# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_vqcol1_0m
_database_code_depnum_ccdc_archive 'CCDC 1419158'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.4933(8)
_cell_length_b                   10.7736(10)
_cell_length_c                   14.1815(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.8170(10)
_cell_angle_gamma                90.00
_cell_volume                     1296.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7692
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      30.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9422
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13529
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         29.99
_reflns_number_total             3658
_reflns_number_gt                3318
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.4261P] 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         3658
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O9' O 0.44149(9) 0.51715(7) 0.14367(5) 0.02015(16) Uani 1 1 d . . .
O5 O 0.03242(8) -0.19746(6) 0.16593(5) 0.01828(16) Uani 1 1 d . . .
O1' O -0.14934(9) 0.35033(7) 0.04412(6) 0.02268(18) Uani 1 1 d . . .
O8' O 0.43755(9) 0.34914(6) 0.23643(5) 0.01711(16) Uani 1 1 d . . .
O6' O 0.49967(8) 0.06483(7) 0.09912(5) 0.01851(16) Uani 1 1 d . . .
C9' C 0.39141(11) 0.41514(9) 0.15834(7) 0.01396(18) Uani 1 1 d . . .
C3' C 0.27073(10) 0.34201(8) 0.09705(6) 0.01097(17) Uani 1 1 d . . .
C7' C 0.29217(10) 0.21050(8) 0.13671(6) 0.01032(16) Uani 1 1 d . . .
C3 C 0.14778(10) 0.12850(8) 0.12869(6) 0.01071(17) Uani 1 1 d . . .
C4 C 0.16326(10) 0.00259(8) 0.15209(6) 0.01280(17) Uani 1 1 d . . .
H4 H 0.2628 -0.0301 0.1730 0.015 Uiso 1 1 calc R . .
C5 C 0.03120(11) -0.07434(8) 0.14437(7) 0.01370(18) Uani 1 1 d . . .
C7 C 0.18223(13) -0.25412(9) 0.18941(8) 0.0206(2) Uani 1 1 d . . .
H7A H 0.2497 -0.2475 0.1355 0.031 Uiso 1 1 calc R . .
H7B H 0.1666 -0.3419 0.2047 0.031 Uiso 1 1 calc R . .
H7C H 0.2327 -0.2118 0.2441 0.031 Uiso 1 1 calc R . .
C2' C 0.10762(11) 0.39847(8) 0.10896(7) 0.01325(17) Uani 1 1 d . . .
H2'1 H 0.0971 0.4208 0.1761 0.016 Uiso 1 1 calc R . .
H2'2 H 0.0977 0.4756 0.0712 0.016 Uiso 1 1 calc R . .
C1' C -0.02431(11) 0.31058(9) 0.07826(7) 0.01395(18) Uani 1 1 d . . .
C2 C 0.00093(10) 0.17681(8) 0.09752(6) 0.01211(17) Uani 1 1 d . . .
C1 C -0.12967(11) 0.09703(9) 0.08939(7) 0.01446(18) Uani 1 1 d . . .
H1 H -0.2290 0.1288 0.0671 0.017 Uiso 1 1 calc R . .
C6 C -0.11604(11) -0.02657(9) 0.11318(7) 0.01515(18) Uani 1 1 d . . .
H6 H -0.2058 -0.0792 0.1085 0.018 Uiso 1 1 calc R . .
C8' C 0.35269(11) 0.23187(9) 0.23889(6) 0.01418(18) Uani 1 1 d . . .
H8'1 H 0.2640 0.2373 0.2814 0.017 Uiso 1 1 calc R . .
H8'2 H 0.4238 0.1638 0.2607 0.017 Uiso 1 1 calc R . .
C6' C 0.42600(10) 0.15713(8) 0.07766(6) 0.01268(17) Uani 1 1 d . . .
C5' C 0.45192(11) 0.24184(9) -0.00583(7) 0.01513(18) Uani 1 1 d . . .
H5'1 H 0.4487 0.1939 -0.0654 0.018 Uiso 1 1 calc R . .
H5'2 H 0.5552 0.2842 0.0018 0.018 Uiso 1 1 calc R . .
C4' C 0.31685(11) 0.33636(9) -0.00636(6) 0.01383(18) Uani 1 1 d . . .
H4'1 H 0.2269 0.3085 -0.0481 0.017 Uiso 1 1 calc R . .
H4'2 H 0.3524 0.4186 -0.0280 0.017 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
O9' C9' 1.2003(12) . ?
O5 C5 1.3611(11) . ?
O5 C7 1.4356(12) . ?
O1' C1' 1.2226(12) . ?
O8' C9' 1.3576(12) . ?
O8' C8' 1.4559(11) . ?
O6' C6' 1.2059(12) . ?
C9' C3' 1.5294(12) . ?
C3' C2' 1.5299(12) . ?
C3' C7' 1.5319(12) . ?
C3' C4' 1.5377(13) . ?
C7' C3 1.5111(12) . ?
C7' C8' 1.5309(12) . ?
C7' C6' 1.5549(12) . ?
C3 C4 1.4011(12) . ?
C3 C2 1.4027(12) . ?
C4 C5 1.3946(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.4035(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2' C1' 1.5145(13) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C1' C2 1.4806(13) . ?
C2 C1 1.4036(12) . ?
C1 C6 1.3772(13) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C6' C5' 1.5195(13) . ?
C5' C4' 1.5337(13) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O5 C7 117.61(8) . . ?
C9' O8' C8' 110.53(7) . . ?
O9' C9' O8' 122.03(9) . . ?
O9' C9' C3' 127.33(9) . . ?
O8' C9' C3' 110.63(8) . . ?
C9' C3' C2' 108.52(7) . . ?
C9' C3' C7' 101.75(7) . . ?
C2' C3' C7' 114.78(7) . . ?
C9' C3' C4' 111.55(7) . . ?
C2' C3' C4' 113.29(7) . . ?
C7' C3' C4' 106.40(7) . . ?
C3 C7' C8' 113.12(7) . . ?
C3 C7' C3' 115.57(7) . . ?
C8' C7' C3' 103.69(7) . . ?
C3 C7' C6' 110.81(7) . . ?
C8' C7' C6' 110.19(7) . . ?
C3' C7' C6' 102.77(7) . . ?
C4 C3 C2 120.36(8) . . ?
C4 C3 C7' 118.80(8) . . ?
C2 C3 C7' 120.83(8) . . ?
C5 C4 C3 119.41(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
O5 C5 C4 124.35(9) . . ?
O5 C5 C6 115.15(8) . . ?
C4 C5 C6 120.50(8) . . ?
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 . . ?
C1' C2' C3' 112.39(8) . . ?
C1' C2' H2'1 109.1 . . ?
C3' C2' H2'1 109.1 . . ?
C1' C2' H2'2 109.1 . . ?
C3' C2' H2'2 109.1 . . ?
H2'1 C2' H2'2 107.9 . . ?
O1' C1' C2 121.94(9) . . ?
O1' C1' C2' 120.72(8) . . ?
C2 C1' C2' 117.20(8) . . ?
C3 C2 C1 119.05(8) . . ?
C3 C2 C1' 122.53(8) . . ?
C1 C2 C1' 118.31(8) . . ?
C6 C1 C2 121.02(9) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C1 C6 C5 119.65(8) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O8' C8' C7' 104.57(7) . . ?
O8' C8' H8'1 110.8 . . ?
C7' C8' H8'1 110.8 . . ?
O8' C8' H8'2 110.8 . . ?
C7' C8' H8'2 110.8 . . ?
H8'1 C8' H8'2 108.9 . . ?
O6' C6' C5' 126.78(9) . . ?
O6' C6' C7' 123.57(8) . . ?
C5' C6' C7' 109.59(7) . . ?
C6' C5' C4' 105.41(7) . . ?
C6' C5' H5'1 110.7 . . ?
C4' C5' H5'1 110.7 . . ?
C6' C5' H5'2 110.7 . . ?
C4' C5' H5'2 110.7 . . ?
H5'1 C5' H5'2 108.8 . . ?
C5' C4' C3' 104.30(7) . . ?
C5' C4' H4'1 110.9 . . ?
C3' C4' H4'1 110.9 . . ?
C5' C4' H4'2 110.9 . . ?
C3' C4' H4'2 110.9 . . ?
H4'1 C4' H4'2 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8' O8' C9' O9' 177.02(9) . . . . ?
C8' O8' C9' C3' -2.30(10) . . . . ?
O9' C9' C3' C2' -74.06(12) . . . . ?
O8' C9' C3' C2' 105.22(9) . . . . ?
O9' C9' C3' C7' 164.53(10) . . . . ?
O8' C9' C3' C7' -16.19(9) . . . . ?
O9' C9' C3' C4' 51.44(13) . . . . ?
O8' C9' C3' C4' -129.28(8) . . . . ?
C9' C3' C7' C3 151.32(7) . . . . ?
C2' C3' C7' C3 34.36(10) . . . . ?
C4' C3' C7' C3 -91.79(9) . . . . ?
C9' C3' C7' C8' 26.94(8) . . . . ?
C2' C3' C7' C8' -90.02(8) . . . . ?
C4' C3' C7' C8' 143.83(7) . . . . ?
C9' C3' C7' C6' -87.86(8) . . . . ?
C2' C3' C7' C6' 155.18(7) . . . . ?
C4' C3' C7' C6' 29.04(8) . . . . ?
C8' C7' C3 C4 -68.83(11) . . . . ?
C3' C7' C3 C4 171.84(8) . . . . ?
C6' C7' C3 C4 55.48(10) . . . . ?
C8' C7' C3 C2 111.79(9) . . . . ?
C3' C7' C3 C2 -7.53(12) . . . . ?
C6' C7' C3 C2 -123.90(9) . . . . ?
C2 C3 C4 C5 -0.17(13) . . . . ?
C7' C3 C4 C5 -179.55(8) . . . . ?
C7 O5 C5 C4 -6.27(14) . . . . ?
C7 O5 C5 C6 174.10(9) . . . . ?
C3 C4 C5 O5 -179.41(8) . . . . ?
C3 C4 C5 C6 0.20(14) . . . . ?
C9' C3' C2' C1' -161.24(7) . . . . ?
C7' C3' C2' C1' -48.22(10) . . . . ?
C4' C3' C2' C1' 74.28(10) . . . . ?
C3' C2' C1' O1' -148.06(9) . . . . ?
C3' C2' C1' C2 36.10(11) . . . . ?
C4 C3 C2 C1 -0.54(13) . . . . ?
C7' C3 C2 C1 178.83(8) . . . . ?
C4 C3 C2 C1' 175.65(8) . . . . ?
C7' C3 C2 C1' -4.98(13) . . . . ?
O1' C1' C2 C3 174.15(9) . . . . ?
C2' C1' C2 C3 -10.06(13) . . . . ?
O1' C1' C2 C1 -9.63(14) . . . . ?
C2' C1' C2 C1 166.15(8) . . . . ?
C3 C2 C1 C6 1.25(14) . . . . ?
C1' C2 C1 C6 -175.10(9) . . . . ?
C2 C1 C6 C5 -1.23(14) . . . . ?
O5 C5 C6 C1 -179.86(8) . . . . ?
C4 C5 C6 C1 0.49(14) . . . . ?
C9' O8' C8' C7' 20.03(10) . . . . ?
C3 C7' C8' O8' -155.15(7) . . . . ?
C3' C7' C8' O8' -29.19(9) . . . . ?
C6' C7' C8' O8' 80.20(9) . . . . ?
C3 C7' C6' O6' -71.24(11) . . . . ?
C8' C7' C6' O6' 54.73(11) . . . . ?
C3' C7' C6' O6' 164.72(9) . . . . ?
C3 C7' C6' C5' 111.41(8) . . . . ?
C8' C7' C6' C5' -122.62(8) . . . . ?
C3' C7' C6' C5' -12.63(9) . . . . ?
O6' C6' C5' C4' 174.31(9) . . . . ?
C7' C6' C5' C4' -8.44(9) . . . . ?
C6' C5' C4' C3' 26.16(9) . . . . ?
C9' C3' C4' C5' 75.10(9) . . . . ?
C2' C3' C4' C5' -162.09(7) . . . . ?
C7' C3' C4' C5' -35.05(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_mo_vqc4_0m
_database_code_depnum_ccdc_archive 'CCDC 1446962'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Br O5'
_chemical_formula_sum            'C16 H13 Br O5'
_chemical_formula_weight         365.17
_chemical_absolute_configuration ad

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.1765(7)
_cell_length_b                   10.7366(9)
_cell_length_c                   16.4944(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1448.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8154
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      29.94

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3941
_exptl_absorpt_correction_T_max  0.7074
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15416
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         30.55
_reflns_number_total             4129
_reflns_number_gt                3810
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(7)
_refine_ls_number_reflns         4129
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0514
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.002
_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 0.10311(2) 0.963430(19) 0.626795(13) 0.01822(6) Uani 1 1 d . . .
O9' O 0.4843(2) 1.10780(15) 0.66584(10) 0.0248(4) Uani 1 1 d . . .
O5 O 0.3287(2) 0.38497(14) 0.50772(10) 0.0198(3) Uani 1 1 d . . .
O6' O 0.71900(19) 0.65753(16) 0.61948(11) 0.0284(4) Uani 1 1 d . . .
O1' O 0.0842(2) 0.75265(16) 0.78749(9) 0.0210(3) Uani 1 1 d . . .
O8' O 0.5139(2) 0.97845(14) 0.56088(10) 0.0215(3) Uani 1 1 d . . .
C9' C 0.4757(3) 1.0044(2) 0.63861(13) 0.0173(4) Uani 1 1 d . . .
C3' C 0.4257(2) 0.88634(19) 0.68390(12) 0.0123(4) Uani 1 1 d . . .
C7' C 0.4683(2) 0.78201(17) 0.62391(14) 0.0123(3) Uani 1 1 d . . .
C3 C 0.3524(2) 0.67242(17) 0.62025(12) 0.0114(3) Uani 1 1 d . . .
C4 C 0.3838(3) 0.57750(18) 0.56600(12) 0.0135(4) Uani 1 1 d . . .
H4 H 0.4751 0.5836 0.5306 0.016 Uiso 1 1 calc R . .
C5 C 0.2828(2) 0.47233(19) 0.56244(12) 0.0147(4) Uani 1 1 d . . .
C7 C 0.2328(3) 0.2743(2) 0.50139(16) 0.0250(5) Uani 1 1 d . . .
H7A H 0.2362 0.2290 0.5529 0.038 Uiso 1 1 calc R . .
H7B H 0.2768 0.2214 0.4582 0.038 Uiso 1 1 calc R . .
H7C H 0.1193 0.2965 0.4887 0.038 Uiso 1 1 calc R . .
C2' C 0.2471(2) 0.89290(19) 0.71074(12) 0.0124(4) Uani 1 1 d . . .
H2' H 0.2399 0.9461 0.7604 0.015 Uiso 1 1 calc R . .
C4' C 0.5358(2) 0.8703(2) 0.75899(13) 0.0145(4) Uani 1 1 d . . .
H4'1 H 0.5583 0.9518 0.7848 0.017 Uiso 1 1 calc R . .
H4'2 H 0.4836 0.8148 0.7993 0.017 Uiso 1 1 calc R . .
C5' C 0.6924(3) 0.8127(2) 0.72640(14) 0.0185(4) Uani 1 1 d . . .
H5'1 H 0.7717 0.8782 0.7110 0.022 Uiso 1 1 calc R . .
H5'2 H 0.7433 0.7580 0.7676 0.022 Uiso 1 1 calc R . .
C6' C 0.6411(2) 0.7378(2) 0.65269(14) 0.0177(4) Uani 1 1 d . . .
C6 C 0.1469(2) 0.4629(2) 0.61364(12) 0.0154(4) Uani 1 1 d . . .
H6 H 0.0770 0.3923 0.6113 0.018 Uiso 1 1 calc R . .
C1 C 0.1161(3) 0.55952(18) 0.66818(12) 0.0151(4) Uani 1 1 d . . .
H1 H 0.0242 0.5538 0.7032 0.018 Uiso 1 1 calc R . .
C2 C 0.2165(2) 0.66393(18) 0.67252(12) 0.0125(4) Uani 1 1 d . . .
C1' C 0.1757(2) 0.7658(2) 0.72990(13) 0.0141(4) Uani 1 1 d . . .
C8' C 0.4827(3) 0.84979(19) 0.54122(13) 0.0173(4) Uani 1 1 d . . .
H8'1 H 0.5737 0.8147 0.5089 0.021 Uiso 1 1 calc R . .
H8'2 H 0.3800 0.8415 0.5099 0.021 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2' 1.969(2) . ?
O9' C9' 1.199(3) . ?
O5 C5 1.355(2) . ?
O5 C7 1.428(3) . ?
O6' C6' 1.204(3) . ?
O1' C1' 1.217(2) . ?
O8' C9' 1.349(3) . ?
O8' C8' 1.442(3) . ?
C9' C3' 1.527(3) . ?
C3' C2' 1.527(3) . ?
C3' C7' 1.535(3) . ?
C3' C4' 1.541(3) . ?
C7' C3 1.512(3) . ?
C7' C8' 1.550(3) . ?
C7' C6' 1.564(3) . ?
C3 C4 1.380(3) . ?
C3 C2 1.409(3) . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2' C1' 1.518(3) . ?
C2' H2' 1.0000 . ?
C4' C5' 1.520(3) . ?
C4' H4'1 0.9900 . ?
C4' H4'2 0.9900 . ?
C5' C6' 1.517(3) . ?
C5' H5'1 0.9900 . ?
C5' H5'2 0.9900 . ?
C6 C1 1.396(3) . ?
C6 H6 0.9500 . ?
C1 C2 1.392(3) . ?
C1 H1 0.9500 . ?
C2 C1' 1.484(3) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O5 C7 118.20(18) . . ?
C9' O8' C8' 111.79(17) . . ?
O9' C9' O8' 122.3(2) . . ?
O9' C9' C3' 126.9(2) . . ?
O8' C9' C3' 110.80(17) . . ?
C9' C3' C2' 111.07(17) . . ?
C9' C3' C7' 103.28(16) . . ?
C2' C3' C7' 115.97(16) . . ?
C9' C3' C4' 109.22(17) . . ?
C2' C3' C4' 109.32(16) . . ?
C7' C3' C4' 107.68(17) . . ?
C3 C7' C3' 116.82(16) . . ?
C3 C7' C8' 112.19(17) . . ?
C3' C7' C8' 103.99(16) . . ?
C3 C7' C6' 110.01(16) . . ?
C3' C7' C6' 103.36(17) . . ?
C8' C7' C6' 109.92(17) . . ?
C4 C3 C2 119.70(18) . . ?
C4 C3 C7' 118.94(17) . . ?
C2 C3 C7' 121.33(17) . . ?
C3 C4 C5 120.85(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O5 C5 C6 124.9(2) . . ?
O5 C5 C4 115.00(18) . . ?
C6 C5 C4 120.09(19) . . ?
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 . . ?
C1' C2' C3' 112.77(17) . . ?
C1' C2' Br1 105.19(13) . . ?
C3' C2' Br1 112.67(14) . . ?
C1' C2' H2' 108.7 . . ?
C3' C2' H2' 108.7 . . ?
Br1 C2' H2' 108.7 . . ?
C5' C4' C3' 104.68(17) . . ?
C5' C4' H4'1 110.8 . . ?
C3' C4' H4'1 110.8 . . ?
C5' C4' H4'2 110.8 . . ?
C3' C4' H4'2 110.8 . . ?
H4'1 C4' H4'2 108.9 . . ?
C6' C5' C4' 105.45(17) . . ?
C6' C5' H5'1 110.7 . . ?
C4' C5' H5'1 110.7 . . ?
C6' C5' H5'2 110.7 . . ?
C4' C5' H5'2 110.7 . . ?
H5'1 C5' H5'2 108.8 . . ?
O6' C6' C5' 126.7(2) . . ?
O6' C6' C7' 123.9(2) . . ?
C5' C6' C7' 109.41(17) . . ?
C5 C6 C1 118.61(19) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C2 C1 C6 121.67(19) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.08(18) . . ?
C1 C2 C1' 119.56(18) . . ?
C3 C2 C1' 121.33(18) . . ?
O1' C1' C2 123.4(2) . . ?
O1' C1' C2' 120.22(19) . . ?
C2 C1' C2' 116.30(17) . . ?
O8' C8' C7' 105.38(16) . . ?
O8' C8' H8'1 110.7 . . ?
C7' C8' H8'1 110.7 . . ?
O8' C8' H8'2 110.7 . . ?
C7' C8' H8'2 110.7 . . ?
H8'1 C8' H8'2 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8' O8' C9' O9' -175.9(2) . . . . ?
C8' O8' C9' C3' 5.1(2) . . . . ?
O9' C9' C3' C2' 65.4(3) . . . . ?
O8' C9' C3' C2' -115.74(19) . . . . ?
O9' C9' C3' C7' -169.7(2) . . . . ?
O8' C9' C3' C7' 9.2(2) . . . . ?
O9' C9' C3' C4' -55.3(3) . . . . ?
O8' C9' C3' C4' 123.61(18) . . . . ?
C9' C3' C7' C3 -142.67(18) . . . . ?
C2' C3' C7' C3 -20.9(3) . . . . ?
C4' C3' C7' C3 101.8(2) . . . . ?
C9' C3' C7' C8' -18.5(2) . . . . ?
C2' C3' C7' C8' 103.26(19) . . . . ?
C4' C3' C7' C8' -133.95(17) . . . . ?
C9' C3' C7' C6' 96.39(18) . . . . ?
C2' C3' C7' C6' -141.89(17) . . . . ?
C4' C3' C7' C6' -19.1(2) . . . . ?
C3' C7' C3 C4 178.64(18) . . . . ?
C8' C7' C3 C4 58.7(2) . . . . ?
C6' C7' C3 C4 -64.0(2) . . . . ?
C3' C7' C3 C2 -3.2(3) . . . . ?
C8' C7' C3 C2 -123.1(2) . . . . ?
C6' C7' C3 C2 114.2(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C7' C3 C4 C5 177.86(18) . . . . ?
C7 O5 C5 C6 -0.3(3) . . . . ?
C7 O5 C5 C4 179.20(18) . . . . ?
C3 C4 C5 O5 -178.78(18) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C9' C3' C2' C1' 160.72(17) . . . . ?
C7' C3' C2' C1' 43.2(2) . . . . ?
C4' C3' C2' C1' -78.7(2) . . . . ?
C9' C3' C2' Br1 41.8(2) . . . . ?
C7' C3' C2' Br1 -75.7(2) . . . . ?
C4' C3' C2' Br1 162.42(13) . . . . ?
C9' C3' C4' C5' -80.9(2) . . . . ?
C2' C3' C4' C5' 157.35(17) . . . . ?
C7' C3' C4' C5' 30.6(2) . . . . ?
C3' C4' C5' C6' -29.1(2) . . . . ?
C4' C5' C6' O6' -163.0(2) . . . . ?
C4' C5' C6' C7' 17.8(2) . . . . ?
C3 C7' C6' O6' 56.2(3) . . . . ?
C3' C7' C6' O6' -178.4(2) . . . . ?
C8' C7' C6' O6' -67.9(3) . . . . ?
C3 C7' C6' C5' -124.65(19) . . . . ?
C3' C7' C6' C5' 0.8(2) . . . . ?
C8' C7' C6' C5' 111.32(19) . . . . ?
O5 C5 C6 C1 178.85(18) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C1 C2 C1' 178.19(18) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C7' C3 C2 C1 -178.30(18) . . . . ?
C4 C3 C2 C1' -178.05(18) . . . . ?
C7' C3 C2 C1' 3.8(3) . . . . ?
C1 C2 C1' O1' 18.8(3) . . . . ?
C3 C2 C1' O1' -163.3(2) . . . . ?
C1 C2 C1' C2' -157.85(18) . . . . ?
C3 C2 C1' C2' 20.1(3) . . . . ?
C3' C2' C1' O1' 140.4(2) . . . . ?
Br1 C2' C1' O1' -96.5(2) . . . . ?
C3' C2' C1' C2 -42.9(2) . . . . ?
Br1 C2' C1' C2 80.26(18) . . . . ?
C9' O8' C8' C7' -17.2(2) . . . . ?
C3 C7' C8' O8' 148.99(16) . . . . ?
C3' C7' C8' O8' 21.8(2) . . . . ?
C6' C7' C8' O8' -88.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        30.55
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.082
