#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025431.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_4025431
loop_
_publ_author_name
'Yazhou Wang'
'Haifeng Du'
_publ_section_title
;
 A Copper(II)-Mediated Regioselective Cyclization-Acetoxylation of
 6,8-Dien-1-ones for the Synthesis of Functionalized Cyclopentanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3503
_journal_page_last               3506
_journal_paper_doi               10.1021/jo100413p
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C22 H21 Br O3'
_chemical_formula_sum            'C22 H21 Br O3'
_chemical_formula_weight         413.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.42(3)
_cell_angle_beta                 100.91(3)
_cell_angle_gamma                109.24(3)
_cell_formula_units_Z            4
_cell_length_a                   10.290(2)
_cell_length_b                   11.499(2)
_cell_length_c                   18.124(4)
_cell_measurement_reflns_used    659
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1952.7(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24028
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.16
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  0.6761
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8895
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+1.4223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                7123
_reflns_number_total             8895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100413p_si_002.cif
_cod_data_source_block           sa218
_cod_original_cell_volume        1952.7(7)
_cod_database_code               4025431
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 0.39882(4) 1.23107(3) 0.519922(19) 0.05183(13) Uani 1 1 d . . .
Br1B Br 0.63872(5) -0.20210(3) -0.02353(2) 0.06951(16) Uani 1 1 d . . .
O1A O 0.4274(2) 0.8240(2) 0.18371(14) 0.0455(5) Uani 1 1 d . . .
O1B O 0.5870(2) 0.2006(2) 0.30018(13) 0.0415(5) Uani 1 1 d . . .
O2A O 0.2969(2) 0.67131(18) 0.30677(11) 0.0341(4) Uani 1 1 d . . .
O2B O 0.7433(2) 0.35852(18) 0.19081(11) 0.0357(4) Uani 1 1 d . . .
O3A O 0.1282(2) 0.5988(2) 0.37081(13) 0.0442(5) Uani 1 1 d . . .
O3B O 0.9235(2) 0.4251(2) 0.13399(13) 0.0482(6) Uani 1 1 d . . .
C1A C 0.2756(4) 0.9818(3) 0.19312(18) 0.0444(7) Uani 1 1 d . . .
H1AA H 0.3762 1.0174 0.2087 0.053 Uiso 1 1 calc R . .
C1B C 0.7202(3) 0.0256(3) 0.29911(17) 0.0402(7) Uani 1 1 d . . .
H1BA H 0.6228 -0.0019 0.2735 0.048 Uiso 1 1 calc R . .
C2A C 0.1966(4) 1.0587(3) 0.1947(2) 0.0534(9) Uani 1 1 d . . .
H2AA H 0.2433 1.1467 0.2116 0.064 Uiso 1 1 calc R . .
C2B C 0.7875(4) -0.0598(3) 0.30450(19) 0.0487(8) Uani 1 1 d . . .
H2BA H 0.7365 -0.1458 0.2825 0.058 Uiso 1 1 calc R . .
C3A C 0.0504(5) 1.0083(4) 0.1719(2) 0.0630(11) Uani 1 1 d . . .
H3AA H -0.0033 1.0613 0.1732 0.076 Uiso 1 1 calc R . .
C3B C 0.9290(4) -0.0209(3) 0.3419(2) 0.0538(9) Uani 1 1 d . . .
H3BA H 0.9752 -0.0800 0.3455 0.065 Uiso 1 1 calc R . .
C4A C -0.0175(4) 0.8805(4) 0.1472(2) 0.0622(10) Uani 1 1 d . . .
H4AA H -0.1180 0.8460 0.1311 0.075 Uiso 1 1 calc R . .
C4B C 1.0030(4) 0.1033(3) 0.3738(2) 0.0515(8) Uani 1 1 d . . .
H4BA H 1.1001 0.1298 0.3998 0.062 Uiso 1 1 calc R . .
C5A C 0.0602(3) 0.8017(3) 0.14564(19) 0.0442(7) Uani 1 1 d . . .
H5AA H 0.0128 0.7138 0.1290 0.053 Uiso 1 1 calc R . .
C5B C 0.9366(3) 0.1904(3) 0.36820(18) 0.0400(7) Uani 1 1 d . . .
H5BA H 0.9887 0.2763 0.3899 0.048 Uiso 1 1 calc R . .
C6A C 0.2081(3) 0.8524(3) 0.16867(16) 0.0339(6) Uani 1 1 d . . .
C6B C 0.7943(3) 0.1525(3) 0.33104(16) 0.0327(6) Uani 1 1 d . . .
C7A C 0.2986(3) 0.7741(3) 0.16773(16) 0.0329(6) Uani 1 1 d . . .
C7B C 0.7152(3) 0.2412(3) 0.32481(15) 0.0321(6) Uani 1 1 d . . .
C8A C 0.2301(3) 0.6328(3) 0.14433(16) 0.0354(6) Uani 1 1 d . . .
H8AA H 0.1294 0.6056 0.1486 0.042 Uiso 1 1 calc R . .
C8B C 0.7956(3) 0.3804(3) 0.35288(16) 0.0351(6) Uani 1 1 d . . .
H8BA H 0.8969 0.4010 0.3506 0.042 Uiso 1 1 calc R . .
C9B C 0.7881(5) 0.4173(3) 0.43673(19) 0.0571(9) Uani 1 1 d . . .
H9BA H 0.7099 0.3517 0.4495 0.069 Uiso 1 1 calc R . .
H9BB H 0.8782 0.4279 0.4728 0.069 Uiso 1 1 calc R . .
C9A C 0.2340(6) 0.5911(4) 0.0615(2) 0.0707(13) Uani 1 1 d . . .
H9AA H 0.1447 0.5836 0.0257 0.085 Uiso 1 1 calc R . .
H9AB H 0.3142 0.6531 0.0478 0.085 Uiso 1 1 calc R . .
C10A C 0.2517(5) 0.4664(4) 0.05691(19) 0.0554(9) Uani 1 1 d . . .
H10A H 0.3368 0.4700 0.0379 0.066 Uiso 1 1 calc R . .
H10B H 0.1679 0.4010 0.0213 0.066 Uiso 1 1 calc R . .
C10B C 0.7625(5) 0.5386(4) 0.4418(2) 0.0671(12) Uani 1 1 d . . .
H10C H 0.8327 0.6011 0.4855 0.081 Uiso 1 1 calc R . .
H10D H 0.6664 0.5256 0.4495 0.081 Uiso 1 1 calc R . .
C11A C 0.2679(4) 0.4356(3) 0.13675(17) 0.0405(7) Uani 1 1 d . . .
H11A H 0.3436 0.4003 0.1479 0.049 Uiso 1 1 calc R . .
H11B H 0.1780 0.3744 0.1421 0.049 Uiso 1 1 calc R . .
C11B C 0.7765(4) 0.5850(3) 0.36719(18) 0.0435(7) Uani 1 1 d . . .
H11C H 0.8753 0.6397 0.3705 0.052 Uiso 1 1 calc R . .
H11D H 0.7127 0.6317 0.3539 0.052 Uiso 1 1 calc R . .
C12A C 0.3075(3) 0.5618(3) 0.19094(15) 0.0314(6) Uani 1 1 d . . .
H12A H 0.4121 0.6079 0.2012 0.038 Uiso 1 1 calc R . .
C12B C 0.7327(3) 0.4634(3) 0.30851(16) 0.0339(6) Uani 1 1 d . . .
H12B H 0.6269 0.4233 0.2944 0.041 Uiso 1 1 calc R . .
C13A C 0.2674(3) 0.5449(3) 0.26599(16) 0.0329(6) Uani 1 1 d . . .
H13A H 0.1640 0.4942 0.2564 0.040 Uiso 1 1 calc R . .
C13B C 0.7849(4) 0.4835(3) 0.23641(18) 0.0400(7) Uani 1 1 d . . .
H13B H 0.8908 0.5218 0.2509 0.048 Uiso 1 1 calc R . .
C14A C 0.3524(4) 0.4851(3) 0.31385(18) 0.0456(8) Uani 1 1 d . . .
H14A H 0.4517 0.5296 0.3316 0.055 Uiso 1 1 calc R . .
C14B C 0.7284(5) 0.5674(4) 0.1933(2) 0.0607(10) Uani 1 1 d U . .
H14B H 0.7561 0.6513 0.2196 0.073 Uiso 1 1 calc R . .
C15A C 0.3009(5) 0.3771(4) 0.3329(2) 0.0702(12) Uani 1 1 d . . .
H15A H 0.2021 0.3298 0.3162 0.084 Uiso 1 1 calc R . .
H15B H 0.3618 0.3451 0.3635 0.084 Uiso 1 1 calc R . .
C15B C 0.6497(5) 0.5423(4) 0.1275(3) 0.0727(12) Uani 1 1 d U . .
H15C H 0.6180 0.4601 0.0980 0.087 Uiso 1 1 calc R . .
H15D H 0.6217 0.6053 0.1070 0.087 Uiso 1 1 calc R . .
C16A C 0.2211(3) 0.6849(3) 0.35803(15) 0.0319(6) Uani 1 1 d . . .
C16B C 0.8234(3) 0.3417(3) 0.14302(16) 0.0334(6) Uani 1 1 d . . .
C17A C 0.2654(3) 0.8181(3) 0.39541(15) 0.0318(6) Uani 1 1 d . . .
C17B C 0.7746(3) 0.2095(3) 0.10342(15) 0.0317(6) Uani 1 1 d . . .
C18A C 0.2009(3) 0.8470(3) 0.45255(16) 0.0369(6) Uani 1 1 d . . .
H18A H 0.1294 0.7822 0.4659 0.044 Uiso 1 1 calc R . .
C18B C 0.8479(3) 0.1789(3) 0.05153(16) 0.0374(6) Uani 1 1 d . . .
H18B H 0.9264 0.2425 0.0424 0.045 Uiso 1 1 calc R . .
C19A C 0.2410(3) 0.9700(3) 0.48983(17) 0.0406(7) Uani 1 1 d . . .
H19A H 0.1982 0.9900 0.5291 0.049 Uiso 1 1 calc R . .
C19B C 0.8075(4) 0.0569(3) 0.01328(18) 0.0430(7) Uani 1 1 d . . .
H19B H 0.8565 0.0361 -0.0226 0.052 Uiso 1 1 calc R . .
C20A C 0.3439(3) 1.0627(3) 0.46888(16) 0.0365(6) Uani 1 1 d . . .
C20B C 0.6939(4) -0.0345(3) 0.02848(18) 0.0465(8) Uani 1 1 d . . .
C21A C 0.4074(3) 1.0368(3) 0.41183(17) 0.0399(7) Uani 1 1 d . . .
H21A H 0.4768 1.1024 0.3977 0.048 Uiso 1 1 calc R . .
C21B C 0.6212(4) -0.0070(3) 0.08035(19) 0.0494(8) Uani 1 1 d . . .
H21B H 0.5444 -0.0714 0.0903 0.059 Uiso 1 1 calc R . .
C22A C 0.3684(3) 0.9137(3) 0.37554(17) 0.0368(6) Uani 1 1 d . . .
H22A H 0.4125 0.8944 0.3367 0.044 Uiso 1 1 calc R . .
C22B C 0.6614(3) 0.1156(3) 0.11774(17) 0.0413(7) Uani 1 1 d . . .
H22B H 0.6116 0.1358 0.1533 0.050 Uiso 1 1 calc R . .
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'
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
_geom_angle_publ_flag
C16A O2A C13A 118.0(2) . . ?
C16B O2B C13B 117.5(2) . . ?
C2A C1A C6A 120.3(3) . . ?
C2A C1A H1AA 119.9 . . ?
C6A C1A H1AA 119.9 . . ?
C2B C1B C6B 120.5(3) . . ?
C2B C1B H1BA 119.8 . . ?
C6B C1B H1BA 119.8 . . ?
C3A C2A C1A 120.4(3) . . ?
C3A C2A H2AA 119.8 . . ?
C1A C2A H2AA 119.8 . . ?
C1B C2B C3B 120.2(3) . . ?
C1B C2B H2BA 119.9 . . ?
C3B C2B H2BA 119.9 . . ?
C2A C3A C4A 119.8(3) . . ?
C2A C3A H3AA 120.1 . . ?
C4A C3A H3AA 120.1 . . ?
C4B C3B C2B 120.0(3) . . ?
C4B C3B H3BA 120.0 . . ?
C2B C3B H3BA 120.0 . . ?
C3A C4A C5A 120.5(4) . . ?
C3A C4A H4AA 119.7 . . ?
C5A C4A H4AA 119.7 . . ?
C3B C4B C5B 120.3(3) . . ?
C3B C4B H4BA 119.8 . . ?
C5B C4B H4BA 119.8 . . ?
C4A C5A C6A 119.8(3) . . ?
C4A C5A H5AA 120.1 . . ?
C6A C5A H5AA 120.1 . . ?
C4B C5B C6B 120.3(3) . . ?
C4B C5B H5BA 119.9 . . ?
C6B C5B H5BA 119.9 . . ?
C1A C6A C5A 119.2(3) . . ?
C1A C6A C7A 118.0(3) . . ?
C5A C6A C7A 122.8(3) . . ?
C5B C6B C1B 118.7(3) . . ?
C5B C6B C7B 123.0(3) . . ?
C1B C6B C7B 118.3(3) . . ?
O1A C7A C6A 120.1(3) . . ?
O1A C7A C8A 119.9(3) . . ?
C6A C7A C8A 120.0(2) . . ?
O1B C7B C6B 120.0(3) . . ?
O1B C7B C8B 120.6(3) . . ?
C6B C7B C8B 119.3(2) . . ?
C7A C8A C12A 113.8(2) . . ?
C7A C8A C9A 110.2(3) . . ?
C12A C8A C9A 104.3(2) . . ?
C7A C8A H8AA 109.5 . . ?
C12A C8A H8AA 109.5 . . ?
C9A C8A H8AA 109.5 . . ?
C7B C8B C12B 113.9(2) . . ?
C7B C8B C9B 109.6(3) . . ?
C12B C8B C9B 104.6(2) . . ?
C7B C8B H8BA 109.5 . . ?
C12B C8B H8BA 109.5 . . ?
C9B C8B H8BA 109.5 . . ?
C10B C9B C8B 106.5(3) . . ?
C10B C9B H9BA 110.4 . . ?
C8B C9B H9BA 110.4 . . ?
C10B C9B H9BB 110.4 . . ?
C8B C9B H9BB 110.4 . . ?
H9BA C9B H9BB 108.6 . . ?
C10A C9A C8A 107.0(3) . . ?
C10A C9A H9AA 110.3 . . ?
C8A C9A H9AA 110.3 . . ?
C10A C9A H9AB 110.3 . . ?
C8A C9A H9AB 110.3 . . ?
H9AA C9A H9AB 108.6 . . ?
C9A C10A C11A 107.9(3) . . ?
C9A C10A H10A 110.1 . . ?
C11A C10A H10A 110.1 . . ?
C9A C10A H10B 110.1 . . ?
C11A C10A H10B 110.1 . . ?
H10A C10A H10B 108.4 . . ?
C9B C10B C11B 107.8(3) . . ?
C9B C10B H10C 110.1 . . ?
C11B C10B H10C 110.1 . . ?
C9B C10B H10D 110.1 . . ?
C11B C10B H10D 110.1 . . ?
H10C C10B H10D 108.5 . . ?
C10A C11A C12A 105.0(2) . . ?
C10A C11A H11A 110.8 . . ?
C12A C11A H11A 110.8 . . ?
C10A C11A H11B 110.8 . . ?
C12A C11A H11B 110.8 . . ?
H11A C11A H11B 108.8 . . ?
C10B C11B C12B 103.3(3) . . ?
C10B C11B H11C 111.1 . . ?
C12B C11B H11C 111.1 . . ?
C10B C11B H11D 111.1 . . ?
C12B C11B H11D 111.1 . . ?
H11C C11B H11D 109.1 . . ?
C13A C12A C8A 113.5(2) . . ?
C13A C12A C11A 112.3(2) . . ?
C8A C12A C11A 103.8(2) . . ?
C13A C12A H12A 109.0 . . ?
C8A C12A H12A 109.0 . . ?
C11A C12A H12A 109.0 . . ?
C13B C12B C11B 113.4(2) . . ?
C13B C12B C8B 112.4(2) . . ?
C11B C12B C8B 103.6(2) . . ?
C13B C12B H12B 109.1 . . ?
C11B C12B H12B 109.1 . . ?
C8B C12B H12B 109.1 . . ?
O2A C13A C14A 108.7(2) . . ?
O2A C13A C12A 105.5(2) . . ?
C14A C13A C12A 112.9(2) . . ?
O2A C13A H13A 109.9 . . ?
C14A C13A H13A 109.9 . . ?
C12A C13A H13A 109.9 . . ?
O2B C13B C14B 112.1(3) . . ?
O2B C13B C12B 105.6(2) . . ?
C14B C13B C12B 113.4(3) . . ?
O2B C13B H13B 108.5 . . ?
C14B C13B H13B 108.5 . . ?
C12B C13B H13B 108.5 . . ?
C15A C14A C13A 124.8(4) . . ?
C15A C14A H14A 117.6 . . ?
C13A C14A H14A 117.6 . . ?
C15B C14B C13B 128.9(4) . . ?
C15B C14B H14B 115.5 . . ?
C13B C14B H14B 115.5 . . ?
C14A C15A H15A 120.0 . . ?
C14A C15A H15B 120.0 . . ?
H15A C15A H15B 120.0 . . ?
C14B C15B H15C 120.0 . . ?
C14B C15B H15D 120.0 . . ?
H15C C15B H15D 120.0 . . ?
O3A C16A O2A 123.7(3) . . ?
O3A C16A C17A 124.9(3) . . ?
O2A C16A C17A 111.5(2) . . ?
O3B C16B O2B 123.5(3) . . ?
O3B C16B C17B 124.4(3) . . ?
O2B C16B C17B 112.1(2) . . ?
C22A C17A C18A 119.4(3) . . ?
C22A C17A C16A 122.1(2) . . ?
C18A C17A C16A 118.4(3) . . ?
C22B C17B C18B 119.5(3) . . ?
C22B C17B C16B 122.3(3) . . ?
C18B C17B C16B 118.2(3) . . ?
C19A C18A C17A 120.3(3) . . ?
C19A C18A H18A 119.9 . . ?
C17A C18A H18A 119.9 . . ?
C19B C18B C17B 120.6(3) . . ?
C19B C18B H18B 119.7 . . ?
C17B C18B H18B 119.7 . . ?
C20A C19A C18A 118.9(3) . . ?
C20A C19A H19A 120.6 . . ?
C18A C19A H19A 120.6 . . ?
C18B C19B C20B 118.5(3) . . ?
C18B C19B H19B 120.8 . . ?
C20B C19B H19B 120.8 . . ?
C19A C20A C21A 122.0(3) . . ?
C19A C20A Br1A 118.9(2) . . ?
C21A C20A Br1A 119.1(2) . . ?
C21B C20B C19B 122.0(3) . . ?
C21B C20B Br1B 119.4(3) . . ?
C19B C20B Br1B 118.6(2) . . ?
C20A C21A C22A 118.9(3) . . ?
C20A C21A H21A 120.5 . . ?
C22A C21A H21A 120.5 . . ?
C20B C21B C22B 119.1(3) . . ?
C20B C21B H21B 120.4 . . ?
C22B C21B H21B 120.4 . . ?
C21A C22A C17A 120.5(3) . . ?
C21A C22A H22A 119.7 . . ?
C17A C22A H22A 119.7 . . ?
C21B C22B C17B 120.2(3) . . ?
C21B C22B H22B 119.9 . . ?
C17B C22B H22B 119.9 . . ?
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
Br1A C20A 1.898(3) . ?
Br1B C20B 1.896(3) . ?
O1A C7A 1.219(3) . ?
O1B C7B 1.218(3) . ?
O2A C16A 1.348(3) . ?
O2A C13A 1.461(3) . ?
O2B C16B 1.343(3) . ?
O2B C13B 1.459(3) . ?
O3A C16A 1.208(3) . ?
O3B C16B 1.207(4) . ?
C1A C2A 1.386(5) . ?
C1A C6A 1.396(4) . ?
C1A H1AA 0.9500 . ?
C1B C2B 1.378(4) . ?
C1B C6B 1.399(4) . ?
C1B H1BA 0.9500 . ?
C2A C3A 1.380(6) . ?
C2A H2AA 0.9500 . ?
C2B C3B 1.382(5) . ?
C2B H2BA 0.9500 . ?
C3A C4A 1.380(6) . ?
C3A H3AA 0.9500 . ?
C3B C4B 1.373(5) . ?
C3B H3BA 0.9500 . ?
C4A C5A 1.394(5) . ?
C4A H4AA 0.9500 . ?
C4B C5B 1.388(4) . ?
C4B H4BA 0.9500 . ?
C5A C6A 1.396(4) . ?
C5A H5AA 0.9500 . ?
C5B C6B 1.389(4) . ?
C5B H5BA 0.9500 . ?
C6A C7A 1.494(4) . ?
C6B C7B 1.501(4) . ?
C7A C8A 1.515(4) . ?
C7B C8B 1.513(4) . ?
C8A C12A 1.531(4) . ?
C8A C9A 1.537(5) . ?
C8A H8AA 1.0000 . ?
C8B C12B 1.536(4) . ?
C8B C9B 1.555(4) . ?
C8B H8BA 1.0000 . ?
C9B C10B 1.498(5) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9A C10A 1.499(5) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A C11A 1.520(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10B C11B 1.522(5) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11A C12A 1.541(4) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11B C12B 1.536(4) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12A C13A 1.509(4) . ?
C12A H12A 1.0000 . ?
C12B C13B 1.517(4) . ?
C12B H12B 1.0000 . ?
C13A C14A 1.495(4) . ?
C13A H13A 1.0000 . ?
C13B C14B 1.498(5) . ?
C13B H13B 1.0000 . ?
C14A C15A 1.293(5) . ?
C14A H14A 0.9500 . ?
C14B C15B 1.251(6) . ?
C14B H14B 0.9500 . ?
C15A H15A 0.9500 . ?
C15A H15B 0.9500 . ?
C15B H15C 0.9500 . ?
C15B H15D 0.9500 . ?
C16A C17A 1.485(4) . ?
C16B C17B 1.481(4) . ?
C17A C22A 1.388(4) . ?
C17A C18A 1.397(4) . ?
C17B C22B 1.392(4) . ?
C17B C18B 1.395(4) . ?
C18A C19A 1.387(4) . ?
C18A H18A 0.9500 . ?
C18B C19B 1.382(4) . ?
C18B H18B 0.9500 . ?
C19A C20A 1.378(5) . ?
C19A H19A 0.9500 . ?
C19B C20B 1.387(5) . ?
C19B H19B 0.9500 . ?
C20A C21A 1.379(4) . ?
C20B C21B 1.378(5) . ?
C21A C22A 1.384(4) . ?
C21A H21A 0.9500 . ?
C21B C22B 1.384(4) . ?
C21B H21B 0.9500 . ?
C22A H22A 0.9500 . ?
C22B H22B 0.9500 . ?
