N-(2-Eth-oxy-phen-yl)formamide.

The title compound, C(9)H(11)NO(2), was obtained as an unexpected product in an attempt to synthesize a triazene ligand. The title mol-ecule is almost planar, with the formamide and eth-oxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean plane of the benzene ring. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming a chain along the a axis. Weak C-H⋯π inter-actions with an H⋯π distance of 2.78 Å reinforce the crystal packing, resulting in a three-dimensional network.

Related literature

For preparation of several trizene compounds in our laboratory, see: Melardi et al. (2011 ▶). For similar crystal structures, see: Landman et al. (2011 ▶); Chitanda et al. (2008 ▶); Hu et al. (2010 ▶).

Experimental

Crystal data

C9H11NO2

M = 165.19

Orthorhombic,

a = 7.9079 (4) Å

b = 14.1253 (6) Å

c = 15.9555 (7) Å

V = 1782.25 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.45 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007) ▶ T min = 0.671, T max = 0.746

8725 measured reflections

1961 independent reflections

1248 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.03

1961 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XPW in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200205X/pv2505sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200205X/pv2505Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200205X/pv2505Isup3.cml

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

C9H11NO2	F(000) = 704
Mr = 165.19	Dx = 1.231 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2150 reflections
a = 7.9079 (4) Å	θ = 2.6–23.1°
b = 14.1253 (6) Å	µ = 0.09 mm−1
c = 15.9555 (7) Å	T = 296 K
V = 1782.25 (14) Å3	Cubic, colourless
Z = 8	0.45 × 0.23 × 0.18 mm

Bruker APEXII CCD diffractometer	1961 independent reflections
Radiation source: fine-focus sealed tube	1248 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.1°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.671, Tmax = 0.746	k = −18→17
8725 measured reflections	l = −20→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.278P] where P = (Fo2 + 2Fc2)/3
1961 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.14029 (12)	0.40133 (8)	0.12756 (7)	0.0571 (3)
N1	−0.12270 (15)	0.33831 (10)	0.04588 (8)	0.0525 (4)
H1	−0.0300	0.3086	0.0561	0.063*
O2	−0.37570 (15)	0.31796 (10)	−0.02102 (9)	0.0808 (4)
C1	0.3874 (2)	0.33886 (16)	0.18902 (13)	0.0842 (7)
H1A	0.3183	0.2875	0.2085	0.126*
H1B	0.4759	0.3507	0.2288	0.126*
H1C	0.4361	0.3226	0.1358	0.126*
C2	0.2815 (2)	0.42535 (14)	0.17963 (11)	0.0653 (5)
H2A	0.2425	0.4468	0.2340	0.078*
H2B	0.3469	0.4758	0.1540	0.078*
C3	0.00875 (19)	0.46374 (11)	0.12280 (10)	0.0489 (4)
C4	−0.13409 (18)	0.43045 (11)	0.07964 (9)	0.0466 (4)
C5	−0.23581 (19)	0.29108 (14)	0.00042 (10)	0.0597 (5)
H5	−0.2045	0.2307	−0.0170	0.072*
C6	−0.2759 (2)	0.48701 (12)	0.07355 (11)	0.0585 (5)
H6	−0.3704	0.4656	0.0446	0.070*
C7	−0.2773 (2)	0.57530 (14)	0.11042 (14)	0.0732 (6)
H7	−0.3740	0.6126	0.1075	0.088*
C8	−0.1370 (3)	0.60824 (13)	0.15134 (14)	0.0784 (6)
H8	−0.1384	0.6683	0.1751	0.094*
C9	0.0067 (2)	0.55295 (13)	0.15765 (12)	0.0661 (5)
H9	0.1017	0.5759	0.1853	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0371 (6)	0.0752 (8)	0.0591 (7)	0.0031 (5)	−0.0080 (5)	−0.0113 (5)
N1	0.0351 (6)	0.0705 (9)	0.0520 (8)	0.0038 (6)	−0.0041 (6)	−0.0075 (7)
O2	0.0456 (7)	0.0982 (10)	0.0987 (10)	0.0009 (7)	−0.0234 (6)	−0.0143 (8)
C1	0.0558 (11)	0.1186 (17)	0.0781 (13)	0.0172 (11)	−0.0227 (10)	−0.0244 (12)
C2	0.0391 (8)	0.0894 (13)	0.0675 (11)	−0.0060 (9)	−0.0073 (8)	−0.0142 (10)
C3	0.0410 (8)	0.0582 (9)	0.0476 (9)	−0.0031 (7)	0.0054 (7)	0.0057 (7)
C4	0.0390 (7)	0.0587 (10)	0.0421 (8)	−0.0028 (7)	0.0041 (6)	0.0076 (7)
C5	0.0450 (9)	0.0784 (12)	0.0556 (10)	−0.0038 (9)	−0.0016 (8)	−0.0094 (8)
C6	0.0457 (9)	0.0660 (11)	0.0638 (10)	0.0035 (8)	−0.0006 (8)	0.0135 (9)
C7	0.0614 (12)	0.0597 (11)	0.0984 (15)	0.0127 (10)	0.0058 (11)	0.0182 (10)
C8	0.0793 (14)	0.0480 (11)	0.1079 (17)	−0.0010 (10)	0.0074 (12)	0.0047 (10)
C9	0.0584 (11)	0.0632 (11)	0.0768 (13)	−0.0131 (9)	0.0000 (9)	0.0013 (9)

O1—C3	1.3656 (18)	C3—C9	1.377 (2)
O1—C2	1.4328 (18)	C3—C4	1.404 (2)
N1—C5	1.331 (2)	C4—C6	1.380 (2)
N1—C4	1.411 (2)	C5—H5	0.9300
N1—H1	0.8600	C6—C7	1.379 (3)
O2—C5	1.2185 (19)	C6—H6	0.9300
C1—C2	1.488 (3)	C7—C8	1.369 (3)
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—C9	1.383 (3)
C1—H1C	0.9600	C8—H8	0.9300
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700
C3—O1—C2	118.24 (12)	C6—C4—C3	119.61 (15)
C5—N1—C4	128.85 (14)	C6—C4—N1	123.97 (14)
C5—N1—H1	115.6	C3—C4—N1	116.40 (13)
C4—N1—H1	115.6	O2—C5—N1	127.37 (18)
C2—C1—H1A	109.5	O2—C5—H5	116.3
C2—C1—H1B	109.5	N1—C5—H5	116.3
H1A—C1—H1B	109.5	C7—C6—C4	120.02 (17)
C2—C1—H1C	109.5	C7—C6—H6	120.0
H1A—C1—H1C	109.5	C4—C6—H6	120.0
H1B—C1—H1C	109.5	C8—C7—C6	120.28 (18)
O1—C2—C1	107.60 (14)	C8—C7—H7	119.9
O1—C2—H2A	110.2	C6—C7—H7	119.9
C1—C2—H2A	110.2	C7—C8—C9	120.60 (18)
O1—C2—H2B	110.2	C7—C8—H8	119.7
C1—C2—H2B	110.2	C9—C8—H8	119.7
H2A—C2—H2B	108.5	C3—C9—C8	119.78 (17)
O1—C3—C9	125.23 (15)	C3—C9—H9	120.1
O1—C3—C4	115.08 (14)	C8—C9—H9	120.1
C9—C3—C4	119.68 (15)
C3—O1—C2—C1	167.77 (15)	C4—N1—C5—O2	−0.8 (3)
C2—O1—C3—C9	6.7 (2)	C3—C4—C6—C7	−0.6 (2)
C2—O1—C3—C4	−172.08 (14)	N1—C4—C6—C7	178.25 (15)
O1—C3—C4—C6	178.00 (13)	C4—C6—C7—C8	1.7 (3)
C9—C3—C4—C6	−0.8 (2)	C6—C7—C8—C9	−1.2 (3)
O1—C3—C4—N1	−0.97 (19)	O1—C3—C9—C8	−177.42 (16)
C9—C3—C4—N1	−179.82 (14)	C4—C3—C9—C8	1.3 (3)
C5—N1—C4—C6	3.4 (3)	C7—C8—C9—C3	−0.3 (3)
C5—N1—C4—C3	−177.67 (15)

Cg is the centroid of the C3–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.20	2.6108 (16)	109.
N1—H1···O2i	0.86	2.24	2.9741 (18)	144.
C2—H2A···Cgii	0.97	2.78	3.5853 (19)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.24	2.9741 (18)	144
C2—H2A⋯Cgii	0.97	2.78	3.5853 (19)	141

Symmetry codes: (i) ; (ii) .