# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1488933'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

#===============================================================================

# 4. CHEMICAL DATA

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            1-Dimer
_chemical_melting_point          403
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 O6'
_chemical_formula_weight         256.25

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'

#===============================================================================

# 5. CRYSTAL DATA

_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                   4.1534(8)
_cell_length_b                   7.3467(10)
_cell_length_c                   10.0543(14)
_cell_angle_alpha                103.074(13)
_cell_angle_beta                 94.848(14)
_cell_angle_gamma                98.213(16)
_cell_volume                     293.60(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    110
_cell_measurement_reflns_used    628
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      67.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             136
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8416
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110
_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  'Bruker Apex2 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1907
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         70.24
_reflns_number_total             963
_reflns_number_gt                743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

_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)+(0.1106P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         963
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.2272(4) 0.3019(2) 0.63307(17) 0.0269(5) Uani 1 1 d . . .
H1 H 0.149(10) 0.381(6) 0.577(5) 0.083(14) Uiso 1 1 d . . .
O2 O 0.1391(4) 0.3925(2) 0.39603(18) 0.0308(5) Uani 1 1 d . . .
O3 O 0.3066(4) 0.2093(2) 0.21272(17) 0.0265(5) Uani 1 1 d . . .
C1 C 0.3590(6) 0.1591(3) 0.5609(3) 0.0245(6) Uani 1 1 d . . .
C2 C 0.3826(6) 0.1262(3) 0.4244(3) 0.0250(6) Uani 1 1 d . . .
C3 C 0.5188(6) -0.0418(3) 0.3493(3) 0.0247(6) Uani 1 1 d . . .
H3A H 0.349(7) -0.128(4) 0.279(3) 0.032(7) Uiso 1 1 d . . .
H3B H 0.694(6) -0.009(4) 0.302(3) 0.019(6) Uiso 1 1 d . . .
C4 C 0.2662(6) 0.2556(3) 0.3468(2) 0.0237(6) Uani 1 1 d . . .
C5 C 0.1944(7) 0.3360(4) 0.1331(3) 0.0291(7) Uani 1 1 d . . .
H5A H 0.336(7) 0.463(4) 0.172(3) 0.039(8) Uiso 1 1 d . . .
H5B H -0.039(7) 0.342(4) 0.146(3) 0.026(7) Uiso 1 1 d . . .
C6 C 0.2364(7) 0.2548(4) -0.0147(3) 0.0322(7) Uani 1 1 d . . .
H6A H 0.464(8) 0.241(4) -0.024(3) 0.042(8) Uiso 1 1 d . . .
H6B H 0.169(6) 0.340(4) -0.066(3) 0.022(6) Uiso 1 1 d . . .
H6C H 0.096(8) 0.128(5) -0.052(4) 0.047(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.347(3) . ?
O1 H1 0.97(4) . ?
O2 C4 1.228(3) . ?
O3 C4 1.344(3) . ?
O3 C5 1.457(3) . ?
C1 C2 1.353(4) . ?
C1 C3 1.488(3) 2_656 ?
C2 C4 1.466(3) . ?
C2 C3 1.505(3) . ?
C3 C1 1.488(3) 2_656 ?
C3 H3A 0.99(3) . ?
C3 H3B 0.93(3) . ?
C5 C6 1.505(4) . ?
C5 H5A 1.01(3) . ?
C5 H5B 1.00(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.96(3) . ?
C6 H6C 1.00(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113(3) . . ?
C4 O3 C5 114.76(18) . . ?
O1 C1 C2 124.8(2) . . ?
O1 C1 C3 111.4(2) . 2_656 ?
C2 C1 C3 123.8(2) . 2_656 ?
C1 C2 C4 119.2(2) . . ?
C1 C2 C3 121.8(2) . . ?
C4 C2 C3 118.9(2) . . ?
C1 C3 C2 114.3(2) 2_656 . ?
C1 C3 H3A 106.1(16) 2_656 . ?
C2 C3 H3A 110.8(15) . . ?
C1 C3 H3B 105.4(15) 2_656 . ?
C2 C3 H3B 113.5(15) . . ?
H3A C3 H3B 106(2) . . ?
O2 C4 O3 121.8(2) . . ?
O2 C4 C2 124.6(2) . . ?
O3 C4 C2 113.6(2) . . ?
O3 C5 C6 107.19(19) . . ?
O3 C5 H5A 106.3(16) . . ?
C6 C5 H5A 112.1(18) . . ?
O3 C5 H5B 107.5(15) . . ?
C6 C5 H5B 112.2(15) . . ?
H5A C5 H5B 111(2) . . ?
C5 C6 H6A 110.7(19) . . ?
C5 C6 H6B 107.0(17) . . ?
H6A C6 H6B 111(3) . . ?
C5 C6 H6C 112(2) . . ?
H6A C6 H6C 108(3) . . ?
H6B C6 H6C 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C4 1.7(4) . . . . ?
C3 C1 C2 C4 -177.5(2) 2_656 . . . ?
O1 C1 C2 C3 -177.1(2) . . . . ?
C3 C1 C2 C3 3.8(4) 2_656 . . . ?
C1 C2 C3 C1 -3.4(4) . . . 2_656 ?
C4 C2 C3 C1 177.8(2) . . . 2_656 ?
C5 O3 C4 O2 1.2(3) . . . . ?
C5 O3 C4 C2 -179.8(2) . . . . ?
C1 C2 C4 O2 -1.7(4) . . . . ?
C3 C2 C4 O2 177.1(2) . . . . ?
C1 C2 C4 O3 179.2(2) . . . . ?
C3 C2 C4 O3 -2.0(3) . . . . ?
C4 O3 C5 C6 -176.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        70.24
_diffrn_measured_fraction_theta_full 0.862
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1488934'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

#===============================================================================

# 4. CHEMICAL DATA

_chemical_name_systematic        
;               
'2,2-Methylenebis(2-acetoxymethyl-1,3-dithianyl)'
;
_chemical_name_common            8-(OAc)2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H24 O4 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         396.58
_chemical_melting_point          375

#===============================================================================

# 5. CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0126(2)
_cell_length_b                   13.6758(3)
_cell_length_c                   13.4101(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.1860(10)
_cell_angle_gamma                90
_cell_volume                     1828.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    427
_cell_measurement_theta_min      3.6091
_cell_measurement_theta_max      33.1380
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.192
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            46949
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         35.16
_diffrn_reflns_theta_full        35.16
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             8114
_reflns_number_gt                7048
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0673
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         8114
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.3690P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.263
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2015.5-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.48703(2) 0.21556(2) 0.15557(2) 0.01155(4) Uani d . . . 1 . .
S S2 0.29347(2) 0.07361(2) 0.04415(2) 0.01109(4) Uani d . . . 1 . .
S S3 0.32110(2) 0.00988(2) 0.41924(2) 0.01199(4) Uani d . . . 1 . .
S S4 0.25081(2) -0.08163(2) 0.21765(2) 0.01171(4) Uani d . . . 1 . .
O O1 0.08284(6) 0.21236(4) 0.12637(4) 0.01342(10) Uani d . . . 1 . .
O O3 0.56811(6) 0.06858(4) 0.32671(4) 0.01130(10) Uani d . . . 1 . .
O O4 0.74816(7) 0.00251(5) 0.26442(6) 0.02506(15) Uani d . . . 1 . .
O O2 0.03977(7) 0.23628(5) -0.04036(5) 0.02053(13) Uani d . . . 1 . .
C C9 -0.11820(10) 0.14861(7) 0.05131(8) 0.02471(19) Uani d . . . 1 . .
H H9A -0.1787 0.1527 -0.0102 0.037 Uiso calc U . R 1 . .
H H9B -0.1617 0.1775 0.1069 0.037 Uiso calc U . R 1 . .
H H9C -0.097 0.0799 0.0663 0.037 Uiso calc U . R 1 . .
C C8 0.00822(8) 0.20314(6) 0.03745(7) 0.01538(14) Uani d . . . 1 . .
C C7 0.21774(8) 0.24928(5) 0.12629(6) 0.01205(13) Uani d . . . 1 . .
H H7A 0.2347 0.299 0.1796 0.014 Uiso calc U . R 1 . .
H H7B 0.2296 0.2806 0.0611 0.014 Uiso calc U . R 1 . .
C C1 0.31755(7) 0.16396(5) 0.14447(5) 0.00938(11) Uani d . . . 1 . .
C C2 0.29360(7) 0.12141(5) 0.24877(5) 0.00977(11) Uani d . . . 1 . .
H H2A 0.3342 0.1682 0.299 0.012 Uiso calc U . R 1 . .
H H2B 0.1956 0.1236 0.2537 0.012 Uiso calc U . R 1 . .
C C3 0.34047(7) 0.01891(5) 0.28432(6) 0.00928(11) Uani d . . . 1 . .
C C13 0.48689(7) -0.00386(5) 0.27130(6) 0.01105(12) Uani d . . . 1 . .
H H13A 0.5101 -0.0701 0.2971 0.013 Uiso calc U . R 1 . .
H H13B 0.5027 -0.0014 0.1995 0.013 Uiso calc U . R 1 . .
C C14 0.69897(8) 0.06606(6) 0.31169(6) 0.01322(13) Uani d . . . 1 . .
C C15 0.77248(8) 0.15134(6) 0.35972(7) 0.01708(15) Uani d . . . 1 . .
H H15A 0.868 0.1461 0.3499 0.026 Uiso calc U . R 1 . .
H H15B 0.7612 0.1519 0.4315 0.026 Uiso calc U . R 1 . .
H H15C 0.7365 0.2121 0.3292 0.026 Uiso calc U . R 1 . .
C C4 0.50701(9) 0.25901(6) 0.02991(6) 0.01541(14) Uani d . . . 1 . .
H H4A 0.4426 0.3129 0.0138 0.018 Uiso calc U . R 1 . .
H H4B 0.5985 0.286 0.0284 0.018 Uiso calc U . R 1 . .
C C5 0.48527(9) 0.18065(6) -0.05039(6) 0.01631(14) Uani d . . . 1 . .
H H5A 0.5461 0.125 -0.0329 0.02 Uiso calc U . R 1 . .
H H5B 0.5084 0.2076 -0.1151 0.02 Uiso calc U . R 1 . .
C C6 0.34112(8) 0.14405(6) -0.06191(6) 0.01494(14) Uani d . . . 1 . .
H H6A 0.3283 0.1029 -0.1228 0.018 Uiso calc U . R 1 . .
H H6B 0.2803 0.201 -0.0719 0.018 Uiso calc U . R 1 . .
C C10 0.14006(8) 0.01381(6) 0.41997(6) 0.01555(14) Uani d . . . 1 . .
H H10A 0.1172 0.0107 0.4902 0.019 Uiso calc U . R 1 . .
H H10B 0.1073 0.0773 0.3919 0.019 Uiso calc U . R 1 . .
C C11 0.06684(9) -0.06830(7) 0.36088(7) 0.01805(15) Uani d . . . 1 . .
H H11A 0.1023 -0.1318 0.3868 0.022 Uiso calc U . R 1 . .
H H11B -0.0295 -0.0655 0.372 0.022 Uiso calc U . R 1 . .
C C12 0.08070(8) -0.06342(6) 0.24920(7) 0.01606(14) Uani d . . . 1 . .
H H12A 0.0488 0.0012 0.2237 0.019 Uiso calc U . R 1 . .
H H12B 0.0224 -0.1139 0.215 0.019 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 . 1.8150(8) ?
S1 C1 . 1.8313(7) ?
S2 C6 . 1.8169(8) ?
S2 C1 . 1.8266(7) ?
S3 C10 . 1.8144(8) ?
S3 C3 . 1.8411(8) ?
S4 C12 . 1.8090(9) ?
S4 C3 . 1.8305(7) ?
O1 C8 . 1.3545(10) ?
O1 C7 . 1.4421(10) ?
O3 C14 . 1.3440(9) ?
O3 C13 . 1.4443(9) ?
O4 C14 . 1.2067(10) ?
O2 C8 . 1.2056(11) ?
C9 C8 . 1.4951(13) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C7 C1 . 1.5412(10) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C1 C2 . 1.5534(10) ?
C2 C3 . 1.5402(10) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C13 . 1.5242(10) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.4937(11) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C4 C5 . 1.5208(12) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.5223(12) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C10 C11 . 1.5236(12) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.5179(13) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 S1 C1 . . 103.28(4) ?
C6 S2 C1 . . 101.03(4) ?
C10 S3 C3 . . 101.38(4) ?
C12 S4 C3 . . 102.29(4) ?
C8 O1 C7 . . 118.29(7) ?
C14 O3 C13 . . 114.61(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 ?
O2 C8 O1 . . 124.07(8) ?
O2 C8 C9 . . 125.88(8) ?
O1 C8 C9 . . 110.05(8) ?
O1 C7 C1 . . 109.20(6) ?
O1 C7 H7A . . 109.8 ?
C1 C7 H7A . . 109.8 ?
O1 C7 H7B . . 109.8 ?
C1 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.3 ?
C7 C1 C2 . . 105.98(6) ?
C7 C1 S2 . . 110.80(5) ?
C2 C1 S2 . . 112.89(5) ?
C7 C1 S1 . . 107.70(5) ?
C2 C1 S1 . . 106.76(5) ?
S2 C1 S1 . . 112.35(4) ?
C3 C2 C1 . . 123.51(6) ?
C3 C2 H2A . . 106.5 ?
C1 C2 H2A . . 106.5 ?
C3 C2 H2B . . 106.5 ?
C1 C2 H2B . . 106.5 ?
H2A C2 H2B . . 106.5 ?
C13 C3 C2 . . 114.82(6) ?
C13 C3 S4 . . 103.00(5) ?
C2 C3 S4 . . 114.22(5) ?
C13 C3 S3 . . 106.66(5) ?
C2 C3 S3 . . 108.00(5) ?
S4 C3 S3 . . 109.82(4) ?
O3 C13 C3 . . 107.67(6) ?
O3 C13 H13A . . 110.2 ?
C3 C13 H13A . . 110.2 ?
O3 C13 H13B . . 110.2 ?
C3 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
O4 C14 O3 . . 123.16(7) ?
O4 C14 C15 . . 125.46(8) ?
O3 C14 C15 . . 111.37(7) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C5 C4 S1 . . 113.95(6) ?
C5 C4 H4A . . 108.8 ?
S1 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
S1 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C6 . . 112.16(7) ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5B . . 109.2 ?
C6 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C5 C6 S2 . . 114.11(6) ?
C5 C6 H6A . . 108.7 ?
S2 C6 H6A . . 108.7 ?
C5 C6 H6B . . 108.7 ?
S2 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
C11 C10 S3 . . 114.16(6) ?
C11 C10 H10A . . 108.7 ?
S3 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
S3 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C12 C11 C10 . . 113.47(7) ?
C12 C11 H11A . . 108.9 ?
C10 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C10 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C11 C12 S4 . . 113.37(6) ?
C11 C12 H12A . . 108.9 ?
S4 C12 H12A . . 108.9 ?
C11 C12 H12B . . 108.9 ?
S4 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 C8 O2 . . . . -10.83(12) ?
C7 O1 C8 C9 . . . . 170.49(7) ?
C8 O1 C7 C1 . . . . -104.71(7) ?
O1 C7 C1 C2 . . . . -60.78(7) ?
O1 C7 C1 S2 . . . . 62.01(7) ?
O1 C7 C1 S1 . . . . -174.75(5) ?
C6 S2 C1 C7 . . . . 65.48(6) ?
C6 S2 C1 C2 . . . . -175.83(5) ?
C6 S2 C1 S1 . . . . -55.03(5) ?
C4 S1 C1 C7 . . . . -68.47(6) ?
C4 S1 C1 C2 . . . . 178.08(5) ?
C4 S1 C1 S2 . . . . 53.81(5) ?
C7 C1 C2 C3 . . . . 161.70(6) ?
S2 C1 C2 C3 . . . . 40.25(8) ?
S1 C1 C2 C3 . . . . -83.68(7) ?
C1 C2 C3 C13 . . . . 49.97(9) ?
C1 C2 C3 S4 . . . . -68.70(8) ?
C1 C2 C3 S3 . . . . 168.81(5) ?
C12 S4 C3 C13 . . . . 172.01(5) ?
C12 S4 C3 C2 . . . . -62.81(6) ?
C12 S4 C3 S3 . . . . 58.68(5) ?
C10 S3 C3 C13 . . . . -168.99(5) ?
C10 S3 C3 C2 . . . . 67.10(5) ?
C10 S3 C3 S4 . . . . -58.05(5) ?
C14 O3 C13 C3 . . . . -171.56(6) ?
C2 C3 C13 O3 . . . . 58.57(8) ?
S4 C3 C13 O3 . . . . -176.64(5) ?
S3 C3 C13 O3 . . . . -61.02(6) ?
C13 O3 C14 O4 . . . . -7.50(12) ?
C13 O3 C14 C15 . . . . 171.97(7) ?
C1 S1 C4 C5 . . . . -56.21(7) ?
S1 C4 C5 C6 . . . . 65.60(8) ?
C4 C5 C6 S2 . . . . -68.94(8) ?
C1 S2 C6 C5 . . . . 60.87(7) ?
C3 S3 C10 C11 . . . . 59.50(7) ?
S3 C10 C11 C12 . . . . -65.47(9) ?
C10 C11 C12 S4 . . . . 65.16(9) ?
C3 S4 C12 C11 . . . . -59.97(7) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1488935'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

#===============================================================================

# 4. CHEMICAL DATA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
15-Oxa-1,5,9,13-tetrathiadispiro[5.1.58.36]hexadecan-14-ol 
;
_chemical_name_common            8-OH/O
_chemical_melting_point          431
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 O2 S4'
_chemical_formula_weight         310.49

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'

#===============================================================================

# 5. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   18.0071(8)
_cell_length_b                   6.3969(3)
_cell_length_c                   23.9129(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.280(2)
_cell_angle_gamma                90.00
_cell_volume                     2753.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9728
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      40.53
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_T_max  0.8468
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110
_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-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            111083
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         43.21
_reflns_number_total             9496
_reflns_number_gt                7875
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    XS
_computing_structure_refinement  XL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

_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)+(0.0340P)²+1.5866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9496
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.003
_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 0.30977(3) 0.48599(11) 0.78886(2) 0.01564(11) Uani 1 1 d . . .
O2 O 0.19484(4) 0.56075(11) 0.75377(3) 0.01806(12) Uani 1 1 d . . .
H2 H 0.2059(11) 0.649(3) 0.7313(8) 0.053(5) Uiso 1 1 d . . .
C1 C 0.24204(4) 0.59698(13) 0.79910(3) 0.01378(12) Uani 1 1 d . . .
H1 H 0.2543(7) 0.741(2) 0.8045(5) 0.013(3) Uiso 1 1 d . . .
C2 C 0.20864(4) 0.51676(12) 0.85360(3) 0.01141(11) Uani 1 1 d . . .
C3 C 0.26825(4) 0.54247(12) 0.90083(3) 0.01219(11) Uani 1 1 d . . .
H3A H 0.2720(8) 0.686(2) 0.9058(6) 0.022(3) Uiso 1 1 d . . .
H3B H 0.2513(7) 0.478(2) 0.9353(5) 0.014(3) Uiso 1 1 d . . .
C4 C 0.34667(4) 0.46353(13) 0.88704(3) 0.01292(12) Uani 1 1 d . . .
C5 C 0.36602(5) 0.54150(15) 0.82862(4) 0.01666(14) Uani 1 1 d . . .
H5A H 0.3722(7) 0.693(2) 0.8299(6) 0.018(3) Uiso 1 1 d . . .
H5B H 0.4136(8) 0.480(2) 0.8158(6) 0.022(3) Uiso 1 1 d . . .
S1 S 0.134675(11) 0.69044(3) 0.876468(9) 0.01513(4) Uani 1 1 d . . .
C6 C 0.05667(5) 0.62671(15) 0.83052(4) 0.01844(14) Uani 1 1 d . . .
H6A H 0.0179(9) 0.714(2) 0.8442(6) 0.028(4) Uiso 1 1 d . . .
H6B H 0.0672(8) 0.671(2) 0.7934(6) 0.025(4) Uiso 1 1 d . . .
C7 C 0.03411(5) 0.39802(15) 0.83275(4) 0.01857(15) Uani 1 1 d . . .
H7A H -0.0129(8) 0.382(2) 0.8103(6) 0.022(3) Uiso 1 1 d . . .
H7B H 0.0219(8) 0.359(2) 0.8712(6) 0.021(3) Uiso 1 1 d . . .
C8 C 0.09282(5) 0.25100(14) 0.81030(4) 0.01738(14) Uani 1 1 d . . .
H8A H 0.1034(8) 0.284(2) 0.7717(5) 0.019(3) Uiso 1 1 d . . .
H8B H 0.0762(7) 0.105(2) 0.8123(5) 0.018(3) Uiso 1 1 d . . .
S2 S 0.180141(11) 0.24321(3) 0.849993(8) 0.01264(4) Uani 1 1 d . . .
S3 S 0.416678(11) 0.58200(3) 0.933655(9) 0.01647(4) Uani 1 1 d . . .
S4 S 0.356769(11) 0.17946(3) 0.886638(8) 0.01473(4) Uani 1 1 d . . .
C9 C 0.39591(5) 0.45852(16) 0.99989(4) 0.01906(15) Uani 1 1 d . . .
H9A H 0.4303(8) 0.516(2) 1.0234(6) 0.026(4) Uiso 1 1 d . . .
H9B H 0.3464(8) 0.503(2) 1.0119(6) 0.023(3) Uiso 1 1 d . . .
C10 C 0.40226(6) 0.22200(16) 0.99883(4) 0.02062(16) Uani 1 1 d . . .
H10A H 0.3934(9) 0.170(2) 1.0356(7) 0.031(4) Uiso 1 1 d . . .
H10B H 0.4531(8) 0.181(2) 0.9883(6) 0.024(4) Uiso 1 1 d . . .
C11 C 0.34508(5) 0.11957(14) 0.95986(4) 0.01814(14) Uani 1 1 d . . .
H11A H 0.2957(8) 0.160(2) 0.9704(6) 0.020(3) Uiso 1 1 d . . .
H11B H 0.3489(8) -0.023(2) 0.9620(6) 0.023(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.4188(10) . ?
O1 C1 1.4370(10) . ?
O2 C1 1.3820(10) . ?
O2 H2 0.81(2) . ?
C1 C2 1.5357(11) . ?
C1 H1 0.957(13) . ?
C2 C3 1.5493(11) . ?
C2 S2 1.8251(8) . ?
C2 S1 1.8276(8) . ?
C3 C4 1.5423(11) . ?
C3 H3A 0.928(15) . ?
C3 H3B 0.977(13) . ?
C4 C5 1.5310(11) . ?
C4 S4 1.8263(8) . ?
C4 S3 1.8284(8) . ?
C5 H5A 0.977(14) . ?
C5 H5B 0.997(14) . ?
S1 C6 1.8103(9) . ?
C6 C7 1.5195(13) . ?
C6 H6A 0.956(16) . ?
C6 H6B 0.955(15) . ?
C7 C8 1.5218(13) . ?
C7 H7A 0.998(14) . ?
C7 H7B 0.982(14) . ?
C8 S2 1.8192(9) . ?
C8 H8A 0.970(13) . ?
C8 H8B 0.980(14) . ?
S3 C9 1.8163(10) . ?
S4 C11 1.8093(9) . ?
C9 C10 1.5176(14) . ?
C9 H9A 0.905(15) . ?
C9 H9B 0.985(14) . ?
C10 C11 1.5215(14) . ?
C10 H10A 0.957(16) . ?
C10 H10B 0.990(15) . ?
C11 H11A 0.963(14) . ?
C11 H11B 0.917(15) . ?

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 O1 C1 110.98(6) . . ?
C1 O2 H2 104.4(13) . . ?
O2 C1 O1 107.03(7) . . ?
O2 C1 C2 111.34(6) . . ?
O1 C1 C2 109.24(6) . . ?
O2 C1 H1 113.8(8) . . ?
O1 C1 H1 107.7(8) . . ?
C2 C1 H1 107.6(8) . . ?
C1 C2 C3 107.76(6) . . ?
C1 C2 S2 113.28(5) . . ?
C3 C2 S2 109.01(5) . . ?
C1 C2 S1 110.65(5) . . ?
C3 C2 S1 102.42(5) . . ?
S2 C2 S1 113.01(4) . . ?
C4 C3 C2 115.61(6) . . ?
C4 C3 H3A 106.7(9) . . ?
C2 C3 H3A 104.3(9) . . ?
C4 C3 H3B 110.3(7) . . ?
C2 C3 H3B 110.1(7) . . ?
H3A C3 H3B 109.6(11) . . ?
C5 C4 C3 108.45(6) . . ?
C5 C4 S4 107.13(6) . . ?
C3 C4 S4 114.75(5) . . ?
C5 C4 S3 104.68(5) . . ?
C3 C4 S3 110.86(5) . . ?
S4 C4 S3 110.38(4) . . ?
O1 C5 C4 110.88(7) . . ?
O1 C5 H5A 110.4(8) . . ?
C4 C5 H5A 108.9(8) . . ?
O1 C5 H5B 107.4(8) . . ?
C4 C5 H5B 111.5(8) . . ?
H5A C5 H5B 107.7(12) . . ?
C6 S1 C2 104.02(4) . . ?
C7 C6 S1 113.58(6) . . ?
C7 C6 H6A 110.5(9) . . ?
S1 C6 H6A 102.9(9) . . ?
C7 C6 H6B 112.3(9) . . ?
S1 C6 H6B 109.2(9) . . ?
H6A C6 H6B 107.8(13) . . ?
C6 C7 C8 113.22(7) . . ?
C6 C7 H7A 107.7(8) . . ?
C8 C7 H7A 109.5(8) . . ?
C6 C7 H7B 110.1(8) . . ?
C8 C7 H7B 110.1(8) . . ?
H7A C7 H7B 105.9(11) . . ?
C7 C8 S2 115.60(6) . . ?
C7 C8 H8A 110.7(8) . . ?
S2 C8 H8A 108.4(8) . . ?
C7 C8 H8B 110.8(8) . . ?
S2 C8 H8B 102.1(8) . . ?
H8A C8 H8B 108.8(11) . . ?
C8 S2 C2 103.73(4) . . ?
C9 S3 C4 101.46(4) . . ?
C11 S4 C4 101.06(4) . . ?
C10 C9 S3 113.70(6) . . ?
C10 C9 H9A 111.3(10) . . ?
S3 C9 H9A 102.4(9) . . ?
C10 C9 H9B 111.0(9) . . ?
S3 C9 H9B 109.6(8) . . ?
H9A C9 H9B 108.4(12) . . ?
C9 C10 C11 112.92(8) . . ?
C9 C10 H10A 108.6(10) . . ?
C11 C10 H10A 106.7(10) . . ?
C9 C10 H10B 109.7(9) . . ?
C11 C10 H10B 110.4(8) . . ?
H10A C10 H10B 108.4(13) . . ?
C10 C11 S4 114.20(7) . . ?
C10 C11 H11A 109.9(8) . . ?
S4 C11 H11A 108.9(8) . . ?
C10 C11 H11B 110.2(9) . . ?
S4 C11 H11B 104.7(9) . . ?
H11A C11 H11B 108.7(12) . . ?

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
C5 O1 C1 O2 170.32(6) . . . . ?
C5 O1 C1 C2 -69.01(8) . . . . ?
O2 C1 C2 C3 174.16(6) . . . . ?
O1 C1 C2 C3 56.17(8) . . . . ?
O2 C1 C2 S2 53.48(8) . . . . ?
O1 C1 C2 S2 -64.51(7) . . . . ?
O2 C1 C2 S1 -74.61(7) . . . . ?
O1 C1 C2 S1 167.39(5) . . . . ?
C1 C2 C3 C4 -47.37(9) . . . . ?
S2 C2 C3 C4 75.95(7) . . . . ?
S1 C2 C3 C4 -164.10(6) . . . . ?
C2 C3 C4 C5 45.52(9) . . . . ?
C2 C3 C4 S4 -74.20(8) . . . . ?
C2 C3 C4 S3 159.92(5) . . . . ?
C1 O1 C5 C4 67.52(9) . . . . ?
C3 C4 C5 O1 -53.20(9) . . . . ?
S4 C4 C5 O1 71.19(8) . . . . ?
S3 C4 C5 O1 -171.59(6) . . . . ?
C1 C2 S1 C6 76.50(6) . . . . ?
C3 C2 S1 C6 -168.87(5) . . . . ?
S2 C2 S1 C6 -51.74(5) . . . . ?
C2 S1 C6 C7 57.75(7) . . . . ?
S1 C6 C7 C8 -66.19(9) . . . . ?
C6 C7 C8 S2 64.69(9) . . . . ?
C7 C8 S2 C2 -54.00(7) . . . . ?
C1 C2 S2 C8 -77.35(6) . . . . ?
C3 C2 S2 C8 162.68(5) . . . . ?
S1 C2 S2 C8 49.51(5) . . . . ?
C5 C4 S3 C9 -173.85(6) . . . . ?
C3 C4 S3 C9 69.40(6) . . . . ?
S4 C4 S3 C9 -58.88(5) . . . . ?
C5 C4 S4 C11 172.29(5) . . . . ?
C3 C4 S4 C11 -67.25(6) . . . . ?
S3 C4 S4 C11 58.88(5) . . . . ?
C4 S3 C9 C10 59.75(7) . . . . ?
S3 C9 C10 C11 -65.21(10) . . . . ?
C9 C10 C11 S4 65.82(9) . . . . ?
C4 S4 C11 C10 -60.25(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.81(2) 2.23(2) 2.9055(10) 142.1(18) 4_556
O2 H2 S2 0.81(2) 2.92(2) 3.5829(7) 140.8(17) 4_556

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        39.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.080


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_global
_database_code_depnum_ccdc_archive 'CCDC 1488936'
_audit_update_record             
;
2016-06-29 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

#===============================================================================

# 4. CHEMICAL DATA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
altaicadispirolactone 
;
_chemical_name_common            altaicadispirolactone
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 O6'
_chemical_formula_weight         228.20

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'

#===============================================================================

# 5. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   10.5040(4)
_cell_length_b                   7.8964(3)
_cell_length_c                   6.3078(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0813(19)
_cell_angle_gamma                90.00
_cell_volume                     505.17(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    110
_cell_measurement_reflns_used    9689
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      39.17
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110
_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-Nonius Kappa Axis X8 Apex2'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23709
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         39.55
_reflns_number_total             2899
_reflns_number_gt                2329
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Apex2
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    XS
_computing_structure_refinement  XL
_computing_molecular_graphics    NRCVAX
_computing_publication_material  cif2tables.py

_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)+(0.0701P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2899
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.15073(6) 0.17266(8) 0.76413(10) 0.02750(14) Uani 1 1 d . . .
O2 O 0.32740(5) 0.32510(6) 0.92921(8) 0.01621(10) Uani 1 1 d . . .
O3 O 0.41876(4) 0.55965(6) 0.80069(7) 0.01648(10) Uani 1 1 d . . .
C1 C 0.19857(6) 0.30983(9) 0.81697(11) 0.01971(13) Uani 1 1 d . . .
C2 C 0.13556(7) 0.48220(11) 0.77630(12) 0.02513(15) Uani 1 1 d . . .
H2A H 0.0479(12) 0.4809(15) 0.797(2) 0.027(3) Uiso 1 1 d . . .
H2B H 0.1353(11) 0.5167(18) 0.618(2) 0.034(3) Uiso 1 1 d . . .
C3 C 0.23128(7) 0.59478(9) 0.93963(12) 0.02096(13) Uani 1 1 d . . .
H3A H 0.2390(12) 0.7136(16) 0.891(2) 0.029(3) Uiso 1 1 d . . .
H3B H 0.2079(12) 0.5970(16) 1.076(2) 0.025(3) Uiso 1 1 d . . .
C4 C 0.36197(6) 0.50271(7) 0.96679(10) 0.01514(11) Uani 1 1 d . . .
C5 C 0.45717(6) 0.51918(8) 1.19181(10) 0.01614(11) Uani 1 1 d . . .
H5A H 0.4714(11) 0.6350(17) 1.227(2) 0.028(3) Uiso 1 1 d . . .
H5B H 0.4216(10) 0.4606(14) 1.3022(17) 0.016(2) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2041(9) . ?
O2 C1 1.3596(8) . ?
O2 C4 1.4527(7) . ?
O3 C4 1.4074(8) . ?
O3 C5 1.4339(8) 3_667 ?
C1 C2 1.5060(11) . ?
C2 C3 1.5243(11) . ?
C2 H2A 0.964(12) . ?
C2 H2B 1.037(12) . ?
C3 C4 1.5232(9) . ?
C3 H3A 0.997(13) . ?
C3 H3B 0.955(12) . ?
C4 C5 1.5142(8) . ?
C5 O3 1.4339(8) 3_667 ?
C5 H5A 0.944(14) . ?
C5 H5B 0.987(11) . ?

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 O2 C4 110.08(5) . . ?
C4 O3 C5 113.23(5) . 3_667 ?
O1 C1 O2 120.74(7) . . ?
O1 C1 C2 129.24(7) . . ?
O2 C1 C2 110.02(6) . . ?
C1 C2 C3 103.21(5) . . ?
C1 C2 H2A 111.1(7) . . ?
C3 C2 H2A 113.5(7) . . ?
C1 C2 H2B 107.0(8) . . ?
C3 C2 H2B 109.6(7) . . ?
H2A C2 H2B 111.9(10) . . ?
C4 C3 C2 102.38(5) . . ?
C4 C3 H3A 109.9(7) . . ?
C2 C3 H3A 115.6(7) . . ?
C4 C3 H3B 110.1(7) . . ?
C2 C3 H3B 109.9(7) . . ?
H3A C3 H3B 108.7(10) . . ?
O3 C4 O2 108.86(5) . . ?
O3 C4 C5 111.47(5) . . ?
O2 C4 C5 108.17(5) . . ?
O3 C4 C3 107.94(5) . . ?
O2 C4 C3 105.23(5) . . ?
C5 C4 C3 114.86(5) . . ?
O3 C5 C4 111.50(5) 3_667 . ?
O3 C5 H5A 109.0(7) 3_667 . ?
C4 C5 H5A 109.1(8) . . ?
O3 C5 H5B 106.3(6) 3_667 . ?
C4 C5 H5B 110.0(6) . . ?
H5A C5 H5B 110.8(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 178.14(6) . . . . ?
C4 O2 C1 C2 -1.60(7) . . . . ?
O1 C1 C2 C3 163.13(7) . . . . ?
O2 C1 C2 C3 -17.15(7) . . . . ?
C1 C2 C3 C4 27.59(7) . . . . ?
C5 O3 C4 O2 -65.93(6) 3_667 . . . ?
C5 O3 C4 C5 53.32(7) 3_667 . . . ?
C5 O3 C4 C3 -179.65(5) 3_667 . . . ?
C1 O2 C4 O3 -95.61(6) . . . . ?
C1 O2 C4 C5 143.11(5) . . . . ?
C1 O2 C4 C3 19.88(7) . . . . ?
C2 C3 C4 O3 86.91(6) . . . . ?
C2 C3 C4 O2 -29.21(7) . . . . ?
C2 C3 C4 C5 -148.06(6) . . . . ?
O3 C4 C5 O3 -52.38(7) . . . 3_667 ?
O2 C4 C5 O3 67.27(6) . . . 3_667 ?
C3 C4 C5 O3 -175.54(5) . . . 3_667 ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        38.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
