(Z)-2-[(E)-2-(1-Benzothio-phen-3-yl-methyl-idene)hydrazin-1-yl-idene]-1,2-diphenyl-ethanone.

The title compound, C(23)H(16)N(2)OS, is not planar, the phenyl ring of the benzoyl group making a dihedral of 77.61 (7)° with the benzothio-phene system ring. The benzothio-phene system and the remaining phenyl ring make an angle of 12.71 (13)°. The conformation around the imine functions is E for the C=N bond towards the benzothio-phene system and Z for the C=N bond towards the benzoyl group. The packing of the mol-ecules shows C-H⋯π inter-actions. A weak intramolecular C-H⋯N bond also occurs.

Related literature

For general background to benzothio­phenes, see: Katritzky et al. (1996 ▶); Shishoo & Jain (1992 ▶). For the biological properties of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶). For industrial applications of Shiff bases, see: Taggi et al. (2002 ▶). For related structures, see: Dege et al. (2006 ▶, 2007 ▶); Demirtaş et al. (2009 ▶); Gül et al. (2007 ▶). For structural properties of benzothio­phene derivatives, see: Inamoto et al. (2008 ▶); Mlochowski & Potaczek (2009 ▶); Novopoltseva (1995 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H16N2OS

M = 368.44

Monoclinic,

a = 17.1009 (7) Å

b = 8.7700 (4) Å

c = 13.1170 (6) Å

β = 103.898 (4)°

V = 1909.63 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.30 × 0.15 × 0.10 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.843, T max = 1.000

7369 measured reflections

3815 independent reflections

2566 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.121

S = 1.07

3815 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S1600536812030978/vm2179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030978/vm2179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030978/vm2179Isup3.cml

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

C23H16N2OS	F(000) = 768
Mr = 368.44	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2365 reflections
a = 17.1009 (7) Å	θ = 3.2–27.5°
b = 8.7700 (4) Å	µ = 0.18 mm−1
c = 13.1170 (6) Å	T = 293 K
β = 103.898 (4)°	Plate, yellow
V = 1909.63 (15) Å3	0.30 × 0.15 × 0.10 mm
Z = 4

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	3815 independent reflections
Radiation source: fine-focus sealed tube	2566 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0454 pixels mm-1	θmax = 27.6°, θmin = 3.2°
ω scans	h = −22→21
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −10→6
Tmin = 0.843, Tmax = 1.000	l = −15→16
7369 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0328P)2 + 0.4842P] where P = (Fo2 + 2Fc2)/3
3815 reflections	(Δ/σ)max = 0.002
244 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.63404 (17)	0.2840 (3)	0.5699 (2)	0.0696 (8)
H1	0.6819	0.2657	0.5501	0.083*
C2	0.5635 (2)	0.2214 (4)	0.5132 (3)	0.0925 (10)
H2	0.5638	0.1615	0.4548	0.111*
C3	0.4926 (2)	0.2463 (5)	0.5417 (3)	0.1115 (13)
H3	0.4451	0.2028	0.5030	0.134*
C4	0.49182 (19)	0.3354 (5)	0.6271 (3)	0.1178 (14)
H4	0.4437	0.3526	0.6465	0.141*
C5	0.56261 (17)	0.4000 (4)	0.6846 (3)	0.0901 (10)
H5	0.5618	0.4610	0.7423	0.108*
C6	0.63441 (15)	0.3744 (3)	0.6568 (2)	0.0588 (7)
C7	0.71001 (14)	0.4422 (3)	0.71807 (18)	0.0516 (6)
C8	0.71003 (13)	0.5224 (3)	0.82084 (19)	0.0522 (6)
C9	0.70993 (13)	0.6910 (3)	0.82297 (19)	0.0507 (6)
C10	0.69128 (16)	0.7746 (3)	0.7316 (2)	0.0640 (7)
H10	0.6795	0.7249	0.6671	0.077*
C11	0.68997 (18)	0.9321 (3)	0.7350 (3)	0.0817 (9)
H11	0.6760	0.9881	0.6731	0.098*
C12	0.70923 (18)	1.0052 (4)	0.8298 (3)	0.0875 (10)
H12	0.7079	1.1112	0.8322	0.105*
C13	0.73038 (17)	0.9241 (4)	0.9211 (3)	0.0811 (9)
H13	0.7454	0.9747	0.9851	0.097*
C14	0.72938 (15)	0.7666 (3)	0.9182 (2)	0.0657 (7)
H14	0.7418	0.7113	0.9805	0.079*
C15	0.90807 (14)	0.4568 (3)	0.73987 (18)	0.0508 (6)
H15	0.9073	0.3914	0.6838	0.061*
C16	0.98486 (13)	0.5071 (2)	0.80241 (17)	0.0453 (5)
C17	1.05487 (14)	0.4515 (3)	0.78494 (18)	0.0541 (6)
H17	1.0562	0.3823	0.7316	0.065*
C18	1.08272 (13)	0.6305 (3)	0.93254 (17)	0.0460 (6)
C19	1.00005 (13)	0.6127 (2)	0.88917 (16)	0.0413 (5)
C20	0.94578 (15)	0.6956 (3)	0.93244 (17)	0.0506 (6)
H20	0.8905	0.6849	0.9060	0.061*
C21	0.97565 (17)	0.7928 (3)	1.01439 (19)	0.0620 (7)
H21	0.9401	0.8490	1.0430	0.074*
C22	1.05794 (19)	0.8089 (3)	1.0555 (2)	0.0688 (8)
H22	1.0764	0.8758	1.1111	0.083*
C23	1.11240 (17)	0.7285 (3)	1.01580 (19)	0.0601 (7)
H23	1.1675	0.7391	1.0437	0.072*
N1	0.77520 (12)	0.4280 (2)	0.68712 (15)	0.0569 (5)
N2	0.84100 (12)	0.4976 (2)	0.75772 (15)	0.0533 (5)
O1	0.70894 (11)	0.4453 (2)	0.89756 (14)	0.0710 (5)
S1	1.13984 (4)	0.51911 (8)	0.86872 (5)	0.0595 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0639 (18)	0.0671 (18)	0.0739 (18)	−0.0102 (15)	0.0091 (15)	−0.0083 (15)
C2	0.077 (2)	0.096 (2)	0.093 (2)	−0.015 (2)	−0.0014 (19)	−0.024 (2)
C3	0.063 (2)	0.132 (3)	0.122 (3)	−0.022 (2)	−0.013 (2)	−0.023 (3)
C4	0.0462 (19)	0.166 (4)	0.135 (3)	−0.015 (2)	0.011 (2)	−0.035 (3)
C5	0.0543 (18)	0.113 (3)	0.101 (2)	−0.0033 (18)	0.0145 (17)	−0.023 (2)
C6	0.0498 (15)	0.0572 (16)	0.0660 (16)	−0.0034 (13)	0.0075 (13)	0.0031 (14)
C7	0.0488 (14)	0.0463 (14)	0.0569 (15)	0.0009 (12)	0.0073 (12)	0.0034 (12)
C8	0.0380 (13)	0.0612 (16)	0.0553 (15)	0.0007 (12)	0.0070 (11)	0.0053 (13)
C9	0.0399 (13)	0.0557 (15)	0.0561 (14)	0.0034 (12)	0.0104 (11)	0.0000 (13)
C10	0.0716 (18)	0.0583 (17)	0.0625 (16)	−0.0013 (15)	0.0166 (14)	0.0042 (14)
C11	0.083 (2)	0.064 (2)	0.097 (2)	0.0007 (17)	0.0186 (18)	0.0164 (18)
C12	0.074 (2)	0.0573 (19)	0.127 (3)	−0.0005 (17)	0.015 (2)	−0.008 (2)
C13	0.069 (2)	0.075 (2)	0.092 (2)	0.0066 (17)	0.0054 (17)	−0.0267 (19)
C14	0.0563 (16)	0.075 (2)	0.0629 (17)	0.0112 (15)	0.0092 (13)	−0.0056 (15)
C15	0.0536 (15)	0.0504 (14)	0.0488 (13)	−0.0037 (12)	0.0131 (11)	−0.0048 (11)
C16	0.0461 (13)	0.0443 (13)	0.0479 (13)	−0.0011 (11)	0.0160 (11)	0.0011 (11)
C17	0.0550 (15)	0.0565 (15)	0.0537 (14)	−0.0022 (13)	0.0186 (12)	−0.0079 (12)
C18	0.0497 (14)	0.0420 (13)	0.0460 (13)	−0.0021 (11)	0.0109 (11)	0.0067 (11)
C19	0.0481 (13)	0.0365 (12)	0.0411 (12)	−0.0003 (11)	0.0143 (10)	0.0061 (10)
C20	0.0559 (15)	0.0472 (14)	0.0503 (14)	0.0045 (12)	0.0160 (12)	0.0057 (12)
C21	0.078 (2)	0.0545 (16)	0.0563 (16)	0.0100 (15)	0.0221 (14)	−0.0039 (13)
C22	0.091 (2)	0.0583 (17)	0.0535 (16)	−0.0025 (17)	0.0094 (15)	−0.0092 (13)
C23	0.0635 (17)	0.0570 (16)	0.0543 (15)	−0.0085 (14)	0.0034 (13)	0.0044 (13)
N1	0.0458 (12)	0.0620 (13)	0.0592 (13)	−0.0024 (11)	0.0055 (10)	−0.0073 (11)
N2	0.0465 (11)	0.0583 (13)	0.0533 (12)	−0.0032 (11)	0.0085 (9)	−0.0067 (10)
O1	0.0777 (13)	0.0735 (12)	0.0623 (11)	0.0000 (10)	0.0175 (10)	0.0162 (10)
S1	0.0460 (4)	0.0669 (5)	0.0675 (4)	0.0005 (3)	0.0172 (3)	−0.0010 (3)

C1—C2	1.371 (4)	C12—H12	0.9300
C1—C6	1.387 (3)	C13—C14	1.381 (4)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.369 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—N2	1.276 (3)
C3—C4	1.369 (4)	C15—C16	1.440 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.384 (4)	C16—C17	1.362 (3)
C4—H4	0.9300	C16—C19	1.442 (3)
C5—C6	1.380 (4)	C17—S1	1.704 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.474 (3)	C18—C23	1.386 (3)
C7—N1	1.281 (3)	C18—C19	1.400 (3)
C7—C8	1.521 (3)	C18—S1	1.733 (2)
C8—O1	1.217 (3)	C19—C20	1.402 (3)
C8—C9	1.479 (3)	C20—C21	1.371 (3)
C9—C10	1.376 (3)	C20—H20	0.9300
C9—C14	1.383 (3)	C21—C22	1.388 (4)
C10—C11	1.382 (4)	C21—H21	0.9300
C10—H10	0.9300	C22—C23	1.367 (4)
C11—C12	1.367 (4)	C22—H22	0.9300
C11—H11	0.9300	C23—H23	0.9300
C12—C13	1.364 (4)	N1—N2	1.413 (3)
C2—C1—C6	120.3 (3)	C12—C13—C14	119.9 (3)
C2—C1—H1	119.8	C12—C13—H13	120.0
C6—C1—H1	119.8	C14—C13—H13	120.0
C3—C2—C1	120.6 (3)	C13—C14—C9	120.2 (3)
C3—C2—H2	119.7	C13—C14—H14	119.9
C1—C2—H2	119.7	C9—C14—H14	119.9
C2—C3—C4	119.9 (3)	N2—C15—C16	123.1 (2)
C2—C3—H3	120.1	N2—C15—H15	118.4
C4—C3—H3	120.1	C16—C15—H15	118.4
C3—C4—C5	120.0 (3)	C17—C16—C15	120.8 (2)
C3—C4—H4	120.0	C17—C16—C19	111.3 (2)
C5—C4—H4	120.0	C15—C16—C19	127.8 (2)
C6—C5—C4	120.4 (3)	C16—C17—S1	114.51 (18)
C6—C5—H5	119.8	C16—C17—H17	122.7
C4—C5—H5	119.8	S1—C17—H17	122.7
C5—C6—C1	118.7 (3)	C23—C18—C19	122.2 (2)
C5—C6—C7	120.7 (3)	C23—C18—S1	126.00 (19)
C1—C6—C7	120.6 (2)	C19—C18—S1	111.85 (17)
N1—C7—C6	120.3 (2)	C18—C19—C20	118.7 (2)
N1—C7—C8	120.7 (2)	C18—C19—C16	111.42 (19)
C6—C7—C8	118.9 (2)	C20—C19—C16	129.9 (2)
O1—C8—C9	122.7 (2)	C21—C20—C19	118.8 (2)
O1—C8—C7	118.6 (2)	C21—C20—H20	120.6
C9—C8—C7	118.7 (2)	C19—C20—H20	120.6
C10—C9—C14	119.2 (2)	C20—C21—C22	121.3 (2)
C10—C9—C8	121.2 (2)	C20—C21—H21	119.3
C14—C9—C8	119.7 (2)	C22—C21—H21	119.3
C9—C10—C11	120.4 (3)	C23—C22—C21	121.3 (2)
C9—C10—H10	119.8	C23—C22—H22	119.4
C11—C10—H10	119.8	C21—C22—H22	119.4
C12—C11—C10	119.8 (3)	C22—C23—C18	117.8 (2)
C12—C11—H11	120.1	C22—C23—H23	121.1
C10—C11—H11	120.1	C18—C23—H23	121.1
C13—C12—C11	120.5 (3)	C7—N1—N2	111.53 (19)
C13—C12—H12	119.7	C15—N2—N1	111.59 (19)
C11—C12—H12	119.7	C17—S1—C18	90.89 (11)
C6—C1—C2—C3	−0.4 (5)	C8—C9—C14—C13	179.3 (2)
C1—C2—C3—C4	0.5 (6)	N2—C15—C16—C17	175.2 (2)
C2—C3—C4—C5	−0.1 (6)	N2—C15—C16—C19	−3.0 (4)
C3—C4—C5—C6	−0.4 (6)	C15—C16—C17—S1	−178.11 (17)
C4—C5—C6—C1	0.5 (5)	C19—C16—C17—S1	0.3 (3)
C4—C5—C6—C7	−179.7 (3)	C23—C18—C19—C20	−0.7 (3)
C2—C1—C6—C5	−0.1 (4)	S1—C18—C19—C20	180.00 (15)
C2—C1—C6—C7	−179.9 (3)	C23—C18—C19—C16	178.8 (2)
C5—C6—C7—N1	−174.5 (3)	S1—C18—C19—C16	−0.4 (2)
C1—C6—C7—N1	5.3 (4)	C17—C16—C19—C18	0.1 (3)
C5—C6—C7—C8	8.4 (4)	C15—C16—C19—C18	178.4 (2)
C1—C6—C7—C8	−171.8 (2)	C17—C16—C19—C20	179.6 (2)
N1—C7—C8—O1	−101.5 (3)	C15—C16—C19—C20	−2.1 (4)
C6—C7—C8—O1	75.6 (3)	C18—C19—C20—C21	1.0 (3)
N1—C7—C8—C9	79.5 (3)	C16—C19—C20—C21	−178.4 (2)
C6—C7—C8—C9	−103.3 (3)	C19—C20—C21—C22	−0.7 (4)
O1—C8—C9—C10	−163.7 (2)	C20—C21—C22—C23	0.0 (4)
C7—C8—C9—C10	15.1 (3)	C21—C22—C23—C18	0.4 (4)
O1—C8—C9—C14	16.7 (3)	C19—C18—C23—C22	0.0 (3)
C7—C8—C9—C14	−164.4 (2)	S1—C18—C23—C22	179.19 (19)
C14—C9—C10—C11	−1.7 (4)	C6—C7—N1—N2	−178.57 (19)
C8—C9—C10—C11	178.8 (2)	C8—C7—N1—N2	−1.5 (3)
C9—C10—C11—C12	1.6 (4)	C16—C15—N2—N1	−178.0 (2)
C10—C11—C12—C13	0.5 (5)	C7—N1—N2—C15	166.1 (2)
C11—C12—C13—C14	−2.5 (5)	C16—C17—S1—C18	−0.51 (19)
C12—C13—C14—C9	2.4 (4)	C23—C18—S1—C17	−178.7 (2)
C10—C9—C14—C13	−0.3 (4)	C19—C18—S1—C17	0.54 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···N2	0.93	2.53	3.083 (3)	118
C4—H4···Cg3i	0.93	2.74	3.648 (4)	167
C15—H15···Cg4ii	0.93	3.00	3.879 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C9–C14 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯N2	0.93	2.53	3.083 (3)	118
C4—H4⋯Cg3i	0.93	2.74	3.648 (4)	167
C15—H15⋯Cg4ii	0.93	3.00	3.879 (3)	158

Symmetry codes: (i) ; (ii) .