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The title compound, C14H18N2O2, which was obtained from an extended Biginelli reaction, contains a pyran ring with a chair conformation, a pyrimidine ring with a half-chair conformation and a benzene ring. The crystal structure is stabilized by an intermolecular hydrogen-bond network involving both NH groups and the carbonyl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008147/jh6001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008147/jh6001Isup2.hkl
Contains datablock I

CCDC reference: 270462

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.112
  • 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 ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT707_ALERT_1_C D...A Calc 3.1150(17), Rep 3.1177(16), Dev.. 1.59 Sigma N1 -O 1.555 2.755 PLAT728_ALERT_1_C D-H..A Calc 177.61, Rep 176.00 Dev... 1.61 Deg. N1 -H1 -O 1.555 1.555 2.755
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

4-p-Tolyl-1,3,4,4a,5,6,7,8a-octahydro-2H-pyrano[2,3-d]pyrimidin-2-one top
Crystal data top
C14H18N2O2Z = 2
Mr = 246.30F(000) = 264
Triclinic, P1Dx = 1.322 Mg m3
a = 7.7151 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.5541 (11) ÅCell parameters from 1671 reflections
c = 9.6887 (13) Åθ = 2.7–28.4°
α = 88.516 (2)°µ = 0.09 mm1
β = 76.964 (2)°T = 293 K
γ = 83.401 (2)°Prism, colourless
V = 618.81 (14) Å30.34 × 0.34 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1865 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.3°, θmin = 2.2°
φ and ω scansh = 89
3223 measured reflectionsk = 610
2204 independent reflectionsl = 1111
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.0889P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
2204 reflectionsΔρmax = 0.20 e Å3
164 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (7)
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*/UeqOcc. (<1)
O0.75791 (14)0.03244 (11)0.00243 (11)0.0486 (3)
O80.78614 (12)0.44337 (10)0.02673 (9)0.0358 (3)
N10.84457 (15)0.18026 (13)0.08654 (13)0.0413 (3)
H10.95460.13990.06590.050*
N30.54593 (15)0.14422 (14)0.12559 (13)0.0414 (3)
H30.46620.08640.11410.050*
C20.71710 (18)0.09202 (15)0.06612 (14)0.0362 (3)
C40.48082 (17)0.28861 (15)0.20754 (13)0.0331 (3)
H40.43490.36780.14590.040*
C50.58620 (19)0.52325 (16)0.30750 (14)0.0393 (3)
H5A0.46730.53490.36890.047*
H5B0.66990.54920.36220.047*
C60.59077 (19)0.63768 (16)0.18378 (15)0.0405 (4)
H6A0.49080.62740.14050.049*
H6B0.57980.74480.21780.049*
C70.76487 (18)0.60300 (16)0.07525 (15)0.0377 (3)
H7A0.76600.67410.00450.045*
H7B0.86420.62020.11700.045*
C90.80411 (17)0.33677 (15)0.14062 (14)0.0337 (3)
H90.90380.36260.17990.040*
C100.63427 (17)0.35172 (15)0.25793 (13)0.0330 (3)
H100.65790.28750.33830.040*
C110.32813 (17)0.25735 (16)0.33050 (14)0.0355 (3)
C120.3511 (2)0.1457 (2)0.4312 (2)0.0652 (5)
H120.46190.08640.42230.078*
C130.2139 (2)0.1188 (2)0.5454 (2)0.0686 (6)
H130.23560.04410.61260.082*
C140.0466 (2)0.2000 (2)0.56179 (16)0.0491 (4)
C150.0227 (2)0.3106 (2)0.46006 (17)0.0524 (4)
H150.08950.36700.46750.063*
C160.16138 (19)0.34086 (19)0.34634 (15)0.0442 (4)
H160.14110.41800.28060.053*
C170.1023 (3)0.1706 (3)0.6870 (2)0.0740 (6)
H17A0.20890.23760.68050.089*0.50
H17B0.06800.19300.77300.089*0.50
H17C0.12480.06250.68710.089*0.50
H17D0.05890.09120.74660.089*0.50
H17E0.19980.13570.65400.089*0.50
H17F0.14300.26620.74000.089*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0464 (6)0.0341 (6)0.0583 (7)0.0079 (4)0.0058 (5)0.0110 (5)
O80.0349 (5)0.0367 (5)0.0337 (5)0.0067 (4)0.0016 (4)0.0014 (4)
N10.0271 (6)0.0343 (6)0.0590 (8)0.0006 (5)0.0030 (5)0.0076 (5)
N30.0324 (6)0.0415 (7)0.0477 (7)0.0111 (5)0.0012 (5)0.0124 (5)
C20.0371 (7)0.0311 (7)0.0366 (7)0.0067 (6)0.0010 (6)0.0007 (6)
C40.0311 (7)0.0340 (7)0.0321 (7)0.0036 (5)0.0026 (5)0.0005 (5)
C50.0410 (8)0.0414 (8)0.0337 (7)0.0065 (6)0.0027 (6)0.0068 (6)
C60.0402 (8)0.0327 (7)0.0457 (8)0.0026 (6)0.0039 (6)0.0037 (6)
C70.0378 (7)0.0341 (7)0.0403 (7)0.0081 (6)0.0048 (6)0.0015 (6)
C90.0289 (7)0.0335 (7)0.0392 (7)0.0048 (5)0.0079 (5)0.0019 (6)
C100.0340 (7)0.0356 (7)0.0292 (7)0.0045 (5)0.0067 (5)0.0030 (5)
C110.0311 (7)0.0364 (7)0.0365 (7)0.0053 (5)0.0015 (6)0.0019 (6)
C120.0410 (9)0.0664 (11)0.0716 (12)0.0105 (8)0.0105 (8)0.0312 (9)
C130.0549 (10)0.0727 (12)0.0641 (11)0.0006 (9)0.0084 (9)0.0324 (10)
C140.0411 (8)0.0589 (10)0.0434 (8)0.0131 (7)0.0031 (7)0.0053 (7)
C150.0300 (7)0.0724 (11)0.0509 (9)0.0001 (7)0.0028 (7)0.0062 (8)
C160.0348 (8)0.0578 (9)0.0391 (8)0.0024 (6)0.0078 (6)0.0027 (7)
C170.0584 (11)0.0975 (15)0.0560 (11)0.0224 (10)0.0152 (9)0.0029 (10)
Geometric parameters (Å, º) top
O—C21.2405 (16)C9—C101.5239 (18)
O8—C91.4339 (16)C9—H90.9800
O8—C71.4351 (15)C10—H100.9800
N1—C21.3573 (18)C11—C121.373 (2)
N1—C91.4251 (17)C11—C161.3763 (19)
N1—H10.8600C12—C131.382 (2)
N3—C21.3453 (17)C12—H120.9300
N3—C41.4617 (16)C13—C141.371 (2)
N3—H30.8600C13—H130.9300
C4—C111.5170 (17)C14—C151.377 (2)
C4—C101.5339 (18)C14—C171.509 (2)
C4—H40.9800C15—C161.394 (2)
C5—C61.5246 (19)C15—H150.9300
C5—C101.5337 (18)C16—H160.9300
C5—H5A0.9700C17—H17A0.9600
C5—H5B0.9700C17—H17B0.9600
C6—C71.5117 (19)C17—H17C0.9600
C6—H6A0.9700C17—H17D0.9600
C6—H6B0.9700C17—H17E0.9600
C7—H7A0.9700C17—H17F0.9600
C7—H7B0.9700
C9—O8—C7110.14 (9)C9—C10—H10108.1
C2—N1—C9122.91 (11)C5—C10—H10108.1
C2—N1—H1118.5C4—C10—H10108.1
C9—N1—H1118.5C12—C11—C16117.32 (13)
C2—N3—C4127.05 (11)C12—C11—C4121.38 (12)
C2—N3—H3116.5C16—C11—C4121.30 (12)
C4—N3—H3116.5C11—C12—C13121.81 (15)
O—C2—N3121.86 (12)C11—C12—H12119.1
O—C2—N1121.11 (12)C13—C12—H12119.1
N3—C2—N1117.01 (11)C14—C13—C12121.52 (16)
N3—C4—C11109.56 (10)C14—C13—H13119.2
N3—C4—C10110.36 (10)C12—C13—H13119.2
C11—C4—C10111.83 (10)C13—C14—C15116.75 (14)
N3—C4—H4108.3C13—C14—C17121.27 (17)
C11—C4—H4108.3C15—C14—C17121.97 (16)
C10—C4—H4108.3C14—C15—C16122.07 (14)
C6—C5—C10112.17 (11)C14—C15—H15119.0
C6—C5—H5A109.2C16—C15—H15119.0
C10—C5—H5A109.2C11—C16—C15120.50 (14)
C6—C5—H5B109.2C11—C16—H16119.7
C10—C5—H5B109.2C15—C16—H16119.7
H5A—C5—H5B107.9C14—C17—H17A109.5
C7—C6—C5109.74 (11)C14—C17—H17B109.5
C7—C6—H6A109.7H17A—C17—H17B109.5
C5—C6—H6A109.7C14—C17—H17C109.5
C7—C6—H6B109.7H17A—C17—H17C109.5
C5—C6—H6B109.7H17B—C17—H17C109.5
H6A—C6—H6B108.2C14—C17—H17D109.5
O8—C7—C6110.59 (10)H17A—C17—H17D141.1
O8—C7—H7A109.5H17B—C17—H17D56.3
C6—C7—H7A109.5H17C—C17—H17D56.3
O8—C7—H7B109.5C14—C17—H17E109.5
C6—C7—H7B109.5H17A—C17—H17E56.3
H7A—C7—H7B108.1H17B—C17—H17E141.1
N1—C9—O8109.06 (10)H17C—C17—H17E56.3
N1—C9—C10110.93 (11)H17D—C17—H17E109.5
O8—C9—C10110.95 (10)C14—C17—H17F109.5
N1—C9—H9108.6H17A—C17—H17F56.3
O8—C9—H9108.6H17B—C17—H17F56.3
C10—C9—H9108.6H17C—C17—H17F141.1
C9—C10—C5110.04 (11)H17D—C17—H17F109.5
C9—C10—C4110.39 (10)H17E—C17—H17F109.5
C5—C10—C4111.88 (11)
C4—N3—C2—O179.54 (12)N3—C4—C10—C941.28 (14)
C4—N3—C2—N11.6 (2)C11—C4—C10—C9163.51 (11)
C9—N1—C2—O167.84 (13)N3—C4—C10—C5164.20 (10)
C9—N1—C2—N313.3 (2)C11—C4—C10—C573.58 (14)
C2—N3—C4—C11141.01 (14)N3—C4—C11—C1259.02 (18)
C2—N3—C4—C1017.46 (18)C10—C4—C11—C1263.67 (18)
C10—C5—C6—C749.78 (15)N3—C4—C11—C16121.59 (14)
C9—O8—C7—C665.38 (13)C10—C4—C11—C16115.73 (14)
C5—C6—C7—O857.64 (15)C16—C11—C12—C130.9 (3)
C2—N1—C9—O882.99 (15)C4—C11—C12—C13178.48 (17)
C2—N1—C9—C1039.50 (17)C11—C12—C13—C141.7 (3)
C7—O8—C9—N1173.70 (10)C12—C13—C14—C150.8 (3)
C7—O8—C9—C1063.82 (12)C12—C13—C14—C17179.7 (2)
N1—C9—C10—C5176.15 (10)C13—C14—C15—C160.7 (3)
O8—C9—C10—C554.76 (13)C17—C14—C15—C16178.27 (16)
N1—C9—C10—C452.16 (14)C12—C11—C16—C150.5 (2)
O8—C9—C10—C469.22 (13)C4—C11—C16—C15179.94 (13)
C6—C5—C10—C948.38 (15)C14—C15—C16—C111.3 (2)
C6—C5—C10—C474.73 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Oi0.862.263.1177 (16)176
N3—H3···Oii0.862.333.1096 (16)151
Symmetry codes: (i) x+2, y, z; (ii) x+1, y, z.
 

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