N′-(3-Sulfanyl­idene-3,4-di­hydro­quinoxalin-2-yl)benzohydrazide di­methyl­formamide monosolvate

Zanzoul, A.; Essassi, E.M.; Pratviel, G.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536813019181

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1268

doi:10.1107/S1600536813019181

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N′-(3-Sulfanylidene-3,4-dihydroquinoxalin-2-yl)benzohydrazide dimethylformamide monosolvate

Asmae Zanzoul,^a,^b ^* El Mokhtar Essassi,^a Geneviève Pratviel,^b Mohamed Saadi ^c and Lahcen El Ammari ^c

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue, Ibn Batouta, Rabat, Morocco, ^bLaboratoire de Chimie de Coordination du CNRS 205, Route de Narbonne 31077, Toulouse, France, and ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: a_zanzoul@yahoo.fr

(Received 28 June 2013; accepted 10 July 2013; online 17 July 2013)

The 2-sulfanylidene-3,4-dihydroquinoxalin-2-yl ring system of the title solvate, C₁₅H₁₂N₄OS·C₃H₇NO, is essentially planar, the maximum deviation from the mean plane being 0.024 (2) Å for the thione C atom. The mean plane through the fused-ring system is almost perpendicular to the terminal phenyl ring, as indicated by the dihedral angle of 70.05 (8)°. In the crystal, the main and solvent molecules are linked by N—H⋯O hydrogen bonds, forming a layer parallel to (010).

Related literature

For potential applications of quinoxaline derivatives, see: Cheon et al. (2004 ); Jackson et al. (1991 ); Benzeid et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₂N₄OS·C₃H₇NO
M_r = 369.44
Monoclinic, P 2₁ /c
a = 10.4053 (2) Å
b = 16.8563 (5) Å
c = 10.3624 (2) Å
β = 100.882 (2)°
V = 1784.83 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 180 K
0.20 × 0.12 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2012 $[Oxford Diffraction (2012). Oxford Diffraction Ltd, Yarnton,England.]$ ) T_min = 0.960, T_max = 0.992
15848 measured reflections
4153 independent reflections
3090 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.119
S = 1.03
4153 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2ⁱ	0.88	2.14	2.906 (2)	146
N4—H4N⋯O2ⁱⁱ	0.88	2.04	2.906 (2)	166
N1—H1⋯O1ⁱⁱⁱ	0.88	2.01	2.8331 (19)	154
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z; (iii) -x+2, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2012 $[Oxford Diffraction (2012). Oxford Diffraction Ltd, Yarnton,England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2012 $[Oxford Diffraction (2012). Oxford Diffraction Ltd, Yarnton,England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019181/tk5236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019181/tk5236Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019181/tk5236Isup3.cml

checkCIF report

Comment top

Quinoxaline derivatives have been discovered as leads for a novel series of dipeptidyl peptidase-IV molecules (Cheon et al., 2004). They are also used as ligands for the strychnine-insensitive glycine site (Jackson et al., 1991) and as new fluorescent probes for amyloid-β fibrils (Benzeid et al., 2012).

The crystal structure of title compound is build up from two fused six-membered rings (N1, N2 C1–C8) linked to a benzohydrazide system (N3, N4, O1, C9–C15) and a dimethylformamide solvent molecule as shown in Fig. 1. The fused rings system is almost planar with the maximum deviation from the mean plane being -0.024 (2) Å for the C1 atom. The dihedral angle between the terminal phenyl ring and the fused ring system is 70.05 (8)°. In the crystal structure, the molecules and the solvent are linked by N—H···O hydrogen bond to form a layer parallel to (0 1 0), Table 1.

Related literature top

For potential applications of quinoxaline derivatives, see: Cheon et al. (2004); Jackson et al. (1991); Benzeid et al. (2012).

Experimental top

A mixture of quinoxaline-2,3-dithione (1 g, 5.15 10 ^-3 mol), benzhydrazide (1.4 g, 0.01 mol) and DMF (40 ml) was boiled under reflux for 48 h. The volume of DMF was reduced under reduced pressure (2 ml) and the residue was taken up into 100 ml of diethyl ether. An oily product precipitated quickly after addition of diethyl ether. After centrifugation the diethyl ether phase was recovered and the precipitate (oily product) was washed with diethyl ether (2 x 3 ml). The product crystallized in the diethyl ether phase overnight at room temperature. Crystals were collected, washed with diethyl ether (5 ml) and dried under vacuum. Yield: 700 mg, 46%.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2012); cell refinement: CrysAlis RED (Oxford Diffraction, 2012); data reduction: CrysAlis RED (Oxford Diffraction, 2012); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structures of the components of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

N'-(3-Sulfanylidene-3,4-dihydroquinoxalin-2-yl)benzohydrazide dimethylformamide monosolvate top

Crystal data top

C₁₅H₁₂N₄OS·C₃H₇NO	F(000) = 776
M_r = 369.44	D_x = 1.375 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4153 reflections
a = 10.4053 (2) Å	θ = 3.1–27.9°
b = 16.8563 (5) Å	µ = 0.21 mm⁻¹
c = 10.3624 (2) Å	T = 180 K
β = 100.882 (2)°	Plate, yellow
V = 1784.83 (7) Å³	0.20 × 0.12 × 0.04 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	4153 independent reflections
Graphite monochromator	3090 reflections with I > 2σ(I)
Detector resolution: 16.1978 pixels mm^-1	R_int = 0.043
ω scans	θ_max = 27.9°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2012)	h = −13→13
T_min = 0.960, T_max = 0.992	k = −21→21
15848 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0514P)² + 0.657P] where P = (F_o² + 2F_c²)/3
4153 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₂N₄OS·C₃H₇NO	V = 1784.83 (7) Å³
M_r = 369.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4053 (2) Å	µ = 0.21 mm⁻¹
b = 16.8563 (5) Å	T = 180 K
c = 10.3624 (2) Å	0.20 × 0.12 × 0.04 mm
β = 100.882 (2)°

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	4153 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2012)	3090 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.992	R_int = 0.043
15848 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
4153 reflections	Δρ_min = −0.25 e Å⁻³
235 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.90077 (17)	0.07517 (11)	0.52315 (18)	0.0238 (4)
C2	0.97172 (18)	0.13196 (12)	0.33400 (19)	0.0277 (4)
C3	1.0611 (2)	0.18006 (13)	0.2856 (2)	0.0353 (5)
H3	1.1320	0.2040	0.3438	0.042*
C4	1.0448 (2)	0.19226 (15)	0.1524 (2)	0.0451 (6)
H4	1.1046	0.2249	0.1179	0.054*
C5	0.9401 (2)	0.15666 (16)	0.0673 (2)	0.0475 (6)
H5	0.9300	0.1649	−0.0248	0.057*
C6	0.8519 (2)	0.11001 (15)	0.1155 (2)	0.0403 (5)
H6	0.7808	0.0868	0.0565	0.048*
C7	0.86557 (18)	0.09631 (12)	0.25101 (19)	0.0289 (4)
C8	0.79327 (17)	0.03925 (11)	0.42633 (17)	0.0231 (4)
C9	0.64594 (16)	−0.12910 (12)	0.37671 (17)	0.0245 (4)
C10	0.53941 (17)	−0.17643 (11)	0.29440 (17)	0.0230 (4)
C11	0.40700 (17)	−0.15997 (12)	0.28901 (18)	0.0264 (4)
H11	0.3817	−0.1175	0.3391	0.032*
C12	0.31276 (19)	−0.20563 (13)	0.2106 (2)	0.0339 (5)
H12	0.2226	−0.1951	0.2083	0.041*
C13	0.3494 (2)	−0.26669 (13)	0.1356 (2)	0.0357 (5)
H13	0.2843	−0.2962	0.0787	0.043*
C14	0.4802 (2)	−0.28490 (12)	0.14304 (19)	0.0332 (5)
H14	0.5049	−0.3278	0.0934	0.040*
C15	0.57487 (19)	−0.24034 (12)	0.22322 (18)	0.0290 (4)
H15	0.6647	−0.2534	0.2298	0.035*
C16	0.5145 (2)	−0.09973 (14)	−0.0642 (2)	0.0382 (5)
H16A	0.4905	−0.0777	0.0155	0.057*
H16C	0.5032	−0.1575	−0.0649	0.057*
H16B	0.4582	−0.0768	−0.1418	0.057*
C17	0.7469 (2)	−0.09952 (17)	0.0508 (2)	0.0474 (6)
H17A	0.8339	−0.0827	0.0381	0.071*
H17B	0.7472	−0.1568	0.0666	0.071*
H17C	0.7246	−0.0716	0.1265	0.071*
C18	0.6865 (2)	−0.05175 (12)	−0.17353 (19)	0.0314 (4)
H18	0.7771	−0.0417	−0.1684	0.038*
N1	0.98526 (15)	0.11775 (9)	0.46798 (15)	0.0263 (4)
H1	1.0539	0.1380	0.5203	0.032*
N2	0.77741 (15)	0.04876 (10)	0.29977 (15)	0.0277 (4)
N3	0.70812 (15)	−0.00590 (10)	0.47938 (15)	0.0306 (4)
H3N	0.7111	−0.0052	0.5648	0.037*
N4	0.61647 (15)	−0.05320 (10)	0.39948 (15)	0.0264 (4)
H4N	0.5395	−0.0336	0.3639	0.032*
N5	0.65059 (16)	−0.08079 (10)	−0.06642 (15)	0.0312 (4)
O1	0.75344 (13)	−0.15906 (9)	0.42053 (14)	0.0373 (4)
O2	0.61339 (14)	−0.03660 (9)	−0.27891 (13)	0.0342 (3)
S1	0.91904 (5)	0.06336 (3)	0.68523 (5)	0.03039 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0196 (8)	0.0200 (9)	0.0310 (10)	0.0026 (7)	0.0027 (7)	−0.0020 (7)
C2	0.0236 (9)	0.0272 (10)	0.0317 (10)	0.0012 (8)	0.0033 (8)	0.0048 (8)
C3	0.0263 (10)	0.0356 (12)	0.0422 (12)	−0.0059 (9)	0.0017 (9)	0.0084 (9)
C4	0.0325 (11)	0.0529 (15)	0.0495 (13)	−0.0053 (10)	0.0066 (10)	0.0223 (11)
C5	0.0351 (12)	0.0684 (18)	0.0373 (12)	−0.0015 (12)	0.0028 (10)	0.0218 (12)
C6	0.0291 (11)	0.0580 (15)	0.0308 (11)	−0.0051 (10)	−0.0018 (9)	0.0078 (10)
C7	0.0219 (9)	0.0338 (11)	0.0306 (10)	−0.0001 (8)	0.0037 (8)	0.0043 (8)
C8	0.0192 (8)	0.0234 (10)	0.0256 (9)	0.0012 (7)	0.0016 (7)	−0.0026 (7)
C9	0.0180 (8)	0.0364 (11)	0.0193 (9)	−0.0036 (8)	0.0043 (7)	0.0022 (8)
C10	0.0222 (8)	0.0265 (10)	0.0197 (8)	−0.0018 (7)	0.0020 (7)	0.0027 (7)
C11	0.0229 (9)	0.0269 (10)	0.0290 (10)	−0.0018 (8)	0.0040 (8)	−0.0027 (8)
C12	0.0233 (9)	0.0340 (12)	0.0411 (11)	−0.0028 (8)	−0.0020 (8)	−0.0018 (9)
C13	0.0369 (11)	0.0318 (12)	0.0340 (11)	−0.0097 (9)	−0.0041 (9)	−0.0025 (9)
C14	0.0454 (12)	0.0270 (11)	0.0274 (10)	0.0004 (9)	0.0072 (9)	−0.0033 (8)
C15	0.0275 (9)	0.0335 (11)	0.0262 (9)	0.0027 (8)	0.0060 (8)	0.0025 (8)
C16	0.0374 (11)	0.0440 (13)	0.0349 (11)	−0.0037 (10)	0.0114 (9)	0.0034 (10)
C17	0.0407 (13)	0.0691 (17)	0.0308 (11)	0.0010 (12)	0.0030 (10)	0.0126 (11)
C18	0.0308 (10)	0.0328 (11)	0.0312 (10)	−0.0021 (9)	0.0075 (8)	0.0017 (8)
N1	0.0198 (7)	0.0260 (9)	0.0312 (9)	−0.0047 (6)	0.0006 (6)	−0.0010 (7)
N2	0.0214 (8)	0.0350 (10)	0.0260 (8)	−0.0024 (7)	0.0025 (6)	−0.0003 (7)
N3	0.0284 (8)	0.0413 (10)	0.0213 (8)	−0.0152 (7)	0.0031 (7)	−0.0067 (7)
N4	0.0199 (7)	0.0328 (9)	0.0246 (8)	−0.0067 (7)	−0.0008 (6)	−0.0023 (7)
N5	0.0300 (9)	0.0392 (10)	0.0241 (8)	0.0000 (7)	0.0048 (7)	0.0041 (7)
O1	0.0192 (7)	0.0457 (9)	0.0432 (8)	0.0007 (6)	−0.0041 (6)	−0.0027 (7)
O2	0.0356 (8)	0.0374 (8)	0.0286 (7)	−0.0017 (6)	0.0033 (6)	0.0069 (6)
S1	0.0267 (2)	0.0378 (3)	0.0253 (3)	−0.0027 (2)	0.00135 (19)	−0.0026 (2)

Geometric parameters (Å, º) top

C1—N1	1.343 (2)	C11—H11	0.9500
C1—C8	1.483 (2)	C12—C13	1.386 (3)
C1—S1	1.6661 (19)	C12—H12	0.9500
C2—N1	1.390 (2)	C13—C14	1.383 (3)
C2—C3	1.396 (3)	C13—H13	0.9500
C2—C7	1.401 (3)	C14—C15	1.384 (3)
C3—C4	1.374 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.401 (3)	C16—N5	1.456 (3)
C4—H4	0.9500	C16—H16A	0.9800
C5—C6	1.372 (3)	C16—H16C	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—C7	1.404 (3)	C17—N5	1.456 (3)
C6—H6	0.9500	C17—H17A	0.9800
C7—N2	1.384 (2)	C17—H17B	0.9800
C8—N2	1.300 (2)	C17—H17C	0.9800
C8—N3	1.360 (2)	C18—O2	1.234 (2)
C9—O1	1.233 (2)	C18—N5	1.330 (3)
C9—N4	1.347 (3)	C18—H18	0.9500
C9—C10	1.495 (2)	N1—H1	0.8800
C10—C15	1.394 (3)	N3—N4	1.390 (2)
C10—C11	1.396 (2)	N3—H3N	0.8800
C11—C12	1.383 (3)	N4—H4N	0.8800

N1—C1—C8	113.62 (16)	C14—C13—H13	119.8
N1—C1—S1	122.24 (13)	C12—C13—H13	119.8
C8—C1—S1	124.13 (14)	C13—C14—C15	119.64 (19)
N1—C2—C3	120.68 (17)	C13—C14—H14	120.2
N1—C2—C7	117.32 (17)	C15—C14—H14	120.2
C3—C2—C7	122.00 (18)	C14—C15—C10	120.48 (18)
C4—C3—C2	118.92 (19)	C14—C15—H15	119.8
C4—C3—H3	120.5	C10—C15—H15	119.8
C2—C3—H3	120.5	N5—C16—H16A	109.5
C3—C4—C5	120.2 (2)	N5—C16—H16C	109.5
C3—C4—H4	119.9	H16A—C16—H16C	109.5
C5—C4—H4	119.9	N5—C16—H16B	109.5
C6—C5—C4	120.7 (2)	H16A—C16—H16B	109.5
C6—C5—H5	119.7	H16C—C16—H16B	109.5
C4—C5—H5	119.7	N5—C17—H17A	109.5
C5—C6—C7	120.7 (2)	N5—C17—H17B	109.5
C5—C6—H6	119.7	H17A—C17—H17B	109.5
C7—C6—H6	119.7	N5—C17—H17C	109.5
N2—C7—C2	121.65 (17)	H17A—C17—H17C	109.5
N2—C7—C6	120.77 (17)	H17B—C17—H17C	109.5
C2—C7—C6	117.58 (18)	O2—C18—N5	126.27 (19)
N2—C8—N3	120.54 (16)	O2—C18—H18	116.9
N2—C8—C1	124.59 (17)	N5—C18—H18	116.9
N3—C8—C1	114.87 (16)	C1—N1—C2	124.49 (15)
O1—C9—N4	123.04 (17)	C1—N1—H1	117.8
O1—C9—C10	120.98 (18)	C2—N1—H1	117.8
N4—C9—C10	115.98 (15)	C8—N2—C7	118.23 (16)
C15—C10—C11	119.35 (17)	C8—N3—N4	120.40 (15)
C15—C10—C9	118.19 (16)	C8—N3—H3N	119.8
C11—C10—C9	122.44 (17)	N4—N3—H3N	119.8
C12—C11—C10	119.86 (18)	C9—N4—N3	119.73 (15)
C12—C11—H11	120.1	C9—N4—H4N	120.1
C10—C11—H11	120.1	N3—N4—H4N	120.1
C11—C12—C13	120.21 (19)	C18—N5—C17	121.23 (17)
C11—C12—H12	119.9	C18—N5—C16	121.41 (17)
C13—C12—H12	119.9	C17—N5—C16	117.25 (17)
C14—C13—C12	120.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.88	2.14	2.906 (2)	146
N4—H4N···O2ⁱⁱ	0.88	2.04	2.906 (2)	166
N1—H1···O1ⁱⁱⁱ	0.88	2.01	2.8331 (19)	154

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z; (iii) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.88	2.14	2.906 (2)	146
N4—H4N···O2ⁱⁱ	0.88	2.04	2.906 (2)	166
N1—H1···O1ⁱⁱⁱ	0.88	2.01	2.8331 (19)	154

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y, −z; (iii) −x+2, −y, −z+1.

References

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Volume 69| Part 8| August 2013| Page o1268

doi:10.1107/S1600536813019181

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(3-Sulfanyl­­idene-3,4-di­hydro­quinoxalin-2-yl)benzohydrazide di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N′-(3-Sulfanylidene-3,4-dihydroquinoxalin-2-yl)benzohydrazide dimethylformamide monosolvate