# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nas105

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br N O4'
_chemical_formula_sum            'C12 H12 Br N O4'
_chemical_formula_weight         314.14

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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   6.2850(4)
_cell_length_b                   19.1650(13)
_cell_length_c                   10.0101(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1205.74(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8704
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    3.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4704
_exptl_absorpt_correction_T_max  0.5784
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Smart 1000 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            21721
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         30.09
_reflns_number_total             3515
_reflns_number_gt                3214
_reflns_threshold_expression     I>2u(I)

_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

_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)+(0.0219P)²+0.9917P] 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   0.003(8)
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 -0.16144(3) 0.317302(10) 0.82560(3) 0.01784(6) Uani 1 1 d . . .
O1 O 0.3849(3) 0.32941(9) 0.24184(18) 0.0161(3) Uani 1 1 d . . .
O2 O 0.6418(3) 0.29926(10) 0.10297(18) 0.0198(3) Uani 1 1 d . . .
O3 O 0.6509(3) 0.46740(12) 0.0746(3) 0.0420(6) Uani 1 1 d . . .
O4 O 0.4428(4) 0.53692(11) 0.1816(2) 0.0354(5) Uani 1 1 d . . .
N1 N 0.4749(3) 0.48496(11) 0.1138(2) 0.0214(4) Uani 1 1 d . . .
C1 C 0.4761(4) 0.32980(11) 0.1194(2) 0.0154(4) Uani 1 1 d . . .
C2 C 0.3604(4) 0.37196(12) 0.0146(2) 0.0167(4) Uani 1 1 d . . .
H2A H 0.2390 0.3445 -0.0203 0.020 Uiso 1 1 calc R . .
H2B H 0.4579 0.3818 -0.0607 0.020 Uiso 1 1 calc R . .
C3 C 0.2788(4) 0.44063(12) 0.0723(2) 0.0161(4) Uani 1 1 d . . .
C4 C 0.1471(4) 0.42842(12) 0.1991(2) 0.0181(4) Uani 1 1 d . . .
H4A H 0.1980 0.4600 0.2705 0.022 Uiso 1 1 calc R . .
H4B H -0.0038 0.4398 0.1809 0.022 Uiso 1 1 calc R . .
C5 C 0.1629(3) 0.35301(13) 0.2473(3) 0.0139(5) Uani 1 1 d . . .
H5A H 0.0743 0.3226 0.1881 0.017 Uiso 1 1 calc R . .
C6 C 0.1645(4) 0.48443(14) -0.0326(2) 0.0195(5) Uani 1 1 d . . .
H6A H 0.0366 0.4598 -0.0628 0.029 Uiso 1 1 calc R . .
H6B H 0.2595 0.4922 -0.1088 0.029 Uiso 1 1 calc R . .
H6C H 0.1240 0.5294 0.0063 0.029 Uiso 1 1 calc R . .
C7 C 0.0892(4) 0.34478(12) 0.3894(2) 0.0153(5) Uani 1 1 d . . .
C8 C 0.2158(4) 0.36385(12) 0.4974(2) 0.0162(4) Uani 1 1 d . . .
H8A H 0.3540 0.3822 0.4816 0.019 Uiso 1 1 calc R . .
C9 C 0.1440(4) 0.35655(12) 0.6276(2) 0.0173(4) Uani 1 1 d . . .
H9A H 0.2320 0.3690 0.7009 0.021 Uiso 1 1 calc R . .
C10 C -0.0605(4) 0.33042(12) 0.6484(2) 0.0162(4) Uani 1 1 d . . .
C11 C -0.1924(4) 0.31328(12) 0.5434(2) 0.0157(4) Uani 1 1 d . . .
H11A H -0.3331 0.2973 0.5598 0.019 Uiso 1 1 calc R . .
C12 C -0.1170(4) 0.31959(11) 0.4126(2) 0.0155(4) Uani 1 1 d . . .
H12A H -0.2054 0.3069 0.3396 0.019 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 C10 1.900(2) . ?
O1 C1 1.353(3) . ?
O1 C5 1.468(3) . ?
O2 C1 1.206(3) . ?
O3 N1 1.221(3) . ?
O4 N1 1.222(3) . ?
N1 C3 1.554(3) . ?
C1 C2 1.510(3) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C6 1.524(3) . ?
C3 C4 1.534(3) . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.505(3) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.391(3) . ?
C7 C12 1.403(3) . ?
C8 C9 1.386(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.395(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(3) . ?
C11 C12 1.398(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?

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 O1 C5 115.74(19) . . ?
O3 N1 O4 123.6(2) . . ?
O3 N1 C3 118.8(2) . . ?
O4 N1 C3 117.6(2) . . ?
O2 C1 O1 119.1(2) . . ?
O2 C1 C2 125.5(2) . . ?
O1 C1 C2 115.35(19) . . ?
C1 C2 C3 111.15(19) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C6 C3 C2 111.9(2) . . ?
C6 C3 C4 113.59(19) . . ?
C2 C3 C4 111.27(19) . . ?
C6 C3 N1 104.89(19) . . ?
C2 C3 N1 107.83(19) . . ?
C4 C3 N1 106.85(19) . . ?
C5 C4 C3 111.76(19) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O1 C5 C7 107.2(2) . . ?
O1 C5 C4 109.99(18) . . ?
C7 C5 C4 112.2(2) . . ?
O1 C5 H5A 109.1 . . ?
C7 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.4(2) . . ?
C8 C7 C5 122.1(2) . . ?
C12 C7 C5 118.5(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9A 120.8 . . ?
C10 C9 H9A 120.8 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 Br1 118.65(18) . . ?
C9 C10 Br1 119.64(18) . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12A 120.1 . . ?
C7 C12 H12A 120.1 . . ?

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
C5 O1 C1 O2 -166.2(2) . . . . ?
C5 O1 C1 C2 16.0(3) . . . . ?
O2 C1 C2 C3 -136.5(2) . . . . ?
O1 C1 C2 C3 41.2(3) . . . . ?
C1 C2 C3 C6 179.1(2) . . . . ?
C1 C2 C3 C4 -52.6(3) . . . . ?
C1 C2 C3 N1 64.2(2) . . . . ?
O3 N1 C3 C6 -106.0(3) . . . . ?
O4 N1 C3 C6 72.1(3) . . . . ?
O3 N1 C3 C2 13.4(3) . . . . ?
O4 N1 C3 C2 -168.5(2) . . . . ?
O3 N1 C3 C4 133.1(2) . . . . ?
O4 N1 C3 C4 -48.8(3) . . . . ?
C6 C3 C4 C5 136.9(2) . . . . ?
C2 C3 C4 C5 9.5(3) . . . . ?
N1 C3 C4 C5 -108.0(2) . . . . ?
C1 O1 C5 C7 176.91(19) . . . . ?
C1 O1 C5 C4 -60.9(3) . . . . ?
C3 C4 C5 O1 44.4(3) . . . . ?
C3 C4 C5 C7 163.62(19) . . . . ?
O1 C5 C7 C8 43.1(3) . . . . ?
C4 C5 C7 C8 -77.7(3) . . . . ?
O1 C5 C7 C12 -139.43(19) . . . . ?
C4 C5 C7 C12 99.7(2) . . . . ?
C12 C7 C8 C9 1.9(3) . . . . ?
C5 C7 C8 C9 179.3(2) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C8 C9 C10 Br1 178.29(18) . . . . ?
C9 C10 C11 C12 2.5(3) . . . . ?
Br1 C10 C11 C12 -177.08(17) . . . . ?
C10 C11 C12 C7 -1.5(3) . . . . ?
C8 C7 C12 C11 -0.6(3) . . . . ?
C5 C7 C12 C11 -178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.09
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.087

_database_code_depnum_ccdc_archive 'CCDC 959160'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nas135

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br N O4'
_chemical_formula_sum            'C12 H12 Br N O4'
_chemical_formula_weight         314.14

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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   12.3354(6)
_cell_length_b                   14.4555(7)
_cell_length_c                   6.7455(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1202.82(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5709
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.45

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    3.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3640
_exptl_absorpt_correction_T_max  0.9013
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15622
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.52
_reflns_number_total             3668
_reflns_number_gt                3244
_reflns_threshold_expression     I>2u(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'

_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)+(0.0121P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(7)
_refine_ls_number_reflns         3668
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 1.087710(12) 0.504944(9) 0.06907(6) 0.01530(4) Uani 1 1 d . . .
O1 O 1.11281(9) 0.15820(8) 0.39773(18) 0.0123(2) Uani 1 1 d . . .
O2 O 1.28585(10) 0.19659(8) 0.38578(19) 0.0168(3) Uani 1 1 d . . .
O3 O 1.22847(10) 0.26590(9) -0.0771(2) 0.0202(3) Uani 1 1 d . . .
O4 O 1.08011(11) 0.29637(10) -0.2359(2) 0.0220(3) Uani 1 1 d . . .
N1 N 1.13309(12) 0.28933(9) -0.0829(2) 0.0130(3) Uani 1 1 d . . .
C1 C 1.19267(15) 0.21914(11) 0.3582(3) 0.0127(3) Uani 1 1 d . . .
C2 C 1.15615(14) 0.31264(12) 0.2808(3) 0.0116(3) Uani 1 1 d . . .
H2A H 1.2202 0.3471 0.2320 0.014 Uiso 1 1 calc R . .
H2B H 1.1242 0.3485 0.3913 0.014 Uiso 1 1 calc R . .
C3 C 1.07306(13) 0.30521(11) 0.1136(2) 0.0099(3) Uani 1 1 d . . .
C4 C 0.99761(14) 0.22025(13) 0.1414(3) 0.0125(3) Uani 1 1 d . . .
H4A H 0.9224 0.2370 0.1050 0.015 Uiso 1 1 calc R . .
H4B H 1.0215 0.1692 0.0538 0.015 Uiso 1 1 calc R . .
C5 C 1.00148(13) 0.18899(11) 0.3563(2) 0.0119(3) Uani 1 1 d . . .
H5A H 0.9834 0.2425 0.4443 0.014 Uiso 1 1 calc R . .
C6 C 1.00299(13) 0.39135(10) 0.0904(3) 0.0128(3) Uani 1 1 d . . .
H6A H 0.9539 0.3963 0.2060 0.015 Uiso 1 1 calc R . .
H6B H 0.9575 0.3846 -0.0297 0.015 Uiso 1 1 calc R . .
C7 C 0.92849(13) 0.10887(11) 0.4059(3) 0.0118(3) Uani 1 1 d . . .
C8 C 0.87300(13) 0.11036(11) 0.5871(3) 0.0153(3) Uani 1 1 d . . .
H8A H 0.8819 0.1614 0.6744 0.018 Uiso 1 1 calc R . .
C9 C 0.80532(16) 0.03802(13) 0.6399(3) 0.0180(4) Uani 1 1 d . . .
H9A H 0.7690 0.0388 0.7640 0.022 Uiso 1 1 calc R . .
C10 C 0.79079(15) -0.03605(13) 0.5098(3) 0.0175(4) Uani 1 1 d . . .
H10A H 0.7434 -0.0852 0.5447 0.021 Uiso 1 1 calc R . .
C11 C 0.84492(15) -0.03818(12) 0.3306(3) 0.0171(4) Uani 1 1 d . . .
H11A H 0.8349 -0.0889 0.2430 0.021 Uiso 1 1 calc R . .
C12 C 0.91453(14) 0.03418(13) 0.2780(3) 0.0145(3) Uani 1 1 d . . .
H12A H 0.9522 0.0324 0.1552 0.017 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 C6 1.9518(16) . ?
O1 C1 1.348(2) . ?
O1 C5 1.4704(19) . ?
O2 C1 1.209(2) . ?
O3 N1 1.2249(19) . ?
O4 N1 1.2260(19) . ?
N1 C3 1.535(2) . ?
C1 C2 1.517(2) . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C6 1.524(2) . ?
C3 C4 1.552(2) . ?
C4 C5 1.519(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.505(2) . ?
C5 H5A 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.393(2) . ?
C7 C8 1.401(2) . ?
C8 C9 1.385(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.396(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?

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 O1 C5 116.56(13) . . ?
O3 N1 O4 124.17(16) . . ?
O3 N1 C3 118.52(15) . . ?
O4 N1 C3 117.20(14) . . ?
O2 C1 O1 119.22(15) . . ?
O2 C1 C2 125.11(16) . . ?
O1 C1 C2 115.66(15) . . ?
C1 C2 C3 112.99(14) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C6 C3 C2 113.50(14) . . ?
C6 C3 N1 107.90(13) . . ?
C2 C3 N1 108.91(13) . . ?
C6 C3 C4 108.59(13) . . ?
C2 C3 C4 111.62(13) . . ?
N1 C3 C4 105.98(12) . . ?
C5 C4 C3 109.39(13) . . ?
C5 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C5 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
O1 C5 C7 106.47(13) . . ?
O1 C5 C4 107.51(13) . . ?
C7 C5 C4 115.00(14) . . ?
O1 C5 H5A 109.2 . . ?
C7 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C3 C6 Br1 113.04(11) . . ?
C3 C6 H6A 109.0 . . ?
Br1 C6 H6A 109.0 . . ?
C3 C6 H6B 109.0 . . ?
Br1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 119.47(15) . . ?
C12 C7 C5 122.18(15) . . ?
C8 C7 C5 118.35(15) . . ?
C9 C8 C7 120.49(17) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 119.67(17) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 120.34(17) . . ?
C11 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C10 C11 C12 120.14(17) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C7 C12 C11 119.88(17) . . ?
C7 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?

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
C5 O1 C1 O2 -178.48(14) . . . . ?
C5 O1 C1 C2 1.5(2) . . . . ?
O2 C1 C2 C3 132.38(18) . . . . ?
O1 C1 C2 C3 -47.6(2) . . . . ?
C1 C2 C3 C6 156.77(14) . . . . ?
C1 C2 C3 N1 -83.02(17) . . . . ?
C1 C2 C3 C4 33.66(19) . . . . ?
O3 N1 C3 C6 138.61(14) . . . . ?
O4 N1 C3 C6 -45.14(18) . . . . ?
O3 N1 C3 C2 15.00(19) . . . . ?
O4 N1 C3 C2 -168.75(14) . . . . ?
O3 N1 C3 C4 -105.22(16) . . . . ?
O4 N1 C3 C4 71.03(17) . . . . ?
C6 C3 C4 C5 -106.43(16) . . . . ?
C2 C3 C4 C5 19.43(19) . . . . ?
N1 C3 C4 C5 137.87(14) . . . . ?
C1 O1 C5 C7 178.31(13) . . . . ?
C1 O1 C5 C4 54.57(17) . . . . ?
C3 C4 C5 O1 -63.79(17) . . . . ?
C3 C4 C5 C7 177.84(13) . . . . ?
C2 C3 C6 Br1 51.97(18) . . . . ?
N1 C3 C6 Br1 -68.82(15) . . . . ?
C4 C3 C6 Br1 176.73(11) . . . . ?
O1 C5 C7 C12 -79.19(18) . . . . ?
C4 C5 C7 C12 39.8(2) . . . . ?
O1 C5 C7 C8 100.96(16) . . . . ?
C4 C5 C7 C8 -140.09(16) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C5 C7 C8 C9 -179.68(16) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C5 C7 C12 C11 -179.43(16) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.52
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.062

_database_code_depnum_ccdc_archive 'CCDC 959161'
