4-Eth-oxy-benzohydrazide.

The title compound, C(9)H(12)N(2)O(2), is approximately planar (r.m.s. deviation = 0.13 Å for all non-H atoms). The carbonyl O atom is involved as acceptor in three different hydrogen-bond inter-actions. One N-H⋯O and the C-H⋯O(carbonyl) contact together with a weak C-H⋯O(eth-oxy) interaction link the mol-ecules into sheets parallel to (102). These are further linked into a three-dimensional network via the remaining C-H⋯O(carbon-yl) hydrogen bond and a C(methyl-ene)-H⋯π inter-action.

Related literature

For the meth­oxy analogue of the title compound, see: Ashiq et al. (2009 ▶). For biological properties of hydrazides, see: Gohil et al. (2010 ▶); Bordoloi et al. (2009 ▶); Kumar et al. (2009 ▶). For the use of hydrazides as precursors for the syntheses of heterocyclic compounds, see: Akhtar et al. (2010 ▶); Akhtar, Hameed, Al-Masoudi et al. (2008 ▶); Akhtar, Hameed, Khan et al. (2008 ▶); Khan, Akhtar et al. (2010 ▶); Khan, Hameed et al. (2010 ▶); Serwar et al. (2009 ▶); Syed et al. (2011 ▶); Zahid et al. (2009 ▶); Zia et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶); For details of the preparation, see: Furniss et al. (1989 ▶).

Experimental

Crystal data

C9H12N2O2

M = 180.21

Monoclinic,

a = 10.8848 (3) Å

b = 10.0453 (2) Å

c = 8.4420 (3) Å

β = 110.669 (4)°

V = 863.64 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

42766 measured reflections

2874 independent reflections

2478 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.106

S = 1.10

2874 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038998/lr2080sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038998/lr2080Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038998/lr2080Isup3.cml

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

C9H12N2O2	F(000) = 384
Mr = 180.21	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Melting point: 403 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8848 (3) Å	Cell parameters from 23790 reflections
b = 10.0453 (2) Å	θ = 2.6–32.6°
c = 8.4420 (3) Å	µ = 0.10 mm−1
β = 110.669 (4)°	T = 100 K
V = 863.64 (4) Å3	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Oxford Diffraction Xcalibur Eos diffractometer	2478 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.024
Graphite monochromator	θmax = 31.5°, θmin = 2.9°
Detector resolution: 16.1419 pixels mm-1	h = −15→15
ω scan	k = −14→14
42766 measured reflections	l = −12→12
2874 independent 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0734P)2 + 0.0351P] where P = (Fo2 + 2Fc2)/3
2874 reflections	(Δ/σ)max = 0.002
131 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.22 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.Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)3.5814 (0.0029) x - 0.3102 (0.0031) y + 6.4744 (0.0016) z = 4.7086 (0.0021)* 0.0107 (0.0005) C1 * -0.0025 (0.0005) C2 * -0.0096 (0.0005) C3 * 0.0135 (0.0005) C4 * -0.0052 (0.0005) C5 * -0.0070 (0.0005) C6 0.1090 (0.0011) C7 0.1528 (0.0013) C8 0.3370 (0.0017) C9 0.4145 (0.0012) O1 0.0757 (0.0010) O2 - 0.0498 (0.0016) N1 - 0.1309 (0.0013) N2Rms deviation of fitted atoms = 0.00893.5873 (0.0049) x + 2.2383 (0.0045) y + 6.2646 (0.0032) z = 6.0909 (0.0020)Angle to previous plane (with approximate e.s.d.) = 14.65 (0.06)* 0.0002 (0.0004) C7 * -0.0001 (0.0002) O1 * 0.0001 (0.0002) N1 * -0.0002 (0.0004) N2Rms deviation of fitted atoms = 0.0001

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	0.14875 (7)	0.60114 (7)	0.67544 (8)	0.01178 (14)
C2	0.21991 (7)	0.50128 (7)	0.62925 (9)	0.01315 (14)
H2	0.1982	0.4104	0.6363	0.016*
C3	0.32166 (7)	0.53422 (7)	0.57344 (9)	0.01377 (14)
H3	0.3685	0.4660	0.5411	0.017*
C4	0.35534 (7)	0.66779 (7)	0.56479 (9)	0.01238 (14)
C5	0.28323 (7)	0.76797 (7)	0.60658 (9)	0.01476 (15)
H5	0.3040	0.8589	0.5977	0.018*
C6	0.18082 (7)	0.73392 (7)	0.66132 (9)	0.01406 (15)
H6	0.1319	0.8023	0.6896	0.017*
C7	0.04616 (7)	0.56096 (7)	0.74544 (9)	0.01238 (14)
C8	0.50091 (7)	0.82661 (7)	0.51338 (10)	0.01446 (15)
H8A	0.5170	0.8694	0.6245	0.017*
H8B	0.4315	0.8771	0.4259	0.017*
C9	0.62551 (8)	0.82519 (8)	0.47285 (10)	0.01797 (16)
H9A	0.6925	0.7725	0.5582	0.027*
H9B	0.6572	0.9165	0.4733	0.027*
H9C	0.6076	0.7856	0.3608	0.027*
N1	−0.13631 (7)	0.63025 (7)	0.82516 (9)	0.01874 (15)
H01	−0.0919 (13)	0.6029 (13)	0.9364 (17)	0.039 (3)*
H02	−0.1806 (12)	0.5584 (13)	0.7605 (16)	0.033 (3)*
N2	−0.03653 (6)	0.65623 (6)	0.75869 (8)	0.01518 (14)
H03	−0.0305 (11)	0.7382 (13)	0.7308 (14)	0.026 (3)*
O1	0.03801 (5)	0.44481 (5)	0.79156 (7)	0.01735 (13)
O2	0.46083 (5)	0.69025 (5)	0.51711 (7)	0.01480 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0120 (3)	0.0097 (3)	0.0148 (3)	0.0001 (2)	0.0061 (2)	0.0006 (2)
C2	0.0147 (3)	0.0096 (3)	0.0165 (3)	−0.0004 (2)	0.0072 (2)	−0.0006 (2)
C3	0.0156 (3)	0.0104 (3)	0.0175 (3)	0.0008 (2)	0.0086 (3)	−0.0006 (2)
C4	0.0129 (3)	0.0112 (3)	0.0149 (3)	0.0005 (2)	0.0073 (2)	0.0006 (2)
C5	0.0167 (3)	0.0095 (3)	0.0216 (3)	0.0006 (2)	0.0112 (3)	0.0012 (2)
C6	0.0151 (3)	0.0103 (3)	0.0198 (3)	0.0012 (2)	0.0100 (3)	0.0008 (2)
C7	0.0122 (3)	0.0109 (3)	0.0147 (3)	−0.0008 (2)	0.0057 (2)	−0.0002 (2)
C8	0.0163 (3)	0.0102 (3)	0.0197 (3)	−0.0009 (2)	0.0099 (3)	0.0001 (2)
C9	0.0170 (3)	0.0150 (3)	0.0261 (4)	−0.0019 (2)	0.0128 (3)	−0.0007 (3)
N1	0.0168 (3)	0.0200 (3)	0.0247 (3)	0.0005 (2)	0.0139 (3)	0.0032 (3)
N2	0.0152 (3)	0.0117 (3)	0.0232 (3)	0.0008 (2)	0.0125 (2)	0.0025 (2)
O1	0.0196 (3)	0.0106 (3)	0.0260 (3)	0.00006 (19)	0.0133 (2)	0.0031 (2)
O2	0.0159 (3)	0.0105 (2)	0.0229 (3)	−0.00056 (18)	0.0128 (2)	0.00054 (19)

C1—C6	1.3944 (10)	C2—H2	0.9500
C1—C2	1.4041 (10)	C3—H3	0.9500
C1—C7	1.4916 (10)	C5—H5	0.9500
C2—C3	1.3879 (10)	C6—H6	0.9500
C3—C4	1.3997 (10)	C8—H8A	0.9900
C4—O2	1.3630 (8)	C8—H8B	0.9900
C4—C5	1.3959 (10)	C9—H9A	0.9800
C5—C6	1.3917 (10)	C9—H9B	0.9800
C7—O1	1.2431 (8)	C9—H9C	0.9800
C7—N2	1.3452 (9)	N1—H01	0.933 (13)
C8—O2	1.4413 (9)	N1—H02	0.931 (13)
C8—C9	1.5114 (10)	N2—H03	0.865 (13)
N1—N2	1.4117 (9)
C6—C1—C2	118.70 (6)	C6—C5—H5	120.2
C6—C1—C7	122.53 (6)	C4—C5—H5	120.2
C2—C1—C7	118.70 (6)	C5—C6—H6	119.4
C3—C2—C1	120.56 (6)	C1—C6—H6	119.4
C2—C3—C4	120.09 (6)	O2—C8—H8A	110.2
O2—C4—C5	124.25 (6)	C9—C8—H8A	110.2
O2—C4—C3	115.95 (6)	O2—C8—H8B	110.2
C5—C4—C3	119.79 (6)	C9—C8—H8B	110.2
C6—C5—C4	119.63 (7)	H8A—C8—H8B	108.5
C5—C6—C1	121.17 (6)	C8—C9—H9A	109.5
O1—C7—N2	121.19 (6)	C8—C9—H9B	109.5
O1—C7—C1	121.62 (6)	H9A—C9—H9B	109.5
N2—C7—C1	117.19 (6)	C8—C9—H9C	109.5
O2—C8—C9	107.38 (6)	H9A—C9—H9C	109.5
C7—N2—N1	122.19 (6)	H9B—C9—H9C	109.5
C4—O2—C8	117.18 (5)	N2—N1—H01	104.9 (8)
C3—C2—H2	119.7	N2—N1—H02	102.9 (7)
C1—C2—H2	119.7	H01—N1—H02	109.8 (11)
C2—C3—H3	120.0	C7—N2—H03	122.5 (8)
C4—C3—H3	120.0	N1—N2—H03	115.3 (8)
C6—C1—C2—C3	1.10 (10)	C6—C1—C7—O1	−164.06 (7)
C7—C1—C2—C3	−176.01 (6)	C2—C1—C7—O1	12.93 (10)
C1—C2—C3—C4	0.82 (11)	C6—C1—C7—N2	15.13 (10)
C2—C3—C4—O2	176.66 (6)	C2—C1—C7—N2	−167.88 (6)
C2—C3—C4—C5	−2.32 (11)	O1—C7—N2—N1	0.05 (11)
O2—C4—C5—C6	−177.01 (6)	C1—C7—N2—N1	−179.15 (6)
C3—C4—C5—C6	1.89 (11)	C5—C4—O2—C8	1.26 (10)
C4—C5—C6—C1	0.05 (11)	C3—C4—O2—C8	−177.68 (6)
C2—C1—C6—C5	−1.54 (11)	C9—C8—O2—C4	174.98 (6)
C7—C1—C6—C5	175.46 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H03···O1i	0.865 (13)	2.083 (13)	2.9290 (9)	165.6 (11)
C6—H6···O1i	0.95	2.39	3.3149 (9)	165
C3—H3···O2ii	0.95	2.61	3.5428 (9)	168
N1—H01···O1iii	0.933 (13)	2.212 (14)	3.1207 (9)	164.1 (12)
C8—H8B···Cgiv	0.99	2.65	3.499 (1)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H03⋯O1i	0.865 (13)	2.083 (13)	2.9290 (9)	165.6 (11)
C6—H6⋯O1i	0.95	2.39	3.3149 (9)	165
C3—H3⋯O2ii	0.95	2.61	3.5428 (9)	168
N1—H01⋯O1iii	0.933 (13)	2.212 (14)	3.1207 (9)	164.1 (12)
C8—H8B⋯Cg iv	0.99	2.65	3.499 (1)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .