3-(5-Methyl-3-phenyl-1H-pyrazol-1-yl)propanamide monohydrate.

In the title compound, C(13)H(15)N(3)O·H(2)O, the dihedral angle between the pyrazole and benzene rings is 26.6 (2)° and the N-C-C-C torsion angle is 153.6 (3)°. In the crystal, adjacent mol-ecules are linked by N-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds into a network structure running along the a axis.

Related literature

For the potential applications of substituted pyrazole derivatives as ligands, see: Shaw et al. (2004 ▶;) n class="Gene">Pal et al. (2005 ▶). For the design and synthesis of various pyrazole ligands with special structural properties to fulfill the stereochemical requirements of the metal-binding sites, see: Bell et al. (2003 ▶); Paul et al. (2004 ▶) For pyrazole ligands with propanamide side-chains, see: Huang et al. (2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C13H15N3O·n class="Chemical">H2O

M = 247.30

Orthorhombic,

a = 6.5482 (13) Å

b = 12.609 (3) Å

c = 16.606 (3) Å

V = 1371.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.45 × 0.23 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.977, T max = 0.990

13414 measured reflections

1815 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.140

S = 1.08

1815 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.16 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998) ▶; cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005035X/im2245sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005035X/im2245Isup2.hkl

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

C13H15N3O·H2O	F(000) = 528
Mr = 247.30	Dx = 1.198 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 13460 reflections
a = 6.5482 (13) Å	θ = 3.2–27.4°
b = 12.609 (3) Å	µ = 0.08 mm−1
c = 16.606 (3) Å	T = 296 K
V = 1371.1 (5) Å3	Chip, colorless
Z = 4	0.45 × 0.23 × 0.12 mm

Rigaku R-AXIS RAPID diffractometer	1815 independent reflections
Radiation source: fine-focus sealed tube	1323 reflections with I > 2σ(I)
graphite	Rint = 0.056
ω scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→7
Tmin = 0.977, Tmax = 0.990	k = −16→16
13414 measured reflections	l = −21→21

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.2276P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1815 reflections	Δρmax = 0.23 e Å−3
164 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (6)

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	0.1503 (3)	0.37278 (16)	0.44426 (14)	0.0598 (6)
N3	0.6165 (4)	0.63188 (17)	0.33836 (14)	0.0455 (6)
N2	0.4723 (4)	0.58241 (16)	0.29243 (14)	0.0456 (6)
C7	0.7043 (4)	0.7022 (2)	0.28840 (17)	0.0432 (6)
C1	0.0612 (4)	0.4538 (2)	0.42065 (18)	0.0451 (7)
C3	0.3511 (4)	0.4985 (2)	0.32841 (19)	0.0505 (7)
H3A	0.4382	0.4554	0.3625	0.061*
H3B	0.2976	0.4534	0.2861	0.061*
N1	−0.1361 (4)	0.4692 (2)	0.43135 (16)	0.0572 (7)
H1A	−0.2084	0.4220	0.4556	0.069*
H1B	−0.1926	0.5264	0.4141	0.069*
C6	0.6151 (5)	0.6976 (2)	0.21225 (18)	0.0529 (7)
H6A	0.6495	0.7386	0.1677	0.063*
C8	0.8697 (5)	0.7707 (2)	0.31861 (18)	0.0463 (7)
C2	0.1763 (5)	0.5407 (2)	0.3778 (2)	0.0578 (8)
H2A	0.0830	0.5788	0.3428	0.069*
H2B	0.2287	0.5905	0.4172	0.069*
C4	0.4663 (5)	0.6208 (2)	0.21594 (18)	0.0509 (7)
O2	−0.4388 (4)	0.32706 (19)	0.4938 (2)	0.0888 (10)
H2D	−0.4329	0.2662	0.5146	0.168*
H2C	−0.5655	0.3375	0.4857	0.092*
C9	0.8839 (5)	0.7964 (3)	0.4002 (2)	0.0596 (8)
H9A	0.7863	0.7708	0.4360	0.072*
C12	1.1724 (6)	0.8742 (3)	0.2958 (3)	0.0849 (12)
H12A	1.2706	0.9003	0.2605	0.102*
C13	1.0158 (5)	0.8108 (2)	0.2666 (2)	0.0612 (9)
H13A	1.0090	0.7952	0.2119	0.073*
C10	1.0405 (6)	0.8592 (3)	0.4285 (2)	0.0767 (11)
H10A	1.0489	0.8748	0.4832	0.092*
C5	0.3188 (6)	0.5832 (3)	0.1551 (2)	0.0749 (11)
H5A	0.2362	0.5278	0.1778	0.112*
H5B	0.3913	0.5563	0.1092	0.112*
H5C	0.2328	0.6410	0.1387	0.112*
C11	1.1840 (7)	0.8988 (4)	0.3764 (3)	0.0923 (14)
H11A	1.2884	0.9421	0.3955	0.111*

	U11	U22	U33	U12	U13	U23
O1	0.0465 (11)	0.0555 (11)	0.0775 (15)	0.0054 (11)	0.0067 (12)	0.0248 (11)
N3	0.0438 (12)	0.0434 (12)	0.0493 (13)	−0.0047 (11)	0.0011 (11)	0.0076 (10)
N2	0.0465 (13)	0.0423 (11)	0.0479 (13)	−0.0057 (11)	0.0041 (12)	0.0079 (10)
C7	0.0445 (14)	0.0357 (12)	0.0495 (15)	−0.0022 (12)	0.0054 (14)	0.0087 (12)
C1	0.0418 (15)	0.0457 (14)	0.0480 (16)	0.0001 (13)	0.0033 (13)	0.0050 (13)
C3	0.0473 (15)	0.0414 (13)	0.0628 (18)	−0.0064 (14)	0.0083 (15)	0.0044 (13)
N1	0.0415 (13)	0.0558 (14)	0.0742 (18)	0.0034 (12)	0.0085 (14)	0.0194 (13)
C6	0.0634 (18)	0.0479 (14)	0.0475 (16)	−0.0078 (15)	0.0016 (16)	0.0092 (13)
C8	0.0443 (14)	0.0376 (12)	0.0569 (17)	−0.0012 (12)	0.0000 (15)	0.0088 (12)
C2	0.0488 (17)	0.0455 (14)	0.079 (2)	0.0016 (15)	0.0151 (17)	0.0110 (15)
C4	0.0569 (17)	0.0487 (14)	0.0470 (15)	−0.0042 (15)	0.0000 (15)	0.0032 (13)
O2	0.0472 (13)	0.0764 (16)	0.143 (3)	−0.0005 (12)	0.0038 (16)	0.0493 (17)
C9	0.0590 (19)	0.0586 (17)	0.0611 (19)	−0.0053 (17)	0.0007 (17)	0.0017 (15)
C12	0.060 (2)	0.102 (3)	0.092 (3)	−0.030 (2)	0.008 (2)	0.011 (2)
C13	0.0547 (18)	0.0627 (18)	0.066 (2)	−0.0080 (17)	0.0053 (17)	0.0067 (16)
C10	0.073 (2)	0.084 (2)	0.074 (2)	−0.014 (2)	−0.014 (2)	−0.007 (2)
C5	0.086 (3)	0.078 (2)	0.060 (2)	−0.019 (2)	−0.014 (2)	0.0029 (18)
C11	0.069 (3)	0.109 (3)	0.098 (3)	−0.033 (3)	−0.011 (2)	−0.003 (3)

O1—C1	1.240 (3)	C2—H2A	0.9700
N3—C7	1.344 (3)	C2—H2B	0.9700
N3—N2	1.365 (3)	C4—C5	1.476 (4)
N2—C4	1.360 (4)	O2—H2D	0.8424
N2—C3	1.451 (3)	O2—H2C	0.8505
C7—C6	1.394 (4)	C9—C10	1.378 (5)
C7—C8	1.473 (4)	C9—H9A	0.9300
C1—N1	1.319 (4)	C12—C11	1.376 (6)
C1—C2	1.509 (4)	C12—C13	1.388 (5)
C3—C2	1.505 (4)	C12—H12A	0.9300
C3—H3A	0.9700	C13—H13A	0.9300
C3—H3B	0.9700	C10—C11	1.371 (6)
N1—H1A	0.8600	C10—H10A	0.9300
N1—H1B	0.8600	C5—H5A	0.9600
C6—C4	1.375 (4)	C5—H5B	0.9600
C6—H6A	0.9300	C5—H5C	0.9600
C8—C13	1.385 (4)	C11—H11A	0.9300
C8—C9	1.397 (4)
C7—N3—N2	104.6 (2)	C3—C2—H2B	109.1
C4—N2—N3	112.3 (2)	C1—C2—H2B	109.1
C4—N2—C3	128.9 (3)	H2A—C2—H2B	107.9
N3—N2—C3	118.8 (2)	N2—C4—C6	105.8 (3)
N3—C7—C6	110.7 (2)	N2—C4—C5	122.9 (3)
N3—C7—C8	119.4 (2)	C6—C4—C5	131.3 (3)
C6—C7—C8	129.9 (2)	H2D—O2—H2C	104.5
O1—C1—N1	122.7 (3)	C10—C9—C8	120.9 (3)
O1—C1—C2	120.8 (3)	C10—C9—H9A	119.6
N1—C1—C2	116.5 (3)	C8—C9—H9A	119.6
N2—C3—C2	112.5 (2)	C11—C12—C13	120.7 (4)
N2—C3—H3A	109.1	C11—C12—H12A	119.6
C2—C3—H3A	109.1	C13—C12—H12A	119.6
N2—C3—H3B	109.1	C8—C13—C12	120.1 (3)
C2—C3—H3B	109.1	C8—C13—H13A	119.9
H3A—C3—H3B	107.8	C12—C13—H13A	119.9
C1—N1—H1A	120.0	C11—C10—C9	120.3 (4)
C1—N1—H1B	120.0	C11—C10—H10A	119.9
H1A—N1—H1B	120.0	C9—C10—H10A	119.9
C4—C6—C7	106.6 (3)	C4—C5—H5A	109.5
C4—C6—H6A	126.7	C4—C5—H5B	109.5
C7—C6—H6A	126.7	H5A—C5—H5B	109.5
C13—C8—C9	118.4 (3)	C4—C5—H5C	109.5
C13—C8—C7	120.6 (3)	H5A—C5—H5C	109.5
C9—C8—C7	121.0 (3)	H5B—C5—H5C	109.5
C3—C2—C1	112.4 (2)	C10—C11—C12	119.6 (4)
C3—C2—H2A	109.1	C10—C11—H11A	120.2
C1—C2—H2A	109.1	C12—C11—H11A	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.03	2.867 (3)	165.
N1—H1B···N3i	0.86	2.22	3.036 (3)	159.
O2—H2D···O1ii	0.84	1.96	2.783 (3)	166.2
O2—H2C···O1i	0.85	2.03	2.872 (3)	168.5

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.03	2.867 (3)	165
N1—H1B⋯N3i	0.86	2.22	3.036 (3)	159
O2—H2D⋯O1ii	0.84	1.96	2.783 (3)	166.2
O2—H2C⋯O1i	0.85	2.03	2.872 (3)	168.5

Symmetry codes: (i) ; (ii) .