The crystal structure of the title compound, C21H23N5O10, an important intermediate for molecular tweezers, shows intermolecular hydrogen bonding.
Supporting information
CCDC reference: 273829
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.135
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
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Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was synthesized according to the literature procedure of Wu, Chakraborty et al. (2002), using paraformaldehyde (0.18 g, 6 mmol), 2,3-bisbromomethyl-1-methoxy-4-nitrobenzene (4 mmol, 1.36 g) and glycoluril (5.72 g, 20 mmol) as starting materials. Crystals suitable for data collection were obtained by slow evaporation from methanol–1,2-dichloroethane (Ratio?) solution at 293 K.
All H atoms were initially located in a difference Fourier map. Methyl H atoms were then constrained to an ideal geometry, with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C). All other H atoms were placed in geometrically idealized positions, with C—H distances in the range 0.93–0.97 Å, and were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Diethyl 5,10-dihydro-9-methoxy-6-nitro-4,11-dioxo-
cis-1H,3
H,4H,11
H-2-oxa- 3a,4a,10
a,11
a-tetraazabenz[
f]indeno[2,1,7-ija]azulene-11
b,11
c-dicarboxylate
top
Crystal data top
C21H23N5O10 | Z = 2 |
Mr = 505.44 | F(000) = 528 |
Triclinic, P1 | Dx = 1.499 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.756 (2) Å | Cell parameters from 4159 reflections |
b = 10.608 (2) Å | θ = 2.6–28.3° |
c = 11.716 (3) Å | µ = 0.12 mm−1 |
α = 110.123 (4)° | T = 292 K |
β = 98.754 (4)° | Block, yellow |
γ = 92.119 (4)° | 0.30 × 0.20 × 0.20 mm |
V = 1119.9 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3412 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ϕ and ω scans | h = −12→12 |
8700 measured reflections | k = −13→13 |
4340 independent reflections | l = −14→14 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.073P)2 + 0.1853P] where P = (Fo2 + 2Fc2)/3 |
4340 reflections | (Δ/σ)max < 0.001 |
328 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Crystal data top
C21H23N5O10 | γ = 92.119 (4)° |
Mr = 505.44 | V = 1119.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.756 (2) Å | Mo Kα radiation |
b = 10.608 (2) Å | µ = 0.12 mm−1 |
c = 11.716 (3) Å | T = 292 K |
α = 110.123 (4)° | 0.30 × 0.20 × 0.20 mm |
β = 98.754 (4)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3412 reflections with I > 2σ(I) |
8700 measured reflections | Rint = 0.019 |
4340 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.26 e Å−3 |
4340 reflections | Δρmin = −0.17 e Å−3 |
328 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 | 0.6843 (3) | −0.2774 (2) | 0.4461 (2) | 0.0717 (7) | |
H1A | 0.7116 | −0.2796 | 0.5276 | 0.108* | |
H1B | 0.7015 | −0.3607 | 0.3862 | 0.108* | |
H1C | 0.5869 | −0.2654 | 0.4326 | 0.108* | |
C2 | 0.7505 (2) | −0.0408 (2) | 0.50995 (19) | 0.0472 (5) | |
C3 | 0.6793 (2) | −0.0129 (2) | 0.6080 (2) | 0.0591 (6) | |
H3 | 0.6339 | −0.0829 | 0.6228 | 0.071* | |
C4 | 0.6757 (2) | 0.1178 (2) | 0.6835 (2) | 0.0594 (6) | |
H4 | 0.6249 | 0.1373 | 0.7475 | 0.071* | |
C5 | 0.7479 (2) | 0.2202 (2) | 0.66358 (17) | 0.0486 (5) | |
C6 | 0.81973 (19) | 0.19730 (19) | 0.56482 (16) | 0.0412 (4) | |
C7 | 0.81672 (18) | 0.06393 (18) | 0.48470 (17) | 0.0404 (4) | |
C8 | 0.87676 (19) | 0.03312 (19) | 0.36697 (17) | 0.0417 (4) | |
H8A | 0.9741 | 0.0684 | 0.3878 | 0.050* | |
H8B | 0.8722 | −0.0639 | 0.3261 | 0.050* | |
C9 | 0.8897 (2) | 0.30903 (19) | 0.53468 (16) | 0.0434 (4) | |
H9A | 0.8947 | 0.3935 | 0.6033 | 0.052* | |
H9B | 0.9841 | 0.2895 | 0.5234 | 0.052* | |
C10 | 0.67423 (18) | 0.03475 (17) | 0.21357 (16) | 0.0379 (4) | |
C11 | 0.6829 (2) | 0.36657 (17) | 0.42607 (16) | 0.0390 (4) | |
C12 | 0.82507 (18) | 0.23392 (17) | 0.30060 (15) | 0.0354 (4) | |
C13 | 0.96537 (19) | 0.26171 (19) | 0.26505 (18) | 0.0433 (4) | |
C14 | 1.0811 (3) | 0.2167 (3) | 0.0922 (3) | 0.0732 (7) | |
H14A | 1.1550 | 0.1670 | 0.1156 | 0.088* | |
H14B | 1.1152 | 0.3114 | 0.1220 | 0.088* | |
C15 | 1.0384 (4) | 0.1660 (3) | −0.0441 (3) | 0.0982 (10) | |
H15A | 0.9939 | 0.0758 | −0.0716 | 0.147* | |
H15B | 1.1191 | 0.1659 | −0.0818 | 0.147* | |
H15C | 0.9745 | 0.2234 | −0.0671 | 0.147* | |
C16 | 0.69285 (18) | 0.25597 (17) | 0.21718 (15) | 0.0358 (4) | |
C17 | 0.7186 (2) | 0.31826 (19) | 0.12066 (17) | 0.0435 (4) | |
C18 | 0.8069 (3) | 0.5209 (3) | 0.1019 (3) | 0.0697 (7) | |
H18A | 0.8904 | 0.5827 | 0.1392 | 0.084* | |
H18B | 0.8189 | 0.4627 | 0.0203 | 0.084* | |
C19 | 0.6869 (3) | 0.5974 (3) | 0.0909 (3) | 0.0929 (9) | |
H19A | 0.6031 | 0.5369 | 0.0612 | 0.139* | |
H19B | 0.6970 | 0.6426 | 0.0339 | 0.139* | |
H19C | 0.6818 | 0.6628 | 0.1703 | 0.139* | |
C20 | 0.46796 (19) | 0.1200 (2) | 0.12854 (18) | 0.0470 (5) | |
H20A | 0.4446 | 0.1535 | 0.0614 | 0.056* | |
H20B | 0.4266 | 0.0276 | 0.1011 | 0.056* | |
C21 | 0.4703 (2) | 0.3364 (2) | 0.27194 (19) | 0.0483 (5) | |
H21A | 0.4307 | 0.3907 | 0.3419 | 0.058* | |
H21B | 0.4469 | 0.3713 | 0.2057 | 0.058* | |
N1 | 0.7426 (2) | 0.3560 (2) | 0.75081 (16) | 0.0600 (5) | |
N2 | 0.80236 (15) | 0.09153 (14) | 0.28193 (13) | 0.0360 (3) | |
N3 | 0.81338 (16) | 0.32315 (14) | 0.42234 (13) | 0.0387 (4) | |
N4 | 0.61829 (15) | 0.12341 (14) | 0.15920 (13) | 0.0379 (3) | |
N5 | 0.61892 (16) | 0.34618 (14) | 0.30650 (13) | 0.0384 (4) | |
O1 | 0.76296 (16) | −0.16808 (14) | 0.43397 (14) | 0.0594 (4) | |
O2 | 0.8501 (2) | 0.42990 (19) | 0.79215 (16) | 0.0834 (6) | |
O3 | 0.6308 (2) | 0.38728 (18) | 0.78133 (16) | 0.0791 (5) | |
O4 | 0.62129 (14) | −0.07552 (13) | 0.19868 (14) | 0.0545 (4) | |
O5 | 0.63453 (16) | 0.41730 (14) | 0.51834 (12) | 0.0541 (4) | |
O6 | 1.06315 (16) | 0.32901 (19) | 0.33582 (15) | 0.0732 (5) | |
O7 | 0.95947 (14) | 0.19839 (14) | 0.14557 (13) | 0.0517 (4) | |
O8 | 0.67792 (18) | 0.26598 (17) | 0.01277 (13) | 0.0667 (4) | |
O9 | 0.78743 (16) | 0.43882 (14) | 0.17747 (13) | 0.0563 (4) | |
O10 | 0.41237 (13) | 0.20003 (14) | 0.23236 (13) | 0.0502 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0908 (18) | 0.0483 (13) | 0.0754 (17) | −0.0123 (12) | 0.0087 (14) | 0.0254 (12) |
C2 | 0.0523 (11) | 0.0441 (11) | 0.0488 (11) | 0.0047 (9) | 0.0033 (9) | 0.0235 (9) |
C3 | 0.0711 (14) | 0.0567 (13) | 0.0599 (13) | 0.0001 (11) | 0.0184 (11) | 0.0313 (11) |
C4 | 0.0727 (15) | 0.0660 (15) | 0.0487 (12) | 0.0068 (11) | 0.0204 (11) | 0.0280 (11) |
C5 | 0.0590 (12) | 0.0511 (12) | 0.0350 (10) | 0.0070 (9) | 0.0036 (9) | 0.0163 (9) |
C6 | 0.0429 (10) | 0.0464 (11) | 0.0344 (10) | 0.0037 (8) | −0.0020 (7) | 0.0181 (8) |
C7 | 0.0411 (10) | 0.0432 (10) | 0.0399 (10) | 0.0071 (8) | 0.0025 (8) | 0.0198 (8) |
C8 | 0.0423 (10) | 0.0404 (10) | 0.0455 (11) | 0.0105 (8) | 0.0069 (8) | 0.0189 (8) |
C9 | 0.0503 (11) | 0.0412 (10) | 0.0345 (10) | −0.0008 (8) | −0.0008 (8) | 0.0123 (8) |
C10 | 0.0429 (10) | 0.0326 (9) | 0.0358 (9) | 0.0053 (7) | 0.0109 (7) | 0.0072 (7) |
C11 | 0.0548 (11) | 0.0279 (9) | 0.0343 (10) | 0.0074 (7) | 0.0090 (8) | 0.0102 (7) |
C12 | 0.0420 (10) | 0.0314 (9) | 0.0319 (9) | 0.0026 (7) | 0.0059 (7) | 0.0105 (7) |
C13 | 0.0432 (10) | 0.0429 (10) | 0.0452 (11) | −0.0006 (8) | 0.0053 (8) | 0.0190 (9) |
C14 | 0.0599 (14) | 0.0839 (17) | 0.0849 (18) | 0.0027 (12) | 0.0400 (13) | 0.0303 (15) |
C15 | 0.125 (3) | 0.094 (2) | 0.083 (2) | 0.0007 (18) | 0.0662 (19) | 0.0215 (17) |
C16 | 0.0433 (10) | 0.0332 (9) | 0.0308 (9) | 0.0066 (7) | 0.0085 (7) | 0.0102 (7) |
C17 | 0.0487 (11) | 0.0472 (11) | 0.0375 (11) | 0.0085 (8) | 0.0090 (8) | 0.0178 (9) |
C18 | 0.0809 (16) | 0.0751 (16) | 0.0756 (16) | 0.0021 (13) | 0.0198 (13) | 0.0528 (14) |
C19 | 0.124 (3) | 0.0777 (19) | 0.102 (2) | 0.0239 (17) | 0.0306 (19) | 0.0571 (18) |
C20 | 0.0418 (10) | 0.0498 (11) | 0.0437 (11) | 0.0072 (8) | 0.0019 (8) | 0.0114 (9) |
C21 | 0.0529 (12) | 0.0498 (12) | 0.0437 (11) | 0.0195 (9) | 0.0119 (9) | 0.0157 (9) |
N1 | 0.0848 (14) | 0.0602 (12) | 0.0363 (9) | 0.0071 (11) | 0.0101 (9) | 0.0188 (9) |
N2 | 0.0403 (8) | 0.0317 (8) | 0.0370 (8) | 0.0051 (6) | 0.0069 (6) | 0.0132 (6) |
N3 | 0.0477 (9) | 0.0353 (8) | 0.0312 (8) | 0.0038 (6) | 0.0032 (6) | 0.0112 (6) |
N4 | 0.0395 (8) | 0.0334 (8) | 0.0361 (8) | 0.0050 (6) | 0.0033 (6) | 0.0077 (6) |
N5 | 0.0487 (9) | 0.0360 (8) | 0.0314 (8) | 0.0128 (6) | 0.0093 (6) | 0.0113 (6) |
O1 | 0.0788 (10) | 0.0413 (8) | 0.0631 (10) | 0.0035 (7) | 0.0155 (8) | 0.0238 (7) |
O2 | 0.1094 (15) | 0.0730 (12) | 0.0498 (10) | −0.0157 (11) | 0.0104 (10) | 0.0029 (9) |
O3 | 0.1034 (14) | 0.0799 (12) | 0.0611 (11) | 0.0329 (10) | 0.0337 (10) | 0.0235 (9) |
O4 | 0.0571 (8) | 0.0344 (7) | 0.0666 (10) | −0.0032 (6) | 0.0017 (7) | 0.0155 (7) |
O5 | 0.0748 (10) | 0.0528 (8) | 0.0346 (7) | 0.0235 (7) | 0.0160 (7) | 0.0111 (6) |
O6 | 0.0548 (9) | 0.0950 (13) | 0.0601 (10) | −0.0241 (9) | 0.0021 (8) | 0.0217 (9) |
O7 | 0.0455 (7) | 0.0591 (9) | 0.0496 (8) | 0.0008 (6) | 0.0198 (6) | 0.0138 (7) |
O8 | 0.0872 (11) | 0.0786 (11) | 0.0331 (8) | −0.0012 (9) | 0.0054 (7) | 0.0215 (8) |
O9 | 0.0775 (10) | 0.0489 (8) | 0.0498 (9) | −0.0012 (7) | 0.0123 (7) | 0.0270 (7) |
O10 | 0.0431 (7) | 0.0566 (9) | 0.0509 (8) | 0.0106 (6) | 0.0120 (6) | 0.0170 (7) |
Geometric parameters (Å, º) top
C1—O1 | 1.426 (3) | C13—O6 | 1.187 (2) |
C1—H1A | 0.9600 | C13—O7 | 1.319 (2) |
C1—H1B | 0.9600 | C14—O7 | 1.459 (2) |
C1—H1C | 0.9600 | C14—C15 | 1.484 (4) |
C2—O1 | 1.359 (2) | C14—H14A | 0.9700 |
C2—C3 | 1.383 (3) | C14—H14B | 0.9700 |
C2—C7 | 1.404 (3) | C15—H15A | 0.9600 |
C3—C4 | 1.369 (3) | C15—H15B | 0.9600 |
C3—H3 | 0.9300 | C15—H15C | 0.9600 |
C4—C5 | 1.377 (3) | C16—N4 | 1.444 (2) |
C4—H4 | 0.9300 | C16—N5 | 1.457 (2) |
C5—C6 | 1.398 (3) | C16—C17 | 1.538 (2) |
C5—N1 | 1.460 (3) | C17—O8 | 1.188 (2) |
C6—C7 | 1.399 (3) | C17—O9 | 1.321 (2) |
C6—C9 | 1.515 (3) | C18—C19 | 1.463 (4) |
C7—C8 | 1.517 (3) | C18—O9 | 1.465 (2) |
C8—N2 | 1.463 (2) | C18—H18A | 0.9700 |
C8—H8A | 0.9700 | C18—H18B | 0.9700 |
C8—H8B | 0.9700 | C19—H19A | 0.9600 |
C9—N3 | 1.468 (2) | C19—H19B | 0.9600 |
C9—H9A | 0.9700 | C19—H19C | 0.9600 |
C9—H9B | 0.9700 | C20—O10 | 1.421 (2) |
C10—O4 | 1.205 (2) | C20—N4 | 1.452 (2) |
C10—N2 | 1.369 (2) | C20—H20A | 0.9700 |
C10—N4 | 1.390 (2) | C20—H20B | 0.9700 |
C11—O5 | 1.206 (2) | C21—O10 | 1.423 (2) |
C11—N3 | 1.372 (2) | C21—N5 | 1.435 (2) |
C11—N5 | 1.384 (2) | C21—H21A | 0.9700 |
C12—N3 | 1.439 (2) | C21—H21B | 0.9700 |
C12—N2 | 1.453 (2) | N1—O2 | 1.213 (3) |
C12—C13 | 1.537 (2) | N1—O3 | 1.221 (3) |
C12—C16 | 1.571 (2) | | |
| | | |
O1—C1—H1A | 109.5 | C14—C15—H15B | 109.5 |
O1—C1—H1B | 109.5 | H15A—C15—H15B | 109.5 |
H1A—C1—H1B | 109.5 | C14—C15—H15C | 109.5 |
O1—C1—H1C | 109.5 | H15A—C15—H15C | 109.5 |
H1A—C1—H1C | 109.5 | H15B—C15—H15C | 109.5 |
H1B—C1—H1C | 109.5 | N4—C16—N5 | 111.54 (14) |
O1—C2—C3 | 123.38 (18) | N4—C16—C17 | 111.24 (14) |
O1—C2—C7 | 115.93 (18) | N5—C16—C17 | 109.63 (14) |
C3—C2—C7 | 120.68 (19) | N4—C16—C12 | 104.10 (13) |
C4—C3—C2 | 120.0 (2) | N5—C16—C12 | 103.10 (13) |
C4—C3—H3 | 120.0 | C17—C16—C12 | 116.90 (14) |
C2—C3—H3 | 120.0 | O8—C17—O9 | 126.44 (18) |
C3—C4—C5 | 119.4 (2) | O8—C17—C16 | 124.30 (18) |
C3—C4—H4 | 120.3 | O9—C17—C16 | 109.22 (15) |
C5—C4—H4 | 120.3 | C19—C18—O9 | 110.8 (2) |
C4—C5—C6 | 122.67 (19) | C19—C18—H18A | 109.5 |
C4—C5—N1 | 115.84 (19) | O9—C18—H18A | 109.5 |
C6—C5—N1 | 121.47 (18) | C19—C18—H18B | 109.5 |
C5—C6—C7 | 117.35 (17) | O9—C18—H18B | 109.5 |
C5—C6—C9 | 123.66 (17) | H18A—C18—H18B | 108.1 |
C7—C6—C9 | 118.80 (16) | C18—C19—H19A | 109.5 |
C6—C7—C2 | 119.67 (17) | C18—C19—H19B | 109.5 |
C6—C7—C8 | 120.29 (16) | H19A—C19—H19B | 109.5 |
C2—C7—C8 | 119.94 (17) | C18—C19—H19C | 109.5 |
N2—C8—C7 | 112.31 (14) | H19A—C19—H19C | 109.5 |
N2—C8—H8A | 109.1 | H19B—C19—H19C | 109.5 |
C7—C8—H8A | 109.1 | O10—C20—N4 | 110.87 (15) |
N2—C8—H8B | 109.1 | O10—C20—H20A | 109.5 |
C7—C8—H8B | 109.1 | N4—C20—H20A | 109.5 |
H8A—C8—H8B | 107.9 | O10—C20—H20B | 109.5 |
N3—C9—C6 | 111.48 (14) | N4—C20—H20B | 109.5 |
N3—C9—H9A | 109.3 | H20A—C20—H20B | 108.1 |
C6—C9—H9A | 109.3 | O10—C21—N5 | 110.72 (14) |
N3—C9—H9B | 109.3 | O10—C21—H21A | 109.5 |
C6—C9—H9B | 109.3 | N5—C21—H21A | 109.5 |
H9A—C9—H9B | 108.0 | O10—C21—H21B | 109.5 |
O4—C10—N2 | 125.98 (17) | N5—C21—H21B | 109.5 |
O4—C10—N4 | 125.68 (17) | H21A—C21—H21B | 108.1 |
N2—C10—N4 | 108.27 (14) | O2—N1—O3 | 123.6 (2) |
O5—C11—N3 | 125.57 (17) | O2—N1—C5 | 118.3 (2) |
O5—C11—N5 | 126.22 (17) | O3—N1—C5 | 118.0 (2) |
N3—C11—N5 | 108.18 (15) | C10—N2—C12 | 112.36 (14) |
N3—C12—N2 | 114.23 (14) | C10—N2—C8 | 120.97 (14) |
N3—C12—C13 | 112.07 (14) | C12—N2—C8 | 121.83 (14) |
N2—C12—C13 | 109.38 (14) | C11—N3—C12 | 111.60 (14) |
N3—C12—C16 | 103.11 (13) | C11—N3—C9 | 117.68 (15) |
N2—C12—C16 | 102.39 (13) | C12—N3—C9 | 122.33 (15) |
C13—C12—C16 | 115.31 (14) | C10—N4—C16 | 110.76 (14) |
O6—C13—O7 | 126.17 (18) | C10—N4—C20 | 119.12 (15) |
O6—C13—C12 | 124.39 (18) | C16—N4—C20 | 115.74 (14) |
O7—C13—C12 | 109.44 (15) | C11—N5—C21 | 122.03 (15) |
O7—C14—C15 | 107.9 (2) | C11—N5—C16 | 110.98 (14) |
O7—C14—H14A | 110.1 | C21—N5—C16 | 116.37 (14) |
C15—C14—H14A | 110.1 | C2—O1—C1 | 118.21 (18) |
O7—C14—H14B | 110.1 | C13—O7—C14 | 118.00 (17) |
C15—C14—H14B | 110.1 | C17—O9—C18 | 117.11 (17) |
H14A—C14—H14B | 108.4 | C20—O10—C21 | 109.93 (14) |
C14—C15—H15A | 109.5 | | |
| | | |
O1—C2—C3—C4 | 177.5 (2) | C16—C12—N2—C10 | −6.52 (18) |
C7—C2—C3—C4 | −1.5 (3) | N3—C12—N2—C8 | −51.4 (2) |
C2—C3—C4—C5 | −2.6 (4) | C13—C12—N2—C8 | 75.16 (19) |
C3—C4—C5—C6 | 3.5 (3) | C16—C12—N2—C8 | −162.06 (14) |
C3—C4—C5—N1 | −177.9 (2) | C7—C8—N2—C10 | −75.8 (2) |
C4—C5—C6—C7 | −0.2 (3) | C7—C8—N2—C12 | 77.7 (2) |
N1—C5—C6—C7 | −178.78 (18) | O5—C11—N3—C12 | 163.25 (17) |
C4—C5—C6—C9 | 174.65 (19) | N5—C11—N3—C12 | −18.73 (19) |
N1—C5—C6—C9 | −3.9 (3) | O5—C11—N3—C9 | 14.2 (3) |
C5—C6—C7—C2 | −3.8 (3) | N5—C11—N3—C9 | −167.75 (14) |
C9—C6—C7—C2 | −178.99 (17) | N2—C12—N3—C11 | −95.88 (17) |
C5—C6—C7—C8 | 172.41 (17) | C13—C12—N3—C11 | 139.01 (15) |
C9—C6—C7—C8 | −2.8 (3) | C16—C12—N3—C11 | 14.39 (17) |
O1—C2—C7—C6 | −174.30 (16) | N2—C12—N3—C9 | 51.5 (2) |
C3—C2—C7—C6 | 4.8 (3) | C13—C12—N3—C9 | −73.64 (19) |
O1—C2—C7—C8 | 9.4 (3) | C16—C12—N3—C9 | 161.74 (14) |
C3—C2—C7—C8 | −171.46 (18) | C6—C9—N3—C11 | 66.5 (2) |
C6—C7—C8—N2 | −63.0 (2) | C6—C9—N3—C12 | −79.0 (2) |
C2—C7—C8—N2 | 113.21 (19) | O4—C10—N4—C16 | 167.50 (17) |
C5—C6—C9—N3 | −108.2 (2) | N2—C10—N4—C16 | −15.36 (18) |
C7—C6—C9—N3 | 66.6 (2) | O4—C10—N4—C20 | 29.5 (3) |
N3—C12—C13—O6 | 13.8 (3) | N2—C10—N4—C20 | −153.33 (15) |
N2—C12—C13—O6 | −113.9 (2) | N5—C16—N4—C10 | −99.68 (16) |
C16—C12—C13—O6 | 131.4 (2) | C17—C16—N4—C10 | 137.58 (15) |
N3—C12—C13—O7 | −166.84 (15) | C12—C16—N4—C10 | 10.84 (17) |
N2—C12—C13—O7 | 65.42 (18) | N5—C16—N4—C20 | 39.8 (2) |
C16—C12—C13—O7 | −49.3 (2) | C17—C16—N4—C20 | −82.92 (18) |
N3—C12—C16—N4 | −121.48 (13) | C12—C16—N4—C20 | 150.34 (14) |
N2—C12—C16—N4 | −2.63 (16) | O10—C20—N4—C10 | 84.80 (19) |
C13—C12—C16—N4 | 116.05 (15) | O10—C20—N4—C16 | −51.2 (2) |
N3—C12—C16—N5 | −4.92 (16) | O5—C11—N5—C21 | −23.8 (3) |
N2—C12—C16—N5 | 113.93 (14) | N3—C11—N5—C21 | 158.19 (15) |
C13—C12—C16—N5 | −127.39 (15) | O5—C11—N5—C16 | −167.04 (17) |
N3—C12—C16—C17 | 115.40 (16) | N3—C11—N5—C16 | 14.96 (19) |
N2—C12—C16—C17 | −125.75 (15) | O10—C21—N5—C11 | −90.42 (19) |
C13—C12—C16—C17 | −7.1 (2) | O10—C21—N5—C16 | 51.0 (2) |
N4—C16—C17—O8 | 2.5 (3) | N4—C16—N5—C11 | 105.40 (16) |
N5—C16—C17—O8 | −121.3 (2) | C17—C16—N5—C11 | −130.93 (15) |
C12—C16—C17—O8 | 121.9 (2) | C12—C16—N5—C11 | −5.74 (17) |
N4—C16—C17—O9 | −179.71 (15) | N4—C16—N5—C21 | −40.1 (2) |
N5—C16—C17—O9 | 56.45 (19) | C17—C16—N5—C21 | 83.56 (18) |
C12—C16—C17—O9 | −60.3 (2) | C12—C16—N5—C21 | −151.25 (15) |
C4—C5—N1—O2 | 135.0 (2) | C3—C2—O1—C1 | 8.2 (3) |
C6—C5—N1—O2 | −46.4 (3) | C7—C2—O1—C1 | −172.69 (19) |
C4—C5—N1—O3 | −42.5 (3) | O6—C13—O7—C14 | −3.2 (3) |
C6—C5—N1—O3 | 136.1 (2) | C12—C13—O7—C14 | 177.43 (18) |
O4—C10—N2—C12 | −169.24 (17) | C15—C14—O7—C13 | −166.0 (2) |
N4—C10—N2—C12 | 13.63 (19) | O8—C17—O9—C18 | 4.9 (3) |
O4—C10—N2—C8 | −13.5 (3) | C16—C17—O9—C18 | −172.78 (17) |
N4—C10—N2—C8 | 169.41 (14) | C19—C18—O9—C17 | 86.1 (3) |
N3—C12—N2—C10 | 104.18 (17) | N4—C20—O10—C21 | 60.3 (2) |
C13—C12—N2—C10 | −129.30 (15) | N5—C21—O10—C20 | −60.17 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O10i | 0.93 | 2.50 | 3.342 (3) | 150 |
C21—H21A···O5ii | 0.97 | 2.31 | 3.233 (2) | 158 |
C18—H18A···O2iii | 0.97 | 2.56 | 3.343 (3) | 138 |
C14—H14B···O2iii | 0.97 | 2.57 | 3.519 (3) | 167 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C21H23N5O10 |
Mr | 505.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 9.756 (2), 10.608 (2), 11.716 (3) |
α, β, γ (°) | 110.123 (4), 98.754 (4), 92.119 (4) |
V (Å3) | 1119.9 (4) |
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 CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8700, 4340, 3412 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.135, 1.06 |
No. of reflections | 4340 |
No. of parameters | 328 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.17 |
Selected geometric parameters (Å, º) topC2—C3 | 1.383 (3) | C10—N4 | 1.390 (2) |
C2—C7 | 1.404 (3) | C12—N2 | 1.453 (2) |
C7—C8 | 1.517 (3) | C12—C16 | 1.571 (2) |
C8—N2 | 1.463 (2) | C16—N4 | 1.444 (2) |
C10—O4 | 1.205 (2) | C20—N4 | 1.452 (2) |
C10—N2 | 1.369 (2) | C21—O10 | 1.423 (2) |
| | | |
C2—C7—C8 | 119.94 (17) | N2—C12—C16 | 102.39 (13) |
N2—C8—C7 | 112.31 (14) | O10—C20—N4 | 110.87 (15) |
N2—C10—N4 | 108.27 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O10i | 0.93 | 2.50 | 3.342 (3) | 150 |
C21—H21A···O5ii | 0.97 | 2.31 | 3.233 (2) | 158 |
C18—H18A···O2iii | 0.97 | 2.56 | 3.343 (3) | 138 |
C14—H14B···O2iii | 0.97 | 2.57 | 3.519 (3) | 167 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1. |
Derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives, slow-release fertilizers, crosslinkers, assessment of drug reactivity (Jeon et al., 2005), stabilization of organic compounds against photo-degradation and combinatorial chemistry (Wu, Fettinger & Isaacs, 2002; Wu, Chakraborty et al., 2002). The use of glycoluril derivatives as building blocks for self-assembly, molecular recognition (Kang & Kim, 2005) and catalysis in chloroform has been reported (Conn & Rebek, 1997). Many methylene-bridged glycoluril dimers have been synthesized from soluble organic diethoxycarbonyl glycoluril derivatives (Witt et al., 2000). In this paper, we present the X-ray crystal structure of the title compound (I).
The X-ray crystallographic structure of (I) is shown in Fig. 1. Selected bond distances and torsion angles describing the molecular conformation are listed in Table 1. The molecules are connected by intermolecular hydrogen bonding (Fig 2). In the crystal structure, the angle between the two five-membered rings of the glycoluril is 110°.