#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:11:07 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571949.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_1571949
loop_
_publ_author_name
'Arnold, Robert E.'
'Saska, Jan'
'Mesquita-Ribeiro, Raquel'
'Dajas-Bailador, Federico'
'Taylor, Laurence'
'Lewis, William'
'Argent, Stephen'
'Shao, Huiling'
'Houk, Kendall N.'
'Denton, Ross M.'
_publ_section_title
;
 Total synthesis, biological evaluation and biosynthetic re-evaluation of
 Illicium-derived neolignans.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              11783
_journal_page_last               11793
_journal_paper_doi               10.1039/d4sc03232b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C19 H19 Br O3'
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_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     iterative
_audit_creation_date             2018-02-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.265(4)
_cell_angle_beta                 105.787(4)
_cell_angle_gamma                106.880(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0674(3)
_cell_length_b                   10.0413(5)
_cell_length_c                   11.4509(5)
_cell_measurement_reflns_used    10446
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4480
_cell_measurement_theta_min      4.0290
_cell_volume                     850.63(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  34.00   1.00    2.50    --  -38.50  38.00 -60.00   84
  2  ω   -109.00 -12.00   1.00    2.50    --  -38.50 -57.00   0.00   97
  3  ω    -65.00  32.00   1.00    2.50    --  -38.50  57.00 150.00   97
  4  ω      1.00  83.00   1.00    2.50    --   43.32 -99.00-150.00   82
  5  ω      1.00  83.00   1.00    2.50    --   43.32 -99.00-120.00   82
  6  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00 -60.00   63
  7  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00-120.00   60
  8  ω     32.00 138.00   1.00   10.00    --  106.13 -77.00 120.00  106
  9  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00  90.00   60
 10  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00  60.00   84
 11  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00-120.00   84
 12  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00-150.00   63
 13  ω     35.00 121.00   1.00   10.00    --  106.13-125.00 -60.00   86
 14  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00 120.00   60
 15  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00  30.00   63
 16  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00  60.00   60
 17  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00 -30.00   84
 18  ω     19.00 178.00   1.00   10.00    --  106.13   0.00 -90.00  159
 19  ω    -50.00  34.00   1.00    2.50    --  -38.50  38.00  60.00   84
 20  ω     17.00 113.00   1.00    2.50    --   43.32  57.00 -90.00   96
 21  ω     12.00 117.00   1.00    2.50    --   43.32  77.00 150.00  105
 22  ω     17.00 113.00   1.00    2.50    --   43.32  57.00  60.00   96
 23  ω     12.00 117.00   1.00    2.50    --   43.32  77.00 -60.00  105
 24  ω     82.00 178.00   1.00   10.00    --  106.13  30.00 -30.00   96
 25  ω     75.00 178.00   1.00   10.00    --  106.13  77.00 150.00  103
 26  ω     61.00 178.00   1.00   10.00    --  106.13  15.00  90.00  117
 27  ω     82.00 177.00   1.00   10.00    --  106.13  45.00 -90.00   95
 28  ω     79.00 176.00   1.00   10.00    --  106.13  61.00-150.00   97
 29  ω     79.00 176.00   1.00   10.00    --  106.13  61.00   0.00   97
 30  ω     75.00 178.00   1.00   10.00    --  106.13  77.00  60.00  103
 31  ω     79.00 176.00   1.00   10.00    --  106.13  61.00 -30.00   97
 32  ω     75.00 178.00   1.00   10.00    --  106.13  77.00-180.00  103
 33  ω     79.00 176.00   1.00   10.00    --  106.13  61.00 120.00   97
 34  ω     12.00  67.00   1.00    2.50    --   43.32  77.00  90.00   55
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1419749000
_diffrn_orient_matrix_UB_12      0.1015917000
_diffrn_orient_matrix_UB_13      -0.0504568000
_diffrn_orient_matrix_UB_21      0.1122728000
_diffrn_orient_matrix_UB_22      -0.1028947000
_diffrn_orient_matrix_UB_23      0.0193747000
_diffrn_orient_matrix_UB_31      -0.1029666000
_diffrn_orient_matrix_UB_32      -0.0707896000
_diffrn_orient_matrix_UB_33      -0.1295689000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_min         4.029
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    3.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0234
_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)+(0.0326P)²+0.5214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3321
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03232b2.cif
_cod_data_source_block           30
_cod_depositor_comments
'Adding full bibliography for 1571943--1571950.cif.'
_cod_database_code               1571949
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C19 H19 Br O3'
_chemical_oxdiff_usercomment
'REARDG #17455 SN-1272 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
_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   0.911
_shelx_estimated_absorpt_t_min   0.350
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2018-02-20
_olex2_date_sample_submission    2018-01-16
_olex2_submission_original_sample_id RA-320-001
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.710
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
O1 O 0.64606(14) 0.71997(12) 0.32510(11) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.7119(2) 0.61153(16) 0.38244(15) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.622112 0.555360 0.422530 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8897(2) 0.67307(16) 0.47845(15) 0.0189(3) Uani 1 1 d . . . . .
H3A H 0.931040 0.596371 0.518083 0.023 Uiso 1 1 calc R . . . .
H3B H 0.872002 0.730773 0.541622 0.023 Uiso 1 1 calc R . . . .
C4 C 1.0385(2) 0.76477(16) 0.42527(14) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.9543(2) 0.85029(16) 0.32955(14) 0.0168(3) Uani 1 1 d . . . . .
C6 C 1.0657(2) 0.95881(17) 0.28476(15) 0.0197(3) Uani 1 1 d . . . . .
H6 H 1.192995 0.978380 0.315012 0.024 Uiso 1 1 calc R . . . .
C7 C 0.9964(2) 1.03933(17) 0.19724(15) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.8092(2) 1.01193(17) 0.15601(15) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.758331 1.066725 0.097681 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6978(2) 0.90465(17) 0.20041(14) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.7670(2) 0.82186(16) 0.28591(14) 0.0168(3) Uani 1 1 d . . . . .
O11 O 0.73141(15) 0.52315(12) 0.29600(11) 0.0221(2) Uani 1 1 d . . . . .
C12 C 0.5641(2) 0.45698(19) 0.20373(17) 0.0276(4) Uani 1 1 d . . . . .
H12A H 0.525105 0.527406 0.152114 0.033 Uiso 1 1 calc R . . . .
H12B H 0.468336 0.411958 0.242267 0.033 Uiso 1 1 calc R . . . .
C13 C 0.5946(3) 0.3497(2) 0.1277(2) 0.0391(5) Uani 1 1 d . . . . .
H13A H 0.482816 0.304494 0.063292 0.059 Uiso 1 1 calc GR . . . .
H13B H 0.630358 0.279257 0.179192 0.059 Uiso 1 1 calc GR . . . .
H13C H 0.690641 0.394994 0.090840 0.059 Uiso 1 1 calc GR . . . .
C14 C 1.1785(2) 0.86060(17) 0.52979(15) 0.0202(3) Uani 1 1 d . . . . .
H14 H 1.145207 0.930105 0.566371 0.024 Uiso 1 1 calc R . . . .
C15 C 1.3464(2) 0.85430(18) 0.57440(15) 0.0228(3) Uani 1 1 d . . . . .
H15 H 1.427142 0.918324 0.641106 0.027 Uiso 1 1 calc R . . . .
C16 C 1.4099(2) 0.75070(18) 0.52293(15) 0.0221(3) Uani 1 1 d . . . . .
C17 C 1.2860(2) 0.66766(17) 0.41058(15) 0.0208(3) Uani 1 1 d . . . . .
H17 H 1.326847 0.607698 0.368502 0.025 Uiso 1 1 calc R . . . .
C18 C 1.1181(2) 0.67385(16) 0.36589(14) 0.0177(3) Uani 1 1 d . . . . .
H18 H 1.044315 0.618023 0.292629 0.021 Uiso 1 1 calc R . . . .
O19 O 1.55674(17) 0.73393(16) 0.57195(12) 0.0319(3) Uani 1 1 d . . . . .
C20 C 1.1241(2) 1.15015(19) 0.14643(17) 0.0271(4) Uani 1 1 d . . . . .
H20A H 1.239208 1.189244 0.211469 0.033 Uiso 1 1 calc R . . . .
H20B H 1.151055 1.104854 0.079828 0.033 Uiso 1 1 calc R . . . .
C21 C 1.0547(3) 1.26745(19) 0.09871(18) 0.0305(4) Uani 1 1 d . . . . .
H21 H 1.020261 1.318853 0.152868 0.037 Uiso 1 1 calc R . . . .
C22 C 1.0376(3) 1.3051(2) -0.0126(2) 0.0384(5) Uani 1 1 d . . . . .
H22A H 1.070700 1.256232 -0.069412 0.046 Uiso 1 1 calc R . . . .
H22B H 0.992216 1.381228 -0.036317 0.046 Uiso 1 1 calc R . . . .
Br23 Br 0.44335(2) 0.86941(2) 0.14596(2) 0.02289(7) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0010
0 -1 0 0.0270
0 -1 1 0.0151
0 1 -1 0.0140
4 -2 -5 0.1443
-5 1 1 0.1969
0 -2 -6 0.0396
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
C10 O1 C2 115.91(11) . . ?
O1 C2 H2 108.5 . . ?
O1 C2 C3 110.57(13) . . ?
C3 C2 H2 108.5 . . ?
O11 C2 O1 110.47(13) . . ?
O11 C2 H2 108.5 . . ?
O11 C2 C3 110.11(13) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.53(13) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C5 C4 C3 109.07(12) . . ?
C14 C4 C3 106.66(13) . . ?
C14 C4 C5 110.01(12) . . ?
C14 C4 C18 111.68(13) . . ?
C18 C4 C3 110.41(12) . . ?
C18 C4 C5 108.97(12) . . ?
C6 C5 C4 119.74(13) . . ?
C6 C5 C10 119.08(14) . . ?
C10 C5 C4 121.18(13) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.16(15) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 118.32(14) . . ?
C6 C7 C20 119.67(15) . . ?
C8 C7 C20 121.98(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.79(15) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 121.88(14) . . ?
C8 C9 Br23 119.70(12) . . ?
C10 C9 Br23 118.42(12) . . ?
O1 C10 C5 123.86(14) . . ?
O1 C10 C9 117.35(13) . . ?
C9 C10 C5 118.74(14) . . ?
C2 O11 C12 112.81(12) . . ?
O11 C12 H12A 110.1 . . ?
O11 C12 H12B 110.1 . . ?
O11 C12 C13 108.13(15) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14 117.9 . . ?
C15 C14 C4 124.16(15) . . ?
C15 C14 H14 117.9 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.59(16) . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 116.02(14) . . ?
O19 C16 C15 121.75(16) . . ?
O19 C16 C17 122.22(16) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.99(15) . . ?
C18 C17 H17 119.0 . . ?
C4 C18 H18 118.2 . . ?
C17 C18 C4 123.60(15) . . ?
C17 C18 H18 118.2 . . ?
C7 C20 H20A 108.6 . . ?
C7 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 C7 114.84(15) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21 117.5 . . ?
C22 C21 C20 124.9(2) . . ?
C22 C21 H21 117.5 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
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
O1 C2 1.4324(19) . ?
O1 C10 1.3649(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.506(2) . ?
C2 O11 1.396(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.555(2) . ?
C4 C5 1.531(2) . ?
C4 C14 1.502(2) . ?
C4 C18 1.510(2) . ?
C5 C6 1.395(2) . ?
C5 C10 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 C8 1.396(2) . ?
C7 C20 1.518(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 C10 1.393(2) . ?
C9 Br23 1.8997(15) . ?
O11 C12 1.441(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.497(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.332(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.469(2) . ?
C16 C17 1.468(2) . ?
C16 O19 1.226(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.331(2) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.491(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.314(3) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
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
O1 C2 C3 C4 -60.13(16) . . . . ?
O1 C2 O11 C12 -59.64(16) . . . . ?
C2 O1 C10 C5 -20.4(2) . . . . ?
C2 O1 C10 C9 161.84(14) . . . . ?
C2 C3 C4 C5 39.92(17) . . . . ?
C2 C3 C4 C14 158.70(13) . . . . ?
C2 C3 C4 C18 -79.78(16) . . . . ?
C2 O11 C12 C13 -171.69(15) . . . . ?
C3 C2 O11 C12 177.96(13) . . . . ?
C3 C4 C5 C6 168.40(14) . . . . ?
C3 C4 C5 C10 -11.53(19) . . . . ?
C3 C4 C14 C15 112.85(17) . . . . ?
C3 C4 C18 C17 -110.69(17) . . . . ?
C4 C5 C6 C7 179.62(14) . . . . ?
C4 C5 C10 O1 1.2(2) . . . . ?
C4 C5 C10 C9 178.86(14) . . . . ?
C4 C14 C15 C16 0.4(3) . . . . ?
C5 C4 C14 C15 -128.99(16) . . . . ?
C5 C4 C18 C17 129.54(16) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C5 C6 C7 C20 -176.27(15) . . . . ?
C6 C5 C10 O1 -178.76(14) . . . . ?
C6 C5 C10 C9 -1.1(2) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C6 C7 C20 C21 -154.50(16) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 Br23 179.07(12) . . . . ?
C7 C20 C21 C22 -123.3(2) . . . . ?
C8 C7 C20 C21 27.6(2) . . . . ?
C8 C9 C10 O1 179.17(14) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C10 O1 C2 C3 49.16(17) . . . . ?
C10 O1 C2 O11 -72.98(16) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
O11 C2 C3 C4 62.22(16) . . . . ?
C14 C4 C5 C6 51.74(18) . . . . ?
C14 C4 C5 C10 -128.19(15) . . . . ?
C14 C4 C18 C17 7.8(2) . . . . ?
C14 C15 C16 C17 7.6(2) . . . . ?
C14 C15 C16 O19 -171.58(17) . . . . ?
C15 C16 C17 C18 -7.7(2) . . . . ?
C16 C17 C18 C4 -0.3(2) . . . . ?
C18 C4 C5 C6 -71.01(18) . . . . ?
C18 C4 C5 C10 109.06(16) . . . . ?
C18 C4 C14 C15 -7.9(2) . . . . ?
O19 C16 C17 C18 171.54(16) . . . . ?
C20 C7 C8 C9 176.48(16) . . . . ?
Br23 C9 C10 O1 0.04(19) . . . . ?
Br23 C9 C10 C5 -177.80(11) . . . . ?
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
-0.0004 1.0000 0.0007 0.1015 -0.1029 -0.0708
0.0004 -1.0000 -0.0007 -0.1015 0.1029 0.0708
0.0000 -0.9999 0.9969 -0.1519 0.1222 -0.0584
-0.0000 0.9999 -0.9969 0.1519 -0.1222 0.0584
3.9997 -1.9949 -4.9956 0.6173 0.5575 0.3767
-4.9973 0.9931 1.0062 -0.6594 -0.6437 0.3139
0.0028 -2.0007 -5.9868 0.0992 0.0902 0.9170
