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In the title compound, C15H23N3O9S, the hexopyranosyl ring adopts a chair conformation. The acetyl group at C4 occupies an axial position, while all other substituents are equatorial. The mol­ecules are linked by C—H...O hydrogen bonds into ribbons parallel to the a axis, and N—H...O inter­actions provide further stability in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040365/sj6177sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040365/sj6177Isup2.hkl
Contains datablock I

CCDC reference: 296664

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.047
  • wR factor = 0.127
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT416_ALERT_2_B Short Intra D-H..H-D H1A .. H3A .. 1.71 Ang.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.09 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.84 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C14 PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3B ... ? PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.80 Deg. O5B -C9 -O5A 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.04 From the CIF: _reflns_number_total 4041 Count of symmetry unique reflns 2352 Completeness (_total/calc) 171.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1689 Fraction of Friedel pairs measured 0.718 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Substituted thioureas and thiosemicarbazides have attracted much attention in recent years because of their anti-HIV potential (Venkatachalam et al., 2001) and their importance in the preparation of corresponding semicarbazides (Li et al., 2001) and heterocyclic compounds (Wang et al., 2001). We have reported the synthesis and structure of N-amino-N-(2,3,4,6-tetra-O-acetyl-β-D– xylopyranosyl)thiocarbamide (II) (Yang et al., 2004) and this work has been extended to the synthesis of the title compound (I) whose structure is reported here (Fig. 1, Table 1). All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and compare well with those values in compound (II). The acetyl group at C4 occupies an axial position, while all other substituents are equatorial. The pyranosyl ring adopts a chair conformation with the S1 atom in a synperiplanar position with respect to C1. The C1—N1—C15—S1 torsion angle is −5.5 (4)°. Atom O5 is disordered over two positions, with refined site occupancies of 0.32 (6) for O5A and 0.68 (6) for O5B.

In the crystal of (I), molecules are linked into ribbons along the a axis by C12—H12C···O5B hydrogen bonds (Fig. 2). The packing is further stabilized by N2—H2A···O1 interactions (Table 2), forming a three-dimensional framework.

Experimental top

The title compound was prepared by the method of Yang et al. (2004).

Refinement top

All H atoms were fixed geometrically and treated as riding, with C—H distances = 0.96–0.98 Å and N—H distances = 0.86 Å. Uiso(H)=1.2Ueq(C) [For the methyl H atoms Uiso(H)=1.5Ueq(C)] and Uiso(H)=1.2Ueq(N).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of the compound (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hn atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram for (I), showing the formation of ribbons along the a axis. H bonds are drawn as dashed lines.
4-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazide top
Crystal data top
C15H23N3O9SF(000) = 888
Mr = 421.42Dx = 1.369 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3602 reflections
a = 7.5445 (11) Åθ = 2.4–22.3°
b = 8.6792 (13) ŵ = 0.21 mm1
c = 31.229 (5) ÅT = 293 K
V = 2044.9 (5) Å3Needle, colourless
Z = 40.30 × 0.14 × 0.11 mm
Data collection top
Simens SMART CCD area-detector
diffractometer
4041 independent reflections
Radiation source: fine-focus sealed tube3407 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 710
Tmin = 0.940, Tmax = 0.977l = 3738
11659 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0739P)2 + 0.2979P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4041 reflectionsΔρmax = 0.22 e Å3
263 parametersΔρmin = 0.25 e Å3
0 restraintsAbsolute structure: Flack (1983), 1690 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (12)
Crystal data top
C15H23N3O9SV = 2044.9 (5) Å3
Mr = 421.42Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.5445 (11) ŵ = 0.21 mm1
b = 8.6792 (13) ÅT = 293 K
c = 31.229 (5) Å0.30 × 0.14 × 0.11 mm
Data collection top
Simens SMART CCD area-detector
diffractometer
4041 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3407 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.977Rint = 0.024
11659 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.22 e Å3
S = 1.02Δρmin = 0.25 e Å3
4041 reflectionsAbsolute structure: Flack (1983), 1690 Friedel pairs
263 parametersAbsolute structure parameter: 0.03 (12)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.31442 (12)0.74323 (11)0.22479 (3)0.0739 (3)
O10.2707 (2)0.37388 (19)0.17692 (5)0.0434 (4)
O20.1450 (3)0.1768 (3)0.17125 (7)0.0624 (6)
O30.1156 (4)0.0515 (3)0.20197 (12)0.1051 (10)
O40.2116 (2)0.14298 (18)0.11188 (6)0.0455 (4)
O5A0.0234 (19)0.0254 (18)0.0862 (18)0.078 (7)0.32 (6)
O5B0.023 (3)0.0456 (16)0.0633 (10)0.100 (7)0.68 (6)
O60.2609 (2)0.3429 (2)0.04584 (5)0.0470 (4)
O70.0654 (4)0.4995 (4)0.01537 (8)0.1018 (10)
O80.4767 (2)0.56774 (19)0.08519 (6)0.0444 (4)
O90.7509 (3)0.4849 (3)0.10133 (7)0.0616 (5)
N10.5056 (3)0.5449 (3)0.17836 (7)0.0477 (5)
H1A0.60660.50610.17150.057*
N20.6524 (3)0.6699 (3)0.23097 (7)0.0568 (6)
H2A0.65500.72710.25340.068*
N30.8091 (4)0.6027 (3)0.21635 (8)0.0613 (7)
H3A0.80790.54530.19390.074*
H3B0.90690.61880.22980.074*
C10.3539 (3)0.4987 (3)0.15507 (8)0.0409 (6)
H1B0.27090.58540.15350.049*
C20.3979 (3)0.4443 (3)0.10951 (8)0.0372 (5)
H2B0.47660.35450.11020.045*
C30.2238 (3)0.4047 (3)0.08758 (7)0.0390 (6)
H3C0.15310.49880.08450.047*
C40.1188 (3)0.2877 (3)0.11283 (8)0.0379 (5)
H4A0.00100.27530.10010.045*
C50.1008 (3)0.3405 (3)0.15916 (8)0.0419 (6)
H5A0.02660.43310.16030.050*
C60.0242 (4)0.2193 (4)0.18814 (9)0.0541 (7)
H6A0.10170.13020.18910.065*
H6B0.01120.25950.21700.065*
C70.1999 (5)0.0364 (4)0.17996 (12)0.0731 (9)
C80.3802 (6)0.0061 (6)0.16217 (16)0.1152 (18)
H8A0.41490.09760.16880.173*
H8B0.37820.01950.13170.173*
H8C0.46340.07680.17460.173*
C90.1405 (5)0.0281 (4)0.08892 (13)0.0723 (10)
C100.2534 (6)0.1120 (4)0.09034 (17)0.1056 (17)
H10A0.19990.19180.07340.158*
H10B0.26460.14640.11940.158*
H10C0.36870.08840.07910.158*
C110.1620 (4)0.3929 (4)0.01282 (9)0.0533 (7)
C120.1868 (5)0.2940 (5)0.02565 (9)0.0753 (10)
H12A0.11590.33310.04880.113*
H12B0.15110.19050.01910.113*
H12C0.30940.29480.03390.113*
C130.6576 (4)0.5724 (3)0.08259 (9)0.0482 (6)
C140.7158 (5)0.6992 (4)0.05388 (13)0.0801 (11)
H14A0.84290.70040.05230.120*
H14B0.67440.79590.06500.120*
H14C0.66760.68330.02580.120*
C150.4988 (4)0.6473 (3)0.21088 (8)0.0497 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0666 (5)0.0749 (6)0.0802 (6)0.0066 (5)0.0207 (4)0.0332 (5)
O10.0424 (9)0.0477 (10)0.0400 (9)0.0079 (8)0.0049 (7)0.0031 (7)
O20.0496 (11)0.0709 (13)0.0668 (12)0.0188 (10)0.0058 (9)0.0268 (11)
O30.0782 (18)0.0683 (17)0.169 (3)0.0155 (14)0.0136 (18)0.0364 (19)
O40.0448 (10)0.0320 (9)0.0596 (10)0.0033 (8)0.0109 (8)0.0014 (8)
O5A0.056 (6)0.058 (5)0.119 (18)0.013 (5)0.017 (7)0.038 (7)
O5B0.092 (8)0.074 (4)0.133 (12)0.025 (4)0.062 (9)0.049 (6)
O60.0515 (10)0.0506 (10)0.0389 (9)0.0057 (9)0.0021 (8)0.0069 (8)
O70.112 (2)0.137 (2)0.0563 (13)0.066 (2)0.0145 (13)0.0068 (15)
O80.0417 (10)0.0378 (9)0.0536 (10)0.0003 (8)0.0025 (8)0.0047 (8)
O90.0424 (10)0.0682 (13)0.0742 (13)0.0098 (10)0.0014 (9)0.0058 (11)
N10.0449 (11)0.0525 (13)0.0459 (12)0.0054 (10)0.0002 (9)0.0154 (10)
N20.0677 (16)0.0561 (14)0.0467 (12)0.0144 (13)0.0027 (11)0.0182 (11)
N30.0596 (14)0.0679 (16)0.0563 (14)0.0044 (13)0.0109 (12)0.0225 (12)
C10.0410 (13)0.0370 (13)0.0446 (13)0.0025 (11)0.0006 (10)0.0039 (10)
C20.0380 (12)0.0318 (12)0.0417 (12)0.0016 (10)0.0010 (10)0.0001 (10)
C30.0451 (14)0.0343 (12)0.0376 (12)0.0065 (10)0.0034 (10)0.0042 (9)
C40.0347 (11)0.0348 (13)0.0441 (12)0.0031 (9)0.0071 (10)0.0003 (10)
C50.0384 (12)0.0427 (14)0.0446 (13)0.0009 (11)0.0006 (10)0.0008 (11)
C60.0491 (15)0.0623 (18)0.0510 (15)0.0115 (14)0.0054 (12)0.0135 (13)
C70.0617 (19)0.071 (2)0.087 (2)0.0219 (18)0.0004 (18)0.0176 (19)
C80.089 (3)0.122 (4)0.135 (4)0.055 (3)0.041 (3)0.036 (3)
C90.068 (2)0.0428 (16)0.106 (3)0.0037 (15)0.032 (2)0.0128 (17)
C100.102 (3)0.0494 (19)0.166 (5)0.024 (2)0.045 (3)0.033 (2)
C110.0415 (14)0.075 (2)0.0430 (14)0.0014 (15)0.0017 (12)0.0047 (14)
C120.0673 (19)0.116 (3)0.0429 (15)0.014 (2)0.0021 (14)0.0133 (16)
C130.0421 (15)0.0462 (15)0.0563 (15)0.0026 (13)0.0099 (12)0.0074 (12)
C140.063 (2)0.071 (2)0.107 (3)0.0025 (17)0.027 (2)0.0204 (19)
C150.0601 (16)0.0452 (15)0.0438 (14)0.0175 (13)0.0091 (12)0.0046 (12)
Geometric parameters (Å, º) top
S1—C151.679 (3)C2—C31.521 (3)
O1—C11.426 (3)C2—H2B0.9800
O1—C51.427 (3)C3—C41.510 (3)
O2—C71.316 (4)C3—H3C0.9800
O2—C61.429 (3)C4—C51.524 (3)
O3—C71.208 (4)C4—H4A0.9800
O4—C91.340 (3)C5—C61.504 (4)
O4—C41.438 (3)C5—H5A0.9800
O5A—C91.240 (14)C6—H6A0.9700
O5B—C91.205 (8)C6—H6B0.9700
O6—C111.345 (3)C7—C81.492 (5)
O6—C31.437 (3)C8—H8A0.9600
O7—C111.181 (4)C8—H8B0.9600
O8—C131.368 (3)C8—H8C0.9600
O8—C21.441 (3)C9—C101.486 (5)
O9—C131.189 (3)C10—H10A0.9600
N1—C151.350 (3)C10—H10B0.9600
N1—C11.414 (3)C10—H10C0.9600
N1—H1A0.8600C11—C121.488 (4)
N2—C151.332 (4)C12—H12A0.9600
N2—N31.395 (4)C12—H12B0.9600
N2—H2A0.8600C12—H12C0.9600
N3—H3A0.8600C13—C141.486 (4)
N3—H3B0.8600C14—H14A0.9600
C1—C21.536 (3)C14—H14B0.9600
C1—H1B0.9800C14—H14C0.9600
C1—O1—C5111.33 (18)C5—C6—H6A110.2
C7—O2—C6116.4 (3)O2—C6—H6B110.2
C9—O4—C4117.8 (2)C5—C6—H6B110.2
C11—O6—C3117.9 (2)H6A—C6—H6B108.5
C13—O8—C2117.7 (2)O3—C7—O2122.4 (3)
C15—N1—C1122.9 (2)O3—C7—C8125.5 (4)
C15—N1—H1A118.6O2—C7—C8111.9 (4)
C1—N1—H1A118.6C7—C8—H8A109.5
C15—N2—N3121.4 (2)C7—C8—H8B109.5
C15—N2—H2A119.3H8A—C8—H8B109.5
N3—N2—H2A119.3C7—C8—H8C109.5
N2—N3—H3A120.0H8A—C8—H8C109.5
N2—N3—H3B120.0H8B—C8—H8C109.5
H3A—N3—H3B120.0O5B—C9—O5A38.8 (8)
N1—C1—O1109.0 (2)O5B—C9—O4123.8 (5)
N1—C1—C2112.9 (2)O5A—C9—O4116.8 (14)
O1—C1—C2107.74 (19)O5B—C9—C10123.1 (5)
N1—C1—H1B109.1O5A—C9—C10123.9 (8)
O1—C1—H1B109.1O4—C9—C10111.3 (3)
C2—C1—H1B109.1C9—C10—H10A109.5
O8—C2—C3106.67 (18)C9—C10—H10B109.5
O8—C2—C1110.41 (19)H10A—C10—H10B109.5
C3—C2—C1107.45 (18)C9—C10—H10C109.5
O8—C2—H2B110.7H10A—C10—H10C109.5
C3—C2—H2B110.7H10B—C10—H10C109.5
C1—C2—H2B110.7O7—C11—O6122.9 (3)
O6—C3—C4108.95 (19)O7—C11—C12125.7 (3)
O6—C3—C2108.92 (19)O6—C11—C12111.3 (3)
C4—C3—C2111.70 (19)C11—C12—H12A109.5
O6—C3—H3C109.1C11—C12—H12B109.5
C4—C3—H3C109.1H12A—C12—H12B109.5
C2—C3—H3C109.1C11—C12—H12C109.5
O4—C4—C3108.75 (19)H12A—C12—H12C109.5
O4—C4—C5109.03 (19)H12B—C12—H12C109.5
C3—C4—C5109.89 (19)O9—C13—O8122.9 (2)
O4—C4—H4A109.7O9—C13—C14126.5 (3)
C3—C4—H4A109.7O8—C13—C14110.6 (3)
C5—C4—H4A109.7C13—C14—H14A109.5
O1—C5—C6104.7 (2)C13—C14—H14B109.5
O1—C5—C4110.48 (19)H14A—C14—H14B109.5
C6—C5—C4113.3 (2)C13—C14—H14C109.5
O1—C5—H5A109.4H14A—C14—H14C109.5
C6—C5—H5A109.4H14B—C14—H14C109.5
C4—C5—H5A109.4N2—C15—N1114.7 (3)
O2—C6—C5107.6 (2)N2—C15—S1121.7 (2)
O2—C6—H6A110.2N1—C15—S1123.5 (2)
C15—N1—C1—O186.2 (3)C1—O1—C5—C6174.4 (2)
C15—N1—C1—C2154.2 (2)C1—O1—C5—C463.3 (3)
C5—O1—C1—N1169.66 (19)O4—C4—C5—O165.6 (3)
C5—O1—C1—C267.5 (2)C3—C4—C5—O153.5 (3)
C13—O8—C2—C3146.7 (2)O4—C4—C5—C651.5 (3)
C13—O8—C2—C196.9 (2)C3—C4—C5—C6170.6 (2)
N1—C1—C2—O861.7 (3)C7—O2—C6—C5152.8 (3)
O1—C1—C2—O8177.87 (18)O1—C5—C6—O2178.2 (2)
N1—C1—C2—C3177.7 (2)C4—C5—C6—O257.7 (3)
O1—C1—C2—C361.9 (2)C6—O2—C7—O32.0 (6)
C11—O6—C3—C4102.1 (2)C6—O2—C7—C8178.0 (3)
C11—O6—C3—C2135.9 (2)C4—O4—C9—O5B14 (2)
O8—C2—C3—O665.6 (2)C4—O4—C9—O5A31 (3)
C1—C2—C3—O6175.96 (18)C4—O4—C9—C10178.8 (3)
O8—C2—C3—C4173.97 (17)C3—O6—C11—O711.2 (4)
C1—C2—C3—C455.6 (3)C3—O6—C11—C12166.9 (2)
C9—O4—C4—C3109.6 (3)C2—O8—C13—O94.3 (4)
C9—O4—C4—C5130.6 (3)C2—O8—C13—C14175.8 (2)
O6—C3—C4—O452.6 (2)N3—N2—C15—N15.7 (4)
C2—C3—C4—O467.8 (2)N3—N2—C15—S1172.9 (2)
O6—C3—C4—C5171.87 (19)C1—N1—C15—N2175.9 (2)
C2—C3—C4—C551.5 (3)C1—N1—C15—S15.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.583.427 (3)168
C12—H12C···O5Bii0.962.313.12 (2)141
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H23N3O9S
Mr421.42
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)7.5445 (11), 8.6792 (13), 31.229 (5)
V3)2044.9 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.30 × 0.14 × 0.11
Data collection
DiffractometerSimens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.940, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
11659, 4041, 3407
Rint0.024
(sin θ/λ)max1)0.618
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.127, 1.02
No. of reflections4041
No. of parameters263
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.25
Absolute structureFlack (1983), 1690 Friedel pairs
Absolute structure parameter0.03 (12)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
S1—C151.679 (3)N1—C11.414 (3)
O1—C11.426 (3)N2—C151.332 (4)
O1—C51.427 (3)N2—N31.395 (4)
N1—C151.350 (3)
N3—N2—C15—N15.7 (4)C1—N1—C15—N2175.9 (2)
N3—N2—C15—S1172.9 (2)C1—N1—C15—S15.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O1i0.862.583.427 (3)168
C12—H12C···O5Bii0.962.313.12 (2)141
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z.
 

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