#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:43:50 +0300 (Tue, 05 May 2020) $
#$Revision: 251562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/62/7126212.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_7126212
loop_
_publ_author_name
'Huang, Jie'
'Li, Feng'
'Cui, Lei'
'Su, Shikuan'
'Jia, Xueshun'
'Li, Jian'
_publ_section_title
;
 Palladium-catalyzed cascade reactions of enynones and isocyanides: access
 towards functionalized ketenimine and its application.
;
_journal_issue                   33
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4555
_journal_page_last               4558
_journal_paper_doi               10.1039/c9cc09363j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C24 H19 Br F3 N O2'
_chemical_formula_weight         490.31
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2400y4
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-11-18 deposited with the CCDC.	2020-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                91.776(2)
_cell_angle_beta                 94.224(2)
_cell_angle_gamma                94.328(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2620(6)
_cell_length_b                   11.3867(8)
_cell_length_c                   22.2514(15)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.35
_cell_measurement_theta_min      3.39
_cell_volume                     2080.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24072
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.999
_diffrn_reflns_theta_min         3.389
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         9035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0905P)²+0.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1576
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7531
_reflns_number_total             9035
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09363j2.cif
_cod_data_source_block           ga_81217e_a
_cod_depositor_comments
'Adding full bibliography for 7126212--7126213.cif.'
_cod_database_code               7126212
_shelx_shelxl_version_number     2014/7
_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_min   0.628
_shelx_estimated_absorpt_t_max   0.709
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
Br1 Br 1.19194(3) 0.82408(2) 1.04346(2) 0.05054(12) Uani 1 1 d . . . . .
F1 F 1.18711(13) 0.84328(10) 0.52698(5) 0.0419(3) Uani 1 1 d . . . . .
F2 F 1.03230(17) 0.72569(10) 0.46634(5) 0.0478(3) Uani 1 1 d . . . . .
F3 F 0.93544(14) 0.87118(10) 0.51090(5) 0.0428(3) Uani 1 1 d . . . . .
N1 N 0.8177(2) 0.63648(14) 0.81205(7) 0.0303(3) Uani 1 1 d . . . . .
O1 O 0.71902(16) 0.34557(11) 0.76364(5) 0.0276(3) Uani 1 1 d . . . . .
O2 O 0.6856(2) -0.01478(13) 0.70846(7) 0.0480(4) Uani 1 1 d . . . . .
C1 C 0.5993(3) 0.16663(19) 0.80285(9) 0.0365(4) Uani 1 1 d . . . . .
H1A H 0.6769 0.1331 0.8317 0.055 Uiso 1 1 calc R U . . .
H1B H 0.5236 0.1034 0.7840 0.055 Uiso 1 1 calc R U . . .
H1C H 0.5383 0.2235 0.8240 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6887(2) 0.22680(16) 0.75587(8) 0.0280(4) Uani 1 1 d . . . . .
C3 C 0.7541(2) 0.18921(16) 0.70461(8) 0.0281(4) Uani 1 1 d . . . . .
C4 C 0.7495(2) 0.06570(16) 0.68196(9) 0.0326(4) Uani 1 1 d . . . . .
C5 C 0.8248(3) 0.04410(18) 0.62341(10) 0.0401(5) Uani 1 1 d . . . . .
H5A H 0.8347 -0.0405 0.6171 0.060 Uiso 1 1 calc R U . . .
H5B H 0.9330 0.0863 0.6249 0.060 Uiso 1 1 calc R U . . .
H5C H 0.7557 0.0725 0.5901 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8313(2) 0.29243(15) 0.67960(8) 0.0280(4) Uani 1 1 d . . . . .
H6 H 0.8884 0.2950 0.6441 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8065(2) 0.38504(16) 0.71664(8) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.8545(2) 0.51072(15) 0.71915(8) 0.0265(3) Uani 1 1 d . . . . .
C9 C 0.8455(2) 0.57229(15) 0.77021(8) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.9155(2) 0.67720(16) 0.86475(8) 0.0278(4) Uani 1 1 d . . . . .
C11 C 0.9204(2) 0.79869(17) 0.87863(8) 0.0318(4) Uani 1 1 d . . . . .
C12 C 1.0054(3) 0.84154(18) 0.93221(9) 0.0363(4) Uani 1 1 d . . . . .
H12 H 1.0114 0.9233 0.9429 0.044 Uiso 1 1 calc R U . . .
C13 C 1.0808(3) 0.76475(19) 0.96959(8) 0.0350(4) Uani 1 1 d . . . . .
C14 C 1.0776(2) 0.64502(19) 0.95554(8) 0.0347(4) Uani 1 1 d . . . . .
H14 H 1.1313 0.5944 0.9822 0.042 Uiso 1 1 calc R U . . .
C15 C 0.9951(2) 0.59967(17) 0.90201(8) 0.0303(4) Uani 1 1 d . . . . .
C16 C 0.8394(3) 0.87978(18) 0.83625(10) 0.0404(5) Uani 1 1 d . . . . .
H16A H 0.8370 0.9574 0.8563 0.061 Uiso 1 1 calc R U . . .
H16B H 0.7278 0.8475 0.8245 0.061 Uiso 1 1 calc R U . . .
H16C H 0.9004 0.8874 0.8002 0.061 Uiso 1 1 calc R U . . .
C17 C 0.9926(3) 0.47042(18) 0.88511(10) 0.0393(5) Uani 1 1 d . . . . .
H17A H 0.8796 0.4372 0.8782 0.059 Uiso 1 1 calc R U . . .
H17B H 1.0478 0.4296 0.9179 0.059 Uiso 1 1 calc R U . . .
H17C H 1.0488 0.4604 0.8482 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9106(2) 0.57532(15) 0.66676(7) 0.0253(3) Uani 1 1 d . . . . .
C19 C 1.0017(2) 0.68372(16) 0.67652(8) 0.0291(4) Uani 1 1 d . . . . .
H19 H 1.0349 0.7110 0.7166 0.035 Uiso 1 1 calc R U . . .
C20 C 1.0443(2) 0.75198(16) 0.62898(8) 0.0306(4) Uani 1 1 d . . . . .
H20 H 1.1035 0.8265 0.6363 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9994(2) 0.71008(15) 0.57020(8) 0.0270(4) Uani 1 1 d . . . . .
C22 C 0.9142(2) 0.60121(15) 0.55969(8) 0.0276(4) Uani 1 1 d . . . . .
H22 H 0.8863 0.5722 0.5195 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8694(2) 0.53451(15) 0.60743(8) 0.0277(4) Uani 1 1 d . . . . .
H23 H 0.8100 0.4602 0.5998 0.033 Uiso 1 1 calc R U . . .
C24 C 1.0387(2) 0.78645(16) 0.51911(8) 0.0307(4) Uani 1 1 d . . . . .
Br2 Br 0.68946(3) 0.82244(2) 1.04293(2) 0.04984(12) Uani 1 1 d . . . . .
F4 F 0.65993(13) 0.71689(10) 0.47927(5) 0.0405(3) Uani 1 1 d . . . . .
F5 F 0.54895(17) 0.87006(9) 0.50985(5) 0.0475(3) Uani 1 1 d . . . . .
F6 F 0.40824(14) 0.73388(10) 0.45573(4) 0.0423(3) Uani 1 1 d . . . . .
N2 N 0.3196(2) 0.64230(14) 0.80943(7) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.21787(16) 0.35353(11) 0.76302(5) 0.0278(3) Uani 1 1 d . . . . .
O4 O 0.1878(2) -0.00827(13) 0.71122(7) 0.0474(4) Uani 1 1 d . . . . .
C25 C 0.0996(3) 0.17580(18) 0.80397(9) 0.0356(4) Uani 1 1 d . . . . .
H25A H 0.1772 0.1433 0.8332 0.053 Uiso 1 1 calc R U . . .
H25B H 0.0243 0.1119 0.7855 0.053 Uiso 1 1 calc R U . . .
H25C H 0.0381 0.2332 0.8245 0.053 Uiso 1 1 calc R U . . .
C26 C 0.1889(2) 0.23458(16) 0.75661(8) 0.0285(4) Uani 1 1 d . . . . .
C27 C 0.2560(2) 0.19528(16) 0.70593(8) 0.0287(4) Uani 1 1 d . . . . .
C28 C 0.2536(3) 0.07135(17) 0.68450(9) 0.0333(4) Uani 1 1 d . . . . .
C29 C 0.3321(3) 0.04832(18) 0.62691(10) 0.0404(5) Uani 1 1 d . . . . .
H29A H 0.3485 -0.0358 0.6226 0.061 Uiso 1 1 calc R U . . .
H29B H 0.4374 0.0943 0.6280 0.061 Uiso 1 1 calc R U . . .
H29C H 0.2615 0.0714 0.5927 0.061 Uiso 1 1 calc R U . . .
C30 C 0.3321(2) 0.29740(16) 0.67988(8) 0.0291(4) Uani 1 1 d . . . . .
H30 H 0.3898 0.2988 0.6445 0.035 Uiso 1 1 calc R U . . .
C31 C 0.3054(2) 0.39104(15) 0.71575(8) 0.0268(4) Uani 1 1 d . . . . .
C32 C 0.3523(2) 0.51699(15) 0.71588(8) 0.0268(4) Uani 1 1 d . . . . .
C33 C 0.3477(2) 0.58088(15) 0.76660(8) 0.0282(4) Uani 1 1 d . . . . .
C34 C 0.4156(2) 0.68119(16) 0.86266(8) 0.0276(4) Uani 1 1 d . . . . .
C35 C 0.4202(2) 0.80211(17) 0.87770(8) 0.0315(4) Uani 1 1 d . . . . .
C36 C 0.5041(3) 0.84329(18) 0.93165(9) 0.0360(4) Uani 1 1 d . . . . .
H36 H 0.5100 0.9248 0.9429 0.043 Uiso 1 1 calc R U . . .
C37 C 0.5785(3) 0.76531(19) 0.96874(8) 0.0350(4) Uani 1 1 d . . . . .
C38 C 0.5742(2) 0.64584(19) 0.95369(8) 0.0339(4) Uani 1 1 d . . . . .
H38 H 0.6263 0.5941 0.9802 0.041 Uiso 1 1 calc R U . . .
C39 C 0.4933(2) 0.60234(17) 0.89969(8) 0.0295(4) Uani 1 1 d . . . . .
C40 C 0.3394(3) 0.88424(18) 0.83580(10) 0.0397(5) Uani 1 1 d . . . . .
H40A H 0.3415 0.9625 0.8556 0.060 Uiso 1 1 calc R U . . .
H40B H 0.2263 0.8541 0.8253 0.060 Uiso 1 1 calc R U . . .
H40C H 0.3976 0.8899 0.7990 0.060 Uiso 1 1 calc R U . . .
C41 C 0.4893(3) 0.47303(18) 0.88202(10) 0.0382(4) Uani 1 1 d . . . . .
H41A H 0.3761 0.4408 0.8743 0.057 Uiso 1 1 calc R U . . .
H41B H 0.5423 0.4310 0.9148 0.057 Uiso 1 1 calc R U . . .
H41C H 0.5470 0.4633 0.8455 0.057 Uiso 1 1 calc R U . . .
C42 C 0.4017(2) 0.57542(15) 0.66072(8) 0.0264(4) Uani 1 1 d . . . . .
C43 C 0.5012(2) 0.68038(16) 0.66518(8) 0.0302(4) Uani 1 1 d . . . . .
H43 H 0.5427 0.7118 0.7038 0.036 Uiso 1 1 calc R U . . .
C44 C 0.5404(2) 0.73969(16) 0.61386(8) 0.0324(4) Uani 1 1 d . . . . .
H44 H 0.6065 0.8119 0.6174 0.039 Uiso 1 1 calc R U . . .
C45 C 0.4822(2) 0.69261(15) 0.55735(8) 0.0269(4) Uani 1 1 d . . . . .
C46 C 0.3857(2) 0.58732(16) 0.55234(8) 0.0298(4) Uani 1 1 d . . . . .
H46 H 0.3474 0.5546 0.5137 0.036 Uiso 1 1 calc R U . . .
C47 C 0.3454(2) 0.52999(16) 0.60357(8) 0.0299(4) Uani 1 1 d . . . . .
H47 H 0.2780 0.4583 0.5997 0.036 Uiso 1 1 calc R U . . .
C48 C 0.5241(2) 0.75357(16) 0.50144(8) 0.0317(4) 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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 '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
C9 N1 C10 131.20(17) . . ?
C2 O1 C7 107.90(13) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.56(15) . . ?
O1 C2 C1 116.34(16) . . ?
C3 C2 C1 134.08(18) . . ?
C2 C3 C6 106.46(16) . . ?
C2 C3 C4 125.50(17) . . ?
C6 C3 C4 128.00(17) . . ?
O2 C4 C3 121.89(19) . . ?
O2 C4 C5 121.27(18) . . ?
C3 C4 C5 116.83(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 106.63(16) . . ?
C7 C6 H6 126.7 . . ?
C3 C6 H6 126.7 . . ?
C6 C7 O1 109.44(15) . . ?
C6 C7 C8 135.40(17) . . ?
O1 C7 C8 115.12(15) . . ?
C9 C8 C7 119.18(16) . . ?
C9 C8 C18 117.55(16) . . ?
C7 C8 C18 123.26(15) . . ?
N1 C9 C8 169.8(2) . . ?
C15 C10 C11 122.28(18) . . ?
C15 C10 N1 121.62(16) . . ?
C11 C10 N1 116.02(16) . . ?
C12 C11 C10 118.09(18) . . ?
C12 C11 C16 121.18(18) . . ?
C10 C11 C16 120.72(18) . . ?
C13 C12 C11 119.62(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 122.30(18) . . ?
C12 C13 Br1 119.08(16) . . ?
C14 C13 Br1 118.61(16) . . ?
C13 C14 C15 119.46(18) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 118.22(18) . . ?
C14 C15 C17 120.51(18) . . ?
C10 C15 C17 121.27(18) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.34(15) . . ?
C23 C18 C8 122.25(16) . . ?
C19 C18 C8 119.35(15) . . ?
C20 C19 C18 121.36(16) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.13(17) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.25(16) . . ?
C22 C21 C24 120.74(16) . . ?
C20 C21 C24 118.96(16) . . ?
C23 C22 C21 120.26(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.61(17) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
F1 C24 F2 106.79(14) . . ?
F1 C24 F3 105.32(14) . . ?
F2 C24 F3 105.85(15) . . ?
F1 C24 C21 113.03(15) . . ?
F2 C24 C21 112.56(15) . . ?
F3 C24 C21 112.69(14) . . ?
C33 N2 C34 131.94(17) . . ?
C26 O3 C31 107.80(13) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 C27 109.44(15) . . ?
O3 C26 C25 116.53(16) . . ?
C27 C26 C25 134.01(18) . . ?
C26 C27 C30 106.60(16) . . ?
C26 C27 C28 125.72(17) . . ?
C30 C27 C28 127.65(17) . . ?
O4 C28 C27 121.70(19) . . ?
O4 C28 C29 121.48(18) . . ?
C27 C28 C29 116.79(17) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C27 106.46(16) . . ?
C31 C30 H30 126.8 . . ?
C27 C30 H30 126.8 . . ?
C30 C31 O3 109.71(15) . . ?
C30 C31 C32 134.44(17) . . ?
O3 C31 C32 115.81(15) . . ?
C33 C32 C31 118.80(16) . . ?
C33 C32 C42 119.52(16) . . ?
C31 C32 C42 121.67(15) . . ?
N2 C33 C32 170.0(2) . . ?
C39 C34 C35 122.17(17) . . ?
C39 C34 N2 121.63(16) . . ?
C35 C34 N2 116.10(16) . . ?
C36 C35 C34 118.23(17) . . ?
C36 C35 C40 121.31(18) . . ?
C34 C35 C40 120.45(18) . . ?
C37 C36 C35 119.69(18) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 121.97(18) . . ?
C36 C37 Br2 119.21(16) . . ?
C38 C37 Br2 118.82(16) . . ?
C37 C38 C39 119.66(18) . . ?
C37 C38 H38 120.2 . . ?
C39 C38 H38 120.2 . . ?
C38 C39 C34 118.26(17) . . ?
C38 C39 C41 120.51(17) . . ?
C34 C39 C41 121.23(17) . . ?
C35 C40 H40A 109.5 . . ?
C35 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C35 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C47 C42 C43 118.42(16) . . ?
C47 C42 C32 121.19(16) . . ?
C43 C42 C32 120.34(16) . . ?
C44 C43 C42 120.88(17) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C45 C44 C43 119.54(17) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C46 C45 C44 120.06(16) . . ?
C46 C45 C48 119.23(16) . . ?
C44 C45 C48 120.71(16) . . ?
C47 C46 C45 120.00(17) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C42 121.08(17) . . ?
C46 C47 H47 119.5 . . ?
C42 C47 H47 119.5 . . ?
F5 C48 F6 106.65(14) . . ?
F5 C48 F4 106.38(15) . . ?
F6 C48 F4 104.60(15) . . ?
F5 C48 C45 112.93(15) . . ?
F6 C48 C45 113.03(15) . . ?
F4 C48 C45 112.62(14) . . ?
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 C13 1.902(2) . ?
F1 C24 1.339(2) . ?
F2 C24 1.340(2) . ?
F3 C24 1.343(2) . ?
N1 C9 1.212(2) . ?
N1 C10 1.419(2) . ?
O1 C2 1.360(2) . ?
O1 C7 1.382(2) . ?
O2 C4 1.214(3) . ?
C1 C2 1.479(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.368(3) . ?
C3 C6 1.441(2) . ?
C3 C4 1.476(3) . ?
C4 C5 1.506(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.355(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.454(2) . ?
C8 C9 1.326(3) . ?
C8 C18 1.482(2) . ?
C10 C15 1.398(3) . ?
C10 C11 1.405(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.498(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C17 1.506(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.395(2) . ?
C18 C19 1.398(3) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(2) . ?
C21 C24 1.492(2) . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
Br2 C37 1.900(2) . ?
F4 C48 1.348(2) . ?
F5 C48 1.332(2) . ?
F6 C48 1.345(2) . ?
N2 C33 1.211(2) . ?
N2 C34 1.416(2) . ?
O3 C26 1.359(2) . ?
O3 C31 1.380(2) . ?
O4 C28 1.216(3) . ?
C25 C26 1.479(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.370(3) . ?
C27 C30 1.438(2) . ?
C27 C28 1.474(3) . ?
C28 C29 1.503(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.353(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.457(2) . ?
C32 C33 1.328(3) . ?
C32 C42 1.483(2) . ?
C34 C39 1.397(3) . ?
C34 C35 1.404(3) . ?
C35 C36 1.391(3) . ?
C35 C40 1.499(3) . ?
C36 C37 1.379(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.388(3) . ?
C38 C39 1.389(3) . ?
C38 H38 0.9500 . ?
C39 C41 1.510(3) . ?
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 C47 1.392(3) . ?
C42 C43 1.395(3) . ?
C43 C44 1.391(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.389(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.385(2) . ?
C45 C48 1.493(2) . ?
C46 C47 1.381(2) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
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
C7 O1 C2 C3 -0.35(19) . . . . ?
C7 O1 C2 C1 178.35(16) . . . . ?
O1 C2 C3 C6 0.5(2) . . . . ?
C1 C2 C3 C6 -177.8(2) . . . . ?
O1 C2 C3 C4 178.51(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 O2 -0.5(3) . . . . ?
C6 C3 C4 O2 177.0(2) . . . . ?
C2 C3 C4 C5 178.17(19) . . . . ?
C6 C3 C4 C5 -4.3(3) . . . . ?
C2 C3 C6 C7 -0.5(2) . . . . ?
C4 C3 C6 C7 -178.43(18) . . . . ?
C3 C6 C7 O1 0.3(2) . . . . ?
C3 C6 C7 C8 177.7(2) . . . . ?
C2 O1 C7 C6 0.00(19) . . . . ?
C2 O1 C7 C8 -177.95(15) . . . . ?
C6 C7 C8 C9 -162.4(2) . . . . ?
O1 C7 C8 C9 14.8(2) . . . . ?
C6 C7 C8 C18 18.8(3) . . . . ?
O1 C7 C8 C18 -163.96(16) . . . . ?
C10 N1 C9 C8 -159.5(10) . . . . ?
C7 C8 C9 N1 -110.5(11) . . . . ?
C18 C8 C9 N1 68.4(11) . . . . ?
C9 N1 C10 C15 -50.8(3) . . . . ?
C9 N1 C10 C11 132.3(2) . . . . ?
C15 C10 C11 C12 -1.3(3) . . . . ?
N1 C10 C11 C12 175.54(16) . . . . ?
C15 C10 C11 C16 177.36(18) . . . . ?
N1 C10 C11 C16 -5.8(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C16 C11 C12 C13 -178.86(19) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 Br1 -178.50(15) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
Br1 C13 C14 C15 179.20(14) . . . . ?
C13 C14 C15 C10 -1.2(3) . . . . ?
C13 C14 C15 C17 178.79(18) . . . . ?
C11 C10 C15 C14 2.0(3) . . . . ?
N1 C10 C15 C14 -174.69(16) . . . . ?
C11 C10 C15 C17 -177.95(17) . . . . ?
N1 C10 C15 C17 5.3(3) . . . . ?
C9 C8 C18 C23 -155.47(18) . . . . ?
C7 C8 C18 C23 23.3(3) . . . . ?
C9 C8 C18 C19 21.4(3) . . . . ?
C7 C8 C18 C19 -159.75(17) . . . . ?
C23 C18 C19 C20 2.8(3) . . . . ?
C8 C18 C19 C20 -174.21(17) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C19 C20 C21 C24 177.11(17) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C24 C21 C22 C23 -175.87(16) . . . . ?
C21 C22 C23 C18 -0.6(3) . . . . ?
C19 C18 C23 C22 -1.6(3) . . . . ?
C8 C18 C23 C22 175.34(17) . . . . ?
C22 C21 C24 F1 -141.42(16) . . . . ?
C20 C21 C24 F1 41.1(2) . . . . ?
C22 C21 C24 F2 -20.3(2) . . . . ?
C20 C21 C24 F2 162.17(16) . . . . ?
C22 C21 C24 F3 99.30(19) . . . . ?
C20 C21 C24 F3 -78.2(2) . . . . ?
C31 O3 C26 C27 -0.18(19) . . . . ?
C31 O3 C26 C25 178.39(16) . . . . ?
O3 C26 C27 C30 0.4(2) . . . . ?
C25 C26 C27 C30 -177.8(2) . . . . ?
O3 C26 C27 C28 178.51(17) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
C26 C27 C28 O4 0.7(3) . . . . ?
C30 C27 C28 O4 178.4(2) . . . . ?
C26 C27 C28 C29 178.83(19) . . . . ?
C30 C27 C28 C29 -3.5(3) . . . . ?
C26 C27 C30 C31 -0.5(2) . . . . ?
C28 C27 C30 C31 -178.54(18) . . . . ?
C27 C30 C31 O3 0.4(2) . . . . ?
C27 C30 C31 C32 178.1(2) . . . . ?
C26 O3 C31 C30 -0.1(2) . . . . ?
C26 O3 C31 C32 -178.32(15) . . . . ?
C30 C31 C32 C33 -160.4(2) . . . . ?
O3 C31 C32 C33 17.2(3) . . . . ?
C30 C31 C32 C42 20.8(3) . . . . ?
O3 C31 C32 C42 -161.57(16) . . . . ?
C34 N2 C33 C32 -178.5(10) . . . . ?
C31 C32 C33 N2 -92.9(11) . . . . ?
C42 C32 C33 N2 85.9(11) . . . . ?
C33 N2 C34 C39 -52.2(3) . . . . ?
C33 N2 C34 C35 131.4(2) . . . . ?
C39 C34 C35 C36 -0.6(3) . . . . ?
N2 C34 C35 C36 175.84(16) . . . . ?
C39 C34 C35 C40 178.16(18) . . . . ?
N2 C34 C35 C40 -5.4(3) . . . . ?
C34 C35 C36 C37 -0.5(3) . . . . ?
C40 C35 C36 C37 -179.23(19) . . . . ?
C35 C36 C37 C38 0.7(3) . . . . ?
C35 C36 C37 Br2 -178.93(15) . . . . ?
C36 C37 C38 C39 0.2(3) . . . . ?
Br2 C37 C38 C39 179.84(14) . . . . ?
C37 C38 C39 C34 -1.2(3) . . . . ?
C37 C38 C39 C41 179.05(18) . . . . ?
C35 C34 C39 C38 1.4(3) . . . . ?
N2 C34 C39 C38 -174.75(16) . . . . ?
C35 C34 C39 C41 -178.85(17) . . . . ?
N2 C34 C39 C41 4.9(3) . . . . ?
C33 C32 C42 C47 -152.09(19) . . . . ?
C31 C32 C42 C47 26.7(3) . . . . ?
C33 C32 C42 C43 25.3(3) . . . . ?
C31 C32 C42 C43 -155.87(18) . . . . ?
C47 C42 C43 C44 1.4(3) . . . . ?
C32 C42 C43 C44 -176.14(17) . . . . ?
C42 C43 C44 C45 -1.2(3) . . . . ?
C43 C44 C45 C46 0.0(3) . . . . ?
C43 C44 C45 C48 -179.22(17) . . . . ?
C44 C45 C46 C47 1.0(3) . . . . ?
C48 C45 C46 C47 -179.77(17) . . . . ?
C45 C46 C47 C42 -0.8(3) . . . . ?
C43 C42 C47 C46 -0.3(3) . . . . ?
C32 C42 C47 C46 177.13(17) . . . . ?
C46 C45 C48 F5 151.33(16) . . . . ?
C44 C45 C48 F5 -29.4(2) . . . . ?
C46 C45 C48 F6 30.1(2) . . . . ?
C44 C45 C48 F6 -150.60(16) . . . . ?
C46 C45 C48 F4 -88.1(2) . . . . ?
C44 C45 C48 F4 91.1(2) . . . . ?
