#------------------------------------------------------------------------------
#$Date: 2022-04-13 01:13:22 +0300 (Wed, 13 Apr 2022) $
#$Revision: 274496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566784.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_1566784
loop_
_publ_author_name
'Liu, Hong-Chao'
'Kong, Xiangtao'
'Gong, Xiao-Ping'
'Li, Yuke'
'Niu, Zhi-Jie'
'Gou, Xue-Ya'
'Li, Xue-Song'
'Wang, Yu-Zhao'
'Shi, Wei-Yu'
'Huang, Yan-Chong'
'Liu, Xue-Yuan'
'Liang, Yong-Min'
_publ_section_title
;
 Site-Selective Coupling of Remote C(sp3)−H/meta-C(sp2)−H
 Bonds Enabled by Ru/Photoredox Dual Catalysis and Mechanistic Studies
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00764A
_journal_year                    2022
_chemical_formula_moiety         'C20 H26 Br N3 O'
_chemical_formula_sum            'C20 H26 Br N3 O'
_chemical_formula_weight         404.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-08-26 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3165(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.36816(5)
_cell_length_b                   31.0073(3)
_cell_length_c                   10.01092(9)
_cell_measurement_reflns_used    10668
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.1290
_cell_measurement_theta_min      4.6600
_cell_volume                     1960.66(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  79.00   0.50    0.05    --   46.32  61.00 -91.00   50
  2  ω    104.00 164.00   0.50    0.05    --  104.25  61.00-180.00  120
  3  ω     88.00 174.00   0.50    0.05    --  104.25  61.00 -91.00  172
  4  ω     97.00 152.00   0.50    0.05    --  104.25  45.00 -30.00  110
  5  ω     32.00 102.00   0.50    0.05    --  104.25 -77.00 -90.00  140
  6  ω     32.00  59.00   0.50    0.05    --  104.25 -61.00-150.00   54
  7  ω     40.00  73.00   0.50    0.05    --  104.25 -61.00 -30.00   66
  8  ω     32.00  57.00   0.50    0.05    --  104.25 -61.00 129.00   50
  9  ω    -25.00  48.00   0.50    0.05    --   46.32 -61.00 129.00  146
 10  ω    -63.00  25.00   0.50    0.05    --  -46.32  61.00 -91.00  176
 11  ω    -68.00 -32.00   0.50    0.05    -- -102.00  61.00-120.00   72
 12  ω    -63.00 -38.00   0.50    0.05    -- -102.00  61.00 -91.00   50
 13  ω    -68.00 -38.00   0.50    0.05    -- -102.00  61.00  30.00   60
 14  ω    -91.00 -30.00   0.50    0.05    -- -102.00 125.00 120.00  122
 15  ω     33.00 111.00   0.50    0.05    --  104.25-125.00 120.00  156
 16  ω   -154.00-129.00   0.50    0.05    -- -102.00 -61.00 129.00   50
 17  ω   -175.00-137.00   0.50    0.05    -- -102.00 -94.00  60.00   76
 18  ω   -129.00 -87.00   0.50    0.05    -- -102.00 -94.00  60.00   84
 19  ω   -106.00 -56.00   0.50    0.05    --  -46.32 -61.00 129.00  100
 20  ω    -84.00 -74.00   0.50    0.05    --  -46.32-125.00 -90.00   20
;
_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      -0.1724598000
_diffrn_orient_matrix_UB_12      -0.0338315000
_diffrn_orient_matrix_UB_13      0.0154983000
_diffrn_orient_matrix_UB_21      -0.0105282000
_diffrn_orient_matrix_UB_22      -0.0113671000
_diffrn_orient_matrix_UB_23      -0.1505002000
_diffrn_orient_matrix_UB_31      0.1721716000
_diffrn_orient_matrix_UB_32      -0.0345656000
_diffrn_orient_matrix_UB_33      0.0343199000
_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  0.0243
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12690
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.447
_diffrn_reflns_theta_min         4.676
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00261(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0272
_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)+(0.0261P)²+1.1912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00764a2.cif
_cod_data_source_block           liuhch_0824_auto
_cod_original_cell_volume        1960.65(3)
_cod_database_code               1566784
_shelx_shelxl_version_number     2018/1
_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.
;
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), 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 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.567
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 -0.25472(3) 0.48498(2) 0.10377(2) 0.03008(9) Uani 1 1 d . . . . .
O1 O 0.5999(2) 0.25367(4) 1.08107(12) 0.0317(3) Uani 1 1 d . . . . .
N1 N 0.2497(2) 0.45675(5) 0.38902(13) 0.0215(3) Uani 1 1 d . . . . .
N2 N -0.0646(2) 0.44127(4) 0.48706(14) 0.0223(3) Uani 1 1 d . . . . .
N3 N 0.6582(2) 0.23015(5) 0.87544(14) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.633630 0.235069 0.788280 0.033 Uiso 1 1 calc R U . . .
C1 C 0.1468(2) 0.44297(5) 0.49036(16) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.1308(3) 0.46936(5) 0.27669(17) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.197938 0.479518 0.203258 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0875(3) 0.46807(5) 0.26423(16) 0.0208(3) Uani 1 1 d . . . . .
C4 C -0.1810(3) 0.45370(6) 0.37338(16) 0.0232(3) Uani 1 1 d . . . . .
H4 H -0.331007 0.452668 0.367253 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2767(2) 0.42870(5) 0.61619(15) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.4857(2) 0.44237(5) 0.64543(17) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.547061 0.460504 0.584433 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6032(2) 0.42923(5) 0.76454(17) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.745894 0.438444 0.785268 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5142(3) 0.40278(5) 0.85353(17) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.596613 0.394511 0.935344 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3059(2) 0.38794(5) 0.82585(16) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.1888(2) 0.40162(5) 0.70638(16) 0.0185(3) Uani 1 1 d . . . . .
H10 H 0.046189 0.392376 0.685571 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2108(3) 0.36013(5) 0.92990(17) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.0011(3) 0.33896(6) 0.8724(2) 0.0292(4) Uani 1 1 d . . . . .
H12A H -0.103641 0.361385 0.844053 0.044 Uiso 1 1 calc R U . . .
H12B H -0.050488 0.320906 0.941689 0.044 Uiso 1 1 calc R U . . .
H12C H 0.023280 0.321074 0.794732 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1699(3) 0.39023(6) 1.04608(19) 0.0331(4) Uani 1 1 d . . . . .
H13A H 0.303481 0.403490 1.085049 0.050 Uiso 1 1 calc R U . . .
H13B H 0.110479 0.373540 1.115465 0.050 Uiso 1 1 calc R U . . .
H13C H 0.069688 0.412814 1.011689 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3660(3) 0.32469(5) 0.98876(16) 0.0220(3) Uani 1 1 d . . . . .
H14A H 0.494372 0.338822 1.035339 0.026 Uiso 1 1 calc R U . . .
H14B H 0.299189 0.308506 1.057416 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4341(3) 0.29263(5) 0.88765(16) 0.0224(3) Uani 1 1 d . . . . .
H15A H 0.513706 0.307961 0.823388 0.027 Uiso 1 1 calc R U . . .
H15B H 0.306913 0.279598 0.835944 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5725(3) 0.25707(5) 0.95762(16) 0.0215(3) Uani 1 1 d . . . . .
C17 C 0.7918(3) 0.19258(6) 0.92137(18) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.8507(5) 0.17049(9) 0.7953(2) 0.0647(9) Uani 1 1 d . . . . .
H18A H 0.722552 0.159113 0.742409 0.097 Uiso 1 1 calc R U . . .
H18B H 0.949024 0.146746 0.821335 0.097 Uiso 1 1 calc R U . . .
H18C H 0.918342 0.191395 0.741034 0.097 Uiso 1 1 calc R U . . .
C19 C 0.9936(3) 0.20807(7) 1.0075(3) 0.0454(5) Uani 1 1 d . . . . .
H19A H 1.071334 0.227552 0.954374 0.068 Uiso 1 1 calc R U . . .
H19B H 1.082678 0.183191 1.036686 0.068 Uiso 1 1 calc R U . . .
H19C H 0.955808 0.223401 1.086706 0.068 Uiso 1 1 calc R U . . .
C20 C 0.6681(3) 0.16146(6) 0.9993(2) 0.0368(4) Uani 1 1 d . . . . .
H20A H 0.632192 0.175650 1.080855 0.055 Uiso 1 1 calc R U . . .
H20B H 0.754563 0.135877 1.024305 0.055 Uiso 1 1 calc R U . . .
H20C H 0.537767 0.152824 0.942795 0.055 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'
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
C2 N1 C1 116.78(14) . . ?
C4 N2 C1 117.12(14) . . ?
C16 N3 H3 117.8 . . ?
C16 N3 C17 124.32(14) . . ?
C17 N3 H3 117.8 . . ?
N1 C1 C5 117.55(13) . . ?
N2 C1 N1 125.22(14) . . ?
N2 C1 C5 117.23(13) . . ?
N1 C2 H2 119.1 . . ?
N1 C2 C3 121.71(15) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 Br1 121.47(12) . . ?
C2 C3 C4 117.90(15) . . ?
C4 C3 Br1 120.63(12) . . ?
N2 C4 C3 121.26(15) . . ?
N2 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C1 120.15(14) . . ?
C6 C5 C10 119.78(14) . . ?
C10 C5 C1 120.07(14) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.24(15) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.50(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.56(15) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C11 119.77(14) . . ?
C10 C9 C8 117.42(14) . . ?
C10 C9 C11 122.69(14) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.49(14) . . ?
C9 C10 H10 119.3 . . ?
C9 C11 C13 106.95(13) . . ?
C9 C11 C14 111.74(13) . . ?
C12 C11 C9 112.68(14) . . ?
C12 C11 C13 108.66(15) . . ?
C12 C11 C14 108.88(14) . . ?
C13 C11 C14 107.76(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C11 115.73(13) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.34(13) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
O1 C16 N3 123.23(15) . . ?
O1 C16 C15 121.53(14) . . ?
N3 C16 C15 115.24(14) . . ?
N3 C17 C18 106.78(15) . . ?
N3 C17 C19 109.63(16) . . ?
N3 C17 C20 110.07(15) . . ?
C18 C17 C19 109.3(2) . . ?
C20 C17 C18 109.7(2) . . ?
C20 C17 C19 111.25(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 . . ?
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 C3 1.8851(16) . ?
O1 C16 1.230(2) . ?
N1 C1 1.345(2) . ?
N1 C2 1.332(2) . ?
N2 C1 1.344(2) . ?
N2 C4 1.333(2) . ?
N3 H3 0.8800 . ?
N3 C16 1.336(2) . ?
N3 C17 1.481(2) . ?
C1 C5 1.484(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 C10 1.401(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(2) . ?
C9 C10 1.392(2) . ?
C9 C11 1.535(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.533(2) . ?
C11 C13 1.539(2) . ?
C11 C14 1.544(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.521(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(2) . ?
C17 C18 1.524(3) . ?
C17 C19 1.531(3) . ?
C17 C20 1.522(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 C3 C4 N2 179.39(12) . . . . ?
N1 C1 C5 C6 21.2(2) . . . . ?
N1 C1 C5 C10 -159.23(14) . . . . ?
N1 C2 C3 Br1 -178.82(12) . . . . ?
N1 C2 C3 C4 0.9(2) . . . . ?
N2 C1 C5 C6 -158.54(15) . . . . ?
N2 C1 C5 C10 21.1(2) . . . . ?
C1 N1 C2 C3 -0.5(2) . . . . ?
C1 N2 C4 C3 -0.6(2) . . . . ?
C1 C5 C6 C7 178.96(14) . . . . ?
C1 C5 C10 C9 -179.45(14) . . . . ?
C2 N1 C1 N2 -0.4(2) . . . . ?
C2 N1 C1 C5 179.87(14) . . . . ?
C2 C3 C4 N2 -0.3(2) . . . . ?
C4 N2 C1 N1 1.0(2) . . . . ?
C4 N2 C1 C5 -179.33(14) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C10 -1.5(2) . . . . ?
C7 C8 C9 C11 -177.60(15) . . . . ?
C8 C9 C10 C5 0.9(2) . . . . ?
C8 C9 C11 C12 -167.92(14) . . . . ?
C8 C9 C11 C13 72.74(18) . . . . ?
C8 C9 C11 C14 -45.0(2) . . . . ?
C9 C11 C14 C15 -60.22(19) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C10 C9 C11 C12 16.2(2) . . . . ?
C10 C9 C11 C13 -103.16(18) . . . . ?
C10 C9 C11 C14 139.14(15) . . . . ?
C11 C9 C10 C5 176.89(14) . . . . ?
C11 C14 C15 C16 -175.41(14) . . . . ?
C12 C11 C14 C15 64.89(18) . . . . ?
C13 C11 C14 C15 -177.43(15) . . . . ?
C14 C15 C16 O1 7.6(2) . . . . ?
C14 C15 C16 N3 -173.04(15) . . . . ?
C16 N3 C17 C18 178.7(2) . . . . ?
C16 N3 C17 C19 -63.0(2) . . . . ?
C16 N3 C17 C20 59.7(2) . . . . ?
C17 N3 C16 O1 1.4(3) . . . . ?
C17 N3 C16 C15 -177.92(16) . . . . ?
