Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054803/ng2358sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054803/ng2358Isup2.hkl |
CCDC reference: 672846
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.057
- wR factor = 0.136
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C28
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of the title compound, see: Yin et al. (2006). For the structure of cucurbit[6]uril, see Freeman et al. (1981). For literature on clip molecules based on glycoluril, see Chen et al. (2007); Hu et al. (2007); Li et al. (2006); Rowan et al. (1999); She et al. (2007); Wang et al. (2006).
The title compound was synthesized according to the reported literature (Yin et al., 2006). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (4:1) solution of the title compound under ambient conditions.
One of the ethyl groups (C15) was found to be disordered over two orientations. The occupancies of the disordered positions C15/C15' refined to 0.64 (2):0.36 (2). All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, allowing for free rotation of the methyl groups. The constraint Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) (methyl C) was applied.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
Fig. 1. A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. |
C28H32N6O6 | F(000) = 2320 |
Mr = 548.60 | Dx = 1.350 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ac2ab | Cell parameters from 4426 reflections |
a = 17.8591 (13) Å | θ = 2.6–21.8° |
b = 15.4533 (11) Å | µ = 0.10 mm−1 |
c = 19.5649 (14) Å | T = 292 K |
V = 5399.6 (7) Å3 | Block, colorless |
Z = 8 | 0.30 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 4406 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
ϕ and ω scans | h = −22→22 |
30333 measured reflections | k = −19→19 |
5874 independent reflections | l = −16→24 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0501P)2 + 2.134P] where P = (Fo2 + 2Fc2)/3 |
5874 reflections | (Δ/σ)max = 0.001 |
370 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
C28H32N6O6 | V = 5399.6 (7) Å3 |
Mr = 548.60 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 17.8591 (13) Å | µ = 0.10 mm−1 |
b = 15.4533 (11) Å | T = 292 K |
c = 19.5649 (14) Å | 0.30 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 4406 reflections with I > 2σ(I) |
30333 measured reflections | Rint = 0.050 |
5874 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 1 restraint |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.21 e Å−3 |
5874 reflections | Δρmin = −0.19 e Å−3 |
370 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.13577 (17) | 0.19168 (16) | 0.46245 (14) | 0.0655 (8) | |
H1A | 0.1142 | 0.1880 | 0.5073 | 0.098* | |
H1B | 0.1873 | 0.1741 | 0.4643 | 0.098* | |
H1C | 0.1089 | 0.1544 | 0.4318 | 0.098* | |
C2 | 0.13103 (13) | 0.28371 (14) | 0.43719 (11) | 0.0462 (6) | |
C3 | 0.07028 (14) | 0.33474 (17) | 0.45309 (14) | 0.0568 (7) | |
H3 | 0.0317 | 0.3121 | 0.4796 | 0.068* | |
C4 | 0.06592 (14) | 0.41882 (17) | 0.43031 (14) | 0.0579 (7) | |
H4 | 0.0245 | 0.4524 | 0.4415 | 0.069* | |
C5 | 0.12232 (12) | 0.45357 (15) | 0.39119 (12) | 0.0465 (6) | |
H5 | 0.1188 | 0.5104 | 0.3758 | 0.056* | |
C6 | 0.18480 (11) | 0.40391 (13) | 0.37455 (10) | 0.0360 (5) | |
C7 | 0.18868 (12) | 0.31908 (14) | 0.39802 (11) | 0.0406 (5) | |
H7 | 0.2303 | 0.2855 | 0.3874 | 0.049* | |
C8 | 0.29814 (12) | 0.38598 (13) | 0.30343 (11) | 0.0378 (5) | |
H8A | 0.3318 | 0.3658 | 0.3389 | 0.045* | |
H8B | 0.2745 | 0.3360 | 0.2826 | 0.045* | |
C9 | 0.27758 (12) | 0.51778 (13) | 0.36519 (10) | 0.0372 (5) | |
H9A | 0.2400 | 0.5548 | 0.3857 | 0.045* | |
H9B | 0.3110 | 0.4982 | 0.4010 | 0.045* | |
C10 | 0.31559 (11) | 0.43743 (13) | 0.18532 (11) | 0.0349 (5) | |
C11 | 0.28227 (11) | 0.62743 (12) | 0.27600 (10) | 0.0314 (4) | |
C12 | 0.37140 (11) | 0.51700 (12) | 0.27303 (10) | 0.0322 (4) | |
C13 | 0.44683 (11) | 0.50352 (14) | 0.30994 (11) | 0.0386 (5) | |
C14 | 0.57290 (13) | 0.45747 (18) | 0.29232 (14) | 0.0607 (7) | |
H14A | 0.5853 | 0.5060 | 0.3217 | 0.073* | 0.64 (2) |
H14B | 0.6069 | 0.4583 | 0.2537 | 0.073* | 0.64 (2) |
H14C | 0.6071 | 0.4865 | 0.2614 | 0.073* | 0.36 (2) |
H14D | 0.5781 | 0.4834 | 0.3372 | 0.073* | 0.36 (2) |
C15 | 0.5831 (5) | 0.3757 (6) | 0.3308 (8) | 0.081 (3) | 0.64 (2) |
H15A | 0.5519 | 0.3763 | 0.3707 | 0.122* | 0.64 (2) |
H15B | 0.6346 | 0.3702 | 0.3443 | 0.122* | 0.64 (2) |
H15C | 0.5695 | 0.3277 | 0.3023 | 0.122* | 0.64 (2) |
C15' | 0.5909 (11) | 0.3650 (8) | 0.2959 (12) | 0.081 (3) | 0.36 (2) |
H15D | 0.5555 | 0.3364 | 0.3252 | 0.122* | 0.36 (2) |
H15E | 0.6404 | 0.3577 | 0.3140 | 0.122* | 0.36 (2) |
H15F | 0.5884 | 0.3403 | 0.2510 | 0.122* | 0.36 (2) |
C16 | 0.37500 (11) | 0.56958 (12) | 0.20477 (10) | 0.0319 (4) | |
C17 | 0.45154 (11) | 0.60894 (14) | 0.18663 (11) | 0.0385 (5) | |
C18 | 0.54944 (13) | 0.69342 (17) | 0.23643 (15) | 0.0600 (7) | |
H18A | 0.5502 | 0.7369 | 0.2006 | 0.072* | |
H18B | 0.5875 | 0.6505 | 0.2265 | 0.072* | |
C19 | 0.56359 (17) | 0.7339 (2) | 0.30383 (16) | 0.0811 (10) | |
H19A | 0.5264 | 0.7774 | 0.3124 | 0.122* | |
H19B | 0.6124 | 0.7600 | 0.3039 | 0.122* | |
H19C | 0.5611 | 0.6905 | 0.3389 | 0.122* | |
C20 | 0.31026 (12) | 0.54585 (14) | 0.09478 (10) | 0.0404 (5) | |
H20A | 0.2874 | 0.5001 | 0.0681 | 0.048* | |
H20B | 0.3463 | 0.5756 | 0.0661 | 0.048* | |
C21 | 0.28691 (12) | 0.67668 (12) | 0.15651 (10) | 0.0361 (5) | |
H21A | 0.3239 | 0.7061 | 0.1286 | 0.043* | |
H21B | 0.2491 | 0.7184 | 0.1700 | 0.043* | |
C22 | 0.19878 (11) | 0.63132 (14) | 0.06778 (10) | 0.0365 (5) | |
C23 | 0.15080 (13) | 0.56850 (16) | 0.04217 (11) | 0.0483 (6) | |
H23 | 0.1561 | 0.5111 | 0.0555 | 0.058* | |
C24 | 0.09497 (14) | 0.59180 (19) | −0.00343 (13) | 0.0583 (7) | |
H24 | 0.0621 | 0.5500 | −0.0199 | 0.070* | |
C25 | 0.08790 (13) | 0.67635 (19) | −0.02449 (12) | 0.0563 (7) | |
H25 | 0.0507 | 0.6909 | −0.0557 | 0.068* | |
C26 | 0.13505 (12) | 0.73984 (17) | −0.00012 (12) | 0.0483 (6) | |
C27 | 0.19051 (12) | 0.71622 (14) | 0.04632 (11) | 0.0406 (5) | |
H27 | 0.2227 | 0.7584 | 0.0633 | 0.049* | |
C28 | 0.12859 (16) | 0.8322 (2) | −0.02293 (17) | 0.0790 (9) | |
H28A | 0.1743 | 0.8496 | −0.0448 | 0.118* | |
H28B | 0.1195 | 0.8685 | 0.0160 | 0.118* | |
H28C | 0.0878 | 0.8376 | −0.0546 | 0.118* | |
N1 | 0.24122 (9) | 0.44287 (10) | 0.33290 (9) | 0.0364 (4) | |
N2 | 0.33984 (9) | 0.43436 (10) | 0.25214 (8) | 0.0325 (4) | |
N3 | 0.31940 (9) | 0.56596 (10) | 0.31470 (8) | 0.0320 (4) | |
N4 | 0.34792 (9) | 0.50907 (10) | 0.15396 (8) | 0.0343 (4) | |
N5 | 0.32233 (9) | 0.63989 (10) | 0.21670 (8) | 0.0306 (4) | |
N6 | 0.25262 (10) | 0.60692 (10) | 0.11782 (8) | 0.0364 (4) | |
O1 | 0.27578 (9) | 0.38472 (9) | 0.15775 (8) | 0.0469 (4) | |
O2 | 0.22632 (8) | 0.66624 (9) | 0.29289 (8) | 0.0422 (4) | |
O3 | 0.45827 (9) | 0.52344 (12) | 0.36771 (8) | 0.0553 (4) | |
O4 | 0.49553 (8) | 0.46721 (11) | 0.26752 (8) | 0.0544 (4) | |
O5 | 0.48131 (9) | 0.60350 (13) | 0.13262 (9) | 0.0622 (5) | |
O6 | 0.47578 (8) | 0.65276 (10) | 0.24036 (8) | 0.0481 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.079 (2) | 0.0484 (14) | 0.0691 (18) | −0.0121 (13) | 0.0201 (15) | 0.0033 (13) |
C2 | 0.0509 (14) | 0.0436 (12) | 0.0441 (13) | −0.0091 (11) | 0.0080 (11) | −0.0035 (10) |
C3 | 0.0470 (14) | 0.0571 (15) | 0.0664 (17) | −0.0101 (12) | 0.0222 (12) | −0.0003 (13) |
C4 | 0.0407 (13) | 0.0597 (16) | 0.0733 (18) | 0.0061 (12) | 0.0193 (13) | −0.0025 (13) |
C5 | 0.0411 (13) | 0.0434 (12) | 0.0550 (14) | 0.0039 (10) | 0.0081 (11) | 0.0017 (11) |
C6 | 0.0352 (11) | 0.0377 (11) | 0.0350 (11) | −0.0029 (9) | 0.0031 (9) | −0.0022 (9) |
C7 | 0.0400 (12) | 0.0414 (12) | 0.0405 (12) | −0.0012 (10) | 0.0054 (10) | −0.0034 (10) |
C8 | 0.0405 (12) | 0.0324 (10) | 0.0405 (12) | 0.0018 (9) | 0.0068 (9) | 0.0019 (9) |
C9 | 0.0391 (12) | 0.0369 (11) | 0.0355 (11) | −0.0003 (9) | 0.0057 (9) | −0.0014 (9) |
C10 | 0.0323 (11) | 0.0315 (10) | 0.0409 (11) | 0.0071 (9) | 0.0044 (9) | −0.0050 (9) |
C11 | 0.0277 (10) | 0.0282 (9) | 0.0384 (11) | −0.0023 (8) | −0.0018 (8) | −0.0061 (8) |
C12 | 0.0309 (10) | 0.0316 (10) | 0.0342 (10) | 0.0021 (8) | 0.0019 (8) | −0.0002 (8) |
C13 | 0.0335 (11) | 0.0417 (12) | 0.0406 (12) | 0.0010 (9) | −0.0009 (9) | 0.0101 (10) |
C14 | 0.0326 (13) | 0.0772 (18) | 0.0723 (18) | 0.0126 (12) | −0.0030 (12) | 0.0087 (15) |
C15 | 0.049 (3) | 0.071 (3) | 0.124 (8) | 0.005 (2) | −0.023 (5) | 0.025 (5) |
C15' | 0.049 (3) | 0.071 (3) | 0.124 (8) | 0.005 (2) | −0.023 (5) | 0.025 (5) |
C16 | 0.0287 (10) | 0.0337 (10) | 0.0333 (10) | 0.0029 (8) | 0.0017 (8) | 0.0002 (8) |
C17 | 0.0297 (11) | 0.0422 (12) | 0.0435 (12) | 0.0025 (9) | 0.0025 (9) | 0.0089 (10) |
C18 | 0.0301 (12) | 0.0647 (16) | 0.085 (2) | −0.0147 (11) | −0.0006 (12) | 0.0153 (15) |
C19 | 0.0648 (19) | 0.083 (2) | 0.095 (2) | −0.0328 (17) | −0.0254 (17) | 0.0057 (18) |
C20 | 0.0481 (13) | 0.0387 (11) | 0.0343 (11) | 0.0038 (10) | −0.0025 (10) | −0.0021 (9) |
C21 | 0.0410 (12) | 0.0308 (10) | 0.0366 (11) | 0.0016 (9) | −0.0065 (9) | 0.0013 (9) |
C22 | 0.0347 (11) | 0.0458 (12) | 0.0290 (10) | 0.0006 (9) | 0.0001 (9) | −0.0021 (9) |
C23 | 0.0498 (14) | 0.0517 (13) | 0.0433 (13) | −0.0055 (11) | −0.0019 (11) | −0.0088 (11) |
C24 | 0.0467 (14) | 0.0812 (19) | 0.0470 (14) | −0.0108 (13) | −0.0086 (11) | −0.0224 (14) |
C25 | 0.0401 (13) | 0.089 (2) | 0.0400 (13) | 0.0070 (13) | −0.0089 (10) | −0.0029 (13) |
C26 | 0.0364 (12) | 0.0676 (16) | 0.0410 (12) | 0.0061 (11) | 0.0006 (10) | 0.0076 (11) |
C27 | 0.0340 (11) | 0.0479 (12) | 0.0398 (12) | 0.0005 (10) | −0.0027 (9) | 0.0037 (10) |
C28 | 0.0587 (18) | 0.088 (2) | 0.091 (2) | 0.0069 (16) | −0.0165 (16) | 0.0415 (18) |
N1 | 0.0352 (9) | 0.0334 (9) | 0.0407 (10) | 0.0001 (7) | 0.0089 (8) | −0.0012 (8) |
N2 | 0.0324 (9) | 0.0301 (8) | 0.0349 (9) | 0.0022 (7) | 0.0049 (7) | −0.0001 (7) |
N3 | 0.0303 (9) | 0.0325 (8) | 0.0332 (9) | 0.0010 (7) | 0.0027 (7) | 0.0006 (7) |
N4 | 0.0381 (9) | 0.0319 (8) | 0.0330 (9) | 0.0031 (7) | 0.0011 (7) | −0.0012 (7) |
N5 | 0.0295 (8) | 0.0296 (8) | 0.0328 (9) | 0.0012 (7) | −0.0029 (7) | −0.0016 (7) |
N6 | 0.0422 (10) | 0.0325 (9) | 0.0344 (9) | 0.0030 (7) | −0.0079 (8) | −0.0035 (7) |
O1 | 0.0533 (10) | 0.0368 (8) | 0.0507 (9) | −0.0042 (7) | −0.0017 (8) | −0.0092 (7) |
O2 | 0.0359 (8) | 0.0403 (8) | 0.0505 (9) | 0.0094 (7) | 0.0026 (7) | −0.0070 (7) |
O3 | 0.0412 (9) | 0.0844 (12) | 0.0402 (9) | −0.0005 (8) | −0.0064 (7) | 0.0054 (9) |
O4 | 0.0344 (8) | 0.0740 (11) | 0.0546 (10) | 0.0209 (8) | −0.0046 (7) | −0.0056 (9) |
O5 | 0.0478 (10) | 0.0900 (14) | 0.0487 (10) | −0.0068 (9) | 0.0168 (8) | 0.0049 (9) |
O6 | 0.0317 (8) | 0.0581 (10) | 0.0544 (10) | −0.0146 (7) | 0.0027 (7) | −0.0002 (8) |
C1—C2 | 1.508 (3) | C15—H15A | 0.9600 |
C1—H1A | 0.9600 | C15—H15B | 0.9600 |
C1—H1B | 0.9600 | C15—H15C | 0.9600 |
C1—H1C | 0.9600 | C15'—H15D | 0.9600 |
C2—C3 | 1.377 (3) | C15'—H15E | 0.9600 |
C2—C7 | 1.395 (3) | C15'—H15F | 0.9600 |
C3—C4 | 1.376 (3) | C16—N4 | 1.448 (2) |
C3—H3 | 0.9300 | C16—N5 | 1.456 (2) |
C4—C5 | 1.374 (3) | C16—C17 | 1.538 (3) |
C4—H4 | 0.9300 | C17—O5 | 1.186 (3) |
C5—C6 | 1.393 (3) | C17—O6 | 1.323 (3) |
C5—H5 | 0.9300 | C18—O6 | 1.460 (3) |
C6—C7 | 1.391 (3) | C18—C19 | 1.481 (4) |
C6—N1 | 1.429 (2) | C18—H18A | 0.9700 |
C7—H7 | 0.9300 | C18—H18B | 0.9700 |
C8—N2 | 1.456 (2) | C19—H19A | 0.9600 |
C8—N1 | 1.462 (2) | C19—H19B | 0.9600 |
C8—H8A | 0.9700 | C19—H19C | 0.9600 |
C8—H8B | 0.9700 | C20—N4 | 1.455 (3) |
C9—N3 | 1.445 (2) | C20—N6 | 1.468 (3) |
C9—N1 | 1.470 (2) | C20—H20A | 0.9700 |
C9—H9A | 0.9700 | C20—H20B | 0.9700 |
C9—H9B | 0.9700 | C21—N5 | 1.453 (2) |
C10—O1 | 1.208 (2) | C21—N6 | 1.453 (2) |
C10—N2 | 1.378 (3) | C21—H21A | 0.9700 |
C10—N4 | 1.391 (3) | C21—H21B | 0.9700 |
C11—O2 | 1.211 (2) | C22—C27 | 1.385 (3) |
C11—N5 | 1.377 (2) | C22—C23 | 1.388 (3) |
C11—N3 | 1.384 (2) | C22—N6 | 1.423 (3) |
C12—N3 | 1.449 (2) | C23—C24 | 1.386 (3) |
C12—N2 | 1.455 (2) | C23—H23 | 0.9300 |
C12—C13 | 1.543 (3) | C24—C25 | 1.376 (4) |
C12—C16 | 1.565 (3) | C24—H24 | 0.9300 |
C13—O3 | 1.189 (3) | C25—C26 | 1.378 (3) |
C13—O4 | 1.327 (3) | C25—H25 | 0.9300 |
C14—C15' | 1.466 (12) | C26—C27 | 1.393 (3) |
C14—O4 | 1.472 (3) | C26—C28 | 1.500 (4) |
C14—C15 | 1.481 (7) | C27—H27 | 0.9300 |
C14—H14A | 0.9700 | C28—H28A | 0.9600 |
C14—H14B | 0.9700 | C28—H28B | 0.9600 |
C14—H14C | 0.9700 | C28—H28C | 0.9600 |
C14—H14D | 0.9700 | ||
C2—C1—H1A | 109.5 | N4—C16—N5 | 112.10 (15) |
C2—C1—H1B | 109.5 | N4—C16—C17 | 113.20 (16) |
H1A—C1—H1B | 109.5 | N5—C16—C17 | 108.43 (15) |
C2—C1—H1C | 109.5 | N4—C16—C12 | 103.70 (15) |
H1A—C1—H1C | 109.5 | N5—C16—C12 | 102.95 (14) |
H1B—C1—H1C | 109.5 | C17—C16—C12 | 116.04 (16) |
C3—C2—C7 | 118.8 (2) | O5—C17—O6 | 126.7 (2) |
C3—C2—C1 | 120.7 (2) | O5—C17—C16 | 125.2 (2) |
C7—C2—C1 | 120.5 (2) | O6—C17—C16 | 108.05 (17) |
C4—C3—C2 | 120.8 (2) | O6—C18—C19 | 106.8 (2) |
C4—C3—H3 | 119.6 | O6—C18—H18A | 110.4 |
C2—C3—H3 | 119.6 | C19—C18—H18A | 110.4 |
C5—C4—C3 | 120.5 (2) | O6—C18—H18B | 110.4 |
C5—C4—H4 | 119.7 | C19—C18—H18B | 110.4 |
C3—C4—H4 | 119.7 | H18A—C18—H18B | 108.6 |
C4—C5—C6 | 120.1 (2) | C18—C19—H19A | 109.5 |
C4—C5—H5 | 119.9 | C18—C19—H19B | 109.5 |
C6—C5—H5 | 119.9 | H19A—C19—H19B | 109.5 |
C7—C6—C5 | 118.83 (19) | C18—C19—H19C | 109.5 |
C7—C6—N1 | 123.38 (18) | H19A—C19—H19C | 109.5 |
C5—C6—N1 | 117.78 (18) | H19B—C19—H19C | 109.5 |
C6—C7—C2 | 120.9 (2) | N4—C20—N6 | 109.33 (16) |
C6—C7—H7 | 119.5 | N4—C20—H20A | 109.8 |
C2—C7—H7 | 119.5 | N6—C20—H20A | 109.8 |
N2—C8—N1 | 108.58 (15) | N4—C20—H20B | 109.8 |
N2—C8—H8A | 110.0 | N6—C20—H20B | 109.8 |
N1—C8—H8A | 110.0 | H20A—C20—H20B | 108.3 |
N2—C8—H8B | 110.0 | N5—C21—N6 | 108.40 (15) |
N1—C8—H8B | 110.0 | N5—C21—H21A | 110.0 |
H8A—C8—H8B | 108.4 | N6—C21—H21A | 110.0 |
N3—C9—N1 | 109.90 (16) | N5—C21—H21B | 110.0 |
N3—C9—H9A | 109.7 | N6—C21—H21B | 110.0 |
N1—C9—H9A | 109.7 | H21A—C21—H21B | 108.4 |
N3—C9—H9B | 109.7 | C27—C22—C23 | 119.1 (2) |
N1—C9—H9B | 109.7 | C27—C22—N6 | 122.10 (19) |
H9A—C9—H9B | 108.2 | C23—C22—N6 | 118.69 (19) |
O1—C10—N2 | 125.82 (19) | C24—C23—C22 | 119.7 (2) |
O1—C10—N4 | 125.72 (19) | C24—C23—H23 | 120.2 |
N2—C10—N4 | 108.38 (17) | C22—C23—H23 | 120.2 |
O2—C11—N5 | 126.11 (18) | C25—C24—C23 | 120.4 (2) |
O2—C11—N3 | 125.87 (19) | C25—C24—H24 | 119.8 |
N5—C11—N3 | 107.94 (16) | C23—C24—H24 | 119.8 |
N3—C12—N2 | 111.61 (15) | C24—C25—C26 | 121.1 (2) |
N3—C12—C13 | 111.51 (16) | C24—C25—H25 | 119.5 |
N2—C12—C13 | 110.57 (16) | C26—C25—H25 | 119.5 |
N3—C12—C16 | 103.62 (14) | C25—C26—C27 | 118.3 (2) |
N2—C12—C16 | 103.42 (15) | C25—C26—C28 | 121.8 (2) |
C13—C12—C16 | 115.71 (16) | C27—C26—C28 | 119.9 (2) |
O3—C13—O4 | 126.3 (2) | C22—C27—C26 | 121.4 (2) |
O3—C13—C12 | 124.1 (2) | C22—C27—H27 | 119.3 |
O4—C13—C12 | 109.68 (18) | C26—C27—H27 | 119.3 |
C15'—C14—O4 | 108.7 (8) | C26—C28—H28A | 109.5 |
O4—C14—C15 | 111.7 (4) | C26—C28—H28B | 109.5 |
C15'—C14—H14A | 132.4 | H28A—C28—H28B | 109.5 |
O4—C14—H14A | 109.3 | C26—C28—H28C | 109.5 |
C15—C14—H14A | 109.3 | H28A—C28—H28C | 109.5 |
C15'—C14—H14B | 85.1 | H28B—C28—H28C | 109.5 |
O4—C14—H14B | 109.3 | C6—N1—C8 | 117.50 (16) |
C15—C14—H14B | 109.3 | C6—N1—C9 | 113.46 (15) |
H14A—C14—H14B | 107.9 | C8—N1—C9 | 109.62 (16) |
C15'—C14—H14C | 110.1 | C10—N2—C12 | 110.98 (15) |
O4—C14—H14C | 109.7 | C10—N2—C8 | 120.71 (17) |
C15—C14—H14C | 129.4 | C12—N2—C8 | 117.09 (15) |
H14A—C14—H14C | 82.5 | C11—N3—C9 | 118.69 (16) |
C15'—C14—H14D | 109.7 | C11—N3—C12 | 110.95 (15) |
O4—C14—H14D | 110.2 | C9—N3—C12 | 116.54 (15) |
C15—C14—H14D | 83.1 | C10—N4—C16 | 110.48 (15) |
H14B—C14—H14D | 129.8 | C10—N4—C20 | 118.04 (17) |
H14C—C14—H14D | 108.3 | C16—N4—C20 | 116.66 (15) |
C14—C15—H15A | 109.5 | C11—N5—C21 | 120.77 (16) |
C14—C15—H15B | 109.5 | C11—N5—C16 | 111.50 (15) |
C14—C15—H15C | 109.5 | C21—N5—C16 | 116.32 (15) |
C14—C15'—H15D | 109.5 | C22—N6—C21 | 116.54 (16) |
C14—C15'—H15E | 109.5 | C22—N6—C20 | 115.66 (16) |
H15D—C15'—H15E | 109.5 | C21—N6—C20 | 109.98 (16) |
C14—C15'—H15F | 109.5 | C13—O4—C14 | 116.89 (19) |
H15D—C15'—H15F | 109.5 | C17—O6—C18 | 118.24 (18) |
H15E—C15'—H15F | 109.5 | ||
C7—C2—C3—C4 | 0.6 (4) | N3—C12—N2—C8 | −42.0 (2) |
C1—C2—C3—C4 | 179.8 (3) | C13—C12—N2—C8 | 82.7 (2) |
C2—C3—C4—C5 | −0.1 (4) | C16—C12—N2—C8 | −152.79 (16) |
C3—C4—C5—C6 | −0.4 (4) | N1—C8—N2—C10 | −88.0 (2) |
C4—C5—C6—C7 | 0.2 (3) | N1—C8—N2—C12 | 52.4 (2) |
C4—C5—C6—N1 | 179.1 (2) | O2—C11—N3—C9 | 26.0 (3) |
C5—C6—C7—C2 | 0.4 (3) | N5—C11—N3—C9 | −157.13 (16) |
N1—C6—C7—C2 | −178.43 (19) | O2—C11—N3—C12 | 165.04 (18) |
C3—C2—C7—C6 | −0.8 (3) | N5—C11—N3—C12 | −18.1 (2) |
C1—C2—C7—C6 | −180.0 (2) | N1—C9—N3—C11 | 85.2 (2) |
N3—C12—C13—O3 | 6.8 (3) | N1—C9—N3—C12 | −51.6 (2) |
N2—C12—C13—O3 | −118.0 (2) | N2—C12—N3—C11 | −98.72 (18) |
C16—C12—C13—O3 | 124.9 (2) | C13—C12—N3—C11 | 137.07 (16) |
N3—C12—C13—O4 | −173.02 (16) | C16—C12—N3—C11 | 11.95 (19) |
N2—C12—C13—O4 | 62.2 (2) | N2—C12—N3—C9 | 41.3 (2) |
C16—C12—C13—O4 | −54.9 (2) | C13—C12—N3—C9 | −83.0 (2) |
N3—C12—C16—N4 | −118.72 (15) | C16—C12—N3—C9 | 151.93 (16) |
N2—C12—C16—N4 | −2.15 (18) | O1—C10—N4—C16 | 164.86 (19) |
C13—C12—C16—N4 | 118.91 (18) | N2—C10—N4—C16 | −18.2 (2) |
N3—C12—C16—N5 | −1.75 (18) | O1—C10—N4—C20 | 27.0 (3) |
N2—C12—C16—N5 | 114.82 (15) | N2—C10—N4—C20 | −156.09 (16) |
C13—C12—C16—N5 | −124.13 (17) | N5—C16—N4—C10 | −98.17 (18) |
N3—C12—C16—C17 | 116.50 (18) | C17—C16—N4—C10 | 138.78 (17) |
N2—C12—C16—C17 | −126.92 (17) | C12—C16—N4—C10 | 12.19 (19) |
C13—C12—C16—C17 | −5.9 (2) | N5—C16—N4—C20 | 40.3 (2) |
N4—C16—C17—O5 | 12.0 (3) | C17—C16—N4—C20 | −82.7 (2) |
N5—C16—C17—O5 | −113.0 (2) | C12—C16—N4—C20 | 150.68 (16) |
C12—C16—C17—O5 | 131.8 (2) | N6—C20—N4—C10 | 85.2 (2) |
N4—C16—C17—O6 | −170.98 (16) | N6—C20—N4—C16 | −50.1 (2) |
N5—C16—C17—O6 | 64.0 (2) | O2—C11—N5—C21 | −24.1 (3) |
C12—C16—C17—O6 | −51.2 (2) | N3—C11—N5—C21 | 159.02 (15) |
C27—C22—C23—C24 | −1.0 (3) | O2—C11—N5—C16 | −166.26 (18) |
N6—C22—C23—C24 | 176.1 (2) | N3—C11—N5—C16 | 16.9 (2) |
C22—C23—C24—C25 | 1.4 (4) | N6—C21—N5—C11 | −86.8 (2) |
C23—C24—C25—C26 | −1.1 (4) | N6—C21—N5—C16 | 53.6 (2) |
C24—C25—C26—C27 | 0.3 (4) | N4—C16—N5—C11 | 101.83 (18) |
C24—C25—C26—C28 | 179.5 (3) | C17—C16—N5—C11 | −132.47 (17) |
C23—C22—C27—C26 | 0.2 (3) | C12—C16—N5—C11 | −9.00 (19) |
N6—C22—C27—C26 | −176.70 (19) | N4—C16—N5—C21 | −42.1 (2) |
C25—C26—C27—C22 | 0.1 (3) | C17—C16—N5—C21 | 83.6 (2) |
C28—C26—C27—C22 | −179.1 (2) | C12—C16—N5—C21 | −152.95 (16) |
C7—C6—N1—C8 | 11.7 (3) | C27—C22—N6—C21 | 13.4 (3) |
C5—C6—N1—C8 | −167.11 (19) | C23—C22—N6—C21 | −163.54 (19) |
C7—C6—N1—C9 | −118.0 (2) | C27—C22—N6—C20 | −118.2 (2) |
C5—C6—N1—C9 | 63.2 (2) | C23—C22—N6—C20 | 64.9 (2) |
N2—C8—N1—C6 | 168.14 (16) | N5—C21—N6—C22 | 163.66 (16) |
N2—C8—N1—C9 | −60.4 (2) | N5—C21—N6—C20 | −62.2 (2) |
N3—C9—N1—C6 | −165.72 (16) | N4—C20—N6—C22 | −164.63 (17) |
N3—C9—N1—C8 | 60.7 (2) | N4—C20—N6—C21 | 60.8 (2) |
O1—C10—N2—C12 | −166.38 (19) | O3—C13—O4—C14 | −5.7 (3) |
N4—C10—N2—C12 | 16.7 (2) | C12—C13—O4—C14 | 174.17 (18) |
O1—C10—N2—C8 | −23.7 (3) | C15'—C14—O4—C13 | 116.8 (10) |
N4—C10—N2—C8 | 159.39 (16) | C15—C14—O4—C13 | 87.0 (8) |
N3—C12—N2—C10 | 102.14 (18) | O5—C17—O6—C18 | −5.5 (3) |
C13—C12—N2—C10 | −133.11 (17) | C16—C17—O6—C18 | 177.54 (18) |
C16—C12—N2—C10 | −8.64 (19) | C19—C18—O6—C17 | −177.4 (2) |
Experimental details
Crystal data | |
Chemical formula | C28H32N6O6 |
Mr | 548.60 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 292 |
a, b, c (Å) | 17.8591 (13), 15.4533 (11), 19.5649 (14) |
V (Å3) | 5399.6 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30333, 5874, 4406 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.136, 1.05 |
No. of reflections | 5874 |
No. of parameters | 370 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
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Since Mock and co-workers first characterized the chemical nature and structure of cucurbit[6]uril (Freeman et al., 1981), many clip molecules based on glycoluril as supramolecular receptor have been reported (Rowan et al., 1999; Li et al., 2006; Wang et al., 2006; Chen et al., 2007; Hu et al., 2007; She et al., 2007). As a continuation of our previous studies in this area, we herein report the crystal structure of the title compound, (I), a new type of receptor based on glycoluril (Fig. 1). Selected bond lengths and angles are listed in Table 1. Two six-membered rings (N1—C8—N2 –C12—N3—C9 and N4—C16—N5—C21—N6—C20) both adopt the chair conformation. The dihedral angle between the two fused five-membered rings in the glycoluril unit is 71.78 (2) °. The crystal packing is mainly governed by van der Waals forces.