Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015423/su6032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015423/su6032Isup2.hkl |
CCDC reference: 222855
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.128
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT331_ALERT_2_B Small Av. Phenyl C-C Dist. C44 - C46_a = 1.35 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ..... 0.99 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .. ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) . 3.16 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) . 3.06 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang.. 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
A mixture of 1-benzyl-3,5-dibenzylidenepiperidin-4-one (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) was refluxed in methanol (80 ml) until the disappearance of the starting material, shown by thin-layer chromatography. After the reaction was complete the solvent was removed in vacuo and the residue separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the intermediate compound. This was then reacted with 2,6-dichlorobenzonitrile oxide in refluxing dry benzene for 24 h. The mixture was then cooled and filtered. Recrystalization from benzene–THF gave the title compound, (I). Further synthetic and other details are given in the CIF. Colourless crystals, suitable for X-ray analysis, were obtained by slow evaporation of a solution of (I) in chloroform–benzene.
The H atoms were introduced at calculated positions as riding atoms, with bond lengths of 0.93 (CH-aromatic), 0.98 (CH), 0.98 (CH3), and 0.86 Å (N—H). The displacement parameters were 1.2 (CH, NH) or 1.5 (CH3) times thoses of the parent atoms.
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.
C43H36Cl2N4O3·0.5C6H6 | F(000) = 1604 |
Mr = 766.71 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1017 reflections |
a = 19.005 (7) Å | θ = 2.4–22.6° |
b = 12.611 (4) Å | µ = 0.22 mm−1 |
c = 17.986 (6) Å | T = 293 K |
β = 115.937 (5)° | Plate, colourless |
V = 3877 (2) Å3 | 0.38 × 0.22 × 0.20 mm |
Z = 4 |
Bruker CCD area-detector diffractometer | 6770 independent reflections |
Radiation source: fine-focus sealed tube | 3692 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→20 |
Tmin = 0.945, Tmax = 0.958 | k = −8→14 |
15867 measured reflections | l = −16→21 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.19 e Å−3 |
6770 reflections | Δρmin = −0.27 e Å−3 |
497 parameters |
C43H36Cl2N4O3·0.5C6H6 | V = 3877 (2) Å3 |
Mr = 766.71 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.005 (7) Å | µ = 0.22 mm−1 |
b = 12.611 (4) Å | T = 293 K |
c = 17.986 (6) Å | 0.38 × 0.22 × 0.20 mm |
β = 115.937 (5)° |
Bruker CCD area-detector diffractometer | 6770 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3692 reflections with I > 2σ(I) |
Tmin = 0.945, Tmax = 0.958 | Rint = 0.055 |
15867 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.19 e Å−3 |
6770 reflections | Δρmin = −0.27 e Å−3 |
497 parameters |
Experimental. A mixture of 1-benzyl-3,5-dibenzylidene-piperidin-4-one(2 mmol), isatin (2 mmol) and sarcosine (2 mmol) was refluxed in methanol (80 ml) until the disappearance of the starting material as evidenced by the TLC. After the reaction was completed 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 intermediate compound, then reacted the intermediate compound with 2,6-dichlorobenzonitrile oxide in reflux dry benzene at reflux for 24 h, cooled and filtered, recrystalized from benzene-THF to give title compound (I). M.p 498–500 K; IR (KBr): 3493(N—H), 1694,1682 (C=O), cm−1; 1H-NMR(CDCl3, p.p.m.): 1.54–1.59 (1H, d), 2.13(3H, s), 2.28–2.33(1H, d.), 2.69–2.73(1H, d.), 3.09–3.17(1H, d.), 3.21–3.28 (1H, d), 3.38–3.49 (2H, m), 4.04 (1H, t), 4.46 (1H,t) 5.87(1H, s), 6.62–7.53 (22H, m), 7.70(1H,br). 20 mg of (I) was dissolved in 15 ml chloroform-benzene mixed solvent; 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. |
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. The H atoms were introduced at calculated positions as riding atoms, with bond lengths of 0.93(CH-aromatic), 0.98(CH), 0.98(CH3), and 0.86(N—H) Å. The displacement parameters were made equal to 1.2(CH, NH) or 1.5(CH3) times thoses of the parent atoms. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.47238 (5) | 0.54992 (8) | 0.72067 (6) | 0.0729 (3) | |
Cl2 | 0.18291 (5) | 0.39801 (6) | 0.65293 (6) | 0.0547 (3) | |
N1 | 0.27442 (15) | 0.8979 (2) | 0.32184 (15) | 0.0434 (7) | |
H1 | 0.2493 | 0.9066 | 0.2692 | 0.052* | |
N2 | 0.37791 (15) | 1.00461 (19) | 0.51041 (16) | 0.0429 (7) | |
N3 | 0.17091 (12) | 0.80949 (16) | 0.41109 (13) | 0.0296 (6) | |
N4 | 0.24324 (13) | 0.61690 (17) | 0.64265 (13) | 0.0318 (6) | |
O1 | 0.21792 (13) | 1.03250 (16) | 0.36281 (13) | 0.0500 (6) | |
O2 | 0.36875 (11) | 0.77894 (14) | 0.63040 (12) | 0.0392 (5) | |
O3 | 0.21158 (11) | 0.69358 (14) | 0.57922 (11) | 0.0334 (5) | |
C1 | 0.26226 (18) | 0.9576 (2) | 0.37851 (19) | 0.0372 (8) | |
C2 | 0.33232 (18) | 0.8214 (2) | 0.3591 (2) | 0.0387 (8) | |
C3 | 0.3609 (2) | 0.7505 (3) | 0.3213 (2) | 0.0567 (10) | |
H3 | 0.3400 | 0.7463 | 0.2640 | 0.068* | |
C4 | 0.4214 (2) | 0.6858 (3) | 0.3708 (3) | 0.0621 (10) | |
H4 | 0.4409 | 0.6361 | 0.3464 | 0.075* | |
C5 | 0.4538 (2) | 0.6930 (3) | 0.4558 (2) | 0.0543 (9) | |
H5 | 0.4951 | 0.6488 | 0.4880 | 0.065* | |
C6 | 0.42488 (18) | 0.7664 (2) | 0.4937 (2) | 0.0425 (8) | |
H6 | 0.4473 | 0.7727 | 0.5510 | 0.051* | |
C7 | 0.36259 (16) | 0.8292 (2) | 0.44467 (18) | 0.0321 (7) | |
C8 | 0.32184 (17) | 0.9197 (2) | 0.46607 (17) | 0.0319 (7) | |
C9 | 0.3413 (2) | 1.0701 (2) | 0.5499 (2) | 0.0490 (9) | |
H9A | 0.2998 | 1.1131 | 0.5096 | 0.059* | |
H9B | 0.3793 | 1.1160 | 0.5913 | 0.059* | |
C10 | 0.30916 (17) | 0.9891 (2) | 0.58902 (17) | 0.0348 (7) | |
H10 | 0.3538 | 0.9620 | 0.6381 | 0.042* | |
C11 | 0.28085 (15) | 0.8961 (2) | 0.52446 (16) | 0.0292 (7) | |
C12 | 0.19205 (16) | 0.8872 (2) | 0.47711 (16) | 0.0298 (7) | |
H12A | 0.1703 | 0.8662 | 0.5147 | 0.036* | |
H12B | 0.1702 | 0.9557 | 0.4539 | 0.036* | |
C13 | 0.19978 (17) | 0.7023 (2) | 0.43903 (17) | 0.0350 (7) | |
H13A | 0.2253 | 0.6762 | 0.4062 | 0.042* | |
H13B | 0.1552 | 0.6566 | 0.4281 | 0.042* | |
C14 | 0.25643 (15) | 0.6924 (2) | 0.52942 (16) | 0.0275 (7) | |
C15 | 0.30967 (16) | 0.7892 (2) | 0.56673 (17) | 0.0274 (7) | |
C16 | 0.30354 (16) | 0.5878 (2) | 0.55477 (16) | 0.0284 (7) | |
H16 | 0.3588 | 0.6031 | 0.5706 | 0.034* | |
C17 | 0.29353 (16) | 0.5604 (2) | 0.63111 (16) | 0.0280 (7) | |
C18 | 0.4076 (2) | 1.0640 (3) | 0.4602 (2) | 0.0645 (11) | |
H18A | 0.3653 | 1.1017 | 0.4175 | 0.097* | |
H18B | 0.4304 | 1.0158 | 0.4356 | 0.097* | |
H18C | 0.4466 | 1.1136 | 0.4946 | 0.097* | |
C19 | 0.25062 (18) | 1.0296 (2) | 0.61794 (19) | 0.0399 (8) | |
C20 | 0.1904 (2) | 1.0987 (2) | 0.5725 (2) | 0.0548 (9) | |
H20 | 0.1858 | 1.1237 | 0.5219 | 0.066* | |
C21 | 0.1372 (2) | 1.1310 (3) | 0.6009 (3) | 0.0746 (13) | |
H21 | 0.0972 | 1.1774 | 0.5695 | 0.090* | |
C22 | 0.1432 (3) | 1.0952 (4) | 0.6748 (4) | 0.0864 (15) | |
H22 | 0.1068 | 1.1167 | 0.6934 | 0.104* | |
C23 | 0.2017 (3) | 1.0283 (3) | 0.7215 (3) | 0.0782 (13) | |
H23 | 0.2058 | 1.0045 | 0.7722 | 0.094* | |
C24 | 0.2556 (2) | 0.9955 (3) | 0.6934 (2) | 0.0562 (10) | |
H24 | 0.2958 | 0.9499 | 0.7258 | 0.067* | |
C25 | 0.08685 (17) | 0.8133 (2) | 0.35701 (18) | 0.0453 (8) | |
H25A | 0.0723 | 0.8863 | 0.3403 | 0.054* | |
H25B | 0.0591 | 0.7911 | 0.3885 | 0.054* | |
C26 | 0.06000 (18) | 0.7457 (2) | 0.28053 (19) | 0.0405 (8) | |
C27 | 0.1040 (2) | 0.7338 (3) | 0.2377 (2) | 0.0552 (9) | |
H27 | 0.1528 | 0.7662 | 0.2571 | 0.066* | |
C28 | 0.0769 (3) | 0.6744 (3) | 0.1660 (2) | 0.0698 (11) | |
H28 | 0.1073 | 0.6674 | 0.1375 | 0.084* | |
C29 | 0.0057 (3) | 0.6259 (3) | 0.1370 (2) | 0.0755 (13) | |
H29 | −0.0123 | 0.5853 | 0.0890 | 0.091* | |
C30 | −0.0389 (2) | 0.6370 (3) | 0.1781 (3) | 0.0734 (12) | |
H30 | −0.0877 | 0.6046 | 0.1579 | 0.088* | |
C31 | −0.01225 (19) | 0.6966 (3) | 0.2500 (2) | 0.0567 (10) | |
H31 | −0.0432 | 0.7035 | 0.2780 | 0.068* | |
C32 | 0.27833 (17) | 0.4946 (2) | 0.49544 (17) | 0.0316 (7) | |
C33 | 0.3304 (2) | 0.4494 (3) | 0.47003 (19) | 0.0497 (9) | |
H33 | 0.3792 | 0.4803 | 0.4850 | 0.060* | |
C34 | 0.3103 (3) | 0.3584 (3) | 0.4225 (2) | 0.0685 (11) | |
H34 | 0.3462 | 0.3282 | 0.4065 | 0.082* | |
C35 | 0.2391 (3) | 0.3124 (3) | 0.3986 (2) | 0.0631 (11) | |
H35 | 0.2263 | 0.2512 | 0.3665 | 0.076* | |
C36 | 0.1862 (2) | 0.3569 (3) | 0.4223 (2) | 0.0560 (10) | |
H36 | 0.1370 | 0.3266 | 0.4055 | 0.067* | |
C37 | 0.20608 (19) | 0.4469 (2) | 0.47113 (18) | 0.0428 (8) | |
H37 | 0.1703 | 0.4757 | 0.4879 | 0.051* | |
C38 | 0.32903 (16) | 0.4665 (2) | 0.68391 (17) | 0.0308 (7) | |
C39 | 0.40999 (17) | 0.4503 (2) | 0.72235 (18) | 0.0422 (8) | |
C40 | 0.4434 (2) | 0.3588 (3) | 0.7644 (2) | 0.0574 (10) | |
H40 | 0.4975 | 0.3507 | 0.7894 | 0.069* | |
C41 | 0.3961 (2) | 0.2796 (3) | 0.7691 (2) | 0.0600 (10) | |
H41 | 0.4182 | 0.2165 | 0.7959 | 0.072* | |
C42 | 0.3161 (2) | 0.2929 (2) | 0.73429 (19) | 0.0492 (9) | |
H42 | 0.2844 | 0.2393 | 0.7385 | 0.059* | |
C43 | 0.28323 (17) | 0.3853 (2) | 0.69342 (18) | 0.0377 (8) | |
C44 | 0.0106 (3) | 0.5626 (6) | 0.5659 (4) | 0.0985 (15) | |
H44 | 0.0179 | 0.6055 | 0.6107 | 0.118* | |
C45 | 0.0215 (3) | 0.6018 (4) | 0.5019 (5) | 0.0971 (17) | |
H45 | 0.0364 | 0.6722 | 0.5029 | 0.117* | |
C46 | 0.0110 (3) | 0.5397 (6) | 0.4360 (4) | 0.0976 (16) | |
H46 | 0.0187 | 0.5677 | 0.3922 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0335 (5) | 0.0824 (7) | 0.0804 (7) | −0.0091 (5) | 0.0043 (5) | 0.0301 (6) |
Cl2 | 0.0391 (5) | 0.0493 (5) | 0.0719 (6) | −0.0058 (4) | 0.0208 (4) | 0.0117 (5) |
N1 | 0.0479 (17) | 0.0498 (16) | 0.0318 (15) | 0.0014 (14) | 0.0169 (13) | 0.0078 (14) |
N2 | 0.0421 (16) | 0.0338 (14) | 0.0541 (18) | −0.0133 (12) | 0.0222 (14) | −0.0064 (13) |
N3 | 0.0273 (14) | 0.0254 (13) | 0.0274 (14) | 0.0016 (10) | 0.0039 (11) | 0.0000 (11) |
N4 | 0.0342 (15) | 0.0293 (13) | 0.0304 (14) | 0.0001 (11) | 0.0127 (12) | 0.0032 (12) |
O1 | 0.0533 (15) | 0.0415 (13) | 0.0545 (15) | 0.0125 (12) | 0.0228 (12) | 0.0164 (11) |
O2 | 0.0366 (13) | 0.0329 (11) | 0.0334 (13) | −0.0048 (9) | 0.0019 (10) | 0.0026 (9) |
O3 | 0.0338 (12) | 0.0325 (11) | 0.0368 (12) | 0.0063 (9) | 0.0181 (10) | 0.0074 (10) |
C1 | 0.039 (2) | 0.0331 (18) | 0.041 (2) | −0.0036 (15) | 0.0195 (16) | 0.0077 (16) |
C2 | 0.045 (2) | 0.0368 (18) | 0.041 (2) | −0.0055 (15) | 0.0247 (17) | −0.0007 (16) |
C3 | 0.074 (3) | 0.055 (2) | 0.053 (2) | 0.001 (2) | 0.039 (2) | −0.005 (2) |
C4 | 0.076 (3) | 0.053 (2) | 0.077 (3) | 0.004 (2) | 0.053 (2) | −0.009 (2) |
C5 | 0.045 (2) | 0.048 (2) | 0.077 (3) | 0.0125 (17) | 0.033 (2) | 0.009 (2) |
C6 | 0.037 (2) | 0.0432 (19) | 0.049 (2) | −0.0020 (15) | 0.0201 (17) | 0.0018 (17) |
C7 | 0.0309 (17) | 0.0298 (16) | 0.0372 (19) | −0.0049 (13) | 0.0165 (15) | 0.0018 (14) |
C8 | 0.0327 (17) | 0.0286 (16) | 0.0335 (18) | −0.0027 (13) | 0.0137 (14) | 0.0011 (14) |
C9 | 0.050 (2) | 0.0332 (18) | 0.058 (2) | −0.0105 (15) | 0.0176 (18) | −0.0086 (16) |
C10 | 0.0369 (18) | 0.0270 (16) | 0.0312 (18) | 0.0003 (13) | 0.0063 (15) | −0.0032 (14) |
C11 | 0.0285 (17) | 0.0276 (15) | 0.0267 (16) | −0.0004 (13) | 0.0078 (13) | −0.0023 (13) |
C12 | 0.0317 (17) | 0.0265 (15) | 0.0300 (17) | 0.0034 (12) | 0.0123 (14) | 0.0009 (14) |
C13 | 0.0360 (18) | 0.0286 (16) | 0.0328 (18) | −0.0020 (13) | 0.0082 (14) | −0.0016 (14) |
C14 | 0.0285 (16) | 0.0272 (15) | 0.0282 (17) | 0.0001 (12) | 0.0138 (14) | 0.0000 (13) |
C15 | 0.0243 (16) | 0.0330 (16) | 0.0245 (17) | −0.0013 (13) | 0.0101 (14) | −0.0032 (13) |
C16 | 0.0253 (16) | 0.0273 (15) | 0.0321 (17) | −0.0005 (12) | 0.0121 (13) | 0.0004 (14) |
C17 | 0.0251 (16) | 0.0284 (16) | 0.0272 (17) | −0.0040 (13) | 0.0084 (13) | −0.0047 (13) |
C18 | 0.059 (3) | 0.053 (2) | 0.093 (3) | −0.0204 (19) | 0.044 (2) | 0.000 (2) |
C19 | 0.047 (2) | 0.0294 (17) | 0.035 (2) | −0.0028 (15) | 0.0105 (16) | −0.0100 (15) |
C20 | 0.057 (2) | 0.042 (2) | 0.056 (2) | 0.0074 (18) | 0.0152 (19) | −0.0119 (18) |
C21 | 0.054 (3) | 0.059 (3) | 0.094 (4) | 0.009 (2) | 0.017 (3) | −0.033 (3) |
C22 | 0.080 (4) | 0.077 (3) | 0.122 (5) | −0.013 (3) | 0.062 (3) | −0.045 (3) |
C23 | 0.110 (4) | 0.068 (3) | 0.083 (3) | −0.020 (3) | 0.066 (3) | −0.020 (3) |
C24 | 0.076 (3) | 0.042 (2) | 0.052 (3) | −0.0006 (18) | 0.029 (2) | −0.0071 (18) |
C25 | 0.0334 (19) | 0.0423 (19) | 0.044 (2) | 0.0065 (15) | 0.0024 (16) | −0.0003 (16) |
C26 | 0.036 (2) | 0.0308 (17) | 0.0355 (19) | 0.0004 (14) | −0.0021 (16) | 0.0012 (15) |
C27 | 0.050 (2) | 0.060 (2) | 0.043 (2) | −0.0094 (18) | 0.0075 (19) | −0.0028 (19) |
C28 | 0.075 (3) | 0.076 (3) | 0.044 (2) | 0.007 (2) | 0.013 (2) | −0.003 (2) |
C29 | 0.069 (3) | 0.059 (3) | 0.058 (3) | 0.005 (2) | −0.009 (2) | −0.019 (2) |
C30 | 0.044 (2) | 0.052 (2) | 0.084 (3) | −0.0096 (19) | −0.008 (2) | −0.015 (2) |
C31 | 0.037 (2) | 0.046 (2) | 0.065 (2) | −0.0023 (17) | 0.0026 (18) | −0.0054 (19) |
C32 | 0.0392 (19) | 0.0236 (15) | 0.0297 (18) | 0.0067 (13) | 0.0130 (15) | 0.0052 (13) |
C33 | 0.049 (2) | 0.046 (2) | 0.053 (2) | 0.0037 (17) | 0.0219 (18) | −0.0083 (18) |
C34 | 0.082 (3) | 0.056 (2) | 0.069 (3) | 0.017 (2) | 0.033 (2) | −0.019 (2) |
C35 | 0.085 (3) | 0.036 (2) | 0.054 (2) | 0.000 (2) | 0.016 (2) | −0.0161 (18) |
C36 | 0.067 (3) | 0.039 (2) | 0.052 (2) | −0.0141 (18) | 0.017 (2) | −0.0063 (18) |
C37 | 0.050 (2) | 0.0351 (18) | 0.043 (2) | −0.0075 (16) | 0.0203 (17) | −0.0074 (16) |
C38 | 0.0337 (18) | 0.0305 (16) | 0.0265 (17) | 0.0003 (13) | 0.0117 (14) | 0.0031 (13) |
C39 | 0.0315 (19) | 0.051 (2) | 0.039 (2) | 0.0040 (15) | 0.0108 (15) | 0.0102 (17) |
C40 | 0.042 (2) | 0.069 (3) | 0.055 (2) | 0.0199 (19) | 0.0157 (18) | 0.025 (2) |
C41 | 0.068 (3) | 0.047 (2) | 0.061 (3) | 0.022 (2) | 0.025 (2) | 0.0211 (19) |
C42 | 0.059 (2) | 0.0357 (19) | 0.049 (2) | 0.0006 (17) | 0.0207 (18) | 0.0082 (16) |
C43 | 0.0371 (19) | 0.0359 (18) | 0.0381 (19) | 0.0056 (14) | 0.0147 (15) | 0.0040 (15) |
C44 | 0.063 (3) | 0.112 (5) | 0.117 (5) | −0.012 (3) | 0.036 (3) | −0.022 (4) |
C45 | 0.058 (3) | 0.071 (3) | 0.158 (5) | −0.011 (2) | 0.043 (4) | 0.013 (4) |
C46 | 0.064 (3) | 0.126 (5) | 0.103 (5) | −0.001 (3) | 0.038 (3) | 0.031 (4) |
Cl1—C39 | 1.737 (3) | C19—C24 | 1.386 (4) |
Cl2—C43 | 1.725 (3) | C20—C21 | 1.380 (5) |
N1—C1 | 1.365 (4) | C20—H20 | 0.9300 |
N1—C2 | 1.395 (4) | C21—C22 | 1.361 (5) |
N1—H1 | 0.8600 | C21—H21 | 0.9300 |
N2—C9 | 1.449 (4) | C22—C23 | 1.355 (6) |
N2—C18 | 1.463 (4) | C22—H22 | 0.9300 |
N2—C8 | 1.475 (3) | C23—C24 | 1.389 (5) |
N3—C12 | 1.454 (3) | C23—H23 | 0.9300 |
N3—C13 | 1.463 (3) | C24—H24 | 0.9300 |
N3—C25 | 1.463 (3) | C25—C26 | 1.505 (4) |
N4—C17 | 1.280 (3) | C25—H25A | 0.9700 |
N4—O3 | 1.414 (3) | C25—H25B | 0.9700 |
O1—C1 | 1.214 (3) | C26—C27 | 1.371 (5) |
O2—C15 | 1.210 (3) | C26—C31 | 1.383 (4) |
O3—C14 | 1.482 (3) | C27—C28 | 1.381 (5) |
C1—C8 | 1.559 (4) | C27—H27 | 0.9300 |
C2—C3 | 1.371 (4) | C28—C29 | 1.364 (5) |
C2—C7 | 1.391 (4) | C28—H28 | 0.9300 |
C3—C4 | 1.372 (5) | C29—C30 | 1.353 (5) |
C3—H3 | 0.9300 | C29—H29 | 0.9300 |
C4—C5 | 1.379 (5) | C30—C31 | 1.386 (5) |
C4—H4 | 0.9300 | C30—H30 | 0.9300 |
C5—C6 | 1.397 (4) | C31—H31 | 0.9300 |
C5—H5 | 0.9300 | C32—C33 | 1.382 (4) |
C6—C7 | 1.376 (4) | C32—C37 | 1.384 (4) |
C6—H6 | 0.9300 | C33—C34 | 1.381 (5) |
C7—C8 | 1.520 (4) | C33—H33 | 0.9300 |
C8—C11 | 1.585 (4) | C34—C35 | 1.359 (5) |
C9—C10 | 1.513 (4) | C34—H34 | 0.9300 |
C9—H9A | 0.9700 | C35—C36 | 1.371 (5) |
C9—H9B | 0.9700 | C35—H35 | 0.9300 |
C10—C19 | 1.508 (4) | C36—C37 | 1.382 (4) |
C10—C11 | 1.571 (4) | C36—H36 | 0.9300 |
C10—H10 | 0.9800 | C37—H37 | 0.9300 |
C11—C12 | 1.526 (4) | C38—C39 | 1.399 (4) |
C11—C15 | 1.527 (4) | C38—C43 | 1.403 (4) |
C12—H12A | 0.9700 | C39—C40 | 1.373 (4) |
C12—H12B | 0.9700 | C40—C41 | 1.370 (5) |
C13—C14 | 1.512 (4) | C40—H40 | 0.9300 |
C13—H13A | 0.9700 | C41—C42 | 1.379 (5) |
C13—H13B | 0.9700 | C41—H41 | 0.9300 |
C14—C15 | 1.540 (4) | C42—C43 | 1.373 (4) |
C14—C16 | 1.547 (3) | C42—H42 | 0.9300 |
C16—C17 | 1.507 (4) | C44—C46i | 1.349 (7) |
C16—C32 | 1.517 (4) | C44—C45 | 1.349 (6) |
C16—H16 | 0.9800 | C44—H44 | 0.9300 |
C17—C38 | 1.483 (4) | C45—C46 | 1.362 (7) |
C18—H18A | 0.9600 | C45—H45 | 0.9300 |
C18—H18B | 0.9600 | C46—C44i | 1.349 (7) |
C18—H18C | 0.9600 | C46—H46 | 0.9300 |
C19—C20 | 1.385 (4) | ||
C1—N1—C2 | 112.2 (3) | H18A—C18—H18C | 109.5 |
C1—N1—H1 | 123.9 | H18B—C18—H18C | 109.5 |
C2—N1—H1 | 123.9 | C20—C19—C24 | 117.2 (3) |
C9—N2—C18 | 114.0 (2) | C20—C19—C10 | 123.6 (3) |
C9—N2—C8 | 106.9 (2) | C24—C19—C10 | 119.2 (3) |
C18—N2—C8 | 114.9 (2) | C21—C20—C19 | 121.2 (4) |
C12—N3—C13 | 114.5 (2) | C21—C20—H20 | 119.4 |
C12—N3—C25 | 110.6 (2) | C19—C20—H20 | 119.4 |
C13—N3—C25 | 113.3 (2) | C22—C21—C20 | 120.2 (4) |
C17—N4—O3 | 109.5 (2) | C22—C21—H21 | 119.9 |
N4—O3—C14 | 109.06 (18) | C20—C21—H21 | 119.9 |
O1—C1—N1 | 125.6 (3) | C23—C22—C21 | 120.5 (4) |
O1—C1—C8 | 126.7 (3) | C23—C22—H22 | 119.8 |
N1—C1—C8 | 107.4 (3) | C21—C22—H22 | 119.8 |
C3—C2—C7 | 122.2 (3) | C22—C23—C24 | 119.7 (4) |
C3—C2—N1 | 127.8 (3) | C22—C23—H23 | 120.1 |
C7—C2—N1 | 109.9 (3) | C24—C23—H23 | 120.1 |
C2—C3—C4 | 117.9 (3) | C19—C24—C23 | 121.2 (4) |
C2—C3—H3 | 121.1 | C19—C24—H24 | 119.4 |
C4—C3—H3 | 121.1 | C23—C24—H24 | 119.4 |
C3—C4—C5 | 121.4 (3) | N3—C25—C26 | 115.1 (2) |
C3—C4—H4 | 119.3 | N3—C25—H25A | 108.5 |
C5—C4—H4 | 119.3 | C26—C25—H25A | 108.5 |
C4—C5—C6 | 120.3 (3) | N3—C25—H25B | 108.5 |
C4—C5—H5 | 119.9 | C26—C25—H25B | 108.5 |
C6—C5—H5 | 119.9 | H25A—C25—H25B | 107.5 |
C7—C6—C5 | 118.7 (3) | C27—C26—C31 | 118.1 (3) |
C7—C6—H6 | 120.7 | C27—C26—C25 | 122.0 (3) |
C5—C6—H6 | 120.7 | C31—C26—C25 | 119.8 (3) |
C6—C7—C2 | 119.5 (3) | C26—C27—C28 | 121.0 (4) |
C6—C7—C8 | 131.3 (3) | C26—C27—H27 | 119.5 |
C2—C7—C8 | 108.8 (3) | C28—C27—H27 | 119.5 |
N2—C8—C7 | 110.8 (2) | C29—C28—C27 | 120.2 (4) |
N2—C8—C1 | 110.9 (2) | C29—C28—H28 | 119.9 |
C7—C8—C1 | 101.5 (2) | C27—C28—H28 | 119.9 |
N2—C8—C11 | 103.1 (2) | C30—C29—C28 | 119.9 (4) |
C7—C8—C11 | 118.7 (2) | C30—C29—H29 | 120.1 |
C1—C8—C11 | 112.1 (2) | C28—C29—H29 | 120.1 |
N2—C9—C10 | 102.8 (2) | C29—C30—C31 | 120.4 (4) |
N2—C9—H9A | 111.2 | C29—C30—H30 | 119.8 |
C10—C9—H9A | 111.2 | C31—C30—H30 | 119.8 |
N2—C9—H9B | 111.2 | C26—C31—C30 | 120.5 (4) |
C10—C9—H9B | 111.2 | C26—C31—H31 | 119.7 |
H9A—C9—H9B | 109.1 | C30—C31—H31 | 119.7 |
C19—C10—C9 | 116.2 (2) | C33—C32—C37 | 118.1 (3) |
C19—C10—C11 | 116.2 (2) | C33—C32—C16 | 120.1 (3) |
C9—C10—C11 | 103.7 (2) | C37—C32—C16 | 121.6 (3) |
C19—C10—H10 | 106.7 | C34—C33—C32 | 120.3 (3) |
C9—C10—H10 | 106.7 | C34—C33—H33 | 119.9 |
C11—C10—H10 | 106.7 | C32—C33—H33 | 119.9 |
C12—C11—C15 | 106.3 (2) | C35—C34—C33 | 121.2 (4) |
C12—C11—C10 | 113.9 (2) | C35—C34—H34 | 119.4 |
C15—C11—C10 | 111.0 (2) | C33—C34—H34 | 119.4 |
C12—C11—C8 | 112.8 (2) | C34—C35—C36 | 119.4 (3) |
C15—C11—C8 | 108.8 (2) | C34—C35—H35 | 120.3 |
C10—C11—C8 | 104.0 (2) | C36—C35—H35 | 120.3 |
N3—C12—C11 | 110.4 (2) | C35—C36—C37 | 120.0 (3) |
N3—C12—H12A | 109.6 | C35—C36—H36 | 120.0 |
C11—C12—H12A | 109.6 | C37—C36—H36 | 120.0 |
N3—C12—H12B | 109.6 | C36—C37—C32 | 121.0 (3) |
C11—C12—H12B | 109.6 | C36—C37—H37 | 119.5 |
H12A—C12—H12B | 108.1 | C32—C37—H37 | 119.5 |
N3—C13—C14 | 115.4 (2) | C39—C38—C43 | 116.1 (3) |
N3—C13—H13A | 108.4 | C39—C38—C17 | 121.8 (3) |
C14—C13—H13A | 108.4 | C43—C38—C17 | 121.9 (3) |
N3—C13—H13B | 108.4 | C40—C39—C38 | 122.6 (3) |
C14—C13—H13B | 108.4 | C40—C39—Cl1 | 117.6 (3) |
H13A—C13—H13B | 107.5 | C38—C39—Cl1 | 119.8 (2) |
O3—C14—C13 | 108.8 (2) | C41—C40—C39 | 119.2 (3) |
O3—C14—C15 | 99.82 (19) | C41—C40—H40 | 120.4 |
C13—C14—C15 | 115.2 (2) | C39—C40—H40 | 120.4 |
O3—C14—C16 | 104.0 (2) | C40—C41—C42 | 120.5 (3) |
C13—C14—C16 | 115.8 (2) | C40—C41—H41 | 119.8 |
C15—C14—C16 | 111.3 (2) | C42—C41—H41 | 119.8 |
O2—C15—C11 | 123.2 (2) | C43—C42—C41 | 119.9 (3) |
O2—C15—C14 | 119.2 (2) | C43—C42—H42 | 120.1 |
C11—C15—C14 | 117.3 (2) | C41—C42—H42 | 120.1 |
C17—C16—C32 | 109.7 (2) | C42—C43—C38 | 121.6 (3) |
C17—C16—C14 | 100.2 (2) | C42—C43—Cl2 | 117.7 (2) |
C32—C16—C14 | 119.3 (2) | C38—C43—Cl2 | 120.7 (2) |
C17—C16—H16 | 109.0 | C46i—C44—C45 | 119.2 (5) |
C32—C16—H16 | 109.0 | C46i—C44—H44 | 120.4 |
C14—C16—H16 | 109.0 | C45—C44—H44 | 120.4 |
N4—C17—C38 | 120.2 (2) | C44—C45—C46 | 120.9 (5) |
N4—C17—C16 | 114.9 (2) | C44—C45—H45 | 119.6 |
C38—C17—C16 | 124.3 (2) | C46—C45—H45 | 119.6 |
N2—C18—H18A | 109.5 | C44i—C46—C45 | 119.9 (5) |
N2—C18—H18B | 109.5 | C44i—C46—H46 | 120.1 |
H18A—C18—H18B | 109.5 | C45—C46—H46 | 120.1 |
N2—C18—H18C | 109.5 | ||
C17—N4—O3—C14 | −8.7 (3) | C13—C14—C15—O2 | −161.3 (3) |
C2—N1—C1—O1 | 176.4 (3) | C16—C14—C15—O2 | −26.9 (3) |
C2—N1—C1—C8 | 2.4 (3) | O3—C14—C15—C11 | −92.5 (2) |
C1—N1—C2—C3 | −177.9 (3) | C13—C14—C15—C11 | 23.8 (3) |
C1—N1—C2—C7 | −1.1 (3) | C16—C14—C15—C11 | 158.2 (2) |
C7—C2—C3—C4 | 0.0 (5) | O3—C14—C16—C17 | −14.0 (2) |
N1—C2—C3—C4 | 176.4 (3) | C13—C14—C16—C17 | −133.3 (2) |
C2—C3—C4—C5 | −1.4 (5) | C15—C14—C16—C17 | 92.6 (2) |
C3—C4—C5—C6 | 0.6 (5) | O3—C14—C16—C32 | 105.5 (3) |
C4—C5—C6—C7 | 1.5 (5) | C13—C14—C16—C32 | −13.8 (4) |
C5—C6—C7—C2 | −2.8 (4) | C15—C14—C16—C32 | −147.9 (2) |
C5—C6—C7—C8 | −175.4 (3) | O3—N4—C17—C38 | −173.3 (2) |
C3—C2—C7—C6 | 2.1 (4) | O3—N4—C17—C16 | −1.5 (3) |
N1—C2—C7—C6 | −174.9 (3) | C32—C16—C17—N4 | −116.1 (3) |
C3—C2—C7—C8 | 176.3 (3) | C14—C16—C17—N4 | 10.2 (3) |
N1—C2—C7—C8 | −0.7 (3) | C32—C16—C17—C38 | 55.4 (3) |
C9—N2—C8—C7 | −162.9 (2) | C14—C16—C17—C38 | −178.4 (2) |
C18—N2—C8—C7 | 69.4 (3) | C9—C10—C19—C20 | 43.1 (4) |
C9—N2—C8—C1 | 85.1 (3) | C11—C10—C19—C20 | −79.4 (4) |
C18—N2—C8—C1 | −42.5 (3) | C9—C10—C19—C24 | −137.8 (3) |
C9—N2—C8—C11 | −35.0 (3) | C11—C10—C19—C24 | 99.7 (3) |
C18—N2—C8—C11 | −162.6 (2) | C24—C19—C20—C21 | −0.8 (5) |
C6—C7—C8—N2 | 57.4 (4) | C10—C19—C20—C21 | 178.3 (3) |
C2—C7—C8—N2 | −115.9 (3) | C19—C20—C21—C22 | 0.0 (6) |
C6—C7—C8—C1 | 175.2 (3) | C20—C21—C22—C23 | 0.6 (6) |
C2—C7—C8—C1 | 2.0 (3) | C21—C22—C23—C24 | −0.5 (6) |
C6—C7—C8—C11 | −61.5 (4) | C20—C19—C24—C23 | 0.9 (5) |
C2—C7—C8—C11 | 125.3 (3) | C10—C19—C24—C23 | −178.2 (3) |
O1—C1—C8—N2 | −58.8 (4) | C22—C23—C24—C19 | −0.3 (6) |
N1—C1—C8—N2 | 115.1 (3) | C12—N3—C25—C26 | 172.7 (2) |
O1—C1—C8—C7 | −176.5 (3) | C13—N3—C25—C26 | −57.2 (3) |
N1—C1—C8—C7 | −2.6 (3) | N3—C25—C26—C27 | −37.2 (4) |
O1—C1—C8—C11 | 55.8 (4) | N3—C25—C26—C31 | 145.1 (3) |
N1—C1—C8—C11 | −130.3 (2) | C31—C26—C27—C28 | 0.0 (5) |
C18—N2—C9—C10 | 174.3 (3) | C25—C26—C27—C28 | −177.7 (3) |
C8—N2—C9—C10 | 46.2 (3) | C26—C27—C28—C29 | −0.4 (5) |
N2—C9—C10—C19 | −165.7 (2) | C27—C28—C29—C30 | 0.7 (6) |
N2—C9—C10—C11 | −36.9 (3) | C28—C29—C30—C31 | −0.6 (6) |
C19—C10—C11—C12 | 21.3 (3) | C27—C26—C31—C30 | 0.0 (5) |
C9—C10—C11—C12 | −107.5 (3) | C25—C26—C31—C30 | 177.8 (3) |
C19—C10—C11—C15 | −98.7 (3) | C29—C30—C31—C26 | 0.3 (5) |
C9—C10—C11—C15 | 132.5 (2) | C17—C16—C32—C33 | −122.0 (3) |
C19—C10—C11—C8 | 144.5 (2) | C14—C16—C32—C33 | 123.4 (3) |
C9—C10—C11—C8 | 15.7 (3) | C17—C16—C32—C37 | 52.2 (3) |
N2—C8—C11—C12 | 134.5 (2) | C14—C16—C32—C37 | −62.4 (4) |
C7—C8—C11—C12 | −102.8 (3) | C37—C32—C33—C34 | −0.7 (5) |
C1—C8—C11—C12 | 15.1 (3) | C16—C32—C33—C34 | 173.8 (3) |
N2—C8—C11—C15 | −107.8 (2) | C32—C33—C34—C35 | 1.0 (5) |
C7—C8—C11—C15 | 15.0 (3) | C33—C34—C35—C36 | −0.1 (6) |
C1—C8—C11—C15 | 132.9 (2) | C34—C35—C36—C37 | −1.0 (5) |
N2—C8—C11—C10 | 10.5 (3) | C35—C36—C37—C32 | 1.3 (5) |
C7—C8—C11—C10 | 133.3 (2) | C33—C32—C37—C36 | −0.5 (4) |
C1—C8—C11—C10 | −108.8 (2) | C16—C32—C37—C36 | −174.8 (3) |
C13—N3—C12—C11 | 60.1 (3) | N4—C17—C38—C39 | −130.2 (3) |
C25—N3—C12—C11 | −170.5 (2) | C16—C17—C38—C39 | 58.8 (4) |
C15—C11—C12—N3 | −65.3 (3) | N4—C17—C38—C43 | 54.4 (4) |
C10—C11—C12—N3 | 172.1 (2) | C16—C17—C38—C43 | −116.5 (3) |
C8—C11—C12—N3 | 53.8 (3) | C43—C38—C39—C40 | 2.5 (5) |
C12—N3—C13—C14 | −8.7 (3) | C17—C38—C39—C40 | −173.1 (3) |
C25—N3—C13—C14 | −136.8 (3) | C43—C38—C39—Cl1 | −175.4 (2) |
N4—O3—C14—C13 | 138.5 (2) | C17—C38—C39—Cl1 | 8.9 (4) |
N4—O3—C14—C15 | −100.4 (2) | C38—C39—C40—C41 | 0.2 (5) |
N4—O3—C14—C16 | 14.6 (2) | Cl1—C39—C40—C41 | 178.2 (3) |
N3—C13—C14—O3 | 78.7 (3) | C39—C40—C41—C42 | −2.1 (5) |
N3—C13—C14—C15 | −32.4 (3) | C40—C41—C42—C43 | 1.1 (5) |
N3—C13—C14—C16 | −164.7 (2) | C41—C42—C43—C38 | 1.8 (5) |
C12—C11—C15—O2 | −151.9 (3) | C41—C42—C43—Cl2 | −178.8 (3) |
C10—C11—C15—O2 | −27.5 (4) | C39—C38—C43—C42 | −3.4 (4) |
C8—C11—C15—O2 | 86.3 (3) | C17—C38—C43—C42 | 172.2 (3) |
C12—C11—C15—C14 | 22.8 (3) | C39—C38—C43—Cl2 | 177.1 (2) |
C10—C11—C15—C14 | 147.2 (2) | C17—C38—C43—Cl2 | −7.2 (4) |
C8—C11—C15—C14 | −99.0 (3) | C46i—C44—C45—C46 | 0.0 (8) |
O3—C14—C15—O2 | 82.4 (3) | C44—C45—C46—C44i | 0.0 (8) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4ii | 0.86 | 2.25 | 3.017 (3) | 149 |
C6—H6···O2 | 0.93 | 2.48 | 3.083 (4) | 123 |
C10—H10···O2 | 0.98 | 2.34 | 2.850 (3) | 112 |
C12—H12A···O3 | 0.97 | 2.43 | 2.979 (3) | 115 |
C12—H12B···O1 | 0.97 | 2.40 | 2.951 (4) | 116 |
C16—H16···Cl1 | 0.98 | 2.70 | 3.325 (3) | 122 |
C16—H16···O2 | 0.98 | 2.44 | 2.779 (3) | 100 |
C30—H30···O1iii | 0.93 | 2.51 | 3.415 (5) | 166 |
C40—H40···O2iv | 0.93 | 2.48 | 3.381 (5) | 163 |
Symmetry codes: (ii) x, −y+3/2, z−1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C43H36Cl2N4O3·0.5C6H6 |
Mr | 766.71 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 19.005 (7), 12.611 (4), 17.986 (6) |
β (°) | 115.937 (5) |
V (Å3) | 3877 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.38 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.945, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15867, 6770, 3692 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.128, 1.02 |
No. of reflections | 6770 |
No. of parameters | 497 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.27 |
Computer programs: SMART (Bruker,1997), SMART, SAINT (Bruker,1997), SHELXS97 (Sheldrick,1997), SHELXL97 (Sheldrick,1997), SHELXTL (Bruker,1997), SHELXTL.
N2—C8 | 1.475 (3) | C11—C12 | 1.526 (4) |
O3—C14 | 1.482 (3) | C11—C15 | 1.527 (4) |
C1—C8 | 1.559 (4) | C13—C14 | 1.512 (4) |
C7—C8 | 1.520 (4) | C14—C15 | 1.540 (4) |
C8—C11 | 1.585 (4) | C14—C16 | 1.547 (3) |
C10—C11 | 1.571 (4) | ||
N2—C8—C7 | 110.8 (2) | C12—C11—C8 | 112.8 (2) |
N2—C8—C1 | 110.9 (2) | C15—C11—C8 | 108.8 (2) |
C7—C8—C1 | 101.5 (2) | C10—C11—C8 | 104.0 (2) |
N2—C8—C11 | 103.1 (2) | O3—C14—C13 | 108.8 (2) |
C7—C8—C11 | 118.7 (2) | O3—C14—C15 | 99.82 (19) |
C1—C8—C11 | 112.1 (2) | C13—C14—C15 | 115.2 (2) |
C12—C11—C15 | 106.3 (2) | O3—C14—C16 | 104.0 (2) |
C12—C11—C10 | 113.9 (2) | C13—C14—C16 | 115.8 (2) |
C15—C11—C10 | 111.0 (2) | C15—C14—C16 | 111.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 | 2.25 | 3.017 (3) | 149 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
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 for the construction of spiro-compounds (Caramella & Grunanger, 1984). The title compound, (I), was synthesized by a double dipolar cycloaddition. Azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, was first reacted with 1-benzyl-3,5-dibenzylidenepiperidin-4-one. The resulting cycloaddition product was then reacted with 2,6-dichlorobenzonitrile oxide to give (I). The molecular structure of (I) (Fig. 1), revealed the presence of a trispiro ring system, centered about atoms C8, C11 and C14. It consists of a 2-oxindole ring, a pyrrolidine ring, an isoxazoline ring and a piperidone ring.
The bond lengths and angles in (I) are normal within experimental error. Those involving the spiro centers, atoms C8, C11 and C14, are given in Table 1. The pyrrolidine ring (N2/C9/C10/C11/C8) has an envelope conformation with atom C9 displaced by −0.600 (2) Å from the mean plane through atoms N2/C8/C11/C10 [planar to within 0.053 (3) Å]. The dihedral angle between plane N2/C9/C10 and mean plane N2/C8/C11/C10 is 40.9 (4)°. The C19–C24 phenyl ring is inclined to mean plane N2/C8/C11/C10 by 90.4 (3)°.
The 2-oxindole ring (C8/C7/C6/C5/C4/C3/C2/N1/C1) is planar to within 0.018 (3)%A. The dihedral angle between the 2-oxindole ring mean plane and mean plane N2/C8/C11/C10 is 93.1 (3)°.
The isoxazoline ring O3/N4/C17/C16/C14 has an envelope conformation with atom C14 displaced by 0.240 (2) Å from the best plane through atoms O3/N4/C17/C16 [planar to within 0.006 (2) Å]. Phenyl rings C38–C43 and C32–C37 are inclined by 57.9 (4) and 84.9 (2)°, respectively, to mean plane O3/N4/C17/C16.
The piperidone ring has a boat conformation with atoms C12 and C14 displaced by 0.713 (3) and 0.341 (3) Å, respectively, from the best plane through atoms N3/C13/C15/C11.
In the crystal structure, the molecules are linked by an intermolecular N—H···N hydrogen bond, involving atoms N1 and N4 (Table 2 and Fig. 2), so forming a hydrogen-bonded polymer extending in the c direction. A benzene molecule of crystallization, disordered about a center of symmetry, is located between centrosymmetrcally related molecules of (I).