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In the title glycoluril derivative, C18H28N6O8, the N-Ccarbonyl bond distances are much shorter than the other N-C bond distances in the same five-membered ring, indicating electron delocalization within the nearly planar ring. Both six-membered rings display chair conformations.
Supporting information
CCDC reference: 287763
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.155
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N6 - C16 .. 7.33 su
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.44
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 6.30 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
4 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
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
2-Aminoethanol (0.61 g, 10 mmol) and formaldehyde (1.2 g, 40 mmol) were added to a stirred solution of 2,5-dioxotetrahydroimidazo[4,5-d]imidazole-3a,6a-dicarboxylic acid diethyl ester (1.43 g, 5 mmol) in acetonitrile (50 ml) under a nitrogen atmosphere. The mixture was stirred overnight at room temperature. The solvent was evaporated to dryness and the compound was purified by column chromatography to yield solid (I) (yield 2.05 g, 90%). Single crystals of (I) were obtained by recrystallization from an ethyl acetate solution at 283 K.
Hydroxyl H and methyl H atoms were placed in calculated positions, with C—H = 0.96 Å and O—H = 0.82 Å, and torsion angles were refined to fit the electron density, with Uiso(H) = 1.5Ueq(carrier). Methylene H atoms were placed in calculated positions, with C—H = 0.97 Å, and refined in riding mode, with Uiso(H) = 1.5Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Diethyl 2,6-bis(2-hydroxyethyl)-4,8-dioxo-1,2,5,6-tetrahydrohydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate
top
Crystal data top
C18H28N6O8 | F(000) = 968 |
Mr = 456.46 | Dx = 1.408 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3098 reflections |
a = 10.116 (2) Å | θ = 2.5–24.7° |
b = 8.7131 (18) Å | µ = 0.11 mm−1 |
c = 24.608 (5) Å | T = 292 K |
β = 96.763 (4)° | Block, colourless |
V = 2153.9 (8) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2819 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ϕ and ω scans | h = −12→10 |
10431 measured reflections | k = −10→9 |
3758 independent reflections | l = −28→29 |
Refinement top
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0816P)2 + 0.5776P] where P = (Fo2 + 2Fc2)/3 |
3758 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.44 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C18H28N6O8 | V = 2153.9 (8) Å3 |
Mr = 456.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.116 (2) Å | µ = 0.11 mm−1 |
b = 8.7131 (18) Å | T = 292 K |
c = 24.608 (5) Å | 0.30 × 0.20 × 0.20 mm |
β = 96.763 (4)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2819 reflections with I > 2σ(I) |
10431 measured reflections | Rint = 0.029 |
3758 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | 2 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.44 e Å−3 |
3758 reflections | Δρmin = −0.18 e Å−3 |
293 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1712 (3) | 0.7538 (4) | −0.05670 (11) | 0.0701 (8) | |
H1A | 0.2060 | 0.8467 | −0.0714 | 0.084* | |
H1B | 0.2447 | 0.6826 | −0.0490 | 0.084* | |
C2 | 0.1176 (3) | 0.7924 (3) | −0.00373 (9) | 0.0581 (7) | |
H2A | 0.1873 | 0.8427 | 0.0203 | 0.070* | |
H2B | 0.0451 | 0.8649 | −0.0114 | 0.070* | |
C3 | 0.1705 (3) | 0.5495 (3) | 0.04421 (10) | 0.0562 (6) | |
H3A | 0.2225 | 0.5247 | 0.0147 | 0.067* | |
H3B | 0.1277 | 0.4561 | 0.0545 | 0.067* | |
C4 | −0.0034 (2) | 0.7035 (3) | 0.06972 (10) | 0.0542 (6) | |
H4A | −0.0517 | 0.6147 | 0.0806 | 0.065* | |
H4B | −0.0681 | 0.7817 | 0.0571 | 0.065* | |
C5 | 0.3771 (2) | 0.6813 (3) | 0.08723 (9) | 0.0495 (6) | |
C6 | 0.1180 (2) | 0.9150 (3) | 0.12333 (8) | 0.0471 (5) | |
C7 | 0.1957 (2) | 0.6647 (2) | 0.13687 (8) | 0.0426 (5) | |
C8 | 0.1554 (2) | 0.5311 (3) | 0.17244 (9) | 0.0524 (6) | |
C9 | 0.0393 (3) | 0.4654 (5) | 0.24753 (15) | 0.0930 (11) | |
H9A | −0.0356 | 0.5055 | 0.2643 | 0.112* | |
H9B | 0.0092 | 0.3752 | 0.2265 | 0.112* | |
C10 | 0.1451 (4) | 0.4214 (5) | 0.29034 (15) | 0.1140 (14) | |
H10A | 0.2175 | 0.3765 | 0.2739 | 0.171* | |
H10B | 0.1113 | 0.3481 | 0.3143 | 0.171* | |
H10C | 0.1762 | 0.5106 | 0.3109 | 0.171* | |
C11 | 0.2998 (2) | 0.7802 (2) | 0.16574 (8) | 0.0421 (5) | |
C12 | 0.3461 (2) | 0.7456 (3) | 0.22666 (9) | 0.0491 (6) | |
C13 | 0.3589 (4) | 0.8438 (4) | 0.31719 (11) | 0.0970 (12) | |
H13A | 0.3154 | 0.7599 | 0.3339 | 0.116* | |
H13B | 0.4541 | 0.8251 | 0.3219 | 0.116* | |
C14 | 0.3299 (4) | 0.9872 (4) | 0.34256 (12) | 0.0930 (11) | |
H14A | 0.3690 | 1.0701 | 0.3243 | 0.140* | |
H14B | 0.3663 | 0.9856 | 0.3804 | 0.140* | |
H14C | 0.2353 | 1.0013 | 0.3399 | 0.140* | |
C15 | 0.5006 (3) | 0.8999 (3) | 0.13647 (11) | 0.0625 (7) | |
H15A | 0.5486 | 0.9075 | 0.1729 | 0.075* | |
H15B | 0.5655 | 0.8842 | 0.1110 | 0.075* | |
C16 | 0.3257 (3) | 1.0617 (3) | 0.15760 (10) | 0.0594 (7) | |
H16A | 0.2737 | 1.1513 | 0.1452 | 0.071* | |
H16B | 0.3644 | 1.0807 | 0.1950 | 0.071* | |
C17 | 0.3928 (3) | 1.0660 (3) | 0.06471 (10) | 0.0715 (8) | |
H17A | 0.4592 | 1.0199 | 0.0444 | 0.086* | |
H17B | 0.3091 | 1.0134 | 0.0542 | 0.086* | |
C18 | 0.3776 (4) | 1.2253 (4) | 0.04926 (12) | 0.0940 (11) | |
H18A | 0.3170 | 1.2743 | 0.0716 | 0.113* | |
H18B | 0.4632 | 1.2763 | 0.0563 | 0.113* | |
N1 | 0.0697 (2) | 0.6609 (2) | 0.02504 (7) | 0.0527 (5) | |
N2 | 0.26042 (18) | 0.6071 (2) | 0.09174 (7) | 0.0467 (5) | |
N3 | 0.08299 (17) | 0.7626 (2) | 0.11808 (7) | 0.0457 (5) | |
N4 | 0.41161 (17) | 0.7652 (2) | 0.13444 (7) | 0.0487 (5) | |
N5 | 0.23592 (19) | 0.9270 (2) | 0.15689 (7) | 0.0461 (5) | |
N6 | 0.4323 (2) | 1.0419 (3) | 0.12347 (8) | 0.0615 (6) | |
O1 | 0.0770 (2) | 0.6891 (2) | −0.09669 (8) | 0.0774 (6) | |
H1 | 0.0116 | 0.7452 | −0.1016 | 0.116* | |
O2 | 0.44246 (18) | 0.6696 (2) | 0.04907 (7) | 0.0704 (5) | |
O3 | 0.05176 (18) | 1.0217 (2) | 0.10359 (7) | 0.0644 (5) | |
O4 | 0.1849 (2) | 0.4015 (2) | 0.16575 (8) | 0.0857 (7) | |
O5 | 0.08462 (19) | 0.5820 (2) | 0.21051 (8) | 0.0693 (5) | |
O6 | 0.4078 (2) | 0.6334 (2) | 0.24048 (7) | 0.0734 (6) | |
O7 | 0.30995 (19) | 0.8540 (2) | 0.25888 (6) | 0.0672 (5) | |
O8 | 0.3283 (2) | 1.2432 (3) | −0.00666 (8) | 0.0882 (7) | |
H8 | 0.3906 | 1.2580 | −0.0245 | 0.132* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0688 (17) | 0.083 (2) | 0.0553 (15) | 0.0127 (15) | −0.0046 (13) | 0.0055 (14) |
C2 | 0.0680 (16) | 0.0560 (15) | 0.0451 (13) | −0.0020 (12) | −0.0154 (11) | −0.0024 (11) |
C3 | 0.0682 (15) | 0.0511 (14) | 0.0452 (12) | 0.0046 (12) | −0.0102 (11) | −0.0095 (11) |
C4 | 0.0480 (13) | 0.0595 (15) | 0.0511 (13) | −0.0001 (11) | −0.0104 (11) | −0.0008 (11) |
C5 | 0.0481 (13) | 0.0598 (15) | 0.0394 (12) | 0.0138 (11) | −0.0002 (10) | −0.0014 (10) |
C6 | 0.0565 (13) | 0.0479 (13) | 0.0353 (11) | 0.0146 (11) | −0.0020 (10) | 0.0002 (10) |
C7 | 0.0446 (12) | 0.0439 (12) | 0.0373 (11) | 0.0055 (9) | −0.0037 (9) | −0.0004 (9) |
C8 | 0.0540 (14) | 0.0509 (15) | 0.0488 (13) | 0.0005 (11) | −0.0086 (11) | 0.0032 (11) |
C9 | 0.075 (2) | 0.111 (3) | 0.096 (2) | −0.0091 (18) | 0.0224 (18) | 0.046 (2) |
C10 | 0.095 (3) | 0.154 (4) | 0.092 (3) | −0.018 (2) | 0.008 (2) | 0.055 (3) |
C11 | 0.0454 (12) | 0.0456 (12) | 0.0334 (10) | 0.0057 (9) | −0.0037 (9) | −0.0012 (9) |
C12 | 0.0503 (13) | 0.0543 (14) | 0.0403 (12) | 0.0065 (11) | −0.0052 (10) | 0.0018 (11) |
C13 | 0.146 (3) | 0.106 (3) | 0.0342 (14) | 0.033 (2) | −0.0096 (16) | −0.0045 (15) |
C14 | 0.120 (3) | 0.104 (3) | 0.0535 (16) | −0.037 (2) | 0.0037 (17) | −0.0130 (17) |
C15 | 0.0570 (15) | 0.0735 (18) | 0.0542 (15) | −0.0085 (13) | −0.0044 (12) | 0.0014 (13) |
C16 | 0.0789 (17) | 0.0463 (14) | 0.0484 (14) | 0.0014 (12) | −0.0121 (12) | −0.0062 (11) |
C17 | 0.093 (2) | 0.0702 (18) | 0.0502 (15) | −0.0149 (15) | 0.0022 (14) | 0.0004 (13) |
C18 | 0.145 (3) | 0.080 (2) | 0.0571 (18) | 0.006 (2) | 0.0127 (19) | 0.0136 (16) |
N1 | 0.0587 (12) | 0.0510 (12) | 0.0435 (10) | 0.0029 (9) | −0.0137 (9) | −0.0040 (9) |
N2 | 0.0505 (11) | 0.0491 (11) | 0.0383 (9) | 0.0084 (9) | −0.0040 (8) | −0.0061 (8) |
N3 | 0.0438 (10) | 0.0499 (11) | 0.0408 (10) | 0.0085 (8) | −0.0063 (8) | 0.0012 (8) |
N4 | 0.0450 (10) | 0.0575 (12) | 0.0421 (10) | 0.0005 (9) | −0.0018 (8) | −0.0010 (9) |
N5 | 0.0569 (11) | 0.0397 (10) | 0.0386 (10) | 0.0069 (8) | −0.0079 (8) | −0.0020 (8) |
N6 | 0.0718 (14) | 0.0635 (14) | 0.0475 (11) | −0.0106 (11) | −0.0003 (10) | −0.0011 (10) |
O1 | 0.1008 (16) | 0.0740 (13) | 0.0544 (11) | 0.0165 (11) | −0.0027 (10) | −0.0106 (9) |
O2 | 0.0622 (11) | 0.0981 (15) | 0.0525 (10) | 0.0105 (10) | 0.0139 (9) | −0.0104 (10) |
O3 | 0.0731 (11) | 0.0561 (10) | 0.0587 (10) | 0.0256 (9) | −0.0146 (9) | 0.0009 (8) |
O4 | 0.1329 (19) | 0.0482 (12) | 0.0751 (13) | 0.0083 (12) | 0.0083 (13) | 0.0072 (10) |
O5 | 0.0681 (11) | 0.0722 (12) | 0.0707 (12) | 0.0052 (9) | 0.0207 (10) | 0.0198 (10) |
O6 | 0.0928 (14) | 0.0739 (13) | 0.0486 (10) | 0.0328 (11) | −0.0123 (9) | 0.0055 (9) |
O7 | 0.0936 (13) | 0.0719 (12) | 0.0330 (8) | 0.0243 (10) | −0.0055 (8) | −0.0019 (8) |
O8 | 0.0856 (14) | 0.1176 (18) | 0.0608 (12) | 0.0031 (14) | 0.0058 (10) | 0.0254 (12) |
Geometric parameters (Å, º) top
C1—O1 | 1.404 (3) | C10—H10B | 0.9600 |
C1—C2 | 1.507 (4) | C10—H10C | 0.9600 |
C1—H1A | 0.9700 | C11—N4 | 1.448 (3) |
C1—H1B | 0.9700 | C11—N5 | 1.438 (3) |
C2—N1 | 1.459 (3) | C11—C12 | 1.547 (3) |
C2—H2A | 0.9700 | C12—O6 | 1.188 (3) |
C2—H2B | 0.9700 | C12—O7 | 1.312 (3) |
C3—N1 | 1.446 (3) | C13—C14 | 1.442 (5) |
C3—N2 | 1.482 (3) | C13—O7 | 1.464 (3) |
C3—H3A | 0.9700 | C13—H13A | 0.9700 |
C3—H3B | 0.9700 | C13—H13B | 0.9700 |
C4—N1 | 1.444 (3) | C14—H14A | 0.9600 |
C4—N3 | 1.483 (3) | C14—H14B | 0.9600 |
C4—H4A | 0.9700 | C14—H14C | 0.9600 |
C4—H4B | 0.9700 | C15—N6 | 1.435 (3) |
C5—O2 | 1.215 (3) | C15—N4 | 1.476 (3) |
C5—N2 | 1.362 (3) | C15—H15A | 0.9700 |
C5—N4 | 1.382 (3) | C15—H15B | 0.9700 |
C6—O3 | 1.214 (3) | C16—N6 | 1.453 (3) |
C6—N5 | 1.373 (3) | C16—N5 | 1.483 (3) |
C6—N3 | 1.377 (3) | C16—H16A | 0.9700 |
C7—N2 | 1.444 (3) | C16—H16B | 0.9700 |
C7—N3 | 1.455 (3) | C17—C18 | 1.443 (4) |
C7—C8 | 1.540 (3) | C17—N6 | 1.469 (3) |
C7—C11 | 1.565 (3) | C17—H17A | 0.9700 |
C8—O4 | 1.185 (3) | C17—H17B | 0.9700 |
C8—O5 | 1.321 (3) | C18—O8 | 1.416 (3) |
C9—C10 | 1.462 (5) | C18—H18A | 0.9700 |
C9—O5 | 1.474 (3) | C18—H18B | 0.9700 |
C9—H9A | 0.9700 | O1—H1 | 0.8200 |
C9—H9B | 0.9700 | O8—H8 | 0.8200 |
C10—H10A | 0.9600 | | |
| | | |
O1—C1—C2 | 114.4 (2) | O7—C12—C11 | 111.81 (19) |
O1—C1—H1A | 108.7 | C14—C13—O7 | 108.0 (3) |
C2—C1—H1A | 108.7 | C14—C13—H13A | 110.1 |
O1—C1—H1B | 108.7 | O7—C13—H13A | 110.1 |
C2—C1—H1B | 108.7 | C14—C13—H13B | 110.1 |
H1A—C1—H1B | 107.6 | O7—C13—H13B | 110.1 |
N1—C2—C1 | 114.7 (2) | H13A—C13—H13B | 108.4 |
N1—C2—H2A | 108.6 | C13—C14—H14A | 109.5 |
C1—C2—H2A | 108.6 | C13—C14—H14B | 109.5 |
N1—C2—H2B | 108.6 | H14A—C14—H14B | 109.5 |
C1—C2—H2B | 108.6 | C13—C14—H14C | 109.5 |
H2A—C2—H2B | 107.6 | H14A—C14—H14C | 109.5 |
N1—C3—N2 | 111.95 (18) | H14B—C14—H14C | 109.5 |
N1—C3—H3A | 109.2 | N6—C15—N4 | 113.7 (2) |
N2—C3—H3A | 109.2 | N6—C15—H15A | 108.8 |
N1—C3—H3B | 109.2 | N4—C15—H15A | 108.8 |
N2—C3—H3B | 109.2 | N6—C15—H15B | 108.8 |
H3A—C3—H3B | 107.9 | N4—C15—H15B | 108.8 |
N1—C4—N3 | 113.22 (18) | H15A—C15—H15B | 107.7 |
N1—C4—H4A | 108.9 | N6—C16—N5 | 113.22 (19) |
N3—C4—H4A | 108.9 | N6—C16—H16A | 108.9 |
N1—C4—H4B | 108.9 | N5—C16—H16A | 108.9 |
N3—C4—H4B | 108.9 | N6—C16—H16B | 108.9 |
H4A—C4—H4B | 107.7 | N5—C16—H16B | 108.9 |
O2—C5—N2 | 125.4 (2) | H16A—C16—H16B | 107.7 |
O2—C5—N4 | 126.0 (2) | C18—C17—N6 | 113.9 (2) |
N2—C5—N4 | 108.55 (19) | C18—C17—H17A | 108.8 |
O3—C6—N5 | 125.6 (2) | N6—C17—H17A | 108.8 |
O3—C6—N3 | 125.3 (2) | C18—C17—H17B | 108.8 |
N5—C6—N3 | 108.99 (17) | N6—C17—H17B | 108.8 |
N2—C7—N3 | 111.64 (16) | H17A—C17—H17B | 107.7 |
N2—C7—C8 | 110.41 (18) | O8—C18—C17 | 112.1 (3) |
N3—C7—C8 | 111.90 (18) | O8—C18—H18A | 109.2 |
N2—C7—C11 | 103.37 (17) | C17—C18—H18A | 109.2 |
N3—C7—C11 | 103.17 (16) | O8—C18—H18B | 109.2 |
C8—C7—C11 | 115.92 (16) | C17—C18—H18B | 109.2 |
O4—C8—O5 | 125.8 (2) | H18A—C18—H18B | 107.9 |
O4—C8—C7 | 123.6 (2) | C4—N1—C3 | 109.19 (18) |
O5—C8—C7 | 110.6 (2) | C4—N1—C2 | 113.37 (19) |
C10—C9—O5 | 111.8 (3) | C3—N1—C2 | 115.1 (2) |
C10—C9—H9A | 109.3 | C5—N2—C7 | 111.92 (18) |
O5—C9—H9A | 109.3 | C5—N2—C3 | 123.63 (19) |
C10—C9—H9B | 109.3 | C7—N2—C3 | 115.66 (18) |
O5—C9—H9B | 109.3 | C6—N3—C7 | 110.61 (17) |
H9A—C9—H9B | 107.9 | C6—N3—C4 | 122.04 (18) |
C9—C10—H10A | 109.5 | C7—N3—C4 | 114.67 (17) |
C9—C10—H10B | 109.5 | C5—N4—C11 | 111.04 (17) |
H10A—C10—H10B | 109.5 | C5—N4—C15 | 122.8 (2) |
C9—C10—H10C | 109.5 | C11—N4—C15 | 114.94 (19) |
H10A—C10—H10C | 109.5 | C6—N5—C11 | 111.50 (17) |
H10B—C10—H10C | 109.5 | C6—N5—C16 | 123.71 (18) |
N5—C11—N4 | 111.41 (18) | C11—N5—C16 | 116.02 (18) |
N5—C11—C12 | 113.55 (17) | C15—N6—C16 | 110.1 (2) |
N4—C11—C12 | 109.37 (17) | C15—N6—C17 | 114.3 (2) |
N5—C11—C7 | 103.71 (16) | C16—N6—C17 | 114.7 (2) |
N4—C11—C7 | 103.08 (16) | C1—O1—H1 | 109.5 |
C12—C11—C7 | 115.18 (18) | C8—O5—C9 | 116.1 (2) |
O6—C12—O7 | 126.4 (2) | C12—O7—C13 | 117.6 (2) |
O6—C12—C11 | 121.8 (2) | C18—O8—H8 | 109.5 |
| | | |
O1—C1—C2—N1 | 62.3 (3) | N2—C7—N3—C6 | −99.5 (2) |
N2—C7—C8—O4 | 6.2 (3) | C8—C7—N3—C6 | 136.23 (19) |
N3—C7—C8—O4 | 131.2 (2) | C11—C7—N3—C6 | 10.9 (2) |
C11—C7—C8—O4 | −110.9 (3) | N2—C7—N3—C4 | 43.4 (3) |
N2—C7—C8—O5 | −173.79 (18) | C8—C7—N3—C4 | −81.0 (2) |
N3—C7—C8—O5 | −48.8 (2) | C11—C7—N3—C4 | 153.74 (18) |
C11—C7—C8—O5 | 69.1 (2) | N1—C4—N3—C6 | 87.1 (3) |
N2—C7—C11—N5 | 113.33 (17) | N1—C4—N3—C7 | −51.0 (3) |
N3—C7—C11—N5 | −3.1 (2) | O2—C5—N4—C11 | 168.0 (2) |
C8—C7—C11—N5 | −125.74 (19) | N2—C5—N4—C11 | −15.2 (2) |
N2—C7—C11—N4 | −2.94 (19) | O2—C5—N4—C15 | 26.2 (3) |
N3—C7—C11—N4 | −119.35 (17) | N2—C5—N4—C15 | −156.9 (2) |
C8—C7—C11—N4 | 118.0 (2) | N5—C11—N4—C5 | −99.8 (2) |
N2—C7—C11—C12 | −121.98 (19) | C12—C11—N4—C5 | 133.88 (19) |
N3—C7—C11—C12 | 121.60 (19) | C7—C11—N4—C5 | 10.9 (2) |
C8—C7—C11—C12 | −1.1 (3) | N5—C11—N4—C15 | 45.2 (2) |
N5—C11—C12—O6 | −175.3 (2) | C12—C11—N4—C15 | −81.2 (2) |
N4—C11—C12—O6 | −50.1 (3) | C7—C11—N4—C15 | 155.84 (17) |
C7—C11—C12—O6 | 65.4 (3) | N6—C15—N4—C5 | 88.8 (3) |
N5—C11—C12—O7 | 4.1 (3) | N6—C15—N4—C11 | −51.7 (3) |
N4—C11—C12—O7 | 129.2 (2) | O3—C6—N5—C11 | −170.4 (2) |
C7—C11—C12—O7 | −115.3 (2) | N3—C6—N5—C11 | 13.0 (2) |
N6—C17—C18—O8 | −174.8 (3) | O3—C6—N5—C16 | −24.3 (4) |
N3—C4—N1—C3 | 56.0 (3) | N3—C6—N5—C16 | 159.0 (2) |
N3—C4—N1—C2 | −73.7 (2) | N4—C11—N5—C6 | 104.5 (2) |
N2—C3—N1—C4 | −56.1 (3) | C12—C11—N5—C6 | −131.4 (2) |
N2—C3—N1—C2 | 72.7 (3) | C7—C11—N5—C6 | −5.7 (2) |
C1—C2—N1—C4 | −169.0 (2) | N4—C11—N5—C16 | −44.3 (2) |
C1—C2—N1—C3 | 64.4 (3) | C12—C11—N5—C16 | 79.7 (2) |
O2—C5—N2—C7 | −170.0 (2) | C7—C11—N5—C16 | −154.58 (18) |
N4—C5—N2—C7 | 13.1 (2) | N6—C16—N5—C6 | −95.7 (3) |
O2—C5—N2—C3 | −24.1 (3) | N6—C16—N5—C11 | 49.0 (3) |
N4—C5—N2—C3 | 159.01 (19) | N4—C15—N6—C16 | 53.2 (3) |
N3—C7—N2—C5 | 104.3 (2) | N4—C15—N6—C17 | −77.6 (3) |
C8—C7—N2—C5 | −130.56 (19) | N5—C16—N6—C15 | −51.5 (3) |
C11—C7—N2—C5 | −6.0 (2) | N5—C16—N6—C17 | 79.1 (3) |
N3—C7—N2—C3 | −44.5 (2) | C18—C17—N6—C15 | −155.0 (3) |
C8—C7—N2—C3 | 80.6 (2) | C18—C17—N6—C16 | 76.5 (3) |
C11—C7—N2—C3 | −154.78 (18) | O4—C8—O5—C9 | −0.1 (4) |
N1—C3—N2—C5 | −92.4 (3) | C7—C8—O5—C9 | 180.0 (2) |
N1—C3—N2—C7 | 52.4 (3) | C10—C9—O5—C8 | 79.5 (4) |
O3—C6—N3—C7 | 168.2 (2) | O6—C12—O7—C13 | 5.4 (4) |
N5—C6—N3—C7 | −15.1 (2) | C11—C12—O7—C13 | −173.9 (3) |
O3—C6—N3—C4 | 28.6 (3) | C14—C13—O7—C12 | 168.8 (3) |
N5—C6—N3—C4 | −154.71 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.13 | 2.832 (3) | 144 |
O8—H8···O2ii | 0.82 | 1.96 | 2.760 (3) | 164 |
C16—H16A···O4iii | 0.97 | 2.43 | 3.302 (3) | 149 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) x, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C18H28N6O8 |
Mr | 456.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 10.116 (2), 8.7131 (18), 24.608 (5) |
β (°) | 96.763 (4) |
V (Å3) | 2153.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10431, 3758, 2819 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.155, 1.03 |
No. of reflections | 3758 |
No. of parameters | 293 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.18 |
Selected bond lengths (Å) topC1—O1 | 1.404 (3) | C8—O4 | 1.185 (3) |
C5—O2 | 1.215 (3) | C8—O5 | 1.321 (3) |
C5—N2 | 1.362 (3) | C9—O5 | 1.474 (3) |
C5—N4 | 1.382 (3) | C11—N4 | 1.448 (3) |
C6—O3 | 1.214 (3) | C11—N5 | 1.438 (3) |
C6—N5 | 1.373 (3) | C12—O6 | 1.188 (3) |
C6—N3 | 1.377 (3) | C12—O7 | 1.312 (3) |
C7—N2 | 1.444 (3) | C13—O7 | 1.464 (3) |
C7—N3 | 1.455 (3) | C18—O8 | 1.416 (3) |
C7—C11 | 1.565 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.13 | 2.832 (3) | 144 |
O8—H8···O2ii | 0.82 | 1.96 | 2.760 (3) | 164 |
C16—H16A···O4iii | 0.97 | 2.43 | 3.302 (3) | 149 |
Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1, −y+2, −z; (iii) x, y+1, z. |
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Glycoluril derivatives have shown applications in many fields, such as explosives, slow-release fertilizers, crosslinkers, iodogens, stabilisers of organic compounds against photodegradation and reagents in combinatorial chemistry (Wu et al., 2002). As a part of our ongoing investigation of glycoluril derivatives (Li & Wu, 2005), we present here the structure of the title compound, (I).
The molecular structure of (I) is shown in Fig. 1. Within the nearly planar five-membered ring, the N—Ccarbonyl bond distances are much shorter than the other N—C distances (Table 1). This is due to π–π conjugation. Both six-membered rings display chair conformations.
Classical O—H···O and weaker C—H···O intermolecular hydrogen bonds occur in the crystal structure of (I) (Table 2).