Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009318/vj1106sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009318/vj1106Isup2.hkl |
CCDC reference: 152616
A mixture of cyclohexanone (0.1 mole), the appropriate aldehydes (0.2 mole) and absolute ethanol (75–100 ml) was added to a warm solution of ammonium acetate (0.15–0.20 mole) in absolute ethanol (200–250 ml). The mixture was gently warmed on a hot plate till the yellow colour turned orange. Dry ether (100 ml) was added to the reaction mixture after cooling and the solution was kept for 1 to 20 d, depending on the aldehyde used. Pale-yellow crystals of the ketone separated out and were washed with ethanol-ether and then recrystallized from benzene-petroleum ether [yield 80%, m.p. 490 K]. Query specific aldehyde, No. of days and temp range for pet ether.
All H atoms were located from difference Fourier maps and their displacement parameters were refined in four groups. Details? Geometrical calculations were performed using PARST (Nardelli, 1996).
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. H atoms are omitted for clarity. |
C22H25NO | F(000) = 688 |
Mr = 319.43 | Dx = 1.211 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.54180 Å |
a = 7.692 (3) Å | Cell parameters from 25 reflections |
b = 16.825 (3) Å | θ = 2–25° |
c = 13.7247 (18) Å | µ = 0.56 mm−1 |
β = 99.428 (18)° | T = 293 K |
V = 1752.1 (8) Å3 | Rectangular block, pale-yellow |
Z = 4 | 0.15 × 0.12 × 0.10 mm |
Rigaku AFC-7S diffractometer | 2380 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 70.1°, θmin = 3.3° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ-scan (North et al., 1968) | k = 0→20 |
Tmin = 0.928, Tmax = 0.942 | l = −16→16 |
3578 measured reflections | 3 standard reflections every 100 reflections |
3312 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.206 | Calculated w = 1/[σ2(Fo2) + (0.1042P)2 + 0.6146P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3312 reflections | Δρmax = 0.34 e Å−3 |
222 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0067 (10) |
C22H25NO | V = 1752.1 (8) Å3 |
Mr = 319.43 | Z = 4 |
Monoclinic, P21/a | Cu Kα radiation |
a = 7.692 (3) Å | µ = 0.56 mm−1 |
b = 16.825 (3) Å | T = 293 K |
c = 13.7247 (18) Å | 0.15 × 0.12 × 0.10 mm |
β = 99.428 (18)° |
Rigaku AFC-7S diffractometer | 2380 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (North et al., 1968) | Rint = 0.030 |
Tmin = 0.928, Tmax = 0.942 | 3 standard reflections every 100 reflections |
3578 measured reflections | intensity decay: none |
3312 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.206 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.34 e Å−3 |
3312 reflections | Δρmin = −0.43 e Å−3 |
222 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N3 | 0.1706 (2) | 0.53089 (12) | 0.67793 (14) | 0.0523 (5) | |
H3 | 0.0589 | 0.5288 | 0.6779 | 0.082 (2)* | |
O1 | 0.6712 (2) | 0.59560 (13) | 0.72250 (17) | 0.0768 (6) | |
C9 | 0.5137 (3) | 0.59620 (15) | 0.72622 (19) | 0.0564 (6) | |
C2 | 0.3010 (3) | 0.49294 (15) | 0.75338 (17) | 0.0523 (6) | |
H2 | 0.3680 | 0.4548 | 0.7202 | 0.082 (2)* | |
C5 | 0.3777 (3) | 0.63727 (15) | 0.65238 (18) | 0.0534 (6) | |
H5 | 0.4367 | 0.6619 | 0.6019 | 0.082 (2)* | |
C4 | 0.2498 (3) | 0.57258 (14) | 0.60271 (17) | 0.0503 (6) | |
H4 | 0.3183 | 0.5340 | 0.5711 | 0.082 (2)* | |
C1 | 0.4320 (3) | 0.55584 (16) | 0.80509 (19) | 0.0564 (6) | |
H1 | 0.5249 | 0.5285 | 0.8503 | 0.082 (2)* | |
C16 | 0.1110 (3) | 0.60799 (14) | 0.52393 (17) | 0.0504 (6) | |
C21 | 0.1460 (3) | 0.62139 (15) | 0.42837 (18) | 0.0544 (6) | |
C10 | 0.2125 (3) | 0.44759 (15) | 0.82667 (18) | 0.0532 (6) | |
C23 | 0.3139 (4) | 0.5945 (2) | 0.3952 (2) | 0.0734 (8) | |
H23A | 0.3274 | 0.5382 | 0.4049 | 0.129 (6)* | |
H23B | 0.4124 | 0.6214 | 0.4331 | 0.129 (6)* | |
H23C | 0.3088 | 0.6067 | 0.3264 | 0.129 (6)* | |
C20 | 0.0186 (4) | 0.65987 (16) | 0.36079 (19) | 0.0613 (7) | |
H20 | 0.0410 | 0.6691 | 0.2972 | 0.082 (2)* | |
C11 | 0.2944 (4) | 0.38124 (16) | 0.87707 (19) | 0.0593 (6) | |
C17 | −0.0509 (3) | 0.63142 (17) | 0.54732 (19) | 0.0595 (6) | |
H17 | −0.0768 | 0.6213 | 0.6100 | 0.082 (2)* | |
C15 | 0.0473 (3) | 0.47114 (17) | 0.8455 (2) | 0.0615 (7) | |
H15 | −0.0087 | 0.5144 | 0.8117 | 0.082 (2)* | |
C12 | 0.2083 (5) | 0.34299 (19) | 0.9449 (2) | 0.0756 (8) | |
H12 | 0.2621 | 0.2995 | 0.9791 | 0.082 (2)* | |
C19 | −0.1385 (4) | 0.68458 (17) | 0.3851 (2) | 0.0679 (7) | |
H19 | −0.2203 | 0.7111 | 0.3390 | 0.082 (2)* | |
C18 | −0.1739 (4) | 0.66980 (18) | 0.4779 (2) | 0.0697 (8) | |
H18 | −0.2811 | 0.6856 | 0.4945 | 0.082 (2)* | |
C14 | −0.0345 (4) | 0.4313 (2) | 0.9133 (2) | 0.0744 (8) | |
H14 | −0.1445 | 0.4480 | 0.9251 | 0.082 (2)* | |
C22 | 0.4696 (4) | 0.35003 (19) | 0.8588 (2) | 0.0759 (8) | |
H22A | 0.4648 | 0.3404 | 0.7895 | 0.129 (6)* | |
H22B | 0.4961 | 0.3013 | 0.8946 | 0.129 (6)* | |
H22C | 0.5598 | 0.3885 | 0.8807 | 0.129 (6)* | |
C13 | 0.0456 (5) | 0.3673 (2) | 0.9632 (2) | 0.0818 (9) | |
H13 | −0.0091 | 0.3405 | 1.0092 | 0.082 (2)* | |
C8 | 0.3509 (4) | 0.62076 (17) | 0.86298 (19) | 0.0638 (7) | |
H8A | 0.2893 | 0.5954 | 0.9109 | 0.082 (2)* | |
H8B | 0.4453 | 0.6525 | 0.8991 | 0.082 (2)* | |
C7 | 0.2235 (4) | 0.67548 (16) | 0.7987 (2) | 0.0629 (7) | |
H7A | 0.2007 | 0.7216 | 0.8372 | 0.082 (2)* | |
H7B | 0.1126 | 0.6479 | 0.7790 | 0.082 (2)* | |
C6 | 0.2925 (4) | 0.70325 (15) | 0.7066 (2) | 0.0592 (6) | |
H6A | 0.3788 | 0.7449 | 0.7251 | 0.082 (2)* | |
H6B | 0.1956 | 0.7262 | 0.6612 | 0.082 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N3 | 0.0457 (10) | 0.0580 (12) | 0.0532 (11) | −0.0026 (8) | 0.0085 (8) | 0.0034 (9) |
O1 | 0.0429 (10) | 0.0894 (15) | 0.1002 (16) | 0.0011 (9) | 0.0182 (9) | 0.0108 (12) |
C9 | 0.0488 (13) | 0.0553 (14) | 0.0655 (15) | −0.0024 (10) | 0.0106 (11) | −0.0039 (11) |
C2 | 0.0498 (12) | 0.0548 (13) | 0.0526 (13) | −0.0015 (10) | 0.0100 (10) | 0.0012 (10) |
C5 | 0.0488 (13) | 0.0557 (14) | 0.0569 (13) | −0.0062 (10) | 0.0126 (10) | 0.0034 (11) |
C4 | 0.0511 (13) | 0.0513 (13) | 0.0502 (12) | 0.0006 (10) | 0.0130 (10) | −0.0027 (10) |
C1 | 0.0463 (13) | 0.0626 (15) | 0.0586 (14) | −0.0044 (11) | 0.0034 (10) | 0.0044 (11) |
C16 | 0.0506 (13) | 0.0499 (12) | 0.0516 (12) | −0.0010 (10) | 0.0110 (10) | −0.0050 (10) |
C21 | 0.0602 (14) | 0.0521 (13) | 0.0517 (13) | −0.0054 (11) | 0.0119 (11) | −0.0070 (10) |
C10 | 0.0546 (13) | 0.0548 (13) | 0.0502 (12) | −0.0069 (10) | 0.0086 (10) | −0.0028 (10) |
C23 | 0.0703 (18) | 0.093 (2) | 0.0619 (16) | 0.0036 (15) | 0.0266 (14) | −0.0042 (15) |
C20 | 0.0755 (17) | 0.0573 (14) | 0.0490 (13) | −0.0064 (12) | 0.0034 (12) | −0.0014 (11) |
C11 | 0.0617 (15) | 0.0581 (14) | 0.0555 (14) | −0.0072 (11) | 0.0017 (11) | 0.0041 (11) |
C17 | 0.0517 (13) | 0.0695 (16) | 0.0578 (14) | 0.0023 (12) | 0.0111 (11) | −0.0053 (12) |
C15 | 0.0581 (15) | 0.0650 (15) | 0.0640 (15) | −0.0056 (12) | 0.0179 (12) | −0.0045 (12) |
C12 | 0.091 (2) | 0.0690 (18) | 0.0648 (16) | −0.0162 (16) | 0.0062 (15) | 0.0107 (14) |
C19 | 0.0682 (17) | 0.0638 (16) | 0.0655 (16) | 0.0047 (13) | −0.0073 (13) | −0.0034 (13) |
C18 | 0.0558 (15) | 0.0774 (18) | 0.0731 (18) | 0.0074 (13) | 0.0022 (13) | −0.0098 (15) |
C14 | 0.0740 (19) | 0.080 (2) | 0.0750 (19) | −0.0190 (15) | 0.0290 (15) | −0.0114 (16) |
C22 | 0.0687 (18) | 0.0756 (19) | 0.080 (2) | 0.0083 (15) | 0.0020 (15) | 0.0155 (16) |
C13 | 0.093 (2) | 0.086 (2) | 0.0718 (18) | −0.0297 (18) | 0.0297 (17) | 0.0039 (17) |
C8 | 0.0666 (16) | 0.0692 (17) | 0.0542 (14) | −0.0110 (13) | 0.0056 (12) | −0.0071 (12) |
C7 | 0.0651 (15) | 0.0608 (15) | 0.0644 (15) | −0.0010 (12) | 0.0148 (12) | −0.0134 (12) |
C6 | 0.0579 (14) | 0.0521 (13) | 0.0665 (15) | −0.0011 (11) | 0.0075 (12) | −0.0040 (12) |
N3—C4 | 1.461 (3) | C20—H20 | 0.9300 |
N3—C2 | 1.465 (3) | C11—C12 | 1.386 (4) |
N3—H3 | 0.8600 | C11—C22 | 1.506 (4) |
O1—C9 | 1.221 (3) | C17—C18 | 1.387 (4) |
C9—C1 | 1.500 (3) | C17—H17 | 0.9300 |
C9—C5 | 1.501 (3) | C15—C14 | 1.380 (4) |
C2—C10 | 1.511 (3) | C15—H15 | 0.9300 |
C2—C1 | 1.551 (3) | C12—C13 | 1.379 (5) |
C2—H2 | 0.9800 | C12—H12 | 0.9300 |
C5—C6 | 1.541 (3) | C19—C18 | 1.368 (4) |
C5—C4 | 1.548 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9800 | C18—H18 | 0.9300 |
C4—C16 | 1.512 (3) | C14—C13 | 1.367 (5) |
C4—H4 | 0.9800 | C14—H14 | 0.9300 |
C1—C8 | 1.542 (4) | C22—H22A | 0.9600 |
C1—H1 | 0.9800 | C22—H22B | 0.9600 |
C16—C17 | 1.393 (3) | C22—H22C | 0.9600 |
C16—C21 | 1.400 (3) | C13—H13 | 0.9300 |
C21—C20 | 1.393 (4) | C8—C7 | 1.517 (4) |
C21—C23 | 1.508 (4) | C8—H8A | 0.9700 |
C10—C15 | 1.395 (4) | C8—H8B | 0.9700 |
C10—C11 | 1.407 (4) | C7—C6 | 1.523 (4) |
C23—H23A | 0.9600 | C7—H7A | 0.9700 |
C23—H23B | 0.9600 | C7—H7B | 0.9700 |
C23—H23C | 0.9600 | C6—H6A | 0.9700 |
C20—C19 | 1.370 (4) | C6—H6B | 0.9700 |
C4—N3—C2 | 113.08 (18) | C12—C11—C10 | 118.3 (3) |
C4—N3—H3 | 123.5 | C12—C11—C22 | 119.3 (3) |
C2—N3—H3 | 123.5 | C10—C11—C22 | 122.4 (2) |
O1—C9—C1 | 124.2 (2) | C18—C17—C16 | 120.5 (3) |
O1—C9—C5 | 124.2 (2) | C18—C17—H17 | 119.7 |
C1—C9—C5 | 111.6 (2) | C16—C17—H17 | 119.7 |
N3—C2—C10 | 111.08 (19) | C14—C15—C10 | 121.1 (3) |
N3—C2—C1 | 110.1 (2) | C14—C15—H15 | 119.4 |
C10—C2—C1 | 111.72 (19) | C10—C15—H15 | 119.4 |
N3—C2—H2 | 107.9 | C13—C12—C11 | 122.2 (3) |
C10—C2—H2 | 107.9 | C13—C12—H12 | 118.9 |
C1—C2—H2 | 107.9 | C11—C12—H12 | 118.9 |
C9—C5—C6 | 108.1 (2) | C18—C19—C20 | 119.3 (3) |
C9—C5—C4 | 107.2 (2) | C18—C19—H19 | 120.3 |
C6—C5—C4 | 115.4 (2) | C20—C19—H19 | 120.3 |
C9—C5—H5 | 108.6 | C19—C18—C17 | 120.5 (3) |
C6—C5—H5 | 108.6 | C19—C18—H18 | 119.8 |
C4—C5—H5 | 108.6 | C17—C18—H18 | 119.8 |
N3—C4—C16 | 111.51 (19) | C13—C14—C15 | 120.2 (3) |
N3—C4—C5 | 109.55 (19) | C13—C14—H14 | 119.9 |
C16—C4—C5 | 111.17 (19) | C15—C14—H14 | 119.9 |
N3—C4—H4 | 108.2 | C11—C22—H22A | 109.5 |
C16—C4—H4 | 108.2 | C11—C22—H22B | 109.5 |
C5—C4—H4 | 108.2 | H22A—C22—H22B | 109.5 |
C9—C1—C8 | 107.7 (2) | C11—C22—H22C | 109.5 |
C9—C1—C2 | 107.2 (2) | H22A—C22—H22C | 109.5 |
C8—C1—C2 | 115.6 (2) | H22B—C22—H22C | 109.5 |
C9—C1—H1 | 108.7 | C14—C13—C12 | 119.4 (3) |
C8—C1—H1 | 108.7 | C14—C13—H13 | 120.3 |
C2—C1—H1 | 108.7 | C12—C13—H13 | 120.3 |
C17—C16—C21 | 119.1 (2) | C7—C8—C1 | 114.1 (2) |
C17—C16—C4 | 120.0 (2) | C7—C8—H8A | 108.7 |
C21—C16—C4 | 120.8 (2) | C1—C8—H8A | 108.7 |
C20—C21—C16 | 118.5 (2) | C7—C8—H8B | 108.7 |
C20—C21—C23 | 118.8 (2) | C1—C8—H8B | 108.7 |
C16—C21—C23 | 122.7 (2) | H8A—C8—H8B | 107.6 |
C15—C10—C11 | 118.9 (2) | C8—C7—C6 | 112.9 (2) |
C15—C10—C2 | 120.2 (2) | C8—C7—H7A | 109.0 |
C11—C10—C2 | 120.9 (2) | C6—C7—H7A | 109.0 |
C21—C23—H23A | 109.5 | C8—C7—H7B | 109.0 |
C21—C23—H23B | 109.5 | C6—C7—H7B | 109.0 |
H23A—C23—H23B | 109.5 | H7A—C7—H7B | 107.8 |
C21—C23—H23C | 109.5 | C7—C6—C5 | 114.4 (2) |
H23A—C23—H23C | 109.5 | C7—C6—H6A | 108.7 |
H23B—C23—H23C | 109.5 | C5—C6—H6A | 108.7 |
C19—C20—C21 | 122.1 (3) | C7—C6—H6B | 108.7 |
C19—C20—H20 | 119.0 | C5—C6—H6B | 108.7 |
C21—C20—H20 | 119.0 | H6A—C6—H6B | 107.6 |
C4—N3—C2—C10 | −177.41 (19) | N3—C2—C10—C15 | −27.8 (3) |
C4—N3—C2—C1 | 58.3 (2) | C1—C2—C10—C15 | 95.6 (3) |
O1—C9—C5—C6 | −116.8 (3) | N3—C2—C10—C11 | 152.2 (2) |
C1—C9—C5—C6 | 63.3 (3) | C1—C2—C10—C11 | −84.3 (3) |
O1—C9—C5—C4 | 118.1 (3) | C16—C21—C20—C19 | −0.1 (4) |
C1—C9—C5—C4 | −61.8 (3) | C23—C21—C20—C19 | 178.7 (3) |
C2—N3—C4—C16 | 177.62 (19) | C15—C10—C11—C12 | −1.2 (4) |
C2—N3—C4—C5 | −58.9 (3) | C2—C10—C11—C12 | 178.7 (2) |
C9—C5—C4—N3 | 58.4 (2) | C15—C10—C11—C22 | 177.9 (3) |
C6—C5—C4—N3 | −62.1 (3) | C2—C10—C11—C22 | −2.2 (4) |
C9—C5—C4—C16 | −177.90 (19) | C21—C16—C17—C18 | −2.0 (4) |
C6—C5—C4—C16 | 61.6 (3) | C4—C16—C17—C18 | 174.8 (2) |
O1—C9—C1—C8 | 116.0 (3) | C11—C10—C15—C14 | 1.0 (4) |
C5—C9—C1—C8 | −64.1 (3) | C2—C10—C15—C14 | −178.9 (2) |
O1—C9—C1—C2 | −119.0 (3) | C10—C11—C12—C13 | 0.8 (4) |
C5—C9—C1—C2 | 60.8 (3) | C22—C11—C12—C13 | −178.4 (3) |
N3—C2—C1—C9 | −56.9 (2) | C21—C20—C19—C18 | −1.3 (4) |
C10—C2—C1—C9 | 179.2 (2) | C20—C19—C18—C17 | 1.1 (4) |
N3—C2—C1—C8 | 63.2 (3) | C16—C17—C18—C19 | 0.6 (4) |
C10—C2—C1—C8 | −60.7 (3) | C10—C15—C14—C13 | −0.3 (4) |
N3—C4—C16—C17 | 29.3 (3) | C15—C14—C13—C12 | −0.2 (5) |
C5—C4—C16—C17 | −93.3 (3) | C11—C12—C13—C14 | 0.0 (5) |
N3—C4—C16—C21 | −154.0 (2) | C9—C1—C8—C7 | 54.0 (3) |
C5—C4—C16—C21 | 83.5 (3) | C2—C1—C8—C7 | −65.8 (3) |
C17—C16—C21—C20 | 1.8 (4) | C1—C8—C7—C6 | −45.0 (3) |
C4—C16—C21—C20 | −175.0 (2) | C8—C7—C6—C5 | 44.1 (3) |
C17—C16—C21—C23 | −177.0 (2) | C9—C5—C6—C7 | −52.1 (3) |
C4—C16—C21—C23 | 6.3 (4) | C4—C5—C6—C7 | 67.9 (3) |
Experimental details
Crystal data | |
Chemical formula | C22H25NO |
Mr | 319.43 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 293 |
a, b, c (Å) | 7.692 (3), 16.825 (3), 13.7247 (18) |
β (°) | 99.428 (18) |
V (Å3) | 1752.1 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | ψ-scan (North et al., 1968) |
Tmin, Tmax | 0.928, 0.942 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3578, 3312, 2380 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.206, 1.10 |
No. of reflections | 3312 |
No. of parameters | 222 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.43 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97.
N3—C4 | 1.461 (3) | O1—C9 | 1.221 (3) |
N3—C2 | 1.465 (3) | ||
C4—N3—C2 | 113.08 (18) | N3—C2—C1 | 110.1 (2) |
O1—C9—C5 | 124.2 (2) | N3—C4—C16 | 111.51 (19) |
N3—C2—C10 | 111.08 (19) | N3—C4—C5 | 109.55 (19) |
C4—N3—C2—C1 | 58.3 (2) | N3—C2—C1—C9 | −56.9 (2) |
C1—C9—C5—C6 | 63.3 (3) | C10—C2—C1—C8 | −60.7 (3) |
C1—C9—C5—C4 | −61.8 (3) | C9—C1—C8—C7 | 54.0 (3) |
C2—N3—C4—C5 | −58.9 (3) | C2—C1—C8—C7 | −65.8 (3) |
C9—C5—C4—N3 | 58.4 (2) | C1—C8—C7—C6 | −45.0 (3) |
C9—C5—C4—C16 | −177.90 (19) | C8—C7—C6—C5 | 44.1 (3) |
C6—C5—C4—C16 | 61.6 (3) | C9—C5—C6—C7 | −52.1 (3) |
C5—C9—C1—C8 | −64.1 (3) | C4—C5—C6—C7 | 67.9 (3) |
C5—C9—C1—C2 | 60.8 (3) |
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The bicyclic nonane ring can exist in chair-chair, chair-boat and boat-boat conformations. Among these, the chair-chair conformation is the most favourable. In the present study of the title compound, (I), the bicyclic ring system also adopts the chair-chair conformation. \sch
In the cyclohexane ring of (I), atoms C7 and C9 deviate from the C8/C1/C5/C6 plane by −0.537 (4) and 0.720 (3) Å, respectively, indicating a departure from the ideal chair conformation (Brown et al., 1965; Webb & Becker, 1967). The piperidine ring has near-ideal chair conformation. The phenyl rings are equatorially disposed with respect to the piperidine ring, with the torsion angles C9—C5—C4—C16 − 177.9 (2) and C10—C2—C1—C9 179.2 (2)°. They are oriented at an angle of 29.4 (1)° to each other. The orientations of the two o-tolyl groups are such that their methyl groups point towards the carbonyl group in the fused ring system.