data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Edwin Weber'
_publ_contact_author_address     
;
Institut fur Organische Chemie
Universitat Bergakademie Freiberg
Leipziger Str 29
Freiberg/Sachsen
D-09596
GERMANY
;

_publ_contact_author_email       EDWIN.WEBER@CHEMIE.TU-FREIBERG.DE

_publ_section_title              
;
Oligofunctional amphiphiles featuring geometric core
group preorganization: synthesis and study of Langmuir and
Langmuir-Blodgett films
;
loop_
_publ_author_name
'Edwin Weber'
'Petra U. Muller'
'Gerd Rheinwald'
'Wihelm Seichter'

data_m126cory
_database_code_depnum_ccdc_archive 'CCDC 278011'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 O8 S2'
_chemical_formula_weight         610.71

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3831(8)
_cell_length_b                   9.6997(9)
_cell_length_c                   10.2470(9)
_cell_angle_alpha                117.460(2)
_cell_angle_beta                 95.4470(10)
_cell_angle_gamma                106.7540(10)
_cell_volume                     763.39(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plateless
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_T_max  0.9911

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5642
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         30.40
_reflns_number_total             3717
_reflns_number_gt                2164
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINT
_computing_data_reduction        ABSEN
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ZORTEP
_computing_publication_material  SHELX-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^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         3717
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97517(9) 0.70762(11) 0.32190(9) 0.0380(2) Uani 1 d . . .
O1 O 0.6545(3) 0.8936(3) 0.4740(3) 0.0446(6) Uani 1 d . . .
H1 H 0.7157 0.8505 0.4324 0.067 Uiso 1 calc R . .
O2 O 0.7722(2) 0.5123(3) 0.6392(2) 0.0423(6) Uani 1 d . . .
O3 O 0.6183(2) 0.5051(3) 0.7921(2) 0.0374(5) Uani 1 d . . .
O4 O 0.8450(3) 0.7691(3) 0.3233(2) 0.0449(6) Uani 1 d . . .
C1 C 0.6102(3) 0.8384(4) 0.5693(3) 0.0302(6) Uani 1 d . . .
C2 C 0.6622(3) 0.7278(4) 0.5883(3) 0.0287(6) Uani 1 d . . .
H2 H 0.7306 0.6870 0.5325 0.034 Uiso 1 calc R . .
C3 C 0.6162(3) 0.6758(3) 0.6874(3) 0.0263(6) Uani 1 d . . .
C4 C 0.5154(3) 0.7338(3) 0.7694(3) 0.0272(6) Uani 1 d . . .
H4 H 0.4845 0.6995 0.8387 0.033 Uiso 1 calc R . .
C5 C 0.4604(3) 0.8435(3) 0.7481(3) 0.0256(6) Uani 1 d . . .
C6 C 0.5081(3) 0.8964(4) 0.6493(3) 0.0296(6) Uani 1 d . . .
H6 H 0.4714 0.9720 0.6362 0.036 Uiso 1 calc R . .
C7 C 0.6782(3) 0.5575(4) 0.7026(3) 0.0318(7) Uani 1 d . . .
C8 C 0.6733(4) 0.3885(4) 0.8113(4) 0.0435(8) Uani 1 d . . .
H8A H 0.7854 0.4426 0.8627 0.052 Uiso 1 calc R . .
H8B H 0.6555 0.2888 0.7107 0.052 Uiso 1 calc R . .
C9 C 0.5848(4) 0.3384(4) 0.9067(4) 0.0481(9) Uani 1 d . . .
H9A H 0.6188 0.2593 0.9223 0.072 Uiso 1 calc R . .
H9B H 0.4742 0.2850 0.8545 0.072 Uiso 1 calc R . .
H9C H 0.6034 0.4381 1.0058 0.072 Uiso 1 calc R . .
C10 C 0.3493(3) 0.8976(3) 0.8267(3) 0.0271(6) Uani 1 d . . .
C11 C 0.2515(3) 0.9334(4) 0.8835(3) 0.0301(6) Uani 1 d . . .
C12 C 0.1254(3) 0.9693(3) 0.9451(3) 0.0270(6) Uani 1 d . . .
C13 C 0.0646(3) 0.9038(4) 1.0321(3) 0.0318(7) Uani 1 d . . .
H13 H 0.1087 0.8376 1.0541 0.038 Uiso 1 calc R . .
C14 C -0.0592(3) 0.9336(4) 1.0869(3) 0.0324(7) Uani 1 d . . .
H14 H -0.0994 0.8881 1.1463 0.039 Uiso 1 calc R . .
C15 C 0.8891(4) 0.4950(4) 0.2722(4) 0.0529(10) Uani 1 d . . .
H15A H 0.8279 0.4269 0.1654 0.079 Uiso 1 calc R . .
H15B H 0.8218 0.4868 0.3380 0.079 Uiso 1 calc R . .
H15C H 0.9701 0.4541 0.2860 0.079 Uiso 1 calc R . .
C16 C 1.0720(4) 0.7876(4) 0.5143(3) 0.0440(8) Uani 1 d . . .
H16A H 1.1291 0.9087 0.5641 0.066 Uiso 1 calc R . .
H16B H 1.1442 0.7326 0.5164 0.066 Uiso 1 calc R . .
H16C H 0.9961 0.7655 0.5686 0.066 Uiso 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
S1 0.0388(4) 0.0483(5) 0.0421(5) 0.0267(4) 0.0216(3) 0.0269(4)
O1 0.0553(14) 0.0653(16) 0.0603(14) 0.0508(13) 0.0417(12) 0.0441(13)
O2 0.0441(13) 0.0569(15) 0.0564(14) 0.0382(12) 0.0292(11) 0.0383(12)
O3 0.0444(12) 0.0494(14) 0.0480(13) 0.0362(11) 0.0255(10) 0.0331(11)
O4 0.0534(14) 0.0636(16) 0.0536(14) 0.0411(12) 0.0334(11) 0.0439(13)
C1 0.0316(15) 0.0355(17) 0.0335(15) 0.0213(13) 0.0148(12) 0.0176(14)
C2 0.0270(14) 0.0382(17) 0.0322(15) 0.0208(14) 0.0156(12) 0.0201(14)
C3 0.0246(14) 0.0289(16) 0.0305(15) 0.0167(12) 0.0104(11) 0.0131(12)
C4 0.0260(14) 0.0315(16) 0.0288(14) 0.0168(13) 0.0121(11) 0.0134(13)
C5 0.0245(14) 0.0267(15) 0.0277(14) 0.0124(12) 0.0110(11) 0.0137(13)
C6 0.0307(15) 0.0330(17) 0.0366(16) 0.0209(14) 0.0157(12) 0.0197(14)
C7 0.0308(15) 0.0378(18) 0.0380(16) 0.0227(14) 0.0151(13) 0.0201(14)
C8 0.052(2) 0.056(2) 0.056(2) 0.0412(18) 0.0260(16) 0.0393(19)
C9 0.066(2) 0.052(2) 0.049(2) 0.0349(18) 0.0224(17) 0.034(2)
C10 0.0305(15) 0.0284(16) 0.0282(14) 0.0161(13) 0.0105(11) 0.0155(13)
C11 0.0348(16) 0.0295(16) 0.0298(15) 0.0148(13) 0.0115(12) 0.0169(14)
C12 0.0310(15) 0.0299(16) 0.0249(14) 0.0122(12) 0.0138(11) 0.0189(14)
C13 0.0383(17) 0.0352(18) 0.0357(16) 0.0211(14) 0.0182(13) 0.0245(15)
C14 0.0395(17) 0.0394(18) 0.0357(16) 0.0237(14) 0.0242(13) 0.0254(15)
C15 0.0382(19) 0.033(2) 0.066(2) 0.0109(17) 0.0025(16) 0.0146(16)
C16 0.0408(19) 0.044(2) 0.0428(19) 0.0194(16) 0.0116(14) 0.0148(16)

_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
S1 O4 1.505(2) 1 ?
S1 O4 1.505(2) . ?
S1 C15 1.777(3) . ?
S1 C16 1.777(3) . ?
O1 C1 1.358(3) . ?
O1 H1 0.8400 . ?
O2 C7 1.209(3) . ?
O3 C7 1.333(3) . ?
O3 C8 1.451(3) . ?
O4 O4 0.000(13) 1 ?
C1 C2 1.380(4) . ?
C1 C6 1.393(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C7 1.487(4) . ?
C4 C5 1.398(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 C10 1.449(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.498(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.183(4) . ?
C11 C12 1.448(4) . ?
C12 C13 1.390(4) . ?
C12 C14 1.402(4) 2_577 ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C12 1.402(4) 2_577 ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O4 0.0(4) 1 . ?
O4 S1 C15 106.11(15) 1 . ?
O4 S1 C15 106.11(15) . . ?
O4 S1 C16 107.93(14) 1 . ?
O4 S1 C16 107.93(14) . . ?
C15 S1 C16 96.61(16) . . ?
C1 O1 H1 109.5 . . ?
C7 O3 C8 116.0(2) . . ?
O4 O4 S1 0(10) 1 . ?
O1 C1 C2 122.3(2) . . ?
O1 C1 C6 118.0(2) . . ?
C2 C1 C6 119.7(3) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 C7 117.6(2) . . ?
C4 C3 C7 122.1(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C10 120.1(2) . . ?
C4 C5 C10 119.4(2) . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O2 C7 O3 123.5(3) . . ?
O2 C7 C3 123.4(3) . . ?
O3 C7 C3 113.1(2) . . ?
O3 C8 C9 107.0(2) . . ?
O3 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O3 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 176.0(3) . . ?
C10 C11 C12 176.8(3) . . ?
C13 C12 C14 119.0(2) . 2_577 ?
C13 C12 C11 120.8(2) . . ?
C14 C12 C11 120.1(2) 2_577 . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C12 120.1(3) . 2_577 ?
C13 C14 H14 120.0 . . ?
C12 C14 H14 120.0 2_577 . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.84 1.83 2.662(3) 171.5 1
C6 H6 O1 0.95 2.52 3.446(3) 164.1 2_676
C15 H15C O2 0.98 2.35 3.251(4) 153.3 2_766
C16 H16B O2 0.98 2.57 3.426(4) 145.7 2_766

_diffrn_measured_fraction_theta_max 0.806
_diffrn_reflns_theta_full        30.40
_diffrn_measured_fraction_theta_full 0.806
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.061

data_5a
_database_code_depnum_ccdc_archive 'CCDC 278012'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H70 O6'
_chemical_formula_weight         791.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8583(5)
_cell_length_b                   9.1667(5)
_cell_length_c                   15.4654(4)
_cell_angle_alpha                88.4100(10)
_cell_angle_beta                 80.604(3)
_cell_angle_gamma                65.605(3)
_cell_volume                     1127.25(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   'multi scans'
_exptl_absorpt_correction_T_min  0.9561
_exptl_absorpt_correction_T_max  0.9924

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      93(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  'CCD area detector'
_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            6717
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         28.41
_reflns_number_total             6463
_reflns_number_gt                4243
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^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         6463
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1551
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33534(17) 0.48054(16) 0.30569(9) 0.0179(3) Uani 1 d . . .
C2 C 0.47892(17) 0.33869(16) 0.30535(9) 0.0170(3) Uani 1 d . . .
H2 H 0.5865 0.3330 0.2800 0.020 Uiso 1 calc R . .
C3 C 0.46166(17) 0.20487(16) 0.34307(9) 0.0174(3) Uani 1 d . . .
C4 C 0.30615(17) 0.21003(17) 0.38023(9) 0.0192(3) Uani 1 d . . .
H4 H 0.2974 0.1178 0.4058 0.023 Uiso 1 calc R . .
C5 C 0.16223(16) 0.35220(17) 0.37968(9) 0.0183(3) Uani 1 d . . .
C6 C 0.17898(17) 0.48619(17) 0.34238(9) 0.0190(3) Uani 1 d . . .
H6 H 0.0815 0.5832 0.3421 0.023 Uiso 1 calc R . .
C7 C 0.48955(17) 0.62607(17) 0.23327(10) 0.0206(3) Uani 1 d . . .
H7A H 0.5437 0.5495 0.1820 0.025 Uiso 1 calc R . .
H7B H 0.5672 0.5982 0.2764 0.025 Uiso 1 calc R . .
C8 C 0.44658(17) 0.79605(17) 0.20526(10) 0.0218(3) Uani 1 d . . .
H8A H 0.3979 0.8697 0.2579 0.026 Uiso 1 calc R . .
H8B H 0.3600 0.8249 0.1670 0.026 Uiso 1 calc R . .
C9 C 0.59832(17) 0.81961(17) 0.15630(10) 0.0217(3) Uani 1 d . . .
H9A H 0.6824 0.7968 0.1956 0.026 Uiso 1 calc R . .
H9B H 0.6507 0.7422 0.1053 0.026 Uiso 1 calc R . .
C10 C 0.55106(17) 0.98916(16) 0.12441(10) 0.0208(3) Uani 1 d . . .
H10A H 0.4975 1.0660 0.1756 0.025 Uiso 1 calc R . .
H10B H 0.4670 1.0113 0.0852 0.025 Uiso 1 calc R . .
C11 C 0.69957(18) 1.01789(17) 0.07553(10) 0.0217(3) Uani 1 d . . .
H11A H 0.7524 0.9421 0.0239 0.026 Uiso 1 calc R . .
H11B H 0.7842 0.9950 0.1145 0.026 Uiso 1 calc R . .
C12 C 0.65062(17) 1.18841(16) 0.04487(10) 0.0213(3) Uani 1 d . . .
H12A H 0.6025 1.2638 0.0968 0.026 Uiso 1 calc R . .
H12B H 0.5620 1.2130 0.0082 0.026 Uiso 1 calc R . .
C13 C 0.79774(17) 1.21602(16) -0.00786(10) 0.0207(3) Uani 1 d . . .
H13A H 0.8873 1.1890 0.0284 0.025 Uiso 1 calc R . .
H13B H 0.8442 1.1420 -0.0604 0.025 Uiso 1 calc R . .
C14 C 0.75070(17) 1.38713(16) -0.03720(10) 0.0202(3) Uani 1 d . . .
H14A H 0.6619 1.4141 -0.0739 0.024 Uiso 1 calc R . .
H14B H 0.7037 1.4614 0.0152 0.024 Uiso 1 calc R . .
C15 C 0.89888(17) 1.41269(17) -0.08907(10) 0.0213(3) Uani 1 d . . .
H15A H 0.9899 1.3799 -0.0534 0.026 Uiso 1 calc R . .
H15B H 0.9421 1.3420 -0.1429 0.026 Uiso 1 calc R . .
C16 C 0.85698(17) 1.58477(17) -0.11517(10) 0.0207(3) Uani 1 d . . .
H16A H 0.8124 1.6560 -0.0616 0.025 Uiso 1 calc R . .
H16B H 0.7676 1.6173 -0.1519 0.025 Uiso 1 calc R . .
C17 C 1.00801(18) 1.60759(18) -0.16566(10) 0.0237(3) Uani 1 d . . .
H17A H 1.0974 1.5749 -0.1290 0.028 Uiso 1 calc R . .
H17B H 1.0526 1.5363 -0.2192 0.028 Uiso 1 calc R . .
C18 C 0.9668(2) 1.77952(18) -0.19189(11) 0.0289(4) Uani 1 d . . .
H18A H 0.8825 1.8110 -0.2308 0.043 Uiso 1 calc R . .
H18B H 1.0690 1.7871 -0.2226 0.043 Uiso 1 calc R . .
H18C H 0.9222 1.8511 -0.1392 0.043 Uiso 1 calc R . .
C19 C 0.61225(17) 0.05195(17) 0.34613(10) 0.0208(3) Uani 1 d . . .
C20 C 0.91143(17) -0.07850(17) 0.30826(10) 0.0250(4) Uani 1 d . . .
H20A H 0.9947 -0.0840 0.2559 0.030 Uiso 1 calc R . .
H20B H 0.8921 -0.1774 0.3078 0.030 Uiso 1 calc R . .
C21 C 0.97888(19) -0.06764(19) 0.38993(11) 0.0323(4) Uani 1 d . . .
H21A H 0.9878 0.0351 0.3930 0.048 Uiso 1 calc R . .
H21B H 1.0902 -0.1557 0.3883 0.048 Uiso 1 calc R . .
H21C H 0.9025 -0.0752 0.4416 0.048 Uiso 1 calc R . .
C22 C -0.00476(17) 0.36848(17) 0.41562(9) 0.0196(3) Uani 1 d . . .
C23 C -0.15003(17) 0.39929(16) 0.44145(9) 0.0195(3) Uani 1 d . . .
C24 C -0.32662(17) 0.44859(17) 0.47124(9) 0.0176(3) Uani 1 d . . .
C25 C -0.43730(17) 0.60748(17) 0.46264(9) 0.0187(3) Uani 1 d . . .
H25 H -0.3946 0.6812 0.4372 0.022 Uiso 1 calc R . .
C26 C -0.39223(17) 0.34154(17) 0.50932(9) 0.0190(3) Uani 1 d . . .
H26 H -0.3186 0.2332 0.5158 0.023 Uiso 1 calc R . .
O1 O 0.33281(12) 0.62086(12) 0.27203(7) 0.0228(3) Uani 1 d . . .
O2 O 0.75434(12) 0.06080(12) 0.30516(7) 0.0239(3) Uani 1 d . . .
O3 O 0.60825(13) -0.06645(13) 0.37966(8) 0.0339(3) Uani 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 0.0191(7) 0.0171(7) 0.0178(7) 0.0026(5) -0.0025(6) -0.0083(6)
C2 0.0153(7) 0.0207(7) 0.0153(7) 0.0017(5) -0.0003(5) -0.0086(6)
C3 0.0165(7) 0.0171(7) 0.0183(7) -0.0005(5) -0.0031(5) -0.0064(6)
C4 0.0183(7) 0.0193(7) 0.0213(8) 0.0020(6) -0.0017(6) -0.0098(6)
C5 0.0145(7) 0.0220(7) 0.0188(7) -0.0011(6) -0.0012(6) -0.0085(6)
C6 0.0149(7) 0.0174(7) 0.0230(8) 0.0007(6) -0.0030(6) -0.0050(6)
C7 0.0165(7) 0.0206(7) 0.0236(8) 0.0039(6) -0.0008(6) -0.0078(6)
C8 0.0207(7) 0.0175(7) 0.0262(8) 0.0056(6) -0.0021(6) -0.0079(6)
C9 0.0211(7) 0.0191(7) 0.0252(8) 0.0042(6) -0.0032(6) -0.0089(6)
C10 0.0216(7) 0.0179(7) 0.0236(8) 0.0039(6) -0.0034(6) -0.0091(6)
C11 0.0210(7) 0.0194(7) 0.0252(8) 0.0059(6) -0.0037(6) -0.0093(6)
C12 0.0224(7) 0.0183(7) 0.0241(8) 0.0039(6) -0.0023(6) -0.0099(6)
C13 0.0190(7) 0.0189(7) 0.0249(8) 0.0052(6) -0.0023(6) -0.0092(6)
C14 0.0193(7) 0.0182(7) 0.0236(8) 0.0034(6) -0.0031(6) -0.0086(6)
C15 0.0205(7) 0.0204(8) 0.0240(8) 0.0041(6) -0.0014(6) -0.0104(6)
C16 0.0222(7) 0.0193(7) 0.0216(8) 0.0036(6) -0.0036(6) -0.0100(6)
C17 0.0228(8) 0.0237(8) 0.0274(8) 0.0059(6) -0.0034(6) -0.0130(6)
C18 0.0333(9) 0.0270(8) 0.0308(9) 0.0075(7) -0.0031(7) -0.0179(7)
C19 0.0191(7) 0.0186(7) 0.0246(8) 0.0028(6) -0.0037(6) -0.0079(6)
C20 0.0155(7) 0.0171(7) 0.0343(9) 0.0033(6) -0.0010(6) 0.0001(6)
C21 0.0250(8) 0.0249(8) 0.0401(10) -0.0010(7) -0.0096(7) -0.0019(7)
C22 0.0196(7) 0.0177(7) 0.0227(8) 0.0011(6) -0.0038(6) -0.0089(6)
C23 0.0186(7) 0.0180(7) 0.0232(8) 0.0003(6) -0.0030(6) -0.0090(6)
C24 0.0151(7) 0.0213(7) 0.0182(7) 0.0002(6) -0.0012(5) -0.0098(6)
C25 0.0200(7) 0.0195(7) 0.0203(8) 0.0032(6) -0.0022(6) -0.0124(6)
C26 0.0174(7) 0.0172(7) 0.0222(8) 0.0027(6) -0.0043(6) -0.0069(6)
O1 0.0161(5) 0.0175(5) 0.0326(6) 0.0076(4) 0.0001(4) -0.0066(4)
O2 0.0140(5) 0.0180(5) 0.0342(6) 0.0058(4) -0.0020(4) -0.0023(4)
O3 0.0253(6) 0.0208(6) 0.0519(8) 0.0126(5) -0.0020(5) -0.0081(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 1.3671(16) . ?
C1 C6 1.3888(19) . ?
C1 C2 1.3931(19) . ?
C2 C3 1.3980(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3854(19) . ?
C3 C19 1.4896(19) . ?
C4 C5 1.3980(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3953(19) . ?
C5 C22 1.4398(19) . ?
C6 H6 0.9500 . ?
C7 O1 1.4391(16) . ?
C7 C8 1.5122(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5248(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5236(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5238(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5239(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5302(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5239(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5236(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5228(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5246(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 O3 1.2012(17) . ?
C19 O2 1.3466(17) . ?
C20 O2 1.4559(16) . ?
C20 C21 1.505(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.1973(19) . ?
C23 C24 1.4338(18) . ?
C24 C25 1.3973(19) . ?
C24 C26 1.4053(19) . ?
C25 C26 1.3788(19) 2_466 ?
C25 H25 0.9500 . ?
C26 C25 1.3788(19) 2_466 ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 114.89(11) . . ?
O1 C1 C2 125.28(12) . . ?
C6 C1 C2 119.83(13) . . ?
C1 C2 C3 118.71(12) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 121.72(12) . . ?
C4 C3 C19 117.75(12) . . ?
C2 C3 C19 120.51(12) . . ?
C3 C4 C5 119.36(13) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.09(12) . . ?
C6 C5 C22 117.54(12) . . ?
C4 C5 C22 123.37(13) . . ?
C1 C6 C5 121.28(12) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 C8 106.12(10) . . ?
O1 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C7 C8 C9 112.99(11) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 112.25(11) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.88(11) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.27(11) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 113.54(11) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.91(11) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.19(11) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 114.17(11) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 113.10(11) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 113.31(12) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O2 123.64(13) . . ?
O3 C19 C3 124.45(13) . . ?
O2 C19 C3 111.89(12) . . ?
O2 C20 C21 110.13(12) . . ?
O2 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O2 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C5 172.37(15) . . ?
C22 C23 C24 175.69(15) . . ?
C25 C24 C26 118.74(12) . . ?
C25 C24 C23 119.41(12) . . ?
C26 C24 C23 121.85(13) . . ?
C26 C25 C24 120.75(12) 2_466 . ?
C26 C25 H25 119.6 2_466 . ?
C24 C25 H25 119.6 . . ?
C25 C26 C24 120.51(13) 2_466 . ?
C25 C26 H26 119.7 2_466 . ?
C24 C26 H26 119.7 . . ?
C1 O1 C7 118.60(10) . . ?
C19 O2 C20 116.96(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18B O2 0.98 2.66 3.5701(18) 154.7 2_775
C25 H25 O3 0.95 2.46 3.3701(17) 159.6 1_465

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.41
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.047

data_pemu5e
_database_code_depnum_ccdc_archive 'CCDC 278014'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 O3'
_chemical_formula_weight         190.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/a

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

_cell_length_a                   8.720(5)
_cell_length_b                   12.944(9)
_cell_length_c                   8.918(5)
_cell_angle_alpha                90.00(2)
_cell_angle_beta                 100.47(4)
_cell_angle_gamma                90.00(3)
_cell_volume                     989.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      13.13
_cell_measurement_theta_max      24.69

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8017
_exptl_absorpt_correction_T_max  0.8611

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CAD4 (Enraf Nonius)'
_diffrn_measurement_method       'omega-2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 250
_diffrn_standards_interval_time  3600
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1800
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.04
_diffrn_reflns_theta_max         65.01
_reflns_number_total             1681
_reflns_number_gt                1271
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 software'
_computing_cell_refinement       'CAD4 software'
_computing_data_reduction        Helena
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON
_computing_publication_material  PLATON

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
'calc w=1/[\s^2^(Fo^2^)+(0.1145P)^2^+0.1021P] 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         1681
_refine_ls_number_parameters     132
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.004
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5131(2) 0.36373(12) 0.7412(2) 0.0756(6) Uani 1 d . . .
H1 H 0.4504 0.3977 0.6812 0.113 Uiso 1 calc R . .
O2 O 0.1862(2) -0.01306(12) 0.4517(2) 0.0670(6) Uani 1 d . . .
O3 O 0.13420(18) 0.15206(12) 0.38720(18) 0.0619(5) Uani 1 d . . .
C1 C 0.4840(2) 0.26129(17) 0.7161(2) 0.0536(6) Uani 1 d . . .
C2 C 0.3649(3) 0.22543(16) 0.6049(2) 0.0513(6) Uani 1 d . . .
H2 H 0.3002 0.2714 0.5429 0.062 Uiso 1 calc R . .
C3 C 0.3431(2) 0.11920(16) 0.5869(2) 0.0489(6) Uani 1 d . . .
C4 C 0.4369(3) 0.05023(18) 0.6782(3) 0.0535(6) Uani 1 d . . .
H4 H 0.4209 -0.0204 0.6646 0.064 Uiso 1 calc R . .
C5 C 0.5565(3) 0.08687(18) 0.7913(3) 0.0527(6) Uani 1 d . . .
C6 C 0.5797(3) 0.19303(18) 0.8072(3) 0.0565(6) Uani 1 d . . .
H6 H 0.6608 0.2181 0.8805 0.068 Uiso 1 calc R . .
C7 C 0.2138(3) 0.07822(17) 0.4694(2) 0.0517(6) Uani 1 d . . .
C8 C 0.0051(3) 0.1221(2) 0.2688(3) 0.0651(7) Uani 1 d . . .
H8A H -0.0752 0.0880 0.3130 0.078 Uiso 1 calc R . .
H8B H 0.0404 0.0750 0.1976 0.078 Uiso 1 calc R . .
C9 C -0.0566(3) 0.2181(2) 0.1898(3) 0.0898(10) Uani 1 d . . .
H9A H -0.1427 0.2015 0.1100 0.135 Uiso 1 calc R . .
H9B H 0.0240 0.2510 0.1468 0.135 Uiso 1 calc R . .
H9C H -0.0912 0.2639 0.2614 0.135 Uiso 1 calc R . .
C10 C 0.6551(3) 0.01760(19) 0.8943(3) 0.0616(7) Uani 1 d . . .
C11 C 0.7356(4) -0.0329(2) 0.9826(4) 0.0784(9) Uani 1 d D . .
H11 H 0.804(3) -0.069(3) 1.056(3) 0.121(12) Uiso 1 d 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
O1 0.0790(12) 0.0403(10) 0.0887(13) -0.0028(8) -0.0345(10) 0.0007(8)
O2 0.0706(11) 0.0452(10) 0.0737(12) -0.0019(8) -0.0175(9) -0.0052(8)
O3 0.0637(10) 0.0489(9) 0.0619(10) 0.0032(7) -0.0186(8) -0.0017(8)
C1 0.0553(14) 0.0411(12) 0.0583(13) -0.0022(10) -0.0064(11) 0.0006(10)
C2 0.0529(13) 0.0435(12) 0.0515(12) 0.0020(10) -0.0064(10) 0.0032(10)
C3 0.0515(12) 0.0445(12) 0.0468(12) 0.0008(9) -0.0015(10) 0.0008(9)
C4 0.0567(14) 0.0440(12) 0.0556(14) 0.0019(10) -0.0009(11) 0.0019(10)
C5 0.0530(13) 0.0494(13) 0.0520(13) 0.0041(10) -0.0002(10) 0.0051(10)
C6 0.0548(13) 0.0515(13) 0.0547(14) -0.0011(10) -0.0124(11) 0.0012(11)
C7 0.0531(13) 0.0454(12) 0.0528(13) 0.0024(10) -0.0007(11) -0.0005(10)
C8 0.0608(15) 0.0649(16) 0.0591(14) 0.0007(12) -0.0168(12) -0.0036(12)
C9 0.091(2) 0.082(2) 0.0805(19) 0.0107(15) -0.0275(17) 0.0070(16)
C10 0.0647(15) 0.0526(14) 0.0602(15) 0.0029(11) -0.0083(12) 0.0012(11)
C11 0.0824(19) 0.0606(17) 0.0793(19) 0.0072(14) -0.0197(16) 0.0105(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.361(3) . ?
O1 H1 0.8200 . ?
O2 C7 1.210(3) . ?
O3 C7 1.322(3) . ?
O3 C8 1.450(3) . ?
C1 C6 1.375(3) . ?
C1 C2 1.379(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(3) . ?
C3 C7 1.490(3) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(4) . ?
C5 C10 1.449(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.480(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.157(4) . ?
C11 H11 0.929(18) . ?

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
C1 O1 H1 109.5 . . ?
C7 O3 C8 118.08(19) . . ?
O1 C1 C6 117.0(2) . . ?
O1 C1 C2 122.7(2) . . ?
C6 C1 C2 120.4(2) . . ?
C1 C2 C3 118.95(19) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 C7 118.6(2) . . ?
C2 C3 C7 120.14(19) . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 C10 119.2(2) . . ?
C4 C5 C10 121.8(2) . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O2 C7 O3 124.1(2) . . ?
O2 C7 C3 123.1(2) . . ?
O3 C7 C3 112.74(19) . . ?
O3 C8 C9 106.8(2) . . ?
O3 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O3 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C5 175.9(3) . . ?
C10 C11 H11 176(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O1 0.929(18) 2.35(2) 3.271(4) 172(3) 2_647
O1 H1 O2 0.82 1.91 2.727(3) 175.2 2_556

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        65.01
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.078