Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009516/cv6189sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009516/cv6189Isup2.hkl |
CCDC reference: 214824
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- Disorder in solvent or counterion
- R factor = 0.064
- wR factor = 0.196
- Data-to-parameter ratio = 14.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.697 0.909 Tmin' and Tmax expected: 0.887 0.909 RR' = 0.786 Please check that your absorption correction is appropriate. PLAT_302 Alert C Anion/Solvent Disorder ....................... 50.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
A mixture of 2,6-dichlorobenzonitrile oxide (3 mmol) and 1-benzyl-3,5-dibenzylidenepiperidin-4-one (1.5 mmol) in dry benzene (30 ml) was heated under reflux for 40 h. After evaporation of the solvent, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound, (I). M.p. 442–443 K; IR (KBr): 1736 (C═O), 1602, 1580 (C═N, C═C) cm−1; 1H NMR (CDCl3, p.p.m.): 2.42 (2H, d), 2.79 (2H, d), 3.10 (2H, m), 6.13 (2H, s), 6.94–7.37 (21H, m). 20 mg of (I) was dissolved in 15 ml chloroform, the solution was kept at room temperature for 10 d by natural evaporation to give colorless single crystals of (I) suitable for X-ray analysis.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT and SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C40H29Cl4N3O3·CHCl3 | Z = 2 |
Mr = 860.83 | F(000) = 880 |
Triclinic, P1 | Dx = 1.414 Mg m−3 |
a = 11.905 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.046 (17) Å | Cell parameters from 688 reflections |
c = 15.17 (2) Å | θ = 2.1–19.7° |
α = 87.89 (3)° | µ = 0.53 mm−1 |
β = 81.20 (3)° | T = 293 K |
γ = 70.20 (3)° | Plate, colorless |
V = 2022 (5) Å3 | 0.22 × 0.20 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 7038 independent reflections |
Radiation source: fine-focus sealed tube | 3463 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −14→13 |
Tmin = 0.697, Tmax = 0.909 | k = −14→10 |
10516 measured reflections | l = −18→16 |
Refinement on F2 | 78 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.196 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.35 e Å−3 |
7038 reflections | Δρmin = −0.31 e Å−3 |
504 parameters |
C40H29Cl4N3O3·CHCl3 | γ = 70.20 (3)° |
Mr = 860.83 | V = 2022 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.905 (18) Å | Mo Kα radiation |
b = 12.046 (17) Å | µ = 0.53 mm−1 |
c = 15.17 (2) Å | T = 293 K |
α = 87.89 (3)° | 0.22 × 0.20 × 0.18 mm |
β = 81.20 (3)° |
Bruker SMART CCD area-detector diffractometer | 7038 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 3463 reflections with I > 2σ(I) |
Tmin = 0.697, Tmax = 0.909 | Rint = 0.039 |
10516 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 78 restraints |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.35 e Å−3 |
7038 reflections | Δρmin = −0.31 e Å−3 |
504 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 | Occ. (<1) | |
Cl1 | 1.18974 (13) | −0.24329 (12) | 0.48262 (9) | 0.0670 (4) | |
Cl2 | 0.99328 (19) | −0.45635 (14) | 0.26948 (11) | 0.0965 (6) | |
Cl3 | 1.41005 (15) | 0.22579 (15) | 0.12547 (11) | 0.0862 (5) | |
Cl4 | 1.35066 (14) | −0.17778 (13) | 0.25401 (11) | 0.0800 (5) | |
O1 | 1.0840 (3) | 0.0054 (3) | 0.4048 (2) | 0.0516 (9) | |
O2 | 1.0159 (3) | −0.1084 (3) | 0.23324 (18) | 0.0434 (8) | |
O3 | 1.1101 (3) | 0.1922 (3) | 0.31799 (19) | 0.0456 (8) | |
N1 | 0.8665 (3) | 0.1345 (3) | 0.2263 (2) | 0.0436 (10) | |
N2 | 1.0754 (3) | −0.2248 (3) | 0.2582 (2) | 0.0444 (10) | |
N3 | 1.2365 (4) | 0.1483 (3) | 0.2918 (3) | 0.0483 (10) | |
C1 | 1.0391 (4) | 0.0257 (4) | 0.3380 (3) | 0.0369 (11) | |
C2 | 0.9537 (4) | −0.0377 (4) | 0.3142 (3) | 0.0366 (11) | |
C3 | 0.8374 (4) | 0.0546 (4) | 0.2933 (3) | 0.0449 (12) | |
H3A | 0.7875 | 0.0161 | 0.2711 | 0.054* | |
H3B | 0.7926 | 0.0987 | 0.3471 | 0.054* | |
C4 | 0.9309 (4) | 0.2034 (4) | 0.2596 (3) | 0.0432 (12) | |
H4A | 0.8865 | 0.2423 | 0.3155 | 0.052* | |
H4B | 0.9383 | 0.2635 | 0.2170 | 0.052* | |
C5 | 1.0559 (4) | 0.1219 (4) | 0.2741 (3) | 0.0383 (11) | |
C6 | 0.9397 (4) | −0.1284 (4) | 0.3841 (3) | 0.0380 (11) | |
H6 | 0.9625 | −0.1102 | 0.4399 | 0.046* | |
C7 | 1.0377 (4) | −0.2370 (4) | 0.3401 (3) | 0.0409 (11) | |
C8 | 1.1497 (4) | 0.0693 (4) | 0.1902 (3) | 0.0378 (11) | |
H8 | 1.1599 | −0.0142 | 0.1827 | 0.045* | |
C9 | 1.2585 (4) | 0.0804 (4) | 0.2236 (3) | 0.0415 (11) | |
C10 | 1.0853 (4) | −0.3521 (4) | 0.3835 (3) | 0.0470 (12) | |
C11 | 1.1506 (4) | −0.3619 (4) | 0.4538 (3) | 0.0519 (13) | |
C12 | 1.1937 (5) | −0.4649 (5) | 0.4990 (4) | 0.0681 (16) | |
H12 | 1.2360 | −0.4678 | 0.5463 | 0.082* | |
C13 | 1.1730 (5) | −0.5641 (5) | 0.4728 (5) | 0.0787 (19) | |
H13 | 1.2003 | −0.6342 | 0.5033 | 0.094* | |
C14 | 1.1124 (6) | −0.5597 (5) | 0.4021 (4) | 0.0758 (19) | |
H14 | 1.1009 | −0.6274 | 0.3838 | 0.091* | |
C15 | 1.0686 (5) | −0.4553 (4) | 0.3580 (3) | 0.0595 (14) | |
C16 | 0.8170 (4) | −0.1437 (4) | 0.4036 (3) | 0.0388 (11) | |
C17 | 0.7482 (4) | −0.1142 (4) | 0.4858 (3) | 0.0450 (12) | |
H17 | 0.7785 | −0.0867 | 0.5303 | 0.054* | |
C18 | 0.6351 (5) | −0.1243 (5) | 0.5041 (4) | 0.0636 (15) | |
H18 | 0.5903 | −0.1042 | 0.5605 | 0.076* | |
C19 | 0.5885 (5) | −0.1634 (5) | 0.4401 (5) | 0.0715 (17) | |
H19 | 0.5118 | −0.1693 | 0.4524 | 0.086* | |
C20 | 0.6557 (6) | −0.1942 (5) | 0.3566 (4) | 0.0719 (17) | |
H20 | 0.6244 | −0.2212 | 0.3126 | 0.086* | |
C21 | 0.7692 (5) | −0.1849 (5) | 0.3388 (3) | 0.0596 (14) | |
H21 | 0.8145 | −0.2065 | 0.2826 | 0.072* | |
C22 | 0.7601 (5) | 0.2097 (5) | 0.1872 (3) | 0.0615 (15) | |
H22A | 0.7202 | 0.1594 | 0.1667 | 0.074* | |
H22B | 0.7877 | 0.2484 | 0.1354 | 0.074* | |
C23 | 0.6691 (5) | 0.3024 (5) | 0.2497 (3) | 0.0565 (14) | |
C24 | 0.6760 (6) | 0.4151 (6) | 0.2546 (4) | 0.0802 (19) | |
H24 | 0.7368 | 0.4339 | 0.2177 | 0.096* | |
C25 | 0.5938 (7) | 0.4999 (7) | 0.3137 (6) | 0.105 (3) | |
H25 | 0.5999 | 0.5746 | 0.3162 | 0.126* | |
C26 | 0.5057 (9) | 0.4744 (9) | 0.3669 (6) | 0.127 (3) | |
H26 | 0.4512 | 0.5311 | 0.4069 | 0.153* | |
C27 | 0.4961 (7) | 0.3656 (9) | 0.3625 (6) | 0.130 (4) | |
H27 | 0.4336 | 0.3493 | 0.3991 | 0.156* | |
C28 | 0.5771 (6) | 0.2781 (6) | 0.3048 (5) | 0.087 (2) | |
H28 | 0.5694 | 0.2039 | 0.3034 | 0.104* | |
C29 | 1.3846 (4) | 0.0175 (4) | 0.1815 (3) | 0.0470 (12) | |
C30 | 1.4582 (5) | 0.0755 (5) | 0.1330 (3) | 0.0600 (15) | |
C31 | 1.5715 (5) | 0.0095 (7) | 0.0886 (4) | 0.0793 (19) | |
H31 | 1.6204 | 0.0477 | 0.0565 | 0.095* | |
C32 | 1.6117 (5) | −0.1115 (7) | 0.0917 (4) | 0.086 (2) | |
H32 | 1.6866 | −0.1544 | 0.0603 | 0.103* | |
C33 | 1.5426 (5) | −0.1702 (6) | 0.1408 (4) | 0.0723 (17) | |
H33 | 1.5703 | −0.2522 | 0.1431 | 0.087* | |
C34 | 1.4324 (5) | −0.1053 (5) | 0.1860 (3) | 0.0544 (13) | |
C35 | 1.1245 (4) | 0.1333 (4) | 0.1040 (3) | 0.0435 (12) | |
C36 | 1.1149 (4) | 0.2505 (5) | 0.0925 (3) | 0.0545 (13) | |
H36 | 1.1298 | 0.2918 | 0.1374 | 0.065* | |
C37 | 1.0834 (5) | 0.3058 (5) | 0.0151 (4) | 0.0721 (17) | |
H37 | 1.0760 | 0.3849 | 0.0082 | 0.086* | |
C38 | 1.0623 (5) | 0.2457 (7) | −0.0532 (4) | 0.081 (2) | |
H38 | 1.0399 | 0.2845 | −0.1052 | 0.098* | |
C39 | 1.0742 (5) | 0.1304 (7) | −0.0441 (3) | 0.080 (2) | |
H39 | 1.0619 | 0.0896 | −0.0905 | 0.096* | |
C40 | 1.1049 (4) | 0.0723 (5) | 0.0348 (3) | 0.0577 (14) | |
H40 | 1.1123 | −0.0068 | 0.0411 | 0.069* | |
C41 | 0.2860 (7) | 0.6084 (6) | 0.0946 (5) | 0.083 (2) | 0.810 (10) |
H41A | 0.2138 | 0.6608 | 0.1315 | 0.100* | 0.810 (10) |
Cl5 | 0.3587 (6) | 0.6925 (5) | 0.0280 (3) | 0.1390 (17) | 0.810 (10) |
Cl6 | 0.2439 (4) | 0.5187 (3) | 0.0265 (3) | 0.1287 (14) | 0.810 (10) |
Cl7 | 0.3856 (7) | 0.5236 (4) | 0.1627 (4) | 0.169 (2) | 0.810 (10) |
C41' | 0.2557 (19) | 0.6032 (14) | 0.0890 (11) | 0.096 (5)* | 0.190 (10) |
H41B | 0.1698 | 0.6255 | 0.1133 | 0.115* | 0.190 (10) |
Cl5' | 0.2894 (15) | 0.7305 (9) | 0.0482 (8) | 0.091 (4)* | 0.190 (10) |
Cl6' | 0.291 (2) | 0.4992 (15) | 0.0007 (12) | 0.151 (7)* | 0.190 (10) |
Cl7' | 0.3440 (13) | 0.5394 (13) | 0.1737 (8) | 0.071 (4)* | 0.190 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0747 (10) | 0.0601 (9) | 0.0689 (9) | −0.0187 (7) | −0.0293 (7) | 0.0056 (7) |
Cl2 | 0.1501 (17) | 0.0663 (10) | 0.0929 (12) | −0.0522 (11) | −0.0389 (11) | −0.0077 (9) |
Cl3 | 0.0874 (12) | 0.0905 (12) | 0.0955 (12) | −0.0539 (10) | −0.0053 (9) | 0.0128 (9) |
Cl4 | 0.0738 (10) | 0.0567 (9) | 0.0994 (12) | −0.0112 (8) | −0.0115 (9) | 0.0183 (8) |
O1 | 0.070 (2) | 0.058 (2) | 0.0379 (18) | −0.0308 (18) | −0.0218 (17) | 0.0097 (16) |
O2 | 0.062 (2) | 0.0414 (19) | 0.0292 (16) | −0.0206 (16) | −0.0076 (15) | −0.0017 (14) |
O3 | 0.054 (2) | 0.0424 (19) | 0.0435 (18) | −0.0213 (16) | −0.0018 (16) | −0.0069 (15) |
N1 | 0.047 (2) | 0.046 (2) | 0.039 (2) | −0.0149 (19) | −0.0137 (18) | 0.0102 (18) |
N2 | 0.058 (3) | 0.036 (2) | 0.041 (2) | −0.019 (2) | −0.005 (2) | −0.0003 (18) |
N3 | 0.054 (3) | 0.054 (3) | 0.043 (2) | −0.027 (2) | −0.007 (2) | 0.000 (2) |
C1 | 0.040 (3) | 0.036 (3) | 0.032 (3) | −0.010 (2) | −0.003 (2) | −0.004 (2) |
C2 | 0.050 (3) | 0.036 (3) | 0.026 (2) | −0.015 (2) | −0.007 (2) | 0.000 (2) |
C3 | 0.048 (3) | 0.047 (3) | 0.043 (3) | −0.020 (2) | −0.013 (2) | 0.007 (2) |
C4 | 0.052 (3) | 0.034 (3) | 0.040 (3) | −0.011 (2) | −0.004 (2) | 0.002 (2) |
C5 | 0.045 (3) | 0.038 (3) | 0.035 (2) | −0.018 (2) | −0.005 (2) | 0.000 (2) |
C6 | 0.048 (3) | 0.038 (3) | 0.030 (2) | −0.016 (2) | −0.010 (2) | 0.000 (2) |
C7 | 0.051 (3) | 0.040 (3) | 0.037 (3) | −0.020 (2) | −0.011 (2) | −0.001 (2) |
C8 | 0.043 (3) | 0.039 (3) | 0.034 (2) | −0.016 (2) | −0.008 (2) | −0.001 (2) |
C9 | 0.048 (3) | 0.046 (3) | 0.035 (3) | −0.020 (2) | −0.011 (2) | 0.008 (2) |
C10 | 0.048 (3) | 0.042 (3) | 0.043 (3) | −0.009 (2) | 0.004 (2) | −0.003 (2) |
C11 | 0.047 (3) | 0.048 (3) | 0.053 (3) | −0.005 (2) | −0.010 (3) | 0.007 (3) |
C12 | 0.060 (4) | 0.057 (4) | 0.070 (4) | 0.000 (3) | −0.008 (3) | 0.015 (3) |
C13 | 0.070 (4) | 0.049 (4) | 0.093 (5) | 0.005 (3) | −0.003 (4) | 0.018 (3) |
C14 | 0.083 (5) | 0.033 (3) | 0.098 (5) | −0.012 (3) | 0.012 (4) | −0.008 (3) |
C15 | 0.070 (4) | 0.047 (3) | 0.059 (3) | −0.017 (3) | −0.004 (3) | −0.010 (3) |
C16 | 0.049 (3) | 0.037 (3) | 0.034 (2) | −0.018 (2) | −0.012 (2) | 0.006 (2) |
C17 | 0.048 (3) | 0.046 (3) | 0.042 (3) | −0.016 (2) | −0.009 (2) | 0.009 (2) |
C18 | 0.049 (3) | 0.068 (4) | 0.070 (4) | −0.018 (3) | −0.001 (3) | 0.005 (3) |
C19 | 0.051 (4) | 0.078 (4) | 0.094 (5) | −0.031 (3) | −0.018 (4) | 0.017 (4) |
C20 | 0.084 (4) | 0.070 (4) | 0.085 (5) | −0.045 (4) | −0.040 (4) | 0.015 (3) |
C21 | 0.072 (4) | 0.071 (4) | 0.049 (3) | −0.039 (3) | −0.015 (3) | 0.001 (3) |
C22 | 0.071 (4) | 0.064 (4) | 0.054 (3) | −0.022 (3) | −0.025 (3) | 0.018 (3) |
C23 | 0.044 (3) | 0.059 (4) | 0.060 (3) | −0.005 (3) | −0.022 (3) | 0.015 (3) |
C24 | 0.063 (4) | 0.063 (4) | 0.104 (5) | −0.004 (3) | −0.022 (4) | 0.012 (4) |
C25 | 0.082 (5) | 0.075 (5) | 0.139 (7) | 0.005 (5) | −0.030 (5) | −0.012 (5) |
C26 | 0.101 (7) | 0.111 (8) | 0.125 (7) | 0.020 (6) | −0.007 (6) | −0.005 (6) |
C27 | 0.070 (5) | 0.144 (8) | 0.126 (7) | 0.006 (6) | 0.025 (5) | 0.042 (7) |
C28 | 0.056 (4) | 0.082 (5) | 0.108 (5) | −0.010 (4) | −0.005 (4) | 0.024 (4) |
C29 | 0.042 (3) | 0.064 (4) | 0.039 (3) | −0.022 (3) | −0.008 (2) | 0.000 (2) |
C30 | 0.053 (3) | 0.085 (4) | 0.049 (3) | −0.031 (3) | −0.011 (3) | 0.000 (3) |
C31 | 0.052 (4) | 0.131 (6) | 0.062 (4) | −0.041 (4) | −0.004 (3) | 0.001 (4) |
C32 | 0.045 (4) | 0.116 (6) | 0.079 (5) | −0.003 (4) | −0.005 (3) | −0.020 (4) |
C33 | 0.048 (4) | 0.083 (4) | 0.076 (4) | −0.007 (3) | −0.013 (3) | −0.010 (4) |
C34 | 0.048 (3) | 0.060 (4) | 0.054 (3) | −0.016 (3) | −0.008 (3) | 0.001 (3) |
C35 | 0.037 (3) | 0.058 (3) | 0.034 (3) | −0.017 (2) | 0.001 (2) | −0.001 (2) |
C36 | 0.058 (3) | 0.055 (3) | 0.052 (3) | −0.020 (3) | −0.010 (3) | 0.012 (3) |
C37 | 0.058 (4) | 0.076 (4) | 0.071 (4) | −0.013 (3) | −0.007 (3) | 0.034 (4) |
C38 | 0.059 (4) | 0.129 (6) | 0.061 (4) | −0.035 (4) | −0.026 (3) | 0.044 (4) |
C39 | 0.067 (4) | 0.150 (7) | 0.038 (3) | −0.053 (4) | −0.019 (3) | 0.014 (4) |
C40 | 0.053 (3) | 0.084 (4) | 0.046 (3) | −0.039 (3) | 0.000 (3) | −0.003 (3) |
C41 | 0.079 (5) | 0.075 (4) | 0.090 (5) | −0.020 (4) | −0.008 (4) | 0.000 (4) |
Cl5 | 0.171 (5) | 0.178 (4) | 0.103 (2) | −0.105 (4) | −0.027 (3) | 0.039 (2) |
Cl6 | 0.109 (3) | 0.120 (2) | 0.166 (3) | −0.039 (2) | −0.036 (2) | −0.038 (2) |
Cl7 | 0.229 (6) | 0.096 (2) | 0.171 (3) | −0.003 (3) | −0.120 (4) | 0.011 (2) |
Cl1—C11 | 1.735 (6) | C19—C20 | 1.379 (8) |
Cl2—C15 | 1.727 (6) | C19—H19 | 0.9300 |
Cl3—C30 | 1.709 (6) | C20—C21 | 1.379 (8) |
Cl4—C34 | 1.725 (6) | C20—H20 | 0.9300 |
O1—C1 | 1.196 (5) | C21—H21 | 0.9300 |
O2—N2 | 1.407 (5) | C22—C23 | 1.504 (7) |
O2—C2 | 1.468 (5) | C22—H22A | 0.9700 |
O3—N3 | 1.413 (5) | C22—H22B | 0.9700 |
O3—C5 | 1.456 (5) | C23—C28 | 1.380 (8) |
N1—C4 | 1.453 (6) | C23—C24 | 1.394 (8) |
N1—C3 | 1.458 (5) | C24—C25 | 1.387 (9) |
N1—C22 | 1.480 (6) | C24—H24 | 0.9300 |
N2—C7 | 1.276 (5) | C25—C26 | 1.336 (11) |
N3—C9 | 1.280 (6) | C25—H25 | 0.9300 |
C1—C5 | 1.529 (6) | C26—C27 | 1.359 (12) |
C1—C2 | 1.550 (6) | C26—H26 | 0.9300 |
C2—C3 | 1.523 (6) | C27—C28 | 1.387 (10) |
C2—C6 | 1.527 (6) | C27—H27 | 0.9300 |
C3—H3A | 0.9700 | C28—H28 | 0.9300 |
C3—H3B | 0.9700 | C29—C34 | 1.397 (7) |
C4—C5 | 1.523 (6) | C29—C30 | 1.406 (7) |
C4—H4A | 0.9700 | C30—C31 | 1.393 (8) |
C4—H4B | 0.9700 | C31—C32 | 1.373 (9) |
C5—C8 | 1.553 (6) | C31—H31 | 0.9300 |
C6—C16 | 1.517 (6) | C32—C33 | 1.377 (8) |
C6—C7 | 1.520 (6) | C32—H32 | 0.9300 |
C6—H6 | 0.9800 | C33—C34 | 1.368 (7) |
C7—C10 | 1.480 (7) | C33—H33 | 0.9300 |
C8—C9 | 1.508 (6) | C35—C36 | 1.384 (7) |
C8—C35 | 1.511 (6) | C35—C40 | 1.395 (7) |
C8—H8 | 0.9800 | C36—C37 | 1.367 (7) |
C9—C29 | 1.486 (7) | C36—H36 | 0.9300 |
C10—C11 | 1.392 (7) | C37—C38 | 1.385 (9) |
C10—C15 | 1.400 (7) | C37—H37 | 0.9300 |
C11—C12 | 1.373 (7) | C38—C39 | 1.351 (9) |
C12—C13 | 1.384 (9) | C38—H38 | 0.9300 |
C12—H12 | 0.9300 | C39—C40 | 1.397 (8) |
C13—C14 | 1.370 (9) | C39—H39 | 0.9300 |
C13—H13 | 0.9300 | C40—H40 | 0.9300 |
C14—C15 | 1.380 (8) | C41—Cl7 | 1.730 (7) |
C14—H14 | 0.9300 | C41—Cl5 | 1.746 (7) |
C16—C17 | 1.369 (6) | C41—Cl6 | 1.759 (7) |
C16—C21 | 1.391 (6) | C41—H41A | 0.9800 |
C17—C18 | 1.379 (7) | C41'—Cl6' | 1.770 (11) |
C17—H17 | 0.9300 | C41'—Cl7' | 1.772 (11) |
C18—C19 | 1.358 (8) | C41'—Cl5' | 1.779 (11) |
C18—H18 | 0.9300 | C41'—H41B | 0.9800 |
N2—O2—C2 | 108.6 (3) | C18—C19—H19 | 120.2 |
N3—O3—C5 | 108.8 (3) | C20—C19—H19 | 120.2 |
C4—N1—C3 | 112.0 (4) | C19—C20—C21 | 119.8 (5) |
C4—N1—C22 | 112.1 (4) | C19—C20—H20 | 120.1 |
C3—N1—C22 | 112.9 (4) | C21—C20—H20 | 120.1 |
C7—N2—O2 | 108.8 (3) | C20—C21—C16 | 120.9 (5) |
C9—N3—O3 | 107.8 (4) | C20—C21—H21 | 119.5 |
O1—C1—C5 | 121.7 (4) | C16—C21—H21 | 119.5 |
O1—C1—C2 | 122.2 (4) | N1—C22—C23 | 114.7 (4) |
C5—C1—C2 | 115.9 (4) | N1—C22—H22A | 108.6 |
O2—C2—C3 | 108.8 (3) | C23—C22—H22A | 108.6 |
O2—C2—C6 | 104.3 (3) | N1—C22—H22B | 108.6 |
C3—C2—C6 | 116.3 (4) | C23—C22—H22B | 108.6 |
O2—C2—C1 | 106.3 (3) | H22A—C22—H22B | 107.6 |
C3—C2—C1 | 109.0 (4) | C28—C23—C24 | 117.8 (6) |
C6—C2—C1 | 111.5 (4) | C28—C23—C22 | 121.1 (6) |
N1—C3—C2 | 109.4 (4) | C24—C23—C22 | 121.0 (5) |
N1—C3—H3A | 109.8 | C25—C24—C23 | 121.1 (7) |
C2—C3—H3A | 109.8 | C25—C24—H24 | 119.5 |
N1—C3—H3B | 109.8 | C23—C24—H24 | 119.5 |
C2—C3—H3B | 109.8 | C26—C25—C24 | 120.2 (8) |
H3A—C3—H3B | 108.2 | C26—C25—H25 | 119.9 |
N1—C4—C5 | 109.3 (4) | C24—C25—H25 | 119.9 |
N1—C4—H4A | 109.8 | C25—C26—C27 | 119.8 (9) |
C5—C4—H4A | 109.8 | C25—C26—H26 | 120.1 |
N1—C4—H4B | 109.8 | C27—C26—H26 | 120.1 |
C5—C4—H4B | 109.8 | C26—C27—C28 | 121.8 (8) |
H4A—C4—H4B | 108.3 | C26—C27—H27 | 119.1 |
O3—C5—C4 | 106.9 (4) | C28—C27—H27 | 119.1 |
O3—C5—C1 | 108.3 (3) | C23—C28—C27 | 119.3 (7) |
C4—C5—C1 | 107.6 (4) | C23—C28—H28 | 120.4 |
O3—C5—C8 | 104.0 (3) | C27—C28—H28 | 120.4 |
C4—C5—C8 | 117.8 (4) | C34—C29—C30 | 117.4 (5) |
C1—C5—C8 | 111.7 (4) | C34—C29—C9 | 119.6 (4) |
C16—C6—C7 | 112.8 (4) | C30—C29—C9 | 122.9 (5) |
C16—C6—C2 | 116.8 (4) | C31—C30—C29 | 119.6 (6) |
C7—C6—C2 | 98.7 (3) | C31—C30—Cl3 | 119.2 (5) |
C16—C6—H6 | 109.3 | C29—C30—Cl3 | 121.2 (4) |
C7—C6—H6 | 109.3 | C32—C31—C30 | 120.6 (6) |
C2—C6—H6 | 109.3 | C32—C31—H31 | 119.7 |
N2—C7—C10 | 120.1 (4) | C30—C31—H31 | 119.7 |
N2—C7—C6 | 114.6 (4) | C31—C32—C33 | 120.9 (6) |
C10—C7—C6 | 125.2 (4) | C31—C32—H32 | 119.5 |
C9—C8—C35 | 113.1 (4) | C33—C32—H32 | 119.5 |
C9—C8—C5 | 97.5 (3) | C34—C33—C32 | 118.6 (6) |
C35—C8—C5 | 115.9 (4) | C34—C33—H33 | 120.7 |
C9—C8—H8 | 109.9 | C32—C33—H33 | 120.7 |
C35—C8—H8 | 109.9 | C33—C34—C29 | 122.8 (5) |
C5—C8—H8 | 109.9 | C33—C34—Cl4 | 118.6 (5) |
N3—C9—C29 | 120.8 (4) | C29—C34—Cl4 | 118.5 (4) |
N3—C9—C8 | 115.9 (4) | C36—C35—C40 | 119.0 (5) |
C29—C9—C8 | 123.2 (4) | C36—C35—C8 | 122.9 (4) |
C11—C10—C15 | 116.4 (5) | C40—C35—C8 | 118.0 (5) |
C11—C10—C7 | 120.1 (4) | C37—C36—C35 | 120.1 (5) |
C15—C10—C7 | 123.5 (5) | C37—C36—H36 | 120.0 |
C12—C11—C10 | 123.1 (5) | C35—C36—H36 | 120.0 |
C12—C11—Cl1 | 117.0 (5) | C36—C37—C38 | 120.9 (6) |
C10—C11—Cl1 | 119.8 (4) | C36—C37—H37 | 119.5 |
C11—C12—C13 | 118.5 (6) | C38—C37—H37 | 119.5 |
C11—C12—H12 | 120.7 | C39—C38—C37 | 119.9 (6) |
C13—C12—H12 | 120.7 | C39—C38—H38 | 120.1 |
C14—C13—C12 | 120.4 (5) | C37—C38—H38 | 120.1 |
C14—C13—H13 | 119.8 | C38—C39—C40 | 120.3 (6) |
C12—C13—H13 | 119.8 | C38—C39—H39 | 119.9 |
C13—C14—C15 | 120.3 (6) | C40—C39—H39 | 119.9 |
C13—C14—H14 | 119.9 | C35—C40—C39 | 119.8 (6) |
C15—C14—H14 | 119.9 | C35—C40—H40 | 120.1 |
C14—C15—C10 | 121.2 (5) | C39—C40—H40 | 120.1 |
C14—C15—Cl2 | 117.7 (5) | Cl7—C41—Cl5 | 107.6 (4) |
C10—C15—Cl2 | 121.1 (4) | Cl7—C41—Cl6 | 111.0 (4) |
C17—C16—C21 | 117.8 (5) | Cl5—C41—Cl6 | 109.6 (4) |
C17—C16—C6 | 120.5 (4) | Cl7—C41—H41A | 109.5 |
C21—C16—C6 | 121.7 (4) | Cl5—C41—H41A | 109.5 |
C16—C17—C18 | 121.4 (5) | Cl6—C41—H41A | 109.5 |
C16—C17—H17 | 119.3 | Cl6'—C41'—Cl7' | 109.1 (9) |
C18—C17—H17 | 119.3 | Cl6'—C41'—Cl5' | 109.3 (9) |
C19—C18—C17 | 120.4 (5) | Cl7'—C41'—Cl5' | 109.3 (8) |
C19—C18—H18 | 119.8 | Cl6'—C41'—H41B | 109.7 |
C17—C18—H18 | 119.8 | Cl7'—C41'—H41B | 109.7 |
C18—C19—C20 | 119.6 (6) | Cl5'—C41'—H41B | 109.7 |
C2—O2—N2—C7 | 12.5 (5) | Cl1—C11—C12—C13 | −174.6 (4) |
C5—O3—N3—C9 | 14.6 (4) | C11—C12—C13—C14 | 1.1 (9) |
N2—O2—C2—C3 | −146.2 (3) | C12—C13—C14—C15 | −1.8 (9) |
N2—O2—C2—C6 | −21.4 (4) | C13—C14—C15—C10 | 0.5 (9) |
N2—O2—C2—C1 | 96.6 (4) | C13—C14—C15—Cl2 | 180.0 (5) |
O1—C1—C2—O2 | −114.9 (4) | C11—C10—C15—C14 | 1.5 (7) |
C5—C1—C2—O2 | 69.2 (4) | C7—C10—C15—C14 | −178.4 (5) |
O1—C1—C2—C3 | 128.0 (4) | C11—C10—C15—Cl2 | −178.0 (4) |
C5—C1—C2—C3 | −48.0 (5) | C7—C10—C15—Cl2 | 2.1 (7) |
O1—C1—C2—C6 | −1.8 (6) | C7—C6—C16—C17 | 131.8 (4) |
C5—C1—C2—C6 | −177.8 (3) | C2—C6—C16—C17 | −114.8 (5) |
C4—N1—C3—C2 | −65.3 (5) | C7—C6—C16—C21 | −49.7 (6) |
C22—N1—C3—C2 | 167.0 (4) | C2—C6—C16—C21 | 63.6 (6) |
O2—C2—C3—N1 | −63.2 (4) | C21—C16—C17—C18 | −0.3 (7) |
C6—C2—C3—N1 | 179.5 (3) | C6—C16—C17—C18 | 178.2 (4) |
C1—C2—C3—N1 | 52.3 (5) | C16—C17—C18—C19 | −0.4 (8) |
C3—N1—C4—C5 | 67.9 (4) | C17—C18—C19—C20 | 0.7 (8) |
C22—N1—C4—C5 | −164.0 (4) | C18—C19—C20—C21 | −0.1 (9) |
N3—O3—C5—C4 | −149.1 (3) | C19—C20—C21—C16 | −0.6 (8) |
N3—O3—C5—C1 | 95.2 (4) | C17—C16—C21—C20 | 0.8 (7) |
N3—O3—C5—C8 | −23.8 (4) | C6—C16—C21—C20 | −177.6 (5) |
N1—C4—C5—O3 | −172.8 (3) | C4—N1—C22—C23 | −57.7 (6) |
N1—C4—C5—C1 | −56.7 (4) | C3—N1—C22—C23 | 69.9 (6) |
N1—C4—C5—C8 | 70.7 (5) | N1—C22—C23—C28 | −88.1 (6) |
O1—C1—C5—O3 | −11.2 (6) | N1—C22—C23—C24 | 91.0 (6) |
C2—C1—C5—O3 | 164.8 (3) | C28—C23—C24—C25 | 0.6 (9) |
O1—C1—C5—C4 | −126.4 (4) | C22—C23—C24—C25 | −178.5 (5) |
C2—C1—C5—C4 | 49.6 (5) | C23—C24—C25—C26 | −0.2 (11) |
O1—C1—C5—C8 | 102.8 (5) | C24—C25—C26—C27 | −0.7 (14) |
C2—C1—C5—C8 | −81.2 (5) | C25—C26—C27—C28 | 1.2 (15) |
O2—C2—C6—C16 | −100.7 (4) | C24—C23—C28—C27 | −0.1 (9) |
C3—C2—C6—C16 | 19.1 (5) | C22—C23—C28—C27 | 179.0 (6) |
C1—C2—C6—C16 | 145.0 (4) | C26—C27—C28—C23 | −0.8 (12) |
O2—C2—C6—C7 | 20.4 (4) | N3—C9—C29—C34 | 112.5 (5) |
C3—C2—C6—C7 | 140.2 (4) | C8—C9—C29—C34 | −67.4 (6) |
C1—C2—C6—C7 | −93.9 (4) | N3—C9—C29—C30 | −70.4 (6) |
O2—N2—C7—C10 | 179.6 (4) | C8—C9—C29—C30 | 109.7 (5) |
O2—N2—C7—C6 | 2.3 (5) | C34—C29—C30—C31 | 3.0 (7) |
C16—C6—C7—N2 | 109.1 (4) | C9—C29—C30—C31 | −174.1 (5) |
C2—C6—C7—N2 | −14.9 (5) | C34—C29—C30—Cl3 | −178.4 (4) |
C16—C6—C7—C10 | −68.1 (6) | C9—C29—C30—Cl3 | 4.5 (7) |
C2—C6—C7—C10 | 167.9 (4) | C29—C30—C31—C32 | 0.1 (8) |
O3—C5—C8—C9 | 22.0 (4) | Cl3—C30—C31—C32 | −178.6 (5) |
C4—C5—C8—C9 | 140.0 (4) | C30—C31—C32—C33 | −1.8 (10) |
C1—C5—C8—C9 | −94.6 (4) | C31—C32—C33—C34 | 0.4 (9) |
O3—C5—C8—C35 | −98.3 (4) | C32—C33—C34—C29 | 2.9 (8) |
C4—C5—C8—C35 | 19.7 (6) | C32—C33—C34—Cl4 | −175.3 (5) |
C1—C5—C8—C35 | 145.1 (4) | C30—C29—C34—C33 | −4.6 (8) |
O3—N3—C9—C29 | −178.3 (4) | C9—C29—C34—C33 | 172.6 (5) |
O3—N3—C9—C8 | 1.6 (5) | C30—C29—C34—Cl4 | 173.6 (4) |
C35—C8—C9—N3 | 107.0 (5) | C9—C29—C34—Cl4 | −9.1 (6) |
C5—C8—C9—N3 | −15.4 (5) | C9—C8—C35—C36 | −51.9 (6) |
C35—C8—C9—C29 | −73.2 (6) | C5—C8—C35—C36 | 59.6 (6) |
C5—C8—C9—C29 | 164.5 (4) | C9—C8—C35—C40 | 131.1 (4) |
N2—C7—C10—C11 | 116.3 (5) | C5—C8—C35—C40 | −117.4 (5) |
C6—C7—C10—C11 | −66.6 (6) | C40—C35—C36—C37 | 1.7 (7) |
N2—C7—C10—C15 | −63.8 (7) | C8—C35—C36—C37 | −175.3 (4) |
C6—C7—C10—C15 | 113.2 (5) | C35—C36—C37—C38 | −0.9 (8) |
C15—C10—C11—C12 | −2.2 (7) | C36—C37—C38—C39 | −0.8 (9) |
C7—C10—C11—C12 | 177.7 (5) | C37—C38—C39—C40 | 1.5 (9) |
C15—C10—C11—Cl1 | 173.2 (4) | C36—C35—C40—C39 | −1.0 (7) |
C7—C10—C11—Cl1 | −6.9 (6) | C8—C35—C40—C39 | 176.2 (4) |
C10—C11—C12—C13 | 1.0 (8) | C38—C39—C40—C35 | −0.7 (8) |
Experimental details
Crystal data | |
Chemical formula | C40H29Cl4N3O3·CHCl3 |
Mr | 860.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 11.905 (18), 12.046 (17), 15.17 (2) |
α, β, γ (°) | 87.89 (3), 81.20 (3), 70.20 (3) |
V (Å3) | 2022 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.53 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.697, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10516, 7038, 3463 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.196, 1.07 |
No. of reflections | 7038 |
No. of parameters | 504 |
No. of restraints | 78 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.31 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT and SHELXTL (Bruker, 1998), SHELXTL (Bruker, 1998), SHELXTL.
O1—C1 | 1.196 (5) | N1—C4 | 1.453 (6) |
O2—N2 | 1.407 (5) | N2—C7 | 1.276 (5) |
O3—N3 | 1.413 (5) | N3—C9 | 1.280 (6) |
N2—O2—C2 | 108.6 (3) | C7—N2—O2 | 108.8 (3) |
N3—O3—C5 | 108.8 (3) | C9—N3—O3 | 107.8 (4) |
C4—N1—C3 | 112.0 (4) | ||
C2—O2—N2—C7 | 12.5 (5) | O1—C1—C2—C6 | −1.8 (6) |
C5—O3—N3—C9 | 14.6 (4) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
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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 process for the construction of spiro-compounds (Caramella & Grunanger., 1984). The structure of the title compound, (I), is reported here.
The molecular structure of (I) is illustrated in Fig. 1. (I) contains three spiro-linked rings, viz. a piperidin-4-one ring and two isoxazoline rings. The six-membered piperidin-4-one ring has the chair conformation. Attached to the isoxazoline rings are phenyl and 2,6-dichlorophenyl substituents.
The two isoxazoline rings (A and B) are non-planar, with envelope conformations. O2/N2/C7/C6 (ring A) and O3/N3/C9/C8 (ring B) form nearly planar arrangements, with mean derivations of 0.0088 and 0.0060 Å, respectively. The spiro-atom C2 lies 0.3436 (3) Å out from the plane of ring A and C5 is −0.3772 (3) Å out from the plane of ring B, forming the flaps of the envelopes. The dihedral angle between the C6/C2/O2 and O2/N2/C7/C6 mean planes is 21.9 (4)°. The same angle between the C8/C5/O3 and O3/N3/C9/C8 mean planes is 24.1 (4)°. The dihedral angle between the two substituted phenyl rings on ring A is 97.7 (3)°, while the same angle between the two substituted phenyl rings on ring B is 78.8 (3)°.