data_190510e
_audit_creation_date               2019-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C18 H21 N O5 S, H2 O'
_chemical_formula_sum              'C18 H23 N O6 S'
_chemical_formula_weight           381.43
_chemical_absolute_configuration   S
_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'
 'N' 'N' 0.0061 0.0033 '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'

_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             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     8.1162(7)
_cell_length_b                     11.0214(9)
_cell_length_c                     10.5496(8)
_cell_angle_alpha                  90
_cell_angle_beta                   91.170(2)
_cell_angle_gamma                  90
_cell_volume                       943.48(13)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      1726
_cell_measurement_temperature      298(2)
_cell_measurement_theta_max        21.643
_cell_measurement_theta_min        2.51
_shelx_estimated_absorpt_T_max     0.972
_shelx_estimated_absorpt_T_min     0.941
_exptl_absorpt_coefficient_mu      0.205
_exptl_absorpt_correction_T_max    0.9718
_exptl_absorpt_correction_T_min    0.9410
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     sadabs
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.343
_exptl_crystal_density_meas        1.343
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               404
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.25
_exptl_crystal_size_min            0.14
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0245
_diffrn_reflns_av_unetI/netI       0.0610
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.975
_diffrn_reflns_limit_h_max         6
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         14
_diffrn_reflns_limit_k_min         -14
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              6059
_diffrn_reflns_point_group_measured_fraction_full  0.865
_diffrn_reflns_point_group_measured_fraction_max  0.819
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           28.686
_diffrn_reflns_theta_min           2.510
_diffrn_ambient_temperature        298.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.975
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.601
_reflns_Friedel_fraction_full      0.718
_reflns_Friedel_fraction_max       0.647
_reflns_number_gt                  2335
_reflns_number_total               3984
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SMART'
_computing_data_collection         'Bruker SMART'
_computing_data_reduction          'Bruker SAINT'
_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      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.232
_refine_diff_density_min           -0.257
_refine_diff_density_rms           0.039
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.06(12)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       239
_refine_ls_number_reflns           3984
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.1036
_refine_ls_R_factor_gt             0.0502
_refine_ls_restrained_S_all        1.024
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0403P)²+0.0189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0886
_refine_ls_wR_factor_ref           0.1054
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.94(12)
 0.06(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 N1(H1), O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17)
3.e Tetrahedral OH refined with riding coordinates:
 O1(H1A)
3.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       ?
_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
 N1 N 0.2153(4) 0.9250(3) 0.8627(3) 0.0525(9) Uani 1 1 d . . . . .
 H1 H 0.191803 0.849046 0.857617 0.063 Uiso 1 1 d R . . . .
 O1 O 0.2986(4) 0.5045(3) 0.7442(2) 0.0615(8) Uani 1 1 d . . . . .
 H1A H 0.262041 0.467684 0.804985 0.092 Uiso 1 1 calc R . . . .
 O2 O 0.2332(4) 0.6644(3) 0.8608(3) 0.0585(8) Uani 1 1 d . . . . .
 O3 O 0.3176(5) 0.6765(3) 0.3167(3) 0.0812(10) Uani 1 1 d . . . . .
 O4 O -0.0801(4) 0.9438(3) 0.8350(3) 0.0675(8) Uani 1 1 d . . . . .
 O5 O 0.0901(4) 1.1256(3) 0.8726(3) 0.0805(10) Uani 1 1 d . . . . .
 O6 O 0.1655(5) 0.3674(3) 0.9143(3) 0.1090(15) Uani 1 1 d . . . . .
 H6A H 0.139255 0.387939 0.988919 0.131 Uiso 1 1 d R . . . .
 H6B H 0.141365 0.293019 0.903760 0.131 Uiso 1 1 d R . . . .
 S1 S 0.06804(14) 1.00974(9) 0.81427(10) 0.0562(3) Uani 1 1 d . . . . .
 C1 C 0.2902(5) 0.6229(4) 0.7656(4) 0.0499(10) Uani 1 1 d . . . . .
 C2 C 0.3545(5) 0.6971(3) 0.6586(3) 0.0454(10) Uani 1 1 d . . . . .
 C3 C 0.4406(5) 0.8052(4) 0.6798(4) 0.0474(10) Uani 1 1 d . . . . .
 C4 C 0.4856(6) 0.8697(4) 0.5731(4) 0.0579(11) Uani 1 1 d . . . . .
 H4 H 0.543875 0.941716 0.584087 0.070 Uiso 1 1 calc R . . . .
 C5 C 0.4476(6) 0.8319(4) 0.4517(4) 0.0597(12) Uani 1 1 d . . . . .
 H5 H 0.478977 0.878346 0.382665 0.072 Uiso 1 1 calc R . . . .
 C6 C 0.3631(6) 0.7251(4) 0.4331(4) 0.0578(11) Uani 1 1 d . . . . .
 C7 C 0.3169(5) 0.6580(4) 0.5367(4) 0.0513(10) Uani 1 1 d . . . . .
 H7 H 0.259724 0.585621 0.524608 0.062 Uiso 1 1 calc R . . . .
 C8 C 0.4902(5) 0.8536(4) 0.8086(4) 0.0581(11) Uani 1 1 d . . . . .
 H8A H 0.604906 0.878169 0.806956 0.070 Uiso 1 1 calc R . . . .
 H8B H 0.481115 0.788844 0.870293 0.070 Uiso 1 1 calc R . . . .
 C9 C 0.3870(5) 0.9611(4) 0.8517(4) 0.0523(11) Uani 1 1 d . . . . .
 H9 H 0.392799 1.024373 0.786688 0.063 Uiso 1 1 calc R . . . .
 C10 C 0.4520(6) 1.0141(5) 0.9762(4) 0.0780(14) Uani 1 1 d . . . . .
 H10A H 0.384495 1.081570 0.999983 0.117 Uiso 1 1 calc GR . . . .
 H10B H 0.563431 1.041042 0.966100 0.117 Uiso 1 1 calc GR . . . .
 H10C H 0.449018 0.953113 1.041106 0.117 Uiso 1 1 calc GR . . . .
 C11 C 0.3395(8) 0.7481(5) 0.2081(4) 0.0953(18) Uani 1 1 d . . . . .
 H11A H 0.282635 0.823857 0.217618 0.143 Uiso 1 1 calc GR . . . .
 H11B H 0.296077 0.706173 0.135009 0.143 Uiso 1 1 calc GR . . . .
 H11C H 0.454909 0.763323 0.197434 0.143 Uiso 1 1 calc GR . . . .
 C12 C 0.0891(5) 1.0323(3) 0.6497(4) 0.0493(10) Uani 1 1 d . . . . .
 C13 C 0.0406(6) 0.9431(4) 0.5667(5) 0.0603(11) Uani 1 1 d . . . . .
 H13 H -0.006155 0.871799 0.596355 0.072 Uiso 1 1 calc R . . . .
 C14 C 0.0619(6) 0.9602(4) 0.4384(5) 0.0644(12) Uani 1 1 d . . . . .
 H14 H 0.026281 0.900202 0.382224 0.077 Uiso 1 1 calc R . . . .
 C15 C 0.1342(5) 1.0635(5) 0.3911(4) 0.0620(12) Uani 1 1 d . . . . .
 C16 C 0.1852(6) 1.1508(4) 0.4777(5) 0.0670(13) Uani 1 1 d . . . . .
 H16 H 0.236046 1.220820 0.448685 0.080 Uiso 1 1 calc R . . . .
 C17 C 0.1622(6) 1.1363(4) 0.6058(5) 0.0616(12) Uani 1 1 d . . . . .
 H17 H 0.195895 1.196497 0.662393 0.074 Uiso 1 1 calc R . . . .
 C18 C 0.1614(7) 1.0816(6) 0.2515(5) 0.0890(16) Uani 1 1 d . . . . .
 H18A H 0.275004 1.066855 0.233292 0.134 Uiso 1 1 calc GR . . . .
 H18B H 0.133221 1.163442 0.228506 0.134 Uiso 1 1 calc GR . . . .
 H18C H 0.093122 1.026217 0.203832 0.134 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
 N1 H1 0.8603 . ?
 N1 S1 1.593(3) . ?
 N1 C9 1.456(5) . ?
 O1 H1A 0.8200 . ?
 O1 C1 1.326(5) . ?
 O2 C1 1.205(5) . ?
 O3 C6 1.383(5) . ?
 O3 C11 1.405(6) . ?
 O4 S1 1.426(3) . ?
 O5 S1 1.427(3) . ?
 O6 H6A 0.8500 . ?
 O6 H6B 0.8502 . ?
 S1 C12 1.766(4) . ?
 C1 C2 1.496(5) . ?
 C2 C3 1.397(5) . ?
 C2 C7 1.384(5) . ?
 C3 C4 1.387(5) . ?
 C3 C8 1.507(5) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.375(6) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.374(6) . ?
 C6 C7 1.378(5) . ?
 C7 H7 0.9300 . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C8 C9 1.525(6) . ?
 C9 H9 0.9800 . ?
 C9 C10 1.522(5) . ?
 C10 H10A 0.9600 . ?
 C10 H10B 0.9600 . ?
 C10 H10C 0.9600 . ?
 C11 H11A 0.9600 . ?
 C11 H11B 0.9600 . ?
 C11 H11C 0.9600 . ?
 C12 C13 1.369(6) . ?
 C12 C17 1.374(5) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.380(6) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.379(6) . ?
 C15 C16 1.384(6) . ?
 C15 C18 1.506(7) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.378(6) . ?
 C17 H17 0.9300 . ?
 C18 H18A 0.9600 . ?
 C18 H18B 0.9600 . ?
 C18 H18C 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
 S1 N1 H1 112.7 . . ?
 C9 N1 H1 118.2 . . ?
 C9 N1 S1 121.8(3) . . ?
 C1 O1 H1A 109.5 . . ?
 C6 O3 C11 118.1(4) . . ?
 H6A O6 H6B 108.4 . . ?
 N1 S1 C12 108.11(18) . . ?
 O4 S1 N1 106.38(18) . . ?
 O4 S1 O5 119.3(2) . . ?
 O4 S1 C12 108.74(19) . . ?
 O5 S1 N1 107.41(19) . . ?
 O5 S1 C12 106.52(19) . . ?
 O1 C1 C2 112.9(4) . . ?
 O2 C1 O1 122.5(4) . . ?
 O2 C1 C2 124.6(4) . . ?
 C3 C2 C1 121.8(3) . . ?
 C7 C2 C1 117.2(4) . . ?
 C7 C2 C3 121.0(3) . . ?
 C2 C3 C8 124.8(3) . . ?
 C4 C3 C2 116.5(4) . . ?
 C4 C3 C8 118.7(4) . . ?
 C3 C4 H4 118.6 . . ?
 C5 C4 C3 122.9(4) . . ?
 C5 C4 H4 118.6 . . ?
 C4 C5 H5 120.2 . . ?
 C6 C5 C4 119.6(4) . . ?
 C6 C5 H5 120.2 . . ?
 C5 C6 O3 125.6(4) . . ?
 C5 C6 C7 119.3(4) . . ?
 C7 C6 O3 115.1(4) . . ?
 C2 C7 H7 119.6 . . ?
 C6 C7 C2 120.7(4) . . ?
 C6 C7 H7 119.6 . . ?
 C3 C8 H8A 108.8 . . ?
 C3 C8 H8B 108.8 . . ?
 C3 C8 C9 113.9(3) . . ?
 H8A C8 H8B 107.7 . . ?
 C9 C8 H8A 108.8 . . ?
 C9 C8 H8B 108.8 . . ?
 N1 C9 C8 110.1(3) . . ?
 N1 C9 H9 108.0 . . ?
 N1 C9 C10 110.5(3) . . ?
 C8 C9 H9 108.0 . . ?
 C10 C9 C8 111.9(4) . . ?
 C10 C9 H9 108.0 . . ?
 C9 C10 H10A 109.5 . . ?
 C9 C10 H10B 109.5 . . ?
 C9 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 O3 C11 H11A 109.5 . . ?
 O3 C11 H11B 109.5 . . ?
 O3 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 C13 C12 S1 119.7(3) . . ?
 C13 C12 C17 120.2(4) . . ?
 C17 C12 S1 120.0(3) . . ?
 C12 C13 H13 120.4 . . ?
 C12 C13 C14 119.3(4) . . ?
 C14 C13 H13 120.4 . . ?
 C13 C14 H14 119.0 . . ?
 C15 C14 C13 122.0(4) . . ?
 C15 C14 H14 119.0 . . ?
 C14 C15 C16 117.3(4) . . ?
 C14 C15 C18 122.4(5) . . ?
 C16 C15 C18 120.3(5) . . ?
 C15 C16 H16 119.3 . . ?
 C17 C16 C15 121.5(4) . . ?
 C17 C16 H16 119.3 . . ?
 C12 C17 C16 119.7(4) . . ?
 C12 C17 H17 120.2 . . ?
 C16 C17 H17 120.2 . . ?
 C15 C18 H18A 109.5 . . ?
 C15 C18 H18B 109.5 . . ?
 C15 C18 H18C 109.5 . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 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
 N1 S1 C12 C13 78.4(4) . . . . ?
 N1 S1 C12 C17 -98.1(3) . . . . ?
 O1 C1 C2 C3 -144.1(4) . . . . ?
 O1 C1 C2 C7 39.6(5) . . . . ?
 O2 C1 C2 C3 37.4(6) . . . . ?
 O2 C1 C2 C7 -139.0(4) . . . . ?
 O3 C6 C7 C2 -179.7(4) . . . . ?
 O4 S1 C12 C13 -36.7(4) . . . . ?
 O4 S1 C12 C17 146.8(3) . . . . ?
 O5 S1 C12 C13 -166.4(3) . . . . ?
 O5 S1 C12 C17 17.1(4) . . . . ?
 S1 N1 C9 C8 -137.8(3) . . . . ?
 S1 N1 C9 C10 98.0(4) . . . . ?
 S1 C12 C13 C14 -178.2(4) . . . . ?
 S1 C12 C17 C16 177.0(4) . . . . ?
 C1 C2 C3 C4 -176.3(4) . . . . ?
 C1 C2 C3 C8 5.2(6) . . . . ?
 C1 C2 C7 C6 176.1(4) . . . . ?
 C2 C3 C4 C5 0.5(6) . . . . ?
 C2 C3 C8 C9 -105.6(5) . . . . ?
 C3 C2 C7 C6 -0.2(6) . . . . ?
 C3 C4 C5 C6 -0.7(7) . . . . ?
 C3 C8 C9 N1 62.0(4) . . . . ?
 C3 C8 C9 C10 -174.6(4) . . . . ?
 C4 C3 C8 C9 75.8(5) . . . . ?
 C4 C5 C6 O3 -179.9(4) . . . . ?
 C4 C5 C6 C7 0.4(6) . . . . ?
 C5 C6 C7 C2 0.0(6) . . . . ?
 C7 C2 C3 C4 -0.1(6) . . . . ?
 C7 C2 C3 C8 -178.6(4) . . . . ?
 C8 C3 C4 C5 179.2(4) . . . . ?
 C9 N1 S1 O4 177.5(3) . . . . ?
 C9 N1 S1 O5 -53.7(3) . . . . ?
 C9 N1 S1 C12 60.8(3) . . . . ?
 C11 O3 C6 C5 -8.7(7) . . . . ?
 C11 O3 C6 C7 171.0(4) . . . . ?
 C12 C13 C14 C15 1.5(7) . . . . ?
 C13 C12 C17 C16 0.5(6) . . . . ?
 C13 C14 C15 C16 -0.2(7) . . . . ?
 C13 C14 C15 C18 178.6(5) . . . . ?
 C14 C15 C16 C17 -1.1(7) . . . . ?
 C15 C16 C17 C12 0.9(7) . . . . ?
 C17 C12 C13 C14 -1.7(6) . . . . ?
 C18 C15 C16 C17 -179.9(4) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.94(12)
 2 0.06(12)

