# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_galiso1obzstol
_database_code_depnum_ccdc_archive 'CCDC 1052154'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 O6 S'
_chemical_formula_sum            'C23 H26 O6 S'
_chemical_formula_weight         430.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.8253(7)
_cell_length_b                   8.3302(5)
_cell_length_c                   42.609(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2067.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1715
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.5120
_cell_measurement_theta_min      2.4860
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             912
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.119
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            5054
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.91
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   59.00  120.50   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega   39.00   84.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512   57.0000 -180.0000 60

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   15.00   0.7500   40.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -77.0000  120.0000 80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0018008000
_diffrn_orient_matrix_UB_12      -0.0000043000
_diffrn_orient_matrix_UB_13      0.0166499000
_diffrn_orient_matrix_UB_21      0.1024046000
_diffrn_orient_matrix_UB_22      -0.0459963000
_diffrn_orient_matrix_UB_23      -0.0002319000
_diffrn_orient_matrix_UB_31      0.0657836000
_diffrn_orient_matrix_UB_32      0.0716428000
_diffrn_orient_matrix_UB_33      -0.0001231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3210
_reflns_number_total             3465
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0161P)²+3.0903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1103
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2) = Uanis(C7) = Uanis(C6)
Uanis(C18) = Uanis(C19) = Uanis(C20) = Uanis(C21) = Uanis(C22) = Uanis(C23)
Uanis(C12) = Uanis(C17)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.4879(8) -0.3382(5) -0.54205(8) 0.0241(10) Uani 1 d . . .
H1A H -0.3530 -0.3228 -0.5546 0.036 Uiso 1 calc . . GR
H1B H -0.5458 -0.2358 -0.5354 0.036 Uiso 1 calc . . GR
H1C H -0.6029 -0.3926 -0.5542 0.036 Uiso 1 calc . . GR
C2 C -0.4284(7) -0.4377(5) -0.51368(7) 0.0157(3) Uani 1 d . . .
C3 C -0.2239(7) -0.5222(4) -0.51154(7) 0.0157(3) Uani 1 d . . .
H3 H -0.1163 -0.5134 -0.5276 0.019 Uiso 1 calc . . R
C4 C -0.1768(7) -0.6199(5) -0.48585(7) 0.0157(3) Uani 1 d . . .
H4 H -0.0372 -0.6737 -0.4846 0.019 Uiso 1 calc . . R
C5 C -0.3380(7) -0.6373(5) -0.46188(7) 0.0157(3) Uani 1 d . . .
C6 C -0.5443(7) -0.5523(5) -0.46367(7) 0.0157(3) Uani 1 d . . .
H6 H -0.6532 -0.5621 -0.4478 0.019 Uiso 1 calc . . R
C7 C -0.5858(7) -0.4530(5) -0.48928(7) 0.0157(3) Uani 1 d . . .
H7 H -0.7224 -0.3954 -0.4901 0.019 Uiso 1 calc . . R
C8 C -0.4419(6) -0.7131(5) -0.39921(7) 0.0122(7) Uani 1 d . . .
H8 H -0.4603 -0.5964 -0.4008 0.015 Uiso 1 calc . . R
C9 C -0.6794(6) -0.7895(5) -0.39625(7) 0.0138(8) Uani 1 d . . .
H9 H -0.7439 -0.8079 -0.4172 0.017 Uiso 1 calc . . R
C10 C -0.6789(6) -0.9464(4) -0.37770(7) 0.0144(8) Uani 1 d . . .
H10 H -0.8371 -0.9812 -0.3738 0.017 Uiso 1 calc . . R
C11 C -0.5474(6) -0.9351(5) -0.34634(8) 0.0129(8) Uani 1 d . . .
H11 H -0.6534 -0.9463 -0.3286 0.015 Uiso 1 calc . . R
C12 C -0.4617(6) -1.1732(5) -0.37170(7) 0.0124(6) Uani 1 d . . .
C13 C -0.6388(7) -1.2905(5) -0.35965(8) 0.0186(8) Uani 1 d . . .
H13A H -0.7632 -1.2326 -0.3502 0.028 Uiso 1 calc . . GR
H13B H -0.5696 -1.3599 -0.3443 0.028 Uiso 1 calc . . GR
H13C H -0.6961 -1.3537 -0.3768 0.028 Uiso 1 calc . . GR
C14 C -0.2540(6) -1.2541(5) -0.38567(8) 0.0184(8) Uani 1 d . . .
H14A H -0.2989 -1.3143 -0.4039 0.028 Uiso 1 calc . . GR
H14B H -0.1874 -1.3252 -0.3705 0.028 Uiso 1 calc . . GR
H14C H -0.1433 -1.1743 -0.3916 0.028 Uiso 1 calc . . GR
C15 C -0.4133(6) -0.7792(5) -0.34375(7) 0.0124(8) Uani 1 d . . .
H15 H -0.5183 -0.6905 -0.3391 0.015 Uiso 1 calc . . R
C16 C -0.2308(6) -0.7892(4) -0.31875(7) 0.0130(7) Uani 1 d . . .
H16A H -0.2928 -0.8389 -0.3000 0.016 Uiso 1 calc . . R
H16B H -0.1031 -0.8537 -0.3261 0.016 Uiso 1 calc . . R
C17 C 0.0507(6) -0.6177(5) -0.29700(7) 0.0124(6) Uani 1 d . . .
C18 C 0.1071(6) -0.4475(5) -0.28909(7) 0.0141(3) Uani 1 d . . .
C19 C 0.3202(6) -0.4165(5) -0.27586(7) 0.0141(3) Uani 1 d . . .
H19 H 0.4232 -0.5000 -0.2725 0.017 Uiso 1 calc . . R
C20 C 0.3796(6) -0.2608(5) -0.26760(7) 0.0141(3) Uani 1 d . . .
H20 H 0.5220 -0.2402 -0.2586 0.017 Uiso 1 calc . . R
C21 C 0.2270(6) -0.1358(5) -0.27279(7) 0.0141(3) Uani 1 d . . .
H21 H 0.2676 -0.0313 -0.2675 0.017 Uiso 1 calc . . R
C22 C 0.0135(6) -0.1669(5) -0.28593(7) 0.0141(3) Uani 1 d . . .
H22 H -0.0904 -0.0835 -0.2889 0.017 Uiso 1 calc . . R
C23 C -0.0453(7) -0.3226(5) -0.29463(7) 0.0141(3) Uani 1 d . . .
H23 H -0.1862 -0.3429 -0.3041 0.017 Uiso 1 calc . . R
O1 O -0.2946(4) -0.7479(3) -0.37301(5) 0.0132(6) Uani 1 d . . .
O2 O -0.8174(4) -0.6759(3) -0.37970(6) 0.0175(6) Uani 1 d . . .
H2 H -0.9531 -0.7005 -0.3814 0.026 Uiso 1 calc . . GR
O3 O -0.5583(4) -1.0677(3) -0.39476(5) 0.0151(6) Uani 1 d . . .
O4 O -0.3892(5) -1.0669(3) -0.34709(5) 0.0145(6) Uani 1 d . . .
O5 O -0.1542(4) -0.6287(3) -0.31182(5) 0.0132(6) Uani 1 d . . .
O6 O 0.1683(4) -0.7317(3) -0.29072(5) 0.0165(6) Uani 1 d . . .
S1 S -0.27549(16) -0.78293(11) -0.432693(18) 0.0144(2) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.506(5) . ?
C2 C3 1.386(6) . ?
C2 C7 1.392(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(5) . ?
C5 C6 1.397(5) . ?
C5 S1 1.775(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.528(5) . ?
C8 O1 1.438(4) . ?
C8 S1 1.820(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.528(5) . ?
C9 O2 1.428(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.543(5) . ?
C10 O3 1.429(4) . ?
C11 H11 0.9800 . ?
C11 C15 1.520(5) . ?
C11 O4 1.434(4) . ?
C12 C13 1.511(5) . ?
C12 C14 1.508(5) . ?
C12 O3 1.434(4) . ?
C12 O4 1.436(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.507(4) . ?
C15 O1 1.449(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 O5 1.440(4) . ?
C17 C18 1.494(5) . ?
C17 O5 1.354(4) . ?
C17 O6 1.201(4) . ?
C18 C19 1.388(5) . ?
C18 C23 1.388(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(5) . ?
C23 H23 0.9300 . ?
O2 H2 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 122.0(3) . . ?
C3 C2 C7 118.1(3) . . ?
C7 C2 C1 119.9(4) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 S1 116.5(3) . . ?
C6 C5 S1 124.1(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.7(4) . . ?
C6 C7 H7 119.1 . . ?
C9 C8 H8 108.7 . . ?
C9 C8 S1 114.4(2) . . ?
O1 C8 H8 108.7 . . ?
O1 C8 C9 113.1(3) . . ?
O1 C8 S1 103.1(2) . . ?
S1 C8 H8 108.7 . . ?
C8 C9 H9 109.7 . . ?
C10 C9 C8 113.4(3) . . ?
C10 C9 H9 109.7 . . ?
O2 C9 C8 105.9(3) . . ?
O2 C9 H9 109.7 . . ?
O2 C9 C10 108.2(3) . . ?
C9 C10 H10 109.8 . . ?
C9 C10 C11 113.4(3) . . ?
C11 C10 H10 109.8 . . ?
O3 C10 C9 110.0(3) . . ?
O3 C10 H10 109.8 . . ?
O3 C10 C11 103.9(3) . . ?
C10 C11 H11 110.4 . . ?
C15 C11 C10 111.7(3) . . ?
C15 C11 H11 110.4 . . ?
O4 C11 C10 104.7(3) . . ?
O4 C11 H11 110.4 . . ?
O4 C11 C15 109.0(3) . . ?
C14 C12 C13 113.2(3) . . ?
O3 C12 C13 111.2(3) . . ?
O3 C12 C14 108.6(3) . . ?
O3 C12 O4 103.7(3) . . ?
O4 C12 C13 110.6(3) . . ?
O4 C12 C14 109.1(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15 109.7 . . ?
C16 C15 C11 111.5(3) . . ?
C16 C15 H15 109.7 . . ?
O1 C15 C11 109.7(3) . . ?
O1 C15 H15 109.7 . . ?
O1 C15 C16 106.3(3) . . ?
C15 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
O5 C16 C15 108.2(3) . . ?
O5 C16 H16A 110.1 . . ?
O5 C16 H16B 110.1 . . ?
O5 C17 C18 111.3(3) . . ?
O6 C17 C18 125.1(3) . . ?
O6 C17 O5 123.6(3) . . ?
C19 C18 C17 117.7(4) . . ?
C19 C18 C23 120.1(4) . . ?
C23 C18 C17 122.2(3) . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.9(4) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.1(4) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 119.7(3) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C8 O1 C15 114.8(2) . . ?
C9 O2 H2 109.5 . . ?
C10 O3 C12 106.1(2) . . ?
C11 O4 C12 107.4(3) . . ?
C17 O5 C16 115.6(3) . . ?
C5 S1 C8 102.78(17) . . ?

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
C1 C2 C3 C4 -176.8(4) . . . . ?
C1 C2 C7 C6 175.6(4) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C2 C7 C6 -1.4(6) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C3 C4 C5 S1 172.6(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C4 C5 S1 C8 156.5(3) . . . . ?
C5 C6 C7 C2 1.1(6) . . . . ?
C6 C5 S1 C8 -29.6(4) . . . . ?
C7 C2 C3 C4 0.1(6) . . . . ?
C8 C9 C10 C11 48.2(4) . . . . ?
C8 C9 C10 O3 -67.6(4) . . . . ?
C9 C8 O1 C15 -27.2(4) . . . . ?
C9 C8 S1 C5 94.2(3) . . . . ?
C9 C10 C11 C15 -10.0(4) . . . . ?
C9 C10 C11 O4 -127.8(3) . . . . ?
C9 C10 O3 C12 150.4(3) . . . . ?
C10 C11 C15 C16 -162.2(3) . . . . ?
C10 C11 C15 O1 -44.7(4) . . . . ?
C10 C11 O4 C12 -15.0(3) . . . . ?
C11 C10 O3 C12 28.8(3) . . . . ?
C11 C15 C16 O5 -164.9(3) . . . . ?
C11 C15 O1 C8 67.1(4) . . . . ?
C13 C12 O3 C10 80.2(3) . . . . ?
C13 C12 O4 C11 -86.4(3) . . . . ?
C14 C12 O3 C10 -154.6(3) . . . . ?
C14 C12 O4 C11 148.5(3) . . . . ?
C15 C11 O4 C12 -134.6(3) . . . . ?
C15 C16 O5 C17 -161.6(3) . . . . ?
C16 C15 O1 C8 -172.1(3) . . . . ?
C17 C18 C19 C20 -178.9(3) . . . . ?
C17 C18 C23 C22 178.1(3) . . . . ?
C18 C17 O5 C16 -176.4(3) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C19 C18 C23 C22 -2.1(5) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 -1.6(5) . . . . ?
C21 C22 C23 C18 2.3(5) . . . . ?
C23 C18 C19 C20 1.2(5) . . . . ?
O1 C8 C9 C10 -29.9(4) . . . . ?
O1 C8 C9 O2 88.6(3) . . . . ?
O1 C8 S1 C5 -142.6(2) . . . . ?
O1 C15 C16 O5 75.6(3) . . . . ?
O2 C9 C10 C11 -69.0(4) . . . . ?
O2 C9 C10 O3 175.2(3) . . . . ?
O3 C10 C11 C15 109.4(3) . . . . ?
O3 C10 C11 O4 -8.4(3) . . . . ?
O3 C12 O4 C11 32.9(3) . . . . ?
O4 C11 C15 C16 -47.1(3) . . . . ?
O4 C11 C15 O1 70.5(3) . . . . ?
O4 C12 O3 C10 -38.7(3) . . . . ?
O5 C17 C18 C19 -175.4(3) . . . . ?
O5 C17 C18 C23 4.5(4) . . . . ?
O6 C17 C18 C19 5.8(5) . . . . ?
O6 C17 C18 C23 -174.3(3) . . . . ?
O6 C17 O5 C16 2.5(5) . . . . ?
S1 C5 C6 C7 -173.3(3) . . . . ?
S1 C8 C9 C10 87.7(3) . . . . ?
S1 C8 C9 O2 -153.8(2) . . . . ?
S1 C8 O1 C15 -151.3(2) . . . . ?

_olex2_date_sample_data_collection 2015-01-15
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_stol1
_database_code_depnum_ccdc_archive 'CCDC 1052160'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H18 O5 S'
_chemical_formula_sum            'C13 H18 O5 S'
_chemical_formula_weight         286.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 O5 H18 S1'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.1361(3)
_cell_length_b                   8.6117(5)
_cell_length_c                   15.7890(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.403(5)
_cell_angle_gamma                90.00
_cell_volume                     694.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    291.85(10)
_cell_measurement_theta_max      27.3120
_cell_measurement_theta_min      2.5870
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.218
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2594
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   34.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   57.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega   31.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -99.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -38.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
  4 omega   81.00  107.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  178.0000 -150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0070328000
_diffrn_orient_matrix_UB_12      -0.0105628000
_diffrn_orient_matrix_UB_13      0.0442439000
_diffrn_orient_matrix_UB_21      -0.1341924000
_diffrn_orient_matrix_UB_22      0.0214835000
_diffrn_orient_matrix_UB_23      -0.0055641000
_diffrn_orient_matrix_UB_31      -0.0355321000
_diffrn_orient_matrix_UB_32      -0.0787774000
_diffrn_orient_matrix_UB_33      -0.0074677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1725
_reflns_number_total             1812
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.0605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0856
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3a), O4(H4a), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.0902(8) -0.8997(6) -0.6093(2) 0.0747(13) Uani 1 d . . .
H1A H -0.2128 -0.8397 -0.6463 0.112 Uiso 1 calc . . GR
H1B H -0.0680 -0.9998 -0.6343 0.112 Uiso 1 calc . . GR
H1C H 0.0753 -0.8468 -0.6017 0.112 Uiso 1 calc . . GR
C2 C -0.1934(6) -0.9199(4) -0.52337(17) 0.0461(8) Uani 1 d . . .
C3 C -0.0823(6) -0.8376(4) -0.45170(19) 0.0485(8) Uani 1 d . . .
H3 H 0.0590 -0.7720 -0.4567 0.058 Uiso 1 calc . . R
C4 C -0.1795(6) -0.8520(4) -0.37284(17) 0.0417(7) Uani 1 d . . .
H4 H -0.1045 -0.7952 -0.3263 0.050 Uiso 1 calc . . R
C5 C -0.3874(5) -0.9508(4) -0.36408(14) 0.0349(6) Uani 1 d . . .
C6 C -0.5001(6) -1.0351(4) -0.43447(19) 0.0476(8) Uani 1 d . . .
H6 H -0.6406 -1.1012 -0.4293 0.057 Uiso 1 calc . . R
C7 C -0.3994(7) -1.0189(4) -0.51284(18) 0.0524(9) Uani 1 d . . .
H7 H -0.4732 -1.0765 -0.5592 0.063 Uiso 1 calc . . R
C8 C -0.3136(5) -1.0912(3) -0.20062(16) 0.0314(6) Uani 1 d . . .
H8 H -0.1315 -1.0711 -0.2103 0.038 Uiso 1 calc . . R
C9 C -0.3502(5) -1.0598(3) -0.10657(16) 0.0302(6) Uani 1 d . . .
H9 H -0.5373 -1.0623 -0.0995 0.036 Uiso 1 calc . . R
C10 C -0.2061(5) -1.1823(3) -0.04855(15) 0.0310(6) Uani 1 d . . .
H10 H -0.0169 -1.1684 -0.0492 0.037 Uiso 1 calc . . R
C11 C -0.2805(5) -1.3455(3) -0.07994(15) 0.0306(6) Uani 1 d . . .
H11 H -0.1753 -1.4223 -0.0455 0.037 Uiso 1 calc . . R
C12 C -0.2316(5) -1.3608(3) -0.17377(16) 0.0323(6) Uani 1 d . . .
H12 H -0.0451 -1.3443 -0.1786 0.039 Uiso 1 calc . . R
C13 C -0.3137(6) -1.5187(3) -0.21133(17) 0.0372(6) Uani 1 d . . .
H13A H -0.4950 -1.5395 -0.2033 0.045 Uiso 1 calc . . R
H13B H -0.2978 -1.5197 -0.2720 0.045 Uiso 1 calc . . R
O1 O -0.3838(4) -1.2467(2) -0.22493(10) 0.0354(5) Uani 1 d . . .
O2 O -0.2483(4) -0.9077(2) -0.08617(12) 0.0426(5) Uani 1 d . . .
H2 H -0.3145 -0.8735 -0.0451 0.064 Uiso 1 calc . . GR
O3 O -0.2705(4) -1.1590(2) 0.03727(10) 0.0375(5) Uani 1 d . . .
H3A H -0.1362 -1.1623 0.0706 0.056 Uiso 1 calc . . GR
O4 O -0.5530(4) -1.3666(2) -0.07023(13) 0.0392(5) Uani 1 d . . .
H4A H -0.5844 -1.4595 -0.0663 0.059 Uiso 1 calc . . GR
O5 O -0.1472(5) -1.6354(3) -0.16907(14) 0.0511(6) Uani 1 d . . .
H5 H -0.2328 -1.7143 -0.1632 0.077 Uiso 1 calc . . GR
S1 S -0.53223(14) -0.95967(9) -0.26561(4) 0.0434(2) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.521(4) . ?
C2 C3 1.402(4) . ?
C2 C7 1.383(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.398(4) . ?
C5 S1 1.798(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.541(3) . ?
C8 O1 1.428(3) . ?
C8 S1 1.828(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.533(4) . ?
C9 O2 1.434(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.525(4) . ?
C10 O3 1.444(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.536(3) . ?
C11 O4 1.436(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.524(4) . ?
C12 O1 1.445(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O5 1.435(4) . ?
O2 H2 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?
O5 H5 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C1 121.7(3) . . ?
C7 C2 C3 117.6(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 S1 120.7(2) . . ?
C6 C5 S1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 122.0(3) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C9 C8 H8 109.9 . . ?
C9 C8 S1 107.40(17) . . ?
O1 C8 H8 109.9 . . ?
O1 C8 C9 111.7(2) . . ?
O1 C8 S1 108.04(17) . . ?
S1 C8 H8 109.9 . . ?
C8 C9 H9 109.4 . . ?
C10 C9 C8 110.6(2) . . ?
C10 C9 H9 109.4 . . ?
O2 C9 C8 107.2(2) . . ?
O2 C9 H9 109.4 . . ?
O2 C9 C10 110.8(2) . . ?
C9 C10 H10 108.8 . . ?
C11 C10 C9 110.7(2) . . ?
C11 C10 H10 108.8 . . ?
O3 C10 C9 108.6(2) . . ?
O3 C10 H10 108.8 . . ?
O3 C10 C11 111.0(2) . . ?
C10 C11 H11 109.8 . . ?
C10 C11 C12 109.3(2) . . ?
C12 C11 H11 109.8 . . ?
O4 C11 C10 107.1(2) . . ?
O4 C11 H11 109.8 . . ?
O4 C11 C12 111.01(19) . . ?
C11 C12 H12 109.3 . . ?
C13 C12 C11 112.6(2) . . ?
C13 C12 H12 109.3 . . ?
O1 C12 C11 110.1(2) . . ?
O1 C12 H12 109.3 . . ?
O1 C12 C13 106.27(19) . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
O5 C13 C12 108.6(2) . . ?
O5 C13 H13A 110.0 . . ?
O5 C13 H13B 110.0 . . ?
C8 O1 C12 112.51(19) . . ?
C9 O2 H2 109.5 . . ?
C10 O3 H3A 109.5 . . ?
C11 O4 H4A 109.5 . . ?
C13 O5 H5 109.5 . . ?
C5 S1 C8 102.96(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
C1 C2 C3 C4 178.3(3) . . . . ?
C1 C2 C7 C6 -178.3(3) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C2 C7 C6 1.5(5) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 S1 -175.0(2) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C4 C5 S1 C8 -82.5(2) . . . . ?
C5 C6 C7 C2 -1.1(5) . . . . ?
C6 C5 S1 C8 102.8(2) . . . . ?
C7 C2 C3 C4 -1.4(5) . . . . ?
C8 C9 C10 C11 -51.4(3) . . . . ?
C8 C9 C10 O3 -173.5(2) . . . . ?
C9 C8 O1 C12 -58.8(3) . . . . ?
C9 C8 S1 C5 158.46(18) . . . . ?
C9 C10 C11 C12 54.4(3) . . . . ?
C9 C10 C11 O4 -65.9(2) . . . . ?
C10 C11 C12 C13 -177.3(2) . . . . ?
C10 C11 C12 O1 -58.8(3) . . . . ?
C11 C12 C13 O5 -65.9(3) . . . . ?
C11 C12 O1 C8 61.9(3) . . . . ?
C13 C12 O1 C8 -175.8(2) . . . . ?
O1 C8 C9 C10 52.9(3) . . . . ?
O1 C8 C9 O2 173.8(2) . . . . ?
O1 C8 S1 C5 -80.95(19) . . . . ?
O1 C12 C13 O5 173.5(2) . . . . ?
O2 C9 C10 C11 -170.2(2) . . . . ?
O2 C9 C10 O3 67.8(3) . . . . ?
O3 C10 C11 C12 175.04(19) . . . . ?
O3 C10 C11 O4 54.7(2) . . . . ?
O4 C11 C12 C13 -59.3(3) . . . . ?
O4 C11 C12 O1 59.1(3) . . . . ?
S1 C5 C6 C7 175.2(2) . . . . ?
S1 C8 C9 C10 171.19(18) . . . . ?
S1 C8 C9 O2 -67.9(2) . . . . ?
S1 C8 O1 C12 -176.74(16) . . . . ?

_olex2_date_sample_data_collection 2014-11-16
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_galisostol
_database_code_depnum_ccdc_archive 'CCDC 1411666'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C16 H22 O5 S), H2 O'
_chemical_formula_sum            'C32 H46 O11 S2'
_chemical_formula_weight         670.81
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   11.1679(7)
_cell_length_b                   7.7832(5)
_cell_length_c                   19.3582(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.192(7)
_cell_angle_gamma                90.00
_cell_volume                     1656.09(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1752
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      25.6110
_cell_measurement_theta_min      1.9550
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7119
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00  107.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3556   57.0000   90.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega   50.00   78.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.7031   57.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   21.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -27.9494  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   62.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3556  -99.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega  -15.00   11.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3556  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -29.00   96.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       29.3556   38.0000 -120.0000 125

#__ type_ start__ end____ width___ exp.time_
  7 omega   22.00   47.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -        0.7031   57.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0058643000
_diffrn_orient_matrix_UB_12      -0.0032744000
_diffrn_orient_matrix_UB_13      0.0358616000
_diffrn_orient_matrix_UB_21      -0.0642180000
_diffrn_orient_matrix_UB_22      -0.0020070000
_diffrn_orient_matrix_UB_23      -0.0099439000
_diffrn_orient_matrix_UB_31      0.0015789000
_diffrn_orient_matrix_UB_32      -0.0911027000
_diffrn_orient_matrix_UB_33      -0.0009961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4377
_reflns_number_total             5384
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0353P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1213
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C24(H24), C25(H25), C26(H26),
 C30(H30), C31(H31)
2.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C32(H32A,H32B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C19(H19), C20(H20), C22(H22), C23(H23)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O7(H7A), O10(H10A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C -0.2853(5) -0.7334(8) 0.1166(2) 0.0400(14) Uani 1 d . . .
H1A H -0.3236 -0.6440 0.1409 0.060 Uiso 1 calc . . GR
H1B H -0.1978 -0.7108 0.1220 0.060 Uiso 1 calc . . GR
H1C H -0.2984 -0.8458 0.1368 0.060 Uiso 1 calc . . GR
C2 C -0.3409(4) -0.7327(7) 0.0398(2) 0.0271(12) Uani 1 d . . .
C3 C -0.4500(5) -0.8165(7) 0.0160(3) 0.0276(12) Uani 1 d . . .
H3 H -0.4912 -0.8725 0.0486 0.033 Uiso 1 calc . . R
C4 C -0.4998(4) -0.8196(6) -0.0550(3) 0.0238(11) Uani 1 d . . .
H4 H -0.5730 -0.8810 -0.0710 0.029 Uiso 1 calc . . R
C5 C -0.4426(4) -0.7333(6) -0.1022(2) 0.0192(10) Uani 1 d . . .
C6 C -0.3356(4) -0.6460(6) -0.0795(3) 0.0230(12) Uani 1 d . . .
H6 H -0.2969 -0.5848 -0.1119 0.028 Uiso 1 calc . . R
C7 C -0.2854(5) -0.6486(6) -0.0088(3) 0.0253(12) Uani 1 d . . .
H7 H -0.2105 -0.5909 0.0068 0.030 Uiso 1 calc . . R
C8 C -0.3944(4) -0.7439(7) -0.2406(2) 0.0210(10) Uani 1 d . . .
H8 H -0.3169 -0.7772 -0.2093 0.025 Uiso 1 calc . . R
C9 C -0.4245(4) -0.8724(6) -0.3002(3) 0.0221(11) Uani 1 d . . .
H9 H -0.5109 -0.8558 -0.3238 0.027 Uiso 1 calc . . R
C10 C -0.3418(4) -0.8582(6) -0.3544(2) 0.0201(11) Uani 1 d . . .
H10 H -0.2678 -0.9307 -0.3394 0.024 Uiso 1 calc . . R
C11 C -0.4495(4) -0.7619(6) -0.4623(2) 0.0205(10) Uani 1 d . . .
C12 C -0.5865(4) -0.7572(7) -0.4718(2) 0.0258(11) Uani 1 d . . .
H12A H -0.6172 -0.6583 -0.5010 0.039 Uiso 1 calc . . GR
H12B H -0.6112 -0.7470 -0.4259 0.039 Uiso 1 calc . . GR
H12C H -0.6201 -0.8632 -0.4948 0.039 Uiso 1 calc . . GR
C13 C -0.4042(4) -0.7621(7) -0.5311(2) 0.0229(11) Uani 1 d . . .
H13A H -0.4310 -0.8674 -0.5570 0.034 Uiso 1 calc . . GR
H13B H -0.3151 -0.7569 -0.5222 0.034 Uiso 1 calc . . GR
H13C H -0.4370 -0.6620 -0.5589 0.034 Uiso 1 calc . . GR
C14 C -0.3030(4) -0.6764(6) -0.3689(2) 0.0200(11) Uani 1 d . . .
H14 H -0.2275 -0.6803 -0.3900 0.024 Uiso 1 calc . . R
C15 C -0.2827(4) -0.5603(6) -0.3053(2) 0.0207(11) Uani 1 d . . .
H15 H -0.2068 -0.5971 -0.2733 0.025 Uiso 1 calc . . R
C16 C -0.2693(4) -0.3761(6) -0.3252(2) 0.0221(11) Uani 1 d . . .
H16A H -0.2121 -0.3685 -0.3588 0.027 Uiso 1 calc . . R
H16B H -0.3492 -0.3316 -0.3489 0.027 Uiso 1 calc . . R
O1 O -0.3838(3) -0.5729(4) -0.26794(17) 0.0208(8) Uani 1 d . . .
O2 O -0.4103(3) -1.0421(4) -0.27110(17) 0.0241(8) Uani 1 d . . .
H2 H -0.4789 -1.0826 -0.2682 0.036 Uiso 1 calc . . GR
O3 O -0.4024(3) -0.9123(4) -0.42240(16) 0.0222(8) Uani 1 d . . .
O4 O -0.4016(3) -0.6174(4) -0.41955(17) 0.0225(8) Uani 1 d . . .
O5 O -0.2253(3) -0.2728(4) -0.26509(16) 0.0238(8) Uani 1 d . . .
H5 H -0.2767 -0.1965 -0.2609 0.036 Uiso 1 calc . . GR
S1 S -0.51709(10) -0.73920(17) -0.19153(6) 0.0245(3) Uani 1 d . . .
C17 C -0.2792(5) -0.1628(7) -1.0997(3) 0.0292(13) Uani 1 d . . .
H17A H -0.2527 -0.2176 -1.1400 0.044 Uiso 1 calc . . GR
H17B H -0.2785 -0.0377 -1.1054 0.044 Uiso 1 calc . . GR
H17C H -0.3619 -0.2008 -1.0969 0.044 Uiso 1 calc . . GR
C18 C -0.1941(4) -0.2124(6) -1.0334(2) 0.0243(12) Uani 1 d . . .
C19 C -0.0892(4) -0.3034(6) -1.0351(3) 0.0265(12) Uani 1 d . . .
H19 H -0.0680 -0.3314 -1.0791 0.032 Uiso 1 calc . . R
C20 C -0.0132(4) -0.3556(6) -0.9737(3) 0.0253(12) Uani 1 d . . .
H20 H 0.0585 -0.4194 -0.9759 0.030 Uiso 1 calc . . R
C21 C -0.0433(4) -0.3133(6) -0.9092(2) 0.0208(11) Uani 1 d . . .
C22 C -0.1443(4) -0.2144(6) -0.9066(2) 0.0264(12) Uani 1 d . . .
H22 H -0.1624 -0.1789 -0.8627 0.032 Uiso 1 calc . . R
C23 C -0.2195(4) -0.1666(6) -0.9684(3) 0.0248(12) Uani 1 d . . .
H23 H -0.2903 -0.1008 -0.9661 0.030 Uiso 1 calc . . R
C24 C -0.0528(4) -0.4068(7) -0.7724(2) 0.0222(11) Uani 1 d . . .
H24 H -0.1358 -0.4337 -0.7991 0.027 Uiso 1 calc . . R
C25 C -0.0172(4) -0.5433(6) -0.7158(3) 0.0208(11) Uani 1 d . . .
H25 H 0.0647 -0.5151 -0.6880 0.025 Uiso 1 calc . . R
C26 C -0.1110(4) -0.5460(6) -0.6670(2) 0.0196(11) Uani 1 d . . .
H26 H -0.1851 -0.6104 -0.6896 0.024 Uiso 1 calc . . R
C27 C -0.0256(4) -0.4858(6) -0.5500(3) 0.0211(11) Uani 1 d . . .
C28 C 0.1085(4) -0.4942(6) -0.5224(3) 0.0244(12) Uani 1 d . . .
H28A H 0.1321 -0.3985 -0.4900 0.037 Uiso 1 calc . . GR
H28B H 0.1530 -0.4865 -0.5616 0.037 Uiso 1 calc . . GR
H28C H 0.1279 -0.6033 -0.4976 0.037 Uiso 1 calc . . GR
C29 C -0.1017(4) -0.4965(6) -0.4932(2) 0.0244(12) Uani 1 d . . .
H29A H -0.0876 -0.6073 -0.4691 0.037 Uiso 1 calc . . GR
H29B H -0.1879 -0.4860 -0.5142 0.037 Uiso 1 calc . . GR
H29C H -0.0790 -0.4032 -0.4595 0.037 Uiso 1 calc . . GR
C30 C -0.1464(4) -0.3679(6) -0.6459(2) 0.0214(11) Uani 1 d . . .
H30 H -0.2248 -0.3748 -0.6279 0.026 Uiso 1 calc . . R
C31 C -0.1571(4) -0.2332(6) -0.7032(2) 0.0195(10) Uani 1 d . . .
H31 H -0.2332 -0.2559 -0.7377 0.023 Uiso 1 calc . . R
C32 C -0.1624(4) -0.0514(6) -0.6763(2) 0.0213(11) Uani 1 d . . .
H32A H -0.2204 -0.0457 -0.6431 0.026 Uiso 1 calc . . R
H32B H -0.0812 -0.0171 -0.6508 0.026 Uiso 1 calc . . R
O6 O -0.0557(3) -0.2428(4) -0.73931(15) 0.0214(7) Uani 1 d . . .
O7 O -0.0142(3) -0.7106(4) -0.74480(17) 0.0238(8) Uani 1 d . . .
H7A H 0.0583 -0.7391 -0.7449 0.036 Uiso 1 calc . . GR
O8 O -0.0617(3) -0.6226(4) -0.60075(17) 0.0232(8) Uani 1 d . . .
O9 O -0.0501(3) -0.3292(4) -0.58917(16) 0.0208(8) Uani 1 d . . .
O10 O -0.2001(3) 0.0636(4) -0.73322(17) 0.0247(8) Uani 1 d . . .
H10A H -0.1402 0.1215 -0.7406 0.037 Uiso 1 calc . . GR
S2 S 0.05203(11) -0.39731(17) -0.83270(7) 0.0252(3) Uani 1 d . . .
O11 O -0.5717(3) -0.2961(4) -0.2751(2) 0.0418(10) Uani 1 d . . .
H11A H -0.5190 -0.3757 -0.2671 0.063 Uiso 1 d . . G
H11B H -0.6412 -0.3357 -0.2714 0.063 Uiso 1 d . . G


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.507(6) . ?
C2 C3 1.387(7) . ?
C2 C7 1.379(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(6) . ?
C5 C6 1.377(6) . ?
C5 S1 1.782(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(6) . ?
C7 H7 0.9500 . ?
C8 H8 1.0000 . ?
C8 C9 1.517(6) . ?
C8 O1 1.445(6) . ?
C8 S1 1.801(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.520(6) . ?
C9 O2 1.434(5) . ?
C10 H10 1.0000 . ?
C10 C14 1.520(6) . ?
C10 O3 1.434(5) . ?
C11 C12 1.509(6) . ?
C11 C13 1.506(6) . ?
C11 O3 1.449(5) . ?
C11 O4 1.442(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.511(6) . ?
C14 O4 1.416(5) . ?
C15 H15 1.0000 . ?
C15 C16 1.499(6) . ?
C15 O1 1.447(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 O5 1.429(5) . ?
O2 H2 0.8400 . ?
O5 H5 0.8400 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C18 1.506(6) . ?
C18 C19 1.375(6) . ?
C18 C23 1.384(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(6) . ?
C21 C22 1.374(6) . ?
C21 S2 1.787(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(6) . ?
C23 H23 0.9500 . ?
C24 H24 1.0000 . ?
C24 C25 1.527(7) . ?
C24 O6 1.432(6) . ?
C24 S2 1.795(5) . ?
C25 H25 1.0000 . ?
C25 C26 1.531(6) . ?
C25 O7 1.420(6) . ?
C26 H26 1.0000 . ?
C26 C30 1.517(6) . ?
C26 O8 1.433(5) . ?
C27 C28 1.499(6) . ?
C27 C29 1.506(6) . ?
C27 O8 1.457(5) . ?
C27 O9 1.436(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30 1.0000 . ?
C30 C31 1.515(6) . ?
C30 O9 1.426(5) . ?
C31 H31 1.0000 . ?
C31 C32 1.512(6) . ?
C31 O6 1.435(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 O10 1.424(5) . ?
O7 H7A 0.8400 . ?
O10 H10A 0.8400 . ?
O11 H11A 0.8501 . ?
O11 H11B 0.8500 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.7(5) . . ?
C7 C2 C1 121.2(5) . . ?
C7 C2 C3 118.1(4) . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 S1 116.0(4) . . ?
C6 C5 S1 123.5(4) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.0(5) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 121.9(5) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 H8 110.0 . . ?
C9 C8 S1 109.1(3) . . ?
O1 C8 H8 110.0 . . ?
O1 C8 C9 110.5(4) . . ?
O1 C8 S1 107.1(3) . . ?
S1 C8 H8 110.0 . . ?
C8 C9 H9 109.2 . . ?
C8 C9 C10 113.3(4) . . ?
C10 C9 H9 109.2 . . ?
O2 C9 C8 108.4(4) . . ?
O2 C9 H9 109.2 . . ?
O2 C9 C10 107.4(4) . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C14 115.0(4) . . ?
C14 C10 H10 109.3 . . ?
O3 C10 C9 111.5(4) . . ?
O3 C10 H10 109.3 . . ?
O3 C10 C14 102.0(4) . . ?
C13 C11 C12 112.6(4) . . ?
O3 C11 C12 110.4(4) . . ?
O3 C11 C13 108.9(4) . . ?
O4 C11 C12 108.5(4) . . ?
O4 C11 C13 111.1(4) . . ?
O4 C11 O3 105.2(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14 109.6 . . ?
C15 C14 C10 114.4(4) . . ?
C15 C14 H14 109.6 . . ?
O4 C14 C10 102.5(4) . . ?
O4 C14 H14 109.6 . . ?
O4 C14 C15 110.9(4) . . ?
C14 C15 H15 108.8 . . ?
C16 C15 C14 111.7(4) . . ?
C16 C15 H15 108.8 . . ?
O1 C15 C14 110.4(4) . . ?
O1 C15 H15 108.8 . . ?
O1 C15 C16 108.4(4) . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O5 C16 C15 111.3(4) . . ?
O5 C16 H16A 109.4 . . ?
O5 C16 H16B 109.4 . . ?
C8 O1 C15 111.6(3) . . ?
C9 O2 H2 109.5 . . ?
C10 O3 C11 108.6(3) . . ?
C14 O4 C11 108.0(3) . . ?
C16 O5 H5 109.5 . . ?
C5 S1 C8 104.2(2) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 C23 117.8(5) . . ?
C23 C18 C17 120.6(4) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.4(5) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 S2 117.1(3) . . ?
C22 C21 C20 119.7(4) . . ?
C22 C21 S2 123.2(4) . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.7(5) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 121.7(5) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 H24 109.0 . . ?
C25 C24 S2 112.2(3) . . ?
O6 C24 H24 109.0 . . ?
O6 C24 C25 108.8(4) . . ?
O6 C24 S2 108.8(3) . . ?
S2 C24 H24 109.0 . . ?
C24 C25 H25 109.3 . . ?
C24 C25 C26 109.4(4) . . ?
C26 C25 H25 109.3 . . ?
O7 C25 C24 112.1(4) . . ?
O7 C25 H25 109.3 . . ?
O7 C25 C26 107.3(4) . . ?
C25 C26 H26 109.9 . . ?
C30 C26 C25 113.1(4) . . ?
C30 C26 H26 109.9 . . ?
O8 C26 C25 111.2(4) . . ?
O8 C26 H26 109.9 . . ?
O8 C26 C30 102.5(4) . . ?
C28 C27 C29 113.2(4) . . ?
O8 C27 C28 110.4(4) . . ?
O8 C27 C29 109.1(4) . . ?
O9 C27 C28 108.1(4) . . ?
O9 C27 C29 110.7(4) . . ?
O9 C27 O8 105.1(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30 109.3 . . ?
C31 C30 C26 115.2(4) . . ?
C31 C30 H30 109.3 . . ?
O9 C30 C26 101.7(3) . . ?
O9 C30 H30 109.3 . . ?
O9 C30 C31 111.6(4) . . ?
C30 C31 H31 108.4 . . ?
C32 C31 C30 113.5(4) . . ?
C32 C31 H31 108.4 . . ?
O6 C31 C30 110.7(4) . . ?
O6 C31 H31 108.4 . . ?
O6 C31 C32 107.4(4) . . ?
C31 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
O10 C32 C31 110.2(4) . . ?
O10 C32 H32A 109.6 . . ?
O10 C32 H32B 109.6 . . ?
C24 O6 C31 110.3(3) . . ?
C25 O7 H7A 109.5 . . ?
C26 O8 C27 108.4(3) . . ?
C30 O9 C27 106.0(3) . . ?
C32 O10 H10A 109.5 . . ?
C21 S2 C24 101.1(2) . . ?
H11A O11 H11B 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
C1 C2 C3 C4 -178.4(5) . . . . ?
C1 C2 C7 C6 -179.6(5) . . . . ?
C2 C3 C4 C5 -2.4(7) . . . . ?
C3 C2 C7 C6 0.1(7) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C3 C4 C5 S1 -177.8(4) . . . . ?
C4 C5 C6 C7 1.1(7) . . . . ?
C4 C5 S1 C8 -145.4(4) . . . . ?
C5 C6 C7 C2 -1.6(7) . . . . ?
C6 C5 S1 C8 35.9(5) . . . . ?
C7 C2 C3 C4 1.8(7) . . . . ?
C8 C9 C10 C14 -36.0(6) . . . . ?
C8 C9 C10 O3 -151.5(4) . . . . ?
C9 C8 O1 C15 -64.4(4) . . . . ?
C9 C8 S1 C5 137.6(3) . . . . ?
C9 C10 C14 C15 35.5(6) . . . . ?
C9 C10 C14 O4 -84.6(5) . . . . ?
C9 C10 O3 C11 96.7(4) . . . . ?
C10 C14 C15 C16 -168.6(4) . . . . ?
C10 C14 C15 O1 -47.9(5) . . . . ?
C10 C14 O4 C11 -33.3(4) . . . . ?
C12 C11 O3 C10 -109.6(4) . . . . ?
C12 C11 O4 C14 135.4(4) . . . . ?
C13 C11 O3 C10 126.3(4) . . . . ?
C13 C11 O4 C14 -100.4(4) . . . . ?
C14 C10 O3 C11 -26.6(4) . . . . ?
C14 C15 C16 O5 -167.8(4) . . . . ?
C14 C15 O1 C8 63.3(5) . . . . ?
C15 C14 O4 C11 -155.8(4) . . . . ?
C16 C15 O1 C8 -174.1(4) . . . . ?
O1 C8 C9 C10 49.5(5) . . . . ?
O1 C8 C9 O2 168.6(3) . . . . ?
O1 C8 S1 C5 -102.7(3) . . . . ?
O1 C15 C16 O5 70.4(5) . . . . ?
O2 C9 C10 C14 -155.7(4) . . . . ?
O2 C9 C10 O3 88.8(4) . . . . ?
O3 C10 C14 C15 156.4(4) . . . . ?
O3 C10 C14 O4 36.3(4) . . . . ?
O3 C11 O4 C14 17.3(4) . . . . ?
O4 C11 O3 C10 7.2(4) . . . . ?
O4 C14 C15 C16 -53.2(5) . . . . ?
O4 C14 C15 O1 67.4(5) . . . . ?
S1 C5 C6 C7 179.7(4) . . . . ?
S1 C8 C9 C10 167.1(3) . . . . ?
S1 C8 C9 O2 -73.8(4) . . . . ?
S1 C8 O1 C15 176.8(3) . . . . ?
C17 C18 C19 C20 -177.2(5) . . . . ?
C17 C18 C23 C22 178.4(5) . . . . ?
C18 C19 C20 C21 -0.7(7) . . . . ?
C19 C18 C23 C22 -1.8(7) . . . . ?
C19 C20 C21 C22 -2.9(7) . . . . ?
C19 C20 C21 S2 175.6(4) . . . . ?
C20 C21 C22 C23 4.0(7) . . . . ?
C20 C21 S2 C24 -152.7(4) . . . . ?
C21 C22 C23 C18 -1.7(7) . . . . ?
C22 C21 S2 C24 25.7(5) . . . . ?
C23 C18 C19 C20 3.0(7) . . . . ?
C24 C25 C26 C30 -44.3(5) . . . . ?
C24 C25 C26 O8 -159.0(4) . . . . ?
C25 C24 O6 C31 -70.4(4) . . . . ?
C25 C24 S2 C21 154.1(4) . . . . ?
C25 C26 C30 C31 38.1(6) . . . . ?
C25 C26 C30 O9 -82.8(4) . . . . ?
C25 C26 O8 C27 100.0(4) . . . . ?
C26 C30 C31 C32 -166.2(4) . . . . ?
C26 C30 C31 O6 -45.3(5) . . . . ?
C26 C30 O9 C27 -39.7(4) . . . . ?
C28 C27 O8 C26 -118.8(4) . . . . ?
C28 C27 O9 C30 145.0(4) . . . . ?
C29 C27 O8 C26 116.2(4) . . . . ?
C29 C27 O9 C30 -90.5(4) . . . . ?
C30 C26 O8 C27 -21.1(4) . . . . ?
C30 C31 C32 O10 -166.7(4) . . . . ?
C30 C31 O6 C24 61.6(5) . . . . ?
C31 C30 O9 C27 -163.1(4) . . . . ?
C32 C31 O6 C24 -174.0(3) . . . . ?
O6 C24 C25 C26 60.2(5) . . . . ?
O6 C24 C25 O7 179.1(3) . . . . ?
O6 C24 S2 C21 -85.4(3) . . . . ?
O6 C31 C32 O10 70.6(5) . . . . ?
O7 C25 C26 C30 -166.2(4) . . . . ?
O7 C25 C26 O8 79.1(4) . . . . ?
O8 C26 C30 C31 157.9(4) . . . . ?
O8 C26 C30 O9 37.0(4) . . . . ?
O8 C27 O9 C30 27.1(4) . . . . ?
O9 C27 O8 C26 -2.5(5) . . . . ?
O9 C30 C31 C32 -50.8(5) . . . . ?
O9 C30 C31 O6 70.1(5) . . . . ?
S2 C21 C22 C23 -174.4(4) . . . . ?
S2 C24 C25 C26 -179.3(3) . . . . ?
S2 C24 C25 O7 -60.4(5) . . . . ?
S2 C24 O6 C31 167.0(3) . . . . ?

_olex2_date_sample_data_collection 2015-03-11
_olex2_submission_special_instructions 'No special instructions were received'
