# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

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

data_150605
_database_code_depnum_ccdc_archive 'CCDC 1439849'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl O5'
_chemical_formula_weight         362.79

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9475(16)
_cell_length_b                   10.528(2)
_cell_length_c                   11.586(3)
_cell_angle_alpha                93.439(11)
_cell_angle_beta                 108.109(10)
_cell_angle_gamma                96.394(11)
_cell_volume                     911.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    11156
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.90

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   none
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30570
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4195
_reflns_number_gt                3197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0863P)²+0.5808P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1874
_refine_ls_wR_factor_gt          0.1631
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_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
Cl1 Cl 0.23720(11) 0.09905(8) 0.46914(6) 0.0749(3) Uani 1 1 d . . .
O1 O -0.2992(2) -0.1519(2) 0.1060(2) 0.0696(6) Uani 1 1 d . . .
O2 O 0.1467(3) -0.5396(2) -0.1496(2) 0.0810(7) Uani 1 1 d . . .
O3 O 0.3919(3) -0.43603(18) -0.1733(2) 0.0670(5) Uani 1 1 d . . .
O4 O 0.2704(4) -0.1566(2) -0.2922(2) 0.0871(7) Uani 1 1 d . . .
O5 O 0.1100(4) -0.3397(2) -0.3928(2) 0.0853(7) Uani 1 1 d . . .
C1 C 0.20795(18) 0.00801(14) 0.33381(10) 0.0476(5) Uani 1 1 d G . .
C2 C 0.03724(15) -0.04413(14) 0.25977(12) 0.0452(5) Uani 1 1 d G . .
H2A H -0.0614 -0.0309 0.2837 0.054 Uiso 1 1 calc R . .
C3 C 0.01389(12) -0.11598(13) 0.14995(11) 0.0387(4) Uani 1 1 d G . .
C4 C 0.16125(16) -0.13569(12) 0.11417(10) 0.0372(4) Uani 1 1 d G . .
C5 C 0.33196(13) -0.08355(14) 0.18821(13) 0.0456(5) Uani 1 1 d G . .
H5A H 0.4306 -0.0967 0.1643 0.055 Uiso 1 1 calc R . .
C6 C 0.35532(13) -0.01170(14) 0.29804(12) 0.0495(5) Uani 1 1 d G . .
H6A H 0.4695 0.0232 0.3476 0.059 Uiso 1 1 calc R . .
C11 C 0.1570(3) -0.3143(2) -0.1823(2) 0.0460(5) Uani 1 1 d . . .
C12 C 0.2437(3) -0.2260(2) -0.0660(2) 0.0458(5) Uani 1 1 d . . .
H12A H 0.3610 -0.1855 -0.0417 0.055 Uiso 1 1 calc R . .
C13 C 0.1324(3) -0.21328(19) -0.00290(19) 0.0376(4) Uani 1 1 d . . .
C14 C -0.0478(3) -0.2927(2) -0.0654(2) 0.0422(5) Uani 1 1 d . . .
H14A H -0.0544 -0.3717 -0.0254 0.051 Uiso 1 1 calc R . .
C15 C -0.0441(3) -0.3274(2) -0.1945(2) 0.0495(5) Uani 1 1 d . . .
H15A H -0.1043 -0.2691 -0.2500 0.059 Uiso 1 1 calc R . .
H15B H -0.1017 -0.4145 -0.2245 0.059 Uiso 1 1 calc R . .
C16 C -0.1738(3) -0.1635(2) 0.0700(2) 0.0444(5) Uani 1 1 d . . .
C17 C -0.1988(3) -0.2197(2) -0.0570(2) 0.0492(5) Uani 1 1 d . . .
H17A H -0.2075 -0.1511 -0.1099 0.059 Uiso 1 1 calc R . .
H17B H -0.3105 -0.2775 -0.0864 0.059 Uiso 1 1 calc R . .
C21 C 0.4763(5) -0.5533(3) -0.1647(4) 0.0795(9) Uani 1 1 d . . .
H21A H 0.6038 -0.5319 -0.1239 0.095 Uiso 1 1 calc R . .
H21B H 0.4281 -0.6105 -0.1167 0.095 Uiso 1 1 calc R . .
C22 C 0.4452(9) -0.6165(5) -0.2832(5) 0.153(3) Uani 1 1 d . . .
H22A H 0.5018 -0.6929 -0.2760 0.229 Uiso 1 1 calc R . .
H22B H 0.4938 -0.5601 -0.3305 0.229 Uiso 1 1 calc R . .
H22C H 0.3190 -0.6391 -0.3230 0.229 Uiso 1 1 calc R . .
C23 C 0.1182(9) -0.2992(5) -0.5103(4) 0.1261(18) Uani 1 1 d . . .
H23A H 0.0039 -0.3275 -0.5725 0.151 Uiso 1 1 calc R . .
H23B H 0.1390 -0.2061 -0.5042 0.151 Uiso 1 1 calc R . .
C24 C 0.2474(12) -0.3463(6) -0.5447(6) 0.178(3) Uani 1 1 d . . .
H24A H 0.2478 -0.3164 -0.6213 0.267 Uiso 1 1 calc R . .
H24B H 0.2255 -0.4385 -0.5535 0.267 Uiso 1 1 calc R . .
H24C H 0.3611 -0.3178 -0.4840 0.267 Uiso 1 1 calc R . .
C25 C 0.2269(3) -0.4443(2) -0.1671(2) 0.0500(5) Uani 1 1 d . . .
C26 C 0.1905(4) -0.2590(3) -0.2931(3) 0.0585(7) 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
Cl1 C1 1.7246(12) . ?
O1 C16 1.209(3) . ?
O2 C25 1.190(3) . ?
O3 C25 1.329(3) . ?
O3 C21 1.463(3) . ?
O4 C26 1.187(3) . ?
O5 C26 1.330(4) . ?
O5 C23 1.469(4) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C16 1.501(2) . ?
C4 C5 1.3900 . ?
C4 C13 1.480(2) . ?
C5 C6 1.3900 . ?
C11 C12 1.512(3) . ?
C11 C26 1.525(3) . ?
C11 C25 1.533(3) . ?
C11 C15 1.550(3) . ?
C12 C13 1.323(3) . ?
C13 C14 1.514(3) . ?
C14 C17 1.519(3) . ?
C14 C15 1.529(3) . ?
C16 C17 1.498(3) . ?
C21 C22 1.426(6) . ?
C23 C24 1.343(7) . ?

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
C25 O3 C21 117.8(2) . . ?
C26 O5 C23 118.0(3) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 Cl1 120.13(8) . . ?
C6 C1 Cl1 119.86(8) . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 C16 117.84(11) . . ?
C4 C3 C16 122.06(11) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C13 118.81(10) . . ?
C5 C4 C13 121.19(10) . . ?
C4 C5 C6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C12 C11 C26 112.7(2) . . ?
C12 C11 C25 109.5(2) . . ?
C26 C11 C25 109.37(18) . . ?
C12 C11 C15 102.93(17) . . ?
C26 C11 C15 111.0(2) . . ?
C25 C11 C15 111.14(19) . . ?
C13 C12 C11 111.85(19) . . ?
C12 C13 C4 129.62(18) . . ?
C12 C13 C14 111.49(19) . . ?
C4 C13 C14 118.89(15) . . ?
C13 C14 C17 111.11(18) . . ?
C13 C14 C15 103.48(17) . . ?
C17 C14 C15 115.51(19) . . ?
C14 C15 C11 104.86(18) . . ?
O1 C16 C17 121.9(2) . . ?
O1 C16 C3 120.8(2) . . ?
C17 C16 C3 117.27(16) . . ?
C16 C17 C14 113.09(19) . . ?
C22 C21 O3 110.5(3) . . ?
C24 C23 O5 112.8(4) . . ?
O2 C25 O3 124.2(2) . . ?
O2 C25 C11 125.0(2) . . ?
O3 C25 C11 110.81(19) . . ?
O4 C26 O5 124.4(3) . . ?
O4 C26 C11 125.3(3) . . ?
O5 C26 C11 110.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.075

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1439850'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.38

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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1720(19)
_cell_length_b                   9.085(2)
_cell_length_c                   13.302(3)
_cell_angle_alpha                85.887(6)
_cell_angle_beta                 79.292(5)
_cell_angle_gamma                63.379(4)
_cell_volume                     867.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5137
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6560
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2916
_reflns_number_gt                2433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0940P)²+0.5718P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2916
_refine_ls_number_parameters     243
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2574
_refine_ls_wR_factor_gt          0.2480
_refine_ls_goodness_of_fit_ref   1.492
_refine_ls_restrained_S_all      1.501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2912(4) 0.8049(4) 1.1406(3) 0.0659(9) Uani 1 1 d . . .
O2 O 0.7478(5) 0.5658(4) 0.8069(3) 0.0660(10) Uani 1 1 d . . .
O3 O 0.9251(4) 0.5122(4) 0.6517(2) 0.0542(8) Uani 1 1 d . . .
O4 O 1.1277(4) 0.7670(4) 0.6251(2) 0.0619(9) Uani 1 1 d . . .
O5 O 0.8229(4) 0.8842(3) 0.6784(2) 0.0524(8) Uani 1 1 d . A .
C1 C 0.9047(4) 0.8114(4) 1.0433(3) 0.0318(8) Uani 1 1 d . . .
C2 C 0.7136(5) 0.8630(4) 1.0752(3) 0.0370(8) Uani 1 1 d . . .
H2 H 0.6460 0.8441 1.0329 0.044 Uiso 1 1 calc R . .
C3 C 0.6247(6) 0.9411(5) 1.1681(3) 0.0484(10) Uani 1 1 d . . .
H3 H 0.4977 0.9750 1.1877 0.058 Uiso 1 1 calc R . .
C4 C 0.7219(7) 0.9696(5) 1.2325(3) 0.0554(11) Uani 1 1 d . . .
H4 H 0.6606 1.0243 1.2947 0.067 Uiso 1 1 calc R . .
C5 C 0.9097(6) 0.9167(5) 1.2039(3) 0.0501(10) Uani 1 1 d . . .
H5 H 0.9758 0.9345 1.2476 0.060 Uiso 1 1 calc R . .
C6 C 1.0026(5) 0.8371(4) 1.1109(3) 0.0371(8) Uani 1 1 d . . .
C7 C 1.2054(5) 0.7857(4) 1.0815(3) 0.0418(9) Uani 1 1 d . . .
C8 C 1.2949(5) 0.7155(5) 0.9770(3) 0.0424(9) Uani 1 1 d . . .
H8A H 1.4247 0.6418 0.9779 0.051 Uiso 1 1 calc R . .
H8B H 1.2905 0.8046 0.9310 0.051 Uiso 1 1 calc R . .
C9 C 1.2080(4) 0.6215(4) 0.9337(3) 0.0354(8) Uani 1 1 d . . .
H9 H 1.2291 0.5224 0.9745 0.043 Uiso 1 1 calc R . .
C10 C 1.0011(4) 0.7272(4) 0.9439(3) 0.0301(7) Uani 1 1 d . . .
C11 C 0.9094(4) 0.7429(4) 0.8680(3) 0.0326(8) Uani 1 1 d . . .
H11 H 0.7841 0.8171 0.8777 0.039 Uiso 1 1 calc R . .
C12 C 0.9927(4) 0.6501(4) 0.7676(3) 0.0337(8) Uani 1 1 d . . .
C13 C 1.1892(5) 0.5120(4) 0.7697(3) 0.0420(9) Uani 1 1 d . . .
H13A H 1.1808 0.4174 0.8045 0.050 Uiso 1 1 calc R . .
H13B H 1.2535 0.4785 0.7002 0.050 Uiso 1 1 calc R . .
C14 C 1.2989(5) 0.5685(5) 0.8241(3) 0.0444(9) Uani 1 1 d . . .
H14A H 1.4226 0.4794 0.8232 0.053 Uiso 1 1 calc R . .
H14B H 1.3116 0.6600 0.7872 0.053 Uiso 1 1 calc R . .
C15 C 0.8711(5) 0.5733(5) 0.7458(3) 0.0414(9) Uani 1 1 d . . .
C16 C 0.8200(8) 0.4375(7) 0.6186(4) 0.0710(15) Uani 1 1 d . . .
H16A H 0.7718 0.3890 0.6768 0.085 Uiso 1 1 calc R . .
H16B H 0.9009 0.3504 0.5691 0.085 Uiso 1 1 calc R . .
C17 C 0.6654(9) 0.5609(9) 0.5724(5) 0.0932(19) Uani 1 1 d . . .
H17A H 0.5894 0.6501 0.6201 0.112 Uiso 1 1 calc R . .
H17B H 0.5920 0.5113 0.5554 0.112 Uiso 1 1 calc R . .
H17C H 0.7136 0.6020 0.5115 0.112 Uiso 1 1 calc R . .
C18 C 0.9943(5) 0.7708(4) 0.6819(3) 0.0388(9) Uani 1 1 d . . .
C19 C 0.8007(8) 1.0107(7) 0.6023(4) 0.0771(16) Uani 1 1 d DU . .
H19A H 0.833(3) 1.083(3) 0.626(3) 0.093 Uiso 1 1 d D . .
H19B H 0.887(3) 1.004(5) 0.5471(13) 0.093 Uiso 1 1 d D . .
C20 C 0.7039(18) 0.9923(17) 0.5268(8) 0.078(4) Uani 0.462(15) 1 d PDU A 1
H20A H 0.6899 1.0752 0.4757 0.117 Uiso 0.462(15) 1 calc PR A 1
H20B H 0.5835 1.0042 0.5596 0.117 Uiso 0.462(15) 1 calc PR A 1
H20C H 0.7740 0.8852 0.4952 0.117 Uiso 0.462(15) 1 calc PRD A 1
C20A C 0.6348(15) 1.1233(17) 0.5985(11) 0.103(6) Uani 0.538(15) 1 d PD A 2
H20D H 0.6394 1.1994 0.5454 0.155 Uiso 0.538(15) 1 calc PR A 2
H20E H 0.5817 1.1809 0.6631 0.155 Uiso 0.538(15) 1 calc PR A 2
H20F H 0.5598 1.0733 0.5843 0.155 Uiso 0.538(15) 1 calc PR 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
O1 C7 1.215(5) . ?
O2 C15 1.195(5) . ?
O3 C15 1.322(5) . ?
O3 C16 1.448(5) . ?
O4 C18 1.194(4) . ?
O5 C18 1.323(5) . ?
O5 C19 1.447(5) . ?
C1 C2 1.401(5) . ?
C1 C6 1.403(5) . ?
C1 C10 1.474(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(5) . ?
C7 C8 1.485(6) . ?
C8 C9 1.527(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(4) . ?
C9 C14 1.513(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.328(5) . ?
C11 C12 1.506(5) . ?
C11 H11 0.9300 . ?
C12 C15 1.522(5) . ?
C12 C18 1.527(5) . ?
C12 C13 1.536(5) . ?
C13 C14 1.515(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.467(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 C20A 1.289(12) . ?
C19 C20 1.4495(11) . ?
C19 H19A 0.905(10) . ?
C19 H19B 0.901(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 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
C15 O3 C16 117.0(3) . . ?
C18 O5 C19 116.9(3) . . ?
C2 C1 C6 117.7(3) . . ?
C2 C1 C10 121.3(3) . . ?
C6 C1 C10 121.0(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 C7 119.3(3) . . ?
C1 C6 C7 120.4(3) . . ?
O1 C7 C8 122.3(4) . . ?
O1 C7 C6 120.5(4) . . ?
C8 C7 C6 117.2(3) . . ?
C7 C8 C9 115.2(3) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C14 112.1(3) . . ?
C10 C9 C8 109.2(3) . . ?
C14 C9 C8 110.7(3) . . ?
C10 C9 H9 108.2 . . ?
C14 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C11 C10 C1 121.4(3) . . ?
C11 C10 C9 122.2(3) . . ?
C1 C10 C9 116.5(3) . . ?
C10 C11 C12 125.1(3) . . ?
C10 C11 H11 117.5 . . ?
C12 C11 H11 117.5 . . ?
C11 C12 C15 109.3(3) . . ?
C11 C12 C18 109.1(3) . . ?
C15 C12 C18 107.4(3) . . ?
C11 C12 C13 111.5(3) . . ?
C15 C12 C13 108.4(3) . . ?
C18 C12 C13 111.0(3) . . ?
C14 C13 C12 111.1(3) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C9 C14 C13 112.6(3) . . ?
C9 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C9 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O2 C15 O3 125.3(4) . . ?
O2 C15 C12 124.2(4) . . ?
O3 C15 C12 110.4(3) . . ?
O3 C16 C17 110.5(5) . . ?
O3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
O3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 123.5(4) . . ?
O4 C18 C12 126.5(3) . . ?
O5 C18 C12 110.0(3) . . ?
C20A C19 O5 117.7(6) . . ?
C20A C19 C20 61.9(9) . . ?
O5 C19 C20 109.1(6) . . ?
C20A C19 H19A 91.9(12) . . ?
O5 C19 H19A 107(2) . . ?
C20 C19 H19A 142(2) . . ?
C20A C19 H19B 115(2) . . ?
O5 C19 H19B 125(3) . . ?
C20 C19 H19B 83.3(8) . . ?
H19A C19 H19B 84.6(18) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20A H20D 109.5 . . ?
C19 C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19 C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

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
C6 C1 C2 C3 2.2(5) . . . . ?
C10 C1 C2 C3 179.8(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C4 C5 C6 C7 178.3(4) . . . . ?
C2 C1 C6 C5 -2.5(5) . . . . ?
C10 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C10 C1 C6 C7 2.6(5) . . . . ?
C5 C6 C7 O1 4.1(5) . . . . ?
C1 C6 C7 O1 -178.6(3) . . . . ?
C5 C6 C7 C8 -174.2(3) . . . . ?
C1 C6 C7 C8 3.1(5) . . . . ?
O1 C7 C8 C9 150.6(4) . . . . ?
C6 C7 C8 C9 -31.1(5) . . . . ?
C7 C8 C9 C10 51.2(4) . . . . ?
C7 C8 C9 C14 175.1(3) . . . . ?
C2 C1 C10 C11 22.2(5) . . . . ?
C6 C1 C10 C11 -160.3(3) . . . . ?
C2 C1 C10 C9 -157.2(3) . . . . ?
C6 C1 C10 C9 20.3(4) . . . . ?
C14 C9 C10 C11 11.9(5) . . . . ?
C8 C9 C10 C11 135.0(3) . . . . ?
C14 C9 C10 C1 -168.7(3) . . . . ?
C8 C9 C10 C1 -45.6(4) . . . . ?
C1 C10 C11 C12 -174.2(3) . . . . ?
C9 C10 C11 C12 5.2(5) . . . . ?
C10 C11 C12 C15 129.7(3) . . . . ?
C10 C11 C12 C18 -113.1(4) . . . . ?
C10 C11 C12 C13 9.9(5) . . . . ?
C11 C12 C13 C14 -41.0(4) . . . . ?
C15 C12 C13 C14 -161.3(3) . . . . ?
C18 C12 C13 C14 80.9(4) . . . . ?
C10 C9 C14 C13 -43.9(4) . . . . ?
C8 C9 C14 C13 -166.1(3) . . . . ?
C12 C13 C14 C9 59.6(4) . . . . ?
C16 O3 C15 O2 3.2(6) . . . . ?
C16 O3 C15 C12 -178.8(4) . . . . ?
C11 C12 C15 O2 -11.3(5) . . . . ?
C18 C12 C15 O2 -129.6(4) . . . . ?
C13 C12 C15 O2 110.4(4) . . . . ?
C11 C12 C15 O3 170.6(3) . . . . ?
C18 C12 C15 O3 52.4(4) . . . . ?
C13 C12 C15 O3 -67.6(4) . . . . ?
C15 O3 C16 C17 89.5(6) . . . . ?
C19 O5 C18 O4 -1.4(6) . . . . ?
C19 O5 C18 C12 178.7(4) . . . . ?
C11 C12 C18 O4 120.4(4) . . . . ?
C15 C12 C18 O4 -121.2(4) . . . . ?
C13 C12 C18 O4 -2.8(5) . . . . ?
C11 C12 C18 O5 -59.6(4) . . . . ?
C15 C12 C18 O5 58.7(4) . . . . ?
C13 C12 C18 O5 177.1(3) . . . . ?
C18 O5 C19 C20A -179.3(10) . . . . ?
C18 O5 C19 C20 113.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.908
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.075

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1439851'
_audit_update_record             
;
2015-12-01 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl O6'
_chemical_formula_weight         378.79

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9793(12)
_cell_length_b                   11.9540(15)
_cell_length_c                   15.515(2)
_cell_angle_alpha                90.309(7)
_cell_angle_beta                 90.735(7)
_cell_angle_gamma                101.280(7)
_cell_volume                     1814.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6895
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61116
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         27.44
_reflns_number_total             8218
_reflns_number_gt                4660
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0861P)²+1.7887P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8218
_refine_ls_number_parameters     470
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58966(12) 0.29655(10) 0.07394(7) 0.0780(4) Uani 1 1 d . . .
Cl2 Cl 0.19003(13) 0.70383(12) -0.56897(8) 0.0921(4) Uani 1 1 d . . .
O1 O 0.7449(2) 0.58752(19) -0.29487(15) 0.0467(5) Uani 1 1 d . . .
O2 O 0.4003(3) 0.2337(2) -0.2458(2) 0.0848(9) Uani 1 1 d . . .
O3 O 0.4486(4) 0.7818(3) -0.2604(2) 0.0999(12) Uani 1 1 d . . .
O4 O 0.4853(4) 0.8611(3) -0.3867(2) 0.1020(12) Uani 1 1 d . . .
O5 O 0.7394(3) 0.7572(3) -0.48380(19) 0.0750(8) Uani 1 1 d . . .
O6 O 0.7860(3) 0.8736(2) -0.37037(16) 0.0647(7) Uani 1 1 d . . .
O7 O 0.2013(2) 0.40796(19) -0.20075(15) 0.0498(6) Uani 1 1 d . . .
O8 O 0.0290(4) 0.7654(2) -0.2523(2) 0.0926(10) Uani 1 1 d . . .
O9 O -0.1859(3) 0.2150(3) -0.2428(2) 0.0869(10) Uani 1 1 d . . .
O10 O -0.1965(3) 0.1469(3) -0.1102(2) 0.0837(9) Uani 1 1 d . . .
O11 O 0.1162(4) 0.2390(3) -0.0139(2) 0.0900(10) Uani 1 1 d . . .
O12 O 0.0941(4) 0.1184(3) -0.12445(19) 0.0817(9) Uani 1 1 d . . .
C1 C 0.5954(4) 0.3751(3) -0.0207(2) 0.0538(9) Uani 1 1 d . . .
C2 C 0.6640(3) 0.4874(3) -0.0200(2) 0.0508(8) Uani 1 1 d . . .
H2A H 0.7059 0.5205 0.0303 0.061 Uiso 1 1 calc R . .
C3 C 0.6694(3) 0.5498(3) -0.0953(2) 0.0462(8) Uani 1 1 d . . .
H3A H 0.7161 0.6252 -0.0953 0.055 Uiso 1 1 calc R . .
C4 C 0.6061(3) 0.5017(3) -0.1706(2) 0.0413(7) Uani 1 1 d . . .
C5 C 0.6104(3) 0.5631(3) -0.2531(2) 0.0403(7) Uani 1 1 d . . .
C6 C 0.6769(3) 0.6796(3) -0.2731(2) 0.0429(7) Uani 1 1 d . . .
H6A H 0.7128 0.7340 -0.2270 0.051 Uiso 1 1 calc R . .
C7 C 0.6078(3) 0.7180(3) -0.3536(2) 0.0466(8) Uani 1 1 d . . .
C8 C 0.5302(3) 0.6040(3) -0.3936(2) 0.0535(9) Uani 1 1 d . . .
H8A H 0.4476 0.6149 -0.4233 0.064 Uiso 1 1 calc R . .
H8B H 0.5873 0.5738 -0.4343 0.064 Uiso 1 1 calc R . .
C9 C 0.4954(3) 0.5230(3) -0.3169(2) 0.0475(8) Uani 1 1 d . . .
H9A H 0.4102 0.5360 -0.2917 0.057 Uiso 1 1 calc R . .
C10 C 0.4823(4) 0.3954(3) -0.3330(2) 0.0571(9) Uani 1 1 d . . .
H10A H 0.4037 0.3683 -0.3703 0.069 Uiso 1 1 calc R . .
H10B H 0.5630 0.3817 -0.3621 0.069 Uiso 1 1 calc R . .
C11 C 0.4660(4) 0.3307(3) -0.2497(3) 0.0572(9) Uani 1 1 d . . .
C12 C 0.5349(3) 0.3882(3) -0.1698(2) 0.0491(8) Uani 1 1 d . . .
C13 C 0.5302(4) 0.3259(3) -0.0936(3) 0.0561(9) Uani 1 1 d . . .
H13A H 0.4826 0.2508 -0.0923 0.067 Uiso 1 1 calc R . .
C14 C 0.5066(4) 0.7911(3) -0.3266(3) 0.0569(9) Uani 1 1 d . . .
C15 C 0.3911(7) 0.9356(6) -0.3672(5) 0.140(3) Uani 1 1 d DU . .
H15A H 0.3057 0.9091 -0.3982 0.168 Uiso 1 1 calc R . .
H15B H 0.3721 0.9323 -0.3060 0.168 Uiso 1 1 calc R . .
C16 C 0.4406(11) 1.0420(7) -0.3885(6) 0.190(4) Uani 1 1 d DU . .
H16A H 0.3762 1.0889 -0.3739 0.285 Uiso 1 1 calc R . .
H16B H 0.4566 1.0461 -0.4494 0.285 Uiso 1 1 calc R . .
H16C H 0.5250 1.0687 -0.3578 0.285 Uiso 1 1 calc R . .
C17 C 0.7165(4) 0.7834(3) -0.4126(2) 0.0508(8) Uani 1 1 d . . .
C18 C 0.8979(5) 0.9442(4) -0.4157(3) 0.0772(13) Uani 1 1 d . . .
H18A H 0.9532 0.8964 -0.4432 0.093 Uiso 1 1 calc R . .
H18B H 0.8620 0.9877 -0.4600 0.093 Uiso 1 1 calc R . .
C19 C 0.9808(6) 1.0211(4) -0.3545(3) 0.0992(17) Uani 1 1 d . . .
H19A H 1.0555 1.0675 -0.3840 0.149 Uiso 1 1 calc R . .
H19B H 1.0159 0.9775 -0.3109 0.149 Uiso 1 1 calc R . .
H19C H 0.9259 1.0691 -0.3283 0.149 Uiso 1 1 calc R . .
C20 C 0.1561(4) 0.6240(4) -0.4750(3) 0.0624(10) Uani 1 1 d . . .
C21 C 0.1690(3) 0.5112(4) -0.4760(3) 0.0589(10) Uani 1 1 d . . .
H21A H 0.1942 0.4780 -0.5261 0.071 Uiso 1 1 calc R . .
C22 C 0.1439(3) 0.4481(3) -0.4015(2) 0.0500(8) Uani 1 1 d . . .
H22A H 0.1535 0.3723 -0.4016 0.060 Uiso 1 1 calc R . .
C23 C 0.1045(3) 0.4960(3) -0.3264(2) 0.0450(8) Uani 1 1 d . . .
C24 C 0.0788(3) 0.4342(3) -0.2443(2) 0.0430(7) Uani 1 1 d . . .
C25 C 0.0892(3) 0.3175(3) -0.2238(2) 0.0451(8) Uani 1 1 d . . .
H25A H 0.0985 0.2629 -0.2696 0.054 Uiso 1 1 calc R . .
C26 C 0.0011(3) 0.2796(3) -0.1448(2) 0.0476(8) Uani 1 1 d . . .
C27 C -0.0204(4) 0.3940(3) -0.1052(2) 0.0550(9) Uani 1 1 d . . .
H27A H -0.1080 0.3843 -0.0769 0.066 Uiso 1 1 calc R . .
H27B H 0.0514 0.4232 -0.0636 0.066 Uiso 1 1 calc R . .
C28 C -0.0158(3) 0.4750(3) -0.1819(2) 0.0488(8) Uani 1 1 d . . .
H28A H -0.1072 0.4633 -0.2084 0.059 Uiso 1 1 calc R . .
C29 C 0.0332(4) 0.6027(3) -0.1652(3) 0.0601(10) Uani 1 1 d . . .
H29A H -0.0316 0.6305 -0.1287 0.072 Uiso 1 1 calc R . .
H29B H 0.1206 0.6152 -0.1350 0.072 Uiso 1 1 calc R . .
C30 C 0.0477(4) 0.6677(3) -0.2476(3) 0.0626(10) Uani 1 1 d . . .
C31 C 0.0904(3) 0.6106(3) -0.3274(3) 0.0533(9) Uani 1 1 d . . .
C32 C 0.1167(4) 0.6740(3) -0.4025(3) 0.0632(11) Uani 1 1 d . . .
H32A H 0.1075 0.7499 -0.4034 0.076 Uiso 1 1 calc R . .
C33 C -0.1360(4) 0.2099(3) -0.1742(3) 0.0552(9) Uani 1 1 d . . .
C34 C -0.3303(6) 0.0745(5) -0.1270(4) 0.1028(17) Uani 1 1 d DU . .
H34A H -0.3848 0.0673 -0.0752 0.123 Uiso 1 1 calc R . .
H34B H -0.3787 0.1072 -0.1719 0.123 Uiso 1 1 calc R . .
C35 C -0.3074(8) -0.0326(6) -0.1531(5) 0.143(3) Uani 1 1 d DU . .
H35A H -0.3933 -0.0824 -0.1654 0.214 Uiso 1 1 calc R . .
H35B H -0.2606 -0.0645 -0.1077 0.214 Uiso 1 1 calc R . .
H35C H -0.2525 -0.0242 -0.2039 0.214 Uiso 1 1 calc R . .
C36 C 0.0760(4) 0.2118(3) -0.0849(3) 0.0584(9) Uani 1 1 d . . .
C37 C 0.1702(7) 0.0447(6) -0.0767(4) 0.125(2) Uani 1 1 d . . .
H37A H 0.2442 0.0916 -0.0441 0.150 Uiso 1 1 calc R . .
H37B H 0.1100 -0.0012 -0.0362 0.150 Uiso 1 1 calc R . .
C38 C 0.2221(10) -0.0248(6) -0.1311(5) 0.161(4) Uani 1 1 d . . .
H38A H 0.2715 -0.0719 -0.0985 0.242 Uiso 1 1 calc R . .
H38B H 0.2826 0.0205 -0.1707 0.242 Uiso 1 1 calc R . .
H38C H 0.1487 -0.0723 -0.1626 0.242 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.743(4) . ?
Cl2 C20 1.747(4) . ?
O1 C6 1.442(4) . ?
O1 C5 1.476(4) . ?
O2 C11 1.218(4) . ?
O3 C14 1.181(5) . ?
O4 C14 1.300(4) . ?
O4 C15 1.450(6) . ?
O5 C17 1.184(4) . ?
O6 C17 1.327(4) . ?
O6 C18 1.453(4) . ?
O7 C25 1.435(4) . ?
O7 C24 1.477(4) . ?
O8 C30 1.220(4) . ?
O9 C33 1.176(4) . ?
O10 C33 1.328(4) . ?
O10 C34 1.461(6) . ?
O11 C36 1.189(5) . ?
O12 C36 1.316(5) . ?
O12 C37 1.468(5) . ?
C1 C13 1.369(5) . ?
C1 C2 1.381(5) . ?
C2 C3 1.386(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3A 0.9300 . ?
C4 C12 1.403(4) . ?
C4 C5 1.477(4) . ?
C5 C6 1.457(4) . ?
C5 C9 1.509(4) . ?
C6 C7 1.535(4) . ?
C6 H6A 0.9800 . ?
C7 C14 1.520(5) . ?
C7 C17 1.526(5) . ?
C7 C8 1.552(5) . ?
C8 C9 1.538(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.524(5) . ?
C9 H9A 0.9800 . ?
C10 C11 1.505(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.505(5) . ?
C12 C13 1.398(5) . ?
C13 H13A 0.9300 . ?
C15 C16 1.317(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.450(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C32 1.369(6) . ?
C20 C21 1.380(6) . ?
C21 C22 1.382(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.391(5) . ?
C22 H22A 0.9300 . ?
C23 C31 1.405(5) . ?
C23 C24 1.476(5) . ?
C24 C25 1.456(4) . ?
C24 C28 1.505(5) . ?
C25 C26 1.534(5) . ?
C25 H25A 0.9800 . ?
C26 C36 1.519(5) . ?
C26 C33 1.519(5) . ?
C26 C27 1.551(5) . ?
C27 C28 1.532(5) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.528(5) . ?
C28 H28A 0.9800 . ?
C29 C30 1.494(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.516(6) . ?
C31 C32 1.394(5) . ?
C32 H32A 0.9300 . ?
C34 C35 1.402(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 C38 1.358(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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
C6 O1 C5 59.91(19) . . ?
C14 O4 C15 116.7(4) . . ?
C17 O6 C18 116.9(3) . . ?
C25 O7 C24 59.98(19) . . ?
C33 O10 C34 118.3(4) . . ?
C36 O12 C37 116.7(4) . . ?
C13 C1 C2 121.2(3) . . ?
C13 C1 Cl1 119.8(3) . . ?
C2 C1 Cl1 119.0(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C12 119.2(3) . . ?
C3 C4 C5 123.6(3) . . ?
C12 C4 C5 117.3(3) . . ?
C6 C5 O1 58.88(19) . . ?
C6 C5 C4 129.3(3) . . ?
O1 C5 C4 115.3(2) . . ?
C6 C5 C9 109.6(3) . . ?
O1 C5 C9 112.1(3) . . ?
C4 C5 C9 117.2(3) . . ?
O1 C6 C5 61.21(19) . . ?
O1 C6 C7 110.1(3) . . ?
C5 C6 C7 108.6(3) . . ?
O1 C6 H6A 120.8 . . ?
C5 C6 H6A 120.8 . . ?
C7 C6 H6A 120.8 . . ?
C14 C7 C17 111.3(3) . . ?
C14 C7 C6 109.4(3) . . ?
C17 C7 C6 109.4(3) . . ?
C14 C7 C8 109.9(3) . . ?
C17 C7 C8 113.2(3) . . ?
C6 C7 C8 103.2(3) . . ?
C9 C8 C7 105.2(3) . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C5 C9 C10 109.3(3) . . ?
C5 C9 C8 103.9(3) . . ?
C10 C9 C8 118.2(3) . . ?
C5 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C11 C10 C9 111.0(3) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C11 C12 119.9(4) . . ?
O2 C11 C10 121.7(4) . . ?
C12 C11 C10 118.4(3) . . ?
C13 C12 C4 119.4(3) . . ?
C13 C12 C11 119.0(3) . . ?
C4 C12 C11 121.6(3) . . ?
C1 C13 C12 120.1(3) . . ?
C1 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
O3 C14 O4 123.6(4) . . ?
O3 C14 C7 124.1(3) . . ?
O4 C14 C7 112.2(3) . . ?
C16 C15 O4 111.9(6) . . ?
C16 C15 H15A 109.2 . . ?
O4 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
O4 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O6 124.7(3) . . ?
O5 C17 C7 126.2(3) . . ?
O6 C17 C7 109.1(3) . . ?
C19 C18 O6 109.1(4) . . ?
C19 C18 H18A 109.9 . . ?
O6 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
O6 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C32 C20 C21 121.5(4) . . ?
C32 C20 Cl2 119.6(3) . . ?
C21 C20 Cl2 118.9(4) . . ?
C20 C21 C22 119.0(4) . . ?
C20 C21 H21A 120.5 . . ?
C22 C21 H21A 120.5 . . ?
C21 C22 C23 121.2(3) . . ?
C21 C22 H22A 119.4 . . ?
C23 C22 H22A 119.4 . . ?
C22 C23 C31 118.6(3) . . ?
C22 C23 C24 123.9(3) . . ?
C31 C23 C24 117.4(3) . . ?
C25 C24 C23 129.4(3) . . ?
C25 C24 O7 58.60(19) . . ?
C23 C24 O7 115.1(2) . . ?
C25 C24 C28 109.4(3) . . ?
C23 C24 C28 117.4(3) . . ?
O7 C24 C28 112.0(3) . . ?
O7 C25 C24 61.42(19) . . ?
O7 C25 C26 110.5(3) . . ?
C24 C25 C26 108.6(3) . . ?
O7 C25 H25A 120.7 . . ?
C24 C25 H25A 120.7 . . ?
C26 C25 H25A 120.7 . . ?
C36 C26 C33 111.5(3) . . ?
C36 C26 C25 109.6(3) . . ?
C33 C26 C25 109.5(3) . . ?
C36 C26 C27 113.5(3) . . ?
C33 C26 C27 109.2(3) . . ?
C25 C26 C27 103.1(3) . . ?
C28 C27 C26 105.0(3) . . ?
C28 C27 H27A 110.7 . . ?
C26 C27 H27A 110.7 . . ?
C28 C27 H27B 110.7 . . ?
C26 C27 H27B 110.7 . . ?
H27A C27 H27B 108.8 . . ?
C24 C28 C29 109.2(3) . . ?
C24 C28 C27 104.2(3) . . ?
C29 C28 C27 118.0(3) . . ?
C24 C28 H28A 108.3 . . ?
C29 C28 H28A 108.3 . . ?
C27 C28 H28A 108.3 . . ?
C30 C29 C28 111.2(3) . . ?
C30 C29 H29A 109.4 . . ?
C28 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
O8 C30 C29 122.4(4) . . ?
O8 C30 C31 119.2(4) . . ?
C29 C30 C31 118.4(3) . . ?
C32 C31 C23 119.9(4) . . ?
C32 C31 C30 118.9(3) . . ?
C23 C31 C30 121.2(3) . . ?
C20 C32 C31 119.7(4) . . ?
C20 C32 H32A 120.2 . . ?
C31 C32 H32A 120.2 . . ?
O9 C33 O10 124.1(4) . . ?
O9 C33 C26 125.0(3) . . ?
O10 C33 C26 110.9(3) . . ?
C35 C34 O10 107.1(5) . . ?
C35 C34 H34A 110.3 . . ?
O10 C34 H34A 110.3 . . ?
C35 C34 H34B 110.3 . . ?
O10 C34 H34B 110.3 . . ?
H34A C34 H34B 108.6 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O11 C36 O12 124.3(4) . . ?
O11 C36 C26 126.2(4) . . ?
O12 C36 C26 109.5(3) . . ?
C38 C37 O12 111.0(5) . . ?
C38 C37 H37A 109.4 . . ?
O12 C37 H37A 109.4 . . ?
C38 C37 H37B 109.4 . . ?
O12 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.057

