# Electronic Supplementary material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jubaraj Baruah'
_publ_contact_author_email       JUBA@IITG.ERNET.IN

_publ_section_title              
;
Crystal packing in some flexible carboxylic acids and
esters attached to naphthalene ring
;
loop_
_publ_author_name
'Jubaraj Baruah'
'Anirban Karmakar'
'Pallab Mondal'
'W Marjit Singh'

# Attachment '13diacid-c.cif'

data_13diacid
_database_code_depnum_ccdc_archive 'CCDC 677172'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.0505(6)
_cell_length_b                   5.1175(2)
_cell_length_c                   18.2405(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.243(2)
_cell_angle_gamma                90.00
_cell_volume                     1214.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6530
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            16164
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         26.49
_reflns_number_total             2498
_reflns_number_gt                2141
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0463P)²+0.4062P] where P=(Fo²+2Fc²)/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         2498
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.27645(10) 0.1017(3) 0.16489(7) 0.0309(3) Uani 1 1 d . . .
H8 H 0.3448 0.1031 0.1835 0.037 Uiso 1 1 calc R . .
C5 C 0.07047(10) 0.1063(3) 0.10856(7) 0.0314(3) Uani 1 1 d . . .
C10 C 0.10326(10) -0.0770(2) 0.16346(7) 0.0288(3) Uani 1 1 d . . .
C9 C 0.20846(10) -0.0715(2) 0.19126(7) 0.0291(3) Uani 1 1 d . . .
C13 C 0.29040(10) 0.6186(3) 0.02953(7) 0.0340(3) Uani 1 1 d . . .
H13A H 0.2340 0.7286 0.0424 0.041 Uiso 1 1 calc R . .
H13B H 0.2690 0.5235 -0.0150 0.041 Uiso 1 1 calc R . .
C7 C 0.24148(10) 0.2791(3) 0.10890(7) 0.0308(3) Uani 1 1 d . . .
C12 C 0.37936(11) -0.0922(3) 0.32321(7) 0.0349(3) Uani 1 1 d . . .
C6 C 0.14214(10) 0.2842(3) 0.08109(7) 0.0340(3) Uani 1 1 d . . .
H6 H 0.1211 0.4030 0.0444 0.041 Uiso 1 1 calc R . .
C14 C 0.38346(10) 0.7826(3) 0.01780(7) 0.0330(3) Uani 1 1 d . . .
C3 C -0.10198(11) -0.0689(3) 0.10845(8) 0.0440(4) Uani 1 1 d . . .
H3 H -0.1708 -0.0640 0.0911 0.053 Uiso 1 1 calc R . .
C1 C 0.03182(11) -0.2588(3) 0.18830(8) 0.0361(3) Uani 1 1 d . . .
H1 H 0.0533 -0.3822 0.2236 0.043 Uiso 1 1 calc R . .
C11 C 0.33658(11) -0.2932(3) 0.26872(8) 0.0377(3) Uani 1 1 d . . .
H11A H 0.3768 -0.2908 0.2261 0.045 Uiso 1 1 calc R . .
H11B H 0.3438 -0.4650 0.2909 0.045 Uiso 1 1 calc R . .
C4 C -0.03424(11) 0.1064(3) 0.08249(8) 0.0416(4) Uani 1 1 d . . .
H4 H -0.0575 0.2276 0.0471 0.050 Uiso 1 1 calc R . .
C2 C -0.06861(11) -0.2547(3) 0.16083(8) 0.0418(4) Uani 1 1 d . . .
H2 H -0.1148 -0.3763 0.1771 0.050 Uiso 1 1 calc R . .
O4 O 0.31807(7) 0.4427(2) 0.08719(5) 0.0386(3) Uani 1 1 d . . .
O5 O 0.36392(8) 0.9577(2) -0.03352(6) 0.0457(3) Uani 1 1 d . . .
H5O H 0.4160 1.0427 -0.0391 0.069 Uiso 1 1 calc R . .
O6 O 0.46610(8) 0.7548(2) 0.05205(6) 0.0466(3) Uani 1 1 d . . .
O1 O 0.23236(7) -0.2518(2) 0.24536(5) 0.0391(3) Uani 1 1 d . . .
O2 O 0.33174(9) 0.0764(2) 0.35089(6) 0.0523(3) Uani 1 1 d . . .
O3 O 0.47934(8) -0.1335(3) 0.33803(7) 0.0542(3) Uani 1 1 d . . .
H3O H 0.5020 -0.0282 0.3690 0.081 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 C9 1.3667(18) . ?
C8 C7 1.4165(18) . ?
C5 C4 1.4133(19) . ?
C5 C10 1.4149(18) . ?
C5 C6 1.4229(18) . ?
C10 C1 1.4153(18) . ?
C10 C9 1.4281(18) . ?
C9 O1 1.3697(15) . ?
C13 O4 1.4108(16) . ?
C13 C14 1.5045(18) . ?
C7 C6 1.3570(18) . ?
C7 O4 1.3841(15) . ?
C12 O2 1.1967(17) . ?
C12 O3 1.3297(17) . ?
C12 C11 1.508(2) . ?
C14 O6 1.2142(16) . ?
C14 O5 1.3075(16) . ?
C3 C4 1.368(2) . ?
C3 C2 1.395(2) . ?
C1 C2 1.368(2) . ?
C11 O1 1.4108(17) . ?

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
C9 C8 C7 119.11(12) . . ?
C4 C5 C10 118.21(12) . . ?
C4 C5 C6 121.72(13) . . ?
C10 C5 C6 120.07(12) . . ?
C5 C10 C1 119.37(12) . . ?
C5 C10 C9 118.10(11) . . ?
C1 C10 C9 122.53(12) . . ?
C8 C9 O1 124.83(12) . . ?
C8 C9 C10 121.31(11) . . ?
O1 C9 C10 113.86(11) . . ?
O4 C13 C14 107.28(10) . . ?
C6 C7 O4 124.85(12) . . ?
C6 C7 C8 122.00(12) . . ?
O4 C7 C8 113.14(11) . . ?
O2 C12 O3 124.15(14) . . ?
O2 C12 C11 126.24(13) . . ?
O3 C12 C11 109.59(12) . . ?
C7 C6 C5 119.39(12) . . ?
O6 C14 O5 124.57(12) . . ?
O6 C14 C13 123.86(12) . . ?
O5 C14 C13 111.57(11) . . ?
C4 C3 C2 120.47(13) . . ?
C2 C1 C10 120.57(13) . . ?
O1 C11 C12 113.47(12) . . ?
C3 C4 C5 121.11(14) . . ?
C1 C2 C3 120.22(13) . . ?
C7 O4 C13 116.67(10) . . ?
C9 O1 C11 118.80(10) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044

# Attachment '15diester2-c.cif'

data_15diester2
_database_code_depnum_ccdc_archive 'CCDC 677173'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29

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                   7.0661(4)
_cell_length_b                   7.4816(5)
_cell_length_c                   8.0748(5)
_cell_angle_alpha                67.837(4)
_cell_angle_beta                 72.069(4)
_cell_angle_gamma                74.951(4)
_cell_volume                     371.12(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1652
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      28.03

_exptl_crystal_description       Blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            2773
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1315
_reflns_number_gt                1124
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.1063P)²+0.0362P] where P=(Fo²+2Fc²)/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         1315
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.40816(18) 0.55445(19) 0.19966(15) 0.0558(4) Uani 1 1 d . . .
O3 O 0.2885(2) 0.64505(19) 0.45110(16) 0.0648(5) Uani 1 1 d . . .
O1 O 0.15586(17) 0.30042(16) 0.64570(14) 0.0479(4) Uani 1 1 d . . .
C7 C 0.3162(2) 0.5287(2) 0.3752(2) 0.0433(4) Uani 1 1 d . . .
C6 C 0.2582(3) 0.3282(2) 0.4594(2) 0.0472(5) Uani 1 1 d . . .
H6A H 0.1714 0.3155 0.3932 0.057 Uiso 1 1 calc R . .
H6B H 0.3779 0.2297 0.4517 0.057 Uiso 1 1 calc R . .
C4 C 0.1149(2) 0.1154(2) 0.7507(2) 0.0401(4) Uani 1 1 d . . .
C3 C 0.1558(2) -0.0391(2) 0.6863(2) 0.0480(5) Uani 1 1 d . . .
H3 H 0.2138 -0.0225 0.5624 0.058 Uiso 1 1 calc R . .
C2 C 0.1096(2) -0.2226(2) 0.8082(2) 0.0494(5) Uani 1 1 d . . .
H2 H 0.1387 -0.3270 0.7636 0.059 Uiso 1 1 calc R . .
C1 C 0.0231(2) -0.2510(2) 0.9902(2) 0.0441(4) Uani 1 1 d . . .
H1 H -0.0053 -0.3739 1.0687 0.053 Uiso 1 1 calc R . .
C5 C 0.0233(2) 0.0928(2) 0.9405(2) 0.0372(4) Uani 1 1 d . . .
C8 C 0.4829(3) 0.7369(3) 0.0952(2) 0.0646(6) Uani 1 1 d . . .
H8A H 0.3740 0.8440 0.1007 0.097 Uiso 1 1 calc R . .
H8B H 0.5395 0.7419 -0.0305 0.097 Uiso 1 1 calc R . .
H8C H 0.5849 0.7461 0.1461 0.097 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.3270(18) . ?
O2 C8 1.444(2) . ?
O3 C7 1.188(2) . ?
O1 C4 1.3748(19) . ?
O1 C6 1.4144(18) . ?
C7 C6 1.503(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 C3 1.370(2) . ?
C4 C5 1.431(2) . ?
C3 C2 1.405(2) . ?
C3 H3 0.9300 . ?
C2 C1 1.363(2) . ?
C2 H2 0.9300 . ?
C1 C5 1.417(2) 2_557 ?
C1 H1 0.9300 . ?
C5 C5 1.412(3) 2_557 ?
C5 C1 1.417(2) 2_557 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C7 O2 C8 116.95(14) . . ?
C4 O1 C6 116.69(12) . . ?
O3 C7 O2 124.96(15) . . ?
O3 C7 C6 126.71(15) . . ?
O2 C7 C6 108.33(13) . . ?
O1 C6 C7 108.92(13) . . ?
O1 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
O1 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C3 C4 O1 125.03(14) . . ?
C3 C4 C5 120.75(15) . . ?
O1 C4 C5 114.22(13) . . ?
C4 C3 C2 119.74(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C1 C2 C3 121.51(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C1 C5 119.76(15) . 2_557 ?
C2 C1 H1 120.1 . . ?
C5 C1 H1 120.1 2_557 . ?
C5 C5 C1 119.97(17) 2_557 2_557 ?
C5 C5 C4 118.27(17) 2_557 . ?
C1 C5 C4 121.75(15) 2_557 . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.105

# Attachment '16diester.cif'

data_16diester
_database_code_depnum_ccdc_archive 'CCDC 677174'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29

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_H-M   P2(1)/c

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

_cell_length_a                   17.5782(2)
_cell_length_b                   9.95720(10)
_cell_length_c                   8.62060(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7140(10)
_cell_angle_gamma                90.00
_cell_volume                     1495.21(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3758
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      23.65

_exptl_crystal_description       Blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            21190
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         28.30
_reflns_number_total             3688
_reflns_number_gt                2329
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0467P)²+0.1616P] where P=(Fo²+2Fc²)/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         3688
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C10 C 0.28228(8) 0.99944(13) 0.56805(15) 0.0465(3) Uani 1 1 d . . .
C3 C 0.15735(8) 0.83261(14) 0.46527(15) 0.0490(3) Uani 1 1 d . . .
C4 C 0.15100(8) 0.92299(14) 0.58193(15) 0.0503(3) Uani 1 1 d . . .
H4 H 0.1055 0.9290 0.6256 0.060 Uiso 1 1 calc R . .
C5 C 0.21378(8) 1.00759(14) 0.63640(15) 0.0488(3) Uani 1 1 d . . .
C9 C 0.34450(9) 1.08695(14) 0.62324(16) 0.0509(4) Uani 1 1 d . . .
C2 C 0.22581(9) 0.82257(15) 0.39793(16) 0.0532(4) Uani 1 1 d . . .
H2 H 0.2297 0.7599 0.3194 0.064 Uiso 1 1 calc R . .
C1 C 0.28625(9) 0.90438(15) 0.44758(16) 0.0521(4) Uani 1 1 d . . .
H1 H 0.3310 0.8976 0.4014 0.063 Uiso 1 1 calc R . .
C12 C -0.02154(9) 0.64521(17) 0.38250(17) 0.0561(4) Uani 1 1 d . . .
C15 C 0.51675(9) 1.06715(15) 0.73958(17) 0.0547(4) Uani 1 1 d . . .
C8 C 0.33920(10) 1.17284(16) 0.74452(18) 0.0630(4) Uani 1 1 d . . .
H8 H 0.3803 1.2280 0.7816 0.076 Uiso 1 1 calc R . .
C14 C 0.47574(9) 1.14337(15) 0.60222(18) 0.0587(4) Uani 1 1 d . . .
H14A H 0.4642 1.2334 0.6351 0.070 Uiso 1 1 calc R . .
H14B H 0.5089 1.1507 0.5213 0.070 Uiso 1 1 calc R . .
C6 C 0.20938(10) 1.09941(17) 0.76099(17) 0.0635(4) Uani 1 1 d . . .
H6 H 0.1646 1.1062 0.8068 0.076 Uiso 1 1 calc R . .
C11 C 0.02913(9) 0.75405(16) 0.45999(18) 0.0591(4) Uani 1 1 d . . .
H11A H 0.0061 0.8414 0.4355 0.071 Uiso 1 1 calc R . .
H11B H 0.0359 0.7424 0.5727 0.071 Uiso 1 1 calc R . .
C7 C 0.27118(11) 1.17730(17) 0.81285(18) 0.0696(5) Uani 1 1 d . . .
H7 H 0.2682 1.2354 0.8963 0.084 Uiso 1 1 calc R . .
C13 C -0.14729(10) 0.5610(2) 0.3539(2) 0.0802(5) Uani 1 1 d . . .
H13A H -0.1475 0.5591 0.2425 0.120 Uiso 1 1 calc R . .
H13B H -0.1973 0.5862 0.3771 0.120 Uiso 1 1 calc R . .
H13C H -0.1343 0.4737 0.3965 0.120 Uiso 1 1 calc R . .
C16 C 0.62523(11) 1.0699(2) 0.9335(2) 0.0867(6) Uani 1 1 d . . .
H16A H 0.5979 1.0593 1.0219 0.130 Uiso 1 1 calc R . .
H16B H 0.6705 1.1228 0.9633 0.130 Uiso 1 1 calc R . .
H16C H 0.6396 0.9832 0.8983 0.130 Uiso 1 1 calc R . .
O1 O 0.10080(6) 0.74514(11) 0.40300(12) 0.0605(3) Uani 1 1 d . . .
O4 O 0.40632(6) 1.07763(10) 0.54027(12) 0.0587(3) Uani 1 1 d . . .
O5 O 0.57622(6) 1.13729(11) 0.80752(12) 0.0671(3) Uani 1 1 d . . .
O2 O -0.09116(6) 0.65791(12) 0.42260(13) 0.0701(3) Uani 1 1 d . . .
O6 O 0.50009(7) 0.95709(12) 0.77797(15) 0.0768(4) Uani 1 1 d . . .
O3 O -0.00272(7) 0.55948(13) 0.29922(15) 0.0824(4) Uani 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
C10 C5 1.412(2) . ?
C10 C1 1.4138(19) . ?
C10 C9 1.429(2) . ?
C3 C4 1.3653(19) . ?
C3 O1 1.3754(16) . ?
C3 C2 1.408(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.421(2) . ?
C9 C8 1.364(2) . ?
C9 O4 1.3819(18) . ?
C2 C1 1.361(2) . ?
C12 O3 1.1904(18) . ?
C12 O2 1.3216(18) . ?
C12 C11 1.501(2) . ?
C15 O6 1.1925(17) . ?
C15 O5 1.3265(17) . ?
C15 C14 1.506(2) . ?
C8 C7 1.403(2) . ?
C14 O4 1.4241(17) . ?
C6 C7 1.360(2) . ?
C11 O1 1.4152(17) . ?
C13 O2 1.448(2) . ?
C16 O5 1.4561(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C10 C1 118.29(13) . . ?
C5 C10 C9 118.91(13) . . ?
C1 C10 C9 122.80(14) . . ?
C4 C3 O1 125.36(13) . . ?
C4 C3 C2 120.62(13) . . ?
O1 C3 C2 114.02(12) . . ?
C3 C4 C5 119.93(13) . . ?
C10 C5 C4 119.81(12) . . ?
C10 C5 C6 119.24(14) . . ?
C4 C5 C6 120.94(14) . . ?
C8 C9 O4 125.34(14) . . ?
C8 C9 C10 120.64(15) . . ?
O4 C9 C10 113.99(12) . . ?
C1 C2 C3 120.13(13) . . ?
C2 C1 C10 121.21(14) . . ?
O3 C12 O2 124.64(15) . . ?
O3 C12 C11 126.13(15) . . ?
O2 C12 C11 109.23(13) . . ?
O6 C15 O5 124.73(14) . . ?
O6 C15 C14 124.88(14) . . ?
O5 C15 C14 110.33(13) . . ?
C9 C8 C7 119.45(15) . . ?
O4 C14 C15 111.02(12) . . ?
C7 C6 C5 119.56(16) . . ?
O1 C11 C12 107.63(12) . . ?
C6 C7 C8 122.14(15) . . ?
C3 O1 C11 117.08(11) . . ?
C9 O4 C14 117.96(12) . . ?
C15 O5 C16 116.04(13) . . ?
C12 O2 C13 115.67(13) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.029
# Attachment '27dicarboxydmso_0m.cif'

data_27dicarboxydmso_0m
_database_code_depnum_ccdc_archive 'CCDC 677175'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.95750(10)
_cell_length_b                   6.92300(10)
_cell_length_c                   23.3344(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.6670(10)
_cell_angle_gamma                90.00
_cell_volume                     1224.86(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3117
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.91

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            15934
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         28.32
_reflns_number_total             3027
_reflns_number_gt                1975
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0650P)²+0.1707P] where P=(Fo²+2Fc²)/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         3027
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O3 O 0.10929(13) 0.20323(16) 0.02607(4) 0.0442(3) Uani 1 1 d . . .
O2 O 0.20649(15) -0.10067(16) 0.04445(5) 0.0541(4) Uani 1 1 d . . .
H2O H 0.1123 -0.1262 0.0192 0.081 Uiso 1 1 calc R . .
O1 O 0.39584(13) 0.34374(15) 0.10361(4) 0.0425(3) Uani 1 1 d . . .
O6 O 1.41464(13) 0.20624(16) 0.46527(4) 0.0424(3) Uani 1 1 d . . .
O5 O 1.28757(14) -0.08613(16) 0.45598(5) 0.0489(3) Uani 1 1 d . . .
H5O H 1.3772 -0.1150 0.4830 0.073 Uiso 1 1 calc R . .
O4 O 1.13283(13) 0.35496(15) 0.38449(4) 0.0443(3) Uani 1 1 d . . .
C12 C 0.22144(18) 0.0852(2) 0.05144(6) 0.0354(4) Uani 1 1 d . . .
C11 C 0.39377(19) 0.1411(2) 0.09677(6) 0.0393(4) Uani 1 1 d . . .
H11A H 0.4052 0.0788 0.1350 0.047 Uiso 1 1 calc R . .
H11B H 0.4915 0.1004 0.0829 0.047 Uiso 1 1 calc R . .
C2 C 0.51250(18) 0.4232(2) 0.15392(6) 0.0335(3) Uani 1 1 d . . .
C3 C 0.48322(19) 0.6211(2) 0.16093(6) 0.0389(4) Uani 1 1 d . . .
H3 H 0.3910 0.6844 0.1330 0.047 Uiso 1 1 calc R . .
C4 C 0.58984(19) 0.7198(2) 0.20862(6) 0.0371(4) Uani 1 1 d . . .
H4 H 0.5703 0.8508 0.2127 0.045 Uiso 1 1 calc R . .
C5 C 0.73031(17) 0.6263(2) 0.25218(5) 0.0312(3) Uani 1 1 d . . .
C6 C 0.84393(19) 0.7259(2) 0.30212(6) 0.0363(4) Uani 1 1 d . . .
H6 H 0.8280 0.8577 0.3063 0.044 Uiso 1 1 calc R . .
C7 C 0.97587(19) 0.6324(2) 0.34404(6) 0.0359(4) Uani 1 1 d . . .
H7 H 1.0501 0.7002 0.3763 0.043 Uiso 1 1 calc R . .
C8 C 0.99927(18) 0.4327(2) 0.33834(6) 0.0332(3) Uani 1 1 d . . .
C9 C 0.89453(18) 0.3308(2) 0.29013(6) 0.0344(4) Uani 1 1 d . . .
H9 H 0.9129 0.1992 0.2867 0.041 Uiso 1 1 calc R . .
C10 C 0.75798(16) 0.4272(2) 0.24550(5) 0.0291(3) Uani 1 1 d . . .
C1 C 0.64730(18) 0.3264(2) 0.19483(6) 0.0328(3) Uani 1 1 d . . .
H1 H 0.6661 0.1959 0.1895 0.039 Uiso 1 1 calc R . .
C13 C 1.13387(19) 0.1527(2) 0.39162(6) 0.0374(4) Uani 1 1 d . . .
H13A H 1.1363 0.0901 0.3547 0.045 Uiso 1 1 calc R . .
H13B H 1.0279 0.1119 0.4005 0.045 Uiso 1 1 calc R . .
C14 C 1.29411(19) 0.0955(2) 0.44225(6) 0.0349(4) Uani 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
O3 C12 1.2225(17) . ?
O2 C12 1.2977(18) . ?
O2 H2O 0.8200 . ?
O1 C2 1.3716(15) . ?
O1 C11 1.4116(18) . ?
O6 C14 1.2178(17) . ?
O5 C14 1.3028(18) . ?
O5 H5O 0.8200 . ?
O4 C8 1.3726(15) . ?
O4 C13 1.4101(18) . ?
C12 C11 1.5063(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 C1 1.3748(18) . ?
C2 C3 1.408(2) . ?
C3 C4 1.3609(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.4184(18) . ?
C4 H4 0.9300 . ?
C5 C10 1.412(2) . ?
C5 C6 1.4182(18) . ?
C6 C7 1.3620(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.3745(18) . ?
C9 C10 1.4227(17) . ?
C9 H9 0.9300 . ?
C10 C1 1.4244(17) . ?
C1 H1 0.9300 . ?
C13 C14 1.5046(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C12 O2 H2O 109.5 . . ?
C2 O1 C11 118.50(11) . . ?
C14 O5 H5O 109.5 . . ?
C8 O4 C13 117.23(11) . . ?
O3 C12 O2 125.20(13) . . ?
O3 C12 C11 122.92(14) . . ?
O2 C12 C11 111.86(12) . . ?
O1 C11 C12 108.17(12) . . ?
O1 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O1 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O1 C2 C1 125.54(14) . . ?
O1 C2 C3 113.39(12) . . ?
C1 C2 C3 121.07(13) . . ?
C4 C3 C2 119.97(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.14(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C10 C5 C6 118.92(12) . . ?
C10 C5 C4 118.79(12) . . ?
C6 C5 C4 122.29(14) . . ?
C7 C6 C5 121.28(14) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.64(13) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
O4 C8 C9 124.99(13) . . ?
O4 C8 C7 113.86(12) . . ?
C9 C8 C7 121.15(13) . . ?
C8 C9 C10 119.80(14) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C5 C10 C9 119.16(12) . . ?
C5 C10 C1 119.49(12) . . ?
C9 C10 C1 121.34(14) . . ?
C2 C1 C10 119.52(14) . . ?
C2 C1 H1 120.2 . . ?
C10 C1 H1 120.2 . . ?
O4 C13 C14 109.09(12) . . ?
O4 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
O4 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O6 C14 O5 125.73(13) . . ?
O6 C14 C13 123.17(14) . . ?
O5 C14 C13 111.06(12) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046
# Attachment 'tgadiol_0m-c.cif'

data_tgadiol_0m
_database_code_depnum_ccdc_archive 'CCDC 679649'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O6 S2'
_chemical_formula_weight         340.36

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   5.5518(4)
_cell_length_b                   19.8748(14)
_cell_length_c                   39.870(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4399.3(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2619
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            46463
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.02
_diffrn_reflns_theta_max         25.49
_reflns_number_total             4037
_reflns_number_gt                2819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0717P)²+2.8005P] where P=(Fo²+2Fc²)/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         4037
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
O1 O 0.6567(5) 0.18523(14) 0.04764(8) 0.0643(8) Uani 1 1 d . . .
H1O H 0.6807 0.2259 0.0484 0.096 Uiso 1 1 calc R . .
S2 S 0.39827(18) 0.06074(5) 0.02905(3) 0.0503(3) Uani 1 1 d . . .
S1 S -0.07958(16) 0.03499(5) 0.07639(2) 0.0450(3) Uani 1 1 d . . .
S3 S 0.72006(18) 1.05863(5) 0.22219(2) 0.0469(3) Uani 1 1 d . . .
C6 C 0.0930(7) 0.13894(18) 0.11319(10) 0.0439(9) Uani 1 1 d . . .
C7 C 0.1320(6) 0.09874(17) 0.08592(9) 0.0389(8) Uani 1 1 d . . .
C14 C 0.2437(7) -0.06902(18) 0.08558(10) 0.0449(9) Uani 1 1 d . . .
C10 C 0.4400(7) 0.20919(18) 0.09813(10) 0.0467(10) Uani 1 1 d . . .
C5 C 0.2452(7) 0.19521(18) 0.12020(10) 0.0466(9) Uani 1 1 d . . .
C8 C 0.3259(6) 0.11383(18) 0.06328(9) 0.0408(8) Uani 1 1 d . . .
C9 C 0.4721(7) 0.16835(19) 0.06959(10) 0.0462(9) Uani 1 1 d . . .
C13 C 0.0219(7) -0.03843(19) 0.09980(10) 0.0469(9) Uani 1 1 d . . .
H13A H 0.0526 -0.0254 0.1229 0.056 Uiso 1 1 calc R . .
H13B H -0.1054 -0.0719 0.0999 0.056 Uiso 1 1 calc R . .
C1 C 0.5966(8) 0.2636(2) 0.10617(12) 0.0631(12) Uani 1 1 d . . .
H1A H 0.7267 0.2735 0.0923 0.076 Uiso 1 1 calc R . .
C11 C 0.1759(7) 0.0840(2) -0.00176(10) 0.0519(10) Uani 1 1 d . . .
H11A H 0.1753 0.0510 -0.0197 0.062 Uiso 1 1 calc R . .
H11B H 0.0177 0.0840 0.0086 0.062 Uiso 1 1 calc R . .
C4 C 0.2067(8) 0.2367(2) 0.14861(11) 0.0604(11) Uani 1 1 d . . .
H4 H 0.0782 0.2281 0.1629 0.072 Uiso 1 1 calc R . .
C3 C 0.3589(10) 0.2894(2) 0.15495(12) 0.0704(14) Uani 1 1 d . . .
H3 H 0.3301 0.3173 0.1732 0.084 Uiso 1 1 calc R . .
C12 C 0.2266(9) 0.1531(2) -0.01633(11) 0.0610(12) Uani 1 1 d . . .
C2 C 0.5551(10) 0.3015(2) 0.13439(14) 0.0717(15) Uani 1 1 d . . .
H2 H 0.6611 0.3361 0.1398 0.086 Uiso 1 1 calc R . .
O5 O 0.4443(5) -0.05976(15) 0.09680(8) 0.0637(8) Uani 1 1 d . . .
O6 O 0.2060(5) -0.10679(15) 0.05904(8) 0.0615(8) Uani 1 1 d . . .
H6O H 0.3297 -0.1273 0.0544 0.092 Uiso 1 1 calc R . .
O3 O 0.0634(6) 0.19654(16) -0.00883(9) 0.0803(10) Uani 1 1 d . . .
H3O H 0.0980 0.2330 -0.0172 0.120 Uiso 1 1 calc R . .
O4 O 0.3999(7) 0.16618(18) -0.03310(9) 0.0840(11) Uani 1 1 d . . .
O2 O -0.0864(5) 0.12886(14) 0.13578(7) 0.0573(7) Uani 1 1 d . . .
H2O H -0.1591 0.0942 0.1311 0.086 Uiso 1 1 calc R . .
C19 C 0.5977(6) 0.98305(16) 0.23813(8) 0.0372(8) Uani 1 1 d . . .
C18 C 0.6931(7) 0.92348(18) 0.22739(9) 0.0434(9) Uani 1 1 d . . .
C17 C 0.5987(7) 0.86105(18) 0.23883(9) 0.0450(9) Uani 1 1 d . . .
C16 C 0.6949(9) 0.7988(2) 0.22862(12) 0.0692(14) Uani 1 1 d . . .
H16 H 0.8271 0.7980 0.2143 0.083 Uiso 1 1 calc R . .
C15 C 0.5975(11) 0.7401(2) 0.23937(14) 0.0908(19) Uani 1 1 d . . .
H15 H 0.6631 0.6994 0.2323 0.109 Uiso 1 1 calc R . .
O7 O 0.8772(5) 0.91773(14) 0.20480(8) 0.0639(8) Uani 1 1 d . . .
H7O H 0.9321 0.9551 0.2007 0.096 Uiso 1 1 calc R . .
C21 C 0.4062(7) 1.0347(2) 0.17044(10) 0.0497(10) Uani 1 1 d . . .
C20 C 0.4778(8) 1.0877(2) 0.19491(10) 0.0532(10) Uani 1 1 d . . .
H20A H 0.3395 1.0999 0.2085 0.064 Uiso 1 1 calc R . .
H20B H 0.5303 1.1274 0.1828 0.064 Uiso 1 1 calc R . .
O9 O 0.5549(5) 1.02975(17) 0.14445(7) 0.0658(9) Uani 1 1 d . . .
H9O H 0.5075 1.0001 0.1318 0.099 Uiso 1 1 calc R . .
O8 O 0.2365(6) 0.99829(17) 0.17369(8) 0.0729(9) Uani 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
O1 C9 1.389(4) . ?
S2 C8 1.771(4) . ?
S2 C11 1.802(4) . ?
S1 C7 1.769(3) . ?
S1 C13 1.822(4) . ?
S3 C19 1.767(3) . ?
S3 C20 1.823(4) . ?
C6 O2 1.358(4) . ?
C6 C7 1.367(5) . ?
C6 C5 1.429(5) . ?
C7 C8 1.437(5) . ?
C14 O5 1.214(4) . ?
C14 O6 1.314(4) . ?
C14 C13 1.486(5) . ?
C10 C9 1.409(5) . ?
C10 C5 1.422(5) . ?
C10 C1 1.424(5) . ?
C5 C4 1.417(6) . ?
C8 C9 1.377(5) . ?
C1 C2 1.374(7) . ?
C11 C12 1.517(6) . ?
C4 C3 1.369(6) . ?
C3 C2 1.385(7) . ?
C12 O4 1.200(5) . ?
C12 O3 1.287(5) . ?
C19 C18 1.366(5) . ?
C19 C19 1.440(7) 3_655 ?
C18 O7 1.367(4) . ?
C18 C17 1.422(5) . ?
C17 C16 1.407(5) . ?
C17 C17 1.412(7) 3_655 ?
C16 C15 1.356(6) . ?
C15 C15 1.375(10) 3_655 ?
C21 O8 1.195(5) . ?
C21 O9 1.328(5) . ?
C21 C20 1.489(6) . ?

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
C8 S2 C11 102.54(18) . . ?
C7 S1 C13 104.96(17) . . ?
C19 S3 C20 101.53(18) . . ?
O2 C6 C7 123.9(3) . . ?
O2 C6 C5 114.8(3) . . ?
C7 C6 C5 121.3(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 S1 119.0(3) . . ?
C8 C7 S1 120.8(3) . . ?
O5 C14 O6 122.0(4) . . ?
O5 C14 C13 123.9(4) . . ?
O6 C14 C13 114.1(3) . . ?
C9 C10 C5 118.9(3) . . ?
C9 C10 C1 122.8(4) . . ?
C5 C10 C1 118.3(4) . . ?
C4 C5 C10 119.7(4) . . ?
C4 C5 C6 121.5(4) . . ?
C10 C5 C6 118.8(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 S2 118.4(3) . . ?
C7 C8 S2 122.0(3) . . ?
C8 C9 O1 120.6(4) . . ?
C8 C9 C10 121.8(4) . . ?
O1 C9 C10 117.6(3) . . ?
C14 C13 S1 112.9(3) . . ?
C2 C1 C10 119.9(5) . . ?
C12 C11 S2 111.5(3) . . ?
C3 C4 C5 120.0(4) . . ?
C4 C3 C2 120.6(4) . . ?
O4 C12 O3 123.3(5) . . ?
O4 C12 C11 123.9(4) . . ?
O3 C12 C11 112.8(4) . . ?
C1 C2 C3 121.4(4) . . ?
C18 C19 C19 119.9(2) . 3_655 ?
C18 C19 S3 118.4(3) . . ?
C19 C19 S3 121.74(12) 3_655 . ?
C19 C18 O7 124.7(3) . . ?
C19 C18 C17 120.9(3) . . ?
O7 C18 C17 114.5(3) . . ?
C16 C17 C17 118.5(2) . 3_655 ?
C16 C17 C18 122.3(4) . . ?
C17 C17 C18 119.2(2) 3_655 . ?
C15 C16 C17 120.9(4) . . ?
C16 C15 C15 120.6(3) . 3_655 ?
O8 C21 O9 122.0(4) . . ?
O8 C21 C20 124.6(4) . . ?
O9 C21 C20 113.4(3) . . ?
C21 C20 S3 111.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.096


# Attachment '13diester_2.cif'

data_13diester_2
_database_code_depnum_ccdc_archive 'CCDC 684223'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29

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_H-M   Cmca

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

_cell_length_a                   6.7148(3)
_cell_length_b                   16.6214(6)
_cell_length_c                   27.1596(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3031.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3697
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            10265
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1485
_reflns_number_gt                919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0894P)²+8.2933P] 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         1485
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2404
_refine_ls_wR_factor_gt          0.1917
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0000 0.1919(2) 0.14662(12) 0.0562(11) Uani 1 2 d S . .
O2 O 0.0000 -0.0073(2) 0.10314(14) 0.0772(15) Uani 1 2 d S . .
O3 O 0.0000 0.1085(2) 0.06116(15) 0.0824(16) Uani 1 2 d S . .
O4 O 0.0000 0.2042(2) 0.32137(12) 0.0548(11) Uani 1 2 d S . .
O5 O 0.0000 0.2357(2) 0.44968(14) 0.0751(14) Uani 1 2 d S . .
O6 O 0.0000 0.1213(3) 0.40713(16) 0.0942(19) Uani 1 2 d S . .
C1 C 0.0000 0.3574(3) 0.1381(2) 0.0536(15) Uani 1 2 d S . .
H1 H 0.0000 0.3269 0.1094 0.064 Uiso 1 2 calc SR . .
C2 C 0.0000 0.4391(4) 0.1349(2) 0.0667(17) Uani 1 2 d S . .
H2 H 0.0000 0.4636 0.1041 0.080 Uiso 1 2 calc SR . .
C3 C 0.0000 0.4865(3) 0.1774(2) 0.0604(16) Uani 1 2 d S . .
H3 H 0.0000 0.5423 0.1749 0.073 Uiso 1 2 calc SR . .
C4 C 0.0000 0.4505(4) 0.2228(2) 0.0593(16) Uani 1 2 d S . .
H4 H 0.0000 0.4826 0.2508 0.071 Uiso 1 2 d SR . .
C5 C 0.0000 0.3656(3) 0.22793(18) 0.0433(13) Uani 1 2 d S . .
C6 C 0.0000 0.3288(3) 0.27508(19) 0.0498(14) Uani 1 2 d S . .
H6 H 0.0000 0.3602 0.3034 0.060 Uiso 1 2 calc SR . .
C7 C 0.0000 0.2475(3) 0.27826(17) 0.0422(12) Uani 1 2 d S . .
C8 C 0.0000 0.1986(3) 0.23545(17) 0.0457(13) Uani 1 2 d S . .
H8 H 0.0000 0.1428 0.2382 0.055 Uiso 1 2 calc SR . .
C9 C 0.0000 0.2340(3) 0.19028(17) 0.0422(12) Uani 1 2 d S . .
C10 C 0.0000 0.3181(3) 0.18457(18) 0.0465(13) Uani 1 2 d S . .
C11 C 0.0000 0.1081(3) 0.1497(2) 0.0521(15) Uani 1 2 d S . .
C12 C 0.0000 0.0722(4) 0.0990(2) 0.0603(16) Uani 1 2 d S . .
C13 C 0.0000 -0.0498(6) 0.0569(3) 0.141(5) Uani 1 2 d S . .
C14 C 0.0000 0.2489(3) 0.3656(2) 0.0490(14) Uani 1 2 d S . .
C15 C 0.0000 0.1924(4) 0.40839(19) 0.0601(16) Uani 1 2 d S . .
C16 C 0.0000 0.1926(7) 0.4955(3) 0.116(4) Uani 1 2 d S . .
H14A H 0.112(5) 0.279(2) 0.3681(12) 0.049(10) Uiso 1 1 d . . .
H11A H -0.112(6) 0.088(2) 0.1659(14) 0.060(12) Uiso 1 1 d . . .
H16A H 0.0000 0.236(4) 0.524(3) 0.09(2) Uiso 1 2 d S . .
H17A H 0.071(9) 0.144(4) 0.495(2) 0.13(3) Uiso 1 1 d . . .
H13A H 0.057(9) -0.104(3) 0.0607(17) 0.12(2) Uiso 1 1 d . . .
H13B H 0.0000 -0.016(8) 0.027(4) 0.20(6) Uiso 1 2 d S . .


_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 C9 1.377(6) . ?
O1 C11 1.395(6) . ?
O2 C12 1.327(7) . ?
O2 C13 1.440(8) . ?
O3 C12 1.191(7) . ?
O4 C7 1.375(6) . ?
O4 C14 1.412(6) . ?
O5 C15 1.333(7) . ?
O5 C16 1.435(9) . ?
O6 C15 1.182(7) . ?
C1 C2 1.359(8) . ?
C1 C10 1.422(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(8) . ?
C4 H4 0.9300 . ?
C5 C10 1.418(7) . ?
C5 C6 1.419(7) . ?
C6 C7 1.354(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(7) . ?
C8 C9 1.361(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(7) . ?
C11 C12 1.500(8) . ?
C11 H11A 0.94(4) . ?
C13 H13A 0.99(5) . ?
C13 H13B 0.99(10) . ?
C14 C15 1.495(8) . ?
C14 H14A 0.90(4) . ?
C16 H16A 1.06(7) . ?
C16 H17A 0.93(6) . ?

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
C9 O1 C11 117.1(4) . . ?
C12 O2 C13 114.5(5) . . ?
C7 O4 C14 116.6(4) . . ?
C15 O5 C16 117.3(6) . . ?
C2 C1 C10 121.0(5) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C1 C2 C3 120.7(6) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C10 118.2(5) . . ?
C4 C5 C6 121.2(5) . . ?
C10 C5 C6 120.6(5) . . ?
C7 C6 C5 119.2(5) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 O4 125.3(4) . . ?
C6 C7 C8 121.3(5) . . ?
O4 C7 C8 113.4(4) . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 O1 123.8(5) . . ?
C8 C9 C10 121.9(5) . . ?
O1 C9 C10 114.2(4) . . ?
C9 C10 C5 117.5(4) . . ?
C9 C10 C1 123.7(5) . . ?
C5 C10 C1 118.8(5) . . ?
O1 C11 C12 110.0(5) . . ?
O1 C11 H11A 113(3) . . ?
C12 C11 H11A 107(2) . . ?
O3 C12 O2 125.3(5) . . ?
O3 C12 C11 126.1(6) . . ?
O2 C12 C11 108.5(5) . . ?
O2 C13 H13A 111(3) . . ?
O2 C13 H13B 116(7) . . ?
H13A C13 H13B 127(7) . . ?
O4 C14 C15 109.3(5) . . ?
O4 C14 H14A 111(2) . . ?
C15 C14 H14A 107(2) . . ?
O6 C15 O5 124.3(5) . . ?
O6 C15 C14 127.3(5) . . ?
O5 C15 C14 108.4(5) . . ?
O5 C16 H16A 108(4) . . ?
O5 C16 H17A 114(4) . . ?
H16A C16 H17A 127(5) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060

# Attachment '16diacid-c.cif'

data_16diacid
_database_code_depnum_ccdc_archive 'CCDC 684224'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O6'
_chemical_formula_weight         276.24

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.9808(3)
_cell_length_b                   10.8072(8)
_cell_length_c                   12.2998(8)
_cell_angle_alpha                68.554(4)
_cell_angle_beta                 79.210(4)
_cell_angle_gamma                80.026(4)
_cell_volume                     601.36(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2675
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      28.02

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            6288
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2342
_reflns_number_gt                1917
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0531P)²+0.0781P] where P=(Fo²+2Fc²)/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         2342
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
C9 C 1.1043(3) 0.23713(13) 0.15606(12) 0.0336(3) Uani 1 1 d . . .
C10 C 0.9437(3) 0.12775(13) 0.21206(12) 0.0306(3) Uani 1 1 d . . .
C3 C 0.6225(3) -0.08493(13) 0.31331(12) 0.0327(3) Uani 1 1 d . . .
C2 C 0.7502(3) -0.04338(14) 0.38522(12) 0.0368(3) Uani 1 1 d . . .
H2 H 0.7275 -0.0866 0.4665 0.044 Uiso 1 1 calc R . .
C5 C 0.8132(3) 0.08595(13) 0.14021(12) 0.0321(3) Uani 1 1 d . . .
C4 C 0.6522(3) -0.02267(13) 0.19406(12) 0.0348(3) Uani 1 1 d . . .
H4 H 0.5668 -0.0513 0.1478 0.042 Uiso 1 1 calc R . .
C1 C 0.9068(3) 0.06002(14) 0.33562(12) 0.0357(3) Uani 1 1 d . . .
H1 H 0.9909 0.0866 0.3836 0.043 Uiso 1 1 calc R . .
C8 C 1.1299(3) 0.30127(14) 0.03644(13) 0.0383(3) Uani 1 1 d . . .
H8 H 1.2331 0.3732 0.0012 0.046 Uiso 1 1 calc R . .
C6 C 0.8451(3) 0.15365(14) 0.01662(12) 0.0395(4) Uani 1 1 d . . .
H6 H 0.7603 0.1268 -0.0310 0.047 Uiso 1 1 calc R . .
C7 C 0.9991(3) 0.25772(15) -0.03268(13) 0.0412(4) Uani 1 1 d . . .
H7 H 1.0184 0.3011 -0.1139 0.049 Uiso 1 1 calc R . .
C11 C 1.3781(3) 0.38063(14) 0.18152(13) 0.0376(3) Uani 1 1 d . . .
H11A H 1.2560 0.4603 0.1467 0.045 Uiso 1 1 calc R . .
H11B H 1.5173 0.3667 0.1192 0.045 Uiso 1 1 calc R . .
C13 C 0.3400(3) -0.23838(14) 0.30731(12) 0.0363(3) Uani 1 1 d . . .
H13A H 0.4745 -0.2692 0.2519 0.044 Uiso 1 1 calc R . .
H13B H 0.2119 -0.1676 0.2634 0.044 Uiso 1 1 calc R . .
C12 C 1.5143(3) 0.40158(14) 0.27161(13) 0.0380(3) Uani 1 1 d . . .
C14 C 0.1897(3) -0.35165(14) 0.39275(12) 0.0350(3) Uani 1 1 d . . .
O4 O 0.4721(2) -0.19088(10) 0.37416(8) 0.0409(3) Uani 1 1 d . . .
O1 O 1.2259(2) 0.26927(10) 0.23199(9) 0.0407(3) Uani 1 1 d . . .
O6 O 0.2134(2) -0.39949(11) 0.49695(9) 0.0479(3) Uani 1 1 d . . .
O5 O 0.0352(2) -0.39293(11) 0.34097(9) 0.0478(3) Uani 1 1 d . . .
H5O H -0.0433 -0.4551 0.3897 0.072 Uiso 1 1 calc R . .
O2 O 1.6587(3) 0.48999(11) 0.24301(10) 0.0550(3) Uani 1 1 d . . .
O3 O 1.4617(3) 0.31818(11) 0.37914(9) 0.0521(3) Uani 1 1 d . . .
H3O H 1.5448 0.3345 0.4230 0.078 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C8 1.370(2) . ?
C9 O1 1.3714(16) . ?
C9 C10 1.4274(18) . ?
C10 C1 1.4169(19) . ?
C10 C5 1.4201(18) . ?
C3 C4 1.3629(19) . ?
C3 O4 1.3760(15) . ?
C3 C2 1.4102(18) . ?
C2 C1 1.3618(19) . ?
C2 H2 0.9300 . ?
C5 C6 1.4171(19) . ?
C5 C4 1.4208(18) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C8 C7 1.4052(19) . ?
C8 H8 0.9300 . ?
C6 C7 1.3590(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C11 O1 1.4148(16) . ?
C11 C12 1.5026(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 O4 1.4145(15) . ?
C13 C14 1.4983(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 O2 1.2048(17) . ?
C12 O3 1.3080(18) . ?
C14 O6 1.2144(16) . ?
C14 O5 1.3067(16) . ?
O5 H5O 0.8200 . ?
O3 H3O 0.8200 . ?

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
C8 C9 O1 124.74(12) . . ?
C8 C9 C10 121.08(13) . . ?
O1 C9 C10 114.17(12) . . ?
C1 C10 C5 118.66(12) . . ?
C1 C10 C9 123.14(12) . . ?
C5 C10 C9 118.20(12) . . ?
C4 C3 O4 124.82(12) . . ?
C4 C3 C2 120.97(12) . . ?
O4 C3 C2 114.21(12) . . ?
C1 C2 C3 119.99(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C6 C5 C10 119.41(12) . . ?
C6 C5 C4 121.42(12) . . ?
C10 C5 C4 119.17(12) . . ?
C3 C4 C5 120.14(12) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C2 C1 C10 121.07(13) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C9 C8 C7 119.58(13) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C7 C6 C5 120.27(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.45(13) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
O1 C11 C12 111.67(11) . . ?
O1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O4 C13 C14 106.98(11) . . ?
O4 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O4 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
O2 C12 O3 124.71(14) . . ?
O2 C12 C11 120.46(13) . . ?
O3 C12 C11 114.83(12) . . ?
O6 C14 O5 124.73(13) . . ?
O6 C14 C13 123.52(12) . . ?
O5 C14 C13 111.74(11) . . ?
C3 O4 C13 117.19(10) . . ?
C9 O1 C11 116.42(11) . . ?
C14 O5 H5O 109.5 . . ?
C12 O3 H3O 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
C8 C9 C10 C1 -178.72(13) . . . . ?
O1 C9 C10 C1 1.5(2) . . . . ?
C8 C9 C10 C5 0.7(2) . . . . ?
O1 C9 C10 C5 -179.08(11) . . . . ?
C4 C3 C2 C1 -0.3(2) . . . . ?
O4 C3 C2 C1 179.54(12) . . . . ?
C1 C10 C5 C6 179.22(13) . . . . ?
C9 C10 C5 C6 -0.3(2) . . . . ?
C1 C10 C5 C4 -0.5(2) . . . . ?
C9 C10 C5 C4 -179.95(12) . . . . ?
O4 C3 C4 C5 -179.87(12) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C6 C5 C4 C3 -179.24(13) . . . . ?
C10 C5 C4 C3 0.5(2) . . . . ?
C3 C2 C1 C10 0.2(2) . . . . ?
C5 C10 C1 C2 0.1(2) . . . . ?
C9 C10 C1 C2 179.58(13) . . . . ?
O1 C9 C8 C7 178.90(13) . . . . ?
C10 C9 C8 C7 -0.9(2) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C4 C5 C6 C7 179.66(14) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C9 C8 C7 C6 0.6(2) . . . . ?
O1 C11 C12 O2 177.92(14) . . . . ?
O1 C11 C12 O3 -2.28(19) . . . . ?
O4 C13 C14 O6 -8.1(2) . . . . ?
O4 C13 C14 O5 172.81(12) . . . . ?
C4 C3 O4 C13 0.3(2) . . . . ?
C2 C3 O4 C13 -179.54(12) . . . . ?
C14 C13 O4 C3 -179.53(11) . . . . ?
C8 C9 O1 C11 2.8(2) . . . . ?
C10 C9 O1 C11 -177.45(11) . . . . ?
C12 C11 O1 C9 -176.82(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.061
# Attachment '27diester_1.cif'

data_27diester_1
_database_code_depnum_ccdc_archive 'CCDC 684225'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O6'
_chemical_formula_weight         304.29

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_H-M   P2(1)/c

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

_cell_length_a                   27.3847(10)
_cell_length_b                   6.7513(3)
_cell_length_c                   8.0896(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.669(3)
_cell_angle_gamma                90.00
_cell_volume                     1495.52(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      21.45

_exptl_crystal_description       Blocks
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            16525
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3623
_reflns_number_gt                1531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0653P)²+0.0650P] where P=(Fo²+2Fc²)/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         3623
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1758
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13773(6) 0.3502(3) 0.0053(2) 0.0564(5) Uani 1 1 d . . .
O4 O 0.36509(6) 0.3413(3) 0.4951(2) 0.0638(6) Uani 1 1 d . . .
O6 O 0.42164(8) -0.1174(4) 0.5647(3) 0.0897(8) Uani 1 1 d . . .
O5 O 0.44100(9) 0.1847(4) 0.6567(3) 0.1009(9) Uani 1 1 d . . .
O2 O 0.06278(8) 0.2011(3) -0.1697(3) 0.0829(7) Uani 1 1 d . . .
O3 O 0.07574(7) -0.1003(3) -0.0612(2) 0.0677(6) Uani 1 1 d . . .
C2 C 0.17394(9) 0.4294(4) 0.1044(3) 0.0452(7) Uani 1 1 d . . .
C3 C 0.16648(10) 0.6290(4) 0.1463(3) 0.0508(7) Uani 1 1 d . . .
H3 H 0.1391 0.6959 0.1061 0.061 Uiso 1 1 calc R . .
C4 C 0.19932(10) 0.7242(4) 0.2459(3) 0.0512(7) Uani 1 1 d . . .
H4 H 0.1941 0.8561 0.2737 0.061 Uiso 1 1 calc R . .
C5 C 0.24127(9) 0.6252(4) 0.3076(3) 0.0463(7) Uani 1 1 d . . .
C6 C 0.27578(10) 0.7177(4) 0.4140(3) 0.0560(8) Uani 1 1 d . . .
H6 H 0.2710 0.8488 0.4450 0.067 Uiso 1 1 calc R . .
C7 C 0.31573(11) 0.6197(4) 0.4720(4) 0.0598(8) Uani 1 1 d . . .
H7 H 0.3379 0.6835 0.5419 0.072 Uiso 1 1 calc R . .
C8 C 0.32348(9) 0.4225(4) 0.4262(3) 0.0504(7) Uani 1 1 d . . .
C9 C 0.29128(9) 0.3244(4) 0.3244(3) 0.0460(7) Uani 1 1 d . . .
H9 H 0.2971 0.1934 0.2951 0.055 Uiso 1 1 calc R . .
C10 C 0.24902(9) 0.4240(3) 0.2638(3) 0.0428(6) Uani 1 1 d . . .
C1 C 0.21409(9) 0.3285(4) 0.1612(3) 0.0467(7) Uani 1 1 d . . .
H1 H 0.2184 0.1964 0.1322 0.056 Uiso 1 1 calc R . .
C14 C 0.37339(10) 0.1370(4) 0.4705(4) 0.0595(8) Uani 1 1 d . . .
H14A H 0.3802 0.1112 0.3551 0.071 Uiso 1 1 calc R . .
H14B H 0.3447 0.0616 0.5010 0.071 Uiso 1 1 calc R . .
C15 C 0.41620(11) 0.0778(5) 0.5764(4) 0.0637(8) Uani 1 1 d . . .
C16 C 0.46017(14) -0.2091(7) 0.6614(6) 0.1224(16) Uani 1 1 d . . .
H16A H 0.4911 -0.1567 0.6283 0.184 Uiso 1 1 calc R . .
H16B H 0.4597 -0.3497 0.6435 0.184 Uiso 1 1 calc R . .
H16C H 0.4553 -0.1819 0.7765 0.184 Uiso 1 1 calc R . .
C12 C 0.08553(10) 0.0909(5) -0.0827(3) 0.0532(7) Uani 1 1 d . . .
C13 C 0.03617(12) -0.1854(6) -0.1571(5) 0.0933(12) Uani 1 1 d . . .
H13A H 0.0056 -0.1342 -0.1185 0.140 Uiso 1 1 calc R . .
H13B H 0.0366 -0.3268 -0.1449 0.140 Uiso 1 1 calc R . .
H13C H 0.0400 -0.1517 -0.2715 0.140 Uiso 1 1 calc R . .
C11 C 0.13030(9) 0.1440(4) 0.0160(3) 0.0487(7) Uani 1 1 d . . .
H11A H 0.1262 0.1056 0.1306 0.058 Uiso 1 1 calc R . .
H11B H 0.1584 0.0743 -0.0269 0.058 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.376(3) . ?
O1 C11 1.410(3) . ?
O4 C8 1.376(3) . ?
O4 C14 1.413(3) . ?
O6 C15 1.330(4) . ?
O6 C16 1.445(4) . ?
O5 C15 1.181(3) . ?
O2 C12 1.194(3) . ?
O3 C12 1.330(3) . ?
O3 C13 1.445(3) . ?
C2 C1 1.368(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(3) . ?
C5 C10 1.420(3) . ?
C6 C7 1.357(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.399(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(3) . ?
C9 C10 1.421(3) . ?
C9 H9 0.9300 . ?
C10 C1 1.415(3) . ?
C1 H1 0.9300 . ?
C14 C15 1.499(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 C11 1.499(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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 O1 C11 116.84(19) . . ?
C8 O4 C14 117.7(2) . . ?
C15 O6 C16 117.9(3) . . ?
C12 O3 C13 117.8(3) . . ?
C1 C2 O1 124.9(2) . . ?
C1 C2 C3 121.0(2) . . ?
O1 C2 C3 114.1(2) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 122.7(2) . . ?
C6 C5 C10 118.2(2) . . ?
C4 C5 C10 119.1(2) . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 O4 125.1(3) . . ?
C9 C8 C7 121.4(3) . . ?
O4 C8 C7 113.5(2) . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C1 C10 C5 118.7(2) . . ?
C1 C10 C9 122.0(2) . . ?
C5 C10 C9 119.3(2) . . ?
C2 C1 C10 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C10 C1 H1 119.8 . . ?
O4 C14 C15 107.8(2) . . ?
O4 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
O5 C15 O6 125.5(3) . . ?
O5 C15 C14 126.4(3) . . ?
O6 C15 C14 108.1(3) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C12 O3 125.2(3) . . ?
O2 C12 C11 125.7(3) . . ?
O3 C12 C11 109.1(2) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C11 C12 108.7(2) . . ?
O1 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O1 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.045

