# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xb9248_0m
_database_code_depnum_ccdc_archive 'CCDC 1532210'
_audit_update_record             
;
2017-02-11 deposited with the CCDC.
2017-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42

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

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

_cell_length_a                   9.968(2)
_cell_length_b                   10.431(3)
_cell_length_c                   10.921(3)
_cell_angle_alpha                62.684(4)
_cell_angle_beta                 78.845(4)
_cell_angle_gamma                62.833(3)
_cell_volume                     897.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1313
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.40

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4521
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3158
_reflns_number_gt                2215
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0677P)²+0.0843P] 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         3158
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.44881(19) 0.6571(2) 0.82281(17) 0.0827(5) Uani 1 1 d . . .
C1 C 0.2901(3) 0.2373(3) 0.9330(2) 0.0851(8) Uani 1 1 d . . .
H1A H 0.2865 0.1368 0.9925 0.128 Uiso 1 1 calc R . .
H1B H 0.1921 0.3219 0.9270 0.128 Uiso 1 1 calc R . .
H1C H 0.3616 0.2492 0.9698 0.128 Uiso 1 1 calc R . .
C2 C 0.3373(2) 0.2434(2) 0.7916(2) 0.0576(5) Uani 1 1 d . . .
C3 C 0.4037(2) 0.1031(2) 0.7736(3) 0.0748(7) Uani 1 1 d . . .
H3 H 0.4207 0.0071 0.8505 0.090 Uiso 1 1 calc R . .
C4 C 0.4450(2) 0.1015(3) 0.6467(3) 0.0795(7) Uani 1 1 d . . .
H4 H 0.4893 0.0059 0.6382 0.095 Uiso 1 1 calc R . .
C5 C 0.4202(2) 0.2418(3) 0.5332(3) 0.0724(6) Uani 1 1 d . . .
H5 H 0.4470 0.2423 0.4466 0.087 Uiso 1 1 calc R . .
C6 C 0.3555(2) 0.3824(2) 0.5471(2) 0.0585(5) Uani 1 1 d . . .
H6 H 0.3386 0.4772 0.4688 0.070 Uiso 1 1 calc R . .
C7 C 0.31461(19) 0.3869(2) 0.67502(19) 0.0473(4) Uani 1 1 d . . .
C8 C 0.24638(19) 0.53905(19) 0.68997(17) 0.0440(4) Uani 1 1 d . . .
C9 C 0.2996(2) 0.5731(2) 0.76841(17) 0.0479(5) Uani 1 1 d . . .
C10 C 0.4486(2) 0.5144(3) 0.8316(2) 0.0669(6) Uani 1 1 d . . .
H10A H 0.4566 0.4370 0.9267 0.080 Uiso 1 1 calc R . .
H10B H 0.5311 0.4666 0.7804 0.080 Uiso 1 1 calc R . .
C11 C 0.3077(3) 0.7917(3) 0.7673(2) 0.0732(6) Uani 1 1 d . . .
H11A H 0.3177 0.8570 0.6712 0.088 Uiso 1 1 calc R . .
H11B H 0.2746 0.8564 0.8181 0.088 Uiso 1 1 calc R . .
C12 C 0.1956(2) 0.7244(2) 0.78172(19) 0.0528(5) Uani 1 1 d . . .
C13 C 0.0808(2) 0.8081(2) 0.6639(2) 0.0595(5) Uani 1 1 d . . .
H13A H 0.1031 0.8904 0.5859 0.071 Uiso 1 1 calc R . .
H13B H -0.0204 0.8570 0.6940 0.071 Uiso 1 1 calc R . .
C14 C 0.09304(19) 0.6783(2) 0.62224(18) 0.0475(5) Uani 1 1 d . . .
C15 C 0.10052(19) 0.73943(19) 0.46440(18) 0.0439(4) Uani 1 1 d . . .
C16 C 0.2176(2) 0.7826(2) 0.39660(19) 0.0524(5) Uani 1 1 d . . .
H16 H 0.2878 0.7744 0.4479 0.063 Uiso 1 1 calc R . .
C17 C 0.2315(2) 0.8371(2) 0.2559(2) 0.0589(5) Uani 1 1 d . . .
H17 H 0.3106 0.8649 0.2135 0.071 Uiso 1 1 calc R . .
C18 C 0.1292(3) 0.8506(2) 0.1780(2) 0.0659(6) Uani 1 1 d . . .
H18 H 0.1388 0.8865 0.0829 0.079 Uiso 1 1 calc R . .
C19 C 0.0124(3) 0.8105(3) 0.2422(2) 0.0696(6) Uani 1 1 d . . .
H19 H -0.0580 0.8201 0.1900 0.084 Uiso 1 1 calc R . .
C20 C -0.0022(2) 0.7560(2) 0.3837(2) 0.0565(5) Uani 1 1 d . . .
H20 H -0.0825 0.7300 0.4251 0.068 Uiso 1 1 calc R . .
C21 C 0.1238(3) 0.6895(3) 0.9241(2) 0.0750(7) Uani 1 1 d . . .
H21A H 0.0674 0.6304 0.9372 0.113 Uiso 1 1 calc R . .
H21B H 0.0575 0.7879 0.9303 0.113 Uiso 1 1 calc R . .
H21C H 0.2015 0.6283 0.9941 0.113 Uiso 1 1 calc R . .
C22 C -0.0304(2) 0.6202(3) 0.6783(2) 0.0628(6) Uani 1 1 d . . .
H22 H -0.0114 0.5256 0.6755 0.075 Uiso 1 1 calc R . .
C23 C -0.1591(3) 0.6845(4) 0.7298(3) 0.0937(8) Uani 1 1 d . . .
H23A H -0.1853 0.7792 0.7357 0.112 Uiso 1 1 calc R . .
H23B H -0.2250 0.6357 0.7607 0.112 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 C11 1.436(3) . ?
O1 C10 1.448(2) . ?
C1 C2 1.505(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.396(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.489(2) . ?
C8 C9 1.330(2) . ?
C8 C14 1.555(2) . ?
C9 C10 1.495(3) . ?
C9 C12 1.498(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C21 1.533(3) . ?
C12 C13 1.535(3) . ?
C13 C14 1.564(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C22 1.519(3) . ?
C14 C15 1.539(2) . ?
C15 C20 1.380(2) . ?
C15 C16 1.397(3) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.301(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?

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
C11 O1 C10 110.86(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.1(2) . . ?
C3 C2 C1 119.73(19) . . ?
C7 C2 C1 122.19(18) . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 118.37(18) . . ?
C6 C7 C8 121.82(16) . . ?
C2 C7 C8 119.80(17) . . ?
C9 C8 C7 126.28(16) . . ?
C9 C8 C14 109.88(16) . . ?
C7 C8 C14 123.71(15) . . ?
C8 C9 C10 136.52(18) . . ?
C8 C9 C12 114.84(16) . . ?
C10 C9 C12 107.75(16) . . ?
O1 C10 C9 103.51(16) . . ?
O1 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
O1 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
O1 C11 C12 106.22(16) . . ?
O1 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
O1 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C9 C12 C11 100.00(16) . . ?
C9 C12 C21 110.91(16) . . ?
C11 C12 C21 110.85(17) . . ?
C9 C12 C13 102.33(14) . . ?
C11 C12 C13 118.29(17) . . ?
C21 C12 C13 113.11(18) . . ?
C12 C13 C14 107.13(15) . . ?
C12 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
C12 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C22 C14 C15 110.93(15) . . ?
C22 C14 C8 108.85(14) . . ?
C15 C14 C8 110.18(14) . . ?
C22 C14 C13 114.56(16) . . ?
C15 C14 C13 109.67(14) . . ?
C8 C14 C13 102.30(14) . . ?
C20 C15 C16 117.03(17) . . ?
C20 C15 C14 124.26(16) . . ?
C16 C15 C14 118.70(15) . . ?
C17 C16 C15 121.71(17) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C16 120.24(19) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.87(19) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 121.09(19) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C14 128.9(2) . . ?
C23 C22 H22 115.5 . . ?
C14 C22 H22 115.5 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?

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 -0.9(3) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C5 C6 C7 C8 179.24(18) . . . . ?
C3 C2 C7 C6 1.8(3) . . . . ?
C1 C2 C7 C6 -177.11(19) . . . . ?
C3 C2 C7 C8 -179.02(17) . . . . ?
C1 C2 C7 C8 2.1(3) . . . . ?
C6 C7 C8 C9 -122.7(2) . . . . ?
C2 C7 C8 C9 58.1(3) . . . . ?
C6 C7 C8 C14 62.0(2) . . . . ?
C2 C7 C8 C14 -117.15(19) . . . . ?
C7 C8 C9 C10 21.9(3) . . . . ?
C14 C8 C9 C10 -162.3(2) . . . . ?
C7 C8 C9 C12 -170.56(16) . . . . ?
C14 C8 C9 C12 5.2(2) . . . . ?
C11 O1 C10 C9 3.6(2) . . . . ?
C8 C9 C10 O1 144.0(2) . . . . ?
C12 C9 C10 O1 -24.1(2) . . . . ?
C10 O1 C11 C12 17.7(2) . . . . ?
C8 C9 C12 C11 -137.38(18) . . . . ?
C10 C9 C12 C11 33.62(19) . . . . ?
C8 C9 C12 C21 105.6(2) . . . . ?
C10 C9 C12 C21 -83.4(2) . . . . ?
C8 C9 C12 C13 -15.3(2) . . . . ?
C10 C9 C12 C13 155.70(16) . . . . ?
O1 C11 C12 C9 -30.8(2) . . . . ?
O1 C11 C12 C21 86.3(2) . . . . ?
O1 C11 C12 C13 -140.70(18) . . . . ?
C9 C12 C13 C14 18.63(19) . . . . ?
C11 C12 C13 C14 127.26(18) . . . . ?
C21 C12 C13 C14 -100.74(19) . . . . ?
C9 C8 C14 C22 -114.57(18) . . . . ?
C7 C8 C14 C22 61.4(2) . . . . ?
C9 C8 C14 C15 123.58(16) . . . . ?
C7 C8 C14 C15 -60.5(2) . . . . ?
C9 C8 C14 C13 7.03(19) . . . . ?
C7 C8 C14 C13 -177.03(15) . . . . ?
C12 C13 C14 C22 101.56(19) . . . . ?
C12 C13 C14 C15 -132.96(16) . . . . ?
C12 C13 C14 C8 -16.04(19) . . . . ?
C22 C14 C15 C20 6.9(2) . . . . ?
C8 C14 C15 C20 127.48(18) . . . . ?
C13 C14 C15 C20 -120.66(19) . . . . ?
C22 C14 C15 C16 -173.63(16) . . . . ?
C8 C14 C15 C16 -53.0(2) . . . . ?
C13 C14 C15 C16 58.8(2) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 179.55(16) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C16 C15 C20 C19 1.0(3) . . . . ?
C14 C15 C20 C19 -179.47(17) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C15 C14 C22 C23 -108.8(3) . . . . ?
C8 C14 C22 C23 129.8(2) . . . . ?
C13 C14 C22 C23 16.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
