# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AZ756_a
_database_code_depnum_ccdc_archive 'CCDC 1894885'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon-Merceron'
;Institut de Chimie de Toulouse (FR 2599), 118 Route de Narbonne, 31062 Toulouse Cedex 09 (France)
France
;
_audit_update_record             
;
2019-01-31 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O2'
_chemical_formula_weight         252.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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'
'-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                   16.5065(10)
_cell_length_b                   7.0663(4)
_cell_length_c                   21.0475(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2455.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9696
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      28.27

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_T_max  0.7349
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            97445
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3042
_reflns_number_gt                2323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+1.0502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36843(11) 0.7943(2) 0.44443(7) 0.0713(5) Uani 1 1 d . . . . .
O2 O 0.29829(10) 0.5964(3) 0.49988(8) 0.0724(5) Uani 1 1 d . . . . .
N1 N 0.74661(8) 0.63362(19) 0.70761(6) 0.0332(3) Uani 1 1 d . . . . .
N2 N 0.36031(11) 0.6863(3) 0.48976(8) 0.0504(4) Uani 1 1 d . . . . .
C1 C 0.83456(9) 0.6285(3) 0.71214(10) 0.0414(4) Uani 1 1 d . . . . .
H1A H 0.858218 0.677154 0.672678 0.062 Uiso 1 1 calc R U . . .
H1B H 0.852442 0.497813 0.718888 0.062 Uiso 1 1 calc R U . . .
H1C H 0.852238 0.707158 0.747896 0.062 Uiso 1 1 calc R U . . .
C2 C 0.69435(9) 0.6071(2) 0.75789(8) 0.0295(3) Uani 1 1 d . . . . .
C3 C 0.71169(11) 0.5884(2) 0.82252(8) 0.0385(4) Uani 1 1 d . . . . .
H3 H 0.765853 0.593381 0.837693 0.046 Uiso 1 1 calc R U . . .
C4 C 0.64774(12) 0.5626(3) 0.86347(8) 0.0436(4) Uani 1 1 d . . . . .
H4 H 0.657777 0.548069 0.907648 0.052 Uiso 1 1 calc R U . . .
C5 C 0.56809(11) 0.5574(3) 0.84086(8) 0.0405(4) Uani 1 1 d . . . . .
H5 H 0.524839 0.539186 0.870003 0.049 Uiso 1 1 calc R U . . .
C6 C 0.55109(10) 0.5782(2) 0.77699(8) 0.0316(3) Uani 1 1 d . . . . .
H6 H 0.496598 0.576534 0.762484 0.038 Uiso 1 1 calc R U . . .
C7 C 0.61473(9) 0.60183(19) 0.73383(7) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.62125(9) 0.6268(2) 0.66588(7) 0.0266(3) Uani 1 1 d . . . . .
C9 C 0.70255(9) 0.6452(2) 0.65304(8) 0.0316(3) Uani 1 1 d . . . . .
H9 H 0.724860 0.663315 0.611878 0.038 Uiso 1 1 calc R U . . .
C10 C 0.55571(9) 0.6355(2) 0.61940(7) 0.0268(3) Uani 1 1 d . . . . .
C11 C 0.48292(9) 0.5374(2) 0.62917(7) 0.0314(3) Uani 1 1 d . . . . .
H11 H 0.477236 0.459667 0.665733 0.038 Uiso 1 1 calc R U . . .
C12 C 0.41924(10) 0.5513(2) 0.58674(8) 0.0352(4) Uani 1 1 d . . . . .
H12 H 0.370095 0.484705 0.593937 0.042 Uiso 1 1 calc R U . . .
C13 C 0.42865(10) 0.6642(2) 0.53363(7) 0.0358(4) Uani 1 1 d . . . . .
C14 C 0.50025(11) 0.7563(2) 0.52063(7) 0.0365(4) Uani 1 1 d . . . . .
H14 H 0.506133 0.828512 0.482841 0.044 Uiso 1 1 calc R U . . .
C15 C 0.56340(10) 0.7420(2) 0.56341(7) 0.0320(3) Uani 1 1 d . . . . .
H15 H 0.612954 0.805393 0.554799 0.038 Uiso 1 1 calc R U . . .


_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
O1 N2 1.229(2) . ?
O2 N2 1.223(2) . ?
N1 C9 1.362(2) . ?
N1 C2 1.378(2) . ?
N1 C1 1.455(2) . ?
N2 C13 1.466(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.396(2) . ?
C2 C7 1.409(2) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.445(2) . ?
C8 C9 1.375(2) . ?
C8 C10 1.460(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(2) . ?
C10 C15 1.404(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C9 N1 C2 108.76(13) . . ?
C9 N1 C1 126.11(14) . . ?
C2 N1 C1 124.80(14) . . ?
O2 N2 O1 123.28(17) . . ?
O2 N2 C13 118.62(17) . . ?
O1 N2 C13 118.10(18) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.25(15) . . ?
N1 C2 C7 108.14(13) . . ?
C3 C2 C7 122.61(15) . . ?
C4 C3 C2 117.77(16) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 120.79(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.29(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.50(15) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 118.04(14) . . ?
C6 C7 C8 135.51(14) . . ?
C2 C7 C8 106.44(13) . . ?
C9 C8 C7 106.19(13) . . ?
C9 C8 C10 125.99(14) . . ?
C7 C8 C10 127.81(13) . . ?
N1 C9 C8 110.47(14) . . ?
N1 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C11 C10 C15 117.75(14) . . ?
C11 C10 C8 121.07(13) . . ?
C15 C10 C8 121.18(14) . . ?
C12 C11 C10 121.43(15) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.55(16) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 122.01(15) . . ?
C14 C13 N2 119.03(16) . . ?
C12 C13 N2 118.96(16) . . ?
C13 C14 C15 118.94(15) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 121.20(15) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JRV380B_a
_database_code_depnum_ccdc_archive 'CCDC 1894886'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon-Merceron'
;Institut de Chimie de Toulouse (FR 2599), 118 Route de Narbonne, 31062 Toulouse Cedex 09 (France)
France
;
_audit_update_record             
;
2019-01-31 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Br N'
_chemical_formula_weight         286.17

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   7.0113(7)
_cell_length_b                   10.6464(12)
_cell_length_c                   16.842(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1257.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9198
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.27

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.245
_shelx_estimated_absorpt_T_min   0.357
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            29152
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         28.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3131
_reflns_number_gt                2490
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.3751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.014(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.83712(6) 0.20917(4) 0.89944(3) 0.05302(15) Uani 1 1 d . . . . .
N1 N -0.1361(4) 0.3842(3) 0.64266(18) 0.0346(7) Uani 1 1 d . . . . .
C1 C -0.2834(6) 0.4775(4) 0.6289(3) 0.0555(13) Uani 1 1 d . . . . .
H1A H -0.274540 0.508275 0.574207 0.083 Uiso 1 1 calc R U . . .
H1B H -0.266051 0.547797 0.665817 0.083 Uiso 1 1 calc R U . . .
H1C H -0.409043 0.439536 0.637497 0.083 Uiso 1 1 calc R U . . .
C2 C -0.1252(4) 0.2693(3) 0.6057(2) 0.0291(7) Uani 1 1 d . . . . .
C3 C -0.2461(5) 0.2189(4) 0.54840(19) 0.0346(7) Uani 1 1 d . . . . .
H3 H -0.351427 0.265018 0.528198 0.041 Uiso 1 1 calc R U . . .
C4 C -0.2062(5) 0.0989(3) 0.5223(2) 0.0365(8) Uani 1 1 d . . . . .
H4 H -0.284834 0.061424 0.482926 0.044 Uiso 1 1 calc R U . . .
C5 C -0.0514(5) 0.0318(3) 0.5530(2) 0.0367(8) Uani 1 1 d . . . . .
H5 H -0.028650 -0.051293 0.534666 0.044 Uiso 1 1 calc R U . . .
C6 C 0.0686(5) 0.0824(3) 0.6089(2) 0.0326(7) Uani 1 1 d . . . . .
H6 H 0.172890 0.034977 0.628820 0.039 Uiso 1 1 calc R U . . .
C7 C 0.0357(4) 0.2055(3) 0.63636(18) 0.0281(6) Uani 1 1 d . . . . .
C8 C 0.1222(4) 0.2876(3) 0.69361(18) 0.0293(7) Uani 1 1 d . . . . .
C9 C 0.0116(5) 0.3933(3) 0.6953(2) 0.0354(8) Uani 1 1 d . . . . .
H9 H 0.034320 0.463677 0.728586 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2936(5) 0.2683(3) 0.74165(19) 0.0289(7) Uani 1 1 d . . . . .
C11 C 0.4455(5) 0.1942(4) 0.7157(2) 0.0352(8) Uani 1 1 d . . . . .
H11 H 0.437774 0.154190 0.665381 0.042 Uiso 1 1 calc R U . . .
C12 C 0.6077(5) 0.1777(4) 0.7617(2) 0.0399(9) Uani 1 1 d . . . . .
H12 H 0.709973 0.127302 0.742966 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6190(5) 0.2348(3) 0.8345(2) 0.0367(8) Uani 1 1 d . . . . .
C14 C 0.4738(5) 0.3113(4) 0.8618(2) 0.0392(9) Uani 1 1 d . . . . .
H14 H 0.484741 0.352544 0.911590 0.047 Uiso 1 1 calc R U . . .
C15 C 0.3118(5) 0.3272(3) 0.8155(2) 0.0346(8) Uani 1 1 d . . . . .
H15 H 0.211281 0.379077 0.834284 0.042 Uiso 1 1 calc R U . . .


_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 C13 1.900(3) . ?
N1 C9 1.366(5) . ?
N1 C2 1.375(4) . ?
N1 C1 1.452(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.392(5) . ?
C2 C7 1.415(4) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.436(5) . ?
C8 C9 1.367(5) . ?
C8 C10 1.463(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(5) . ?
C10 C15 1.398(5) . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(5) . ?
C14 C15 1.388(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C9 N1 C2 108.3(3) . . ?
C9 N1 C1 126.4(3) . . ?
C2 N1 C1 125.2(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 128.5(3) . . ?
N1 C2 C7 107.8(3) . . ?
C3 C2 C7 123.6(3) . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 117.2(3) . . ?
C6 C7 C8 135.9(3) . . ?
C2 C7 C8 106.8(3) . . ?
C9 C8 C7 106.0(3) . . ?
C9 C8 C10 124.8(3) . . ?
C7 C8 C10 129.2(3) . . ?
N1 C9 C8 111.0(3) . . ?
N1 C9 H9 124.5 . . ?
C8 C9 H9 124.5 . . ?
C11 C10 C15 117.5(3) . . ?
C11 C10 C8 122.2(3) . . ?
C15 C10 C8 120.2(3) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 Br1 119.9(3) . . ?
C14 C13 Br1 119.1(3) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.3(3) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.061

