1,1'-[4-(2-Methoxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-diyl]diethanone.

In the title compound, C(18)H(21)NO(3), the 1,4-dihydro-pyridine ring exhibits a flattened boat conformation. The methoxy-phenyl ring is nearly planar [r.m.s. deviation = 0.0723 (1) Å] and is perpendicular to the base of the boat [dihedral angle = 88.98 (4)°]. Inter-molecular N-H⋯O and C-H⋯O hydrogen bonds exist in the crystal structure.

Related literature

For the biological importance of the 1,4-dihydro­pyridine ring, see: Gaudio et al. (1994 ▶); Böcker & Guengerich, (1986 ▶); Gordeev et al. (1996 ▶); Vo et al. (1995 ▶); Cooper et al. (1992 ▶). For hydrogen-bonding inter­actions, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H21NO3

M = 299.36

Monoclinic,

a = 26.5512 (6) Å

b = 7.5077 (1) Å

c = 17.0818 (3) Å

β = 114.904 (1)°

V = 3088.44 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.19 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.984, T max = 0.987

21137 measured reflections

4722 independent reflections

3203 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.154

S = 1.05

4722 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042895/ez2191sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042895/ez2191Isup2.hkl

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

C18H21NO3	F(000) = 1280
Mr = 299.36	Dx = 1.288 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2500 reflections
a = 26.5512 (6) Å	θ = 2–30°
b = 7.5077 (1) Å	µ = 0.09 mm−1
c = 17.0818 (3) Å	T = 293 K
β = 114.904 (1)°	Block, colourless
V = 3088.44 (10) Å3	0.19 × 0.17 × 0.15 mm
Z = 8

Bruker SMART APEX CCD diffractometer	4722 independent reflections
Radiation source: fine-focus sealed tube	3203 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω–scans	θmax = 30.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −37→37
Tmin = 0.984, Tmax = 0.987	k = −10→9
21137 measured reflections	l = −23→24

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0675P)2 + 1.5117P] where P = (Fo2 + 2Fc2)/3
4722 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
H1	0.0342 (8)	0.604 (3)	0.1642 (13)	0.057 (6)*
C2	0.01518 (6)	0.35160 (18)	0.13007 (9)	0.0323 (3)
C3	0.03718 (6)	0.18412 (16)	0.14901 (8)	0.0281 (3)
C4	0.09866 (6)	0.16431 (16)	0.20952 (8)	0.0269 (3)
H4	0.1037	0.0490	0.2387	0.032*
C5	0.11627 (6)	0.30983 (18)	0.27839 (8)	0.0303 (3)
C6	0.09083 (7)	0.47109 (18)	0.25781 (9)	0.0347 (3)
C7	0.10550 (9)	0.6384 (2)	0.31085 (12)	0.0535 (5)
H7A	0.0815	0.6513	0.3396	0.080*
H7B	0.1011	0.7391	0.2739	0.080*
H7C	0.1434	0.6319	0.3530	0.080*
C8	−0.03908 (7)	0.4093 (2)	0.05923 (11)	0.0460 (4)
H8A	−0.0468	0.3383	0.0087	0.069*
H8B	−0.0368	0.5324	0.0459	0.069*
H8C	−0.0683	0.3940	0.0778	0.069*
C9	−0.05561 (8)	0.0130 (2)	0.06598 (14)	0.0566 (5)
H9A	−0.0653	0.0526	0.0080	0.085*
H9B	−0.0726	0.0897	0.0929	0.085*
H9C	−0.0686	−0.1067	0.0650	0.085*
C10	0.00627 (6)	0.01838 (18)	0.11610 (9)	0.0336 (3)
C11	0.16218 (7)	0.2748 (2)	0.36344 (10)	0.0389 (3)
C12	0.19213 (7)	0.1016 (2)	0.37945 (10)	0.0468 (4)
H12A	0.2249	0.1077	0.4328	0.070*
H12B	0.2024	0.0768	0.3330	0.070*
H12C	0.1684	0.0085	0.3829	0.070*
C13	0.13442 (6)	0.16523 (18)	0.15858 (8)	0.0300 (3)
C14	0.13751 (7)	0.3174 (2)	0.11442 (9)	0.0386 (3)
H14	0.1178	0.4182	0.1167	0.046*
C15	0.16912 (8)	0.3240 (3)	0.06698 (11)	0.0512 (4)
H15	0.1706	0.4278	0.0383	0.061*
C16	0.19800 (8)	0.1756 (3)	0.06301 (12)	0.0568 (5)
H16	0.2191	0.1787	0.0313	0.068*
C17	0.19603 (8)	0.0222 (3)	0.10549 (12)	0.0512 (4)
H17	0.2156	−0.0779	0.1020	0.061*
C18	0.16491 (6)	0.0155 (2)	0.15384 (10)	0.0376 (3)
C19	0.20059 (10)	−0.2704 (3)	0.21025 (18)	0.0742 (7)
H19A	0.1934	−0.3245	0.1556	0.111*
H19B	0.1972	−0.3585	0.2485	0.111*
H19C	0.2375	−0.2220	0.2348	0.111*
N1	0.04566 (6)	0.49206 (16)	0.17923 (8)	0.0379 (3)
O1	0.03123 (5)	−0.12395 (14)	0.13193 (9)	0.0566 (4)
O2	0.16203 (5)	−0.13353 (15)	0.19817 (8)	0.0498 (3)
O3	0.17653 (7)	0.3810 (2)	0.42269 (9)	0.0909 (6)

	U11	U22	U33	U12	U13	U23
C2	0.0344 (7)	0.0271 (6)	0.0361 (7)	0.0036 (5)	0.0156 (6)	0.0036 (5)
C3	0.0280 (7)	0.0241 (6)	0.0309 (6)	0.0009 (5)	0.0113 (5)	0.0010 (5)
C4	0.0284 (6)	0.0228 (5)	0.0282 (6)	0.0007 (5)	0.0106 (5)	0.0012 (4)
C5	0.0337 (7)	0.0288 (6)	0.0300 (6)	−0.0035 (5)	0.0151 (6)	−0.0026 (5)
C6	0.0457 (9)	0.0275 (6)	0.0341 (7)	−0.0048 (6)	0.0201 (7)	−0.0025 (5)
C7	0.0843 (14)	0.0299 (7)	0.0480 (9)	−0.0072 (8)	0.0295 (10)	−0.0090 (7)
C8	0.0389 (9)	0.0404 (8)	0.0526 (9)	0.0123 (7)	0.0131 (7)	0.0094 (7)
C9	0.0359 (9)	0.0457 (9)	0.0747 (13)	−0.0091 (7)	0.0100 (9)	−0.0078 (9)
C10	0.0327 (7)	0.0281 (6)	0.0371 (7)	−0.0018 (5)	0.0119 (6)	−0.0002 (5)
C11	0.0363 (8)	0.0468 (8)	0.0329 (7)	−0.0009 (7)	0.0139 (6)	−0.0057 (6)
C12	0.0450 (9)	0.0475 (9)	0.0361 (8)	0.0033 (7)	0.0056 (7)	0.0043 (7)
C13	0.0266 (7)	0.0340 (7)	0.0268 (6)	−0.0012 (5)	0.0085 (5)	−0.0027 (5)
C14	0.0392 (8)	0.0424 (8)	0.0336 (7)	−0.0014 (6)	0.0149 (6)	0.0030 (6)
C15	0.0555 (11)	0.0641 (11)	0.0377 (8)	−0.0147 (9)	0.0231 (8)	0.0014 (7)
C16	0.0535 (11)	0.0810 (14)	0.0478 (10)	−0.0131 (10)	0.0329 (9)	−0.0147 (9)
C17	0.0432 (10)	0.0629 (11)	0.0534 (10)	−0.0005 (8)	0.0262 (8)	−0.0162 (8)
C18	0.0326 (8)	0.0416 (8)	0.0358 (7)	0.0017 (6)	0.0117 (6)	−0.0070 (6)
C19	0.0605 (13)	0.0437 (10)	0.121 (2)	0.0168 (9)	0.0409 (14)	0.0013 (11)
N1	0.0481 (8)	0.0208 (5)	0.0426 (7)	0.0047 (5)	0.0170 (6)	0.0023 (5)
O1	0.0459 (7)	0.0242 (5)	0.0809 (9)	−0.0005 (5)	0.0083 (6)	−0.0021 (5)
O2	0.0494 (7)	0.0395 (6)	0.0653 (8)	0.0147 (5)	0.0288 (6)	0.0060 (5)
O3	0.0914 (12)	0.0885 (11)	0.0508 (8)	0.0342 (9)	−0.0110 (8)	−0.0358 (8)

C2—C3	1.3667 (18)	C10—O1	1.2260 (17)
C2—N1	1.3783 (19)	C11—O3	1.2166 (19)
C2—C8	1.503 (2)	C11—C12	1.488 (2)
C3—C10	1.4662 (18)	C12—H12A	0.9600
C3—C4	1.5278 (18)	C12—H12B	0.9600
C4—C5	1.5274 (17)	C12—H12C	0.9600
C4—C13	1.5346 (19)	C13—C14	1.390 (2)
C4—H4	0.9800	C13—C18	1.407 (2)
C5—C6	1.358 (2)	C14—C15	1.392 (2)
C5—C11	1.475 (2)	C14—H14	0.9300
C6—N1	1.382 (2)	C15—C16	1.371 (3)
C6—C7	1.501 (2)	C15—H15	0.9300
C7—H7A	0.9600	C16—C17	1.374 (3)
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	C17—C18	1.394 (2)
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—O2	1.3708 (19)
C8—H8C	0.9600	C19—O2	1.403 (2)
C9—C10	1.500 (2)	C19—H19A	0.9600
C9—H9A	0.9600	C19—H19B	0.9600
C9—H9B	0.9600	C19—H19C	0.9600
C9—H9C	0.9600	N1—H1	0.89 (2)
C3—C2—N1	118.48 (13)	C3—C10—C9	122.92 (13)
C3—C2—C8	128.68 (13)	O3—C11—C5	122.83 (15)
N1—C2—C8	112.82 (12)	O3—C11—C12	117.63 (15)
C2—C3—C10	125.14 (13)	C5—C11—C12	119.53 (13)
C2—C3—C4	118.56 (11)	C11—C12—H12A	109.5
C10—C3—C4	116.29 (11)	C11—C12—H12B	109.5
C5—C4—C3	110.16 (11)	H12A—C12—H12B	109.5
C5—C4—C13	111.83 (11)	C11—C12—H12C	109.5
C3—C4—C13	110.85 (10)	H12A—C12—H12C	109.5
C5—C4—H4	108.0	H12B—C12—H12C	109.5
C3—C4—H4	108.0	C14—C13—C18	117.30 (13)
C13—C4—H4	108.0	C14—C13—C4	120.21 (12)
C6—C5—C11	121.91 (13)	C18—C13—C4	122.49 (12)
C6—C5—C4	118.72 (12)	C13—C14—C15	122.19 (16)
C11—C5—C4	119.29 (12)	C13—C14—H14	118.9
C5—C6—N1	119.11 (12)	C15—C14—H14	118.9
C5—C6—C7	127.97 (15)	C16—C15—C14	119.16 (17)
N1—C6—C7	112.92 (13)	C16—C15—H15	120.4
C6—C7—H7A	109.5	C14—C15—H15	120.4
C6—C7—H7B	109.5	C15—C16—C17	120.58 (16)
H7A—C7—H7B	109.5	C15—C16—H16	119.7
C6—C7—H7C	109.5	C17—C16—H16	119.7
H7A—C7—H7C	109.5	C16—C17—C18	120.49 (16)
H7B—C7—H7C	109.5	C16—C17—H17	119.8
C2—C8—H8A	109.5	C18—C17—H17	119.8
C2—C8—H8B	109.5	O2—C18—C17	122.79 (14)
H8A—C8—H8B	109.5	O2—C18—C13	116.94 (13)
C2—C8—H8C	109.5	C17—C18—C13	120.26 (15)
H8A—C8—H8C	109.5	O2—C19—H19A	109.5
H8B—C8—H8C	109.5	O2—C19—H19B	109.5
C10—C9—H9A	109.5	H19A—C19—H19B	109.5
C10—C9—H9B	109.5	O2—C19—H19C	109.5
H9A—C9—H9B	109.5	H19A—C19—H19C	109.5
C10—C9—H9C	109.5	H19B—C19—H19C	109.5
H9A—C9—H9C	109.5	C2—N1—C6	123.47 (12)
H9B—C9—H9C	109.5	C2—N1—H1	120.1 (13)
O1—C10—C3	119.46 (13)	C6—N1—H1	116.0 (13)
O1—C10—C9	117.58 (13)	C18—O2—C19	118.17 (15)
N1—C2—C3—C10	166.44 (14)	C4—C5—C11—C12	2.6 (2)
C8—C2—C3—C10	−15.2 (2)	C5—C4—C13—C14	−57.93 (16)
N1—C2—C3—C4	−13.2 (2)	C3—C4—C13—C14	65.43 (16)
C8—C2—C3—C4	165.14 (14)	C5—C4—C13—C18	122.36 (14)
C2—C3—C4—C5	34.57 (16)	C3—C4—C13—C18	−114.29 (14)
C10—C3—C4—C5	−145.08 (12)	C18—C13—C14—C15	0.1 (2)
C2—C3—C4—C13	−89.74 (15)	C4—C13—C14—C15	−179.60 (14)
C10—C3—C4—C13	90.61 (14)	C13—C14—C15—C16	0.4 (3)
C3—C4—C5—C6	−31.67 (17)	C14—C15—C16—C17	−0.2 (3)
C13—C4—C5—C6	92.08 (15)	C15—C16—C17—C18	−0.5 (3)
C3—C4—C5—C11	151.55 (12)	C16—C17—C18—O2	−179.28 (16)
C13—C4—C5—C11	−84.71 (15)	C16—C17—C18—C13	1.0 (3)
C11—C5—C6—N1	−175.72 (13)	C14—C13—C18—O2	179.44 (13)
C4—C5—C6—N1	7.6 (2)	C4—C13—C18—O2	−0.8 (2)
C11—C5—C6—C7	4.3 (2)	C14—C13—C18—C17	−0.8 (2)
C4—C5—C6—C7	−172.37 (15)	C4—C13—C18—C17	178.91 (14)
C2—C3—C10—O1	174.28 (15)	C3—C2—N1—C6	−15.2 (2)
C4—C3—C10—O1	−6.1 (2)	C8—C2—N1—C6	166.19 (14)
C2—C3—C10—C9	−8.1 (2)	C5—C6—N1—C2	18.3 (2)
C4—C3—C10—C9	171.54 (15)	C7—C6—N1—C2	−161.78 (15)
C6—C5—C11—O3	7.2 (3)	C17—C18—O2—C19	13.7 (2)
C4—C5—C11—O3	−176.16 (17)	C13—C18—O2—C19	−166.57 (17)
C6—C5—C11—C12	−174.06 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (2)	2.11 (2)	2.9749 (16)	163 (2)
C7—H7B···O1i	0.96	2.57	3.367 (2)	141
C15—H15···O3ii	0.93	2.50	3.381 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89 (2)	2.11 (2)	2.9749 (16)	163 (2)
C7—H7B⋯O1i	0.96	2.57	3.367 (2)	141
C15—H15⋯O3ii	0.93	2.50	3.381 (2)	158

Symmetry codes: (i) ; (ii) .