#------------------------------------------------------------------------------
#$Date: 2025-10-17 03:53:23 +0300 (Fri, 17 Oct 2025) $
#$Revision: 302945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/40/7064072.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_7064072
loop_
_publ_author_name
'Prasannan, Dijo'
'Nemykin, Viktor N.'
_publ_section_title
;
 Unexpected Formation of α-Formylated BOPHY in the Reaction with Copper
 Salts
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ02748A
_journal_year                    2025
_chemical_formula_moiety         '2(C21 H19 B Br F2 N5)'
_chemical_formula_sum            'C42 H38 B2 Br2 F4 N10'
_chemical_formula_weight         940.26
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                98.094(6)
_cell_angle_beta                 93.490(6)
_cell_angle_gamma                118.563(5)
_cell_formula_units_Z            2
_cell_length_a                   13.1933(14)
_cell_length_b                   13.3860(13)
_cell_length_c                   13.7640(14)
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      50.32
_cell_measurement_theta_min      5.19
_cell_volume                     2090.6(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9642
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        50.538
_diffrn_reflns_theta_max         50.538
_diffrn_reflns_theta_min         5.190
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.985
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.4755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1291 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.6340.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.017
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         4192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0957
_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)+(0.0851P)²+15.7737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3007
_reflns_number_total             4192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj02748a2.cif
_cod_data_source_block           cu_dijo_bophy_alkyne_0m_a
_cod_database_code               7064072
_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   0.951
_shelx_estimated_absorpt_t_min   0.581
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C1) = Uanis(C2) = Uanis(C4)
Uanis(C18) = Uanis(C7) = Uanis(C8) = Uanis(C9)
Uanis(C26) = Uanis(C12) = Uanis(C8) = Uanis(C15)
Uanis(C34) = Uanis(C30) = Uanis(C37) = Uanis(C38) = Uanis(C29)
Uanis(C17) = Uanis(C36)
Uanis(B2) = Uanis(B1)
Uanis(F5) = Uanis(F4) = Uanis(F2) = Uanis(F1)
Uanis(N7) = Uanis(N4) = Uanis(N3)
Uanis(N6) = Uanis(N4) = Uanis(N3) = Uanis(N2) = Uanis(N7) = Uanis(N8)
Uanis(Br2) = Uanis(Br4)
3. Others
 Sof(H38)=Sof(Br4)=1-FVAR(1)
 Sof(H34)=Sof(Br2)=FVAR(1)
 Sof(H11)=Sof(Br3)=1-FVAR(2)
 Sof(H17)=Sof(Br1)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C17(H17), C31(H31),
 C34(H34), C38(H38), N5(H5A), N10(H10)
4.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0689(11) 0.4100(10) 0.6325(9) 0.0381(16) Uani 1 1 d . . . . .
C2 C 0.1493(11) 0.5268(10) 0.6591(9) 0.0381(16) Uani 1 1 d . . . . .
H2 H 0.229132 0.552152 0.680529 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1116(11) 0.6048(11) 0.6540(9) 0.043(3) Uani 1 1 d . . . . .
H3 H 0.168250 0.684767 0.670149 0.052 Uiso 1 1 calc R U . . .
C4 C -0.0769(11) 0.4652(11) 0.6050(9) 0.0381(16) Uani 1 1 d . . . . .
H4 H -0.156291 0.443672 0.586547 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0486(11) 0.3789(11) 0.6066(9) 0.045(3) Uani 1 1 d . . . . .
H5 H -0.107454 0.299696 0.590447 0.054 Uiso 1 1 calc R U . . .
C6 C 0.0995(10) 0.3198(11) 0.6383(8) 0.038(3) Uani 1 1 d . . . . .
C7 C 0.1247(10) 0.2442(11) 0.6373(9) 0.0354(12) Uani 1 1 d . . . . .
C8 C 0.1462(10) 0.1496(10) 0.6327(8) 0.0354(12) Uani 1 1 d . . . . .
C9 C 0.2595(10) 0.1669(10) 0.6389(9) 0.0354(12) Uani 1 1 d . . . . .
C10 C 0.3694(10) 0.2664(9) 0.6544(8) 0.032(3) Uani 1 1 d . . . . .
C11 C 0.4508(10) 0.2298(11) 0.6547(9) 0.043(3) Uani 1 1 d . . . . .
H11 H 0.533029 0.279046 0.664301 0.052 Uiso 0.174(4) 1 calc R U P A 1
C12 C 0.3926(10) 0.1072(10) 0.6383(9) 0.0354(12) Uani 1 1 d . . . . .
C13 C 0.3985(10) 0.3921(10) 0.6645(10) 0.044(3) Uani 1 1 d . . . . .
H13A H 0.383643 0.407397 0.599123 0.065 Uiso 1 1 calc R U . . .
H13B H 0.480948 0.443015 0.692264 0.065 Uiso 1 1 calc R U . . .
H13C H 0.349734 0.406906 0.708795 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0367(10) -0.1513(10) 0.6116(8) 0.035(3) Uani 1 1 d . . . . .
H14 H -0.027175 -0.217673 0.607397 0.042 Uiso 1 1 calc R U . . .
C15 C -0.1489(10) -0.1706(10) 0.6105(9) 0.0354(12) Uani 1 1 d . . . . .
C16 C -0.2507(10) -0.2783(10) 0.6005(9) 0.039(3) Uani 1 1 d . . . . .
C17 C -0.3446(11) -0.2612(11) 0.6010(9) 0.039(2) Uani 1 1 d . . . . .
H17 H -0.423814 -0.320153 0.594581 0.047 Uiso 0.826(4) 1 calc R U P A 2
C18 C -0.3044(10) -0.1414(10) 0.6125(9) 0.0354(12) Uani 1 1 d . . . . .
C19 C 0.4392(10) 0.0259(11) 0.6279(9) 0.046(3) Uani 1 1 d . . . . .
H19A H 0.523540 0.069200 0.627338 0.069 Uiso 1 1 calc R U . . .
H19B H 0.401298 -0.030682 0.565661 0.069 Uiso 1 1 calc R U . . .
H19C H 0.423511 -0.014702 0.683828 0.069 Uiso 1 1 calc R U . . .
C20 C -0.2531(11) -0.3934(10) 0.5872(9) 0.045(3) Uani 1 1 d . . . . .
H20A H -0.241209 -0.414055 0.519276 0.067 Uiso 1 1 calc R U . . .
H20B H -0.328743 -0.453360 0.599309 0.067 Uiso 1 1 calc R U . . .
H20C H -0.190786 -0.387553 0.634257 0.067 Uiso 1 1 calc R U . . .
C21 C -0.3688(10) -0.0767(10) 0.6212(9) 0.040(3) Uani 1 1 d . . . . .
H21A H -0.443335 -0.120645 0.576772 0.060 Uiso 1 1 calc R U . . .
H21B H -0.322445 -0.001118 0.602930 0.060 Uiso 1 1 calc R U . . .
H21C H -0.383294 -0.065394 0.689816 0.060 Uiso 1 1 calc R U . . .
C22 C 1.3944(10) 1.0523(10) 0.8821(8) 0.034(3) Uani 1 1 d . . . . .
C23 C 1.5128(11) 1.1350(11) 0.8812(9) 0.0381(16) Uani 1 1 d . . . . .
H23 H 1.519(9) 1.217(10) 0.881(8) 0.046 Uiso 1 1 d . U . . .
C24 C 1.5896(11) 1.0951(12) 0.8728(9) 0.046(4) Uani 1 1 d . . . . .
H24 H 1.672(11) 1.163(10) 0.886(8) 0.055 Uiso 1 1 d . U . . .
C25 C 1.4535(12) 0.9107(11) 0.8703(10) 0.042(4) Uani 1 1 d . . . . .
H25 H 1.439(10) 0.840(11) 0.866(9) 0.050 Uiso 1 1 d . U . . .
C26 C 1.3667(11) 0.9385(11) 0.8761(9) 0.0354(12) Uani 1 1 d . . . . .
H26 H 1.288(9) 0.881(9) 0.882(7) 0.043 Uiso 1 1 d . U . . .
C27 C 1.3028(12) 1.0829(10) 0.8859(9) 0.039(3) Uani 1 1 d . . . . .
C28 C 1.2255(12) 1.1079(10) 0.8859(9) 0.040(3) Uani 1 1 d . . . . .
C29 C 1.1273(10) 1.1249(10) 0.8818(8) 0.0322(14) Uani 1 1 d . . . . .
C30 C 1.1422(10) 1.2382(9) 0.8846(8) 0.0322(14) Uani 1 1 d . . . . .
C31 C 0.8272(10) 0.9420(9) 0.8662(8) 0.034(3) Uani 1 1 d . . . . .
H31 H 0.759141 0.949688 0.865207 0.041 Uiso 1 1 calc R U . . .
C32 C 0.8097(10) 0.8285(11) 0.8616(8) 0.036(3) Uani 1 1 d . . . . .
C33 C 0.8408(11) 0.6785(11) 0.8598(9) 0.041(3) Uani 1 1 d . . . . .
C34 C 0.7229(10) 0.6373(10) 0.8499(8) 0.0322(14) Uani 1 1 d . . . . .
H34 H 0.665378 0.558098 0.842892 0.039 Uiso 0.927(2) 1 calc R U P B 2
C35 C 0.6995(10) 0.7288(10) 0.8517(8) 0.034(3) Uani 1 1 d . . . . .
C36 C 1.0825(11) 1.3672(11) 0.8858(9) 0.039(2) Uani 1 1 d . . . . .
C37 C 1.2427(10) 1.3458(9) 0.8982(8) 0.0322(14) Uani 1 1 d . . . . .
C38 C 1.2017(10) 1.4244(10) 0.8995(8) 0.0322(14) Uani 1 1 d . . . . .
H38 H 1.249684 1.506107 0.908609 0.039 Uiso 0.073(2) 1 calc R U P B 1
C39 C 0.9976(10) 1.4115(10) 0.8800(9) 0.043(3) Uani 1 1 d . . . . .
H39A H 0.958720 1.401720 0.939220 0.065 Uiso 1 1 calc R U . . .
H39B H 0.939132 1.367905 0.820716 0.065 Uiso 1 1 calc R U . . .
H39C H 1.039391 1.493923 0.876370 0.065 Uiso 1 1 calc R U . . .
C40 C 0.9115(11) 0.6180(11) 0.8596(8) 0.040(3) Uani 1 1 d . . . . .
H40A H 0.869908 0.546889 0.885963 0.060 Uiso 1 1 calc R U . . .
H40B H 0.987256 0.669187 0.901214 0.060 Uiso 1 1 calc R U . . .
H40C H 0.923662 0.598364 0.791612 0.060 Uiso 1 1 calc R U . . .
C41 C 0.5852(10) 0.7228(10) 0.8444(9) 0.045(3) Uani 1 1 d . . . . .
H41A H 0.575633 0.756129 0.908931 0.068 Uiso 1 1 calc R U . . .
H41B H 0.523553 0.641639 0.824685 0.068 Uiso 1 1 calc R U . . .
H41C H 0.580144 0.766522 0.794676 0.068 Uiso 1 1 calc R U . . .
C42 C 1.3683(9) 1.3763(10) 0.9121(9) 0.040(3) Uani 1 1 d . . . . .
H42A H 1.389501 1.366716 0.978209 0.061 Uiso 1 1 calc R U . . .
H42B H 1.417202 1.457021 0.905440 0.061 Uiso 1 1 calc R U . . .
H42C H 1.380288 1.325111 0.861593 0.061 Uiso 1 1 calc R U . . .
B1 B 0.1821(13) -0.0574(14) 0.6031(10) 0.046(3) Uani 1 1 d . . . . .
B2 B 0.9212(13) 1.1568(13) 0.8687(10) 0.046(3) Uani 1 1 d . . . . .
Br1 Br 0.61372(13) 0.31895(13) 0.67548(13) 0.0459(7) Uani 0.826(4) 1 d . . P A 2
Br2 Br 1.29145(12) 1.58827(12) 0.92615(11) 0.0465(6) Uani 0.927(2) 1 d . . P B 2
F1 F 0.1710(6) -0.1053(6) 0.5116(6) 0.0547(11) Uani 1 1 d . . . . .
F2 F 0.1881(6) -0.1190(6) 0.6716(6) 0.0547(11) Uani 1 1 d . . . . .
F4 F 0.8547(6) 1.1428(6) 0.7888(6) 0.0547(11) Uani 1 1 d . . . . .
F5 F 0.8690(6) 1.1722(6) 0.9519(6) 0.0547(11) Uani 1 1 d . . . . .
N1 N 0.0017(9) 0.5773(9) 0.6281(7) 0.040(3) Uani 1 1 d . . . . .
N2 N 0.2781(8) 0.0720(8) 0.6299(7) 0.0353(11) Uani 1 1 d . . . . .
N3 N 0.0609(8) -0.0496(8) 0.6179(7) 0.0353(11) Uani 1 1 d . . . . .
N4 N 0.0487(8) 0.0485(8) 0.6232(7) 0.0353(11) Uani 1 1 d . . . . .
N5 N -0.1866(8) -0.0888(8) 0.6190(6) 0.035(2) Uani 1 1 d . . . . .
H5A H -0.140259 -0.013350 0.627413 0.042 Uiso 1 1 calc R U . . .
N6 N 1.5640(9) 0.9846(9) 0.8684(7) 0.0353(11) Uani 1 1 d . . . . .
N7 N 1.0285(8) 1.0289(8) 0.8762(7) 0.0353(11) Uani 1 1 d . . . . .
N8 N 0.9286(8) 1.0402(8) 0.8717(7) 0.0353(11) Uani 1 1 d . . . . .
N9 N 1.0456(7) 1.2523(7) 0.8782(7) 0.030(2) Uani 1 1 d . . . . .
N10 N 0.8942(9) 0.7967(9) 0.8653(7) 0.038(3) Uani 1 1 d . . . . .
H10 H 0.969799 0.843857 0.870407 0.045 Uiso 1 1 calc R U . . .
Br3 Br -0.4976(6) -0.3522(6) 0.5792(5) 0.037(3) Uani 0.174(4) 1 d . . P A 1
Br4 Br 0.6555(16) 0.4964(15) 0.8407(14) 0.0465(6) Uani 0.073(2) 1 d . . P B 1
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0350
-1.00 1.00 1.00 0.0320
-1.00 -1.00 0.00 0.0030
-1.00 1.00 0.00 0.0160
0.00 0.00 -1.00 0.0980
1.00 1.00 0.00 0.0050
1.00 -1.00 0.00 0.0050
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
C2 C1 C5 117.6(11) . . ?
C2 C1 C6 122.8(11) . . ?
C5 C1 C6 119.5(11) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.4(12) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 117.6 . . ?
N1 C3 C2 124.9(12) . . ?
N1 C3 H3 117.6 . . ?
C5 C4 H4 118.5 . . ?
N1 C4 H4 118.5 . . ?
N1 C4 C5 123.0(12) . . ?
C1 C5 H5 120.6 . . ?
C4 C5 C1 118.9(12) . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C1 176.3(12) . . ?
C6 C7 C8 175.9(13) . . ?
C9 C8 C7 121.1(11) . . ?
N4 C8 C7 112.5(10) . . ?
N4 C8 C9 126.4(11) . . ?
C8 C9 C10 133.1(11) . . ?
C8 C9 N2 120.0(10) . . ?
N2 C9 C10 107.0(9) . . ?
C9 C10 C13 128.5(10) . . ?
C11 C10 C9 106.9(10) . . ?
C11 C10 C13 124.5(11) . . ?
C10 C11 H11 125.4 . . ?
C10 C11 C12 109.2(11) . . ?
C10 C11 Br1 128.8(10) . . ?
C12 C11 H11 125.4 . . ?
C12 C11 Br1 121.9(9) . . ?
C11 C12 C19 130.6(11) . . ?
N2 C12 C11 106.3(10) . . ?
N2 C12 C19 123.1(11) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 H14 116.2 . . ?
N3 C14 H14 116.2 . . ?
N3 C14 C15 127.5(11) . . ?
C14 C15 C16 126.8(11) . . ?
C14 C15 N5 128.0(11) . . ?
N5 C15 C16 105.3(10) . . ?
C15 C16 C20 124.3(10) . . ?
C17 C16 C15 109.0(11) . . ?
C17 C16 C20 126.7(11) . . ?
C16 C17 H17 125.8 . . ?
C16 C17 C18 108.4(11) . . ?
C16 C17 Br3 135.2(10) . . ?
C18 C17 H17 125.8 . . ?
C18 C17 Br3 116.0(9) . . ?
C17 C18 C21 130.5(11) . . ?
N5 C18 C17 106.6(10) . . ?
N5 C18 C21 122.9(10) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 122.7(11) . . ?
C26 C22 C23 117.7(11) . . ?
C26 C22 C27 119.6(11) . . ?
C22 C23 H23 109(6) . . ?
C24 C23 C22 117.3(12) . . ?
C24 C23 H23 134(6) . . ?
C23 C24 H24 110(7) . . ?
N6 C24 C23 125.5(12) . . ?
N6 C24 H24 124(7) . . ?
C26 C25 H25 121(8) . . ?
N6 C25 H25 113(8) . . ?
N6 C25 C26 125.3(12) . . ?
C22 C26 H26 120(6) . . ?
C25 C26 C22 118.9(12) . . ?
C25 C26 H26 121(6) . . ?
C28 C27 C22 178.0(13) . . ?
C27 C28 C29 174.1(13) . . ?
C28 C29 C30 120.3(10) . . ?
N7 C29 C28 113.1(10) . . ?
N7 C29 C30 126.6(10) . . ?
C37 C30 C29 131.0(10) . . ?
N9 C30 C29 119.3(10) . . ?
N9 C30 C37 109.6(9) . . ?
C32 C31 H31 116.2 . . ?
N8 C31 H31 116.2 . . ?
N8 C31 C32 127.6(11) . . ?
C35 C32 C31 124.2(11) . . ?
N10 C32 C31 126.8(11) . . ?
N10 C32 C35 109.0(10) . . ?
C34 C33 C40 131.8(11) . . ?
C34 C33 N10 107.4(10) . . ?
N10 C33 C40 120.6(11) . . ?
C33 C34 H34 124.9 . . ?
C33 C34 C35 110.1(10) . . ?
C33 C34 Br4 109.2(11) . . ?
C35 C34 H34 124.9 . . ?
C35 C34 Br4 140.7(12) . . ?
C32 C35 C41 127.4(11) . . ?
C34 C35 C32 104.9(10) . . ?
C34 C35 C41 127.7(11) . . ?
C38 C36 C39 131.0(11) . . ?
N9 C36 C38 107.6(10) . . ?
N9 C36 C39 121.4(11) . . ?
C30 C37 C38 104.4(10) . . ?
C30 C37 C42 129.9(10) . . ?
C38 C37 C42 125.7(10) . . ?
C36 C38 C37 110.3(10) . . ?
C36 C38 H38 124.9 . . ?
C36 C38 Br2 122.3(9) . . ?
C37 C38 H38 124.9 . . ?
C37 C38 Br2 127.2(9) . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C33 C40 H40A 109.5 . . ?
C33 C40 H40B 109.5 . . ?
C33 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C35 C41 H41A 109.5 . . ?
C35 C41 H41B 109.5 . . ?
C35 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
F1 B1 F2 115.1(14) . . ?
F1 B1 N2 113.8(11) . . ?
F1 B1 N3 107.6(10) . . ?
F2 B1 N2 112.5(10) . . ?
F2 B1 N3 104.1(10) . . ?
N2 B1 N3 102.1(11) . . ?
F4 B2 F5 108.9(13) . . ?
F4 B2 N8 110.0(11) . . ?
F4 B2 N9 114.9(11) . . ?
F5 B2 N8 105.8(10) . . ?
F5 B2 N9 111.4(10) . . ?
N9 B2 N8 105.5(11) . . ?
C3 N1 C4 117.1(10) . . ?
C9 N2 B1 125.9(10) . . ?
C12 N2 C9 110.6(9) . . ?
C12 N2 B1 123.3(10) . . ?
C14 N3 B1 115.6(10) . . ?
C14 N3 N4 117.1(9) . . ?
N4 N3 B1 126.8(9) . . ?
C8 N4 N3 116.8(9) . . ?
C15 N5 H5A 124.6 . . ?
C18 N5 C15 110.7(9) . . ?
C18 N5 H5A 124.6 . . ?
C25 N6 C24 115.3(10) . . ?
C29 N7 N8 115.7(9) . . ?
C31 N8 B2 116.7(9) . . ?
C31 N8 N7 115.9(9) . . ?
N7 N8 B2 127.4(9) . . ?
C30 N9 B2 125.4(10) . . ?
C36 N9 C30 108.1(9) . . ?
C36 N9 B2 126.4(11) . . ?
C32 N10 C33 108.5(10) . . ?
C32 N10 H10 125.8 . . ?
C33 N10 H10 125.8 . . ?
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
C1 C2 1.382(16) . ?
C1 C5 1.407(16) . ?
C1 C6 1.456(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(15) . ?
C3 H3 0.9500 . ?
C3 N1 1.324(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(16) . ?
C4 N1 1.329(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.205(15) . ?
C7 C8 1.418(16) . ?
C8 C9 1.394(15) . ?
C8 N4 1.330(14) . ?
C9 C10 1.399(16) . ?
C9 N2 1.396(14) . ?
C10 C11 1.378(16) . ?
C10 C13 1.518(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.416(16) . ?
C11 Br1 1.871(12) . ?
C12 C19 1.479(16) . ?
C12 N2 1.342(14) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.375(15) . ?
C14 N3 1.340(14) . ?
C15 C16 1.404(16) . ?
C15 N5 1.398(14) . ?
C16 C17 1.364(16) . ?
C16 C20 1.512(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.408(16) . ?
C17 Br3 1.766(14) . ?
C18 C21 1.474(15) . ?
C18 N5 1.356(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.421(16) . ?
C22 C26 1.374(16) . ?
C22 C27 1.451(18) . ?
C23 H23 1.06(11) . ?
C23 C24 1.357(17) . ?
C24 H24 1.01(12) . ?
C24 N6 1.342(15) . ?
C25 H25 0.86(12) . ?
C25 C26 1.365(17) . ?
C25 N6 1.319(15) . ?
C26 H26 0.97(11) . ?
C27 C28 1.217(16) . ?
C28 C29 1.417(18) . ?
C29 C30 1.427(15) . ?
C29 N7 1.309(14) . ?
C30 C37 1.391(15) . ?
C30 N9 1.374(13) . ?
C31 H31 0.9500 . ?
C31 C32 1.415(16) . ?
C31 N8 1.342(13) . ?
C32 C35 1.408(16) . ?
C32 N10 1.372(14) . ?
C33 C34 1.370(16) . ?
C33 C40 1.499(16) . ?
C33 N10 1.379(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.397(15) . ?
C34 Br4 1.64(2) . ?
C35 C41 1.466(15) . ?
C36 C38 1.365(16) . ?
C36 C39 1.501(16) . ?
C36 N9 1.358(14) . ?
C37 C38 1.392(15) . ?
C37 C42 1.497(15) . ?
C38 H38 0.9500 . ?
C38 Br2 1.893(11) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
B1 F1 1.296(15) . ?
B1 F2 1.360(16) . ?
B1 N2 1.551(17) . ?
B1 N3 1.674(19) . ?
B2 F4 1.297(15) . ?
B2 F5 1.411(16) . ?
B2 N8 1.615(19) . ?
B2 N9 1.506(17) . ?
N3 N4 1.390(12) . ?
N5 H5A 0.8800 . ?
N7 N8 1.396(12) . ?
N10 H10 0.8800 . ?
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
C1 C2 C3 N1 2.3(19) . . . . ?
C2 C1 C5 C4 2.6(17) . . . . ?
C2 C3 N1 C4 -0.4(18) . . . . ?
C5 C1 C2 C3 -3.3(17) . . . . ?
C5 C4 N1 C3 -0.3(17) . . . . ?
C6 C1 C2 C3 -178.0(11) . . . . ?
C6 C1 C5 C4 177.6(11) . . . . ?
C7 C8 C9 C10 3(2) . . . . ?
C7 C8 C9 N2 -177.3(10) . . . . ?
C7 C8 N4 N3 179.9(9) . . . . ?
C8 C9 C10 C11 179.2(13) . . . . ?
C8 C9 C10 C13 -3(2) . . . . ?
C8 C9 N2 C12 -179.9(11) . . . . ?
C8 C9 N2 B1 6.0(17) . . . . ?
C9 C8 N4 N3 -0.9(17) . . . . ?
C9 C10 C11 C12 0.7(14) . . . . ?
C9 C10 C11 Br1 -177.9(9) . . . . ?
C10 C9 N2 C12 -0.4(13) . . . . ?
C10 C9 N2 B1 -174.4(10) . . . . ?
C10 C11 C12 C19 177.2(12) . . . . ?
C10 C11 C12 N2 -0.9(14) . . . . ?
C11 C12 N2 C9 0.7(13) . . . . ?
C11 C12 N2 B1 175.0(10) . . . . ?
C13 C10 C11 C12 -176.8(11) . . . . ?
C13 C10 C11 Br1 4.6(18) . . . . ?
C14 C15 C16 C17 -178.8(12) . . . . ?
C14 C15 C16 C20 -1(2) . . . . ?
C14 C15 N5 C18 178.7(12) . . . . ?
C14 N3 N4 C8 177.9(10) . . . . ?
C15 C14 N3 B1 -172.7(11) . . . . ?
C15 C14 N3 N4 -0.5(17) . . . . ?
C15 C16 C17 C18 -0.7(14) . . . . ?
C15 C16 C17 Br3 172.0(11) . . . . ?
C16 C15 N5 C18 -1.3(13) . . . . ?
C16 C17 C18 C21 -177.5(12) . . . . ?
C16 C17 C18 N5 -0.1(13) . . . . ?
C17 C18 N5 C15 0.9(13) . . . . ?
C19 C12 N2 C9 -177.5(11) . . . . ?
C19 C12 N2 B1 -3.3(17) . . . . ?
C20 C16 C17 C18 -178.2(11) . . . . ?
C20 C16 C17 Br3 -5(2) . . . . ?
C21 C18 N5 C15 178.5(10) . . . . ?
C22 C23 C24 N6 -2.2(19) . . . . ?
C23 C22 C26 C25 0.5(17) . . . . ?
C23 C24 N6 C25 1.6(19) . . . . ?
C26 C22 C23 C24 1.0(17) . . . . ?
C26 C25 N6 C24 0.1(19) . . . . ?
C27 C22 C23 C24 -177.0(11) . . . . ?
C27 C22 C26 C25 178.5(11) . . . . ?
C28 C29 C30 C37 -5.2(19) . . . . ?
C28 C29 C30 N9 178.5(10) . . . . ?
C28 C29 N7 N8 -179.8(9) . . . . ?
C29 C30 C37 C38 -176.6(12) . . . . ?
C29 C30 C37 C42 2(2) . . . . ?
C29 C30 N9 C36 178.0(10) . . . . ?
C29 C30 N9 B2 0.4(17) . . . . ?
C29 N7 N8 C31 -179.9(10) . . . . ?
C29 N7 N8 B2 2.2(15) . . . . ?
C30 C29 N7 N8 0.7(17) . . . . ?
C30 C37 C38 C36 -1.0(13) . . . . ?
C30 C37 C38 Br2 174.4(8) . . . . ?
C31 C32 C35 C34 179.8(11) . . . . ?
C31 C32 C35 C41 0.0(19) . . . . ?
C31 C32 N10 C33 179.3(11) . . . . ?
C32 C31 N8 B2 176.1(11) . . . . ?
C32 C31 N8 N7 -2.0(16) . . . . ?
C33 C34 C35 C32 1.0(13) . . . . ?
C33 C34 C35 C41 -179.3(11) . . . . ?
C34 C33 N10 C32 1.6(13) . . . . ?
C35 C32 N10 C33 -1.0(13) . . . . ?
C37 C30 N9 C36 1.0(13) . . . . ?
C37 C30 N9 B2 -176.7(10) . . . . ?
C38 C36 N9 C30 -1.6(13) . . . . ?
C38 C36 N9 B2 176.1(10) . . . . ?
C39 C36 C38 C37 -179.1(12) . . . . ?
C39 C36 C38 Br2 5.2(19) . . . . ?
C39 C36 N9 C30 179.1(10) . . . . ?
C39 C36 N9 B2 -3.3(18) . . . . ?
C40 C33 C34 C35 -178.0(12) . . . . ?
C40 C33 C34 Br4 2.5(19) . . . . ?
C40 C33 N10 C32 178.5(10) . . . . ?
C42 C37 C38 C36 -179.2(11) . . . . ?
C42 C37 C38 Br2 -3.8(18) . . . . ?
B1 N3 N4 C8 -10.9(15) . . . . ?
Br1 C11 C12 C19 -4.1(19) . . . . ?
Br1 C11 C12 N2 177.8(8) . . . . ?
F1 B1 N2 C9 101.9(15) . . . . ?
F1 B1 N2 C12 -71.4(16) . . . . ?
F1 B1 N3 C14 68.0(13) . . . . ?
F1 B1 N3 N4 -103.3(13) . . . . ?
F2 B1 N2 C9 -124.8(13) . . . . ?
F2 B1 N2 C12 61.8(16) . . . . ?
F2 B1 N3 C14 -54.7(13) . . . . ?
F2 B1 N3 N4 134.0(11) . . . . ?
F4 B2 N8 C31 -56.8(14) . . . . ?
F4 B2 N8 N7 121.1(12) . . . . ?
F4 B2 N9 C30 -119.4(14) . . . . ?
F4 B2 N9 C36 63.4(17) . . . . ?
F5 B2 N8 C31 60.6(13) . . . . ?
F5 B2 N8 N7 -121.5(11) . . . . ?
F5 B2 N9 C30 116.2(13) . . . . ?
F5 B2 N9 C36 -61.0(16) . . . . ?
N1 C4 C5 C1 -0.9(18) . . . . ?
N2 C9 C10 C11 -0.2(13) . . . . ?
N2 C9 C10 C13 177.1(11) . . . . ?
N2 B1 N3 C14 -171.9(9) . . . . ?
N2 B1 N3 N4 16.7(14) . . . . ?
N3 C14 C15 C16 177.7(11) . . . . ?
N3 C14 C15 N5 -2(2) . . . . ?
N3 B1 N2 C9 -13.7(14) . . . . ?
N3 B1 N2 C12 172.9(10) . . . . ?
N4 C8 C9 C10 -175.8(12) . . . . ?
N4 C8 C9 N2 3.6(18) . . . . ?
N5 C15 C16 C17 1.2(13) . . . . ?
N5 C15 C16 C20 178.8(10) . . . . ?
N6 C25 C26 C22 -1(2) . . . . ?
N7 C29 C30 C37 174.3(12) . . . . ?
N7 C29 C30 N9 -2.0(18) . . . . ?
N8 C31 C32 C35 -177.2(11) . . . . ?
N8 C31 C32 N10 2.4(19) . . . . ?
N8 B2 N9 C30 1.8(15) . . . . ?
N8 B2 N9 C36 -175.4(10) . . . . ?
N9 C30 C37 C38 0.0(13) . . . . ?
N9 C30 C37 C42 178.1(11) . . . . ?
N9 C36 C38 C37 1.6(14) . . . . ?
N9 C36 C38 Br2 -174.0(8) . . . . ?
N9 B2 N8 C31 178.8(9) . . . . ?
N9 B2 N8 N7 -3.3(14) . . . . ?
N10 C32 C35 C34 0.1(13) . . . . ?
N10 C32 C35 C41 -179.7(11) . . . . ?
N10 C33 C34 C35 -1.6(14) . . . . ?
N10 C33 C34 Br4 178.8(11) . . . . ?
Br3 C17 C18 C21 8.2(17) . . . . ?
Br3 C17 C18 N5 -174.4(8) . . . . ?
Br4 C34 C35 C32 -179.7(16) . . . . ?
Br4 C34 C35 C41 0(3) . . . . ?
