Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008985/ob6240sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008985/ob6240Isup2.hkl |
CCDC reference: 214637
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.063
- wR factor = 0.181
- Data-to-parameter ratio = 13.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A mixture of 1-benzyl-3,5-dibenzylidene-piperidin-4-one (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) were refluxed in methanol (80 ml) until the disapperence of the starting material as evidenced by the thin-layer chromatography. After the reaction was complete, the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound, (I). 20 mg of (I) was dissolved in 15 ml chloroform, the solution was kept at room temperature for 15 d by natural evaporation to give colorless single crystals of (I), suitable for X-ray analysis. M.p. 487–488 K; IR (KBr, cm−1): 3493 (N—H), 1694, 1682 (C═O); 1H NMR (CDCl3, p.p.m.): 1.86 (1H, d), 2.16 (3H, s), 2.76–2.81 (1H, m), 3.18 (1H, d), 3.41 (2H, m), 3.42–3.64 (1H, m), 3.93 (1H, d), 3.94–4.00 (1H, m), 4.80–4.86 (1H, m), 6.67 (1H, s), 6.67–7.37 (19H, m); 7.40 (1H, br).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. | |
Fig. 2. The crystal structure of (I), viewed along a axis. The broken lines indicate hydrogen bonds. |
C36H33N3O2 | Z = 2 |
Mr = 539.65 | F(000) = 572 |
Triclinic, P1 | Dx = 1.222 Mg m−3 |
a = 8.535 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.441 (4) Å | Cell parameters from 715 reflections |
c = 15.682 (6) Å | θ = 2.5–25.5° |
α = 102.027 (7)° | µ = 0.08 mm−1 |
β = 92.423 (7)° | T = 293 K |
γ = 100.637 (7)° | Plate, colorless |
V = 1466.8 (10) Å3 | 0.22 × 0.16 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 2883 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 1.3° |
ϕ and ω scans | h = −10→10 |
7663 measured reflections | k = −13→8 |
5152 independent reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.084P)2P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.181 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.30 e Å−3 |
5152 reflections | Δρmin = −0.25 e Å−3 |
372 parameters |
C36H33N3O2 | γ = 100.637 (7)° |
Mr = 539.65 | V = 1466.8 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.535 (3) Å | Mo Kα radiation |
b = 11.441 (4) Å | µ = 0.08 mm−1 |
c = 15.682 (6) Å | T = 293 K |
α = 102.027 (7)° | 0.22 × 0.16 × 0.08 mm |
β = 92.423 (7)° |
Bruker SMART CCD area-detector diffractometer | 2883 reflections with I > 2σ(I) |
7663 measured reflections | Rint = 0.030 |
5152 independent reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.30 e Å−3 |
5152 reflections | Δρmin = −0.25 e Å−3 |
372 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 | ||
N1 | 0.3290 (3) | 0.5441 (2) | 0.19416 (15) | 0.0464 (7) | |
N2 | −0.0016 (3) | 0.7926 (3) | 0.22094 (17) | 0.0584 (8) | |
N3 | −0.0354 (3) | 0.4988 (2) | 0.10941 (15) | 0.0521 (7) | |
H3A | −0.0542 | 0.4452 | 0.0609 | 0.062* | |
O1 | 0.1237 (3) | 0.6503 (2) | 0.06047 (13) | 0.0611 (7) | |
O2 | 0.2191 (3) | 0.7492 (2) | 0.41867 (13) | 0.0623 (7) | |
C1 | 0.3621 (4) | 0.6767 (3) | 0.20849 (19) | 0.0472 (8) | |
H1A | 0.3601 | 0.7006 | 0.1527 | 0.057* | |
H1B | 0.4677 | 0.7095 | 0.2386 | 0.057* | |
C2 | 0.3736 (4) | 0.5101 (3) | 0.27590 (19) | 0.0518 (8) | |
H2A | 0.4866 | 0.5417 | 0.2929 | 0.062* | |
H2B | 0.3546 | 0.4220 | 0.2671 | 0.062* | |
C3 | 0.2772 (4) | 0.5607 (3) | 0.34652 (18) | 0.0455 (8) | |
C4 | 0.2428 (3) | 0.6845 (3) | 0.35056 (19) | 0.0469 (8) | |
C5 | 0.2364 (4) | 0.7276 (3) | 0.26335 (18) | 0.0447 (8) | |
C6 | 0.2577 (4) | 0.8684 (3) | 0.2798 (2) | 0.0524 (9) | |
H6 | 0.2227 | 0.8954 | 0.3381 | 0.063* | |
C7 | 0.1325 (4) | 0.8871 (3) | 0.2147 (2) | 0.0655 (10) | |
H7A | 0.1068 | 0.9675 | 0.2314 | 0.079* | |
H7B | 0.1676 | 0.8759 | 0.1560 | 0.079* | |
C8 | 0.0597 (4) | 0.6802 (3) | 0.21619 (18) | 0.0481 (8) | |
C9 | 0.0591 (4) | 0.6091 (3) | 0.11943 (19) | 0.0485 (8) | |
C10 | −0.1000 (4) | 0.4817 (3) | 0.18775 (18) | 0.0468 (8) | |
C11 | −0.0524 (4) | 0.5884 (3) | 0.25167 (18) | 0.0469 (8) | |
C12 | −0.1153 (4) | 0.5948 (4) | 0.33169 (19) | 0.0569 (9) | |
H12 | −0.0910 | 0.6668 | 0.3743 | 0.068* | |
C13 | −0.2137 (4) | 0.4943 (4) | 0.3479 (2) | 0.0634 (10) | |
H13 | −0.2550 | 0.4986 | 0.4022 | 0.076* | |
C14 | −0.2526 (4) | 0.3871 (4) | 0.2856 (2) | 0.0634 (10) | |
H14 | −0.3155 | 0.3189 | 0.2990 | 0.076* | |
C15 | −0.1985 (4) | 0.3802 (3) | 0.2029 (2) | 0.0583 (9) | |
H15 | −0.2278 | 0.3094 | 0.1593 | 0.070* | |
C16 | 0.4123 (4) | 0.4874 (3) | 0.1216 (2) | 0.0606 (10) | |
H16A | 0.5262 | 0.5062 | 0.1389 | 0.073* | |
H16B | 0.3956 | 0.5233 | 0.0719 | 0.073* | |
C17 | 0.3591 (5) | 0.3507 (3) | 0.0931 (2) | 0.0588 (9) | |
C18 | 0.4556 (5) | 0.2844 (4) | 0.0435 (2) | 0.0753 (12) | |
H18 | 0.5537 | 0.3239 | 0.0300 | 0.090* | |
C19 | 0.4078 (7) | 0.1594 (4) | 0.0135 (3) | 0.0939 (15) | |
H19 | 0.4738 | 0.1157 | −0.0202 | 0.113* | |
C20 | 0.2637 (9) | 0.0996 (5) | 0.0332 (3) | 0.1075 (18) | |
H20 | 0.2318 | 0.0158 | 0.0129 | 0.129* | |
C21 | 0.1685 (7) | 0.1637 (4) | 0.0823 (3) | 0.0947 (15) | |
H21 | 0.0715 | 0.1233 | 0.0963 | 0.114* | |
C22 | 0.2140 (5) | 0.2892 (4) | 0.1120 (3) | 0.0740 (11) | |
H22 | 0.1464 | 0.3322 | 0.1449 | 0.089* | |
C23 | 0.2149 (4) | 0.5008 (3) | 0.40564 (19) | 0.0517 (9) | |
H23 | 0.1514 | 0.5403 | 0.4441 | 0.062* | |
C24 | 0.2343 (4) | 0.3802 (3) | 0.41726 (19) | 0.0505 (9) | |
C25 | 0.3816 (5) | 0.3487 (4) | 0.4197 (2) | 0.0659 (10) | |
H25 | 0.4706 | 0.4034 | 0.4101 | 0.079* | |
C26 | 0.4014 (5) | 0.2397 (4) | 0.4358 (3) | 0.0808 (12) | |
H26 | 0.5031 | 0.2214 | 0.4375 | 0.097* | |
C27 | 0.2733 (6) | 0.1573 (4) | 0.4496 (3) | 0.0809 (12) | |
H27 | 0.2867 | 0.0822 | 0.4594 | 0.097* | |
C28 | 0.1244 (6) | 0.1863 (4) | 0.4490 (3) | 0.0809 (13) | |
H28 | 0.0365 | 0.1309 | 0.4590 | 0.097* | |
C29 | 0.1045 (5) | 0.2974 (4) | 0.4335 (2) | 0.0699 (11) | |
H29 | 0.0034 | 0.3168 | 0.4340 | 0.084* | |
C30 | 0.4274 (4) | 0.9372 (3) | 0.2810 (2) | 0.0567 (9) | |
C31 | 0.5353 (5) | 0.9460 (4) | 0.3505 (3) | 0.0837 (13) | |
H31 | 0.5032 | 0.9086 | 0.3959 | 0.100* | |
C32 | 0.6903 (5) | 1.0092 (4) | 0.3544 (3) | 0.0987 (15) | |
H32 | 0.7618 | 1.0129 | 0.4017 | 0.118* | |
C33 | 0.7394 (5) | 1.0662 (4) | 0.2892 (3) | 0.0891 (14) | |
H33 | 0.8434 | 1.1099 | 0.2920 | 0.107* | |
C34 | 0.6337 (6) | 1.0579 (4) | 0.2206 (3) | 0.0923 (15) | |
H34 | 0.6661 | 1.0955 | 0.1753 | 0.111* | |
C35 | 0.4790 (5) | 0.9948 (3) | 0.2166 (2) | 0.0744 (12) | |
H35 | 0.4082 | 0.9914 | 0.1690 | 0.089* | |
C36 | −0.1439 (5) | 0.7821 (4) | 0.1619 (3) | 0.0804 (12) | |
H36A | −0.1814 | 0.8575 | 0.1735 | 0.121* | |
H36B | −0.2264 | 0.7176 | 0.1711 | 0.121* | |
H36C | −0.1172 | 0.7642 | 0.1023 | 0.121* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0580 (16) | 0.0462 (16) | 0.0383 (14) | 0.0167 (14) | 0.0087 (12) | 0.0098 (12) |
N2 | 0.0595 (18) | 0.0513 (18) | 0.0610 (17) | 0.0175 (16) | −0.0123 (14) | 0.0024 (14) |
N3 | 0.0659 (18) | 0.0519 (18) | 0.0319 (14) | 0.0055 (15) | 0.0017 (12) | 0.0010 (12) |
O1 | 0.0765 (16) | 0.0631 (15) | 0.0368 (12) | −0.0011 (13) | −0.0012 (11) | 0.0101 (11) |
O2 | 0.0771 (16) | 0.0704 (16) | 0.0369 (12) | 0.0244 (14) | 0.0015 (11) | −0.0019 (11) |
C1 | 0.0524 (19) | 0.049 (2) | 0.0395 (16) | 0.0098 (17) | 0.0026 (14) | 0.0089 (14) |
C2 | 0.056 (2) | 0.059 (2) | 0.0472 (18) | 0.0217 (18) | 0.0098 (15) | 0.0163 (16) |
C3 | 0.0463 (18) | 0.054 (2) | 0.0364 (16) | 0.0154 (16) | −0.0010 (14) | 0.0078 (15) |
C4 | 0.0426 (18) | 0.058 (2) | 0.0374 (17) | 0.0119 (17) | −0.0011 (14) | 0.0029 (16) |
C5 | 0.0510 (19) | 0.0461 (19) | 0.0358 (16) | 0.0117 (16) | −0.0013 (14) | 0.0052 (14) |
C6 | 0.065 (2) | 0.045 (2) | 0.0421 (17) | 0.0117 (18) | −0.0049 (15) | 0.0001 (15) |
C7 | 0.083 (3) | 0.048 (2) | 0.065 (2) | 0.021 (2) | −0.0129 (19) | 0.0061 (17) |
C8 | 0.057 (2) | 0.0458 (19) | 0.0371 (16) | 0.0109 (17) | −0.0064 (14) | 0.0004 (14) |
C9 | 0.054 (2) | 0.052 (2) | 0.0361 (17) | 0.0082 (18) | −0.0031 (15) | 0.0055 (15) |
C10 | 0.0498 (19) | 0.053 (2) | 0.0377 (16) | 0.0130 (17) | −0.0002 (14) | 0.0097 (15) |
C11 | 0.0449 (18) | 0.058 (2) | 0.0366 (16) | 0.0154 (16) | −0.0011 (14) | 0.0032 (15) |
C12 | 0.0481 (19) | 0.080 (3) | 0.0396 (18) | 0.019 (2) | 0.0003 (15) | 0.0008 (17) |
C13 | 0.047 (2) | 0.099 (3) | 0.047 (2) | 0.016 (2) | 0.0077 (16) | 0.020 (2) |
C14 | 0.056 (2) | 0.077 (3) | 0.061 (2) | 0.011 (2) | 0.0089 (18) | 0.024 (2) |
C15 | 0.061 (2) | 0.053 (2) | 0.059 (2) | 0.0101 (19) | 0.0026 (17) | 0.0087 (17) |
C16 | 0.074 (2) | 0.059 (2) | 0.053 (2) | 0.020 (2) | 0.0185 (18) | 0.0120 (17) |
C17 | 0.084 (3) | 0.058 (2) | 0.0394 (18) | 0.027 (2) | 0.0015 (17) | 0.0109 (16) |
C18 | 0.112 (3) | 0.077 (3) | 0.046 (2) | 0.049 (3) | 0.004 (2) | 0.008 (2) |
C19 | 0.151 (5) | 0.077 (3) | 0.061 (3) | 0.065 (3) | −0.003 (3) | −0.003 (2) |
C20 | 0.167 (6) | 0.063 (3) | 0.091 (4) | 0.039 (4) | −0.029 (4) | 0.007 (3) |
C21 | 0.119 (4) | 0.060 (3) | 0.101 (4) | 0.010 (3) | −0.020 (3) | 0.020 (3) |
C22 | 0.089 (3) | 0.058 (3) | 0.076 (3) | 0.019 (2) | 0.002 (2) | 0.015 (2) |
C23 | 0.054 (2) | 0.064 (2) | 0.0394 (17) | 0.0189 (18) | 0.0056 (15) | 0.0097 (16) |
C24 | 0.055 (2) | 0.059 (2) | 0.0394 (17) | 0.0129 (19) | 0.0093 (15) | 0.0118 (15) |
C25 | 0.065 (2) | 0.072 (3) | 0.072 (2) | 0.019 (2) | 0.0164 (19) | 0.033 (2) |
C26 | 0.083 (3) | 0.087 (3) | 0.090 (3) | 0.036 (3) | 0.019 (2) | 0.040 (3) |
C27 | 0.111 (4) | 0.064 (3) | 0.071 (3) | 0.020 (3) | 0.004 (2) | 0.019 (2) |
C28 | 0.089 (3) | 0.066 (3) | 0.079 (3) | −0.013 (3) | 0.002 (2) | 0.020 (2) |
C29 | 0.061 (2) | 0.079 (3) | 0.065 (2) | 0.003 (2) | −0.0015 (18) | 0.018 (2) |
C30 | 0.073 (2) | 0.0384 (19) | 0.053 (2) | 0.0081 (18) | −0.0017 (18) | 0.0008 (16) |
C31 | 0.072 (3) | 0.092 (3) | 0.077 (3) | −0.013 (3) | −0.021 (2) | 0.027 (2) |
C32 | 0.078 (3) | 0.103 (4) | 0.106 (4) | −0.006 (3) | −0.022 (3) | 0.029 (3) |
C33 | 0.078 (3) | 0.066 (3) | 0.107 (4) | −0.012 (2) | −0.001 (3) | 0.007 (3) |
C34 | 0.114 (4) | 0.069 (3) | 0.082 (3) | −0.011 (3) | 0.009 (3) | 0.017 (2) |
C35 | 0.092 (3) | 0.056 (2) | 0.064 (2) | −0.004 (2) | −0.008 (2) | 0.009 (2) |
C36 | 0.072 (3) | 0.079 (3) | 0.090 (3) | 0.029 (2) | −0.021 (2) | 0.010 (2) |
N1—C1 | 1.458 (4) | C16—H16A | 0.9700 |
N1—C16 | 1.468 (4) | C16—H16B | 0.9700 |
N1—C2 | 1.470 (4) | C17—C18 | 1.377 (5) |
N2—C7 | 1.445 (4) | C17—C22 | 1.383 (5) |
N2—C8 | 1.465 (4) | C18—C19 | 1.387 (6) |
N2—C36 | 1.467 (4) | C18—H18 | 0.9300 |
N3—C9 | 1.341 (4) | C19—C20 | 1.373 (7) |
N3—C10 | 1.403 (4) | C19—H19 | 0.9300 |
N3—H3A | 0.8600 | C20—C21 | 1.352 (7) |
O1—C9 | 1.229 (3) | C20—H20 | 0.9300 |
O2—C4 | 1.214 (3) | C21—C22 | 1.389 (6) |
C1—C5 | 1.527 (4) | C21—H21 | 0.9300 |
C1—H1A | 0.9700 | C22—H22 | 0.9300 |
C1—H1B | 0.9700 | C23—C24 | 1.467 (5) |
C2—C3 | 1.491 (4) | C23—H23 | 0.9300 |
C2—H2A | 0.9700 | C24—C25 | 1.372 (5) |
C2—H2B | 0.9700 | C24—C29 | 1.389 (4) |
C3—C23 | 1.336 (4) | C25—C26 | 1.361 (5) |
C3—C4 | 1.488 (4) | C25—H25 | 0.9300 |
C4—C5 | 1.550 (4) | C26—C27 | 1.362 (5) |
C5—C6 | 1.553 (4) | C26—H26 | 0.9300 |
C5—C8 | 1.597 (4) | C27—C28 | 1.371 (6) |
C6—C30 | 1.513 (5) | C27—H27 | 0.9300 |
C6—C7 | 1.521 (5) | C28—C29 | 1.381 (6) |
C6—H6 | 0.9800 | C28—H28 | 0.9300 |
C7—H7A | 0.9700 | C29—H29 | 0.9300 |
C7—H7B | 0.9700 | C30—C35 | 1.361 (5) |
C8—C11 | 1.499 (4) | C30—C31 | 1.372 (5) |
C8—C9 | 1.564 (4) | C31—C32 | 1.377 (5) |
C10—C15 | 1.372 (4) | C31—H31 | 0.9300 |
C10—C11 | 1.390 (4) | C32—C33 | 1.364 (6) |
C11—C12 | 1.379 (4) | C32—H32 | 0.9300 |
C12—C13 | 1.369 (5) | C33—C34 | 1.351 (6) |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.375 (5) | C34—C35 | 1.375 (5) |
C13—H13 | 0.9300 | C34—H34 | 0.9300 |
C14—C15 | 1.388 (5) | C35—H35 | 0.9300 |
C14—H14 | 0.9300 | C36—H36A | 0.9600 |
C15—H15 | 0.9300 | C36—H36B | 0.9600 |
C16—C17 | 1.510 (5) | C36—H36C | 0.9600 |
C1—N1—C16 | 112.1 (2) | C14—C15—H15 | 121.3 |
C1—N1—C2 | 108.7 (2) | N1—C16—C17 | 114.3 (3) |
C16—N1—C2 | 111.1 (3) | N1—C16—H16A | 108.7 |
C7—N2—C8 | 107.0 (3) | C17—C16—H16A | 108.7 |
C7—N2—C36 | 115.6 (3) | N1—C16—H16B | 108.7 |
C8—N2—C36 | 115.4 (3) | C17—C16—H16B | 108.7 |
C9—N3—C10 | 111.7 (3) | H16A—C16—H16B | 107.6 |
C9—N3—H3A | 124.1 | C18—C17—C22 | 118.2 (4) |
C10—N3—H3A | 124.1 | C18—C17—C16 | 119.1 (4) |
N1—C1—C5 | 109.5 (2) | C22—C17—C16 | 122.7 (3) |
N1—C1—H1A | 109.8 | C17—C18—C19 | 120.6 (4) |
C5—C1—H1A | 109.8 | C17—C18—H18 | 119.7 |
N1—C1—H1B | 109.8 | C19—C18—H18 | 119.7 |
C5—C1—H1B | 109.8 | C20—C19—C18 | 120.4 (5) |
H1A—C1—H1B | 108.2 | C20—C19—H19 | 119.8 |
N1—C2—C3 | 109.8 (3) | C18—C19—H19 | 119.8 |
N1—C2—H2A | 109.7 | C21—C20—C19 | 119.5 (5) |
C3—C2—H2A | 109.7 | C21—C20—H20 | 120.3 |
N1—C2—H2B | 109.7 | C19—C20—H20 | 120.3 |
C3—C2—H2B | 109.7 | C20—C21—C22 | 120.8 (5) |
H2A—C2—H2B | 108.2 | C20—C21—H21 | 119.6 |
C23—C3—C4 | 117.1 (3) | C22—C21—H21 | 119.6 |
C23—C3—C2 | 124.3 (3) | C17—C22—C21 | 120.5 (5) |
C4—C3—C2 | 118.6 (3) | C17—C22—H22 | 119.8 |
O2—C4—C3 | 122.0 (3) | C21—C22—H22 | 119.8 |
O2—C4—C5 | 120.9 (3) | C3—C23—C24 | 127.8 (3) |
C3—C4—C5 | 117.1 (3) | C3—C23—H23 | 116.1 |
C1—C5—C4 | 107.5 (3) | C24—C23—H23 | 116.1 |
C1—C5—C6 | 113.6 (3) | C25—C24—C29 | 117.5 (3) |
C4—C5—C6 | 111.3 (2) | C25—C24—C23 | 121.8 (3) |
C1—C5—C8 | 112.4 (2) | C29—C24—C23 | 120.5 (3) |
C4—C5—C8 | 108.6 (2) | C26—C25—C24 | 122.0 (4) |
C6—C5—C8 | 103.3 (3) | C26—C25—H25 | 119.0 |
C30—C6—C7 | 117.7 (3) | C24—C25—H25 | 119.0 |
C30—C6—C5 | 115.6 (3) | C25—C26—C27 | 120.4 (4) |
C7—C6—C5 | 103.4 (2) | C25—C26—H26 | 119.8 |
C30—C6—H6 | 106.4 | C27—C26—H26 | 119.8 |
C7—C6—H6 | 106.4 | C26—C27—C28 | 119.4 (4) |
C5—C6—H6 | 106.4 | C26—C27—H27 | 120.3 |
N2—C7—C6 | 101.7 (3) | C28—C27—H27 | 120.3 |
N2—C7—H7A | 111.4 | C27—C28—C29 | 120.2 (4) |
C6—C7—H7A | 111.4 | C27—C28—H28 | 119.9 |
N2—C7—H7B | 111.4 | C29—C28—H28 | 119.9 |
C6—C7—H7B | 111.4 | C28—C29—C24 | 120.5 (4) |
H7A—C7—H7B | 109.3 | C28—C29—H29 | 119.8 |
N2—C8—C11 | 111.4 (3) | C24—C29—H29 | 119.8 |
N2—C8—C9 | 111.7 (3) | C35—C30—C31 | 117.3 (3) |
C11—C8—C9 | 100.5 (2) | C35—C30—C6 | 123.0 (3) |
N2—C8—C5 | 103.3 (2) | C31—C30—C6 | 119.6 (3) |
C11—C8—C5 | 117.9 (2) | C30—C31—C32 | 121.3 (4) |
C9—C8—C5 | 112.4 (2) | C30—C31—H31 | 119.4 |
O1—C9—N3 | 125.2 (3) | C32—C31—H31 | 119.4 |
O1—C9—C8 | 125.9 (3) | C33—C32—C31 | 120.4 (4) |
N3—C9—C8 | 108.6 (3) | C33—C32—H32 | 119.8 |
C15—C10—C11 | 122.7 (3) | C31—C32—H32 | 119.8 |
C15—C10—N3 | 128.1 (3) | C34—C33—C32 | 118.6 (4) |
C11—C10—N3 | 109.1 (3) | C34—C33—H33 | 120.7 |
C12—C11—C10 | 118.4 (3) | C32—C33—H33 | 120.7 |
C12—C11—C8 | 131.6 (3) | C33—C34—C35 | 121.0 (4) |
C10—C11—C8 | 109.9 (3) | C33—C34—H34 | 119.5 |
C13—C12—C11 | 119.5 (3) | C35—C34—H34 | 119.5 |
C13—C12—H12 | 120.2 | C30—C35—C34 | 121.4 (4) |
C11—C12—H12 | 120.2 | C30—C35—H35 | 119.3 |
C12—C13—C14 | 121.3 (3) | C34—C35—H35 | 119.3 |
C12—C13—H13 | 119.3 | N2—C36—H36A | 109.5 |
C14—C13—H13 | 119.3 | N2—C36—H36B | 109.5 |
C13—C14—C15 | 120.4 (3) | H36A—C36—H36B | 109.5 |
C13—C14—H14 | 119.8 | N2—C36—H36C | 109.5 |
C15—C14—H14 | 119.8 | H36A—C36—H36C | 109.5 |
C10—C15—C14 | 117.4 (3) | H36B—C36—H36C | 109.5 |
C10—C15—H15 | 121.3 | ||
C16—N1—C1—C5 | 162.6 (2) | C15—C10—C11—C12 | −4.3 (5) |
C2—N1—C1—C5 | −74.1 (3) | N3—C10—C11—C12 | 174.0 (3) |
C1—N1—C2—C3 | 60.7 (3) | C15—C10—C11—C8 | 177.7 (3) |
C16—N1—C2—C3 | −175.4 (3) | N3—C10—C11—C8 | −4.0 (4) |
N1—C2—C3—C23 | 139.4 (3) | N2—C8—C11—C12 | −56.1 (4) |
N1—C2—C3—C4 | −38.5 (4) | C9—C8—C11—C12 | −174.6 (3) |
C23—C3—C4—O2 | 29.0 (4) | C5—C8—C11—C12 | 63.0 (5) |
C2—C3—C4—O2 | −152.9 (3) | N2—C8—C11—C10 | 121.6 (3) |
C23—C3—C4—C5 | −150.3 (3) | C9—C8—C11—C10 | 3.1 (3) |
C2—C3—C4—C5 | 27.8 (4) | C5—C8—C11—C10 | −119.3 (3) |
N1—C1—C5—C4 | 58.3 (3) | C10—C11—C12—C13 | 4.2 (5) |
N1—C1—C5—C6 | −178.1 (2) | C8—C11—C12—C13 | −178.3 (3) |
N1—C1—C5—C8 | −61.2 (3) | C11—C12—C13—C14 | −0.7 (5) |
O2—C4—C5—C1 | 145.1 (3) | C12—C13—C14—C15 | −3.0 (6) |
C3—C4—C5—C1 | −35.6 (3) | C11—C10—C15—C14 | 0.7 (5) |
O2—C4—C5—C6 | 20.0 (4) | N3—C10—C15—C14 | −177.3 (3) |
C3—C4—C5—C6 | −160.6 (3) | C13—C14—C15—C10 | 2.9 (5) |
O2—C4—C5—C8 | −93.1 (3) | C1—N1—C16—C17 | −169.3 (3) |
C3—C4—C5—C8 | 86.2 (3) | C2—N1—C16—C17 | 68.8 (4) |
C1—C5—C6—C30 | −28.7 (4) | N1—C16—C17—C18 | −162.4 (3) |
C4—C5—C6—C30 | 92.8 (3) | N1—C16—C17—C22 | 20.0 (5) |
C8—C5—C6—C30 | −150.7 (3) | C22—C17—C18—C19 | 0.1 (5) |
C1—C5—C6—C7 | 101.5 (3) | C16—C17—C18—C19 | −177.6 (3) |
C4—C5—C6—C7 | −137.0 (3) | C17—C18—C19—C20 | −0.3 (6) |
C8—C5—C6—C7 | −20.6 (3) | C18—C19—C20—C21 | −0.1 (7) |
C8—N2—C7—C6 | −47.3 (3) | C19—C20—C21—C22 | 0.8 (7) |
C36—N2—C7—C6 | −177.4 (3) | C18—C17—C22—C21 | 0.6 (5) |
C30—C6—C7—N2 | 169.7 (3) | C16—C17—C22—C21 | 178.2 (3) |
C5—C6—C7—N2 | 40.8 (3) | C20—C21—C22—C17 | −1.1 (7) |
C7—N2—C8—C11 | 160.8 (2) | C4—C3—C23—C24 | −178.1 (3) |
C36—N2—C8—C11 | −69.0 (4) | C2—C3—C23—C24 | 3.9 (5) |
C7—N2—C8—C9 | −87.7 (3) | C3—C23—C24—C25 | 47.7 (5) |
C36—N2—C8—C9 | 42.5 (4) | C3—C23—C24—C29 | −137.7 (3) |
C7—N2—C8—C5 | 33.3 (3) | C29—C24—C25—C26 | 1.2 (5) |
C36—N2—C8—C5 | 163.5 (3) | C23—C24—C25—C26 | 175.9 (3) |
C1—C5—C8—N2 | −129.2 (3) | C24—C25—C26—C27 | 0.4 (6) |
C4—C5—C8—N2 | 112.0 (3) | C25—C26—C27—C28 | −1.4 (6) |
C6—C5—C8—N2 | −6.4 (3) | C26—C27—C28—C29 | 0.8 (6) |
C1—C5—C8—C11 | 107.5 (3) | C27—C28—C29—C24 | 0.9 (6) |
C4—C5—C8—C11 | −11.3 (4) | C25—C24—C29—C28 | −1.8 (5) |
C6—C5—C8—C11 | −129.6 (3) | C23—C24—C29—C28 | −176.6 (3) |
C1—C5—C8—C9 | −8.7 (4) | C7—C6—C30—C35 | −13.2 (5) |
C4—C5—C8—C9 | −127.5 (3) | C5—C6—C30—C35 | 109.6 (4) |
C6—C5—C8—C9 | 114.2 (3) | C7—C6—C30—C31 | 165.0 (4) |
C10—N3—C9—O1 | −175.9 (3) | C5—C6—C30—C31 | −72.1 (4) |
C10—N3—C9—C8 | −1.1 (4) | C35—C30—C31—C32 | −0.9 (6) |
N2—C8—C9—O1 | 55.3 (4) | C6—C30—C31—C32 | −179.2 (4) |
C11—C8—C9—O1 | 173.5 (3) | C30—C31—C32—C33 | 0.9 (7) |
C5—C8—C9—O1 | −60.3 (4) | C31—C32—C33—C34 | −0.9 (8) |
N2—C8—C9—N3 | −119.4 (3) | C32—C33—C34—C35 | 0.9 (7) |
C11—C8—C9—N3 | −1.2 (3) | C31—C30—C35—C34 | 0.8 (6) |
C5—C8—C9—N3 | 125.0 (3) | C6—C30—C35—C34 | 179.1 (4) |
C9—N3—C10—C15 | −178.5 (3) | C33—C34—C35—C30 | −0.9 (7) |
C9—N3—C10—C11 | 3.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.86 | 1.99 | 2.835 (3) | 166 |
C1—H1A···O1 | 0.97 | 2.34 | 2.950 (4) | 120 |
C6—H6···O2 | 0.98 | 2.29 | 2.801 (4) | 111 |
C22—H22···N1 | 0.93 | 2.57 | 2.898 (5) | 101 |
C23—H23···O2 | 0.93 | 2.47 | 2.800 (4) | 101 |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C36H33N3O2 |
Mr | 539.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.535 (3), 11.441 (4), 15.682 (6) |
α, β, γ (°) | 102.027 (7), 92.423 (7), 100.637 (7) |
V (Å3) | 1466.8 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.16 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7663, 5152, 2883 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.181, 1.10 |
No. of reflections | 5152 |
No. of parameters | 372 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.25 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
N1—C16 | 1.468 (4) | N3—C10 | 1.403 (4) |
N2—C36 | 1.467 (4) | O1—C9 | 1.229 (3) |
C1—N1—C2 | 108.7 (2) | C8—N2—C36 | 115.4 (3) |
C7—N2—C8 | 107.0 (3) | O1—C9—N3 | 125.2 (3) |
C7—N2—C8—C5 | 33.3 (3) | C7—C6—C30—C35 | −13.2 (5) |
N2—C8—C9—N3 | −119.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.86 | 1.99 | 2.835 (3) | 166 |
C1—H1A···O1 | 0.97 | 2.34 | 2.950 (4) | 120 |
C6—H6···O2 | 0.98 | 2.29 | 2.801 (4) | 111 |
C22—H22···N1 | 0.93 | 2.57 | 2.898 (5) | 101 |
C23—H23···O2 | 0.93 | 2.47 | 2.800 (4) | 101 |
Symmetry code: (i) −x, −y+1, −z. |
Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important processes for the construction of spiro compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported.
There are dispiro rings in the molecule which consists of 2-oxindole, pyrrolidine and piperidone rings. The pyrrolidine ring (N2/C7/C6/C5/C8) is not planar, but shows an envelope conformation. The N2/C8/C5/C6 moiety is nearly planar and the mean deviation from this plane is 0.03 (1) Å. Atom C7 is shifted from the N2/C8/C5/C6 plane by 0.64 (2) Å. The dihedral angle between the N2/C7/C6 and N2/C8/C5/C6 planes is 43.4 (4)°. The dihedral angle between the C30—C36 phenyl plane and the N2/C8/C5/C6 plane is 63.9 (3)°. The 2-oxindole ring (C8/C9/N3/C10/C15/C14/C13/C12/C11) is nearly planar and the mean deviation from this plane is 0.03 (1) Å. The dihedral angle between the 2-oxindole ring mean plane and the N2/C8/C5/C6 plane is 86.9 (3)°. The piperidone ring has the usual chair conformation. In the crystal structure, there are intermolecular N—H···O hydrogen bonds (Fig. 2 and Table 2).