# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_dm14320
_database_code_depnum_ccdc_archive 'CCDC 1048128'
_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Cl O3'
_chemical_formula_weight         236.64

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.632(2)
_cell_length_b                   9.726(2)
_cell_length_c                   11.729(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1098.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4191
_cell_measurement_theta_min      5.438
_cell_measurement_theta_max      55.190

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4633
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7270
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.721
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2040
_reflns_number_gt                1898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.8707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2040
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90282(13) 0.67093(11) 0.29444(11) 0.0441(4) Uani 1 1 d . . . . .
O1 O 0.6758(3) 0.6657(3) 0.4651(2) 0.0354(7) Uani 1 1 d . . . . .
O2 O 0.9713(4) 0.4130(4) 0.4098(3) 0.0476(9) Uani 1 1 d . . . . .
O3 O 0.7521(4) 0.3481(3) 0.4391(3) 0.0373(8) Uani 1 1 d . . . . .
C1 C 0.5004(5) 0.4934(4) 0.2343(3) 0.0289(9) Uani 1 1 d . . . . .
C2 C 0.3672(5) 0.4690(4) 0.1947(4) 0.0344(10) Uani 1 1 d . . . . .
H2 H 0.3545 0.4221 0.1244 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2517(6) 0.5119(5) 0.2562(4) 0.0381(11) Uani 1 1 d . . . . .
H3 H 0.1610 0.4931 0.2285 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2693(5) 0.5821(5) 0.3577(4) 0.0354(10) Uani 1 1 d . . . . .
H4 H 0.1906 0.6125 0.3996 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4013(5) 0.6078(4) 0.3981(3) 0.0313(9) Uani 1 1 d . . . . .
H5 H 0.4128 0.6557 0.4681 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5174(5) 0.5649(4) 0.3380(3) 0.0262(9) Uani 1 1 d . . . . .
C7 C 0.6564(5) 0.5955(4) 0.3817(3) 0.0268(9) Uani 1 1 d . . . . .
C8 C 0.7818(5) 0.5343(4) 0.3189(4) 0.0328(10) Uani 1 1 d . . . . .
C9 C 0.7508(5) 0.4674(4) 0.2070(4) 0.0334(10) Uani 1 1 d . . . . .
H9 H 0.8257 0.4378 0.1604 0.040 Uiso 1 1 calc R U . . .
C10 C 0.6222(5) 0.4481(4) 0.1713(4) 0.0329(10) Uani 1 1 d . . . . .
H10 H 0.6085 0.4022 0.1006 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8509(5) 0.4257(5) 0.3953(4) 0.0307(9) Uani 1 1 d . . . . .
C12 C 0.7974(6) 0.2321(5) 0.5076(5) 0.0449(13) Uani 1 1 d . . . . .
H12A H 0.8509 0.2656 0.5731 0.067 Uiso 1 1 calc R U . . .
H12B H 0.8558 0.1715 0.4613 0.067 Uiso 1 1 calc R U . . .
H12C H 0.7162 0.1811 0.5348 0.067 Uiso 1 1 calc R U . . .


_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
Cl1 C8 1.791(5) . ?
O1 C7 1.208(5) . ?
O2 C11 1.178(5) . ?
O3 C11 1.318(6) . ?
O3 C12 1.452(6) . ?
C1 C2 1.386(7) . ?
C1 C6 1.410(5) . ?
C1 C10 1.455(6) . ?
C2 C3 1.389(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.464(6) . ?
C7 C8 1.534(6) . ?
C8 C9 1.495(6) . ?
C8 C11 1.537(6) . ?
C9 C10 1.321(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 C12 116.3(4) . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 C10 121.6(4) . . ?
C6 C1 C10 119.6(4) . . ?
C1 C2 C3 121.1(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.6(4) . . ?
C5 C6 C7 119.9(4) . . ?
C1 C6 C7 120.5(4) . . ?
O1 C7 C6 122.7(4) . . ?
O1 C7 C8 119.1(4) . . ?
C6 C7 C8 118.2(4) . . ?
C9 C8 C7 115.7(4) . . ?
C9 C8 C11 107.4(3) . . ?
C7 C8 C11 109.1(3) . . ?
C9 C8 Cl1 108.2(3) . . ?
C7 C8 Cl1 107.6(3) . . ?
C11 C8 Cl1 108.8(3) . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C1 123.5(4) . . ?
C9 C10 H10 118.3 . . ?
C1 C10 H10 118.3 . . ?
O2 C11 O3 126.4(5) . . ?
O2 C11 C8 125.6(5) . . ?
O3 C11 C8 108.0(4) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 C1 C2 C3 -0.9(6) . . . . ?
C10 C1 C2 C3 179.5(4) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C10 C1 C6 C5 -179.9(4) . . . . ?
C2 C1 C6 C7 -178.7(4) . . . . ?
C10 C1 C6 C7 0.9(6) . . . . ?
C5 C6 C7 O1 -5.3(6) . . . . ?
C1 C6 C7 O1 173.9(4) . . . . ?
C5 C6 C7 C8 174.2(4) . . . . ?
C1 C6 C7 C8 -6.6(6) . . . . ?
O1 C7 C8 C9 -170.9(4) . . . . ?
C6 C7 C8 C9 9.6(5) . . . . ?
O1 C7 C8 C11 68.0(5) . . . . ?
C6 C7 C8 C11 -111.5(4) . . . . ?
O1 C7 C8 Cl1 -49.8(5) . . . . ?
C6 C7 C8 Cl1 130.7(3) . . . . ?
C7 C8 C9 C10 -7.6(6) . . . . ?
C11 C8 C9 C10 114.5(5) . . . . ?
Cl1 C8 C9 C10 -128.3(4) . . . . ?
C8 C9 C10 C1 2.1(6) . . . . ?
C2 C1 C10 C9 -178.8(4) . . . . ?
C6 C1 C10 C9 1.6(6) . . . . ?
C12 O3 C11 O2 -3.0(7) . . . . ?
C12 O3 C11 C8 175.6(4) . . . . ?
C9 C8 C11 O2 97.7(6) . . . . ?
C7 C8 C11 O2 -136.2(5) . . . . ?
Cl1 C8 C11 O2 -19.2(6) . . . . ?
C9 C8 C11 O3 -80.9(4) . . . . ?
C7 C8 C11 O3 45.1(5) . . . . ?
Cl1 C8 C11 O3 162.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12C O2 0.98 2.61 3.578(7) 168.3 4_456
C9 H9 O1 0.95 2.50 3.198(5) 130.1 2_664

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_cd21437
_database_code_depnum_ccdc_archive 'CCDC 1048302'
_audit_update_record             
;
2015-02-07 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 Br Cl O3'
_chemical_formula_weight         315.54

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'
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   P2(1)2(1)2(1)

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

_cell_length_a                   7.4500(9)
_cell_length_b                   7.7960(9)
_cell_length_c                   21.193(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1230.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2331
_cell_measurement_theta_min      5.568
_cell_measurement_theta_max      45.917

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    3.548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.45967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  '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            7410
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2418
_reflns_number_gt                1968
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0494P)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     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2418
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_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 1.14929(7) 0.45076(8) 0.16199(3) 0.0953(3) Uani 1 1 d . . .
Cl1 Cl 0.67904(17) 1.13674(12) 0.03046(4) 0.0660(3) Uani 1 1 d . . .
O1 O 0.2886(4) 1.0313(4) 0.05586(15) 0.0759(9) Uani 1 1 d . . .
O2 O 0.5798(5) 1.2536(4) 0.15692(14) 0.0828(10) Uani 1 1 d . . .
O3 O 0.4551(4) 1.0110(3) 0.18889(10) 0.0520(7) Uani 1 1 d . . .
C1 C 0.4105(5) 0.9314(5) 0.06447(15) 0.0479(9) Uani 1 1 d . . .
C2 C 0.5903(5) 0.9998(4) 0.09073(15) 0.0424(8) Uani 1 1 d . . .
C3 C 0.7293(5) 0.8667(4) 0.10815(15) 0.0391(7) Uani 1 1 d . . .
C4 C 0.8865(5) 0.9119(5) 0.1374(2) 0.0594(10) Uani 1 1 d . . .
H4 H 0.9080 1.0266 0.1469 0.071 Uiso 1 1 calc R . .
C5 C 1.0127(5) 0.7906(5) 0.1530(2) 0.0649(11) Uani 1 1 d . . .
H5 H 1.1193 0.8229 0.1725 0.078 Uiso 1 1 calc R . .
C6 C 0.9800(5) 0.6210(5) 0.13957(17) 0.0538(9) Uani 1 1 d . . .
C7 C 0.8259(5) 0.5722(4) 0.10962(15) 0.0455(8) Uani 1 1 d . . .
H7 H 0.8071 0.4575 0.0996 0.055 Uiso 1 1 calc R . .
C8 C 0.6977(4) 0.6936(4) 0.09421(12) 0.0369(7) Uani 1 1 d . . .
C9 C 0.5303(5) 0.6421(4) 0.06409(14) 0.0465(8) Uani 1 1 d . . .
H9 H 0.5149 0.5269 0.0540 0.056 Uiso 1 1 calc R . .
C10 C 0.3984(5) 0.7505(5) 0.05031(15) 0.0499(9) Uani 1 1 d . . .
H10 H 0.2953 0.7087 0.0310 0.060 Uiso 1 1 calc R . .
C11 C 0.5443(5) 1.1081(4) 0.14834(15) 0.0440(8) Uani 1 1 d . . .
C12 C 0.3989(6) 1.0913(6) 0.24785(16) 0.0658(12) Uani 1 1 d . . .
H12A H 0.5027 1.1162 0.2731 0.099 Uiso 1 1 calc R . .
H12B H 0.3212 1.0147 0.2704 0.099 Uiso 1 1 calc R . .
H12C H 0.3359 1.1959 0.2388 0.099 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 1.892(4) . ?
Cl1 C2 1.791(3) . ?
O1 C1 1.210(5) . ?
O2 C11 1.178(4) . ?
O3 C11 1.324(4) . ?
O3 C12 1.459(4) . ?
C1 C10 1.445(5) . ?
C1 C2 1.545(5) . ?
C2 C3 1.512(5) . ?
C2 C11 1.524(5) . ?
C3 C4 1.372(5) . ?
C3 C8 1.401(5) . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.457(5) . ?
C9 C10 1.328(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C11 O3 C12 117.0(3) . . ?
O1 C1 C10 123.4(4) . . ?
O1 C1 C2 118.9(3) . . ?
C10 C1 C2 117.8(3) . . ?
C3 C2 C11 109.8(3) . . ?
C3 C2 C1 116.4(3) . . ?
C11 C2 C1 106.6(3) . . ?
C3 C2 Cl1 109.3(2) . . ?
C11 C2 Cl1 108.9(2) . . ?
C1 C2 Cl1 105.6(2) . . ?
C4 C3 C8 119.1(3) . . ?
C4 C3 C2 121.2(3) . . ?
C8 C3 C2 119.7(3) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 Br1 118.8(3) . . ?
C5 C6 Br1 120.3(3) . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 119.5(3) . . ?
C7 C8 C9 120.4(3) . . ?
C3 C8 C9 120.1(3) . . ?
C10 C9 C8 123.6(3) . . ?
C10 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
C9 C10 C1 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C1 C10 H10 119.0 . . ?
O2 C11 O3 124.2(3) . . ?
O2 C11 C2 127.3(3) . . ?
O3 C11 C2 108.4(3) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 C1 C2 C3 172.6(3) . . . . ?
C10 C1 C2 C3 -8.6(4) . . . . ?
O1 C1 C2 C11 49.8(4) . . . . ?
C10 C1 C2 C11 -131.4(3) . . . . ?
O1 C1 C2 Cl1 -65.9(4) . . . . ?
C10 C1 C2 Cl1 112.9(3) . . . . ?
C11 C2 C3 C4 -52.6(4) . . . . ?
C1 C2 C3 C4 -173.7(3) . . . . ?
Cl1 C2 C3 C4 66.8(4) . . . . ?
C11 C2 C3 C8 127.5(3) . . . . ?
C1 C2 C3 C8 6.3(4) . . . . ?
Cl1 C2 C3 C8 -113.1(3) . . . . ?
C8 C3 C4 C5 0.2(6) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C7 1.6(6) . . . . ?
C4 C5 C6 Br1 -178.8(3) . . . . ?
C5 C6 C7 C8 -2.1(5) . . . . ?
Br1 C6 C7 C8 178.3(2) . . . . ?
C6 C7 C8 C3 1.6(4) . . . . ?
C6 C7 C8 C9 -178.0(3) . . . . ?
C4 C3 C8 C7 -0.6(5) . . . . ?
C2 C3 C8 C7 179.3(3) . . . . ?
C4 C3 C8 C9 179.0(3) . . . . ?
C2 C3 C8 C9 -1.1(4) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C3 C8 C9 C10 -2.4(5) . . . . ?
C8 C9 C10 C1 -0.1(5) . . . . ?
O1 C1 C10 C9 -175.5(4) . . . . ?
C2 C1 C10 C9 5.7(5) . . . . ?
C12 O3 C11 O2 -0.3(6) . . . . ?
C12 O3 C11 C2 179.7(3) . . . . ?
C3 C2 C11 O2 110.7(5) . . . . ?
C1 C2 C11 O2 -122.5(5) . . . . ?
Cl1 C2 C11 O2 -9.0(5) . . . . ?
C3 C2 C11 O3 -69.4(4) . . . . ?
C1 C2 C11 O3 57.5(4) . . . . ?
Cl1 C2 C11 O3 171.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.063
