Ethyl 3-benzyl­idenecarbazate

Jiang, J.-H.

doi:10.1107/S1600536810048865

organic compounds

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Volume 66| Part 12| December 2010| Page o3337

https://doi.org/10.1107/S1600536810048865

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Ethyl 3-benzylidenecarbazate

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weifangjjh@126.com

(Received 22 November 2010; accepted 23 November 2010; online 27 November 2010)

In the title compound, C₁₀H₁₂N₂O₂, 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, molecules 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_r = 192.22
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.206
S = 1.00
2449 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048865/hb5754sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048865/hb5754Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

A mixture of benzaldehyde (0.01 mol) and ethyl carbazate (0.01 mol) was stirred in refluxing ethanol (20 mL) for 2 h to afford the title compound (0.095 mol, yield 95%). Colourless blocks were obtained by recrystallization from ethanol at room temperature.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids.

Ethyl 3-benzylidenecarbazate top

Crystal data top

C₁₀H₁₂N₂O₂	D_x = 1.193 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1041P)²] where P = (F_o² + 2F_c²)/3
2449 reflections	(Δ/σ)_max < 0.001
127 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₁₂N₂O₂	V = 2140.8 (7) Å³
M_r = 192.22	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.309 (2) Å	µ = 0.09 mm⁻¹
b = 7.6693 (15) Å	T = 293 K
c = 24.684 (5) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	1147 reflections with I > 2σ(I)
19439 measured reflections	R_int = 0.100
2449 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.206	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
2449 reflections	Δρ_min = −0.22 e Å⁻³
127 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O₂
M_r	192.22
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	11.309 (2), 7.6693 (15), 24.684 (5)
V (Å³)	2140.8 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19439, 2449, 1147
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.206, 1.00
No. of reflections	2449
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3337

https://doi.org/10.1107/S1600536810048865

Open

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