# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Alexander Bredikhin'
_publ_contact_author_email       BAA@IOPC.KNC.RU

_publ_section_title              
;
p-Tolyl glycerol ether: is it possible to find more
simple molecular organogelator with pronounced chirality driven properties?
;
loop_
_publ_author_name
'Alexander Bredikhin'
'Flyura S. Akhatova'
'Zemfira A. Bredikhina'
'Aidar T. Gubaidullin'

# Attachment 'rac_7.cif'

data_rac_7
_database_code_depnum_ccdc_archive 'CCDC 755204'
#TrackingRef 'rac_7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O3'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.21

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 -2yc'
_symmetry_space_group_name_H-M   'P c'
_symmetry_Int_Tables_number      7

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

_cell_length_a                   17.264(2)
_cell_length_b                   4.7225(7)
_cell_length_c                   11.9008(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.091(2)
_cell_angle_gamma                90.00
_cell_volume                     970.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2690
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9567
_exptl_absorpt_correction_T_max  0.9973
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12167
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.94
_reflns_number_total             2236
_reflns_number_gt                1597
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_chemical_absolute_configuration unk
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1673P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2236
_refine_ls_number_parameters     238
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2257
_refine_ls_wR_factor_gt          0.2048
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.4649(2) 1.1510(8) 0.7256(3) 0.0580(9) Uani 1 1 d . . .
H1A H 0.4376 1.2409 0.7692 0.087 Uiso 1 1 calc R . .
C1A C 0.5142(3) 0.9656(12) 0.7876(4) 0.0502(11) Uani 1 1 d . . .
H11A H 0.5591 1.0715 0.8132 0.060 Uiso 1 1 calc R . .
H12A H 0.5326 0.8174 0.7378 0.060 Uiso 1 1 calc R . .
O2A O 0.4245(2) 0.6157(9) 0.8455(4) 0.0618(10) Uani 1 1 d . . .
H2A H 0.3910 0.5821 0.8924 0.093 Uiso 1 1 calc R . .
C2A C 0.4756(3) 0.8307(10) 0.8877(5) 0.0490(11) Uani 1 1 d . . .
H21A H 0.4444 0.9750 0.9258 0.059 Uiso 1 1 calc R . .
O3A O 0.5894(2) 0.5421(8) 0.9138(3) 0.0512(8) Uani 1 1 d . . .
C3A C 0.5345(4) 0.7136(12) 0.9713(4) 0.0552(13) Uani 1 1 d . . .
H31A H 0.5609 0.8687 1.0087 0.066 Uiso 1 1 calc R . .
H32A H 0.5081 0.6018 1.0279 0.066 Uiso 1 1 calc R . .
C4A C 0.6450(3) 0.4141(11) 0.9762(4) 0.0455(10) Uani 1 1 d . . .
C5A C 0.6510(3) 0.4368(13) 1.0931(5) 0.0554(12) Uani 1 1 d . . .
H5A H 0.6171 0.5504 1.1337 0.066 Uiso 1 1 calc R . .
C6A C 0.7101(4) 0.2821(12) 1.1476(5) 0.0580(13) Uani 1 1 d . . .
H6A H 0.7138 0.2921 1.2255 0.070 Uiso 1 1 calc R . .
C7A C 0.7623(3) 0.1177(12) 1.0904(4) 0.0528(12) Uani 1 1 d . . .
C8A C 0.7562(3) 0.1029(12) 0.9740(5) 0.0547(12) Uani 1 1 d . . .
H8A H 0.7909 -0.0070 0.9333 0.066 Uiso 1 1 calc R . .
C9A C 0.6978(3) 0.2534(12) 0.9178(4) 0.0524(12) Uani 1 1 d . . .
H9A H 0.6947 0.2444 0.8399 0.063 Uiso 1 1 calc R . .
C10A C 0.8263(5) -0.0337(16) 1.1499(6) 0.0720(16) Uani 1 1 d . . .
H13A H 0.8559 -0.1409 1.0966 0.108 Uiso 1 1 calc R . .
H14A H 0.8047 -0.1593 1.2051 0.108 Uiso 1 1 calc R . .
H15A H 0.8593 0.1018 1.1864 0.108 Uiso 1 1 calc R . .
O1B O 0.3089(3) 0.6052(9) 0.4726(4) 0.0651(11) Uani 1 1 d . . .
H1B H 0.3100 0.7693 0.4951 0.098 Uiso 1 1 calc R . .
C1B C 0.2533(3) 0.4492(13) 0.5352(5) 0.0563(13) Uani 1 1 d . . .
H11B H 0.2296 0.3080 0.4870 0.068 Uiso 1 1 calc R . .
H12B H 0.2129 0.5763 0.5608 0.068 Uiso 1 1 calc R . .
C2B C 0.2899(3) 0.3032(13) 0.6362(5) 0.0545(12) Uani 1 1 d . . .
H21B H 0.3226 0.4421 0.6749 0.065 Uiso 1 1 calc R . .
O2B O 0.3386(2) 0.0803(9) 0.5981(4) 0.0630(11) Uani 1 1 d . . .
H2B H 0.3775 0.1475 0.5689 0.095 Uiso 1 1 calc R . .
C3B C 0.2307(3) 0.1960(12) 0.7193(5) 0.0583(13) Uani 1 1 d . . .
H31B H 0.2560 0.0836 0.7768 0.070 Uiso 1 1 calc R . .
H32B H 0.2051 0.3545 0.7554 0.070 Uiso 1 1 calc R . .
O3B O 0.1748(2) 0.0263(9) 0.6606(3) 0.0540(9) Uani 1 1 d . . .
C4B C 0.1182(3) -0.0971(11) 0.7247(5) 0.0525(12) Uani 1 1 d . . .
C5B C 0.0674(3) -0.2718(14) 0.6633(4) 0.0562(13) Uani 1 1 d . . .
H5B H 0.0728 -0.2942 0.5861 0.067 Uiso 1 1 calc R . .
C6B C 0.0090(4) -0.4094(14) 0.7216(5) 0.0615(14) Uani 1 1 d . . .
H6B H -0.0252 -0.5241 0.6817 0.074 Uiso 1 1 calc R . .
C7B C -0.0007(3) -0.3831(12) 0.8368(5) 0.0553(13) Uani 1 1 d . . .
C8B C 0.0498(4) -0.2185(15) 0.8925(5) 0.0651(15) Uani 1 1 d . . .
H8B H 0.0459 -0.2055 0.9702 0.078 Uiso 1 1 calc R . .
C9B C 0.1085(4) -0.0643(12) 0.8374(5) 0.0580(13) Uani 1 1 d . . .
H9B H 0.1403 0.0583 0.8776 0.070 Uiso 1 1 calc R . .
C10B C -0.0642(4) -0.5411(19) 0.8969(6) 0.0751(17) Uani 1 1 d . . .
H13B H -0.0938 -0.6481 0.8434 0.113 Uiso 1 1 calc R . .
H14B H -0.0975 -0.4084 0.9343 0.113 Uiso 1 1 calc R . .
H15B H -0.0418 -0.6672 0.9512 0.113 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.063(2) 0.055(2) 0.056(2) -0.0016(17) -0.0034(17) 0.0086(17)
C1A 0.046(2) 0.052(3) 0.053(3) 0.000(2) 0.001(2) 0.004(2)
O2A 0.050(2) 0.061(2) 0.075(3) -0.009(2) 0.0092(17) -0.0075(17)
C2A 0.046(2) 0.037(2) 0.064(3) -0.003(2) 0.011(2) 0.0030(19)
O3A 0.0553(18) 0.0553(19) 0.0430(17) 0.0015(16) 0.0033(14) 0.0090(16)
C3A 0.072(3) 0.043(3) 0.051(3) 0.004(2) 0.016(2) 0.014(2)
C4A 0.043(2) 0.045(3) 0.049(2) 0.004(2) 0.0020(18) -0.0054(19)
C5A 0.060(3) 0.059(3) 0.047(3) -0.001(2) 0.003(2) -0.001(2)
C6A 0.077(4) 0.049(3) 0.048(2) 0.000(2) -0.005(2) -0.004(3)
C7A 0.053(3) 0.052(3) 0.053(3) 0.012(2) -0.011(2) -0.006(2)
C8A 0.044(2) 0.058(3) 0.061(3) 0.006(3) 0.003(2) 0.003(2)
C9A 0.047(2) 0.057(3) 0.054(3) -0.003(2) 0.000(2) 0.001(2)
C10A 0.078(4) 0.070(4) 0.068(4) 0.010(3) -0.014(3) 0.007(3)
O1B 0.073(2) 0.054(2) 0.068(2) -0.002(2) 0.015(2) -0.004(2)
C1B 0.037(2) 0.068(3) 0.064(3) -0.008(3) -0.001(2) 0.000(2)
C2B 0.048(2) 0.056(3) 0.060(3) -0.007(2) -0.003(2) -0.002(2)
O2B 0.053(2) 0.055(2) 0.081(3) -0.013(2) -0.0079(19) 0.0030(18)
C3B 0.061(3) 0.053(3) 0.061(3) -0.010(3) -0.011(2) -0.001(3)
O3B 0.0521(19) 0.062(2) 0.0483(18) -0.0019(17) 0.0000(15) -0.0079(17)
C4B 0.053(3) 0.046(3) 0.058(3) 0.000(2) -0.004(2) 0.005(2)
C5B 0.052(3) 0.070(3) 0.046(2) 0.001(3) -0.006(2) 0.000(2)
C6B 0.055(3) 0.070(4) 0.060(3) -0.007(3) -0.004(2) 0.002(3)
C7B 0.060(3) 0.050(3) 0.056(3) 0.008(2) 0.005(2) 0.005(2)
C8B 0.077(4) 0.070(4) 0.047(3) -0.001(3) 0.006(3) 0.005(3)
C9B 0.066(3) 0.054(3) 0.055(3) -0.002(2) -0.009(2) 0.003(3)
C10B 0.064(3) 0.096(5) 0.066(3) 0.004(4) 0.005(3) -0.006(4)

_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 1.427(7) . ?
O1A H1A 0.8200 . ?
C1A C2A 1.508(7) . ?
C1A H11A 0.9700 . ?
C1A H12A 0.9700 . ?
O2A C2A 1.435(7) . ?
O2A H2A 0.8200 . ?
C2A C3A 1.525(8) . ?
C2A H21A 0.9800 . ?
O3A C4A 1.355(6) . ?
O3A C3A 1.423(6) . ?
C3A H31A 0.9700 . ?
C3A H32A 0.9700 . ?
C4A C9A 1.376(7) . ?
C4A C5A 1.399(8) . ?
C5A C6A 1.412(9) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.371(8) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.391(8) . ?
C7A C10A 1.494(9) . ?
C8A C9A 1.402(8) . ?
C8A H8A 0.9300 . ?
C9A H9A 0.9300 . ?
C10A H13A 0.9600 . ?
C10A H14A 0.9600 . ?
C10A H15A 0.9600 . ?
O1B C1B 1.422(7) . ?
O1B H1B 0.8200 . ?
C1B C2B 1.522(9) . ?
C1B H11B 0.9700 . ?
C1B H12B 0.9700 . ?
C2B O2B 1.421(7) . ?
C2B C3B 1.511(8) . ?
C2B H21B 0.9800 . ?
O2B H2B 0.8200 . ?
C3B O3B 1.435(7) . ?
C3B H31B 0.9700 . ?
C3B H32B 0.9700 . ?
O3B C4B 1.370(7) . ?
C4B C9B 1.360(8) . ?
C4B C5B 1.408(8) . ?
C5B C6B 1.386(9) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.388(9) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.342(9) . ?
C7B C10B 1.507(9) . ?
C8B C9B 1.411(9) . ?
C8B H8B 0.9300 . ?
C9B H9B 0.9300 . ?
C10B H13B 0.9600 . ?
C10B H14B 0.9600 . ?
C10B H15B 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 109.5 . . ?
O1A C1A C2A 113.8(4) . . ?
O1A C1A H11A 108.8 . . ?
C2A C1A H11A 108.8 . . ?
O1A C1A H12A 108.8 . . ?
C2A C1A H12A 108.8 . . ?
H11A C1A H12A 107.7 . . ?
C2A O2A H2A 109.5 . . ?
O2A C2A C1A 107.2(5) . . ?
O2A C2A C3A 112.4(4) . . ?
C1A C2A C3A 111.9(4) . . ?
O2A C2A H21A 108.4 . . ?
C1A C2A H21A 108.4 . . ?
C3A C2A H21A 108.4 . . ?
C4A O3A C3A 117.5(4) . . ?
O3A C3A C2A 109.7(4) . . ?
O3A C3A H31A 109.7 . . ?
C2A C3A H31A 109.7 . . ?
O3A C3A H32A 109.7 . . ?
C2A C3A H32A 109.7 . . ?
H31A C3A H32A 108.2 . . ?
O3A C4A C9A 116.0(4) . . ?
O3A C4A C5A 124.2(5) . . ?
C9A C4A C5A 119.8(5) . . ?
C4A C5A C6A 118.0(5) . . ?
C4A C5A H5A 121.0 . . ?
C6A C5A H5A 121.0 . . ?
C7A C6A C5A 122.7(5) . . ?
C7A C6A H6A 118.7 . . ?
C5A C6A H6A 118.7 . . ?
C6A C7A C8A 118.3(5) . . ?
C6A C7A C10A 121.4(5) . . ?
C8A C7A C10A 120.2(6) . . ?
C7A C8A C9A 120.2(5) . . ?
C7A C8A H8A 119.9 . . ?
C9A C8A H8A 119.9 . . ?
C4A C9A C8A 121.0(5) . . ?
C4A C9A H9A 119.5 . . ?
C8A C9A H9A 119.5 . . ?
C7A C10A H13A 109.5 . . ?
C7A C10A H14A 109.5 . . ?
H13A C10A H14A 109.5 . . ?
C7A C10A H15A 109.5 . . ?
H13A C10A H15A 109.5 . . ?
H14A C10A H15A 109.5 . . ?
C1B O1B H1B 109.5 . . ?
O1B C1B C2B 111.6(5) . . ?
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 111.2(5) . . ?
O2B C2B C1B 109.2(4) . . ?
C3B C2B C1B 112.8(4) . . ?
O2B C2B H21B 107.8 . . ?
C3B C2B H21B 107.8 . . ?
C1B C2B H21B 107.8 . . ?
C2B O2B H2B 109.5 . . ?
O3B C3B C2B 108.9(5) . . ?
O3B C3B H31B 109.9 . . ?
C2B C3B H31B 109.9 . . ?
O3B C3B H32B 109.9 . . ?
C2B C3B H32B 109.9 . . ?
H31B C3B H32B 108.3 . . ?
C4B O3B C3B 116.5(4) . . ?
C9B C4B O3B 126.1(5) . . ?
C9B C4B C5B 120.1(5) . . ?
O3B C4B C5B 113.8(5) . . ?
C6B C5B C4B 117.9(5) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
C5B C6B C7B 122.8(6) . . ?
C5B C6B H6B 118.6 . . ?
C7B C6B H6B 118.6 . . ?
C8B C7B C6B 117.4(5) . . ?
C8B C7B C10B 121.7(6) . . ?
C6B C7B C10B 120.9(6) . . ?
C7B C8B C9B 122.4(5) . . ?
C7B C8B H8B 118.8 . . ?
C9B C8B H8B 118.8 . . ?
C4B C9B C8B 119.3(5) . . ?
C4B C9B H9B 120.4 . . ?
C8B C9B H9B 120.4 . . ?
C7B C10B H13B 109.5 . . ?
C7B C10B H14B 109.5 . . ?
H13B C10B H14B 109.5 . . ?
C7B C10B H15B 109.5 . . ?
H13B C10B H15B 109.5 . . ?
H14B C10B H15B 109.5 . . ?

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 74.6(5) . . . . ?
O1A C1A C2A C3A -161.8(4) . . . . ?
C4A O3A C3A C2A -178.2(4) . . . . ?
O2A C2A C3A O3A 70.6(5) . . . . ?
C1A C2A C3A O3A -50.0(6) . . . . ?
C3A O3A C4A C9A -179.1(4) . . . . ?
C3A O3A C4A C5A 1.0(7) . . . . ?
O3A C4A C5A C6A 177.4(5) . . . . ?
C9A C4A C5A C6A -2.5(8) . . . . ?
C4A C5A C6A C7A 1.5(9) . . . . ?
C5A C6A C7A C8A -0.2(9) . . . . ?
C5A C6A C7A C10A 177.4(6) . . . . ?
C6A C7A C8A C9A -0.1(8) . . . . ?
C10A C7A C8A C9A -177.7(5) . . . . ?
O3A C4A C9A C8A -177.7(5) . . . . ?
C5A C4A C9A C8A 2.3(8) . . . . ?
C7A C8A C9A C4A -1.0(8) . . . . ?
O1B C1B C2B O2B -69.7(6) . . . . ?
O1B C1B C2B C3B 166.1(4) . . . . ?
O2B C2B C3B O3B -70.9(6) . . . . ?
C1B C2B C3B O3B 52.1(6) . . . . ?
C2B C3B O3B C4B 177.6(4) . . . . ?
C3B O3B C4B C9B 2.8(8) . . . . ?
C3B O3B C4B C5B -177.0(4) . . . . ?
C9B C4B C5B C6B -0.9(8) . . . . ?
O3B C4B C5B C6B 179.0(5) . . . . ?
C4B C5B C6B C7B -0.5(9) . . . . ?
C5B C6B C7B C8B -0.6(9) . . . . ?
C5B C6B C7B C10B -178.9(6) . . . . ?
C6B C7B C8B C9B 3.1(9) . . . . ?
C10B C7B C8B C9B -178.6(6) . . . . ?
O3B C4B C9B C8B -176.5(5) . . . . ?
C5B C4B C9B C8B 3.3(8) . . . . ?
C7B C8B C9B C4B -4.6(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.99
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.076

# Attachment 'scal_S_7.cif'

data_scal_S_7
_database_code_depnum_ccdc_archive 'CCDC 755205'
#TrackingRef 'scal_S_7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O3'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_weight         182.21

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_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                   4.8768(2)
_cell_length_b                   7.2147(3)
_cell_length_c                   28.5203(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1003.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6289
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      67.13

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_T_max  0.9052
_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      296(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       'phi and omega scans'
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7867
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         6.21
_diffrn_reflns_theta_max         67.35
_reflns_number_total             1673
_reflns_number_gt                1630
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_chemical_absolute_configuration rmad
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.0862P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    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   0.0(2)
_refine_ls_number_reflns         1673
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.4593(3) 0.69819(17) 0.80816(5) 0.0545(3) Uani 1 1 d . . .
H11 H 0.3744 0.7375 0.8373 0.065 Uiso 1 1 calc R . .
H12 H 0.5803 0.7965 0.7976 0.065 Uiso 1 1 calc R . .
C2 C 0.6234(3) 0.52472(17) 0.81657(4) 0.0471(3) Uani 1 1 d . . .
H21 H 0.7476 0.5465 0.8430 0.057 Uiso 1 1 calc R . .
C3 C 0.4483(3) 0.35742(17) 0.82758(5) 0.0482(3) Uani 1 1 d . . .
H31 H 0.3366 0.3247 0.8007 0.058 Uiso 1 1 calc R . .
H32 H 0.5631 0.2522 0.8355 0.058 Uiso 1 1 calc R . .
C4 C 0.1170(3) 0.26998(18) 0.88514(4) 0.0495(3) Uani 1 1 d . . .
C5 C -0.0339(3) 0.3198(2) 0.92417(5) 0.0650(4) Uani 1 1 d . . .
H5 H -0.0207 0.4395 0.9361 0.078 Uiso 1 1 calc R . .
C6 C -0.2037(4) 0.1929(3) 0.94546(5) 0.0725(4) Uani 1 1 d . . .
H6 H -0.3049 0.2289 0.9716 0.087 Uiso 1 1 calc R . .
C7 C -0.2280(3) 0.0126(2) 0.92904(5) 0.0651(4) Uani 1 1 d . . .
C8 C -0.0769(3) -0.0331(2) 0.89003(6) 0.0640(4) Uani 1 1 d . . .
H8 H -0.0892 -0.1531 0.8783 0.077 Uiso 1 1 calc R . .
C9 C 0.0935(3) 0.0927(2) 0.86741(5) 0.0570(3) Uani 1 1 d . . .
H9 H 0.1903 0.0580 0.8407 0.068 Uiso 1 1 calc R . .
C10 C -0.4123(4) -0.1254(3) 0.95305(7) 0.0917(6) Uani 1 1 d . . .
H13 H -0.4262 -0.2353 0.9342 0.138 Uiso 1 1 calc R . .
H14 H -0.5912 -0.0722 0.9571 0.138 Uiso 1 1 calc R . .
H15 H -0.3370 -0.1566 0.9831 0.138 Uiso 1 1 calc R . .
O1 O 0.2538(2) 0.66670(15) 0.77392(4) 0.0731(3) Uani 1 1 d . . .
O2 O 0.7826(2) 0.47561(14) 0.77670(4) 0.0624(3) Uani 1 1 d . . .
O3 O 0.2787(2) 0.40637(12) 0.86629(3) 0.0564(3) Uani 1 1 d . . .
H1 H 0.234(4) 0.761(3) 0.7573(6) 0.080(5) Uiso 1 1 d . . .
H2 H 0.937(4) 0.544(3) 0.7761(6) 0.083(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0462(7) 0.0454(6) 0.0720(8) 0.0042(6) 0.0013(6) -0.0004(6)
C2 0.0374(6) 0.0470(6) 0.0570(7) -0.0064(5) -0.0039(5) 0.0003(5)
C3 0.0424(6) 0.0437(6) 0.0586(7) -0.0031(5) 0.0005(6) 0.0041(5)
C4 0.0452(6) 0.0501(6) 0.0530(6) 0.0048(5) -0.0023(6) 0.0050(6)
C5 0.0731(10) 0.0669(9) 0.0550(8) -0.0043(7) 0.0048(7) 0.0025(8)
C6 0.0686(10) 0.0926(12) 0.0563(7) 0.0049(8) 0.0099(7) 0.0005(10)
C7 0.0486(7) 0.0814(10) 0.0653(8) 0.0194(7) -0.0070(7) -0.0042(9)
C8 0.0549(8) 0.0563(8) 0.0808(9) 0.0058(7) -0.0025(8) -0.0041(7)
C9 0.0505(7) 0.0522(7) 0.0683(8) -0.0017(6) 0.0056(7) 0.0027(6)
C10 0.0713(11) 0.1118(15) 0.0922(12) 0.0353(11) -0.0001(10) -0.0186(12)
O1 0.0462(5) 0.0702(6) 0.1030(8) 0.0365(6) -0.0181(6) -0.0143(6)
O2 0.0427(5) 0.0630(6) 0.0815(7) -0.0221(5) 0.0115(5) -0.0113(5)
O3 0.0610(6) 0.0467(4) 0.0615(5) -0.0028(4) 0.0093(5) 0.0009(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.4178(17) . ?
C1 C2 1.5046(17) . ?
C1 H11 0.9700 . ?
C1 H12 0.9700 . ?
C2 O2 1.4218(16) . ?
C2 C3 1.5114(18) . ?
C2 H21 0.9800 . ?
C3 O3 1.4240(15) . ?
C3 H31 0.9700 . ?
C3 H32 0.9700 . ?
C4 O3 1.3709(16) . ?
C4 C9 1.380(2) . ?
C4 C5 1.3822(19) . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(2) . ?
C7 C10 1.506(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H13 0.9600 . ?
C10 H14 0.9600 . ?
C10 H15 0.9600 . ?
O1 H1 0.836(19) . ?
O2 H2 0.90(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 110.63(11) . . ?
O1 C1 H11 109.5 . . ?
C2 C1 H11 109.5 . . ?
O1 C1 H12 109.5 . . ?
C2 C1 H12 109.5 . . ?
H11 C1 H12 108.1 . . ?
O2 C2 C1 111.73(11) . . ?
O2 C2 C3 106.00(10) . . ?
C1 C2 C3 113.40(10) . . ?
O2 C2 H21 108.5 . . ?
C1 C2 H21 108.5 . . ?
C3 C2 H21 108.5 . . ?
O3 C3 C2 106.92(10) . . ?
O3 C3 H31 110.3 . . ?
C2 C3 H31 110.3 . . ?
O3 C3 H32 110.3 . . ?
C2 C3 H32 110.3 . . ?
H31 C3 H32 108.6 . . ?
O3 C4 C9 124.70(12) . . ?
O3 C4 C5 115.82(12) . . ?
C9 C4 C5 119.47(13) . . ?
C6 C5 C4 120.18(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.77(15) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 116.88(14) . . ?
C8 C7 C10 121.99(18) . . ?
C6 C7 C10 121.13(17) . . ?
C7 C8 C9 122.68(15) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C4 C9 C8 119.00(14) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C7 C10 H13 109.5 . . ?
C7 C10 H14 109.5 . . ?
H13 C10 H14 109.5 . . ?
C7 C10 H15 109.5 . . ?
H13 C10 H15 109.5 . . ?
H14 C10 H15 109.5 . . ?
C1 O1 H1 109.8(13) . . ?
C2 O2 H2 109.8(11) . . ?
C4 O3 C3 117.40(10) . . ?

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 67.33(13) . . . . ?
O1 C1 C2 C3 -52.39(15) . . . . ?
O2 C2 C3 O3 -177.66(9) . . . . ?
C1 C2 C3 O3 -54.73(14) . . . . ?
O3 C4 C5 C6 179.63(13) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C5 C6 C7 C10 179.29(15) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C10 C7 C8 C9 179.85(15) . . . . ?
O3 C4 C9 C8 179.66(12) . . . . ?
C5 C4 C9 C8 -1.6(2) . . . . ?
C7 C8 C9 C4 1.2(2) . . . . ?
C9 C4 O3 C3 -4.45(18) . . . . ?
C5 C4 O3 C3 176.73(11) . . . . ?
C2 C3 O3 C4 -174.70(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        67.35
_diffrn_measured_fraction_theta_full 0.99
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.096
_refine_diff_density_rms         0.025