(E)-4-Octyloxybenzaldehyde thio-semicarbazone.

In the title compound, C(16)H(25)N(3)OS, the thio-semicarbazone group adopts an E configuration with respect to the C=N bond and is almost coplanar with the benzene ring, forming a dihedral angle of 9.3 (1)°. In the crystal packing, the mol-ecules lie along the a axis in an anti-parallel arrangement and are held in place by van der Waals inter-actions. As a consequence, there is relatively low anisotropic thermal motion in the terminal atoms of the n-octyl chain.

Related literature

For the related structures, see: Basuli et al. (2000 ▶); Narayana et al. (2007 ▶); Pal et al. (2002 ▶); Tian et al. (2002 ▶); Tarafder et al. (2008 ▶).

Experimental

Crystal data

C16H25N3OS

M = 307.45

Triclinic,

a = 5.785 (2) Å

b = 7.586 (2) Å

c = 20.789 (4) Å

α = 94.74 (2)°

β = 91.85 (2)°

γ = 104.42 (3)°

V = 879.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.42 × 0.40 × 0.14 mm

Data collection

Enraf–Nonius dip1030 image-plate diffractometer

9930 measured reflections

3226 independent reflections

2749 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.140

S = 1.04

3226 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: XPRESS (MacScience, 2002 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054841/fj2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054841/fj2264Isup2.hkl

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

C16H25N3OS	Z = 2
Mr = 307.45	F(000) = 332
Triclinic, P1	Dx = 1.161 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.785 (2) Å	Cell parameters from 146 reflections
b = 7.586 (2) Å	θ = 3.0–18.1°
c = 20.789 (4) Å	µ = 0.19 mm−1
α = 94.74 (2)°	T = 293 K
β = 91.85 (2)°	Plate, colorless
γ = 104.42 (3)°	0.42 × 0.40 × 0.14 mm
V = 879.2 (4) Å3

Enraf–Nonius dip1030 image-plate diffractometer	2749 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.7°, θmin = 3.6°
φ–scans with narrow frames	h = −7→7
9930 measured reflections	k = −9→8
3226 independent reflections	l = −25→25

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) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1026P)2 + 0.0242P] where P = (Fo2 + 2Fc2)/3
3226 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	1.33919 (6)	−0.29398 (5)	0.99374 (2)	0.06930 (19)
N1	1.0386 (2)	0.02579 (17)	0.89975 (6)	0.0648 (3)
N2	1.1983 (2)	−0.04336 (17)	0.93483 (6)	0.0690 (3)
H2	1.3435	0.0203	0.9421	0.083*
N3	0.9025 (2)	−0.29670 (17)	0.94909 (6)	0.0668 (3)
H3A	0.8033	−0.2489	0.9295	0.080*
H3B	0.8534	−0.4024	0.9631	0.080*
O1	0.6110 (2)	0.55328 (16)	0.73145 (6)	0.0812 (3)
C1	1.1305 (2)	−0.20768 (19)	0.95761 (7)	0.0591 (3)
C2	1.1216 (3)	0.1882 (2)	0.88465 (7)	0.0663 (4)
H2A	1.2764	0.2498	0.8995	0.080*
C3	0.9864 (3)	0.2818 (2)	0.84546 (7)	0.0630 (4)
C4	0.7501 (3)	0.2031 (2)	0.82202 (7)	0.0681 (4)
H4	0.6725	0.0867	0.8321	0.082*
C5	0.6322 (3)	0.2971 (2)	0.78409 (8)	0.0716 (4)
H5	0.4761	0.2431	0.7683	0.086*
C6	0.7444 (3)	0.4721 (2)	0.76919 (7)	0.0677 (4)
C7	0.9777 (3)	0.5528 (2)	0.79263 (7)	0.0726 (4)
H7	1.0536	0.6704	0.7833	0.087*
C8	1.0957 (3)	0.4563 (2)	0.82997 (7)	0.0698 (4)
H8	1.2526	0.5100	0.8451	0.084*
C9	0.7089 (4)	0.7404 (2)	0.72041 (9)	0.0880 (5)
H9A	0.8564	0.7529	0.6983	0.106*
H9B	0.7432	0.8161	0.7612	0.106*
C10	0.5257 (4)	0.7986 (3)	0.67937 (9)	0.0890 (5)
H10A	0.3717	0.7624	0.6982	0.107*
H10B	0.5693	0.9309	0.6805	0.107*
C11	0.5012 (4)	0.7192 (3)	0.60985 (8)	0.0811 (5)
H11A	0.4523	0.5869	0.6085	0.097*
H11B	0.6561	0.7522	0.5913	0.097*
C12	0.3221 (3)	0.7838 (3)	0.56889 (9)	0.0817 (5)
H12A	0.1660	0.7448	0.5863	0.098*
H12B	0.3662	0.9164	0.5727	0.098*
C13	0.3025 (3)	0.7155 (2)	0.49799 (9)	0.0826 (5)
H13A	0.2573	0.5828	0.4940	0.099*
H13B	0.4583	0.7543	0.4803	0.099*
C14	0.1228 (3)	0.7824 (3)	0.45814 (8)	0.0810 (5)
H14A	−0.0331	0.7420	0.4756	0.097*
H14B	0.1667	0.9150	0.4629	0.097*
C15	0.1029 (4)	0.7182 (3)	0.38689 (9)	0.0891 (5)
H15A	0.0562	0.5857	0.3819	0.107*
H15B	0.2589	0.7573	0.3693	0.107*
C16	−0.0752 (4)	0.7893 (3)	0.34816 (10)	0.0987 (6)
H16A	−0.2329	0.7416	0.3624	0.148*
H16B	−0.0710	0.7509	0.3031	0.148*
H16C	−0.0347	0.9204	0.3544	0.148*

	U11	U22	U33	U12	U13	U23
S1	0.0526 (3)	0.0696 (3)	0.0871 (3)	0.01517 (17)	−0.00582 (18)	0.02038 (19)
N1	0.0600 (7)	0.0703 (8)	0.0671 (7)	0.0211 (5)	−0.0045 (5)	0.0120 (6)
N2	0.0551 (7)	0.0706 (8)	0.0817 (8)	0.0141 (6)	−0.0097 (6)	0.0204 (6)
N3	0.0527 (6)	0.0681 (7)	0.0810 (8)	0.0158 (5)	−0.0032 (5)	0.0155 (6)
O1	0.0863 (8)	0.0834 (7)	0.0823 (7)	0.0315 (6)	−0.0029 (6)	0.0277 (6)
C1	0.0534 (7)	0.0639 (8)	0.0604 (8)	0.0158 (6)	0.0003 (6)	0.0060 (6)
C2	0.0666 (9)	0.0705 (9)	0.0627 (8)	0.0181 (7)	−0.0032 (6)	0.0120 (7)
C3	0.0680 (8)	0.0687 (8)	0.0555 (7)	0.0224 (6)	0.0007 (6)	0.0090 (6)
C4	0.0709 (9)	0.0664 (8)	0.0691 (9)	0.0191 (7)	0.0004 (7)	0.0152 (7)
C5	0.0677 (9)	0.0792 (10)	0.0713 (9)	0.0228 (7)	−0.0027 (7)	0.0159 (7)
C6	0.0774 (9)	0.0744 (9)	0.0587 (8)	0.0309 (7)	0.0027 (7)	0.0132 (7)
C7	0.0831 (10)	0.0666 (9)	0.0687 (9)	0.0177 (7)	0.0007 (7)	0.0153 (7)
C8	0.0712 (9)	0.0711 (9)	0.0662 (9)	0.0159 (7)	−0.0042 (7)	0.0102 (7)
C9	0.1125 (15)	0.0781 (11)	0.0813 (11)	0.0368 (10)	−0.0047 (10)	0.0185 (9)
C10	0.1121 (15)	0.0853 (11)	0.0837 (12)	0.0468 (11)	0.0025 (10)	0.0239 (9)
C11	0.0900 (12)	0.0816 (11)	0.0815 (11)	0.0349 (9)	0.0066 (9)	0.0225 (8)
C12	0.0882 (12)	0.0861 (11)	0.0802 (11)	0.0350 (9)	0.0053 (9)	0.0224 (9)
C13	0.0886 (12)	0.0810 (11)	0.0843 (11)	0.0299 (9)	0.0039 (9)	0.0174 (9)
C14	0.0875 (12)	0.0802 (10)	0.0797 (11)	0.0276 (9)	0.0040 (8)	0.0146 (8)
C15	0.0945 (13)	0.0900 (12)	0.0859 (12)	0.0307 (10)	−0.0021 (9)	0.0068 (9)
C16	0.1001 (14)	0.1156 (15)	0.0842 (12)	0.0372 (12)	−0.0079 (10)	0.0060 (11)

S1—C1	1.6930 (15)	C9—H9A	0.9700
N1—C2	1.275 (2)	C9—H9B	0.9700
N1—N2	1.3863 (16)	C10—C11	1.507 (3)
N2—C1	1.341 (2)	C10—H10A	0.9700
N2—H2	0.8600	C10—H10B	0.9700
N3—C1	1.3227 (19)	C11—C12	1.518 (2)
N3—H3A	0.8600	C11—H11A	0.9700
N3—H3B	0.8600	C11—H11B	0.9700
O1—C6	1.3665 (19)	C12—C13	1.513 (3)
O1—C9	1.432 (2)	C12—H12A	0.9700
C2—C3	1.453 (2)	C12—H12B	0.9700
C2—H2A	0.9300	C13—C14	1.517 (2)
C3—C8	1.387 (2)	C13—H13A	0.9700
C3—C4	1.402 (2)	C13—H13B	0.9700
C4—C5	1.377 (2)	C14—C15	1.512 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.390 (2)	C14—H14B	0.9700
C5—H5	0.9300	C15—C16	1.515 (3)
C6—C7	1.389 (2)	C15—H15A	0.9700
C7—C8	1.383 (2)	C15—H15B	0.9700
C7—H7	0.9300	C16—H16A	0.9600
C8—H8	0.9300	C16—H16B	0.9600
C9—C10	1.511 (3)	C16—H16C	0.9600
C2—N1—N2	114.83 (13)	C9—C10—H10A	108.7
C1—N2—N1	121.23 (12)	C11—C10—H10B	108.7
C1—N2—H2	119.4	C9—C10—H10B	108.7
N1—N2—H2	119.4	H10A—C10—H10B	107.6
C1—N3—H3A	120.0	C10—C11—C12	113.38 (15)
C1—N3—H3B	120.0	C10—C11—H11A	108.9
H3A—N3—H3B	120.0	C12—C11—H11A	108.9
C6—O1—C9	117.89 (14)	C10—C11—H11B	108.9
N3—C1—N2	117.74 (13)	C12—C11—H11B	108.9
N3—C1—S1	123.14 (12)	H11A—C11—H11B	107.7
N2—C1—S1	119.09 (11)	C13—C12—C11	114.97 (15)
N1—C2—C3	123.26 (14)	C13—C12—H12A	108.5
N1—C2—H2A	118.4	C11—C12—H12A	108.5
C3—C2—H2A	118.4	C13—C12—H12B	108.5
C8—C3—C4	118.26 (14)	C11—C12—H12B	108.5
C8—C3—C2	118.79 (14)	H12A—C12—H12B	107.5
C4—C3—C2	122.94 (15)	C12—C13—C14	113.91 (15)
C5—C4—C3	120.37 (15)	C12—C13—H13A	108.8
C5—C4—H4	119.8	C14—C13—H13A	108.8
C3—C4—H4	119.8	C12—C13—H13B	108.8
C4—C5—C6	120.57 (15)	C14—C13—H13B	108.8
C4—C5—H5	119.7	H13A—C13—H13B	107.7
C6—C5—H5	119.7	C15—C14—C13	114.88 (16)
O1—C6—C7	124.47 (15)	C15—C14—H14A	108.5
O1—C6—C5	115.77 (15)	C13—C14—H14A	108.5
C7—C6—C5	119.76 (15)	C15—C14—H14B	108.5
C8—C7—C6	119.26 (15)	C13—C14—H14B	108.5
C8—C7—H7	120.4	H14A—C14—H14B	107.5
C6—C7—H7	120.4	C14—C15—C16	113.71 (16)
C7—C8—C3	121.78 (15)	C14—C15—H15A	108.8
C7—C8—H8	119.1	C16—C15—H15A	108.8
C3—C8—H8	119.1	C14—C15—H15B	108.8
O1—C9—C10	107.53 (17)	C16—C15—H15B	108.8
O1—C9—H9A	110.2	H15A—C15—H15B	107.7
C10—C9—H9A	110.2	C15—C16—H16A	109.5
O1—C9—H9B	110.2	C15—C16—H16B	109.5
C10—C9—H9B	110.2	H16A—C16—H16B	109.5
H9A—C9—H9B	108.5	C15—C16—H16C	109.5
C11—C10—C9	114.12 (15)	H16A—C16—H16C	109.5
C11—C10—H10A	108.7	H16B—C16—H16C	109.5
C2—N1—N2—C1	175.56 (13)	O1—C6—C7—C8	−179.39 (14)
N1—N2—C1—N3	−4.3 (2)	C5—C6—C7—C8	0.7 (2)
N1—N2—C1—S1	174.08 (10)	C6—C7—C8—C3	−0.9 (2)
N2—N1—C2—C3	177.06 (12)	C4—C3—C8—C7	0.2 (2)
N1—C2—C3—C8	−177.92 (14)	C2—C3—C8—C7	179.72 (13)
N1—C2—C3—C4	1.6 (2)	C6—O1—C9—C10	−178.39 (13)
C8—C3—C4—C5	0.7 (2)	O1—C9—C10—C11	−73.0 (2)
C2—C3—C4—C5	−178.83 (13)	C9—C10—C11—C12	−178.21 (16)
C3—C4—C5—C6	−0.8 (2)	C10—C11—C12—C13	176.73 (17)
C9—O1—C6—C7	−6.4 (2)	C11—C12—C13—C14	−179.85 (15)
C9—O1—C6—C5	173.52 (14)	C12—C13—C14—C15	179.08 (16)
C4—C5—C6—O1	−179.76 (13)	C13—C14—C15—C16	−179.20 (17)
C4—C5—C6—C7	0.1 (2)