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Acta Cryst. (2007). E63, o4104-o4105
https://doi.org/10.1107/S1600536807044492
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4,5-Dimethyl-1,2-bis(pyridine-3-carbox­amido)­benzene

H. Kwak, C.-H. Park, P.-G. Kim, C. Kim and Y. Kim
In the title mol­ecule, C20H18N4O2, the dihedral angles between the central benzene ring and the two pyridine rings are 12.07 (8) and 4.80 (1)°, and that between the two pyridine rings is 16.78 (9)°. An intra­molecular N—H...O hydrogen bond may influence the mol­ecular conformation. In the crystal structure, inter­molecular N—H...O hydrogen bonds link mol­ecules into centrosymmetric dimers, while weak inter­molecuar C—H...O hydrogen bonds link these dimers into one-dimensional chains.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044492/lh2501sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044492/lh2501Isup2.hkl
Contains datablock I

CCDC reference: 663799

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.111
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?


Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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
Comment top

The rational design and construction of novel discrete and polymeric metal–organic complexes has been the subject of enormous studies in recent years, not only due to their structural and topological novelty (Batten & Robson, 1998; Moler et al., 2001; Moulton & Zaworotko, 2001), but also for their potential applications as functional materials in areas such as catalysis, molecular recognition, separation, and nonlinear optics (Hong et al., 2004; Evans & Lin, 2002; Kasai et al., 2000; Kitagawa et al., 2004). The structure of metal–organic complexes is highly influenced by many factors such as the coordination geometry of metal ions (Chi et al., 2006), the structure of organic ligands (Wang et al., 2006), the solvent system (Ryu et al., 2005), the counteranion (Luan et al., 2006), and the ratio of ligands to metal ions. In addition, the secondary forces such as hydrogen-bonding, pi–pi stacking, and host–guest interactions must be considered as well (Luan et al., 2005; Janiak & Scharmann, 2003; Janiak, 2003). For obtaining novel structural motifs with predictable properties, a large number of organic ligands have been designed and utilized. Recently, much attention was paid to ligands with amide moieties that can assemble into higher dimensional architectures via hydrogen-bonded interactions (Sarkar & Biradha, 2007). In order to further investigate the influence of the ligand with amide moieties on the crystal structure, we synthesized the title compound an we report its crystal structure herein.

The asymmetric unit of the monoclinic unit cell contains one whole molecule [P21/c and Z = 4]. The molecule is not planar, having twisted angles between the central benzene ring and two pyridyl rings. The dihedral angles between the central benzene ring and the two pyridyl rings are 12.07 (8)° and 4.80 (1)° (Fig. 1). An intramolecular N—H···O hydrogen bond may influence the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into centrosymmetric dimers while weak intermolecuar C—H···O hydrogen bonds link these dimers into one-dimensional chains (Fig. 2).

Related literature top

The molecule of the corresponding H2Me2-bpzb compound [bpzb is 1,2-bis(2-pyrazine-3-carboxamido)-4,5-dimethylbenzene] is non-planar (Kim et al., 2005). For background information, see: Batten & Robson (1998); Chi et al. (2006); Evans & Lin (2002); Hong et al. (2004); Janiak (2003); Janiak & Scharmann (2003); Kasai et al. (2000); Kitagawa et al. (2004); Luan et al. (2005, 2006); Moler et al. (2001); Moulton & Zaworotko (2001); Ryu et al. (2005); Sarkar & Biradha (2007); Wang et al. (2006).

Experimental top

4,5-Dimethyl-1,2-phenylenediamine (1.39 g, 10.0 mmol) and triethylamine (4.2 ml, 30.0 mmol) were dissolved in pyridine and stirred for 10 min. Nicotinoyl chloride (3.67 g, 20.0 mmol) dissolved in pyridine was added slowly to the resulting solution at 272 K. After the reaction mixture was stirred for 4 h at room temperature, solvent was removed with a evaporator. The product was dissolved in chloroform and extracted with brine and water. The extracted solution was dried over anhydrous Na2SO4. The powered product was obtained in a mixture of ether and chloroform (4:1). Colorless block crystals were obtained from an acetone–hexane solution at room temperature by slow evaporation for X-ray experiments.

Refinement top

H atoms were placed in calculated positions with C—H distances of 0.93 A% (benzene and pyridine) and 0.96 A% (methyl). They were included in the refinement in riding–motion approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C). The H atoms bonded to N atoms were refined independently with isotropic displacement parameters.

Structure description top

The rational design and construction of novel discrete and polymeric metal–organic complexes has been the subject of enormous studies in recent years, not only due to their structural and topological novelty (Batten & Robson, 1998; Moler et al., 2001; Moulton & Zaworotko, 2001), but also for their potential applications as functional materials in areas such as catalysis, molecular recognition, separation, and nonlinear optics (Hong et al., 2004; Evans & Lin, 2002; Kasai et al., 2000; Kitagawa et al., 2004). The structure of metal–organic complexes is highly influenced by many factors such as the coordination geometry of metal ions (Chi et al., 2006), the structure of organic ligands (Wang et al., 2006), the solvent system (Ryu et al., 2005), the counteranion (Luan et al., 2006), and the ratio of ligands to metal ions. In addition, the secondary forces such as hydrogen-bonding, pi–pi stacking, and host–guest interactions must be considered as well (Luan et al., 2005; Janiak & Scharmann, 2003; Janiak, 2003). For obtaining novel structural motifs with predictable properties, a large number of organic ligands have been designed and utilized. Recently, much attention was paid to ligands with amide moieties that can assemble into higher dimensional architectures via hydrogen-bonded interactions (Sarkar & Biradha, 2007). In order to further investigate the influence of the ligand with amide moieties on the crystal structure, we synthesized the title compound an we report its crystal structure herein.

The asymmetric unit of the monoclinic unit cell contains one whole molecule [P21/c and Z = 4]. The molecule is not planar, having twisted angles between the central benzene ring and two pyridyl rings. The dihedral angles between the central benzene ring and the two pyridyl rings are 12.07 (8)° and 4.80 (1)° (Fig. 1). An intramolecular N—H···O hydrogen bond may influence the molecular conformation. In the crystal structure, intermolecular N—H···O hydrogen bonds link molecules into centrosymmetric dimers while weak intermolecuar C—H···O hydrogen bonds link these dimers into one-dimensional chains (Fig. 2).

The molecule of the corresponding H2Me2-bpzb compound [bpzb is 1,2-bis(2-pyrazine-3-carboxamido)-4,5-dimethylbenzene] is non-planar (Kim et al., 2005). For background information, see: Batten & Robson (1998); Chi et al. (2006); Evans & Lin (2002); Hong et al. (2004); Janiak (2003); Janiak & Scharmann (2003); Kasai et al. (2000); Kitagawa et al. (2004); Luan et al. (2005, 2006); Moler et al. (2001); Moulton & Zaworotko (2001); Ryu et al. (2005); Sarkar & Biradha (2007); Wang et al. (2006).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Part of the crystal structure showing hydrogen bonds as dashed lines.
4,5-Dimethyl-1,2-bis(pyridine-3-carboxamido)benzene top
Crystal data top
C20H18N4O2F(000) = 728
Mr = 346.38Dx = 1.332 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1519 reflections
a = 8.086 (2) Åθ = 2.3–21.6°
b = 17.960 (5) ŵ = 0.09 mm−1
c = 12.135 (3) ÅT = 293 K
β = 101.467 (5)°Block, colourless
V = 1727.2 (8) Å30.25 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3391 independent reflections
Radiation source: fine-focus sealed tube2300 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −9→9
Tmin = 0.978, Tmax = 0.982k = −22→22
9503 measured reflectionsl = −8→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2189P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3391 reflectionsΔρmax = 0.18 e Å−3
246 parametersΔρmin = −0.16 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0233 (19)
Crystal data top
C20H18N4O2V = 1727.2 (8) Å3
Mr = 346.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.086 (2) ŵ = 0.09 mm−1
b = 17.960 (5) ÅT = 293 K
c = 12.135 (3) Å0.25 × 0.25 × 0.20 mm
β = 101.467 (5)°
Data collection top
Bruker SMART CCD
diffractometer		3391 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		2300 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.982Rint = 0.030
9503 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å−3
3391 reflectionsΔρmin = −0.16 e Å−3
246 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
N10.5376 (2)0.74635 (9)0.34859 (15)0.0654 (5)
N20.28726 (18)0.52612 (8)0.46355 (13)0.0414 (4)
H2N0.356 (2)0.5308 (10)0.5311 (17)0.054 (5)*
N30.16193 (17)0.45162 (7)0.64598 (11)0.0395 (3)
H3N0.069 (2)0.4465 (9)0.6770 (14)0.048 (5)*
N40.1892 (2)0.45996 (12)0.99772 (15)0.0791 (6)
O10.16797 (14)0.58349 (6)0.29969 (9)0.0481 (3)
O20.42842 (14)0.49969 (7)0.68104 (10)0.0513 (3)
C10.4360 (2)0.68713 (10)0.33456 (16)0.0535 (5)
H10.39270.67190.26120.064*
C20.5950 (3)0.76727 (11)0.45490 (19)0.0619 (5)
H20.66520.80870.46760.074*
C30.5569 (2)0.73150 (10)0.54635 (17)0.0566 (5)
H30.60010.74860.61870.068*
C40.4536 (2)0.66975 (9)0.52960 (16)0.0496 (5)
H40.42720.64420.59050.060*
C50.3900 (2)0.64649 (9)0.42080 (14)0.0408 (4)
C60.2720 (2)0.58253 (9)0.38911 (14)0.0402 (4)
C70.19937 (19)0.45736 (9)0.44661 (14)0.0381 (4)
C80.1681 (2)0.42332 (9)0.34149 (14)0.0458 (4)
H80.20850.44580.28300.055*
C90.0792 (2)0.35732 (10)0.32058 (14)0.0468 (4)
C100.0223 (2)0.32184 (9)0.40926 (15)0.0452 (4)
C110.0582 (2)0.35489 (9)0.51430 (14)0.0424 (4)
H110.02270.33120.57370.051*
C120.14512 (19)0.42190 (8)0.53512 (13)0.0363 (4)
C130.2963 (2)0.48389 (9)0.71203 (14)0.0391 (4)
C140.2776 (2)0.49965 (9)0.82949 (14)0.0403 (4)
C150.3483 (2)0.56311 (10)0.88388 (16)0.0549 (5)
H150.40490.59700.84680.066*
C160.3339 (3)0.57546 (12)0.99318 (17)0.0670 (6)
H160.37760.61851.03060.080*
C170.2542 (3)0.52323 (14)1.04615 (19)0.0740 (6)
H170.24470.53221.12010.089*
C180.1988 (2)0.45048 (11)0.89029 (16)0.0588 (5)
H180.14950.40810.85380.071*
C190.0500 (3)0.32368 (11)0.20413 (17)0.0689 (6)
H19A0.07370.36020.15160.103*
H19B−0.06540.30790.18270.103*
H19C0.12310.28160.20410.103*
C20−0.0709 (3)0.24884 (10)0.39309 (19)0.0696 (6)
H20A−0.09070.23150.46420.104*
H20B−0.00450.21280.36270.104*
H20C−0.17690.25560.34210.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0692 (11)0.0592 (10)0.0661 (12)−0.0163 (9)0.0091 (9)0.0101 (9)
N20.0444 (8)0.0462 (8)0.0336 (8)−0.0022 (7)0.0081 (7)0.0015 (7)
N30.0380 (8)0.0476 (8)0.0345 (8)−0.0027 (6)0.0110 (6)−0.0021 (6)
N40.0844 (13)0.1113 (15)0.0429 (11)−0.0207 (12)0.0157 (9)0.0045 (11)
O10.0473 (7)0.0567 (7)0.0388 (7)−0.0034 (6)0.0049 (6)0.0052 (6)
O20.0395 (7)0.0726 (8)0.0426 (7)−0.0055 (6)0.0098 (5)−0.0003 (6)
C10.0585 (11)0.0526 (10)0.0480 (11)−0.0062 (9)0.0070 (9)0.0062 (9)
C20.0574 (12)0.0503 (11)0.0749 (15)−0.0081 (9)0.0058 (11)0.0001 (11)
C30.0560 (12)0.0520 (11)0.0584 (13)0.0014 (9)0.0033 (10)−0.0086 (10)
C40.0533 (11)0.0491 (10)0.0467 (11)0.0029 (9)0.0105 (9)0.0017 (8)
C50.0391 (9)0.0417 (9)0.0420 (10)0.0035 (7)0.0087 (7)0.0033 (8)
C60.0398 (9)0.0474 (9)0.0356 (10)0.0023 (8)0.0126 (7)0.0008 (8)
C70.0372 (9)0.0411 (9)0.0371 (9)0.0035 (7)0.0099 (7)−0.0004 (7)
C80.0521 (10)0.0506 (10)0.0366 (10)0.0051 (8)0.0138 (8)−0.0009 (8)
C90.0502 (10)0.0488 (10)0.0403 (10)0.0076 (9)0.0063 (8)−0.0086 (8)
C100.0454 (10)0.0402 (9)0.0491 (11)0.0042 (8)0.0071 (8)−0.0063 (8)
C110.0459 (10)0.0396 (9)0.0423 (10)0.0006 (8)0.0105 (8)0.0009 (8)
C120.0363 (9)0.0397 (9)0.0330 (9)0.0043 (7)0.0071 (7)−0.0014 (7)
C130.0387 (9)0.0409 (9)0.0374 (10)0.0019 (7)0.0065 (7)0.0020 (7)
C140.0395 (9)0.0472 (9)0.0335 (9)0.0018 (7)0.0054 (7)0.0020 (8)
C150.0683 (13)0.0517 (11)0.0449 (11)−0.0074 (9)0.0119 (9)−0.0019 (9)
C160.0866 (16)0.0660 (13)0.0464 (12)0.0005 (11)0.0087 (11)−0.0159 (10)
C170.0796 (15)0.1054 (18)0.0397 (12)0.0062 (14)0.0183 (11)−0.0067 (13)
C180.0662 (13)0.0698 (12)0.0400 (11)−0.0193 (10)0.0097 (9)0.0008 (10)
C190.0869 (15)0.0688 (13)0.0510 (12)0.0008 (11)0.0137 (11)−0.0189 (11)
C200.0813 (15)0.0554 (12)0.0711 (15)−0.0131 (11)0.0128 (12)−0.0160 (11)
Geometric parameters (Å, º) top
N1—C11.334 (2)C8—C91.383 (2)
N1—C21.335 (3)C8—H80.9300
N2—C61.347 (2)C9—C101.404 (2)
N2—C71.419 (2)C9—C191.512 (2)
N2—H2N0.90 (2)C10—C111.384 (2)
N3—C131.346 (2)C10—C201.506 (2)
N3—C121.428 (2)C11—C121.391 (2)
N3—H3N0.907 (17)C11—H110.9300
N4—C181.332 (2)C13—C141.490 (2)
N4—C171.338 (3)C14—C151.382 (2)
O1—C61.2340 (19)C14—C181.384 (2)
O2—C131.2345 (19)C15—C161.372 (3)
C1—C51.386 (2)C15—H150.9300
C1—H10.9300C16—C171.369 (3)
C2—C31.369 (3)C16—H160.9300
C2—H20.9300C17—H170.9300
C3—C41.379 (2)C18—H180.9300
C3—H30.9300C19—H19A0.9600
C4—C51.383 (2)C19—H19B0.9600
C4—H40.9300C19—H19C0.9600
C5—C61.494 (2)C20—H20A0.9600
C7—C81.392 (2)C20—H20B0.9600
C7—C121.392 (2)C20—H20C0.9600
C1—N1—C2115.76 (17)C9—C10—C20121.80 (16)
C6—N2—C7125.53 (15)C10—C11—C12122.98 (15)
C6—N2—H2N120.0 (12)C10—C11—H11118.5
C7—N2—H2N114.5 (12)C12—C11—H11118.5
C13—N3—C12129.50 (14)C11—C12—C7118.73 (15)
C13—N3—H3N115.5 (11)C11—C12—N3116.38 (14)
C12—N3—H3N114.9 (11)C7—C12—N3124.75 (14)
C18—N4—C17116.35 (19)O2—C13—N3124.23 (15)
N1—C1—C5125.06 (18)O2—C13—C14120.41 (15)
N1—C1—H1117.5N3—C13—C14115.36 (14)
C5—C1—H1117.5C15—C14—C18117.49 (16)
N1—C2—C3124.06 (18)C15—C14—C13120.17 (15)
N1—C2—H2118.0C18—C14—C13122.24 (16)
C3—C2—H2118.0C16—C15—C14119.24 (18)
C2—C3—C4119.02 (18)C16—C15—H15120.4
C2—C3—H3120.5C14—C15—H15120.4
C4—C3—H3120.5C17—C16—C15118.8 (2)
C3—C4—C5118.88 (17)C17—C16—H16120.6
C3—C4—H4120.6C15—C16—H16120.6
C5—C4—H4120.6N4—C17—C16123.8 (2)
C4—C5—C1117.21 (16)N4—C17—H17118.1
C4—C5—C6125.11 (15)C16—C17—H17118.1
C1—C5—C6117.65 (15)N4—C18—C14124.24 (19)
O1—C6—N2123.77 (15)N4—C18—H18117.9
O1—C6—C5120.29 (15)C14—C18—H18117.9
N2—C6—C5115.94 (15)C9—C19—H19A109.5
C8—C7—C12118.58 (15)C9—C19—H19B109.5
C8—C7—N2120.63 (15)H19A—C19—H19B109.5
C12—C7—N2120.78 (14)C9—C19—H19C109.5
C9—C8—C7122.53 (16)H19A—C19—H19C109.5
C9—C8—H8118.7H19B—C19—H19C109.5
C7—C8—H8118.7C10—C20—H20A109.5
C8—C9—C10119.05 (15)C10—C20—H20B109.5
C8—C9—C19119.53 (16)H20A—C20—H20B109.5
C10—C9—C19121.40 (17)C10—C20—H20C109.5
C11—C10—C9118.08 (15)H20A—C20—H20C109.5
C11—C10—C20120.10 (16)H20B—C20—H20C109.5
C2—N1—C1—C5−1.1 (3)C9—C10—C11—C121.1 (2)
C1—N1—C2—C30.7 (3)C20—C10—C11—C12179.44 (16)
N1—C2—C3—C40.3 (3)C10—C11—C12—C7−0.3 (2)
C2—C3—C4—C5−0.8 (3)C10—C11—C12—N3175.65 (14)
C3—C4—C5—C10.4 (2)C8—C7—C12—C11−1.6 (2)
C3—C4—C5—C6−177.68 (15)N2—C7—C12—C11179.49 (14)
N1—C1—C5—C40.6 (3)C8—C7—C12—N3−177.19 (14)
N1—C1—C5—C6178.84 (17)N2—C7—C12—N33.9 (2)
C7—N2—C6—O16.3 (3)C13—N3—C12—C11138.35 (17)
C7—N2—C6—C5−174.10 (13)C13—N3—C12—C7−45.9 (2)
C4—C5—C6—O1148.83 (17)C12—N3—C13—O27.3 (3)
C1—C5—C6—O1−29.3 (2)C12—N3—C13—C14−172.16 (14)
C4—C5—C6—N2−30.8 (2)O2—C13—C14—C1536.5 (2)
C1—C5—C6—N2151.08 (16)N3—C13—C14—C15−144.00 (16)
C6—N2—C7—C837.4 (2)O2—C13—C14—C18−139.76 (18)
C6—N2—C7—C12−143.67 (16)N3—C13—C14—C1839.7 (2)
C12—C7—C8—C92.8 (2)C18—C14—C15—C16−1.6 (3)
N2—C7—C8—C9−178.30 (15)C13—C14—C15—C16−178.07 (17)
C7—C8—C9—C10−2.0 (3)C14—C15—C16—C171.9 (3)
C7—C8—C9—C19179.94 (16)C18—N4—C17—C16−2.8 (3)
C8—C9—C10—C110.0 (2)C15—C16—C17—N40.3 (3)
C19—C9—C10—C11178.07 (17)C17—N4—C18—C143.1 (3)
C8—C9—C10—C20−178.29 (17)C15—C14—C18—N4−1.0 (3)
C19—C9—C10—C20−0.2 (3)C13—C14—C18—N4175.37 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O10.932.512.921 (2)107
N2—H2N···O20.90 (2)1.88 (2)2.701 (2)150.8 (16)
C17—H17···O1i0.932.553.461 (3)165
N3—H3N···O1ii0.907 (17)2.066 (18)2.9407 (19)161.6 (15)
Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC20H18N4O2
Mr346.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.086 (2), 17.960 (5), 12.135 (3)
β (°) 101.467 (5)
V (Å3)1727.2 (8)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.25 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.978, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections		9503, 3391, 2300
Rint0.030
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.111, 1.04
No. of reflections3391
No. of parameters246
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.18, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O10.932.512.921 (2)107.2
N2—H2N···O20.90 (2)1.88 (2)2.701 (2)150.8 (16)
C17—H17···O1i0.932.553.461 (3)165.3
N3—H3N···O1ii0.907 (17)2.066 (18)2.9407 (19)161.6 (15)
Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1, −z+1.
 

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