# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       catngdog@hotmail.com
loop_
_publ_author_name
U.Das
'Chan-Hui Huang'
'Wenwei Lin'

data_a13325
_database_code_depnum_ccdc_archive 'CCDC 865350'
#TrackingRef '- a13325 (5d).cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 Br N O2'
_chemical_formula_sum            'C19 H16 Br N O2'
_chemical_formula_weight         370.24
_chemical_absolute_configuration unk

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   'P 21 21 21'

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                   5.2806(2)
_cell_length_b                   8.1975(2)
_cell_length_c                   37.8235(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1637.29(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4725
_exptl_absorpt_correction_T_max  0.8635
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10765
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2830
_reflns_number_gt                2472
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+0.0792P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(10)
_refine_ls_number_reflns         2830
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_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
C1 C 0.8371(6) 0.1933(3) 0.79309(7) 0.0268(7) Uani 1 1 d . . .
C2 C 0.9245(6) 0.2175(3) 0.82732(7) 0.0285(8) Uani 1 1 d . . .
H2 H 1.0684 0.1601 0.8358 0.034 Uiso 1 1 calc R . .
C3 C 0.7979(6) 0.3268(3) 0.84879(8) 0.0272(7) Uani 1 1 d . . .
H3 H 0.8579 0.3449 0.8721 0.033 Uiso 1 1 calc R . .
C4 C 0.5861(5) 0.4105(3) 0.83720(7) 0.0227(7) Uani 1 1 d . . .
C5 C 0.5020(7) 0.3812(3) 0.80300(6) 0.0281(6) Uani 1 1 d . . .
H5 H 0.3566 0.4371 0.7945 0.034 Uiso 1 1 calc R . .
C6 C 0.6258(6) 0.2722(4) 0.78102(8) 0.0304(8) Uani 1 1 d . . .
H6 H 0.5646 0.2524 0.7578 0.036 Uiso 1 1 calc R . .
C7 C 0.4602(6) 0.5397(3) 0.85981(6) 0.0248(7) Uani 1 1 d . . .
H7 H 0.2935 0.5676 0.8488 0.030 Uiso 1 1 calc R . .
C8 C 0.6215(7) 0.6951(3) 0.86117(8) 0.0366(9) Uani 1 1 d . . .
H8 H 0.7953 0.6643 0.8693 0.044 Uiso 1 1 calc R . .
C9 C 0.6449(9) 0.7771(4) 0.82539(9) 0.0617(13) Uani 1 1 d . . .
H9A H 0.7513 0.8746 0.8276 0.093 Uiso 1 1 calc R . .
H9B H 0.4764 0.8086 0.8170 0.093 Uiso 1 1 calc R . .
H9C H 0.7222 0.7013 0.8085 0.093 Uiso 1 1 calc R . .
C10 C 0.5115(8) 0.8120(3) 0.88774(7) 0.0340(8) Uani 1 1 d . . .
H10 H 0.6181 0.9128 0.8882 0.041 Uiso 1 1 calc R . .
C11 C 0.4368(5) 0.5828(3) 0.92591(7) 0.0218(7) Uani 1 1 d . . .
C12 C 0.3995(5) 0.5368(3) 0.96353(7) 0.0215(6) Uani 1 1 d . . .
C13 C 0.5713(6) 0.5934(3) 0.98861(8) 0.0278(8) Uani 1 1 d . . .
H13 H 0.7073 0.6619 0.9815 0.033 Uiso 1 1 calc R . .
C14 C 0.5453(6) 0.5505(4) 1.02375(7) 0.0321(8) Uani 1 1 d . . .
H14 H 0.6657 0.5867 1.0407 0.039 Uiso 1 1 calc R . .
C15 C 0.3426(6) 0.4543(4) 1.03417(8) 0.0317(7) Uani 1 1 d . . .
H15 H 0.3240 0.4248 1.0583 0.038 Uiso 1 1 calc R . .
C16 C 0.1687(6) 0.4017(3) 1.00974(8) 0.0294(7) Uani 1 1 d . . .
H16 H 0.0290 0.3370 1.0171 0.035 Uiso 1 1 calc R . .
C17 C 0.1961(6) 0.4425(4) 0.97449(7) 0.0258(7) Uani 1 1 d . . .
H17 H 0.0751 0.4057 0.9577 0.031 Uiso 1 1 calc R . .
C18 C 0.4121(5) 0.4841(3) 0.89766(7) 0.0209(7) Uani 1 1 d . . .
C19 C 0.3452(6) 0.3167(4) 0.90267(7) 0.0224(7) Uani 1 1 d . . .
N1 N 0.2936(5) 0.1807(3) 0.90396(6) 0.0321(7) Uani 1 1 d . . .
O1 O 0.2668(5) 0.8548(2) 0.87875(5) 0.0431(6) Uani 1 1 d . . .
H1' H 0.2275 0.9547 0.8864 0.052 Uiso 1 1 d R . .
O2 O 0.5092(5) 0.74090(19) 0.92297(4) 0.0308(5) Uani 1 1 d . . .
Br1 Br 1.01469(7) 0.04674(4) 0.763013(7) 0.04022(12) Uani 1 1 d . . .

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
C1 0.033(2) 0.0248(16) 0.0223(17) -0.0047(13) 0.0117(14) -0.0046(15)
C2 0.0264(19) 0.0318(16) 0.0274(16) -0.0018(13) 0.0022(14) -0.0013(14)
C3 0.0323(19) 0.0312(16) 0.0180(16) -0.0042(13) -0.0005(14) -0.0029(16)
C4 0.0241(17) 0.0206(14) 0.0233(16) 0.0010(12) 0.0050(13) -0.0065(12)
C5 0.0280(17) 0.0314(14) 0.0250(15) 0.0015(11) -0.0011(18) -0.0028(18)
C6 0.036(2) 0.0353(17) 0.0199(16) -0.0035(14) 0.0006(14) -0.0093(16)
C7 0.0303(19) 0.0216(13) 0.0226(14) 0.0024(11) -0.0001(14) -0.0035(18)
C8 0.051(2) 0.0246(16) 0.0346(19) -0.0028(14) 0.0125(16) -0.0090(16)
C9 0.116(4) 0.0310(19) 0.039(2) 0.0012(16) 0.028(2) -0.020(2)
C10 0.051(2) 0.0199(13) 0.0312(16) 0.0022(11) 0.007(2) -0.006(2)
C11 0.0171(18) 0.0218(14) 0.0266(16) -0.0011(12) 0.0017(13) 0.0016(12)
C12 0.0234(16) 0.0154(13) 0.0255(16) -0.0021(12) 0.0011(13) 0.0052(13)
C13 0.0271(19) 0.0238(15) 0.0323(18) -0.0031(13) -0.0011(14) -0.0020(13)
C14 0.032(2) 0.0365(15) 0.0277(17) -0.0060(13) -0.0100(14) 0.004(2)
C15 0.038(2) 0.0359(16) 0.0207(16) -0.0019(15) 0.0024(14) 0.0108(18)
C16 0.0307(19) 0.0318(17) 0.0257(18) 0.0002(14) 0.0053(15) 0.0007(15)
C17 0.0208(16) 0.0309(16) 0.0257(17) -0.0056(14) -0.0016(13) 0.0017(16)
C18 0.0221(17) 0.0166(13) 0.0241(15) 0.0008(11) 0.0021(12) 0.0010(12)
C19 0.0256(18) 0.0266(16) 0.0149(16) -0.0007(12) -0.0004(13) 0.0012(14)
N1 0.0472(19) 0.0246(14) 0.0243(15) -0.0017(11) 0.0033(13) 0.0013(14)
O1 0.0623(18) 0.0228(11) 0.0444(14) -0.0045(10) -0.0036(13) 0.0083(12)
O2 0.0457(14) 0.0208(9) 0.0258(10) -0.0023(7) 0.0036(13) -0.0096(13)
Br1 0.0460(2) 0.04062(18) 0.03403(18) -0.01375(13) 0.0120(2) -0.0020(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
C1 C6 1.368(4) . ?
C1 C2 1.389(4) . ?
C1 Br1 1.902(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 C7 1.515(4) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C18 1.524(4) . ?
C7 C8 1.534(4) . ?
C7 H7 1.0000 . ?
C8 C10 1.506(4) . ?
C8 C9 1.516(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O1 1.382(4) . ?
C10 O2 1.454(3) . ?
C10 H10 1.0000 . ?
C11 C18 1.347(4) . ?
C11 O2 1.356(3) . ?
C11 C12 1.485(4) . ?
C12 C17 1.387(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.429(4) . ?
C19 N1 1.149(3) . ?
O1 H1' 0.8926 . ?

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
C6 C1 C2 121.0(3) . . ?
C6 C1 Br1 120.1(2) . . ?
C2 C1 Br1 118.9(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C7 121.5(3) . . ?
C5 C4 C7 120.4(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C7 C18 113.2(2) . . ?
C4 C7 C8 110.8(2) . . ?
C18 C7 C8 108.0(2) . . ?
C4 C7 H7 108.2 . . ?
C18 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C10 C8 C9 110.2(2) . . ?
C10 C8 C7 109.7(3) . . ?
C9 C8 C7 112.6(3) . . ?
C10 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 O2 108.6(3) . . ?
O1 C10 C8 111.0(3) . . ?
O2 C10 C8 111.1(2) . . ?
O1 C10 H10 108.7 . . ?
O2 C10 H10 108.7 . . ?
C8 C10 H10 108.7 . . ?
C18 C11 O2 122.4(2) . . ?
C18 C11 C12 126.5(2) . . ?
O2 C11 C12 111.0(2) . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 C11 122.0(2) . . ?
C13 C12 C11 118.8(3) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C11 C18 C19 119.7(2) . . ?
C11 C18 C7 123.3(2) . . ?
C19 C18 C7 116.9(2) . . ?
N1 C19 C18 174.8(3) . . ?
C10 O1 H1' 111.7 . . ?
C11 O2 C10 117.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050

# Attachment '- a13353 (3b).cif'

data_a13353
_database_code_depnum_ccdc_archive 'CCDC 865351'
#TrackingRef '- a13353 (3b).cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Br N O2'
_chemical_formula_sum            'C22 H20 Br N O2'
_chemical_formula_weight         410.30
_chemical_absolute_configuration unk

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   'P 21 21 21'

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                   5.5785(4)
_cell_length_b                   15.6744(8)
_cell_length_c                   22.2663(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1947.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4222
_exptl_absorpt_correction_T_max  0.9390
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12357
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_sigmaI/netI    0.1249
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3425
_reflns_number_gt                1906
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(13)
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.001
_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
C1 C 0.3690(14) 0.8421(3) 0.0733(2) 0.072(2) Uani 1 1 d . . .
C2 C 0.1818(12) 0.7914(3) 0.0561(2) 0.070(2) Uani 1 1 d . B .
H2 H 0.0871 0.8065 0.0223 0.084 Uiso 1 1 calc R . .
C3 C 0.1303(10) 0.7173(3) 0.0884(2) 0.0500(15) Uani 1 1 d . . .
H3 H -0.0007 0.6822 0.0769 0.060 Uiso 1 1 calc R B .
C4 C 0.2697(10) 0.6951(2) 0.13706(19) 0.0351(13) Uani 1 1 d . B .
C5 C 0.4533(10) 0.7480(3) 0.15360(18) 0.0508(16) Uani 1 1 d . . .
H5 H 0.5478 0.7335 0.1876 0.061 Uiso 1 1 calc R B .
C6 C 0.5053(12) 0.8216(3) 0.1226(2) 0.0654(19) Uani 1 1 d . B .
H6 H 0.6332 0.8575 0.1350 0.079 Uiso 1 1 calc R . .
C7 C 0.2162(9) 0.6140(2) 0.17239(18) 0.0346(13) Uani 1 1 d . . .
H7 H 0.0684 0.5871 0.1555 0.041 Uiso 1 1 calc R B .
C8 C 0.4249(8) 0.5494(2) 0.16763(16) 0.0303(11) Uani 1 1 d . B .
H8 H 0.5761 0.5793 0.1794 0.036 Uiso 1 1 calc R . .
C9 C 0.4574(9) 0.5145(2) 0.10412(17) 0.0418(14) Uani 1 1 d . . .
H9A H 0.4950 0.5620 0.0764 0.050 Uiso 1 1 calc R B .
H9B H 0.3063 0.4876 0.0905 0.050 Uiso 1 1 calc R . .
C10 C 0.6599(9) 0.4488(3) 0.10230(18) 0.0460(14) Uani 1 1 d . B .
H10A H 0.8136 0.4772 0.1120 0.055 Uiso 1 1 calc R . .
H10B H 0.6725 0.4250 0.0612 0.055 Uiso 1 1 calc R . .
C11 C 0.6164(10) 0.3762(3) 0.14684(19) 0.0434(14) Uani 1 1 d . . .
H11A H 0.7540 0.3364 0.1462 0.052 Uiso 1 1 calc R B .
H11B H 0.4709 0.3441 0.1351 0.052 Uiso 1 1 calc R . .
C12 C 0.5847(9) 0.4123(2) 0.21018(19) 0.0423(13) Uani 1 1 d . B .
H12A H 0.5481 0.3652 0.2384 0.051 Uiso 1 1 calc R . .
H12B H 0.7357 0.4397 0.2233 0.051 Uiso 1 1 calc R . .
C13 C 0.3848(10) 0.4765(3) 0.2114(2) 0.0421(13) Uani 1 1 d . . .
C14 C 0.2619(10) 0.5832(3) 0.2827(2) 0.0489(14) Uani 1 1 d . . .
C15 C 0.1748(9) 0.6319(3) 0.2385(2) 0.0363(13) Uani 1 1 d . B .
C16 C 0.0343(10) 0.7063(3) 0.25375(17) 0.0385(13) Uani 1 1 d . . .
C17 C 0.2509(11) 0.6043(4) 0.3476(2) 0.0630(18) Uani 1 1 d . A .
C18 C 0.343(3) 0.6568(6) 0.3695(5) 0.046(3) Uiso 0.50 1 d P A 1
H18 H 0.4424 0.6925 0.3457 0.056 Uiso 0.50 1 calc PR A 1
C19 C 0.322(3) 0.6754(7) 0.4321(5) 0.052(3) Uiso 0.50 1 d P A 1
H19 H 0.4008 0.7235 0.4490 0.063 Uiso 0.50 1 calc PR A 1
C20 C 0.192(2) 0.6243(6) 0.4659(5) 0.043(3) Uiso 0.50 1 d P A 1
H20 H 0.1771 0.6365 0.5075 0.052 Uiso 0.50 1 calc PR A 1
C21 C 0.077(2) 0.5546(6) 0.4432(4) 0.063(3) Uiso 0.50 1 d P A 1
H21 H -0.0166 0.5192 0.4688 0.076 Uiso 0.50 1 calc PR A 1
C22 C 0.0964(18) 0.5354(5) 0.3824(4) 0.039(2) Uiso 0.50 1 d P A 1
H22 H 0.0257 0.4869 0.3640 0.046 Uiso 0.50 1 calc PR A 1
C18' C 0.479(2) 0.6372(5) 0.3802(4) 0.039(3) Uiso 0.50 1 d P A 2
H18' H 0.6257 0.6410 0.3585 0.046 Uiso 0.50 1 calc PR A 2
C19' C 0.475(2) 0.6607(5) 0.4390(4) 0.042(3) Uiso 0.50 1 d P A 2
H19' H 0.6217 0.6743 0.4585 0.051 Uiso 0.50 1 calc PR A 2
C20' C 0.264(2) 0.6654(6) 0.4712(5) 0.047(3) Uiso 0.50 1 d P A 2
H20' H 0.2672 0.6784 0.5129 0.057 Uiso 0.50 1 calc PR A 2
C21' C 0.049(2) 0.6511(6) 0.4425(4) 0.062(3) Uiso 0.50 1 d P A 2
H21' H -0.0989 0.6578 0.4633 0.074 Uiso 0.50 1 calc PR A 2
C22' C 0.052(2) 0.6257(5) 0.3799(4) 0.055(3) Uiso 0.50 1 d P A 2
H22' H -0.0973 0.6237 0.3596 0.066 Uiso 0.50 1 calc PR A 2
N1 N -0.0801(8) 0.7661(2) 0.26281(16) 0.0502(13) Uani 1 1 d . B .
O1 O 0.1609(6) 0.44173(19) 0.20065(15) 0.0585(10) Uani 1 1 d . B .
H1' H 0.1559 0.3828 0.2160 0.070 Uiso 1 1 d R . .
O2 O 0.3865(6) 0.5109(2) 0.27341(13) 0.0565(10) Uani 1 1 d . B .
Br1 Br 0.5156(14) 0.93607(15) 0.03289(12) 0.0603(14) Uani 0.509(10) 1 d P B 3
Br1' Br 0.3563(15) 0.95045(17) 0.02808(8) 0.0651(13) Uani 0.491(10) 1 d P B 4

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
C1 0.145(7) 0.030(3) 0.039(3) -0.005(2) 0.021(4) -0.025(4)
C2 0.125(7) 0.042(3) 0.044(3) 0.013(2) -0.014(3) 0.004(3)
C3 0.064(5) 0.038(2) 0.048(3) 0.006(2) -0.015(3) -0.008(3)
C4 0.049(4) 0.024(2) 0.032(3) -0.002(2) -0.001(3) -0.002(2)
C5 0.060(5) 0.051(3) 0.041(3) -0.002(2) -0.002(3) -0.028(3)
C6 0.098(6) 0.049(3) 0.049(3) -0.007(3) 0.007(4) -0.034(3)
C7 0.035(4) 0.034(2) 0.035(3) 0.006(2) -0.005(2) -0.008(2)
C8 0.022(3) 0.036(2) 0.033(2) 0.0067(19) 0.001(2) -0.007(2)
C9 0.057(4) 0.037(2) 0.031(3) 0.0009(19) -0.005(3) 0.004(3)
C10 0.057(4) 0.046(2) 0.035(3) 0.004(2) -0.005(2) 0.006(3)
C11 0.037(4) 0.043(3) 0.050(3) 0.009(2) -0.007(3) 0.004(3)
C12 0.025(4) 0.057(3) 0.045(3) 0.020(2) 0.008(3) 0.010(2)
C13 0.034(4) 0.051(3) 0.041(3) 0.018(2) 0.006(3) 0.011(3)
C14 0.036(4) 0.071(3) 0.040(3) 0.009(3) 0.012(3) 0.007(3)
C15 0.028(4) 0.041(3) 0.039(3) 0.007(2) 0.000(2) 0.002(2)
C16 0.036(4) 0.052(3) 0.028(3) 0.002(2) -0.006(2) -0.014(3)
C17 0.056(5) 0.099(5) 0.034(3) 0.018(3) 0.010(3) 0.035(4)
N1 0.046(4) 0.051(2) 0.053(3) -0.010(2) -0.005(2) 0.004(2)
O1 0.021(2) 0.0476(17) 0.107(3) 0.042(2) 0.001(2) 0.0023(18)
O2 0.043(3) 0.084(2) 0.042(2) 0.0248(18) 0.0139(17) 0.038(2)
Br1 0.090(4) 0.0329(7) 0.0576(9) 0.0120(6) 0.0171(13) -0.0051(11)
Br1' 0.089(4) 0.0402(8) 0.0659(9) 0.0204(7) -0.0099(11) -0.0060(13)

_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
C1 C6 1.373(7) . ?
C1 C2 1.368(8) . ?
C1 Br1 1.910(5) . ?
C1 Br1' 1.975(5) . ?
C2 C3 1.396(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(6) . ?
C4 C7 1.524(5) . ?
C5 C6 1.376(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C15 1.515(5) . ?
C7 C8 1.547(6) . ?
C7 H7 1.0000 . ?
C8 C13 1.518(5) . ?
C8 C9 1.527(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.529(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.529(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.529(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.503(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O1 1.384(5) . ?
C13 O2 1.481(5) . ?
C14 C15 1.338(6) . ?
C14 O2 1.346(5) . ?
C14 C17 1.483(6) . ?
C15 C16 1.445(6) . ?
C16 N1 1.152(5) . ?
C17 C18 1.085(10) . ?
C17 C22' 1.363(12) . ?
C17 C18' 1.556(12) . ?
C17 C22 1.585(10) . ?
C18 C19 1.429(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.318(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.365(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(11) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C18' C19' 1.361(11) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.380(15) . ?
C19' H19' 0.9500 . ?
C20' C21' 1.380(16) . ?
C20' H20' 0.9500 . ?
C21' C22' 1.450(12) . ?
C21' H21' 0.9500 . ?
C22' H22' 0.9500 . ?
O1 H1' 0.9857 . ?

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
C6 C1 C2 120.7(4) . . ?
C6 C1 Br1 108.7(5) . . ?
C2 C1 Br1 130.0(5) . . ?
C6 C1 Br1' 129.0(5) . . ?
C2 C1 Br1' 109.2(5) . . ?
Br1 C1 Br1' 27.43(8) . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 C7 120.9(4) . . ?
C3 C4 C7 120.4(4) . . ?
C4 C5 C6 122.1(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C15 C7 C4 112.1(3) . . ?
C15 C7 C8 107.6(3) . . ?
C4 C7 C8 111.3(4) . . ?
C15 C7 H7 108.6 . . ?
C4 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C13 C8 C9 110.1(3) . . ?
C13 C8 C7 109.7(4) . . ?
C9 C8 C7 112.8(3) . . ?
C13 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
C8 C9 C10 110.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 111.5(4) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.0(3) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 110.5(4) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O1 C13 O2 108.1(4) . . ?
O1 C13 C12 113.7(4) . . ?
O2 C13 C12 104.8(4) . . ?
O1 C13 C8 108.5(4) . . ?
O2 C13 C8 108.9(3) . . ?
C12 C13 C8 112.5(4) . . ?
C15 C14 O2 123.7(4) . . ?
C15 C14 C17 125.0(5) . . ?
O2 C14 C17 111.1(4) . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 C7 123.6(4) . . ?
C16 C15 C7 117.5(4) . . ?
N1 C16 C15 176.4(5) . . ?
C18 C17 C22' 87.7(9) . . ?
C18 C17 C14 126.0(9) . . ?
C22' C17 C14 127.1(7) . . ?
C18 C17 C18' 32.0(7) . . ?
C22' C17 C18' 109.8(7) . . ?
C14 C17 C18' 119.7(6) . . ?
C18 C17 C22 123.6(8) . . ?
C22' C17 C22 57.7(5) . . ?
C14 C17 C22 110.3(6) . . ?
C18' C17 C22 116.3(6) . . ?
C17 C18 C19 123.7(12) . . ?
C17 C18 H18 118.1 . . ?
C19 C18 H18 118.1 . . ?
C20 C19 C18 118.5(11) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C21 122.4(12) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C22 119.7(10) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 111.9(7) . . ?
C21 C22 H22 124.1 . . ?
C17 C22 H22 124.1 . . ?
C19' C18' C17 121.7(10) . . ?
C19' C18' H18' 119.2 . . ?
C17 C18' H18' 119.2 . . ?
C18' C19' C20' 121.9(11) . . ?
C18' C19' H19' 119.0 . . ?
C20' C19' H19' 119.0 . . ?
C19' C20' C21' 119.6(11) . . ?
C19' C20' H20' 120.2 . . ?
C21' C20' H20' 120.2 . . ?
C20' C21' C22' 118.5(11) . . ?
C20' C21' H21' 120.7 . . ?
C22' C21' H21' 120.7 . . ?
C17 C22' C21' 126.0(11) . . ?
C17 C22' H22' 117.0 . . ?
C21' C22' H22' 117.0 . . ?
C13 O1 H1' 109.6 . . ?
C14 O2 C13 116.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051