# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1470798'
_audit_update_record             
;
2016-03-27 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O'
_chemical_formula_sum            'C12 H9 Br N2 O'
_chemical_formula_weight         277.12

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/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   4.5103(3)
_cell_length_b                   19.8005(15)
_cell_length_c                   12.1942(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.592(7)
_cell_angle_gamma                90.00
_cell_volume                     1083.84(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4449
_cell_measurement_theta_min      1.9642
_cell_measurement_theta_max      25.2014

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    3.770
_exptl_absorpt_correction_T_min  0.67600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '130 images, ΔΦ 2.0°'
_diffrn_detector_area_resol_mean 6.66
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10312
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.26
_reflns_number_total             1934
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON
_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)+(0.0591P)²+0.5952P] 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         1934
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_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 1.12976(8) 0.581116(18) 0.04772(3) 0.05761(18) Uani 1 1 d . . .
C2 C 0.9917(6) 0.64001(15) 0.1545(2) 0.0380(7) Uani 1 1 d . . .
C3 C 1.0970(7) 0.63224(17) 0.2638(3) 0.0436(7) Uani 1 1 d . . .
H3 H 1.2352 0.5986 0.2848 0.052 Uiso 1 1 calc R . .
C4 C 0.9970(7) 0.67421(18) 0.3409(2) 0.0467(8) Uani 1 1 d . . .
H4 H 1.0694 0.6692 0.4145 0.056 Uiso 1 1 calc R . .
C5 C 0.7893(6) 0.72419(16) 0.3114(2) 0.0387(7) Uani 1 1 d . . .
C6 C 0.6778(6) 0.73133(15) 0.2007(2) 0.0340(6) Uani 1 1 d . . .
C7 C 0.7834(6) 0.68827(15) 0.1226(2) 0.0373(7) Uani 1 1 d . . .
H7 H 0.7122 0.6924 0.0487 0.045 Uiso 1 1 calc R . .
O8 O 0.6991(6) 0.76494(14) 0.39042(17) 0.0586(7) Uani 1 1 d . . .
H8 H 0.5794 0.7926 0.3624 0.088 Uiso 1 1 calc R . .
C9 C 0.4554(6) 0.78187(16) 0.1652(2) 0.0371(7) Uani 1 1 d . . .
H9 H 0.3820 0.7834 0.0913 0.045 Uiso 1 1 calc R . .
N10 N 0.3575(5) 0.82401(13) 0.23123(19) 0.0375(6) Uani 1 1 d . . .
C11 C 0.1430(6) 0.87372(15) 0.1938(2) 0.0358(6) Uani 1 1 d . . .
C12 C 0.0603(8) 0.91991(17) 0.2699(3) 0.0484(8) Uani 1 1 d . . .
H12 H 0.1416 0.9178 0.3429 0.058 Uiso 1 1 calc R . .
C13 C -0.1449(8) 0.96932(19) 0.2362(3) 0.0552(9) Uani 1 1 d . . .
H13 H -0.2041 1.0009 0.2862 0.066 Uiso 1 1 calc R . .
C14 C -0.2601(7) 0.97116(18) 0.1276(3) 0.0515(8) Uani 1 1 d . . .
H14 H -0.3958 1.0050 0.1053 0.062 Uiso 1 1 calc R . .
N15 N -0.1865(7) 0.92690(15) 0.0534(2) 0.0542(8) Uani 1 1 d . . .
C16 C 0.0118(7) 0.87955(19) 0.0869(3) 0.0501(8) Uani 1 1 d . . .
H16 H 0.0653 0.8485 0.0352 0.060 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0706(3) 0.0482(3) 0.0524(3) -0.01235(15) -0.00231(18) 0.01096(16)
C2 0.0404(15) 0.0342(16) 0.0387(15) -0.0007(12) 0.0003(12) -0.0037(13)
C3 0.0412(16) 0.0430(18) 0.0449(17) 0.0076(14) -0.0049(14) 0.0041(14)
C4 0.0464(17) 0.061(2) 0.0301(14) 0.0081(14) -0.0078(13) 0.0086(15)
C5 0.0392(15) 0.0469(19) 0.0295(14) -0.0007(12) -0.0003(12) -0.0008(13)
C6 0.0323(14) 0.0382(16) 0.0303(14) 0.0021(11) -0.0034(11) -0.0027(11)
C7 0.0407(15) 0.0401(17) 0.0294(13) 0.0011(12) -0.0053(12) -0.0060(13)
O8 0.0665(15) 0.0769(19) 0.0303(11) -0.0037(11) -0.0067(10) 0.0259(13)
C9 0.0361(14) 0.0459(18) 0.0282(14) 0.0023(12) -0.0038(11) -0.0030(13)
N10 0.0315(12) 0.0455(15) 0.0339(12) -0.0004(11) -0.0052(10) 0.0001(10)
C11 0.0310(14) 0.0415(17) 0.0334(15) -0.0008(12) -0.0043(11) -0.0042(12)
C12 0.0480(18) 0.056(2) 0.0387(17) -0.0070(14) -0.0074(14) 0.0048(15)
C13 0.054(2) 0.055(2) 0.055(2) -0.0143(17) -0.0017(16) 0.0116(17)
C14 0.0462(18) 0.046(2) 0.059(2) -0.0006(16) -0.0110(16) 0.0071(15)
N15 0.0541(17) 0.060(2) 0.0452(16) -0.0055(13) -0.0133(13) 0.0161(14)
C16 0.0503(18) 0.059(2) 0.0387(17) -0.0091(15) -0.0076(14) 0.0112(16)

_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 1.898(3) . ?
C2 C7 1.369(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 O8 1.350(4) . ?
C5 C6 1.402(4) . ?
C6 C7 1.396(4) . ?
C6 C9 1.453(4) . ?
C7 H7 0.9300 . ?
O8 H8 0.8200 . ?
C9 N10 1.268(4) . ?
C9 H9 0.9300 . ?
N10 C11 1.424(4) . ?
C11 C12 1.380(4) . ?
C11 C16 1.383(4) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 N15 1.325(4) . ?
C14 H14 0.9300 . ?
N15 C16 1.332(4) . ?
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
C7 C2 C3 121.0(3) . . ?
C7 C2 Br1 119.7(2) . . ?
C3 C2 Br1 119.3(2) . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
O8 C5 C4 119.0(3) . . ?
O8 C5 C6 121.5(3) . . ?
C4 C5 C6 119.5(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C9 119.3(2) . . ?
C5 C6 C9 121.9(3) . . ?
C2 C7 C6 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C5 O8 H8 109.5 . . ?
N10 C9 C6 122.5(3) . . ?
N10 C9 H9 118.8 . . ?
C6 C9 H9 118.8 . . ?
C9 N10 C11 121.3(2) . . ?
C12 C11 C16 117.4(3) . . ?
C12 C11 N10 117.6(3) . . ?
C16 C11 N10 125.1(3) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N15 C14 C13 123.0(3) . . ?
N15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 N15 C16 117.5(3) . . ?
N15 C16 C11 124.1(3) . . ?
N15 C16 H16 117.9 . . ?
C11 C16 H16 117.9 . . ?

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
C7 C2 C3 C4 -1.4(5) . . . . ?
Br1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 O8 -179.4(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
O8 C5 C6 C7 179.0(3) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
O8 C5 C6 C9 -1.3(5) . . . . ?
C4 C5 C6 C9 178.7(3) . . . . ?
C3 C2 C7 C6 1.1(4) . . . . ?
Br1 C2 C7 C6 179.3(2) . . . . ?
C5 C6 C7 C2 0.1(4) . . . . ?
C9 C6 C7 C2 -179.6(3) . . . . ?
C7 C6 C9 N10 -177.6(3) . . . . ?
C5 C6 C9 N10 2.7(5) . . . . ?
C6 C9 N10 C11 179.0(3) . . . . ?
C9 N10 C11 C12 -176.6(3) . . . . ?
C9 N10 C11 C16 3.1(5) . . . . ?
C16 C11 C12 C13 -0.4(5) . . . . ?
N10 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 N15 1.0(6) . . . . ?
C13 C14 N15 C16 -1.0(6) . . . . ?
C14 N15 C16 C11 0.4(6) . . . . ?
C12 C11 C16 N15 0.4(5) . . . . ?
N10 C11 C16 N15 -179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1470799'
_audit_update_record             
;
2016-03-27 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Br N2 O'
_chemical_formula_sum            'C12 H9 Br N2 O'
_chemical_formula_weight         277.12

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           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   6.1946(6)
_cell_length_b                   7.0152(7)
_cell_length_c                   25.100(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1090.77(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3926
_cell_measurement_theta_min      2.8978
_cell_measurement_theta_max      25.6690

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    3.746
_exptl_absorpt_correction_T_min  0.31966
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 2.0°'
_diffrn_detector_area_resol_mean 6.66
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9101
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.72
_reflns_number_total             2076
_reflns_number_gt                1838
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON
_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)+(0.0462P)²+3.5879P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         2076
_refine_ls_number_parameters     145
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 1.07243(6) 0.70948(5) 0.76892(2) 0.04648(9) Uani 1 1 d . . .
C2 C 0.8868(6) 0.7254(5) 0.70876(17) 0.0315(9) Uani 1 1 d U . .
C3 C 0.6782(7) 0.7885(5) 0.71574(17) 0.0372(10) Uani 1 1 d U . .
H3 H 0.6260 0.8141 0.7497 0.045 Uiso 1 1 calc R . .
C4 C 0.5466(6) 0.8135(6) 0.67152(17) 0.0383(11) Uani 1 1 d . . .
H4 H 0.4039 0.8511 0.6762 0.046 Uiso 1 1 calc R . .
C5 C 0.6247(6) 0.7835(6) 0.62091(17) 0.0359(10) Uani 1 1 d . . .
C6 C 0.8398(6) 0.7220(5) 0.61327(16) 0.0317(9) Uani 1 1 d . . .
C7 C 0.9649(7) 0.6917(5) 0.65888(16) 0.0354(10) Uani 1 1 d U . .
H7 H 1.1055 0.6473 0.6551 0.042 Uiso 1 1 calc R . .
O8 O 0.4943(5) 0.8141(5) 0.57826(12) 0.0475(9) Uani 1 1 d . . .
H8 H 0.5629 0.7974 0.5507 0.071 Uiso 1 1 calc R . .
C9 C 0.9319(7) 0.7030(5) 0.56115(16) 0.0360(10) Uani 1 1 d . . .
H9 H 1.0757 0.6664 0.5583 0.043 Uiso 1 1 calc R . .
N10 N 0.8248(5) 0.7341(4) 0.51835(15) 0.0334(8) Uani 1 1 d . . .
C11 C 0.9284(7) 0.7337(5) 0.46806(16) 0.0347(10) Uani 1 1 d . . .
C12 C 0.8151(7) 0.6697(6) 0.42426(16) 0.0386(11) Uani 1 1 d . . .
H12 H 0.6763 0.6209 0.4279 0.046 Uiso 1 1 calc R . .
C13 C 0.9108(7) 0.6796(6) 0.37550(18) 0.0445(12) Uani 1 1 d . . .
H13 H 0.8338 0.6309 0.3468 0.053 Uiso 1 1 calc R . .
N14 N 1.1054(7) 0.7528(6) 0.36525(15) 0.0476(11) Uani 1 1 d . . .
C15 C 1.2095(8) 0.8179(6) 0.40883(18) 0.0448(12) Uani 1 1 d . . .
H15 H 1.3462 0.8698 0.4039 0.054 Uiso 1 1 calc R . .
C16 C 1.1301(7) 0.8139(6) 0.45993(17) 0.0363(10) Uani 1 1 d . . .
H16 H 1.2093 0.8634 0.4882 0.044 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04661(18) 0.05938(19) 0.03343(15) 0.0042(3) -0.0019(2) 0.00437(19)
C2 0.0182(16) 0.0284(17) 0.048(2) 0.0031(17) 0.0028(15) -0.0016(14)
C3 0.041(2) 0.0251(17) 0.045(2) 0.0024(17) 0.0109(17) -0.0013(16)
C4 0.024(2) 0.040(2) 0.052(2) 0.0000(18) 0.0071(17) 0.0022(16)
C5 0.0261(19) 0.038(2) 0.044(2) 0.0048(18) -0.0031(16) -0.0028(17)
C6 0.0289(18) 0.0211(16) 0.045(2) -0.0043(16) 0.0030(16) -0.0002(16)
C7 0.039(2) 0.0341(19) 0.0332(18) 0.0014(16) 0.0027(16) -0.0023(17)
O8 0.0302(13) 0.0645(19) 0.0479(17) -0.0013(15) -0.0065(13) 0.0025(14)
C9 0.0311(19) 0.0334(18) 0.043(2) -0.0021(17) -0.0050(17) -0.0056(17)
N10 0.0255(15) 0.0305(14) 0.0441(16) -0.0024(15) 0.0012(16) -0.0023(12)
C11 0.042(2) 0.0270(17) 0.035(2) -0.0036(15) 0.0005(17) 0.0027(18)
C12 0.032(2) 0.041(2) 0.043(2) -0.0040(18) -0.0020(17) -0.0027(18)
C13 0.048(2) 0.042(2) 0.043(2) -0.0041(18) -0.0094(19) 0.007(2)
N14 0.050(2) 0.057(2) 0.0357(19) 0.0014(16) 0.0059(17) 0.0051(19)
C15 0.040(2) 0.038(2) 0.057(3) 0.002(2) 0.007(2) -0.0039(18)
C16 0.034(2) 0.034(2) 0.041(2) -0.0036(17) -0.0012(18) -0.0033(17)

_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 1.901(4) . ?
C2 C7 1.363(6) . ?
C2 C3 1.377(6) . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(6) . ?
C4 H4 0.9300 . ?
C5 O8 1.358(5) . ?
C5 C6 1.413(6) . ?
C6 C7 1.399(6) . ?
C6 C9 1.433(6) . ?
C7 H7 0.9300 . ?
O8 H8 0.8200 . ?
C9 N10 1.281(5) . ?
C9 H9 0.9300 . ?
N10 C11 1.416(5) . ?
C11 C12 1.379(6) . ?
C11 C16 1.386(6) . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C13 N14 1.335(6) . ?
C13 H13 0.9300 . ?
N14 C15 1.350(6) . ?
C15 C16 1.374(6) . ?
C15 H15 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
C7 C2 C3 120.4(4) . . ?
C7 C2 Br1 120.3(3) . . ?
C3 C2 Br1 119.0(3) . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
O8 C5 C4 119.6(4) . . ?
O8 C5 C6 120.1(4) . . ?
C4 C5 C6 120.2(4) . . ?
C7 C6 C5 117.2(4) . . ?
C7 C6 C9 120.8(4) . . ?
C5 C6 C9 121.8(4) . . ?
C2 C7 C6 121.9(4) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C5 O8 H8 109.5 . . ?
N10 C9 C6 122.9(4) . . ?
N10 C9 H9 118.5 . . ?
C6 C9 H9 118.5 . . ?
C9 N10 C11 120.8(3) . . ?
C12 C11 C16 118.3(4) . . ?
C12 C11 N10 118.7(4) . . ?
C16 C11 N10 122.6(4) . . ?
C13 C12 C11 118.6(4) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
N14 C13 C12 125.9(4) . . ?
N14 C13 H13 117.1 . . ?
C12 C13 H13 117.1 . . ?
C13 N14 C15 113.9(4) . . ?
N14 C15 C16 125.3(4) . . ?
N14 C15 H15 117.3 . . ?
C16 C15 H15 117.3 . . ?
C15 C16 C11 118.0(4) . . ?
C15 C16 H16 121.0 . . ?
C11 C16 H16 121.0 . . ?

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
C7 C2 C3 C4 1.4(6) . . . . ?
Br1 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 -2.6(6) . . . . ?
C3 C4 C5 O8 -178.2(4) . . . . ?
C3 C4 C5 C6 1.5(6) . . . . ?
O8 C5 C6 C7 -179.5(3) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
O8 C5 C6 C9 4.4(6) . . . . ?
C4 C5 C6 C9 -175.2(4) . . . . ?
C3 C2 C7 C6 1.0(6) . . . . ?
Br1 C2 C7 C6 -173.0(3) . . . . ?
C5 C6 C7 C2 -2.0(5) . . . . ?
C9 C6 C7 C2 174.0(4) . . . . ?
C7 C6 C9 N10 -178.2(4) . . . . ?
C5 C6 C9 N10 -2.3(6) . . . . ?
C6 C9 N10 C11 173.1(3) . . . . ?
C9 N10 C11 C12 146.8(4) . . . . ?
C9 N10 C11 C16 -40.4(5) . . . . ?
C16 C11 C12 C13 3.2(6) . . . . ?
N10 C11 C12 C13 176.3(4) . . . . ?
C11 C12 C13 N14 -2.5(7) . . . . ?
C12 C13 N14 C15 1.0(7) . . . . ?
C13 N14 C15 C16 -0.3(6) . . . . ?
N14 C15 C16 C11 1.2(7) . . . . ?
C12 C11 C16 C15 -2.6(6) . . . . ?
N10 C11 C16 C15 -175.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.72
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.098
