#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:53:33 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296422 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/30/1573076.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_1573076
loop_
_publ_author_name
'Yang, Xue-Chun'
'Wu, Feng'
'Wu, Wen-Biao'
'Zhang, Xu'
'Feng, Jian-Jun'
_publ_section_title
;
 Enantioselective dearomative formal (3+3) cycloadditions of
 bicyclobutanes with aromatic azomethine imines: access to fused
 2,3-diazabicyclo[3.1.1]heptanes.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              19488
_journal_page_last               19495
_journal_paper_doi               10.1039/d4sc06334a
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C32 H24 Br F3 N4 O2'
_chemical_formula_sum            'C32 H24 Br F3 N4 O2'
_chemical_formula_weight         633.46
_chemical_name_systematic
(R)-(9-bromo-1-(1-methyl-1H-imidazole-2-carbonyl)-3-phenyl-1,2,3,11b-tetrahydro-4H-1,3-methanopyridazino[6,1-a]isoquinolin-4-yl)(4-(trifluoromethyl)phenyl)methanone
_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_creation_date             2024-07-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.161(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8729(2)
_cell_length_b                   12.87720(10)
_cell_length_c                   10.9786(2)
_cell_measurement_reflns_used    23677
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      73.6500
_cell_measurement_theta_min      3.3690
_cell_volume                     1423.59(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  20.00   1.00    1.00    --    0.00  57.00  90.00   47
  2  ω     39.00  85.00   1.00    1.00    --    0.00  57.00  90.00   46
  3  ω    -27.00   8.00   1.00    1.00    --    0.00  57.00  30.00   35
  4  ω     31.00  82.00   1.00    1.00    --    0.00  57.00  30.00   51
  5  ω    -66.00 -15.00   1.00    1.00    --    0.00 -57.00  60.00   51
  6  ω    -24.00  25.00   1.00    1.00    --    0.00  77.00  30.00   49
  7  ω    -25.00  75.00   1.00    1.00    --    0.00  57.00 -90.00  100
  8  ω     -1.00  37.00   1.00    1.00    --    0.00  37.00  90.00   38
  9  ω    -27.00  83.00   1.00    1.00    --    0.00  37.00-150.00  110
 10  ω     -9.00  24.00   1.00    1.00    --    0.00 -57.00  60.00   33
 11  ω     63.00  94.00   1.00    1.00    --   92.10  64.00 -48.36   31
 12  ω     45.00 108.00   1.00    1.00    --   92.10 -82.00 -60.00   63
 13  ω      4.00  29.00   1.00    1.00    --   92.10 -82.00 120.00   25
 14  ω     48.00 127.00   1.00    1.00    --   92.10 -82.00 120.00   79
 15  ω     59.00  85.00   1.00    1.00    --   92.10  79.00 136.91   26
 16  ω    134.00 162.00   1.00    1.00    --   92.10  63.00 133.20   28
 17  ω     66.00 118.00   1.00    1.00    --   92.10  50.00 -84.46   52
 18  ω    112.00 179.00   1.00    1.00    --   92.10  79.00 -11.05   67
 19  ω     57.00  90.00   1.00    1.00    --   92.10  82.00  30.00   33
 20  ω    141.00 167.00   1.00    1.00    --   92.10  77.00 -90.00   26
 21  ω     58.00  84.00   1.00    1.00    --   92.10  82.00-150.00   26
 22  ω    116.00 142.00   1.00    1.00    --   92.10  82.00-150.00   26
 23  ω     59.00  91.00   1.00    1.00    --   92.10  77.00  60.00   32
 24  ω     57.00  82.00   1.00    1.00    --   92.10  82.00-120.00   25
 25  ω     57.00 100.00   1.00    1.00    --   92.10  82.00   0.00   43
 26  ω    107.00 180.00   1.00    1.00    --   92.10  82.00   0.00   73
 27  ω     59.00  84.00   1.00    1.00    --   92.10  77.00 -60.00   25
 28  ω    103.00 129.00   1.00    1.00    --   92.10  77.00 -60.00   26
 29  ω      7.00  53.00   1.00    1.00    --   92.10 -61.00 -90.00   46
 30  ω     73.00 111.00   1.00    1.00    --   92.10 -61.00 -90.00   38
 31  ω     58.00  98.00   1.00    1.00    --   92.10  79.00 -11.05   40
 32  ω     64.00  92.00   1.00    1.00    --   92.10  63.00 133.20   28
 33  ω     59.00  98.00   1.00    1.00    --   92.10  77.00 -90.00   39
 34  ω      4.00 119.00   1.00    1.00    --   92.10 -82.00  30.00  115
 35  ω     65.00  90.00   1.00    1.00    --   92.10  62.00 109.17   25
 36  ω     59.00  84.00   1.00    1.00    --   92.10  77.00 -30.00   25
 37  ω     57.00  82.00   1.00    1.00    --   92.10  82.00 120.00   25
 38  ω     57.00  83.00   1.00    1.00    --   92.10  82.00 -90.00   26
 39  ω     62.00 126.00   1.00    1.00    --   92.10  30.00 -30.00   64
 40  ω     57.00  97.00   1.00    1.00    --   92.10  82.00 150.00   40
 41  ω     66.00 131.00   1.00    1.00    --   92.10  42.00-148.03   65
 42  ω     64.00 153.00   1.00    1.00    --   92.10  61.00 150.00   89
 43  ω     57.00  83.00   1.00    1.00    --   92.10  82.00  60.00   26
 44  ω     67.00  93.00   1.00    1.00    --   92.10  45.00  60.00   26
 45  ω    120.00 159.00   1.00    1.00    --   92.10  45.00  60.00   39
 46  ω     66.00  91.00   1.00    1.00    --   92.10  58.00-156.73   25
 47  ω     59.00  84.00   1.00    1.00    --   92.10  77.00  30.00   25
 48  ω      5.00 120.00   1.00    1.00    --   92.10 -61.00  30.00  115
 49  ω     57.00  82.00   1.00    1.00    --   92.10  82.00-180.00   25
 50  ω     59.00  84.00   1.00    1.00    --   92.10  77.00-150.00   25
 51  ω     57.00  83.00   1.00    1.00    --   92.10  82.00 -60.00   26
 52  ω     57.00  82.00   1.00    1.00    --   92.10  82.00  90.00   25
 53  ω    115.00 178.00   1.00    1.00    --   92.10  64.00 -48.36   63
 54  ω    125.00 181.00   1.00    1.00    --   92.10  50.00 -84.46   56
 55  ω     64.00 182.00   1.00    1.00    --   92.10  61.00-132.12  118
 56  ω     66.00 153.00   1.00    1.00    --   92.10  45.00  90.00   87
 57  ω    156.00 181.00   1.00    1.00    --   92.10  45.00  90.00   25
 58  ω     66.00 171.00   1.00    1.00    --   92.10  45.00 120.00  105
 59  ω      5.00  76.00   1.00    1.00    --   92.10 -82.00-180.00   71
 60  ω     93.00 128.00   1.00    1.00    --   92.10 -82.00-180.00   35
 61  ω     38.00 100.00   1.00    1.00    --   92.10 -82.00 -90.00   62
 62  ω     67.00 117.00   1.00    1.00    --   92.10  46.00   2.55   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0480203000
_diffrn_orient_matrix_UB_12      -0.0679709000
_diffrn_orient_matrix_UB_13      0.0887254000
_diffrn_orient_matrix_UB_21      -0.0097318000
_diffrn_orient_matrix_UB_22      0.0971266000
_diffrn_orient_matrix_UB_23      0.0778621000
_diffrn_orient_matrix_UB_31      -0.1450008000
_diffrn_orient_matrix_UB_32      0.0160372000
_diffrn_orient_matrix_UB_33      -0.0948784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32191
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.348
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5058
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4895
_reflns_number_total             5058
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06334a2.cif
_cod_data_source_block           exp_4382_auto
_cod_depositor_comments
'Adding full bibliography for 1573075--1573076.cif.'
_cod_database_code               1573076
_shelx_shelxl_version_number     2018/3
_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   0.614
_shelx_estimated_absorpt_t_min   0.507
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_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 4.223
_oxdiff_exptl_absorpt_empirical_full_min 0.423
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
Br1 Br 0.01236(4) 0.73147(4) 0.79798(4) 0.05191(16) Uani 1 1 d . . . . .
F1 F -0.0226(3) 0.3962(2) -0.2176(2) 0.0502(7) Uani 1 1 d . . . . .
F2 F -0.0392(3) 0.26175(17) -0.1119(2) 0.0484(6) Uani 1 1 d . . . . .
F3 F -0.1312(2) 0.4037(2) -0.0907(3) 0.0558(7) Uani 1 1 d . . . . .
O1 O 0.6125(3) 0.62595(18) 0.8743(2) 0.0410(7) Uani 1 1 d . . . . .
O2 O 0.5682(2) 0.43237(18) 0.3152(2) 0.0284(5) Uani 1 1 d . . . . .
N1 N 0.3832(3) 0.58869(18) 0.4392(2) 0.0196(5) Uani 1 1 d . . . . .
N2 N 0.4898(3) 0.56452(19) 0.3995(2) 0.0203(5) Uani 1 1 d . . . . .
N3 N 0.5373(3) 0.3594(2) 0.7942(3) 0.0320(7) Uani 1 1 d . . . . .
N4 N 0.6261(3) 0.4266(2) 0.9957(3) 0.0292(6) Uani 1 1 d . . . . .
C1 C 0.5841(3) 0.4449(2) 0.8635(3) 0.0248(7) Uani 1 1 d . . . . .
C2 C 0.5501(4) 0.2845(3) 0.8844(4) 0.0404(9) Uani 1 1 d . . . . .
H2 H 0.524780 0.214094 0.863933 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6043(4) 0.3236(3) 1.0085(4) 0.0377(8) Uani 1 1 d . . . . .
H3 H 0.623289 0.286504 1.088252 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5843(3) 0.5481(2) 0.8063(3) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.5533(3) 0.5546(2) 0.6601(3) 0.0222(6) Uani 1 1 d . . . . .
C6 C 0.6371(3) 0.4848(2) 0.6048(3) 0.0229(6) Uani 1 1 d . . . . .
H6A H 0.728770 0.471477 0.667533 0.027 Uiso 1 1 calc R U . . .
H6B H 0.592340 0.419831 0.562773 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6247(3) 0.5753(2) 0.5070(3) 0.0210(6) Uani 1 1 d . . . . .
C8 C 0.4029(3) 0.5426(2) 0.5691(3) 0.0210(6) Uani 1 1 d . . . . .
H8 H 0.383253 0.466678 0.555618 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3060(3) 0.5890(2) 0.6234(3) 0.0238(7) Uani 1 1 d . . . . .
C10 C 0.2742(4) 0.5358(3) 0.7175(3) 0.0308(7) Uani 1 1 d . . . . .
H10 H 0.312018 0.469217 0.745511 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1887(4) 0.5774(3) 0.7719(4) 0.0362(8) Uani 1 1 d . . . . .
H11 H 0.167979 0.540239 0.836486 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1344(4) 0.6741(3) 0.7297(4) 0.0337(8) Uani 1 1 d . . . . .
C13 C 0.1632(3) 0.7292(3) 0.6368(3) 0.0311(7) Uani 1 1 d . . . . .
H13 H 0.124961 0.795784 0.610110 0.037 Uiso 1 1 calc R U . . .
C14 C 0.2485(3) 0.6874(2) 0.5818(3) 0.0248(7) Uani 1 1 d . . . . .
C15 C 0.2737(3) 0.7398(2) 0.4768(3) 0.0268(6) Uani 1 1 d . . . . .
H15 H 0.241912 0.808456 0.452407 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3414(3) 0.6920(2) 0.4146(3) 0.0225(6) Uani 1 1 d . . . . .
H16 H 0.362261 0.729686 0.350549 0.027 Uiso 1 1 calc R U . . .
C17 C 0.6116(3) 0.6496(2) 0.6132(3) 0.0227(6) Uani 1 1 d . . . . .
H17A H 0.697389 0.674771 0.677981 0.027 Uiso 1 1 calc R U . . .
H17B H 0.548064 0.707338 0.577488 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4721(3) 0.4823(2) 0.3124(3) 0.0214(6) Uani 1 1 d . . . . .
C19 C 0.3368(3) 0.4584(2) 0.2113(3) 0.0216(6) Uani 1 1 d . . . . .
C20 C 0.2292(4) 0.5260(2) 0.1644(3) 0.0300(7) Uani 1 1 d . . . . .
H20 H 0.235738 0.593566 0.200955 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1124(3) 0.4950(3) 0.0645(3) 0.0298(7) Uani 1 1 d . . . . .
H21 H 0.039272 0.541466 0.033055 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1020(3) 0.3963(3) 0.0103(3) 0.0252(7) Uani 1 1 d . . . . .
C23 C 0.2093(4) 0.3289(3) 0.0555(3) 0.0295(7) Uani 1 1 d . . . . .
H23 H 0.203009 0.261611 0.018197 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3250(3) 0.3599(2) 0.1547(3) 0.0255(7) Uani 1 1 d . . . . .
H24 H 0.398203 0.313456 0.185226 0.031 Uiso 1 1 calc R U . . .
C25 C 0.7303(3) 0.6003(2) 0.4534(3) 0.0230(6) Uani 1 1 d . . . . .
C26 C 0.7201(4) 0.6918(3) 0.3836(3) 0.0334(8) Uani 1 1 d . . . . .
H26 H 0.647360 0.737377 0.369921 0.040 Uiso 1 1 calc R U . . .
C27 C 0.8168(4) 0.7168(3) 0.3334(4) 0.0393(8) Uani 1 1 d . . . . .
H27 H 0.809189 0.779135 0.284855 0.047 Uiso 1 1 calc R U . . .
C28 C 0.9229(4) 0.6518(3) 0.3536(4) 0.0385(9) Uani 1 1 d . . . . .
H28 H 0.987885 0.668798 0.318462 0.046 Uiso 1 1 calc R U . . .
C29 C 0.9348(4) 0.5613(3) 0.4256(4) 0.0348(8) Uani 1 1 d . . . . .
H29 H 1.008631 0.516623 0.440711 0.042 Uiso 1 1 calc R U . . .
C30 C 0.8395(4) 0.5361(3) 0.4753(3) 0.0289(7) Uani 1 1 d . . . . .
H30 H 0.848579 0.474148 0.525013 0.035 Uiso 1 1 calc R U . . .
C31 C -0.0226(4) 0.3648(3) -0.1005(3) 0.0317(8) Uani 1 1 d . . . . .
C32 C 0.6932(5) 0.4964(4) 1.1041(4) 0.0529(12) Uani 1 1 d . . . . .
H32A H 0.780388 0.514894 1.103329 0.079 Uiso 1 1 calc R U . . .
H32B H 0.704778 0.462091 1.187346 0.079 Uiso 1 1 calc R U . . .
H32C H 0.639970 0.559460 1.094786 0.079 Uiso 1 1 calc R U . . .
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'
Br Br -0.6763 1.2805 '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
N2 N1 C8 111.7(2) . . ?
C16 N1 N2 113.2(2) . . ?
C16 N1 C8 118.9(2) . . ?
N1 N2 C7 114.1(2) . . ?
C18 N2 N1 117.4(3) . . ?
C18 N2 C7 116.9(2) . . ?
C1 N3 C2 105.1(3) . . ?
C1 N4 C32 128.8(3) . . ?
C3 N4 C1 106.0(3) . . ?
C3 N4 C32 124.9(3) . . ?
N3 C1 N4 111.6(3) . . ?
N3 C1 C4 124.6(3) . . ?
N4 C1 C4 123.7(3) . . ?
N3 C2 H2 124.6 . . ?
N3 C2 C3 110.8(3) . . ?
C3 C2 H2 124.6 . . ?
N4 C3 H3 126.8 . . ?
C2 C3 N4 106.5(3) . . ?
C2 C3 H3 126.8 . . ?
O1 C4 C1 121.6(3) . . ?
O1 C4 C5 120.5(3) . . ?
C1 C4 C5 117.8(3) . . ?
C4 C5 C6 117.0(3) . . ?
C4 C5 C8 115.5(3) . . ?
C4 C5 C17 116.1(3) . . ?
C6 C5 C8 108.5(2) . . ?
C17 C5 C6 87.3(2) . . ?
C17 C5 C8 108.9(2) . . ?
C5 C6 H6A 114.4 . . ?
C5 C6 H6B 114.4 . . ?
H6A C6 H6B 111.5 . . ?
C7 C6 C5 85.8(2) . . ?
C7 C6 H6A 114.4 . . ?
C7 C6 H6B 114.4 . . ?
N2 C7 C6 106.1(2) . . ?
N2 C7 C17 107.9(2) . . ?
N2 C7 C25 112.0(2) . . ?
C17 C7 C6 87.2(2) . . ?
C25 C7 C6 123.2(3) . . ?
C25 C7 C17 117.4(2) . . ?
N1 C8 C5 108.0(2) . . ?
N1 C8 H8 107.6 . . ?
N1 C8 C9 110.6(2) . . ?
C5 C8 H8 107.6 . . ?
C9 C8 C5 115.1(2) . . ?
C9 C8 H8 107.6 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 C14 118.7(3) . . ?
C14 C9 C8 121.0(3) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.7(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 Br1 119.4(3) . . ?
C13 C12 Br1 118.7(3) . . ?
C13 C12 C11 121.9(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C15 118.9(3) . . ?
C13 C14 C9 119.6(3) . . ?
C13 C14 C15 121.5(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
N1 C16 H16 118.5 . . ?
C15 C16 N1 123.0(3) . . ?
C15 C16 H16 118.5 . . ?
C5 C17 C7 85.9(2) . . ?
C5 C17 H17A 114.3 . . ?
C5 C17 H17B 114.3 . . ?
C7 C17 H17A 114.3 . . ?
C7 C17 H17B 114.3 . . ?
H17A C17 H17B 111.5 . . ?
O2 C18 N2 119.3(3) . . ?
O2 C18 C19 120.2(3) . . ?
N2 C18 C19 120.5(3) . . ?
C20 C19 C18 126.7(3) . . ?
C20 C19 C24 118.6(3) . . ?
C24 C19 C18 114.5(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C31 119.9(3) . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 C31 120.2(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.3(3) . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C7 118.8(3) . . ?
C26 C25 C30 119.1(3) . . ?
C30 C25 C7 122.1(3) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.7(3) . . ?
C29 C30 H30 119.6 . . ?
F1 C31 C22 111.7(3) . . ?
F2 C31 F1 104.9(3) . . ?
F2 C31 C22 113.2(3) . . ?
F3 C31 F1 106.5(3) . . ?
F3 C31 F2 106.8(3) . . ?
F3 C31 C22 113.2(3) . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
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
Br1 C12 1.903(4) . ?
F1 C31 1.347(4) . ?
F2 C31 1.339(4) . ?
F3 C31 1.324(5) . ?
O1 C4 1.218(4) . ?
O2 C18 1.217(4) . ?
N1 N2 1.418(4) . ?
N1 C8 1.484(4) . ?
N1 C16 1.399(4) . ?
N2 C7 1.502(4) . ?
N2 C18 1.391(4) . ?
N3 C1 1.326(4) . ?
N3 C2 1.351(5) . ?
N4 C1 1.369(4) . ?
N4 C3 1.363(5) . ?
N4 C32 1.449(5) . ?
C1 C4 1.469(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.514(4) . ?
C5 C6 1.556(4) . ?
C5 C8 1.570(4) . ?
C5 C17 1.553(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.556(4) . ?
C7 C17 1.556(4) . ?
C7 C25 1.509(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(4) . ?
C9 C10 1.388(5) . ?
C9 C14 1.410(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(6) . ?
C12 C13 1.371(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(5) . ?
C14 C15 1.449(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.328(4) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.503(4) . ?
C19 C20 1.392(5) . ?
C19 C24 1.397(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(5) . ?
C22 C23 1.387(5) . ?
C22 C31 1.495(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(5) . ?
C25 C30 1.392(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.397(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.373(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.379(5) . ?
C30 H30 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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
Br1 C12 C13 C14 -177.7(2) . . . . ?
O1 C4 C5 C6 124.5(4) . . . . ?
O1 C4 C5 C8 -105.9(4) . . . . ?
O1 C4 C5 C17 23.5(5) . . . . ?
O2 C18 C19 C20 -156.0(3) . . . . ?
O2 C18 C19 C24 19.3(4) . . . . ?
N1 N2 C7 C6 70.5(3) . . . . ?
N1 N2 C7 C17 -21.8(3) . . . . ?
N1 N2 C7 C25 -152.4(2) . . . . ?
N1 N2 C18 O2 -150.9(3) . . . . ?
N1 N2 C18 C19 32.1(4) . . . . ?
N1 C8 C9 C10 158.1(3) . . . . ?
N1 C8 C9 C14 -23.3(4) . . . . ?
N2 N1 C8 C5 40.3(3) . . . . ?
N2 N1 C8 C9 167.0(2) . . . . ?
N2 N1 C16 C15 -159.1(3) . . . . ?
N2 C7 C17 C5 78.4(2) . . . . ?
N2 C7 C25 C26 61.6(4) . . . . ?
N2 C7 C25 C30 -120.4(3) . . . . ?
N2 C18 C19 C20 21.0(5) . . . . ?
N2 C18 C19 C24 -163.7(3) . . . . ?
N3 C1 C4 O1 170.3(4) . . . . ?
N3 C1 C4 C5 -12.0(5) . . . . ?
N3 C2 C3 N4 0.1(5) . . . . ?
N4 C1 C4 O1 -6.0(5) . . . . ?
N4 C1 C4 C5 171.7(3) . . . . ?
C1 N3 C2 C3 0.1(5) . . . . ?
C1 N4 C3 C2 -0.2(4) . . . . ?
C1 C4 C5 C6 -53.2(4) . . . . ?
C1 C4 C5 C8 76.4(4) . . . . ?
C1 C4 C5 C17 -154.2(3) . . . . ?
C2 N3 C1 N4 -0.2(4) . . . . ?
C2 N3 C1 C4 -176.9(3) . . . . ?
C3 N4 C1 N3 0.3(4) . . . . ?
C3 N4 C1 C4 177.0(3) . . . . ?
C4 C5 C6 C7 -145.6(3) . . . . ?
C4 C5 C8 N1 159.2(2) . . . . ?
C4 C5 C8 C9 35.1(4) . . . . ?
C4 C5 C17 C7 146.4(3) . . . . ?
C5 C6 C7 N2 -80.3(2) . . . . ?
C5 C6 C7 C17 27.5(2) . . . . ?
C5 C6 C7 C25 148.7(3) . . . . ?
C5 C8 C9 C10 -79.2(4) . . . . ?
C5 C8 C9 C14 99.4(3) . . . . ?
C6 C5 C8 N1 -67.2(3) . . . . ?
C6 C5 C8 C9 168.8(2) . . . . ?
C6 C5 C17 C7 27.6(2) . . . . ?
C6 C7 C17 C5 -27.6(2) . . . . ?
C6 C7 C25 C26 -170.0(3) . . . . ?
C6 C7 C25 C30 8.0(4) . . . . ?
C7 N2 C18 O2 -9.8(4) . . . . ?
C7 N2 C18 C19 173.2(3) . . . . ?
C7 C25 C26 C27 179.8(3) . . . . ?
C7 C25 C30 C29 -179.7(3) . . . . ?
C8 N1 N2 C7 -43.8(3) . . . . ?
C8 N1 N2 C18 98.3(3) . . . . ?
C8 N1 C16 C15 -25.0(4) . . . . ?
C8 C5 C6 C7 81.5(3) . . . . ?
C8 C5 C17 C7 -81.1(3) . . . . ?
C8 C9 C10 C11 178.2(3) . . . . ?
C8 C9 C14 C13 -177.9(3) . . . . ?
C8 C9 C14 C15 5.8(4) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C9 C14 C15 C16 5.1(5) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C10 C9 C14 C15 -175.6(3) . . . . ?
C10 C11 C12 Br1 178.0(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C9 -0.8(5) . . . . ?
C12 C13 C14 C15 175.5(3) . . . . ?
C13 C14 C15 C16 -171.1(3) . . . . ?
C14 C9 C10 C11 -0.5(5) . . . . ?
C14 C15 C16 N1 4.5(5) . . . . ?
C16 N1 N2 C7 93.6(3) . . . . ?
C16 N1 N2 C18 -124.3(3) . . . . ?
C16 N1 C8 C5 -94.5(3) . . . . ?
C16 N1 C8 C9 32.3(4) . . . . ?
C17 C5 C6 C7 -27.6(2) . . . . ?
C17 C5 C8 N1 26.4(3) . . . . ?
C17 C5 C8 C9 -97.6(3) . . . . ?
C17 C7 C25 C26 -64.1(4) . . . . ?
C17 C7 C25 C30 113.9(3) . . . . ?
C18 N2 C7 C6 -71.8(3) . . . . ?
C18 N2 C7 C17 -164.1(2) . . . . ?
C18 N2 C7 C25 65.2(3) . . . . ?
C18 C19 C20 C21 175.9(3) . . . . ?
C18 C19 C24 C23 -176.4(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C19 C24 C23 -0.8(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C20 C21 C22 C31 -177.9(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C21 C22 C31 F1 84.3(4) . . . . ?
C21 C22 C31 F2 -157.6(3) . . . . ?
C21 C22 C31 F3 -35.9(5) . . . . ?
C22 C23 C24 C19 0.1(5) . . . . ?
C23 C22 C31 F1 -92.9(4) . . . . ?
C23 C22 C31 F2 25.2(5) . . . . ?
C23 C22 C31 F3 146.9(3) . . . . ?
C24 C19 C20 C21 0.8(5) . . . . ?
C25 C7 C17 C5 -153.9(3) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
C26 C25 C30 C29 -1.7(5) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C28 C29 C30 0.8(6) . . . . ?
C28 C29 C30 C25 0.4(5) . . . . ?
C30 C25 C26 C27 1.7(5) . . . . ?
C31 C22 C23 C24 177.9(3) . . . . ?
C32 N4 C1 N3 174.2(4) . . . . ?
C32 N4 C1 C4 -9.0(6) . . . . ?
C32 N4 C3 C2 -174.5(4) . . . . ?
