Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013964/ci6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013964/ci6054Isup2.hkl |
CCDC reference: 172228
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.141
- Data-to-parameter ratio = 13.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A mixture of 2,6-dibenzylidenecyclohexanone (1 mmol), sarcosine (1 mmol) and isotin (1 mmol) in methanol was refluxed for 4 h. After the reaction, the solvent was evaporated in vacuo and the resulting crude product was purified by column chromatography using a hexane–ethyl acetate mixture (9:1). Slow evaporation of the isolated compound from ethanol solution gave light-yellow single crystals suitable for X-ray structure determination.
After checking their presence in the difference map, all H atoms were fixed geometrically and allowed to ride on the parent C atoms and refined isotropically. Due to large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C30H28N2O2 | Z = 4 |
Mr = 448.54 | F(000) = 952 |
Triclinic, P1 | Dx = 1.249 Mg m−3 |
a = 12.3624 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.0640 (2) Å | Cell parameters from 6647 reflections |
c = 17.1439 (3) Å | θ = 1.3–29.5° |
α = 110.066 (1)° | µ = 0.08 mm−1 |
β = 93.200 (1)° | T = 293 K |
γ = 110.534 (1)° | Slab, light yellow |
V = 2386.13 (6) Å3 | 0.36 × 0.24 × 0.16 mm |
Siemens SMART CCD area-detector diffractometer | 8228 independent reflections |
Radiation source: fine-focus sealed tube | 4402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.3° |
ω scans | h = −14→14 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −15→9 |
Tmin = 0.972, Tmax = 0.988 | l = −20→20 |
13509 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max < 0.001 |
8228 reflections | Δρmax = 0.23 e Å−3 |
616 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (1) |
C30H28N2O2 | γ = 110.534 (1)° |
Mr = 448.54 | V = 2386.13 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.3624 (1) Å | Mo Kα radiation |
b = 13.0640 (2) Å | µ = 0.08 mm−1 |
c = 17.1439 (3) Å | T = 293 K |
α = 110.066 (1)° | 0.36 × 0.24 × 0.16 mm |
β = 93.200 (1)° |
Siemens SMART CCD area-detector diffractometer | 8228 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 4402 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.988 | Rint = 0.064 |
13509 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.23 e Å−3 |
8228 reflections | Δρmin = −0.26 e Å−3 |
616 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
O1A | 0.02652 (14) | 0.41605 (15) | 0.06499 (11) | 0.0461 (5) | |
O2A | 0.32236 (16) | 0.21054 (17) | 0.08694 (12) | 0.0547 (5) | |
N1A | 0.08413 (17) | 0.23158 (18) | 0.10979 (13) | 0.0398 (5) | |
N2A | 0.37296 (18) | 0.35678 (19) | 0.21900 (14) | 0.0442 (6) | |
H2AA | 0.4382 | 0.3536 | 0.2357 | 0.053* | |
C1A | 0.3044 (2) | 0.2888 (2) | 0.14034 (17) | 0.0401 (6) | |
C2A | 0.3252 (2) | 0.4322 (2) | 0.26958 (16) | 0.0378 (6) | |
C3A | 0.3661 (2) | 0.5065 (2) | 0.35383 (17) | 0.0484 (7) | |
H3AA | 0.4355 | 0.5145 | 0.3839 | 0.058* | |
C4A | 0.3006 (2) | 0.5689 (3) | 0.39223 (18) | 0.0545 (8) | |
H4AA | 0.3260 | 0.6193 | 0.4492 | 0.065* | |
C5A | 0.1982 (2) | 0.5576 (2) | 0.34740 (17) | 0.0520 (7) | |
H5AA | 0.1559 | 0.6010 | 0.3743 | 0.062* | |
C6A | 0.1574 (2) | 0.4822 (2) | 0.26270 (16) | 0.0432 (7) | |
H6AA | 0.0869 | 0.4733 | 0.2334 | 0.052* | |
C7A | 0.2226 (2) | 0.4204 (2) | 0.22224 (15) | 0.0354 (6) | |
C8A | 0.1997 (2) | 0.3288 (2) | 0.13273 (15) | 0.0358 (6) | |
C9A | 0.1964 (2) | 0.3686 (2) | 0.05471 (15) | 0.0342 (6) | |
C10A | 0.1344 (2) | 0.4552 (2) | 0.07441 (15) | 0.0364 (6) | |
C11A | 0.2018 (2) | 0.5859 (2) | 0.10707 (16) | 0.0382 (6) | |
C12A | 0.1464 (2) | 0.6528 (2) | 0.14777 (17) | 0.0461 (7) | |
H12A | 0.0716 | 0.6123 | 0.1550 | 0.055* | |
C13A | 0.1891 (2) | 0.7826 (2) | 0.18259 (18) | 0.0439 (7) | |
C14A | 0.1755 (3) | 0.8422 (3) | 0.2631 (2) | 0.0660 (9) | |
H14A | 0.1423 | 0.8003 | 0.2959 | 0.079* | |
C15A | 0.2114 (3) | 0.9641 (3) | 0.2946 (2) | 0.0829 (11) | |
H15A | 0.2049 | 1.0038 | 0.3496 | 0.100* | |
C16A | 0.2562 (3) | 1.0274 (3) | 0.2465 (3) | 0.0780 (11) | |
H16A | 0.2791 | 1.1092 | 0.2682 | 0.094* | |
C17A | 0.2668 (3) | 0.9693 (3) | 0.1668 (2) | 0.0691 (9) | |
H17A | 0.2966 | 1.0115 | 0.1334 | 0.083* | |
C18A | 0.2339 (2) | 0.8490 (3) | 0.1353 (2) | 0.0572 (8) | |
H18A | 0.2420 | 0.8108 | 0.0805 | 0.069* | |
C19A | 0.3276 (2) | 0.6338 (2) | 0.09533 (18) | 0.0468 (7) | |
H19A | 0.3703 | 0.7121 | 0.1393 | 0.056* | |
H19B | 0.3277 | 0.6413 | 0.0410 | 0.056* | |
C20A | 0.3896 (2) | 0.5531 (2) | 0.09918 (17) | 0.0460 (7) | |
H20A | 0.4674 | 0.5821 | 0.0865 | 0.055* | |
H20B | 0.3989 | 0.5535 | 0.1559 | 0.055* | |
C21A | 0.3182 (2) | 0.4273 (2) | 0.03562 (16) | 0.0415 (6) | |
H21A | 0.3629 | 0.3791 | 0.0348 | 0.050* | |
H21B | 0.3071 | 0.4287 | −0.0204 | 0.050* | |
C22A | 0.0673 (2) | 0.1593 (2) | 0.01987 (16) | 0.0459 (7) | |
H22A | −0.0153 | 0.1087 | −0.0040 | 0.055* | |
H22B | 0.1124 | 0.1102 | 0.0116 | 0.055* | |
C23A | 0.1123 (2) | 0.2505 (2) | −0.02084 (15) | 0.0391 (6) | |
H23A | 0.0439 | 0.2651 | −0.0377 | 0.047* | |
C24A | 0.1572 (2) | 0.2070 (2) | −0.10116 (16) | 0.0418 (6) | |
C25A | 0.2342 (3) | 0.1518 (3) | −0.1091 (2) | 0.0780 (11) | |
H25A | 0.2631 | 0.1410 | −0.0626 | 0.094* | |
C26A | 0.2701 (3) | 0.1117 (4) | −0.1849 (2) | 0.0933 (13) | |
H26A | 0.3240 | 0.0762 | −0.1882 | 0.112* | |
C27A | 0.2271 (3) | 0.1236 (3) | −0.2545 (2) | 0.0699 (9) | |
H27A | 0.2498 | 0.0949 | −0.3057 | 0.084* | |
C28A | 0.1515 (3) | 0.1773 (3) | −0.2486 (2) | 0.0677 (9) | |
H28A | 0.1226 | 0.1866 | −0.2958 | 0.081* | |
C29A | 0.1158 (3) | 0.2193 (3) | −0.17249 (18) | 0.0566 (8) | |
H29A | 0.0632 | 0.2562 | −0.1697 | 0.068* | |
C30A | 0.0628 (2) | 0.1629 (2) | 0.16399 (18) | 0.0577 (8) | |
H30A | −0.0153 | 0.1018 | 0.1441 | 0.087* | |
H30B | 0.0703 | 0.2147 | 0.2213 | 0.087* | |
H30C | 0.1194 | 0.1277 | 0.1619 | 0.087* | |
O1B | 0.45692 (15) | 0.68176 (16) | −0.35926 (12) | 0.0550 (5) | |
O2B | 0.09725 (16) | 0.47035 (19) | −0.23569 (13) | 0.0621 (6) | |
N1B | 0.36504 (17) | 0.57416 (19) | −0.22434 (13) | 0.0403 (5) | |
N2B | 0.15068 (19) | 0.6668 (2) | −0.15352 (15) | 0.0578 (7) | |
H2BA | 0.0910 | 0.6599 | −0.1292 | 0.069* | |
C1B | 0.1634 (2) | 0.5749 (3) | −0.21241 (18) | 0.0472 (7) | |
C2B | 0.2448 (2) | 0.7747 (3) | −0.13596 (17) | 0.0469 (7) | |
C3B | 0.2640 (3) | 0.8842 (3) | −0.07577 (18) | 0.0590 (8) | |
H3BA | 0.2087 | 0.8949 | −0.0427 | 0.071* | |
C4B | 0.3676 (3) | 0.9776 (3) | −0.06591 (18) | 0.0607 (8) | |
H4BA | 0.3824 | 1.0526 | −0.0258 | 0.073* | |
C5B | 0.4495 (3) | 0.9614 (3) | −0.11463 (18) | 0.0560 (8) | |
H5BA | 0.5192 | 1.0255 | −0.1069 | 0.067* | |
C6B | 0.4291 (2) | 0.8499 (2) | −0.17558 (17) | 0.0457 (7) | |
H6BA | 0.4851 | 0.8394 | −0.2081 | 0.055* | |
C7B | 0.3258 (2) | 0.7556 (2) | −0.18725 (16) | 0.0398 (6) | |
C8B | 0.2817 (2) | 0.6244 (2) | −0.24240 (16) | 0.0372 (6) | |
C9B | 0.2616 (2) | 0.5809 (2) | −0.34267 (15) | 0.0359 (6) | |
C10B | 0.3567 (2) | 0.6788 (2) | −0.36207 (15) | 0.0377 (6) | |
C11B | 0.3277 (2) | 0.7701 (2) | −0.38115 (15) | 0.0394 (6) | |
C12B | 0.4188 (2) | 0.8669 (2) | −0.37696 (17) | 0.0486 (7) | |
H12B | 0.4930 | 0.8680 | −0.3627 | 0.058* | |
C13B | 0.4189 (2) | 0.9712 (3) | −0.39142 (18) | 0.0496 (7) | |
C14B | 0.5052 (3) | 1.0820 (3) | −0.3403 (2) | 0.0659 (9) | |
H14B | 0.5603 | 1.0876 | −0.2982 | 0.079* | |
C15B | 0.5104 (3) | 1.1826 (3) | −0.3510 (2) | 0.0809 (11) | |
H15B | 0.5683 | 1.2557 | −0.3158 | 0.097* | |
C16B | 0.4308 (4) | 1.1766 (3) | −0.4131 (2) | 0.0800 (11) | |
H16B | 0.4343 | 1.2452 | −0.4199 | 0.096* | |
C17B | 0.3464 (4) | 1.0689 (4) | −0.4648 (2) | 0.0860 (12) | |
H17B | 0.2922 | 1.0641 | −0.5072 | 0.103* | |
C18B | 0.3409 (3) | 0.9663 (3) | −0.4544 (2) | 0.0726 (10) | |
H18B | 0.2837 | 0.8934 | −0.4905 | 0.087* | |
C19B | 0.2002 (2) | 0.7536 (2) | −0.40103 (18) | 0.0517 (7) | |
H19C | 0.1736 | 0.7201 | −0.4621 | 0.062* | |
H19D | 0.1954 | 0.8305 | −0.3790 | 0.062* | |
C20B | 0.1183 (2) | 0.6735 (2) | −0.36403 (18) | 0.0488 (7) | |
H20C | 0.1323 | 0.7144 | −0.3030 | 0.059* | |
H20D | 0.0370 | 0.6545 | −0.3871 | 0.059* | |
C21B | 0.1391 (2) | 0.5605 (2) | −0.38484 (17) | 0.0442 (7) | |
H21C | 0.1295 | 0.5228 | −0.4458 | 0.053* | |
H21D | 0.0798 | 0.5067 | −0.3668 | 0.053* | |
C22B | 0.3241 (2) | 0.4534 (2) | −0.28920 (17) | 0.0485 (7) | |
H22C | 0.2565 | 0.3997 | −0.2772 | 0.058* | |
H22D | 0.3863 | 0.4238 | −0.2927 | 0.058* | |
C23B | 0.2908 (2) | 0.4673 (2) | −0.37090 (16) | 0.0428 (7) | |
H23B | 0.3629 | 0.4872 | −0.3937 | 0.051* | |
C24B | 0.2004 (3) | 0.3555 (2) | −0.43926 (19) | 0.0546 (8) | |
C25B | 0.0983 (3) | 0.2829 (3) | −0.4228 (2) | 0.0764 (10) | |
H25B | 0.0828 | 0.3038 | −0.3683 | 0.092* | |
C26B | 0.0200 (4) | 0.1796 (3) | −0.4878 (4) | 0.1114 (17) | |
H26B | −0.0478 | 0.1322 | −0.4762 | 0.134* | |
C27B | 0.0404 (6) | 0.1467 (4) | −0.5677 (4) | 0.132 (3) | |
H27B | −0.0115 | 0.0761 | −0.6102 | 0.159* | |
C28B | 0.1381 (5) | 0.2182 (4) | −0.5849 (3) | 0.1121 (18) | |
H28B | 0.1507 | 0.1984 | −0.6401 | 0.134* | |
C29B | 0.2184 (4) | 0.3200 (3) | −0.5210 (2) | 0.0799 (11) | |
H29B | 0.2863 | 0.3656 | −0.5336 | 0.096* | |
C30B | 0.3810 (2) | 0.5784 (3) | −0.13740 (17) | 0.0584 (8) | |
H30D | 0.4101 | 0.6594 | −0.0978 | 0.088* | |
H30E | 0.4365 | 0.5446 | −0.1304 | 0.088* | |
H30F | 0.3067 | 0.5342 | −0.1273 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0357 (10) | 0.0480 (11) | 0.0594 (13) | 0.0192 (9) | 0.0180 (9) | 0.0222 (10) |
O2A | 0.0665 (13) | 0.0529 (12) | 0.0523 (13) | 0.0386 (11) | 0.0132 (10) | 0.0134 (10) |
N1A | 0.0393 (12) | 0.0354 (12) | 0.0387 (13) | 0.0076 (10) | 0.0085 (10) | 0.0146 (11) |
N2A | 0.0376 (12) | 0.0519 (14) | 0.0451 (15) | 0.0227 (11) | 0.0038 (11) | 0.0167 (12) |
C1A | 0.0426 (15) | 0.0395 (16) | 0.0433 (18) | 0.0186 (13) | 0.0138 (13) | 0.0187 (14) |
C2A | 0.0349 (14) | 0.0377 (15) | 0.0400 (16) | 0.0116 (12) | 0.0094 (12) | 0.0167 (13) |
C3A | 0.0418 (15) | 0.0555 (18) | 0.0401 (18) | 0.0135 (14) | 0.0038 (13) | 0.0160 (15) |
C4A | 0.0544 (18) | 0.061 (2) | 0.0346 (17) | 0.0168 (16) | 0.0090 (14) | 0.0096 (15) |
C5A | 0.0518 (17) | 0.0585 (19) | 0.0444 (19) | 0.0256 (15) | 0.0190 (15) | 0.0129 (15) |
C6A | 0.0374 (14) | 0.0483 (17) | 0.0390 (17) | 0.0161 (13) | 0.0109 (12) | 0.0114 (14) |
C7A | 0.0369 (14) | 0.0349 (15) | 0.0352 (15) | 0.0128 (12) | 0.0092 (12) | 0.0157 (12) |
C8A | 0.0360 (14) | 0.0328 (14) | 0.0390 (16) | 0.0152 (12) | 0.0068 (12) | 0.0129 (12) |
C9A | 0.0340 (13) | 0.0345 (14) | 0.0378 (15) | 0.0145 (12) | 0.0107 (11) | 0.0168 (12) |
C10A | 0.0347 (15) | 0.0423 (16) | 0.0376 (16) | 0.0156 (13) | 0.0136 (12) | 0.0202 (13) |
C11A | 0.0351 (14) | 0.0397 (15) | 0.0456 (17) | 0.0161 (13) | 0.0127 (12) | 0.0213 (13) |
C12A | 0.0394 (15) | 0.0458 (17) | 0.060 (2) | 0.0211 (14) | 0.0188 (14) | 0.0231 (15) |
C13A | 0.0389 (15) | 0.0416 (16) | 0.0579 (19) | 0.0227 (13) | 0.0132 (13) | 0.0192 (15) |
C14A | 0.087 (2) | 0.064 (2) | 0.058 (2) | 0.047 (2) | 0.0175 (18) | 0.0187 (18) |
C15A | 0.114 (3) | 0.070 (3) | 0.060 (2) | 0.057 (2) | 0.003 (2) | 0.000 (2) |
C16A | 0.073 (2) | 0.046 (2) | 0.104 (3) | 0.0297 (19) | −0.004 (2) | 0.013 (2) |
C17A | 0.064 (2) | 0.050 (2) | 0.102 (3) | 0.0253 (18) | 0.024 (2) | 0.035 (2) |
C18A | 0.0587 (18) | 0.0441 (19) | 0.078 (2) | 0.0270 (15) | 0.0259 (16) | 0.0247 (17) |
C19A | 0.0403 (15) | 0.0425 (16) | 0.0585 (19) | 0.0136 (13) | 0.0200 (13) | 0.0221 (14) |
C20A | 0.0325 (14) | 0.0510 (18) | 0.0612 (19) | 0.0177 (13) | 0.0221 (13) | 0.0264 (15) |
C21A | 0.0378 (14) | 0.0497 (17) | 0.0477 (17) | 0.0244 (13) | 0.0196 (12) | 0.0222 (14) |
C22A | 0.0486 (16) | 0.0373 (16) | 0.0424 (17) | 0.0142 (13) | 0.0083 (13) | 0.0074 (13) |
C23A | 0.0402 (14) | 0.0391 (15) | 0.0398 (16) | 0.0201 (13) | 0.0064 (12) | 0.0131 (13) |
C24A | 0.0482 (16) | 0.0395 (16) | 0.0383 (17) | 0.0200 (14) | 0.0079 (13) | 0.0131 (13) |
C25A | 0.116 (3) | 0.113 (3) | 0.047 (2) | 0.089 (3) | 0.029 (2) | 0.034 (2) |
C26A | 0.133 (3) | 0.139 (4) | 0.062 (2) | 0.109 (3) | 0.045 (2) | 0.040 (2) |
C27A | 0.095 (3) | 0.075 (2) | 0.046 (2) | 0.042 (2) | 0.0287 (18) | 0.0192 (18) |
C28A | 0.091 (2) | 0.073 (2) | 0.044 (2) | 0.035 (2) | 0.0124 (18) | 0.0249 (17) |
C29A | 0.0629 (19) | 0.064 (2) | 0.0471 (19) | 0.0336 (17) | 0.0060 (15) | 0.0184 (16) |
C30A | 0.0617 (19) | 0.0474 (18) | 0.063 (2) | 0.0102 (15) | 0.0142 (15) | 0.0311 (16) |
O1B | 0.0421 (11) | 0.0569 (13) | 0.0789 (15) | 0.0238 (10) | 0.0261 (10) | 0.0349 (11) |
O2B | 0.0424 (11) | 0.0655 (14) | 0.0795 (16) | 0.0121 (11) | 0.0237 (10) | 0.0370 (12) |
N1B | 0.0355 (12) | 0.0500 (14) | 0.0385 (13) | 0.0180 (11) | 0.0070 (10) | 0.0197 (11) |
N2B | 0.0420 (14) | 0.0776 (18) | 0.0563 (17) | 0.0257 (14) | 0.0289 (12) | 0.0236 (14) |
C1B | 0.0312 (15) | 0.063 (2) | 0.0534 (19) | 0.0171 (15) | 0.0151 (13) | 0.0307 (17) |
C2B | 0.0384 (15) | 0.063 (2) | 0.0407 (17) | 0.0238 (15) | 0.0094 (13) | 0.0185 (15) |
C3B | 0.060 (2) | 0.082 (2) | 0.0449 (19) | 0.0452 (19) | 0.0188 (15) | 0.0160 (18) |
C4B | 0.068 (2) | 0.063 (2) | 0.047 (2) | 0.0404 (19) | 0.0030 (16) | 0.0030 (16) |
C5B | 0.0540 (18) | 0.0525 (19) | 0.052 (2) | 0.0214 (15) | 0.0026 (15) | 0.0103 (16) |
C6B | 0.0414 (15) | 0.0500 (18) | 0.0415 (17) | 0.0173 (14) | 0.0119 (13) | 0.0133 (14) |
C7B | 0.0398 (15) | 0.0496 (17) | 0.0335 (15) | 0.0232 (14) | 0.0097 (12) | 0.0141 (13) |
C8B | 0.0304 (13) | 0.0458 (16) | 0.0397 (16) | 0.0167 (12) | 0.0126 (11) | 0.0191 (13) |
C9B | 0.0357 (14) | 0.0380 (15) | 0.0368 (15) | 0.0169 (12) | 0.0076 (11) | 0.0153 (12) |
C10B | 0.0386 (15) | 0.0395 (15) | 0.0355 (15) | 0.0184 (13) | 0.0110 (12) | 0.0115 (12) |
C11B | 0.0442 (15) | 0.0417 (16) | 0.0370 (16) | 0.0205 (13) | 0.0121 (12) | 0.0162 (13) |
C12B | 0.0549 (17) | 0.0456 (17) | 0.0521 (18) | 0.0216 (15) | 0.0182 (14) | 0.0239 (15) |
C13B | 0.0582 (18) | 0.0472 (19) | 0.0496 (19) | 0.0214 (16) | 0.0211 (15) | 0.0236 (15) |
C14B | 0.065 (2) | 0.053 (2) | 0.082 (2) | 0.0184 (17) | 0.0153 (18) | 0.0326 (19) |
C15B | 0.091 (3) | 0.051 (2) | 0.094 (3) | 0.015 (2) | 0.013 (2) | 0.033 (2) |
C16B | 0.107 (3) | 0.059 (2) | 0.089 (3) | 0.031 (2) | 0.034 (2) | 0.045 (2) |
C17B | 0.116 (3) | 0.081 (3) | 0.070 (3) | 0.032 (3) | 0.004 (2) | 0.047 (2) |
C18B | 0.097 (3) | 0.057 (2) | 0.052 (2) | 0.014 (2) | 0.0025 (19) | 0.0265 (18) |
C19B | 0.0543 (17) | 0.0489 (18) | 0.0554 (19) | 0.0228 (15) | 0.0061 (14) | 0.0227 (15) |
C20B | 0.0393 (15) | 0.0560 (18) | 0.0534 (19) | 0.0207 (14) | 0.0039 (13) | 0.0227 (15) |
C21B | 0.0376 (15) | 0.0462 (17) | 0.0476 (18) | 0.0148 (13) | 0.0042 (13) | 0.0192 (14) |
C22B | 0.0434 (15) | 0.0467 (18) | 0.060 (2) | 0.0198 (14) | 0.0065 (14) | 0.0249 (16) |
C23B | 0.0405 (15) | 0.0441 (16) | 0.0494 (18) | 0.0202 (13) | 0.0120 (13) | 0.0204 (14) |
C24B | 0.071 (2) | 0.0383 (17) | 0.054 (2) | 0.0276 (16) | −0.0007 (16) | 0.0130 (15) |
C25B | 0.063 (2) | 0.055 (2) | 0.090 (3) | 0.0080 (18) | −0.0154 (19) | 0.024 (2) |
C26B | 0.084 (3) | 0.051 (3) | 0.155 (5) | 0.014 (2) | −0.047 (3) | 0.013 (3) |
C27B | 0.154 (5) | 0.066 (3) | 0.122 (5) | 0.063 (3) | −0.072 (4) | −0.031 (3) |
C28B | 0.174 (5) | 0.088 (4) | 0.066 (3) | 0.086 (4) | −0.018 (3) | −0.008 (3) |
C29B | 0.124 (3) | 0.064 (2) | 0.057 (2) | 0.058 (2) | 0.009 (2) | 0.009 (2) |
C30B | 0.0546 (18) | 0.079 (2) | 0.052 (2) | 0.0277 (17) | 0.0084 (15) | 0.0362 (18) |
O1A—C10A | 1.228 (3) | O1B—C10B | 1.223 (3) |
O2A—C1A | 1.214 (3) | O2B—C1B | 1.225 (3) |
N1A—C8A | 1.460 (3) | N1B—C22B | 1.468 (3) |
N1A—C22A | 1.463 (3) | N1B—C30B | 1.472 (3) |
N1A—C30A | 1.473 (3) | N1B—C8B | 1.472 (3) |
N2A—C1A | 1.359 (3) | N2B—C1B | 1.343 (4) |
N2A—C2A | 1.397 (3) | N2B—C2B | 1.397 (3) |
N2A—H2AA | 0.86 | N2B—H2BA | 0.86 |
C1A—C8A | 1.571 (3) | C1B—C8B | 1.571 (3) |
C2A—C3A | 1.377 (3) | C2B—C3B | 1.374 (4) |
C2A—C7A | 1.398 (3) | C2B—C7B | 1.400 (3) |
C3A—C4A | 1.381 (4) | C3B—C4B | 1.377 (4) |
C3A—H3AA | 0.93 | C3B—H3BA | 0.93 |
C4A—C5A | 1.377 (4) | C4B—C5B | 1.375 (4) |
C4A—H4AA | 0.93 | C4B—H4BA | 0.93 |
C5A—C6A | 1.386 (4) | C5B—C6B | 1.395 (4) |
C5A—H5AA | 0.93 | C5B—H5BA | 0.93 |
C6A—C7A | 1.385 (3) | C6B—C7B | 1.374 (3) |
C6A—H6AA | 0.93 | C6B—H6BA | 0.93 |
C7A—C8A | 1.523 (3) | C7B—C8B | 1.518 (4) |
C8A—C9A | 1.596 (3) | C8B—C9B | 1.588 (3) |
C9A—C10A | 1.535 (3) | C9B—C21B | 1.533 (3) |
C9A—C21A | 1.543 (3) | C9B—C10B | 1.552 (3) |
C9A—C23A | 1.579 (3) | C9B—C23B | 1.572 (3) |
C10A—C11A | 1.489 (3) | C10B—C11B | 1.488 (3) |
C11A—C12A | 1.332 (3) | C11B—C12B | 1.342 (3) |
C11A—C19A | 1.513 (3) | C11B—C19B | 1.515 (3) |
C12A—C13A | 1.467 (4) | C12B—C13B | 1.466 (4) |
C12A—H12A | 0.93 | C12B—H12B | 0.93 |
C13A—C18A | 1.384 (4) | C13B—C18B | 1.376 (4) |
C13A—C14A | 1.386 (4) | C13B—C14B | 1.393 (4) |
C14A—C15A | 1.383 (4) | C14B—C15B | 1.369 (4) |
C14A—H14A | 0.93 | C14B—H14B | 0.93 |
C15A—C16A | 1.367 (5) | C15B—C16B | 1.371 (5) |
C15A—H15A | 0.93 | C15B—H15B | 0.93 |
C16A—C17A | 1.356 (5) | C16B—C17B | 1.366 (5) |
C16A—H16A | 0.93 | C16B—H16B | 0.93 |
C17A—C18A | 1.369 (4) | C17B—C18B | 1.390 (4) |
C17A—H17A | 0.93 | C17B—H17B | 0.93 |
C18A—H18A | 0.93 | C18B—H18B | 0.93 |
C19A—C20A | 1.521 (3) | C19B—C20B | 1.518 (4) |
C19A—H19A | 0.97 | C19B—H19C | 0.97 |
C19A—H19B | 0.97 | C19B—H19D | 0.97 |
C20A—C21A | 1.521 (3) | C20B—C21B | 1.512 (3) |
C20A—H20A | 0.97 | C20B—H20C | 0.97 |
C20A—H20B | 0.97 | C20B—H20D | 0.97 |
C21A—H21A | 0.97 | C21B—H21C | 0.97 |
C21A—H21B | 0.97 | C21B—H21D | 0.97 |
C22A—C23A | 1.538 (3) | C22B—C23B | 1.525 (3) |
C22A—H22A | 0.97 | C22B—H22C | 0.97 |
C22A—H22B | 0.97 | C22B—H22D | 0.97 |
C23A—C24A | 1.515 (3) | C23B—C24B | 1.513 (4) |
C23A—H23A | 0.98 | C23B—H23B | 0.98 |
C24A—C25A | 1.369 (4) | C24B—C29B | 1.375 (4) |
C24A—C29A | 1.380 (3) | C24B—C25B | 1.399 (4) |
C25A—C26A | 1.385 (4) | C25B—C26B | 1.389 (5) |
C25A—H25A | 0.93 | C25B—H25B | 0.93 |
C26A—C27A | 1.359 (4) | C26B—C27B | 1.356 (7) |
C26A—H26A | 0.93 | C26B—H26B | 0.93 |
C27A—C28A | 1.339 (4) | C27B—C28B | 1.362 (7) |
C27A—H27A | 0.93 | C27B—H27B | 0.93 |
C28A—C29A | 1.393 (4) | C28B—C29B | 1.381 (5) |
C28A—H28A | 0.93 | C28B—H28B | 0.93 |
C29A—H29A | 0.93 | C29B—H29B | 0.93 |
C30A—H30A | 0.96 | C30B—H30D | 0.96 |
C30A—H30B | 0.96 | C30B—H30E | 0.96 |
C30A—H30C | 0.96 | C30B—H30F | 0.96 |
C8A—N1A—C22A | 106.6 (2) | C22B—N1B—C30B | 113.0 (2) |
C8A—N1A—C30A | 115.8 (2) | C22B—N1B—C8B | 106.5 (2) |
C22A—N1A—C30A | 113.8 (2) | C30B—N1B—C8B | 114.4 (2) |
C1A—N2A—C2A | 112.2 (2) | C1B—N2B—C2B | 112.7 (2) |
C1A—N2A—H2AA | 123.9 | C1B—N2B—H2BA | 123.6 |
C2A—N2A—H2AA | 123.9 | C2B—N2B—H2BA | 123.6 |
O2A—C1A—N2A | 124.8 (2) | O2B—C1B—N2B | 125.9 (2) |
O2A—C1A—C8A | 127.2 (2) | O2B—C1B—C8B | 126.0 (3) |
N2A—C1A—C8A | 108.0 (2) | N2B—C1B—C8B | 108.0 (2) |
C3A—C2A—N2A | 128.0 (2) | C3B—C2B—N2B | 128.1 (3) |
C3A—C2A—C7A | 122.4 (2) | C3B—C2B—C7B | 122.5 (3) |
N2A—C2A—C7A | 109.6 (2) | N2B—C2B—C7B | 109.3 (2) |
C2A—C3A—C4A | 117.8 (3) | C2B—C3B—C4B | 118.0 (3) |
C2A—C3A—H3AA | 121.1 | C2B—C3B—H3BA | 121.0 |
C4A—C3A—H3AA | 121.1 | C4B—C3B—H3BA | 121.0 |
C5A—C4A—C3A | 120.9 (3) | C5B—C4B—C3B | 120.9 (3) |
C5A—C4A—H4AA | 119.5 | C5B—C4B—H4BA | 119.6 |
C3A—C4A—H4AA | 119.5 | C3B—C4B—H4BA | 119.6 |
C4A—C5A—C6A | 120.9 (3) | C4B—C5B—C6B | 120.6 (3) |
C4A—C5A—H5AA | 119.5 | C4B—C5B—H5BA | 119.7 |
C6A—C5A—H5AA | 119.5 | C6B—C5B—H5BA | 119.7 |
C7A—C6A—C5A | 119.3 (2) | C7B—C6B—C5B | 119.6 (3) |
C7A—C6A—H6AA | 120.4 | C7B—C6B—H6BA | 120.2 |
C5A—C6A—H6AA | 120.4 | C5B—C6B—H6BA | 120.2 |
C6A—C7A—C2A | 118.6 (2) | C6B—C7B—C2B | 118.4 (3) |
C6A—C7A—C8A | 131.9 (2) | C6B—C7B—C8B | 132.3 (2) |
C2A—C7A—C8A | 109.4 (2) | C2B—C7B—C8B | 109.1 (2) |
N1A—C8A—C7A | 112.32 (19) | N1B—C8B—C7B | 110.90 (19) |
N1A—C8A—C1A | 113.03 (19) | N1B—C8B—C1B | 111.46 (19) |
C7A—C8A—C1A | 100.61 (19) | C7B—C8B—C1B | 100.8 (2) |
N1A—C8A—C9A | 101.25 (17) | N1B—C8B—C9B | 102.11 (19) |
C7A—C8A—C9A | 118.94 (19) | C7B—C8B—C9B | 120.28 (19) |
C1A—C8A—C9A | 111.22 (19) | C1B—C8B—C9B | 111.53 (19) |
C10A—C9A—C21A | 109.54 (19) | C21B—C9B—C10B | 109.3 (2) |
C10A—C9A—C23A | 107.86 (19) | C21B—C9B—C23B | 114.4 (2) |
C21A—C9A—C23A | 113.5 (2) | C10B—C9B—C23B | 108.7 (2) |
C10A—C9A—C8A | 107.22 (19) | C21B—C9B—C8B | 114.03 (19) |
C21A—C9A—C8A | 114.83 (19) | C10B—C9B—C8B | 106.42 (18) |
C23A—C9A—C8A | 103.37 (18) | C23B—C9B—C8B | 103.58 (18) |
O1A—C10A—C11A | 119.0 (2) | O1B—C10B—C11B | 120.3 (2) |
O1A—C10A—C9A | 119.2 (2) | O1B—C10B—C9B | 119.0 (2) |
C11A—C10A—C9A | 121.8 (2) | C11B—C10B—C9B | 120.6 (2) |
C12A—C11A—C10A | 116.3 (2) | C12B—C11B—C10B | 116.9 (2) |
C12A—C11A—C19A | 124.6 (2) | C12B—C11B—C19B | 123.0 (2) |
C10A—C11A—C19A | 119.1 (2) | C10B—C11B—C19B | 120.1 (2) |
C11A—C12A—C13A | 127.9 (2) | C11B—C12B—C13B | 129.7 (3) |
C11A—C12A—H12A | 116.1 | C11B—C12B—H12B | 115.1 |
C13A—C12A—H12A | 116.1 | C13B—C12B—H12B | 115.1 |
C18A—C13A—C14A | 117.4 (3) | C18B—C13B—C14B | 117.6 (3) |
C18A—C13A—C12A | 122.4 (3) | C18B—C13B—C12B | 123.9 (3) |
C14A—C13A—C12A | 119.9 (2) | C14B—C13B—C12B | 118.5 (3) |
C15A—C14A—C13A | 119.9 (3) | C15B—C14B—C13B | 121.2 (3) |
C15A—C14A—H14A | 120.0 | C15B—C14B—H14B | 119.4 |
C13A—C14A—H14A | 120.0 | C13B—C14B—H14B | 119.4 |
C16A—C15A—C14A | 121.2 (4) | C14B—C15B—C16B | 120.5 (3) |
C16A—C15A—H15A | 119.4 | C14B—C15B—H15B | 119.7 |
C14A—C15A—H15A | 119.4 | C16B—C15B—H15B | 119.7 |
C17A—C16A—C15A | 119.2 (3) | C17B—C16B—C15B | 119.4 (3) |
C17A—C16A—H16A | 120.4 | C17B—C16B—H16B | 120.3 |
C15A—C16A—H16A | 120.4 | C15B—C16B—H16B | 120.3 |
C16A—C17A—C18A | 120.3 (3) | C16B—C17B—C18B | 120.3 (3) |
C16A—C17A—H17A | 119.8 | C16B—C17B—H17B | 119.8 |
C18A—C17A—H17A | 119.8 | C18B—C17B—H17B | 119.8 |
C17A—C18A—C13A | 121.8 (3) | C13B—C18B—C17B | 120.9 (3) |
C17A—C18A—H18A | 119.1 | C13B—C18B—H18B | 119.5 |
C13A—C18A—H18A | 119.1 | C17B—C18B—H18B | 119.5 |
C11A—C19A—C20A | 111.5 (2) | C11B—C19B—C20B | 113.4 (2) |
C11A—C19A—H19A | 109.3 | C11B—C19B—H19C | 108.9 |
C20A—C19A—H19A | 109.3 | C20B—C19B—H19C | 108.9 |
C11A—C19A—H19B | 109.3 | C11B—C19B—H19D | 108.9 |
C20A—C19A—H19B | 109.3 | C20B—C19B—H19D | 108.9 |
H19A—C19A—H19B | 108.0 | H19C—C19B—H19D | 107.7 |
C21A—C20A—C19A | 110.0 (2) | C21B—C20B—C19B | 110.2 (2) |
C21A—C20A—H20A | 109.7 | C21B—C20B—H20C | 109.6 |
C19A—C20A—H20A | 109.7 | C19B—C20B—H20C | 109.6 |
C21A—C20A—H20B | 109.7 | C21B—C20B—H20D | 109.6 |
C19A—C20A—H20B | 109.7 | C19B—C20B—H20D | 109.6 |
H20A—C20A—H20B | 108.2 | H20C—C20B—H20D | 108.1 |
C20A—C21A—C9A | 113.9 (2) | C20B—C21B—C9B | 113.3 (2) |
C20A—C21A—H21A | 108.8 | C20B—C21B—H21C | 108.9 |
C9A—C21A—H21A | 108.8 | C9B—C21B—H21C | 108.9 |
C20A—C21A—H21B | 108.8 | C20B—C21B—H21D | 108.9 |
C9A—C21A—H21B | 108.8 | C9B—C21B—H21D | 108.9 |
H21A—C21A—H21B | 107.7 | H21C—C21B—H21D | 107.7 |
N1A—C22A—C23A | 104.15 (19) | N1B—C22B—C23B | 103.7 (2) |
N1A—C22A—H22A | 110.9 | N1B—C22B—H22C | 111.0 |
C23A—C22A—H22A | 110.9 | C23B—C22B—H22C | 111.0 |
N1A—C22A—H22B | 110.9 | N1B—C22B—H22D | 111.0 |
C23A—C22A—H22B | 110.9 | C23B—C22B—H22D | 111.0 |
H22A—C22A—H22B | 108.9 | H22C—C22B—H22D | 109.0 |
C24A—C23A—C22A | 114.4 (2) | C24B—C23B—C22B | 114.4 (2) |
C24A—C23A—C9A | 118.9 (2) | C24B—C23B—C9B | 117.2 (2) |
C22A—C23A—C9A | 104.74 (19) | C22B—C23B—C9B | 105.6 (2) |
C24A—C23A—H23A | 105.9 | C24B—C23B—H23B | 106.3 |
C22A—C23A—H23A | 105.9 | C22B—C23B—H23B | 106.3 |
C9A—C23A—H23A | 105.9 | C9B—C23B—H23B | 106.3 |
C25A—C24A—C29A | 116.8 (3) | C29B—C24B—C25B | 117.3 (3) |
C25A—C24A—C23A | 124.2 (2) | C29B—C24B—C23B | 120.1 (3) |
C29A—C24A—C23A | 119.0 (2) | C25B—C24B—C23B | 122.6 (3) |
C24A—C25A—C26A | 121.5 (3) | C26B—C25B—C24B | 120.0 (4) |
C24A—C25A—H25A | 119.2 | C26B—C25B—H25B | 120.0 |
C26A—C25A—H25A | 119.2 | C24B—C25B—H25B | 120.0 |
C27A—C26A—C25A | 120.5 (3) | C27B—C26B—C25B | 121.3 (5) |
C27A—C26A—H26A | 119.7 | C27B—C26B—H26B | 119.3 |
C25A—C26A—H26A | 119.7 | C25B—C26B—H26B | 119.3 |
C28A—C27A—C26A | 119.2 (3) | C26B—C27B—C28B | 119.1 (5) |
C28A—C27A—H27A | 120.4 | C26B—C27B—H27B | 120.4 |
C26A—C27A—H27A | 120.4 | C28B—C27B—H27B | 120.4 |
C27A—C28A—C29A | 120.8 (3) | C27B—C28B—C29B | 120.5 (5) |
C27A—C28A—H28A | 119.6 | C27B—C28B—H28B | 119.7 |
C29A—C28A—H28A | 119.6 | C29B—C28B—H28B | 119.7 |
C24A—C29A—C28A | 121.1 (3) | C24B—C29B—C28B | 121.6 (4) |
C24A—C29A—H29A | 119.5 | C24B—C29B—H29B | 119.2 |
C28A—C29A—H29A | 119.5 | C28B—C29B—H29B | 119.2 |
N1A—C30A—H30A | 109.5 | N1B—C30B—H30D | 109.5 |
N1A—C30A—H30B | 109.5 | N1B—C30B—H30E | 109.5 |
H30A—C30A—H30B | 109.5 | H30D—C30B—H30E | 109.5 |
N1A—C30A—H30C | 109.5 | N1B—C30B—H30F | 109.5 |
H30A—C30A—H30C | 109.5 | H30D—C30B—H30F | 109.5 |
H30B—C30A—H30C | 109.5 | H30E—C30B—H30F | 109.5 |
C2A—N2A—C1A—O2A | −174.4 (2) | C2B—N2B—C1B—O2B | 175.6 (3) |
C2A—N2A—C1A—C8A | 4.7 (3) | C2B—N2B—C1B—C8B | −1.3 (3) |
C1A—N2A—C2A—C3A | 175.0 (2) | C1B—N2B—C2B—C3B | −175.4 (3) |
C1A—N2A—C2A—C7A | −3.3 (3) | C1B—N2B—C2B—C7B | 1.2 (3) |
N2A—C2A—C3A—C4A | −176.7 (2) | N2B—C2B—C3B—C4B | 175.7 (3) |
C7A—C2A—C3A—C4A | 1.4 (4) | C7B—C2B—C3B—C4B | −0.4 (4) |
C2A—C3A—C4A—C5A | −0.4 (4) | C2B—C3B—C4B—C5B | −0.3 (4) |
C3A—C4A—C5A—C6A | 0.7 (4) | C3B—C4B—C5B—C6B | 0.3 (4) |
C4A—C5A—C6A—C7A | −2.0 (4) | C4B—C5B—C6B—C7B | 0.4 (4) |
C5A—C6A—C7A—C2A | 2.9 (4) | C5B—C6B—C7B—C2B | −1.1 (4) |
C5A—C6A—C7A—C8A | 177.0 (2) | C5B—C6B—C7B—C8B | −174.9 (3) |
C3A—C2A—C7A—C6A | −2.7 (4) | C3B—C2B—C7B—C6B | 1.1 (4) |
N2A—C2A—C7A—C6A | 175.7 (2) | N2B—C2B—C7B—C6B | −175.7 (2) |
C3A—C2A—C7A—C8A | −178.0 (2) | C3B—C2B—C7B—C8B | 176.3 (2) |
N2A—C2A—C7A—C8A | 0.4 (3) | N2B—C2B—C7B—C8B | −0.5 (3) |
C22A—N1A—C8A—C7A | 172.73 (19) | C22B—N1B—C8B—C7B | −171.4 (2) |
C30A—N1A—C8A—C7A | −59.6 (3) | C30B—N1B—C8B—C7B | 63.1 (3) |
C22A—N1A—C8A—C1A | −74.3 (2) | C22B—N1B—C8B—C1B | 77.1 (3) |
C30A—N1A—C8A—C1A | 53.4 (3) | C30B—N1B—C8B—C1B | −48.4 (3) |
C22A—N1A—C8A—C9A | 44.8 (2) | C22B—N1B—C8B—C9B | −42.1 (2) |
C30A—N1A—C8A—C9A | 172.5 (2) | C30B—N1B—C8B—C9B | −167.60 (19) |
C6A—C7A—C8A—N1A | −51.8 (3) | C6B—C7B—C8B—N1B | 55.9 (3) |
C2A—C7A—C8A—N1A | 122.6 (2) | C2B—C7B—C8B—N1B | −118.4 (2) |
C6A—C7A—C8A—C1A | −172.3 (2) | C6B—C7B—C8B—C1B | 174.0 (3) |
C2A—C7A—C8A—C1A | 2.2 (2) | C2B—C7B—C8B—C1B | −0.3 (2) |
C6A—C7A—C8A—C9A | 66.1 (3) | C6B—C7B—C8B—C9B | −63.0 (4) |
C2A—C7A—C8A—C9A | −119.5 (2) | C2B—C7B—C8B—C9B | 122.7 (2) |
O2A—C1A—C8A—N1A | 55.1 (3) | O2B—C1B—C8B—N1B | −58.2 (3) |
N2A—C1A—C8A—N1A | −124.0 (2) | N2B—C1B—C8B—N1B | 118.7 (2) |
O2A—C1A—C8A—C7A | 175.0 (2) | O2B—C1B—C8B—C7B | −175.9 (3) |
N2A—C1A—C8A—C7A | −4.1 (2) | N2B—C1B—C8B—C7B | 0.9 (3) |
O2A—C1A—C8A—C9A | −58.0 (3) | O2B—C1B—C8B—C9B | 55.2 (3) |
N2A—C1A—C8A—C9A | 122.8 (2) | N2B—C1B—C8B—C9B | −127.9 (2) |
N1A—C8A—C9A—C10A | 84.8 (2) | N1B—C8B—C9B—C21B | 149.49 (19) |
C7A—C8A—C9A—C10A | −38.7 (3) | C7B—C8B—C9B—C21B | −87.3 (3) |
C1A—C8A—C9A—C10A | −154.8 (2) | C1B—C8B—C9B—C21B | 30.4 (3) |
N1A—C8A—C9A—C21A | −153.2 (2) | N1B—C8B—C9B—C10B | −89.9 (2) |
C7A—C8A—C9A—C21A | 83.2 (3) | C7B—C8B—C9B—C10B | 33.3 (3) |
C1A—C8A—C9A—C21A | −32.9 (3) | C1B—C8B—C9B—C10B | 150.9 (2) |
N1A—C8A—C9A—C23A | −29.0 (2) | N1B—C8B—C9B—C23B | 24.5 (2) |
C7A—C8A—C9A—C23A | −152.5 (2) | C7B—C8B—C9B—C23B | 147.7 (2) |
C1A—C8A—C9A—C23A | 91.3 (2) | C1B—C8B—C9B—C23B | −94.6 (2) |
C21A—C9A—C10A—O1A | 157.1 (2) | C21B—C9B—C10B—O1B | −156.2 (2) |
C23A—C9A—C10A—O1A | 33.1 (3) | C23B—C9B—C10B—O1B | −30.8 (3) |
C8A—C9A—C10A—O1A | −77.6 (3) | C8B—C9B—C10B—O1B | 80.2 (3) |
C21A—C9A—C10A—C11A | −24.6 (3) | C21B—C9B—C10B—C11B | 25.7 (3) |
C23A—C9A—C10A—C11A | −148.7 (2) | C23B—C9B—C10B—C11B | 151.2 (2) |
C8A—C9A—C10A—C11A | 100.6 (2) | C8B—C9B—C10B—C11B | −97.9 (2) |
O1A—C10A—C11A—C12A | 19.8 (3) | O1B—C10B—C11B—C12B | −13.8 (4) |
C9A—C10A—C11A—C12A | −158.5 (2) | C9B—C10B—C11B—C12B | 164.3 (2) |
O1A—C10A—C11A—C19A | −162.5 (2) | O1B—C10B—C11B—C19B | 168.4 (2) |
C9A—C10A—C11A—C19A | 19.3 (3) | C9B—C10B—C11B—C19B | −13.6 (3) |
C10A—C11A—C12A—C13A | −176.8 (2) | C10B—C11B—C12B—C13B | −179.5 (2) |
C19A—C11A—C12A—C13A | 5.5 (4) | C19B—C11B—C12B—C13B | −1.7 (4) |
C11A—C12A—C13A—C18A | 51.0 (4) | C11B—C12B—C13B—C18B | −39.5 (4) |
C11A—C12A—C13A—C14A | −134.9 (3) | C11B—C12B—C13B—C14B | 142.6 (3) |
C18A—C13A—C14A—C15A | −2.9 (4) | C18B—C13B—C14B—C15B | 1.6 (5) |
C12A—C13A—C14A—C15A | −177.4 (3) | C12B—C13B—C14B—C15B | 179.7 (3) |
C13A—C14A—C15A—C16A | 2.6 (5) | C13B—C14B—C15B—C16B | −0.6 (5) |
C14A—C15A—C16A—C17A | −0.8 (5) | C14B—C15B—C16B—C17B | −0.3 (6) |
C15A—C16A—C17A—C18A | −0.6 (5) | C15B—C16B—C17B—C18B | 0.2 (6) |
C16A—C17A—C18A—C13A | 0.1 (5) | C14B—C13B—C18B—C17B | −1.8 (5) |
C14A—C13A—C18A—C17A | 1.7 (4) | C12B—C13B—C18B—C17B | −179.7 (3) |
C12A—C13A—C18A—C17A | 175.9 (3) | C16B—C17B—C18B—C13B | 0.9 (5) |
C12A—C11A—C19A—C20A | 144.4 (3) | C12B—C11B—C19B—C20B | −153.1 (3) |
C10A—C11A—C19A—C20A | −33.2 (3) | C10B—C11B—C19B—C20B | 24.6 (3) |
C11A—C19A—C20A—C21A | 54.3 (3) | C11B—C19B—C20B—C21B | −48.9 (3) |
C19A—C20A—C21A—C9A | −64.3 (3) | C19B—C20B—C21B—C9B | 65.5 (3) |
C10A—C9A—C21A—C20A | 46.9 (3) | C10B—C9B—C21B—C20B | −51.6 (3) |
C23A—C9A—C21A—C20A | 167.5 (2) | C23B—C9B—C21B—C20B | −173.7 (2) |
C8A—C9A—C21A—C20A | −73.8 (3) | C8B—C9B—C21B—C20B | 67.3 (3) |
C8A—N1A—C22A—C23A | −42.7 (2) | C30B—N1B—C22B—C23B | 169.15 (19) |
C30A—N1A—C22A—C23A | −171.6 (2) | C8B—N1B—C22B—C23B | 42.8 (2) |
N1A—C22A—C23A—C24A | 153.2 (2) | N1B—C22B—C23B—C24B | −155.2 (2) |
N1A—C22A—C23A—C9A | 21.3 (2) | N1B—C22B—C23B—C9B | −24.8 (3) |
C10A—C9A—C23A—C24A | 122.1 (2) | C21B—C9B—C23B—C24B | 4.0 (3) |
C21A—C9A—C23A—C24A | 0.5 (3) | C10B—C9B—C23B—C24B | −118.4 (3) |
C8A—C9A—C23A—C24A | −124.6 (2) | C8B—C9B—C23B—C24B | 128.7 (2) |
C10A—C9A—C23A—C22A | −108.6 (2) | C21B—C9B—C23B—C22B | −124.7 (2) |
C21A—C9A—C23A—C22A | 129.8 (2) | C10B—C9B—C23B—C22B | 112.9 (2) |
C8A—C9A—C23A—C22A | 4.8 (2) | C8B—C9B—C23B—C22B | 0.0 (2) |
C22A—C23A—C24A—C25A | −48.2 (4) | C22B—C23B—C24B—C29B | −132.8 (3) |
C9A—C23A—C24A—C25A | 76.5 (3) | C9B—C23B—C24B—C29B | 102.8 (3) |
C22A—C23A—C24A—C29A | 129.4 (3) | C22B—C23B—C24B—C25B | 45.6 (4) |
C9A—C23A—C24A—C29A | −105.9 (3) | C9B—C23B—C24B—C25B | −78.8 (3) |
C29A—C24A—C25A—C26A | 0.9 (5) | C29B—C24B—C25B—C26B | 0.1 (5) |
C23A—C24A—C25A—C26A | 178.6 (3) | C23B—C24B—C25B—C26B | −178.3 (3) |
C24A—C25A—C26A—C27A | −1.6 (6) | C24B—C25B—C26B—C27B | 0.3 (6) |
C25A—C26A—C27A—C28A | 1.5 (6) | C25B—C26B—C27B—C28B | −1.9 (7) |
C26A—C27A—C28A—C29A | −0.8 (5) | C26B—C27B—C28B—C29B | 3.3 (7) |
C25A—C24A—C29A—C28A | −0.1 (4) | C25B—C24B—C29B—C28B | 1.3 (5) |
C23A—C24A—C29A—C28A | −177.9 (3) | C23B—C24B—C29B—C28B | 179.7 (3) |
C27A—C28A—C29A—C24A | 0.1 (5) | C27B—C28B—C29B—C24B | −3.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12A—H12A···O1A | 0.93 | 2.33 | 2.704 (3) | 103 |
C12B—H12B···O1B | 0.93 | 2.34 | 2.730 (3) | 105 |
C23A—H23A···O1A | 0.98 | 2.23 | 2.751 (3) | 112 |
C23B—H23B···O1B | 0.98 | 2.23 | 2.764 (3) | 113 |
N2A—H2AA···N1Bi | 0.86 | 2.33 | 3.029 (3) | 139 |
N2B—H2BA···O1Aii | 0.86 | 2.06 | 2.848 (3) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C30H28N2O2 |
Mr | 448.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 12.3624 (1), 13.0640 (2), 17.1439 (3) |
α, β, γ (°) | 110.066 (1), 93.200 (1), 110.534 (1) |
V (Å3) | 2386.13 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.36 × 0.24 × 0.16 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.972, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13509, 8228, 4402 |
Rint | 0.064 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.141, 0.88 |
No. of reflections | 8228 |
No. of parameters | 616 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.26 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
N1A—C8A | 1.460 (3) | N1B—C22B | 1.468 (3) |
N1A—C22A | 1.463 (3) | N1B—C30B | 1.472 (3) |
N1A—C30A | 1.473 (3) | N1B—C8B | 1.472 (3) |
N2A—C1A | 1.359 (3) | N2B—C1B | 1.343 (4) |
N2A—C2A | 1.397 (3) | N2B—C2B | 1.397 (3) |
C11A—C12A | 1.332 (3) | ||
C8A—N1A—C22A | 106.6 (2) | C22B—N1B—C30B | 113.0 (2) |
C8A—N1A—C30A | 115.8 (2) | C22B—N1B—C8B | 106.5 (2) |
C22A—N1A—C30A | 113.8 (2) | C30B—N1B—C8B | 114.4 (2) |
C10A—C11A—C12A—C13A | −176.8 (2) | C10B—C11B—C12B—C13B | −179.5 (2) |
C11A—C12A—C13A—C18A | 51.0 (4) | C11B—C12B—C13B—C18B | −39.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12A—H12A···O1A | 0.93 | 2.33 | 2.704 (3) | 103 |
C12B—H12B···O1B | 0.93 | 2.34 | 2.730 (3) | 105 |
C23A—H23A···O1A | 0.98 | 2.23 | 2.751 (3) | 112 |
C23B—H23B···O1B | 0.98 | 2.23 | 2.764 (3) | 113 |
N2A—H2AA···N1Bi | 0.86 | 2.33 | 3.029 (3) | 139 |
N2B—H2BA···O1Aii | 0.86 | 2.06 | 2.848 (3) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
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Substituted pyrrolidine compounds have gained much importance since they are the basic structural elements of many alkaloids and pharmacologically active compounds, while molecules with indole moiety possess anti-inflammatory and antibacterial properties. Our interest on preparing the pharmacologically active pyrrolidine compounds led us to the title compound, (I), and we have undertaken an X-ray crystal structure determination of (I) in order to establish the conformation of the structure.
In the title structure, the asymmetric unit contains an enantiomeric pair of molecules (A and B) with almost identical geometry, except for the rotation of the phenyl rings about the C12—C13 bond. In the two molecules, the bond lengths and angles show normal values (Allen et al., 1987) and agree with each other. The values within the oxindole moiety are slightly different compared with those of the indole derivative (Zukerman-Schpector, 1992), especially with regard to the longer C1—C8 and C7—C8 bond lengths, due to the spiro-atom character and the steric effect of the bulky group substituted at C8. The arguments can also be applied to the longer C—C and C—N bond lengths within the pyrrolidine ring, while the N1 atom is in a pyramidal configuration (Perales et al., 1977), compared with those of the pyrrolidine ring in a previous study (Gzella & Wrzeciono, 1990). The average C—C bond distance in the cyclohexane ring is 1.520 (4) Å in the two molecules.
In both molecules A and B, the pyrrolidine ring adopts an envelope conformation and the cyclohexane ring is in a half-chair conformation, with a dihedral angle between them of 84.3 (1)° in molecule A and 85.3 (1)° in molecule B. The conformations were confirmed by their puckering parameters (Cremer & Pople, 1975); for the pyrrolidine ring Q2 = 0.420 (3) Å and ϕ2 = 187.4 (4)° in molecule A and Q2 = 0.405 (3) Å and ϕ2 = 0.7 (4)° in molecule B, while for the cyclohexane ring, Q2 = 0.281 (3), Q3 = 0.403 (3), QT = 0.491 (3) Å and ϕ2 = 258.6 (6)° in molecule A, and Q2 = 0.311 (3), Q3 = -0.381 (3), QT = 0.492 (3) Å and ϕ2 = 93.1 (5)° in molecule B. The phenyl ring attached at C23 is in a bisectional configuration with respect to the pyrrolidine ring in both molecules, corresponding to a dihedral angle between the phenyl and pyrrolidine rings of 83.6 (2)° in molecule A and 81.4 (2)° in molecule B. The phenyl ring attached at C12 makes dihedral angles of 63.2 (2) and 46.2 (2)° with the cyclohexane ring in molecules A and B, respectively. In the oxindole moiety, the phenyl and pyrrole rings are individually planar and make a dihedral angle of 4.1 (2) and 4.2 (2)° in molecule A and B, respectively, while the attached O2A and O2B atoms deviate by -0.204 (2) and 0.171 (2) Å, respectively, from the mean planes of the oxindole moieties in the two molecules. The oxindole moiety makes dihedral angles of 89.9 (1) and 87.8 (1)° with the pyrrolidine ring in molecules A and B, respectively, corresponding to nearly perpendicular configurations.
The closest distances of C12···O1 and C23···O1 are within 2.764 (3) Å (Table 2), implying intramolecular non-bonded hydrogen interactions and forming closed O1—C10—C11—C12—H12 and O1—C10—C9—C23—H23 rings. These interactions stabilize the molecular structure, while the observed intermolecular N—H···N and N—H···O (Table 2) interactions interconnecting molecules A and B in different asymmetric units, as well as van der Waals interactions, stabilize the crystal structure.