# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Min Shi'
_publ_contact_author_email       mshi@mail.sioc.ac.cn
loop_
_publ_author_name
'Min Shi'
'Yuan-Liang Yang'

data_cd201304
_database_code_depnum_ccdc_archive 'CCDC 779521'
#TrackingRef '- cd201304.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 Br N O3'
_chemical_formula_weight         440.33

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5465(15)
_cell_length_b                   13.646(2)
_cell_length_c                   14.694(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2114.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2506
_cell_measurement_theta_min      4.881
_cell_measurement_theta_max      40.510

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    1.966
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2039
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12821
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_sigmaI/netI    0.1151
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4811
_reflns_number_gt                2285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; calc
[0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/
[\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0356P)^2^+0.0000sin\q/\l]
where P = 0.33333Fo^2^ + 0.66667Fc^2^
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0688(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.033(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4811
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Br Br 0.64024(4) 0.25266(4) 1.07346(3) 0.0913(2) Uani 1 1 d . . .
O1 O 0.4705(2) 0.55621(18) 0.72167(18) 0.0598(7) Uani 1 1 d . . .
O2 O 0.6827(2) 0.54701(17) 0.72699(17) 0.0530(6) Uani 1 1 d . . .
O3 O 0.3011(3) 0.2309(2) 0.6356(2) 0.0860(9) Uani 1 1 d . . .
N1 N 0.7251(3) 0.4175(2) 0.6372(2) 0.0487(7) Uani 1 1 d . . .
C1 C 0.5661(3) 0.5171(3) 0.6965(3) 0.0500(9) Uani 1 1 d . . .
C2 C 0.7684(3) 0.4820(3) 0.6889(2) 0.0464(9) Uani 1 1 d . . .
C3 C 0.5868(3) 0.4316(2) 0.6328(2) 0.0442(8) Uani 1 1 d . . .
C4 C 0.5464(4) 0.4596(3) 0.5352(2) 0.0540(9) Uani 1 1 d . . .
H4 H 0.5753 0.4073 0.4945 0.065 Uiso 1 1 calc R . .
C5 C 0.6083(3) 0.5538(3) 0.5044(3) 0.0662(11) Uani 1 1 d . . .
H5A H 0.5709 0.6081 0.5361 0.099 Uiso 1 1 calc R . .
H5B H 0.5959 0.5619 0.4401 0.099 Uiso 1 1 calc R . .
H5C H 0.6975 0.5513 0.5173 0.099 Uiso 1 1 calc R . .
C6 C 0.4019(4) 0.4673(3) 0.5255(3) 0.0752(12) Uani 1 1 d . . .
H6A H 0.3691 0.5099 0.5719 0.113 Uiso 1 1 calc R . .
H6B H 0.3648 0.4035 0.5318 0.113 Uiso 1 1 calc R . .
H6C H 0.3814 0.4935 0.4666 0.113 Uiso 1 1 calc R . .
C7 C 0.5149(3) 0.3416(3) 0.6712(2) 0.0483(9) Uani 1 1 d . . .
H7 H 0.4254 0.3609 0.6724 0.058 Uiso 1 1 calc R . .
C8 C 0.5199(3) 0.2504(3) 0.6131(2) 0.0506(8) Uani 1 1 d . . .
C9 C 0.6210(4) 0.2210(3) 0.5680(3) 0.0757(12) Uani 1 1 d . . .
H9A H 0.6173 0.1647 0.5324 0.091 Uiso 1 1 calc R . .
H9B H 0.6961 0.2565 0.5719 0.091 Uiso 1 1 calc R . .
C10 C 0.3977(4) 0.1951(3) 0.6085(3) 0.0621(11) Uani 1 1 d . . .
C11 C 0.3993(4) 0.0944(3) 0.5674(3) 0.0836(14) Uani 1 1 d . . .
H11A H 0.3191 0.0630 0.5779 0.125 Uiso 1 1 calc R . .
H11B H 0.4656 0.0564 0.5949 0.125 Uiso 1 1 calc R . .
H11C H 0.4141 0.0993 0.5031 0.125 Uiso 1 1 calc R . .
C12 C 0.5490(3) 0.3194(2) 0.7699(2) 0.0434(8) Uani 1 1 d . . .
C13 C 0.4652(4) 0.3435(3) 0.8381(3) 0.0608(11) Uani 1 1 d . . .
H13 H 0.3887 0.3732 0.8231 0.073 Uiso 1 1 calc R . .
C14 C 0.4920(4) 0.3248(3) 0.9281(3) 0.0656(10) Uani 1 1 d . . .
H14 H 0.4344 0.3412 0.9735 0.079 Uiso 1 1 calc R . .
C15 C 0.6044(4) 0.2817(3) 0.9492(2) 0.0595(10) Uani 1 1 d . . .
C16 C 0.6909(3) 0.2578(3) 0.8836(3) 0.0654(10) Uani 1 1 d . . .
H16 H 0.7682 0.2298 0.8995 0.078 Uiso 1 1 calc R . .
C17 C 0.6621(3) 0.2758(3) 0.7944(2) 0.0567(10) Uani 1 1 d . . .
H17 H 0.7198 0.2583 0.7493 0.068 Uiso 1 1 calc R . .
C18 C 0.9014(3) 0.4987(3) 0.7148(3) 0.0523(9) Uani 1 1 d . . .
C19 C 0.9349(4) 0.5811(3) 0.7621(3) 0.0621(11) Uani 1 1 d . . .
H19 H 0.8737 0.6263 0.7799 0.075 Uiso 1 1 calc R . .
C20 C 1.0625(4) 0.5963(4) 0.7834(3) 0.0799(13) Uani 1 1 d . . .
H20 H 1.0868 0.6514 0.8162 0.096 Uiso 1 1 calc R . .
C21 C 1.1514(4) 0.5298(5) 0.7558(3) 0.0898(16) Uani 1 1 d . . .
H21 H 1.2365 0.5411 0.7684 0.108 Uiso 1 1 calc R . .
C22 C 1.1171(4) 0.4475(4) 0.7101(4) 0.0905(15) Uani 1 1 d . . .
H22 H 1.1786 0.4026 0.6921 0.109 Uiso 1 1 calc R . .
C23 C 0.9921(4) 0.4304(3) 0.6904(3) 0.0719(13) Uani 1 1 d . . .
H23 H 0.9683 0.3730 0.6607 0.086 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br 0.1044(4) 0.1065(4) 0.0631(2) 0.0044(3) -0.0146(2) -0.0256(3)
O1 0.0339(15) 0.0606(16) 0.0849(18) -0.0067(14) 0.0036(13) 0.0108(12)
O2 0.0301(14) 0.0545(15) 0.0745(16) -0.0096(13) 0.0010(12) -0.0010(11)
O3 0.0461(18) 0.079(2) 0.133(2) 0.007(2) -0.0065(17) -0.0158(17)
N1 0.0363(19) 0.0484(18) 0.0612(19) 0.0000(16) 0.0070(14) 0.0010(14)
C1 0.032(2) 0.052(2) 0.066(2) 0.0016(19) 0.0020(18) 0.0002(18)
C2 0.028(2) 0.046(2) 0.065(2) 0.0020(19) 0.0102(18) 0.0024(18)
C3 0.028(2) 0.047(2) 0.058(2) 0.0001(17) 0.0052(15) -0.0017(16)
C4 0.049(2) 0.057(2) 0.056(2) 0.0020(19) 0.0047(18) -0.0030(18)
C5 0.064(3) 0.059(3) 0.075(3) 0.009(2) 0.007(2) 0.0029(19)
C6 0.050(3) 0.100(3) 0.076(3) 0.017(2) -0.013(2) -0.005(2)
C7 0.030(2) 0.053(2) 0.062(2) 0.0038(18) 0.0044(16) 0.0005(16)
C8 0.042(2) 0.052(2) 0.0574(18) 0.001(2) -0.0025(15) -0.008(2)
C9 0.079(3) 0.059(3) 0.089(3) -0.019(2) 0.002(2) -0.005(2)
C10 0.062(3) 0.064(3) 0.061(2) 0.017(2) -0.021(2) -0.016(2)
C11 0.102(4) 0.082(3) 0.067(3) -0.004(3) -0.016(3) -0.035(3)
C12 0.030(2) 0.045(2) 0.055(2) -0.0040(17) 0.0074(16) -0.0049(15)
C13 0.045(2) 0.070(3) 0.067(3) 0.008(2) 0.011(2) 0.002(2)
C14 0.058(3) 0.072(3) 0.067(3) 0.000(2) 0.016(2) -0.007(2)
C15 0.060(3) 0.058(3) 0.061(2) 0.0012(18) 0.0012(18) -0.0196(19)
C16 0.049(2) 0.068(3) 0.079(3) 0.002(3) -0.0100(19) 0.008(2)
C17 0.042(2) 0.068(3) 0.060(2) 0.0038(19) 0.0017(17) 0.0131(19)
C18 0.029(2) 0.066(3) 0.063(2) 0.009(2) 0.0059(18) -0.0022(18)
C19 0.039(2) 0.065(3) 0.082(3) 0.006(2) -0.001(2) -0.003(2)
C20 0.049(3) 0.092(3) 0.099(3) 0.009(3) -0.011(3) -0.015(3)
C21 0.029(3) 0.138(5) 0.102(4) 0.012(3) -0.007(3) -0.001(3)
C22 0.041(3) 0.123(4) 0.108(4) 0.011(4) 0.000(3) 0.019(3)
C23 0.039(3) 0.089(3) 0.087(3) -0.003(3) 0.003(2) 0.003(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br C15 1.906(4) . ?
O1 C1 1.199(4) . ?
O2 C1 1.371(4) . ?
O2 C2 1.384(4) . ?
O3 C10 1.198(4) . ?
N1 C2 1.249(4) . ?
N1 C3 1.472(4) . ?
C1 C3 1.512(5) . ?
C2 C18 1.472(5) . ?
C3 C4 1.544(5) . ?
C3 C7 1.550(5) . ?
C4 C5 1.512(5) . ?
C4 C6 1.535(5) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.510(5) . ?
C7 C12 1.524(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.319(5) . ?
C8 C10 1.495(5) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.501(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.377(5) . ?
C12 C17 1.381(4) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(5) . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.369(5) . ?
C18 C23 1.383(5) . ?
C19 C20 1.396(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.358(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C1 O2 C2 105.2(3) . . ?
C2 N1 C3 107.3(3) . . ?
O1 C1 O2 121.4(3) . . ?
O1 C1 C3 131.0(3) . . ?
O2 C1 C3 107.6(3) . . ?
N1 C2 O2 117.3(3) . . ?
N1 C2 C18 127.9(3) . . ?
O2 C2 C18 114.8(3) . . ?
N1 C3 C1 102.5(3) . . ?
N1 C3 C4 110.3(3) . . ?
C1 C3 C4 110.1(3) . . ?
N1 C3 C7 111.5(3) . . ?
C1 C3 C7 108.4(3) . . ?
C4 C3 C7 113.5(3) . . ?
C5 C4 C6 110.0(3) . . ?
C5 C4 C3 111.7(3) . . ?
C6 C4 C3 112.2(3) . . ?
C5 C4 H4 107.6 . . ?
C6 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 111.5(3) . . ?
C8 C7 C3 115.4(3) . . ?
C12 C7 C3 112.8(3) . . ?
C8 C7 H7 105.4 . . ?
C12 C7 H7 105.4 . . ?
C3 C7 H7 105.4 . . ?
C9 C8 C10 121.4(4) . . ?
C9 C8 C7 124.3(3) . . ?
C10 C8 C7 114.3(3) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
O3 C10 C8 120.8(4) . . ?
O3 C10 C11 121.1(4) . . ?
C8 C10 C11 118.1(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 117.9(3) . . ?
C13 C12 C7 119.6(3) . . ?
C17 C12 C7 122.5(3) . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 118.6(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 121.7(4) . . ?
C14 C15 Br 118.8(3) . . ?
C16 C15 Br 119.5(3) . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C12 121.3(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C19 C18 C23 120.5(4) . . ?
C19 C18 C2 120.3(3) . . ?
C23 C18 C2 119.2(4) . . ?
C18 C19 C20 119.0(4) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 119.7(5) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 120.9(5) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.1(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 119.7(5) . . ?
C22 C23 H23 120.1 . . ?
C18 C23 H23 120.1 . . ?

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
C2 O2 C1 O1 176.1(3) . . . . ?
C2 O2 C1 C3 -2.8(3) . . . . ?
C3 N1 C2 O2 -0.2(4) . . . . ?
C3 N1 C2 C18 -179.7(3) . . . . ?
C1 O2 C2 N1 2.0(4) . . . . ?
C1 O2 C2 C18 -178.4(3) . . . . ?
C2 N1 C3 C1 -1.5(4) . . . . ?
C2 N1 C3 C4 115.7(3) . . . . ?
C2 N1 C3 C7 -117.2(3) . . . . ?
O1 C1 C3 N1 -176.1(4) . . . . ?
O2 C1 C3 N1 2.7(3) . . . . ?
O1 C1 C3 C4 66.6(5) . . . . ?
O2 C1 C3 C4 -114.6(3) . . . . ?
O1 C1 C3 C7 -58.1(5) . . . . ?
O2 C1 C3 C7 120.6(3) . . . . ?
N1 C3 C4 C5 -60.3(4) . . . . ?
C1 C3 C4 C5 52.1(4) . . . . ?
C7 C3 C4 C5 173.8(3) . . . . ?
N1 C3 C4 C6 175.6(3) . . . . ?
C1 C3 C4 C6 -72.0(4) . . . . ?
C7 C3 C4 C6 49.7(4) . . . . ?
N1 C3 C7 C8 -71.0(4) . . . . ?
C1 C3 C7 C8 177.0(3) . . . . ?
C4 C3 C7 C8 54.3(4) . . . . ?
N1 C3 C7 C12 58.8(4) . . . . ?
C1 C3 C7 C12 -53.2(4) . . . . ?
C4 C3 C7 C12 -175.9(3) . . . . ?
C12 C7 C8 C9 -91.5(4) . . . . ?
C3 C7 C8 C9 38.9(5) . . . . ?
C12 C7 C8 C10 89.8(3) . . . . ?
C3 C7 C8 C10 -139.8(3) . . . . ?
C9 C8 C10 O3 -166.4(4) . . . . ?
C7 C8 C10 O3 12.4(5) . . . . ?
C9 C8 C10 C11 12.6(5) . . . . ?
C7 C8 C10 C11 -168.7(3) . . . . ?
C8 C7 C12 C13 -123.8(3) . . . . ?
C3 C7 C12 C13 104.4(4) . . . . ?
C8 C7 C12 C17 56.3(4) . . . . ?
C3 C7 C12 C17 -75.5(4) . . . . ?
C17 C12 C13 C14 -0.2(6) . . . . ?
C7 C12 C13 C14 179.9(3) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C13 C14 C15 Br -178.5(3) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
Br C15 C16 C17 177.7(3) . . . . ?
C15 C16 C17 C12 1.5(6) . . . . ?
C13 C12 C17 C16 -0.7(5) . . . . ?
C7 C12 C17 C16 179.2(4) . . . . ?
N1 C2 C18 C19 170.8(4) . . . . ?
O2 C2 C18 C19 -8.7(5) . . . . ?
N1 C2 C18 C23 -9.0(6) . . . . ?
O2 C2 C18 C23 171.4(3) . . . . ?
C23 C18 C19 C20 1.6(6) . . . . ?
C2 C18 C19 C20 -178.2(4) . . . . ?
C18 C19 C20 C21 0.8(6) . . . . ?
C19 C20 C21 C22 -1.9(7) . . . . ?
C20 C21 C22 C23 0.5(8) . . . . ?
C21 C22 C23 C18 2.0(8) . . . . ?
C19 C18 C23 C22 -3.1(7) . . . . ?
C2 C18 C23 C22 176.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.044