(E)-4-(Benz-yloxy)benzaldehyde thio-semicarbazone.

In the title compound, C(15)H(15)N(3)OS, the thio-semicarbazone group adopts an E configuration with respect to the C=N bond. The benzaldehyde thio-semicarbazone fragment is almost planar [maximum deviation = 0.012 (1) Å], while the dihedral angle between the benz-yloxy and phenyl rings is 72.48 (5)°. In the crystal structure, mol-ecules are inter-connected by N-H⋯N and N-H⋯S hydrogen bonds, forming a two-dimensional network parallel to the bc plane and are further stacked along the a axis by π-π inter-actions [centroid-centroid separation 3.9043 (7) Å]. The crystal structure is also stabilized by C-H⋯π inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures of thio­semicarbazones, see, for example: John et al. (2003 ▶); Joseph et al. (2004 ▶). For applications and bioactivities of thio­semicarbazones, see, for example: Al-Awadi et al. (2008 ▶); Amoedo et al. (2006 ▶); Chandra et al., (2001 ▶); Demertzi et al. (2007 ▶); Kizilcikli et al. (2004 ▶); Mirsha et al. (2006 ▶); Offiong & Martelli (1997 ▶); Sing et al. (2001 ▶).

Experimental

Crystal data

C15H15N3OS

M = 285.37

Monoclinic,

a = 11.0269 (1) Å

b = 12.6668 (2) Å

c = 10.8774 (1) Å

β = 116.099 (1)°

V = 1364.39 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100.0 (1) K

0.42 × 0.31 × 0.23 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.792, T max = 0.947

20710 measured reflections

3983 independent reflections

3517 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.03

3983 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 ; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012671/sj2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012671/sj2492Isup2.hkl

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

C15H15N3OS	F000 = 600
Mr = 285.37	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Melting point: 446 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 11.0269 (1) Å	Cell parameters from 3983 reflections
b = 12.6668 (2) Å	θ = 2.1–30.0º
c = 10.8774 (1) Å	µ = 0.24 mm−1
β = 116.099 (1)º	T = 100.0 (1) K
V = 1364.39 (3) Å3	Block, colorless
Z = 4	0.42 × 0.31 × 0.23 mm

Bruker SMART APEX2 CCD area-detector diffractometer	3983 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.1º
ω scans	h = −15→14
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −17→17
Tmin = 0.792, Tmax = 0.947	l = −15→14
20710 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.4873P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3983 reflections	Δρmax = 0.48 e Å−3
193 parameters	Δρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	−0.13297 (3)	0.13427 (2)	0.97645 (3)	0.01819 (8)
O1	0.32553 (8)	0.07638 (6)	0.33345 (8)	0.01820 (17)
N1	0.04289 (10)	0.10009 (8)	0.73443 (9)	0.01734 (18)
N2	0.00675 (10)	0.08433 (8)	0.83961 (9)	0.01797 (19)
N3	−0.13647 (10)	0.22436 (8)	0.75438 (10)	0.01930 (19)
C1	0.44624 (11)	0.26954 (9)	0.20175 (11)	0.0185 (2)
H1A	0.4399	0.3177	0.2632	0.022*
C2	0.53207 (12)	0.29079 (9)	0.14214 (11)	0.0190 (2)
H2A	0.5835	0.3522	0.1645	0.023*
C3	0.54055 (12)	0.21970 (9)	0.04895 (11)	0.0196 (2)
H3A	0.5973	0.2334	0.0081	0.024*
C4	0.46359 (13)	0.12808 (9)	0.01727 (12)	0.0214 (2)
H4A	0.4685	0.0808	−0.0458	0.026*
C5	0.37939 (12)	0.10629 (9)	0.07858 (11)	0.0206 (2)
H5A	0.3295	0.0441	0.0577	0.025*
C6	0.36955 (11)	0.17766 (9)	0.17140 (11)	0.0174 (2)
C7	0.27374 (12)	0.16007 (10)	0.23367 (11)	0.0203 (2)
H7A	0.2647	0.2244	0.2774	0.024*
H7B	0.1853	0.1410	0.1630	0.024*
C8	0.26799 (11)	0.06651 (8)	0.42162 (10)	0.0158 (2)
C9	0.32639 (11)	−0.00843 (9)	0.52540 (11)	0.0178 (2)
H9A	0.3968	−0.0507	0.5288	0.021*
C10	0.27868 (12)	−0.01940 (9)	0.62342 (11)	0.0177 (2)
H10A	0.3173	−0.0696	0.6922	0.021*
C11	0.17333 (11)	0.04386 (8)	0.62022 (10)	0.0160 (2)
C12	0.11361 (11)	0.11615 (9)	0.51313 (11)	0.0168 (2)
H12A	0.0419	0.1574	0.5084	0.020*
C13	0.15942 (11)	0.12737 (9)	0.41392 (11)	0.0170 (2)
H13A	0.1181	0.1752	0.3426	0.020*
C14	0.12869 (11)	0.03475 (9)	0.72786 (11)	0.0175 (2)
H14A	0.1629	−0.0190	0.7923	0.021*
C15	−0.08583 (11)	0.14858 (8)	0.84847 (11)	0.0156 (2)
H1N2	0.0392 (16)	0.0301 (13)	0.8951 (16)	0.025 (4)*
H1N3	−0.1132 (17)	0.2256 (13)	0.6853 (18)	0.031 (4)*
H2N3	−0.1995 (18)	0.2624 (14)	0.7562 (17)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.02249 (15)	0.01892 (14)	0.01894 (14)	0.00132 (10)	0.01441 (11)	0.00114 (9)
O1	0.0202 (4)	0.0215 (4)	0.0181 (3)	0.0037 (3)	0.0132 (3)	0.0039 (3)
N1	0.0192 (5)	0.0209 (4)	0.0157 (4)	−0.0012 (3)	0.0111 (4)	0.0006 (3)
N2	0.0217 (5)	0.0200 (4)	0.0176 (4)	0.0032 (4)	0.0136 (4)	0.0035 (3)
N3	0.0189 (5)	0.0224 (5)	0.0197 (4)	0.0039 (4)	0.0114 (4)	0.0045 (4)
C1	0.0198 (5)	0.0211 (5)	0.0152 (4)	0.0028 (4)	0.0082 (4)	0.0004 (4)
C2	0.0184 (5)	0.0208 (5)	0.0170 (5)	−0.0012 (4)	0.0070 (4)	0.0012 (4)
C3	0.0204 (5)	0.0239 (5)	0.0176 (5)	0.0023 (4)	0.0112 (4)	0.0042 (4)
C4	0.0292 (6)	0.0210 (5)	0.0186 (5)	0.0021 (4)	0.0147 (5)	0.0004 (4)
C5	0.0253 (6)	0.0196 (5)	0.0191 (5)	−0.0028 (4)	0.0118 (4)	0.0004 (4)
C6	0.0167 (5)	0.0224 (5)	0.0144 (4)	0.0029 (4)	0.0079 (4)	0.0038 (4)
C7	0.0182 (5)	0.0272 (6)	0.0185 (5)	0.0041 (4)	0.0107 (4)	0.0064 (4)
C8	0.0163 (5)	0.0182 (5)	0.0155 (4)	−0.0017 (4)	0.0095 (4)	−0.0013 (4)
C9	0.0194 (5)	0.0174 (5)	0.0202 (5)	0.0021 (4)	0.0121 (4)	0.0007 (4)
C10	0.0205 (5)	0.0170 (5)	0.0185 (5)	0.0014 (4)	0.0111 (4)	0.0021 (4)
C11	0.0177 (5)	0.0170 (5)	0.0158 (4)	−0.0014 (4)	0.0097 (4)	−0.0011 (4)
C12	0.0151 (5)	0.0206 (5)	0.0163 (5)	0.0010 (4)	0.0083 (4)	0.0001 (4)
C13	0.0157 (5)	0.0210 (5)	0.0152 (4)	0.0017 (4)	0.0077 (4)	0.0021 (4)
C14	0.0200 (5)	0.0181 (5)	0.0171 (4)	−0.0004 (4)	0.0106 (4)	0.0011 (4)
C15	0.0146 (5)	0.0173 (5)	0.0160 (4)	−0.0024 (4)	0.0078 (4)	−0.0010 (4)

S1—C15	1.6964 (11)	C4—H4A	0.9300
O1—C8	1.3688 (12)	C5—C6	1.3946 (15)
O1—C7	1.4430 (13)	C5—H5A	0.9300
N1—C14	1.2826 (14)	C6—C7	1.5014 (15)
N1—N2	1.3815 (12)	C7—H7A	0.9700
N2—C15	1.3417 (14)	C7—H7B	0.9700
N2—H1N2	0.880 (17)	C8—C13	1.3950 (15)
N3—C15	1.3335 (14)	C8—C9	1.3966 (15)
N3—H1N3	0.894 (17)	C9—C10	1.3879 (14)
N3—H2N3	0.853 (18)	C9—H9A	0.9300
C1—C2	1.3886 (15)	C10—C11	1.3990 (15)
C1—C6	1.3903 (16)	C10—H10A	0.9300
C1—H1A	0.9300	C11—C12	1.3979 (15)
C2—C3	1.3894 (15)	C11—C14	1.4606 (14)
C2—H2A	0.9300	C12—C13	1.3856 (14)
C3—C4	1.3887 (16)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.3884 (16)	C14—H14A	0.9300
C8—O1—C7	116.23 (8)	C6—C7—H7A	109.9
C14—N1—N2	116.20 (9)	O1—C7—H7B	109.9
C15—N2—N1	118.53 (9)	C6—C7—H7B	109.9
C15—N2—H1N2	121.1 (10)	H7A—C7—H7B	108.3
N1—N2—H1N2	120.2 (10)	O1—C8—C13	123.89 (9)
C15—N3—H1N3	118.6 (11)	O1—C8—C9	115.94 (9)
C15—N3—H2N3	117.4 (11)	C13—C8—C9	120.16 (9)
H1N3—N3—H2N3	123.1 (15)	C10—C9—C8	119.55 (10)
C2—C1—C6	121.31 (10)	C10—C9—H9A	120.2
C2—C1—H1A	119.3	C8—C9—H9A	120.2
C6—C1—H1A	119.3	C9—C10—C11	120.98 (10)
C1—C2—C3	119.57 (11)	C9—C10—H10A	119.5
C1—C2—H2A	120.2	C11—C10—H10A	119.5
C3—C2—H2A	120.2	C12—C11—C10	118.52 (9)
C4—C3—C2	119.52 (10)	C12—C11—C14	121.22 (10)
C4—C3—H3A	120.2	C10—C11—C14	120.25 (10)
C2—C3—H3A	120.2	C13—C12—C11	121.11 (10)
C5—C4—C3	120.78 (10)	C13—C12—H12A	119.4
C5—C4—H4A	119.6	C11—C12—H12A	119.4
C3—C4—H4A	119.6	C12—C13—C8	119.60 (10)
C4—C5—C6	120.02 (11)	C12—C13—H13A	120.2
C4—C5—H5A	120.0	C8—C13—H13A	120.2
C6—C5—H5A	120.0	N1—C14—C11	120.71 (10)
C1—C6—C5	118.79 (10)	N1—C14—H14A	119.6
C1—C6—C7	119.49 (10)	C11—C14—H14A	119.6
C5—C6—C7	121.65 (10)	N3—C15—N2	117.16 (9)
O1—C7—C6	108.91 (9)	N3—C15—S1	122.05 (8)
O1—C7—H7A	109.9	N2—C15—S1	120.78 (8)
C14—N1—N2—C15	−177.98 (10)	C13—C8—C9—C10	−2.17 (16)
C6—C1—C2—C3	0.83 (17)	C8—C9—C10—C11	−0.31 (17)
C1—C2—C3—C4	−0.35 (17)	C9—C10—C11—C12	2.21 (16)
C2—C3—C4—C5	−0.62 (18)	C9—C10—C11—C14	−177.07 (10)
C3—C4—C5—C6	1.13 (18)	C10—C11—C12—C13	−1.66 (16)
C2—C1—C6—C5	−0.32 (16)	C14—C11—C12—C13	177.61 (10)
C2—C1—C6—C7	−177.44 (10)	C11—C12—C13—C8	−0.77 (17)
C4—C5—C6—C1	−0.65 (17)	O1—C8—C13—C12	−175.94 (10)
C4—C5—C6—C7	176.40 (11)	C9—C8—C13—C12	2.71 (16)
C8—O1—C7—C6	165.49 (9)	N2—N1—C14—C11	179.67 (9)
C1—C6—C7—O1	−109.78 (11)	C12—C11—C14—N1	−7.05 (17)
C5—C6—C7—O1	73.19 (13)	C10—C11—C14—N1	172.21 (10)
C7—O1—C8—C13	4.11 (15)	N1—N2—C15—N3	−0.34 (15)
C7—O1—C8—C9	−174.59 (10)	N1—N2—C15—S1	−179.21 (8)
O1—C8—C9—C10	176.58 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.880 (16)	2.467 (16)	3.3403 (10)	171.9 (14)
N3—H1N3···N1	0.895 (19)	2.229 (18)	2.6104 (16)	105.2 (13)
N3—H1N3···S1ii	0.895 (19)	2.815 (17)	3.5285 (11)	137.7 (14)
C10—H10A···Cg1iii	0.93	2.97	3.8325 (13)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.880 (16)	2.467 (16)	3.3403 (10)	171.9 (14)
N3—H1N3⋯N1	0.895 (19)	2.229 (18)	2.6104 (16)	105.2 (13)
N3—H1N3⋯S1ii	0.895 (19)	2.815 (17)	3.5285 (11)	137.7 (14)
C10—H10A⋯Cg1iii	0.93	2.97	3.8325 (13)	154

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the the C1–C6 ring.