#------------------------------------------------------------------------------
#$Date: 2019-01-11 01:46:54 +0200 (Fri, 11 Jan 2019) $
#$Revision: 212912 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/04/1550415.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_1550415
loop_
_publ_author_name
'Sindt, Ammon J.'
'DeHaven, Baillie A.'
'McEachern, David F.'
'Dissanayake, Madushanka M.'
'Smith, Mark D.'
'Vannucci, Aaron K.'
'Shimizu, Linda S.'
_publ_section_title
;
 UV-irradiation of self-assembled triphenylamines affords persistent and
 regenerable radicals
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC04607G
_journal_year                    2019
_chemical_formula_moiety         'C39 H32 Br2 N4 O'
_chemical_formula_sum            'C39 H32 Br2 N4 O'
_chemical_formula_weight         732.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-12 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5184(8)
_cell_length_b                   19.9443(7)
_cell_length_c                   9.0043(4)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.71
_cell_volume                     3325.6(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            123401
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        27.184
_diffrn_reflns_theta_max         27.184
_diffrn_reflns_theta_min         2.200
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.475
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0542 before and 0.0430 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0440
_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)+(0.0697P)²+5.2665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3057
_reflns_number_total             3695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8sc04607g2.cif
_cod_data_source_block           brnph3su_dp
_cod_database_code               1550415
_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.
;
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.664
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{O1A, O1B}
{C1A, C1B}
3. Restrained distances
 N1B-H1A = N1A-H1A
 0.84 with sigma of 0.02
 C11B-Br1B \\sim C13B-Br1B
 with sigma of 0.005
4. Restrained planarity
 N2B, C9B, C10B, C11B, C12B, Br1B, C13B, C14B
 with sigma of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1B)
Uanis(C1A) = Uanis(C1B)
Uanis(N1B) = Uanis(N1A)
Uanis(C2B) = Uanis(C2A)
Uanis(C3B) = Uanis(C3A)
Uanis(C6B) = Uanis(C7A)
Uanis(C7B) = Uanis(C6A)
Uanis(C4A) = Uanis(C8B)
Uanis(C8A) = Uanis(C5B)
Uanis(C20A) = Uanis(C16B)
Uanis(C17B) = Uanis(C19A)
Uanis(C18B) = Uanis(C18A)
Uanis(C19B) = Uanis(C17A)
Uanis(C16A) = Uanis(C20B)
Uanis(C8A) = Uanis(C4B)
Uanis(C13B) = Uanis(C14A)
Uanis(C13A) = Uanis(C12B)
Uanis(C11B) = Uanis(C12A)
Uanis(C10B) = Uanis(C11A)
Uanis(C9B) = Uanis(C10A)
Uanis(C9A) = Uanis(C14B)
Uanis(N2A) = Uanis(N2B)
6. Same fragment restrains
{Br1A, O1A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A,
C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, C20A} sigma for 1-2: 0.015,
1-3: 0.04
as
{Br1B, O1B, N1B, N2B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B,
C12B, C13B, C14B, C15B, C16B, C17B, C18B, C19B, C20B}
7. Others
 Sof(Br1B)=Sof(N1B)=Sof(N2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=
 Sof(C9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(H13B)=
 Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=1-FVAR(1)
 Sof(O1B)=Sof(C1B)=0.5*(1-FVAR(2))
 Sof(O1A)=Sof(C1A)=0.5*FVAR(2)
 Sof(Br1A)=Sof(N1A)=Sof(N2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(C4A)=
 Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=FVAR(1)
8.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB)
8.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A),
 C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B), C10B(H10B), C11B(H11B), C13B(H13B),
 C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
Br1A Br 0.64962(2) 0.69893(2) -0.02322(4) 0.03874(15) Uani 0.9095(12) 1 d D . .
A 1
O1A O 0.250000 0.750000 1.0881(3) 0.0331(6) Uani 0.9095(12) 2 d DS T P A 1
N1A N 0.30633(12) 0.72469(13) 0.8740(3) 0.0198(5) Uani 0.9095(12) 1 d D . . A 1
N2A N 0.57531(13) 0.57251(13) 0.5733(3) 0.0274(5) Uani 0.9095(12) 1 d D . . A 1
C1A C 0.250000 0.750000 0.9506(4) 0.0225(7) Uani 0.9095(12) 2 d DS T P A 1
C2A C 0.37105(18) 0.70353(19) 0.9526(4) 0.0343(8) Uani 0.9095(12) 1 d D . . A 1
H2AA H 0.357385 0.673081 1.034767 0.041 Uiso 0.9095(12) 1 calc R . . A 1
H2AB H 0.395037 0.743260 0.996333 0.041 Uiso 0.9095(12) 1 calc R . . A 1
C3A C 0.4230(2) 0.66815(17) 0.8508(5) 0.0268(7) Uani 0.9095(12) 1 d D . . A 1
C4A C 0.46335(17) 0.70416(16) 0.7498(4) 0.0270(6) Uani 0.9095(12) 1 d D . . A 1
H4A H 0.456692 0.751304 0.743457 0.032 Uiso 0.9095(12) 1 calc R . . A 1
C5A C 0.51338(15) 0.67364(15) 0.6573(3) 0.0253(6) Uani 0.9095(12) 1 d D . . A 1
H5A H 0.540317 0.699830 0.588743 0.030 Uiso 0.9095(12) 1 calc R . . A 1
C6A C 0.52411(15) 0.60499(15) 0.6647(3) 0.0223(6) Uani 0.9095(12) 1 d D . . A 1
C7A C 0.4833(3) 0.56832(16) 0.7664(7) 0.0290(7) Uani 0.9095(12) 1 d D . . A 1
H7A H 0.489676 0.521153 0.773065 0.035 Uiso 0.9095(12) 1 calc R . . A 1
C8A C 0.43382(16) 0.59963(17) 0.8574(4) 0.0308(7) Uani 0.9095(12) 1 d D . . A 1
H8A H 0.406658 0.573619 0.925875 0.037 Uiso 0.9095(12) 1 calc R . . A 1
C9A C 0.59281(15) 0.59979(14) 0.4318(3) 0.0235(6) Uani 0.9095(12) 1 d D . . A 1
C10A C 0.53882(15) 0.61439(14) 0.3298(3) 0.0261(6) Uani 0.9095(12) 1 d D . . A
1
H10A H 0.489882 0.605133 0.353947 0.031 Uiso 0.9095(12) 1 calc R . . A 1
C11A C 0.55553(16) 0.64227(14) 0.1935(3) 0.0274(6) Uani 0.9095(12) 1 d D . . A
1
H11A H 0.518385 0.651947 0.123915 0.033 Uiso 0.9095(12) 1 calc R . . A 1
C12A C 0.62703(18) 0.65595(15) 0.1592(3) 0.0249(6) Uani 0.9095(12) 1 d D . . A
1
C13A C 0.68192(16) 0.64067(15) 0.2577(3) 0.0278(6) Uani 0.9095(12) 1 d D . . A
1
H13A H 0.730836 0.649563 0.232742 0.033 Uiso 0.9095(12) 1 calc R . . A 1
C14A C 0.66439(16) 0.61209(15) 0.3939(4) 0.0277(6) Uani 0.9095(12) 1 d D . . A
1
H14A H 0.701738 0.600853 0.461809 0.033 Uiso 0.9095(12) 1 calc R . . A 1
C15A C 0.62024(15) 0.52114(14) 0.6326(3) 0.0245(6) Uani 0.9095(12) 1 d D . . A
1
C16A C 0.63720(16) 0.46569(16) 0.5452(4) 0.0291(6) Uani 0.9095(12) 1 d D . . A
1
H16A H 0.618593 0.462154 0.447211 0.035 Uiso 0.9095(12) 1 calc R . . A 1
C17A C 0.6812(2) 0.41587(18) 0.6016(4) 0.0355(9) Uani 0.9095(12) 1 d D . . A 1
H17A H 0.693302 0.378407 0.541416 0.043 Uiso 0.9095(12) 1 calc R . . A 1
C18A C 0.7078(2) 0.42001(19) 0.7447(5) 0.0394(9) Uani 0.9095(12) 1 d D . . A 1
H18A H 0.737472 0.385312 0.783307 0.047 Uiso 0.9095(12) 1 calc R . . A 1
C19A C 0.69076(19) 0.47502(19) 0.8314(4) 0.0389(9) Uani 0.9095(12) 1 d D . . A
1
H19A H 0.709012 0.478049 0.929756 0.047 Uiso 0.9095(12) 1 calc R . . A 1
C20A C 0.64743(18) 0.52565(17) 0.7761(4) 0.0325(7) Uani 0.9095(12) 1 d D . . A
1
H20A H 0.636270 0.563438 0.836096 0.039 Uiso 0.9095(12) 1 calc R . . A 1
Br1B Br 0.2772(3) 0.2764(3) 0.8544(7) 0.0751(19) Uani 0.0905(12) 1 d D . . A 2
O1B O 0.250000 0.750000 1.0881(3) 0.0331(6) Uani 0.0905(12) 2 d DS T P A 2
N1B N 0.3094(8) 0.7541(13) 0.862(2) 0.0198(5) Uani 0.0905(12) 1 d D . . A 2
N2B N 0.4960(8) 0.4935(7) 0.717(2) 0.0274(5) Uani 0.0905(12) 1 d D . . A 2
C1B C 0.250000 0.750000 0.9506(4) 0.0225(7) Uani 0.0905(12) 2 d DS T P A 2
C2B C 0.3847(10) 0.7496(13) 0.906(3) 0.0343(8) Uani 0.0905(12) 1 d D . . A 2
H2BA H 0.388350 0.753477 1.014949 0.041 Uiso 0.0905(12) 1 calc R . . A 2
H2BB H 0.411938 0.787387 0.861168 0.041 Uiso 0.0905(12) 1 calc R . . A 2
C3B C 0.418(2) 0.6841(12) 0.856(6) 0.0268(7) Uani 0.0905(12) 1 d D . . A 2
C4B C 0.3914(14) 0.6258(11) 0.917(3) 0.0308(7) Uani 0.0905(12) 1 d D . . A 2
H4B H 0.355563 0.627787 0.992247 0.037 Uiso 0.0905(12) 1 calc R . . A 2
C5B C 0.4166(14) 0.5644(12) 0.869(3) 0.0308(7) Uani 0.0905(12) 1 d D . . A 2
H5B H 0.392937 0.524946 0.902715 0.037 Uiso 0.0905(12) 1 calc R . . A 2
C6B C 0.475(3) 0.5577(9) 0.774(7) 0.0290(7) Uani 0.0905(12) 1 d D . . A 2
C7B C 0.5040(14) 0.6166(10) 0.718(3) 0.0223(6) Uani 0.0905(12) 1 d D . . A 2
H7B H 0.544002 0.614560 0.652250 0.027 Uiso 0.0905(12) 1 calc R . . A 2
C8B C 0.4752(16) 0.6789(11) 0.758(4) 0.0270(6) Uani 0.0905(12) 1 d D . . A 2
H8B H 0.495288 0.718466 0.715868 0.032 Uiso 0.0905(12) 1 calc R . . A 2
C9B C 0.4436(8) 0.4428(7) 0.7468(16) 0.0261(6) Uani 0.0905(12) 1 d D . . A 2
C10B C 0.4570(10) 0.3974(8) 0.860(2) 0.0274(6) Uani 0.0905(12) 1 d D . . A 2
H10B H 0.500116 0.399874 0.916486 0.033 Uiso 0.0905(12) 1 calc R . . A 2
C11B C 0.4067(7) 0.3490(9) 0.888(2) 0.0249(6) Uani 0.0905(12) 1 d D . . A 2
H11B H 0.415362 0.317481 0.964900 0.030 Uiso 0.0905(12) 1 calc R . . A 2
C12B C 0.3438(8) 0.3447(6) 0.8069(16) 0.0278(6) Uani 0.0905(12) 1 d D . . A 2
C13B C 0.3284(11) 0.3883(7) 0.695(2) 0.0277(6) Uani 0.0905(12) 1 d D . . A 2
H13B H 0.285029 0.385248 0.638559 0.033 Uiso 0.0905(12) 1 calc R . . A 2
C14B C 0.3801(9) 0.4375(9) 0.667(2) 0.0235(6) Uani 0.0905(12) 1 d D . . A 2
H14B H 0.371355 0.468852 0.589364 0.028 Uiso 0.0905(12) 1 calc R . . A 2
C15B C 0.5701(9) 0.4772(11) 0.730(3) 0.035(8) Uani 0.0905(12) 1 d D . . A 2
C16B C 0.6203(13) 0.5159(16) 0.808(4) 0.0325(7) Uani 0.0905(12) 1 d D . . A 2
H16B H 0.605390 0.555082 0.859173 0.039 Uiso 0.0905(12) 1 calc R . . A 2
C17B C 0.6918(14) 0.4966(19) 0.809(5) 0.0389(9) Uani 0.0905(12) 1 d D . . A 2
H17B H 0.724992 0.521066 0.868005 0.047 Uiso 0.0905(12) 1 calc R . . A 2
C18B C 0.7168(15) 0.4429(17) 0.727(5) 0.0394(9) Uani 0.0905(12) 1 d D . . A 2
H18B H 0.766250 0.430238 0.729710 0.047 Uiso 0.0905(12) 1 calc R . . A 2
C19B C 0.6681(13) 0.4084(19) 0.640(5) 0.0355(9) Uani 0.0905(12) 1 d D . . A 2
H19B H 0.684334 0.372531 0.579564 0.043 Uiso 0.0905(12) 1 calc R . . A 2
C20B C 0.5958(12) 0.4252(13) 0.642(3) 0.0291(6) Uani 0.0905(12) 1 d D . . A 2
H20B H 0.563033 0.400821 0.580988 0.035 Uiso 0.0905(12) 1 calc R . . A 2
H1A H 0.3045(17) 0.7312(14) 0.7845(19) 0.028(8) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C1A N1A C2A 119.8(2) . .
C1A N1A H1A 114(2) . .
C2A N1A H1A 124(2) . .
C6A N2A C9A 120.0(2) . .
C6A N2A C15A 120.2(2) . .
C9A N2A C15A 118.6(2) . .
O1A C1A N1A 120.77(16) . 2_565
O1A C1A N1A 120.77(16) . .
N1A C1A N1A 118.5(3) 2_565 .
N1A C2A H2AA 109.3 . .
N1A C2A H2AB 109.3 . .
N1A C2A C3A 111.5(3) . .
H2AA C2A H2AB 108.0 . .
C3A C2A H2AA 109.3 . .
C3A C2A H2AB 109.3 . .
C4A C3A C2A 120.3(3) . .
C4A C3A C8A 117.7(3) . .
C8A C3A C2A 122.0(3) . .
C3A C4A H4A 119.0 . .
C3A C4A C5A 122.0(3) . .
C5A C4A H4A 119.0 . .
C4A C5A H5A 120.0 . .
C6A C5A C4A 120.0(3) . .
C6A C5A H5A 120.0 . .
C5A C6A N2A 121.4(3) . .
C5A C6A C7A 118.2(3) . .
C7A C6A N2A 120.4(3) . .
C6A C7A H7A 119.6 . .
C8A C7A C6A 120.9(3) . .
C8A C7A H7A 119.6 . .
C3A C8A H8A 119.4 . .
C7A C8A C3A 121.3(3) . .
C7A C8A H8A 119.4 . .
C10A C9A N2A 120.6(3) . .
C10A C9A C14A 119.2(3) . .
C14A C9A N2A 120.3(3) . .
C9A C10A H10A 119.7 . .
C11A C10A C9A 120.7(3) . .
C11A C10A H10A 119.7 . .
C10A C11A H11A 120.3 . .
C10A C11A C12A 119.4(3) . .
C12A C11A H11A 120.3 . .
C11A C12A Br1A 119.4(2) . .
C13A C12A Br1A 119.5(2) . .
C13A C12A C11A 121.1(3) . .
C12A C13A H13A 120.5 . .
C12A C13A C14A 119.0(3) . .
C14A C13A H13A 120.5 . .
C9A C14A C13A 120.7(3) . .
C9A C14A H14A 119.6 . .
C13A C14A H14A 119.6 . .
C16A C15A N2A 119.4(3) . .
C20A C15A N2A 120.9(3) . .
C20A C15A C16A 119.7(3) . .
C15A C16A H16A 120.1 . .
C17A C16A C15A 119.7(3) . .
C17A C16A H16A 120.1 . .
C16A C17A H17A 119.7 . .
C16A C17A C18A 120.6(3) . .
C18A C17A H17A 119.7 . .
C17A C18A H18A 120.2 . .
C17A C18A C19A 119.5(3) . .
C19A C18A H18A 120.2 . .
C18A C19A H19A 119.7 . .
C20A C19A C18A 120.6(3) . .
C20A C19A H19A 119.7 . .
C15A C20A H20A 120.1 . .
C19A C20A C15A 119.9(3) . .
C19A C20A H20A 120.1 . .
Br1B Br1B C12B 166.8(5) 2 .
C1B N1B C2B 127.6(18) . .
C1B N1B H1A 112(3) . .
C2B N1B H1A 107(3) . .
C9B N2B C6B 112.2(12) . .
C15B N2B C6B 116(2) . .
C15B N2B C9B 118.6(15) . .
O1B C1B N1B 126.0(9) . .
O1B C1B N1B 126.0(9) . 2_565
N1B C1B N1B 107.9(17) . 2_565
N1B C2B H2BA 109.4 . .
N1B C2B H2BB 109.4 . .
N1B C2B C3B 111(2) . .
H2BA C2B H2BB 108.0 . .
C3B C2B H2BA 109.4 . .
C3B C2B H2BB 109.4 . .
C4B C3B C2B 117.9(19) . .
C4B C3B C8B 117.7(17) . .
C8B C3B C2B 124.4(19) . .
C3B C4B H4B 119.8 . .
C3B C4B C5B 120.3(19) . .
C5B C4B H4B 119.8 . .
C4B C5B H5B 118.6 . .
C4B C5B C6B 122.9(19) . .
C6B C5B H5B 118.6 . .
C5B C6B N2B 121.4(17) . .
C5B C6B C7B 116.5(16) . .
C7B C6B N2B 121(2) . .
C6B C7B H7B 119.6 . .
C6B C7B C8B 120.8(18) . .
C8B C7B H7B 119.6 . .
C3B C8B C7B 121.4(19) . .
C3B C8B H8B 119.3 . .
C7B C8B H8B 119.3 . .
C10B C9B N2B 118.9(14) . .
C14B C9B N2B 122.1(14) . .
C14B C9B C10B 119.0(14) . .
C9B C10B H10B 120.7 . .
C11B C10B C9B 118.5(17) . .
C11B C10B H10B 120.7 . .
C10B C11B H11B 119.2 . .
C10B C11B C12B 121.6(17) . .
C12B C11B H11B 119.2 . .
C11B C12B Br1B 118.6(10) . .
C13B C12B Br1B 119.4(10) . .
C13B C12B C11B 122.0(15) . .
C12B C13B H13B 122.0 . .
C12B C13B C14B 116.0(17) . .
C14B C13B H13B 122.0 . .
C9B C14B C13B 123.0(17) . .
C9B C14B H14B 118.5 . .
C13B C14B H14B 118.5 . .
C16B C15B N2B 124.0(17) . .
C20B C15B N2B 117.2(16) . .
C20B C15B C16B 118.1(16) . .
C15B C16B H16B 120.4 . .
C17B C16B C15B 119(2) . .
C17B C16B H16B 120.4 . .
C16B C17B H17B 118.8 . .
C16B C17B C18B 122(2) . .
C18B C17B H17B 118.8 . .
C17B C18B H18B 121.0 . .
C19B C18B C17B 118(2) . .
C19B C18B H18B 121.0 . .
C18B C19B H19B 119.6 . .
C18B C19B C20B 121(2) . .
C20B C19B H19B 119.6 . .
C15B C20B H20B 119.4 . .
C19B C20B C15B 121.2(19) . .
C19B C20B H20B 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1A C12A 1.900(3) .
O1A C1A 1.238(4) .
N1A C1A 1.349(3) .
N1A C2A 1.455(4) .
N1A H1A 0.817(17) .
N2A C6A 1.413(4) .
N2A C9A 1.423(4) .
N2A C15A 1.424(4) .
C2A H2AA 0.9900 .
C2A H2AB 0.9900 .
C2A C3A 1.504(4) .
C3A C4A 1.379(5) .
C3A C8A 1.383(5) .
C4A H4A 0.9500 .
C4A C5A 1.387(4) .
C5A H5A 0.9500 .
C5A C6A 1.385(4) .
C6A C7A 1.394(4) .
C7A H7A 0.9500 .
C7A C8A 1.379(5) .
C8A H8A 0.9500 .
C9A C10A 1.388(4) .
C9A C14A 1.391(4) .
C10A H10A 0.9500 .
C10A C11A 1.383(4) .
C11A H11A 0.9500 .
C11A C12A 1.387(5) .
C12A C13A 1.383(4) .
C13A H13A 0.9500 .
C13A C14A 1.391(4) .
C14A H14A 0.9500 .
C15A C16A 1.393(4) .
C15A C20A 1.390(5) .
C16A H16A 0.9500 .
C16A C17A 1.382(5) .
C17A H17A 0.9500 .
C17A C18A 1.382(5) .
C18A H18A 0.9500 .
C18A C19A 1.383(6) .
C19A H19A 0.9500 .
C19A C20A 1.382(5) .
C20A H20A 0.9500 .
Br1B Br1B 1.458(10) 2
Br1B C12B 1.886(13) .
O1B C1B 1.238(4) .
N1B C1B 1.363(13) .
N1B C2B 1.454(14) .
N1B H1A 0.836(18) .
N2B C6B 1.434(14) .
N2B C9B 1.427(13) .
N2B C15B 1.417(13) .
C2B H2BA 0.9900 .
C2B H2BB 0.9900 .
C2B C3B 1.512(14) .
C3B C4B 1.376(16) .
C3B C8B 1.387(15) .
C4B H4B 0.9500 .
C4B C5B 1.380(15) .
C5B H5B 0.9500 .
C5B C6B 1.383(15) .
C6B C7B 1.387(14) .
C7B H7B 0.9500 .
C7B C8B 1.397(15) .
C8B H8B 0.9500 .
C9B C10B 1.384(14) .
C9B C14B 1.383(14) .
C10B H10B 0.9500 .
C10B C11B 1.364(14) .
C11B H11B 0.9500 .
C11B C12B 1.376(15) .
C12B C13B 1.364(15) .
C13B H13B 0.9500 .
C13B C14B 1.395(14) .
C14B H14B 0.9500 .
C15B C16B 1.398(15) .
C15B C20B 1.388(14) .
C16B H16B 0.9500 .
C16B C17B 1.378(15) .
C17B H17B 0.9500 .
C17B C18B 1.380(16) .
C18B H18B 0.9500 .
C18B C19B 1.376(16) .
C19B H19B 0.9500 .
C19B C20B 1.380(15) .
C20B H20B 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.817(17) 2.07(2) 2.823(3) 153(3) 7_575 yes
N1B H1A O1B 0.836(18) 2.07(2) 2.70(2) 131(3) 7_575 yes
