2,2'-[(Propane-1,3-diyldinitrilo)bis-(phenyl-methyl-idyne)]diphenol.

In the title mol-ecule, C(29)H(26)N(2)O(2), there are two strong intra-molecular O-H⋯N hydrogen bonds involving the hydr-oxy and imine groups, forming S(6) ring motifs. The dihedral angles between adjacent phenyl rings and phenol-containing planes are 85.27 (19) and 91.38 (18)°. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds connect mol-ecules into a two-dimensional network.

Related literature

The title compound forms part of the group of Schiff bases with a similar method of synthesis as described in Schilf et al. (2007 ▶). The inter­molecular hydrogen bonds O—H⋯N between the hydr­oxy and imine are common to this type of compound as shown with the series of compounds reported by Fernández et al. (2001 ▶); Kabak (2003 ▶); Wojciechowski et al. (2001 ▶); Dey et al. (2001 ▶); Koşar, et al. (2004 ▶); Lu, et al. (2008 ▶); Qiu & Zhao (2008 ▶); Montazerozohori et al. (2009 ▶); Corden et al. (1996 ▶). For a decription of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C29H26N2O2

M = 434.52

Monoclinic,

a = 18.226 (2) Å

b = 8.2303 (9) Å

c = 18.642 (2) Å

β = 119.086 (5)°

V = 2443.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.7 × 0.5 × 0.28 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

21350 measured reflections

5896 independent reflections

3749 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.173

S = 1.03

5896 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART-NT (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011189/lh5012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011189/lh5012Isup2.hkl

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

C29H26N2O2	F(000) = 920
Mr = 434.52	Dx = 1.181 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 21350 reflections
a = 18.226 (2) Å	θ = 2.1–23.0°
b = 8.2303 (9) Å	µ = 0.07 mm−1
c = 18.642 (2) Å	T = 293 K
β = 119.086 (5)°	Block, yellow
V = 2443.7 (5) Å3	0.7 × 0.5 × 0.28 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	Rint = 0.071
φ and ω scans	θmax = 28°, θmin = 1.3°
21350 measured reflections	h = −19→24
5896 independent reflections	k = −10→10
3749 reflections with I > 2σ(I)	l = −24→20

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0897P)2 + 0.2258P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.173	(Δ/σ)max = 0.002
S = 1.03	Δρmax = 0.23 e Å−3
5896 reflections	Δρmin = −0.36 e Å−3
300 parameters

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.17087 (13)	0.1655 (3)	0.08228 (11)	0.0718 (5)
H1	0.1926	0.2672	0.0813	0.086*
C2	0.15625 (16)	0.0517 (3)	0.02117 (14)	0.0940 (7)
H2	0.1689	0.0776	−0.0201	0.113*
C3	0.12367 (14)	−0.0961 (3)	0.02162 (16)	0.0947 (8)
H3	0.1142	−0.1708	−0.0194	0.114*
C4	0.10480 (16)	−0.1362 (3)	0.08146 (16)	0.0960 (7)
H4	0.0823	−0.2377	0.0812	0.115*
C5	0.11925 (13)	−0.0247 (3)	0.14328 (13)	0.0759 (5)
H5	0.1062	−0.0519	0.1842	0.091*
C6	0.15300 (9)	0.12641 (19)	0.14400 (9)	0.0501 (4)
C7	0.17057 (8)	0.24201 (18)	0.21320 (9)	0.0457 (3)
C8	0.10782 (9)	0.36732 (18)	0.20194 (9)	0.0476 (3)
C9	0.03699 (10)	0.3944 (2)	0.12497 (11)	0.0612 (4)
H9	0.0291	0.3308	0.0805	0.073*
C10	−0.02150 (12)	0.5138 (3)	0.11365 (13)	0.0775 (6)
H10	−0.0675	0.5312	0.062	0.093*
C11	−0.01072 (13)	0.6066 (3)	0.17994 (16)	0.0826 (6)
H11	−0.05	0.6861	0.1726	0.099*
C12	0.05729 (13)	0.5829 (2)	0.25660 (14)	0.0735 (5)
H12	0.0632	0.6461	0.3004	0.088*
C13	0.11810 (10)	0.4642 (2)	0.26941 (10)	0.0548 (4)
C14	0.30624 (10)	0.1168 (2)	0.29798 (11)	0.0637 (4)
H14A	0.3103	0.1037	0.2483	0.076*
H14B	0.2935	0.0117	0.3128	0.076*
C15	0.38907 (10)	0.1788 (2)	0.36662 (10)	0.0590 (4)
H15A	0.385	0.1869	0.4165	0.071*
H15B	0.3992	0.287	0.3528	0.071*
C16	0.46364 (10)	0.0702 (2)	0.38294 (10)	0.0606 (4)
H16A	0.5125	0.1034	0.4336	0.073*
H16B	0.4508	−0.0416	0.3891	0.073*
C17	0.66693 (10)	0.2305 (2)	0.45511 (10)	0.0602 (4)
H17	0.6442	0.3306	0.4316	0.072*
C18	0.73422 (12)	0.2233 (3)	0.53470 (12)	0.0729 (5)
H18	0.756	0.3185	0.5644	0.087*
C19	0.76854 (12)	0.0763 (3)	0.56945 (12)	0.0743 (5)
H19	0.813	0.0721	0.6229	0.089*
C20	0.73734 (12)	−0.0646 (3)	0.52550 (13)	0.0747 (5)
H20	0.7618	−0.1637	0.5489	0.09*
C21	0.66949 (11)	−0.0604 (2)	0.44627 (11)	0.0608 (4)
H21	0.6481	−0.1564	0.4172	0.073*
C22	0.63373 (9)	0.08832 (18)	0.41069 (9)	0.0469 (3)
C23	0.55780 (9)	0.09263 (18)	0.32620 (9)	0.0496 (4)
C24	0.57020 (11)	0.10567 (19)	0.25341 (10)	0.0539 (4)
C25	0.65069 (12)	0.1279 (2)	0.26229 (12)	0.0676 (5)
H25	0.6968	0.134	0.3147	0.081*
C26	0.66269 (15)	0.1409 (3)	0.19441 (15)	0.0808 (6)
H26	0.7163	0.156	0.2012	0.097*
C27	0.59361 (18)	0.1312 (3)	0.11627 (15)	0.0861 (7)
H27	0.6013	0.1387	0.0706	0.103*
C28	0.51399 (16)	0.1106 (2)	0.10547 (12)	0.0769 (6)
H28	0.4686	0.1045	0.0527	0.092*
C29	0.50056 (12)	0.09859 (19)	0.17301 (11)	0.0597 (4)
N1	0.23864 (8)	0.23289 (17)	0.28316 (8)	0.0562 (3)
N2	0.48206 (8)	0.08218 (17)	0.31467 (8)	0.0564 (3)
O1	0.18408 (8)	0.44387 (17)	0.34460 (7)	0.0709 (4)
H1A	0.2167	0.3781	0.3424	0.106*
O2	0.42130 (8)	0.08050 (17)	0.15964 (7)	0.0715 (4)
H2A	0.4218	0.074	0.2038	0.107*

	U11	U22	U33	U12	U13	U23
C1	0.0820 (13)	0.0800 (12)	0.0680 (11)	−0.0146 (10)	0.0478 (10)	−0.0153 (9)
C2	0.1009 (17)	0.125 (2)	0.0795 (14)	−0.0200 (15)	0.0625 (14)	−0.0331 (13)
C3	0.0776 (14)	0.1138 (19)	0.1001 (16)	−0.0262 (13)	0.0490 (13)	−0.0609 (14)
C4	0.0966 (17)	0.0856 (15)	0.1172 (18)	−0.0384 (13)	0.0610 (16)	−0.0465 (14)
C5	0.0807 (13)	0.0769 (12)	0.0816 (13)	−0.0279 (10)	0.0484 (11)	−0.0252 (10)
C6	0.0390 (7)	0.0596 (9)	0.0508 (8)	−0.0030 (6)	0.0212 (6)	−0.0107 (7)
C7	0.0393 (7)	0.0540 (8)	0.0465 (7)	−0.0056 (6)	0.0229 (6)	−0.0073 (6)
C8	0.0400 (7)	0.0531 (8)	0.0529 (8)	−0.0062 (6)	0.0250 (7)	−0.0070 (6)
C9	0.0456 (9)	0.0714 (11)	0.0615 (10)	−0.0002 (7)	0.0220 (8)	−0.0086 (8)
C10	0.0513 (10)	0.0855 (13)	0.0823 (13)	0.0124 (9)	0.0221 (9)	−0.0007 (11)
C11	0.0607 (12)	0.0732 (12)	0.1165 (18)	0.0144 (9)	0.0451 (13)	−0.0065 (12)
C12	0.0679 (12)	0.0709 (12)	0.0926 (14)	0.0000 (9)	0.0475 (11)	−0.0229 (10)
C13	0.0520 (9)	0.0573 (9)	0.0625 (10)	−0.0083 (7)	0.0338 (8)	−0.0127 (7)
C14	0.0450 (9)	0.0724 (11)	0.0627 (10)	0.0065 (7)	0.0175 (8)	−0.0136 (8)
C15	0.0442 (8)	0.0750 (11)	0.0546 (9)	−0.0015 (7)	0.0217 (7)	−0.0083 (8)
C16	0.0435 (8)	0.0848 (12)	0.0528 (9)	0.0052 (8)	0.0229 (7)	0.0092 (8)
C17	0.0553 (9)	0.0568 (9)	0.0662 (10)	−0.0005 (7)	0.0277 (8)	−0.0048 (8)
C18	0.0569 (10)	0.0913 (14)	0.0704 (12)	−0.0188 (10)	0.0310 (9)	−0.0281 (10)
C19	0.0501 (10)	0.1127 (17)	0.0548 (10)	0.0029 (10)	0.0213 (8)	0.0014 (10)
C20	0.0621 (11)	0.0852 (14)	0.0726 (12)	0.0204 (10)	0.0294 (10)	0.0230 (11)
C21	0.0566 (10)	0.0567 (9)	0.0669 (10)	0.0052 (7)	0.0282 (9)	0.0009 (8)
C22	0.0402 (7)	0.0523 (8)	0.0505 (8)	0.0024 (6)	0.0237 (7)	−0.0007 (6)
C23	0.0455 (8)	0.0508 (8)	0.0518 (8)	0.0035 (6)	0.0230 (7)	−0.0005 (6)
C24	0.0605 (9)	0.0511 (8)	0.0554 (9)	0.0042 (7)	0.0324 (8)	−0.0011 (7)
C25	0.0690 (11)	0.0714 (11)	0.0764 (12)	0.0021 (9)	0.0465 (10)	−0.0025 (9)
C26	0.0994 (16)	0.0749 (13)	0.1028 (16)	0.0019 (11)	0.0763 (15)	−0.0001 (11)
C27	0.136 (2)	0.0732 (13)	0.0831 (15)	0.0020 (13)	0.0797 (16)	0.0013 (11)
C28	0.1119 (17)	0.0633 (11)	0.0601 (11)	0.0001 (11)	0.0456 (12)	−0.0017 (8)
C29	0.0754 (12)	0.0501 (9)	0.0562 (9)	0.0028 (8)	0.0340 (9)	−0.0002 (7)
N1	0.0429 (7)	0.0685 (9)	0.0517 (7)	0.0042 (6)	0.0187 (6)	−0.0111 (6)
N2	0.0442 (7)	0.0732 (9)	0.0494 (7)	0.0036 (6)	0.0209 (6)	0.0030 (6)
O1	0.0677 (8)	0.0854 (9)	0.0572 (7)	0.0013 (6)	0.0285 (6)	−0.0219 (6)
O2	0.0667 (8)	0.0858 (9)	0.0505 (6)	−0.0029 (6)	0.0193 (6)	−0.0008 (6)

C1—C6	1.378 (2)	C15—H15B	0.97
C1—C2	1.396 (3)	C16—N2	1.469 (2)
C1—H1	0.93	C16—H16A	0.97
C2—C3	1.356 (3)	C16—H16B	0.97
C2—H2	0.93	C17—C22	1.391 (2)
C3—C4	1.358 (3)	C17—C18	1.393 (3)
C3—H3	0.93	C17—H17	0.93
C4—C5	1.394 (3)	C18—C19	1.371 (3)
C4—H4	0.93	C18—H18	0.93
C5—C6	1.385 (2)	C19—C20	1.374 (3)
C5—H5	0.93	C19—H19	0.93
C6—C7	1.507 (2)	C20—C21	1.392 (3)
C7—N1	1.2934 (19)	C20—H20	0.93
C7—C8	1.477 (2)	C21—C22	1.394 (2)
C8—C9	1.405 (2)	C21—H21	0.93
C8—C13	1.422 (2)	C22—C23	1.509 (2)
C9—C10	1.389 (3)	C23—N2	1.293 (2)
C9—H9	0.93	C23—C24	1.484 (2)
C10—C11	1.383 (3)	C24—C25	1.406 (2)
C10—H10	0.93	C24—C29	1.418 (2)
C11—C12	1.376 (3)	C25—C26	1.389 (3)
C11—H11	0.93	C25—H25	0.93
C12—C13	1.408 (2)	C26—C27	1.389 (3)
C12—H12	0.93	C26—H26	0.93
C13—O1	1.342 (2)	C27—C28	1.375 (3)
C14—N1	1.475 (2)	C27—H27	0.93
C14—C15	1.516 (2)	C28—C29	1.398 (3)
C14—H14A	0.97	C28—H28	0.93
C14—H14B	0.97	C29—O2	1.349 (2)
C15—C16	1.528 (2)	O1—H1A	0.82
C15—H15A	0.97	O2—H2A	0.82
C6—C1—C2	119.74 (19)	H15A—C15—H15B	107.7
C6—C1—H1	120.1	N2—C16—C15	110.13 (13)
C2—C1—H1	120.1	N2—C16—H16A	109.6
C3—C2—C1	120.5 (2)	C15—C16—H16A	109.6
C3—C2—H2	119.8	N2—C16—H16B	109.6
C1—C2—H2	119.8	C15—C16—H16B	109.6
C2—C3—C4	120.63 (19)	H16A—C16—H16B	108.1
C2—C3—H3	119.7	C22—C17—C18	120.06 (16)
C4—C3—H3	119.7	C22—C17—H17	120
C3—C4—C5	119.9 (2)	C18—C17—H17	120
C3—C4—H4	120.1	C19—C18—C17	120.31 (18)
C5—C4—H4	120.1	C19—C18—H18	119.8
C6—C5—C4	120.23 (19)	C17—C18—H18	119.8
C6—C5—H5	119.9	C18—C19—C20	120.11 (17)
C4—C5—H5	119.9	C18—C19—H19	119.9
C1—C6—C5	119.07 (16)	C20—C19—H19	119.9
C1—C6—C7	121.98 (15)	C19—C20—C21	120.55 (17)
C5—C6—C7	118.94 (15)	C19—C20—H20	119.7
N1—C7—C8	118.72 (13)	C21—C20—H20	119.7
N1—C7—C6	121.82 (13)	C20—C21—C22	119.74 (16)
C8—C7—C6	119.45 (12)	C20—C21—H21	120.1
C9—C8—C13	118.36 (14)	C22—C21—H21	120.1
C9—C8—C7	121.28 (13)	C17—C22—C21	119.22 (15)
C13—C8—C7	120.37 (13)	C17—C22—C23	120.95 (13)
C10—C9—C8	121.58 (17)	C21—C22—C23	119.78 (13)
C10—C9—H9	119.2	N2—C23—C24	118.54 (14)
C8—C9—H9	119.2	N2—C23—C22	122.36 (14)
C11—C10—C9	119.33 (19)	C24—C23—C22	119.09 (13)
C11—C10—H10	120.3	C25—C24—C29	118.44 (16)
C9—C10—H10	120.3	C25—C24—C23	121.04 (15)
C12—C11—C10	120.99 (17)	C29—C24—C23	120.51 (15)
C12—C11—H11	119.5	C26—C25—C24	121.34 (19)
C10—C11—H11	119.5	C26—C25—H25	119.3
C11—C12—C13	120.75 (17)	C24—C25—H25	119.3
C11—C12—H12	119.6	C27—C26—C25	119.15 (19)
C13—C12—H12	119.6	C27—C26—H26	120.4
O1—C13—C12	119.70 (15)	C25—C26—H26	120.4
O1—C13—C8	121.33 (14)	C28—C27—C26	120.96 (18)
C12—C13—C8	118.98 (16)	C28—C27—H27	119.5
N1—C14—C15	109.80 (14)	C26—C27—H27	119.5
N1—C14—H14A	109.7	C27—C28—C29	120.7 (2)
C15—C14—H14A	109.7	C27—C28—H28	119.6
N1—C14—H14B	109.7	C29—C28—H28	119.6
C15—C14—H14B	109.7	O2—C29—C28	118.80 (17)
H14A—C14—H14B	108.2	O2—C29—C24	121.83 (15)
C14—C15—C16	113.32 (14)	C28—C29—C24	119.37 (18)
C14—C15—H15A	108.9	C7—N1—C14	122.06 (13)
C16—C15—H15A	108.9	C23—N2—C16	122.40 (13)
C14—C15—H15B	108.9	C13—O1—H1A	109.5
C16—C15—H15B	108.9	C29—O2—H2A	109.5
C6—C1—C2—C3	0.8 (4)	C18—C19—C20—C21	−1.6 (3)
C1—C2—C3—C4	−0.1 (4)	C19—C20—C21—C22	1.0 (3)
C2—C3—C4—C5	−0.2 (4)	C18—C17—C22—C21	−1.1 (2)
C3—C4—C5—C6	−0.2 (4)	C18—C17—C22—C23	176.55 (14)
C2—C1—C6—C5	−1.2 (3)	C20—C21—C22—C17	0.3 (2)
C2—C1—C6—C7	177.65 (19)	C20—C21—C22—C23	−177.36 (15)
C4—C5—C6—C1	0.9 (3)	C17—C22—C23—N2	−90.01 (19)
C4—C5—C6—C7	−177.97 (19)	C21—C22—C23—N2	87.61 (19)
C1—C6—C7—N1	−96.1 (2)	C17—C22—C23—C24	91.38 (18)
C5—C6—C7—N1	82.8 (2)	C21—C22—C23—C24	−91.00 (18)
C1—C6—C7—C8	85.27 (19)	N2—C23—C24—C25	175.86 (15)
C5—C6—C7—C8	−95.88 (19)	C22—C23—C24—C25	−5.5 (2)
N1—C7—C8—C9	173.25 (15)	N2—C23—C24—C29	−3.1 (2)
C6—C7—C8—C9	−8.1 (2)	C22—C23—C24—C29	175.57 (13)
N1—C7—C8—C13	−6.6 (2)	C29—C24—C25—C26	−0.7 (3)
C6—C7—C8—C13	172.08 (13)	C23—C24—C25—C26	−179.70 (16)
C13—C8—C9—C10	1.0 (3)	C24—C25—C26—C27	−0.2 (3)
C7—C8—C9—C10	−178.90 (17)	C25—C26—C27—C28	0.7 (3)
C8—C9—C10—C11	−1.2 (3)	C26—C27—C28—C29	−0.1 (3)
C9—C10—C11—C12	0.5 (3)	C27—C28—C29—O2	179.16 (17)
C10—C11—C12—C13	0.4 (3)	C27—C28—C29—C24	−0.9 (3)
C11—C12—C13—O1	179.67 (18)	C25—C24—C29—O2	−178.77 (16)
C11—C12—C13—C8	−0.6 (3)	C23—C24—C29—O2	0.2 (2)
C9—C8—C13—O1	179.63 (15)	C25—C24—C29—C28	1.2 (2)
C7—C8—C13—O1	−0.5 (2)	C23—C24—C29—C28	−179.77 (15)
C9—C8—C13—C12	−0.1 (2)	C8—C7—N1—C14	−176.84 (14)
C7—C8—C13—C12	179.80 (15)	C6—C7—N1—C14	4.5 (2)
N1—C14—C15—C16	−176.82 (14)	C15—C14—N1—C7	155.47 (15)
C14—C15—C16—N2	70.2 (2)	C24—C23—N2—C16	−179.47 (14)
C22—C17—C18—C19	0.5 (3)	C22—C23—N2—C16	1.9 (2)
C17—C18—C19—C20	0.8 (3)	C15—C16—N2—C23	137.49 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.80	2.5344 (17)	148
O2—H2A···N2	0.82	1.81	2.5431 (18)	148
C17—H17···O2i	0.93	2.56	3.481 (2)	168
C18—H18···O1ii	0.93	2.47	3.395 (3)	174
C21—H21···O2iii	0.93	2.56	3.492 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.80	2.5344 (17)	148
O2—H2A⋯N2	0.82	1.81	2.5431 (18)	148
C17—H17⋯O2i	0.93	2.56	3.481 (2)	168
C18—H18⋯O1ii	0.93	2.47	3.395 (3)	174
C21—H21⋯O2iii	0.93	2.56	3.492 (2)	175

Symmetry codes: (i) ; (ii) ; (iii) .