Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032485/rk2021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032485/rk2021Isup2.hkl |
CCDC reference: 657702
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.152
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.78 Ratio
Author Response: It may be due to some disorder in the ethyl group. |
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.29 Ratio
Author Response: This could results from some disorder of the nearby ethyl group. |
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc. PLAT318_ALERT_2_C Check Hybridisation of N2 in Main Residue . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 13.60 Deg. C7 -C6 -C7' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 2.60 Deg. H6A -C6 -H6C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 6.40 Deg. H6B -C6 -H6D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.20 Deg. C11 -C10 -C11' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.10 Deg. H10B -C10 -H10C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 37.60 Deg. H10A -C10 -H10D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.70 Deg. C10 -C11 -H10C 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 45
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 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 12 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: Burnett et al. (2003); Chen et al. (2007); Himes et al. (1978); Hof et al. (2002); Isaacs & Witt (2002); Kim et al. (2000); Li et al. (1994); Moon et al. (2003); Rowan et al. (1999); Wang et al. (2006); Wu et al. (2002).
The title compound was synthesized according to literature procedure (Burnett et al., 2003) in 52% isolated yield. Crystals appropriate for data collection were obtained by slow evaporation of CH3OH solution at room temperature.
Two ethyl group were found to be disordered over two orientations. The occupancies of the disordered positions C7/ C7' and C8/ C8' refined to 0.60 (4) / 0.40 (4), C11 / C11' and C12 / C12', refined to 0.609 (7) / 0.391 (7). In addition, there is also some disorder in the H atoms of C6 and C10 oweing to disorder of its nearby ethyl group. All other H-atoms bound to carbon were positioned geometrically idealized positions and constrained to ride on their parent atoms, with d(C–H) = 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms, and with d(N–H) = 0.86 Å, Uiso (H) = 1.2Ueq (N).
Glycoluril –C4H6N4O2– skeleton moiety of the title compound (scheme 1) is an important building block for both molecular and supramolecular chemistry. Its derivatives have been used as the basis for molecular capsules (Hof et al., 2002), molecular clips (Rowan et al., 1999), self-complementary facial amphiphiles (Isaacs & Witt, 2002), and the cucurbit[n]uril (CB[n]) family (Kim et al., 2000), and its utilization has been explored as a platform for studies of crystal engineering (Wang et al., 2006; Chen et al., 2007). Despite a variety of crystal structures reported for a number of its derivatives, relatively few crystal structures are known for glycoluril derivatives without N-substituents, which exhibit two different H-bonded types (scheme 2). The mode A have been found for (R = H) (Li et al., 1994), (R = CH3) (Himes et al., 1978), (R = Ph) (Wu et al., 2002), and so on, but the mode B, so far was only observed in the (R = Ph) (Moon et al., 2003). Herein, we report the crystal structure of the title compound with R = –COO–n-C3H7) (Fig. 1), which exhibits the scarce mode B of hydrogen bonding (scheme 2).
In the crystal structure, the two-dimension hydrogen bonding network, shown in Fig. 2, is based on the formation of eight-membered rings and ten-membered rings H-bonding motifs. This is fully according with the scarce mode B of hydrogen bonding (scheme 2). While the mode A, reported in the crystal structure of the (scheme 2, R = H, CH3, Ph), is only made up of eight-membered rings H-bonding motifs. In addition, intermolecular C10–H10B···O3 interactions (see table) can stabilize the crystal structure.
For related literature, see: Burnett et al. (2003); Chen et al. (2007); Himes et al. (1978); Hof et al. (2002); Isaacs & Witt (2002); Kim et al. (2000); Li et al. (1994); Moon et al. (2003); Rowan et al. (1999); Wang et al. (2006); Wu et al. (2002).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); 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, 1997).
C12H18N4O6 | F(000) = 1328 |
Mr = 314.30 | Dx = 1.356 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5455 reflections |
a = 13.3013 (7) Å | θ = 2.5–27.1° |
b = 11.5852 (6) Å | µ = 0.11 mm−1 |
c = 19.9867 (10) Å | T = 300 K |
V = 3079.9 (3) Å3 | Plate, colorless |
Z = 8 | 0.20 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 2887 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 28.3°, θmin = 2.0° |
φ and ω scans | h = −11→17 |
20966 measured reflections | k = −15→15 |
3752 independent reflections | l = −26→26 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | |
3752 reflections | (Δ/σ)max = 0.001 |
241 parameters | Δρmax = 0.41 e Å−3 |
45 restraints | Δρmin = −0.25 e Å−3 |
C12H18N4O6 | V = 3079.9 (3) Å3 |
Mr = 314.30 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 13.3013 (7) Å | µ = 0.11 mm−1 |
b = 11.5852 (6) Å | T = 300 K |
c = 19.9867 (10) Å | 0.20 × 0.20 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 2887 reflections with I > 2σ(I) |
20966 measured reflections | Rint = 0.060 |
3752 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 45 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.41 e Å−3 |
3752 reflections | Δρmin = −0.25 e Å−3 |
241 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 > 2σ(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 | 0.75770 (11) | −0.07104 (12) | 0.27047 (7) | 0.0268 (3) | |
C2 | 0.99691 (11) | 0.11085 (12) | 0.25548 (8) | 0.0287 (3) | |
C3 | 0.91169 (11) | −0.02387 (12) | 0.31998 (8) | 0.0251 (3) | |
C4 | 0.84418 (10) | 0.08686 (12) | 0.31140 (8) | 0.0260 (3) | |
C5 | 0.93005 (12) | −0.06780 (13) | 0.39124 (8) | 0.0332 (4) | |
C6 | 0.85324 (15) | −0.09772 (19) | 0.49676 (9) | 0.0519 (5) | |
H6A | 0.9205 | −0.0884 | 0.5148 | 0.062* | 0.60 (4) |
H6B | 0.8390 | −0.1798 | 0.4947 | 0.062* | 0.60 (4) |
H6C | 0.9199 | −0.0914 | 0.5161 | 0.062* | 0.40 (4) |
H6D | 0.8322 | −0.1779 | 0.4975 | 0.062* | 0.40 (4) |
C7 | 0.7798 (6) | −0.0418 (10) | 0.5431 (5) | 0.051 (2) | 0.60 (4) |
H7A | 0.7146 | −0.0361 | 0.5216 | 0.061* | 0.60 (4) |
H7B | 0.8023 | 0.0356 | 0.5540 | 0.061* | 0.60 (4) |
C8 | 0.7710 (8) | −0.1140 (18) | 0.6072 (3) | 0.086 (3) | 0.60 (4) |
H8A | 0.7477 | −0.1901 | 0.5962 | 0.130* | 0.60 (4) |
H8B | 0.7242 | −0.0780 | 0.6372 | 0.130* | 0.60 (4) |
H8C | 0.8357 | −0.1191 | 0.6284 | 0.130* | 0.60 (4) |
C7' | 0.7807 (13) | −0.0185 (17) | 0.5315 (9) | 0.084 (4) | 0.40 (4) |
H7'1 | 0.7175 | −0.0168 | 0.5074 | 0.101* | 0.40 (4) |
H7'2 | 0.8078 | 0.0592 | 0.5327 | 0.101* | 0.40 (4) |
C8' | 0.7635 (12) | −0.063 (2) | 0.6031 (7) | 0.085 (4) | 0.40 (4) |
H8'1 | 0.7223 | −0.1306 | 0.6019 | 0.127* | 0.40 (4) |
H8'2 | 0.7304 | −0.0039 | 0.6289 | 0.127* | 0.40 (4) |
H8'3 | 0.8270 | −0.0808 | 0.6233 | 0.127* | 0.40 (4) |
C9 | 0.82776 (12) | 0.16353 (13) | 0.37327 (9) | 0.0332 (4) | |
C10 | 0.91527 (18) | 0.27569 (18) | 0.45434 (11) | 0.0592 (6) | |
H10A | 0.8515 | 0.3163 | 0.4550 | 0.071* | 0.609 (7) |
H10B | 0.9227 | 0.2355 | 0.4966 | 0.071* | 0.609 (7) |
H10C | 0.9666 | 0.2577 | 0.4872 | 0.071* | 0.391 (7) |
H10D | 0.8503 | 0.2768 | 0.4763 | 0.071* | 0.391 (7) |
C11 | 0.9967 (4) | 0.3581 (3) | 0.4464 (2) | 0.0615 (14) | 0.609 (7) |
H11A | 1.0587 | 0.3163 | 0.4385 | 0.074* | 0.609 (7) |
H11B | 1.0044 | 0.4012 | 0.4877 | 0.074* | 0.609 (7) |
C12 | 0.9801 (6) | 0.4412 (5) | 0.3901 (3) | 0.104 (3) | 0.609 (7) |
H12A | 0.9778 | 0.3997 | 0.3485 | 0.157* | 0.609 (7) |
H12B | 1.0342 | 0.4960 | 0.3889 | 0.157* | 0.609 (7) |
H12C | 0.9176 | 0.4811 | 0.3967 | 0.157* | 0.609 (7) |
C11' | 0.9364 (6) | 0.3945 (7) | 0.4212 (4) | 0.078 (3) | 0.391 (7) |
H11C | 0.8867 | 0.4092 | 0.3868 | 0.093* | 0.391 (7) |
H11D | 0.9311 | 0.4550 | 0.4546 | 0.093* | 0.391 (7) |
C12' | 1.0388 (8) | 0.3958 (10) | 0.3912 (6) | 0.120 (5) | 0.391 (7) |
H12D | 1.0881 | 0.3863 | 0.4258 | 0.180* | 0.391 (7) |
H12E | 1.0496 | 0.4681 | 0.3688 | 0.180* | 0.391 (7) |
H12F | 1.0447 | 0.3339 | 0.3595 | 0.180* | 0.391 (7) |
N1 | 0.75121 (9) | 0.04142 (11) | 0.28776 (7) | 0.0301 (3) | |
H1 | 0.6968 | 0.0813 | 0.2848 | 0.036* | |
N2 | 0.85239 (9) | −0.10854 (10) | 0.28403 (7) | 0.0286 (3) | |
H2 | 0.8747 | −0.1753 | 0.2725 | 0.034* | |
N3 | 1.00441 (9) | 0.00930 (11) | 0.28903 (7) | 0.0313 (3) | |
H3 | 1.0588 | −0.0307 | 0.2914 | 0.038* | |
N4 | 0.90195 (10) | 0.15112 (10) | 0.26255 (7) | 0.0298 (3) | |
H4 | 0.8784 | 0.2087 | 0.2404 | 0.036* | |
O1 | 0.68919 (9) | −0.12847 (9) | 0.24606 (6) | 0.0383 (3) | |
O2 | 1.06484 (9) | 0.15783 (9) | 0.22415 (7) | 0.0411 (3) | |
O3 | 1.00591 (10) | −0.11525 (15) | 0.40724 (7) | 0.0622 (4) | |
O4 | 0.85052 (9) | −0.05045 (11) | 0.42944 (6) | 0.0417 (3) | |
O5 | 0.74722 (10) | 0.19561 (12) | 0.39100 (7) | 0.0535 (4) | |
O6 | 0.91566 (9) | 0.19233 (11) | 0.39968 (7) | 0.0468 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0263 (8) | 0.0219 (7) | 0.0322 (8) | −0.0029 (6) | 0.0012 (6) | 0.0022 (6) |
C2 | 0.0241 (8) | 0.0195 (7) | 0.0426 (9) | −0.0010 (6) | 0.0011 (7) | −0.0021 (6) |
C3 | 0.0197 (7) | 0.0196 (6) | 0.0361 (8) | 0.0011 (5) | −0.0002 (6) | −0.0005 (5) |
C4 | 0.0198 (7) | 0.0201 (6) | 0.0380 (8) | 0.0008 (5) | −0.0004 (6) | −0.0031 (6) |
C5 | 0.0284 (8) | 0.0320 (8) | 0.0391 (9) | −0.0012 (7) | −0.0036 (7) | 0.0003 (6) |
C6 | 0.0544 (12) | 0.0682 (13) | 0.0332 (10) | −0.0090 (10) | −0.0026 (9) | 0.0028 (9) |
C7 | 0.048 (3) | 0.075 (4) | 0.030 (3) | −0.008 (2) | 0.006 (2) | −0.011 (2) |
C8 | 0.103 (5) | 0.123 (7) | 0.034 (2) | −0.011 (5) | 0.009 (2) | 0.011 (3) |
C7' | 0.094 (7) | 0.116 (8) | 0.043 (5) | −0.031 (6) | 0.007 (5) | 0.004 (5) |
C8' | 0.087 (6) | 0.110 (9) | 0.057 (5) | −0.019 (6) | 0.000 (4) | 0.000 (5) |
C9 | 0.0315 (9) | 0.0251 (7) | 0.0430 (9) | 0.0028 (6) | 0.0002 (7) | −0.0062 (6) |
C10 | 0.0708 (15) | 0.0514 (12) | 0.0553 (12) | −0.0015 (10) | −0.0096 (11) | −0.0270 (10) |
C11 | 0.079 (3) | 0.0429 (19) | 0.063 (2) | −0.0114 (19) | −0.031 (2) | −0.0083 (16) |
C12 | 0.144 (7) | 0.084 (4) | 0.085 (4) | −0.031 (4) | −0.028 (4) | 0.036 (3) |
C11' | 0.088 (5) | 0.067 (4) | 0.077 (5) | 0.007 (4) | −0.025 (4) | −0.025 (4) |
C12' | 0.139 (8) | 0.102 (7) | 0.118 (8) | −0.038 (6) | −0.003 (7) | −0.012 (6) |
N1 | 0.0187 (6) | 0.0230 (6) | 0.0487 (8) | 0.0023 (5) | −0.0036 (6) | −0.0057 (5) |
N2 | 0.0277 (7) | 0.0174 (6) | 0.0408 (7) | 0.0018 (5) | −0.0026 (5) | −0.0035 (5) |
N3 | 0.0199 (6) | 0.0240 (6) | 0.0501 (8) | 0.0047 (5) | 0.0040 (6) | 0.0052 (5) |
N4 | 0.0253 (7) | 0.0194 (6) | 0.0448 (8) | 0.0035 (5) | 0.0018 (6) | 0.0048 (5) |
O1 | 0.0330 (7) | 0.0269 (6) | 0.0550 (7) | −0.0087 (5) | −0.0095 (5) | −0.0014 (5) |
O2 | 0.0289 (6) | 0.0265 (6) | 0.0680 (9) | −0.0009 (5) | 0.0115 (6) | 0.0067 (5) |
O3 | 0.0410 (8) | 0.0915 (12) | 0.0542 (8) | 0.0207 (8) | −0.0054 (7) | 0.0231 (8) |
O4 | 0.0395 (7) | 0.0493 (7) | 0.0363 (7) | 0.0050 (6) | 0.0028 (5) | 0.0045 (5) |
O5 | 0.0361 (7) | 0.0624 (9) | 0.0619 (9) | 0.0122 (6) | 0.0054 (6) | −0.0249 (7) |
O6 | 0.0367 (7) | 0.0439 (7) | 0.0597 (8) | 0.0001 (6) | −0.0070 (6) | −0.0257 (6) |
C1—O1 | 1.2291 (18) | C7'—H7'2 | 0.9700 |
C1—N1 | 1.3507 (19) | C8'—H8'1 | 0.9600 |
C1—N2 | 1.3596 (19) | C8'—H8'2 | 0.9600 |
C2—O2 | 1.2268 (18) | C8'—H8'3 | 0.9600 |
C2—N4 | 1.3538 (19) | C9—O5 | 1.1880 (19) |
C2—N3 | 1.3577 (19) | C9—O6 | 1.326 (2) |
C3—N3 | 1.4323 (19) | C10—C11 | 1.452 (4) |
C3—N2 | 1.4494 (18) | C10—O6 | 1.458 (2) |
C3—C5 | 1.532 (2) | C10—C11' | 1.552 (9) |
C3—C4 | 1.5752 (19) | C10—H10A | 0.9700 |
C4—N1 | 1.4247 (18) | C10—H10B | 0.9700 |
C4—N4 | 1.4485 (19) | C10—H10C | 0.9700 |
C4—C9 | 1.538 (2) | C10—H10D | 0.9700 |
C5—O3 | 1.193 (2) | C11—C12 | 1.498 (5) |
C5—O4 | 1.320 (2) | C11—H11A | 0.9700 |
C6—O4 | 1.453 (2) | C11—H11B | 0.9700 |
C6—C7 | 1.494 (4) | C12—H12A | 0.9600 |
C6—C7' | 1.501 (8) | C12—H12B | 0.9600 |
C6—H6A | 0.9700 | C12—H12C | 0.9600 |
C6—H6B | 0.9700 | C11'—C12' | 1.489 (8) |
C6—H6C | 0.9700 | C11'—H11C | 0.9700 |
C6—H6D | 0.9700 | C11'—H11D | 0.9700 |
C7—C8 | 1.535 (7) | C12'—H12D | 0.9600 |
C7—H7A | 0.9700 | C12'—H12E | 0.9600 |
C7—H7B | 0.9700 | C12'—H12F | 0.9600 |
C8—H8A | 0.9600 | N1—H1 | 0.8600 |
C8—H8B | 0.9600 | N2—H2 | 0.8600 |
C8—H8C | 0.9600 | N3—H3 | 0.8600 |
C7'—C8' | 1.538 (9) | N4—H4 | 0.8600 |
C7'—H7'1 | 0.9700 | ||
O1—C1—N1 | 125.19 (14) | O5—C9—O6 | 126.72 (15) |
O1—C1—N2 | 126.36 (14) | O5—C9—C4 | 123.27 (15) |
N1—C1—N2 | 108.44 (12) | O6—C9—C4 | 109.88 (13) |
O2—C2—N4 | 125.99 (14) | C11—C10—O6 | 110.5 (2) |
O2—C2—N3 | 125.61 (14) | C11—C10—C11' | 40.2 (3) |
N4—C2—N3 | 108.40 (13) | O6—C10—C11' | 105.5 (3) |
N3—C3—N2 | 115.85 (12) | C11—C10—H10A | 109.5 |
N3—C3—C5 | 110.70 (12) | O6—C10—H10A | 109.5 |
N2—C3—C5 | 108.84 (12) | C11'—C10—H10A | 74.6 |
N3—C3—C4 | 103.02 (11) | C11—C10—H10B | 109.5 |
N2—C3—C4 | 100.78 (11) | O6—C10—H10B | 109.5 |
C5—C3—C4 | 117.55 (12) | C11'—C10—H10B | 141.1 |
N1—C4—N4 | 115.26 (13) | H10A—C10—H10B | 108.1 |
N1—C4—C9 | 110.90 (12) | C11—C10—H10C | 72.0 |
N4—C4—C9 | 108.70 (11) | O6—C10—H10C | 111.2 |
N1—C4—C3 | 103.30 (11) | C11'—C10—H10C | 110.6 |
N4—C4—C3 | 100.92 (11) | H10A—C10—H10C | 135.3 |
C9—C4—C3 | 117.63 (13) | H10B—C10—H10C | 40.1 |
O3—C5—O4 | 126.36 (16) | C11—C10—H10D | 134.9 |
O3—C5—C3 | 122.50 (15) | O6—C10—H10D | 110.6 |
O4—C5—C3 | 111.07 (13) | C11'—C10—H10D | 110.0 |
O4—C6—C7 | 113.2 (5) | H10A—C10—H10D | 37.6 |
O4—C6—C7' | 100.5 (8) | H10B—C10—H10D | 72.7 |
C7—C6—C7' | 13.6 (7) | H10C—C10—H10D | 108.9 |
O4—C6—H6A | 108.9 | C10—C11—C12 | 113.3 (4) |
C7—C6—H6A | 108.9 | C10—C11—H10C | 38.7 |
C7'—C6—H6A | 110.6 | C12—C11—H10C | 151.9 |
O4—C6—H6B | 108.9 | C10—C11—H11A | 108.9 |
C7—C6—H6B | 108.9 | C12—C11—H11A | 108.9 |
C7'—C6—H6B | 119.6 | H10C—C11—H11A | 85.8 |
H6A—C6—H6B | 107.7 | C10—C11—H11B | 108.9 |
O4—C6—H6C | 111.3 | C12—C11—H11B | 108.9 |
C7—C6—H6C | 108.5 | H10C—C11—H11B | 88.0 |
C7'—C6—H6C | 110.9 | H11A—C11—H11B | 107.7 |
H6A—C6—H6C | 2.6 | C12'—C11'—C10 | 110.3 (7) |
H6B—C6—H6C | 105.6 | C12'—C11'—H11C | 109.6 |
O4—C6—H6D | 111.6 | C10—C11'—H11C | 109.6 |
C7—C6—H6D | 102.6 | C12'—C11'—H11D | 109.6 |
C7'—C6—H6D | 113.2 | C10—C11'—H11D | 109.6 |
H6A—C6—H6D | 111.5 | H11C—C11'—H11D | 108.1 |
H6B—C6—H6D | 6.4 | C11'—C12'—H12D | 109.5 |
H6C—C6—H6D | 109.2 | C11'—C12'—H12E | 109.5 |
C6—C7—C8 | 109.3 (5) | H12D—C12'—H12E | 109.5 |
C6—C7—H7A | 109.8 | C11'—C12'—H12F | 109.5 |
C8—C7—H7A | 109.8 | H12D—C12'—H12F | 109.5 |
C6—C7—H7B | 109.8 | H12E—C12'—H12F | 109.5 |
C8—C7—H7B | 109.8 | C1—N1—C4 | 112.70 (12) |
H7A—C7—H7B | 108.3 | C1—N1—H1 | 123.7 |
C6—C7'—C8' | 108.9 (8) | C4—N1—H1 | 123.7 |
C6—C7'—H7'1 | 109.9 | C1—N2—C3 | 112.75 (12) |
C8'—C7'—H7'1 | 109.9 | C1—N2—H2 | 123.6 |
C6—C7'—H7'2 | 109.9 | C3—N2—H2 | 123.6 |
C8'—C7'—H7'2 | 109.9 | C2—N3—C3 | 112.49 (12) |
H7'1—C7'—H7'2 | 108.3 | C2—N3—H3 | 123.8 |
C7'—C8'—H8'1 | 109.5 | C3—N3—H3 | 123.8 |
C7'—C8'—H8'2 | 109.5 | C2—N4—C4 | 112.84 (12) |
H8'1—C8'—H8'2 | 109.5 | C2—N4—H4 | 123.6 |
C7'—C8'—H8'3 | 109.5 | C4—N4—H4 | 123.6 |
H8'1—C8'—H8'3 | 109.5 | C5—O4—C6 | 117.28 (14) |
H8'2—C8'—H8'3 | 109.5 | C9—O6—C10 | 117.51 (14) |
N3—C3—C4—N1 | 133.40 (12) | O1—C1—N1—C4 | −176.74 (14) |
N2—C3—C4—N1 | 13.43 (14) | N2—C1—N1—C4 | 2.66 (18) |
C5—C3—C4—N1 | −104.61 (14) | N4—C4—N1—C1 | 98.59 (15) |
N3—C3—C4—N4 | 13.91 (14) | C9—C4—N1—C1 | −137.38 (13) |
N2—C3—C4—N4 | −106.06 (12) | C3—C4—N1—C1 | −10.49 (16) |
C5—C3—C4—N4 | 135.91 (13) | O1—C1—N2—C3 | −173.07 (14) |
N3—C3—C4—C9 | −104.09 (14) | N1—C1—N2—C3 | 7.54 (17) |
N2—C3—C4—C9 | 135.94 (13) | N3—C3—N2—C1 | −123.43 (14) |
C5—C3—C4—C9 | 17.90 (19) | C5—C3—N2—C1 | 111.10 (14) |
N3—C3—C5—O3 | −30.6 (2) | C4—C3—N2—C1 | −13.12 (16) |
N2—C3—C5—O3 | 97.77 (18) | O2—C2—N3—C3 | −179.24 (15) |
C4—C3—C5—O3 | −148.60 (16) | N4—C2—N3—C3 | 0.77 (18) |
N3—C3—C5—O4 | 152.17 (13) | N2—C3—N3—C2 | 99.33 (15) |
N2—C3—C5—O4 | −79.41 (15) | C5—C3—N3—C2 | −136.16 (13) |
C4—C3—C5—O4 | 34.22 (18) | C4—C3—N3—C2 | −9.65 (16) |
O4—C6—C7—C8 | 167.4 (6) | O2—C2—N4—C4 | −170.19 (15) |
C7'—C6—C7—C8 | −171 (5) | N3—C2—N4—C4 | 9.81 (18) |
O4—C6—C7'—C8' | 173.8 (12) | N1—C4—N4—C2 | −125.35 (14) |
C7—C6—C7'—C8' | 14 (4) | C9—C4—N4—C2 | 109.47 (14) |
N1—C4—C9—O5 | −12.1 (2) | C3—C4—N4—C2 | −14.86 (16) |
N4—C4—C9—O5 | 115.65 (18) | O3—C5—O4—C6 | −2.8 (3) |
C3—C4—C9—O5 | −130.59 (17) | C3—C5—O4—C6 | 174.24 (14) |
N1—C4—C9—O6 | 171.75 (13) | C7—C6—O4—C5 | 160.1 (5) |
N4—C4—C9—O6 | −60.55 (16) | C7'—C6—O4—C5 | 155.0 (9) |
C3—C4—C9—O6 | 53.21 (18) | O5—C9—O6—C10 | −2.8 (3) |
O6—C10—C11—C12 | 71.3 (6) | C4—C9—O6—C10 | 173.21 (15) |
C11'—C10—C11—C12 | −18.6 (5) | C11—C10—O6—C9 | −138.0 (2) |
C11—C10—C11'—C12' | 39.3 (7) | C11'—C10—O6—C9 | −96.0 (3) |
O6—C10—C11'—C12' | −64.4 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3i | 0.97 | 2.56 | 3.494 (3) | 163 |
N4—H4···O1ii | 0.86 | 2.09 | 2.8459 (16) | 146 |
N3—H3···O1iii | 0.86 | 2.20 | 3.0134 (17) | 157 |
N2—H2···O2iv | 0.86 | 2.09 | 2.9265 (16) | 163 |
N1—H1···O2v | 0.86 | 1.98 | 2.8320 (17) | 174 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y+1/2, z; (iii) x+1/2, y, −z+1/2; (iv) −x+2, y−1/2, −z+1/2; (v) x−1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H18N4O6 |
Mr | 314.30 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 300 |
a, b, c (Å) | 13.3013 (7), 11.5852 (6), 19.9867 (10) |
V (Å3) | 3079.9 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20966, 3752, 2887 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.152, 1.04 |
No. of reflections | 3752 |
No. of parameters | 241 |
No. of restraints | 45 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.25 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3i | 0.97 | 2.56 | 3.494 (3) | 162.7 |
N4—H4···O1ii | 0.86 | 2.09 | 2.8459 (16) | 145.9 |
N3—H3···O1iii | 0.86 | 2.20 | 3.0134 (17) | 156.9 |
N2—H2···O2iv | 0.86 | 2.09 | 2.9265 (16) | 162.6 |
N1—H1···O2v | 0.86 | 1.98 | 2.8320 (17) | 174.1 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+3/2, y+1/2, z; (iii) x+1/2, y, −z+1/2; (iv) −x+2, y−1/2, −z+1/2; (v) x−1/2, y, −z+1/2. |
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Glycoluril –C4H6N4O2– skeleton moiety of the title compound (scheme 1) is an important building block for both molecular and supramolecular chemistry. Its derivatives have been used as the basis for molecular capsules (Hof et al., 2002), molecular clips (Rowan et al., 1999), self-complementary facial amphiphiles (Isaacs & Witt, 2002), and the cucurbit[n]uril (CB[n]) family (Kim et al., 2000), and its utilization has been explored as a platform for studies of crystal engineering (Wang et al., 2006; Chen et al., 2007). Despite a variety of crystal structures reported for a number of its derivatives, relatively few crystal structures are known for glycoluril derivatives without N-substituents, which exhibit two different H-bonded types (scheme 2). The mode A have been found for (R = H) (Li et al., 1994), (R = CH3) (Himes et al., 1978), (R = Ph) (Wu et al., 2002), and so on, but the mode B, so far was only observed in the (R = Ph) (Moon et al., 2003). Herein, we report the crystal structure of the title compound with R = –COO–n-C3H7) (Fig. 1), which exhibits the scarce mode B of hydrogen bonding (scheme 2).
In the crystal structure, the two-dimension hydrogen bonding network, shown in Fig. 2, is based on the formation of eight-membered rings and ten-membered rings H-bonding motifs. This is fully according with the scarce mode B of hydrogen bonding (scheme 2). While the mode A, reported in the crystal structure of the (scheme 2, R = H, CH3, Ph), is only made up of eight-membered rings H-bonding motifs. In addition, intermolecular C10–H10B···O3 interactions (see table) can stabilize the crystal structure.