# 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_q32c
_database_code_depnum_ccdc_archive 'CCDC 1408273'
_audit_update_record             
;
2015-06-22 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXTL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 O2'
_chemical_formula_weight         320.41

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   C2/c

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'
'-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                   19.9651(7)
_cell_length_b                   6.1398(2)
_cell_length_c                   15.2881(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.9270(10)
_cell_angle_gamma                90.00
_cell_volume                     1670.87(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6742
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      68.63

_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_monochromator  'Helios multilayer optics'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7532
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.97
_diffrn_reflns_theta_max         69.35
_reflns_number_total             1507
_reflns_number_gt                1484
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0534P)²+1.3367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1507
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
O O 0.46005(4) -0.21721(13) 0.51105(5) 0.0163(2) Uani 1 1 d . . .
C1 C 0.44137(6) -0.15417(18) 0.41139(8) 0.0155(3) Uani 1 1 d . . .
H1A H 0.4058(7) -0.263(2) 0.3662(10) 0.014(3) Uiso 1 1 d . . .
H1B H 0.4864(7) -0.161(2) 0.4016(9) 0.016(3) Uiso 1 1 d . . .
C2 C 0.40787(6) 0.07128(18) 0.38944(8) 0.0153(3) Uani 1 1 d . . .
C3 C 0.46301(6) 0.25990(18) 0.43211(8) 0.0160(3) Uani 1 1 d . . .
H3 H 0.4444(7) 0.384(2) 0.4531(10) 0.017(3) Uiso 1 1 d . . .
C4 C 0.43164(6) 0.21214(19) 0.32551(8) 0.0186(3) Uani 1 1 d . . .
H4A H 0.3951(8) 0.313(2) 0.2791(10) 0.022(3) Uiso 1 1 d . . .
H4B H 0.4656(8) 0.144(2) 0.3067(10) 0.019(3) Uiso 1 1 d . . .
C5 C 0.33068(6) 0.10014(18) 0.38176(7) 0.0153(3) Uani 1 1 d . . .
C6 C 0.29101(6) 0.29565(19) 0.34873(8) 0.0179(3) Uani 1 1 d . . .
H6 H 0.3122(8) 0.414(2) 0.3278(10) 0.021(3) Uiso 1 1 d . . .
C7 C 0.22037(6) 0.3230(2) 0.34426(8) 0.0194(3) Uani 1 1 d . . .
H7 H 0.1951(8) 0.457(3) 0.3220(10) 0.023(3) Uiso 1 1 d . . .
C8 C 0.18610(6) 0.1569(2) 0.37146(8) 0.0186(3) Uani 1 1 d . . .
C9 C 0.22526(6) -0.0382(2) 0.40376(8) 0.0187(3) Uani 1 1 d . . .
H9 H 0.2028(8) -0.157(2) 0.4227(10) 0.021(3) Uiso 1 1 d . . .
C10 C 0.29632(6) -0.06623(19) 0.40934(8) 0.0171(3) Uani 1 1 d . . .
H10 H 0.3228(8) -0.204(2) 0.4327(10) 0.021(3) Uiso 1 1 d . . .
C11 C 0.10949(7) 0.1880(2) 0.36648(9) 0.0248(3) Uani 1 1 d . . .
H11A H 0.0956(11) 0.069(4) 0.3960(15) 0.061(6) Uiso 1 1 d . . .
H11B H 0.0714(12) 0.197(3) 0.2994(15) 0.058(6) Uiso 1 1 d . . .
H11C H 0.1086(12) 0.315(4) 0.4037(16) 0.064(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O 0.0119(4) 0.0171(4) 0.0177(4) 0.0027(3) 0.0049(3) 0.0006(3)
C1 0.0135(5) 0.0154(6) 0.0167(5) -0.0009(4) 0.0059(4) -0.0001(4)
C2 0.0134(5) 0.0160(6) 0.0149(5) 0.0003(4) 0.0050(4) -0.0003(4)
C3 0.0117(5) 0.0141(6) 0.0202(6) 0.0020(4) 0.0054(4) 0.0006(4)
C4 0.0152(6) 0.0208(6) 0.0195(6) 0.0039(5) 0.0076(5) 0.0009(4)
C5 0.0130(5) 0.0177(6) 0.0126(5) -0.0020(4) 0.0035(4) -0.0002(4)
C6 0.0166(5) 0.0172(6) 0.0176(5) 0.0006(4) 0.0057(4) -0.0003(4)
C7 0.0168(6) 0.0196(6) 0.0179(5) -0.0003(4) 0.0044(4) 0.0047(4)
C8 0.0138(6) 0.0263(6) 0.0134(5) -0.0035(4) 0.0042(4) 0.0009(4)
C9 0.0164(5) 0.0228(6) 0.0161(5) -0.0002(4) 0.0066(4) -0.0025(4)
C10 0.0156(5) 0.0171(6) 0.0162(5) 0.0003(4) 0.0050(4) 0.0007(4)
C11 0.0161(6) 0.0354(8) 0.0225(6) -0.0015(5) 0.0084(5) 0.0030(5)

_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
O C3 1.4053(13) 5_656 ?
O C1 1.4477(13) . ?
C1 C2 1.5076(15) . ?
C1 H1A 0.991(13) . ?
C1 H1B 0.977(14) . ?
C2 C5 1.5020(14) . ?
C2 C3 1.5258(15) . ?
C2 C4 1.5325(15) . ?
C3 O 1.4053(13) 5_656 ?
C3 C4 1.4866(15) . ?
C3 H3 0.965(15) . ?
C4 H4A 0.974(15) . ?
C4 H4B 0.946(15) . ?
C5 C10 1.3978(16) . ?
C5 C6 1.4004(16) . ?
C6 C7 1.3907(16) . ?
C6 H6 0.964(15) . ?
C7 C8 1.3922(18) . ?
C7 H7 0.942(16) . ?
C8 C9 1.3930(17) . ?
C8 C11 1.5088(15) . ?
C9 C10 1.3928(16) . ?
C9 H9 0.965(15) . ?
C10 H10 0.975(15) . ?
C11 H11A 0.96(2) . ?
C11 H11B 0.96(2) . ?
C11 H11C 0.97(2) . ?

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
C3 O C1 112.89(8) 5_656 . ?
O C1 C2 110.89(9) . . ?
O C1 H1A 108.4(8) . . ?
C2 C1 H1A 110.9(7) . . ?
O C1 H1B 109.4(7) . . ?
C2 C1 H1B 110.7(8) . . ?
H1A C1 H1B 106.4(11) . . ?
C5 C2 C1 117.50(9) . . ?
C5 C2 C3 117.38(9) . . ?
C1 C2 C3 116.12(9) . . ?
C5 C2 C4 119.12(9) . . ?
C1 C2 C4 115.20(9) . . ?
C3 C2 C4 58.17(7) . . ?
O C3 C4 116.16(10) 5_656 . ?
O C3 C2 119.86(9) 5_656 . ?
C4 C3 C2 61.14(7) . . ?
O C3 H3 114.8(8) 5_656 . ?
C4 C3 H3 119.1(8) . . ?
C2 C3 H3 115.5(8) . . ?
C3 C4 C2 60.69(7) . . ?
C3 C4 H4A 118.6(8) . . ?
C2 C4 H4A 118.5(9) . . ?
C3 C4 H4B 114.7(8) . . ?
C2 C4 H4B 114.5(8) . . ?
H4A C4 H4B 117.6(12) . . ?
C10 C5 C6 117.41(10) . . ?
C10 C5 C2 121.10(10) . . ?
C6 C5 C2 121.48(10) . . ?
C7 C6 C5 121.10(11) . . ?
C7 C6 H6 118.7(8) . . ?
C5 C6 H6 120.2(8) . . ?
C6 C7 C8 121.44(11) . . ?
C6 C7 H7 119.2(9) . . ?
C8 C7 H7 119.4(9) . . ?
C7 C8 C9 117.56(10) . . ?
C7 C8 C11 121.10(11) . . ?
C9 C8 C11 121.33(11) . . ?
C10 C9 C8 121.37(11) . . ?
C10 C9 H9 119.1(8) . . ?
C8 C9 H9 119.5(8) . . ?
C9 C10 C5 121.11(10) . . ?
C9 C10 H10 119.9(8) . . ?
C5 C10 H10 119.0(8) . . ?
C8 C11 H11A 112.4(12) . . ?
C8 C11 H11B 110.8(12) . . ?
H11A C11 H11B 106.6(17) . . ?
C8 C11 H11C 111.0(12) . . ?
H11A C11 H11C 104.5(17) . . ?
H11B C11 H11C 111.3(17) . . ?

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
C3 O C1 C2 -119.27(9) 5_656 . . . ?
O C1 C2 C5 -69.90(11) . . . . ?
O C1 C2 C3 76.48(11) . . . . ?
O C1 C2 C4 141.74(9) . . . . ?
C5 C2 C3 O 145.81(10) . . . 5_656 ?
C1 C2 C3 O -0.62(14) . . . 5_656 ?
C4 C2 C3 O -105.32(11) . . . 5_656 ?
C5 C2 C3 C4 -108.87(11) . . . . ?
C1 C2 C3 C4 104.70(11) . . . . ?
O C3 C4 C2 111.26(11) 5_656 . . . ?
C5 C2 C4 C3 105.89(11) . . . . ?
C1 C2 C4 C3 -106.29(10) . . . . ?
C1 C2 C5 C10 10.09(15) . . . . ?
C3 C2 C5 C10 -135.87(11) . . . . ?
C4 C2 C5 C10 157.18(10) . . . . ?
C1 C2 C5 C6 -171.26(10) . . . . ?
C3 C2 C5 C6 42.79(14) . . . . ?
C4 C2 C5 C6 -24.17(15) . . . . ?
C10 C5 C6 C7 0.39(16) . . . . ?
C2 C5 C6 C7 -178.31(10) . . . . ?
C5 C6 C7 C8 -0.61(17) . . . . ?
C6 C7 C8 C9 0.20(17) . . . . ?
C6 C7 C8 C11 179.94(10) . . . . ?
C7 C8 C9 C10 0.41(16) . . . . ?
C11 C8 C9 C10 -179.32(10) . . . . ?
C8 C9 C10 C5 -0.63(17) . . . . ?
C6 C5 C10 C9 0.22(16) . . . . ?
C2 C5 C10 C9 178.92(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.959
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.039
