# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_201806309
_database_code_depnum_ccdc_archive 'CCDC 1858880'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-10-05 downloaded from the CCDC.
;
_audit_creation_date             2018-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 Br N O'
_chemical_formula_sum            'C11 H16 Br N O'
_chemical_formula_weight         258.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15O3N1Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.1817(7)
_cell_length_b                   6.0879(3)
_cell_length_c                   15.7708(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.615(5)
_cell_angle_gamma                90
_cell_volume                     1141.34(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1766
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4380
_cell_measurement_theta_min      3.7130
_shelx_estimated_absorpt_T_max   0.562
_shelx_estimated_absorpt_T_min   0.456
_exptl_absorpt_coefficient_mu    4.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4234
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.026
_diffrn_reflns_theta_max         67.026
_diffrn_reflns_theta_min         3.718
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
  5 omega  -32.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega   58.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega  -31.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   62.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   53.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   48.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   73.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 16 omega   46.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0359777000
_diffrn_orient_matrix_UB_12      0.0646423000
_diffrn_orient_matrix_UB_13      -0.0965134000
_diffrn_orient_matrix_UB_21      0.1231148000
_diffrn_orient_matrix_UB_22      -0.0176966000
_diffrn_orient_matrix_UB_23      -0.0089635000
_diffrn_orient_matrix_UB_31      -0.0185350000
_diffrn_orient_matrix_UB_32      -0.2440343000
_diffrn_orient_matrix_UB_33      -0.0249537000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1726
_reflns_number_total             2035
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0106(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.3246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1059
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.78652(3) 0.43441(7) 0.74277(3) 0.0692(2) Uani 1 1 d . . . . .
C1 C 0.7458(2) 0.7787(5) 0.62022(17) 0.0397(7) Uani 1 1 d . . . . .
H1 H 0.6803 0.7957 0.6408 0.048 Uiso 1 1 calc R . . . .
C2 C 0.8226(2) 0.6177(5) 0.65466(18) 0.0388(6) Uani 1 1 d . . . . .
C3 C 0.9231(2) 0.5834(5) 0.62857(19) 0.0389(7) Uani 1 1 d . . . . .
C4 C 0.9410(2) 0.7220(5) 0.56391(19) 0.0423(7) Uani 1 1 d . . . . .
H4 H 1.0070 0.7054 0.5441 0.051 Uiso 1 1 calc R . . . .
C5 C 0.8665(2) 0.8843(5) 0.52672(19) 0.0412(7) Uani 1 1 d . . . . .
H5 H 0.8830 0.9729 0.4831 0.049 Uiso 1 1 calc R . . . .
C6 C 0.7664(2) 0.9151(4) 0.55490(17) 0.0349(6) Uani 1 1 d . . . . .
C7 C 1.0074(3) 0.4102(5) 0.6675(2) 0.0560(9) Uani 1 1 d . . . . .
H7A H 1.0302 0.4329 0.7291 0.084 Uiso 1 1 calc GR . . . .
H7B H 1.0719 0.4198 0.6420 0.084 Uiso 1 1 calc GR . . . .
H7C H 0.9738 0.2675 0.6564 0.084 Uiso 1 1 calc GR . . . .
C8 C 0.7136(2) 1.2409(5) 0.46092(19) 0.0398(7) Uani 1 1 d . . . . .
H8A H 0.7381 1.1759 0.4121 0.048 Uiso 1 1 calc R . . . .
H8B H 0.7754 1.3269 0.4940 0.048 Uiso 1 1 calc R . . . .
C9 C 0.6133(3) 1.3909(5) 0.4274(2) 0.0434(7) Uani 1 1 d . . . . .
H9A H 0.5501 1.3029 0.3978 0.052 Uiso 1 1 calc R . . . .
H9B H 0.5918 1.4623 0.4763 0.052 Uiso 1 1 calc R . . . .
C10 C 0.6389(3) 1.5640(5) 0.3658(2) 0.0427(7) Uani 1 1 d . . . . .
H10A H 0.6604 1.4919 0.3170 0.051 Uiso 1 1 calc R . . . .
H10B H 0.7026 1.6508 0.3955 0.051 Uiso 1 1 calc R . . . .
C11 C 0.5403(3) 1.7168(5) 0.3316(2) 0.0479(7) Uani 1 1 d . . . . .
H11A H 0.5621 1.8210 0.2917 0.057 Uiso 1 1 calc R . . . .
H11B H 0.4780 1.6309 0.2992 0.057 Uiso 1 1 calc R . . . .
N1 N 0.6847(2) 1.0672(4) 0.51580(17) 0.0405(6) Uani 1 1 d . . . . .
H1A H 0.642(3) 1.102(5) 0.548(2) 0.039(9) Uiso 1 1 d . . . . .
O1 O 0.50347(19) 1.8341(4) 0.39756(17) 0.0516(6) Uani 1 1 d . . . . .
H1B H 0.554(3) 1.896(6) 0.425(3) 0.063(13) Uiso 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 C2 1.907(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.377(4) . ?
C3 C7 1.506(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(4) . ?
C6 N1 1.400(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.524(4) . ?
C8 N1 1.457(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.512(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.522(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 O1 1.413(4) . ?
N1 H1A 0.83(3) . ?
O1 H1B 0.77(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
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 Br1 117.2(2) . . ?
C1 C2 C3 123.7(3) . . ?
C3 C2 Br1 119.1(2) . . ?
C2 C3 C7 123.4(3) . . ?
C4 C3 C2 114.8(3) . . ?
C4 C3 C7 121.8(3) . . ?
C3 C4 H4 118.1 . . ?
C3 C4 C5 123.9(3) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 N1 119.8(3) . . ?
C5 C6 N1 122.3(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.2(2) . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.2(2) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C9 C10 C11 113.3(3) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O1 C11 C10 113.6(3) . . ?
O1 C11 H11A 108.8 . . ?
O1 C11 H11B 108.8 . . ?
C6 N1 C8 120.1(2) . . ?
C6 N1 H1A 112(2) . . ?
C8 N1 H1A 117(2) . . ?
C11 O1 H1B 109(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 H1A O1 0.83(3) 2.17(3) 2.975(3) 164(3) 3_686
O1 H1B N1 0.77(4) 2.16(4) 2.927(4) 173(4) 1_565

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
Br1 C2 C3 C4 179.2(2) . . . . ?
Br1 C2 C3 C7 -1.2(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C7 178.9(3) . . . . ?
C1 C6 N1 C8 167.1(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C6 N1 175.4(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 N1 -175.8(3) . . . . ?
C5 C6 N1 C8 -17.2(4) . . . . ?
C6 C1 C2 Br1 -179.0(2) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C7 C3 C4 C5 -179.5(3) . . . . ?
C8 C9 C10 C11 -179.8(3) . . . . ?
C9 C8 N1 C6 -178.4(3) . . . . ?
C9 C10 C11 O1 59.8(4) . . . . ?
N1 C8 C9 C10 -176.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
