5-(2-Hy-droxy-phen-yl)-3-methyl-4,5-di-hydro-1H-pyrazole-1-carbaldehyde.

In the title compound, C(11)H(12)N(2)O(2), the dihydro-pyrazole and benzene rings are oriented at a dihedral angle of 68.35 (5)°. The dihydro-pyrazole ring is planar, with a mean deviation from the mean plane of 0.0409 Å. The crystal structure is stabilized by O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the anti­bacterial bioactivity of pyrazole derivatives, see: Bekhita & Abdel-Aziem (2004 ▶); Tanitame et al. (2004a ▶,b ▶). For the biological properties of dihydro­n class="Chemical">pyrazole derivatives, see: Dmytro et al. (2009 ▶); Need et al. (2006 ▶).

Experimental

Crystal data

C11H12N2O2

M = 204.23

Monoclinic,

a = 7.3835 (15) Å

b = 13.454 (3) Å

c = 10.507 (2) Å

β = 106.46 (3)°

V = 1001.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.21 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.980, T max = 0.990

5606 measured reflections

1957 independent reflections

1579 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.08

1957 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031600/ez2216sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031600/ez2216Isup2.hkl

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

C11H12N2O2	F(000) = 432
Mr = 204.23	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3835 (15) Å	Cell parameters from 972 reflections
b = 13.454 (3) Å	θ = 3.5–24.7°
c = 10.507 (2) Å	µ = 0.10 mm−1
β = 106.46 (3)°	T = 293 K
V = 1001.0 (3) Å3	Block, colorless
Z = 4	0.21 × 0.16 × 0.11 mm

Bruker Smart APEX CCD area-detector diffractometer	1957 independent reflections
Radiation source: fine-focus sealed tube	1579 reflections with I > 2σ(I)
graphite	Rint = 0.019
phi and ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.980, Tmax = 0.990	k = −16→13
5606 measured reflections	l = −12→12

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) = 0.086	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.0583P] where P = (Fo2 + 2Fc2)/3
1957 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
C1	0.71057 (17)	0.62387 (9)	0.66395 (12)	0.0271 (3)
H1	0.6378	0.6593	0.5914	0.032*
C2	0.81434 (16)	0.41527 (9)	0.51386 (12)	0.0253 (3)
C3	0.7931 (2)	0.35621 (10)	0.39114 (13)	0.0350 (3)
H3A	0.7264	0.2958	0.3963	0.052*
H3B	0.9157	0.3406	0.3820	0.052*
H3C	0.7235	0.3941	0.3157	0.052*
C4	0.93391 (17)	0.38472 (9)	0.64868 (12)	0.0260 (3)
H4A	1.0670	0.3859	0.6534	0.031*
H4B	0.9004	0.3187	0.6715	0.031*
C5	0.88677 (16)	0.46406 (8)	0.74008 (11)	0.0225 (3)
H5	1.0031	0.4963	0.7925	0.027*
C6	0.77821 (16)	0.42376 (8)	0.83124 (11)	0.0215 (3)
C7	0.58407 (17)	0.42893 (9)	0.80332 (12)	0.0284 (3)
H7	0.5137	0.4564	0.7234	0.034*
C8	0.49282 (18)	0.39382 (10)	0.89242 (14)	0.0341 (3)
H8	0.3621	0.3985	0.8730	0.041*
C9	0.59650 (18)	0.35179 (10)	1.01025 (13)	0.0320 (3)
H9	0.5357	0.3294	1.0712	0.038*
C10	0.78979 (18)	0.34274 (9)	1.03825 (12)	0.0276 (3)
H10	0.8587	0.3126	1.1167	0.033*
C11	0.88131 (16)	0.37877 (8)	0.94901 (11)	0.0221 (3)
N1	0.77351 (14)	0.53492 (7)	0.64102 (9)	0.0237 (2)
N2	0.72976 (14)	0.49870 (8)	0.51056 (9)	0.0259 (3)
O1	0.74131 (13)	0.66270 (6)	0.77367 (9)	0.0335 (2)
O2	1.07147 (12)	0.37142 (7)	0.97002 (8)	0.0306 (2)
H2	1.1227	0.3625	1.0493	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0288 (6)	0.0248 (7)	0.0264 (7)	0.0022 (5)	0.0059 (5)	0.0068 (5)
C2	0.0238 (6)	0.0293 (7)	0.0251 (6)	−0.0015 (5)	0.0107 (5)	0.0023 (5)
C3	0.0377 (7)	0.0404 (8)	0.0272 (7)	0.0047 (6)	0.0099 (6)	−0.0024 (6)
C4	0.0282 (6)	0.0268 (7)	0.0248 (6)	0.0030 (5)	0.0104 (5)	0.0037 (5)
C5	0.0231 (6)	0.0216 (6)	0.0219 (6)	0.0008 (5)	0.0049 (5)	0.0044 (5)
C6	0.0266 (6)	0.0175 (6)	0.0208 (6)	−0.0009 (5)	0.0073 (5)	−0.0007 (4)
C7	0.0262 (6)	0.0293 (7)	0.0282 (7)	−0.0012 (5)	0.0051 (5)	0.0045 (5)
C8	0.0249 (6)	0.0382 (8)	0.0407 (8)	−0.0045 (5)	0.0117 (6)	0.0015 (6)
C9	0.0383 (7)	0.0324 (7)	0.0306 (7)	−0.0097 (6)	0.0183 (6)	−0.0016 (5)
C10	0.0383 (7)	0.0248 (7)	0.0203 (6)	−0.0020 (5)	0.0092 (5)	0.0012 (5)
C11	0.0264 (6)	0.0184 (6)	0.0218 (6)	0.0009 (5)	0.0074 (5)	−0.0028 (5)
N1	0.0286 (5)	0.0233 (5)	0.0188 (5)	0.0018 (4)	0.0059 (4)	0.0037 (4)
N2	0.0275 (5)	0.0306 (6)	0.0200 (5)	0.0001 (4)	0.0072 (4)	0.0026 (4)
O1	0.0418 (5)	0.0275 (5)	0.0279 (5)	0.0067 (4)	0.0047 (4)	−0.0002 (4)
O2	0.0267 (5)	0.0416 (6)	0.0228 (4)	0.0073 (4)	0.0059 (3)	0.0066 (4)

C1—O1	1.2269 (15)	C5—H5	0.9800
C1—N1	1.3303 (16)	C6—C7	1.3811 (17)
C1—H1	0.9300	C6—C11	1.3940 (16)
C2—N2	1.2802 (16)	C7—C8	1.3824 (19)
C2—C3	1.4846 (18)	C7—H7	0.9300
C2—C4	1.4988 (17)	C8—C9	1.3790 (19)
C3—H3A	0.9600	C8—H8	0.9300
C3—H3B	0.9600	C9—C10	1.3785 (18)
C3—H3C	0.9600	C9—H9	0.9300
C4—C5	1.5403 (17)	C10—C11	1.3892 (18)
C4—H4A	0.9700	C10—H10	0.9300
C4—H4B	0.9700	C11—O2	1.3617 (15)
C5—N1	1.4828 (14)	N1—N2	1.4034 (14)
C5—C6	1.5129 (17)	O2—H2	0.8200
O1—C1—N1	124.90 (11)	C7—C6—C11	118.90 (12)
O1—C1—H1	117.5	C7—C6—C5	123.48 (11)
N1—C1—H1	117.5	C11—C6—C5	117.62 (11)
N2—C2—C3	121.01 (11)	C6—C7—C8	120.97 (12)
N2—C2—C4	114.73 (11)	C6—C7—H7	119.5
C3—C2—C4	124.26 (11)	C8—C7—H7	119.5
C2—C3—H3A	109.5	C9—C8—C7	119.67 (12)
C2—C3—H3B	109.5	C9—C8—H8	120.2
H3A—C3—H3B	109.5	C7—C8—H8	120.2
C2—C3—H3C	109.5	C10—C9—C8	120.38 (13)
H3A—C3—H3C	109.5	C10—C9—H9	119.8
H3B—C3—H3C	109.5	C8—C9—H9	119.8
C2—C4—C5	102.86 (9)	C9—C10—C11	119.81 (12)
C2—C4—H4A	111.2	C9—C10—H10	120.1
C5—C4—H4A	111.2	C11—C10—H10	120.1
C2—C4—H4B	111.2	O2—C11—C10	122.79 (11)
C5—C4—H4B	111.2	O2—C11—C6	117.01 (11)
H4A—C4—H4B	109.1	C10—C11—C6	120.20 (11)
N1—C5—C6	112.35 (10)	C1—N1—N2	119.59 (9)
N1—C5—C4	100.95 (9)	C1—N1—C5	127.43 (10)
C6—C5—C4	113.59 (10)	N2—N1—C5	112.98 (9)
N1—C5—H5	109.9	C2—N2—N1	107.61 (9)
C6—C5—H5	109.9	C11—O2—H2	109.5
C4—C5—H5	109.9
N2—C2—C4—C5	7.20 (14)	C7—C6—C11—O2	177.26 (11)
C3—C2—C4—C5	−173.35 (11)	C5—C6—C11—O2	−2.42 (15)
C2—C4—C5—N1	−8.69 (12)	C7—C6—C11—C10	−2.02 (17)
C2—C4—C5—C6	111.79 (11)	C5—C6—C11—C10	178.30 (10)
N1—C5—C6—C7	17.36 (16)	O1—C1—N1—N2	−179.59 (11)
C4—C5—C6—C7	−96.46 (14)	O1—C1—N1—C5	1.7 (2)
N1—C5—C6—C11	−162.98 (10)	C6—C5—N1—C1	66.03 (15)
C4—C5—C6—C11	83.21 (13)	C4—C5—N1—C1	−172.61 (11)
C11—C6—C7—C8	2.53 (19)	C6—C5—N1—N2	−112.71 (11)
C5—C6—C7—C8	−177.80 (12)	C4—C5—N1—N2	8.64 (12)
C6—C7—C8—C9	−0.9 (2)	C3—C2—N2—N1	178.62 (11)
C7—C8—C9—C10	−1.4 (2)	C4—C2—N2—N1	−1.92 (14)
C8—C9—C10—C11	1.87 (19)	C1—N1—N2—C2	176.47 (11)
C9—C10—C11—O2	−179.39 (11)	C5—N1—N2—C2	−4.68 (13)
C9—C10—C11—C6	−0.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.88	2.6954 (14)	175.
C4—H4B···O1ii	0.97	2.48	3.4438 (16)	170.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.88	2.6954 (14)	175
C4—H4B⋯O1ii	0.97	2.48	3.4438 (16)	170

Symmetry codes: (i) ; (ii) .