2-[(4-Chloro­phenyl)­amino­meth­yl]phenol

Xu, J.

doi:10.1107/S1600536811032557

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2364

doi:10.1107/S1600536811032557

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2-[(4-Chlorophenyl)aminomethyl]phenol

Jie Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chemcrystal66@yahoo.com.cn

(Received 20 July 2011; accepted 11 August 2011; online 17 August 2011)

In the title molecule, C₁₃H₁₂ClNO, the two benzene rings are twisted from each other by a dihedral angle of 68.60 (8)°. In the crystal structure, the hydroxy and amino H atoms are involved in intermolecular hydrogen bonds, O—H⋯N and N—H⋯O, respectively, resulting in R⁴₄(8) loops about inversion centers.

Related literature

For the properties and structures of related amino compounds, see: Fu et al. (2007 , 2008 , 2009 ); Fu & Xiong (2008 ). For a description of ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₂ClNO
M_r = 233.69
Triclinic, $[P \overline 1]$
a = 5.5842 (11) Å
b = 7.9485 (16) Å
c = 13.023 (3) Å
α = 86.87 (3)°
β = 89.12 (3)°
γ = 88.65 (3)°
V = 577.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.10 × 0.03 × 0.03 mm

Data collection

Mercury2 (2×2 bin mode) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.910, T_max = 1.000
5968 measured reflections
2637 independent reflections
1383 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.187
S = 0.98
2637 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	1.97	2.780 (3)	171
N1—H1A⋯O1ⁱⁱ	0.89	2.17	3.037 (3)	165
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536811032557/pv2434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032557/pv2434Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032557/pv2434Isup3.cml

checkCIF report

Comment top

Organic amino compounds have attracted much attention as phase transition dielectric materials for their application in memory storage (Fu et al., 2007; Fu & Xiong 2008; Fu et al., 2008; Fu et al., 2009). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have developed a series of new organic molecules. In this article, we describe the crystal structure of the title compound.

In the title molecule (Fig. 1), the two benzene rings are twisted from each other by a dihedral angle of 68.60 (8)°. In the crystal structure, the hydroxyl and amino H atoms are involved in intermolecular hydrogen bonds, O1—H1···N1 and N1—H1A···O1, respectively, resulting in a R⁴₄(8) ring motif (Bernstein et al., 1995) about inversion centers, which plays an important role in stabilizing the crystal structure. The R⁴₄(8) motif units are further linked into a one-dimentional chain along the b axis (Table 1 and Fig. 2).

Related literature top

For the properties and structures of related amino compounds, see: Fu et al. (2007, 2008, 2009); Fu & Xiong (2008). For a description of ring motifs, see: Bernstein et al. (1995).

Experimental top

The commercial 2-((4-chlorophenylamino)methyl)phenol (3 mmol) was dissolved in water/EtOH (1:1 v/v) solution. The solvent was slowly evaporated in air affording colourless block-shaped crystals of the title compound suitable for X-ray analysis.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. The crystal packing of the title compound, showing the one-dimensional chain. H atoms not involved in hydrogen bonding (dashed line) have been omitted for clarity.

2-[(4-Chlorophenyl)aminomethyl]phenol top

Crystal data top

C₁₃H₁₂ClNO	Z = 2
M_r = 233.69	F(000) = 244
Triclinic, P1	D_x = 1.345 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5842 (11) Å	Cell parameters from 2637 reflections
b = 7.9485 (16) Å	θ = 3.2–27.5°
c = 13.023 (3) Å	µ = 0.31 mm⁻¹
α = 86.87 (3)°	T = 298 K
β = 89.12 (3)°	Block, colorless
γ = 88.65 (3)°	0.10 × 0.03 × 0.03 mm
V = 577.0 (2) Å³

Data collection top

Mercury2 (2x2 bin mode) diffractometer	2637 independent reflections
Radiation source: fine-focus sealed tube	1383 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD profile fitting scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.910, T_max = 1.000	l = −16→16
5968 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.082P)²] where P = (F_o² + 2F_c²)/3
2637 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₃H₁₂ClNO	γ = 88.65 (3)°
M_r = 233.69	V = 577.0 (2) Å³
Triclinic, P1	Z = 2
a = 5.5842 (11) Å	Mo Kα radiation
b = 7.9485 (16) Å	µ = 0.31 mm⁻¹
c = 13.023 (3) Å	T = 298 K
α = 86.87 (3)°	0.10 × 0.03 × 0.03 mm
β = 89.12 (3)°

Data collection top

Mercury2 (2x2 bin mode) diffractometer	2637 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1383 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.061
5968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 0.98	Δρ_max = 0.22 e Å⁻³
2637 reflections	Δρ_min = −0.25 e Å⁻³
145 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.3943 (2)	0.26250 (15)	−0.02082 (7)	0.1028 (5)
O1	1.2067 (3)	0.3735 (2)	0.53925 (13)	0.0478 (5)
H1	1.2487	0.4639	0.5596	0.057*
N1	0.6595 (4)	0.3048 (2)	0.41481 (16)	0.0425 (6)
H1A	0.5273	0.3047	0.4539	0.051*
C1	1.0518 (4)	0.2978 (3)	0.60896 (19)	0.0394 (6)
C6	0.8691 (4)	0.2033 (3)	0.5715 (2)	0.0430 (7)
C8	0.5997 (4)	0.2890 (3)	0.3104 (2)	0.0420 (6)
C2	1.0819 (5)	0.3070 (3)	0.7143 (2)	0.0503 (7)
H2A	1.2081	0.3667	0.7391	0.060*
C7	0.8410 (5)	0.1848 (3)	0.4587 (2)	0.0499 (7)
H7A	0.9936	0.2038	0.4239	0.060*
H7B	0.7942	0.0706	0.4472	0.060*
C5	0.7158 (5)	0.1240 (4)	0.6422 (3)	0.0593 (8)
H5A	0.5925	0.0603	0.6186	0.071*
C13	0.3944 (5)	0.3687 (4)	0.2737 (2)	0.0519 (7)
H13A	0.2966	0.4278	0.3183	0.062*
C9	0.7429 (5)	0.2015 (4)	0.2432 (2)	0.0544 (8)
H9A	0.8824	0.1468	0.2666	0.065*
C11	0.4753 (6)	0.2735 (4)	0.1065 (2)	0.0612 (8)
C12	0.3308 (6)	0.3628 (4)	0.1723 (2)	0.0620 (8)
H12A	0.1924	0.4182	0.1484	0.074*
C3	0.9239 (5)	0.2273 (4)	0.7814 (2)	0.0588 (8)
H3A	0.9423	0.2353	0.8518	0.071*
C10	0.6794 (6)	0.1947 (4)	0.1411 (2)	0.0642 (9)
H10A	0.7768	0.1361	0.0961	0.077*
C4	0.7407 (6)	0.1367 (4)	0.7467 (2)	0.0632 (9)
H4A	0.6338	0.0841	0.7929	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1312 (10)	0.1295 (10)	0.0494 (6)	−0.0067 (7)	−0.0159 (6)	−0.0148 (6)
O1	0.0486 (11)	0.0435 (11)	0.0524 (12)	−0.0078 (9)	0.0067 (9)	−0.0115 (9)
N1	0.0386 (12)	0.0443 (13)	0.0451 (13)	0.0034 (10)	0.0031 (10)	−0.0089 (10)
C1	0.0347 (13)	0.0364 (14)	0.0470 (16)	0.0056 (11)	0.0013 (12)	−0.0042 (12)
C6	0.0387 (14)	0.0374 (14)	0.0533 (17)	0.0010 (12)	−0.0030 (12)	−0.0050 (13)
C8	0.0392 (14)	0.0426 (15)	0.0447 (16)	−0.0073 (12)	0.0031 (12)	−0.0065 (12)
C2	0.0465 (16)	0.0529 (18)	0.0519 (18)	0.0009 (13)	−0.0075 (13)	−0.0044 (14)
C7	0.0443 (15)	0.0446 (16)	0.0619 (19)	0.0037 (13)	−0.0050 (13)	−0.0134 (14)
C5	0.0491 (17)	0.0526 (18)	0.077 (2)	−0.0091 (14)	−0.0073 (16)	−0.0022 (16)
C13	0.0522 (17)	0.0561 (18)	0.0474 (17)	0.0055 (14)	0.0029 (13)	−0.0063 (14)
C9	0.0459 (16)	0.0616 (18)	0.0575 (19)	0.0015 (14)	0.0018 (14)	−0.0215 (15)
C11	0.069 (2)	0.068 (2)	0.0470 (18)	−0.0101 (18)	−0.0010 (16)	−0.0071 (16)
C12	0.0618 (19)	0.069 (2)	0.0548 (19)	0.0018 (16)	−0.0088 (15)	0.0042 (16)
C3	0.067 (2)	0.064 (2)	0.0447 (18)	0.0054 (17)	−0.0007 (15)	0.0034 (15)
C10	0.068 (2)	0.070 (2)	0.057 (2)	−0.0048 (17)	0.0071 (16)	−0.0235 (17)
C4	0.062 (2)	0.066 (2)	0.059 (2)	−0.0058 (17)	0.0084 (16)	0.0117 (17)

Geometric parameters (Å, º) top

Cl1—C11	1.733 (3)	C7—H7B	0.9700
O1—C1	1.369 (3)	C5—C4	1.380 (4)
O1—H1	0.8202	C5—H5A	0.9300
N1—C8	1.417 (3)	C13—C12	1.376 (4)
N1—C7	1.476 (3)	C13—H13A	0.9300
N1—H1A	0.8898	C9—C10	1.386 (4)
C1—C2	1.390 (3)	C9—H9A	0.9300
C1—C6	1.391 (4)	C11—C10	1.358 (4)
C6—C5	1.384 (4)	C11—C12	1.381 (4)
C6—C7	1.495 (4)	C12—H12A	0.9300
C8—C13	1.376 (4)	C3—C4	1.361 (4)
C8—C9	1.382 (4)	C3—H3A	0.9300
C2—C3	1.374 (4)	C10—H10A	0.9300
C2—H2A	0.9300	C4—H4A	0.9300
C7—H7A	0.9700

C1—O1—H1	110.1	C4—C5—H5A	119.1
C8—N1—C7	117.0 (2)	C6—C5—H5A	119.1
C8—N1—H1A	110.1	C12—C13—C8	121.4 (3)
C7—N1—H1A	110.7	C12—C13—H13A	119.3
O1—C1—C2	121.5 (2)	C8—C13—H13A	119.3
O1—C1—C6	117.9 (2)	C8—C9—C10	120.2 (3)
C2—C1—C6	120.5 (2)	C8—C9—H9A	119.9
C5—C6—C1	117.8 (3)	C10—C9—H9A	119.9
C5—C6—C7	120.8 (2)	C10—C11—C12	120.4 (3)
C1—C6—C7	121.3 (2)	C10—C11—Cl1	120.1 (3)
C13—C8—C9	118.6 (3)	C12—C11—Cl1	119.5 (3)
C13—C8—N1	118.6 (2)	C13—C12—C11	119.1 (3)
C9—C8—N1	122.7 (3)	C13—C12—H12A	120.4
C3—C2—C1	119.5 (3)	C11—C12—H12A	120.4
C3—C2—H2A	120.3	C4—C3—C2	121.2 (3)
C1—C2—H2A	120.3	C4—C3—H3A	119.4
N1—C7—C6	111.5 (2)	C2—C3—H3A	119.4
N1—C7—H7A	109.3	C11—C10—C9	120.2 (3)
C6—C7—H7A	109.3	C11—C10—H10A	119.9
N1—C7—H7B	109.3	C9—C10—H10A	119.9
C6—C7—H7B	109.3	C3—C4—C5	119.1 (3)
H7A—C7—H7B	108.0	C3—C4—H4A	120.5
C4—C5—C6	121.9 (3)	C5—C4—H4A	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.97	2.780 (3)	171
N1—H1A···O1ⁱⁱ	0.89	2.17	3.037 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂ClNO
M_r	233.69
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.5842 (11), 7.9485 (16), 13.023 (3)
α, β, γ (°)	86.87 (3), 89.12 (3), 88.65 (3)
V (Å³)	577.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.10 × 0.03 × 0.03

Data collection
Diffractometer	Mercury2 (2x2 bin mode) diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.910, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5968, 2637, 1383
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.187, 0.98
No. of reflections	2637
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: CrystalClear (Rigaku, 2005), 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
O1—H1···N1ⁱ	0.82	1.97	2.780 (3)	171
N1—H1A···O1ⁱⁱ	0.89	2.17	3.037 (3)	165

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

Acknowledgements

This work was supported by a start-up Grant of Southeast University, China.

References

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