N'-[4-(Dimethyl-amino)benzyl-idene]benzohydrazide.

In the title mol-ecule, C(16)H(17)N(3)O, the two aromatic rings form a dihedral angle of 4.51 (18)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link mol-ecules related by translation along the a axis into ribbons.

Related literature

For the biological properties of Schiff base ligands, see Bedia et al. (2006 ▶). For related crystal structures, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Nie (2008 ▶).

Experimental

Crystal data

C16H17N3O

M = 267.33

Orthorhombic,

a = 5.131 (3) Å

b = 8.446 (4) Å

c = 32.502 (16) Å

V = 1408.5 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.40 × 0.31 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.988

6499 measured reflections

1489 independent reflections

768 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.066

S = 1.00

1489 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.11 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/S1600536809036460/cv2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036460/cv2609Isup2.hkl

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

C16H17N3O	Dx = 1.261 Mg m−3
Mr = 267.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 731 reflections
a = 5.131 (3) Å	θ = 2.5–19.0°
b = 8.446 (4) Å	µ = 0.08 mm−1
c = 32.502 (16) Å	T = 298 K
V = 1408.5 (13) Å3	Block, red
Z = 4	0.40 × 0.31 × 0.15 mm
F(000) = 568

Bruker SMART APEX CCD area-detector diffractometer	1489 independent reflections
Radiation source: fine-focus sealed tube	768 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
Tmin = 0.968, Tmax = 0.988	k = −10→5
6499 measured reflections	l = −38→37

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2)]
1489 reflections	(Δ/σ)max = 0.045
183 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.11 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
N1	0.8782 (6)	0.6093 (3)	0.16374 (9)	0.0668 (9)
H1	1.0323	0.6000	0.1738	0.080*
N2	0.8356 (6)	0.5902 (4)	0.12192 (9)	0.0661 (9)
N3	1.0131 (7)	0.4725 (4)	−0.07166 (10)	0.0921 (12)
O1	0.4487 (5)	0.6576 (3)	0.17584 (7)	0.0753 (8)
C1	0.6729 (8)	0.6429 (4)	0.18839 (11)	0.0584 (11)
C2	0.7361 (7)	0.6580 (4)	0.23326 (10)	0.0527 (10)
C3	0.9403 (7)	0.5772 (4)	0.25149 (12)	0.0708 (12)
H3	1.0500	0.5149	0.2355	0.085*
C4	0.9818 (8)	0.5887 (5)	0.29326 (12)	0.0841 (13)
H4	1.1166	0.5321	0.3055	0.101*
C5	0.8242 (9)	0.6838 (5)	0.31681 (12)	0.0825 (13)
H5	0.8557	0.6944	0.3448	0.099*
C6	0.6207 (9)	0.7630 (4)	0.29898 (12)	0.0778 (13)
H6	0.5119	0.8259	0.3150	0.093*
C7	0.5770 (8)	0.7494 (4)	0.25716 (12)	0.0696 (12)
H7	0.4379	0.8029	0.2452	0.084*
C8	1.0327 (7)	0.5383 (4)	0.10171 (11)	0.0650 (12)
H8	1.1840	0.5108	0.1157	0.078*
C9	1.0231 (7)	0.5218 (4)	0.05744 (11)	0.0597 (11)
C10	0.8437 (8)	0.5959 (4)	0.03323 (11)	0.0690 (11)
H10	0.7180	0.6588	0.0458	0.083*
C11	0.8400 (9)	0.5818 (4)	−0.00856 (11)	0.0784 (12)
H11	0.7136	0.6358	−0.0235	0.094*
C12	1.0201 (9)	0.4892 (5)	−0.02920 (12)	0.0674 (11)
C13	1.2002 (8)	0.4120 (5)	−0.00492 (13)	0.0843 (13)
H13	1.3229	0.3462	−0.0172	0.101*
C14	1.2020 (7)	0.4303 (5)	0.03710 (12)	0.0813 (14)
H14	1.3297	0.3786	0.0523	0.098*
C15	1.2059 (9)	0.3741 (5)	−0.09163 (11)	0.1262 (19)
H15A	1.2164	0.2740	−0.0777	0.189*
H15B	1.3725	0.4257	−0.0906	0.189*
H15C	1.1568	0.3574	−0.1198	0.189*
C16	0.8855 (10)	0.5890 (4)	−0.09662 (11)	0.1149 (18)
H16A	0.7058	0.5968	−0.0887	0.172*
H16B	0.8963	0.5584	−0.1250	0.172*
H16C	0.9690	0.6897	−0.0929	0.172*

	U11	U22	U33	U12	U13	U23
N1	0.052 (2)	0.097 (2)	0.052 (2)	0.0054 (19)	−0.0077 (19)	0.0059 (18)
N2	0.062 (2)	0.089 (2)	0.047 (2)	−0.001 (2)	−0.0067 (19)	−0.0006 (18)
N3	0.124 (3)	0.094 (3)	0.058 (2)	−0.008 (3)	0.015 (3)	−0.004 (2)
O1	0.0489 (16)	0.110 (2)	0.0666 (17)	0.0048 (17)	−0.0071 (16)	0.0070 (15)
C1	0.052 (3)	0.063 (3)	0.060 (3)	−0.001 (3)	0.000 (3)	0.004 (2)
C2	0.051 (3)	0.060 (3)	0.047 (2)	−0.004 (2)	0.001 (2)	0.001 (2)
C3	0.053 (3)	0.097 (3)	0.063 (3)	0.013 (2)	0.001 (2)	0.012 (2)
C4	0.074 (3)	0.117 (4)	0.062 (3)	0.008 (3)	−0.015 (3)	0.006 (3)
C5	0.086 (3)	0.104 (4)	0.058 (3)	−0.010 (3)	0.002 (3)	0.000 (3)
C6	0.086 (4)	0.082 (3)	0.066 (3)	0.012 (3)	0.007 (3)	−0.007 (2)
C7	0.072 (3)	0.068 (3)	0.069 (3)	0.015 (3)	0.003 (3)	0.005 (2)
C8	0.055 (3)	0.083 (3)	0.057 (3)	0.010 (3)	−0.003 (2)	0.005 (2)
C9	0.053 (3)	0.079 (3)	0.047 (2)	0.003 (3)	0.005 (2)	0.005 (2)
C10	0.070 (3)	0.075 (3)	0.062 (3)	0.015 (3)	0.004 (3)	−0.004 (2)
C11	0.091 (3)	0.089 (3)	0.056 (3)	0.009 (3)	−0.006 (3)	0.007 (2)
C12	0.078 (3)	0.069 (3)	0.056 (3)	−0.006 (3)	0.012 (3)	0.005 (2)
C13	0.081 (3)	0.097 (3)	0.075 (3)	0.021 (3)	0.020 (3)	−0.002 (3)
C14	0.067 (3)	0.111 (4)	0.066 (3)	0.032 (3)	0.002 (3)	0.006 (3)
C15	0.112 (4)	0.196 (5)	0.071 (3)	−0.019 (4)	0.028 (3)	−0.033 (3)
C16	0.180 (5)	0.099 (4)	0.066 (3)	−0.018 (4)	−0.021 (3)	0.014 (3)

N1—C1	1.353 (4)	C7—H7	0.9300
N1—N2	1.386 (3)	C8—C9	1.446 (4)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.283 (4)	C9—C10	1.363 (4)
N3—C12	1.388 (4)	C9—C14	1.370 (4)
N3—C16	1.433 (4)	C10—C11	1.363 (4)
N3—C15	1.446 (4)	C10—H10	0.9300
O1—C1	1.227 (4)	C11—C12	1.384 (5)
C1—C2	1.499 (4)	C11—H11	0.9300
C2—C7	1.366 (4)	C12—C13	1.379 (4)
C2—C3	1.384 (4)	C13—C14	1.374 (4)
C3—C4	1.378 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.369 (5)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.382 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C1—N1—N2	118.8 (3)	C10—C9—C14	115.6 (4)
C1—N1—H1	120.6	C10—C9—C8	123.6 (4)
N2—N1—H1	120.6	C14—C9—C8	120.8 (4)
C8—N2—N1	114.7 (3)	C11—C10—C9	123.0 (4)
C12—N3—C16	120.3 (4)	C11—C10—H10	118.5
C12—N3—C15	119.2 (4)	C9—C10—H10	118.5
C16—N3—C15	116.9 (4)	C10—C11—C12	121.5 (4)
O1—C1—N1	123.7 (3)	C10—C11—H11	119.2
O1—C1—C2	121.1 (4)	C12—C11—H11	119.2
N1—C1—C2	115.2 (3)	C11—C12—C13	115.9 (4)
C7—C2—C3	119.2 (3)	C11—C12—N3	121.5 (4)
C7—C2—C1	118.2 (4)	C13—C12—N3	122.5 (4)
C3—C2—C1	122.6 (4)	C14—C13—C12	121.3 (4)
C4—C3—C2	120.3 (4)	C14—C13—H13	119.4
C4—C3—H3	119.9	C12—C13—H13	119.4
C2—C3—H3	119.9	C9—C14—C13	122.6 (4)
C5—C4—C3	120.0 (4)	C9—C14—H14	118.7
C5—C4—H4	120.0	C13—C14—H14	118.7
C3—C4—H4	120.0	N3—C15—H15A	109.5
C6—C5—C4	120.0 (4)	N3—C15—H15B	109.5
C6—C5—H5	120.0	H15A—C15—H15B	109.5
C4—C5—H5	120.0	N3—C15—H15C	109.5
C5—C6—C7	120.0 (4)	H15A—C15—H15C	109.5
C5—C6—H6	120.0	H15B—C15—H15C	109.5
C7—C6—H6	120.0	N3—C16—H16A	109.5
C2—C7—C6	120.6 (4)	N3—C16—H16B	109.5
C2—C7—H7	119.7	H16A—C16—H16B	109.5
C6—C7—H7	119.7	N3—C16—H16C	109.5
N2—C8—C9	121.0 (4)	H16A—C16—H16C	109.5
N2—C8—H8	119.5	H16B—C16—H16C	109.5
C9—C8—H8	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.19	2.982 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.19	2.982 (4)	153

Symmetry code: (i) .