#------------------------------------------------------------------------------
#$Date: 2021-05-19 04:00:19 +0300 (Wed, 19 May 2021) $
#$Revision: 265321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/26/1562680.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_1562680
loop_
_publ_author_name
'Hess, Andreas'
'Prohaska, Jan Philip'
'Doerrich, Sabrina Bettina'
'Trauner, Florian'
'Lutter, Ferdinand Hermann'
'Lemaire, Sébastien'
'Wagschal, Simon'
'Karaghiosoff, Konstantin'
'Knochel, Paul'
_publ_section_title
;
 Directed Regioselective ortho,ortho’-Magnesiations of Aromatics
 and Heterocycles using sBu2Mg in Toluene
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01777B
_journal_year                    2021
_chemical_formula_moiety         'C21 H24 Br N3 O5 Si'
_chemical_formula_sum            'C21 H24 Br N3 O5 Si'
_chemical_formula_weight         506.43
_chemical_name_systematic
;
(4-bromo-2,5-dimethoxyphenyl)(5-(4-(trimethylsilyl)-1H-
1,2,3-triazol-1-yl)benzo[d][1,3]dioxol-4-yl)methanol
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2021-02-05 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                105.984(4)
_cell_angle_beta                 104.098(4)
_cell_angle_gamma                96.492(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0355(4)
_cell_length_b                   11.4221(6)
_cell_length_c                   13.0590(5)
_cell_measurement_reflns_used    3471
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.2820
_cell_measurement_theta_min      2.6860
_cell_volume                     1096.49(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.715
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0475
_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)+(0.0426P)²+0.0145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             6683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01777b2.cif
_cod_data_source_block           test1
_cod_original_cell_volume        1096.48(9)
_cod_database_code               1562680
_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   0.546
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2014-3
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 0.01593(4) -0.08437(3) 0.25563(2) 0.03237(10) Uani 1 1 d . . . . .
O1 O 0.4008(2) 0.10350(16) 0.67200(13) 0.0230(4) Uani 1 1 d . . . . .
N1 N 0.5882(2) 0.34801(18) 0.92169(14) 0.0159(4) Uani 1 1 d . . . . .
C1 C 0.4654(3) 0.2575(2) 0.92168(18) 0.0182(5) Uani 1 1 d . . . . .
H1 H 0.3968(19) 0.1889(19) 0.8590(17) 0.022 Uiso 1 1 calc R U . . .
H3 H 0.328(4) 0.505(3) 0.753(3) 0.042(9) Uiso 1 1 d . . . . .
Si1 Si 0.30676(9) 0.20479(6) 1.09033(5) 0.01817(15) Uani 1 1 d . . . . .
N3 N 0.5811(3) 0.38931(19) 1.09027(15) 0.0197(4) Uani 1 1 d . . . . .
O3 O 0.2861(2) 0.45201(16) 0.68978(13) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.4057(3) 0.2588(3) 1.24381(19) 0.0246(6) Uani 1 1 d . . . . .
H3A H 0.415(2) 0.3507(14) 1.2732(5) 0.037 Uiso 1 1 calc R U . . .
H3B H 0.525(2) 0.2385(15) 1.2619(4) 0.037 Uiso 1 1 calc R U . . .
H3C H 0.3305(17) 0.2162(14) 1.2789(6) 0.037 Uiso 1 1 calc R U . . .
C2 C 0.4578(3) 0.2831(2) 1.02950(18) 0.0179(5) Uani 1 1 d . . . . .
O2 O -0.0477(2) 0.17529(17) 0.30945(13) 0.0289(4) Uani 1 1 d . . . . .
N2 N 0.6600(3) 0.42921(18) 1.02565(15) 0.0188(4) Uani 1 1 d . . . . .
O4 O 0.5454(2) 0.38789(17) 0.55076(12) 0.0218(4) Uani 1 1 d . . . . .
C4 C 0.2800(4) 0.0339(2) 1.0315(2) 0.0276(6) Uani 1 1 d . . . . .
H4A H 0.203(2) -0.0056(7) 1.0616(12) 0.041 Uiso 1 1 calc R U . . .
H4B H 0.3901(18) 0.0106(5) 1.0496(13) 0.041 Uiso 1 1 calc R U . . .
H4C H 0.233(2) 0.0097(5) 0.9532(13) 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0921(3) 0.2516(3) 1.0553(2) 0.0277(6) Uani 1 1 d . . . . .
H5A H 0.0470(14) 0.2298(16) 0.9777(13) 0.042 Uiso 1 1 calc R U . . .
H5B H 0.1060(5) 0.3379(14) 1.0870(14) 0.042 Uiso 1 1 calc R U . . .
H5C H 0.0144(15) 0.2110(15) 1.0835(14) 0.042 Uiso 1 1 calc R U . . .
O5 O 0.8449(2) 0.42708(17) 0.58543(13) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.6549(3) 0.3665(2) 0.83311(17) 0.0159(5) Uani 1 1 d . . . . .
C7 C 0.8346(3) 0.3922(2) 0.85513(19) 0.0197(5) Uani 1 1 d . . . . .
H7 H 0.905(2) 0.3954(2) 0.925(2) 0.024 Uiso 1 1 calc R U . . .
C8 C 0.9146(3) 0.4134(2) 0.77673(19) 0.0210(5) Uani 1 1 d . . . . .
H8 H 1.035(4) 0.4313(6) 0.7916(5) 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8033(3) 0.4059(2) 0.67601(18) 0.0172(5) Uani 1 1 d . . . . .
C10 C 0.6838(3) 0.3938(3) 0.5012(2) 0.0340(7) Uani 1 1 d . . . . .
H10A H 0.6766(4) 0.3136(17) 0.4479(12) 0.041 Uiso 1 1 calc R U . . .
H10B H 0.6747(4) 0.4549(13) 0.4621(9) 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5399(3) 0.3605(2) 0.73006(17) 0.0142(4) Uani 1 1 d . . . . .
C11 C 0.6239(3) 0.3814(2) 0.65465(17) 0.0158(5) Uani 1 1 d . . . . .
C13 C 0.3407(3) 0.3404(2) 0.69942(17) 0.0158(5) Uani 1 1 d . . . . .
H13 H 0.3029(11) 0.3193(6) 0.7580(16) 0.019 Uiso 1 1 calc R U . . .
C17 C 0.1072(3) 0.0461(2) 0.39228(18) 0.0216(5) Uani 1 1 d . . . . .
C19 C 0.2897(3) 0.1173(2) 0.57977(18) 0.0183(5) Uani 1 1 d . . . . .
C16 C 0.0669(3) 0.1620(2) 0.40040(18) 0.0198(5) Uani 1 1 d . . . . .
C21 C -0.0557(4) 0.2979(3) 0.3069(2) 0.0275(6) Uani 1 1 d . . . . .
H21A H -0.094(2) 0.3411(9) 0.3672(13) 0.041 Uiso 1 1 calc R U . . .
H21B H -0.135(2) 0.2950(3) 0.2389(13) 0.041 Uiso 1 1 calc R U . . .
H21C H 0.0570(19) 0.3396(9) 0.3129(14) 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4367(4) -0.0165(2) 0.6674(2) 0.0268(6) Uani 1 1 d . . . . .
H20A H 0.3270(18) -0.0741(10) 0.6554(14) 0.040 Uiso 1 1 calc R U . . .
H20B H 0.521(2) -0.0121(4) 0.7382(12) 0.040 Uiso 1 1 calc R U . . .
H20C H 0.487(2) -0.0470(9) 0.6053(13) 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2553(3) 0.2362(2) 0.59051(17) 0.0154(5) Uani 1 1 d . . . . .
C15 C 0.1421(3) 0.2571(2) 0.50114(18) 0.0187(5) Uani 1 1 d . . . . .
H15 H 0.1162(8) 0.335(2) 0.5084(3) 0.022 Uiso 1 1 calc R U . . .
C18 C 0.2162(3) 0.0215(2) 0.48076(19) 0.0209(5) Uani 1 1 d . . . . .
H18 H 0.2381(8) -0.053(2) 0.4742(3) 0.025 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 0.0033 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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C19 O1 C20 118.30(18) . . ?
C1 N1 N2 110.66(18) . . ?
C1 N1 C6 130.78(19) . . ?
N2 N1 C6 118.50(19) . . ?
N1 C1 C2 106.4(2) . . ?
N1 C1 H1 126.8 . . ?
C2 C1 H1 126.8 . . ?
C5 Si1 C4 109.88(13) . . ?
C5 Si1 C3 109.88(12) . . ?
C4 Si1 C3 111.46(12) . . ?
C5 Si1 C2 108.79(12) . . ?
C4 Si1 C2 109.45(11) . . ?
C3 Si1 C2 107.31(11) . . ?
N2 N3 C2 110.58(18) . . ?
C13 O3 H3 106(2) . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 N3 106.1(2) . . ?
C1 C2 Si1 130.52(18) . . ?
N3 C2 Si1 123.26(16) . . ?
C16 O2 C21 117.31(19) . . ?
N3 N2 N1 106.26(18) . . ?
C11 O4 C10 104.30(18) . . ?
Si1 C4 H4A 109.5 . . ?
Si1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si1 C5 H5A 109.5 . . ?
Si1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 O5 C10 104.64(19) . . ?
C7 C6 C12 122.4(2) . . ?
C7 C6 N1 116.74(19) . . ?
C12 C6 N1 120.8(2) . . ?
C6 C7 C8 122.0(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 115.7(2) . . ?
C9 C8 H8 122.2 . . ?
C7 C8 H8 122.2 . . ?
C8 C9 O5 128.3(2) . . ?
C8 C9 C11 122.1(2) . . ?
O5 C9 C11 109.49(19) . . ?
O5 C10 O4 108.9(2) . . ?
O5 C10 H10A 109.9 . . ?
O4 C10 H10A 109.9 . . ?
O5 C10 H10B 109.9 . . ?
O4 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C12 C6 113.8(2) . . ?
C11 C12 C13 119.45(19) . . ?
C6 C12 C13 126.7(2) . . ?
O4 C11 C12 126.2(2) . . ?
O4 C11 C9 109.75(19) . . ?
C12 C11 C9 123.9(2) . . ?
O3 C13 C14 109.19(18) . . ?
O3 C13 C12 109.39(18) . . ?
C14 C13 C12 111.88(18) . . ?
O3 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C16 C17 C18 122.1(2) . . ?
C16 C17 Br1 119.71(18) . . ?
C18 C17 Br1 118.13(19) . . ?
O1 C19 C18 123.5(2) . . ?
O1 C19 C14 115.65(19) . . ?
C18 C19 C14 120.8(2) . . ?
O2 C16 C17 117.6(2) . . ?
O2 C16 C15 124.3(2) . . ?
C17 C16 C15 118.1(2) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 C13 121.2(2) . . ?
C19 C14 C13 119.7(2) . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
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 1.895(2) . ?
O1 C19 1.373(3) . ?
O1 C20 1.421(3) . ?
N1 C1 1.346(3) . ?
N1 N2 1.357(2) . ?
N1 C6 1.442(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.96(3) . ?
Si1 C5 1.852(3) . ?
Si1 C4 1.856(3) . ?
Si1 C3 1.861(2) . ?
Si1 C2 1.876(3) . ?
N3 N2 1.315(3) . ?
N3 C2 1.378(3) . ?
O3 C13 1.422(3) . ?
O3 H3 0.84(3) . ?
C3 H3A 1.001(15) . ?
C3 H3B 1.001(15) . ?
C3 H3C 1.001(15) . ?
O2 C16 1.371(3) . ?
O2 C21 1.419(3) . ?
O4 C11 1.376(3) . ?
O4 C10 1.420(3) . ?
C4 H4A 0.947(15) . ?
C4 H4B 0.947(15) . ?
C4 H4C 0.947(15) . ?
C5 H5A 0.939(15) . ?
C5 H5B 0.939(15) . ?
C5 H5C 0.939(15) . ?
O5 C9 1.379(3) . ?
O5 C10 1.412(3) . ?
C6 C7 1.382(3) . ?
C6 C12 1.413(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.93(3) . ?
C9 C11 1.379(3) . ?
C10 H10A 0.97(2) . ?
C10 H10B 0.97(2) . ?
C12 C11 1.379(3) . ?
C12 C13 1.526(3) . ?
C13 C14 1.522(3) . ?
C13 H13 0.97(3) . ?
C17 C16 1.380(4) . ?
C17 C18 1.386(3) . ?
C19 C18 1.386(3) . ?
C19 C14 1.393(3) . ?
C16 C15 1.398(3) . ?
C21 H21A 0.949(15) . ?
C21 H21B 0.949(15) . ?
C21 H21C 0.949(16) . ?
C20 H20A 0.989(15) . ?
C20 H20B 0.989(15) . ?
C20 H20C 0.989(15) . ?
C14 C15 1.390(3) . ?
C15 H15 0.92(3) . ?
C18 H18 0.87(3) . ?
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
N2 N1 C1 C2 0.6(3) . . . . ?
C6 N1 C1 C2 177.8(2) . . . . ?
N1 C1 C2 N3 -0.8(3) . . . . ?
N1 C1 C2 Si1 174.95(18) . . . . ?
N2 N3 C2 C1 0.7(3) . . . . ?
N2 N3 C2 Si1 -175.44(16) . . . . ?
C5 Si1 C2 C1 -76.1(3) . . . . ?
C4 Si1 C2 C1 44.0(3) . . . . ?
C3 Si1 C2 C1 165.1(2) . . . . ?
C5 Si1 C2 N3 99.0(2) . . . . ?
C4 Si1 C2 N3 -140.9(2) . . . . ?
C3 Si1 C2 N3 -19.8(2) . . . . ?
C2 N3 N2 N1 -0.3(2) . . . . ?
C1 N1 N2 N3 -0.2(2) . . . . ?
C6 N1 N2 N3 -177.82(19) . . . . ?
C1 N1 C6 C7 -131.2(3) . . . . ?
N2 N1 C6 C7 45.8(3) . . . . ?
C1 N1 C6 C12 49.8(3) . . . . ?
N2 N1 C6 C12 -133.2(2) . . . . ?
C12 C6 C7 C8 -0.2(4) . . . . ?
N1 C6 C7 C8 -179.2(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 O5 177.3(2) . . . . ?
C7 C8 C9 C11 1.2(3) . . . . ?
C10 O5 C9 C8 173.9(3) . . . . ?
C10 O5 C9 C11 -9.6(3) . . . . ?
C9 O5 C10 O4 16.5(3) . . . . ?
C11 O4 C10 O5 -17.0(3) . . . . ?
C7 C6 C12 C11 0.5(3) . . . . ?
N1 C6 C12 C11 179.3(2) . . . . ?
C7 C6 C12 C13 -176.2(2) . . . . ?
N1 C6 C12 C13 2.7(3) . . . . ?
C10 O4 C11 C12 -172.3(2) . . . . ?
C10 O4 C11 C9 10.9(3) . . . . ?
C6 C12 C11 O4 -176.2(2) . . . . ?
C13 C12 C11 O4 0.7(3) . . . . ?
C6 C12 C11 C9 0.1(3) . . . . ?
C13 C12 C11 C9 177.1(2) . . . . ?
C8 C9 C11 O4 175.8(2) . . . . ?
O5 C9 C11 O4 -0.9(3) . . . . ?
C8 C9 C11 C12 -1.0(4) . . . . ?
O5 C9 C11 C12 -177.7(2) . . . . ?
C11 C12 C13 O3 -66.7(2) . . . . ?
C6 C12 C13 O3 109.8(2) . . . . ?
C11 C12 C13 C14 54.5(3) . . . . ?
C6 C12 C13 C14 -129.0(2) . . . . ?
C20 O1 C19 C18 -2.7(3) . . . . ?
C20 O1 C19 C14 178.1(2) . . . . ?
C21 O2 C16 C17 -164.7(2) . . . . ?
C21 O2 C16 C15 16.9(3) . . . . ?
C18 C17 C16 O2 -177.5(2) . . . . ?
Br1 C17 C16 O2 3.9(3) . . . . ?
C18 C17 C16 C15 1.1(4) . . . . ?
Br1 C17 C16 C15 -177.54(18) . . . . ?
O1 C19 C14 C15 -179.1(2) . . . . ?
C18 C19 C14 C15 1.6(3) . . . . ?
O1 C19 C14 C13 0.5(3) . . . . ?
C18 C19 C14 C13 -178.7(2) . . . . ?
O3 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -121.8(2) . . . . ?
O3 C13 C14 C19 179.80(19) . . . . ?
C12 C13 C14 C19 58.6(3) . . . . ?
C19 C14 C15 C16 -1.8(3) . . . . ?
C13 C14 C15 C16 178.5(2) . . . . ?
O2 C16 C15 C14 179.0(2) . . . . ?
C17 C16 C15 C14 0.5(4) . . . . ?
O1 C19 C18 C17 -179.3(2) . . . . ?
C14 C19 C18 C17 -0.1(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
Br1 C17 C18 C19 177.35(18) . . . . ?
