# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_test_12_0m
_database_code_depnum_ccdc_archive 'CCDC 1465239'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cl2 O4'
_chemical_formula_weight         329.16

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   13.0766(3)
_cell_length_b                   8.0857(2)
_cell_length_c                   14.0760(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.350(2)
_cell_angle_gamma                90.00
_cell_volume                     1488.28(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4447
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8699
_exptl_absorpt_correction_T_max  0.8924
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  '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            10026
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         27.55
_reflns_number_total             3393
_reflns_number_gt                2766
_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    '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)+(0.0517P)²+0.2552P] 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         3393
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C13 C 0.13800(18) 0.6400(3) 0.02150(15) 0.0525(5) Uani 1 1 d . . .
Cl1 Cl 0.22388(3) 1.08268(6) -0.00783(3) 0.04437(14) Uani 1 1 d . . .
Cl2 Cl 0.07727(4) 1.28340(6) 0.13034(4) 0.05199(15) Uani 1 1 d . . .
O3 O 0.23346(8) 0.81975(13) 0.22655(7) 0.0316(2) Uani 1 1 d . . .
O1 O 0.24512(9) 1.17184(17) 0.30398(8) 0.0457(3) Uani 1 1 d . . .
O2 O 0.08563(9) 1.10660(17) 0.33054(9) 0.0495(3) Uani 1 1 d . . .
C7 C 0.23241(10) 1.03833(18) 0.11577(10) 0.0269(3) Uani 1 1 d . . .
C6 C 0.33132(11) 1.09663(18) 0.15726(12) 0.0316(3) Uani 1 1 d . . .
C8 C 0.13547(11) 1.09647(18) 0.16800(11) 0.0296(3) Uani 1 1 d . . .
O4 O 0.31370(10) 0.70158(17) 0.05610(11) 0.0576(4) Uani 1 1 d . . .
C12 C 0.21114(13) 0.7244(2) 0.06457(11) 0.0361(4) Uani 1 1 d . . .
C11 C 0.19195(10) 0.85726(18) 0.13561(10) 0.0278(3) Uani 1 1 d . . .
C9 C 0.15229(12) 1.12102(19) 0.27389(11) 0.0340(3) Uani 1 1 d . . .
C5 C 0.33221(12) 1.1615(2) 0.24741(12) 0.0383(4) Uani 1 1 d . . .
C10 C 0.08336(11) 0.9317(2) 0.14554(12) 0.0340(3) Uani 1 1 d . . .
H10A H 0.0438 0.9320 0.0870 0.041 Uiso 1 1 calc R . .
H10B H 0.0443 0.8864 0.1978 0.041 Uiso 1 1 calc R . .
C1 C 0.42387(13) 1.0892(2) 0.10899(15) 0.0455(4) Uani 1 1 d . . .
H1A H 0.4258 1.0453 0.0480 0.055 Uiso 1 1 calc R . .
C14 C 0.19505(15) 0.6705(2) 0.26767(14) 0.0482(4) Uani 1 1 d . . .
H14A H 0.2262 0.6537 0.3288 0.072 Uiso 1 1 calc R . .
H14B H 0.2109 0.5787 0.2270 0.072 Uiso 1 1 calc R . .
H14C H 0.1223 0.6788 0.2747 0.072 Uiso 1 1 calc R . .
C4 C 0.42098(15) 1.2192(3) 0.29039(16) 0.0584(5) Uani 1 1 d . . .
H4A H 0.4195 1.2625 0.3516 0.070 Uiso 1 1 calc R . .
C3 C 0.51122(16) 1.2113(3) 0.2411(2) 0.0696(7) Uani 1 1 d . . .
H3A H 0.5714 1.2500 0.2688 0.083 Uiso 1 1 calc R . .
C2 C 0.51274(14) 1.1465(3) 0.15109(19) 0.0618(6) Uani 1 1 d . . .
H2A H 0.5741 1.1411 0.1181 0.074 Uiso 1 1 calc R . .
C15 C 0.3452(2) 0.5598(3) 0.0035(3) 0.0949(10) Uani 1 1 d . . .
H15A H 0.4185 0.5559 0.0015 0.142 Uiso 1 1 calc R . .
H15B H 0.3184 0.5665 -0.0600 0.142 Uiso 1 1 calc R . .
H15C H 0.3199 0.4617 0.0336 0.142 Uiso 1 1 calc R . .
H13A H 0.1516(17) 0.555(3) -0.0212(17) 0.067(7) Uiso 1 1 d . . .
H13B H 0.0668(19) 0.672(3) 0.0371(17) 0.067(7) Uiso 1 1 d . . .


_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
C13 C12 1.320(3) . ?
Cl1 C7 1.7792(14) . ?
Cl2 C8 1.7719(15) . ?
O3 C11 1.4201(17) . ?
O3 C14 1.431(2) . ?
O1 C9 1.3474(19) . ?
O1 C5 1.396(2) . ?
O2 C9 1.1908(19) . ?
C7 C6 1.492(2) . ?
C7 C8 1.5427(19) . ?
C7 C11 1.582(2) . ?
C6 C5 1.373(2) . ?
C6 C1 1.393(2) . ?
C8 C9 1.518(2) . ?
C8 C10 1.528(2) . ?
O4 C12 1.360(2) . ?
O4 C15 1.427(3) . ?
C12 C11 1.490(2) . ?
C11 C10 1.549(2) . ?
C5 C4 1.387(2) . ?
C1 C2 1.381(3) . ?
C4 C3 1.374(3) . ?
C3 C2 1.371(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
C11 O3 C14 114.30(12) . . ?
C9 O1 C5 122.61(12) . . ?
C6 C7 C8 115.46(12) . . ?
C6 C7 C11 120.88(12) . . ?
C8 C7 C11 85.48(10) . . ?
C6 C7 Cl1 111.60(10) . . ?
C8 C7 Cl1 110.96(10) . . ?
C11 C7 Cl1 109.88(10) . . ?
C5 C6 C1 117.70(15) . . ?
C5 C6 C7 119.00(13) . . ?
C1 C6 C7 123.30(15) . . ?
C9 C8 C10 112.25(13) . . ?
C9 C8 C7 113.15(12) . . ?
C10 C8 C7 90.14(11) . . ?
C9 C8 Cl2 103.98(10) . . ?
C10 C8 Cl2 119.43(10) . . ?
C7 C8 Cl2 118.04(10) . . ?
C12 O4 C15 116.28(17) . . ?
C13 C12 O4 127.00(18) . . ?
C13 C12 C11 123.84(17) . . ?
O4 C12 C11 109.09(13) . . ?
O3 C11 C12 112.71(12) . . ?
O3 C11 C10 110.31(12) . . ?
C12 C11 C10 119.93(13) . . ?
O3 C11 C7 103.32(11) . . ?
C12 C11 C7 119.38(12) . . ?
C10 C11 C7 87.93(10) . . ?
O2 C9 O1 118.76(15) . . ?
O2 C9 C8 122.85(14) . . ?
O1 C9 C8 118.25(13) . . ?
C6 C5 C4 122.28(16) . . ?
C6 C5 O1 123.21(14) . . ?
C4 C5 O1 114.50(16) . . ?
C8 C10 C11 87.12(10) . . ?
C2 C1 C6 120.50(19) . . ?
C3 C4 C5 118.9(2) . . ?
C2 C3 C4 120.11(18) . . ?
C3 C2 C1 120.50(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C7 C6 C5 14.9(2) . . . . ?
C11 C7 C6 C5 -85.60(19) . . . . ?
Cl1 C7 C6 C5 142.87(13) . . . . ?
C8 C7 C6 C1 -164.90(15) . . . . ?
C11 C7 C6 C1 94.56(19) . . . . ?
Cl1 C7 C6 C1 -36.96(19) . . . . ?
C6 C7 C8 C9 -30.60(17) . . . . ?
C11 C7 C8 C9 91.58(13) . . . . ?
Cl1 C7 C8 C9 -158.85(10) . . . . ?
C6 C7 C8 C10 -144.99(13) . . . . ?
C11 C7 C8 C10 -22.81(10) . . . . ?
Cl1 C7 C8 C10 86.77(11) . . . . ?
C6 C7 C8 Cl2 91.09(14) . . . . ?
C11 C7 C8 Cl2 -146.73(11) . . . . ?
Cl1 C7 C8 Cl2 -37.16(14) . . . . ?
C15 O4 C12 C13 -7.5(3) . . . . ?
C15 O4 C12 C11 169.5(2) . . . . ?
C14 O3 C11 C12 -58.88(16) . . . . ?
C14 O3 C11 C10 78.14(16) . . . . ?
C14 O3 C11 C7 170.90(13) . . . . ?
C13 C12 C11 O3 118.07(18) . . . . ?
O4 C12 C11 O3 -59.07(17) . . . . ?
C13 C12 C11 C10 -14.4(2) . . . . ?
O4 C12 C11 C10 168.46(14) . . . . ?
C13 C12 C11 C7 -120.45(18) . . . . ?
O4 C12 C11 C7 62.42(18) . . . . ?
C6 C7 C11 O3 29.19(16) . . . . ?
C8 C7 C11 O3 -87.89(11) . . . . ?
Cl1 C7 C11 O3 161.43(9) . . . . ?
C6 C7 C11 C12 -96.87(17) . . . . ?
C8 C7 C11 C12 146.05(13) . . . . ?
Cl1 C7 C11 C12 35.37(15) . . . . ?
C6 C7 C11 C10 139.58(13) . . . . ?
C8 C7 C11 C10 22.50(11) . . . . ?
Cl1 C7 C11 C10 -88.17(11) . . . . ?
C5 O1 C9 O2 167.12(16) . . . . ?
C5 O1 C9 C8 -17.2(2) . . . . ?
C10 C8 C9 O2 -51.9(2) . . . . ?
C7 C8 C9 O2 -152.17(15) . . . . ?
Cl2 C8 C9 O2 78.54(18) . . . . ?
C10 C8 C9 O1 132.54(14) . . . . ?
C7 C8 C9 O1 32.30(19) . . . . ?
Cl2 C8 C9 O1 -96.99(14) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C7 C6 C5 C4 -179.54(17) . . . . ?
C1 C6 C5 O1 -178.33(16) . . . . ?
C7 C6 C5 O1 1.8(2) . . . . ?
C9 O1 C5 C6 -1.1(3) . . . . ?
C9 O1 C5 C4 -179.80(17) . . . . ?
C9 C8 C10 C11 -91.92(13) . . . . ?
C7 C8 C10 C11 23.28(11) . . . . ?
Cl2 C8 C10 C11 146.03(11) . . . . ?
O3 C11 C10 C8 80.76(13) . . . . ?
C12 C11 C10 C8 -145.75(14) . . . . ?
C7 C11 C10 C8 -22.68(11) . . . . ?
C5 C6 C1 C2 -0.4(3) . . . . ?
C7 C6 C1 C2 179.47(17) . . . . ?
C6 C5 C4 C3 0.0(3) . . . . ?
O1 C5 C4 C3 178.8(2) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C4 C3 C2 C1 0.2(4) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1495697'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 Br O2'
_chemical_formula_weight         303.15

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'
Br Br -0.2901 2.4595 '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           Triclinic
_symmetry_space_group_name_H-M   P-1


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8650(11)
_cell_length_b                   8.6070(11)
_cell_length_c                   10.2615(15)
_cell_angle_alpha                92.788(6)
_cell_angle_beta                 112.186(6)
_cell_angle_gamma                105.046(4)
_cell_volume                     612.75(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2736
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.29

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    3.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7888
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.44
_reflns_number_total             2718
_reflns_number_gt                2111
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0614P)²+0.1003P] 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         2718
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.35160(5) 1.31383(4) 0.54300(3) 0.05132(16) Uani 1 1 d . . .
O1 O 0.8379(3) 1.0421(3) 0.3213(2) 0.0467(5) Uani 1 1 d . . .
O2 O 0.8879(3) 0.8844(3) 0.1753(3) 0.0599(7) Uani 1 1 d . . .
C2 C 0.4994(5) 1.2234(4) 0.4702(3) 0.0396(7) Uani 1 1 d . . .
C9 C 0.7694(5) 0.9254(4) 0.2036(3) 0.0428(7) Uani 1 1 d . . .
C1 C 0.4101(4) 1.1109(3) 0.3476(3) 0.0370(6) Uani 1 1 d . . .
H1A H 0.2766 1.0785 0.3005 0.044 Uiso 1 1 calc R . .
C7 C 0.4366(4) 0.9206(3) 0.1653(3) 0.0343(6) Uani 1 1 d . . .
C6 C 0.5184(4) 1.0446(3) 0.2929(3) 0.0345(6) Uani 1 1 d . . .
C11 C 0.2921(5) 0.6758(4) -0.0746(3) 0.0435(7) Uani 1 1 d . . .
C13 C 0.2396(4) 0.8553(4) 0.0843(3) 0.0387(7) Uani 1 1 d . . .
H13A H 0.1547 0.8930 0.1106 0.046 Uiso 1 1 calc R . .
C8 C 0.5612(4) 0.8627(4) 0.1241(3) 0.0385(7) Uani 1 1 d . . .
C10 C 0.4880(5) 0.7409(4) 0.0048(3) 0.0438(7) Uani 1 1 d . . .
H10A H 0.5728 0.7031 -0.0216 0.053 Uiso 1 1 calc R . .
C3 C 0.6991(5) 1.2725(4) 0.5442(4) 0.0469(8) Uani 1 1 d . . .
H3A H 0.7582 1.3480 0.6280 0.056 Uiso 1 1 calc R . .
C12 C 0.1669(4) 0.7363(4) -0.0340(3) 0.0396(7) Uani 1 1 d . . .
C5 C 0.7179(4) 1.0978(4) 0.3671(3) 0.0388(7) Uani 1 1 d . . .
C4 C 0.8065(5) 1.2082(4) 0.4921(4) 0.0488(8) Uani 1 1 d . . .
H4A H 0.9397 1.2390 0.5410 0.059 Uiso 1 1 calc R . .
C14 C -0.0488(5) 0.6704(5) -0.1181(4) 0.0569(9) Uani 1 1 d . . .
H14A H -0.1121 0.7244 -0.0754 0.085 Uiso 1 1 calc R . .
H14B H -0.0905 0.5553 -0.1177 0.085 Uiso 1 1 calc R . .
H14C H -0.0805 0.6896 -0.2147 0.085 Uiso 1 1 calc R . .
C15 C 0.2186(6) 0.5425(5) -0.2010(4) 0.0595(10) Uani 1 1 d . . .
H15A H 0.0804 0.5102 -0.2439 0.089 Uiso 1 1 calc R . .
H15B H 0.2609 0.4504 -0.1699 0.089 Uiso 1 1 calc R . .
H15C H 0.2676 0.5821 -0.2696 0.089 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.894(3) . ?
O1 C9 1.367(4) . ?
O1 C5 1.374(4) . ?
O2 C9 1.201(4) . ?
C2 C1 1.369(4) . ?
C2 C3 1.394(5) . ?
C9 C8 1.458(5) . ?
C1 C6 1.395(4) . ?
C1 H1A 0.9300 . ?
C7 C8 1.391(4) . ?
C7 C13 1.392(4) . ?
C7 C6 1.462(4) . ?
C6 C5 1.394(4) . ?
C11 C10 1.382(5) . ?
C11 C12 1.403(4) . ?
C11 C15 1.509(4) . ?
C13 C12 1.379(4) . ?
C13 H13A 0.9300 . ?
C8 C10 1.399(4) . ?
C10 H10A 0.9300 . ?
C3 C4 1.364(5) . ?
C3 H3A 0.9300 . ?
C12 C14 1.514(5) . ?
C5 C4 1.378(4) . ?
C4 H4A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 C5 122.3(2) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 Br1 120.0(2) . . ?
C3 C2 Br1 118.8(2) . . ?
O2 C9 O1 116.3(3) . . ?
O2 C9 C8 126.1(3) . . ?
O1 C9 C8 117.6(3) . . ?
C2 C1 C6 120.3(3) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C8 C7 C13 118.2(3) . . ?
C8 C7 C6 118.5(3) . . ?
C13 C7 C6 123.2(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 117.9(3) . . ?
C1 C6 C7 124.5(3) . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 C15 119.7(3) . . ?
C12 C11 C15 121.9(3) . . ?
C12 C13 C7 121.8(3) . . ?
C12 C13 H13A 119.1 . . ?
C7 C13 H13A 119.1 . . ?
C7 C8 C10 120.2(3) . . ?
C7 C8 C9 121.4(3) . . ?
C10 C8 C9 118.5(3) . . ?
C11 C10 C8 121.3(3) . . ?
C11 C10 H10A 119.3 . . ?
C8 C10 H10A 119.3 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 C14 119.3(3) . . ?
C11 C12 C14 120.5(3) . . ?
O1 C5 C4 115.9(3) . . ?
O1 C5 C6 122.3(3) . . ?
C4 C5 C6 121.8(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C9 O2 -178.8(3) . . . . ?
C5 O1 C9 C8 1.5(4) . . . . ?
C3 C2 C1 C6 -1.0(5) . . . . ?
Br1 C2 C1 C6 179.6(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 178.2(3) . . . . ?
C8 C7 C6 C5 -0.3(4) . . . . ?
C13 C7 C6 C5 178.5(3) . . . . ?
C8 C7 C6 C1 -178.8(3) . . . . ?
C13 C7 C6 C1 0.1(4) . . . . ?
C8 C7 C13 C12 0.1(4) . . . . ?
C6 C7 C13 C12 -178.8(3) . . . . ?
C13 C7 C8 C10 -0.6(4) . . . . ?
C6 C7 C8 C10 178.3(3) . . . . ?
C13 C7 C8 C9 179.9(3) . . . . ?
C6 C7 C8 C9 -1.2(4) . . . . ?
O2 C9 C8 C7 -179.1(3) . . . . ?
O1 C9 C8 C7 0.7(4) . . . . ?
O2 C9 C8 C10 1.4(5) . . . . ?
O1 C9 C8 C10 -178.8(3) . . . . ?
C12 C11 C10 C8 0.9(5) . . . . ?
C15 C11 C10 C8 -178.9(3) . . . . ?
C7 C8 C10 C11 0.1(5) . . . . ?
C9 C8 C10 C11 179.6(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
Br1 C2 C3 C4 -179.8(3) . . . . ?
C7 C13 C12 C11 1.0(5) . . . . ?
C7 C13 C12 C14 -179.8(3) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C15 C11 C12 C13 178.4(3) . . . . ?
C10 C11 C12 C14 179.4(3) . . . . ?
C15 C11 C12 C14 -0.8(5) . . . . ?
C9 O1 C5 C4 176.1(3) . . . . ?
C9 O1 C5 C6 -3.1(4) . . . . ?
C1 C6 C5 O1 -179.0(3) . . . . ?
C7 C6 C5 O1 2.4(4) . . . . ?
C1 C6 C5 C4 1.8(4) . . . . ?
C7 C6 C5 C4 -176.8(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
O1 C5 C4 C3 178.7(3) . . . . ?
C6 C5 C4 C3 -2.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.079
