# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463727'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Br O3'
_chemical_formula_weight         257.08

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   P2(1)/n

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                   15.7172(9)
_cell_length_b                   4.0206(2)
_cell_length_c                   17.5023(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.5950(10)
_cell_angle_gamma                90.00
_cell_volume                     1005.67(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5184
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.09

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    4.064
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.2176
_exptl_absorpt_correction_T_max  0.6867
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14425
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         29.99
_reflns_number_total             2928
_reflns_number_gt                2226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0542P)²+0.1504P] 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         2928
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.004
_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 0.735341(18) 0.39502(7) 1.153508(14) 0.06014(12) Uani 1 1 d . . .
O1 O 0.97141(12) 0.7957(5) 0.90283(12) 0.0618(5) Uani 1 1 d . . .
H1 H 1.0097 0.9100 0.9401 0.093 Uiso 1 1 calc R . .
O2 O 0.89728(12) 0.8307(4) 0.98638(10) 0.0556(4) Uani 1 1 d . . .
O3 O 0.57640(11) 0.7642(5) 0.78746(10) 0.0541(4) Uani 1 1 d . . .
C1 C 0.69836(14) 0.5505(5) 0.90733(13) 0.0375(4) Uani 1 1 d . . .
C2 C 0.60939(14) 0.6961(5) 0.87126(13) 0.0391(4) Uani 1 1 d . . .
C3 C 0.56104(15) 0.7649(6) 0.92007(15) 0.0467(5) Uani 1 1 d . . .
H3 H 0.5025 0.8656 0.8963 0.056 Uiso 1 1 calc R . .
C4 C 0.60079(16) 0.6823(6) 1.00456(15) 0.0482(5) Uani 1 1 d . . .
H4 H 0.5691 0.7297 1.0378 0.058 Uiso 1 1 calc R . .
C5 C 0.68675(15) 0.5309(5) 1.03943(13) 0.0410(4) Uani 1 1 d . . .
C6 C 0.73632(14) 0.4655(5) 0.99151(13) 0.0402(4) Uani 1 1 d . . .
H6 H 0.7948 0.3648 1.0159 0.048 Uiso 1 1 calc R . .
C7 C 0.74353(16) 0.4617(6) 0.85120(13) 0.0426(4) Uani 1 1 d . . .
H7 H 0.7056 0.3446 0.8032 0.051 Uiso 1 1 calc R . .
C8 C 0.82962(15) 0.5220(6) 0.85806(13) 0.0422(4) Uani 1 1 d . . .
H8 H 0.8459 0.4240 0.8179 0.051 Uiso 1 1 calc R . .
C9 C 0.90185(14) 0.7260(5) 0.92204(13) 0.0398(4) Uani 1 1 d . . .
C10 C 0.48216(17) 0.8768(7) 0.74521(19) 0.0640(7) Uani 1 1 d . . .
H10A H 0.4411 0.7235 0.7553 0.096 Uiso 1 1 calc R . .
H10B H 0.4656 0.8899 0.6859 0.096 Uiso 1 1 calc R . .
H10C H 0.4763 1.0927 0.7659 0.096 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 C5 1.897(2) . ?
O1 C9 1.301(2) . ?
O2 C9 1.232(3) . ?
O3 C2 1.365(2) . ?
O3 C10 1.426(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.401(3) . ?
C1 C7 1.476(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.372(3) . ?
C5 C6 1.387(3) . ?
C7 C8 1.330(3) . ?
C8 C9 1.469(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
C2 O3 C10 117.97(19) . . ?
C6 C1 C2 119.39(18) . . ?
C6 C1 C7 122.39(19) . . ?
C2 C1 C7 117.89(19) . . ?
O3 C2 C3 124.15(19) . . ?
O3 C2 C1 115.45(17) . . ?
C3 C2 C1 120.39(19) . . ?
C4 C3 C2 119.4(2) . . ?
C5 C4 C3 120.30(19) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 Br1 119.12(15) . . ?
C6 C5 Br1 120.03(17) . . ?
C1 C6 C5 119.7(2) . . ?
C8 C7 C1 130.5(2) . . ?
C7 C8 C9 127.22(19) . . ?
O2 C9 O1 122.5(2) . . ?
O2 C9 C8 124.55(18) . . ?
O1 C9 C8 112.90(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_collect_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1463728'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   3.9208(2)
_cell_length_b                   11.0581(7)
_cell_length_c                   12.1034(7)
_cell_angle_alpha                79.8570(10)
_cell_angle_beta                 86.8460(10)
_cell_angle_gamma                80.3430(10)
_cell_volume                     509.07(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3574
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.56

_exptl_crystal_description       Bar
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6499
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2193
_reflns_number_gt                1930
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0525P)²+0.1134P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_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
O1 O 0.2689(4) 0.87219(10) 1.07479(9) 0.0760(4) Uani 1 1 d . . . . .
H1 H 0.1628 0.9430 1.0732 0.114 Uiso 1 1 calc R U . . .
O2 O 0.0757(3) 0.90543(9) 0.90163(8) 0.0617(3) Uani 1 1 d . . . . .
O3 O 0.2103(3) 0.49236(8) 0.77843(8) 0.0465(3) Uani 1 1 d . . . . .
O4 O 0.2042(3) 0.76318(9) 0.42724(7) 0.0507(3) Uani 1 1 d . . . . .
C1 C 0.3774(3) 0.68775(10) 0.77065(10) 0.0356(3) Uani 1 1 d . . . . .
C2 C 0.2627(3) 0.60191(10) 0.71322(10) 0.0356(3) Uani 1 1 d . . . . .
C3 C 0.2082(3) 0.63025(11) 0.59908(10) 0.0388(3) Uani 1 1 d . . . . .
H3 H 0.1318 0.5731 0.5623 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2680(3) 0.74445(11) 0.53951(10) 0.0375(3) Uani 1 1 d . . . . .
C5 C 0.3847(3) 0.82974(11) 0.59344(10) 0.0400(3) Uani 1 1 d . . . . .
H5 H 0.4273 0.9058 0.5534 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4371(3) 0.80007(11) 0.70795(10) 0.0393(3) Uani 1 1 d . . . . .
H6 H 0.5151 0.8575 0.7440 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4643(3) 0.64918(11) 0.88900(10) 0.0421(3) Uani 1 1 d . . . . .
H7 H 0.5634 0.5660 0.9080 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4268(4) 0.71201(12) 0.97464(10) 0.0460(3) Uani 1 1 d . . . . .
H8 H 0.5304 0.6698 1.0408 0.055 Uiso 1 1 calc R U . . .
C9 C 0.2455(4) 0.83798(12) 0.97887(10) 0.0456(3) Uani 1 1 d . . . . .
C10 C 0.1040(4) 0.40060(12) 0.72427(13) 0.0517(4) Uani 1 1 d . . . . .
H10A H -0.1130 0.4338 0.6889 0.078 Uiso 1 1 calc R U . . .
H10B H 0.0779 0.3282 0.7789 0.078 Uiso 1 1 calc R U . . .
H10C H 0.2756 0.3781 0.6686 0.078 Uiso 1 1 calc R U . . .
C11 C 0.2883(4) 0.87343(14) 0.35943(12) 0.0563(4) Uani 1 1 d . . . . .
H11A H 0.1530 0.9448 0.3844 0.084 Uiso 1 1 calc R U . . .
H11B H 0.2388 0.8737 0.2826 0.084 Uiso 1 1 calc R U . . .
H11C H 0.5298 0.8762 0.3655 0.084 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
O1 C9 1.2952(15) . ?
O1 H1 0.8200 . ?
O2 C9 1.2368(16) . ?
O3 C2 1.3643(14) . ?
O3 C10 1.4281(15) . ?
O4 C4 1.3685(14) . ?
O4 C11 1.4217(17) . ?
C1 C6 1.3854(16) . ?
C1 C2 1.4130(16) . ?
C1 C7 1.4628(16) . ?
C2 C3 1.3821(17) . ?
C3 C4 1.3891(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3854(17) . ?
C5 C6 1.3853(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3348(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.4618(18) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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 H1 109.5 . . ?
C2 O3 C10 117.69(10) . . ?
C4 O4 C11 117.91(10) . . ?
C6 C1 C2 117.47(11) . . ?
C6 C1 C7 123.16(11) . . ?
C2 C1 C7 118.99(10) . . ?
O3 C2 C3 123.80(10) . . ?
O3 C2 C1 115.26(10) . . ?
C3 C2 C1 120.95(11) . . ?
C2 C3 C4 119.74(11) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O4 C4 C5 124.53(11) . . ?
O4 C4 C3 114.94(10) . . ?
C5 C4 C3 120.53(11) . . ?
C6 C5 C4 119.03(11) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 122.28(11) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C8 C7 C1 131.50(11) . . ?
C8 C7 H7 114.2 . . ?
C1 C7 H7 114.2 . . ?
C7 C8 C9 129.00(12) . . ?
C7 C8 H8 115.5 . . ?
C9 C8 H8 115.5 . . ?
O2 C9 O1 122.13(12) . . ?
O2 C9 C8 124.80(11) . . ?
O1 C9 C8 113.02(11) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463729'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 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 H12 O3'
_chemical_formula_weight         204.22

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   P2(1)/n

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                   4.0982(3)
_cell_length_b                   13.3942(9)
_cell_length_c                   20.0019(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.1250(10)
_cell_angle_gamma                90.00
_cell_volume                     1097.73(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3549
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.65

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8458
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1922
_reflns_number_gt                1625
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0992P)²+0.2685P] 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       0.053(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.0161(4) 0.08776(11) 0.05924(7) 0.0775(6) Uani 1 1 d . . .
O2 O -0.2303(5) -0.05979(12) 0.06401(8) 0.0845(6) Uani 1 1 d . . .
H2 H -0.1554 -0.0647 0.0264 0.127 Uiso 1 1 calc R . .
O3 O 0.1189(4) 0.18850(12) 0.30958(7) 0.0705(5) Uani 1 1 d . . .
C1 C -0.0523(5) 0.21035(14) 0.19746(9) 0.0536(5) Uani 1 1 d . . .
C2 C 0.1098(5) 0.24965(15) 0.25451(10) 0.0569(5) Uani 1 1 d . . .
C3 C 0.2494(5) 0.34460(17) 0.25304(12) 0.0691(6) Uani 1 1 d . . .
H3 H 0.3609 0.3691 0.2905 0.083 Uiso 1 1 calc R . .
C4 C 0.2221(7) 0.40218(19) 0.19608(14) 0.0820(8) Uani 1 1 d . . .
H4 H 0.3149 0.4655 0.1953 0.098 Uiso 1 1 calc R . .
C5 C 0.0574(7) 0.36623(18) 0.14006(13) 0.0830(8) Uani 1 1 d . . .
H5 H 0.0358 0.4058 0.1020 0.100 Uiso 1 1 calc R . .
C6 C -0.0759(6) 0.27059(16) 0.14068(11) 0.0684(6) Uani 1 1 d . . .
H6 H -0.1825 0.2464 0.1025 0.082 Uiso 1 1 calc R . .
C7 C -0.2123(5) 0.11280(15) 0.20258(9) 0.0552(5) Uani 1 1 d . . .
H7 H -0.2937 0.0996 0.2447 0.066 Uiso 1 1 calc R . .
C8 C -0.2643(5) 0.03870(15) 0.15829(9) 0.0557(5) Uani 1 1 d . . .
H8 H -0.3948 -0.0131 0.1733 0.067 Uiso 1 1 calc R . .
C9 C -0.1472(5) 0.02705(14) 0.08997(10) 0.0540(5) Uani 1 1 d . . .
C10 C 0.2518(7) 0.2281(2) 0.37123(12) 0.0835(8) Uani 1 1 d . . .
H10A H 0.1486 0.2912 0.3817 0.100 Uiso 1 1 calc R . .
H10B H 0.4847 0.2391 0.3675 0.100 Uiso 1 1 calc R . .
C11 C 0.1860(10) 0.1526(3) 0.42488(15) 0.1175(13) Uani 1 1 d . . .
H11 H 0.2540 0.0874 0.4173 0.141 Uiso 1 1 calc R . .
C12 C 0.0490(15) 0.1698(4) 0.4783(2) 0.1659(19) Uani 1 1 d . . .
H12A H -0.0228 0.2341 0.4878 0.199 Uiso 1 1 calc R . .
H12B H 0.0179 0.1186 0.5088 0.199 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
O1 C9 1.226(2) . ?
O2 C9 1.316(2) . ?
O3 C2 1.373(2) . ?
O3 C10 1.440(3) . ?
C1 C6 1.395(3) . ?
C1 C2 1.411(3) . ?
C1 C7 1.466(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.378(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.393(3) . ?
C7 C8 1.345(3) . ?
C8 C9 1.466(3) . ?
C10 C11 1.503(5) . ?
C11 C12 1.238(6) . ?

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
C2 O3 C10 118.12(19) . . ?
C6 C1 C2 117.81(19) . . ?
C6 C1 C7 123.25(18) . . ?
C2 C1 C7 118.69(18) . . ?
O3 C2 C3 123.80(19) . . ?
O3 C2 C1 115.55(18) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 120.1(2) . . ?
C3 C4 C5 120.3(2) . . ?
C4 C5 C6 119.9(2) . . ?
C5 C6 C1 121.2(2) . . ?
C8 C7 C1 132.62(17) . . ?
C7 C8 C9 129.96(18) . . ?
O1 C9 O2 121.88(18) . . ?
O1 C9 C8 126.08(18) . . ?
O2 C9 C8 112.02(17) . . ?
O3 C10 C11 107.1(2) . . ?
C12 C11 C10 125.5(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463730'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Br O3'
_chemical_formula_weight         257.08

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.770(2)
_cell_length_b                   4.7420(5)
_cell_length_c                   23.122(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.8600(10)
_cell_angle_gamma                90
_cell_volume                     2057.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296
_cell_measurement_reflns_used    2682
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.07

_exptl_crystal_description       Bar
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.973
_shelx_estimated_absorpt_T_min   0.382
_shelx_estimated_absorpt_T_max   0.890
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7936
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.762
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1922
_reflns_number_gt                1593
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0430P)²+8.0294P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_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 0.58966(3) 1.12775(14) 0.30242(2) 0.0776(2) Uani 1 1 d . . . . .
O1 O 0.56545(15) 0.2256(7) 0.01441(11) 0.0538(7) Uani 1 1 d . . . . .
O2 O 0.46675(15) 0.1543(7) 0.06462(12) 0.0551(7) Uani 1 1 d . . . . .
H3A H 0.4575 0.0496 0.0373 0.083 Uiso 1 1 calc R U . . .
O3 O 0.73047(15) 0.9132(8) 0.07453(13) 0.0642(9) Uani 1 1 d . . . . .
C1 C 0.63725(19) 0.8288(8) 0.13857(15) 0.0386(8) Uani 1 1 d . . . . .
C2 C 0.60451(19) 0.8809(8) 0.19111(16) 0.0422(8) Uani 1 1 d . . . . .
H2A H 0.5635 0.7820 0.2007 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6321(2) 1.0764(9) 0.22887(17) 0.0477(10) Uani 1 1 d . . . . .
C4 C 0.6919(2) 1.2276(9) 0.21537(19) 0.0525(10) Uani 1 1 d . . . . .
H4 H 0.7094 1.3631 0.2410 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7260(2) 1.1796(9) 0.16419(19) 0.0508(10) Uani 1 1 d . . . . .
H5 H 0.7667 1.2818 0.1553 0.061 Uiso 1 1 calc R U . . .
C6 C 0.69977(19) 0.9781(9) 0.12572(16) 0.0433(9) Uani 1 1 d . . . . .
C7 C 0.60926(19) 0.6222(8) 0.09743(15) 0.0405(8) Uani 1 1 d . . . . .
H7 H 0.6383 0.5787 0.0664 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5475(2) 0.4900(8) 0.09920(15) 0.0431(9) Uani 1 1 d . . . . .
H8 H 0.5162 0.5319 0.1288 0.052 Uiso 1 1 calc R U . . .
C9 C 0.52696(19) 0.2796(8) 0.05593(15) 0.0395(8) Uani 1 1 d . . . . .
C10 C 0.7971(3) 1.0427(16) 0.0614(2) 0.092(2) Uani 1 1 d . . . . .
H10A H 0.7904 1.2424 0.0571 0.138 Uiso 1 1 calc R U . . .
H10B H 0.8148 0.9658 0.0260 0.138 Uiso 1 1 calc R U . . .
H10C H 0.8307 1.0068 0.0922 0.138 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
Br1 C3 1.904(4) . ?
O1 C9 1.237(4) . ?
O2 C9 1.295(4) . ?
O3 C6 1.360(5) . ?
O3 C10 1.429(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.406(5) . ?
C1 C7 1.458(5) . ?
C2 C3 1.370(5) . ?
C3 C4 1.372(6) . ?
C4 C5 1.373(6) . ?
C5 C6 1.390(6) . ?
C7 C8 1.319(5) . ?
C8 C9 1.460(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
C6 O3 C10 118.1(4) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 C7 121.9(3) . . ?
C6 C1 C7 119.6(3) . . ?
C3 C2 C1 120.6(4) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 Br1 119.8(3) . . ?
C4 C3 Br1 119.4(3) . . ?
C3 C4 C5 120.2(4) . . ?
C4 C5 C6 120.0(4) . . ?
O3 C6 C5 124.2(4) . . ?
O3 C6 C1 115.8(3) . . ?
C5 C6 C1 120.0(4) . . ?
C8 C7 C1 127.4(3) . . ?
C7 C8 C9 121.8(3) . . ?
O1 C9 O2 123.1(3) . . ?
O1 C9 C8 121.5(3) . . ?
O2 C9 C8 115.4(3) . . ?

_refine_diff_density_max         1.025
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463731'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27.50 H28 O6'
_chemical_formula_weight         454.50

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.9527(5)
_cell_length_b                   10.3401(5)
_cell_length_c                   12.2625(6)
_cell_angle_alpha                82.4210(8)
_cell_angle_beta                 83.5482(9)
_cell_angle_gamma                82.2157(9)
_cell_volume                     1233.65(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5207
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      31.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6854
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10135
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.683
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4339
_reflns_number_gt                3690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.1141P)²+0.5344P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4339
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1925
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003

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
O1 O 0.43251(18) 0.14073(16) 0.04536(15) 0.0661(5) Uani 1 1 d . . . A 1
O2 O 0.3935(2) -0.06080(16) 0.11985(15) 0.0704(5) Uani 1 1 d . . . A 1
H2 H 0.4461 -0.0820 0.0670 0.106 Uiso 1 1 calc R U . A 1
O3 O 0.1764(3) 0.5126(2) 0.0926(2) 0.0991(7) Uani 1 1 d . . . A 1
O4 O 0.11827(19) 0.0772(2) 0.03345(12) 0.0700(5) Uani 1 1 d . . . A 1
O5 O -0.0195(2) -0.0365(2) 0.14985(13) 0.0739(6) Uani 1 1 d . . . A 1
H5 H -0.0534 -0.0421 0.0930 0.111 Uiso 1 1 calc R U . A 1
O6 O -0.0916(2) 0.42881(19) 0.30806(15) 0.0728(5) Uani 1 1 d . . . A 1
C1 C 0.2732(2) 0.3648(2) 0.23590(19) 0.0549(6) Uani 1 1 d . . . A 1
C2 C 0.2556(3) 0.4946(3) 0.1804(3) 0.0789(9) Uani 1 1 d . . . A 1
C3 C 0.3151(5) 0.5910(3) 0.2168(4) 0.1056(13) Uani 1 1 d . . . A 1
H3 H 0.3040 0.6762 0.1810 0.127 Uiso 1 1 calc R U . A 1
C4 C 0.3906(4) 0.5628(4) 0.3054(5) 0.1161(17) Uani 1 1 d . . . A 1
H4 H 0.4331 0.6288 0.3268 0.139 Uiso 1 1 calc R U . A 1
C5 C 0.4057(3) 0.4378(4) 0.3644(3) 0.0975(12) Uani 1 1 d . . . A 1
H5A H 0.4540 0.4207 0.4264 0.117 Uiso 1 1 calc R U . A 1
C6 C 0.3458(3) 0.3391(3) 0.3272(2) 0.0695(7) Uani 1 1 d . . . A 1
H6 H 0.3550 0.2546 0.3648 0.083 Uiso 1 1 calc R U . A 1
C7 C 0.2110(2) 0.2606(2) 0.19214(16) 0.0462(5) Uani 1 1 d . . . A 1
H7 H 0.2006 0.2873 0.1136 0.055 Uiso 1 1 calc R U . A 1
C8 C 0.2763(2) 0.1167(2) 0.20627(16) 0.0438(5) Uani 1 1 d . . . A 1
H8 H 0.3198 0.0995 0.2754 0.053 Uiso 1 1 calc R U . A 1
C9 C 0.3743(2) 0.0659(2) 0.11547(18) 0.0474(5) Uani 1 1 d . . . A 1
C10 C 0.1455(5) 0.6407(4) 0.0354(4) 0.1267(16) Uani 1 1 d . . . A 1
H10A H 0.1244 0.7031 0.0892 0.152 Uiso 1 1 calc R U . A 1
H10B H 0.0646 0.6420 -0.0022 0.152 Uiso 1 1 calc R U . A 1
C11 C 0.2524(8) 0.6831(6) -0.0439(5) 0.151(2) Uani 1 1 d . . . A 1
H11 H 0.2307 0.7715 -0.0690 0.181 Uiso 1 1 calc R U . A 1
C12 C 0.3505(10) 0.6467(13) -0.0847(8) 0.327(9) Uani 1 1 d . . . A 1
H12A H 0.3869 0.5595 -0.0685 0.393 Uiso 1 1 calc R U . A 1
H12B H 0.3980 0.7030 -0.1358 0.393 Uiso 1 1 calc R U . A 1
C21 C 0.0380(2) 0.2324(2) 0.36973(16) 0.0457(5) Uani 1 1 d . . . A 1
C22 C -0.0503(2) 0.3435(2) 0.39596(19) 0.0554(6) Uani 1 1 d . . . A 1
C23 C -0.0892(3) 0.3618(3) 0.5061(2) 0.0716(7) Uani 1 1 d . . . A 1
H23 H -0.1502 0.4343 0.5235 0.086 Uiso 1 1 calc R U . A 1
C24 C -0.0376(3) 0.2728(3) 0.5891(2) 0.0760(8) Uani 1 1 d . . . A 1
H24 H -0.0642 0.2857 0.6624 0.091 Uiso 1 1 calc R U . A 1
C25 C 0.0515(3) 0.1664(3) 0.56564(19) 0.0653(7) Uani 1 1 d . . . A 1
H25 H 0.0874 0.1077 0.6223 0.078 Uiso 1 1 calc R U . A 1
C26 C 0.0884(2) 0.1463(2) 0.45621(17) 0.0540(5) Uani 1 1 d . . . A 1
H26 H 0.1487 0.0728 0.4404 0.065 Uiso 1 1 calc R U . A 1
C27 C 0.0734(2) 0.2130(2) 0.24977(16) 0.0453(5) Uani 1 1 d . . . A 1
H27 H -0.0031 0.2468 0.2059 0.054 Uiso 1 1 calc R U . A 1
C28 C 0.1335(2) 0.0698(2) 0.22701(15) 0.0442(5) Uani 1 1 d . . . A 1
H28 H 0.1234 0.0041 0.2917 0.053 Uiso 1 1 calc R U . A 1
C29 C 0.0787(2) 0.0363(2) 0.12709(16) 0.0465(5) Uani 1 1 d . . . A 1
C30 C -0.1988(3) 0.5318(3) 0.3262(3) 0.0845(9) Uani 1 1 d . . . A 1
H30A H -0.1752 0.5854 0.3787 0.101 Uiso 1 1 calc R U . A 1
H30B H -0.2818 0.4951 0.3563 0.101 Uiso 1 1 calc R U . A 1
C31 C -0.2199(5) 0.6121(4) 0.2205(4) 0.1232(16) Uani 1 1 d . . . A 1
H31 H -0.2014 0.5629 0.1611 0.148 Uiso 1 1 calc R U . A 1
C32 C -0.2532(6) 0.7199(6) 0.1936(5) 0.167(2) Uani 1 1 d . . . A 1
H32A H -0.2745 0.7786 0.2460 0.200 Uiso 1 1 calc R U . A 1
H32B H -0.2594 0.7494 0.1191 0.200 Uiso 1 1 calc R U . A 1
C51 C 0.4326(16) 0.9466(14) 0.530(2) 0.193(11) Uani 0.5 1 d DG . P B -1
C52 C 0.4767(18) 1.0394(16) 0.5856(14) 0.152(8) Uani 0.5 1 d DG . P B -1
H52 H 0.4381 1.0521 0.6566 0.182 Uiso 0.5 1 calc R U P B -1
C53 C 0.5783(18) 1.1131(11) 0.535(2) 0.169(10) Uani 0.5 1 d G . P B -1
H53 H 0.6078 1.1752 0.5723 0.203 Uiso 0.5 1 calc R U P B -1
C54 C 0.6359(16) 1.0941(17) 0.429(2) 0.235(17) Uani 0.5 1 d G . P B -1
H54 H 0.7040 1.1434 0.3951 0.282 Uiso 0.5 1 calc R U P B -1
C55 C 0.592(2) 1.001(2) 0.3732(15) 0.209(13) Uani 0.5 1 d G . P B -1
H55 H 0.6304 0.9886 0.3021 0.251 Uiso 0.5 1 calc R U P B -1
C56 C 0.490(2) 0.9276(14) 0.4237(19) 0.233(16) Uani 0.5 1 d DG . P B -1
H56 H 0.4607 0.8656 0.3865 0.280 Uiso 0.5 1 calc R U P B -1
C57 C 0.331(3) 0.866(3) 0.585(3) 0.41(4) Uani 0.5 1 d D . P . .
H57A H 0.3710 0.8043 0.6423 0.616 Uiso 0.5 1 calc R U P B .
H57B H 0.2999 0.8183 0.5328 0.616 Uiso 0.5 1 calc R U P . .
H57C H 0.2557 0.9205 0.6178 0.616 Uiso 0.5 1 calc R U P . .


_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 1.228(3) . ?
O2 C9 1.293(3) . ?
O3 C2 1.384(4) . ?
O3 C10 1.426(4) . ?
O4 C29 1.211(2) . ?
O5 C29 1.297(3) . ?
O6 C22 1.364(3) . ?
O6 C30 1.423(3) . ?
C1 C6 1.378(4) . ?
C1 C2 1.420(4) . ?
C1 C7 1.497(3) . ?
C2 C3 1.371(5) . ?
C3 C4 1.368(7) . ?
C4 C5 1.393(7) . ?
C5 C6 1.398(4) . ?
C7 C8 1.536(3) . ?
C7 C27 1.579(3) . ?
C8 C9 1.496(3) . ?
C8 C28 1.547(3) . ?
C10 C11 1.432(7) . ?
C11 C12 1.089(10) . ?
C21 C26 1.385(3) . ?
C21 C22 1.398(3) . ?
C21 C27 1.507(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.374(4) . ?
C24 C25 1.357(4) . ?
C25 C26 1.386(3) . ?
C27 C28 1.568(3) . ?
C28 C29 1.494(3) . ?
C30 C31 1.464(5) . ?
C31 C32 1.136(6) . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C51 C57 1.452(18) . ?
C52 C53 1.3900 . ?
C53 C54 1.3900 . ?
C54 C55 1.3900 . ?
C55 C56 1.3900 . ?

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
C2 O3 C10 120.1(3) . . ?
C22 O6 C30 119.1(2) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C7 122.4(2) . . ?
C2 C1 C7 118.1(2) . . ?
C3 C2 O3 125.3(3) . . ?
C3 C2 C1 119.2(4) . . ?
O3 C2 C1 115.5(2) . . ?
C4 C3 C2 120.5(4) . . ?
C3 C4 C5 121.8(3) . . ?
C4 C5 C6 117.8(4) . . ?
C1 C6 C5 121.1(3) . . ?
C1 C7 C8 120.54(19) . . ?
C1 C7 C27 120.76(16) . . ?
C8 C7 C27 88.27(15) . . ?
C9 C8 C7 119.26(17) . . ?
C9 C8 C28 118.92(16) . . ?
C7 C8 C28 90.39(15) . . ?
O1 C9 O2 124.25(19) . . ?
O1 C9 C8 121.35(19) . . ?
O2 C9 C8 114.38(19) . . ?
O3 C10 C11 114.5(4) . . ?
C12 C11 C10 141.3(9) . . ?
C26 C21 C22 117.77(19) . . ?
C26 C21 C27 123.64(19) . . ?
C22 C21 C27 118.59(19) . . ?
O6 C22 C23 124.3(2) . . ?
O6 C22 C21 115.62(19) . . ?
C23 C22 C21 120.0(2) . . ?
C24 C23 C22 120.0(2) . . ?
C25 C24 C23 121.0(2) . . ?
C24 C25 C26 119.2(2) . . ?
C21 C26 C25 121.9(2) . . ?
C21 C27 C28 115.49(17) . . ?
C21 C27 C7 116.92(17) . . ?
C28 C27 C7 88.08(14) . . ?
C29 C28 C8 115.10(16) . . ?
C29 C28 C27 109.88(17) . . ?
C8 C28 C27 88.31(15) . . ?
O4 C29 O5 122.81(19) . . ?
O4 C29 C28 123.42(19) . . ?
O5 C29 C28 113.71(17) . . ?
O6 C30 C31 108.5(3) . . ?
C32 C31 C30 135.4(6) . . ?
C52 C51 C56 120.0 . . ?
C52 C51 C57 119.6(5) . . ?
C56 C51 C57 120.4(5) . . ?
C53 C52 C51 120.0 . . ?
C52 C53 C54 120.0 . . ?
C55 C54 C53 120.0 . . ?
C54 C55 C56 120.0 . . ?
C55 C56 C51 120.0 . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463732'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.7380(6)
_cell_length_b                   8.1099(6)
_cell_length_c                   10.0048(8)
_cell_angle_alpha                71.8220(10)
_cell_angle_beta                 84.9210(10)
_cell_angle_gamma                64.4150(10)
_cell_volume                     537.24(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5904
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1889
_reflns_number_gt                1521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0857P)²+0.1812P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.072(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1889
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1697
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
O1 O -0.3202(2) 0.9906(2) 0.09438(19) 0.0796(6) Uani 1 1 d . . . . .
O2 O -0.3077(3) 0.7996(3) -0.0285(2) 0.0839(6) Uani 1 1 d . . . . .
H2 H -0.4229 0.8706 -0.0404 0.126 Uiso 1 1 calc R U . . .
O3 O 0.2542(2) 0.8779(2) 0.3203(2) 0.0809(6) Uani 1 1 d . . . . .
C1 C 0.2808(3) 0.6574(3) 0.2052(2) 0.0602(6) Uani 1 1 d . . . . .
C2 C 0.3944(4) 0.4922(3) 0.1674(3) 0.0734(7) Uani 1 1 d . . . . .
H2A H 0.3385 0.4508 0.1138 0.088 Uiso 1 1 calc R U . . .
C3 C 0.5853(4) 0.3896(4) 0.2069(3) 0.0840(8) Uani 1 1 d . . . . .
H3 H 0.6579 0.2802 0.1802 0.101 Uiso 1 1 calc R U . . .
C4 C 0.6686(4) 0.4488(4) 0.2857(3) 0.0875(8) Uani 1 1 d . . . . .
H4 H 0.7985 0.3787 0.3128 0.105 Uiso 1 1 calc R U . . .
C5 C 0.5634(4) 0.6107(4) 0.3255(3) 0.0782(7) Uani 1 1 d . . . . .
H5 H 0.6219 0.6497 0.3791 0.094 Uiso 1 1 calc R U . . .
C6 C 0.3690(3) 0.7160(3) 0.2855(2) 0.0627(6) Uani 1 1 d . . . . .
C7 C 0.0772(3) 0.7679(3) 0.1625(2) 0.0627(6) Uani 1 1 d . . . . .
H7 H 0.0124 0.8769 0.1911 0.075 Uiso 1 1 calc R U . . .
C8 C -0.0249(4) 0.7295(3) 0.0876(3) 0.0704(7) Uani 1 1 d . . . . .
H8 H 0.0360 0.6214 0.0574 0.084 Uiso 1 1 calc R U . . .
C9 C -0.2290(4) 0.8492(3) 0.0501(2) 0.0664(6) Uani 1 1 d . . . . .
C10 C 0.3417(3) 0.9505(4) 0.3947(3) 0.0786(7) Uani 1 1 d . . . . .
H10A H 0.4420 0.9770 0.3405 0.094 Uiso 1 1 calc R U . . .
H10B H 0.3986 0.8562 0.4848 0.094 Uiso 1 1 calc R U . . .
C11 C 0.1956(5) 1.1241(7) 0.4160(7) 0.177(3) Uani 1 1 d . . . . .
H11 H 0.1080 1.1861 0.3388 0.212 Uiso 1 1 calc R U . . .
C12 C 0.1479(5) 1.2110(7) 0.4879(5) 0.1431(18) Uani 1 1 d . . . . .
H12A H 0.2187 1.1708 0.5716 0.172 Uiso 1 1 calc R U . . .
H12B H 0.0366 1.3251 0.4653 0.172 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
O1 C9 1.254(3) . ?
O2 C9 1.283(2) . ?
O3 C6 1.363(3) . ?
O3 C10 1.437(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.459(3) . ?
C2 C3 1.366(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.376(4) . ?
C5 C6 1.392(3) . ?
C7 C8 1.321(3) . ?
C8 C9 1.460(3) . ?
C10 C11 1.440(4) . ?
C11 C12 1.093(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
C6 O3 C10 118.05(18) . . ?
C2 C1 C6 117.7(2) . . ?
C2 C1 C7 122.0(2) . . ?
C6 C1 C7 120.3(2) . . ?
C3 C2 C1 121.8(2) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 C5 120.9(2) . . ?
C4 C5 C6 119.8(2) . . ?
O3 C6 C5 123.6(2) . . ?
O3 C6 C1 116.2(2) . . ?
C5 C6 C1 120.1(2) . . ?
C8 C7 C1 126.9(2) . . ?
C7 C8 C9 122.9(2) . . ?
O1 C9 O2 122.8(2) . . ?
O1 C9 C8 121.12(19) . . ?
O2 C9 C8 116.1(2) . . ?
O3 C10 C11 108.3(2) . . ?
C12 C11 C10 144.2(5) . . ?

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463733'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.5522(9)
_cell_length_b                   8.1546(10)
_cell_length_c                   8.9900(11)
_cell_angle_alpha                91.546(2)
_cell_angle_beta                 111.209(2)
_cell_angle_gamma                94.653(2)
_cell_volume                     513.50(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2050
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.02

_exptl_crystal_description       Bar
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4661
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2231
_reflns_number_gt                1636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0820P)²+0.1151P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2231
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O -0.04120(18) 0.12142(18) 0.14610(14) 0.0540(4) Uani 1 1 d . . . . .
H1 H -0.0778 0.0862 0.0525 0.081 Uiso 1 1 calc R U . . .
O2 O 0.19812(19) -0.03022(17) 0.16114(14) 0.0522(4) Uani 1 1 d . . . . .
O3 O -0.08111(18) 0.34673(18) 0.62970(14) 0.0540(4) Uani 1 1 d . . . . .
O4 O 0.40024(19) 0.33948(18) 1.14436(14) 0.0566(4) Uani 1 1 d . . . . .
C1 C 0.2019(2) 0.2269(2) 0.65326(18) 0.0367(4) Uani 1 1 d . . . . .
C2 C 0.0942(2) 0.3084(2) 0.72819(19) 0.0387(4) Uani 1 1 d . . . . .
C3 C 0.1664(3) 0.3437(2) 0.8918(2) 0.0436(4) Uani 1 1 d . . . . .
H3 H 0.0946 0.3969 0.9396 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3451(3) 0.3006(2) 0.98483(19) 0.0419(4) Uani 1 1 d . . . . .
C5 C 0.4551(3) 0.2217(2) 0.9147(2) 0.0470(4) Uani 1 1 d . . . . .
H5 H 0.5754 0.1930 0.9762 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3803(2) 0.1874(2) 0.7510(2) 0.0448(4) Uani 1 1 d . . . . .
H6 H 0.4537 0.1352 0.7040 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1240(2) 0.1871(2) 0.48109(19) 0.0392(4) Uani 1 1 d . . . . .
H7 H 0.0081 0.2268 0.4237 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2017(3) 0.0997(2) 0.3978(2) 0.0448(4) Uani 1 1 d . . . . .
H8 H 0.3185 0.0602 0.4524 0.054 Uiso 1 1 calc R U . . .
C9 C 0.1137(2) 0.0624(2) 0.2255(2) 0.0411(4) Uani 1 1 d . . . . .
C10 C -0.1912(3) 0.4330(3) 0.7005(2) 0.0571(5) Uani 1 1 d . . . . .
H10A H -0.2214 0.3652 0.7754 0.086 Uiso 1 1 calc R U . . .
H10B H -0.3071 0.4581 0.6185 0.086 Uiso 1 1 calc R U . . .
H10C H -0.1189 0.5334 0.7550 0.086 Uiso 1 1 calc R U . . .
C11 C 0.5828(3) 0.2977(3) 1.2476(2) 0.0629(6) Uani 1 1 d . . . . .
H11A H 0.5893 0.1813 1.2354 0.094 Uiso 1 1 calc R U . . .
H11B H 0.6005 0.3273 1.3565 0.094 Uiso 1 1 calc R U . . .
H11C H 0.6810 0.3564 1.2202 0.094 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
O1 C9 1.271(2) . ?
O2 C9 1.2780(19) . ?
O3 C2 1.367(2) . ?
O3 C10 1.429(2) . ?
O4 C4 1.3612(19) . ?
O4 C11 1.430(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.420(2) . ?
C1 C7 1.460(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.383(2) . ?
C7 C8 1.330(2) . ?
C8 C9 1.460(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
C2 O3 C10 117.54(13) . . ?
C4 O4 C11 118.31(14) . . ?
C6 C1 C2 116.95(14) . . ?
C6 C1 C7 122.67(14) . . ?
C2 C1 C7 120.37(15) . . ?
O3 C2 C3 123.50(14) . . ?
O3 C2 C1 116.05(14) . . ?
C3 C2 C1 120.46(15) . . ?
C2 C3 C4 120.52(15) . . ?
O4 C4 C3 115.35(15) . . ?
O4 C4 C5 124.24(16) . . ?
C3 C4 C5 120.41(15) . . ?
C6 C5 C4 118.18(16) . . ?
C5 C6 C1 123.47(15) . . ?
C8 C7 C1 126.66(16) . . ?
C7 C8 C9 123.64(16) . . ?
O1 C9 O2 122.81(15) . . ?
O1 C9 C8 119.76(14) . . ?
O2 C9 C8 117.43(15) . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1463734'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 O6'
_chemical_formula_weight         500.56

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.3783(4)
_cell_length_b                   9.3392(5)
_cell_length_c                   9.5107(5)
_cell_angle_alpha                75.7190(10)
_cell_angle_beta                 82.6330(10)
_cell_angle_gamma                69.6770(10)
_cell_volume                     675.55(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5751
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.28

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             266
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9178
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.212
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3260
_reflns_number_gt                2827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0766P)²+0.1044P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.179(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.30085(9) 1.06671(10) 0.55475(10) 0.0477(2) Uani 1 1 d . . . A 4
O2 O 0.40112(10) 0.93642(11) 0.37740(11) 0.0547(3) Uani 1 1 d . . . A 4
H2 H 0.4928 0.9340 0.4013 0.082 Uiso 1 1 calc R U . A 4
O3 O 0.20015(13) 0.58372(9) 0.42793(11) 0.0581(3) Uani 1 1 d . . . A 4
C1 C 0.17007(12) 0.73635(12) 0.59935(13) 0.0403(3) Uani 1 1 d . . . A 4
C2 C 0.24276(15) 0.59169(13) 0.55936(14) 0.0479(3) Uani 1 1 d . . . A 4
C3 C 0.3517(2) 0.46498(16) 0.65251(18) 0.0679(4) Uani 1 1 d . . . A 4
H3 H 0.4011 0.3695 0.6251 0.082 Uiso 1 1 calc R U . A 4
C4 C 0.3861(2) 0.48082(19) 0.78382(19) 0.0766(5) Uani 1 1 d . . . A 4
H4 H 0.4578 0.3955 0.8452 0.092 Uiso 1 1 calc R U . A 4
C5 C 0.3161(2) 0.6208(2) 0.82571(18) 0.0689(4) Uani 1 1 d . . . A 4
H5 H 0.3391 0.6309 0.9152 0.083 Uiso 1 1 calc R U . A 4
C6 C 0.20996(16) 0.74785(15) 0.73229(15) 0.0521(3) Uani 1 1 d . . . A 4
H6 H 0.1644 0.8434 0.7599 0.062 Uiso 1 1 calc R U . A 4
C7 C 0.04861(12) 0.87239(11) 0.50172(12) 0.0351(2) Uani 1 1 d . . . A 4
H7 H 0.0083 0.8349 0.4300 0.042 Uiso 1 1 calc R U . A 4
C8 C 0.10492(11) 1.01902(11) 0.42385(12) 0.0349(2) Uani 1 1 d . . . A 4
H8 H 0.0936 1.0428 0.3186 0.042 Uiso 1 1 calc R U . A 4
C9 C 0.27743(12) 1.01126(11) 0.45940(12) 0.0370(2) Uani 1 1 d . . . A 4
C10 C 0.2378(2) 0.42996(16) 0.40154(19) 0.0701(4) Uani 1 1 d . . . A 4
H10A H 0.1983 0.3647 0.4846 0.084 Uiso 1 1 calc R U . A 4
H10B H 0.3600 0.3823 0.3877 0.084 Uiso 1 1 calc R U . A 4
C11 C 0.1534(3) 0.4413(2) 0.2720(2) 0.0820(5) Uani 1 1 d . . . A 4
H11 H 0.0409 0.5069 0.2630 0.098 Uiso 1 1 calc R U . A 4
C12 C 0.2216(4) 0.3680(3) 0.1687(3) 0.1047(7) Uani 1 1 d . . . A 4
H12A H 0.3338 0.3011 0.1733 0.126 Uiso 1 1 calc R U . A 4
H12B H 0.1583 0.3821 0.0898 0.126 Uiso 1 1 calc R U . A 4
C21 C 0.1332(9) 0.9998(7) 0.9961(7) 0.115(3) Uani 0.5 1 d G . P B -1
C22 C 0.0768(11) 0.8851(6) 1.0893(6) 0.098(3) Uani 0.5 1 d G . P B -1
H22 H 0.1512 0.8050 1.1531 0.118 Uiso 0.5 1 calc R U P B -1
C23 C -0.0906(12) 0.8901(10) 1.0872(9) 0.153(5) Uani 0.5 1 d G . P B -1
H23 H -0.1283 0.8133 1.1495 0.183 Uiso 0.5 1 calc R U P B -1
C24 C -0.2017(10) 1.0098(13) 0.9918(11) 0.172(6) Uani 0.5 1 d G . P B -1
H24 H -0.3137 1.0131 0.9904 0.207 Uiso 0.5 1 calc R U P B -1
C25 C -0.1453(11) 1.1245(10) 0.8986(9) 0.145(6) Uani 0.5 1 d G . P B -1
H25 H -0.2197 1.2046 0.8348 0.174 Uiso 0.5 1 calc R U P B -1
C26 C 0.0221(11) 1.1195(7) 0.9007(7) 0.160(6) Uani 0.5 1 d G . P B -1
H26 H 0.0598 1.1963 0.8384 0.192 Uiso 0.5 1 calc R U P B -1
C27 C 0.2991(13) 1.0047(16) 0.9801(13) 0.168(5) Uani 0.5 1 d . . P B -1
H27A H 0.3405 0.9897 1.0740 0.252 Uiso 0.5 1 calc R U P B -1
H27B H 0.2999 1.1044 0.9222 0.252 Uiso 0.5 1 calc R U P B -1
H27C H 0.3711 0.9233 0.9332 0.252 Uiso 0.5 1 calc R U P B -1


_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 1.2154(14) . ?
O2 C9 1.3149(13) . ?
O3 C2 1.3690(17) . ?
O3 C10 1.4380(15) . ?
C1 C6 1.3864(18) . ?
C1 C2 1.4012(15) . ?
C1 C7 1.5081(14) . ?
C2 C3 1.3995(19) . ?
C3 C4 1.370(3) . ?
C4 C5 1.370(2) . ?
C5 C6 1.3919(18) . ?
C7 C8 1.5488(13) 2_576 ?
C7 C8 1.5828(13) . ?
C8 C9 1.4997(13) . ?
C8 C7 1.5488(13) 2_576 ?
C10 C11 1.461(3) . ?
C11 C12 1.295(3) . ?
C21 C22 1.3900 . ?
C21 C26 1.3900 . ?
C21 C27 1.394(13) . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
C25 C26 1.3900 . ?

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
C2 O3 C10 116.76(11) . . ?
C6 C1 C2 117.79(11) . . ?
C6 C1 C7 121.78(10) . . ?
C2 C1 C7 120.40(11) . . ?
O3 C2 C3 123.61(11) . . ?
O3 C2 C1 116.42(10) . . ?
C3 C2 C1 119.97(13) . . ?
C4 C3 C2 120.37(13) . . ?
C5 C4 C3 120.79(13) . . ?
C4 C5 C6 119.01(15) . . ?
C1 C6 C5 122.06(13) . . ?
C1 C7 C8 117.11(9) . 2_576 ?
C1 C7 C8 119.25(8) . . ?
C8 C7 C8 89.28(7) 2_576 . ?
C9 C8 C7 115.62(8) . 2_576 ?
C9 C8 C7 115.41(8) . . ?
C7 C8 C7 90.72(7) 2_576 . ?
O1 C9 O2 123.50(9) . . ?
O1 C9 C8 123.70(9) . . ?
O2 C9 C8 112.79(9) . . ?
O3 C10 C11 109.49(14) . . ?
C12 C11 C10 125.7(2) . . ?
C22 C21 C26 120.0 . . ?
C22 C21 C27 126.3(7) . . ?
C26 C21 C27 113.6(7) . . ?
C23 C22 C21 120.0 . . ?
C22 C23 C24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C25 C26 C21 120.0 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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 1463735'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Br2 O9'
_chemical_formula_weight         594.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.0513(5)
_cell_length_b                   10.3906(5)
_cell_length_c                   14.5614(7)
_cell_angle_alpha                108.1410(10)
_cell_angle_beta                 102.7940(10)
_cell_angle_gamma                94.1940(10)
_cell_volume                     1254.09(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6033
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.279
_shelx_estimated_absorpt_T_min   0.385
_shelx_estimated_absorpt_T_max   0.779
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4641
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS 2014/5 Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17137
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.523
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6049
_reflns_number_gt                4618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V8.34A (Bruker, 2015)'
_computing_data_reduction        'SAINT+  V8.34A (Bruker, 2015)'
_computing_structure_solution    'SHELXS/SHELXTL V6.14 (Bruker, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHELL v6.3.1 (Bruker, 2004)'
_computing_publication_material  'XCIF v2014/2 (Bruker, 2014)'
_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)+(0.0634P)²+1.2012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6049
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1317
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_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 0.84409(4) 1.06207(5) 1.18737(2) 0.06362(15) Uani 1 1 d . . . . .
Br2 Br 0.33725(7) 0.68970(5) 1.01976(4) 0.08609(19) Uani 1 1 d . . . . .
O1 O 0.7330(4) 0.9196(3) 0.61133(18) 0.0682(8) Uani 1 1 d . . . . .
O2 O 0.8129(3) 1.1340(2) 0.71099(17) 0.0521(6) Uani 1 1 d . . . . .
H2 H 0.8338 1.1425 0.6610 0.078 Uiso 1 1 calc R U . . .
O3 O 0.8606(3) 0.6165(2) 0.81223(17) 0.0539(6) Uani 1 1 d . . . . .
O4 O 0.3328(3) 0.8574(2) 0.61422(17) 0.0540(6) Uani 1 1 d . . . . .
O5 O 0.4222(3) 1.0787(2) 0.69337(19) 0.0549(6) Uani 1 1 d . . . . .
H5 H 0.3435 1.0883 0.6571 0.082 Uiso 1 1 calc R U . . .
O6 O 0.5399(3) 0.4991(2) 0.63896(19) 0.0605(7) Uani 1 1 d . . . . .
C1 C 0.8107(3) 0.8349(3) 0.8919(2) 0.0346(6) Uani 1 1 d . . . . .
C2 C 0.8585(3) 0.7121(3) 0.9000(2) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.8983(4) 0.6947(4) 0.9924(3) 0.0582(9) Uani 1 1 d . . . . .
H3 H 0.9288 0.6129 0.9968 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8930(4) 0.7977(4) 1.0778(3) 0.0578(9) Uani 1 1 d . . . . .
H4 H 0.9188 0.7854 1.1397 0.069 Uiso 1 1 calc R U . . .
C5 C 0.8494(3) 0.9180(4) 1.0704(2) 0.0434(7) Uani 1 1 d . . . . .
C6 C 0.8078(3) 0.9376(3) 0.9783(2) 0.0386(6) Uani 1 1 d . . . . .
H6 H 0.7779 1.0201 0.9750 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7556(3) 0.8409(3) 0.78829(19) 0.0324(5) Uani 1 1 d . . . . .
H7 H 0.8225 0.8023 0.7456 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7150(3) 0.9806(3) 0.77994(19) 0.0340(6) Uani 1 1 d . . . . .
H8 H 0.7536 1.0577 0.8427 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7546(3) 1.0071(3) 0.6918(2) 0.0378(6) Uani 1 1 d . . . . .
C10 C 0.8975(7) 0.4861(4) 0.8133(4) 0.0847(15) Uani 1 1 d . . . . .
H10A H 1.0006 0.4969 0.8528 0.127 Uiso 1 1 calc R U . . .
H10B H 0.8888 0.4274 0.7461 0.127 Uiso 1 1 calc R U . . .
H10C H 0.8281 0.4460 0.8416 0.127 Uiso 1 1 calc R U . . .
C11 C 0.5065(3) 0.6765(3) 0.7750(2) 0.0337(5) Uani 1 1 d . . . . .
C12 C 0.4900(4) 0.5350(3) 0.7248(2) 0.0450(7) Uani 1 1 d . . . . .
C13 C 0.4293(5) 0.4424(4) 0.7620(3) 0.0652(10) Uani 1 1 d . . . . .
H13 H 0.4202 0.3489 0.7283 0.078 Uiso 1 1 calc R U . . .
C14 C 0.3822(5) 0.4870(4) 0.8488(3) 0.0644(10) Uani 1 1 d . . . . .
H14 H 0.3410 0.4243 0.8736 0.077 Uiso 1 1 calc R U . . .
C15 C 0.3967(4) 0.6246(3) 0.8980(3) 0.0496(8) Uani 1 1 d . . . . .
C16 C 0.4585(3) 0.7192(3) 0.8620(2) 0.0382(6) Uani 1 1 d . . . . .
H16 H 0.4679 0.8124 0.8968 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5813(3) 0.7762(3) 0.73736(19) 0.0311(5) Uani 1 1 d . . . . .
H17 H 0.5676 0.7342 0.6651 0.037 Uiso 1 1 calc R U . . .
C18 C 0.5428(3) 0.9223(3) 0.75952(19) 0.0311(5) Uani 1 1 d . . . . .
H18 H 0.5127 0.9497 0.8227 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4227(3) 0.9480(3) 0.6807(2) 0.0352(6) Uani 1 1 d . . . . .
C20 C 0.5291(6) 0.3569(4) 0.5845(4) 0.0817(14) Uani 1 1 d . . . . .
H20A H 0.5878 0.3137 0.6266 0.122 Uiso 1 1 calc R U . . .
H20B H 0.5686 0.3467 0.5270 0.122 Uiso 1 1 calc R U . . .
H20C H 0.4238 0.3146 0.5631 0.122 Uiso 1 1 calc R U . . .
C21 C 1.0823(12) 0.5366(11) 0.5933(7) 0.192(6) Uani 1 1 d . . . . .
H21A H 1.1559 0.5313 0.6511 0.230 Uiso 1 1 calc R U . . .
H21B H 1.0626 0.6300 0.6040 0.230 Uiso 1 1 calc R U . . .
C22 C 0.8726(15) 0.5310(18) 0.5095(15) 0.301(11) Uani 1 1 d . . . . .
H22A H 0.9086 0.6288 0.5386 0.362 Uiso 1 1 calc R U . . .
H22B H 0.7633 0.5128 0.5025 0.362 Uiso 1 1 calc R U . . .
H31 H 0.199(5) 0.105(5) 0.512(4) 0.073(15) Uiso 1 1 d . . . . .
H32 H 0.108(6) 0.129(5) 0.560(4) 0.072(15) Uiso 1 1 d . . . . .
H33 H 0.921(6) 0.256(5) 0.563(4) 0.073(17) Uiso 1 1 d . . . . .
H34 H 0.831(7) 0.150(6) 0.508(4) 0.098(18) Uiso 1 1 d . . . . .
O11 O 0.1958(4) 0.1223(3) 0.5672(2) 0.0620(7) Uani 1 1 d . . . . .
O12 O 0.8950(3) 0.1920(3) 0.5619(2) 0.0487(6) Uani 1 1 d . . . . .
O13 O 0.9623(11) 0.4511(6) 0.5663(4) 0.198(3) Uani 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
Br1 C5 1.898(3) . ?
Br2 C15 1.903(3) . ?
O1 C9 1.203(4) . ?
O2 C9 1.304(4) . ?
O3 C2 1.358(4) . ?
O3 C10 1.423(4) . ?
O4 C19 1.207(4) . ?
O5 C19 1.313(3) . ?
O6 C12 1.374(4) . ?
O6 C20 1.428(4) . ?
C1 C6 1.380(4) . ?
C1 C2 1.408(4) . ?
C1 C7 1.502(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.378(6) . ?
C4 C5 1.367(5) . ?
C5 C6 1.392(4) . ?
C7 C8 1.557(4) . ?
C7 C17 1.583(4) . ?
C8 C9 1.503(4) . ?
C8 C18 1.559(4) . ?
C11 C16 1.383(4) . ?
C11 C12 1.403(4) . ?
C11 C17 1.500(4) . ?
C12 C13 1.380(5) . ?
C13 C14 1.376(6) . ?
C14 C15 1.367(5) . ?
C15 C16 1.387(4) . ?
C17 C18 1.533(4) . ?
C18 C19 1.500(4) . ?
C21 O13 1.255(9) . ?
C21 C22 1.599(17) 2_766 ?
C22 O13 1.503(12) . ?
C22 C21 1.599(17) 2_766 ?

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
C2 O3 C10 118.4(3) . . ?
C12 O6 C20 118.3(3) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 124.5(3) . . ?
C2 C1 C7 117.2(3) . . ?
O3 C2 C3 124.6(3) . . ?
O3 C2 C1 115.0(3) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 120.6(3) . . ?
C5 C4 C3 119.1(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 Br1 119.8(2) . . ?
C6 C5 Br1 118.8(3) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C7 C8 116.9(2) . . ?
C1 C7 C17 113.2(2) . . ?
C8 C7 C17 88.81(19) . . ?
C9 C8 C7 112.3(2) . . ?
C9 C8 C18 113.4(2) . . ?
C7 C8 C18 88.21(19) . . ?
O1 C9 O2 123.5(3) . . ?
O1 C9 C8 123.1(3) . . ?
O2 C9 C8 113.4(2) . . ?
C16 C11 C12 117.8(3) . . ?
C16 C11 C17 121.8(2) . . ?
C12 C11 C17 120.3(3) . . ?
O6 C12 C13 124.3(3) . . ?
O6 C12 C11 115.0(3) . . ?
C13 C12 C11 120.7(3) . . ?
C14 C13 C12 120.6(3) . . ?
C15 C14 C13 119.2(3) . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 Br2 120.3(3) . . ?
C16 C15 Br2 118.7(2) . . ?
C11 C16 C15 120.7(3) . . ?
C11 C17 C18 120.7(2) . . ?
C11 C17 C7 119.3(2) . . ?
C18 C17 C7 88.19(19) . . ?
C19 C18 C17 117.1(2) . . ?
C19 C18 C8 120.8(2) . . ?
C17 C18 C8 90.6(2) . . ?
O4 C19 O5 123.6(3) . . ?
O4 C19 C18 123.1(3) . . ?
O5 C19 C18 113.3(2) . . ?
O13 C21 C22 92.4(9) . 2_766 ?
O13 C22 C21 96.4(8) . 2_766 ?
C21 O13 C22 92.6(8) . . ?

_refine_diff_density_max         0.767
_refine_diff_density_min         -0.992
_refine_diff_density_rms         0.091

