(E)-N'-[1-(2-Hy-droxy-phen-yl)ethyl-idene]-2-phen-oxy-acetohydrazide-2,2'-(1,1'-azinodiethyl-idyne)diphenol (2/1).

The formula unit of the title mol-ecular complex, 2C(16)H(16)N(2)O(3)·C(16)H(16)N(2)O(2), consists of two (E)-N'-[1-(2-hy-droxy-phen-yl)ethyl-idene]-2-phen-oxy-acetohydrazide mol-ecules and one mol-ecule of 2,2'-(1,1'-azinodiethyl-idyne)diphenol, with the latter located on a crystallographic inversion center. The acetohydrazide mol-ecules are linked into a supermolecular chain along the c axis by inter-molecular N-H⋯O hydrogen bonds. There are also intra-molecular O-H⋯N hydrogen bonds in both the acetohydrazide and diphenol mol-ecules.

Related literature

For chemically related applications arising from Schiff base compounds, see: Guo et al. (2010 ▶); Yu et al. (2010 ▶). For related structures, see: Lu et al. (1993 ▶); Matoga et al. (2007 ▶); Tai et al. (2008 ▶); Tan (2009 ▶); Wen et al. (2005 ▶).

Experimental

Crystal data

2C16H16N2O3·C16H16N2O2

M = 836.92

Monoclinic,

a = 12.416 (5) Å

b = 19.322 (6) Å

c = 9.225 (4) Å

β = 106.156 (16)°

V = 2125.8 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.18 × 0.15 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.984, T max = 0.988

20592 measured reflections

4828 independent reflections

2586 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.156

S = 1.03

4828 reflections

284 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023956/ld2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023956/ld2015Isup2.hkl

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

C48H48N6O8	F(000) = 884
Mr = 836.92	Dx = 1.308 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20942 reflections
a = 12.416 (5) Å	θ = 3.1–27.5°
b = 19.322 (6) Å	µ = 0.09 mm−1
c = 9.225 (4) Å	T = 293 K
β = 106.156 (16)°	Block, yellow
V = 2125.8 (15) Å3	0.18 × 0.15 × 0.13 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	2586 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→15
Tmin = 0.984, Tmax = 0.988	k = −24→22
20592 measured reflections	l = −11→11

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.318P] where P = (Fo2 + 2Fc2)/3
4828 reflections	(Δ/σ)max < 0.001
284 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

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 > 2sigma(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	0.6516 (2)	0.45868 (12)	0.6050 (3)	0.0530 (6)
C2	0.62855 (18)	0.46636 (10)	0.4481 (3)	0.0436 (5)
C3	0.6718 (2)	0.52452 (12)	0.3947 (3)	0.0559 (6)
H3A	0.6575	0.5308	0.2911	0.067*
C4	0.7351 (2)	0.57283 (12)	0.4910 (3)	0.0676 (8)
H4A	0.7640	0.6109	0.4527	0.081*
C5	0.7553 (2)	0.56461 (13)	0.6431 (3)	0.0714 (8)
H5A	0.7975	0.5975	0.7084	0.086*
C6	0.7140 (2)	0.50842 (13)	0.7003 (3)	0.0702 (8)
H6A	0.7280	0.5036	0.8042	0.084*
C7	0.56243 (18)	0.41504 (11)	0.3420 (2)	0.0434 (5)
C8	0.45215 (18)	0.25229 (11)	0.3911 (3)	0.0435 (5)
C9	0.3965 (2)	0.19347 (11)	0.2898 (3)	0.0528 (6)
H9A	0.3438	0.2122	0.2002	0.063*
H9B	0.4529	0.1676	0.2581	0.063*
C10	0.24130 (19)	0.17197 (11)	0.3878 (2)	0.0452 (6)
C11	0.1875 (2)	0.12496 (13)	0.4551 (3)	0.0589 (7)
H11A	0.2182	0.0812	0.4810	0.071*
C12	0.0881 (2)	0.14261 (17)	0.4840 (3)	0.0728 (8)
H12A	0.0520	0.1108	0.5300	0.087*
C13	0.0425 (2)	0.20653 (18)	0.4457 (4)	0.0790 (9)
H13A	−0.0246	0.2185	0.4656	0.095*
C14	0.0958 (2)	0.25275 (15)	0.3778 (4)	0.0799 (9)
H14A	0.0646	0.2963	0.3512	0.096*
C15	0.1955 (2)	0.23583 (13)	0.3482 (3)	0.0649 (7)
H15A	0.2312	0.2676	0.3016	0.078*
C16	0.5283 (2)	0.42865 (13)	0.1766 (3)	0.0602 (7)
H16A	0.4707	0.3965	0.1273	0.090*
H16B	0.5919	0.4232	0.1378	0.090*
H16C	0.5001	0.4750	0.1580	0.090*
C17	0.8581 (2)	0.08891 (13)	0.6727 (3)	0.0625 (7)
C18	0.86204 (19)	0.11226 (12)	0.8180 (3)	0.0542 (6)
C19	0.8037 (2)	0.17294 (14)	0.8276 (3)	0.0675 (8)
H19A	0.8055	0.1899	0.9226	0.081*
C20	0.7439 (2)	0.20858 (16)	0.7028 (4)	0.0774 (8)
H20A	0.7061	0.2490	0.7133	0.093*
C21	0.7405 (2)	0.18413 (16)	0.5622 (4)	0.0748 (8)
H21A	0.6994	0.2078	0.4770	0.090*
C22	0.7968 (3)	0.12537 (15)	0.5465 (3)	0.0729 (8)
H22A	0.7943	0.1095	0.4505	0.088*
C23	0.9249 (2)	0.07561 (13)	0.9551 (3)	0.0566 (7)
C24	0.9348 (3)	0.10499 (16)	1.1066 (3)	0.0816 (9)
H24A	1.0123	0.1058	1.1639	0.122*
H24B	0.8931	0.0769	1.1578	0.122*
H24C	0.9055	0.1513	1.0963	0.122*
N1	0.53908 (15)	0.35937 (9)	0.4040 (2)	0.0459 (5)
N2	0.47974 (15)	0.30681 (9)	0.3170 (2)	0.0471 (5)
H2A	0.4611	0.3086	0.2200	0.057*
N3	0.97077 (17)	0.01712 (11)	0.9343 (2)	0.0608 (6)
O1	0.61634 (17)	0.40377 (9)	0.67081 (19)	0.0729 (6)
H01A	0.5821	0.3756	0.5844	0.107 (11)*
O2	0.47137 (14)	0.25029 (7)	0.52807 (18)	0.0522 (4)
O3	0.33937 (14)	0.14856 (7)	0.36327 (18)	0.0517 (4)
O4	0.91241 (19)	0.03129 (10)	0.6491 (2)	0.0892 (7)
H04A	0.9261	0.0087	0.7578	0.175 (18)*

	U11	U22	U33	U12	U13	U23
C1	0.0671 (16)	0.0455 (13)	0.0432 (15)	0.0023 (12)	0.0097 (12)	−0.0008 (11)
C2	0.0467 (13)	0.0408 (12)	0.0417 (14)	0.0041 (10)	0.0097 (11)	0.0026 (10)
C3	0.0655 (16)	0.0484 (14)	0.0511 (16)	0.0014 (13)	0.0115 (13)	0.0074 (12)
C4	0.0721 (18)	0.0443 (14)	0.077 (2)	−0.0063 (13)	0.0051 (15)	0.0030 (14)
C5	0.082 (2)	0.0483 (15)	0.067 (2)	−0.0021 (14)	−0.0082 (16)	−0.0069 (13)
C6	0.095 (2)	0.0567 (16)	0.0462 (17)	−0.0006 (15)	−0.0006 (15)	−0.0079 (12)
C7	0.0485 (13)	0.0463 (12)	0.0365 (13)	0.0032 (11)	0.0135 (10)	0.0031 (10)
C8	0.0501 (13)	0.0475 (13)	0.0368 (14)	−0.0013 (11)	0.0184 (11)	−0.0025 (10)
C9	0.0664 (15)	0.0532 (14)	0.0450 (15)	−0.0109 (12)	0.0257 (12)	−0.0062 (11)
C10	0.0502 (14)	0.0469 (13)	0.0371 (13)	−0.0058 (11)	0.0099 (11)	−0.0008 (10)
C11	0.0601 (16)	0.0634 (15)	0.0513 (16)	−0.0061 (13)	0.0122 (13)	0.0148 (12)
C12	0.0552 (17)	0.103 (2)	0.061 (2)	−0.0151 (17)	0.0167 (14)	0.0130 (16)
C13	0.0546 (17)	0.102 (2)	0.081 (2)	0.0014 (18)	0.0205 (16)	−0.0114 (19)
C14	0.0607 (18)	0.0661 (18)	0.111 (3)	0.0056 (15)	0.0202 (18)	−0.0032 (17)
C15	0.0617 (17)	0.0495 (15)	0.085 (2)	−0.0031 (13)	0.0225 (15)	0.0097 (13)
C16	0.0799 (18)	0.0588 (15)	0.0392 (15)	−0.0051 (14)	0.0122 (13)	0.0047 (11)
C17	0.0699 (17)	0.0546 (15)	0.0647 (19)	−0.0133 (14)	0.0217 (15)	−0.0017 (14)
C18	0.0477 (14)	0.0530 (14)	0.0611 (18)	−0.0111 (12)	0.0138 (12)	−0.0037 (12)
C19	0.0584 (17)	0.0710 (17)	0.070 (2)	0.0003 (14)	0.0131 (15)	−0.0035 (15)
C20	0.0686 (19)	0.0786 (19)	0.083 (2)	0.0091 (16)	0.0178 (17)	0.0099 (18)
C21	0.0653 (18)	0.081 (2)	0.074 (2)	−0.0061 (16)	0.0125 (16)	0.0181 (17)
C22	0.082 (2)	0.0755 (19)	0.060 (2)	−0.0186 (17)	0.0184 (16)	0.0027 (15)
C23	0.0489 (14)	0.0579 (15)	0.0606 (18)	−0.0113 (12)	0.0111 (13)	−0.0047 (13)
C24	0.092 (2)	0.085 (2)	0.060 (2)	0.0082 (17)	0.0077 (16)	−0.0106 (16)
N1	0.0550 (12)	0.0468 (11)	0.0351 (11)	−0.0057 (9)	0.0112 (9)	−0.0037 (9)
N2	0.0601 (12)	0.0511 (11)	0.0301 (11)	−0.0107 (10)	0.0125 (9)	−0.0029 (8)
N3	0.0591 (13)	0.0617 (14)	0.0585 (15)	−0.0062 (11)	0.0112 (11)	0.0014 (10)
O1	0.1084 (15)	0.0686 (11)	0.0381 (11)	−0.0196 (11)	0.0143 (10)	0.0011 (9)
O2	0.0677 (11)	0.0575 (10)	0.0346 (10)	−0.0049 (8)	0.0193 (8)	−0.0016 (7)
O3	0.0626 (10)	0.0432 (8)	0.0565 (11)	−0.0034 (8)	0.0284 (9)	0.0022 (7)
O4	0.1350 (19)	0.0682 (12)	0.0699 (15)	0.0083 (13)	0.0374 (13)	−0.0032 (11)

C1—O1	1.354 (3)	C14—C15	1.379 (4)
C1—C6	1.385 (3)	C14—H14A	0.9300
C1—C2	1.404 (3)	C15—H15A	0.9300
C2—C3	1.393 (3)	C16—H16A	0.9600
C2—C7	1.472 (3)	C16—H16B	0.9600
C3—C4	1.375 (3)	C16—H16C	0.9600
C3—H3A	0.9300	C17—O4	1.351 (3)
C4—C5	1.364 (4)	C17—C22	1.391 (4)
C4—H4A	0.9300	C17—C18	1.402 (4)
C5—C6	1.368 (4)	C18—C19	1.394 (3)
C5—H5A	0.9300	C18—C23	1.471 (3)
C6—H6A	0.9300	C19—C20	1.370 (4)
C7—N1	1.289 (3)	C19—H19A	0.9300
C7—C16	1.489 (3)	C20—C21	1.369 (4)
C8—O2	1.219 (3)	C20—H20A	0.9300
C8—N2	1.351 (3)	C21—C22	1.362 (4)
C8—C9	1.511 (3)	C21—H21A	0.9300
C9—O3	1.408 (3)	C22—H22A	0.9300
C9—H9A	0.9700	C23—N3	1.303 (3)
C9—H9B	0.9700	C23—C24	1.481 (4)
C10—C15	1.365 (3)	C24—H24A	0.9600
C10—C11	1.373 (3)	C24—H24B	0.9600
C10—O3	1.376 (3)	C24—H24C	0.9600
C11—C12	1.376 (4)	N1—N2	1.375 (2)
C11—H11A	0.9300	N2—H2A	0.8600
C12—C13	1.364 (4)	N3—N3i	1.394 (4)
C12—H12A	0.9300	O1—H01A	0.9610
C13—C14	1.364 (4)	O4—H04A	1.0635
C13—H13A	0.9300
O1—C1—C6	117.0 (2)	C10—C15—C14	119.4 (3)
O1—C1—C2	123.1 (2)	C10—C15—H15A	120.3
C6—C1—C2	119.9 (2)	C14—C15—H15A	120.3
C3—C2—C1	117.5 (2)	C7—C16—H16A	109.5
C3—C2—C7	120.4 (2)	C7—C16—H16B	109.5
C1—C2—C7	122.0 (2)	H16A—C16—H16B	109.5
C4—C3—C2	121.8 (2)	C7—C16—H16C	109.5
C4—C3—H3A	119.1	H16A—C16—H16C	109.5
C2—C3—H3A	119.1	H16B—C16—H16C	109.5
C5—C4—C3	119.6 (3)	O4—C17—C22	117.6 (3)
C5—C4—H4A	120.2	O4—C17—C18	122.2 (3)
C3—C4—H4A	120.2	C22—C17—C18	120.2 (3)
C4—C5—C6	120.5 (2)	C19—C18—C17	116.8 (2)
C4—C5—H5A	119.7	C19—C18—C23	120.7 (2)
C6—C5—H5A	119.7	C17—C18—C23	122.5 (2)
C5—C6—C1	120.7 (3)	C20—C19—C18	122.6 (3)
C5—C6—H6A	119.7	C20—C19—H19A	118.7
C1—C6—H6A	119.7	C18—C19—H19A	118.7
N1—C7—C2	114.8 (2)	C21—C20—C19	119.3 (3)
N1—C7—C16	124.6 (2)	C21—C20—H20A	120.3
C2—C7—C16	120.62 (19)	C19—C20—H20A	120.3
O2—C8—N2	123.0 (2)	C22—C21—C20	120.5 (3)
O2—C8—C9	122.8 (2)	C22—C21—H21A	119.8
N2—C8—C9	114.2 (2)	C20—C21—H21A	119.8
O3—C9—C8	111.74 (19)	C21—C22—C17	120.7 (3)
O3—C9—H9A	109.3	C21—C22—H22A	119.7
C8—C9—H9A	109.3	C17—C22—H22A	119.7
O3—C9—H9B	109.3	N3—C23—C18	116.1 (2)
C8—C9—H9B	109.3	N3—C23—C24	123.1 (2)
H9A—C9—H9B	107.9	C18—C23—C24	120.8 (2)
C15—C10—C11	120.0 (2)	C23—C24—H24A	109.5
C15—C10—O3	125.1 (2)	C23—C24—H24B	109.5
C11—C10—O3	114.9 (2)	H24A—C24—H24B	109.5
C10—C11—C12	119.9 (2)	C23—C24—H24C	109.5
C10—C11—H11A	120.0	H24A—C24—H24C	109.5
C12—C11—H11A	120.0	H24B—C24—H24C	109.5
C13—C12—C11	120.3 (3)	C7—N1—N2	120.49 (19)
C13—C12—H12A	119.9	C8—N2—N1	116.77 (19)
C11—C12—H12A	119.9	C8—N2—H2A	121.6
C14—C13—C12	119.5 (3)	N1—N2—H2A	121.6
C14—C13—H13A	120.3	C23—N3—N3i	115.2 (3)
C12—C13—H13A	120.3	C1—O1—H01A	101.2
C13—C14—C15	120.9 (3)	C10—O3—C9	117.65 (17)
C13—C14—H14A	119.6	C17—O4—H04A	98.1
C15—C14—H14A	119.6
O1—C1—C2—C3	−178.5 (2)	O4—C17—C18—C19	179.1 (2)
C6—C1—C2—C3	0.8 (3)	C22—C17—C18—C19	−0.8 (4)
O1—C1—C2—C7	0.8 (4)	O4—C17—C18—C23	−0.4 (4)
C6—C1—C2—C7	−179.9 (2)	C22—C17—C18—C23	179.7 (2)
C1—C2—C3—C4	0.2 (4)	C17—C18—C19—C20	0.6 (4)
C7—C2—C3—C4	−179.1 (2)	C23—C18—C19—C20	−179.8 (2)
C2—C3—C4—C5	−0.9 (4)	C18—C19—C20—C21	0.1 (4)
C3—C4—C5—C6	0.6 (4)	C19—C20—C21—C22	−0.7 (4)
C4—C5—C6—C1	0.4 (4)	C20—C21—C22—C17	0.5 (4)
O1—C1—C6—C5	178.3 (3)	O4—C17—C22—C21	−179.7 (3)
C2—C1—C6—C5	−1.1 (4)	C18—C17—C22—C21	0.3 (4)
C3—C2—C7—N1	171.5 (2)	C19—C18—C23—N3	175.8 (2)
C1—C2—C7—N1	−7.7 (3)	C17—C18—C23—N3	−4.7 (3)
C3—C2—C7—C16	−7.9 (3)	C19—C18—C23—C24	−4.6 (4)
C1—C2—C7—C16	172.8 (2)	C17—C18—C23—C24	174.9 (2)
O2—C8—C9—O3	18.8 (3)	C2—C7—N1—N2	−178.66 (18)
N2—C8—C9—O3	−161.82 (19)	C16—C7—N1—N2	0.7 (3)
C15—C10—C11—C12	−0.8 (4)	O2—C8—N2—N1	4.7 (3)
O3—C10—C11—C12	−179.5 (2)	C9—C8—N2—N1	−174.67 (19)
C10—C11—C12—C13	0.3 (4)	C7—N1—N2—C8	−175.6 (2)
C11—C12—C13—C14	0.2 (5)	C18—C23—N3—N3i	−179.5 (2)
C12—C13—C14—C15	−0.3 (5)	C24—C23—N3—N3i	0.9 (4)
C11—C10—C15—C14	0.7 (4)	C15—C10—O3—C9	−0.9 (3)
O3—C10—C15—C14	179.3 (2)	C11—C10—O3—C9	177.8 (2)
C13—C14—C15—C10	−0.2 (5)	C8—C9—O3—C10	72.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ii	0.86	2.14	2.860 (3)	141
O1—H01A···N1	0.96	1.63	2.530 (3)	154
O4—H04A···N3	1.06	1.58	2.542 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.14	2.860 (3)	141
O1—H01A⋯N1	0.96	1.63	2.530 (3)	154
O4—H04A⋯N3	1.06	1.58	2.542 (3)	148

Symmetry code: (i) .