Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705458X/lh2535sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705458X/lh2535Isup2.hkl |
CCDC reference: 672818
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.053
- wR factor = 0.147
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C3 ... 1.44 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 5 Informative message, check
For related literature, see: Yin et al. (2006); Rebek (2005); Rowan et al. (1999); Witt et al. (2000).
The title compound was synthesized in analogy to the literature procedure of Yin et al. (2006), Crystals appropriate for data collection were obtained by slow evaporation from a methanol-chloroform solution (1:20 V/V) of (I).
The H atoms were constrained to an ideal geometry and constrained to ride on their parent atoms as follows: methylene H with d(C—H)=0.97 Å and Uiso(H) = 1.2Ueq(C); methine H with d(C—H)=0.98 Å and Uiso(H) = 1.2Ueq(C); aromatic H with d(C—H)=0.93 Å and Uiso(H) = 1.2Ueq(C). The unique ethyl acetate group is disorder over two sites; the site-occupancy factors for the two orientations were refined using the DFIX instruction in SHELXTL (Sheldrick, 2000) giving 0.539 (7) and 0.461 (7) for the major and minor components, respectively.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).
C30H28N6O6 | F(000) = 1192 |
Mr = 568.58 | Dx = 1.347 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3199 reflections |
a = 16.0226 (10) Å | θ = 2.2–22.7° |
b = 14.0617 (9) Å | µ = 0.10 mm−1 |
c = 13.7870 (9) Å | T = 294 K |
β = 115.523 (1)° | Plate, colorless |
V = 2803.1 (3) Å3 | 0.30 × 0.20 × 0.04 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 1952 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
/f and /w scans | h = −20→20 |
12898 measured reflections | k = −17→17 |
3057 independent reflections | l = −16→17 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0768P)2] where P = (Fo2 + 2Fc2)/3 |
3057 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.16 e Å−3 |
11 restraints | Δρmin = −0.18 e Å−3 |
C30H28N6O6 | V = 2803.1 (3) Å3 |
Mr = 568.58 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.0226 (10) Å | µ = 0.10 mm−1 |
b = 14.0617 (9) Å | T = 294 K |
c = 13.7870 (9) Å | 0.30 × 0.20 × 0.04 mm |
β = 115.523 (1)° |
Bruker SMART CCD area-detector diffractometer | 1952 reflections with I > 2σ(I) |
12898 measured reflections | Rint = 0.055 |
3057 independent reflections |
R[F2 > 2σ(F2)] = 0.053 | 11 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.16 e Å−3 |
3057 reflections | Δρmin = −0.18 e Å−3 |
229 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 | 0.1661 (2) | 1.5590 (2) | 0.3141 (2) | 0.1019 (9) | |
H1 | 0.1691 | 1.6246 | 0.3076 | 0.122* | |
C2 | 0.16248 (15) | 1.47641 (18) | 0.32223 (18) | 0.0773 (6) | |
C3 | 0.16116 (13) | 1.37528 (14) | 0.33657 (15) | 0.0638 (5) | |
C4 | 0.22584 (14) | 1.31674 (15) | 0.32419 (17) | 0.0687 (6) | |
H4 | 0.2685 | 1.3429 | 0.3027 | 0.082* | |
C5 | 0.22749 (13) | 1.22119 (14) | 0.34323 (17) | 0.0668 (5) | |
H5 | 0.2722 | 1.1837 | 0.3357 | 0.080* | |
C6 | 0.16372 (12) | 1.17853 (13) | 0.37371 (14) | 0.0581 (5) | |
C7 | 0.09803 (13) | 1.23665 (15) | 0.38301 (17) | 0.0692 (6) | |
H7 | 0.0535 | 1.2102 | 0.4013 | 0.083* | |
C8 | 0.09754 (14) | 1.33303 (16) | 0.36569 (18) | 0.0715 (6) | |
H8 | 0.0532 | 1.3707 | 0.3738 | 0.086* | |
C9 | 0.19180 (13) | 1.01352 (14) | 0.33255 (17) | 0.0676 (5) | |
H9A | 0.2329 | 0.9646 | 0.3778 | 0.081* | |
H9B | 0.2233 | 1.0459 | 0.2958 | 0.081* | |
C10 | 0.05180 (13) | 1.02199 (11) | 0.16204 (14) | 0.0521 (4) | |
C11 | −0.11956 (15) | 1.03730 (15) | 0.04899 (15) | 0.0683 (6) | |
H11A | −0.1018 | 1.0856 | 0.0112 | 0.082* | |
H11B | −0.1581 | 0.9911 | −0.0034 | 0.082* | |
C12 | −0.04897 (13) | 0.92670 (11) | 0.20293 (14) | 0.0525 (4) | |
C13 | −0.08516 (16) | 0.82917 (14) | 0.15162 (19) | 0.0730 (6) | |
N1 | 0.17227 (11) | 1.08128 (11) | 0.39963 (13) | 0.0654 (5) | |
N2 | 0.10735 (10) | 0.96859 (9) | 0.25254 (12) | 0.0535 (4) | |
N3 | −0.03683 (10) | 0.99023 (9) | 0.12713 (11) | 0.0528 (4) | |
O1 | 0.07893 (9) | 1.08330 (8) | 0.12080 (11) | 0.0660 (4) | |
C14 | −0.0932 (6) | 0.7206 (4) | 0.0159 (6) | 0.101 (2) | 0.539 (7) |
H14A | −0.1119 | 0.7359 | −0.0592 | 0.121* | 0.539 (7) |
H14B | −0.1472 | 0.6988 | 0.0242 | 0.121* | 0.539 (7) |
C15 | −0.0228 (4) | 0.6458 (4) | 0.0495 (6) | 0.118 (3) | 0.539 (7) |
H15A | 0.0320 | 0.6694 | 0.0460 | 0.176* | 0.539 (7) |
H15B | −0.0459 | 0.5920 | 0.0027 | 0.176* | 0.539 (7) |
H15C | −0.0085 | 0.6271 | 0.1219 | 0.176* | 0.539 (7) |
O2 | −0.0548 (5) | 0.8049 (4) | 0.0821 (6) | 0.107 (3) | 0.539 (7) |
O3 | −0.1358 (6) | 0.7852 (5) | 0.1785 (7) | 0.097 (2) | 0.539 (7) |
C14' | −0.0331 (5) | 0.6950 (4) | 0.0815 (5) | 0.0825 (19) | 0.461 (7) |
H14C | 0.0255 | 0.6739 | 0.0841 | 0.099* | 0.461 (7) |
H14D | −0.0503 | 0.6516 | 0.1245 | 0.099* | 0.461 (7) |
C15' | −0.1034 (6) | 0.6932 (6) | −0.0291 (5) | 0.097 (3) | 0.461 (7) |
H15D | −0.1621 | 0.7105 | −0.0312 | 0.145* | 0.461 (7) |
H15E | −0.1073 | 0.6304 | −0.0580 | 0.145* | 0.461 (7) |
H15F | −0.0873 | 0.7376 | −0.0712 | 0.145* | 0.461 (7) |
O2' | −0.0227 (4) | 0.7905 (4) | 0.1261 (6) | 0.084 (2) | 0.461 (7) |
O3' | −0.1586 (6) | 0.7929 (7) | 0.1352 (9) | 0.109 (4) | 0.461 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.127 (2) | 0.0702 (16) | 0.137 (2) | 0.0139 (15) | 0.085 (2) | 0.0180 (16) |
C2 | 0.0842 (14) | 0.0712 (16) | 0.0856 (16) | 0.0025 (12) | 0.0453 (13) | 0.0057 (12) |
C3 | 0.0683 (12) | 0.0612 (12) | 0.0584 (12) | −0.0044 (9) | 0.0239 (10) | 0.0000 (10) |
C4 | 0.0735 (12) | 0.0670 (13) | 0.0736 (14) | −0.0136 (10) | 0.0392 (11) | −0.0070 (10) |
C5 | 0.0659 (11) | 0.0654 (13) | 0.0750 (14) | −0.0075 (10) | 0.0360 (11) | −0.0087 (10) |
C6 | 0.0621 (11) | 0.0605 (12) | 0.0471 (11) | −0.0111 (9) | 0.0192 (9) | −0.0062 (9) |
C7 | 0.0709 (12) | 0.0709 (14) | 0.0740 (14) | −0.0071 (10) | 0.0390 (11) | −0.0002 (11) |
C8 | 0.0704 (12) | 0.0725 (14) | 0.0779 (14) | 0.0019 (10) | 0.0380 (12) | −0.0010 (11) |
C9 | 0.0668 (12) | 0.0601 (12) | 0.0805 (14) | 0.0043 (9) | 0.0362 (11) | 0.0062 (11) |
C10 | 0.0793 (12) | 0.0375 (9) | 0.0562 (11) | 0.0047 (8) | 0.0449 (10) | −0.0012 (8) |
C11 | 0.0872 (14) | 0.0668 (13) | 0.0500 (11) | 0.0066 (10) | 0.0287 (11) | −0.0030 (9) |
C12 | 0.0731 (10) | 0.0372 (9) | 0.0579 (11) | −0.0034 (8) | 0.0385 (9) | −0.0049 (7) |
C13 | 0.1027 (17) | 0.0463 (11) | 0.0882 (16) | −0.0129 (11) | 0.0583 (15) | −0.0129 (11) |
N1 | 0.0766 (10) | 0.0620 (10) | 0.0602 (10) | −0.0104 (8) | 0.0319 (9) | −0.0036 (8) |
N2 | 0.0677 (9) | 0.0414 (8) | 0.0615 (10) | 0.0025 (7) | 0.0375 (8) | 0.0033 (7) |
N3 | 0.0726 (10) | 0.0453 (8) | 0.0467 (8) | 0.0002 (7) | 0.0315 (8) | −0.0002 (6) |
O1 | 0.0950 (10) | 0.0526 (8) | 0.0732 (9) | 0.0010 (6) | 0.0577 (8) | 0.0087 (6) |
C14 | 0.153 (7) | 0.064 (4) | 0.090 (6) | −0.026 (4) | 0.057 (6) | −0.038 (4) |
C15 | 0.140 (5) | 0.085 (4) | 0.148 (6) | −0.007 (4) | 0.081 (5) | −0.030 (4) |
O2 | 0.190 (6) | 0.073 (3) | 0.103 (5) | −0.056 (4) | 0.106 (5) | −0.048 (3) |
O3 | 0.163 (5) | 0.051 (2) | 0.115 (6) | −0.044 (2) | 0.096 (4) | −0.038 (3) |
C14' | 0.111 (5) | 0.057 (4) | 0.086 (5) | −0.002 (4) | 0.048 (4) | −0.025 (3) |
C15' | 0.129 (6) | 0.078 (6) | 0.085 (5) | −0.032 (5) | 0.047 (4) | −0.023 (4) |
O2' | 0.125 (4) | 0.055 (2) | 0.094 (5) | −0.006 (2) | 0.069 (4) | −0.030 (3) |
O3' | 0.141 (5) | 0.101 (5) | 0.128 (8) | −0.063 (4) | 0.100 (6) | −0.057 (5) |
C1—C2 | 1.170 (3) | C12—N2i | 1.447 (2) |
C1—H1 | 0.9300 | C12—N3 | 1.450 (2) |
C2—C3 | 1.437 (3) | C12—C13 | 1.538 (3) |
C3—C8 | 1.381 (3) | C12—C12i | 1.547 (4) |
C3—C4 | 1.390 (3) | C13—O3 | 1.200 (5) |
C4—C5 | 1.367 (3) | C13—O3' | 1.211 (6) |
C4—H4 | 0.9300 | C13—O2 | 1.294 (4) |
C5—C6 | 1.397 (2) | C13—O2' | 1.314 (5) |
C5—H5 | 0.9300 | N1—C11i | 1.454 (2) |
C6—C7 | 1.381 (3) | N2—C12i | 1.447 (2) |
C6—N1 | 1.405 (2) | C14—O2 | 1.460 (6) |
C7—C8 | 1.376 (3) | C14—C15 | 1.463 (7) |
C7—H7 | 0.9300 | C14—H14A | 0.9700 |
C8—H8 | 0.9300 | C14—H14B | 0.9700 |
C9—N1 | 1.453 (2) | C15—H15A | 0.9600 |
C9—N2 | 1.470 (2) | C15—H15B | 0.9600 |
C9—H9A | 0.9700 | C15—H15C | 0.9600 |
C9—H9B | 0.9700 | C14'—C15' | 1.455 (7) |
C10—O1 | 1.2118 (19) | C14'—O2' | 1.456 (6) |
C10—N3 | 1.363 (2) | C14'—H14C | 0.9700 |
C10—N2 | 1.399 (2) | C14'—H14D | 0.9700 |
C11—N1i | 1.454 (2) | C15'—H15D | 0.9600 |
C11—N3 | 1.458 (2) | C15'—H15E | 0.9600 |
C11—H11A | 0.9700 | C15'—H15F | 0.9600 |
C11—H11B | 0.9700 | ||
C2—C1—H1 | 180.0 | N3—C12—C12i | 101.66 (14) |
C1—C2—C3 | 177.6 (3) | C13—C12—C12i | 115.55 (12) |
C8—C3—C4 | 117.63 (19) | O3—C13—O2 | 127.8 (4) |
C8—C3—C2 | 121.48 (18) | O3'—C13—O2 | 113.3 (5) |
C4—C3—C2 | 120.86 (17) | O3—C13—O2' | 124.3 (5) |
C5—C4—C3 | 120.80 (18) | O3'—C13—O2' | 124.5 (5) |
C5—C4—H4 | 119.6 | O3—C13—C12 | 119.3 (3) |
C3—C4—H4 | 119.6 | O3'—C13—C12 | 127.3 (4) |
C4—C5—C6 | 121.58 (18) | O2—C13—C12 | 112.9 (3) |
C4—C5—H5 | 119.2 | O2'—C13—C12 | 108.2 (3) |
C6—C5—H5 | 119.2 | C6—N1—C9 | 120.04 (15) |
C7—C6—C5 | 117.35 (18) | C6—N1—C11i | 121.63 (16) |
C7—C6—N1 | 123.15 (16) | C9—N1—C11i | 111.16 (15) |
C5—C6—N1 | 119.38 (17) | C10—N2—C12i | 108.53 (14) |
C8—C7—C6 | 120.95 (17) | C10—N2—C9 | 117.71 (15) |
C8—C7—H7 | 119.5 | C12i—N2—C9 | 114.26 (14) |
C6—C7—H7 | 119.5 | C10—N3—C12 | 112.96 (14) |
C7—C8—C3 | 121.65 (19) | C10—N3—C11 | 126.10 (15) |
C7—C8—H8 | 119.2 | C12—N3—C11 | 116.78 (15) |
C3—C8—H8 | 119.2 | O2—C14—C15 | 109.0 (6) |
N1—C9—N2 | 112.24 (14) | O2—C14—H14A | 109.9 |
N1—C9—H9A | 109.2 | C15—C14—H14A | 109.9 |
N2—C9—H9A | 109.2 | O2—C14—H14B | 109.9 |
N1—C9—H9B | 109.2 | C15—C14—H14B | 109.9 |
N2—C9—H9B | 109.2 | H14A—C14—H14B | 108.3 |
H9A—C9—H9B | 107.9 | C13—O2—C14 | 119.1 (5) |
O1—C10—N3 | 126.66 (17) | C15'—C14'—O2' | 110.8 (6) |
O1—C10—N2 | 125.56 (17) | C15'—C14'—H14C | 109.5 |
N3—C10—N2 | 107.74 (14) | O2'—C14'—H14C | 109.5 |
N1i—C11—N3 | 111.55 (14) | C15'—C14'—H14D | 109.5 |
N1i—C11—H11A | 109.3 | O2'—C14'—H14D | 109.5 |
N3—C11—H11A | 109.3 | H14C—C14'—H14D | 108.1 |
N1i—C11—H11B | 109.3 | C14'—C15'—H15D | 109.5 |
N3—C11—H11B | 109.3 | C14'—C15'—H15E | 109.5 |
H11A—C11—H11B | 108.0 | H15D—C15'—H15E | 109.5 |
N2i—C12—N3 | 111.53 (13) | C14'—C15'—H15F | 109.5 |
N2i—C12—C13 | 111.95 (14) | H15D—C15'—H15F | 109.5 |
N3—C12—C13 | 111.03 (14) | H15E—C15'—H15F | 109.5 |
N2i—C12—C12i | 104.58 (15) | C13—O2'—C14' | 122.2 (5) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3ii | 0.93 | 2.35 | 3.226 (7) | 158 |
Symmetry code: (ii) −x, y+1, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C30H28N6O6 |
Mr | 568.58 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 294 |
a, b, c (Å) | 16.0226 (10), 14.0617 (9), 13.7870 (9) |
β (°) | 115.523 (1) |
V (Å3) | 2803.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.20 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12898, 3057, 1952 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.147, 1.05 |
No. of reflections | 3057 |
No. of parameters | 229 |
No. of restraints | 11 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3i | 0.93 | 2.35 | 3.226 (7) | 157.5 |
Symmetry code: (i) −x, y+1, −z+1/2. |
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Glycoluryl derivatives have been employed in many applications, including polymer cross-linking, explosives, stabilization of organic compounds against photo-degradation, textile waste, stream purfication, and comblinational chemistry (Witt et al., 2000). They are also used as building blocks for self assembly, molecular recognition, and catalysis (Rebek, 2005; Rowan et al., 1999). In this paper we report the crystal structure of the title glycoluryl derivative, (I)(Fig. 1), in which the dihedral angle between the imidazolone rings of the glycouril unit is 73.12 (3) ° and the dihedral angle between two phenyl ring is 16.82 (4)°. The molecule lies on a crystallographic twofold axis. In the crystal structure, molecules are connected by wek intermolecular C—H···O hydrogen bonds (Fig. 2).