(E)-N′-[1-(2-Hy­droxy­phen­yl)ethyl­idene]-2-phen­oxy­acetohydrazide–2,2′-(1,1′-azinodiethyl­idyne)diphenol (2/1)

Tang, Y.-R.

doi:10.1107/S1600536811023956

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1819

doi:10.1107/S1600536811023956

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(E)-N′-[1-(2-Hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide–2,2′-(1,1′-azinodiethylidyne)diphenol (2/1)

Yan-Ru Tang ^a ^*

^aDepartment of Chemistry, Changchun Normal University, Changchun 130032, People's Republic of China
^*Correspondence e-mail: yrtang62@gmail.com

(Received 2 June 2011; accepted 19 June 2011; online 25 June 2011)

The formula unit of the title molecular complex, 2C₁₆H₁₆N₂O₃·C₁₆H₁₆N₂O₂, consists of two (E)-N′-[1-(2-hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide molecules and one molecule of 2,2′-(1,1′-azinodiethylidyne)diphenol, with the latter located on a crystallographic inversion center. The acetohydrazide molecules are linked into a supermolecular chain along the c axis by intermolecular N—H⋯O hydrogen bonds. There are also intramolecular O—H⋯N hydrogen bonds in both the acetohydrazide and diphenol molecules.

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_r = 836.92
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.156
S = 1.03
4828 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811023956/ld2015sup1.cif

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

checkCIF report

Comment top

Among the richness of coordination chemistry, acylhydrazone ligands (Yu et al., 2010) have attracted an intense interest due to their potential for magnetochemistry (Guo et al., 2010). Recently, a large number of acylhydrazone derivatives have been prepared (Matoga et al., 2007; Tan, 2009). As a contribution to this field, the isolation and the structure of the title 2/1 co-crystal are presented here .

The molecular structure of 2C₁₆H₁₆N₂O₃.C₁₆H₁₆N₂O₂, together with the atom-numbering scheme, is illustrated in Fig.1. Selected bond lengths and angles are given in Table 1. The asymmetric unit of the title co-crystal comprises two (E)-N'-(1-(2-hydroxyphenyl)ethylidene)-2-phenoxyacetohydrazide (A) molecules and a molecule of 2,2'-(1,1'-Azinodiethylidyne)diphenol (B), with no proton transfer. The 2,2'-(1,1'-Azinodiethylidyne)diphenol molecule (B) has been reported previously (Tai et al., 2008). The N3—N3A (1.394 (4) Å) distance is similar to the corresponding distances observed for other compounds (Lu et al., 1993). In the molecule A, the N1—N2(hydrazine) bond distance of 1.375 (2) Å is shorter than the corresponding N—N value of 1.382 (2) Å in a related compound (Wen et al., 2005). The dihedral angle between both aromatic rings for molecule A is 85.76 (2)°, and the molecules A are linked into supermolecule chain along the c axis by intermolecular N2—H2A···O2I hydrogen bonds [symmetry code: (I) x, 1/2 - y, -1/2 + z] (Fig. 2). In addition, there are intramolecular O1—H01A···N1 and O4—H04A···N3 hydrogen bonds in molecules A and B respectively. Stacking interactions between A and B are within van der Waals contacts (Fig.3).

Related literature top

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 top

A solution of 2,2'-(1,1'-azinodiethylidyne)diphenol (0.2 mmol) in 10 ml of EtOH was added to a solution of (E)-N'-(1-(2-hydroxyphenyl)ethylidene) -2-phenoxyacetohydrazide (0.2 mmol) in 10 ml of the same solvent, upon which the solution was refluxed for 1 h. Then the yellow solution was obtained after filtering. Two week later, yellow crystals of the title compound were isolated from the solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title organic compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. One-dimensional chain structure of molecules A. Hydrogen bonds are shown as green dashed lines [symmetry code: (I) x, 1/2 - y, -1/2 + z].
	Fig. 3. Packing diagram of molecules A (blue bonds) and B (orange bands).

(E)-N'-[1-(2-Hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide– 2,2'-(1,1'-azinodiethylidyne)diphenol (2/1) top

Crystal data top

C₄₈H₄₈N₆O₈	F(000) = 884
M_r = 836.92	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0615P)² + 0.318P] where P = (F_o² + 2F_c²)/3
4828 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₄₈H₄₈N₆O₈	V = 2125.8 (15) Å³
M_r = 836.92	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.416 (5) Å	µ = 0.09 mm⁻¹
b = 19.322 (6) Å	T = 293 K
c = 9.225 (4) Å	0.18 × 0.15 × 0.13 mm
β = 106.156 (16)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4828 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2586 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.988	R_int = 0.072
20592 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
4828 reflections	Δρ_min = −0.19 e Å⁻³
284 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄₈H₄₈N₆O₈
M_r	836.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.416 (5), 19.322 (6), 9.225 (4)
β (°)	106.156 (16)
V (Å³)	2125.8 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.15 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.984, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	20592, 4828, 2586
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.156, 1.03
No. of reflections	4828
No. of parameters	284
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2.

Acknowledgements

The author thanks Changchun Normal University for financial support.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Guo, Y.-N., Xu, G.-F., Gamez, P., Zhao, L., Lin, S.-Y., Deng, R., Tang, J.-K. & Zhang, H.-J. (2010). J. Am. Chem. Soc. 132, 8538–8539. Web of Science CSD CrossRef CAS PubMed Google Scholar
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Volume 67| Part 7| July 2011| Page o1819

doi:10.1107/S1600536811023956

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-[1-(2-Hy­dr­oxy­phen­yl)ethyl­­idene]-2-phen­­oxy­acetohydrazide–2,2′-(1,1′-azinodi­ethyl­­idyne)diphenol (2/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-[1-(2-Hydroxyphenyl)ethylidene]-2-phenoxyacetohydrazide–2,2′-(1,1′-azinodiethylidyne)diphenol (2/1)