# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_mo_molan114_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.32
_chemical_absolute_configuration sys

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   8.2349(3)
_cell_length_b                   12.5658(4)
_cell_length_c                   12.9900(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1344.18(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55490
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.19
_reflns_number_total             2992
_reflns_number_gt                2861
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0414P)²+0.3646P] where P=(Fo²+2Fc²)/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_number_reflns         2992
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
C9 C 0.37360(14) 0.29246(10) 0.21376(9) 0.0161(2) Uani 1 1 d . . .
C1 C 0.11188(14) 0.31750(10) 0.40750(10) 0.0158(2) Uani 1 1 d . . .
C7 C 0.18916(15) 0.29845(10) 0.19977(9) 0.0157(2) Uani 1 1 d . . .
C11 C 0.62231(17) 0.19275(12) 0.19114(11) 0.0259(3) Uani 1 1 d . . .
H11 H 0.6761 0.1293 0.1708 0.031 Uiso 1 1 calc R . .
C8 C 0.14473(15) 0.20837(9) 0.36093(9) 0.0159(2) Uani 1 1 d . . .
H8 H 0.2599 0.1873 0.3743 0.019 Uiso 1 1 calc R . .
C2 C 0.09396(16) 0.32997(10) 0.51345(10) 0.0197(3) Uani 1 1 d . . .
H2 H 0.1087 0.2703 0.5574 0.024 Uiso 1 1 calc R . .
C16 C 0.03232(17) 0.12703(10) 0.40573(10) 0.0202(3) Uani 1 1 d . . .
H16 H -0.0800 0.1325 0.3900 0.024 Uiso 1 1 calc R . .
C3 C 0.05502(17) 0.42793(11) 0.55582(10) 0.0226(3) Uani 1 1 d . . .
H3 H 0.0459 0.4358 0.6283 0.027 Uiso 1 1 calc R . .
C15 C 0.14435(16) 0.28695(11) 0.08656(9) 0.0204(3) Uani 1 1 d . . .
H15A H 0.1887 0.2201 0.0598 0.031 Uiso 1 1 calc R . .
H15B H 0.1896 0.3468 0.0476 0.031 Uiso 1 1 calc R . .
H15C H 0.0259 0.2866 0.0794 0.031 Uiso 1 1 calc R . .
C5 C 0.04723(16) 0.50439(10) 0.38574(10) 0.0179(3) Uani 1 1 d . . .
H5 H 0.0283 0.5637 0.3420 0.021 Uiso 1 1 calc R . .
C14 C 0.46387(16) 0.37711(10) 0.25131(10) 0.0193(3) Uani 1 1 d . . .
H14 H 0.4104 0.4404 0.2727 0.023 Uiso 1 1 calc R . .
C4 C 0.02931(16) 0.51482(10) 0.49114(10) 0.0206(3) Uani 1 1 d . . .
H4 H -0.0007 0.5816 0.5196 0.025 Uiso 1 1 calc R . .
C6 C 0.09332(14) 0.40644(10) 0.34361(9) 0.0155(2) Uani 1 1 d . . .
C10 C 0.45401(16) 0.19951(10) 0.18445(10) 0.0211(3) Uani 1 1 d . . .
H10 H 0.3934 0.1405 0.1598 0.025 Uiso 1 1 calc R . .
C13 C 0.63269(16) 0.37007(12) 0.25786(11) 0.0250(3) Uani 1 1 d . . .
H13 H 0.6936 0.4286 0.2834 0.030 Uiso 1 1 calc R . .
C12 C 0.71167(16) 0.27827(13) 0.22733(11) 0.0267(3) Uani 1 1 d . . .
H12 H 0.8267 0.2739 0.2312 0.032 Uiso 1 1 calc R . .
C17 C 0.0799(2) 0.04818(11) 0.46577(11) 0.0288(3) Uani 1 1 d . . .
H17A H 0.1914 0.0406 0.4829 0.035 Uiso 1 1 calc R . .
H17B H 0.0025 -0.0010 0.4919 0.035 Uiso 1 1 calc R . .
O1 O 0.11433(10) 0.20958(7) 0.25161(6) 0.01666(19) Uani 1 1 d . . .
N1 N 0.12349(13) 0.39702(9) 0.23836(8) 0.0179(2) Uani 1 1 d . . .
H1 H 0.1028 0.4502 0.1963 0.022 Uiso 1 1 calc R . .


_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
C9 C14 1.3864(18) . ?
C9 C10 1.3955(18) . ?
C9 C7 1.5315(16) . ?
C1 C2 1.3929(18) . ?
C1 C6 1.4005(17) . ?
C1 C8 1.5230(17) . ?
C7 N1 1.4414(16) . ?
C7 O1 1.4423(14) . ?
C7 C15 1.5231(16) . ?
C11 C12 1.385(2) . ?
C11 C10 1.3913(18) . ?
C8 O1 1.4420(14) . ?
C8 C16 1.4967(17) . ?
C2 C3 1.3860(18) . ?
C16 C17 1.3204(19) . ?
C3 C4 1.3939(18) . ?
C5 C4 1.3833(18) . ?
C5 C6 1.3995(17) . ?
C14 C13 1.3957(18) . ?
C6 N1 1.3947(15) . ?
C13 C12 1.382(2) . ?

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
C14 C9 C10 118.93(11) . . ?
C14 C9 C7 122.39(12) . . ?
C10 C9 C7 118.64(11) . . ?
C2 C1 C6 118.95(11) . . ?
C2 C1 C8 120.84(11) . . ?
C6 C1 C8 120.16(11) . . ?
N1 C7 O1 110.04(9) . . ?
N1 C7 C15 109.04(10) . . ?
O1 C7 C15 105.89(10) . . ?
N1 C7 C9 111.91(10) . . ?
O1 C7 C9 109.29(10) . . ?
C15 C7 C9 110.50(10) . . ?
C12 C11 C10 120.21(13) . . ?
O1 C8 C16 106.43(10) . . ?
O1 C8 C1 110.54(9) . . ?
C16 C8 C1 110.52(10) . . ?
C3 C2 C1 121.12(12) . . ?
C17 C16 C8 123.97(13) . . ?
C2 C3 C4 119.43(12) . . ?
C4 C5 C6 119.95(11) . . ?
C9 C14 C13 120.45(13) . . ?
C5 C4 C3 120.41(12) . . ?
N1 C6 C5 120.42(11) . . ?
N1 C6 C1 119.59(11) . . ?
C5 C6 C1 119.98(11) . . ?
C11 C10 C9 120.45(13) . . ?
C12 C13 C14 120.27(13) . . ?
C13 C12 C11 119.67(12) . . ?
C8 O1 C7 113.19(9) . . ?
C6 N1 C7 118.73(10) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.19
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.041

_database_code_depnum_ccdc_archive 'CCDC 957090'
#######################################################################
#
#                 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_mo_molan093c_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Br N O'
_chemical_formula_weight         314.18

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   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   6.3154(5)
_cell_length_b                   8.1371(7)
_cell_length_c                   14.3362(12)
_cell_angle_alpha                85.222(3)
_cell_angle_beta                 78.520(3)
_cell_angle_gamma                70.043(3)
_cell_volume                     678.53(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      5.801
_cell_measurement_theta_max      53.933

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    3.019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_T_max  0.7728
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31603
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         27.13
_reflns_number_total             5756
_reflns_number_gt                4785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1061P)²+0.0000P] where P=(Fo²+2Fc²)/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   0.007(11)
_refine_ls_number_reflns         5756
_refine_ls_number_parameters     319
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.046
_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_1 Br -0.16293(7) 0.24554(6) 0.88805(4) 0.06805(19) Uani 1 1 d . . .
O1_1 O 0.3571(5) 0.5421(4) 0.4821(3) 0.0509(8) Uani 1 1 d . . .
N1_1 N 0.0014(6) 0.5137(5) 0.5490(3) 0.0456(8) Uani 1 1 d . . .
C1_1 C 0.0401(9) 0.2932(6) 0.7818(3) 0.0481(10) Uani 1 1 d . . .
C2_1 C 0.2734(10) 0.2332(7) 0.7806(4) 0.0564(12) Uani 1 1 d . . .
H2_1 H 0.3318 0.1703 0.8324 0.068 Uiso 1 1 calc R . .
C3_1 C 0.4175(9) 0.2671(7) 0.7026(4) 0.0538(12) Uani 1 1 d . . .
H3_1 H 0.5746 0.2271 0.7014 0.065 Uiso 1 1 calc R . .
C4_1 C 0.3306(8) 0.3617(6) 0.6244(3) 0.0444(9) Uani 1 1 d . . .
C5_1 C 0.0968(7) 0.4196(5) 0.6251(3) 0.0398(8) Uani 1 1 d . . .
C6_1 C -0.0500(8) 0.3851(6) 0.7052(3) 0.0448(9) Uani 1 1 d . . .
H6_1 H -0.2073 0.4237 0.7069 0.054 Uiso 1 1 calc R . .
C7_1 C 0.4851(8) 0.4002(6) 0.5369(4) 0.0468(10) Uani 1 1 d . . .
H7_1 H 0.6002 0.4369 0.5581 0.056 Uiso 1 1 calc R . .
C8_1 C 0.6084(9) 0.2468(6) 0.4742(4) 0.0497(10) Uani 1 1 d . . .
H8_1 H 0.5227 0.1865 0.4556 0.060 Uiso 1 1 calc R . .
C9_1 C 0.8254(9) 0.1928(8) 0.4445(4) 0.0574(13) Uani 1 1 d . . .
H9A_1 H 0.9155 0.2505 0.4620 0.069 Uiso 1 1 calc R . .
H9B_1 H 0.8929 0.0961 0.4055 0.069 Uiso 1 1 calc R . .
C10_1 C 0.1299(8) 0.5705(6) 0.4843(3) 0.0398(9) Uani 1 1 d . . .
C11_1 C 0.0478(5) 0.6757(4) 0.40363(19) 0.0430(9) Uani 1 1 d GU . .
C12_1 C 0.1977(4) 0.7214(4) 0.3297(2) 0.0558(11) Uani 1 1 d G . .
H12_1 H 0.3539 0.6821 0.3306 0.067 Uiso 1 1 calc R . .
C13_1 C 0.1141(6) 0.8258(5) 0.2545(2) 0.0680(17) Uani 1 1 d G . .
H13_1 H 0.2144 0.8564 0.2050 0.082 Uiso 1 1 calc R . .
C14_1 C -0.1194(6) 0.8845(5) 0.2531(2) 0.0663(14) Uani 1 1 d G . .
H14_1 H -0.1754 0.9544 0.2028 0.080 Uiso 1 1 calc R . .
C15_1 C -0.2693(4) 0.8389(5) 0.3270(3) 0.0618(13) Uani 1 1 d G . .
H15_1 H -0.4256 0.8782 0.3262 0.074 Uiso 1 1 calc R . .
C16_1 C -0.1857(4) 0.7345(4) 0.4023(2) 0.0554(12) Uani 1 1 d GU . .
H16_1 H -0.2860 0.7039 0.4517 0.066 Uiso 1 1 calc R . .
Br2_2 Br 1.32708(8) 0.25947(6) 1.24756(4) 0.0698(2) Uani 1 1 d . . .
O2_2 O 0.8144(5) 0.7059(5) 0.8894(2) 0.0543(8) Uani 1 1 d . . .
N2_2 N 1.1647(7) 0.6336(5) 0.9398(3) 0.0479(8) Uani 1 1 d . . .
C1_2 C 1.1232(9) 0.3967(6) 1.1684(3) 0.0488(10) Uani 1 1 d . . .
C2_2 C 0.8971(10) 0.4290(8) 1.1944(4) 0.0572(12) Uani 1 1 d . . .
H2_2 H 0.8402 0.3824 1.2514 0.069 Uiso 1 1 calc R . .
C3_2 C 0.7455(10) 0.5324(8) 1.1365(4) 0.0559(13) Uani 1 1 d . . .
H3_2 H 0.5883 0.5572 1.1552 0.067 Uiso 1 1 calc R . .
C4_2 C 0.8349(8) 0.5975(6) 1.0500(3) 0.0473(10) Uani 1 1 d . . .
C5_2 C 1.0693(8) 0.5670(6) 1.0245(3) 0.0417(9) Uani 1 1 d . . .
C6_2 C 1.2185(9) 0.4617(6) 1.0827(3) 0.0484(10) Uani 1 1 d . . .
H6_2 H 1.3762 0.4357 1.0651 0.058 Uiso 1 1 calc R . .
C7_2 C 0.6826(8) 0.7096(7) 0.9844(3) 0.0472(10) Uani 1 1 d . . .
H7_2 H 0.5629 0.6594 0.9825 0.057 Uiso 1 1 calc R . .
C8_2 C 0.5686(11) 0.8950(7) 1.0150(4) 0.0579(12) Uani 1 1 d . . .
H8_2 H 0.6594 0.9549 1.0295 0.069 Uiso 1 1 calc R . .
C9_2 C 0.3490(11) 0.9781(8) 1.0225(4) 0.0602(14) Uani 1 1 d . . .
H9A_2 H 0.2538 0.9217 1.0084 0.072 Uiso 1 1 calc R . .
H9B_2 H 0.2877 1.0938 1.0419 0.072 Uiso 1 1 calc R . .
C10_2 C 1.0359(7) 0.6982(6) 0.8784(3) 0.0418(10) Uani 1 1 d . . .
C11_2 C 1.1166(5) 0.7645(4) 0.78587(19) 0.0462(9) Uani 1 1 d GU . .
C12_2 C 0.9651(4) 0.8546(5) 0.7260(2) 0.0560(11) Uani 1 1 d G . .
H12_2 H 0.8090 0.8739 0.7452 0.067 Uiso 1 1 calc R . .
C13_2 C 1.0468(6) 0.9157(5) 0.6376(2) 0.0675(17) Uani 1 1 d G . .
H13_2 H 0.9454 0.9760 0.5975 0.081 Uiso 1 1 calc R . .
C14_2 C 1.2800(6) 0.8868(5) 0.6089(2) 0.0625(13) Uani 1 1 d G . .
H14_2 H 1.3347 0.9277 0.5497 0.075 Uiso 1 1 calc R . .
C15_2 C 1.4315(4) 0.7968(5) 0.6688(2) 0.0670(15) Uani 1 1 d G . .
H15_2 H 1.5876 0.7774 0.6496 0.080 Uiso 1 1 calc R . .
C16_2 C 1.3498(5) 0.7356(4) 0.7573(2) 0.0594(13) Uani 1 1 d GU . .
H16_2 H 1.4512 0.6754 0.7973 0.071 Uiso 1 1 calc R . .


_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_1 C1_1 1.892(5) . ?
O1_1 C10_1 1.367(6) . ?
O1_1 C7_1 1.438(6) . ?
N1_1 C10_1 1.272(6) . ?
N1_1 C5_1 1.395(5) . ?
C1_1 C6_1 1.382(7) . ?
C1_1 C2_1 1.382(8) . ?
C2_1 C3_1 1.368(8) . ?
C3_1 C4_1 1.401(7) . ?
C4_1 C5_1 1.386(6) . ?
C4_1 C7_1 1.510(7) . ?
C5_1 C6_1 1.399(6) . ?
C7_1 C8_1 1.489(7) . ?
C8_1 C9_1 1.281(8) . ?
C10_1 C11_1 1.453(5) . ?
C11_1 C12_1 1.3900 . ?
C11_1 C16_1 1.3900 . ?
C12_1 C13_1 1.3900 . ?
C13_1 C14_1 1.3900 . ?
C14_1 C15_1 1.3900 . ?
C15_1 C16_1 1.3900 . ?
Br2_2 C1_2 1.892(5) . ?
O2_2 C10_2 1.357(5) . ?
O2_2 C7_2 1.445(6) . ?
N2_2 C10_2 1.275(6) . ?
N2_2 C5_2 1.398(6) . ?
C1_2 C2_2 1.339(8) . ?
C1_2 C6_2 1.403(7) . ?
C2_2 C3_2 1.401(8) . ?
C3_2 C4_2 1.397(7) . ?
C4_2 C5_2 1.391(7) . ?
C4_2 C7_2 1.503(7) . ?
C5_2 C6_2 1.401(6) . ?
C7_2 C8_2 1.493(8) . ?
C8_2 C9_2 1.306(9) . ?
C10_2 C11_2 1.453(5) . ?
C11_2 C12_2 1.3900 . ?
C11_2 C16_2 1.3900 . ?
C12_2 C13_2 1.3900 . ?
C13_2 C14_2 1.3900 . ?
C14_2 C15_2 1.3900 . ?
C15_2 C16_2 1.3900 . ?

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
C10_1 O1_1 C7_1 119.9(4) . . ?
C10_1 N1_1 C5_1 117.8(4) . . ?
C6_1 C1_1 C2_1 121.3(4) . . ?
C6_1 C1_1 Br1_1 118.5(4) . . ?
C2_1 C1_1 Br1_1 120.2(4) . . ?
C3_1 C2_1 C1_1 119.3(4) . . ?
C2_1 C3_1 C4_1 120.6(4) . . ?
C5_1 C4_1 C3_1 120.0(4) . . ?
C5_1 C4_1 C7_1 118.1(4) . . ?
C3_1 C4_1 C7_1 121.9(4) . . ?
C4_1 C5_1 N1_1 122.3(4) . . ?
C4_1 C5_1 C6_1 119.2(4) . . ?
N1_1 C5_1 C6_1 118.5(4) . . ?
C1_1 C6_1 C5_1 119.6(4) . . ?
O1_1 C7_1 C8_1 109.0(4) . . ?
O1_1 C7_1 C4_1 110.6(4) . . ?
C8_1 C7_1 C4_1 113.6(4) . . ?
C9_1 C8_1 C7_1 123.9(5) . . ?
N1_1 C10_1 O1_1 125.0(4) . . ?
N1_1 C10_1 C11_1 122.8(4) . . ?
O1_1 C10_1 C11_1 112.2(4) . . ?
C12_1 C11_1 C16_1 120.0 . . ?
C12_1 C11_1 C10_1 121.1(3) . . ?
C16_1 C11_1 C10_1 118.8(3) . . ?
C11_1 C12_1 C13_1 120.0 . . ?
C14_1 C13_1 C12_1 120.0 . . ?
C13_1 C14_1 C15_1 120.0 . . ?
C16_1 C15_1 C14_1 120.0 . . ?
C15_1 C16_1 C11_1 120.0 . . ?
C10_2 O2_2 C7_2 118.9(3) . . ?
C10_2 N2_2 C5_2 117.3(4) . . ?
C2_2 C1_2 C6_2 122.1(5) . . ?
C2_2 C1_2 Br2_2 120.5(4) . . ?
C6_2 C1_2 Br2_2 117.4(4) . . ?
C1_2 C2_2 C3_2 120.6(5) . . ?
C4_2 C3_2 C2_2 118.8(5) . . ?
C5_2 C4_2 C3_2 120.3(4) . . ?
C5_2 C4_2 C7_2 117.9(4) . . ?
C3_2 C4_2 C7_2 121.7(5) . . ?
C4_2 C5_2 N2_2 122.0(4) . . ?
C4_2 C5_2 C6_2 120.0(4) . . ?
N2_2 C5_2 C6_2 117.9(4) . . ?
C5_2 C6_2 C1_2 118.1(4) . . ?
O2_2 C7_2 C8_2 109.2(4) . . ?
O2_2 C7_2 C4_2 109.5(4) . . ?
C8_2 C7_2 C4_2 113.8(4) . . ?
C9_2 C8_2 C7_2 123.9(5) . . ?
N2_2 C10_2 O2_2 124.8(4) . . ?
N2_2 C10_2 C11_2 122.9(4) . . ?
O2_2 C10_2 C11_2 112.3(3) . . ?
C12_2 C11_2 C16_2 120.0 . . ?
C12_2 C11_2 C10_2 121.1(3) . . ?
C16_2 C11_2 C10_2 118.9(3) . . ?
C13_2 C12_2 C11_2 120.0 . . ?
C12_2 C13_2 C14_2 120.0 . . ?
C15_2 C14_2 C13_2 120.0 . . ?
C14_2 C15_2 C16_2 120.0 . . ?
C15_2 C16_2 C11_2 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.972
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.116

_database_code_depnum_ccdc_archive 'CCDC 957091'
