PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1922.
Published online 2010 July 7. doi:  10.1107/S1600536810025614
PMCID: PMC3007303

1-Benzyl-3-methyl­quinoxalin-2(1H)-one

Abstract

The asymmetric unit of the title compound, C16H14N2O, contains three independent mol­ecules. The dihedral angles between the quinoxaline and phenyl planes in the three mol­ecules are 82.58 (8), 85.66 (9) and 85.36 (9)°. The crystal packing is stabilized by C—H(...)O and C—H(...)N hydrogen bonds.

Related literature

For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 [triangle]); Abasolo et al. (1987 [triangle]); Rodrigo et al. (2002 [triangle]); Jampilek et al. (2005 [triangle]); Sashidhara et al. (2009 [triangle]); Watkins et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1922-scheme1.jpg

Experimental

Crystal data

  • C16H14N2O
  • M r = 250.29
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1922-efi1.jpg
  • a = 7.4433 (2) Å
  • b = 17.5444 (5) Å
  • c = 18.0598 (7) Å
  • α = 118.034 (2)°
  • β = 100.217 (2)°
  • γ = 92.726 (1)°
  • V = 2025.27 (11) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.25 × 0.21 × 0.15 mm

Data collection

  • Bruker X8 APEXII CCD area-detector diffractometer
  • 46425 measured reflections
  • 9750 independent reflections
  • 6445 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.166
  • S = 1.09
  • 9750 reflections
  • 516 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025614/pv2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025614/pv2301Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the CNRST of Morocco for making this work possible.

supplementary crystallographic information

Comment

Quinoxaline derivatives are an important class of nitrogen containing heterocycles in medicinal chemistry. They exhibit antimicrobial (Kleim et al., 1995), antitumor (Abasolo et al., 1987), and antituberculous activity (Rodrigo et al., 2002]. They also exhibit antifungal, herbicidal, antidyslipidemic and antioxidative activities (Jampilek et al., 2005; Sashidhara et al., 2009; Watkins et al., 2009). In this paper, the synthesis and crystal structure of the title compound is presented.

The asymmetric unit of the title compound contains three independent molecules (Fig. 1). The dihedral angles between the quinoxaline and phenyl planes in the three molecules are 82.58 (8), 85.66 (9) and 85.36 (9)°. The crystal structure is devoid of classical hydrogen bonds. However, the crystal packing is stabilized by C—H···O and C—H···N hydrogen bonds (Tab. 1 & Fig. 2).

Experimental

To a solution of 3-methylquinoxali-2(1H)-one (1 g) in 20 ml of dimethylformamide were added benzylchloride (0.72 ml), K2CO3 (0.90 g) and catalytic amont of tetrabutylammonium bromide. The mixture was stirred at room temperature for 24 h. The solvent was removed under reduce pressure and the residue was crystallized in ethanol to afford the crystals of the title compound which were suitable for X-ray analysis.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl), 0.98Å methine or 0.93 Å (aromatic) with Uĩso(H) = 1.2Ueq(C) or 1.5Ueq(methyl). The H-atoms of the methyl groups C21 and C31 were disordered over six sites each with 0.5 site occupancy factors. A search for solvent-accessible voids in the crystal structure using PLATON (Spek, 2009) showed solvent accessible voids of 110 Å3. However, the refinement showed no electron density in the voids. This indicates that the crystal lost the solvent of crystallization by the time it was used for data collection, without collapse of the crystal lattice.

Figures

Fig. 1.
Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
Crystal packing of the title compound viewed down the c- axis; H-atoms not involved in H-bonds have been omitted for clarity.

Crystal data

C16H14N2OZ = 6
Mr = 250.29F(000) = 792
Triclinic, P1Dx = 1.231 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4433 (2) ÅCell parameters from 4372 reflections
b = 17.5444 (5) Åθ = 2.3–27.3°
c = 18.0598 (7) ŵ = 0.08 mm1
α = 118.034 (2)°T = 296 K
β = 100.217 (2)°Prism, yellow
γ = 92.726 (1)°0.25 × 0.21 × 0.15 mm
V = 2025.27 (11) Å3

Data collection

Bruker X8 APEXII CCD area-detector diffractometer6445 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
graphiteθmax = 28.0°, θmin = 1.3°
[var phi] and ω scansh = −9→9
46425 measured reflectionsk = −23→23
9750 independent reflectionsl = −23→23

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.166w = 1/[σ2(Fo2) + (0.086P)2 + 0.196P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
9750 reflectionsΔρmax = 0.30 e Å3
516 parametersΔρmin = −0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0084 (16)

Special details

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of four sets of exposures; each set had a different [var phi] angle for the crystal and each exposure covered 0.5° in ω and 30 s in time. The crystal-to-detector distance was 37.5 mm.
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)

xyzUiso*/UeqOcc. (<1)
N110.28817 (17)0.61727 (8)0.12094 (8)0.0539 (3)
N120.24494 (17)0.50211 (9)−0.05373 (8)0.0535 (3)
N210.68069 (17)0.40186 (8)0.50730 (7)0.0473 (3)
N220.82004 (17)0.56626 (8)0.53631 (8)0.0535 (3)
N310.29515 (17)0.08130 (8)0.97102 (8)0.0497 (3)
N320.22062 (16)−0.00511 (8)1.06097 (8)0.0496 (3)
C3100.28440 (18)−0.00937 (9)0.93170 (9)0.0452 (3)
C3160.22919 (19)0.07835 (10)1.09571 (9)0.0485 (3)
C3170.2642 (2)0.12871 (10)1.05228 (10)0.0518 (4)
C3140.2368 (2)−0.14167 (10)0.94073 (10)0.0557 (4)
H3140.2116−0.16930.97160.067*
C3110.3100 (2)−0.05966 (11)0.84834 (10)0.0571 (4)
H3110.3340−0.03300.81640.069*
C3130.2644 (2)−0.19009 (11)0.85939 (11)0.0635 (4)
H3130.2595−0.25030.83520.076*
C3120.2996 (2)−0.14864 (12)0.81358 (11)0.0643 (5)
H3120.3167−0.18170.75800.077*
C3200.1937 (2)0.12140 (10)0.85582 (10)0.0562 (4)
C3190.3461 (2)0.12854 (12)0.92698 (12)0.0637 (4)
H31A0.45110.10630.90300.076*
H31B0.38470.18980.96920.076*
C310.2052 (3)0.12919 (12)1.18591 (11)0.0657 (4)
H31C0.18310.08991.20760.099*0.50
H31D0.10200.16011.18650.099*0.50
H31E0.31500.17021.22150.099*0.50
H31F0.21690.19021.20280.099*0.50
H31G0.29810.12001.22390.099*0.50
H31H0.08510.11001.18890.099*0.50
C3250.0106 (3)0.09773 (12)0.84936 (12)0.0684 (5)
H325−0.02290.08360.88920.082*
C323−0.0772 (4)0.11456 (15)0.72508 (15)0.0924 (7)
H323−0.16800.11150.68070.111*
C3210.2399 (3)0.14226 (12)0.79587 (13)0.0766 (5)
H3210.36300.15860.79920.092*
C3220.1044 (4)0.13898 (14)0.73145 (15)0.0938 (7)
H3220.13680.15350.69170.113*
C324−0.1241 (3)0.09471 (15)0.78441 (14)0.0856 (6)
H324−0.24760.07900.78100.103*
C2100.64496 (18)0.42088 (9)0.43991 (8)0.0420 (3)
C2150.71574 (19)0.50356 (9)0.45595 (9)0.0450 (3)
C2170.7903 (2)0.46041 (11)0.58679 (9)0.0532 (4)
C2110.54277 (19)0.36064 (10)0.35746 (9)0.0510 (3)
H2110.49670.30500.34580.061*
C2160.85465 (19)0.54651 (10)0.59690 (9)0.0521 (4)
C2120.5101 (2)0.38320 (12)0.29369 (10)0.0599 (4)
H2120.44230.34260.23900.072*
C2140.6798 (2)0.52521 (11)0.39025 (11)0.0573 (4)
H2140.72580.58050.40080.069*
C2130.5769 (2)0.46550 (13)0.30999 (11)0.0629 (4)
H2130.55230.48060.26670.075*
C2190.6009 (3)0.31832 (11)0.49568 (11)0.0613 (4)
H21A0.47330.30450.46430.074*
H21B0.60160.32400.55180.074*
C210.9649 (2)0.61360 (13)0.68370 (11)0.0733 (5)
H21C0.99900.66650.68260.110*0.50
H21D1.07440.59220.69850.110*0.50
H21E0.89230.62520.72580.110*0.50
H21F0.97810.58950.72200.110*0.50
H21G0.90270.66370.70610.110*0.50
H21H1.08480.63070.67880.110*0.50
C2200.7010 (3)0.24364 (10)0.44807 (10)0.0605 (4)
C2250.8727 (3)0.25573 (12)0.43371 (10)0.0639 (4)
H2250.92960.31190.45190.077*
C2240.9621 (3)0.18488 (14)0.39230 (12)0.0816 (6)
H2241.07810.19380.38280.098*
C2220.7101 (6)0.08964 (16)0.37896 (19)0.1197 (10)
H2220.65430.03320.36060.144*
C2230.8800 (5)0.10206 (16)0.36553 (15)0.1040 (9)
H2230.94020.05460.33830.125*
C2210.6180 (4)0.15941 (14)0.41957 (16)0.0984 (7)
H2210.50090.14970.42770.118*
C1150.21989 (19)0.47190 (9)0.00291 (9)0.0480 (3)
C1100.24117 (18)0.52774 (10)0.09044 (9)0.0474 (3)
C1160.2905 (2)0.58474 (11)−0.02376 (11)0.0555 (4)
C1170.3162 (2)0.64957 (10)0.06708 (11)0.0570 (4)
C1140.1692 (2)0.38238 (11)−0.03048 (12)0.0614 (4)
H1140.15280.3451−0.08930.074*
C1200.4972 (2)0.69464 (11)0.26728 (10)0.0568 (4)
C1110.2174 (2)0.49301 (13)0.14423 (11)0.0643 (4)
H1110.23340.52950.20320.077*
C1120.1700 (3)0.40430 (15)0.10900 (15)0.0759 (6)
H1120.15540.38120.14490.091*
C1250.6317 (2)0.64524 (12)0.23666 (12)0.0652 (4)
H1250.60740.60110.17960.078*
C1190.3077 (3)0.68063 (12)0.21185 (11)0.0708 (5)
H11A0.21670.66090.23400.085*
H11B0.28110.73610.21650.085*
C1130.1435 (3)0.34875 (13)0.02172 (16)0.0758 (5)
H1130.10850.2890−0.00120.091*
C110.3186 (3)0.61802 (15)−0.08384 (15)0.0822 (6)
H11C0.44640.6413−0.07120.123*
H11D0.24440.6632−0.07690.123*
H11E0.28310.5710−0.14210.123*
C1240.8032 (3)0.66059 (15)0.29001 (15)0.0790 (6)
H1240.89230.62600.26860.095*
C1220.7113 (4)0.77463 (18)0.40426 (13)0.0971 (8)
H1220.73790.81900.46130.117*
C1230.8427 (3)0.72538 (18)0.37299 (16)0.0909 (7)
H1230.95890.73600.40820.109*
C1210.5376 (3)0.75980 (13)0.35231 (11)0.0774 (5)
H1210.44850.79370.37470.093*
C3150.24616 (18)−0.05134 (9)0.97775 (9)0.0453 (3)
O30.2684 (2)0.20807 (7)1.08693 (8)0.0760 (4)
O20.8293 (2)0.44281 (9)0.64486 (8)0.0787 (4)
O10.3599 (2)0.72780 (8)0.09362 (10)0.0879 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N110.0469 (7)0.0550 (7)0.0483 (7)0.0114 (5)0.0066 (5)0.0171 (6)
N120.0517 (7)0.0603 (8)0.0489 (7)0.0140 (6)0.0127 (5)0.0259 (6)
N210.0511 (7)0.0470 (6)0.0435 (6)0.0113 (5)0.0137 (5)0.0205 (5)
N220.0476 (7)0.0494 (7)0.0524 (7)0.0056 (5)0.0138 (5)0.0151 (6)
N310.0479 (7)0.0470 (7)0.0509 (7)−0.0003 (5)0.0031 (5)0.0246 (6)
N320.0458 (6)0.0501 (7)0.0479 (7)0.0031 (5)0.0041 (5)0.0224 (6)
C3100.0336 (6)0.0473 (7)0.0459 (7)0.0031 (5)0.0010 (5)0.0186 (6)
C3160.0390 (7)0.0520 (8)0.0447 (7)0.0048 (6)0.0010 (6)0.0189 (6)
C3170.0483 (8)0.0447 (8)0.0525 (8)0.0058 (6)−0.0002 (6)0.0198 (7)
C3140.0514 (8)0.0469 (8)0.0596 (9)0.0047 (6)0.0000 (7)0.0229 (7)
C3110.0469 (8)0.0693 (10)0.0509 (9)0.0095 (7)0.0082 (6)0.0268 (8)
C3130.0579 (9)0.0472 (8)0.0626 (10)0.0095 (7)−0.0029 (8)0.0140 (8)
C3120.0512 (9)0.0676 (11)0.0486 (9)0.0160 (8)0.0039 (7)0.0097 (8)
C3200.0682 (10)0.0431 (8)0.0592 (9)0.0066 (7)0.0138 (8)0.0269 (7)
C3190.0604 (10)0.0614 (10)0.0710 (11)−0.0056 (8)0.0077 (8)0.0374 (9)
C310.0625 (10)0.0682 (11)0.0505 (9)0.0096 (8)0.0087 (7)0.0176 (8)
C3250.0663 (11)0.0806 (12)0.0669 (11)0.0178 (9)0.0156 (8)0.0421 (10)
C3230.124 (2)0.0773 (14)0.0761 (14)0.0410 (14)0.0033 (13)0.0420 (11)
C3210.1011 (15)0.0621 (11)0.0762 (12)−0.0015 (10)0.0203 (11)0.0425 (10)
C3220.149 (2)0.0725 (13)0.0768 (14)0.0162 (14)0.0190 (14)0.0522 (12)
C3240.0730 (13)0.0944 (15)0.0890 (15)0.0303 (11)0.0106 (11)0.0454 (13)
C2100.0379 (6)0.0459 (7)0.0407 (7)0.0132 (5)0.0134 (5)0.0177 (6)
C2150.0408 (7)0.0458 (7)0.0452 (7)0.0125 (6)0.0148 (6)0.0173 (6)
C2170.0488 (8)0.0673 (10)0.0414 (8)0.0208 (7)0.0129 (6)0.0227 (7)
C2110.0434 (7)0.0507 (8)0.0458 (8)0.0066 (6)0.0073 (6)0.0140 (7)
C2160.0410 (7)0.0567 (9)0.0443 (8)0.0106 (6)0.0125 (6)0.0118 (7)
C2120.0471 (8)0.0801 (12)0.0420 (8)0.0194 (8)0.0070 (6)0.0214 (8)
C2140.0626 (9)0.0594 (9)0.0636 (10)0.0213 (8)0.0262 (8)0.0357 (8)
C2130.0635 (10)0.0858 (12)0.0538 (9)0.0310 (9)0.0205 (8)0.0413 (9)
C2190.0725 (11)0.0584 (9)0.0606 (10)0.0103 (8)0.0242 (8)0.0318 (8)
C210.0546 (10)0.0806 (12)0.0495 (9)0.0060 (8)0.0045 (7)0.0066 (8)
C2200.0866 (12)0.0531 (9)0.0464 (8)0.0136 (8)0.0136 (8)0.0281 (7)
C2250.0734 (11)0.0629 (10)0.0484 (9)0.0207 (8)0.0055 (8)0.0233 (8)
C2240.0912 (14)0.0869 (15)0.0557 (10)0.0400 (12)0.0099 (9)0.0259 (10)
C2220.195 (3)0.0580 (13)0.112 (2)0.0256 (17)0.057 (2)0.0380 (13)
C2230.166 (3)0.0746 (15)0.0710 (14)0.0575 (17)0.0278 (16)0.0313 (12)
C2210.142 (2)0.0606 (12)0.1010 (17)0.0127 (13)0.0490 (16)0.0386 (12)
C1150.0429 (7)0.0512 (8)0.0516 (8)0.0139 (6)0.0087 (6)0.0265 (7)
C1100.0382 (7)0.0557 (8)0.0485 (8)0.0123 (6)0.0062 (6)0.0262 (7)
C1160.0470 (8)0.0649 (10)0.0633 (10)0.0120 (7)0.0133 (7)0.0375 (8)
C1170.0477 (8)0.0505 (9)0.0682 (10)0.0075 (7)0.0083 (7)0.0268 (8)
C1140.0579 (9)0.0512 (9)0.0678 (10)0.0137 (7)0.0070 (8)0.0250 (8)
C1200.0617 (9)0.0572 (9)0.0477 (8)0.0030 (7)0.0102 (7)0.0237 (7)
C1110.0510 (9)0.0926 (13)0.0583 (10)0.0156 (8)0.0073 (7)0.0451 (10)
C1120.0582 (10)0.0997 (15)0.1035 (16)0.0136 (10)0.0114 (10)0.0784 (14)
C1250.0562 (9)0.0684 (11)0.0665 (10)0.0052 (8)0.0084 (8)0.0316 (9)
C1190.0623 (10)0.0692 (11)0.0550 (10)0.0195 (8)0.0124 (8)0.0091 (8)
C1130.0636 (11)0.0625 (11)0.1107 (17)0.0117 (8)0.0063 (10)0.0540 (12)
C110.0773 (13)0.1012 (15)0.0964 (15)0.0114 (11)0.0272 (11)0.0683 (13)
C1240.0596 (11)0.0971 (15)0.0982 (16)0.0023 (10)0.0034 (10)0.0674 (13)
C1220.1140 (19)0.1139 (19)0.0466 (10)−0.0243 (15)−0.0085 (11)0.0383 (11)
C1230.0792 (14)0.128 (2)0.0820 (15)−0.0175 (14)−0.0125 (12)0.0770 (16)
C1210.0951 (14)0.0802 (13)0.0491 (10)0.0050 (10)0.0163 (9)0.0259 (9)
C3150.0355 (6)0.0461 (7)0.0466 (8)0.0026 (5)−0.0001 (5)0.0199 (6)
O30.0989 (10)0.0443 (6)0.0733 (8)0.0121 (6)0.0078 (7)0.0233 (6)
O20.0898 (9)0.0995 (10)0.0531 (7)0.0288 (7)0.0113 (6)0.0425 (7)
O10.0865 (10)0.0527 (7)0.1109 (11)−0.0007 (6)0.0136 (8)0.0328 (7)

Geometric parameters (Å, °)

N11—C1171.375 (2)C212—C2131.378 (3)
N11—C1101.3996 (19)C212—H2120.9300
N11—C1191.462 (2)C214—C2131.374 (2)
N12—C1161.288 (2)C214—H2140.9300
N12—C1151.3891 (19)C213—H2130.9300
N21—C2171.3784 (19)C219—C2201.507 (2)
N21—C2101.3925 (18)C219—H21A0.9700
N21—C2191.459 (2)C219—H21B0.9700
N22—C2161.284 (2)C21—H21C0.9600
N22—C2151.3920 (19)C21—H21D0.9600
N31—C3171.374 (2)C21—H21E0.9600
N31—C3101.3954 (18)C21—H21F0.9600
N31—C3191.470 (2)C21—H21G0.9600
N32—C3161.2866 (19)C21—H21H0.9600
N32—C3151.3868 (18)C220—C2251.375 (3)
C310—C3111.397 (2)C220—C2211.384 (3)
C310—C3151.398 (2)C225—C2241.388 (2)
C316—C3171.472 (2)C225—H2250.9300
C316—C311.495 (2)C224—C2231.367 (4)
C317—O31.2251 (18)C224—H2240.9300
C314—C3131.369 (2)C222—C2231.355 (4)
C314—C3151.393 (2)C222—C2211.386 (4)
C314—H3140.9300C222—H2220.9300
C311—C3121.374 (2)C223—H2230.9300
C311—H3110.9300C221—H2210.9300
C313—C3121.381 (3)C115—C1101.387 (2)
C313—H3130.9300C115—C1141.395 (2)
C312—H3120.9300C110—C1111.398 (2)
C320—C3251.374 (3)C116—C1171.462 (2)
C320—C3211.384 (2)C116—C111.492 (2)
C320—C3191.507 (2)C117—O11.2261 (19)
C319—H31A0.9700C114—C1131.360 (3)
C319—H31B0.9700C114—H1140.9300
C31—H31C0.9600C120—C1251.374 (2)
C31—H31D0.9600C120—C1211.382 (2)
C31—H31E0.9600C120—C1191.512 (2)
C31—H31F0.9600C111—C1121.374 (3)
C31—H31G0.9600C111—H1110.9300
C31—H31H0.9600C112—C1131.379 (3)
C325—C3241.379 (3)C112—H1120.9300
C325—H3250.9300C125—C1241.385 (3)
C323—C3241.365 (3)C125—H1250.9300
C323—C3221.367 (4)C119—H11A0.9700
C323—H3230.9300C119—H11B0.9700
C321—C3221.374 (3)C113—H1130.9300
C321—H3210.9300C11—H11C0.9600
C322—H3220.9300C11—H11D0.9600
C324—H3240.9300C11—H11E0.9600
C210—C2151.394 (2)C124—C1231.355 (3)
C210—C2111.3983 (19)C124—H1240.9300
C215—C2141.394 (2)C122—C1231.357 (4)
C217—O21.2185 (19)C122—C1211.388 (3)
C217—C2161.478 (2)C122—H1220.9300
C211—C2121.371 (2)C123—H1230.9300
C211—H2110.9300C121—H1210.9300
C216—C211.495 (2)
C117—N11—C110121.79 (13)N21—C219—C220113.86 (14)
C117—N11—C119117.13 (14)N21—C219—H21A108.8
C110—N11—C119121.08 (14)C220—C219—H21A108.8
C116—N12—C115118.81 (13)N21—C219—H21B108.8
C217—N21—C210121.92 (13)C220—C219—H21B108.8
C217—N21—C219117.66 (13)H21A—C219—H21B107.7
C210—N21—C219120.41 (12)C216—C21—H21C109.5
C216—N22—C215118.75 (13)C216—C21—H21D109.5
C317—N31—C310121.23 (12)H21C—C21—H21D109.5
C317—N31—C319118.47 (13)C216—C21—H21E109.5
C310—N31—C319120.27 (13)H21C—C21—H21E109.5
C316—N32—C315118.81 (13)H21D—C21—H21E109.5
N31—C310—C311122.63 (14)C216—C21—H21F109.5
N31—C310—C315118.51 (13)H21C—C21—H21F141.1
C311—C310—C315118.85 (14)H21D—C21—H21F56.3
N32—C316—C317123.92 (13)H21E—C21—H21F56.3
N32—C316—C31119.39 (15)C216—C21—H21G109.5
C317—C316—C31116.69 (14)H21C—C21—H21G56.3
O3—C317—N31122.14 (15)H21D—C21—H21G141.1
O3—C317—C316122.08 (15)H21E—C21—H21G56.3
N31—C317—C316115.77 (13)H21F—C21—H21G109.5
C313—C314—C315120.65 (16)C216—C21—H21H109.5
C313—C314—H314119.7H21C—C21—H21H56.3
C315—C314—H314119.7H21D—C21—H21H56.3
C312—C311—C310119.83 (16)H21E—C21—H21H141.1
C312—C311—H311120.1H21F—C21—H21H109.5
C310—C311—H311120.1H21G—C21—H21H109.5
C314—C313—C312119.32 (15)C225—C220—C221118.69 (18)
C314—C313—H313120.3C225—C220—C219122.86 (16)
C312—C313—H313120.3C221—C220—C219118.43 (19)
C311—C312—C313121.41 (16)C220—C225—C224120.62 (19)
C311—C312—H312119.3C220—C225—H225119.7
C313—C312—H312119.3C224—C225—H225119.7
C325—C320—C321118.56 (17)C223—C224—C225120.2 (2)
C325—C320—C319122.91 (15)C223—C224—H224119.9
C321—C320—C319118.50 (16)C225—C224—H224119.9
N31—C319—C320114.42 (13)C223—C222—C221121.2 (3)
N31—C319—H31A108.7C223—C222—H222119.4
C320—C319—H31A108.7C221—C222—H222119.4
N31—C319—H31B108.7C222—C223—C224119.5 (2)
C320—C319—H31B108.7C222—C223—H223120.3
H31A—C319—H31B107.6C224—C223—H223120.3
C316—C31—H31C109.5C220—C221—C222119.8 (3)
C316—C31—H31D109.5C220—C221—H221120.1
H31C—C31—H31D109.5C222—C221—H221120.1
C316—C31—H31E109.5C110—C115—N12122.21 (13)
H31C—C31—H31E109.5C110—C115—C114119.57 (14)
H31D—C31—H31E109.5N12—C115—C114118.22 (14)
C316—C31—H31F109.5C115—C110—C111119.38 (15)
H31C—C31—H31F141.1C115—C110—N11117.70 (13)
H31D—C31—H31F56.3C111—C110—N11122.91 (14)
H31E—C31—H31F56.3N12—C116—C117123.73 (14)
C316—C31—H31G109.5N12—C116—C11119.35 (16)
H31C—C31—H31G56.3C117—C116—C11116.91 (16)
H31D—C31—H31G141.1O1—C117—N11122.09 (16)
H31E—C31—H31G56.3O1—C117—C116122.16 (17)
H31F—C31—H31G109.5N11—C117—C116115.74 (13)
C316—C31—H31H109.5C113—C114—C115121.00 (17)
H31C—C31—H31H56.3C113—C114—H114119.5
H31D—C31—H31H56.3C115—C114—H114119.5
H31E—C31—H31H141.1C125—C120—C121118.34 (17)
H31F—C31—H31H109.5C125—C120—C119122.77 (14)
H31G—C31—H31H109.5C121—C120—C119118.90 (16)
C320—C325—C324120.63 (19)C112—C111—C110119.25 (17)
C320—C325—H325119.7C112—C111—H111120.4
C324—C325—H325119.7C110—C111—H111120.4
C324—C323—C322119.4 (2)C111—C112—C113121.61 (17)
C324—C323—H323120.3C111—C112—H112119.2
C322—C323—H323120.3C113—C112—H112119.2
C322—C321—C320120.3 (2)C120—C125—C124120.60 (19)
C322—C321—H321119.9C120—C125—H125119.7
C320—C321—H321119.9C124—C125—H125119.7
C323—C322—C321120.7 (2)N11—C119—C120113.91 (14)
C323—C322—H322119.6N11—C119—H11A108.8
C321—C322—H322119.6C120—C119—H11A108.8
C323—C324—C325120.4 (2)N11—C119—H11B108.8
C323—C324—H324119.8C120—C119—H11B108.8
C325—C324—H324119.8H11A—C119—H11B107.7
N21—C210—C215118.06 (12)C114—C113—C112119.15 (17)
N21—C210—C211122.81 (13)C114—C113—H113120.4
C215—C210—C211119.13 (13)C112—C113—H113120.4
N22—C215—C210122.03 (13)C116—C11—H11C109.5
N22—C215—C214118.47 (14)C116—C11—H11D109.5
C210—C215—C214119.49 (14)H11C—C11—H11D109.5
O2—C217—N21122.38 (16)C116—C11—H11E109.5
O2—C217—C216122.44 (15)H11C—C11—H11E109.5
N21—C217—C216115.18 (13)H11D—C11—H11E109.5
C212—C211—C210120.35 (15)C123—C124—C125120.7 (2)
C212—C211—H211119.8C123—C124—H124119.6
C210—C211—H211119.8C125—C124—H124119.6
N22—C216—C217123.92 (13)C123—C122—C121120.9 (2)
N22—C216—C21119.22 (16)C123—C122—H122119.5
C217—C216—C21116.85 (15)C121—C122—H122119.5
C211—C212—C213120.53 (15)C124—C123—C122119.4 (2)
C211—C212—H212119.7C124—C123—H123120.3
C213—C212—H212119.7C122—C123—H123120.3
C213—C214—C215120.48 (16)C120—C121—C122120.0 (2)
C213—C214—H214119.8C120—C121—H121120.0
C215—C214—H214119.8C122—C121—H121120.0
C214—C213—C212120.00 (15)N32—C315—C314118.37 (14)
C214—C213—H213120.0N32—C315—C310121.69 (13)
C212—C213—H213120.0C314—C315—C310119.92 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C119—H11B···O10.972.342.706 (3)102
C219—H21B···O20.972.322.722 (2)104
C21—H21F···O20.962.372.824 (3)109
C319—H31B···O30.972.332.740 (2)105
C31—H31F···O30.962.352.810 (3)109
C125—H125···N110.932.512.858 (2)102
C125—H125···N12i0.932.623.423 (2)145
C225—H225···N210.932.532.864 (3)102
C321—H321···O1ii0.932.563.320 (3)140
C325—H325···N310.932.572.898 (3)101
C325—H325···N32iii0.932.513.380 (3)155

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2301).

References

  • Abasolo, M. I., Gaozza, C. H. & Fernandez, B. M. (1987). J. Heterocycl. Chem.24, 1771–1775.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jampilek, J., Dolezal, M., Kunes, J., Buchta, V. & Kralova, K. (2005). Med. Chem.1, 591–599. [PubMed]
  • Kleim, J. P., Bender, R., Kirsch, R., Meichsner, C., Paessens, A., Rosner, M., Rubsamen Waigmann, H., Kaiser, R., Wichers, M., Schneweis, K. E., Winkler, I. & Riess, G. (1995). Antimicrob. Agents Chemother.39, 2253–2257. [PMC free article] [PubMed]
  • Rodrigo, G. A., Robinshon, A. E., Hedrera, M. E., Kogan, M., Sicardi, S. M. & Fernaandez, B. M. (2002). Trends Heterocycl. Chem.8, 137–143.
  • Sashidhara, K. V., Kumar, A., Bhatia, G., Khan, M. M., Khanna, A. K. & Saxena, J. K. (2009). Eur. J. Med. Chem.44, 1813–1818. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Watkins, A. J., Nicol, G. W. & Shawa, L. J. (2009). Soil Biol. Biochem.41, 580–585.
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920-925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography