N,N'-Bis[(2-hydroxy-phen-yl)(phen-yl)methyl-idene]propane-1,2-diamine.

In the the title compound, C(29)H(26)N(2)O(2), two strong intra-molecular O-H⋯N hydrogen bonds involving the hydr-oxy and imine groups generate S(6) ring motifs. The dihedral angles between the pairs of terminal benzene rings are 89.8 (2) and 87.8 (2)°.

Related literature

For related compounds and further synthetic details, see: Schilf et al. (2007 ▶). For intra­molecular hydrogen bonds in this type of compound, see: Fernández-G 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 ▶); Black et al. (2010 ▶); Dey et al. (2001 ▶).

Experimental

Crystal data

C29H26N2O2

M = 434.52

Monoclinic,

a = 18.1766 (8) Å

b = 7.9808 (4) Å

c = 16.0347 (8) Å

β = 92.703 (2)°

V = 2323.47 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.62 × 0.38 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: integration (XPREP; Bruker, 1999 ▶) T min = 0.918, T max = 1.000

22291 measured reflections

3001 independent reflections

2724 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.05

3001 reflections

301 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (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/S1600536810015291/hb5392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015291/hb5392Isup2.hkl

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

C29H26N2O2	F(000) = 920
Mr = 434.52	Dx = 1.242 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 9931 reflections
a = 18.1766 (8) Å	θ = 2.2–28.3°
b = 7.9808 (4) Å	µ = 0.08 mm−1
c = 16.0347 (8) Å	T = 296 K
β = 92.703 (2)°	Block, yellow
V = 2323.47 (19) Å3	0.62 × 0.38 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	3001 independent reflections
Radiation source: sealed tube	2724 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28°, θmin = 1.3°
Absorption correction: integration (XPREP; Bruker, 1999)	h = −23→24
Tmin = 0.918, Tmax = 1.000	k = −10→10
22291 measured reflections	l = −21→20

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6417P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.20 e Å−3
3001 reflections	Δρmin = −0.18 e Å−3
301 parameters

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999)

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	0.17117 (10)	0.8773 (3)	0.19104 (12)	0.0380 (4)
H1	0.1576	0.8561	0.2453	0.046*
C2	0.23795 (11)	0.9528 (3)	0.17780 (14)	0.0452 (5)
H2	0.2699	0.9792	0.2229	0.054*
C3	0.25725 (11)	0.9890 (3)	0.09795 (15)	0.0500 (5)
H3	0.302	1.0411	0.0891	0.06*
C4	0.21054 (12)	0.9484 (3)	0.03135 (14)	0.0536 (5)
H4	0.2237	0.974	−0.0225	0.064*
C5	0.14368 (11)	0.8693 (3)	0.04351 (12)	0.0432 (5)
H5	0.1124	0.8412	−0.0019	0.052*
C6	0.12418 (9)	0.8328 (2)	0.12419 (11)	0.0318 (4)
C7	0.05455 (9)	0.7387 (2)	0.14143 (10)	0.0308 (4)
C8	−0.01204 (10)	0.8365 (2)	0.15614 (11)	0.0317 (4)
C9	−0.01477 (11)	1.0091 (2)	0.14096 (13)	0.0398 (4)
H9	0.0267	1.0624	0.1219	0.048*
C10	−0.07704 (12)	1.1025 (3)	0.15342 (13)	0.0478 (5)
H10	−0.0777	1.2167	0.142	0.057*
C11	−0.13872 (12)	1.0242 (3)	0.18322 (14)	0.0487 (5)
H11	−0.1808	1.0867	0.1924	0.058*
C12	−0.13812 (11)	0.8549 (3)	0.19929 (13)	0.0445 (5)
H12	−0.1796	0.8042	0.2199	0.053*
C13	−0.07625 (10)	0.7587 (3)	0.18505 (12)	0.0372 (4)
C14	0.09851 (12)	0.3771 (3)	0.04854 (12)	0.0445 (5)
H14A	0.0548	0.3114	0.0545	0.067*
H14B	0.139	0.3044	0.0374	0.067*
H14C	0.0907	0.4544	0.0031	0.067*
C15	0.11599 (10)	0.4740 (2)	0.12901 (11)	0.0330 (4)
H15	0.1592	0.5453	0.1221	0.04*
C16	0.13115 (11)	0.3541 (2)	0.20186 (11)	0.0364 (4)
H16A	0.0869	0.2909	0.2124	0.044*
H16B	0.1695	0.2755	0.1882	0.044*
C17	−0.00368 (11)	0.3145 (3)	0.35288 (13)	0.0447 (5)
H17	−0.0215	0.4205	0.3389	0.054*
C18	−0.05238 (12)	0.1829 (4)	0.36563 (14)	0.0602 (7)
H18	−0.1029	0.2012	0.3604	0.072*
C19	−0.02579 (16)	0.0266 (4)	0.38587 (16)	0.0640 (7)
H19	−0.0585	−0.0607	0.3944	0.077*
C20	0.04851 (16)	−0.0019 (3)	0.39361 (17)	0.0639 (7)
H20	0.066	−0.1085	0.4071	0.077*
C21	0.09762 (13)	0.1270 (3)	0.38147 (14)	0.0477 (5)
H21	0.148	0.1073	0.3869	0.057*
C22	0.07149 (10)	0.2860 (2)	0.36114 (11)	0.0331 (4)
C23	0.12560 (9)	0.4238 (2)	0.34679 (11)	0.0307 (3)
C24	0.14855 (9)	0.5331 (2)	0.41770 (11)	0.0304 (3)
C25	0.11331 (10)	0.5252 (2)	0.49331 (12)	0.0368 (4)
H25	0.0749	0.4495	0.4988	0.044*
C26	0.13414 (11)	0.6270 (3)	0.56007 (13)	0.0437 (5)
H26	0.1102	0.6195	0.6099	0.052*
C27	0.19109 (12)	0.7405 (3)	0.55188 (14)	0.0477 (5)
H27	0.2049	0.8105	0.5963	0.057*
C28	0.22735 (11)	0.7505 (3)	0.47865 (13)	0.0461 (5)
H28	0.2658	0.8264	0.4741	0.055*
C29	0.20693 (9)	0.6482 (2)	0.41146 (11)	0.0355 (4)
N1	0.05252 (8)	0.57835 (19)	0.14636 (9)	0.0338 (3)
N2	0.15442 (8)	0.44924 (19)	0.27629 (9)	0.0348 (3)
O1	−0.07848 (8)	0.59298 (19)	0.20016 (11)	0.0509 (4)
H1A	−0.0408	0.5489	0.1844	0.076*
O2	0.24508 (8)	0.6613 (2)	0.34177 (8)	0.0487 (4)
H2A	0.2264	0.6006	0.3053	0.073*

	U11	U22	U33	U12	U13	U23
C1	0.0384 (10)	0.0346 (9)	0.0407 (9)	−0.0049 (8)	0.0003 (8)	−0.0001 (8)
C2	0.0365 (10)	0.0390 (10)	0.0591 (12)	−0.0070 (8)	−0.0073 (8)	−0.0052 (9)
C3	0.0296 (10)	0.0468 (12)	0.0742 (14)	−0.0096 (9)	0.0104 (9)	−0.0005 (11)
C4	0.0464 (11)	0.0669 (14)	0.0487 (11)	−0.0111 (11)	0.0144 (9)	0.0084 (11)
C5	0.0386 (10)	0.0536 (12)	0.0374 (9)	−0.0087 (9)	0.0009 (8)	0.0026 (9)
C6	0.0301 (9)	0.0270 (8)	0.0383 (9)	−0.0033 (7)	0.0021 (7)	0.0017 (7)
C7	0.0299 (8)	0.0341 (9)	0.0280 (8)	−0.0069 (7)	−0.0017 (6)	0.0013 (6)
C8	0.0303 (9)	0.0335 (9)	0.0311 (8)	−0.0046 (7)	−0.0011 (6)	−0.0007 (7)
C9	0.0379 (10)	0.0355 (10)	0.0462 (10)	−0.0049 (8)	0.0031 (8)	−0.0008 (8)
C10	0.0544 (12)	0.0365 (10)	0.0526 (12)	0.0058 (9)	0.0034 (10)	−0.0034 (9)
C11	0.0418 (11)	0.0531 (13)	0.0513 (12)	0.0102 (10)	0.0028 (9)	−0.0072 (10)
C12	0.0310 (10)	0.0535 (13)	0.0494 (11)	−0.0034 (9)	0.0057 (8)	0.0002 (9)
C13	0.0315 (9)	0.0409 (10)	0.0389 (9)	−0.0042 (8)	−0.0020 (7)	0.0016 (8)
C14	0.0513 (12)	0.0435 (10)	0.0391 (9)	−0.0056 (10)	0.0053 (8)	−0.0027 (9)
C15	0.0318 (9)	0.0306 (9)	0.0372 (9)	−0.0056 (7)	0.0066 (7)	−0.0007 (7)
C16	0.0406 (10)	0.0294 (8)	0.0391 (9)	−0.0029 (7)	0.0018 (7)	−0.0018 (7)
C17	0.0341 (9)	0.0512 (12)	0.0492 (11)	−0.0046 (9)	0.0052 (8)	−0.0058 (9)
C18	0.0379 (11)	0.089 (2)	0.0546 (13)	−0.0233 (12)	0.0085 (9)	−0.0164 (13)
C19	0.0761 (18)	0.0632 (16)	0.0534 (13)	−0.0401 (15)	0.0107 (12)	−0.0014 (12)
C20	0.0856 (19)	0.0415 (12)	0.0645 (15)	−0.0188 (13)	0.0017 (13)	0.0086 (11)
C21	0.0495 (12)	0.0368 (10)	0.0564 (12)	−0.0059 (9)	−0.0017 (9)	0.0050 (9)
C22	0.0328 (9)	0.0340 (9)	0.0326 (8)	−0.0063 (7)	0.0012 (7)	−0.0034 (7)
C23	0.0263 (8)	0.0258 (8)	0.0396 (9)	0.0011 (6)	−0.0013 (6)	0.0008 (7)
C24	0.0260 (8)	0.0266 (8)	0.0382 (8)	0.0013 (6)	−0.0028 (6)	0.0002 (7)
C25	0.0309 (9)	0.0336 (9)	0.0461 (10)	−0.0024 (8)	0.0034 (7)	−0.0017 (8)
C26	0.0419 (10)	0.0466 (11)	0.0429 (10)	−0.0020 (9)	0.0067 (8)	−0.0078 (8)
C27	0.0472 (11)	0.0480 (12)	0.0473 (11)	−0.0063 (10)	−0.0032 (9)	−0.0140 (9)
C28	0.0404 (10)	0.0452 (11)	0.0520 (11)	−0.0149 (9)	−0.0066 (8)	−0.0033 (9)
C29	0.0307 (9)	0.0357 (9)	0.0398 (9)	−0.0026 (8)	−0.0029 (7)	0.0036 (8)
N1	0.0307 (7)	0.0322 (8)	0.0385 (8)	−0.0061 (6)	0.0031 (6)	0.0001 (6)
N2	0.0345 (7)	0.0323 (7)	0.0376 (7)	−0.0043 (6)	0.0003 (6)	−0.0011 (6)
O1	0.0343 (7)	0.0413 (8)	0.0778 (11)	−0.0062 (6)	0.0092 (7)	0.0116 (8)
O2	0.0440 (8)	0.0613 (10)	0.0410 (7)	−0.0221 (7)	0.0020 (6)	0.0007 (7)

C1—C2	1.380 (3)	C15—H15	0.98
C1—C6	1.385 (3)	C16—N2	1.460 (2)
C1—H1	0.93	C16—H16A	0.97
C2—C3	1.374 (3)	C16—H16B	0.97
C2—H2	0.93	C17—C22	1.385 (3)
C3—C4	1.371 (3)	C17—C18	1.395 (3)
C3—H3	0.93	C17—H17	0.93
C4—C5	1.391 (3)	C18—C19	1.372 (4)
C4—H4	0.93	C18—H18	0.93
C5—C6	1.388 (3)	C19—C20	1.369 (4)
C5—H5	0.93	C19—H19	0.93
C6—C7	1.508 (2)	C20—C21	1.382 (3)
C7—N1	1.283 (2)	C20—H20	0.93
C7—C8	1.469 (3)	C21—C22	1.389 (3)
C8—C9	1.399 (3)	C21—H21	0.93
C8—C13	1.419 (2)	C22—C23	1.500 (2)
C9—C10	1.378 (3)	C23—N2	1.284 (2)
C9—H9	0.93	C23—C24	1.477 (2)
C10—C11	1.388 (3)	C24—C25	1.399 (2)
C10—H10	0.93	C24—C29	1.411 (2)
C11—C12	1.376 (3)	C25—C26	1.383 (3)
C11—H11	0.93	C25—H25	0.93
C12—C13	1.389 (3)	C26—C27	1.386 (3)
C12—H12	0.93	C26—H26	0.93
C13—O1	1.346 (3)	C27—C28	1.376 (3)
C14—C15	1.525 (3)	C27—H27	0.93
C14—H14A	0.96	C28—C29	1.388 (3)
C14—H14B	0.96	C28—H28	0.93
C14—H14C	0.96	C29—O2	1.347 (2)
C15—N1	1.460 (2)	O1—H1A	0.82
C15—C16	1.525 (3)	O2—H2A	0.82
C2—C1—C6	120.49 (18)	C16—C15—H15	109.5
C2—C1—H1	119.8	N2—C16—C15	109.55 (15)
C6—C1—H1	119.8	N2—C16—H16A	109.8
C3—C2—C1	120.01 (18)	C15—C16—H16A	109.8
C3—C2—H2	120	N2—C16—H16B	109.8
C1—C2—H2	120	C15—C16—H16B	109.8
C4—C3—C2	120.00 (18)	H16A—C16—H16B	108.2
C4—C3—H3	120	C22—C17—C18	119.5 (2)
C2—C3—H3	120	C22—C17—H17	120.2
C3—C4—C5	120.72 (19)	C18—C17—H17	120.2
C3—C4—H4	119.6	C19—C18—C17	120.0 (2)
C5—C4—H4	119.6	C19—C18—H18	120
C6—C5—C4	119.26 (18)	C17—C18—H18	120
C6—C5—H5	120.4	C20—C19—C18	120.5 (2)
C4—C5—H5	120.4	C20—C19—H19	119.7
C1—C6—C5	119.48 (17)	C18—C19—H19	119.7
C1—C6—C7	118.56 (16)	C19—C20—C21	120.3 (2)
C5—C6—C7	121.90 (16)	C19—C20—H20	119.9
N1—C7—C8	119.60 (16)	C21—C20—H20	119.9
N1—C7—C6	122.34 (17)	C20—C21—C22	119.8 (2)
C8—C7—C6	118.02 (15)	C20—C21—H21	120.1
C9—C8—C13	117.66 (17)	C22—C21—H21	120.1
C9—C8—C7	121.20 (17)	C17—C22—C21	119.81 (18)
C13—C8—C7	121.13 (15)	C17—C22—C23	121.07 (18)
C10—C9—C8	122.01 (19)	C21—C22—C23	119.12 (16)
C10—C9—H9	119	N2—C23—C24	118.18 (15)
C8—C9—H9	119	N2—C23—C22	123.25 (16)
C9—C10—C11	119.3 (2)	C24—C23—C22	118.55 (15)
C9—C10—H10	120.4	C25—C24—C29	117.87 (16)
C11—C10—H10	120.4	C25—C24—C23	121.07 (15)
C12—C11—C10	120.5 (2)	C29—C24—C23	121.06 (15)
C12—C11—H11	119.8	C26—C25—C24	121.64 (18)
C10—C11—H11	119.8	C26—C25—H25	119.2
C11—C12—C13	120.7 (2)	C24—C25—H25	119.2
C11—C12—H12	119.6	C25—C26—C27	119.29 (19)
C13—C12—H12	119.6	C25—C26—H26	120.4
O1—C13—C12	118.80 (18)	C27—C26—H26	120.4
O1—C13—C8	121.39 (17)	C28—C27—C26	120.58 (19)
C12—C13—C8	119.81 (18)	C28—C27—H27	119.7
C15—C14—H14A	109.5	C26—C27—H27	119.7
C15—C14—H14B	109.5	C27—C28—C29	120.45 (19)
H14A—C14—H14B	109.5	C27—C28—H28	119.8
C15—C14—H14C	109.5	C29—C28—H28	119.8
H14A—C14—H14C	109.5	O2—C29—C28	117.95 (17)
H14B—C14—H14C	109.5	O2—C29—C24	121.87 (16)
N1—C15—C14	108.39 (15)	C28—C29—C24	120.17 (17)
N1—C15—C16	109.14 (14)	C7—N1—C15	122.13 (16)
C14—C15—C16	110.66 (15)	C23—N2—C16	121.53 (16)
N1—C15—H15	109.5	C13—O1—H1A	109.5
C14—C15—H15	109.5	C29—O2—H2A	109.5
C6—C1—C2—C3	2.0 (3)	C19—C20—C21—C22	−0.1 (4)
C1—C2—C3—C4	−0.7 (3)	C18—C17—C22—C21	0.4 (3)
C2—C3—C4—C5	−0.5 (4)	C18—C17—C22—C23	179.17 (18)
C3—C4—C5—C6	0.5 (4)	C20—C21—C22—C17	−0.2 (3)
C2—C1—C6—C5	−1.9 (3)	C20—C21—C22—C23	−179.00 (19)
C2—C1—C6—C7	175.34 (18)	C17—C22—C23—N2	−93.9 (2)
C4—C5—C6—C1	0.7 (3)	C21—C22—C23—N2	84.9 (2)
C4—C5—C6—C7	−176.5 (2)	C17—C22—C23—C24	87.8 (2)
C1—C6—C7—N1	−87.8 (2)	C21—C22—C23—C24	−93.4 (2)
C5—C6—C7—N1	89.5 (2)	N2—C23—C24—C25	172.54 (17)
C1—C6—C7—C8	89.8 (2)	C22—C23—C24—C25	−9.1 (2)
C5—C6—C7—C8	−92.9 (2)	N2—C23—C24—C29	−7.8 (2)
N1—C7—C8—C9	−171.73 (18)	C22—C23—C24—C29	170.61 (16)
C6—C7—C8—C9	10.6 (2)	C29—C24—C25—C26	0.5 (3)
N1—C7—C8—C13	7.3 (3)	C23—C24—C25—C26	−179.84 (18)
C6—C7—C8—C13	−170.35 (16)	C24—C25—C26—C27	0.3 (3)
C13—C8—C9—C10	0.1 (3)	C25—C26—C27—C28	−0.9 (3)
C7—C8—C9—C10	179.19 (17)	C26—C27—C28—C29	0.7 (3)
C8—C9—C10—C11	1.1 (3)	C27—C28—C29—O2	−178.9 (2)
C9—C10—C11—C12	−0.7 (3)	C27—C28—C29—C24	0.2 (3)
C10—C11—C12—C13	−0.8 (3)	C25—C24—C29—O2	178.35 (17)
C11—C12—C13—O1	−178.8 (2)	C23—C24—C29—O2	−1.4 (3)
C11—C12—C13—C8	2.0 (3)	C25—C24—C29—C28	−0.7 (3)
C9—C8—C13—O1	179.18 (19)	C23—C24—C29—C28	179.59 (17)
C7—C8—C13—O1	0.1 (3)	C8—C7—N1—C15	177.40 (14)
C9—C8—C13—C12	−1.7 (3)	C6—C7—N1—C15	−5.0 (3)
C7—C8—C13—C12	179.27 (17)	C14—C15—N1—C7	−111.3 (2)
N1—C15—C16—N2	−66.08 (18)	C16—C15—N1—C7	128.14 (18)
C14—C15—C16—N2	174.74 (15)	C24—C23—N2—C16	−175.93 (15)
C22—C17—C18—C19	−0.2 (3)	C22—C23—N2—C16	5.8 (3)
C17—C18—C19—C20	−0.1 (4)	C15—C16—N2—C23	131.47 (17)
C18—C19—C20—C21	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.84	2.573 (2)	147
O2—H2A···N2	0.82	1.83	2.553 (2)	147

Table 1

Selected torsion angles (°)

C1—C6—C7—C8	89.8 (2)
C17—C22—C23—C24	87.8 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.84	2.573 (2)	147
O2—H2A⋯N2	0.82	1.83	2.553 (2)	147