(1S)-Benzyl 3-methyl-5-oxo-4-phen­yl­hydrazono-4,5-dihydro-1H-pyrazole-1-dithiocarboxylate

Liu, Y.-H.; Zhao, Y.; Liu, X.-L.; Tong, B.-W.; Ye, J.

doi:10.1107/S1600536807044327

(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

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044327/lw2028sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044327/lw2028Isup2.hkl Contains datablock I

CCDC reference: 663776

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (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 (λ_max, 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).

Structure description top

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

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

C₁₈H₁₆N₄OS₂	Z = 2
M_r = 368.47	F(000) = 384
Triclinic, P1	D_x = 1.359 Mg m⁻³
a = 9.143 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.079 (6) Å	Cell parameters from 1587 reflections
c = 10.217 (6) Å	θ = 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) Å³	0.24 × 0.22 × 0.16 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3062 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker 2001)	h = −10→10
T_min = 0.930, T_max = 0.952	k = −11→11
4385 measured reflections	l = −12→5

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0469P)² + 0.22P] where P = (F_o² + 2F_c²)/3
3062 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₆N₄OS₂	γ = 77.095 (9)°
M_r = 368.47	V = 900.2 (10) Å³
Triclinic, P1	Z = 2
a = 9.143 (6) Å	Mo Kα radiation
b = 10.079 (6) Å	µ = 0.31 mm⁻¹
c = 10.217 (6) Å	T = 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)
T_min = 0.930, T_max = 0.952	R_int = 0.034
4385 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
3062 reflections	Δρ_min = −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

	x	y	z	U_iso*/U_eq
S1	0.33476 (11)	0.39781 (8)	0.74742 (8)	0.0596 (3)
S2	0.44038 (11)	0.13389 (8)	0.60963 (9)	0.0608 (3)
O1	0.6843 (2)	−0.0198 (2)	0.7830 (2)	0.0559 (6)
N1	0.5025 (3)	0.1812 (2)	0.8440 (2)	0.0447 (6)
N2	0.4614 (3)	0.2616 (2)	0.9587 (2)	0.0483 (7)
N4	0.8444 (3)	−0.1042 (2)	0.9988 (3)	0.0468 (7)
H4	0.834 (4)	−0.121 (3)	0.916 (3)	0.060 (10)*
N3	0.7573 (3)	0.0034 (2)	1.0579 (2)	0.0457 (6)
C1	0.2451 (4)	0.6887 (3)	0.5723 (3)	0.0569 (9)
H1	0.3505	0.6713	0.5498	0.068*
C2	0.1642 (4)	0.8227 (3)	0.5820 (3)	0.0603 (9)
H2	0.2156	0.8941	0.5675	0.072*
C3	0.0083 (4)	0.8492 (3)	0.6129 (3)	0.0585 (10)
H3	−0.0456	0.9387	0.6204	0.070*
C4	−0.0681 (4)	0.7445 (4)	0.6329 (3)	0.0593 (10)
H4A	−0.1738	0.7630	0.6509	0.071*
C5	0.0129 (4)	0.6110 (3)	0.6263 (3)	0.0570 (9)
H5	−0.0389	0.5399	0.6425	0.068*
C6	0.1716 (4)	0.5822 (3)	0.5954 (3)	0.0469 (8)
C7	0.2581 (4)	0.4350 (3)	0.5920 (3)	0.0625 (10)
H7A	0.3396	0.4238	0.5158	0.075*
H7B	0.1906	0.3747	0.5864	0.075*
C8	0.4323 (3)	0.2265 (3)	0.7332 (3)	0.0418 (7)
C9	0.6219 (3)	0.0678 (3)	0.8612 (3)	0.0445 (8)
C10	0.6526 (3)	0.0813 (3)	0.9940 (3)	0.0425 (7)
C11	0.5485 (3)	0.2025 (3)	1.0448 (3)	0.0437 (7)
C12	0.5357 (4)	0.2564 (3)	1.1777 (3)	0.0638 (10)
H12A	0.6328	0.2712	1.1885	0.096*
H12B	0.5036	0.1916	1.2466	0.096*
H12C	0.4623	0.3410	1.1837	0.096*
C13	0.9598 (3)	−0.1901 (3)	1.0616 (3)	0.0428 (7)
C14	1.0467 (4)	−0.3042 (3)	0.9965 (3)	0.0541 (9)
H14	1.0282	−0.3227	0.9144	0.065*
C15	1.1615 (4)	−0.3898 (3)	1.0562 (3)	0.0573 (9)
H15	1.2187	−0.4669	1.0145	0.069*
C16	1.1911 (4)	−0.3614 (3)	1.1758 (3)	0.0572 (9)
H16	1.2703	−0.4174	1.2133	0.069*
C17	1.1033 (4)	−0.2496 (3)	1.2406 (3)	0.0573 (9)
H17	1.1220	−0.2318	1.3228	0.069*
C18	0.9873 (4)	−0.1637 (3)	1.1837 (3)	0.0511 (8)
H18	0.9283	−0.0886	1.2277	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0772 (7)	0.0387 (5)	0.0614 (5)	0.0107 (4)	−0.0292 (5)	−0.0144 (4)
S2	0.0757 (7)	0.0447 (5)	0.0598 (5)	0.0029 (4)	−0.0162 (5)	−0.0183 (4)
O1	0.0515 (14)	0.0453 (12)	0.0669 (14)	0.0049 (11)	−0.0095 (11)	−0.0186 (11)
N1	0.0448 (15)	0.0350 (13)	0.0510 (15)	0.0026 (12)	−0.0093 (12)	−0.0085 (11)
N2	0.0509 (16)	0.0380 (14)	0.0539 (15)	−0.0009 (12)	−0.0094 (13)	−0.0112 (12)
N4	0.0443 (16)	0.0416 (15)	0.0530 (16)	−0.0007 (12)	−0.0127 (14)	−0.0058 (12)
N3	0.0385 (15)	0.0403 (14)	0.0558 (15)	−0.0055 (12)	−0.0062 (13)	−0.0003 (12)
C1	0.048 (2)	0.057 (2)	0.065 (2)	−0.0052 (18)	−0.0161 (18)	−0.0035 (17)
C2	0.070 (3)	0.0450 (19)	0.067 (2)	−0.0127 (19)	−0.015 (2)	−0.0014 (16)
C3	0.071 (3)	0.0417 (19)	0.057 (2)	0.0040 (19)	−0.0124 (19)	−0.0039 (15)
C4	0.048 (2)	0.062 (2)	0.062 (2)	0.0038 (19)	−0.0079 (17)	−0.0162 (17)
C5	0.065 (2)	0.0486 (19)	0.060 (2)	−0.0138 (18)	−0.0120 (18)	−0.0068 (16)
C6	0.053 (2)	0.0397 (17)	0.0463 (17)	0.0023 (16)	−0.0168 (16)	−0.0068 (13)
C7	0.073 (2)	0.0491 (19)	0.064 (2)	0.0084 (18)	−0.0283 (19)	−0.0128 (16)
C8	0.0382 (17)	0.0370 (16)	0.0494 (17)	−0.0064 (14)	−0.0067 (14)	−0.0037 (13)
C9	0.0366 (18)	0.0368 (17)	0.0585 (19)	−0.0066 (14)	−0.0042 (15)	−0.0049 (14)
C10	0.0375 (18)	0.0363 (16)	0.0526 (18)	−0.0071 (14)	−0.0061 (15)	−0.0011 (13)
C11	0.0427 (18)	0.0392 (16)	0.0492 (18)	−0.0072 (15)	−0.0085 (15)	−0.0053 (13)
C12	0.069 (2)	0.061 (2)	0.061 (2)	−0.0040 (19)	−0.0133 (19)	−0.0182 (17)
C13	0.0380 (18)	0.0399 (17)	0.0496 (18)	−0.0082 (14)	−0.0077 (15)	0.0020 (13)
C14	0.059 (2)	0.0480 (19)	0.0540 (19)	−0.0034 (17)	−0.0136 (17)	−0.0090 (15)
C15	0.059 (2)	0.0425 (18)	0.063 (2)	0.0062 (17)	−0.0100 (18)	−0.0073 (15)
C16	0.050 (2)	0.054 (2)	0.060 (2)	0.0001 (17)	−0.0096 (17)	0.0084 (16)
C17	0.059 (2)	0.061 (2)	0.0515 (19)	−0.0065 (18)	−0.0160 (17)	−0.0034 (16)
C18	0.048 (2)	0.0502 (19)	0.0519 (18)	−0.0014 (16)	−0.0087 (16)	−0.0095 (14)

Geometric parameters (Å, º) top

S1—C8	1.765 (3)	C5—H5	0.9300
S1—C7	1.823 (3)	C6—C7	1.518 (4)
S2—C8	1.628 (3)	C7—H7A	0.9700
O1—C9	1.223 (3)	C7—H7B	0.9700
N1—C8	1.390 (4)	C9—C10	1.460 (4)
N1—C9	1.415 (3)	C10—C11	1.448 (4)
N1—N2	1.439 (3)	C11—C12	1.489 (4)
N2—C11	1.303 (4)	C12—H12A	0.9600
N4—N3	1.322 (3)	C12—H12B	0.9600
N4—C13	1.414 (4)	C12—H12C	0.9600
N4—H4	0.90 (3)	C13—C18	1.380 (4)
N3—C10	1.322 (4)	C13—C14	1.397 (4)
C1—C6	1.368 (5)	C14—C15	1.393 (4)
C1—C2	1.391 (4)	C14—H14	0.9300
C1—H1	0.9300	C15—C16	1.369 (5)
C2—C3	1.373 (5)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.381 (4)
C3—C4	1.369 (5)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.387 (4)
C4—C5	1.385 (4)	C17—H17	0.9300
C4—H4A	0.9300	C18—H18	0.9300
C5—C6	1.397 (5)

C8—S1—C7	101.82 (14)	S2—C8—S1	125.74 (18)
C8—N1—C9	129.6 (2)	O1—C9—N1	128.1 (3)
C8—N1—N2	119.0 (2)	O1—C9—C10	128.7 (3)
C9—N1—N2	111.3 (2)	N1—C9—C10	103.2 (2)
C11—N2—N1	107.2 (2)	N3—C10—C11	124.6 (3)
N3—N4—C13	120.3 (3)	N3—C10—C9	128.4 (3)
N3—N4—H4	120 (2)	C11—C10—C9	107.0 (2)
C13—N4—H4	119 (2)	N2—C11—C10	111.2 (3)
N4—N3—C10	117.7 (3)	N2—C11—C12	122.2 (3)
C6—C1—C2	120.9 (3)	C10—C11—C12	126.5 (3)
C6—C1—H1	119.5	C11—C12—H12A	109.5
C2—C1—H1	119.5	C11—C12—H12B	109.5
C3—C2—C1	119.8 (4)	H12A—C12—H12B	109.5
C3—C2—H2	120.1	C11—C12—H12C	109.5
C1—C2—H2	120.1	H12A—C12—H12C	109.5
C4—C3—C2	120.3 (3)	H12B—C12—H12C	109.5
C4—C3—H3	119.8	C18—C13—C14	120.2 (3)
C2—C3—H3	119.8	C18—C13—N4	121.7 (3)
C3—C4—C5	119.7 (3)	C14—C13—N4	118.1 (3)
C3—C4—H4A	120.2	C15—C14—C13	119.0 (3)
C5—C4—H4A	120.2	C15—C14—H14	120.5
C4—C5—C6	120.7 (3)	C13—C14—H14	120.5
C4—C5—H5	119.7	C16—C15—C14	120.6 (3)
C6—C5—H5	119.7	C16—C15—H15	119.7
C1—C6—C5	118.5 (3)	C14—C15—H15	119.7
C1—C6—C7	121.7 (3)	C15—C16—C17	120.0 (3)
C5—C6—C7	119.8 (3)	C15—C16—H16	120.0
C6—C7—S1	105.5 (2)	C17—C16—H16	120.0
C6—C7—H7A	110.6	C16—C17—C18	120.4 (3)
S1—C7—H7A	110.6	C16—C17—H17	119.8
C6—C7—H7B	110.6	C18—C17—H17	119.8
S1—C7—H7B	110.6	C13—C18—C17	119.7 (3)
H7A—C7—H7B	108.8	C13—C18—H18	120.1
N1—C8—S2	124.5 (2)	C17—C18—H18	120.1
N1—C8—S1	109.79 (19)

C8—N1—N2—C11	−176.3 (3)	N2—N1—C9—C10	0.3 (3)
C9—N1—N2—C11	−0.4 (3)	N4—N3—C10—C11	−179.9 (3)
C13—N4—N3—C10	179.1 (3)	N4—N3—C10—C9	−2.3 (5)
C6—C1—C2—C3	−1.1 (5)	O1—C9—C10—N3	1.6 (6)
C1—C2—C3—C4	−0.7 (5)	N1—C9—C10—N3	−178.0 (3)
C2—C3—C4—C5	2.2 (5)	O1—C9—C10—C11	179.6 (3)
C3—C4—C5—C6	−1.9 (5)	N1—C9—C10—C11	−0.1 (3)
C2—C1—C6—C5	1.4 (5)	N1—N2—C11—C10	0.4 (3)
C2—C1—C6—C7	−177.0 (3)	N1—N2—C11—C12	−178.8 (3)
C4—C5—C6—C1	0.1 (5)	N3—C10—C11—N2	177.8 (3)
C4—C5—C6—C7	178.5 (3)	C9—C10—C11—N2	−0.2 (4)
C1—C6—C7—S1	75.7 (3)	N3—C10—C11—C12	−3.1 (5)
C5—C6—C7—S1	−102.7 (3)	C9—C10—C11—C12	178.9 (3)
C8—S1—C7—C6	−179.9 (2)	N3—N4—C13—C18	−1.4 (5)
C9—N1—C8—S2	18.1 (5)	N3—N4—C13—C14	178.6 (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—C15	179.6 (3)
N2—N1—C8—S1	13.1 (3)	C13—C14—C15—C16	−1.3 (5)
C7—S1—C8—N1	178.5 (2)	C14—C15—C16—C17	2.2 (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—C17	1.1 (5)
N2—N1—C9—O1	−179.3 (3)	N4—C13—C18—C17	−178.9 (3)
C8—N1—C9—C10	175.6 (3)	C16—C17—C18—C13	−0.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.90 (3)	2.13 (3)	2.823 (4)	133 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₄OS₂
M_r	368.47
Crystal system, space group	Triclinic, 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)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker 2001)
T_min, T_max	0.930, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	4385, 3062, 1974
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.03
No. of reflections	3062
No. of parameters	231
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (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—C8	1.765 (3)	N4—N3	1.322 (3)
S1—C7	1.823 (3)	N4—C13	1.414 (4)
S2—C8	1.628 (3)	N3—C10	1.322 (4)
O1—C9	1.223 (3)	C6—C7	1.518 (4)
N1—C8	1.390 (4)	C9—C10	1.460 (4)
N1—C9	1.415 (3)	C10—C11	1.448 (4)
N1—N2	1.439 (3)	C11—C12	1.489 (4)
N2—C11	1.303 (4)

C8—S1—C7	101.82 (14)	O1—C9—N1	128.1 (3)
C8—N1—C9	129.6 (2)	O1—C9—C10	128.7 (3)
C8—N1—N2	119.0 (2)	N1—C9—C10	103.2 (2)
C9—N1—N2	111.3 (2)	N3—C10—C11	124.6 (3)
C11—N2—N1	107.2 (2)	N3—C10—C9	128.4 (3)
N3—N4—C13	120.3 (3)	C11—C10—C9	107.0 (2)
N4—N3—C10	117.7 (3)	N2—C11—C10	111.2 (3)
C1—C6—C7	121.7 (3)	N2—C11—C12	122.2 (3)
C6—C7—S1	105.5 (2)	C10—C11—C12	126.5 (3)
N1—C8—S1	109.79 (19)	C18—C13—N4	121.7 (3)
S2—C8—S1	125.74 (18)