# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ki-104-a
_database_code_depnum_ccdc_archive 'CCDC 913508'
_audit_update_record             
;
2012-12-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            3a
_chemical_formula_moiety         'C17 H14 O2'
_chemical_formula_sum            'C17 H14 O2'
_chemical_compound_source        synthesized
_exptl_crystal_recrystallization_method 'slow evaporation of DCM, Hexane'
_chemical_melting_point          ?

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         250.28

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'
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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_int_tables_number      14
_chemical_absolute_configuration syn

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                   4.7273(6)
_cell_length_b                   13.5885(16)
_cell_length_c                   20.003(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.613(7)
_cell_angle_gamma                90.00
_cell_volume                     1276.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.084

_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            15245
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.76
_reflns_number_total             2500
_reflns_number_gt                1434
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2500
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.845
_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 0.4607(2) 0.59267(9) 0.12918(7) 0.0616(4) Uani 1 1 d . . .
H1 H 0.5656 0.5708 0.1028 0.092 Uiso 1 1 calc R . .
O2 O 0.8940(2) 0.59600(9) 0.05821(7) 0.0636(4) Uani 1 1 d . . .
H2 H 1.0520 0.5854 0.0784 0.095 Uiso 1 1 calc R . .
C8 C 0.7585(3) 0.73580(12) 0.12326(8) 0.0444(4) Uani 1 1 d . . .
C17 C 0.8621(3) 0.82580(12) 0.15374(9) 0.0471(5) Uani 1 1 d . . .
C12 C 0.7699(3) 0.85519(13) 0.21613(9) 0.0525(5) Uani 1 1 d . . .
C9 C 0.5700(3) 0.68044(13) 0.15573(9) 0.0487(5) Uani 1 1 d . . .
C10 C 0.4813(4) 0.70953(15) 0.21708(10) 0.0584(5) Uani 1 1 d . . .
H10 H 0.3561 0.6702 0.2379 0.070 Uiso 1 1 calc R . .
C1 C 0.6091(4) 0.72209(14) -0.00086(8) 0.0495(5) Uani 1 1 d . . .
C15 C 1.1488(4) 0.97391(16) 0.15632(11) 0.0693(6) Uani 1 1 d . . .
H15 H 1.2771 1.0135 0.1368 0.083 Uiso 1 1 calc R . .
C7 C 0.8411(3) 0.70008(13) 0.05617(8) 0.0503(5) Uani 1 1 d . . .
H7 H 1.0157 0.7340 0.0472 0.060 Uiso 1 1 calc R . .
C11 C 0.5774(4) 0.79464(16) 0.24608(10) 0.0618(5) Uani 1 1 d . . .
H11 H 0.5155 0.8138 0.2866 0.074 Uiso 1 1 calc R . .
C13 C 0.8703(4) 0.94493(17) 0.24599(10) 0.0709(6) Uani 1 1 d . . .
H13 H 0.8075 0.9646 0.2863 0.085 Uiso 1 1 calc R . .
C16 C 1.0559(4) 0.88910(13) 0.12503(10) 0.0555(5) Uani 1 1 d . . .
H16 H 1.1198 0.8722 0.0843 0.067 Uiso 1 1 calc R . .
C14 C 1.0559(5) 1.00283(16) 0.21718(13) 0.0749(6) Uani 1 1 d . . .
H14 H 1.1207 1.0613 0.2377 0.090 Uiso 1 1 calc R . .
C2 C 0.4729(4) 0.64922(16) -0.03985(10) 0.0668(6) Uani 1 1 d . . .
H2A H 0.5256 0.5839 -0.0323 0.080 Uiso 1 1 calc R . .
C6 C 0.5278(4) 0.81850(16) -0.01408(10) 0.0629(6) Uani 1 1 d . . .
H6 H 0.6177 0.8688 0.0118 0.075 Uiso 1 1 calc R . .
C5 C 0.3157(4) 0.84131(18) -0.06493(11) 0.0750(6) Uani 1 1 d . . .
H5 H 0.2654 0.9066 -0.0736 0.090 Uiso 1 1 calc R . .
C4 C 0.1785(5) 0.7673(2) -0.10288(11) 0.0794(7) Uani 1 1 d . . .
H4 H 0.0331 0.7821 -0.1368 0.095 Uiso 1 1 calc R . .
C3 C 0.2572(5) 0.6725(2) -0.09040(10) 0.0816(7) Uani 1 1 d . . .
H3 H 0.1654 0.6224 -0.1161 0.098 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
O1 0.0536(7) 0.0544(9) 0.0762(10) 0.0026(7) 0.0043(6) -0.0044(6)
O2 0.0544(8) 0.0526(9) 0.0828(10) -0.0075(7) 0.0035(7) 0.0097(6)
C8 0.0348(8) 0.0489(11) 0.0481(10) 0.0031(8) -0.0014(7) 0.0057(7)
C17 0.0365(9) 0.0487(12) 0.0536(11) 0.0010(9) -0.0057(7) 0.0071(7)
C12 0.0484(10) 0.0560(13) 0.0500(11) -0.0032(10) -0.0076(8) 0.0147(9)
C9 0.0406(9) 0.0467(12) 0.0568(12) 0.0063(9) -0.0029(8) 0.0044(8)
C10 0.0515(11) 0.0679(15) 0.0560(12) 0.0160(11) 0.0081(9) 0.0065(9)
C1 0.0442(9) 0.0601(13) 0.0453(11) -0.0020(9) 0.0102(8) -0.0002(8)
C15 0.0519(11) 0.0597(14) 0.0918(17) 0.0027(12) -0.0101(11) -0.0041(9)
C7 0.0427(10) 0.0475(13) 0.0605(12) -0.0022(9) 0.0054(8) 0.0000(8)
C11 0.0586(12) 0.0773(15) 0.0495(12) 0.0036(11) 0.0060(9) 0.0182(10)
C13 0.0724(14) 0.0725(16) 0.0625(14) -0.0154(12) -0.0153(11) 0.0197(12)
C16 0.0455(10) 0.0520(13) 0.0674(12) 0.0016(10) -0.0009(9) -0.0003(8)
C14 0.0709(14) 0.0559(15) 0.0907(17) -0.0175(12) -0.0213(12) 0.0038(11)
C2 0.0740(13) 0.0711(14) 0.0540(12) -0.0071(11) 0.0010(10) -0.0032(11)
C6 0.0535(11) 0.0696(16) 0.0644(13) 0.0013(11) 0.0014(10) -0.0022(10)
C5 0.0678(13) 0.0840(18) 0.0718(15) 0.0139(13) 0.0023(12) 0.0087(12)
C4 0.0626(13) 0.119(2) 0.0546(14) 0.0107(14) -0.0025(10) 0.0009(14)
C3 0.0839(16) 0.104(2) 0.0537(14) -0.0112(13) -0.0065(12) -0.0145(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 1.381(2) . ?
O2 C7 1.436(2) . ?
C8 C9 1.384(2) . ?
C8 C17 1.428(2) . ?
C8 C7 1.520(2) . ?
C17 C16 1.425(2) . ?
C17 C12 1.426(2) . ?
C12 C11 1.411(2) . ?
C12 C13 1.416(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.349(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.382(2) . ?
C1 C7 1.518(2) . ?
C15 C16 1.360(2) . ?
C15 C14 1.397(3) . ?
C13 C14 1.355(3) . ?
C2 C3 1.387(3) . ?
C6 C5 1.379(3) . ?
C5 C4 1.377(3) . ?
C4 C3 1.355(3) . ?

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 C8 C17 118.23(16) . . ?
C9 C8 C7 119.05(16) . . ?
C17 C8 C7 122.70(14) . . ?
C16 C17 C12 117.35(17) . . ?
C16 C17 C8 123.36(16) . . ?
C12 C17 C8 119.29(15) . . ?
C11 C12 C13 121.65(19) . . ?
C11 C12 C17 119.06(18) . . ?
C13 C12 C17 119.28(17) . . ?
O1 C9 C8 121.43(16) . . ?
O1 C9 C10 116.39(16) . . ?
C8 C9 C10 122.17(18) . . ?
C11 C10 C9 119.96(17) . . ?
C2 C1 C6 118.23(18) . . ?
C2 C1 C7 122.35(17) . . ?
C6 C1 C7 119.42(17) . . ?
C16 C15 C14 121.5(2) . . ?
O2 C7 C1 108.89(14) . . ?
O2 C7 C8 110.56(14) . . ?
C1 C7 C8 111.33(13) . . ?
C10 C11 C12 121.28(17) . . ?
C14 C13 C12 121.51(19) . . ?
C15 C16 C17 120.98(18) . . ?
C13 C14 C15 119.4(2) . . ?
C1 C2 C3 120.4(2) . . ?
C5 C6 C1 121.1(2) . . ?
C4 C5 C6 119.9(2) . . ?
C3 C4 C5 119.4(2) . . ?
C4 C3 C2 121.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.831
_diffrn_reflns_theta_full        27.76
_diffrn_measured_fraction_theta_full 0.831
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_ki-113
_database_code_depnum_ccdc_archive 'CCDC 913509'
_audit_update_record             
;
2012-12-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            2n
_chemical_formula_moiety         'C18 H15 Br O2'
_chemical_formula_sum            'C18 H15 Br O2'
_chemical_compound_source        synthesized
_exptl_crystal_recrystallization_method 'slow evaporation of DCM, chloroform'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         343.20

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'
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'
_symmetry_int_tables_number      14
_chemical_absolute_configuration syn

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                   13.1085(6)
_cell_length_b                   7.3865(4)
_cell_length_c                   16.4008(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.548(3)
_cell_angle_gamma                90.00
_cell_volume                     1514.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      19.81
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.0
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            18573
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.1258
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         28.59
_reflns_number_total             3866
_reflns_number_gt                1393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0412P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3593
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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 0.36927(4) 0.52673(8) 0.18144(3) 0.0899(3) Uani 1 1 d . . .
C12 C 0.3631(3) 0.4100(6) 0.4266(2) 0.0431(10) Uani 1 1 d . . .
C9 C 0.2686(3) 0.2799(5) 0.5950(2) 0.0476(10) Uani 1 1 d . . .
C17 C 0.3543(3) 0.4980(5) 0.3499(2) 0.0486(10) Uani 1 1 d . . .
H17 H 0.3297 0.6167 0.3413 0.058 Uiso 1 1 calc R . .
C11 C 0.3302(3) 0.5022(5) 0.4981(2) 0.0439(10) Uani 1 1 d . . .
H11 H 0.3932 0.5117 0.5487 0.053 Uiso 1 1 calc R . .
C10 C 0.2448(3) 0.3918(5) 0.5212(2) 0.0438(10) Uani 1 1 d . . .
C16 C 0.3830(3) 0.4058(7) 0.2862(2) 0.0530(11) Uani 1 1 d . . .
C14 C 0.4313(3) 0.1475(7) 0.3737(3) 0.0709(13) Uani 1 1 d . . .
H14 H 0.4573 0.0296 0.3821 0.085 Uiso 1 1 calc R . .
C18 C 0.2758(3) 0.7907(6) 0.5362(2) 0.0669(13) Uani 1 1 d . . .
H18A H 0.2202 0.7381 0.5555 0.100 Uiso 1 1 calc R . .
H18B H 0.2548 0.9099 0.5143 0.100 Uiso 1 1 calc R . .
H18C H 0.3406 0.7980 0.5831 0.100 Uiso 1 1 calc R . .
C8 C 0.3730(3) 0.2627(6) 0.6540(2) 0.0600(12) Uani 1 1 d . . .
H8 H 0.4295 0.3270 0.6446 0.072 Uiso 1 1 calc R . .
C6 C 0.3074(7) 0.0551(7) 0.7396(4) 0.099(2) Uani 1 1 d . . .
H6 H 0.3202 -0.0201 0.7871 0.119 Uiso 1 1 calc R . .
C15 C 0.4220(3) 0.2353(8) 0.2971(2) 0.0659(13) Uani 1 1 d . . .
H15 H 0.4422 0.1779 0.2540 0.079 Uiso 1 1 calc R . .
C4 C 0.1853(4) 0.1797(6) 0.6123(3) 0.0659(13) Uani 1 1 d . . .
C5 C 0.2070(6) 0.0706(7) 0.6845(4) 0.0987(19) Uani 1 1 d . . .
H5 H 0.1514 0.0066 0.6954 0.118 Uiso 1 1 calc R . .
C3 C 0.0803(4) 0.1935(7) 0.5537(3) 0.0801(17) Uani 1 1 d . . .
H3 H 0.0249 0.1273 0.5637 0.096 Uiso 1 1 calc R . .
C7 C 0.3919(4) 0.1532(7) 0.7244(3) 0.0815(15) Uani 1 1 d . . .
H7 H 0.4606 0.1438 0.7623 0.098 Uiso 1 1 calc R . .
C13 C 0.4018(3) 0.2354(6) 0.4379(2) 0.0562(11) Uani 1 1 d . . .
H13 H 0.4082 0.1758 0.4892 0.067 Uiso 1 1 calc R . .
C2 C 0.0600(3) 0.2995(7) 0.4848(3) 0.0714(14) Uani 1 1 d . . .
H2 H -0.0093 0.3055 0.4476 0.086 Uiso 1 1 calc R . .
C1 C 0.1404(3) 0.4015(6) 0.4675(3) 0.0539(11) Uani 1 1 d . . .
O2 O 0.29370(19) 0.6801(4) 0.46989(14) 0.0525(7) Uani 1 1 d . . .
O1 O 0.1099(2) 0.5082(4) 0.39626(17) 0.0685(9) Uani 1 1 d . . .
H1 H 0.1570 0.5824 0.3980 0.103 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 0.0963(4) 0.1294(6) 0.0529(3) 0.0153(3) 0.0360(3) 0.0166(4)
C12 0.039(2) 0.048(3) 0.044(2) -0.002(2) 0.0150(18) -0.001(2)
C9 0.070(3) 0.040(3) 0.045(2) -0.007(2) 0.036(2) -0.002(2)
C17 0.044(2) 0.052(3) 0.051(2) 0.004(2) 0.0168(17) 0.002(2)
C11 0.048(2) 0.042(3) 0.043(2) 0.000(2) 0.0145(17) 0.003(2)
C10 0.044(2) 0.049(3) 0.044(2) -0.012(2) 0.0208(19) -0.009(2)
C16 0.049(2) 0.065(3) 0.049(2) 0.002(2) 0.020(2) 0.007(2)
C14 0.068(3) 0.070(4) 0.078(3) -0.005(3) 0.026(3) 0.021(3)
C18 0.084(3) 0.051(3) 0.073(3) -0.013(2) 0.034(2) -0.001(2)
C8 0.087(3) 0.054(3) 0.048(2) 0.003(2) 0.032(2) 0.006(3)
C6 0.195(6) 0.049(4) 0.081(4) 0.012(3) 0.082(4) 0.013(5)
C15 0.060(3) 0.088(4) 0.056(3) -0.009(3) 0.026(2) 0.011(3)
C4 0.105(4) 0.043(3) 0.071(3) -0.011(2) 0.060(3) -0.010(3)
C5 0.162(6) 0.059(4) 0.108(5) -0.009(4) 0.091(5) -0.020(4)
C3 0.094(4) 0.060(4) 0.115(4) -0.036(3) 0.076(4) -0.033(3)
C7 0.129(4) 0.064(4) 0.052(3) 0.001(3) 0.029(3) 0.020(3)
C13 0.058(3) 0.062(3) 0.054(3) 0.006(2) 0.024(2) 0.010(2)
C2 0.056(3) 0.076(4) 0.093(4) -0.036(3) 0.039(3) -0.022(3)
C1 0.054(3) 0.052(3) 0.064(3) -0.016(2) 0.030(2) -0.010(2)
O2 0.0654(17) 0.044(2) 0.0539(16) -0.0038(14) 0.0270(14) 0.0039(15)
O1 0.0560(17) 0.085(3) 0.0587(18) -0.0020(17) 0.0087(14) 0.0014(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 C16 1.897(4) . ?
C12 C13 1.378(5) . ?
C12 C17 1.390(5) . ?
C12 C11 1.525(5) . ?
C9 C4 1.417(5) . ?
C9 C10 1.420(5) . ?
C9 C8 1.425(5) . ?
C17 C16 1.390(5) . ?
C11 O2 1.428(4) . ?
C11 C10 1.523(5) . ?
C10 C1 1.388(5) . ?
C16 C15 1.350(6) . ?
C14 C15 1.386(5) . ?
C14 C13 1.389(5) . ?
C18 O2 1.434(4) . ?
C8 C7 1.370(5) . ?
C6 C5 1.358(8) . ?
C6 C7 1.407(7) . ?
C4 C5 1.389(6) . ?
C4 C3 1.425(6) . ?
C3 C2 1.334(6) . ?
C2 C1 1.392(5) . ?
C1 O1 1.366(5) . ?

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
C13 C12 C17 119.1(3) . . ?
C13 C12 C11 119.5(3) . . ?
C17 C12 C11 121.5(4) . . ?
C4 C9 C10 119.4(4) . . ?
C4 C9 C8 117.2(4) . . ?
C10 C9 C8 123.4(3) . . ?
C12 C17 C16 118.9(4) . . ?
O2 C11 C10 111.9(3) . . ?
O2 C11 C12 107.8(3) . . ?
C10 C11 C12 110.6(3) . . ?
C1 C10 C9 119.5(3) . . ?
C1 C10 C11 118.2(3) . . ?
C9 C10 C11 122.3(3) . . ?
C15 C16 C17 122.3(4) . . ?
C15 C16 Br1 119.2(3) . . ?
C17 C16 Br1 118.5(3) . . ?
C15 C14 C13 120.0(4) . . ?
C7 C8 C9 121.2(4) . . ?
C5 C6 C7 119.7(5) . . ?
C16 C15 C14 118.9(4) . . ?
C5 C4 C9 120.1(5) . . ?
C5 C4 C3 121.7(5) . . ?
C9 C4 C3 118.2(4) . . ?
C6 C5 C4 121.7(6) . . ?
C2 C3 C4 121.2(4) . . ?
C8 C7 C6 120.1(5) . . ?
C12 C13 C14 120.8(4) . . ?
C3 C2 C1 121.3(5) . . ?
O1 C1 C10 123.4(3) . . ?
O1 C1 C2 116.3(4) . . ?
C10 C1 C2 120.3(4) . . ?
C11 O2 C18 113.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        28.59
_diffrn_measured_fraction_theta_full 0.929
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.059



