Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029467/wn2157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029467/wn2157Isup2.hkl |
CCDC reference: 657750
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.007 Å
- R factor = 0.044
- wR factor = 0.079
- Data-to-parameter ratio = 6.3
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.103 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.32 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 300 Ang. PLAT230_ALERT_2_C Hirshfeld Test Diff for N8 - C24 .. 5.85 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 3192 Count of symmetry unique reflns 3196 Completeness (_total/calc) 99.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Sijbesma et al. (1993).
For related literature, see: Hof et al. (2002); van Nunen & Nolte (1997); Rowan et al. (1999); Spek (2003); Wu et al. (2002).
The title compound was synthesized according to a reported procedure (Sijbesma et al., 1993). Crystals appropriate for X-ray data collection were obtained by slow evaporation of a dichloromethane solution at 293 K.
The value of Rint is rather high, due to the poor quality of the crystal. All H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged.
The glycoluril skeleton has served as an important building block for the preparation of a wide variety of supramolecular assemblies (Wu et al., 2002; Hof et al., 2002). A molecular clip is a molecule with a rigid U-shaped cavity in which small aromatic guest molecules can be complexed by hydrogen bonding and aromatic stacking interactions (Rowan et al., 1999). We report here the structure of the title glycoluril derivative (Fig. 1), which is an important intermediate for the preparation of molecular clips (Sijbesma et al., 1993).
In the title glycoluril derivative, C20H18N4O4, the oxadiazinane six-membered ring displays a normal chair conformation. The crystal packing is stabilized by inversion-related intermolecular C—H···O hydrogen bonds, forming dimers (Table 1 and Fig. 2).
For related structures, see: Sijbesma et al. (1993).
For related literature, see: Hof et al. (2002); van Nunen & Nolte (1997); Rowan et al. (1999); Spek (2003); Wu et al. (2002).
Data collection: SMART (Bruker, 2001); cell refinement: 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: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
C20H18N4O4 | F(000) = 1584 |
Mr = 378.39 | Dx = 1.390 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 1636 reflections |
a = 14.558 (3) Å | θ = 2.3–19.1° |
b = 14.870 (3) Å | µ = 0.10 mm−1 |
c = 16.711 (3) Å | T = 292 K |
β = 91.695 (3)° | Block, colorless |
V = 3616.2 (11) Å3 | 0.34 × 0.18 × 0.10 mm |
Z = 8 |
Bruker SMART APEX CCD area-detector diffractometer | 1976 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.103 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
φ and ω scans | h = −17→17 |
13181 measured reflections | k = −17→17 |
3192 independent reflections | l = −19→19 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.80 | w = 1/[σ2(Fo2) + (0.0298P)2] where P = (Fo2 + 2Fc2)/3 |
3192 reflections | (Δ/σ)max = 0.031 |
505 parameters | Δρmax = 0.21 e Å−3 |
2 restraints | Δρmin = −0.19 e Å−3 |
C20H18N4O4 | V = 3616.2 (11) Å3 |
Mr = 378.39 | Z = 8 |
Monoclinic, Cc | Mo Kα radiation |
a = 14.558 (3) Å | µ = 0.10 mm−1 |
b = 14.870 (3) Å | T = 292 K |
c = 16.711 (3) Å | 0.34 × 0.18 × 0.10 mm |
β = 91.695 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 1976 reflections with I > 2σ(I) |
13181 measured reflections | Rint = 0.103 |
3192 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 2 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.80 | Δρmax = 0.21 e Å−3 |
3192 reflections | Δρmin = −0.19 e Å−3 |
505 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 | ||
O2 | 0.2736 (2) | 0.0000 (2) | 1.07844 (17) | 0.0625 (8) | |
N3 | 0.2004 (2) | −0.0824 (2) | 0.9737 (2) | 0.0427 (9) | |
O6 | 0.1405 (3) | 0.2727 (2) | 0.8421 (2) | 0.0719 (11) | |
O4 | 0.32209 (19) | −0.1725 (2) | 0.93918 (18) | 0.0586 (8) | |
N7 | 0.1933 (2) | 0.3802 (2) | 0.6171 (2) | 0.0495 (10) | |
C32 | 0.1428 (3) | 0.5164 (3) | 0.7808 (3) | 0.0504 (12) | |
O3 | 0.3242 (2) | 0.1647 (2) | 0.92934 (18) | 0.0636 (9) | |
O5 | 0.0984 (3) | 0.2795 (2) | 0.5416 (2) | 0.0706 (11) | |
N2 | 0.2398 (2) | 0.0739 (2) | 0.8416 (2) | 0.0441 (9) | |
O8 | −0.0516 (2) | 0.2753 (2) | 0.7105 (2) | 0.0715 (10) | |
N5 | 0.0513 (3) | 0.3769 (2) | 0.7679 (2) | 0.0484 (10) | |
C4 | 0.2627 (3) | 0.1102 (3) | 0.9151 (3) | 0.0487 (13) | |
O7 | 0.2886 (2) | 0.2680 (2) | 0.6714 (2) | 0.0766 (11) | |
N1 | 0.2409 (2) | −0.0855 (2) | 0.8472 (2) | 0.0446 (9) | |
O1 | 0.3609 (2) | −0.0085 (2) | 0.7869 (2) | 0.0699 (9) | |
C33 | 0.1031 (3) | 0.5211 (3) | 0.6098 (3) | 0.0490 (12) | |
N6 | 0.2125 (3) | 0.3696 (2) | 0.7499 (2) | 0.0545 (11) | |
N8 | 0.0315 (3) | 0.3751 (3) | 0.6344 (2) | 0.0524 (10) | |
C3 | 0.2633 (3) | −0.1176 (3) | 0.9227 (3) | 0.0418 (11) | |
C8 | 0.0670 (3) | 0.0662 (3) | 0.7534 (3) | 0.0537 (12) | |
H8 | 0.0897 | 0.1222 | 0.7688 | 0.064* | |
C13 | 0.0529 (3) | −0.0009 (3) | 0.9528 (2) | 0.0430 (10) | |
C10 | −0.0391 (3) | −0.0217 (3) | 0.6751 (3) | 0.0663 (14) | |
H10 | −0.0875 | −0.0252 | 0.6376 | 0.080* | |
N4 | 0.2018 (3) | 0.0780 (2) | 0.9695 (2) | 0.0469 (9) | |
C19 | 0.2208 (3) | −0.0780 (3) | 1.0588 (3) | 0.0578 (12) | |
H19A | 0.1638 | −0.0767 | 1.0875 | 0.069* | |
H19B | 0.2546 | −0.1314 | 1.0755 | 0.069* | |
C26 | 0.1139 (3) | 0.4291 (3) | 0.6466 (3) | 0.0466 (11) | |
C6 | 0.1544 (2) | −0.0026 (3) | 0.9399 (2) | 0.0396 (10) | |
C5 | 0.1822 (3) | −0.0061 (3) | 0.8491 (2) | 0.0412 (10) | |
C25 | 0.1305 (3) | 0.4265 (3) | 0.7406 (3) | 0.0454 (11) | |
C24 | 0.0053 (3) | 0.3347 (3) | 0.7041 (3) | 0.0553 (13) | |
C2 | 0.3063 (3) | 0.0694 (3) | 0.7790 (3) | 0.0590 (13) | |
H2A | 0.2743 | 0.0690 | 0.7272 | 0.071* | |
H2B | 0.3453 | 0.1222 | 0.7816 | 0.071* | |
C20 | 0.2239 (3) | 0.0786 (3) | 1.0545 (3) | 0.0604 (13) | |
H20A | 0.2603 | 0.1315 | 1.0676 | 0.072* | |
H20B | 0.1675 | 0.0820 | 1.0839 | 0.072* | |
C38 | 0.0201 (4) | 0.3307 (4) | 0.5589 (3) | 0.0704 (16) | |
H38A | −0.0333 | 0.2917 | 0.5599 | 0.085* | |
H38B | 0.0095 | 0.3751 | 0.5171 | 0.085* | |
C29 | 0.1627 (6) | 0.6892 (4) | 0.8406 (4) | 0.091 (2) | |
H29 | 0.1692 | 0.7475 | 0.8601 | 0.110* | |
C37 | 0.1791 (4) | 0.5719 (3) | 0.5911 (3) | 0.0608 (14) | |
H37 | 0.2373 | 0.5468 | 0.5974 | 0.073* | |
C18 | 0.0031 (4) | −0.0798 (4) | 0.9634 (3) | 0.0595 (14) | |
H18 | 0.0339 | −0.1344 | 0.9682 | 0.071* | |
C40 | 0.0780 (5) | 0.6480 (4) | 0.8394 (3) | 0.0802 (19) | |
H40 | 0.0272 | 0.6783 | 0.8584 | 0.096* | |
C23 | 0.2359 (3) | 0.3305 (3) | 0.6789 (3) | 0.0552 (13) | |
C7 | 0.1050 (3) | −0.0101 (3) | 0.7867 (2) | 0.0416 (10) | |
C15 | −0.0884 (4) | 0.0822 (4) | 0.9530 (3) | 0.0724 (15) | |
H15 | −0.1195 | 0.1368 | 0.9492 | 0.087* | |
C27 | 0.0685 (4) | 0.5614 (3) | 0.8097 (3) | 0.0639 (14) | |
H27 | 0.0112 | 0.5336 | 0.8094 | 0.077* | |
C1 | 0.3063 (3) | −0.0867 (3) | 0.7844 (3) | 0.0591 (13) | |
H1A | 0.3454 | −0.1393 | 0.7904 | 0.071* | |
H1B | 0.2740 | −0.0907 | 0.7329 | 0.071* | |
C31 | 0.2287 (4) | 0.5576 (4) | 0.7824 (3) | 0.0664 (15) | |
H31 | 0.2797 | 0.5279 | 0.7631 | 0.080* | |
C21 | 0.2212 (4) | 0.3231 (3) | 0.8259 (3) | 0.0664 (16) | |
H21A | 0.2736 | 0.2828 | 0.8251 | 0.080* | |
H21B | 0.2322 | 0.3666 | 0.8684 | 0.080* | |
C12 | 0.0692 (3) | −0.0920 (3) | 0.7631 (3) | 0.0626 (13) | |
H12 | 0.0939 | −0.1445 | 0.7851 | 0.075* | |
C30 | 0.2368 (5) | 0.6445 (4) | 0.8135 (4) | 0.089 (2) | |
H30 | 0.2941 | 0.6722 | 0.8157 | 0.107* | |
C14 | 0.0050 (3) | 0.0797 (4) | 0.9487 (3) | 0.0546 (13) | |
H14 | 0.0372 | 0.1332 | 0.9429 | 0.066* | |
C11 | −0.0027 (3) | −0.0980 (3) | 0.7074 (3) | 0.0723 (15) | |
H11 | −0.0261 | −0.1538 | 0.6923 | 0.087* | |
C17 | −0.0901 (4) | −0.0775 (4) | 0.9669 (3) | 0.0722 (15) | |
H17 | −0.1229 | −0.1307 | 0.9721 | 0.087* | |
C34 | 0.0177 (4) | 0.5610 (4) | 0.6019 (3) | 0.0717 (16) | |
H34 | −0.0347 | 0.5286 | 0.6143 | 0.086* | |
C39 | 0.1772 (4) | 0.3359 (4) | 0.5424 (3) | 0.0643 (15) | |
H39A | 0.1695 | 0.3808 | 0.5006 | 0.077* | |
H39B | 0.2306 | 0.3000 | 0.5303 | 0.077* | |
C22 | 0.0637 (4) | 0.3313 (4) | 0.8440 (3) | 0.0701 (16) | |
H22A | 0.0732 | 0.3753 | 0.8863 | 0.084* | |
H22B | 0.0089 | 0.2971 | 0.8554 | 0.084* | |
C35 | 0.0098 (5) | 0.6486 (4) | 0.5756 (4) | 0.088 (2) | |
H35 | −0.0477 | 0.6756 | 0.5704 | 0.106* | |
C9 | −0.0044 (3) | 0.0610 (3) | 0.6977 (3) | 0.0631 (13) | |
H9 | −0.0292 | 0.1132 | 0.6753 | 0.076* | |
C16 | −0.1361 (4) | 0.0036 (5) | 0.9628 (3) | 0.0780 (17) | |
H16 | −0.1996 | 0.0050 | 0.9668 | 0.094* | |
C41 | 0.0865 (6) | 0.6952 (4) | 0.5574 (4) | 0.092 (2) | |
H41 | 0.0807 | 0.7545 | 0.5403 | 0.111* | |
C36 | 0.1708 (5) | 0.6584 (4) | 0.5633 (3) | 0.0835 (19) | |
H36 | 0.2224 | 0.6909 | 0.5489 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.071 (2) | 0.065 (2) | 0.0495 (19) | 0.0027 (19) | −0.0192 (15) | 0.0024 (17) |
N3 | 0.045 (2) | 0.041 (2) | 0.042 (2) | 0.0059 (18) | −0.0019 (18) | 0.0072 (17) |
O6 | 0.082 (3) | 0.052 (2) | 0.081 (3) | 0.000 (2) | −0.004 (2) | 0.0136 (18) |
O4 | 0.0484 (18) | 0.0577 (19) | 0.069 (2) | 0.0152 (16) | −0.0124 (16) | 0.0025 (16) |
N7 | 0.046 (2) | 0.045 (2) | 0.058 (3) | 0.001 (2) | 0.002 (2) | −0.008 (2) |
C32 | 0.063 (3) | 0.037 (3) | 0.051 (3) | −0.007 (3) | −0.013 (2) | 0.001 (2) |
O3 | 0.063 (2) | 0.059 (2) | 0.067 (2) | −0.0252 (18) | −0.0222 (17) | 0.0044 (16) |
O5 | 0.081 (3) | 0.058 (2) | 0.073 (3) | −0.011 (2) | 0.003 (2) | −0.0200 (18) |
N2 | 0.045 (2) | 0.045 (2) | 0.042 (2) | −0.0077 (18) | −0.0079 (18) | 0.0072 (17) |
O8 | 0.058 (2) | 0.054 (2) | 0.104 (3) | −0.016 (2) | 0.0178 (19) | −0.021 (2) |
N5 | 0.058 (3) | 0.036 (2) | 0.052 (2) | −0.008 (2) | 0.002 (2) | −0.0065 (19) |
C4 | 0.052 (3) | 0.036 (3) | 0.057 (3) | 0.001 (2) | −0.020 (3) | 0.009 (2) |
O7 | 0.065 (2) | 0.052 (2) | 0.112 (3) | 0.0186 (19) | −0.007 (2) | −0.010 (2) |
N1 | 0.046 (2) | 0.044 (2) | 0.044 (2) | 0.0087 (17) | −0.0023 (18) | −0.0031 (18) |
O1 | 0.0510 (19) | 0.081 (3) | 0.078 (2) | −0.0008 (19) | 0.0118 (16) | 0.008 (2) |
C33 | 0.059 (3) | 0.042 (3) | 0.045 (3) | 0.003 (3) | −0.010 (2) | −0.001 (2) |
N6 | 0.049 (2) | 0.048 (2) | 0.066 (3) | 0.006 (2) | −0.014 (2) | 0.001 (2) |
N8 | 0.049 (2) | 0.053 (2) | 0.055 (3) | −0.014 (2) | −0.004 (2) | −0.010 (2) |
C3 | 0.040 (3) | 0.037 (3) | 0.047 (3) | −0.001 (2) | −0.015 (2) | 0.001 (2) |
C8 | 0.059 (3) | 0.056 (3) | 0.045 (3) | 0.009 (2) | −0.011 (2) | −0.008 (2) |
C13 | 0.042 (2) | 0.051 (3) | 0.036 (2) | 0.000 (3) | −0.0019 (18) | 0.003 (2) |
C10 | 0.061 (3) | 0.080 (4) | 0.056 (3) | 0.006 (3) | −0.027 (3) | −0.007 (3) |
N4 | 0.056 (2) | 0.043 (2) | 0.041 (2) | −0.0051 (19) | −0.0121 (19) | 0.0018 (18) |
C19 | 0.069 (3) | 0.055 (3) | 0.049 (3) | 0.000 (3) | −0.007 (3) | 0.009 (2) |
C26 | 0.044 (3) | 0.042 (3) | 0.054 (3) | −0.001 (2) | −0.007 (2) | −0.003 (2) |
C6 | 0.042 (2) | 0.037 (2) | 0.039 (2) | 0.000 (3) | −0.007 (2) | 0.002 (2) |
C5 | 0.043 (2) | 0.041 (2) | 0.040 (2) | 0.000 (2) | −0.0047 (19) | 0.000 (2) |
C25 | 0.046 (3) | 0.038 (3) | 0.052 (3) | −0.002 (2) | −0.005 (2) | −0.002 (2) |
C24 | 0.042 (3) | 0.039 (3) | 0.085 (4) | 0.002 (3) | 0.004 (3) | −0.017 (3) |
C2 | 0.054 (3) | 0.059 (3) | 0.064 (3) | −0.005 (3) | 0.003 (3) | 0.012 (3) |
C20 | 0.077 (3) | 0.055 (3) | 0.048 (3) | −0.004 (3) | −0.016 (3) | −0.009 (2) |
C38 | 0.066 (4) | 0.074 (4) | 0.071 (4) | −0.012 (3) | −0.005 (3) | −0.028 (3) |
C29 | 0.130 (6) | 0.038 (3) | 0.102 (5) | −0.006 (4) | −0.066 (5) | −0.003 (3) |
C37 | 0.065 (4) | 0.048 (3) | 0.070 (4) | 0.001 (3) | 0.002 (3) | 0.007 (3) |
C18 | 0.053 (3) | 0.065 (4) | 0.060 (4) | −0.005 (3) | −0.005 (3) | 0.008 (3) |
C40 | 0.111 (5) | 0.048 (3) | 0.080 (4) | 0.012 (3) | −0.026 (4) | −0.014 (3) |
C23 | 0.047 (3) | 0.048 (3) | 0.070 (4) | −0.003 (3) | −0.005 (3) | −0.006 (3) |
C7 | 0.046 (2) | 0.046 (3) | 0.033 (2) | 0.000 (2) | −0.0050 (18) | 0.000 (2) |
C15 | 0.059 (4) | 0.096 (5) | 0.061 (3) | 0.023 (3) | −0.009 (3) | 0.004 (3) |
C27 | 0.078 (4) | 0.047 (3) | 0.066 (3) | 0.005 (3) | −0.014 (3) | −0.010 (3) |
C1 | 0.058 (3) | 0.067 (3) | 0.052 (3) | 0.009 (3) | −0.001 (3) | −0.002 (3) |
C31 | 0.067 (4) | 0.064 (3) | 0.067 (4) | −0.015 (3) | −0.017 (3) | 0.008 (3) |
C21 | 0.072 (4) | 0.053 (3) | 0.072 (4) | 0.012 (3) | −0.022 (3) | 0.001 (3) |
C12 | 0.061 (3) | 0.053 (3) | 0.072 (3) | −0.006 (2) | −0.024 (3) | 0.007 (3) |
C30 | 0.111 (6) | 0.051 (4) | 0.101 (5) | −0.030 (4) | −0.060 (5) | 0.016 (3) |
C14 | 0.049 (3) | 0.067 (4) | 0.047 (3) | 0.012 (3) | −0.004 (2) | −0.005 (2) |
C11 | 0.080 (4) | 0.059 (3) | 0.076 (4) | −0.008 (3) | −0.024 (3) | −0.009 (3) |
C17 | 0.052 (3) | 0.094 (4) | 0.070 (4) | −0.017 (3) | −0.006 (3) | 0.009 (3) |
C34 | 0.069 (4) | 0.060 (4) | 0.085 (4) | 0.005 (3) | −0.028 (3) | 0.006 (3) |
C39 | 0.065 (4) | 0.059 (3) | 0.069 (4) | 0.000 (3) | 0.009 (3) | −0.006 (3) |
C22 | 0.091 (4) | 0.059 (4) | 0.061 (4) | −0.003 (3) | 0.006 (3) | 0.013 (3) |
C35 | 0.087 (5) | 0.070 (4) | 0.105 (5) | 0.026 (4) | −0.034 (4) | −0.004 (4) |
C9 | 0.073 (3) | 0.061 (3) | 0.054 (3) | 0.007 (3) | −0.017 (3) | −0.001 (3) |
C16 | 0.044 (3) | 0.124 (5) | 0.065 (4) | 0.013 (4) | −0.001 (2) | 0.007 (4) |
C41 | 0.133 (7) | 0.056 (4) | 0.086 (5) | 0.018 (5) | −0.023 (5) | 0.016 (3) |
C36 | 0.103 (5) | 0.061 (4) | 0.088 (5) | −0.002 (4) | 0.005 (4) | 0.007 (3) |
O2—C20 | 1.426 (5) | C19—H19A | 0.9700 |
O2—C19 | 1.425 (5) | C19—H19B | 0.9700 |
N3—C3 | 1.374 (5) | C26—C25 | 1.583 (5) |
N3—C19 | 1.446 (5) | C6—C5 | 1.583 (5) |
N3—C6 | 1.467 (5) | C5—C7 | 1.512 (5) |
O6—C22 | 1.418 (6) | C2—H2A | 0.9700 |
O6—C21 | 1.426 (6) | C2—H2B | 0.9700 |
O4—C3 | 1.209 (4) | C20—H20A | 0.9700 |
N7—C23 | 1.399 (6) | C20—H20B | 0.9700 |
N7—C39 | 1.426 (6) | C38—H38A | 0.9700 |
N7—C26 | 1.463 (6) | C38—H38B | 0.9700 |
C32—C27 | 1.373 (7) | C29—C30 | 1.356 (8) |
C32—C31 | 1.393 (7) | C29—C40 | 1.377 (9) |
C32—C25 | 1.504 (6) | C29—H29 | 0.9300 |
O3—C4 | 1.226 (5) | C37—C36 | 1.371 (7) |
O5—C38 | 1.409 (6) | C37—H37 | 0.9300 |
O5—C39 | 1.420 (6) | C18—C17 | 1.361 (7) |
N2—C4 | 1.373 (5) | C18—H18 | 0.9300 |
N2—C2 | 1.448 (5) | C40—C27 | 1.385 (7) |
N2—C5 | 1.463 (5) | C40—H40 | 0.9300 |
O8—C24 | 1.217 (5) | C7—C12 | 1.379 (5) |
N5—C24 | 1.391 (5) | C15—C14 | 1.364 (7) |
N5—C22 | 1.447 (6) | C15—C16 | 1.372 (7) |
N5—C25 | 1.454 (6) | C15—H15 | 0.9300 |
C4—N4 | 1.374 (6) | C27—H27 | 0.9300 |
O7—C23 | 1.214 (5) | C1—H1A | 0.9700 |
N1—C3 | 1.378 (5) | C1—H1B | 0.9700 |
N1—C1 | 1.439 (5) | C31—C30 | 1.396 (7) |
N1—C5 | 1.458 (5) | C31—H31 | 0.9300 |
O1—C2 | 1.409 (5) | C21—H21A | 0.9700 |
O1—C1 | 1.408 (5) | C21—H21B | 0.9700 |
C33—C34 | 1.380 (6) | C12—C11 | 1.383 (5) |
C33—C37 | 1.383 (6) | C12—H12 | 0.9300 |
C33—C26 | 1.507 (6) | C30—H30 | 0.9300 |
N6—C23 | 1.373 (6) | C14—H14 | 0.9300 |
N6—C21 | 1.449 (6) | C11—H11 | 0.9300 |
N6—C25 | 1.467 (5) | C17—C16 | 1.381 (7) |
N8—C24 | 1.375 (6) | C17—H17 | 0.9300 |
N8—C38 | 1.430 (6) | C34—C35 | 1.379 (8) |
N8—C26 | 1.452 (5) | C34—H34 | 0.9300 |
C8—C9 | 1.377 (5) | C39—H39A | 0.9700 |
C8—C7 | 1.372 (5) | C39—H39B | 0.9700 |
C8—H8 | 0.9300 | C22—H22A | 0.9700 |
C13—C14 | 1.387 (6) | C22—H22B | 0.9700 |
C13—C18 | 1.393 (6) | C35—C41 | 1.357 (8) |
C13—C6 | 1.500 (6) | C35—H35 | 0.9300 |
C10—C11 | 1.357 (6) | C9—H9 | 0.9300 |
C10—C9 | 1.377 (6) | C16—H16 | 0.9300 |
C10—H10 | 0.9300 | C41—C36 | 1.345 (8) |
N4—C20 | 1.447 (5) | C41—H41 | 0.9300 |
N4—C6 | 1.462 (5) | C36—H36 | 0.9300 |
C20—O2—C19 | 109.7 (3) | N4—C20—H20B | 109.3 |
C3—N3—C19 | 120.5 (3) | H20A—C20—H20B | 108.0 |
C3—N3—C6 | 112.0 (3) | O5—C38—N8 | 110.9 (4) |
C19—N3—C6 | 114.9 (3) | O5—C38—H38A | 109.5 |
C22—O6—C21 | 109.6 (4) | N8—C38—H38A | 109.5 |
C23—N7—C39 | 117.4 (4) | O5—C38—H38B | 109.5 |
C23—N7—C26 | 110.6 (4) | N8—C38—H38B | 109.5 |
C39—N7—C26 | 114.4 (4) | H38A—C38—H38B | 108.0 |
C27—C32—C31 | 119.7 (5) | C30—C29—C40 | 119.9 (6) |
C27—C32—C25 | 120.4 (4) | C30—C29—H29 | 120.1 |
C31—C32—C25 | 119.6 (5) | C40—C29—H29 | 120.1 |
C38—O5—C39 | 109.7 (4) | C36—C37—C33 | 121.7 (5) |
C4—N2—C2 | 121.0 (4) | C36—C37—H37 | 119.1 |
C4—N2—C5 | 111.6 (3) | C33—C37—H37 | 119.1 |
C2—N2—C5 | 114.9 (3) | C17—C18—C13 | 120.5 (5) |
C24—N5—C22 | 120.5 (4) | C17—C18—H18 | 119.7 |
C24—N5—C25 | 110.9 (4) | C13—C18—H18 | 119.7 |
C22—N5—C25 | 115.6 (4) | C29—C40—C27 | 119.9 (6) |
O3—C4—N2 | 126.1 (5) | C29—C40—H40 | 120.0 |
O3—C4—N4 | 125.7 (4) | C27—C40—H40 | 120.0 |
N2—C4—N4 | 108.1 (4) | O7—C23—N6 | 126.0 (5) |
C3—N1—C1 | 121.3 (3) | O7—C23—N7 | 126.5 (5) |
C3—N1—C5 | 112.6 (3) | N6—C23—N7 | 107.3 (4) |
C1—N1—C5 | 115.3 (3) | C8—C7—C12 | 118.0 (4) |
C2—O1—C1 | 111.1 (3) | C8—C7—C5 | 122.0 (4) |
C34—C33—C37 | 117.9 (4) | C12—C7—C5 | 120.0 (4) |
C34—C33—C26 | 120.8 (5) | C14—C15—C16 | 119.4 (5) |
C37—C33—C26 | 120.9 (4) | C14—C15—H15 | 120.3 |
C23—N6—C21 | 122.6 (4) | C16—C15—H15 | 120.3 |
C23—N6—C25 | 112.0 (4) | C32—C27—C40 | 120.5 (6) |
C21—N6—C25 | 114.7 (4) | C32—C27—H27 | 119.7 |
C24—N8—C38 | 121.2 (4) | C40—C27—H27 | 119.7 |
C24—N8—C26 | 111.8 (4) | O1—C1—N1 | 110.6 (4) |
C38—N8—C26 | 116.9 (4) | O1—C1—H1A | 109.5 |
O4—C3—N3 | 126.6 (4) | N1—C1—H1A | 109.5 |
O4—C3—N1 | 126.2 (4) | O1—C1—H1B | 109.5 |
N3—C3—N1 | 107.0 (3) | N1—C1—H1B | 109.5 |
C9—C8—C7 | 121.0 (4) | H1A—C1—H1B | 108.1 |
C9—C8—H8 | 119.5 | C32—C31—C30 | 118.7 (6) |
C7—C8—H8 | 119.5 | C32—C31—H31 | 120.7 |
C14—C13—C18 | 118.1 (4) | C30—C31—H31 | 120.6 |
C14—C13—C6 | 120.3 (4) | O6—C21—N6 | 111.4 (4) |
C18—C13—C6 | 121.5 (4) | O6—C21—H21A | 109.4 |
C11—C10—C9 | 120.1 (4) | N6—C21—H21A | 109.3 |
C11—C10—H10 | 119.9 | O6—C21—H21B | 109.4 |
C9—C10—H10 | 119.9 | N6—C21—H21B | 109.4 |
C4—N4—C20 | 121.2 (4) | H21A—C21—H21B | 108.0 |
C4—N4—C6 | 111.6 (3) | C11—C12—C7 | 121.4 (4) |
C20—N4—C6 | 115.2 (3) | C11—C12—H12 | 119.3 |
O2—C19—N3 | 110.9 (3) | C7—C12—H12 | 119.3 |
O2—C19—H19A | 109.5 | C29—C30—C31 | 121.3 (6) |
N3—C19—H19A | 109.5 | C29—C30—H30 | 119.4 |
O2—C19—H19B | 109.5 | C31—C30—H30 | 119.4 |
N3—C19—H19B | 109.5 | C15—C14—C13 | 121.5 (5) |
H19A—C19—H19B | 108.0 | C15—C14—H14 | 119.3 |
N8—C26—N7 | 109.6 (3) | C13—C14—H14 | 119.3 |
N8—C26—C33 | 111.6 (4) | C10—C11—C12 | 119.6 (4) |
N7—C26—C33 | 112.8 (4) | C10—C11—H11 | 120.2 |
N8—C26—C25 | 103.1 (4) | C12—C11—H11 | 120.2 |
N7—C26—C25 | 102.9 (3) | C18—C17—C16 | 120.2 (5) |
C33—C26—C25 | 116.0 (4) | C18—C17—H17 | 119.9 |
N4—C6—N3 | 109.1 (3) | C16—C17—H17 | 119.9 |
N4—C6—C13 | 113.2 (3) | C35—C34—C33 | 120.2 (6) |
N3—C6—C13 | 113.5 (3) | C35—C34—H34 | 119.9 |
N4—C6—C5 | 102.7 (3) | C33—C34—H34 | 119.9 |
N3—C6—C5 | 102.5 (3) | O5—C39—N7 | 113.1 (4) |
C13—C6—C5 | 114.8 (3) | O5—C39—H39A | 108.9 |
N1—C5—N2 | 108.6 (3) | N7—C39—H39A | 108.9 |
N1—C5—C7 | 112.2 (3) | O5—C39—H39B | 109.0 |
N2—C5—C7 | 112.9 (3) | N7—C39—H39B | 109.0 |
N1—C5—C6 | 102.3 (3) | H39A—C39—H39B | 107.8 |
N2—C5—C6 | 102.6 (3) | O6—C22—N5 | 110.3 (4) |
C7—C5—C6 | 117.2 (3) | O6—C22—H22A | 109.6 |
N5—C25—N6 | 109.0 (3) | N5—C22—H22A | 109.6 |
N5—C25—C32 | 113.3 (4) | O6—C22—H22B | 109.6 |
N6—C25—C32 | 112.3 (4) | N5—C22—H22B | 109.6 |
N5—C25—C26 | 103.0 (3) | H22A—C22—H22B | 108.1 |
N6—C25—C26 | 102.6 (3) | C41—C35—C34 | 119.5 (6) |
C32—C25—C26 | 115.7 (4) | C41—C35—H35 | 120.2 |
O8—C24—N8 | 126.7 (5) | C34—C35—H35 | 120.2 |
O8—C24—N5 | 124.9 (5) | C8—C9—C10 | 119.9 (4) |
N8—C24—N5 | 108.2 (4) | C8—C9—H9 | 120.1 |
O1—C2—N2 | 110.9 (4) | C10—C9—H9 | 120.1 |
O1—C2—H2A | 109.5 | C15—C16—C17 | 120.3 (5) |
N2—C2—H2A | 109.5 | C15—C16—H16 | 119.9 |
O1—C2—H2B | 109.5 | C17—C16—H16 | 119.9 |
N2—C2—H2B | 109.5 | C36—C41—C35 | 122.1 (6) |
H2A—C2—H2B | 108.0 | C36—C41—H41 | 119.0 |
O2—C20—N4 | 111.5 (3) | C35—C41—H41 | 119.0 |
O2—C20—H20A | 109.3 | C41—C36—C37 | 118.5 (6) |
N4—C20—H20A | 109.3 | C41—C36—H36 | 120.7 |
O2—C20—H20B | 109.3 | C37—C36—H36 | 120.7 |
C2—N2—C4—O3 | 24.0 (6) | C31—C32—C25—N5 | 158.4 (4) |
C5—N2—C4—O3 | 164.0 (4) | C27—C32—C25—N6 | −151.2 (4) |
C2—N2—C4—N4 | −158.9 (4) | C31—C32—C25—N6 | 34.4 (6) |
C5—N2—C4—N4 | −18.9 (4) | C27—C32—C25—C26 | 91.4 (5) |
C19—N3—C3—O4 | 26.4 (6) | C31—C32—C25—C26 | −83.0 (5) |
C6—N3—C3—O4 | 166.1 (4) | N8—C26—C25—N5 | −4.0 (4) |
C19—N3—C3—N1 | −159.5 (3) | N7—C26—C25—N5 | −118.0 (3) |
C6—N3—C3—N1 | −19.7 (4) | C33—C26—C25—N5 | 118.3 (4) |
C1—N1—C3—O4 | −24.4 (6) | N8—C26—C25—N6 | 109.2 (3) |
C5—N1—C3—O4 | −167.0 (4) | N7—C26—C25—N6 | −4.8 (4) |
C1—N1—C3—N3 | 161.4 (4) | C33—C26—C25—N6 | −128.5 (4) |
C5—N1—C3—N3 | 18.8 (4) | N8—C26—C25—C32 | −128.1 (4) |
O3—C4—N4—C20 | −23.6 (7) | N7—C26—C25—C32 | 117.9 (4) |
N2—C4—N4—C20 | 159.2 (3) | C33—C26—C25—C32 | −5.8 (5) |
O3—C4—N4—C6 | −164.5 (4) | C38—N8—C24—O8 | −23.3 (7) |
N2—C4—N4—C6 | 18.3 (4) | C26—N8—C24—O8 | −167.7 (4) |
C20—O2—C19—N3 | 59.5 (5) | C38—N8—C24—N5 | 160.0 (4) |
C3—N3—C19—O2 | 83.4 (5) | C26—N8—C24—N5 | 15.6 (5) |
C6—N3—C19—O2 | −55.3 (5) | C22—N5—C24—O8 | 25.2 (7) |
C24—N8—C26—N7 | 102.2 (4) | C25—N5—C24—O8 | 164.8 (4) |
C38—N8—C26—N7 | −43.8 (5) | C22—N5—C24—N8 | −158.1 (4) |
C24—N8—C26—C33 | −132.0 (4) | C25—N5—C24—N8 | −18.5 (5) |
C38—N8—C26—C33 | 82.0 (5) | C1—O1—C2—N2 | 58.4 (5) |
C24—N8—C26—C25 | −6.8 (5) | C4—N2—C2—O1 | 85.2 (5) |
C38—N8—C26—C25 | −152.8 (4) | C5—N2—C2—O1 | −53.6 (4) |
C23—N7—C26—N8 | −92.6 (4) | C19—O2—C20—N4 | −58.6 (5) |
C39—N7—C26—N8 | 42.7 (5) | C4—N4—C20—O2 | −86.3 (5) |
C23—N7—C26—C33 | 142.3 (4) | C6—N4—C20—O2 | 53.3 (5) |
C39—N7—C26—C33 | −82.5 (5) | C39—O5—C38—N8 | −57.4 (5) |
C23—N7—C26—C25 | 16.6 (4) | C24—N8—C38—O5 | −90.0 (6) |
C39—N7—C26—C25 | 151.8 (4) | C26—N8—C38—O5 | 52.7 (6) |
C34—C33—C26—N8 | 28.2 (6) | C34—C33—C37—C36 | −1.7 (7) |
C37—C33—C26—N8 | −158.7 (4) | C26—C33—C37—C36 | −174.9 (5) |
C34—C33—C26—N7 | 152.3 (4) | C14—C13—C18—C17 | 2.1 (6) |
C37—C33—C26—N7 | −34.7 (6) | C6—C13—C18—C17 | −173.3 (4) |
C34—C33—C26—C25 | −89.4 (5) | C30—C29—C40—C27 | −0.6 (9) |
C37—C33—C26—C25 | 83.6 (5) | C21—N6—C23—O7 | −22.5 (7) |
C4—N4—C6—N3 | 97.8 (4) | C25—N6—C23—O7 | −165.0 (5) |
C20—N4—C6—N3 | −45.6 (4) | C21—N6—C23—N7 | 161.8 (4) |
C4—N4—C6—C13 | −134.8 (4) | C25—N6—C23—N7 | 19.2 (5) |
C20—N4—C6—C13 | 81.8 (4) | C39—N7—C23—O7 | 27.9 (7) |
C4—N4—C6—C5 | −10.4 (4) | C26—N7—C23—O7 | 161.6 (5) |
C20—N4—C6—C5 | −153.8 (3) | C39—N7—C23—N6 | −156.4 (4) |
C3—N3—C6—N4 | −95.5 (4) | C26—N7—C23—N6 | −22.6 (5) |
C19—N3—C6—N4 | 46.6 (4) | C9—C8—C7—C12 | −0.6 (6) |
C3—N3—C6—C13 | 137.2 (3) | C9—C8—C7—C5 | −178.8 (4) |
C19—N3—C6—C13 | −80.6 (4) | N1—C5—C7—C8 | −151.5 (4) |
C3—N3—C6—C5 | 12.8 (4) | N2—C5—C7—C8 | −28.4 (5) |
C19—N3—C6—C5 | 155.0 (3) | C6—C5—C7—C8 | 90.6 (5) |
C14—C13—C6—N4 | 34.0 (5) | N1—C5—C7—C12 | 30.2 (5) |
C18—C13—C6—N4 | −150.7 (4) | N2—C5—C7—C12 | 153.4 (4) |
C14—C13—C6—N3 | 159.1 (4) | C6—C5—C7—C12 | −87.7 (5) |
C18—C13—C6—N3 | −25.6 (5) | C31—C32—C27—C40 | 1.0 (7) |
C14—C13—C6—C5 | −83.5 (5) | C25—C32—C27—C40 | −173.5 (5) |
C18—C13—C6—C5 | 91.8 (5) | C29—C40—C27—C32 | −0.6 (8) |
C3—N1—C5—N2 | 97.7 (4) | C2—O1—C1—N1 | −58.8 (5) |
C1—N1—C5—N2 | −47.3 (4) | C3—N1—C1—O1 | −87.0 (5) |
C3—N1—C5—C7 | −136.8 (3) | C5—N1—C1—O1 | 54.6 (4) |
C1—N1—C5—C7 | 78.3 (4) | C27—C32—C31—C30 | −0.1 (7) |
C3—N1—C5—C6 | −10.4 (4) | C25—C32—C31—C30 | 174.3 (4) |
C1—N1—C5—C6 | −155.3 (3) | C22—O6—C21—N6 | −59.5 (5) |
C4—N2—C5—N1 | −96.0 (4) | C23—N6—C21—O6 | −88.0 (5) |
C2—N2—C5—N1 | 46.6 (4) | C25—N6—C21—O6 | 53.6 (5) |
C4—N2—C5—C7 | 138.9 (3) | C8—C7—C12—C11 | 0.3 (7) |
C2—N2—C5—C7 | −78.5 (4) | C5—C7—C12—C11 | 178.6 (4) |
C4—N2—C5—C6 | 11.8 (4) | C40—C29—C30—C31 | 1.4 (9) |
C2—N2—C5—C6 | 154.4 (3) | C32—C31—C30—C29 | −1.1 (8) |
N4—C6—C5—N1 | 111.8 (3) | C16—C15—C14—C13 | 1.0 (7) |
N3—C6—C5—N1 | −1.4 (3) | C18—C13—C14—C15 | −1.5 (6) |
C13—C6—C5—N1 | −124.9 (3) | C6—C13—C14—C15 | 174.0 (4) |
N4—C6—C5—N2 | −0.8 (3) | C9—C10—C11—C12 | 0.0 (8) |
N3—C6—C5—N2 | −114.0 (3) | C7—C12—C11—C10 | 0.0 (8) |
C13—C6—C5—N2 | 122.5 (3) | C13—C18—C17—C16 | −2.3 (7) |
N4—C6—C5—C7 | −125.1 (3) | C37—C33—C34—C35 | 0.3 (7) |
N3—C6—C5—C7 | 121.7 (3) | C26—C33—C34—C35 | 173.5 (5) |
C13—C6—C5—C7 | −1.8 (5) | C38—O5—C39—N7 | 58.8 (5) |
C24—N5—C25—N6 | −94.9 (4) | C23—N7—C39—O5 | 79.7 (5) |
C22—N5—C25—N6 | 46.8 (5) | C26—N7—C39—O5 | −52.4 (5) |
C24—N5—C25—C32 | 139.2 (4) | C21—O6—C22—N5 | 59.7 (5) |
C22—N5—C25—C32 | −79.1 (5) | C24—N5—C22—O6 | 82.3 (5) |
C24—N5—C25—C26 | 13.5 (4) | C25—N5—C22—O6 | −55.5 (5) |
C22—N5—C25—C26 | 155.2 (4) | C33—C34—C35—C41 | 0.2 (9) |
C23—N6—C25—N5 | 100.2 (4) | C7—C8—C9—C10 | 0.5 (7) |
C21—N6—C25—N5 | −45.5 (5) | C11—C10—C9—C8 | −0.3 (8) |
C23—N6—C25—C32 | −133.4 (4) | C14—C15—C16—C17 | −1.2 (7) |
C21—N6—C25—C32 | 81.0 (5) | C18—C17—C16—C15 | 1.8 (7) |
C23—N6—C25—C26 | −8.5 (5) | C34—C35—C41—C36 | 0.7 (10) |
C21—N6—C25—C26 | −154.1 (4) | C35—C41—C36—C37 | −2.1 (10) |
C27—C32—C25—N5 | −27.1 (6) | C33—C37—C36—C41 | 2.6 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O8i | 0.97 | 2.40 | 3.188 (5) | 138 |
C27—H27···O1ii | 0.93 | 2.30 | 3.208 (7) | 166 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C20H18N4O4 |
Mr | 378.39 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 292 |
a, b, c (Å) | 14.558 (3), 14.870 (3), 16.711 (3) |
β (°) | 91.695 (3) |
V (Å3) | 3616.2 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.34 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13181, 3192, 1976 |
Rint | 0.103 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.079, 0.80 |
No. of reflections | 3192 |
No. of parameters | 505 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O8i | 0.97 | 2.40 | 3.188 (5) | 138.0 |
C27—H27···O1ii | 0.93 | 2.30 | 3.208 (7) | 166.2 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x−1/2, y+1/2, z. |
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The glycoluril skeleton has served as an important building block for the preparation of a wide variety of supramolecular assemblies (Wu et al., 2002; Hof et al., 2002). A molecular clip is a molecule with a rigid U-shaped cavity in which small aromatic guest molecules can be complexed by hydrogen bonding and aromatic stacking interactions (Rowan et al., 1999). We report here the structure of the title glycoluril derivative (Fig. 1), which is an important intermediate for the preparation of molecular clips (Sijbesma et al., 1993).
In the title glycoluril derivative, C20H18N4O4, the oxadiazinane six-membered ring displays a normal chair conformation. The crystal packing is stabilized by inversion-related intermolecular C—H···O hydrogen bonds, forming dimers (Table 1 and Fig. 2).