 
data_k1626 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_sum 
 'C17 H25 N3 O6 S' 
_chemical_formula_weight          399.46 
 
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' 
 'N'  'N'   0.0311   0.0180 
 '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' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    'P 21 21 21' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    7.4329(2) 
_cell_length_b                    14.0813(4) 
_cell_length_c                    18.3821(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1923.96(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     8179 
_cell_measurement_theta_min       3.95 
_cell_measurement_theta_max       66.65 
 
_exptl_crystal_description        column 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.15 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_diffrn     1.379 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              848 
_exptl_absorpt_coefficient_mu     1.842 
_exptl_absorpt_correction_type    Empirical 
_exptl_absorpt_correction_T_min   0.5298 
_exptl_absorpt_correction_T_max   0.7528 
_exptl_absorpt_process_details    'SAINT v7.60A' 
 
_publ_section_experimental 
; 
  All measurements were made with a Bruker DUO platform 
 diffractometer equipped with a 4K CCD APEX II detector and an
 Incoatec 30 Watt Cu microsource with compact multilayer optics.
 A hemisphere of data (2713 frames at 4 cm detector distance)
 was collected using a narrow-frame algorithm with scan widths
 of 0.50° in omega and an exposure time of 25 s/frame.  The
 data were integrated using the Bruker-Nonius SAINT program, 
 with the intensities corrected for Lorentz factor, polarization, 
 air absorption, and absorption due to variation in the path 
 length through the detector faceplate.  The data were scaled,
 and an absorption correction was applied using SADABS.  Redundant 
 reflections were averaged.  Final cell constants were refined 
 using 8179 reflections having I>10σ(I), and these, along with 
 other information pertinent to data collection and refinement, 
 are listed in Table 1.  The Laue symmetry was determined to 
 be mmm, and from the systematic absences noted the space group 
 was shown unambiguously to be P2(1)2(1)2(1).
; 
 
_publ_section_figure_captions 
;
 Fig. 1 -- View of the molecule showing the atom numbering
   scheme.  Thermal ellipsoids are 50% equiprobability envelopes,
   with hydrogens as spheres of arbitrary diameter.

 Fig. 2 -- Isotropic view of the molecule.

 Fig. 3 -- Intermolecular hydrogen bonding.

 Fig. 4 -- Packing of the molecules in the unit cell.
;
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'Incoatec 30 Watt Cu microsource' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker DUO APEX II CCD'
_diffrn_measurement_method        CCD 
_diffrn_detector_area_resol_mean  4K 
_diffrn_standards_decay_%         0.0 
_diffrn_reflns_number             12918
_diffrn_reflns_av_R_equivalents   0.0264
_diffrn_reflns_av_sigmaI/netI     0.0266 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          3.95 
_diffrn_reflns_theta_max          66.65 
_reflns_number_total              3250 
_reflns_number_gt                 3167 
_reflns_threshold_expression      >3.99sigma(I) 
 
_computing_data_collection        'APEX2 v2013.4-1 (Bruker-Nonius, 2013)' 
_computing_cell_refinement        'SAINT v7.60A (Bruker-Nonius, 2013)' 
_computing_data_reduction         'SAINT v7.60A (Bruker-Nonius, 2013)' 
_computing_structure_solution     'SHELXS v6.12 (G.M. Sheldrick, 2001)' 
_computing_structure_refinement   'SHELXL v6.12 (G.M. Sheldrick, 2001)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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 > 4sigma(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. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0273P)²+0.3729P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0035(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.053(11)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          3232 
_refine_ls_number_parameters      251 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0211 
_refine_ls_R_factor_gt            0.0207 
_refine_ls_wR_factor_ref          0.0552 
_refine_ls_wR_factor_gt           0.0545 
_refine_ls_goodness_of_fit_ref    1.051 
_refine_ls_restrained_S_all       1.051 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
S1 S 0.82016(4) 0.30225(2) 0.171028(16) 0.01772(9) Uani 1 1 d . . . 
O1 O 0.71915(15) 0.23277(6) 0.21090(5) 0.0248(2) Uani 1 1 d . . . 
O2 O 0.99070(14) 0.27450(7) 0.14125(5) 0.0234(2) Uani 1 1 d . . . 
O3 O 0.99141(14) 0.45798(7) 0.07434(5) 0.0256(2) Uani 1 1 d . . . 
O4 O 0.97797(15) 0.40520(8) -0.03649(5) 0.0306(3) Uani 1 1 d . . . 
O5 O 0.51028(14) 0.36438(7) 0.44005(5) 0.0231(2) Uani 1 1 d . . . 
O6 O 0.37292(14) 0.43447(7) 0.34517(5) 0.0259(2) Uani 1 1 d . . . 
N1 N 0.84862(16) 0.39740(7) 0.21849(6) 0.0170(2) Uani 1 1 d . . . 
N2 N 0.88305(16) 0.56282(8) 0.29823(6) 0.0210(3) Uani 1 1 d . . . 
H2N H 0.891(2) 0.6244(14) 0.3102(9) 0.027 Uiso 1 1 d . . . 
N3 N 0.91278(16) 0.41822(8) 0.02439(6) 0.0207(3) Uani 1 1 d . . . 
C1 C 0.69290(19) 0.43352(9) 0.26049(7) 0.0168(3) Uani 1 1 d . . . 
H1 H 0.5801 0.4171 0.2336 0.020 Uiso 1 1 calc R . . 
C2 C 0.70950(19) 0.54236(9) 0.26390(7) 0.0179(3) Uani 1 1 d . . . 
H2 H 0.6131 0.5662 0.2972 0.022 Uiso 1 1 calc R . . 
C3 C 1.03658(19) 0.53178(10) 0.25399(8) 0.0222(3) Uani 1 1 d . . . 
H3A H 1.1505 0.5500 0.2781 0.027 Uiso 1 1 calc R . . 
H3B H 1.0324 0.5630 0.2058 0.027 Uiso 1 1 calc R . . 
C4 C 1.02898(19) 0.42477(10) 0.24473(7) 0.0203(3) Uani 1 1 d . . . 
H4A H 1.1215 0.4041 0.2093 0.024 Uiso 1 1 calc R . . 
H4B H 1.0539 0.3933 0.2918 0.024 Uiso 1 1 calc R . . 
C5 C 0.6739(2) 0.33749(9) 0.09862(7) 0.0183(3) Uani 1 1 d . . . 
C6 C 0.72682(19) 0.38620(9) 0.03589(7) 0.0191(3) Uani 1 1 d . . . 
C7 C 0.6068(2) 0.40680(10) -0.01945(8) 0.0232(3) Uani 1 1 d . . . 
H7 H 0.6468 0.4384 -0.0622 0.028 Uiso 1 1 calc R . . 
C8 C 0.4276(2) 0.38101(11) -0.01204(8) 0.0266(3) Uani 1 1 d . . . 
H8 H 0.3433 0.3966 -0.0490 0.032 Uiso 1 1 calc R . . 
C9 C 0.3722(2) 0.33247(10) 0.04937(8) 0.0256(3) Uani 1 1 d . . . 
H9 H 0.2495 0.3148 0.0545 0.031 Uiso 1 1 calc R . . 
C10 C 0.4946(2) 0.30943(10) 0.10356(7) 0.0217(3) Uani 1 1 d . . . 
H10 H 0.4556 0.2740 0.1446 0.026 Uiso 1 1 calc R . . 
C11 C 0.68470(19) 0.38807(9) 0.33609(7) 0.0191(3) Uani 1 1 d . . . 
H11A H 0.7114 0.3194 0.3317 0.023 Uiso 1 1 calc R . . 
H11B H 0.7787 0.4169 0.3672 0.023 Uiso 1 1 calc R . . 
C12 C 0.5045(2) 0.40027(9) 0.37223(7) 0.0181(3) Uani 1 1 d . . . 
C13 C 0.3424(2) 0.36347(10) 0.48038(7) 0.0234(3) Uani 1 1 d . . . 
H13A H 0.2443 0.3366 0.4503 0.028 Uiso 1 1 calc R . . 
H13B H 0.3086 0.4287 0.4952 0.028 Uiso 1 1 calc R . . 
C14 C 0.3754(3) 0.30258(14) 0.54584(9) 0.0419(4) Uani 1 1 d . . . 
H14A H 0.2659 0.2997 0.5754 0.063 Uiso 1 1 calc R . . 
H14B H 0.4735 0.3298 0.5747 0.063 Uiso 1 1 calc R . . 
H14C H 0.4086 0.2384 0.5302 0.063 Uiso 1 1 calc R . . 
C15 C 0.6792(2) 0.58869(9) 0.18839(7) 0.0210(3) Uani 1 1 d . . . 
H15 H 0.7623 0.5579 0.1527 0.025 Uiso 1 1 calc R . . 
C16 C 0.4867(2) 0.57542(11) 0.16158(8) 0.0299(3) Uani 1 1 d . . . 
H16A H 0.4748 0.6025 0.1127 0.045 Uiso 1 1 calc R . . 
H16B H 0.4036 0.6077 0.1948 0.045 Uiso 1 1 calc R . . 
H16C H 0.4579 0.5075 0.1600 0.045 Uiso 1 1 calc R . . 
C17 C 0.7227(2) 0.69473(10) 0.19109(8) 0.0308(3) Uani 1 1 d . . . 
H17A H 0.7031 0.7228 0.1430 0.046 Uiso 1 1 calc R . . 
H17B H 0.8487 0.7035 0.2054 0.046 Uiso 1 1 calc R . . 
H17C H 0.6443 0.7259 0.2267 0.046 Uiso 1 1 calc R . . 
 
 
_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 1.4346(10) . ? 
S1 O2 1.4350(11) . ? 
S1 N1 1.6127(11) . ? 
S1 C5 1.7887(14) . ? 
O3 N3 1.2240(15) . ? 
O4 N3 1.2331(16) . ? 
O5 C12 1.3459(16) . ? 
O5 C13 1.4514(17) . ? 
O6 C12 1.1982(17) . ? 
N1 C4 1.4760(18) . ? 
N1 C1 1.4814(17) . ? 
N2 C2 1.4647(18) . ? 
N2 C3 1.4679(18) . ? 
N3 C6 1.4692(19) . ? 
C1 C11 1.5310(17) . ? 
C1 C2 1.5390(18) . ? 
C2 C15 1.5501(17) . ? 
C3 C4 1.5175(19) . ? 
C5 C10 1.393(2) . ? 
C5 C6 1.3982(19) . ? 
C6 C7 1.384(2) . ? 
C7 C8 1.387(2) . ? 
C8 C9 1.382(2) . ? 
C9 C10 1.388(2) . ? 
C11 C12 1.505(2) . ? 
C13 C14 1.498(2) . ? 
C15 C16 1.525(2) . ? 
C15 C17 1.5287(19) . ? 
 
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 O2 118.13(6) . . ? 
O1 S1 N1 111.03(6) . . ? 
O2 S1 N1 108.46(6) . . ? 
O1 S1 C5 104.56(6) . . ? 
O2 S1 C5 109.18(6) . . ? 
N1 S1 C5 104.58(6) . . ? 
C12 O5 C13 116.68(11) . . ? 
C4 N1 C1 116.72(10) . . ? 
C4 N1 S1 120.86(9) . . ? 
C1 N1 S1 117.69(9) . . ? 
C2 N2 C3 112.79(10) . . ? 
O3 N3 O4 124.13(12) . . ? 
O3 N3 C6 118.79(11) . . ? 
O4 N3 C6 117.04(12) . . ? 
N1 C1 C11 111.14(10) . . ? 
N1 C1 C2 107.49(11) . . ? 
C11 C1 C2 112.49(10) . . ? 
N2 C2 C1 106.50(11) . . ? 
N2 C2 C15 115.54(11) . . ? 
C1 C2 C15 111.78(11) . . ? 
N2 C3 C4 109.20(11) . . ? 
N1 C4 C3 109.25(11) . . ? 
C10 C5 C6 117.52(13) . . ? 
C10 C5 S1 117.01(10) . . ? 
C6 C5 S1 125.37(11) . . ? 
C7 C6 C5 121.86(13) . . ? 
C7 C6 N3 115.87(12) . . ? 
C5 C6 N3 122.27(12) . . ? 
C6 C7 C8 119.46(14) . . ? 
C9 C8 C7 119.72(15) . . ? 
C8 C9 C10 120.41(14) . . ? 
C9 C10 C5 120.96(13) . . ? 
C12 C11 C1 112.86(11) . . ? 
O6 C12 O5 124.16(13) . . ? 
O6 C12 C11 126.09(12) . . ? 
O5 C12 C11 109.73(12) . . ? 
O5 C13 C14 105.93(12) . . ? 
C16 C15 C17 109.19(12) . . ? 
C16 C15 C2 111.97(12) . . ? 
C17 C15 C2 110.57(11) . . ? 
 
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 
O1 S1 N1 C4 112.17(10) . . . . ? 
O2 S1 N1 C4 -19.20(12) . . . . ? 
C5 S1 N1 C4 -135.61(10) . . . . ? 
O1 S1 N1 C1 -42.66(11) . . . . ? 
O2 S1 N1 C1 -174.03(9) . . . . ? 
C5 S1 N1 C1 69.56(10) . . . . ? 
C4 N1 C1 C11 -67.89(14) . . . . ? 
S1 N1 C1 C11 87.98(12) . . . . ? 
C4 N1 C1 C2 55.60(13) . . . . ? 
S1 N1 C1 C2 -148.53(9) . . . . ? 
C3 N2 C2 C1 65.48(13) . . . . ? 
C3 N2 C2 C15 -59.30(14) . . . . ? 
N1 C1 C2 N2 -58.24(12) . . . . ? 
C11 C1 C2 N2 64.42(14) . . . . ? 
N1 C1 C2 C15 68.81(14) . . . . ? 
C11 C1 C2 C15 -168.53(11) . . . . ? 
C2 N2 C3 C4 -62.37(14) . . . . ? 
C1 N1 C4 C3 -52.05(14) . . . . ? 
S1 N1 C4 C3 152.89(9) . . . . ? 
N2 C3 C4 N1 51.44(14) . . . . ? 
O1 S1 C5 C10 12.58(12) . . . . ? 
O2 S1 C5 C10 139.89(10) . . . . ? 
N1 S1 C5 C10 -104.21(10) . . . . ? 
O1 S1 C5 C6 -163.73(11) . . . . ? 
O2 S1 C5 C6 -36.42(12) . . . . ? 
N1 S1 C5 C6 79.49(12) . . . . ? 
C10 C5 C6 C7 0.42(19) . . . . ? 
S1 C5 C6 C7 176.71(10) . . . . ? 
C10 C5 C6 N3 -179.27(12) . . . . ? 
S1 C5 C6 N3 -2.97(18) . . . . ? 
O3 N3 C6 C7 134.55(13) . . . . ? 
O4 N3 C6 C7 -43.52(17) . . . . ? 
O3 N3 C6 C5 -45.75(18) . . . . ? 
O4 N3 C6 C5 136.18(13) . . . . ? 
C5 C6 C7 C8 1.8(2) . . . . ? 
N3 C6 C7 C8 -178.46(12) . . . . ? 
C6 C7 C8 C9 -2.0(2) . . . . ? 
C7 C8 C9 C10 0.0(2) . . . . ? 
C8 C9 C10 C5 2.3(2) . . . . ? 
C6 C5 C10 C9 -2.50(19) . . . . ? 
S1 C5 C10 C9 -179.10(10) . . . . ? 
N1 C1 C11 C12 -163.61(10) . . . . ? 
C2 C1 C11 C12 75.80(14) . . . . ? 
C13 O5 C12 O6 3.30(19) . . . . ? 
C13 O5 C12 C11 -175.10(11) . . . . ? 
C1 C11 C12 O6 5.69(19) . . . . ? 
C1 C11 C12 O5 -175.95(10) . . . . ? 
C12 O5 C13 C14 168.21(13) . . . . ? 
N2 C2 C15 C16 -171.94(11) . . . . ? 
C1 C2 C15 C16 66.07(15) . . . . ? 
N2 C2 C15 C17 -49.92(16) . . . . ? 
C1 C2 C15 C17 -171.92(12) . . . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N2 H2N O2  0.897(19) 2.457(19) 3.3171(15) 160.9(15) 3_755 
 
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              66.65 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.194 
_refine_diff_density_min   -0.202 
_refine_diff_density_rms    0.035 

