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In the title compound, C22H26N2, the tetra­hydro­pyrimidine ring is planar except for the C atom bearing the two methyl groups. The NH group is not involved in classical hydrogen bonding, but instead displays a contact of 2.83 Å to the midpoint of a phenyl C-C bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003209/bt6238sup1.cif
Contains datablocks 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003209/bt62383sup2.hkl
Contains datablock 3

CCDC reference: 206779

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.118
  • Data-to-parameter ratio = 14.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N3 - H03 ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

4,4-Dimethyl-2,6-diphenyl-2-(2-methyl-1-propenyl)-tetrahydropyrimidine top
Crystal data top
C22H26N2F(000) = 688
Mr = 318.45Dx = 1.160 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.268 (3) ÅCell parameters from 50 reflections
b = 8.401 (3) Åθ = 10–11.5°
c = 21.281 (7) ŵ = 0.07 mm1
β = 96.45 (3)°T = 178 K
V = 1824.1 (10) Å3Prism, pale violet
Z = 40.70 × 0.25 × 0.20 mm
Data collection top
Nicolet R3
diffractometer
Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.1°
Graphite monochromatorh = 612
ω–scank = 99
6491 measured reflectionsl = 2525
3204 independent reflections3 standard reflections every 147 reflections
2169 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0614P)2 + 0.2435P]
where P = (Fo2 + 2Fc2)/3
3204 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.18 e Å3
Special details top

Experimental. 4,4-Dimethyl-2,6-diphenyl-2-(2-methyl-1-propenyl)-tetrahydropyrimidine

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
N10.27022 (13)0.40731 (16)0.56831 (6)0.0289 (3)
C20.28283 (16)0.5028 (2)0.62662 (7)0.0290 (4)
N30.41735 (14)0.52741 (18)0.65769 (7)0.0308 (4)
H030.4507 (19)0.613 (2)0.6405 (9)0.045 (6)*
C40.51003 (16)0.3963 (2)0.65165 (8)0.0312 (4)
C50.50736 (16)0.3476 (2)0.58213 (8)0.0326 (4)
H5A0.55910.42510.56020.039*
H5B0.54920.24190.57980.039*
C60.36987 (16)0.3404 (2)0.54871 (8)0.0284 (4)
C70.47730 (19)0.2539 (2)0.69179 (9)0.0384 (5)
H7A0.46970.28940.73510.046*
H7B0.54710.17430.69230.046*
H7C0.39410.20680.67370.046*
C80.64544 (18)0.4585 (2)0.67644 (9)0.0409 (5)
H8A0.66590.55230.65200.049*
H8B0.71090.37550.67220.049*
H8C0.64660.48780.72110.049*
C90.34697 (16)0.2526 (2)0.48703 (7)0.0291 (4)
C100.22038 (18)0.2386 (2)0.45594 (8)0.0355 (4)
H100.14900.28480.47420.043*
C110.1971 (2)0.1587 (2)0.39909 (9)0.0428 (5)
H110.11020.14950.37880.051*
C120.3008 (2)0.0919 (2)0.37163 (9)0.0439 (5)
H120.28490.03670.33260.053*
C130.4268 (2)0.1060 (2)0.40123 (9)0.0418 (5)
H130.49780.06120.38230.050*
C140.45022 (18)0.1855 (2)0.45874 (8)0.0353 (4)
H140.53730.19410.47890.042*
C150.23009 (16)0.6706 (2)0.61042 (8)0.0304 (4)
C160.22381 (17)0.7806 (2)0.65914 (8)0.0355 (4)
H160.24480.74790.70180.043*
C170.18748 (18)0.9362 (2)0.64606 (9)0.0402 (5)
H170.18401.00980.67970.048*
C180.15605 (18)0.9855 (2)0.58411 (9)0.0414 (5)
H180.13231.09310.57510.050*
C190.1595 (2)0.8778 (2)0.53601 (9)0.0446 (5)
H190.13660.91080.49350.054*
C200.19611 (18)0.7204 (2)0.54862 (8)0.0381 (5)
H200.19780.64690.51480.046*
C210.20235 (17)0.4208 (2)0.67393 (8)0.0317 (4)
H210.24830.39740.71410.038*
C220.07707 (17)0.3784 (2)0.66608 (8)0.0349 (4)
C230.0154 (2)0.3007 (3)0.71933 (9)0.0486 (5)
H23A0.08260.28210.75500.058*
H23B0.02380.19900.70480.058*
H23C0.05270.37060.73270.058*
C240.01461 (18)0.4047 (2)0.60723 (9)0.0451 (5)
H24A0.08110.48320.61560.054*
H24B0.05750.30400.59400.054*
H24C0.03470.44390.57360.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0278 (8)0.0302 (8)0.0289 (7)0.0010 (6)0.0040 (6)0.0002 (6)
C20.0260 (9)0.0328 (10)0.0276 (9)0.0016 (7)0.0009 (7)0.0034 (7)
N30.0265 (8)0.0299 (8)0.0352 (8)0.0002 (7)0.0003 (6)0.0007 (7)
C40.0270 (9)0.0322 (10)0.0343 (9)0.0029 (7)0.0031 (7)0.0013 (7)
C50.0284 (9)0.0342 (10)0.0353 (10)0.0046 (8)0.0045 (7)0.0024 (8)
C60.0289 (9)0.0277 (9)0.0292 (9)0.0002 (7)0.0050 (7)0.0049 (7)
C70.0415 (11)0.0366 (10)0.0368 (10)0.0047 (9)0.0029 (8)0.0045 (8)
C80.0308 (10)0.0448 (11)0.0454 (11)0.0034 (9)0.0029 (8)0.0011 (9)
C90.0327 (10)0.0279 (9)0.0272 (9)0.0005 (7)0.0057 (7)0.0040 (7)
C100.0361 (11)0.0405 (11)0.0304 (9)0.0022 (8)0.0055 (8)0.0018 (8)
C110.0436 (11)0.0492 (12)0.0347 (10)0.0035 (10)0.0007 (8)0.0010 (9)
C120.0611 (14)0.0399 (11)0.0310 (10)0.0017 (10)0.0061 (9)0.0034 (8)
C130.0497 (13)0.0368 (11)0.0410 (11)0.0066 (9)0.0143 (9)0.0021 (9)
C140.0377 (10)0.0326 (10)0.0363 (10)0.0015 (8)0.0070 (8)0.0003 (8)
C150.0212 (9)0.0353 (10)0.0348 (10)0.0006 (7)0.0043 (7)0.0011 (8)
C160.0337 (10)0.0401 (11)0.0326 (10)0.0048 (8)0.0029 (8)0.0005 (8)
C170.0372 (11)0.0376 (11)0.0463 (11)0.0031 (9)0.0072 (9)0.0060 (9)
C180.0362 (11)0.0341 (10)0.0533 (12)0.0046 (8)0.0026 (9)0.0044 (9)
C190.0496 (12)0.0433 (12)0.0393 (11)0.0040 (10)0.0023 (9)0.0068 (9)
C200.0405 (11)0.0385 (11)0.0342 (10)0.0003 (9)0.0002 (8)0.0018 (8)
C210.0325 (10)0.0352 (10)0.0274 (9)0.0011 (8)0.0029 (7)0.0015 (7)
C220.0331 (10)0.0368 (10)0.0357 (10)0.0037 (8)0.0075 (8)0.0017 (8)
C230.0406 (12)0.0610 (14)0.0462 (12)0.0018 (10)0.0138 (9)0.0043 (10)
C240.0318 (11)0.0588 (14)0.0442 (11)0.0006 (9)0.0024 (9)0.0037 (10)
Geometric parameters (Å, º) top
N1—C61.278 (2)C12—C131.379 (3)
N1—C21.471 (2)C12—H120.9500
C2—N31.477 (2)C13—C141.391 (2)
C2—C211.535 (2)C13—H130.9500
C2—C151.536 (2)C14—H140.9500
N3—C41.471 (2)C15—C201.387 (2)
N3—H030.89 (2)C15—C161.396 (2)
C4—C81.523 (2)C16—C171.379 (3)
C4—C71.529 (2)C16—H160.9500
C4—C51.532 (2)C17—C181.385 (3)
C5—C61.509 (2)C17—H170.9500
C5—H5A0.9900C18—C191.370 (3)
C5—H5B0.9900C18—H180.9500
C6—C91.501 (2)C19—C201.392 (3)
C7—H7A0.9800C19—H190.9500
C7—H7B0.9800C20—H200.9500
C7—H7C0.9800C21—C221.327 (2)
C8—H8A0.9800C21—H210.9500
C8—H8B0.9800C22—C241.496 (3)
C8—H8C0.9800C22—C231.507 (3)
C9—C141.396 (2)C23—H23A0.9800
C9—C101.396 (3)C23—H23B0.9800
C10—C111.381 (3)C23—H23C0.9800
C10—H100.9500C24—H24A0.9800
C11—C121.389 (3)C24—H24B0.9800
C11—H110.9500C24—H24C0.9800
C6—N1—C2121.16 (14)C13—C12—C11119.81 (18)
N1—C2—N3116.31 (13)C13—C12—H12120.1
N1—C2—C21107.80 (14)C11—C12—H12120.1
N3—C2—C21108.32 (13)C12—C13—C14120.26 (18)
N1—C2—C15108.42 (13)C12—C13—H13119.9
N3—C2—C15105.08 (14)C14—C13—H13119.9
C21—C2—C15110.90 (13)C13—C14—C9120.57 (18)
C4—N3—C2115.96 (14)C13—C14—H14119.7
C4—N3—H03106.7 (13)C9—C14—H14119.7
C2—N3—H03108.2 (13)C20—C15—C16118.50 (17)
N3—C4—C8106.70 (14)C20—C15—C2122.30 (15)
N3—C4—C7110.62 (14)C16—C15—C2119.07 (15)
C8—C4—C7108.92 (15)C17—C16—C15120.78 (17)
N3—C4—C5110.04 (13)C17—C16—H16119.6
C8—C4—C5110.04 (14)C15—C16—H16119.6
C7—C4—C5110.45 (15)C16—C17—C18120.31 (17)
C6—C5—C4112.35 (14)C16—C17—H17119.8
C6—C5—H5A109.1C18—C17—H17119.8
C4—C5—H5A109.1C19—C18—C17119.37 (18)
C6—C5—H5B109.1C19—C18—H18120.3
C4—C5—H5B109.1C17—C18—H18120.3
H5A—C5—H5B107.9C18—C19—C20120.83 (18)
N1—C6—C9116.69 (15)C18—C19—H19119.6
N1—C6—C5124.71 (15)C20—C19—H19119.6
C9—C6—C5118.58 (14)C15—C20—C19120.19 (17)
C4—C7—H7A109.5C15—C20—H20119.9
C4—C7—H7B109.5C19—C20—H20119.9
H7A—C7—H7B109.5C22—C21—C2128.56 (16)
C4—C7—H7C109.5C22—C21—H21115.7
H7A—C7—H7C109.5C2—C21—H21115.7
H7B—C7—H7C109.5C21—C22—C24125.13 (17)
C4—C8—H8A109.5C21—C22—C23120.31 (17)
C4—C8—H8B109.5C24—C22—C23114.54 (16)
H8A—C8—H8B109.5C22—C23—H23A109.5
C4—C8—H8C109.5C22—C23—H23B109.5
H8A—C8—H8C109.5H23A—C23—H23B109.5
H8B—C8—H8C109.5C22—C23—H23C109.5
C14—C9—C10118.27 (16)H23A—C23—H23C109.5
C14—C9—C6121.59 (15)H23B—C23—H23C109.5
C10—C9—C6120.13 (15)C22—C24—H24A109.5
C11—C10—C9121.09 (17)C22—C24—H24B109.5
C11—C10—H10119.5H24A—C24—H24B109.5
C9—C10—H10119.5C22—C24—H24C109.5
C10—C11—C12119.99 (18)H24A—C24—H24C109.5
C10—C11—H11120.0H24B—C24—H24C109.5
C12—C11—H11120.0
C6—N1—C2—N34.9 (2)C11—C12—C13—C140.6 (3)
C6—N1—C2—C21116.87 (17)C12—C13—C14—C90.3 (3)
C6—N1—C2—C15123.01 (16)C10—C9—C14—C130.4 (3)
N1—C2—N3—C432.5 (2)C6—C9—C14—C13179.35 (16)
C21—C2—N3—C489.00 (16)N1—C2—C15—C208.3 (2)
C15—C2—N3—C4152.42 (14)N3—C2—C15—C20116.66 (17)
C2—N3—C4—C8170.15 (14)C21—C2—C15—C20126.51 (17)
C2—N3—C4—C771.52 (19)N1—C2—C15—C16175.84 (15)
C2—N3—C4—C550.80 (19)N3—C2—C15—C1659.16 (19)
N3—C4—C5—C642.63 (19)C21—C2—C15—C1657.7 (2)
C8—C4—C5—C6159.93 (15)C20—C15—C16—C171.4 (3)
C7—C4—C5—C679.78 (18)C2—C15—C16—C17174.54 (16)
C2—N1—C6—C9177.07 (14)C15—C16—C17—C180.3 (3)
C2—N1—C6—C51.2 (3)C16—C17—C18—C191.0 (3)
C4—C5—C6—N118.5 (2)C17—C18—C19—C201.0 (3)
C4—C5—C6—C9163.24 (14)C16—C15—C20—C191.4 (3)
N1—C6—C9—C14175.04 (16)C2—C15—C20—C19174.45 (17)
C5—C6—C9—C143.4 (2)C18—C19—C20—C150.2 (3)
N1—C6—C9—C103.9 (2)N1—C2—C21—C2254.2 (2)
C5—C6—C9—C10177.71 (16)N3—C2—C21—C22179.15 (17)
C14—C9—C10—C110.9 (3)C15—C2—C21—C2264.3 (2)
C6—C9—C10—C11179.83 (16)C2—C21—C22—C240.6 (3)
C9—C10—C11—C120.6 (3)C2—C21—C22—C23179.04 (17)
C10—C11—C12—C130.2 (3)
 

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