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The crystal structure of the title compound, C18H17N3O6, is formed by single mol­ecules linked by N—H...O hydrogen bonds into planar sheets. The dihedral angle between the mean planes of the pyridine and substituted phenyl rings is 84.2 (1)°. The 3-nitro substituent on the phenyl ring is rotated from coplanarity with the ring by only 3.7 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021020/cm6058sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021020/cm6058Isup2.hkl
Contains datablock I

CCDC reference: 225860

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.083
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc. PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT230_ALERT_2_B Hirshfeld Test Diff for C43 - C44 = 7.42 su
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.53 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.39 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O31 - C31 = 5.96 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N41 - C43 = 6.89 su PLAT432_ALERT_2_C Short Inter X...Y Contact C43 .. C45 = 3.15 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Syntex P21 Diffractometer Control Software (Syntex, 1973; cell refinement: Syntex P21 Diffractometer Control 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.

isopropyl 2-methyl-4-(3-nitrophenyl)-5,7-dioxo-4,5,6,7-tetrahydro-1H- pyrrolo[3,4-b]pyridine-3-carboxylate top
Crystal data top
C18H17N3O6Z = 2
Mr = 371.35F(000) = 388
Triclinic, P1Dx = 1.451 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.555 (3) ÅCell parameters from 25 reflections
b = 9.445 (2) Åθ = 6.8–19.3°
c = 11.322 (4) ŵ = 0.11 mm1
α = 83.76 (2)°T = 293 K
β = 72.52 (3)°Prism, yellow
γ = 77.18 (2)°0.4 × 0.3 × 0.3 mm
V = 850.0 (5) Å3
Data collection top
Syntex P21
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 28.0°, θmin = 1.9°
Graphite monochromatorh = 011
θ/2θ scansk = 1212
4128 measured reflectionsl = 1314
4128 independent reflections2 standard reflections every 100 min
1439 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)] = 0.060H-atom parameters constrained
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0121P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.001
4128 reflectionsΔρmax = 0.18 e Å3
248 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0111 (6)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O310.7852 (3)0.47354 (19)0.57144 (17)0.0627 (7)
O320.8935 (2)0.32963 (17)0.70457 (16)0.0436 (5)
O410.5892 (3)0.1351 (2)1.22031 (17)0.0681 (7)
O420.8341 (3)0.0584 (3)1.1124 (2)0.1105 (11)
O50.8806 (2)0.21698 (18)0.73356 (16)0.0460 (6)
O70.6814 (3)0.17335 (19)0.39741 (17)0.0561 (6)
N10.7148 (3)0.1096 (2)0.44099 (18)0.0407 (7)
H10.67820.10930.37820.049*
N410.6905 (4)0.1058 (3)1.1217 (2)0.0556 (8)
N60.7846 (3)0.2351 (2)0.56719 (19)0.0437 (7)
H60.79050.32750.57210.052*
C20.7403 (3)0.2307 (3)0.4757 (2)0.0373 (8)
C30.7937 (3)0.2306 (2)0.5751 (2)0.0301 (7)
C40.8223 (3)0.1022 (2)0.6638 (2)0.0300 (7)
H40.93670.08560.67020.036*
C50.8284 (4)0.1637 (3)0.6489 (2)0.0364 (8)
C70.7319 (4)0.1474 (3)0.4795 (3)0.0393 (8)
C90.8012 (3)0.0177 (3)0.6060 (2)0.0303 (7)
C80.7487 (3)0.0091 (3)0.5077 (2)0.0313 (7)
C220.7038 (4)0.3505 (3)0.3902 (2)0.0530 (9)
H22A0.71600.43880.41810.079*
H22B0.59120.36010.38660.079*
H22C0.78000.33190.30920.079*
C310.8209 (4)0.3580 (3)0.6132 (2)0.0426 (8)
C320.9057 (4)0.4451 (3)0.7696 (3)0.0524 (9)
H320.93410.52640.71130.063*
C330.7395 (4)0.4918 (3)0.8609 (3)0.0810 (12)
H33A0.65670.52740.81760.122*
H33B0.74500.56770.90860.122*
H33C0.70980.41060.91520.122*
C341.0421 (4)0.3875 (3)0.8290 (3)0.0759 (11)
H34A1.01410.30730.88540.114*
H34B1.05540.46280.87350.114*
H34C1.14480.35520.76630.114*
C410.6984 (4)0.1246 (2)0.7912 (2)0.0290 (7)
C420.7518 (3)0.1009 (2)0.8964 (2)0.0360 (7)
H420.86450.06770.89070.043*
C430.6365 (4)0.1271 (3)1.0091 (2)0.0345 (7)
C440.4705 (4)0.1738 (3)1.0237 (2)0.0411 (8)
H440.39560.19111.10180.049*
C450.4167 (4)0.1946 (3)0.9194 (2)0.0433 (8)
H450.30340.22570.92640.052*
C460.5303 (4)0.1696 (3)0.8035 (2)0.0385 (8)
H460.49240.18350.73350.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.110 (2)0.0245 (11)0.0714 (14)0.0181 (13)0.0536 (14)0.0093 (10)
O320.0652 (16)0.0240 (10)0.0498 (12)0.0081 (10)0.0280 (12)0.0045 (9)
O410.089 (2)0.0831 (16)0.0288 (11)0.0126 (14)0.0127 (13)0.0100 (11)
O420.067 (2)0.206 (3)0.0508 (16)0.013 (2)0.0326 (16)0.0150 (16)
O50.0680 (16)0.0309 (11)0.0389 (11)0.0026 (11)0.0214 (11)0.0011 (9)
O70.0752 (17)0.0457 (13)0.0590 (13)0.0103 (11)0.0327 (13)0.0167 (10)
N10.0563 (19)0.0375 (14)0.0321 (13)0.0056 (13)0.0205 (13)0.0030 (11)
N410.066 (2)0.0636 (19)0.0379 (17)0.0117 (18)0.0163 (18)0.0034 (14)
N60.069 (2)0.0224 (13)0.0443 (15)0.0111 (13)0.0198 (14)0.0062 (11)
C20.046 (2)0.0287 (16)0.0343 (16)0.0067 (16)0.0084 (16)0.0000 (13)
C30.041 (2)0.0223 (15)0.0283 (15)0.0078 (14)0.0114 (15)0.0006 (12)
C40.0363 (19)0.0259 (15)0.0283 (14)0.0054 (14)0.0105 (14)0.0016 (12)
C50.046 (2)0.0324 (17)0.0289 (15)0.0071 (15)0.0078 (16)0.0035 (14)
C70.039 (2)0.0374 (18)0.0405 (18)0.0105 (16)0.0047 (17)0.0121 (15)
C90.041 (2)0.0225 (15)0.0265 (14)0.0085 (14)0.0063 (15)0.0017 (12)
C80.039 (2)0.0263 (15)0.0277 (15)0.0063 (15)0.0058 (15)0.0059 (12)
C220.072 (3)0.0405 (18)0.0452 (18)0.0059 (18)0.0228 (18)0.0097 (14)
C310.051 (2)0.0364 (19)0.0411 (18)0.0094 (18)0.0133 (17)0.0038 (15)
C320.082 (3)0.0252 (16)0.058 (2)0.0132 (18)0.028 (2)0.0066 (15)
C330.107 (3)0.049 (2)0.080 (2)0.006 (2)0.014 (2)0.0283 (18)
C340.110 (3)0.059 (2)0.082 (2)0.016 (2)0.060 (2)0.0111 (18)
C410.038 (2)0.0210 (14)0.0299 (16)0.0067 (14)0.0112 (15)0.0020 (11)
C420.037 (2)0.0353 (16)0.0358 (17)0.0036 (14)0.0113 (16)0.0065 (13)
C430.042 (2)0.0360 (16)0.0298 (16)0.0075 (16)0.0172 (17)0.0029 (13)
C440.059 (3)0.0306 (16)0.0303 (17)0.0065 (17)0.0081 (17)0.0057 (13)
C450.040 (2)0.0440 (19)0.0446 (18)0.0017 (16)0.0131 (17)0.0052 (14)
C460.049 (2)0.0398 (17)0.0272 (16)0.0060 (16)0.0134 (16)0.0018 (13)
Geometric parameters (Å, º) top
O31—C311.155 (3)C9—C81.309 (3)
O32—C311.334 (3)C22—H22A0.9600
O32—C321.418 (3)C22—H22B0.9600
O41—N411.205 (3)C22—H22C0.9600
O42—N411.187 (3)C32—C331.491 (4)
O5—C51.193 (3)C32—C341.491 (4)
O7—C71.203 (3)C32—H320.9800
N1—C81.309 (3)C33—H33A0.9600
N1—C21.331 (3)C33—H33B0.9600
N1—H10.8600C33—H33C0.9600
N41—C431.462 (3)C34—H34A0.9600
N6—C71.341 (3)C34—H34B0.9600
N6—C51.382 (3)C34—H34C0.9600
N6—H60.8600C41—C461.374 (3)
C2—C31.335 (3)C41—C421.379 (3)
C2—C221.450 (3)C42—C431.366 (3)
C3—C311.409 (3)C42—H420.9300
C3—C41.513 (3)C43—C441.355 (3)
C4—C91.438 (3)C44—C451.371 (3)
C4—C411.515 (3)C44—H440.9300
C4—H40.9800C45—C461.386 (3)
C5—C91.404 (3)C45—H450.9300
C7—C81.425 (3)C46—H460.9300
C31—O32—C32120.1 (2)O31—C31—O32123.4 (3)
C8—N1—C2116.4 (2)O31—C31—C3124.8 (3)
C8—N1—H1121.8O32—C31—C3111.7 (2)
C2—N1—H1121.8O32—C32—C33107.5 (3)
O42—N41—O41122.2 (3)O32—C32—C34106.7 (2)
O42—N41—C43118.1 (3)C33—C32—C34113.1 (3)
O41—N41—C43119.6 (3)O32—C32—H32109.8
C7—N6—C5114.0 (2)C33—C32—H32109.8
C7—N6—H6123.0C34—C32—H32109.8
C5—N6—H6123.0C32—C33—H33A109.5
N1—C2—C3121.3 (2)C32—C33—H33B109.5
N1—C2—C22109.6 (2)H33A—C33—H33B109.5
C3—C2—C22129.0 (3)C32—C33—H33C109.5
C2—C3—C31122.0 (2)H33A—C33—H33C109.5
C2—C3—C4126.2 (2)H33B—C33—H33C109.5
C31—C3—C4111.8 (2)C32—C34—H34A109.5
C9—C4—C3103.8 (2)C32—C34—H34B109.5
C9—C4—C41111.5 (2)H34A—C34—H34B109.5
C3—C4—C41111.7 (2)C32—C34—H34C109.5
C9—C4—H4109.9H34A—C34—H34C109.5
C3—C4—H4109.9H34B—C34—H34C109.5
C41—C4—H4109.9C46—C41—C42118.8 (3)
O5—C5—N6127.0 (2)C46—C41—C4120.3 (2)
O5—C5—C9129.4 (3)C42—C41—C4120.8 (3)
N6—C5—C9103.6 (2)C43—C42—C41118.9 (3)
O7—C7—N6130.9 (3)C43—C42—H42120.5
O7—C7—C8127.1 (3)C41—C42—H42120.5
N6—C7—C8102.0 (2)C44—C43—C42123.4 (3)
C8—C9—C5108.7 (2)C44—C43—N41116.6 (3)
C8—C9—C4126.0 (2)C42—C43—N41120.0 (3)
C5—C9—C4125.2 (2)C43—C44—C45117.8 (3)
C9—C8—N1125.8 (2)C43—C44—H44121.1
C9—C8—C7111.6 (3)C45—C44—H44121.1
N1—C8—C7122.6 (2)C44—C45—C46120.4 (3)
C2—C22—H22A109.5C44—C45—H45119.8
C2—C22—H22B109.5C46—C45—H45119.8
H22A—C22—H22B109.5C41—C46—C45120.7 (3)
C2—C22—H22C109.5C41—C46—H46119.7
H22A—C22—H22C109.5C45—C46—H46119.7
H22B—C22—H22C109.5
C8—N1—C2—C31.5 (4)N6—C7—C8—C92.0 (3)
C8—N1—C2—C22177.7 (3)O7—C7—C8—N12.7 (5)
N1—C2—C3—C31179.9 (3)N6—C7—C8—N1177.8 (3)
C22—C2—C3—C311.0 (5)C32—O32—C31—O3110.5 (5)
N1—C2—C3—C43.7 (4)C32—O32—C31—C3169.4 (2)
C22—C2—C3—C4177.2 (3)C2—C3—C31—O318.0 (5)
C2—C3—C4—C97.6 (4)C4—C3—C31—O31168.7 (3)
C31—C3—C4—C9175.9 (2)C2—C3—C31—O32172.2 (3)
C2—C3—C4—C41112.6 (3)C4—C3—C31—O3211.2 (3)
C31—C3—C4—C4163.9 (3)C31—O32—C32—C3378.9 (3)
C7—N6—C5—O5179.0 (3)C31—O32—C32—C34159.5 (2)
C7—N6—C5—C90.6 (3)C9—C4—C41—C4666.9 (3)
C5—N6—C7—O7177.9 (3)C3—C4—C41—C4648.7 (3)
C5—N6—C7—C81.5 (3)C9—C4—C41—C42113.4 (3)
O5—C5—C9—C8177.6 (3)C3—C4—C41—C42131.0 (2)
N6—C5—C9—C80.7 (3)C46—C41—C42—C431.9 (4)
O5—C5—C9—C44.4 (5)C4—C41—C42—C43177.8 (2)
N6—C5—C9—C4177.2 (2)C41—C42—C43—C440.9 (4)
C3—C4—C9—C87.6 (4)C41—C42—C43—N41178.7 (2)
C41—C4—C9—C8112.8 (3)O42—N41—C43—C44176.4 (3)
C3—C4—C9—C5174.8 (3)O41—N41—C43—C442.8 (4)
C41—C4—C9—C564.8 (4)O42—N41—C43—C423.9 (4)
C5—C9—C8—N1178.1 (3)O41—N41—C43—C42176.8 (3)
C4—C9—C8—N14.0 (5)C42—C43—C44—C450.4 (4)
C5—C9—C8—C71.7 (3)N41—C43—C44—C45180.0 (2)
C4—C9—C8—C7176.2 (3)C43—C44—C45—C460.6 (4)
C2—N1—C8—C91.6 (4)C42—C41—C46—C451.7 (4)
C2—N1—C8—C7178.2 (3)C4—C41—C46—C45178.0 (2)
O7—C7—C8—C9177.4 (3)C44—C45—C46—C410.4 (4)
 

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