(E,E)-N'-{4-[(2-Benzoyl-hydrazin-1-yl-idene)meth-yl]benzyl-idene}benzo-hydrazide.

In the title compound, C(22)H(18)N(4)O(2), the mol-ecules lie across an inversion centre. The dihedral angle between the mean planes of the central and terminal benzene rings is 66.03 (2)°. The mol-ecule displays trans and anti conformations about the C=N and N-N bonds, respectively. In the crystal, N-H⋯O hydrogen bonds, with the O atoms of C=O groups acting as acceptors, link the mol-ecules into a chain along [101].

Related literature

For historical background to aroylhydrazones, see: Savanini et al. (2002 ▶). For related structures, see: Bikas et al. (2012 ▶, 2010a ▶,b ▶); Hosseini Monfared et al. (2010a ▶). For catalytic applications of aroylhydrazones, see: Hosseini Monfared et al. (2010b ▶).

Experimental

Crystal data

C22H18N4O2

M = 370.40

Monoclinic,

a = 30.569 (3) Å

b = 5.1845 (3) Å

c = 12.5191 (11) Å

β = 112.408 (7)°

V = 1834.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.42 × 0.22 × 0.08 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.976, T max = 0.992

13265 measured reflections

1905 independent reflections

965 reflections with I > 2σ(I)

R int = 0.105

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.078

S = 0.94

1905 reflections

163 parameters

All H-atom parameters refined

Δρmax = 0.11 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014687/qm2059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014687/qm2059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014687/qm2059Isup3.cml

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

C22H18N4O2	F(000) = 776
Mr = 370.40	Dx = 1.341 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8004 reflections
a = 30.569 (3) Å	θ = 1.4–27.5°
b = 5.1845 (3) Å	µ = 0.09 mm−1
c = 12.5191 (11) Å	T = 293 K
β = 112.408 (7)°	Prism, colorless
V = 1834.3 (3) Å3	0.42 × 0.22 × 0.08 mm
Z = 4

Stoe IPDS 2 diffractometer	1905 independent reflections
Radiation source: fine-focus sealed tube	965 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.105
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 1.4°
rotation method scans	h = −38→38
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −6→6
Tmin = 0.976, Tmax = 0.992	l = −15→15
13265 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	All H-atom parameters refined
S = 0.94	w = 1/[σ2(Fo2) + (0.0207P)2] where P = (Fo2 + 2Fc2)/3
1905 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.14 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	0.84753 (7)	0.1985 (4)	0.32678 (19)	0.0454 (6)
C2	0.84744 (9)	0.3457 (5)	0.4191 (2)	0.0562 (7)
C3	0.81956 (9)	0.2794 (6)	0.4790 (2)	0.0658 (8)
C4	0.79059 (10)	0.0693 (6)	0.4454 (3)	0.0695 (8)
C5	0.78956 (10)	−0.0782 (5)	0.3532 (3)	0.0711 (8)
C6	0.81817 (8)	−0.0140 (5)	0.2948 (2)	0.0582 (7)
C7	0.87799 (7)	0.2804 (4)	0.26408 (19)	0.0475 (6)
C8	0.94196 (8)	−0.0556 (5)	0.1321 (2)	0.0502 (6)
C10	0.96656 (9)	0.1846 (5)	−0.0081 (2)	0.0558 (7)
C11	1.00525 (9)	−0.2099 (5)	0.0707 (2)	0.0553 (7)
C12	0.97114 (7)	−0.0250 (4)	0.06315 (18)	0.0458 (6)
N1	0.89465 (7)	0.0866 (4)	0.21865 (17)	0.0543 (6)
N2	0.92141 (7)	0.1407 (3)	0.15428 (16)	0.0516 (5)
O1	0.88701 (6)	0.5082 (3)	0.25515 (14)	0.0650 (5)
H1	0.8912 (7)	−0.074 (4)	0.2351 (18)	0.055 (7)*
H2	0.9404 (6)	−0.232 (4)	0.1624 (16)	0.052 (6)*
H3	0.8174 (7)	−0.118 (4)	0.2312 (19)	0.058 (7)*
H4	0.9424 (8)	0.305 (4)	−0.0167 (18)	0.065 (7)*
H5	1.0094 (7)	−0.343 (4)	0.1209 (18)	0.056 (7)*
H6	0.8219 (8)	0.387 (4)	0.546 (2)	0.078 (8)*
H7	0.8670 (7)	0.499 (4)	0.4386 (17)	0.068 (7)*
H8	0.7688 (9)	−0.228 (5)	0.324 (2)	0.101 (10)*
H9	0.7717 (9)	0.017 (5)	0.489 (2)	0.096 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0450 (14)	0.0457 (13)	0.0519 (16)	0.0066 (11)	0.0255 (13)	0.0039 (12)
C2	0.0568 (16)	0.0572 (16)	0.0627 (18)	−0.0026 (13)	0.0319 (15)	−0.0062 (13)
C3	0.0676 (17)	0.0798 (19)	0.0621 (19)	0.0055 (16)	0.0385 (17)	−0.0027 (16)
C4	0.0691 (19)	0.0738 (19)	0.084 (2)	0.0066 (15)	0.0495 (18)	0.0112 (17)
C5	0.0715 (19)	0.0601 (17)	0.099 (2)	−0.0068 (15)	0.0518 (19)	−0.0044 (17)
C6	0.0618 (15)	0.0521 (14)	0.0735 (19)	−0.0023 (13)	0.0401 (15)	−0.0111 (15)
C7	0.0477 (13)	0.0479 (14)	0.0513 (16)	0.0053 (12)	0.0239 (12)	0.0012 (12)
C8	0.0532 (15)	0.0486 (16)	0.0569 (16)	0.0007 (12)	0.0301 (13)	−0.0008 (12)
C10	0.0580 (16)	0.0553 (15)	0.0662 (18)	0.0137 (13)	0.0375 (15)	0.0052 (13)
C11	0.0655 (16)	0.0507 (14)	0.0605 (18)	0.0083 (13)	0.0362 (15)	0.0045 (13)
C12	0.0454 (14)	0.0483 (13)	0.0504 (15)	−0.0004 (12)	0.0259 (12)	−0.0059 (12)
N1	0.0648 (14)	0.0476 (12)	0.0704 (15)	0.0036 (11)	0.0481 (13)	0.0054 (11)
N2	0.0531 (12)	0.0537 (12)	0.0599 (13)	0.0006 (9)	0.0349 (11)	−0.0002 (10)
O1	0.0857 (12)	0.0445 (9)	0.0850 (13)	−0.0003 (9)	0.0552 (10)	0.0020 (9)

C1—C6	1.381 (3)	C7—N1	1.346 (3)
C1—C2	1.386 (3)	C8—N2	1.281 (3)
C1—C7	1.490 (3)	C8—C12	1.467 (3)
C2—C3	1.377 (3)	C8—H2	1.00 (2)
C2—H7	0.97 (2)	C10—C11i	1.375 (3)
C3—C4	1.365 (4)	C10—C12	1.379 (3)
C3—H6	0.99 (2)	C10—H4	0.94 (2)
C4—C5	1.374 (3)	C11—C10i	1.375 (3)
C4—H9	0.98 (3)	C11—C12	1.392 (3)
C5—C6	1.378 (3)	C11—H5	0.91 (2)
C5—H8	0.98 (3)	N1—N2	1.378 (2)
C6—H3	0.95 (2)	N1—H1	0.87 (2)
C7—O1	1.228 (2)
C6—C1—C2	118.3 (2)	O1—C7—C1	121.95 (19)
C6—C1—C7	122.8 (2)	N1—C7—C1	115.0 (2)
C2—C1—C7	118.9 (2)	N2—C8—C12	120.0 (2)
C3—C2—C1	121.0 (3)	N2—C8—H2	123.2 (11)
C3—C2—H7	121.3 (13)	C12—C8—H2	116.7 (11)
C1—C2—H7	117.7 (13)	C11i—C10—C12	120.8 (2)
C4—C3—C2	119.6 (3)	C11i—C10—H4	120.5 (13)
C4—C3—H6	122.6 (14)	C12—C10—H4	118.5 (13)
C2—C3—H6	117.8 (14)	C10i—C11—C12	120.8 (2)
C3—C4—C5	120.5 (3)	C10i—C11—H5	120.9 (13)
C3—C4—H9	120.0 (15)	C12—C11—H5	118.2 (13)
C5—C4—H9	119.4 (15)	C10—C12—C11	118.4 (2)
C4—C5—C6	119.7 (3)	C10—C12—C8	122.1 (2)
C4—C5—H8	124.0 (17)	C11—C12—C8	119.5 (2)
C6—C5—H8	116.3 (17)	C7—N1—N2	120.0 (2)
C5—C6—C1	120.8 (3)	C7—N1—H1	120.9 (14)
C5—C6—H3	119.3 (13)	N2—N1—H1	118.9 (14)
C1—C6—H3	119.9 (13)	C8—N2—N1	114.51 (19)
O1—C7—N1	123.0 (2)
C6—C1—C2—C3	1.3 (4)	C2—C1—C7—N1	149.0 (2)
C7—C1—C2—C3	179.4 (2)	C11i—C10—C12—C11	0.4 (4)
C1—C2—C3—C4	−1.7 (4)	C11i—C10—C12—C8	179.2 (2)
C2—C3—C4—C5	0.9 (4)	C10i—C11—C12—C10	−0.4 (4)
C3—C4—C5—C6	0.3 (4)	C10i—C11—C12—C8	−179.3 (2)
C4—C5—C6—C1	−0.7 (4)	N2—C8—C12—C10	−20.1 (3)
C2—C1—C6—C5	−0.1 (4)	N2—C8—C12—C11	158.7 (2)
C7—C1—C6—C5	−178.1 (2)	O1—C7—N1—N2	−3.0 (3)
C6—C1—C7—O1	147.0 (2)	C1—C7—N1—N2	177.04 (19)
C2—C1—C7—O1	−30.9 (3)	C12—C8—N2—N1	179.3 (2)
C6—C1—C7—N1	−33.0 (3)	C7—N1—N2—C8	168.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ii	0.87 (2)	2.19 (2)	3.056 (3)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (2)	2.19 (2)	3.056 (3)	171 (2)

Symmetry code: (i) .