(5-Hy-droxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone monohydrate.

In the title compound, C(16)H(15)N(3)O(2)·H(2)O, the mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0474 (18) Å] makes dihedral angles of 86.32 (11) and 45.04 (10)° with the phenyl and pyridine rings, respectively. The dihedral angle between the phenyl and pyridine rings is 69.62 (11)°. In the crystal, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds connect the components into chains along [010]. The crystal structure is further stabilized by π-π stacking inter-actions with centroid-centroid distances of 3.7730 (12) Å.

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H15N3O2·H2O

M = 299.33

Monoclinic,

a = 16.9676 (10) Å

b = 7.0266 (5) Å

c = 12.6135 (6) Å

β = 93.004 (3)°

V = 1501.77 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.971, T max = 0.983

8525 measured reflections

3059 independent reflections

1916 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.121

S = 1.03

3059 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 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 and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005275X/lh5187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005275X/lh5187Isup2.hkl

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

C16H15N3O2·H2O	F(000) = 632
Mr = 299.33	Dx = 1.324 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2540 reflections
a = 16.9676 (10) Å	θ = 2.5–27.5°
b = 7.0266 (5) Å	µ = 0.09 mm−1
c = 12.6135 (6) Å	T = 296 K
β = 93.004 (3)°	Prism, white
V = 1501.77 (16) Å3	0.32 × 0.24 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3059 independent reflections
Radiation source: fine-focus sealed tube	1916 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→21
Tmin = 0.971, Tmax = 0.983	k = −7→8
8525 measured reflections	l = −15→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
3059 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.32045 (8)	0.3424 (2)	−0.01490 (10)	0.0461 (4)
H1	0.2849	0.2478	−0.0322	0.069*
O2	0.22503 (8)	0.70361 (19)	0.00147 (10)	0.0455 (4)
O1W	0.21323 (8)	0.4293 (2)	0.41563 (10)	0.0522 (4)
H1W1	0.2123	0.5449	0.4498	0.078*
H2W1	0.1656	0.3911	0.4143	0.078*
N1	0.17899 (8)	0.3038 (2)	0.15669 (11)	0.0339 (4)
N2	0.22186 (8)	0.4400 (2)	0.10150 (11)	0.0347 (4)
N3	−0.05005 (9)	0.7733 (2)	0.10396 (13)	0.0431 (4)
C1	0.36077 (10)	0.5444 (3)	0.12956 (14)	0.0370 (5)
C2	0.35148 (13)	0.6223 (3)	0.22873 (16)	0.0544 (6)
H2	0.3115	0.5788	0.2703	0.065*
C3	0.40176 (17)	0.7653 (4)	0.2661 (2)	0.0726 (8)
H3A	0.3947	0.8188	0.3323	0.087*
C4	0.46131 (16)	0.8286 (4)	0.2071 (3)	0.0770 (8)
H4	0.4951	0.9238	0.2333	0.092*
C5	0.47118 (14)	0.7520 (4)	0.1099 (2)	0.0726 (8)
H5	0.5119	0.7947	0.0694	0.087*
C6	0.42080 (12)	0.6104 (3)	0.07061 (17)	0.0521 (6)
H6	0.4277	0.5596	0.0036	0.062*
C7	0.30659 (10)	0.3854 (3)	0.09099 (13)	0.0359 (5)
C8	0.31075 (11)	0.2087 (3)	0.16286 (16)	0.0449 (5)
H8A	0.3310	0.1000	0.1255	0.054*
H8B	0.3443	0.2320	0.2262	0.054*
C9	0.22789 (11)	0.1762 (3)	0.19037 (13)	0.0339 (4)
C10	0.20331 (12)	0.0106 (3)	0.25333 (15)	0.0469 (5)
H10A	0.1476	0.0176	0.2628	0.070*
H10B	0.2314	0.0116	0.3214	0.070*
H10C	0.2150	−0.1048	0.2166	0.070*
C11	0.18790 (11)	0.5957 (3)	0.05705 (13)	0.0334 (4)
C12	0.10340 (10)	0.6415 (2)	0.07655 (13)	0.0297 (4)
C13	0.07060 (11)	0.6357 (3)	0.17484 (14)	0.0375 (5)
H13	0.0990	0.5858	0.2335	0.045*
C14	−0.00432 (12)	0.7045 (3)	0.18447 (15)	0.0430 (5)
H14	−0.0247	0.7031	0.2515	0.052*
C15	−0.01844 (11)	0.7738 (3)	0.00927 (15)	0.0407 (5)
H15	−0.0493	0.8176	−0.0488	0.049*
C16	0.05681 (11)	0.7135 (3)	−0.00760 (14)	0.0361 (5)
H16	0.0764	0.7210	−0.0750	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0399 (8)	0.0500 (9)	0.0490 (8)	−0.0025 (7)	0.0074 (6)	−0.0062 (7)
O2	0.0370 (8)	0.0445 (9)	0.0556 (8)	0.0018 (7)	0.0082 (6)	0.0166 (7)
O1W	0.0428 (8)	0.0447 (9)	0.0690 (9)	−0.0001 (7)	0.0023 (6)	−0.0063 (7)
N1	0.0297 (9)	0.0353 (9)	0.0368 (8)	−0.0024 (8)	0.0008 (7)	0.0024 (7)
N2	0.0240 (8)	0.0362 (9)	0.0438 (8)	0.0016 (7)	0.0022 (6)	0.0106 (7)
N3	0.0319 (9)	0.0421 (10)	0.0553 (11)	0.0033 (8)	0.0027 (8)	−0.0013 (8)
C1	0.0274 (10)	0.0373 (11)	0.0457 (11)	0.0028 (9)	−0.0031 (8)	0.0043 (9)
C2	0.0458 (13)	0.0606 (16)	0.0564 (13)	0.0085 (12)	−0.0017 (10)	−0.0066 (11)
C3	0.0676 (18)	0.0689 (19)	0.0786 (17)	0.0129 (16)	−0.0232 (14)	−0.0247 (14)
C4	0.0537 (17)	0.0506 (17)	0.123 (2)	−0.0011 (14)	−0.0303 (16)	−0.0094 (16)
C5	0.0484 (15)	0.0663 (19)	0.102 (2)	−0.0183 (14)	−0.0027 (14)	0.0144 (16)
C6	0.0413 (12)	0.0551 (15)	0.0598 (13)	−0.0080 (11)	0.0028 (10)	0.0046 (11)
C7	0.0253 (10)	0.0393 (12)	0.0434 (11)	0.0041 (9)	0.0048 (8)	0.0036 (9)
C8	0.0352 (11)	0.0387 (12)	0.0605 (12)	0.0049 (10)	0.0006 (9)	0.0118 (10)
C9	0.0355 (11)	0.0314 (11)	0.0345 (9)	0.0005 (9)	0.0000 (8)	−0.0005 (8)
C10	0.0472 (12)	0.0370 (12)	0.0567 (12)	0.0009 (11)	0.0055 (9)	0.0069 (10)
C11	0.0294 (10)	0.0355 (11)	0.0349 (10)	0.0017 (9)	−0.0009 (8)	0.0008 (9)
C12	0.0289 (10)	0.0249 (10)	0.0351 (10)	−0.0014 (8)	0.0004 (8)	−0.0009 (8)
C13	0.0348 (11)	0.0420 (12)	0.0355 (10)	0.0022 (10)	−0.0015 (8)	0.0012 (9)
C14	0.0381 (12)	0.0480 (13)	0.0431 (11)	−0.0005 (10)	0.0053 (9)	−0.0035 (9)
C15	0.0343 (11)	0.0386 (12)	0.0480 (12)	0.0020 (10)	−0.0095 (9)	0.0048 (9)
C16	0.0363 (11)	0.0358 (11)	0.0360 (10)	0.0017 (9)	−0.0013 (8)	0.0013 (8)

O1—C7	1.401 (2)	C5—C6	1.386 (3)
O1—H1	0.9166	C5—H5	0.9300
O2—C11	1.229 (2)	C6—H6	0.9300
O1W—H1W1	0.9200	C7—C8	1.536 (3)
O1W—H2W1	0.8517	C8—C9	1.483 (3)
N1—C9	1.279 (2)	C8—H8A	0.9700
N1—N2	1.408 (2)	C8—H8B	0.9700
N2—C11	1.345 (2)	C9—C10	1.481 (3)
N2—C7	1.501 (2)	C10—H10A	0.9600
N3—C15	1.334 (2)	C10—H10B	0.9600
N3—C14	1.336 (2)	C10—H10C	0.9600
C1—C6	1.373 (3)	C11—C12	1.502 (2)
C1—C2	1.382 (3)	C12—C16	1.386 (2)
C1—C7	1.511 (3)	C12—C13	1.386 (2)
C2—C3	1.384 (3)	C13—C14	1.371 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.360 (4)	C14—H14	0.9300
C3—H3A	0.9300	C15—C16	1.372 (3)
C4—C5	1.358 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C7—O1—H1	104.0	C9—C8—H8A	110.9
H1W1—O1W—H2W1	104.4	C7—C8—H8A	110.9
C9—N1—N2	107.33 (14)	C9—C8—H8B	110.9
C11—N2—N1	122.54 (15)	C7—C8—H8B	110.9
C11—N2—C7	124.25 (15)	H8A—C8—H8B	108.9
N1—N2—C7	113.06 (13)	N1—C9—C10	122.21 (17)
C15—N3—C14	115.90 (17)	N1—C9—C8	114.87 (16)
C6—C1—C2	118.6 (2)	C10—C9—C8	122.91 (17)
C6—C1—C7	122.12 (17)	C9—C10—H10A	109.5
C2—C1—C7	119.22 (17)	C9—C10—H10B	109.5
C1—C2—C3	119.9 (2)	H10A—C10—H10B	109.5
C1—C2—H2	120.1	C9—C10—H10C	109.5
C3—C2—H2	120.1	H10A—C10—H10C	109.5
C4—C3—C2	120.9 (2)	H10B—C10—H10C	109.5
C4—C3—H3A	119.5	O2—C11—N2	121.24 (17)
C2—C3—H3A	119.5	O2—C11—C12	118.90 (16)
C5—C4—C3	119.6 (2)	N2—C11—C12	119.85 (16)
C5—C4—H4	120.2	C16—C12—C13	117.15 (17)
C3—C4—H4	120.2	C16—C12—C11	117.65 (15)
C4—C5—C6	120.3 (2)	C13—C12—C11	124.86 (16)
C4—C5—H5	119.9	C14—C13—C12	119.10 (17)
C6—C5—H5	119.9	C14—C13—H13	120.4
C1—C6—C5	120.7 (2)	C12—C13—H13	120.4
C1—C6—H6	119.7	N3—C14—C13	124.36 (18)
C5—C6—H6	119.7	N3—C14—H14	117.8
O1—C7—N2	110.42 (13)	C13—C14—H14	117.8
O1—C7—C1	109.67 (14)	N3—C15—C16	123.97 (17)
N2—C7—C1	110.60 (15)	N3—C15—H15	118.0
O1—C7—C8	112.56 (16)	C16—C15—H15	118.0
N2—C7—C8	99.74 (14)	C15—C16—C12	119.47 (17)
C1—C7—C8	113.51 (15)	C15—C16—H16	120.3
C9—C8—C7	104.34 (15)	C12—C16—H16	120.3
C9—N1—N2—C11	−179.02 (16)	N2—C7—C8—C9	7.23 (18)
C9—N1—N2—C7	5.31 (18)	C1—C7—C8—C9	124.87 (16)
C6—C1—C2—C3	0.6 (3)	N2—N1—C9—C10	179.31 (16)
C7—C1—C2—C3	178.63 (19)	N2—N1—C9—C8	0.2 (2)
C1—C2—C3—C4	−1.1 (4)	C7—C8—C9—N1	−5.2 (2)
C2—C3—C4—C5	0.7 (4)	C7—C8—C9—C10	175.69 (17)
C3—C4—C5—C6	0.2 (4)	N1—N2—C11—O2	−173.53 (15)
C2—C1—C6—C5	0.2 (3)	C7—N2—C11—O2	1.7 (3)
C7—C1—C6—C5	−177.7 (2)	N1—N2—C11—C12	7.4 (2)
C4—C5—C6—C1	−0.6 (4)	C7—N2—C11—C12	−177.38 (15)
C11—N2—C7—O1	−64.9 (2)	O2—C11—C12—C16	39.6 (2)
N1—N2—C7—O1	110.71 (15)	N2—C11—C12—C16	−141.39 (18)
C11—N2—C7—C1	56.7 (2)	O2—C11—C12—C13	−133.48 (19)
N1—N2—C7—C1	−127.72 (15)	N2—C11—C12—C13	45.6 (3)
C11—N2—C7—C8	176.49 (17)	C16—C12—C13—C14	−1.5 (3)
N1—N2—C7—C8	−7.92 (18)	C11—C12—C13—C14	171.52 (18)
C6—C1—C7—O1	−8.6 (2)	C15—N3—C14—C13	−0.4 (3)
C2—C1—C7—O1	173.52 (17)	C12—C13—C14—N3	2.0 (3)
C6—C1—C7—N2	−130.57 (19)	C14—N3—C15—C16	−1.7 (3)
C2—C1—C7—N2	51.5 (2)	N3—C15—C16—C12	2.1 (3)
C6—C1—C7—C8	118.3 (2)	C13—C12—C16—C15	−0.4 (3)
C2—C1—C7—C8	−59.6 (2)	C11—C12—C16—C15	−173.97 (17)
O1—C7—C8—C9	−109.82 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wi	0.92	1.84	2.7490 (19)	173.
O1W—H1W1···O2ii	0.92	1.89	2.8003 (19)	169.
O1W—H2W1···N3iii	0.85	2.13	2.976 (2)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1Wi	0.92	1.84	2.7490 (19)	173
O1W—H1W1⋯O2ii	0.92	1.89	2.8003 (19)	169
O1W—H2W1⋯N3iii	0.85	2.13	2.976 (2)	173

Symmetry codes: (i) ; (ii) ; (iii) .