Ethyl 3-benzyl-idenecarbazate.

In the title compound, C(10)H(12)N(2)O(2), the dihedral angle between the mean planes of the aromatic ring and the side chain (r.m.s. deviation = 0.035 Å) is 18.23 (13)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating C(4) amide chains propagating in [010].

Related literature

For related structures, see: Li & Jian (2010 ▶); Li & Meng (2010 ▶).

Experimental

Crystal data

C10H12N2O2

M = 192.22

Orthorhombic,

a = 11.309 (2) Å

b = 7.6693 (15) Å

c = 24.684 (5) Å

V = 2140.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

19439 measured reflections

2449 independent reflections

1147 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.206

S = 1.00

2449 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 global, I. DOI: 10.1107/S1600536810048865/hb5754sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048865/hb5754Isup2.hkl

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

C10H12N2O2	Dx = 1.193 Mg m−3
Mr = 192.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2449 reflections
a = 11.309 (2) Å	θ = 3.3–27.5°
b = 7.6693 (15) Å	µ = 0.09 mm−1
c = 24.684 (5) Å	T = 293 K
V = 2140.8 (7) Å3	Block, colorless
Z = 8	0.22 × 0.20 × 0.18 mm
F(000) = 816

Bruker SMART CCD diffractometer	1147 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.100
graphite	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −14→14
19439 measured reflections	k = −9→8
2449 independent reflections	l = −32→31

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1041P)2] where P = (Fo2 + 2Fc2)/3
2449 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.20 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.

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
N2	0.26886 (18)	0.1974 (3)	0.64212 (7)	0.0581 (6)
C5	0.3635 (2)	0.2155 (3)	0.72854 (9)	0.0531 (6)
N1	0.2584 (2)	0.2687 (3)	0.59115 (7)	0.0683 (6)
H1A	0.3045	0.3519	0.5811	0.082*
C3	0.1754 (3)	0.2069 (4)	0.55722 (10)	0.0662 (7)
O2	0.11238 (17)	0.0819 (2)	0.56498 (7)	0.0752 (6)
C4	0.3463 (2)	0.2693 (3)	0.67226 (9)	0.0591 (7)
H4A	0.3930	0.3582	0.6581	0.071*
C6	0.4598 (2)	0.2798 (4)	0.75763 (10)	0.0663 (7)
H6A	0.5139	0.3528	0.7406	0.080*
O1	0.1713 (2)	0.3068 (3)	0.51302 (7)	0.0940 (7)
C10	0.2827 (2)	0.1092 (3)	0.75513 (9)	0.0591 (7)
H10A	0.2171	0.0668	0.7366	0.071*
C8	0.3955 (3)	0.1299 (4)	0.83678 (10)	0.0730 (8)
H8A	0.4062	0.1007	0.8730	0.088*
C9	0.2993 (2)	0.0663 (3)	0.80883 (10)	0.0689 (8)
H9A	0.2453	−0.0059	0.8263	0.083*
C7	0.4757 (2)	0.2363 (4)	0.81131 (11)	0.0751 (8)
H7A	0.5407	0.2790	0.8302	0.090*
C2	0.0890 (4)	0.2517 (5)	0.47098 (14)	0.1325 (16)
H2B	0.1114	0.1378	0.4573	0.159*
H2C	0.0097	0.2435	0.4858	0.159*
C1	0.0915 (5)	0.3756 (8)	0.42843 (15)	0.167 (2)
H1B	0.0372	0.3408	0.4005	0.250*
H1C	0.1699	0.3820	0.4137	0.250*
H1D	0.0689	0.4878	0.4422	0.250*

	U11	U22	U33	U12	U13	U23
N2	0.0598 (13)	0.0575 (13)	0.0569 (11)	0.0006 (10)	−0.0028 (9)	0.0056 (9)
C5	0.0501 (14)	0.0482 (14)	0.0610 (13)	0.0036 (11)	−0.0004 (10)	0.0012 (10)
N1	0.0776 (15)	0.0659 (14)	0.0613 (12)	−0.0123 (11)	−0.0069 (11)	0.0136 (10)
C3	0.0709 (18)	0.0651 (18)	0.0625 (15)	0.0030 (15)	−0.0064 (13)	0.0077 (13)
O2	0.0767 (13)	0.0716 (13)	0.0773 (11)	−0.0072 (11)	−0.0111 (9)	0.0063 (9)
C4	0.0573 (15)	0.0547 (15)	0.0653 (14)	−0.0023 (12)	0.0026 (11)	0.0063 (11)
C6	0.0498 (15)	0.0712 (18)	0.0778 (17)	−0.0037 (13)	−0.0045 (12)	0.0056 (12)
O1	0.1229 (17)	0.0917 (15)	0.0675 (11)	−0.0224 (13)	−0.0252 (11)	0.0214 (10)
C10	0.0559 (15)	0.0573 (15)	0.0643 (15)	−0.0027 (12)	−0.0024 (11)	0.0006 (11)
C8	0.0762 (19)	0.077 (2)	0.0653 (15)	0.0128 (16)	−0.0065 (14)	0.0001 (12)
C9	0.0742 (19)	0.0658 (17)	0.0666 (15)	−0.0025 (14)	0.0069 (13)	0.0058 (12)
C7	0.0577 (17)	0.089 (2)	0.0783 (17)	−0.0010 (15)	−0.0175 (14)	−0.0027 (15)
C2	0.174 (4)	0.142 (3)	0.082 (2)	−0.046 (3)	−0.063 (2)	0.026 (2)
C1	0.172 (5)	0.231 (6)	0.096 (3)	−0.051 (4)	−0.045 (3)	0.054 (3)

N2—C4	1.275 (3)	C10—C9	1.379 (3)
N2—N1	1.377 (2)	C10—H10A	0.9300
C5—C10	1.389 (3)	C8—C7	1.372 (4)
C5—C6	1.394 (3)	C8—C9	1.378 (4)
C5—C4	1.462 (3)	C8—H8A	0.9300
N1—C3	1.345 (3)	C9—H9A	0.9300
N1—H1A	0.8600	C7—H7A	0.9300
C3—O2	1.210 (3)	C2—C1	1.417 (5)
C3—O1	1.334 (3)	C2—H2B	0.9700
C4—H4A	0.9300	C2—H2C	0.9700
C6—C7	1.378 (3)	C1—H1B	0.9600
C6—H6A	0.9300	C1—H1C	0.9600
O1—C2	1.457 (4)	C1—H1D	0.9600
C4—N2—N1	114.8 (2)	C7—C8—H8A	119.9
C10—C5—C6	118.5 (2)	C9—C8—H8A	119.9
C10—C5—C4	121.8 (2)	C8—C9—C10	120.3 (3)
C6—C5—C4	119.5 (2)	C8—C9—H9A	119.9
C3—N1—N2	119.3 (2)	C10—C9—H9A	119.9
C3—N1—H1A	120.4	C8—C7—C6	119.8 (3)
N2—N1—H1A	120.4	C8—C7—H7A	120.1
O2—C3—O1	124.3 (2)	C6—C7—H7A	120.1
O2—C3—N1	126.3 (2)	C1—C2—O1	108.7 (3)
O1—C3—N1	109.3 (3)	C1—C2—H2B	109.9
N2—C4—C5	121.6 (2)	O1—C2—H2B	109.9
N2—C4—H4A	119.2	C1—C2—H2C	109.9
C5—C4—H4A	119.2	O1—C2—H2C	109.9
C7—C6—C5	120.8 (3)	H2B—C2—H2C	108.3
C7—C6—H6A	119.6	C2—C1—H1B	109.5
C5—C6—H6A	119.6	C2—C1—H1C	109.5
C3—O1—C2	116.0 (2)	H1B—C1—H1C	109.5
C9—C10—C5	120.3 (2)	C2—C1—H1D	109.5
C9—C10—H10A	119.8	H1B—C1—H1D	109.5
C5—C10—H10A	119.8	H1C—C1—H1D	109.5
C7—C8—C9	120.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.04	2.885 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.04	2.885 (3)	168

Symmetry code: (i) .