In the title compound, C
17H
21NO
3, the cyclohexene ring adopts an envelope conformation. The phenyl ring forms a dihedral angle of 35.77 (4)° with the amide plane. In the crystal, the symmetry-related molecules are linked through N—H
O, O—H
O and weak C—H
O hydrogen bonds, to form molecular networks parallel to (110).
Supporting information
CCDC reference: 206750
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.127
- Data-to-parameter ratio = 20.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
5,5'-dimethyl-2-(4-methylphenylaminocarbomethyl)-1,3-cyclohexanedione
top
Crystal data top
C17H21NO3 | F(000) = 616 |
Mr = 287.35 | Dx = 1.210 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5446 reflections |
a = 10.1239 (1) Å | θ = 2.0–28.2° |
b = 5.8366 (1) Å | µ = 0.08 mm−1 |
c = 26.9176 (1) Å | T = 293 K |
β = 97.403 (1)° | Block, colourless |
V = 1577.28 (3) Å3 | 0.48 × 0.34 × 0.26 mm |
Z = 4 | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 2972 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 28.3°, θmin = 1.5° |
ω scans | h = −13→13 |
10433 measured reflections | k = −6→7 |
3912 independent reflections | l = −35→30 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0589P)2 + 0.2846P] where P = (Fo2 + 2Fc2)/3 |
3912 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.42145 (10) | 0.7722 (2) | 0.18838 (4) | 0.0646 (4) | |
O2 | 0.64846 (11) | 0.8907 (2) | 0.29964 (5) | 0.0702 (4) | |
O3 | 0.30067 (9) | 0.36982 (18) | 0.27417 (4) | 0.0464 (3) | |
H3O | 0.2292 | 0.3458 | 0.2845 | 0.070* | |
N1 | 0.62787 (10) | 0.6838 (2) | 0.17272 (4) | 0.0423 (3) | |
H1N | 0.6977 | 0.6034 | 0.1823 | 0.051* | |
C1 | 0.63017 (12) | 0.8209 (2) | 0.12927 (5) | 0.0403 (3) | |
C2 | 0.69852 (14) | 0.7394 (3) | 0.09149 (5) | 0.0472 (3) | |
H2 | 0.7386 | 0.5958 | 0.0945 | 0.057* | |
C3 | 0.70730 (15) | 0.8712 (3) | 0.04929 (6) | 0.0544 (4) | |
H3 | 0.7544 | 0.8150 | 0.0244 | 0.065* | |
C4 | 0.64782 (15) | 1.0843 (3) | 0.04320 (6) | 0.0533 (4) | |
C5 | 0.57921 (16) | 1.1616 (3) | 0.08113 (7) | 0.0581 (4) | |
H5 | 0.5374 | 1.3036 | 0.0777 | 0.070* | |
C6 | 0.57085 (15) | 1.0342 (3) | 0.12397 (6) | 0.0523 (4) | |
H6 | 0.5254 | 1.0921 | 0.1491 | 0.063* | |
C7 | 0.6594 (2) | 1.2274 (4) | −0.00282 (7) | 0.0763 (6) | |
H7A | 0.6245 | 1.1431 | −0.0322 | 0.114* | 0.50 |
H7B | 0.7513 | 1.2635 | −0.0043 | 0.114* | 0.50 |
H7C | 0.6096 | 1.3666 | −0.0012 | 0.114* | 0.50 |
H7D | 0.6991 | 1.3724 | 0.0071 | 0.114* | 0.50 |
H7E | 0.5723 | 1.2520 | −0.0208 | 0.114* | 0.50 |
H7F | 0.7140 | 1.1488 | −0.0240 | 0.114* | 0.50 |
C8 | 0.52657 (12) | 0.6685 (2) | 0.20012 (5) | 0.0397 (3) | |
C9 | 0.54615 (12) | 0.5127 (2) | 0.24532 (5) | 0.0394 (3) | |
H9A | 0.5071 | 0.3641 | 0.2366 | 0.047* | |
H9B | 0.6406 | 0.4912 | 0.2559 | 0.047* | |
C10 | 0.48195 (11) | 0.6146 (2) | 0.28767 (5) | 0.0345 (3) | |
C11 | 0.54351 (13) | 0.8149 (3) | 0.31184 (5) | 0.0444 (3) | |
C12 | 0.47275 (16) | 0.9387 (3) | 0.34964 (6) | 0.0552 (4) | |
H12A | 0.4156 | 1.0549 | 0.3324 | 0.066* | |
H12B | 0.5385 | 1.0162 | 0.3732 | 0.066* | |
C13 | 0.38838 (13) | 0.7842 (2) | 0.37889 (5) | 0.0434 (3) | |
C14 | 0.29616 (12) | 0.6464 (2) | 0.34088 (5) | 0.0395 (3) | |
H14A | 0.2554 | 0.5254 | 0.3584 | 0.047* | |
H14B | 0.2254 | 0.7460 | 0.3258 | 0.047* | |
C15 | 0.36369 (11) | 0.5415 (2) | 0.30016 (4) | 0.0337 (3) | |
C16 | 0.30472 (19) | 0.9308 (3) | 0.41020 (7) | 0.0667 (5) | |
H16A | 0.2519 | 0.8330 | 0.4285 | 0.100* | |
H16B | 0.2472 | 1.0291 | 0.3885 | 0.100* | |
H16C | 0.3626 | 1.0225 | 0.4333 | 0.100* | |
C17 | 0.47746 (19) | 0.6245 (4) | 0.41353 (6) | 0.0714 (5) | |
H17A | 0.5301 | 0.5323 | 0.3940 | 0.107* | |
H17B | 0.4231 | 0.5270 | 0.4312 | 0.107* | |
H17C | 0.5352 | 0.7140 | 0.4371 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0364 (5) | 0.0968 (9) | 0.0649 (7) | 0.0286 (5) | 0.0228 (5) | 0.0312 (6) |
O2 | 0.0518 (6) | 0.0775 (8) | 0.0862 (8) | −0.0345 (6) | 0.0277 (6) | −0.0169 (7) |
O3 | 0.0357 (5) | 0.0542 (6) | 0.0518 (6) | −0.0147 (4) | 0.0157 (4) | −0.0157 (5) |
N1 | 0.0317 (5) | 0.0515 (7) | 0.0464 (6) | 0.0109 (5) | 0.0159 (4) | 0.0092 (5) |
C1 | 0.0327 (6) | 0.0473 (7) | 0.0426 (7) | 0.0011 (5) | 0.0119 (5) | 0.0044 (6) |
C2 | 0.0420 (7) | 0.0531 (8) | 0.0493 (8) | 0.0047 (6) | 0.0166 (6) | 0.0012 (6) |
C3 | 0.0525 (8) | 0.0697 (10) | 0.0444 (8) | −0.0083 (8) | 0.0191 (6) | −0.0015 (7) |
C4 | 0.0482 (8) | 0.0618 (10) | 0.0499 (8) | −0.0147 (7) | 0.0064 (6) | 0.0101 (7) |
C5 | 0.0571 (9) | 0.0481 (9) | 0.0709 (10) | 0.0011 (7) | 0.0158 (8) | 0.0127 (8) |
C6 | 0.0545 (8) | 0.0487 (8) | 0.0578 (9) | 0.0059 (7) | 0.0232 (7) | 0.0044 (7) |
C7 | 0.0820 (13) | 0.0866 (14) | 0.0600 (10) | −0.0224 (11) | 0.0086 (9) | 0.0231 (10) |
C8 | 0.0290 (6) | 0.0502 (8) | 0.0417 (7) | 0.0064 (5) | 0.0114 (5) | 0.0026 (6) |
C9 | 0.0299 (6) | 0.0449 (7) | 0.0455 (7) | 0.0040 (5) | 0.0130 (5) | 0.0032 (6) |
C10 | 0.0282 (5) | 0.0381 (6) | 0.0385 (6) | −0.0010 (5) | 0.0088 (4) | 0.0018 (5) |
C11 | 0.0365 (6) | 0.0461 (8) | 0.0519 (8) | −0.0101 (6) | 0.0102 (5) | −0.0002 (6) |
C12 | 0.0535 (8) | 0.0467 (8) | 0.0680 (10) | −0.0137 (7) | 0.0174 (7) | −0.0150 (7) |
C13 | 0.0420 (7) | 0.0478 (8) | 0.0414 (7) | −0.0033 (6) | 0.0086 (5) | −0.0077 (6) |
C14 | 0.0323 (6) | 0.0484 (7) | 0.0396 (6) | −0.0041 (5) | 0.0117 (5) | −0.0037 (6) |
C15 | 0.0295 (5) | 0.0372 (6) | 0.0349 (6) | −0.0020 (5) | 0.0059 (4) | −0.0008 (5) |
C16 | 0.0702 (11) | 0.0729 (11) | 0.0608 (10) | −0.0030 (9) | 0.0230 (8) | −0.0235 (9) |
C17 | 0.0717 (11) | 0.0903 (14) | 0.0487 (9) | 0.0107 (10) | −0.0062 (8) | 0.0001 (9) |
Geometric parameters (Å, º) top
O1—C8 | 1.229 (2) | C7—H7F | 0.96 |
O2—C11 | 1.234 (2) | C8—C9 | 1.511 (2) |
O3—C15 | 1.336 (2) | C9—C10 | 1.506 (2) |
O3—H3O | 0.82 | C9—H9A | 0.97 |
N1—C8 | 1.341 (2) | C9—H9B | 0.97 |
N1—C1 | 1.420 (2) | C10—C15 | 1.354 (2) |
N1—H1N | 0.86 | C10—C11 | 1.440 (2) |
C1—C6 | 1.381 (2) | C11—C12 | 1.503 (2) |
C1—C2 | 1.3859 (18) | C12—C13 | 1.528 (2) |
C2—C3 | 1.384 (2) | C12—H12A | 0.97 |
C2—H2 | 0.93 | C12—H12B | 0.97 |
C3—C4 | 1.382 (2) | C13—C14 | 1.523 (2) |
C3—H3 | 0.93 | C13—C17 | 1.528 (2) |
C4—C5 | 1.382 (2) | C13—C16 | 1.531 (2) |
C4—C7 | 1.511 (2) | C14—C15 | 1.496 (2) |
C5—C6 | 1.384 (2) | C14—H14A | 0.97 |
C5—H5 | 0.93 | C14—H14B | 0.97 |
C6—H6 | 0.93 | C16—H16A | 0.96 |
C7—H7A | 0.96 | C16—H16B | 0.96 |
C7—H7B | 0.96 | C16—H16C | 0.96 |
C7—H7C | 0.96 | C17—H17A | 0.96 |
C7—H7D | 0.96 | C17—H17B | 0.96 |
C7—H7E | 0.96 | C17—H17C | 0.96 |
| | | |
C15—O3—H3O | 109.5 | C10—C9—C8 | 110.33 (10) |
C8—N1—C1 | 125.8 (1) | C10—C9—H9A | 109.6 |
C8—N1—H1N | 117.1 | C8—C9—H9A | 109.6 |
C1—N1—H1N | 117.1 | C10—C9—H9B | 109.6 |
C6—C1—C2 | 119.03 (13) | C8—C9—H9B | 109.6 |
C6—C1—N1 | 122.67 (12) | H9A—C9—H9B | 108.1 |
C2—C1—N1 | 118.27 (12) | C15—C10—C11 | 119.28 (11) |
C3—C2—C1 | 120.15 (14) | C15—C10—C9 | 123.05 (11) |
C3—C2—H2 | 119.9 | C11—C10—C9 | 117.30 (11) |
C1—C2—H2 | 119.9 | O2—C11—C10 | 120.5 (1) |
C4—C3—C2 | 121.61 (14) | O2—C11—C12 | 120.7 (1) |
C4—C3—H3 | 119.2 | C10—C11—C12 | 118.7 (1) |
C2—C3—H3 | 119.2 | C11—C12—C13 | 114.34 (12) |
C3—C4—C5 | 117.30 (14) | C11—C12—H12A | 108.7 |
C3—C4—C7 | 121.07 (16) | C13—C12—H12A | 108.7 |
C5—C4—C7 | 121.62 (17) | C11—C12—H12B | 108.7 |
C4—C5—C6 | 122.05 (15) | C13—C12—H12B | 108.7 |
C4—C5—H5 | 119.0 | H12A—C12—H12B | 107.6 |
C6—C5—H5 | 119.0 | C14—C13—C17 | 110.53 (13) |
C1—C6—C5 | 119.83 (14) | C14—C13—C12 | 107.48 (11) |
C1—C6—H6 | 120.1 | C17—C13—C12 | 110.43 (14) |
C5—C6—H6 | 120.1 | C14—C13—C16 | 109.29 (12) |
C4—C7—H7A | 109.5 | C17—C13—C16 | 109.27 (13) |
C4—C7—H7B | 109.5 | C12—C13—C16 | 109.83 (13) |
H7A—C7—H7B | 109.5 | C15—C14—C13 | 114.21 (10) |
C4—C7—H7C | 109.5 | C15—C14—H14A | 108.7 |
H7A—C7—H7C | 109.5 | C13—C14—H14A | 108.7 |
H7B—C7—H7C | 109.5 | C15—C14—H14B | 108.7 |
C4—C7—H7D | 109.5 | C13—C14—H14B | 108.7 |
H7A—C7—H7D | 141.1 | H14A—C14—H14B | 107.6 |
H7B—C7—H7D | 56.3 | O3—C15—C10 | 119.0 (1) |
H7C—C7—H7D | 56.3 | O3—C15—C14 | 117.3 (1) |
C4—C7—H7E | 109.5 | C10—C15—C14 | 123.7 (1) |
H7A—C7—H7E | 56.3 | C13—C16—H16A | 109.5 |
H7B—C7—H7E | 141.1 | C13—C16—H16B | 109.5 |
H7C—C7—H7E | 56.3 | H16A—C16—H16B | 109.5 |
H7D—C7—H7E | 109.5 | C13—C16—H16C | 109.5 |
C4—C7—H7F | 109.5 | H16A—C16—H16C | 109.5 |
H7A—C7—H7F | 56.3 | H16B—C16—H16C | 109.5 |
H7B—C7—H7F | 56.3 | C13—C17—H17A | 109.5 |
H7C—C7—H7F | 141.1 | C13—C17—H17B | 109.5 |
H7D—C7—H7F | 109.5 | H17A—C17—H17B | 109.5 |
H7E—C7—H7F | 109.5 | C13—C17—H17C | 109.5 |
O1—C8—N1 | 121.58 (12) | H17A—C17—H17C | 109.5 |
O1—C8—C9 | 121.49 (11) | H17B—C17—H17C | 109.5 |
N1—C8—C9 | 116.91 (11) | | |
| | | |
C8—N1—C1—C6 | 36.0 (2) | C15—C10—C11—O2 | −176.95 (14) |
C8—N1—C1—C2 | −146.13 (15) | C9—C10—C11—O2 | −3.7 (2) |
C6—C1—C2—C3 | 0.3 (2) | C15—C10—C11—C12 | −1.0 (2) |
N1—C1—C2—C3 | −177.69 (13) | C9—C10—C11—C12 | 172.24 (12) |
C1—C2—C3—C4 | −0.8 (2) | O2—C11—C12—C13 | −152.64 (15) |
C2—C3—C4—C5 | 0.2 (2) | C10—C11—C12—C13 | 31.5 (2) |
C2—C3—C4—C7 | 179.4 (2) | C11—C12—C13—C14 | −52.58 (17) |
C3—C4—C5—C6 | 0.8 (2) | C11—C12—C13—C17 | 68.05 (17) |
C7—C4—C5—C6 | −178.4 (2) | C11—C12—C13—C16 | −171.38 (13) |
C2—C1—C6—C5 | 0.7 (2) | C17—C13—C14—C15 | −73.97 (16) |
N1—C1—C6—C5 | 178.56 (14) | C12—C13—C14—C15 | 46.60 (16) |
C4—C5—C6—C1 | −1.2 (3) | C16—C13—C14—C15 | 165.74 (13) |
C1—N1—C8—O1 | 2.1 (2) | C11—C10—C15—O3 | 173.40 (12) |
C1—N1—C8—C9 | −179.52 (12) | C9—C10—C15—O3 | 0.52 (19) |
O1—C8—C9—C10 | −38.60 (18) | C11—C10—C15—C14 | −4.8 (2) |
N1—C8—C9—C10 | 143.1 (1) | C9—C10—C15—C14 | −177.68 (11) |
C8—C9—C10—C15 | 102.62 (14) | C13—C14—C15—O3 | 161.75 (12) |
C8—C9—C10—C11 | −70.39 (15) | C13—C14—C15—C10 | −20.02 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.45 | 2.8824 (18) | 109 |
C9—H9A···O3 | 0.97 | 2.44 | 2.8235 (15) | 103 |
O3—H3O···O1i | 0.82 | 1.82 | 2.6423 (12) | 174 |
C14—H14A···O1i | 0.97 | 2.53 | 3.1301 (17) | 120 |
N1—H1N···O2ii | 0.86 | 2.00 | 2.8591 (15) | 174 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2. |