N'(2),N'(5)-Bis[(E)-2-hy-droxy-benzyl-idene]-3,4-dimethyl-thio-phene-2,5-dicarbohydrazide.

In the title mol-ecule, C(22)H(20)N(4)O(4)S, both C=N bonds are in an E conformation. The benzene rings form dihedral angles of 12.10 (13) and 25.17 (12)° with the thio-phene ring. The dihedral angle between the two benzene rings is 17.59 (14)°. There are two intra-molecular O-H⋯N hydrogen bonds. In the crystal, N-H⋯O hydrogen bonds connect mol-ecules into chains along [010].

Related literature

For the medicinal properties of thio­phene derivatives, see: Bondock et al. (2010 ▶); Geng & Zhou (2008 ▶). For a related structure, see: Tang et al. (2010 ▶).

Experimental

Crystal data

C22H20N4O4S

M = 436.48

Triclinic,

a = 8.392 (8) Å

b = 9.511 (9) Å

c = 12.937 (8) Å

α = 99.853 (17)°

β = 90.804 (18)°

γ = 92.374 (18)°

V = 1016.2 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.19 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.969

5573 measured reflections

3925 independent reflections

2660 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.02

3925 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812020260/lh5463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020260/lh5463Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020260/lh5463Isup3.cml

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

C22H20N4O4S	Z = 2
Mr = 436.48	F(000) = 456
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.392 (8) Å	Cell parameters from 1480 reflections
b = 9.511 (9) Å	θ = 2.9–24.4°
c = 12.937 (8) Å	µ = 0.20 mm−1
α = 99.853 (17)°	T = 296 K
β = 90.804 (18)°	Block, yellow
γ = 92.374 (18)°	0.19 × 0.18 × 0.16 mm
V = 1016.2 (15) Å3

Bruker APEXII CCD diffractometer	3925 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→10
Tmin = 0.963, Tmax = 0.969	k = −11→10
5573 measured reflections	l = −15→15

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0604P)2 + 0.0881P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3925 reflections	Δρmax = 0.23 e Å−3
283 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (17)

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
N1	0.9005 (2)	0.2862 (2)	0.73465 (15)	0.0457 (5)
N2	0.8176 (2)	0.32288 (19)	0.65213 (15)	0.0463 (6)
H2	0.8112	0.4109	0.6455	0.056*
N3	0.0145 (2)	0.15155 (19)	0.30284 (15)	0.0423 (5)
N4	0.1633 (2)	0.16130 (19)	0.34807 (16)	0.0448 (5)
H4	0.1990	0.0926	0.3759	0.054*
C1	1.0429 (3)	0.2314 (3)	0.92331 (19)	0.0473 (6)
C2	1.1287 (4)	0.2087 (3)	1.0091 (2)	0.0631 (8)
H2A	1.1110	0.1251	1.0363	0.076*
C3	1.2397 (4)	0.3085 (4)	1.0542 (2)	0.0702 (9)
H3A	1.2992	0.2919	1.1118	0.084*
C4	1.2661 (4)	0.4336 (4)	1.0168 (2)	0.0658 (8)
H4A	1.3424	0.5014	1.0488	0.079*
C5	1.1795 (3)	0.4575 (3)	0.9320 (2)	0.0524 (7)
H5A	1.1958	0.5429	0.9071	0.063*
C6	1.0681 (3)	0.3567 (3)	0.88285 (18)	0.0424 (6)
C7	0.9818 (3)	0.3853 (3)	0.79290 (18)	0.0432 (6)
H7A	0.9854	0.4772	0.7771	0.052*
C8	0.7473 (3)	0.2195 (2)	0.5826 (2)	0.0438 (6)
C9	0.6441 (3)	0.2671 (2)	0.50316 (18)	0.0392 (6)
C10	0.6698 (3)	0.3655 (2)	0.44024 (17)	0.0365 (5)
C11	0.8216 (3)	0.4475 (3)	0.4339 (2)	0.0482 (6)
H11A	0.8974	0.4238	0.4837	0.072*
H11B	0.8035	0.5479	0.4493	0.072*
H11C	0.8626	0.4242	0.3644	0.072*
C12	0.5355 (3)	0.3773 (2)	0.37593 (16)	0.0348 (5)
C13	0.5400 (3)	0.4737 (3)	0.29632 (19)	0.0482 (6)
H13A	0.4382	0.4681	0.2607	0.072*
H13B	0.6210	0.4448	0.2464	0.072*
H13C	0.5636	0.5702	0.3306	0.072*
C14	0.4126 (3)	0.2878 (2)	0.39320 (17)	0.0356 (5)
C15	0.2514 (3)	0.2808 (2)	0.34768 (17)	0.0364 (5)
C16	−0.0755 (3)	0.0451 (2)	0.31184 (19)	0.0454 (6)
H16A	−0.0433	−0.0200	0.3532	0.055*
C17	−0.2275 (3)	0.0243 (3)	0.25834 (19)	0.0452 (6)
C18	−0.2791 (3)	0.1158 (3)	0.1937 (2)	0.0490 (7)
C19	−0.4226 (4)	0.0886 (4)	0.1412 (2)	0.0686 (9)
H19A	−0.4569	0.1500	0.0975	0.082*
C20	−0.5150 (4)	−0.0277 (4)	0.1529 (3)	0.0798 (11)
H20A	−0.6133	−0.0446	0.1179	0.096*
C21	−0.4657 (4)	−0.1201 (4)	0.2151 (3)	0.0795 (10)
H21A	−0.5291	−0.2005	0.2218	0.095*
C22	−0.3236 (4)	−0.0936 (3)	0.2669 (2)	0.0639 (8)
H22A	−0.2900	−0.1568	0.3094	0.077*
O1	0.9338 (3)	0.13019 (19)	0.88189 (15)	0.0640 (6)
H1	0.8908	0.1536	0.8305	0.096*
O2	0.7611 (2)	0.09444 (16)	0.58491 (16)	0.0683 (6)
O3	0.1986 (2)	0.38046 (15)	0.31228 (12)	0.0443 (4)
O4	−0.1926 (2)	0.2321 (2)	0.17967 (17)	0.0681 (6)
H4B	−0.1073	0.2355	0.2119	0.102*
S1	0.46125 (8)	0.18434 (6)	0.48365 (5)	0.0450 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0422 (13)	0.0467 (11)	0.0497 (12)	0.0023 (10)	−0.0194 (10)	0.0140 (9)
N2	0.0483 (13)	0.0348 (10)	0.0563 (13)	−0.0007 (9)	−0.0264 (11)	0.0116 (9)
N3	0.0329 (11)	0.0371 (10)	0.0555 (13)	0.0001 (9)	−0.0143 (10)	0.0054 (9)
N4	0.0351 (12)	0.0350 (10)	0.0654 (14)	−0.0012 (9)	−0.0191 (10)	0.0139 (9)
C1	0.0444 (16)	0.0562 (15)	0.0425 (14)	0.0076 (13)	−0.0018 (12)	0.0105 (12)
C2	0.068 (2)	0.0745 (19)	0.0507 (17)	0.0153 (17)	−0.0077 (15)	0.0200 (15)
C3	0.066 (2)	0.100 (2)	0.0455 (17)	0.022 (2)	−0.0139 (15)	0.0112 (17)
C4	0.0513 (18)	0.090 (2)	0.0512 (17)	0.0001 (17)	−0.0179 (14)	−0.0003 (16)
C5	0.0446 (16)	0.0620 (16)	0.0495 (15)	−0.0029 (13)	−0.0072 (13)	0.0081 (13)
C6	0.0372 (14)	0.0525 (14)	0.0378 (13)	0.0056 (12)	−0.0054 (11)	0.0087 (11)
C7	0.0417 (15)	0.0443 (13)	0.0445 (14)	0.0030 (12)	−0.0087 (12)	0.0103 (11)
C8	0.0358 (14)	0.0387 (12)	0.0574 (15)	−0.0030 (11)	−0.0172 (12)	0.0126 (11)
C9	0.0329 (13)	0.0339 (11)	0.0493 (14)	−0.0015 (10)	−0.0148 (11)	0.0053 (10)
C10	0.0332 (13)	0.0350 (11)	0.0390 (13)	0.0008 (10)	−0.0045 (10)	0.0007 (10)
C11	0.0361 (14)	0.0584 (15)	0.0488 (15)	−0.0058 (12)	−0.0059 (12)	0.0083 (12)
C12	0.0338 (13)	0.0354 (11)	0.0338 (12)	0.0009 (10)	−0.0044 (10)	0.0031 (9)
C13	0.0444 (15)	0.0530 (14)	0.0494 (15)	−0.0021 (12)	−0.0073 (12)	0.0169 (12)
C14	0.0347 (13)	0.0327 (11)	0.0390 (13)	0.0016 (10)	−0.0090 (10)	0.0057 (9)
C15	0.0369 (13)	0.0328 (11)	0.0380 (12)	0.0016 (10)	−0.0082 (10)	0.0028 (10)
C16	0.0406 (15)	0.0412 (13)	0.0547 (15)	−0.0008 (12)	−0.0119 (12)	0.0107 (11)
C17	0.0340 (14)	0.0495 (14)	0.0494 (15)	−0.0022 (12)	−0.0052 (12)	0.0028 (12)
C18	0.0382 (15)	0.0529 (15)	0.0542 (16)	0.0047 (13)	−0.0055 (12)	0.0039 (12)
C19	0.0429 (18)	0.091 (2)	0.069 (2)	0.0100 (18)	−0.0190 (15)	0.0056 (17)
C20	0.0352 (17)	0.114 (3)	0.079 (2)	−0.0092 (19)	−0.0133 (16)	−0.011 (2)
C21	0.050 (2)	0.096 (2)	0.086 (2)	−0.0327 (18)	−0.0060 (18)	0.008 (2)
C22	0.0540 (19)	0.0697 (18)	0.0668 (19)	−0.0183 (15)	−0.0059 (15)	0.0136 (15)
O1	0.0706 (15)	0.0566 (11)	0.0683 (14)	−0.0086 (11)	−0.0167 (11)	0.0253 (10)
O2	0.0728 (15)	0.0334 (9)	0.0996 (15)	−0.0046 (9)	−0.0467 (12)	0.0197 (9)
O3	0.0427 (10)	0.0366 (8)	0.0548 (10)	0.0001 (8)	−0.0179 (8)	0.0135 (7)
O4	0.0557 (13)	0.0601 (11)	0.0935 (16)	0.0018 (10)	−0.0228 (11)	0.0293 (11)
S1	0.0398 (4)	0.0391 (3)	0.0577 (4)	−0.0084 (3)	−0.0212 (3)	0.0167 (3)

N1—C7	1.270 (3)	C11—H11A	0.9600
N1—N2	1.368 (3)	C11—H11B	0.9600
N2—C8	1.326 (3)	C11—H11C	0.9600
N2—H2	0.8600	C12—C14	1.355 (3)
N3—C16	1.261 (3)	C12—C13	1.491 (3)
N3—N4	1.365 (3)	C13—H13A	0.9600
N4—C15	1.331 (3)	C13—H13B	0.9600
N4—H4	0.8600	C13—H13C	0.9600
C1—O1	1.337 (3)	C14—C15	1.462 (3)
C1—C2	1.368 (3)	C14—S1	1.708 (2)
C1—C6	1.391 (4)	C15—O3	1.217 (3)
C2—C3	1.354 (4)	C16—C17	1.432 (3)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.370 (4)	C17—C22	1.375 (4)
C3—H3A	0.9300	C17—C18	1.384 (4)
C4—C5	1.364 (4)	C18—O4	1.338 (3)
C4—H4A	0.9300	C18—C19	1.367 (4)
C5—C6	1.377 (3)	C19—C20	1.355 (5)
C5—H5A	0.9300	C19—H19A	0.9300
C6—C7	1.433 (3)	C20—C21	1.361 (5)
C7—H7A	0.9300	C20—H20A	0.9300
C8—O2	1.205 (3)	C21—C22	1.354 (4)
C8—C9	1.476 (3)	C21—H21A	0.9300
C9—C10	1.355 (3)	C22—H22A	0.9300
C9—S1	1.690 (3)	O1—H1	0.8200
C10—C12	1.411 (3)	O4—H4B	0.8200
C10—C11	1.477 (4)
C7—N1—N2	117.0 (2)	H11A—C11—H11C	109.5
C8—N2—N1	118.42 (19)	H11B—C11—H11C	109.5
C8—N2—H2	120.8	C14—C12—C10	111.9 (2)
N1—N2—H2	120.8	C14—C12—C13	126.7 (2)
C16—N3—N4	118.1 (2)	C10—C12—C13	121.3 (2)
C15—N4—N3	117.69 (19)	C12—C13—H13A	109.5
C15—N4—H4	121.2	C12—C13—H13B	109.5
N3—N4—H4	121.2	H13A—C13—H13B	109.5
O1—C1—C2	117.5 (3)	C12—C13—H13C	109.5
O1—C1—C6	122.1 (2)	H13A—C13—H13C	109.5
C2—C1—C6	120.4 (3)	H13B—C13—H13C	109.5
C3—C2—C1	119.6 (3)	C12—C14—C15	126.6 (2)
C3—C2—H2A	120.2	C12—C14—S1	112.18 (17)
C1—C2—H2A	120.2	C15—C14—S1	121.11 (18)
C2—C3—C4	121.3 (3)	O3—C15—N4	121.2 (2)
C2—C3—H3A	119.4	O3—C15—C14	121.7 (2)
C4—C3—H3A	119.4	N4—C15—C14	117.08 (19)
C5—C4—C3	119.3 (3)	N3—C16—C17	119.9 (2)
C5—C4—H4A	120.3	N3—C16—H16A	120.0
C3—C4—H4A	120.3	C17—C16—H16A	120.0
C4—C5—C6	120.9 (3)	C22—C17—C18	118.1 (3)
C4—C5—H5A	119.6	C22—C17—C16	119.6 (2)
C6—C5—H5A	119.6	C18—C17—C16	122.3 (2)
C5—C6—C1	118.5 (2)	O4—C18—C19	117.7 (3)
C5—C6—C7	119.0 (2)	O4—C18—C17	122.2 (2)
C1—C6—C7	122.6 (2)	C19—C18—C17	120.1 (3)
N1—C7—C6	120.5 (2)	C20—C19—C18	120.0 (3)
N1—C7—H7A	119.8	C20—C19—H19A	120.0
C6—C7—H7A	119.8	C18—C19—H19A	120.0
O2—C8—N2	123.2 (2)	C19—C20—C21	120.9 (3)
O2—C8—C9	121.3 (2)	C19—C20—H20A	119.6
N2—C8—C9	115.5 (2)	C21—C20—H20A	119.6
C10—C9—C8	131.5 (2)	C22—C21—C20	119.2 (3)
C10—C9—S1	112.63 (17)	C22—C21—H21A	120.4
C8—C9—S1	115.89 (19)	C20—C21—H21A	120.4
C9—C10—C12	112.1 (2)	C21—C22—C17	121.6 (3)
C9—C10—C11	125.2 (2)	C21—C22—H22A	119.2
C12—C10—C11	122.6 (2)	C17—C22—H22A	119.2
C10—C11—H11A	109.5	C1—O1—H1	109.5
C10—C11—H11B	109.5	C18—O4—H4B	109.5
H11A—C11—H11B	109.5	C9—S1—C14	91.09 (12)
C10—C11—H11C	109.5
C7—N1—N2—C8	172.0 (2)	C11—C10—C12—C13	0.5 (3)
C16—N3—N4—C15	−173.2 (2)	C10—C12—C14—C15	174.1 (2)
O1—C1—C2—C3	−179.5 (3)	C13—C12—C14—C15	−9.0 (4)
C6—C1—C2—C3	−0.5 (4)	C10—C12—C14—S1	−2.3 (2)
C1—C2—C3—C4	1.1 (5)	C13—C12—C14—S1	174.64 (18)
C2—C3—C4—C5	−0.4 (5)	N3—N4—C15—O3	3.1 (3)
C3—C4—C5—C6	−1.1 (4)	N3—N4—C15—C14	−178.0 (2)
C4—C5—C6—C1	1.6 (4)	C12—C14—C15—O3	−20.8 (4)
C4—C5—C6—C7	−178.9 (2)	S1—C14—C15—O3	155.27 (18)
O1—C1—C6—C5	178.1 (2)	C12—C14—C15—N4	160.2 (2)
C2—C1—C6—C5	−0.9 (4)	S1—C14—C15—N4	−23.7 (3)
O1—C1—C6—C7	−1.3 (4)	N4—N3—C16—C17	−174.8 (2)
C2—C1—C6—C7	179.7 (2)	N3—C16—C17—C22	178.7 (2)
N2—N1—C7—C6	178.1 (2)	N3—C16—C17—C18	1.8 (4)
C5—C6—C7—N1	167.1 (2)	C22—C17—C18—O4	−179.2 (3)
C1—C6—C7—N1	−13.4 (4)	C16—C17—C18—O4	−2.2 (4)
N1—N2—C8—O2	−4.8 (4)	C22—C17—C18—C19	0.6 (4)
N1—N2—C8—C9	172.8 (2)	C16—C17—C18—C19	177.6 (2)
O2—C8—C9—C10	−133.2 (3)	O4—C18—C19—C20	−179.9 (3)
N2—C8—C9—C10	49.2 (4)	C17—C18—C19—C20	0.3 (4)
O2—C8—C9—S1	45.7 (3)	C18—C19—C20—C21	−1.1 (5)
N2—C8—C9—S1	−132.0 (2)	C19—C20—C21—C22	1.0 (5)
C8—C9—C10—C12	−179.5 (2)	C20—C21—C22—C17	0.0 (5)
S1—C9—C10—C12	1.6 (2)	C18—C17—C22—C21	−0.8 (4)
C8—C9—C10—C11	3.4 (4)	C16—C17—C22—C21	−177.8 (3)
S1—C9—C10—C11	−175.46 (18)	C10—C9—S1—C14	−2.47 (18)
C9—C10—C12—C14	0.4 (3)	C8—C9—S1—C14	178.49 (18)
C11—C10—C12—C14	177.6 (2)	C12—C14—S1—C9	2.72 (17)
C9—C10—C12—C13	−176.7 (2)	C15—C14—S1—C9	−173.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.626 (4)	145
N2—H2···O3i	0.86	1.97	2.789 (4)	159
N4—H4···O2ii	0.86	1.97	2.812 (4)	165
O4—H4B···N3	0.82	1.85	2.569 (4)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.91	2.626 (4)	145
N2—H2⋯O3i	0.86	1.97	2.789 (4)	159
N4—H4⋯O2ii	0.86	1.97	2.812 (4)	165
O4—H4B⋯N3	0.82	1.85	2.569 (4)	146

Symmetry codes: (i) ; (ii) .