# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_4a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-hydroxy-2,5,5-trimethyl-3,4-diphenylcyclopentanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.38

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/n'
_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                   6.0600(2)
_cell_length_b                   17.8904(7)
_cell_length_c                   15.1129(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9109(16)
_cell_angle_gamma                90.00
_cell_volume                     1626.57(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      71.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.7730
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10710
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         71.37
_reflns_number_total             3159
_reflns_number_gt                2836
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_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)+(0.0693P)²+0.3401P] 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         3159
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.29138(16) 0.05443(5) 0.54081(6) 0.0364(2) Uani 1 1 d . . .
O2 O 0.50131(13) 0.06783(5) 0.36631(6) 0.0286(2) Uani 1 1 d . . .
H2O H 0.577(3) 0.0309(11) 0.3980(12) 0.050(5) Uiso 1 1 d . . .
C1 C 0.26021(18) 0.09168(7) 0.47307(8) 0.0260(3) Uani 1 1 d . . .
C2 C 0.27037(18) 0.06170(6) 0.37868(8) 0.0244(3) Uani 1 1 d . . .
C3 C 0.14141(17) 0.12223(6) 0.32149(8) 0.0224(2) Uani 1 1 d . . .
H3 H -0.0194 0.1152 0.3282 0.027 Uiso 1 1 calc R . .
C4 C 0.21582(17) 0.19537(6) 0.37081(7) 0.0218(2) Uani 1 1 d . . .
H4 H 0.3749 0.2040 0.3622 0.026 Uiso 1 1 calc R . .
C5 C 0.20944(18) 0.17503(6) 0.47111(8) 0.0240(3) Uani 1 1 d . . .
C6 C 0.1839(2) -0.01711(7) 0.36335(9) 0.0331(3) Uani 1 1 d . . .
H6A H 0.1950 -0.0318 0.3016 0.040 Uiso 1 1 calc R . .
H6B H 0.0282 -0.0193 0.3747 0.040 Uiso 1 1 calc R . .
H6C H 0.2726 -0.0514 0.4039 0.040 Uiso 1 1 calc R . .
C7 C 0.16180(18) 0.11694(6) 0.22315(8) 0.0233(2) Uani 1 1 d . . .
C8 C 0.3554(2) 0.13654(7) 0.18756(9) 0.0308(3) Uani 1 1 d . . .
H8 H 0.4770 0.1570 0.2254 0.037 Uiso 1 1 calc R . .
C9 C 0.3729(2) 0.12652(8) 0.09765(9) 0.0363(3) Uani 1 1 d . . .
H9 H 0.5066 0.1397 0.0745 0.044 Uiso 1 1 calc R . .
C10 C 0.1967(2) 0.09740(8) 0.04143(9) 0.0380(3) Uani 1 1 d . . .
H10 H 0.2091 0.0905 -0.0201 0.046 Uiso 1 1 calc R . .
C11 C 0.0029(2) 0.07840(8) 0.07549(9) 0.0365(3) Uani 1 1 d . . .
H11 H -0.1192 0.0587 0.0372 0.044 Uiso 1 1 calc R . .
C12 C -0.0141(2) 0.08802(7) 0.16562(8) 0.0281(3) Uani 1 1 d . . .
H12 H -0.1481 0.0746 0.1884 0.034 Uiso 1 1 calc R . .
C13 C 0.08845(19) 0.26566(6) 0.34128(8) 0.0247(3) Uani 1 1 d . . .
C14 C 0.1885(2) 0.33512(7) 0.35882(9) 0.0332(3) Uani 1 1 d . . .
H14 H 0.3376 0.3375 0.3865 0.040 Uiso 1 1 calc R . .
C15 C 0.0736(3) 0.40100(8) 0.33638(10) 0.0448(4) Uani 1 1 d . . .
H15 H 0.1436 0.4479 0.3496 0.054 Uiso 1 1 calc R . .
C16 C -0.1419(3) 0.39840(9) 0.29489(10) 0.0478(4) Uani 1 1 d . . .
H16 H -0.2200 0.4434 0.2790 0.057 Uiso 1 1 calc R . .
C17 C -0.2437(2) 0.33021(9) 0.27655(10) 0.0440(4) Uani 1 1 d . . .
H17 H -0.3919 0.3283 0.2479 0.053 Uiso 1 1 calc R . .
C18 C -0.1294(2) 0.26429(8) 0.30003(9) 0.0337(3) Uani 1 1 d . . .
H18 H -0.2014 0.2176 0.2877 0.040 Uiso 1 1 calc R . .
C19 C 0.3771(2) 0.21771(8) 0.53563(8) 0.0331(3) Uani 1 1 d . . .
H19A H 0.3411 0.2711 0.5329 0.040 Uiso 1 1 calc R . .
H19B H 0.5269 0.2101 0.5190 0.040 Uiso 1 1 calc R . .
H19C H 0.3710 0.1993 0.5964 0.040 Uiso 1 1 calc R . .
C20 C -0.02512(19) 0.18321(7) 0.49966(9) 0.0288(3) Uani 1 1 d . . .
H20A H -0.1319 0.1554 0.4582 0.035 Uiso 1 1 calc R . .
H20B H -0.0668 0.2362 0.4989 0.035 Uiso 1 1 calc R . .
H20C H -0.0258 0.1632 0.5600 0.035 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 C1 1.2171(15) . ?
O2 C2 1.4382(13) . ?
C1 C5 1.5222(16) . ?
C1 C2 1.5323(16) . ?
C2 C6 1.5122(16) . ?
C2 C3 1.5388(15) . ?
C3 C7 1.5089(16) . ?
C3 C4 1.5460(15) . ?
C4 C13 1.5144(15) . ?
C4 C5 1.5639(15) . ?
C5 C19 1.5257(16) . ?
C5 C20 1.5413(15) . ?
C7 C12 1.3916(16) . ?
C7 C8 1.3930(16) . ?
C8 C9 1.3873(19) . ?
C9 C10 1.384(2) . ?
C10 C11 1.381(2) . ?
C11 C12 1.3889(18) . ?
C13 C18 1.3909(17) . ?
C13 C14 1.3942(17) . ?
C14 C15 1.3900(19) . ?
C15 C16 1.380(2) . ?
C16 C17 1.380(2) . ?
C17 C18 1.3917(19) . ?

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 C5 124.29(11) . . ?
O1 C1 C2 124.88(11) . . ?
C5 C1 C2 110.82(9) . . ?
O2 C2 C6 112.07(9) . . ?
O2 C2 C1 104.06(9) . . ?
C6 C2 C1 114.65(10) . . ?
O2 C2 C3 108.04(9) . . ?
C6 C2 C3 115.27(10) . . ?
C1 C2 C3 101.66(9) . . ?
C7 C3 C2 114.38(9) . . ?
C7 C3 C4 118.31(9) . . ?
C2 C3 C4 103.05(9) . . ?
C13 C4 C3 116.87(9) . . ?
C13 C4 C5 114.05(9) . . ?
C3 C4 C5 103.34(9) . . ?
C1 C5 C19 111.12(10) . . ?
C1 C5 C20 106.18(9) . . ?
C19 C5 C20 109.83(10) . . ?
C1 C5 C4 102.61(9) . . ?
C19 C5 C4 114.26(9) . . ?
C20 C5 C4 112.36(9) . . ?
C12 C7 C8 118.00(11) . . ?
C12 C7 C3 119.43(10) . . ?
C8 C7 C3 122.49(10) . . ?
C9 C8 C7 120.86(12) . . ?
C10 C9 C8 120.39(12) . . ?
C11 C10 C9 119.47(12) . . ?
C10 C11 C12 120.11(12) . . ?
C11 C12 C7 121.16(12) . . ?
C18 C13 C14 117.95(11) . . ?
C18 C13 C4 122.70(11) . . ?
C14 C13 C4 119.31(11) . . ?
C15 C14 C13 121.04(13) . . ?
C16 C15 C14 120.09(14) . . ?
C17 C16 C15 119.77(13) . . ?
C16 C17 C18 120.10(14) . . ?
C13 C18 C17 121.04(13) . . ?

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
O1 C1 C2 O2 -86.91(13) . . . . ?
C5 C1 C2 O2 92.15(10) . . . . ?
O1 C1 C2 C6 35.85(16) . . . . ?
C5 C1 C2 C6 -145.09(10) . . . . ?
O1 C1 C2 C3 160.89(11) . . . . ?
C5 C1 C2 C3 -20.05(11) . . . . ?
O2 C2 C3 C7 58.90(12) . . . . ?
C6 C2 C3 C7 -67.31(12) . . . . ?
C1 C2 C3 C7 168.06(9) . . . . ?
O2 C2 C3 C4 -70.86(11) . . . . ?
C6 C2 C3 C4 162.93(9) . . . . ?
C1 C2 C3 C4 38.30(10) . . . . ?
C7 C3 C4 C13 63.27(13) . . . . ?
C2 C3 C4 C13 -169.42(9) . . . . ?
C7 C3 C4 C5 -170.59(9) . . . . ?
C2 C3 C4 C5 -43.28(10) . . . . ?
O1 C1 C5 C19 50.48(15) . . . . ?
C2 C1 C5 C19 -128.59(10) . . . . ?
O1 C1 C5 C20 -68.91(14) . . . . ?
C2 C1 C5 C20 112.02(10) . . . . ?
O1 C1 C5 C4 173.00(11) . . . . ?
C2 C1 C5 C4 -6.07(11) . . . . ?
C13 C4 C5 C1 157.77(9) . . . . ?
C3 C4 C5 C1 29.86(10) . . . . ?
C13 C4 C5 C19 -81.85(12) . . . . ?
C3 C4 C5 C19 150.24(9) . . . . ?
C13 C4 C5 C20 44.15(13) . . . . ?
C3 C4 C5 C20 -83.76(11) . . . . ?
C2 C3 C7 C12 103.53(12) . . . . ?
C4 C3 C7 C12 -134.76(11) . . . . ?
C2 C3 C7 C8 -73.20(14) . . . . ?
C4 C3 C7 C8 48.52(15) . . . . ?
C12 C7 C8 C9 -0.85(18) . . . . ?
C3 C7 C8 C9 175.92(11) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C7 0.2(2) . . . . ?
C8 C7 C12 C11 0.46(18) . . . . ?
C3 C7 C12 C11 -176.41(11) . . . . ?
C3 C4 C13 C18 24.84(16) . . . . ?
C5 C4 C13 C18 -95.78(13) . . . . ?
C3 C4 C13 C14 -157.72(11) . . . . ?
C5 C4 C13 C14 81.66(13) . . . . ?
C18 C13 C14 C15 0.47(19) . . . . ?
C4 C13 C14 C15 -177.09(12) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C14 C13 C18 C17 0.33(19) . . . . ?
C4 C13 C18 C17 177.80(12) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.91(2) 1.91(2) 2.8122(12) 173.4(17) 3_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        71.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048

_database_code_depnum_ccdc_archive 'CCDC 993484'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_4e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-hydroxy-2,5,5-trimethyl-3,4-diisopropylcyclopentanone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 O2'
_chemical_formula_sum            'C14 H26 O2'
_chemical_formula_weight         226.35

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                   6.191(2)
_cell_length_b                   8.211(3)
_cell_length_c                   14.477(5)
_cell_angle_alpha                93.911(4)
_cell_angle_beta                 96.054(5)
_cell_angle_gamma                109.796(4)
_cell_volume                     684.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2370
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.44

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             252
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9006
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5470
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         26.50
_reflns_number_total             2819
_reflns_number_gt                2247
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_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)+(0.0578P)²+0.2189P] 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         2819
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.4279(2) 0.18993(15) 0.48110(8) 0.0414(3) Uani 1 1 d . . .
O2 O 0.4509(2) -0.07937(16) 0.34510(8) 0.0360(3) Uani 1 1 d . . .
H2O H 0.482(4) -0.098(3) 0.4013(17) 0.065(7) Uiso 1 1 d . . .
C1 C 0.3492(3) 0.15841(19) 0.39914(10) 0.0257(3) Uani 1 1 d . . .
C2 C 0.2546(3) -0.02607(19) 0.34672(10) 0.0245(3) Uani 1 1 d . . .
C3 C 0.1692(2) 0.00263(18) 0.24673(10) 0.0226(3) Uani 1 1 d . . .
H3 H 0.0067 -0.0002 0.2478 0.027 Uiso 1 1 calc R . .
C4 C 0.3156(2) 0.19442(18) 0.23714(9) 0.0211(3) Uani 1 1 d . . .
H4 H 0.4746 0.1957 0.2291 0.025 Uiso 1 1 calc R . .
C5 C 0.3372(3) 0.29301(18) 0.33476(10) 0.0237(3) Uani 1 1 d . . .
C6 C 0.0725(3) -0.1470(2) 0.39735(12) 0.0430(5) Uani 1 1 d . . .
H6A H 0.1439 -0.1566 0.4595 0.052 Uiso 1 1 calc R . .
H6B H 0.0080 -0.2625 0.3615 0.052 Uiso 1 1 calc R . .
H6C H -0.0517 -0.0999 0.4037 0.052 Uiso 1 1 calc R . .
C7 C 0.1576(3) -0.13140(19) 0.16427(10) 0.0271(3) Uani 1 1 d . . .
H7 H 0.0952 -0.0908 0.1072 0.033 Uiso 1 1 calc R . .
C8 C 0.3874(3) -0.1467(3) 0.14397(12) 0.0418(4) Uani 1 1 d . . .
H8A H 0.3590 -0.2353 0.0908 0.050 Uiso 1 1 calc R . .
H8B H 0.4612 -0.1804 0.1991 0.050 Uiso 1 1 calc R . .
H8C H 0.4896 -0.0343 0.1290 0.050 Uiso 1 1 calc R . .
C9 C -0.0161(3) -0.3112(2) 0.17183(12) 0.0396(4) Uani 1 1 d . . .
H9A H -0.0165 -0.3922 0.1188 0.048 Uiso 1 1 calc R . .
H9B H -0.1712 -0.3044 0.1713 0.048 Uiso 1 1 calc R . .
H9C H 0.0277 -0.3529 0.2303 0.048 Uiso 1 1 calc R . .
C10 C 0.2389(3) 0.2823(2) 0.15454(10) 0.0265(3) Uani 1 1 d . . .
H10 H 0.2872 0.4089 0.1772 0.032 Uiso 1 1 calc R . .
C11 C 0.3666(3) 0.2711(2) 0.07066(11) 0.0364(4) Uani 1 1 d . . .
H11A H 0.5337 0.3105 0.0916 0.044 Uiso 1 1 calc R . .
H11B H 0.3347 0.3454 0.0249 0.044 Uiso 1 1 calc R . .
H11C H 0.3132 0.1503 0.0418 0.044 Uiso 1 1 calc R . .
C12 C -0.0218(3) 0.2206(2) 0.12271(11) 0.0329(4) Uani 1 1 d . . .
H12A H -0.0528 0.2825 0.0702 0.040 Uiso 1 1 calc R . .
H12B H -0.1003 0.2447 0.1746 0.040 Uiso 1 1 calc R . .
H12C H -0.0797 0.0952 0.1029 0.040 Uiso 1 1 calc R . .
C13 C 0.5510(3) 0.4585(2) 0.35533(12) 0.0341(4) Uani 1 1 d . . .
H13A H 0.6885 0.4315 0.3430 0.041 Uiso 1 1 calc R . .
H13B H 0.5699 0.5049 0.4210 0.041 Uiso 1 1 calc R . .
H13C H 0.5318 0.5454 0.3152 0.041 Uiso 1 1 calc R . .
C14 C 0.1208(3) 0.3362(2) 0.35335(11) 0.0316(4) Uani 1 1 d . . .
H14A H -0.0165 0.2300 0.3405 0.038 Uiso 1 1 calc R . .
H14B H 0.1019 0.4223 0.3126 0.038 Uiso 1 1 calc R . .
H14C H 0.1393 0.3838 0.4188 0.038 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 C1 1.2095(18) . ?
O2 C2 1.4261(19) . ?
C1 C5 1.509(2) . ?
C1 C2 1.537(2) . ?
C2 C6 1.519(2) . ?
C2 C3 1.549(2) . ?
C3 C7 1.546(2) . ?
C3 C4 1.553(2) . ?
C4 C5 1.550(2) . ?
C4 C10 1.5511(19) . ?
C5 C13 1.527(2) . ?
C5 C14 1.542(2) . ?
C7 C9 1.523(2) . ?
C7 C8 1.527(2) . ?
C10 C12 1.527(2) . ?
C10 C11 1.531(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
O1 C1 C5 125.03(14) . . ?
O1 C1 C2 123.59(13) . . ?
C5 C1 C2 111.36(12) . . ?
O2 C2 C6 111.29(13) . . ?
O2 C2 C1 105.23(12) . . ?
C6 C2 C1 110.36(13) . . ?
O2 C2 C3 109.71(12) . . ?
C6 C2 C3 115.92(13) . . ?
C1 C2 C3 103.55(11) . . ?
C7 C3 C2 118.66(12) . . ?
C7 C3 C4 115.30(12) . . ?
C2 C3 C4 104.23(11) . . ?
C5 C4 C10 114.26(12) . . ?
C5 C4 C3 104.51(11) . . ?
C10 C4 C3 118.44(12) . . ?
C1 C5 C13 111.94(13) . . ?
C1 C5 C14 105.55(12) . . ?
C13 C5 C14 109.38(13) . . ?
C1 C5 C4 102.17(11) . . ?
C13 C5 C4 113.01(12) . . ?
C14 C5 C4 114.39(12) . . ?
C9 C7 C8 109.84(14) . . ?
C9 C7 C3 112.16(13) . . ?
C8 C7 C3 116.65(13) . . ?
C12 C10 C11 109.94(13) . . ?
C12 C10 C4 115.50(12) . . ?
C11 C10 C4 112.12(13) . . ?

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
O1 C1 C2 O2 -66.50(19) . . . . ?
C5 C1 C2 O2 111.83(13) . . . . ?
O1 C1 C2 C6 53.7(2) . . . . ?
C5 C1 C2 C6 -128.01(14) . . . . ?
O1 C1 C2 C3 178.33(15) . . . . ?
C5 C1 C2 C3 -3.33(15) . . . . ?
O2 C2 C3 C7 42.79(17) . . . . ?
C6 C2 C3 C7 -84.28(18) . . . . ?
C1 C2 C3 C7 154.72(13) . . . . ?
O2 C2 C3 C4 -87.07(14) . . . . ?
C6 C2 C3 C4 145.86(13) . . . . ?
C1 C2 C3 C4 24.86(14) . . . . ?
C7 C3 C4 C5 -169.51(12) . . . . ?
C2 C3 C4 C5 -37.67(14) . . . . ?
C7 C3 C4 C10 61.96(17) . . . . ?
C2 C3 C4 C10 -166.19(12) . . . . ?
O1 C1 C5 C13 37.7(2) . . . . ?
C2 C1 C5 C13 -140.62(13) . . . . ?
O1 C1 C5 C14 -81.22(19) . . . . ?
C2 C1 C5 C14 100.47(14) . . . . ?
O1 C1 C5 C4 158.88(15) . . . . ?
C2 C1 C5 C4 -19.42(15) . . . . ?
C10 C4 C5 C1 165.60(12) . . . . ?
C3 C4 C5 C1 34.59(14) . . . . ?
C10 C4 C5 C13 -73.94(16) . . . . ?
C3 C4 C5 C13 155.05(12) . . . . ?
C10 C4 C5 C14 52.09(17) . . . . ?
C3 C4 C5 C14 -78.92(14) . . . . ?
C2 C3 C7 C9 63.71(18) . . . . ?
C4 C3 C7 C9 -171.67(13) . . . . ?
C2 C3 C7 C8 -64.20(19) . . . . ?
C4 C3 C7 C8 60.42(18) . . . . ?
C5 C4 C10 C12 -92.10(16) . . . . ?
C3 C4 C10 C12 31.72(19) . . . . ?
C5 C4 C10 C11 140.90(13) . . . . ?
C3 C4 C10 C11 -95.27(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.85(2) 2.01(3) 2.8449(18) 166(2) 2_656

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041

_database_code_depnum_ccdc_archive 'CCDC 993485'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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 
#  to carry out CIF format checking respectively.
#
data_5g

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
6-hydroxy-6,7a-dimethyl-5-phenylhexahydrocyclopenta[b]pyran-7(2H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32

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 c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   22.5160(6)
_cell_length_b                   5.6843(2)
_cell_length_c                   21.2628(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2721.38(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7352
_cell_measurement_theta_min      4.16
_cell_measurement_theta_max      71.08

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.6390
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17179
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         71.32
_reflns_number_total             5270
_reflns_number_gt                5028
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_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)+(0.0415P)²+0.7502P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.34(17)
_refine_ls_number_reflns         5270
_refine_ls_number_parameters     351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O1A O 0.13775(6) 0.1773(3) 0.41238(7) 0.0244(3) Uani 1 1 d . . .
O2A O 0.20234(7) 0.3505(3) 0.25521(7) 0.0261(3) Uani 1 1 d . . .
H2OA H 0.1838(17) 0.356(6) 0.2159(19) 0.058(10) Uiso 1 1 d . . .
O3A O 0.08793(7) 0.1349(3) 0.28551(8) 0.0304(3) Uani 1 1 d . . .
C1A C 0.15979(10) 0.1476(5) 0.47519(10) 0.0302(5) Uani 1 1 d . . .
H1AA H 0.1367 0.0229 0.4966 0.036 Uiso 1 1 calc R . .
H1BA H 0.1541 0.2958 0.4989 0.036 Uiso 1 1 calc R . .
C2A C 0.22508(9) 0.0819(5) 0.47590(10) 0.0309(5) Uani 1 1 d . . .
H2AA H 0.2383 0.0554 0.5197 0.037 Uiso 1 1 calc R . .
H2BA H 0.2489 0.2122 0.4581 0.037 Uiso 1 1 calc R . .
C3A C 0.23484(9) -0.1410(4) 0.43730(10) 0.0290(5) Uani 1 1 d . . .
H3AA H 0.2164 -0.2764 0.4592 0.035 Uiso 1 1 calc R . .
H3BA H 0.2780 -0.1721 0.4336 0.035 Uiso 1 1 calc R . .
C4A C 0.20782(9) -0.1165(4) 0.37155(9) 0.0203(4) Uani 1 1 d . . .
H4A H 0.2089 -0.2733 0.3502 0.024 Uiso 1 1 calc R . .
C5A C 0.23993(8) 0.0649(3) 0.32966(8) 0.0176(4) Uani 1 1 d . . .
H5A H 0.2424 0.2134 0.3548 0.021 Uiso 1 1 calc R . .
C6A C 0.19560(8) 0.1135(3) 0.27562(9) 0.0186(4) Uani 1 1 d . . .
C7A C 0.13537(8) 0.0808(3) 0.30814(9) 0.0191(4) Uani 1 1 d . . .
C8A C 0.14330(8) -0.0284(4) 0.37324(10) 0.0203(4) Uani 1 1 d . . .
C9A C 0.30313(8) 0.0003(4) 0.31246(9) 0.0186(4) Uani 1 1 d . . .
C10A C 0.31889(9) -0.2127(4) 0.28533(9) 0.0229(4) Uani 1 1 d . . .
H10A H 0.2890 -0.3262 0.2766 0.027 Uiso 1 1 calc R . .
C11A C 0.37826(9) -0.2629(4) 0.27061(11) 0.0278(4) Uani 1 1 d . . .
H11A H 0.3882 -0.4079 0.2510 0.033 Uiso 1 1 calc R . .
C12A C 0.42243(9) -0.1012(4) 0.28459(10) 0.0279(5) Uani 1 1 d . . .
H12A H 0.4627 -0.1353 0.2751 0.033 Uiso 1 1 calc R . .
C13A C 0.40733(10) 0.1095(4) 0.31233(11) 0.0300(5) Uani 1 1 d . . .
H13A H 0.4374 0.2204 0.3224 0.036 Uiso 1 1 calc R . .
C14A C 0.34812(9) 0.1611(4) 0.32574(10) 0.0245(4) Uani 1 1 d . . .
H14A H 0.3383 0.3082 0.3442 0.029 Uiso 1 1 calc R . .
C15A C 0.19833(9) -0.0548(4) 0.22048(9) 0.0256(4) Uani 1 1 d . . .
H15A H 0.1687 -0.0091 0.1890 0.031 Uiso 1 1 calc R . .
H15B H 0.1900 -0.2150 0.2351 0.031 Uiso 1 1 calc R . .
H15C H 0.2380 -0.0493 0.2016 0.031 Uiso 1 1 calc R . .
C16A C 0.09646(10) -0.2112(4) 0.38852(11) 0.0308(5) Uani 1 1 d . . .
H16A H 0.0572 -0.1371 0.3884 0.037 Uiso 1 1 calc R . .
H16B H 0.1044 -0.2782 0.4302 0.037 Uiso 1 1 calc R . .
H16C H 0.0976 -0.3365 0.3569 0.037 Uiso 1 1 calc R . .
O1B O 0.11030(6) 0.5193(3) 0.00787(7) 0.0296(3) Uani 1 1 d . . .
O2B O 0.04366(7) 0.2376(3) 0.16236(7) 0.0248(3) Uani 1 1 d . . .
H2OB H 0.0589(16) 0.232(6) 0.201(2) 0.062(11) Uiso 1 1 d . . .
O3B O 0.15420(6) 0.4802(3) 0.13657(8) 0.0294(3) Uani 1 1 d . . .
C1B C 0.08995(11) 0.5872(5) -0.05352(11) 0.0384(6) Uani 1 1 d . . .
H1AB H 0.1012 0.4644 -0.0843 0.046 Uiso 1 1 calc R . .
H1BB H 0.1097 0.7356 -0.0660 0.046 Uiso 1 1 calc R . .
C2B C 0.02325(11) 0.6214(5) -0.05506(10) 0.0371(6) Uani 1 1 d . . .
H2AB H 0.0031 0.4705 -0.0458 0.045 Uiso 1 1 calc R . .
H2BB H 0.0109 0.6737 -0.0975 0.045 Uiso 1 1 calc R . .
C3B C 0.00538(9) 0.8046(4) -0.00655(10) 0.0292(5) Uani 1 1 d . . .
H3AB H -0.0385 0.8123 -0.0040 0.035 Uiso 1 1 calc R . .
H3BB H 0.0200 0.9610 -0.0200 0.035 Uiso 1 1 calc R . .
C4B C 0.03061(8) 0.7461(3) 0.05831(9) 0.0192(4) Uani 1 1 d . . .
H4B H 0.0247 0.8856 0.0863 0.023 Uiso 1 1 calc R . .
C5B C 0.00298(8) 0.5286(3) 0.09080(9) 0.0179(4) Uani 1 1 d . . .
H5B H 0.0070 0.3943 0.0607 0.021 Uiso 1 1 calc R . .
C6B C 0.04606(8) 0.4789(3) 0.14589(9) 0.0191(4) Uani 1 1 d . . .
C7B C 0.10618(8) 0.5420(3) 0.11586(9) 0.0195(4) Uani 1 1 d . . .
C8B C 0.09756(8) 0.6888(4) 0.05614(9) 0.0211(4) Uani 1 1 d . . .
C9B C -0.06243(8) 0.5489(4) 0.10671(9) 0.0196(4) Uani 1 1 d . . .
C10B C -0.08613(9) 0.7479(4) 0.13570(10) 0.0245(4) Uani 1 1 d . . .
H10B H -0.0609 0.8760 0.1462 0.029 Uiso 1 1 calc R . .
C11B C -0.14646(10) 0.7601(4) 0.14941(11) 0.0305(5) Uani 1 1 d . . .
H11B H -0.1621 0.8946 0.1701 0.037 Uiso 1 1 calc R . .
C12B C -0.18374(9) 0.5760(5) 0.13289(11) 0.0329(5) Uani 1 1 d . . .
H12B H -0.2250 0.5853 0.1417 0.039 Uiso 1 1 calc R . .
C13B C -0.16087(10) 0.3796(4) 0.10370(11) 0.0319(5) Uani 1 1 d . . .
H13B H -0.1864 0.2535 0.0923 0.038 Uiso 1 1 calc R . .
C14B C -0.10043(9) 0.3660(4) 0.09090(10) 0.0248(4) Uani 1 1 d . . .
H14B H -0.0849 0.2295 0.0710 0.030 Uiso 1 1 calc R . .
C15B C 0.03758(9) 0.6322(4) 0.20396(9) 0.0239(4) Uani 1 1 d . . .
H15D H 0.0667 0.5879 0.2361 0.029 Uiso 1 1 calc R . .
H15E H -0.0026 0.6096 0.2206 0.029 Uiso 1 1 calc R . .
H15F H 0.0431 0.7979 0.1926 0.029 Uiso 1 1 calc R . .
C16B C 0.13857(9) 0.8991(4) 0.05295(11) 0.0292(5) Uani 1 1 d . . .
H16D H 0.1799 0.8451 0.0518 0.035 Uiso 1 1 calc R . .
H16E H 0.1325 0.9983 0.0901 0.035 Uiso 1 1 calc R . .
H16F H 0.1299 0.9902 0.0149 0.035 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
O1A C1A 1.435(2) . ?
O1A C8A 1.441(3) . ?
O2A C6A 1.423(2) . ?
O3A C7A 1.211(2) . ?
C1A C2A 1.517(3) . ?
C2A C3A 1.526(3) . ?
C3A C4A 1.531(3) . ?
C4A C8A 1.537(2) . ?
C4A C5A 1.543(3) . ?
C5A C9A 1.515(2) . ?
C5A C6A 1.547(2) . ?
C6A C15A 1.515(3) . ?
C6A C7A 1.534(2) . ?
C7A C8A 1.528(3) . ?
C8A C16A 1.516(3) . ?
C9A C10A 1.387(3) . ?
C9A C14A 1.393(3) . ?
C10A C11A 1.402(3) . ?
C11A C12A 1.387(3) . ?
C12A C13A 1.378(3) . ?
C13A C14A 1.394(3) . ?
O1B C1B 1.436(3) . ?
O1B C8B 1.437(2) . ?
O2B C6B 1.416(2) . ?
O3B C7B 1.219(2) . ?
C1B C2B 1.515(3) . ?
C2B C3B 1.520(3) . ?
C3B C4B 1.528(3) . ?
C4B C8B 1.543(2) . ?
C4B C5B 1.547(3) . ?
C5B C9B 1.516(3) . ?
C5B C6B 1.547(3) . ?
C6B C15B 1.523(3) . ?
C6B C7B 1.539(2) . ?
C7B C8B 1.532(3) . ?
C8B C16B 1.512(3) . ?
C9B C14B 1.388(3) . ?
C9B C10B 1.394(3) . ?
C10B C11B 1.391(3) . ?
C11B C12B 1.387(4) . ?
C12B C13B 1.377(4) . ?
C13B C14B 1.390(3) . ?

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
C1A O1A C8A 114.34(16) . . ?
O1A C1A C2A 111.93(17) . . ?
C1A C2A C3A 109.81(19) . . ?
C2A C3A C4A 111.01(17) . . ?
C3A C4A C8A 112.56(17) . . ?
C3A C4A C5A 113.68(17) . . ?
C8A C4A C5A 103.79(15) . . ?
C9A C5A C4A 114.67(16) . . ?
C9A C5A C6A 118.04(15) . . ?
C4A C5A C6A 104.23(15) . . ?
O2A C6A C15A 110.95(16) . . ?
O2A C6A C7A 110.27(16) . . ?
C15A C6A C7A 107.96(16) . . ?
O2A C6A C5A 109.06(15) . . ?
C15A C6A C5A 115.86(16) . . ?
C7A C6A C5A 102.36(15) . . ?
O3A C7A C8A 124.49(18) . . ?
O3A C7A C6A 124.76(18) . . ?
C8A C7A C6A 110.75(15) . . ?
O1A C8A C16A 111.85(17) . . ?
O1A C8A C7A 100.57(15) . . ?
C16A C8A C7A 113.04(17) . . ?
O1A C8A C4A 111.11(16) . . ?
C16A C8A C4A 116.05(17) . . ?
C7A C8A C4A 102.81(15) . . ?
C10A C9A C14A 118.09(19) . . ?
C10A C9A C5A 123.54(17) . . ?
C14A C9A C5A 118.36(18) . . ?
C9A C10A C11A 120.94(19) . . ?
C12A C11A C10A 120.1(2) . . ?
C13A C12A C11A 119.43(19) . . ?
C12A C13A C14A 120.4(2) . . ?
C9A C14A C13A 121.1(2) . . ?
C1B O1B C8B 113.93(18) . . ?
O1B C1B C2B 111.75(18) . . ?
C1B C2B C3B 109.62(19) . . ?
C2B C3B C4B 111.40(18) . . ?
C3B C4B C8B 112.46(16) . . ?
C3B C4B C5B 115.31(16) . . ?
C8B C4B C5B 103.75(15) . . ?
C9B C5B C4B 115.43(16) . . ?
C9B C5B C6B 117.02(15) . . ?
C4B C5B C6B 103.40(15) . . ?
O2B C6B C15B 110.42(16) . . ?
O2B C6B C7B 111.21(15) . . ?
C15B C6B C7B 108.26(16) . . ?
O2B C6B C5B 109.87(15) . . ?
C15B C6B C5B 115.51(16) . . ?
C7B C6B C5B 101.24(15) . . ?
O3B C7B C8B 124.65(17) . . ?
O3B C7B C6B 124.28(18) . . ?
C8B C7B C6B 111.06(15) . . ?
O1B C8B C16B 112.09(17) . . ?
O1B C8B C7B 101.63(15) . . ?
C16B C8B C7B 112.99(16) . . ?
O1B C8B C4B 110.98(16) . . ?
C16B C8B C4B 115.55(17) . . ?
C7B C8B C4B 102.35(15) . . ?
C14B C9B C10B 118.61(18) . . ?
C14B C9B C5B 119.19(18) . . ?
C10B C9B C5B 122.19(18) . . ?
C11B C10B C9B 120.5(2) . . ?
C12B C11B C10B 120.0(2) . . ?
C13B C12B C11B 120.0(2) . . ?
C12B C13B C14B 120.0(2) . . ?
C9B C14B C13B 120.9(2) . . ?

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
C8A O1A C1A C2A 59.3(3) . . . . ?
O1A C1A C2A C3A -56.7(3) . . . . ?
C1A C2A C3A C4A 52.2(2) . . . . ?
C2A C3A C4A C8A -49.7(2) . . . . ?
C2A C3A C4A C5A 67.9(2) . . . . ?
C3A C4A C5A C9A 65.7(2) . . . . ?
C8A C4A C5A C9A -171.68(16) . . . . ?
C3A C4A C5A C6A -163.74(16) . . . . ?
C8A C4A C5A C6A -41.12(19) . . . . ?
C9A C5A C6A O2A -83.3(2) . . . . ?
C4A C5A C6A O2A 148.19(15) . . . . ?
C9A C5A C6A C15A 42.7(2) . . . . ?
C4A C5A C6A C15A -85.81(19) . . . . ?
C9A C5A C6A C7A 159.92(16) . . . . ?
C4A C5A C6A C7A 31.39(19) . . . . ?
O2A C6A C7A O3A 52.9(3) . . . . ?
C15A C6A C7A O3A -68.5(3) . . . . ?
C5A C6A C7A O3A 168.8(2) . . . . ?
O2A C6A C7A C8A -126.81(17) . . . . ?
C15A C6A C7A C8A 111.83(18) . . . . ?
C5A C6A C7A C8A -10.9(2) . . . . ?
C1A O1A C8A C16A 76.8(2) . . . . ?
C1A O1A C8A C7A -162.93(16) . . . . ?
C1A O1A C8A C4A -54.6(2) . . . . ?
O3A C7A C8A O1A -78.8(2) . . . . ?
C6A C7A C8A O1A 100.90(17) . . . . ?
O3A C7A C8A C16A 40.6(3) . . . . ?
C6A C7A C8A C16A -139.70(18) . . . . ?
O3A C7A C8A C4A 166.5(2) . . . . ?
C6A C7A C8A C4A -13.8(2) . . . . ?
C3A C4A C8A O1A 49.7(2) . . . . ?
C5A C4A C8A O1A -73.68(19) . . . . ?
C3A C4A C8A C16A -79.6(2) . . . . ?
C5A C4A C8A C16A 157.06(18) . . . . ?
C3A C4A C8A C7A 156.50(18) . . . . ?
C5A C4A C8A C7A 33.15(19) . . . . ?
C4A C5A C9A C10A 53.1(2) . . . . ?
C6A C5A C9A C10A -70.3(2) . . . . ?
C4A C5A C9A C14A -125.5(2) . . . . ?
C6A C5A C9A C14A 111.1(2) . . . . ?
C14A C9A C10A C11A -1.2(3) . . . . ?
C5A C9A C10A C11A -179.80(18) . . . . ?
C9A C10A C11A C12A 1.6(3) . . . . ?
C10A C11A C12A C13A -0.7(3) . . . . ?
C11A C12A C13A C14A -0.6(3) . . . . ?
C10A C9A C14A C13A -0.2(3) . . . . ?
C5A C9A C14A C13A 178.53(18) . . . . ?
C12A C13A C14A C9A 1.1(3) . . . . ?
C8B O1B C1B C2B -60.4(3) . . . . ?
O1B C1B C2B C3B 57.3(3) . . . . ?
C1B C2B C3B C4B -52.1(3) . . . . ?
C2B C3B C4B C8B 49.1(2) . . . . ?
C2B C3B C4B C5B -69.6(2) . . . . ?
C3B C4B C5B C9B -63.8(2) . . . . ?
C8B C4B C5B C9B 172.74(15) . . . . ?
C3B C4B C5B C6B 167.08(16) . . . . ?
C8B C4B C5B C6B 43.65(18) . . . . ?
C9B C5B C6B O2B 78.1(2) . . . . ?
C4B C5B C6B O2B -153.80(15) . . . . ?
C9B C5B C6B C15B -47.6(2) . . . . ?
C4B C5B C6B C15B 80.51(19) . . . . ?
C9B C5B C6B C7B -164.26(16) . . . . ?
C4B C5B C6B C7B -36.16(17) . . . . ?
O2B C6B C7B O3B -45.7(3) . . . . ?
C15B C6B C7B O3B 75.7(2) . . . . ?
C5B C6B C7B O3B -162.39(19) . . . . ?
O2B C6B C7B C8B 133.38(16) . . . . ?
C15B C6B C7B C8B -105.15(18) . . . . ?
C5B C6B C7B C8B 16.72(19) . . . . ?
C1B O1B C8B C16B -75.6(2) . . . . ?
C1B O1B C8B C7B 163.49(17) . . . . ?
C1B O1B C8B C4B 55.3(2) . . . . ?
O3B C7B C8B O1B 73.6(2) . . . . ?
C6B C7B C8B O1B -105.45(17) . . . . ?
O3B C7B C8B C16B -46.6(3) . . . . ?
C6B C7B C8B C16B 134.26(18) . . . . ?
O3B C7B C8B C4B -171.56(19) . . . . ?
C6B C7B C8B C4B 9.3(2) . . . . ?
C3B C4B C8B O1B -49.4(2) . . . . ?
C5B C4B C8B O1B 75.86(19) . . . . ?
C3B C4B C8B C16B 79.6(2) . . . . ?
C5B C4B C8B C16B -155.12(17) . . . . ?
C3B C4B C8B C7B -157.18(17) . . . . ?
C5B C4B C8B C7B -31.90(18) . . . . ?
C4B C5B C9B C14B 132.15(19) . . . . ?
C6B C5B C9B C14B -105.8(2) . . . . ?
C4B C5B C9B C10B -46.5(2) . . . . ?
C6B C5B C9B C10B 75.5(2) . . . . ?
C14B C9B C10B C11B 1.2(3) . . . . ?
C5B C9B C10B C11B 179.85(18) . . . . ?
C9B C10B C11B C12B -1.5(3) . . . . ?
C10B C11B C12B C13B 0.9(3) . . . . ?
C11B C12B C13B C14B 0.1(3) . . . . ?
C10B C9B C14B C13B -0.2(3) . . . . ?
C5B C9B C14B C13B -178.89(18) . . . . ?
C12B C13B C14B C9B -0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2A H2OA O3B 0.94(4) 1.95(4) 2.843(2) 160(3) .
O2B H2OB O3A 0.89(4) 2.00(4) 2.862(2) 166(3) .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        71.32
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051


#===END
_database_code_depnum_ccdc_archive 'CCDC 993486'
