####################################################################### 
# 
# 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_reu-073
_audit_creation_date               2018-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number       2018/3
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_phone        ?
_audit_update_record
;
2018-05-27 deposited with the CCDC.
2018-10-28 downloaded from the CCDC.
;
_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. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C2 H6 O S, C15 H13 N3 O4'
_chemical_formula_sum              'C17 H19 N3 O5 S'
_chemical_formula_weight           377.41
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C15 H13 N3 O4'
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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     13.2944(6)
_cell_length_b                     9.4754(4)
_cell_length_c                     13.8198(6)
_cell_angle_alpha                  90
_cell_angle_beta                   90.284(4)
_cell_angle_gamma                  90
_cell_volume                       1740.86(13)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      10586
_cell_measurement_temperature      100(10)
_cell_measurement_theta_max        30.7850
_cell_measurement_theta_min        3.0270
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.221
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.95049
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light white'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      white
_exptl_crystal_density_diffrn      1.440
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               792
_exptl_crystal_size_max            0.7
_exptl_crystal_size_mid            0.5
_exptl_crystal_size_min            0.4
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0332
_diffrn_reflns_av_unetI/netI       0.0225
_diffrn_reflns_Laue_measured_fraction_full  0.994
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              21902
_diffrn_reflns_point_group_measured_fraction_full  0.994
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.499
_diffrn_reflns_theta_min           2.640
_diffrn_ambient_temperature        100(10)
_diffrn_detector_area_resol_mean   8.1048
_diffrn_measured_fraction_theta_full  0.994
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -66.00  -35.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00   -5.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00  -19.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -57.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   11.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741  -99.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   25.00   65.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741  -99.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00  -10.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741  -57.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega  -97.00  -72.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   -6.00   22.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741   86.0000  -62.0000 28

#__ type_ start__ end____ width___ exp.time_
  9 omega   64.00   90.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   56.00   81.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741 -178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  -60.00  -34.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  -95.00  -67.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  100.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741 -178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   35.00   61.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741 -178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   64.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  -10.00   97.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -       23.6741   19.0000 -120.0000 107

#__ type_ start__ end____ width___ exp.time_
 17 omega  -88.00  -38.00   1.0000    1.3200
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -57.0000   90.0000 50
;
_diffrn_measurement_device_type    'Xcalibur, Eos'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        0.0453796000
_diffrn_orient_matrix_UB_12        0.0183336000
_diffrn_orient_matrix_UB_13        0.0241394000
_diffrn_orient_matrix_UB_21        -0.0280524000
_diffrn_orient_matrix_UB_22        0.0279969000
_diffrn_orient_matrix_UB_23        0.0390513000
_diffrn_orient_matrix_UB_31        0.0006155000
_diffrn_orient_matrix_UB_32        -0.0669799000
_diffrn_orient_matrix_UB_33        0.0229177000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3668
_reflns_number_total               3978
_reflns_odcompleteness_completeness  99.79
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.803
_refine_diff_density_min           -0.715
_refine_diff_density_rms           0.053
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       237
_refine_ls_number_reflns           3978
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0412
_refine_ls_R_factor_gt             0.0373
_refine_ls_restrained_S_all        1.056
_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)+(0.0421P)²+1.2587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0909
_refine_ls_wR_factor_ref           0.0935
_refine_special_details            ?
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.014) H2(0.017) H14(0.016) H5(0.018) H8A(0.016) H8B(0.016)
 H11(0.019) H9A(0.017) H9B(0.017) H12(0.02) H4(0.024) H2A(0.024) H3(0.027)
 H16A(0.036) H16B(0.036) H16C(0.036) H17A(0.031) H17B(0.031) H17C(0.031)
 Fixed X: H1(0.925629) H2(0.740014) H14(0.583548) H5(0.931337) H8A(0.863779)
 H8B(0.961979) H11(0.648916) H9A(0.876196) H9B(0.806008) H12(0.535774)
 H4(0.890131) H2A(0.69875) H3(0.776066) H16A(0.787358) H16B(0.823571)
 H16C(0.763224) H17A(1.053927) H17B(1.001129) H17C(0.949767)
 Fixed Y: H1(0.504071) H2(0.582145) H14(0.456211) H5(0.398105) H8A(0.245701)
 H8B(0.318894) H11(0.257508) H9A(0.47648) H9B(0.344293) H12(0.150228)
 H4(0.554168) H2A(0.754188) H3(0.734153) H16A(0.960752) H16B(1.026122)
 H16C(0.883984) H17A(0.916902) H17B(1.047949) H17C(0.968882)
 Fixed Z: H1(0.447918) H2(0.310929) H14(0.601737) H5(0.713442) H8A(0.376652)
 H8B(0.338643) H11(0.30053) H9A(0.248898) H9B(0.238883) H12(0.403935)
 H4(0.835809) H2A(0.656306) H3(0.806871) H16A(0.376663) H16B(0.475047)
 H16C(0.474315) H17A(0.331277) H17B(0.378089) H17C(0.291312)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_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 0.92717(3) 0.84354(4) 0.43181(2) 0.01510(10) Uani 1 1 d . . . . .
 O2 O 0.84963(8) 0.24665(11) 0.55204(7) 0.0150(2) Uani 1 1 d . . . . .
 O1 O 0.71741(8) 0.59991(10) 0.50700(7) 0.0139(2) Uani 1 1 d . . . . .
 O0AA O 0.90388(9) 0.70974(11) 0.37613(8) 0.0185(2) Uani 1 1 d . . . . .
 O4 O 0.45455(9) 0.29316(13) 0.65089(8) 0.0244(3) Uani 1 1 d . . . . .
 O3 O 0.43308(9) 0.12164(12) 0.54915(9) 0.0267(3) Uani 1 1 d . . . . .
 N1 N 0.89954(9) 0.42109(12) 0.45020(8) 0.0114(2) Uani 1 1 d . . . . .
 H1 H 0.925629 0.504071 0.447918 0.014 Uiso 1 1 calc R . . . .
 N2 N 0.74848(9) 0.49450(13) 0.32493(8) 0.0138(2) Uani 1 1 d . . . . .
 H2 H 0.740014 0.582145 0.310929 0.017 Uiso 1 1 calc R . . . .
 N3 N 0.47361(9) 0.23250(14) 0.57453(10) 0.0186(3) Uani 1 1 d . . . . .
 C15 C 0.66467(10) 0.47896(14) 0.47945(10) 0.0123(3) Uani 1 1 d . . . . .
 C7 C 0.86412(10) 0.37208(14) 0.53462(10) 0.0112(3) Uani 1 1 d . . . . .
 C10 C 0.68346(10) 0.42444(15) 0.38671(10) 0.0129(3) Uani 1 1 d . . . . .
 C14 C 0.59666(10) 0.41728(15) 0.54133(10) 0.0137(3) Uani 1 1 d . . . . .
 H14 H 0.583548 0.456211 0.601737 0.016 Uiso 1 1 calc R . . . .
 C5 C 0.88489(11) 0.46952(16) 0.70160(10) 0.0153(3) Uani 1 1 d . . . . .
 H5 H 0.931337 0.398105 0.713442 0.018 Uiso 1 1 calc R . . . .
 C8 C 0.89454(11) 0.33611(15) 0.36238(10) 0.0131(3) Uani 1 1 d . . . . .
 H8A H 0.863779 0.245701 0.376652 0.016 Uiso 1 1 calc R . . . .
 H8B H 0.961979 0.318894 0.338643 0.016 Uiso 1 1 calc R . . . .
 C1 C 0.76893(11) 0.58713(15) 0.59515(10) 0.0136(3) Uani 1 1 d . . . . .
 C6 C 0.84065(10) 0.48137(14) 0.61030(10) 0.0126(3) Uani 1 1 d . . . . .
 C11 C 0.63524(11) 0.29822(16) 0.36027(10) 0.0158(3) Uani 1 1 d . . . . .
 H11 H 0.648916 0.257508 0.300530 0.019 Uiso 1 1 calc R . . . .
 C9 C 0.83245(11) 0.41312(15) 0.28431(10) 0.0141(3) Uani 1 1 d . . . . .
 H9A H 0.876196 0.476480 0.248898 0.017 Uiso 1 1 calc R . . . .
 H9B H 0.806008 0.344293 0.238883 0.017 Uiso 1 1 calc R . . . .
 C13 C 0.54836(10) 0.29534(16) 0.51075(10) 0.0149(3) Uani 1 1 d . . . . .
 C12 C 0.56768(11) 0.23364(16) 0.42187(11) 0.0170(3) Uani 1 1 d . . . . .
 H12 H 0.535774 0.150228 0.403935 0.020 Uiso 1 1 calc R . . . .
 C4 C 0.86034(12) 0.56325(17) 0.77510(11) 0.0196(3) Uani 1 1 d . . . . .
 H4 H 0.890131 0.554168 0.835809 0.024 Uiso 1 1 calc R . . . .
 C2 C 0.74518(12) 0.68264(17) 0.66783(11) 0.0200(3) Uani 1 1 d . . . . .
 H2A H 0.698750 0.754188 0.656306 0.024 Uiso 1 1 calc R . . . .
 C3 C 0.79141(12) 0.67037(18) 0.75797(11) 0.0225(3) Uani 1 1 d . . . . .
 H3 H 0.776066 0.734153 0.806871 0.027 Uiso 1 1 calc R . . . .
 C16 C 0.81201(12) 0.93972(17) 0.44046(13) 0.0239(3) Uani 1 1 d . . . . .
 H16A H 0.787358 0.960752 0.376663 0.036 Uiso 1 1 calc GR . . . .
 H16B H 0.823571 1.026122 0.475047 0.036 Uiso 1 1 calc GR . . . .
 H16C H 0.763224 0.883984 0.474315 0.036 Uiso 1 1 calc GR . . . .
 C17 C 0.99032(13) 0.95755(16) 0.34845(11) 0.0209(3) Uani 1 1 d . . . . .
 H17A H 1.053927 0.916902 0.331277 0.031 Uiso 1 1 calc GR . . . .
 H17B H 1.001129 1.047949 0.378089 0.031 Uiso 1 1 calc GR . . . .
 H17C H 0.949767 0.968882 0.291312 0.031 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 O0AA 1.5143(10) . ?
 S1 C16 1.7861(16) . ?
 S1 C17 1.7912(16) . ?
 O2 C7 1.2280(17) . ?
 O1 C15 1.3955(17) . ?
 O1 C1 1.3999(17) . ?
 O4 N3 1.2292(18) . ?
 O3 N3 1.2308(18) . ?
 N1 C7 1.3431(17) . ?
 N1 C8 1.4578(17) . ?
 N2 C10 1.3871(18) . ?
 N2 C9 1.4704(18) . ?
 N3 C13 1.4586(18) . ?
 C15 C10 1.4055(19) . ?
 C15 C14 1.378(2) . ?
 C7 C6 1.5055(18) . ?
 C10 C11 1.404(2) . ?
 C14 C13 1.387(2) . ?
 C5 C6 1.394(2) . ?
 C5 C4 1.389(2) . ?
 C8 C9 1.5392(19) . ?
 C1 C6 1.398(2) . ?
 C1 C2 1.389(2) . ?
 C11 C12 1.383(2) . ?
 C13 C12 1.385(2) . ?
 C4 C3 1.387(2) . ?
 C2 C3 1.391(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
 O0AA S1 C16 106.74(7) . . ?
 O0AA S1 C17 105.87(7) . . ?
 C16 S1 C17 98.05(8) . . ?
 C15 O1 C1 114.16(10) . . ?
 C7 N1 C8 121.16(11) . . ?
 C10 N2 C9 117.43(11) . . ?
 O4 N3 O3 123.50(13) . . ?
 O4 N3 C13 118.16(13) . . ?
 O3 N3 C13 118.35(13) . . ?
 O1 C15 C10 117.34(12) . . ?
 C14 C15 O1 120.63(12) . . ?
 C14 C15 C10 122.03(13) . . ?
 O2 C7 N1 124.12(13) . . ?
 O2 C7 C6 119.76(12) . . ?
 N1 C7 C6 116.12(12) . . ?
 N2 C10 C15 119.97(13) . . ?
 N2 C10 C11 122.17(13) . . ?
 C11 C10 C15 117.86(13) . . ?
 C15 C14 C13 117.95(13) . . ?
 C4 C5 C6 120.70(14) . . ?
 N1 C8 C9 110.11(11) . . ?
 C6 C1 O1 121.50(12) . . ?
 C2 C1 O1 117.44(13) . . ?
 C2 C1 C6 121.05(13) . . ?
 C5 C6 C7 119.03(12) . . ?
 C5 C6 C1 118.53(13) . . ?
 C1 C6 C7 122.18(12) . . ?
 C12 C11 C10 120.90(13) . . ?
 N2 C9 C8 112.74(11) . . ?
 C14 C13 N3 118.15(13) . . ?
 C12 C13 N3 119.56(13) . . ?
 C12 C13 C14 122.28(13) . . ?
 C11 C12 C13 118.86(14) . . ?
 C3 C4 C5 120.03(14) . . ?
 C1 C2 C3 119.46(14) . . ?
 C4 C3 C2 120.17(14) . . ?

_database_code_depnum_ccdc_archive  'CCDC 1845563'
_olex2_submission_special_instructions  'No special instructions were received'
