# 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_g150806a
_database_code_depnum_ccdc_archive 'CCDC 1425225'
_audit_update_record             
;
2015-09-16 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 Br N O'
_chemical_formula_sum            'C9 H8 Br N O'
_chemical_formula_weight         226.07

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.9498(4)
_cell_length_b                   8.2018(3)
_cell_length_c                   16.5817(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.327(3)
_cell_angle_gamma                90.00
_cell_volume                     1746.79(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    3215
_cell_measurement_theta_min      2.9520
_cell_measurement_theta_max      27.7390

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    4.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2927
_exptl_absorpt_correction_T_max  0.4563
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9227
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3239
_reflns_number_gt                2525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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)+(0.0352P)²+1.1240P] 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         3239
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Br1 Br 0.32304(3) 0.45365(5) 0.15798(2) 0.04536(14) Uani 1 1 d . . .
Br2 Br 0.23145(3) 0.94609(5) 0.18893(2) 0.05252(15) Uani 1 1 d . . .
O1 O 0.1024(2) 0.4579(3) 0.23548(14) 0.0526(7) Uani 1 1 d . . .
O2 O 0.4762(2) 0.8573(4) 0.25011(14) 0.0523(7) Uani 1 1 d . . .
N1 N 0.0443(2) 0.3237(3) 0.11703(15) 0.0306(6) Uani 1 1 d . . .
N2 N 0.4846(2) 0.7943(3) 0.11643(16) 0.0345(7) Uani 1 1 d . . .
C1 C 0.1062(3) 0.4299(4) 0.16405(19) 0.0340(8) Uani 1 1 d . . .
C2 C 0.1810(3) 0.5048(4) 0.1102(2) 0.0334(8) Uani 1 1 d . . .
H2 H 0.1710 0.6243 0.1063 0.040 Uiso 1 1 calc R . .
C3 C 0.1502(2) 0.4267(4) 0.02938(18) 0.0287(7) Uani 1 1 d . . .
C4 C 0.1867(3) 0.4451(5) -0.0449(2) 0.0428(9) Uani 1 1 d . . .
H4 H 0.2422 0.5163 -0.0507 0.051 Uiso 1 1 calc R . .
C5 C 0.1393(3) 0.3558(5) -0.1112(2) 0.0485(10) Uani 1 1 d . . .
H5 H 0.1628 0.3668 -0.1622 0.058 Uiso 1 1 calc R . .
C6 C 0.0585(3) 0.2518(5) -0.1020(2) 0.0447(10) Uani 1 1 d . . .
H6 H 0.0279 0.1923 -0.1473 0.054 Uiso 1 1 calc R . .
C7 C 0.0208(3) 0.2318(4) -0.02830(19) 0.0350(8) Uani 1 1 d . . .
H7 H -0.0348 0.1607 -0.0227 0.042 Uiso 1 1 calc R . .
C8 C 0.0685(2) 0.3210(4) 0.03684(17) 0.0285(7) Uani 1 1 d . . .
C9 C -0.0355(3) 0.2249(5) 0.1480(2) 0.0505(10) Uani 1 1 d . . .
H9A H -0.0430 0.2586 0.2030 0.076 Uiso 1 1 calc R . .
H9B H -0.0154 0.1110 0.1480 0.076 Uiso 1 1 calc R . .
H9C H -0.1012 0.2394 0.1135 0.076 Uiso 1 1 calc R . .
C10 C 0.4457(3) 0.8721(4) 0.1781(2) 0.0369(8) Uani 1 1 d . . .
C11 C 0.3582(3) 0.9840(4) 0.1398(2) 0.0371(8) Uani 1 1 d . . .
H11 H 0.3798 1.0992 0.1480 0.044 Uiso 1 1 calc R . .
C12 C 0.3490(3) 0.9434(4) 0.0512(2) 0.0331(8) Uani 1 1 d . . .
C13 C 0.2830(3) 0.9992(5) -0.0143(2) 0.0440(9) Uani 1 1 d . . .
H13 H 0.2298 1.0739 -0.0072 0.053 Uiso 1 1 calc R . .
C14 C 0.2963(3) 0.9429(5) -0.0912(2) 0.0519(11) Uani 1 1 d . . .
H14 H 0.2517 0.9795 -0.1367 0.062 Uiso 1 1 calc R . .
C15 C 0.3740(3) 0.8343(5) -0.1013(2) 0.0522(11) Uani 1 1 d . . .
H15 H 0.3817 0.7978 -0.1539 0.063 Uiso 1 1 calc R . .
C16 C 0.4418(3) 0.7769(5) -0.0356(2) 0.0439(9) Uani 1 1 d . . .
H16 H 0.4951 0.7024 -0.0428 0.053 Uiso 1 1 calc R . .
C17 C 0.4277(3) 0.8337(4) 0.04031(19) 0.0319(8) Uani 1 1 d . . .
C18 C 0.5724(3) 0.6827(5) 0.1284(3) 0.0534(11) Uani 1 1 d . . .
H18A H 0.6050 0.6892 0.1843 0.080 Uiso 1 1 calc R . .
H18B H 0.6226 0.7121 0.0921 0.080 Uiso 1 1 calc R . .
H18C H 0.5481 0.5723 0.1166 0.080 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 C2 1.953(3) . ?
Br2 C11 1.949(3) . ?
O1 C1 1.214(4) . ?
O2 C10 1.214(4) . ?
N1 C1 1.361(4) . ?
N1 C8 1.405(4) . ?
N1 C9 1.456(4) . ?
N2 C10 1.356(4) . ?
N2 C17 1.416(4) . ?
N2 C18 1.453(4) . ?
C1 C2 1.528(5) . ?
C2 C3 1.492(4) . ?
C2 H2 0.9900 . ?
C3 C4 1.383(5) . ?
C3 C8 1.386(4) . ?
C4 C5 1.396(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9400 . ?
C6 C7 1.382(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.384(4) . ?
C7 H7 0.9400 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.532(5) . ?
C11 C12 1.495(5) . ?
C11 H11 0.9900 . ?
C12 C13 1.373(5) . ?
C12 C17 1.388(5) . ?
C13 C14 1.387(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.370(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
C1 N1 C8 111.5(3) . . ?
C1 N1 C9 123.2(3) . . ?
C8 N1 C9 125.3(3) . . ?
C10 N2 C17 111.3(3) . . ?
C10 N2 C18 123.6(3) . . ?
C17 N2 C18 125.1(3) . . ?
O1 C1 N1 125.9(3) . . ?
O1 C1 C2 127.1(3) . . ?
N1 C1 C2 107.1(3) . . ?
C3 C2 C1 103.6(3) . . ?
C3 C2 Br1 113.7(2) . . ?
C1 C2 Br1 108.1(2) . . ?
C3 C2 H2 110.4 . . ?
C1 C2 H2 110.4 . . ?
Br1 C2 H2 110.4 . . ?
C4 C3 C8 120.0(3) . . ?
C4 C3 C2 132.1(3) . . ?
C8 C3 C2 107.9(3) . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 117.0(3) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C7 C8 C3 122.1(3) . . ?
C7 C8 N1 128.0(3) . . ?
C3 C8 N1 109.9(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N2 126.1(3) . . ?
O2 C10 C11 126.8(3) . . ?
N2 C10 C11 107.1(3) . . ?
C12 C11 C10 103.7(3) . . ?
C12 C11 Br2 114.2(2) . . ?
C10 C11 Br2 110.4(2) . . ?
C12 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
Br2 C11 H11 109.5 . . ?
C13 C12 C17 120.4(3) . . ?
C13 C12 C11 131.8(3) . . ?
C17 C12 C11 107.7(3) . . ?
C12 C13 C14 118.6(4) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.6(4) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 117.2(4) . . ?
C17 C16 H16 121.4 . . ?
C15 C16 H16 121.4 . . ?
C16 C17 C12 121.6(3) . . ?
C16 C17 N2 128.6(3) . . ?
C12 C17 N2 109.8(3) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 N1 C1 O1 179.5(3) . . . . ?
C9 N1 C1 O1 -1.3(5) . . . . ?
C8 N1 C1 C2 -0.9(4) . . . . ?
C9 N1 C1 C2 178.3(3) . . . . ?
O1 C1 C2 C3 -179.9(3) . . . . ?
N1 C1 C2 C3 0.6(3) . . . . ?
O1 C1 C2 Br1 59.1(4) . . . . ?
N1 C1 C2 Br1 -120.4(2) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
Br1 C2 C3 C4 -64.2(4) . . . . ?
C1 C2 C3 C8 -0.1(3) . . . . ?
Br1 C2 C3 C8 117.1(3) . . . . ?
C8 C3 C4 C5 0.1(5) . . . . ?
C2 C3 C4 C5 -178.5(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C3 0.2(5) . . . . ?
C6 C7 C8 N1 179.3(3) . . . . ?
C4 C3 C8 C7 -0.1(5) . . . . ?
C2 C3 C8 C7 178.8(3) . . . . ?
C4 C3 C8 N1 -179.4(3) . . . . ?
C2 C3 C8 N1 -0.5(4) . . . . ?
C1 N1 C8 C7 -178.3(3) . . . . ?
C9 N1 C8 C7 2.5(5) . . . . ?
C1 N1 C8 C3 0.9(4) . . . . ?
C9 N1 C8 C3 -178.3(3) . . . . ?
C17 N2 C10 O2 177.1(3) . . . . ?
C18 N2 C10 O2 -1.8(5) . . . . ?
C17 N2 C10 C11 -4.0(4) . . . . ?
C18 N2 C10 C11 177.1(3) . . . . ?
O2 C10 C11 C12 -175.8(3) . . . . ?
N2 C10 C11 C12 5.3(4) . . . . ?
O2 C10 C11 Br2 -53.1(4) . . . . ?
N2 C10 C11 Br2 128.0(2) . . . . ?
C10 C11 C12 C13 178.0(4) . . . . ?
Br2 C11 C12 C13 57.8(5) . . . . ?
C10 C11 C12 C17 -4.7(4) . . . . ?
Br2 C11 C12 C17 -124.9(3) . . . . ?
C17 C12 C13 C14 0.3(5) . . . . ?
C11 C12 C13 C14 177.2(4) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
C15 C16 C17 N2 179.5(3) . . . . ?
C13 C12 C17 C16 -0.3(5) . . . . ?
C11 C12 C17 C16 -177.9(3) . . . . ?
C13 C12 C17 N2 -179.8(3) . . . . ?
C11 C12 C17 N2 2.6(4) . . . . ?
C10 N2 C17 C16 -178.5(3) . . . . ?
C18 N2 C17 C16 0.4(5) . . . . ?
C10 N2 C17 C12 1.0(4) . . . . ?
C18 N2 C17 C12 179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
