# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_AY61
_database_code_depnum_ccdc_archive 'CCDC 1585913'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-01-19 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         'C12 H10 Br N O'
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12

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'
Br Br -0.2901 2.4595 '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                   12.062(3)
_cell_length_b                   4.0452(9)
_cell_length_c                   21.707(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.12(2)
_cell_angle_gamma                90
_cell_volume                     1059.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      20.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.851
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8904
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.688
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measured_fraction_theta_full 0.800
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_Laue_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 0.800
_reflns_number_total             2179
_reflns_number_gt                1118
_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 (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²] 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         2179
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   0.776
_refine_ls_restrained_S_all      0.776
_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 0.28785(4) 0.31176(10) 0.44140(2) 0.06124(18) Uani 1 1 d . . . . .
C1 C 0.2249(3) 0.4881(9) 0.36886(16) 0.0435(8) Uani 1 1 d . . . . .
C2 C 0.2811(3) 0.4708(9) 0.31419(16) 0.0450(8) Uani 1 1 d . . . . .
H2 H 0.3498 0.3667 0.3133 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2388(3) 0.6034(8) 0.26030(17) 0.0438(9) Uani 1 1 d . . . . .
C4 C 0.1349(3) 0.7575(8) 0.2642(2) 0.0476(9) Uani 1 1 d . . . . .
H4 H 0.1041 0.8510 0.2290 0.057 Uiso 1 1 calc R U . . .
C5 C 0.0774(3) 0.7739(9) 0.3191(2) 0.0515(10) Uani 1 1 d . . . . .
H5 H 0.0089 0.8792 0.3202 0.062 Uiso 1 1 calc R U . . .
C6 C 0.1199(3) 0.6367(9) 0.37218(18) 0.0452(9) Uani 1 1 d . . . . .
C7 C 0.2971(3) 0.5785(9) 0.20018(17) 0.0468(9) Uani 1 1 d . . . . .
C8 C 0.4021(3) 0.4445(10) 0.19504(19) 0.0569(10) Uani 1 1 d . . . . .
H8 H 0.4386 0.3638 0.2297 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4520(4) 0.4317(11) 0.1380(2) 0.0693(12) Uani 1 1 d . . . . .
H9 H 0.5221 0.3389 0.1336 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3977(4) 0.5560(12) 0.0885(2) 0.0700(12) Uani 1 1 d . . . . .
H10 H 0.4304 0.5533 0.0497 0.084 Uiso 1 1 calc R U . . .
C11 C 0.2949(4) 0.6842(11) 0.0963(2) 0.0696(12) Uani 1 1 d . . . . .
H11 H 0.2578 0.7656 0.0619 0.083 Uiso 1 1 calc R U . . .
C12 C -0.0396(4) 0.7764(10) 0.4307(2) 0.0664(12) Uani 1 1 d . . . . .
H12A H -0.0351 1.0098 0.4230 0.100 Uiso 1 1 calc R U . . .
H12B H -0.0704 0.7393 0.4709 0.100 Uiso 1 1 calc R U . . .
H12C H -0.0863 0.6753 0.4002 0.100 Uiso 1 1 calc R U . . .
N1 N 0.2441(3) 0.6997(8) 0.15102(17) 0.0620(9) Uani 1 1 d . . . . .
O1 O 0.0683(2) 0.6355(6) 0.42775(13) 0.0565(7) 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
Br1 C1 1.887(3) . ?
C1 C2 1.369(5) . ?
C1 C6 1.404(5) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(5) . ?
C3 C7 1.487(5) . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 O1 1.359(5) . ?
C7 N1 1.336(5) . ?
C7 C8 1.382(5) . ?
C8 C9 1.379(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.355(6) . ?
C10 H10 0.9300 . ?
C11 N1 1.339(6) . ?
C11 H11 0.9300 . ?
C12 O1 1.422(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C2 C1 C6 121.0(3) . . ?
C2 C1 Br1 120.3(3) . . ?
C6 C1 Br1 118.7(3) . . ?
C1 C2 C3 122.0(3) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C7 122.8(3) . . ?
C4 C3 C7 120.5(3) . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
O1 C6 C5 125.0(3) . . ?
O1 C6 C1 117.4(3) . . ?
C5 C6 C1 117.6(4) . . ?
N1 C7 C8 121.1(4) . . ?
N1 C7 C3 116.7(3) . . ?
C8 C7 C3 122.2(4) . . ?
C9 C8 C7 119.3(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 118.9(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.3(4) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 N1 C11 118.2(4) . . ?
C6 O1 C12 117.4(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
C6 C1 C2 C3 1.4(5) . . . . ?
Br1 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C7 -178.2(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C7 C3 C4 C5 177.8(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 O1 -178.7(3) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C2 C1 C6 O1 178.2(3) . . . . ?
Br1 C1 C6 O1 -1.9(4) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
Br1 C1 C6 C5 177.8(3) . . . . ?
C2 C3 C7 N1 176.1(3) . . . . ?
C4 C3 C7 N1 -2.0(5) . . . . ?
C2 C3 C7 C8 -5.4(5) . . . . ?
C4 C3 C7 C8 176.4(3) . . . . ?
N1 C7 C8 C9 -1.0(6) . . . . ?
C3 C7 C8 C9 -179.4(4) . . . . ?
C7 C8 C9 C10 1.1(7) . . . . ?
C8 C9 C10 C11 -1.1(7) . . . . ?
C9 C10 C11 N1 1.1(7) . . . . ?
C8 C7 N1 C11 0.8(6) . . . . ?
C3 C7 N1 C11 179.3(3) . . . . ?
C10 C11 N1 C7 -0.9(7) . . . . ?
C5 C6 O1 C12 2.4(5) . . . . ?
C1 C6 O1 C12 -178.0(3) . . . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.063



