# 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_Entry6(A)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N2 O3'
_chemical_formula_weight         266.25

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/c

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                   5.9087(14)
_cell_length_b                   7.3564(17)
_cell_length_c                   27.796(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.569(5)
_cell_angle_gamma                90.00
_cell_volume                     1205.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    682
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      24.14

_exptl_crystal_description       PLATES
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9896
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6319
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2367
_reflns_number_gt                1501
_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    ORTEP
_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)+(0.0466P)²+0.7115P] 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         2367
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
O1 O 0.3228(4) 0.6339(3) 0.36717(7) 0.0238(5) Uani 1 1 d . . .
O2 O 0.6719(4) 0.8505(3) 0.61549(8) 0.0403(7) Uani 1 1 d . . .
O3 O 0.9419(4) 0.9376(3) 0.57143(8) 0.0329(6) Uani 1 1 d . . .
N1 N 0.0392(4) 0.5355(4) 0.41005(9) 0.0254(7) Uani 1 1 d . . .
N2 N 0.7550(5) 0.8683(4) 0.57636(9) 0.0261(7) Uani 1 1 d . . .
C1 C 0.4057(6) 0.6264(5) 0.26768(12) 0.0262(8) Uani 1 1 d . . .
C2 C 0.4375(6) 0.6269(5) 0.21887(12) 0.0279(8) Uani 1 1 d . . .
C3 C 0.2721(6) 0.5592(5) 0.18637(13) 0.0305(9) Uani 1 1 d . . .
C4 C 0.0731(6) 0.4892(5) 0.20279(12) 0.0290(8) Uani 1 1 d . . .
C5 C 0.0414(6) 0.4859(5) 0.25100(13) 0.0276(8) Uani 1 1 d . . .
C6 C 0.2038(5) 0.5559(4) 0.28431(11) 0.0224(8) Uani 1 1 d . . .
C7 C 0.1600(5) 0.5562(4) 0.33531(11) 0.0225(7) Uani 1 1 d . . .
C8 C -0.0071(6) 0.4986(5) 0.36179(13) 0.0284(9) Uani 1 1 d . . .
C9 C 0.2338(5) 0.6165(4) 0.41119(11) 0.0222(8) Uani 1 1 d . . .
C10 C 0.3700(5) 0.6854(4) 0.45304(11) 0.0214(7) Uani 1 1 d . . .
C11 C 0.2846(5) 0.6680(4) 0.49863(11) 0.0227(8) Uani 1 1 d . . .
H11 H 0.1427 0.6163 0.5017 0.027 Uiso 1 1 calc R . .
C12 C 0.4111(6) 0.7276(4) 0.53905(11) 0.0206(7) Uani 1 1 d . . .
C13 C 0.6206(5) 0.8039(4) 0.53330(11) 0.0200(7) Uani 1 1 d . . .
C14 C 0.7096(5) 0.8238(4) 0.48880(10) 0.0206(7) Uani 1 1 d . . .
H14 H 0.8514 0.8761 0.4860 0.025 Uiso 1 1 calc R . .
C15 C 0.5818(5) 0.7637(4) 0.44869(11) 0.0219(8) Uani 1 1 d . . .
H15 H 0.6382 0.7758 0.4184 0.026 Uiso 1 1 calc R . .
H1 H 0.511(5) 0.676(4) 0.2899(10) 0.011(8) Uiso 1 1 d . . .
H2 H 0.562(6) 0.666(4) 0.2075(11) 0.025(9) Uiso 1 1 d . . .
H3 H 0.285(5) 0.562(4) 0.1533(11) 0.019(8) Uiso 1 1 d . . .
H4 H -0.029(5) 0.444(4) 0.1810(11) 0.016(8) Uiso 1 1 d . . .
H5 H -0.072(5) 0.444(4) 0.2620(10) 0.010(8) Uiso 1 1 d . . .
H8 H -0.110(5) 0.439(4) 0.3538(10) 0.004(8) Uiso 1 1 d . . .
H12 H 0.365(5) 0.717(4) 0.5705(11) 0.024(9) Uiso 1 1 d . . .

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
O1 0.0235(13) 0.0264(12) 0.0215(12) 0.0002(9) 0.0012(10) -0.0018(10)
O2 0.0368(16) 0.0634(18) 0.0214(14) -0.0055(12) 0.0076(12) -0.0033(13)
O3 0.0231(14) 0.0414(15) 0.0338(15) 0.0016(11) -0.0010(11) -0.0105(12)
N1 0.0185(16) 0.0282(16) 0.0292(17) -0.0022(12) 0.0006(12) -0.0062(13)
N2 0.0286(18) 0.0259(15) 0.0235(16) -0.0013(12) -0.0013(13) 0.0044(14)
C1 0.025(2) 0.0278(19) 0.026(2) -0.0010(15) -0.0001(16) -0.0019(16)
C2 0.023(2) 0.028(2) 0.033(2) 0.0032(15) 0.0063(17) -0.0007(17)
C3 0.043(2) 0.0271(19) 0.021(2) -0.0006(15) 0.0038(17) 0.0027(17)
C4 0.028(2) 0.031(2) 0.027(2) -0.0017(15) -0.0057(16) -0.0069(17)
C5 0.020(2) 0.027(2) 0.036(2) 0.0019(15) 0.0036(16) -0.0043(16)
C6 0.0236(19) 0.0187(17) 0.0246(18) 0.0006(13) -0.0010(14) 0.0028(14)
C7 0.0223(19) 0.0190(17) 0.0257(18) -0.0002(13) -0.0030(14) -0.0003(14)
C8 0.021(2) 0.033(2) 0.031(2) -0.0038(16) -0.0009(16) -0.0105(18)
C9 0.025(2) 0.0200(18) 0.0219(18) 0.0012(13) 0.0055(15) 0.0039(15)
C10 0.0211(19) 0.0175(17) 0.0254(18) -0.0001(13) 0.0004(15) 0.0047(14)
C11 0.0198(18) 0.0197(17) 0.0292(19) 0.0043(14) 0.0063(15) 0.0026(14)
C12 0.025(2) 0.0193(17) 0.0181(18) 0.0009(13) 0.0060(15) 0.0037(14)
C13 0.0205(19) 0.0177(17) 0.0217(18) 0.0004(13) 0.0005(14) 0.0041(14)
C14 0.0185(18) 0.0207(17) 0.0230(18) 0.0015(13) 0.0040(14) 0.0007(14)
C15 0.0218(19) 0.0221(18) 0.0224(18) 0.0046(13) 0.0057(15) 0.0015(14)

_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
O1 C9 1.368(3) . ?
O1 C7 1.389(4) . ?
O2 N2 1.228(3) . ?
O3 N2 1.232(3) . ?
N1 C9 1.293(4) . ?
N1 C8 1.379(4) . ?
N2 C13 1.473(4) . ?
C1 C2 1.381(5) . ?
C1 C6 1.405(4) . ?
C1 H1 0.92(3) . ?
C2 C3 1.382(5) . ?
C2 H2 0.87(3) . ?
C3 C4 1.387(5) . ?
C3 H3 0.93(3) . ?
C4 C5 1.365(5) . ?
C4 H4 0.89(3) . ?
C5 C6 1.390(5) . ?
C5 H5 0.81(3) . ?
C6 C7 1.457(4) . ?
C7 C8 1.337(4) . ?
C8 H8 0.77(3) . ?
C9 C10 1.464(4) . ?
C10 C15 1.390(4) . ?
C10 C11 1.399(4) . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(4) . ?
C12 H12 0.93(3) . ?
C13 C14 1.382(4) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 H15 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
C9 O1 C7 104.0(2) . . ?
C9 N1 C8 103.7(3) . . ?
O2 N2 O3 123.6(3) . . ?
O2 N2 C13 117.4(3) . . ?
O3 N2 C13 119.0(3) . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 H1 121.9(17) . . ?
C6 C1 H1 118.4(17) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 122(2) . . ?
C3 C2 H2 118(2) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 122.8(19) . . ?
C4 C3 H3 117.3(19) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 122.0(19) . . ?
C3 C4 H4 117.9(19) . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 123(2) . . ?
C6 C5 H5 116(2) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 119.4(3) . . ?
C1 C6 C7 121.7(3) . . ?
C8 C7 O1 106.6(3) . . ?
C8 C7 C6 135.8(3) . . ?
O1 C7 C6 117.6(3) . . ?
C7 C8 N1 111.4(3) . . ?
C7 C8 H8 128(2) . . ?
N1 C8 H8 120(2) . . ?
N1 C9 O1 114.3(3) . . ?
N1 C9 C10 128.6(3) . . ?
O1 C9 C10 117.1(3) . . ?
C15 C10 C11 119.6(3) . . ?
C15 C10 C9 121.9(3) . . ?
C11 C10 C9 118.5(3) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 117.1(19) . . ?
C11 C12 H12 124.2(19) . . ?
C12 C13 C14 122.8(3) . . ?
C12 C13 N2 118.7(3) . . ?
C14 C13 N2 118.5(3) . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 964937'
#######################################################################
#
#                 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_Entry18

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 Br Cl F3 N O'
_chemical_formula_weight         402.59

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   7.538(4)
_cell_length_b                   8.691(5)
_cell_length_c                   11.877(7)
_cell_angle_alpha                80.826(9)
_cell_angle_beta                 83.217(9)
_cell_angle_gamma                73.581(8)
_cell_volume                     734.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4685
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.14

_exptl_crystal_description       PLATES
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    3.015
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4649
_exptl_absorpt_correction_T_max  0.7137
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5850
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3098
_reflns_number_gt                2873
_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    ORTEP
_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)+(0.0955P)²+0.1346P] 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         3098
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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 0.31325(4) 0.42274(3) 1.08488(2) 0.02458(16) Uani 1 1 d . . .
Cl1 Cl 0.45400(12) -0.17568(10) 0.68031(8) 0.0328(2) Uani 1 1 d . . .
F1 F -0.3600(4) 1.3494(3) 0.5143(2) 0.0473(6) Uani 1 1 d . . .
F2 F -0.1356(4) 1.4198(3) 0.5657(3) 0.0696(10) Uani 1 1 d . . .
F3 F -0.3923(4) 1.4521(3) 0.6702(2) 0.0444(6) Uani 1 1 d . . .
O1 O 0.1098(3) 0.5955(3) 0.77829(18) 0.0225(5) Uani 1 1 d . . .
N1 N 0.1220(4) 0.6930(3) 0.9395(2) 0.0254(6) Uani 1 1 d . . .
C1 C 0.3143(5) 0.1657(4) 0.8874(3) 0.0268(7) Uani 1 1 d . . .
H1 H 0.3100 0.1704 0.9654 0.032 Uiso 1 1 calc R . .
C2 C 0.3741(5) 0.0169(4) 0.8473(3) 0.0274(7) Uani 1 1 d . . .
H2 H 0.4096 -0.0778 0.8978 0.033 Uiso 1 1 calc R . .
C3 C 0.3802(4) 0.0108(4) 0.7304(3) 0.0247(6) Uani 1 1 d . . .
C4 C 0.3246(5) 0.1514(4) 0.6551(3) 0.0285(7) Uani 1 1 d . . .
H4 H 0.3278 0.1460 0.5773 0.034 Uiso 1 1 calc R . .
C5 C 0.2648(5) 0.2988(4) 0.6951(3) 0.0264(7) Uani 1 1 d . . .
H5 H 0.2270 0.3927 0.6442 0.032 Uiso 1 1 calc R . .
C6 C 0.2604(4) 0.3087(4) 0.8124(3) 0.0211(6) Uani 1 1 d . . .
C7 C 0.1992(4) 0.4660(4) 0.8532(3) 0.0219(6) Uani 1 1 d . . .
C8 C 0.2073(4) 0.5285(4) 0.9496(3) 0.0220(6) Uani 1 1 d . . .
C9 C 0.0675(4) 0.7247(4) 0.8369(3) 0.0218(6) Uani 1 1 d . . .
C10 C -0.0334(4) 0.8832(4) 0.7794(3) 0.0225(6) Uani 1 1 d . . .
C11 C -0.0741(5) 1.0169(4) 0.8360(3) 0.0271(7) Uani 1 1 d . . .
H11 H -0.0456 1.0051 0.9115 0.033 Uiso 1 1 calc R . .
C12 C -0.1575(5) 1.1696(4) 0.7808(3) 0.0272(7) Uani 1 1 d . . .
H12 H -0.1850 1.2601 0.8188 0.033 Uiso 1 1 calc R . .
C13 C -0.1991(4) 1.1847(4) 0.6682(3) 0.0247(6) Uani 1 1 d . . .
C14 C -0.1645(5) 1.0516(4) 0.6118(3) 0.0290(7) Uani 1 1 d . . .
H14 H -0.1969 1.0637 0.5371 0.035 Uiso 1 1 calc R . .
C15 C -0.0809(5) 0.8986(4) 0.6667(3) 0.0267(7) Uani 1 1 d . . .
H15 H -0.0568 0.8079 0.6292 0.032 Uiso 1 1 calc R . .
C16 C -0.2717(5) 1.3512(4) 0.6044(3) 0.0317(7) Uani 1 1 d . . .

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 0.0291(2) 0.0199(2) 0.0227(2) 0.00240(13) -0.00990(13) -0.00297(14)
Cl1 0.0394(5) 0.0218(4) 0.0358(5) -0.0087(3) -0.0071(3) -0.0019(3)
F1 0.0694(16) 0.0282(11) 0.0370(12) 0.0014(9) -0.0317(11) 0.0067(11)
F2 0.0475(14) 0.0495(16) 0.100(2) 0.0451(16) -0.0199(14) -0.0182(12)
F3 0.0648(15) 0.0202(10) 0.0407(12) -0.0041(9) -0.0168(11) 0.0060(10)
O1 0.0247(10) 0.0180(10) 0.0213(10) 0.0026(8) -0.0063(8) -0.0013(8)
N1 0.0261(13) 0.0189(12) 0.0277(14) 0.0018(10) -0.0058(10) -0.0018(10)
C1 0.0321(16) 0.0216(15) 0.0231(15) 0.0009(12) -0.0077(12) -0.0009(13)
C2 0.0324(16) 0.0174(14) 0.0304(17) 0.0002(12) -0.0120(13) -0.0016(12)
C3 0.0243(15) 0.0194(14) 0.0298(16) -0.0059(12) -0.0039(12) -0.0028(12)
C4 0.0340(17) 0.0264(17) 0.0239(15) -0.0026(13) -0.0077(13) -0.0042(14)
C5 0.0335(16) 0.0206(15) 0.0224(15) 0.0011(12) -0.0052(12) -0.0037(13)
C6 0.0193(13) 0.0201(15) 0.0235(14) -0.0016(11) -0.0050(11) -0.0038(11)
C7 0.0226(14) 0.0165(14) 0.0243(15) 0.0053(11) -0.0085(11) -0.0030(11)
C8 0.0214(14) 0.0180(14) 0.0244(14) 0.0038(12) -0.0067(11) -0.0033(11)
C9 0.0208(14) 0.0192(14) 0.0225(15) 0.0023(12) -0.0019(11) -0.0034(11)
C10 0.0206(14) 0.0193(14) 0.0254(15) 0.0022(12) -0.0060(11) -0.0030(11)
C11 0.0338(17) 0.0227(16) 0.0230(15) 0.0016(13) -0.0133(13) -0.0027(13)
C12 0.0340(16) 0.0166(14) 0.0294(16) -0.0009(12) -0.0095(13) -0.0026(12)
C13 0.0235(15) 0.0201(15) 0.0276(16) 0.0049(12) -0.0083(12) -0.0030(12)
C14 0.0332(16) 0.0252(16) 0.0241(15) 0.0010(13) -0.0110(13) 0.0008(13)
C15 0.0329(16) 0.0187(15) 0.0262(16) -0.0026(12) -0.0085(12) -0.0012(12)
C16 0.0343(17) 0.0239(16) 0.0318(17) 0.0072(13) -0.0120(14) -0.0017(14)

_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 C8 1.865(3) . ?
Cl1 C3 1.735(3) . ?
F1 C16 1.329(4) . ?
F2 C16 1.329(4) . ?
F3 C16 1.344(4) . ?
O1 C9 1.357(4) . ?
O1 C7 1.381(3) . ?
N1 C9 1.295(4) . ?
N1 C8 1.384(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.398(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(5) . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(5) . ?
C7 C8 1.357(5) . ?
C9 C10 1.474(4) . ?
C10 C11 1.377(5) . ?
C10 C15 1.402(5) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(5) . ?
C13 C16 1.506(4) . ?
C14 C15 1.392(4) . ?
C14 H14 0.9300 . ?
C15 H15 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
C9 O1 C7 105.1(2) . . ?
C9 N1 C8 103.1(3) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 Cl1 120.3(3) . . ?
C2 C3 Cl1 119.2(2) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 121.5(3) . . ?
C5 C6 C7 119.8(3) . . ?
C8 C7 O1 105.5(3) . . ?
C8 C7 C6 137.4(3) . . ?
O1 C7 C6 117.0(3) . . ?
C7 C8 N1 111.4(3) . . ?
C7 C8 Br1 128.8(2) . . ?
N1 C8 Br1 119.8(2) . . ?
N1 C9 O1 114.8(3) . . ?
N1 C9 C10 127.1(3) . . ?
O1 C9 C10 118.1(3) . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 C9 119.3(3) . . ?
C15 C10 C9 120.3(3) . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 C16 119.5(3) . . ?
C12 C13 C16 119.1(3) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
F2 C16 F1 106.8(3) . . ?
F2 C16 F3 106.7(3) . . ?
F1 C16 F3 106.4(3) . . ?
F2 C16 C13 111.6(3) . . ?
F1 C16 C13 112.5(3) . . ?
F3 C16 C13 112.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         1.437
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.141
_database_code_depnum_ccdc_archive 'CCDC 964941'
