# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_No2-a
_database_code_depnum_ccdc_archive 'CCDC 1457941'
_audit_update_record             
;
2016-03-05 deposited with the CCDC.
2016-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXTL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Br N2 O3'
_chemical_formula_sum            'C16 H11 Br N2 O3'
_chemical_formula_weight         359.18

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.593(3)
_cell_length_b                   11.744(4)
_cell_length_c                   16.592(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.277(7)
_cell_angle_gamma                90.00
_cell_volume                     1460.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2375
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5047
_exptl_absorpt_correction_T_max  0.6928
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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            8870
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.04
_reflns_number_total             2875
_reflns_number_gt                1697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0373P)²+0.2561P] 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_number_reflns         2875
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C1 C 0.9500(5) 0.5709(3) 0.3047(2) 0.0484(9) Uani 1 1 d . . .
O1 O 0.8505(3) 0.6531(2) 0.29228(16) 0.0625(7) Uani 1 1 d . . .
C2 C 1.1326(5) 0.5868(3) 0.3544(2) 0.0467(8) Uani 1 1 d . . .
C3 C 1.1465(5) 0.6570(3) 0.4224(2) 0.0587(10) Uani 1 1 d . . .
H3 H 1.0419 0.6899 0.4371 0.070 Uiso 1 1 calc R . .
C4 C 1.3096(5) 0.6798(3) 0.4687(2) 0.0605(10) Uani 1 1 d . . .
H4 H 1.3180 0.7268 0.5158 0.073 Uiso 1 1 calc R . .
C5 C 1.4600(5) 0.6337(3) 0.4459(2) 0.0500(9) Uani 1 1 d . . .
C6 C 1.4516(5) 0.5674(3) 0.3774(2) 0.0576(10) Uani 1 1 d . . .
H6 H 1.5576 0.5378 0.3619 0.069 Uiso 1 1 calc R . .
N1 N 1.6350(4) 0.6562(3) 0.4972(2) 0.0619(9) Uani 1 1 d . . .
O2 O 1.7645(4) 0.6045(3) 0.48122(18) 0.0827(9) Uani 1 1 d . . .
O3 O 1.6401(4) 0.7224(3) 0.55463(19) 0.0883(10) Uani 1 1 d . . .
N2 N 0.9030(4) 0.4652(2) 0.27350(17) 0.0505(8) Uani 1 1 d . . .
C7 C 1.2885(5) 0.5442(3) 0.3316(2) 0.0559(10) Uani 1 1 d . . .
H7 H 1.2819 0.4986 0.2839 0.067 Uiso 1 1 calc R . .
C8 C 0.9914(5) 0.3589(3) 0.3068(2) 0.0634(11) Uani 1 1 d . . .
H8A H 1.0836 0.3773 0.3543 0.076 Uiso 1 1 calc R . .
H8B H 1.0512 0.3225 0.2647 0.076 Uiso 1 1 calc R . .
C9 C 0.8605(6) 0.2782(3) 0.3325(2) 0.0667(11) Uani 1 1 d . . .
H9 H 0.9001 0.2236 0.3737 0.080 Uiso 1 1 calc R . .
C10 C 0.6898(6) 0.2806(3) 0.2993(2) 0.0626(10) Uani 1 1 d . . .
H10 H 0.6088 0.2287 0.3177 0.075 Uiso 1 1 calc R . .
C11 C 0.6244(5) 0.3621(3) 0.2348(2) 0.0502(9) Uani 1 1 d . . .
C12 C 0.4562(5) 0.3533(3) 0.1876(2) 0.0556(10) Uani 1 1 d . . .
H12 H 0.3782 0.2931 0.1968 0.067 Uiso 1 1 calc R . .
C13 C 0.4037(5) 0.4325(3) 0.1277(2) 0.0544(9) Uani 1 1 d . . .
Br1 Br 0.16572(6) 0.42915(4) 0.06897(3) 0.0856(2) Uani 1 1 d . . .
C14 C 0.5174(5) 0.5178(3) 0.1100(2) 0.0557(10) Uani 1 1 d . . .
H14 H 0.4808 0.5692 0.0663 0.067 Uiso 1 1 calc R . .
C15 C 0.6848(5) 0.5272(3) 0.1568(2) 0.0566(10) Uani 1 1 d . . .
H15 H 0.7637 0.5858 0.1456 0.068 Uiso 1 1 calc R . .
C16 C 0.7376(5) 0.4512(3) 0.2201(2) 0.0485(9) Uani 1 1 d . . .


_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
C1 O1 1.223(4) . ?
C1 N2 1.370(4) . ?
C1 C2 1.506(5) . ?
C2 C3 1.387(5) . ?
C2 C7 1.393(5) . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(5) . ?
C5 N1 1.482(5) . ?
C6 C7 1.372(5) . ?
C6 H6 0.9500 . ?
N1 O2 1.221(4) . ?
N1 O3 1.226(4) . ?
N2 C16 1.425(4) . ?
N2 C8 1.482(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.484(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.324(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 C16 1.400(5) . ?
C12 C13 1.373(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(5) . ?
C13 Br1 1.910(4) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(5) . ?
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
O1 C1 N2 122.4(3) . . ?
O1 C1 C2 118.9(3) . . ?
N2 C1 C2 118.7(3) . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 117.5(3) . . ?
C7 C2 C1 123.7(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 N1 119.7(3) . . ?
C4 C5 N1 118.8(3) . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
O2 N1 O3 124.0(3) . . ?
O2 N1 C5 117.8(4) . . ?
O3 N1 C5 118.2(3) . . ?
C1 N2 C16 119.3(3) . . ?
C1 N2 C8 123.2(3) . . ?
C16 N2 C8 115.8(3) . . ?
C6 C7 C2 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N2 C8 C9 111.2(3) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 121.5(4) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C16 119.4(3) . . ?
C12 C11 C10 122.4(3) . . ?
C16 C11 C10 118.1(3) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 Br1 119.7(3) . . ?
C14 C13 Br1 118.5(3) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 N2 121.0(3) . . ?
C11 C16 N2 118.8(3) . . ?

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 40.3(5) . . . . ?
N2 C1 C2 C3 -141.1(3) . . . . ?
O1 C1 C2 C7 -133.2(4) . . . . ?
N2 C1 C2 C7 45.4(5) . . . . ?
C7 C2 C3 C4 -3.2(6) . . . . ?
C1 C2 C3 C4 -177.0(3) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C3 C4 C5 N1 -178.5(3) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
N1 C5 C6 C7 178.0(3) . . . . ?
C6 C5 N1 O2 -7.6(5) . . . . ?
C4 C5 N1 O2 172.1(3) . . . . ?
C6 C5 N1 O3 174.8(3) . . . . ?
C4 C5 N1 O3 -5.5(5) . . . . ?
O1 C1 N2 C16 4.4(5) . . . . ?
C2 C1 N2 C16 -174.2(3) . . . . ?
O1 C1 N2 C8 -160.3(3) . . . . ?
C2 C1 N2 C8 21.1(5) . . . . ?
C5 C6 C7 C2 -0.4(6) . . . . ?
C3 C2 C7 C6 2.7(5) . . . . ?
C1 C2 C7 C6 176.2(3) . . . . ?
C1 N2 C8 C9 122.4(4) . . . . ?
C16 N2 C8 C9 -42.8(4) . . . . ?
N2 C8 C9 C10 25.8(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 167.1(4) . . . . ?
C9 C10 C11 C16 -12.2(5) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 3.3(5) . . . . ?
C11 C12 C13 Br1 -174.5(2) . . . . ?
C12 C13 C14 C15 -3.4(5) . . . . ?
Br1 C13 C14 C15 174.4(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 C11 2.5(5) . . . . ?
C14 C15 C16 N2 -174.5(3) . . . . ?
C12 C11 C16 C15 -2.6(5) . . . . ?
C10 C11 C16 C15 176.8(3) . . . . ?
C12 C11 C16 N2 174.4(3) . . . . ?
C10 C11 C16 N2 -6.2(5) . . . . ?
C1 N2 C16 C15 45.6(5) . . . . ?
C8 N2 C16 C15 -148.6(3) . . . . ?
C1 N2 C16 C11 -131.4(3) . . . . ?
C8 N2 C16 C11 34.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.061
