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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023000/bt6217sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023000/bt6217Isup2.hkl
Contains datablock I

CCDC reference: 203006

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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
C15H15NO5F(000) = 608
Mr = 289.28Dx = 1.316 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.3563 (6) ÅCell parameters from 32 reflections
b = 15.0152 (11) Åθ = 10.0–12.5°
c = 11.7498 (8) ŵ = 0.10 mm1
β = 98.089 (8)°T = 295 K
V = 1459.60 (18) Å3Block, colourless
Z = 40.65 × 0.30 × 0.25 mm
Data collection top
Stoe-Siemens four-circle
diffractometer
Rint = 0.019
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 91
ω/θ scansk = 017
2981 measured reflectionsl = 1313
2558 independent reflections3 standard reflections every 60 min
1790 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.093Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.306H-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 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = 0.32 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5946 (3)0.71584 (17)0.0910 (3)0.0647 (9)
C20.6495 (5)0.8089 (3)0.0950 (3)0.0581 (10)
C30.6412 (5)0.8448 (3)0.2146 (4)0.0638 (11)
H3A0.71980.81370.26900.077*
H3B0.67030.90740.21670.077*
C40.4775 (5)0.8349 (3)0.2510 (3)0.0581 (10)
C4A0.3906 (4)0.7537 (2)0.2095 (3)0.0507 (9)
C50.2441 (4)0.7269 (2)0.2476 (3)0.0502 (9)
C60.1737 (4)0.6473 (2)0.2118 (3)0.0510 (9)
C70.2423 (4)0.5912 (2)0.1371 (3)0.0515 (9)
C80.3837 (4)0.6168 (2)0.0990 (3)0.0544 (9)
H80.43090.57990.04950.065*
C8A0.4567 (4)0.6974 (2)0.1340 (3)0.0523 (9)
C90.8216 (5)0.8030 (3)0.0674 (4)0.0710 (12)
H9A0.86820.86150.06940.107*
H9B0.82060.77790.00780.107*
H9C0.88470.76580.12320.107*
C100.5421 (5)0.8617 (3)0.0045 (4)0.0743 (12)
H10A0.57760.92250.00600.112*
H10B0.43240.85930.02020.112*
H10C0.54800.83670.06990.112*
O110.4235 (4)0.88986 (19)0.3124 (3)0.0734 (9)
C120.1623 (5)0.7799 (3)0.3243 (4)0.0613 (10)
N130.0881 (5)0.8166 (3)0.3831 (4)0.0898 (14)
O140.0230 (3)0.62416 (17)0.2420 (2)0.0560 (8)
C150.0241 (5)0.5594 (3)0.3234 (3)0.0628 (11)
O160.1465 (4)0.5340 (2)0.3798 (3)0.0857 (11)
C170.1431 (6)0.5264 (4)0.3277 (4)0.0838 (14)
H17A0.16920.48110.27040.126*
H17B0.21810.57480.31310.126*
H17C0.14970.50190.40230.126*
O180.1596 (3)0.51628 (17)0.1072 (2)0.0594 (8)
C190.2147 (5)0.4604 (3)0.0201 (3)0.0616 (10)
H19A0.14500.40950.00660.092*
H19B0.32310.44090.04590.092*
H19C0.21230.49360.04990.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0579 (16)0.0536 (16)0.088 (2)0.0078 (12)0.0311 (14)0.0100 (14)
C20.055 (2)0.054 (2)0.068 (2)0.0079 (17)0.0190 (18)0.0082 (17)
C30.058 (2)0.063 (2)0.071 (2)0.0095 (18)0.0104 (18)0.0112 (19)
C40.062 (2)0.057 (2)0.055 (2)0.0005 (18)0.0073 (17)0.0062 (17)
C4A0.0506 (19)0.0484 (19)0.054 (2)0.0023 (15)0.0090 (16)0.0012 (15)
C50.052 (2)0.0505 (19)0.0493 (19)0.0048 (16)0.0098 (16)0.0030 (15)
C60.0485 (19)0.0507 (19)0.0549 (19)0.0042 (16)0.0115 (16)0.0018 (16)
C70.051 (2)0.0474 (19)0.058 (2)0.0007 (15)0.0118 (15)0.0003 (15)
C80.057 (2)0.048 (2)0.061 (2)0.0013 (16)0.0183 (17)0.0090 (16)
C8A0.0462 (19)0.052 (2)0.061 (2)0.0007 (16)0.0133 (16)0.0015 (16)
C90.058 (2)0.068 (3)0.092 (3)0.007 (2)0.027 (2)0.000 (2)
C100.069 (3)0.078 (3)0.075 (3)0.003 (2)0.008 (2)0.006 (2)
O110.0738 (19)0.0669 (18)0.083 (2)0.0050 (15)0.0220 (16)0.0218 (15)
C120.059 (2)0.064 (2)0.063 (2)0.0006 (19)0.0162 (19)0.0080 (19)
N130.082 (3)0.093 (3)0.102 (3)0.006 (2)0.040 (2)0.029 (2)
O140.0498 (14)0.0576 (16)0.0628 (15)0.0017 (11)0.0155 (12)0.0025 (12)
C150.073 (3)0.063 (2)0.056 (2)0.005 (2)0.023 (2)0.0026 (18)
O160.078 (2)0.100 (3)0.080 (2)0.0012 (19)0.0121 (17)0.0300 (19)
C170.077 (3)0.094 (3)0.087 (3)0.021 (3)0.034 (3)0.002 (3)
O180.0552 (15)0.0541 (15)0.0717 (17)0.0059 (12)0.0189 (12)0.0090 (12)
C190.067 (2)0.054 (2)0.065 (2)0.0035 (18)0.0129 (19)0.0109 (18)
Geometric parameters (Å, º) top
O1—C21.470 (4)C8—C8A1.391 (5)
O1—C8A1.350 (4)C9—H9A0.960
C2—C31.515 (5)C9—H9B0.960
C2—C91.521 (5)C9—H9C0.960
C2—C101.515 (6)C10—H10A0.960
C3—H3A0.970C10—H10B0.960
C3—H3B0.970C10—H10C0.960
C3—C41.497 (6)C12—N131.134 (5)
C4—C4A1.467 (5)O14—C151.363 (5)
C4—O111.223 (5)C15—O161.200 (5)
C4A—C51.419 (5)C15—C171.490 (6)
C4A—C8A1.395 (5)C17—H17A0.960
C5—C61.371 (5)C17—H17B0.960
C5—C121.444 (5)C17—H17C0.960
C6—C71.396 (5)O18—C191.448 (4)
C6—O141.400 (4)C19—H19A0.960
C7—C81.376 (5)C19—H19B0.960
C7—O181.341 (4)C19—H19C0.960
C8—H80.930
C2—O1—C8A117.5 (3)O1—C8A—C8115.4 (3)
O1—C2—C3108.2 (3)C4A—C8A—C8121.3 (3)
O1—C2—C9103.7 (3)C2—C9—H9A109.5
O1—C2—C10108.9 (3)C2—C9—H9B109.5
C3—C2—C9112.8 (3)C2—C9—H9C109.5
C3—C2—C10111.4 (3)H9A—C9—H9B109.5
C9—C2—C10111.5 (4)H9A—C9—H9C109.5
C2—C3—H3A108.9H9B—C9—H9C109.5
C2—C3—H3B108.9C2—C10—H10A109.5
C2—C3—C4113.2 (3)C2—C10—H10B109.5
H3A—C3—H3B107.8C2—C10—H10C109.5
H3A—C3—C4108.9H10A—C10—H10B109.5
H3B—C3—C4108.9H10A—C10—H10C109.5
C3—C4—C4A114.7 (3)H10B—C10—H10C109.5
C3—C4—O11121.9 (4)C5—C12—N13174.4 (5)
C4A—C4—O11123.4 (4)C6—O14—C15116.0 (3)
C4—C4A—C5122.7 (3)O14—C15—O16122.4 (4)
C4—C4A—C8A119.6 (3)O14—C15—C17110.3 (4)
C5—C4A—C8A117.7 (3)O16—C15—C17127.3 (4)
C4A—C5—C6120.1 (3)C15—C17—H17A109.5
C4A—C5—C12123.0 (3)C15—C17—H17B109.5
C6—C5—C12116.9 (3)C15—C17—H17C109.5
C5—C6—C7121.5 (3)H17A—C17—H17B109.5
C5—C6—O14120.1 (3)H17A—C17—H17C109.5
C7—C6—O14118.2 (3)H17B—C17—H17C109.5
C6—C7—C8118.9 (3)C7—O18—C19118.0 (3)
C6—C7—O18115.4 (3)O18—C19—H19A109.5
C8—C7—O18125.7 (3)O18—C19—H19B109.5
C7—C8—H8119.7O18—C19—H19C109.5
C7—C8—C8A120.5 (3)H19A—C19—H19B109.5
H8—C8—C8A119.7H19A—C19—H19C109.5
O1—C8A—C4A123.3 (3)H19B—C19—H19C109.5
C8A—O1—C2—C347.3 (4)C5—C6—C7—C80.0 (5)
C8A—O1—C2—C9167.3 (3)C5—C6—C7—O18178.8 (3)
C8A—O1—C2—C1073.9 (4)O14—C6—C7—C8174.6 (3)
O1—C2—C3—C454.9 (4)O14—C6—C7—O184.1 (5)
C9—C2—C3—C4169.1 (4)C6—C7—C8—C8A0.2 (6)
C10—C2—C3—C464.7 (5)O18—C7—C8—C8A178.4 (3)
C2—C3—C4—C4A35.2 (5)C2—O1—C8A—C4A19.1 (5)
C2—C3—C4—O11146.1 (4)C2—O1—C8A—C8161.7 (3)
C3—C4—C4A—C5171.3 (3)C7—C8—C8A—O1179.8 (3)
C3—C4—C4A—C8A5.3 (5)C7—C8—C8A—C4A0.9 (6)
O11—C4—C4A—C57.4 (6)C4—C4A—C8A—O13.8 (6)
O11—C4—C4A—C8A176.0 (4)C4—C4A—C8A—C8175.5 (3)
C4—C4A—C5—C6175.6 (3)C5—C4A—C8A—O1179.5 (3)
C4—C4A—C5—C124.3 (6)C5—C4A—C8A—C81.3 (5)
C8A—C4A—C5—C61.1 (5)C5—C6—O14—C15106.9 (4)
C8A—C4A—C5—C12179.0 (3)C7—C6—O14—C1578.4 (4)
C4A—C5—C6—C70.4 (5)C6—O14—C15—O1612.0 (6)
C4A—C5—C6—O14174.9 (3)C6—O14—C15—C17166.7 (3)
C12—C5—C6—C7179.7 (3)C6—C7—O18—C19173.1 (3)
C12—C5—C6—O145.1 (5)C8—C7—O18—C195.5 (5)
 

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