5-Cyclo-hexyl-4-methyl-1H-pyrazol-3(2H)-one monohydrate.

In the title compound, C(10)H(16)N(2)O·H(2)O, the cyclo-hexane ring is in a chair conformation and its least-squares plane makes a dihedral angle of 53.68 (5)° with the approximately planar pyrazole ring [maximum deviation = 0.034 (1) Å]. Pairs of inter-molecular N-H⋯O hydrogen bonds form inversion dimers between neighbouring pyrazolone mol-ecules, generating R(2) (2)(8) ring motifs. The pyrazolone and water mol-ecules are further linked by inter-molecular N-H⋯O, C-H⋯O and O-H⋯O hydrogen bonds into two-dimensional sheets parallel to the bc plane.

Related literature

For pyrazole derivatives and their microbial activities, see: Ragavan et al. (2009 ▶, 2010 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶,c ▶). For ring conformations, see: Cremer & Pople (1975 ▶). 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

C10H16N2O·H2O

M = 198.26

Monoclinic,

a = 13.4959 (3) Å

b = 6.2497 (1) Å

c = 13.9268 (3) Å

β = 112.782 (1)°

V = 1083.02 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.46 × 0.27 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.981

26403 measured reflections

4715 independent reflections

3863 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.03

4715 reflections

199 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810039164/is2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039164/is2608Isup2.hkl

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

C10H16N2O·H2O	F(000) = 432
Mr = 198.26	Dx = 1.216 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9296 reflections
a = 13.4959 (3) Å	θ = 3.0–34.7°
b = 6.2497 (1) Å	µ = 0.09 mm−1
c = 13.9268 (3) Å	T = 100 K
β = 112.782 (1)°	Block, colourless
V = 1083.02 (4) Å3	0.46 × 0.27 × 0.23 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4715 independent reflections
Radiation source: fine-focus sealed tube	3863 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 35.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→21
Tmin = 0.962, Tmax = 0.981	k = −10→10
26403 measured reflections	l = −21→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.2027P] where P = (Fo2 + 2Fc2)/3
4715 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.28 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	0.47692 (5)	0.58283 (9)	0.36443 (4)	0.01649 (11)
N1	0.35298 (5)	0.86770 (11)	0.49923 (5)	0.01570 (12)
N2	0.43455 (5)	0.74179 (11)	0.49437 (5)	0.01560 (12)
C1	0.22589 (7)	1.31323 (13)	0.36124 (7)	0.02077 (15)
C2	0.12483 (7)	1.45257 (14)	0.33028 (7)	0.02375 (16)
C3	0.07738 (7)	1.44773 (14)	0.41354 (7)	0.02298 (16)
C4	0.05310 (7)	1.21880 (14)	0.43594 (7)	0.02146 (16)
C5	0.15219 (7)	1.07543 (13)	0.46434 (7)	0.01902 (14)
C6	0.19853 (6)	1.08190 (12)	0.37959 (6)	0.01492 (13)
C7	0.29215 (6)	0.93410 (11)	0.40136 (5)	0.01425 (13)
C8	0.41832 (6)	0.71084 (12)	0.39255 (5)	0.01420 (13)
C9	0.32907 (6)	0.83939 (12)	0.33169 (5)	0.01507 (13)
C10	0.28323 (7)	0.85575 (15)	0.21552 (6)	0.02220 (16)
O1W	0.39076 (5)	0.38748 (10)	0.17409 (5)	0.02017 (12)
H1A	0.2820 (10)	1.3696 (19)	0.4284 (10)	0.026 (3)*
H1B	0.2551 (10)	1.319 (2)	0.3063 (11)	0.030 (3)*
H2A	0.0700 (11)	1.398 (2)	0.2637 (11)	0.029 (3)*
H2B	0.1410 (11)	1.602 (2)	0.3181 (11)	0.033 (3)*
H3A	0.1301 (11)	1.516 (2)	0.4797 (10)	0.028 (3)*
H3B	0.0083 (10)	1.536 (2)	0.3909 (10)	0.027 (3)*
H4A	−0.0056 (10)	1.161 (2)	0.3741 (11)	0.029 (3)*
H4B	0.0270 (10)	1.214 (2)	0.4932 (10)	0.028 (3)*
H5A	0.2079 (11)	1.124 (2)	0.5307 (11)	0.032 (3)*
H5B	0.1334 (10)	0.922 (2)	0.4749 (10)	0.025 (3)*
H6	0.1416 (10)	1.028 (2)	0.3127 (9)	0.020 (3)*
H10A	0.2285 (15)	0.956 (3)	0.1918 (15)	0.066 (5)*
H10B	0.3351 (14)	0.891 (3)	0.1877 (13)	0.053 (5)*
H10C	0.2553 (13)	0.719 (3)	0.1795 (14)	0.060 (5)*
H1N1	0.3647 (11)	0.938 (2)	0.5581 (11)	0.033 (3)*
H1N2	0.4682 (11)	0.646 (2)	0.5476 (11)	0.034 (3)*
H1W1	0.4222 (13)	0.442 (3)	0.2377 (13)	0.046 (4)*
H1W2	0.4323 (13)	0.284 (3)	0.1729 (13)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0200 (3)	0.0165 (2)	0.0143 (2)	0.00467 (19)	0.00818 (19)	0.00135 (18)
N1	0.0190 (3)	0.0166 (3)	0.0112 (2)	0.0047 (2)	0.0057 (2)	0.0004 (2)
N2	0.0187 (3)	0.0162 (3)	0.0116 (3)	0.0051 (2)	0.0056 (2)	0.0017 (2)
C1	0.0210 (3)	0.0161 (3)	0.0261 (4)	0.0025 (3)	0.0102 (3)	0.0048 (3)
C2	0.0251 (4)	0.0165 (3)	0.0282 (4)	0.0053 (3)	0.0088 (3)	0.0047 (3)
C3	0.0227 (4)	0.0170 (3)	0.0272 (4)	0.0040 (3)	0.0074 (3)	−0.0051 (3)
C4	0.0197 (3)	0.0206 (4)	0.0257 (4)	0.0018 (3)	0.0105 (3)	−0.0039 (3)
C5	0.0208 (3)	0.0179 (3)	0.0211 (3)	0.0028 (3)	0.0113 (3)	0.0010 (3)
C6	0.0158 (3)	0.0139 (3)	0.0145 (3)	0.0018 (2)	0.0053 (2)	−0.0002 (2)
C7	0.0166 (3)	0.0135 (3)	0.0122 (3)	0.0015 (2)	0.0052 (2)	0.0010 (2)
C8	0.0173 (3)	0.0138 (3)	0.0118 (3)	0.0012 (2)	0.0060 (2)	0.0009 (2)
C9	0.0180 (3)	0.0156 (3)	0.0112 (3)	0.0034 (2)	0.0052 (2)	0.0015 (2)
C10	0.0275 (4)	0.0259 (4)	0.0118 (3)	0.0087 (3)	0.0059 (3)	0.0024 (3)
O1W	0.0246 (3)	0.0216 (3)	0.0139 (2)	0.0035 (2)	0.0071 (2)	0.0007 (2)

O1—C8	1.2880 (9)	C4—C5	1.5290 (11)
N1—C7	1.3555 (9)	C4—H4A	0.985 (14)
N1—N2	1.3760 (9)	C4—H4B	0.989 (13)
N1—H1N1	0.889 (14)	C5—C6	1.5354 (10)
N2—C8	1.3622 (9)	C5—H5A	0.986 (14)
N2—H1N2	0.923 (14)	C5—H5B	1.020 (13)
C1—C2	1.5326 (12)	C6—C7	1.4982 (10)
C1—C6	1.5378 (11)	C6—H6	1.009 (12)
C1—H1A	1.012 (13)	C7—C9	1.3836 (10)
C1—H1B	0.987 (13)	C8—C9	1.4226 (10)
C2—C3	1.5267 (13)	C9—C10	1.4953 (11)
C2—H2A	0.995 (14)	C10—H10A	0.93 (2)
C2—H2B	0.986 (14)	C10—H10B	0.948 (17)
C3—C4	1.5267 (13)	C10—H10C	0.987 (19)
C3—H3A	1.013 (14)	O1W—H1W1	0.888 (17)
C3—H3B	1.022 (13)	O1W—H1W2	0.858 (18)
C7—N1—N2	108.07 (6)	H4A—C4—H4B	106.1 (11)
C7—N1—H1N1	126.7 (9)	C4—C5—C6	111.20 (7)
N2—N1—H1N1	118.0 (9)	C4—C5—H5A	109.6 (8)
C8—N2—N1	108.86 (6)	C6—C5—H5A	108.8 (8)
C8—N2—H1N2	125.1 (9)	C4—C5—H5B	110.4 (7)
N1—N2—H1N2	119.0 (8)	C6—C5—H5B	109.5 (7)
C2—C1—C6	109.64 (7)	H5A—C5—H5B	107.3 (11)
C2—C1—H1A	109.2 (7)	C7—C6—C5	113.01 (6)
C6—C1—H1A	108.4 (7)	C7—C6—C1	112.05 (6)
C2—C1—H1B	110.0 (8)	C5—C6—C1	110.36 (6)
C6—C1—H1B	110.7 (8)	C7—C6—H6	105.2 (7)
H1A—C1—H1B	108.9 (10)	C5—C6—H6	108.0 (7)
C3—C2—C1	111.37 (7)	C1—C6—H6	107.9 (7)
C3—C2—H2A	108.8 (8)	N1—C7—C9	109.38 (6)
C1—C2—H2A	109.1 (8)	N1—C7—C6	121.81 (6)
C3—C2—H2B	109.6 (8)	C9—C7—C6	128.78 (7)
C1—C2—H2B	110.7 (8)	O1—C8—N2	122.31 (7)
H2A—C2—H2B	107.2 (11)	O1—C8—C9	130.36 (6)
C2—C3—C4	111.10 (7)	N2—C8—C9	107.32 (6)
C2—C3—H3A	109.2 (7)	C7—C9—C8	105.99 (6)
C4—C3—H3A	109.7 (8)	C7—C9—C10	128.25 (7)
C2—C3—H3B	110.8 (7)	C8—C9—C10	125.68 (7)
C4—C3—H3B	109.0 (8)	C9—C10—H10A	111.8 (12)
H3A—C3—H3B	106.9 (11)	C9—C10—H10B	113.4 (10)
C3—C4—C5	111.51 (7)	H10A—C10—H10B	108.0 (15)
C3—C4—H4A	109.1 (8)	C9—C10—H10C	114.0 (11)
C5—C4—H4A	109.8 (8)	H10A—C10—H10C	108.0 (15)
C3—C4—H4B	111.4 (8)	H10B—C10—H10C	101.0 (14)
C5—C4—H4B	108.8 (8)	H1W1—O1W—H1W2	104.0 (14)
C7—N1—N2—C8	−6.34 (8)	C5—C6—C7—C9	154.47 (8)
C6—C1—C2—C3	57.93 (10)	C1—C6—C7—C9	−80.10 (10)
C1—C2—C3—C4	−56.21 (10)	N1—N2—C8—O1	−173.49 (7)
C2—C3—C4—C5	54.34 (10)	N1—N2—C8—C9	5.81 (8)
C3—C4—C5—C6	−54.98 (9)	N1—C7—C9—C8	−0.75 (9)
C4—C5—C6—C7	−176.77 (7)	C6—C7—C9—C8	−178.70 (7)
C4—C5—C6—C1	56.89 (9)	N1—C7—C9—C10	176.30 (8)
C2—C1—C6—C7	175.19 (7)	C6—C7—C9—C10	−1.65 (14)
C2—C1—C6—C5	−57.94 (9)	O1—C8—C9—C7	176.10 (8)
N2—N1—C7—C9	4.32 (9)	N2—C8—C9—C7	−3.12 (8)
N2—N1—C7—C6	−177.56 (6)	O1—C8—C9—C10	−1.05 (14)
C5—C6—C7—N1	−23.26 (10)	N2—C8—C9—C10	179.74 (8)
C1—C6—C7—N1	102.18 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1Wi	0.889 (14)	1.866 (14)	2.7513 (9)	173.7 (12)
N2—H1N2···O1ii	0.924 (14)	1.842 (13)	2.7552 (9)	169.5 (13)
O1W—H1W1···O1	0.889 (17)	1.851 (17)	2.7354 (8)	173.2 (18)
O1W—H1W2···O1iii	0.860 (19)	1.961 (19)	2.8007 (9)	165.0 (16)
C5—H5A···O1Wi	0.987 (14)	2.503 (15)	3.4161 (12)	153.7 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1Wi	0.889 (14)	1.866 (14)	2.7513 (9)	173.7 (12)
N2—H1N2⋯O1ii	0.924 (14)	1.842 (13)	2.7552 (9)	169.5 (13)
O1W—H1W1⋯O1	0.889 (17)	1.851 (17)	2.7354 (8)	173.2 (18)
O1W—H1W2⋯O1iii	0.860 (19)	1.961 (19)	2.8007 (9)	165.0 (16)
C5—H5A⋯O1Wi	0.987 (14)	2.503 (15)	3.4161 (12)	153.7 (11)

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