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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-{2-[(2-Hy­droxy-5-methyl­phen­yl)(phenyl)methyl­ene­amino]phenyl­imino­meth­yl}­pyrrole-2-carbaldehyde

aDepartment of Chemistry, Nankai University, Tianjin 300071, People's Republic of China, and bChifeng University, Chifeng 024000, People's Republic of China
*Correspondence e-mail: wjruan@nankai.edu.cn

(Received 6 June 2008; accepted 14 July 2008; online 19 July 2008)

The title compound, C26H21N3O2, is an unsymmetrical tetra­dentate Schiff base ligand. The hydr­oxy group forms an intra­molecular O—H⋯N hydrogen bond with an adjacent N atom. An inter­molecular N—H⋯O hydrogen bond creates centrosymmetric dimers in the crystal packing.

Related literature

For background, see: Ainscough et al. (1995[Ainscough, E. W., Brodie, A. M., Dobbs, A., Ranford, J. D. & Waters, J. M. (1995). Inorg. Chim. Acta, 236, 83-88.]); Aruffo et al. (1984[Aruffo, A. A., Murphy, T. B., Johnson, D. K., Rose, N. J. & Schomaker, V. (1984). Acta Cryst. C40, 1164-1169.]). For further synthetic details, see: Atkins et al. (1985[Atkins, R., Brewer, G., Kokot, E., Mockler, G. M. & Sinn, E. (1985). Inorg. Chem. 24, 127-134.]); Miller & Olsson (1981[Miller, R. & Olsson, K. (1981). Acta Chem. Scand. Ser. B, 35, 303-310.]); Olsson & Pernemalm (1979[Olsson, K. & Pernemalm, P.-A. (1979). Acta Chem. Scand. Ser. B, 33, 125-132.]); Zhu et al. (2004[Zhu, B.-X., Ruan, W.-J., Yuan, R.-J., Cao, X.-H. & Zhu, Z.-A. (2004). Yingyong Huaxue, 21, 1046-1050.]).

[Scheme 1]

Experimental

Crystal data
  • C26H21N3O2

  • Mr = 407.46

  • Triclinic, [P \overline 1]

  • a = 8.8299 (18) Å

  • b = 9.4816 (19) Å

  • c = 13.130 (3) Å

  • α = 94.05 (3)°

  • β = 106.32 (3)°

  • γ = 94.88 (3)°

  • V = 1046.0 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 (2) K

  • 0.22 × 0.16 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001[Rigaku/MSC (2001). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.98, Tmax = 0.99

  • 10760 measured reflections

  • 3695 independent reflections

  • 3065 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.129

  • S = 1.08

  • 3695 reflections

  • 286 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯O2i 0.95 (2) 1.98 (2) 2.902 (2) 164.2 (18)
O1—H1⋯N1 0.82 1.81 2.536 (2) 147
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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


Comment top

Unsymmetrical Schiff base ligands have been widely investigated due to their structural versatility; specially their metal complexes have been of interest to chemists (Aruffo et al., 1984; Ainscough et al.,1995). In the course of the synthesis of one such a complex (Zhu et al., 2004; Atkins et al.,1985), single crystals of the title compound C26H21N3O2 (I) were obtained, and its crystal and molecular structure is reported here (Fig.1). An intermolecular N—H···O hydrogen bond is formed between the H(pyrrole) atom of one molecule and O(aldehyde) of an adjacent molecule (Table 1), giving raise to centrosymmetric dimers in the crystal packing, piled as columnar arrays along a, as shown in Fig. 2

Moreover, the hydroxy group is involved in an intramolecular O—H···N hydrogen bond (Table 1, Fig.1), though which atoms O1, H1, N1, C8, C1 and C2 form a six-membered ring.

Related literature top

For background, see: Ainscough et al. (1995); Aruffo et al. (1984). For further synthetic details, see: Atkins et al. (1985); Miller & Olsson (1981); Olsso & Pernemalm (1979); Zhu et al. (2004).

Experimental top

To a solution of 2-[(2-Aminophenyl)(phenyl)methyl]-4-methylphenol (0.2 mmol)(Atkins et al.,1985) in toluene (20 ml) was added pyrrole-2,5-dicarboxaldehyde (0.2 mmol)(Miller & Olsson, 1981; Olsso & Pernemalm, 1979) the mixture was stired and refluxed for two hours, then cooled. Rotary evaporation of solvent yielded the crude product; after chromatographic fractionating, it was recrystallized from the mixture of dichloromethane and hexane. Orange columnar crystals were obtained by evaporating the solvent at room temperature for about a week. yield: 53%, mp = 175°. Anal. for (C26H21N3O2), Calc. C, 76.64; H, 5.19; N, 10.31; Found: C, 76.12; H, 5.62; N, 10.19.

Refinement top

The H atoms (except H3A attached to N3) were positioned geometrically and allowed to ride on their parent atoms, with C—H=0.93Å and Uiso(H)=1.2Ueq(C) for the aromatic and pyrrole ring H atoms, C—H=0.96Å, and Uiso(H)=1.5Ueq(C) for the methyl H atoms, O-H: 0.82Å, Uiso(H)=1.5Ueq(O). H3A was found in the difference Fourier and refined freely with isotropic displacement parameters.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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 structure of the title compound with 30% displacement probability.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing dimers piled along a. Hydrogen bonds shown as dashed lines.
5-{2-[(2-Hydroxy-5- methylphenyl)(phenyl)methyleneamino]phenyliminomethyl}pyrrole-2-carbaldehyde top
Crystal data top
C26H21N3O2Z = 2
Mr = 407.46F(000) = 428
Triclinic, P1Dx = 1.294 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8299 (18) ÅCell parameters from 3625 reflections
b = 9.4816 (19) Åθ = 2.2–27.9°
c = 13.130 (3) ŵ = 0.08 mm1
α = 94.05 (3)°T = 113 K
β = 106.32 (3)°Block, orange
γ = 94.88 (3)°0.22 × 0.16 × 0.12 mm
V = 1046.0 (4) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
3695 independent reflections
Radiation source: fine-focus sealed tube3065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2001)
h = 1010
Tmin = 0.98, Tmax = 0.99k = 1111
10760 measured reflectionsl = 1515
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.0663P]
where P = (Fo2 + 2Fc2)/3
3695 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C26H21N3O2γ = 94.88 (3)°
Mr = 407.46V = 1046.0 (4) Å3
Triclinic, P1Z = 2
a = 8.8299 (18) ÅMo Kα radiation
b = 9.4816 (19) ŵ = 0.08 mm1
c = 13.130 (3) ÅT = 113 K
α = 94.05 (3)°0.22 × 0.16 × 0.12 mm
β = 106.32 (3)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
3695 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2001)
3065 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 0.99Rint = 0.042
10760 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.18 e Å3
3695 reflectionsΔρmin = 0.25 e Å3
286 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
O20.45524 (17)0.34953 (15)0.43121 (12)0.0511 (4)
O10.99294 (14)0.64418 (13)0.90770 (11)0.0365 (3)
H11.02070.69320.86570.055*
N10.98930 (16)0.84591 (15)0.79037 (11)0.0272 (4)
N20.96097 (17)0.77359 (15)0.57380 (11)0.0299 (4)
N30.74047 (18)0.54096 (16)0.44365 (12)0.0317 (4)
C10.79083 (19)0.80636 (17)0.87844 (13)0.0237 (4)
C20.8592 (2)0.68803 (18)0.92457 (14)0.0280 (4)
C30.7899 (2)0.61353 (18)0.99065 (14)0.0317 (4)
H30.83770.53841.02370.038*
C40.6508 (2)0.65101 (18)1.00712 (14)0.0298 (4)
H40.60550.59971.05100.036*
C50.5756 (2)0.76395 (18)0.95990 (13)0.0267 (4)
C60.64834 (19)0.84052 (18)0.89718 (13)0.0258 (4)
H60.60130.91730.86630.031*
C70.4228 (2)0.8022 (2)0.97928 (15)0.0343 (4)
H7A0.44540.85151.04920.051*
H7B0.35290.71710.97410.051*
H7C0.37300.86250.92690.051*
C80.86574 (19)0.88993 (17)0.81202 (13)0.0243 (4)
C90.79928 (19)1.02221 (18)0.77147 (13)0.0251 (4)
C100.8237 (2)1.14705 (19)0.83785 (15)0.0357 (5)
H100.87671.14840.91000.043*
C110.7691 (2)1.2706 (2)0.79686 (17)0.0438 (5)
H110.78731.35480.84150.053*
C120.6882 (2)1.2690 (2)0.69028 (18)0.0430 (5)
H120.65201.35180.66310.052*
C130.6611 (2)1.1440 (2)0.62386 (16)0.0373 (5)
H130.60501.14240.55220.045*
C140.71752 (19)1.02080 (19)0.66395 (14)0.0296 (4)
H140.70070.93720.61890.036*
C151.07804 (19)0.92923 (18)0.73647 (13)0.0260 (4)
C161.1816 (2)1.04669 (19)0.79313 (15)0.0324 (4)
H161.18531.07300.86340.039*
C171.2783 (2)1.12397 (19)0.74603 (15)0.0345 (5)
H171.34711.20160.78460.041*
C181.2727 (2)1.08574 (19)0.64174 (15)0.0345 (5)
H181.33761.13760.60970.041*
C191.1705 (2)0.97020 (19)0.58480 (15)0.0324 (4)
H191.16640.94640.51410.039*
C201.07336 (19)0.88838 (18)0.63105 (14)0.0270 (4)
C210.9842 (2)0.71074 (19)0.49084 (14)0.0328 (4)
H211.07670.73880.47360.039*
C220.8739 (2)0.59846 (18)0.42278 (14)0.0313 (4)
C230.8828 (2)0.5293 (2)0.32786 (15)0.0392 (5)
H230.96180.54770.29490.047*
C240.7517 (2)0.4276 (2)0.29150 (15)0.0407 (5)
H240.72720.36550.22970.049*
C250.6644 (2)0.4354 (2)0.36358 (14)0.0349 (5)
C260.5251 (2)0.3451 (2)0.36340 (16)0.0431 (5)
H260.48410.27650.30570.052*
H3A0.692 (2)0.574 (2)0.4957 (16)0.049 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0440 (9)0.0476 (9)0.0613 (10)0.0052 (7)0.0220 (8)0.0130 (7)
O10.0350 (8)0.0358 (8)0.0477 (9)0.0133 (6)0.0212 (6)0.0145 (6)
N10.0279 (8)0.0282 (8)0.0270 (8)0.0030 (6)0.0109 (6)0.0015 (6)
N20.0300 (8)0.0288 (8)0.0301 (9)0.0000 (6)0.0088 (7)0.0015 (6)
N30.0325 (9)0.0312 (9)0.0298 (9)0.0014 (7)0.0081 (7)0.0021 (7)
C10.0251 (9)0.0229 (9)0.0213 (9)0.0005 (7)0.0054 (7)0.0016 (7)
C20.0259 (9)0.0267 (10)0.0310 (10)0.0026 (7)0.0089 (8)0.0016 (7)
C30.0347 (10)0.0251 (10)0.0361 (11)0.0044 (8)0.0102 (8)0.0062 (8)
C40.0337 (10)0.0254 (10)0.0300 (10)0.0038 (7)0.0111 (8)0.0015 (7)
C50.0259 (9)0.0262 (9)0.0260 (10)0.0016 (7)0.0072 (7)0.0040 (7)
C60.0263 (9)0.0248 (9)0.0241 (9)0.0029 (7)0.0046 (7)0.0013 (7)
C70.0324 (10)0.0353 (11)0.0369 (11)0.0031 (8)0.0132 (8)0.0033 (8)
C80.0257 (9)0.0243 (9)0.0208 (9)0.0011 (7)0.0058 (7)0.0034 (7)
C90.0230 (9)0.0265 (9)0.0287 (10)0.0012 (7)0.0124 (7)0.0032 (7)
C100.0393 (11)0.0315 (11)0.0366 (11)0.0023 (8)0.0134 (9)0.0014 (8)
C110.0491 (13)0.0261 (11)0.0610 (15)0.0041 (9)0.0250 (11)0.0004 (9)
C120.0389 (12)0.0387 (12)0.0639 (15)0.0158 (9)0.0274 (11)0.0234 (10)
C130.0315 (11)0.0471 (12)0.0398 (11)0.0125 (9)0.0156 (9)0.0159 (9)
C140.0245 (9)0.0345 (10)0.0316 (10)0.0042 (7)0.0105 (8)0.0039 (8)
C150.0230 (9)0.0266 (9)0.0300 (10)0.0062 (7)0.0087 (7)0.0047 (7)
C160.0331 (10)0.0321 (10)0.0304 (10)0.0035 (8)0.0075 (8)0.0001 (8)
C170.0278 (10)0.0330 (10)0.0390 (12)0.0022 (8)0.0059 (8)0.0010 (8)
C180.0267 (10)0.0361 (11)0.0430 (12)0.0007 (8)0.0139 (9)0.0068 (9)
C190.0312 (10)0.0358 (11)0.0323 (10)0.0033 (8)0.0136 (8)0.0003 (8)
C200.0234 (9)0.0274 (10)0.0313 (10)0.0034 (7)0.0099 (8)0.0019 (7)
C210.0310 (10)0.0322 (11)0.0372 (11)0.0014 (8)0.0135 (8)0.0030 (8)
C220.0349 (10)0.0291 (10)0.0311 (11)0.0042 (8)0.0112 (8)0.0024 (8)
C230.0422 (11)0.0421 (12)0.0354 (11)0.0042 (9)0.0160 (9)0.0019 (9)
C240.0433 (12)0.0437 (12)0.0316 (11)0.0035 (9)0.0082 (9)0.0073 (9)
C250.0321 (10)0.0356 (11)0.0308 (11)0.0014 (8)0.0015 (8)0.0043 (8)
C260.0355 (11)0.0451 (12)0.0410 (12)0.0003 (9)0.0040 (10)0.0129 (9)
Geometric parameters (Å, º) top
O2—C261.218 (2)C10—H100.9300
O1—C21.354 (2)C11—C121.379 (3)
O1—H10.8200C11—H110.9300
N1—C81.296 (2)C12—C131.382 (3)
N1—C151.423 (2)C12—H120.9300
N2—C211.280 (2)C13—C141.389 (2)
N2—C201.420 (2)C13—H130.9300
N3—C221.362 (2)C14—H140.9300
N3—C251.378 (2)C15—C201.399 (2)
N3—H3A0.95 (2)C15—C161.399 (2)
C1—C61.407 (2)C16—C171.380 (3)
C1—C21.413 (2)C16—H160.9300
C1—C81.469 (2)C17—C181.378 (2)
C2—C31.392 (2)C17—H170.9300
C3—C41.376 (2)C18—C191.382 (3)
C3—H30.9300C18—H180.9300
C4—C51.399 (2)C19—C201.398 (3)
C4—H40.9300C19—H190.9300
C5—C61.386 (2)C21—C221.442 (3)
C5—C71.510 (2)C21—H210.9300
C6—H60.9300C22—C231.392 (2)
C7—H7A0.9600C23—C241.390 (3)
C7—H7B0.9600C23—H230.9300
C7—H7C0.9600C24—C251.381 (3)
C8—C91.498 (2)C24—H240.9300
C9—C101.383 (2)C25—C261.436 (3)
C9—C141.392 (2)C26—H260.9300
C10—C111.391 (3)
C2—O1—H1109.5C13—C12—H12120.0
C8—N1—C15121.20 (15)C12—C13—C14120.07 (19)
C21—N2—C20118.13 (15)C12—C13—H13120.0
C22—N3—C25108.68 (15)C14—C13—H13120.0
C22—N3—H3A128.6 (12)C13—C14—C9120.12 (17)
C25—N3—H3A121.9 (12)C13—C14—H14119.9
C6—C1—C2117.98 (15)C9—C14—H14119.9
C6—C1—C8121.21 (16)C20—C15—C16119.75 (16)
C2—C1—C8120.80 (15)C20—C15—N1120.96 (15)
O1—C2—C3117.93 (16)C16—C15—N1119.05 (15)
O1—C2—C1122.09 (15)C17—C16—C15120.85 (17)
C3—C2—C1119.98 (15)C17—C16—H16119.6
C4—C3—C2120.01 (17)C15—C16—H16119.6
C4—C3—H3120.0C18—C17—C16119.75 (17)
C2—C3—H3120.0C18—C17—H17120.1
C3—C4—C5122.01 (16)C16—C17—H17120.1
C3—C4—H4119.0C17—C18—C19119.95 (18)
C5—C4—H4119.0C17—C18—H18120.0
C6—C5—C4117.52 (16)C19—C18—H18120.0
C6—C5—C7121.70 (16)C18—C19—C20121.54 (17)
C4—C5—C7120.76 (16)C18—C19—H19119.2
C5—C6—C1122.41 (16)C20—C19—H19119.2
C5—C6—H6118.8C19—C20—C15118.12 (16)
C1—C6—H6118.8C19—C20—N2123.26 (16)
C5—C7—H7A109.5C15—C20—N2118.41 (15)
C5—C7—H7B109.5N2—C21—C22123.21 (17)
H7A—C7—H7B109.5N2—C21—H21118.4
C5—C7—H7C109.5C22—C21—H21118.4
H7A—C7—H7C109.5N3—C22—C23108.20 (16)
H7B—C7—H7C109.5N3—C22—C21123.94 (16)
N1—C8—C1118.17 (15)C23—C22—C21127.86 (18)
N1—C8—C9121.81 (15)C24—C23—C22107.35 (17)
C1—C8—C9120.02 (14)C24—C23—H23126.3
C10—C9—C14119.51 (17)C22—C23—H23126.3
C10—C9—C8121.20 (16)C25—C24—C23107.77 (17)
C14—C9—C8119.24 (15)C25—C24—H24126.1
C9—C10—C11120.09 (18)C23—C24—H24126.1
C9—C10—H10120.0N3—C25—C24108.00 (17)
C11—C10—H10120.0N3—C25—C26123.92 (17)
C12—C11—C10120.27 (18)C24—C25—C26127.93 (18)
C12—C11—H11119.9O2—C26—C25126.53 (18)
C10—C11—H11119.9O2—C26—H26116.7
C11—C12—C13119.92 (19)C25—C26—H26116.7
C11—C12—H12120.0
C6—C1—C2—O1177.55 (14)C8—C9—C14—C13177.17 (15)
C8—C1—C2—O11.8 (2)C8—N1—C15—C20109.03 (19)
C6—C1—C2—C33.2 (2)C8—N1—C15—C1676.5 (2)
C8—C1—C2—C3177.49 (14)C20—C15—C16—C170.7 (3)
O1—C2—C3—C4177.69 (15)N1—C15—C16—C17175.21 (16)
C1—C2—C3—C43.0 (3)C15—C16—C17—C180.3 (3)
C2—C3—C4—C50.6 (3)C16—C17—C18—C190.1 (3)
C3—C4—C5—C61.6 (2)C17—C18—C19—C201.1 (3)
C3—C4—C5—C7179.84 (15)C18—C19—C20—C152.1 (3)
C4—C5—C6—C11.4 (2)C18—C19—C20—N2176.60 (16)
C7—C5—C6—C1179.91 (15)C16—C15—C20—C191.8 (3)
C2—C1—C6—C51.0 (2)N1—C15—C20—C19176.24 (15)
C8—C1—C6—C5179.68 (14)C16—C15—C20—N2176.62 (15)
C15—N1—C8—C1173.10 (14)N1—C15—C20—N29.0 (2)
C15—N1—C8—C96.8 (2)C21—N2—C20—C1924.6 (3)
C6—C1—C8—N1174.23 (14)C21—N2—C20—C15160.85 (16)
C2—C1—C8—N15.1 (2)C20—N2—C21—C22176.30 (16)
C6—C1—C8—C95.9 (2)C25—N3—C22—C230.3 (2)
C2—C1—C8—C9174.80 (14)C25—N3—C22—C21179.04 (17)
N1—C8—C9—C10104.20 (19)N2—C21—C22—N34.9 (3)
C1—C8—C9—C1075.7 (2)N2—C21—C22—C23175.81 (18)
N1—C8—C9—C1472.9 (2)N3—C22—C23—C240.2 (2)
C1—C8—C9—C14107.18 (17)C21—C22—C23—C24179.09 (19)
C14—C9—C10—C111.1 (3)C22—C23—C24—C250.1 (2)
C8—C9—C10—C11176.07 (16)C22—N3—C25—C240.3 (2)
C9—C10—C11—C121.0 (3)C22—N3—C25—C26175.55 (19)
C10—C11—C12—C130.1 (3)C23—C24—C25—N30.1 (2)
C11—C12—C13—C141.1 (3)C23—C24—C25—C26175.5 (2)
C12—C13—C14—C91.1 (3)N3—C25—C26—O20.8 (3)
C10—C9—C14—C130.0 (2)C24—C25—C26—O2175.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.95 (2)1.98 (2)2.902 (2)164.2 (18)
O1—H1···N10.821.812.536 (2)147
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H21N3O2
Mr407.46
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)8.8299 (18), 9.4816 (19), 13.130 (3)
α, β, γ (°)94.05 (3), 106.32 (3), 94.88 (3)
V3)1046.0 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.22 × 0.16 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID-S
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2001)
Tmin, Tmax0.98, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
10760, 3695, 3065
Rint0.042
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.129, 1.08
No. of reflections3695
No. of parameters286
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.25

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.95 (2)1.98 (2)2.902 (2)164.2 (18)
O1—H1···N10.821.812.536 (2)147.1
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

The authors thank Nankai University for supporting this work.

References

First citationAinscough, E. W., Brodie, A. M., Dobbs, A., Ranford, J. D. & Waters, J. M. (1995). Inorg. Chim. Acta, 236, 83–88.  CrossRef CAS Web of Science Google Scholar
First citationAruffo, A. A., Murphy, T. B., Johnson, D. K., Rose, N. J. & Schomaker, V. (1984). Acta Cryst. C40, 1164–1169.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationAtkins, R., Brewer, G., Kokot, E., Mockler, G. M. & Sinn, E. (1985). Inorg. Chem. 24, 127–134.  CSD CrossRef CAS Web of Science Google Scholar
First citationMiller, R. & Olsson, K. (1981). Acta Chem. Scand. Ser. B, 35, 303–310.  CrossRef Web of Science Google Scholar
First citationOlsson, K. & Pernemalm, P.-A. (1979). Acta Chem. Scand. Ser. B, 33, 125–132.  CrossRef Web of Science Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2001). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhu, B.-X., Ruan, W.-J., Yuan, R.-J., Cao, X.-H. & Zhu, Z.-A. (2004). Yingyong Huaxue, 21, 1046–1050.  CAS 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds