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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)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003015/lh6034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003015/lh6034Isup2.hkl
Contains datablock I

CCDC reference: 206771

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








Computing details top

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 top
Crystal data top
C23H28N2O9F(000) = 1008
Mr = 476.47Dx = 1.325 Mg m3
Dm = 1.33 (1) Mg m3
Dm measured by flotation in bromoform–hexane
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.291 (4) Åθ = 6.9–18.7°
b = 9.589 (3) ŵ = 0.10 mm1
c = 27.175 (13) ÅT = 293 K
β = 99.53 (3)°Block, yellow
V = 2387.6 (17) Å30.4 × 0.3 × 0.3 mm
Z = 4
Data collection top
Syntex P21
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 27.6°, θmin = 1.5°
Graphite monochromatorh = 012
θ/2θ scansk = 012
5519 measured reflectionsl = 3534
5519 independent reflections2 standard reflections every 100 min
1503 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0187P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.004
5519 reflectionsΔρmax = 0.21 e Å3
313 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7279 (3)0.4152 (2)0.67898 (9)0.0956 (7)
O20.5845 (2)0.2275 (2)0.79432 (6)0.0943 (8)
O30.8117 (2)0.23776 (18)0.77752 (6)0.0681 (6)
O40.74316 (19)0.05575 (17)0.78769 (5)0.0746 (6)
O50.7679 (2)0.1972 (2)0.72510 (6)0.0647 (6)
O60.7651 (2)0.3403 (2)0.51954 (7)0.0844 (7)
O70.9599 (2)0.2487 (2)0.50037 (6)0.0872 (7)
O80.2915 (2)0.04339 (18)0.55522 (7)0.0818 (7)
O90.41566 (17)0.14887 (18)0.57961 (5)0.0509 (5)
N10.5540 (2)0.2373 (2)0.68197 (7)0.0527 (6)
N20.8597 (3)0.2523 (3)0.52454 (8)0.0626 (7)
C10.6297 (3)0.1459 (3)0.71601 (8)0.0460 (7)
C20.6513 (3)0.0145 (3)0.70464 (8)0.0426 (7)
C30.6097 (2)0.0382 (2)0.65277 (7)0.0414 (6)
H30.57430.13410.65450.050*
C40.4848 (2)0.0502 (3)0.62581 (8)0.0410 (7)
C50.4680 (3)0.1832 (3)0.63865 (9)0.0454 (7)
C60.5879 (3)0.3856 (3)0.68790 (10)0.0710 (9)
H6A0.57950.41420.72150.085*
H6B0.51760.43860.66490.085*
C70.7411 (4)0.4476 (4)0.63160 (12)0.1120 (13)
H7A0.70240.37190.60960.134*
H7B0.68430.53060.62130.134*
C80.8964 (4)0.4725 (3)0.62678 (11)0.1196 (12)
H8A0.90240.49550.59280.179*
H8B0.93440.54820.64810.179*
H8C0.95230.38980.63630.179*
C90.6712 (4)0.2069 (3)0.76746 (9)0.0589 (8)
C100.8600 (3)0.2995 (3)0.82578 (9)0.1065 (12)
H10A0.96150.32340.82900.160*
H10B0.80410.38220.82910.160*
H10C0.84670.23420.85140.160*
C110.7239 (3)0.0806 (3)0.74377 (10)0.0544 (8)
C120.8348 (3)0.2998 (3)0.76061 (9)0.0950 (11)
H12A0.84790.38530.74350.142*
H12B0.92790.26610.77690.142*
H12C0.77290.31620.78500.142*
C130.7348 (3)0.0391 (3)0.62293 (8)0.0386 (6)
C140.7456 (3)0.1443 (2)0.58971 (8)0.0412 (7)
H140.68010.21840.58650.049*
C150.8547 (3)0.1393 (3)0.56097 (9)0.0455 (7)
C160.9559 (3)0.0352 (3)0.56523 (9)0.0543 (7)
H161.02930.03450.54570.065*
C170.9460 (3)0.0681 (3)0.59904 (9)0.0535 (7)
H171.01290.14100.60260.064*
C180.8373 (3)0.0647 (3)0.62785 (8)0.0499 (7)
H180.83350.13470.65130.060*
C190.3870 (3)0.0138 (3)0.58384 (9)0.0484 (7)
C200.3283 (3)0.2257 (3)0.53940 (9)0.0625 (8)
H200.22660.19430.53520.075*
C210.3386 (4)0.3747 (3)0.55625 (10)0.1195 (13)
H21A0.26680.42920.53510.179*
H21B0.43420.41000.55440.179*
H21C0.32140.38020.59010.179*
C220.3874 (3)0.2032 (3)0.49220 (9)0.1130 (12)
H22A0.48560.23790.49610.170*
H22B0.32780.25180.46540.170*
H22C0.38700.10530.48480.170*
C230.3559 (3)0.2825 (2)0.61175 (8)0.0640 (8)
H23A0.36540.37150.62820.096*
H23B0.37110.29330.57790.096*
H23C0.25990.24600.61210.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0896 (18)0.0818 (16)0.1119 (17)0.0077 (15)0.0063 (16)0.0159 (14)
O20.0787 (15)0.144 (2)0.0624 (12)0.0194 (15)0.0183 (11)0.0406 (13)
O30.0605 (14)0.0805 (15)0.0590 (11)0.0127 (13)0.0025 (10)0.0183 (11)
O40.1057 (16)0.0789 (15)0.0357 (10)0.0017 (13)0.0012 (11)0.0031 (11)
O50.0820 (15)0.0591 (13)0.0509 (11)0.0178 (12)0.0053 (10)0.0026 (11)
O60.0968 (18)0.0739 (16)0.0874 (15)0.0177 (14)0.0293 (14)0.0347 (13)
O70.0755 (16)0.1144 (18)0.0783 (13)0.0121 (15)0.0321 (13)0.0256 (13)
O80.0690 (14)0.0651 (15)0.0963 (14)0.0141 (13)0.0299 (12)0.0100 (11)
O90.0565 (13)0.0417 (11)0.0502 (10)0.0002 (11)0.0045 (9)0.0048 (10)
N10.0580 (16)0.0440 (15)0.0540 (14)0.0009 (14)0.0030 (12)0.0134 (13)
N20.064 (2)0.072 (2)0.0507 (15)0.0132 (18)0.0059 (15)0.0115 (16)
C10.0419 (18)0.058 (2)0.0380 (16)0.0013 (17)0.0062 (14)0.0040 (17)
C20.0423 (18)0.0473 (19)0.0383 (15)0.0006 (15)0.0069 (14)0.0015 (14)
C30.0434 (16)0.0392 (17)0.0415 (14)0.0015 (15)0.0067 (14)0.0021 (14)
C40.0368 (16)0.049 (2)0.0367 (14)0.0013 (17)0.0054 (13)0.0044 (15)
C50.0426 (18)0.0444 (19)0.0505 (17)0.0043 (16)0.0114 (15)0.0008 (15)
C60.071 (2)0.059 (2)0.081 (2)0.001 (2)0.0070 (19)0.0130 (17)
C70.117 (3)0.136 (3)0.079 (2)0.014 (3)0.004 (2)0.029 (2)
C80.099 (3)0.125 (3)0.134 (3)0.026 (3)0.015 (2)0.034 (2)
C90.066 (2)0.061 (2)0.0471 (19)0.009 (2)0.0012 (18)0.0111 (16)
C100.111 (3)0.124 (3)0.0708 (19)0.014 (2)0.0276 (19)0.049 (2)
C110.0549 (19)0.064 (2)0.0442 (17)0.0036 (18)0.0083 (16)0.0035 (19)
C120.133 (3)0.077 (2)0.0686 (19)0.042 (2)0.003 (2)0.0202 (18)
C130.0413 (16)0.0387 (17)0.0344 (14)0.0071 (16)0.0025 (13)0.0036 (13)
C140.0424 (17)0.0434 (17)0.0379 (13)0.0018 (15)0.0066 (14)0.0005 (14)
C150.0446 (18)0.0453 (19)0.0444 (16)0.0079 (17)0.0007 (15)0.0027 (16)
C160.0446 (18)0.070 (2)0.0502 (16)0.0078 (19)0.0132 (15)0.0029 (17)
C170.0486 (19)0.054 (2)0.0594 (16)0.0080 (17)0.0126 (16)0.0010 (16)
C180.0547 (18)0.0517 (19)0.0437 (15)0.0024 (18)0.0096 (14)0.0043 (15)
C190.0456 (19)0.046 (2)0.0531 (18)0.0016 (18)0.0081 (15)0.0007 (16)
C200.0489 (18)0.057 (2)0.073 (2)0.0017 (18)0.0140 (16)0.0155 (18)
C210.188 (4)0.049 (2)0.106 (2)0.013 (3)0.020 (2)0.0113 (19)
C220.117 (3)0.151 (3)0.0637 (19)0.003 (3)0.004 (2)0.032 (2)
C230.068 (2)0.0572 (19)0.0640 (17)0.0137 (18)0.0024 (16)0.0047 (15)
Geometric parameters (Å, º) top
O1—C71.350 (3)C8—H8A0.9600
O1—C61.391 (3)C8—H8B0.9600
O2—C91.190 (3)C8—H8C0.9600
O3—C91.322 (3)C10—H10A0.9600
O3—C101.441 (2)C10—H10B0.9600
O4—C111.201 (2)C10—H10C0.9600
O5—C111.321 (3)C12—H12A0.9600
O5—C121.445 (2)C12—H12B0.9600
O6—N21.210 (3)C12—H12C0.9600
O7—N21.225 (2)C13—C141.369 (3)
O8—C191.211 (3)C13—C181.369 (3)
O9—C191.331 (3)C14—C151.380 (3)
O9—C201.450 (2)C14—H140.9300
N1—C11.380 (3)C15—C161.363 (3)
N1—C51.408 (3)C16—C171.364 (3)
N1—C61.459 (3)C16—H160.9300
N2—C151.474 (3)C17—C181.376 (3)
C1—C21.320 (3)C17—H170.9300
C1—C91.506 (3)C18—H180.9300
C2—C111.476 (3)C20—C221.492 (3)
C2—C31.487 (3)C20—C211.498 (3)
C3—C41.523 (3)C20—H200.9800
C3—C131.523 (3)C21—H21A0.9600
C3—H30.9800C21—H21B0.9600
C4—C51.339 (3)C21—H21C0.9600
C4—C191.470 (3)C22—H22A0.9600
C5—C231.508 (3)C22—H22B0.9600
C6—H6A0.9700C22—H22C0.9600
C6—H6B0.9700C23—H23A0.9600
C7—C81.489 (4)C23—H23B0.9600
C7—H7A0.9700C23—H23C0.9600
C7—H7B0.9700
C7—O1—C6116.7 (3)O4—C11—O5123.0 (3)
C9—O3—C10115.4 (2)O4—C11—C2124.7 (3)
C11—O5—C12116.52 (19)O5—C11—C2112.3 (2)
C19—O9—C20117.7 (2)O5—C12—H12A109.5
C1—N1—C5118.8 (2)O5—C12—H12B109.5
C1—N1—C6117.9 (2)H12A—C12—H12B109.5
C5—N1—C6122.2 (2)O5—C12—H12C109.5
O6—N2—O7124.2 (3)H12A—C12—H12C109.5
O6—N2—C15119.0 (3)H12B—C12—H12C109.5
O7—N2—C15116.8 (3)C14—C13—C18118.3 (2)
C2—C1—N1122.0 (2)C14—C13—C3120.1 (2)
C2—C1—C9124.2 (3)C18—C13—C3121.6 (2)
N1—C1—C9113.5 (2)C13—C14—C15119.3 (2)
C1—C2—C11119.3 (2)C13—C14—H14120.4
C1—C2—C3121.4 (2)C15—C14—H14120.4
C11—C2—C3119.3 (2)C16—C15—C14122.6 (2)
C2—C3—C4109.0 (2)C16—C15—N2119.9 (3)
C2—C3—C13113.86 (19)C14—C15—N2117.5 (3)
C4—C3—C13109.53 (17)C15—C16—C17117.8 (2)
C2—C3—H3108.1C15—C16—H16121.1
C4—C3—H3108.1C17—C16—H16121.1
C13—C3—H3108.1C16—C17—C18120.2 (2)
C5—C4—C19121.1 (3)C16—C17—H17119.9
C5—C4—C3121.2 (2)C18—C17—H17119.9
C19—C4—C3117.7 (2)C13—C18—C17121.7 (2)
C4—C5—N1119.6 (2)C13—C18—H18119.1
C4—C5—C23125.2 (2)C17—C18—H18119.1
N1—C5—C23115.1 (2)O8—C19—O9121.4 (2)
O1—C6—N1111.8 (2)O8—C19—C4127.1 (3)
O1—C6—H6A109.3O9—C19—C4111.5 (3)
N1—C6—H6A109.3O9—C20—C22109.5 (2)
O1—C6—H6B109.3O9—C20—C21104.8 (2)
N1—C6—H6B109.3C22—C20—C21112.8 (3)
H6A—C6—H6B107.9O9—C20—H20109.9
O1—C7—C8111.3 (3)C22—C20—H20109.9
O1—C7—H7A109.4C21—C20—H20109.9
C8—C7—H7A109.4C20—C21—H21A109.5
O1—C7—H7B109.4C20—C21—H21B109.5
C8—C7—H7B109.4H21A—C21—H21B109.5
H7A—C7—H7B108.0C20—C21—H21C109.5
C7—C8—H8A109.5H21A—C21—H21C109.5
C7—C8—H8B109.5H21B—C21—H21C109.5
H8A—C8—H8B109.5C20—C22—H22A109.5
C7—C8—H8C109.5C20—C22—H22B109.5
H8A—C8—H8C109.5H22A—C22—H22B109.5
H8B—C8—H8C109.5C20—C22—H22C109.5
O2—C9—O3125.5 (3)H22A—C22—H22C109.5
O2—C9—C1122.6 (3)H22B—C22—H22C109.5
O3—C9—C1111.8 (2)C5—C23—H23A109.5
O3—C10—H10A109.5C5—C23—H23B109.5
O3—C10—H10B109.5H23A—C23—H23B109.5
H10A—C10—H10B109.5C5—C23—H23C109.5
O3—C10—H10C109.5H23A—C23—H23C109.5
H10A—C10—H10C109.5H23B—C23—H23C109.5
H10B—C10—H10C109.5
C5—N1—C1—C215.6 (3)N1—C1—C9—O3105.3 (3)
C6—N1—C1—C2153.2 (3)C12—O5—C11—O43.4 (4)
C5—N1—C1—C9159.0 (2)C12—O5—C11—C2177.4 (2)
C6—N1—C1—C932.2 (3)C1—C2—C11—O413.8 (4)
N1—C1—C2—C11175.6 (2)C3—C2—C11—O4168.8 (2)
C9—C1—C2—C111.6 (4)C1—C2—C11—O5165.4 (2)
N1—C1—C2—C37.0 (4)C3—C2—C11—O512.0 (3)
C9—C1—C2—C3179.0 (2)C2—C3—C13—C14143.6 (2)
C1—C2—C3—C426.8 (3)C4—C3—C13—C1494.1 (3)
C11—C2—C3—C4155.7 (2)C2—C3—C13—C1837.3 (3)
C1—C2—C3—C1395.8 (3)C4—C3—C13—C1884.9 (2)
C11—C2—C3—C1381.7 (3)C18—C13—C14—C152.8 (3)
C2—C3—C4—C527.8 (3)C3—C13—C14—C15176.36 (19)
C13—C3—C4—C597.3 (3)C13—C14—C15—C161.9 (3)
C2—C3—C4—C19154.7 (2)C13—C14—C15—N2178.11 (19)
C13—C3—C4—C1980.1 (2)O6—N2—C15—C16176.5 (2)
C19—C4—C5—N1173.71 (19)O7—N2—C15—C162.1 (3)
C3—C4—C5—N18.9 (3)O6—N2—C15—C143.5 (3)
C19—C4—C5—C232.6 (4)O7—N2—C15—C14177.8 (2)
C3—C4—C5—C23174.8 (2)C14—C15—C16—C170.8 (4)
C1—N1—C5—C414.2 (3)N2—C15—C16—C17179.3 (2)
C6—N1—C5—C4154.1 (3)C15—C16—C17—C180.5 (4)
C1—N1—C5—C23162.4 (2)C14—C13—C18—C172.6 (3)
C6—N1—C5—C2329.2 (3)C3—C13—C18—C17176.5 (2)
C7—O1—C6—N190.3 (3)C16—C17—C18—C131.5 (4)
C1—N1—C6—O167.5 (3)C20—O9—C19—O80.0 (3)
C5—N1—C6—O1101.0 (3)C20—O9—C19—C4179.48 (18)
C6—O1—C7—C8178.2 (3)C5—C4—C19—O85.0 (4)
C10—O3—C9—O21.0 (4)C3—C4—C19—O8172.4 (2)
C10—O3—C9—C1178.8 (2)C5—C4—C19—O9175.5 (2)
C2—C1—C9—O2101.9 (4)C3—C4—C19—O97.0 (3)
N1—C1—C9—O272.6 (4)C19—O9—C20—C2282.1 (3)
C2—C1—C9—O380.3 (3)C19—O9—C20—C21156.7 (2)
 

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