(E)-3-(3,5-Dimethoxy-phen-yl)acrylo-hydrazide.

In the title compound, C(11)H(14)N(2)O(3), the planar hydrazide group is oriented with respect to the benzene ring at a dihedral angle of 48.00 (3)°. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For related literature, see: Zheng et al. (2003 ▶); Al-Talib et al. (1990 ▶); Yousif et al. (1986 ▶); Ahmad et al. (2001 ▶); Al-Soud et al. (2004 ▶); El-Emam et al. (2004 ▶); Furniss et al. (1978 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H14N2O3

M = 222.24

Monoclinic,

a = 4.8910 (19) Å

b = 30.358 (11) Å

c = 8.3440 (14) Å

β = 113.02 (3)°

V = 1140.4 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 (1) K

0.90 × 0.17 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: gaussian (Coppens, 1970 ▶) T min = 0.961, T max = 0.993

7864 measured reflections

2522 independent reflections

1547 reflections with I > 2σ(I)

R int = 0.139

Refinement

R[F 2 > 2σ(F 2)] = 0.111

wR(F 2) = 0.274

S = 1.13

2522 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EvalCCD (Duisenberg, 1992 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808028985/hk2530sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028985/hk2530Isup2.hkl

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

C11H14N2O3	F(000) = 472
Mr = 222.24	Dx = 1.294 Mg m−3
Monoclinic, P21/c	Melting point: 401(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.8910 (19) Å	Cell parameters from 7914 reflections
b = 30.358 (11) Å	θ = 1–27.5°
c = 8.3440 (14) Å	µ = 0.10 mm−1
β = 113.02 (3)°	T = 150 K
V = 1140.4 (7) Å3	Needle, colorless
Z = 4	0.90 × 0.17 × 0.12 mm

Bruker–Nonius KappaCCD area-detector diffractometer	2522 independent reflections
Radiation source: fine-focus sealed tube	1547 reflections with I > 2σ(I)
graphite	Rint = 0.139
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −5→6
Absorption correction: gaussian (Coppens, 1970)	k = −39→35
Tmin = 0.961, Tmax = 0.993	l = −10→9
7864 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)] = 0.111	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.274	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0574P)2 + 2.6221P] where P = (Fo2 + 2Fc2)/3
2522 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.41 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
O1	0.5287 (7)	0.28398 (13)	0.5987 (6)	0.0682 (12)
O2	−0.4491 (7)	0.08832 (12)	0.3236 (4)	0.0538 (9)
O3	0.3626 (7)	0.04751 (12)	0.8379 (5)	0.0544 (10)
N1	0.0720 (8)	0.30545 (13)	0.5611 (6)	0.0468 (10)
H1	−0.0993	0.2975	0.5571	0.056*
N2	0.1165 (9)	0.34981 (14)	0.5371 (6)	0.0548 (11)
H2A	0.2856	0.3587	0.5404	0.066*
H2B	−0.0256	0.3683	0.5186	0.066*
C1	0.2785 (10)	0.27498 (16)	0.5905 (7)	0.0469 (12)
C2	0.1853 (14)	0.22916 (18)	0.6146 (10)	0.074 (2)
H2	0.0374	0.2236	0.6559	0.089*
C3	0.3475 (11)	0.19327 (16)	0.5674 (7)	0.0516 (13)
H3	0.5095	0.1979	0.5373	0.062*
C4	0.2192 (10)	0.14822 (15)	0.5752 (6)	0.0437 (11)
C5	−0.0544 (10)	0.13674 (16)	0.4480 (6)	0.0451 (11)
H5	−0.1530	0.1561	0.3573	0.054*
C6	−0.1797 (9)	0.09645 (15)	0.4560 (6)	0.0408 (10)
C7	−0.0380 (9)	0.06710 (16)	0.5864 (6)	0.0417 (10)
H7	−0.1233	0.0400	0.5912	0.050*
C8	0.2389 (10)	0.07918 (15)	0.7127 (6)	0.0404 (10)
C9	0.3672 (9)	0.11891 (15)	0.7090 (6)	0.0391 (10)
H9	0.5512	0.1261	0.7945	0.047*
C10	−0.5868 (11)	0.0472 (2)	0.3233 (7)	0.0605 (15)
H10A	−0.4515	0.0237	0.3308	0.073*
H10B	−0.7611	0.0443	0.2179	0.073*
H10C	−0.6420	0.0461	0.4217	0.073*
C11	0.6609 (10)	0.05504 (18)	0.9613 (7)	0.0547 (13)
H11A	0.7879	0.0602	0.8999	0.066*
H11B	0.7292	0.0296	1.0344	0.066*
H11C	0.6652	0.0802	1.0318	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0387 (18)	0.061 (2)	0.117 (4)	−0.0048 (17)	0.043 (2)	0.001 (2)
O2	0.0457 (18)	0.065 (2)	0.0394 (19)	−0.0032 (17)	0.0038 (15)	−0.0008 (16)
O3	0.0441 (18)	0.056 (2)	0.049 (2)	−0.0058 (16)	0.0027 (15)	0.0103 (16)
N1	0.0296 (18)	0.050 (2)	0.062 (3)	−0.0042 (17)	0.0198 (18)	−0.005 (2)
N2	0.043 (2)	0.049 (2)	0.072 (3)	0.0035 (19)	0.022 (2)	0.009 (2)
C1	0.040 (2)	0.050 (3)	0.056 (3)	−0.005 (2)	0.024 (2)	−0.003 (2)
C2	0.076 (4)	0.048 (3)	0.134 (6)	−0.010 (3)	0.080 (4)	−0.008 (3)
C3	0.048 (3)	0.046 (3)	0.069 (4)	0.000 (2)	0.032 (3)	0.006 (2)
C4	0.043 (2)	0.047 (3)	0.049 (3)	−0.003 (2)	0.026 (2)	−0.004 (2)
C5	0.048 (3)	0.051 (3)	0.035 (2)	0.008 (2)	0.015 (2)	0.008 (2)
C6	0.038 (2)	0.049 (3)	0.037 (2)	0.002 (2)	0.0157 (19)	−0.006 (2)
C7	0.040 (2)	0.043 (2)	0.043 (3)	−0.005 (2)	0.017 (2)	−0.004 (2)
C8	0.042 (2)	0.045 (3)	0.035 (2)	0.003 (2)	0.0155 (19)	0.0017 (19)
C9	0.033 (2)	0.045 (3)	0.038 (2)	−0.0019 (19)	0.0119 (18)	−0.0043 (19)
C10	0.043 (3)	0.078 (4)	0.049 (3)	−0.008 (3)	0.006 (2)	−0.009 (3)
C11	0.046 (3)	0.064 (3)	0.045 (3)	−0.003 (2)	0.007 (2)	0.006 (2)

O1—C1	1.230 (5)	C4—C5	1.389 (7)
O2—C6	1.371 (5)	C5—H5	0.9301
O2—C10	1.416 (6)	C6—C5	1.381 (7)
O3—C8	1.374 (5)	C6—C7	1.367 (7)
O3—C11	1.438 (6)	C7—H7	0.9298
N1—N2	1.391 (6)	C8—C7	1.402 (6)
N1—C1	1.320 (6)	C8—C9	1.365 (6)
N1—H1	0.8600	C9—C4	1.389 (7)
N2—H2A	0.8601	C9—H9	0.9300
N2—H2B	0.8600	C10—H10A	0.9598
C1—C2	1.502 (7)	C10—H10B	0.9600
C2—H2	0.9300	C10—H10C	0.9600
C3—C2	1.489 (7)	C11—H11A	0.9601
C3—C4	1.517 (7)	C11—H11B	0.9600
C3—H3	0.9300	C11—H11C	0.9600
N2—N1—H1	118.2	C7—C6—C5	121.3 (4)
C1—N1—N2	123.6 (4)	O2—C6—C5	115.2 (4)
C1—N1—H1	118.2	C6—C7—C8	117.9 (4)
N1—N2—H2A	120.1	C6—C7—H7	120.9
N1—N2—H2B	119.9	C8—C7—H7	121.1
H2A—N2—H2B	120.0	C9—C8—O3	124.4 (4)
C6—O2—C10	117.8 (4)	C9—C8—C7	122.1 (4)
C8—O3—C11	117.1 (4)	O3—C8—C7	113.4 (4)
O1—C1—N1	121.8 (5)	C8—C9—C4	119.0 (4)
O1—C1—C2	123.1 (5)	C8—C9—H9	120.4
N1—C1—C2	115.1 (4)	C4—C9—H9	120.6
C1—C2—H2	122.6	O2—C10—H10A	109.9
C3—C2—C1	114.9 (4)	O2—C10—H10B	109.6
C3—C2—H2	122.5	O2—C10—H10C	108.9
C2—C3—C4	112.1 (4)	H10A—C10—H10B	109.5
C2—C3—H3	124.0	H10A—C10—H10C	109.5
C4—C3—H3	123.9	H10B—C10—H10C	109.5
C5—C4—C3	119.0 (4)	O3—C11—H11A	109.3
C5—C4—C9	119.8 (4)	O3—C11—H11B	109.3
C9—C4—C3	121.2 (4)	O3—C11—H11C	109.8
C4—C5—H5	120.1	H11A—C11—H11B	109.5
C6—C5—C4	119.9 (4)	H11A—C11—H11C	109.5
C6—C5—H5	120.0	H11B—C11—H11C	109.5
C7—C6—O2	123.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.870 (3)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.870 (3)	168

Symmetry code: (i) .