# 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_ay03m
_database_code_depnum_ccdc_archive 'CCDC 1056215'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3,3,9,9-tetramethyl-6-phenyl-3,4,8,9,10,12-hexahydro-1H-6,12-methanodibenzo[d,g][1,3]dioxocine-1,11(2H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 O4'
_chemical_formula_sum            'C25 H28 O4'
_chemical_formula_weight         392.47

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   'P1   '
_symmetry_space_group_name_Hall  'P1   '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.7508(11)
_cell_length_b                   10.2102(19)
_cell_length_c                   10.3282(19)
_cell_angle_alpha                60.929(2)
_cell_angle_beta                 80.487(3)
_cell_angle_gamma                76.750(3)
_cell_volume                     514.89(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             210
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany 
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            4878
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3541
_reflns_number_gt                3384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0639P)²+0.0783P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3541
_refine_ls_number_parameters     266
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6314(4) 0.5299(2) 0.3377(2) 0.0414(5) Uani 1 1 d . . .
C2 C 0.5303(5) 0.4208(2) 0.3139(3) 0.0553(6) Uani 1 1 d . . .
H2A H 0.3935 0.3909 0.3838 0.066 Uiso 1 1 calc R . .
H2B H 0.6500 0.3301 0.3349 0.066 Uiso 1 1 calc R . .
C3 C 0.4521(4) 0.4866(2) 0.1561(3) 0.0511(5) Uani 1 1 d . . .
C4 C 0.2703(4) 0.6324(2) 0.1256(2) 0.0432(5) Uani 1 1 d . . .
H4A H 0.2416 0.6873 0.0207 0.052 Uiso 1 1 calc R . .
H4B H 0.1199 0.6053 0.1805 0.052 Uiso 1 1 calc R . .
C5 C 0.3522(3) 0.7337(2) 0.1680(2) 0.0362(4) Uani 1 1 d . . .
C6 C 0.5126(3) 0.6881(2) 0.2693(2) 0.0360(4) Uani 1 1 d . . .
C7 C 0.6667(6) 0.5228(4) 0.0440(3) 0.0768(8) Uani 1 1 d . . .
H7A H 0.6156 0.5617 -0.0540 0.115 Uiso 1 1 calc R . .
H7B H 0.7834 0.4318 0.0673 0.115 Uiso 1 1 calc R . .
H7C H 0.7362 0.5976 0.0480 0.115 Uiso 1 1 calc R . .
C8 C 0.3324(6) 0.3735(3) 0.1457(4) 0.0845(10) Uani 1 1 d . . .
H8A H 0.2926 0.4126 0.0453 0.127 Uiso 1 1 calc R . .
H8B H 0.1892 0.3585 0.2101 0.127 Uiso 1 1 calc R . .
H8C H 0.4401 0.2782 0.1753 0.127 Uiso 1 1 calc R . .
C9 C 0.5752(3) 0.8047(2) 0.3023(2) 0.0369(4) Uani 1 1 d . . .
H9 H 0.7357 0.7710 0.3395 0.044 Uiso 1 1 calc R . .
C10 C 0.5661(3) 0.9521(2) 0.1574(2) 0.0385(4) Uani 1 1 d . . .
H10A H 0.6077 1.0307 0.1720 0.046 Uiso 1 1 calc R . .
H10B H 0.6789 0.9371 0.0829 0.046 Uiso 1 1 calc R . .
C11 C 0.3134(3) 0.9986(2) 0.1076(2) 0.0367(4) Uani 1 1 d . . .
C12 C 0.2664(4) 1.1417(2) -0.0375(2) 0.0384(4) Uani 1 1 d . . .
C13 C 0.0380(4) 1.2238(3) -0.0685(3) 0.0584(6) Uani 1 1 d . . .
H13 H -0.0880 1.1925 0.0022 0.070 Uiso 1 1 calc R . .
C14 C -0.0055(5) 1.3511(3) -0.2026(3) 0.0647(7) Uani 1 1 d . . .
H14 H -0.1609 1.4045 -0.2216 0.078 Uiso 1 1 calc R . .
C15 C 0.1756(5) 1.4004(3) -0.3081(3) 0.0605(6) Uani 1 1 d . . .
H15 H 0.1446 1.4867 -0.3987 0.073 Uiso 1 1 calc R . .
C16 C 0.4017(5) 1.3217(3) -0.2791(3) 0.0706(7) Uani 1 1 d . . .
H16 H 0.5266 1.3546 -0.3502 0.085 Uiso 1 1 calc R . .
C17 C 0.4483(5) 1.1928(3) -0.1445(3) 0.0589(6) Uani 1 1 d . . .
H17 H 0.6042 1.1403 -0.1262 0.071 Uiso 1 1 calc R . .
C18 C 0.1931(4) 0.9384(2) 0.3630(2) 0.0384(4) Uani 1 1 d . . .
C19 C 0.3935(4) 0.8347(2) 0.4120(2) 0.0384(4) Uani 1 1 d . . .
C20 C 0.4332(4) 0.7581(2) 0.5701(2) 0.0451(5) Uani 1 1 d . . .
C21 C 0.2266(5) 0.7803(3) 0.6715(2) 0.0565(6) Uani 1 1 d . . .
H21A H 0.2881 0.7575 0.7635 0.068 Uiso 1 1 calc R . .
H21B H 0.1231 0.7078 0.6951 0.068 Uiso 1 1 calc R . .
C22 C 0.0771(4) 0.9398(3) 0.6083(2) 0.0476(5) Uani 1 1 d . . .
C23 C -0.0025(4) 0.9780(3) 0.4581(2) 0.0474(5) Uani 1 1 d . . .
H23A H -0.1314 0.9238 0.4744 0.057 Uiso 1 1 calc R . .
H23B H -0.0648 1.0861 0.4060 0.057 Uiso 1 1 calc R . .
C24 C 0.2236(5) 1.0566(3) 0.5893(4) 0.0738(8) Uani 1 1 d . . .
H24A H 0.1259 1.1558 0.5507 0.111 Uiso 1 1 calc R . .
H24B H 0.3599 1.0571 0.5215 0.111 Uiso 1 1 calc R . .
H24C H 0.2768 1.0300 0.6837 0.111 Uiso 1 1 calc R . .
C25 C -0.1433(5) 0.9429(4) 0.7138(3) 0.0727(8) Uani 1 1 d . . .
H25A H -0.0926 0.9159 0.8090 0.109 Uiso 1 1 calc R . .
H25B H -0.2378 0.8715 0.7246 0.109 Uiso 1 1 calc R . .
H25C H -0.2373 1.0433 0.6737 0.109 Uiso 1 1 calc R . .
O1 O 0.8056(3) 0.48704(18) 0.41122(18) 0.0576(4) Uani 1 1 d . . .
O2 O 0.2449(2) 0.88066(14) 0.08990(16) 0.0432(3) Uani 1 1 d . . .
O3 O 0.1460(2) 1.02094(16) 0.21692(15) 0.0435(3) Uani 1 1 d . . .
O4 O 0.6241(3) 0.6796(2) 0.61709(18) 0.0642(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.225(3) . ?
C1 C6 1.456(3) . ?
C1 C2 1.500(3) . ?
C2 C3 1.533(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.523(4) . ?
C3 C8 1.525(3) . ?
C3 C4 1.532(3) . ?
C4 C5 1.489(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.346(3) . ?
C5 O2 1.359(2) . ?
C6 C9 1.515(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C19 1.506(3) . ?
C9 C10 1.519(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.429(2) . ?
C11 O2 1.447(2) . ?
C11 C12 1.509(3) . ?
C12 C17 1.377(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.358(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.348(3) . ?
C18 O3 1.362(2) . ?
C18 C23 1.485(3) . ?
C19 C20 1.460(3) . ?
C20 O4 1.216(3) . ?
C20 C21 1.502(3) . ?
C21 C22 1.526(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.528(3) . ?
C22 C24 1.532(4) . ?
C22 C25 1.534(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O1 C1 C6 122.00(19) . . ?
O1 C1 C2 121.20(18) . . ?
C6 C1 C2 116.80(18) . . ?
C1 C2 C3 113.48(18) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C7 C3 C8 110.1(2) . . ?
C7 C3 C4 110.1(2) . . ?
C8 C3 C4 109.2(2) . . ?
C7 C3 C2 110.4(2) . . ?
C8 C3 C2 109.9(2) . . ?
C4 C3 C2 107.14(18) . . ?
C5 C4 C3 112.71(17) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 O2 123.62(17) . . ?
C6 C5 C4 125.20(17) . . ?
O2 C5 C4 111.17(16) . . ?
C5 C6 C1 119.06(17) . . ?
C5 C6 C9 119.07(17) . . ?
C1 C6 C9 121.77(17) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C19 C9 C6 111.28(16) . . ?
C19 C9 C10 107.55(16) . . ?
C6 C9 C10 106.75(16) . . ?
C19 C9 H9 110.4 . . ?
C6 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
C11 C10 C9 107.61(16) . . ?
C11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 O2 106.36(15) . . ?
O3 C11 C12 106.46(15) . . ?
O2 C11 C12 105.49(15) . . ?
O3 C11 C10 110.53(15) . . ?
O2 C11 C10 111.09(15) . . ?
C12 C11 C10 116.31(17) . . ?
C17 C12 C13 117.8(2) . . ?
C17 C12 C11 121.30(18) . . ?
C13 C12 C11 120.91(19) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.8(2) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 O3 123.22(18) . . ?
C19 C18 C23 125.40(18) . . ?
O3 C18 C23 111.37(16) . . ?
C18 C19 C20 118.97(18) . . ?
C18 C19 C9 119.51(17) . . ?
C20 C19 C9 121.48(17) . . ?
O4 C20 C19 121.4(2) . . ?
O4 C20 C21 121.8(2) . . ?
C19 C20 C21 116.77(18) . . ?
C20 C21 C22 114.63(19) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 107.78(18) . . ?
C21 C22 C24 110.8(2) . . ?
C23 C22 C24 110.0(2) . . ?
C21 C22 C25 109.6(2) . . ?
C23 C22 C25 109.68(19) . . ?
C24 C22 C25 108.9(2) . . ?
C18 C23 C22 113.36(17) . . ?
C18 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C18 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5 O2 C11 119.62(14) . . ?
C18 O3 C11 119.75(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -140.0(2) . . . . ?
C6 C1 C2 C3 40.0(3) . . . . ?
C1 C2 C3 C7 63.3(3) . . . . ?
C1 C2 C3 C8 -175.1(2) . . . . ?
C1 C2 C3 C4 -56.6(3) . . . . ?
C7 C3 C4 C5 -72.7(2) . . . . ?
C8 C3 C4 C5 166.4(2) . . . . ?
C2 C3 C4 C5 47.4(2) . . . . ?
C3 C4 C5 C6 -24.0(3) . . . . ?
C3 C4 C5 O2 155.57(18) . . . . ?
O2 C5 C6 C1 -174.96(17) . . . . ?
C4 C5 C6 C1 4.5(3) . . . . ?
O2 C5 C6 C9 1.4(3) . . . . ?
C4 C5 C6 C9 -179.05(19) . . . . ?
O1 C1 C6 C5 167.68(19) . . . . ?
C2 C1 C6 C5 -12.3(3) . . . . ?
O1 C1 C6 C9 -8.6(3) . . . . ?
C2 C1 C6 C9 171.40(19) . . . . ?
C5 C6 C9 C19 82.6(2) . . . . ?
C1 C6 C9 C19 -101.0(2) . . . . ?
C5 C6 C9 C10 -34.4(2) . . . . ?
C1 C6 C9 C10 141.87(17) . . . . ?
C19 C9 C10 C11 -58.7(2) . . . . ?
C6 C9 C10 C11 60.8(2) . . . . ?
C9 C10 C11 O3 59.86(19) . . . . ?
C9 C10 C11 O2 -58.0(2) . . . . ?
C9 C10 C11 C12 -178.63(16) . . . . ?
O3 C11 C12 C17 148.2(2) . . . . ?
O2 C11 C12 C17 -99.0(2) . . . . ?
C10 C11 C12 C17 24.6(3) . . . . ?
O3 C11 C12 C13 -33.2(3) . . . . ?
O2 C11 C12 C13 79.5(2) . . . . ?
C10 C11 C12 C13 -156.9(2) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
C11 C12 C13 C14 -177.8(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C13 C12 C17 C16 -0.6(4) . . . . ?
C11 C12 C17 C16 178.0(2) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?
O3 C18 C19 C20 176.67(18) . . . . ?
C23 C18 C19 C20 -3.2(3) . . . . ?
O3 C18 C19 C9 -1.0(3) . . . . ?
C23 C18 C19 C9 179.12(19) . . . . ?
C6 C9 C19 C18 -85.4(2) . . . . ?
C10 C9 C19 C18 31.2(2) . . . . ?
C6 C9 C19 C20 96.9(2) . . . . ?
C10 C9 C19 C20 -146.48(18) . . . . ?
C18 C19 C20 O4 -169.9(2) . . . . ?
C9 C19 C20 O4 7.7(3) . . . . ?
C18 C19 C20 C21 10.5(3) . . . . ?
C9 C19 C20 C21 -171.9(2) . . . . ?
O4 C20 C21 C22 142.7(2) . . . . ?
C19 C20 C21 C22 -37.7(3) . . . . ?
C20 C21 C22 C23 54.2(3) . . . . ?
C20 C21 C22 C24 -66.2(3) . . . . ?
C20 C21 C22 C25 173.5(2) . . . . ?
C19 C18 C23 C22 22.4(3) . . . . ?
O3 C18 C23 C22 -157.43(17) . . . . ?
C21 C22 C23 C18 -45.4(3) . . . . ?
C24 C22 C23 C18 75.5(2) . . . . ?
C25 C22 C23 C18 -164.7(2) . . . . ?
C6 C5 O2 C11 3.9(3) . . . . ?
C4 C5 O2 C11 -175.71(16) . . . . ?
O3 C11 O2 C5 -94.92(18) . . . . ?
C12 C11 O2 C5 152.26(17) . . . . ?
C10 C11 O2 C5 25.4(2) . . . . ?
C19 C18 O3 C11 0.3(3) . . . . ?
C23 C18 O3 C11 -179.80(17) . . . . ?
O2 C11 O3 C18 90.16(19) . . . . ?
C12 C11 O3 C18 -157.70(16) . . . . ?
C10 C11 O3 C18 -30.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ay56m
_database_code_depnum_ccdc_archive 'CCDC 1056216'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"'2,2'-(3-(4-chlorophenyl)-3-oxopropane-1, 1-diyl) bis (3-hydroxy-5, 5-dimethylcyclohex-2-enone)'"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H29 Cl O5'
_chemical_formula_sum            'C25 H29 Cl O5'
_chemical_formula_weight         444.93

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           Monoclinic
_symmetry_space_group_name_H-M   'I2/a  '
_symmetry_space_group_name_Hall  '-I 2ya '

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

_cell_length_a                   19.0793(11)
_cell_length_b                   11.3954(7)
_cell_length_c                   22.0551(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.7630(10)
_cell_angle_gamma                90.00
_cell_volume                     4739.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8574
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9266
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            20502
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4183
_reflns_number_gt                3429
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0630P)²+2.1323P] 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         4183
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.03382(4) 1.38202(8) 0.42507(4) 0.1321(3) Uani 1 1 d . . .
O5 O 0.33695(8) 0.80772(13) 0.46913(5) 0.0755(4) Uani 1 1 d . . .
C7 C 0.24763(9) 1.07197(16) 0.33198(7) 0.0596(4) Uani 1 1 d . . .
C9 C 0.33295(9) 0.89766(15) 0.34269(7) 0.0602(4) Uani 1 1 d . . .
H9 H 0.3230 0.8935 0.2978 0.072 Uiso 1 1 calc R . .
O2 O 0.38897(9) 1.01417(13) 0.45761(6) 0.0911(5) Uani 1 1 d . . .
C4 C 0.19339(8) 1.14552(14) 0.35628(7) 0.0563(4) Uani 1 1 d . . .
C10 C 0.40115(9) 0.96764(14) 0.35620(7) 0.0563(4) Uani 1 1 d . . .
C17 C 0.44709(9) 0.97146(16) 0.31344(7) 0.0619(4) Uani 1 1 d . . .
C18 C 0.33882(9) 0.77076(15) 0.36351(7) 0.0598(4) Uani 1 1 d . . .
O1 O 0.27349(8) 1.10412(13) 0.28794(6) 0.0881(4) Uani 1 1 d . . .
O3 O 0.43724(8) 0.90966(14) 0.26292(6) 0.0866(4) Uani 1 1 d D . .
C19 C 0.33614(9) 0.73548(16) 0.42293(8) 0.0620(4) Uani 1 1 d . . .
C16 C 0.51252(9) 1.04440(18) 0.32126(8) 0.0701(5) Uani 1 1 d . . .
H16A H 0.5201 1.0729 0.2813 0.084 Uiso 1 1 calc R . .
H16B H 0.5526 0.9952 0.3371 0.084 Uiso 1 1 calc R . .
C11 C 0.42205(10) 1.02654(15) 0.41213(7) 0.0649(4) Uani 1 1 d . . .
O4 O 0.36345(10) 0.71010(14) 0.26738(6) 0.0983(5) Uani 1 1 d . . .
C3 C 0.17557(10) 1.13148(17) 0.41440(8) 0.0709(5) Uani 1 1 d . . .
H3A H 0.1970 1.0723 0.4397 0.085 Uiso 1 1 calc R . .
C13 C 0.51067(9) 1.14890(17) 0.36394(8) 0.0637(4) Uani 1 1 d . . .
C5 C 0.15963(10) 1.23267(17) 0.31925(8) 0.0711(5) Uani 1 1 d . . .
H5A H 0.1706 1.2432 0.2799 0.085 Uiso 1 1 calc R . .
C8 C 0.26698(10) 0.95628(17) 0.36155(9) 0.0741(5) Uani 1 1 d . . .
H8A H 0.2270 0.9034 0.3517 0.089 Uiso 1 1 calc R . .
H8B H 0.2749 0.9670 0.4057 0.089 Uiso 1 1 calc R . .
C20 C 0.33236(11) 0.60979(17) 0.44033(9) 0.0751(5) Uani 1 1 d . . .
H20A H 0.3023 0.6027 0.4719 0.090 Uiso 1 1 calc R . .
H20B H 0.3795 0.5834 0.4578 0.090 Uiso 1 1 calc R . .
C1 C 0.09443(10) 1.28895(18) 0.39782(10) 0.0790(5) Uani 1 1 d . . .
C25 C 0.34918(10) 0.68351(18) 0.31990(9) 0.0726(5) Uani 1 1 d . . .
C12 C 0.48634(11) 1.10292(18) 0.42188(8) 0.0749(5) Uani 1 1 d . . .
H12A H 0.5250 1.0588 0.4450 0.090 Uiso 1 1 calc R . .
H12B H 0.4768 1.1694 0.4468 0.090 Uiso 1 1 calc R . .
C2 C 0.12665(12) 1.20374(19) 0.43524(10) 0.0837(6) Uani 1 1 d . . .
H2 H 0.1157 1.1944 0.4746 0.100 Uiso 1 1 calc R . .
C21 C 0.30368(11) 0.52941(17) 0.38699(10) 0.0767(5) Uani 1 1 d . . .
C15 C 0.58401(11) 1.2036(2) 0.37938(9) 0.0873(6) Uani 1 1 d . . .
H15A H 0.5813 1.2719 0.4044 0.131 Uiso 1 1 calc R . .
H15B H 0.6009 1.2256 0.3422 0.131 Uiso 1 1 calc R . .
H15C H 0.6160 1.1478 0.4013 0.131 Uiso 1 1 calc R . .
C24 C 0.34600(12) 0.55575(18) 0.33521(10) 0.0808(6) Uani 1 1 d . . .
H24A H 0.3940 0.5267 0.3467 0.097 Uiso 1 1 calc R . .
H24B H 0.3249 0.5135 0.2988 0.097 Uiso 1 1 calc R . .
C6 C 0.10992(11) 1.30428(19) 0.33977(10) 0.0819(6) Uani 1 1 d . . .
H6 H 0.0872 1.3624 0.3144 0.098 Uiso 1 1 calc R . .
C14 C 0.45930(11) 1.24174(19) 0.33338(11) 0.0889(6) Uani 1 1 d . . .
H14A H 0.4126 1.2086 0.3242 0.133 Uiso 1 1 calc R . .
H14B H 0.4746 1.2678 0.2961 0.133 Uiso 1 1 calc R . .
H14C H 0.4584 1.3072 0.3606 0.133 Uiso 1 1 calc R . .
C22 C 0.22475(11) 0.5529(2) 0.36583(13) 0.0993(7) Uani 1 1 d . . .
H22A H 0.2180 0.6342 0.3552 0.149 Uiso 1 1 calc R . .
H22B H 0.1985 0.5340 0.3984 0.149 Uiso 1 1 calc R . .
H22C H 0.2083 0.5052 0.3306 0.149 Uiso 1 1 calc R . .
C23 C 0.31341(14) 0.40121(19) 0.40669(14) 0.1065(8) Uani 1 1 d . . .
H23A H 0.2991 0.3512 0.3720 0.160 Uiso 1 1 calc R . .
H23B H 0.2848 0.3847 0.4379 0.160 Uiso 1 1 calc R . .
H23C H 0.3624 0.3871 0.4226 0.160 Uiso 1 1 calc R . .
H5O H 0.3534(16) 0.888(3) 0.4632(14) 0.150(11) Uiso 1 1 d . . .
H3O H 0.4070(13) 0.8405(16) 0.2642(14) 0.156(12) Uiso 1 1 d 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 1.742(2) . ?
O5 C19 1.308(2) . ?
C7 O1 1.2112(19) . ?
C7 C8 1.492(2) . ?
C7 C4 1.493(2) . ?
C9 C18 1.516(2) . ?
C9 C10 1.516(2) . ?
C9 C8 1.537(2) . ?
O2 C11 1.2718(19) . ?
C4 C5 1.381(2) . ?
C4 C3 1.385(2) . ?
C10 C17 1.383(2) . ?
C10 C11 1.407(2) . ?
C17 O3 1.307(2) . ?
C17 C16 1.488(3) . ?
C18 C19 1.379(2) . ?
C18 C25 1.418(2) . ?
C19 C20 1.487(3) . ?
C16 C13 1.522(3) . ?
C11 C12 1.493(3) . ?
O4 C25 1.266(2) . ?
C3 C2 1.375(3) . ?
C13 C12 1.518(2) . ?
C13 C15 1.522(3) . ?
C13 C14 1.527(3) . ?
C5 C6 1.379(3) . ?
C20 C21 1.525(3) . ?
C1 C2 1.359(3) . ?
C1 C6 1.368(3) . ?
C25 C24 1.498(3) . ?
C21 C24 1.526(3) . ?
C21 C23 1.527(3) . ?
C21 C22 1.531(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
O1 C7 C8 120.91(17) . . ?
O1 C7 C4 120.49(16) . . ?
C8 C7 C4 118.56(14) . . ?
C18 C9 C10 114.87(14) . . ?
C18 C9 C8 110.99(13) . . ?
C10 C9 C8 115.57(15) . . ?
C5 C4 C3 118.19(17) . . ?
C5 C4 C7 118.53(15) . . ?
C3 C4 C7 123.28(15) . . ?
C17 C10 C11 117.28(16) . . ?
C17 C10 C9 119.77(15) . . ?
C11 C10 C9 122.90(14) . . ?
O3 C17 C10 122.73(17) . . ?
O3 C17 C16 114.14(14) . . ?
C10 C17 C16 123.13(15) . . ?
C19 C18 C25 118.00(17) . . ?
C19 C18 C9 123.64(15) . . ?
C25 C18 C9 118.35(14) . . ?
O5 C19 C18 123.99(16) . . ?
O5 C19 C20 113.59(15) . . ?
C18 C19 C20 122.41(16) . . ?
C17 C16 C13 114.26(13) . . ?
O2 C11 C10 122.00(16) . . ?
O2 C11 C12 116.53(15) . . ?
C10 C11 C12 121.42(14) . . ?
C2 C3 C4 121.01(18) . . ?
C12 C13 C16 106.83(15) . . ?
C12 C13 C15 109.98(15) . . ?
C16 C13 C15 110.60(15) . . ?
C12 C13 C14 110.65(16) . . ?
C16 C13 C14 110.05(16) . . ?
C15 C13 C14 108.74(17) . . ?
C6 C5 C4 120.90(17) . . ?
C7 C8 C9 115.09(14) . . ?
C19 C20 C21 113.90(16) . . ?
C2 C1 C6 121.15(19) . . ?
C2 C1 Cl1 119.21(17) . . ?
C6 C1 Cl1 119.63(17) . . ?
O4 C25 C18 121.62(18) . . ?
O4 C25 C24 117.42(17) . . ?
C18 C25 C24 120.93(17) . . ?
C11 C12 C13 115.47(15) . . ?
C1 C2 C3 119.47(19) . . ?
C20 C21 C24 106.90(16) . . ?
C20 C21 C23 109.95(19) . . ?
C24 C21 C23 110.23(18) . . ?
C20 C21 C22 110.54(18) . . ?
C24 C21 C22 110.22(19) . . ?
C23 C21 C22 108.98(18) . . ?
C25 C24 C21 113.84(16) . . ?
C1 C6 C5 119.27(18) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.029
