2,3-Di­methyl 5-iso­propyl 1-ethoxy­methyl-6-methyl-4-(3-nitro­phenyl)-1,4-di­hydro­pyridine-2,3,5-tri­carboxyl­ate

In the title compound, C₂₃H₂₈N₂O₉, the substituted 1,4-di­hydro­pyridine ring has a flat-boat conformation. The dihedral angle between the mean planes of the 1,4-di­hydro­pyridine and substituted phenyl rings is 88.10 (9)°. The 3-nitro substituent on the phenyl ring is rotated from coplanarity with the ring by only 3.2 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.083
• Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: Syntex P2₁ software; cell refinement: Syntex P2₁ software; data reduction: XP21 (Pavelčík, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXS97.

2,3-Dimethyl 5-isopropyl 1-ethoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4- dihydropyridine-2,3,5-tricarboxylate

Crystal data

C23H28N2O9	F(000) = 1008
Mr = 476.47	Dx = 1.325 Mg m^−3 Dm = 1.33 (1) Mg m^−3 Dm measured by flotation in bromoform–hexane
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.291 (4) Å	θ = 6.9–18.7°
b = 9.589 (3) Å	µ = 0.10 mm^−1
c = 27.175 (13) Å	T = 293 K
β = 99.53 (3)°	Block, yellow
V = 2387.6 (17) Å^3	0.4 × 0.3 × 0.3 mm
Z = 4

Data collection

Syntex P21 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 27.6°, θmin = 1.5°
Graphite monochromator	h = 0→12
θ/2θ scans	k = 0→12
5519 measured reflections	l = −35→34
5519 independent reflections	2 standard reflections every 100 min
1503 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0187P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.004
5519 reflections	Δρmax = 0.21 e Å^−3
313 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (2)

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

	x	y	z	Uiso*/Ueq
O1	0.7279 (3)	−0.4152 (2)	0.67898 (9)	0.0956 (7)
O2	0.5845 (2)	−0.2275 (2)	0.79432 (6)	0.0943 (8)
O3	0.8117 (2)	−0.23776 (18)	0.77752 (6)	0.0681 (6)
O4	0.74316 (19)	0.05575 (17)	0.78769 (5)	0.0746 (6)
O5	0.7679 (2)	0.1972 (2)	0.72510 (6)	0.0647 (6)
O6	0.7651 (2)	0.3403 (2)	0.51954 (7)	0.0844 (7)
O7	0.9599 (2)	0.2487 (2)	0.50037 (6)	0.0872 (7)
O8	0.2915 (2)	−0.04339 (18)	0.55522 (7)	0.0818 (7)
O9	0.41566 (17)	0.14887 (18)	0.57961 (5)	0.0509 (5)
N1	0.5540 (2)	−0.2373 (2)	0.68197 (7)	0.0527 (6)
N2	0.8597 (3)	0.2523 (3)	0.52454 (8)	0.0626 (7)
C1	0.6297 (3)	−0.1459 (3)	0.71601 (8)	0.0460 (7)
C2	0.6513 (3)	−0.0145 (3)	0.70464 (8)	0.0426 (7)
C3	0.6097 (2)	0.0382 (2)	0.65277 (7)	0.0414 (6)
H3	0.5743	0.1341	0.6545	0.050*
C4	0.4848 (2)	−0.0502 (3)	0.62581 (8)	0.0410 (7)
C5	0.4680 (3)	−0.1832 (3)	0.63865 (9)	0.0454 (7)
C6	0.5879 (3)	−0.3856 (3)	0.68790 (10)	0.0710 (9)
H6A	0.5795	−0.4142	0.7215	0.085*
H6B	0.5176	−0.4386	0.6649	0.085*
C7	0.7411 (4)	−0.4476 (4)	0.63160 (12)	0.1120 (13)
H7A	0.7024	−0.3719	0.6096	0.134*
H7B	0.6843	−0.5306	0.6213	0.134*
C8	0.8964 (4)	−0.4725 (3)	0.62678 (11)	0.1196 (12)
H8A	0.9024	−0.4955	0.5928	0.179*
H8B	0.9344	−0.5482	0.6481	0.179*
H8C	0.9523	−0.3898	0.6363	0.179*
C9	0.6712 (4)	−0.2069 (3)	0.76746 (9)	0.0589 (8)
C10	0.8600 (3)	−0.2995 (3)	0.82578 (9)	0.1065 (12)
H10A	0.9615	−0.3234	0.8290	0.160*
H10B	0.8041	−0.3822	0.8291	0.160*
H10C	0.8467	−0.2342	0.8514	0.160*
C11	0.7239 (3)	0.0806 (3)	0.74377 (10)	0.0544 (8)
C12	0.8348 (3)	0.2998 (3)	0.76061 (9)	0.0950 (11)
H12A	0.8479	0.3853	0.7435	0.142*
H12B	0.9279	0.2661	0.7769	0.142*
H12C	0.7729	0.3162	0.7850	0.142*
C13	0.7348 (3)	0.0391 (3)	0.62293 (8)	0.0386 (6)
C14	0.7456 (3)	0.1443 (2)	0.58971 (8)	0.0412 (7)
H14	0.6801	0.2184	0.5865	0.049*
C15	0.8547 (3)	0.1393 (3)	0.56097 (9)	0.0455 (7)
C16	0.9559 (3)	0.0352 (3)	0.56523 (9)	0.0543 (7)
H16	1.0293	0.0345	0.5457	0.065*
C17	0.9460 (3)	−0.0681 (3)	0.59904 (9)	0.0535 (7)
H17	1.0129	−0.1410	0.6026	0.064*
C18	0.8373 (3)	−0.0647 (3)	0.62785 (8)	0.0499 (7)
H18	0.8335	−0.1347	0.6513	0.060*
C19	0.3870 (3)	0.0138 (3)	0.58384 (9)	0.0484 (7)
C20	0.3283 (3)	0.2257 (3)	0.53940 (9)	0.0625 (8)
H20	0.2266	0.1943	0.5352	0.075*
C21	0.3386 (4)	0.3747 (3)	0.55625 (10)	0.1195 (13)
H21A	0.2668	0.4292	0.5351	0.179*
H21B	0.4342	0.4100	0.5544	0.179*
H21C	0.3214	0.3802	0.5901	0.179*
C22	0.3874 (3)	0.2032 (3)	0.49220 (9)	0.1130 (12)
H22A	0.4856	0.2379	0.4961	0.170*
H22B	0.3278	0.2518	0.4654	0.170*
H22C	0.3870	0.1053	0.4848	0.170*
C23	0.3559 (3)	−0.2825 (2)	0.61175 (8)	0.0640 (8)
H23A	0.3654	−0.3715	0.6282	0.096*
H23B	0.3711	−0.2933	0.5779	0.096*
H23C	0.2599	−0.2460	0.6121	0.096*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0896 (18)	0.0818 (16)	0.1119 (17)	0.0077 (15)	0.0063 (16)	−0.0159 (14)
O2	0.0787 (15)	0.144 (2)	0.0624 (12)	−0.0194 (15)	0.0183 (11)	0.0406 (13)
O3	0.0605 (14)	0.0805 (15)	0.0590 (11)	0.0127 (13)	−0.0025 (10)	0.0183 (11)
O4	0.1057 (16)	0.0789 (15)	0.0357 (10)	−0.0017 (13)	0.0012 (11)	−0.0031 (11)
O5	0.0820 (15)	0.0591 (13)	0.0509 (11)	−0.0178 (12)	0.0053 (10)	−0.0026 (11)
O6	0.0968 (18)	0.0739 (16)	0.0874 (15)	0.0177 (14)	0.0293 (14)	0.0347 (13)
O7	0.0755 (16)	0.1144 (18)	0.0783 (13)	−0.0121 (15)	0.0321 (13)	0.0256 (13)
O8	0.0690 (14)	0.0651 (15)	0.0963 (14)	−0.0141 (13)	−0.0299 (12)	0.0100 (11)
O9	0.0565 (13)	0.0417 (11)	0.0502 (10)	−0.0002 (11)	−0.0045 (9)	0.0048 (10)
N1	0.0580 (16)	0.0440 (15)	0.0540 (14)	−0.0009 (14)	0.0030 (12)	0.0134 (13)
N2	0.064 (2)	0.072 (2)	0.0507 (15)	−0.0132 (18)	0.0059 (15)	0.0115 (16)
C1	0.0419 (18)	0.058 (2)	0.0380 (16)	−0.0013 (17)	0.0062 (14)	0.0040 (17)
C2	0.0423 (18)	0.0473 (19)	0.0383 (15)	0.0006 (15)	0.0069 (14)	0.0015 (14)
C3	0.0434 (16)	0.0392 (17)	0.0415 (14)	0.0015 (15)	0.0067 (14)	−0.0021 (14)
C4	0.0368 (16)	0.049 (2)	0.0367 (14)	−0.0013 (17)	0.0054 (13)	0.0044 (15)
C5	0.0426 (18)	0.0444 (19)	0.0505 (17)	−0.0043 (16)	0.0114 (15)	0.0008 (15)
C6	0.071 (2)	0.059 (2)	0.081 (2)	0.001 (2)	0.0070 (19)	0.0130 (17)
C7	0.117 (3)	0.136 (3)	0.079 (2)	−0.014 (3)	0.004 (2)	−0.029 (2)
C8	0.099 (3)	0.125 (3)	0.134 (3)	0.026 (3)	0.015 (2)	−0.034 (2)
C9	0.066 (2)	0.061 (2)	0.0471 (19)	−0.009 (2)	0.0012 (18)	0.0111 (16)
C10	0.111 (3)	0.124 (3)	0.0708 (19)	0.014 (2)	−0.0276 (19)	0.049 (2)
C11	0.0549 (19)	0.064 (2)	0.0442 (17)	0.0036 (18)	0.0083 (16)	−0.0035 (19)
C12	0.133 (3)	0.077 (2)	0.0686 (19)	−0.042 (2)	−0.003 (2)	−0.0202 (18)
C13	0.0413 (16)	0.0387 (17)	0.0344 (14)	0.0071 (16)	0.0025 (13)	0.0036 (13)
C14	0.0424 (17)	0.0434 (17)	0.0379 (13)	0.0018 (15)	0.0066 (14)	−0.0005 (14)
C15	0.0446 (18)	0.0453 (19)	0.0444 (16)	−0.0079 (17)	0.0007 (15)	0.0027 (16)
C16	0.0446 (18)	0.070 (2)	0.0502 (16)	−0.0078 (19)	0.0132 (15)	−0.0029 (17)
C17	0.0486 (19)	0.054 (2)	0.0594 (16)	0.0080 (17)	0.0126 (16)	0.0010 (16)
C18	0.0547 (18)	0.0517 (19)	0.0437 (15)	−0.0024 (18)	0.0096 (14)	0.0043 (15)
C19	0.0456 (19)	0.046 (2)	0.0531 (18)	0.0016 (18)	0.0081 (15)	−0.0007 (16)
C20	0.0489 (18)	0.057 (2)	0.073 (2)	0.0017 (18)	−0.0140 (16)	0.0155 (18)
C21	0.188 (4)	0.049 (2)	0.106 (2)	0.013 (3)	−0.020 (2)	0.0113 (19)
C22	0.117 (3)	0.151 (3)	0.0637 (19)	0.003 (3)	−0.004 (2)	0.032 (2)
C23	0.068 (2)	0.0572 (19)	0.0640 (17)	−0.0137 (18)	0.0024 (16)	0.0047 (15)

Geometric parameters (Å, º)

O1—C7	1.350 (3)	C8—H8A	0.9600
O1—C6	1.391 (3)	C8—H8B	0.9600
O2—C9	1.190 (3)	C8—H8C	0.9600
O3—C9	1.322 (3)	C10—H10A	0.9600
O3—C10	1.441 (2)	C10—H10B	0.9600
O4—C11	1.201 (2)	C10—H10C	0.9600
O5—C11	1.321 (3)	C12—H12A	0.9600
O5—C12	1.445 (2)	C12—H12B	0.9600
O6—N2	1.210 (3)	C12—H12C	0.9600
O7—N2	1.225 (2)	C13—C14	1.369 (3)
O8—C19	1.211 (3)	C13—C18	1.369 (3)
O9—C19	1.331 (3)	C14—C15	1.380 (3)
O9—C20	1.450 (2)	C14—H14	0.9300
N1—C1	1.380 (3)	C15—C16	1.363 (3)
N1—C5	1.408 (3)	C16—C17	1.364 (3)
N1—C6	1.459 (3)	C16—H16	0.9300
N2—C15	1.474 (3)	C17—C18	1.376 (3)
C1—C2	1.320 (3)	C17—H17	0.9300
C1—C9	1.506 (3)	C18—H18	0.9300
C2—C11	1.476 (3)	C20—C22	1.492 (3)
C2—C3	1.487 (3)	C20—C21	1.498 (3)
C3—C4	1.523 (3)	C20—H20	0.9800
C3—C13	1.523 (3)	C21—H21A	0.9600
C3—H3	0.9800	C21—H21B	0.9600
C4—C5	1.339 (3)	C21—H21C	0.9600
C4—C19	1.470 (3)	C22—H22A	0.9600
C5—C23	1.508 (3)	C22—H22B	0.9600
C6—H6A	0.9700	C22—H22C	0.9600
C6—H6B	0.9700	C23—H23A	0.9600
C7—C8	1.489 (4)	C23—H23B	0.9600
C7—H7A	0.9700	C23—H23C	0.9600
C7—H7B	0.9700
C7—O1—C6	116.7 (3)	O4—C11—O5	123.0 (3)
C9—O3—C10	115.4 (2)	O4—C11—C2	124.7 (3)
C11—O5—C12	116.52 (19)	O5—C11—C2	112.3 (2)
C19—O9—C20	117.7 (2)	O5—C12—H12A	109.5
C1—N1—C5	118.8 (2)	O5—C12—H12B	109.5
C1—N1—C6	117.9 (2)	H12A—C12—H12B	109.5
C5—N1—C6	122.2 (2)	O5—C12—H12C	109.5
O6—N2—O7	124.2 (3)	H12A—C12—H12C	109.5
O6—N2—C15	119.0 (3)	H12B—C12—H12C	109.5
O7—N2—C15	116.8 (3)	C14—C13—C18	118.3 (2)
C2—C1—N1	122.0 (2)	C14—C13—C3	120.1 (2)
C2—C1—C9	124.2 (3)	C18—C13—C3	121.6 (2)
N1—C1—C9	113.5 (2)	C13—C14—C15	119.3 (2)
C1—C2—C11	119.3 (2)	C13—C14—H14	120.4
C1—C2—C3	121.4 (2)	C15—C14—H14	120.4
C11—C2—C3	119.3 (2)	C16—C15—C14	122.6 (2)
C2—C3—C4	109.0 (2)	C16—C15—N2	119.9 (3)
C2—C3—C13	113.86 (19)	C14—C15—N2	117.5 (3)
C4—C3—C13	109.53 (17)	C15—C16—C17	117.8 (2)
C2—C3—H3	108.1	C15—C16—H16	121.1
C4—C3—H3	108.1	C17—C16—H16	121.1
C13—C3—H3	108.1	C16—C17—C18	120.2 (2)
C5—C4—C19	121.1 (3)	C16—C17—H17	119.9
C5—C4—C3	121.2 (2)	C18—C17—H17	119.9
C19—C4—C3	117.7 (2)	C13—C18—C17	121.7 (2)
C4—C5—N1	119.6 (2)	C13—C18—H18	119.1
C4—C5—C23	125.2 (2)	C17—C18—H18	119.1
N1—C5—C23	115.1 (2)	O8—C19—O9	121.4 (2)
O1—C6—N1	111.8 (2)	O8—C19—C4	127.1 (3)
O1—C6—H6A	109.3	O9—C19—C4	111.5 (3)
N1—C6—H6A	109.3	O9—C20—C22	109.5 (2)
O1—C6—H6B	109.3	O9—C20—C21	104.8 (2)
N1—C6—H6B	109.3	C22—C20—C21	112.8 (3)
H6A—C6—H6B	107.9	O9—C20—H20	109.9
O1—C7—C8	111.3 (3)	C22—C20—H20	109.9
O1—C7—H7A	109.4	C21—C20—H20	109.9
C8—C7—H7A	109.4	C20—C21—H21A	109.5
O1—C7—H7B	109.4	C20—C21—H21B	109.5
C8—C7—H7B	109.4	H21A—C21—H21B	109.5
H7A—C7—H7B	108.0	C20—C21—H21C	109.5
C7—C8—H8A	109.5	H21A—C21—H21C	109.5
C7—C8—H8B	109.5	H21B—C21—H21C	109.5
H8A—C8—H8B	109.5	C20—C22—H22A	109.5
C7—C8—H8C	109.5	C20—C22—H22B	109.5
H8A—C8—H8C	109.5	H22A—C22—H22B	109.5
H8B—C8—H8C	109.5	C20—C22—H22C	109.5
O2—C9—O3	125.5 (3)	H22A—C22—H22C	109.5
O2—C9—C1	122.6 (3)	H22B—C22—H22C	109.5
O3—C9—C1	111.8 (2)	C5—C23—H23A	109.5
O3—C10—H10A	109.5	C5—C23—H23B	109.5
O3—C10—H10B	109.5	H23A—C23—H23B	109.5
H10A—C10—H10B	109.5	C5—C23—H23C	109.5
O3—C10—H10C	109.5	H23A—C23—H23C	109.5
H10A—C10—H10C	109.5	H23B—C23—H23C	109.5
H10B—C10—H10C	109.5
C5—N1—C1—C2	−15.6 (3)	N1—C1—C9—O3	105.3 (3)
C6—N1—C1—C2	153.2 (3)	C12—O5—C11—O4	−3.4 (4)
C5—N1—C1—C9	159.0 (2)	C12—O5—C11—C2	177.4 (2)
C6—N1—C1—C9	−32.2 (3)	C1—C2—C11—O4	−13.8 (4)
N1—C1—C2—C11	175.6 (2)	C3—C2—C11—O4	168.8 (2)
C9—C1—C2—C11	1.6 (4)	C1—C2—C11—O5	165.4 (2)
N1—C1—C2—C3	−7.0 (4)	C3—C2—C11—O5	−12.0 (3)
C9—C1—C2—C3	179.0 (2)	C2—C3—C13—C14	−143.6 (2)
C1—C2—C3—C4	26.8 (3)	C4—C3—C13—C14	94.1 (3)
C11—C2—C3—C4	−155.7 (2)	C2—C3—C13—C18	37.3 (3)
C1—C2—C3—C13	−95.8 (3)	C4—C3—C13—C18	−84.9 (2)
C11—C2—C3—C13	81.7 (3)	C18—C13—C14—C15	2.8 (3)
C2—C3—C4—C5	−27.8 (3)	C3—C13—C14—C15	−176.36 (19)
C13—C3—C4—C5	97.3 (3)	C13—C14—C15—C16	−1.9 (3)
C2—C3—C4—C19	154.7 (2)	C13—C14—C15—N2	178.11 (19)
C13—C3—C4—C19	−80.1 (2)	O6—N2—C15—C16	176.5 (2)
C19—C4—C5—N1	−173.71 (19)	O7—N2—C15—C16	−2.1 (3)
C3—C4—C5—N1	8.9 (3)	O6—N2—C15—C14	−3.5 (3)
C19—C4—C5—C23	2.6 (4)	O7—N2—C15—C14	177.8 (2)
C3—C4—C5—C23	−174.8 (2)	C14—C15—C16—C17	0.8 (4)
C1—N1—C5—C4	14.2 (3)	N2—C15—C16—C17	−179.3 (2)
C6—N1—C5—C4	−154.1 (3)	C15—C16—C17—C18	−0.5 (4)
C1—N1—C5—C23	−162.4 (2)	C14—C13—C18—C17	−2.6 (3)
C6—N1—C5—C23	29.2 (3)	C3—C13—C18—C17	176.5 (2)
C7—O1—C6—N1	−90.3 (3)	C16—C17—C18—C13	1.5 (4)
C1—N1—C6—O1	−67.5 (3)	C20—O9—C19—O8	0.0 (3)
C5—N1—C6—O1	101.0 (3)	C20—O9—C19—C4	179.48 (18)
C6—O1—C7—C8	178.2 (3)	C5—C4—C19—O8	−5.0 (4)
C10—O3—C9—O2	−1.0 (4)	C3—C4—C19—O8	172.4 (2)
C10—O3—C9—C1	−178.8 (2)	C5—C4—C19—O9	175.5 (2)
C2—C1—C9—O2	101.9 (4)	C3—C4—C19—O9	−7.0 (3)
N1—C1—C9—O2	−72.6 (4)	C19—O9—C20—C22	−82.1 (3)
C2—C1—C9—O3	−80.3 (3)	C19—O9—C20—C21	156.7 (2)