# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_ab_1
_database_code_depnum_ccdc_archive 'CCDC 1412809'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 O2'
_chemical_formula_sum            'C17 H20 O2'
_chemical_formula_weight         256.33

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.7321(3)
_cell_length_b                   9.3720(4)
_cell_length_c                   11.4758(5)
_cell_angle_alpha                95.498(3)
_cell_angle_beta                 99.490(3)
_cell_angle_gamma                104.725(3)
_cell_volume                     683.45(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            9260
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2348
_reflns_number_gt                1909
_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)+(0.0573P)²+0.1050P] 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_number_reflns         2348
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C8 C 0.0481(2) 0.71578(14) 0.50746(12) 0.0355(3) Uani 1 1 d . . .
C6 C -0.1918(2) 0.57059(14) 0.32772(12) 0.0390(3) Uani 1 1 d . . .
C1 C -0.0242(2) 0.55335(15) 0.27799(12) 0.0401(3) Uani 1 1 d . . .
C7 C -0.1491(2) 0.65681(14) 0.44480(12) 0.0387(3) Uani 1 1 d . . .
H7 H -0.2605 0.6721 0.4779 0.046 Uiso 1 1 calc R . .
C10 C 0.1099(2) 0.81575(14) 0.62737(11) 0.0367(3) Uani 1 1 d . . .
H10 H 0.2024 0.7745 0.6812 0.044 Uiso 1 1 calc R . .
C9 C 0.2220(2) 0.68489(15) 0.45764(12) 0.0407(3) Uani 1 1 d . . .
C5 C -0.3941(2) 0.50595(16) 0.26026(14) 0.0492(4) Uani 1 1 d . . .
H5 H -0.5096 0.5150 0.2919 0.059 Uiso 1 1 calc R . .
C2 C -0.0517(3) 0.47838(17) 0.16396(14) 0.0532(4) Uani 1 1 d . . .
H2 H 0.0633 0.4700 0.1314 0.064 Uiso 1 1 calc R . .
C17 C 0.2377(2) 0.97426(15) 0.61192(12) 0.0428(4) Uani 1 1 d . . .
H17A H 0.2757 0.9687 0.5340 0.051 Uiso 1 1 calc R . .
H17B H 0.1477 1.0402 0.6129 0.051 Uiso 1 1 calc R . .
C11 C -0.0817(2) 0.81659(16) 0.68247(12) 0.0430(4) Uani 1 1 d . . .
H11A H -0.1602 0.7137 0.6799 0.052 Uiso 1 1 calc R . .
H11B H -0.1697 0.8621 0.6312 0.052 Uiso 1 1 calc R . .
C3 C -0.2524(3) 0.41640(18) 0.09969(14) 0.0579(4) Uani 1 1 d . . .
H3 H -0.2730 0.3654 0.0232 0.069 Uiso 1 1 calc R . .
C4 C -0.4234(3) 0.42910(17) 0.14752(14) 0.0554(4) Uani 1 1 d . . .
H4 H -0.5582 0.3858 0.1036 0.066 Uiso 1 1 calc R . .
C16 C 0.4371(2) 1.04383(18) 0.70609(14) 0.0545(4) Uani 1 1 d . . .
H16A H 0.5422 0.9949 0.6893 0.065 Uiso 1 1 calc R . .
H16B H 0.4883 1.1477 0.6965 0.065 Uiso 1 1 calc R . .
C12 C -0.0487(3) 0.89499(17) 0.81053(14) 0.0526(4) Uani 1 1 d . . .
H12A H -0.1829 0.8723 0.8353 0.063 Uiso 1 1 calc R . .
H12B H 0.0427 0.8520 0.8620 0.063 Uiso 1 1 calc R . .
C14 C 0.2790(3) 1.12108(18) 0.88493(14) 0.0587(4) Uani 1 1 d . . .
H14A H 0.3265 1.2243 0.8727 0.070 Uiso 1 1 calc R . .
H14B H 0.2984 1.1198 0.9704 0.070 Uiso 1 1 calc R . .
C15 C 0.4203(3) 1.03741(19) 0.83633(14) 0.0558(4) Uani 1 1 d . . .
H15A H 0.3707 0.9336 0.8463 0.067 Uiso 1 1 calc R . .
H15B H 0.5599 1.0762 0.8849 0.067 Uiso 1 1 calc R . .
C13 C 0.0438(3) 1.06458(18) 0.83265(15) 0.0566(4) Uani 1 1 d . . .
H13A H -0.0302 1.1067 0.8865 0.068 Uiso 1 1 calc R . .
H13B H 0.0170 1.1023 0.7575 0.068 Uiso 1 1 calc R . .
O1 O 0.17791(15) 0.61006(11) 0.34205(9) 0.0471(3) Uani 1 1 d . . .
O2 O 0.40281(16) 0.71910(13) 0.50789(10) 0.0566(3) Uani 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
C8 0.0349(7) 0.0354(7) 0.0386(7) 0.0077(5) 0.0103(6) 0.0111(5)
C6 0.0396(8) 0.0364(7) 0.0418(8) 0.0054(6) 0.0092(6) 0.0112(6)
C1 0.0410(8) 0.0372(7) 0.0425(8) 0.0059(6) 0.0111(6) 0.0094(6)
C7 0.0360(8) 0.0390(7) 0.0428(8) 0.0035(6) 0.0112(6) 0.0119(6)
C10 0.0344(7) 0.0397(7) 0.0359(7) 0.0062(6) 0.0057(6) 0.0105(6)
C9 0.0379(8) 0.0428(7) 0.0425(8) 0.0061(6) 0.0112(6) 0.0111(6)
C5 0.0432(9) 0.0484(8) 0.0517(9) 0.0001(7) 0.0050(7) 0.0102(7)
C2 0.0614(10) 0.0544(9) 0.0463(9) 0.0035(7) 0.0203(8) 0.0157(8)
C17 0.0448(8) 0.0416(8) 0.0401(8) 0.0059(6) 0.0085(6) 0.0082(6)
C11 0.0397(8) 0.0440(8) 0.0441(8) 0.0020(6) 0.0125(6) 0.0083(6)
C3 0.0734(12) 0.0533(9) 0.0410(9) -0.0020(7) 0.0077(8) 0.0125(8)
C4 0.0536(10) 0.0523(9) 0.0508(9) -0.0023(7) -0.0007(8) 0.0084(7)
C16 0.0452(9) 0.0554(9) 0.0533(9) -0.0004(7) 0.0078(7) 0.0012(7)
C12 0.0528(10) 0.0579(9) 0.0478(9) 0.0007(7) 0.0194(7) 0.0127(7)
C14 0.0685(11) 0.0541(9) 0.0447(9) -0.0041(7) 0.0061(8) 0.0086(8)
C15 0.0490(9) 0.0610(10) 0.0467(9) 0.0000(7) -0.0050(7) 0.0079(7)
C13 0.0645(11) 0.0552(9) 0.0508(9) -0.0063(7) 0.0146(8) 0.0207(8)
O1 0.0388(6) 0.0558(6) 0.0475(6) -0.0004(5) 0.0160(5) 0.0124(5)
O2 0.0340(6) 0.0768(8) 0.0578(7) 0.0005(5) 0.0080(5) 0.0175(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
C8 C7 1.3492(18) . ?
C8 C9 1.464(2) . ?
C8 C10 1.5200(18) . ?
C6 C1 1.383(2) . ?
C6 C5 1.4015(19) . ?
C6 C7 1.4448(19) . ?
C1 O1 1.3791(16) . ?
C1 C2 1.385(2) . ?
C10 C11 1.5282(19) . ?
C10 C17 1.5589(18) . ?
C9 O2 1.2050(16) . ?
C9 O1 1.3876(17) . ?
C5 C4 1.377(2) . ?
C2 C3 1.378(2) . ?
C17 C16 1.528(2) . ?
C11 C12 1.533(2) . ?
C3 C4 1.380(2) . ?
C16 C15 1.523(2) . ?
C12 C13 1.531(2) . ?
C14 C15 1.517(2) . ?
C14 C13 1.533(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
C7 C8 C9 118.84(12) . . ?
C7 C8 C10 125.72(12) . . ?
C9 C8 C10 115.44(11) . . ?
C1 C6 C5 117.95(13) . . ?
C1 C6 C7 118.43(13) . . ?
C5 C6 C7 123.61(13) . . ?
O1 C1 C6 120.39(12) . . ?
O1 C1 C2 117.67(13) . . ?
C6 C1 C2 121.94(14) . . ?
C8 C7 C6 121.76(13) . . ?
C8 C10 C11 111.15(11) . . ?
C8 C10 C17 109.24(11) . . ?
C11 C10 C17 113.30(11) . . ?
O2 C9 O1 116.11(12) . . ?
O2 C9 C8 125.88(13) . . ?
O1 C9 C8 118.01(12) . . ?
C4 C5 C6 120.61(15) . . ?
C3 C2 C1 118.75(15) . . ?
C16 C17 C10 115.50(12) . . ?
C10 C11 C12 118.90(12) . . ?
C2 C3 C4 120.80(15) . . ?
C5 C4 C3 119.93(15) . . ?
C15 C16 C17 117.24(13) . . ?
C13 C12 C11 117.14(13) . . ?
C15 C14 C13 117.39(13) . . ?
C14 C15 C16 116.69(14) . . ?
C12 C13 C14 115.86(14) . . ?
C1 O1 C9 122.15(11) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058
