(E)-2,4-Dimethyl-N'-(2-methyl-benzyl-idene)benzohydrazide.

In the title benzoyl-hydrazide derivative, C17H18N2O, the dihedral angle between the benzene rings is 88.45 (8)° and the azomethine double bond adopts an E conformation. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming a chain along the b axis.

Related literature

For the applications and biological activity of Schiff bases, see: Musharraf et al. (2012 ▶); Khan et al. (2012 ▶). For the crystal structures of related compounds, see: Taha et al. (2012a ▶,b ▶); Naz et al. (2012 ▶).

Experimental

Crystal data

C17H18N2O

M = 266.33

Orthorhombic,

a = 26.1151 (10) Å

b = 4.9484 (2) Å

c = 11.3933 (4) Å

V = 1472.33 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 273 K

0.56 × 0.55 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.983

8023 measured reflections

2577 independent reflections

2483 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.04

2577 reflections

189 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004388/is5246sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004388/is5246Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004388/is5246Isup3.cml

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

C17H18N2O	F(000) = 568
Mr = 266.33	Dx = 1.202 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4590 reflections
a = 26.1151 (10) Å	θ = 2.4–27.4°
b = 4.9484 (2) Å	µ = 0.08 mm−1
c = 11.3933 (4) Å	T = 273 K
V = 1472.33 (10) Å3	Block, colorles
Z = 4	0.56 × 0.55 × 0.23 mm

Bruker SMART APEX CCD area-detector diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2483 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scan	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −25→31
Tmin = 0.959, Tmax = 0.983	k = −5→5
8023 measured reflections	l = −13→13

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.1205P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2577 reflections	Δρmax = 0.12 e Å−3
189 parameters	Δρmin = −0.14 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

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
O1	0.40241 (5)	0.5493 (2)	0.43046 (18)	0.0938 (6)
N1	0.38352 (4)	0.1086 (2)	0.44326 (11)	0.0438 (3)
H1A	0.3925 (5)	−0.050 (3)	0.4301 (13)	0.039 (4)*
N2	0.33498 (4)	0.1558 (2)	0.48752 (10)	0.0448 (3)
C1	0.49419 (6)	0.0399 (3)	0.44104 (14)	0.0500 (3)
H1B	0.4797	−0.0346	0.5082	0.060*
C2	0.54235 (6)	−0.0412 (3)	0.40641 (15)	0.0600 (4)
H2B	0.5601	−0.1679	0.4510	0.072*
C3	0.56461 (6)	0.0633 (4)	0.30653 (15)	0.0605 (4)
C4	0.53740 (6)	0.2556 (4)	0.24413 (14)	0.0588 (4)
H4A	0.5524	0.3297	0.1775	0.071*
C5	0.48869 (6)	0.3437 (3)	0.27612 (13)	0.0488 (4)
C6	0.46699 (5)	0.2308 (3)	0.37737 (12)	0.0426 (3)
C7	0.41514 (5)	0.3145 (3)	0.41905 (14)	0.0480 (3)
C8	0.30625 (5)	−0.0517 (3)	0.49163 (13)	0.0459 (3)
H8A	0.3181	−0.2157	0.4624	0.055*
C9	0.25464 (5)	−0.0345 (3)	0.54203 (13)	0.0458 (3)
C10	0.24424 (6)	0.1476 (3)	0.63203 (14)	0.0553 (4)
H10A	0.2703	0.2579	0.6602	0.066*
C11	0.19599 (7)	0.1674 (4)	0.68005 (15)	0.0656 (5)
H11A	0.1893	0.2922	0.7392	0.079*
C12	0.15778 (7)	0.0008 (4)	0.63967 (17)	0.0665 (5)
H12A	0.1252	0.0108	0.6722	0.080*
C13	0.16772 (6)	−0.1808 (3)	0.55115 (18)	0.0628 (4)
H13A	0.1414	−0.2922	0.5248	0.075*
C14	0.21564 (5)	−0.2029 (3)	0.50006 (14)	0.0500 (3)
C15	0.22448 (7)	−0.3941 (3)	0.39994 (17)	0.0652 (4)
H15A	0.1940	−0.4979	0.3862	0.098*
H15B	0.2522	−0.5136	0.4189	0.098*
H15C	0.2329	−0.2933	0.3306	0.098*
C16	0.61613 (7)	−0.0348 (6)	0.2648 (2)	0.0969 (8)
H16A	0.6383	−0.0606	0.3311	0.145*
H16B	0.6308	0.0969	0.2129	0.145*
H16C	0.6120	−0.2030	0.2239	0.145*
C17	0.46107 (8)	0.5471 (4)	0.20175 (18)	0.0736 (5)
H17A	0.4250	0.5091	0.2028	0.110*
H17B	0.4735	0.5370	0.1226	0.110*
H17C	0.4670	0.7251	0.2323	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0731 (8)	0.0328 (5)	0.1753 (17)	0.0011 (5)	0.0407 (10)	−0.0067 (8)
N1	0.0394 (6)	0.0335 (5)	0.0587 (7)	0.0032 (4)	0.0055 (5)	−0.0042 (5)
N2	0.0388 (6)	0.0451 (6)	0.0505 (6)	0.0038 (5)	0.0034 (5)	−0.0020 (5)
C1	0.0471 (8)	0.0556 (8)	0.0472 (8)	−0.0015 (6)	0.0033 (7)	0.0003 (7)
C2	0.0467 (8)	0.0745 (10)	0.0586 (10)	0.0108 (7)	−0.0058 (8)	−0.0036 (8)
C3	0.0421 (8)	0.0810 (11)	0.0583 (9)	−0.0034 (7)	0.0019 (8)	−0.0175 (8)
C4	0.0589 (10)	0.0728 (10)	0.0448 (8)	−0.0218 (8)	0.0111 (7)	−0.0100 (7)
C5	0.0555 (9)	0.0431 (7)	0.0477 (8)	−0.0127 (6)	−0.0011 (7)	−0.0043 (6)
C6	0.0429 (7)	0.0367 (6)	0.0482 (8)	−0.0057 (5)	0.0015 (6)	−0.0066 (5)
C7	0.0460 (8)	0.0349 (6)	0.0630 (9)	−0.0006 (5)	0.0038 (7)	−0.0038 (6)
C8	0.0415 (7)	0.0427 (6)	0.0534 (8)	0.0024 (6)	0.0011 (6)	−0.0018 (6)
C9	0.0414 (7)	0.0469 (7)	0.0492 (7)	0.0032 (6)	0.0032 (6)	0.0059 (6)
C10	0.0508 (9)	0.0632 (9)	0.0520 (8)	−0.0002 (7)	0.0027 (7)	−0.0012 (7)
C11	0.0663 (11)	0.0764 (11)	0.0541 (9)	0.0055 (9)	0.0177 (8)	−0.0022 (8)
C12	0.0499 (9)	0.0789 (11)	0.0707 (11)	0.0030 (8)	0.0207 (9)	0.0056 (9)
C13	0.0458 (8)	0.0650 (9)	0.0774 (11)	−0.0079 (7)	0.0060 (9)	0.0036 (9)
C14	0.0454 (8)	0.0459 (7)	0.0586 (8)	−0.0005 (6)	0.0026 (7)	0.0066 (6)
C15	0.0578 (9)	0.0578 (9)	0.0800 (12)	−0.0053 (7)	0.0007 (9)	−0.0111 (9)
C16	0.0501 (11)	0.150 (2)	0.0910 (16)	0.0072 (12)	0.0129 (10)	−0.0378 (15)
C17	0.0953 (15)	0.0592 (10)	0.0664 (11)	−0.0078 (9)	−0.0073 (11)	0.0132 (8)

O1—C7	1.2156 (17)	C9—C14	1.400 (2)
N1—C7	1.3401 (17)	C10—C11	1.377 (2)
N1—N2	1.3842 (16)	C10—H10A	0.9300
N1—H1A	0.832 (15)	C11—C12	1.374 (3)
N2—C8	1.2723 (18)	C11—H11A	0.9300
C1—C2	1.378 (2)	C12—C13	1.376 (3)
C1—C6	1.387 (2)	C12—H12A	0.9300
C1—H1B	0.9300	C13—C14	1.384 (2)
C2—C3	1.378 (3)	C13—H13A	0.9300
C2—H2B	0.9300	C14—C15	1.500 (2)
C3—C4	1.384 (3)	C15—H15A	0.9600
C3—C16	1.507 (2)	C15—H15B	0.9600
C4—C5	1.393 (2)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.401 (2)	C16—H16B	0.9600
C5—C17	1.500 (2)	C16—H16C	0.9600
C6—C7	1.4933 (19)	C17—H17A	0.9600
C8—C9	1.4675 (19)	C17—H17B	0.9600
C8—H8A	0.9300	C17—H17C	0.9600
C9—C10	1.392 (2)
C7—N1—N2	120.73 (11)	C11—C10—H10A	119.4
C7—N1—H1A	120.4 (10)	C9—C10—H10A	119.4
N2—N1—H1A	118.9 (10)	C12—C11—C10	119.26 (16)
C8—N2—N1	114.66 (11)	C12—C11—H11A	120.4
C2—C1—C6	121.07 (15)	C10—C11—H11A	120.4
C2—C1—H1B	119.5	C11—C12—C13	120.04 (15)
C6—C1—H1B	119.5	C11—C12—H12A	120.0
C1—C2—C3	120.80 (16)	C13—C12—H12A	120.0
C1—C2—H2B	119.6	C12—C13—C14	122.03 (16)
C3—C2—H2B	119.6	C12—C13—H13A	119.0
C2—C3—C4	117.73 (14)	C14—C13—H13A	119.0
C2—C3—C16	121.07 (18)	C13—C14—C9	117.84 (15)
C4—C3—C16	121.17 (18)	C13—C14—C15	120.58 (15)
C3—C4—C5	123.35 (14)	C9—C14—C15	121.54 (14)
C3—C4—H4A	118.3	C14—C15—H15A	109.5
C5—C4—H4A	118.3	C14—C15—H15B	109.5
C4—C5—C6	117.36 (14)	H15A—C15—H15B	109.5
C4—C5—C17	120.09 (15)	C14—C15—H15C	109.5
C6—C5—C17	122.54 (15)	H15A—C15—H15C	109.5
C1—C6—C5	119.67 (13)	H15B—C15—H15C	109.5
C1—C6—C7	119.13 (13)	C3—C16—H16A	109.5
C5—C6—C7	121.19 (13)	C3—C16—H16B	109.5
O1—C7—N1	122.42 (14)	H16A—C16—H16B	109.5
O1—C7—C6	123.16 (13)	C3—C16—H16C	109.5
N1—C7—C6	114.42 (11)	H16A—C16—H16C	109.5
N2—C8—C9	120.62 (12)	H16B—C16—H16C	109.5
N2—C8—H8A	119.7	C5—C17—H17A	109.5
C9—C8—H8A	119.7	C5—C17—H17B	109.5
C10—C9—C14	119.67 (14)	H17A—C17—H17B	109.5
C10—C9—C8	120.32 (13)	C5—C17—H17C	109.5
C14—C9—C8	120.01 (13)	H17A—C17—H17C	109.5
C11—C10—C9	121.14 (15)	H17B—C17—H17C	109.5
C7—N1—N2—C8	170.77 (14)	C5—C6—C7—O1	−49.4 (2)
C6—C1—C2—C3	−0.8 (2)	C1—C6—C7—N1	−49.99 (18)
C1—C2—C3—C4	1.3 (2)	C5—C6—C7—N1	130.66 (14)
C1—C2—C3—C16	−176.88 (17)	N1—N2—C8—C9	176.93 (12)
C2—C3—C4—C5	−1.2 (2)	N2—C8—C9—C10	−30.9 (2)
C16—C3—C4—C5	177.01 (16)	N2—C8—C9—C14	149.45 (15)
C3—C4—C5—C6	0.5 (2)	C14—C9—C10—C11	−0.6 (2)
C3—C4—C5—C17	−178.19 (16)	C8—C9—C10—C11	179.71 (15)
C2—C1—C6—C5	0.0 (2)	C9—C10—C11—C12	1.2 (3)
C2—C1—C6—C7	−179.36 (14)	C10—C11—C12—C13	−0.9 (3)
C4—C5—C6—C1	0.16 (19)	C11—C12—C13—C14	0.0 (3)
C17—C5—C6—C1	178.77 (14)	C12—C13—C14—C9	0.6 (2)
C4—C5—C6—C7	179.50 (12)	C12—C13—C14—C15	−177.14 (17)
C17—C5—C6—C7	−1.9 (2)	C10—C9—C14—C13	−0.2 (2)
N2—N1—C7—O1	−2.7 (3)	C8—C9—C14—C13	179.43 (14)
N2—N1—C7—C6	177.21 (12)	C10—C9—C14—C15	177.45 (15)
C1—C6—C7—O1	129.9 (2)	C8—C9—C14—C15	−2.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.833 (15)	2.000 (15)	2.8150 (14)	166.1 (14)
C8—H8A···O1i	0.93	2.52	3.2696 (19)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.833 (15)	2.000 (15)	2.8150 (14)	166.1 (14)
C8—H8A⋯O1i	0.93	2.52	3.2696 (19)	138

Symmetry code: (i) .