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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AX0625
_database_code_depnum_ccdc_archive 'CCDC 1043341'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 Br O5'
_chemical_formula_weight         333.17

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   14.3578(16)
_cell_length_b                   11.7005(14)
_cell_length_c                   8.2619(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1387.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8498
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.66

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.145
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            21187
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         28.701
_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 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             3366
_reflns_number_gt                3054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.884

_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 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0200P)²] 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_abs_structure_details 
;
 Flack x determined using 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3366
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0483
_refine_ls_wR_factor_gt          0.0472
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
Br1 Br -0.15060(2) 0.26103(2) 0.33011(6) 0.02954(8) Uani 1 1 d . . . . .
C1 C 0.10776(16) 0.2888(2) 0.9309(3) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.14732(14) 0.17106(19) 0.9844(3) 0.0206(5) Uani 1 1 d . . . . .
H2 H 0.1757 0.1776 1.0945 0.025 Uiso 1 1 calc R U . . .
C3 C 0.19040(16) 0.3722(2) 0.9084(3) 0.0214(5) Uani 1 1 d . . . . .
C4 C 0.31511(17) 0.4643(2) 1.0391(3) 0.0297(5) Uani 1 1 d . . . . .
H4A H 0.3636 0.4369 0.9652 0.044 Uiso 1 1 calc R U . . .
H4B H 0.3415 0.4736 1.1477 0.044 Uiso 1 1 calc R U . . .
H4C H 0.2914 0.5380 1.0007 0.044 Uiso 1 1 calc R U . . .
C5 C 0.02582(17) 0.44018(19) 1.0667(3) 0.0274(5) Uani 1 1 d . . . . .
H5A H 0.0798 0.4898 1.0851 0.041 Uiso 1 1 calc R U . . .
H5B H -0.0203 0.4527 1.1523 0.041 Uiso 1 1 calc R U . . .
H5C H -0.0020 0.4581 0.9613 0.041 Uiso 1 1 calc R U . . .
C6 C 0.05798(18) 0.0389(2) 1.1406(3) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.1168 0.0117 1.1870 0.047 Uiso 1 1 calc R U . . .
H6B H 0.0151 -0.0257 1.1278 0.047 Uiso 1 1 calc R U . . .
H6C H 0.0301 0.0958 1.2129 0.047 Uiso 1 1 calc R U . . .
C7 C 0.26852(16) 0.0437(2) 0.9230(3) 0.0281(5) Uani 1 1 d . . . . .
H7A H 0.3003 0.0613 1.0250 0.042 Uiso 1 1 calc R U . . .
H7B H 0.3148 0.0247 0.8401 0.042 Uiso 1 1 calc R U . . .
H7C H 0.2266 -0.0215 0.9389 0.042 Uiso 1 1 calc R U . . .
C8 C 0.04759(16) 0.27881(18) 0.7796(3) 0.0184(5) Uani 1 1 d . . . . .
C9 C 0.08441(17) 0.2757(2) 0.6234(3) 0.0219(5) Uani 1 1 d . . . . .
H9 H 0.1500 0.2777 0.6088 0.026 Uiso 1 1 calc R U . . .
C10 C 0.02620(17) 0.26961(18) 0.4881(3) 0.0211(5) Uani 1 1 d . . . . .
H10 H 0.0517 0.2689 0.3820 0.025 Uiso 1 1 calc R U . . .
C11 C -0.06921(18) 0.26459(17) 0.5111(3) 0.0203(5) Uani 1 1 d . . . . .
C12 C -0.10747(17) 0.26306(18) 0.6650(3) 0.0226(5) Uani 1 1 d . . . . .
H12 H -0.1730 0.2575 0.6792 0.027 Uiso 1 1 calc R U . . .
C13 C -0.04880(16) 0.26975(17) 0.7980(3) 0.0212(5) Uani 1 1 d . . . . .
H13 H -0.0747 0.2681 0.9037 0.025 Uiso 1 1 calc R U . . .
O1 O 0.20758(12) 0.42494(15) 0.7874(2) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.23910(11) 0.38167(14) 1.04470(19) 0.0266(4) Uani 1 1 d . . . . .
O3 O 0.05496(11) 0.32331(14) 1.06847(18) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.07540(11) 0.08946(13) 0.9864(2) 0.0254(4) Uani 1 1 d . . . . .
O5 O 0.21551(10) 0.14138(14) 0.87167(18) 0.0248(4) 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 C11 1.898(2) . ?
C1 O3 1.424(3) . ?
C1 C8 1.524(3) . ?
C1 C3 1.547(3) . ?
C1 C2 1.555(3) . ?
C2 O5 1.395(3) . ?
C2 O4 1.406(3) . ?
C2 H2 1.0000 . ?
C3 O1 1.200(3) . ?
C3 O2 1.330(3) . ?
C4 O2 1.459(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O3 1.430(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O4 1.427(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 O5 1.437(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.395(3) . ?
C8 C13 1.396(3) . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
O3 C1 C8 111.99(17) . . ?
O3 C1 C3 109.02(19) . . ?
C8 C1 C3 112.62(19) . . ?
O3 C1 C2 102.63(18) . . ?
C8 C1 C2 111.83(19) . . ?
C3 C1 C2 108.23(18) . . ?
O5 C2 O4 110.74(18) . . ?
O5 C2 C1 106.71(17) . . ?
O4 C2 C1 109.69(18) . . ?
O5 C2 H2 109.9 . . ?
O4 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
O1 C3 O2 123.7(2) . . ?
O1 C3 C1 125.6(2) . . ?
O2 C3 C1 110.71(19) . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 H6A 109.5 . . ?
O4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C1 123.1(2) . . ?
C13 C8 C1 118.60(19) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 Br1 120.13(19) . . ?
C12 C11 Br1 118.59(19) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C3 O2 C4 114.93(17) . . ?
C1 O3 C5 114.71(18) . . ?
C2 O4 C6 114.89(17) . . ?
C2 O5 C7 111.89(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 O5 -167.85(17) . . . . ?
C8 C1 C2 O5 71.9(2) . . . . ?
C3 C1 C2 O5 -52.7(2) . . . . ?
O3 C1 C2 O4 72.1(2) . . . . ?
C8 C1 C2 O4 -48.1(2) . . . . ?
C3 C1 C2 O4 -172.69(18) . . . . ?
O3 C1 C3 O1 -124.8(3) . . . . ?
C8 C1 C3 O1 0.1(3) . . . . ?
C2 C1 C3 O1 124.3(3) . . . . ?
O3 C1 C3 O2 52.8(2) . . . . ?
C8 C1 C3 O2 177.74(18) . . . . ?
C2 C1 C3 O2 -58.1(2) . . . . ?
O3 C1 C8 C9 163.0(2) . . . . ?
C3 C1 C8 C9 39.7(3) . . . . ?
C2 C1 C8 C9 -82.5(3) . . . . ?
O3 C1 C8 C13 -18.5(3) . . . . ?
C3 C1 C8 C13 -141.8(2) . . . . ?
C2 C1 C8 C13 96.1(2) . . . . ?
C13 C8 C9 C10 3.3(3) . . . . ?
C1 C8 C9 C10 -178.2(2) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C9 C10 C11 Br1 178.05(17) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
Br1 C11 C12 C13 -177.72(15) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C9 C8 C13 C12 -2.9(3) . . . . ?
C1 C8 C13 C12 178.48(19) . . . . ?
O1 C3 O2 C4 1.5(3) . . . . ?
C1 C3 O2 C4 -176.13(19) . . . . ?
C8 C1 O3 C5 -72.2(2) . . . . ?
C3 C1 O3 C5 53.1(2) . . . . ?
C2 C1 O3 C5 167.69(18) . . . . ?
O5 C2 O4 C6 123.4(2) . . . . ?
C1 C2 O4 C6 -119.1(2) . . . . ?
O4 C2 O5 C7 -70.7(2) . . . . ?
C1 C2 O5 C7 169.95(19) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AX0635
_database_code_depnum_ccdc_archive 'CCDC 1043342'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 O7'
_chemical_formula_weight         374.37

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.7096(3)
_cell_length_b                   7.1009(2)
_cell_length_c                   26.6401(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.031(1)
_cell_angle_gamma                90
_cell_volume                     1808.67(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.58

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            35963
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         28.000
_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             4368
_reflns_number_gt                3616
_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 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0494P)²+1.2497P] 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         4368
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 1.61585(16) -0.1108(2) 0.23226(6) 0.0268(3) Uani 1 1 d . . . . .
H1A H 1.6903 -0.1437 0.2127 0.032 Uiso 1 1 calc R U . . .
H1B H 1.6151 -0.2073 0.2590 0.032 Uiso 1 1 calc R U . . .
C2 C 1.43071(15) 0.0708(2) 0.20432(6) 0.0211(3) Uani 1 1 d . . . . .
C3 C 1.30546(14) 0.1418(2) 0.18020(6) 0.0210(3) Uani 1 1 d . . . . .
H3 H 1.2425 0.0676 0.1570 0.025 Uiso 1 1 calc R U . . .
C4 C 1.27360(14) 0.3296(2) 0.19113(5) 0.0193(3) Uani 1 1 d . . . . .
C5 C 1.36907(15) 0.4340(2) 0.22533(6) 0.0228(3) Uani 1 1 d . . . . .
H5 H 1.3466 0.5602 0.2326 0.027 Uiso 1 1 calc R U . . .
C6 C 1.49694(15) 0.3589(2) 0.24932(6) 0.0240(3) Uani 1 1 d . . . . .
H6 H 1.5614 0.4312 0.2725 0.029 Uiso 1 1 calc R U . . .
C7 C 1.52481(14) 0.1764(2) 0.23785(6) 0.0214(3) Uani 1 1 d . . . . .
C8 C 1.13881(15) 0.4114(2) 0.16554(5) 0.0197(3) Uani 1 1 d . . . . .
C9 C 1.12770(15) 0.6006(2) 0.15132(6) 0.0229(3) Uani 1 1 d . . . . .
H9 H 1.2068 0.6807 0.1595 0.028 Uiso 1 1 calc R U . . .
C10 C 1.00244(15) 0.6739(2) 0.12532(6) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.9973 0.8028 0.1157 0.027 Uiso 1 1 calc R U . . .
C11 C 0.88436(15) 0.5600(2) 0.11330(5) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.89482(15) 0.3716(2) 0.12771(6) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.8155 0.2918 0.1197 0.026 Uiso 1 1 calc R U . . .
C13 C 1.01980(15) 0.2990(2) 0.15359(6) 0.0214(3) Uani 1 1 d . . . . .
H13 H 1.0245 0.1702 0.1634 0.026 Uiso 1 1 calc R U . . .
C14 C 0.74945(15) 0.6280(2) 0.08031(5) 0.0204(3) Uani 1 1 d . . . . .
C15 C 0.70795(15) 0.8301(2) 0.09281(5) 0.0211(3) Uani 1 1 d . . . . .
C16 C 0.53489(19) 1.0616(2) 0.06944(7) 0.0340(4) Uani 1 1 d . . . . .
H16A H 0.5141 1.0646 0.1041 0.051 Uiso 1 1 calc R U . . .
H16B H 0.4486 1.0824 0.0449 0.051 Uiso 1 1 calc R U . . .
H16C H 0.6025 1.1607 0.0657 0.051 Uiso 1 1 calc R U . . .
C17 C 0.58297(17) 0.5176(2) 0.13068(6) 0.0280(3) Uani 1 1 d . . . . .
H17A H 0.6612 0.5033 0.1591 0.042 Uiso 1 1 calc R U . . .
H17B H 0.5147 0.4169 0.1321 0.042 Uiso 1 1 calc R U . . .
H17C H 0.5381 0.6401 0.1332 0.042 Uiso 1 1 calc R U . . .
C18 C 0.76256(16) 0.6194(2) 0.02340(6) 0.0251(3) Uani 1 1 d . . . . .
H18 H 0.6692 0.6413 0.0016 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7310(2) 0.3405(3) -0.02733(8) 0.0467(5) Uani 1 1 d . . . . .
H19A H 0.6359 0.3264 -0.0202 0.070 Uiso 1 1 calc R U . . .
H19B H 0.7723 0.2157 -0.0300 0.070 Uiso 1 1 calc R U . . .
H19C H 0.7279 0.4086 -0.0595 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8794(2) 0.7756(3) -0.03538(7) 0.0387(4) Uani 1 1 d . . . . .
H20A H 0.9260 0.6605 -0.0439 0.058 Uiso 1 1 calc R U . . .
H20B H 0.9391 0.8846 -0.0387 0.058 Uiso 1 1 calc R U . . .
H20C H 0.7900 0.7898 -0.0586 0.058 Uiso 1 1 calc R U . . .
O1 O 1.48335(12) -0.10620(16) 0.19915(5) 0.0338(3) Uani 1 1 d . . . . .
O2 O 1.64243(11) 0.07074(16) 0.25502(5) 0.0314(3) Uani 1 1 d . . . . .
O3 O 0.76347(12) 0.92628(15) 0.12731(4) 0.0283(3) Uani 1 1 d . . . . .
O4 O 0.59295(11) 0.88040(15) 0.06005(4) 0.0271(3) Uani 1 1 d . . . . .
O5 O 0.63386(11) 0.50696(15) 0.08350(4) 0.0229(2) Uani 1 1 d . . . . .
O6 O 0.81373(12) 0.44306(17) 0.01290(4) 0.0318(3) Uani 1 1 d . . . . .
O7 O 0.85477(13) 0.76383(17) 0.01595(4) 0.0327(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
C1 O1 1.4279(18) . ?
C1 O2 1.4290(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.369(2) . ?
C2 O1 1.3729(17) . ?
C2 C7 1.382(2) . ?
C3 C4 1.410(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(2) . ?
C4 C8 1.4848(19) . ?
C5 C6 1.399(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(2) . ?
C6 H6 0.9500 . ?
C7 O2 1.3764(17) . ?
C8 C13 1.395(2) . ?
C8 C9 1.395(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 C14 1.5231(19) . ?
C12 C13 1.3865(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O5 1.4276(17) . ?
C14 C15 1.543(2) . ?
C14 C18 1.544(2) . ?
C15 O3 1.1956(18) . ?
C15 O4 1.3403(17) . ?
C16 O4 1.4439(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O5 1.4304(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O6 1.3934(18) . ?
C18 O7 1.398(2) . ?
C18 H18 1.0000 . ?
C19 O6 1.423(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O7 1.431(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 108.54(12) . . ?
O1 C1 H1A 110.0 . . ?
O2 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C3 C2 O1 127.30(13) . . ?
C3 C2 C7 122.46(13) . . ?
O1 C2 C7 110.23(13) . . ?
C2 C3 C4 117.39(13) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 119.53(13) . . ?
C5 C4 C8 121.61(13) . . ?
C3 C4 C8 118.86(13) . . ?
C4 C5 C6 122.12(14) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 116.93(13) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 O2 128.80(13) . . ?
C6 C7 C2 121.57(13) . . ?
O2 C7 C2 109.62(13) . . ?
C13 C8 C9 117.87(13) . . ?
C13 C8 C4 120.65(13) . . ?
C9 C8 C4 121.46(13) . . ?
C10 C9 C8 120.98(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.67(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.50(13) . . ?
C12 C11 C14 118.55(13) . . ?
C10 C11 C14 122.63(13) . . ?
C13 C12 C11 120.69(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 121.28(13) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O5 C14 C11 112.41(12) . . ?
O5 C14 C15 108.03(11) . . ?
C11 C14 C15 113.62(12) . . ?
O5 C14 C18 103.58(11) . . ?
C11 C14 C18 110.14(12) . . ?
C15 C14 C18 108.52(12) . . ?
O3 C15 O4 124.13(13) . . ?
O3 C15 C14 126.71(13) . . ?
O4 C15 C14 109.08(12) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 O7 111.78(12) . . ?
O6 C18 C14 109.01(12) . . ?
O7 C18 C14 105.96(12) . . ?
O6 C18 H18 110.0 . . ?
O7 C18 H18 110.0 . . ?
C14 C18 H18 110.0 . . ?
O6 C19 H19A 109.5 . . ?
O6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 O1 C1 105.68(12) . . ?
C7 O2 C1 105.83(11) . . ?
C15 O4 C16 115.53(12) . . ?
C14 O5 C17 114.57(11) . . ?
C18 O6 C19 115.93(13) . . ?
C18 O7 C20 113.35(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.42(14) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C8 179.83(13) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C8 C4 C5 C6 -179.42(14) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C5 C6 C7 O2 178.53(15) . . . . ?
C5 C6 C7 C2 -0.3(2) . . . . ?
C3 C2 C7 C6 0.7(2) . . . . ?
O1 C2 C7 C6 179.71(14) . . . . ?
C3 C2 C7 O2 -178.30(14) . . . . ?
O1 C2 C7 O2 0.66(18) . . . . ?
C5 C4 C8 C13 -147.25(15) . . . . ?
C3 C4 C8 C13 33.1(2) . . . . ?
C5 C4 C8 C9 34.7(2) . . . . ?
C3 C4 C8 C9 -144.96(15) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
C4 C8 C9 C10 177.09(13) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 C14 -173.62(13) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C14 C11 C12 C13 173.86(13) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C9 C8 C13 C12 1.0(2) . . . . ?
C4 C8 C13 C12 -177.14(13) . . . . ?
C12 C11 C14 O5 21.18(18) . . . . ?
C10 C11 C14 O5 -165.45(13) . . . . ?
C12 C11 C14 C15 144.26(13) . . . . ?
C10 C11 C14 C15 -42.37(19) . . . . ?
C12 C11 C14 C18 -93.75(16) . . . . ?
C10 C11 C14 C18 79.61(17) . . . . ?
O5 C14 C15 O3 118.78(16) . . . . ?
C11 C14 C15 O3 -6.7(2) . . . . ?
C18 C14 C15 O3 -129.55(16) . . . . ?
O5 C14 C15 O4 -57.99(15) . . . . ?
C11 C14 C15 O4 176.57(12) . . . . ?
C18 C14 C15 O4 53.69(15) . . . . ?
O5 C14 C18 O6 -71.36(14) . . . . ?
C11 C14 C18 O6 49.06(16) . . . . ?
C15 C14 C18 O6 174.02(12) . . . . ?
O5 C14 C18 O7 168.20(11) . . . . ?
C11 C14 C18 O7 -71.39(15) . . . . ?
C15 C14 C18 O7 53.57(15) . . . . ?
C3 C2 O1 C1 -179.76(15) . . . . ?
C7 C2 O1 C1 1.34(17) . . . . ?
O2 C1 O1 C2 -2.78(17) . . . . ?
C6 C7 O2 C1 178.68(16) . . . . ?
C2 C7 O2 C1 -2.36(17) . . . . ?
O1 C1 O2 C7 3.17(17) . . . . ?
O3 C15 O4 C16 -1.5(2) . . . . ?
C14 C15 O4 C16 175.40(13) . . . . ?
C11 C14 O5 C17 72.37(15) . . . . ?
C15 C14 O5 C17 -53.79(15) . . . . ?
C18 C14 O5 C17 -168.77(12) . . . . ?
O7 C18 O6 C19 -118.45(17) . . . . ?
C14 C18 O6 C19 124.76(16) . . . . ?
O6 C18 O7 C20 61.15(17) . . . . ?
C14 C18 O7 C20 179.78(12) . . . . ?

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AX0724
_database_code_depnum_ccdc_archive 'CCDC 1043343'
_audit_update_record             
;
2015-01-13 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 Br O5'
_chemical_formula_weight         319.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.7047(6)
_cell_length_b                   8.5755(4)
_cell_length_c                   13.6576(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.5461(7)
_cell_angle_gamma                90
_cell_volume                     1342.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9008
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      28.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.224
_exptl_absorpt_coefficient_mu    3.072
_shelx_estimated_absorpt_T_min   0.332
_shelx_estimated_absorpt_T_max   0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_T_max  0.55
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            20230
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.777
_diffrn_reflns_theta_max         27.995
_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             3240
_reflns_number_gt                2896
_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 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0343P)²+1.8909P] 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         3240
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0816
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Br1 Br 0.25990(2) 0.14079(3) 0.20958(2) 0.03836(10) Uani 1 1 d . . . . .
C1 C 0.16844(18) 0.8125(3) 0.44092(18) 0.0241(4) Uani 1 1 d . . . . .
H1 H 0.1735 0.9019 0.4898 0.029 Uiso 1 1 calc R U . . .
C2 C 0.28908(18) 0.7324(2) 0.47990(16) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.28258(17) 0.5906(2) 0.41060(16) 0.0208(4) Uani 1 1 d . . . . .
C4 C 0.28567(18) 0.6022(3) 0.30967(17) 0.0233(4) Uani 1 1 d . . . . .
H4 H 0.2930 0.7016 0.2825 0.028 Uiso 1 1 calc R U . . .
C5 C 0.27806(19) 0.4692(3) 0.24906(18) 0.0264(4) Uani 1 1 d . . . . .
H5B H 0.2810 0.4770 0.1809 0.032 Uiso 1 1 calc R U . . .
C6 C 0.26611(19) 0.3250(3) 0.28873(18) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.2599(2) 0.3110(3) 0.38659(19) 0.0284(5) Uani 1 1 d . . . . .
H7 H 0.2501 0.2117 0.4124 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2681(2) 0.4445(3) 0.44681(17) 0.0266(4) Uani 1 1 d . . . . .
H8 H 0.2636 0.4358 0.5143 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0463(2) 0.7268(4) 0.5226(2) 0.0402(6) Uani 1 1 d . . . . .
H9A H 0.1118 0.7097 0.5937 0.060 Uiso 1 1 calc R U . . .
H9B H -0.0160 0.6522 0.5122 0.060 Uiso 1 1 calc R U . . .
H9C H 0.0168 0.8333 0.5189 0.060 Uiso 1 1 calc R U . . .
C10 C 0.0401(2) 0.9648(3) 0.2944(2) 0.0390(6) Uani 1 1 d . . . . .
H10A H -0.0276 0.9058 0.2907 0.059 Uiso 1 1 calc R U . . .
H10B H 0.0257 1.0001 0.2214 0.059 Uiso 1 1 calc R U . . .
H10C H 0.0528 1.0554 0.3419 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4365(2) 0.6462(3) 0.65291(19) 0.0319(5) Uani 1 1 d . . . . .
H11A H 0.4580 0.5658 0.6139 0.048 Uiso 1 1 calc R U . . .
H11B H 0.4454 0.6047 0.7229 0.048 Uiso 1 1 calc R U . . .
H11C H 0.4873 0.7371 0.6650 0.048 Uiso 1 1 calc R U . . .
C12 C 0.37921(18) 0.8544(2) 0.48208(17) 0.0227(4) Uani 1 1 d . . . . .
O1 O 0.08462(13) 0.7054(2) 0.43962(13) 0.0289(3) Uani 1 1 d . . . . .
O2 O 0.14130(14) 0.8671(2) 0.33688(13) 0.0309(4) Uani 1 1 d . . . . .
O3 O 0.31724(13) 0.69169(19) 0.58973(12) 0.0242(3) Uani 1 1 d . . . . .
O4 O 0.44850(14) 0.83236(19) 0.44367(14) 0.0293(3) Uani 1 1 d . . . . .
O5 O 0.37734(15) 0.98079(19) 0.53550(14) 0.0294(4) Uani 1 1 d . . . . .
H5A H 0.429(3) 1.037(4) 0.540(3) 0.051(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C6 1.897(2) . ?
C1 O2 1.391(3) . ?
C1 O1 1.401(3) . ?
C1 C2 1.549(3) . ?
C1 H1 1.0000 . ?
C2 O3 1.427(2) . ?
C2 C3 1.521(3) . ?
C2 C12 1.542(3) . ?
C3 C8 1.388(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5B 0.9500 . ?
C6 C7 1.378(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 O1 1.425(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O2 1.432(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O3 1.436(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O4 1.218(3) . ?
C12 O5 1.313(3) . ?
O5 H5A 0.80(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 110.81(18) . . ?
O2 C1 C2 105.83(17) . . ?
O1 C1 C2 110.33(18) . . ?
O2 C1 H1 109.9 . . ?
O1 C1 H1 109.9 . . ?
C2 C1 H1 109.9 . . ?
O3 C2 C3 112.32(17) . . ?
O3 C2 C12 107.36(16) . . ?
C3 C2 C12 113.26(17) . . ?
O3 C2 C1 103.42(16) . . ?
C3 C2 C1 111.13(17) . . ?
C12 C2 C1 108.80(17) . . ?
C8 C3 C4 118.7(2) . . ?
C8 C3 C2 118.67(18) . . ?
C4 C3 C2 122.62(19) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5B 120.3 . . ?
C4 C5 H5B 120.3 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 Br1 118.33(18) . . ?
C5 C6 Br1 120.36(16) . . ?
C6 C7 C8 118.8(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C3 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O5 123.9(2) . . ?
O4 C12 C2 123.72(19) . . ?
O5 C12 C2 112.31(18) . . ?
C1 O1 C9 115.08(18) . . ?
C1 O2 C10 113.25(18) . . ?
C2 O3 C11 114.79(16) . . ?
C12 O5 H5A 109(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 O3 174.92(16) . . . . ?
O1 C1 C2 O3 -65.2(2) . . . . ?
O2 C1 C2 C3 -64.4(2) . . . . ?
O1 C1 C2 C3 55.6(2) . . . . ?
O2 C1 C2 C12 61.0(2) . . . . ?
O1 C1 C2 C12 -179.06(17) . . . . ?
O3 C2 C3 C8 19.3(3) . . . . ?
C12 C2 C3 C8 141.1(2) . . . . ?
C1 C2 C3 C8 -96.0(2) . . . . ?
O3 C2 C3 C4 -163.50(18) . . . . ?
C12 C2 C3 C4 -41.7(3) . . . . ?
C1 C2 C3 C4 81.2(2) . . . . ?
C8 C3 C4 C5 -2.0(3) . . . . ?
C2 C3 C4 C5 -179.24(19) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C4 C5 C6 Br1 -178.23(16) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
Br1 C6 C7 C8 177.97(17) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C4 C3 C8 C7 1.8(3) . . . . ?
C2 C3 C8 C7 179.1(2) . . . . ?
O3 C2 C12 O4 116.1(2) . . . . ?
C3 C2 C12 O4 -8.5(3) . . . . ?
C1 C2 C12 O4 -132.6(2) . . . . ?
O3 C2 C12 O5 -60.2(2) . . . . ?
C3 C2 C12 O5 175.22(18) . . . . ?
C1 C2 C12 O5 51.1(2) . . . . ?
O2 C1 O1 C9 -135.1(2) . . . . ?
C2 C1 O1 C9 108.1(2) . . . . ?
O1 C1 O2 C10 69.1(3) . . . . ?
C2 C1 O2 C10 -171.29(19) . . . . ?
C3 C2 O3 C11 73.2(2) . . . . ?
C12 C2 O3 C11 -51.9(2) . . . . ?
C1 C2 O3 C11 -166.87(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O4 0.80(4) 1.85(4) 2.646(2) 177(3) 3_676

_refine_diff_density_max         1.693
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

