# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_bredikh_sm48fin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26

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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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                   4.984(4)
_cell_length_b                   7.525(5)
_cell_length_c                   31.24(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.611(10)
_cell_angle_gamma                90.00
_cell_volume                     1170.4(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14379
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         28.00
_reflns_number_total             2807
_reflns_number_gt                1972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0437P)²+0.2593P] 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         2807
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.6730(3) 0.18100(19) 0.19801(5) 0.0233(3) Uani 1 1 d . . .
H11 H 0.5839 0.1496 0.1701 0.028 Uiso 1 1 calc R . .
H12 H 0.7940 0.0819 0.2068 0.028 Uiso 1 1 calc R . .
C2 C 0.8371(3) 0.34856(19) 0.19301(5) 0.0206(3) Uani 1 1 d . . .
H20 H 0.9530 0.3333 0.1680 0.025 Uiso 1 1 calc R . .
C3 C 0.6656(3) 0.51357(19) 0.18575(5) 0.0215(3) Uani 1 1 d . . .
H31 H 0.5645 0.5403 0.2115 0.026 Uiso 1 1 calc R . .
H32 H 0.7798 0.6172 0.1795 0.026 Uiso 1 1 calc R . .
C4 C 0.3135(3) 0.61138(19) 0.13640(5) 0.0213(3) Uani 1 1 d . . .
C5 C 0.1356(3) 0.5688(2) 0.10186(5) 0.0248(3) Uani 1 1 d . . .
C6 C -0.0409(3) 0.7005(2) 0.08690(5) 0.0316(4) Uani 1 1 d . . .
H6 H -0.1633 0.6746 0.0635 0.038 Uiso 1 1 calc R . .
C7 C -0.0430(3) 0.8688(2) 0.10517(6) 0.0350(4) Uani 1 1 d . . .
H7 H -0.1647 0.9568 0.0943 0.042 Uiso 1 1 calc R . .
C8 C 0.1332(3) 0.9068(2) 0.13919(5) 0.0298(4) Uani 1 1 d . . .
H8 H 0.1331 1.0219 0.1517 0.036 Uiso 1 1 calc R . .
C9 C 0.3116(3) 0.7785(2) 0.15546(5) 0.0246(3) Uani 1 1 d . . .
H9 H 0.4304 0.8047 0.1793 0.030 Uiso 1 1 calc R . .
C10 C 0.1411(3) 0.3876(2) 0.08088(5) 0.0302(4) Uani 1 1 d . . .
H13 H 0.2000 0.2982 0.1026 0.036 Uiso 1 1 calc R . .
H14 H -0.0431 0.3559 0.0704 0.036 Uiso 1 1 calc R . .
C11 C 0.3259(4) 0.3799(2) 0.04390(6) 0.0411(5) Uani 1 1 d . . .
H15 H 0.5066 0.4212 0.0539 0.049 Uiso 1 1 calc R . .
H16 H 0.2582 0.4621 0.0212 0.049 Uiso 1 1 calc R . .
C12 C 0.3496(5) 0.1942(3) 0.02497(7) 0.0553(6) Uani 1 1 d . . .
H17 H 0.4188 0.1122 0.0472 0.083 Uiso 1 1 calc R . .
H18 H 0.4728 0.1971 0.0014 0.083 Uiso 1 1 calc R . .
H19 H 0.1723 0.1539 0.0141 0.083 Uiso 1 1 calc R . .
O1 O 0.4747(2) 0.20321(15) 0.22909(4) 0.0303(3) Uani 1 1 d . . .
O2 O 1.0068(2) 0.38502(14) 0.23037(3) 0.0249(3) Uani 1 1 d . . .
O3 O 0.4847(2) 0.47659(13) 0.15007(3) 0.0251(3) Uani 1 1 d . . .
H1 H 0.463(4) 0.109(3) 0.2441(7) 0.057(7) Uiso 1 1 d . . .
H2 H 1.163(4) 0.328(3) 0.2284(6) 0.051(6) Uiso 1 1 d . . .


_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 1.4265(19) . ?
C1 C2 1.515(2) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 O2 1.4360(19) . ?
C2 C3 1.519(2) . ?
C2 H20 1.0000 . ?
C3 O3 1.4283(19) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O3 1.3807(18) . ?
C4 C9 1.392(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.392(2) . ?
C5 C10 1.514(2) . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.511(2) . ?
C10 H13 0.9900 . ?
C10 H14 0.9900 . ?
C11 C12 1.524(3) . ?
C11 H15 0.9900 . ?
C11 H16 0.9900 . ?
C12 H17 0.9800 . ?
C12 H18 0.9800 . ?
C12 H19 0.9800 . ?
O1 H1 0.85(2) . ?
O2 H2 0.89(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 C2 111.51(12) . . ?
O1 C1 H11 109.3 . . ?
C2 C1 H11 109.3 . . ?
O1 C1 H12 109.3 . . ?
C2 C1 H12 109.3 . . ?
H11 C1 H12 108.0 . . ?
O2 C2 C1 112.08(12) . . ?
O2 C2 C3 105.77(12) . . ?
C1 C2 C3 113.13(13) . . ?
O2 C2 H20 108.6 . . ?
C1 C2 H20 108.6 . . ?
C3 C2 H20 108.6 . . ?
O3 C3 C2 106.76(12) . . ?
O3 C3 H31 110.4 . . ?
C2 C3 H31 110.4 . . ?
O3 C3 H32 110.4 . . ?
C2 C3 H32 110.4 . . ?
H31 C3 H32 108.6 . . ?
O3 C4 C9 123.21(14) . . ?
O3 C4 C5 115.51(13) . . ?
C9 C4 C5 121.27(14) . . ?
C6 C5 C4 117.63(15) . . ?
C6 C5 C10 121.32(15) . . ?
C4 C5 C10 121.03(14) . . ?
C7 C6 C5 121.85(16) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 119.31(15) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.76(16) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 119.16(15) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C5 112.90(14) . . ?
C11 C10 H13 109.0 . . ?
C5 C10 H13 109.0 . . ?
C11 C10 H14 109.0 . . ?
C5 C10 H14 109.0 . . ?
H13 C10 H14 107.8 . . ?
C10 C11 C12 113.11(16) . . ?
C10 C11 H15 109.0 . . ?
C12 C11 H15 109.0 . . ?
C10 C11 H16 109.0 . . ?
C12 C11 H16 109.0 . . ?
H15 C11 H16 107.8 . . ?
C11 C12 H17 109.5 . . ?
C11 C12 H18 109.5 . . ?
H17 C12 H18 109.5 . . ?
C11 C12 H19 109.5 . . ?
H17 C12 H19 109.5 . . ?
H18 C12 H19 109.5 . . ?
C1 O1 H1 110.3(14) . . ?
C2 O2 H2 109.4(13) . . ?
C4 O3 C3 117.22(11) . . ?

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 68.72(16) . . . . ?
O1 C1 C2 C3 -50.77(17) . . . . ?
O2 C2 C3 O3 -176.90(11) . . . . ?
C1 C2 C3 O3 -53.84(16) . . . . ?
O3 C4 C5 C6 -179.94(13) . . . . ?
C9 C4 C5 C6 0.8(2) . . . . ?
O3 C4 C5 C10 -1.6(2) . . . . ?
C9 C4 C5 C10 179.19(14) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C10 C5 C6 C7 -178.29(15) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
O3 C4 C9 C8 179.39(13) . . . . ?
C5 C4 C9 C8 -1.4(2) . . . . ?
C7 C8 C9 C4 1.2(2) . . . . ?
C6 C5 C10 C11 87.6(2) . . . . ?
C4 C5 C10 C11 -90.73(19) . . . . ?
C5 C10 C11 C12 175.36(16) . . . . ?
C9 C4 O3 C3 0.4(2) . . . . ?
C5 C4 O3 C3 -178.80(12) . . . . ?
C2 C3 O3 C4 -177.66(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 983812'
#######################################################################
#
#                 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_bredikh_sm9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 O3'
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_weight         196.24

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           Orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   5.0871(13)
_cell_length_b                   7.5857(19)
_cell_length_c                   26.719(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1031.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2214
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      26.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   7
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;


_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_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5567
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2324
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;
_chemical_absolute_configuration rm
_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)+(0.0459P)²+0.2905P] 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         2324
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 -0.2531(3) 0.52133(19) 0.77294(6) 0.0415(4) Uani 1 1 d . . .
O1 O 0.2723(3) 0.6978(2) 0.77443(7) 0.0492(4) Uani 1 1 d . . .
C3 C 0.0663(4) 0.3917(3) 0.82466(8) 0.0347(4) Uani 1 1 d . . .
C2 C -0.0966(4) 0.5562(3) 0.81624(7) 0.0314(4) Uani 1 1 d . . .
C1 C 0.0682(4) 0.7204(3) 0.81050(9) 0.0388(5) Uani 1 1 d . . .
O3 O 0.2290(3) 0.42438(19) 0.86694(5) 0.0401(4) Uani 1 1 d . . .
C5 C 0.5647(4) 0.3353(3) 0.92151(7) 0.0342(4) Uani 1 1 d . . .
C9 C 0.4096(5) 0.1297(3) 0.85821(9) 0.0411(5) Uani 1 1 d . . .
C10 C 0.5402(4) 0.5128(3) 0.94649(8) 0.0410(5) Uani 1 1 d . . .
C8 C 0.5897(5) 0.0051(3) 0.87498(9) 0.0473(5) Uani 1 1 d . . .
C4 C 0.3980(4) 0.2932(3) 0.88140(7) 0.0339(4) Uani 1 1 d . . .
C7 C 0.7564(5) 0.0437(3) 0.91387(9) 0.0490(5) Uani 1 1 d . . .
C6 C 0.7436(5) 0.2076(3) 0.93681(8) 0.0442(5) Uani 1 1 d . . .
C11 C 0.7645(6) 0.5656(5) 0.98017(14) 0.0653(8) Uani 1 1 d . . .
H2 H -0.408(6) 0.566(4) 0.7741(9) 0.053(7) Uiso 1 1 d . . .
H20 H -0.224(4) 0.579(3) 0.8468(7) 0.039(6) Uiso 1 1 d . . .
H32 H -0.048(5) 0.290(3) 0.8299(8) 0.049(6) Uiso 1 1 d . . .
H31 H 0.178(5) 0.372(3) 0.7953(9) 0.050(7) Uiso 1 1 d . . .
H9 H 0.300(5) 0.103(3) 0.8309(9) 0.052(7) Uiso 1 1 d . . .
H6 H 0.872(5) 0.240(4) 0.9638(9) 0.056(7) Uiso 1 1 d . . .
H1 H 0.283(6) 0.788(4) 0.7580(10) 0.059(8) Uiso 1 1 d . . .
H12 H 0.152(5) 0.743(3) 0.8451(9) 0.054(7) Uiso 1 1 d . . .
H11 H -0.048(5) 0.815(4) 0.8007(9) 0.058(7) Uiso 1 1 d . . .
H8 H 0.594(6) -0.108(4) 0.8581(9) 0.060(7) Uiso 1 1 d . . .
H7 H 0.886(6) -0.046(4) 0.9255(9) 0.067(8) Uiso 1 1 d . . .
H14 H 0.368(5) 0.513(3) 0.9668(9) 0.055(7) Uiso 1 1 d . . .
H13 H 0.515(4) 0.602(3) 0.9206(9) 0.047(7) Uiso 1 1 d . . .
H15 H 0.735(6) 0.685(4) 0.9938(11) 0.072(9) Uiso 1 1 d . . .
H16 H 0.926(7) 0.572(4) 0.9583(11) 0.078(9) Uiso 1 1 d . . .
H17 H 0.790(7) 0.487(5) 1.0066(13) 0.096(13) Uiso 1 1 d . . .


_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 C2 1.429(2) . ?
O2 H2 0.86(3) . ?
O1 C1 1.427(3) . ?
O1 H1 0.81(3) . ?
C3 O3 1.422(2) . ?
C3 C2 1.515(3) . ?
C3 H32 0.97(3) . ?
C3 H31 0.98(2) . ?
C2 C1 1.510(3) . ?
C2 H20 1.06(2) . ?
C1 H12 1.03(3) . ?
C1 H11 0.97(3) . ?
O3 C4 1.371(2) . ?
C5 C6 1.391(3) . ?
C5 C4 1.403(3) . ?
C5 C10 1.508(3) . ?
C9 C4 1.388(3) . ?
C9 C8 1.391(3) . ?
C9 H9 0.94(2) . ?
C10 C11 1.507(3) . ?
C10 H14 1.03(3) . ?
C10 H13 0.98(3) . ?
C8 C7 1.373(3) . ?
C8 H8 0.97(3) . ?
C7 C6 1.387(3) . ?
C7 H7 0.99(3) . ?
C6 H6 1.00(2) . ?
C11 H15 0.99(3) . ?
C11 H16 1.01(3) . ?
C11 H17 0.93(4) . ?

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 O2 H2 114.1(16) . . ?
C1 O1 H1 108(2) . . ?
O3 C3 C2 107.02(16) . . ?
O3 C3 H32 111.7(13) . . ?
C2 C3 H32 110.2(15) . . ?
O3 C3 H31 108.9(14) . . ?
C2 C3 H31 108.8(15) . . ?
H32 C3 H31 110(2) . . ?
O2 C2 C1 112.32(16) . . ?
O2 C2 C3 105.83(15) . . ?
C1 C2 C3 113.03(16) . . ?
O2 C2 H20 108.4(11) . . ?
C1 C2 H20 106.5(12) . . ?
C3 C2 H20 110.7(12) . . ?
O1 C1 C2 111.92(18) . . ?
O1 C1 H12 109.0(14) . . ?
C2 C1 H12 105.8(15) . . ?
O1 C1 H11 110.7(15) . . ?
C2 C1 H11 107.4(17) . . ?
H12 C1 H11 112(2) . . ?
C4 O3 C3 117.54(15) . . ?
C6 C5 C4 117.48(19) . . ?
C6 C5 C10 123.1(2) . . ?
C4 C5 C10 119.40(18) . . ?
C4 C9 C8 119.5(2) . . ?
C4 C9 H9 121.0(15) . . ?
C8 C9 H9 119.6(15) . . ?
C11 C10 C5 116.0(2) . . ?
C11 C10 H14 109.1(14) . . ?
C5 C10 H14 107.8(15) . . ?
C11 C10 H13 109.9(14) . . ?
C5 C10 H13 108.3(14) . . ?
H14 C10 H13 105.1(19) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 121.8(16) . . ?
C9 C8 H8 117.9(17) . . ?
O3 C4 C9 123.34(18) . . ?
O3 C4 C5 115.42(17) . . ?
C9 C4 C5 121.24(19) . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 119.9(16) . . ?
C6 C7 H7 120.3(16) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 120.5(16) . . ?
C5 C6 H6 117.7(16) . . ?
C10 C11 H15 110.3(18) . . ?
C10 C11 H16 106.5(17) . . ?
H15 C11 H16 107(3) . . ?
C10 C11 H17 113(2) . . ?
H15 C11 H17 109(3) . . ?
H16 C11 H17 111(3) . . ?

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
O3 C3 C2 O2 178.62(15) . . . . ?
O3 C3 C2 C1 55.3(2) . . . . ?
O2 C2 C1 O1 -69.2(2) . . . . ?
C3 C2 C1 O1 50.5(2) . . . . ?
C2 C3 O3 C4 -179.19(16) . . . . ?
C6 C5 C10 C11 15.5(3) . . . . ?
C4 C5 C10 C11 -165.6(2) . . . . ?
C4 C9 C8 C7 -0.6(4) . . . . ?
C3 O3 C4 C9 -2.7(3) . . . . ?
C3 O3 C4 C5 176.57(17) . . . . ?
C8 C9 C4 O3 179.2(2) . . . . ?
C8 C9 C4 C5 0.0(3) . . . . ?
C6 C5 C4 O3 -178.66(18) . . . . ?
C10 C5 C4 O3 2.4(3) . . . . ?
C6 C5 C4 C9 0.6(3) . . . . ?
C10 C5 C4 C9 -178.3(2) . . . . ?
C9 C8 C7 C6 0.5(4) . . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C10 C5 C6 C7 178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 983813'
#######################################################################
#
#                 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_br_39_p21

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26

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_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   5.0077(9)
_cell_length_b                   30.877(6)
_cell_length_c                   7.4685(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.117(2)
_cell_angle_gamma                90.00
_cell_volume                     1154.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9379
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19369
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4995
_reflns_number_gt                4839
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_chemical_absolute_configuration rm
_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)+(0.0714P)²+1.3166P] 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         4995
_refine_ls_number_parameters     287
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1569
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_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
C1A C 0.7114(6) 0.90695(9) 0.5710(4) 0.0179(5) Uani 1 1 d . . .
H11A H 0.5953 0.9160 0.6714 0.022 Uiso 1 1 calc R . .
H12A H 0.7920 0.8787 0.6024 0.022 Uiso 1 1 calc R . .
C2A C 0.5430(5) 0.90209(9) 0.4007(3) 0.0159(5) Uani 1 1 d . . .
H20A H 0.4212 0.8767 0.4157 0.019 Uiso 1 1 calc R . .
C3A C 0.7136(5) 0.89487(9) 0.2332(4) 0.0158(5) Uani 1 1 d . . .
H31A H 0.5988 0.8883 0.1286 0.019 Uiso 1 1 calc R . .
H32A H 0.8203 0.9210 0.2061 0.019 Uiso 1 1 calc R . .
C4A C 1.0507(5) 0.84543(9) 0.1369(4) 0.0160(5) Uani 1 1 d . . .
C5A C 1.2185(6) 0.81032(9) 0.1778(4) 0.0186(5) Uani 1 1 d . . .
C6A C 1.3908(6) 0.79544(10) 0.0487(4) 0.0231(6) Uani 1 1 d . . .
H6A H 1.5068 0.7719 0.0753 0.028 Uiso 1 1 calc R . .
C7A C 1.3979(6) 0.81470(12) -0.1240(4) 0.0263(7) Uani 1 1 d . . .
H7A H 1.5155 0.8040 -0.2134 0.032 Uiso 1 1 calc R . .
C8A C 1.2324(6) 0.84896(10) -0.1596(4) 0.0234(6) Uani 1 1 d . . .
H8A H 1.2368 0.8620 -0.2747 0.028 Uiso 1 1 calc R . .
C9A C 1.0578(6) 0.86507(9) -0.0308(4) 0.0179(5) Uani 1 1 d . . .
H9A H 0.9455 0.8891 -0.0570 0.021 Uiso 1 1 calc R . .
C10A C 1.2048(6) 0.78918(9) 0.3619(4) 0.0215(6) Uani 1 1 d . . .
H13A H 1.3803 0.7761 0.3901 0.026 Uiso 1 1 calc R . .
H14A H 1.1687 0.8118 0.4527 0.026 Uiso 1 1 calc R . .
C11A C 0.9901(8) 0.75437(11) 0.3745(5) 0.0328(7) Uani 1 1 d . . .
H15A H 1.0371 0.7301 0.2940 0.039 Uiso 1 1 calc R . .
H16A H 0.8177 0.7665 0.3333 0.039 Uiso 1 1 calc R . .
C12A C 0.9580(9) 0.73716(13) 0.5653(5) 0.0417(9) Uani 1 1 d . . .
H17A H 1.1271 0.7245 0.6057 0.062 Uiso 1 1 calc R . .
H18A H 0.8181 0.7150 0.5672 0.062 Uiso 1 1 calc R . .
H19A H 0.9082 0.7610 0.6451 0.062 Uiso 1 1 calc R . .
O1A O 0.9182(4) 0.93836(7) 0.5457(3) 0.0219(5) Uani 1 1 d . . .
O2A O 0.3854(4) 0.93947(7) 0.3644(3) 0.0200(4) Uani 1 1 d . . .
O3A O 0.8852(4) 0.85898(7) 0.2726(3) 0.0201(4) Uani 1 1 d . . .
H1A H 0.920(6) 0.9522(11) 0.647(5) 0.010(7) Uiso 1 1 d . . .
H2A H 0.328(12) 0.9484(19) 0.472(9) 0.068(17) Uiso 1 1 d . . .
C1B C 0.5855(5) 0.01181(9) 1.0697(4) 0.0168(5) Uani 1 1 d . . .
H11B H 0.7023 0.0027 1.1700 0.020 Uiso 1 1 calc R . .
H12B H 0.5047 0.0400 1.1016 0.020 Uiso 1 1 calc R . .
C2B C 0.7523(5) 0.01704(9) 0.9015(4) 0.0151(5) Uani 1 1 d . . .
H20B H 0.8730 0.0426 0.9166 0.018 Uiso 1 1 calc R . .
C3B C 0.5823(5) 0.02371(9) 0.7359(4) 0.0160(5) Uani 1 1 d . . .
H31B H 0.6967 0.0300 0.6311 0.019 Uiso 1 1 calc R . .
H32B H 0.4763 -0.0026 0.7102 0.019 Uiso 1 1 calc R . .
C4B C 0.2471(5) 0.07353(9) 0.6345(3) 0.0147(5) Uani 1 1 d . . .
C5B C 0.0878(5) 0.10981(9) 0.6730(4) 0.0179(5) Uani 1 1 d . . .
C6B C -0.0840(6) 0.12455(10) 0.5390(4) 0.0217(6) Uani 1 1 d . . .
H6B H -0.1944 0.1489 0.5629 0.026 Uiso 1 1 calc R . .
C7B C -0.0997(6) 0.10504(11) 0.3723(4) 0.0248(6) Uani 1 1 d . . .
H7B H -0.2185 0.1158 0.2835 0.030 Uiso 1 1 calc R . .
C8B C 0.0612(6) 0.06956(10) 0.3378(4) 0.0204(6) Uani 1 1 d . . .
H8B H 0.0524 0.0560 0.2238 0.024 Uiso 1 1 calc R . .
C9B C 0.2359(5) 0.05340(9) 0.4671(4) 0.0188(5) Uani 1 1 d . . .
H9B H 0.3457 0.0291 0.4418 0.023 Uiso 1 1 calc R . .
C10B C 0.1085(6) 0.13235(9) 0.8509(4) 0.0189(5) Uani 1 1 d . . .
H13B H 0.0893 0.1105 0.9470 0.023 Uiso 1 1 calc R . .
H14B H -0.0423 0.1529 0.8619 0.023 Uiso 1 1 calc R . .
C11B C 0.3696(6) 0.15712(10) 0.8808(4) 0.0238(6) Uani 1 1 d . . .
H15B H 0.5214 0.1366 0.8743 0.029 Uiso 1 1 calc R . .
H16B H 0.3920 0.1788 0.7843 0.029 Uiso 1 1 calc R . .
C12B C 0.3747(8) 0.17999(12) 1.0610(5) 0.0336(8) Uani 1 1 d . . .
H17B H 0.5446 0.1954 1.0751 0.050 Uiso 1 1 calc R . .
H18B H 0.3557 0.1586 1.1570 0.050 Uiso 1 1 calc R . .
H19B H 0.2270 0.2008 1.0670 0.050 Uiso 1 1 calc R . .
O1B O 0.3790(4) -0.01950(7) 1.0457(3) 0.0223(4) Uani 1 1 d . . .
O2B O 0.9117(4) -0.02061(7) 0.8650(3) 0.0177(4) Uani 1 1 d . . .
O3B O 0.4091(4) 0.05957(6) 0.7712(3) 0.0180(4) Uani 1 1 d . . .
H1B H 0.423(19) -0.035(3) 1.138(13) 0.14(3) Uiso 1 1 d . . .
H2B H 1.070(8) -0.0191(12) 0.914(5) 0.019(8) Uiso 1 1 d . . .


_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
C1A O1A 1.432(3) . ?
C1A C2A 1.532(4) . ?
C1A H11A 0.9900 . ?
C1A H12A 0.9900 . ?
C2A O2A 1.424(3) . ?
C2A C3A 1.533(3) . ?
C2A H20A 1.0000 . ?
C3A O3A 1.432(3) . ?
C3A H31A 0.9900 . ?
C3A H32A 0.9900 . ?
C4A O3A 1.376(3) . ?
C4A C9A 1.392(4) . ?
C4A C5A 1.405(4) . ?
C5A C6A 1.374(4) . ?
C5A C10A 1.524(4) . ?
C6A C7A 1.421(5) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.370(5) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.393(4) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.523(5) . ?
C10A H13A 0.9900 . ?
C10A H14A 0.9900 . ?
C11A C12A 1.530(5) . ?
C11A H15A 0.9900 . ?
C11A H16A 0.9900 . ?
C12A H17A 0.9800 . ?
C12A H18A 0.9800 . ?
C12A H19A 0.9800 . ?
O1A H1A 0.87(4) . ?
O2A H2A 0.89(6) . ?
C1B O1B 1.427(3) . ?
C1B C2B 1.519(4) . ?
C1B H11B 0.9900 . ?
C1B H12B 0.9900 . ?
C2B O2B 1.436(3) . ?
C2B C3B 1.514(4) . ?
C2B H20B 1.0000 . ?
C3B O3B 1.431(3) . ?
C3B H31B 0.9900 . ?
C3B H32B 0.9900 . ?
C4B O3B 1.372(3) . ?
C4B C9B 1.397(4) . ?
C4B C5B 1.405(4) . ?
C5B C6B 1.395(4) . ?
C5B C10B 1.503(4) . ?
C6B C7B 1.385(5) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.385(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.394(4) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.531(4) . ?
C10B H13B 0.9900 . ?
C10B H14B 0.9900 . ?
C11B C12B 1.520(5) . ?
C11B H15B 0.9900 . ?
C11B H16B 0.9900 . ?
C12B H17B 0.9800 . ?
C12B H18B 0.9800 . ?
C12B H19B 0.9800 . ?
O1B H1B 0.87(10) . ?
O2B H2B 0.87(4) . ?

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
O1A C1A C2A 110.7(2) . . ?
O1A C1A H11A 109.5 . . ?
C2A C1A H11A 109.5 . . ?
O1A C1A H12A 109.5 . . ?
C2A C1A H12A 109.5 . . ?
H11A C1A H12A 108.1 . . ?
O2A C2A C1A 112.5(2) . . ?
O2A C2A C3A 105.8(2) . . ?
C1A C2A C3A 112.7(2) . . ?
O2A C2A H20A 108.6 . . ?
C1A C2A H20A 108.6 . . ?
C3A C2A H20A 108.6 . . ?
O3A C3A C2A 106.3(2) . . ?
O3A C3A H31A 110.5 . . ?
C2A C3A H31A 110.5 . . ?
O3A C3A H32A 110.5 . . ?
C2A C3A H32A 110.5 . . ?
H31A C3A H32A 108.7 . . ?
O3A C4A C9A 123.2(2) . . ?
O3A C4A C5A 115.8(2) . . ?
C9A C4A C5A 121.0(3) . . ?
C6A C5A C4A 118.8(3) . . ?
C6A C5A C10A 121.3(3) . . ?
C4A C5A C10A 119.9(3) . . ?
C5A C6A C7A 120.9(3) . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A H6A 119.5 . . ?
C8A C7A C6A 118.9(3) . . ?
C8A C7A H7A 120.6 . . ?
C6A C7A H7A 120.6 . . ?
C7A C8A C9A 121.5(3) . . ?
C7A C8A H8A 119.2 . . ?
C9A C8A H8A 119.2 . . ?
C4A C9A C8A 118.9(3) . . ?
C4A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
C11A C10A C5A 113.0(2) . . ?
C11A C10A H13A 109.0 . . ?
C5A C10A H13A 109.0 . . ?
C11A C10A H14A 109.0 . . ?
C5A C10A H14A 109.0 . . ?
H13A C10A H14A 107.8 . . ?
C10A C11A C12A 112.2(3) . . ?
C10A C11A H15A 109.2 . . ?
C12A C11A H15A 109.2 . . ?
C10A C11A H16A 109.2 . . ?
C12A C11A H16A 109.2 . . ?
H15A C11A H16A 107.9 . . ?
C11A C12A H17A 109.5 . . ?
C11A C12A H18A 109.5 . . ?
H17A C12A H18A 109.5 . . ?
C11A C12A H19A 109.5 . . ?
H17A C12A H19A 109.5 . . ?
H18A C12A H19A 109.5 . . ?
C1A O1A H1A 103(2) . . ?
C2A O2A H2A 105(4) . . ?
C4A O3A C3A 116.5(2) . . ?
O1B C1B C2B 111.6(2) . . ?
O1B C1B H11B 109.3 . . ?
C2B C1B H11B 109.3 . . ?
O1B C1B H12B 109.3 . . ?
C2B C1B H12B 109.3 . . ?
H11B C1B H12B 108.0 . . ?
O2B C2B C3B 105.5(2) . . ?
O2B C2B C1B 112.2(2) . . ?
C3B C2B C1B 112.4(2) . . ?
O2B C2B H20B 108.9 . . ?
C3B C2B H20B 108.9 . . ?
C1B C2B H20B 108.9 . . ?
O3B C3B C2B 107.1(2) . . ?
O3B C3B H31B 110.3 . . ?
C2B C3B H31B 110.3 . . ?
O3B C3B H32B 110.3 . . ?
C2B C3B H32B 110.3 . . ?
H31B C3B H32B 108.5 . . ?
O3B C4B C9B 123.3(2) . . ?
O3B C4B C5B 115.7(2) . . ?
C9B C4B C5B 121.1(2) . . ?
C6B C5B C4B 117.6(3) . . ?
C6B C5B C10B 121.6(3) . . ?
C4B C5B C10B 120.8(2) . . ?
C7B C6B C5B 122.5(3) . . ?
C7B C6B H6B 118.8 . . ?
C5B C6B H6B 118.8 . . ?
C8B C7B C6B 118.7(3) . . ?
C8B C7B H7B 120.7 . . ?
C6B C7B H7B 120.7 . . ?
C7B C8B C9B 121.3(3) . . ?
C7B C8B H8B 119.4 . . ?
C9B C8B H8B 119.4 . . ?
C8B C9B C4B 119.0(3) . . ?
C8B C9B H9B 120.5 . . ?
C4B C9B H9B 120.5 . . ?
C5B C10B C11B 114.7(2) . . ?
C5B C10B H13B 108.6 . . ?
C11B C10B H13B 108.6 . . ?
C5B C10B H14B 108.6 . . ?
C11B C10B H14B 108.6 . . ?
H13B C10B H14B 107.6 . . ?
C12B C11B C10B 112.0(3) . . ?
C12B C11B H15B 109.2 . . ?
C10B C11B H15B 109.2 . . ?
C12B C11B H16B 109.2 . . ?
C10B C11B H16B 109.2 . . ?
H15B C11B H16B 107.9 . . ?
C11B C12B H17B 109.5 . . ?
C11B C12B H18B 109.5 . . ?
H17B C12B H18B 109.5 . . ?
C11B C12B H19B 109.5 . . ?
H17B C12B H19B 109.5 . . ?
H18B C12B H19B 109.5 . . ?
C1B O1B H1B 96(6) . . ?
C2B O2B H2B 113(2) . . ?
C4B O3B C3B 117.6(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
O1A C1A C2A O2A -69.1(3) . . . . ?
O1A C1A C2A C3A 50.4(3) . . . . ?
O2A C2A C3A O3A 176.4(2) . . . . ?
C1A C2A C3A O3A 53.1(3) . . . . ?
O3A C4A C5A C6A -179.4(3) . . . . ?
C9A C4A C5A C6A -0.1(4) . . . . ?
O3A C4A C5A C10A 1.3(4) . . . . ?
C9A C4A C5A C10A -179.5(3) . . . . ?
C4A C5A C6A C7A -0.8(4) . . . . ?
C10A C5A C6A C7A 178.5(3) . . . . ?
C5A C6A C7A C8A 1.0(5) . . . . ?
C6A C7A C8A C9A -0.2(5) . . . . ?
O3A C4A C9A C8A -180.0(3) . . . . ?
C5A C4A C9A C8A 0.9(4) . . . . ?
C7A C8A C9A C4A -0.7(5) . . . . ?
C6A C5A C10A C11A -93.5(3) . . . . ?
C4A C5A C10A C11A 85.8(3) . . . . ?
C5A C10A C11A C12A -173.5(3) . . . . ?
C9A C4A O3A C3A 0.6(4) . . . . ?
C5A C4A O3A C3A 179.7(2) . . . . ?
C2A C3A O3A C4A 177.4(2) . . . . ?
O1B C1B C2B O2B -69.0(3) . . . . ?
O1B C1B C2B C3B 49.6(3) . . . . ?
O2B C2B C3B O3B 176.7(2) . . . . ?
C1B C2B C3B O3B 54.2(3) . . . . ?
O3B C4B C5B C6B -178.7(2) . . . . ?
C9B C4B C5B C6B 0.9(4) . . . . ?
O3B C4B C5B C10B 2.8(4) . . . . ?
C9B C4B C5B C10B -177.6(3) . . . . ?
C4B C5B C6B C7B -0.5(4) . . . . ?
C10B C5B C6B C7B 177.9(3) . . . . ?
C5B C6B C7B C8B 0.0(5) . . . . ?
C6B C7B C8B C9B 0.2(4) . . . . ?
C7B C8B C9B C4B 0.2(4) . . . . ?
O3B C4B C9B C8B 178.9(3) . . . . ?
C5B C4B C9B C8B -0.7(4) . . . . ?
C6B C5B C10B C11B -108.7(3) . . . . ?
C4B C5B C10B C11B 69.7(3) . . . . ?
C5B C10B C11B C12B 178.6(3) . . . . ?
C9B C4B O3B C3B 2.7(4) . . . . ?
C5B C4B O3B C3B -177.7(2) . . . . ?
C2B C3B O3B C4B 175.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 983814'
#######################################################################
#
#                 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_bredikh_sm46hex

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26

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           Trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_symmetry_Int_Tables_number      145

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   14.756(10)
_cell_length_b                   14.756(10)
_cell_length_c                   4.819(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     908.7(11)
_cell_formula_units_Z            3
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4657
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      26.31

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             342
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12474
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_av_sigmaI/netI    0.1235
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.99
_reflns_number_total             2933
_reflns_number_gt                2431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;
_chemical_absolute_configuration rm
_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)+(0.0620P)²+0.0337P] 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         2933
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.10061(16) 0.86080(14) 0.4485(4) 0.0391(4) Uani 1 1 d . . .
H11 H 0.0482 0.8063 0.3244 0.047 Uiso 1 1 calc R . .
H12 H 0.1412 0.8319 0.5371 0.047 Uiso 1 1 calc R . .
C2 C 0.17364(14) 0.95512(15) 0.2773(3) 0.0340(4) Uani 1 1 d . . .
H20 H 0.2107 0.9343 0.1398 0.041 Uiso 1 1 calc R . .
C3 C 0.25404(14) 1.04418(14) 0.4533(4) 0.0338(4) Uani 1 1 d . . .
H31 H 0.2999 1.1051 0.3354 0.041 Uiso 1 1 calc R . .
H32 H 0.2190 1.0661 0.5912 0.041 Uiso 1 1 calc R . .
C4 C 0.39069(13) 1.07168(17) 0.7703(4) 0.0402(4) Uani 1 1 d . . .
C5 C 0.44815(15) 1.0307(2) 0.8943(4) 0.0478(5) Uani 1 1 d . . .
C6 C 0.52308(17) 1.0941(3) 1.0907(5) 0.0622(7) Uani 1 1 d . . .
H6 H 0.5623 1.0680 1.1825 0.075 Uiso 1 1 calc R . .
C7 C 0.54203(17) 1.1929(2) 1.1556(5) 0.0612(7) Uani 1 1 d . . .
H7 H 0.5927 1.2331 1.2924 0.073 Uiso 1 1 calc R . .
C8 C 0.48808(17) 1.2330(2) 1.0238(4) 0.0545(6) Uani 1 1 d . . .
H8 H 0.5027 1.3021 1.0642 0.065 Uiso 1 1 calc R . .
C9 C 0.41106(15) 1.17223(16) 0.8288(4) 0.0459(5) Uani 1 1 d . . .
H9 H 0.3730 1.1997 0.7370 0.055 Uiso 1 1 calc R . .
C10 C 0.4288(2) 0.9239(2) 0.8080(5) 0.0605(7) Uani 1 1 d . . .
H13 H 0.4086 0.9153 0.6076 0.073 Uiso 1 1 calc R . .
C11 C 0.3395(3) 0.8377(2) 0.9597(8) 0.0802(9) Uani 1 1 d . . .
H16 H 0.3577 0.8403 1.1563 0.120 Uiso 1 1 calc R . .
H15 H 0.3243 0.7703 0.8809 0.120 Uiso 1 1 calc R . .
H14 H 0.2778 0.8457 0.9418 0.120 Uiso 1 1 calc R . .
C12 C 0.5279(3) 0.9157(4) 0.8276(12) 0.1115(14) Uani 1 1 d . . .
H18 H 0.5493 0.9212 1.0222 0.167 Uiso 1 1 calc R . .
H17 H 0.5841 0.9725 0.7206 0.167 Uiso 1 1 calc R . .
H19 H 0.5139 0.8482 0.7524 0.167 Uiso 1 1 calc R . .
O1 O 0.04782(10) 0.88452(11) 0.6572(3) 0.0426(3) Uani 1 1 d . . .
O2 O 0.11737(11) 0.99528(11) 0.1326(3) 0.0403(3) Uani 1 1 d . . .
O3 O 0.31374(10) 1.00553(11) 0.5897(3) 0.0403(3) Uani 1 1 d . . .
H1 H -0.007(2) 0.8864(19) 0.587(5) 0.047(6) Uiso 1 1 d . . .
H2 H 0.099(2) 0.961(2) -0.009(7) 0.063(8) Uiso 1 1 d . . .


_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 1.419(3) . ?
C1 C2 1.510(3) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 O2 1.421(2) . ?
C2 C3 1.515(3) . ?
C2 H20 1.0000 . ?
C3 O3 1.427(2) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O3 1.375(2) . ?
C4 C9 1.388(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.400(3) . ?
C5 C10 1.512(4) . ?
C6 C7 1.376(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.487(5) . ?
C10 C12 1.529(4) . ?
C10 H13 1.0000 . ?
C11 H16 0.9800 . ?
C11 H15 0.9800 . ?
C11 H14 0.9800 . ?
C12 H18 0.9800 . ?
C12 H17 0.9800 . ?
C12 H19 0.9800 . ?
O1 H1 0.88(3) . ?
O2 H2 0.81(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
O1 C1 C2 112.75(15) . . ?
O1 C1 H11 109.0 . . ?
C2 C1 H11 109.0 . . ?
O1 C1 H12 109.0 . . ?
C2 C1 H12 109.0 . . ?
H11 C1 H12 107.8 . . ?
O2 C2 C1 110.86(15) . . ?
O2 C2 C3 106.29(14) . . ?
C1 C2 C3 112.48(15) . . ?
O2 C2 H20 109.0 . . ?
C1 C2 H20 109.0 . . ?
C3 C2 H20 109.0 . . ?
O3 C3 C2 106.47(14) . . ?
O3 C3 H31 110.4 . . ?
C2 C3 H31 110.4 . . ?
O3 C3 H32 110.4 . . ?
C2 C3 H32 110.4 . . ?
H31 C3 H32 108.6 . . ?
O3 C4 C9 123.24(18) . . ?
O3 C4 C5 115.30(18) . . ?
C9 C4 C5 121.46(18) . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 C10 119.63(18) . . ?
C6 C5 C10 123.8(2) . . ?
C7 C6 C5 122.4(2) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 119.6(2) . . ?
C4 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C5 112.37(19) . . ?
C11 C10 C12 112.1(3) . . ?
C5 C10 C12 112.1(3) . . ?
C11 C10 H13 106.6 . . ?
C5 C10 H13 106.6 . . ?
C12 C10 H13 106.6 . . ?
C10 C11 H16 109.5 . . ?
C10 C11 H15 109.5 . . ?
H16 C11 H15 109.5 . . ?
C10 C11 H14 109.5 . . ?
H16 C11 H14 109.5 . . ?
H15 C11 H14 109.5 . . ?
C10 C12 H18 109.5 . . ?
C10 C12 H17 109.5 . . ?
H18 C12 H17 109.5 . . ?
C10 C12 H19 109.5 . . ?
H18 C12 H19 109.5 . . ?
H17 C12 H19 109.5 . . ?
C1 O1 H1 110.9(16) . . ?
C2 O2 H2 104(2) . . ?
C4 O3 C3 117.61(15) . . ?

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 -62.35(19) . . . . ?
O1 C1 C2 C3 56.51(19) . . . . ?
O2 C2 C3 O3 -177.51(14) . . . . ?
C1 C2 C3 O3 60.99(18) . . . . ?
O3 C4 C5 C6 -176.57(18) . . . . ?
C9 C4 C5 C6 3.3(3) . . . . ?
O3 C4 C5 C10 4.8(3) . . . . ?
C9 C4 C5 C10 -175.3(2) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C10 C5 C6 C7 177.0(2) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
O3 C4 C9 C8 177.44(17) . . . . ?
C5 C4 C9 C8 -2.4(3) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C4 C5 C10 C11 -84.4(3) . . . . ?
C6 C5 C10 C11 97.0(3) . . . . ?
C4 C5 C10 C12 148.3(3) . . . . ?
C6 C5 C10 C12 -30.3(4) . . . . ?
C9 C4 O3 C3 1.3(2) . . . . ?
C5 C4 O3 C3 -178.84(16) . . . . ?
C2 C3 O3 C4 -178.06(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 983815'
#######################################################################
#
#                 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_bred_sm47fin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26

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           Orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_Int_Tables_number      18

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

_cell_length_a                   16.149(2)
_cell_length_b                   17.459(2)
_cell_length_c                   8.1259(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2291.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7710
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9847
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32606
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.98
_reflns_number_total             5470
_reflns_number_gt                4134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_chemical_absolute_configuration rm
_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)+(0.0550P)²+0.3177P] 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         5470
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
C1B C 0.46863(11) 0.13733(10) 0.3561(3) 0.0332(4) Uani 1 1 d . . .
H11B H 0.4521 0.1555 0.4667 0.040 Uiso 1 1 calc R . .
H12B H 0.4576 0.1791 0.2766 0.040 Uiso 1 1 calc R . .
C2B C 0.56043(11) 0.11962(10) 0.3564(2) 0.0310(4) Uani 1 1 d . . .
H20B H 0.5771 0.1001 0.2456 0.037 Uiso 1 1 calc R . .
C3B C 0.61242(12) 0.18855(10) 0.3993(2) 0.0344(4) Uani 1 1 d . . .
H31B H 0.5958 0.2090 0.5080 0.041 Uiso 1 1 calc R . .
H32B H 0.6716 0.1740 0.4045 0.041 Uiso 1 1 calc R . .
C4B C 0.64424(11) 0.31221(10) 0.2898(2) 0.0337(4) Uani 1 1 d . . .
C5B C 0.6495(4) 0.3576(5) 0.1595(12) 0.0288(14) Uani 0.482(5) 1 d P A 1
C6B C 0.6883(8) 0.4263(7) 0.169(2) 0.0365(15) Uani 0.482(5) 1 d P A 1
H6B H 0.6865 0.4614 0.0794 0.044 Uiso 0.482(5) 1 calc PR A 1
C7B C 0.7334(15) 0.4453(13) 0.321(3) 0.0322(19) Uani 0.482(5) 1 d P A 1
H7B H 0.7645 0.4914 0.3265 0.039 Uiso 0.482(5) 1 calc PR A 1
C8B C 0.7314(18) 0.4012(19) 0.444(3) 0.038(2) Uani 0.482(5) 1 d P A 1
H8B H 0.7593 0.4154 0.5426 0.045 Uiso 0.482(5) 1 calc PR A 1
C9B C 0.6877(15) 0.3301(17) 0.437(3) 0.0300(19) Uani 0.482(5) 1 d P A 1
H9B H 0.6877 0.2958 0.5280 0.036 Uiso 0.482(5) 1 calc PR A 1
C10B C 0.6077(3) 0.3327(3) -0.0011(6) 0.0338(11) Uani 0.482(5) 1 d P A 1
H13B H 0.6180 0.2765 -0.0129 0.041 Uiso 0.482(5) 1 calc PR A 1
C11B C 0.6422(3) 0.3703(3) -0.1540(6) 0.0517(14) Uani 0.482(5) 1 d P A 1
H14B H 0.7022 0.3624 -0.1584 0.078 Uiso 0.482(5) 1 calc PR A 1
H15B H 0.6303 0.4253 -0.1511 0.078 Uiso 0.482(5) 1 calc PR A 1
H16B H 0.6164 0.3476 -0.2517 0.078 Uiso 0.482(5) 1 calc PR A 1
C12B C 0.5146(3) 0.3430(3) 0.0098(6) 0.0437(13) Uani 0.482(5) 1 d P A 1
H17B H 0.4939 0.3176 0.1092 0.066 Uiso 0.482(5) 1 calc PR A 1
H18B H 0.4884 0.3202 -0.0873 0.066 Uiso 0.482(5) 1 calc PR A 1
H19B H 0.5014 0.3977 0.0145 0.066 Uiso 0.482(5) 1 calc PR A 1
C5C C 0.6217(4) 0.3700(5) 0.1629(12) 0.0322(14) Uani 0.518(5) 1 d P A 2
C6C C 0.6674(8) 0.4405(7) 0.1776(19) 0.0365(15) Uani 0.518(5) 1 d P A 2
H6C H 0.6569 0.4792 0.0981 0.044 Uiso 0.518(5) 1 calc PR A 2
C7C C 0.7219(13) 0.4555(12) 0.291(3) 0.0322(19) Uani 0.518(5) 1 d P A 2
H7C H 0.7490 0.5038 0.2952 0.039 Uiso 0.518(5) 1 calc PR A 2
C8C C 0.7405(17) 0.3955(18) 0.414(3) 0.038(2) Uani 0.518(5) 1 d P A 2
H8C H 0.7810 0.4045 0.4963 0.045 Uiso 0.518(5) 1 calc PR A 2
C9C C 0.7001(13) 0.3282(16) 0.409(3) 0.0300(19) Uani 0.518(5) 1 d P A 2
H9C H 0.7111 0.2909 0.4911 0.036 Uiso 0.518(5) 1 calc PR A 2
C10C C 0.5598(4) 0.3565(3) 0.0257(6) 0.0391(11) Uani 0.518(5) 1 d P A 2
H13C H 0.5234 0.3128 0.0595 0.047 Uiso 0.518(5) 1 calc PR A 2
C11C C 0.6044(4) 0.3332(3) -0.1314(6) 0.0549(14) Uani 0.518(5) 1 d P A 2
H14C H 0.6399 0.2889 -0.1091 0.082 Uiso 0.518(5) 1 calc PR A 2
H15C H 0.6384 0.3760 -0.1704 0.082 Uiso 0.518(5) 1 calc PR A 2
H16C H 0.5636 0.3197 -0.2158 0.082 Uiso 0.518(5) 1 calc PR A 2
C12C C 0.5043(3) 0.4257(3) -0.0052(6) 0.0538(13) Uani 0.518(5) 1 d P A 2
H17C H 0.4765 0.4402 0.0974 0.081 Uiso 0.518(5) 1 calc PR A 2
H18C H 0.4627 0.4127 -0.0885 0.081 Uiso 0.518(5) 1 calc PR A 2
H19C H 0.5380 0.4686 -0.0443 0.081 Uiso 0.518(5) 1 calc PR A 2
C1A C 1.01845(11) 0.36221(10) 0.1469(2) 0.0325(4) Uani 1 1 d . . .
H11A H 1.0251 0.3203 0.2279 0.039 Uiso 1 1 calc R . .
H12A H 1.0345 0.3421 0.0375 0.039 Uiso 1 1 calc R . .
C2A C 0.92828(11) 0.38685(10) 0.1423(2) 0.0317(4) Uani 1 1 d . . .
H20A H 0.9122 0.4078 0.2523 0.038 Uiso 1 1 calc R . .
C3A C 0.87130(12) 0.32160(10) 0.0980(2) 0.0338(4) Uani 1 1 d . . .
H31A H 0.8134 0.3399 0.0900 0.041 Uiso 1 1 calc R . .
H32A H 0.8874 0.2993 -0.0093 0.041 Uiso 1 1 calc R . .
C4A C 0.83550(10) 0.19864(9) 0.2048(2) 0.0307(4) Uani 1 1 d . . .
C5A C 0.84806(11) 0.14330(10) 0.3257(2) 0.0314(4) Uani 1 1 d . . .
C6A C 0.80632(11) 0.07422(11) 0.3075(3) 0.0388(5) Uani 1 1 d . . .
H6A H 0.8140 0.0354 0.3880 0.047 Uiso 1 1 calc R . .
C7A C 0.75398(11) 0.06014(11) 0.1761(3) 0.0407(5) Uani 1 1 d . . .
H7A H 0.7259 0.0125 0.1675 0.049 Uiso 1 1 calc R . .
C8A C 0.74298(11) 0.11547(11) 0.0583(3) 0.0384(5) Uani 1 1 d . . .
H8A H 0.7076 0.1060 -0.0328 0.046 Uiso 1 1 calc R . .
C9A C 0.78308(11) 0.18482(11) 0.0718(2) 0.0361(4) Uani 1 1 d . . .
H9A H 0.7750 0.2232 -0.0095 0.043 Uiso 1 1 calc R . .
C11A C 0.85177(15) 0.17981(14) 0.6235(3) 0.0546(6) Uani 1 1 d . . .
H17A H 0.8214 0.2273 0.6009 0.082 Uiso 1 1 calc R . .
H18A H 0.8884 0.1875 0.7182 0.082 Uiso 1 1 calc R . .
H19A H 0.8124 0.1386 0.6480 0.082 Uiso 1 1 calc R . .
C12A C 0.95917(14) 0.08958(13) 0.5113(3) 0.0520(6) Uani 1 1 d . . .
H14A H 0.9253 0.0471 0.5522 0.078 Uiso 1 1 calc R . .
H15A H 0.9998 0.1042 0.5953 0.078 Uiso 1 1 calc R . .
H16A H 0.9882 0.0736 0.4111 0.078 Uiso 1 1 calc R . .
O1B O 0.41992(8) 0.07223(7) 0.31321(17) 0.0338(3) Uani 1 1 d . . .
O2B O 0.57875(9) 0.06313(7) 0.47757(17) 0.0347(3) Uani 1 1 d . . .
O3B O 0.59996(8) 0.24513(7) 0.27495(18) 0.0379(3) Uani 1 1 d . A .
O1A O 1.07189(8) 0.42361(7) 0.18980(18) 0.0326(3) Uani 1 1 d . . .
O2A O 0.91625(9) 0.44425(7) 0.01956(16) 0.0345(3) Uani 1 1 d . . .
O3A O 0.87875(8) 0.26577(6) 0.22536(17) 0.0343(3) Uani 1 1 d . . .
C10A C 0.90345(12) 0.15801(11) 0.4728(3) 0.0398(5) Uani 1 1 d . . .
H13A H 0.9400 0.2025 0.4456 0.048 Uiso 1 1 calc R . .
H1A H 1.0715(12) 0.4273(12) 0.291(3) 0.037(6) Uiso 1 1 d . . .
H2B H 0.5788(18) 0.0182(16) 0.425(3) 0.076(9) Uiso 1 1 d . . .
H1B H 0.4241(17) 0.0653(16) 0.204(4) 0.077(9) Uiso 1 1 d . . .
H2A H 0.9262(15) 0.4889(13) 0.071(3) 0.055(7) Uiso 1 1 d . . .


_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
C1B O1B 1.426(2) . ?
C1B C2B 1.514(2) . ?
C1B H11B 0.9900 . ?
C1B H12B 0.9900 . ?
C2B O2B 1.425(2) . ?
C2B C3B 1.508(2) . ?
C2B H20B 1.0000 . ?
C3B O3B 1.427(2) . ?
C3B H31B 0.9900 . ?
C3B H32B 0.9900 . ?
C4B C5B 1.325(10) . ?
C4B C9C 1.35(3) . ?
C4B O3B 1.378(2) . ?
C4B C9B 1.42(3) . ?
C4B C5C 1.487(8) . ?
C5B C6B 1.356(18) . ?
C5B C10B 1.532(11) . ?
C6B C7B 1.47(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.26(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.43(4) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.511(6) . ?
C10B C12B 1.517(6) . ?
C10B H13B 1.0000 . ?
C11B H14B 0.9800 . ?
C11B H15B 0.9800 . ?
C11B H16B 0.9800 . ?
C12B H17B 0.9800 . ?
C12B H18B 0.9800 . ?
C12B H19B 0.9800 . ?
C5C C6C 1.441(17) . ?
C5C C10C 1.516(10) . ?
C6C C7C 1.30(3) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.48(4) . ?
C7C H7C 0.9500 . ?
C8C C9C 1.34(4) . ?
C8C H8C 0.9500 . ?
C9C H9C 0.9500 . ?
C10C C11C 1.522(7) . ?
C10C C12C 1.525(7) . ?
C10C H13C 1.0000 . ?
C11C H14C 0.9800 . ?
C11C H15C 0.9800 . ?
C11C H16C 0.9800 . ?
C12C H17C 0.9800 . ?
C12C H18C 0.9800 . ?
C12C H19C 0.9800 . ?
C1A O1A 1.420(2) . ?
C1A C2A 1.519(3) . ?
C1A H11A 0.9900 . ?
C1A H12A 0.9900 . ?
C2A O2A 1.427(2) . ?
C2A C3A 1.508(2) . ?
C2A H20A 1.0000 . ?
C3A O3A 1.427(2) . ?
C3A H31A 0.9900 . ?
C3A H32A 0.9900 . ?
C4A O3A 1.375(2) . ?
C4A C5A 1.393(3) . ?
C4A C9A 1.394(3) . ?
C5A C6A 1.389(2) . ?
C5A C10A 1.515(3) . ?
C6A C7A 1.384(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.371(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.377(3) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C11A C10A 1.530(3) . ?
C11A H17A 0.9800 . ?
C11A H18A 0.9800 . ?
C11A H19A 0.9800 . ?
C12A C10A 1.528(3) . ?
C12A H14A 0.9800 . ?
C12A H15A 0.9800 . ?
C12A H16A 0.9800 . ?
O1B H1B 0.90(3) . ?
O2B H2B 0.89(3) . ?
O1A H1A 0.82(2) . ?
O2A H2A 0.90(2) . ?
C10A H13A 1.0000 . ?

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
O1B C1B C2B 112.20(14) . . ?
O1B C1B H11B 109.2 . . ?
C2B C1B H11B 109.2 . . ?
O1B C1B H12B 109.2 . . ?
C2B C1B H12B 109.2 . . ?
H11B C1B H12B 107.9 . . ?
O2B C2B C3B 106.10(15) . . ?
O2B C2B C1B 110.25(15) . . ?
C3B C2B C1B 112.49(15) . . ?
O2B C2B H20B 109.3 . . ?
C3B C2B H20B 109.3 . . ?
C1B C2B H20B 109.3 . . ?
O3B C3B C2B 108.08(15) . . ?
O3B C3B H31B 110.1 . . ?
C2B C3B H31B 110.1 . . ?
O3B C3B H32B 110.1 . . ?
C2B C3B H32B 110.1 . . ?
H31B C3B H32B 108.4 . . ?
C5B C4B C9C 113.9(11) . . ?
C5B C4B O3B 118.2(4) . . ?
C9C C4B O3B 125.8(12) . . ?
C5B C4B C9B 120.6(12) . . ?
O3B C4B C9B 121.1(12) . . ?
C9C C4B C5C 121.3(12) . . ?
O3B C4B C5C 112.9(4) . . ?
C9B C4B C5C 123.7(13) . . ?
C4B C5B C6B 120.9(10) . . ?
C4B C5B C10B 118.9(7) . . ?
C6B C5B C10B 120.1(10) . . ?
C5B C6B C7B 118.3(15) . . ?
C5B C6B H6B 120.8 . . ?
C7B C6B H6B 120.8 . . ?
C8B C7B C6B 121(3) . . ?
C8B C7B H7B 119.5 . . ?
C6B C7B H7B 119.5 . . ?
C7B C8B C9B 121(3) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B H8B 119.7 . . ?
C4B C9B C8B 118(2) . . ?
C4B C9B H9B 121.0 . . ?
C8B C9B H9B 121.0 . . ?
C11B C10B C12B 111.2(4) . . ?
C11B C10B C5B 114.5(5) . . ?
C12B C10B C5B 110.7(4) . . ?
C11B C10B H13B 106.6 . . ?
C12B C10B H13B 106.6 . . ?
C5B C10B H13B 106.6 . . ?
C10B C11B H14B 109.5 . . ?
C10B C11B H15B 109.5 . . ?
H14B C11B H15B 109.5 . . ?
C10B C11B H16B 109.5 . . ?
H14B C11B H16B 109.5 . . ?
H15B C11B H16B 109.5 . . ?
C10B C12B H17B 109.5 . . ?
C10B C12B H18B 109.5 . . ?
H17B C12B H18B 109.5 . . ?
C10B C12B H19B 109.5 . . ?
H17B C12B H19B 109.5 . . ?
H18B C12B H19B 109.5 . . ?
C6C C5C C4B 113.4(8) . . ?
C6C C5C C10C 122.1(8) . . ?
C4B C5C C10C 124.5(6) . . ?
C7C C6C C5C 125.2(14) . . ?
C7C C6C H6C 117.4 . . ?
C5C C6C H6C 117.4 . . ?
C6C C7C C8C 118(2) . . ?
C6C C7C H7C 120.9 . . ?
C8C C7C H7C 120.9 . . ?
C9C C8C C7C 120(3) . . ?
C9C C8C H8C 120.0 . . ?
C7C C8C H8C 120.0 . . ?
C8C C9C C4B 122(2) . . ?
C8C C9C H9C 119.1 . . ?
C4B C9C H9C 119.1 . . ?
C5C C10C C11C 110.3(5) . . ?
C5C C10C C12C 112.7(4) . . ?
C11C C10C C12C 110.6(4) . . ?
C5C C10C H13C 107.7 . . ?
C11C C10C H13C 107.7 . . ?
C12C C10C H13C 107.7 . . ?
C10C C11C H14C 109.5 . . ?
C10C C11C H15C 109.5 . . ?
H14C C11C H15C 109.5 . . ?
C10C C11C H16C 109.5 . . ?
H14C C11C H16C 109.5 . . ?
H15C C11C H16C 109.5 . . ?
C10C C12C H17C 109.5 . . ?
C10C C12C H18C 109.5 . . ?
H17C C12C H18C 109.5 . . ?
C10C C12C H19C 109.5 . . ?
H17C C12C H19C 109.5 . . ?
H18C C12C H19C 109.5 . . ?
O1A C1A C2A 112.02(14) . . ?
O1A C1A H11A 109.2 . . ?
C2A C1A H11A 109.2 . . ?
O1A C1A H12A 109.2 . . ?
C2A C1A H12A 109.2 . . ?
H11A C1A H12A 107.9 . . ?
O2A C2A C3A 106.27(15) . . ?
O2A C2A C1A 110.27(15) . . ?
C3A C2A C1A 112.14(15) . . ?
O2A C2A H20A 109.4 . . ?
C3A C2A H20A 109.4 . . ?
C1A C2A H20A 109.4 . . ?
O3A C3A C2A 106.92(14) . . ?
O3A C3A H31A 110.3 . . ?
C2A C3A H31A 110.3 . . ?
O3A C3A H32A 110.3 . . ?
C2A C3A H32A 110.3 . . ?
H31A C3A H32A 108.6 . . ?
O3A C4A C5A 115.57(16) . . ?
O3A C4A C9A 123.41(17) . . ?
C5A C4A C9A 121.02(16) . . ?
C6A C5A C4A 117.16(17) . . ?
C6A C5A C10A 121.16(17) . . ?
C4A C5A C10A 121.67(16) . . ?
C7A C6A C5A 122.17(19) . . ?
C7A C6A H6A 118.9 . . ?
C5A C6A H6A 118.9 . . ?
C8A C7A C6A 119.49(17) . . ?
C8A C7A H7A 120.3 . . ?
C6A C7A H7A 120.3 . . ?
C7A C8A C9A 120.21(19) . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A H8A 119.9 . . ?
C8A C9A C4A 119.95(19) . . ?
C8A C9A H9A 120.0 . . ?
C4A C9A H9A 120.0 . . ?
C10A C11A H17A 109.5 . . ?
C10A C11A H18A 109.5 . . ?
H17A C11A H18A 109.5 . . ?
C10A C11A H19A 109.5 . . ?
H17A C11A H19A 109.5 . . ?
H18A C11A H19A 109.5 . . ?
C10A C12A H14A 109.5 . . ?
C10A C12A H15A 109.5 . . ?
H14A C12A H15A 109.5 . . ?
C10A C12A H16A 109.5 . . ?
H14A C12A H16A 109.5 . . ?
H15A C12A H16A 109.5 . . ?
C1B O1B H1B 107.9(18) . . ?
C2B O2B H2B 106.1(17) . . ?
C4B O3B C3B 116.96(15) . . ?
C1A O1A H1A 107.4(15) . . ?
C2A O2A H2A 105.1(14) . . ?
C4A O3A C3A 116.82(14) . . ?
C5A C10A C12A 112.12(17) . . ?
C5A C10A C11A 110.59(16) . . ?
C12A C10A C11A 110.61(19) . . ?
C5A C10A H13A 107.8 . . ?
C12A C10A H13A 107.8 . . ?
C11A C10A H13A 107.8 . . ?

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
O1B C1B C2B O2B -62.6(2) . . . . ?
O1B C1B C2B C3B 179.18(15) . . . . ?
O2B C2B C3B O3B 176.43(14) . . . . ?
C1B C2B C3B O3B -62.9(2) . . . . ?
C9C C4B C5B C6B -19.4(11) . . . . ?
O3B C4B C5B C6B 176.3(5) . . . . ?
C9B C4B C5B C6B -7.7(12) . . . . ?
C5C C4B C5B C6B 97(2) . . . . ?
C9C C4B C5B C10B 163.2(10) . . . . ?
O3B C4B C5B C10B -1.1(6) . . . . ?
C9B C4B C5B C10B 174.9(10) . . . . ?
C5C C4B C5B C10B -80(2) . . . . ?
C4B C5B C6B C7B 7.4(15) . . . . ?
C10B C5B C6B C7B -175.2(12) . . . . ?
C5B C6B C7B C8B -5(3) . . . . ?
C6B C7B C8B C9B 2(4) . . . . ?
C5B C4B C9B C8B 5(2) . . . . ?
C9C C4B C9B C8B 65(10) . . . . ?
O3B C4B C9B C8B -179.2(13) . . . . ?
C5C C4B C9B C8B -18(2) . . . . ?
C7B C8B C9B C4B -2(3) . . . . ?
C4B C5B C10B C11B -158.2(5) . . . . ?
C6B C5B C10B C11B 24.4(8) . . . . ?
C4B C5B C10B C12B 75.1(6) . . . . ?
C6B C5B C10B C12B -102.4(7) . . . . ?
C5B C4B C5C C6C -70(2) . . . . ?
C9C C4B C5C C6C 2.5(10) . . . . ?
O3B C4B C5C C6C 179.7(5) . . . . ?
C9B C4B C5C C6C 16.9(11) . . . . ?
C5B C4B C5C C10C 107(2) . . . . ?
C9C C4B C5C C10C -180.0(9) . . . . ?
O3B C4B C5C C10C -2.8(7) . . . . ?
C9B C4B C5C C10C -165.6(9) . . . . ?
C4B C5C C6C C7C -1.8(17) . . . . ?
C10C C5C C6C C7C -179.3(15) . . . . ?
C5C C6C C7C C8C 1(3) . . . . ?
C6C C7C C8C C9C -2(3) . . . . ?
C7C C8C C9C C4B 2(3) . . . . ?
C5B C4B C9C C8C 17.2(19) . . . . ?
O3B C4B C9C C8C -179.9(12) . . . . ?
C9B C4B C9C C8C -108(12) . . . . ?
C5C C4B C9C C8C -3.1(19) . . . . ?
C6C C5C C10C C11C 80.7(7) . . . . ?
C4B C5C C10C C11C -96.6(7) . . . . ?
C6C C5C C10C C12C -43.4(8) . . . . ?
C4B C5C C10C C12C 139.3(5) . . . . ?
O1A C1A C2A O2A 62.2(2) . . . . ?
O1A C1A C2A C3A -179.59(15) . . . . ?
O2A C2A C3A O3A -176.40(14) . . . . ?
C1A C2A C3A O3A 63.0(2) . . . . ?
O3A C4A C5A C6A -179.03(15) . . . . ?
C9A C4A C5A C6A 0.1(3) . . . . ?
O3A C4A C5A C10A 2.2(2) . . . . ?
C9A C4A C5A C10A -178.71(17) . . . . ?
C4A C5A C6A C7A -0.3(3) . . . . ?
C10A C5A C6A C7A 178.54(18) . . . . ?
C5A C6A C7A C8A 0.6(3) . . . . ?
C6A C7A C8A C9A -0.7(3) . . . . ?
C7A C8A C9A C4A 0.5(3) . . . . ?
O3A C4A C9A C8A 178.85(16) . . . . ?
C5A C4A C9A C8A -0.2(3) . . . . ?
C5B C4B O3B C3B 164.3(3) . . . . ?
C9C C4B O3B C3B 2.0(8) . . . . ?
C9B C4B O3B C3B -11.7(9) . . . . ?
C5C C4B O3B C3B -175.0(3) . . . . ?
C2B C3B O3B C4B -178.29(15) . . . . ?
C5A C4A O3A C3A 176.06(15) . . . . ?
C9A C4A O3A C3A -3.0(2) . . . . ?
C2A C3A O3A C4A -176.15(14) . . . . ?
C6A C5A C10A C12A 44.4(3) . . . . ?
C4A C5A C10A C12A -136.80(19) . . . . ?
C6A C5A C10A C11A -79.5(2) . . . . ?
C4A C5A C10A C11A 99.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 983816'
#######################################################################
#
#                 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_bred_sm47pr2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 O3'
_chemical_formula_sum            'C12 H18 O3'
_chemical_formula_weight         210.26

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           Orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_symmetry_Int_Tables_number      45

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

_cell_length_a                   15.3830(19)
_cell_length_b                   20.014(3)
_cell_length_c                   7.6027(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2340.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1451
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      25.74

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9457
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4965
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2172
_reflns_number_gt                1707
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_chemical_absolute_configuration rm
_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)+(0.0391P)²+1.4284P] 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     SHELXL
_refine_ls_extinction_coef       0.0036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2172
_refine_ls_number_parameters     147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_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 0.83913(15) 0.99586(13) 0.8674(3) 0.0301(5) Uani 1 1 d . . .
H11 H 0.7876 0.9946 0.7895 0.036 Uiso 1 1 calc R . .
H12 H 0.8186 1.0042 0.9888 0.036 Uiso 1 1 calc R . .
C2 C 0.88461(16) 0.92875(12) 0.8609(4) 0.0312(6) Uani 1 1 d . . .
H20 H 0.9096 0.9233 0.7403 0.037 Uiso 1 1 calc R . .
C3 C 0.82422(17) 0.87180(12) 0.8926(3) 0.0330(6) Uani 1 1 d . . .
H31 H 0.8564 0.8290 0.8912 0.040 Uiso 1 1 calc R . .
H32 H 0.7954 0.8767 1.0083 0.040 Uiso 1 1 calc R . .
C4 C 0.69925(16) 0.82380(11) 0.7501(3) 0.0312(6) Uani 1 1 d . . .
C5 C 0.64063(15) 0.82784(11) 0.6102(3) 0.0300(6) Uani 1 1 d . . .
C6 C 0.57707(16) 0.77888(12) 0.6016(4) 0.0364(7) Uani 1 1 d . . .
H6 H 0.5357 0.7804 0.5090 0.044 Uiso 1 1 calc R . .
C7 C 0.57199(18) 0.72781(14) 0.7238(4) 0.0421(7) Uani 1 1 d . . .
H7 H 0.5275 0.6951 0.7144 0.051 Uiso 1 1 calc R . .
C8 C 0.63108(18) 0.72441(13) 0.8583(4) 0.0418(7) Uani 1 1 d . . .
H8 H 0.6281 0.6890 0.9412 0.050 Uiso 1 1 calc R . .
C9 C 0.69529(18) 0.77280(12) 0.8731(4) 0.0368(6) Uani 1 1 d . . .
H9 H 0.7361 0.7710 0.9668 0.044 Uiso 1 1 calc R . .
C10 C 0.64840(17) 0.88333(12) 0.4767(4) 0.0368(6) Uani 1 1 d . . .
H13 H 0.7119 0.8930 0.4639 0.044 Uiso 1 1 calc R . .
C11 C 0.6067(3) 0.94661(15) 0.5467(5) 0.0662(10) Uani 1 1 d . . .
H14 H 0.6270 0.9549 0.6669 0.099 Uiso 1 1 calc R . .
H15 H 0.5433 0.9414 0.5470 0.099 Uiso 1 1 calc R . .
H16 H 0.6227 0.9844 0.4715 0.099 Uiso 1 1 calc R . .
C12 C 0.6153(3) 0.86538(16) 0.2949(5) 0.0678(10) Uani 1 1 d . . .
H17 H 0.5520 0.8595 0.2989 0.102 Uiso 1 1 calc R . .
H18 H 0.6426 0.8237 0.2558 0.102 Uiso 1 1 calc R . .
H19 H 0.6297 0.9013 0.2124 0.102 Uiso 1 1 calc R . .
O1 O 0.89410(12) 1.04917(9) 0.8145(3) 0.0378(5) Uani 1 1 d . . .
O2 O 0.95431(11) 0.92631(9) 0.9828(3) 0.0339(4) Uani 1 1 d . . .
O3 O 0.76112(11) 0.87328(8) 0.7538(2) 0.0371(5) Uani 1 1 d . . .
H1 H 0.9328(18) 1.0484(13) 0.901(4) 0.033(8) Uiso 1 1 d . . .
H2 H 0.9275(18) 0.9317(13) 1.088(4) 0.036(8) Uiso 1 1 d . . .


_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 1.419(3) . ?
C1 C2 1.515(4) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 O2 1.418(3) . ?
C2 C3 1.490(3) . ?
C2 H20 1.0000 . ?
C3 O3 1.434(3) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O3 1.374(3) . ?
C4 C9 1.386(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.386(3) . ?
C5 C10 1.509(3) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.370(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.516(4) . ?
C10 C12 1.517(4) . ?
C10 H13 1.0000 . ?
C11 H14 0.9800 . ?
C11 H15 0.9800 . ?
C11 H16 0.9800 . ?
C12 H17 0.9800 . ?
C12 H18 0.9800 . ?
C12 H19 0.9800 . ?
O1 H1 0.89(3) . ?
O2 H2 0.91(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
O1 C1 C2 112.45(19) . . ?
O1 C1 H11 109.1 . . ?
C2 C1 H11 109.1 . . ?
O1 C1 H12 109.1 . . ?
C2 C1 H12 109.1 . . ?
H11 C1 H12 107.8 . . ?
O2 C2 C3 109.8(2) . . ?
O2 C2 C1 111.00(19) . . ?
C3 C2 C1 112.6(2) . . ?
O2 C2 H20 107.7 . . ?
C3 C2 H20 107.7 . . ?
C1 C2 H20 107.7 . . ?
O3 C3 C2 106.67(19) . . ?
O3 C3 H31 110.4 . . ?
C2 C3 H31 110.4 . . ?
O3 C3 H32 110.4 . . ?
C2 C3 H32 110.4 . . ?
H31 C3 H32 108.6 . . ?
O3 C4 C9 123.2(2) . . ?
O3 C4 C5 114.9(2) . . ?
C9 C4 C5 121.9(2) . . ?
C6 C5 C4 116.7(2) . . ?
C6 C5 C10 123.0(2) . . ?
C4 C5 C10 120.2(2) . . ?
C7 C6 C5 122.1(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C4 C9 C8 119.4(3) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C5 C10 C11 110.2(2) . . ?
C5 C10 C12 114.3(2) . . ?
C11 C10 C12 112.1(3) . . ?
C5 C10 H13 106.6 . . ?
C11 C10 H13 106.6 . . ?
C12 C10 H13 106.6 . . ?
C10 C11 H14 109.5 . . ?
C10 C11 H15 109.5 . . ?
H14 C11 H15 109.5 . . ?
C10 C11 H16 109.5 . . ?
H14 C11 H16 109.5 . . ?
H15 C11 H16 109.5 . . ?
C10 C12 H17 109.5 . . ?
C10 C12 H18 109.5 . . ?
H17 C12 H18 109.5 . . ?
C10 C12 H19 109.5 . . ?
H17 C12 H19 109.5 . . ?
H18 C12 H19 109.5 . . ?
C1 O1 H1 100.1(17) . . ?
C2 O2 H2 103.3(18) . . ?
C4 O3 C3 117.96(19) . . ?

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 64.1(3) . . . . ?
O1 C1 C2 C3 -172.2(2) . . . . ?
O2 C2 C3 O3 -173.90(19) . . . . ?
C1 C2 C3 O3 61.8(3) . . . . ?
O3 C4 C5 C6 -180.0(2) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
O3 C4 C5 C10 0.3(3) . . . . ?
C9 C4 C5 C10 -178.6(2) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C10 C5 C6 C7 178.9(2) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
O3 C4 C9 C8 -179.3(2) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C7 C8 C9 C4 -0.6(4) . . . . ?
C6 C5 C10 C11 98.8(3) . . . . ?
C4 C5 C10 C11 -81.5(3) . . . . ?
C6 C5 C10 C12 -28.5(4) . . . . ?
C4 C5 C10 C12 151.2(3) . . . . ?
C9 C4 O3 C3 -0.3(3) . . . . ?
C5 C4 O3 C3 -179.2(2) . . . . ?
C2 C3 O3 C4 177.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 983817'
