# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_140825lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1039307'
_audit_update_record             
;
2014-12-15 deposited with the CCDC.
2015-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Br N O'
_chemical_formula_weight         268.15

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.8904(6)
_cell_length_b                   13.0832(9)
_cell_length_c                   19.2524(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2239.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4476
_cell_measurement_theta_min      3.1141
_cell_measurement_theta_max      26.3332

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.644
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            15606
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2295
_reflns_number_gt                1852
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0184P)²+2.0411P] 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         2295
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0581
_refine_ls_wR_factor_gt          0.0518
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Br1 Br 0.20422(3) 0.37907(2) 0.04379(2) 0.02651(9) Uani 1 1 d . . . . .
O1 O 0.1391(2) 0.30593(13) 0.33103(7) 0.0287(4) Uani 1 1 d . . . . .
N1 N 0.07388(19) 0.58537(15) 0.32032(9) 0.0183(4) Uani 1 1 d . . . . .
C1 C 0.2068(3) 0.37358(19) 0.44176(11) 0.0275(5) Uani 1 1 d . . . . .
H5 H 0.1337 0.3923 0.4784 0.033 Uiso 1 1 calc R U . . .
H1 H 0.3067 0.3629 0.4634 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2144(2) 0.45640(18) 0.38560(10) 0.0180(5) Uani 1 1 d . . . . .
H4 H 0.3032 0.5020 0.3931 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2331(2) 0.39384(18) 0.31975(11) 0.0195(5) Uani 1 1 d . . . . .
H13 H 0.3403 0.3719 0.3148 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1822(2) 0.44642(17) 0.25455(10) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.2146(2) 0.40069(17) 0.19108(10) 0.0173(5) Uani 1 1 d . . . . .
H11 H 0.2691 0.3383 0.1897 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1673(2) 0.44613(19) 0.13006(10) 0.0183(5) Uani 1 1 d . . . . .
C7 C 0.0934(2) 0.53832(19) 0.13109(11) 0.0209(5) Uani 1 1 d . . . . .
H2 H 0.0646 0.5701 0.0888 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1556(3) 0.2776(2) 0.40266(11) 0.0289(6) Uani 1 1 d . . . . .
H14 H 0.2314 0.2226 0.4075 0.035 Uiso 1 1 calc R U . . .
H3 H 0.0587 0.2527 0.4215 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1040(2) 0.53920(17) 0.25700(10) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.0706(2) 0.51827(18) 0.38071(11) 0.0187(5) Uani 1 1 d . . . . .
H7 H -0.0165 0.4714 0.3772 0.022 Uiso 1 1 calc R U . . .
H6 H 0.0584 0.5597 0.4234 0.022 Uiso 1 1 calc R U . . .
C11 C -0.0310(3) 0.67094(19) 0.32204(12) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.0056 0.7255 0.2915 0.038 Uiso 1 1 calc R U . . .
H10 H -0.0390 0.6968 0.3697 0.038 Uiso 1 1 calc R U . . .
H9 H -0.1301 0.6480 0.3061 0.038 Uiso 1 1 calc R U . . .
C12 C 0.0609(2) 0.58489(19) 0.19392(11) 0.0201(5) Uani 1 1 d . . . . .
H12 H 0.0090 0.6483 0.1944 0.024 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 C6 1.907(2) . ?
O1 C8 1.436(3) . ?
O1 C3 1.438(3) . ?
N1 C9 1.387(3) . ?
N1 C10 1.457(3) . ?
N1 C11 1.457(3) . ?
C1 C2 1.532(3) . ?
C1 C8 1.533(3) . ?
C1 H5 0.9900 . ?
C1 H1 0.9900 . ?
C2 C10 1.516(3) . ?
C2 C3 1.518(3) . ?
C2 H4 1.0000 . ?
C3 C4 1.501(3) . ?
C3 H13 1.0000 . ?
C4 C5 1.391(3) . ?
C4 C9 1.400(3) . ?
C5 C6 1.382(3) . ?
C5 H11 0.9500 . ?
C6 C7 1.374(3) . ?
C7 C12 1.385(3) . ?
C7 H2 0.9500 . ?
C8 H14 0.9900 . ?
C8 H3 0.9900 . ?
C9 C12 1.407(3) . ?
C10 H7 0.9900 . ?
C10 H6 0.9900 . ?
C11 H8 0.9800 . ?
C11 H10 0.9800 . ?
C11 H9 0.9800 . ?
C12 H12 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
C8 O1 C3 106.99(17) . . ?
C9 N1 C10 116.30(19) . . ?
C9 N1 C11 118.55(18) . . ?
C10 N1 C11 115.58(17) . . ?
C2 C1 C8 104.23(17) . . ?
C2 C1 H5 110.9 . . ?
C8 C1 H5 110.9 . . ?
C2 C1 H1 110.9 . . ?
C8 C1 H1 110.9 . . ?
H5 C1 H1 108.9 . . ?
C10 C2 C3 109.18(17) . . ?
C10 C2 C1 112.61(18) . . ?
C3 C2 C1 102.29(19) . . ?
C10 C2 H4 110.8 . . ?
C3 C2 H4 110.8 . . ?
C1 C2 H4 110.8 . . ?
O1 C3 C4 108.51(17) . . ?
O1 C3 C2 103.97(17) . . ?
C4 C3 C2 114.72(19) . . ?
O1 C3 H13 109.8 . . ?
C4 C3 H13 109.8 . . ?
C2 C3 H13 109.8 . . ?
C5 C4 C9 120.36(19) . . ?
C5 C4 C3 118.37(19) . . ?
C9 C4 C3 121.27(19) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H11 120.0 . . ?
C4 C5 H11 120.0 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 Br1 119.93(16) . . ?
C5 C6 Br1 119.35(18) . . ?
C6 C7 C12 119.9(2) . . ?
C6 C7 H2 120.0 . . ?
C12 C7 H2 120.0 . . ?
O1 C8 C1 106.88(19) . . ?
O1 C8 H14 110.3 . . ?
C1 C8 H14 110.3 . . ?
O1 C8 H3 110.3 . . ?
C1 C8 H3 110.3 . . ?
H14 C8 H3 108.6 . . ?
N1 C9 C4 120.20(19) . . ?
N1 C9 C12 121.4(2) . . ?
C4 C9 C12 118.3(2) . . ?
N1 C10 C2 110.75(17) . . ?
N1 C10 H7 109.5 . . ?
C2 C10 H7 109.5 . . ?
N1 C10 H6 109.5 . . ?
C2 C10 H6 109.5 . . ?
H7 C10 H6 108.1 . . ?
N1 C11 H8 109.5 . . ?
N1 C11 H10 109.5 . . ?
H8 C11 H10 109.5 . . ?
N1 C11 H9 109.5 . . ?
H8 C11 H9 109.5 . . ?
H10 C11 H9 109.5 . . ?
C7 C12 C9 120.7(2) . . ?
C7 C12 H12 119.7 . . ?
C9 C12 H12 119.7 . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

