# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 
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data_mo_20180126C_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1829931'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-10-01 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            'C12 H12 Br N O2'
_chemical_formula_weight         282.14

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/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                   6.8559(6)
_cell_length_b                   13.8455(12)
_cell_length_c                   12.3109(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.553(3)
_cell_angle_gamma                90
_cell_volume                     1158.45(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    571(2)
_cell_measurement_reflns_used    7819
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    3.532
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      571(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            12516
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.942
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2244
_reflns_number_gt                1898
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0555P)²+3.3909P] 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         2244
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.71433(8) 0.83576(4) 0.29013(5) 0.0580(2) Uani 1 1 d . . . . .
C1 C 0.2075(7) 0.7160(3) 0.2487(4) 0.0394(11) Uani 1 1 d . . . . .
H1 H 0.1703 0.7600 0.2992 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0877(7) 0.7013(4) 0.1517(4) 0.0463(12) Uani 1 1 d . . . . .
H2 H -0.0280 0.7367 0.1362 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1379(7) 0.6349(4) 0.0774(4) 0.0426(11) Uani 1 1 d . . . . .
H3 H 0.0544 0.6238 0.0128 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3111(6) 0.5850(3) 0.0987(3) 0.0339(9) Uani 1 1 d . . . . .
H4 H 0.3460 0.5405 0.0481 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4352(5) 0.6008(3) 0.1964(3) 0.0237(8) Uani 1 1 d . . . . .
C6 C 0.3833(6) 0.6659(3) 0.2726(3) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.5098(6) 0.6796(3) 0.3811(3) 0.0312(9) Uani 1 1 d . . . . .
C8 C 0.7035(7) 0.6225(3) 0.3931(4) 0.0368(10) Uani 1 1 d . . . . .
C9 C 0.6214(6) 0.5463(3) 0.2142(3) 0.0272(8) Uani 1 1 d . . . . .
C10 C 0.9225(7) 0.5019(4) 0.3314(4) 0.0466(12) Uani 1 1 d . . . . .
H10A H 1.0081 0.5290 0.3917 0.070 Uiso 1 1 calc R U . . .
H10B H 0.9863 0.5038 0.2665 0.070 Uiso 1 1 calc R U . . .
H10C H 0.8930 0.4361 0.3477 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3971(8) 0.6434(4) 0.4779(4) 0.0486(12) Uani 1 1 d . . . . .
H11A H 0.2725 0.6757 0.4740 0.073 Uiso 1 1 calc R U . . .
H11B H 0.4744 0.6576 0.5468 0.073 Uiso 1 1 calc R U . . .
H11C H 0.3762 0.5750 0.4715 0.073 Uiso 1 1 calc R U . . .
C12 C 0.5648(7) 0.7856(3) 0.4015(4) 0.0397(11) Uani 1 1 d . . . . .
H12A H 0.6422 0.7919 0.4729 0.048 Uiso 1 1 calc R U . . .
H12B H 0.4458 0.8234 0.4017 0.048 Uiso 1 1 calc R U . . .
N1 N 0.7395(5) 0.5579(2) 0.3134(3) 0.0286(7) Uani 1 1 d . . . . .
O1 O 0.8195(6) 0.6317(3) 0.4756(3) 0.0684(13) Uani 1 1 d . . . . .
O2 O 0.6725(5) 0.4917(3) 0.1473(3) 0.0497(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
Br1 C12 1.945(5) . ?
C1 C2 1.373(7) . ?
C1 C6 1.388(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 C9 1.475(5) . ?
C6 C7 1.506(6) . ?
C7 C12 1.527(6) . ?
C7 C8 1.536(6) . ?
C7 C11 1.584(7) . ?
C8 O1 1.212(5) . ?
C8 N1 1.374(5) . ?
C9 O2 1.203(5) . ?
C9 N1 1.383(5) . ?
C10 N1 1.467(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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 120.9(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 C9 122.0(3) . . ?
C4 C5 C9 117.7(4) . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 C7 121.0(4) . . ?
C1 C6 C7 120.5(4) . . ?
C6 C7 C12 111.6(3) . . ?
C6 C7 C8 114.2(3) . . ?
C12 C7 C8 106.7(4) . . ?
C6 C7 C11 110.3(4) . . ?
C12 C7 C11 108.3(4) . . ?
C8 C7 C11 105.4(4) . . ?
O1 C8 N1 120.5(4) . . ?
O1 C8 C7 119.4(4) . . ?
N1 C8 C7 120.1(3) . . ?
O2 C9 N1 119.2(4) . . ?
O2 C9 C5 123.0(4) . . ?
N1 C9 C5 117.8(3) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 Br1 111.7(3) . . ?
C7 C12 H12A 109.3 . . ?
Br1 C12 H12A 109.3 . . ?
C7 C12 H12B 109.3 . . ?
Br1 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C8 N1 C9 124.5(3) . . ?
C8 N1 C10 117.8(3) . . ?
C9 N1 C10 117.5(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 1.6(8) . . . . ?
C1 C2 C3 C4 -2.0(8) . . . . ?
C2 C3 C4 C5 0.8(7) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C3 C4 C5 C9 -179.0(4) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
C9 C5 C6 C1 178.6(4) . . . . ?
C4 C5 C6 C7 176.5(4) . . . . ?
C9 C5 C6 C7 -3.8(6) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
C2 C1 C6 C7 -177.7(4) . . . . ?
C5 C6 C7 C12 126.1(4) . . . . ?
C1 C6 C7 C12 -56.4(5) . . . . ?
C5 C6 C7 C8 5.0(6) . . . . ?
C1 C6 C7 C8 -177.5(4) . . . . ?
C5 C6 C7 C11 -113.5(4) . . . . ?
C1 C6 C7 C11 64.0(5) . . . . ?
C6 C7 C8 O1 177.0(5) . . . . ?
C12 C7 C8 O1 53.2(6) . . . . ?
C11 C7 C8 O1 -61.8(6) . . . . ?
C6 C7 C8 N1 -6.5(6) . . . . ?
C12 C7 C8 N1 -130.2(4) . . . . ?
C11 C7 C8 N1 114.7(5) . . . . ?
C6 C5 C9 O2 -177.4(4) . . . . ?
C4 C5 C9 O2 2.3(6) . . . . ?
C6 C5 C9 N1 3.7(6) . . . . ?
C4 C5 C9 N1 -176.6(4) . . . . ?
C6 C7 C12 Br1 -60.9(4) . . . . ?
C8 C7 C12 Br1 64.5(4) . . . . ?
C11 C7 C12 Br1 177.5(3) . . . . ?
O1 C8 N1 C9 -176.3(5) . . . . ?
C7 C8 N1 C9 7.2(7) . . . . ?
O1 C8 N1 C10 -0.6(7) . . . . ?
C7 C8 N1 C10 -177.1(4) . . . . ?
O2 C9 N1 C8 175.5(4) . . . . ?
C5 C9 N1 C8 -5.5(6) . . . . ?
O2 C9 N1 C10 -0.2(6) . . . . ?
C5 C9 N1 C10 178.7(4) . . . . ?

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
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655
C12 H12B O2 0.97 2.51 3.300(6) 138.2 2_655

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.097

