2-[1-(3-{2-[(2-Hy­droxy­benzyl­idene)amino]­phen­oxy}prop­yl)-1H-1,3-benzodiazol-2-yl]phenol

Keypour, H.; Tamizi, S.; Dehghanpour, S.; Azadbakht, R.; Khalaj, M.

doi:10.1107/S1600536811005319

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o657-o658

doi:10.1107/S1600536811005319

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2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H-1,3-benzodiazol-2-yl]phenol

Hassan Keypour,^a ^* Sareh Tamizi,^a Saeed Dehghanpour,^b Reza Azadbakht ^c and Mehdi Khalaj ^a,^d

^aFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran, ^bDepartment of Chemistry, Alzahra University, Vanak, Tehran, Iran, ^cDepartment of Chemistry, Payam Noor University, Hamedan, Iran, and ^dDepartment of Chemistry, Islamic Azad University, Buinzahra Branch, Buinzahra, Qazvin, Iran
^*Correspondence e-mail: haskey1@yahoo.com

(Received 30 January 2011; accepted 12 February 2011; online 19 February 2011)

In the title compound, C₂₉H₂₅N₃O₃, the imine double bond has an E configuration. The dihedral angle between the hydroxyphenyl and benzene rings in the imine moiety is 26.95 (9)°, and the dihedral angle between the hydroxyphenyl and benzimidazole rings in the other moiety is 14.83 (9)°. These angles are probably limited to small values as a consequence of two strong intramolecular O—H⋯N hydrogen bonds formed between the hydroxy groups and the imine and imidazole N atoms. The aliphatic chain linking the two ring systems has a gauche conformation, as reflected in C—C—C—O torsion angle of 70.9 (2)°.

Related literature

For related structures, see: Keypour et al. (2009 ). For background information on diimine complexes, see: Mahmoudi et al. (2009 ).

Experimental

Crystal data

C₂₉H₂₅N₃O₃
M_r = 463.52
Monoclinic, P 2₁ /c
a = 9.1097 (6) Å
b = 18.1946 (11) Å
c = 13.7769 (5) Å
β = 93.405 (4)°
V = 2279.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.25 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.866, T_max = 0.993
16359 measured reflections
5135 independent reflections
3083 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.137
S = 1.06
5135 reflections
318 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.84	1.81	2.564 (2)	148
O3—H2O⋯N3	0.84	1.80	2.548 (2)	148

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005319/bh2338sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005319/bh2338Isup2.hkl

checkCIF report

Comment top

In our ongoing studies on the synthesis, structural and spectroscopic characterization of the products derived from N¹-(3-(2-aminophenoxy)propyl)-benzene-1,2-diamine with aldehydes (Keypour et al., 2009; Mahmoudi et al., 2009) we report herein the crystal structure of the title compound, prepared by the reaction of N¹-(3-(2-aminophenoxy)propyl)-benzene-1,2-diamine with salicyl aldehyde.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts the E configuration with respect to the imine C═N bond. Two hydroxyl groups are located close to N atoms, and form strong intramolecular hydrogen bonds (Table 1).

Related literature top

For related structures, see: Keypour et al. (2009). For background information on diimine complexes, see: Mahmoudi et al. (2009).

Experimental top

N¹-(3-(2-aminophenoxy)propyl)benzene-1,2-diamine (0.064 g, 0.25 mmol) in methanol (20 ml) was added dropwise with stirring to a solution of salicylaldehyde (0.061 g, 0.5 mmol) in methanol (30 ml). The mixture was refluxed for 12 h. Then, the solution volume was reduced to 10 ml by evaporation, and a precipitate was formed. This was filtered off, washed with ether, and dried in vacuo. Vapour diffusion of diethyl ether into a methanolic solution of the product afforded yellow crystals in 60% yield.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the structure of the title complex, with displacement ellipsoids drawn at the 50% probability level.

2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H- 1,3-benzodiazol-2-yl]phenol top

Crystal data top

C₂₉H₂₅N₃O₃	F(000) = 976
M_r = 463.52	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16359 reflections
a = 9.1097 (6) Å	θ = 2.7–27.5°
b = 18.1946 (11) Å	µ = 0.09 mm⁻¹
c = 13.7769 (5) Å	T = 150 K
β = 93.405 (4)°	Needle, yellow
V = 2279.5 (2) Å³	0.25 × 0.12 × 0.10 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	5135 independent reflections
Radiation source: fine-focus sealed tube	3083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ϕ scans and ω scans with κ offsets	h = −11→11
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −22→23
T_min = 0.866, T_max = 0.993	l = −17→17
16359 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0536P)² + 0.4485P] where P = (F_o² + 2F_c²)/3
5135 reflections	(Δ/σ)_max = 0.001
318 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³
0 constraints

Crystal data top

C₂₉H₂₅N₃O₃	V = 2279.5 (2) Å³
M_r = 463.52	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1097 (6) Å	µ = 0.09 mm⁻¹
b = 18.1946 (11) Å	T = 150 K
c = 13.7769 (5) Å	0.25 × 0.12 × 0.10 mm
β = 93.405 (4)°

Data collection top

Nonius KappaCCD diffractometer	5135 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3083 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.993	R_int = 0.054
16359 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.137	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
5135 reflections	Δρ_min = −0.20 e Å⁻³
318 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.98262 (18)	0.22668 (8)	0.88875 (9)	0.0465 (4)
H1O	0.9212	0.1922	0.8864	0.070*
O2	0.80830 (16)	0.02045 (7)	0.35975 (9)	0.0369 (4)
O3	0.69646 (17)	−0.13681 (8)	0.49252 (9)	0.0418 (4)
H2O	0.7212	−0.1156	0.4418	0.063*
N1	0.82575 (18)	0.08636 (9)	0.66217 (11)	0.0352 (4)
N2	0.80517 (19)	0.13040 (9)	0.81279 (11)	0.0378 (4)
N3	0.70199 (18)	−0.10938 (9)	0.31140 (11)	0.0323 (4)
C1	0.8674 (2)	0.13987 (11)	0.72906 (13)	0.0348 (5)
C2	0.7258 (2)	0.04118 (11)	0.70695 (14)	0.0355 (5)
C3	0.6454 (2)	−0.01894 (12)	0.67220 (16)	0.0424 (5)
H3A	0.6527	−0.0369	0.6079	0.051*
C4	0.5538 (2)	−0.05139 (12)	0.73642 (17)	0.0461 (6)
H4A	0.4961	−0.0926	0.7155	0.055*
C5	0.5439 (2)	−0.02520 (12)	0.83139 (17)	0.0462 (6)
H5A	0.4805	−0.0492	0.8736	0.055*
C6	0.6241 (2)	0.03446 (12)	0.86451 (16)	0.0428 (5)
H6A	0.6173	0.0520	0.9290	0.051*
C7	0.7156 (2)	0.06849 (11)	0.80071 (14)	0.0371 (5)
C8	0.9683 (2)	0.20146 (11)	0.71522 (14)	0.0342 (5)
C9	1.0249 (2)	0.24102 (12)	0.79778 (14)	0.0358 (5)
C10	1.1272 (2)	0.29677 (12)	0.78825 (15)	0.0406 (5)
H10A	1.1682	0.3211	0.8445	0.049*
C11	1.1694 (2)	0.31703 (12)	0.69784 (16)	0.0433 (5)
H11A	1.2402	0.3549	0.6920	0.052*
C12	1.1092 (2)	0.28247 (12)	0.61553 (15)	0.0411 (5)
H12A	1.1353	0.2979	0.5530	0.049*
C13	1.0116 (2)	0.22574 (11)	0.62434 (14)	0.0375 (5)
H13A	0.9720	0.2021	0.5671	0.045*
C14	0.8752 (2)	0.07122 (11)	0.56509 (13)	0.0354 (5)
H14A	0.8771	0.0174	0.5545	0.042*
H14B	0.9765	0.0900	0.5607	0.042*
C15	0.7747 (2)	0.10687 (12)	0.48571 (13)	0.0372 (5)
H15A	0.6749	0.0856	0.4877	0.045*
H15B	0.7675	0.1602	0.4991	0.045*
C16	0.8287 (2)	0.09626 (11)	0.38527 (14)	0.0375 (5)
H16A	0.7725	0.1280	0.3380	0.045*
H16B	0.9341	0.1095	0.3847	0.045*
C17	0.8190 (2)	0.00152 (11)	0.26392 (13)	0.0319 (5)
C18	0.8766 (2)	0.04669 (12)	0.19473 (14)	0.0382 (5)
H18A	0.9154	0.0936	0.2127	0.046*
C19	0.8774 (2)	0.02298 (12)	0.09868 (15)	0.0420 (5)
H19A	0.9156	0.0542	0.0510	0.050*
C20	0.8233 (2)	−0.04524 (12)	0.07220 (14)	0.0408 (5)
H20A	0.8249	−0.0611	0.0066	0.049*
C21	0.7667 (2)	−0.09051 (12)	0.14125 (14)	0.0367 (5)
H21A	0.7311	−0.1379	0.1230	0.044*
C22	0.7614 (2)	−0.06751 (11)	0.23715 (13)	0.0320 (5)
C23	0.5987 (2)	−0.15625 (11)	0.29380 (14)	0.0344 (5)
H23A	0.5604	−0.1634	0.2288	0.041*
C24	0.5396 (2)	−0.19841 (11)	0.37172 (14)	0.0339 (5)
C25	0.4292 (2)	−0.25061 (12)	0.35230 (16)	0.0403 (5)
H25A	0.3930	−0.2584	0.2870	0.048*
C26	0.3717 (2)	−0.29106 (12)	0.42569 (17)	0.0458 (6)
H26A	0.2965	−0.3263	0.4114	0.055*
C27	0.4258 (2)	−0.27940 (12)	0.52143 (16)	0.0444 (6)
H27A	0.3875	−0.3073	0.5725	0.053*
C28	0.5338 (2)	−0.22813 (12)	0.54275 (15)	0.0407 (5)
H28A	0.5687	−0.2206	0.6083	0.049*
C29	0.5923 (2)	−0.18717 (11)	0.46906 (14)	0.0340 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0556 (11)	0.0529 (11)	0.0310 (8)	−0.0016 (8)	0.0015 (7)	−0.0072 (7)
O2	0.0491 (9)	0.0346 (8)	0.0271 (7)	−0.0053 (7)	0.0029 (6)	−0.0018 (6)
O3	0.0502 (10)	0.0431 (9)	0.0320 (8)	−0.0091 (7)	0.0014 (6)	0.0014 (6)
N1	0.0373 (10)	0.0394 (10)	0.0289 (9)	0.0047 (8)	0.0017 (7)	−0.0045 (7)
N2	0.0435 (11)	0.0402 (11)	0.0298 (9)	0.0039 (9)	0.0032 (7)	−0.0015 (7)
N3	0.0351 (10)	0.0305 (10)	0.0314 (9)	0.0023 (8)	0.0033 (7)	0.0000 (7)
C1	0.0339 (12)	0.0397 (13)	0.0307 (11)	0.0079 (9)	−0.0001 (8)	−0.0026 (9)
C2	0.0312 (12)	0.0353 (12)	0.0401 (12)	0.0057 (9)	0.0023 (9)	0.0017 (9)
C3	0.0427 (13)	0.0416 (14)	0.0423 (13)	0.0072 (11)	−0.0021 (10)	−0.0059 (10)
C4	0.0393 (14)	0.0382 (13)	0.0604 (15)	0.0013 (11)	−0.0010 (11)	−0.0007 (11)
C5	0.0420 (14)	0.0399 (14)	0.0577 (15)	0.0057 (11)	0.0120 (11)	0.0111 (11)
C6	0.0461 (14)	0.0430 (14)	0.0398 (12)	0.0082 (11)	0.0076 (10)	0.0045 (10)
C7	0.0366 (12)	0.0392 (13)	0.0354 (12)	0.0060 (10)	0.0017 (9)	−0.0001 (9)
C8	0.0298 (11)	0.0366 (12)	0.0358 (11)	0.0035 (9)	−0.0005 (8)	−0.0022 (9)
C9	0.0358 (12)	0.0432 (13)	0.0283 (11)	0.0114 (10)	0.0000 (8)	−0.0022 (9)
C10	0.0368 (13)	0.0430 (13)	0.0410 (13)	0.0051 (11)	−0.0046 (9)	−0.0104 (10)
C11	0.0356 (13)	0.0408 (13)	0.0533 (14)	0.0008 (10)	0.0021 (10)	−0.0037 (10)
C12	0.0413 (13)	0.0444 (14)	0.0380 (12)	0.0029 (11)	0.0062 (9)	−0.0009 (10)
C13	0.0387 (13)	0.0415 (13)	0.0321 (11)	0.0024 (10)	0.0001 (9)	−0.0048 (9)
C14	0.0390 (12)	0.0399 (12)	0.0275 (11)	0.0067 (10)	0.0041 (8)	−0.0067 (9)
C15	0.0392 (12)	0.0392 (13)	0.0327 (11)	0.0039 (10)	−0.0007 (9)	−0.0045 (9)
C16	0.0437 (13)	0.0349 (12)	0.0335 (11)	−0.0050 (10)	−0.0003 (9)	−0.0007 (9)
C17	0.0323 (11)	0.0390 (12)	0.0244 (10)	0.0016 (9)	0.0011 (8)	−0.0013 (8)
C18	0.0417 (13)	0.0408 (13)	0.0325 (12)	−0.0043 (10)	0.0051 (9)	0.0012 (9)
C19	0.0448 (14)	0.0487 (14)	0.0334 (12)	−0.0011 (11)	0.0102 (9)	0.0040 (10)
C20	0.0458 (14)	0.0488 (14)	0.0286 (11)	0.0046 (11)	0.0080 (9)	−0.0028 (9)
C21	0.0398 (13)	0.0366 (13)	0.0336 (11)	0.0047 (10)	0.0024 (9)	−0.0041 (9)
C22	0.0308 (11)	0.0342 (12)	0.0310 (11)	0.0050 (9)	0.0027 (8)	0.0025 (8)
C23	0.0376 (12)	0.0333 (12)	0.0322 (11)	0.0058 (10)	0.0019 (9)	−0.0013 (9)
C24	0.0346 (12)	0.0297 (11)	0.0377 (12)	0.0050 (9)	0.0040 (9)	−0.0009 (9)
C25	0.0384 (13)	0.0353 (12)	0.0471 (13)	0.0004 (10)	0.0025 (10)	−0.0056 (10)
C26	0.0382 (14)	0.0345 (13)	0.0649 (16)	−0.0034 (10)	0.0058 (11)	0.0011 (11)
C27	0.0413 (14)	0.0381 (13)	0.0549 (14)	0.0044 (11)	0.0116 (10)	0.0133 (10)
C28	0.0406 (13)	0.0407 (13)	0.0414 (12)	0.0051 (11)	0.0061 (9)	0.0085 (10)
C29	0.0330 (12)	0.0295 (12)	0.0397 (12)	0.0026 (9)	0.0043 (9)	0.0005 (9)

Geometric parameters (Å, º) top

O1—C9	1.358 (2)	C12—H12A	0.9500
O1—H1O	0.8400	C13—H13A	0.9500
O2—C17	1.373 (2)	C14—C15	1.528 (3)
O2—C16	1.433 (2)	C14—H14A	0.9900
O3—C29	1.344 (2)	C14—H14B	0.9900
O3—H2O	0.8400	C15—C16	1.508 (3)
N1—C1	1.378 (2)	C15—H15A	0.9900
N1—C2	1.397 (3)	C15—H15B	0.9900
N1—C14	1.462 (2)	C16—H16A	0.9900
N2—C1	1.326 (2)	C16—H16B	0.9900
N2—C7	1.395 (3)	C17—C18	1.385 (3)
N3—C23	1.282 (2)	C17—C22	1.402 (3)
N3—C22	1.409 (2)	C18—C19	1.392 (3)
C1—C8	1.469 (3)	C18—H18A	0.9500
C2—C3	1.386 (3)	C19—C20	1.377 (3)
C2—C7	1.392 (3)	C19—H19A	0.9500
C3—C4	1.384 (3)	C20—C21	1.381 (3)
C3—H3A	0.9500	C20—H20A	0.9500
C4—C5	1.400 (3)	C21—C22	1.390 (3)
C4—H4A	0.9500	C21—H21A	0.9500
C5—C6	1.371 (3)	C23—C24	1.449 (3)
C5—H5A	0.9500	C23—H23A	0.9500
C6—C7	1.392 (3)	C24—C25	1.397 (3)
C6—H6A	0.9500	C24—C29	1.412 (3)
C8—C13	1.406 (3)	C25—C26	1.379 (3)
C8—C9	1.417 (3)	C25—H25A	0.9500
C9—C10	1.388 (3)	C26—C27	1.397 (3)
C10—C11	1.376 (3)	C26—H26A	0.9500
C10—H10A	0.9500	C27—C28	1.374 (3)
C11—C12	1.381 (3)	C27—H27A	0.9500
C11—H11A	0.9500	C28—C29	1.391 (3)
C12—C13	1.372 (3)	C28—H28A	0.9500

C9—O1—H1O	109.5	H14A—C14—H14B	107.9
C17—O2—C16	117.50 (14)	C16—C15—C14	112.85 (17)
C29—O3—H2O	109.5	C16—C15—H15A	109.0
C1—N1—C2	106.32 (16)	C14—C15—H15A	109.0
C1—N1—C14	131.09 (17)	C16—C15—H15B	109.0
C2—N1—C14	122.48 (16)	C14—C15—H15B	109.0
C1—N2—C7	106.17 (16)	H15A—C15—H15B	107.8
C23—N3—C22	122.11 (16)	O2—C16—C15	107.68 (16)
N2—C1—N1	112.02 (18)	O2—C16—H16A	110.2
N2—C1—C8	121.00 (17)	C15—C16—H16A	110.2
N1—C1—C8	126.98 (18)	O2—C16—H16B	110.2
C3—C2—C7	122.6 (2)	C15—C16—H16B	110.2
C3—C2—N1	131.05 (19)	H16A—C16—H16B	108.5
C7—C2—N1	106.32 (18)	O2—C17—C18	124.33 (18)
C4—C3—C2	116.2 (2)	O2—C17—C22	115.51 (17)
C4—C3—H3A	121.9	C18—C17—C22	120.12 (17)
C2—C3—H3A	121.9	C17—C18—C19	119.6 (2)
C3—C4—C5	121.8 (2)	C17—C18—H18A	120.2
C3—C4—H4A	119.1	C19—C18—H18A	120.2
C5—C4—H4A	119.1	C20—C19—C18	120.6 (2)
C6—C5—C4	121.2 (2)	C20—C19—H19A	119.7
C6—C5—H5A	119.4	C18—C19—H19A	119.7
C4—C5—H5A	119.4	C19—C20—C21	119.83 (19)
C5—C6—C7	118.0 (2)	C19—C20—H20A	120.1
C5—C6—H6A	121.0	C21—C20—H20A	120.1
C7—C6—H6A	121.0	C20—C21—C22	120.7 (2)
C6—C7—C2	120.2 (2)	C20—C21—H21A	119.6
C6—C7—N2	130.68 (19)	C22—C21—H21A	119.6
C2—C7—N2	109.13 (17)	C21—C22—C17	119.08 (18)
C13—C8—C9	116.56 (19)	C21—C22—N3	124.35 (18)
C13—C8—C1	124.48 (18)	C17—C22—N3	116.57 (16)
C9—C8—C1	118.95 (18)	N3—C23—C24	120.85 (18)
O1—C9—C10	117.15 (18)	N3—C23—H23A	119.6
O1—C9—C8	122.22 (19)	C24—C23—H23A	119.6
C10—C9—C8	120.63 (18)	C25—C24—C29	118.71 (18)
C11—C10—C9	120.45 (19)	C25—C24—C23	120.85 (18)
C11—C10—H10A	119.8	C29—C24—C23	120.43 (18)
C9—C10—H10A	119.8	C26—C25—C24	121.5 (2)
C10—C11—C12	120.2 (2)	C26—C25—H25A	119.2
C10—C11—H11A	119.9	C24—C25—H25A	119.2
C12—C11—H11A	119.9	C25—C26—C27	118.9 (2)
C13—C12—C11	119.8 (2)	C25—C26—H26A	120.6
C13—C12—H12A	120.1	C27—C26—H26A	120.6
C11—C12—H12A	120.1	C28—C27—C26	120.9 (2)
C12—C13—C8	122.18 (18)	C28—C27—H27A	119.6
C12—C13—H13A	118.9	C26—C27—H27A	119.6
C8—C13—H13A	118.9	C27—C28—C29	120.5 (2)
N1—C14—C15	111.78 (16)	C27—C28—H28A	119.7
N1—C14—H14A	109.3	C29—C28—H28A	119.7
C15—C14—H14A	109.3	O3—C29—C28	119.03 (18)
N1—C14—H14B	109.3	O3—C29—C24	121.48 (18)
C15—C14—H14B	109.3	C28—C29—C24	119.48 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.84	1.81	2.564 (2)	148
O3—H2O···N3	0.84	1.80	2.548 (2)	148

Experimental details

Crystal data
Chemical formula	C₂₉H₂₅N₃O₃
M_r	463.52
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.1097 (6), 18.1946 (11), 13.7769 (5)
β (°)	93.405 (4)
V (Å³)	2279.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.866, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	16359, 5135, 3083
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.137, 1.06
No. of reflections	5135
No. of parameters	318
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.84	1.81	2.564 (2)	148
O3—H2O···N3	0.84	1.80	2.548 (2)	148

Acknowledgements

We are grateful to Bu-Ali Sina and Alzahra Universities for financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Keypour, H., Azadbakht, R., Salehzadeh, S., Rudbari, H. A. & Adams, H. (2009). Tetrahedron Lett. 50, 169–171. Web of Science CSD CrossRef CAS Google Scholar
Mahmoudi, A., Dehghanpour, S., Khalaj, M. & Pakravan, S. (2009). Acta Cryst. E65, m889. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Pages o657-o658

doi:10.1107/S1600536811005319

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

2-[1-(3-{2-[(2-Hy­dr­oxy­benzyl­­idene)amino]­phen­­oxy}prop­yl)-1H-1,3-benzo­diazol-2-yl]phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H-1,3-benzodiazol-2-yl]phenol