#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557398.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_1557398
loop_
_publ_author_name
'Yuan, K.'
'Kahan, R. J.'
'Si, C.'
'Williams, A.'
'Kirschner, S.'
'Uzelac, M.'
'Zysman-Colman, E.'
'Ingleson, M. J.'
_publ_section_title
;
 The synthesis of brominated-boron-doped PAHs by alkyne 1,1-bromoboration:
 mechanistic and functionalisation studies
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              3258
_journal_page_last               3267
_journal_paper_doi               10.1039/C9SC05404A
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C22 H26 B Br O2'
_chemical_formula_sum            'C22 H26 B Br O2'
_chemical_formula_weight         413.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-25 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.511(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4265(4)
_cell_length_b                   15.8695(10)
_cell_length_c                   20.6170(11)
_cell_measurement_reflns_used    4753
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      27.2530
_cell_measurement_theta_min      4.0710
_cell_volume                     2084.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  59.00   1.00   15.00    --   10.52-127.00  99.00   52
  2  ω     22.00  47.00   1.00   15.00    --   10.52-143.00 -70.00   25
  3  ω    -15.00  31.00   1.00   15.00    --   -9.35 -99.00  30.00   46
  4  ω     -5.00  21.00   1.00   15.00    --   10.52 -99.00 150.00   26
  5  ω    -23.00  89.00   1.00   15.00    --   10.52  19.00 -30.00  112
  6  ω    -28.00  33.00   1.00   15.00    --   10.52 -77.00 -30.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0235783000
_diffrn_orient_matrix_UB_12      -0.0326918000
_diffrn_orient_matrix_UB_13      0.0232641000
_diffrn_orient_matrix_UB_21      0.0165193000
_diffrn_orient_matrix_UB_22      0.0303731000
_diffrn_orient_matrix_UB_23      0.0253839000
_diffrn_orient_matrix_UB_31      -0.1075645000
_diffrn_orient_matrix_UB_32      -0.0025045000
_diffrn_orient_matrix_UB_33      0.0042851000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18476
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        27.483
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.222
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.984
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4679
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0481
_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)+(0.0133P)²+2.7772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3693
_reflns_number_total             4679
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc05404a2.cif
_cod_data_source_block           mi19006_refinalized
_cod_depositor_comments
;Adding full bibliography for 1557396--1557406.cif.

 Adding full bibliography for 1557396--1557406.cif.
;
_cod_database_code               1557398
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H26 B Br O2'
_chemical_oxdiff_usercomment     '@ 120 K KY161'
_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 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C1A, C2A, C19A, C20A, C21A, C22A, C1B, C2B, C19B, C20B, C21B, C22B
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
3. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C1B \\sim C2B
\\sim C19B \\sim C20B \\sim C21B \\sim C22B: within 2A with sigma of 0.012 and
sigma for terminal atoms of 0.024
4. Others
 Sof(C1B)=Sof(C2B)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20B)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22B)=
 Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22A)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C8(H8), C7(H7), C9(H9), C14(H14), C13(H13), C11(H11)
5.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C19A(H19A,H19B,H19C), C20A(H20A,
 H20B,H20C), C21A(H21A,H21B,H21C), C22A(H22A,H22B,H22C), C19B(H19D,H19E,H19F),
 C20B(H20D,H20E,H20F), C21B(H21D,H21E,H21F), C22B(H22D,H22E,H22F)
;
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.779
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.12357(5) 0.78691(2) 0.23761(2) 0.03796(11) Uani 1 1 d . . . . .
B1 B 0.2870(5) 0.6740(2) 0.14929(15) 0.0225(7) Uani 1 1 d . . . . .
O1 O 0.2149(3) 0.59966(15) 0.12527(15) 0.0589(8) Uani 1 1 d . . . . .
O2 O 0.4852(3) 0.67082(13) 0.17862(13) 0.0475(6) Uani 1 1 d . . . . .
C5 C -0.4253(4) 0.92444(17) 0.13890(14) 0.0254(6) Uani 1 1 d . . . . .
H5 H -0.544136 0.916301 0.159504 0.031 Uiso 1 1 calc R . . . .
C4 C -0.2827(4) 0.85897(17) 0.13726(13) 0.0238(6) Uani 1 1 d . . . . .
H4 H -0.305496 0.807954 0.157386 0.029 Uiso 1 1 calc R . . . .
C3 C -0.1059(4) 0.86931(16) 0.10568(13) 0.0210(6) Uani 1 1 d . . . . .
C6 C -0.3938(4) 1.00186(17) 0.11031(13) 0.0242(6) Uani 1 1 d . . . . .
C8 C -0.0745(4) 0.94682(17) 0.07689(13) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.042462 0.954688 0.055373 0.031 Uiso 1 1 calc R . . . .
C7 C -0.2150(4) 1.01232(17) 0.07985(14) 0.0268(6) Uani 1 1 d . . . . .
H7 H -0.189508 1.064041 0.061195 0.032 Uiso 1 1 calc R . . . .
C9 C -0.0879(4) 0.77560(17) -0.01876(13) 0.0240(6) Uani 1 1 d . . . . .
H9 H -0.221249 0.789795 -0.009487 0.029 Uiso 1 1 calc R . . . .
C10 C 0.0802(4) 0.77640(16) 0.03131(12) 0.0207(6) Uani 1 1 d . . . . .
C14 C 0.2780(4) 0.75575(17) 0.01546(13) 0.0241(6) Uani 1 1 d . . . . .
H14 H 0.393393 0.757075 0.047761 0.029 Uiso 1 1 calc R . . . .
C13 C 0.3051(4) 0.73314(17) -0.04807(14) 0.0252(6) Uani 1 1 d . . . . .
H13 H 0.438211 0.718525 -0.057363 0.030 Uiso 1 1 calc R . . . .
C11 C -0.0597(4) 0.75407(18) -0.08195(13) 0.0262(6) Uani 1 1 d . . . . .
H11 H -0.174399 0.754304 -0.114516 0.031 Uiso 1 1 calc R . . . .
C12 C 0.1376(4) 0.73198(17) -0.09783(13) 0.0244(6) Uani 1 1 d . . . . .
C15 C 0.1682(5) 0.7086(2) -0.16676(14) 0.0365(7) Uani 1 1 d . . . . .
H15A H 0.315442 0.703052 -0.169684 0.055 Uiso 1 1 calc GR . . . .
H15B H 0.109768 0.751852 -0.196254 0.055 Uiso 1 1 calc GR . . . .
H15C H 0.098948 0.656109 -0.178270 0.055 Uiso 1 1 calc GR . . . .
C16 C -0.5504(5) 1.07281(19) 0.11161(16) 0.0354(7) Uani 1 1 d . . . . .
H16A H -0.480494 1.121737 0.131275 0.053 Uiso 1 1 calc GR . . . .
H16B H -0.659124 1.055826 0.136668 0.053 Uiso 1 1 calc GR . . . .
H16C H -0.611132 1.085885 0.067726 0.053 Uiso 1 1 calc GR . . . .
C18 C 0.0446(4) 0.79870(16) 0.09936(13) 0.0209(6) Uani 1 1 d . . . . .
C17 C 0.1461(4) 0.75542(18) 0.14875(13) 0.0236(6) Uani 1 1 d . . . . .
C1A C 0.3768(10) 0.5339(4) 0.1646(4) 0.0282(13) Uani 0.472(6) 1 d . U P A 1
C2A C 0.5785(12) 0.5856(4) 0.1612(4) 0.0285(14) Uani 0.472(6) 1 d . U P A 1
C19A C 0.753(2) 0.5700(17) 0.2159(6) 0.040(3) Uani 0.472(6) 1 d . U P A 1
H19A H 0.707550 0.585219 0.256863 0.060 Uiso 0.472(6) 1 calc GR . P A 1
H19B H 0.872910 0.603532 0.209087 0.060 Uiso 0.472(6) 1 calc GR . P A 1
H19C H 0.790961 0.511483 0.216719 0.060 Uiso 0.472(6) 1 calc GR . P A 1
C20A C 0.6572(12) 0.5831(5) 0.0946(4) 0.0386(18) Uani 0.472(6) 1 d . U P A 1
H20A H 0.720645 0.529301 0.088722 0.058 Uiso 0.472(6) 1 calc GR . P A 1
H20B H 0.759153 0.626832 0.092364 0.058 Uiso 0.472(6) 1 calc GR . P A 1
H20C H 0.541456 0.591473 0.060800 0.058 Uiso 0.472(6) 1 calc GR . P A 1
C21A C 0.3417(14) 0.5158(5) 0.2357(4) 0.0396(19) Uani 0.472(6) 1 d . U P A 1
H21A H 0.443355 0.475483 0.254527 0.059 Uiso 0.472(6) 1 calc GR . P A 1
H21B H 0.203024 0.493599 0.236292 0.059 Uiso 0.472(6) 1 calc GR . P A 1
H21C H 0.356743 0.567112 0.260533 0.059 Uiso 0.472(6) 1 calc GR . P A 1
C22A C 0.359(3) 0.4567(14) 0.1247(13) 0.040(3) Uani 0.472(6) 1 d . U P A 1
H22A H 0.475547 0.420394 0.138389 0.060 Uiso 0.472(6) 1 calc GR . P A 1
H22B H 0.357910 0.471211 0.079465 0.060 Uiso 0.472(6) 1 calc GR . P A 1
H22C H 0.230332 0.428181 0.130216 0.060 Uiso 0.472(6) 1 calc GR . P A 1
C1B C 0.3994(9) 0.5469(4) 0.1236(3) 0.0304(13) Uani 0.528(6) 1 d . U P A 2
C2B C 0.5210(11) 0.5782(4) 0.1889(3) 0.0287(12) Uani 0.528(6) 1 d . U P A 2
C19B C 0.760(2) 0.5684(15) 0.1951(5) 0.045(3) Uani 0.528(6) 1 d . U P A 2
H19D H 0.812683 0.597229 0.159655 0.068 Uiso 0.528(6) 1 calc GR . P A 2
H19E H 0.795605 0.509661 0.193754 0.068 Uiso 0.528(6) 1 calc GR . P A 2
H19F H 0.822876 0.592070 0.235939 0.068 Uiso 0.528(6) 1 calc GR . P A 2
C20B C 0.4391(12) 0.5440(5) 0.2498(3) 0.0371(17) Uani 0.528(6) 1 d . U P A 2
H20D H 0.507351 0.572607 0.287727 0.056 Uiso 0.528(6) 1 calc GR . P A 2
H20E H 0.467898 0.484737 0.253585 0.056 Uiso 0.528(6) 1 calc GR . P A 2
H20F H 0.290365 0.553135 0.246319 0.056 Uiso 0.528(6) 1 calc GR . P A 2
C21B C 0.5194(13) 0.5577(5) 0.0649(3) 0.052(2) Uani 0.528(6) 1 d . U P A 2
H21D H 0.424405 0.551547 0.025225 0.078 Uiso 0.528(6) 1 calc GR . P A 2
H21E H 0.627223 0.515608 0.066474 0.078 Uiso 0.528(6) 1 calc GR . P A 2
H21F H 0.581989 0.612688 0.066221 0.078 Uiso 0.528(6) 1 calc GR . P A 2
C22B C 0.308(3) 0.4572(12) 0.1238(14) 0.047(3) Uani 0.528(6) 1 d . U P A 2
H22D H 0.214786 0.453386 0.156576 0.071 Uiso 0.528(6) 1 calc GR . P A 2
H22E H 0.419562 0.417237 0.133252 0.071 Uiso 0.528(6) 1 calc GR . P A 2
H22F H 0.231070 0.445059 0.081639 0.071 Uiso 0.528(6) 1 calc GR . P A 2
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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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
0 -15 -21 0.0443
-1 14 22 0.0350
0 18 -17 0.0348
0 -18 17 0.0248
9 -3 -3 0.1586
-9 0 6 0.1821
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
O1 B1 C17 123.3(3) . . ?
O2 B1 O1 113.4(3) . . ?
O2 B1 C17 123.1(3) . . ?
B1 O1 C1A 102.4(3) . . ?
B1 O1 C1B 105.8(3) . . ?
B1 O2 C2A 107.7(3) . . ?
B1 O2 C2B 102.7(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C4 C3 C8 118.5(2) . . ?
C4 C3 C18 121.9(2) . . ?
C8 C3 C18 119.6(2) . . ?
C5 C6 C16 121.1(2) . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 C16 120.7(3) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 C3 120.9(2) . . ?
C7 C8 H8 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C10 C9 H9 119.5 . . ?
C11 C9 H9 119.5 . . ?
C11 C9 C10 121.1(3) . . ?
C9 C10 C18 119.9(2) . . ?
C14 C10 C9 117.9(2) . . ?
C14 C10 C18 122.2(2) . . ?
C10 C14 H14 119.6 . . ?
C13 C14 C10 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.4 . . ?
C9 C11 H11 119.4 . . ?
C9 C11 C12 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 117.7(2) . . ?
C13 C12 C15 121.1(2) . . ?
C11 C12 C15 121.2(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C18 C3 116.1(2) . . ?
C17 C18 C3 125.4(2) . . ?
C17 C18 C10 118.5(2) . . ?
B1 C17 Br1 108.71(19) . . ?
C18 C17 Br1 120.4(2) . . ?
C18 C17 B1 130.8(3) . . ?
C2A C1A O1 97.1(5) . . ?
C21A C1A O1 115.7(5) . . ?
C21A C1A C2A 111.7(7) . . ?
C22A C1A O1 105.0(11) . . ?
C22A C1A C2A 115.0(9) . . ?
C22A C1A C21A 111.5(11) . . ?
O2 C2A C1A 95.8(5) . . ?
C19A C2A O2 104.2(11) . . ?
C19A C2A C1A 115.4(10) . . ?
C19A C2A C20A 111.6(8) . . ?
C20A C2A O2 114.7(6) . . ?
C20A C2A C1A 114.0(7) . . ?
C2A C19A H19A 109.5 . . ?
C2A C19A H19B 109.5 . . ?
C2A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C2A C20A H20A 109.5 . . ?
C2A C20A H20B 109.5 . . ?
C2A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C1A C21A H21A 109.5 . . ?
C1A C21A H21B 109.5 . . ?
C1A C21A H21C 109.5 . . ?
H21A C21A H21B 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C1A C22A H22A 109.5 . . ?
C1A C22A H22B 109.5 . . ?
C1A C22A H22C 109.5 . . ?
H22A C22A H22B 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O1 C1B C2B 96.6(4) . . ?
O1 C1B C21B 116.9(5) . . ?
O1 C1B C22B 102.6(9) . . ?
C21B C1B C2B 113.8(6) . . ?
C21B C1B C22B 109.8(11) . . ?
C22B C1B C2B 116.4(11) . . ?
O2 C2B C1B 98.1(4) . . ?
O2 C2B C19B 104.2(10) . . ?
O2 C2B C20B 113.7(5) . . ?
C19B C2B C1B 115.3(8) . . ?
C20B C2B C1B 114.4(6) . . ?
C20B C2B C19B 110.2(7) . . ?
C2B C19B H19D 109.5 . . ?
C2B C19B H19E 109.5 . . ?
C2B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C2B C20B H20D 109.5 . . ?
C2B C20B H20E 109.5 . . ?
C2B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C1B C21B H21D 109.5 . . ?
C1B C21B H21E 109.5 . . ?
C1B C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C1B C22B H22D 109.5 . . ?
C1B C22B H22E 109.5 . . ?
C1B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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 C17 1.923(3) . ?
B1 O1 1.339(4) . ?
B1 O2 1.338(4) . ?
B1 C17 1.577(4) . ?
O1 C1A 1.615(7) . ?
O1 C1B 1.455(6) . ?
O2 C2A 1.541(7) . ?
O2 C2B 1.498(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(4) . ?
C5 C6 1.389(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.391(4) . ?
C3 C8 1.392(4) . ?
C3 C18 1.497(4) . ?
C6 C7 1.389(4) . ?
C6 C16 1.513(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.383(4) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.393(4) . ?
C9 C11 1.381(4) . ?
C10 C14 1.392(4) . ?
C10 C18 1.493(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(4) . ?
C12 C15 1.506(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C17 1.327(4) . ?
C1A C2A 1.543(10) . ?
C1A C21A 1.539(10) . ?
C1A C22A 1.47(2) . ?
C2A C19A 1.504(17) . ?
C2A C20A 1.526(10) . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C1B C2B 1.548(10) . ?
C1B C21B 1.526(9) . ?
C1B C22B 1.542(17) . ?
C2B C19B 1.536(16) . ?
C2B C20B 1.524(10) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306156
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.4254 -14.7739 -21.4261 -0.0255 -0.9996 -0.0091
-1.2620 14.2494 22.3893 0.0253 0.9803 0.1960
0.3023 18.1836 -16.8885 -0.9802 0.1286 -0.1504
-0.2179 -18.1966 16.8427 0.9816 -0.1288 0.1412
8.9605 -3.2550 -3.1415 0.2446 -0.0306 -0.9691
-9.0204 -0.2842 6.4293 -0.0538 0.0056 0.9985
