1,1′-[4-(5-Bromo-2-fur­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-di­yl]diethanone

In the title compound, C₁₅H₁₆BrNO₃, the central 1,4-dihydro­pyridine (1,4-DHP) ring adopts a flattened boat conformation with the furyl group in a pseudoaxial orientation. The acetyl substituents of the 1,4-DHP ring at positions 3 and 5 have different (cis/trans) configurations with respect to the double bonds in the 1,4-DHP ring. The mol­ecules form chains, parallel to the b axis, via N—H...O inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.031
• wR factor = 0.111
• Data-to-parameter ratio = 19.9

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97.

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

Crystal data

C15H16BrNO3	F(000) = 688
Mr = 338.20	Dx = 1.514 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15729 reflections
a = 8.1910 (1) Å	θ = 3.0–28.9°
b = 15.1488 (2) Å	µ = 2.78 mm^−1
c = 12.5623 (2) Å	T = 295 K
β = 107.885 (2)°	Prism, yellow
V = 1483.45 (4) Å^3	0.6 × 0.5 × 0.4 mm
Z = 4

Data collection

Oxford Diffraction Gemini R CCD diffractometer	3685 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with F^2 > 2σ(F^2)
Graphite monochromator	Rint = 0.020
Detector resolution: 10.4340 pixels mm^-1	θmax = 29.0°, θmin = 2.9°
Rotation method data acquisition using ω and φ scans	h = −10→11
Absorption correction: analytical (Clark & Reid, 1995)	k = −20→18
Tmin = 0.202, Tmax = 0.329	l = −16→16
32417 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 1.3458P] where P = (Fo^2 + 2Fc^2)/3
3685 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Special details

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction Limited, 2006) IR (KBr): 3252 (N—H), 3098 (=C—H), 1651 (C=O), 1477 cm^-1; ¹H NMR (DMSO-d₆) δ: 2.27 (s, 12H); 5.11 (s, 1H, H-4); 5.92 (d, 1H, H-4', J = 3.0 Hz); 6.34 (d, 1H, H-3', J = 3.1 Hz); 9.08 (s, 1H, NH); ¹³C NMR (DMSO-d₆) δ: 19.06, 29.85, 33.24, 107.51, 108.46, 112.11, 118.87, 145.93, 160.54, 195.80; EIMS, m/z: (M⁺, 337). Anal. Calcd for C₁₅H₁₆BrNO₃: C, 53.27; H, 4.77; N, 4.14; Found: C, 53.05; H, 4.61; N, 3.99.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.3943 (3)	0.81059 (15)	0.16738 (19)	0.0279 (5)
C3	0.4221 (3)	0.85634 (14)	0.26428 (17)	0.0250 (4)
C4	0.3223 (3)	0.94131 (14)	0.25935 (17)	0.0244 (4)
H4	0.3875	0.9797	0.3204	0.029*
C5	0.2990 (3)	0.98922 (15)	0.14885 (19)	0.0370 (5)
C6	0.2684 (3)	0.93835 (16)	0.05605 (18)	0.0296 (5)
C21	0.4591 (3)	0.71995 (16)	0.1524 (2)	0.0384 (6)
H21A	0.4023	0.6994	0.0779	0.058*
H21B	0.4359	0.6802	0.2055	0.058*
H21C	0.5805	0.7224	0.1643	0.058*
C31	0.5237 (3)	0.82049 (15)	0.37223 (18)	0.0293 (5)
C32	0.5069 (4)	0.8613 (2)	0.4774 (2)	0.0455 (6)
H32A	0.5522	0.8216	0.5390	0.068*
H32B	0.3881	0.8726	0.4684	0.068*
H32C	0.5696	0.9158	0.4919	0.068*
C41	0.1532 (3)	0.92071 (15)	0.27679 (18)	0.0275 (5)
C42	−0.0762 (3)	0.95305 (17)	0.3222 (2)	0.0346 (5)
C43	−0.0916 (3)	0.86792 (18)	0.2946 (2)	0.0414 (6)
H43	−0.1810	0.8302	0.2950	0.050*
C44	0.0585 (3)	0.84666 (16)	0.2645 (2)	0.0373 (5)
H44	0.0855	0.7920	0.2408	0.045*
C51	0.3090 (3)	1.08575 (16)	0.1544 (2)	0.0365 (5)
C52	0.2931 (7)	1.1423 (2)	0.0530 (3)	0.0467 (13)
H52A	0.3255	1.2018	0.0762	0.070*
H52B	0.1765	1.1414	0.0050	0.070*
H52C	0.3670	1.1197	0.0131	0.070*
C61	0.2075 (4)	0.96478 (19)	−0.0654 (2)	0.0482 (7)
H61A	0.1481	0.9161	−0.1096	0.072*
H61B	0.3043	0.9808	−0.0891	0.072*
H61C	0.1312	1.0143	−0.0748	0.072*
N1	0.2964 (3)	0.84896 (13)	0.06940 (16)	0.0328 (4)
H1	0.2501	0.8151	0.0132	0.039*
O31	0.6218 (2)	0.75737 (12)	0.37954 (14)	0.0407 (4)
O41	0.0706 (2)	0.98865 (11)	0.31272 (14)	0.0311 (4)
O51	0.3372 (3)	1.12277 (12)	0.24448 (17)	0.0548 (6)
Br41	−0.21978 (4)	1.02936 (2)	0.36731 (3)	0.05706 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0281 (10)	0.0252 (11)	0.0289 (11)	0.0006 (9)	0.0067 (9)	0.0022 (9)
C3	0.0238 (10)	0.0255 (10)	0.0245 (10)	0.0007 (8)	0.0057 (8)	0.0015 (8)
C4	0.0268 (10)	0.0236 (10)	0.0217 (10)	−0.0008 (8)	0.0059 (8)	−0.0022 (8)
C5	0.0269 (11)	0.0243 (11)	0.0287 (11)	0.0000 (9)	0.0067 (9)	0.0028 (9)
C6	0.0310 (11)	0.0294 (11)	0.0253 (11)	0.0009 (9)	0.0040 (9)	0.0026 (9)
C21	0.0453 (14)	0.0294 (12)	0.0378 (13)	0.0070 (11)	0.0089 (11)	−0.0026 (10)
C31	0.0298 (11)	0.0293 (11)	0.0279 (11)	−0.0023 (9)	0.0077 (9)	0.0039 (9)
C32	0.0580 (17)	0.0512 (16)	0.0248 (12)	0.0109 (14)	0.0092 (11)	0.0049 (11)
C41	0.0295 (11)	0.0265 (11)	0.0268 (10)	0.0037 (9)	0.0091 (9)	0.0019 (9)
C42	0.0318 (12)	0.0391 (13)	0.0372 (13)	0.0016 (10)	0.0167 (10)	0.0030 (10)
C43	0.0371 (13)	0.0379 (14)	0.0542 (16)	−0.0059 (11)	0.0212 (12)	0.0035 (12)
C44	0.0394 (13)	0.0276 (12)	0.0489 (15)	−0.0020 (10)	0.0193 (11)	−0.0005 (11)
C51	0.0458 (14)	0.0261 (12)	0.0401 (13)	0.0009 (10)	0.0166 (11)	0.0022 (10)
C52	0.0605 (4)	0.0280 (15)	0.0543 (19)	−0.006 (2)	0.033 (2)	0.0092 (14)
C61	0.069 (2)	0.0419 (15)	0.0259 (13)	0.0074 (13)	0.0028 (12)	0.0044 (11)
N1	0.0406 (11)	0.0256 (10)	0.0251 (9)	0.0025 (8)	−0.0005 (8)	−0.0039 (8)
O31	0.0451 (10)	0.0392 (10)	0.0340 (9)	0.0146 (8)	0.0066 (8)	0.0100 (8)
O41	0.0315 (8)	0.0296 (8)	0.0360 (9)	0.0002 (7)	0.0158 (7)	−0.0013 (7)
O51	0.0927 (16)	0.0277 (9)	0.0478 (11)	−0.0028 (10)	0.0273 (11)	−0.0069 (8)
Br41	0.0510 (2)	0.0521 (2)	0.0836 (3)	−0.00084 (13)	0.04360 (18)	−0.01053 (15)

Geometric parameters (Å, º)

C2—C3	1.358 (3)	C32—H32C	0.9600
C2—N1	1.375 (3)	C41—C44	1.346 (3)
C2—C21	1.505 (3)	C41—O41	1.381 (3)
C3—C31	1.461 (3)	C42—O41	1.356 (3)
C3—C4	1.516 (3)	C42—C43	1.331 (4)
C4—C41	1.500 (3)	C42—Br41	1.857 (3)
C4—C5	1.526 (3)	C43—C44	1.430 (4)
C4—H4	0.9800	C43—H43	0.9300
C5—C6	1.355 (3)	C44—H44	0.9300
C5—C51	1.465 (3)	C51—O51	1.220 (3)
C6—N1	1.375 (3)	C51—C52	1.507 (4)
C6—C61	1.506 (3)	C52—H52A	0.9600
C21—H21A	0.9600	C52—H52B	0.9600
C21—H21B	0.9600	C52—H52C	0.9600
C21—H21C	0.9600	C61—H61A	0.9600
C31—O31	1.234 (3)	C61—H61B	0.9600
C31—C32	1.503 (3)	C61—H61C	0.9600
C32—H32A	0.9600	N1—H1	0.8600
C32—H32B	0.9600
C3—C2—N1	118.6 (2)	H32B—C32—H32C	109.5
C3—C2—C21	127.5 (2)	C44—C41—O41	109.6 (2)
N1—C2—C21	113.9 (2)	C44—C41—C4	133.0 (2)
C2—C3—C31	122.2 (2)	O41—C41—C4	117.35 (19)
C2—C3—C4	117.19 (18)	O41—C42—C43	112.2 (2)
C31—C3—C4	120.00 (19)	O41—C42—Br41	116.15 (18)
C41—C4—C3	109.13 (18)	C43—C42—Br41	131.6 (2)
C41—C4—C5	111.63 (18)	C42—C43—C44	105.5 (2)
C3—C4—C5	110.88 (18)	C42—C43—H43	127.3
C41—C4—H4	108.4	C44—C43—H43	127.3
C3—C4—H4	108.4	C41—C44—C43	107.1 (2)
C5—C4—H4	108.4	C41—C44—H44	126.5
C6—C5—C51	127.0 (2)	C43—C44—H44	126.5
C6—C5—C4	116.8 (2)	O51—C51—C5	119.7 (2)
C51—C5—C4	116.2 (2)	O51—C51—C52	117.7 (2)
C5—C6—N1	118.4 (2)	C5—C51—C52	122.5 (2)
C5—C6—C61	129.5 (2)	C51—C52—H52A	109.5
N1—C6—C61	112.1 (2)	C51—C52—H52B	109.5
C2—C21—H21A	109.5	H52A—C52—H52B	109.5
C2—C21—H21B	109.5	C51—C52—H52C	109.5
H21A—C21—H21B	109.5	H52A—C52—H52C	109.5
C2—C21—H21C	109.5	H52B—C52—H52C	109.5
H21A—C21—H21C	109.5	C6—C61—H61A	109.5
H21B—C21—H21C	109.5	C6—C61—H61B	109.5
O31—C31—C3	122.0 (2)	H61A—C61—H61B	109.5
O31—C31—C32	119.1 (2)	C6—C61—H61C	109.5
C3—C31—C32	118.9 (2)	H61A—C61—H61C	109.5
C31—C32—H32A	109.5	H61B—C61—H61C	109.5
C31—C32—H32B	109.5	C6—N1—C2	123.72 (19)
H32A—C32—H32B	109.5	C6—N1—H1	118.1
C31—C32—H32C	109.5	C2—N1—H1	118.1
H32A—C32—H32C	109.5	C42—O41—C41	105.58 (18)
N1—C2—C3—C31	179.7 (2)	C5—C4—C41—C44	101.4 (3)
C21—C2—C3—C31	−0.4 (4)	C3—C4—C41—O41	158.51 (18)
N1—C2—C3—C4	8.4 (3)	C5—C4—C41—O41	−78.6 (2)
C21—C2—C3—C4	−171.7 (2)	O41—C42—C43—C44	−0.2 (3)
C2—C3—C4—C41	87.7 (2)	Br41—C42—C43—C44	178.5 (2)
C31—C3—C4—C41	−83.8 (2)	O41—C41—C44—C43	−0.4 (3)
C2—C3—C4—C5	−35.6 (3)	C4—C41—C44—C43	179.7 (2)
C31—C3—C4—C5	152.8 (2)	C42—C43—C44—C41	0.3 (3)
C41—C4—C5—C6	−83.5 (3)	C6—C5—C51—O51	179.8 (3)
C3—C4—C5—C6	38.4 (3)	C4—C5—C51—O51	1.0 (4)
C41—C4—C5—C51	95.4 (2)	C6—C5—C51—C52	−2.8 (5)
C3—C4—C5—C51	−142.7 (2)	C4—C5—C51—C52	178.4 (3)
C51—C5—C6—N1	167.6 (2)	C5—C6—N1—C2	−17.8 (4)
C4—C5—C6—N1	−13.6 (3)	C61—C6—N1—C2	161.6 (2)
C51—C5—C6—C61	−11.7 (4)	C3—C2—N1—C6	20.8 (4)
C4—C5—C6—C61	167.1 (3)	C21—C2—N1—C6	−159.1 (2)
C2—C3—C31—O31	17.3 (3)	C43—C42—O41—C41	−0.1 (3)
C4—C3—C31—O31	−171.6 (2)	Br41—C42—O41—C41	−179.00 (15)
C2—C3—C31—C32	−162.2 (2)	C44—C41—O41—C42	0.3 (3)
C4—C3—C31—C32	8.9 (3)	C4—C41—O41—C42	−179.76 (19)
C3—C4—C41—C44	−21.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O31^i	0.86	2.01	2.869 (2)	175

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.