organic compounds
Molecules of the title compound, C13H15NO6, are linked by two C—HO hydrogen bonds [HO = 2.32 and 2.46 Å, CO = 3.306 (2) and 3.393 (2) Å, and C—HO = 171 and 156°] into a C(4)C(7)[R32(11)] chain of rings.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027478/lh6149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027478/lh6149Isup2.hkl |
CCDC reference: 232148
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.125
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXS97; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
Diethyl 2-(4-nitrophenyl)malonate top
Crystal data top
C13H15NO6 | F(000) = 592 |
Mr = 281.26 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3150 reflections |
a = 11.9275 (6) Å | θ = 2.9–27.5° |
b = 13.8407 (8) Å | µ = 0.11 mm−1 |
c = 8.4595 (3) Å | T = 120 K |
β = 99.192 (3)° | Block, colourless |
V = 1378.60 (12) Å3 | 0.35 × 0.20 × 0.08 mm |
Z = 4 |
Data collection top
Nonius KappaCCD diffractometer | 3150 independent reflections |
Radiation source: rotating anode | 2007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
φ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SORTAV; Blessing 1995, 1997) | h = −12→15 |
Tmin = 0.967, Tmax = 0.991 | k = −17→17 |
14747 measured reflections | l = −10→8 |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.0884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3150 reflections | Δρmax = 0.30 e Å−3 |
184 parameters | Δρmin = −0.32 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: 0.023 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.26206 (15) | 0.70841 (13) | 0.0045 (2) | 0.0278 (4) | |
C2 | 0.31247 (15) | 0.78599 (13) | 0.0895 (2) | 0.0304 (4) | |
C3 | 0.42206 (15) | 0.77511 (13) | 0.1707 (2) | 0.0272 (4) | |
C4 | 0.47936 (14) | 0.68809 (12) | 0.16643 (19) | 0.0223 (4) | |
C5 | 0.42446 (15) | 0.61054 (13) | 0.0833 (2) | 0.0271 (4) | |
C6 | 0.31552 (15) | 0.62012 (13) | 0.0003 (2) | 0.0288 (4) | |
N1 | 0.14715 (14) | 0.71995 (13) | −0.0862 (2) | 0.0378 (4) | |
O11 | 0.10571 (12) | 0.65304 (12) | −0.1696 (2) | 0.0525 (4) | |
O12 | 0.09727 (13) | 0.79570 (13) | −0.0729 (2) | 0.0643 (5) | |
C7 | 0.60129 (14) | 0.68116 (12) | 0.24883 (19) | 0.0231 (4) | |
C8 | 0.62259 (14) | 0.59399 (13) | 0.3596 (2) | 0.0246 (4) | |
C9 | 0.68408 (14) | 0.67088 (12) | 0.1294 (2) | 0.0236 (4) | |
O81 | 0.63993 (11) | 0.62046 (9) | 0.51212 (14) | 0.0323 (3) | |
O82 | 0.62378 (12) | 0.51227 (9) | 0.31328 (15) | 0.0384 (4) | |
C81 | 0.66937 (19) | 0.54315 (15) | 0.6290 (2) | 0.0398 (5) | |
C82 | 0.7935 (2) | 0.52559 (17) | 0.6564 (3) | 0.0522 (6) | |
O91 | 0.78551 (10) | 0.70414 (9) | 0.19546 (14) | 0.0282 (3) | |
O92 | 0.66166 (10) | 0.63559 (9) | −0.00140 (13) | 0.0271 (3) | |
C91 | 0.87722 (15) | 0.69521 (14) | 0.0998 (2) | 0.0330 (5) | |
C92 | 0.92740 (18) | 0.59653 (16) | 0.1161 (3) | 0.0449 (5) | |
H2 | 0.2731 | 0.8455 | 0.0923 | 0.036* | |
H3 | 0.4585 | 0.8278 | 0.2299 | 0.033* | |
H5 | 0.4623 | 0.5501 | 0.0834 | 0.032* | |
H6 | 0.2784 | 0.5674 | −0.0582 | 0.035* | |
H7 | 0.6207 | 0.7411 | 0.3133 | 0.028* | |
H81A | 0.6291 | 0.4832 | 0.5894 | 0.048* | |
H81B | 0.6447 | 0.5612 | 0.7313 | 0.048* | |
H82A | 0.8177 | 0.5069 | 0.5553 | 0.078* | |
H82B | 0.8116 | 0.4736 | 0.7349 | 0.078* | |
H82C | 0.8333 | 0.5847 | 0.6971 | 0.078* | |
H91A | 0.9369 | 0.7437 | 0.1361 | 0.040* | |
H91B | 0.8470 | 0.7082 | −0.0141 | 0.040* | |
H92A | 0.9520 | 0.5819 | 0.2297 | 0.067* | |
H92B | 0.9929 | 0.5936 | 0.0595 | 0.067* | |
H92C | 0.8704 | 0.5492 | 0.0698 | 0.067* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0240 (9) | 0.0303 (10) | 0.0285 (9) | −0.0002 (8) | 0.0021 (7) | 0.0043 (8) |
C2 | 0.0304 (10) | 0.0221 (10) | 0.0390 (11) | 0.0035 (8) | 0.0066 (8) | 0.0012 (8) |
C3 | 0.0310 (10) | 0.0206 (9) | 0.0298 (10) | −0.0017 (7) | 0.0041 (7) | −0.0024 (7) |
C4 | 0.0273 (9) | 0.0212 (9) | 0.0191 (8) | 0.0002 (7) | 0.0055 (6) | 0.0016 (6) |
C5 | 0.0325 (10) | 0.0213 (9) | 0.0270 (9) | 0.0030 (8) | 0.0034 (7) | −0.0014 (7) |
C6 | 0.0311 (10) | 0.0249 (10) | 0.0294 (10) | −0.0038 (8) | 0.0020 (7) | −0.0026 (7) |
N1 | 0.0310 (9) | 0.0343 (10) | 0.0458 (10) | 0.0006 (8) | −0.0006 (7) | 0.0072 (8) |
O11 | 0.0390 (9) | 0.0486 (10) | 0.0629 (10) | −0.0046 (7) | −0.0128 (7) | −0.0064 (8) |
O12 | 0.0396 (9) | 0.0472 (11) | 0.0973 (14) | 0.0120 (8) | −0.0155 (8) | −0.0043 (9) |
C7 | 0.0279 (9) | 0.0197 (9) | 0.0211 (9) | 0.0001 (7) | 0.0018 (7) | −0.0022 (7) |
C8 | 0.0258 (10) | 0.0245 (10) | 0.0231 (9) | 0.0008 (7) | 0.0024 (7) | −0.0003 (7) |
C9 | 0.0268 (10) | 0.0189 (9) | 0.0236 (9) | 0.0009 (7) | −0.0004 (7) | 0.0029 (7) |
O81 | 0.0498 (8) | 0.0274 (7) | 0.0195 (6) | 0.0096 (6) | 0.0047 (5) | 0.0020 (5) |
O82 | 0.0604 (9) | 0.0224 (7) | 0.0290 (7) | 0.0011 (6) | −0.0027 (6) | 0.0000 (6) |
C81 | 0.0634 (14) | 0.0335 (11) | 0.0224 (10) | 0.0165 (10) | 0.0070 (9) | 0.0086 (8) |
C82 | 0.0610 (15) | 0.0388 (13) | 0.0491 (13) | 0.0059 (11) | −0.0152 (11) | 0.0073 (10) |
O91 | 0.0243 (7) | 0.0321 (7) | 0.0273 (7) | −0.0024 (5) | 0.0014 (5) | −0.0022 (5) |
O92 | 0.0315 (7) | 0.0280 (7) | 0.0213 (7) | −0.0005 (5) | 0.0025 (5) | −0.0025 (5) |
C91 | 0.0257 (10) | 0.0382 (12) | 0.0356 (11) | −0.0039 (8) | 0.0070 (7) | 0.0008 (8) |
C92 | 0.0352 (12) | 0.0402 (13) | 0.0599 (14) | 0.0032 (10) | 0.0098 (9) | −0.0047 (10) |
Geometric parameters (Å, º) top
C1—C2 | 1.376 (3) | C8—O81 | 1.325 (2) |
C1—C6 | 1.382 (3) | O81—C81 | 1.461 (2) |
C1—N1 | 1.469 (2) | C81—C82 | 1.482 (3) |
C2—C3 | 1.384 (3) | C81—H81A | 0.99 |
C2—H2 | 0.95 | C81—H81B | 0.99 |
C3—C4 | 1.388 (2) | C82—H82A | 0.98 |
C3—H3 | 0.95 | C82—H82B | 0.98 |
C4—C5 | 1.389 (2) | C82—H82C | 0.98 |
C4—C7 | 1.512 (2) | C9—O92 | 1.200 (2) |
C5—C6 | 1.381 (3) | C9—O91 | 1.331 (2) |
C5—H5 | 0.95 | O91—C91 | 1.466 (2) |
C6—H6 | 0.95 | C91—C92 | 1.489 (3) |
N1—O12 | 1.220 (2) | C91—H91A | 0.99 |
N1—O11 | 1.220 (2) | C91—H91B | 0.99 |
C7—C8 | 1.524 (2) | C92—H92A | 0.98 |
C7—C9 | 1.528 (2) | C92—H92B | 0.98 |
C7—H7 | 1.00 | C92—H92C | 0.98 |
C8—O82 | 1.198 (2) | ||
C2—C1—C6 | 122.62 (17) | C8—O81—C81 | 116.07 (14) |
C2—C1—N1 | 118.79 (16) | O81—C81—C82 | 110.62 (17) |
C6—C1—N1 | 118.59 (16) | O81—C81—H81A | 109.5 |
C1—C2—C3 | 118.26 (16) | C82—C81—H81A | 109.5 |
C1—C2—H2 | 120.9 | O81—C81—H81B | 109.5 |
C3—C2—H2 | 120.9 | C82—C81—H81B | 109.5 |
C2—C3—C4 | 120.76 (16) | H81A—C81—H81B | 108.1 |
C2—C3—H3 | 119.6 | C81—C82—H82A | 109.5 |
C4—C3—H3 | 119.6 | C81—C82—H82B | 109.5 |
C3—C4—C5 | 119.30 (16) | H82A—C82—H82B | 109.5 |
C3—C4—C7 | 118.97 (15) | C81—C82—H82C | 109.5 |
C5—C4—C7 | 121.70 (15) | H82A—C82—H82C | 109.5 |
C6—C5—C4 | 120.83 (16) | H82B—C82—H82C | 109.5 |
C6—C5—H5 | 119.6 | O92—C9—O91 | 125.55 (15) |
C4—C5—H5 | 119.6 | O92—C9—C7 | 125.12 (15) |
C5—C6—C1 | 118.18 (16) | O91—C9—C7 | 109.29 (13) |
C5—C6—H6 | 120.9 | C9—O91—C91 | 116.59 (13) |
C1—C6—H6 | 120.9 | O91—C91—C92 | 110.53 (15) |
O12—N1—O11 | 123.19 (17) | O91—C91—H91A | 109.5 |
O12—N1—C1 | 118.27 (17) | C92—C91—H91A | 109.5 |
O11—N1—C1 | 118.54 (17) | O91—C91—H91B | 109.5 |
C4—C7—C8 | 112.79 (14) | C92—C91—H91B | 109.5 |
C4—C7—C9 | 112.13 (13) | H91A—C91—H91B | 108.1 |
C8—C7—C9 | 105.72 (13) | C91—C92—H92A | 109.5 |
C4—C7—H7 | 108.7 | C91—C92—H92B | 109.5 |
C8—C7—H7 | 108.7 | H92A—C92—H92B | 109.5 |
C9—C7—H7 | 108.7 | C91—C92—H92C | 109.5 |
O82—C8—O81 | 124.86 (15) | H92A—C92—H92C | 109.5 |
O82—C8—C7 | 123.76 (15) | H92B—C92—H92C | 109.5 |
O81—C8—C7 | 111.38 (14) | ||
C6—C1—C2—C3 | 1.4 (3) | C3—C4—C7—C9 | −110.83 (17) |
N1—C1—C2—C3 | −178.11 (16) | C5—C4—C7—C9 | 67.4 (2) |
C1—C2—C3—C4 | −0.1 (3) | C4—C7—C8—O82 | 71.3 (2) |
C2—C3—C4—C5 | −1.8 (3) | C9—C7—C8—O82 | −51.5 (2) |
C2—C3—C4—C7 | 176.49 (15) | C4—C7—C8—O81 | −108.98 (16) |
C3—C4—C5—C6 | 2.4 (3) | C9—C7—C8—O81 | 128.15 (15) |
C7—C4—C5—C6 | −175.85 (16) | O82—C8—O81—C81 | 3.9 (3) |
C4—C5—C6—C1 | −1.1 (3) | C7—C8—O81—C81 | −175.76 (15) |
C2—C1—C6—C5 | −0.9 (3) | C8—O81—C81—C82 | 86.5 (2) |
N1—C1—C6—C5 | 178.67 (16) | C4—C7—C9—O92 | −27.5 (2) |
C2—C1—N1—O12 | −5.6 (3) | C8—C7—C9—O92 | 95.81 (19) |
C6—C1—N1—O12 | 174.88 (19) | C4—C7—C9—O91 | 154.61 (14) |
C2—C1—N1—O11 | 175.30 (17) | C8—C7—C9—O91 | −82.10 (16) |
C6—C1—N1—O11 | −4.3 (3) | O92—C9—O91—C91 | −0.9 (2) |
C3—C4—C7—C8 | 129.95 (16) | C7—C9—O91—C91 | 176.99 (13) |
C5—C4—C7—C8 | −51.8 (2) | C9—O91—C91—C92 | −82.42 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O92i | 1.00 | 2.32 | 3.306 (2) | 171 |
C81—H81B···O92ii | 0.99 | 2.46 | 3.393 (2) | 156 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1. |