2-{[(2-Hy­droxy-3,5-dimethyl­benz­yl)(meth­yl)amino]­meth­yl}-4,6-dimethyl­phenol

Veranitisagul, C.; Wattanathana, W.; Kaewvilai, A.; Duangthongyou, T.; Laobuthee, A.; Koonsaeng, N.

doi:10.1107/S1600536812022180

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1826

doi:10.1107/S1600536812022180

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2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol

Chatchai Veranitisagul,^a Worawat Wattanathana,^b Attaphon Kaewvilai,^c Tanwawan Duangthongyou,^b Apirat Laobuthee ^c and Nattamon Koonsaeng ^b ^*

^aDepartment of Materials and Metallurgical Engineering, Faculty of Engineering, Rajamangala University of Technology Thanyaburi, Pathumthani 12110, Thailand, ^bDepartment of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand, and ^cDepartment of Materials Engineering, Faculty of Engineering, Kasetsart University, Bangkok 10900, Thailand
^*Correspondence e-mail: fscinmk@ku.ac.th

(Received 11 May 2012; accepted 16 May 2012; online 19 May 2012)

In the title compound, C₁₉H₂₅NO₂, the dihedral angle between the benzene rings is 53.15 (8)°. One of the –OH groups forms an intramolecular O—H⋯N link, generating an S(6) ring. The other –OH group forms an intermolecular O—H⋯N hydrogen bond in the crystal, generating centrosymmetric R₂²(20) loops.

Related literature

For the synthesis, see: Chirachanchai et al. (2009 ). For metal-responsive properties of N,N-bis(2-hydroxybenzyl)alkylamines, see: Veranitisagul et al. (2011 ). For the use of N,N-bis(2-hydroxybenzyl)alkylamines in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008 ).

Experimental

Crystal data

C₁₉H₂₅NO₂
M_r = 299.40
Triclinic, $[P \overline 1]$
a = 5.4598 (4) Å
b = 12.3285 (12) Å
c = 13.0441 (13) Å
α = 95.412 (3)°
β = 96.482 (2)°
γ = 94.238 (2)°
V = 865.33 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.52 × 0.30 × 0.24 mm

Data collection

Siemens P4 diffractometer
6613 measured reflections
3944 independent reflections
2722 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.182
S = 1.06
3944 reflections
299 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H′⋯N	1.03 (3)	1.71 (3)	2.6895 (18)	156 (2)
O2—H′′⋯O1ⁱ	0.94 (3)	2.02 (4)	2.9114 (18)	158 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: XSCANS (Siemens, 1992 ); cell refinement: XSCANS; data reduction: XSCANS; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022180/hb6793sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022180/hb6793Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022180/hb6793Isup3.cml

checkCIF report

Related literature top

For the synthesis, see: Chirachanchai et al. (2009). For metal-responsive properties of N,N-bis(2-hydroxybenzyl)alkylamines, see: Veranitisagul et al. (2011). For the use of N,N-bis(2-hydroxybenzyl)alkylamines in the synthesis of macrocyclic molecules, see: Rungsimanon et al. (2008).

Experimental top

The preparation of the title compound was reported elsewhere (Chirachanchai et al., 2009). Colorless blocks were recrystallized from 2-propanol solution.

Computing details top

Data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS (Siemens, 1992); data reduction: XSCANS (Siemens, 1992); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound (arbitrary spheres for the H atoms).
	Fig. 2. The packing structure of compound (Hydrogen bonds indicated by dash lines).

2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol top

Crystal data top

C₁₉H₂₅NO₂	Z = 2
M_r = 299.40	F(000) = 324
Triclinic, P1	D_x = 1.149 Mg m⁻³
a = 5.4598 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3285 (12) Å	Cell parameters from 2370 reflections
c = 13.0441 (13) Å	θ = 3.2–27.2°
α = 95.412 (3)°	µ = 0.07 mm⁻¹
β = 96.482 (2)°	T = 296 K
γ = 94.238 (2)°	Block, colorless
V = 865.33 (14) Å³	0.52 × 0.30 × 0.24 mm

Data collection top

Siemens P4 diffractometer	2722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 27.6°, θ_min = 1.6°
ω scans	h = −6→7
6613 measured reflections	k = −16→15
3944 independent reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.1149P)²] where P = (F_o² + 2F_c²)/3
3944 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₂₅NO₂	γ = 94.238 (2)°
M_r = 299.40	V = 865.33 (14) Å³
Triclinic, P1	Z = 2
a = 5.4598 (4) Å	Mo Kα radiation
b = 12.3285 (12) Å	µ = 0.07 mm⁻¹
c = 13.0441 (13) Å	T = 296 K
α = 95.412 (3)°	0.52 × 0.30 × 0.24 mm
β = 96.482 (2)°

Data collection top

Siemens P4 diffractometer	2722 reflections with I > 2σ(I)
6613 measured reflections	R_int = 0.021
3944 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.182	All H-atom parameters refined
S = 1.06	Δρ_max = 0.27 e Å⁻³
3944 reflections	Δρ_min = −0.26 e Å⁻³
299 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
O1	0.5039 (2)	0.38818 (10)	0.16018 (10)	0.0517 (3)
N	0.2371 (2)	0.21998 (11)	0.04228 (10)	0.0404 (3)
C1	0.4085 (3)	0.34523 (12)	0.24228 (13)	0.0427 (4)
C14	0.4502 (3)	0.30149 (13)	−0.15535 (12)	0.0428 (4)
C10	0.3116 (4)	0.11247 (15)	−0.20468 (13)	0.0532 (4)
C2	0.5258 (3)	0.37697 (14)	0.34231 (14)	0.0479 (4)
C6	0.1937 (3)	0.27292 (13)	0.22555 (12)	0.0423 (4)
C9	0.2935 (3)	0.20900 (14)	−0.14369 (12)	0.0435 (4)
C3	0.4254 (3)	0.33434 (15)	0.42452 (14)	0.0529 (4)
C7	0.0629 (3)	0.24498 (16)	0.11772 (13)	0.0487 (4)
C5	0.1029 (3)	0.23192 (15)	0.31059 (14)	0.0496 (4)
C13	0.6237 (3)	0.29546 (15)	−0.22569 (14)	0.0490 (4)
C8	0.1141 (3)	0.21588 (16)	−0.06464 (13)	0.0472 (4)
C11	0.4815 (4)	0.10371 (16)	−0.27587 (14)	0.0571 (5)
C4	0.2141 (3)	0.26180 (15)	0.41101 (14)	0.0529 (4)
C12	0.6338 (4)	0.19581 (17)	−0.28429 (14)	0.0556 (5)
C19	0.3486 (4)	0.11876 (15)	0.06030 (16)	0.0532 (4)
C16	0.1053 (6)	0.2193 (3)	0.50252 (19)	0.0796 (7)
C15	0.7506 (4)	0.45821 (19)	0.3588 (2)	0.0640 (5)
C18	0.7977 (4)	0.3916 (2)	−0.2386 (2)	0.0651 (6)
C17	0.4954 (9)	−0.0025 (2)	−0.3427 (2)	0.0933 (9)
O2	0.4257 (2)	0.39465 (10)	−0.09216 (10)	0.0585 (4)
H5	−0.048 (3)	0.1827 (16)	0.2992 (14)	0.052 (5)*
H12	0.751 (4)	0.1965 (19)	−0.3286 (19)	0.079 (7)*
H7B	−0.068 (4)	0.1831 (17)	0.1203 (15)	0.061 (5)*
H10	0.205 (4)	0.0478 (19)	−0.1977 (17)	0.067 (6)*
H3	0.510 (4)	0.353 (2)	0.497 (2)	0.083 (7)*
H19C	0.222 (4)	0.0535 (19)	0.0524 (17)	0.073 (6)*
H8B	−0.017 (4)	0.1503 (18)	−0.0811 (16)	0.066 (6)*
H8A	0.020 (3)	0.2867 (16)	−0.0664 (15)	0.056 (5)*
H19B	0.430 (4)	0.1259 (18)	0.1319 (19)	0.069 (6)*
H16A	−0.068 (8)	0.216 (4)	0.490 (3)	0.167 (16)*
H19A	0.466 (4)	0.1081 (18)	0.0130 (17)	0.069 (6)*
H18B	0.855 (4)	0.4335 (17)	−0.1729 (18)	0.059 (6)*
H7A	−0.030 (4)	0.3078 (17)	0.0938 (15)	0.060 (5)*
H17A	0.644 (8)	−0.001 (4)	−0.363 (4)	0.155 (17)*
H18A	0.944 (5)	0.369 (2)	−0.257 (2)	0.091 (8)*
H15B	0.827 (5)	0.459 (2)	0.433 (3)	0.110 (9)*
H15C	0.718 (4)	0.535 (2)	0.335 (2)	0.088 (7)*
H'	0.426 (5)	0.331 (2)	0.100 (2)	0.097 (8)*
H16C	0.188 (6)	0.241 (3)	0.565 (3)	0.142 (13)*
H18C	0.729 (4)	0.443 (2)	−0.276 (2)	0.086 (7)*
H''	0.483 (5)	0.457 (3)	−0.122 (2)	0.104 (9)*
H16B	0.079 (7)	0.133 (4)	0.490 (3)	0.139 (12)*
H17C	0.424 (9)	0.000 (4)	−0.409 (5)	0.184 (18)*
H15A	0.879 (5)	0.432 (2)	0.327 (2)	0.086 (8)*
H17B	0.490 (6)	−0.064 (3)	−0.304 (3)	0.136 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0599 (7)	0.0452 (7)	0.0506 (7)	−0.0098 (5)	0.0196 (6)	0.0038 (5)
N	0.0436 (7)	0.0421 (7)	0.0366 (7)	0.0005 (5)	0.0092 (5)	0.0067 (5)
C1	0.0477 (8)	0.0374 (8)	0.0446 (9)	0.0025 (6)	0.0148 (7)	0.0026 (6)
C14	0.0455 (8)	0.0447 (9)	0.0392 (8)	0.0025 (6)	0.0059 (6)	0.0098 (7)
C10	0.0697 (11)	0.0510 (10)	0.0369 (9)	−0.0053 (9)	0.0038 (8)	0.0053 (7)
C2	0.0483 (8)	0.0428 (9)	0.0521 (10)	0.0064 (7)	0.0093 (7)	−0.0029 (7)
C6	0.0434 (8)	0.0437 (9)	0.0415 (9)	0.0027 (6)	0.0124 (6)	0.0056 (7)
C9	0.0477 (8)	0.0474 (9)	0.0355 (8)	−0.0013 (7)	0.0050 (6)	0.0089 (6)
C3	0.0585 (10)	0.0568 (11)	0.0435 (10)	0.0127 (8)	0.0054 (8)	0.0006 (8)
C7	0.0412 (8)	0.0608 (11)	0.0445 (9)	−0.0020 (8)	0.0112 (7)	0.0062 (8)
C5	0.0514 (9)	0.0518 (10)	0.0479 (10)	−0.0001 (7)	0.0159 (8)	0.0083 (8)
C13	0.0454 (8)	0.0567 (10)	0.0489 (9)	0.0067 (7)	0.0072 (7)	0.0216 (8)
C8	0.0453 (8)	0.0563 (10)	0.0392 (9)	−0.0056 (8)	0.0053 (7)	0.0081 (7)
C11	0.0812 (12)	0.0549 (11)	0.0375 (9)	0.0118 (9)	0.0101 (8)	0.0082 (8)
C4	0.0618 (10)	0.0563 (10)	0.0444 (10)	0.0097 (8)	0.0168 (8)	0.0096 (8)
C12	0.0653 (11)	0.0656 (12)	0.0429 (10)	0.0187 (9)	0.0186 (8)	0.0174 (8)
C19	0.0667 (11)	0.0461 (10)	0.0479 (10)	0.0079 (8)	0.0072 (9)	0.0075 (8)
C16	0.0953 (18)	0.100 (2)	0.0474 (12)	−0.0027 (15)	0.0207 (12)	0.0215 (12)
C15	0.0553 (11)	0.0583 (13)	0.0727 (14)	−0.0043 (9)	0.0034 (10)	−0.0104 (10)
C18	0.0531 (11)	0.0650 (13)	0.0848 (17)	0.0039 (10)	0.0231 (11)	0.0303 (13)
C17	0.160 (3)	0.0665 (16)	0.0577 (15)	0.0170 (17)	0.0367 (17)	−0.0026 (12)
O2	0.0753 (8)	0.0424 (7)	0.0598 (8)	−0.0029 (6)	0.0221 (6)	0.0052 (6)

Geometric parameters (Å, º) top

O1—C1	1.3750 (19)	C13—C12	1.393 (3)
O1—H'	1.04 (3)	C13—C18	1.498 (3)
N—C19	1.456 (2)	C8—H8B	1.03 (2)
N—C7	1.472 (2)	C8—H8A	1.05 (2)
N—C8	1.473 (2)	C11—C12	1.378 (3)
C1—C2	1.394 (2)	C11—C17	1.515 (3)
C1—C6	1.403 (2)	C4—C16	1.511 (3)
C14—O2	1.373 (2)	C12—H12	0.91 (2)
C14—C13	1.392 (2)	C19—H19C	1.01 (2)
C14—C9	1.405 (2)	C19—H19B	0.98 (2)
C10—C9	1.384 (2)	C19—H19A	0.94 (2)
C10—C11	1.387 (3)	C16—H16A	0.94 (4)
C10—H10	0.97 (2)	C16—H16C	0.89 (4)
C2—C3	1.387 (3)	C16—H16B	1.05 (4)
C2—C15	1.508 (3)	C15—H15B	1.01 (3)
C6—C5	1.387 (2)	C15—H15C	1.05 (3)
C6—C7	1.501 (2)	C15—H15A	0.92 (3)
C9—C8	1.501 (2)	C18—H18B	0.96 (2)
C3—C4	1.391 (3)	C18—H18A	0.92 (3)
C3—H3	1.00 (3)	C18—H18C	0.91 (3)
C7—H7B	1.01 (2)	C17—H17A	0.88 (4)
C7—H7A	1.01 (2)	C17—H17C	0.91 (6)
C5—C4	1.384 (3)	C17—H17B	0.96 (4)
C5—H5	0.973 (18)	O2—H''	0.95 (3)

C1—O1—H'	100.4 (15)	H8B—C8—H8A	107.3 (15)
C19—N—C7	111.00 (14)	C12—C11—C10	117.31 (17)
C19—N—C8	111.41 (14)	C12—C11—C17	121.5 (2)
C7—N—C8	110.75 (12)	C10—C11—C17	121.2 (2)
O1—C1—C2	118.74 (14)	C5—C4—C3	117.52 (16)
O1—C1—C6	120.42 (15)	C5—C4—C16	121.06 (19)
C2—C1—C6	120.82 (14)	C3—C4—C16	121.40 (19)
O2—C14—C13	123.18 (14)	C11—C12—C13	123.26 (16)
O2—C14—C9	116.30 (14)	C11—C12—H12	122.7 (15)
C13—C14—C9	120.50 (16)	C13—C12—H12	114.1 (15)
C9—C10—C11	122.18 (17)	N—C19—H19C	112.4 (12)
C9—C10—H10	120.0 (13)	N—C19—H19B	108.3 (13)
C11—C10—H10	117.8 (13)	H19C—C19—H19B	107.1 (18)
C3—C2—C1	118.13 (15)	N—C19—H19A	108.2 (13)
C3—C2—C15	121.91 (17)	H19C—C19—H19A	110.3 (18)
C1—C2—C15	119.93 (17)	H19B—C19—H19A	110.5 (18)
C5—C6—C1	118.57 (15)	C4—C16—H16A	109 (3)
C5—C6—C7	121.62 (14)	C4—C16—H16C	116 (2)
C1—C6—C7	119.77 (14)	H16A—C16—H16C	123 (3)
C10—C9—C14	118.83 (15)	C4—C16—H16B	109 (2)
C10—C9—C8	121.39 (15)	H16A—C16—H16B	84 (3)
C14—C9—C8	119.77 (15)	H16C—C16—H16B	111 (3)
C2—C3—C4	122.74 (17)	C2—C15—H15B	107.5 (17)
C2—C3—H3	119.9 (13)	C2—C15—H15C	114.4 (13)
C4—C3—H3	117.3 (13)	H15B—C15—H15C	116 (2)
N—C7—C6	111.73 (13)	C2—C15—H15A	111.8 (16)
N—C7—H7B	113.6 (11)	H15B—C15—H15A	98 (2)
C6—C7—H7B	107.5 (12)	H15C—C15—H15A	109 (2)
N—C7—H7A	107.2 (11)	C13—C18—H18B	111.5 (12)
C6—C7—H7A	111.3 (11)	C13—C18—H18A	110.3 (17)
H7B—C7—H7A	105.5 (16)	H18B—C18—H18A	101 (2)
C4—C5—C6	122.20 (16)	C13—C18—H18C	114.8 (15)
C4—C5—H5	119.1 (11)	H18B—C18—H18C	102 (2)
C6—C5—H5	118.7 (11)	H18A—C18—H18C	116 (2)
C14—C13—C12	117.91 (15)	C11—C17—H17A	107 (3)
C14—C13—C18	122.03 (18)	C11—C17—H17C	111 (3)
C12—C13—C18	120.06 (17)	H17A—C17—H17C	91 (3)
N—C8—C9	112.46 (12)	C11—C17—H17B	112 (2)
N—C8—H8B	110.9 (11)	H17A—C17—H17B	104 (4)
C9—C8—H8B	108.7 (11)	H17C—C17—H17B	127 (4)
N—C8—H8A	105.3 (11)	C14—O2—H''	110.3 (18)
C9—C8—H8A	112.1 (10)

O1—C1—C2—C3	179.02 (15)	C1—C6—C5—C4	1.4 (3)
C6—C1—C2—C3	0.6 (2)	C7—C6—C5—C4	−176.34 (16)
O1—C1—C2—C15	0.9 (2)	O2—C14—C13—C12	178.87 (15)
C6—C1—C2—C15	−177.59 (17)	C9—C14—C13—C12	0.8 (2)
O1—C1—C6—C5	−179.66 (14)	O2—C14—C13—C18	−0.5 (3)
C2—C1—C6—C5	−1.2 (2)	C9—C14—C13—C18	−178.61 (17)
O1—C1—C6—C7	−1.9 (2)	C19—N—C8—C9	−65.34 (18)
C2—C1—C6—C7	176.55 (15)	C7—N—C8—C9	170.58 (14)
C11—C10—C9—C14	0.9 (3)	C10—C9—C8—N	105.66 (17)
C11—C10—C9—C8	−177.98 (17)	C14—C9—C8—N	−73.2 (2)
O2—C14—C9—C10	−179.40 (15)	C9—C10—C11—C12	−0.2 (3)
C13—C14—C9—C10	−1.2 (2)	C9—C10—C11—C17	−179.2 (2)
O2—C14—C9—C8	−0.5 (2)	C6—C5—C4—C3	−0.9 (3)
C13—C14—C9—C8	177.70 (14)	C6—C5—C4—C16	177.5 (2)
C1—C2—C3—C4	0.0 (3)	C2—C3—C4—C5	0.2 (3)
C15—C2—C3—C4	178.09 (18)	C2—C3—C4—C16	−178.2 (2)
C19—N—C7—C6	67.71 (18)	C10—C11—C12—C13	−0.3 (3)
C8—N—C7—C6	−167.98 (14)	C17—C11—C12—C13	178.8 (2)
C5—C6—C7—N	−136.72 (16)	C14—C13—C12—C11	0.0 (3)
C1—C6—C7—N	45.6 (2)	C18—C13—C12—C11	179.35 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H′···N	1.03 (3)	1.71 (3)	2.6895 (18)	156 (2)
O2—H′′···O1ⁱ	0.94 (3)	2.02 (4)	2.9114 (18)	158 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅NO₂
M_r	299.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.4598 (4), 12.3285 (12), 13.0441 (13)
α, β, γ (°)	95.412 (3), 96.482 (2), 94.238 (2)
V (Å³)	865.33 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.52 × 0.30 × 0.24

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6613, 3944, 2722
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.182, 1.06
No. of reflections	3944
No. of parameters	299
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.26

Computer programs: XSCANS (Siemens, 1992), 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—H'···N	1.03 (3)	1.71 (3)	2.6895 (18)	156 (2)
O2—H''···O1ⁱ	0.94 (3)	2.02 (4)	2.9114 (18)	158 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

This work was supported by the Thailand Research Fund (grant No. MRG5480046). The authors would like to thank the Department of Chemistry, Faculty of Science, Kasetsart University for partial support.

References

Chirachanchai, S., Laobuthee, A. & Phongtamrag, S. (2009). J. Heterocycl. Chem. 46, 714–721. Web of Science CrossRef CAS Google Scholar
Rungsimanon, T., Laobuthee, A., Miyata, M. & Chirachanchai, S. (2008). J. Incl. Phenom. Macrocycl. Chem. 62, 333–338. 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
Siemens (1992). XSCANS User's Manual. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Veranitisagul, C., Kaewvilai, A., Sangngern, S., Wattanathana, W., Suramitr, S., Koonsaeng, N. & Laobuthee, A. (2011). Int. J. Mol. Sci. 12, 4365–4377. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 68| Part 6| June 2012| Page o1826

doi:10.1107/S1600536812022180

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{[(2-Hy­dr­oxy-3,5-di­methyl­benz­yl)(meth­yl)amino]­meth­yl}-4,6-di­methyl­phenol

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{[(2-Hydroxy-3,5-dimethylbenzyl)(methyl)amino]methyl}-4,6-dimethylphenol