Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033739/hk2272sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033739/hk2272Isup2.hkl |
CCDC reference: 657763
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.105
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 1983 Count of symmetry unique reflns 1996 Completeness (_total/calc) 99.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Wu et al. (2002); Hof et al. (2002); van Nunen & Nolte (1997); Rowan et al. (1999); Burnett et al. (2003); Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Li et al. (2007); Cao et al. (2006).
The title compound was synthesized according to the reported procedure (Burnett et al., 2003). Crystals appropriate for X-ray data collection were obtained by slow evaporation of the dichloromethane solution at 283 K.
When the crystal structure was solved, the atoms H7A, H7B, C8, H8A, H8B and H8C were found to be disordered. During refinement with isotropic thermal parameters, the occupancies of disordered H atoms were refined as H7A = 0.379 (16), H7C = 0.621 (16), H7B = 0.379 (16), H7D = 0.621 (16), H8A = 0.621 (16), H8D = 0.379 (16), H8B = 0.621 (16), H8E = 0.379 (16), H8C = 0.621 (16) and H8F = 0.379 (16). The remaining site occupancy factors were also refined as C8 = 0.621 (16) and C8' = 0.379 (16) during anisotropic refinement. H atoms were positioned geometrically with C—H = 0.97 and 0.96 Å for methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for methylene H atoms.
The glycoluril skeleton has served as an important building block for the preparation of a wide variety of supramolecular assemblies (Wu et al., 2002; Hof et al., 2002). The title compound is a glycoluril derivative, and is an important intermediate for the preparation of molecular clips (van Nunen et al., 1997). The molecular clip is a molecule with a rigid U-shaped cavity in which small aromatic guest molecules can be complexed by hydrogen bonding and aromatic stacking interactions (Rowan et al., 1999). We report herein the crystal structure of the title glycoluril derivative, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and are in accordance with the corresponding values in similar compounds (Li et al., 2007; Cao et al., 2006). The rings A (O1/N1/N2/C1/C2/C5) and B (O4/N3/N4/C9/C13/C14) are not planar having total puckering amplitudes, QT of 1.844 (3) Å and 2.367 (3) Å, respectively, and chair conformations [φ = -28.16 (2)°, θ = 58.42 (4)° and φ = -90.10 (3)°, θ = 91.04 (3)°] (Cremer & Pople, 1975). Rings C (N1/N3/C3/C5/C9) and D (N2/N4/C4/C5/C9) have pseudo twofold axis passing through atom C9 and the mid-point of C3—N1 bond (for ring C) and atom C5 and the mid-point of C4—N4 bond (for ring D), as can be deduced from the torsion angles (Table 1). The conformations of rings C and D are envelopes, with atoms C3 and C4 at the flap positions, 0.241 (4) Å and 0.231 (3) Å from the mean planes through the other four atoms, respectively.
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.
For related literature, see: Wu et al. (2002); Hof et al. (2002); van Nunen & Nolte (1997); Rowan et al. (1999); Burnett et al. (2003); Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Li et al. (2007); Cao et al. (2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: SHELXTL (Bruker, 2001).
C14H18N4O8 | F(000) = 388 |
Mr = 370.32 | Dx = 1.410 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1973 reflections |
a = 8.3182 (11) Å | θ = 2.4–24.9° |
b = 12.4523 (17) Å | µ = 0.12 mm−1 |
c = 9.0479 (12) Å | T = 292 K |
β = 111.429 (2)° | Block, colourless |
V = 872.4 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 |
Bruker SMART 4 K CCD area-detector diffractometer | 1764 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.0°, θmin = 2.4° |
φ and ω scans | h = −10→9 |
5178 measured reflections | k = −15→15 |
1983 independent reflections | l = −8→11 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0447P] where P = (Fo2 + 2Fc2)/3 |
1983 reflections | (Δ/σ)max = 0.001 |
242 parameters | Δρmax = 0.15 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
C14H18N4O8 | V = 872.4 (2) Å3 |
Mr = 370.32 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.3182 (11) Å | µ = 0.12 mm−1 |
b = 12.4523 (17) Å | T = 292 K |
c = 9.0479 (12) Å | 0.30 × 0.20 × 0.20 mm |
β = 111.429 (2)° |
Bruker SMART 4 K CCD area-detector diffractometer | 1764 reflections with I > 2σ(I) |
5178 measured reflections | Rint = 0.024 |
1983 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 2 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.15 e Å−3 |
1983 reflections | Δρmin = −0.18 e Å−3 |
242 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) | |
O1 | 1.0609 (3) | 0.93348 (19) | 0.0366 (3) | 0.0581 (6) | |
O2 | 0.7355 (3) | 1.1226 (2) | −0.1321 (3) | 0.0696 (7) | |
O3 | 0.7473 (3) | 0.72136 (17) | 0.0037 (3) | 0.0610 (6) | |
O4 | 0.4210 (3) | 0.9097 (2) | −0.1716 (3) | 0.0572 (6) | |
O5 | 1.0440 (4) | 1.0452 (3) | 0.4466 (3) | 0.0810 (8) | |
O6 | 0.8671 (3) | 0.9150 (2) | 0.4617 (3) | 0.0637 (6) | |
O7 | 0.6082 (3) | 1.08850 (19) | 0.3175 (3) | 0.0602 (6) | |
O8 | 0.4464 (3) | 0.9393 (2) | 0.2830 (3) | 0.0627 (7) | |
N1 | 0.8814 (3) | 1.04901 (19) | 0.1154 (3) | 0.0444 (6) | |
N2 | 0.8885 (3) | 0.86029 (18) | 0.1682 (3) | 0.0422 (5) | |
N3 | 0.5932 (3) | 1.0376 (2) | 0.0105 (3) | 0.0430 (5) | |
N4 | 0.6002 (3) | 0.85184 (18) | 0.0845 (3) | 0.0417 (5) | |
C1 | 1.0532 (4) | 0.8542 (3) | 0.1461 (4) | 0.0549 (8) | |
H1A | 1.1469 | 0.8651 | 0.2471 | 0.066* | |
H1B | 1.0666 | 0.7836 | 0.1069 | 0.066* | |
C2 | 1.0460 (4) | 1.0368 (3) | 0.0943 (4) | 0.0561 (8) | |
H2A | 1.0551 | 1.0905 | 0.0201 | 0.067* | |
H2B | 1.1399 | 1.0483 | 0.1951 | 0.067* | |
C3 | 0.7366 (4) | 1.0736 (2) | −0.0172 (4) | 0.0465 (7) | |
C4 | 0.7467 (3) | 0.8029 (2) | 0.0757 (4) | 0.0427 (6) | |
C5 | 0.8418 (3) | 0.9662 (2) | 0.2081 (3) | 0.0384 (6) | |
C6 | 0.9305 (4) | 0.9837 (3) | 0.3875 (4) | 0.0495 (7) | |
C7 | 0.9423 (6) | 0.9107 (4) | 0.6352 (4) | 0.0835 (12) | |
H7A | 1.0499 | 0.9505 | 0.6737 | 0.100* | 0.379 (16) |
H7B | 0.8637 | 0.9424 | 0.6799 | 0.100* | 0.379 (16) |
H7C | 0.9169 | 0.9763 | 0.6799 | 0.100* | 0.621 (16) |
H7D | 1.0655 | 0.9008 | 0.6717 | 0.100* | 0.621 (16) |
C8' | 0.973 (4) | 0.8013 (13) | 0.681 (2) | 0.120 (5) | 0.379 (16) |
H8D | 0.8643 | 0.7644 | 0.6539 | 0.179* | 0.379 (16) |
H8E | 1.0342 | 0.7970 | 0.7939 | 0.179* | 0.379 (16) |
H8F | 1.0400 | 0.7684 | 0.6272 | 0.179* | 0.379 (16) |
C8 | 0.864 (2) | 0.8187 (11) | 0.6818 (12) | 0.120 (5) | 0.621 (16) |
H8B | 0.7419 | 0.8306 | 0.6512 | 0.179* | 0.621 (16) |
H8A | 0.9146 | 0.8095 | 0.7949 | 0.179* | 0.621 (16) |
H8C | 0.8831 | 0.7553 | 0.6302 | 0.179* | 0.621 (16) |
C9 | 0.6399 (3) | 0.9613 (2) | 0.1413 (3) | 0.0371 (6) | |
C10 | 0.5515 (3) | 0.9931 (2) | 0.2571 (3) | 0.0437 (6) | |
C11 | 0.5389 (6) | 1.1295 (4) | 0.4340 (5) | 0.0843 (13) | |
H11A | 0.4160 | 1.1428 | 0.3836 | 0.101* | |
H11B | 0.5569 | 1.0774 | 0.5184 | 0.101* | |
C12 | 0.6285 (8) | 1.2279 (4) | 0.4977 (6) | 0.1070 (18) | |
H12A | 0.7496 | 1.2135 | 0.5494 | 0.161* | |
H12B | 0.5841 | 1.2575 | 0.5730 | 0.161* | |
H12C | 0.6116 | 1.2783 | 0.4130 | 0.161* | |
C13 | 0.4298 (4) | 1.0173 (3) | −0.1184 (4) | 0.0540 (8) | |
H13A | 0.3354 | 1.0311 | −0.0823 | 0.065* | |
H13B | 0.4179 | 1.0657 | −0.2058 | 0.065* | |
C14 | 0.4365 (4) | 0.8373 (3) | −0.0448 (4) | 0.0513 (7) | |
H14A | 0.4276 | 0.7640 | −0.0832 | 0.062* | |
H14B | 0.3430 | 0.8497 | −0.0071 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0501 (11) | 0.0574 (15) | 0.0793 (15) | 0.0006 (10) | 0.0384 (11) | 0.0035 (12) |
O2 | 0.0736 (15) | 0.0679 (17) | 0.0735 (16) | 0.0006 (12) | 0.0340 (13) | 0.0305 (14) |
O3 | 0.0601 (13) | 0.0372 (12) | 0.0925 (16) | 0.0007 (10) | 0.0360 (12) | −0.0151 (12) |
O4 | 0.0512 (11) | 0.0601 (14) | 0.0532 (12) | −0.0013 (11) | 0.0106 (9) | −0.0125 (11) |
O5 | 0.0752 (17) | 0.089 (2) | 0.0687 (16) | −0.0352 (16) | 0.0146 (13) | −0.0135 (15) |
O6 | 0.0672 (13) | 0.0738 (16) | 0.0426 (11) | −0.0190 (12) | 0.0113 (10) | 0.0056 (11) |
O7 | 0.0700 (14) | 0.0540 (13) | 0.0698 (14) | −0.0068 (11) | 0.0413 (11) | −0.0195 (12) |
O8 | 0.0542 (12) | 0.0740 (17) | 0.0763 (15) | −0.0143 (11) | 0.0431 (11) | −0.0126 (13) |
N1 | 0.0419 (12) | 0.0373 (13) | 0.0579 (14) | −0.0052 (10) | 0.0230 (11) | 0.0045 (11) |
N2 | 0.0368 (11) | 0.0353 (12) | 0.0565 (14) | 0.0021 (9) | 0.0195 (10) | 0.0033 (11) |
N3 | 0.0409 (12) | 0.0391 (12) | 0.0492 (13) | 0.0033 (10) | 0.0166 (10) | 0.0024 (11) |
N4 | 0.0365 (11) | 0.0354 (12) | 0.0566 (14) | −0.0031 (9) | 0.0209 (10) | −0.0043 (11) |
C1 | 0.0400 (15) | 0.0481 (18) | 0.080 (2) | 0.0081 (13) | 0.0256 (14) | 0.0042 (17) |
C2 | 0.0431 (16) | 0.0531 (18) | 0.081 (2) | −0.0059 (14) | 0.0326 (15) | 0.0050 (18) |
C3 | 0.0519 (16) | 0.0347 (14) | 0.0573 (17) | 0.0012 (12) | 0.0251 (13) | 0.0034 (13) |
C4 | 0.0446 (15) | 0.0310 (14) | 0.0572 (17) | 0.0017 (11) | 0.0241 (13) | 0.0035 (13) |
C5 | 0.0369 (12) | 0.0335 (13) | 0.0476 (15) | −0.0021 (10) | 0.0188 (11) | −0.0002 (11) |
C6 | 0.0389 (14) | 0.0524 (18) | 0.0527 (17) | −0.0025 (13) | 0.0113 (12) | −0.0023 (14) |
C7 | 0.098 (3) | 0.096 (3) | 0.046 (2) | −0.007 (3) | 0.0133 (19) | 0.004 (2) |
C8' | 0.172 (13) | 0.127 (7) | 0.055 (3) | −0.058 (9) | 0.037 (7) | 0.011 (4) |
C8 | 0.172 (13) | 0.127 (7) | 0.055 (3) | −0.058 (9) | 0.037 (7) | 0.011 (4) |
C9 | 0.0358 (12) | 0.0320 (13) | 0.0447 (15) | −0.0019 (10) | 0.0159 (11) | −0.0020 (11) |
C10 | 0.0383 (13) | 0.0459 (16) | 0.0485 (15) | −0.0005 (11) | 0.0177 (11) | −0.0038 (13) |
C11 | 0.095 (3) | 0.084 (3) | 0.091 (3) | −0.003 (2) | 0.055 (3) | −0.036 (2) |
C12 | 0.172 (5) | 0.074 (3) | 0.084 (3) | 0.002 (3) | 0.057 (3) | −0.025 (3) |
C13 | 0.0450 (16) | 0.0562 (19) | 0.0551 (17) | 0.0096 (13) | 0.0113 (13) | 0.0024 (15) |
C14 | 0.0438 (15) | 0.0459 (17) | 0.064 (2) | −0.0068 (13) | 0.0195 (13) | −0.0103 (14) |
C1—O1 | 1.416 (4) | C8'—H8D | 0.9600 |
C1—N2 | 1.458 (4) | C8'—H8E | 0.9600 |
C1—H1A | 0.9700 | C8'—H8F | 0.9600 |
C1—H1B | 0.9700 | C8—H8B | 0.9600 |
C2—O1 | 1.411 (4) | C8—H8A | 0.9600 |
C2—N1 | 1.458 (4) | C8—H8C | 0.9600 |
C2—H2A | 0.9700 | C9—N4 | 1.451 (4) |
C2—H2B | 0.9700 | C9—N3 | 1.455 (4) |
C3—O2 | 1.203 (4) | C9—C10 | 1.536 (4) |
C3—N3 | 1.380 (4) | C10—O8 | 1.191 (3) |
C3—N1 | 1.389 (4) | C10—O7 | 1.320 (4) |
C4—O3 | 1.208 (4) | C11—C12 | 1.441 (7) |
C4—N2 | 1.371 (4) | C11—O7 | 1.466 (4) |
C4—N4 | 1.390 (3) | C11—H11A | 0.9700 |
C5—N1 | 1.442 (4) | C11—H11B | 0.9700 |
C5—N2 | 1.457 (3) | C12—H12A | 0.9600 |
C5—C6 | 1.533 (4) | C12—H12B | 0.9600 |
C5—C9 | 1.565 (3) | C12—H12C | 0.9600 |
C6—O5 | 1.181 (4) | C13—O4 | 1.417 (4) |
C6—O6 | 1.311 (4) | C13—N3 | 1.454 (4) |
C7—C8' | 1.420 (16) | C13—H13A | 0.9700 |
C7—C8 | 1.455 (10) | C13—H13B | 0.9700 |
C7—O6 | 1.463 (4) | C14—O4 | 1.427 (4) |
C7—H7A | 0.9700 | C14—N4 | 1.447 (4) |
C7—H7B | 0.9700 | C14—H14A | 0.9700 |
C7—H7C | 0.9692 | C14—H14B | 0.9700 |
C7—H7D | 0.9628 | ||
C2—O1—C1 | 110.1 (2) | C8—C7—H7C | 110.7 |
C13—O4—C14 | 110.3 (2) | O6—C7—H7C | 110.1 |
C6—O6—C7 | 118.6 (3) | H7A—C7—H7C | 74.4 |
C10—O7—C11 | 115.8 (3) | C8'—C7—H7D | 74.0 |
C3—N1—C5 | 110.5 (2) | C8—C7—H7D | 109.5 |
C3—N1—C2 | 118.0 (3) | O6—C7—H7D | 110.9 |
C5—N1—C2 | 115.3 (2) | H7B—C7—H7D | 134.8 |
C4—N2—C5 | 112.0 (2) | H7C—C7—H7D | 109.4 |
C4—N2—C1 | 122.1 (3) | C7—C8'—H8D | 109.5 |
C5—N2—C1 | 115.5 (2) | H7D—C8'—H8D | 147.9 |
C3—N3—C13 | 121.8 (3) | C7—C8'—H8E | 109.5 |
C3—N3—C9 | 111.6 (2) | H7D—C8'—H8E | 91.2 |
C13—N3—C9 | 115.6 (2) | C7—C8'—H8F | 109.4 |
C4—N4—C14 | 119.0 (2) | H7D—C8'—H8F | 84.9 |
C4—N4—C9 | 109.9 (2) | C7—C8—H8B | 109.5 |
C14—N4—C9 | 115.4 (2) | C7—C8—H8A | 109.5 |
O1—C1—N2 | 110.2 (2) | H8B—C8—H8A | 109.5 |
O1—C1—H1A | 109.6 | C7—C8—H8C | 109.4 |
N2—C1—H1A | 109.6 | H8B—C8—H8C | 109.5 |
O1—C1—H1B | 109.6 | H8A—C8—H8C | 109.5 |
N2—C1—H1B | 109.6 | N4—C9—N3 | 111.5 (2) |
H1A—C1—H1B | 108.1 | N4—C9—C10 | 112.4 (2) |
O1—C2—N1 | 110.9 (2) | N3—C9—C10 | 109.5 (2) |
O1—C2—H2A | 109.5 | N4—C9—C5 | 104.3 (2) |
N1—C2—H2A | 109.5 | N3—C9—C5 | 102.6 (2) |
O1—C2—H2B | 109.5 | C10—C9—C5 | 116.1 (2) |
N1—C2—H2B | 109.5 | O8—C10—O7 | 127.0 (3) |
H2A—C2—H2B | 108.0 | O8—C10—C9 | 123.9 (3) |
O2—C3—N3 | 126.0 (3) | O7—C10—C9 | 109.1 (2) |
O2—C3—N1 | 126.1 (3) | C12—C11—O7 | 107.5 (4) |
N3—C3—N1 | 107.8 (3) | C12—C11—H11A | 110.2 |
O3—C4—N2 | 126.5 (3) | O7—C11—H11A | 110.2 |
O3—C4—N4 | 125.2 (3) | C12—C11—H11B | 110.2 |
N2—C4—N4 | 108.3 (2) | O7—C11—H11B | 110.2 |
N1—C5—N2 | 111.4 (2) | H11A—C11—H11B | 108.5 |
N1—C5—C6 | 113.0 (2) | C11—C12—H12A | 109.5 |
N2—C5—C6 | 108.8 (2) | C11—C12—H12B | 109.5 |
N1—C5—C9 | 104.1 (2) | H12A—C12—H12B | 109.5 |
N2—C5—C9 | 102.4 (2) | C11—C12—H12C | 109.5 |
C6—C5—C9 | 116.6 (2) | H12A—C12—H12C | 109.5 |
O5—C6—O6 | 126.5 (3) | H12B—C12—H12C | 109.5 |
O5—C6—C5 | 124.6 (3) | O4—C13—N3 | 110.7 (2) |
O6—C6—C5 | 108.8 (2) | O4—C13—H13A | 109.5 |
C8'—C7—O6 | 108.1 (9) | N3—C13—H13A | 109.5 |
C8—C7—O6 | 106.2 (5) | O4—C13—H13B | 109.5 |
C8'—C7—H7A | 110.1 | N3—C13—H13B | 109.5 |
C8—C7—H7A | 138.7 | H13A—C13—H13B | 108.1 |
O6—C7—H7A | 110.1 | O4—C14—N4 | 110.7 (2) |
C8'—C7—H7B | 110.0 | O4—C14—H14A | 109.5 |
C8—C7—H7B | 75.9 | N4—C14—H14A | 109.5 |
O6—C7—H7B | 110.1 | O4—C14—H14B | 109.5 |
H7A—C7—H7B | 108.4 | N4—C14—H14B | 109.5 |
C8'—C7—H7C | 136.8 | H14A—C14—H14B | 108.1 |
N2—C1—O1—C2 | 60.7 (3) | N1—C5—C9—N4 | 120.5 (2) |
O1—C1—N2—C4 | 90.1 (3) | N2—C5—C9—N4 | 4.3 (3) |
O1—C1—N2—C5 | −52.1 (4) | C6—C5—C9—N4 | −114.3 (3) |
N1—C2—O1—C1 | −60.9 (3) | N1—C5—C9—N3 | 4.1 (3) |
O1—C2—N1—C3 | −81.6 (3) | N2—C5—C9—N3 | −112.1 (2) |
O1—C2—N1—C5 | 52.0 (4) | C6—C5—C9—N3 | 129.3 (2) |
O2—C3—N1—C5 | −164.3 (3) | N1—C5—C9—C10 | −115.4 (3) |
N3—C3—N1—C5 | 19.3 (3) | N2—C5—C9—C10 | 128.5 (2) |
O2—C3—N1—C2 | −28.6 (5) | C6—C5—C9—C10 | 9.9 (3) |
N3—C3—N1—C2 | 155.0 (3) | O5—C6—O6—C7 | −0.7 (6) |
O2—C3—N3—C13 | 24.5 (5) | C5—C6—O6—C7 | 175.2 (3) |
N1—C3—N3—C13 | −159.0 (3) | C8'—C7—O6—C6 | −132.7 (13) |
O2—C3—N3—C9 | 167.1 (3) | C8—C7—O6—C6 | −172.3 (9) |
N1—C3—N3—C9 | −16.5 (3) | N4—C9—N3—C3 | −103.8 (3) |
O3—C4—N2—C5 | 167.0 (3) | C10—C9—N3—C3 | 131.2 (2) |
N4—C4—N2—C5 | −15.9 (3) | C5—C9—N3—C3 | 7.3 (3) |
O3—C4—N2—C1 | 23.7 (5) | N4—C9—N3—C13 | 41.3 (3) |
N4—C4—N2—C1 | −159.2 (3) | C10—C9—N3—C13 | −83.8 (3) |
O3—C4—N4—C14 | −27.8 (4) | C5—C9—N3—C13 | 152.4 (2) |
N2—C4—N4—C14 | 155.0 (2) | N3—C9—N4—C4 | 96.1 (2) |
O3—C4—N4—C9 | −164.1 (3) | C10—C9—N4—C4 | −140.5 (2) |
N2—C4—N4—C9 | 18.7 (3) | C5—C9—N4—C4 | −13.9 (3) |
N2—C5—N1—C3 | 95.5 (3) | N3—C9—N4—C14 | −41.8 (3) |
C6—C5—N1—C3 | −141.7 (2) | C10—C9—N4—C14 | 81.6 (3) |
C9—C5—N1—C3 | −14.2 (3) | C5—C9—N4—C14 | −151.9 (2) |
N2—C5—N1—C2 | −41.5 (3) | N4—C9—C10—O8 | −8.5 (4) |
C6—C5—N1—C2 | 81.3 (3) | N3—C9—C10—O8 | 116.1 (3) |
C9—C5—N1—C2 | −151.1 (2) | C5—C9—C10—O8 | −128.3 (3) |
N1—C5—N2—C4 | −104.0 (3) | N4—C9—C10—O7 | 173.0 (2) |
C6—C5—N2—C4 | 130.8 (2) | N3—C9—C10—O7 | −62.5 (3) |
C9—C5—N2—C4 | 6.7 (3) | C5—C9—C10—O7 | 53.1 (3) |
N1—C5—N2—C1 | 41.9 (3) | O8—C10—O7—C11 | 2.9 (5) |
C6—C5—N2—C1 | −83.3 (3) | C9—C10—O7—C11 | −178.6 (3) |
C9—C5—N2—C1 | 152.6 (2) | C12—C11—O7—C10 | 174.1 (4) |
N1—C5—C6—O5 | −13.6 (4) | N3—C13—O4—C14 | 59.8 (3) |
N2—C5—C6—O5 | 110.6 (4) | O4—C13—N3—C3 | 90.0 (4) |
C9—C5—C6—O5 | −134.3 (4) | O4—C13—N3—C9 | −51.1 (3) |
N1—C5—C6—O6 | 170.4 (2) | O4—C14—N4—C4 | −81.8 (3) |
N2—C5—C6—O6 | −65.4 (3) | O4—C14—N4—C9 | 52.2 (3) |
C9—C5—C6—O6 | 49.7 (3) | N4—C14—O4—C13 | −60.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O8i | 0.97 | 2.56 | 3.223 (4) | 125 |
C1—H1B···O2ii | 0.97 | 2.55 | 3.404 (4) | 147 |
C2—H2A···O3iii | 0.97 | 2.38 | 3.183 (4) | 140 |
C8—H8A···O1iv | 0.96 | 2.59 | 3.345 (12) | 136 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z; (iii) −x+2, y+1/2, −z; (iv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H18N4O8 |
Mr | 370.32 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 292 |
a, b, c (Å) | 8.3182 (11), 12.4523 (17), 9.0479 (12) |
β (°) | 111.429 (2) |
V (Å3) | 872.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 4 K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5178, 1983, 1764 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.105, 1.11 |
No. of reflections | 1983 |
No. of parameters | 242 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
N3—C3—N1—C5 | 19.3 (3) | C9—C5—N2—C4 | 6.7 (3) |
N1—C3—N3—C9 | −16.5 (3) | N2—C5—C9—N4 | 4.3 (3) |
N4—C4—N2—C5 | −15.9 (3) | N1—C5—C9—N3 | 4.1 (3) |
N2—C4—N4—C9 | 18.7 (3) | C5—C9—N3—C3 | 7.3 (3) |
C9—C5—N1—C3 | −14.2 (3) | C5—C9—N4—C4 | −13.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O8i | 0.97 | 2.56 | 3.223 (4) | 125.4 |
C1—H1B···O2ii | 0.97 | 2.55 | 3.404 (4) | 146.8 |
C2—H2A···O3iii | 0.97 | 2.38 | 3.183 (4) | 140.0 |
C8—H8A···O1iv | 0.96 | 2.59 | 3.345 (12) | 135.8 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z; (iii) −x+2, y+1/2, −z; (iv) x, y, z+1. |
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The glycoluril skeleton has served as an important building block for the preparation of a wide variety of supramolecular assemblies (Wu et al., 2002; Hof et al., 2002). The title compound is a glycoluril derivative, and is an important intermediate for the preparation of molecular clips (van Nunen et al., 1997). The molecular clip is a molecule with a rigid U-shaped cavity in which small aromatic guest molecules can be complexed by hydrogen bonding and aromatic stacking interactions (Rowan et al., 1999). We report herein the crystal structure of the title glycoluril derivative, (I).
In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and are in accordance with the corresponding values in similar compounds (Li et al., 2007; Cao et al., 2006). The rings A (O1/N1/N2/C1/C2/C5) and B (O4/N3/N4/C9/C13/C14) are not planar having total puckering amplitudes, QT of 1.844 (3) Å and 2.367 (3) Å, respectively, and chair conformations [φ = -28.16 (2)°, θ = 58.42 (4)° and φ = -90.10 (3)°, θ = 91.04 (3)°] (Cremer & Pople, 1975). Rings C (N1/N3/C3/C5/C9) and D (N2/N4/C4/C5/C9) have pseudo twofold axis passing through atom C9 and the mid-point of C3—N1 bond (for ring C) and atom C5 and the mid-point of C4—N4 bond (for ring D), as can be deduced from the torsion angles (Table 1). The conformations of rings C and D are envelopes, with atoms C3 and C4 at the flap positions, 0.241 (4) Å and 0.231 (3) Å from the mean planes through the other four atoms, respectively.
In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.