# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_cheny21
_database_code_depnum_ccdc_archive 'CCDC 812056'
#TrackingRef 'CHENY21.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Br N O'
_chemical_formula_weight         394.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_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                   5.7061(5)
_cell_length_b                   17.0480(15)
_cell_length_c                   18.4614(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1795.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    100
_cell_measurement_theta_min      5
_cell_measurement_theta_max      85

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    3.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            10032
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         65.94
_reflns_number_total             2984
_reflns_number_gt                2936
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0374P)^2^+0.5036P] 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   0.004(15)
_refine_ls_number_reflns         2984
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
Br1 Br 1.00758(4) 0.715336(11) 0.666051(10) 0.02731(9) Uani 1 1 d . . .
O1 O 0.4097(2) 0.09888(8) 0.43471(7) 0.0190(3) Uani 1 1 d . . .
N1 N 0.8193(3) 0.40603(10) 0.29892(9) 0.0196(4) Uani 1 1 d . . .
H1A H 0.8667 0.3603 0.2824 0.024 Uiso 1 1 calc R . .
C1 C 0.9437(3) 0.47336(12) 0.28166(10) 0.0181(4) Uani 1 1 d . . .
C2 C 1.1094(4) 0.47076(13) 0.22522(11) 0.0218(4) Uani 1 1 d . . .
H2A H 1.1306 0.4233 0.1990 0.026 Uiso 1 1 calc R . .
C3 C 1.2412(4) 0.53527(14) 0.20724(11) 0.0252(5) Uani 1 1 d . . .
H3A H 1.3522 0.5321 0.1690 0.030 Uiso 1 1 calc R . .
C4 C 1.2123(4) 0.60523(14) 0.24490(11) 0.0264(5) Uani 1 1 d . . .
H4A H 1.3021 0.6502 0.2325 0.032 Uiso 1 1 calc R . .
C5 C 1.0503(4) 0.60839(13) 0.30100(11) 0.0245(5) Uani 1 1 d . . .
H5A H 1.0312 0.6561 0.3269 0.029 Uiso 1 1 calc R . .
C6 C 0.9145(3) 0.54339(12) 0.32040(10) 0.0181(4) Uani 1 1 d . . .
C7 C 0.7323(4) 0.54868(12) 0.38055(11) 0.0183(4) Uani 1 1 d . . .
H7A H 0.5893 0.5744 0.3602 0.022 Uiso 1 1 calc R . .
C8 C 0.8104(4) 0.59560(11) 0.44613(11) 0.0176(4) Uani 1 1 d . . .
C9 C 1.0247(4) 0.58031(11) 0.47958(10) 0.0204(4) Uani 1 1 d . . .
H9A H 1.1315 0.5448 0.4575 0.025 Uiso 1 1 calc R . .
C10 C 1.0849(4) 0.61613(12) 0.54468(10) 0.0202(4) Uani 1 1 d . . .
H10A H 1.2309 0.6053 0.5672 0.024 Uiso 1 1 calc R . .
C11 C 0.9285(4) 0.66765(11) 0.57581(10) 0.0201(4) Uani 1 1 d . . .
C12 C 0.7159(4) 0.68537(12) 0.54382(11) 0.0216(4) Uani 1 1 d . . .
H12A H 0.6114 0.7218 0.5656 0.026 Uiso 1 1 calc R . .
C13 C 0.6589(4) 0.64866(12) 0.47898(11) 0.0199(4) Uani 1 1 d . . .
H13A H 0.5130 0.6601 0.4566 0.024 Uiso 1 1 calc R . .
C14 C 0.6625(3) 0.46605(12) 0.40672(10) 0.0182(4) Uani 1 1 d . . .
H14A H 0.7917 0.4440 0.4362 0.022 Uiso 1 1 calc R . .
H14B H 0.5225 0.4702 0.4381 0.022 Uiso 1 1 calc R . .
C15 C 0.6095(4) 0.41042(12) 0.34446(10) 0.0179(4) Uani 1 1 d . . .
H15A H 0.4766 0.4319 0.3153 0.021 Uiso 1 1 calc R . .
C16 C 0.5482(3) 0.32873(11) 0.36985(10) 0.0166(4) Uani 1 1 d . . .
C17 C 0.3386(4) 0.29313(12) 0.34926(11) 0.0184(4) Uani 1 1 d . . .
H17A H 0.2296 0.3218 0.3208 0.022 Uiso 1 1 calc R . .
C18 C 0.2854(3) 0.21661(12) 0.36942(11) 0.0190(4) Uani 1 1 d . . .
H18A H 0.1433 0.1929 0.3539 0.023 Uiso 1 1 calc R . .
C19 C 0.4423(3) 0.17500(11) 0.41257(10) 0.0160(4) Uani 1 1 d . . .
C20 C 0.6495(3) 0.21036(12) 0.43581(10) 0.0184(4) Uani 1 1 d . . .
H20A H 0.7542 0.1826 0.4665 0.022 Uiso 1 1 calc R . .
C21 C 0.7022(3) 0.28612(12) 0.41399(10) 0.0188(4) Uani 1 1 d . . .
H21A H 0.8450 0.3095 0.4292 0.023 Uiso 1 1 calc R . .
C22 C 0.2125(4) 0.05884(12) 0.40403(12) 0.0222(4) Uani 1 1 d . . .
H22A H 0.2158 0.0036 0.4187 0.033 Uiso 1 1 calc R . .
H22B H 0.2194 0.0623 0.3511 0.033 Uiso 1 1 calc R . .
H22C H 0.0673 0.0832 0.4213 0.033 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
Br1 0.03955(15) 0.02417(13) 0.01822(13) -0.00176(7) -0.00058(11) -0.00105(12)
O1 0.0218(7) 0.0170(7) 0.0182(6) 0.0013(5) -0.0016(6) -0.0022(5)
N1 0.0240(9) 0.0164(8) 0.0184(8) -0.0007(7) 0.0042(7) 0.0001(7)
C1 0.0162(10) 0.0221(10) 0.0161(9) 0.0040(7) -0.0030(8) 0.0021(8)
C2 0.0215(10) 0.0267(11) 0.0172(10) 0.0022(8) -0.0005(9) 0.0039(9)
C3 0.0187(10) 0.0401(13) 0.0169(10) 0.0049(9) -0.0002(8) 0.0003(10)
C4 0.0269(12) 0.0312(12) 0.0211(11) 0.0066(9) -0.0017(9) -0.0111(10)
C5 0.0274(13) 0.0262(11) 0.0199(10) 0.0030(8) -0.0022(9) -0.0058(9)
C6 0.0184(9) 0.0214(10) 0.0145(9) 0.0019(8) -0.0034(8) 0.0002(8)
C7 0.0182(10) 0.0188(10) 0.0178(10) 0.0022(8) -0.0004(9) 0.0004(8)
C8 0.0213(10) 0.0142(9) 0.0172(10) 0.0035(8) 0.0013(8) -0.0023(8)
C9 0.0198(10) 0.0205(9) 0.0211(9) -0.0006(7) 0.0021(9) 0.0004(9)
C10 0.0199(10) 0.0218(10) 0.0188(10) 0.0030(8) -0.0015(8) -0.0035(8)
C11 0.0281(11) 0.0164(9) 0.0158(9) 0.0015(8) 0.0009(8) -0.0055(8)
C12 0.0255(11) 0.0155(10) 0.0237(10) 0.0006(8) 0.0057(9) 0.0026(8)
C13 0.0194(10) 0.0184(9) 0.0220(10) 0.0043(8) 0.0006(8) 0.0013(8)
C14 0.0182(9) 0.0194(10) 0.0169(9) 0.0002(8) 0.0025(8) 0.0001(9)
C15 0.0173(9) 0.0192(10) 0.0172(9) 0.0014(8) -0.0024(8) 0.0003(8)
C16 0.0192(10) 0.0176(9) 0.0132(8) -0.0006(7) 0.0014(8) -0.0005(8)
C17 0.0161(9) 0.0228(10) 0.0162(9) 0.0023(8) -0.0019(7) 0.0017(9)
C18 0.0160(9) 0.0228(10) 0.0183(10) -0.0025(8) -0.0003(8) -0.0013(9)
C19 0.0182(10) 0.0174(9) 0.0123(8) -0.0011(7) 0.0029(7) 0.0013(8)
C20 0.0187(9) 0.0216(10) 0.0148(9) 0.0005(8) -0.0011(8) 0.0019(9)
C21 0.0169(9) 0.0220(10) 0.0176(9) -0.0024(8) -0.0003(8) 0.0004(9)
C22 0.0222(11) 0.0194(10) 0.0251(11) -0.0007(8) -0.0014(9) -0.0044(9)

_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
Br1 C11 1.908(2) . ?
O1 C19 1.373(2) . ?
O1 C22 1.433(3) . ?
N1 C1 1.387(3) . ?
N1 C15 1.464(3) . ?
C1 C6 1.402(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.524(3) . ?
C7 C8 1.518(3) . ?
C7 C14 1.542(3) . ?
C8 C13 1.390(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.391(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.389(3) . ?
C14 C15 1.520(3) . ?
C15 C16 1.511(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.401(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.393(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.386(3) . ?

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
C19 O1 C22 116.05(15) . . ?
C1 N1 C15 120.53(16) . . ?
N1 C1 C6 121.79(17) . . ?
N1 C1 C2 119.20(18) . . ?
C6 C1 C2 118.97(19) . . ?
C3 C2 C1 121.4(2) . . ?
C2 C3 C4 120.1(2) . . ?
C5 C4 C3 119.0(2) . . ?
C4 C5 C6 121.9(2) . . ?
C5 C6 C1 118.57(18) . . ?
C5 C6 C7 121.17(18) . . ?
C1 C6 C7 120.23(18) . . ?
C8 C7 C6 114.33(17) . . ?
C8 C7 C14 107.91(15) . . ?
C6 C7 C14 110.51(16) . . ?
C13 C8 C9 118.28(18) . . ?
C13 C8 C7 120.53(18) . . ?
C9 C8 C7 120.81(18) . . ?
C10 C9 C8 121.12(19) . . ?
C11 C10 C9 118.73(19) . . ?
C10 C11 C12 121.95(19) . . ?
C10 C11 Br1 118.88(15) . . ?
C12 C11 Br1 119.17(15) . . ?
C11 C12 C13 118.37(19) . . ?
C12 C13 C8 121.55(19) . . ?
C15 C14 C7 112.61(16) . . ?
N1 C15 C16 108.69(16) . . ?
N1 C15 C14 107.66(16) . . ?
C16 C15 C14 112.74(16) . . ?
C17 C16 C21 118.09(18) . . ?
C17 C16 C15 121.05(18) . . ?
C21 C16 C15 120.85(18) . . ?
C18 C17 C16 121.54(19) . . ?
C17 C18 C19 119.38(18) . . ?
O1 C19 C18 124.35(18) . . ?
O1 C19 C20 115.60(17) . . ?
C18 C19 C20 120.05(18) . . ?
C21 C20 C19 119.83(18) . . ?
C20 C21 C16 121.05(18) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        65.94
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.052


data_cheny26
_database_code_depnum_ccdc_archive 'CCDC 812057'
#TrackingRef 'CHENY26.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Br N O'
_chemical_formula_weight         330.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   8.4384(3)
_cell_length_b                   5.3564(2)
_cell_length_c                   16.3563(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.619(2)
_cell_angle_gamma                90.00
_cell_volume                     737.82(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    112
_cell_measurement_theta_min      4
_cell_measurement_theta_max      85

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            8916
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         65.65
_reflns_number_total             2324
_reflns_number_gt                1836
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0591P)^2^+0.1621P] 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   0.04(4)
_refine_ls_number_reflns         2324
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.28003(7) 0.46862(19) -0.11814(3) 0.0950(3) Uani 1 1 d . . .
O1 O 0.5187(5) 0.3324(7) 0.3605(4) 0.0824(13) Uani 1 1 d . . .
N1 N 0.2255(4) 0.9288(9) 0.2170(3) 0.0715(11) Uani 1 1 d . . .
H1A H 0.1838 1.0747 0.2205 0.086 Uiso 1 1 calc R . .
C1 C 0.2415(5) 0.8266(9) 0.1407(4) 0.0618(13) Uani 1 1 d . . .
C2 C 0.1650(5) 0.9349(12) 0.0703(4) 0.0716(14) Uani 1 1 d . . .
H2A H 0.1048 1.0787 0.0757 0.086 Uiso 1 1 calc R . .
C3 C 0.1775(6) 0.8330(10) -0.0060(4) 0.0725(15) Uani 1 1 d . . .
H3A H 0.1256 0.9057 -0.0519 0.087 Uiso 1 1 calc R . .
C4 C 0.2674(5) 0.6226(10) -0.0135(3) 0.0683(14) Uani 1 1 d . . .
C5 C 0.3488(5) 0.5130(10) 0.0535(3) 0.0629(13) Uani 1 1 d . . .
H5A H 0.4116 0.3728 0.0467 0.075 Uiso 1 1 calc R . .
C6 C 0.3354(5) 0.6146(9) 0.1307(3) 0.0576(11) Uani 1 1 d . . .
C7 C 0.4246(5) 0.5019(9) 0.2047(3) 0.0616(12) Uani 1 1 d . . .
H7A H 0.5296 0.4521 0.1898 0.074 Uiso 1 1 calc R . .
H7B H 0.3694 0.3531 0.2211 0.074 Uiso 1 1 calc R . .
C8 C 0.4412(5) 0.6801(8) 0.2764(3) 0.0596(12) Uani 1 1 d . . .
H8A H 0.5117 0.8156 0.2612 0.072 Uiso 1 1 calc R . .
C9 C 0.2766(5) 0.7986(8) 0.2914(3) 0.0618(12) Uani 1 1 d . . .
H9A H 0.2939 0.9241 0.3346 0.074 Uiso 1 1 calc R . .
C10 C 0.1557(5) 0.6129(10) 0.3200(4) 0.0619(12) Uani 1 1 d . . .
C11 C 0.0337(5) 0.5218(10) 0.2684(3) 0.0710(15) Uani 1 1 d . . .
H11A H 0.0253 0.5737 0.2141 0.085 Uiso 1 1 calc R . .
C12 C -0.0749(7) 0.3575(12) 0.2952(5) 0.0883(19) Uani 1 1 d . . .
H12A H -0.1572 0.3011 0.2594 0.106 Uiso 1 1 calc R . .
C13 C -0.0632(7) 0.2749(13) 0.3747(5) 0.095(2) Uani 1 1 d . . .
H13A H -0.1358 0.1604 0.3931 0.114 Uiso 1 1 calc R . .
C14 C 0.0581(7) 0.3649(13) 0.4269(5) 0.093(2) Uani 1 1 d . . .
H14A H 0.0684 0.3109 0.4810 0.111 Uiso 1 1 calc R . .
C15 C 0.1634(6) 0.5340(11) 0.3988(4) 0.0798(18) Uani 1 1 d . . .
H15A H 0.2429 0.5968 0.4351 0.096 Uiso 1 1 calc R . .
C16 C 0.5171(6) 0.5574(10) 0.3534(5) 0.0643(15) Uani 1 1 d . . .
C17 C 0.5944(7) 0.7201(11) 0.4166(4) 0.0887(18) Uani 1 1 d . . .
H17A H 0.6028 0.6333 0.4680 0.133 Uiso 1 1 calc R . .
H17B H 0.5322 0.8686 0.4218 0.133 Uiso 1 1 calc R . .
H17C H 0.6985 0.7645 0.4010 0.133 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
Br1 0.0903(4) 0.1095(5) 0.0864(4) 0.0080(5) 0.0156(3) -0.0037(5)
O1 0.081(3) 0.054(3) 0.112(4) 0.010(2) -0.004(2) 0.008(2)
N1 0.071(2) 0.038(2) 0.105(3) -0.002(3) -0.001(2) 0.012(2)
C1 0.044(2) 0.043(2) 0.098(4) 0.006(3) 0.002(2) -0.003(2)
C2 0.051(2) 0.051(3) 0.112(4) 0.016(4) -0.003(2) 0.009(3)
C3 0.053(3) 0.063(3) 0.100(4) 0.026(3) -0.006(3) -0.008(2)
C4 0.046(3) 0.064(3) 0.094(4) 0.020(3) -0.001(2) -0.010(2)
C5 0.043(2) 0.056(4) 0.090(3) 0.007(3) 0.0106(19) 0.002(2)
C6 0.045(2) 0.039(2) 0.088(3) 0.005(2) 0.003(2) 0.0013(19)
C7 0.052(2) 0.043(3) 0.089(3) 0.000(3) 0.004(2) 0.008(2)
C8 0.046(2) 0.041(3) 0.092(3) 0.002(2) 0.003(2) -0.0050(19)
C9 0.056(3) 0.040(2) 0.090(4) -0.009(2) 0.002(2) -0.003(2)
C10 0.044(2) 0.052(2) 0.090(4) -0.018(3) 0.009(2) 0.006(2)
C11 0.047(2) 0.072(4) 0.094(3) -0.010(3) 0.006(2) -0.006(2)
C12 0.056(3) 0.096(5) 0.113(5) -0.027(4) 0.008(3) -0.018(3)
C13 0.066(4) 0.089(4) 0.132(6) -0.007(4) 0.023(4) -0.021(3)
C14 0.064(3) 0.105(5) 0.110(5) 0.014(3) 0.012(3) -0.014(3)
C15 0.050(3) 0.086(5) 0.104(4) -0.008(3) 0.006(3) -0.008(3)
C16 0.045(3) 0.057(4) 0.091(4) 0.001(3) -0.001(3) 0.002(2)
C17 0.086(4) 0.066(3) 0.111(5) -0.001(3) -0.023(4) -0.011(3)

_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
Br1 C4 1.908(6) . ?
O1 C16 1.211(6) . ?
N1 C1 1.378(7) . ?
N1 C9 1.445(7) . ?
C1 C6 1.400(7) . ?
C1 C2 1.409(8) . ?
C2 C3 1.372(8) . ?
C3 C4 1.368(8) . ?
C4 C5 1.387(7) . ?
C5 C6 1.387(7) . ?
C6 C7 1.510(6) . ?
C7 C8 1.512(7) . ?
C8 C16 1.526(8) . ?
C8 C9 1.561(6) . ?
C9 C10 1.520(7) . ?
C10 C15 1.354(8) . ?
C10 C11 1.379(7) . ?
C11 C12 1.362(8) . ?
C12 C13 1.372(10) . ?
C13 C14 1.378(10) . ?
C14 C15 1.368(8) . ?
C16 C17 1.472(9) . ?

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 N1 C9 122.0(4) . . ?
N1 C1 C6 121.1(5) . . ?
N1 C1 C2 120.7(5) . . ?
C6 C1 C2 118.2(6) . . ?
C3 C2 C1 121.5(5) . . ?
C4 C3 C2 119.0(5) . . ?
C3 C4 C5 121.8(6) . . ?
C3 C4 Br1 120.0(4) . . ?
C5 C4 Br1 118.2(4) . . ?
C6 C5 C4 119.3(5) . . ?
C5 C6 C1 120.2(5) . . ?
C5 C6 C7 120.5(4) . . ?
C1 C6 C7 119.3(5) . . ?
C6 C7 C8 112.7(4) . . ?
C7 C8 C16 112.5(4) . . ?
C7 C8 C9 109.8(4) . . ?
C16 C8 C9 112.1(5) . . ?
N1 C9 C10 113.9(4) . . ?
N1 C9 C8 106.5(4) . . ?
C10 C9 C8 113.8(4) . . ?
C15 C10 C11 117.5(5) . . ?
C15 C10 C9 120.3(5) . . ?
C11 C10 C9 122.2(5) . . ?
C12 C11 C10 121.5(6) . . ?
C11 C12 C13 120.3(6) . . ?
C12 C13 C14 118.7(6) . . ?
C15 C14 C13 119.8(7) . . ?
C10 C15 C14 122.2(6) . . ?
O1 C16 C17 121.4(8) . . ?
O1 C16 C8 120.6(7) . . ?
C17 C16 C8 118.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        65.65
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.053