2-[1-(3-{2-[(2-Hy-droxy-benzyl-idene)amino]-phen-oxy}prop-yl)-1H-1,3-benzodiazol-2-yl]phenol.

In the title compound, C(29)H(25)N(3)O(3), the imine double bond has an E configuration. The dihedral angle between the hy-droxy-phenyl and benzene rings in the imine moiety is 26.95 (9)°, and the dihedral angle between the hy-droxy-phenyl 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 intra-molecular O-H⋯N hydrogen bonds formed between the hy-droxy 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 = 463.52

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.137

S = 1.06

5135 reflections

318 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H25N3O3	F(000) = 976
Mr = 463.52	Dx = 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

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

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(Fo2) + (0.0536P)2 + 0.4485P] where P = (Fo2 + 2Fc2)/3
5135 reflections	(Δ/σ)max = 0.001
318 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.20 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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