3,5-Diacetyl-2,6-dimethyl-4-(5-nitro-2-fur­yl)-1,4-dihydro­pyridine

In the mol­ecule of the title compound, C₁₅H₁₆N₂O₅, the 5-nitro substituent on the furan ring is rotated from coplanarity with the ring by only 2.1 (2)°. The central 1,4-dihydro­pyridine (1,4-DHP) ring adopts a flattened boat conformation with the 4-furyl group in a pseudo-axial orientation. Both acetyl substituents of the 1,4-DHP ring at positions 3 and 5 have a synperiplanar conformation. In the crystal structure, intra­molecular C—H...O and inter­molecular N—H...O and C—H...O hydrogen bonds lead to the formation of infinite sheets of mol­ecules; they seem to be effective in the stabilization of the structure.

Key indicators

• Single-crystal X-ray study
• T = 301 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.149
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.00 Sigma
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N41
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  O43     ..       2.92 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); 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.

3,5-diacetyl-2,6-dimethyl-4-(5-nitro-2-furyl)-1,4-dihydropyridine

Crystal data

C15H16N2O5	F(000) = 640
Mr = 304.30	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8320 reflections
a = 8.7056 (7) Å	θ = 2.2–31.4°
b = 12.2393 (9) Å	µ = 0.10 mm^−1
c = 13.829 (1) Å	T = 301 K
β = 93.608 (7)°	Plate, yellow
V = 1470.6 (2) Å^3	0.50 × 0.30 × 0.30 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	2378 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.4°, θmin = 4.2°
ω and φ scans	h = −10→10
8961 measured reflections	k = −15→15
2981 independent reflections	l = −9→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0879P)^2 + 0.2265P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.003
2981 reflections	Δρmax = 0.24 e Å^−3
204 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (2)

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

	x	y	z	Uiso*/Ueq
N1	0.63135 (17)	0.97750 (11)	0.16414 (10)	0.0394 (4)
H1	0.6384	1.0284	0.2070	0.047*
N41	0.9808 (2)	0.48027 (15)	0.12875 (14)	0.0620 (5)
C2	0.55200 (18)	0.88509 (12)	0.18539 (11)	0.0345 (4)
C3	0.56056 (17)	0.79614 (12)	0.12774 (10)	0.0303 (3)
C4	0.67584 (17)	0.79579 (12)	0.04902 (11)	0.0313 (4)
H4	0.6308	0.7556	−0.0071	0.038*
C5	0.71488 (18)	0.91069 (12)	0.01682 (11)	0.0336 (4)
C6	0.70074 (19)	0.99448 (13)	0.07874 (11)	0.0363 (4)
C21	0.4556 (2)	0.89752 (15)	0.27033 (14)	0.0501 (5)
H21A	0.4277	0.9729	0.2771	0.075*
H21B	0.5131	0.8736	0.3280	0.075*
H21C	0.3642	0.8541	0.2604	0.075*
C31	0.46860 (18)	0.69858 (12)	0.14135 (11)	0.0337 (4)
C32	0.4338 (2)	0.62392 (15)	0.05751 (14)	0.0470 (5)
H32A	0.3551	0.5732	0.0732	0.071*
H32B	0.5252	0.5846	0.0435	0.071*
H32C	0.3988	0.6660	0.0018	0.071*
C41	0.82001 (18)	0.73863 (13)	0.08548 (11)	0.0343 (4)
C42	0.9580 (2)	0.77283 (15)	0.12357 (14)	0.0460 (4)
H42	0.9897	0.8450	0.1319	0.055*
C43	1.0450 (2)	0.67896 (16)	0.14836 (15)	0.0511 (5)
H43	1.1449	0.6764	0.1764	0.061*
C44	0.9546 (2)	0.59436 (15)	0.12325 (13)	0.0442 (4)
C51	0.7779 (2)	0.92406 (14)	−0.07884 (12)	0.0428 (4)
C52	0.7787 (3)	0.82811 (18)	−0.14525 (14)	0.0656 (6)
H52A	0.8268	0.8481	−0.2033	0.098*
H52B	0.6747	0.8052	−0.1615	0.098*
H52C	0.8349	0.7693	−0.1138	0.098*
C61	0.7507 (3)	1.11024 (14)	0.06494 (15)	0.0526 (5)
H61A	0.7151	1.1548	0.1161	0.079*
H61B	0.7080	1.1368	0.0037	0.079*
H61C	0.8610	1.1133	0.0661	0.079*
O31	0.41691 (15)	0.67584 (10)	0.21959 (9)	0.0464 (4)
O41	0.81471 (13)	0.62628 (9)	0.08497 (8)	0.0409 (3)
O42	0.8784 (2)	0.41778 (14)	0.10181 (16)	0.0955 (7)
O43	1.1090 (2)	0.45193 (16)	0.16101 (16)	0.0973 (7)
O51	0.8286 (2)	1.01024 (13)	−0.10667 (11)	0.0754 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0514 (9)	0.0293 (7)	0.0383 (7)	−0.0060 (6)	0.0093 (6)	−0.0059 (5)
N41	0.0662 (12)	0.0458 (10)	0.0732 (12)	0.0181 (9)	−0.0023 (9)	0.0020 (8)
C2	0.0385 (8)	0.0306 (8)	0.0348 (8)	0.0004 (6)	0.0052 (6)	0.0002 (6)
C3	0.0310 (8)	0.0283 (7)	0.0318 (7)	0.0006 (6)	0.0047 (6)	0.0015 (6)
C4	0.0355 (8)	0.0292 (8)	0.0294 (7)	−0.0007 (6)	0.0048 (6)	−0.0008 (6)
C5	0.0359 (8)	0.0308 (8)	0.0345 (8)	−0.0026 (6)	0.0042 (6)	0.0041 (6)
C6	0.0383 (9)	0.0310 (8)	0.0395 (8)	−0.0016 (6)	0.0022 (7)	0.0045 (6)
C21	0.0649 (12)	0.0400 (9)	0.0480 (10)	0.0005 (9)	0.0243 (9)	−0.0056 (8)
C31	0.0319 (8)	0.0294 (8)	0.0400 (8)	0.0028 (6)	0.0039 (6)	0.0025 (6)
C32	0.0509 (11)	0.0384 (9)	0.0521 (10)	−0.0112 (8)	0.0045 (8)	−0.0048 (8)
C41	0.0387 (9)	0.0295 (8)	0.0358 (8)	0.0014 (6)	0.0112 (6)	0.0008 (6)
C42	0.0363 (9)	0.0418 (10)	0.0606 (11)	−0.0039 (7)	0.0079 (8)	0.0031 (8)
C43	0.0332 (9)	0.0580 (12)	0.0627 (12)	0.0023 (8)	0.0074 (8)	0.0065 (9)
C44	0.0415 (9)	0.0416 (9)	0.0497 (10)	0.0108 (8)	0.0058 (7)	0.0032 (7)
C51	0.0455 (10)	0.0435 (10)	0.0402 (9)	−0.0047 (8)	0.0088 (7)	0.0062 (7)
C52	0.0972 (18)	0.0623 (13)	0.0402 (10)	−0.0127 (12)	0.0277 (11)	−0.0042 (9)
C61	0.0672 (13)	0.0318 (9)	0.0596 (11)	−0.0082 (9)	0.0102 (10)	0.0022 (8)
O31	0.0540 (8)	0.0385 (7)	0.0483 (7)	−0.0073 (5)	0.0162 (6)	0.0066 (5)
O41	0.0424 (7)	0.0313 (6)	0.0488 (7)	0.0051 (5)	0.0007 (5)	−0.0012 (5)
O42	0.1018 (14)	0.0420 (9)	0.1373 (18)	0.0103 (9)	−0.0351 (13)	−0.0081 (10)
O43	0.0749 (12)	0.0693 (11)	0.1444 (18)	0.0336 (10)	−0.0177 (12)	0.0128 (11)
O51	0.1115 (14)	0.0576 (9)	0.0609 (9)	−0.0263 (9)	0.0353 (9)	0.0077 (7)

Geometric parameters (Å, º)

N1—C2	1.367 (2)	C51—O51	1.215 (2)
N1—C6	1.376 (2)	C51—C52	1.491 (3)
N1—H1	0.8600	C42—C43	1.407 (3)
N41—O42	1.215 (3)	C42—H42	0.9300
N41—O43	1.226 (2)	C21—H21A	0.9600
N41—C44	1.416 (3)	C21—H21B	0.9600
C4—C41	1.496 (2)	C21—H21C	0.9600
C4—C5	1.520 (2)	C44—C43	1.334 (3)
C4—C3	1.526 (2)	C44—O41	1.354 (2)
C4—H4	0.9800	C43—H43	0.9300
C3—C2	1.354 (2)	C32—H32A	0.9600
C3—C31	1.456 (2)	C32—H32B	0.9600
C41—C42	1.347 (2)	C32—H32C	0.9600
C41—O41	1.3758 (19)	C61—H61A	0.9600
C31—O31	1.2297 (19)	C61—H61B	0.9600
C31—C32	1.492 (2)	C61—H61C	0.9600
C5—C6	1.347 (2)	C52—H52A	0.9600
C5—C51	1.473 (2)	C52—H52B	0.9600
C2—C21	1.494 (2)	C52—H52C	0.9600
C6—C61	1.498 (2)
C2—N1—C6	124.38 (13)	C41—C42—H42	126.4
C2—N1—H1	117.8	C43—C42—H42	126.4
C6—N1—H1	117.8	C2—C21—H21A	109.5
O42—N41—O43	124.6 (2)	C2—C21—H21B	109.5
O42—N41—C44	119.43 (18)	H21A—C21—H21B	109.5
O43—N41—C44	116.0 (2)	C2—C21—H21C	109.5
C41—C4—C5	109.45 (13)	H21A—C21—H21C	109.5
C41—C4—C3	109.64 (12)	H21B—C21—H21C	109.5
C5—C4—C3	112.05 (12)	C43—C44—O41	112.29 (16)
C41—C4—H4	108.5	C43—C44—N41	131.38 (18)
C5—C4—H4	108.5	O41—C44—N41	116.32 (17)
C3—C4—H4	108.5	C44—C43—C42	105.69 (16)
C2—C3—C31	122.14 (13)	C44—C43—H43	127.2
C2—C3—C4	119.02 (13)	C42—C43—H43	127.2
C31—C3—C4	118.77 (13)	C31—C32—H32A	109.5
C42—C41—O41	109.95 (14)	C31—C32—H32B	109.5
C42—C41—C4	133.99 (15)	H32A—C32—H32B	109.5
O41—C41—C4	116.00 (13)	C31—C32—H32C	109.5
O31—C31—C3	122.27 (14)	H32A—C32—H32C	109.5
O31—C31—C32	118.52 (14)	H32B—C32—H32C	109.5
C3—C31—C32	119.21 (14)	C6—C61—H61A	109.5
C6—C5—C51	122.72 (14)	C6—C61—H61B	109.5
C6—C5—C4	119.16 (14)	H61A—C61—H61B	109.5
C51—C5—C4	117.95 (14)	C6—C61—H61C	109.5
C3—C2—N1	119.43 (14)	H61A—C61—H61C	109.5
C3—C2—C21	126.83 (15)	H61B—C61—H61C	109.5
N1—C2—C21	113.65 (14)	C51—C52—H52A	109.5
C5—C6—N1	119.56 (14)	C51—C52—H52B	109.5
C5—C6—C61	126.91 (15)	H52A—C52—H52B	109.5
N1—C6—C61	113.51 (14)	C51—C52—H52C	109.5
O51—C51—C5	122.97 (17)	H52A—C52—H52C	109.5
O51—C51—C52	118.21 (16)	H52B—C52—H52C	109.5
C5—C51—C52	118.81 (15)	C44—O41—C41	104.91 (13)
C41—C42—C43	107.15 (16)
C41—C4—C3—C2	96.31 (17)	C4—C5—C6—N1	−9.1 (2)
C5—C4—C3—C2	−25.43 (19)	C51—C5—C6—C61	−3.0 (3)
C41—C4—C3—C31	−80.77 (17)	C4—C5—C6—C61	172.28 (16)
C5—C4—C3—C31	157.49 (13)	C2—N1—C6—C5	−11.1 (3)
C5—C4—C41—C42	25.1 (2)	C2—N1—C6—C61	167.75 (16)
C3—C4—C41—C42	−98.2 (2)	C6—C5—C51—O51	3.8 (3)
C5—C4—C41—O41	−157.90 (12)	C4—C5—C51—O51	−171.54 (18)
C3—C4—C41—O41	78.81 (16)	C6—C5—C51—C52	−175.66 (18)
C2—C3—C31—O31	−23.5 (2)	C4—C5—C51—C52	9.0 (2)
C4—C3—C31—O31	153.53 (15)	O41—C41—C42—C43	0.1 (2)
C2—C3—C31—C32	155.79 (16)	C4—C41—C42—C43	177.28 (16)
C4—C3—C31—C32	−27.2 (2)	O42—N41—C44—C43	179.2 (2)
C41—C4—C5—C6	−96.12 (17)	O43—N41—C44—C43	−1.0 (3)
C3—C4—C5—C6	25.7 (2)	O42—N41—C44—O41	−1.7 (3)
C41—C4—C5—C51	79.38 (17)	O43—N41—C44—O41	178.08 (18)
C3—C4—C5—C51	−158.77 (14)	O41—C44—C43—C42	−0.7 (2)
C31—C3—C2—N1	−174.56 (14)	N41—C44—C43—C42	178.4 (2)
C4—C3—C2—N1	8.5 (2)	C41—C42—C43—C44	0.3 (2)
C31—C3—C2—C21	1.8 (3)	C43—C44—O41—C41	0.7 (2)
C4—C3—C2—C21	−175.17 (16)	N41—C44—O41—C41	−178.49 (15)
C6—N1—C2—C3	11.3 (2)	C42—C41—O41—C44	−0.51 (18)
C6—N1—C2—C21	−165.50 (16)	C4—C41—O41—C44	−178.23 (13)
C51—C5—C6—N1	175.65 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O31^i	0.86	2.14	2.9562 (17)	158
N1—H1···O43^ii	0.86	2.92	3.219 (3)	103
C42—H42···O51^iii	0.93	2.42	3.257 (2)	151
C43—H43···O31^iv	0.93	2.41	3.324 (2)	170
C21—H21C···O31	0.96	2.31	2.817 (2)	113
C32—H32B···O41	0.96	2.60	3.314 (2)	131
C61—H61B···O51	0.96	2.46	2.792 (3)	100

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+2, −y+2, −z; (iv) x+1, y, z.