5-Methoxy-methyl-4-phen-oxy-1H-pyrazol-3-ol.

In the title compound, C(11)H(12)N(2)O(3), the pyrazole ring system is essentially planar [maximum deviation = 0.002 (2) Å] and forms a dihedral angle of 66.93 (9)° with the benzene ring. In the crystal packing, pairs of inter-molecular N-H⋯O and O-H⋯N hydrogen bonds connect neighbouring mol-ecules into dimers, generating R(2) (2)(10) and R(2) (2)(8) ring motifs, respectively. The crystal structure is further stabilized by C-H⋯π inter-actions.

Related literature

For the biological activity of pyrazoles, see: Genin et al. (2000 ▶); Hsu et al. (1956 ▶); Jung et al. (2002 ▶); Kudo et al. (1999 ▶); Singh et al. (1978 ▶); Skipper et al. (1955 ▶); Storer et al. (1999 ▶); Tewari & Mishra (2001 ▶). For pyrazole derivatives, see: Baraldi et al. (2003 ▶); Brown et al. (2004 ▶); Duma et al. (2000 ▶); Heerding (2003 ▶); Qiao et al. (2003 ▶); Stamford & Wu (2004 ▶). For a related structure, see: Goh et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H12N2O3

M = 220.23

Monoclinic,

a = 8.8876 (5) Å

b = 10.3031 (5) Å

c = 12.0083 (6) Å

β = 100.917 (3)°

V = 1079.7 (1) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.69 × 0.57 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.934, T max = 0.983

14470 measured reflections

3433 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.138

S = 1.10

3433 reflections

193 parameters

All H-atom parameters refined

Δρmax = 0.45 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050302/lh2960sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050302/lh2960Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H12N2O3	F(000) = 464
Mr = 220.23	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6087 reflections
a = 8.8876 (5) Å	θ = 2.3–32.2°
b = 10.3031 (5) Å	µ = 0.10 mm−1
c = 12.0083 (6) Å	T = 100 K
β = 100.917 (3)°	Plate, yellow
V = 1079.7 (1) Å3	0.69 × 0.57 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3433 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 31.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→11
Tmin = 0.934, Tmax = 0.983	k = −14→14
14470 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	All H-atom parameters refined
S = 1.10	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.7446P] where P = (Fo2 + 2Fc2)/3
3433 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.79382 (13)	0.20467 (12)	0.25817 (9)	0.0209 (3)
O2	0.84461 (13)	0.54359 (11)	0.06550 (11)	0.0243 (3)
O3	0.86330 (14)	−0.01790 (11)	0.10686 (10)	0.0210 (3)
N1	0.97188 (15)	0.15166 (12)	0.01762 (11)	0.0187 (3)
N2	0.98156 (16)	0.28291 (13)	0.03420 (12)	0.0197 (3)
C1	0.5751 (2)	0.2793 (2)	0.32287 (16)	0.0313 (4)
C2	0.4180 (2)	0.2854 (2)	0.31444 (19)	0.0373 (5)
C3	0.3212 (2)	0.2243 (2)	0.22663 (17)	0.0315 (4)
C4	0.3817 (2)	0.1569 (2)	0.14638 (17)	0.0339 (4)
C5	0.5396 (2)	0.1508 (2)	0.15308 (16)	0.0293 (4)
C6	0.63487 (18)	0.21173 (15)	0.24200 (13)	0.0182 (3)
C7	0.85883 (17)	0.21114 (15)	0.16285 (13)	0.0178 (3)
C8	0.91537 (18)	0.32155 (15)	0.12032 (13)	0.0188 (3)
C9	0.9123 (2)	0.46065 (16)	0.15618 (14)	0.0222 (3)
C10	0.6866 (2)	0.51602 (19)	0.02363 (19)	0.0310 (4)
C11	0.89717 (17)	0.10779 (15)	0.09653 (13)	0.0177 (3)
H1A	0.644 (3)	0.324 (2)	0.3821 (19)	0.042 (6)*
H2A	0.375 (3)	0.334 (3)	0.368 (2)	0.056 (8)*
H3A	0.214 (3)	0.227 (2)	0.2222 (19)	0.039 (6)*
H4A	0.315 (3)	0.112 (3)	0.087 (2)	0.050 (7)*
H5A	0.583 (2)	0.106 (2)	0.0976 (18)	0.033 (6)*
H9A	1.017 (2)	0.4927 (19)	0.1791 (16)	0.021 (5)*
H9B	0.853 (2)	0.466 (2)	0.2184 (17)	0.028 (5)*
H10A	0.678 (2)	0.428 (2)	−0.0107 (19)	0.038 (6)*
H10B	0.652 (3)	0.582 (3)	−0.032 (2)	0.047 (7)*
H10C	0.625 (3)	0.518 (2)	0.088 (2)	0.041 (6)*
H1N2	1.038 (2)	0.329 (2)	−0.0073 (17)	0.024 (5)*
H1O3	0.924 (3)	−0.065 (2)	0.067 (2)	0.047 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0193 (5)	0.0261 (6)	0.0184 (5)	0.0006 (5)	0.0062 (4)	−0.0018 (4)
O2	0.0232 (6)	0.0139 (6)	0.0362 (7)	−0.0005 (4)	0.0070 (5)	0.0036 (5)
O3	0.0265 (6)	0.0133 (5)	0.0264 (6)	−0.0028 (5)	0.0134 (5)	−0.0010 (4)
N1	0.0228 (7)	0.0116 (6)	0.0232 (6)	0.0002 (5)	0.0081 (5)	0.0000 (5)
N2	0.0233 (7)	0.0131 (6)	0.0246 (7)	−0.0006 (5)	0.0091 (5)	0.0009 (5)
C1	0.0302 (9)	0.0340 (11)	0.0320 (9)	−0.0006 (8)	0.0114 (7)	−0.0121 (8)
C2	0.0321 (10)	0.0416 (12)	0.0431 (11)	0.0074 (9)	0.0194 (9)	−0.0070 (9)
C3	0.0215 (8)	0.0372 (11)	0.0378 (10)	0.0046 (8)	0.0110 (7)	0.0117 (8)
C4	0.0228 (9)	0.0446 (12)	0.0332 (10)	−0.0023 (8)	0.0027 (7)	−0.0019 (9)
C5	0.0236 (9)	0.0364 (11)	0.0286 (9)	0.0012 (7)	0.0065 (7)	−0.0094 (8)
C6	0.0198 (7)	0.0143 (7)	0.0220 (7)	0.0012 (6)	0.0080 (6)	0.0024 (6)
C7	0.0187 (7)	0.0175 (7)	0.0178 (7)	0.0007 (6)	0.0051 (5)	−0.0002 (6)
C8	0.0191 (7)	0.0154 (7)	0.0218 (7)	0.0013 (6)	0.0038 (6)	−0.0012 (6)
C9	0.0254 (8)	0.0153 (8)	0.0263 (8)	0.0004 (6)	0.0056 (6)	−0.0022 (6)
C10	0.0238 (9)	0.0213 (9)	0.0462 (11)	0.0011 (7)	0.0020 (8)	0.0031 (8)
C11	0.0181 (7)	0.0159 (7)	0.0198 (7)	−0.0007 (6)	0.0054 (5)	0.0001 (6)

O1—C7	1.3781 (18)	C3—C4	1.377 (3)
O1—C6	1.3910 (19)	C3—H3A	0.94 (2)
O2—C9	1.425 (2)	C4—C5	1.392 (3)
O2—C10	1.427 (2)	C4—H4A	0.96 (3)
O3—C11	1.3406 (19)	C5—C6	1.382 (2)
O3—H1O3	0.92 (3)	C5—H5A	0.95 (2)
N1—C11	1.335 (2)	C7—C8	1.380 (2)
N1—N2	1.3672 (19)	C7—C11	1.410 (2)
N2—C8	1.343 (2)	C8—C9	1.498 (2)
N2—H1N2	0.91 (2)	C9—H9A	0.98 (2)
C1—C6	1.380 (2)	C9—H9B	0.99 (2)
C1—C2	1.383 (3)	C10—H10A	0.99 (2)
C1—H1A	0.96 (2)	C10—H10B	0.96 (3)
C2—C3	1.380 (3)	C10—H10C	1.03 (2)
C2—H2A	0.95 (3)
C7—O1—C6	117.13 (12)	C1—C6—O1	116.36 (15)
C9—O2—C10	113.24 (13)	C5—C6—O1	122.80 (14)
C11—O3—H1O3	107.0 (15)	O1—C7—C8	125.92 (14)
C11—N1—N2	104.93 (13)	O1—C7—C11	128.09 (14)
C8—N2—N1	112.37 (13)	C8—C7—C11	105.64 (14)
C8—N2—H1N2	129.8 (13)	N2—C8—C7	106.50 (14)
N1—N2—H1N2	117.5 (13)	N2—C8—C9	122.63 (14)
C6—C1—C2	119.29 (18)	C7—C8—C9	130.87 (15)
C6—C1—H1A	119.0 (14)	O2—C9—C8	112.47 (13)
C2—C1—H1A	121.7 (14)	O2—C9—H9A	104.7 (11)
C3—C2—C1	120.65 (18)	C8—C9—H9A	109.7 (11)
C3—C2—H2A	119.0 (16)	O2—C9—H9B	109.6 (12)
C1—C2—H2A	120.3 (16)	C8—C9—H9B	107.9 (12)
C4—C3—C2	119.72 (17)	H9A—C9—H9B	112.5 (16)
C4—C3—H3A	119.8 (14)	O2—C10—H10A	108.6 (13)
C2—C3—H3A	120.5 (14)	O2—C10—H10B	105.4 (14)
C3—C4—C5	120.34 (18)	H10A—C10—H10B	111.7 (19)
C3—C4—H4A	119.9 (15)	O2—C10—H10C	111.1 (13)
C5—C4—H4A	119.7 (15)	H10A—C10—H10C	108.8 (18)
C6—C5—C4	119.20 (17)	H10B—C10—H10C	111.3 (19)
C6—C5—H5A	119.6 (13)	N1—C11—O3	122.92 (14)
C4—C5—H5A	121.2 (13)	N1—C11—C7	110.57 (14)
C1—C6—C5	120.79 (16)	O3—C11—C7	126.51 (14)
C11—N1—N2—C8	−0.09 (17)	N1—N2—C8—C9	179.33 (14)
C6—C1—C2—C3	0.3 (3)	O1—C7—C8—N2	173.96 (14)
C1—C2—C3—C4	−0.2 (3)	C11—C7—C8—N2	0.26 (17)
C2—C3—C4—C5	−0.4 (3)	O1—C7—C8—C9	−5.4 (3)
C3—C4—C5—C6	0.9 (3)	C11—C7—C8—C9	−179.12 (16)
C2—C1—C6—C5	0.2 (3)	C10—O2—C9—C8	64.02 (19)
C2—C1—C6—O1	−177.32 (17)	N2—C8—C9—O2	56.1 (2)
C4—C5—C6—C1	−0.7 (3)	C7—C8—C9—O2	−124.58 (18)
C4—C5—C6—O1	176.57 (17)	N2—N1—C11—O3	179.16 (14)
C7—O1—C6—C1	−142.80 (16)	N2—N1—C11—C7	0.26 (17)
C7—O1—C6—C5	39.8 (2)	O1—C7—C11—N1	−173.85 (14)
C6—O1—C7—C8	95.50 (18)	C8—C7—C11—N1	−0.33 (18)
C6—O1—C7—C11	−92.22 (19)	O1—C7—C11—O3	7.3 (3)
N1—N2—C8—C7	−0.12 (18)	C8—C7—C11—O3	−179.19 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.91 (2)	1.89 (2)	2.7778 (18)	165.7 (19)
O3—H1O3···N1ii	0.92 (2)	1.74 (2)	2.6663 (18)	176 (2)
C3—H3A···Cg1iii	0.94 (2)	2.77 (3)	2.73	147.6 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.91 (2)	1.89 (2)	2.7778 (18)	165.7 (19)
O3—H1O3⋯N1ii	0.92 (2)	1.74 (2)	2.6663 (18)	176 (2)
C3—H3A⋯Cg1iii	0.94 (2)	2.77 (3)	2.73	147.6 (18)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 benzene ring.