#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/34/2223448.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_2223448
loop_
_publ_author_name
'Gunasekaran, B.'
'Kathiravan, S.'
'Raghunathan, R.'
'Chakkaravarthi, G.'
'Manivannan, V.'
_publ_section_title
;Methyl
 9-(4-bromophenyl)-8a,9,9a,10,11,12,13,14a-octahydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate
;
_journal_coeditor_code           IS2463
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2550
_journal_paper_doi               10.1107/S1600536809037994
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C27 H26 Br N O3'
_chemical_formula_moiety         'C27 H26 Br N O3'
_chemical_formula_sum            'C27 H26 Br N O3'
_chemical_formula_weight         492.40
_chemical_name_systematic
;Methyl 9-(4-bromophenyl)-8a,9,9a,10,11,12,13,14a-octahydro-8H-
benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate
;
_space_group_IT_number           147
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   18.4405(8)
_cell_length_b                   18.4405(8)
_cell_length_c                   11.4828(8)
_cell_measurement_reflns_used    4759
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.2
_cell_volume                     3381.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_sigmaI/netI    0.1095
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23085
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.79
_diffrn_reflns_theta_min         2.18
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    1.853
_exptl_absorpt_correction_T_max  0.7082
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5338
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.849
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2509
_reflns_number_total             5338
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2463.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223448
_cod_database_fobs_code          2223448
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
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
C C1 0.32587(18) 0.03952(17) -0.2836(3) 0.0450(7) Uani d U 1 . .
C C2 0.2679(2) 0.0537(2) -0.3441(3) 0.0616(9) Uani d U 1 . .
H H2 0.2401 0.0769 -0.3050 0.074 Uiso calc R 1 . .
C C3 0.2515(3) 0.0339(2) -0.4604(3) 0.0850(13) Uani d . 1 . .
H H3 0.2123 0.0432 -0.4982 0.102 Uiso calc R 1 . .
C C4 0.2927(3) 0.0004(2) -0.5221(3) 0.0859(13) Uani d . 1 . .
H H4 0.2821 -0.0115 -0.6011 0.103 Uiso calc R 1 . .
C C5 0.3479(3) -0.0149(2) -0.4667(3) 0.0786(12) Uani d . 1 . .
H H5 0.3752 -0.0375 -0.5082 0.094 Uiso calc R 1 . .
C C6 0.3654(2) 0.00269(18) -0.3465(3) 0.0564(9) Uani d . 1 . .
C C7 0.4228(2) -0.01415(18) -0.2873(3) 0.0627(10) Uani d . 1 . .
H H7 0.4519 -0.0349 -0.3286 0.075 Uiso calc R 1 . .
C C8 0.43567(19) -0.00053(17) -0.1725(3) 0.0513(8) Uani d . 1 . .
H H8 0.4704 -0.0156 -0.1336 0.062 Uiso calc R 1 . .
C C9 0.39688(17) 0.03636(16) -0.1111(2) 0.0384(7) Uani d . 1 . .
C C10 0.34630(16) 0.06057(15) -0.1639(2) 0.0356(7) Uani d . 1 . .
C C11 0.32309(16) 0.11839(16) -0.1002(2) 0.0341(6) Uani d . 1 . .
H H11 0.2669 0.1056 -0.1242 0.041 Uiso calc R 1 . .
C C12 0.32533(15) 0.11112(16) 0.0348(2) 0.0333(6) Uani d . 1 . .
C C13 0.34153(18) 0.04079(17) 0.0692(2) 0.0431(7) Uani d . 1 . .
H H13A 0.3526 0.0438 0.1522 0.052 Uiso calc R 1 . .
H H13B 0.2920 -0.0127 0.0531 0.052 Uiso calc R 1 . .
C C14 0.41242(18) 0.23382(17) -0.2399(2) 0.0434(7) Uani d . 1 . .
H H14A 0.3650 0.2180 -0.2912 0.052 Uiso calc R 1 . .
H H14B 0.4416 0.2053 -0.2663 0.052 Uiso calc R 1 . .
C C15 0.47016(18) 0.32660(18) -0.2460(2) 0.0477(8) Uani d . 1 . .
H H15A 0.4395 0.3550 -0.2268 0.057 Uiso calc R 1 . .
H H15B 0.4914 0.3422 -0.3247 0.057 Uiso calc R 1 . .
C C16 0.54293(18) 0.35396(18) -0.1621(3) 0.0492(8) Uani d . 1 . .
H H16A 0.5765 0.3293 -0.1850 0.059 Uiso calc R 1 . .
H H16B 0.5782 0.4144 -0.1644 0.059 Uiso calc R 1 . .
C C17 0.50984(18) 0.32634(16) -0.0398(2) 0.0425(7) Uani d . 1 . .
H H17A 0.5562 0.3404 0.0128 0.051 Uiso calc R 1 . .
H H17B 0.4815 0.3558 -0.0140 0.051 Uiso calc R 1 . .
C C18 0.44950(16) 0.23290(15) -0.0361(2) 0.0329(6) Uani d . 1 . .
H H18 0.4799 0.2029 -0.0508 0.039 Uiso calc R 1 . .
C C19 0.39796(15) 0.19968(16) 0.0742(2) 0.0323(6) Uani d . 1 . .
H H19 0.3722 0.2342 0.0882 0.039 Uiso calc R 1 . .
C C20 0.44263(16) 0.20142(16) 0.1853(2) 0.0326(6) Uani d . 1 . .
C C21 0.40965(17) 0.20588(17) 0.2912(2) 0.0395(7) Uani d . 1 . .
H H21 0.3612 0.2096 0.2925 0.047 Uiso calc R 1 . .
C C22 0.44673(19) 0.20491(18) 0.3956(2) 0.0454(8) Uani d . 1 . .
H H22 0.4232 0.2072 0.4662 0.054 Uiso calc R 1 . .
C C23 0.51857(18) 0.20047(17) 0.3933(2) 0.0414(7) Uani d . 1 . .
C C24 0.55532(18) 0.19869(17) 0.2895(3) 0.0461(8) Uani d . 1 . .
H H24 0.6053 0.1979 0.2888 0.055 Uiso calc R 1 . .
C C25 0.51612(17) 0.19814(17) 0.1866(2) 0.0426(7) Uani d . 1 . .
H H25 0.5397 0.1955 0.1162 0.051 Uiso calc R 1 . .
C C26 0.24417(18) 0.09807(19) 0.0883(3) 0.0456(7) Uani d U 1 . .
C C27 0.1435(2) 0.0356(3) 0.2332(4) 0.0985(14) Uani d . 1 . .
H H27A 0.1533 0.0860 0.2714 0.148 Uiso calc R 1 . .
H H27B 0.1240 -0.0091 0.2891 0.148 Uiso calc R 1 . .
H H27C 0.1021 0.0211 0.1735 0.148 Uiso calc R 1 . .
N N1 0.38286(13) 0.20806(12) -0.12185(17) 0.0301(5) Uani d . 1 . .
O O1 0.41141(11) 0.04609(11) 0.00670(17) 0.0446(5) Uani d . 1 . .
O O2 0.20524(13) 0.12926(15) 0.0531(2) 0.0685(7) Uani d U 1 . .
O O3 0.22148(12) 0.04877(13) 0.18093(17) 0.0569(6) Uani d . 1 . .
Br Br1 0.56763(2) 0.19502(2) 0.53512(3) 0.06620(16) Uani d . 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
C2 C1 C6 . . 117.4(3) ?
C2 C1 C10 . . 123.2(3) ?
C6 C1 C10 . . 119.4(3) ?
C3 C2 C1 . . 121.0(3) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 121.1(4) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C5 C4 C3 . . 119.4(4) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 121.5(4) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C7 C6 C1 . . 118.7(3) ?
C7 C6 C5 . . 121.8(3) ?
C1 C6 C5 . . 119.5(4) ?
C8 C7 C6 . . 120.8(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C7 C8 C9 . . 120.0(3) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C10 C9 O1 . . 121.1(2) ?
C10 C9 C8 . . 122.4(3) ?
O1 C9 C8 . . 116.5(3) ?
C9 C10 C1 . . 118.1(3) ?
C9 C10 C11 . . 119.7(2) ?
C1 C10 C11 . . 121.7(3) ?
N1 C11 C10 . . 112.9(2) ?
N1 C11 C12 . . 103.10(19) ?
C10 C11 C12 . . 112.9(2) ?
N1 C11 H11 . . 109.2 ?
C10 C11 H11 . . 109.2 ?
C12 C11 H11 . . 109.2 ?
C26 C12 C13 . . 111.0(2) ?
C26 C12 C11 . . 110.4(2) ?
C13 C12 C11 . . 110.9(2) ?
C26 C12 C19 . . 107.9(2) ?
C13 C12 C19 . . 112.5(2) ?
C11 C12 C19 . . 103.98(19) ?
O1 C13 C12 . . 111.4(2) ?
O1 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
O1 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
N1 C14 C15 . . 110.7(2) ?
N1 C14 H14A . . 109.5 ?
C15 C14 H14A . . 109.5 ?
N1 C14 H14B . . 109.5 ?
C15 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C14 C15 C16 . . 110.8(2) ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C17 C16 C15 . . 109.6(2) ?
C17 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
C17 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
C18 C17 C16 . . 110.6(2) ?
C18 C17 H17A . . 109.5 ?
C16 C17 H17A . . 109.5 ?
C18 C17 H17B . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.1 ?
N1 C18 C17 . . 111.3(2) ?
N1 C18 C19 . . 100.2(2) ?
C17 C18 C19 . . 116.0(2) ?
N1 C18 H18 . . 109.6 ?
C17 C18 H18 . . 109.6 ?
C19 C18 H18 . . 109.6 ?
C20 C19 C18 . . 118.2(2) ?
C20 C19 C12 . . 115.9(2) ?
C18 C19 C12 . . 102.47(19) ?
C20 C19 H19 . . 106.5 ?
C18 C19 H19 . . 106.5 ?
C12 C19 H19 . . 106.5 ?
C21 C20 C25 . . 117.6(2) ?
C21 C20 C19 . . 119.6(2) ?
C25 C20 C19 . . 122.8(2) ?
C20 C21 C22 . . 121.8(3) ?
C20 C21 H21 . . 119.1 ?
C22 C21 H21 . . 119.1 ?
C23 C22 C21 . . 118.9(3) ?
C23 C22 H22 . . 120.6 ?
C21 C22 H22 . . 120.6 ?
C22 C23 C24 . . 121.4(2) ?
C22 C23 Br1 . . 119.3(2) ?
C24 C23 Br1 . . 119.3(2) ?
C23 C24 C25 . . 118.5(3) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C24 C25 C20 . . 121.8(3) ?
C24 C25 H25 . . 119.1 ?
C20 C25 H25 . . 119.1 ?
O2 C26 O3 . . 122.9(3) ?
O2 C26 C12 . . 124.7(3) ?
O3 C26 C12 . . 112.4(3) ?
O3 C27 H27A . . 109.5 ?
O3 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O3 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C14 N1 C18 . . 114.1(2) ?
C14 N1 C11 . . 118.1(2) ?
C18 N1 C11 . . 106.10(18) ?
C9 O1 C13 . . 112.0(2) ?
C26 O3 C27 . . 113.0(3) ?
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
C1 C2 . 1.406(4) ?
C1 C6 . 1.417(4) ?
C1 C10 . 1.427(4) ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.390(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.344(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.418(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.416(5) ?
C7 C8 . 1.341(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.399(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.361(4) ?
C9 O1 . 1.374(3) ?
C10 C11 . 1.521(4) ?
C11 N1 . 1.479(3) ?
C11 C12 . 1.558(3) ?
C11 H11 . 0.9800 ?
C12 C26 . 1.521(4) ?
C12 C13 . 1.521(4) ?
C12 C19 . 1.574(3) ?
C13 O1 . 1.435(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 N1 . 1.450(3) ?
C14 C15 . 1.498(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.518(4) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 C17 . 1.515(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 C18 . 1.514(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 N1 . 1.459(3) ?
C18 C19 . 1.516(3) ?
C18 H18 . 0.9800 ?
C19 C20 . 1.511(3) ?
C19 H19 . 0.9800 ?
C20 C21 . 1.380(3) ?
C20 C25 . 1.387(4) ?
C21 C22 . 1.385(4) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.368(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.379(4) ?
C23 Br1 . 1.890(3) ?
C24 C25 . 1.383(4) ?
C24 H24 . 0.9300 ?
C25 H25 . 0.9300 ?
C26 O2 . 1.193(3) ?
C26 O3 . 1.324(3) ?
C27 O3 . 1.461(4) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
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
C15 H15B Br1 3_664 0.97 2.73 3.588(3) 147 y
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
C6 C1 C2 C3 . . . . -1.2(5) ?
C10 C1 C2 C3 . . . . 178.6(3) ?
C1 C2 C3 C4 . . . . -0.9(6) ?
C2 C3 C4 C5 . . . . 1.6(6) ?
C3 C4 C5 C6 . . . . -0.1(6) ?
C2 C1 C6 C7 . . . . -178.6(3) ?
C10 C1 C6 C7 . . . . 1.6(4) ?
C2 C1 C6 C5 . . . . 2.5(4) ?
C10 C1 C6 C5 . . . . -177.3(3) ?
C4 C5 C6 C7 . . . . 179.2(3) ?
C4 C5 C6 C1 . . . . -1.9(5) ?
C1 C6 C7 C8 . . . . 4.1(5) ?
C5 C6 C7 C8 . . . . -177.0(3) ?
C6 C7 C8 C9 . . . . -4.6(5) ?
C7 C8 C9 C10 . . . . -0.8(4) ?
C7 C8 C9 O1 . . . . 178.3(3) ?
O1 C9 C10 C1 . . . . -172.6(2) ?
C8 C9 C10 C1 . . . . 6.5(4) ?
O1 C9 C10 C11 . . . . 15.6(4) ?
C8 C9 C10 C11 . . . . -165.3(2) ?
C2 C1 C10 C9 . . . . 173.5(3) ?
C6 C1 C10 C9 . . . . -6.7(4) ?
C2 C1 C10 C11 . . . . -14.9(4) ?
C6 C1 C10 C11 . . . . 164.9(3) ?
C9 C10 C11 N1 . . . . 89.9(3) ?
C1 C10 C11 N1 . . . . -81.6(3) ?
C9 C10 C11 C12 . . . . -26.5(3) ?
C1 C10 C11 C12 . . . . 162.0(2) ?
N1 C11 C12 C26 . . . . 108.5(2) ?
C10 C11 C12 C26 . . . . -129.3(2) ?
N1 C11 C12 C13 . . . . -128.1(2) ?
C10 C11 C12 C13 . . . . -6.0(3) ?
N1 C11 C12 C19 . . . . -7.0(2) ?
C10 C11 C12 C19 . . . . 115.1(2) ?
C26 C12 C13 O1 . . . . 172.0(2) ?
C11 C12 C13 O1 . . . . 48.9(3) ?
C19 C12 C13 O1 . . . . -67.0(3) ?
N1 C14 C15 C16 . . . . 56.3(3) ?
C14 C15 C16 C17 . . . . -56.7(3) ?
C15 C16 C17 C18 . . . . 55.2(3) ?
C16 C17 C18 N1 . . . . -53.9(3) ?
C16 C17 C18 C19 . . . . -167.6(2) ?
N1 C18 C19 C20 . . . . 171.6(2) ?
C17 C18 C19 C20 . . . . -68.5(3) ?
N1 C18 C19 C12 . . . . 42.9(2) ?
C17 C18 C19 C12 . . . . 162.8(2) ?
C26 C12 C19 C20 . . . . 90.7(3) ?
C13 C12 C19 C20 . . . . -32.0(3) ?
C11 C12 C19 C20 . . . . -152.0(2) ?
C26 C12 C19 C18 . . . . -139.1(2) ?
C13 C12 C19 C18 . . . . 98.1(2) ?
C11 C12 C19 C18 . . . . -21.9(2) ?
C18 C19 C20 C21 . . . . 153.2(2) ?
C12 C19 C20 C21 . . . . -84.7(3) ?
C18 C19 C20 C25 . . . . -27.3(4) ?
C12 C19 C20 C25 . . . . 94.9(3) ?
C25 C20 C21 C22 . . . . -1.7(4) ?
C19 C20 C21 C22 . . . . 177.9(3) ?
C20 C21 C22 C23 . . . . 0.8(4) ?
C21 C22 C23 C24 . . . . 1.3(4) ?
C21 C22 C23 Br1 . . . . -177.7(2) ?
C22 C23 C24 C25 . . . . -2.5(4) ?
Br1 C23 C24 C25 . . . . 176.5(2) ?
C23 C24 C25 C20 . . . . 1.6(4) ?
C21 C20 C25 C24 . . . . 0.4(4) ?
C19 C20 C25 C24 . . . . -179.1(2) ?
C13 C12 C26 O2 . . . . -159.1(3) ?
C11 C12 C26 O2 . . . . -35.8(4) ?
C19 C12 C26 O2 . . . . 77.2(3) ?
C13 C12 C26 O3 . . . . 22.0(3) ?
C11 C12 C26 O3 . . . . 145.3(2) ?
C19 C12 C26 O3 . . . . -101.6(3) ?
C15 C14 N1 C18 . . . . -55.9(3) ?
C15 C14 N1 C11 . . . . 178.3(2) ?
C17 C18 N1 C14 . . . . 54.8(3) ?
C19 C18 N1 C14 . . . . 178.1(2) ?
C17 C18 N1 C11 . . . . -173.3(2) ?
C19 C18 N1 C11 . . . . -50.0(2) ?
C10 C11 N1 C14 . . . . 42.9(3) ?
C12 C11 N1 C14 . . . . 165.0(2) ?
C10 C11 N1 C18 . . . . -86.7(2) ?
C12 C11 N1 C18 . . . . 35.5(2) ?
C10 C9 O1 C13 . . . . 30.1(3) ?
C8 C9 O1 C13 . . . . -149.1(2) ?
C12 C13 O1 C9 . . . . -63.2(3) ?
O2 C26 O3 C27 . . . . 1.2(4) ?
C12 C26 O3 C27 . . . . -180.0(3) ?
