Ethyl 3-[1-(2-hydroxy­phen­yl)eth­ylidene]carbazate

Li, Y.-F.; Liu, H.-X.; Jian, F.-F.

doi:10.1107/S1600536809044602

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2935

https://doi.org/10.1107/S1600536809044602

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Ethyl 3-[1-(2-hydroxyphenyl)ethylidene]carbazate

Yu-Feng Li,^a Hai-Xing Liu ^a and Fang-Fang Jian ^b ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 22 October 2009; accepted 27 October 2009; online 31 October 2009)

The title compound, C₁₁H₁₄N₂O₃, was prepared by the reaction of ethyl carbazate and 1-(2-hydroxyphenyl)ethanone. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, forming centrosymmetric dimers. An intramolecular O—H⋯N interaction also occurs.

Related literature

For the applications of Schiff base compounds, see: Cimerman et al. (1997 ); Forthe C=N double-bond length in a related structure, see: Girgis (2006 ).

Experimental

Crystal data

C₁₁H₁₄N₂O₃
M_r = 222.24
Triclinic, $[P \overline 1]$
a = 5.4830 (11) Å
b = 10.191 (2) Å
c = 11.410 (2) Å
α = 112.53 (3)°
β = 95.79 (3)°
γ = 99.68 (3)°
V = 570.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.491, T_max = 0.728
5650 measured reflections
2597 independent reflections
1839 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.180
S = 1.08
2597 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.92 (2)	2.05 (2)	2.9649 (19)	170.4 (16)
O3—H3A⋯N1	0.98 (3)	1.68 (3)	2.5728 (19)	149 (2)
Symmetry code: (i) -x, -y, -z+2.

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/S1600536809044602/lh2935sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044602/lh2935Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature and have potential analytical applications (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and its crystal structure is determined herein.

The molecular structure of (I) is shown in Fig. 1. The C7—N1 bond length of 1.2836 (18)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006). In the crystal structure, molecules are linked by intermolecular N—H···O hydrogen bonds to form centrosymmetric dimers.

Related literature top

For the applications of Schiff base compounds, see: Cimerman et al. (1997); Forthe C═N double-bond length in a related structure, see: Girgis (2006).

Experimental top

A mixture of the 1-(2-hydroxyphenyl)ethanone (0.1 mol), and Ethyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.082 mol, yield 82%). Single crystals suitable for X-ray measurements were obtained by recrystallization of (I) from ethanol at room temperature.

Structure description top

For the applications of Schiff base compounds, see: Cimerman et al. (1997); Forthe C═N double-bond length in a related structure, see: Girgis (2006).

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 molecular structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Ethyl 3-[1-(2-hydroxyphenyl)ethylidene]carbazate top

Crystal data top

C₁₁H₁₄N₂O₃	Z = 2
M_r = 222.24	F(000) = 236
Triclinic, P1	D_x = 1.293 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4830 (11) Å	Cell parameters from 1974 reflections
b = 10.191 (2) Å	θ = 3.5–27.5°
c = 11.410 (2) Å	µ = 0.10 mm⁻¹
α = 112.53 (3)°	T = 293 K
β = 95.79 (3)°	Block, colorless
γ = 99.68 (3)°	0.22 × 0.20 × 0.18 mm
V = 570.9 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	2597 independent reflections
Radiation source: fine-focus sealed tube	1839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
φ and ω scans	θ_max = 27.5°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
T_min = 0.491, T_max = 0.728	k = −13→13
5650 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.180	w = 1/[σ²(F_o²) + (0.1217P)² + 0.0113P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.003
2597 reflections	Δρ_max = 0.23 e Å⁻³
166 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (14)

Crystal data top

C₁₁H₁₄N₂O₃	γ = 99.68 (3)°
M_r = 222.24	V = 570.9 (2) Å³
Triclinic, P1	Z = 2
a = 5.4830 (11) Å	Mo Kα radiation
b = 10.191 (2) Å	µ = 0.10 mm⁻¹
c = 11.410 (2) Å	T = 293 K
α = 112.53 (3)°	0.22 × 0.20 × 0.18 mm
β = 95.79 (3)°

Data collection top

Bruker SMART CCD diffractometer	2597 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1839 reflections with I > 2σ(I)
T_min = 0.491, T_max = 0.728	R_int = 0.016
5650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.23 e Å⁻³
2597 reflections	Δρ_min = −0.23 e Å⁻³
166 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
O3	0.4674 (2)	0.34070 (13)	0.74631 (11)	0.0681 (4)
O1	0.2984 (2)	0.09910 (13)	1.08787 (10)	0.0676 (4)
O2	0.52301 (18)	0.24189 (11)	1.00894 (9)	0.0549 (3)
N1	0.1757 (2)	0.16596 (12)	0.81259 (10)	0.0476 (3)
N2	0.1444 (2)	0.10360 (14)	0.89965 (11)	0.0536 (3)
C1	0.0453 (2)	0.20676 (14)	0.63011 (12)	0.0453 (3)
C9	0.3238 (3)	0.14591 (16)	1.00535 (13)	0.0505 (4)
C7	−0.0055 (2)	0.13722 (14)	0.71973 (12)	0.0440 (3)
C3	0.3121 (3)	0.36489 (19)	0.55821 (16)	0.0682 (5)
H3B	0.4653	0.4273	0.5690	0.082*
C2	0.2752 (3)	0.30312 (15)	0.64688 (14)	0.0512 (4)
C10	0.7203 (3)	0.29608 (19)	1.12246 (15)	0.0635 (4)
H10A	0.7912	0.2169	1.1274	0.076*
H10B	0.6526	0.3396	1.2002	0.076*
C8	−0.2561 (3)	0.0382 (2)	0.69869 (19)	0.0638 (5)
C5	−0.0996 (4)	0.2415 (2)	0.43765 (17)	0.0728 (5)
H5A	−0.2254	0.2202	0.3677	0.087*
C6	−0.1370 (3)	0.17999 (19)	0.52442 (16)	0.0626 (4)
H6A	−0.2912	0.1176	0.5120	0.075*
C4	0.1279 (4)	0.3354 (2)	0.45604 (17)	0.0737 (5)
H4A	0.1555	0.3787	0.3987	0.088*
C11	0.9167 (3)	0.40714 (19)	1.10931 (17)	0.0706 (5)
H11A	1.0503	0.4458	1.1829	0.106*
H11B	0.8441	0.4846	1.1043	0.106*
H11C	0.9825	0.3626	1.0323	0.106*
H3A	0.407 (5)	0.283 (3)	0.794 (2)	0.107 (8)*
H2A	−0.001 (4)	0.039 (2)	0.8940 (17)	0.074 (5)*
H8A	−0.392 (5)	0.072 (3)	0.670 (2)	0.127 (9)*
H8B	−0.298 (5)	0.034 (3)	0.767 (3)	0.133 (10)*
H8C	−0.259 (6)	−0.042 (4)	0.637 (3)	0.139 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0548 (6)	0.0760 (7)	0.0715 (7)	−0.0132 (5)	−0.0027 (5)	0.0428 (6)
O1	0.0639 (7)	0.0847 (8)	0.0621 (6)	−0.0099 (5)	−0.0004 (5)	0.0522 (6)
O2	0.0530 (6)	0.0615 (6)	0.0509 (5)	−0.0086 (4)	−0.0006 (4)	0.0349 (5)
N1	0.0485 (6)	0.0524 (6)	0.0464 (6)	0.0009 (4)	0.0051 (5)	0.0302 (5)
N2	0.0497 (7)	0.0614 (7)	0.0534 (6)	−0.0050 (5)	0.0018 (5)	0.0365 (5)
C1	0.0476 (7)	0.0474 (7)	0.0444 (7)	0.0075 (5)	0.0079 (5)	0.0239 (5)
C9	0.0533 (7)	0.0528 (7)	0.0499 (7)	0.0019 (6)	0.0069 (6)	0.0306 (6)
C7	0.0426 (6)	0.0461 (7)	0.0435 (6)	0.0042 (5)	0.0072 (5)	0.0209 (5)
C3	0.0708 (10)	0.0677 (10)	0.0746 (10)	−0.0033 (7)	0.0139 (8)	0.0458 (8)
C2	0.0524 (8)	0.0489 (7)	0.0534 (7)	0.0032 (5)	0.0080 (6)	0.0257 (6)
C10	0.0605 (9)	0.0695 (10)	0.0554 (8)	−0.0072 (7)	−0.0040 (7)	0.0326 (7)
C8	0.0498 (8)	0.0802 (11)	0.0650 (9)	−0.0084 (7)	0.0004 (7)	0.0454 (9)
C5	0.0723 (11)	0.0932 (13)	0.0665 (9)	0.0105 (9)	0.0020 (8)	0.0531 (9)
C6	0.0535 (8)	0.0794 (10)	0.0601 (8)	0.0011 (7)	0.0020 (7)	0.0417 (8)
C4	0.0878 (12)	0.0808 (11)	0.0724 (10)	0.0118 (9)	0.0155 (9)	0.0552 (9)
C11	0.0631 (9)	0.0640 (10)	0.0740 (10)	−0.0072 (7)	0.0042 (8)	0.0274 (8)

Geometric parameters (Å, º) top

O3—C2	1.3543 (19)	C3—H3B	0.9300
O3—H3A	0.98 (2)	C10—C11	1.489 (2)
O1—C9	1.2173 (16)	C10—H10A	0.9700
O2—C9	1.3237 (17)	C10—H10B	0.9700
O2—C10	1.4563 (18)	C8—H8A	0.95 (3)
N1—C7	1.2836 (18)	C8—H8B	0.85 (3)
N1—N2	1.3790 (15)	C8—H8C	0.84 (3)
N2—C9	1.3521 (19)	C5—C6	1.374 (2)
N2—H2A	0.92 (2)	C5—C4	1.381 (3)
C1—C6	1.393 (2)	C5—H5A	0.9300
C1—C2	1.408 (2)	C6—H6A	0.9300
C1—C7	1.4737 (18)	C4—H4A	0.9300
C7—C8	1.4988 (19)	C11—H11A	0.9600
C3—C4	1.365 (2)	C11—H11B	0.9600
C3—C2	1.395 (2)	C11—H11C	0.9600

C2—O3—H3A	104.2 (15)	O2—C10—H10B	110.3
C9—O2—C10	116.29 (10)	C11—C10—H10B	110.3
C7—N1—N2	119.65 (11)	H10A—C10—H10B	108.6
C9—N2—N1	119.71 (11)	C7—C8—H8A	112.7 (16)
C9—N2—H2A	116.8 (11)	C7—C8—H8B	114 (2)
N1—N2—H2A	123.3 (11)	H8A—C8—H8B	101 (2)
C6—C1—C2	116.97 (12)	C7—C8—H8C	107 (2)
C6—C1—C7	120.60 (12)	H8A—C8—H8C	105 (3)
C2—C1—C7	122.43 (12)	H8B—C8—H8C	117 (3)
O1—C9—O2	124.75 (13)	C6—C5—C4	118.87 (16)
O1—C9—N2	121.90 (13)	C6—C5—H5A	120.6
O2—C9—N2	113.34 (11)	C4—C5—H5A	120.6
N1—C7—C1	116.09 (11)	C5—C6—C1	123.05 (15)
N1—C7—C8	123.84 (12)	C5—C6—H6A	118.5
C1—C7—C8	120.06 (12)	C1—C6—H6A	118.5
C4—C3—C2	121.27 (14)	C3—C4—C5	120.15 (14)
C4—C3—H3B	119.4	C3—C4—H4A	119.9
C2—C3—H3B	119.4	C5—C4—H4A	119.9
O3—C2—C3	117.02 (13)	C10—C11—H11A	109.5
O3—C2—C1	123.31 (12)	C10—C11—H11B	109.5
C3—C2—C1	119.67 (13)	H11A—C11—H11B	109.5
O2—C10—C11	107.04 (13)	C10—C11—H11C	109.5
O2—C10—H10A	110.3	H11A—C11—H11C	109.5
C11—C10—H10A	110.3	H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.92 (2)	2.05 (2)	2.9649 (19)	170.4 (16)
O3—H3A···N1	0.98 (3)	1.68 (3)	2.5728 (19)	149 (2)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O₃
M_r	222.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.4830 (11), 10.191 (2), 11.410 (2)
α, β, γ (°)	112.53 (3), 95.79 (3), 99.68 (3)
V (Å³)	570.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.491, 0.728
No. of measured, independent and observed [I > 2σ(I)] reflections	5650, 2597, 1839
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.180, 1.08
No. of reflections	2597
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

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
N2—H2A···O1ⁱ	0.92 (2)	2.05 (2)	2.9649 (19)	170.4 (16)
O3—H3A···N1	0.98 (3)	1.68 (3)	2.5728 (19)	149 (2)

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

The authors would like to thank the Science Foundation of WeiFang University (No. 2009Z24).

References

Bruker (1997). SMART and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar