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The spectroscopically uncharacterized title compound, C15H15NO5, has been identified crystallographically. The assignment of a cyano substituent in preference to the isocyano (isonitrile) alternative can be made on the basis of the refinement and the observed geometry. The pyran ring has a half-chair conformation. The methoxy and acetate ester substituents lie, respectively, approximately in and perpendicular to the aromatic ring.
Supporting information
CCDC reference: 203006
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.093
- wR factor = 0.306
- Data-to-parameter ratio = 13.2
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25
Weighted R factor given 0.306
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(5) - C(12) = 1.44 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: DIF4 (Stoe & Cie, 1988); cell refinement: DIF4; data reduction: local programs; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
5-Cyano-7-methoxy-2,2-dimethyl-4-oxochroman-6-yl acetate
top
Crystal data top
C15H15NO5 | F(000) = 608 |
Mr = 289.28 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3563 (6) Å | Cell parameters from 32 reflections |
b = 15.0152 (11) Å | θ = 10.0–12.5° |
c = 11.7498 (8) Å | µ = 0.10 mm−1 |
β = 98.089 (8)° | T = 295 K |
V = 1459.60 (18) Å3 | Block, colourless |
Z = 4 | 0.65 × 0.30 × 0.25 mm |
Data collection top
Stoe-Siemens four-circle diffractometer | Rint = 0.019 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.2° |
Graphite monochromator | h = −9→1 |
ω/θ scans | k = 0→17 |
2981 measured reflections | l = −13→13 |
2558 independent reflections | 3 standard reflections every 60 min |
1790 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.093 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.306 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.1867P)2 + 0.5937P] where P = (Fo2 + 2Fc2)/3 |
2558 reflections | (Δ/σ)max < 0.001 |
194 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.5946 (3) | 0.71584 (17) | 0.0910 (3) | 0.0647 (9) | |
C2 | 0.6495 (5) | 0.8089 (3) | 0.0950 (3) | 0.0581 (10) | |
C3 | 0.6412 (5) | 0.8448 (3) | 0.2146 (4) | 0.0638 (11) | |
H3A | 0.7198 | 0.8137 | 0.2690 | 0.077* | |
H3B | 0.6703 | 0.9074 | 0.2167 | 0.077* | |
C4 | 0.4775 (5) | 0.8349 (3) | 0.2510 (3) | 0.0581 (10) | |
C4A | 0.3906 (4) | 0.7537 (2) | 0.2095 (3) | 0.0507 (9) | |
C5 | 0.2441 (4) | 0.7269 (2) | 0.2476 (3) | 0.0502 (9) | |
C6 | 0.1737 (4) | 0.6473 (2) | 0.2118 (3) | 0.0510 (9) | |
C7 | 0.2423 (4) | 0.5912 (2) | 0.1371 (3) | 0.0515 (9) | |
C8 | 0.3837 (4) | 0.6168 (2) | 0.0990 (3) | 0.0544 (9) | |
H8 | 0.4309 | 0.5799 | 0.0495 | 0.065* | |
C8A | 0.4567 (4) | 0.6974 (2) | 0.1340 (3) | 0.0523 (9) | |
C9 | 0.8216 (5) | 0.8030 (3) | 0.0674 (4) | 0.0710 (12) | |
H9A | 0.8682 | 0.8615 | 0.0694 | 0.107* | |
H9B | 0.8206 | 0.7779 | −0.0078 | 0.107* | |
H9C | 0.8847 | 0.7658 | 0.1232 | 0.107* | |
C10 | 0.5421 (5) | 0.8617 (3) | 0.0045 (4) | 0.0743 (12) | |
H10A | 0.5776 | 0.9225 | 0.0060 | 0.112* | |
H10B | 0.4324 | 0.8593 | 0.0202 | 0.112* | |
H10C | 0.5480 | 0.8367 | −0.0699 | 0.112* | |
O11 | 0.4235 (4) | 0.88986 (19) | 0.3124 (3) | 0.0734 (9) | |
C12 | 0.1623 (5) | 0.7799 (3) | 0.3243 (4) | 0.0613 (10) | |
N13 | 0.0881 (5) | 0.8166 (3) | 0.3831 (4) | 0.0898 (14) | |
O14 | 0.0230 (3) | 0.62416 (17) | 0.2420 (2) | 0.0560 (8) | |
C15 | 0.0241 (5) | 0.5594 (3) | 0.3234 (3) | 0.0628 (11) | |
O16 | 0.1465 (4) | 0.5340 (2) | 0.3798 (3) | 0.0857 (11) | |
C17 | −0.1431 (6) | 0.5264 (4) | 0.3277 (4) | 0.0838 (14) | |
H17A | −0.1692 | 0.4811 | 0.2704 | 0.126* | |
H17B | −0.2181 | 0.5748 | 0.3131 | 0.126* | |
H17C | −0.1497 | 0.5019 | 0.4023 | 0.126* | |
O18 | 0.1596 (3) | 0.51628 (17) | 0.1072 (2) | 0.0594 (8) | |
C19 | 0.2147 (5) | 0.4604 (3) | 0.0201 (3) | 0.0616 (10) | |
H19A | 0.1450 | 0.4095 | 0.0066 | 0.092* | |
H19B | 0.3231 | 0.4409 | 0.0459 | 0.092* | |
H19C | 0.2123 | 0.4936 | −0.0499 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0579 (16) | 0.0536 (16) | 0.088 (2) | −0.0078 (12) | 0.0311 (14) | −0.0100 (14) |
C2 | 0.055 (2) | 0.054 (2) | 0.068 (2) | −0.0079 (17) | 0.0190 (18) | −0.0082 (17) |
C3 | 0.058 (2) | 0.063 (2) | 0.071 (2) | −0.0095 (18) | 0.0104 (18) | −0.0112 (19) |
C4 | 0.062 (2) | 0.057 (2) | 0.055 (2) | −0.0005 (18) | 0.0073 (17) | −0.0062 (17) |
C4A | 0.0506 (19) | 0.0484 (19) | 0.054 (2) | 0.0023 (15) | 0.0090 (16) | −0.0012 (15) |
C5 | 0.052 (2) | 0.0505 (19) | 0.0493 (19) | 0.0048 (16) | 0.0098 (16) | −0.0030 (15) |
C6 | 0.0485 (19) | 0.0507 (19) | 0.0549 (19) | 0.0042 (16) | 0.0115 (16) | 0.0018 (16) |
C7 | 0.051 (2) | 0.0474 (19) | 0.058 (2) | 0.0007 (15) | 0.0118 (15) | −0.0003 (15) |
C8 | 0.057 (2) | 0.048 (2) | 0.061 (2) | −0.0013 (16) | 0.0183 (17) | −0.0090 (16) |
C8A | 0.0462 (19) | 0.052 (2) | 0.061 (2) | 0.0007 (16) | 0.0133 (16) | −0.0015 (16) |
C9 | 0.058 (2) | 0.068 (3) | 0.092 (3) | −0.007 (2) | 0.027 (2) | 0.000 (2) |
C10 | 0.069 (3) | 0.078 (3) | 0.075 (3) | −0.003 (2) | 0.008 (2) | 0.006 (2) |
O11 | 0.0738 (19) | 0.0669 (18) | 0.083 (2) | −0.0050 (15) | 0.0220 (16) | −0.0218 (15) |
C12 | 0.059 (2) | 0.064 (2) | 0.063 (2) | 0.0006 (19) | 0.0162 (19) | −0.0080 (19) |
N13 | 0.082 (3) | 0.093 (3) | 0.102 (3) | −0.006 (2) | 0.040 (2) | −0.029 (2) |
O14 | 0.0498 (14) | 0.0576 (16) | 0.0628 (15) | 0.0017 (11) | 0.0155 (12) | 0.0025 (12) |
C15 | 0.073 (3) | 0.063 (2) | 0.056 (2) | −0.005 (2) | 0.023 (2) | −0.0026 (18) |
O16 | 0.078 (2) | 0.100 (3) | 0.080 (2) | 0.0012 (19) | 0.0121 (17) | 0.0300 (19) |
C17 | 0.077 (3) | 0.094 (3) | 0.087 (3) | −0.021 (3) | 0.034 (3) | −0.002 (3) |
O18 | 0.0552 (15) | 0.0541 (15) | 0.0717 (17) | −0.0059 (12) | 0.0189 (12) | −0.0090 (12) |
C19 | 0.067 (2) | 0.054 (2) | 0.065 (2) | −0.0035 (18) | 0.0129 (19) | −0.0109 (18) |
Geometric parameters (Å, º) top
O1—C2 | 1.470 (4) | C8—C8A | 1.391 (5) |
O1—C8A | 1.350 (4) | C9—H9A | 0.960 |
C2—C3 | 1.515 (5) | C9—H9B | 0.960 |
C2—C9 | 1.521 (5) | C9—H9C | 0.960 |
C2—C10 | 1.515 (6) | C10—H10A | 0.960 |
C3—H3A | 0.970 | C10—H10B | 0.960 |
C3—H3B | 0.970 | C10—H10C | 0.960 |
C3—C4 | 1.497 (6) | C12—N13 | 1.134 (5) |
C4—C4A | 1.467 (5) | O14—C15 | 1.363 (5) |
C4—O11 | 1.223 (5) | C15—O16 | 1.200 (5) |
C4A—C5 | 1.419 (5) | C15—C17 | 1.490 (6) |
C4A—C8A | 1.395 (5) | C17—H17A | 0.960 |
C5—C6 | 1.371 (5) | C17—H17B | 0.960 |
C5—C12 | 1.444 (5) | C17—H17C | 0.960 |
C6—C7 | 1.396 (5) | O18—C19 | 1.448 (4) |
C6—O14 | 1.400 (4) | C19—H19A | 0.960 |
C7—C8 | 1.376 (5) | C19—H19B | 0.960 |
C7—O18 | 1.341 (4) | C19—H19C | 0.960 |
C8—H8 | 0.930 | | |
| | | |
C2—O1—C8A | 117.5 (3) | O1—C8A—C8 | 115.4 (3) |
O1—C2—C3 | 108.2 (3) | C4A—C8A—C8 | 121.3 (3) |
O1—C2—C9 | 103.7 (3) | C2—C9—H9A | 109.5 |
O1—C2—C10 | 108.9 (3) | C2—C9—H9B | 109.5 |
C3—C2—C9 | 112.8 (3) | C2—C9—H9C | 109.5 |
C3—C2—C10 | 111.4 (3) | H9A—C9—H9B | 109.5 |
C9—C2—C10 | 111.5 (4) | H9A—C9—H9C | 109.5 |
C2—C3—H3A | 108.9 | H9B—C9—H9C | 109.5 |
C2—C3—H3B | 108.9 | C2—C10—H10A | 109.5 |
C2—C3—C4 | 113.2 (3) | C2—C10—H10B | 109.5 |
H3A—C3—H3B | 107.8 | C2—C10—H10C | 109.5 |
H3A—C3—C4 | 108.9 | H10A—C10—H10B | 109.5 |
H3B—C3—C4 | 108.9 | H10A—C10—H10C | 109.5 |
C3—C4—C4A | 114.7 (3) | H10B—C10—H10C | 109.5 |
C3—C4—O11 | 121.9 (4) | C5—C12—N13 | 174.4 (5) |
C4A—C4—O11 | 123.4 (4) | C6—O14—C15 | 116.0 (3) |
C4—C4A—C5 | 122.7 (3) | O14—C15—O16 | 122.4 (4) |
C4—C4A—C8A | 119.6 (3) | O14—C15—C17 | 110.3 (4) |
C5—C4A—C8A | 117.7 (3) | O16—C15—C17 | 127.3 (4) |
C4A—C5—C6 | 120.1 (3) | C15—C17—H17A | 109.5 |
C4A—C5—C12 | 123.0 (3) | C15—C17—H17B | 109.5 |
C6—C5—C12 | 116.9 (3) | C15—C17—H17C | 109.5 |
C5—C6—C7 | 121.5 (3) | H17A—C17—H17B | 109.5 |
C5—C6—O14 | 120.1 (3) | H17A—C17—H17C | 109.5 |
C7—C6—O14 | 118.2 (3) | H17B—C17—H17C | 109.5 |
C6—C7—C8 | 118.9 (3) | C7—O18—C19 | 118.0 (3) |
C6—C7—O18 | 115.4 (3) | O18—C19—H19A | 109.5 |
C8—C7—O18 | 125.7 (3) | O18—C19—H19B | 109.5 |
C7—C8—H8 | 119.7 | O18—C19—H19C | 109.5 |
C7—C8—C8A | 120.5 (3) | H19A—C19—H19B | 109.5 |
H8—C8—C8A | 119.7 | H19A—C19—H19C | 109.5 |
O1—C8A—C4A | 123.3 (3) | H19B—C19—H19C | 109.5 |
| | | |
C8A—O1—C2—C3 | 47.3 (4) | C5—C6—C7—C8 | 0.0 (5) |
C8A—O1—C2—C9 | 167.3 (3) | C5—C6—C7—O18 | −178.8 (3) |
C8A—O1—C2—C10 | −73.9 (4) | O14—C6—C7—C8 | 174.6 (3) |
O1—C2—C3—C4 | −54.9 (4) | O14—C6—C7—O18 | −4.1 (5) |
C9—C2—C3—C4 | −169.1 (4) | C6—C7—C8—C8A | −0.2 (6) |
C10—C2—C3—C4 | 64.7 (5) | O18—C7—C8—C8A | 178.4 (3) |
C2—C3—C4—C4A | 35.2 (5) | C2—O1—C8A—C4A | −19.1 (5) |
C2—C3—C4—O11 | −146.1 (4) | C2—O1—C8A—C8 | 161.7 (3) |
C3—C4—C4A—C5 | 171.3 (3) | C7—C8—C8A—O1 | −179.8 (3) |
C3—C4—C4A—C8A | −5.3 (5) | C7—C8—C8A—C4A | 0.9 (6) |
O11—C4—C4A—C5 | −7.4 (6) | C4—C4A—C8A—O1 | −3.8 (6) |
O11—C4—C4A—C8A | 176.0 (4) | C4—C4A—C8A—C8 | 175.5 (3) |
C4—C4A—C5—C6 | −175.6 (3) | C5—C4A—C8A—O1 | 179.5 (3) |
C4—C4A—C5—C12 | 4.3 (6) | C5—C4A—C8A—C8 | −1.3 (5) |
C8A—C4A—C5—C6 | 1.1 (5) | C5—C6—O14—C15 | −106.9 (4) |
C8A—C4A—C5—C12 | −179.0 (3) | C7—C6—O14—C15 | 78.4 (4) |
C4A—C5—C6—C7 | −0.4 (5) | C6—O14—C15—O16 | 12.0 (6) |
C4A—C5—C6—O14 | −174.9 (3) | C6—O14—C15—C17 | −166.7 (3) |
C12—C5—C6—C7 | 179.7 (3) | C6—C7—O18—C19 | 173.1 (3) |
C12—C5—C6—O14 | 5.1 (5) | C8—C7—O18—C19 | −5.5 (5) |
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