(3-Amino­phen­yl)methanol

Betz, R.; Gerber, T.; Hosten, E.

doi:10.1107/S1600536811029163

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2118

doi:10.1107/S1600536811029163

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(3-Aminophenyl)methanol

Richard Betz,^a ^* Thomas Gerber ^a and Eric Hosten ^a

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 12 July 2011; accepted 19 July 2011; online 23 July 2011)

In the title compound, C₇H₉NO, a derivative of benzyl alcohol, the endocyclic C—C—C angles are in the range 119.50 (12)–121.04 (12)°. In the crystal, molecules are linked by N—H⋯O hydrogen-bond interactions, forming an extended two-dimensional framework parallel to ab. O—H⋯N interactions are also observed.

Related literature

For the crystal structure of (3-(hydroxymethyl)phenyl)-bis(diphenylphosphinomethyl)amine, see: Hursthouse et al. (2003 ). For the crystal structure of 3-nitrobenzyl alcohol as a co-crystal with platinum-containing coordination compounds, see: Oskui et al. (1999 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For the use of chelating ligands in coordination chemistry, see: Gade (1998 ).

Experimental

Crystal data

C₇H₉NO
M_r = 123.15
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.7977 (4) Å
b = 6.2954 (6) Å
c = 21.6341 (18) Å
V = 653.42 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.53 × 0.47 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.869, T_max = 1.000
6010 measured reflections
961 independent reflections
924 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.11
961 reflections
94 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H81⋯N1ⁱ	0.85 (3)	2.02 (3)	2.8620 (18)	171 (2)
N1—H71⋯O1ⁱⁱ	0.87 (2)	2.19 (2)	3.0588 (16)	177 (2)
N1—H72⋯O1ⁱⁱⁱ	0.904 (19)	2.24 (2)	3.1204 (16)	165.3 (16)
Symmetry codes: (i) x, y-1, z; (ii) x+1, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029163/bx2363sup1.cif

Supporting information file. DOI: 10.1107/S1600536811029163/bx2363Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029163/bx2363Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536811029163/bx2363Isup4.cml

checkCIF report

Comment top

Chelate ligands have found widespread use in coordination chemistry due to the enhanced thermodynamic stability of resultant coordination compounds in relation to coordination compounds exclusively applying comparable monodentate ligands (Gade, 1998). Combining two different donor atoms, a molecular set-up to accomodate a large variety of metal centers of variable Lewis acidity is at hand. In this aspect, 3-aminobenzyl alcohol seemed of interest due to its possible use as a strictly neutral or, depending on the pH value, as an anionic or cationic ligand. In addition, due to the set-up of its functional groups, it may act as mono- or bidentate ligand offering the possibility to create seven-membered chelate rings. To enable comparative studies in terms of bond lengths and angles in envisioned coordination compounds, we determined the molecular and crystal structure of the title compound. Information about the crystal structure of (3-(Hydroxymethyl)phenyl)-bis(diphenylphosphinomethyl)amine (Hursthouse et al., 2003) as well as 3-nitrobenzyl alcohol as a co-crystallizate with platinum-containing coordination compounds (Oskui et al., 1999) is available in the literature.

The hydroxymethyl group is not in plane with the aromatic system, the respective dihedral angle was found at 33.0 (2) °. Endocyclic C–C–C angles hardly deviate from the expected ideal values of 120 ° and range from 119.50 (12)–121.04 (12) °. The biggest angle is found on the C atom bearing the amino group (Fig. 1).

In the crystal structure, a cooperative set of hydrogen bonds involving all nitrogen- and oxygen-bonded hydrogen atoms is present. While the oxygen atom acts as twofold acceptor for hydrogen bonds exclusively stemming from the H atoms of the amino group, the nitrogen atom of the amino group serves as acceptor for a hydrogen bond originating from the hydroxyl group's O atom. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for this hydrogen bonding system on the unitary level is C¹₁(7)C¹₁(7)C¹₁(7). In the crystal the molecules are linked by N— H···O hydrogen-bond interactions, forming an extended two-dimensional framework parallel to the ab, Fig. 2. π-Stacking is not a prominent feature of the crystal structure with the shortest intercentroid distance between two aromatic systems measured at 5.5741 (10) Å .(Fig. 2).

Related literature top

For the crystal structure of (3-(hydroxymethyl)phenyl)-bis(diphenylphosphinomethyl)amine, see: Hursthouse et al. (2003). For the crystal structure of 3-nitrobenzyl alcohol as a co-crystallizate with platinum-containing coordination compounds, see: Oskui et al. (1999). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For the use of chelate ligands in coordination chemistry, see: Gade (1998).

Experimental top

The compound was obtained commercially (Aldrich). Crystals suitable for the X-ray diffraction study were obtained upon free evaporation of a solution of the compound in acetonitrile at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. Symmetry operators: ⁱ x, y - 1, z; ⁱⁱ x - 1, y - 1, z; ⁱⁱⁱ -x + 1, y - 1/2, -z + 1/2; ^iv -x + 1, y + 1/2, -z + 1/2; ^v x, y + 1, z; ^vi x + 1, y + 1, z.

(3-Aminophenyl)methanol top

Crystal data top

C₇H₉NO	F(000) = 264
M_r = 123.15	D_x = 1.252 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5183 reflections
a = 4.7977 (4) Å	θ = 3.4–28.1°
b = 6.2954 (6) Å	µ = 0.09 mm⁻¹
c = 21.6341 (18) Å	T = 200 K
V = 653.42 (10) Å³	Platelet, brown
Z = 4	0.53 × 0.47 × 0.19 mm

Data collection top

Bruker APEXII CCD diffractometer	961 independent reflections
Radiation source: fine-focus sealed tube	924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 28.0°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
T_min = 0.869, T_max = 1.000	k = −7→8
6010 measured reflections	l = −23→28

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0484P)² + 0.1019P] where P = (F_o² + 2F_c²)/3
961 reflections	(Δ/σ)_max < 0.001
94 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₇H₉NO	V = 653.42 (10) Å³
M_r = 123.15	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.7977 (4) Å	µ = 0.09 mm⁻¹
b = 6.2954 (6) Å	T = 200 K
c = 21.6341 (18) Å	0.53 × 0.47 × 0.19 mm

Data collection top

Bruker APEXII CCD diffractometer	961 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	924 reflections with I > 2σ(I)
T_min = 0.869, T_max = 1.000	R_int = 0.020
6010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.19 e Å⁻³
961 reflections	Δρ_min = −0.16 e Å⁻³
94 parameters

Special details top

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (600 pairs) have been merged and the item was removed from the CIF.

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

	x	y	z	U_iso*/U_eq
O1	0.3733 (2)	−0.37165 (17)	0.18291 (4)	0.0277 (3)
H81	0.524 (6)	−0.439 (4)	0.1893 (9)	0.049 (6)*
N1	0.8480 (3)	0.35877 (19)	0.19920 (6)	0.0287 (3)
H71	1.002 (5)	0.432 (3)	0.1955 (9)	0.040 (5)*
H72	0.811 (4)	0.303 (3)	0.2368 (9)	0.035 (5)*
C1	0.3760 (3)	−0.2875 (2)	0.12190 (6)	0.0313 (3)
H1A	0.1858	−0.2383	0.1114	0.038*
H1B	0.4250	−0.4028	0.0927	0.038*
C2	0.5769 (3)	−0.1056 (2)	0.11274 (6)	0.0236 (3)
C3	0.6316 (3)	0.0359 (2)	0.16033 (6)	0.0252 (3)
H3	0.5471	0.0147	0.1996	0.030*
C4	0.8087 (3)	0.2089 (2)	0.15151 (6)	0.0237 (3)
C5	0.9317 (3)	0.2381 (2)	0.09359 (7)	0.0303 (3)
H5	1.0527	0.3552	0.0867	0.036*
C6	0.8774 (3)	0.0967 (2)	0.04623 (7)	0.0325 (3)
H6	0.9615	0.1177	0.0070	0.039*
C7	0.7016 (3)	−0.0758 (2)	0.05529 (6)	0.0278 (3)
H7	0.6667	−0.1727	0.0225	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0305 (5)	0.0253 (5)	0.0271 (5)	−0.0050 (5)	0.0030 (4)	0.0028 (4)
N1	0.0328 (6)	0.0248 (6)	0.0284 (6)	−0.0090 (5)	0.0021 (5)	−0.0024 (5)
C1	0.0372 (7)	0.0310 (7)	0.0259 (6)	−0.0156 (7)	−0.0035 (6)	0.0025 (5)
C2	0.0230 (6)	0.0219 (6)	0.0259 (6)	−0.0044 (5)	−0.0029 (5)	0.0024 (5)
C3	0.0274 (6)	0.0257 (6)	0.0225 (5)	−0.0066 (6)	0.0022 (5)	0.0013 (5)
C4	0.0239 (6)	0.0209 (6)	0.0265 (6)	−0.0022 (6)	−0.0011 (5)	0.0004 (5)
C5	0.0320 (7)	0.0275 (7)	0.0313 (7)	−0.0102 (6)	0.0051 (6)	0.0015 (6)
C6	0.0359 (7)	0.0359 (7)	0.0257 (6)	−0.0078 (7)	0.0071 (6)	0.0011 (6)
C7	0.0306 (6)	0.0281 (7)	0.0248 (6)	−0.0043 (6)	−0.0002 (6)	−0.0024 (5)

Geometric parameters (Å, º) top

O1—C1	1.4222 (16)	C2—C7	1.3922 (19)
O1—H81	0.85 (3)	C3—C4	1.3945 (19)
N1—C4	1.4105 (17)	C3—H3	0.9500
N1—H71	0.87 (2)	C4—C5	1.3972 (19)
N1—H72	0.904 (19)	C5—C6	1.382 (2)
C1—C2	1.5100 (19)	C5—H5	0.9500
C1—H1A	0.9900	C6—C7	1.389 (2)
C1—H1B	0.9900	C6—H6	0.9500
C2—C3	1.3865 (19)	C7—H7	0.9500

C1—O1—H81	109.2 (14)	C2—C3—H3	119.5
C4—N1—H71	113.4 (13)	C4—C3—H3	119.5
C4—N1—H72	111.9 (12)	C3—C4—C5	118.85 (12)
H71—N1—H72	117.0 (16)	C3—C4—N1	120.24 (12)
O1—C1—C2	114.20 (11)	C5—C4—N1	120.78 (12)
O1—C1—H1A	108.7	C6—C5—C4	120.04 (13)
C2—C1—H1A	108.7	C6—C5—H5	120.0
O1—C1—H1B	108.7	C4—C5—H5	120.0
C2—C1—H1B	108.7	C5—C6—C7	120.90 (13)
H1A—C1—H1B	107.6	C5—C6—H6	119.6
C3—C2—C7	119.66 (12)	C7—C6—H6	119.6
C3—C2—C1	120.72 (12)	C6—C7—C2	119.50 (12)
C7—C2—C1	119.58 (12)	C6—C7—H7	120.3
C2—C3—C4	121.04 (12)	C2—C7—H7	120.3

O1—C1—C2—C3	−33.0 (2)	C3—C4—C5—C6	−0.1 (2)
O1—C1—C2—C7	149.06 (13)	N1—C4—C5—C6	−176.05 (14)
C7—C2—C3—C4	0.4 (2)	C4—C5—C6—C7	−0.1 (2)
C1—C2—C3—C4	−177.54 (13)	C5—C6—C7—C2	0.5 (2)
C2—C3—C4—C5	0.0 (2)	C3—C2—C7—C6	−0.6 (2)
C2—C3—C4—N1	175.95 (13)	C1—C2—C7—C6	177.36 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H81···N1ⁱ	0.85 (3)	2.02 (3)	2.8620 (18)	171 (2)
N1—H71···O1ⁱⁱ	0.87 (2)	2.19 (2)	3.0588 (16)	177 (2)
N1—H72···O1ⁱⁱⁱ	0.904 (19)	2.24 (2)	3.1204 (16)	165.3 (16)

Symmetry codes: (i) x, y−1, z; (ii) x+1, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₇H₉NO
M_r	123.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	200
a, b, c (Å)	4.7977 (4), 6.2954 (6), 21.6341 (18)
V (Å³)	653.42 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.53 × 0.47 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.869, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6010, 961, 924
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.11
No. of reflections	961
No. of parameters	94
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H81···N1ⁱ	0.85 (3)	2.02 (3)	2.8620 (18)	171 (2)
N1—H71···O1ⁱⁱ	0.87 (2)	2.19 (2)	3.0588 (16)	177 (2)
N1—H72···O1ⁱⁱⁱ	0.904 (19)	2.24 (2)	3.1204 (16)	165.3 (16)

Symmetry codes: (i) x, y−1, z; (ii) x+1, y+1, z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors thank Ms Georgina Bräuer for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gade, L. H. (1998). Koordinationschemie, 1. Auflage. Weinheim: Wiley–VCH. Google Scholar
Hursthouse, M. B., Smith, M. B. & Coles, S. J. (2003). Private Communication (CCDC 662967, refcode CIRCIQ). CCDC, Cambridge, England. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oskui, B., Mintert, M. & Sheldrick, W. S. (1999). Inorg. Chim. Acta, 287, 72–81. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar