organic compounds
The crystal structure of the title compound, C18H17N3O6, is formed by single molecules linked by N—HO 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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021020/cm6058sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021020/cm6058Isup2.hkl |
CCDC reference: 225860
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
C18H17N3O6 | Z = 2 |
Mr = 371.35 | F(000) = 388 |
Triclinic, P1 | Dx = 1.451 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.555 (3) Å | Cell parameters from 25 reflections |
b = 9.445 (2) Å | θ = 6.8–19.3° |
c = 11.322 (4) Å | µ = 0.11 mm−1 |
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 tube | θmax = 28.0°, θmin = 1.9° |
Graphite monochromator | h = 0→11 |
θ/2θ scans | k = −12→12 |
4128 measured reflections | l = −13→14 |
4128 independent reflections | 2 standard reflections every 100 min |
1439 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H-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 reflections | Δρmax = 0.18 e Å−3 |
248 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0111 (6) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O31 | 0.7852 (3) | 0.47354 (19) | 0.57144 (17) | 0.0627 (7) | |
O32 | 0.8935 (2) | 0.32963 (17) | 0.70457 (16) | 0.0436 (5) | |
O41 | 0.5892 (3) | 0.1351 (2) | 1.22031 (17) | 0.0681 (7) | |
O42 | 0.8341 (3) | 0.0584 (3) | 1.1124 (2) | 0.1105 (11) | |
O5 | 0.8806 (2) | −0.21698 (18) | 0.73356 (16) | 0.0460 (6) | |
O7 | 0.6814 (3) | −0.17335 (19) | 0.39741 (17) | 0.0561 (6) | |
N1 | 0.7148 (3) | 0.1096 (2) | 0.44099 (18) | 0.0407 (7) | |
H1 | 0.6782 | 0.1093 | 0.3782 | 0.049* | |
N41 | 0.6905 (4) | 0.1058 (3) | 1.1217 (2) | 0.0556 (8) | |
N6 | 0.7846 (3) | −0.2351 (2) | 0.56719 (19) | 0.0437 (7) | |
H6 | 0.7905 | −0.3275 | 0.5721 | 0.052* | |
C2 | 0.7403 (3) | 0.2307 (3) | 0.4757 (2) | 0.0373 (8) | |
C3 | 0.7937 (3) | 0.2306 (2) | 0.5751 (2) | 0.0301 (7) | |
C4 | 0.8223 (3) | 0.1022 (2) | 0.6638 (2) | 0.0300 (7) | |
H4 | 0.9367 | 0.0856 | 0.6702 | 0.036* | |
C5 | 0.8284 (4) | −0.1637 (3) | 0.6489 (2) | 0.0364 (8) | |
C7 | 0.7319 (4) | −0.1474 (3) | 0.4795 (3) | 0.0393 (8) | |
C9 | 0.8012 (3) | −0.0177 (3) | 0.6060 (2) | 0.0303 (7) | |
C8 | 0.7487 (3) | −0.0091 (3) | 0.5077 (2) | 0.0313 (7) | |
C22 | 0.7038 (4) | 0.3505 (3) | 0.3902 (2) | 0.0530 (9) | |
H22A | 0.7160 | 0.4388 | 0.4181 | 0.079* | |
H22B | 0.5912 | 0.3601 | 0.3866 | 0.079* | |
H22C | 0.7800 | 0.3319 | 0.3092 | 0.079* | |
C31 | 0.8209 (4) | 0.3580 (3) | 0.6132 (2) | 0.0426 (8) | |
C32 | 0.9057 (4) | 0.4451 (3) | 0.7696 (3) | 0.0524 (9) | |
H32 | 0.9341 | 0.5264 | 0.7113 | 0.063* | |
C33 | 0.7395 (4) | 0.4918 (3) | 0.8609 (3) | 0.0810 (12) | |
H33A | 0.6567 | 0.5274 | 0.8176 | 0.122* | |
H33B | 0.7450 | 0.5677 | 0.9086 | 0.122* | |
H33C | 0.7098 | 0.4106 | 0.9152 | 0.122* | |
C34 | 1.0421 (4) | 0.3875 (3) | 0.8290 (3) | 0.0759 (11) | |
H34A | 1.0141 | 0.3073 | 0.8854 | 0.114* | |
H34B | 1.0554 | 0.4628 | 0.8735 | 0.114* | |
H34C | 1.1448 | 0.3552 | 0.7663 | 0.114* | |
C41 | 0.6984 (4) | 0.1246 (2) | 0.7912 (2) | 0.0290 (7) | |
C42 | 0.7518 (3) | 0.1009 (2) | 0.8964 (2) | 0.0360 (7) | |
H42 | 0.8645 | 0.0677 | 0.8907 | 0.043* | |
C43 | 0.6365 (4) | 0.1271 (3) | 1.0091 (2) | 0.0345 (7) | |
C44 | 0.4705 (4) | 0.1738 (3) | 1.0237 (2) | 0.0411 (8) | |
H44 | 0.3956 | 0.1911 | 1.1018 | 0.049* | |
C45 | 0.4167 (4) | 0.1946 (3) | 0.9194 (2) | 0.0433 (8) | |
H45 | 0.3034 | 0.2257 | 0.9264 | 0.052* | |
C46 | 0.5303 (4) | 0.1696 (3) | 0.8035 (2) | 0.0385 (8) | |
H46 | 0.4924 | 0.1835 | 0.7335 | 0.046* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O31 | 0.110 (2) | 0.0245 (11) | 0.0714 (14) | −0.0181 (13) | −0.0536 (14) | 0.0093 (10) |
O32 | 0.0652 (16) | 0.0240 (10) | 0.0498 (12) | −0.0081 (10) | −0.0280 (12) | −0.0045 (9) |
O41 | 0.089 (2) | 0.0831 (16) | 0.0288 (11) | −0.0126 (14) | −0.0127 (13) | −0.0100 (11) |
O42 | 0.067 (2) | 0.206 (3) | 0.0508 (16) | 0.013 (2) | −0.0326 (16) | −0.0150 (16) |
O5 | 0.0680 (16) | 0.0309 (11) | 0.0389 (11) | −0.0026 (11) | −0.0214 (11) | 0.0011 (9) |
O7 | 0.0752 (17) | 0.0457 (13) | 0.0590 (13) | −0.0103 (11) | −0.0327 (13) | −0.0167 (10) |
N1 | 0.0563 (19) | 0.0375 (14) | 0.0321 (13) | −0.0056 (13) | −0.0205 (13) | −0.0030 (11) |
N41 | 0.066 (2) | 0.0636 (19) | 0.0379 (17) | −0.0117 (18) | −0.0163 (18) | −0.0034 (14) |
N6 | 0.069 (2) | 0.0224 (13) | 0.0443 (15) | −0.0111 (13) | −0.0198 (14) | −0.0062 (11) |
C2 | 0.046 (2) | 0.0287 (16) | 0.0343 (16) | −0.0067 (16) | −0.0084 (16) | 0.0000 (13) |
C3 | 0.041 (2) | 0.0223 (15) | 0.0283 (15) | −0.0078 (14) | −0.0114 (15) | 0.0006 (12) |
C4 | 0.0363 (19) | 0.0259 (15) | 0.0283 (14) | −0.0054 (14) | −0.0105 (14) | −0.0016 (12) |
C5 | 0.046 (2) | 0.0324 (17) | 0.0289 (15) | −0.0071 (15) | −0.0078 (16) | −0.0035 (14) |
C7 | 0.039 (2) | 0.0374 (18) | 0.0405 (18) | −0.0105 (16) | −0.0047 (17) | −0.0121 (15) |
C9 | 0.041 (2) | 0.0225 (15) | 0.0265 (14) | −0.0085 (14) | −0.0063 (15) | −0.0017 (12) |
C8 | 0.039 (2) | 0.0263 (15) | 0.0277 (15) | −0.0063 (15) | −0.0058 (15) | −0.0059 (12) |
C22 | 0.072 (3) | 0.0405 (18) | 0.0452 (18) | −0.0059 (18) | −0.0228 (18) | 0.0097 (14) |
C31 | 0.051 (2) | 0.0364 (19) | 0.0411 (18) | −0.0094 (18) | −0.0133 (17) | −0.0038 (15) |
C32 | 0.082 (3) | 0.0252 (16) | 0.058 (2) | −0.0132 (18) | −0.028 (2) | −0.0066 (15) |
C33 | 0.107 (3) | 0.049 (2) | 0.080 (2) | −0.006 (2) | −0.014 (2) | −0.0283 (18) |
C34 | 0.110 (3) | 0.059 (2) | 0.082 (2) | −0.016 (2) | −0.060 (2) | −0.0111 (18) |
C41 | 0.038 (2) | 0.0210 (14) | 0.0299 (16) | −0.0067 (14) | −0.0112 (15) | −0.0020 (11) |
C42 | 0.037 (2) | 0.0353 (16) | 0.0358 (17) | −0.0036 (14) | −0.0113 (16) | −0.0065 (13) |
C43 | 0.042 (2) | 0.0360 (16) | 0.0298 (16) | −0.0075 (16) | −0.0172 (17) | −0.0029 (13) |
C44 | 0.059 (3) | 0.0306 (16) | 0.0303 (17) | −0.0065 (17) | −0.0081 (17) | −0.0057 (13) |
C45 | 0.040 (2) | 0.0440 (19) | 0.0446 (18) | −0.0017 (16) | −0.0131 (17) | −0.0052 (14) |
C46 | 0.049 (2) | 0.0398 (17) | 0.0272 (16) | −0.0060 (16) | −0.0134 (16) | −0.0018 (13) |
Geometric parameters (Å, º) top
O31—C31 | 1.155 (3) | C9—C8 | 1.309 (3) |
O32—C31 | 1.334 (3) | C22—H22A | 0.9600 |
O32—C32 | 1.418 (3) | C22—H22B | 0.9600 |
O41—N41 | 1.205 (3) | C22—H22C | 0.9600 |
O42—N41 | 1.187 (3) | C32—C33 | 1.491 (4) |
O5—C5 | 1.193 (3) | C32—C34 | 1.491 (4) |
O7—C7 | 1.203 (3) | C32—H32 | 0.9800 |
N1—C8 | 1.309 (3) | C33—H33A | 0.9600 |
N1—C2 | 1.331 (3) | C33—H33B | 0.9600 |
N1—H1 | 0.8600 | C33—H33C | 0.9600 |
N41—C43 | 1.462 (3) | C34—H34A | 0.9600 |
N6—C7 | 1.341 (3) | C34—H34B | 0.9600 |
N6—C5 | 1.382 (3) | C34—H34C | 0.9600 |
N6—H6 | 0.8600 | C41—C46 | 1.374 (3) |
C2—C3 | 1.335 (3) | C41—C42 | 1.379 (3) |
C2—C22 | 1.450 (3) | C42—C43 | 1.366 (3) |
C3—C31 | 1.409 (3) | C42—H42 | 0.9300 |
C3—C4 | 1.513 (3) | C43—C44 | 1.355 (3) |
C4—C9 | 1.438 (3) | C44—C45 | 1.371 (3) |
C4—C41 | 1.515 (3) | C44—H44 | 0.9300 |
C4—H4 | 0.9800 | C45—C46 | 1.386 (3) |
C5—C9 | 1.404 (3) | C45—H45 | 0.9300 |
C7—C8 | 1.425 (3) | C46—H46 | 0.9300 |
C31—O32—C32 | 120.1 (2) | O31—C31—O32 | 123.4 (3) |
C8—N1—C2 | 116.4 (2) | O31—C31—C3 | 124.8 (3) |
C8—N1—H1 | 121.8 | O32—C31—C3 | 111.7 (2) |
C2—N1—H1 | 121.8 | O32—C32—C33 | 107.5 (3) |
O42—N41—O41 | 122.2 (3) | O32—C32—C34 | 106.7 (2) |
O42—N41—C43 | 118.1 (3) | C33—C32—C34 | 113.1 (3) |
O41—N41—C43 | 119.6 (3) | O32—C32—H32 | 109.8 |
C7—N6—C5 | 114.0 (2) | C33—C32—H32 | 109.8 |
C7—N6—H6 | 123.0 | C34—C32—H32 | 109.8 |
C5—N6—H6 | 123.0 | C32—C33—H33A | 109.5 |
N1—C2—C3 | 121.3 (2) | C32—C33—H33B | 109.5 |
N1—C2—C22 | 109.6 (2) | H33A—C33—H33B | 109.5 |
C3—C2—C22 | 129.0 (3) | C32—C33—H33C | 109.5 |
C2—C3—C31 | 122.0 (2) | H33A—C33—H33C | 109.5 |
C2—C3—C4 | 126.2 (2) | H33B—C33—H33C | 109.5 |
C31—C3—C4 | 111.8 (2) | C32—C34—H34A | 109.5 |
C9—C4—C3 | 103.8 (2) | C32—C34—H34B | 109.5 |
C9—C4—C41 | 111.5 (2) | H34A—C34—H34B | 109.5 |
C3—C4—C41 | 111.7 (2) | C32—C34—H34C | 109.5 |
C9—C4—H4 | 109.9 | H34A—C34—H34C | 109.5 |
C3—C4—H4 | 109.9 | H34B—C34—H34C | 109.5 |
C41—C4—H4 | 109.9 | C46—C41—C42 | 118.8 (3) |
O5—C5—N6 | 127.0 (2) | C46—C41—C4 | 120.3 (2) |
O5—C5—C9 | 129.4 (3) | C42—C41—C4 | 120.8 (3) |
N6—C5—C9 | 103.6 (2) | C43—C42—C41 | 118.9 (3) |
O7—C7—N6 | 130.9 (3) | C43—C42—H42 | 120.5 |
O7—C7—C8 | 127.1 (3) | C41—C42—H42 | 120.5 |
N6—C7—C8 | 102.0 (2) | C44—C43—C42 | 123.4 (3) |
C8—C9—C5 | 108.7 (2) | C44—C43—N41 | 116.6 (3) |
C8—C9—C4 | 126.0 (2) | C42—C43—N41 | 120.0 (3) |
C5—C9—C4 | 125.2 (2) | C43—C44—C45 | 117.8 (3) |
C9—C8—N1 | 125.8 (2) | C43—C44—H44 | 121.1 |
C9—C8—C7 | 111.6 (3) | C45—C44—H44 | 121.1 |
N1—C8—C7 | 122.6 (2) | C44—C45—C46 | 120.4 (3) |
C2—C22—H22A | 109.5 | C44—C45—H45 | 119.8 |
C2—C22—H22B | 109.5 | C46—C45—H45 | 119.8 |
H22A—C22—H22B | 109.5 | C41—C46—C45 | 120.7 (3) |
C2—C22—H22C | 109.5 | C41—C46—H46 | 119.7 |
H22A—C22—H22C | 109.5 | C45—C46—H46 | 119.7 |
H22B—C22—H22C | 109.5 | ||
C8—N1—C2—C3 | −1.5 (4) | N6—C7—C8—C9 | −2.0 (3) |
C8—N1—C2—C22 | 177.7 (3) | O7—C7—C8—N1 | −2.7 (5) |
N1—C2—C3—C31 | −179.9 (3) | N6—C7—C8—N1 | 177.8 (3) |
C22—C2—C3—C31 | 1.0 (5) | C32—O32—C31—O31 | 10.5 (5) |
N1—C2—C3—C4 | −3.7 (4) | C32—O32—C31—C3 | −169.4 (2) |
C22—C2—C3—C4 | 177.2 (3) | C2—C3—C31—O31 | 8.0 (5) |
C2—C3—C4—C9 | 7.6 (4) | C4—C3—C31—O31 | −168.7 (3) |
C31—C3—C4—C9 | −175.9 (2) | C2—C3—C31—O32 | −172.2 (3) |
C2—C3—C4—C41 | −112.6 (3) | C4—C3—C31—O32 | 11.2 (3) |
C31—C3—C4—C41 | 63.9 (3) | C31—O32—C32—C33 | 78.9 (3) |
C7—N6—C5—O5 | −179.0 (3) | C31—O32—C32—C34 | −159.5 (2) |
C7—N6—C5—C9 | −0.6 (3) | C9—C4—C41—C46 | −66.9 (3) |
C5—N6—C7—O7 | −177.9 (3) | C3—C4—C41—C46 | 48.7 (3) |
C5—N6—C7—C8 | 1.5 (3) | C9—C4—C41—C42 | 113.4 (3) |
O5—C5—C9—C8 | 177.6 (3) | C3—C4—C41—C42 | −131.0 (2) |
N6—C5—C9—C8 | −0.7 (3) | C46—C41—C42—C43 | −1.9 (4) |
O5—C5—C9—C4 | −4.4 (5) | C4—C41—C42—C43 | 177.8 (2) |
N6—C5—C9—C4 | 177.2 (2) | C41—C42—C43—C44 | 0.9 (4) |
C3—C4—C9—C8 | −7.6 (4) | C41—C42—C43—N41 | −178.7 (2) |
C41—C4—C9—C8 | 112.8 (3) | O42—N41—C43—C44 | 176.4 (3) |
C3—C4—C9—C5 | 174.8 (3) | O41—N41—C43—C44 | −2.8 (4) |
C41—C4—C9—C5 | −64.8 (4) | O42—N41—C43—C42 | −3.9 (4) |
C5—C9—C8—N1 | −178.1 (3) | O41—N41—C43—C42 | 176.8 (3) |
C4—C9—C8—N1 | 4.0 (5) | C42—C43—C44—C45 | 0.4 (4) |
C5—C9—C8—C7 | 1.7 (3) | N41—C43—C44—C45 | 180.0 (2) |
C4—C9—C8—C7 | −176.2 (3) | C43—C44—C45—C46 | −0.6 (4) |
C2—N1—C8—C9 | 1.6 (4) | C42—C41—C46—C45 | 1.7 (4) |
C2—N1—C8—C7 | −178.2 (3) | C4—C41—C46—C45 | −178.0 (2) |
O7—C7—C8—C9 | 177.4 (3) | C44—C45—C46—C41 | −0.4 (4) |