data_111
_audit_creation_date              2016-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common             ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety          'C18 H18 O5 S'
_chemical_formula_sum             'C18 H18 O5 S'
_chemical_formula_weight          346.38
_chemical_melting_point           ?
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       'triclinic'
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, -y, -z'

_cell_length_a                    9.8988(7)
_cell_length_b                    10.1507(7)
_cell_length_c                    10.2605(8)
_cell_angle_alpha                 111.653(2)
_cell_angle_beta                  95.303(2)
_cell_angle_gamma                 114.760(2)
_cell_volume                      832.05(10)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     7941
_cell_measurement_temperature     296(2)
_cell_measurement_theta_max       27.441
_cell_measurement_theta_min       3.590
_exptl_absorpt_coefficient_mu     0.219
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_correction_T_min   0.6459
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour             colorless
_exptl_crystal_density_diffrn     1.383
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_description        block
_exptl_crystal_F_000              364
_exptl_crystal_size_max           0.456
_exptl_crystal_size_mid           0.367
_exptl_crystal_size_min           0.113
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents   0.0408
_diffrn_reflns_av_unetI/netI      0.0289
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_number             17253
_diffrn_reflns_theta_full         27.54
_diffrn_reflns_theta_max          27.54
_diffrn_reflns_theta_min          3.02
_diffrn_ambient_temperature       296.15
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type   'CCD area detector'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_radiation_monochromator   'graphite'
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'fine-focus sealed tube'
_diffrn_standards_decay_%         ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_number          ?
_reflns_number_gt                 2931
_reflns_number_total              3824
_reflns_threshold_expression      >2sigma(I)
_computing_cell_refinement        'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection        ?
_computing_data_reduction         'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'XL (Sheldrick, 2008)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max          0.309
_refine_diff_density_min          -0.312
_refine_diff_density_rms          0.052
_refine_ls_extinction_coef        ?
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.017
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      221
_refine_ls_number_reflns          3824
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0662
_refine_ls_R_factor_gt            0.0477
_refine_ls_restrained_S_all       1.017
_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)+(0.0754P)²+0.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1223
_refine_ls_wR_factor_ref          0.1355
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C13(H13A,H13B,H13C)
;
_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
 S1 S 0.34858(5) 0.80653(5) 0.95125(6) 0.04763(17) Uani 1 d . . .
 O3 O 0.04044(14) 0.37503(14) 0.88140(13) 0.0433(3) Uani 1 d . . .
 O1 O -0.32742(15) 0.23027(16) 0.54706(14) 0.0504(3) Uani 1 d . . .
 O5 O -0.06209(17) 0.76895(16) 0.79629(16) 0.0531(4) Uani 1 d . . .
 C8 C 0.16930(19) 0.5200(2) 0.92302(19) 0.0375(4) Uani 1 d . . .
 O2 O -0.23246(18) 0.46887(18) 0.53910(16) 0.0614(4) Uani 1 d . . .
 C6 C 0.3082(2) 0.5789(2) 1.03229(19) 0.0381(4) Uani 1 d . . .
 O4 O 0.12773(18) 0.79230(19) 0.69000(19) 0.0624(4) Uani 1 d . . .
 C9 C 0.1728(2) 0.6263(2) 0.8710(2) 0.0394(4) Uani 1 d . . .
 C5 C 0.4173(2) 0.7364(2) 1.0592(2) 0.0422(4) Uani 1 d . . .
 C7 C 0.3461(2) 0.5046(2) 1.10891(19) 0.0418(4) Uani 1 d . . .
 H7 H 0.2741 0.4004 1.0918 0.050 Uiso 1 calc . . R
 C11 C -0.0818(2) 0.4351(2) 0.7056(2) 0.0396(4) Uani 1 d . . .
 C14 C -0.2192(2) 0.3846(2) 0.5906(2) 0.0442(4) Uani 1 d . . .
 C10 C 0.0359(2) 0.5887(2) 0.77009(19) 0.0391(4) Uani 1 d . . .
 C16 C 0.0376(2) 0.7251(2) 0.7435(2) 0.0431(4) Uani 1 d . . .
 C12 C -0.0647(2) 0.3067(2) 0.7371(2) 0.0422(4) Uani 1 d . . .
 H12 H -0.1675 0.2293 0.7341 0.051 Uiso 1 calc . . R
 C2 C 0.4902(2) 0.5852(2) 1.2100(2) 0.0469(4) Uani 1 d . . .
 C4 C 0.5637(2) 0.8181(2) 1.1597(2) 0.0515(5) Uani 1 d . . .
 H4 H 0.6370 0.9216 1.1765 0.062 Uiso 1 calc . . R
 C3 C 0.5967(2) 0.7419(3) 1.2331(2) 0.0536(5) Uani 1 d . . .
 H3 H 0.6939 0.7961 1.3012 0.064 Uiso 1 calc . . R
 C1 C 0.5330(3) 0.5078(3) 1.2941(2) 0.0600(6) Uani 1 d . . .
 H1A H 0.4531 0.4684 1.3379 0.090 Uiso 1 calc . . GR
 H1B H 0.6299 0.5867 1.3695 0.090 Uiso 1 calc . . GR
 H1C H 0.5435 0.4188 1.2287 0.090 Uiso 1 calc . . GR
 C15 C -0.4620(2) 0.1655(3) 0.4279(2) 0.0628(6) Uani 1 d . . .
 H15A H -0.4292 0.1835 0.3480 0.094 Uiso 1 calc . . GR
 H15B H -0.5215 0.2188 0.4604 0.094 Uiso 1 calc . . GR
 H15C H -0.5249 0.0509 0.3960 0.094 Uiso 1 calc . . GR
 C17 C -0.0723(4) 0.8942(3) 0.7664(3) 0.0786(8) Uani 1 d . . .
 H17A H -0.1080 0.8556 0.6614 0.094 Uiso 1 calc . . R
 H17B H 0.0294 0.9903 0.8049 0.094 Uiso 1 calc . . R
 C18 C -0.1820(3) 0.9345(3) 0.8363(3) 0.0812(8) Uani 1 d . . .
 H18A H -0.2817 0.8383 0.7996 0.122 Uiso 1 calc . . GR
 H18B H -0.1922 1.0146 0.8145 0.122 Uiso 1 calc . . GR
 H18C H -0.1439 0.9767 0.9406 0.122 Uiso 1 calc . . GR
 C13 C -0.0117(3) 0.2138(3) 0.6228(2) 0.0573(5) Uani 1 d . . .
 H13A H 0.0854 0.2880 0.6182 0.086 Uiso 1 calc . . GR
 H13B H -0.0884 0.1571 0.5291 0.086 Uiso 1 calc . . GR
 H13C H 0.0017 0.1370 0.6480 0.086 Uiso 1 calc . . GR


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 S1 C9 1.7350(18) . ?
 S1 C5 1.7448(19) . ?
 O3 C8 1.356(2) . ?
 O3 C12 1.452(2) . ?
 O1 C14 1.338(2) . ?
 O1 C15 1.440(2) . ?
 O5 C16 1.325(2) . ?
 O5 C17 1.453(2) . ?
 C8 C6 1.427(2) . ?
 C8 C9 1.359(2) . ?
 O2 C14 1.202(2) . ?
 C6 C5 1.404(2) . ?
 C6 C7 1.396(2) . ?
 O4 C16 1.191(2) . ?
 C9 C10 1.438(2) . ?
 C5 C4 1.392(3) . ?
 C7 H7 0.9300 . ?
 C7 C2 1.379(3) . ?
 C11 C14 1.475(3) . ?
 C11 C10 1.342(2) . ?
 C11 C12 1.522(2) . ?
 C10 C16 1.500(2) . ?
 C12 H12 0.9800 . ?
 C12 C13 1.500(3) . ?
 C2 C3 1.403(3) . ?
 C2 C1 1.501(3) . ?
 C4 H4 0.9300 . ?
 C4 C3 1.367(3) . ?
 C3 H3 0.9300 . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 0.9600 . ?
 C15 H15A 0.9600 . ?
 C15 H15B 0.9600 . ?
 C15 H15C 0.9600 . ?
 C17 H17A 0.9700 . ?
 C17 H17B 0.9700 . ?
 C17 C18 1.470(4) . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 0.9600 . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C9 S1 C5 90.56(8) . . ?
 C8 O3 C12 115.24(13) . . ?
 C14 O1 C15 115.99(16) . . ?
 C16 O5 C17 115.14(16) . . ?
 O3 C8 C6 123.04(15) . . ?
 O3 C8 C9 122.41(16) . . ?
 C9 C8 C6 114.40(15) . . ?
 C5 C6 C8 110.11(15) . . ?
 C7 C6 C8 130.27(16) . . ?
 C7 C6 C5 119.62(17) . . ?
 C8 C9 S1 112.36(14) . . ?
 C8 C9 C10 120.28(16) . . ?
 C10 C9 S1 127.15(13) . . ?
 C6 C5 S1 112.57(14) . . ?
 C4 C5 S1 126.72(15) . . ?
 C4 C5 C6 120.69(17) . . ?
 C6 C7 H7 119.9 . . ?
 C2 C7 C6 120.14(17) . . ?
 C2 C7 H7 119.9 . . ?
 C14 C11 C12 119.21(15) . . ?
 C10 C11 C14 120.73(15) . . ?
 C10 C11 C12 119.61(15) . . ?
 O1 C14 C11 111.59(15) . . ?
 O2 C14 O1 123.49(18) . . ?
 O2 C14 C11 124.90(18) . . ?
 C9 C10 C16 116.94(16) . . ?
 C11 C10 C9 117.91(15) . . ?
 C11 C10 C16 125.14(16) . . ?
 O5 C16 C10 112.58(15) . . ?
 O4 C16 O5 124.76(17) . . ?
 O4 C16 C10 122.45(17) . . ?
 O3 C12 C11 112.45(14) . . ?
 O3 C12 H12 107.7 . . ?
 O3 C12 C13 109.58(15) . . ?
 C11 C12 H12 107.7 . . ?
 C13 C12 C11 111.63(15) . . ?
 C13 C12 H12 107.7 . . ?
 C7 C2 C3 118.66(17) . . ?
 C7 C2 C1 120.99(19) . . ?
 C3 C2 C1 120.36(18) . . ?
 C5 C4 H4 120.9 . . ?
 C3 C4 C5 118.10(19) . . ?
 C3 C4 H4 120.9 . . ?
 C2 C3 H3 118.6 . . ?
 C4 C3 C2 122.78(19) . . ?
 C4 C3 H3 118.6 . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 O1 C15 H15A 109.5 . . ?
 O1 C15 H15B 109.5 . . ?
 O1 C15 H15C 109.5 . . ?
 H15A C15 H15B 109.5 . . ?
 H15A C15 H15C 109.5 . . ?
 H15B C15 H15C 109.5 . . ?
 O5 C17 H17A 109.9 . . ?
 O5 C17 H17B 109.9 . . ?
 O5 C17 C18 108.9(2) . . ?
 H17A C17 H17B 108.3 . . ?
 C18 C17 H17A 109.9 . . ?
 C18 C17 H17B 109.9 . . ?
 C17 C18 H18A 109.5 . . ?
 C17 C18 H18B 109.5 . . ?
 C17 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 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 . . ?

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
 S1 C9 C10 C11 171.51(14) . . . . ?
 S1 C9 C10 C16 -7.5(2) . . . . ?
 S1 C5 C4 C3 -179.26(15) . . . . ?
 O3 C8 C6 C5 -175.92(15) . . . . ?
 O3 C8 C6 C7 4.5(3) . . . . ?
 O3 C8 C9 S1 176.38(13) . . . . ?
 O3 C8 C9 C10 1.2(3) . . . . ?
 C8 O3 C12 C11 -39.9(2) . . . . ?
 C8 O3 C12 C13 84.88(18) . . . . ?
 C8 C6 C5 S1 -0.29(19) . . . . ?
 C8 C6 C5 C4 -178.62(16) . . . . ?
 C8 C6 C7 C2 179.28(17) . . . . ?
 C8 C9 C10 C11 -14.1(3) . . . . ?
 C8 C9 C10 C16 166.92(16) . . . . ?
 C6 C8 C9 S1 0.7(2) . . . . ?
 C6 C8 C9 C10 -174.47(15) . . . . ?
 C6 C5 C4 C3 -1.2(3) . . . . ?
 C6 C7 C2 C3 -0.3(3) . . . . ?
 C6 C7 C2 C1 179.68(16) . . . . ?
 C9 S1 C5 C6 0.57(14) . . . . ?
 C9 S1 C5 C4 178.77(18) . . . . ?
 C9 C8 C6 C5 -0.3(2) . . . . ?
 C9 C8 C6 C7 -179.83(17) . . . . ?
 C9 C10 C16 O5 -112.08(18) . . . . ?
 C9 C10 C16 O4 62.9(3) . . . . ?
 C5 S1 C9 C8 -0.71(14) . . . . ?
 C5 S1 C9 C10 174.05(17) . . . . ?
 C5 C6 C7 C2 -0.3(3) . . . . ?
 C5 C4 C3 C2 0.7(3) . . . . ?
 C7 C6 C5 S1 179.34(13) . . . . ?
 C7 C6 C5 C4 1.0(3) . . . . ?
 C7 C2 C3 C4 0.1(3) . . . . ?
 C11 C10 C16 O5 69.0(2) . . . . ?
 C11 C10 C16 O4 -116.0(2) . . . . ?
 C14 C11 C10 C9 -174.15(15) . . . . ?
 C14 C11 C10 C16 4.7(3) . . . . ?
 C14 C11 C12 O3 -159.38(15) . . . . ?
 C14 C11 C12 C13 77.0(2) . . . . ?
 C10 C11 C14 O1 -175.95(16) . . . . ?
 C10 C11 C14 O2 5.6(3) . . . . ?
 C10 C11 C12 O3 28.3(2) . . . . ?
 C10 C11 C12 C13 -95.4(2) . . . . ?
 C16 O5 C17 C18 -177.8(2) . . . . ?
 C12 O3 C8 C6 -157.72(16) . . . . ?
 C12 O3 C8 C9 27.0(2) . . . . ?
 C12 C11 C14 O1 11.8(2) . . . . ?
 C12 C11 C14 O2 -166.65(18) . . . . ?
 C12 C11 C10 C9 -1.9(3) . . . . ?
 C12 C11 C10 C16 176.98(16) . . . . ?
 C1 C2 C3 C4 -179.89(19) . . . . ?
 C15 O1 C14 O2 2.5(3) . . . . ?
 C15 O1 C14 C11 -175.92(16) . . . . ?
 C17 O5 C16 O4 8.6(3) . . . . ?
 C17 O5 C16 C10 -176.58(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
