1,1'-[4-(2,4-Dichloro-phen-yl)-2,6-di-methyl-1,4-di-hydro-pyridine-3,5-di-yl]diethanone.

In the title compound, C(17)H(17)Cl(2)NO(2), the central 1,4-dihydro-pyridine ring adopts a flattened-boat conformation. The ethanone substituents of the dihydro-pyridine ring at positions 3 and 5 have synperiplanar (cis) or anti-periplanar (trans) conformations with respect to the adjacent C=C bonds in the dihydro-pyridine ring. The 2,4-dichloro-phenyl ring is almost planar [r.m.s. deviation = 0.0045 (1) Å] and almost perpendicular [89.27 (3)°] to the mean plane of the dihydro-pyridine ring. In the crystal, an N-H⋯O hydrogen bond links mol-ecules into a zigzag chain along the ac diagonal. C-H⋯Cl contacts form centrosymmetric dimers and additional weak C-H⋯O contacts further consolidate the packing.

Related literature

For background to the pharmaceutical applications of 1,4-dihydro­pyridine derivatives, see: Rose (1989 ▶, 1990 ▶); Salehi & Guo (2004 ▶). For structure–activity relationships among 1,4-dihydro­pyridines, see: Triggle et al. (1980 ▶); Janis & Triggle (1984 ▶); Langs & Triggle (1985 ▶).

Experimental

Crystal data

C17H17Cl2NO2

M = 338.22

Monoclinic,

a = 10.307 (4) Å

b = 13.745 (3) Å

c = 11.312 (2) Å

β = 93.80 (2)°

V = 1599.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.23 × 0.21 × 0.18 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.910, T max = 0.929

3247 measured reflections

2811 independent reflections

2265 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.05

2811 reflections

207 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ▶); 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/S1600536810052839/sj5076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052839/sj5076Isup2.hkl

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

C17H17Cl2NO2	F(000) = 704
Mr = 338.22	Dx = 1.405 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.307 (4) Å	θ = 2–25°
b = 13.745 (3) Å	µ = 0.41 mm−1
c = 11.312 (2) Å	T = 293 K
β = 93.80 (2)°	Block, colourless
V = 1599.0 (8) Å3	0.23 × 0.21 × 0.18 mm
Z = 4

Nonius MACH3 diffractometer	2265 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 25.0°, θmin = 2.3°
ω–2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −1→16
Tmin = 0.910, Tmax = 0.929	l = −13→13
3247 measured reflections	3 standard reflections every 60 min
2811 independent reflections	intensity decay: none

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.6776P] where P = (Fo2 + 2Fc2)/3
2811 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 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
C2	0.09331 (17)	0.23909 (14)	0.35680 (16)	0.0368 (4)
C3	0.21210 (16)	0.23609 (13)	0.41766 (15)	0.0333 (4)
C4	0.32545 (16)	0.18638 (13)	0.36213 (15)	0.0325 (4)
H4	0.3770	0.1517	0.4247	0.039*
C5	0.27979 (18)	0.11313 (13)	0.26722 (15)	0.0371 (4)
C6	0.16077 (19)	0.12296 (14)	0.21010 (16)	0.0405 (4)
C7	0.1058 (2)	0.06292 (16)	0.1077 (2)	0.0573 (6)
H7A	0.0130	0.0706	0.0998	0.069*
H7B	0.1267	−0.0043	0.1216	0.069*
H7C	0.1424	0.0841	0.0362	0.069*
C8	−0.02898 (18)	0.28757 (18)	0.3917 (2)	0.0536 (6)
H8A	−0.0961	0.2797	0.3295	0.064*
H8B	−0.0128	0.3556	0.4050	0.064*
H8C	−0.0562	0.2584	0.4631	0.064*
C9	0.24581 (18)	0.28036 (14)	0.53385 (16)	0.0388 (4)
C10	0.1592 (2)	0.34902 (17)	0.59460 (18)	0.0538 (6)
H10A	0.2028	0.3711	0.6673	0.065*
H10B	0.0803	0.3162	0.6114	0.065*
H10C	0.1390	0.4038	0.5440	0.065*
C11	0.3678 (2)	0.03428 (15)	0.23582 (19)	0.0485 (5)
C12	0.4571 (3)	−0.00851 (18)	0.3312 (2)	0.0695 (7)
H12A	0.4768	−0.0745	0.3114	0.083*
H12B	0.4159	−0.0072	0.4049	0.083*
H12C	0.5360	0.0287	0.3389	0.083*
C13	0.41271 (16)	0.26267 (13)	0.30834 (15)	0.0313 (4)
C14	0.54362 (16)	0.27779 (13)	0.34248 (15)	0.0348 (4)
C15	0.61739 (18)	0.34868 (15)	0.29079 (17)	0.0422 (5)
H15	0.7041	0.3580	0.3166	0.051*
C16	0.56114 (19)	0.40453 (15)	0.20163 (17)	0.0446 (5)
C17	0.4322 (2)	0.39221 (15)	0.16311 (17)	0.0457 (5)
H17	0.3943	0.4302	0.1022	0.055*
C18	0.36099 (18)	0.32216 (14)	0.21721 (16)	0.0394 (4)
H18	0.2740	0.3142	0.1916	0.047*
Cl1	0.62411 (4)	0.20669 (4)	0.45204 (5)	0.05059 (17)
Cl2	0.65383 (6)	0.49418 (5)	0.13777 (6)	0.0727 (2)
N1	0.07592 (16)	0.19087 (13)	0.25047 (15)	0.0438 (4)
O1	0.35315 (14)	0.26245 (14)	0.58271 (14)	0.0638 (5)
O2	0.3688 (2)	0.00154 (15)	0.13564 (16)	0.0885 (7)
H1	0.006 (2)	0.1959 (17)	0.213 (2)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
C2	0.0286 (9)	0.0424 (10)	0.0386 (10)	−0.0049 (8)	−0.0028 (7)	0.0092 (8)
C3	0.0286 (9)	0.0395 (10)	0.0314 (9)	−0.0029 (7)	−0.0007 (7)	0.0038 (7)
C4	0.0304 (9)	0.0363 (9)	0.0297 (9)	−0.0005 (7)	−0.0065 (7)	0.0013 (7)
C5	0.0417 (10)	0.0348 (10)	0.0339 (9)	−0.0050 (8)	−0.0049 (8)	0.0011 (8)
C6	0.0483 (11)	0.0366 (10)	0.0351 (10)	−0.0091 (9)	−0.0095 (8)	0.0048 (8)
C7	0.0707 (15)	0.0496 (13)	0.0480 (12)	−0.0153 (11)	−0.0231 (11)	−0.0001 (10)
C8	0.0283 (10)	0.0693 (15)	0.0624 (13)	0.0005 (10)	−0.0016 (9)	0.0081 (11)
C9	0.0347 (10)	0.0472 (11)	0.0345 (9)	−0.0049 (8)	0.0019 (8)	0.0016 (8)
C10	0.0600 (13)	0.0636 (14)	0.0379 (11)	0.0095 (11)	0.0043 (9)	−0.0027 (10)
C11	0.0546 (12)	0.0396 (11)	0.0503 (12)	−0.0021 (9)	−0.0034 (9)	−0.0076 (9)
C12	0.0770 (17)	0.0506 (14)	0.0778 (17)	0.0214 (12)	−0.0178 (14)	−0.0106 (12)
C13	0.0282 (9)	0.0359 (9)	0.0295 (8)	0.0005 (7)	−0.0009 (7)	−0.0063 (7)
C14	0.0294 (9)	0.0392 (10)	0.0351 (9)	0.0036 (7)	−0.0025 (7)	−0.0043 (8)
C15	0.0290 (9)	0.0505 (12)	0.0469 (11)	−0.0040 (8)	0.0010 (8)	−0.0042 (9)
C16	0.0454 (11)	0.0459 (11)	0.0431 (11)	−0.0097 (9)	0.0076 (9)	−0.0009 (9)
C17	0.0492 (11)	0.0492 (12)	0.0377 (10)	−0.0045 (9)	−0.0051 (9)	0.0058 (9)
C18	0.0333 (9)	0.0474 (11)	0.0365 (10)	−0.0038 (8)	−0.0060 (8)	−0.0003 (8)
Cl1	0.0328 (3)	0.0580 (3)	0.0589 (3)	0.0034 (2)	−0.0119 (2)	0.0099 (2)
Cl2	0.0696 (4)	0.0779 (5)	0.0706 (4)	−0.0307 (3)	0.0044 (3)	0.0198 (3)
N1	0.0329 (9)	0.0529 (10)	0.0431 (9)	−0.0060 (7)	−0.0163 (7)	0.0043 (8)
O1	0.0408 (8)	0.0997 (13)	0.0485 (9)	0.0097 (8)	−0.0152 (7)	−0.0258 (9)
O2	0.1091 (16)	0.0922 (15)	0.0621 (11)	0.0329 (12)	−0.0095 (10)	−0.0350 (10)

C2—C3	1.365 (2)	C10—H10A	0.9600
C2—N1	1.375 (3)	C10—H10B	0.9600
C2—C8	1.502 (3)	C10—H10C	0.9600
C3—C9	1.469 (3)	C11—O2	1.220 (3)
C3—C4	1.524 (2)	C11—C12	1.492 (3)
C4—C5	1.524 (2)	C12—H12A	0.9600
C4—C13	1.533 (2)	C12—H12B	0.9600
C4—H4	0.9800	C12—H12C	0.9600
C5—C6	1.355 (3)	C13—C18	1.394 (3)
C5—C11	1.472 (3)	C13—C14	1.394 (2)
C6—N1	1.378 (3)	C14—C15	1.389 (3)
C6—C7	1.503 (3)	C14—Cl1	1.7444 (18)
C7—H7A	0.9600	C15—C16	1.366 (3)
C7—H7B	0.9600	C15—H15	0.9300
C7—H7C	0.9600	C16—C17	1.382 (3)
C8—H8A	0.9600	C16—Cl2	1.745 (2)
C8—H8B	0.9600	C17—C18	1.378 (3)
C8—H8C	0.9600	C17—H17	0.9300
C9—O1	1.228 (2)	C18—H18	0.9300
C9—C10	1.497 (3)	N1—H1	0.81 (2)
C3—C2—N1	119.17 (17)	H10A—C10—H10B	109.5
C3—C2—C8	128.40 (18)	C9—C10—H10C	109.5
N1—C2—C8	112.41 (16)	H10A—C10—H10C	109.5
C2—C3—C9	126.14 (17)	H10B—C10—H10C	109.5
C2—C3—C4	119.48 (16)	O2—C11—C5	122.6 (2)
C9—C3—C4	114.33 (15)	O2—C11—C12	118.9 (2)
C5—C4—C3	112.16 (14)	C5—C11—C12	118.43 (18)
C5—C4—C13	109.52 (14)	C11—C12—H12A	109.5
C3—C4—C13	110.04 (14)	C11—C12—H12B	109.5
C5—C4—H4	108.3	H12A—C12—H12B	109.5
C3—C4—H4	108.3	C11—C12—H12C	109.5
C13—C4—H4	108.3	H12A—C12—H12C	109.5
C6—C5—C11	120.76 (17)	H12B—C12—H12C	109.5
C6—C5—C4	119.86 (17)	C18—C13—C14	115.67 (16)
C11—C5—C4	119.35 (16)	C18—C13—C4	119.28 (15)
C5—C6—N1	118.96 (17)	C14—C13—C4	125.05 (16)
C5—C6—C7	126.61 (19)	C15—C14—C13	122.33 (17)
N1—C6—C7	114.35 (18)	C15—C14—Cl1	116.38 (13)
C6—C7—H7A	109.5	C13—C14—Cl1	121.28 (14)
C6—C7—H7B	109.5	C16—C15—C14	119.20 (17)
H7A—C7—H7B	109.5	C16—C15—H15	120.4
C6—C7—H7C	109.5	C14—C15—H15	120.4
H7A—C7—H7C	109.5	C15—C16—C17	121.10 (18)
H7B—C7—H7C	109.5	C15—C16—Cl2	119.04 (15)
C2—C8—H8A	109.5	C17—C16—Cl2	119.85 (16)
C2—C8—H8B	109.5	C18—C17—C16	118.35 (18)
H8A—C8—H8B	109.5	C18—C17—H17	120.8
C2—C8—H8C	109.5	C16—C17—H17	120.8
H8A—C8—H8C	109.5	C17—C18—C13	123.34 (17)
H8B—C8—H8C	109.5	C17—C18—H18	118.3
O1—C9—C3	118.17 (17)	C13—C18—H18	118.3
O1—C9—C10	117.81 (17)	C2—N1—C6	124.61 (16)
C3—C9—C10	123.98 (17)	C2—N1—H1	118.2 (16)
C9—C10—H10A	109.5	C6—N1—H1	116.5 (16)
C9—C10—H10B	109.5
N1—C2—C3—C9	−177.66 (17)	C4—C5—C11—C12	34.8 (3)
C8—C2—C3—C9	0.5 (3)	C5—C4—C13—C18	62.3 (2)
N1—C2—C3—C4	4.8 (3)	C3—C4—C13—C18	−61.4 (2)
C8—C2—C3—C4	−177.01 (18)	C5—C4—C13—C14	−116.97 (18)
C2—C3—C4—C5	−22.3 (2)	C3—C4—C13—C14	119.30 (18)
C9—C3—C4—C5	159.92 (15)	C18—C13—C14—C15	1.2 (3)
C2—C3—C4—C13	99.89 (18)	C4—C13—C14—C15	−179.54 (16)
C9—C3—C4—C13	−77.89 (18)	C18—C13—C14—Cl1	−177.96 (13)
C3—C4—C5—C6	24.6 (2)	C4—C13—C14—Cl1	1.3 (2)
C13—C4—C5—C6	−97.9 (2)	C13—C14—C15—C16	−1.4 (3)
C3—C4—C5—C11	−157.55 (16)	Cl1—C14—C15—C16	177.78 (15)
C13—C4—C5—C11	80.0 (2)	C14—C15—C16—C17	0.6 (3)
C11—C5—C6—N1	173.01 (18)	C14—C15—C16—Cl2	179.48 (15)
C4—C5—C6—N1	−9.1 (3)	C15—C16—C17—C18	0.2 (3)
C11—C5—C6—C7	−3.6 (3)	Cl2—C16—C17—C18	−178.61 (16)
C4—C5—C6—C7	174.23 (18)	C16—C17—C18—C13	−0.4 (3)
C2—C3—C9—O1	172.37 (19)	C14—C13—C18—C17	−0.3 (3)
C4—C3—C9—O1	−10.0 (3)	C4—C13—C18—C17	−179.59 (18)
C2—C3—C9—C10	−10.0 (3)	C3—C2—N1—C6	13.8 (3)
C4—C3—C9—C10	167.64 (18)	C8—C2—N1—C6	−164.67 (18)
C6—C5—C11—O2	31.2 (3)	C5—C6—N1—C2	−11.5 (3)
C4—C5—C11—O2	−146.6 (2)	C7—C6—N1—C2	165.50 (18)
C6—C5—C11—C12	−147.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.81 (2)	2.16 (2)	2.951 (2)	163 (2)
C8—H8B···O2ii	0.96	2.56	3.397 (3)	147
C10—H10C···O2ii	0.96	2.43	3.341 (3)	158
C4—H4···Cl1	0.98	2.65	3.190 (2)	115
C17—H17···Cl2iii	0.93 (1)	2.92 (1)	3.796 (2)	158.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.81 (2)	2.16 (2)	2.951 (2)	163 (2)
C8—H8B⋯O2ii	0.96	2.56	3.397 (3)	147
C10—H10C⋯O2ii	0.96	2.43	3.341 (3)	158
C17—H17⋯Cl2iii	0.93 (1)	2.92 (1)	3.796 (2)	158 (1)

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