# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 976243'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl2 O4'
_chemical_formula_sum            'C16 H16 Cl2 O4'
_chemical_formula_weight         343.19

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      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                   6.8501(5)
_cell_length_b                   22.1100(15)
_cell_length_c                   9.8260(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.315(2)
_cell_angle_gamma                90
_cell_volume                     1468.58(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3369
_cell_measurement_theta_min      2.294
_cell_measurement_theta_max      27.499

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.458
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15996
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         27.499
_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             3369
_reflns_number_gt                2918
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0425P)²+0.5884P] 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         3369
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5441(2) 0.10954(6) 0.80439(14) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.5729(2) 0.12583(7) 0.95523(15) 0.0338(3) Uani 1 1 d . . . . .
H2 H 0.465571 0.138375 0.995227 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7510(2) 0.12227(7) 1.03077(15) 0.0358(3) Uani 1 1 d . . . . .
C4 C 0.9329(2) 0.10831(7) 0.97034(16) 0.0338(3) Uani 1 1 d . . . . .
C5 C 0.9019(2) 0.09096(7) 0.81863(15) 0.0299(3) Uani 1 1 d . . . . .
H5 H 1.021611 0.100753 0.780325 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8558(2) 0.02292(7) 0.79727(17) 0.0344(3) Uani 1 1 d . . . . .
H6 H 0.966551 -0.001021 0.845041 0.041 Uiso 1 1 calc R U . . .
C7 C 0.8256(2) 0.00895(7) 0.64570(17) 0.0390(4) Uani 1 1 d . . . . .
H7 H 0.865945 -0.028418 0.616813 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7437(2) 0.04804(7) 0.55254(17) 0.0359(3) Uani 1 1 d . . . . .
H8 H 0.715142 0.034902 0.461576 0.043 Uiso 1 1 calc R U . . .
C9 C 0.6927(2) 0.11258(6) 0.58239(14) 0.0278(3) Uani 1 1 d . . . . .
H9 H 0.788191 0.137853 0.544184 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7268(2) 0.12522(6) 0.73838(14) 0.0252(3) Uani 1 1 d . . . . .
C11 C 0.6672(2) 0.00699(7) 0.85387(17) 0.0372(3) Uani 1 1 d . . . . .
H11A H 0.632546 -0.034900 0.832863 0.045 Uiso 1 1 calc R U . . .
H11B H 0.689893 0.011702 0.953326 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3231(2) 0.11715(7) 0.59340(15) 0.0296(3) Uani 1 1 d . . . . .
H12 H 0.309044 0.073042 0.593794 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4856(2) 0.13291(7) 0.50934(15) 0.0299(3) Uani 1 1 d . . . . .
H13 H 0.457480 0.109024 0.424410 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4780(2) 0.19918(8) 0.46430(17) 0.0387(4) Uani 1 1 d . . . . .
H14A H 0.526687 0.224575 0.542998 0.046 Uiso 1 1 calc R U . . .
H14B H 0.563274 0.205018 0.395624 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2679(3) 0.21794(8) 0.40433(18) 0.0433(4) Uani 1 1 d . . . . .
H15A H 0.264024 0.260671 0.381727 0.052 Uiso 1 1 calc R U . . .
H15B H 0.222101 0.195280 0.320725 0.052 Uiso 1 1 calc R U . . .
C16 C 0.1378(3) 0.20522(8) 0.51032(19) 0.0445(4) Uani 1 1 d . . . . .
H16A H 0.184373 0.228187 0.593354 0.053 Uiso 1 1 calc R U . . .
H16B H 0.003604 0.217968 0.475263 0.053 Uiso 1 1 calc R U . . .
O1 O 1.09591(18) 0.10899(6) 1.03963(13) 0.0495(3) Uani 1 1 d . . . . .
O2 O 0.37407(14) 0.13735(4) 0.73615(10) 0.0292(2) Uani 1 1 d . . . . .
O3 O 0.13919(15) 0.14186(5) 0.54284(12) 0.0389(3) Uani 1 1 d . . . . .
O4 O 0.50719(15) 0.04545(5) 0.79430(11) 0.0331(2) Uani 1 1 d . . . . .
CL1 Cl 0.78905(8) 0.13312(3) 1.20754(4) 0.05763(16) Uani 1 1 d . . . . .
CL2 Cl 0.78019(6) 0.20518(2) 0.76522(4) 0.03513(11) 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 O2 1.3898(17) . ?
C1 O4 1.4399(17) . ?
C1 C2 1.507(2) . ?
C1 C10 1.5397(18) . ?
C2 C3 1.324(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.496(2) . ?
C3 CL1 1.7309(15) . ?
C4 O1 1.2103(19) . ?
C4 C5 1.521(2) . ?
C5 C10 1.5258(19) . ?
C5 C6 1.545(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.502(2) . ?
C6 C11 1.528(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.317(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.509(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.5382(19) . ?
C9 C13 1.549(2) . ?
C9 H9 0.9800 . ?
C10 CL2 1.8159(14) . ?
C11 O4 1.4350(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O3 1.3890(18) . ?
C12 O2 1.4596(17) . ?
C12 C13 1.5300(19) . ?
C12 H12 0.9800 . ?
C13 C14 1.529(2) . ?
C13 H13 0.9800 . ?
C14 C15 1.522(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.503(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.437(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 O4 106.14(11) . . ?
O2 C1 C2 109.55(11) . . ?
O4 C1 C2 107.25(11) . . ?
O2 C1 C10 111.85(11) . . ?
O4 C1 C10 109.78(11) . . ?
C2 C1 C10 112.01(12) . . ?
C3 C2 C1 119.93(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 122.74(14) . . ?
C2 C3 CL1 121.99(12) . . ?
C4 C3 CL1 115.27(12) . . ?
O1 C4 C3 121.73(15) . . ?
O1 C4 C5 121.60(14) . . ?
C3 C4 C5 116.63(13) . . ?
C4 C5 C10 110.77(11) . . ?
C4 C5 C6 111.83(12) . . ?
C10 C5 C6 106.68(12) . . ?
C4 C5 H5 109.2 . . ?
C10 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C7 C6 C11 108.93(13) . . ?
C7 C6 C5 109.11(13) . . ?
C11 C6 C5 109.96(12) . . ?
C7 C6 H6 109.6 . . ?
C11 C6 H6 109.6 . . ?
C5 C6 H6 109.6 . . ?
C8 C7 C6 121.95(14) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 124.86(14) . . ?
C7 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C8 C9 C10 111.28(12) . . ?
C8 C9 C13 114.05(12) . . ?
C10 C9 C13 112.89(11) . . ?
C8 C9 H9 106.0 . . ?
C10 C9 H9 106.0 . . ?
C13 C9 H9 106.0 . . ?
C5 C10 C9 113.87(11) . . ?
C5 C10 C1 107.16(11) . . ?
C9 C10 C1 112.09(11) . . ?
C5 C10 CL2 106.58(9) . . ?
C9 C10 CL2 108.44(9) . . ?
C1 C10 CL2 108.44(9) . . ?
O4 C11 C6 110.49(12) . . ?
O4 C11 H11A 109.6 . . ?
C6 C11 H11A 109.6 . . ?
O4 C11 H11B 109.6 . . ?
C6 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O3 C12 O2 106.59(11) . . ?
O3 C12 C13 114.47(12) . . ?
O2 C12 C13 111.54(11) . . ?
O3 C12 H12 108.0 . . ?
O2 C12 H12 108.0 . . ?
C13 C12 H12 108.0 . . ?
C14 C13 C12 112.39(12) . . ?
C14 C13 C9 113.44(12) . . ?
C12 C13 C9 112.06(12) . . ?
C14 C13 H13 106.1 . . ?
C12 C13 H13 106.1 . . ?
C9 C13 H13 106.1 . . ?
C15 C14 C13 111.04(13) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 108.08(13) . . ?
C16 C15 H15A 110.1 . . ?
C14 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C14 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
O3 C16 C15 110.69(14) . . ?
O3 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C1 O2 C12 112.32(10) . . ?
C12 O3 C16 115.85(12) . . ?
C11 O4 C1 116.17(11) . . ?

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 C3 -157.45(14) . . . . ?
O4 C1 C2 C3 87.77(17) . . . . ?
C10 C1 C2 C3 -32.7(2) . . . . ?
C1 C2 C3 C4 6.1(2) . . . . ?
C1 C2 C3 CL1 -173.49(11) . . . . ?
C2 C3 C4 O1 175.27(17) . . . . ?
CL1 C3 C4 O1 -5.1(2) . . . . ?
C2 C3 C4 C5 -6.9(2) . . . . ?
CL1 C3 C4 C5 172.74(11) . . . . ?
O1 C4 C5 C10 -147.99(15) . . . . ?
C3 C4 C5 C10 34.17(18) . . . . ?
O1 C4 C5 C6 93.15(18) . . . . ?
C3 C4 C5 C6 -84.69(16) . . . . ?
C4 C5 C6 C7 179.60(12) . . . . ?
C10 C5 C6 C7 58.35(15) . . . . ?
C4 C5 C6 C11 60.20(16) . . . . ?
C10 C5 C6 C11 -61.06(15) . . . . ?
C11 C6 C7 C8 85.88(19) . . . . ?
C5 C6 C7 C8 -34.2(2) . . . . ?
C6 C7 C8 C9 7.4(3) . . . . ?
C7 C8 C9 C10 -6.4(2) . . . . ?
C7 C8 C9 C13 -135.54(16) . . . . ?
C4 C5 C10 C9 176.97(11) . . . . ?
C6 C5 C10 C9 -61.10(15) . . . . ?
C4 C5 C10 C1 -58.48(15) . . . . ?
C6 C5 C10 C1 63.44(14) . . . . ?
C4 C5 C10 CL2 57.46(13) . . . . ?
C6 C5 C10 CL2 179.39(9) . . . . ?
C8 C9 C10 C5 34.39(16) . . . . ?
C13 C9 C10 C5 164.13(12) . . . . ?
C8 C9 C10 C1 -87.47(14) . . . . ?
C13 C9 C10 C1 42.27(16) . . . . ?
C8 C9 C10 CL2 152.85(10) . . . . ?
C13 C9 C10 CL2 -77.41(12) . . . . ?
O2 C1 C10 C5 -178.38(11) . . . . ?
O4 C1 C10 C5 -60.83(14) . . . . ?
C2 C1 C10 C5 58.20(15) . . . . ?
O2 C1 C10 C9 -52.76(15) . . . . ?
O4 C1 C10 C9 64.79(14) . . . . ?
C2 C1 C10 C9 -176.18(12) . . . . ?
O2 C1 C10 CL2 66.92(13) . . . . ?
O4 C1 C10 CL2 -175.53(9) . . . . ?
C2 C1 C10 CL2 -56.51(14) . . . . ?
C7 C6 C11 O4 -65.34(16) . . . . ?
C5 C6 C11 O4 54.18(17) . . . . ?
O3 C12 C13 C14 42.07(18) . . . . ?
O2 C12 C13 C14 -79.05(15) . . . . ?
O3 C12 C13 C9 171.21(12) . . . . ?
O2 C12 C13 C9 50.08(16) . . . . ?
C8 C9 C13 C14 -144.94(13) . . . . ?
C10 C9 C13 C14 86.75(15) . . . . ?
C8 C9 C13 C12 86.48(15) . . . . ?
C10 C9 C13 C12 -41.83(16) . . . . ?
C12 C13 C14 C15 -46.80(18) . . . . ?
C9 C13 C14 C15 -175.22(13) . . . . ?
C13 C14 C15 C16 56.09(19) . . . . ?
C14 C15 C16 O3 -60.85(19) . . . . ?
O4 C1 O2 C12 -56.93(13) . . . . ?
C2 C1 O2 C12 -172.41(11) . . . . ?
C10 C1 O2 C12 62.78(14) . . . . ?
O3 C12 O2 C1 172.43(10) . . . . ?
C13 C12 O2 C1 -61.96(15) . . . . ?
O2 C12 O3 C16 75.41(15) . . . . ?
C13 C12 O3 C16 -48.41(18) . . . . ?
C15 C16 O3 C12 58.67(19) . . . . ?
C6 C11 O4 C1 -53.05(17) . . . . ?
O2 C1 O4 C11 177.79(11) . . . . ?
C2 C1 O4 C11 -65.18(15) . . . . ?
C10 C1 O4 C11 56.74(15) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.049

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 976244'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Cl2 O4'
_chemical_formula_sum            'C16 H20 Cl2 O4'
_chemical_formula_weight         347.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   5.945(5)
_cell_length_b                   18.659(5)
_cell_length_c                   7.352(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.111(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     794.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1396
_cell_measurement_theta_min      2.183
_cell_measurement_theta_max      24.995

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.424
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6895
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.183
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_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             1396
_reflns_number_gt                1277
_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-2016/4 (Sheldrick, 2016)'
_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)+(0.0287P)²+0.2968P] 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         1396
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8915(2) 0.09488(8) 0.89227(19) 0.0345(3) Uani 1 1 d . . . . .
H1 H 1.024512 0.069162 0.866378 0.041 Uiso 1 1 calc R U . . .
C2 C 0.9700(3) 0.16708(9) 0.9762(2) 0.0426(4) Uani 1 1 d . . . . .
H2A H 1.026146 0.195717 0.885652 0.051 Uiso 1 1 calc R U . . .
H2B H 1.096248 0.160562 1.084517 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7733(3) 0.20612(8) 1.0336(2) 0.0477(4) Uani 1 1 d . . . . .
H3A H 0.830411 0.249851 1.099458 0.057 Uiso 1 1 calc R U . . .
H3B H 0.656304 0.218926 0.923503 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6687(3) 0.15817(9) 1.1592(2) 0.0477(4) Uani 1 1 d . . . . .
H4A H 0.780301 0.150157 1.275937 0.057 Uiso 1 1 calc R U . . .
H4B H 0.534375 0.181325 1.187113 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5992(3) 0.08737(9) 1.0637(2) 0.0461(4) Uani 1 1 d . . . . .
H5A H 0.541508 0.056063 1.148083 0.055 Uiso 1 1 calc R U . . .
H5B H 0.475144 0.095252 0.954563 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6223(2) 0.05373(7) 0.61515(18) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.3968(2) 0.06454(7) 0.51422(19) 0.0329(3) Uani 1 1 d . . . . .
C8 C 0.2753(3) 0.01192(8) 0.4003(2) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.78868(18) 0.05290(5) 1.00744(14) 0.0393(3) Uani 1 1 d . . . . .
O2 O 0.73052(17) 0.11021(5) 0.71836(13) 0.0367(3) Uani 1 1 d . . . . .
CL1 Cl 0.26467(7) 0.14651(2) 0.53181(6) 0.05208(16) Uani 1 1 d . . . . .
H8A H 0.126(3) 0.0217(9) 0.334(2) 0.045(5) 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
C1 O1 1.3923(18) . ?
C1 O2 1.4412(18) . ?
C1 C2 1.511(2) . ?
C1 H1 0.9800 . ?
C2 C3 1.517(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.516(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.509(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.437(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O2 1.3707(17) . ?
C6 C8 1.384(2) 3_656 ?
C6 C7 1.392(2) . ?
C7 C8 1.383(2) . ?
C7 CL1 1.7374(15) . ?
C8 C6 1.384(2) 3_656 ?
C8 H8A 0.929(17) . ?

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 110.89(12) . . ?
O1 C1 C2 113.01(13) . . ?
O2 C1 C2 105.48(12) . . ?
O1 C1 H1 109.1 . . ?
O2 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C1 C2 C3 110.82(13) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.55(14) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 109.87(14) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C5 C4 112.10(13) . . ?
O1 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
O1 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 C8 124.47(13) . 3_656 ?
O2 C6 C7 117.26(13) . . ?
C8 C6 C7 118.22(13) 3_656 . ?
C8 C7 C6 121.83(13) . . ?
C8 C7 CL1 119.17(12) . . ?
C6 C7 CL1 119.01(11) . . ?
C7 C8 C6 119.95(14) . 3_656 ?
C7 C8 H8A 118.8(10) . . ?
C6 C8 H8A 121.2(10) 3_656 . ?
C1 O1 C5 113.82(12) . . ?
C6 O2 C1 118.19(11) . . ?

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 C1 C2 C3 -53.61(17) . . . . ?
O2 C1 C2 C3 67.69(16) . . . . ?
C1 C2 C3 C4 53.19(17) . . . . ?
C2 C3 C4 C5 -54.33(18) . . . . ?
C3 C4 C5 O1 55.36(19) . . . . ?
O2 C6 C7 C8 177.58(13) . . . . ?
C8 C6 C7 C8 -0.2(2) 3_656 . . . ?
O2 C6 C7 CL1 -2.34(17) . . . . ?
C8 C6 C7 CL1 179.90(11) 3_656 . . . ?
C6 C7 C8 C6 0.2(2) . . . 3_656 ?
CL1 C7 C8 C6 -179.90(11) . . . 3_656 ?
O2 C1 O1 C5 -63.33(15) . . . . ?
C2 C1 O1 C5 54.85(16) . . . . ?
C4 C5 O1 C1 -56.08(18) . . . . ?
C8 C6 O2 C1 -36.25(19) 3_656 . . . ?
C7 C6 O2 C1 146.15(13) . . . . ?
O1 C1 O2 C6 -54.36(16) . . . . ?
C2 C1 O2 C6 -177.02(12) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1023672'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H32 O5'
_chemical_formula_sum            'C23 H32 O5'
_chemical_formula_weight         388.48

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.734(5)
_cell_length_b                   7.397(5)
_cell_length_c                   12.645(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 107.317(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1047.8(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4622
_cell_measurement_theta_min      1.687
_cell_measurement_theta_max      27.995

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9980
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.687
_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 0.912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4622
_reflns_number_gt                3363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.810
_reflns_Friedel_fraction_full    0.867

_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, 2008)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 2009)'
_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)+(0.1221P)²+0.0281P] 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 1105 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4622
_refine_ls_number_parameters     309
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1932
_refine_ls_wR_factor_gt          0.1732
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.064
_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 0.1594(4) 0.0133(8) 0.9664(4) 0.0734(12) Uani 1 1 d . . . . .
H1A H 0.113437 0.040122 1.015880 0.110 Uiso 1 1 calc R U . . .
H1B H 0.241756 -0.001494 1.008256 0.110 Uiso 1 1 calc R U . . .
H1C H 0.130394 -0.096289 0.926879 0.110 Uiso 1 1 calc R U . . .
C2 C 0.1478(3) 0.1654(6) 0.8858(3) 0.0558(9) Uani 1 1 d . . . . .
C3 C 0.0803(4) 0.3118(7) 0.8830(4) 0.0645(11) Uani 1 1 d . . . . .
H3 H 0.034677 0.317347 0.931734 0.077 Uiso 1 1 calc R U . . .
C4 C 0.0741(3) 0.4632(6) 0.8079(4) 0.0665(12) Uani 1 1 d . . . . .
C5 C 0.1426(3) 0.4518(5) 0.7212(3) 0.0540(9) Uani 1 1 d . . . . .
C6 C 0.0713(4) 0.5457(7) 0.6149(4) 0.0738(12) Uani 1 1 d . . . . .
H6A H 0.052706 0.666844 0.631495 0.111 Uiso 1 1 calc R U . . .
H6B H -0.001368 0.480360 0.582282 0.111 Uiso 1 1 calc R U . . .
H6C H 0.117646 0.549198 0.563852 0.111 Uiso 1 1 calc R U . . .
C7 C 0.1673(3) 0.2520(5) 0.6984(3) 0.0470(8) Uani 1 1 d . . . . .
H7 H 0.089445 0.196424 0.663062 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2198(3) 0.1534(5) 0.8068(3) 0.0471(8) Uani 1 1 d . . . . .
C9 C 0.2385(3) 0.2390(5) 0.6146(3) 0.0494(8) Uani 1 1 d . . . . .
H9 H 0.186564 0.285276 0.544061 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3453(3) 0.3617(5) 0.6484(3) 0.0507(8) Uani 1 1 d . . . . .
H10 H 0.408205 0.337633 0.619884 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3563(3) 0.5015(5) 0.7160(3) 0.0497(8) Uani 1 1 d . . . . .
C12 C 0.2608(3) 0.5525(5) 0.7691(3) 0.0490(8) Uani 1 1 d . . . . .
H12 H 0.245273 0.682429 0.758177 0.059 Uiso 1 1 calc R U . . .
C13 C 0.4096(4) 0.6267(7) 0.9356(3) 0.0632(10) Uani 1 1 d . . . . .
H13A H 0.436898 0.603264 1.014615 0.076 Uiso 1 1 calc R U . . .
H13B H 0.387988 0.753403 0.925095 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5109(4) 0.5891(6) 0.8870(3) 0.0597(9) Uani 1 1 d . . . . .
H14A H 0.540405 0.467226 0.906057 0.072 Uiso 1 1 calc R U . . .
H14B H 0.575934 0.672576 0.918269 0.072 Uiso 1 1 calc R U . . .
C15 C 0.4683(3) 0.6099(6) 0.7616(3) 0.0574(9) Uani 1 1 d . . . . .
H15A H 0.452759 0.736228 0.742198 0.069 Uiso 1 1 calc R U . . .
H15B H 0.529492 0.567469 0.730269 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2724(4) 0.0438(6) 0.5930(3) 0.0571(9) Uani 1 1 d . . . . .
H16A H 0.343832 0.009636 0.651162 0.069 Uiso 1 1 calc R U . . .
H16B H 0.208729 -0.036617 0.597553 0.069 Uiso 1 1 calc R U . . .
C17 C 0.2944(4) 0.0160(6) 0.4826(3) 0.0639(10) Uani 1 1 d . . . . .
H17A H 0.354872 0.100211 0.475012 0.077 Uiso 1 1 calc R U . . .
H17B H 0.221555 0.039294 0.423359 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3355(5) -0.1760(7) 0.4739(4) 0.0758(13) Uani 1 1 d . . . . .
H18A H 0.414486 -0.192055 0.525723 0.091 Uiso 1 1 calc R U . . .
H18B H 0.281843 -0.258895 0.494673 0.091 Uiso 1 1 calc R U . . .
O1 O 0.3110(2) 0.0657(4) 0.8306(2) 0.0597(7) Uani 1 1 d . . . . .
O2 O 0.0167(3) 0.5971(6) 0.8137(4) 0.0987(12) Uani 1 1 d . . . . .
O3 O 0.3060(2) 0.5186(4) 0.8862(2) 0.0559(7) Uani 1 1 d . . . . .
O4 O 0.3393(3) -0.2199(5) 0.3655(3) 0.0794(10) Uani 1 1 d D . . . .
O5 O 0.3676(9) -0.4058(19) 0.2261(7) 0.116(3) Uani 0.5 1 d D U P A 1
C19 C 0.3631(9) -0.3890(12) 0.3427(7) 0.074(2) Uani 0.5 1 d D U P A 1
H19 H 0.444680 -0.412713 0.389536 0.089 Uiso 0.5 1 calc R U P A 1
C20 C 0.2923(9) -0.5177(11) 0.3730(6) 0.062(2) Uani 0.5 1 d D U P A 1
H20A H 0.293299 -0.498075 0.449073 0.074 Uiso 0.5 1 calc R U P A 1
H20B H 0.323418 -0.637741 0.367575 0.074 Uiso 0.5 1 calc R U P A 1
C21 C 0.1679(15) -0.504(4) 0.2984(12) 0.103(6) Uani 0.5 1 d D U P A 1
H21A H 0.138510 -0.381336 0.299418 0.123 Uiso 0.5 1 calc R U P A 1
H21B H 0.116188 -0.585077 0.323047 0.123 Uiso 0.5 1 calc R U P A 1
C22 C 0.1682(12) -0.553(3) 0.1842(12) 0.101(5) Uani 0.5 1 d D U P A 1
H22A H 0.087009 -0.551369 0.135105 0.121 Uiso 0.5 1 calc R U P A 1
H22B H 0.199652 -0.673841 0.184348 0.121 Uiso 0.5 1 calc R U P A 1
C23 C 0.2423(11) -0.423(3) 0.1428(9) 0.090(3) Uani 0.5 1 d D U P A 1
H23A H 0.203937 -0.305382 0.131517 0.108 Uiso 0.5 1 calc R U P A 1
H23B H 0.248997 -0.464624 0.072184 0.108 Uiso 0.5 1 calc R U P A 1
O5' O 0.2760(11) -0.3099(13) 0.1817(8) 0.104(3) Uani 0.5 1 d D U P A 2
C19' C 0.2429(7) -0.2400(13) 0.2808(6) 0.0647(19) Uani 0.5 1 d D U P A 2
H19' H 0.207262 -0.120083 0.261509 0.078 Uiso 0.5 1 calc R U P A 2
C20' C 0.1599(6) -0.3467(11) 0.3088(6) 0.0491(15) Uani 0.5 1 d D U P A 2
H20C H 0.084059 -0.335768 0.251441 0.059 Uiso 0.5 1 calc R U P A 2
H20D H 0.149061 -0.301295 0.377143 0.059 Uiso 0.5 1 calc R U P A 2
C21' C 0.1929(19) -0.5418(17) 0.3237(12) 0.070(4) Uani 0.5 1 d D U P A 2
H21C H 0.265129 -0.555860 0.385110 0.084 Uiso 0.5 1 calc R U P A 2
H21D H 0.129552 -0.608981 0.340737 0.084 Uiso 0.5 1 calc R U P A 2
C22' C 0.2122(13) -0.6139(17) 0.2216(12) 0.089(4) Uani 0.5 1 d D U P A 2
H22C H 0.235338 -0.739981 0.232833 0.107 Uiso 0.5 1 calc R U P A 2
H22D H 0.137956 -0.607606 0.161789 0.107 Uiso 0.5 1 calc R U P A 2
C23' C 0.3053(13) -0.5128(14) 0.1899(12) 0.079(3) Uani 0.5 1 d D U P A 2
H23C H 0.310182 -0.556362 0.118987 0.095 Uiso 0.5 1 calc R U P A 2
H23D H 0.382077 -0.532497 0.244592 0.095 Uiso 0.5 1 calc R U P A 2


_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 C2 1.498(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.336(6) . ?
C2 C8 1.490(5) . ?
C3 C4 1.455(7) . ?
C3 H3 0.9300 . ?
C4 O2 1.212(6) . ?
C4 C5 1.543(6) . ?
C5 C6 1.523(6) . ?
C5 C12 1.532(5) . ?
C5 C7 1.550(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.513(5) . ?
C7 C9 1.535(5) . ?
C7 H7 0.9800 . ?
C8 O1 1.211(4) . ?
C9 C10 1.503(5) . ?
C9 C16 1.544(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.323(5) . ?
C10 H10 0.9300 . ?
C11 C15 1.500(5) . ?
C11 C12 1.516(5) . ?
C12 O3 1.439(4) . ?
C12 H12 0.9800 . ?
C13 O3 1.433(5) . ?
C13 C14 1.517(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.521(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.507(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.515(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O4 1.421(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O4 C19' 1.315(8) . ?
O4 C19 1.332(9) . ?
O5a C19 1.495(11) . ?
O5a C23 1.537(11) . ?
C19a C20 1.391(11) . ?
C19a H19 0.9800 . ?
C20a C21 1.486(15) . ?
C20a H20A 0.9700 . ?
C20a H20B 0.9700 . ?
C21a C22 1.489(13) . ?
C21a H21A 0.9700 . ?
C21a H21B 0.9700 . ?
C22a C23 1.491(13) . ?
C22a H22A 0.9700 . ?
C22a H22B 0.9700 . ?
C23a H23A 0.9700 . ?
C23a H23B 0.9700 . ?
O5'b C19' 1.509(11) . ?
O5'b C23' 1.536(11) . ?
C19'b C20' 1.379(10) . ?
C19'b H19' 0.9800 . ?
C20'b C21' 1.491(14) . ?
C20'b H20C 0.9700 . ?
C20'b H20D 0.9700 . ?
C21'b C22' 1.475(12) . ?
C21'b H21C 0.9700 . ?
C21'b H21D 0.9700 . ?
C22'b C23' 1.475(12) . ?
C22'b H22C 0.9700 . ?
C22'b H22D 0.9700 . ?
C23'b H23C 0.9700 . ?
C23'b H23D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C8 118.7(4) . . ?
C3 C2 C1 124.1(4) . . ?
C8 C2 C1 117.2(4) . . ?
C2 C3 C4 123.7(3) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
O2 C4 C3 120.7(4) . . ?
O2 C4 C5 120.3(5) . . ?
C3 C4 C5 119.1(3) . . ?
C6 C5 C12 108.8(3) . . ?
C6 C5 C4 109.7(3) . . ?
C12 C5 C4 107.1(3) . . ?
C6 C5 C7 110.8(4) . . ?
C12 C5 C7 109.9(3) . . ?
C4 C5 C7 110.5(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C9 115.9(3) . . ?
C8 C7 C5 109.9(3) . . ?
C9 C7 C5 111.0(3) . . ?
C8 C7 H7 106.5 . . ?
C9 C7 H7 106.5 . . ?
C5 C7 H7 106.5 . . ?
O1 C8 C2 120.1(3) . . ?
O1 C8 C7 125.1(3) . . ?
C2 C8 C7 114.8(3) . . ?
C10 C9 C7 110.2(3) . . ?
C10 C9 C16 112.2(3) . . ?
C7 C9 C16 113.7(3) . . ?
C10 C9 H9 106.8 . . ?
C7 C9 H9 106.8 . . ?
C16 C9 H9 106.8 . . ?
C11 C10 C9 124.6(3) . . ?
C11 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
C10 C11 C15 124.9(3) . . ?
C10 C11 C12 122.6(3) . . ?
C15 C11 C12 112.0(3) . . ?
O3 C12 C11 108.5(3) . . ?
O3 C12 C5 109.6(3) . . ?
C11 C12 C5 113.9(3) . . ?
O3 C12 H12 108.2 . . ?
C11 C12 H12 108.2 . . ?
C5 C12 H12 108.2 . . ?
O3 C13 C14 112.7(3) . . ?
O3 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
O3 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 110.5(3) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C11 C15 C14 109.0(3) . . ?
C11 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
C11 C15 H15B 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C17 C16 C9 114.6(3) . . ?
C17 C16 H16A 108.6 . . ?
C9 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C9 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 110.0(4) . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O4 C18 C17 112.8(4) . . ?
O4 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
O4 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C13 O3 C12 110.9(3) . . ?
C19'b O4 C18 123.0(5) . . ?
C19a O4 C18 119.5(5) . . ?
C19a O5a C23 112.0(8) . . ?
O4 C19a C20 113.7(8) . . ?
O4 C19a O5 111.3(8) . . ?
C20a C19a O5 114.4(8) . . ?
O4 C19a H19 105.5 . . ?
C20a C19a H19 105.5 . . ?
O5a C19a H19 105.5 . . ?
C19a C20a C21 109.4(10) . . ?
C19a C20a H20A 109.8 . . ?
C21a C20a H20A 109.8 . . ?
C19a C20a H20B 109.8 . . ?
C21a C20a H20B 109.8 . . ?
H20Aa C20a H20B 108.2 . . ?
C20a C21a C22 108.2(13) . . ?
C20a C21a H21A 110.0 . . ?
C22a C21a H21A 110.1 . . ?
C20a C21a H21B 110.1 . . ?
C22a C21a H21B 110.0 . . ?
H21Aa C21a H21B 108.4 . . ?
C21a C22a C23 110.7(13) . . ?
C21a C22a H22A 109.5 . . ?
C23a C22a H22A 109.5 . . ?
C21a C22a H22B 109.5 . . ?
C23a C22a H22B 109.5 . . ?
H22Aa C22a H22B 108.1 . . ?
C22a C23a O5 110.6(12) . . ?
C22a C23a H23A 109.5 . . ?
O5a C23a H23A 109.5 . . ?
C22a C23a H23B 109.5 . . ?
O5a C23a H23B 109.5 . . ?
H23Aa C23a H23B 108.1 . . ?
C19'b O5'b C23' 112.8(8) . . ?
O4 C19'b C20' 110.9(7) . . ?
O4 C19'b O5' 110.1(7) . . ?
C20'b C19'b O5' 113.2(8) . . ?
O4 C19'b H19' 107.5 . . ?
C20'b C19'b H19' 107.5 . . ?
O5'b C19'b H19' 107.5 . . ?
C19'b C20'b C21' 114.2(10) . . ?
C19'b C20'b H20C 108.7 . . ?
C21'b C20'b H20C 108.7 . . ?
C19'b C20'b H20D 108.7 . . ?
C21'b C20'b H20D 108.7 . . ?
H20Cb C20'b H20D 107.6 . . ?
C22'b C21'b C20' 110.0(11) . . ?
C22'b C21'b H21C 109.7 . . ?
C20'b C21'b H21C 109.7 . . ?
C22'b C21'b H21D 109.7 . . ?
C20'b C21'b H21D 109.7 . . ?
H21Cb C21'b H21D 108.2 . . ?
C23'b C22'b C21' 112.0(11) . . ?
C23'b C22'b H22C 109.2 . . ?
C21'b C22'b H22C 109.2 . . ?
C23'b C22'b H22D 109.2 . . ?
C21'b C22'b H22D 109.2 . . ?
H22Cb C22'b H22D 107.9 . . ?
C22'b C23'b O5' 110.2(10) . . ?
C22'b C23'b H23C 109.6 . . ?
O5'b C23'b H23C 109.6 . . ?
C22'b C23'b H23D 109.6 . . ?
O5'b C23'b H23D 109.6 . . ?
H23Cb C23'b H23D 108.1 . . ?

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 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C4 176.8(4) . . . . ?
C2 C3 C4 O2 -175.6(4) . . . . ?
C2 C3 C4 C5 3.9(6) . . . . ?
O2 C4 C5 C6 -36.0(6) . . . . ?
C3 C4 C5 C6 144.5(4) . . . . ?
O2 C4 C5 C12 82.0(5) . . . . ?
C3 C4 C5 C12 -97.6(4) . . . . ?
O2 C4 C5 C7 -158.4(4) . . . . ?
C3 C4 C5 C7 22.1(5) . . . . ?
C6 C5 C7 C8 -170.7(3) . . . . ?
C12 C5 C7 C8 69.1(4) . . . . ?
C4 C5 C7 C8 -48.9(4) . . . . ?
C6 C5 C7 C9 59.8(4) . . . . ?
C12 C5 C7 C9 -60.5(4) . . . . ?
C4 C5 C7 C9 -178.4(3) . . . . ?
C3 C2 C8 O1 152.5(4) . . . . ?
C1 C2 C8 O1 -25.5(5) . . . . ?
C3 C2 C8 C7 -29.2(5) . . . . ?
C1 C2 C8 C7 152.8(4) . . . . ?
C9 C7 C8 O1 -0.8(5) . . . . ?
C5 C7 C8 O1 -127.6(4) . . . . ?
C9 C7 C8 C2 -178.9(3) . . . . ?
C5 C7 C8 C2 54.2(4) . . . . ?
C8 C7 C9 C10 -76.5(4) . . . . ?
C5 C7 C9 C10 49.8(4) . . . . ?
C8 C7 C9 C16 50.5(4) . . . . ?
C5 C7 C9 C16 176.8(3) . . . . ?
C7 C9 C10 C11 -20.8(5) . . . . ?
C16 C9 C10 C11 -148.6(4) . . . . ?
C9 C10 C11 C15 171.7(3) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 O3 111.4(4) . . . . ?
C15 C11 C12 O3 -60.4(4) . . . . ?
C10 C11 C12 C5 -11.0(5) . . . . ?
C15 C11 C12 C5 177.2(3) . . . . ?
C6 C5 C12 O3 156.4(3) . . . . ?
C4 C5 C12 O3 37.9(4) . . . . ?
C7 C5 C12 O3 -82.1(3) . . . . ?
C6 C5 C12 C11 -81.7(4) . . . . ?
C4 C5 C12 C11 159.7(3) . . . . ?
C7 C5 C12 C11 39.7(4) . . . . ?
O3 C13 C14 C15 54.2(5) . . . . ?
C10 C11 C15 C14 -116.5(4) . . . . ?
C12 C11 C15 C14 55.1(4) . . . . ?
C13 C14 C15 C11 -50.6(5) . . . . ?
C10 C9 C16 C17 -78.4(5) . . . . ?
C7 C9 C16 C17 155.7(3) . . . . ?
C9 C16 C17 C18 175.9(4) . . . . ?
C16 C17 C18 O4 170.4(4) . . . . ?
C14 C13 O3 C12 -60.2(4) . . . . ?
C11 C12 O3 C13 61.4(4) . . . . ?
C5 C12 O3 C13 -173.6(3) . . . . ?
C17 C18 O4 C19'b -70.3(7) . . . . ?
C17 C18 O4 C19a -173.8(6) . . . . ?
C18 O4 C19a C20a 51.2(9) . . . . ?
C18 O4 C19a O5a -177.8(6) . . . . ?
C23a O5a C19a O4 -81.4(14) . . . . ?
C23a O5a C19a C20a 49.2(16) . . . . ?
O4 C19a C20a C21a 70.3(12) . . . . ?
O5a C19a C20a C21a -59.1(13) . . . . ?
C19a C20a C21a C22a 65.0(18) . . . . ?
C20a C21a C22a C23a -63(2) . . . . ?
C21a C22a C23a O5a 52.6(19) . . . . ?
C19a O5a C23a C22a -44.4(19) . . . . ?
C18 O4 C19'b C20'b -46.5(9) . . . . ?
C18 O4 C19'b O5'b -172.5(6) . . . . ?
C23'b O5'b C19'b O4 76.8(13) . . . . ?
C23'b O5'b C19'b C20'b -48.0(14) . . . . ?
O4 C19'b C20'b C21'b -71.7(11) . . . . ?
O5'b C19'b C20'b C21'b 52.6(11) . . . . ?
C19'b C20'b C21'b C22'b -57.4(17) . . . . ?
C20'b C21'b C22'b C23'b 57.6(19) . . . . ?
C21'b C22'b C23'b O5'b -53.9(17) . . . . ?
C19'b O5'b C23'b C22'b 47.9(16) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1438171'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H32 O5'
_chemical_formula_sum            'C26 H32 O5'
_chemical_formula_weight         424.52

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7034(4)
_cell_length_b                   9.1817(4)
_cell_length_c                   16.3996(9)
_cell_angle_alpha                92.963(3)
_cell_angle_beta                 104.082(3)
_cell_angle_gamma                117.611(2)
_cell_volume                     1105.56(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4476
_cell_measurement_theta_min      1.30
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15987
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         26.39
_reflns_number_total             4476
_reflns_number_gt                3959
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0289P)²+2.2889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0095(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4476
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1832
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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
C1 C 0.8909(4) 0.3268(4) 0.23584(18) 0.0323(6) Uani 1 1 d . . .
C14 C 0.4806(4) 0.1683(4) 0.29608(19) 0.0349(7) Uani 1 1 d . . .
H14 H 0.3488 0.0976 0.2707 0.042 Uiso 1 1 calc R . .
C9 C 0.7669(4) 0.1437(4) 0.34080(17) 0.0297(6) Uani 1 1 d . . .
H9 H 0.8155 0.0708 0.3282 0.036 Uiso 1 1 calc R . .
C8 C 0.5732(4) 0.0684(4) 0.27627(18) 0.0318(6) Uani 1 1 d . . .
C19 C 0.9368(4) 0.2051(4) 0.50380(19) 0.0389(7) Uani 1 1 d . . .
H19A H 1.0167 0.1752 0.4841 0.047 Uiso 1 1 calc R . .
H19B H 0.9953 0.3263 0.5173 0.047 Uiso 1 1 calc R . .
C18 C 0.4534(4) -0.1154(4) 0.2820(2) 0.0413(7) Uani 1 1 d . . .
H18A H 0.3401 -0.1637 0.2370 0.062 Uiso 1 1 calc R . .
H18B H 0.4304 -0.1197 0.3365 0.062 Uiso 1 1 calc R . .
H18C H 0.5151 -0.1773 0.2763 0.062 Uiso 1 1 calc R . .
C12 C 0.6436(5) 0.2128(4) 0.4495(2) 0.0397(7) Uani 1 1 d . . .
H12 H 0.6630 0.2544 0.5061 0.048 Uiso 1 1 calc R . .
C15 C 0.4429(6) 0.4015(5) 0.2654(2) 0.0542(9) Uani 1 1 d . . .
H15A H 0.3141 0.3273 0.2374 0.065 Uiso 1 1 calc R . .
H15B H 0.4826 0.4965 0.2368 0.065 Uiso 1 1 calc R . .
C11 C 0.7554(4) 0.1361(4) 0.43283(18) 0.0342(7) Uani 1 1 d . . .
H11 H 0.6857 0.0170 0.4345 0.041 Uiso 1 1 calc R . .
C10 C 0.8925(4) 0.3156(4) 0.32664(19) 0.0338(6) Uani 1 1 d . . .
C7 C 0.5779(4) 0.0748(4) 0.18355(19) 0.0341(6) Uani 1 1 d . . .
C2 C 1.0388(5) 0.4563(4) 0.2190(2) 0.0423(8) Uani 1 1 d . . .
H2 H 1.1349 0.5377 0.2640 0.051 Uiso 1 1 calc R . .
C25 C 1.3429(6) 0.2293(6) 0.9748(2) 0.0618(11) Uani 1 1 d . . .
H25A H 1.4285 0.2991 1.0294 0.074 Uiso 1 1 calc R . .
H25B H 1.3264 0.1173 0.9744 0.074 Uiso 1 1 calc R . .
C24 C 1.1636(7) 0.2242(7) 0.9641(3) 0.0717(13) Uani 1 1 d . . .
H24A H 1.1826 0.3374 0.9726 0.086 Uiso 1 1 calc R . .
H24B H 1.1098 0.1684 1.0066 0.086 Uiso 1 1 calc R . .
C16 C 0.4719(6) 0.4624(5) 0.3581(3) 0.0523(9) Uani 1 1 d . . .
H16A H 0.3976 0.5138 0.3614 0.063 Uiso 1 1 calc R . .
H16B H 0.5983 0.5463 0.3848 0.063 Uiso 1 1 calc R . .
C13 C 0.5198(4) 0.2256(4) 0.3897(2) 0.0362(7) Uani 1 1 d . . .
C22 C 1.1277(5) 0.2112(6) 0.8096(2) 0.0528(9) Uani 1 1 d . . .
H22 H 1.1549 0.3281 0.8157 0.063 Uiso 1 1 calc R . .
C6 C 0.7434(4) 0.2067(4) 0.16798(18) 0.0328(6) Uani 1 1 d . . .
C17 C 0.4216(5) 0.3171(5) 0.4058(2) 0.0483(8) Uani 1 1 d . . .
H17A H 0.4564 0.3588 0.4667 0.058 Uiso 1 1 calc R . .
H17B H 0.2912 0.2419 0.3857 0.058 Uiso 1 1 calc R . .
C5 C 0.7495(5) 0.2181(4) 0.0842(2) 0.0409(7) Uani 1 1 d . . .
H5 H 0.6520 0.1402 0.0386 0.049 Uiso 1 1 calc R . .
C3 C 1.0433(5) 0.4642(5) 0.1359(2) 0.0515(9) Uani 1 1 d . . .
H3 H 1.1430 0.5500 0.1248 0.062 Uiso 1 1 calc R . .
C21 C 1.0687(5) 0.2079(5) 0.6610(2) 0.0492(9) Uani 1 1 d . . .
H21A H 1.1639 0.1909 0.6492 0.059 Uiso 1 1 calc R . .
H21B H 1.1150 0.3272 0.6768 0.059 Uiso 1 1 calc R . .
C20 C 0.9050(5) 0.1340(5) 0.5837(2) 0.0512(9) Uani 1 1 d . . .
H20A H 0.8115 0.1508 0.5975 0.061 Uiso 1 1 calc R . .
H20B H 0.8588 0.0142 0.5707 0.061 Uiso 1 1 calc R . .
C23 C 1.0355(6) 0.1302(7) 0.8744(3) 0.0755(15) Uani 1 1 d . . .
H23A H 1.0061 0.0138 0.8678 0.091 Uiso 1 1 calc R . .
H23B H 0.9233 0.1342 0.8656 0.091 Uiso 1 1 calc R . .
C4 C 0.8991(5) 0.3441(5) 0.0689(2) 0.0489(9) Uani 1 1 d . . .
H4 H 0.9035 0.3488 0.0129 0.059 Uiso 1 1 calc R . .
C26 C 1.4172(6) 0.2985(6) 0.9034(3) 0.0633(11) Uani 1 1 d . . .
H26A H 1.4446 0.4142 0.9074 0.076 Uiso 1 1 calc R . .
H26B H 1.5296 0.2961 0.9093 0.076 Uiso 1 1 calc R . .
O3 O 0.5404(3) 0.3144(3) 0.25660(14) 0.0426(6) Uani 1 1 d . . .
O2 O 0.4465(3) -0.0221(3) 0.12407(14) 0.0499(6) Uani 1 1 d . . .
O1 O 0.9962(4) 0.4360(3) 0.38341(14) 0.0532(7) Uani 1 1 d . . .
O5 O 1.2904(3) 0.2041(4) 0.82151(16) 0.0552(7) Uani 1 1 d . . .
O4 O 1.0143(4) 0.1257(4) 0.72896(16) 0.0633(8) 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 C2 1.392(4) . ?
C1 C6 1.403(4) . ?
C1 C10 1.495(4) . ?
C14 O3 1.448(4) . ?
C14 C13 1.499(4) . ?
C14 C8 1.542(4) . ?
C14 H14 0.9800 . ?
C9 C10 1.517(4) . ?
C9 C11 1.540(4) . ?
C9 C8 1.554(4) . ?
C9 H9 0.9800 . ?
C8 C7 1.534(4) . ?
C8 C18 1.542(4) . ?
C19 C20 1.522(4) . ?
C19 C11 1.533(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C12 C13 1.323(5) . ?
C12 C11 1.504(4) . ?
C12 H12 0.9300 . ?
C15 O3 1.434(4) . ?
C15 C16 1.512(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C11 H11 0.9800 . ?
C10 O1 1.210(4) . ?
C7 O2 1.214(4) . ?
C7 C6 1.484(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C25 C26 1.503(6) . ?
C25 C24 1.505(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C24 C23 1.527(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C16 C17 1.521(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C13 C17 1.504(4) . ?
C22 O4 1.371(4) . ?
C22 O5 1.414(4) . ?
C22 C23 1.506(5) . ?
C22 H22 0.9800 . ?
C6 C5 1.395(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C5 C4 1.375(5) . ?
C5 H5 0.9300 . ?
C3 C4 1.385(5) . ?
C3 H3 0.9300 . ?
C21 O4 1.432(4) . ?
C21 C20 1.494(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C4 H4 0.9300 . ?
C26 O5 1.430(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0(3) . . ?
C2 C1 C10 119.4(3) . . ?
C6 C1 C10 120.6(3) . . ?
O3 C14 C13 108.2(2) . . ?
O3 C14 C8 108.8(2) . . ?
C13 C14 C8 114.3(3) . . ?
O3 C14 H14 108.4 . . ?
C13 C14 H14 108.4 . . ?
C8 C14 H14 108.4 . . ?
C10 C9 C11 115.2(2) . . ?
C10 C9 C8 110.9(2) . . ?
C11 C9 C8 110.1(2) . . ?
C10 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C8 C9 H9 106.7 . . ?
C7 C8 C18 108.3(2) . . ?
C7 C8 C14 107.2(2) . . ?
C18 C8 C14 108.1(2) . . ?
C7 C8 C9 112.0(2) . . ?
C18 C8 C9 110.9(2) . . ?
C14 C8 C9 110.2(2) . . ?
C20 C19 C11 110.2(3) . . ?
C20 C19 H19A 109.6 . . ?
C11 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C11 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C12 C11 125.0(3) . . ?
C13 C12 H12 117.5 . . ?
C11 C12 H12 117.5 . . ?
O3 C15 C16 112.1(3) . . ?
O3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
O3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C12 C11 C19 112.5(3) . . ?
C12 C11 C9 109.4(2) . . ?
C19 C11 C9 116.1(2) . . ?
C12 C11 H11 106.0 . . ?
C19 C11 H11 106.0 . . ?
C9 C11 H11 106.0 . . ?
O1 C10 C1 120.3(3) . . ?
O1 C10 C9 124.3(3) . . ?
C1 C10 C9 115.3(2) . . ?
O2 C7 C6 120.7(3) . . ?
O2 C7 C8 120.7(3) . . ?
C6 C7 C8 118.5(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C26 C25 C24 110.0(3) . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25B 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C25 C24 C23 109.7(4) . . ?
C25 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
C25 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
C15 C16 C17 110.4(3) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C12 C13 C14 122.5(3) . . ?
C12 C13 C17 124.8(3) . . ?
C14 C13 C17 112.3(3) . . ?
O4 C22 O5 108.4(3) . . ?
O4 C22 C23 109.0(3) . . ?
O5 C22 C23 110.2(3) . . ?
O4 C22 H22 109.7 . . ?
O5 C22 H22 109.7 . . ?
C23 C22 H22 109.7 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 119.7(3) . . ?
C1 C6 C7 121.2(3) . . ?
C13 C17 C16 108.4(3) . . ?
C13 C17 H17A 110.0 . . ?
C16 C17 H17A 110.0 . . ?
C13 C17 H17B 110.0 . . ?
C16 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O4 C21 C20 107.5(3) . . ?
O4 C21 H21A 110.2 . . ?
C20 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
C20 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C20 C19 115.2(3) . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C22 C23 C24 108.8(4) . . ?
C22 C23 H23A 109.9 . . ?
C24 C23 H23A 109.9 . . ?
C22 C23 H23B 109.9 . . ?
C24 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O5 C26 C25 111.3(3) . . ?
O5 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
O5 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C15 O3 C14 110.8(2) . . ?
C22 O5 C26 110.7(3) . . ?
C22 O4 C21 114.8(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
O3 C14 C8 C7 -38.9(3) . . . . ?
C13 C14 C8 C7 -160.0(2) . . . . ?
O3 C14 C8 C18 -155.5(2) . . . . ?
C13 C14 C8 C18 83.4(3) . . . . ?
O3 C14 C8 C9 83.2(3) . . . . ?
C13 C14 C8 C9 -37.9(3) . . . . ?
C10 C9 C8 C7 50.8(3) . . . . ?
C11 C9 C8 C7 179.5(2) . . . . ?
C10 C9 C8 C18 172.0(2) . . . . ?
C11 C9 C8 C18 -59.4(3) . . . . ?
C10 C9 C8 C14 -68.4(3) . . . . ?
C11 C9 C8 C14 60.3(3) . . . . ?
C13 C12 C11 C19 154.4(3) . . . . ?
C13 C12 C11 C9 23.8(4) . . . . ?
C20 C19 C11 C12 73.8(4) . . . . ?
C20 C19 C11 C9 -159.1(3) . . . . ?
C10 C9 C11 C12 74.5(3) . . . . ?
C8 C9 C11 C12 -51.8(3) . . . . ?
C10 C9 C11 C19 -54.2(4) . . . . ?
C8 C9 C11 C19 179.6(3) . . . . ?
C2 C1 C10 O1 17.8(5) . . . . ?
C6 C1 C10 O1 -163.2(3) . . . . ?
C2 C1 C10 C9 -158.2(3) . . . . ?
C6 C1 C10 C9 20.7(4) . . . . ?
C11 C9 C10 O1 9.6(4) . . . . ?
C8 C9 C10 O1 135.4(3) . . . . ?
C11 C9 C10 C1 -174.6(2) . . . . ?
C8 C9 C10 C1 -48.7(3) . . . . ?
C18 C8 C7 O2 33.4(4) . . . . ?
C14 C8 C7 O2 -83.1(3) . . . . ?
C9 C8 C7 O2 156.0(3) . . . . ?
C18 C8 C7 C6 -149.3(3) . . . . ?
C14 C8 C7 C6 94.3(3) . . . . ?
C9 C8 C7 C6 -26.7(4) . . . . ?
C6 C1 C2 C3 -1.9(5) . . . . ?
C10 C1 C2 C3 177.1(3) . . . . ?
C26 C25 C24 C23 53.2(5) . . . . ?
O3 C15 C16 C17 -55.4(4) . . . . ?
C11 C12 C13 C14 -2.1(5) . . . . ?
C11 C12 C13 C17 -173.7(3) . . . . ?
O3 C14 C13 C12 -112.1(3) . . . . ?
C8 C14 C13 C12 9.4(4) . . . . ?
O3 C14 C13 C17 60.5(3) . . . . ?
C8 C14 C13 C17 -178.0(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C10 C1 C6 C5 -177.9(3) . . . . ?
C2 C1 C6 C7 -175.3(3) . . . . ?
C10 C1 C6 C7 5.7(4) . . . . ?
O2 C7 C6 C5 -1.0(5) . . . . ?
C8 C7 C6 C5 -178.3(3) . . . . ?
O2 C7 C6 C1 175.3(3) . . . . ?
C8 C7 C6 C1 -2.0(4) . . . . ?
C12 C13 C17 C16 116.6(4) . . . . ?
C14 C13 C17 C16 -55.8(4) . . . . ?
C15 C16 C17 C13 51.6(4) . . . . ?
C1 C6 C5 C4 0.8(5) . . . . ?
C7 C6 C5 C4 177.2(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
O4 C21 C20 C19 -179.4(3) . . . . ?
C11 C19 C20 C21 -172.8(3) . . . . ?
O4 C22 C23 C24 179.1(4) . . . . ?
O5 C22 C23 C24 60.2(5) . . . . ?
C25 C24 C23 C22 -55.1(5) . . . . ?
C6 C5 C4 C3 -1.9(5) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C24 C25 C26 O5 -56.2(5) . . . . ?
C16 C15 O3 C14 60.7(4) . . . . ?
C13 C14 O3 C15 -61.6(3) . . . . ?
C8 C14 O3 C15 173.7(3) . . . . ?
O4 C22 O5 C26 177.2(3) . . . . ?
C23 C22 O5 C26 -63.6(5) . . . . ?
C25 C26 O5 C22 61.5(4) . . . . ?
O5 C22 O4 C21 -71.9(4) . . . . ?
C23 C22 O4 C21 168.2(4) . . . . ?
C20 C21 O4 C22 -160.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.056
