# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_4
_database_code_depnum_ccdc_archive 'CCDC 921792'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O'
_chemical_formula_sum            'C22 H20 O'
_chemical_formula_weight         300.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   16.0527(3)
_cell_length_b                   5.53030(10)
_cell_length_c                   20.7663(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.425(2)
_cell_angle_gamma                90.00
_cell_volume                     1665.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4160
_cell_measurement_theta_min      2.9430
_cell_measurement_theta_max      73.1174
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4297
_exptl_crystal_size_mid          0.1639
_exptl_crystal_size_min          0.0755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_number            6464
_diffrn_reflns_av_R_equivalents  0.0109
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         73.27
_reflns_number_total             3240
_reflns_number_gt                2902
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_Acta
_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^)+(0.0523P)^2^+0.3402P] 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         3240
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O23 O 0.43799(6) 1.29652(17) 0.54377(5) 0.0452(2) Uani 1 1 d . . .
C1 C 0.29253(8) 0.7445(2) 0.68511(6) 0.0378(3) Uani 1 1 d . . .
H1 H 0.3366 0.6294 0.7141 0.045 Uiso 1 1 calc R . .
C2 C 0.20025(9) 0.7145(2) 0.67032(7) 0.0438(3) Uani 1 1 d . . .
H2 H 0.1816 0.5792 0.6892 0.053 Uiso 1 1 calc R . .
C3 C 0.13529(8) 0.8806(3) 0.62833(7) 0.0449(3) Uani 1 1 d . . .
H3 H 0.0721 0.8599 0.6183 0.054 Uiso 1 1 calc R . .
C4 C 0.16283(8) 1.0770(2) 0.60110(7) 0.0448(3) Uani 1 1 d . . .
H4 H 0.1186 1.1919 0.5722 0.054 Uiso 1 1 calc R . .
C5 C 0.25524(8) 1.1065(2) 0.61593(6) 0.0380(3) Uani 1 1 d . . .
H5 H 0.2736 1.2420 0.5970 0.046 Uiso 1 1 calc R . .
C6 C 0.32111(7) 0.9410(2) 0.65800(6) 0.0318(2) Uani 1 1 d . . .
C7 C 0.42054(7) 0.9706(2) 0.67096(6) 0.0357(3) Uani 1 1 d . . .
H7A H 0.4612 0.9067 0.7188 0.043 Uiso 1 1 calc R . .
H7B H 0.4344 1.1446 0.6700 0.043 Uiso 1 1 calc R . .
C8 C 0.44047(7) 0.8368(2) 0.61440(6) 0.0348(3) Uani 1 1 d . . .
H8A H 0.4253 0.6634 0.6148 0.042 Uiso 1 1 calc R . .
H8B H 0.4003 0.9024 0.5667 0.042 Uiso 1 1 calc R . .
C9 C 0.54007(7) 0.8606(2) 0.62699(5) 0.0300(2) Uani 1 1 d . . .
C10 C 0.57382(7) 1.04955(19) 0.59962(5) 0.0296(2) Uani 1 1 d . . .
C11 C 0.66691(7) 1.05448(19) 0.61238(6) 0.0305(2) Uani 1 1 d . . .
H11 H 0.6883 1.1817 0.5926 0.037 Uiso 1 1 calc R . .
C12 C 0.72869(7) 0.8790(2) 0.65310(6) 0.0311(2) Uani 1 1 d . . .
C13 C 0.69543(8) 0.6958(2) 0.68149(6) 0.0350(2) Uani 1 1 d . . .
H13 H 0.7365 0.5748 0.7104 0.042 Uiso 1 1 calc R . .
C14 C 0.60335(8) 0.6871(2) 0.66832(6) 0.0340(2) Uani 1 1 d . . .
H14 H 0.5826 0.5585 0.6881 0.041 Uiso 1 1 calc R . .
C15 C 0.82883(7) 0.8834(2) 0.66571(6) 0.0384(3) Uani 1 1 d . . .
H15A H 0.8682 0.8765 0.7177 0.046 Uiso 1 1 calc R . .
H15B H 0.8414 1.0389 0.6480 0.046 Uiso 1 1 calc R . .
C16 C 0.85594(7) 0.6781(2) 0.63002(6) 0.0322(2) Uani 1 1 d . . .
C17 C 0.79743(8) 0.5970(2) 0.56211(6) 0.0408(3) Uani 1 1 d . . .
H17 H 0.7379 0.6668 0.5380 0.049 Uiso 1 1 calc R . .
C18 C 0.82474(9) 0.4161(3) 0.52920(6) 0.0462(3) Uani 1 1 d . . .
H18 H 0.7840 0.3632 0.4827 0.055 Uiso 1 1 calc R . .
C19 C 0.91100(9) 0.3122(3) 0.56374(7) 0.0459(3) Uani 1 1 d . . .
H19 H 0.9301 0.1897 0.5409 0.055 Uiso 1 1 calc R . .
C20 C 0.96920(8) 0.3877(3) 0.63163(7) 0.0466(3) Uani 1 1 d . . .
H20 H 1.0282 0.3152 0.6560 0.056 Uiso 1 1 calc R . .
C21 C 0.94174(7) 0.5692(2) 0.66431(6) 0.0403(3) Uani 1 1 d . . .
H21 H 0.9824 0.6200 0.7110 0.048 Uiso 1 1 calc R . .
C22 C 0.51701(8) 1.2498(2) 0.55548(6) 0.0363(3) Uani 1 1 d . . .
H22 H 0.5453 1.3528 0.5340 0.044 Uiso 1 1 calc R . .
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
O23 0.0343(4) 0.0478(5) 0.0462(5) -0.0022(4) 0.0102(4) 0.0128(4)
C1 0.0388(6) 0.0373(6) 0.0382(6) -0.0005(5) 0.0173(5) 0.0028(5)
C2 0.0461(7) 0.0437(7) 0.0491(7) -0.0028(5) 0.0274(6) -0.0080(5)
C3 0.0313(6) 0.0544(8) 0.0548(7) -0.0094(6) 0.0238(5) -0.0029(5)
C4 0.0351(6) 0.0456(7) 0.0540(7) 0.0006(6) 0.0194(5) 0.0103(5)
C5 0.0377(6) 0.0362(6) 0.0452(6) 0.0013(5) 0.0226(5) 0.0031(5)
C6 0.0314(5) 0.0357(6) 0.0323(5) -0.0075(4) 0.0175(4) 0.0013(4)
C7 0.0300(5) 0.0436(6) 0.0354(5) -0.0078(5) 0.0160(4) -0.0003(5)
C8 0.0294(5) 0.0386(6) 0.0401(6) -0.0094(5) 0.0186(4) -0.0023(4)
C9 0.0279(5) 0.0344(5) 0.0304(5) -0.0074(4) 0.0149(4) 0.0001(4)
C10 0.0289(5) 0.0312(5) 0.0285(5) -0.0038(4) 0.0120(4) 0.0030(4)
C11 0.0316(5) 0.0296(5) 0.0330(5) -0.0022(4) 0.0164(4) -0.0008(4)
C12 0.0261(5) 0.0351(6) 0.0322(5) -0.0046(4) 0.0125(4) 0.0002(4)
C13 0.0331(5) 0.0360(6) 0.0347(5) 0.0046(4) 0.0135(4) 0.0068(4)
C14 0.0360(6) 0.0354(6) 0.0351(5) 0.0016(4) 0.0193(5) -0.0007(4)
C15 0.0257(5) 0.0432(6) 0.0442(6) -0.0054(5) 0.0131(5) -0.0009(5)
C16 0.0239(5) 0.0388(6) 0.0358(5) 0.0024(4) 0.0145(4) -0.0004(4)
C17 0.0297(5) 0.0531(7) 0.0351(6) 0.0031(5) 0.0097(5) 0.0086(5)
C18 0.0415(7) 0.0606(8) 0.0327(6) -0.0046(6) 0.0123(5) 0.0043(6)
C19 0.0402(6) 0.0545(8) 0.0472(7) -0.0067(6) 0.0229(5) 0.0052(6)
C20 0.0268(5) 0.0568(8) 0.0523(7) -0.0041(6) 0.0133(5) 0.0083(5)
C21 0.0243(5) 0.0518(7) 0.0403(6) -0.0050(5) 0.0095(4) 0.0013(5)
C22 0.0372(6) 0.0353(6) 0.0340(5) -0.0019(5) 0.0131(5) 0.0055(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
O23 C22 1.2125(14) . ?
C1 C2 1.3877(16) . ?
C1 C6 1.3891(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3822(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3818(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3892(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3879(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5092(14) . ?
C7 C8 1.5337(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5111(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3932(16) . ?
C9 C10 1.4046(15) . ?
C10 C11 1.4014(14) . ?
C10 C22 1.4768(15) . ?
C11 C12 1.3859(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3890(16) . ?
C12 C15 1.5139(14) . ?
C13 C14 1.3836(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5180(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.3874(15) . ?
C16 C17 1.3908(16) . ?
C17 C18 1.3849(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3816(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3798(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3852(18) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
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
C2 C1 C6 120.71(11) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.32(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.55(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.03(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.97(11) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 118.43(10) . . ?
C5 C6 C7 120.15(10) . . ?
C1 C6 C7 121.37(10) . . ?
C6 C7 C8 111.31(9) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 112.24(9) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 117.11(9) . . ?
C14 C9 C8 118.95(10) . . ?
C10 C9 C8 123.94(10) . . ?
C11 C10 C9 120.21(10) . . ?
C11 C10 C22 115.28(10) . . ?
C9 C10 C22 124.50(10) . . ?
C12 C11 C10 121.83(10) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 117.71(10) . . ?
C11 C12 C15 121.52(10) . . ?
C13 C12 C15 120.77(10) . . ?
C14 C13 C12 120.94(10) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 122.16(10) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C12 C15 C16 114.15(9) . . ?
C12 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C12 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C21 C16 C17 118.03(11) . . ?
C21 C16 C15 120.24(10) . . ?
C17 C16 C15 121.71(10) . . ?
C18 C17 C16 120.95(10) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.21(11) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.52(12) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.10(11) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 121.17(11) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
O23 C22 C10 126.75(11) . . ?
O23 C22 H22 116.6 . . ?
C10 C22 H22 116.6 . . ?
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        66.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031


data_anti9
_database_code_depnum_ccdc_archive 'CCDC 921793'
#TrackingRef 'web_deposit_cif_file_0_LaureGuenee_1359132082.compounds_all.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 O2'
_chemical_formula_sum            'C20 H24 O2'
_chemical_formula_weight         296.39
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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
_cell_length_a                   9.79459(15)
_cell_length_b                   10.18235(18)
_cell_length_c                   34.1007(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3400.93(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5953
_cell_measurement_theta_min      2.5893
_cell_measurement_theta_max      73.2040
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3199
_exptl_crystal_size_mid          0.2088
_exptl_crystal_size_min          0.1123
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_reflns_number            10550
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         73.36
_reflns_number_total             3356
_reflns_number_gt                3100
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  ShelX_Acta
_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^)+(0.0647P)^2^+1.4614P] 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         3356
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O2 O 0.62974(12) 0.39868(11) 0.47130(3) 0.0435(3) Uani 1 1 d . . .
O21 O 0.5148(3) 0.4903(2) 0.28558(8) 0.1341(9) Uani 1 1 d . . .
C1 C 0.76759(19) 0.42550(19) 0.48182(5) 0.0535(4) Uani 1 1 d . . .
H1A H 0.7696 0.4923 0.5025 0.080 Uiso 1 1 calc R . .
H1B H 0.8172 0.4578 0.4588 0.080 Uiso 1 1 calc R . .
H1C H 0.8109 0.3448 0.4914 0.080 Uiso 1 1 calc R . .
C3 C 0.60858(15) 0.31263(13) 0.44115(4) 0.0324(3) Uani 1 1 d . . .
C4 C 0.71040(15) 0.24348(15) 0.42209(4) 0.0388(3) Uani 1 1 d . . .
H4 H 0.8030 0.2533 0.4299 0.047 Uiso 1 1 calc R . .
C5 C 0.67636(14) 0.15924(14) 0.39139(4) 0.0356(3) Uani 1 1 d . . .
H5 H 0.7471 0.1110 0.3789 0.043 Uiso 1 1 calc R . .
C6 C 0.54360(13) 0.14318(12) 0.37838(4) 0.0278(3) Uani 1 1 d . . .
C7 C 0.44253(13) 0.21395(13) 0.39842(4) 0.0316(3) Uani 1 1 d . . .
H7 H 0.3500 0.2053 0.3905 0.038 Uiso 1 1 calc R . .
C8 C 0.47389(15) 0.29593(13) 0.42946(4) 0.0337(3) Uani 1 1 d . . .
H8 H 0.4029 0.3410 0.4429 0.040 Uiso 1 1 calc R . .
C9 C 0.50782(13) 0.06216(13) 0.34193(4) 0.0307(3) Uani 1 1 d . . .
C10 C 0.38307(14) -0.02960(14) 0.34926(4) 0.0344(3) Uani 1 1 d . . .
H10A H 0.3052 0.0252 0.3579 0.041 Uiso 1 1 calc R . .
H10B H 0.3572 -0.0705 0.3240 0.041 Uiso 1 1 calc R . .
C11 C 0.40358(13) -0.13751(13) 0.37900(4) 0.0327(3) Uani 1 1 d . . .
C12 C 0.38783(15) -0.11391(14) 0.41904(4) 0.0358(3) Uani 1 1 d . . .
H12 H 0.3652 -0.0280 0.4278 0.043 Uiso 1 1 calc R . .
C13 C 0.40453(15) -0.21334(15) 0.44625(4) 0.0391(3) Uani 1 1 d . . .
H13 H 0.3938 -0.1950 0.4734 0.047 Uiso 1 1 calc R . .
C14 C 0.43690(15) -0.33979(15) 0.43419(5) 0.0397(3) Uani 1 1 d . . .
H14 H 0.4481 -0.4081 0.4529 0.048 Uiso 1 1 calc R . .
C15 C 0.45261(15) -0.36505(14) 0.39460(5) 0.0395(3) Uani 1 1 d . . .
H15 H 0.4747 -0.4513 0.3861 0.047 Uiso 1 1 calc R . .
C16 C 0.43635(15) -0.26528(14) 0.36731(4) 0.0370(3) Uani 1 1 d . . .
H16 H 0.4477 -0.2841 0.3402 0.044 Uiso 1 1 calc R . .
C17 C 0.46399(16) 0.15774(15) 0.30882(4) 0.0395(3) Uani 1 1 d . . .
H17A H 0.4446 0.1055 0.2850 0.047 Uiso 1 1 calc R . .
H17B H 0.3777 0.2008 0.3168 0.047 Uiso 1 1 calc R . .
C18 C 0.56870(18) 0.26608(16) 0.29805(4) 0.0451(4) Uani 1 1 d . . .
H18 H 0.6461 0.2585 0.3170 0.054 Uiso 1 1 calc R . .
C19 C 0.6289(3) 0.2541(3) 0.25741(6) 0.0837(8) Uani 1 1 d . . .
H19A H 0.5553 0.2554 0.2379 0.125 Uiso 1 1 calc R . .
H19B H 0.6794 0.1713 0.2553 0.125 Uiso 1 1 calc R . .
H19C H 0.6910 0.3278 0.2526 0.125 Uiso 1 1 calc R . .
C20 C 0.5059(3) 0.3977(2) 0.30410(8) 0.0786(7) Uani 1 1 d . . .
H20 H 0.4502 0.4055 0.3268 0.094 Uiso 1 1 calc R . .
C22 C 0.62822(15) -0.02165(15) 0.32784(4) 0.0394(3) Uani 1 1 d . . .
H22A H 0.6581 -0.0797 0.3491 0.059 Uiso 1 1 calc R . .
H22B H 0.7038 0.0358 0.3201 0.059 Uiso 1 1 calc R . .
H22C H 0.5997 -0.0747 0.3053 0.059 Uiso 1 1 calc R . .
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
O2 0.0500(6) 0.0450(6) 0.0356(5) -0.0110(4) -0.0043(4) -0.0019(5)
O21 0.158(2) 0.0754(13) 0.168(2) 0.0419(14) 0.0040(18) 0.0189(14)
C1 0.0574(11) 0.0611(10) 0.0419(8) -0.0109(8) -0.0052(8) -0.0192(9)
C3 0.0399(7) 0.0306(7) 0.0268(6) 0.0003(5) -0.0022(5) -0.0004(5)
C4 0.0298(7) 0.0490(8) 0.0377(7) -0.0054(6) -0.0066(5) 0.0017(6)
C5 0.0283(7) 0.0431(8) 0.0354(7) -0.0056(6) -0.0002(5) 0.0051(6)
C6 0.0284(6) 0.0279(6) 0.0271(6) 0.0023(5) 0.0007(5) 0.0008(5)
C7 0.0258(6) 0.0312(6) 0.0377(7) -0.0009(5) -0.0004(5) 0.0012(5)
C8 0.0339(7) 0.0307(7) 0.0363(7) -0.0026(5) 0.0042(6) 0.0030(5)
C9 0.0298(7) 0.0328(7) 0.0296(6) -0.0018(5) 0.0005(5) -0.0008(5)
C10 0.0307(7) 0.0360(7) 0.0365(7) -0.0047(6) -0.0019(5) -0.0021(5)
C11 0.0257(6) 0.0328(7) 0.0397(7) -0.0039(6) 0.0030(5) -0.0045(5)
C12 0.0358(7) 0.0313(7) 0.0404(7) -0.0048(6) 0.0071(6) -0.0021(6)
C13 0.0388(8) 0.0399(8) 0.0385(7) -0.0011(6) 0.0073(6) -0.0032(6)
C14 0.0351(7) 0.0350(7) 0.0490(8) 0.0054(6) 0.0039(6) -0.0013(6)
C15 0.0335(7) 0.0304(7) 0.0545(9) -0.0049(6) 0.0047(6) -0.0003(6)
C16 0.0336(7) 0.0369(7) 0.0406(7) -0.0086(6) 0.0043(6) -0.0052(6)
C17 0.0449(8) 0.0427(8) 0.0308(7) 0.0009(6) -0.0062(6) -0.0040(6)
C18 0.0562(10) 0.0457(9) 0.0333(7) 0.0064(6) -0.0036(7) -0.0100(7)
C19 0.115(2) 0.0831(15) 0.0531(12) -0.0021(11) 0.0290(12) -0.0319(14)
C20 0.0977(18) 0.0480(11) 0.0901(16) 0.0048(11) 0.0074(14) -0.0157(11)
C22 0.0362(8) 0.0413(8) 0.0407(8) -0.0093(6) 0.0071(6) -0.0006(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
O2 C3 1.3667(16) . ?
O2 C1 1.423(2) . ?
O21 C20 1.139(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.383(2) . ?
C3 C8 1.389(2) . ?
C4 C5 1.394(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3836(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4021(18) . ?
C6 C9 1.5325(17) . ?
C7 C8 1.3826(19) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C22 1.5330(19) . ?
C9 C17 1.5514(19) . ?
C9 C10 1.5582(19) . ?
C10 C11 1.509(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.395(2) . ?
C11 C16 1.3981(19) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.550(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.489(3) . ?
C18 C19 1.511(3) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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 O2 C1 117.16(12) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C3 C4 124.79(13) . . ?
O2 C3 C8 116.01(12) . . ?
C4 C3 C8 119.21(13) . . ?
C3 C4 C5 119.58(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 122.57(13) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C7 116.53(12) . . ?
C5 C6 C9 122.58(12) . . ?
C7 C6 C9 120.69(12) . . ?
C8 C7 C6 121.77(13) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C3 120.31(13) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C22 C9 C6 112.22(11) . . ?
C22 C9 C17 109.50(12) . . ?
C6 C9 C17 108.42(11) . . ?
C22 C9 C10 108.64(11) . . ?
C6 C9 C10 111.85(11) . . ?
C17 C9 C10 106.01(11) . . ?
C11 C10 C9 116.10(11) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C16 117.70(13) . . ?
C12 C11 C10 121.19(12) . . ?
C16 C11 C10 121.10(13) . . ?
C13 C12 C11 121.16(13) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.49(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.14(14) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.41(14) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 121.10(14) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C18 C17 C9 115.84(12) . . ?
C18 C17 H17A 108.3 . . ?
C9 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C9 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C20 C18 C19 111.16(18) . . ?
C20 C18 C17 109.54(16) . . ?
C19 C18 C17 114.70(15) . . ?
C20 C18 H18 107.0 . . ?
C19 C18 H18 107.0 . . ?
C17 C18 H18 107.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 C20 C18 129.6(3) . . ?
O21 C20 H20 115.2 . . ?
C18 C20 H20 115.2 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.036