# 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. 
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data_vbchem114_a
_database_code_depnum_ccdc_archive 'CCDC 1433055'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2016-02-18 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.9523(11)
_cell_length_b                   10.8955(15)
_cell_length_c                   13.2918(18)
_cell_angle_alpha                83.854(10)
_cell_angle_beta                 89.882(9)
_cell_angle_gamma                89.928(9)
_cell_volume                     1289.0(3)
_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    2.534
_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    12.492
_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            41097
_diffrn_reflns_av_unetI/netI     0.3056
_diffrn_reflns_av_R_equivalents  0.3862
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.541
_diffrn_reflns_theta_max         28.893
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6642
_reflns_number_gt                2552
_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+0.6035P] 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         6642
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3393
_refine_ls_R_factor_gt           0.1522
_refine_ls_wR_factor_ref         0.3295
_refine_ls_wR_factor_gt          0.2666
_refine_ls_goodness_of_fit_ref   1.360
_refine_ls_restrained_S_all      1.360
_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 0.60373(15) 0.69556(13) 0.83171(11) 0.0499(5) Uani 1 1 d . . . . .
Br2 Br 1.10337(15) 0.80467(14) 0.66864(11) 0.0505(5) Uani 1 1 d . . . . .
O1 O -0.0566(9) 0.6547(9) 0.9647(7) 0.054(3) Uani 1 1 d . . . . .
O2 O 0.4432(9) 0.8452(9) 0.5356(7) 0.050(3) Uani 1 1 d . . . . .
C26 C 0.8119(11) 0.9189(10) 0.5820(8) 0.023(2) Uani 1 1 d . . . . .
H26 H 0.8555 0.8646 0.5412 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4128(11) 0.4930(10) 0.8806(8) 0.025(3) Uani 1 1 d . . . . .
C24 C 0.6668(11) 0.9046(10) 0.5990(8) 0.023(2) Uani 1 1 d . . . . .
C27 C 0.9102(11) 1.0081(10) 0.6188(8) 0.021(2) Uani 1 1 d . . . . .
N2 N 0.5301(11) 1.0311(11) 0.7221(9) 0.053(3) Uani 1 1 d . . . . .
C10 C 0.3119(12) 0.5820(10) 0.9171(8) 0.026(3) Uani 1 1 d . . . . .
H10 H 0.3543 0.6367 0.9580 0.032 Uiso 1 1 calc R U . . .
C28 C 1.0506(12) 0.9714(10) 0.6576(8) 0.026(3) Uani 1 1 d . . . . .
C1 C 0.1361(12) 0.7952(11) 0.9803(8) 0.029(3) Uani 1 1 d . . . . .
C6 C 0.2473(12) 0.8604(11) 0.9264(9) 0.035(3) Uani 1 1 d . . . . .
H6 H 0.2845 0.8330 0.8673 0.042 Uiso 1 1 calc R U . . .
C25 C 0.5913(13) 0.9773(13) 0.6661(10) 0.040(3) Uani 1 1 d . . . . .
C7 C 0.0678(13) 0.6825(11) 0.9478(9) 0.035(3) Uani 1 1 d . . . . .
C8 C 0.1675(11) 0.5957(10) 0.9001(8) 0.022(2) Uani 1 1 d . . . . .
C12 C 0.5515(12) 0.5278(10) 0.8437(8) 0.026(3) Uani 1 1 d . . . . .
N1 N 0.0323(12) 0.4719(12) 0.7769(10) 0.057(3) Uani 1 1 d . . . . .
C16 C 0.3702(14) 0.3706(11) 0.8868(9) 0.037(3) Uani 1 1 d . . . . .
H16 H 0.2781 0.3447 0.9136 0.044 Uiso 1 1 calc R U . . .
C29 C 1.1484(13) 1.0531(13) 0.6902(9) 0.037(3) Uani 1 1 d . . . . .
H29 H 1.2417 1.0275 0.7150 0.045 Uiso 1 1 calc R U . . .
C9 C 0.0938(14) 0.5231(12) 0.8352(11) 0.041(3) Uani 1 1 d . . . . .
C32 C 0.8720(14) 1.1297(12) 0.6149(9) 0.037(3) Uani 1 1 d . . . . .
H32 H 0.7799 1.1566 0.5887 0.044 Uiso 1 1 calc R U . . .
C18 C 0.7479(13) 0.6409(12) 0.5726(9) 0.038(3) Uani 1 1 d . . . . .
H18 H 0.7876 0.6690 0.6305 0.046 Uiso 1 1 calc R U . . .
C23 C 0.5691(14) 0.8172(11) 0.5517(9) 0.033(3) Uani 1 1 d . . . . .
C31 C 0.9677(14) 1.2108(12) 0.6492(9) 0.040(3) Uani 1 1 d . . . . .
H31 H 0.9397 1.2932 0.6482 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6359(12) 0.7061(11) 0.5194(8) 0.029(3) Uani 1 1 d . . . . .
C15 C 0.4681(14) 0.2901(13) 0.8525(9) 0.043(3) Uani 1 1 d . . . . .
H15 H 0.4419 0.2074 0.8539 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6492(13) 0.4456(13) 0.8089(10) 0.041(3) Uani 1 1 d . . . . .
H13 H 0.7414 0.4712 0.7820 0.049 Uiso 1 1 calc R U . . .
C30 C 1.1063(16) 1.1741(15) 0.6856(10) 0.055(4) Uani 1 1 d . . . . .
H30 H 1.1717 1.2321 0.7072 0.066 Uiso 1 1 calc R U . . .
C2 C 0.0739(14) 0.8394(13) 1.0652(10) 0.045(3) Uani 1 1 d . . . . .
H2 H -0.0053 0.7989 1.0998 0.054 Uiso 1 1 calc R U . . .
C22 C 0.5770(14) 0.6593(13) 0.4347(9) 0.045(3) Uani 1 1 d . . . . .
H22 H 0.4980 0.6991 0.3994 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6086(15) 0.3294(15) 0.8148(9) 0.051(4) Uani 1 1 d . . . . .
H14 H 0.6747 0.2716 0.7934 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3028(15) 0.9658(12) 0.9602(11) 0.046(4) Uani 1 1 d . . . . .
H5 H 0.3810 1.0071 0.9250 0.055 Uiso 1 1 calc R U . . .
C21 C 0.6374(17) 0.5530(14) 0.4036(11) 0.054(4) Uani 1 1 d . . . . .
H21 H 0.6014 0.5236 0.3452 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2477(17) 1.0109(14) 1.0420(12) 0.059(4) Uani 1 1 d . . . . .
H4 H 0.2846 1.0841 1.0621 0.070 Uiso 1 1 calc R U . . .
C20 C 0.7480(17) 0.4906(13) 0.4563(11) 0.052(4) Uani 1 1 d . . . . .
H20 H 0.7865 0.4186 0.4346 0.062 Uiso 1 1 calc R U . . .
C3 C 0.1349(17) 0.9474(15) 1.0968(11) 0.061(4) Uani 1 1 d . . . . .
H3 H 0.0991 0.9768 1.1555 0.073 Uiso 1 1 calc R U . . .
C19 C 0.8007(16) 0.5325(13) 0.5386(12) 0.053(4) Uani 1 1 d . . . . .
H19 H 0.8755 0.4883 0.5750 0.064 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 C12 1.877(11) . ?
Br2 C28 1.866(11) . ?
O1 C7 1.170(13) . ?
O2 C23 1.181(13) . ?
C26 C24 1.325(14) . ?
C26 C27 1.436(14) . ?
C26 H26 0.9300 . ?
C11 C12 1.373(14) . ?
C11 C16 1.381(16) . ?
C11 C10 1.445(14) . ?
C24 C25 1.424(17) . ?
C24 C23 1.483(15) . ?
C27 C32 1.364(15) . ?
C27 C28 1.402(15) . ?
N2 C25 1.134(15) . ?
C10 C8 1.318(14) . ?
C10 H10 0.9300 . ?
C28 C29 1.354(16) . ?
C1 C6 1.378(16) . ?
C1 C2 1.389(16) . ?
C1 C7 1.478(16) . ?
C6 C5 1.372(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.488(15) . ?
C8 C9 1.399(17) . ?
C12 C13 1.366(16) . ?
N1 C9 1.144(16) . ?
C16 C15 1.351(16) . ?
C16 H16 0.9300 . ?
C29 C30 1.366(19) . ?
C29 H29 0.9300 . ?
C32 C31 1.346(17) . ?
C32 H32 0.9300 . ?
C18 C17 1.380(16) . ?
C18 C19 1.391(17) . ?
C18 H18 0.9300 . ?
C23 C17 1.455(16) . ?
C31 C30 1.376(19) . ?
C31 H31 0.9300 . ?
C17 C22 1.390(16) . ?
C15 C14 1.404(19) . ?
C15 H15 0.9300 . ?
C13 C14 1.312(19) . ?
C13 H13 0.9300 . ?
C30 H30 0.9300 . ?
C2 C3 1.40(2) . ?
C2 H2 0.9300 . ?
C22 C21 1.380(18) . ?
C22 H22 0.9300 . ?
C14 H14 0.9300 . ?
C5 C4 1.33(2) . ?
C5 H5 0.9300 . ?
C21 C20 1.35(2) . ?
C21 H21 0.9300 . ?
C4 C3 1.39(2) . ?
C4 H4 0.9300 . ?
C20 C19 1.32(2) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?

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
C24 C26 C27 128.0(9) . . ?
C24 C26 H26 116.0 . . ?
C27 C26 H26 116.0 . . ?
C12 C11 C16 120.0(10) . . ?
C12 C11 C10 121.0(10) . . ?
C16 C11 C10 119.0(10) . . ?
C26 C24 C25 120.5(10) . . ?
C26 C24 C23 125.2(9) . . ?
C25 C24 C23 114.3(9) . . ?
C32 C27 C28 118.4(10) . . ?
C32 C27 C26 121.6(10) . . ?
C28 C27 C26 120.0(10) . . ?
C8 C10 C11 128.5(10) . . ?
C8 C10 H10 115.8 . . ?
C11 C10 H10 115.8 . . ?
C29 C28 C27 121.9(11) . . ?
C29 C28 Br2 118.7(9) . . ?
C27 C28 Br2 119.5(8) . . ?
C6 C1 C2 120.4(11) . . ?
C6 C1 C7 123.1(10) . . ?
C2 C1 C7 116.3(11) . . ?
C5 C6 C1 119.7(11) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N2 C25 C24 177.3(15) . . ?
O1 C7 C1 123.0(11) . . ?
O1 C7 C8 119.2(11) . . ?
C1 C7 C8 117.5(10) . . ?
C10 C8 C9 120.6(10) . . ?
C10 C8 C7 125.4(10) . . ?
C9 C8 C7 114.0(9) . . ?
C13 C12 C11 122.2(11) . . ?
C13 C12 Br1 118.6(9) . . ?
C11 C12 Br1 119.1(8) . . ?
C15 C16 C11 117.2(12) . . ?
C15 C16 H16 121.4 . . ?
C11 C16 H16 121.4 . . ?
C28 C29 C30 118.2(11) . . ?
C28 C29 H29 120.9 . . ?
C30 C29 H29 120.9 . . ?
N1 C9 C8 174.7(15) . . ?
C31 C32 C27 119.9(12) . . ?
C31 C32 H32 120.1 . . ?
C27 C32 H32 120.0 . . ?
C17 C18 C19 119.2(12) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
O2 C23 C17 122.9(11) . . ?
O2 C23 C24 118.4(10) . . ?
C17 C23 C24 118.4(10) . . ?
C32 C31 C30 121.2(13) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C18 C17 C22 118.6(12) . . ?
C18 C17 C23 123.0(10) . . ?
C22 C17 C23 118.2(11) . . ?
C16 C15 C14 121.1(13) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C14 C13 C12 117.8(12) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C29 C30 C31 120.4(12) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C1 C2 C3 117.5(13) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C21 C22 C17 119.1(13) . . ?
C21 C22 H22 120.5 . . ?
C17 C22 H22 120.5 . . ?
C13 C14 C15 121.7(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C4 C5 C6 121.8(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C20 C21 C22 121.4(13) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C5 C4 C3 119.4(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C19 C20 C21 119.6(13) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C4 C3 C2 121.0(12) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C20 C19 C18 121.9(14) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?

_refine_diff_density_max         1.069
_refine_diff_density_min         -2.412
_refine_diff_density_rms         0.339

