# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1436250'
_audit_update_record             
;
2015-11-11 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Br2 N O2'
_chemical_formula_weight         421.09

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7580(18)
_cell_length_b                   9.0190(18)
_cell_length_c                   10.089(2)
_cell_angle_alpha                93.78(3)
_cell_angle_beta                 98.83(3)
_cell_angle_gamma                107.13(3)
_cell_volume                     747.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    5.429
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.4098
_exptl_absorpt_correction_T_max  0.6128
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2927
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.1283
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2738
_reflns_number_gt                1445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2738
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1576
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.4079(9) 0.1576(9) 0.3291(7) 0.0348(19) Uani 1 1 d . . .
Br1 Br 0.97404(13) 0.74526(12) 0.38823(10) 0.0486(4) Uani 1 1 d . . .
O1 O 0.4698(9) 0.1762(9) 0.8844(6) 0.061(2) Uani 1 1 d . . .
C1 C 0.5328(10) 0.2992(9) 0.3260(8) 0.024 Uani 1 1 d . . .
Br2 Br 0.71933(15) 0.42815(15) 0.79312(12) 0.0680(5) Uani 1 1 d . . .
O2 O 0.3062(7) 0.0128(8) 0.4909(6) 0.0461(18) Uani 1 1 d . . .
C2 C 0.5752(10) 0.3645(11) 0.2160(8) 0.034(2) Uani 1 1 d . . .
H2A H 0.5196 0.3191 0.1299 0.040 Uiso 1 1 calc R . .
C3 C 0.7070(11) 0.5042(11) 0.2349(9) 0.041(3) Uani 1 1 d . . .
H3A H 0.7363 0.5547 0.1609 0.049 Uiso 1 1 calc R . .
C4 C 0.7900(11) 0.5641(10) 0.3606(10) 0.034(2) Uani 1 1 d . . .
C5 C 0.7441(10) 0.4934(11) 0.4728(8) 0.034(2) Uani 1 1 d . . .
H5A H 0.8023 0.5361 0.5587 0.041 Uiso 1 1 calc R . .
C6 C 0.6128(9) 0.3606(10) 0.4568(8) 0.026(2) Uani 1 1 d . . .
C7 C 0.5340(9) 0.2599(10) 0.5512(8) 0.029(2) Uani 1 1 d . . .
C8 C 0.4007(11) 0.1239(11) 0.4576(9) 0.038(2) Uani 1 1 d . . .
C9 C 0.5557(10) 0.2718(10) 0.6859(8) 0.029(2) Uani 1 1 d . . .
C10 C 0.4445(12) 0.1658(12) 0.7654(11) 0.044(3) Uani 1 1 d . . .
H10A H 0.3524 0.0893 0.7182 0.053 Uiso 1 1 calc R . .
C11 C 0.2877(11) 0.0645(11) 0.2096(8) 0.038(3) Uani 1 1 d . . .
H11A H 0.3426 0.0592 0.1338 0.046 Uiso 1 1 calc R . .
H11B H 0.2410 -0.0412 0.2301 0.046 Uiso 1 1 calc R . .
C12 C 0.1559(10) 0.1343(10) 0.1718(9) 0.034(2) Uani 1 1 d . . .
C13 C 0.0515(11) 0.1443(11) 0.2502(9) 0.038(2) Uani 1 1 d . . .
H13A H 0.0648 0.1107 0.3351 0.046 Uiso 1 1 calc R . .
C14 C -0.0754(11) 0.2013(12) 0.2140(9) 0.041(3) Uani 1 1 d . . .
H14A H -0.1480 0.2037 0.2719 0.050 Uiso 1 1 calc R . .
C15 C -0.0933(12) 0.2564(12) 0.0867(10) 0.042(3) Uani 1 1 d . . .
H15A H -0.1749 0.3008 0.0607 0.050 Uiso 1 1 calc R . .
C16 C 0.0092(12) 0.2438(11) 0.0037(9) 0.038(2) Uani 1 1 d . . .
H16A H -0.0046 0.2760 -0.0818 0.046 Uiso 1 1 calc R . .
C17 C 0.1303(12) 0.1860(11) 0.0418(9) 0.039(2) Uani 1 1 d . . .
H17A H 0.1999 0.1791 -0.0177 0.047 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
N C8 1.358(11) . ?
N C1 1.422(10) . ?
N C11 1.491(10) . ?
Br1 C4 1.896(8) . ?
O1 C10 1.180(11) . ?
C1 C2 1.341(11) . ?
C1 C6 1.390(11) . ?
Br2 C9 1.828(9) . ?
O2 C8 1.202(10) . ?
C2 C3 1.414(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.351(12) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(11) . ?
C5 C6 1.374(11) . ?
C5 H5A 0.9300 . ?
C6 C7 1.467(11) . ?
C7 C9 1.336(11) . ?
C7 C8 1.557(11) . ?
C9 C10 1.516(13) . ?
C10 H10A 0.9300 . ?
C11 C12 1.483(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.316(12) . ?
C12 C17 1.428(12) . ?
C13 C14 1.367(12) . ?
C13 H13A 0.9300 . ?
C14 C15 1.411(13) . ?
C14 H14A 0.9300 . ?
C15 C16 1.341(13) . ?
C15 H15A 0.9300 . ?
C16 C17 1.331(13) . ?
C16 H16A 0.9300 . ?
C17 H17A 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
C8 N C1 111.4(7) . . ?
C8 N C11 123.1(7) . . ?
C1 N C11 125.2(7) . . ?
C2 C1 C6 123.4(8) . . ?
C2 C1 N 126.9(7) . . ?
C6 C1 N 109.6(7) . . ?
C1 C2 C3 118.0(8) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 119.8(9) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.9(8) . . ?
C3 C4 Br1 120.8(7) . . ?
C5 C4 Br1 118.3(7) . . ?
C6 C5 C4 120.1(7) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C1 117.6(8) . . ?
C5 C6 C7 133.7(7) . . ?
C1 C6 C7 108.6(7) . . ?
C9 C7 C6 132.7(8) . . ?
C9 C7 C8 123.4(8) . . ?
C6 C7 C8 103.9(7) . . ?
O2 C8 N 126.0(8) . . ?
O2 C8 C7 127.6(8) . . ?
N C8 C7 106.4(7) . . ?
C7 C9 C10 124.5(8) . . ?
C7 C9 Br2 122.3(6) . . ?
C10 C9 Br2 113.1(6) . . ?
O1 C10 C9 122.9(9) . . ?
O1 C10 H10A 118.6 . . ?
C9 C10 H10A 118.6 . . ?
C12 C11 N 111.5(8) . . ?
C12 C11 H11A 109.3 . . ?
N C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C17 116.3(9) . . ?
C13 C12 C11 123.1(9) . . ?
C17 C12 C11 120.5(9) . . ?
C12 C13 C14 123.8(9) . . ?
C12 C13 H13A 118.1 . . ?
C14 C13 H13A 118.1 . . ?
C13 C14 C15 118.2(8) . . ?
C13 C14 H14A 120.9 . . ?
C15 C14 H14A 120.9 . . ?
C16 C15 C14 119.0(9) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C17 C16 C15 121.1(9) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C16 C17 C12 121.6(9) . . ?
C16 C17 H17A 119.2 . . ?
C12 C17 H17A 119.2 . . ?

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
C8 N C1 C2 178.4(9) . . . . ?
C11 N C1 C2 -7.5(15) . . . . ?
C8 N C1 C6 0.8(11) . . . . ?
C11 N C1 C6 175.0(8) . . . . ?
C6 C1 C2 C3 -0.9(14) . . . . ?
N C1 C2 C3 -178.1(9) . . . . ?
C1 C2 C3 C4 2.8(14) . . . . ?
C2 C3 C4 C5 -2.4(15) . . . . ?
C2 C3 C4 Br1 176.7(7) . . . . ?
C3 C4 C5 C6 0.1(14) . . . . ?
Br1 C4 C5 C6 -179.0(7) . . . . ?
C4 C5 C6 C1 1.7(13) . . . . ?
C4 C5 C6 C7 -179.8(9) . . . . ?
C2 C1 C6 C5 -1.3(14) . . . . ?
N C1 C6 C5 176.3(8) . . . . ?
C2 C1 C6 C7 179.9(9) . . . . ?
N C1 C6 C7 -2.5(10) . . . . ?
C5 C6 C7 C9 6.8(18) . . . . ?
C1 C6 C7 C9 -174.7(10) . . . . ?
C5 C6 C7 C8 -175.6(10) . . . . ?
C1 C6 C7 C8 3.0(9) . . . . ?
C1 N C8 O2 179.1(10) . . . . ?
C11 N C8 O2 4.9(16) . . . . ?
C1 N C8 C7 1.1(10) . . . . ?
C11 N C8 C7 -173.2(8) . . . . ?
C9 C7 C8 O2 -2.5(16) . . . . ?
C6 C7 C8 O2 179.5(10) . . . . ?
C9 C7 C8 N 175.5(9) . . . . ?
C6 C7 C8 N -2.5(10) . . . . ?
C6 C7 C9 C10 170.7(9) . . . . ?
C8 C7 C9 C10 -6.6(15) . . . . ?
C6 C7 C9 Br2 -5.6(15) . . . . ?
C8 C7 C9 Br2 177.1(7) . . . . ?
C7 C9 C10 O1 177.5(10) . . . . ?
Br2 C9 C10 O1 -5.9(13) . . . . ?
C8 N C11 C12 95.1(11) . . . . ?
C1 N C11 C12 -78.4(11) . . . . ?
N C11 C12 C13 -64.9(11) . . . . ?
N C11 C12 C17 119.1(8) . . . . ?
C17 C12 C13 C14 -0.5(14) . . . . ?
C11 C12 C13 C14 -176.7(8) . . . . ?
C12 C13 C14 C15 -1.7(15) . . . . ?
C13 C14 C15 C16 3.3(14) . . . . ?
C14 C15 C16 C17 -2.6(15) . . . . ?
C15 C16 C17 C12 0.3(14) . . . . ?
C13 C12 C17 C16 1.3(13) . . . . ?
C11 C12 C17 C16 177.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.977
_refine_diff_density_rms         0.143
