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


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#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_cd29453
_database_code_depnum_ccdc_archive 'CCDC 865414'
#TrackingRef '9387_web_deposit_cif_file_1_Ting-ShunZhu_1328158437.4k-cd29453.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H30 Br N O2'
_chemical_formula_weight         576.51

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3964(10)
_cell_length_b                   11.1200(12)
_cell_length_c                   14.1931(16)
_cell_angle_alpha                80.855(2)
_cell_angle_beta                 76.993(2)
_cell_angle_gamma                80.832(2)
_cell_volume                     1414.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2416
_cell_measurement_theta_min      4.486
_cell_measurement_theta_max      48.271

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3557
_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            7500
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5205
_reflns_number_gt                3259
_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 w=1/[\s^2^(Fo^2^)+(0.0760P)^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     SHELXL
_refine_ls_extinction_coef       0.0142(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.901
_refine_ls_shift/su_max          0.008
_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 0.58000(5) -0.01014(3) -0.36835(3) 0.0880(2) Uani 1 1 d . . .
N1 N 0.2196(2) 0.3670(2) 0.12095(16) 0.0453(6) Uani 1 1 d . . .
O1 O 0.2161(3) 0.0625(2) 0.1225(2) 0.0809(8) Uani 1 1 d . . .
O2 O 0.0469(2) 0.20163(18) 0.06804(15) 0.0563(5) Uani 1 1 d . . .
C1 C 0.1996(3) 0.3301(3) 0.2282(2) 0.0503(7) Uani 1 1 d . . .
H1A H 0.2365 0.3899 0.2561 0.060 Uiso 1 1 calc R . .
H1B H 0.2590 0.2516 0.2400 0.060 Uiso 1 1 calc R . .
C2 C 0.0433(3) 0.3190(2) 0.28032(19) 0.0481(7) Uani 1 1 d . . .
C3 C -0.0013(4) 0.2019(3) 0.3194(2) 0.0616(9) Uani 1 1 d . . .
H3 H 0.0673 0.1319 0.3132 0.074 Uiso 1 1 calc R . .
C4 C -0.1416(4) 0.1907(3) 0.3655(2) 0.0669(10) Uani 1 1 d . . .
H4 H -0.1667 0.1135 0.3935 0.080 Uiso 1 1 calc R . .
C5 C -0.2504(4) 0.2925(3) 0.3721(2) 0.0575(8) Uani 1 1 d . . .
C6 C -0.3987(5) 0.2814(4) 0.4143(3) 0.0811(11) Uani 1 1 d . . .
H6 H -0.4258 0.2048 0.4424 0.097 Uiso 1 1 calc R . .
C7 C -0.5031(5) 0.3810(5) 0.4145(3) 0.0887(12) Uani 1 1 d . . .
H7 H -0.6006 0.3720 0.4437 0.106 Uiso 1 1 calc R . .
C8 C -0.4660(4) 0.4969(4) 0.3715(3) 0.0760(10) Uani 1 1 d . . .
H8 H -0.5392 0.5637 0.3698 0.091 Uiso 1 1 calc R . .
C9 C -0.3231(3) 0.5122(3) 0.3322(2) 0.0574(8) Uani 1 1 d . . .
H9 H -0.2993 0.5901 0.3052 0.069 Uiso 1 1 calc R . .
C10 C -0.2098(3) 0.4112(3) 0.33191(19) 0.0496(7) Uani 1 1 d . . .
C11 C -0.0594(3) 0.4221(2) 0.29048(19) 0.0424(7) Uani 1 1 d . . .
C12 C -0.0066(3) 0.5448(2) 0.25274(19) 0.0412(6) Uani 1 1 d . . .
C13 C -0.0225(3) 0.6384(2) 0.3135(2) 0.0448(7) Uani 1 1 d . . .
C14 C -0.0872(3) 0.6241(3) 0.4141(2) 0.0548(8) Uani 1 1 d . . .
H14 H -0.1219 0.5504 0.4430 0.066 Uiso 1 1 calc R . .
C15 C -0.0996(4) 0.7161(3) 0.4692(2) 0.0692(9) Uani 1 1 d . . .
H15 H -0.1419 0.7041 0.5353 0.083 Uiso 1 1 calc R . .
C16 C -0.0499(4) 0.8283(3) 0.4281(3) 0.0735(10) Uani 1 1 d . . .
H16 H -0.0608 0.8913 0.4662 0.088 Uiso 1 1 calc R . .
C17 C 0.0145(4) 0.8445(3) 0.3322(3) 0.0635(9) Uani 1 1 d . . .
H17 H 0.0475 0.9194 0.3050 0.076 Uiso 1 1 calc R . .
C18 C 0.0330(3) 0.7513(2) 0.2725(2) 0.0483(7) Uani 1 1 d . . .
C19 C 0.1075(3) 0.7647(3) 0.1744(2) 0.0526(8) Uani 1 1 d . . .
H19 H 0.1436 0.8383 0.1468 0.063 Uiso 1 1 calc R . .
C20 C 0.1275(3) 0.6719(3) 0.1197(2) 0.0512(7) Uani 1 1 d . . .
H20 H 0.1797 0.6820 0.0557 0.061 Uiso 1 1 calc R . .
C21 C 0.0707(3) 0.5604(2) 0.1578(2) 0.0422(6) Uani 1 1 d . . .
C22 C 0.0986(3) 0.4578(2) 0.0959(2) 0.0461(7) Uani 1 1 d . . .
H22A H 0.0102 0.4187 0.1062 0.055 Uiso 1 1 calc R . .
H22B H 0.1232 0.4907 0.0276 0.055 Uiso 1 1 calc R . .
C23 C 0.2789(3) 0.2675(2) 0.0598(2) 0.0462(7) Uani 1 1 d . . .
C24 C 0.4330(3) 0.2140(3) 0.0769(2) 0.0519(7) Uani 1 1 d . . .
H24A H 0.4237 0.1619 0.1390 0.062 Uiso 1 1 calc R . .
H24B H 0.4814 0.1633 0.0264 0.062 Uiso 1 1 calc R . .
C25 C 0.5271(3) 0.3111(3) 0.0769(2) 0.0607(8) Uani 1 1 d . . .
H25 H 0.5398 0.3704 0.0226 0.073 Uiso 1 1 calc R . .
C26 C 0.5922(4) 0.3182(4) 0.1469(3) 0.0772(10) Uani 1 1 d . . .
H26A H 0.5820 0.2604 0.2023 0.093 Uiso 1 1 calc R . .
H26B H 0.6490 0.3812 0.1418 0.093 Uiso 1 1 calc R . .
C27 C 0.1809(3) 0.1635(3) 0.0858(2) 0.0490(7) Uani 1 1 d . . .
C28 C -0.0599(4) 0.1162(3) 0.0985(3) 0.0672(9) Uani 1 1 d . . .
H28A H -0.0283 0.0468 0.0629 0.101 Uiso 1 1 calc R . .
H28B H -0.1535 0.1558 0.0860 0.101 Uiso 1 1 calc R . .
H28C H -0.0690 0.0889 0.1671 0.101 Uiso 1 1 calc R . .
C29 C 0.2864(3) 0.3213(3) -0.0491(2) 0.0470(7) Uani 1 1 d . . .
H29A H 0.1866 0.3495 -0.0581 0.056 Uiso 1 1 calc R . .
H29B H 0.3385 0.3927 -0.0623 0.056 Uiso 1 1 calc R . .
C30 C 0.3591(3) 0.2365(2) -0.1240(2) 0.0441(7) Uani 1 1 d . . .
C31 C 0.2831(4) 0.1573(3) -0.1516(2) 0.0644(9) Uani 1 1 d . . .
H31 H 0.1853 0.1528 -0.1207 0.077 Uiso 1 1 calc R . .
C32 C 0.3466(4) 0.0838(3) -0.2236(3) 0.0725(10) Uani 1 1 d . . .
H32 H 0.2926 0.0305 -0.2406 0.087 Uiso 1 1 calc R . .
C33 C 0.4892(4) 0.0904(3) -0.2691(2) 0.0560(8) Uani 1 1 d . . .
C34 C 0.5682(4) 0.1691(3) -0.2444(2) 0.0651(9) Uani 1 1 d . . .
H34 H 0.6658 0.1734 -0.2757 0.078 Uiso 1 1 calc R . .
C35 C 0.5024(3) 0.2420(3) -0.1729(2) 0.0626(9) Uani 1 1 d . . .
H35 H 0.5562 0.2965 -0.1572 0.075 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 0.1244(4) 0.0731(3) 0.0657(3) -0.0284(2) -0.0071(2) -0.0080(2)
N1 0.0540(14) 0.0392(13) 0.0410(13) -0.0011(10) -0.0125(11) -0.0010(11)
O1 0.0782(16) 0.0438(13) 0.122(2) 0.0168(14) -0.0378(15) -0.0131(12)
O2 0.0474(12) 0.0524(12) 0.0677(14) 0.0029(10) -0.0124(10) -0.0126(10)
C1 0.064(2) 0.0430(16) 0.0441(16) -0.0018(13) -0.0191(15) -0.0007(14)
C2 0.073(2) 0.0390(16) 0.0344(15) -0.0009(12) -0.0143(14) -0.0121(15)
C3 0.098(3) 0.0394(17) 0.0472(18) -0.0033(14) -0.0140(18) -0.0101(17)
C4 0.109(3) 0.048(2) 0.0474(19) 0.0016(15) -0.0119(19) -0.036(2)
C5 0.080(2) 0.058(2) 0.0396(17) -0.0067(14) -0.0032(15) -0.0341(18)
C6 0.101(3) 0.087(3) 0.061(2) -0.012(2) 0.005(2) -0.055(3)
C7 0.072(3) 0.120(4) 0.076(3) -0.024(3) 0.015(2) -0.050(3)
C8 0.061(2) 0.091(3) 0.075(2) -0.021(2) 0.0027(18) -0.019(2)
C9 0.058(2) 0.064(2) 0.0509(18) -0.0118(15) -0.0026(15) -0.0196(17)
C10 0.065(2) 0.0499(18) 0.0370(15) -0.0080(13) -0.0052(14) -0.0219(16)
C11 0.0570(18) 0.0381(15) 0.0347(14) -0.0018(12) -0.0103(13) -0.0158(13)
C12 0.0445(16) 0.0358(15) 0.0447(16) -0.0008(12) -0.0115(13) -0.0100(12)
C13 0.0485(17) 0.0391(15) 0.0476(16) -0.0011(13) -0.0122(13) -0.0095(13)
C14 0.070(2) 0.0483(17) 0.0485(18) -0.0079(14) -0.0108(15) -0.0158(15)
C15 0.095(3) 0.068(2) 0.0500(19) -0.0148(17) -0.0174(18) -0.0163(19)
C16 0.102(3) 0.054(2) 0.076(3) -0.0249(19) -0.028(2) -0.0126(19)
C17 0.078(2) 0.0388(17) 0.080(3) -0.0092(17) -0.0240(19) -0.0133(16)
C18 0.0488(17) 0.0377(16) 0.0603(19) -0.0008(14) -0.0162(15) -0.0093(13)
C19 0.0545(18) 0.0358(16) 0.065(2) 0.0067(15) -0.0095(15) -0.0150(13)
C20 0.0476(17) 0.0465(17) 0.0534(18) 0.0048(15) -0.0049(14) -0.0073(14)
C21 0.0409(16) 0.0398(15) 0.0434(15) 0.0021(12) -0.0100(12) -0.0031(12)
C22 0.0529(17) 0.0432(16) 0.0402(15) -0.0003(13) -0.0109(13) -0.0030(13)
C23 0.0505(17) 0.0428(16) 0.0443(16) -0.0026(13) -0.0098(13) -0.0061(13)
C24 0.0523(18) 0.0522(17) 0.0500(17) -0.0073(14) -0.0127(14) 0.0005(14)
C25 0.0487(18) 0.070(2) 0.061(2) -0.0019(17) -0.0125(16) -0.0060(16)
C26 0.071(2) 0.090(3) 0.078(3) -0.021(2) -0.017(2) -0.019(2)
C27 0.0512(19) 0.0463(18) 0.0491(17) -0.0055(14) -0.0112(14) -0.0043(14)
C28 0.064(2) 0.067(2) 0.075(2) -0.0051(18) -0.0132(17) -0.0272(17)
C29 0.0481(17) 0.0454(16) 0.0472(17) -0.0042(13) -0.0098(13) -0.0071(13)
C30 0.0445(17) 0.0454(16) 0.0429(16) -0.0015(13) -0.0125(13) -0.0064(13)
C31 0.0526(19) 0.082(2) 0.063(2) -0.0215(18) -0.0034(16) -0.0233(17)
C32 0.085(3) 0.077(2) 0.067(2) -0.0219(19) -0.0092(19) -0.041(2)
C33 0.071(2) 0.0505(18) 0.0462(17) -0.0053(14) -0.0143(16) -0.0034(16)
C34 0.0497(19) 0.085(2) 0.066(2) -0.0319(19) -0.0028(16) -0.0150(17)
C35 0.056(2) 0.074(2) 0.067(2) -0.0270(18) -0.0086(16) -0.0227(16)

_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 C33 1.901(3) . ?
N1 C22 1.463(3) . ?
N1 C23 1.475(3) . ?
N1 C1 1.489(3) . ?
O1 C27 1.189(3) . ?
O2 C27 1.330(3) . ?
O2 C28 1.441(3) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C11 1.379(4) . ?
C2 C3 1.421(4) . ?
C3 C4 1.349(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(5) . ?
C5 C10 1.427(4) . ?
C6 C7 1.357(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(4) . ?
C11 C12 1.503(4) . ?
C12 C21 1.377(4) . ?
C12 C13 1.424(4) . ?
C13 C14 1.414(4) . ?
C13 C18 1.424(4) . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.407(4) . ?
C19 C20 1.353(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.503(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.533(4) . ?
C23 C27 1.540(4) . ?
C23 C29 1.556(4) . ?
C24 C25 1.500(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.298(5) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9300 . ?
C26 H26B 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.508(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.369(4) . ?
C30 C35 1.375(4) . ?
C31 C32 1.379(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.358(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(4) . ?
C34 C35 1.374(4) . ?
C34 H34 0.9300 . ?
C35 H35 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
C22 N1 C23 119.1(2) . . ?
C22 N1 C1 111.6(2) . . ?
C23 N1 C1 115.9(2) . . ?
C27 O2 C28 117.2(2) . . ?
N1 C1 C2 114.9(2) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C11 C2 C3 118.9(3) . . ?
C11 C2 C1 120.7(2) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 C10 118.8(3) . . ?
C6 C5 C10 118.9(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 123.2(3) . . ?
C9 C10 C5 118.1(3) . . ?
C11 C10 C5 118.7(3) . . ?
C2 C11 C10 120.8(2) . . ?
C2 C11 C12 117.4(2) . . ?
C10 C11 C12 121.8(2) . . ?
C21 C12 C13 120.2(2) . . ?
C21 C12 C11 117.2(2) . . ?
C13 C12 C11 122.4(2) . . ?
C14 C13 C12 123.4(2) . . ?
C14 C13 C18 117.7(3) . . ?
C12 C13 C18 118.9(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 122.3(3) . . ?
C17 C18 C13 118.8(3) . . ?
C19 C18 C13 118.9(3) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C12 C21 C20 119.6(3) . . ?
C12 C21 C22 120.4(2) . . ?
C20 C21 C22 120.0(3) . . ?
N1 C22 C21 110.3(2) . . ?
N1 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
N1 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
N1 C23 C24 108.9(2) . . ?
N1 C23 C27 111.3(2) . . ?
C24 C23 C27 108.4(2) . . ?
N1 C23 C29 108.9(2) . . ?
C24 C23 C29 110.3(2) . . ?
C27 C23 C29 109.0(2) . . ?
C25 C24 C23 112.9(2) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 124.8(3) . . ?
C26 C25 H25 117.6 . . ?
C24 C25 H25 117.6 . . ?
C25 C26 H26A 120.0 . . ?
C25 C26 H26B 120.0 . . ?
H26A C26 H26B 120.0 . . ?
O1 C27 O2 123.1(3) . . ?
O1 C27 C23 124.9(3) . . ?
O2 C27 C23 111.9(2) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C23 116.9(2) . . ?
C30 C29 H29A 108.1 . . ?
C23 C29 H29A 108.1 . . ?
C30 C29 H29B 108.1 . . ?
C23 C29 H29B 108.1 . . ?
H29A C29 H29B 107.3 . . ?
C31 C30 C35 117.0(3) . . ?
C31 C30 C29 121.8(3) . . ?
C35 C30 C29 121.1(3) . . ?
C30 C31 C32 122.2(3) . . ?
C30 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
C33 C32 C31 119.1(3) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 120.4(3) . . ?
C32 C33 Br 120.1(3) . . ?
C34 C33 Br 119.5(3) . . ?
C33 C34 C35 119.5(3) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C30 121.8(3) . . ?
C34 C35 H35 119.1 . . ?
C30 C35 H35 119.1 . . ?

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
C22 N1 C1 C2 37.9(3) . . . . ?
C23 N1 C1 C2 -102.9(3) . . . . ?
N1 C1 C2 C11 -69.9(3) . . . . ?
N1 C1 C2 C3 109.6(3) . . . . ?
C11 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 3.4(5) . . . . ?
C3 C4 C5 C6 175.8(3) . . . . ?
C3 C4 C5 C10 -2.1(5) . . . . ?
C4 C5 C6 C7 -176.1(4) . . . . ?
C10 C5 C6 C7 1.9(5) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C6 C7 C8 C9 -2.7(6) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C8 C9 C10 C11 179.0(3) . . . . ?
C8 C9 C10 C5 1.3(4) . . . . ?
C4 C5 C10 C9 175.1(3) . . . . ?
C6 C5 C10 C9 -3.0(4) . . . . ?
C4 C5 C10 C11 -2.7(4) . . . . ?
C6 C5 C10 C11 179.2(3) . . . . ?
C3 C2 C11 C10 -5.2(4) . . . . ?
C1 C2 C11 C10 174.3(3) . . . . ?
C3 C2 C11 C12 176.9(3) . . . . ?
C1 C2 C11 C12 -3.5(4) . . . . ?
C9 C10 C11 C2 -171.2(3) . . . . ?
C5 C10 C11 C2 6.4(4) . . . . ?
C9 C10 C11 C12 6.5(4) . . . . ?
C5 C10 C11 C12 -175.8(3) . . . . ?
C2 C11 C12 C21 52.5(3) . . . . ?
C10 C11 C12 C21 -125.3(3) . . . . ?
C2 C11 C12 C13 -121.9(3) . . . . ?
C10 C11 C12 C13 60.3(4) . . . . ?
C21 C12 C13 C14 -173.5(3) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C21 C12 C13 C18 4.7(4) . . . . ?
C11 C12 C13 C18 178.9(2) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 -176.1(3) . . . . ?
C16 C17 C18 C13 2.3(5) . . . . ?
C14 C13 C18 C17 -3.0(4) . . . . ?
C12 C13 C18 C17 178.7(3) . . . . ?
C14 C13 C18 C19 175.4(3) . . . . ?
C12 C13 C18 C19 -2.9(4) . . . . ?
C17 C18 C19 C20 177.9(3) . . . . ?
C13 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 2.0(4) . . . . ?
C13 C12 C21 C20 -3.2(4) . . . . ?
C11 C12 C21 C20 -177.7(2) . . . . ?
C13 C12 C21 C22 174.9(2) . . . . ?
C11 C12 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C12 -0.2(4) . . . . ?
C19 C20 C21 C22 -178.2(3) . . . . ?
C23 N1 C22 C21 -171.6(2) . . . . ?
C1 N1 C22 C21 49.1(3) . . . . ?
C12 C21 C22 N1 -78.4(3) . . . . ?
C20 C21 C22 N1 99.7(3) . . . . ?
C22 N1 C23 C24 160.3(2) . . . . ?
C1 N1 C23 C24 -62.0(3) . . . . ?
C22 N1 C23 C27 -80.2(3) . . . . ?
C1 N1 C23 C27 57.4(3) . . . . ?
C22 N1 C23 C29 40.0(3) . . . . ?
C1 N1 C23 C29 177.7(2) . . . . ?
N1 C23 C24 C25 -45.1(3) . . . . ?
C27 C23 C24 C25 -166.4(3) . . . . ?
C29 C23 C24 C25 74.3(3) . . . . ?
C23 C24 C25 C26 125.1(4) . . . . ?
C28 O2 C27 O1 2.3(4) . . . . ?
C28 O2 C27 C23 -173.8(2) . . . . ?
N1 C23 C27 O1 -112.6(3) . . . . ?
C24 C23 C27 O1 7.2(4) . . . . ?
C29 C23 C27 O1 127.3(3) . . . . ?
N1 C23 C27 O2 63.5(3) . . . . ?
C24 C23 C27 O2 -176.8(2) . . . . ?
C29 C23 C27 O2 -56.7(3) . . . . ?
N1 C23 C29 C30 173.8(2) . . . . ?
C24 C23 C29 C30 54.4(3) . . . . ?
C27 C23 C29 C30 -64.6(3) . . . . ?
C23 C29 C30 C31 85.1(3) . . . . ?
C23 C29 C30 C35 -99.6(3) . . . . ?
C35 C30 C31 C32 1.3(5) . . . . ?
C29 C30 C31 C32 176.7(3) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C31 C32 C33 Br 179.8(3) . . . . ?
C32 C33 C34 C35 0.0(5) . . . . ?
Br C33 C34 C35 179.8(3) . . . . ?
C33 C34 C35 C30 1.1(5) . . . . ?
C31 C30 C35 C34 -1.7(5) . . . . ?
C29 C30 C35 C34 -177.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.064






data_cd29453
_database_code_depnum_ccdc_archive 'CCDC 865415'
#TrackingRef '9387_web_deposit_cif_file_1_Ting-ShunZhu_1328158437.4k-cd29453.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H30 Br N O2'
_chemical_formula_weight         576.51

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3964(10)
_cell_length_b                   11.1200(12)
_cell_length_c                   14.1931(16)
_cell_angle_alpha                80.855(2)
_cell_angle_beta                 76.993(2)
_cell_angle_gamma                80.832(2)
_cell_volume                     1414.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2416
_cell_measurement_theta_min      4.486
_cell_measurement_theta_max      48.271

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3557
_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            7500
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5205
_reflns_number_gt                3259
_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 w=1/[\s^2^(Fo^2^)+(0.0760P)^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     SHELXL
_refine_ls_extinction_coef       0.0142(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5205
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.901
_refine_ls_shift/su_max          0.008
_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 0.58000(5) -0.01014(3) -0.36835(3) 0.0880(2) Uani 1 1 d . . .
N1 N 0.2196(2) 0.3670(2) 0.12095(16) 0.0453(6) Uani 1 1 d . . .
O1 O 0.2161(3) 0.0625(2) 0.1225(2) 0.0809(8) Uani 1 1 d . . .
O2 O 0.0469(2) 0.20163(18) 0.06804(15) 0.0563(5) Uani 1 1 d . . .
C1 C 0.1996(3) 0.3301(3) 0.2282(2) 0.0503(7) Uani 1 1 d . . .
H1A H 0.2365 0.3899 0.2561 0.060 Uiso 1 1 calc R . .
H1B H 0.2590 0.2516 0.2400 0.060 Uiso 1 1 calc R . .
C2 C 0.0433(3) 0.3190(2) 0.28032(19) 0.0481(7) Uani 1 1 d . . .
C3 C -0.0013(4) 0.2019(3) 0.3194(2) 0.0616(9) Uani 1 1 d . . .
H3 H 0.0673 0.1319 0.3132 0.074 Uiso 1 1 calc R . .
C4 C -0.1416(4) 0.1907(3) 0.3655(2) 0.0669(10) Uani 1 1 d . . .
H4 H -0.1667 0.1135 0.3935 0.080 Uiso 1 1 calc R . .
C5 C -0.2504(4) 0.2925(3) 0.3721(2) 0.0575(8) Uani 1 1 d . . .
C6 C -0.3987(5) 0.2814(4) 0.4143(3) 0.0811(11) Uani 1 1 d . . .
H6 H -0.4258 0.2048 0.4424 0.097 Uiso 1 1 calc R . .
C7 C -0.5031(5) 0.3810(5) 0.4145(3) 0.0887(12) Uani 1 1 d . . .
H7 H -0.6006 0.3720 0.4437 0.106 Uiso 1 1 calc R . .
C8 C -0.4660(4) 0.4969(4) 0.3715(3) 0.0760(10) Uani 1 1 d . . .
H8 H -0.5392 0.5637 0.3698 0.091 Uiso 1 1 calc R . .
C9 C -0.3231(3) 0.5122(3) 0.3322(2) 0.0574(8) Uani 1 1 d . . .
H9 H -0.2993 0.5901 0.3052 0.069 Uiso 1 1 calc R . .
C10 C -0.2098(3) 0.4112(3) 0.33191(19) 0.0496(7) Uani 1 1 d . . .
C11 C -0.0594(3) 0.4221(2) 0.29048(19) 0.0424(7) Uani 1 1 d . . .
C12 C -0.0066(3) 0.5448(2) 0.25274(19) 0.0412(6) Uani 1 1 d . . .
C13 C -0.0225(3) 0.6384(2) 0.3135(2) 0.0448(7) Uani 1 1 d . . .
C14 C -0.0872(3) 0.6241(3) 0.4141(2) 0.0548(8) Uani 1 1 d . . .
H14 H -0.1219 0.5504 0.4430 0.066 Uiso 1 1 calc R . .
C15 C -0.0996(4) 0.7161(3) 0.4692(2) 0.0692(9) Uani 1 1 d . . .
H15 H -0.1419 0.7041 0.5353 0.083 Uiso 1 1 calc R . .
C16 C -0.0499(4) 0.8283(3) 0.4281(3) 0.0735(10) Uani 1 1 d . . .
H16 H -0.0608 0.8913 0.4662 0.088 Uiso 1 1 calc R . .
C17 C 0.0145(4) 0.8445(3) 0.3322(3) 0.0635(9) Uani 1 1 d . . .
H17 H 0.0475 0.9194 0.3050 0.076 Uiso 1 1 calc R . .
C18 C 0.0330(3) 0.7513(2) 0.2725(2) 0.0483(7) Uani 1 1 d . . .
C19 C 0.1075(3) 0.7647(3) 0.1744(2) 0.0526(8) Uani 1 1 d . . .
H19 H 0.1436 0.8383 0.1468 0.063 Uiso 1 1 calc R . .
C20 C 0.1275(3) 0.6719(3) 0.1197(2) 0.0512(7) Uani 1 1 d . . .
H20 H 0.1797 0.6820 0.0557 0.061 Uiso 1 1 calc R . .
C21 C 0.0707(3) 0.5604(2) 0.1578(2) 0.0422(6) Uani 1 1 d . . .
C22 C 0.0986(3) 0.4578(2) 0.0959(2) 0.0461(7) Uani 1 1 d . . .
H22A H 0.0102 0.4187 0.1062 0.055 Uiso 1 1 calc R . .
H22B H 0.1232 0.4907 0.0276 0.055 Uiso 1 1 calc R . .
C23 C 0.2789(3) 0.2675(2) 0.0598(2) 0.0462(7) Uani 1 1 d . . .
C24 C 0.4330(3) 0.2140(3) 0.0769(2) 0.0519(7) Uani 1 1 d . . .
H24A H 0.4237 0.1619 0.1390 0.062 Uiso 1 1 calc R . .
H24B H 0.4814 0.1633 0.0264 0.062 Uiso 1 1 calc R . .
C25 C 0.5271(3) 0.3111(3) 0.0769(2) 0.0607(8) Uani 1 1 d . . .
H25 H 0.5398 0.3704 0.0226 0.073 Uiso 1 1 calc R . .
C26 C 0.5922(4) 0.3182(4) 0.1469(3) 0.0772(10) Uani 1 1 d . . .
H26A H 0.5820 0.2604 0.2023 0.093 Uiso 1 1 calc R . .
H26B H 0.6490 0.3812 0.1418 0.093 Uiso 1 1 calc R . .
C27 C 0.1809(3) 0.1635(3) 0.0858(2) 0.0490(7) Uani 1 1 d . . .
C28 C -0.0599(4) 0.1162(3) 0.0985(3) 0.0672(9) Uani 1 1 d . . .
H28A H -0.0283 0.0468 0.0629 0.101 Uiso 1 1 calc R . .
H28B H -0.1535 0.1558 0.0860 0.101 Uiso 1 1 calc R . .
H28C H -0.0690 0.0889 0.1671 0.101 Uiso 1 1 calc R . .
C29 C 0.2864(3) 0.3213(3) -0.0491(2) 0.0470(7) Uani 1 1 d . . .
H29A H 0.1866 0.3495 -0.0581 0.056 Uiso 1 1 calc R . .
H29B H 0.3385 0.3927 -0.0623 0.056 Uiso 1 1 calc R . .
C30 C 0.3591(3) 0.2365(2) -0.1240(2) 0.0441(7) Uani 1 1 d . . .
C31 C 0.2831(4) 0.1573(3) -0.1516(2) 0.0644(9) Uani 1 1 d . . .
H31 H 0.1853 0.1528 -0.1207 0.077 Uiso 1 1 calc R . .
C32 C 0.3466(4) 0.0838(3) -0.2236(3) 0.0725(10) Uani 1 1 d . . .
H32 H 0.2926 0.0305 -0.2406 0.087 Uiso 1 1 calc R . .
C33 C 0.4892(4) 0.0904(3) -0.2691(2) 0.0560(8) Uani 1 1 d . . .
C34 C 0.5682(4) 0.1691(3) -0.2444(2) 0.0651(9) Uani 1 1 d . . .
H34 H 0.6658 0.1734 -0.2757 0.078 Uiso 1 1 calc R . .
C35 C 0.5024(3) 0.2420(3) -0.1729(2) 0.0626(9) Uani 1 1 d . . .
H35 H 0.5562 0.2965 -0.1572 0.075 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 0.1244(4) 0.0731(3) 0.0657(3) -0.0284(2) -0.0071(2) -0.0080(2)
N1 0.0540(14) 0.0392(13) 0.0410(13) -0.0011(10) -0.0125(11) -0.0010(11)
O1 0.0782(16) 0.0438(13) 0.122(2) 0.0168(14) -0.0378(15) -0.0131(12)
O2 0.0474(12) 0.0524(12) 0.0677(14) 0.0029(10) -0.0124(10) -0.0126(10)
C1 0.064(2) 0.0430(16) 0.0441(16) -0.0018(13) -0.0191(15) -0.0007(14)
C2 0.073(2) 0.0390(16) 0.0344(15) -0.0009(12) -0.0143(14) -0.0121(15)
C3 0.098(3) 0.0394(17) 0.0472(18) -0.0033(14) -0.0140(18) -0.0101(17)
C4 0.109(3) 0.048(2) 0.0474(19) 0.0016(15) -0.0119(19) -0.036(2)
C5 0.080(2) 0.058(2) 0.0396(17) -0.0067(14) -0.0032(15) -0.0341(18)
C6 0.101(3) 0.087(3) 0.061(2) -0.012(2) 0.005(2) -0.055(3)
C7 0.072(3) 0.120(4) 0.076(3) -0.024(3) 0.015(2) -0.050(3)
C8 0.061(2) 0.091(3) 0.075(2) -0.021(2) 0.0027(18) -0.019(2)
C9 0.058(2) 0.064(2) 0.0509(18) -0.0118(15) -0.0026(15) -0.0196(17)
C10 0.065(2) 0.0499(18) 0.0370(15) -0.0080(13) -0.0052(14) -0.0219(16)
C11 0.0570(18) 0.0381(15) 0.0347(14) -0.0018(12) -0.0103(13) -0.0158(13)
C12 0.0445(16) 0.0358(15) 0.0447(16) -0.0008(12) -0.0115(13) -0.0100(12)
C13 0.0485(17) 0.0391(15) 0.0476(16) -0.0011(13) -0.0122(13) -0.0095(13)
C14 0.070(2) 0.0483(17) 0.0485(18) -0.0079(14) -0.0108(15) -0.0158(15)
C15 0.095(3) 0.068(2) 0.0500(19) -0.0148(17) -0.0174(18) -0.0163(19)
C16 0.102(3) 0.054(2) 0.076(3) -0.0249(19) -0.028(2) -0.0126(19)
C17 0.078(2) 0.0388(17) 0.080(3) -0.0092(17) -0.0240(19) -0.0133(16)
C18 0.0488(17) 0.0377(16) 0.0603(19) -0.0008(14) -0.0162(15) -0.0093(13)
C19 0.0545(18) 0.0358(16) 0.065(2) 0.0067(15) -0.0095(15) -0.0150(13)
C20 0.0476(17) 0.0465(17) 0.0534(18) 0.0048(15) -0.0049(14) -0.0073(14)
C21 0.0409(16) 0.0398(15) 0.0434(15) 0.0021(12) -0.0100(12) -0.0031(12)
C22 0.0529(17) 0.0432(16) 0.0402(15) -0.0003(13) -0.0109(13) -0.0030(13)
C23 0.0505(17) 0.0428(16) 0.0443(16) -0.0026(13) -0.0098(13) -0.0061(13)
C24 0.0523(18) 0.0522(17) 0.0500(17) -0.0073(14) -0.0127(14) 0.0005(14)
C25 0.0487(18) 0.070(2) 0.061(2) -0.0019(17) -0.0125(16) -0.0060(16)
C26 0.071(2) 0.090(3) 0.078(3) -0.021(2) -0.017(2) -0.019(2)
C27 0.0512(19) 0.0463(18) 0.0491(17) -0.0055(14) -0.0112(14) -0.0043(14)
C28 0.064(2) 0.067(2) 0.075(2) -0.0051(18) -0.0132(17) -0.0272(17)
C29 0.0481(17) 0.0454(16) 0.0472(17) -0.0042(13) -0.0098(13) -0.0071(13)
C30 0.0445(17) 0.0454(16) 0.0429(16) -0.0015(13) -0.0125(13) -0.0064(13)
C31 0.0526(19) 0.082(2) 0.063(2) -0.0215(18) -0.0034(16) -0.0233(17)
C32 0.085(3) 0.077(2) 0.067(2) -0.0219(19) -0.0092(19) -0.041(2)
C33 0.071(2) 0.0505(18) 0.0462(17) -0.0053(14) -0.0143(16) -0.0034(16)
C34 0.0497(19) 0.085(2) 0.066(2) -0.0319(19) -0.0028(16) -0.0150(17)
C35 0.056(2) 0.074(2) 0.067(2) -0.0270(18) -0.0086(16) -0.0227(16)

_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 C33 1.901(3) . ?
N1 C22 1.463(3) . ?
N1 C23 1.475(3) . ?
N1 C1 1.489(3) . ?
O1 C27 1.189(3) . ?
O2 C27 1.330(3) . ?
O2 C28 1.441(3) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C11 1.379(4) . ?
C2 C3 1.421(4) . ?
C3 C4 1.349(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(5) . ?
C5 C10 1.427(4) . ?
C6 C7 1.357(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(4) . ?
C11 C12 1.503(4) . ?
C12 C21 1.377(4) . ?
C12 C13 1.424(4) . ?
C13 C14 1.414(4) . ?
C13 C18 1.424(4) . ?
C14 C15 1.360(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.357(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.406(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.407(4) . ?
C19 C20 1.353(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.503(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.533(4) . ?
C23 C27 1.540(4) . ?
C23 C29 1.556(4) . ?
C24 C25 1.500(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.298(5) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9300 . ?
C26 H26B 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.508(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.369(4) . ?
C30 C35 1.375(4) . ?
C31 C32 1.379(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.358(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.365(4) . ?
C34 C35 1.374(4) . ?
C34 H34 0.9300 . ?
C35 H35 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
C22 N1 C23 119.1(2) . . ?
C22 N1 C1 111.6(2) . . ?
C23 N1 C1 115.9(2) . . ?
C27 O2 C28 117.2(2) . . ?
N1 C1 C2 114.9(2) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C11 C2 C3 118.9(3) . . ?
C11 C2 C1 120.7(2) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 C10 118.8(3) . . ?
C6 C5 C10 118.9(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 123.2(3) . . ?
C9 C10 C5 118.1(3) . . ?
C11 C10 C5 118.7(3) . . ?
C2 C11 C10 120.8(2) . . ?
C2 C11 C12 117.4(2) . . ?
C10 C11 C12 121.8(2) . . ?
C21 C12 C13 120.2(2) . . ?
C21 C12 C11 117.2(2) . . ?
C13 C12 C11 122.4(2) . . ?
C14 C13 C12 123.4(2) . . ?
C14 C13 C18 117.7(3) . . ?
C12 C13 C18 118.9(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 122.3(3) . . ?
C17 C18 C13 118.8(3) . . ?
C19 C18 C13 118.9(3) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C12 C21 C20 119.6(3) . . ?
C12 C21 C22 120.4(2) . . ?
C20 C21 C22 120.0(3) . . ?
N1 C22 C21 110.3(2) . . ?
N1 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
N1 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
N1 C23 C24 108.9(2) . . ?
N1 C23 C27 111.3(2) . . ?
C24 C23 C27 108.4(2) . . ?
N1 C23 C29 108.9(2) . . ?
C24 C23 C29 110.3(2) . . ?
C27 C23 C29 109.0(2) . . ?
C25 C24 C23 112.9(2) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 124.8(3) . . ?
C26 C25 H25 117.6 . . ?
C24 C25 H25 117.6 . . ?
C25 C26 H26A 120.0 . . ?
C25 C26 H26B 120.0 . . ?
H26A C26 H26B 120.0 . . ?
O1 C27 O2 123.1(3) . . ?
O1 C27 C23 124.9(3) . . ?
O2 C27 C23 111.9(2) . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C23 116.9(2) . . ?
C30 C29 H29A 108.1 . . ?
C23 C29 H29A 108.1 . . ?
C30 C29 H29B 108.1 . . ?
C23 C29 H29B 108.1 . . ?
H29A C29 H29B 107.3 . . ?
C31 C30 C35 117.0(3) . . ?
C31 C30 C29 121.8(3) . . ?
C35 C30 C29 121.1(3) . . ?
C30 C31 C32 122.2(3) . . ?
C30 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
C33 C32 C31 119.1(3) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 120.4(3) . . ?
C32 C33 Br 120.1(3) . . ?
C34 C33 Br 119.5(3) . . ?
C33 C34 C35 119.5(3) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C34 C35 C30 121.8(3) . . ?
C34 C35 H35 119.1 . . ?
C30 C35 H35 119.1 . . ?

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
C22 N1 C1 C2 37.9(3) . . . . ?
C23 N1 C1 C2 -102.9(3) . . . . ?
N1 C1 C2 C11 -69.9(3) . . . . ?
N1 C1 C2 C3 109.6(3) . . . . ?
C11 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 3.4(5) . . . . ?
C3 C4 C5 C6 175.8(3) . . . . ?
C3 C4 C5 C10 -2.1(5) . . . . ?
C4 C5 C6 C7 -176.1(4) . . . . ?
C10 C5 C6 C7 1.9(5) . . . . ?
C5 C6 C7 C8 1.0(6) . . . . ?
C6 C7 C8 C9 -2.7(6) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C8 C9 C10 C11 179.0(3) . . . . ?
C8 C9 C10 C5 1.3(4) . . . . ?
C4 C5 C10 C9 175.1(3) . . . . ?
C6 C5 C10 C9 -3.0(4) . . . . ?
C4 C5 C10 C11 -2.7(4) . . . . ?
C6 C5 C10 C11 179.2(3) . . . . ?
C3 C2 C11 C10 -5.2(4) . . . . ?
C1 C2 C11 C10 174.3(3) . . . . ?
C3 C2 C11 C12 176.9(3) . . . . ?
C1 C2 C11 C12 -3.5(4) . . . . ?
C9 C10 C11 C2 -171.2(3) . . . . ?
C5 C10 C11 C2 6.4(4) . . . . ?
C9 C10 C11 C12 6.5(4) . . . . ?
C5 C10 C11 C12 -175.8(3) . . . . ?
C2 C11 C12 C21 52.5(3) . . . . ?
C10 C11 C12 C21 -125.3(3) . . . . ?
C2 C11 C12 C13 -121.9(3) . . . . ?
C10 C11 C12 C13 60.3(4) . . . . ?
C21 C12 C13 C14 -173.5(3) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C21 C12 C13 C18 4.7(4) . . . . ?
C11 C12 C13 C18 178.9(2) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C17 -1.4(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 -176.1(3) . . . . ?
C16 C17 C18 C13 2.3(5) . . . . ?
C14 C13 C18 C17 -3.0(4) . . . . ?
C12 C13 C18 C17 178.7(3) . . . . ?
C14 C13 C18 C19 175.4(3) . . . . ?
C12 C13 C18 C19 -2.9(4) . . . . ?
C17 C18 C19 C20 177.9(3) . . . . ?
C13 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 2.0(4) . . . . ?
C13 C12 C21 C20 -3.2(4) . . . . ?
C11 C12 C21 C20 -177.7(2) . . . . ?
C13 C12 C21 C22 174.9(2) . . . . ?
C11 C12 C21 C22 0.4(4) . . . . ?
C19 C20 C21 C12 -0.2(4) . . . . ?
C19 C20 C21 C22 -178.2(3) . . . . ?
C23 N1 C22 C21 -171.6(2) . . . . ?
C1 N1 C22 C21 49.1(3) . . . . ?
C12 C21 C22 N1 -78.4(3) . . . . ?
C20 C21 C22 N1 99.7(3) . . . . ?
C22 N1 C23 C24 160.3(2) . . . . ?
C1 N1 C23 C24 -62.0(3) . . . . ?
C22 N1 C23 C27 -80.2(3) . . . . ?
C1 N1 C23 C27 57.4(3) . . . . ?
C22 N1 C23 C29 40.0(3) . . . . ?
C1 N1 C23 C29 177.7(2) . . . . ?
N1 C23 C24 C25 -45.1(3) . . . . ?
C27 C23 C24 C25 -166.4(3) . . . . ?
C29 C23 C24 C25 74.3(3) . . . . ?
C23 C24 C25 C26 125.1(4) . . . . ?
C28 O2 C27 O1 2.3(4) . . . . ?
C28 O2 C27 C23 -173.8(2) . . . . ?
N1 C23 C27 O1 -112.6(3) . . . . ?
C24 C23 C27 O1 7.2(4) . . . . ?
C29 C23 C27 O1 127.3(3) . . . . ?
N1 C23 C27 O2 63.5(3) . . . . ?
C24 C23 C27 O2 -176.8(2) . . . . ?
C29 C23 C27 O2 -56.7(3) . . . . ?
N1 C23 C29 C30 173.8(2) . . . . ?
C24 C23 C29 C30 54.4(3) . . . . ?
C27 C23 C29 C30 -64.6(3) . . . . ?
C23 C29 C30 C31 85.1(3) . . . . ?
C23 C29 C30 C35 -99.6(3) . . . . ?
C35 C30 C31 C32 1.3(5) . . . . ?
C29 C30 C31 C32 176.7(3) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C31 C32 C33 C34 -0.4(5) . . . . ?
C31 C32 C33 Br 179.8(3) . . . . ?
C32 C33 C34 C35 0.0(5) . . . . ?
Br C33 C34 C35 179.8(3) . . . . ?
C33 C34 C35 C30 1.1(5) . . . . ?
C31 C30 C35 C34 -1.7(5) . . . . ?
C29 C30 C35 C34 -177.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.064