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The title compound, C
16H
16N
2O
5, is a β-ketoether derivative closely related to natural 8,4′-oxyneolignans, which are of interest because of their moderate antifungal activity against systemic mycosis. The nitro group is not coplanar with the aromatic ring, as shown by a torsion angle of 47.2 (4)°. The molecules are linked by two non-classical intermolecular C—H
O hydrogen bonds with distances between donors and acceptors of 3.441 (5) and 3.539 (5) Å, leading to the formation of molecular stacking perpendicular to the
bc plane.
Supporting information
CCDC reference: 263668
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.052
- wR factor = 0.162
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-(4-Methoxyphenyl)-2-(6-methyl-2-nitro-3-pyridyloxy)propan-1-one
top
Crystal data top
C16H16N2O5 | F(000) = 664 |
Mr = 316.31 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Melting point = 403–405 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.185 (2) Å | Cell parameters from 25 reflections |
b = 14.756 (3) Å | θ = 10.0–13.6° |
c = 15.092 (5) Å | µ = 0.10 mm−1 |
β = 121.73 (2)° | T = 298 K |
V = 1550.3 (8) Å3 | Block, light brown |
Z = 4 | 0.35 × 0.25 × 0.25 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.1° |
Graphite monochromator | h = −10→10 |
Non–profiled ω/2θ scans | k = −19→0 |
3883 measured reflections | l = −10→19 |
3727 independent reflections | 2 standard reflections every 120 min |
1857 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0812P)2 + 0.4785P] where P = (Fo2 + 2Fc2)/3 |
2729 reflections | (Δ/σ)max = 0.006 |
226 parameters | Δρmax = 0.38 e Å−3 |
13 restraints | Δρmin = −0.30 e Å−3 |
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 | −0.4986 (4) | 0.8451 (2) | 0.4040 (2) | 0.1123 (11) | |
O2 | −0.3632 (4) | 0.8142 (2) | 0.32131 (19) | 0.0994 (9) | |
O3 | 1.1032 (3) | 0.89478 (18) | 0.91383 (16) | 0.0739 (7) | |
O4 | 0.2032 (3) | 0.93396 (15) | 0.66460 (16) | 0.0645 (6) | |
O5 | 0.0173 (2) | 0.84786 (13) | 0.47999 (15) | 0.0561 (5) | |
N1 | −0.3689 (3) | 0.81293 (17) | 0.39900 (19) | 0.0562 (6) | |
N2 | −0.2807 (3) | 0.70685 (16) | 0.53122 (18) | 0.0517 (6) | |
C1 | −0.1541 (4) | 0.6568 (2) | 0.6123 (2) | 0.0562 (7) | |
C2 | 0.0405 (5) | 0.6650 (2) | 0.6503 (2) | 0.0604 (8) | |
H2 | 0.1276 | 0.6281 | 0.7049 | 0.073* | |
C3 | 0.1062 (4) | 0.7269 (2) | 0.6084 (2) | 0.0558 (7) | |
H3 | 0.2371 | 0.7326 | 0.6348 | 0.067* | |
C4 | −0.0243 (3) | 0.78097 (18) | 0.5265 (2) | 0.0472 (6) | |
C5 | −0.2159 (3) | 0.76473 (18) | 0.4908 (2) | 0.0458 (6) | |
C6 | 0.2158 (3) | 0.8725 (2) | 0.5234 (2) | 0.0496 (7) | |
H6 | 0.2882 | 0.8203 | 0.5218 | 0.060* | |
C7 | 0.3056 (4) | 0.90696 (18) | 0.6345 (2) | 0.0477 (6) | |
C8 | 0.5170 (3) | 0.90653 (18) | 0.7025 (2) | 0.0436 (6) | |
C9 | 0.6366 (4) | 0.8701 (2) | 0.6729 (2) | 0.0535 (7) | |
H9 | 0.5836 | 0.8475 | 0.6057 | 0.064* | |
C10 | 0.8329 (4) | 0.8664 (2) | 0.7406 (2) | 0.0584 (8) | |
H10 | 0.9107 | 0.8423 | 0.7187 | 0.070* | |
C11 | 0.9128 (4) | 0.8982 (2) | 0.8398 (2) | 0.0526 (7) | |
C12 | 0.7957 (4) | 0.9377 (2) | 0.8702 (2) | 0.0615 (8) | |
H12 | 0.8499 | 0.9616 | 0.9368 | 0.074* | |
C13 | 0.6019 (4) | 0.9415 (2) | 0.8028 (2) | 0.0555 (7) | |
H13 | 0.5251 | 0.9680 | 0.8242 | 0.067* | |
C14 | −0.2326 (6) | 0.5935 (3) | 0.6580 (3) | 0.0829 (11) | |
H14A | −0.143 (5) | 0.548 (2) | 0.705 (3) | 0.124* | |
H14B | −0.343 (5) | 0.565 (3) | 0.604 (3) | 0.124* | |
H14C | −0.262 (6) | 0.629 (2) | 0.700 (3) | 0.124* | |
C15 | 0.2127 (4) | 0.9465 (2) | 0.4540 (2) | 0.0645 (8) | |
H15A | 0.1554 | 0.9240 | 0.3841 | 0.097* | |
H15B | 0.3417 | 0.9659 | 0.4787 | 0.097* | |
H15C | 0.1391 | 0.9968 | 0.4547 | 0.097* | |
C16 | 1.2239 (5) | 0.8459 (3) | 0.8884 (3) | 0.0810 (11) | |
H16A | 1.235 (6) | 0.875 (3) | 0.833 (3) | 0.122* | |
H16B | 1.346 (4) | 0.847 (2) | 0.953 (2) | 0.122* | |
H16C | 1.187 (6) | 0.784 (2) | 0.873 (3) | 0.122* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0757 (18) | 0.170 (3) | 0.094 (2) | 0.0599 (18) | 0.0471 (16) | 0.0295 (19) |
O2 | 0.0716 (17) | 0.159 (3) | 0.0642 (15) | 0.0218 (16) | 0.0336 (13) | 0.0264 (16) |
O3 | 0.0349 (11) | 0.1200 (19) | 0.0562 (13) | −0.0068 (11) | 0.0166 (10) | 0.0024 (12) |
O4 | 0.0401 (11) | 0.0878 (15) | 0.0714 (13) | 0.0067 (10) | 0.0333 (10) | −0.0097 (12) |
O5 | 0.0303 (9) | 0.0705 (13) | 0.0600 (12) | −0.0031 (9) | 0.0186 (9) | 0.0085 (10) |
N1 | 0.0364 (12) | 0.0773 (17) | 0.0518 (14) | −0.0011 (12) | 0.0209 (11) | 0.0007 (12) |
N2 | 0.0471 (13) | 0.0560 (14) | 0.0555 (14) | −0.0085 (11) | 0.0294 (12) | −0.0079 (12) |
C1 | 0.0574 (18) | 0.0580 (18) | 0.0563 (17) | −0.0048 (14) | 0.0320 (15) | −0.0031 (14) |
C2 | 0.0586 (18) | 0.0569 (17) | 0.0592 (17) | 0.0050 (14) | 0.0265 (15) | 0.0037 (15) |
C3 | 0.0377 (14) | 0.0636 (18) | 0.0576 (17) | 0.0027 (13) | 0.0192 (14) | 0.0007 (14) |
C4 | 0.0348 (14) | 0.0533 (16) | 0.0507 (15) | −0.0048 (12) | 0.0207 (13) | −0.0039 (13) |
C5 | 0.0352 (13) | 0.0523 (15) | 0.0453 (14) | 0.0000 (12) | 0.0181 (12) | −0.0051 (12) |
C6 | 0.0260 (12) | 0.0651 (17) | 0.0521 (15) | −0.0007 (12) | 0.0166 (12) | −0.0021 (14) |
C7 | 0.0369 (14) | 0.0529 (16) | 0.0569 (16) | 0.0035 (12) | 0.0271 (13) | 0.0036 (13) |
C8 | 0.0331 (13) | 0.0524 (15) | 0.0465 (14) | −0.0017 (11) | 0.0217 (12) | −0.0030 (12) |
C9 | 0.0355 (14) | 0.0767 (19) | 0.0454 (15) | 0.0029 (13) | 0.0193 (12) | −0.0075 (14) |
C10 | 0.0374 (15) | 0.082 (2) | 0.0578 (18) | 0.0062 (14) | 0.0265 (14) | −0.0011 (15) |
C11 | 0.0352 (14) | 0.0682 (18) | 0.0479 (16) | −0.0056 (13) | 0.0173 (13) | 0.0041 (14) |
C12 | 0.0465 (17) | 0.088 (2) | 0.0472 (16) | −0.0152 (15) | 0.0227 (14) | −0.0137 (15) |
C13 | 0.0454 (16) | 0.0674 (19) | 0.0606 (17) | −0.0053 (14) | 0.0326 (15) | −0.0126 (15) |
C14 | 0.088 (3) | 0.079 (3) | 0.089 (3) | −0.007 (2) | 0.052 (2) | 0.016 (2) |
C15 | 0.0372 (15) | 0.094 (2) | 0.0611 (18) | −0.0034 (15) | 0.0249 (14) | 0.0117 (17) |
C16 | 0.0371 (17) | 0.110 (3) | 0.083 (2) | 0.0148 (18) | 0.0221 (17) | 0.021 (2) |
Geometric parameters (Å, º) top
O1—N1 | 1.202 (3) | C7—C8 | 1.476 (4) |
O2—N1 | 1.198 (3) | C8—C9 | 1.381 (4) |
O3—C11 | 1.359 (3) | C8—C13 | 1.390 (4) |
O3—C16 | 1.429 (4) | C9—C10 | 1.379 (4) |
O4—C7 | 1.211 (3) | C9—H9 | 0.9300 |
O5—C4 | 1.354 (3) | C10—C11 | 1.363 (4) |
O5—C6 | 1.442 (3) | C10—H10 | 0.9300 |
N1—C5 | 1.472 (3) | C11—C12 | 1.389 (4) |
N2—C5 | 1.313 (3) | C12—C13 | 1.363 (4) |
N2—C1 | 1.335 (4) | C12—H12 | 0.9300 |
C1—C2 | 1.386 (4) | C13—H13 | 0.9300 |
C1—C14 | 1.493 (5) | C14—H14A | 0.97 (3) |
C2—C3 | 1.372 (4) | C14—H14B | 0.94 (3) |
C2—H2 | 0.9300 | C14—H14C | 0.94 (3) |
C3—C4 | 1.384 (4) | C15—H15A | 0.9600 |
C3—H3 | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.385 (3) | C15—H15C | 0.9600 |
C6—C15 | 1.505 (4) | C16—H16A | 0.98 (3) |
C6—C7 | 1.521 (4) | C16—H16B | 0.96 (3) |
C6—H6 | 0.9800 | C16—H16C | 0.96 (3) |
| | | |
C11—O3—C16 | 117.0 (2) | C10—C9—C8 | 121.5 (3) |
C4—O5—C6 | 118.6 (2) | C10—C9—H9 | 119.2 |
O2—N1—O1 | 123.1 (3) | C8—C9—H9 | 119.2 |
O2—N1—C5 | 118.5 (2) | C11—C10—C9 | 120.0 (3) |
O1—N1—C5 | 118.3 (3) | C11—C10—H10 | 120.0 |
C5—N2—C1 | 118.5 (2) | C9—C10—H10 | 120.0 |
N2—C1—C2 | 120.1 (3) | O3—C11—C10 | 124.8 (3) |
N2—C1—C14 | 117.0 (3) | O3—C11—C12 | 115.8 (3) |
C2—C1—C14 | 122.9 (3) | C10—C11—C12 | 119.4 (2) |
C3—C2—C1 | 120.7 (3) | C13—C12—C11 | 120.4 (3) |
C3—C2—H2 | 119.7 | C13—C12—H12 | 119.8 |
C1—C2—H2 | 119.7 | C11—C12—H12 | 119.8 |
C2—C3—C4 | 119.4 (3) | C12—C13—C8 | 121.0 (3) |
C2—C3—H3 | 120.3 | C12—C13—H13 | 119.5 |
C4—C3—H3 | 120.3 | C8—C13—H13 | 119.5 |
O5—C4—C3 | 126.6 (2) | C1—C14—H14A | 115 (3) |
O5—C4—C5 | 117.8 (2) | C1—C14—H14B | 109 (3) |
C3—C4—C5 | 115.6 (3) | H14A—C14—H14B | 109 (3) |
N2—C5—C4 | 125.7 (2) | C1—C14—H14C | 107 (3) |
N2—C5—N1 | 113.6 (2) | H14A—C14—H14C | 105 (3) |
C4—C5—N1 | 120.7 (2) | H14B—C14—H14C | 111 (3) |
O5—C6—C15 | 105.3 (2) | C6—C15—H15A | 109.5 |
O5—C6—C7 | 111.2 (2) | C6—C15—H15B | 109.5 |
C15—C6—C7 | 110.3 (2) | H15A—C15—H15B | 109.5 |
O5—C6—H6 | 110.0 | C6—C15—H15C | 109.5 |
C15—C6—H6 | 110.0 | H15A—C15—H15C | 109.5 |
C7—C6—H6 | 110.0 | H15B—C15—H15C | 109.5 |
O4—C7—C8 | 122.0 (3) | O3—C16—H16A | 113 (3) |
O4—C7—C6 | 119.6 (2) | O3—C16—H16B | 103 (2) |
C8—C7—C6 | 118.3 (2) | H16A—C16—H16B | 110 (3) |
C9—C8—C13 | 117.6 (2) | O3—C16—H16C | 112 (3) |
C9—C8—C7 | 123.2 (2) | H16A—C16—H16C | 112 (3) |
C13—C8—C7 | 119.1 (2) | H16B—C16—H16C | 107 (3) |
| | | |
C5—N2—C1—C2 | −1.5 (4) | O5—C6—C7—O4 | −20.1 (4) |
C5—N2—C1—C14 | 178.4 (3) | C15—C6—C7—O4 | 96.3 (3) |
N2—C1—C2—C3 | 2.7 (4) | O5—C6—C7—C8 | 160.1 (2) |
C14—C1—C2—C3 | −177.2 (3) | C15—C6—C7—C8 | −83.5 (3) |
C1—C2—C3—C4 | −0.7 (4) | O4—C7—C8—C9 | 175.1 (3) |
C6—O5—C4—C3 | −5.7 (4) | C6—C7—C8—C9 | −5.1 (4) |
C6—O5—C4—C5 | 173.2 (2) | O4—C7—C8—C13 | −2.6 (4) |
C2—C3—C4—O5 | 176.6 (3) | C6—C7—C8—C13 | 177.2 (2) |
C2—C3—C4—C5 | −2.3 (4) | C13—C8—C9—C10 | 1.5 (4) |
C1—N2—C5—C4 | −1.8 (4) | C7—C8—C9—C10 | −176.3 (3) |
C1—N2—C5—N1 | 177.3 (2) | C8—C9—C10—C11 | 0.8 (5) |
O5—C4—C5—N2 | −175.3 (2) | C16—O3—C11—C10 | −6.8 (5) |
C3—C4—C5—N2 | 3.7 (4) | C16—O3—C11—C12 | 173.4 (3) |
O5—C4—C5—N1 | 5.6 (4) | C9—C10—C11—O3 | 177.4 (3) |
C3—C4—C5—N1 | −175.4 (2) | C9—C10—C11—C12 | −2.8 (5) |
O2—N1—C5—N2 | −129.0 (3) | O3—C11—C12—C13 | −177.7 (3) |
O1—N1—C5—N2 | 47.2 (4) | C10—C11—C12—C13 | 2.5 (5) |
O2—N1—C5—C4 | 50.1 (4) | C11—C12—C13—C8 | −0.2 (5) |
O1—N1—C5—C4 | −133.7 (3) | C9—C8—C13—C12 | −1.7 (4) |
C4—O5—C6—C15 | 179.2 (2) | C7—C8—C13—C12 | 176.1 (3) |
C4—O5—C6—C7 | −61.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14C···O2i | 0.94 (3) | 2.52 (3) | 3.441 (5) | 166 (4) |
C16—H16A···O4ii | 0.98 (3) | 2.57 (3) | 3.539 (5) | 169 (3) |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x+1, y, z. |
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