#------------------------------------------------------------------------------
#$Date: 2022-02-23 00:55:21 +0200 (Wed, 23 Feb 2022) $
#$Revision: 273113 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129746.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_7129746
loop_
_publ_author_name
'Wang, Ling-Yun'
'Liu, Zheng Fei'
'Teng, Kun-Xu'
'Niu, Li-Ya'
'Yang, Qing-Zheng'
_publ_section_title
;
 Circularly Polarized Luminescence from Helical N,O-Boron-Chelated
 Dipyrromethenes (BODIPY) Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06051A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H24 B Cl2 F N2 O2'
_chemical_formula_sum            'C39 H24 B Cl2 F N2 O2'
_chemical_formula_weight         653.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2799f9
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-23 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.391(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1863(4)
_cell_length_b                   10.3824(2)
_cell_length_c                   13.6545(5)
_cell_measurement_reflns_used    5900
_cell_measurement_temperature    301.13(11)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      3.6570
_cell_volume                     1644.53(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.13(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -26.00   0.50    0.10    --  -47.95  48.00 113.00   50
  2  ω    -17.00  25.00   0.50    0.10    --  -47.95  48.00 113.00   84
  3  ω   -118.00 -66.00   0.50    0.10    --  -47.95 -48.00 -34.00  104
  4  ω    -63.00 -35.00   0.50    0.10    --  -47.95 -48.00 -34.00   56
  5  ω     -8.00  17.00   0.50    0.10    --   47.95 -48.00 -34.00   50
  6  ω     91.00 177.00   0.50    0.50    --  104.75  48.00 113.00  172
  7  ω    -24.00  28.00   0.50    0.10    --  -47.95  19.00 -90.00  104
  8  ω   -119.00 -74.00   0.50    0.10    --  -47.95-125.00 -90.00   90
  9  ω   -119.00 -72.00   0.50    0.10    --  -47.95-125.00  90.00   94
 10  ω     72.00 101.00   0.50    0.10    --   47.95  48.00 113.00   58
 11  ω   -102.00 -29.00   0.50    0.50    -- -102.00  77.00-180.00  146
 12  ω    -60.00 -32.00   0.50    0.50    -- -102.00  61.00-120.00   56
 13  ω   -175.00 -86.00   0.50    0.50    -- -102.00 -61.00  60.00  178
 14  ω   -154.00-118.00   0.50    0.50    -- -102.00 -61.00  90.00   72
 15  ω    -68.00 -42.00   0.50    0.50    -- -102.00  61.00  60.00   52
 16  ω   -113.00 -86.00   0.50    0.50    -- -102.00 -61.00  90.00   54
 17  ω    -99.00 -74.00   0.50    0.50    -- -102.00  77.00  30.00   50
 18  ω    -54.00 -29.00   0.50    0.50    -- -102.00  77.00  30.00   50
 19  ω   -172.00-111.00   0.50    0.50    -- -102.00 -48.00 -34.00  122
 20  ω     70.00 109.00   0.50    0.50    --  104.75 -94.00 150.00   78
 21  ω     33.00  58.00   0.50    0.50    --  104.75 -94.00 150.00   50
 22  ω     32.00  72.00   0.50    0.50    --  104.75 -61.00 -30.00   80
 23  ω    140.00 177.00   0.50    0.50    --  104.75  30.00-150.00   74
 24  ω    104.00 137.00   0.50    0.50    --  104.75  30.00-150.00   66
 25  ω     32.00  70.00   0.50    0.50    --  104.75 -61.00-180.00   76
 26  ω     38.00  73.00   0.50    0.50    --  104.75 -61.00 -90.00   70
 27  ω     40.00  68.00   0.50    0.50    --  104.75 -61.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1185525000
_diffrn_orient_matrix_UB_12      0.0667912000
_diffrn_orient_matrix_UB_13      -0.0505932000
_diffrn_orient_matrix_UB_21      0.0211400000
_diffrn_orient_matrix_UB_22      0.0570855000
_diffrn_orient_matrix_UB_23      -0.0928604000
_diffrn_orient_matrix_UB_31      -0.0559526000
_diffrn_orient_matrix_UB_32      -0.1196093000
_diffrn_orient_matrix_UB_33      -0.0725162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12505
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.897
_diffrn_reflns_theta_min         3.680
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark purple'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(13)
_refine_ls_extinction_coef       0.0014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0396
_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)+(0.0548P)²+0.0287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.524
_reflns_number_gt                4498
_reflns_number_total             5178
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06051a2.cif
_cod_data_source_block           20200910a
_cod_original_cell_volume        1644.54(11)
_cod_database_code               7129746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1B1F1Cl1
_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_max   0.939
_shelx_estimated_absorpt_t_min   0.568
_diffrn_oxdiff_digest_frames
;
01906ab4e2db5f3a4dd2677f18248a3c6902192a947
;
_diffrn_oxdiff_digest_hkl
;
01f5f7f023d13b77755e295b4c11405112017d
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C28(H28), C29(H29), C31(H31),
  C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.273
_oxdiff_exptl_absorpt_empirical_full_min 0.567
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
Cl1 Cl 0.08011(14) -0.19495(14) -0.99424(10) 0.1083(5) Uani 1 1 d . . . . .
Cl2 Cl -0.28946(8) -0.02770(12) -0.81076(10) 0.0882(3) Uani 1 1 d . . . . .
F1 F 0.21403(17) 0.5334(2) -0.65920(16) 0.0609(5) Uani 1 1 d . . . . .
O1 O 0.12320(17) 0.39986(19) -0.58899(18) 0.0487(5) Uani 1 1 d . . . . .
O2 O 0.3669(2) 0.0422(2) -0.4860(2) 0.0766(8) Uani 1 1 d . . . . .
N1 N 0.1963(2) 0.6193(2) -0.5050(2) 0.0442(5) Uani 1 1 d . . . . .
N2 N 0.3247(2) 0.4396(2) -0.4773(2) 0.0475(6) Uani 1 1 d . . . . .
C1 C -0.2412(4) 0.5191(5) -0.8529(4) 0.0897(14) Uani 1 1 d . . . . .
H1 H -0.1807 0.4974 -0.8667 0.108 Uiso 1 1 calc R . . . .
C2 C -0.3530(6) 0.4772(6) -0.9251(4) 0.118(2) Uani 1 1 d . . . . .
H2 H -0.3673 0.4272 -0.9868 0.142 Uiso 1 1 calc R . . . .
C3 C -0.4423(6) 0.5107(8) -0.9041(6) 0.130(3) Uani 1 1 d . . . . .
H3 H -0.5168 0.4821 -0.9508 0.156 Uiso 1 1 calc R . . . .
C4 C -0.4211(4) 0.5837(9) -0.8171(6) 0.131(3) Uani 1 1 d . . . . .
H4 H -0.4822 0.6078 -0.8050 0.157 Uiso 1 1 calc R . . . .
C5 C -0.3122(3) 0.6251(6) -0.7440(4) 0.0877(13) Uani 1 1 d . . . . .
H5 H -0.3000 0.6751 -0.6829 0.105 Uiso 1 1 calc R . . . .
C6 C -0.2208(3) 0.5921(4) -0.7617(3) 0.0629(9) Uani 1 1 d . . . . .
C7 C -0.1065(3) 0.6299(3) -0.6826(3) 0.0555(7) Uani 1 1 d . . . . .
C8 C -0.0105(3) 0.6558(3) -0.6133(3) 0.0508(7) Uani 1 1 d . . . . .
C9 C 0.1012(2) 0.6909(3) -0.5285(2) 0.0459(6) Uani 1 1 d . . . . .
C10 C 0.1332(3) 0.7975(3) -0.4578(2) 0.0489(6) Uani 1 1 d . . . . .
H10 H 0.0838 0.8602 -0.4558 0.059 Uiso 1 1 calc R . . . .
C11 C 0.2508(3) 0.7931(3) -0.3916(2) 0.0491(6) Uani 1 1 d . . . . .
H11 H 0.2956 0.8528 -0.3375 0.059 Uiso 1 1 calc R . . . .
C12 C 0.2906(2) 0.6821(3) -0.4207(2) 0.0467(6) Uani 1 1 d . . . . .
C13 C 0.4035(3) 0.6284(3) -0.3689(3) 0.0480(6) Uani 1 1 d . . . . .
C14 C 0.5010(2) 0.7068(3) -0.2858(3) 0.0492(7) Uani 1 1 d . . . . .
C15 C 0.5314(3) 0.8192(4) -0.3216(3) 0.0586(8) Uani 1 1 d . . . . .
H15 H 0.4904 0.8443 -0.3958 0.070 Uiso 1 1 calc R . . . .
C16 C 0.6226(3) 0.8930(4) -0.2468(4) 0.0665(9) Uani 1 1 d . . . . .
H16 H 0.6437 0.9662 -0.2720 0.080 Uiso 1 1 calc R . . . .
C17 C 0.6831(3) 0.8608(4) -0.1354(4) 0.0689(10) Uani 1 1 d . . . . .
C18 C 0.6507(4) 0.7513(5) -0.1005(3) 0.0752(11) Uani 1 1 d . . . . .
H18 H 0.6896 0.7286 -0.0257 0.090 Uiso 1 1 calc R . . . .
C19 C 0.5609(3) 0.6739(4) -0.1750(3) 0.0654(9) Uani 1 1 d . . . . .
H19 H 0.5413 0.5996 -0.1498 0.079 Uiso 1 1 calc R . . . .
C20 C 0.7814(4) 0.9443(6) -0.0543(5) 0.1105(19) Uani 1 1 d . . . . .
H20A H 0.8411 0.9466 -0.0754 0.166 Uiso 1 1 calc GR . . . .
H20B H 0.8116 0.9091 0.0193 0.166 Uiso 1 1 calc GR . . . .
H20C H 0.7537 1.0301 -0.0553 0.166 Uiso 1 1 calc GR . . . .
C21 C 0.4188(2) 0.5040(3) -0.3948(3) 0.0501(7) Uani 1 1 d . . . . .
C22 C 0.5093(3) 0.4122(3) -0.3479(3) 0.0577(8) Uani 1 1 d . . . . .
H22 H 0.5840 0.4283 -0.2920 0.069 Uiso 1 1 calc R . . . .
C23 C 0.4686(3) 0.2971(3) -0.3983(3) 0.0577(7) Uani 1 1 d . . . . .
H23 H 0.5097 0.2203 -0.3828 0.069 Uiso 1 1 calc R . . . .
C24 C 0.3505(2) 0.3156(3) -0.4797(3) 0.0481(6) Uani 1 1 d . . . . .
C25 C 0.2592(3) 0.2315(3) -0.5530(3) 0.0468(6) Uani 1 1 d . . . . .
C26 C 0.2890(3) 0.0958(3) -0.5652(3) 0.0510(7) Uani 1 1 d . . . . .
C27 C 0.2289(3) 0.0274(3) -0.6737(3) 0.0485(6) Uani 1 1 d . . . . .
C28 C 0.2223(3) -0.1059(3) -0.6733(3) 0.0538(7) Uani 1 1 d . . . . .
H28 H 0.2511 -0.1495 -0.6059 0.065 Uiso 1 1 calc R . . . .
C29 C 0.1735(3) -0.1748(3) -0.7714(3) 0.0622(8) Uani 1 1 d . . . . .
H29 H 0.1665 -0.2639 -0.7709 0.075 Uiso 1 1 calc R . . . .
C30 C 0.1355(4) -0.1088(4) -0.8701(3) 0.0668(9) Uani 1 1 d . . . . .
C31 C 0.1429(4) 0.0233(4) -0.8726(3) 0.0701(9) Uani 1 1 d . . . . .
H31 H 0.1173 0.0663 -0.9400 0.084 Uiso 1 1 calc R . . . .
C32 C 0.1884(3) 0.0912(3) -0.7743(3) 0.0587(8) Uani 1 1 d . . . . .
H32 H 0.1919 0.1806 -0.7754 0.070 Uiso 1 1 calc R . . . .
C33 C 0.1470(2) 0.2774(3) -0.5981(2) 0.0453(6) Uani 1 1 d . . . . .
C34 C 0.0422(2) 0.1981(3) -0.6536(2) 0.0451(6) Uani 1 1 d . . . . .
C35 C 0.0352(3) 0.0771(3) -0.6131(3) 0.0497(7) Uani 1 1 d . . . . .
H35 H 0.0993 0.0429 -0.5521 0.060 Uiso 1 1 calc R . . . .
C36 C -0.0668(3) 0.0072(3) -0.6629(3) 0.0560(7) Uani 1 1 d . . . . .
H36 H -0.0712 -0.0735 -0.6357 0.067 Uiso 1 1 calc R . . . .
C37 C -0.1611(3) 0.0588(3) -0.7531(3) 0.0572(8) Uani 1 1 d . . . . .
C38 C -0.1560(3) 0.1776(4) -0.7946(3) 0.0644(9) Uani 1 1 d . . . . .
H38 H -0.2203 0.2110 -0.8559 0.077 Uiso 1 1 calc R . . . .
C39 C -0.0546(3) 0.2468(3) -0.7446(3) 0.0561(7) Uani 1 1 d . . . . .
H39 H -0.0512 0.3275 -0.7723 0.067 Uiso 1 1 calc R . . . .
B1 B 0.2117(3) 0.4987(3) -0.5621(3) 0.0456(7) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C33 O1 B1 119.9(2) . . ?
C9 N1 C12 107.5(2) . . ?
C9 N1 B1 130.9(2) . . ?
C12 N1 B1 121.3(2) . . ?
C21 N2 B1 126.8(2) . . ?
C24 N2 C21 110.2(2) . . ?
C24 N2 B1 122.7(3) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.3(7) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 121.3(4) . . ?
C5 C6 C7 119.6(4) . . ?
C8 C7 C6 176.5(4) . . ?
C7 C8 C9 177.1(3) . . ?
N1 C9 C8 122.3(3) . . ?
N1 C9 C10 109.2(3) . . ?
C10 C9 C8 128.5(3) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 C9 107.7(3) . . ?
C11 C10 H10 126.2 . . ?
C10 C11 H11 126.3 . . ?
C10 C11 C12 107.4(3) . . ?
C12 C11 H11 126.3 . . ?
N1 C12 C11 108.2(2) . . ?
N1 C12 C13 122.7(3) . . ?
C11 C12 C13 128.8(3) . . ?
C12 C13 C14 119.0(3) . . ?
C21 C13 C12 119.1(3) . . ?
C21 C13 C14 121.9(3) . . ?
C15 C14 C13 118.5(3) . . ?
C19 C14 C13 122.6(3) . . ?
C19 C14 C15 118.9(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 120.8(4) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 121.2(4) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.3(4) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 106.1(3) . . ?
C13 C21 N2 118.4(3) . . ?
C13 C21 C22 135.0(3) . . ?
C21 C22 H22 125.7 . . ?
C23 C22 C21 108.5(3) . . ?
C23 C22 H22 125.7 . . ?
C22 C23 H23 126.4 . . ?
C22 C23 C24 107.3(3) . . ?
C24 C23 H23 126.4 . . ?
N2 C24 C23 107.8(3) . . ?
N2 C24 C25 117.6(3) . . ?
C23 C24 C25 134.4(3) . . ?
C24 C25 C26 118.2(3) . . ?
C33 C25 C24 117.6(3) . . ?
C33 C25 C26 123.8(3) . . ?
O2 C26 C25 119.2(3) . . ?
O2 C26 C27 119.5(3) . . ?
C27 C26 C25 121.2(3) . . ?
C28 C27 C26 118.6(3) . . ?
C32 C27 C26 122.1(3) . . ?
C32 C27 C28 119.1(3) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C28 C29 H29 120.7 . . ?
C30 C29 C28 118.6(3) . . ?
C30 C29 H29 120.7 . . ?
C29 C30 Cl1 119.1(3) . . ?
C29 C30 C31 121.5(4) . . ?
C31 C30 Cl1 119.3(3) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.3(4) . . ?
C32 C31 H31 120.4 . . ?
C27 C32 H32 119.8 . . ?
C31 C32 C27 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
O1 C33 C25 122.4(3) . . ?
O1 C33 C34 112.2(2) . . ?
C25 C33 C34 125.3(3) . . ?
C35 C34 C33 121.6(3) . . ?
C39 C34 C33 119.8(3) . . ?
C39 C34 C35 118.5(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.6(3) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.4 . . ?
C37 C36 C35 119.2(3) . . ?
C37 C36 H36 120.4 . . ?
C36 C37 Cl2 118.4(3) . . ?
C38 C37 Cl2 120.3(3) . . ?
C38 C37 C36 121.3(3) . . ?
C37 C38 H38 120.4 . . ?
C37 C38 C39 119.3(3) . . ?
C39 C38 H38 120.4 . . ?
C34 C39 H39 119.4 . . ?
C38 C39 C34 121.1(3) . . ?
C38 C39 H39 119.4 . . ?
F1 B1 O1 108.6(3) . . ?
F1 B1 N1 109.9(2) . . ?
F1 B1 N2 112.0(3) . . ?
O1 B1 N1 114.6(2) . . ?
O1 B1 N2 106.6(2) . . ?
N2 B1 N1 105.1(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C30 1.741(4) . ?
Cl2 C37 1.739(3) . ?
F1 B1 1.389(4) . ?
O1 C33 1.329(4) . ?
O1 B1 1.463(4) . ?
O2 C26 1.216(4) . ?
N1 C9 1.359(4) . ?
N1 C12 1.391(4) . ?
N1 B1 1.539(4) . ?
N2 C21 1.388(4) . ?
N2 C24 1.336(4) . ?
N2 B1 1.516(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.397(8) . ?
C1 C6 1.370(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.321(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(6) . ?
C6 C7 1.430(5) . ?
C7 C8 1.196(5) . ?
C8 C9 1.422(5) . ?
C9 C10 1.396(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(4) . ?
C12 C13 1.423(4) . ?
C13 C14 1.489(4) . ?
C13 C21 1.379(5) . ?
C14 C15 1.396(5) . ?
C14 C19 1.376(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(6) . ?
C17 C18 1.376(6) . ?
C17 C20 1.515(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.420(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.356(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.433(4) . ?
C24 C25 1.438(4) . ?
C25 C26 1.493(4) . ?
C25 C33 1.389(4) . ?
C26 C27 1.487(5) . ?
C27 C28 1.387(4) . ?
C27 C32 1.383(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.378(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.376(5) . ?
C30 C31 1.377(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.471(4) . ?
C34 C35 1.393(4) . ?
C34 C39 1.386(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.388(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.376(5) . ?
C37 C38 1.372(5) . ?
C38 H38 0.9300 . ?
C38 C39 1.379(5) . ?
C39 H39 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C30 C31 C32 -179.0(3) . . . . ?
Cl2 C37 C38 C39 177.3(3) . . . . ?
O1 C33 C34 C35 -135.7(3) . . . . ?
O1 C33 C34 C39 40.6(4) . . . . ?
O2 C26 C27 C28 29.3(5) . . . . ?
O2 C26 C27 C32 -145.2(3) . . . . ?
N1 C9 C10 C11 1.7(3) . . . . ?
N1 C12 C13 C14 175.1(3) . . . . ?
N1 C12 C13 C21 -6.7(4) . . . . ?
N2 C21 C22 C23 -2.0(4) . . . . ?
N2 C24 C25 C26 174.0(3) . . . . ?
N2 C24 C25 C33 -13.2(4) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C2 C1 C6 C7 176.2(4) . . . . ?
C2 C3 C4 C5 -1.9(11) . . . . ?
C3 C4 C5 C6 1.1(10) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C4 C5 C6 C7 -176.9(5) . . . . ?
C6 C1 C2 C3 0.4(8) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C9 N1 C12 C11 1.0(3) . . . . ?
C9 N1 C12 C13 174.7(3) . . . . ?
C9 N1 B1 F1 77.5(4) . . . . ?
C9 N1 B1 O1 -45.1(4) . . . . ?
C9 N1 B1 N2 -161.8(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 N1 0.0(3) . . . . ?
C10 C11 C12 C13 -173.1(3) . . . . ?
C11 C12 C13 C14 -12.6(5) . . . . ?
C11 C12 C13 C21 165.6(3) . . . . ?
C12 N1 C9 C8 178.5(3) . . . . ?
C12 N1 C9 C10 -1.7(3) . . . . ?
C12 N1 B1 F1 -95.3(3) . . . . ?
C12 N1 B1 O1 142.0(3) . . . . ?
C12 N1 B1 N2 25.3(3) . . . . ?
C12 C13 C14 C15 -64.9(4) . . . . ?
C12 C13 C14 C19 114.0(4) . . . . ?
C12 C13 C21 N2 5.1(4) . . . . ?
C12 C13 C21 C22 -166.0(4) . . . . ?
C13 C14 C15 C16 -179.1(3) . . . . ?
C13 C14 C19 C18 -179.4(4) . . . . ?
C13 C21 C22 C23 169.8(4) . . . . ?
C14 C13 C21 N2 -176.8(3) . . . . ?
C14 C13 C21 C22 12.0(6) . . . . ?
C14 C15 C16 C17 -2.0(5) . . . . ?
C15 C14 C19 C18 -0.4(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C15 C16 C17 C20 -178.9(4) . . . . ?
C16 C17 C18 C19 1.0(6) . . . . ?
C17 C18 C19 C14 -1.1(6) . . . . ?
C19 C14 C15 C16 1.9(5) . . . . ?
C20 C17 C18 C19 -179.6(4) . . . . ?
C21 N2 C24 C23 -2.3(3) . . . . ?
C21 N2 C24 C25 174.1(3) . . . . ?
C21 N2 B1 F1 90.6(4) . . . . ?
C21 N2 B1 O1 -150.8(3) . . . . ?
C21 N2 B1 N1 -28.7(4) . . . . ?
C21 C13 C14 C15 117.0(4) . . . . ?
C21 C13 C14 C19 -64.0(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 N2 1.0(4) . . . . ?
C22 C23 C24 C25 -174.5(3) . . . . ?
C23 C24 C25 C26 -10.8(5) . . . . ?
C23 C24 C25 C33 162.0(3) . . . . ?
C24 N2 C21 C13 -170.8(3) . . . . ?
C24 N2 C21 C22 2.7(3) . . . . ?
C24 N2 B1 F1 -82.8(3) . . . . ?
C24 N2 B1 O1 35.8(4) . . . . ?
C24 N2 B1 N1 157.9(3) . . . . ?
C24 C25 C26 O2 32.8(4) . . . . ?
C24 C25 C26 C27 -144.3(3) . . . . ?
C24 C25 C33 O1 10.0(4) . . . . ?
C24 C25 C33 C34 -165.7(3) . . . . ?
C25 C26 C27 C28 -153.6(3) . . . . ?
C25 C26 C27 C32 31.9(4) . . . . ?
C25 C33 C34 C35 40.4(4) . . . . ?
C25 C33 C34 C39 -143.4(3) . . . . ?
C26 C25 C33 O1 -177.7(3) . . . . ?
C26 C25 C33 C34 6.6(5) . . . . ?
C26 C27 C28 C29 -176.2(3) . . . . ?
C26 C27 C32 C31 174.0(3) . . . . ?
C27 C28 C29 C30 2.5(5) . . . . ?
C28 C27 C32 C31 -0.5(5) . . . . ?
C28 C29 C30 Cl1 176.9(3) . . . . ?
C28 C29 C30 C31 -1.5(6) . . . . ?
C29 C30 C31 C32 -0.5(6) . . . . ?
C30 C31 C32 C27 1.5(6) . . . . ?
C32 C27 C28 C29 -1.6(5) . . . . ?
C33 O1 B1 F1 82.0(3) . . . . ?
C33 O1 B1 N1 -154.6(3) . . . . ?
C33 O1 B1 N2 -38.8(4) . . . . ?
C33 C25 C26 O2 -139.4(3) . . . . ?
C33 C25 C26 C27 43.5(4) . . . . ?
C33 C34 C35 C36 176.2(3) . . . . ?
C33 C34 C39 C38 -176.5(3) . . . . ?
C34 C35 C36 C37 0.0(5) . . . . ?
C35 C34 C39 C38 -0.1(5) . . . . ?
C35 C36 C37 Cl2 -177.5(2) . . . . ?
C35 C36 C37 C38 0.2(5) . . . . ?
C36 C37 C38 C39 -0.4(6) . . . . ?
C37 C38 C39 C34 0.4(6) . . . . ?
C39 C34 C35 C36 -0.1(4) . . . . ?
B1 O1 C33 C25 19.0(4) . . . . ?
B1 O1 C33 C34 -164.8(2) . . . . ?
B1 N1 C9 C8 4.8(5) . . . . ?
B1 N1 C9 C10 -175.3(3) . . . . ?
B1 N1 C12 C11 175.4(2) . . . . ?
B1 N1 C12 C13 -10.9(4) . . . . ?
B1 N2 C21 C13 15.2(5) . . . . ?
B1 N2 C21 C22 -171.3(3) . . . . ?
B1 N2 C24 C23 172.0(3) . . . . ?
B1 N2 C24 C25 -11.6(4) . . . . ?
