# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd21218

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   7.2969(11)
_cell_length_b                   11.1694(16)
_cell_length_c                   16.483(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1343.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1605
_cell_measurement_theta_min      4.405
_cell_measurement_theta_max      43.679

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    3.054
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.51956
_exptl_absorpt_correction_T_max  1.00000
_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            7736
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2627
_reflns_number_gt                1955
_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^)+(0.0643P)^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   0.026(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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 1.08825(8) 0.32898(5) -0.04654(3) 0.0811(2) Uani 1 1 d . . .
O1 O 0.8383(5) 0.4954(3) 0.3361(2) 0.0702(9) Uani 1 1 d . . .
O2 O 0.9238(5) 0.2392(2) 0.51412(16) 0.0528(7) Uani 1 1 d . . .
C1 C 0.9137(6) 0.4037(3) 0.3141(2) 0.0486(9) Uani 1 1 d . . .
C2 C 0.9594(5) 0.3087(3) 0.3774(2) 0.0463(9) Uani 1 1 d . . .
H2A H 0.8965 0.2349 0.3635 0.056 Uiso 1 1 calc R . .
H2B H 1.0901 0.2929 0.3762 0.056 Uiso 1 1 calc R . .
C3 C 0.9063(5) 0.3450(3) 0.4603(2) 0.0472(8) Uani 1 1 d . . .
H3 H 0.7777 0.3702 0.4596 0.057 Uiso 1 1 calc R . .
C4 C 1.0193(6) 0.4422(4) 0.5014(3) 0.0535(10) Uani 1 1 d U . .
H4A H 1.1397 0.4491 0.4769 0.064 Uiso 1 1 calc R . .
H4B H 0.9580 0.5192 0.4987 0.064 Uiso 1 1 calc R . .
C5 C 1.0321(5) 0.3987(3) 0.5869(2) 0.0438(9) Uani 1 1 d U . .
C6 C 0.9769(5) 0.2808(3) 0.5876(2) 0.0422(9) Uani 1 1 d . . .
C7 C 0.9768(6) 0.2122(4) 0.6573(3) 0.0557(10) Uani 1 1 d . . .
H7 H 0.9388 0.1327 0.6565 0.067 Uiso 1 1 calc R . .
C8 C 1.0358(7) 0.2666(4) 0.7289(2) 0.0623(13) Uani 1 1 d . . .
H8 H 1.0368 0.2230 0.7770 0.075 Uiso 1 1 calc R . .
C9 C 1.0931(7) 0.3853(4) 0.7290(2) 0.0639(12) Uani 1 1 d . . .
H9 H 1.1314 0.4209 0.7771 0.077 Uiso 1 1 calc R . .
C10 C 1.0931(6) 0.4506(4) 0.6577(3) 0.0557(10) Uani 1 1 d . . .
H10 H 1.1342 0.5294 0.6575 0.067 Uiso 1 1 calc R . .
C11 C 0.9585(5) 0.3833(3) 0.2285(2) 0.0426(9) Uani 1 1 d . . .
C12 C 1.0519(6) 0.2820(3) 0.2010(2) 0.0498(10) Uani 1 1 d . . .
H12 H 1.0894 0.2240 0.2380 0.060 Uiso 1 1 calc R . .
C13 C 1.0894(7) 0.2668(4) 0.1191(2) 0.0559(10) Uani 1 1 d . . .
H13 H 1.1500 0.1985 0.1011 0.067 Uiso 1 1 calc R . .
C14 C 1.0369(6) 0.3524(4) 0.0654(2) 0.0516(10) Uani 1 1 d . . .
C15 C 0.9457(7) 0.4541(4) 0.0901(3) 0.0610(12) Uani 1 1 d . . .
H15 H 0.9124 0.5125 0.0526 0.073 Uiso 1 1 calc R . .
C16 C 0.9049(7) 0.4680(3) 0.1707(3) 0.0584(11) Uani 1 1 d . . .
H16 H 0.8400 0.5353 0.1874 0.070 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 0.1019(4) 0.0997(4) 0.0416(2) -0.0002(3) -0.0006(3) -0.0151(4)
O1 0.095(2) 0.0467(17) 0.068(2) -0.0058(15) 0.0036(18) 0.0188(17)
O2 0.0640(18) 0.0468(14) 0.0478(14) 0.0007(12) 0.0032(14) -0.0113(14)
C1 0.053(2) 0.040(2) 0.053(2) 0.0006(17) -0.008(2) -0.002(2)
C2 0.048(2) 0.045(2) 0.046(2) 0.0010(17) -0.0016(16) 0.0038(19)
C3 0.0487(19) 0.047(2) 0.046(2) 0.0016(18) 0.002(2) 0.003(2)
C4 0.062(3) 0.043(2) 0.0552(19) 0.0014(18) -0.007(2) -0.0048(19)
C5 0.042(2) 0.044(2) 0.0459(17) -0.0089(16) 0.0022(17) -0.0025(18)
C6 0.036(2) 0.053(2) 0.037(2) -0.0022(17) 0.0017(15) 0.0000(17)
C7 0.051(2) 0.057(2) 0.059(3) 0.008(2) 0.007(2) -0.003(2)
C8 0.067(3) 0.084(3) 0.036(2) 0.009(2) 0.005(2) 0.010(3)
C9 0.073(3) 0.079(3) 0.039(2) -0.010(2) 0.006(2) -0.002(3)
C10 0.058(3) 0.051(2) 0.058(2) -0.0149(19) 0.000(2) -0.002(2)
C11 0.045(2) 0.0395(19) 0.043(2) -0.0001(17) -0.0016(16) -0.0033(17)
C12 0.062(3) 0.0397(19) 0.048(2) 0.0060(17) -0.0058(19) 0.003(2)
C13 0.066(3) 0.052(2) 0.049(2) -0.0006(18) -0.001(2) 0.002(2)
C14 0.060(2) 0.062(3) 0.0331(19) 0.0014(17) -0.0053(16) -0.011(2)
C15 0.075(3) 0.061(3) 0.047(2) 0.013(2) -0.014(2) 0.004(2)
C16 0.065(3) 0.043(2) 0.067(3) 0.0038(19) -0.007(2) 0.007(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
Br1 C14 1.900(4) . ?
O1 C1 1.218(5) . ?
O2 C6 1.354(4) . ?
O2 C3 1.482(4) . ?
C1 C11 1.466(5) . ?
C1 C2 1.525(5) . ?
C2 C3 1.478(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.493(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.377(5) . ?
C5 C6 1.377(5) . ?
C6 C7 1.380(6) . ?
C7 C8 1.395(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.397(5) . ?
C11 C16 1.398(5) . ?
C12 C13 1.389(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(6) . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 H16 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
C6 O2 C3 106.7(3) . . ?
O1 C1 C11 121.2(4) . . ?
O1 C1 C2 118.7(4) . . ?
C11 C1 C2 120.1(3) . . ?
C3 C2 C1 112.6(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 O2 108.2(3) . . ?
C2 C3 C4 117.8(3) . . ?
O2 C3 C4 104.8(3) . . ?
C2 C3 H3 108.6 . . ?
O2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C5 C4 C3 102.8(3) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C10 C5 C6 119.3(4) . . ?
C10 C5 C4 133.0(4) . . ?
C6 C5 C4 107.6(3) . . ?
O2 C6 C7 123.7(3) . . ?
O2 C6 C5 113.8(3) . . ?
C7 C6 C5 122.6(4) . . ?
C6 C7 C8 117.5(4) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 119.9(4) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C16 117.6(4) . . ?
C12 C11 C1 123.1(3) . . ?
C16 C11 C1 119.2(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.6(4) . . ?
C13 C14 Br1 118.7(3) . . ?
C15 C14 Br1 119.7(3) . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?

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
O1 C1 C2 C3 -1.3(5) . . . . ?
C11 C1 C2 C3 179.4(4) . . . . ?
C1 C2 C3 O2 169.5(3) . . . . ?
C1 C2 C3 C4 -72.0(4) . . . . ?
C6 O2 C3 C2 146.3(3) . . . . ?
C6 O2 C3 C4 19.9(4) . . . . ?
C2 C3 C4 C5 -140.3(3) . . . . ?
O2 C3 C4 C5 -20.0(4) . . . . ?
C3 C4 C5 C10 -169.8(4) . . . . ?
C3 C4 C5 C6 13.7(4) . . . . ?
C3 O2 C6 C7 168.2(4) . . . . ?
C3 O2 C6 C5 -11.9(4) . . . . ?
C10 C5 C6 O2 -178.6(4) . . . . ?
C4 C5 C6 O2 -1.6(4) . . . . ?
C10 C5 C6 C7 1.3(6) . . . . ?
C4 C5 C6 C7 178.3(4) . . . . ?
O2 C6 C7 C8 179.8(4) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 C7 C8 C9 -0.3(7) . . . . ?
C7 C8 C9 C10 -0.4(8) . . . . ?
C6 C5 C10 C9 -2.0(6) . . . . ?
C4 C5 C10 C9 -178.1(5) . . . . ?
C8 C9 C10 C5 1.6(7) . . . . ?
O1 C1 C11 C12 177.1(4) . . . . ?
C2 C1 C11 C12 -3.6(6) . . . . ?
O1 C1 C11 C16 -3.4(6) . . . . ?
C2 C1 C11 C16 175.9(4) . . . . ?
C16 C11 C12 C13 0.0(6) . . . . ?
C1 C11 C12 C13 179.5(4) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C12 C13 C14 Br1 -179.6(3) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
Br1 C14 C15 C16 178.1(4) . . . . ?
C14 C15 C16 C11 2.0(7) . . . . ?
C12 C11 C16 C15 -1.5(6) . . . . ?
C1 C11 C16 C15 179.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O1 0.93 2.49 3.164(5) 129.0 3_745

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 937446'
#######################################################################
#
#                 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
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd212491

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Br N2 O2'
_chemical_formula_weight         437.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.1604(7)
_cell_length_b                   13.8657(19)
_cell_length_c                   14.351(2)
_cell_angle_alpha                104.433(3)
_cell_angle_beta                 90.414(3)
_cell_angle_gamma                95.735(3)
_cell_volume                     988.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1812
_cell_measurement_theta_min      4.733
_cell_measurement_theta_max      46.445

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.078
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    2.100
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.55005
_exptl_absorpt_correction_T_max  1.00000
_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            5735
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3686
_reflns_number_gt                2688
_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^)+(0.0000P)^2^+8.2221P] 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_number_reflns         3686
_refine_ls_number_parameters     338
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.2364
_refine_ls_wR_factor_gt          0.2263
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.129
_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
Br1 Br 0.5294(2) 0.87302(8) 0.44594(9) 0.0812(5) Uani 1 1 d . . .
N1 N 1.3544(13) 0.5148(5) 0.4144(5) 0.0510(17) Uani 1 1 d . . .
O1 O 1.5081(13) 0.4360(4) 0.3896(4) 0.0592(16) Uani 1 1 d . . .
H1 H 1.5940 0.4335 0.4371 0.089 Uiso 1 1 calc R . .
O2 O 0.949(2) 0.4639(9) 0.1373(8) 0.038(2) Uani 0.50 1 d P A 1
N2 N 0.837(3) 0.2640(12) 0.1583(13) 0.055(3) Uani 0.50 1 d PU A 1
C3 C 1.114(4) 0.4098(10) 0.1781(12) 0.068(5) Uani 0.60 1 d PDU A 1
H3 H 1.2165 0.3745 0.1255 0.082 Uiso 0.60 1 calc PR A 1
C5 C 0.715(4) 0.2965(17) 0.0852(17) 0.053(3) Uani 0.50 1 d PU A 1
C6 C 0.776(3) 0.3937(15) 0.0739(12) 0.045(3) Uani 0.50 1 d PU A 1
C7 C 0.661(3) 0.4254(14) 0.0010(12) 0.053(3) Uani 0.50 1 d PU A 1
H7 H 0.7079 0.4889 -0.0081 0.064 Uiso 0.50 1 calc PR A 1
C8 C 0.473(4) 0.3593(16) -0.0582(13) 0.063(3) Uani 0.50 1 d PU A 1
H8 H 0.3827 0.3820 -0.1035 0.076 Uiso 0.50 1 calc PR A 1
C9 C 0.416(4) 0.2650(19) -0.0533(15) 0.066(4) Uani 0.50 1 d PU A 1
H9 H 0.2916 0.2226 -0.0956 0.079 Uiso 0.50 1 calc PR A 1
C10 C 0.542(3) 0.2311(12) 0.0152(11) 0.063(4) Uani 0.50 1 d PU A 1
H10 H 0.5122 0.1639 0.0155 0.076 Uiso 0.50 1 calc PR A 1
C17 C 0.692(3) 0.1915(12) 0.2024(11) 0.061(4) Uani 0.50 1 d PRU A 1
H17A H 0.5443 0.1589 0.1600 0.074 Uiso 0.50 1 calc PR A 1
H17B H 0.6231 0.2278 0.2623 0.074 Uiso 0.50 1 calc PR A 1
O2' O 1.009(2) 0.3999(10) 0.1060(8) 0.050(3) Uani 0.50 1 d P A 2
N2' N 0.739(3) 0.2647(13) 0.1958(11) 0.048(3) Uani 0.50 1 d PU A 2
C3' C 1.015(3) 0.4297(11) 0.2088(15) 0.041(6) Uani 0.40 1 d PDU A 2
H3' H 0.8721 0.4689 0.2351 0.050 Uiso 0.40 1 calc PR A 2
C5' C 0.674(4) 0.2642(15) 0.1017(14) 0.045(3) Uani 0.50 1 d PU A 2
C6' C 0.796(4) 0.3330(17) 0.0587(13) 0.048(3) Uani 0.50 1 d PU A 2
C7' C 0.734(4) 0.3404(14) -0.0314(12) 0.057(3) Uani 0.50 1 d PU A 2
H7' H 0.8271 0.3887 -0.0562 0.068 Uiso 0.50 1 calc PR A 2
C8' C 0.536(4) 0.2780(16) -0.0866(15) 0.061(3) Uani 0.50 1 d PU A 2
H8' H 0.4900 0.2817 -0.1483 0.074 Uiso 0.50 1 calc PR A 2
C9' C 0.409(4) 0.2091(16) -0.0422(14) 0.056(3) Uani 0.50 1 d PU A 2
H9' H 0.2739 0.1651 -0.0769 0.067 Uiso 0.50 1 calc PR A 2
C10' C 0.467(3) 0.2006(10) 0.0471(9) 0.050(3) Uani 0.50 1 d PU A 2
H10' H 0.3709 0.1533 0.0725 0.060 Uiso 0.50 1 calc PR A 2
C17' C 0.649(3) 0.1855(10) 0.2418(9) 0.054(4) Uani 0.50 1 d PRU A 2
H17C H 0.4800 0.1537 0.2147 0.065 Uiso 0.50 1 calc PR A 2
H17D H 0.6326 0.2132 0.3103 0.065 Uiso 0.50 1 calc PR A 2
C1 C 1.2528(14) 0.5375(5) 0.3424(5) 0.0378(16) Uani 1 1 d . A .
C2 C 1.2981(16) 0.4872(6) 0.2419(6) 0.053(2) Uani 1 1 d D . .
H2A H 1.4598 0.4573 0.2430 0.064 Uiso 0.50 1 calc PR A 1
H2B H 1.3329 0.5400 0.2089 0.064 Uiso 0.50 1 calc PR A 1
H2C H 1.3482 0.5343 0.2060 0.064 Uiso 0.50 1 d PR A 2
H2D H 1.4289 0.4419 0.2390 0.064 Uiso 0.50 1 d PR A 2
C4 C 0.9971(17) 0.3302(7) 0.2298(7) 0.062(2) Uani 1 1 d D . .
H4A H 1.1327 0.2965 0.2517 0.074 Uiso 0.50 1 calc PR A 1
H4B H 0.8972 0.3604 0.2844 0.074 Uiso 0.50 1 calc PR A 1
H4C H 1.1371 0.2948 0.1975 0.074 Uiso 0.50 1 d PR A 2
H4D H 1.0183 0.3414 0.2965 0.074 Uiso 0.50 1 d PR A 2
C11 C 1.0755(15) 0.6180(6) 0.3677(6) 0.0422(18) Uani 1 1 d . . .
C12 C 0.9754(17) 0.6454(7) 0.4575(6) 0.055(2) Uani 1 1 d . A .
H12 H 1.0171 0.6120 0.5034 0.066 Uiso 1 1 calc R . .
C13 C 0.8134(19) 0.7215(7) 0.4820(7) 0.064(3) Uani 1 1 d . . .
H13 H 0.7493 0.7394 0.5436 0.077 Uiso 1 1 calc R A .
C14 C 0.7500(16) 0.7694(6) 0.4143(7) 0.052(2) Uani 1 1 d . A .
C15 C 0.8443(19) 0.7444(7) 0.3246(7) 0.062(2) Uani 1 1 d . . .
H15 H 0.8012 0.7786 0.2795 0.074 Uiso 1 1 calc R A .
C16 C 1.0054(18) 0.6678(6) 0.2996(6) 0.055(2) Uani 1 1 d . A .
H16 H 1.0664 0.6499 0.2375 0.066 Uiso 1 1 calc R . .
C18 C 0.851(2) 0.1080(7) 0.2245(8) 0.071(3) Uani 1 1 d . . .
C19 C 0.963(3) 0.0597(10) 0.1439(9) 0.119(6) Uani 1 1 d . A .
H19 H 0.9385 0.0780 0.0866 0.143 Uiso 1 1 calc R . .
C20 C 1.113(3) -0.0168(10) 0.1459(12) 0.124(6) Uani 1 1 d . . .
H20 H 1.1794 -0.0525 0.0890 0.149 Uiso 1 1 calc R A .
C21 C 1.162(3) -0.0398(9) 0.2264(11) 0.092(4) Uani 1 1 d . A .
H21 H 1.2706 -0.0892 0.2275 0.111 Uiso 1 1 calc R . .
C22 C 1.057(3) 0.0078(10) 0.3070(10) 0.096(4) Uani 1 1 d . . .
H22 H 1.0934 -0.0091 0.3641 0.116 Uiso 1 1 calc R A .
C23 C 0.897(2) 0.0807(8) 0.3082(8) 0.083(3) Uani 1 1 d . A .
H23 H 0.8211 0.1115 0.3650 0.100 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 0.0752(7) 0.0585(6) 0.1092(10) 0.0115(5) -0.0056(6) 0.0291(5)
N1 0.054(4) 0.057(4) 0.045(4) 0.012(3) -0.002(3) 0.024(3)
O1 0.075(4) 0.064(4) 0.047(3) 0.017(3) 0.002(3) 0.036(3)
O2 0.035(6) 0.043(6) 0.042(7) 0.019(5) -0.004(5) 0.008(5)
N2 0.048(6) 0.050(6) 0.066(8) 0.016(6) -0.001(6) 0.003(5)
C3 0.110(13) 0.034(7) 0.060(11) -0.004(7) -0.036(10) 0.041(9)
C5 0.043(6) 0.059(6) 0.055(6) 0.011(6) -0.003(5) 0.001(5)
C6 0.037(6) 0.057(6) 0.044(6) 0.020(6) 0.002(5) -0.006(6)
C7 0.043(6) 0.071(7) 0.043(6) 0.020(6) -0.004(5) -0.016(6)
C8 0.053(7) 0.085(7) 0.045(6) 0.015(6) -0.008(6) -0.018(6)
C9 0.055(7) 0.082(8) 0.047(7) 0.003(7) -0.004(6) -0.016(7)
C10 0.055(7) 0.072(7) 0.052(7) 0.001(6) -0.003(6) -0.005(6)
C17 0.052(8) 0.058(8) 0.073(10) 0.017(8) 0.002(8) 0.004(7)
O2' 0.049(7) 0.070(9) 0.035(7) 0.025(6) -0.012(5) -0.010(7)
N2' 0.054(7) 0.055(6) 0.038(6) 0.016(5) 0.012(5) 0.006(6)
C3' 0.051(11) 0.035(10) 0.033(10) -0.011(8) 0.001(8) 0.031(9)
C5' 0.049(6) 0.053(6) 0.038(5) 0.018(5) 0.007(5) 0.006(5)
C6' 0.050(6) 0.060(7) 0.037(6) 0.019(6) -0.001(5) 0.003(6)
C7' 0.058(7) 0.069(7) 0.046(6) 0.023(6) -0.007(5) -0.007(6)
C8' 0.062(7) 0.070(7) 0.050(6) 0.018(6) -0.011(6) -0.008(6)
C9' 0.057(7) 0.062(7) 0.047(6) 0.013(6) -0.009(6) -0.003(6)
C10' 0.051(6) 0.054(6) 0.045(6) 0.015(5) 0.004(5) 0.002(6)
C17' 0.063(8) 0.063(8) 0.040(7) 0.017(7) 0.020(7) 0.009(7)
C1 0.033(4) 0.042(4) 0.038(4) 0.011(3) -0.001(3) -0.002(3)
C2 0.062(5) 0.060(5) 0.044(5) 0.019(4) -0.003(4) 0.023(4)
C4 0.047(5) 0.076(6) 0.061(6) 0.014(5) -0.012(4) 0.015(5)
C11 0.038(4) 0.044(4) 0.045(5) 0.014(3) -0.009(3) 0.001(3)
C12 0.059(5) 0.062(5) 0.055(5) 0.028(4) 0.009(4) 0.021(4)
C13 0.077(7) 0.065(6) 0.057(6) 0.022(5) 0.017(5) 0.027(5)
C14 0.047(5) 0.039(4) 0.068(6) 0.011(4) -0.012(4) 0.005(4)
C15 0.082(7) 0.059(5) 0.049(5) 0.017(4) -0.017(5) 0.021(5)
C16 0.072(6) 0.053(5) 0.038(5) 0.007(4) -0.012(4) 0.016(4)
C18 0.078(7) 0.053(5) 0.074(7) 0.001(5) -0.023(6) 0.011(5)
C19 0.214(17) 0.095(9) 0.058(7) 0.015(7) -0.012(9) 0.073(11)
C20 0.185(17) 0.085(9) 0.112(12) 0.021(8) 0.040(11) 0.065(10)
C21 0.110(10) 0.079(8) 0.103(10) 0.044(8) 0.007(8) 0.025(7)
C22 0.113(10) 0.088(9) 0.098(10) 0.051(8) -0.044(8) -0.006(8)
C23 0.101(9) 0.071(7) 0.072(7) 0.009(6) 0.010(6) 0.006(6)

_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 C14 1.891(8) . ?
N1 C1 1.276(9) . ?
N1 O1 1.390(8) . ?
O1 H1 0.8200 . ?
O2 C6 1.39(2) . ?
O2 C3 1.405(18) . ?
N2 C4 1.394(18) . ?
N2 C5 1.41(3) . ?
N2 C17 1.47(2) . ?
C3 C2 1.478(14) . ?
C3 C4 1.555(15) . ?
C3 H3 0.9800 . ?
C5 C6 1.40(3) . ?
C5 C10 1.42(2) . ?
C6 C7 1.38(2) . ?
C7 C8 1.39(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.33(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.38(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C17 C18 1.577(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O2' C6' 1.41(2) . ?
O2' C3' 1.43(2) . ?
N2' C5' 1.39(2) . ?
N2' C17' 1.456(19) . ?
N2' C4 1.537(19) . ?
C3' C4 1.478(16) . ?
C3' C2 1.603(16) . ?
C3' H3' 0.9800 . ?
C5' C6' 1.37(2) . ?
C5' C10' 1.41(2) . ?
C6' C7' 1.36(2) . ?
C7' C8' 1.37(2) . ?
C7' H7' 0.9300 . ?
C8' C9' 1.39(3) . ?
C8' H8' 0.9300 . ?
C9' C10' 1.35(2) . ?
C9' H9' 0.9300 . ?
C10' H10' 0.9300 . ?
C17' C18 1.549(17) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C1 C2 1.469(11) . ?
C1 C11 1.490(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9470 . ?
C2 H2D 0.9607 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9689 . ?
C4 H4D 0.9347 . ?
C11 C12 1.369(11) . ?
C11 C16 1.394(11) . ?
C12 C13 1.390(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.353(13) . ?
C15 C16 1.393(12) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C19 1.349(16) . ?
C18 C23 1.373(15) . ?
C19 C20 1.380(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.303(18) . ?
C20 H20 0.9300 . ?
C21 C22 1.329(17) . ?
C21 H21 0.9300 . ?
C22 C23 1.362(17) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 O1 114.1(6) . . ?
N1 O1 H1 109.5 . . ?
C6 O2 C3 106.8(12) . . ?
C4 N2 C5 121.6(15) . . ?
C4 N2 C17 107.8(14) . . ?
C5 N2 C17 119.4(16) . . ?
O2 C3 C2 104.7(10) . . ?
O2 C3 C4 120.0(14) . . ?
C2 C3 C4 111.9(10) . . ?
O2 C3 H3 106.5 . . ?
C2 C3 H3 106.5 . . ?
C4 C3 H3 106.5 . . ?
C6 C5 N2 121.1(17) . . ?
C6 C5 C10 116.7(19) . . ?
N2 C5 C10 122.0(19) . . ?
C7 C6 O2 116.9(15) . . ?
C7 C6 C5 121.3(17) . . ?
O2 C6 C5 121.8(15) . . ?
C6 C7 C8 117.8(17) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C9 C8 C7 123.2(19) . . ?
C9 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C8 C9 C10 119.2(18) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 121.2(18) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
N2 C17 C18 115.8(12) . . ?
N2 C17 H17A 108.3 . . ?
C18 C17 H17A 108.3 . . ?
N2 C17 H17B 108.3 . . ?
C18 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C6' O2' C3' 117.8(13) . . ?
C5' N2' C17' 124.3(15) . . ?
C5' N2' C4 110.8(14) . . ?
C17' N2' C4 120.2(12) . . ?
O2' C3' C4 99.7(12) . . ?
O2' C3' C2 106.5(13) . . ?
C4 C3' C2 109.2(11) . . ?
O2' C3' H3' 113.4 . . ?
C4 C3' H3' 113.4 . . ?
C2 C3' H3' 113.4 . . ?
C6' C5' N2' 121.0(18) . . ?
C6' C5' C10' 115.3(16) . . ?
N2' C5' C10' 123.5(16) . . ?
C7' C6' C5' 124.3(19) . . ?
C7' C6' O2' 115.3(18) . . ?
C5' C6' O2' 120.4(16) . . ?
C6' C7' C8' 121.5(19) . . ?
C6' C7' H7' 119.3 . . ?
C8' C7' H7' 119.3 . . ?
C7' C8' C9' 114.3(17) . . ?
C7' C8' H8' 122.9 . . ?
C9' C8' H8' 122.9 . . ?
C10' C9' C8' 125.3(18) . . ?
C10' C9' H9' 117.3 . . ?
C8' C9' H9' 117.3 . . ?
C9' C10' C5' 119.4(15) . . ?
C9' C10' H10' 120.3 . . ?
C5' C10' H10' 120.3 . . ?
N2' C17' C18 108.1(11) . . ?
N2' C17' H17C 110.1 . . ?
C18 C17' H17C 110.1 . . ?
N2' C17' H17D 110.1 . . ?
C18 C17' H17D 110.1 . . ?
H17C C17' H17D 108.4 . . ?
N1 C1 C2 123.4(7) . . ?
N1 C1 C11 114.8(7) . . ?
C2 C1 C11 121.8(7) . . ?
C1 C2 C3 125.3(10) . . ?
C1 C2 C3' 100.6(9) . . ?
C3 C2 C3' 26.3(8) . . ?
C1 C2 H2A 106.0 . . ?
C3 C2 H2A 106.0 . . ?
C3' C2 H2A 126.9 . . ?
C1 C2 H2B 106.0 . . ?
C3 C2 H2B 106.0 . . ?
C3' C2 H2B 109.2 . . ?
H2A C2 H2B 106.3 . . ?
C1 C2 H2C 111.1 . . ?
C3 C2 H2C 105.5 . . ?
C3' C2 H2C 112.0 . . ?
H2A C2 H2C 100.0 . . ?
H2B C2 H2C 6.9 . . ?
C1 C2 H2D 110.4 . . ?
C3 C2 H2D 92.7 . . ?
C3' C2 H2D 112.4 . . ?
H2A C2 H2D 14.7 . . ?
H2B C2 H2D 116.8 . . ?
H2C C2 H2D 110.1 . . ?
N2 C4 C3' 107.7(11) . . ?
N2 C4 N2' 28.7(7) . . ?
C3' C4 N2' 114.4(10) . . ?
N2 C4 C3 103.1(11) . . ?
C3' C4 C3 27.0(7) . . ?
N2' C4 C3 122.5(10) . . ?
N2 C4 H4A 111.1 . . ?
C3' C4 H4A 129.3 . . ?
N2' C4 H4A 115.4 . . ?
C3 C4 H4A 111.1 . . ?
N2 C4 H4B 111.1 . . ?
C3' C4 H4B 85.1 . . ?
N2' C4 H4B 83.6 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
N2 C4 H4C 84.7 . . ?
C3' C4 H4C 108.0 . . ?
N2' C4 H4C 107.9 . . ?
C3 C4 H4C 81.1 . . ?
H4A C4 H4C 46.9 . . ?
H4B C4 H4C 155.9 . . ?
N2 C4 H4D 135.4 . . ?
C3' C4 H4D 106.7 . . ?
N2' C4 H4D 109.5 . . ?
C3 C4 H4D 120.2 . . ?
H4A C4 H4D 64.4 . . ?
H4B C4 H4D 45.5 . . ?
H4C C4 H4D 110.5 . . ?
C12 C11 C16 117.8(8) . . ?
C12 C11 C1 121.7(7) . . ?
C16 C11 C1 120.5(7) . . ?
C11 C12 C13 122.0(8) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 118.9(9) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 120.9(8) . . ?
C15 C14 Br1 119.4(7) . . ?
C13 C14 Br1 119.6(7) . . ?
C14 C15 C16 120.3(8) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.0(8) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C19 C18 C23 118.1(10) . . ?
C19 C18 C17' 132.0(11) . . ?
C23 C18 C17' 109.6(10) . . ?
C19 C18 C17 110.1(11) . . ?
C23 C18 C17 131.8(11) . . ?
C17' C18 C17 23.2(6) . . ?
C18 C19 C20 120.4(12) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.8(13) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.7(13) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 121.9(12) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C18 119.0(11) . . ?
C22 C23 H23 120.5 . . ?
C18 C23 H23 120.5 . . ?

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
C6 O2 C3 C2 178.2(12) . . . . ?
C6 O2 C3 C4 -55.3(18) . . . . ?
C4 N2 C5 C6 8(3) . . . . ?
C17 N2 C5 C6 147.8(19) . . . . ?
C4 N2 C5 C10 -176.7(16) . . . . ?
C17 N2 C5 C10 -37(3) . . . . ?
C3 O2 C6 C7 -157.1(16) . . . . ?
C3 O2 C6 C5 25(2) . . . . ?
N2 C5 C6 C7 178.7(18) . . . . ?
C10 C5 C6 C7 4(3) . . . . ?
N2 C5 C6 O2 -4(3) . . . . ?
C10 C5 C6 O2 -178.7(15) . . . . ?
O2 C6 C7 C8 -174.9(16) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C6 C7 C8 C9 -6(3) . . . . ?
C7 C8 C9 C10 2(3) . . . . ?
C8 C9 C10 C5 5(3) . . . . ?
C6 C5 C10 C9 -8(3) . . . . ?
N2 C5 C10 C9 177.2(19) . . . . ?
C4 N2 C17 C18 -75.5(15) . . . . ?
C5 N2 C17 C18 140.2(16) . . . . ?
C6' O2' C3' C4 56.0(18) . . . . ?
C6' O2' C3' C2 169.5(14) . . . . ?
C17' N2' C5' C6' -170.1(17) . . . . ?
C4 N2' C5' C6' -15(3) . . . . ?
C17' N2' C5' C10' 16(3) . . . . ?
C4 N2' C5' C10' 171.4(15) . . . . ?
N2' C5' C6' C7' -176(2) . . . . ?
C10' C5' C6' C7' -2(3) . . . . ?
N2' C5' C6' O2' 6(3) . . . . ?
C10' C5' C6' O2' -179.1(16) . . . . ?
C3' O2' C6' C7' 152.2(17) . . . . ?
C3' O2' C6' C5' -31(3) . . . . ?
C5' C6' C7' C8' 1(3) . . . . ?
O2' C6' C7' C8' 178.1(19) . . . . ?
C6' C7' C8' C9' 0(3) . . . . ?
C7' C8' C9' C10' 0(3) . . . . ?
C8' C9' C10' C5' -1(3) . . . . ?
C6' C5' C10' C9' 2(3) . . . . ?
N2' C5' C10' C9' 176.4(18) . . . . ?
C5' N2' C17' C18 90.6(19) . . . . ?
C4 N2' C17' C18 -62.8(15) . . . . ?
O1 N1 C1 C2 -1.5(11) . . . . ?
O1 N1 C1 C11 176.7(6) . . . . ?
N1 C1 C2 C3 101.9(11) . . . . ?
C11 C1 C2 C3 -76.2(12) . . . . ?
N1 C1 C2 C3' 111.8(10) . . . . ?
C11 C1 C2 C3' -66.3(10) . . . . ?
O2 C3 C2 C1 86.5(14) . . . . ?
C4 C3 C2 C1 -44.9(16) . . . . ?
O2 C3 C2 C3' 64(2) . . . . ?
C4 C3 C2 C3' -67(2) . . . . ?
O2' C3' C2 C1 164.3(11) . . . . ?
C4 C3' C2 C1 -88.8(13) . . . . ?
O2' C3' C2 C3 -34.2(18) . . . . ?
C4 C3' C2 C3 72.7(18) . . . . ?
C5 N2 C4 C3' -3(2) . . . . ?
C17 N2 C4 C3' -146.0(13) . . . . ?
C5 N2 C4 N2' 106(3) . . . . ?
C17 N2 C4 N2' -37.3(19) . . . . ?
C5 N2 C4 C3 -30(2) . . . . ?
C17 N2 C4 C3 -173.6(12) . . . . ?
O2' C3' C4 N2 -35.2(15) . . . . ?
C2 C3' C4 N2 -146.6(13) . . . . ?
O2' C3' C4 N2' -65.1(15) . . . . ?
C2 C3' C4 N2' -176.5(11) . . . . ?
O2' C3' C4 C3 49.0(18) . . . . ?
C2 C3' C4 C3 -62.4(17) . . . . ?
C5' N2' C4 N2 -34.7(19) . . . . ?
C17' N2' C4 N2 122(3) . . . . ?
C5' N2' C4 C3' 47.6(19) . . . . ?
C17' N2' C4 C3' -155.8(14) . . . . ?
C5' N2' C4 C3 18(2) . . . . ?
C17' N2' C4 C3 174.8(13) . . . . ?
O2 C3 C4 N2 58.1(17) . . . . ?
C2 C3 C4 N2 -178.7(12) . . . . ?
O2 C3 C4 C3' -45(2) . . . . ?
C2 C3 C4 C3' 78(2) . . . . ?
O2 C3 C4 N2' 35(2) . . . . ?
C2 C3 C4 N2' 158.1(12) . . . . ?
N1 C1 C11 C12 -16.9(11) . . . . ?
C2 C1 C11 C12 161.4(8) . . . . ?
N1 C1 C11 C16 163.4(8) . . . . ?
C2 C1 C11 C16 -18.4(11) . . . . ?
C16 C11 C12 C13 -1.3(13) . . . . ?
C1 C11 C12 C13 178.9(8) . . . . ?
C11 C12 C13 C14 0.8(15) . . . . ?
C12 C13 C14 C15 -0.6(14) . . . . ?
C12 C13 C14 Br1 179.9(7) . . . . ?
C13 C14 C15 C16 1.0(14) . . . . ?
Br1 C14 C15 C16 -179.5(7) . . . . ?
C14 C15 C16 C11 -1.5(14) . . . . ?
C12 C11 C16 C15 1.6(13) . . . . ?
C1 C11 C16 C15 -178.6(8) . . . . ?
N2' C17' C18 C19 -50.4(19) . . . . ?
N2' C17' C18 C23 136.2(11) . . . . ?
N2' C17' C18 C17 -28.8(19) . . . . ?
N2 C17 C18 C19 -54.5(16) . . . . ?
N2 C17 C18 C23 123.3(15) . . . . ?
N2 C17 C18 C17' 142(3) . . . . ?
C23 C18 C19 C20 2(2) . . . . ?
C17' C18 C19 C20 -171.2(14) . . . . ?
C17 C18 C19 C20 179.9(15) . . . . ?
C18 C19 C20 C21 -4(3) . . . . ?
C19 C20 C21 C22 3(3) . . . . ?
C20 C21 C22 C23 0(2) . . . . ?
C21 C22 C23 C18 -2.2(19) . . . . ?
C19 C18 C23 C22 1.2(18) . . . . ?
C17' C18 C23 C22 175.7(11) . . . . ?
C17 C18 C23 C22 -176.4(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 2.08 2.793(9) 145.4 2_866

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.095
_database_code_depnum_ccdc_archive 'CCDC 937447'