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

Liu, G.; Wang, J.; Guo, L.; Ruan, W.-J.

doi:10.1107/S1600536808021922

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1552

doi:10.1107/S1600536808021922

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

Ge Liu,^a,^b Jianhui Wang,^a Liqin Guo ^a and Wen-Juan Ruan ^a ^*

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

Experimental

Crystal data

C₂₆H₂₁N₃O₂
M_r = 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 ) T_min = 0.98, T_max = 0.99
10760 measured reflections
3695 independent reflections
3065 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021922/bg2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021922/bg2193Isup2.hkl

checkCIF report

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.

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

	Fig. 1. The structure of the title compound with 30% displacement probability.
	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

C₂₆H₂₁N₃O₂	Z = 2
M_r = 407.46	F(000) = 428
Triclinic, P1	D_x = 1.294 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8299 (18) Å	Cell parameters from 3625 reflections
b = 9.4816 (19) Å	θ = 2.2–27.9°
c = 13.130 (3) Å	µ = 0.08 mm⁻¹
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 tube	3065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2001)	h = −10→10
T_min = 0.98, T_max = 0.99	k = −11→11
10760 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0642P)² + 0.0663P] where P = (F_o² + 2F_c²)/3
3695 reflections	(Δ/σ)_max < 0.001
286 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₆H₂₁N₃O₂	γ = 94.88 (3)°
M_r = 407.46	V = 1046.0 (4) Å³
Triclinic, P1	Z = 2
a = 8.8299 (18) Å	Mo Kα radiation
b = 9.4816 (19) Å	µ = 0.08 mm⁻¹
c = 13.130 (3) Å	T = 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)
T_min = 0.98, T_max = 0.99	R_int = 0.042
10760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.18 e Å⁻³
3695 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O2	0.45524 (17)	0.34953 (15)	0.43121 (12)	0.0511 (4)
O1	0.99294 (14)	0.64418 (13)	0.90770 (11)	0.0365 (3)
H1	1.0207	0.6932	0.8657	0.055*
N1	0.98930 (16)	0.84591 (15)	0.79037 (11)	0.0272 (4)
N2	0.96097 (17)	0.77359 (15)	0.57380 (11)	0.0299 (4)
N3	0.74047 (18)	0.54096 (16)	0.44365 (12)	0.0317 (4)
C1	0.79083 (19)	0.80636 (17)	0.87844 (13)	0.0237 (4)
C2	0.8592 (2)	0.68803 (18)	0.92457 (14)	0.0280 (4)
C3	0.7899 (2)	0.61353 (18)	0.99065 (14)	0.0317 (4)
H3	0.8377	0.5384	1.0237	0.038*
C4	0.6508 (2)	0.65101 (18)	1.00712 (14)	0.0298 (4)
H4	0.6055	0.5997	1.0510	0.036*
C5	0.5756 (2)	0.76395 (18)	0.95990 (13)	0.0267 (4)
C6	0.64834 (19)	0.84052 (18)	0.89718 (13)	0.0258 (4)
H6	0.6013	0.9173	0.8663	0.031*
C7	0.4228 (2)	0.8022 (2)	0.97928 (15)	0.0343 (4)
H7A	0.4454	0.8515	1.0492	0.051*
H7B	0.3529	0.7171	0.9741	0.051*
H7C	0.3730	0.8625	0.9269	0.051*
C8	0.86574 (19)	0.88993 (17)	0.81202 (13)	0.0243 (4)
C9	0.79928 (19)	1.02221 (18)	0.77147 (13)	0.0251 (4)
C10	0.8237 (2)	1.14705 (19)	0.83785 (15)	0.0357 (5)
H10	0.8767	1.1484	0.9100	0.043*
C11	0.7691 (2)	1.2706 (2)	0.79686 (17)	0.0438 (5)
H11	0.7873	1.3548	0.8415	0.053*
C12	0.6882 (2)	1.2690 (2)	0.69028 (18)	0.0430 (5)
H12	0.6520	1.3518	0.6631	0.052*
C13	0.6611 (2)	1.1440 (2)	0.62386 (16)	0.0373 (5)
H13	0.6050	1.1424	0.5522	0.045*
C14	0.71752 (19)	1.02080 (19)	0.66395 (14)	0.0296 (4)
H14	0.7007	0.9372	0.6189	0.036*
C15	1.07804 (19)	0.92923 (18)	0.73647 (13)	0.0260 (4)
C16	1.1816 (2)	1.04669 (19)	0.79313 (15)	0.0324 (4)
H16	1.1853	1.0730	0.8634	0.039*
C17	1.2783 (2)	1.12397 (19)	0.74603 (15)	0.0345 (5)
H17	1.3471	1.2016	0.7846	0.041*
C18	1.2727 (2)	1.08574 (19)	0.64174 (15)	0.0345 (5)
H18	1.3376	1.1376	0.6097	0.041*
C19	1.1705 (2)	0.97020 (19)	0.58480 (15)	0.0324 (4)
H19	1.1664	0.9464	0.5141	0.039*
C20	1.07336 (19)	0.88838 (18)	0.63105 (14)	0.0270 (4)
C21	0.9842 (2)	0.71074 (19)	0.49084 (14)	0.0328 (4)
H21	1.0767	0.7388	0.4736	0.039*
C22	0.8739 (2)	0.59846 (18)	0.42278 (14)	0.0313 (4)
C23	0.8828 (2)	0.5293 (2)	0.32786 (15)	0.0392 (5)
H23	0.9618	0.5477	0.2949	0.047*
C24	0.7517 (2)	0.4276 (2)	0.29150 (15)	0.0407 (5)
H24	0.7272	0.3655	0.2297	0.049*
C25	0.6644 (2)	0.4354 (2)	0.36358 (14)	0.0349 (5)
C26	0.5251 (2)	0.3451 (2)	0.36340 (16)	0.0431 (5)
H26	0.4841	0.2765	0.3057	0.052*
H3A	0.692 (2)	0.574 (2)	0.4957 (16)	0.049 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0440 (9)	0.0476 (9)	0.0613 (10)	−0.0052 (7)	0.0220 (8)	−0.0130 (7)
O1	0.0350 (8)	0.0358 (8)	0.0477 (9)	0.0133 (6)	0.0212 (6)	0.0145 (6)
N1	0.0279 (8)	0.0282 (8)	0.0270 (8)	0.0030 (6)	0.0109 (6)	0.0015 (6)
N2	0.0300 (8)	0.0288 (8)	0.0301 (9)	0.0000 (6)	0.0088 (7)	0.0015 (6)
N3	0.0325 (9)	0.0312 (9)	0.0298 (9)	0.0014 (7)	0.0081 (7)	−0.0021 (7)
C1	0.0251 (9)	0.0229 (9)	0.0213 (9)	0.0005 (7)	0.0054 (7)	−0.0016 (7)
C2	0.0259 (9)	0.0267 (10)	0.0310 (10)	0.0026 (7)	0.0089 (8)	−0.0016 (7)
C3	0.0347 (10)	0.0251 (10)	0.0361 (11)	0.0044 (8)	0.0102 (8)	0.0062 (8)
C4	0.0337 (10)	0.0254 (10)	0.0300 (10)	−0.0038 (7)	0.0111 (8)	0.0015 (7)
C5	0.0259 (9)	0.0262 (9)	0.0260 (10)	−0.0016 (7)	0.0072 (7)	−0.0040 (7)
C6	0.0263 (9)	0.0248 (9)	0.0241 (9)	0.0029 (7)	0.0046 (7)	−0.0013 (7)
C7	0.0324 (10)	0.0353 (11)	0.0369 (11)	0.0031 (8)	0.0132 (8)	0.0033 (8)
C8	0.0257 (9)	0.0243 (9)	0.0208 (9)	−0.0011 (7)	0.0058 (7)	−0.0034 (7)
C9	0.0230 (9)	0.0265 (9)	0.0287 (10)	0.0012 (7)	0.0124 (7)	0.0032 (7)
C10	0.0393 (11)	0.0315 (11)	0.0366 (11)	0.0023 (8)	0.0134 (9)	−0.0014 (8)
C11	0.0491 (13)	0.0261 (11)	0.0610 (15)	0.0041 (9)	0.0250 (11)	−0.0004 (9)
C12	0.0389 (12)	0.0387 (12)	0.0639 (15)	0.0158 (9)	0.0274 (11)	0.0234 (10)
C13	0.0315 (11)	0.0471 (12)	0.0398 (11)	0.0125 (9)	0.0156 (9)	0.0159 (9)
C14	0.0245 (9)	0.0345 (10)	0.0316 (10)	0.0042 (7)	0.0105 (8)	0.0039 (8)
C15	0.0230 (9)	0.0266 (9)	0.0300 (10)	0.0062 (7)	0.0087 (7)	0.0047 (7)
C16	0.0331 (10)	0.0321 (10)	0.0304 (10)	0.0035 (8)	0.0075 (8)	0.0001 (8)
C17	0.0278 (10)	0.0330 (10)	0.0390 (12)	−0.0022 (8)	0.0059 (8)	0.0010 (8)
C18	0.0267 (10)	0.0361 (11)	0.0430 (12)	0.0007 (8)	0.0139 (9)	0.0068 (9)
C19	0.0312 (10)	0.0358 (11)	0.0323 (10)	0.0033 (8)	0.0136 (8)	0.0003 (8)
C20	0.0234 (9)	0.0274 (10)	0.0313 (10)	0.0034 (7)	0.0099 (8)	0.0019 (7)
C21	0.0310 (10)	0.0322 (11)	0.0372 (11)	0.0014 (8)	0.0135 (8)	0.0030 (8)
C22	0.0349 (10)	0.0291 (10)	0.0311 (11)	0.0042 (8)	0.0112 (8)	0.0024 (8)
C23	0.0422 (11)	0.0421 (12)	0.0354 (11)	0.0042 (9)	0.0160 (9)	−0.0019 (9)
C24	0.0433 (12)	0.0437 (12)	0.0316 (11)	0.0035 (9)	0.0082 (9)	−0.0073 (9)
C25	0.0321 (10)	0.0356 (11)	0.0308 (11)	0.0014 (8)	0.0015 (8)	−0.0043 (8)
C26	0.0355 (11)	0.0451 (12)	0.0410 (12)	−0.0003 (9)	0.0040 (10)	−0.0129 (9)

Geometric parameters (Å, º) top

O2—C26	1.218 (2)	C10—H10	0.9300
O1—C2	1.354 (2)	C11—C12	1.379 (3)
O1—H1	0.8200	C11—H11	0.9300
N1—C8	1.296 (2)	C12—C13	1.382 (3)
N1—C15	1.423 (2)	C12—H12	0.9300
N2—C21	1.280 (2)	C13—C14	1.389 (2)
N2—C20	1.420 (2)	C13—H13	0.9300
N3—C22	1.362 (2)	C14—H14	0.9300
N3—C25	1.378 (2)	C15—C20	1.399 (2)
N3—H3A	0.95 (2)	C15—C16	1.399 (2)
C1—C6	1.407 (2)	C16—C17	1.380 (3)
C1—C2	1.413 (2)	C16—H16	0.9300
C1—C8	1.469 (2)	C17—C18	1.378 (2)
C2—C3	1.392 (2)	C17—H17	0.9300
C3—C4	1.376 (2)	C18—C19	1.382 (3)
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.399 (2)	C19—C20	1.398 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.386 (2)	C21—C22	1.442 (3)
C5—C7	1.510 (2)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.392 (2)
C7—H7A	0.9600	C23—C24	1.390 (3)
C7—H7B	0.9600	C23—H23	0.9300
C7—H7C	0.9600	C24—C25	1.381 (3)
C8—C9	1.498 (2)	C24—H24	0.9300
C9—C10	1.383 (2)	C25—C26	1.436 (3)
C9—C14	1.392 (2)	C26—H26	0.9300
C10—C11	1.391 (3)

C2—O1—H1	109.5	C13—C12—H12	120.0
C8—N1—C15	121.20 (15)	C12—C13—C14	120.07 (19)
C21—N2—C20	118.13 (15)	C12—C13—H13	120.0
C22—N3—C25	108.68 (15)	C14—C13—H13	120.0
C22—N3—H3A	128.6 (12)	C13—C14—C9	120.12 (17)
C25—N3—H3A	121.9 (12)	C13—C14—H14	119.9
C6—C1—C2	117.98 (15)	C9—C14—H14	119.9
C6—C1—C8	121.21 (16)	C20—C15—C16	119.75 (16)
C2—C1—C8	120.80 (15)	C20—C15—N1	120.96 (15)
O1—C2—C3	117.93 (16)	C16—C15—N1	119.05 (15)
O1—C2—C1	122.09 (15)	C17—C16—C15	120.85 (17)
C3—C2—C1	119.98 (15)	C17—C16—H16	119.6
C4—C3—C2	120.01 (17)	C15—C16—H16	119.6
C4—C3—H3	120.0	C18—C17—C16	119.75 (17)
C2—C3—H3	120.0	C18—C17—H17	120.1
C3—C4—C5	122.01 (16)	C16—C17—H17	120.1
C3—C4—H4	119.0	C17—C18—C19	119.95 (18)
C5—C4—H4	119.0	C17—C18—H18	120.0
C6—C5—C4	117.52 (16)	C19—C18—H18	120.0
C6—C5—C7	121.70 (16)	C18—C19—C20	121.54 (17)
C4—C5—C7	120.76 (16)	C18—C19—H19	119.2
C5—C6—C1	122.41 (16)	C20—C19—H19	119.2
C5—C6—H6	118.8	C19—C20—C15	118.12 (16)
C1—C6—H6	118.8	C19—C20—N2	123.26 (16)
C5—C7—H7A	109.5	C15—C20—N2	118.41 (15)
C5—C7—H7B	109.5	N2—C21—C22	123.21 (17)
H7A—C7—H7B	109.5	N2—C21—H21	118.4
C5—C7—H7C	109.5	C22—C21—H21	118.4
H7A—C7—H7C	109.5	N3—C22—C23	108.20 (16)
H7B—C7—H7C	109.5	N3—C22—C21	123.94 (16)
N1—C8—C1	118.17 (15)	C23—C22—C21	127.86 (18)
N1—C8—C9	121.81 (15)	C24—C23—C22	107.35 (17)
C1—C8—C9	120.02 (14)	C24—C23—H23	126.3
C10—C9—C14	119.51 (17)	C22—C23—H23	126.3
C10—C9—C8	121.20 (16)	C25—C24—C23	107.77 (17)
C14—C9—C8	119.24 (15)	C25—C24—H24	126.1
C9—C10—C11	120.09 (18)	C23—C24—H24	126.1
C9—C10—H10	120.0	N3—C25—C24	108.00 (17)
C11—C10—H10	120.0	N3—C25—C26	123.92 (17)
C12—C11—C10	120.27 (18)	C24—C25—C26	127.93 (18)
C12—C11—H11	119.9	O2—C26—C25	126.53 (18)
C10—C11—H11	119.9	O2—C26—H26	116.7
C11—C12—C13	119.92 (19)	C25—C26—H26	116.7
C11—C12—H12	120.0

C6—C1—C2—O1	177.55 (14)	C8—C9—C14—C13	−177.17 (15)
C8—C1—C2—O1	−1.8 (2)	C8—N1—C15—C20	−109.03 (19)
C6—C1—C2—C3	−3.2 (2)	C8—N1—C15—C16	76.5 (2)
C8—C1—C2—C3	177.49 (14)	C20—C15—C16—C17	0.7 (3)
O1—C2—C3—C4	−177.69 (15)	N1—C15—C16—C17	175.21 (16)
C1—C2—C3—C4	3.0 (3)	C15—C16—C17—C18	0.3 (3)
C2—C3—C4—C5	−0.6 (3)	C16—C17—C18—C19	−0.1 (3)
C3—C4—C5—C6	−1.6 (2)	C17—C18—C19—C20	−1.1 (3)
C3—C4—C5—C7	179.84 (15)	C18—C19—C20—C15	2.1 (3)
C4—C5—C6—C1	1.4 (2)	C18—C19—C20—N2	176.60 (16)
C7—C5—C6—C1	179.91 (15)	C16—C15—C20—C19	−1.8 (3)
C2—C1—C6—C5	1.0 (2)	N1—C15—C20—C19	−176.24 (15)
C8—C1—C6—C5	−179.68 (14)	C16—C15—C20—N2	−176.62 (15)
C15—N1—C8—C1	−173.10 (14)	N1—C15—C20—N2	9.0 (2)
C15—N1—C8—C9	6.8 (2)	C21—N2—C20—C19	24.6 (3)
C6—C1—C8—N1	−174.23 (14)	C21—N2—C20—C15	−160.85 (16)
C2—C1—C8—N1	5.1 (2)	C20—N2—C21—C22	−176.30 (16)
C6—C1—C8—C9	5.9 (2)	C25—N3—C22—C23	0.3 (2)
C2—C1—C8—C9	−174.80 (14)	C25—N3—C22—C21	−179.04 (17)
N1—C8—C9—C10	−104.20 (19)	N2—C21—C22—N3	−4.9 (3)
C1—C8—C9—C10	75.7 (2)	N2—C21—C22—C23	175.81 (18)
N1—C8—C9—C14	72.9 (2)	N3—C22—C23—C24	−0.2 (2)
C1—C8—C9—C14	−107.18 (17)	C21—C22—C23—C24	179.09 (19)
C14—C9—C10—C11	−1.1 (3)	C22—C23—C24—C25	0.1 (2)
C8—C9—C10—C11	176.07 (16)	C22—N3—C25—C24	−0.3 (2)
C9—C10—C11—C12	1.0 (3)	C22—N3—C25—C26	175.55 (19)
C10—C11—C12—C13	0.1 (3)	C23—C24—C25—N3	0.1 (2)
C11—C12—C13—C14	−1.1 (3)	C23—C24—C25—C26	−175.5 (2)
C12—C13—C14—C9	1.1 (3)	N3—C25—C26—O2	0.8 (3)
C10—C9—C14—C13	0.0 (2)	C24—C25—C26—O2	175.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₁N₃O₂
M_r	407.46
Crystal system, space group	Triclinic, 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)
V (Å³)	1046.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2001)
T_min, T_max	0.98, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	10760, 3695, 3065
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.08
No. of reflections	3695
No. of parameters	286
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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)	147.1

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Nankai University for supporting this work.

References

Ainscough, 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
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Atkins, R., Brewer, G., Kokot, E., Mockler, G. M. & Sinn, E. (1985). Inorg. Chem. 24, 127–134. CSD CrossRef CAS Web of Science Google Scholar
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Olsson, K. & Pernemalm, P.-A. (1979). Acta Chem. Scand. Ser. B, 33, 125–132. CrossRef Web of Science Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2001). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, B.-X., Ruan, W.-J., Yuan, R.-J., Cao, X.-H. & Zhu, Z.-A. (2004). Yingyong Huaxue, 21, 1046–1050. CAS Google Scholar

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Volume 64| Part 8| August 2008| Page o1552

doi:10.1107/S1600536808021922

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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