(E)-1-(3-Cyano-benzyl-idene)thio-semi-carbazide N,N-dimethyl-formamide solvate.

The title compound, C(9)H(8)N(4)S·C(3)H(7)NO, adopts an E configuration about both the C=N and C-N bonds. Inter-molecular N-H⋯O hydrogen bonding links the compound to the DMF solvent molecule. The crystal packing is characterized by chains of mol-ecules linked by inter-molecular N-H⋯S hydrogen-bonding inter-actions.

Related literature

For the biological activity of thio­semicarbazones, see: Lovejoy & Richardson et al. (2002 ▶). For a related structure, see: Wu et al. (2009 ▶). For comparitive geometrical parameters, see: Sutton et al. (1965 ▶).

Experimental

Crystal data

C9H8N4S·n class="Chemical">C3H7NO

M = 277.35

Monoclinic,

a = 7.312 (7) Å

b = 8.945 (3) Å

c = 22.316 (19) Å

β = 92.12 (2)°

V = 1458.6 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.742, T max = 1.000

9561 measured reflections

3280 independent reflections

2065 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.109

S = 1.01

3280 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000214X/pv2253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000214X/pv2253Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H8N4S·C3H7NO	F(000) = 584
Mr = 277.35	Dx = 1.263 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2851 reflections
a = 7.312 (7) Å	θ = 2.3–27.4°
b = 8.945 (3) Å	µ = 0.22 mm−1
c = 22.316 (19) Å	T = 293 K
β = 92.12 (2)°	Block, pale yellow
V = 1458.6 (19) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 2.5°
CCD_Profile_fitting scans	h = −7→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.742, Tmax = 1.000	l = −28→24
9561 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.020P)2 + 0.850P] where P = (Fo2 + 2Fc2)/3
3280 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.60691 (11)	0.46135 (8)	0.74146 (3)	0.0636 (2)
N2	0.7389 (2)	0.40996 (19)	0.57477 (8)	0.0425 (4)
N3	0.6727 (2)	0.4707 (2)	0.62652 (8)	0.0451 (5)
H3A	0.6198	0.5566	0.6258	0.054*
C6	0.8765 (3)	0.2925 (2)	0.46844 (10)	0.0430 (5)
H6A	0.8857	0.2327	0.5025	0.052*
N4	0.7782 (3)	0.2634 (2)	0.67556 (9)	0.0585 (6)
H4A	0.8181	0.2320	0.6420	0.070*
H4B	0.7939	0.2102	0.7074	0.070*
C8	0.7256 (3)	0.4903 (2)	0.52748 (10)	0.0428 (5)
H8A	0.6724	0.5846	0.5288	0.051*
C9	0.6924 (3)	0.3936 (2)	0.67810 (10)	0.0441 (5)
C7	1.0229 (3)	0.0938 (3)	0.41270 (10)	0.0518 (6)
C1	0.7947 (3)	0.4329 (2)	0.47102 (9)	0.0402 (5)
N1	1.0774 (3)	−0.0249 (3)	0.41178 (10)	0.0714 (7)
C5	0.9444 (3)	0.2423 (2)	0.41459 (10)	0.0444 (5)
C2	0.7832 (3)	0.5198 (3)	0.41938 (10)	0.0501 (6)
H2B	0.7295	0.6140	0.4207	0.060*
C3	0.8504 (3)	0.4685 (3)	0.36610 (10)	0.0565 (6)
H3B	0.8407	0.5281	0.3320	0.068*
C4	0.9316 (3)	0.3298 (3)	0.36311 (10)	0.0535 (6)
H4C	0.9770	0.2953	0.3273	0.064*
N5	0.4289 (3)	0.9814 (2)	0.63750 (9)	0.0565 (5)
C10	0.4945 (4)	0.8452 (3)	0.64567 (13)	0.0641 (7)
H10A	0.4904	0.8055	0.6841	0.077*
O1	0.5606 (3)	0.76602 (19)	0.60695 (9)	0.0718 (6)
C11	0.4348 (4)	1.0502 (3)	0.57878 (13)	0.0756 (8)
H11A	0.4869	0.9813	0.5512	0.113*
H11B	0.5085	1.1389	0.5813	0.113*
H11C	0.3129	1.0759	0.5650	0.113*
C12	0.3501 (4)	1.0680 (4)	0.68517 (15)	0.0925 (11)
H12A	0.3521	1.0099	0.7214	0.139*
H12B	0.2261	1.0936	0.6740	0.139*
H12C	0.4202	1.1577	0.6917	0.139*

	U11	U22	U33	U12	U13	U23
S1	0.0917 (5)	0.0516 (4)	0.0489 (4)	−0.0029 (4)	0.0207 (3)	−0.0114 (3)
N2	0.0512 (12)	0.0372 (9)	0.0396 (10)	0.0037 (8)	0.0069 (9)	−0.0025 (8)
N3	0.0550 (12)	0.0366 (9)	0.0444 (11)	0.0082 (9)	0.0102 (9)	−0.0053 (8)
C6	0.0502 (14)	0.0383 (12)	0.0403 (12)	0.0002 (10)	0.0011 (10)	0.0022 (9)
N4	0.0848 (16)	0.0461 (11)	0.0454 (12)	0.0152 (11)	0.0121 (11)	0.0056 (9)
C8	0.0450 (13)	0.0359 (12)	0.0477 (14)	0.0064 (10)	0.0030 (10)	−0.0018 (10)
C9	0.0508 (15)	0.0351 (11)	0.0465 (13)	−0.0047 (10)	0.0054 (11)	−0.0038 (10)
C7	0.0604 (16)	0.0490 (14)	0.0468 (14)	0.0050 (12)	0.0114 (12)	−0.0048 (11)
C1	0.0421 (13)	0.0373 (12)	0.0413 (12)	0.0011 (9)	0.0014 (10)	−0.0015 (9)
N1	0.0898 (18)	0.0539 (14)	0.0718 (16)	0.0190 (13)	0.0214 (13)	−0.0032 (12)
C5	0.0486 (14)	0.0392 (12)	0.0454 (13)	0.0005 (10)	0.0031 (11)	−0.0050 (10)
C2	0.0603 (16)	0.0407 (12)	0.0492 (14)	0.0063 (11)	−0.0003 (12)	0.0025 (11)
C3	0.0730 (18)	0.0554 (15)	0.0408 (14)	0.0039 (13)	0.0006 (12)	0.0081 (12)
C4	0.0642 (17)	0.0558 (15)	0.0411 (14)	−0.0010 (13)	0.0075 (12)	−0.0042 (11)
N5	0.0650 (14)	0.0431 (11)	0.0621 (14)	0.0022 (10)	0.0117 (11)	−0.0079 (10)
C10	0.074 (2)	0.0515 (16)	0.0665 (18)	−0.0059 (14)	0.0011 (15)	0.0052 (13)
O1	0.0870 (15)	0.0432 (10)	0.0860 (14)	0.0116 (10)	0.0131 (11)	−0.0066 (10)
C11	0.088 (2)	0.0541 (17)	0.086 (2)	0.0066 (15)	0.0132 (17)	0.0126 (15)
C12	0.095 (2)	0.083 (2)	0.102 (3)	−0.0076 (19)	0.034 (2)	−0.0443 (19)

S1—C9	1.680 (2)	C2—C3	1.382 (3)
N2—C8	1.277 (3)	C2—H2B	0.9300
N2—N3	1.380 (2)	C3—C4	1.378 (3)
N3—C9	1.345 (3)	C3—H3B	0.9300
N3—H3A	0.8600	C4—H4C	0.9300
C6—C5	1.392 (3)	N5—C10	1.320 (3)
C6—C1	1.393 (3)	N5—C11	1.450 (3)
C6—H6A	0.9300	N5—C12	1.452 (3)
N4—C9	1.325 (3)	C10—O1	1.230 (3)
N4—H4A	0.8600	C10—H10A	0.9300
N4—H4B	0.8600	C11—H11A	0.9600
C8—C1	1.467 (3)	C11—H11B	0.9600
C8—H8A	0.9300	C11—H11C	0.9600
C7—N1	1.135 (3)	C12—H12A	0.9600
C7—C5	1.447 (3)	C12—H12B	0.9600
C1—C2	1.390 (3)	C12—H12C	0.9600
C5—C4	1.390 (3)
C8—N2—N3	116.85 (18)	C1—C2—H2B	119.5
C9—N3—N2	118.97 (18)	C4—C3—C2	120.5 (2)
C9—N3—H3A	120.5	C4—C3—H3B	119.7
N2—N3—H3A	120.5	C2—C3—H3B	119.7
C5—C6—C1	119.6 (2)	C3—C4—C5	118.9 (2)
C5—C6—H6A	120.2	C3—C4—H4C	120.6
C1—C6—H6A	120.2	C5—C4—H4C	120.6
C9—N4—H4A	120.0	C10—N5—C11	119.6 (2)
C9—N4—H4B	120.0	C10—N5—C12	122.9 (3)
H4A—N4—H4B	120.0	C11—N5—C12	117.5 (2)
N2—C8—C1	119.7 (2)	O1—C10—N5	125.8 (3)
N2—C8—H8A	120.2	O1—C10—H10A	117.1
C1—C8—H8A	120.2	N5—C10—H10A	117.1
N4—C9—N3	116.8 (2)	N5—C11—H11A	109.5
N4—C9—S1	123.00 (18)	N5—C11—H11B	109.5
N3—C9—S1	120.24 (17)	H11A—C11—H11B	109.5
N1—C7—C5	177.1 (3)	N5—C11—H11C	109.5
C2—C1—C6	118.9 (2)	H11A—C11—H11C	109.5
C2—C1—C8	120.3 (2)	H11B—C11—H11C	109.5
C6—C1—C8	120.8 (2)	N5—C12—H12A	109.5
C4—C5—C6	121.1 (2)	N5—C12—H12B	109.5
C4—C5—C7	120.5 (2)	H12A—C12—H12B	109.5
C6—C5—C7	118.4 (2)	N5—C12—H12C	109.5
C3—C2—C1	121.0 (2)	H12A—C12—H12C	109.5
C3—C2—H2B	119.5	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	1.96	2.795 (3)	162
N4—H4A···N2	0.86	2.25	2.610 (3)	105
N4—H4A···N1i	0.86	2.35	3.101 (3)	146
N4—H4B···S1ii	0.86	2.59	3.364 (2)	150
C8—H8A···O1	0.93	2.54	3.293 (3)	138
C11—H11A···O1	0.96	2.34	2.767 (3)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	1.96	2.795 (3)	162
N4—H4A⋯N1i	0.86	2.35	3.101 (3)	146
N4—H4B⋯S1ii	0.86	2.59	3.364 (2)	150
C8—H8A⋯O1	0.93	2.54	3.293 (3)	138

Symmetry codes: (i) ; (ii) .