organic compounds
Dipropyl 4,8-dioxo-1H,5H-2,6-dioxa-3a,4a,7a,8a-tetraazacyclopenta[def]fluorene-8b,8c-dicarboxylate
aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: wsh2007@mails.ccnu.edu.cn
The title compound, C16H22N4O8, is a glycoluril derivative with two propoxycarbonyl substituents on the convex face of the glycoluril system. The dihedral angle between the five-membered rings in the glycoluril unit is 72.70 (2)°. The oxadiazinane six-membered ring displays a normal chair conformation. One of the propyl groups is disordered over two positions with site occupancies of 0.557 (7) and 0.443 (7). Intermolecular C—H⋯O hydrogen bonds are effective in the stabilization of the crystal structure.
Related literature
For related structures, see: Branda et al. (1995); Elemans et al. (1999); Gao & Sun (2007); Isaacs & Witt (2002); Isaacs et al. (1999); Li et al. (2007); Rebek (1999); Rowan et al. (1999); She & Xi (2007); Witt et al. (2000); Wu et al. (2002).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 2001); cell 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).
Supporting information
https://doi.org/10.1107/S1600536807065853/is2262sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065853/is2262Isup2.hkl
The title compound was synthesized according to the procedure reported (Isaacs et al., 1999). Crystals appropriate for X-ray data collection were obtained by slow evaporation of a dichloromethane solution at 283 K.
All H atoms were positioned geometrically, with C—H = 0.97 and 0.96 Å for methylene and methyl groups, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). One of the propyl groups is disordered over two positions and the final occupancies refined to 0.557 (7) and 0.443 (7). C15—C16 and C15'-C16' bond lengths were restrained to be 1.54 (1) Å, and C14—C15 and C14'-C15' to be 1.45 (1) Å. Same displacement parameters were used for atoms C15 and C15', and for atoms C16 and C16'. In the absence of significant
effects, Friedel pairs have been merged.Glycolurils are a topic of numerous reports; these compounds are of use in supramolecular chemistry as building blocks for molecular clips (Rowan et al., 1999; Isaacs & Witt, 2002) and molecular capsules (Rebek, 1999). The derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives and combinational chemistry (Witt et al., 2000). The widespread interest in glycolurils has led to a variety of crystal structures reported for a number of its derivatives. Here we report the structure of the title glycoluril derivative, (I) (Fig. 1), which is an important intermediate for the preparation glycoluril receptors (Wu et al., 2002) and in which the bond lengths and angles present no unusual features and are similar to those found in other similar compounds (Gao & Sun, 2007; She & Xi, 2007; Li et al., 2007).
The oxadiazinane six-membered ring displays a normal chair conformation. The weak intermolecular C—H···O hydrogen bonds cause the formation of a three-dimensional network structure (Fig. 2).
For related structures, see: Branda et al. (1995); Elemans et al. (1999); Gao & Sun (2007); Isaacs & Witt (2002); Isaacs et al. (1999); Li et al. (2007); Rebek (1999); Rowan et al. (1999); She & Xi (2007); Witt et al. (2000); Wu et al. (2002).
Data collection: SMART (Bruker, 2001); cell
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: SHELXTL (Bruker, 2001).C16H22N4O8 | F(000) = 840 |
Mr = 398.38 | Dx = 1.424 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3466 reflections |
a = 8.6399 (4) Å | θ = 2.5–21.5° |
b = 13.401 (7) Å | µ = 0.12 mm−1 |
c = 16.0445 (8) Å | T = 294 K |
V = 1857.7 (10) Å3 | Block, colorless |
Z = 4 | 0.20 × 0.10 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1967 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.0°, θmin = 2.5° |
φ and ω scans | h = −11→9 |
17272 measured reflections | k = −16→17 |
2315 independent reflections | l = −19→20 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2494P] where P = (Fo2 + 2Fc2)/3 |
2315 reflections | (Δ/σ)max = 0.002 |
263 parameters | Δρmax = 0.26 e Å−3 |
4 restraints | Δρmin = −0.18 e Å−3 |
C16H22N4O8 | V = 1857.7 (10) Å3 |
Mr = 398.38 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.6399 (4) Å | µ = 0.12 mm−1 |
b = 13.401 (7) Å | T = 294 K |
c = 16.0445 (8) Å | 0.20 × 0.10 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1967 reflections with I > 2σ(I) |
17272 measured reflections | Rint = 0.041 |
2315 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 4 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.26 e Å−3 |
2315 reflections | Δρmin = −0.18 e Å−3 |
263 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 | 0.4167 (4) | 0.2297 (2) | 0.2432 (2) | 0.0501 (8) | |
H1A | 0.3680 | 0.2906 | 0.2239 | 0.060* | |
H1B | 0.3651 | 0.1739 | 0.2165 | 0.060* | |
C2 | 0.4676 (4) | 0.1327 (2) | 0.3595 (2) | 0.0539 (9) | |
H2A | 0.4169 | 0.0760 | 0.3338 | 0.065* | |
H2B | 0.4532 | 0.1278 | 0.4193 | 0.065* | |
C3 | 0.6597 (3) | 0.31946 (18) | 0.22249 (17) | 0.0357 (6) | |
C4 | 0.7391 (4) | 0.1724 (2) | 0.3941 (2) | 0.0484 (8) | |
C5 | 0.9211 (4) | 0.3717 (2) | 0.2653 (3) | 0.0605 (10) | |
H5A | 1.0236 | 0.3599 | 0.2427 | 0.073* | |
H5B | 0.8884 | 0.4380 | 0.2487 | 0.073* | |
C6 | 0.9781 (5) | 0.2689 (3) | 0.3785 (3) | 0.0685 (11) | |
H6A | 0.9851 | 0.2662 | 0.4388 | 0.082* | |
H6B | 1.0804 | 0.2564 | 0.3559 | 0.082* | |
C7 | 0.6721 (3) | 0.14966 (18) | 0.25409 (16) | 0.0325 (6) | |
C8 | 0.6681 (3) | 0.05026 (18) | 0.20526 (17) | 0.0356 (6) | |
C9 | 0.5560 (5) | −0.0444 (2) | 0.0969 (2) | 0.0569 (9) | |
H9A | 0.5447 | −0.1000 | 0.1352 | 0.068* | |
H9B | 0.6490 | −0.0549 | 0.0642 | 0.068* | |
C10 | 0.4189 (6) | −0.0385 (3) | 0.0411 (3) | 0.0821 (13) | |
H10A | 0.3995 | −0.1045 | 0.0187 | 0.098* | |
H10B | 0.3299 | −0.0202 | 0.0746 | 0.098* | |
C11 | 0.4299 (8) | 0.0317 (5) | −0.0287 (4) | 0.116 (2) | |
H11A | 0.4263 | 0.0988 | −0.0080 | 0.174* | |
H11B | 0.3448 | 0.0209 | −0.0662 | 0.174* | |
H11C | 0.5256 | 0.0212 | −0.0578 | 0.174* | |
C12 | 0.8373 (3) | 0.19597 (19) | 0.26092 (18) | 0.0350 (6) | |
C13 | 0.9645 (4) | 0.1474 (2) | 0.2084 (2) | 0.0426 (7) | |
C14 | 1.0282 (6) | 0.1060 (3) | 0.0683 (3) | 0.0803 (14) | |
H14A | 1.0758 | 0.0455 | 0.0893 | 0.096* | 0.557 (7) |
H14B | 1.1091 | 0.1541 | 0.0566 | 0.096* | 0.557 (7) |
H14C | 1.0186 | 0.0339 | 0.0664 | 0.096* | 0.443 (7) |
H14D | 1.1337 | 0.1222 | 0.0838 | 0.096* | 0.443 (7) |
C15 | 0.9389 (12) | 0.0845 (6) | −0.0080 (5) | 0.094 (3) | 0.557 (7) |
H15A | 0.8691 | 0.0294 | 0.0033 | 0.113* | 0.557 (7) |
H15B | 1.0101 | 0.0630 | −0.0511 | 0.113* | 0.557 (7) |
C16 | 0.844 (2) | 0.1729 (11) | −0.0413 (12) | 0.130 (5) | 0.557 (7) |
H16A | 0.7547 | 0.1828 | −0.0065 | 0.194* | 0.557 (7) |
H16B | 0.8109 | 0.1589 | −0.0973 | 0.194* | 0.557 (7) |
H16C | 0.9064 | 0.2320 | −0.0410 | 0.194* | 0.557 (7) |
C15' | 0.9949 (14) | 0.1470 (8) | −0.0134 (5) | 0.094 (3) | 0.443 (7) |
H15C | 1.0705 | 0.1237 | −0.0537 | 0.113* | 0.443 (7) |
H15D | 0.9984 | 0.2193 | −0.0117 | 0.113* | 0.443 (7) |
C16' | 0.833 (2) | 0.1113 (16) | −0.0377 (16) | 0.130 (5) | 0.443 (7) |
H16D | 0.8219 | 0.0418 | −0.0245 | 0.194* | 0.443 (7) |
H16E | 0.8173 | 0.1209 | −0.0964 | 0.194* | 0.443 (7) |
H16F | 0.7566 | 0.1490 | −0.0074 | 0.194* | 0.443 (7) |
N1 | 0.5792 (3) | 0.23013 (15) | 0.21957 (15) | 0.0347 (5) | |
N2 | 0.6315 (3) | 0.13036 (17) | 0.34032 (15) | 0.0426 (6) | |
N3 | 0.8136 (3) | 0.29806 (16) | 0.23239 (16) | 0.0390 (6) | |
N4 | 0.8717 (3) | 0.1929 (2) | 0.34926 (16) | 0.0471 (6) | |
O1 | 0.3994 (3) | 0.22198 (15) | 0.33015 (16) | 0.0533 (6) | |
O2 | 0.9261 (3) | 0.36549 (18) | 0.35326 (18) | 0.0682 (7) | |
O3 | 0.6044 (3) | 0.40152 (14) | 0.21303 (15) | 0.0511 (6) | |
O4 | 0.7212 (4) | 0.1841 (2) | 0.46809 (15) | 0.0726 (8) | |
O5 | 0.7493 (3) | −0.01743 (15) | 0.22604 (17) | 0.0561 (6) | |
O6 | 0.5676 (3) | 0.05015 (13) | 0.14370 (13) | 0.0442 (5) | |
O7 | 1.0852 (3) | 0.11865 (18) | 0.23472 (19) | 0.0643 (7) | |
O8 | 0.9201 (3) | 0.14622 (19) | 0.12965 (14) | 0.0631 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0357 (17) | 0.0445 (16) | 0.070 (2) | 0.0030 (13) | −0.0040 (16) | −0.0090 (14) |
C2 | 0.058 (2) | 0.0406 (15) | 0.063 (2) | −0.0100 (15) | 0.0269 (18) | −0.0051 (14) |
C3 | 0.0426 (17) | 0.0291 (12) | 0.0355 (14) | 0.0015 (11) | 0.0017 (13) | 0.0004 (10) |
C4 | 0.066 (2) | 0.0432 (16) | 0.0356 (17) | 0.0154 (15) | −0.0011 (16) | 0.0018 (12) |
C5 | 0.046 (2) | 0.0427 (16) | 0.093 (3) | −0.0112 (14) | 0.003 (2) | −0.0124 (17) |
C6 | 0.054 (2) | 0.075 (2) | 0.076 (3) | 0.0048 (19) | −0.026 (2) | −0.023 (2) |
C7 | 0.0319 (15) | 0.0294 (12) | 0.0362 (14) | 0.0018 (10) | 0.0036 (12) | −0.0029 (10) |
C8 | 0.0348 (15) | 0.0306 (12) | 0.0413 (16) | 0.0015 (11) | 0.0051 (13) | −0.0027 (11) |
C9 | 0.076 (3) | 0.0388 (15) | 0.056 (2) | −0.0057 (17) | 0.0001 (19) | −0.0154 (14) |
C10 | 0.076 (3) | 0.081 (3) | 0.089 (3) | −0.009 (2) | −0.007 (3) | −0.036 (2) |
C11 | 0.133 (5) | 0.117 (4) | 0.099 (4) | 0.021 (4) | −0.035 (4) | −0.004 (3) |
C12 | 0.0306 (15) | 0.0321 (12) | 0.0421 (15) | 0.0002 (11) | −0.0016 (12) | −0.0021 (11) |
C13 | 0.0306 (16) | 0.0367 (13) | 0.060 (2) | 0.0026 (12) | 0.0053 (14) | −0.0013 (13) |
C14 | 0.085 (3) | 0.081 (3) | 0.075 (3) | 0.026 (2) | 0.043 (3) | −0.002 (2) |
C15 | 0.126 (7) | 0.078 (5) | 0.079 (5) | −0.022 (4) | 0.064 (5) | −0.015 (4) |
C16 | 0.151 (8) | 0.170 (15) | 0.068 (4) | 0.011 (13) | 0.023 (5) | −0.002 (12) |
C15' | 0.126 (7) | 0.078 (5) | 0.079 (5) | −0.022 (4) | 0.064 (5) | −0.015 (4) |
C16' | 0.151 (8) | 0.170 (15) | 0.068 (4) | 0.011 (13) | 0.023 (5) | −0.002 (12) |
N1 | 0.0300 (12) | 0.0312 (10) | 0.0429 (13) | 0.0033 (9) | −0.0012 (11) | −0.0021 (9) |
N2 | 0.0523 (16) | 0.0358 (11) | 0.0397 (13) | −0.0004 (11) | 0.0086 (12) | 0.0027 (10) |
N3 | 0.0336 (13) | 0.0293 (10) | 0.0542 (14) | −0.0028 (9) | 0.0012 (11) | −0.0011 (10) |
N4 | 0.0431 (15) | 0.0521 (14) | 0.0461 (15) | 0.0096 (12) | −0.0126 (13) | −0.0050 (12) |
O1 | 0.0414 (13) | 0.0464 (11) | 0.0721 (16) | −0.0010 (10) | 0.0205 (11) | −0.0158 (10) |
O2 | 0.0538 (16) | 0.0610 (14) | 0.0899 (19) | −0.0064 (12) | −0.0132 (15) | −0.0325 (13) |
O3 | 0.0548 (15) | 0.0308 (9) | 0.0676 (14) | 0.0080 (9) | −0.0019 (12) | 0.0057 (9) |
O4 | 0.098 (2) | 0.0832 (17) | 0.0361 (13) | 0.0226 (17) | −0.0014 (14) | 0.0007 (12) |
O5 | 0.0535 (13) | 0.0359 (10) | 0.0788 (16) | 0.0124 (10) | −0.0078 (13) | −0.0107 (10) |
O6 | 0.0537 (13) | 0.0353 (9) | 0.0435 (11) | −0.0003 (9) | −0.0031 (11) | −0.0082 (8) |
O7 | 0.0360 (14) | 0.0604 (14) | 0.0966 (19) | 0.0096 (11) | −0.0057 (14) | −0.0154 (13) |
O8 | 0.0587 (16) | 0.0793 (16) | 0.0515 (14) | 0.0268 (13) | 0.0173 (13) | −0.0024 (12) |
C1—O1 | 1.407 (4) | C9—H9B | 0.9700 |
C1—N1 | 1.454 (4) | C10—C11 | 1.467 (7) |
C1—H1A | 0.9700 | C10—H10A | 0.9700 |
C1—H1B | 0.9700 | C10—H10B | 0.9700 |
C2—O1 | 1.414 (4) | C11—H11A | 0.9600 |
C2—N2 | 1.449 (4) | C11—H11B | 0.9600 |
C2—H2A | 0.9700 | C11—H11C | 0.9600 |
C2—H2B | 0.9700 | C12—N4 | 1.449 (4) |
C3—O3 | 1.209 (3) | C12—N3 | 1.457 (3) |
C3—N3 | 1.369 (4) | C12—C13 | 1.530 (4) |
C3—N1 | 1.385 (3) | C13—O7 | 1.189 (4) |
C4—O4 | 1.207 (4) | C13—O8 | 1.321 (4) |
C4—N4 | 1.381 (5) | C14—C15' | 1.450 (8) |
C4—N2 | 1.388 (4) | C14—O8 | 1.460 (4) |
C5—O2 | 1.414 (5) | C14—C15 | 1.475 (8) |
C5—N3 | 1.455 (4) | C14—H14A | 0.9700 |
C5—H5A | 0.9700 | C14—H14B | 0.9700 |
C5—H5B | 0.9700 | C14—H14C | 0.9700 |
C6—O2 | 1.429 (5) | C14—H14D | 0.9700 |
C6—N4 | 1.450 (4) | C15—C16 | 1.538 (9) |
C6—H6A | 0.9700 | C15—H15A | 0.9700 |
C6—H6B | 0.9700 | C15—H15B | 0.9700 |
C7—N2 | 1.451 (4) | C16—H16A | 0.9600 |
C7—N1 | 1.454 (3) | C16—H16B | 0.9600 |
C7—C8 | 1.546 (3) | C16—H16C | 0.9600 |
C7—C12 | 1.561 (4) | C15'—C16' | 1.532 (10) |
C8—O5 | 1.194 (3) | C15'—H15C | 0.9700 |
C8—O6 | 1.315 (3) | C15'—H15D | 0.9700 |
C9—O6 | 1.477 (3) | C16'—H16D | 0.9600 |
C9—C10 | 1.486 (6) | C16'—H16E | 0.9600 |
C9—H9A | 0.9700 | C16'—H16F | 0.9600 |
O1—C1—N1 | 111.2 (3) | N3—C12—C13 | 109.1 (2) |
O1—C1—H1A | 109.4 | N4—C12—C7 | 104.2 (2) |
N1—C1—H1A | 109.4 | N3—C12—C7 | 102.9 (2) |
O1—C1—H1B | 109.4 | C13—C12—C7 | 116.7 (2) |
N1—C1—H1B | 109.4 | O7—C13—O8 | 126.1 (3) |
H1A—C1—H1B | 108.0 | O7—C13—C12 | 124.9 (3) |
O1—C2—N2 | 110.8 (3) | O8—C13—C12 | 108.9 (3) |
O1—C2—H2A | 109.5 | C15'—C14—O8 | 110.1 (5) |
N2—C2—H2A | 109.5 | O8—C14—C15 | 107.3 (5) |
O1—C2—H2B | 109.5 | C15'—C14—H14A | 135.6 |
N2—C2—H2B | 109.5 | O8—C14—H14A | 110.3 |
H2A—C2—H2B | 108.1 | C15—C14—H14A | 110.3 |
O3—C3—N3 | 126.1 (3) | C15'—C14—H14B | 73.5 |
O3—C3—N1 | 125.7 (3) | O8—C14—H14B | 110.3 |
N3—C3—N1 | 108.1 (2) | C15—C14—H14B | 110.3 |
O4—C4—N4 | 126.4 (4) | H14A—C14—H14B | 108.5 |
O4—C4—N2 | 125.3 (4) | C15'—C14—H14C | 109.4 |
N4—C4—N2 | 108.2 (3) | O8—C14—H14C | 109.5 |
O2—C5—N3 | 110.0 (3) | C15'—C14—H14D | 109.4 |
O2—C5—H5A | 109.7 | O8—C14—H14D | 110.2 |
N3—C5—H5A | 109.7 | H14C—C14—H14D | 108.1 |
O2—C5—H5B | 109.7 | C14—C15—C16 | 114.7 (9) |
N3—C5—H5B | 109.7 | C16—C15—H14C | 148.2 |
H5A—C5—H5B | 108.2 | C14—C15—H15A | 108.6 |
O2—C6—N4 | 110.2 (3) | C16—C15—H15A | 108.6 |
O2—C6—H6A | 109.6 | H14C—C15—H15A | 78.3 |
N4—C6—H6A | 109.6 | C14—C15—H15B | 108.6 |
O2—C6—H6B | 109.6 | C16—C15—H15B | 108.6 |
N4—C6—H6B | 109.6 | H14C—C15—H15B | 98.0 |
H6A—C6—H6B | 108.1 | H15A—C15—H15B | 107.6 |
N2—C7—N1 | 111.2 (2) | C14—C15'—C16' | 107.1 (12) |
N2—C7—C8 | 108.9 (2) | C14—C15'—H15C | 110.3 |
N1—C7—C8 | 115.7 (2) | C16'—C15'—H15C | 110.3 |
N2—C7—C12 | 103.0 (2) | C14—C15'—H15D | 110.3 |
N1—C7—C12 | 103.7 (2) | C16'—C15'—H15D | 110.3 |
C8—C7—C12 | 113.5 (2) | H15C—C15'—H15D | 108.6 |
O5—C8—O6 | 126.6 (2) | C15'—C16'—H16D | 109.5 |
O5—C8—C7 | 120.0 (3) | C15'—C16'—H16E | 109.5 |
O6—C8—C7 | 113.3 (2) | H16D—C16'—H16E | 109.5 |
O6—C9—C10 | 108.3 (3) | C15'—C16'—H16F | 109.5 |
O6—C9—H9A | 110.0 | H16D—C16'—H16F | 109.5 |
C10—C9—H9A | 110.0 | H16E—C16'—H16F | 109.5 |
O6—C9—H9B | 110.0 | C3—N1—C1 | 118.7 (2) |
C10—C9—H9B | 110.0 | C3—N1—C7 | 110.5 (2) |
H9A—C9—H9B | 108.4 | C1—N1—C7 | 115.5 (2) |
C11—C10—C9 | 116.3 (4) | C4—N2—C2 | 120.9 (3) |
C11—C10—H10A | 108.2 | C4—N2—C7 | 111.0 (2) |
C9—C10—H10A | 108.2 | C2—N2—C7 | 115.8 (3) |
C11—C10—H10B | 108.2 | C3—N3—C5 | 121.3 (2) |
C9—C10—H10B | 108.2 | C3—N3—C12 | 111.7 (2) |
H10A—C10—H10B | 107.4 | C5—N3—C12 | 115.7 (2) |
C10—C11—H11A | 109.5 | C4—N4—C12 | 110.2 (3) |
C10—C11—H11B | 109.5 | C4—N4—C6 | 119.8 (3) |
H11A—C11—H11B | 109.5 | C12—N4—C6 | 115.3 (3) |
C10—C11—H11C | 109.5 | C1—O1—C2 | 110.4 (2) |
H11A—C11—H11C | 109.5 | C5—O2—C6 | 110.2 (3) |
H11B—C11—H11C | 109.5 | C8—O6—C9 | 115.3 (2) |
N4—C12—N3 | 111.3 (2) | C13—O8—C14 | 117.6 (3) |
N4—C12—C13 | 112.3 (2) | ||
N2—C7—C8—O5 | −59.0 (4) | O1—C2—N2—C7 | −51.7 (3) |
N1—C7—C8—O5 | 174.8 (3) | N1—C7—N2—C4 | −101.6 (3) |
C12—C7—C8—O5 | 55.1 (4) | C8—C7—N2—C4 | 129.7 (2) |
N2—C7—C8—O6 | 119.5 (3) | C12—C7—N2—C4 | 8.9 (3) |
N1—C7—C8—O6 | −6.6 (3) | N1—C7—N2—C2 | 41.1 (3) |
C12—C7—C8—O6 | −126.4 (3) | C8—C7—N2—C2 | −87.6 (3) |
O6—C9—C10—C11 | 69.0 (5) | C12—C7—N2—C2 | 151.7 (2) |
N2—C7—C12—N4 | 2.4 (2) | O3—C3—N3—C5 | 25.0 (5) |
N1—C7—C12—N4 | 118.5 (2) | N1—C3—N3—C5 | −158.9 (3) |
C8—C7—C12—N4 | −115.2 (2) | O3—C3—N3—C12 | 167.0 (3) |
N2—C7—C12—N3 | −113.8 (2) | N1—C3—N3—C12 | −17.0 (3) |
N1—C7—C12—N3 | 2.3 (3) | O2—C5—N3—C3 | 88.6 (3) |
C8—C7—C12—N3 | 128.6 (2) | O2—C5—N3—C12 | −52.0 (4) |
N2—C7—C12—C13 | 126.8 (2) | N4—C12—N3—C3 | −102.3 (3) |
N1—C7—C12—C13 | −117.1 (2) | C13—C12—N3—C3 | 133.3 (3) |
C8—C7—C12—C13 | 9.2 (3) | C7—C12—N3—C3 | 8.7 (3) |
N4—C12—C13—O7 | −6.8 (4) | N4—C12—N3—C5 | 42.0 (4) |
N3—C12—C13—O7 | 117.0 (3) | C13—C12—N3—C5 | −82.4 (3) |
C7—C12—C13—O7 | −127.0 (3) | C7—C12—N3—C5 | 153.0 (3) |
N4—C12—C13—O8 | 175.3 (2) | O4—C4—N4—C12 | −164.3 (3) |
N3—C12—C13—O8 | −60.8 (3) | N2—C4—N4—C12 | 19.2 (3) |
C7—C12—C13—O8 | 55.1 (3) | O4—C4—N4—C6 | −27.0 (5) |
C15'—C14—C15—C16 | −47.2 (12) | N2—C4—N4—C6 | 156.5 (3) |
O8—C14—C15—C16 | 53.5 (10) | N3—C12—N4—C4 | 97.1 (3) |
O8—C14—C15'—C16' | −63.6 (12) | C13—C12—N4—C4 | −140.3 (2) |
C15—C14—C15'—C16' | 29.3 (12) | C7—C12—N4—C4 | −13.1 (3) |
O3—C3—N1—C1 | −28.7 (4) | N3—C12—N4—C6 | −42.3 (4) |
N3—C3—N1—C1 | 155.2 (3) | C13—C12—N4—C6 | 80.3 (3) |
O3—C3—N1—C7 | −165.5 (3) | C7—C12—N4—C6 | −152.5 (3) |
N3—C3—N1—C7 | 18.4 (3) | O2—C6—N4—C4 | −82.6 (4) |
O1—C1—N1—C3 | −83.7 (3) | O2—C6—N4—C12 | 52.7 (4) |
O1—C1—N1—C7 | 51.1 (3) | N1—C1—O1—C2 | −60.0 (3) |
N2—C7—N1—C3 | 97.6 (3) | N2—C2—O1—C1 | 60.1 (4) |
C8—C7—N1—C3 | −137.4 (2) | N3—C5—O2—C6 | 60.9 (4) |
C12—C7—N1—C3 | −12.4 (3) | N4—C6—O2—C5 | −61.5 (4) |
N2—C7—N1—C1 | −40.6 (3) | O5—C8—O6—C9 | 0.3 (4) |
C8—C7—N1—C1 | 84.4 (3) | C7—C8—O6—C9 | −178.1 (3) |
C12—C7—N1—C1 | −150.7 (2) | C10—C9—O6—C8 | 169.5 (3) |
O4—C4—N2—C2 | 25.2 (5) | O7—C13—O8—C14 | 0.0 (5) |
N4—C4—N2—C2 | −158.2 (3) | C12—C13—O8—C14 | 177.8 (3) |
O4—C4—N2—C7 | 165.8 (3) | C15'—C14—O8—C13 | −155.8 (6) |
N4—C4—N2—C7 | −17.6 (3) | C15—C14—O8—C13 | 163.3 (4) |
O1—C2—N2—C4 | 87.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O2i | 0.97 | 2.58 | 3.482 (5) | 155 |
C9—H9B···O4ii | 0.97 | 2.58 | 3.388 (4) | 141 |
C5—H5B···O7iii | 0.97 | 2.45 | 3.310 (4) | 148 |
C9—H9A···O1iv | 0.97 | 2.50 | 3.364 (4) | 149 |
C2—H2A···O3iv | 0.97 | 2.46 | 3.368 (4) | 155 |
C1—H1B···O7v | 0.97 | 2.55 | 3.231 (4) | 128 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+3/2, −y, z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H22N4O8 |
Mr | 398.38 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 8.6399 (4), 13.401 (7), 16.0445 (8) |
V (Å3) | 1857.7 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17272, 2315, 1967 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.123, 1.07 |
No. of reflections | 2315 |
No. of parameters | 263 |
No. of restraints | 4 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O2i | 0.97 | 2.58 | 3.482 (5) | 155 |
C9—H9B···O4ii | 0.97 | 2.58 | 3.388 (4) | 141 |
C5—H5B···O7iii | 0.97 | 2.45 | 3.310 (4) | 148 |
C9—H9A···O1iv | 0.97 | 2.50 | 3.364 (4) | 149 |
C2—H2A···O3iv | 0.97 | 2.46 | 3.368 (4) | 155 |
C1—H1B···O7v | 0.97 | 2.55 | 3.231 (4) | 128 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+3/2, −y, z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x−1, y, z. |
Acknowledgements
The authors thank Dr She Neng-Fang and Meng Xiang-Gao for the data collection.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Glycolurils are a topic of numerous reports; these compounds are of use in supramolecular chemistry as building blocks for molecular clips (Rowan et al., 1999; Isaacs & Witt, 2002) and molecular capsules (Rebek, 1999). The derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives and combinational chemistry (Witt et al., 2000). The widespread interest in glycolurils has led to a variety of crystal structures reported for a number of its derivatives. Here we report the structure of the title glycoluril derivative, (I) (Fig. 1), which is an important intermediate for the preparation glycoluril receptors (Wu et al., 2002) and in which the bond lengths and angles present no unusual features and are similar to those found in other similar compounds (Gao & Sun, 2007; She & Xi, 2007; Li et al., 2007).
The oxadiazinane six-membered ring displays a normal chair conformation. The weak intermolecular C—H···O hydrogen bonds cause the formation of a three-dimensional network structure (Fig. 2).