# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_tt
_database_code_depnum_ccdc_archive 'CCDC 1421254'
_audit_update_record             
;
2015-08-29 deposited with the CCDC.
2016-01-28 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 H22 O'
_chemical_formula_weight         278.38

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.4061(12)
_cell_length_b                   8.6026(12)
_cell_length_c                   12.582(2)
_cell_angle_alpha                91.647(5)
_cell_angle_beta                 102.618(5)
_cell_angle_gamma                112.149(4)
_cell_volume                     816.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    0(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    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      0(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  ?
_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            11257
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2801
_reflns_number_gt                2405
_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)+(0.1087P)²+0.2697P] 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       0.147(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
O1 O 0.0052(2) 0.7913(2) 0.81476(14) 0.0779(5) Uani 1 1 d . . .
C1 C -0.1136(4) 0.7139(5) 0.3952(2) 0.1081(11) Uani 1 1 d . . .
H1A H -0.0961 0.8202 0.3637 0.162 Uiso 1 1 calc R . .
H1B H -0.2234 0.6764 0.4200 0.162 Uiso 1 1 calc R . .
H1C H -0.1216 0.6275 0.3395 0.162 Uiso 1 1 calc R . .
C2 C 0.2022(3) 0.7501(3) 0.47527(17) 0.0650(6) Uani 1 1 d . . .
H2 H 0.2132 0.7382 0.4022 0.078 Uiso 1 1 calc R . .
C3 C 0.0414(3) 0.7411(3) 0.49168(18) 0.0679(6) Uani 1 1 d . . .
C4 C 0.0275(3) 0.7567(3) 0.59809(17) 0.0602(5) Uani 1 1 d . . .
H4 H -0.0819 0.7497 0.6112 0.072 Uiso 1 1 calc R . .
C5 C 0.1704(2) 0.7825(2) 0.68705(14) 0.0458(5) Uani 1 1 d . . .
C6 C 0.3331(2) 0.79252(19) 0.66964(14) 0.0426(4) Uani 1 1 d . . .
C7 C 0.3478(3) 0.7758(2) 0.56154(16) 0.0529(5) Uani 1 1 d . . .
C8 C 0.5180(3) 0.7833(4) 0.53723(19) 0.0749(7) Uani 1 1 d . . .
H8A H 0.5092 0.7866 0.4584 0.112 Uiso 1 1 calc R . .
H8B H 0.5390 0.6829 0.5592 0.112 Uiso 1 1 calc R . .
H8C H 0.6166 0.8851 0.5782 0.112 Uiso 1 1 calc R . .
C9 C 0.1464(3) 0.7994(2) 0.79951(16) 0.0521(5) Uani 1 1 d . . .
C10 C 0.3014(3) 0.8289(3) 0.89468(15) 0.0578(5) Uani 1 1 d . . .
H10A H 0.2574 0.7768 0.9573 0.069 Uiso 1 1 calc R . .
H10B H 0.3660 0.9521 0.9175 0.069 Uiso 1 1 calc R . .
C11 C 0.4277(3) 0.7563(2) 0.86753(16) 0.0557(5) Uani 1 1 d . . .
H11A H 0.3680 0.6314 0.8541 0.067 Uiso 1 1 calc R . .
H11B H 0.5319 0.7864 0.9308 0.067 Uiso 1 1 calc R . .
C12 C 0.4897(2) 0.8235(2) 0.76575(14) 0.0431(4) Uani 1 1 d . . .
H12 H 0.5564 0.7574 0.7452 0.052 Uiso 1 1 calc R . .
C13 C 0.6182(2) 1.0084(2) 0.79194(13) 0.0396(4) Uani 1 1 d . . .
C14 C 0.5613(2) 1.1403(2) 0.77599(13) 0.0435(4) Uani 1 1 d . . .
H14 H 0.4397 1.1156 0.7442 0.052 Uiso 1 1 calc R . .
C15 C 0.6797(2) 1.3077(2) 0.80583(15) 0.0492(5) Uani 1 1 d . . .
C16 C 0.8574(2) 1.3424(2) 0.85127(14) 0.0499(5) Uani 1 1 d . . .
H16 H 0.9389 1.4566 0.8719 0.060 Uiso 1 1 calc R . .
C17 C 0.9180(2) 1.2137(2) 0.86711(14) 0.0481(5) Uani 1 1 d . . .
C18 C 0.7968(2) 1.0477(2) 0.83718(14) 0.0455(4) Uani 1 1 d . . .
H18 H 0.8371 0.9586 0.8479 0.055 Uiso 1 1 calc R . .
C19 C 0.6151(3) 1.4484(3) 0.7882(2) 0.0779(7) Uani 1 1 d . . .
H19A H 0.5051 1.4084 0.7300 0.117 Uiso 1 1 calc R . .
H19B H 0.7053 1.5445 0.7667 0.117 Uiso 1 1 calc R . .
H19C H 0.5930 1.4839 0.8563 0.117 Uiso 1 1 calc R . .
C20 C 1.1105(3) 1.2518(3) 0.91845(19) 0.0682(6) Uani 1 1 d . . .
H20A H 1.1815 1.3716 0.9170 0.102 Uiso 1 1 calc R . .
H20B H 1.1509 1.1819 0.8771 0.102 Uiso 1 1 calc R . .
H20C H 1.1243 1.2268 0.9946 0.102 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
O1 C9 1.219(2) . ?
C1 C3 1.513(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.385(3) . ?
C2 C7 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(2) . ?
C5 C9 1.483(3) . ?
C6 C7 1.400(3) . ?
C6 C12 1.512(2) . ?
C7 C8 1.506(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.499(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.534(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(2) . ?
C12 H12 1.0000 . ?
C13 C18 1.387(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 C19 1.505(3) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 C20 1.508(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 122.47(19) . . ?
C3 C2 H2 118.8 . . ?
C7 C2 H2 118.8 . . ?
C4 C3 C2 117.87(19) . . ?
C4 C3 C1 121.4(2) . . ?
C2 C3 C1 120.7(2) . . ?
C3 C4 C5 121.50(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 120.24(17) . . ?
C4 C5 C9 118.59(17) . . ?
C6 C5 C9 121.17(16) . . ?
C7 C6 C5 118.54(17) . . ?
C7 C6 C12 120.91(16) . . ?
C5 C6 C12 120.55(15) . . ?
C2 C7 C6 119.39(18) . . ?
C2 C7 C8 119.42(18) . . ?
C6 C7 C8 121.19(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C5 121.25(19) . . ?
O1 C9 C10 120.55(18) . . ?
C5 C9 C10 118.20(16) . . ?
C9 C10 C11 112.46(16) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 111.24(15) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C6 C12 C13 113.23(13) . . ?
C6 C12 C11 110.89(14) . . ?
C13 C12 C11 110.80(14) . . ?
C6 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
C18 C13 C14 118.48(15) . . ?
C18 C13 C12 119.40(14) . . ?
C14 C13 C12 122.07(14) . . ?
C15 C14 C13 120.98(15) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 118.97(16) . . ?
C16 C15 C19 120.97(17) . . ?
C14 C15 C19 120.06(17) . . ?
C17 C16 C15 121.31(16) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 118.52(16) . . ?
C16 C17 C20 121.10(17) . . ?
C18 C17 C20 120.36(17) . . ?
C17 C18 C13 121.74(15) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C7 C2 C3 C4 -0.7(3) . . . . ?
C7 C2 C3 C1 179.6(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C1 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 C9 179.59(19) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C9 C5 C6 C7 -179.92(15) . . . . ?
C4 C5 C6 C12 178.93(15) . . . . ?
C9 C5 C6 C12 -0.9(2) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
C3 C2 C7 C8 179.7(2) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C12 C6 C7 C2 -178.99(16) . . . . ?
C5 C6 C7 C8 -179.27(17) . . . . ?
C12 C6 C7 C8 1.7(3) . . . . ?
C4 C5 C9 O1 -0.1(3) . . . . ?
C6 C5 C9 O1 179.77(17) . . . . ?
C4 C5 C9 C10 -179.39(17) . . . . ?
C6 C5 C9 C10 0.5(3) . . . . ?
O1 C9 C10 C11 152.99(18) . . . . ?
C5 C9 C10 C11 -27.7(2) . . . . ?
C9 C10 C11 C12 54.8(2) . . . . ?
C7 C6 C12 C13 81.49(19) . . . . ?
C5 C6 C12 C13 -97.49(18) . . . . ?
C7 C6 C12 C11 -153.24(16) . . . . ?
C5 C6 C12 C11 27.8(2) . . . . ?
C10 C11 C12 C6 -54.4(2) . . . . ?
C10 C11 C12 C13 72.2(2) . . . . ?
C6 C12 C13 C18 -149.89(15) . . . . ?
C11 C12 C13 C18 84.79(18) . . . . ?
C6 C12 C13 C14 32.7(2) . . . . ?
C11 C12 C13 C14 -92.61(18) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C15 176.62(15) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C13 C14 C15 C19 -179.80(18) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C19 C15 C16 C17 -179.56(19) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C15 C16 C17 C20 -178.84(18) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C20 C17 C18 C13 178.60(17) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
C12 C13 C18 C17 -177.07(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
