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Acta Cryst. (2007). E63, o4072
https://doi.org/10.1107/S1600536807044327
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(1S)-Benzyl 3-methyl-5-oxo-4-phen­yl­hydrazono-4,5-dihydro-1H-pyrazole-1-dithiocarboxylate

Y.-H. Liu, Y. Zhao, X.-L. Liu, B.-W. Tong and J. Ye
The title compound, C18H16N4OS2, has been synthesized by the condensation reaction of ethyl 3-oxo-2-(phenyl­hydrazono)­butanoate and (S)-benzyl dithio­carbazate. The pyrazolone structure is stabilized by a strong N—H...O=C intra­molecular hydrogen bond.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044327/lw2028sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044327/lw2028Isup2.hkl
Contains datablock I

CCDC reference: 663776

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        600 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Pyrazolones constitute a group of organic compounds that have been extensively studied due to their properties and applications. Since the synthesis of antipyrine (2,3-dimethyl-1-phenyl-5-pyrazolone) by Knorr (Knorr,1884), a great deal of attention has been paid to the properties of these compounds and a series of drugs have been synthesized. For examples anti-inflammatory drugs (Clark & Bookland, 2005), compounds with antifungal compounds (Omotowa & Mesubi, 1997), antitumor (Caruso et al., 2000) and antihyperglycemic (Kees et al., 1996). Although the use of pyrazolones as drugs has warranted significant attention, many more applications have been devised for this group of molecules outside the pharmaceutical field. They have been applied to the solvent extraction of metal ions (Bose et al., 2005), for analytical purposes (Ito et al., 2001), in the preparation of azo colorants (Whitaker, 1995), as ligands in complexes with catalytic activity (Bao et al., 2006) and in the synthesis of rare earth metal complexes with interesting photophysical properties (Shi et al., 2005). In present work, we report the preparation the title compound (I), and its crystal structure.

Determination of its crystal structure (Fig.1), the title compound shows one larger conjugation system in the molecule with eight carbon atoms (C11–C18),four nitrogen atoms (N1–N4) and one oxygen (O1),which is further confirmed by by UV spectroscopy.

In the title compound, the dihedral angle between this conjugation system with plane of C7—S1—C8═S2 is 13.1°. The benzene ring (C13–C18) is involved in the conjugation system (Table 1). An intramolecular N—H···O═ C hydrogen bonds is also present in the crystal structure of (I) (Table 2).

Related literature top

For related literature, see: Bao et al. (2006); Bose et al. (2005); Caruso et al. (2000); Clark & Bookland (2005); Ito et al. (2001); Kees et al. (1996); Knorr (1884); Omotowa & Mesubi (1997); Shi et al. (2005); Whitaker (1995).

Experimental top

The title compound was synthesized by refluxing an ethanol solution of ethyl 3-oxo-2-(phenylhydrazono)butanate and S-benzyldithiocarbazate (1:1) for 24 h. After 12 h at room temperature for 12 h, The precipitatewas colleceted by filtration and recrystallized from ethanol (yield 82.2%)·The yellow crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane solution at 278 K (m.p. 344.1–345.8 K). Analysis calculated for C18H16N4OS2: C 58.67, H 4.36, N 15.21%; found: C 58.66, H 4.35, N 15.21%. IR (KBr,cm-1): 3214(s, NH), 1619 (versus, O═C), 1545 (s, N═C), 1280(w, S═C). UV (λmax, in CHCl3, nm): 404 (K-band, 1.92× 104). 1HNMR (600 MHz, CDCl3): δ: 10.47 (m, 10H, ArH), 6.83 (s, H, NH), 4.06 (s, 2H, ArCH2), 1.19 (s, 3H, CH3).

Refinement top

The H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(methyl C) except for N4, (N—H = 0.90 Å), which was refined.

Structure description top

Pyrazolones constitute a group of organic compounds that have been extensively studied due to their properties and applications. Since the synthesis of antipyrine (2,3-dimethyl-1-phenyl-5-pyrazolone) by Knorr (Knorr,1884), a great deal of attention has been paid to the properties of these compounds and a series of drugs have been synthesized. For examples anti-inflammatory drugs (Clark & Bookland, 2005), compounds with antifungal compounds (Omotowa & Mesubi, 1997), antitumor (Caruso et al., 2000) and antihyperglycemic (Kees et al., 1996). Although the use of pyrazolones as drugs has warranted significant attention, many more applications have been devised for this group of molecules outside the pharmaceutical field. They have been applied to the solvent extraction of metal ions (Bose et al., 2005), for analytical purposes (Ito et al., 2001), in the preparation of azo colorants (Whitaker, 1995), as ligands in complexes with catalytic activity (Bao et al., 2006) and in the synthesis of rare earth metal complexes with interesting photophysical properties (Shi et al., 2005). In present work, we report the preparation the title compound (I), and its crystal structure.

Determination of its crystal structure (Fig.1), the title compound shows one larger conjugation system in the molecule with eight carbon atoms (C11–C18),four nitrogen atoms (N1–N4) and one oxygen (O1),which is further confirmed by by UV spectroscopy.

In the title compound, the dihedral angle between this conjugation system with plane of C7—S1—C8═S2 is 13.1°. The benzene ring (C13–C18) is involved in the conjugation system (Table 1). An intramolecular N—H···O═ C hydrogen bonds is also present in the crystal structure of (I) (Table 2).

For related literature, see: Bao et al. (2006); Bose et al. (2005); Caruso et al. (2000); Clark & Bookland (2005); Ito et al. (2001); Kees et al. (1996); Knorr (1884); Omotowa & Mesubi (1997); Shi et al. (2005); Whitaker (1995).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. The dashed line indicates the intramolecular hydrogen bond.
(1S)-Benzyl 3-methyl-5-oxo-4-phenylhydrazono-4,5-dihydro-1H-pyrazole-1-dithiocarboxylate top
Crystal data top
C18H16N4OS2Z = 2
Mr = 368.47F(000) = 384
Triclinic, P1Dx = 1.359 Mg m−3
a = 9.143 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.079 (6) ÅCell parameters from 1587 reflections
c = 10.217 (6) Åθ = 2.8–28.1°
α = 84.059 (10)°µ = 0.31 mm−1
β = 79.410 (11)°T = 294 K
γ = 77.095 (9)°Prism, yellow
V = 900.2 (10) Å30.24 × 0.22 × 0.16 mm
Data collection top
Bruker SMART CCD area detector
diffractometer		3062 independent reflections
Radiation source: fine-focus sealed tube1974 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker 2001)		h = −10→10
Tmin = 0.930, Tmax = 0.952k = −11→11
4385 measured reflectionsl = −12→5
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.22P]
where P = (Fo2 + 2Fc2)/3
3062 reflections(Δ/σ)max = 0.001
231 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C18H16N4OS2γ = 77.095 (9)°
Mr = 368.47V = 900.2 (10) Å3
Triclinic, P1Z = 2
a = 9.143 (6) ÅMo Kα radiation
b = 10.079 (6) ŵ = 0.31 mm−1
c = 10.217 (6) ÅT = 294 K
α = 84.059 (10)°0.24 × 0.22 × 0.16 mm
β = 79.410 (11)°
Data collection top
Bruker SMART CCD area detector
diffractometer		3062 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker 2001)		1974 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.952Rint = 0.034
4385 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.25 e Å−3
3062 reflectionsΔρmin = −0.24 e Å−3
231 parameters
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*/Ueq
S10.33476 (11)0.39781 (8)0.74742 (8)0.0596 (3)
S20.44038 (11)0.13389 (8)0.60963 (9)0.0608 (3)
O10.6843 (2)−0.0198 (2)0.7830 (2)0.0559 (6)
N10.5025 (3)0.1812 (2)0.8440 (2)0.0447 (6)
N20.4614 (3)0.2616 (2)0.9587 (2)0.0483 (7)
N40.8444 (3)−0.1042 (2)0.9988 (3)0.0468 (7)
H40.834 (4)−0.121 (3)0.916 (3)0.060 (10)*
N30.7573 (3)0.0034 (2)1.0579 (2)0.0457 (6)
C10.2451 (4)0.6887 (3)0.5723 (3)0.0569 (9)
H10.35050.67130.54980.068*
C20.1642 (4)0.8227 (3)0.5820 (3)0.0603 (9)
H20.21560.89410.56750.072*
C30.0083 (4)0.8492 (3)0.6129 (3)0.0585 (10)
H3−0.04560.93870.62040.070*
C4−0.0681 (4)0.7445 (4)0.6329 (3)0.0593 (10)
H4A−0.17380.76300.65090.071*
C50.0129 (4)0.6110 (3)0.6263 (3)0.0570 (9)
H5−0.03890.53990.64250.068*
C60.1716 (4)0.5822 (3)0.5954 (3)0.0469 (8)
C70.2581 (4)0.4350 (3)0.5920 (3)0.0625 (10)
H7A0.33960.42380.51580.075*
H7B0.19060.37470.58640.075*
C80.4323 (3)0.2265 (3)0.7332 (3)0.0418 (7)
C90.6219 (3)0.0678 (3)0.8612 (3)0.0445 (8)
C100.6526 (3)0.0813 (3)0.9940 (3)0.0425 (7)
C110.5485 (3)0.2025 (3)1.0448 (3)0.0437 (7)
C120.5357 (4)0.2564 (3)1.1777 (3)0.0638 (10)
H12A0.63280.27121.18850.096*
H12B0.50360.19161.24660.096*
H12C0.46230.34101.18370.096*
C130.9598 (3)−0.1901 (3)1.0616 (3)0.0428 (7)
C141.0467 (4)−0.3042 (3)0.9965 (3)0.0541 (9)
H141.0282−0.32270.91440.065*
C151.1615 (4)−0.3898 (3)1.0562 (3)0.0573 (9)
H151.2187−0.46691.01450.069*
C161.1911 (4)−0.3614 (3)1.1758 (3)0.0572 (9)
H161.2703−0.41741.21330.069*
C171.1033 (4)−0.2496 (3)1.2406 (3)0.0573 (9)
H171.1220−0.23181.32280.069*
C180.9873 (4)−0.1637 (3)1.1837 (3)0.0511 (8)
H180.9283−0.08861.22770.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0772 (7)0.0387 (5)0.0614 (5)0.0107 (4)−0.0292 (5)−0.0144 (4)
S20.0757 (7)0.0447 (5)0.0598 (5)0.0029 (4)−0.0162 (5)−0.0183 (4)
O10.0515 (14)0.0453 (12)0.0669 (14)0.0049 (11)−0.0095 (11)−0.0186 (11)
N10.0448 (15)0.0350 (13)0.0510 (15)0.0026 (12)−0.0093 (12)−0.0085 (11)
N20.0509 (16)0.0380 (14)0.0539 (15)−0.0009 (12)−0.0094 (13)−0.0112 (12)
N40.0443 (16)0.0416 (15)0.0530 (16)−0.0007 (12)−0.0127 (14)−0.0058 (12)
N30.0385 (15)0.0403 (14)0.0558 (15)−0.0055 (12)−0.0062 (13)−0.0003 (12)
C10.048 (2)0.057 (2)0.065 (2)−0.0052 (18)−0.0161 (18)−0.0035 (17)
C20.070 (3)0.0450 (19)0.067 (2)−0.0127 (19)−0.015 (2)−0.0014 (16)
C30.071 (3)0.0417 (19)0.057 (2)0.0040 (19)−0.0124 (19)−0.0039 (15)
C40.048 (2)0.062 (2)0.062 (2)0.0038 (19)−0.0079 (17)−0.0162 (17)
C50.065 (2)0.0486 (19)0.060 (2)−0.0138 (18)−0.0120 (18)−0.0068 (16)
C60.053 (2)0.0397 (17)0.0463 (17)0.0023 (16)−0.0168 (16)−0.0068 (13)
C70.073 (2)0.0491 (19)0.064 (2)0.0084 (18)−0.0283 (19)−0.0128 (16)
C80.0382 (17)0.0370 (16)0.0494 (17)−0.0064 (14)−0.0067 (14)−0.0037 (13)
C90.0366 (18)0.0368 (17)0.0585 (19)−0.0066 (14)−0.0042 (15)−0.0049 (14)
C100.0375 (18)0.0363 (16)0.0526 (18)−0.0071 (14)−0.0061 (15)−0.0011 (13)
C110.0427 (18)0.0392 (16)0.0492 (18)−0.0072 (15)−0.0085 (15)−0.0053 (13)
C120.069 (2)0.061 (2)0.061 (2)−0.0040 (19)−0.0133 (19)−0.0182 (17)
C130.0380 (18)0.0399 (17)0.0496 (18)−0.0082 (14)−0.0077 (15)0.0020 (13)
C140.059 (2)0.0480 (19)0.0540 (19)−0.0034 (17)−0.0136 (17)−0.0090 (15)
C150.059 (2)0.0425 (18)0.063 (2)0.0062 (17)−0.0100 (18)−0.0073 (15)
C160.050 (2)0.054 (2)0.060 (2)0.0001 (17)−0.0096 (17)0.0084 (16)
C170.059 (2)0.061 (2)0.0515 (19)−0.0065 (18)−0.0160 (17)−0.0034 (16)
C180.048 (2)0.0502 (19)0.0519 (18)−0.0014 (16)−0.0087 (16)−0.0095 (14)
Geometric parameters (Å, º) top
S1—C81.765 (3)C5—H50.9300
S1—C71.823 (3)C6—C71.518 (4)
S2—C81.628 (3)C7—H7A0.9700
O1—C91.223 (3)C7—H7B0.9700
N1—C81.390 (4)C9—C101.460 (4)
N1—C91.415 (3)C10—C111.448 (4)
N1—N21.439 (3)C11—C121.489 (4)
N2—C111.303 (4)C12—H12A0.9600
N4—N31.322 (3)C12—H12B0.9600
N4—C131.414 (4)C12—H12C0.9600
N4—H40.90 (3)C13—C181.380 (4)
N3—C101.322 (4)C13—C141.397 (4)
C1—C61.368 (5)C14—C151.393 (4)
C1—C21.391 (4)C14—H140.9300
C1—H10.9300C15—C161.369 (5)
C2—C31.373 (5)C15—H150.9300
C2—H20.9300C16—C171.381 (4)
C3—C41.369 (5)C16—H160.9300
C3—H30.9300C17—C181.387 (4)
C4—C51.385 (4)C17—H170.9300
C4—H4A0.9300C18—H180.9300
C5—C61.397 (5)
C8—S1—C7101.82 (14)S2—C8—S1125.74 (18)
C8—N1—C9129.6 (2)O1—C9—N1128.1 (3)
C8—N1—N2119.0 (2)O1—C9—C10128.7 (3)
C9—N1—N2111.3 (2)N1—C9—C10103.2 (2)
C11—N2—N1107.2 (2)N3—C10—C11124.6 (3)
N3—N4—C13120.3 (3)N3—C10—C9128.4 (3)
N3—N4—H4120 (2)C11—C10—C9107.0 (2)
C13—N4—H4119 (2)N2—C11—C10111.2 (3)
N4—N3—C10117.7 (3)N2—C11—C12122.2 (3)
C6—C1—C2120.9 (3)C10—C11—C12126.5 (3)
C6—C1—H1119.5C11—C12—H12A109.5
C2—C1—H1119.5C11—C12—H12B109.5
C3—C2—C1119.8 (4)H12A—C12—H12B109.5
C3—C2—H2120.1C11—C12—H12C109.5
C1—C2—H2120.1H12A—C12—H12C109.5
C4—C3—C2120.3 (3)H12B—C12—H12C109.5
C4—C3—H3119.8C18—C13—C14120.2 (3)
C2—C3—H3119.8C18—C13—N4121.7 (3)
C3—C4—C5119.7 (3)C14—C13—N4118.1 (3)
C3—C4—H4A120.2C15—C14—C13119.0 (3)
C5—C4—H4A120.2C15—C14—H14120.5
C4—C5—C6120.7 (3)C13—C14—H14120.5
C4—C5—H5119.7C16—C15—C14120.6 (3)
C6—C5—H5119.7C16—C15—H15119.7
C1—C6—C5118.5 (3)C14—C15—H15119.7
C1—C6—C7121.7 (3)C15—C16—C17120.0 (3)
C5—C6—C7119.8 (3)C15—C16—H16120.0
C6—C7—S1105.5 (2)C17—C16—H16120.0
C6—C7—H7A110.6C16—C17—C18120.4 (3)
S1—C7—H7A110.6C16—C17—H17119.8
C6—C7—H7B110.6C18—C17—H17119.8
S1—C7—H7B110.6C13—C18—C17119.7 (3)
H7A—C7—H7B108.8C13—C18—H18120.1
N1—C8—S2124.5 (2)C17—C18—H18120.1
N1—C8—S1109.79 (19)
C8—N1—N2—C11−176.3 (3)N2—N1—C9—C100.3 (3)
C9—N1—N2—C11−0.4 (3)N4—N3—C10—C11−179.9 (3)
C13—N4—N3—C10179.1 (3)N4—N3—C10—C9−2.3 (5)
C6—C1—C2—C3−1.1 (5)O1—C9—C10—N31.6 (6)
C1—C2—C3—C4−0.7 (5)N1—C9—C10—N3−178.0 (3)
C2—C3—C4—C52.2 (5)O1—C9—C10—C11179.6 (3)
C3—C4—C5—C6−1.9 (5)N1—C9—C10—C11−0.1 (3)
C2—C1—C6—C51.4 (5)N1—N2—C11—C100.4 (3)
C2—C1—C6—C7−177.0 (3)N1—N2—C11—C12−178.8 (3)
C4—C5—C6—C10.1 (5)N3—C10—C11—N2177.8 (3)
C4—C5—C6—C7178.5 (3)C9—C10—C11—N2−0.2 (4)
C1—C6—C7—S175.7 (3)N3—C10—C11—C12−3.1 (5)
C5—C6—C7—S1−102.7 (3)C9—C10—C11—C12178.9 (3)
C8—S1—C7—C6−179.9 (2)N3—N4—C13—C18−1.4 (5)
C9—N1—C8—S218.1 (5)N3—N4—C13—C14178.6 (3)
N2—N1—C8—S2−167.0 (2)C18—C13—C14—C15−0.4 (5)
C9—N1—C8—S1−161.8 (3)N4—C13—C14—C15179.6 (3)
N2—N1—C8—S113.1 (3)C13—C14—C15—C16−1.3 (5)
C7—S1—C8—N1178.5 (2)C14—C15—C16—C172.2 (5)
C7—S1—C8—S2−1.4 (3)C15—C16—C17—C18−1.6 (5)
C8—N1—C9—O1−4.1 (5)C14—C13—C18—C171.1 (5)
N2—N1—C9—O1−179.3 (3)N4—C13—C18—C17−178.9 (3)
C8—N1—C9—C10175.6 (3)C16—C17—C18—C13−0.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.90 (3)2.13 (3)2.823 (4)133 (3)

Experimental details

Crystal data
Chemical formulaC18H16N4OS2
Mr368.47
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.143 (6), 10.079 (6), 10.217 (6)
α, β, γ (°)84.059 (10), 79.410 (11), 77.095 (9)
V (Å3)900.2 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.24 × 0.22 × 0.16
Data collection
DiffractometerBruker SMART CCD area detector
Absorption correctionMulti-scan
(SADABS; Bruker 2001)
Tmin, Tmax0.930, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections		4385, 3062, 1974
Rint0.034
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.120, 1.03
No. of reflections3062
No. of parameters231
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.25, −0.24

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top
S1—C81.765 (3)N4—N31.322 (3)
S1—C71.823 (3)N4—C131.414 (4)
S2—C81.628 (3)N3—C101.322 (4)
O1—C91.223 (3)C6—C71.518 (4)
N1—C81.390 (4)C9—C101.460 (4)
N1—C91.415 (3)C10—C111.448 (4)
N1—N21.439 (3)C11—C121.489 (4)
N2—C111.303 (4)
C8—S1—C7101.82 (14)O1—C9—N1128.1 (3)
C8—N1—C9129.6 (2)O1—C9—C10128.7 (3)
C8—N1—N2119.0 (2)N1—C9—C10103.2 (2)
C9—N1—N2111.3 (2)N3—C10—C11124.6 (3)
C11—N2—N1107.2 (2)N3—C10—C9128.4 (3)
N3—N4—C13120.3 (3)C11—C10—C9107.0 (2)
N4—N3—C10117.7 (3)N2—C11—C10111.2 (3)
C1—C6—C7121.7 (3)N2—C11—C12122.2 (3)
C6—C7—S1105.5 (2)C10—C11—C12126.5 (3)
N1—C8—S1109.79 (19)C18—C13—N4121.7 (3)
S2—C8—S1125.74 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O10.90 (3)2.13 (3)2.823 (4)133 (3)
 

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