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The title compound, C20H22FNO4, was synthesized by the reaction of 4-fluoro­benz­aldehyde with 5,5-di­methyl-1,3-cyclo­hexanedione and ethyl cyano­acetate. The pyran ring adopts a boat conformation, while the fused six-membered ring adopts a distorted boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019834/ob6286sup1.cif
Contains datablocks y1331, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019834/ob6286Isup2.hkl
Contains datablock I

CCDC reference: 225767

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.114
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 = 6.44 su PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Ethyl 2-amino-7,7-dimethyl-4-(4-fluorophenyl)-5-oxo- 4H-5,6,7,8-tetrahydrobenzo[b]pyran-3-carboxylate top
Crystal data top
C20H22FNO4F(000) = 380
Mr = 359.39Dx = 1.266 Mg m3
Triclinic, P1Melting point = 433–434 K
a = 8.266 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.773 (1) ÅCell parameters from 32 reflections
c = 12.375 (2) Åθ = 3.1–15.1°
α = 81.40 (1)°µ = 0.09 mm1
β = 73.41 (1)°T = 296 K
γ = 82.15 (1)°Block, colorless
V = 942.6 (2) Å30.50 × 0.46 × 0.40 mm
Z = 2
Data collection top
Siemens P4
diffractometer
2258 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.008
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = 09
Absorption correction: ψ scan
XSCANS (Siemens, 1994)
k = 1111
Tmin = 0.937, Tmax = 0.964l = 1414
3694 measured reflections3 standard reflections every 97 reflections
3316 independent reflections intensity decay: 2.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0652P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3316 reflectionsΔρmax = 0.20 e Å3
247 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.040 (4)
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
xyzUiso*/Ueq
F0.26348 (18)0.02836 (14)0.02994 (10)0.0959 (4)
O10.52335 (14)0.30199 (12)0.46257 (10)0.0537 (3)
O20.05861 (15)0.33363 (15)0.48610 (11)0.0705 (4)
O30.36071 (15)0.58488 (12)0.16058 (10)0.0578 (4)
O40.62260 (18)0.59931 (14)0.17541 (12)0.0714 (4)
N0.7162 (2)0.4298 (2)0.34383 (17)0.0679 (5)
C10.2609 (3)0.1144 (2)0.10746 (15)0.0635 (5)
C20.1577 (3)0.2350 (2)0.11104 (15)0.0656 (5)
H20.08850.25790.06220.079*
C30.1572 (2)0.32373 (19)0.18902 (14)0.0535 (5)
H30.08620.40630.19260.064*
C40.26027 (19)0.29127 (17)0.26113 (13)0.0427 (4)
C50.3617 (2)0.16653 (19)0.25428 (15)0.0577 (5)
H50.43110.14210.30300.069*
C60.3636 (2)0.0770 (2)0.17745 (16)0.0661 (5)
H60.43300.00640.17370.079*
C70.2690 (2)0.39073 (16)0.34305 (12)0.0435 (4)
H70.18160.46880.34050.052*
C80.23388 (19)0.31915 (16)0.46263 (13)0.0433 (4)
C90.0607 (2)0.29604 (17)0.52702 (14)0.0504 (4)
C100.0321 (2)0.2297 (2)0.64819 (14)0.0623 (5)
H10A0.07310.18620.67040.075*
H10B0.01930.30170.69690.075*
C110.1757 (2)0.12029 (18)0.66739 (14)0.0557 (5)
C120.3419 (2)0.18812 (19)0.62373 (14)0.0550 (5)
H12A0.34910.24620.67890.066*
H12B0.43610.11590.61690.066*
C130.3588 (2)0.27438 (16)0.51192 (13)0.0448 (4)
C140.5571 (2)0.39857 (17)0.36789 (14)0.0487 (4)
C150.4398 (2)0.44808 (16)0.31017 (13)0.0448 (4)
C160.4868 (2)0.54921 (17)0.21232 (15)0.0522 (4)
C170.3990 (3)0.6784 (2)0.05613 (17)0.0714 (6)
H17A0.50300.64340.00410.086*
H17B0.41330.76980.07170.086*
C180.2539 (3)0.6871 (2)0.00542 (17)0.0785 (6)
H18A0.23960.59590.00820.094*
H18B0.27660.74700.06500.094*
H18C0.15230.72390.05680.094*
C190.1819 (3)0.0034 (2)0.6035 (2)0.0838 (7)
H19A0.19990.02780.52400.101*
H19B0.07660.04440.63190.101*
H19C0.27320.07120.61440.101*
C200.1477 (3)0.0712 (3)0.79358 (17)0.0851 (7)
H20A0.23650.00050.80420.102*
H20B0.04010.03380.82300.102*
H20C0.14910.14820.83310.102*
H1A0.754 (3)0.491 (2)0.2830 (18)0.082 (7)*
H1B0.775 (3)0.395 (2)0.3913 (17)0.077 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.1246 (11)0.1060 (10)0.0773 (8)0.0183 (8)0.0404 (8)0.0422 (7)
O10.0448 (7)0.0621 (8)0.0570 (7)0.0038 (5)0.0262 (6)0.0009 (6)
O20.0472 (7)0.0985 (10)0.0671 (8)0.0074 (7)0.0284 (7)0.0014 (7)
O30.0652 (8)0.0558 (7)0.0567 (7)0.0038 (6)0.0312 (6)0.0072 (6)
O40.0736 (9)0.0729 (9)0.0773 (9)0.0246 (8)0.0365 (8)0.0084 (7)
N0.0534 (10)0.0810 (12)0.0768 (12)0.0133 (9)0.0365 (9)0.0103 (10)
C10.0728 (13)0.0755 (14)0.0508 (11)0.0171 (11)0.0200 (10)0.0193 (10)
C20.0679 (13)0.0905 (15)0.0520 (11)0.0154 (11)0.0355 (10)0.0060 (10)
C30.0474 (10)0.0673 (11)0.0512 (10)0.0020 (8)0.0249 (8)0.0045 (8)
C40.0389 (9)0.0534 (10)0.0373 (8)0.0030 (7)0.0144 (7)0.0034 (7)
C50.0616 (11)0.0643 (12)0.0565 (11)0.0087 (9)0.0321 (9)0.0174 (9)
C60.0742 (13)0.0635 (12)0.0672 (12)0.0049 (10)0.0282 (11)0.0214 (10)
C70.0426 (9)0.0468 (9)0.0438 (9)0.0101 (7)0.0212 (7)0.0080 (7)
C80.0445 (9)0.0475 (9)0.0405 (9)0.0076 (7)0.0191 (7)0.0091 (7)
C90.0475 (10)0.0573 (11)0.0486 (10)0.0099 (8)0.0210 (8)0.0111 (8)
C100.0549 (11)0.0771 (13)0.0506 (10)0.0070 (9)0.0152 (9)0.0041 (9)
C110.0570 (11)0.0580 (11)0.0526 (10)0.0041 (9)0.0230 (9)0.0007 (8)
C120.0605 (11)0.0600 (11)0.0481 (10)0.0104 (9)0.0285 (9)0.0061 (8)
C130.0438 (10)0.0487 (9)0.0450 (9)0.0073 (7)0.0196 (8)0.0108 (7)
C140.0488 (10)0.0481 (10)0.0533 (10)0.0007 (8)0.0215 (8)0.0084 (8)
C150.0486 (10)0.0441 (9)0.0473 (9)0.0031 (7)0.0233 (8)0.0093 (7)
C160.0593 (12)0.0482 (10)0.0573 (11)0.0034 (9)0.0283 (9)0.0090 (8)
C170.0879 (15)0.0591 (12)0.0692 (13)0.0115 (11)0.0349 (11)0.0167 (10)
C180.0927 (16)0.0793 (14)0.0657 (13)0.0021 (12)0.0377 (12)0.0071 (11)
C190.0949 (17)0.0639 (13)0.0984 (17)0.0009 (12)0.0385 (14)0.0095 (12)
C200.0797 (15)0.1040 (17)0.0629 (13)0.0008 (13)0.0235 (11)0.0167 (12)
Geometric parameters (Å, º) top
F—C11.361 (2)C8—C91.455 (2)
O1—C131.3686 (19)C9—C101.508 (2)
O1—C141.3770 (19)C10—C111.532 (2)
O2—C91.2228 (18)C10—H10A0.9700
O3—C161.3541 (19)C10—H10B0.9700
O3—C171.449 (2)C11—C201.524 (2)
O4—C161.224 (2)C11—C191.528 (3)
N—C141.330 (2)C11—C121.528 (3)
N—H1A0.90 (2)C12—C131.489 (2)
N—H1B0.87 (2)C12—H12A0.9700
C1—C21.355 (3)C12—H12B0.9700
C1—C61.358 (3)C14—C151.359 (2)
C2—C31.389 (3)C15—C161.440 (2)
C2—H20.9300C17—C181.491 (3)
C3—C41.378 (2)C17—H17A0.9700
C3—H30.9300C17—H17B0.9700
C4—C51.381 (2)C18—H18A0.9600
C4—C71.528 (2)C18—H18B0.9600
C5—C61.381 (2)C18—H18C0.9600
C5—H50.9300C19—H19A0.9600
C6—H60.9300C19—H19B0.9600
C7—C81.505 (2)C19—H19C0.9600
C7—C151.514 (2)C20—H20A0.9600
C7—H70.9800C20—H20B0.9600
C8—C131.336 (2)C20—H20C0.9600
C13—O1—C14118.45 (12)C19—C11—C10109.48 (16)
C16—O3—C17116.44 (14)C12—C11—C10107.93 (15)
C14—N—H1A118.4 (14)C13—C12—C11113.27 (13)
C14—N—H1B117.9 (13)C13—C12—H12A108.9
H1A—N—H1B123 (2)C11—C12—H12A108.9
C2—C1—C6122.41 (17)C13—C12—H12B108.9
C2—C1—F118.89 (18)C11—C12—H12B108.9
C6—C1—F118.69 (19)H12A—C12—H12B107.7
C1—C2—C3118.82 (17)C8—C13—O1122.85 (14)
C1—C2—H2120.6C8—C13—C12126.18 (16)
C3—C2—H2120.6O1—C13—C12110.97 (13)
C4—C3—C2121.03 (17)N—C14—C15127.79 (18)
C4—C3—H3119.5N—C14—O1109.95 (15)
C2—C3—H3119.5C15—C14—O1122.24 (15)
C3—C4—C5117.61 (15)C14—C15—C16118.16 (15)
C3—C4—C7121.98 (15)C14—C15—C7120.74 (15)
C5—C4—C7120.37 (13)C16—C15—C7120.96 (13)
C6—C5—C4122.10 (16)O4—C16—O3121.38 (16)
C6—C5—H5118.9O4—C16—C15126.82 (15)
C4—C5—H5118.9O3—C16—C15111.79 (15)
C1—C6—C5118.02 (18)O3—C17—C18107.42 (16)
C1—C6—H6121.0O3—C17—H17A110.2
C5—C6—H6121.0C18—C17—H17A110.2
C8—C7—C15109.62 (12)O3—C17—H17B110.2
C8—C7—C4110.61 (13)C18—C17—H17B110.2
C15—C7—C4111.66 (13)H17A—C17—H17B108.5
C8—C7—H7108.3C17—C18—H18A109.5
C15—C7—H7108.3C17—C18—H18B109.5
C4—C7—H7108.3H18A—C18—H18B109.5
C13—C8—C9118.44 (14)C17—C18—H18C109.5
C13—C8—C7121.56 (15)H18A—C18—H18C109.5
C9—C8—C7120.00 (13)H18B—C18—H18C109.5
O2—C9—C8121.42 (15)C11—C19—H19A109.5
O2—C9—C10120.83 (16)C11—C19—H19B109.5
C8—C9—C10117.70 (14)H19A—C19—H19B109.5
C9—C10—C11113.66 (15)C11—C19—H19C109.5
C9—C10—H10A108.8H19A—C19—H19C109.5
C11—C10—H10A108.8H19B—C19—H19C109.5
C9—C10—H10B108.8C11—C20—H20A109.5
C11—C10—H10B108.8C11—C20—H20B109.5
H10A—C10—H10B107.7H20A—C20—H20B109.5
C20—C11—C19109.62 (17)C11—C20—H20C109.5
C20—C11—C12108.76 (15)H20A—C20—H20C109.5
C19—C11—C12110.67 (16)H20B—C20—H20C109.5
C20—C11—C10110.36 (16)
C6—C1—C2—C30.1 (3)C19—C11—C12—C1375.76 (18)
F—C1—C2—C3178.99 (16)C10—C11—C12—C1344.02 (19)
C1—C2—C3—C40.5 (3)C9—C8—C13—O1173.96 (14)
C2—C3—C4—C51.0 (3)C7—C8—C13—O16.6 (2)
C2—C3—C4—C7176.61 (16)C9—C8—C13—C127.1 (2)
C3—C4—C5—C60.9 (3)C7—C8—C13—C12172.29 (15)
C7—C4—C5—C6176.77 (16)C14—O1—C13—C811.2 (2)
C2—C1—C6—C50.3 (3)C14—O1—C13—C12169.72 (14)
F—C1—C6—C5178.86 (16)C11—C12—C13—C815.1 (2)
C4—C5—C6—C10.3 (3)C11—C12—C13—O1163.89 (13)
C3—C4—C7—C8125.76 (16)C13—O1—C14—N169.07 (14)
C5—C4—C7—C856.7 (2)C13—O1—C14—C1512.2 (2)
C3—C4—C7—C15111.87 (17)N—C14—C15—C161.7 (3)
C5—C4—C7—C1565.70 (19)O1—C14—C15—C16179.83 (14)
C15—C7—C8—C1320.8 (2)N—C14—C15—C7174.03 (17)
C4—C7—C8—C13102.72 (17)O1—C14—C15—C74.4 (2)
C15—C7—C8—C9159.77 (13)C8—C7—C15—C1419.6 (2)
C4—C7—C8—C976.68 (17)C4—C7—C15—C14103.32 (17)
C13—C8—C9—O2179.39 (16)C8—C7—C15—C16164.78 (14)
C7—C8—C9—O20.0 (2)C4—C7—C15—C1672.29 (18)
C13—C8—C9—C103.3 (2)C17—O3—C16—O43.6 (2)
C7—C8—C9—C10177.29 (15)C17—O3—C16—C15175.58 (15)
O2—C9—C10—C11147.31 (17)C14—C15—C16—O41.7 (3)
C8—C9—C10—C1135.4 (2)C7—C15—C16—O4177.39 (16)
C9—C10—C11—C20173.18 (17)C14—C15—C16—O3177.44 (14)
C9—C10—C11—C1966.1 (2)C7—C15—C16—O31.7 (2)
C9—C10—C11—C1254.4 (2)C16—O3—C17—C18171.88 (16)
C20—C11—C12—C13163.76 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1B···O2i0.87 (2)2.03 (2)2.889 (2)170.6 (19)
N—H1A···O40.90 (2)2.04 (2)2.688 (2)128.1 (18)
Symmetry code: (i) x+1, y, z.
 

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