Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027741/jh6016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027741/jh6016Isup2.hkl |
CCDC reference: 281774
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- R factor = 0.065
- wR factor = 0.172
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.99 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N1 .. 6.99 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
1,2-Bis(chloromethyl)-4-nitrobenzene (1.1 g, 5 mmol), diethoxycarbonyl glycoluril (1.43 g, 5 mmol), formaldehyde (2.4 g, 40 mmol) and trifluoroacetic acid (30 ml) were used as starting materials to synthesize the title compound according to the literature (Wu et al., 2002). Crystals suitable for X-ray diffraction were grown by slow evaporation of the MeCN–MeOH(1:1) solutions for title compound at ambient conditions.
After their location on a different Fourier map, H atoms were placed in calculated positions and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, and Uiso = 1.2 − 1.5 Ueq(C).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. | |
Fig. 2. C—H···O intermolecular hydrogen-bonding (dashed lines). |
C20H21N5O9 | F(000) = 992 |
Mr = 475.42 | Dx = 1.467 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2ybc | Cell parameters from 3635 reflections |
a = 10.0454 (18) Å | θ = 2.2–25.1° |
b = 25.564 (5) Å | µ = 0.12 mm−1 |
c = 8.4997 (15) Å | T = 292 K |
β = 99.427 (3)° | Block, colorless |
V = 2153.2 (7) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4225 independent reflections |
Radiation source: fine-focus sealed tube | 3284 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −12→11 |
Tmin = 0.966, Tmax = 0.988 | k = −31→31 |
11538 measured reflections | l = −10→6 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0729P)2 + 1.0059P] where P = (Fo2 + 2Fc2)/3 |
4225 reflections | (Δ/σ)max = 0.001 |
309 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C20H21N5O9 | V = 2153.2 (7) Å3 |
Mr = 475.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.0454 (18) Å | µ = 0.12 mm−1 |
b = 25.564 (5) Å | T = 292 K |
c = 8.4997 (15) Å | 0.30 × 0.20 × 0.10 mm |
β = 99.427 (3)° |
Bruker SMART CCD area-detector diffractometer | 4225 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 3284 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.988 | Rint = 0.053 |
11538 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.48 e Å−3 |
4225 reflections | Δρmin = −0.32 e Å−3 |
309 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 | ||
C1 | 0.1389 (3) | 0.42010 (13) | 0.6095 (4) | 0.0617 (8) | |
C2 | 0.0849 (3) | 0.45554 (12) | 0.7083 (3) | 0.0556 (7) | |
H2 | 0.0287 | 0.4440 | 0.7779 | 0.067* | |
C3 | 0.2213 (3) | 0.43524 (15) | 0.5052 (4) | 0.0673 (9) | |
H3 | 0.2560 | 0.4109 | 0.4415 | 0.081* | |
C4 | 0.2513 (3) | 0.48671 (15) | 0.4970 (3) | 0.0627 (8) | |
H4 | 0.3065 | 0.4976 | 0.4254 | 0.075* | |
C5 | 0.2016 (3) | 0.52406 (12) | 0.5933 (3) | 0.0505 (7) | |
C6 | 0.1168 (2) | 0.50771 (11) | 0.7001 (3) | 0.0465 (6) | |
C7 | 0.0658 (2) | 0.54637 (11) | 0.8104 (3) | 0.0444 (6) | |
H7A | 0.0136 | 0.5733 | 0.7475 | 0.053* | |
H7B | 0.0065 | 0.5285 | 0.8722 | 0.053* | |
C8 | 0.2401 (3) | 0.58054 (13) | 0.5820 (3) | 0.0547 (7) | |
H8A | 0.2946 | 0.5842 | 0.4983 | 0.066* | |
H8B | 0.1588 | 0.6011 | 0.5516 | 0.066* | |
C9 | 0.2468 (2) | 0.54454 (10) | 1.0469 (3) | 0.0405 (6) | |
C10 | 0.4515 (2) | 0.59340 (10) | 0.7716 (3) | 0.0455 (6) | |
C11 | 0.2515 (2) | 0.61362 (10) | 0.8665 (3) | 0.0411 (6) | |
C12 | 0.1604 (2) | 0.66209 (11) | 0.8355 (3) | 0.0484 (6) | |
C13 | 0.0130 (3) | 0.71658 (13) | 0.9564 (5) | 0.0777 (10) | |
H13A | 0.0204 | 0.7328 | 1.0606 | 0.093* | |
H13B | 0.0363 | 0.7425 | 0.8822 | 0.093* | |
C14 | −0.1244 (4) | 0.6991 (2) | 0.9051 (8) | 0.1211 (19) | |
H14A | −0.1386 | 0.6925 | 0.7924 | 0.182* | |
H14B | −0.1859 | 0.7257 | 0.9281 | 0.182* | |
H14C | −0.1398 | 0.6676 | 0.9607 | 0.182* | |
C15 | 0.3742 (2) | 0.61854 (10) | 1.0053 (3) | 0.0412 (6) | |
C16 | 0.3883 (3) | 0.66993 (11) | 1.0983 (4) | 0.0517 (7) | |
C17 | 0.4105 (4) | 0.76209 (12) | 1.0753 (5) | 0.0721 (9) | |
H17A | 0.3635 | 0.7877 | 1.0022 | 0.087* | |
H17B | 0.3710 | 0.7626 | 1.1721 | 0.087* | |
C18 | 0.5533 (5) | 0.77571 (18) | 1.1127 (7) | 0.1125 (16) | |
H18A | 0.5975 | 0.7527 | 1.1942 | 0.169* | |
H18B | 0.5622 | 0.8112 | 1.1501 | 0.169* | |
H18C | 0.5939 | 0.7722 | 1.0187 | 0.169* | |
C19 | 0.4785 (3) | 0.55311 (12) | 1.2008 (3) | 0.0535 (7) | |
H19A | 0.5146 | 0.5773 | 1.2849 | 0.064* | |
H19B | 0.4564 | 0.5208 | 1.2503 | 0.064* | |
C20 | 0.6092 (2) | 0.58940 (11) | 1.0257 (4) | 0.0517 (7) | |
H20A | 0.6773 | 0.5816 | 0.9603 | 0.062* | |
H20B | 0.6463 | 0.6151 | 1.1049 | 0.062* | |
N1 | 0.1078 (4) | 0.36465 (13) | 0.6249 (5) | 0.0868 (9) | |
N2 | 0.17610 (19) | 0.57088 (8) | 0.9189 (2) | 0.0394 (5) | |
N3 | 0.3152 (2) | 0.60163 (9) | 0.7303 (2) | 0.0456 (5) | |
N4 | 0.35689 (19) | 0.57505 (9) | 1.1083 (3) | 0.0453 (5) | |
N5 | 0.49109 (19) | 0.61109 (8) | 0.9262 (3) | 0.0431 (5) | |
O1 | 0.0227 (5) | 0.35157 (13) | 0.6997 (5) | 0.1286 (13) | |
O2 | 0.1678 (5) | 0.33316 (15) | 0.5526 (7) | 0.168 (2) | |
O3 | 0.21406 (17) | 0.50392 (8) | 1.1014 (2) | 0.0533 (5) | |
O4 | 0.52464 (19) | 0.57600 (8) | 0.6843 (2) | 0.0578 (5) | |
O5 | 0.1399 (2) | 0.68482 (9) | 0.7114 (3) | 0.0756 (7) | |
O6 | 0.1065 (2) | 0.67258 (8) | 0.9643 (3) | 0.0603 (5) | |
O7 | 0.3960 (3) | 0.67188 (10) | 1.2402 (3) | 0.0871 (8) | |
O8 | 0.3943 (2) | 0.70982 (7) | 1.0026 (2) | 0.0593 (5) | |
O9 | 0.57720 (17) | 0.54315 (8) | 1.1034 (2) | 0.0537 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0488 (15) | 0.0693 (19) | 0.0590 (18) | 0.0059 (14) | −0.0147 (14) | −0.0124 (15) |
C2 | 0.0411 (14) | 0.0709 (19) | 0.0500 (16) | −0.0025 (13) | −0.0070 (12) | −0.0041 (14) |
C3 | 0.0532 (17) | 0.091 (3) | 0.0537 (19) | 0.0037 (16) | −0.0025 (15) | −0.0219 (17) |
C4 | 0.0463 (15) | 0.100 (3) | 0.0405 (15) | 0.0054 (16) | 0.0028 (12) | −0.0083 (15) |
C5 | 0.0358 (12) | 0.0801 (19) | 0.0332 (13) | 0.0054 (12) | −0.0012 (10) | 0.0027 (13) |
C6 | 0.0323 (12) | 0.0625 (16) | 0.0411 (14) | 0.0031 (11) | −0.0043 (10) | 0.0002 (12) |
C7 | 0.0298 (11) | 0.0593 (15) | 0.0437 (14) | 0.0008 (10) | 0.0052 (10) | 0.0048 (12) |
C8 | 0.0424 (14) | 0.086 (2) | 0.0362 (14) | 0.0067 (13) | 0.0079 (11) | 0.0110 (13) |
C9 | 0.0299 (11) | 0.0519 (14) | 0.0411 (13) | 0.0016 (10) | 0.0099 (10) | 0.0076 (11) |
C10 | 0.0372 (12) | 0.0510 (14) | 0.0503 (15) | 0.0018 (11) | 0.0131 (11) | 0.0135 (12) |
C11 | 0.0338 (12) | 0.0500 (14) | 0.0400 (13) | 0.0023 (10) | 0.0070 (10) | 0.0081 (11) |
C12 | 0.0356 (12) | 0.0526 (15) | 0.0566 (16) | 0.0032 (11) | 0.0064 (12) | 0.0154 (13) |
C13 | 0.069 (2) | 0.0600 (19) | 0.107 (3) | 0.0233 (16) | 0.021 (2) | 0.0001 (19) |
C14 | 0.061 (2) | 0.116 (4) | 0.181 (5) | 0.031 (2) | 0.003 (3) | −0.021 (4) |
C15 | 0.0317 (11) | 0.0492 (14) | 0.0429 (13) | 0.0023 (10) | 0.0069 (10) | 0.0078 (11) |
C16 | 0.0446 (14) | 0.0582 (17) | 0.0512 (16) | 0.0041 (12) | 0.0049 (12) | 0.0001 (13) |
C17 | 0.084 (2) | 0.0534 (17) | 0.082 (2) | 0.0051 (16) | 0.0249 (19) | −0.0084 (17) |
C18 | 0.097 (3) | 0.082 (3) | 0.157 (5) | −0.025 (2) | 0.015 (3) | −0.041 (3) |
C19 | 0.0384 (13) | 0.0655 (17) | 0.0533 (16) | −0.0003 (12) | −0.0021 (12) | 0.0179 (14) |
C20 | 0.0305 (12) | 0.0589 (16) | 0.0638 (17) | −0.0037 (11) | 0.0020 (12) | 0.0048 (14) |
N1 | 0.109 (2) | 0.079 (2) | 0.097 (2) | −0.0055 (18) | −0.0018 (18) | −0.0196 (19) |
N2 | 0.0319 (9) | 0.0472 (11) | 0.0390 (11) | 0.0008 (8) | 0.0055 (8) | 0.0055 (9) |
N3 | 0.0345 (10) | 0.0648 (14) | 0.0387 (11) | 0.0031 (9) | 0.0092 (9) | 0.0110 (10) |
N4 | 0.0326 (10) | 0.0574 (13) | 0.0446 (12) | −0.0020 (9) | 0.0027 (9) | 0.0144 (10) |
N5 | 0.0315 (10) | 0.0488 (12) | 0.0494 (12) | −0.0008 (8) | 0.0075 (9) | 0.0048 (10) |
O1 | 0.172 (4) | 0.086 (2) | 0.141 (3) | −0.020 (2) | 0.066 (3) | 0.000 (2) |
O2 | 0.185 (4) | 0.087 (2) | 0.256 (5) | −0.012 (2) | 0.104 (4) | −0.062 (3) |
O3 | 0.0387 (9) | 0.0638 (12) | 0.0582 (12) | −0.0047 (8) | 0.0106 (8) | 0.0200 (10) |
O4 | 0.0468 (10) | 0.0728 (13) | 0.0583 (12) | 0.0080 (9) | 0.0218 (9) | 0.0104 (10) |
O5 | 0.0767 (15) | 0.0760 (15) | 0.0739 (15) | 0.0234 (12) | 0.0121 (12) | 0.0326 (12) |
O6 | 0.0545 (11) | 0.0607 (12) | 0.0684 (13) | 0.0185 (9) | 0.0177 (10) | 0.0062 (10) |
O7 | 0.133 (2) | 0.0752 (16) | 0.0516 (14) | 0.0078 (15) | 0.0110 (14) | −0.0063 (11) |
O8 | 0.0702 (13) | 0.0468 (11) | 0.0612 (12) | −0.0047 (9) | 0.0116 (10) | −0.0004 (9) |
O9 | 0.0334 (9) | 0.0605 (11) | 0.0653 (12) | 0.0036 (8) | 0.0025 (8) | 0.0145 (10) |
C1—C3 | 1.364 (5) | C13—C14 | 1.448 (6) |
C1—C2 | 1.403 (4) | C13—O6 | 1.460 (3) |
C1—N1 | 1.462 (5) | C13—H13A | 0.9700 |
C2—C6 | 1.376 (4) | C13—H13B | 0.9700 |
C2—H2 | 0.9300 | C14—H14A | 0.9600 |
C3—C4 | 1.354 (5) | C14—H14B | 0.9600 |
C3—H3 | 0.9300 | C14—H14C | 0.9600 |
C4—C5 | 1.402 (4) | C15—N4 | 1.443 (3) |
C4—H4 | 0.9300 | C15—N5 | 1.458 (3) |
C5—C6 | 1.406 (4) | C15—C16 | 1.527 (4) |
C5—C8 | 1.502 (4) | C16—O7 | 1.197 (4) |
C6—C7 | 1.509 (4) | C16—O8 | 1.312 (3) |
C7—N2 | 1.461 (3) | C17—C18 | 1.460 (6) |
C7—H7A | 0.9700 | C17—O8 | 1.470 (4) |
C7—H7B | 0.9700 | C17—H17A | 0.9700 |
C8—N3 | 1.462 (4) | C17—H17B | 0.9700 |
C8—H8A | 0.9700 | C18—H18A | 0.9600 |
C8—H8B | 0.9700 | C18—H18B | 0.9600 |
C9—O3 | 1.205 (3) | C18—H18C | 0.9600 |
C9—N2 | 1.374 (3) | C19—O9 | 1.415 (3) |
C9—N4 | 1.384 (3) | C19—N4 | 1.452 (3) |
C10—O4 | 1.211 (3) | C19—H19A | 0.9700 |
C10—N3 | 1.372 (3) | C19—H19B | 0.9700 |
C10—N5 | 1.385 (3) | C20—O9 | 1.417 (3) |
C11—N2 | 1.441 (3) | C20—N5 | 1.450 (3) |
C11—N3 | 1.444 (3) | C20—H20A | 0.9700 |
C11—C12 | 1.538 (4) | C20—H20B | 0.9700 |
C11—C15 | 1.566 (3) | N1—O1 | 1.193 (4) |
C12—O5 | 1.192 (3) | N1—O2 | 1.229 (5) |
C12—O6 | 1.326 (3) | ||
C3—C1—C2 | 122.7 (3) | C13—C14—H14C | 109.5 |
C3—C1—N1 | 119.7 (3) | H14A—C14—H14C | 109.5 |
C2—C1—N1 | 117.6 (3) | H14B—C14—H14C | 109.5 |
C6—C2—C1 | 118.7 (3) | N4—C15—N5 | 111.5 (2) |
C6—C2—H2 | 120.7 | N4—C15—C16 | 111.0 (2) |
C1—C2—H2 | 120.7 | N5—C15—C16 | 109.7 (2) |
C4—C3—C1 | 118.2 (3) | N4—C15—C11 | 103.70 (19) |
C4—C3—H3 | 120.9 | N5—C15—C11 | 103.62 (19) |
C1—C3—H3 | 120.9 | C16—C15—C11 | 117.0 (2) |
C3—C4—C5 | 121.9 (3) | O7—C16—O8 | 126.2 (3) |
C3—C4—H4 | 119.1 | O7—C16—C15 | 122.8 (3) |
C5—C4—H4 | 119.1 | O8—C16—C15 | 111.0 (2) |
C4—C5—C6 | 119.1 (3) | C18—C17—O8 | 110.2 (3) |
C4—C5—C8 | 119.8 (3) | C18—C17—H17A | 109.6 |
C6—C5—C8 | 121.1 (3) | O8—C17—H17A | 109.6 |
C2—C6—C5 | 119.4 (3) | C18—C17—H17B | 109.6 |
C2—C6—C7 | 119.9 (3) | O8—C17—H17B | 109.6 |
C5—C6—C7 | 120.6 (3) | H17A—C17—H17B | 108.1 |
N2—C7—C6 | 111.93 (19) | C17—C18—H18A | 109.5 |
N2—C7—H7A | 109.2 | C17—C18—H18B | 109.5 |
C6—C7—H7A | 109.2 | H18A—C18—H18B | 109.5 |
N2—C7—H7B | 109.2 | C17—C18—H18C | 109.5 |
C6—C7—H7B | 109.2 | H18A—C18—H18C | 109.5 |
H7A—C7—H7B | 107.9 | H18B—C18—H18C | 109.5 |
N3—C8—C5 | 113.6 (2) | O9—C19—N4 | 111.2 (2) |
N3—C8—H8A | 108.8 | O9—C19—H19A | 109.4 |
C5—C8—H8A | 108.8 | N4—C19—H19A | 109.4 |
N3—C8—H8B | 108.8 | O9—C19—H19B | 109.4 |
C5—C8—H8B | 108.8 | N4—C19—H19B | 109.4 |
H8A—C8—H8B | 107.7 | H19A—C19—H19B | 108.0 |
O3—C9—N2 | 126.0 (2) | O9—C20—N5 | 111.40 (19) |
O3—C9—N4 | 126.3 (2) | O9—C20—H20A | 109.3 |
N2—C9—N4 | 107.5 (2) | N5—C20—H20A | 109.3 |
O4—C10—N3 | 125.4 (3) | O9—C20—H20B | 109.3 |
O4—C10—N5 | 126.3 (2) | N5—C20—H20B | 109.3 |
N3—C10—N5 | 108.2 (2) | H20A—C20—H20B | 108.0 |
N2—C11—N3 | 114.3 (2) | O1—N1—O2 | 122.4 (4) |
N2—C11—C12 | 109.61 (19) | O1—N1—C1 | 120.1 (4) |
N3—C11—C12 | 111.3 (2) | O2—N1—C1 | 117.4 (4) |
N2—C11—C15 | 102.53 (18) | C9—N2—C11 | 112.72 (19) |
N3—C11—C15 | 102.93 (18) | C9—N2—C7 | 122.0 (2) |
C12—C11—C15 | 116.0 (2) | C11—N2—C7 | 120.86 (19) |
O5—C12—O6 | 126.7 (3) | C10—N3—C11 | 112.5 (2) |
O5—C12—C11 | 123.8 (3) | C10—N3—C8 | 121.0 (2) |
O6—C12—C11 | 109.5 (2) | C11—N3—C8 | 122.4 (2) |
C14—C13—O6 | 110.5 (3) | C9—N4—C15 | 111.95 (19) |
C14—C13—H13A | 109.5 | C9—N4—C19 | 122.4 (2) |
O6—C13—H13A | 109.5 | C15—N4—C19 | 116.83 (19) |
C14—C13—H13B | 109.5 | C10—N5—C20 | 120.6 (2) |
O6—C13—H13B | 109.5 | C10—N5—C15 | 110.65 (19) |
H13A—C13—H13B | 108.1 | C20—N5—C15 | 115.1 (2) |
C13—C14—H14A | 109.5 | C12—O6—C13 | 117.7 (2) |
C13—C14—H14B | 109.5 | C16—O8—C17 | 117.4 (2) |
H14A—C14—H14B | 109.5 | C19—O9—C20 | 110.9 (2) |
C3—C1—C2—C6 | −0.3 (4) | N3—C11—N2—C7 | −57.7 (3) |
N1—C1—C2—C6 | 177.7 (2) | C12—C11—N2—C7 | 68.0 (3) |
C2—C1—C3—C4 | −0.2 (4) | C15—C11—N2—C7 | −168.3 (2) |
N1—C1—C3—C4 | −178.2 (3) | C6—C7—N2—C9 | −74.5 (3) |
C1—C3—C4—C5 | 0.8 (4) | C6—C7—N2—C11 | 80.2 (3) |
C3—C4—C5—C6 | −0.8 (4) | O4—C10—N3—C11 | 169.5 (2) |
C3—C4—C5—C8 | 178.8 (3) | N5—C10—N3—C11 | −13.8 (3) |
C1—C2—C6—C5 | 0.2 (4) | O4—C10—N3—C8 | 11.7 (4) |
C1—C2—C6—C7 | −177.0 (2) | N5—C10—N3—C8 | −171.6 (2) |
C4—C5—C6—C2 | 0.3 (4) | N2—C11—N3—C10 | −103.8 (2) |
C8—C5—C6—C2 | −179.3 (2) | C12—C11—N3—C10 | 131.4 (2) |
C4—C5—C6—C7 | 177.5 (2) | C15—C11—N3—C10 | 6.6 (3) |
C8—C5—C6—C7 | −2.1 (3) | N2—C11—N3—C8 | 53.6 (3) |
C2—C6—C7—N2 | 116.3 (3) | C12—C11—N3—C8 | −71.2 (3) |
C5—C6—C7—N2 | −60.9 (3) | C15—C11—N3—C8 | 164.0 (2) |
C4—C5—C8—N3 | −118.0 (3) | C5—C8—N3—C10 | 81.6 (3) |
C6—C5—C8—N3 | 61.6 (3) | C5—C8—N3—C11 | −73.9 (3) |
N2—C11—C12—O5 | −123.6 (3) | O3—C9—N4—C15 | 174.4 (2) |
N3—C11—C12—O5 | 3.8 (4) | N2—C9—N4—C15 | −9.9 (3) |
C15—C11—C12—O5 | 121.0 (3) | O3—C9—N4—C19 | 28.1 (4) |
N2—C11—C12—O6 | 54.1 (3) | N2—C9—N4—C19 | −156.1 (2) |
N3—C11—C12—O6 | −178.5 (2) | N5—C15—N4—C9 | −108.2 (2) |
C15—C11—C12—O6 | −61.3 (3) | C16—C15—N4—C9 | 129.1 (2) |
N2—C11—C15—N4 | 5.0 (2) | C11—C15—N4—C9 | 2.7 (3) |
N3—C11—C15—N4 | −113.9 (2) | N5—C15—N4—C19 | 40.1 (3) |
C12—C11—C15—N4 | 124.4 (2) | C16—C15—N4—C19 | −82.5 (3) |
N2—C11—C15—N5 | 121.5 (2) | C11—C15—N4—C19 | 151.0 (2) |
N3—C11—C15—N5 | 2.6 (2) | O9—C19—N4—C9 | 95.7 (3) |
C12—C11—C15—N5 | −119.1 (2) | O9—C19—N4—C15 | −49.1 (3) |
N2—C11—C15—C16 | −117.6 (2) | O4—C10—N5—C20 | −29.2 (4) |
N3—C11—C15—C16 | 123.5 (2) | N3—C10—N5—C20 | 154.1 (2) |
C12—C11—C15—C16 | 1.8 (3) | O4—C10—N5—C15 | −167.8 (3) |
N4—C15—C16—O7 | 6.3 (4) | N3—C10—N5—C15 | 15.5 (3) |
N5—C15—C16—O7 | −117.4 (3) | O9—C20—N5—C10 | −85.2 (3) |
C11—C15—C16—O7 | 125.0 (3) | O9—C20—N5—C15 | 51.7 (3) |
N4—C15—C16—O8 | −175.4 (2) | N4—C15—N5—C10 | 100.0 (2) |
N5—C15—C16—O8 | 60.9 (3) | C16—C15—N5—C10 | −136.6 (2) |
C11—C15—C16—O8 | −56.7 (3) | C11—C15—N5—C10 | −11.0 (3) |
C3—C1—N1—O1 | −170.3 (4) | N4—C15—N5—C20 | −41.1 (3) |
C2—C1—N1—O1 | 11.7 (5) | C16—C15—N5—C20 | 82.3 (3) |
C3—C1—N1—O2 | 6.5 (5) | C11—C15—N5—C20 | −152.0 (2) |
C2—C1—N1—O2 | −171.5 (4) | O5—C12—O6—C13 | −0.5 (4) |
O3—C9—N2—C11 | −170.6 (2) | C11—C12—O6—C13 | −178.1 (2) |
N4—C9—N2—C11 | 13.7 (3) | C14—C13—O6—C12 | 91.6 (4) |
O3—C9—N2—C7 | −14.1 (4) | O7—C16—O8—C17 | −0.7 (4) |
N4—C9—N2—C7 | 170.2 (2) | C15—C16—O8—C17 | −178.9 (2) |
N3—C11—N2—C9 | 99.1 (2) | C18—C17—O8—C16 | 92.4 (4) |
C12—C11—N2—C9 | −135.3 (2) | N4—C19—O9—C20 | 57.5 (3) |
C15—C11—N2—C9 | −11.5 (3) | N5—C20—O9—C19 | −59.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20A···O3i | 0.97 | 2.54 | 3.262 (4) | 132 |
C19—H19B···O4i | 0.97 | 2.54 | 3.444 (4) | 156 |
C17—H17A···O7ii | 0.97 | 2.52 | 3.293 (5) | 136 |
C7—H7B···O3iii | 0.97 | 2.41 | 3.288 (3) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H21N5O9 |
Mr | 475.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 10.0454 (18), 25.564 (5), 8.4997 (15) |
β (°) | 99.427 (3) |
V (Å3) | 2153.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.966, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11538, 4225, 3284 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.172, 1.05 |
No. of reflections | 4225 |
No. of parameters | 309 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.32 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
C1—N1 | 1.462 (5) | C11—N2 | 1.441 (3) |
C9—O3 | 1.205 (3) | C11—N3 | 1.444 (3) |
C9—N2 | 1.374 (3) | C11—C15 | 1.566 (3) |
C9—N4 | 1.384 (3) | C15—N4 | 1.443 (3) |
C10—O4 | 1.211 (3) | C15—N5 | 1.458 (3) |
C10—N3 | 1.372 (3) | C19—O9 | 1.415 (3) |
C10—N5 | 1.385 (3) | C20—O9 | 1.417 (3) |
N2—C7—C6 | 111.93 (19) | N2—C11—N3 | 114.3 (2) |
N3—C8—C5 | 113.6 (2) | N4—C15—N5 | 111.5 (2) |
N2—C9—N4 | 107.5 (2) | C19—O9—C20 | 110.9 (2) |
N3—C10—N5 | 108.2 (2) | ||
C6—C7—N2—C9 | −74.5 (3) | C5—C8—N3—C10 | 81.6 (3) |
C6—C7—N2—C11 | 80.2 (3) | C5—C8—N3—C11 | −73.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20A···O3i | 0.97 | 2.54 | 3.262 (4) | 132 |
C19—H19B···O4i | 0.97 | 2.54 | 3.444 (4) | 156 |
C17—H17A···O7ii | 0.97 | 2.52 | 3.293 (5) | 136 |
C7—H7B···O3iii | 0.97 | 2.41 | 3.288 (3) | 150 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+2. |
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The design and synthesis of host molecules for binding of neutral guest molecules continues to be an area of interest in supramolecular chemistry. In recent years, many molecular clips based on glycoluril and its derivatives have been studied, which can bind dihydroxy-substituted aromatic guests by means of hydrogen bonds as well as π-π interactions (Sijbesma & Notle, 1991; Reek et al., 1997; Rowan et al., 1999). In this paper, we report the crystal structure of the title compound (I) (Fig. 1), a new half molecular clip based on diethoxycarbonyl glycoluril. Selected bond lengths and angles are listed in Table 1. The crystal packing is mainly connected by intermolecular C—H···O interactions (Table 2 and Fig. 2).