Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058400/lw2043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058400/lw2043Isup2.hkl |
CCDC reference: 672991
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.060
- wR factor = 0.164
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.105 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the preparation of the title compound, see: Li et al. (2006). For related literature, see: Degen et al., (2007); Elemans et al. (2000); Freeman et al. (1981); Klarner & Kahlert (2003); Rebek (2005); Rowan et al. (1999); Wu et al. (2002).
The title compound was synthesized according to the procedure of Li, et al. (2006) in 12% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methanol solution in ratio of 15:1 at 293 K.
All H atoms were positioned geometrically (C—H = 0.96–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) (1.5Ueq(C) for methyl of the parent atoms.
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. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 10% probability level. H atoms are represented by spheres of arbitrary radius. |
C24H28N6O2 | Z = 2 |
Mr = 432.52 | F(000) = 460 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6963 (9) Å | Cell parameters from 1908 reflections |
b = 10.3704 (10) Å | θ = 2.3–23.7° |
c = 13.0294 (13) Å | µ = 0.09 mm−1 |
α = 76.885 (2)° | T = 295 K |
β = 73.233 (1)° | Block, blue |
γ = 84.576 (1)° | 0.20 × 0.20 × 0.10 mm |
V = 1095.21 (19) Å3 |
Bruker SMART 4K CCD area-detector diffractometer | 2885 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.105 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ϕ and ω scans | h = −10→10 |
7080 measured reflections | k = −12→11 |
4255 independent reflections | l = −16→16 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3 |
4255 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C24H28N6O2 | γ = 84.576 (1)° |
Mr = 432.52 | V = 1095.21 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6963 (9) Å | Mo Kα radiation |
b = 10.3704 (10) Å | µ = 0.09 mm−1 |
c = 13.0294 (13) Å | T = 295 K |
α = 76.885 (2)° | 0.20 × 0.20 × 0.10 mm |
β = 73.233 (1)° |
Bruker SMART 4K CCD area-detector diffractometer | 2885 reflections with I > 2σ(I) |
7080 measured reflections | Rint = 0.105 |
4255 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.25 e Å−3 |
4255 reflections | Δρmin = −0.23 e Å−3 |
291 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 | ||
C1 | 0.0890 (4) | −0.2902 (3) | 0.9644 (2) | 0.0645 (8) | |
H1A | 0.1391 | −0.2709 | 1.0157 | 0.097* | |
H1B | 0.0987 | −0.3835 | 0.9661 | 0.097* | |
H1C | −0.0226 | −0.2635 | 0.9839 | 0.097* | |
C2 | 0.1698 (3) | −0.2160 (2) | 0.8515 (2) | 0.0457 (6) | |
H2A | 0.2850 | −0.2313 | 0.8377 | 0.055* | |
H2B | 0.1362 | −0.2511 | 0.7986 | 0.055* | |
C3 | 0.1908 (3) | −0.0040 (2) | 0.90159 (19) | 0.0391 (6) | |
H3A | 0.1646 | −0.0551 | 0.9763 | 0.047* | |
H3B | 0.1337 | 0.0809 | 0.9023 | 0.047* | |
C4 | 0.1900 (3) | −0.0064 (2) | 0.71965 (19) | 0.0393 (6) | |
H4A | 0.1325 | 0.0783 | 0.7091 | 0.047* | |
H4B | 0.1638 | −0.0592 | 0.6748 | 0.047* | |
C5 | 0.4739 (3) | −0.0717 (2) | 0.89922 (18) | 0.0328 (5) | |
C6 | 0.4730 (3) | −0.0729 (2) | 0.63566 (17) | 0.0305 (5) | |
C7 | 0.4254 (2) | 0.0817 (2) | 0.74911 (16) | 0.0283 (5) | |
C8 | 0.3877 (2) | 0.2307 (2) | 0.72892 (17) | 0.0299 (5) | |
C9 | 0.3722 (3) | 0.2996 (2) | 0.8109 (2) | 0.0437 (6) | |
H9 | 0.3805 | 0.2550 | 0.8797 | 0.052* | |
C10 | 0.3441 (4) | 0.4357 (3) | 0.7899 (2) | 0.0599 (8) | |
H10 | 0.3345 | 0.4822 | 0.8447 | 0.072* | |
C11 | 0.3304 (3) | 0.5026 (3) | 0.6891 (3) | 0.0574 (8) | |
H11 | 0.3105 | 0.5937 | 0.6760 | 0.069* | |
C12 | 0.3462 (3) | 0.4342 (3) | 0.6077 (2) | 0.0492 (7) | |
H12 | 0.3373 | 0.4794 | 0.5392 | 0.059* | |
C13 | 0.3753 (3) | 0.2983 (2) | 0.62682 (19) | 0.0385 (6) | |
H13 | 0.3866 | 0.2526 | 0.5712 | 0.046* | |
C14 | 0.6075 (2) | 0.0377 (2) | 0.72159 (16) | 0.0279 (5) | |
C15 | 0.7302 (2) | 0.1463 (2) | 0.67807 (18) | 0.0314 (5) | |
C16 | 0.7865 (3) | 0.1967 (2) | 0.7500 (2) | 0.0418 (6) | |
H16 | 0.7484 | 0.1649 | 0.8252 | 0.050* | |
C17 | 0.8994 (3) | 0.2942 (3) | 0.7098 (2) | 0.0519 (7) | |
H17 | 0.9373 | 0.3277 | 0.7580 | 0.062* | |
C18 | 0.9557 (3) | 0.3416 (3) | 0.5991 (2) | 0.0536 (7) | |
H18 | 1.0326 | 0.4064 | 0.5724 | 0.064* | |
C19 | 0.8986 (3) | 0.2936 (3) | 0.5272 (2) | 0.0495 (7) | |
H19 | 0.9360 | 0.3267 | 0.4521 | 0.059* | |
C20 | 0.7859 (3) | 0.1962 (2) | 0.56666 (19) | 0.0404 (6) | |
H20 | 0.7472 | 0.1641 | 0.5181 | 0.048* | |
C21 | 0.7575 (3) | −0.1426 (3) | 0.8167 (2) | 0.0436 (6) | |
H21A | 0.8566 | −0.0956 | 0.7969 | 0.052* | |
H21B | 0.7471 | −0.2001 | 0.8882 | 0.052* | |
C22 | 0.7572 (3) | −0.1410 (2) | 0.6332 (2) | 0.0455 (6) | |
H22A | 0.7485 | −0.1976 | 0.5853 | 0.055* | |
H22B | 0.8559 | −0.0931 | 0.5989 | 0.055* | |
C23 | 0.6583 (4) | −0.3353 (3) | 0.7767 (2) | 0.0571 (7) | |
H23A | 0.6630 | −0.3773 | 0.7165 | 0.068* | |
H23B | 0.5492 | −0.3016 | 0.8023 | 0.068* | |
C24 | 0.6991 (5) | −0.4366 (3) | 0.8681 (3) | 0.0896 (12) | |
H24A | 0.8115 | −0.4602 | 0.8471 | 0.134* | |
H24B | 0.6372 | −0.5139 | 0.8828 | 0.134* | |
H24C | 0.6745 | −0.4003 | 0.9327 | 0.134* | |
N1 | 0.1345 (2) | −0.07304 (19) | 0.83424 (16) | 0.0393 (5) | |
N2 | 0.3631 (2) | 0.01826 (17) | 0.86419 (14) | 0.0304 (4) | |
N3 | 0.3625 (2) | 0.01628 (17) | 0.68186 (14) | 0.0303 (4) | |
N4 | 0.6222 (2) | −0.04582 (18) | 0.82483 (14) | 0.0316 (4) | |
N5 | 0.6212 (2) | −0.04532 (18) | 0.64235 (14) | 0.0323 (4) | |
N6 | 0.7685 (2) | −0.2239 (2) | 0.73700 (17) | 0.0449 (5) | |
O1 | 0.4475 (2) | −0.15622 (16) | 0.98420 (12) | 0.0451 (5) | |
O2 | 0.4458 (2) | −0.15742 (16) | 0.59266 (12) | 0.0425 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.061 (2) | 0.0429 (16) | 0.078 (2) | −0.0049 (14) | −0.0077 (16) | −0.0041 (15) |
C2 | 0.0360 (14) | 0.0336 (14) | 0.0638 (17) | −0.0038 (11) | −0.0060 (12) | −0.0119 (12) |
C3 | 0.0284 (13) | 0.0375 (13) | 0.0457 (14) | −0.0013 (10) | 0.0016 (10) | −0.0125 (11) |
C4 | 0.0277 (13) | 0.0391 (14) | 0.0544 (15) | −0.0013 (11) | −0.0134 (11) | −0.0134 (12) |
C5 | 0.0341 (13) | 0.0350 (13) | 0.0306 (12) | −0.0086 (10) | −0.0067 (10) | −0.0092 (10) |
C6 | 0.0332 (13) | 0.0301 (12) | 0.0289 (12) | −0.0025 (10) | −0.0069 (10) | −0.0090 (10) |
C7 | 0.0263 (11) | 0.0292 (12) | 0.0288 (11) | −0.0020 (9) | −0.0036 (9) | −0.0097 (9) |
C8 | 0.0221 (11) | 0.0277 (12) | 0.0385 (13) | −0.0017 (9) | −0.0044 (9) | −0.0087 (10) |
C9 | 0.0537 (16) | 0.0340 (13) | 0.0438 (14) | −0.0018 (12) | −0.0093 (12) | −0.0142 (11) |
C10 | 0.082 (2) | 0.0369 (15) | 0.0650 (19) | 0.0007 (15) | −0.0156 (17) | −0.0256 (14) |
C11 | 0.0582 (19) | 0.0290 (14) | 0.082 (2) | 0.0036 (13) | −0.0156 (16) | −0.0132 (15) |
C12 | 0.0477 (16) | 0.0362 (14) | 0.0576 (17) | −0.0016 (12) | −0.0143 (13) | 0.0022 (12) |
C13 | 0.0370 (14) | 0.0333 (13) | 0.0438 (14) | −0.0005 (11) | −0.0081 (11) | −0.0093 (11) |
C14 | 0.0219 (11) | 0.0313 (12) | 0.0301 (11) | −0.0021 (9) | −0.0039 (9) | −0.0093 (9) |
C15 | 0.0218 (11) | 0.0306 (12) | 0.0393 (13) | 0.0002 (9) | −0.0041 (9) | −0.0081 (10) |
C16 | 0.0388 (14) | 0.0419 (14) | 0.0444 (14) | −0.0075 (11) | −0.0085 (11) | −0.0095 (11) |
C17 | 0.0467 (16) | 0.0436 (16) | 0.0706 (19) | −0.0145 (13) | −0.0218 (14) | −0.0098 (14) |
C18 | 0.0341 (15) | 0.0373 (14) | 0.082 (2) | −0.0126 (12) | −0.0143 (14) | 0.0053 (14) |
C19 | 0.0358 (14) | 0.0463 (15) | 0.0527 (16) | −0.0070 (12) | −0.0007 (12) | 0.0046 (13) |
C20 | 0.0354 (14) | 0.0414 (14) | 0.0401 (14) | −0.0058 (11) | −0.0043 (11) | −0.0059 (11) |
C21 | 0.0295 (13) | 0.0438 (15) | 0.0566 (16) | 0.0015 (11) | −0.0146 (12) | −0.0058 (12) |
C22 | 0.0357 (14) | 0.0437 (15) | 0.0538 (16) | 0.0073 (12) | −0.0015 (12) | −0.0214 (13) |
C23 | 0.0547 (18) | 0.0364 (15) | 0.080 (2) | 0.0035 (13) | −0.0194 (15) | −0.0142 (14) |
C24 | 0.112 (3) | 0.0472 (19) | 0.108 (3) | −0.005 (2) | −0.039 (2) | 0.0013 (19) |
N1 | 0.0267 (10) | 0.0334 (11) | 0.0545 (13) | −0.0037 (9) | −0.0057 (9) | −0.0086 (9) |
N2 | 0.0253 (10) | 0.0320 (10) | 0.0300 (10) | −0.0041 (8) | 0.0005 (8) | −0.0078 (8) |
N3 | 0.0256 (10) | 0.0302 (10) | 0.0369 (10) | −0.0012 (8) | −0.0074 (8) | −0.0118 (8) |
N4 | 0.0255 (10) | 0.0324 (10) | 0.0352 (10) | −0.0023 (8) | −0.0066 (8) | −0.0051 (8) |
N5 | 0.0282 (10) | 0.0330 (10) | 0.0342 (10) | 0.0028 (8) | −0.0027 (8) | −0.0136 (8) |
N6 | 0.0329 (12) | 0.0394 (12) | 0.0598 (14) | 0.0054 (9) | −0.0105 (10) | −0.0110 (10) |
O1 | 0.0485 (11) | 0.0458 (10) | 0.0347 (9) | −0.0089 (8) | −0.0067 (8) | 0.0011 (8) |
O2 | 0.0494 (11) | 0.0406 (9) | 0.0439 (10) | −0.0024 (8) | −0.0132 (8) | −0.0206 (8) |
C1—C2 | 1.497 (3) | C12—C13 | 1.387 (3) |
C1—H1A | 0.9600 | C12—H12 | 0.9300 |
C1—H1B | 0.9600 | C13—H13 | 0.9300 |
C1—H1C | 0.9600 | C14—N4 | 1.458 (3) |
C2—N1 | 1.465 (3) | C14—N5 | 1.461 (3) |
C2—H2A | 0.9700 | C14—C15 | 1.522 (3) |
C2—H2B | 0.9700 | C15—C20 | 1.382 (3) |
C3—N1 | 1.457 (3) | C15—C16 | 1.388 (3) |
C3—N2 | 1.459 (3) | C16—C17 | 1.382 (3) |
C3—H3A | 0.9700 | C16—H16 | 0.9300 |
C3—H3B | 0.9700 | C17—C18 | 1.370 (4) |
C4—N1 | 1.456 (3) | C17—H17 | 0.9300 |
C4—N3 | 1.461 (3) | C18—C19 | 1.378 (4) |
C4—H4A | 0.9700 | C18—H18 | 0.9300 |
C4—H4B | 0.9700 | C19—C20 | 1.380 (3) |
C5—O1 | 1.224 (2) | C19—H19 | 0.9300 |
C5—N2 | 1.377 (3) | C20—H20 | 0.9300 |
C5—N4 | 1.379 (3) | C21—N6 | 1.458 (3) |
C6—O2 | 1.216 (2) | C21—N4 | 1.468 (3) |
C6—N3 | 1.375 (3) | C21—H21A | 0.9700 |
C6—N5 | 1.377 (3) | C21—H21B | 0.9700 |
C7—N2 | 1.458 (3) | C22—N6 | 1.453 (3) |
C7—N3 | 1.464 (2) | C22—N5 | 1.466 (3) |
C7—C8 | 1.528 (3) | C22—H22A | 0.9700 |
C7—C14 | 1.566 (3) | C22—H22B | 0.9700 |
C8—C9 | 1.384 (3) | C23—N6 | 1.474 (3) |
C8—C13 | 1.385 (3) | C23—C24 | 1.500 (4) |
C9—C10 | 1.387 (4) | C23—H23A | 0.9700 |
C9—H9 | 0.9300 | C23—H23B | 0.9700 |
C10—C11 | 1.371 (4) | C24—H24A | 0.9600 |
C10—H10 | 0.9300 | C24—H24B | 0.9600 |
C11—C12 | 1.373 (4) | C24—H24C | 0.9600 |
C11—H11 | 0.9300 | ||
C2—C1—H1A | 109.5 | C20—C15—C16 | 119.4 (2) |
C2—C1—H1B | 109.5 | C20—C15—C14 | 120.36 (19) |
H1A—C1—H1B | 109.5 | C16—C15—C14 | 120.3 (2) |
C2—C1—H1C | 109.5 | C17—C16—C15 | 119.9 (2) |
H1A—C1—H1C | 109.5 | C17—C16—H16 | 120.0 |
H1B—C1—H1C | 109.5 | C15—C16—H16 | 120.0 |
N1—C2—C1 | 113.7 (2) | C18—C17—C16 | 120.3 (2) |
N1—C2—H2A | 108.8 | C18—C17—H17 | 119.9 |
C1—C2—H2A | 108.8 | C16—C17—H17 | 119.9 |
N1—C2—H2B | 108.8 | C17—C18—C19 | 120.2 (2) |
C1—C2—H2B | 108.8 | C17—C18—H18 | 119.9 |
H2A—C2—H2B | 107.7 | C19—C18—H18 | 119.9 |
N1—C3—N2 | 113.90 (18) | C18—C19—C20 | 119.9 (2) |
N1—C3—H3A | 108.8 | C18—C19—H19 | 120.0 |
N2—C3—H3A | 108.8 | C20—C19—H19 | 120.0 |
N1—C3—H3B | 108.8 | C19—C20—C15 | 120.3 (2) |
N2—C3—H3B | 108.8 | C19—C20—H20 | 119.8 |
H3A—C3—H3B | 107.7 | C15—C20—H20 | 119.8 |
N1—C4—N3 | 113.84 (18) | N6—C21—N4 | 113.91 (18) |
N1—C4—H4A | 108.8 | N6—C21—H21A | 108.8 |
N3—C4—H4A | 108.8 | N4—C21—H21A | 108.8 |
N1—C4—H4B | 108.8 | N6—C21—H21B | 108.8 |
N3—C4—H4B | 108.8 | N4—C21—H21B | 108.8 |
H4A—C4—H4B | 107.7 | H21A—C21—H21B | 107.7 |
O1—C5—N2 | 126.2 (2) | N6—C22—N5 | 114.39 (19) |
O1—C5—N4 | 125.5 (2) | N6—C22—H22A | 108.7 |
N2—C5—N4 | 108.24 (18) | N5—C22—H22A | 108.7 |
O2—C6—N3 | 126.1 (2) | N6—C22—H22B | 108.7 |
O2—C6—N5 | 126.1 (2) | N5—C22—H22B | 108.7 |
N3—C6—N5 | 107.80 (17) | H22A—C22—H22B | 107.6 |
N2—C7—N3 | 109.20 (15) | N6—C23—C24 | 112.2 (2) |
N2—C7—C8 | 111.82 (17) | N6—C23—H23A | 109.2 |
N3—C7—C8 | 112.05 (17) | C24—C23—H23A | 109.2 |
N2—C7—C14 | 103.45 (16) | N6—C23—H23B | 109.2 |
N3—C7—C14 | 103.08 (16) | C24—C23—H23B | 109.2 |
C8—C7—C14 | 116.52 (16) | H23A—C23—H23B | 107.9 |
C9—C8—C13 | 119.7 (2) | C23—C24—H24A | 109.5 |
C9—C8—C7 | 120.3 (2) | C23—C24—H24B | 109.5 |
C13—C8—C7 | 119.94 (19) | H24A—C24—H24B | 109.5 |
C8—C9—C10 | 119.5 (2) | C23—C24—H24C | 109.5 |
C8—C9—H9 | 120.2 | H24A—C24—H24C | 109.5 |
C10—C9—H9 | 120.2 | H24B—C24—H24C | 109.5 |
C11—C10—C9 | 120.8 (2) | C4—N1—C3 | 109.47 (17) |
C11—C10—H10 | 119.6 | C4—N1—C2 | 112.71 (19) |
C9—C10—H10 | 119.6 | C3—N1—C2 | 115.28 (19) |
C10—C11—C12 | 119.6 (2) | C5—N2—C7 | 111.13 (17) |
C10—C11—H11 | 120.2 | C5—N2—C3 | 122.64 (18) |
C12—C11—H11 | 120.2 | C7—N2—C3 | 115.74 (17) |
C11—C12—C13 | 120.5 (2) | C6—N3—C4 | 122.70 (18) |
C11—C12—H12 | 119.8 | C6—N3—C7 | 111.66 (17) |
C13—C12—H12 | 119.8 | C4—N3—C7 | 115.74 (17) |
C8—C13—C12 | 119.8 (2) | C5—N4—C14 | 111.48 (18) |
C8—C13—H13 | 120.1 | C5—N4—C21 | 123.05 (19) |
C12—C13—H13 | 120.1 | C14—N4—C21 | 115.96 (18) |
N4—C14—N5 | 109.15 (17) | C6—N5—C14 | 111.84 (17) |
N4—C14—C15 | 111.90 (16) | C6—N5—C22 | 123.01 (19) |
N5—C14—C15 | 111.68 (17) | C14—N5—C22 | 115.18 (17) |
N4—C14—C7 | 102.98 (15) | C22—N6—C21 | 110.28 (18) |
N5—C14—C7 | 102.89 (15) | C22—N6—C23 | 113.4 (2) |
C15—C14—C7 | 117.46 (18) | C21—N6—C23 | 114.3 (2) |
N2—C7—C8—C9 | 29.1 (3) | C14—C7—N2—C5 | −10.5 (2) |
N3—C7—C8—C9 | 152.1 (2) | N3—C7—N2—C3 | −47.2 (2) |
C14—C7—C8—C9 | −89.6 (2) | C8—C7—N2—C3 | 77.4 (2) |
N2—C7—C8—C13 | −153.51 (19) | C14—C7—N2—C3 | −156.44 (17) |
N3—C7—C8—C13 | −30.5 (3) | N1—C3—N2—C5 | −89.5 (2) |
C14—C7—C8—C13 | 87.8 (2) | N1—C3—N2—C7 | 52.2 (3) |
C13—C8—C9—C10 | 0.1 (4) | O2—C6—N3—C4 | 22.0 (3) |
C7—C8—C9—C10 | 177.5 (2) | N5—C6—N3—C4 | −160.69 (18) |
C8—C9—C10—C11 | 0.5 (4) | O2—C6—N3—C7 | 166.1 (2) |
C9—C10—C11—C12 | −0.6 (4) | N5—C6—N3—C7 | −16.6 (2) |
C10—C11—C12—C13 | 0.2 (4) | N1—C4—N3—C6 | 91.0 (2) |
C9—C8—C13—C12 | −0.5 (3) | N1—C4—N3—C7 | −51.7 (3) |
C7—C8—C13—C12 | −177.9 (2) | N2—C7—N3—C6 | −99.8 (2) |
C11—C12—C13—C8 | 0.4 (4) | C8—C7—N3—C6 | 135.78 (19) |
N2—C7—C14—N4 | 0.65 (18) | C14—C7—N3—C6 | 9.7 (2) |
N3—C7—C14—N4 | −113.10 (16) | N2—C7—N3—C4 | 47.0 (2) |
C8—C7—C14—N4 | 123.77 (18) | C8—C7—N3—C4 | −77.4 (2) |
N2—C7—C14—N5 | 114.10 (16) | C14—C7—N3—C4 | 156.51 (17) |
N3—C7—C14—N5 | 0.36 (19) | O1—C5—N4—C14 | 166.56 (19) |
C8—C7—C14—N5 | −122.78 (18) | N2—C5—N4—C14 | −16.5 (2) |
N2—C7—C14—C15 | −122.80 (18) | O1—C5—N4—C21 | 21.7 (3) |
N3—C7—C14—C15 | 123.45 (18) | N2—C5—N4—C21 | −161.32 (18) |
C8—C7—C14—C15 | 0.3 (3) | N5—C14—N4—C5 | −99.4 (2) |
N4—C14—C15—C20 | 151.3 (2) | C15—C14—N4—C5 | 136.47 (19) |
N5—C14—C15—C20 | 28.6 (3) | C7—C14—N4—C5 | 9.4 (2) |
C7—C14—C15—C20 | −89.9 (3) | N5—C14—N4—C21 | 48.1 (2) |
N4—C14—C15—C16 | −29.1 (3) | C15—C14—N4—C21 | −76.0 (2) |
N5—C14—C15—C16 | −151.8 (2) | C7—C14—N4—C21 | 156.92 (17) |
C7—C14—C15—C16 | 89.7 (2) | N6—C21—N4—C5 | 92.6 (3) |
C20—C15—C16—C17 | −1.1 (4) | N6—C21—N4—C14 | −50.8 (3) |
C14—C15—C16—C17 | 179.2 (2) | O2—C6—N5—C14 | −165.8 (2) |
C15—C16—C17—C18 | 0.1 (4) | N3—C6—N5—C14 | 16.9 (2) |
C16—C17—C18—C19 | 0.8 (4) | O2—C6—N5—C22 | −22.0 (3) |
C17—C18—C19—C20 | −0.8 (4) | N3—C6—N5—C22 | 160.70 (19) |
C18—C19—C20—C15 | −0.2 (4) | N4—C14—N5—C6 | 98.52 (19) |
C16—C15—C20—C19 | 1.1 (4) | C15—C14—N5—C6 | −137.22 (19) |
C14—C15—C20—C19 | −179.2 (2) | C7—C14—N5—C6 | −10.3 (2) |
N3—C4—N1—C3 | 51.3 (2) | N4—C14—N5—C22 | −48.3 (2) |
N3—C4—N1—C2 | −78.4 (2) | C15—C14—N5—C22 | 76.0 (2) |
N2—C3—N1—C4 | −51.5 (2) | C7—C14—N5—C22 | −157.17 (17) |
N2—C3—N1—C2 | 76.7 (3) | N6—C22—N5—C6 | −90.8 (2) |
C1—C2—N1—C4 | −169.8 (2) | N6—C22—N5—C14 | 51.9 (3) |
C1—C2—N1—C3 | 63.6 (3) | N5—C22—N6—C21 | −49.9 (3) |
O1—C5—N2—C7 | −166.2 (2) | N5—C22—N6—C23 | 79.8 (3) |
N4—C5—N2—C7 | 16.9 (2) | N4—C21—N6—C22 | 49.0 (3) |
O1—C5—N2—C3 | −23.0 (3) | N4—C21—N6—C23 | −80.2 (3) |
N4—C5—N2—C3 | 160.07 (18) | C24—C23—N6—C22 | 166.3 (3) |
N3—C7—N2—C5 | 98.73 (19) | C24—C23—N6—C21 | −66.1 (3) |
C8—C7—N2—C5 | −136.70 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1i | 0.93 | 2.56 | 3.427 (3) | 155 |
C13—H13···O2ii | 0.93 | 2.56 | 3.410 (3) | 152 |
C20—H20···O2ii | 0.93 | 2.52 | 3.387 (3) | 155 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C24H28N6O2 |
Mr | 432.52 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.6963 (9), 10.3704 (10), 13.0294 (13) |
α, β, γ (°) | 76.885 (2), 73.233 (1), 84.576 (1) |
V (Å3) | 1095.21 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 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 | 7080, 4255, 2885 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.164, 0.99 |
No. of reflections | 4255 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.23 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON (Spek, 2003.
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1i | 0.93 | 2.56 | 3.427 (3) | 154.9 |
C13—H13···O2ii | 0.93 | 2.56 | 3.410 (3) | 152.4 |
C20—H20···O2ii | 0.93 | 2.52 | 3.387 (3) | 154.7 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1. |
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Molecular clips and tweezers are interesting because of their supramolecular properties, like self-assembling and molecular recognition of small electron-deficient guest molecules (Degen et al., 2007; Klarner et al., 2003). Glycoluril and its derivatives have during the past two decades established an impressive career as a building block during supramolecular chemistry (Freeman et al., 1981; Rowan et al., 1999; Rebek, 2005; Wu, Fettinger et al., 2002). Based on glycouril, molecular clips, molecular tweezers, cucurbituril cotaxanes, molecular mapsules and molecular basket have been designed and synthesized(Rowan et al., 1999; Elemans et al.,2000). As a part of our ongoing investigation of glycoluril derivatives (Li et al., 2006), we report here the structure of the title compound (I) (Fig. 1).
The molecular structure of (I) is shown in Fig. 1. It is a flexible glycouril clip, each N atom from separate rings of which carries an ethyl substituent. Intermolecular non-classical C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).