2-[(Indan-1-yl­idene)amino]­ethanol

Al-Youbi, A.O.; Asiri, A.M.; Faidallah, H.M.; Alamry, K.A.; Ng, S.W.

doi:10.1107/S1600536811032843

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2425

doi:10.1107/S1600536811032843

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2-[(Indan-1-ylidene)amino]ethanol

Abdulrahman O. Al-Youbi,^a Abdullah M. Asiri,^a,^b Hassan M. Faidallah,^a Khalid A. Alamry ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 August 2011; accepted 13 August 2011; online 27 August 2011)

The five-membed ring of the title compound, C₁₁H₁₃NO, that is fused with the aromatic ring is approximately planar (r.m.s. deviation = 0.037 Å) despite the presence of the sp³-hybridized ethylene linkage. The hydroxy group of the N-bound hydroxyethyl chain serves as hydrogen-bond donor to the azomethine N atom of an adjacent molecule, generating a hydrogen-bonded C₂-symmetric dimer.

Related literature

The related C₁₃H₁₃NO amine is a reagent in the synthesis of pharmaceuticals, see: Stange et al. (1957 ).

Experimental

Crystal data

C₁₁H₁₃NO
M_r = 175.22
Monoclinic, C 2/c
a = 16.0207 (4) Å
b = 9.2002 (2) Å
c = 13.0600 (3) Å
β = 112.855 (3)°
V = 1773.83 (7) Å³
Z = 8
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.825, T_max = 0.937
3090 measured reflections
1745 independent reflections
1590 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.02
1745 reflections
122 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.91 (2)	1.91 (2)	2.820 (1)	173 (2)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032843/bt5608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032843/bt5608Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032843/bt5608Isup3.cml

checkCIF report

Comment top

A enormously large number of Schiff base derivatives of aldehydes and ketones have been synthesized; however, 1-indanone represents an anomaly as only few have been reported. In the 2-aminoethanol derivative (Scheme I), the five-membed cyclohexene ring is planar despite the presence of sp³-hybridized ethylene linkage molecule (Fig. 1). The hydroxy group of the N-bound hydroxyethyl chain serves as hydrogen-bond donor to the azomethine N atom of an adjacent molecule to generate a hydrogen-bonded dinuclear molecule (Table 1). However, there is no significant π interaction of the rings as the distances between them exceed 3.5 Å (Fig. 2). The compound has not been reported in the chemical literature; on the other hand, the corresponding reduced amine is a reagent for the synthesis of pharmaceuticals (Stange et al., 1957).

Related literature top

The reduced C₁₃H₁₃NO amine is a reagent in the synthesis of pharmaceuticals, see: Stange et al. (1957).

Experimental top

A mixture of 2-amino ethanol (0.6 g, 10 mmol) and 1-indanone (1.3 g, 10 mmol) in dry benzene (50 ml) was refluxed in a Dean-Stark apparatus until no more water was collected (in about 2 h). The solvent was then removed under reduced pressure and the residue treated with methanol. The solid which separated out was recystalized from ethanol to give colorless, 418–419 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₃H₁₁NO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen-bonded dimer. The atoms of the aromatic rings are shown with their van der Waals surfaces.

2-[(Indan-1-ylidene)amino]ethanol top

Crystal data top

C₁₁H₁₃NO	F(000) = 752
M_r = 175.22	D_x = 1.312 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 1977 reflections
a = 16.0207 (4) Å	θ = 3.7–74.2°
b = 9.2002 (2) Å	µ = 0.67 mm⁻¹
c = 13.0600 (3) Å	T = 100 K
β = 112.855 (3)°	Prism, colorless
V = 1773.83 (7) Å³	0.30 × 0.30 × 0.10 mm
Z = 8

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1745 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1590 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.015
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 5.7°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→6
T_min = 0.825, T_max = 0.937	l = −15→16
3090 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0573P)² + 1.1159P] where P = (F_o² + 2F_c²)/3
1745 reflections	(Δ/σ)_max = 0.001
122 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₁H₁₃NO	V = 1773.83 (7) Å³
M_r = 175.22	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 16.0207 (4) Å	µ = 0.67 mm⁻¹
b = 9.2002 (2) Å	T = 100 K
c = 13.0600 (3) Å	0.30 × 0.30 × 0.10 mm
β = 112.855 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1745 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1590 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.937	R_int = 0.015
3090 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.29 e Å⁻³
1745 reflections	Δρ_min = −0.21 e Å⁻³
122 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.61199 (6)	0.25279 (9)	0.23182 (7)	0.0186 (2)
H1	0.5586 (14)	0.303 (2)	0.2000 (16)	0.051 (6)*
N1	0.54795 (6)	0.41152 (11)	0.38232 (7)	0.0155 (2)
C1	0.50616 (8)	0.78897 (13)	0.39934 (9)	0.0162 (3)
C2	0.44473 (8)	0.90379 (13)	0.36833 (10)	0.0186 (3)
H2	0.4646	1.0007	0.3891	0.022*
C3	0.35384 (8)	0.87441 (13)	0.30649 (10)	0.0194 (3)
H3	0.3114	0.9521	0.2851	0.023*
C4	0.32389 (8)	0.73221 (13)	0.27531 (9)	0.0180 (3)
H4	0.2615	0.7139	0.2334	0.022*
C5	0.38514 (8)	0.61760 (13)	0.30546 (9)	0.0160 (3)
H5	0.3653	0.5209	0.2840	0.019*
C6	0.47636 (7)	0.64727 (12)	0.36786 (9)	0.0148 (3)
C7	0.55414 (7)	0.54679 (13)	0.40624 (9)	0.0147 (3)
C8	0.63802 (7)	0.63476 (13)	0.47441 (9)	0.0174 (3)
H8A	0.6859	0.6219	0.4450	0.021*
H8B	0.6620	0.6034	0.5531	0.021*
C9	0.60731 (8)	0.79464 (13)	0.46423 (10)	0.0192 (3)
H9A	0.6218	0.8381	0.5385	0.023*
H9B	0.6372	0.8525	0.4242	0.023*
C10	0.63052 (8)	0.32330 (13)	0.42013 (9)	0.0181 (3)
H10A	0.6415	0.2820	0.4942	0.022*
H10B	0.6830	0.3850	0.4268	0.022*
C11	0.62087 (8)	0.20122 (12)	0.33805 (9)	0.0173 (3)
H11A	0.6747	0.1373	0.3680	0.021*
H11B	0.5670	0.1423	0.3299	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0162 (4)	0.0219 (4)	0.0178 (4)	0.0038 (3)	0.0067 (3)	0.0012 (3)
N1	0.0144 (5)	0.0173 (5)	0.0142 (5)	0.0019 (4)	0.0047 (4)	0.0002 (4)
C1	0.0172 (6)	0.0184 (6)	0.0147 (5)	−0.0006 (4)	0.0080 (4)	−0.0002 (4)
C2	0.0223 (6)	0.0158 (5)	0.0194 (6)	0.0006 (5)	0.0102 (5)	0.0001 (4)
C3	0.0198 (6)	0.0199 (6)	0.0197 (6)	0.0062 (5)	0.0090 (5)	0.0043 (5)
C4	0.0144 (5)	0.0230 (6)	0.0163 (5)	0.0023 (5)	0.0055 (4)	0.0018 (4)
C5	0.0158 (6)	0.0182 (6)	0.0147 (5)	−0.0002 (4)	0.0066 (4)	−0.0003 (4)
C6	0.0153 (6)	0.0168 (6)	0.0131 (5)	0.0013 (4)	0.0064 (4)	0.0005 (4)
C7	0.0128 (5)	0.0191 (6)	0.0120 (5)	−0.0007 (4)	0.0044 (4)	0.0000 (4)
C8	0.0139 (5)	0.0187 (6)	0.0171 (5)	−0.0007 (4)	0.0033 (4)	−0.0014 (4)
C9	0.0165 (6)	0.0174 (6)	0.0222 (6)	−0.0017 (4)	0.0058 (5)	−0.0031 (5)
C10	0.0144 (5)	0.0197 (6)	0.0166 (6)	0.0041 (4)	0.0020 (4)	0.0005 (4)
C11	0.0159 (5)	0.0161 (5)	0.0191 (6)	0.0028 (4)	0.0058 (4)	0.0018 (4)

Geometric parameters (Å, º) top

O1—C11	1.4201 (14)	C5—H5	0.9500
O1—H1	0.91 (2)	C6—C7	1.4742 (15)
N1—C7	1.2776 (15)	C7—C8	1.5245 (15)
N1—C10	1.4646 (14)	C8—C9	1.5403 (16)
C1—C2	1.3924 (16)	C8—H8A	0.9900
C1—C6	1.3943 (16)	C8—H8B	0.9900
C1—C9	1.5101 (16)	C9—H9A	0.9900
C2—C3	1.3900 (16)	C9—H9B	0.9900
C2—H2	0.9500	C10—C11	1.5185 (16)
C3—C4	1.3985 (17)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C4—C5	1.3890 (16)	C11—H11A	0.9900
C4—H4	0.9500	C11—H11B	0.9900
C5—C6	1.3962 (15)

C11—O1—H1	109.4 (12)	C7—C8—H8A	110.5
C7—N1—C10	118.90 (10)	C9—C8—H8A	110.5
C2—C1—C6	120.08 (11)	C7—C8—H8B	110.5
C2—C1—C9	128.34 (11)	C9—C8—H8B	110.5
C6—C1—C9	111.57 (10)	H8A—C8—H8B	108.7
C3—C2—C1	118.95 (11)	C1—C9—C8	104.63 (9)
C3—C2—H2	120.5	C1—C9—H9A	110.8
C1—C2—H2	120.5	C8—C9—H9A	110.8
C2—C3—C4	120.97 (11)	C1—C9—H9B	110.8
C2—C3—H3	119.5	C8—C9—H9B	110.8
C4—C3—H3	119.5	H9A—C9—H9B	108.9
C5—C4—C3	120.20 (11)	N1—C10—C11	109.93 (9)
C5—C4—H4	119.9	N1—C10—H10A	109.7
C3—C4—H4	119.9	C11—C10—H10A	109.7
C4—C5—C6	118.76 (11)	N1—C10—H10B	109.7
C4—C5—H5	120.6	C11—C10—H10B	109.7
C6—C5—H5	120.6	H10A—C10—H10B	108.2
C1—C6—C5	121.05 (11)	O1—C11—C10	112.74 (9)
C1—C6—C7	109.80 (10)	O1—C11—H11A	109.0
C5—C6—C7	129.11 (11)	C10—C11—H11A	109.0
N1—C7—C6	123.55 (10)	O1—C11—H11B	109.0
N1—C7—C8	128.83 (10)	C10—C11—H11B	109.0
C6—C7—C8	107.61 (10)	H11A—C11—H11B	107.8
C7—C8—C9	106.09 (9)

C6—C1—C2—C3	0.39 (17)	C10—N1—C7—C8	−2.07 (17)
C9—C1—C2—C3	178.90 (11)	C1—C6—C7—N1	−174.79 (10)
C1—C2—C3—C4	−0.12 (17)	C5—C6—C7—N1	2.73 (18)
C2—C3—C4—C5	−0.35 (18)	C1—C6—C7—C8	4.31 (12)
C3—C4—C5—C6	0.53 (16)	C5—C6—C7—C8	−178.17 (11)
C2—C1—C6—C5	−0.20 (17)	N1—C7—C8—C9	173.44 (11)
C9—C1—C6—C5	−178.95 (10)	C6—C7—C8—C9	−5.60 (12)
C2—C1—C6—C7	177.55 (10)	C2—C1—C9—C8	179.04 (11)
C9—C1—C6—C7	−1.19 (13)	C6—C1—C9—C8	−2.35 (13)
C4—C5—C6—C1	−0.26 (16)	C7—C8—C9—C1	4.78 (12)
C4—C5—C6—C7	−177.54 (10)	C7—N1—C10—C11	−148.98 (10)
C10—N1—C7—C6	176.83 (10)	N1—C10—C11—O1	63.93 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.91 (2)	1.91 (2)	2.820 (1)	173 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO
M_r	175.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	16.0207 (4), 9.2002 (2), 13.0600 (3)
β (°)	112.855 (3)
V (Å³)	1773.83 (7)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.825, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	3090, 1745, 1590
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.02
No. of reflections	1745
No. of parameters	122
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.91 (2)	1.91 (2)	2.820 (1)	173 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

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Stange, K., Friederich, H. & Amann, A. (1957). Ger. Patent 955497, 19570103. Google Scholar
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