(2-Amino-phen-yl)[(5S)-5-hydr-oxy-3,5-dimethyl-4,5-dihydro-1H-pyrazol-1-yl]methanone.

In the mol-ecule of the title compound, C(12)H(15)N(3)O(2), the pyrazole ring is oriented at a dihedral angle of 49.64 (6)° with respect to the benzene ring. Intra-molecular O-H⋯O, N-H⋯O and C-H⋯O inter-actions result in the formation of a trifurcated hydrogen bond. In the crystal structure, inter-molecular N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules, forming a network structure.

Related literature

For general background to the diverse medical potential of pyrazoles and their modified forms, see: Gürsoy et al. (2000 ▶); Lynch & McClenaghan (2005 ▶). For the biological activity of pyrazolopyrimidines, see: Shaabani et al. (2009 ▶). For synthetic procedures for the preparation of the 4,5-dihydro­pyrrazole nucleus bearing various functionalities on the ring, see: Bahreni et al. (2009 ▶); Kumarasinghe et al. (2009 ▶); Liu et al. (2009 ▶); Lynch & McClenaghan (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H15N3O2

M = 233.27

Orthorhombic,

a = 23.5705 (7) Å

b = 11.3547 (4) Å

c = 9.1848 (3) Å

V = 2458.18 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.984

14464 measured reflections

3163 independent reflections

2438 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.04

3163 reflections

165 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026294/hk2735sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026294/hk2735Isup2.hkl

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

C12H15N3O2	F(000) = 992
Mr = 233.27	Dx = 1.261 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3163 reflections
a = 23.5705 (7) Å	θ = 3.0–28.7°
b = 11.3547 (4) Å	µ = 0.09 mm−1
c = 9.1848 (3) Å	T = 296 K
V = 2458.18 (14) Å3	Prism, yellow
Z = 8	0.28 × 0.20 × 0.18 mm

Bruker Kappa APEXII CCD diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 3.0°
ω scans	h = −31→30
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.975, Tmax = 0.984	l = −11→12
14464 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0599P)2 + 0.624P] where P = (Fo2 + 2Fc2)/3
3163 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.05818 (4)	0.11538 (8)	0.14455 (10)	0.0359 (3)
O2	0.00495 (5)	0.31866 (9)	−0.00220 (13)	0.0505 (3)
N1	0.06263 (5)	0.10115 (11)	0.45251 (14)	0.0379 (4)
N2	0.09915 (5)	0.28723 (10)	0.08904 (12)	0.0351 (3)
N3	0.13457 (5)	0.38251 (10)	0.12462 (13)	0.0378 (3)
C1	0.13799 (5)	0.16794 (10)	0.28915 (14)	0.0299 (3)
C2	0.11982 (5)	0.11841 (10)	0.42083 (14)	0.0301 (3)
C3	0.16031 (6)	0.09259 (12)	0.52774 (16)	0.0398 (4)
C4	0.21706 (6)	0.11357 (14)	0.50342 (19)	0.0500 (5)
C5	0.23509 (6)	0.16073 (16)	0.3730 (2)	0.0536 (5)
C6	0.19585 (5)	0.18704 (13)	0.26614 (17)	0.0418 (4)
C7	0.09593 (5)	0.18893 (11)	0.17072 (13)	0.0294 (3)
C8	0.06207 (6)	0.31127 (13)	−0.04089 (15)	0.0395 (4)
C9	0.08216 (7)	0.43582 (15)	−0.08055 (19)	0.0521 (5)
C10	0.12563 (6)	0.46354 (12)	0.03036 (16)	0.0401 (4)
C11	0.15629 (9)	0.57783 (15)	0.0355 (2)	0.0616 (6)
C12	0.07320 (8)	0.22171 (17)	−0.15852 (18)	0.0565 (6)
H1A	0.0417 (7)	0.0897 (15)	0.376 (2)	0.0454*
H1B	0.0558 (7)	0.0465 (16)	0.520 (2)	0.0454*
H2	−0.00781	0.25221	0.00998	0.0606*
H3	0.14873	0.06089	0.61624	0.047 (4)*
H4	0.24343	0.09581	0.57548	0.058 (5)*
H5	0.27347	0.17474	0.35709	0.065 (5)*
H6	0.20811	0.21786	0.17776	0.046 (4)*
H9A	0.05099	0.49149	−0.07606	0.0624*
H9B	0.09834	0.43743	−0.17763	0.0624*
H11A	0.18200	0.57798	0.11659	0.0924*
H11B	0.17722	0.58855	−0.05315	0.0924*
H11C	0.12945	0.64081	0.04652	0.0924*
H12A	0.05694	0.24852	−0.24844	0.0848*
H12B	0.11338	0.21170	−0.17043	0.0848*
H12C	0.05638	0.14785	−0.13165	0.0848*

	U11	U22	U33	U12	U13	U23
O1	0.0378 (5)	0.0361 (5)	0.0338 (5)	−0.0054 (4)	−0.0037 (4)	−0.0016 (4)
O2	0.0426 (5)	0.0468 (6)	0.0621 (7)	0.0037 (4)	−0.0006 (5)	0.0086 (5)
N1	0.0352 (6)	0.0442 (7)	0.0342 (6)	−0.0015 (5)	−0.0001 (4)	0.0097 (5)
N2	0.0418 (6)	0.0332 (5)	0.0303 (6)	−0.0038 (4)	−0.0047 (4)	0.0028 (5)
N3	0.0469 (6)	0.0309 (5)	0.0357 (6)	−0.0048 (4)	0.0010 (5)	−0.0009 (5)
C1	0.0318 (6)	0.0255 (5)	0.0325 (7)	0.0012 (4)	−0.0017 (5)	−0.0014 (5)
C2	0.0334 (6)	0.0232 (5)	0.0337 (7)	0.0022 (4)	−0.0022 (5)	−0.0013 (5)
C3	0.0456 (7)	0.0372 (7)	0.0365 (7)	0.0037 (5)	−0.0085 (6)	0.0047 (6)
C4	0.0417 (8)	0.0535 (9)	0.0549 (10)	0.0050 (6)	−0.0177 (7)	0.0016 (7)
C5	0.0308 (7)	0.0637 (10)	0.0662 (11)	−0.0003 (7)	−0.0051 (7)	0.0003 (9)
C6	0.0345 (6)	0.0464 (8)	0.0444 (8)	−0.0019 (5)	0.0035 (6)	0.0020 (6)
C7	0.0325 (5)	0.0290 (6)	0.0266 (6)	0.0018 (4)	0.0025 (4)	−0.0023 (5)
C8	0.0427 (7)	0.0426 (7)	0.0331 (7)	0.0011 (5)	−0.0046 (5)	0.0088 (6)
C9	0.0589 (9)	0.0494 (9)	0.0479 (9)	−0.0038 (7)	−0.0038 (7)	0.0177 (7)
C10	0.0480 (7)	0.0343 (7)	0.0380 (7)	0.0001 (5)	0.0079 (6)	0.0024 (6)
C11	0.0822 (12)	0.0384 (8)	0.0642 (11)	−0.0139 (8)	0.0031 (10)	0.0090 (8)
C12	0.0705 (10)	0.0657 (11)	0.0334 (8)	0.0035 (9)	−0.0054 (7)	−0.0011 (8)

O1—C7	1.2438 (15)	C8—C9	1.535 (2)
O2—C8	1.3950 (18)	C8—C12	1.507 (2)
O2—H2	0.8200	C9—C10	1.479 (2)
N1—C2	1.3929 (17)	C10—C11	1.486 (2)
N2—C7	1.3470 (17)	C3—H3	0.9300
N2—C8	1.5042 (18)	C4—H4	0.9300
N2—N3	1.4051 (16)	C5—H5	0.9300
N3—C10	1.2808 (18)	C6—H6	0.9300
N1—H1B	0.892 (18)	C9—H9A	0.9700
N1—H1A	0.868 (18)	C9—H9B	0.9700
C1—C2	1.4009 (18)	C11—H11A	0.9600
C1—C6	1.3970 (17)	C11—H11B	0.9600
C1—C7	1.4909 (17)	C11—H11C	0.9600
C2—C3	1.4004 (19)	C12—H12A	0.9600
C3—C4	1.377 (2)	C12—H12B	0.9600
C4—C5	1.379 (2)	C12—H12C	0.9600
C5—C6	1.381 (2)
O1···O2	2.9527 (14)	C11···H9Bvii	2.9700
O1···N1	2.8351 (16)	H1A···O1	2.181 (18)
O1···C12	3.0548 (19)	H1A···C7	2.541 (18)
O1···N1i	2.9882 (15)	H1A···O1i	2.380 (17)
O1···N1ii	3.0277 (16)	H1A···H2i	2.2700
O2···N1i	2.9741 (16)	H1B···H3	2.3700
O2···O1	2.9527 (14)	H1B···O1v	2.166 (18)
O1···H1Ai	2.380 (17)	H2···O1	2.5200
O1···H12C	2.5600	H2···C7	2.9500
O1···H1Bii	2.166 (18)	H2···H12C	2.3200
O1···H1A	2.181 (18)	H2···N1i	2.1700
O1···H2	2.5200	H2···H1Ai	2.2700
O2···H12Aiii	2.8300	H3···H1B	2.3700
O2···H9Aiv	2.6300	H3···C1v	3.0600
N1···O1	2.8351 (16)	H4···N3viii	2.9200
N1···O1i	2.9882 (15)	H4···C11viii	3.1000
N1···O2i	2.9741 (16)	H4···H6viii	2.5800
N1···O1v	3.0277 (16)	H6···N2	2.8100
N3···C6	2.9499 (18)	H6···N3	2.6000
N1···H2i	2.1700	H6···C4vi	3.0600
N1···H12Cv	2.9300	H6···H4vi	2.5800
N2···H6	2.8100	H9A···O2iv	2.6300
N3···H6	2.6000	H9B···H12A	2.4400
N3···H4vi	2.9200	H9B···H12B	2.5900
N3···H9Bvii	2.8700	H9B···N3ix	2.8700
C6···N3	2.9499 (18)	H9B···C10ix	2.9800
C12···O1	3.0548 (19)	H9B···C11ix	2.9700
C1···H3ii	3.0600	H11B···C6ix	3.0700
C2···H11Cvii	2.9800	H11C···C2ix	2.9800
C4···H6viii	3.0600	H12A···H9B	2.4400
C6···H11Bvii	3.0700	H12A···O2iii	2.8300
C7···H2	2.9500	H12B···H9B	2.5900
C7···H12C	2.9700	H12C···O1	2.5600
C7···H1A	2.541 (18)	H12C···C7	2.9700
C10···H9Bvii	2.9800	H12C···H2	2.3200
C11···H4vi	3.1000	H12C···N1ii	2.9300
C8—O2—H2	109.00	N3—C10—C11	121.72 (14)
N3—N2—C7	122.82 (11)	C9—C10—C11	123.00 (14)
N3—N2—C8	112.96 (10)	N3—C10—C9	115.26 (13)
C7—N2—C8	124.02 (11)	C2—C3—H3	120.00
N2—N3—C10	107.35 (11)	C4—C3—H3	120.00
C2—N1—H1B	114.7 (11)	C3—C4—H4	120.00
C2—N1—H1A	113.7 (12)	C5—C4—H4	120.00
H1A—N1—H1B	110.8 (16)	C4—C5—H5	120.00
C2—C1—C6	119.43 (12)	C6—C5—H5	120.00
C2—C1—C7	119.39 (10)	C1—C6—H6	120.00
C6—C1—C7	120.93 (12)	C5—C6—H6	120.00
N1—C2—C1	122.19 (11)	C8—C9—H9A	111.00
C1—C2—C3	118.76 (11)	C8—C9—H9B	111.00
N1—C2—C3	118.92 (12)	C10—C9—H9A	111.00
C2—C3—C4	120.80 (14)	C10—C9—H9B	111.00
C3—C4—C5	120.49 (14)	H9A—C9—H9B	109.00
C4—C5—C6	119.66 (13)	C10—C11—H11A	109.00
C1—C6—C5	120.84 (14)	C10—C11—H11B	109.00
N2—C7—C1	120.09 (11)	C10—C11—H11C	109.00
O1—C7—N2	119.28 (11)	H11A—C11—H11B	109.00
O1—C7—C1	120.62 (11)	H11A—C11—H11C	109.00
O2—C8—C9	107.62 (12)	H11B—C11—H11C	109.00
O2—C8—C12	113.04 (13)	C8—C12—H12A	109.00
O2—C8—N2	111.69 (11)	C8—C12—H12B	109.00
N2—C8—C9	100.15 (11)	C8—C12—H12C	109.00
N2—C8—C12	110.20 (12)	H12A—C12—H12B	109.00
C9—C8—C12	113.45 (13)	H12A—C12—H12C	109.00
C8—C9—C10	104.26 (13)	H12B—C12—H12C	109.00
C7—N2—N3—C10	−176.72 (12)	C7—C1—C2—C3	176.17 (11)
C8—N2—N3—C10	−1.71 (15)	C2—C1—C6—C5	−1.8 (2)
N3—N2—C7—O1	170.03 (11)	C7—C1—C6—C5	−176.01 (14)
N3—N2—C7—C1	−11.16 (18)	C2—C1—C7—O1	−40.35 (17)
C8—N2—C7—O1	−4.42 (19)	C2—C1—C7—N2	140.86 (12)
C8—N2—C7—C1	174.39 (11)	C6—C1—C7—O1	133.87 (13)
N3—N2—C8—O2	−112.23 (12)	C6—C1—C7—N2	−44.92 (17)
N3—N2—C8—C9	1.48 (14)	N1—C2—C3—C4	−176.93 (13)
N3—N2—C8—C12	121.25 (13)	C1—C2—C3—C4	−1.1 (2)
C7—N2—C8—O2	62.70 (16)	C2—C3—C4—C5	0.1 (2)
C7—N2—C8—C9	176.42 (12)	C3—C4—C5—C6	0.0 (2)
C7—N2—C8—C12	−63.81 (17)	C4—C5—C6—C1	0.9 (2)
N2—N3—C10—C9	1.18 (17)	O2—C8—C9—C10	116.07 (13)
N2—N3—C10—C11	179.96 (13)	N2—C8—C9—C10	−0.73 (14)
C6—C1—C2—N1	177.60 (12)	C12—C8—C9—C10	−118.11 (14)
C6—C1—C2—C3	1.86 (18)	C8—C9—C10—N3	−0.24 (18)
C7—C1—C2—N1	−8.09 (18)	C8—C9—C10—C11	−179.00 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.868 (18)	2.181 (18)	2.8351 (16)	131.9 (15)
N1—H1A···O1i	0.868 (18)	2.380 (17)	2.9882 (15)	127.4 (15)
N1—H1B···O1v	0.892 (18)	2.166 (18)	3.0277 (16)	162.4 (16)
O2—H2···O1	0.82	2.52	2.9527 (14)	114
O2—H2···N1i	0.82	2.17	2.9741 (16)	165
C6—H6···N3	0.93	2.60	2.9499 (18)	103
C12—H12C···O1	0.96	2.56	3.0548 (19)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.868 (18)	2.181 (18)	2.8351 (16)	131.9 (15)
N1—H1A⋯O1i	0.868 (18)	2.380 (17)	2.9882 (15)	127.4 (15)
N1—H1B⋯O1ii	0.892 (18)	2.166 (18)	3.0277 (16)	162.4 (16)
O2—H2⋯O1	0.82	2.52	2.9527 (14)	114
O2—H2⋯N1i	0.82	2.17	2.9741 (16)	165
C6—H6⋯N3	0.93	2.60	2.9499 (18)	103
C12—H12C⋯O1	0.96	2.56	3.0548 (19)	112

Symmetry codes: (i) ; (ii) .