Acetonyl methyl 1,4-dihydro-2,6-dimethyl-4-(2-nitro­phen­yl)pyridine-3,5-dicarboxyl­ate

In the title compound, C₁₉H₂₀N₂O₇, the C atom in the 4-position of the dihydro­pyridine ring is displaced out of the plane by 0.0461 (2) Å. The dihydro­pyridine ring plane is almost perpendicular to the benzene ring, with a dihedral angle of 88.9 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.118
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.57 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Methyl 2-oxopropyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate

Crystal data

C19H20N2O7	F(000) = 1632
Mr = 388.37	Dx = 1.393 Mg m^−3
Monoclinic, C2/c	Melting point: 423 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 26.462 (15) Å	Cell parameters from 2469 reflections
b = 9.566 (6) Å	θ = 2.3–25.5°
c = 16.159 (9) Å	µ = 0.11 mm^−1
β = 115.155 (6)°	T = 293 K
V = 3703 (4) Å^3	Block, yellow
Z = 8	0.36 × 0.22 × 0.16 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	3273 independent reflections
Radiation source: fine-focus sealed tube	2456 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −31→31
Tmin = 0.972, Tmax = 0.983	k = −11→7
9700 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 2.0965P] where P = (Fo^2 + 2Fc^2)/3
3272 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.11482 (8)	0.5093 (2)	0.57173 (12)	0.0876 (6)
O2	0.19705 (7)	0.5448 (2)	0.57994 (10)	0.0732 (5)
O3	0.26500 (6)	0.49363 (16)	0.48436 (9)	0.0587 (4)
O4	0.30364 (6)	0.49966 (16)	0.38657 (10)	0.0600 (4)
O5	0.06544 (7)	0.92405 (18)	0.35051 (12)	0.0752 (5)
O6	0.10873 (5)	0.77002 (14)	0.46104 (9)	0.0481 (3)
O7	−0.00870 (9)	0.8085 (3)	0.51165 (17)	0.1234 (9)
N1	0.14856 (9)	0.50940 (19)	0.53820 (12)	0.0563 (5)
N2	0.18051 (7)	0.80593 (18)	0.24309 (10)	0.0490 (4)
H2A	0.1787	0.8417	0.1931	0.059*
C1	0.12823 (8)	0.4617 (2)	0.44266 (12)	0.0427 (4)
C2	0.09312 (8)	0.3473 (2)	0.42076 (15)	0.0523 (5)
H2	0.0835	0.3076	0.4646	0.063*
C3	0.07251 (9)	0.2926 (2)	0.33434 (17)	0.0586 (6)
H3	0.0494	0.2144	0.3194	0.070*
C4	0.08627 (9)	0.3543 (2)	0.26987 (15)	0.0555 (5)
H4	0.0723	0.3181	0.2109	0.067*
C5	0.12092 (8)	0.4703 (2)	0.29245 (12)	0.0445 (5)
H5	0.1294	0.5110	0.2476	0.053*
C6	0.14340 (7)	0.52769 (18)	0.37955 (11)	0.0361 (4)
C7	0.17823 (7)	0.66175 (18)	0.39509 (11)	0.0362 (4)
H7	0.1961	0.6816	0.4608	0.043*
C8	0.22375 (7)	0.64259 (19)	0.36151 (11)	0.0377 (4)
C9	0.26791 (8)	0.5414 (2)	0.40914 (12)	0.0420 (4)
C10	0.30471 (9)	0.3885 (2)	0.53532 (16)	0.0663 (6)
H10A	0.2979	0.3048	0.4994	0.100*
H10B	0.3010	0.3687	0.5908	0.100*
H10C	0.3418	0.4215	0.5500	0.100*
C11	0.22292 (8)	0.7133 (2)	0.28864 (12)	0.0429 (4)
C12	0.26515 (10)	0.7052 (3)	0.24955 (15)	0.0606 (6)
H12A	0.3019	0.7170	0.2977	0.091*
H12B	0.2579	0.7776	0.2048	0.091*
H12C	0.2626	0.6157	0.2212	0.091*
C13	0.14078 (8)	0.84514 (19)	0.27223 (12)	0.0422 (4)
C14	0.10362 (10)	0.9601 (2)	0.21564 (15)	0.0602 (6)
H14A	0.0668	0.9482	0.2124	0.090*
H14B	0.1019	0.9570	0.1551	0.090*
H14C	0.1184	1.0487	0.2431	0.090*
C15	0.13954 (7)	0.78333 (18)	0.34647 (12)	0.0380 (4)
C16	0.10062 (8)	0.8350 (2)	0.38199 (13)	0.0459 (5)
C17	0.07628 (9)	0.8229 (2)	0.50625 (14)	0.0573 (6)
H17A	0.0741	0.9238	0.4997	0.069*
H17B	0.0959	0.8023	0.5710	0.069*
C18	0.01840 (10)	0.7669 (3)	0.47277 (17)	0.0641 (6)
C19	−0.00387 (10)	0.6658 (3)	0.39615 (18)	0.0770 (7)
H19A	−0.0406	0.6369	0.3870	0.116*
H19B	0.0202	0.5857	0.4104	0.116*
H19C	−0.0056	0.7093	0.3414	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1064 (14)	0.1152 (16)	0.0734 (11)	−0.0069 (11)	0.0692 (11)	0.0033 (10)
O2	0.0719 (11)	0.1015 (14)	0.0428 (8)	−0.0043 (10)	0.0210 (8)	0.0023 (8)
O3	0.0539 (8)	0.0683 (10)	0.0588 (9)	0.0189 (7)	0.0288 (7)	0.0194 (7)
O4	0.0565 (9)	0.0663 (10)	0.0652 (9)	0.0131 (7)	0.0337 (8)	−0.0070 (7)
O5	0.0816 (11)	0.0672 (11)	0.0990 (12)	0.0332 (10)	0.0598 (10)	0.0241 (10)
O6	0.0539 (8)	0.0517 (8)	0.0504 (7)	0.0009 (6)	0.0336 (6)	−0.0049 (6)
O7	0.1111 (16)	0.147 (2)	0.168 (2)	−0.0384 (15)	0.1127 (17)	−0.0539 (17)
N1	0.0707 (13)	0.0618 (12)	0.0463 (9)	0.0036 (10)	0.0344 (10)	0.0117 (8)
N2	0.0595 (10)	0.0535 (10)	0.0452 (9)	0.0048 (8)	0.0329 (8)	0.0101 (8)
C1	0.0458 (10)	0.0417 (11)	0.0455 (10)	0.0049 (9)	0.0243 (8)	0.0054 (8)
C2	0.0513 (12)	0.0427 (11)	0.0716 (14)	0.0046 (10)	0.0344 (11)	0.0151 (10)
C3	0.0461 (12)	0.0394 (11)	0.0857 (16)	−0.0037 (9)	0.0236 (11)	0.0010 (11)
C4	0.0544 (12)	0.0457 (12)	0.0576 (12)	−0.0020 (10)	0.0154 (10)	−0.0095 (10)
C5	0.0483 (11)	0.0429 (11)	0.0426 (10)	0.0018 (9)	0.0197 (9)	0.0018 (8)
C6	0.0370 (9)	0.0351 (10)	0.0390 (9)	0.0056 (8)	0.0189 (7)	0.0042 (8)
C7	0.0407 (10)	0.0380 (10)	0.0337 (8)	−0.0013 (8)	0.0193 (7)	−0.0010 (7)
C8	0.0390 (9)	0.0382 (10)	0.0396 (9)	−0.0028 (8)	0.0202 (8)	−0.0053 (8)
C9	0.0413 (10)	0.0425 (10)	0.0445 (10)	−0.0043 (8)	0.0204 (8)	−0.0093 (8)
C10	0.0570 (13)	0.0593 (14)	0.0749 (15)	0.0143 (11)	0.0204 (11)	0.0193 (12)
C11	0.0476 (11)	0.0429 (10)	0.0453 (10)	−0.0015 (9)	0.0266 (9)	−0.0039 (9)
C12	0.0691 (14)	0.0687 (15)	0.0635 (13)	0.0036 (12)	0.0471 (12)	0.0042 (11)
C13	0.0459 (10)	0.0374 (10)	0.0463 (10)	−0.0023 (8)	0.0226 (8)	0.0009 (8)
C14	0.0676 (14)	0.0519 (13)	0.0651 (13)	0.0070 (11)	0.0321 (11)	0.0172 (11)
C15	0.0422 (10)	0.0333 (9)	0.0436 (9)	−0.0019 (8)	0.0232 (8)	−0.0023 (8)
C16	0.0510 (11)	0.0370 (10)	0.0575 (11)	−0.0026 (9)	0.0306 (9)	−0.0027 (9)
C17	0.0625 (13)	0.0666 (14)	0.0584 (12)	−0.0052 (11)	0.0407 (11)	−0.0140 (11)
C18	0.0650 (14)	0.0682 (15)	0.0780 (15)	−0.0065 (12)	0.0486 (13)	−0.0040 (12)
C19	0.0551 (14)	0.0798 (18)	0.0935 (18)	−0.0130 (13)	0.0290 (13)	−0.0135 (15)

Geometric parameters (Å, º)

O1—N1	1.226 (2)	C7—C8	1.528 (2)
O2—N1	1.217 (2)	C7—H7	0.9800
O3—C9	1.331 (2)	C8—C11	1.350 (3)
O3—C10	1.435 (2)	C8—C9	1.459 (3)
O4—C9	1.216 (2)	C10—H10A	0.9600
O5—C16	1.204 (2)	C10—H10B	0.9600
O6—C16	1.353 (2)	C10—H10C	0.9600
O6—C17	1.436 (2)	C11—C12	1.501 (3)
O7—C18	1.204 (3)	C12—H12A	0.9600
N1—C1	1.475 (3)	C12—H12B	0.9600
N2—C11	1.373 (3)	C12—H12C	0.9600
N2—C13	1.374 (2)	C13—C15	1.350 (3)
N2—H2A	0.8600	C13—C14	1.499 (3)
C1—C2	1.381 (3)	C14—H14A	0.9600
C1—C6	1.396 (2)	C14—H14B	0.9600
C2—C3	1.369 (3)	C14—H14C	0.9600
C2—H2	0.9300	C15—C16	1.462 (3)
C3—C4	1.374 (3)	C17—C18	1.490 (3)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.386 (3)	C17—H17B	0.9700
C4—H4	0.9300	C18—C19	1.482 (3)
C5—C6	1.387 (3)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.536 (2)	C19—H19C	0.9600
C7—C15	1.528 (3)
C9—O3—C10	116.91 (16)	H10A—C10—H10C	109.5
C16—O6—C17	115.43 (16)	H10B—C10—H10C	109.5
O2—N1—O1	123.36 (19)	C8—C11—N2	119.83 (16)
O2—N1—C1	119.75 (16)	C8—C11—C12	127.00 (18)
O1—N1—C1	116.88 (19)	N2—C11—C12	113.16 (17)
C11—N2—C13	124.25 (16)	C11—C12—H12A	109.5
C11—N2—H2A	117.9	C11—C12—H12B	109.5
C13—N2—H2A	117.9	H12A—C12—H12B	109.5
C2—C1—C6	122.86 (18)	C11—C12—H12C	109.5
C2—C1—N1	114.83 (17)	H12A—C12—H12C	109.5
C6—C1—N1	122.31 (17)	H12B—C12—H12C	109.5
C3—C2—C1	119.83 (19)	C15—C13—N2	119.73 (17)
C3—C2—H2	120.1	C15—C13—C14	127.27 (17)
C1—C2—H2	120.1	N2—C13—C14	112.97 (16)
C2—C3—C4	119.3 (2)	C13—C14—H14A	109.5
C2—C3—H3	120.3	C13—C14—H14B	109.5
C4—C3—H3	120.3	H14A—C14—H14B	109.5
C3—C4—C5	120.2 (2)	C13—C14—H14C	109.5
C3—C4—H4	119.9	H14A—C14—H14C	109.5
C5—C4—H4	119.9	H14B—C14—H14C	109.5
C4—C5—C6	122.30 (18)	C13—C15—C16	119.23 (17)
C4—C5—H5	118.9	C13—C15—C7	121.74 (16)
C6—C5—H5	118.9	C16—C15—C7	119.03 (15)
C5—C6—C1	115.46 (17)	O5—C16—O6	120.52 (17)
C5—C6—C7	117.70 (15)	O5—C16—C15	128.37 (19)
C1—C6—C7	126.67 (16)	O6—C16—C15	111.10 (17)
C15—C7—C8	111.45 (14)	O6—C17—C18	115.68 (18)
C15—C7—C6	109.09 (14)	O6—C17—H17A	108.4
C8—C7—C6	110.53 (14)	C18—C17—H17A	108.4
C15—C7—H7	108.6	O6—C17—H17B	108.4
C8—C7—H7	108.6	C18—C17—H17B	108.4
C6—C7—H7	108.6	H17A—C17—H17B	107.4
C11—C8—C9	120.31 (16)	O7—C18—C19	122.6 (2)
C11—C8—C7	121.78 (16)	O7—C18—C17	116.1 (2)
C9—C8—C7	117.88 (15)	C19—C18—C17	121.35 (19)
O4—C9—O3	120.99 (18)	C18—C19—H19A	109.5
O4—C9—C8	127.59 (18)	C18—C19—H19B	109.5
O3—C9—C8	111.42 (15)	H19A—C19—H19B	109.5
O3—C10—H10A	109.5	C18—C19—H19C	109.5
O3—C10—H10B	109.5	H19A—C19—H19C	109.5
H10A—C10—H10B	109.5	H19B—C19—H19C	109.5
O3—C10—H10C	109.5
O2—N1—C1—C2	138.5 (2)	C11—C8—C9—O3	173.44 (16)
O1—N1—C1—C2	−40.6 (3)	C7—C8—C9—O3	−8.3 (2)
O2—N1—C1—C6	−41.6 (3)	C9—C8—C11—N2	178.55 (17)
O1—N1—C1—C6	139.3 (2)	C7—C8—C11—N2	0.4 (3)
C6—C1—C2—C3	1.2 (3)	C9—C8—C11—C12	−2.5 (3)
N1—C1—C2—C3	−178.86 (18)	C7—C8—C11—C12	179.32 (18)
C1—C2—C3—C4	−1.3 (3)	C13—N2—C11—C8	7.6 (3)
C2—C3—C4—C5	0.4 (3)	C13—N2—C11—C12	−171.52 (18)
C3—C4—C5—C6	0.7 (3)	C11—N2—C13—C15	−5.1 (3)
C4—C5—C6—C1	−0.7 (3)	C11—N2—C13—C14	173.15 (18)
C4—C5—C6—C7	−176.21 (17)	N2—C13—C15—C16	174.21 (16)
C2—C1—C6—C5	−0.2 (3)	C14—C13—C15—C16	−3.8 (3)
N1—C1—C6—C5	179.86 (17)	N2—C13—C15—C7	−5.1 (3)
C2—C1—C6—C7	174.79 (17)	C14—C13—C15—C7	176.91 (18)
N1—C1—C6—C7	−5.1 (3)	C8—C7—C15—C13	11.3 (2)
C5—C6—C7—C15	70.67 (19)	C6—C7—C15—C13	−110.98 (18)
C1—C6—C7—C15	−104.27 (19)	C8—C7—C15—C16	−167.96 (15)
C5—C6—C7—C8	−52.2 (2)	C6—C7—C15—C16	69.7 (2)
C1—C6—C7—C8	132.86 (18)	C17—O6—C16—O5	−4.9 (3)
C15—C7—C8—C11	−9.0 (2)	C17—O6—C16—C15	174.14 (15)
C6—C7—C8—C11	112.52 (19)	C13—C15—C16—O5	4.8 (3)
C15—C7—C8—C9	172.83 (15)	C7—C15—C16—O5	−175.9 (2)
C6—C7—C8—C9	−65.68 (19)	C13—C15—C16—O6	−174.20 (16)
C10—O3—C9—O4	−1.8 (3)	C7—C15—C16—O6	5.1 (2)
C10—O3—C9—C8	177.28 (17)	C16—O6—C17—C18	83.7 (2)
C11—C8—C9—O4	−7.6 (3)	O6—C17—C18—O7	178.5 (2)
C7—C8—C9—O4	170.64 (18)	O6—C17—C18—C19	−1.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4^i	0.86	2.16	2.958 (2)	154
C2—H2···O7^ii	0.93	2.44	3.237 (4)	144

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