data_stein1g
_audit_creation_date               2018-04-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

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. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C16 H18 O6 S'
_chemical_formula_sum              'C16 H18 O6 S'
_chemical_formula_weight           338.36
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C16 H18 O6 S'
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 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'
 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_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                     16.5505(3)
_cell_length_b                     10.3454(2)
_cell_length_c                     9.53748(17)
_cell_angle_alpha                  90
_cell_angle_beta                   101.3266(17)
_cell_angle_gamma                  90
_cell_volume                       1601.22(5)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6731
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        70.6020
_cell_measurement_theta_min        5.0370
_shelx_estimated_absorpt_T_max     0.941
_shelx_estimated_absorpt_T_min     0.506
_exptl_absorpt_coefficient_mu      2.059
_exptl_absorpt_correction_T_max    0.939
_exptl_absorpt_correction_T_min    0.620
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.404
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               712
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 -11 -1 0 0.0152
 11 1 0 0.0152
 0 -5 4 0.1115
 -3 5 4 0.1569
 -2 7 0 0.1134
 2 -7 0 0.1134
 1 4 -5 0.1178
 3 -2 -6 0.1789

_exptl_crystal_size_max            0.383
_exptl_crystal_size_mid            0.227
_exptl_crystal_size_min            0.03
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 -11.0000 -1.0000 -0.0000 0.5120 0.9222 -0.0139
 11.0000 1.0000 0.0000 -0.5120 -0.9222 0.0139
 0.0000 -5.0000 4.0000 0.2140 -0.1588 -0.9580
 -3.0000 5.0000 4.0000 -0.8431 0.5221 -0.1106
 -2.0000 7.0000 0.0000 -0.7436 0.4679 0.5925
 2.0000 -7.0000 -0.0000 0.7436 -0.4679 -0.5925
 1.0000 4.0000 -5.0000 -0.0414 0.0168 1.0048
 3.0000 -2.0000 -6.0000 0.6779 -0.4218 0.6311

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0374
_diffrn_reflns_av_unetI/netI       0.0246
_diffrn_reflns_Laue_measured_fraction_full  0.989
_diffrn_reflns_Laue_measured_fraction_max  0.989
_diffrn_reflns_limit_h_max         20
_diffrn_reflns_limit_h_min         -20
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              15126
_diffrn_reflns_point_group_measured_fraction_full  0.989
_diffrn_reflns_point_group_measured_fraction_max  0.989
_diffrn_reflns_theta_full          70.486
_diffrn_reflns_theta_max           70.486
_diffrn_reflns_theta_min           5.070
_diffrn_ambient_temperature        100.15
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.3756
_diffrn_detector_type              Atlas
_diffrn_measured_fraction_theta_full  0.989
_diffrn_measured_fraction_theta_max  0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -66.00  32.00   1.00    1.00    --  -42.08  37.00 150.00   98
  2  ω     23.00  98.00   1.00    1.00    --   42.08-125.00   0.00   75
  3  ω     23.00  98.00   1.00    1.00    --   42.08-125.00 120.00   75
  4  ω     71.00 172.00   1.00    2.00    --  100.00  61.00  30.00  101
  5  ω     74.00 173.00   1.00    2.00    --  100.00  45.00 150.00   99
  6  ω     74.00 173.00   1.00    2.00    --  100.00  45.00-180.00   99
  7  ω     28.00 129.00   1.00    2.00    --  100.00 -61.00-120.00  101
  8  ω     24.00 133.00   1.00    2.00    --  100.00 -77.00 -60.00  109
  9  ω     27.00 121.00   1.00    2.00    --  100.00-125.00 -90.00   94
 10  ω   -118.00 -10.00   1.00    1.00    --  -42.08 -76.00 -83.00  108
 11  ω   -118.00  -9.00   1.00    1.00    --  -42.08 -77.00  30.00  109
 12  ω   -118.00  -9.00   1.00    1.00    --  -42.08 -77.00 150.00  109
 13  ω     71.00 172.00   1.00    2.00    --  100.00  61.00  90.00  101
 14  ω     71.00 172.00   1.00    2.00    --  100.00  61.00-120.00  101
 15  ω     24.00  67.00   1.00    2.00    --  100.00 -77.00  60.00   43
 16  ω     71.00 172.00   1.00    2.00    --  100.00  61.00 -60.00  101
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.0359529000
_diffrn_orient_matrix_UB_12        -0.1165045000
_diffrn_orient_matrix_UB_13        -0.0921210000
_diffrn_orient_matrix_UB_21        -0.0876365000
_diffrn_orient_matrix_UB_22        0.0418044000
_diffrn_orient_matrix_UB_23        0.0125481000
_diffrn_orient_matrix_UB_31        -0.0062697000
_diffrn_orient_matrix_UB_32        0.0828522000
_diffrn_orient_matrix_UB_33        -0.1359293000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'micro-focus sealed X-ray tube'
_diffrn_source_type                'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2639
_reflns_number_total               3033
_reflns_odcompleteness_completeness  99.97
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       66.97
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection         'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction          'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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      'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max           0.282
_refine_diff_density_min           -0.315
_refine_diff_density_rms           0.050
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       213
_refine_ls_number_reflns           3033
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0414
_refine_ls_R_factor_gt             0.0341
_refine_ls_restrained_S_all        1.043
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0453P)²+0.7654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0852
_refine_ls_wR_factor_ref           0.0903
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 S1 S 0.30234(2) 0.46478(4) 0.61798(4) 0.01941(12) Uani 1 1 d . . . . .
 O1 O 0.26838(7) 0.56440(11) 0.50974(13) 0.0248(3) Uani 1 1 d . . . . .
 O2 O 0.22483(7) 0.10959(11) 0.65802(12) 0.0221(3) Uani 1 1 d . . . . .
 O3 O 0.08586(7) 0.34832(11) 0.67239(13) 0.0254(3) Uani 1 1 d . . . . .
 O4 O 0.17073(7) 0.51764(12) 0.74700(13) 0.0248(3) Uani 1 1 d . . . . .
 O5 O 0.53610(8) 0.38540(12) 0.29283(14) 0.0296(3) Uani 1 1 d . . . . .
 O6 O 0.56285(7) 0.17303(12) 0.31616(13) 0.0268(3) Uani 1 1 d . . . . .
 C1 C 0.22655(10) 0.34742(16) 0.64560(17) 0.0196(3) Uani 1 1 d . . . . .
 C2 C 0.25167(10) 0.22471(16) 0.62397(17) 0.0189(3) Uani 1 1 d . . . . .
 C3 C 0.32351(10) 0.21947(16) 0.55448(17) 0.0189(3) Uani 1 1 d . . . . .
 C4 C 0.36012(10) 0.11163(16) 0.50642(17) 0.0207(3) Uani 1 1 d . . . . .
 H4 H 0.341421 0.027040 0.522181 0.025 Uiso 1 1 calc R . . . .
 C5 C 0.42475(10) 0.13018(16) 0.43475(17) 0.0213(3) Uani 1 1 d . . . . .
 H5 H 0.450268 0.057563 0.400651 0.026 Uiso 1 1 calc R . . . .
 C6 C 0.45250(10) 0.25491(16) 0.41244(17) 0.0201(3) Uani 1 1 d . . . . .
 C7 C 0.41686(10) 0.36311(16) 0.46403(17) 0.0207(3) Uani 1 1 d . . . . .
 H7 H 0.436060 0.447893 0.450639 0.025 Uiso 1 1 calc R . . . .
 C8 C 0.35304(10) 0.34272(16) 0.53487(17) 0.0196(3) Uani 1 1 d . . . . .
 C9 C 0.15252(10) 0.39994(16) 0.69074(17) 0.0208(3) Uani 1 1 d . . . . .
 C10 C 0.52054(10) 0.27993(17) 0.33371(18) 0.0216(4) Uani 1 1 d . . . . .
 C11 C 0.16648(11) 0.10218(17) 0.75255(19) 0.0248(4) Uani 1 1 d . . . . .
 H11A H 0.111051 0.121504 0.698691 0.037 Uiso 1 1 calc GR . . . .
 H11B H 0.181542 0.165078 0.830116 0.037 Uiso 1 1 calc GR . . . .
 H11C H 0.167337 0.014946 0.792860 0.037 Uiso 1 1 calc GR . . . .
 C12 C 0.63183(11) 0.19219(19) 0.2453(2) 0.0304(4) Uani 1 1 d . . . . .
 H12A H 0.612213 0.231525 0.151304 0.046 Uiso 1 1 calc GR . . . .
 H12B H 0.657549 0.108634 0.233351 0.046 Uiso 1 1 calc GR . . . .
 H12C H 0.672363 0.249357 0.303357 0.046 Uiso 1 1 calc GR . . . .
 C13 C 0.10571(11) 0.60644(16) 0.77782(19) 0.0243(4) Uani 1 1 d . . . . .
 C14 C 0.15281(14) 0.7309(2) 0.8151(3) 0.0439(6) Uani 1 1 d . . . . .
 H14A H 0.197560 0.716602 0.897523 0.066 Uiso 1 1 calc GR . . . .
 H14B H 0.115487 0.797474 0.838604 0.066 Uiso 1 1 calc GR . . . .
 H14C H 0.175916 0.759448 0.733180 0.066 Uiso 1 1 calc GR . . . .
 C15 C 0.03874(13) 0.62512(19) 0.6452(2) 0.0325(4) Uani 1 1 d . . . . .
 H15A H 0.064179 0.643482 0.562850 0.049 Uiso 1 1 calc GR . . . .
 H15B H 0.003354 0.697657 0.660400 0.049 Uiso 1 1 calc GR . . . .
 H15C H 0.005537 0.546248 0.626973 0.049 Uiso 1 1 calc GR . . . .
 C16 C 0.07199(12) 0.55383(19) 0.90277(19) 0.0297(4) Uani 1 1 d . . . . .
 H16A H 0.043076 0.472309 0.875068 0.045 Uiso 1 1 calc GR . . . .
 H16B H 0.033542 0.616490 0.930403 0.045 Uiso 1 1 calc GR . . . .
 H16C H 0.117500 0.538620 0.983771 0.045 Uiso 1 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 O1 1.4887(12) . ?
 S1 C1 1.8019(16) . ?
 S1 C8 1.7855(17) . ?
 O2 C2 1.3334(19) . ?
 O2 C11 1.4468(19) . ?
 O3 C9 1.207(2) . ?
 O4 C9 1.341(2) . ?
 O4 C13 1.487(2) . ?
 O5 C10 1.203(2) . ?
 O6 C10 1.337(2) . ?
 O6 C12 1.450(2) . ?
 C1 C2 1.364(2) . ?
 C1 C9 1.479(2) . ?
 C2 C3 1.471(2) . ?
 C3 C4 1.390(2) . ?
 C3 C8 1.391(2) . ?
 C4 C5 1.391(2) . ?
 C5 C6 1.400(2) . ?
 C6 C7 1.399(2) . ?
 C6 C10 1.494(2) . ?
 C7 C8 1.377(2) . ?
 C13 C14 1.511(3) . ?
 C13 C15 1.522(3) . ?
 C13 C16 1.513(2) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 O1 S1 C1 112.90(7) . . ?
 O1 S1 C8 109.15(7) . . ?
 C8 S1 C1 89.41(8) . . ?
 C2 O2 C11 119.62(13) . . ?
 C9 O4 C13 121.69(13) . . ?
 C10 O6 C12 115.15(14) . . ?
 C2 C1 S1 111.30(12) . . ?
 C2 C1 C9 132.86(15) . . ?
 C9 C1 S1 115.80(12) . . ?
 O2 C2 C1 131.94(15) . . ?
 O2 C2 C3 114.46(14) . . ?
 C1 C2 C3 113.56(14) . . ?
 C4 C3 C2 128.42(15) . . ?
 C4 C3 C8 120.27(15) . . ?
 C8 C3 C2 111.28(14) . . ?
 C3 C4 C5 118.59(15) . . ?
 C4 C5 C6 120.58(16) . . ?
 C5 C6 C10 122.58(15) . . ?
 C7 C6 C5 120.70(15) . . ?
 C7 C6 C10 116.73(15) . . ?
 C8 C7 C6 117.84(15) . . ?
 C3 C8 S1 112.36(12) . . ?
 C7 C8 S1 125.59(13) . . ?
 C7 C8 C3 121.99(15) . . ?
 O3 C9 O4 125.95(15) . . ?
 O3 C9 C1 125.51(15) . . ?
 O4 C9 C1 108.42(14) . . ?
 O5 C10 O6 123.97(16) . . ?
 O5 C10 C6 123.40(16) . . ?
 O6 C10 C6 112.62(14) . . ?
 O4 C13 C14 102.30(14) . . ?
 O4 C13 C15 110.57(14) . . ?
 O4 C13 C16 109.06(14) . . ?
 C14 C13 C15 110.18(17) . . ?
 C14 C13 C16 111.99(16) . . ?
 C16 C13 C15 112.28(15) . . ?


_olex2_date_sample_data_collection  2018-04-16
_olex2_date_sample_submission      2018-04-16
_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.545
_oxdiff_exptl_absorpt_empirical_full_min  0.734
