A second ortho­rhom­bic polymorph of 2-(pyridin-4-ylmeth­oxy)phenol

Wang, G.-T.; Zhang, Y.; Yang, J.-X.; Zou, P.; Hou, G.-F.

doi:10.1107/S1600536812014067

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1366

doi:10.1107/S1600536812014067

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ADDENDA AND ERRATA

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A second orthorhombic polymorph of 2-(pyridin-4-ylmethoxy)phenol

Guang-Tu Wang,^a Yong Zhang,^a Jin-Xin Yang,^a Ping Zou ^a ^* and Guang-Feng Hou ^b

^aCollege of Life Science, Sichuan Agriculture University, Ya'an 625014, People's Republic of China, and ^bEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China
^*Correspondence e-mail: hgf1000@163.com

(Received 23 March 2012; accepted 31 March 2012; online 13 April 2012)

The crystal structure of the title compound, C₁₂H₁₁NO₂, represents a new orthorhombic polymorph II of the previously reported orthorhombic form I [Zhang et al. (2009 ) Acta Cryst. E65, o3160]. In polymorph II, the six-membered rings form a dihedral angle of 13.8 (1)° [71.6 (1)° in I], and O—H⋯N hydrogen bonds link molecules into chains along [100], whereas the crystal structure of I features hydrogen-bonded centrosymmetric dimers.

Related literature

For details of the synthesis, see: Gao et al. (2004 ). For the crystal structure of polymorph I, see: Zhang et al. (2009).

Experimental

Crystal data

C₁₂H₁₁NO₂
M_r = 201.22
Orthorhombic, P c a 2₁
a = 23.398 (5) Å
b = 5.8343 (12) Å
c = 7.3934 (15) Å
V = 1009.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.50 × 0.37 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.956, T_max = 0.990
8907 measured reflections
2285 independent reflections
1298 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.077
S = 1.01
2285 reflections
138 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 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	1.95	2.763 (2)	173
Symmetry code: (i) $[x+{\script{1\over 2}}, -y, z]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); 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/S1600536812014067/cv5271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014067/cv5271Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014067/cv5271Isup3.cml

checkCIF report

Comment top

The reported here crystal structure of the title compound, C₁₂H₁₁NO₂, represents a new orthorhombic polymorph (II)of the previously reported orthorhombic form (I) (Zhang et al. 2009). It was crystalized from a methanol solution of the title compound and (R)-2-(4-(carboxymethoxy)phenoxy)propanoic acid mixture.

In polymorph II (Figure 1), two six-membered rings form a dihedral angle of 13.8 (1)° [71.6 (1)° in I], and intermolecular O—H···N hydrogen bonds link molecules into chains along [100] (Figure 2, Table 1), in spite of hydrogen-bonded centrosymmetric dimers in polymorph I.

Related literature top

For details of the synthesis, see: Gao et al. (2004). For the crystal structure of polymorph I, see: Zhang et al. (2009).

Experimental top

The 2-(pyridin-4-ylmethoxy)phenol was synthesized by the reaction of o-benzenediol and 4-chloromethylpyridine hydrochloride under nitrogen atmosphere and alkaline condition (Gao et al., 2004). Colourless block crystals were obtained by slow evaporation of a methanol solution (10 mL) containing title compound (0.402 g, 2 mmol) and (R)-2-(4-(carboxymethoxy)phenoxy)propanoic acid (0.48 g, 2 mmol) which only contained the molecules of title compound.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level for non-H atoms.
	Fig. 2. A partial packing view, showing hydrogen-bonded (dashed lines) chain structure along [100].

2-(pyridin-4-ylmethoxy)phenol top

Crystal data top

C₁₂H₁₁NO₂	F(000) = 424
M_r = 201.22	D_x = 1.324 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 5894 reflections
a = 23.398 (5) Å	θ = 3.3–27.5°
b = 5.8343 (12) Å	µ = 0.09 mm⁻¹
c = 7.3934 (15) Å	T = 293 K
V = 1009.3 (4) Å³	Block, colourless
Z = 4	0.50 × 0.37 × 0.11 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2285 independent reflections
Radiation source: fine-focus sealed tube	1298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ω scan	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −30→30
T_min = 0.956, T_max = 0.990	k = −7→7
8907 measured reflections	l = −9→9

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0218P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2285 reflections	Δρ_max = 0.15 e Å⁻³
138 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0028 (6)

Crystal data top

C₁₂H₁₁NO₂	V = 1009.3 (4) Å³
M_r = 201.22	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 23.398 (5) Å	µ = 0.09 mm⁻¹
b = 5.8343 (12) Å	T = 293 K
c = 7.3934 (15) Å	0.50 × 0.37 × 0.11 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2285 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1298 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.990	R_int = 0.066
8907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.077	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
2285 reflections	Δρ_min = −0.14 e Å⁻³
138 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
O1	0.68990 (6)	0.4700 (3)	0.0425 (3)	0.0567 (5)
H1	0.7109	0.3578	0.0381	0.085*
O2	0.46554 (6)	0.1873 (3)	−0.0201 (2)	0.0566 (5)
N1	0.26917 (7)	−0.1195 (3)	0.0264 (3)	0.0488 (5)
C2	0.59170 (9)	0.5453 (4)	0.0842 (3)	0.0442 (6)
H2	0.6014	0.6865	0.1339	0.053*
C8	0.36646 (8)	0.1609 (4)	0.0395 (3)	0.0390 (5)
C7	0.41925 (8)	0.3104 (4)	0.0562 (3)	0.0429 (6)
H7A	0.4137	0.4538	−0.0078	0.052*
H7B	0.4269	0.3444	0.1824	0.052*
C12	0.36737 (9)	−0.0462 (4)	−0.0507 (3)	0.0448 (6)
H12	0.4003	−0.0958	−0.1091	0.054*
C3	0.53418 (9)	0.4830 (4)	0.0713 (3)	0.0461 (6)
H3	0.5057	0.5825	0.1107	0.055*
C4	0.52013 (8)	0.2740 (4)	0.0000 (3)	0.0410 (6)
C1	0.63411 (8)	0.4011 (4)	0.0247 (3)	0.0403 (5)
C6	0.61922 (9)	0.1936 (4)	−0.0516 (4)	0.0518 (6)
H6	0.6475	0.0958	−0.0948	0.062*
C9	0.31568 (9)	0.2274 (4)	0.1199 (3)	0.0463 (6)
H9	0.3132	0.3668	0.1804	0.056*
C10	0.26894 (9)	0.0849 (4)	0.1093 (3)	0.0499 (7)
H10	0.2351	0.1333	0.1629	0.060*
C5	0.56238 (9)	0.1309 (4)	−0.0638 (4)	0.0541 (7)
H5	0.5526	−0.0089	−0.1156	0.065*
C11	0.31825 (8)	−0.1789 (4)	−0.0526 (3)	0.0485 (6)
H11	0.3196	−0.3186	−0.1131	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0343 (8)	0.0535 (11)	0.0821 (13)	−0.0041 (7)	−0.0031 (10)	0.0010 (11)
O2	0.0315 (8)	0.0521 (10)	0.0861 (14)	−0.0023 (7)	0.0054 (9)	−0.0184 (11)
N1	0.0361 (10)	0.0534 (13)	0.0569 (12)	0.0003 (10)	0.0028 (10)	0.0084 (12)
C2	0.0414 (13)	0.0342 (13)	0.0569 (17)	−0.0032 (10)	−0.0020 (12)	−0.0076 (12)
C8	0.0350 (11)	0.0406 (13)	0.0416 (13)	0.0046 (10)	−0.0013 (11)	0.0052 (12)
C7	0.0378 (12)	0.0438 (13)	0.0472 (15)	0.0026 (10)	0.0045 (12)	−0.0016 (14)
C12	0.0333 (12)	0.0500 (15)	0.0510 (14)	0.0030 (11)	0.0049 (12)	0.0009 (14)
C3	0.0413 (13)	0.0392 (14)	0.0577 (16)	0.0057 (11)	0.0009 (13)	−0.0070 (13)
C4	0.0313 (11)	0.0430 (13)	0.0487 (14)	0.0001 (10)	0.0011 (10)	−0.0034 (12)
C1	0.0329 (11)	0.0421 (13)	0.0460 (14)	−0.0004 (10)	0.0000 (12)	0.0045 (13)
C6	0.0375 (12)	0.0489 (15)	0.0690 (17)	0.0089 (11)	0.0008 (14)	−0.0165 (15)
C9	0.0425 (13)	0.0437 (15)	0.0528 (15)	0.0036 (12)	0.0052 (11)	0.0025 (13)
C10	0.0367 (13)	0.0554 (17)	0.0577 (16)	0.0096 (12)	0.0054 (12)	0.0097 (15)
C5	0.0424 (13)	0.0429 (14)	0.0771 (18)	−0.0008 (11)	−0.0026 (14)	−0.0206 (16)
C11	0.0432 (12)	0.0516 (16)	0.0506 (14)	−0.0007 (12)	0.0004 (12)	−0.0006 (14)

Geometric parameters (Å, º) top

O1—C1	1.372 (2)	C12—C11	1.386 (3)
O1—H1	0.8200	C12—H12	0.9300
O2—C4	1.382 (2)	C3—C4	1.368 (3)
O2—C7	1.417 (2)	C3—H3	0.9300
N1—C11	1.334 (3)	C4—C5	1.377 (3)
N1—C10	1.340 (3)	C1—C6	1.380 (3)
C2—C1	1.373 (3)	C6—C5	1.382 (3)
C2—C3	1.397 (3)	C6—H6	0.9300
C2—H2	0.9300	C9—C10	1.376 (3)
C8—C12	1.381 (3)	C9—H9	0.9300
C8—C9	1.384 (3)	C10—H10	0.9300
C8—C7	1.517 (3)	C5—H5	0.9300
C7—H7A	0.9700	C11—H11	0.9300
C7—H7B	0.9700

C1—O1—H1	109.5	C3—C4—C5	119.98 (18)
C4—O2—C7	118.54 (17)	C3—C4—O2	126.16 (19)
C11—N1—C10	115.8 (2)	C5—C4—O2	113.8 (2)
C1—C2—C3	121.0 (2)	O1—C1—C2	118.5 (2)
C1—C2—H2	119.5	O1—C1—C6	122.45 (19)
C3—C2—H2	119.5	C2—C1—C6	119.08 (19)
C12—C8—C9	117.8 (2)	C1—C6—C5	120.1 (2)
C12—C8—C7	122.01 (19)	C1—C6—H6	119.9
C9—C8—C7	120.2 (2)	C5—C6—H6	119.9
O2—C7—C8	107.36 (18)	C10—C9—C8	119.2 (2)
O2—C7—H7A	110.2	C10—C9—H9	120.4
C8—C7—H7A	110.2	C8—C9—H9	120.4
O2—C7—H7B	110.2	N1—C10—C9	124.1 (2)
C8—C7—H7B	110.2	N1—C10—H10	118.0
H7A—C7—H7B	108.5	C9—C10—H10	118.0
C8—C12—C11	118.8 (2)	C4—C5—C6	120.5 (2)
C8—C12—H12	120.6	C4—C5—H5	119.7
C11—C12—H12	120.6	C6—C5—H5	119.7
C4—C3—C2	119.3 (2)	N1—C11—C12	124.4 (2)
C4—C3—H3	120.3	N1—C11—H11	117.8
C2—C3—H3	120.3	C12—C11—H11	117.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.82	1.95	2.763 (2)	173

Symmetry code: (i) x+1/2, −y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁NO₂
M_r	201.22
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	23.398 (5), 5.8343 (12), 7.3934 (15)
V (Å³)	1009.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.37 × 0.11

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.956, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	8907, 2285, 1298
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.077, 1.01
No. of reflections	2285
No. of parameters	138
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), 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	1.95	2.763 (2)	172.5

Symmetry code: (i) x+1/2, −y, z.

Acknowledgements

This work was supported by a grant from the Two-Way Support Programs of Sichuan Agricultural University (project Nos. 00770115 & 00770116).

References

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