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

In the title compound, C(20)H(21)N(3)O(2)·H(2)O, the aza-substitued six-membered ring adopts a (L4)B 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. Intra-molecular 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 = 353.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.04

4559 reflections

255 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042614/hg5260sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042614/hg5260Isup2.cdx

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042614/hg5260Isup4.cml

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

C20H21N3O2·H2O	F(000) = 752
Mr = 353.41	Dx = 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

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

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(Fo2) + (0.0577P)2 + 0.5735P] where P = (Fo2 + 2Fc2)/3
4559 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	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

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⋯O1iv	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) ; (ii) ; (iii) ; (iv) .