#------------------------------------------------------------------------------
#$Date: 2023-10-16 10:18:21 +0300 (Mon, 16 Oct 2023) $
#$Revision: 286979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107626.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_8107626
loop_
_publ_author_name
'Wang, Hua-Bin'
'Xu, Lian-Hua'
'Shi, Ju-Mei'
'Zhou, Ying'
'Hao, Yong-Jia'
_publ_section_title
;
 Crystal structure of
 (Z)-2-(4-((5-bromopentyl)oxy)benzylidene)-4,5,6-trimethoxybenzofuran-3(2H)-one,
 C23H25BrO6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1013
_journal_page_last               1015
_journal_paper_doi               10.1515/ncrs-2023-0329
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C23 H25 Br O6'
_chemical_formula_sum            'C23 H25 Br O6'
_chemical_formula_weight         477.34
_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   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.146(3)
_cell_angle_beta                 90.433(3)
_cell_angle_gamma                99.307(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8451(3)
_cell_length_b                   7.9428(2)
_cell_length_c                   17.6360(6)
_cell_measurement_reflns_used    9760
_cell_measurement_temperature    297.37(10)
_cell_measurement_theta_max      76.7620
_cell_measurement_theta_min      2.5060
_cell_volume                     1084.43(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.37(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -51.00 -26.00   0.50    0.40    --  -91.75  45.00-150.00   50
  2  ω    -47.00 -19.00   0.50    0.40    --  -91.75  52.00-122.00   56
  3  ω    -51.00 -24.00   0.50    0.40    --  -91.75  45.00 -60.00   54
  4  ω    -48.00 -22.00   0.50    0.40    --  -91.75  45.00  90.00   52
  5  ω    -27.00  16.00   0.50    0.14    --  -47.50  19.00 120.00   86
  6  ω   -105.00 -70.00   0.50    0.14    --  -47.50-125.00 -60.00   70
  7  ω   -164.00-138.00   0.50    0.40    --  -91.75 -52.00  92.00   52
  8  ω   -135.00 -77.00   0.50    0.40    --  -91.75 -52.00  92.00  116
  9  ω    -98.00 -73.00   0.50    0.14    --  -47.50-125.00 120.00   50
 10  ω   -163.00-106.00   0.50    0.40    --  -91.75 -87.00-126.00  114
 11  ω    -16.00  26.00   0.50    0.14    --   47.50 -19.00 -90.00   84
 12  ω     46.00  71.00   0.50    0.40    --  108.56 -61.00-120.00   50
 13  ω     43.00  70.00   0.50    0.40    --  108.56 -61.00 -90.00   54
 14  ω     42.00  70.00   0.50    0.40    --  108.56 -86.00 -22.00   56
 15  ω     99.00 136.00   0.50    0.40    --  108.56 -86.00 -22.00   74
 16  ω    -14.00  22.00   0.50    0.14    --   47.50 -86.00 -23.00   72
 17  ω   -106.00 -80.00   0.50    0.14    --  -47.50-125.00  30.00   52
 18  ω   -123.00 -34.00   0.50    0.14    --  -47.50 -19.00 -30.00  178
 19  ω    -61.00  18.00   0.50    0.14    --  -47.50  57.00 150.00  158
 20  ω     28.00  74.00   0.50    0.14    --   47.50 -86.00 -23.00   92
 21  ω     34.00  91.00   0.50    0.14    --   47.50-125.00-120.00  114
 22  ω    -51.00 -19.00   0.50    0.40    --  -91.75  45.00 -90.00   64
 23  ω   -118.00 -87.00   0.50    0.40    --  -91.75 -30.00   0.00   62
 24  ω   -158.00-128.00   0.50    0.40    --  -91.75 -30.00   0.00   60
 25  ω   -138.00 -84.00   0.50    0.40    --  -91.75 -15.00 -60.00  108
 26  ω   -161.00-121.00   0.50    0.40    --  -91.75-125.00  90.00   80
 27  ω   -165.00-124.00   0.50    0.40    --  -91.75 -30.00-120.00   82
 28  ω    -74.00 -27.00   0.50    0.40    --  -91.75 125.00-120.00   94
 29  ω   -117.00 -91.00   0.50    0.40    --  -91.75-125.00  90.00   52
 30  ω   -145.00 -71.00   0.50    0.40    --  -91.75-125.00   0.00  148
 31  ω     41.00  78.00   0.50    0.40    --  108.56-125.00-150.00   74
 32  ω     95.00 120.00   0.50    0.40    --  108.56 125.00-120.00   50
 33  ω     41.00  67.00   0.50    0.40    --  108.56 -61.00 150.00   52
 34  ω     59.00 106.00   0.50    0.40    --  108.56-125.00  30.00   94
 35  ω     89.00 115.00   0.50    0.40    --  108.56-125.00  90.00   52
 36  ω     68.00  95.00   0.50    0.40    --  108.56-125.00   0.00   54
 37  ω     80.00 112.00   0.50    0.40    --  108.56-125.00 -90.00   64
 38  ω     37.00  69.00   0.50    0.40    --  108.56 -94.00  90.00   64
 39  ω     79.00 106.00   0.50    0.40    --  108.56 -94.00  90.00   54
 40  ω     96.00 174.00   0.50    0.40    --  108.56  45.00-120.00  156
 41  ω     43.00  70.00   0.50    0.40    --  108.56-125.00  90.00   54
 42  ω     38.00 108.00   0.50    0.40    --  108.56 -94.00-120.00  140
 43  ω     42.00  74.00   0.50    0.40    --  108.56 -94.00 -30.00   64
 44  ω     68.00 123.00   0.50    0.40    --  108.56-133.00  73.37  110
 45  ω    150.00 178.00   0.50    0.40    --  108.56 125.00-120.00   56
 46  ω     83.00 116.00   0.50    0.40    --  108.56-125.00-150.00   66
 47  ω     36.00  62.00   0.50    0.40    --  108.56 -61.00   0.00   52
 48  ω     99.00 172.00   0.50    0.40    --  108.56 125.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1358070000
_diffrn_orient_matrix_UB_12      -0.0477052000
_diffrn_orient_matrix_UB_13      -0.0632781000
_diffrn_orient_matrix_UB_21      0.1315823000
_diffrn_orient_matrix_UB_22      -0.0822051000
_diffrn_orient_matrix_UB_23      -0.0458275000
_diffrn_orient_matrix_UB_31      -0.0619882000
_diffrn_orient_matrix_UB_32      -0.1720328000
_diffrn_orient_matrix_UB_33      0.0390756000
_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  0.0682
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.353
_diffrn_reflns_theta_min         2.505
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0047(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0464
_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)+(0.0802P)²+0.2106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3720
_reflns_number_total             4301
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0329_suppl_001.cif
_cod_data_source_block           6275
_cod_original_cell_volume        1084.44(7)
_cod_database_code               8107626
_chemical_oxdiff_formula         'C H N O Br'
_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   0.781
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 1.650
_oxdiff_exptl_absorpt_empirical_full_min 0.457
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 1.27441(4) 1.03425(4) 0.27130(2) 0.07969(18) Uani 1 1 d . . . . .
O1 O -0.5527(2) 0.2611(2) 0.92297(10) 0.0592(4) Uani 1 1 d . . . . .
O2 O -0.3932(2) 0.1774(2) 1.05043(9) 0.0608(4) Uani 1 1 d . . . . .
O3 O -0.0506(2) 0.2060(3) 1.05879(10) 0.0647(5) Uani 1 1 d . . . . .
O4 O -0.0102(2) 0.4337(2) 0.80501(8) 0.0519(4) Uani 1 1 d . . . . .
O5 O -0.4464(2) 0.4387(3) 0.75866(12) 0.0702(5) Uani 1 1 d . . . . .
O6 O 0.5160(3) 0.7301(3) 0.52979(10) 0.0689(5) Uani 1 1 d . . . . .
C1 C -0.0968(3) 0.3652(3) 0.86886(12) 0.0474(5) Uani 1 1 d . . . . .
C2 C -0.2751(3) 0.3481(3) 0.86180(12) 0.0471(5) Uani 1 1 d . . . . .
C3 C -0.3779(3) 0.2831(3) 0.92368(13) 0.0483(5) Uani 1 1 d . . . . .
C4 C -0.2960(3) 0.2429(3) 0.98960(13) 0.0509(5) Uani 1 1 d . . . . .
C5 C -0.1142(3) 0.2589(3) 0.99307(13) 0.0507(5) Uani 1 1 d . . . . .
C6 C -0.0102(3) 0.3218(3) 0.93210(12) 0.0507(5) Uani 1 1 d . . . . .
H6 H 0.112223 0.333828 0.934228 0.061 Uiso 1 1 calc R U . . .
C7 C -0.3098(3) 0.4184(3) 0.78802(13) 0.0520(5) Uani 1 1 d . . . . .
C8 C -0.1365(3) 0.4690(3) 0.75421(13) 0.0496(5) Uani 1 1 d . . . . .
C9 C -0.1045(3) 0.5373(3) 0.68580(13) 0.0511(5) Uani 1 1 d . . . . .
H9 H -0.204283 0.554741 0.657994 0.061 Uiso 1 1 calc R U . . .
C10 C 0.0579(3) 0.5897(3) 0.64666(12) 0.0469(5) Uani 1 1 d . . . . .
C11 C 0.2201(3) 0.5822(3) 0.67850(12) 0.0512(5) Uani 1 1 d . . . . .
H11 H 0.227786 0.542114 0.728913 0.061 Uiso 1 1 calc R U . . .
C12 C 0.3686(3) 0.6319(3) 0.63819(13) 0.0544(5) Uani 1 1 d . . . . .
H12 H 0.477619 0.627938 0.661358 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3612(3) 0.6881(3) 0.56357(13) 0.0518(5) Uani 1 1 d . . . . .
C14 C 0.2019(3) 0.6975(3) 0.53078(13) 0.0556(5) Uani 1 1 d . . . . .
H14 H 0.194836 0.736961 0.480220 0.067 Uiso 1 1 calc R U . . .
C15 C 0.0530(3) 0.6488(3) 0.57237(13) 0.0539(5) Uani 1 1 d . . . . .
H15 H -0.055761 0.655973 0.549613 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5260(4) 0.7836(4) 0.45233(14) 0.0607(6) Uani 1 1 d . . . . .
H16A H 0.474245 0.888259 0.445468 0.073 Uiso 1 1 calc R U . . .
H16B H 0.465214 0.692991 0.418677 0.073 Uiso 1 1 calc R U . . .
C17 C 0.7162(4) 0.8174(3) 0.43548(14) 0.0601(6) Uani 1 1 d . . . . .
H17A H 0.763082 0.709899 0.442426 0.072 Uiso 1 1 calc R U . . .
H17B H 0.774063 0.900676 0.473109 0.072 Uiso 1 1 calc R U . . .
C18 C 0.7629(4) 0.8852(3) 0.35637(14) 0.0601(6) Uani 1 1 d . . . . .
H18A H 0.718303 0.993521 0.348261 0.072 Uiso 1 1 calc R U . . .
H18B H 0.710146 0.801822 0.317695 0.072 Uiso 1 1 calc R U . . .
C19 C 0.9600(4) 0.9151(4) 0.34884(15) 0.0630(6) Uani 1 1 d . . . . .
H19A H 1.011316 0.993899 0.389522 0.076 Uiso 1 1 calc R U . . .
H19B H 1.002512 0.805413 0.355846 0.076 Uiso 1 1 calc R U . . .
C20 C 1.0191(4) 0.9887(4) 0.27333(16) 0.0656(6) Uani 1 1 d . . . . .
H20A H 0.973057 1.096085 0.264740 0.079 Uiso 1 1 calc R U . . .
H20B H 0.974839 0.907453 0.232375 0.079 Uiso 1 1 calc R U . . .
C21 C -0.6376(3) 0.1674(4) 0.85969(15) 0.0622(6) Uani 1 1 d . . . . .
H21A H -0.680648 0.246570 0.824588 0.093 Uiso 1 1 calc R U . . .
H21B H -0.734585 0.084337 0.877951 0.093 Uiso 1 1 calc R U . . .
H21C H -0.555395 0.107424 0.833404 0.093 Uiso 1 1 calc R U . . .
C22 C -0.4035(5) 0.2988(4) 1.10891(17) 0.0761(8) Uani 1 1 d . . . . .
H22A H -0.458260 0.392111 1.088902 0.114 Uiso 1 1 calc R U . . .
H22B H -0.287062 0.344351 1.127402 0.114 Uiso 1 1 calc R U . . .
H22C H -0.472487 0.243507 1.150747 0.114 Uiso 1 1 calc R U . . .
C23 C 0.1317(4) 0.2066(4) 1.06402(16) 0.0705(7) Uani 1 1 d . . . . .
H23A H 0.166512 0.132123 1.024634 0.106 Uiso 1 1 calc R U . . .
H23B H 0.160335 0.165076 1.114055 0.106 Uiso 1 1 calc R U . . .
H23C H 0.192991 0.323097 1.056965 0.106 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'
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
C3 O1 C21 116.26(18) . .
C4 O2 C22 113.6(2) . .
C5 O3 C23 117.8(2) . .
C1 O4 C8 106.31(17) . .
C13 O6 C16 120.4(2) . .
O4 C1 C2 113.21(18) . .
C6 C1 O4 121.8(2) . .
C6 C1 C2 124.9(2) . .
C1 C2 C3 118.64(19) . .
C1 C2 C7 106.43(19) . .
C3 C2 C7 134.8(2) . .
O1 C3 C2 123.6(2) . .
O1 C3 C4 117.9(2) . .
C4 C3 C2 118.5(2) . .
O2 C4 C3 119.6(2) . .
O2 C4 C5 119.7(2) . .
C3 C4 C5 120.5(2) . .
O3 C5 C4 114.9(2) . .
O3 C5 C6 123.3(2) . .
C6 C5 C4 121.8(2) . .
C1 C6 C5 115.6(2) . .
C1 C6 H6 122.2 . .
C5 C6 H6 122.2 . .
O5 C7 C2 130.2(2) . .
O5 C7 C8 125.3(2) . .
C2 C7 C8 104.44(19) . .
O4 C8 C7 109.54(18) . .
C9 C8 O4 124.6(2) . .
C9 C8 C7 125.9(2) . .
C8 C9 H9 114.6 . .
C8 C9 C10 130.7(2) . .
C10 C9 H9 114.6 . .
C11 C10 C9 123.99(19) . .
C15 C10 C9 118.6(2) . .
C15 C10 C11 117.4(2) . .
C10 C11 H11 119.4 . .
C12 C11 C10 121.1(2) . .
C12 C11 H11 119.4 . .
C11 C12 H12 119.7 . .
C11 C12 C13 120.7(2) . .
C13 C12 H12 119.7 . .
O6 C13 C12 114.8(2) . .
O6 C13 C14 125.8(2) . .
C14 C13 C12 119.3(2) . .
C13 C14 H14 120.3 . .
C15 C14 C13 119.4(2) . .
C15 C14 H14 120.3 . .
C10 C15 H15 119.0 . .
C14 C15 C10 122.0(2) . .
C14 C15 H15 119.0 . .
O6 C16 H16A 110.8 . .
O6 C16 H16B 110.8 . .
O6 C16 C17 104.7(2) . .
H16A C16 H16B 108.9 . .
C17 C16 H16A 110.8 . .
C17 C16 H16B 110.8 . .
C16 C17 H17A 108.5 . .
C16 C17 H17B 108.5 . .
C16 C17 C18 115.3(2) . .
H17A C17 H17B 107.5 . .
C18 C17 H17A 108.5 . .
C18 C17 H17B 108.5 . .
C17 C18 H18A 109.9 . .
C17 C18 H18B 109.9 . .
C17 C18 C19 108.7(2) . .
H18A C18 H18B 108.3 . .
C19 C18 H18A 109.9 . .
C19 C18 H18B 109.9 . .
C18 C19 H19A 109.1 . .
C18 C19 H19B 109.1 . .
H19A C19 H19B 107.8 . .
C20 C19 C18 112.6(2) . .
C20 C19 H19A 109.1 . .
C20 C19 H19B 109.1 . .
Br1 C20 H20A 109.8 . .
Br1 C20 H20B 109.8 . .
C19 C20 Br1 109.5(2) . .
C19 C20 H20A 109.8 . .
C19 C20 H20B 109.8 . .
H20A C20 H20B 108.2 . .
O1 C21 H21A 109.5 . .
O1 C21 H21B 109.5 . .
O1 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O2 C22 H22A 109.5 . .
O2 C22 H22B 109.5 . .
O2 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
O3 C23 H23A 109.5 . .
O3 C23 H23B 109.5 . .
O3 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C20 1.978(3) .
O1 C3 1.354(3) .
O1 C21 1.438(3) .
O2 C4 1.375(3) .
O2 C22 1.422(4) .
O3 C5 1.353(3) .
O3 C23 1.431(3) .
O4 C1 1.386(3) .
O4 C8 1.393(3) .
O5 C7 1.220(3) .
O6 C13 1.350(3) .
O6 C16 1.431(3) .
C1 C2 1.388(3) .
C1 C6 1.375(3) .
C2 C3 1.410(3) .
C2 C7 1.458(3) .
C3 C4 1.386(3) .
C4 C5 1.412(3) .
C5 C6 1.399(3) .
C6 H6 0.9500 .
C7 C8 1.484(3) .
C8 C9 1.333(3) .
C9 H9 0.9500 .
C9 C10 1.454(3) .
C10 C11 1.397(3) .
C10 C15 1.395(3) .
C11 H11 0.9500 .
C11 C12 1.372(3) .
C12 H12 0.9500 .
C12 C13 1.395(3) .
C13 C14 1.386(3) .
C14 H14 0.9500 .
C14 C15 1.386(4) .
C15 H15 0.9500 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.505(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.523(3) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C19 1.533(4) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.502(4) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 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
O1 C3 C4 O2 2.2(3) . . . .
O1 C3 C4 C5 178.3(2) . . . .
O2 C4 C5 O3 -0.1(3) . . . .
O2 C4 C5 C6 178.8(2) . . . .
O3 C5 C6 C1 178.2(2) . . . .
O4 C1 C2 C3 -178.72(19) . . . .
O4 C1 C2 C7 -2.7(3) . . . .
O4 C1 C6 C5 178.2(2) . . . .
O4 C8 C9 C10 0.6(4) . . . .
O5 C7 C8 O4 177.2(2) . . . .
O5 C7 C8 C9 -2.9(4) . . . .
O6 C13 C14 C15 179.6(2) . . . .
O6 C16 C17 C18 -177.2(2) . . . .
C1 O4 C8 C7 -0.5(2) . . . .
C1 O4 C8 C9 179.6(2) . . . .
C1 C2 C3 O1 -180.0(2) . . . .
C1 C2 C3 C4 1.5(3) . . . .
C1 C2 C7 O5 -176.0(3) . . . .
C1 C2 C7 C8 2.1(2) . . . .
C2 C1 C6 C5 -1.1(3) . . . .
C2 C3 C4 O2 -179.2(2) . . . .
C2 C3 C4 C5 -3.2(3) . . . .
C2 C7 C8 O4 -1.0(2) . . . .
C2 C7 C8 C9 178.8(2) . . . .
C3 C2 C7 O5 -0.9(5) . . . .
C3 C2 C7 C8 177.2(2) . . . .
C3 C4 C5 O3 -176.1(2) . . . .
C3 C4 C5 C6 2.7(4) . . . .
C4 C5 C6 C1 -0.6(3) . . . .
C6 C1 C2 C3 0.6(3) . . . .
C6 C1 C2 C7 176.7(2) . . . .
C7 C2 C3 O1 5.4(4) . . . .
C7 C2 C3 C4 -173.1(2) . . . .
C7 C8 C9 C10 -179.2(2) . . . .
C8 O4 C1 C2 2.0(2) . . . .
C8 O4 C1 C6 -177.3(2) . . . .
C8 C9 C10 C11 -2.9(4) . . . .
C8 C9 C10 C15 176.1(3) . . . .
C9 C10 C11 C12 179.3(2) . . . .
C9 C10 C15 C14 -178.6(2) . . . .
C10 C11 C12 C13 -1.3(4) . . . .
C11 C10 C15 C14 0.5(4) . . . .
C11 C12 C13 O6 -178.8(2) . . . .
C11 C12 C13 C14 1.6(4) . . . .
C12 C13 C14 C15 -0.8(4) . . . .
C13 O6 C16 C17 -179.7(2) . . . .
C13 C14 C15 C10 -0.2(4) . . . .
C15 C10 C11 C12 0.2(3) . . . .
C16 O6 C13 C12 177.7(2) . . . .
C16 O6 C13 C14 -2.7(4) . . . .
C16 C17 C18 C19 179.2(2) . . . .
C17 C18 C19 C20 -177.8(2) . . . .
C18 C19 C20 Br1 176.92(18) . . . .
C21 O1 C3 C2 51.3(3) . . . .
C21 O1 C3 C4 -130.2(2) . . . .
C22 O2 C4 C3 -102.4(3) . . . .
C22 O2 C4 C5 81.5(3) . . . .
C23 O3 C5 C4 175.4(2) . . . .
C23 O3 C5 C6 -3.4(4) . . . .
