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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2825
https://doi.org/10.1107/S1600536810040468

(E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyl­imino­meth­yl)phenol

Chi-Huan Li,a Jing-Kai Su,a Chen-Yu Lia and Bao-Tsan Koa*

aDepartment of Chemistry, Chung Yuan Christian University, Chung-Li 32023, Taiwan
*Correspondence e-mail: btko@cycu.edu.tw

(Received 4 October 2010; accepted 9 October 2010; online 20 October 2010)

In the title compound, C20H16N4O, the non-H atoms of the benzotriazole ring system and those of the methyl­phenol group are essentially coplanar, with an r.m.s. deviation of 0.004 (2) Å. The mean plane of these atoms forms a dihedral angle of 60.9 (2)° with the phenyl ring. There is an intra­molecular O—H⋯N hydrogen bond between the phenol and benzotriazole groups.

Related literature

For related structures, see: Chen et al. (2010[Chen, M.-J., Li, C.-Y., Tsai, C.-Y. & Ko, B.-T. (2010). Acta Cryst. E66, o2279.]); Li et al. (2009[Li, J.-Y., Liu, Y.-C., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, o2475.], 2010[Li, C.-Y., Tsai, C.-Y., Lin, C.-H. & Ko, B.-T. (2010). Acta Cryst. E66, o726.]).

[Scheme 1]

Experimental

Crystal data

  • C20H16N4O

  • Mr = 328.37

  • Monoclinic, P 21 /c

  • a = 15.7279 (5) Å

  • b = 12.3002 (4) Å

  • c = 8.4903 (3) Å

  • β = 104.842 (1)°

  • V = 1587.70 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 173 K

  • 0.48 × 0.37 × 0.21 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.982

  • 15472 measured reflections

  • 3924 independent reflections

  • 2874 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.143

  • S = 1.01

  • 3924 reflections

  • 228 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O—H0A⋯N1 0.84 1.85 2.591 (2) 146

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810040468/lh5146sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040468/lh5146Isup2.hkl

checkCIF report


Comment top

Recently, benzotriazole-phenol (BTP-H) derivatives have attracted our attention because the benzotriazole-phenolate group can provide the N,O-bidentate chelation to stabilize the transition metal or main group metal complexes. Therefore, our group is interested in the design and synthesis of functionalized benzotriazole-phenolate ligands derived from 4-methyl-2-(2H-benzotriazol-2-yl)phenol (MeBTP-H). For instance, our group has successfully synthesized and structural characterized the methyl ether functionalized BTP derivative via etherification derived from MeBTP-H (Chen et al., 2010). We have also reported the synthesis and crystal structure of a salicylaldehyde group substituted benzotriazole derivative (Li et al., 2010). As part of our goal to prepare NNO-tridentate Schiff-base ligands originating from BTP derivatives, we report herein the synthesis and crystal structure of the title compound, (I), which is a potential ligand for the preparation of NNO-tridentate Schiff-base zinc (Zn) and magnesium (Mg) complexes.

The molecular structure of (I) shows a 4-methyl-2-((phenylimino)methyl)phenol moiety with a benzotriazole functionalized group on the 6-position (Fig. 1). The non-hydrogen atoms of the benzotriazole ring system and those of the methylphenol group are essentially co-planar with an r.m.s. deviation of 0.004 (2) Å. The mean-plane of these atoms forms a dihedral angle of 60.9 (2)° with the phenyl ring. There is an intramolecular O—H···N hydrogen bond between the phenol and benzotriazole groups (see Table 1). The bond distances of the benzotriazole-phenolate group are similar to those found in the crystal structure of 2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol (Li et al., 2009).

Related literature top

For related structures, see: Chen et al. (2010); Li et al. (2009, 2010).

Experimental top

The title compound (I) was synthesized by the following procedure: (Fig. 2): A mixture of aniline (0.27 ml, 3.0 mmol), 3-(2H-benzotriazol-2-yl)-2-hydroxy-5-methylbenzaldehyde (0.68 g, 2.7 mmol) and anhydrous MgSO4 (2.0 g) were stirred in reflux toluene (20 ml) for 12 h. Volatile materials were removed under vacuum to give yellow solids. Yield: 0.71 g (80%). Yellow crystals were obtained from a saturated Et2O solution.

Refinement top

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C–H = 0.95 Å with Uiso(H) = 1.2 Ueq(C) for phenyl hydrogen; 0.98 Å with Uiso(H) = 1.5 Ueq(C) for CH3 group; 0.95 Å with Uiso(H) = 1.2 Ueq(C) for HC=N group; O–H = 0.84 Å with Uiso(H) = 1.5 Ueq(O).

Structure description top

Recently, benzotriazole-phenol (BTP-H) derivatives have attracted our attention because the benzotriazole-phenolate group can provide the N,O-bidentate chelation to stabilize the transition metal or main group metal complexes. Therefore, our group is interested in the design and synthesis of functionalized benzotriazole-phenolate ligands derived from 4-methyl-2-(2H-benzotriazol-2-yl)phenol (MeBTP-H). For instance, our group has successfully synthesized and structural characterized the methyl ether functionalized BTP derivative via etherification derived from MeBTP-H (Chen et al., 2010). We have also reported the synthesis and crystal structure of a salicylaldehyde group substituted benzotriazole derivative (Li et al., 2010). As part of our goal to prepare NNO-tridentate Schiff-base ligands originating from BTP derivatives, we report herein the synthesis and crystal structure of the title compound, (I), which is a potential ligand for the preparation of NNO-tridentate Schiff-base zinc (Zn) and magnesium (Mg) complexes.

The molecular structure of (I) shows a 4-methyl-2-((phenylimino)methyl)phenol moiety with a benzotriazole functionalized group on the 6-position (Fig. 1). The non-hydrogen atoms of the benzotriazole ring system and those of the methylphenol group are essentially co-planar with an r.m.s. deviation of 0.004 (2) Å. The mean-plane of these atoms forms a dihedral angle of 60.9 (2)° with the phenyl ring. There is an intramolecular O—H···N hydrogen bond between the phenol and benzotriazole groups (see Table 1). The bond distances of the benzotriazole-phenolate group are similar to those found in the crystal structure of 2-(2H-benzotriazol-2-yl)-6-((diethylamino)methyl)-4-methylphenol (Li et al., 2009).

For related structures, see: Chen et al. (2010); Li et al. (2009, 2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 60% probability level.
[Figure 2] Fig. 2. The synthetic procedure of in the preparation of I.
(E)-2-(2H-Benzotriazol-2-yl)-4-methyl-6-(phenyliminomethyl)phenol top
Crystal data top
C20H16N4OF(000) = 688
Mr = 328.37Dx = 1.374 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5818 reflections
a = 15.7279 (5) Åθ = 2.7–28.2°
b = 12.3002 (4) ŵ = 0.09 mm−1
c = 8.4903 (3) ÅT = 173 K
β = 104.842 (1)°Block, yellow
V = 1587.70 (9) Å30.48 × 0.37 × 0.21 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		3924 independent reflections
Radiation source: fine-focus sealed tube2874 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.3333 pixels mm-1θmax = 28.3°, θmin = 2.1°
φ and ω scansh = −20→20
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		k = −16→16
Tmin = 0.959, Tmax = 0.982l = −11→10
15472 measured reflections
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0585P)2 + 1.1196P]
where P = (Fo2 + 2Fc2)/3
3924 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C20H16N4OV = 1587.70 (9) Å3
Mr = 328.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.7279 (5) ŵ = 0.09 mm−1
b = 12.3002 (4) ÅT = 173 K
c = 8.4903 (3) Å0.48 × 0.37 × 0.21 mm
β = 104.842 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		3924 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2874 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.982Rint = 0.033
15472 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.143H-atom parameters constrained
S = 1.01Δρmax = 0.41 e Å−3
3924 reflectionsΔρmin = −0.22 e Å−3
228 parameters
Special details top

Experimental. 1H NMR (CDCl3, ppm): δ 8.77 (s, 1H, PhN=CH), 7.31-8.03 (m, 11H, PhH), 2.45 (s, 3H, PhCH3).

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
O0.33970 (8)0.05791 (10)0.32102 (16)0.0282 (3)
H0A0.38390.07490.39600.042*
N10.44430 (10)0.18656 (12)0.52339 (19)0.0261 (3)
N20.39775 (10)0.27027 (12)0.44505 (18)0.0237 (3)
N30.42414 (10)0.36903 (12)0.50100 (19)0.0260 (3)
N40.12957 (11)0.00970 (13)−0.0541 (2)0.0300 (4)
C10.29886 (11)0.14915 (14)0.2511 (2)0.0236 (4)
C20.32445 (11)0.25450 (14)0.3077 (2)0.0236 (4)
C30.27847 (12)0.34491 (14)0.2315 (2)0.0255 (4)
H3B0.29690.41550.27130.031*
C40.20630 (12)0.33396 (14)0.0987 (2)0.0262 (4)
C50.18144 (12)0.22937 (15)0.0425 (2)0.0263 (4)
H5A0.13220.2204−0.04860.032*
C60.22639 (12)0.13762 (14)0.1156 (2)0.0250 (4)
C70.50721 (11)0.23467 (15)0.6408 (2)0.0246 (4)
C80.57746 (12)0.18910 (16)0.7620 (2)0.0297 (4)
H8A0.58660.11280.77200.036*
C90.63115 (12)0.26085 (17)0.8633 (2)0.0313 (4)
H9A0.67890.23350.94630.038*
C100.61819 (12)0.37458 (16)0.8491 (2)0.0317 (4)
H10A0.65750.42090.92300.038*
C110.55176 (13)0.41972 (16)0.7340 (2)0.0300 (4)
H11A0.54400.49630.72560.036*
C120.49490 (12)0.34845 (15)0.6274 (2)0.0250 (4)
C130.15659 (13)0.43184 (15)0.0165 (2)0.0324 (4)
H13A0.14040.47800.09830.049*
H13B0.10330.4080−0.06360.049*
H13C0.19380.4732−0.03850.049*
C140.20102 (12)0.02858 (15)0.0498 (2)0.0266 (4)
H14A0.2401−0.03020.08720.032*
C150.11424 (13)−0.09878 (15)−0.1139 (2)0.0289 (4)
C160.17777 (13)−0.15712 (16)−0.1667 (2)0.0326 (4)
H16A0.2324−0.1241−0.16640.039*
C170.16105 (14)−0.26315 (17)−0.2193 (3)0.0372 (5)
H17A0.2043−0.3025−0.25610.045*
C180.08242 (14)−0.31249 (17)−0.2191 (3)0.0372 (5)
H18A0.0722−0.3862−0.25200.045*
C190.01889 (14)−0.25433 (17)−0.1710 (3)0.0362 (5)
H19A−0.0356−0.2880−0.17200.043*
C200.03324 (13)−0.14724 (17)−0.1210 (2)0.0339 (4)
H20A−0.0119−0.1070−0.09170.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0304 (7)0.0216 (6)0.0312 (7)0.0013 (5)0.0055 (6)0.0000 (5)
N10.0262 (7)0.0248 (8)0.0290 (8)0.0020 (6)0.0101 (6)−0.0001 (6)
N20.0269 (7)0.0220 (7)0.0255 (8)−0.0012 (6)0.0126 (6)−0.0005 (6)
N30.0296 (8)0.0222 (7)0.0279 (8)−0.0019 (6)0.0104 (6)−0.0011 (6)
N40.0343 (8)0.0260 (8)0.0299 (9)0.0017 (7)0.0084 (7)−0.0004 (7)
C10.0263 (8)0.0217 (8)0.0272 (9)0.0018 (7)0.0149 (7)0.0012 (7)
C20.0241 (8)0.0243 (9)0.0256 (9)0.0001 (7)0.0123 (7)0.0005 (7)
C30.0297 (9)0.0207 (8)0.0300 (10)−0.0001 (7)0.0149 (8)−0.0006 (7)
C40.0299 (9)0.0235 (9)0.0296 (10)0.0045 (7)0.0158 (8)0.0031 (7)
C50.0267 (8)0.0276 (9)0.0266 (9)0.0006 (7)0.0105 (7)0.0003 (7)
C60.0282 (9)0.0230 (9)0.0286 (9)−0.0001 (7)0.0157 (8)−0.0002 (7)
C70.0257 (8)0.0254 (9)0.0266 (9)−0.0022 (7)0.0138 (7)−0.0032 (7)
C80.0328 (9)0.0253 (9)0.0338 (10)0.0040 (8)0.0136 (8)0.0013 (8)
C90.0261 (9)0.0394 (11)0.0289 (10)0.0031 (8)0.0080 (8)0.0023 (8)
C100.0308 (9)0.0351 (10)0.0316 (10)−0.0087 (8)0.0123 (8)−0.0055 (8)
C110.0344 (10)0.0253 (9)0.0336 (10)−0.0037 (8)0.0144 (8)−0.0017 (8)
C120.0267 (8)0.0260 (9)0.0261 (9)0.0008 (7)0.0138 (7)0.0026 (7)
C130.0345 (10)0.0262 (9)0.0356 (11)0.0042 (8)0.0070 (8)0.0029 (8)
C140.0301 (9)0.0231 (9)0.0288 (10)0.0014 (7)0.0115 (8)0.0003 (7)
C150.0354 (10)0.0258 (9)0.0231 (9)0.0009 (8)0.0032 (8)0.0013 (7)
C160.0301 (9)0.0352 (10)0.0317 (10)−0.0023 (8)0.0064 (8)−0.0003 (9)
C170.0395 (11)0.0364 (11)0.0363 (11)0.0050 (9)0.0108 (9)−0.0071 (9)
C180.0468 (12)0.0299 (10)0.0323 (11)−0.0038 (9)0.0055 (9)−0.0045 (9)
C190.0354 (10)0.0382 (11)0.0335 (11)−0.0092 (9)0.0059 (9)−0.0025 (9)
C200.0303 (10)0.0380 (11)0.0332 (10)0.0018 (8)0.0076 (8)−0.0027 (9)
Geometric parameters (Å, º) top
O—C11.352 (2)C8—H8A0.9500
O—H0A0.8400C9—C101.414 (3)
N1—N21.338 (2)C9—H9A0.9500
N1—C71.348 (2)C10—C111.354 (3)
N2—N31.331 (2)C10—H10A0.9500
N2—C21.427 (2)C11—C121.404 (3)
N3—C121.358 (2)C11—H11A0.9500
N4—C141.260 (2)C13—H13A0.9800
N4—C151.426 (2)C13—H13B0.9800
C1—C61.404 (3)C13—H13C0.9800
C1—C21.405 (2)C14—H14A0.9500
C2—C31.392 (2)C15—C201.394 (3)
C3—C41.386 (3)C15—C161.394 (3)
C3—H3B0.9500C16—C171.382 (3)
C4—C51.393 (2)C16—H16A0.9500
C4—C131.506 (2)C17—C181.378 (3)
C5—C61.391 (2)C17—H17A0.9500
C5—H5A0.9500C18—C191.373 (3)
C6—C141.468 (2)C18—H18A0.9500
C7—C121.413 (3)C19—C201.385 (3)
C7—C81.418 (3)C19—H19A0.9500
C8—C91.364 (3)C20—H20A0.9500
C1—O—H0A109.5C11—C10—H10A118.8
N2—N1—C7103.56 (15)C9—C10—H10A118.8
N3—N2—N1116.36 (14)C10—C11—C12117.10 (18)
N3—N2—C2121.88 (14)C10—C11—H11A121.4
N1—N2—C2121.76 (14)C12—C11—H11A121.4
N2—N3—C12103.27 (14)N3—C12—C11130.60 (17)
C14—N4—C15117.45 (16)N3—C12—C7108.41 (16)
O—C1—C6118.06 (16)C11—C12—C7120.98 (18)
O—C1—C2123.58 (16)C4—C13—H13A109.5
C6—C1—C2118.35 (16)C4—C13—H13B109.5
C3—C2—C1120.56 (17)H13A—C13—H13B109.5
C3—C2—N2119.07 (16)C4—C13—H13C109.5
C1—C2—N2120.37 (15)H13A—C13—H13C109.5
C4—C3—C2121.34 (17)H13B—C13—H13C109.5
C4—C3—H3B119.3N4—C14—C6122.78 (17)
C2—C3—H3B119.3N4—C14—H14A118.6
C3—C4—C5117.88 (16)C6—C14—H14A118.6
C3—C4—C13121.25 (17)C20—C15—C16119.25 (18)
C5—C4—C13120.86 (17)C20—C15—N4118.99 (17)
C6—C5—C4122.06 (17)C16—C15—N4121.76 (17)
C6—C5—H5A119.0C17—C16—C15119.81 (19)
C4—C5—H5A119.0C17—C16—H16A120.1
C5—C6—C1119.80 (16)C15—C16—H16A120.1
C5—C6—C14120.93 (17)C18—C17—C16120.77 (19)
C1—C6—C14119.24 (16)C18—C17—H17A119.6
N1—C7—C12108.40 (16)C16—C17—H17A119.6
N1—C7—C8130.60 (17)C19—C18—C17119.52 (19)
C12—C7—C8121.00 (17)C19—C18—H18A120.2
C9—C8—C7116.32 (18)C17—C18—H18A120.2
C9—C8—H8A121.8C18—C19—C20120.85 (19)
C7—C8—H8A121.8C18—C19—H19A119.6
C8—C9—C10122.26 (19)C20—C19—H19A119.6
C8—C9—H9A118.9C19—C20—C15119.70 (19)
C10—C9—H9A118.9C19—C20—H20A120.1
C11—C10—C9122.34 (19)C15—C20—H20A120.1
C7—N1—N2—N3−0.34 (18)N1—C7—C8—C9179.37 (18)
C7—N1—N2—C2178.92 (14)C12—C7—C8—C90.3 (2)
N1—N2—N3—C120.31 (18)C7—C8—C9—C10−0.2 (3)
C2—N2—N3—C12−178.95 (14)C8—C9—C10—C11−0.1 (3)
O—C1—C2—C3−178.92 (15)C9—C10—C11—C120.2 (3)
C6—C1—C2—C30.4 (2)N2—N3—C12—C11179.15 (18)
O—C1—C2—N20.7 (2)N2—N3—C12—C7−0.15 (18)
C6—C1—C2—N2−179.96 (15)C10—C11—C12—N3−179.33 (17)
N3—N2—C2—C3−0.9 (2)C10—C11—C12—C7−0.1 (3)
N1—N2—C2—C3179.87 (15)N1—C7—C12—N3−0.04 (19)
N3—N2—C2—C1179.46 (15)C8—C7—C12—N3179.22 (15)
N1—N2—C2—C10.2 (2)N1—C7—C12—C11−179.42 (15)
C1—C2—C3—C40.3 (3)C8—C7—C12—C11−0.2 (3)
N2—C2—C3—C4−179.37 (15)C15—N4—C14—C6177.26 (16)
C2—C3—C4—C5−0.6 (3)C5—C6—C14—N4−13.4 (3)
C2—C3—C4—C13179.92 (16)C1—C6—C14—N4168.64 (17)
C3—C4—C5—C60.2 (3)C14—N4—C15—C20132.8 (2)
C13—C4—C5—C6179.72 (16)C14—N4—C15—C16−47.7 (3)
C4—C5—C6—C10.5 (3)C20—C15—C16—C17−2.4 (3)
C4—C5—C6—C14−177.48 (16)N4—C15—C16—C17178.13 (18)
O—C1—C6—C5178.60 (15)C15—C16—C17—C18−0.6 (3)
C2—C1—C6—C5−0.8 (2)C16—C17—C18—C192.2 (3)
O—C1—C6—C14−3.4 (2)C17—C18—C19—C20−0.7 (3)
C2—C1—C6—C14177.22 (15)C18—C19—C20—C15−2.2 (3)
N2—N1—C7—C120.21 (17)C16—C15—C20—C193.8 (3)
N2—N1—C7—C8−178.95 (17)N4—C15—C20—C19−176.73 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O—H0A···N10.841.852.591 (2)146

Experimental details

Crystal data
Chemical formulaC20H16N4O
Mr328.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)15.7279 (5), 12.3002 (4), 8.4903 (3)
β (°) 104.842 (1)
V (Å3)1587.70 (9)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.48 × 0.37 × 0.21
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.959, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections		15472, 3924, 2874
Rint0.033
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.143, 1.01
No. of reflections3924
No. of parameters228
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O—H0A···N10.841.8522.591 (2)145.9
 

Acknowledgements

We gratefully acknowledge the financial support in part from the National Science Council, Taiwan (NSC99–2113-M-033–007-MY2) and in part from the CYCU Distinctive Research Area project in Chung Yuan Christian University, Taiwan (CYCU–98–CR–CH).

References

First citationBruker (2008). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, M.-J., Li, C.-Y., Tsai, C.-Y. & Ko, B.-T. (2010). Acta Cryst. E66, o2279.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLi, J.-Y., Liu, Y.-C., Lin, C.-H. & Ko, B.-T. (2009). Acta Cryst. E65, o2475.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationLi, C.-Y., Tsai, C.-Y., Lin, C.-H. & Ko, B.-T. (2010). Acta Cryst. E66, o726.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2825
https://doi.org/10.1107/S1600536810040468
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