# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BG_1
_database_code_depnum_ccdc_archive 'CCDC 1899501'
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 Br0 N O3'
_chemical_formula_weight         341.35

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.168(2)
_cell_length_b                   21.907(4)
_cell_length_c                   9.858(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.23(3)
_cell_angle_gamma                90.00
_cell_volume                     1919.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2486
_cell_measurement_theta_min      2.829
_cell_measurement_theta_max      25.762

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16173
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         25.762
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3622
_reflns_number_gt                2486
_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       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1546P)²+0.2960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3622
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.2068
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
O2 O 0.1801(2) 0.29658(11) 0.1360(2) 0.0618(6) Uani 1 1 d . . . . .
O1 O 0.2565(2) 0.40233(10) 0.1007(2) 0.0644(7) Uani 1 1 d . . . . .
N1 N 0.6591(3) 0.38839(9) 0.1269(2) 0.0452(6) Uani 1 1 d . . . . .
C16 C 0.5231(3) 0.33713(10) 0.4104(2) 0.0353(6) Uani 1 1 d . . . . .
C9 C 0.6187(3) 0.44466(10) 0.1633(2) 0.0358(6) Uani 1 1 d . . . . .
C11 C 0.4025(3) 0.34400(10) 0.2848(3) 0.0369(6) Uani 1 1 d . . . . .
C8 C 0.4805(3) 0.45122(10) 0.2019(2) 0.0384(6) Uani 1 1 d . . . . .
C19 C 0.7587(3) 0.31700(11) 0.6591(3) 0.0376(6) Uani 1 1 d . . . . .
C17 C 0.6264(3) 0.38357(11) 0.4720(3) 0.0406(6) Uani 1 1 d . . . . .
H17 H 0.6171 0.4220 0.4309 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7390(3) 0.37368(11) 0.5895(3) 0.0415(6) Uani 1 1 d . . . . .
H18 H 0.8049 0.4054 0.6247 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7081(3) 0.49753(11) 0.1601(3) 0.0408(6) Uani 1 1 d . . . . .
C10 C 0.3754(3) 0.39793(11) 0.1946(3) 0.0408(6) Uani 1 1 d . . . . .
C15 C 0.5398(3) 0.28023(11) 0.4834(3) 0.0389(6) Uani 1 1 d . . . . .
C20 C 0.6568(3) 0.27158(11) 0.6062(3) 0.0421(6) Uani 1 1 d . . . . .
H20 H 0.6648 0.2342 0.6523 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3012(3) 0.29459(12) 0.2455(3) 0.0456(7) Uani 1 1 d . . . . .
C33 C 0.8887(3) 0.30779(13) 0.7832(3) 0.0471(7) Uani 1 1 d . . . . .
C7 C 0.4335(3) 0.50794(12) 0.2304(3) 0.0493(7) Uani 1 1 d . . . . .
H7 H 0.3407 0.5122 0.2517 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6558(3) 0.55491(12) 0.1942(3) 0.0525(8) Uani 1 1 d . . . . .
H5 H 0.7141 0.5896 0.1930 0.063 Uiso 1 1 calc R U . . .
C14 C 0.4379(3) 0.23164(12) 0.4321(3) 0.0526(8) Uani 1 1 d . . . . .
H14 H 0.4512 0.1942 0.4779 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3224(3) 0.23899(12) 0.3186(3) 0.0548(8) Uani 1 1 d . . . . .
H13 H 0.2560 0.2069 0.2883 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8430(3) 0.48964(13) 0.1205(3) 0.0536(8) Uani 1 1 d . . . . .
H3 H 0.9060 0.5228 0.1193 0.064 Uiso 1 1 calc R U . . .
C1 C 0.7848(3) 0.38415(13) 0.0879(3) 0.0572(8) Uani 1 1 d . . . . .
H1 H 0.8122 0.3460 0.0608 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5226(4) 0.56000(12) 0.2283(3) 0.0582(8) Uani 1 1 d . . . . .
H6 H 0.4896 0.5980 0.2504 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8815(4) 0.43369(15) 0.0842(4) 0.0630(9) Uani 1 1 d . . . . .
H2 H 0.9708 0.4279 0.0570 0.076 Uiso 1 1 calc R U . . .
O10 O 0.9771(2) 0.34975(10) 0.8257(2) 0.0708(7) Uani 1 1 d . . . . .
C34 C 0.9116(3) 0.24712(14) 0.8541(3) 0.0616(9) Uani 1 1 d . . . . .
H34A H 0.8332 0.2197 0.8082 0.092 Uiso 1 1 calc R U . . .
H34B H 1.0074 0.2308 0.8493 0.092 Uiso 1 1 calc R U . . .
H34C H 0.9089 0.2518 0.9503 0.092 Uiso 1 1 calc R U . . .
H2A H 0.187(4) 0.3319(17) 0.104(4) 0.076(11) Uiso 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
O2 C12 1.345(3) . ?
O2 H2A 0.84(4) . ?
O1 C10 1.248(3) . ?
N1 C1 1.304(3) . ?
N1 C9 1.361(3) . ?
C16 C17 1.421(3) . ?
C16 C15 1.429(3) . ?
C16 C11 1.451(3) . ?
C9 C8 1.417(3) . ?
C9 C4 1.424(3) . ?
C11 C12 1.417(3) . ?
C11 C10 1.463(3) . ?
C8 C7 1.367(3) . ?
C8 C10 1.504(3) . ?
C19 C20 1.377(3) . ?
C19 C18 1.408(3) . ?
C19 C33 1.497(4) . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C4 C3 1.396(4) . ?
C4 C5 1.415(4) . ?
C15 C20 1.419(4) . ?
C15 C14 1.425(3) . ?
C20 H20 0.9300 . ?
C12 C13 1.404(4) . ?
C33 O10 1.229(3) . ?
C33 C34 1.492(4) . ?
C7 C6 1.406(4) . ?
C7 H7 0.9300 . ?
C5 C6 1.349(4) . ?
C5 H5 0.9300 . ?
C14 C13 1.348(4) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C3 C2 1.348(4) . ?
C3 H3 0.9300 . ?
C1 C2 1.408(4) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
C12 O2 H2A 102(2) . . ?
C1 N1 C9 117.4(2) . . ?
C17 C16 C15 115.6(2) . . ?
C17 C16 C11 125.4(2) . . ?
C15 C16 C11 119.0(2) . . ?
N1 C9 C8 118.9(2) . . ?
N1 C9 C4 122.4(2) . . ?
C8 C9 C4 118.7(2) . . ?
C12 C11 C16 117.7(2) . . ?
C12 C11 C10 116.6(2) . . ?
C16 C11 C10 125.6(2) . . ?
C7 C8 C9 119.7(2) . . ?
C7 C8 C10 119.0(2) . . ?
C9 C8 C10 120.8(2) . . ?
C20 C19 C18 117.4(2) . . ?
C20 C19 C33 122.8(2) . . ?
C18 C19 C33 119.8(2) . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
C17 C18 C19 122.1(2) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C3 C4 C5 123.5(2) . . ?
C3 C4 C9 117.4(2) . . ?
C5 C4 C9 119.2(2) . . ?
O1 C10 C11 120.0(2) . . ?
O1 C10 C8 114.1(2) . . ?
C11 C10 C8 125.9(2) . . ?
C20 C15 C14 119.7(2) . . ?
C20 C15 C16 120.8(2) . . ?
C14 C15 C16 119.6(2) . . ?
C19 C20 C15 121.8(2) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
O2 C12 C13 115.0(2) . . ?
O2 C12 C11 123.4(2) . . ?
C13 C12 C11 121.6(2) . . ?
O10 C33 C34 120.1(3) . . ?
O10 C33 C19 120.2(2) . . ?
C34 C33 C19 119.7(2) . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C13 C14 C15 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N1 C1 C2 124.1(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.072

