# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_exp_578
_database_code_depnum_ccdc_archive 'CCDC 1020854'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2015-07-15 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 H20 O3'
_chemical_formula_weight         308.36

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.35270(18)
_cell_length_b                   13.6016(4)
_cell_length_c                   15.7824(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1578.37(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8984
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         75.41
_reflns_number_total             3114
_reflns_number_gt                3040
_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)+(0.1205P)²+0.3605P] 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       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_number_reflns         3114
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1806
_refine_ls_wR_factor_gt          0.1788
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
O18 O 0.8730(3) 0.32576(14) 0.72952(12) 0.0420(5) Uani 1 1 d . . .
O23 O 0.5149(4) 0.62130(15) 0.92544(13) 0.0554(6) Uani 1 1 d . . .
H23 H 0.5169 0.6033 0.9750 0.083 Uiso 1 1 calc R . .
O20 O 0.8840(3) 0.39812(17) 0.60235(13) 0.0567(6) Uani 1 1 d . . .
C9 C 0.3485(3) 0.27585(16) 0.83310(14) 0.0279(5) Uani 1 1 d . . .
C12 C 0.0637(4) 0.2383(2) 0.94403(15) 0.0381(6) Uani 1 1 d . . .
H12 H -0.0329 0.2256 0.9805 0.046 Uiso 1 1 calc R . .
C2 C 0.3270(3) 0.45950(16) 0.74974(14) 0.0277(5) Uani 1 1 d . . .
C14 C 0.2518(3) 0.35370(16) 0.87019(13) 0.0267(5) Uani 1 1 d . . .
C1 C 0.3274(3) 0.45323(16) 0.84563(13) 0.0274(5) Uani 1 1 d . . .
H1 H 0.2585 0.5071 0.8715 0.033 Uiso 1 1 calc R . .
C10 C 0.3042(4) 0.18000(17) 0.85296(15) 0.0332(5) Uani 1 1 d . . .
H10 H 0.3699 0.1283 0.8295 0.040 Uiso 1 1 calc R . .
C13 C 0.1108(3) 0.33462(17) 0.92535(14) 0.0315(5) Uani 1 1 d . . .
H13 H 0.0473 0.3863 0.9500 0.038 Uiso 1 1 calc R . .
C3 C 0.2552(3) 0.53495(19) 0.70103(16) 0.0358(5) Uani 1 1 d . . .
H3 H 0.1989 0.5885 0.7267 0.043 Uiso 1 1 calc R . .
C8 C 0.4960(3) 0.30898(16) 0.77335(13) 0.0272(5) Uani 1 1 d . . .
H8 H 0.5542 0.2533 0.7447 0.033 Uiso 1 1 calc R . .
C7 C 0.4134(3) 0.38029(16) 0.71099(13) 0.0270(5) Uani 1 1 d . . .
C19 C 0.9127(4) 0.3285(2) 0.64732(17) 0.0404(6) Uani 1 1 d . . .
C15 C 0.5300(3) 0.45213(16) 0.87604(13) 0.0279(5) Uani 1 1 d . . .
H15 H 0.5279 0.4310 0.9354 0.033 Uiso 1 1 calc R . .
C22 C 0.6146(4) 0.55433(19) 0.87525(16) 0.0407(6) Uani 1 1 d . . .
H22A H 0.7383 0.5504 0.8964 0.049 Uiso 1 1 calc R . .
H22B H 0.6194 0.5783 0.8174 0.049 Uiso 1 1 calc R . .
C17 C 0.7858(3) 0.40985(19) 0.76814(16) 0.0362(5) Uani 1 1 d . . .
H17A H 0.7343 0.4522 0.7249 0.043 Uiso 1 1 calc R . .
H17B H 0.8733 0.4475 0.8007 0.043 Uiso 1 1 calc R . .
C11 C 0.1602(4) 0.16084(19) 0.90854(16) 0.0400(6) Uani 1 1 d . . .
H11 H 0.1292 0.0963 0.9217 0.048 Uiso 1 1 calc R . .
C16 C 0.6357(3) 0.37054(16) 0.82609(14) 0.0288(5) Uani 1 1 d . . .
H16 H 0.6923 0.3265 0.8676 0.035 Uiso 1 1 calc R . .
C6 C 0.4250(3) 0.3753(2) 0.62336(15) 0.0357(5) Uani 1 1 d . . .
H6 H 0.4812 0.3221 0.5972 0.043 Uiso 1 1 calc R . .
C4 C 0.2687(4) 0.5293(2) 0.61322(18) 0.0460(7) Uani 1 1 d . . .
H4 H 0.2210 0.5795 0.5799 0.055 Uiso 1 1 calc R . .
C5 C 0.3516(4) 0.4507(2) 0.57539(16) 0.0454(7) Uani 1 1 d . . .
H5 H 0.3588 0.4479 0.5166 0.055 Uiso 1 1 calc R . .
C21 C 0.9960(6) 0.2335(3) 0.6195(3) 0.0686(10) Uani 1 1 d . . .
H21A H 1.0599 0.2043 0.6661 0.103 Uiso 1 1 calc R . .
H21B H 1.0795 0.2457 0.5739 0.103 Uiso 1 1 calc R . .
H21C H 0.9021 0.1897 0.6005 0.103 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
O18 C19 1.330(3) . ?
O18 C17 1.446(3) . ?
O23 C22 1.412(4) . ?
O20 C19 1.202(4) . ?
C9 C10 1.380(3) . ?
C9 C14 1.403(3) . ?
C9 C8 1.506(3) . ?
C12 C13 1.387(4) . ?
C12 C11 1.389(4) . ?
C2 C3 1.387(3) . ?
C2 C7 1.392(3) . ?
C2 C1 1.516(3) . ?
C14 C13 1.378(3) . ?
C14 C1 1.514(3) . ?
C1 C15 1.565(3) . ?
C10 C11 1.399(4) . ?
C3 C4 1.392(4) . ?
C8 C7 1.509(3) . ?
C8 C16 1.565(3) . ?
C7 C6 1.387(3) . ?
C19 C21 1.495(4) . ?
C15 C22 1.523(3) . ?
C15 C16 1.568(3) . ?
C17 C16 1.529(3) . ?
C6 C5 1.384(4) . ?
C4 C5 1.368(4) . ?

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
C19 O18 C17 119.1(2) . . ?
C10 C9 C14 119.9(2) . . ?
C10 C9 C8 126.5(2) . . ?
C14 C9 C8 113.60(19) . . ?
C13 C12 C11 120.2(2) . . ?
C3 C2 C7 120.2(2) . . ?
C3 C2 C1 126.6(2) . . ?
C7 C2 C1 113.21(19) . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 C1 127.3(2) . . ?
C9 C14 C1 112.43(19) . . ?
C14 C1 C2 107.76(18) . . ?
C14 C1 C15 105.23(17) . . ?
C2 C1 C15 107.97(17) . . ?
C9 C10 C11 119.8(2) . . ?
C14 C13 C12 120.0(2) . . ?
C2 C3 C4 118.9(3) . . ?
C9 C8 C7 108.10(19) . . ?
C9 C8 C16 107.45(17) . . ?
C7 C8 C16 105.50(17) . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 C8 126.4(2) . . ?
C2 C7 C8 113.23(18) . . ?
O20 C19 O18 124.0(3) . . ?
O20 C19 C21 125.4(3) . . ?
O18 C19 C21 110.6(3) . . ?
C22 C15 C1 112.18(19) . . ?
C22 C15 C16 116.07(19) . . ?
C1 C15 C16 108.95(17) . . ?
O23 C22 C15 111.9(2) . . ?
O18 C17 C16 107.2(2) . . ?
C12 C11 C10 119.9(2) . . ?
C17 C16 C8 110.03(18) . . ?
C17 C16 C15 114.27(19) . . ?
C8 C16 C15 108.69(18) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C4 C3 120.6(2) . . ?
C4 C5 C6 120.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        75.41
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.061
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate- Hexane'
####################################################################### 
# 
# 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_exp_579
_database_code_depnum_ccdc_archive 'CCDC 1020855'
_audit_update_record             
;
2014-08-25 deposited with the CCDC.
2015-07-15 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 H20 O3'
_chemical_formula_weight         308.36

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.2328(5)
_cell_length_b                   8.8177(4)
_cell_length_c                   11.1343(7)
_cell_angle_alpha                95.635(4)
_cell_angle_beta                 97.037(5)
_cell_angle_gamma                95.431(4)
_cell_volume                     793.65(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3230
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.07
_diffrn_reflns_theta_max         75.36
_reflns_number_total             3230
_reflns_number_gt                2888
_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)+(0.0890P)²+0.1691P] 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       0.008(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3230
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1624
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
O18 O 0.40592(16) 0.62422(13) 0.85249(12) 0.0514(4) Uani 1 1 d . . .
C7 C 0.12477(19) 0.08998(17) 0.69868(14) 0.0382(4) Uani 1 1 d . . .
C2 C 0.22511(19) 0.19788(17) 0.64904(14) 0.0381(4) Uani 1 1 d . . .
O23 O 0.0502(2) 0.16997(17) 1.07469(13) 0.0652(4) Uani 1 1 d . . .
H23 H -0.0472 0.1488 1.0471 0.098 Uiso 1 1 calc R . .
C9 C -0.05079(19) 0.28539(17) 0.75478(13) 0.0374(4) Uani 1 1 d . . .
C3 C 0.3090(2) 0.1518(2) 0.55387(15) 0.0440(4) Uani 1 1 d . . .
H3 H 0.3781 0.2227 0.5221 0.053 Uiso 1 1 calc R . .
C8 C 0.04295(19) 0.15962(16) 0.80225(14) 0.0380(4) Uani 1 1 d . . .
H8 H -0.0290 0.0826 0.8341 0.046 Uiso 1 1 calc R . .
C16 C 0.18506(19) 0.23729(17) 0.90215(14) 0.0389(4) Uani 1 1 d . . .
H16 H 0.2564 0.1581 0.9227 0.047 Uiso 1 1 calc R . .
C15 C 0.29164(19) 0.36294(17) 0.84621(14) 0.0396(4) Uani 1 1 d . . .
H15 H 0.4047 0.3355 0.8519 0.048 Uiso 1 1 calc R . .
C1 C 0.22440(19) 0.35967(17) 0.70820(13) 0.0379(4) Uani 1 1 d . . .
H1 H 0.2895 0.4341 0.6686 0.046 Uiso 1 1 calc R . .
C14 C 0.04708(19) 0.39265(16) 0.70263(13) 0.0373(4) Uani 1 1 d . . .
C6 C 0.1067(2) -0.06272(18) 0.65185(15) 0.0445(4) Uani 1 1 d . . .
H6 H 0.0405 -0.1345 0.6852 0.053 Uiso 1 1 calc R . .
O20 O 0.3243(2) 0.82632(17) 0.95640(17) 0.0841(6) Uani 1 1 d . . .
C10 C -0.2160(2) 0.3010(2) 0.75817(15) 0.0458(4) Uani 1 1 d . . .
H10 H -0.2812 0.2304 0.7934 0.055 Uiso 1 1 calc R . .
C13 C -0.0205(2) 0.51509(19) 0.65516(15) 0.0472(4) Uani 1 1 d . . .
H13 H 0.0448 0.5876 0.6219 0.057 Uiso 1 1 calc R . .
C11 C -0.2832(2) 0.4228(2) 0.70863(17) 0.0556(5) Uani 1 1 d . . .
H11 H -0.3944 0.4333 0.7097 0.067 Uiso 1 1 calc R . .
C4 C 0.2890(2) -0.0017(2) 0.50613(16) 0.0490(4) Uani 1 1 d . . .
H4 H 0.3437 -0.0330 0.4412 0.059 Uiso 1 1 calc R . .
C5 C 0.1887(2) -0.10802(19) 0.55426(16) 0.0493(4) Uani 1 1 d . . .
H5 H 0.1759 -0.2102 0.5214 0.059 Uiso 1 1 calc R . .
C17 C 0.2965(2) 0.52416(19) 0.91090(16) 0.0464(4) Uani 1 1 d . . .
H17A H 0.1871 0.5573 0.9039 0.056 Uiso 1 1 calc R . .
H17B H 0.3375 0.5263 0.9966 0.056 Uiso 1 1 calc R . .
C22 C 0.1184(2) 0.29377(19) 1.01813(15) 0.0486(4) Uani 1 1 d . . .
H22A H 0.2067 0.3525 1.0742 0.058 Uiso 1 1 calc R . .
H22B H 0.0345 0.3610 0.9988 0.058 Uiso 1 1 calc R . .
C12 C -0.1862(3) 0.5289(2) 0.65746(18) 0.0571(5) Uani 1 1 d . . .
H12 H -0.2326 0.6102 0.6244 0.069 Uiso 1 1 calc R . .
C19 C 0.4059(2) 0.7747(2) 0.88244(17) 0.0512(4) Uani 1 1 d . . .
C21 C 0.5176(3) 0.8680(2) 0.8155(2) 0.0616(5) Uani 1 1 d . . .
H21A H 0.5965 0.8057 0.7853 0.092 Uiso 1 1 calc R . .
H21B H 0.5740 0.9534 0.8695 0.092 Uiso 1 1 calc R . .
H21C H 0.4540 0.9050 0.7484 0.092 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
O18 C19 1.336(2) . ?
O18 C17 1.4555(19) . ?
C7 C6 1.383(2) . ?
C7 C2 1.400(2) . ?
C7 C8 1.513(2) . ?
C2 C3 1.383(2) . ?
C2 C1 1.512(2) . ?
O23 C22 1.418(2) . ?
C9 C10 1.385(2) . ?
C9 C14 1.400(2) . ?
C9 C8 1.511(2) . ?
C3 C4 1.392(2) . ?
C8 C16 1.567(2) . ?
C16 C22 1.522(2) . ?
C16 C15 1.572(2) . ?
C15 C17 1.524(2) . ?
C15 C1 1.565(2) . ?
C1 C14 1.510(2) . ?
C14 C13 1.381(2) . ?
C6 C5 1.394(3) . ?
O20 C19 1.207(2) . ?
C10 C11 1.385(3) . ?
C13 C12 1.384(3) . ?
C11 C12 1.383(3) . ?
C4 C5 1.382(3) . ?
C19 C21 1.491(3) . ?

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
C19 O18 C17 116.24(14) . . ?
C6 C7 C2 120.37(15) . . ?
C6 C7 C8 126.45(14) . . ?
C2 C7 C8 113.17(13) . . ?
C3 C2 C7 120.08(14) . . ?
C3 C2 C1 126.92(14) . . ?
C7 C2 C1 112.98(13) . . ?
C10 C9 C14 120.11(15) . . ?
C10 C9 C8 126.83(14) . . ?
C14 C9 C8 113.06(13) . . ?
C2 C3 C4 119.34(16) . . ?
C9 C8 C7 107.27(12) . . ?
C9 C8 C16 107.42(12) . . ?
C7 C8 C16 106.48(12) . . ?
C22 C16 C8 111.25(13) . . ?
C22 C16 C15 114.94(12) . . ?
C8 C16 C15 109.05(12) . . ?
C17 C15 C1 110.18(13) . . ?
C17 C15 C16 113.98(12) . . ?
C1 C15 C16 108.69(11) . . ?
C14 C1 C2 107.52(12) . . ?
C14 C1 C15 106.49(12) . . ?
C2 C1 C15 107.58(12) . . ?
C13 C14 C9 120.13(15) . . ?
C13 C14 C1 126.68(14) . . ?
C9 C14 C1 113.18(13) . . ?
C7 C6 C5 119.32(15) . . ?
C11 C10 C9 119.33(16) . . ?
C14 C13 C12 119.44(16) . . ?
C12 C11 C10 120.48(17) . . ?
C5 C4 C3 120.61(16) . . ?
C4 C5 C6 120.25(15) . . ?
O18 C17 C15 107.03(13) . . ?
O23 C22 C16 111.38(14) . . ?
C11 C12 C13 120.49(16) . . ?
O20 C19 O18 122.56(17) . . ?
O20 C19 C21 125.01(18) . . ?
O18 C19 C21 112.43(16) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        75.36
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane - hexane'
####################################################################### 
# 
# 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_exp_826
_database_code_depnum_ccdc_archive 'CCDC 1054141'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Cl O4'
_chemical_formula_sum            'C23 H23 Cl O4'
_chemical_formula_weight         398.86
_chemical_absolute_configuration syn

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'
Cl Cl 0.3639 0.7018 '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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   10.5625(3)
_cell_length_b                   12.0642(4)
_cell_length_c                   15.9997(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2038.82(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.871
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4965
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.59
_diffrn_reflns_theta_max         71.67
_reflns_number_total             3323
_reflns_number_gt                3110
_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)+(0.0795P)²+0.3343P] 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   -0.01(2)
_refine_ls_number_reflns         3323
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cl21 Cl 0.33784(11) 0.80661(9) 0.96487(5) 0.0834(3) Uani 1 1 d . . .
O25 O 0.46395(18) 0.57649(18) 0.46488(12) 0.0528(5) Uani 1 1 d . . .
O18 O 0.2911(2) 0.73975(16) 0.77712(13) 0.0632(6) Uani 1 1 d . . .
O23 O 0.3586(2) 0.91377(16) 0.76440(13) 0.0637(6) Uani 1 1 d . . .
O27 O 0.6639(2) 0.6217(3) 0.4889(2) 0.1046(11) Uani 1 1 d . . .
C19 C 0.3034(3) 0.8446(2) 0.80153(18) 0.0487(6) Uani 1 1 d . . .
C2 C 0.2544(2) 0.4074(2) 0.72220(16) 0.0429(6) Uani 1 1 d . . .
C7 C 0.3100(2) 0.3612(2) 0.65110(15) 0.0405(5) Uani 1 1 d . . .
C9 C 0.4085(2) 0.53995(19) 0.60996(15) 0.0380(5) Uani 1 1 d . . .
H9 H 0.4925 0.5093 0.6220 0.046 Uiso 1 1 calc R . .
C16 C 0.1411(2) 0.5419(2) 0.63464(18) 0.0456(6) Uani 1 1 d . . .
C26 C 0.5864(3) 0.5796(3) 0.4467(2) 0.0609(8) Uani 1 1 d . . .
C24 C 0.4232(3) 0.6278(2) 0.54200(17) 0.0469(6) Uani 1 1 d . . .
H24A H 0.3430 0.6652 0.5333 0.056 Uiso 1 1 calc R . .
H24B H 0.4851 0.6825 0.5594 0.056 Uiso 1 1 calc R . .
C11 C 0.1927(3) 0.4933(2) 0.56346(16) 0.0446(6) Uani 1 1 d . . .
C8 C 0.3214(2) 0.44251(19) 0.57901(14) 0.0391(5) Uani 1 1 d . . .
H8 H 0.3553 0.4070 0.5287 0.047 Uiso 1 1 calc R . .
C6 C 0.3515(3) 0.2523(2) 0.65180(18) 0.0496(6) Uani 1 1 d . . .
H6 H 0.3891 0.2216 0.6046 0.059 Uiso 1 1 calc R . .
C1 C 0.2222(2) 0.5285(2) 0.71147(16) 0.0437(6) Uani 1 1 d . . .
H1 H 0.1809 0.5590 0.7613 0.052 Uiso 1 1 calc R . .
C10 C 0.3525(2) 0.58660(19) 0.69366(15) 0.0393(5) Uani 1 1 d . . .
H10 H 0.4104 0.5649 0.7386 0.047 Uiso 1 1 calc R . .
C15 C 0.0269(3) 0.5984(3) 0.6297(2) 0.0606(8) Uani 1 1 d . . .
H15 H -0.0078 0.6316 0.6769 0.073 Uiso 1 1 calc R . .
C5 C 0.3363(3) 0.1899(2) 0.7236(2) 0.0597(8) Uani 1 1 d . . .
H5 H 0.3626 0.1164 0.7245 0.072 Uiso 1 1 calc R . .
C3 C 0.2411(3) 0.3451(3) 0.79383(18) 0.0536(7) Uani 1 1 d . . .
H3 H 0.2049 0.3759 0.8415 0.064 Uiso 1 1 calc R . .
C12 C 0.1307(3) 0.4998(3) 0.48784(19) 0.0580(7) Uani 1 1 d . . .
H12 H 0.1651 0.4673 0.4403 0.070 Uiso 1 1 calc R . .
C17 C 0.3427(3) 0.7118(2) 0.69556(18) 0.0506(6) Uani 1 1 d . . .
H17A H 0.4254 0.7453 0.6881 0.061 Uiso 1 1 calc R . .
H17B H 0.2872 0.7379 0.6515 0.061 Uiso 1 1 calc R . .
C4 C 0.2822(3) 0.2360(3) 0.7941(2) 0.0619(8) Uani 1 1 d . . .
H4 H 0.2732 0.1935 0.8422 0.074 Uiso 1 1 calc R . .
C20 C 0.2379(3) 0.8633(2) 0.8845(2) 0.0621(8) Uani 1 1 d . . .
H20 H 0.2305 0.9434 0.8937 0.074 Uiso 1 1 calc R . .
C13 C 0.0147(4) 0.5562(3) 0.4838(3) 0.0757(11) Uani 1 1 d . . .
H13 H -0.0284 0.5605 0.4333 0.091 Uiso 1 1 calc R . .
C14 C -0.0351(3) 0.6044(3) 0.5531(3) 0.0733(10) Uani 1 1 d . . .
H14 H -0.1117 0.6421 0.5493 0.088 Uiso 1 1 calc R . .
C22 C 0.1062(4) 0.8127(3) 0.8903(3) 0.0768(10) Uani 1 1 d . . .
H22A H 0.1126 0.7334 0.8883 0.115 Uiso 1 1 calc R . .
H22B H 0.0557 0.8382 0.8443 0.115 Uiso 1 1 calc R . .
H22C H 0.0673 0.8347 0.9419 0.115 Uiso 1 1 calc R . .
C28 C 0.6116(4) 0.5215(4) 0.3655(2) 0.0896(13) Uani 1 1 d . . .
H28A H 0.5775 0.4478 0.3677 0.134 Uiso 1 1 calc R . .
H28B H 0.7013 0.5178 0.3560 0.134 Uiso 1 1 calc R . .
H28C H 0.5722 0.5618 0.3207 0.134 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
Cl21 C20 1.799(4) . ?
O25 C26 1.326(4) . ?
O25 C24 1.446(3) . ?
O18 C19 1.330(3) . ?
O18 C17 1.454(3) . ?
O23 C19 1.179(3) . ?
O27 C26 1.177(4) . ?
C19 C20 1.515(4) . ?
C2 C3 1.378(4) . ?
C2 C7 1.396(4) . ?
C2 C1 1.510(3) . ?
C7 C6 1.385(4) . ?
C7 C8 1.519(3) . ?
C9 C24 1.526(3) . ?
C9 C10 1.569(3) . ?
C9 C8 1.573(3) . ?
C16 C15 1.388(4) . ?
C16 C11 1.392(4) . ?
C16 C1 1.506(4) . ?
C26 C28 1.501(5) . ?
C11 C12 1.378(4) . ?
C11 C8 1.511(4) . ?
C6 C5 1.383(4) . ?
C1 C10 1.571(3) . ?
C10 C17 1.514(3) . ?
C15 C14 1.392(5) . ?
C5 C4 1.381(5) . ?
C3 C4 1.385(4) . ?
C12 C13 1.403(5) . ?
C20 C22 1.521(5) . ?
C13 C14 1.358(6) . ?

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
C26 O25 C24 117.7(2) . . ?
C19 O18 C17 116.6(2) . . ?
O23 C19 O18 125.0(3) . . ?
O23 C19 C20 124.2(2) . . ?
O18 C19 C20 110.8(2) . . ?
C3 C2 C7 120.2(3) . . ?
C3 C2 C1 126.8(3) . . ?
C7 C2 C1 112.9(2) . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 C8 126.4(2) . . ?
C2 C7 C8 113.2(2) . . ?
C24 C9 C10 113.4(2) . . ?
C24 C9 C8 110.7(2) . . ?
C10 C9 C8 108.43(19) . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 C1 126.4(3) . . ?
C11 C16 C1 113.6(2) . . ?
O27 C26 O25 124.4(3) . . ?
O27 C26 C28 125.1(3) . . ?
O25 C26 C28 110.5(3) . . ?
O25 C24 C9 110.0(2) . . ?
C12 C11 C16 120.6(3) . . ?
C12 C11 C8 126.5(3) . . ?
C16 C11 C8 112.8(2) . . ?
C11 C8 C7 108.4(2) . . ?
C11 C8 C9 105.95(19) . . ?
C7 C8 C9 106.84(19) . . ?
C5 C6 C7 119.1(3) . . ?
C16 C1 C2 108.9(2) . . ?
C16 C1 C10 107.6(2) . . ?
C2 C1 C10 104.8(2) . . ?
C17 C10 C9 113.6(2) . . ?
C17 C10 C1 112.4(2) . . ?
C9 C10 C1 109.00(19) . . ?
C16 C15 C14 119.0(3) . . ?
C4 C5 C6 120.5(3) . . ?
C2 C3 C4 119.3(3) . . ?
C11 C12 C13 118.9(3) . . ?
O18 C17 C10 106.0(2) . . ?
C5 C4 C3 120.6(3) . . ?
C19 C20 C22 114.3(3) . . ?
C19 C20 Cl21 107.6(2) . . ?
C22 C20 Cl21 109.9(2) . . ?
C14 C13 C12 120.6(3) . . ?
C13 C14 C15 120.9(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        71.67
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.047
