# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_A_a
_database_code_depnum_ccdc_archive 'CCDC 1495548'
_audit_update_record             
;
2016-07-23 deposited with the CCDC.
2016-09-07 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            'C H Br N O'
_chemical_formula_weight         122.94

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                   10.1492(6)
_cell_length_b                   17.5386(11)
_cell_length_c                   7.7817(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.257(2)
_cell_angle_gamma                90
_cell_volume                     1336.34(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.444
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11732
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.080
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3082
_reflns_number_gt                2788
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3082
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_restrained_S_all      1.293
_refine_ls_shift/su_max          0.002
_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
Br01 Br 1.01095(3) 0.31799(2) 1.00552(4) 0.01919(17) Uani 1 1 d . . . . .
O002 O 0.7182(2) 0.60510(11) 0.3490(3) 0.0119(4) Uani 1 1 d . . . . .
O003 O 1.0031(2) 0.59029(13) 0.5713(3) 0.0196(5) Uani 1 1 d . . . . .
O004 O 0.7447(2) 0.72894(12) 0.2910(3) 0.0181(5) Uani 1 1 d . . . . .
N005 N 0.6691(2) 0.58033(13) 0.6219(3) 0.0108(5) Uani 1 1 d . . . . .
N006 N 0.5060(2) 0.66824(19) 0.4933(3) 0.0152(6) Uani 1 1 d . . . . .
N007 N 0.4543(2) 0.56732(15) 0.6722(3) 0.0147(5) Uani 1 1 d . . . . .
C008 C 0.5363(3) 0.60704(15) 0.5949(3) 0.0105(5) Uani 1 1 d . . . . .
C009 C 0.8991(3) 0.39996(16) 0.8933(4) 0.0140(6) Uani 1 1 d . . . . .
C00A C 0.7315(3) 0.51742(18) 0.7214(4) 0.0107(5) Uani 1 1 d . . . . .
C00B C 0.8683(3) 0.51195(16) 0.7170(4) 0.0114(5) Uani 1 1 d . . . . .
C00C C 0.6775(3) 0.46344(16) 0.8182(4) 0.0151(6) Uani 1 1 d . . . . .
C00D C 0.7657(3) 0.40519(17) 0.9035(4) 0.0165(6) Uani 1 1 d . . . . .
C00E C 0.8980(3) 0.57454(16) 0.6087(4) 0.0120(5) Uani 1 1 d . . . . .
C00F C 0.9555(3) 0.45375(16) 0.8021(4) 0.0136(6) Uani 1 1 d . . . . .
C00G C 0.7045(3) 0.66679(16) 0.2406(4) 0.0122(6) Uani 1 1 d . . . . .
C00H C 0.7621(3) 0.61823(15) 0.5373(3) 0.0105(5) Uani 1 1 d . . . . .
C00I C 0.2832(3) 0.65980(18) 0.5433(4) 0.0189(6) Uani 1 1 d . . . . .
C00J C 0.3262(3) 0.59546(18) 0.6438(4) 0.0158(6) Uani 1 1 d . . . . .
C00K C 0.6327(3) 0.64515(17) 0.0518(4) 0.0178(6) Uani 1 1 d . . . . .
C00L C 0.3777(3) 0.69506(18) 0.4691(4) 0.0183(6) 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
Br01 C009 1.896(3) . ?
O002 C00G 1.356(3) . ?
O002 C00H 1.434(3) . ?
O003 C00E 1.209(3) . ?
O004 C00G 1.194(3) . ?
N005 C008 1.390(3) . ?
N005 C00A 1.400(4) . ?
N005 C00H 1.447(3) . ?
N006 C008 1.321(4) . ?
N006 C00L 1.351(4) . ?
N007 C008 1.342(3) . ?
N007 C00J 1.353(3) . ?
C009 C00F 1.391(4) . ?
C009 C00D 1.380(4) . ?
C00A C00B 1.401(4) . ?
C00A C00C 1.407(4) . ?
C00B C00F 1.398(4) . ?
C00B C00E 1.463(4) . ?
C00C C00D 1.405(4) . ?
C00E C00H 1.548(4) . ?
C00G C00K 1.507(4) . ?
C00I C00L 1.388(4) . ?
C00I C00J 1.377(4) . ?

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
C00G O002 C00H 117.4(2) . . ?
C008 N005 C00A 129.0(2) . . ?
C008 N005 C00H 120.0(2) . . ?
C00A N005 C00H 111.0(2) . . ?
C008 N006 C00L 115.5(3) . . ?
C008 N007 C00J 114.8(3) . . ?
N006 C008 N007 128.0(2) . . ?
N006 C008 N005 115.3(2) . . ?
N007 C008 N005 116.6(2) . . ?
C00F C009 C00D 121.7(3) . . ?
C00F C009 Br01 118.2(2) . . ?
C00D C009 Br01 120.1(2) . . ?
C00B C00A C00C 119.7(3) . . ?
C00B C00A N005 110.3(2) . . ?
C00C C00A N005 130.0(2) . . ?
C00A C00B C00F 123.1(3) . . ?
C00A C00B C00E 108.6(2) . . ?
C00F C00B C00E 128.3(3) . . ?
C00A C00C C00D 116.9(3) . . ?
C009 C00D C00C 122.3(3) . . ?
O003 C00E C00B 129.7(3) . . ?
O003 C00E C00H 124.0(3) . . ?
C00B C00E C00H 106.2(2) . . ?
C009 C00F C00B 116.3(3) . . ?
O004 C00G O002 123.7(3) . . ?
O004 C00G C00K 125.9(3) . . ?
O002 C00G C00K 110.5(2) . . ?
O002 C00H N005 109.1(2) . . ?
O002 C00H C00E 107.2(2) . . ?
N005 C00H C00E 103.6(2) . . ?
C00L C00I C00J 116.8(3) . . ?
N007 C00J C00I 122.6(3) . . ?
N006 C00L C00I 122.2(3) . . ?

_refine_diff_density_max         0.998
_refine_diff_density_min         -1.070
_refine_diff_density_rms         0.128

