0.8(2) no . . . .
C2 C3 C4 C5 178.28(17) no . . . .
C11 C3 C4 N1 178.70(18) no . . . .
C11 C3 C4 C5 -2.2(3) no . . . .
N1 C4 C5 C6 -1.3(3) no . . . .
N1 C4 C5 C14 176.17(14) no . . . .
C3 C4 C5 C6 179.68(17) no . . . .
C3 C4 C5 C14 -2.9(3) no . . . .
C4 C5 C6 N2 3.3(3) no . . . .
C4 C5 C6 C7 -172.96(17) no . . . .
C4 C5 C14 C15 -111.1(2) no . . . .
C6 C5 C14 C15 66.4(2) no . . . .
C14 C5 C6 N2 -174.19(16) no . . . .
C14 C5 C6 C7 9.6(3) no . . . .
N2 C6 C7 C8 0.8(2) no . . . .
N2 C6 C7 C12 -177.25(17) no . . . .
C5 C6 C7 C8 177.34(19) no . . . .
C5 C6 C7 C12 -0.7(4) no . . . .
C6 C7 C8 Cl2 -168.25(18) no . . . .
C6 C7 C8 C9 0.0(2) no . . . .
C12 C7 C8 Cl2 9.9(4) no . . . .
C12 C7 C8 C9 178.15(19) no . . . .
Cl2 C8 C9 N2 166.9(2) no . . . .
Cl2 C8 C9 C13 -13.4(4) no . . . .
C7 C8 C9 N2 -0.8(3) no . . . .
C7 C8 C9 C13 178.83(18) no . . . .
