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In the crystal structure of the title compound, C
11H
13NO
4, the asymmetric unit contains only one half-molecule; the molecule lies on a twofold rotation axis. The crystal structure is stabilized by intermolecular C—H
O and C—H
N hydrogen bonds, linking the molecules along the
b axis.
Supporting information
CCDC reference: 618229
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.049
- wR factor = 0.168
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Diethyl pyridine-2,6-dicarboxylate
top
Crystal data top
C11H13NO4 | F(000) = 472 |
Mr = 223.22 | Dx = 1.243 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 15.222 (3) Å | θ = 10–13° |
b = 6.3480 (13) Å | µ = 0.10 mm−1 |
c = 12.423 (3) Å | T = 296 K |
β = 96.45 (3)° | Block, colourless |
V = 1192.8 (5) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 799 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
ω/2θ scans | h = −18→18 |
Absorption correction: ψ scan (North et al., 1968) | k = −7→0 |
Tmin = 0.964, Tmax = 0.982 | l = −15→0 |
1226 measured reflections | 3 standard reflections every 120 min |
1166 independent reflections | 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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1166 reflections | Δρmax = 0.22 e Å−3 |
75 parameters | Δρmin = −0.17 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: 0.019 (5) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.12757 (9) | 0.0924 (2) | 0.50020 (10) | 0.0622 (5) | |
O2 | 0.10242 (11) | −0.2140 (2) | 0.41701 (12) | 0.0835 (7) | |
N | 0.0000 | −0.0085 (3) | 0.2500 | 0.0434 (6) | |
C1 | 0.21009 (14) | 0.1613 (4) | 0.66866 (16) | 0.0718 (7) | |
H1A | 0.2481 | 0.1031 | 0.7282 | 0.108* | |
H1B | 0.1582 | 0.2190 | 0.6948 | 0.108* | |
H1C | 0.2409 | 0.2705 | 0.6349 | 0.108* | |
C2 | 0.18379 (14) | −0.0082 (3) | 0.58780 (15) | 0.0619 (6) | |
H2A | 0.2356 | −0.0691 | 0.5610 | 0.074* | |
H2B | 0.1518 | −0.1191 | 0.6204 | 0.074* | |
C3 | 0.09233 (11) | −0.0276 (3) | 0.42010 (14) | 0.0477 (6) | |
C4 | 0.04241 (10) | 0.1019 (3) | 0.33192 (13) | 0.0439 (5) | |
C5 | 0.04282 (11) | 0.3218 (3) | 0.33600 (16) | 0.0555 (6) | |
H5A | 0.0714 | 0.3924 | 0.3955 | 0.067* | |
C6 | 0.0000 | 0.4319 (4) | 0.2500 | 0.0619 (8) | |
H6A | 0.0000 | 0.5784 | 0.2500 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0760 (10) | 0.0434 (8) | 0.0607 (9) | 0.0065 (7) | −0.0211 (7) | −0.0067 (6) |
O2 | 0.1225 (14) | 0.0346 (9) | 0.0813 (11) | 0.0063 (8) | −0.0410 (10) | −0.0021 (7) |
N | 0.0470 (11) | 0.0272 (10) | 0.0538 (12) | 0.000 | −0.0039 (9) | 0.000 |
C1 | 0.0766 (15) | 0.0732 (16) | 0.0620 (13) | −0.0116 (12) | −0.0076 (11) | −0.0068 (11) |
C2 | 0.0669 (12) | 0.0583 (12) | 0.0561 (12) | 0.0070 (10) | −0.0125 (10) | −0.0013 (10) |
C3 | 0.0539 (11) | 0.0329 (10) | 0.0541 (12) | −0.0009 (8) | −0.0034 (9) | −0.0038 (8) |
C4 | 0.0453 (9) | 0.0312 (9) | 0.0535 (10) | 0.0007 (7) | −0.0024 (8) | −0.0028 (7) |
C5 | 0.0589 (12) | 0.0308 (10) | 0.0721 (12) | −0.0013 (8) | −0.0134 (10) | −0.0072 (8) |
C6 | 0.0684 (18) | 0.0256 (12) | 0.086 (2) | 0.000 | −0.0174 (15) | 0.000 |
Geometric parameters (Å, º) top
O1—C3 | 1.319 (2) | C2—H2A | 0.9700 |
O1—C2 | 1.454 (2) | C2—H2B | 0.9700 |
O2—C3 | 1.195 (2) | C3—C4 | 1.505 (2) |
N—C4 | 1.3404 (19) | C4—C5 | 1.396 (2) |
N—C4i | 1.3404 (19) | C5—C6 | 1.378 (2) |
C1—C2 | 1.496 (3) | C5—H5A | 0.9300 |
C1—H1A | 0.9600 | C6—C5i | 1.378 (2) |
C1—H1B | 0.9600 | C6—H6A | 0.9300 |
C1—H1C | 0.9600 | | |
| | | |
C3—O1—C2 | 117.78 (15) | H2A—C2—H2B | 108.7 |
C4—N—C4i | 116.9 (2) | O2—C3—O1 | 123.63 (17) |
C2—C1—H1A | 109.5 | O2—C3—C4 | 125.02 (16) |
C2—C1—H1B | 109.5 | O1—C3—C4 | 111.28 (15) |
H1A—C1—H1B | 109.5 | N—C4—C5 | 123.38 (16) |
C2—C1—H1C | 109.5 | N—C4—C3 | 115.31 (15) |
H1A—C1—H1C | 109.5 | C5—C4—C3 | 121.30 (16) |
H1B—C1—H1C | 109.5 | C6—C5—C4 | 118.62 (17) |
O1—C2—C1 | 106.09 (17) | C6—C5—H5A | 120.7 |
O1—C2—H2A | 110.5 | C4—C5—H5A | 120.7 |
C1—C2—H2A | 110.5 | C5i—C6—C5 | 119.0 (2) |
O1—C2—H2B | 110.5 | C5i—C6—H6A | 120.5 |
C1—C2—H2B | 110.5 | C5—C6—H6A | 120.5 |
| | | |
C3—O1—C2—C1 | −177.09 (16) | O1—C3—C4—N | −176.26 (13) |
C2—O1—C3—O2 | 1.8 (3) | O2—C3—C4—C5 | −172.0 (2) |
C2—O1—C3—C4 | −175.29 (15) | O1—C3—C4—C5 | 5.0 (2) |
C4i—N—C4—C5 | 1.13 (14) | N—C4—C5—C6 | −2.2 (3) |
C4i—N—C4—C3 | −177.58 (16) | C3—C4—C5—C6 | 176.41 (13) |
O2—C3—C4—N | 6.7 (3) | C4—C5—C6—C5i | 1.03 (13) |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O2ii | 0.93 | 2.55 | 3.212 (2) | 128 |
C6—H6A···Nii | 0.93 | 2.62 | 3.552 (3) | 180 |
C6—H6A···Niii | 0.93 | 2.62 | 3.552 (3) | 180 |
Symmetry codes: (ii) x, y+1, z; (iii) −x, y+1, −z+1/2. |
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