# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_5cl
_database_code_depnum_ccdc_archive 'CCDC 1504427'
_audit_update_record             
;
2016-09-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H8 Cl O'
_chemical_formula_weight         185.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   11.1071(6)
_cell_length_b                   8.2385(4)
_cell_length_c                   19.1755(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1754.67(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1150
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      63.68

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    3.416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4374
_exptl_absorpt_correction_T_max  0.5071
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7530
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.61
_diffrn_reflns_theta_max         63.68
_reflns_number_total             1423
_reflns_number_gt                1150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1368P)²+0.1210P] 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       0.0132(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1423
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2022
_refine_ls_wR_factor_gt          0.1888
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.86072(9) -0.28122(13) 0.45452(4) 0.0844(6) Uani 1 1 d . . .
O1 O 1.06996(16) 0.0098(2) 0.70499(8) 0.0522(7) Uani 1 1 d . . .
C1 C 0.9213(3) -0.1939(4) 0.52970(15) 0.0589(9) Uani 1 1 d . . .
C2 C 0.8652(3) -0.0614(4) 0.55845(15) 0.0584(9) Uani 1 1 d . . .
H8 H 0.7960 -0.0194 0.5380 0.070 Uiso 1 1 calc R . .
C3 C 0.9126(2) 0.0100(3) 0.61854(13) 0.0490(7) Uani 1 1 d . . .
C4 C 1.0155(2) -0.0581(3) 0.64760(12) 0.0478(7) Uani 1 1 d . . .
C5 C 1.0000 0.1131(4) 0.7500 0.0470(9) Uani 1 2 d S . .
C6 C 0.8646(2) 0.1547(3) 0.65114(14) 0.0545(8) Uani 1 1 d . . .
H1 H 0.8029 0.2110 0.6290 0.065 Uiso 1 1 calc R . .
C7 C 0.9060(3) 0.2097(3) 0.71163(14) 0.0511(8) Uani 1 1 d . . .
C8 C 1.0713(3) -0.1905(3) 0.61797(15) 0.0574(8) Uani 1 1 d . . .
H2 H 1.1406 -0.2338 0.6379 0.069 Uiso 1 1 calc R . .
C9 C 1.0228(3) -0.2587(4) 0.55805(14) 0.0621(9) Uani 1 1 d . . .
H3 H 1.0594 -0.3481 0.5374 0.075 Uiso 1 1 calc R . .
C10 C 0.8608(3) 0.3619(4) 0.74667(17) 0.0663(9) Uani 1 1 d . . .
H5 H 0.8575 0.3439 0.7966 0.080 Uiso 1 1 calc R . .
H4 H 0.7795 0.3839 0.7307 0.080 Uiso 1 1 calc R . .
C11 C 0.9395(3) 0.5103(4) 0.7320(2) 0.0788(10) Uani 1 1 d . . .
H6 H 0.9526 0.5176 0.6821 0.095 Uiso 1 1 calc R . .
H7 H 0.8958 0.6067 0.7462 0.095 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 1.746(3) . ?
O1 C4 1.374(3) . ?
O1 C5 1.440(3) . ?
C1 C9 1.360(5) . ?
C1 C2 1.372(5) . ?
C2 C3 1.397(4) . ?
C2 H8 0.9300 . ?
C3 C4 1.390(4) . ?
C3 C6 1.448(4) . ?
C4 C8 1.377(4) . ?
C5 O1 1.440(3) 3_756 ?
C5 C7 1.505(3) . ?
C5 C7 1.505(3) 3_756 ?
C6 C7 1.327(4) . ?
C6 H1 0.9300 . ?
C7 C10 1.509(4) . ?
C8 C9 1.388(4) . ?
C8 H2 0.9300 . ?
C9 H3 0.9300 . ?
C10 C11 1.529(5) . ?
C10 H5 0.9700 . ?
C10 H4 0.9700 . ?
C11 C11 1.510(7) 3_756 ?
C11 H6 0.9700 . ?
C11 H7 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
C4 O1 C5 118.88(16) . . ?
C9 C1 C2 121.8(3) . . ?
C9 C1 Cl1 119.2(3) . . ?
C2 C1 Cl1 119.0(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H8 120.1 . . ?
C3 C2 H8 120.1 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 C6 117.5(2) . . ?
C2 C3 C6 124.4(3) . . ?
O1 C4 C8 117.1(2) . . ?
O1 C4 C3 121.2(2) . . ?
C8 C4 C3 121.6(2) . . ?
O1 C5 O1 107.5(3) . 3_756 ?
O1 C5 C7 113.19(13) . . ?
O1 C5 C7 103.38(13) 3_756 . ?
O1 C5 C7 103.38(13) . 3_756 ?
O1 C5 C7 113.19(13) 3_756 3_756 ?
C7 C5 C7 116.2(3) . 3_756 ?
C7 C6 C3 122.0(3) . . ?
C7 C6 H1 119.0 . . ?
C3 C6 H1 119.0 . . ?
C6 C7 C5 119.2(2) . . ?
C6 C7 C10 123.8(3) . . ?
C5 C7 C10 116.9(2) . . ?
C4 C8 C9 119.2(3) . . ?
C4 C8 H2 120.4 . . ?
C9 C8 H2 120.4 . . ?
C1 C9 C8 119.6(3) . . ?
C1 C9 H3 120.2 . . ?
C8 C9 H3 120.2 . . ?
C7 C10 C11 113.1(3) . . ?
C7 C10 H5 109.0 . . ?
C11 C10 H5 109.0 . . ?
C7 C10 H4 109.0 . . ?
C11 C10 H4 109.0 . . ?
H5 C10 H4 107.8 . . ?
C11 C11 C10 115.2(2) 3_756 . ?
C11 C11 H6 108.5 3_756 . ?
C10 C11 H6 108.5 . . ?
C11 C11 H7 108.5 3_756 . ?
C10 C11 H7 108.5 . . ?
H6 C11 H7 107.5 . . ?

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
C9 C1 C2 C3 -0.1(4) . . . . ?
Cl1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C6 176.7(2) . . . . ?
C5 O1 C4 C8 -161.3(2) . . . . ?
C5 O1 C4 C3 22.3(3) . . . . ?
C2 C3 C4 O1 177.3(2) . . . . ?
C6 C3 C4 O1 -0.3(4) . . . . ?
C2 C3 C4 C8 1.1(4) . . . . ?
C6 C3 C4 C8 -176.5(2) . . . . ?
C4 O1 C5 O1 80.11(18) . . . 3_756 ?
C4 O1 C5 C7 -33.4(3) . . . . ?
C4 O1 C5 C7 -159.92(19) . . . 3_756 ?
C4 C3 C6 C7 -8.8(4) . . . . ?
C2 C3 C6 C7 173.8(3) . . . . ?
C3 C6 C7 C5 -4.1(4) . . . . ?
C3 C6 C7 C10 178.5(2) . . . . ?
O1 C5 C7 C6 24.5(3) . . . . ?
O1 C5 C7 C6 -91.5(3) 3_756 . . . ?
C7 C5 C7 C6 143.9(3) 3_756 . . . ?
O1 C5 C7 C10 -158.0(2) . . . . ?
O1 C5 C7 C10 86.0(3) 3_756 . . . ?
C7 C5 C7 C10 -38.57(19) 3_756 . . . ?
O1 C4 C8 C9 -177.1(2) . . . . ?
C3 C4 C8 C9 -0.7(4) . . . . ?
C2 C1 C9 C8 0.4(4) . . . . ?
Cl1 C1 C9 C8 -179.7(2) . . . . ?
C4 C8 C9 C1 -0.1(4) . . . . ?
C6 C7 C10 C11 -96.9(4) . . . . ?
C5 C7 C10 C11 85.7(3) . . . . ?
C7 C10 C11 C11 -71.8(4) . . . 3_756 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        63.68
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.142
####################################################################### 
# 
# 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_salmo
_database_code_depnum_ccdc_archive 'CCDC 1504532'
_audit_update_record             
;
2016-09-15 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 O4'
_chemical_formula_weight         362.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   8.029(2)
_cell_length_b                   21.258(5)
_cell_length_c                   11.349(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.660(19)
_cell_angle_gamma                90.00
_cell_volume                     1897.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1926
_cell_measurement_theta_min      5.76
_cell_measurement_theta_max      64.30

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            White
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8238
_exptl_absorpt_correction_T_max  0.8399
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       '\\\f and \\\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6231
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.76
_diffrn_reflns_theta_max         64.30
_reflns_number_total             2376
_reflns_number_gt                1926
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1102P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     266
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.050
_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
O2 O 0.6161(3) 0.24234(10) 0.5666(2) 0.0669(6) Uani 1 1 d . . .
O1 O 0.5710(3) 0.33112(11) 0.44534(17) 0.0655(6) Uani 1 1 d . . .
O3 O 0.8443(4) 0.54469(13) 0.6847(3) 0.0925(9) Uani 1 1 d . . .
C8 C 0.4744(4) 0.36445(15) 0.6579(3) 0.0608(8) Uani 1 1 d . . .
H8 H 0.4344 0.3785 0.7246 0.073 Uiso 1 1 calc R . .
C7 C 0.6024(4) 0.40120(15) 0.6158(3) 0.0565(7) Uani 1 1 d . . .
C5 C 0.7850(5) 0.49134(17) 0.6223(3) 0.0667(8) Uani 1 1 d . . .
C6 C 0.6736(5) 0.45539(16) 0.6718(3) 0.0659(8) Uani 1 1 d . . .
H6 H 0.6459 0.4678 0.7441 0.079 Uiso 1 1 calc R . .
C2 C 0.6475(4) 0.38211(14) 0.5089(2) 0.0568(8) Uani 1 1 d . . .
C9 C 0.4126(4) 0.31199(15) 0.6052(2) 0.0558(7) Uani 1 1 d . . .
C1 C 0.4885(5) 0.28488(15) 0.5055(3) 0.0580(8) Uani 1 1 d . . .
C21 C 0.6616(6) 0.19049(16) 0.5071(4) 0.0726(10) Uani 1 1 d . . .
C14 C 0.3595(5) 0.25469(17) 0.4051(3) 0.0672(9) Uani 1 1 d . . .
C3 C 0.7585(5) 0.41739(17) 0.4586(3) 0.0644(8) Uani 1 1 d . . .
H3 H 0.7870 0.4048 0.3868 0.077 Uiso 1 1 calc R . .
C4 C 0.8280(5) 0.47199(18) 0.5156(3) 0.0694(9) Uani 1 1 d . . .
H4 H 0.9039 0.4957 0.4820 0.083 Uiso 1 1 calc R . .
C11 C 0.0950(5) 0.2952(2) 0.5667(4) 0.0777(10) Uani 1 1 d . . .
H11A H 0.0071 0.2801 0.6070 0.093 Uiso 1 1 calc R . .
H11B H 0.0883 0.3408 0.5645 0.093 Uiso 1 1 calc R . .
C20 C 0.8068(7) 0.1591(2) 0.5629(5) 0.0953(14) Uani 1 1 d U . .
H20 H 0.8745 0.1740 0.6337 0.114 Uiso 1 1 calc R . .
C10 C 0.2679(5) 0.27611(17) 0.6408(3) 0.0649(8) Uani 1 1 d . . .
H10A H 0.2690 0.2836 0.7253 0.078 Uiso 1 1 calc R . .
H10B H 0.2847 0.2314 0.6304 0.078 Uiso 1 1 calc R . .
C15 C 0.3987(7) 0.20216(19) 0.3550(3) 0.0792(11) Uani 1 1 d U . .
H15 H 0.3235 0.1860 0.2887 0.095 Uiso 1 1 calc R . .
C16 C 0.5550(7) 0.16922(19) 0.4005(4) 0.0858(12) Uani 1 1 d U . .
C12 C 0.0585(6) 0.2706(2) 0.4385(4) 0.0859(11) Uani 1 1 d . . .
H12A H -0.0511 0.2865 0.3974 0.103 Uiso 1 1 calc R . .
H12B H 0.0508 0.2251 0.4406 0.103 Uiso 1 1 calc R . .
C13 C 0.1934(6) 0.2890(2) 0.3656(3) 0.0803(11) Uani 1 1 d . . .
H13A H 0.1492 0.2801 0.2812 0.096 Uiso 1 1 calc R . .
H13B H 0.2140 0.3339 0.3735 0.096 Uiso 1 1 calc R . .
C22 C 0.9372(8) 0.5870(3) 0.6314(6) 0.120(2) Uani 1 1 d . . .
H22A H 1.0335 0.5660 0.6112 0.180 Uiso 1 1 calc R . .
H22B H 0.9757 0.6208 0.6864 0.180 Uiso 1 1 calc R . .
H22C H 0.8667 0.6037 0.5597 0.180 Uiso 1 1 calc R . .
C17 C 0.6028(10) 0.1145(2) 0.3479(6) 0.1143(18) Uani 1 1 d U A .
H17 H 0.5362 0.0998 0.2766 0.137 Uiso 1 1 calc R . .
C18 C 0.7466(12) 0.0825(2) 0.4001(7) 0.132(2) Uani 1 1 d U . .
C19 C 0.8480(10) 0.1033(3) 0.5074(8) 0.125(2) Uani 1 1 d U A .
H19 H 0.9436 0.0803 0.5427 0.150 Uiso 1 1 calc R . .
O4 O 0.7413(15) 0.0281(5) 0.3177(8) 0.088(4) Uani 0.51(3) 1 d P A 1
C23 C 0.850(2) -0.0181(9) 0.3834(17) 0.113(5) Uani 0.51(3) 1 d P A 1
H23A H 0.9575 0.0008 0.4181 0.169 Uiso 0.51(3) 1 calc PR A 1
H23B H 0.8676 -0.0514 0.3302 0.169 Uiso 0.51(3) 1 calc PR A 1
H23C H 0.7987 -0.0347 0.4461 0.169 Uiso 0.51(3) 1 calc PR A 1
O5 O 0.858(2) 0.0313(4) 0.3794(14) 0.115(6) Uani 0.49(3) 1 d P A 2
C24 C 0.773(4) -0.0085(11) 0.305(3) 0.165(10) Uani 0.49(3) 1 d P A 2
H24A H 0.6839 -0.0263 0.3392 0.248 Uiso 0.49(3) 1 calc PR A 2
H24B H 0.8476 -0.0414 0.2890 0.248 Uiso 0.49(3) 1 calc PR A 2
H24C H 0.7248 0.0125 0.2311 0.248 Uiso 0.49(3) 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
O2 C21 1.380(4) . ?
O2 C1 1.436(4) . ?
O1 C2 1.376(4) . ?
O1 C1 1.433(4) . ?
O3 C5 1.371(4) . ?
O3 C22 1.383(5) . ?
C8 C9 1.314(4) . ?
C8 C7 1.446(5) . ?
C8 H8 0.9300 . ?
C7 C6 1.382(5) . ?
C7 C2 1.395(4) . ?
C5 C6 1.380(5) . ?
C5 C4 1.386(5) . ?
C6 H6 0.9300 . ?
C2 C3 1.374(5) . ?
C9 C1 1.504(5) . ?
C9 C10 1.512(5) . ?
C1 C14 1.518(5) . ?
C21 C20 1.381(7) . ?
C21 C16 1.408(7) . ?
C14 C15 1.319(6) . ?
C14 C13 1.507(6) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C11 C12 1.518(6) . ?
C11 C10 1.525(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C20 C19 1.413(8) . ?
C20 H20 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 C16 1.439(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(6) . ?
C12 C13 1.541(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C17 C18 1.368(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(12) . ?
C18 O5 1.459(13) . ?
C18 O4 1.482(12) . ?
C19 H19 0.9300 . ?
O4 C23 1.42(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O5 C24 1.29(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C21 O2 C1 120.0(3) . . ?
C2 O1 C1 119.4(2) . . ?
C5 O3 C22 118.3(3) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 C8 123.6(3) . . ?
C2 C7 C8 117.1(3) . . ?
O3 C5 C6 115.7(3) . . ?
O3 C5 C4 125.1(3) . . ?
C6 C5 C4 119.2(3) . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C3 C2 O1 118.1(2) . . ?
C3 C2 C7 120.4(3) . . ?
O1 C2 C7 121.2(3) . . ?
C8 C9 C1 119.6(3) . . ?
C8 C9 C10 123.1(3) . . ?
C1 C9 C10 117.3(3) . . ?
O1 C1 O2 108.0(3) . . ?
O1 C1 C9 113.1(3) . . ?
O2 C1 C9 103.7(2) . . ?
O1 C1 C14 104.1(2) . . ?
O2 C1 C14 114.1(3) . . ?
C9 C1 C14 114.1(3) . . ?
O2 C21 C20 116.4(4) . . ?
O2 C21 C16 120.1(4) . . ?
C20 C21 C16 123.3(4) . . ?
C15 C14 C13 123.7(4) . . ?
C15 C14 C1 119.7(4) . . ?
C13 C14 C1 116.6(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C12 C11 C10 114.5(3) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C21 C20 C19 116.9(6) . . ?
C21 C20 H20 121.5 . . ?
C19 C20 H20 121.5 . . ?
C9 C10 C11 112.4(3) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C14 C15 C16 121.6(4) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C21 117.6(5) . . ?
C17 C16 C15 123.2(5) . . ?
C21 C16 C15 119.2(3) . . ?
C11 C12 C13 114.1(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 113.2(3) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C17 C16 120.7(7) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.9(5) . . ?
C17 C18 O5 142.5(10) . . ?
C19 C18 O5 96.2(10) . . ?
C17 C18 O4 101.6(8) . . ?
C19 C18 O4 137.5(8) . . ?
O5 C18 O4 42.0(5) . . ?
C18 C19 C20 120.6(7) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C23 O4 C18 105.7(13) . . ?
C24 O5 C18 109(2) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        64.30
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.052
