# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_a60311b
_database_code_depnum_ccdc_archive 'CCDC 1498018'
_audit_update_record             
;
2016-08-07 deposited with the CCDC.
2017-02-10 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            'C21 H15 Br2 N O2'
_chemical_formula_weight         473.16

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                   16.003(5)
_cell_length_b                   7.036(2)
_cell_length_c                   16.456(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.876(4)
_cell_angle_gamma                90
_cell_volume                     1813.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3669
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.59

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    4.486
_shelx_estimated_absorpt_T_min   0.400
_shelx_estimated_absorpt_T_max   0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_T_max  0.746
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9213
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.617
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3554
_reflns_number_gt                2979
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0541P)²+0.8329P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.60501(2) 1.03010(6) 0.39209(2) 0.05116(14) Uani 1 1 d . . . . .
Br2 Br 0.44024(2) 1.24650(4) 0.30850(2) 0.04952(13) Uani 1 1 d . . . . .
N1 N 0.62530(16) 0.9680(4) 0.09456(15) 0.0349(5) Uani 1 1 d D . . . .
H1 H 0.5900(16) 1.052(3) 0.1000(18) 0.030(8) Uiso 1 1 d D . . . .
O1 O 0.50564(15) 1.0955(3) 0.17062(13) 0.0476(6) Uani 1 1 d . . . . .
O2 O 0.74526(15) 0.9238(4) 0.04257(16) 0.0531(6) Uani 1 1 d . . . . .
C1 C 0.58425(16) 0.8152(4) 0.21381(16) 0.0283(5) Uani 1 1 d . . . . .
C2 C 0.62949(17) 0.8125(4) 0.14864(16) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.67870(19) 0.6536(4) 0.13955(18) 0.0371(7) Uani 1 1 d . . . . .
H3 H 0.7078 0.6496 0.0961 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6851(2) 0.5034(4) 0.1931(2) 0.0410(7) Uani 1 1 d . . . . .
H4 H 0.7188 0.3996 0.1860 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6422(2) 0.5039(4) 0.2574(2) 0.0400(7) Uani 1 1 d . . . . .
H5 H 0.6470 0.4017 0.2939 0.048 Uiso 1 1 calc R U . . .
C6 C 0.59210(18) 0.6582(4) 0.26688(18) 0.0357(6) Uani 1 1 d . . . . .
H6 H 0.5626 0.6579 0.3100 0.043 Uiso 1 1 calc R U . . .
C7 C 0.52893(17) 0.9783(4) 0.22475(17) 0.0304(6) Uani 1 1 d . . . . .
C8 C 0.50048(18) 1.0037(4) 0.30874(17) 0.0305(6) Uani 1 1 d . . . . .
C9 C 0.43978(16) 0.8532(4) 0.32845(16) 0.0289(6) Uani 1 1 d . . . . .
C10 C 0.37477(19) 0.7939(5) 0.26505(19) 0.0387(7) Uani 1 1 d . . . . .
H10 H 0.3719 0.8391 0.2114 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3138(2) 0.6678(5) 0.2807(2) 0.0466(8) Uani 1 1 d . . . . .
H11 H 0.2703 0.6280 0.2374 0.056 Uiso 1 1 calc R U . . .
C12 C 0.3170(2) 0.6014(5) 0.3590(2) 0.0467(8) Uani 1 1 d . . . . .
H12 H 0.2751 0.5189 0.3695 0.056 Uiso 1 1 calc R U . . .
C13 C 0.3823(2) 0.6564(5) 0.4226(2) 0.0462(8) Uani 1 1 d . . . . .
H13 H 0.3852 0.6087 0.4758 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4438(2) 0.7827(4) 0.40776(18) 0.0389(7) Uani 1 1 d . . . . .
H14 H 0.4878 0.8202 0.4510 0.047 Uiso 1 1 calc R U . . .
C15 C 0.68227(18) 1.0162(4) 0.04620(17) 0.0337(6) Uani 1 1 d . . . . .
C16 C 0.66293(18) 1.1984(4) -0.00099(16) 0.0321(6) Uani 1 1 d . . . . .
C17 C 0.7311(2) 1.2915(5) -0.02330(18) 0.0388(7) Uani 1 1 d . . . . .
H17 H 0.7855 1.2388 -0.0093 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7195(2) 1.4613(5) -0.0660(2) 0.0485(8) Uani 1 1 d . . . . .
H18 H 0.7661 1.5241 -0.0792 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6386(3) 1.5377(5) -0.0891(2) 0.0496(8) Uani 1 1 d . . . . .
H19 H 0.6304 1.6522 -0.1179 0.060 Uiso 1 1 calc R U . . .
C20 C 0.5704(2) 1.4438(5) -0.0693(2) 0.0483(8) Uani 1 1 d . . . . .
H20 H 0.5157 1.4933 -0.0862 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5821(2) 1.2772(4) -0.02477(19) 0.0402(7) Uani 1 1 d . . . . .
H21 H 0.5354 1.2168 -0.0105 0.048 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 C8 1.942(3) . ?
Br2 C8 1.961(3) . ?
N1 C15 1.371(4) . ?
N1 C2 1.403(4) . ?
N1 H1 0.837(17) . ?
O1 C7 1.215(3) . ?
O2 C15 1.211(4) . ?
C1 C6 1.397(4) . ?
C1 C2 1.412(4) . ?
C1 C7 1.483(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.552(4) . ?
C8 C9 1.517(4) . ?
C9 C10 1.378(4) . ?
C9 C14 1.385(4) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.498(4) . ?
C16 C17 1.385(4) . ?
C16 C21 1.388(4) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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
C15 N1 C2 127.6(2) . . ?
C15 N1 H1 116(2) . . ?
C2 N1 H1 116(2) . . ?
C6 C1 C2 118.0(3) . . ?
C6 C1 C7 121.0(2) . . ?
C2 C1 C7 121.0(2) . . ?
C3 C2 N1 120.8(2) . . ?
C3 C2 C1 118.8(3) . . ?
N1 C2 C1 120.4(2) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
O1 C7 C1 122.5(3) . . ?
O1 C7 C8 118.2(2) . . ?
C1 C7 C8 119.3(2) . . ?
C9 C8 C7 115.4(2) . . ?
C9 C8 Br1 114.35(19) . . ?
C7 C8 Br1 105.79(18) . . ?
C9 C8 Br2 105.82(18) . . ?
C7 C8 Br2 109.43(18) . . ?
Br1 C8 Br2 105.65(13) . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C8 117.8(2) . . ?
C14 C9 C8 122.9(3) . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
O2 C15 N1 123.7(3) . . ?
O2 C15 C16 121.3(3) . . ?
N1 C15 C16 115.0(3) . . ?
C17 C16 C21 118.4(3) . . ?
C17 C16 C15 116.9(3) . . ?
C21 C16 C15 124.7(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

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
C15 N1 C2 C3 -21.1(4) . . . . ?
C15 N1 C2 C1 158.4(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C7 C1 C2 C3 -178.2(3) . . . . ?
C6 C1 C2 N1 -178.7(3) . . . . ?
C7 C1 C2 N1 2.3(4) . . . . ?
N1 C2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C7 C1 C6 C5 179.2(3) . . . . ?
C6 C1 C7 O1 -163.3(3) . . . . ?
C2 C1 C7 O1 15.7(4) . . . . ?
C6 C1 C7 C8 17.7(4) . . . . ?
C2 C1 C7 C8 -163.3(2) . . . . ?
O1 C7 C8 C9 113.3(3) . . . . ?
C1 C7 C8 C9 -67.7(3) . . . . ?
O1 C7 C8 Br1 -119.2(3) . . . . ?
C1 C7 C8 Br1 59.8(3) . . . . ?
O1 C7 C8 Br2 -5.8(3) . . . . ?
C1 C7 C8 Br2 173.2(2) . . . . ?
C7 C8 C9 C10 -41.9(3) . . . . ?
Br1 C8 C9 C10 -164.9(2) . . . . ?
Br2 C8 C9 C10 79.2(3) . . . . ?
C7 C8 C9 C14 142.3(3) . . . . ?
Br1 C8 C9 C14 19.2(3) . . . . ?
Br2 C8 C9 C14 -96.6(3) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C8 C9 C10 C11 -175.2(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
C11 C12 C13 C14 1.5(5) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C10 C9 C14 C13 -0.9(4) . . . . ?
C8 C9 C14 C13 174.9(3) . . . . ?
C2 N1 C15 O2 1.8(5) . . . . ?
C2 N1 C15 C16 -176.2(3) . . . . ?
O2 C15 C16 C17 -22.8(4) . . . . ?
N1 C15 C16 C17 155.3(3) . . . . ?
O2 C15 C16 C21 156.0(3) . . . . ?
N1 C15 C16 C21 -25.9(4) . . . . ?
C21 C16 C17 C18 1.9(4) . . . . ?
C15 C16 C17 C18 -179.3(3) . . . . ?
C16 C17 C18 C19 -1.8(5) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C21 1.8(5) . . . . ?
C19 C20 C21 C16 -1.8(5) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C15 C16 C21 C20 -178.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.837(17) 1.98(2) 2.650(3) 137(3) .

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.083



