2,2′-Dihydroxy-3,3′-[(1E,1′E)-hydrazine-1,2-diylidenedimethylidyne]dibenzoic acid N,N-dimethylformamide disolvate

Zhang, S.-S.; Cheng, G.-J.-S.; Lei, Y.; Li, Y.-B.

doi:10.1107/S1600536808043134

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Pages o194-o195

doi:10.1107/S1600536808043134

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2,2′-Dihydroxy-3,3′-[(1E,1′E)-hydrazine-1,2-diylidenedimethylidyne]dibenzoic acid N,N-dimethylformamide disolvate

Sheng-Sen Zhang,^a Geng-Jin-Sheng Cheng,^a ^* Yu Lei ^a and Yin-Bao Li ^a

^aCollege of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000, People's Republic of China
^*Correspondence e-mail: chengyong2008@gmail.com

(Received 7 December 2008; accepted 18 December 2008; online 24 December 2008)

The title compound, C₁₆H₁₂N₂O₆·2C₃H₇NO, lies across a crystallographic inversion centre which is situated at the midpoint of the central N—N bond. The substitution at the C=N bond adopts a trans configuration and it is essentially coplanar with the benzene ring [N—C—C—C torsion angles = −173.9 (4) and 6.4 (6)°]. All torsion angles involving non-H atoms are close to 180°. Intramolecular O—H⋯O and weak C—H⋯O hydrogen bonds form S(6) and S(5) ring motifs, respectively, while intermolecular O—H⋯O and weak C—H⋯O hydrogen bonds connect the Schiff base molecule to solvent dimethylformamide molecules.

Related literature

For information on Schiff base ligands, their complexes and their applications, see, for example: Pal et al. (2005 ); Hou et al. (2001 ); Ren et al. (2002 ). For bond-length data, see: Allen et al. (1987 ). For the structures and properties of related azine organic and metallorganic compounds, see, for example: Dreuw et al. (2005 ); Chattopadhyay et al. (2008 ); Cucos et al. (2006 ); Fu (2007 ); Mijanuddina et al. (2004 ); Sreerama et al. (2007 ); Butcher et al. (2007 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₆·2C₃H₇NO
M_r = 474.47
Monoclinic, P 2₁ /c
a = 5.9136 (12) Å
b = 10.837 (2) Å
c = 18.991 (4) Å
β = 98.96 (3)°
V = 1202.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.36 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.965, T_max = 0.984
7616 measured reflections
1978 independent reflections
679 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.149
S = 1.01
1978 reflections
159 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Selected torsion angles (°)

C7—C1—C2—C3	179.5 (4)
C3—C4—C5—C8	179.5 (4)
C4—C5—C6—O3	−179.5 (4)
C8—C5—C6—C1	−180.0 (4)
C7—C1—C6—C5	−179.2 (4)
C6—C1—C7—O2	174.1 (4)
N1ⁱ—N1—C8—C5	−179.4 (4)
C6—C5—C8—N1	−173.9 (4)
C11—N2—C9—O4	178.3 (5)
Symmetry code: (i) -x+2, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱⁱ	0.93	2.59	3.261 (6)	130
C2—H2A⋯O2	0.93	2.43	2.742 (6)	99
O3—H3⋯O1	0.82	1.85	2.568 (4)	146
O2—H2⋯O4ⁱⁱⁱ	0.82	1.76	2.557 (4)	162
Symmetry codes: (ii) x+1, y, z; (iii) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043134/lh2745sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043134/lh2745Isup2.hkl

checkCIF report

Comment top

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry. Schiff bases have been used widely as ligands in the formation of transition metal complexes. There has been growing interest in Schiff base ligands, mainly because of their wide application in the field of biochemistry, synthesis, and catalysis (Pal et al., 2005; Hou et al., 2001; Ren et al., 2002).

Herein, we report the synthesis and crystal structure of the Schiff-base compound, (I). The molecule lies across a crystallographic inversion centre which is situated at the midpoint of the N—N (1.393 (6) Å) bond. The molecular structure of (I) is shown in Fig.1. All bond lengths are within in normal ranges (Allen et al., 1987). The N1—C8 [1.281 (5) Å] and N1—N1ⁱ [1.393 (6) Å] (symmetry code: (i) -x+2, -y+2, -z+1) distances indicate these correspond to double and single bonds, respectively. The torsion angles indicate that the molecule is essentially planar with the C=N bond adjacent to the benzene rings adopting a trans configuration with resect to its substitution. Intramolecular O—H···O and C—H···O hydrogen bonds form S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995). The Schiff-base molecule and solvent DMF molecules are connected by intermolecular hydrogen bonds (Fig.1 and Table. 2). Some crystal structures which are closely related to the title compound have already been studied (Chattopadhyay et al.,2008; Cucos et al., 2006; Fu, 2007; Mijanuddina et al., 2004; Dreuw et al., 2005; Sreerama et al., 2007).

Related literature top

For information on Schiff base ligands, their complexes and their applications, see, for example: Pal et al. (2005); Hou et al. (2001); Ren et al. (2002). For bond-length data, see: Allen et al. (1987). For related azine organic, metallorganic compound structures and properities, see, for example: Dreuw et al. (2005); Chattopadhyay et al. (2008); Cucos et al. (2006); Fu et al. (2007); Mijanuddina et al. (2004); Sreerama et al. (2007). For related literature, see: Bernstein et al. (1995); Butcher et al. (2007).

Experimental top

Reagents and solvents used were of commercially available quality. To a stirred solution of 3-formylsalicylic acid (0.332 g, 2 mmol) in absolute methanol (10 ml) was added dropwise hydrazine hydrate (0.050 g, 1 mmol). After a few minutes, an orange precipitate appeared, which was isolated by filtration, washed with methanol, and dried in air. Crystals of (I) suitable for X-ray diffraction were obtained by recrystallized the crude product from DMF solution.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure with displacement ellipsoids at the 30% probability level. Hydrogen bonds show as dashed lines.

2,2'-Dihydroxy-3,3'-[(1E,1'E)-hydrazine-1,2- diylidenedimethylidyne]dibenzoic acid N,N-dimethylformamide disolvate top

Crystal data top

C₁₆H₁₂N₂O₆·2C₃H₇NO	F(000) = 500
M_r = 474.47	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.9136 (12) Å	Cell parameters from 812 reflections
b = 10.837 (2) Å	θ = 2.1–15.4°
c = 18.991 (4) Å	µ = 0.10 mm⁻¹
β = 98.96 (3)°	T = 295 K
V = 1202.2 (4) Å³	Needle, red
Z = 2	0.36 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1978 independent reflections
Radiation source: fine-focus sealed tube	679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.965, T_max = 0.984	k = −12→12
7616 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.036P)² + 0.022P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1978 reflections	Δρ_max = 0.14 e Å⁻³
159 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (4)

Crystal data top

C₁₆H₁₂N₂O₆·2C₃H₇NO	V = 1202.2 (4) Å³
M_r = 474.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.9136 (12) Å	µ = 0.10 mm⁻¹
b = 10.837 (2) Å	T = 295 K
c = 18.991 (4) Å	0.36 × 0.20 × 0.16 mm
β = 98.96 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1978 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	679 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.984	R_int = 0.082
7616 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
1978 reflections	Δρ_min = −0.14 e Å⁻³
159 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.9469 (6)	0.9471 (3)	0.51035 (19)	0.0850 (12)
N2	0.2954 (7)	0.6509 (3)	0.23059 (19)	0.0830 (11)
O1	−0.0194 (5)	0.7647 (3)	0.34383 (15)	0.0925 (10)
O2	−0.0718 (5)	0.5919 (3)	0.40230 (16)	0.0978 (10)
H2	−0.1983	0.5948	0.3775	0.147*
O3	0.3501 (5)	0.8896 (3)	0.37878 (14)	0.0913 (10)
H3	0.2293	0.8697	0.3541	0.137*
O4	0.5660 (5)	0.5621 (3)	0.31107 (17)	0.1024 (11)
C1	0.2520 (8)	0.7119 (4)	0.4437 (2)	0.0735 (12)
C2	0.3105 (8)	0.6335 (4)	0.5012 (2)	0.0901 (14)
H2A	0.2151	0.5678	0.5079	0.108*
C3	0.5105 (10)	0.6525 (5)	0.5488 (2)	0.1046 (16)
H3A	0.5491	0.6001	0.5877	0.126*
C4	0.6512 (8)	0.7496 (5)	0.5380 (2)	0.0977 (16)
H4	0.7858	0.7614	0.5698	0.117*
C5	0.5984 (8)	0.8308 (4)	0.4808 (2)	0.0753 (13)
C6	0.3970 (8)	0.8102 (4)	0.4342 (2)	0.0717 (12)
C7	0.0427 (8)	0.6924 (5)	0.3928 (3)	0.0782 (13)
C8	0.7514 (9)	0.9333 (4)	0.4714 (2)	0.0829 (13)
H8	0.7050	0.9909	0.4357	0.099*
C9	0.4849 (9)	0.6507 (5)	0.2750 (3)	0.0863 (14)
H9	0.5674	0.7240	0.2801	0.104*
C10	0.1512 (9)	0.5403 (4)	0.2220 (2)	0.1212 (18)
H10A	0.2158	0.4811	0.1933	0.182*
H10B	0.0001	0.5622	0.1993	0.182*
H10C	0.1433	0.5052	0.2680	0.182*
C11	0.2066 (9)	0.7591 (5)	0.1912 (3)	0.1217 (18)
H11A	0.3080	0.8274	0.2039	0.183*
H11B	0.0579	0.7784	0.2024	0.183*
H11C	0.1949	0.7432	0.1410	0.183*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.066 (3)	0.093 (3)	0.091 (3)	0.006 (2)	0.000 (2)	−0.007 (2)
N2	0.079 (3)	0.082 (3)	0.085 (3)	−0.017 (2)	0.005 (2)	−0.005 (2)
O1	0.093 (2)	0.093 (2)	0.084 (2)	0.0066 (18)	−0.0070 (18)	0.0125 (17)
O2	0.089 (2)	0.093 (2)	0.107 (3)	−0.003 (2)	0.0012 (19)	0.0162 (19)
O3	0.096 (2)	0.094 (2)	0.079 (2)	−0.0056 (18)	−0.0022 (17)	0.0103 (17)
O4	0.098 (3)	0.085 (2)	0.116 (3)	−0.001 (2)	−0.010 (2)	0.0036 (19)
C1	0.071 (3)	0.078 (3)	0.072 (3)	0.009 (3)	0.014 (3)	0.000 (3)
C2	0.092 (4)	0.098 (3)	0.080 (3)	0.001 (3)	0.015 (3)	0.008 (3)
C3	0.104 (4)	0.124 (4)	0.080 (3)	0.018 (4)	−0.003 (3)	0.022 (3)
C4	0.085 (4)	0.119 (4)	0.082 (4)	0.009 (3)	−0.009 (3)	0.005 (3)
C5	0.083 (3)	0.077 (3)	0.063 (3)	0.021 (3)	0.002 (3)	−0.008 (3)
C6	0.078 (3)	0.075 (3)	0.062 (3)	0.021 (3)	0.011 (3)	0.001 (2)
C7	0.075 (3)	0.069 (3)	0.090 (4)	0.013 (3)	0.012 (3)	−0.006 (3)
C8	0.089 (4)	0.079 (3)	0.082 (3)	0.020 (3)	0.018 (3)	−0.009 (2)
C9	0.076 (4)	0.090 (4)	0.094 (4)	−0.012 (3)	0.014 (3)	−0.007 (3)
C10	0.126 (5)	0.116 (4)	0.123 (4)	−0.042 (4)	0.023 (4)	−0.037 (3)
C11	0.118 (4)	0.118 (4)	0.120 (4)	−0.009 (3)	−0.008 (3)	0.023 (3)

Geometric parameters (Å, º) top

N1—C8	1.281 (5)	C2—H2A	0.9300
N1—N1ⁱ	1.393 (6)	C3—C4	1.377 (6)
N2—C9	1.293 (5)	C3—H3A	0.9300
N2—C11	1.445 (5)	C4—C5	1.395 (5)
N2—C10	1.465 (5)	C4—H4	0.9300
O1—C7	1.228 (5)	C5—C6	1.387 (5)
O2—C7	1.310 (5)	C5—C8	1.462 (6)
O2—H2	0.8200	C8—H8	0.9300
O3—C6	1.354 (4)	C9—H9	0.9300
O3—H3	0.8200	C10—H10A	0.9600
O4—C9	1.232 (5)	C10—H10B	0.9600
C1—C2	1.384 (5)	C10—H10C	0.9600
C1—C6	1.397 (5)	C11—H11A	0.9600
C1—C7	1.462 (5)	C11—H11B	0.9600
C2—C3	1.388 (6)	C11—H11C	0.9600

C8—N1—N1ⁱ	109.8 (5)	C5—C6—C1	121.6 (4)
C9—N2—C11	123.2 (4)	O1—C7—O2	122.3 (4)
C9—N2—C10	120.1 (4)	O1—C7—C1	122.1 (5)
C11—N2—C10	116.6 (4)	O2—C7—C1	115.6 (4)
C7—O2—H2	109.5	N1—C8—C5	122.5 (4)
C6—O3—H3	109.5	N1—C8—H8	118.7
C2—C1—C6	119.1 (4)	C5—C8—H8	118.7
C2—C1—C7	121.0 (5)	O4—C9—N2	125.9 (5)
C6—C1—C7	119.9 (4)	O4—C9—H9	117.0
C1—C2—C3	120.4 (5)	N2—C9—H9	117.0
C1—C2—H2A	119.8	N2—C10—H10A	109.5
C3—C2—H2A	119.8	N2—C10—H10B	109.5
C4—C3—C2	119.3 (4)	H10A—C10—H10B	109.5
C4—C3—H3A	120.4	N2—C10—H10C	109.5
C2—C3—H3A	120.4	H10A—C10—H10C	109.5
C3—C4—C5	122.1 (5)	H10B—C10—H10C	109.5
C3—C4—H4	118.9	N2—C11—H11A	109.5
C5—C4—H4	118.9	N2—C11—H11B	109.5
C6—C5—C4	117.5 (5)	H11A—C11—H11B	109.5
C6—C5—C8	122.0 (4)	N2—C11—H11C	109.5
C4—C5—C8	120.5 (4)	H11A—C11—H11C	109.5
O3—C6—C5	116.5 (5)	H11B—C11—H11C	109.5
O3—C6—C1	121.9 (4)

C6—C1—C2—C3	0.1 (6)	C2—C1—C6—C5	0.3 (6)
C7—C1—C2—C3	179.5 (4)	C7—C1—C6—C5	−179.2 (4)
C1—C2—C3—C4	−0.5 (7)	C2—C1—C7—O1	175.7 (4)
C2—C3—C4—C5	0.6 (8)	C6—C1—C7—O1	−4.9 (6)
C3—C4—C5—C6	−0.3 (7)	C2—C1—C7—O2	−5.4 (6)
C3—C4—C5—C8	179.5 (4)	C6—C1—C7—O2	174.1 (4)
C4—C5—C6—O3	−179.5 (4)	N1ⁱ—N1—C8—C5	−179.4 (4)
C8—C5—C6—O3	0.7 (6)	C6—C5—C8—N1	−173.9 (4)
C4—C5—C6—C1	−0.2 (6)	C4—C5—C8—N1	6.4 (6)
C8—C5—C6—C1	−180.0 (4)	C11—N2—C9—O4	178.3 (5)
C2—C1—C6—O3	179.5 (4)	C10—N2—C9—O4	2.7 (7)
C7—C1—C6—O3	0.1 (6)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱⁱ	0.93	2.59	3.261 (6)	130
C2—H2A···O2	0.93	2.43	2.742 (6)	99
O3—H3···O1	0.82	1.85	2.568 (4)	146
O2—H2···O4ⁱⁱⁱ	0.82	1.76	2.557 (4)	162

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₆·2C₃H₇NO
M_r	474.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	5.9136 (12), 10.837 (2), 18.991 (4)
β (°)	98.96 (3)
V (Å³)	1202.2 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.965, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7616, 1978, 679
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.149, 1.01
No. of reflections	1978
No. of parameters	159
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected torsion angles (º) top

C7—C1—C2—C3	179.5 (4)	C6—C1—C7—O2	174.1 (4)
C3—C4—C5—C8	179.5 (4)	N1ⁱ—N1—C8—C5	−179.4 (4)
C4—C5—C6—O3	−179.5 (4)	C6—C5—C8—N1	−173.9 (4)
C8—C5—C6—C1	−180.0 (4)	C11—N2—C9—O4	178.3 (5)
C7—C1—C6—C5	−179.2 (4)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱⁱ	0.93	2.59	3.261 (6)	129.5
C2—H2A···O2	0.93	2.43	2.742 (6)	99.4
O3—H3···O1	0.82	1.85	2.568 (4)	146.2
O2—H2···O4ⁱⁱⁱ	0.82	1.76	2.557 (4)	161.9

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z.

Acknowledgements

This work was supported by the Key Laboratory for Research and Development of Natural Drugs of Jiangxi Province. The data were collected and the structure solved and refined at the Department of Chemistry and Biology, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China.

References

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Volume 65| Part 1| January 2009| Pages o194-o195

doi:10.1107/S1600536808043134

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

2,2′-Di­hydroxy-3,3′-[(1E,1′E)-hydrazine-1,2-diylidenedi­methyl­idyne]di­benzoic acid N,N-di­methylformamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-Dihydroxy-3,3′-[(1E,1′E)-hydrazine-1,2-diylidenedimethylidyne]dibenzoic acid N,N-dimethylformamide disolvate