# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 1877937'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C5 H10 O4'
_chemical_formula_moiety         'C5 H10 O4'
_chemical_formula_weight         134.13
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.01554(7)
_cell_length_b                   7.52021(7)
_cell_length_c                   15.90107(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     599.755(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    16775
_cell_measurement_theta_min      5.5350
_cell_measurement_theta_max      73.4800

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             288

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.65035
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2031
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_number            20216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.564
_diffrn_reflns_theta_max         73.599
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.98
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.98
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_coverage         0.635
_reflns_number_total             1192
_reflns_number_gt                1167
_reflns_threshold_expression     'I > 2σ(I)'
_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.
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.2837P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1192
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.041


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8200(3) 0.1312(2) 0.37894(11) 0.0181(4) Uani 1 1 d . . . . .
H1A H 0.748657 0.063544 0.425734 0.022 Uiso 1 1 calc R U . . .
H1B H 0.751348 0.079491 0.327428 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7250(3) 0.3218(2) 0.38559(10) 0.0144(3) Uani 1 1 d . . . . .
H2 H 0.529677 0.323536 0.385969 0.017 Uiso 1 1 calc R U . . .
C3 C 0.8256(4) 0.4456(2) 0.31682(10) 0.0144(3) Uani 1 1 d . . . . .
H3 H 1.009967 0.415368 0.302234 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8171(4) 0.6268(2) 0.36082(10) 0.0180(4) Uani 1 1 d . . . . .
H4 H 0.930261 0.714603 0.332548 0.022 Uiso 1 1 calc R U . . .
C5 C 0.9263(4) 0.5754(2) 0.44594(10) 0.0207(4) Uani 1 1 d . . . . .
H5A H 1.119619 0.574095 0.445022 0.025 Uiso 1 1 calc R U . . .
H5B H 0.867444 0.658762 0.488623 0.025 Uiso 1 1 calc R U . . .
O1 O 0.8225(3) 0.39837(16) 0.46311(7) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.6608(3) 0.42988(17) 0.24496(7) 0.0209(3) Uani 1 1 d . . . . .
H2O H 0.729(3) 0.480(3) 0.2062(14) 0.031 Uiso 1 1 calc R U . . .
O3 O 0.5528(3) 0.68864(18) 0.37103(8) 0.0246(3) Uani 1 1 d . . . . .
H3O H 0.499(2) 0.730(4) 0.3267(15) 0.037 Uiso 1 1 calc R U . . .
O4 O 1.1023(3) 0.11722(18) 0.37920(8) 0.0206(3) Uani 1 1 d . . . . .
H4O H 1.1542(18) 0.119(3) 0.4255(16) 0.031 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O4 1.420(2) . ?
C1 C2 1.514(2) . ?
C2 O1 1.4455(19) . ?
C2 C3 1.522(2) . ?
C3 O2 1.4152(19) . ?
C3 C4 1.532(2) . ?
C4 O3 1.415(2) . ?
C4 C5 1.510(2) . ?
C5 O1 1.455(2) . ?

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
O4 C1 C2 112.57(14) . . ?
O1 C2 C1 109.29(13) . . ?
O1 C2 C3 104.89(13) . . ?
C1 C2 C3 115.12(14) . . ?
O2 C3 C2 109.59(13) . . ?
O2 C3 C4 115.26(13) . . ?
C2 C3 C4 101.92(13) . . ?
O3 C4 C5 108.72(15) . . ?
O3 C4 C3 111.78(14) . . ?
C5 C4 C3 99.88(13) . . ?
O1 C5 C4 105.82(13) . . ?
C2 O1 C5 108.99(11) . . ?

####################################################################### 
# 
# 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_13-Br
_database_code_depnum_ccdc_archive 'CCDC 1877938'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-03-14 downloaded from the CCDC.
;

_audit_creation_date             2018-11-08T23:07:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H13 Br O4'
_chemical_formula_moiety         'C12 H13 Br O4'
_chemical_formula_weight         301.13
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
_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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   22.3597(5)
_cell_length_b                   5.5295(2)
_cell_length_c                   9.5976(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.661(2)
_cell_angle_gamma                90
_cell_volume                     1186.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    7280
_cell_measurement_theta_min      3.8960
_cell_measurement_theta_max      73.0010

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             608

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.60607
_exptl_absorpt_correction_T_max  1.00000

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2031
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_number            8533
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.954
_diffrn_reflns_theta_max         73.524
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.93
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.849
_reflns_Friedel_coverage         0.687
_reflns_number_total             2218
_reflns_number_gt                2195
_reflns_threshold_expression     'I > 2σ(I)'
_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.
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.1887P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0604
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.045(19)
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.051


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br1 Br 0.28099(2) 0.57623(9) 0.89615(2) 0.03144(12) Uani 1 1 d . . . . .
O1 O 0.49825(9) 0.9370(4) 0.1681(2) 0.0241(4) Uani 1 1 d . . . . .
O2 O 0.53089(9) 1.4567(4) 0.1713(2) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.5174(16) 1.583(12) 0.172(3) 0.038 Uiso 1 1 calc R U . . .
O3 O 0.41679(9) 1.1471(4) 0.3701(2) 0.0222(5) Uani 1 1 d . . . . .
O4 O 0.37240(9) 0.8295(4) 0.2459(2) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.39199(13) 0.9186(6) 0.1142(3) 0.0260(6) Uani 1 1 d . . . . .
H1A H 0.359876 1.009614 0.070114 0.031 Uiso 1 1 calc R U . . .
H1B H 0.401559 0.783217 0.054137 0.031 Uiso 1 1 calc R U . . .
C2 C 0.44623(10) 1.0785(8) 0.1303(2) 0.0208(5) Uani 1 1 d . . . . .
H2A H 0.453491 1.163973 0.042694 0.025 Uiso 1 1 calc R U . . .
C3 C 0.44049(12) 1.2598(5) 0.2478(3) 0.0206(5) Uani 1 1 d . . . . .
H3 H 0.417747 1.403693 0.219831 0.025 Uiso 1 1 calc R U . . .
C4 C 0.50603(12) 1.3168(6) 0.2796(3) 0.0232(6) Uani 1 1 d . . . . .
H4 H 0.511773 1.391356 0.371437 0.028 Uiso 1 1 calc R U . . .
C5 C 0.53295(10) 1.0655(8) 0.2718(3) 0.0257(5) Uani 1 1 d . . . . .
H5A H 0.574577 1.074156 0.244826 0.031 Uiso 1 1 calc R U . . .
H5B H 0.530603 0.984999 0.361317 0.031 Uiso 1 1 calc R U . . .
C6 C 0.36274(11) 1.0195(5) 0.3408(3) 0.0228(6) Uani 1 1 d . . . . .
H6 H 0.3324 1.130792 0.30362 0.027 Uiso 1 1 calc R U . . .
C7 C 0.34208(11) 0.9122(6) 0.4757(3) 0.0212(6) Uani 1 1 d . . . . .
C8 C 0.36571(12) 0.6940(6) 0.5229(3) 0.0241(6) Uani 1 1 d . . . . .
H8 H 0.393534 0.612619 0.468949 0.029 Uiso 1 1 calc R U . . .
C9 C 0.34842(11) 0.5963(8) 0.6490(3) 0.0255(6) Uani 1 1 d . . . . .
H9 H 0.364377 0.450508 0.680286 0.031 Uiso 1 1 calc R U . . .
C10 C 0.30670(12) 0.7207(6) 0.7278(3) 0.0224(6) Uani 1 1 d . . . . .
C11 C 0.28261(13) 0.9386(6) 0.6843(3) 0.0257(6) Uani 1 1 d . . . . .
H11 H 0.254996 1.019935 0.738848 0.031 Uiso 1 1 calc R U . . .
C12 C 0.30057(12) 1.0340(6) 0.5570(3) 0.0237(6) Uani 1 1 d . . . . .
H12 H 0.284709 1.180242 0.526153 0.028 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.897(3) . ?
O1 C5 1.442(4) . ?
O1 C2 1.445(3) . ?
O2 C4 1.415(4) . ?
O3 C6 1.425(3) . ?
O3 C3 1.436(3) . ?
O4 C6 1.409(4) . ?
O4 C1 1.430(4) . ?
C1 C2 1.507(4) . ?
C2 C3 1.515(4) . ?
C3 C4 1.526(4) . ?
C4 C5 1.516(5) . ?
C6 C7 1.502(4) . ?
C7 C8 1.391(4) . ?
C7 C12 1.394(4) . ?
C8 C9 1.385(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.383(5) . ?
C11 C12 1.394(4) . ?

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
C5 O1 C2 109.4(2) . . ?
C6 O3 C3 111.9(2) . . ?
C6 O4 C1 111.4(2) . . ?
O4 C1 C2 111.4(2) . . ?
O1 C2 C1 110.7(3) . . ?
O1 C2 C3 104.26(19) . . ?
C1 C2 C3 112.9(2) . . ?
O3 C3 C2 110.9(2) . . ?
O3 C3 C4 106.8(2) . . ?
C2 C3 C4 101.3(2) . . ?
O2 C4 C5 107.7(2) . . ?
O2 C4 C3 110.5(2) . . ?
C5 C4 C3 100.5(2) . . ?
O1 C5 C4 106.0(2) . . ?
O4 C6 O3 111.2(2) . . ?
O4 C6 C7 108.3(2) . . ?
O3 C6 C7 107.1(2) . . ?
C8 C7 C12 119.3(3) . . ?
C8 C7 C6 120.3(3) . . ?
C12 C7 C6 120.4(3) . . ?
C9 C8 C7 121.0(3) . . ?
C8 C9 C10 118.6(3) . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 Br1 120.2(2) . . ?
C9 C10 Br1 117.8(3) . . ?
C10 C11 C12 118.6(3) . . ?
C7 C12 C11 120.6(3) . . ?

