1,1'-[4-(4-Methoxy-phen-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-di-yl]diethanone.

In the title compound, C(18)H(21)NO(3), which belongs to the family of calcium channel blockers, the dihydropyridine ring assumes a flattened boat conformation. The two carbonyl units adopt a synperiplanar conformation with respect to the double bonds in the dihydro-pyridine ring. The methoxy-phenyl ring is almost perpendicular to the prydine ring [dihedral angle = 89.01 (7)°]. In the crystal, the mol-ecules are connected by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background, see: Ganjali et al. (2007 ▶); Xia et al. (2005 ▶). For hybridization, see: Beddoes et al.(1986 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C18H21NO3

M = 299.36

Orthorhombic,

a = 12.0781 (3) Å

b = 8.9650 (2) Å

c = 29.3755 (8) Å

V = 3180.78 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.979, T max = 0.983

36021 measured reflections

4055 independent reflections

2828 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 1.05

4055 reflections

208 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041592/bt5060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041592/bt5060Isup2.hkl

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

C18H21NO3	F(000) = 1280
Mr = 299.36	Dx = 1.250 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4055 reflections
a = 12.0781 (3) Å	θ = 1.4–28.6°
b = 8.9650 (2) Å	µ = 0.09 mm−1
c = 29.3755 (8) Å	T = 293 K
V = 3180.78 (14) Å3	Block, light yellow
Z = 8	0.25 × 0.20 × 0.20 mm

Bruker Kappa APEXII area-detector diffractometer	4055 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scans	θmax = 28.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −16→14
Tmin = 0.979, Tmax = 0.983	k = −12→10
36021 measured reflections	l = −37→39

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0637P)2 + 1.0129P] where P = (Fo2 + 2Fc2)/3
4055 reflections	(Δ/σ)max = 0.003
208 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C2	0.52089 (13)	0.12861 (18)	0.28911 (5)	0.0418 (4)
C3	0.60545 (12)	0.18029 (17)	0.31531 (5)	0.0392 (3)
C4	0.57919 (12)	0.24866 (17)	0.36162 (5)	0.0378 (3)
H4	0.6343	0.3265	0.3675	0.045*
C5	0.46584 (13)	0.32299 (17)	0.36102 (5)	0.0409 (3)
C6	0.38706 (12)	0.27123 (18)	0.33254 (5)	0.0422 (3)
C7	0.52978 (15)	0.0360 (2)	0.24679 (6)	0.0595 (5)
H7A	0.5613	0.0949	0.2228	0.089*
H7B	0.4574	0.0025	0.2379	0.089*
H7C	0.5763	−0.0487	0.2526	0.089*
C8	0.72005 (13)	0.1649 (2)	0.30089 (6)	0.0487 (4)
C9	0.81050 (15)	0.2381 (3)	0.32811 (8)	0.0741 (6)
H9A	0.8186	0.1875	0.3567	0.111*
H9B	0.7918	0.3407	0.3334	0.111*
H9C	0.8789	0.2327	0.3115	0.111*
C10	0.59067 (12)	0.13184 (16)	0.39902 (5)	0.0368 (3)
C11	0.67301 (14)	0.14207 (18)	0.43151 (5)	0.0460 (4)
H11	0.7216	0.2225	0.4304	0.055*
C12	0.68580 (14)	0.03681 (19)	0.46561 (5)	0.0486 (4)
H12	0.7423	0.0467	0.4869	0.058*
C13	0.61449 (13)	−0.08222 (17)	0.46774 (5)	0.0438 (4)
C14	0.53161 (14)	−0.09579 (19)	0.43563 (6)	0.0478 (4)
H14	0.4833	−0.1765	0.4368	0.057*
C15	0.52023 (13)	0.00946 (17)	0.40189 (5)	0.0434 (4)
H15	0.4641	−0.0015	0.3805	0.052*
C16	0.70171 (18)	−0.1747 (2)	0.53459 (6)	0.0664 (5)
H16A	0.7741	−0.1742	0.5211	0.100*
H16B	0.6964	−0.2558	0.5558	0.100*
H16C	0.6895	−0.0822	0.5502	0.100*
C17	0.44451 (17)	0.44728 (19)	0.39277 (6)	0.0547 (5)
C18	0.5199 (2)	0.4709 (2)	0.43225 (7)	0.0728 (6)
H18A	0.4905	0.5480	0.4514	0.109*
H18B	0.5918	0.5000	0.4214	0.109*
H18C	0.5261	0.3800	0.4493	0.109*
C19	0.26738 (14)	0.3160 (2)	0.33045 (7)	0.0589 (5)
H19A	0.2469	0.3640	0.3584	0.088*
H19B	0.2224	0.2289	0.3261	0.088*
H19C	0.2564	0.3837	0.3055	0.088*
N1	0.41402 (11)	0.16250 (16)	0.30102 (5)	0.0441 (3)
O1	0.74715 (11)	0.09406 (19)	0.26662 (4)	0.0754 (5)
O2	0.62054 (12)	−0.19260 (14)	0.49995 (4)	0.0596 (4)
O3	0.36634 (16)	0.5314 (2)	0.38831 (6)	0.1011 (6)
H1	0.3631 (16)	0.135 (2)	0.2819 (6)	0.057 (5)*

	U11	U22	U33	U12	U13	U23
C2	0.0386 (8)	0.0492 (9)	0.0374 (7)	0.0028 (7)	0.0024 (6)	0.0020 (6)
C3	0.0345 (7)	0.0462 (8)	0.0370 (7)	0.0005 (6)	0.0022 (6)	0.0023 (6)
C4	0.0386 (7)	0.0384 (8)	0.0364 (7)	−0.0017 (6)	0.0021 (6)	0.0010 (6)
C5	0.0446 (8)	0.0388 (8)	0.0393 (7)	0.0045 (6)	0.0071 (6)	0.0067 (6)
C6	0.0384 (7)	0.0456 (9)	0.0426 (8)	0.0069 (6)	0.0071 (6)	0.0113 (6)
C7	0.0497 (10)	0.0809 (13)	0.0479 (9)	0.0060 (9)	−0.0051 (8)	−0.0174 (9)
C8	0.0378 (8)	0.0648 (11)	0.0435 (8)	−0.0005 (7)	0.0069 (7)	0.0053 (8)
C9	0.0388 (9)	0.1061 (17)	0.0773 (13)	−0.0135 (11)	0.0059 (9)	−0.0123 (13)
C10	0.0387 (8)	0.0364 (7)	0.0351 (7)	0.0025 (6)	0.0030 (6)	−0.0027 (6)
C11	0.0473 (9)	0.0436 (8)	0.0470 (9)	−0.0054 (7)	−0.0054 (7)	0.0002 (7)
C12	0.0517 (9)	0.0502 (9)	0.0440 (8)	0.0015 (8)	−0.0097 (7)	0.0014 (7)
C13	0.0490 (9)	0.0414 (8)	0.0410 (8)	0.0093 (7)	0.0043 (7)	0.0038 (7)
C14	0.0475 (9)	0.0407 (8)	0.0552 (9)	−0.0036 (7)	0.0007 (7)	0.0042 (7)
C15	0.0416 (8)	0.0432 (8)	0.0454 (8)	−0.0025 (7)	−0.0051 (6)	0.0006 (7)
C16	0.0765 (13)	0.0739 (13)	0.0488 (10)	0.0138 (11)	−0.0043 (9)	0.0162 (9)
C17	0.0683 (12)	0.0430 (9)	0.0529 (10)	0.0123 (8)	0.0117 (8)	0.0041 (7)
C18	0.0929 (16)	0.0552 (11)	0.0704 (13)	0.0078 (11)	−0.0053 (11)	−0.0226 (10)
C19	0.0413 (9)	0.0695 (12)	0.0660 (11)	0.0145 (8)	0.0062 (8)	0.0108 (9)
N1	0.0335 (7)	0.0551 (8)	0.0438 (7)	0.0018 (6)	−0.0028 (6)	−0.0005 (6)
O1	0.0454 (7)	0.1195 (12)	0.0613 (8)	−0.0014 (8)	0.0170 (6)	−0.0231 (8)
O2	0.0696 (8)	0.0534 (7)	0.0559 (7)	0.0045 (6)	−0.0023 (6)	0.0167 (6)
O3	0.1203 (14)	0.0915 (12)	0.0916 (12)	0.0615 (11)	−0.0129 (10)	−0.0239 (10)

C2—C3	1.360 (2)	C11—C12	1.385 (2)
C2—N1	1.3715 (19)	C11—H11	0.9300
C2—C7	1.499 (2)	C12—C13	1.373 (2)
C3—C8	1.454 (2)	C12—H12	0.9300
C3—C4	1.526 (2)	C13—O2	1.3711 (19)
C4—C5	1.523 (2)	C13—C14	1.381 (2)
C4—C10	1.524 (2)	C14—C15	1.375 (2)
C4—H4	0.9800	C14—H14	0.9300
C5—C6	1.349 (2)	C15—H15	0.9300
C5—C17	1.476 (2)	C16—O2	1.422 (2)
C6—N1	1.383 (2)	C16—H16A	0.9600
C6—C19	1.502 (2)	C16—H16B	0.9600
C7—H7A	0.9600	C16—H16C	0.9600
C7—H7B	0.9600	C17—O3	1.216 (2)
C7—H7C	0.9600	C17—C18	1.490 (3)
C8—O1	1.234 (2)	C18—H18A	0.9600
C8—C9	1.504 (3)	C18—H18B	0.9600
C9—H9A	0.9600	C18—H18C	0.9600
C9—H9B	0.9600	C19—H19A	0.9600
C9—H9C	0.9600	C19—H19B	0.9600
C10—C11	1.381 (2)	C19—H19C	0.9600
C10—C15	1.391 (2)	N1—H1	0.869 (19)
C3—C2—N1	119.13 (14)	C12—C11—H11	118.8
C3—C2—C7	127.17 (14)	C13—C12—C11	119.51 (15)
N1—C2—C7	113.69 (14)	C13—C12—H12	120.2
C2—C3—C8	121.17 (14)	C11—C12—H12	120.2
C2—C3—C4	119.04 (13)	O2—C13—C12	123.99 (15)
C8—C3—C4	119.72 (13)	O2—C13—C14	116.52 (15)
C5—C4—C10	113.01 (12)	C12—C13—C14	119.49 (15)
C5—C4—C3	110.63 (12)	C15—C14—C13	120.29 (15)
C10—C4—C3	110.35 (12)	C15—C14—H14	119.9
C5—C4—H4	107.5	C13—C14—H14	119.9
C10—C4—H4	107.5	C14—C15—C10	121.58 (14)
C3—C4—H4	107.5	C14—C15—H15	119.2
C6—C5—C17	121.90 (15)	C10—C15—H15	119.2
C6—C5—C4	119.39 (14)	O2—C16—H16A	109.5
C17—C5—C4	118.68 (15)	O2—C16—H16B	109.5
C5—C6—N1	119.43 (14)	H16A—C16—H16B	109.5
C5—C6—C19	127.76 (16)	O2—C16—H16C	109.5
N1—C6—C19	112.80 (15)	H16A—C16—H16C	109.5
C2—C7—H7A	109.5	H16B—C16—H16C	109.5
C2—C7—H7B	109.5	O3—C17—C5	122.42 (18)
H7A—C7—H7B	109.5	O3—C17—C18	118.06 (17)
C2—C7—H7C	109.5	C5—C17—C18	119.51 (16)
H7A—C7—H7C	109.5	C17—C18—H18A	109.5
H7B—C7—H7C	109.5	C17—C18—H18B	109.5
O1—C8—C3	122.60 (16)	H18A—C18—H18B	109.5
O1—C8—C9	117.72 (15)	C17—C18—H18C	109.5
C3—C8—C9	119.67 (15)	H18A—C18—H18C	109.5
C8—C9—H9A	109.5	H18B—C18—H18C	109.5
C8—C9—H9B	109.5	C6—C19—H19A	109.5
H9A—C9—H9B	109.5	C6—C19—H19B	109.5
C8—C9—H9C	109.5	H19A—C19—H19B	109.5
H9A—C9—H9C	109.5	C6—C19—H19C	109.5
H9B—C9—H9C	109.5	H19A—C19—H19C	109.5
C11—C10—C15	116.79 (14)	H19B—C19—H19C	109.5
C11—C10—C4	121.19 (13)	C2—N1—C6	123.26 (14)
C15—C10—C4	122.01 (13)	C2—N1—H1	116.0 (13)
C10—C11—C12	122.34 (15)	C6—N1—H1	117.8 (13)
C10—C11—H11	118.8	C13—O2—C16	116.70 (14)
N1—C2—C3—C8	−171.57 (15)	C5—C4—C10—C15	58.19 (18)
C7—C2—C3—C8	8.0 (3)	C3—C4—C10—C15	−66.27 (18)
N1—C2—C3—C4	11.4 (2)	C15—C10—C11—C12	−0.2 (2)
C7—C2—C3—C4	−169.03 (16)	C4—C10—C11—C12	−179.46 (15)
C2—C3—C4—C5	−30.7 (2)	C10—C11—C12—C13	−0.3 (3)
C8—C3—C4—C5	152.27 (14)	C11—C12—C13—O2	179.63 (15)
C2—C3—C4—C10	95.13 (17)	C11—C12—C13—C14	0.5 (2)
C8—C3—C4—C10	−81.92 (18)	O2—C13—C14—C15	−179.49 (15)
C10—C4—C5—C6	−95.93 (16)	C12—C13—C14—C15	−0.3 (2)
C3—C4—C5—C6	28.38 (19)	C13—C14—C15—C10	−0.2 (2)
C10—C4—C5—C17	82.28 (17)	C11—C10—C15—C14	0.4 (2)
C3—C4—C5—C17	−153.41 (14)	C4—C10—C15—C14	179.66 (14)
C17—C5—C6—N1	174.94 (14)	C6—C5—C17—O3	−17.3 (3)
C4—C5—C6—N1	−6.9 (2)	C4—C5—C17—O3	164.55 (19)
C17—C5—C6—C19	−5.9 (3)	C6—C5—C17—C18	161.94 (18)
C4—C5—C6—C19	172.25 (15)	C4—C5—C17—C18	−16.2 (2)
C2—C3—C8—O1	−6.3 (3)	C3—C2—N1—C6	13.9 (2)
C4—C3—C8—O1	170.70 (16)	C7—C2—N1—C6	−165.71 (15)
C2—C3—C8—C9	173.28 (18)	C5—C6—N1—C2	−16.4 (2)
C4—C3—C8—C9	−9.7 (2)	C19—C6—N1—C2	164.36 (15)
C5—C4—C10—C11	−122.56 (16)	C12—C13—O2—C16	4.3 (2)
C3—C4—C10—C11	112.98 (16)	C14—C13—O2—C16	−176.55 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.869 (19)	2.03 (2)	2.8961 (19)	173.1 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.869 (19)	2.03 (2)	2.8961 (19)	173.1 (18)

Symmetry code: (i) .