# 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_at63m
_database_code_depnum_ccdc_archive 'CCDC 1032788'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2015-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4a-hydroxy 3,3-dimethy-l 2,3,4,4a-tetrhydro-1H-benzo[b]xanthen-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 O3'
_chemical_formula_sum            'C19 H18 O3'
_chemical_formula_weight         294.33

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   11.6133(8)
_cell_length_b                   6.8128(5)
_cell_length_c                   20.3843(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.514(3)
_cell_angle_gamma                90.00
_cell_volume                     1529.32(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3771
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9814
_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            11536
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2685
_reflns_number_gt                2392
_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)+(0.0544P)²+0.6474P] 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         2685
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 -0.0674(2) 0.6501(4) 0.78531(11) 0.0621(6) Uani 1 1 d . . .
H1 H -0.0142 0.7533 0.8031 0.075 Uiso 1 1 calc R . .
C2 C -0.1501(2) 0.6649(4) 0.72062(12) 0.0769(8) Uani 1 1 d . . .
H2 H -0.1534 0.7795 0.6953 0.092 Uiso 1 1 calc R . .
C3 C -0.2292(2) 0.5121(5) 0.69193(13) 0.0824(8) Uani 1 1 d . . .
H3 H -0.2838 0.5237 0.6475 0.099 Uiso 1 1 calc R . .
C4 C -0.2265(2) 0.3464(4) 0.72885(12) 0.0722(7) Uani 1 1 d . . .
H4 H -0.2797 0.2445 0.7094 0.087 Uiso 1 1 calc R . .
C5 C -0.14466(19) 0.3249(3) 0.79633(11) 0.0567(5) Uani 1 1 d . . .
C6 C -0.06231(18) 0.4789(3) 0.82541(10) 0.0495(5) Uani 1 1 d . . .
C7 C 0.02437(17) 0.4524(3) 0.89299(9) 0.0453(5) Uani 1 1 d . . .
C8 C 0.02185(18) 0.2790(3) 0.92760(10) 0.0483(5) Uani 1 1 d . . .
C9 C -0.0632(2) 0.1312(3) 0.90010(12) 0.0607(6) Uani 1 1 d . . .
H9 H -0.0648 0.0188 0.9257 0.073 Uiso 1 1 calc R . .
C10 C -0.1431(2) 0.1533(3) 0.83577(12) 0.0635(6) Uani 1 1 d . . .
H10 H -0.1984 0.0535 0.8170 0.076 Uiso 1 1 calc R . .
C11 C 0.11418(18) 0.5949(3) 0.92844(10) 0.0471(5) Uani 1 1 d . . .
H11 H 0.1078 0.7233 0.9122 0.056 Uiso 1 1 calc R . .
C12 C 0.20664(17) 0.5456(3) 0.98441(10) 0.0445(5) Uani 1 1 d . . .
C13 C 0.22047(18) 0.3328(3) 1.00582(10) 0.0440(5) Uani 1 1 d . . .
C14 C 0.28387(19) 0.3014(3) 1.08213(10) 0.0507(5) Uani 1 1 d . . .
H14A H 0.3020 0.1628 1.0901 0.061 Uiso 1 1 calc R . .
H14B H 0.2288 0.3376 1.1073 0.061 Uiso 1 1 calc R . .
C15 C 0.40164(19) 0.4179(3) 1.11140(10) 0.0528(5) Uani 1 1 d . . .
C16 C 0.4998(2) 0.3515(4) 1.08137(12) 0.0651(6) Uani 1 1 d . . .
H16A H 0.5144 0.2136 1.0896 0.098 Uiso 1 1 calc R . .
H16B H 0.5733 0.4229 1.1031 0.098 Uiso 1 1 calc R . .
H16C H 0.4735 0.3761 1.0325 0.098 Uiso 1 1 calc R . .
C17 C 0.4489(2) 0.3879(4) 1.19003(11) 0.0780(7) Uani 1 1 d . . .
H17A H 0.4694 0.2522 1.2001 0.117 Uiso 1 1 calc R . .
H17B H 0.3872 0.4252 1.2097 0.117 Uiso 1 1 calc R . .
H17C H 0.5198 0.4674 1.2096 0.117 Uiso 1 1 calc R . .
C18 C 0.3734(2) 0.6360(3) 1.09607(12) 0.0691(7) Uani 1 1 d . . .
H18A H 0.3330 0.6842 1.1279 0.083 Uiso 1 1 calc R . .
H18B H 0.4499 0.7058 1.1062 0.083 Uiso 1 1 calc R . .
C19 C 0.29647(19) 0.6892(3) 1.02388(11) 0.0540(5) Uani 1 1 d . . .
O1 O 0.10145(12) 0.24548(19) 0.99218(7) 0.0535(4) Uani 1 1 d . . .
O2 O 0.27808(13) 0.2413(2) 0.96343(7) 0.0501(4) Uani 1 1 d . . .
O3 O 0.30530(15) 0.8504(2) 1.00021(9) 0.0764(5) Uani 1 1 d . . .
H2O H 0.294(2) 0.117(4) 0.9783(12) 0.080(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.366(3) . ?
C1 C6 1.415(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C5 C10 1.416(3) . ?
C6 C7 1.436(3) . ?
C7 C8 1.381(3) . ?
C7 C11 1.440(3) . ?
C8 O1 1.366(2) . ?
C8 C9 1.397(3) . ?
C9 C10 1.353(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.338(3) . ?
C11 H11 0.9300 . ?
C12 C19 1.469(3) . ?
C12 C13 1.508(2) . ?
C13 O2 1.397(2) . ?
C13 O1 1.449(2) . ?
C13 C14 1.510(3) . ?
C14 C15 1.529(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.524(3) . ?
C15 C18 1.532(3) . ?
C15 C17 1.534(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.503(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O3 1.217(2) . ?
O2 H2O 0.90(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
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 121.3(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C10 121.5(2) . . ?
C6 C5 C10 119.27(19) . . ?
C5 C6 C1 118.04(19) . . ?
C5 C6 C7 118.88(18) . . ?
C1 C6 C7 123.1(2) . . ?
C8 C7 C6 118.37(18) . . ?
C8 C7 C11 116.74(17) . . ?
C6 C7 C11 124.89(17) . . ?
O1 C8 C7 121.16(18) . . ?
O1 C8 C9 116.22(17) . . ?
C7 C8 C9 122.59(19) . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C5 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
C12 C11 C7 121.06(17) . . ?
C12 C11 H11 119.5 . . ?
C7 C11 H11 119.5 . . ?
C11 C12 C19 122.52(17) . . ?
C11 C12 C13 118.12(17) . . ?
C19 C12 C13 119.32(17) . . ?
O2 C13 O1 108.25(15) . . ?
O2 C13 C12 106.15(15) . . ?
O1 C13 C12 109.39(15) . . ?
O2 C13 C14 113.67(16) . . ?
O1 C13 C14 105.25(14) . . ?
C12 C13 C14 114.00(16) . . ?
C13 C14 C15 114.31(16) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C18 110.19(19) . . ?
C16 C15 C14 112.31(18) . . ?
C18 C15 C14 108.45(17) . . ?
C16 C15 C17 108.34(18) . . ?
C18 C15 C17 108.97(19) . . ?
C14 C15 C17 108.52(18) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C15 117.10(18) . . ?
C19 C18 H18A 108.0 . . ?
C15 C18 H18A 108.0 . . ?
C19 C18 H18B 108.0 . . ?
C15 C18 H18B 108.0 . . ?
H18A C18 H18B 107.3 . . ?
O3 C19 C12 121.2(2) . . ?
O3 C19 C18 120.5(2) . . ?
C12 C19 C18 118.25(18) . . ?
C8 O1 C13 115.39(14) . . ?
C13 O2 H2O 107.4(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
C6 C1 C2 C3 -1.3(4) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 C10 178.7(2) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C10 C5 C6 C1 -178.84(19) . . . . ?
C4 C5 C6 C7 -177.30(19) . . . . ?
C10 C5 C6 C7 2.9(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 178.4(2) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C1 C6 C7 C8 -179.68(18) . . . . ?
C5 C6 C7 C11 179.19(18) . . . . ?
C1 C6 C7 C11 1.0(3) . . . . ?
C6 C7 C8 O1 -179.62(16) . . . . ?
C11 C7 C8 O1 -0.3(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C11 C7 C8 C9 177.86(19) . . . . ?
O1 C8 C9 C10 -178.70(19) . . . . ?
C7 C8 C9 C10 3.1(3) . . . . ?
C8 C9 C10 C5 -1.6(4) . . . . ?
C4 C5 C10 C9 178.8(2) . . . . ?
C6 C5 C10 C9 -1.4(3) . . . . ?
C8 C7 C11 C12 14.4(3) . . . . ?
C6 C7 C11 C12 -166.31(18) . . . . ?
C7 C11 C12 C19 -176.89(17) . . . . ?
C7 C11 C12 C13 5.2(3) . . . . ?
C11 C12 C13 O2 80.9(2) . . . . ?
C19 C12 C13 O2 -97.10(19) . . . . ?
C11 C12 C13 O1 -35.7(2) . . . . ?
C19 C12 C13 O1 146.31(17) . . . . ?
C11 C12 C13 C14 -153.21(17) . . . . ?
C19 C12 C13 C14 28.8(2) . . . . ?
O2 C13 C14 C15 73.5(2) . . . . ?
O1 C13 C14 C15 -168.20(15) . . . . ?
C12 C13 C14 C15 -48.3(2) . . . . ?
C13 C14 C15 C16 -65.8(2) . . . . ?
C13 C14 C15 C18 56.2(2) . . . . ?
C13 C14 C15 C17 174.46(17) . . . . ?
C16 C15 C18 C19 76.8(3) . . . . ?
C14 C15 C18 C19 -46.5(3) . . . . ?
C17 C15 C18 C19 -164.5(2) . . . . ?
C11 C12 C19 O3 -14.6(3) . . . . ?
C13 C12 C19 O3 163.26(19) . . . . ?
C11 C12 C19 C18 162.26(19) . . . . ?
C13 C12 C19 C18 -19.8(3) . . . . ?
C15 C18 C19 O3 -153.3(2) . . . . ?
C15 C18 C19 C12 29.8(3) . . . . ?
C7 C8 O1 C13 -32.9(2) . . . . ?
C9 C8 O1 C13 148.85(18) . . . . ?
O2 C13 O1 C8 -66.26(19) . . . . ?
C12 C13 O1 C8 49.0(2) . . . . ?
C14 C13 O1 C8 171.86(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
