# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1444178'
_audit_update_record             
;
2015-12-24 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Br N3 O3'
_chemical_formula_weight         372.18

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.029(3)
_cell_length_b                   9.545(3)
_cell_length_c                   17.249(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.859(4)
_cell_angle_gamma                90.00
_cell_volume                     1468.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3529
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.97

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.818
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5512
_exptl_absorpt_correction_T_max  0.6310
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8414
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.40
_reflns_number_total             3258
_reflns_number_gt                2606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0402P)²+0.4465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3258
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19484(3) 1.10091(3) 1.088992(16) 0.05850(12) Uani 1 1 d . . .
C10 C 0.5445(2) 0.6041(2) 0.87775(12) 0.0351(4) Uani 1 1 d . . .
O3 O 0.45932(18) 0.66084(18) 0.82558(8) 0.0464(4) Uani 1 1 d . . .
C6 C 0.4572(2) 0.7367(2) 0.98495(11) 0.0324(4) Uani 1 1 d . . .
N1 N 0.2184(2) 0.6872(2) 0.89555(11) 0.0445(4) Uani 1 1 d . . .
C5 C 0.5255(2) 0.8091(2) 1.05463(11) 0.0328(4) Uani 1 1 d . . .
O1 O 0.2312(2) 0.55982(18) 0.90036(11) 0.0553(4) Uani 1 1 d . . .
C4 C 0.4496(2) 0.9191(2) 1.08699(11) 0.0341(4) Uani 1 1 d . . .
N2 N 0.6628(2) 0.7613(2) 1.08807(10) 0.0430(4) Uani 1 1 d . . .
C2 C 0.2377(2) 0.8860(2) 0.98378(13) 0.0393(5) Uani 1 1 d . . .
H2 H 0.1426 0.9118 0.9593 0.047 Uiso 1 1 calc R . .
O2 O 0.1254(2) 0.7483(2) 0.84803(11) 0.0712(6) Uani 1 1 d . . .
N3 N 0.54361(19) 0.63382(18) 0.95601(10) 0.0358(4) Uani 1 1 d . . .
H3 H 0.6014 0.5846 0.9898 0.043 Uiso 1 1 calc R . .
C12 C 0.6079(3) 0.4004(2) 0.80167(13) 0.0444(5) Uani 1 1 d . . .
H12 H 0.5129 0.4089 0.7723 0.053 Uiso 1 1 calc R . .
C3 C 0.3044(2) 0.9570(2) 1.04791(12) 0.0375(4) Uani 1 1 d . . .
C1 C 0.3125(2) 0.7734(2) 0.95446(12) 0.0356(4) Uani 1 1 d . . .
C7 C 0.5227(3) 0.9818(2) 1.15675(12) 0.0432(5) Uani 1 1 d . . .
H7 H 0.4781 1.0556 1.1797 0.052 Uiso 1 1 calc R . .
C11 C 0.6544(2) 0.4948(2) 0.86202(11) 0.0368(4) Uani 1 1 d . . .
C13 C 0.7022(3) 0.2941(3) 0.78511(14) 0.0518(6) Uani 1 1 d . . .
H13 H 0.6690 0.2291 0.7461 0.062 Uiso 1 1 calc R . .
C9 C 0.7239(3) 0.8216(3) 1.15436(14) 0.0529(6) Uani 1 1 d . . .
H9 H 0.8160 0.7879 1.1789 0.063 Uiso 1 1 calc R . .
C15 C 0.8937(3) 0.3785(3) 0.88538(18) 0.0616(7) Uani 1 1 d . . .
H15 H 0.9905 0.3717 0.9128 0.074 Uiso 1 1 calc R . .
C14 C 0.8446(3) 0.2842(3) 0.82610(16) 0.0578(7) Uani 1 1 d . . .
H14 H 0.9083 0.2137 0.8140 0.069 Uiso 1 1 calc R . .
C8 C 0.6594(3) 0.9324(3) 1.18991(13) 0.0517(6) Uani 1 1 d . . .
H8 H 0.7093 0.9722 1.2358 0.062 Uiso 1 1 calc R . .
C16 C 0.7981(2) 0.4835(3) 0.90390(14) 0.0497(6) Uani 1 1 d . . .
H16 H 0.8305 0.5461 0.9443 0.060 Uiso 1 1 calc R . .


_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 C3 1.893(2) . ?
C10 O3 1.217(2) . ?
C10 N3 1.380(3) . ?
C10 C11 1.494(3) . ?
C6 C1 1.376(3) . ?
C6 N3 1.394(3) . ?
C6 C5 1.440(3) . ?
N1 O1 1.223(3) . ?
N1 O2 1.227(2) . ?
N1 C1 1.472(3) . ?
C5 N2 1.362(3) . ?
C5 C4 1.415(3) . ?
C4 C7 1.413(3) . ?
C4 C3 1.425(3) . ?
N2 C9 1.323(3) . ?
C2 C3 1.357(3) . ?
C2 C1 1.404(3) . ?
C2 H2 0.9300 . ?
N3 H3 0.8600 . ?
C12 C13 1.382(3) . ?
C12 C11 1.392(3) . ?
C12 H12 0.9300 . ?
C7 C8 1.362(3) . ?
C7 H7 0.9300 . ?
C11 C16 1.389(3) . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C9 C8 1.394(4) . ?
C9 H9 0.9300 . ?
C15 C14 1.383(4) . ?
C15 C16 1.392(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16 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
O3 C10 N3 122.3(2) . . ?
O3 C10 C11 122.57(19) . . ?
N3 C10 C11 115.15(17) . . ?
C1 C6 N3 126.37(18) . . ?
C1 C6 C5 117.15(18) . . ?
N3 C6 C5 116.47(17) . . ?
O1 N1 O2 124.5(2) . . ?
O1 N1 C1 118.06(18) . . ?
O2 N1 C1 117.3(2) . . ?
N2 C5 C4 123.08(18) . . ?
N2 C5 C6 115.95(18) . . ?
C4 C5 C6 120.92(18) . . ?
C7 C4 C5 117.31(19) . . ?
C7 C4 C3 124.8(2) . . ?
C5 C4 C3 117.90(18) . . ?
C9 N2 C5 116.9(2) . . ?
C3 C2 C1 119.88(19) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C10 N3 C6 125.63(17) . . ?
C10 N3 H3 117.2 . . ?
C6 N3 H3 117.2 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C2 C3 C4 121.30(19) . . ?
C2 C3 Br1 118.40(16) . . ?
C4 C3 Br1 120.18(15) . . ?
C6 C1 C2 122.54(19) . . ?
C6 C1 N1 122.35(18) . . ?
C2 C1 N1 114.69(18) . . ?
C8 C7 C4 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
C4 C7 H7 120.5 . . ?
C16 C11 C12 119.3(2) . . ?
C16 C11 C10 123.6(2) . . ?
C12 C11 C10 117.10(19) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N2 C9 C8 124.3(2) . . ?
N2 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C11 C16 C15 120.0(2) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

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
C1 C6 C5 N2 173.65(18) . . . . ?
N3 C6 C5 N2 -4.9(3) . . . . ?
C1 C6 C5 C4 -3.9(3) . . . . ?
N3 C6 C5 C4 177.51(17) . . . . ?
N2 C5 C4 C7 0.8(3) . . . . ?
C6 C5 C4 C7 178.13(18) . . . . ?
N2 C5 C4 C3 -178.10(19) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C4 C5 N2 C9 0.9(3) . . . . ?
C6 C5 N2 C9 -176.6(2) . . . . ?
O3 C10 N3 C6 -5.3(3) . . . . ?
C11 C10 N3 C6 176.24(18) . . . . ?
C1 C6 N3 C10 37.5(3) . . . . ?
C5 C6 N3 C10 -144.0(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 Br1 -176.38(16) . . . . ?
C7 C4 C3 C2 -175.8(2) . . . . ?
C5 C4 C3 C2 3.0(3) . . . . ?
C7 C4 C3 Br1 0.0(3) . . . . ?
C5 C4 C3 Br1 178.83(14) . . . . ?
N3 C6 C1 C2 -174.93(19) . . . . ?
C5 C6 C1 C2 6.6(3) . . . . ?
N3 C6 C1 N1 12.9(3) . . . . ?
C5 C6 C1 N1 -165.51(18) . . . . ?
C3 C2 C1 C6 -4.6(3) . . . . ?
C3 C2 C1 N1 168.09(19) . . . . ?
O1 N1 C1 C6 35.8(3) . . . . ?
O2 N1 C1 C6 -148.8(2) . . . . ?
O1 N1 C1 C2 -136.9(2) . . . . ?
O2 N1 C1 C2 38.4(3) . . . . ?
C5 C4 C7 C8 -1.2(3) . . . . ?
C3 C4 C7 C8 177.6(2) . . . . ?
C13 C12 C11 C16 1.9(3) . . . . ?
C13 C12 C11 C10 -178.3(2) . . . . ?
O3 C10 C11 C16 142.2(2) . . . . ?
N3 C10 C11 C16 -39.4(3) . . . . ?
O3 C10 C11 C12 -37.7(3) . . . . ?
N3 C10 C11 C12 140.8(2) . . . . ?
C11 C12 C13 C14 -2.5(4) . . . . ?
C5 N2 C9 C8 -2.2(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C16 C15 C14 C13 0.4(4) . . . . ?
C4 C7 C8 C9 0.0(4) . . . . ?
N2 C9 C8 C7 1.8(4) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
C10 C11 C16 C15 -180.0(2) . . . . ?
C14 C15 C16 C11 -1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.081
