2-((E)-{4-[Bis(4-eth-oxy-phen-yl)amino]-phen-yl}imino-meth-yl)phenol.

In the title Schiff base mol-ecule, C29H28N2O3, the three terminal benzene rings are twisted by 73.84 (15), 81.25 (16) and 12.1 (2)° with respect to the central benzene ring. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, mol-ecules are linked via weak C-H⋯π inter-actions into a three-dimensional supra-molecular architecture.

Related literature

For background and the synthesis of the title compound, see: Dharmaraj et al. (2001 ▶); Feng (2014 ▶). For a related structure, see: Tanak et al. (2013 ▶).

Experimental

Crystal data

C29H28N2O3

M = 452.53

Orthorhombic,

a = 9.765 (3) Å

b = 13.113 (4) Å

c = 19.378 (6) Å

V = 2481.2 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.969, T max = 0.984

17684 measured reflections

2486 independent reflections

1747 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.13

2486 reflections

310 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814003201/xu5765sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003201/xu5765Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003201/xu5765Isup3.cml

CCDC reference: 986499

Additional supporting information: crystallographic information; 3D view; checkCIF report

C29H28N2O3	Dx = 1.211 Mg m−3
Mr = 452.53	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2336 reflections
a = 9.765 (3) Å	θ = 2.3–20.7°
b = 13.113 (4) Å	µ = 0.08 mm−1
c = 19.378 (6) Å	T = 296 K
V = 2481.2 (14) Å3	Block, yellow
Z = 4	0.40 × 0.30 × 0.20 mm
F(000) = 960

Bruker SMART CCD area-detector diffractometer	2486 independent reflections
Radiation source: fine-focus sealed tube	1747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
phi and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.969, Tmax = 0.984	k = −15→15
17684 measured reflections	l = −22→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3
2486 reflections	(Δ/σ)max < 0.001
310 parameters	Δρmax = 0.12 e Å−3
6 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1807 (5)	0.6157 (3)	1.2427 (2)	0.0891 (13)
H1A	0.1266	0.6695	1.2231	0.134*
H1B	0.2698	0.6414	1.2543	0.134*
H1C	0.1367	0.5904	1.2835	0.134*
C2	0.1945 (4)	0.5321 (3)	1.1919 (2)	0.0741 (11)
H2A	0.2332	0.5582	1.1493	0.089*
H2B	0.2555	0.4800	1.2098	0.089*
C3	0.0558 (3)	0.4027 (2)	1.13890 (15)	0.0476 (8)
C4	0.1641 (3)	0.3628 (2)	1.10191 (16)	0.0554 (9)
H4	0.2488	0.3953	1.1023	0.066*
C5	0.1461 (3)	0.2750 (3)	1.06451 (17)	0.0569 (9)
H5	0.2196	0.2478	1.0402	0.068*
C6	0.0203 (3)	0.2259 (2)	1.06227 (15)	0.0484 (8)
C7	−0.0875 (3)	0.2676 (3)	1.09885 (16)	0.0560 (9)
H7	−0.1727	0.2361	1.0976	0.067*
C8	−0.0708 (4)	0.3548 (2)	1.13691 (16)	0.0551 (9)
H8	−0.1442	0.3819	1.1614	0.066*
C9	−0.2070 (4)	−0.3382 (3)	1.25128 (19)	0.0800 (12)
H9A	−0.1536	−0.3916	1.2306	0.120*
H9B	−0.2961	−0.3639	1.2629	0.120*
H9C	−0.1621	−0.3145	1.2923	0.120*
C10	−0.2213 (4)	−0.2511 (3)	1.2010 (2)	0.0757 (11)
H10A	−0.2586	−0.2754	1.1576	0.091*
H10B	−0.2823	−0.1995	1.2195	0.091*
C11	−0.0768 (4)	−0.1254 (2)	1.14919 (16)	0.0546 (8)
C12	0.0506 (4)	−0.0825 (3)	1.14815 (18)	0.0648 (10)
H12	0.1200	−0.1098	1.1753	0.078*
C13	0.0772 (4)	0.0010 (3)	1.10721 (17)	0.0584 (9)
H13	0.1647	0.0290	1.1063	0.070*
C14	−0.0254 (4)	0.0431 (2)	1.06752 (16)	0.0513 (8)
C15	−0.1533 (4)	0.0009 (3)	1.06924 (18)	0.0613 (9)
H15	−0.2233	0.0293	1.0430	0.074*
C16	−0.1797 (3)	−0.0843 (3)	1.11010 (18)	0.0631 (10)
H16	−0.2667	−0.1132	1.1108	0.076*
C17	0.0234 (3)	0.1219 (2)	0.95562 (15)	0.0486 (8)
C18	0.0227 (3)	0.2085 (2)	0.91266 (15)	0.0494 (8)
H18	0.0144	0.2732	0.9318	0.059*
C19	0.0345 (3)	0.1973 (2)	0.84202 (16)	0.0524 (8)
H19	0.0340	0.2552	0.8142	0.063*
C20	0.0470 (3)	0.1022 (2)	0.81143 (15)	0.0483 (8)
C21	0.0489 (4)	0.0180 (2)	0.85418 (17)	0.0556 (9)
H21	0.0576	−0.0465	0.8348	0.067*
C22	0.0384 (4)	0.0268 (2)	0.92461 (16)	0.0562 (9)
H22	0.0413	−0.0314	0.9519	0.067*
N2	0.0527 (3)	0.0833 (2)	0.73886 (13)	0.0539 (7)
C24	0.0683 (4)	0.1357 (3)	0.62156 (17)	0.0636 (9)
C25	0.0822 (7)	0.2158 (4)	0.5769 (2)	0.129 (2)
H25	0.0939	0.2812	0.5944	0.154*
C26	0.0793 (8)	0.2014 (4)	0.5064 (2)	0.146 (2)
H26	0.0878	0.2568	0.4767	0.175*
C27	0.0637 (7)	0.1046 (4)	0.4803 (2)	0.125 (2)
H27	0.0633	0.0945	0.4328	0.150*
C28	0.0490 (5)	0.0243 (3)	0.52299 (19)	0.0818 (12)
H28	0.0381	−0.0409	0.5050	0.098*
C29	0.0503 (4)	0.0392 (3)	0.59391 (17)	0.0615 (9)
N1	0.0028 (3)	0.13169 (19)	1.02609 (13)	0.0572 (8)
C23	0.0688 (4)	0.1534 (3)	0.69541 (17)	0.0633 (9)
H23	0.0816	0.2197	0.7113	0.076*
O1	−0.0896 (3)	−0.21002 (19)	1.19072 (13)	0.0745 (7)
O2	0.0625 (2)	0.48898 (16)	1.17876 (11)	0.0613 (6)
O3	0.0333 (4)	−0.04181 (18)	0.63487 (13)	0.0933 (10)
H3	0.0383	−0.0239	0.6753	0.140*

	U11	U22	U33	U12	U13	U23
C1	0.095 (3)	0.078 (3)	0.093 (3)	−0.022 (2)	0.003 (3)	−0.023 (3)
C2	0.069 (3)	0.069 (2)	0.085 (3)	−0.015 (2)	0.005 (2)	−0.012 (2)
C3	0.053 (2)	0.0494 (19)	0.0401 (17)	0.0010 (16)	0.0005 (15)	−0.0007 (15)
C4	0.0502 (18)	0.062 (2)	0.054 (2)	−0.0089 (17)	0.0027 (17)	−0.0064 (19)
C5	0.053 (2)	0.065 (2)	0.0527 (19)	−0.0001 (18)	0.0150 (17)	−0.0058 (18)
C6	0.058 (2)	0.0510 (19)	0.0365 (16)	−0.0029 (17)	0.0009 (15)	0.0031 (15)
C7	0.0462 (19)	0.067 (2)	0.0550 (19)	−0.0081 (17)	0.0033 (16)	0.0012 (19)
C8	0.049 (2)	0.064 (2)	0.052 (2)	0.0052 (17)	0.0050 (16)	−0.0077 (18)
C9	0.097 (3)	0.072 (3)	0.071 (2)	−0.023 (2)	0.002 (2)	0.014 (2)
C10	0.073 (3)	0.072 (2)	0.082 (3)	−0.010 (2)	0.002 (2)	0.008 (2)
C11	0.068 (2)	0.0469 (19)	0.0492 (18)	0.0013 (18)	0.0059 (18)	0.0055 (17)
C12	0.061 (2)	0.067 (2)	0.067 (2)	0.002 (2)	−0.0060 (19)	0.012 (2)
C13	0.054 (2)	0.061 (2)	0.060 (2)	−0.0035 (17)	0.0025 (18)	0.0040 (19)
C14	0.060 (2)	0.0538 (19)	0.0398 (17)	−0.0022 (17)	0.0059 (16)	−0.0005 (16)
C15	0.063 (2)	0.059 (2)	0.062 (2)	−0.0035 (19)	−0.0084 (18)	0.0085 (19)
C16	0.053 (2)	0.063 (2)	0.073 (2)	−0.0079 (18)	0.000 (2)	0.007 (2)
C17	0.0502 (19)	0.056 (2)	0.0397 (17)	−0.0035 (17)	0.0018 (14)	−0.0008 (16)
C18	0.054 (2)	0.0496 (18)	0.0443 (18)	−0.0055 (16)	−0.0008 (15)	−0.0019 (15)
C19	0.055 (2)	0.0566 (19)	0.0460 (18)	−0.0032 (17)	0.0010 (17)	0.0040 (16)
C20	0.0463 (19)	0.059 (2)	0.0395 (16)	0.0027 (17)	−0.0015 (15)	−0.0018 (16)
C21	0.070 (2)	0.0464 (18)	0.0508 (19)	0.0026 (18)	0.0012 (18)	−0.0051 (16)
C22	0.072 (2)	0.0481 (19)	0.0479 (19)	0.0053 (18)	0.0019 (18)	0.0021 (16)
N2	0.0578 (17)	0.0597 (17)	0.0440 (15)	0.0038 (14)	0.0024 (14)	0.0000 (15)
C24	0.081 (2)	0.065 (2)	0.0452 (19)	−0.015 (2)	0.0012 (19)	0.0000 (19)
C25	0.233 (7)	0.091 (3)	0.061 (3)	−0.055 (4)	0.010 (4)	0.006 (3)
C26	0.259 (7)	0.115 (4)	0.063 (3)	−0.054 (4)	0.009 (4)	0.019 (3)
C27	0.208 (6)	0.123 (4)	0.044 (2)	−0.050 (4)	0.001 (3)	−0.006 (3)
C28	0.112 (3)	0.083 (3)	0.051 (2)	−0.011 (3)	−0.009 (2)	−0.007 (2)
C29	0.067 (2)	0.067 (2)	0.051 (2)	0.001 (2)	−0.0048 (19)	0.002 (2)
N1	0.085 (2)	0.0491 (16)	0.0381 (14)	−0.0123 (15)	0.0043 (14)	−0.0009 (13)
C23	0.076 (2)	0.060 (2)	0.053 (2)	−0.014 (2)	0.005 (2)	−0.0069 (19)
O1	0.0706 (17)	0.0684 (15)	0.0846 (17)	−0.0048 (14)	0.0022 (14)	0.0202 (14)
O2	0.0602 (15)	0.0605 (14)	0.0630 (15)	−0.0050 (12)	0.0041 (12)	−0.0160 (12)
O3	0.159 (3)	0.0601 (16)	0.0610 (16)	0.0017 (19)	−0.008 (2)	−0.0043 (14)

C1—C2	1.479 (5)	C14—C15	1.367 (5)
C1—H1A	0.9600	C14—N1	1.439 (4)
C1—H1B	0.9600	C15—C16	1.394 (4)
C1—H1C	0.9600	C15—H15	0.9300
C2—O2	1.431 (4)	C16—H16	0.9300
C2—H2A	0.9700	C17—N1	1.386 (4)
C2—H2B	0.9700	C17—C22	1.392 (4)
C3—O2	1.371 (3)	C17—C18	1.407 (4)
C3—C4	1.380 (4)	C18—C19	1.381 (4)
C3—C8	1.387 (5)	C18—H18	0.9300
C4—C5	1.372 (4)	C19—C20	1.387 (4)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.388 (4)	C20—C21	1.380 (4)
C5—H5	0.9300	C20—N2	1.429 (4)
C6—C7	1.382 (4)	C21—C22	1.373 (4)
C6—N1	1.431 (4)	C21—H21	0.9300
C7—C8	1.370 (4)	C22—H22	0.9300
C7—H7	0.9300	N2—C23	1.257 (4)
C8—H8	0.9300	C24—C25	1.368 (5)
C9—C10	1.508 (5)	C24—C29	1.385 (5)
C9—H9A	0.9600	C24—C23	1.450 (5)
C9—H9B	0.9600	C25—C26	1.379 (6)
C9—H9C	0.9600	C25—H25	0.9300
C10—O1	1.408 (4)	C26—C27	1.375 (6)
C10—H10A	0.9700	C26—H26	0.9300
C10—H10B	0.9700	C27—C28	1.347 (6)
C11—C12	1.366 (5)	C27—H27	0.9300
C11—C16	1.369 (5)	C28—C29	1.388 (5)
C11—O1	1.376 (4)	C28—H28	0.9300
C12—C13	1.376 (5)	C29—O3	1.337 (4)
C12—H12	0.9300	C23—H23	0.9300
C13—C14	1.379 (4)	O3—H3	0.8200
C13—H13	0.9300
C2—C1—H1A	109.5	C13—C14—N1	119.8 (3)
C2—C1—H1B	109.5	C14—C15—C16	120.5 (3)
H1A—C1—H1B	109.5	C14—C15—H15	119.7
C2—C1—H1C	109.5	C16—C15—H15	119.7
H1A—C1—H1C	109.5	C11—C16—C15	119.6 (3)
H1B—C1—H1C	109.5	C11—C16—H16	120.2
O2—C2—C1	109.2 (3)	C15—C16—H16	120.2
O2—C2—H2A	109.8	N1—C17—C22	121.5 (3)
C1—C2—H2A	109.8	N1—C17—C18	120.5 (3)
O2—C2—H2B	109.8	C22—C17—C18	117.9 (3)
C1—C2—H2B	109.8	C19—C18—C17	120.0 (3)
H2A—C2—H2B	108.3	C19—C18—H18	120.0
O2—C3—C4	124.7 (3)	C17—C18—H18	120.0
O2—C3—C8	115.6 (3)	C18—C19—C20	121.7 (3)
C4—C3—C8	119.8 (3)	C18—C19—H19	119.1
C5—C4—C3	119.6 (3)	C20—C19—H19	119.1
C5—C4—H4	120.2	C21—C20—C19	117.6 (3)
C3—C4—H4	120.2	C21—C20—N2	116.8 (3)
C4—C5—C6	121.3 (3)	C19—C20—N2	125.5 (3)
C4—C5—H5	119.4	C22—C21—C20	121.9 (3)
C6—C5—H5	119.4	C22—C21—H21	119.1
C7—C6—C5	118.3 (3)	C20—C21—H21	119.1
C7—C6—N1	120.1 (3)	C21—C22—C17	120.8 (3)
C5—C6—N1	121.5 (3)	C21—C22—H22	119.6
C8—C7—C6	121.0 (3)	C17—C22—H22	119.6
C8—C7—H7	119.5	C23—N2—C20	122.5 (3)
C6—C7—H7	119.5	C25—C24—C29	117.9 (3)
C7—C8—C3	119.9 (3)	C25—C24—C23	120.1 (3)
C7—C8—H8	120.0	C29—C24—C23	121.9 (3)
C3—C8—H8	120.0	C24—C25—C26	121.4 (4)
C10—C9—H9A	109.5	C24—C25—H25	119.3
C10—C9—H9B	109.5	C26—C25—H25	119.3
H9A—C9—H9B	109.5	C27—C26—C25	119.5 (4)
C10—C9—H9C	109.5	C27—C26—H26	120.3
H9A—C9—H9C	109.5	C25—C26—H26	120.3
H9B—C9—H9C	109.5	C28—C27—C26	120.5 (4)
O1—C10—C9	107.3 (3)	C28—C27—H27	119.7
O1—C10—H10A	110.3	C26—C27—H27	119.7
C9—C10—H10A	110.3	C27—C28—C29	119.8 (4)
O1—C10—H10B	110.3	C27—C28—H28	120.1
C9—C10—H10B	110.3	C29—C28—H28	120.1
H10A—C10—H10B	108.5	O3—C29—C24	120.8 (3)
C12—C11—C16	119.9 (3)	O3—C29—C28	118.3 (3)
C12—C11—O1	115.1 (3)	C24—C29—C28	120.9 (4)
C16—C11—O1	125.0 (3)	C17—N1—C6	123.0 (3)
C11—C12—C13	120.5 (3)	C17—N1—C14	120.2 (3)
C11—C12—H12	119.7	C6—N1—C14	116.5 (2)
C13—C12—H12	119.7	N2—C23—C24	122.9 (3)
C12—C13—C14	120.2 (3)	N2—C23—H23	118.5
C12—C13—H13	119.9	C24—C23—H23	118.5
C14—C13—H13	119.9	C11—O1—C10	118.3 (3)
C15—C14—C13	119.2 (3)	C3—O2—C2	118.0 (3)
C15—C14—N1	121.0 (3)	C29—O3—H3	109.5
O2—C3—C4—C5	179.0 (3)	C29—C24—C25—C26	−0.3 (8)
C8—C3—C4—C5	−1.2 (5)	C23—C24—C25—C26	−178.7 (5)
C3—C4—C5—C6	0.9 (5)	C24—C25—C26—C27	−0.8 (11)
C4—C5—C6—C7	0.0 (5)	C25—C26—C27—C28	1.1 (11)
C4—C5—C6—N1	−176.9 (3)	C26—C27—C28—C29	−0.3 (9)
C5—C6—C7—C8	−0.5 (5)	C25—C24—C29—O3	−178.7 (4)
N1—C6—C7—C8	176.4 (3)	C23—C24—C29—O3	−0.3 (6)
C6—C7—C8—C3	0.2 (5)	C25—C24—C29—C28	1.1 (7)
O2—C3—C8—C7	−179.6 (3)	C23—C24—C29—C28	179.5 (4)
C4—C3—C8—C7	0.7 (5)	C27—C28—C29—O3	178.9 (5)
C16—C11—C12—C13	−1.1 (5)	C27—C28—C29—C24	−0.8 (7)
O1—C11—C12—C13	178.3 (3)	C22—C17—N1—C6	164.1 (3)
C11—C12—C13—C14	1.0 (5)	C18—C17—N1—C6	−19.1 (5)
C12—C13—C14—C15	−0.2 (5)	C22—C17—N1—C14	−9.9 (5)
C12—C13—C14—N1	178.6 (3)	C18—C17—N1—C14	166.8 (3)
C13—C14—C15—C16	−0.6 (5)	C7—C6—N1—C17	121.5 (3)
N1—C14—C15—C16	−179.4 (3)	C5—C6—N1—C17	−61.7 (4)
C12—C11—C16—C15	0.3 (5)	C7—C6—N1—C14	−64.3 (4)
O1—C11—C16—C15	−179.1 (3)	C5—C6—N1—C14	112.6 (4)
C14—C15—C16—C11	0.6 (5)	C15—C14—N1—C17	−79.1 (4)
N1—C17—C18—C19	−175.8 (3)	C13—C14—N1—C17	102.1 (4)
C22—C17—C18—C19	1.1 (5)	C15—C14—N1—C6	106.4 (4)
C17—C18—C19—C20	0.0 (5)	C13—C14—N1—C6	−72.3 (4)
C18—C19—C20—C21	−0.7 (5)	C20—N2—C23—C24	−177.0 (3)
C18—C19—C20—N2	176.7 (3)	C25—C24—C23—N2	178.0 (4)
C19—C20—C21—C22	0.2 (5)	C29—C24—C23—N2	−0.3 (6)
N2—C20—C21—C22	−177.3 (3)	C12—C11—O1—C10	172.5 (3)
C20—C21—C22—C17	0.9 (6)	C16—C11—O1—C10	−8.2 (5)
N1—C17—C22—C21	175.3 (3)	C9—C10—O1—C11	−176.7 (3)
C18—C17—C22—C21	−1.5 (5)	C4—C3—O2—C2	−10.3 (4)
C21—C20—N2—C23	−170.9 (3)	C8—C3—O2—C2	170.0 (3)
C19—C20—N2—C23	11.7 (5)	C1—C2—O2—C3	−172.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.87	2.605 (4)	148
C1—H1C···Cg2i	0.96	2.84	3.760 (4)	162
C4—H4···Cg3ii	0.93	2.82	3.655 (3)	150
C9—H9C···Cg1iii	0.96	2.94	3.872 (4)	164
C28—H28···Cg1iv	0.93	2.88	3.742 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 Cg2 and Cg3 are the centroids of the C3–C8, C11–C16 and C17–C22 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.87	2.605 (4)	148
C1—H1C⋯Cg2i	0.96	2.84	3.760 (4)	162
C4—H4⋯Cg3ii	0.93	2.82	3.655 (3)	150
C9—H9C⋯Cg1iii	0.96	2.94	3.872 (4)	164
C28—H28⋯Cg1iv	0.93	2.88	3.742 (4)	154

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