# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_mo_100738lt_0m
_database_code_depnum_ccdc_archive 'CCDC 873228'
#TrackingRef 'mo_100738lt_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 O'
_chemical_formula_weight         274.34

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   'P 1 21/n 1'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   11.9938(7)
_cell_length_b                   7.7257(4)
_cell_length_c                   16.3449(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.2810(10)
_cell_angle_gamma                90.00
_cell_volume                     1460.98(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3542
_cell_measurement_theta_min      2.5836
_cell_measurement_theta_max      26.3697

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_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       '\f and \w scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10413
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.42
_reflns_number_total             2835
_reflns_number_gt                2192
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0742P)^2^+0.6675P] where P=(Fo^2^+2Fc^2^)/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         2835
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.38980(14) 0.1955(2) 0.20979(10) 0.0240(4) Uani 1 1 d . . .
C2 C 0.47110(14) 0.1067(2) 0.27147(10) 0.0256(4) Uani 1 1 d . . .
H2 H 0.5251 0.0358 0.2564 0.031 Uiso 1 1 calc R . .
C3 C 0.47119(14) 0.1245(2) 0.35618(10) 0.0251(4) Uani 1 1 d . . .
H3 H 0.5264 0.0657 0.3974 0.030 Uiso 1 1 calc R . .
C4 C 0.39092(13) 0.2279(2) 0.38088(10) 0.0222(4) Uani 1 1 d . . .
C5 C 0.30863(13) 0.3140(2) 0.31697(10) 0.0236(4) Uani 1 1 d . . .
H5 H 0.2532 0.3827 0.3316 0.028 Uiso 1 1 calc R . .
C6 C 0.30809(13) 0.2991(2) 0.23247(10) 0.0247(4) Uani 1 1 d . . .
H6 H 0.2532 0.3581 0.1910 0.030 Uiso 1 1 calc R . .
C7 C 0.39061(14) 0.2470(2) 0.47156(10) 0.0222(4) Uani 1 1 d . . .
C8 C 0.49157(13) 0.2844(2) 0.53619(10) 0.0222(4) Uani 1 1 d . . .
C9 C 0.48303(13) 0.3054(2) 0.61902(10) 0.0226(4) Uani 1 1 d . . .
H9 H 0.5496 0.3319 0.6612 0.027 Uiso 1 1 calc R . .
C10 C 0.37905(14) 0.2884(2) 0.64144(10) 0.0234(4) Uani 1 1 d . . .
C11 C 0.27996(14) 0.2511(2) 0.57628(11) 0.0273(4) Uani 1 1 d . . .
H11 H 0.2091 0.2394 0.5889 0.033 Uiso 1 1 calc R . .
C12 C 0.28594(14) 0.2314(2) 0.49358(10) 0.0255(4) Uani 1 1 d . . .
H12 H 0.2188 0.2072 0.4515 0.031 Uiso 1 1 calc R . .
C13 C 0.37396(14) 0.3062(2) 0.73129(10) 0.0249(4) Uani 1 1 d . . .
C14 C 0.45227(15) 0.4117(2) 0.78847(11) 0.0297(4) Uani 1 1 d . . .
H14 H 0.5088 0.4716 0.7705 0.036 Uiso 1 1 calc R . .
C15 C 0.44640(16) 0.4278(2) 0.87223(11) 0.0339(4) Uani 1 1 d . . .
H15 H 0.4991 0.4980 0.9097 0.041 Uiso 1 1 calc R . .
C16 C 0.36297(16) 0.3403(3) 0.89983(11) 0.0345(4) Uani 1 1 d . . .
H16 H 0.3585 0.3530 0.9555 0.041 Uiso 1 1 calc R . .
C17 C 0.28570(16) 0.2331(3) 0.84424(11) 0.0340(4) Uani 1 1 d . . .
H17 H 0.2300 0.1724 0.8628 0.041 Uiso 1 1 calc R . .
C18 C 0.29164(15) 0.2163(2) 0.76078(11) 0.0283(4) Uani 1 1 d . . .
H18 H 0.2398 0.1438 0.7240 0.034 Uiso 1 1 calc R . .
C19 C 0.46212(17) 0.0741(3) 0.09981(11) 0.0384(5) Uani 1 1 d . . .
H19A H 0.5400 0.1125 0.1239 0.058 Uiso 1 1 calc R . .
H19B H 0.4462 0.0731 0.0391 0.058 Uiso 1 1 calc R . .
H19C H 0.4529 -0.0405 0.1197 0.058 Uiso 1 1 calc R . .
C20 C 0.60893(14) 0.3004(2) 0.51961(11) 0.0296(4) Uani 1 1 d . . .
H20A H 0.6579 0.3707 0.5629 0.044 Uiso 1 1 calc R . .
H20B H 0.6011 0.3531 0.4652 0.044 Uiso 1 1 calc R . .
H20C H 0.6425 0.1874 0.5202 0.044 Uiso 1 1 calc R . .
O1 O 0.38400(10) 0.18858(17) 0.12463(7) 0.0304(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
C1 0.0255(8) 0.0204(9) 0.0267(8) -0.0014(6) 0.0077(6) -0.0042(7)
C2 0.0266(8) 0.0169(9) 0.0350(9) -0.0001(6) 0.0109(7) 0.0027(7)
C3 0.0264(8) 0.0178(9) 0.0297(8) 0.0031(6) 0.0051(6) 0.0023(7)
C4 0.0225(8) 0.0144(8) 0.0297(8) 0.0006(6) 0.0068(6) -0.0019(6)
C5 0.0212(7) 0.0199(9) 0.0296(8) -0.0016(6) 0.0065(6) 0.0005(7)
C6 0.0230(8) 0.0203(9) 0.0289(8) 0.0006(6) 0.0035(6) 0.0006(7)
C7 0.0238(8) 0.0143(9) 0.0279(8) 0.0025(6) 0.0057(6) 0.0015(6)
C8 0.0233(8) 0.0145(8) 0.0286(8) 0.0047(6) 0.0067(6) 0.0032(6)
C9 0.0234(8) 0.0165(9) 0.0270(8) 0.0036(6) 0.0049(6) 0.0011(6)
C10 0.0269(8) 0.0146(8) 0.0301(8) 0.0020(6) 0.0099(6) 0.0022(7)
C11 0.0244(8) 0.0230(10) 0.0370(9) -0.0009(7) 0.0127(7) -0.0009(7)
C12 0.0214(8) 0.0219(9) 0.0321(9) -0.0022(6) 0.0048(6) -0.0016(7)
C13 0.0276(8) 0.0176(9) 0.0313(8) 0.0018(6) 0.0107(6) 0.0047(7)
C14 0.0331(9) 0.0219(9) 0.0363(9) -0.0004(7) 0.0130(7) 0.0008(8)
C15 0.0404(10) 0.0275(10) 0.0333(9) -0.0050(7) 0.0089(7) 0.0024(8)
C16 0.0438(10) 0.0319(11) 0.0298(9) -0.0013(7) 0.0136(8) 0.0067(9)
C17 0.0371(10) 0.0312(11) 0.0380(10) 0.0029(7) 0.0177(8) 0.0020(8)
C18 0.0302(9) 0.0239(10) 0.0336(9) -0.0003(7) 0.0132(7) 0.0010(7)
C19 0.0448(11) 0.0403(12) 0.0345(9) -0.0011(8) 0.0185(8) 0.0098(9)
C20 0.0290(9) 0.0285(10) 0.0307(9) 0.0005(7) 0.0070(7) 0.0008(8)
O1 0.0327(7) 0.0333(8) 0.0264(6) -0.0015(5) 0.0099(5) 0.0056(6)

_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 O1 1.3762(19) . ?
C1 C2 1.386(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(2) . ?
C4 C7 1.490(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.399(2) . ?
C7 C8 1.411(2) . ?
C8 C9 1.394(2) . ?
C8 C20 1.507(2) . ?
C9 C10 1.396(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.401(2) . ?
C10 C13 1.492(2) . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.393(2) . ?
C13 C14 1.399(2) . ?
C14 C15 1.395(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.423(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O1 C1 C2 123.70(14) . . ?
O1 C1 C6 116.18(14) . . ?
C2 C1 C6 120.12(14) . . ?
C1 C2 C3 119.40(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.80(14) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 117.50(15) . . ?
C3 C4 C7 121.94(14) . . ?
C5 C4 C7 120.56(14) . . ?
C6 C5 C4 121.41(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.75(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C12 C7 C8 118.42(15) . . ?
C12 C7 C4 119.00(14) . . ?
C8 C7 C4 122.56(14) . . ?
C9 C8 C7 118.87(14) . . ?
C9 C8 C20 118.45(14) . . ?
C7 C8 C20 122.68(14) . . ?
C8 C9 C10 122.93(14) . . ?
C8 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C9 C10 C11 117.22(15) . . ?
C9 C10 C13 121.40(14) . . ?
C11 C10 C13 121.37(15) . . ?
C12 C11 C10 120.95(15) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 121.60(15) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C18 C13 C14 118.14(15) . . ?
C18 C13 C10 120.74(15) . . ?
C14 C13 C10 121.12(15) . . ?
C15 C14 C13 120.60(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.41(17) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.70(16) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.98(17) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 121.14(16) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 O1 C19 116.81(13) . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.045