#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230190.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230190
loop_
_publ_author_name
'Khalilov, Ali N.'
'Abdelhamid, Antar A.'
'Gurbanov, Atash V.'
'Ng, Seik Weng'
_publ_section_title
;
 9-(5-Bromo-2-hydroxyphenyl)-10-(2-hydroxypropyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
;
_journal_coeditor_code           XU5192
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1146
_journal_paper_doi               10.1107/S1600536811013481
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H32 Br N O4'
_chemical_formula_moiety         'C26 H32 Br N O4'
_chemical_formula_sum            'C26 H32 Br N O4'
_chemical_formula_weight         502.44
_chemical_name_systematic
;
9-(5-Bromo-2-hydroxyphenyl)-10-(2-hydroxypropyl)-3,3,6,6-tetramethyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.303(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6685(4)
_cell_length_b                   16.8190(5)
_cell_length_c                   14.1260(5)
_cell_measurement_reflns_used    3308
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3647
_cell_measurement_theta_min      2.3239
_cell_volume                     2432.76(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11939
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_T_max  0.9189
_exptl_absorpt_correction_T_min  0.7246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.662
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5402
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0549P)²+1.4767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                3939
_reflns_number_total             5402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5192.cif
_cod_data_source_block           I
_cod_original_cell_volume        2432.76(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230190
_cod_database_fobs_code          2230190
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.00011(3) 0.07288(2) 0.84090(3) 0.02822(14) Uani d . 1 . .
O O1 0.6038(2) 0.22434(18) 1.01434(16) 0.0322(6) Uani d . 1 . .
H H1 0.5337 0.2333 0.9706 0.039 Uiso calc R 1 . .
O O2 0.3796(2) 0.25478(16) 0.88504(17) 0.0306(6) Uani d . 1 . .
O O3 0.7557(3) 0.41222(15) 0.86062(17) 0.0284(6) Uani d . 1 A .
O O4 0.6148(10) 0.0597(4) 0.6070(6) 0.0224(9) Uani d PDU 0.636(6) A 1
H H4 0.6748 0.0648 0.6598 0.027 Uiso calc PR 0.636(6) A 1
O O4' 0.6669(7) 0.0829(4) 0.4503(4) 0.0224(9) Uani d PD 0.364 A 2
H H4' 0.7173 0.0435 0.4608 0.027 Uiso calc PR 0.364(6) A 2
N N1 0.5582(3) 0.22319(18) 0.61661(19) 0.0209(6) Uani d . 1 A .
C C1 0.6924(4) 0.1925(2) 0.9722(2) 0.0253(8) Uani d . 1 . .
C C2 0.7829(4) 0.1395(2) 1.0291(2) 0.0291(9) Uani d . 1 . .
H H2 0.7803 0.1273 1.0942 0.035 Uiso calc R 1 . .
C C3 0.8759(4) 0.1044(2) 0.9923(2) 0.0274(8) Uani d . 1 . .
H H3 0.9380 0.0686 1.0315 0.033 Uiso calc R 1 . .
C C4 0.8772(3) 0.1223(2) 0.8975(2) 0.0231(8) Uani d . 1 . .
C C5 0.7896(3) 0.1759(2) 0.8406(2) 0.0206(7) Uani d . 1 . .
H H5 0.7928 0.1873 0.7754 0.025 Uiso calc R 1 . .
C C6 0.6975(3) 0.2134(2) 0.8771(2) 0.0195(7) Uani d . 1 . .
C C7 0.6024(3) 0.2741(2) 0.8146(2) 0.0218(7) Uani d . 1 . .
H H7 0.5812 0.3146 0.8595 0.026 Uiso calc R 1 . .
C C8 0.4774(3) 0.2344(2) 0.7571(2) 0.0214(7) Uani d . 1 . .
C C9 0.3703(3) 0.2291(2) 0.8002(2) 0.0245(8) Uani d . 1 . .
C C10 0.2455(4) 0.1933(2) 0.7402(3) 0.0316(9) Uani d . 1 . .
H H10A 0.1952 0.2335 0.6935 0.038 Uiso calc R 1 . .
H H10B 0.1923 0.1768 0.7841 0.038 Uiso calc R 1 . .
C C11 0.2724(4) 0.1208(2) 0.6826(3) 0.0320(9) Uani d . 1 . .
C C12 0.3568(3) 0.1482(2) 0.6168(2) 0.0260(8) Uani d . 1 . .
H H12A 0.3945 0.1007 0.5937 0.031 Uiso calc R 1 . .
H H12B 0.2999 0.1750 0.5580 0.031 Uiso calc R 1 . .
C C13 0.4664(3) 0.2038(2) 0.6662(2) 0.0213(8) Uani d . 1 . .
C C14 0.3435(4) 0.0568(2) 0.7541(3) 0.0392(10) Uani d . 1 . .
H H14A 0.3604 0.0108 0.7169 0.059 Uiso calc R 1 . .
H H14B 0.2893 0.0404 0.7964 0.059 Uiso calc R 1 . .
H H14C 0.4266 0.0780 0.7951 0.059 Uiso calc R 1 . .
C C15 0.1428(4) 0.0876(3) 0.6174(3) 0.0461(12) Uani d . 1 . .
H H15A 0.1603 0.0414 0.5808 0.069 Uiso calc R 1 . .
H H15B 0.0980 0.1286 0.5709 0.069 Uiso calc R 1 . .
H H15C 0.0876 0.0715 0.6590 0.069 Uiso calc R 1 . .
C C16 0.5558(3) 0.1821(2) 0.5232(2) 0.0253(8) Uani d D 1 . .
H H16A 0.5847 0.2201 0.4799 0.030 Uiso calc PR 0.636(6) A 1
H H16B 0.4645 0.1671 0.4893 0.030 Uiso calc PR 0.636(6) A 1
H H16C 0.5683 0.2211 0.4740 0.030 Uiso calc PR 0.364(6) A 2
H H16D 0.4706 0.1554 0.4958 0.030 Uiso calc PR 0.364(6) A 2
C C17 0.6394(8) 0.1092(5) 0.5351(6) 0.035(2) Uani d PDU 0.636(6) A 1
H H17 0.6079 0.0794 0.4715 0.042 Uiso calc PR 0.636(6) A 1
C C17' 0.6674(17) 0.1202(11) 0.5460(9) 0.035(2) Uani d PD 0.364 A 2
H H17' 0.7542 0.1415 0.5846 0.042 Uiso calc PR 0.364(6) A 2
C C18 0.7835(8) 0.1139(5) 0.5556(6) 0.064(3) Uani d PDU 0.636(6) A 1
H H18A 0.8061 0.1579 0.5180 0.096 Uiso calc PR 0.636(6) A 1
H H18B 0.8165 0.0639 0.5361 0.096 Uiso calc PR 0.636(6) A 1
H H18C 0.8230 0.1229 0.6262 0.096 Uiso calc PR 0.636(6) A 1
C C18' 0.613(4) 0.0541(18) 0.598(2) 0.064(3) Uani d PD 0.364 A 2
H H18D 0.6726 0.0085 0.6100 0.096 Uiso calc PR 0.364(6) A 2
H H18E 0.5270 0.0377 0.5569 0.096 Uiso calc PR 0.364(6) A 2
H H18F 0.6050 0.0740 0.6615 0.096 Uiso calc PR 0.364(6) A 2
C C19 0.6444(3) 0.2861(2) 0.6502(2) 0.0207(7) Uani d . 1 . .
C C20 0.7162(3) 0.3212(2) 0.5820(2) 0.0221(7) Uani d . 1 A .
H H20A 0.6538 0.3531 0.5310 0.027 Uiso calc R 1 . .
H H20B 0.7475 0.2772 0.5480 0.027 Uiso calc R 1 . .
C C21 0.8325(3) 0.3738(2) 0.6323(2) 0.0208(7) Uani d . 1 . .
C C22 0.7910(4) 0.4311(2) 0.7019(2) 0.0241(8) Uani d . 1 A .
H H22A 0.8672 0.4633 0.7376 0.029 Uiso calc R 1 . .
H H22B 0.7236 0.4677 0.6628 0.029 Uiso calc R 1 . .
C C23 0.7371(3) 0.3877(2) 0.7761(2) 0.0222(8) Uani d . 1 . .
C C24 0.6607(3) 0.3159(2) 0.7426(2) 0.0208(7) Uani d . 1 A .
C C25 0.8732(4) 0.4213(2) 0.5529(3) 0.0273(8) Uani d . 1 A .
H H25A 0.9004 0.3846 0.5085 0.041 Uiso calc R 1 . .
H H25B 0.9460 0.4566 0.5845 0.041 Uiso calc R 1 . .
H H25C 0.7991 0.4531 0.5150 0.041 Uiso calc R 1 . .
C C26 0.9486(3) 0.3234(2) 0.6901(2) 0.0258(8) Uani d . 1 A .
H H26A 0.9746 0.2869 0.6449 0.039 Uiso calc R 1 . .
H H26B 0.9233 0.2928 0.7409 0.039 Uiso calc R 1 . .
H H26C 1.0220 0.3584 0.7214 0.039 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
C17' O4' H4' . . 109.5 ?
C13 N1 C19 . . 119.7(3) ?
C13 N1 C16 . . 119.9(3) ?
C19 N1 C16 . . 120.1(3) ?
O1 C1 C2 . . 117.0(3) ?
O1 C1 C6 . . 122.5(3) ?
C2 C1 C6 . . 120.4(3) ?
C3 C2 C1 . . 120.9(3) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 118.6(3) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C3 C4 C5 . . 121.3(3) ?
C3 C4 Br1 . . 120.5(3) ?
C5 C4 Br1 . . 118.2(2) ?
C6 C5 C4 . . 121.0(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C1 . . 117.7(3) ?
C5 C6 C7 . . 120.9(3) ?
C1 C6 C7 . . 121.4(3) ?
C24 C7 C8 . . 108.3(3) ?
C24 C7 C6 . . 111.6(3) ?
C8 C7 C6 . . 110.9(3) ?
C24 C7 H7 . . 108.7 ?
C8 C7 H7 . . 108.7 ?
C6 C7 H7 . . 108.7 ?
C13 C8 C9 . . 120.6(3) ?
C13 C8 C7 . . 120.3(3) ?
C9 C8 C7 . . 119.0(3) ?
O2 C9 C8 . . 121.7(3) ?
O2 C9 C10 . . 120.1(3) ?
C8 C9 C10 . . 118.2(3) ?
C9 C10 C11 . . 110.6(3) ?
C9 C10 H10A . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
C14 C11 C12 . . 110.2(3) ?
C14 C11 C15 . . 109.7(3) ?
C12 C11 C15 . . 109.2(3) ?
C14 C11 C10 . . 110.0(3) ?
C12 C11 C10 . . 108.2(3) ?
C15 C11 C10 . . 109.6(4) ?
C13 C12 C11 . . 114.6(3) ?
C13 C12 H12A . . 108.6 ?
C11 C12 H12A . . 108.6 ?
C13 C12 H12B . . 108.6 ?
C11 C12 H12B . . 108.6 ?
H12A C12 H12B . . 107.6 ?
C8 C13 N1 . . 120.0(3) ?
C8 C13 C12 . . 121.5(3) ?
N1 C13 C12 . . 118.5(3) ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 C15 H15A . . 109.5 ?
C11 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C11 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N1 C16 C17 . . 114.8(4) ?
N1 C16 C17' . . 107.9(5) ?
C17 C16 C17' . . 13.0(11) ?
N1 C16 H16A . . 108.6 ?
C17 C16 H16A . . 108.6 ?
C17' C16 H16A . . 102.0 ?
N1 C16 H16B . . 108.6 ?
C17 C16 H16B . . 108.6 ?
H16A C16 H16B . . 107.5 ?
N1 C16 H16C . . 110.1 ?
C17 C16 H16C . . 115.3 ?
C17' C16 H16C . . 110.1 ?
N1 C16 H16D . . 110.1 ?
C17' C16 H16D . . 110.1 ?
H16C C16 H16D . . 108.4 ?
O4 C17 C18 . . 106.6(7) ?
O4 C17 C16 . . 110.0(6) ?
C18 C17 C16 . . 122.0(8) ?
O4 C17 H17 . . 105.7 ?
C18 C17 H17 . . 105.7 ?
C16 C17 H17 . . 105.7 ?
O4' C17' C18' . . 103.1(17) ?
O4' C17' C16 . . 106.7(8) ?
C18' C17' C16 . . 102(2) ?
O4' C17' H17' . . 114.4 ?
C18' C17' H17' . . 114.4 ?
C16 C17' H17' . . 114.4 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17' C18' H18D . . 109.5 ?
C17' C18' H18E . . 109.5 ?
H18D C18' H18E . . 109.5 ?
C17' C18' H18F . . 109.5 ?
H18D C18' H18F . . 109.5 ?
H18E C18' H18F . . 109.5 ?
C24 C19 N1 . . 120.0(3) ?
C24 C19 C20 . . 121.1(3) ?
N1 C19 C20 . . 119.0(3) ?
C19 C20 C21 . . 115.0(3) ?
C19 C20 H20A . . 108.5 ?
C21 C20 H20A . . 108.5 ?
C19 C20 H20B . . 108.5 ?
C21 C20 H20B . . 108.5 ?
H20A C20 H20B . . 107.5 ?
C20 C21 C22 . . 108.7(3) ?
C20 C21 C26 . . 111.0(3) ?
C22 C21 C26 . . 110.0(3) ?
C20 C21 C25 . . 108.8(3) ?
C22 C21 C25 . . 109.5(3) ?
C26 C21 C25 . . 109.0(3) ?
C23 C22 C21 . . 112.1(3) ?
C23 C22 H22A . . 109.2 ?
C21 C22 H22A . . 109.2 ?
C23 C22 H22B . . 109.2 ?
C21 C22 H22B . . 109.2 ?
H22A C22 H22B . . 107.9 ?
O3 C23 C24 . . 121.2(3) ?
O3 C23 C22 . . 121.5(3) ?
C24 C23 C22 . . 117.4(3) ?
C19 C24 C23 . . 121.6(3) ?
C19 C24 C7 . . 120.6(3) ?
C23 C24 C7 . . 117.8(3) ?
C21 C25 H25A . . 109.5 ?
C21 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C21 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C21 C26 H26A . . 109.5 ?
C21 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C21 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C4 . 1.908(4) ?
O1 C1 . 1.360(4) ?
O1 H1 . 0.8400 ?
O2 C9 . 1.251(4) ?
O3 C23 . 1.226(4) ?
O4 C17 . 1.394(7) ?
O4 H4 . 0.8400 ?
O4' C17' . 1.488(10) ?
O4' H4' . 0.8400 ?
N1 C13 . 1.393(4) ?
N1 C19 . 1.394(4) ?
N1 C16 . 1.483(4) ?
C1 C2 . 1.391(5) ?
C1 C6 . 1.405(5) ?
C2 C3 . 1.376(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.376(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.382(5) ?
C5 C6 . 1.383(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.532(5) ?
C7 C24 . 1.507(4) ?
C7 C8 . 1.509(5) ?
C7 H7 . 1.0000 ?
C8 C13 . 1.357(5) ?
C8 C9 . 1.440(5) ?
C9 C10 . 1.490(5) ?
C10 C11 . 1.538(6) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C14 . 1.525(5) ?
C11 C12 . 1.535(5) ?
C11 C15 . 1.535(5) ?
C12 C13 . 1.507(5) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C17 . 1.499(7) ?
C16 C17' . 1.547(9) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C16 H16C . 0.9900 ?
C16 H16D . 0.9900 ?
C17 C18 . 1.484(8) ?
C17 H17 . 1.0000 ?
C17' C18' . 1.535(10) ?
C17' H17' . 1.0000 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C18' H18D . 0.9800 ?
C18' H18E . 0.9800 ?
C18' H18F . 0.9800 ?
C19 C24 . 1.364(5) ?
C19 C20 . 1.509(4) ?
C20 C21 . 1.526(5) ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.529(5) ?
C21 C26 . 1.533(5) ?
C21 C25 . 1.536(5) ?
C22 C23 . 1.516(5) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.459(5) ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 . 0.84 1.78 2.621(4) 176 yes
C10 H10A O1 4_565 0.99 2.54 3.417(5) 147 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 180.0(3) ?
C6 C1 C2 C3 . . . . -2.3(6) ?
C1 C2 C3 C4 . . . . -0.5(6) ?
C2 C3 C4 C5 . . . . 1.8(5) ?
C2 C3 C4 Br1 . . . . -177.9(3) ?
C3 C4 C5 C6 . . . . -0.1(5) ?
Br1 C4 C5 C6 . . . . 179.5(3) ?
C4 C5 C6 C1 . . . . -2.6(5) ?
C4 C5 C6 C7 . . . . 178.7(3) ?
O1 C1 C6 C5 . . . . -178.6(3) ?
C2 C1 C6 C5 . . . . 3.8(5) ?
O1 C1 C6 C7 . . . . 0.1(5) ?
C2 C1 C6 C7 . . . . -177.6(3) ?
C5 C6 C7 C24 . . . . -28.8(4) ?
C1 C6 C7 C24 . . . . 152.6(3) ?
C5 C6 C7 C8 . . . . 92.0(4) ?
C1 C6 C7 C8 . . . . -86.6(4) ?
C24 C7 C8 C13 . . . . 34.3(4) ?
C6 C7 C8 C13 . . . . -88.5(4) ?
C24 C7 C8 C9 . . . . -146.0(3) ?
C6 C7 C8 C9 . . . . 91.2(4) ?
C13 C8 C9 O2 . . . . 177.8(3) ?
C7 C8 C9 O2 . . . . -1.9(5) ?
C13 C8 C9 C10 . . . . -3.3(5) ?
C7 C8 C9 C10 . . . . 177.0(3) ?
O2 C9 C10 C11 . . . . -140.9(3) ?
C8 C9 C10 C11 . . . . 40.3(4) ?
C9 C10 C11 C14 . . . . 62.2(4) ?
C9 C10 C11 C12 . . . . -58.2(4) ?
C9 C10 C11 C15 . . . . -177.2(3) ?
C14 C11 C12 C13 . . . . -77.2(4) ?
C15 C11 C12 C13 . . . . 162.3(3) ?
C10 C11 C12 C13 . . . . 43.1(4) ?
C9 C8 C13 N1 . . . . 166.7(3) ?
C7 C8 C13 N1 . . . . -13.6(5) ?
C9 C8 C13 C12 . . . . -13.7(5) ?
C7 C8 C13 C12 . . . . 165.9(3) ?
C19 N1 C13 C8 . . . . -13.5(5) ?
C16 N1 C13 C8 . . . . 172.4(3) ?
C19 N1 C13 C12 . . . . 166.9(3) ?
C16 N1 C13 C12 . . . . -7.2(5) ?
C11 C12 C13 C8 . . . . -8.0(5) ?
C11 C12 C13 N1 . . . . 171.6(3) ?
C13 N1 C16 C17 . . . . -91.6(6) ?
C19 N1 C16 C17 . . . . 94.3(6) ?
C13 N1 C16 C17' . . . . -103.5(10) ?
C19 N1 C16 C17' . . . . 82.4(10) ?
N1 C16 C17 O4 . . . . 49.4(8) ?
C17' C16 C17 O4 . . . . 110(4) ?
N1 C16 C17 C18 . . . . -76.5(8) ?
C17' C16 C17 C18 . . . . -16(3) ?
N1 C16 C17' O4' . . . . -177.2(10) ?
C17 C16 C17' O4' . . . . 59(3) ?
N1 C16 C17' C18' . . . . 74.8(16) ?
C17 C16 C17' C18' . . . . -49(4) ?
C13 N1 C19 C24 . . . . 15.8(5) ?
C16 N1 C19 C24 . . . . -170.1(3) ?
C13 N1 C19 C20 . . . . -163.1(3) ?
C16 N1 C19 C20 . . . . 11.1(4) ?
C24 C19 C20 C21 . . . . 16.5(5) ?
N1 C19 C20 C21 . . . . -164.7(3) ?
C19 C20 C21 C22 . . . . -46.6(4) ?
C19 C20 C21 C26 . . . . 74.4(4) ?
C19 C20 C21 C25 . . . . -165.8(3) ?
C20 C21 C22 C23 . . . . 55.7(4) ?
C26 C21 C22 C23 . . . . -65.9(4) ?
C25 C21 C22 C23 . . . . 174.4(3) ?
C21 C22 C23 O3 . . . . 144.8(3) ?
C21 C22 C23 C24 . . . . -35.9(4) ?
N1 C19 C24 C23 . . . . -172.3(3) ?
C20 C19 C24 C23 . . . . 6.5(5) ?
N1 C19 C24 C7 . . . . 9.1(5) ?
C20 C19 C24 C7 . . . . -172.1(3) ?
O3 C23 C24 C19 . . . . -177.0(3) ?
C22 C23 C24 C19 . . . . 3.7(5) ?
O3 C23 C24 C7 . . . . 1.6(5) ?
C22 C23 C24 C7 . . . . -177.7(3) ?
C8 C7 C24 C19 . . . . -31.9(4) ?
C6 C7 C24 C19 . . . . 90.4(4) ?
C8 C7 C24 C23 . . . . 149.4(3) ?
C6 C7 C24 C23 . . . . -88.2(4) ?
