N,N'-Bis[(E)-2-thienylmethyl-ene]-4,4'-oxydianiline.

In the title mol-ecule, C(22)H(16)N(2)OS(2), which demonstrates non-crystallographic C(2) pseudosymmetry [C-O-C angle = 121.0 (3)°], the two benzene rings make a dihedral angle of 62.09 (14)°. The crystal packing exhibits no significantly short inter-molecular contacts.

Related literature

For general background, see: Nakajima et al. (1998 ▶); Opstal & Verpoort (2003 ▶); Chakraborty & Patel (1996 ▶). For a related structure, see Hu et al. (2008 ▶).

Experimental

Crystal data

C22H16N2OS2

M = 388.49

Monoclinic,

a = 6.0897 (7) Å

b = 41.478 (3) Å

c = 7.5300 (12) Å

β = 90.130 (1)°

V = 1902.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.40 × 0.37 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.891, T max = 0.985

8674 measured reflections

3319 independent reflections

2079 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.090

wR(F 2) = 0.218

S = 1.08

3319 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S1600536809033285/cv2595sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033285/cv2595Isup2.hkl

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

C22H16N2OS2	F(000) = 808
Mr = 388.49	Dx = 1.357 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.0897 (7) Å	Cell parameters from 2059 reflections
b = 41.478 (3) Å	θ = 3.9–25.0°
c = 7.5300 (12) Å	µ = 0.29 mm−1
β = 90.130 (1)°	T = 298 K
V = 1902.0 (4) Å3	Block, red
Z = 4	0.40 × 0.37 × 0.05 mm

Bruker SMART APEX CCD area-detector diffractometer	3319 independent reflections
Radiation source: fine-focus sealed tube	2079 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.891, Tmax = 0.985	k = −49→38
8674 measured reflections	l = −8→7

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)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0631P)2 + 3.3823P] where P = (Fo2 + 2Fc2)/3
3319 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.36 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	0.4955 (3)	0.05770 (4)	0.6056 (3)	0.0906 (6)
S2	0.4773 (3)	0.44248 (5)	0.5080 (3)	0.0998 (7)
N1	0.6149 (7)	0.12778 (10)	0.5599 (6)	0.0552 (11)
N2	0.6082 (7)	0.37230 (10)	0.5480 (6)	0.0529 (11)
O1	0.9917 (5)	0.25041 (8)	0.5517 (5)	0.0489 (8)
C1	0.8811 (7)	0.22122 (11)	0.5554 (6)	0.0409 (11)
C2	0.9821 (7)	0.19597 (11)	0.6410 (6)	0.0443 (12)
H2	1.1137	0.1994	0.7010	0.053*
C3	0.8919 (7)	0.16597 (11)	0.6389 (6)	0.0450 (12)
H3	0.9637	0.1492	0.6969	0.054*
C4	0.6937 (8)	0.15984 (10)	0.5516 (6)	0.0419 (11)
C5	0.5935 (8)	0.18563 (11)	0.4622 (6)	0.0470 (12)
H5	0.4627	0.1822	0.4012	0.056*
C6	0.6854 (8)	0.21602 (11)	0.4629 (6)	0.0451 (12)
H6	0.6177	0.2329	0.4024	0.054*
C7	0.8781 (7)	0.27942 (10)	0.5519 (6)	0.0397 (11)
C8	0.9794 (8)	0.30454 (12)	0.4627 (6)	0.0457 (12)
H8	1.1085	0.3009	0.4001	0.055*
C9	0.8885 (8)	0.33485 (12)	0.4669 (6)	0.0475 (12)
H9	0.9595	0.3519	0.4109	0.057*
C10	0.6885 (7)	0.34028 (11)	0.5557 (6)	0.0412 (11)
C11	0.5918 (8)	0.31457 (11)	0.6446 (6)	0.0473 (12)
H11	0.4615	0.3178	0.7062	0.057*
C12	0.6863 (7)	0.28442 (11)	0.6428 (6)	0.0440 (11)
H12	0.6201	0.2675	0.7032	0.053*
C13	0.4187 (9)	0.12173 (12)	0.5275 (7)	0.0558 (14)
H13	0.3245	0.1384	0.4960	0.067*
C14	0.3329 (9)	0.08851 (12)	0.5382 (7)	0.0556 (14)
C15	0.1330 (9)	0.07893 (13)	0.4965 (8)	0.0655 (16)
H15	0.0224	0.0927	0.4570	0.079*
C16	0.1061 (11)	0.04474 (15)	0.5191 (10)	0.085 (2)
H16	−0.0240	0.0338	0.4956	0.102*
C17	0.2895 (12)	0.03046 (15)	0.5779 (10)	0.084 (2)
H17	0.3025	0.0085	0.6006	0.101*
C18	0.4106 (9)	0.37824 (12)	0.5808 (7)	0.0555 (13)
H18	0.3178	0.3613	0.6101	0.067*
C19	0.3211 (9)	0.41082 (12)	0.5748 (7)	0.0553 (13)
C20	0.1186 (9)	0.42042 (13)	0.6180 (8)	0.0623 (15)
H20	0.0087	0.4065	0.6558	0.075*
C21	0.0893 (11)	0.45432 (15)	0.6002 (9)	0.081 (2)
H21	−0.0408	0.4650	0.6270	0.097*
C22	0.2677 (13)	0.46897 (15)	0.5412 (12)	0.100 (3)
H22	0.2775	0.4910	0.5203	0.120*

	U11	U22	U33	U12	U13	U23
S1	0.0697 (11)	0.0664 (11)	0.1356 (17)	0.0015 (9)	−0.0133 (10)	0.0213 (11)
S2	0.0662 (11)	0.0620 (11)	0.171 (2)	−0.0033 (9)	0.0046 (11)	0.0270 (11)
N1	0.049 (3)	0.052 (3)	0.064 (3)	0.002 (2)	−0.002 (2)	0.004 (2)
N2	0.050 (3)	0.045 (3)	0.064 (3)	−0.001 (2)	0.001 (2)	0.001 (2)
O1	0.0408 (17)	0.0418 (18)	0.064 (2)	−0.0024 (15)	0.0016 (15)	−0.0023 (15)
C1	0.041 (3)	0.040 (3)	0.042 (3)	0.000 (2)	0.003 (2)	−0.001 (2)
C2	0.038 (3)	0.047 (3)	0.047 (3)	0.005 (2)	−0.004 (2)	−0.001 (2)
C3	0.044 (3)	0.045 (3)	0.046 (3)	0.008 (2)	−0.006 (2)	0.007 (2)
C4	0.049 (3)	0.034 (3)	0.043 (3)	0.000 (2)	0.004 (2)	0.002 (2)
C5	0.042 (3)	0.049 (3)	0.050 (3)	−0.003 (2)	−0.012 (2)	0.000 (2)
C6	0.049 (3)	0.041 (3)	0.045 (3)	0.005 (2)	−0.008 (2)	0.004 (2)
C7	0.045 (3)	0.037 (3)	0.038 (3)	0.003 (2)	−0.005 (2)	−0.003 (2)
C8	0.038 (3)	0.052 (3)	0.047 (3)	−0.008 (2)	0.002 (2)	−0.005 (2)
C9	0.048 (3)	0.047 (3)	0.048 (3)	−0.011 (2)	−0.001 (2)	0.006 (2)
C10	0.041 (3)	0.040 (3)	0.043 (3)	−0.001 (2)	−0.005 (2)	−0.002 (2)
C11	0.045 (3)	0.046 (3)	0.050 (3)	0.001 (2)	0.010 (2)	−0.001 (2)
C12	0.044 (3)	0.041 (3)	0.046 (3)	−0.004 (2)	0.008 (2)	0.001 (2)
C13	0.061 (4)	0.047 (3)	0.059 (3)	0.010 (3)	−0.001 (3)	−0.002 (2)
C14	0.062 (3)	0.047 (3)	0.058 (3)	0.001 (3)	0.006 (3)	0.000 (2)
C15	0.061 (4)	0.038 (3)	0.097 (5)	0.001 (3)	−0.022 (3)	0.002 (3)
C16	0.062 (4)	0.063 (4)	0.131 (7)	−0.015 (3)	−0.002 (4)	−0.009 (4)
C17	0.092 (5)	0.041 (4)	0.118 (6)	−0.009 (3)	0.022 (4)	0.013 (3)
C18	0.053 (3)	0.051 (3)	0.062 (3)	−0.007 (3)	−0.003 (3)	0.001 (3)
C19	0.055 (3)	0.050 (3)	0.061 (3)	−0.002 (3)	−0.006 (3)	0.001 (3)
C20	0.057 (3)	0.051 (3)	0.079 (4)	0.000 (3)	0.012 (3)	−0.005 (3)
C21	0.072 (4)	0.066 (4)	0.103 (5)	0.020 (4)	−0.018 (4)	−0.009 (4)
C22	0.089 (5)	0.041 (4)	0.170 (8)	−0.005 (4)	−0.021 (5)	0.006 (4)

S1—C14	1.694 (5)	C8—H8	0.9300
S1—C17	1.701 (7)	C9—C10	1.409 (7)
S2—C19	1.698 (5)	C9—H9	0.9300
S2—C22	1.703 (8)	C10—C11	1.390 (6)
N1—C13	1.244 (6)	C11—C12	1.377 (6)
N1—C4	1.415 (6)	C11—H11	0.9300
N2—C18	1.253 (6)	C12—H12	0.9300
N2—C10	1.416 (6)	C13—C14	1.476 (7)
O1—C1	1.386 (5)	C13—H13	0.9300
O1—C7	1.388 (5)	C14—C15	1.318 (7)
C1—C2	1.374 (6)	C15—C16	1.438 (8)
C1—C6	1.396 (6)	C15—H15	0.9300
C2—C3	1.361 (6)	C16—C17	1.338 (9)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.396 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.458 (7)
C4—C5	1.403 (6)	C18—H18	0.9300
C5—C6	1.379 (6)	C19—C20	1.337 (7)
C5—H5	0.9300	C20—C21	1.423 (8)
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.371 (6)	C21—C22	1.323 (9)
C7—C8	1.385 (6)	C21—H21	0.9300
C8—C9	1.374 (6)	C22—H22	0.9300
C14—S1—C17	91.9 (3)	C12—C11—H11	119.5
C19—S2—C22	92.0 (3)	C10—C11—H11	119.5
C13—N1—C4	120.4 (4)	C7—C12—C11	119.9 (4)
C18—N2—C10	120.5 (4)	C7—C12—H12	120.0
C1—O1—C7	121.0 (3)	C11—C12—H12	120.0
C2—C1—O1	117.3 (4)	N1—C13—C14	121.2 (5)
C2—C1—C6	119.8 (4)	N1—C13—H13	119.4
O1—C1—C6	122.6 (4)	C14—C13—H13	119.4
C3—C2—C1	120.8 (4)	C15—C14—C13	126.5 (5)
C3—C2—H2	119.6	C15—C14—S1	112.5 (4)
C1—C2—H2	119.6	C13—C14—S1	120.9 (4)
C2—C3—C4	121.4 (4)	C14—C15—C16	112.0 (5)
C2—C3—H3	119.3	C14—C15—H15	124.0
C4—C3—H3	119.3	C16—C15—H15	124.0
C3—C4—C5	117.5 (4)	C17—C16—C15	112.4 (6)
C3—C4—N1	116.3 (4)	C17—C16—H16	123.8
C5—C4—N1	126.2 (4)	C15—C16—H16	123.8
C6—C5—C4	121.3 (4)	C16—C17—S1	111.2 (5)
C6—C5—H5	119.4	C16—C17—H17	124.4
C4—C5—H5	119.4	S1—C17—H17	124.4
C5—C6—C1	119.3 (4)	N2—C18—C19	122.3 (5)
C5—C6—H6	120.4	N2—C18—H18	118.8
C1—C6—H6	120.4	C19—C18—H18	118.8
C12—C7—C8	120.6 (4)	C20—C19—C18	127.9 (5)
C12—C7—O1	123.8 (4)	C20—C19—S2	111.1 (4)
C8—C7—O1	115.4 (4)	C18—C19—S2	121.1 (4)
C9—C8—C7	119.8 (4)	C19—C20—C21	112.8 (5)
C9—C8—H8	120.1	C19—C20—H20	123.6
C7—C8—H8	120.1	C21—C20—H20	123.6
C8—C9—C10	120.4 (4)	C22—C21—C20	112.5 (6)
C8—C9—H9	119.8	C22—C21—H21	123.8
C10—C9—H9	119.8	C20—C21—H21	123.8
C11—C10—C9	118.2 (4)	C21—C22—S2	111.7 (5)
C11—C10—N2	126.3 (4)	C21—C22—H22	124.2
C9—C10—N2	115.4 (4)	S2—C22—H22	124.2
C12—C11—C10	121.0 (4)
C7—O1—C1—C2	−148.1 (4)	N2—C10—C11—C12	−179.8 (4)
C7—O1—C1—C6	38.0 (7)	C8—C7—C12—C11	0.5 (7)
O1—C1—C2—C3	−175.0 (4)	O1—C7—C12—C11	175.9 (4)
C6—C1—C2—C3	−1.0 (7)	C10—C11—C12—C7	−0.2 (7)
C1—C2—C3—C4	−0.5 (7)	C4—N1—C13—C14	−179.1 (4)
C2—C3—C4—C5	1.5 (7)	N1—C13—C14—C15	−175.5 (6)
C2—C3—C4—N1	−179.4 (4)	N1—C13—C14—S1	3.3 (7)
C13—N1—C4—C3	161.5 (5)	C17—S1—C14—C15	−0.1 (5)
C13—N1—C4—C5	−19.6 (8)	C17—S1—C14—C13	−179.0 (5)
C3—C4—C5—C6	−1.1 (7)	C13—C14—C15—C16	178.8 (6)
N1—C4—C5—C6	−180.0 (5)	S1—C14—C15—C16	−0.1 (7)
C4—C5—C6—C1	−0.4 (7)	C14—C15—C16—C17	0.2 (9)
C2—C1—C6—C5	1.4 (7)	C15—C16—C17—S1	−0.3 (8)
O1—C1—C6—C5	175.2 (4)	C14—S1—C17—C16	0.2 (6)
C1—O1—C7—C12	35.5 (6)	C10—N2—C18—C19	179.9 (5)
C1—O1—C7—C8	−148.9 (4)	N2—C18—C19—C20	−175.2 (6)
C12—C7—C8—C9	0.8 (7)	N2—C18—C19—S2	4.4 (8)
O1—C7—C8—C9	−175.0 (4)	C22—S2—C19—C20	0.6 (5)
C7—C8—C9—C10	−2.5 (7)	C22—S2—C19—C18	−179.1 (5)
C8—C9—C10—C11	2.8 (7)	C18—C19—C20—C21	178.5 (5)
C8—C9—C10—N2	−178.7 (4)	S2—C19—C20—C21	−1.1 (7)
C18—N2—C10—C11	−19.9 (7)	C19—C20—C21—C22	1.2 (9)
C18—N2—C10—C9	161.6 (5)	C20—C21—C22—S2	−0.8 (9)
C9—C10—C11—C12	−1.4 (7)	C19—S2—C22—C21	0.1 (6)