# 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. 
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#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1945647'
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Br N O'
_chemical_formula_weight         316.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.304(3)
_cell_length_b                   5.8888(12)
_cell_length_c                   16.007(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.59(3)
_cell_angle_gamma                90
_cell_volume                     1382.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3506
_cell_measurement_theta_min      2.1778
_cell_measurement_theta_max      27.9103

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.964
_shelx_estimated_absorpt_T_min   0.589
_shelx_estimated_absorpt_T_max   0.717
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5159
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14182
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.624
_diffrn_reflns_theta_max         27.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3309
_reflns_number_gt                2591
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.6844P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0337(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3309
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 0.91105(2) 0.07856(5) 0.83657(2) 0.03429(14) Uani 1 1 d . . . . .
O1 O 0.73425(12) 0.8403(3) 0.51156(12) 0.0250(4) Uani 1 1 d . . . . .
N1 N 0.88682(15) 0.7289(4) 0.53563(14) 0.0234(5) Uani 1 1 d . . . . .
C1 C 0.81812(17) 0.8513(4) 0.49796(16) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.81567(17) 1.0292(4) 0.43399(16) 0.0213(5) Uani 1 1 d . . . . .
C3 C 0.88439(19) 1.1115(5) 0.40107(18) 0.0286(6) Uani 1 1 d . . . . .
H3 H 0.943471 1.045351 0.417270 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8638(2) 1.2925(5) 0.34406(18) 0.0347(7) Uani 1 1 d . . . . .
H4 H 0.909501 1.351851 0.320636 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7773(2) 1.3898(5) 0.32019(19) 0.0334(7) Uani 1 1 d . . . . .
H5 H 0.764760 1.514043 0.280680 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7094(2) 1.3071(5) 0.35357(18) 0.0287(6) Uani 1 1 d . . . . .
H6 H 0.650337 1.373263 0.337540 0.034 Uiso 1 1 calc R U . . .
C7 C 0.72967(18) 1.1265(4) 0.41058(16) 0.0215(6) Uani 1 1 d . . . . .
C8 C 0.67197(17) 1.0080(5) 0.45938(17) 0.0229(6) Uani 1 1 d . . . . .
C9 C 0.59124(19) 0.8828(5) 0.4010(2) 0.0314(7) Uani 1 1 d . . . . .
H9A H 0.612323 0.778072 0.363252 0.047 Uiso 1 1 calc R U . . .
H9B H 0.548500 0.992263 0.364966 0.047 Uiso 1 1 calc R U . . .
H9C H 0.560550 0.796861 0.436853 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6448(2) 1.1674(5) 0.52272(19) 0.0339(7) Uani 1 1 d . . . . .
H10A H 0.614686 1.080357 0.558776 0.051 Uiso 1 1 calc R U . . .
H10B H 0.602904 1.283231 0.489922 0.051 Uiso 1 1 calc R U . . .
H10C H 0.699432 1.241051 0.560215 0.051 Uiso 1 1 calc R U . . .
C11 C 0.88420(17) 0.5758(4) 0.60273(17) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.93497(19) 0.3764(5) 0.60965(18) 0.0260(6) Uani 1 1 d . . . . .
H12 H 0.965856 0.343934 0.567302 0.031 Uiso 1 1 calc R U . . .
C13 C 0.94101(19) 0.2255(5) 0.67714(18) 0.0274(6) Uani 1 1 d . . . . .
H13 H 0.974361 0.088146 0.680378 0.033 Uiso 1 1 calc R U . . .
C14 C 0.89813(18) 0.2765(5) 0.73972(17) 0.0246(6) Uani 1 1 d . . . . .
C15 C 0.84797(19) 0.4730(5) 0.73523(18) 0.0271(6) Uani 1 1 d . . . . .
H15 H 0.818615 0.506038 0.778706 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8409(2) 0.6212(5) 0.66672(18) 0.0281(6) Uani 1 1 d . . . . .
H16 H 0.806079 0.756263 0.663131 0.034 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 C14 1.904(3) . ?
O1 C1 1.363(3) . ?
O1 C8 1.458(3) . ?
N1 C1 1.275(3) . ?
N1 C11 1.412(3) . ?
C1 C2 1.458(4) . ?
C2 C7 1.385(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.507(4) . ?
C8 C9 1.512(4) . ?
C8 C10 1.524(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.395(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 H16 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
C1 O1 C8 111.57(19) . . ?
C1 N1 C11 121.5(2) . . ?
N1 C1 O1 125.7(2) . . ?
N1 C1 C2 126.2(2) . . ?
O1 C1 C2 108.0(2) . . ?
C7 C2 C3 121.1(3) . . ?
C7 C2 C1 108.6(2) . . ?
C3 C2 C1 130.2(2) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 118.4(3) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 C8 130.3(3) . . ?
C2 C7 C8 108.7(2) . . ?
O1 C8 C7 103.1(2) . . ?
O1 C8 C9 108.0(2) . . ?
C7 C8 C9 113.7(2) . . ?
O1 C8 C10 107.1(2) . . ?
C7 C8 C10 111.8(2) . . ?
C9 C8 C10 112.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 N1 117.5(2) . . ?
C16 C11 N1 124.0(2) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 Br1 119.9(2) . . ?
C15 C14 Br1 118.9(2) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 121.1(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?

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
C11 N1 C1 O1 -5.1(4) . . . . ?
C11 N1 C1 C2 173.9(2) . . . . ?
C8 O1 C1 N1 178.6(2) . . . . ?
C8 O1 C1 C2 -0.6(3) . . . . ?
N1 C1 C2 C7 -178.3(2) . . . . ?
O1 C1 C2 C7 0.9(3) . . . . ?
N1 C1 C2 C3 -2.0(5) . . . . ?
O1 C1 C2 C3 177.2(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -176.2(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
C5 C6 C7 C8 177.3(3) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C1 C2 C7 C6 177.1(2) . . . . ?
C3 C2 C7 C8 -177.6(2) . . . . ?
C1 C2 C7 C8 -0.8(3) . . . . ?
C1 O1 C8 C7 0.1(3) . . . . ?
C1 O1 C8 C9 120.7(2) . . . . ?
C1 O1 C8 C10 -118.0(2) . . . . ?
C6 C7 C8 O1 -177.2(3) . . . . ?
C2 C7 C8 O1 0.5(3) . . . . ?
C6 C7 C8 C9 66.2(4) . . . . ?
C2 C7 C8 C9 -116.2(2) . . . . ?
C6 C7 C8 C10 -62.5(4) . . . . ?
C2 C7 C8 C10 115.2(2) . . . . ?
C1 N1 C11 C12 147.4(3) . . . . ?
C1 N1 C11 C16 -38.6(4) . . . . ?
C16 C11 C12 C13 1.2(4) . . . . ?
N1 C11 C12 C13 175.5(2) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 C15 1.2(4) . . . . ?
C12 C13 C14 Br1 -176.7(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
Br1 C14 C15 C16 177.8(2) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
N1 C11 C16 C15 -174.0(3) . . . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.089

