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# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_cpd1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 O6'
_chemical_formula_weight         318.31

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                   8.2815(2)
_cell_length_b                   8.4808(2)
_cell_length_c                   13.3432(3)
_cell_angle_alpha                104.8350(10)
_cell_angle_beta                 95.4060(10)
_cell_angle_gamma                114.0380(10)
_cell_volume                     806.15(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18026
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0205
_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       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         30.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4878
_reflns_number_gt                3744
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0984P)²+0.1276P] 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         4878
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C2 C 0.4797(2) 0.70152(19) 0.60215(11) 0.0418(3) Uani 1 1 d . . . . .
C3 C 0.33984(18) 0.54597(16) 0.59878(9) 0.0352(3) Uani 1 1 d . . . . .
C4 C 0.32304(16) 0.47712(15) 0.69302(9) 0.0308(2) Uani 1 1 d . . . . .
H4 H 0.2926 0.3472 0.6667 0.037 Uiso 1 1 calc R U . . .
C4A C 0.50279(16) 0.57275(15) 0.77304(9) 0.0322(2) Uani 1 1 d . . . . .
C5 C 0.53684(18) 0.50874(18) 0.85503(10) 0.0380(3) Uani 1 1 d . . . . .
H5 H 0.4477 0.4021 0.8601 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7006(2) 0.6006(2) 0.92899(11) 0.0454(3) Uani 1 1 d . . . . .
H6 H 0.7200 0.5565 0.9836 0.055 Uiso 1 1 calc R U . . .
C7 C 0.8354(2) 0.7580(2) 0.92176(12) 0.0504(4) Uani 1 1 d . . . . .
H7 H 0.9456 0.8195 0.9715 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8067(2) 0.8241(2) 0.84079(13) 0.0497(3) Uani 1 1 d . . . . .
H8 H 0.8969 0.9297 0.8353 0.060 Uiso 1 1 calc R U . . .
C8A C 0.64130(18) 0.73028(17) 0.76785(11) 0.0394(3) Uani 1 1 d . . . . .
C9 C 0.1933(2) 0.43683(19) 0.50140(10) 0.0415(3) Uani 1 1 d . . . . .
C10 C -0.0566(3) 0.1484(3) 0.41434(14) 0.0666(5) Uani 1 1 d . . . . .
H103 H -0.0088 0.1392 0.3514 0.100 Uiso 1 1 calc R U . . .
H102 H -0.1440 0.1947 0.4083 0.100 Uiso 1 1 calc R U . . .
H101 H -0.1139 0.0299 0.4223 0.100 Uiso 1 1 calc R U . . .
C11 C 0.5093(3) 0.7933(3) 0.51882(15) 0.0615(5) Uani 1 1 d . . . . .
H111 H 0.4533 0.8738 0.5280 0.092 Uiso 1 1 calc R U . . .
H113 H 0.4564 0.7028 0.4496 0.092 Uiso 1 1 calc R U . . .
H112 H 0.6371 0.8622 0.5254 0.092 Uiso 1 1 calc R U . . .
C1' C 0.23004(17) 0.67134(16) 0.83216(10) 0.0358(3) Uani 1 1 d . . . . .
C2' C 0.16354(16) 0.49335(15) 0.74140(9) 0.0329(2) Uani 1 1 d . . . . .
H2' H 0.0799 0.4952 0.6852 0.040 Uiso 1 1 calc R U . . .
C3' C 0.05528(19) 0.33225(17) 0.77809(11) 0.0413(3) Uani 1 1 d . . . . .
C4' C -0.1211(3) 0.3158(3) 0.8012(2) 0.0825(7) Uani 1 1 d . . . . .
H4'1 H -0.1069 0.3650 0.8765 0.124 Uiso 1 1 calc R U . . .
H4'3 H -0.2084 0.1896 0.7764 0.124 Uiso 1 1 calc R U . . .
H4'2 H -0.1623 0.3822 0.7656 0.124 Uiso 1 1 calc R U . . .
C5' C 0.3590(3) 0.9903(2) 0.86986(17) 0.0761(6) Uani 1 1 d . . . . .
H5'1 H 0.4843 1.0282 0.8994 0.114 Uiso 1 1 calc R U . . .
H5'3 H 0.2939 0.9896 0.9257 0.114 Uiso 1 1 calc R U . . .
H5'2 H 0.3499 1.0736 0.8352 0.114 Uiso 1 1 calc R U . . .
O1 O 0.62302(15) 0.80309(13) 0.68791(9) 0.0517(3) Uani 1 1 d . . . . .
O2 O 0.16429(19) 0.48417(19) 0.42669(9) 0.0664(4) Uani 1 1 d . . . . .
O3 O 0.08910(15) 0.27062(14) 0.50593(8) 0.0500(3) Uani 1 1 d . . . . .
O4 O 0.28253(16) 0.81027(13) 0.79388(9) 0.0527(3) Uani 1 1 d . . . . .
O5 O 0.23806(18) 0.68523(15) 0.92416(8) 0.0576(3) Uani 1 1 d . . . . .
O6 O 0.10803(15) 0.22158(14) 0.78506(10) 0.0542(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
C2 C3 1.3415(19) . ?
C2 O1 1.3661(18) . ?
C2 C11 1.4971(18) . ?
C3 C9 1.4796(18) . ?
C3 C4 1.5113(15) . ?
C4 C4A 1.5124(16) . ?
C4 C2' 1.5633(17) . ?
C4 H4 0.9800 . ?
C4A C8A 1.3855(17) . ?
C4A C5 1.3933(16) . ?
C5 C6 1.3834(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3863(19) . ?
C8 H8 0.9300 . ?
C8A O1 1.3874(16) . ?
C9 O2 1.2047(15) . ?
C9 O3 1.3409(18) . ?
C10 O3 1.4415(18) . ?
C10 H103 0.9600 . ?
C10 H102 0.9600 . ?
C10 H101 0.9600 . ?
C11 H111 0.9600 . ?
C11 H113 0.9600 . ?
C11 H112 0.9600 . ?
C1' O5 1.1956(16) . ?
C1' O4 1.3308(16) . ?
C1' C2' 1.5197(16) . ?
C2' C3' 1.5288(17) . ?
C2' H2' 0.9800 . ?
C3' O6 1.2049(17) . ?
C3' C4' 1.479(2) . ?
C4' H4'1 0.9600 . ?
C4' H4'3 0.9600 . ?
C4' H4'2 0.9600 . ?
C5' O4 1.4349(19) . ?
C5' H5'1 0.9600 . ?
C5' H5'3 0.9600 . ?
C5' H5'2 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
C3 C2 O1 122.77(11) . . ?
C3 C2 C11 128.44(14) . . ?
O1 C2 C11 108.79(13) . . ?
C2 C3 C9 120.25(11) . . ?
C2 C3 C4 122.17(11) . . ?
C9 C3 C4 117.58(11) . . ?
C3 C4 C4A 110.44(10) . . ?
C3 C4 C2' 110.46(9) . . ?
C4A C4 C2' 113.47(9) . . ?
C3 C4 H4 107.4 . . ?
C4A C4 H4 107.4 . . ?
C2' C4 H4 107.4 . . ?
C8A C4A C5 117.04(11) . . ?
C8A C4A C4 120.75(10) . . ?
C5 C4A C4 122.21(11) . . ?
C6 C5 C4A 121.33(12) . . ?
C6 C5 H5 119.3 . . ?
C4A C5 H5 119.3 . . ?
C7 C6 C5 120.07(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.05(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C8A 118.91(13) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
C4A C8A C8 122.59(12) . . ?
C4A C8A O1 121.67(12) . . ?
C8 C8A O1 115.74(12) . . ?
O2 C9 O3 122.21(13) . . ?
O2 C9 C3 127.18(14) . . ?
O3 C9 C3 110.60(10) . . ?
O3 C10 H103 109.5 . . ?
O3 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
O3 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
H102 C10 H101 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
H113 C11 H112 109.5 . . ?
O5 C1' O4 125.07(12) . . ?
O5 C1' C2' 125.36(12) . . ?
O4 C1' C2' 109.55(10) . . ?
C1' C2' C3' 109.99(10) . . ?
C1' C2' C4 111.44(10) . . ?
C3' C2' C4 113.46(10) . . ?
C1' C2' H2' 107.2 . . ?
C3' C2' H2' 107.2 . . ?
C4 C2' H2' 107.2 . . ?
O6 C3' C4' 121.63(14) . . ?
O6 C3' C2' 121.94(12) . . ?
C4' C3' C2' 116.39(14) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
H4'3 C4' H4'2 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
H5'3 C5' H5'2 109.5 . . ?
C2 O1 C8A 119.18(10) . . ?
C9 O3 C10 116.22(12) . . ?
C1' O4 C5' 116.93(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 C9 -176.74(12) . . . . ?
C11 C2 C3 C9 3.3(2) . . . . ?
O1 C2 C3 C4 4.4(2) . . . . ?
C11 C2 C3 C4 -175.62(14) . . . . ?
C2 C3 C4 C4A -16.34(16) . . . . ?
C9 C3 C4 C4A 164.75(10) . . . . ?
C2 C3 C4 C2' 110.02(13) . . . . ?
C9 C3 C4 C2' -68.90(13) . . . . ?
C3 C4 C4A C8A 14.89(15) . . . . ?
C2' C4 C4A C8A -109.76(13) . . . . ?
C3 C4 C4A C5 -165.55(11) . . . . ?
C2' C4 C4A C5 69.81(14) . . . . ?
C8A C4A C5 C6 1.18(19) . . . . ?
C4 C4A C5 C6 -178.40(12) . . . . ?
C4A C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C8A 0.2(2) . . . . ?
C5 C4A C8A C8 -0.9(2) . . . . ?
C4 C4A C8A C8 178.72(12) . . . . ?
C5 C4A C8A O1 178.45(12) . . . . ?
C4 C4A C8A O1 -1.96(19) . . . . ?
C7 C8 C8A C4A 0.2(2) . . . . ?
C7 C8 C8A O1 -179.15(13) . . . . ?
C2 C3 C9 O2 -13.9(2) . . . . ?
C4 C3 C9 O2 165.08(14) . . . . ?
C2 C3 C9 O3 166.84(12) . . . . ?
C4 C3 C9 O3 -14.22(16) . . . . ?
O5 C1' C2' C3' 17.33(18) . . . . ?
O4 C1' C2' C3' -164.26(11) . . . . ?
O5 C1' C2' C4 -109.40(15) . . . . ?
O4 C1' C2' C4 69.02(13) . . . . ?
C3 C4 C2' C1' -93.82(11) . . . . ?
C4A C4 C2' C1' 30.82(12) . . . . ?
C3 C4 C2' C3' 141.38(10) . . . . ?
C4A C4 C2' C3' -93.99(11) . . . . ?
C1' C2' C3' O6 -113.84(14) . . . . ?
C4 C2' C3' O6 11.75(17) . . . . ?
C1' C2' C3' C4' 68.15(18) . . . . ?
C4 C2' C3' C4' -166.26(15) . . . . ?
C3 C2 O1 C8A 10.7(2) . . . . ?
C11 C2 O1 C8A -169.29(13) . . . . ?
C4A C8A O1 C2 -11.8(2) . . . . ?
C8 C8A O1 C2 167.54(13) . . . . ?
O2 C9 O3 C10 2.2(2) . . . . ?
C3 C9 O3 C10 -178.46(13) . . . . ?
O5 C1' O4 C5' 1.8(2) . . . . ?
C2' C1' O4 C5' -176.65(15) . . . . ?

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
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 952576'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd2
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 O7'
_chemical_formula_sum            'C18 H20 O7'

_chemical_formula_weight         348.34

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                   9.0528(4)
_cell_length_b                   9.1110(4)
_cell_length_c                   11.9970(5)
_cell_angle_alpha                80.134(2)
_cell_angle_beta                 68.141(2)
_cell_angle_gamma                72.313(2)
_cell_volume                     873.06(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9751
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.885
_diffrn_reflns_theta_max         30.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5278
_reflns_number_gt                3784
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0967P)²+0.1324P] 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         5278
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1770
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C2 C 0.28456(16) 0.40001(15) 0.51476(11) 0.0374(3) Uani 1 1 d . . . . .
C3 C 0.26381(15) 0.27541(14) 0.48259(10) 0.0331(3) Uani 1 1 d . . . . .
C4 C 0.21945(16) 0.27832(13) 0.37226(11) 0.0334(3) Uani 1 1 d . . . . .
H4 H 0.1256 0.2332 0.3971 0.040 Uiso 1 1 calc R U . . .
C4A C 0.16509(16) 0.44237(14) 0.32399(11) 0.0356(3) Uani 1 1 d . . . . .
C5 C 0.09418(18) 0.47605(17) 0.23515(13) 0.0444(3) Uani 1 1 d . . . . .
H5 H 0.0753 0.3970 0.2069 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0508(2) 0.62734(19) 0.18753(14) 0.0515(4) Uani 1 1 d . . . . .
C7 C 0.0783(2) 0.74582(17) 0.22883(15) 0.0553(4) Uani 1 1 d . . . . .
H7 H 0.0512 0.8465 0.1964 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1461(2) 0.71323(16) 0.31808(15) 0.0506(4) Uani 1 1 d . . . . .
H8 H 0.1633 0.7925 0.3474 0.061 Uiso 1 1 calc R U . . .
C8A C 0.18914(17) 0.56289(15) 0.36480(12) 0.0388(3) Uani 1 1 d . . . . .
C9 C 0.28533(17) 0.12794(15) 0.55562(11) 0.0375(3) Uani 1 1 d . . . . .
C10 C 0.2390(3) -0.12070(18) 0.59065(17) 0.0610(4) Uani 1 1 d . . . . .
H101 H 0.3527 -0.1718 0.5795 0.091 Uiso 1 1 calc R U . . .
H102 H 0.1932 -0.1824 0.5618 0.091 Uiso 1 1 calc R U . . .
H103 H 0.1789 -0.1068 0.6747 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3362(2) 0.41260(19) 0.61625(14) 0.0509(4) Uani 1 1 d . . . . .
H111 H 0.4539 0.3744 0.5939 0.076 Uiso 1 1 calc R U . . .
H112 H 0.2844 0.3528 0.6858 0.076 Uiso 1 1 calc R U . . .
H113 H 0.3036 0.5188 0.6345 0.076 Uiso 1 1 calc R U . . .
C12 C -0.0629(4) 0.7957(3) 0.0474(2) 0.1051(10) Uani 1 1 d . . . . .
H121 H 0.0347 0.8307 0.0046 0.158 Uiso 1 1 calc R U . . .
H122 H -0.1363 0.8648 0.1089 0.158 Uiso 1 1 calc R U . . .
H123 H -0.1167 0.7937 -0.0075 0.158 Uiso 1 1 calc R U . . .
C1' C 0.46579(19) 0.26724(15) 0.17603(12) 0.0421(3) Uani 1 1 d . . . . .
C2' C 0.36679(17) 0.17447(14) 0.27640(11) 0.0356(3) Uani 1 1 d . . . . .
H2' H 0.4409 0.1080 0.3178 0.043 Uiso 1 1 calc R U . . .
C3' C 0.3134(2) 0.06877(15) 0.22118(13) 0.0458(3) Uani 1 1 d . . . . .
C4' C 0.4458(3) -0.06990(19) 0.16577(17) 0.0622(5) Uani 1 1 d . . . . .
H4'1 H 0.4753 -0.1406 0.2279 0.093 Uiso 1 1 calc R U . . .
H4'2 H 0.5410 -0.0381 0.1112 0.093 Uiso 1 1 calc R U . . .
H4'3 H 0.4060 -0.1197 0.1227 0.093 Uiso 1 1 calc R U . . .
C5' C 0.6192(3) 0.4517(3) 0.13036(18) 0.0753(6) Uani 1 1 d . . . . .
H5'1 H 0.6785 0.4059 0.0544 0.113 Uiso 1 1 calc R U . . .
H5'2 H 0.6950 0.4747 0.1591 0.113 Uiso 1 1 calc R U . . .
H5'3 H 0.5390 0.5453 0.1204 0.113 Uiso 1 1 calc R U . . .
O1 O 0.25784(14) 0.54135(11) 0.45426(10) 0.0457(3) Uani 1 1 d . . . . .
O2 O 0.34680(16) 0.09508(13) 0.63344(10) 0.0556(3) Uani 1 1 d . . . . .
O3 O 0.22725(14) 0.02815(11) 0.52434(9) 0.0470(3) Uani 1 1 d . . . . .
O4 O 0.53658(14) 0.34511(13) 0.21649(9) 0.0486(3) Uani 1 1 d . . . . .
O5 O 0.4763(2) 0.27370(17) 0.07276(10) 0.0765(5) Uani 1 1 d . . . . .
O6 O 0.17337(18) 0.09384(14) 0.22441(13) 0.0677(4) Uani 1 1 d . . . . .
O7 O -0.01896(19) 0.64544(17) 0.10099(12) 0.0755(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
C2 C3 1.3441(18) . ?
C2 O1 1.3655(15) . ?
C2 C11 1.4896(19) . ?
C3 C9 1.4750(16) . ?
C3 C4 1.5136(17) . ?
C4 C4A 1.5100(16) . ?
C4 C2' 1.5687(18) . ?
C4 H4 0.9800 . ?
C4A C8A 1.3791(19) . ?
C4A C5 1.3856(18) . ?
C5 C6 1.3960(19) . ?
C5 H5 0.9300 . ?
C6 O7 1.367(2) . ?
C6 C7 1.383(3) . ?
C7 C8 1.372(2) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3846(18) . ?
C8 H8 0.9300 . ?
C8A O1 1.3884(17) . ?
C9 O2 1.2086(16) . ?
C9 O3 1.3409(17) . ?
C10 O3 1.4454(16) . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?
C11 H111 0.9600 . ?
C11 H112 0.9600 . ?
C11 H113 0.9600 . ?
C12 O7 1.416(2) . ?
C12 H121 0.9600 . ?
C12 H122 0.9600 . ?
C12 H123 0.9600 . ?
C1' O5 1.1992(17) . ?
C1' O4 1.3325(18) . ?
C1' C2' 1.5084(19) . ?
C2' C3' 1.5295(18) . ?
C2' H2' 0.9800 . ?
C3' O6 1.205(2) . ?
C3' C4' 1.500(2) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.447(2) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 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
C3 C2 O1 122.45(11) . . ?
C3 C2 C11 128.73(12) . . ?
O1 C2 C11 108.82(11) . . ?
C2 C3 C9 119.93(11) . . ?
C2 C3 C4 122.70(11) . . ?
C9 C3 C4 117.37(10) . . ?
C4A C4 C3 110.62(10) . . ?
C4A C4 C2' 113.25(10) . . ?
C3 C4 C2' 109.99(10) . . ?
C4A C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C2' C4 H4 107.6 . . ?
C8A C4A C5 117.99(12) . . ?
C8A C4A C4 120.76(11) . . ?
C5 C4A C4 121.23(12) . . ?
C4A C5 C6 120.77(14) . . ?
C4A C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O7 C6 C7 124.80(14) . . ?
O7 C6 C5 115.09(16) . . ?
C7 C6 C5 120.11(14) . . ?
C8 C7 C6 119.27(13) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C8A 120.32(15) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
C4A C8A C8 121.53(13) . . ?
C4A C8A O1 122.39(11) . . ?
C8 C8A O1 116.08(13) . . ?
O2 C9 O3 122.19(12) . . ?
O2 C9 C3 127.01(13) . . ?
O3 C9 C3 110.80(10) . . ?
O3 C10 H101 109.5 . . ?
O3 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
O3 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
O7 C12 H121 109.5 . . ?
O7 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
O7 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
O5 C1' O4 123.88(14) . . ?
O5 C1' C2' 124.31(14) . . ?
O4 C1' C2' 111.78(11) . . ?
C1' C2' C3' 108.63(10) . . ?
C1' C2' C4 112.68(10) . . ?
C3' C2' C4 113.39(11) . . ?
C1' C2' H2' 107.3 . . ?
C3' C2' H2' 107.3 . . ?
C4 C2' H2' 107.3 . . ?
O6 C3' C4' 122.37(14) . . ?
O6 C3' C2' 122.04(13) . . ?
C4' C3' C2' 115.57(14) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.30(10) . . ?
C9 O3 C10 116.30(11) . . ?
C1' O4 C5' 116.54(12) . . ?
C6 O7 C12 117.84(19) . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 952577'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd3
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Br O6'
_chemical_formula_sum            'C17 H17 Br O6'

_chemical_formula_weight         397.21

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'
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                   8.5665(3)
_cell_length_b                   9.1041(3)
_cell_length_c                   12.5319(4)
_cell_angle_alpha                77.751(2)
_cell_angle_beta                 74.492(2)
_cell_angle_gamma                66.840(2)
_cell_volume                     859.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.420
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_T_max  0.616
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8378
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.891
_diffrn_reflns_theta_max         30.639
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5224
_reflns_number_gt                2920
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0570P)²+0.1340P] 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         5224
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
C2 C 0.2678(3) 0.4248(3) 0.99227(18) 0.0447(5) Uani 1 1 d . . . . .
C3 C 0.2489(3) 0.3035(3) 0.95876(17) 0.0411(5) Uani 1 1 d . . . . .
C4 C 0.2034(3) 0.3154(2) 0.84868(17) 0.0401(5) Uani 1 1 d . . . . .
H4 H 0.1045 0.2801 0.8640 0.048 Uiso 1 1 calc R U . . .
C4A C 0.1451(3) 0.4887(2) 0.79504(18) 0.0423(5) Uani 1 1 d . . . . .
C5 C 0.0708(3) 0.5347(3) 0.70165(19) 0.0497(5) Uani 1 1 d . . . . .
H5 H 0.0537 0.4588 0.6713 0.060 Uiso 1 1 calc R U . . .
C6 C 0.0226(3) 0.6924(3) 0.6540(2) 0.0568(6) Uani 1 1 d . . . . .
C7 C 0.0481(4) 0.8076(3) 0.6959(2) 0.0652(7) Uani 1 1 d . . . . .
H7 H 0.0167 0.9135 0.6620 0.078 Uiso 1 1 calc R U . . .
C8 C 0.1202(4) 0.7637(3) 0.7881(2) 0.0602(6) Uani 1 1 d . . . . .
H8 H 0.1371 0.8403 0.8179 0.072 Uiso 1 1 calc R U . . .
C8A C 0.1683(3) 0.6052(3) 0.83739(19) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.2768(3) 0.1481(3) 1.03126(18) 0.0434(5) Uani 1 1 d . . . . .
C10 C 0.2280(4) -0.0976(3) 1.0633(2) 0.0632(7) Uani 1 1 d . . . . .
H101 H 0.1715 -0.1499 1.0356 0.095 Uiso 1 1 calc R U . . .
H102 H 0.1774 -0.0860 1.1407 0.095 Uiso 1 1 calc R U . . .
H103 H 0.3493 -0.1612 1.0553 0.095 Uiso 1 1 calc R U . . .
C11 C 0.3178(4) 0.4291(3) 1.0960(2) 0.0576(6) Uani 1 1 d . . . . .
H111 H 0.4411 0.4021 1.0825 0.086 Uiso 1 1 calc R U . . .
H112 H 0.2847 0.3529 1.1541 0.086 Uiso 1 1 calc R U . . .
H113 H 0.2600 0.5352 1.1185 0.086 Uiso 1 1 calc R U . . .
C1' C 0.4572(3) 0.2863(3) 0.6816(2) 0.0506(5) Uani 1 1 d . . . . .
C2' C 0.3555(3) 0.1991(2) 0.77143(17) 0.0430(5) Uani 1 1 d . . . . .
H2' H 0.4354 0.1232 0.8182 0.052 Uiso 1 1 calc R U . . .
C3' C 0.2966(4) 0.1000(3) 0.7168(2) 0.0544(6) Uani 1 1 d . . . . .
C4' C 0.4370(5) -0.0421(4) 0.6674(3) 0.0810(9) Uani 1 1 d . . . . .
H4'1 H 0.4744 -0.1260 0.7261 0.122 Uiso 1 1 calc R U . . .
H4'2 H 0.5331 -0.0116 0.6248 0.122 Uiso 1 1 calc R U . . .
H4'3 H 0.3939 -0.0801 0.6197 0.122 Uiso 1 1 calc R U . . .
C5' C 0.6183(5) 0.4566(5) 0.6487(3) 0.0957(12) Uani 1 1 d . . . . .
H5'1 H 0.7129 0.3930 0.5970 0.144 Uiso 1 1 calc R U . . .
H5'2 H 0.6616 0.5050 0.6896 0.144 Uiso 1 1 calc R U . . .
H5'3 H 0.5367 0.5393 0.6086 0.144 Uiso 1 1 calc R U . . .
O1 O 0.2380(2) 0.57312(19) 0.93043(14) 0.0543(4) Uani 1 1 d . . . . .
O2 O 0.3530(2) 0.1012(2) 1.10715(14) 0.0599(4) Uani 1 1 d . . . . .
O3 O 0.2062(2) 0.05937(18) 1.00064(13) 0.0526(4) Uani 1 1 d . . . . .
O4 O 0.5332(2) 0.3544(2) 0.72566(14) 0.0607(5) Uani 1 1 d . . . . .
O5 O 0.4658(3) 0.2955(3) 0.58379(16) 0.0815(6) Uani 1 1 d . . . . .
O6 O 0.1464(3) 0.1324(2) 0.71855(17) 0.0690(5) Uani 1 1 d . . . . .
Br1 Br -0.07911(4) 0.75336(4) 0.52692(3) 0.08619(16) 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
C2 C3 1.340(3) . ?
C2 O1 1.371(3) . ?
C2 C11 1.486(3) . ?
C3 C9 1.480(3) . ?
C3 C4 1.502(3) . ?
C4 C4A 1.517(3) . ?
C4 C2' 1.559(3) . ?
C4 H4 0.9800 . ?
C4A C8A 1.380(3) . ?
C4A C5 1.390(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 Br1 1.895(3) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.387(3) . ?
C8 H8 0.9300 . ?
C8A O1 1.375(3) . ?
C9 O2 1.206(3) . ?
C9 O3 1.343(3) . ?
C10 O3 1.444(3) . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?
C11 H111 0.9600 . ?
C11 H112 0.9600 . ?
C11 H113 0.9600 . ?
C1' O5 1.194(3) . ?
C1' O4 1.331(3) . ?
C1' C2' 1.515(3) . ?
C2' C3' 1.531(3) . ?
C2' H2' 0.9800 . ?
C3' O6 1.196(3) . ?
C3' C4' 1.490(4) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.450(3) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 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
C3 C2 O1 122.1(2) . . ?
C3 C2 C11 129.3(2) . . ?
O1 C2 C11 108.7(2) . . ?
C2 C3 C9 119.5(2) . . ?
C2 C3 C4 123.21(18) . . ?
C9 C3 C4 117.32(19) . . ?
C3 C4 C4A 110.71(18) . . ?
C3 C4 C2' 111.00(16) . . ?
C4A C4 C2' 113.21(17) . . ?
C3 C4 H4 107.2 . . ?
C4A C4 H4 107.2 . . ?
C2' C4 H4 107.2 . . ?
C8A C4A C5 118.15(19) . . ?
C8A C4A C4 120.16(19) . . ?
C5 C4A C4 121.7(2) . . ?
C6 C5 C4A 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4A C5 H5 120.0 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 Br1 119.5(2) . . ?
C7 C6 Br1 118.95(18) . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C8A 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
O1 C8A C4A 122.86(19) . . ?
O1 C8A C8 115.9(2) . . ?
C4A C8A C8 121.3(2) . . ?
O2 C9 O3 122.5(2) . . ?
O2 C9 C3 126.9(2) . . ?
O3 C9 C3 110.57(18) . . ?
O3 C10 H101 109.5 . . ?
O3 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
O3 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
O5 C1' O4 124.1(2) . . ?
O5 C1' C2' 124.6(2) . . ?
O4 C1' C2' 111.23(19) . . ?
C1' C2' C3' 109.08(19) . . ?
C1' C2' C4 112.41(17) . . ?
C3' C2' C4 113.20(19) . . ?
C1' C2' H2' 107.3 . . ?
C3' C2' H2' 107.3 . . ?
C4 C2' H2' 107.3 . . ?
O6 C3' C4' 123.1(3) . . ?
O6 C3' C2' 121.3(2) . . ?
C4' C3' C2' 115.5(3) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.37(17) . . ?
C9 O3 C10 116.21(19) . . ?
C1' O4 C5' 116.4(2) . . ?

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 C9 -177.76(19) . . . . ?
C11 C2 C3 C9 1.0(4) . . . . ?
O1 C2 C3 C4 3.5(3) . . . . ?
C11 C2 C3 C4 -177.7(2) . . . . ?
C2 C3 C4 C4A -12.3(3) . . . . ?
C9 C3 C4 C4A 168.96(18) . . . . ?
C2 C3 C4 C2' 114.3(2) . . . . ?
C9 C3 C4 C2' -64.4(2) . . . . ?
C3 C4 C4A C8A 11.4(3) . . . . ?
C2' C4 C4A C8A -114.0(2) . . . . ?
C3 C4 C4A C5 -169.85(19) . . . . ?
C2' C4 C4A C5 64.8(3) . . . . ?
C8A C4A C5 C6 0.0(3) . . . . ?
C4 C4A C5 C6 -178.8(2) . . . . ?
C4A C5 C6 C7 0.8(4) . . . . ?
C4A C5 C6 Br1 -179.84(16) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
Br1 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C8A 0.7(4) . . . . ?
C5 C4A C8A O1 178.9(2) . . . . ?
C4 C4A C8A O1 -2.3(3) . . . . ?
C5 C4A C8A C8 -0.4(3) . . . . ?
C4 C4A C8A C8 178.3(2) . . . . ?
C7 C8 C8A O1 -179.3(2) . . . . ?
C7 C8 C8A C4A 0.1(4) . . . . ?
C2 C3 C9 O2 -18.3(4) . . . . ?
C4 C3 C9 O2 160.5(2) . . . . ?
C2 C3 C9 O3 162.62(19) . . . . ?
C4 C3 C9 O3 -18.6(3) . . . . ?
O5 C1' C2' C3' 10.7(3) . . . . ?
O4 C1' C2' C3' -170.57(19) . . . . ?
O5 C1' C2' C4 -115.7(3) . . . . ?
O4 C1' C2' C4 63.0(2) . . . . ?
C3 C4 C2' C1' -103.0(2) . . . . ?
C4A C4 C2' C1' 22.2(3) . . . . ?
C3 C4 C2' C3' 132.82(18) . . . . ?
C4A C4 C2' C3' -102.0(2) . . . . ?
C1' C2' C3' O6 -113.2(2) . . . . ?
C4 C2' C3' O6 12.7(3) . . . . ?
C1' C2' C3' C4' 69.7(3) . . . . ?
C4 C2' C3' C4' -164.3(2) . . . . ?
C3 C2 O1 C8A 7.3(3) . . . . ?
C11 C2 O1 C8A -171.69(19) . . . . ?
C4A C8A O1 C2 -7.8(3) . . . . ?
C8 C8A O1 C2 171.6(2) . . . . ?
O2 C9 O3 C10 -0.6(3) . . . . ?
C3 C9 O3 C10 178.6(2) . . . . ?
O5 C1' O4 C5' 5.4(4) . . . . ?
C2' C1' O4 C5' -173.3(2) . . . . ?

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
C5' H5'3 O5 0.96 2.56 3.341(4) 138.8 2_666
C5' H5'1 Br1 0.96 3.00 3.910(4) 158.2 2_666
C4' H4'2 O5 0.96 2.59 3.114(4) 114.8 .
C2' H2' O2 0.98 2.35 3.305(3) 164.9 2_657
C11 H112 O2 0.96 2.30 2.856(3) 116.5 .

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 952578'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cpd4
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl O6'
_chemical_formula_sum            'C17 H17 Cl O6'

_chemical_formula_weight         352.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.4753(3)
_cell_length_b                   9.1065(3)
_cell_length_c                   12.4545(4)
_cell_angle_alpha                78.551(2)
_cell_angle_beta                 75.245(2)
_cell_angle_gamma                66.078(2)
_cell_volume                     844.75(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8270
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.403
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5120
_reflns_number_gt                3500
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0794P)²+0.1114P] 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         5120
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C2 C 0.76685(19) 0.42721(18) 0.48826(12) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.74742(18) 0.30530(17) 0.45550(11) 0.0367(3) Uani 1 1 d . . . . .
C4 C 0.70131(18) 0.31512(16) 0.34414(11) 0.0360(3) Uani 1 1 d . . . . .
H4 H 0.6013 0.2811 0.3587 0.043 Uiso 1 1 calc R U . . .
C4A C 0.64207(18) 0.48756(17) 0.29021(12) 0.0385(3) Uani 1 1 d . . . . .
C5 C 0.5654(2) 0.53187(19) 0.19624(13) 0.0469(4) Uani 1 1 d . . . . .
H5 H 0.5472 0.4554 0.1664 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5162(2) 0.6905(2) 0.14737(14) 0.0563(5) Uani 1 1 d . . . . .
C7 C 0.5431(3) 0.8059(2) 0.18908(16) 0.0645(5) Uani 1 1 d . . . . .
H7 H 0.5111 0.9114 0.1547 0.077 Uiso 1 1 calc R U . . .
C8 C 0.6175(3) 0.7635(2) 0.28158(16) 0.0573(4) Uani 1 1 d . . . . .
H8 H 0.6357 0.8404 0.3109 0.069 Uiso 1 1 calc R U . . .
C8A C 0.6657(2) 0.60508(18) 0.33149(13) 0.0428(3) Uani 1 1 d . . . . .
C9 C 0.77501(19) 0.15149(18) 0.52852(12) 0.0395(3) Uani 1 1 d . . . . .
C10 C 0.7265(3) -0.0933(2) 0.56071(17) 0.0593(5) Uani 1 1 d . . . . .
H103 H 0.8494 -0.1602 0.5506 0.089 Uiso 1 1 calc R U . . .
H102 H 0.6648 -0.1436 0.5351 0.089 Uiso 1 1 calc R U . . .
H101 H 0.6803 -0.0798 0.6385 0.089 Uiso 1 1 calc R U . . .
C11 C 0.8172(2) 0.4336(2) 0.59321(14) 0.0532(4) Uani 1 1 d . . . . .
H113 H 0.7743 0.3664 0.6530 0.080 Uiso 1 1 calc R U . . .
H112 H 0.7666 0.5430 0.6115 0.080 Uiso 1 1 calc R U . . .
H111 H 0.9430 0.3954 0.5827 0.080 Uiso 1 1 calc R U . . .
C1' C 0.9595(2) 0.27831(19) 0.17872(13) 0.0460(4) Uani 1 1 d . . . . .
C2' C 0.85683(19) 0.19506(17) 0.26761(12) 0.0398(3) Uani 1 1 d . . . . .
H2' H 0.9378 0.1195 0.3153 0.048 Uiso 1 1 calc R U . . .
C3' C 0.7968(3) 0.09466(19) 0.21355(13) 0.0509(4) Uani 1 1 d . . . . .
C4' C 0.9400(3) -0.0503(3) 0.16412(19) 0.0777(6) Uani 1 1 d . . . . .
H4'1 H 0.9700 -0.1378 0.2221 0.117 Uiso 1 1 calc R U . . .
H4'2 H 1.0417 -0.0246 0.1287 0.117 Uiso 1 1 calc R U . . .
H4'3 H 0.9003 -0.0816 0.1099 0.117 Uiso 1 1 calc R U . . .
C5' C 1.1265(4) 0.4422(4) 0.1472(2) 0.0954(9) Uani 1 1 d . . . . .
H5'1 H 1.0437 0.5287 0.1083 0.143 Uiso 1 1 calc R U . . .
H5'2 H 1.2187 0.3759 0.0944 0.143 Uiso 1 1 calc R U . . .
H5'3 H 1.1760 0.4861 0.1882 0.143 Uiso 1 1 calc R U . . .
O1 O 0.73776(17) 0.57433(13) 0.42527(10) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.85203(17) 0.10569(15) 0.60569(10) 0.0557(3) Uani 1 1 d . . . . .
O3 O 0.70372(15) 0.06275(13) 0.49748(9) 0.0484(3) Uani 1 1 d . . . . .
O4 O 1.03786(16) 0.34544(17) 0.22384(10) 0.0577(3) Uani 1 1 d . . . . .
O5 O 0.9672(2) 0.2872(2) 0.08052(11) 0.0760(4) Uani 1 1 d . . . . .
O6 O 0.6435(2) 0.12798(16) 0.21538(12) 0.0665(4) Uani 1 1 d . . . . .
Cl1 Cl 0.41850(8) 0.74407(7) 0.03139(5) 0.0874(2) 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
C2 C3 1.337(2) . ?
C2 O1 1.3728(18) . ?
C2 C11 1.493(2) . ?
C3 C9 1.4767(19) . ?
C3 C4 1.5109(19) . ?
C4 C4A 1.5109(18) . ?
C4 C2' 1.564(2) . ?
C4 H4 0.9800 . ?
C4A C8A 1.376(2) . ?
C4A C5 1.394(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 Cl1 1.7356(18) . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C8A 1.390(2) . ?
C8 H8 0.9300 . ?
C8A O1 1.382(2) . ?
C9 O2 1.2097(18) . ?
C9 O3 1.3441(19) . ?
C10 O3 1.4449(19) . ?
C10 H103 0.9600 . ?
C10 H102 0.9600 . ?
C10 H101 0.9600 . ?
C11 H113 0.9600 . ?
C11 H112 0.9600 . ?
C11 H111 0.9600 . ?
C1' O5 1.196(2) . ?
C1' O4 1.336(2) . ?
C1' C2' 1.506(2) . ?
C2' C3' 1.531(2) . ?
C2' H2' 0.9800 . ?
C3' O6 1.204(2) . ?
C3' C4' 1.496(3) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.445(2) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 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
C3 C2 O1 122.35(13) . . ?
C3 C2 C11 128.98(14) . . ?
O1 C2 C11 108.66(14) . . ?
C2 C3 C9 119.90(13) . . ?
C2 C3 C4 122.91(12) . . ?
C9 C3 C4 117.17(13) . . ?
C4A C4 C3 110.55(12) . . ?
C4A C4 C2' 113.21(11) . . ?
C3 C4 C2' 110.91(11) . . ?
C4A C4 H4 107.3 . . ?
C3 C4 H4 107.3 . . ?
C2' C4 H4 107.3 . . ?
C8A C4A C5 118.04(13) . . ?
C8A C4A C4 120.70(13) . . ?
C5 C4A C4 121.24(14) . . ?
C6 C5 C4A 119.71(17) . . ?
C6 C5 H5 120.1 . . ?
C4A C5 H5 120.1 . . ?
C7 C6 C5 121.37(16) . . ?
C7 C6 Cl1 119.53(13) . . ?
C5 C6 Cl1 119.10(16) . . ?
C8 C7 C6 119.26(16) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C8A 119.64(18) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 H8 120.2 . . ?
C4A C8A O1 122.58(13) . . ?
C4A C8A C8 121.97(16) . . ?
O1 C8A C8 115.44(15) . . ?
O2 C9 O3 122.56(14) . . ?
O2 C9 C3 126.66(15) . . ?
O3 C9 C3 110.78(12) . . ?
O3 C10 H103 109.5 . . ?
O3 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
O3 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
H102 C10 H101 109.5 . . ?
C2 C11 H113 109.5 . . ?
C2 C11 H112 109.5 . . ?
H113 C11 H112 109.5 . . ?
C2 C11 H111 109.5 . . ?
H113 C11 H111 109.5 . . ?
H112 C11 H111 109.5 . . ?
O5 C1' O4 124.00(16) . . ?
O5 C1' C2' 124.82(16) . . ?
O4 C1' C2' 111.16(13) . . ?
C1' C2' C3' 109.67(13) . . ?
C1' C2' C4 112.64(12) . . ?
C3' C2' C4 112.69(13) . . ?
C1' C2' H2' 107.2 . . ?
C3' C2' H2' 107.2 . . ?
C4 C2' H2' 107.2 . . ?
O6 C3' C4' 122.96(18) . . ?
O6 C3' C2' 121.50(16) . . ?
C4' C3' C2' 115.48(17) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.12(12) . . ?
C9 O3 C10 116.12(13) . . ?
C1' O4 C5' 116.22(16) . . ?

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 C9 -178.02(13) . . . . ?
C11 C2 C3 C9 0.8(2) . . . . ?
O1 C2 C3 C4 3.3(2) . . . . ?
C11 C2 C3 C4 -177.90(15) . . . . ?
C2 C3 C4 C4A -12.65(19) . . . . ?
C9 C3 C4 C4A 168.64(12) . . . . ?
C2 C3 C4 C2' 113.77(15) . . . . ?
C9 C3 C4 C2' -64.93(16) . . . . ?
C3 C4 C4A C8A 11.95(19) . . . . ?
C2' C4 C4A C8A -113.18(15) . . . . ?
C3 C4 C4A C5 -169.34(13) . . . . ?
C2' C4 C4A C5 65.53(18) . . . . ?
C8A C4A C5 C6 0.2(2) . . . . ?
C4 C4A C5 C6 -178.53(14) . . . . ?
C4A C5 C6 C7 0.7(3) . . . . ?
C4A C5 C6 Cl1 -179.25(12) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
Cl1 C6 C7 C8 178.92(14) . . . . ?
C6 C7 C8 C8A 0.4(3) . . . . ?
C5 C4A C8A O1 178.89(14) . . . . ?
C4 C4A C8A O1 -2.4(2) . . . . ?
C5 C4A C8A C8 -0.8(2) . . . . ?
C4 C4A C8A C8 177.99(14) . . . . ?
C7 C8 C8A C4A 0.4(3) . . . . ?
C7 C8 C8A O1 -179.23(16) . . . . ?
C2 C3 C9 O2 -18.0(2) . . . . ?
C4 C3 C9 O2 160.77(15) . . . . ?
C2 C3 C9 O3 162.85(13) . . . . ?
C4 C3 C9 O3 -18.40(18) . . . . ?
O5 C1' C2' C3' 11.8(2) . . . . ?
O4 C1' C2' C3' -169.94(14) . . . . ?
O5 C1' C2' C4 -114.58(19) . . . . ?
O4 C1' C2' C4 63.70(17) . . . . ?
C4A C4 C2' C1' 22.09(17) . . . . ?
C3 C4 C2' C1' -102.84(14) . . . . ?
C4A C4 C2' C3' -102.63(14) . . . . ?
C3 C4 C2' C3' 132.43(12) . . . . ?
C1' C2' C3' O6 -113.98(18) . . . . ?
C4 C2' C3' O6 12.4(2) . . . . ?
C1' C2' C3' C4' 68.90(18) . . . . ?
C4 C2' C3' C4' -164.77(15) . . . . ?
C3 C2 O1 C8A 8.0(2) . . . . ?
C11 C2 O1 C8A -171.02(13) . . . . ?
C4A C8A O1 C2 -8.4(2) . . . . ?
C8 C8A O1 C2 171.26(14) . . . . ?
O2 C9 O3 C10 -1.0(2) . . . . ?
C3 C9 O3 C10 178.26(14) . . . . ?
O5 C1' O4 C5' 4.0(3) . . . . ?
C2' C1' O4 C5' -174.25(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
C5' H5'2 Cl1 0.96 2.93 3.811(3) 152.5 2_765
C5' H5'1 O5 0.96 2.60 3.396(3) 140.3 2_765
C4' H4'2 O5 0.96 2.62 3.125(3) 112.9 .
C2' H2' O2 0.98 2.34 3.2965(17) 165.1 2_756
C11 H113 O2 0.96 2.35 2.855(2) 112.5 .

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 952579'
