1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4-dihydro­pyridin-3-yl]ethanone monohydrate

Islor, A.M.; Malladi, S.; Sundershan, S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812042614

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3156-o3157

doi:10.1107/S1600536812042614

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1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4-dihydropyridin-3-yl]ethanone monohydrate

Arun M. Islor,^a Shridhar Malladi,^a S. Sundershan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India, ^bUAS Hebbal, Veterinary College, Department of Microbiology, Bangalore 24, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 10 October 2012; accepted 11 October 2012; online 20 October 2012)

In the title compound, C₂₀H₂₁N₃O₂·H₂O, the aza-substitued six-membered ring adopts a ^L4B conformation. In the crystal, classical N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds connect the entities into a three-dimensional network. Intramolecular C—H⋯O contacts are also observed.

Related literature

For the pharmaceutical properties of 1,4-dihydropyridine-derived drugs, see: Janis & Triggle (1983 ); Boecker & Guengerich (1986 ); Gordeev et al. (1996 ); Buhler & Kiowski (1987 ); Vo et al. (1995 ). For the conformational analysis of puckering factors of five- and six-membered rings, see: Cremer & Pople (1975 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁N₃O₂·H₂O
M_r = 353.41
Monoclinic, P 2₁ /c
a = 10.3516 (2) Å
b = 12.4352 (3) Å
c = 15.4101 (3) Å
β = 112.798 (1)°
V = 1828.68 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 K
0.41 × 0.34 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.965, T_max = 0.984
17882 measured reflections
4559 independent reflections
3849 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.114
S = 1.04
4559 reflections
255 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.938 (19)	1.855 (19)	2.7822 (14)	169.1 (16)
N3—H3⋯N1ⁱⁱ	0.878 (17)	2.075 (17)	2.9454 (13)	171.1 (15)
O3—H3B⋯O2ⁱⁱⁱ	0.86 (2)	1.92 (2)	2.7838 (13)	175.8 (17)
O3—H3C⋯O1^iv	0.87 (2)	1.88 (2)	2.7372 (14)	169.8 (18)
C6—H6⋯O2	0.95	2.44	3.282 (2)	148
C10—H10⋯O2	1.00	2.33	2.7624 (13)	105
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812042614/hg5260sup1.cif

Supporting information file. DOI: 10.1107/S1600536812042614/hg5260Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042614/hg5260Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812042614/hg5260Isup4.cml

checkCIF report

Comment top

In recent years, considerable attention has been paid to the synthesis of 1,4-dihydropyridines owing to their significant biological activity. 1,4-Dihydropyridine-containing drugs (1,4-DHPs), such as nifedipine, nicardipine, amlodipine, felodipine and others have been found to be useful as calcium channel blockers (Janis & Triggle 1983; Boecker & Guengerich 1986; Gordeev et al., 1996) and are used most frequently as cardiovascular agents for the treatment of hypertension (Buhler & Kiowski 1987). A number of DHP derivatives are employed as potential drug candidates for the treatment of congestive heart failure (Vo et al., 1995). Prompted by the diverse activities of 1,4-Dihydropyridines, we have synthesized the title compound to study its crystal structure.

The molecule features a pyrazole core bearing a phenyl as well as a 1,4-dihydropyridine-derived substituent. The six-membered ring of the latter adopts a ^L4B conformation according to a puckering analysis (Cremer & Pople, 1975). The least-squares planes defined by the respective intracyclic atoms of the phenyl group as well as the 1,4-dihydropyridine core enclose angles of 52.79 (8) ° and 88.10 (7) ° with the least-squares plane defined by the non-hydrogen atoms of the central pyrazole core (Fig. 1).

In the crystal, classical hydrogen bonds of the O–H···O, N–H···O and N–H···N type are apparent involving both ketonic oxygen atoms and the non-protonated nitrogen atom as acceptors. In addition, two intramolecular C–H···O contacts can be observed whose range falls by more than 0.2 Å below the sum of van-der-Waals radii of the atoms participating. The latter stem from a hydrogen atom on the phenyl group as well as the methine group and have the same ketonic oxygen atom as acceptor. In total, the entities of the title compound are connected to a three-dimensional network in the crystal structure. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is S(5)S(9)DDDC¹₁(8) on the unary level. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 4.7199 (10) Å and is apparent between the pyrazol and the phenyl moiety in neighbouring molecules (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For the pharmaceutical properties of 1,4-dihydropyridine-derived drugs, see: Janis & Triggle (1983); Boecker & Guengerich (1986); Gordeev et al. (1996); Buhler & Kiowski (1987); Vo et al. (1995). For the conformational analysis of puckering factors of five- and six-membered rings, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

3-phenyl-1H-pyrazole-4-carbaldehyde (0.172 g, 1.0 mmol), acetylacetone (0.2 g, 2.0 mmol) and ammonium acetate (0.092 g, 1.2 mmol) were suspended in ethanol (7 ml) and were refluxed for 5 h. After completion of the reaction, the reaction mixture was concentrated and poured into crushed ice. The precipitated product was filtered and washed with water. The resulting solid was recrystallized from a mixture of ethanol and water (v/v = 1:1), yield: 0.255 g (76.1%)

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 0 - 1]. For clarity, only a selection of contacts apparent in the crystal structure is depicted. Symmetry operators: ⁱ -x, y + 1/2, -z + 1/2; ⁱⁱ x, -y + 1/2, z + 1/2; ⁱⁱⁱ x - 1, -y + 1/2, z + 1/2; ^iv -x, y - 1/2, -z + 1/2.
	Fig. 3. Molecular packing of the title compound, viewed along [0 1 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4- dihydropyridin-3-yl]ethanone monohydrate top

Crystal data top

C₂₀H₂₁N₃O₂·H₂O	F(000) = 752
M_r = 353.41	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 428–430 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.3516 (2) Å	Cell parameters from 8726 reflections
b = 12.4352 (3) Å	θ = 2.7–28.3°
c = 15.4101 (3) Å	µ = 0.09 mm⁻¹
β = 112.798 (1)°	T = 200 K
V = 1828.68 (7) Å³	Block, yellow
Z = 4	0.41 × 0.34 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	4559 independent reflections
Radiation source: fine-focus sealed tube	3849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
T_min = 0.965, T_max = 0.984	k = −14→16
17882 measured reflections	l = −20→20

Refinement top

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0577P)² + 0.5735P] where P = (F_o² + 2F_c²)/3
4559 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₁N₃O₂·H₂O	V = 1828.68 (7) Å³
M_r = 353.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3516 (2) Å	µ = 0.09 mm⁻¹
b = 12.4352 (3) Å	T = 200 K
c = 15.4101 (3) Å	0.41 × 0.34 × 0.18 mm
β = 112.798 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4559 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3849 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.984	R_int = 0.015
17882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
4559 reflections	Δρ_min = −0.21 e Å⁻³
255 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.05984 (10)	0.17652 (9)	0.56849 (7)	0.0425 (2)
O2	0.51356 (9)	0.21848 (9)	0.56375 (7)	0.0427 (2)
O3	0.79358 (10)	0.22697 (7)	0.16165 (6)	0.0315 (2)
N1	0.08635 (11)	0.45919 (8)	0.30709 (7)	0.0313 (2)
N2	0.16757 (11)	0.51591 (8)	0.38313 (7)	0.0282 (2)
N3	0.08322 (10)	0.08888 (8)	0.35769 (6)	0.0246 (2)
C1	0.31972 (13)	0.50359 (9)	0.54994 (8)	0.0277 (2)
C2	0.26550 (17)	0.58840 (11)	0.58442 (9)	0.0411 (3)
H2	0.1723	0.6121	0.5501	0.049*
C3	0.3462 (2)	0.63860 (12)	0.66841 (10)	0.0515 (4)
H3A	0.3079	0.6960	0.6915	0.062*
C4	0.4812 (2)	0.60560 (14)	0.71812 (10)	0.0546 (4)
H4	0.5368	0.6403	0.7754	0.066*
C5	0.53562 (17)	0.52211 (18)	0.68471 (11)	0.0608 (5)
H5	0.6292	0.4994	0.7192	0.073*
C6	0.45549 (14)	0.47036 (14)	0.60104 (10)	0.0439 (3)
H6	0.4941	0.4122	0.5791	0.053*
C7	0.23241 (11)	0.45289 (9)	0.45943 (8)	0.0240 (2)
C8	0.19044 (11)	0.34797 (9)	0.43179 (7)	0.0216 (2)
C9	0.09862 (13)	0.35805 (9)	0.33685 (8)	0.0285 (2)
H9	0.0509	0.2992	0.2985	0.034*
C10	0.22607 (10)	0.24440 (8)	0.48768 (7)	0.0204 (2)
H10	0.2897	0.2617	0.5539	0.025*
C11	0.30207 (11)	0.16707 (9)	0.44653 (7)	0.0219 (2)
C12	0.22486 (11)	0.09714 (9)	0.37820 (7)	0.0233 (2)
C13	0.02198 (11)	0.12349 (9)	0.41735 (7)	0.0232 (2)
C14	0.09434 (11)	0.19160 (9)	0.48922 (7)	0.0221 (2)
C15	0.04407 (12)	0.21902 (9)	0.56260 (8)	0.0262 (2)
C16	0.12422 (15)	0.30098 (12)	0.63511 (9)	0.0382 (3)
H16A	0.1371	0.3661	0.6035	0.057*
H16B	0.2160	0.2715	0.6749	0.057*
H16C	0.0718	0.3188	0.6742	0.057*
C17	0.45534 (12)	0.17368 (9)	0.48711 (8)	0.0275 (2)
C18	0.54636 (14)	0.12884 (13)	0.43963 (10)	0.0403 (3)
H18A	0.5101	0.1522	0.3738	0.061*
H18B	0.5457	0.0501	0.4423	0.061*
H18C	0.6425	0.1550	0.4719	0.061*
C19	−0.12248 (12)	0.07969 (11)	0.39365 (9)	0.0327 (3)
H19A	−0.1567	0.0476	0.3307	0.049*
H19B	−0.1853	0.1381	0.3949	0.049*
H19C	−0.1199	0.0247	0.4399	0.049*
C20	0.27302 (13)	0.02042 (10)	0.32129 (9)	0.0320 (3)
H20A	0.1915	−0.0152	0.2742	0.048*
H20B	0.3352	−0.0337	0.3631	0.048*
H20C	0.3237	0.0603	0.2895	0.048*
H3	0.0349 (17)	0.0442 (14)	0.3127 (12)	0.041 (4)*
H2A	0.1834 (19)	0.5891 (15)	0.3761 (12)	0.052 (5)*
H3B	0.708 (2)	0.2444 (15)	0.1288 (13)	0.052 (5)*
H3C	0.8389 (19)	0.2649 (16)	0.1352 (12)	0.051 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0411 (5)	0.0483 (6)	0.0488 (6)	−0.0131 (4)	0.0291 (4)	−0.0137 (4)
O2	0.0226 (4)	0.0535 (6)	0.0444 (5)	0.0012 (4)	0.0046 (4)	−0.0123 (5)
O3	0.0288 (4)	0.0270 (5)	0.0379 (5)	0.0030 (3)	0.0118 (4)	0.0019 (3)
N1	0.0339 (5)	0.0258 (5)	0.0265 (5)	0.0009 (4)	0.0034 (4)	0.0030 (4)
N2	0.0321 (5)	0.0202 (5)	0.0278 (5)	−0.0003 (4)	0.0068 (4)	0.0030 (4)
N3	0.0256 (5)	0.0228 (5)	0.0229 (4)	−0.0016 (4)	0.0066 (4)	−0.0041 (3)
C1	0.0336 (6)	0.0220 (5)	0.0258 (5)	−0.0059 (4)	0.0098 (4)	0.0007 (4)
C2	0.0586 (9)	0.0276 (7)	0.0334 (6)	0.0049 (6)	0.0137 (6)	−0.0011 (5)
C3	0.0906 (13)	0.0282 (7)	0.0366 (7)	−0.0079 (7)	0.0256 (8)	−0.0070 (6)
C4	0.0712 (11)	0.0577 (10)	0.0309 (6)	−0.0320 (9)	0.0153 (7)	−0.0133 (7)
C5	0.0375 (8)	0.0912 (14)	0.0410 (8)	−0.0132 (8)	0.0014 (6)	−0.0141 (9)
C6	0.0315 (6)	0.0564 (9)	0.0376 (7)	−0.0012 (6)	0.0065 (5)	−0.0101 (6)
C7	0.0239 (5)	0.0216 (5)	0.0254 (5)	0.0004 (4)	0.0084 (4)	0.0013 (4)
C8	0.0214 (5)	0.0197 (5)	0.0227 (5)	0.0011 (4)	0.0072 (4)	0.0007 (4)
C9	0.0317 (6)	0.0227 (6)	0.0250 (5)	0.0000 (4)	0.0043 (4)	0.0006 (4)
C10	0.0202 (5)	0.0187 (5)	0.0204 (4)	0.0003 (4)	0.0055 (4)	−0.0001 (4)
C11	0.0225 (5)	0.0197 (5)	0.0234 (5)	0.0029 (4)	0.0087 (4)	0.0029 (4)
C12	0.0267 (5)	0.0196 (5)	0.0227 (5)	0.0046 (4)	0.0087 (4)	0.0034 (4)
C13	0.0230 (5)	0.0207 (5)	0.0247 (5)	0.0006 (4)	0.0080 (4)	0.0022 (4)
C14	0.0223 (5)	0.0205 (5)	0.0228 (5)	0.0008 (4)	0.0080 (4)	0.0012 (4)
C15	0.0273 (5)	0.0251 (6)	0.0271 (5)	0.0015 (4)	0.0116 (4)	−0.0003 (4)
C16	0.0427 (7)	0.0440 (8)	0.0337 (6)	−0.0104 (6)	0.0212 (5)	−0.0139 (5)
C17	0.0238 (5)	0.0244 (6)	0.0333 (6)	0.0033 (4)	0.0101 (4)	0.0046 (4)
C18	0.0289 (6)	0.0501 (8)	0.0464 (7)	0.0014 (6)	0.0195 (6)	−0.0014 (6)
C19	0.0261 (6)	0.0351 (7)	0.0352 (6)	−0.0075 (5)	0.0100 (5)	−0.0066 (5)
C20	0.0347 (6)	0.0287 (6)	0.0321 (6)	0.0065 (5)	0.0123 (5)	−0.0054 (5)

Geometric parameters (Å, º) top

O1—C15	1.2329 (15)	C8—C10	1.5133 (14)
O2—C17	1.2316 (15)	C9—H9	0.9500
O3—H3B	0.86 (2)	C10—C14	1.5219 (14)
O3—H3C	0.87 (2)	C10—C11	1.5272 (14)
N1—C9	1.3279 (16)	C10—H10	1.0000
N1—N2	1.3468 (14)	C11—C12	1.3608 (15)
N2—C7	1.3549 (14)	C11—C17	1.4649 (15)
N2—H2A	0.938 (19)	C12—C20	1.5055 (15)
N3—C13	1.3726 (14)	C13—C14	1.3646 (15)
N3—C12	1.3788 (15)	C13—C19	1.4977 (15)
N3—H3	0.878 (17)	C14—C15	1.4565 (15)
C1—C6	1.3814 (18)	C15—C16	1.5025 (16)
C1—C2	1.3931 (18)	C16—H16A	0.9800
C1—C7	1.4775 (15)	C16—H16B	0.9800
C2—C3	1.387 (2)	C16—H16C	0.9800
C2—H2	0.9500	C17—C18	1.5060 (17)
C3—C4	1.371 (3)	C18—H18A	0.9800
C3—H3A	0.9500	C18—H18B	0.9800
C4—C5	1.373 (3)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.391 (2)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.3888 (15)	C20—H20B	0.9800
C8—C9	1.4079 (14)	C20—H20C	0.9800

H3B—O3—H3C	102.1 (16)	C12—C11—C10	118.75 (9)
C9—N1—N2	104.58 (9)	C17—C11—C10	115.75 (9)
N1—N2—C7	112.61 (10)	C11—C12—N3	118.60 (10)
N1—N2—H2A	119.0 (11)	C11—C12—C20	128.90 (10)
C7—N2—H2A	127.7 (11)	N3—C12—C20	112.46 (10)
C13—N3—C12	123.31 (9)	C14—C13—N3	119.18 (10)
C13—N3—H3	117.2 (11)	C14—C13—C19	127.29 (10)
C12—N3—H3	117.3 (11)	N3—C13—C19	113.53 (10)
C6—C1—C2	118.71 (12)	C13—C14—C15	121.77 (10)
C6—C1—C7	121.70 (11)	C13—C14—C10	117.93 (9)
C2—C1—C7	119.58 (11)	C15—C14—C10	120.19 (9)
C3—C2—C1	120.69 (15)	O1—C15—C14	122.76 (11)
C3—C2—H2	119.7	O1—C15—C16	118.82 (10)
C1—C2—H2	119.7	C14—C15—C16	118.41 (10)
C4—C3—C2	120.12 (15)	C15—C16—H16A	109.5
C4—C3—H3A	119.9	C15—C16—H16B	109.5
C2—C3—H3A	119.9	H16A—C16—H16B	109.5
C3—C4—C5	119.63 (13)	C15—C16—H16C	109.5
C3—C4—H4	120.2	H16A—C16—H16C	109.5
C5—C4—H4	120.2	H16B—C16—H16C	109.5
C4—C5—C6	120.89 (16)	O2—C17—C11	118.77 (11)
C4—C5—H5	119.6	O2—C17—C18	117.87 (11)
C6—C5—H5	119.6	C11—C17—C18	123.36 (11)
C1—C6—C5	119.96 (15)	C17—C18—H18A	109.5
C1—C6—H6	120.0	C17—C18—H18B	109.5
C5—C6—H6	120.0	H18A—C18—H18B	109.5
N2—C7—C8	106.64 (9)	C17—C18—H18C	109.5
N2—C7—C1	119.24 (10)	H18A—C18—H18C	109.5
C8—C7—C1	134.00 (10)	H18B—C18—H18C	109.5
C7—C8—C9	103.89 (9)	C13—C19—H19A	109.5
C7—C8—C10	130.29 (9)	C13—C19—H19B	109.5
C9—C8—C10	125.78 (10)	H19A—C19—H19B	109.5
N1—C9—C8	112.27 (10)	C13—C19—H19C	109.5
N1—C9—H9	123.9	H19A—C19—H19C	109.5
C8—C9—H9	123.9	H19B—C19—H19C	109.5
C8—C10—C14	110.72 (8)	C12—C20—H20A	109.5
C8—C10—C11	110.53 (8)	C12—C20—H20B	109.5
C14—C10—C11	110.10 (8)	H20A—C20—H20B	109.5
C8—C10—H10	108.5	C12—C20—H20C	109.5
C14—C10—H10	108.5	H20A—C20—H20C	109.5
C11—C10—H10	108.5	H20B—C20—H20C	109.5
C12—C11—C17	125.48 (10)

C9—N1—N2—C7	1.05 (14)	C14—C10—C11—C12	33.04 (13)
C6—C1—C2—C3	0.0 (2)	C8—C10—C11—C17	91.88 (11)
C7—C1—C2—C3	−178.86 (13)	C14—C10—C11—C17	−145.49 (9)
C1—C2—C3—C4	0.5 (2)	C17—C11—C12—N3	169.86 (10)
C2—C3—C4—C5	−0.5 (2)	C10—C11—C12—N3	−8.51 (15)
C3—C4—C5—C6	−0.1 (3)	C17—C11—C12—C20	−7.34 (18)
C2—C1—C6—C5	−0.6 (2)	C10—C11—C12—C20	174.29 (10)
C7—C1—C6—C5	178.25 (14)	C13—N3—C12—C11	−18.40 (16)
C4—C5—C6—C1	0.7 (3)	C13—N3—C12—C20	159.25 (10)
N1—N2—C7—C8	−0.31 (13)	C12—N3—C13—C14	16.24 (16)
N1—N2—C7—C1	−176.91 (10)	C12—N3—C13—C19	−163.95 (10)
C6—C1—C7—N2	−128.63 (13)	N3—C13—C14—C15	−171.08 (10)
C2—C1—C7—N2	50.24 (16)	C19—C13—C14—C15	9.13 (18)
C6—C1—C7—C8	55.9 (2)	N3—C13—C14—C10	12.63 (15)
C2—C1—C7—C8	−125.23 (15)	C19—C13—C14—C10	−167.15 (11)
N2—C7—C8—C9	−0.53 (12)	C8—C10—C14—C13	87.54 (12)
C1—C7—C8—C9	175.35 (13)	C11—C10—C14—C13	−34.99 (13)
N2—C7—C8—C10	−178.25 (10)	C8—C10—C14—C15	−88.80 (11)
C1—C7—C8—C10	−2.4 (2)	C11—C10—C14—C15	148.67 (10)
N2—N1—C9—C8	−1.40 (14)	C13—C14—C15—O1	5.77 (18)
C7—C8—C9—N1	1.23 (14)	C10—C14—C15—O1	−178.02 (11)
C10—C8—C9—N1	179.10 (10)	C13—C14—C15—C16	−175.47 (11)
C7—C8—C10—C14	119.14 (12)	C10—C14—C15—C16	0.73 (16)
C9—C8—C10—C14	−58.14 (14)	C12—C11—C17—O2	−160.83 (12)
C7—C8—C10—C11	−118.59 (12)	C10—C11—C17—O2	17.58 (16)
C9—C8—C10—C11	64.13 (14)	C12—C11—C17—C18	19.51 (18)
C8—C10—C11—C12	−89.60 (11)	C10—C11—C17—C18	−162.08 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.938 (19)	1.855 (19)	2.7822 (14)	169.1 (16)
N3—H3···N1ⁱⁱ	0.878 (17)	2.075 (17)	2.9454 (13)	171.1 (15)
O3—H3B···O2ⁱⁱⁱ	0.86 (2)	1.92 (2)	2.7838 (13)	175.8 (17)
O3—H3C···O1^iv	0.87 (2)	1.88 (2)	2.7372 (14)	169.8 (18)
C6—H6···O2	0.95	2.44	3.282 (2)	148
C10—H10···O2	1.00	2.33	2.7624 (13)	105

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃O₂·H₂O
M_r	353.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	10.3516 (2), 12.4352 (3), 15.4101 (3)
β (°)	112.798 (1)
V (Å³)	1828.68 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.41 × 0.34 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.965, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	17882, 4559, 3849
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.04
No. of reflections	4559
No. of parameters	255
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.938 (19)	1.855 (19)	2.7822 (14)	169.1 (16)
N3—H3···N1ⁱⁱ	0.878 (17)	2.075 (17)	2.9454 (13)	171.1 (15)
O3—H3B···O2ⁱⁱⁱ	0.86 (2)	1.92 (2)	2.7838 (13)	175.8 (17)
O3—H3C···O1^iv	0.87 (2)	1.88 (2)	2.7372 (14)	169.8 (18)
C6—H6···O2	0.95	2.44	3.282 (2)	148.1
C10—H10···O2	1.00	2.33	2.7624 (13)	105.3

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z−1/2.

Acknowledgements

AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, and the Government of India for a Young Scientist award.

References

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Volume 68| Part 11| November 2012| Pages o3156-o3157

doi:10.1107/S1600536812042614

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[5-Acetyl-2,6-di­methyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4-di­hydro­pyridin-3-yl]ethanone monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

1-[5-Acetyl-2,6-dimethyl-4-(5-phenyl-1H-pyrazol-3-yl)-1,4-dihydropyridin-3-yl]ethanone monohydrate