Crystal structure of 1-(4-formyl-benzyl-idene)-4-methyl-thio-semicarbazone.

The structure of the title compound, C10H11N3OS, comprises an approximately planar mol-ecule, with the r.m.s. deviation for the 15 non-H atoms being 0.089 Å. The conformation about the imine bond is E and an intra-molecular N-H⋯N hydrogen bond is evident. Mol-ecules are linked into a supra-molecular chain along the b axis by N-H⋯S hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Jagst et al. (2005 ▶). For biological properties, see: Serda et al. (2012 ▶). For supra­molecular studies of thio­semicarbazones, see: Alonso et al. (2002 ▶).

Experimental

Crystal data

C10H11N3OS

M = 221.28

Orthorhombic,

a = 13.1231 (3) Å

b = 8.8559 (2) Å

c = 19.3702 (4) Å

V = 2251.14 (9) Å3

Z = 8

Cu Kα radiation

μ = 2.38 mm−1

T = 296 K

0.14 × 0.13 × 0.05 mm

Data collection

Bruker CCD SMART 6000 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.730, T max = 0.898

22698 measured reflections

1986 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.100

S = 1.08

1986 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814016407/tk5328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016407/tk5328Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016407/tk5328Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016407/tk5328fig1.tif

The mol­ecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814016407/tk5328fig2.tif

View of supra­molecular chain formed by N—H⋯S inter­actions (dashed lines).

CCDC reference: 1014062

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H11N3OS	F(000) = 928
Mr = 221.28	Dx = 1.306 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9894 reflections
a = 13.1231 (3) Å	θ = 4.6–66.6°
b = 8.8559 (2) Å	µ = 2.38 mm−1
c = 19.3702 (4) Å	T = 296 K
V = 2251.14 (9) Å3	Plate, yellow
Z = 8	0.14 × 0.13 × 0.05 mm

Bruker CCD SMART 6000 diffractometer	1986 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 66.6°, θmin = 4.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→15
Tmin = 0.730, Tmax = 0.898	k = −10→10
22698 measured reflections	l = −22→22

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.3598P] where P = (Fo2 + 2Fc2)/3
1986 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.16 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	0.90393 (3)	1.04683 (4)	0.40705 (2)	0.06222 (18)
O1	0.88220 (12)	−0.01792 (18)	0.72752 (8)	0.0921 (5)
N1	0.81376 (12)	0.78044 (16)	0.39148 (7)	0.0655 (4)
C1	0.87314 (11)	0.86850 (16)	0.42864 (8)	0.0517 (3)
N2	0.90945 (10)	0.81086 (15)	0.48868 (7)	0.0579 (3)
C2	0.92328 (12)	0.62083 (19)	0.56504 (9)	0.0605 (4)
H2	0.9617	0.6879	0.5913	0.073*
N3	0.88781 (9)	0.66473 (14)	0.50704 (7)	0.0542 (3)
C3	0.90556 (11)	0.46928 (19)	0.59137 (8)	0.0536 (4)
C4	0.93836 (15)	0.43343 (19)	0.65777 (9)	0.0678 (4)
H4	0.9707	0.5066	0.6844	0.081*
C5	0.92354 (14)	0.2913 (2)	0.68448 (9)	0.0675 (4)
H5	0.9454	0.2692	0.7290	0.081*
C6	0.87602 (11)	0.18070 (18)	0.64526 (8)	0.0554 (4)
C7	0.84324 (11)	0.21631 (18)	0.57902 (8)	0.0558 (4)
H7	0.8112	0.1429	0.5524	0.067*
C8	0.85745 (11)	0.35836 (17)	0.55224 (8)	0.0543 (4)
H8	0.8349	0.3805	0.5079	0.065*
C9	0.86069 (14)	0.0265 (2)	0.67155 (10)	0.0678 (4)
H9	0.8313	−0.0428	0.6415	0.081*
C10	0.76953 (19)	0.8229 (2)	0.32581 (10)	0.0924 (7)
H10A	0.7165	0.8957	0.3332	0.139*
H10B	0.7415	0.7351	0.3038	0.139*
H10C	0.8213	0.8660	0.2968	0.139*
H2N	0.9542 (15)	0.865 (2)	0.5138 (9)	0.075 (5)*
H1	0.8010 (15)	0.695 (2)	0.4085 (9)	0.073 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0655 (3)	0.0429 (3)	0.0782 (3)	−0.00218 (15)	−0.01004 (18)	0.00628 (16)
O1	0.1022 (10)	0.0890 (10)	0.0851 (9)	0.0013 (8)	−0.0037 (8)	0.0320 (8)
N1	0.0797 (9)	0.0507 (8)	0.0662 (8)	−0.0120 (7)	−0.0135 (7)	0.0075 (6)
C1	0.0458 (7)	0.0469 (8)	0.0622 (8)	0.0028 (6)	0.0023 (6)	0.0008 (6)
N2	0.0550 (7)	0.0479 (7)	0.0707 (8)	−0.0065 (5)	−0.0097 (6)	0.0089 (6)
C2	0.0566 (8)	0.0555 (9)	0.0693 (9)	−0.0066 (7)	−0.0097 (7)	0.0047 (7)
N3	0.0477 (6)	0.0487 (7)	0.0663 (8)	−0.0014 (5)	−0.0001 (5)	0.0069 (6)
C3	0.0468 (8)	0.0555 (10)	0.0585 (9)	0.0000 (6)	−0.0032 (6)	0.0047 (6)
C4	0.0759 (11)	0.0641 (10)	0.0635 (9)	−0.0119 (8)	−0.0176 (8)	0.0023 (7)
C5	0.0763 (10)	0.0707 (11)	0.0555 (9)	−0.0044 (8)	−0.0131 (8)	0.0106 (8)
C6	0.0504 (8)	0.0573 (9)	0.0585 (8)	0.0032 (6)	0.0018 (6)	0.0059 (7)
C7	0.0539 (8)	0.0544 (9)	0.0590 (8)	−0.0013 (6)	−0.0037 (6)	−0.0017 (7)
C8	0.0536 (8)	0.0564 (9)	0.0531 (7)	0.0013 (6)	−0.0071 (6)	0.0040 (6)
C9	0.0656 (10)	0.0653 (10)	0.0724 (10)	0.0035 (8)	0.0001 (8)	0.0122 (8)
C10	0.1231 (18)	0.0784 (12)	0.0756 (11)	−0.0277 (12)	−0.0324 (12)	0.0131 (10)

S1—C1	1.6829 (15)	C3—C8	1.392 (2)
O1—C9	1.187 (2)	C3—C4	1.393 (2)
N1—C1	1.317 (2)	C4—C5	1.375 (2)
N1—C10	1.448 (2)	C5—C6	1.388 (2)
C1—N2	1.356 (2)	C6—C7	1.390 (2)
N2—N3	1.3718 (18)	C6—C9	1.471 (2)
C2—N3	1.277 (2)	C7—C8	1.373 (2)
C2—C3	1.454 (2)
C1—N1—C10	124.33 (15)	C4—C3—C2	118.99 (15)
N1—C1—N2	116.98 (14)	C5—C4—C3	120.82 (15)
N1—C1—S1	124.20 (12)	C4—C5—C6	120.26 (15)
N2—C1—S1	118.81 (12)	C5—C6—C7	118.98 (15)
C1—N2—N3	120.30 (13)	C5—C6—C9	121.80 (15)
N3—C2—C3	122.09 (15)	C7—C6—C9	119.21 (15)
C2—N3—N2	116.10 (13)	C8—C7—C6	120.97 (15)
C8—C3—C4	118.82 (15)	C7—C8—C3	120.15 (14)
C8—C3—C2	122.19 (14)	O1—C9—C6	126.24 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···S1i	0.902 (19)	2.53 (2)	3.4154 (14)	165.6 (16)
N1—H1···N3	0.84 (2)	2.238 (18)	2.6467 (18)	109.9 (15)
N1—H1···S1ii	0.84 (2)	2.992 (19)	3.5401 (15)	124.6 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯S1i	0.902 (19)	2.53 (2)	3.4154 (14)	165.6 (16)
N1—H1⋯N3	0.84 (2)	2.238 (18)	2.6467 (18)	109.9 (15)
N1—H1⋯S1ii	0.84 (2)	2.992 (19)	3.5401 (15)	124.6 (16)

Symmetry codes: (i) ; (ii) .