Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059661/bt2616sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059661/bt2616Isup2.hkl |
CCDC reference: 663149
To solution of (1E, 6E)-4-(2-chloro phenylidine)-1, 7-bis (2-cholorophenyl) hepta-1, 6diene- 3, 5dione (1 mmol), isatin (1 mmol) and octa hydro 1H-indole-2-carboxylate and in aqeous methanol (20 ml) was refluxed until the disappearence of starting material as evidenced by TLC. The final product was recrystallized in ethanol and choloroform(2:8)
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
Fig. 1. The molecular configuration and atom numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitory radii. |
C33H30Cl2N2O2 | Z = 8 |
Mr = 557.49 | F(000) = 2336 |
Monoclinic, C2/c | Dx = 1.313 Mg m−3 |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 24.8293 (16) Å | Cell parameters from 10569 reflections |
b = 9.6387 (6) Å | µ = 0.26 mm−1 |
c = 24.0094 (17) Å | T = 293 K |
β = 100.912 (3)° | Block, colourless |
V = 5642.1 (6) Å3 | 0.24 × 0.20 × 0.18 mm |
Bruker APEXII CCD area-detector diffractometer | 8131 independent reflections |
Radiation source: fine-focus sealed tube | 5246 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 29.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −33→34 |
Tmin = 0.939, Tmax = 0.954 | k = −13→13 |
35182 measured reflections | l = −33→30 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0809P)2 + 3.0845P] where P = (Fo2 + 2Fc2)/3 |
8131 reflections | (Δ/σ)max = 0.016 |
472 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
C33H30Cl2N2O2 | V = 5642.1 (6) Å3 |
Mr = 557.49 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.8293 (16) Å | µ = 0.26 mm−1 |
b = 9.6387 (6) Å | T = 293 K |
c = 24.0094 (17) Å | 0.24 × 0.20 × 0.18 mm |
β = 100.912 (3)° |
Bruker APEXII CCD area-detector diffractometer | 8131 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5246 reflections with I > 2σ(I) |
Tmin = 0.939, Tmax = 0.954 | Rint = 0.031 |
35182 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.164 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.65 e Å−3 |
8131 reflections | Δρmin = −0.60 e Å−3 |
472 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 | ||
Cl1 | 0.08524 (3) | 0.95549 (7) | 0.15832 (3) | 0.06593 (18) | |
Cl2 | 0.40447 (3) | 1.11218 (10) | 0.05770 (4) | 0.0987 (3) | |
O1 | 0.22538 (6) | 0.81919 (14) | 0.23356 (6) | 0.0487 (3) | |
O2 | 0.30791 (6) | 0.82469 (18) | 0.06638 (6) | 0.0594 (4) | |
N1 | 0.33152 (6) | 0.96102 (12) | 0.24171 (5) | 0.0296 (3) | |
C2 | 0.31207 (6) | 0.85115 (15) | 0.20058 (6) | 0.0289 (3) | |
C3 | 0.28838 (7) | 0.93942 (16) | 0.14758 (6) | 0.0301 (3) | |
H3 | 0.2558 (7) | 0.9847 (18) | 0.1567 (7) | 0.029 (4)* | |
C4 | 0.33421 (7) | 1.04669 (15) | 0.14776 (7) | 0.0309 (3) | |
H4 | 0.3649 (7) | 1.0012 (19) | 0.1358 (7) | 0.030 (4)* | |
C5 | 0.34852 (7) | 1.08439 (15) | 0.21083 (7) | 0.0313 (3) | |
H5 | 0.3254 (7) | 1.1636 (18) | 0.2160 (7) | 0.028 (4)* | |
C6 | 0.40806 (8) | 1.1131 (2) | 0.23944 (8) | 0.0429 (4) | |
H6A | 0.4345 (8) | 1.054 (2) | 0.2238 (8) | 0.040 (5)* | |
H6B | 0.4189 (9) | 1.213 (2) | 0.2369 (9) | 0.054 (6)* | |
C7 | 0.40712 (8) | 1.06498 (19) | 0.29989 (8) | 0.0401 (4) | |
H7 | 0.3823 (8) | 1.128 (2) | 0.3149 (8) | 0.036 (5)* | |
C8 | 0.45964 (10) | 1.0451 (3) | 0.34284 (10) | 0.0556 (5) | |
H8A | 0.4788 (11) | 1.133 (3) | 0.3502 (12) | 0.075 (8)* | |
H8B | 0.4822 (9) | 0.977 (2) | 0.3284 (9) | 0.054 (6)* | |
C9 | 0.44547 (12) | 0.9898 (3) | 0.39755 (10) | 0.0644 (6) | |
H9A | 0.4801 (13) | 0.973 (3) | 0.4237 (13) | 0.092 (9)* | |
H9B | 0.4235 (12) | 1.061 (3) | 0.4127 (12) | 0.084 (9)* | |
C10 | 0.41086 (13) | 0.8586 (3) | 0.38859 (11) | 0.0681 (7) | |
H10A | 0.4327 (10) | 0.783 (3) | 0.3784 (10) | 0.065 (7)* | |
H10B | 0.4016 (11) | 0.824 (3) | 0.4235 (13) | 0.078 (8)* | |
C11 | 0.35993 (11) | 0.8740 (3) | 0.34230 (9) | 0.0572 (6) | |
H11A | 0.3420 (11) | 0.784 (3) | 0.3330 (11) | 0.070 (7)* | |
H11B | 0.3351 (11) | 0.942 (3) | 0.3543 (11) | 0.075 (8)* | |
C12 | 0.37641 (7) | 0.92858 (17) | 0.28916 (7) | 0.0357 (4) | |
H12 | 0.4018 (8) | 0.861 (2) | 0.2767 (8) | 0.037 (5)* | |
C13 | 0.35180 (7) | 0.73744 (16) | 0.19144 (7) | 0.0329 (3) | |
C14 | 0.40243 (8) | 0.74020 (19) | 0.17579 (9) | 0.0441 (4) | |
H14 | 0.4169 (8) | 0.823 (2) | 0.1667 (9) | 0.046 (5)* | |
C15 | 0.43018 (10) | 0.6167 (2) | 0.17180 (10) | 0.0572 (6) | |
H15 | 0.4648 (11) | 0.619 (2) | 0.1589 (10) | 0.064 (7)* | |
C16 | 0.40719 (11) | 0.4924 (2) | 0.18328 (11) | 0.0636 (7) | |
H16 | 0.4268 (11) | 0.410 (3) | 0.1833 (11) | 0.075 (8)* | |
C17 | 0.35686 (10) | 0.4872 (2) | 0.19983 (10) | 0.0549 (5) | |
H17 | 0.3410 (10) | 0.406 (3) | 0.2082 (11) | 0.067 (7)* | |
C18 | 0.32983 (8) | 0.61061 (16) | 0.20366 (7) | 0.0374 (4) | |
N19 | 0.27867 (7) | 0.63167 (15) | 0.21980 (7) | 0.0405 (4) | |
H19 | 0.2591 (9) | 0.568 (2) | 0.2314 (9) | 0.046 (6)* | |
C20 | 0.26575 (7) | 0.76780 (16) | 0.22028 (7) | 0.0334 (3) | |
C21 | 0.27287 (7) | 0.85917 (18) | 0.09258 (7) | 0.0368 (4) | |
C22 | 0.21529 (8) | 0.8265 (2) | 0.06962 (8) | 0.0427 (4) | |
H22 | 0.2098 (8) | 0.770 (2) | 0.0357 (9) | 0.052 (6)* | |
C23 | 0.17201 (8) | 0.8731 (2) | 0.08916 (8) | 0.0442 (4) | |
H23 | 0.1781 (8) | 0.923 (2) | 0.1225 (10) | 0.050 (6)* | |
C24 | 0.11472 (8) | 0.8535 (2) | 0.06237 (8) | 0.0446 (4) | |
C25 | 0.10014 (10) | 0.8012 (3) | 0.00719 (10) | 0.0582 (6) | |
H25 | 0.1293 (11) | 0.769 (3) | −0.0099 (11) | 0.078 (8)* | |
C26 | 0.04625 (10) | 0.7835 (3) | −0.01841 (11) | 0.0657 (6) | |
H26 | 0.0361 (11) | 0.749 (3) | −0.0580 (12) | 0.076 (8)* | |
C27 | 0.00531 (11) | 0.8181 (3) | 0.00991 (11) | 0.0657 (7) | |
H27 | −0.0299 (13) | 0.807 (3) | −0.0057 (13) | 0.093 (10)* | |
C28 | 0.01747 (9) | 0.8710 (3) | 0.06405 (11) | 0.0587 (6) | |
H28 | −0.0107 (10) | 0.894 (2) | 0.0856 (10) | 0.057 (6)* | |
C29 | 0.07196 (8) | 0.8891 (2) | 0.08982 (9) | 0.0466 (4) | |
C30 | 0.31806 (7) | 1.16913 (17) | 0.10870 (7) | 0.0370 (4) | |
C31 | 0.27304 (10) | 1.2499 (2) | 0.11304 (10) | 0.0568 (6) | |
H31 | 0.2548 (10) | 1.227 (3) | 0.1423 (11) | 0.076 (8)* | |
C32 | 0.25854 (14) | 1.3647 (3) | 0.07904 (13) | 0.0795 (9) | |
H32 | 0.2294 (12) | 1.415 (3) | 0.0855 (12) | 0.080 (9)* | |
C33 | 0.28963 (14) | 1.4019 (3) | 0.04007 (13) | 0.0836 (9) | |
H33 | 0.2787 (14) | 1.478 (4) | 0.0178 (15) | 0.111 (11)* | |
C34 | 0.33413 (13) | 1.3252 (3) | 0.03449 (12) | 0.0757 (8) | |
H34 | 0.3565 (13) | 1.349 (3) | 0.0109 (14) | 0.100 (10)* | |
C35 | 0.34795 (9) | 1.2089 (2) | 0.06815 (9) | 0.0523 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0649 (4) | 0.0765 (4) | 0.0587 (3) | 0.0066 (3) | 0.0176 (3) | −0.0165 (3) |
Cl2 | 0.0773 (5) | 0.1266 (7) | 0.1101 (6) | 0.0276 (4) | 0.0634 (4) | 0.0608 (5) |
O1 | 0.0472 (8) | 0.0453 (7) | 0.0614 (9) | −0.0026 (6) | 0.0300 (7) | 0.0027 (6) |
O2 | 0.0513 (8) | 0.0846 (11) | 0.0458 (8) | −0.0024 (7) | 0.0181 (7) | −0.0272 (7) |
N1 | 0.0393 (7) | 0.0239 (6) | 0.0263 (6) | −0.0026 (5) | 0.0081 (5) | 0.0006 (5) |
C2 | 0.0352 (8) | 0.0245 (7) | 0.0296 (8) | −0.0024 (6) | 0.0123 (6) | −0.0002 (5) |
C3 | 0.0352 (8) | 0.0289 (7) | 0.0278 (8) | −0.0014 (6) | 0.0102 (6) | −0.0005 (6) |
C4 | 0.0381 (9) | 0.0270 (7) | 0.0298 (8) | −0.0008 (6) | 0.0121 (7) | 0.0034 (6) |
C5 | 0.0415 (9) | 0.0214 (7) | 0.0325 (8) | −0.0019 (6) | 0.0110 (7) | 0.0021 (5) |
C6 | 0.0479 (11) | 0.0362 (9) | 0.0440 (10) | −0.0123 (8) | 0.0072 (8) | 0.0020 (7) |
C7 | 0.0455 (10) | 0.0351 (8) | 0.0382 (9) | −0.0029 (7) | 0.0043 (8) | −0.0028 (7) |
C8 | 0.0527 (13) | 0.0540 (12) | 0.0541 (13) | −0.0059 (10) | −0.0051 (10) | −0.0042 (10) |
C9 | 0.0747 (17) | 0.0651 (14) | 0.0440 (12) | 0.0007 (12) | −0.0131 (12) | 0.0005 (10) |
C10 | 0.0857 (19) | 0.0690 (16) | 0.0419 (12) | −0.0066 (14) | −0.0074 (12) | 0.0171 (11) |
C11 | 0.0666 (15) | 0.0648 (14) | 0.0371 (11) | −0.0145 (12) | 0.0024 (10) | 0.0153 (10) |
C12 | 0.0423 (10) | 0.0312 (8) | 0.0323 (8) | −0.0002 (7) | 0.0037 (7) | 0.0014 (6) |
C13 | 0.0425 (9) | 0.0249 (7) | 0.0333 (8) | 0.0010 (6) | 0.0125 (7) | −0.0001 (6) |
C14 | 0.0493 (11) | 0.0319 (9) | 0.0566 (12) | 0.0031 (7) | 0.0244 (9) | 0.0042 (8) |
C15 | 0.0636 (14) | 0.0463 (11) | 0.0713 (15) | 0.0165 (10) | 0.0374 (12) | 0.0082 (10) |
C16 | 0.0875 (17) | 0.0362 (10) | 0.0772 (16) | 0.0214 (11) | 0.0414 (14) | 0.0095 (10) |
C17 | 0.0811 (15) | 0.0266 (9) | 0.0635 (13) | 0.0026 (9) | 0.0305 (12) | 0.0037 (8) |
C18 | 0.0527 (10) | 0.0270 (8) | 0.0346 (9) | −0.0027 (7) | 0.0138 (8) | −0.0004 (6) |
N19 | 0.0509 (9) | 0.0278 (7) | 0.0466 (9) | −0.0101 (6) | 0.0189 (7) | 0.0019 (6) |
C20 | 0.0409 (9) | 0.0311 (8) | 0.0306 (8) | −0.0066 (6) | 0.0126 (7) | −0.0006 (6) |
C21 | 0.0426 (10) | 0.0386 (8) | 0.0306 (8) | −0.0029 (7) | 0.0103 (7) | −0.0031 (6) |
C22 | 0.0482 (11) | 0.0452 (10) | 0.0343 (9) | −0.0074 (8) | 0.0070 (8) | −0.0067 (7) |
C23 | 0.0465 (11) | 0.0517 (11) | 0.0345 (9) | −0.0094 (8) | 0.0083 (8) | −0.0053 (8) |
C24 | 0.0434 (10) | 0.0489 (10) | 0.0410 (10) | −0.0082 (8) | 0.0066 (8) | 0.0012 (8) |
C25 | 0.0507 (13) | 0.0787 (16) | 0.0454 (12) | −0.0132 (11) | 0.0094 (10) | −0.0086 (11) |
C26 | 0.0565 (14) | 0.0903 (18) | 0.0471 (13) | −0.0210 (12) | 0.0015 (11) | −0.0015 (12) |
C27 | 0.0457 (13) | 0.0854 (17) | 0.0610 (15) | −0.0144 (12) | −0.0027 (12) | 0.0109 (13) |
C28 | 0.0433 (12) | 0.0678 (14) | 0.0661 (15) | 0.0004 (10) | 0.0134 (11) | 0.0110 (11) |
C29 | 0.0477 (11) | 0.0452 (10) | 0.0470 (11) | −0.0017 (8) | 0.0097 (9) | 0.0036 (8) |
C30 | 0.0451 (10) | 0.0345 (8) | 0.0319 (8) | −0.0037 (7) | 0.0086 (7) | 0.0055 (6) |
C31 | 0.0698 (15) | 0.0514 (12) | 0.0550 (13) | 0.0172 (10) | 0.0266 (11) | 0.0201 (10) |
C32 | 0.099 (2) | 0.0674 (16) | 0.0767 (18) | 0.0364 (15) | 0.0275 (16) | 0.0332 (13) |
C33 | 0.110 (2) | 0.0707 (17) | 0.0716 (18) | 0.0181 (16) | 0.0212 (16) | 0.0450 (14) |
C34 | 0.088 (2) | 0.0803 (18) | 0.0648 (16) | −0.0002 (15) | 0.0285 (15) | 0.0406 (14) |
C35 | 0.0520 (12) | 0.0597 (12) | 0.0474 (11) | −0.0043 (9) | 0.0148 (9) | 0.0191 (9) |
Cl1—C29 | 1.737 (2) | C13—C18 | 1.392 (2) |
Cl2—C35 | 1.742 (2) | C14—C15 | 1.388 (3) |
O1—C20 | 1.214 (2) | C14—H14 | 0.92 (2) |
O2—C21 | 1.213 (2) | C15—C16 | 1.378 (3) |
N1—C2 | 1.4659 (19) | C15—H15 | 0.97 (3) |
N1—C12 | 1.469 (2) | C16—C17 | 1.382 (3) |
N1—C5 | 1.5035 (19) | C16—H16 | 0.93 (3) |
C2—C13 | 1.518 (2) | C17—C18 | 1.378 (3) |
C2—C20 | 1.549 (2) | C17—H17 | 0.92 (3) |
C2—C3 | 1.551 (2) | C18—N19 | 1.411 (2) |
C3—C21 | 1.516 (2) | N19—C20 | 1.351 (2) |
C3—C4 | 1.537 (2) | N19—H19 | 0.86 (2) |
C3—H3 | 0.980 (18) | C21—C22 | 1.466 (3) |
C4—C30 | 1.514 (2) | C22—C23 | 1.329 (3) |
C4—C5 | 1.532 (2) | C22—H22 | 0.97 (2) |
C4—H4 | 0.968 (18) | C23—C24 | 1.458 (3) |
C5—C6 | 1.533 (3) | C23—H23 | 0.92 (2) |
C5—H5 | 0.977 (18) | C24—C29 | 1.394 (3) |
C6—C7 | 1.528 (3) | C24—C25 | 1.400 (3) |
C6—H6A | 1.00 (2) | C25—C26 | 1.373 (3) |
C6—H6B | 1.00 (2) | C25—H25 | 0.95 (3) |
C7—C8 | 1.514 (3) | C26—C27 | 1.367 (4) |
C7—C12 | 1.517 (2) | C26—H26 | 0.99 (3) |
C7—H7 | 0.978 (19) | C27—C28 | 1.375 (4) |
C8—C9 | 1.519 (4) | C27—H27 | 0.89 (3) |
C8—H8A | 0.97 (3) | C28—C29 | 1.388 (3) |
C8—H8B | 0.97 (2) | C28—H28 | 0.97 (2) |
C9—C10 | 1.522 (4) | C30—C31 | 1.382 (3) |
C9—H9A | 0.98 (3) | C30—C35 | 1.385 (2) |
C9—H9B | 0.99 (3) | C31—C32 | 1.382 (3) |
C10—C11 | 1.525 (3) | C31—H31 | 0.93 (3) |
C10—H10A | 0.96 (3) | C32—C33 | 1.369 (4) |
C10—H10B | 0.97 (3) | C32—H32 | 0.91 (3) |
C11—C12 | 1.507 (3) | C33—C34 | 1.357 (4) |
C11—H11A | 0.98 (3) | C33—H33 | 0.92 (4) |
C11—H11B | 0.98 (3) | C34—C35 | 1.387 (3) |
C12—H12 | 0.993 (19) | C34—H34 | 0.90 (3) |
C13—C14 | 1.379 (2) | C35—Cl2 | 1.742 (2) |
C2—N1—C12 | 118.26 (12) | C14—C13—C2 | 132.56 (14) |
C2—N1—C5 | 109.06 (12) | C18—C13—C2 | 108.19 (14) |
C12—N1—C5 | 107.95 (12) | C13—C14—C15 | 119.51 (18) |
N1—C2—C13 | 118.61 (13) | C13—C14—H14 | 119.9 (13) |
N1—C2—C20 | 109.76 (12) | C15—C14—H14 | 120.6 (13) |
C13—C2—C20 | 102.13 (12) | C16—C15—C14 | 120.2 (2) |
N1—C2—C3 | 100.47 (11) | C16—C15—H15 | 120.6 (14) |
C13—C2—C3 | 115.67 (12) | C14—C15—H15 | 119.1 (14) |
C20—C2—C3 | 110.30 (13) | C15—C16—C17 | 121.36 (19) |
C21—C3—C4 | 114.31 (13) | C15—C16—H16 | 120.5 (17) |
C21—C3—C2 | 115.41 (13) | C17—C16—H16 | 117.9 (17) |
C4—C3—C2 | 101.60 (12) | C18—C17—C16 | 117.80 (19) |
C21—C3—H3 | 109.7 (10) | C18—C17—H17 | 119.4 (16) |
C4—C3—H3 | 110.0 (10) | C16—C17—H17 | 122.8 (16) |
C2—C3—H3 | 105.2 (10) | C17—C18—C13 | 121.94 (18) |
C30—C4—C5 | 114.34 (13) | C17—C18—N19 | 128.15 (16) |
C30—C4—C3 | 114.43 (14) | C13—C18—N19 | 109.91 (14) |
C5—C4—C3 | 101.26 (12) | C20—N19—C18 | 111.69 (14) |
C30—C4—H4 | 107.5 (11) | C20—N19—H19 | 122.8 (14) |
C5—C4—H4 | 110.7 (10) | C18—N19—H19 | 125.3 (14) |
C3—C4—H4 | 108.5 (11) | O1—C20—N19 | 127.43 (15) |
N1—C5—C4 | 105.40 (12) | O1—C20—C2 | 124.52 (14) |
N1—C5—C6 | 104.99 (13) | N19—C20—C2 | 108.05 (14) |
C4—C5—C6 | 120.61 (15) | O2—C21—C22 | 119.38 (16) |
N1—C5—H5 | 109.2 (10) | O2—C21—C3 | 120.18 (16) |
C4—C5—H5 | 106.2 (10) | C22—C21—C3 | 120.41 (15) |
C6—C5—H5 | 110.0 (10) | C23—C22—C21 | 126.20 (17) |
C7—C6—C5 | 100.60 (14) | C23—C22—H22 | 119.5 (12) |
C7—C6—H6A | 108.3 (12) | C21—C22—H22 | 114.2 (12) |
C5—C6—H6A | 112.1 (11) | C22—C23—C24 | 125.92 (18) |
C7—C6—H6B | 113.7 (13) | C22—C23—H23 | 118.3 (13) |
C5—C6—H6B | 113.1 (12) | C24—C23—H23 | 115.8 (13) |
H6A—C6—H6B | 108.8 (17) | C29—C24—C25 | 116.90 (18) |
C8—C7—C12 | 110.28 (16) | C29—C24—C23 | 121.74 (18) |
C8—C7—C6 | 121.29 (18) | C25—C24—C23 | 121.34 (19) |
C12—C7—C6 | 101.50 (14) | C26—C25—C24 | 121.6 (2) |
C8—C7—H7 | 110.4 (11) | C26—C25—H25 | 121.6 (16) |
C12—C7—H7 | 105.5 (11) | C24—C25—H25 | 116.5 (16) |
C6—C7—H7 | 106.6 (11) | C27—C26—C25 | 120.0 (2) |
C7—C8—C9 | 108.8 (2) | C27—C26—H26 | 118.6 (15) |
C7—C8—H8A | 110.0 (16) | C25—C26—H26 | 121.3 (15) |
C9—C8—H8A | 109.6 (17) | C26—C27—C28 | 120.7 (2) |
C7—C8—H8B | 108.9 (14) | C26—C27—H27 | 122 (2) |
C9—C8—H8B | 108.6 (14) | C28—C27—H27 | 118 (2) |
H8A—C8—H8B | 111 (2) | C27—C28—C29 | 119.3 (2) |
C8—C9—C10 | 112.7 (2) | C27—C28—H28 | 122.5 (14) |
C8—C9—H9A | 107.0 (18) | C29—C28—H28 | 118.2 (14) |
C10—C9—H9A | 111.1 (18) | C28—C29—C24 | 121.6 (2) |
C8—C9—H9B | 108.0 (17) | C28—C29—Cl1 | 117.56 (17) |
C10—C9—H9B | 107.1 (17) | C24—C29—Cl1 | 120.87 (15) |
H9A—C9—H9B | 111 (2) | C31—C30—C35 | 116.47 (17) |
C9—C10—C11 | 113.0 (2) | C31—C30—C4 | 121.03 (16) |
C9—C10—H10A | 109.3 (16) | C35—C30—C4 | 122.47 (17) |
C11—C10—H10A | 108.5 (15) | C32—C31—C30 | 122.0 (2) |
C9—C10—H10B | 112.7 (17) | C32—C31—H31 | 121.6 (17) |
C11—C10—H10B | 111.4 (16) | C30—C31—H31 | 116.2 (16) |
H10A—C10—H10B | 101 (2) | C33—C32—C31 | 119.7 (3) |
C12—C11—C10 | 109.3 (2) | C33—C32—H32 | 123.2 (19) |
C12—C11—H11A | 107.4 (15) | C31—C32—H32 | 117.0 (19) |
C10—C11—H11A | 111.0 (15) | C34—C33—C32 | 120.0 (2) |
C12—C11—H11B | 107.6 (16) | C34—C33—H33 | 122 (2) |
C10—C11—H11B | 109.4 (16) | C32—C33—H33 | 118 (2) |
H11A—C11—H11B | 112 (2) | C33—C34—C35 | 119.9 (2) |
N1—C12—C11 | 116.32 (16) | C33—C34—H34 | 122 (2) |
N1—C12—C7 | 103.32 (13) | C35—C34—H34 | 118 (2) |
C11—C12—C7 | 111.52 (16) | C30—C35—C34 | 121.8 (2) |
N1—C12—H12 | 109.7 (11) | C30—C35—Cl2 | 120.44 (15) |
C11—C12—H12 | 108.4 (11) | C34—C35—Cl2 | 117.75 (18) |
C7—C12—H12 | 107.1 (11) | C30—C35—Cl2 | 120.44 (15) |
C14—C13—C18 | 119.22 (15) | C34—C35—Cl2 | 117.75 (18) |
C12—N1—C2—C13 | −27.37 (19) | C16—C17—C18—N19 | −179.6 (2) |
C5—N1—C2—C13 | 96.41 (15) | C14—C13—C18—C17 | −0.9 (3) |
C12—N1—C2—C20 | 89.38 (16) | C2—C13—C18—C17 | −179.32 (18) |
C5—N1—C2—C20 | −146.84 (13) | C14—C13—C18—N19 | 178.74 (16) |
C12—N1—C2—C3 | −154.43 (13) | C2—C13—C18—N19 | 0.34 (19) |
C5—N1—C2—C3 | −30.65 (15) | C17—C18—N19—C20 | 178.2 (2) |
N1—C2—C3—C21 | 169.87 (13) | C13—C18—N19—C20 | −1.4 (2) |
C13—C2—C3—C21 | 40.89 (19) | C18—N19—C20—O1 | −178.11 (17) |
C20—C2—C3—C21 | −74.35 (17) | C18—N19—C20—C2 | 1.9 (2) |
N1—C2—C3—C4 | 45.62 (14) | N1—C2—C20—O1 | 51.7 (2) |
C13—C2—C3—C4 | −83.36 (15) | C13—C2—C20—O1 | 178.44 (17) |
C20—C2—C3—C4 | 161.40 (12) | C3—C2—C20—O1 | −58.1 (2) |
C21—C3—C4—C30 | 68.36 (18) | N1—C2—C20—N19 | −128.25 (14) |
C2—C3—C4—C30 | −166.65 (13) | C13—C2—C20—N19 | −1.55 (17) |
C21—C3—C4—C5 | −168.14 (14) | C3—C2—C20—N19 | 121.95 (15) |
C2—C3—C4—C5 | −43.14 (14) | C4—C3—C21—O2 | 37.5 (2) |
C2—N1—C5—C4 | 4.06 (16) | C2—C3—C21—O2 | −79.8 (2) |
C12—N1—C5—C4 | 133.74 (13) | C4—C3—C21—C22 | −140.45 (16) |
C2—N1—C5—C6 | −124.30 (14) | C2—C3—C21—C22 | 102.23 (18) |
C12—N1—C5—C6 | 5.38 (17) | O2—C21—C22—C23 | −170.3 (2) |
C30—C4—C5—N1 | 148.21 (14) | C3—C21—C22—C23 | 7.7 (3) |
C3—C4—C5—N1 | 24.64 (15) | C21—C22—C23—C24 | 172.42 (18) |
C30—C4—C5—C6 | −93.44 (18) | C22—C23—C24—C29 | 170.9 (2) |
C3—C4—C5—C6 | 142.99 (15) | C22—C23—C24—C25 | −10.8 (3) |
N1—C5—C6—C7 | −31.18 (17) | C29—C24—C25—C26 | −1.1 (3) |
C4—C5—C6—C7 | −149.73 (15) | C23—C24—C25—C26 | −179.5 (2) |
C5—C6—C7—C8 | 167.58 (17) | C24—C25—C26—C27 | 0.4 (4) |
C5—C6—C7—C12 | 45.07 (17) | C25—C26—C27—C28 | 0.1 (4) |
C12—C7—C8—C9 | −58.8 (2) | C26—C27—C28—C29 | 0.1 (4) |
C6—C7—C8—C9 | −177.02 (19) | C27—C28—C29—C24 | −0.8 (3) |
C7—C8—C9—C10 | 54.5 (3) | C27—C28—C29—Cl1 | −179.73 (19) |
C8—C9—C10—C11 | −52.3 (4) | C25—C24—C29—C28 | 1.2 (3) |
C9—C10—C11—C12 | 51.9 (3) | C23—C24—C29—C28 | 179.63 (19) |
C2—N1—C12—C11 | −90.1 (2) | C25—C24—C29—Cl1 | −179.81 (17) |
C5—N1—C12—C11 | 145.60 (17) | C23—C24—C29—Cl1 | −1.4 (3) |
C2—N1—C12—C7 | 147.41 (14) | C5—C4—C30—C31 | −60.8 (2) |
C5—N1—C12—C7 | 23.08 (17) | C3—C4—C30—C31 | 55.4 (2) |
C10—C11—C12—N1 | −174.89 (18) | C5—C4—C30—C35 | 117.3 (2) |
C10—C11—C12—C7 | −56.8 (3) | C3—C4—C30—C35 | −126.51 (19) |
C8—C7—C12—N1 | −172.44 (16) | C35—C30—C31—C32 | −0.3 (4) |
C6—C7—C12—N1 | −42.64 (18) | C4—C30—C31—C32 | 177.9 (2) |
C8—C7—C12—C11 | 61.9 (2) | C30—C31—C32—C33 | −0.7 (5) |
C6—C7—C12—C11 | −168.31 (18) | C31—C32—C33—C34 | 0.7 (5) |
N1—C2—C13—C14 | −56.7 (3) | C32—C33—C34—C35 | 0.3 (5) |
C20—C2—C13—C14 | −177.40 (19) | C31—C30—C35—C34 | 1.3 (3) |
C3—C2—C13—C14 | 62.8 (3) | C4—C30—C35—C34 | −176.9 (2) |
N1—C2—C13—C18 | 121.44 (15) | C31—C30—C35—Cl2 | −178.35 (18) |
C20—C2—C13—C18 | 0.70 (17) | C4—C30—C35—Cl2 | 3.4 (3) |
C3—C2—C13—C18 | −119.10 (15) | C31—C30—C35—Cl2 | −178.35 (18) |
C18—C13—C14—C15 | 0.8 (3) | C4—C30—C35—Cl2 | 3.4 (3) |
C2—C13—C14—C15 | 178.76 (19) | C33—C34—C35—C30 | −1.3 (4) |
C13—C14—C15—C16 | 0.2 (4) | C33—C34—C35—Cl2 | 178.4 (3) |
C14—C15—C16—C17 | −1.1 (4) | C33—C34—C35—Cl2 | 178.4 (3) |
C15—C16—C17—C18 | 1.0 (4) | Cl2—Cl2—C35—C30 | 0.00 (4) |
C16—C17—C18—C13 | 0.0 (3) | Cl2—Cl2—C35—C34 | 0.00 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl2 | 0.968 (18) | 2.515 (18) | 3.0895 (16) | 118.0 (13) |
N19—H19···O1i | 0.86 (2) | 2.54 (2) | 3.222 (2) | 136.0 (18) |
C17—H17···O1i | 0.92 (3) | 2.50 (3) | 3.253 (3) | 140 (2) |
C22—H22···O2ii | 0.97 (2) | 2.57 (2) | 3.522 (2) | 166.3 (17) |
C25—H25···O2ii | 0.95 (3) | 2.43 (3) | 3.366 (3) | 171 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+3/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C33H30Cl2N2O2 |
Mr | 557.49 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.8293 (16), 9.6387 (6), 24.0094 (17) |
β (°) | 100.912 (3) |
V (Å3) | 5642.1 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.24 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.939, 0.954 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35182, 8131, 5246 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.701 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.164, 1.02 |
No. of reflections | 8131 |
No. of parameters | 472 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.65, −0.60 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···Cl2 | 0.968 (18) | 2.515 (18) | 3.0895 (16) | 118.0 (13) |
N19—H19···O1i | 0.86 (2) | 2.54 (2) | 3.222 (2) | 136.0 (18) |
C17—H17···O1i | 0.92 (3) | 2.50 (3) | 3.253 (3) | 140 (2) |
C22—H22···O2ii | 0.97 (2) | 2.57 (2) | 3.522 (2) | 166.3 (17) |
C25—H25···O2ii | 0.95 (3) | 2.43 (3) | 3.366 (3) | 171 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+3/2, −z. |
Oxindole derivatives are found to be potent aldose reductase inhibitors (ARIs), which help to treat and prevent diabetic complications arising from elevated levels of sorbitol (Rajeswaran et al., 1999). Pyrrolidine derivatives are present in a large number of biologically active natural products and numerous therapeutic agents. Radical cyclizations have emerged as a useful synthetic tool and have been reported in the synthesis of alkaloids and related pyrrolidinic compounds via the generation and trapping of nitrogen-centred radicals e.g. aminyl, iminyl, amidyl radicals etc. (Esker & Newcomb, 1993; Fallis & Brinza, 1997; Bowman et al., 1996; Guindon et al., 2001).
The bond lengths in the indolizidine moiety are slightly longer than the values reported for similar structures (Seshadri et al., 2003; Jeyabharathi et al., 2001). This may be due to steric forces caused by the bulky substituents on the indolizidine moiety. The sum of angle at N1 of the indolizidine ring (335.3°) is in accordance with sp3 hybridization (Beddoes et al., 1986), and the sum of angles at N19 of the oxindole moiety (359.8°) is in accordance with sp2 hybridization.
Both the five-membered rings of the indolizidine moiety adopt envelope conformations, with the the puckering parameters q2 and ϕ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters, Δ, (Nardelli et al., 1983) as follows: for ring A are q2=0.463 (2) Å, ϕ=68.4 (2)°, and Δs(C3)=4.6 (2); for ring B are q2=0.454 (2) Å,ϕ=280.8 (2)°, Δs()=6.0 (2). Oxindole ring systems are essentially planar, with atoms O1 displaced by 0.067 (1) Å.
The molecule is stabilized by intra molecular C—H···Cl interactions and the crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds. The molecule at (x, y, z) and (1/2 - x, 3/2 - y, z) are linked by C22—H22···O2 hydrogen bonds into centrosymmetric R22(8) dimers. Atom C25 of the molecule at (x, y, z) donate one proton to atom O2 molecule at (1/2 - x, 3/2 - y, z), forming a R22(14) dimers. These two dimers R22(8) and R22(14) are cross-linked along [0 1 0] direction through C—H···O and N—H···O intermolecular hydrogen bonds.