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The title compound, C20H18N4O4, is a glycoluril derivative. The oxadiazinane six-membered ring displays a normal chair conformation. Inter­molecular C—H...O hydrogen bonds are present in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029467/wn2157sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029467/wn2157Isup2.hkl
Contains datablock I

CCDC reference: 657750

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram for the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
8 b,8c-Diphenyl-2,6-dioxa-3a,4a,7a,8a-tetraazaperhydrocyclopenta[def]fluorene- 4,8-dione top
Crystal data top
C20H18N4O4F(000) = 1584
Mr = 378.39Dx = 1.390 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1636 reflections
a = 14.558 (3) Åθ = 2.3–19.1°
b = 14.870 (3) ŵ = 0.10 mm1
c = 16.711 (3) ÅT = 292 K
β = 91.695 (3)°Block, colorless
V = 3616.2 (11) Å30.34 × 0.18 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1976 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.103
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
φ and ω scansh = 1717
13181 measured reflectionsk = 1717
3192 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-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 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = 0.19 e Å3
Crystal data top
C20H18N4O4V = 3616.2 (11) Å3
Mr = 378.39Z = 8
Monoclinic, CcMo Kα radiation
a = 14.558 (3) ŵ = 0.10 mm1
b = 14.870 (3) ÅT = 292 K
c = 16.711 (3) Å0.34 × 0.18 × 0.10 mm
β = 91.695 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1976 reflections with I > 2σ(I)
13181 measured reflectionsRint = 0.103
3192 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0442 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 0.80Δρmax = 0.21 e Å3
3192 reflectionsΔρmin = 0.19 e Å3
505 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
xyzUiso*/Ueq
O20.2736 (2)0.0000 (2)1.07844 (17)0.0625 (8)
N30.2004 (2)0.0824 (2)0.9737 (2)0.0427 (9)
O60.1405 (3)0.2727 (2)0.8421 (2)0.0719 (11)
O40.32209 (19)0.1725 (2)0.93918 (18)0.0586 (8)
N70.1933 (2)0.3802 (2)0.6171 (2)0.0495 (10)
C320.1428 (3)0.5164 (3)0.7808 (3)0.0504 (12)
O30.3242 (2)0.1647 (2)0.92934 (18)0.0636 (9)
O50.0984 (3)0.2795 (2)0.5416 (2)0.0706 (11)
N20.2398 (2)0.0739 (2)0.8416 (2)0.0441 (9)
O80.0516 (2)0.2753 (2)0.7105 (2)0.0715 (10)
N50.0513 (3)0.3769 (2)0.7679 (2)0.0484 (10)
C40.2627 (3)0.1102 (3)0.9151 (3)0.0487 (13)
O70.2886 (2)0.2680 (2)0.6714 (2)0.0766 (11)
N10.2409 (2)0.0855 (2)0.8472 (2)0.0446 (9)
O10.3609 (2)0.0085 (2)0.7869 (2)0.0699 (9)
C330.1031 (3)0.5211 (3)0.6098 (3)0.0490 (12)
N60.2125 (3)0.3696 (2)0.7499 (2)0.0545 (11)
N80.0315 (3)0.3751 (3)0.6344 (2)0.0524 (10)
C30.2633 (3)0.1176 (3)0.9227 (3)0.0418 (11)
C80.0670 (3)0.0662 (3)0.7534 (3)0.0537 (12)
H80.08970.12220.76880.064*
C130.0529 (3)0.0009 (3)0.9528 (2)0.0430 (10)
C100.0391 (3)0.0217 (3)0.6751 (3)0.0663 (14)
H100.08750.02520.63760.080*
N40.2018 (3)0.0780 (2)0.9695 (2)0.0469 (9)
C190.2208 (3)0.0780 (3)1.0588 (3)0.0578 (12)
H19A0.16380.07671.08750.069*
H19B0.25460.13141.07550.069*
C260.1139 (3)0.4291 (3)0.6466 (3)0.0466 (11)
C60.1544 (2)0.0026 (3)0.9399 (2)0.0396 (10)
C50.1822 (3)0.0061 (3)0.8491 (2)0.0412 (10)
C250.1305 (3)0.4265 (3)0.7406 (3)0.0454 (11)
C240.0053 (3)0.3347 (3)0.7041 (3)0.0553 (13)
C20.3063 (3)0.0694 (3)0.7790 (3)0.0590 (13)
H2A0.27430.06900.72720.071*
H2B0.34530.12220.78160.071*
C200.2239 (3)0.0786 (3)1.0545 (3)0.0604 (13)
H20A0.26030.13151.06760.072*
H20B0.16750.08201.08390.072*
C380.0201 (4)0.3307 (4)0.5589 (3)0.0704 (16)
H38A0.03330.29170.55990.085*
H38B0.00950.37510.51710.085*
C290.1627 (6)0.6892 (4)0.8406 (4)0.091 (2)
H290.16920.74750.86010.110*
C370.1791 (4)0.5719 (3)0.5911 (3)0.0608 (14)
H370.23730.54680.59740.073*
C180.0031 (4)0.0798 (4)0.9634 (3)0.0595 (14)
H180.03390.13440.96820.071*
C400.0780 (5)0.6480 (4)0.8394 (3)0.0802 (19)
H400.02720.67830.85840.096*
C230.2359 (3)0.3305 (3)0.6789 (3)0.0552 (13)
C70.1050 (3)0.0101 (3)0.7867 (2)0.0416 (10)
C150.0884 (4)0.0822 (4)0.9530 (3)0.0724 (15)
H150.11950.13680.94920.087*
C270.0685 (4)0.5614 (3)0.8097 (3)0.0639 (14)
H270.01120.53360.80940.077*
C10.3063 (3)0.0867 (3)0.7844 (3)0.0591 (13)
H1A0.34540.13930.79040.071*
H1B0.27400.09070.73290.071*
C310.2287 (4)0.5576 (4)0.7824 (3)0.0664 (15)
H310.27970.52790.76310.080*
C210.2212 (4)0.3231 (3)0.8259 (3)0.0664 (16)
H21A0.27360.28280.82510.080*
H21B0.23220.36660.86840.080*
C120.0692 (3)0.0920 (3)0.7631 (3)0.0626 (13)
H120.09390.14450.78510.075*
C300.2368 (5)0.6445 (4)0.8135 (4)0.089 (2)
H300.29410.67220.81570.107*
C140.0050 (3)0.0797 (4)0.9487 (3)0.0546 (13)
H140.03720.13320.94290.066*
C110.0027 (3)0.0980 (3)0.7074 (3)0.0723 (15)
H110.02610.15380.69230.087*
C170.0901 (4)0.0775 (4)0.9669 (3)0.0722 (15)
H170.12290.13070.97210.087*
C340.0177 (4)0.5610 (4)0.6019 (3)0.0717 (16)
H340.03470.52860.61430.086*
C390.1772 (4)0.3359 (4)0.5424 (3)0.0643 (15)
H39A0.16950.38080.50060.077*
H39B0.23060.30000.53030.077*
C220.0637 (4)0.3313 (4)0.8440 (3)0.0701 (16)
H22A0.07320.37530.88630.084*
H22B0.00890.29710.85540.084*
C350.0098 (5)0.6486 (4)0.5756 (4)0.088 (2)
H350.04770.67560.57040.106*
C90.0044 (3)0.0610 (3)0.6977 (3)0.0631 (13)
H90.02920.11320.67530.076*
C160.1361 (4)0.0036 (5)0.9628 (3)0.0780 (17)
H160.19960.00500.96680.094*
C410.0865 (6)0.6952 (4)0.5574 (4)0.092 (2)
H410.08070.75450.54030.111*
C360.1708 (5)0.6584 (4)0.5633 (3)0.0835 (19)
H360.22240.69090.54890.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.071 (2)0.065 (2)0.0495 (19)0.0027 (19)0.0192 (15)0.0024 (17)
N30.045 (2)0.041 (2)0.042 (2)0.0059 (18)0.0019 (18)0.0072 (17)
O60.082 (3)0.052 (2)0.081 (3)0.000 (2)0.004 (2)0.0136 (18)
O40.0484 (18)0.0577 (19)0.069 (2)0.0152 (16)0.0124 (16)0.0025 (16)
N70.046 (2)0.045 (2)0.058 (3)0.001 (2)0.002 (2)0.008 (2)
C320.063 (3)0.037 (3)0.051 (3)0.007 (3)0.013 (2)0.001 (2)
O30.063 (2)0.059 (2)0.067 (2)0.0252 (18)0.0222 (17)0.0044 (16)
O50.081 (3)0.058 (2)0.073 (3)0.011 (2)0.003 (2)0.0200 (18)
N20.045 (2)0.045 (2)0.042 (2)0.0077 (18)0.0079 (18)0.0072 (17)
O80.058 (2)0.054 (2)0.104 (3)0.016 (2)0.0178 (19)0.021 (2)
N50.058 (3)0.036 (2)0.052 (2)0.008 (2)0.002 (2)0.0065 (19)
C40.052 (3)0.036 (3)0.057 (3)0.001 (2)0.020 (3)0.009 (2)
O70.065 (2)0.052 (2)0.112 (3)0.0186 (19)0.007 (2)0.010 (2)
N10.046 (2)0.044 (2)0.044 (2)0.0087 (17)0.0023 (18)0.0031 (18)
O10.0510 (19)0.081 (3)0.078 (2)0.0008 (19)0.0118 (16)0.008 (2)
C330.059 (3)0.042 (3)0.045 (3)0.003 (3)0.010 (2)0.001 (2)
N60.049 (2)0.048 (2)0.066 (3)0.006 (2)0.014 (2)0.001 (2)
N80.049 (2)0.053 (2)0.055 (3)0.014 (2)0.004 (2)0.010 (2)
C30.040 (3)0.037 (3)0.047 (3)0.001 (2)0.015 (2)0.001 (2)
C80.059 (3)0.056 (3)0.045 (3)0.009 (2)0.011 (2)0.008 (2)
C130.042 (2)0.051 (3)0.036 (2)0.000 (3)0.0019 (18)0.003 (2)
C100.061 (3)0.080 (4)0.056 (3)0.006 (3)0.027 (3)0.007 (3)
N40.056 (2)0.043 (2)0.041 (2)0.0051 (19)0.0121 (19)0.0018 (18)
C190.069 (3)0.055 (3)0.049 (3)0.000 (3)0.007 (3)0.009 (2)
C260.044 (3)0.042 (3)0.054 (3)0.001 (2)0.007 (2)0.003 (2)
C60.042 (2)0.037 (2)0.039 (2)0.000 (3)0.007 (2)0.002 (2)
C50.043 (2)0.041 (2)0.040 (2)0.000 (2)0.0047 (19)0.000 (2)
C250.046 (3)0.038 (3)0.052 (3)0.002 (2)0.005 (2)0.002 (2)
C240.042 (3)0.039 (3)0.085 (4)0.002 (3)0.004 (3)0.017 (3)
C20.054 (3)0.059 (3)0.064 (3)0.005 (3)0.003 (3)0.012 (3)
C200.077 (3)0.055 (3)0.048 (3)0.004 (3)0.016 (3)0.009 (2)
C380.066 (4)0.074 (4)0.071 (4)0.012 (3)0.005 (3)0.028 (3)
C290.130 (6)0.038 (3)0.102 (5)0.006 (4)0.066 (5)0.003 (3)
C370.065 (4)0.048 (3)0.070 (4)0.001 (3)0.002 (3)0.007 (3)
C180.053 (3)0.065 (4)0.060 (4)0.005 (3)0.005 (3)0.008 (3)
C400.111 (5)0.048 (3)0.080 (4)0.012 (3)0.026 (4)0.014 (3)
C230.047 (3)0.048 (3)0.070 (4)0.003 (3)0.005 (3)0.006 (3)
C70.046 (2)0.046 (3)0.033 (2)0.000 (2)0.0050 (18)0.000 (2)
C150.059 (4)0.096 (5)0.061 (3)0.023 (3)0.009 (3)0.004 (3)
C270.078 (4)0.047 (3)0.066 (3)0.005 (3)0.014 (3)0.010 (3)
C10.058 (3)0.067 (3)0.052 (3)0.009 (3)0.001 (3)0.002 (3)
C310.067 (4)0.064 (3)0.067 (4)0.015 (3)0.017 (3)0.008 (3)
C210.072 (4)0.053 (3)0.072 (4)0.012 (3)0.022 (3)0.001 (3)
C120.061 (3)0.053 (3)0.072 (3)0.006 (2)0.024 (3)0.007 (3)
C300.111 (6)0.051 (4)0.101 (5)0.030 (4)0.060 (5)0.016 (3)
C140.049 (3)0.067 (4)0.047 (3)0.012 (3)0.004 (2)0.005 (2)
C110.080 (4)0.059 (3)0.076 (4)0.008 (3)0.024 (3)0.009 (3)
C170.052 (3)0.094 (4)0.070 (4)0.017 (3)0.006 (3)0.009 (3)
C340.069 (4)0.060 (4)0.085 (4)0.005 (3)0.028 (3)0.006 (3)
C390.065 (4)0.059 (3)0.069 (4)0.000 (3)0.009 (3)0.006 (3)
C220.091 (4)0.059 (4)0.061 (4)0.003 (3)0.006 (3)0.013 (3)
C350.087 (5)0.070 (4)0.105 (5)0.026 (4)0.034 (4)0.004 (4)
C90.073 (3)0.061 (3)0.054 (3)0.007 (3)0.017 (3)0.001 (3)
C160.044 (3)0.124 (5)0.065 (4)0.013 (4)0.001 (2)0.007 (4)
C410.133 (7)0.056 (4)0.086 (5)0.018 (5)0.023 (5)0.016 (3)
C360.103 (5)0.061 (4)0.088 (5)0.002 (4)0.005 (4)0.007 (3)
Geometric parameters (Å, º) top
O2—C201.426 (5)C19—H19A0.9700
O2—C191.425 (5)C19—H19B0.9700
N3—C31.374 (5)C26—C251.583 (5)
N3—C191.446 (5)C6—C51.583 (5)
N3—C61.467 (5)C5—C71.512 (5)
O6—C221.418 (6)C2—H2A0.9700
O6—C211.426 (6)C2—H2B0.9700
O4—C31.209 (4)C20—H20A0.9700
N7—C231.399 (6)C20—H20B0.9700
N7—C391.426 (6)C38—H38A0.9700
N7—C261.463 (6)C38—H38B0.9700
C32—C271.373 (7)C29—C301.356 (8)
C32—C311.393 (7)C29—C401.377 (9)
C32—C251.504 (6)C29—H290.9300
O3—C41.226 (5)C37—C361.371 (7)
O5—C381.409 (6)C37—H370.9300
O5—C391.420 (6)C18—C171.361 (7)
N2—C41.373 (5)C18—H180.9300
N2—C21.448 (5)C40—C271.385 (7)
N2—C51.463 (5)C40—H400.9300
O8—C241.217 (5)C7—C121.379 (5)
N5—C241.391 (5)C15—C141.364 (7)
N5—C221.447 (6)C15—C161.372 (7)
N5—C251.454 (6)C15—H150.9300
C4—N41.374 (6)C27—H270.9300
O7—C231.214 (5)C1—H1A0.9700
N1—C31.378 (5)C1—H1B0.9700
N1—C11.439 (5)C31—C301.396 (7)
N1—C51.458 (5)C31—H310.9300
O1—C21.409 (5)C21—H21A0.9700
O1—C11.408 (5)C21—H21B0.9700
C33—C341.380 (6)C12—C111.383 (5)
C33—C371.383 (6)C12—H120.9300
C33—C261.507 (6)C30—H300.9300
N6—C231.373 (6)C14—H140.9300
N6—C211.449 (6)C11—H110.9300
N6—C251.467 (5)C17—C161.381 (7)
N8—C241.375 (6)C17—H170.9300
N8—C381.430 (6)C34—C351.379 (8)
N8—C261.452 (5)C34—H340.9300
C8—C91.377 (5)C39—H39A0.9700
C8—C71.372 (5)C39—H39B0.9700
C8—H80.9300C22—H22A0.9700
C13—C141.387 (6)C22—H22B0.9700
C13—C181.393 (6)C35—C411.357 (8)
C13—C61.500 (6)C35—H350.9300
C10—C111.357 (6)C9—H90.9300
C10—C91.377 (6)C16—H160.9300
C10—H100.9300C41—C361.345 (8)
N4—C201.447 (5)C41—H410.9300
N4—C61.462 (5)C36—H360.9300
C20—O2—C19109.7 (3)N4—C20—H20B109.3
C3—N3—C19120.5 (3)H20A—C20—H20B108.0
C3—N3—C6112.0 (3)O5—C38—N8110.9 (4)
C19—N3—C6114.9 (3)O5—C38—H38A109.5
C22—O6—C21109.6 (4)N8—C38—H38A109.5
C23—N7—C39117.4 (4)O5—C38—H38B109.5
C23—N7—C26110.6 (4)N8—C38—H38B109.5
C39—N7—C26114.4 (4)H38A—C38—H38B108.0
C27—C32—C31119.7 (5)C30—C29—C40119.9 (6)
C27—C32—C25120.4 (4)C30—C29—H29120.1
C31—C32—C25119.6 (5)C40—C29—H29120.1
C38—O5—C39109.7 (4)C36—C37—C33121.7 (5)
C4—N2—C2121.0 (4)C36—C37—H37119.1
C4—N2—C5111.6 (3)C33—C37—H37119.1
C2—N2—C5114.9 (3)C17—C18—C13120.5 (5)
C24—N5—C22120.5 (4)C17—C18—H18119.7
C24—N5—C25110.9 (4)C13—C18—H18119.7
C22—N5—C25115.6 (4)C29—C40—C27119.9 (6)
O3—C4—N2126.1 (5)C29—C40—H40120.0
O3—C4—N4125.7 (4)C27—C40—H40120.0
N2—C4—N4108.1 (4)O7—C23—N6126.0 (5)
C3—N1—C1121.3 (3)O7—C23—N7126.5 (5)
C3—N1—C5112.6 (3)N6—C23—N7107.3 (4)
C1—N1—C5115.3 (3)C8—C7—C12118.0 (4)
C2—O1—C1111.1 (3)C8—C7—C5122.0 (4)
C34—C33—C37117.9 (4)C12—C7—C5120.0 (4)
C34—C33—C26120.8 (5)C14—C15—C16119.4 (5)
C37—C33—C26120.9 (4)C14—C15—H15120.3
C23—N6—C21122.6 (4)C16—C15—H15120.3
C23—N6—C25112.0 (4)C32—C27—C40120.5 (6)
C21—N6—C25114.7 (4)C32—C27—H27119.7
C24—N8—C38121.2 (4)C40—C27—H27119.7
C24—N8—C26111.8 (4)O1—C1—N1110.6 (4)
C38—N8—C26116.9 (4)O1—C1—H1A109.5
O4—C3—N3126.6 (4)N1—C1—H1A109.5
O4—C3—N1126.2 (4)O1—C1—H1B109.5
N3—C3—N1107.0 (3)N1—C1—H1B109.5
C9—C8—C7121.0 (4)H1A—C1—H1B108.1
C9—C8—H8119.5C32—C31—C30118.7 (6)
C7—C8—H8119.5C32—C31—H31120.7
C14—C13—C18118.1 (4)C30—C31—H31120.6
C14—C13—C6120.3 (4)O6—C21—N6111.4 (4)
C18—C13—C6121.5 (4)O6—C21—H21A109.4
C11—C10—C9120.1 (4)N6—C21—H21A109.3
C11—C10—H10119.9O6—C21—H21B109.4
C9—C10—H10119.9N6—C21—H21B109.4
C4—N4—C20121.2 (4)H21A—C21—H21B108.0
C4—N4—C6111.6 (3)C11—C12—C7121.4 (4)
C20—N4—C6115.2 (3)C11—C12—H12119.3
O2—C19—N3110.9 (3)C7—C12—H12119.3
O2—C19—H19A109.5C29—C30—C31121.3 (6)
N3—C19—H19A109.5C29—C30—H30119.4
O2—C19—H19B109.5C31—C30—H30119.4
N3—C19—H19B109.5C15—C14—C13121.5 (5)
H19A—C19—H19B108.0C15—C14—H14119.3
N8—C26—N7109.6 (3)C13—C14—H14119.3
N8—C26—C33111.6 (4)C10—C11—C12119.6 (4)
N7—C26—C33112.8 (4)C10—C11—H11120.2
N8—C26—C25103.1 (4)C12—C11—H11120.2
N7—C26—C25102.9 (3)C18—C17—C16120.2 (5)
C33—C26—C25116.0 (4)C18—C17—H17119.9
N4—C6—N3109.1 (3)C16—C17—H17119.9
N4—C6—C13113.2 (3)C35—C34—C33120.2 (6)
N3—C6—C13113.5 (3)C35—C34—H34119.9
N4—C6—C5102.7 (3)C33—C34—H34119.9
N3—C6—C5102.5 (3)O5—C39—N7113.1 (4)
C13—C6—C5114.8 (3)O5—C39—H39A108.9
N1—C5—N2108.6 (3)N7—C39—H39A108.9
N1—C5—C7112.2 (3)O5—C39—H39B109.0
N2—C5—C7112.9 (3)N7—C39—H39B109.0
N1—C5—C6102.3 (3)H39A—C39—H39B107.8
N2—C5—C6102.6 (3)O6—C22—N5110.3 (4)
C7—C5—C6117.2 (3)O6—C22—H22A109.6
N5—C25—N6109.0 (3)N5—C22—H22A109.6
N5—C25—C32113.3 (4)O6—C22—H22B109.6
N6—C25—C32112.3 (4)N5—C22—H22B109.6
N5—C25—C26103.0 (3)H22A—C22—H22B108.1
N6—C25—C26102.6 (3)C41—C35—C34119.5 (6)
C32—C25—C26115.7 (4)C41—C35—H35120.2
O8—C24—N8126.7 (5)C34—C35—H35120.2
O8—C24—N5124.9 (5)C8—C9—C10119.9 (4)
N8—C24—N5108.2 (4)C8—C9—H9120.1
O1—C2—N2110.9 (4)C10—C9—H9120.1
O1—C2—H2A109.5C15—C16—C17120.3 (5)
N2—C2—H2A109.5C15—C16—H16119.9
O1—C2—H2B109.5C17—C16—H16119.9
N2—C2—H2B109.5C36—C41—C35122.1 (6)
H2A—C2—H2B108.0C36—C41—H41119.0
O2—C20—N4111.5 (3)C35—C41—H41119.0
O2—C20—H20A109.3C41—C36—C37118.5 (6)
N4—C20—H20A109.3C41—C36—H36120.7
O2—C20—H20B109.3C37—C36—H36120.7
C2—N2—C4—O324.0 (6)C31—C32—C25—N5158.4 (4)
C5—N2—C4—O3164.0 (4)C27—C32—C25—N6151.2 (4)
C2—N2—C4—N4158.9 (4)C31—C32—C25—N634.4 (6)
C5—N2—C4—N418.9 (4)C27—C32—C25—C2691.4 (5)
C19—N3—C3—O426.4 (6)C31—C32—C25—C2683.0 (5)
C6—N3—C3—O4166.1 (4)N8—C26—C25—N54.0 (4)
C19—N3—C3—N1159.5 (3)N7—C26—C25—N5118.0 (3)
C6—N3—C3—N119.7 (4)C33—C26—C25—N5118.3 (4)
C1—N1—C3—O424.4 (6)N8—C26—C25—N6109.2 (3)
C5—N1—C3—O4167.0 (4)N7—C26—C25—N64.8 (4)
C1—N1—C3—N3161.4 (4)C33—C26—C25—N6128.5 (4)
C5—N1—C3—N318.8 (4)N8—C26—C25—C32128.1 (4)
O3—C4—N4—C2023.6 (7)N7—C26—C25—C32117.9 (4)
N2—C4—N4—C20159.2 (3)C33—C26—C25—C325.8 (5)
O3—C4—N4—C6164.5 (4)C38—N8—C24—O823.3 (7)
N2—C4—N4—C618.3 (4)C26—N8—C24—O8167.7 (4)
C20—O2—C19—N359.5 (5)C38—N8—C24—N5160.0 (4)
C3—N3—C19—O283.4 (5)C26—N8—C24—N515.6 (5)
C6—N3—C19—O255.3 (5)C22—N5—C24—O825.2 (7)
C24—N8—C26—N7102.2 (4)C25—N5—C24—O8164.8 (4)
C38—N8—C26—N743.8 (5)C22—N5—C24—N8158.1 (4)
C24—N8—C26—C33132.0 (4)C25—N5—C24—N818.5 (5)
C38—N8—C26—C3382.0 (5)C1—O1—C2—N258.4 (5)
C24—N8—C26—C256.8 (5)C4—N2—C2—O185.2 (5)
C38—N8—C26—C25152.8 (4)C5—N2—C2—O153.6 (4)
C23—N7—C26—N892.6 (4)C19—O2—C20—N458.6 (5)
C39—N7—C26—N842.7 (5)C4—N4—C20—O286.3 (5)
C23—N7—C26—C33142.3 (4)C6—N4—C20—O253.3 (5)
C39—N7—C26—C3382.5 (5)C39—O5—C38—N857.4 (5)
C23—N7—C26—C2516.6 (4)C24—N8—C38—O590.0 (6)
C39—N7—C26—C25151.8 (4)C26—N8—C38—O552.7 (6)
C34—C33—C26—N828.2 (6)C34—C33—C37—C361.7 (7)
C37—C33—C26—N8158.7 (4)C26—C33—C37—C36174.9 (5)
C34—C33—C26—N7152.3 (4)C14—C13—C18—C172.1 (6)
C37—C33—C26—N734.7 (6)C6—C13—C18—C17173.3 (4)
C34—C33—C26—C2589.4 (5)C30—C29—C40—C270.6 (9)
C37—C33—C26—C2583.6 (5)C21—N6—C23—O722.5 (7)
C4—N4—C6—N397.8 (4)C25—N6—C23—O7165.0 (5)
C20—N4—C6—N345.6 (4)C21—N6—C23—N7161.8 (4)
C4—N4—C6—C13134.8 (4)C25—N6—C23—N719.2 (5)
C20—N4—C6—C1381.8 (4)C39—N7—C23—O727.9 (7)
C4—N4—C6—C510.4 (4)C26—N7—C23—O7161.6 (5)
C20—N4—C6—C5153.8 (3)C39—N7—C23—N6156.4 (4)
C3—N3—C6—N495.5 (4)C26—N7—C23—N622.6 (5)
C19—N3—C6—N446.6 (4)C9—C8—C7—C120.6 (6)
C3—N3—C6—C13137.2 (3)C9—C8—C7—C5178.8 (4)
C19—N3—C6—C1380.6 (4)N1—C5—C7—C8151.5 (4)
C3—N3—C6—C512.8 (4)N2—C5—C7—C828.4 (5)
C19—N3—C6—C5155.0 (3)C6—C5—C7—C890.6 (5)
C14—C13—C6—N434.0 (5)N1—C5—C7—C1230.2 (5)
C18—C13—C6—N4150.7 (4)N2—C5—C7—C12153.4 (4)
C14—C13—C6—N3159.1 (4)C6—C5—C7—C1287.7 (5)
C18—C13—C6—N325.6 (5)C31—C32—C27—C401.0 (7)
C14—C13—C6—C583.5 (5)C25—C32—C27—C40173.5 (5)
C18—C13—C6—C591.8 (5)C29—C40—C27—C320.6 (8)
C3—N1—C5—N297.7 (4)C2—O1—C1—N158.8 (5)
C1—N1—C5—N247.3 (4)C3—N1—C1—O187.0 (5)
C3—N1—C5—C7136.8 (3)C5—N1—C1—O154.6 (4)
C1—N1—C5—C778.3 (4)C27—C32—C31—C300.1 (7)
C3—N1—C5—C610.4 (4)C25—C32—C31—C30174.3 (4)
C1—N1—C5—C6155.3 (3)C22—O6—C21—N659.5 (5)
C4—N2—C5—N196.0 (4)C23—N6—C21—O688.0 (5)
C2—N2—C5—N146.6 (4)C25—N6—C21—O653.6 (5)
C4—N2—C5—C7138.9 (3)C8—C7—C12—C110.3 (7)
C2—N2—C5—C778.5 (4)C5—C7—C12—C11178.6 (4)
C4—N2—C5—C611.8 (4)C40—C29—C30—C311.4 (9)
C2—N2—C5—C6154.4 (3)C32—C31—C30—C291.1 (8)
N4—C6—C5—N1111.8 (3)C16—C15—C14—C131.0 (7)
N3—C6—C5—N11.4 (3)C18—C13—C14—C151.5 (6)
C13—C6—C5—N1124.9 (3)C6—C13—C14—C15174.0 (4)
N4—C6—C5—N20.8 (3)C9—C10—C11—C120.0 (8)
N3—C6—C5—N2114.0 (3)C7—C12—C11—C100.0 (8)
C13—C6—C5—N2122.5 (3)C13—C18—C17—C162.3 (7)
N4—C6—C5—C7125.1 (3)C37—C33—C34—C350.3 (7)
N3—C6—C5—C7121.7 (3)C26—C33—C34—C35173.5 (5)
C13—C6—C5—C71.8 (5)C38—O5—C39—N758.8 (5)
C24—N5—C25—N694.9 (4)C23—N7—C39—O579.7 (5)
C22—N5—C25—N646.8 (5)C26—N7—C39—O552.4 (5)
C24—N5—C25—C32139.2 (4)C21—O6—C22—N559.7 (5)
C22—N5—C25—C3279.1 (5)C24—N5—C22—O682.3 (5)
C24—N5—C25—C2613.5 (4)C25—N5—C22—O655.5 (5)
C22—N5—C25—C26155.2 (4)C33—C34—C35—C410.2 (9)
C23—N6—C25—N5100.2 (4)C7—C8—C9—C100.5 (7)
C21—N6—C25—N545.5 (5)C11—C10—C9—C80.3 (8)
C23—N6—C25—C32133.4 (4)C14—C15—C16—C171.2 (7)
C21—N6—C25—C3281.0 (5)C18—C17—C16—C151.8 (7)
C23—N6—C25—C268.5 (5)C34—C35—C41—C360.7 (10)
C21—N6—C25—C26154.1 (4)C35—C41—C36—C372.1 (10)
C27—C32—C25—N527.1 (6)C33—C37—C36—C412.6 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O8i0.972.403.188 (5)138
C27—H27···O1ii0.932.303.208 (7)166
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC20H18N4O4
Mr378.39
Crystal system, space groupMonoclinic, Cc
Temperature (K)292
a, b, c (Å)14.558 (3), 14.870 (3), 16.711 (3)
β (°) 91.695 (3)
V3)3616.2 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.34 × 0.18 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13181, 3192, 1976
Rint0.103
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.079, 0.80
No. of reflections3192
No. of parameters505
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O8i0.972.403.188 (5)138.0
C27—H27···O1ii0.932.303.208 (7)166.2
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+1/2, z.
 

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