Download citation
Download citation
link to html
The title mol­ecule, C20H20N2O, is nearly planar except for the C(CH3)2 group. The disubstituted C atom is displaced by 0.635 (2) Å from the mean plane of the remaining atoms of the cyclo­hexene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018700/ya6074sup1.cif
Contains datablocks I, ccd1525

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018700/ya6074Isup2.hkl
Contains datablock I

CCDC reference: 177204

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.125
  • Data-to-parameter ratio = 18.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.073 Value of mu given = 0.070 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(7) - C(8) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(7) - C(9) = 1.43 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).

(I) top
Crystal data top
C20H20N2ODx = 1.180 Mg m3
Mr = 304.38Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 20401 reflections
a = 13.1374 (3) Åθ = 3.1–27.5°
b = 13.2089 (3) ŵ = 0.07 mm1
c = 19.7506 (4) ÅT = 291 K
V = 3427.33 (13) Å3Plate, yellow
Z = 80.5 × 0.4 × 0.1 mm
F(000) = 1296
Data collection top
Nonius KappaCCD
diffractometer
1907 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
Detector resolution: 10 vertical, 18 horizontal pixels mm-1h = 1717
198 frames via ω–rotation (Δω=1°) with 2 sets at different κ–angles and two times 10 s per frame scansk = 1717
20402 measured reflectionsl = 2525
3890 independent reflections
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.059P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
3890 reflectionsΔρmax = 0.14 e Å3
212 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: 0.0077 (9)
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
O10.46315 (10)0.23212 (9)0.72462 (6)0.0657 (4)
N10.93705 (13)0.27298 (13)0.42465 (9)0.0826 (6)
N20.61234 (14)0.32673 (13)0.43363 (8)0.0771 (5)
C10.64207 (12)0.02054 (12)0.57643 (7)0.0449 (4)
C20.65555 (12)0.09737 (12)0.53187 (7)0.0484 (4)
H2A0.59820.13090.51580.058*
C30.75271 (12)0.12940 (11)0.50843 (7)0.0435 (4)
C40.84300 (12)0.06699 (13)0.52766 (7)0.0486 (4)
H4A0.85100.01240.49530.058*
H4B0.90370.10870.52570.058*
C50.83251 (12)0.02203 (12)0.59921 (8)0.0493 (4)
C60.73255 (11)0.03647 (13)0.60289 (8)0.0538 (5)
H6A0.71980.05480.64970.065*
H6B0.73970.09870.57720.065*
C70.76302 (13)0.21379 (12)0.46917 (7)0.0466 (4)
C80.85982 (15)0.24642 (13)0.44472 (9)0.0565 (5)
C90.67828 (15)0.27521 (13)0.44927 (8)0.0541 (5)
C100.83346 (15)0.10775 (14)0.65131 (8)0.0728 (6)
H10A0.82660.07990.69600.109*
H10B0.89650.14410.64810.109*
H10C0.77780.15300.64250.109*
C110.92227 (13)0.04892 (15)0.61252 (9)0.0742 (6)
H11A0.91670.07660.65730.111*
H11B0.92160.10290.58000.111*
H11C0.98480.01180.60860.111*
C120.54031 (12)0.00338 (12)0.59807 (7)0.0492 (4)
H12A0.48840.03330.57750.059*
C130.51110 (12)0.07165 (12)0.64404 (7)0.0488 (4)
H13A0.56150.11160.66350.059*
C140.40676 (12)0.08869 (13)0.66618 (7)0.0468 (4)
C150.32710 (13)0.02411 (14)0.64868 (8)0.0573 (5)
H15A0.34140.03350.62330.069*
C160.22798 (14)0.04275 (16)0.66763 (9)0.0666 (5)
H16A0.17640.00180.65520.080*
C170.20584 (15)0.12745 (18)0.70494 (9)0.0699 (6)
H17A0.13880.14110.71700.084*
C180.28212 (15)0.19223 (16)0.72462 (8)0.0654 (5)
H18A0.26660.24930.75020.079*
C190.38256 (14)0.17281 (14)0.70640 (8)0.0519 (5)
C200.44540 (17)0.31847 (15)0.76664 (9)0.0814 (6)
H20A0.50910.35050.77700.122*
H20B0.41290.29740.80780.122*
H20C0.40220.36550.74320.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0619 (9)0.0677 (9)0.0676 (8)0.0103 (7)0.0068 (6)0.0208 (6)
N10.0646 (12)0.0794 (12)0.1037 (13)0.0184 (10)0.0111 (10)0.0235 (10)
N20.0811 (13)0.0677 (11)0.0823 (11)0.0139 (10)0.0013 (10)0.0082 (9)
C10.0404 (10)0.0466 (10)0.0476 (9)0.0030 (8)0.0057 (8)0.0000 (8)
C20.0395 (10)0.0527 (10)0.0530 (9)0.0021 (8)0.0038 (8)0.0061 (8)
C30.0448 (10)0.0442 (9)0.0416 (8)0.0027 (8)0.0055 (8)0.0030 (7)
C40.0414 (10)0.0524 (10)0.0519 (9)0.0006 (8)0.0087 (8)0.0015 (8)
C50.0362 (10)0.0600 (11)0.0516 (10)0.0018 (8)0.0041 (8)0.0062 (8)
C60.0443 (11)0.0592 (11)0.0578 (10)0.0025 (9)0.0049 (8)0.0121 (8)
C70.0464 (11)0.0441 (10)0.0492 (9)0.0044 (8)0.0053 (8)0.0001 (8)
C80.0575 (13)0.0481 (11)0.0638 (11)0.0062 (9)0.0015 (10)0.0098 (8)
C90.0608 (13)0.0470 (10)0.0546 (10)0.0020 (10)0.0060 (9)0.0039 (8)
C100.0618 (13)0.0975 (15)0.0591 (11)0.0087 (11)0.0003 (9)0.0113 (11)
C110.0466 (12)0.0922 (15)0.0837 (12)0.0099 (10)0.0044 (10)0.0296 (11)
C120.0401 (10)0.0548 (10)0.0527 (9)0.0010 (8)0.0022 (8)0.0065 (8)
C130.0427 (10)0.0541 (11)0.0497 (9)0.0051 (8)0.0002 (8)0.0033 (8)
C140.0431 (10)0.0549 (10)0.0426 (9)0.0096 (9)0.0032 (8)0.0024 (8)
C150.0482 (11)0.0671 (12)0.0565 (10)0.0040 (10)0.0063 (9)0.0000 (9)
C160.0477 (12)0.0911 (15)0.0609 (11)0.0004 (10)0.0069 (9)0.0080 (11)
C170.0460 (13)0.1059 (17)0.0577 (11)0.0175 (12)0.0121 (10)0.0129 (11)
C180.0618 (14)0.0829 (14)0.0516 (10)0.0247 (12)0.0111 (10)0.0017 (9)
C190.0493 (12)0.0625 (12)0.0438 (9)0.0103 (10)0.0027 (8)0.0010 (8)
C200.0974 (17)0.0705 (14)0.0763 (12)0.0148 (12)0.0088 (12)0.0220 (10)
Geometric parameters (Å, º) top
O1—C191.365 (2)C10—H10B0.9600
O1—C201.4296 (19)C10—H10C0.9600
N1—C81.144 (2)C11—H11A0.9600
N2—C91.144 (2)C11—H11B0.9600
C1—C21.355 (2)C11—H11C0.9600
C1—C121.439 (2)C12—C131.336 (2)
C1—C61.501 (2)C12—H12A0.9300
C2—C31.422 (2)C13—C141.456 (2)
C2—H2A0.9300C13—H13A0.9300
C3—C71.365 (2)C14—C151.394 (2)
C3—C41.494 (2)C14—C191.402 (2)
C4—C51.539 (2)C15—C161.377 (2)
C4—H4A0.9700C15—H15A0.9300
C4—H4B0.9700C16—C171.371 (3)
C5—C61.526 (2)C16—H16A0.9300
C5—C111.529 (2)C17—C181.374 (3)
C5—C101.530 (2)C17—H17A0.9300
C6—H6A0.9700C18—C191.392 (2)
C6—H6B0.9700C18—H18A0.9300
C7—C81.427 (2)C20—H20A0.9600
C7—C91.432 (3)C20—H20B0.9600
C10—H10A0.9600C20—H20C0.9600
C19—O1—C20118.96 (14)H10B—C10—H10C109.5
C2—C1—C12118.62 (14)C5—C11—H11A109.5
C2—C1—C6119.89 (14)C5—C11—H11B109.5
C12—C1—C6121.48 (14)H11A—C11—H11B109.5
C1—C2—C3123.48 (15)C5—C11—H11C109.5
C1—C2—H2A118.3H11A—C11—H11C109.5
C3—C2—H2A118.3H11B—C11—H11C109.5
C7—C3—C2121.14 (15)C13—C12—C1128.10 (15)
C7—C3—C4121.10 (14)C13—C12—H12A115.9
C2—C3—C4117.76 (14)C1—C12—H12A115.9
C3—C4—C5112.05 (12)C12—C13—C14125.37 (16)
C3—C4—H4A109.2C12—C13—H13A117.3
C5—C4—H4A109.2C14—C13—H13A117.3
C3—C4—H4B109.2C15—C14—C19117.08 (15)
C5—C4—H4B109.2C15—C14—C13122.52 (15)
H4A—C4—H4B107.9C19—C14—C13120.39 (16)
C6—C5—C11110.20 (14)C16—C15—C14122.22 (17)
C6—C5—C10110.47 (13)C16—C15—H15A118.9
C11—C5—C10109.37 (14)C14—C15—H15A118.9
C6—C5—C4108.44 (13)C17—C16—C15119.51 (18)
C11—C5—C4108.99 (13)C17—C16—H16A120.2
C10—C5—C4109.35 (13)C15—C16—H16A120.2
C1—C6—C5114.27 (13)C16—C17—C18120.37 (17)
C1—C6—H6A108.7C16—C17—H17A119.8
C5—C6—H6A108.7C18—C17—H17A119.8
C1—C6—H6B108.7C17—C18—C19120.25 (18)
C5—C6—H6B108.7C17—C18—H18A119.9
H6A—C6—H6B107.6C19—C18—H18A119.9
C3—C7—C8121.84 (15)O1—C19—C18124.16 (17)
C3—C7—C9122.78 (15)O1—C19—C14115.35 (15)
C8—C7—C9115.38 (14)C18—C19—C14120.49 (18)
N1—C8—C7179.4 (2)O1—C20—H20A109.5
N2—C9—C7178.0 (2)O1—C20—H20B109.5
C5—C10—H10A109.5H20A—C20—H20B109.5
C5—C10—H10B109.5O1—C20—H20C109.5
H10A—C10—H10B109.5H20A—C20—H20C109.5
C5—C10—H10C109.5H20B—C20—H20C109.5
H10A—C10—H10C109.5
C12—C1—C2—C3178.24 (14)C2—C1—C12—C13175.90 (15)
C6—C1—C2—C30.8 (2)C6—C1—C12—C133.2 (3)
C1—C2—C3—C7173.03 (14)C1—C12—C13—C14176.71 (15)
C1—C2—C3—C47.6 (2)C12—C13—C14—C159.9 (2)
C7—C3—C4—C5145.22 (14)C12—C13—C14—C19169.69 (15)
C2—C3—C4—C535.36 (19)C19—C14—C15—C162.2 (2)
C3—C4—C5—C654.49 (18)C13—C14—C15—C16177.47 (14)
C3—C4—C5—C11174.47 (14)C14—C15—C16—C170.1 (3)
C3—C4—C5—C1066.02 (17)C15—C16—C17—C181.4 (3)
C2—C1—C6—C523.0 (2)C16—C17—C18—C190.5 (3)
C12—C1—C6—C5156.10 (13)C20—O1—C19—C181.8 (2)
C11—C5—C6—C1167.78 (13)C20—O1—C19—C14178.91 (14)
C10—C5—C6—C171.25 (17)C17—C18—C19—O1178.94 (15)
C4—C5—C6—C148.56 (18)C17—C18—C19—C141.8 (3)
C2—C3—C7—C8179.41 (15)C15—C14—C19—O1177.62 (13)
C4—C3—C7—C80.0 (2)C13—C14—C19—O12.7 (2)
C2—C3—C7—C90.2 (2)C15—C14—C19—C183.1 (2)
C4—C3—C7—C9179.57 (14)C13—C14—C19—C18176.56 (14)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds