N′-(3,4-Dimeth­oxy­benzyl­idene)-3,5-dihy­droxy­benzohydrazide methanol monosolvate

Zhang, Q.-H.; Zhou, L.-D.; Li, C.-X.; Huang, S.-S.; Zhang, B.-J.

doi:10.1107/S1600536811029850

organic compounds

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Volume 67| Part 8| August 2011| Page o2189

doi:10.1107/S1600536811029850

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N′-(3,4-Dimethoxybenzylidene)-3,5-dihydroxybenzohydrazide methanol monosolvate

Qi-Hui Zhang,^a ^* Lian-Di Zhou,^b Chuan-Xun Li,^c Shan-Shan Huang ^c and Bao-Jing Zhang ^c

^aCollege of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030, People's Republic of China, ^bDepartment of Immunology, Basic Medical College, Chongqing Medical University, Chongqing 400016, People's Republic of China, and ^cSchool of Pharmacy, Dalian Medical University, Dalian 116044, People's Republic of China
^*Correspondence e-mail: zhangqh11@126.com

(Received 12 July 2011; accepted 23 July 2011; online 30 July 2011)

In the title compound, C₁₆H₁₆N₂O₅·CH₄O, the two benzene rings in the Schiff base molecule form a dihedral angle of 17.1 (1)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link the components into corrugated sheets parallel to the (101) plane.

Related literature

For the crystal structures of related Schiff base compounds, see: Deng et al. (2009 ); Huang et al. (2008 ). For antibacterial and antitumor activities of Schiff base complexes, see: Brückner et al. (2000 ); Harrop et al. (2003 ); Ren et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₅·CH₄O
M_r = 348.35
Monoclinic, P 2₁ /c
a = 12.467 (3) Å
b = 12.201 (3) Å
c = 11.149 (3) Å
β = 91.191 (3)°
V = 1695.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
8351 measured reflections
2984 independent reflections
1794 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.162
S = 1.00
2984 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O6	0.82	1.92	2.728 (3)	168
O1—H1⋯O5ⁱ	0.82	1.93	2.742 (3)	172
O6—H6⋯O4ⁱⁱ	0.82	2.19	2.973 (4)	161
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029850/cv5134sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029850/cv5134Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029850/cv5134Isup3.cml

checkCIF report

Comment top

Schiff bases containing the C=N fragments arouses considerable interest due to their antifungal, anticancer and antibacterial activities (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). In continuation of our structural studies of Shiff base compounds (Deng et al., 2009; Huang et al., 2008) we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the C7—O5 and C8—N2 bond lengths are 1.228 (3) and 1.274 (3) Å, respecitvely, corresponding to those reported for the related compounds (Deng et al., 2009; Huang et al., 2008). The solvent molecule is linked to the Shiff base molecule via O—H···O hydrogen bond (Table 1).

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link all moieties into corrugated sheets parallel to (101) plane.

Related literature top

For the crystal structures of related Schiff base compounds, see: Deng et al. (2009); Huang et al. (2008). For antibacterial and antitumor activities of Schiff base complexes, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002).

Experimental top

3,5-Dihydroxybenzhydrazide (0.1 mmol,16.8 mg) and 3,4-dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature for 20 minutes and filtered. After keeping the filtrate in air for three days, colourless block-like crystals were formed.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids. Dashed line denotes hydrogen bond.

N'-(3,4-Dimethoxybenzylidene)-3,5-dihydroxybenzohydrazide methanol monosolvate top

Crystal data top

C₁₆H₁₆N₂O₅·CH₄O	F(000) = 736
M_r = 348.35	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1340 reflections
a = 12.467 (3) Å	θ = 2.3–21.1°
b = 12.201 (3) Å	µ = 0.10 mm⁻¹
c = 11.149 (3) Å	T = 295 K
β = 91.191 (3)°	Block, colourless
V = 1695.5 (7) Å³	0.22 × 0.18 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
phi and ω scans	h = −14→11
8351 measured reflections	k = −14→12
2984 independent reflections	l = −12→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0897P)²] where P = (F_o² + 2F_c²)/3
2984 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₅·CH₄O	V = 1695.5 (7) Å³
M_r = 348.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.467 (3) Å	µ = 0.10 mm⁻¹
b = 12.201 (3) Å	T = 295 K
c = 11.149 (3) Å	0.22 × 0.18 × 0.15 mm
β = 91.191 (3)°

Data collection top

Bruker APEXII CCD diffractometer	1794 reflections with I > 2σ(I)
8351 measured reflections	R_int = 0.041
2984 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.68 e Å⁻³
2984 reflections	Δρ_min = −0.32 e Å⁻³
236 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
H18	0.492 (3)	0.340 (3)	0.619 (3)	0.067 (11)*
N2	0.38492 (18)	0.42464 (18)	0.54230 (19)	0.0425 (6)
O5	0.44125 (17)	0.56294 (14)	0.72026 (18)	0.0515 (5)
O1	0.65292 (18)	0.18020 (14)	0.96344 (19)	0.0601 (7)
H1	0.6297	0.1410	0.9091	0.090*
O2	0.70583 (18)	0.55400 (15)	1.06156 (18)	0.0544 (6)
H2	0.7458	0.5258	1.1121	0.082*
N1	0.4573 (2)	0.3984 (2)	0.6318 (2)	0.0430 (6)
C8	0.3653 (2)	0.3502 (2)	0.4648 (2)	0.0421 (7)
H8	0.4011	0.2835	0.4716	0.051*
C9	0.2892 (2)	0.3658 (2)	0.3669 (2)	0.0402 (7)
C4	0.5705 (2)	0.3194 (2)	0.8382 (2)	0.0390 (7)
H4	0.5406	0.2673	0.7867	0.047*
C6	0.5969 (2)	0.5075 (2)	0.8954 (2)	0.0387 (7)
H6A	0.5834	0.5817	0.8830	0.046*
C7	0.4798 (2)	0.4703 (2)	0.7203 (2)	0.0373 (6)
O3	0.10563 (17)	0.57181 (16)	0.23529 (19)	0.0611 (6)
O4	0.06565 (17)	0.41280 (18)	0.09236 (18)	0.0589 (6)
C1	0.6621 (2)	0.4745 (2)	0.9900 (2)	0.0381 (7)
C2	0.6813 (2)	0.3649 (2)	1.0103 (2)	0.0411 (7)
H2A	0.7253	0.3430	1.0743	0.049*
C5	0.5515 (2)	0.43046 (19)	0.8190 (2)	0.0348 (6)
C14	0.2689 (2)	0.2816 (2)	0.2869 (2)	0.0450 (7)
H14	0.3055	0.2156	0.2958	0.054*
C11	0.1620 (2)	0.4774 (2)	0.2587 (2)	0.0423 (7)
C10	0.2352 (2)	0.4653 (2)	0.3514 (2)	0.0411 (7)
H10	0.2488	0.5232	0.4038	0.049*
C12	0.1404 (2)	0.3909 (2)	0.1795 (2)	0.0443 (7)
C3	0.6346 (2)	0.2874 (2)	0.9350 (2)	0.0400 (7)
C13	0.1950 (2)	0.2940 (2)	0.1939 (3)	0.0479 (8)
H13	0.1821	0.2365	0.1409	0.058*
C16	0.0472 (3)	0.3318 (3)	0.0018 (3)	0.0626 (9)
H16A	0.1120	0.3200	−0.0414	0.094*
H16B	−0.0083	0.3565	−0.0527	0.094*
H16C	0.0255	0.2644	0.0386	0.094*
C15	0.1393 (3)	0.6683 (3)	0.2954 (3)	0.0755 (11)
H15A	0.1316	0.6589	0.3803	0.113*
H15B	0.0961	0.7289	0.2684	0.113*
H15C	0.2132	0.6825	0.2783	0.113*
C17	0.8698 (4)	0.4724 (4)	1.3338 (3)	0.0897 (13)
H17A	0.9159	0.5304	1.3616	0.135*
H17B	0.8985	0.4032	1.3598	0.135*
H17C	0.7995	0.4821	1.3658	0.135*
O6	0.8632 (2)	0.4745 (3)	1.2114 (3)	0.1058 (10)
H6	0.9237	0.4726	1.1841	0.159*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0467 (14)	0.0457 (14)	0.0346 (13)	0.0035 (11)	−0.0118 (11)	0.0033 (11)
O5	0.0674 (14)	0.0377 (11)	0.0485 (12)	0.0063 (10)	−0.0173 (10)	0.0032 (9)
O1	0.0853 (17)	0.0318 (11)	0.0617 (14)	0.0043 (10)	−0.0389 (12)	−0.0004 (9)
O2	0.0710 (15)	0.0387 (11)	0.0526 (13)	−0.0065 (10)	−0.0229 (11)	−0.0088 (9)
N1	0.0514 (15)	0.0414 (14)	0.0354 (13)	0.0094 (12)	−0.0155 (11)	−0.0022 (11)
C8	0.0459 (17)	0.0409 (15)	0.0392 (16)	0.0054 (13)	−0.0074 (13)	0.0040 (13)
C9	0.0420 (17)	0.0450 (16)	0.0333 (15)	−0.0011 (13)	−0.0075 (13)	0.0039 (12)
C4	0.0471 (17)	0.0339 (14)	0.0356 (15)	−0.0042 (12)	−0.0097 (13)	−0.0023 (11)
C6	0.0468 (17)	0.0297 (14)	0.0394 (16)	−0.0025 (12)	−0.0043 (13)	0.0010 (12)
C7	0.0410 (16)	0.0354 (15)	0.0355 (15)	0.0004 (12)	−0.0028 (13)	0.0057 (12)
O3	0.0666 (15)	0.0524 (13)	0.0629 (14)	0.0191 (11)	−0.0278 (11)	−0.0073 (10)
O4	0.0559 (13)	0.0718 (14)	0.0479 (12)	0.0096 (11)	−0.0243 (10)	−0.0095 (10)
C1	0.0433 (16)	0.0349 (15)	0.0360 (15)	−0.0068 (12)	−0.0062 (13)	−0.0050 (12)
C2	0.0478 (17)	0.0369 (15)	0.0380 (15)	0.0007 (13)	−0.0156 (13)	−0.0012 (12)
C5	0.0363 (15)	0.0355 (14)	0.0324 (14)	−0.0020 (12)	−0.0049 (12)	0.0033 (11)
C14	0.0537 (18)	0.0400 (15)	0.0409 (16)	0.0041 (14)	−0.0065 (14)	−0.0002 (13)
C11	0.0410 (16)	0.0454 (16)	0.0402 (16)	0.0069 (13)	−0.0064 (13)	0.0011 (13)
C10	0.0430 (16)	0.0439 (16)	0.0361 (15)	0.0023 (13)	−0.0068 (13)	−0.0018 (12)
C12	0.0403 (17)	0.0546 (18)	0.0376 (16)	−0.0019 (14)	−0.0088 (13)	0.0007 (13)
C3	0.0464 (17)	0.0322 (15)	0.0407 (16)	−0.0013 (12)	−0.0113 (13)	0.0009 (12)
C13	0.0561 (19)	0.0460 (17)	0.0412 (17)	−0.0029 (14)	−0.0088 (15)	−0.0047 (13)
C16	0.069 (2)	0.071 (2)	0.0461 (18)	−0.0068 (18)	−0.0232 (17)	−0.0041 (16)
C15	0.091 (3)	0.051 (2)	0.083 (3)	0.0223 (19)	−0.022 (2)	−0.0127 (19)
C17	0.108 (4)	0.100 (3)	0.061 (3)	−0.003 (3)	0.011 (2)	−0.002 (2)
O6	0.077 (2)	0.151 (3)	0.088 (2)	0.007 (2)	−0.0210 (16)	0.011 (2)

Geometric parameters (Å, º) top

N2—C8	1.274 (3)	O4—C16	1.429 (3)
N2—N1	1.370 (3)	C1—C2	1.376 (4)
O5—C7	1.228 (3)	C2—C3	1.384 (4)
O1—C3	1.364 (3)	C2—H2A	0.9300
O1—H1	0.8200	C14—C13	1.381 (4)
O2—C1	1.362 (3)	C14—H14	0.9300
O2—H2	0.8200	C11—C10	1.372 (4)
N1—C7	1.345 (3)	C11—C12	1.399 (4)
N1—H18	0.85 (3)	C10—H10	0.9300
C8—C9	1.443 (4)	C12—C13	1.371 (4)
C8—H8	0.9300	C13—H13	0.9300
C9—C14	1.380 (4)	C16—H16A	0.9600
C9—C10	1.398 (4)	C16—H16B	0.9600
C4—C3	1.385 (4)	C16—H16C	0.9600
C4—C5	1.391 (3)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C6—C1	1.379 (4)	C15—H15C	0.9600
C6—C5	1.382 (3)	C17—O6	1.366 (4)
C6—H6A	0.9300	C17—H17A	0.9600
C7—C5	1.486 (4)	C17—H17B	0.9600
O3—C11	1.371 (3)	C17—H17C	0.9600
O3—C15	1.414 (4)	O6—H6	0.8200
O4—C12	1.360 (3)

C8—N2—N1	116.2 (2)	O3—C11—C10	124.3 (2)
C3—O1—H1	109.5	O3—C11—C12	115.0 (2)
C1—O2—H2	109.5	C10—C11—C12	120.7 (2)
C7—N1—N2	120.4 (2)	C11—C10—C9	119.9 (2)
C7—N1—H18	125 (2)	C11—C10—H10	120.1
N2—N1—H18	114 (2)	C9—C10—H10	120.1
N2—C8—C9	122.2 (3)	O4—C12—C13	125.8 (3)
N2—C8—H8	118.9	O4—C12—C11	115.0 (2)
C9—C8—H8	118.9	C13—C12—C11	119.2 (3)
C14—C9—C10	119.0 (2)	O1—C3—C2	116.6 (2)
C14—C9—C8	120.0 (2)	O1—C3—C4	122.8 (2)
C10—C9—C8	121.0 (2)	C2—C3—C4	120.6 (2)
C3—C4—C5	119.2 (2)	C12—C13—C14	120.3 (3)
C3—C4—H4	120.4	C12—C13—H13	119.9
C5—C4—H4	120.4	C14—C13—H13	119.9
C1—C6—C5	120.0 (2)	O4—C16—H16A	109.5
C1—C6—H6A	120.0	O4—C16—H16B	109.5
C5—C6—H6A	120.0	H16A—C16—H16B	109.5
O5—C7—N1	121.6 (2)	O4—C16—H16C	109.5
O5—C7—C5	122.1 (2)	H16A—C16—H16C	109.5
N1—C7—C5	116.3 (2)	H16B—C16—H16C	109.5
C11—O3—C15	117.6 (2)	O3—C15—H15A	109.5
C12—O4—C16	117.8 (2)	O3—C15—H15B	109.5
O2—C1—C2	122.0 (2)	H15A—C15—H15B	109.5
O2—C1—C6	117.5 (2)	O3—C15—H15C	109.5
C2—C1—C6	120.5 (2)	H15A—C15—H15C	109.5
C1—C2—C3	119.6 (2)	H15B—C15—H15C	109.5
C1—C2—H2A	120.2	O6—C17—H17A	109.5
C3—C2—H2A	120.2	O6—C17—H17B	109.5
C6—C5—C4	120.1 (2)	H17A—C17—H17B	109.5
C6—C5—C7	117.8 (2)	O6—C17—H17C	109.5
C4—C5—C7	122.1 (2)	H17A—C17—H17C	109.5
C9—C14—C13	120.9 (3)	H17B—C17—H17C	109.5
C9—C14—H14	119.5	C17—O6—H6	109.5
C13—C14—H14	119.5

C8—N2—N1—C7	−177.3 (2)	C15—O3—C11—C10	12.5 (4)
N1—N2—C8—C9	178.8 (2)	C15—O3—C11—C12	−167.1 (3)
N2—C8—C9—C14	−178.5 (3)	O3—C11—C10—C9	−179.4 (3)
N2—C8—C9—C10	1.4 (4)	C12—C11—C10—C9	0.2 (4)
N2—N1—C7—O5	−4.0 (4)	C14—C9—C10—C11	1.0 (4)
N2—N1—C7—C5	174.5 (2)	C8—C9—C10—C11	−178.9 (3)
C5—C6—C1—O2	179.2 (2)	C16—O4—C12—C13	−5.1 (4)
C5—C6—C1—C2	−1.0 (4)	C16—O4—C12—C11	174.2 (3)
O2—C1—C2—C3	179.8 (3)	O3—C11—C12—O4	−1.0 (4)
C6—C1—C2—C3	0.1 (4)	C10—C11—C12—O4	179.4 (3)
C1—C6—C5—C4	0.8 (4)	O3—C11—C12—C13	178.3 (3)
C1—C6—C5—C7	178.6 (2)	C10—C11—C12—C13	−1.3 (4)
C3—C4—C5—C6	0.4 (4)	C1—C2—C3—O1	−177.1 (3)
C3—C4—C5—C7	−177.2 (2)	C1—C2—C3—C4	1.2 (4)
O5—C7—C5—C6	−16.5 (4)	C5—C4—C3—O1	176.7 (3)
N1—C7—C5—C6	164.9 (2)	C5—C4—C3—C2	−1.4 (4)
O5—C7—C5—C4	161.2 (3)	O4—C12—C13—C14	−179.6 (3)
N1—C7—C5—C4	−17.4 (4)	C11—C12—C13—C14	1.2 (4)
C10—C9—C14—C13	−1.1 (4)	C9—C14—C13—C12	0.1 (4)
C8—C9—C14—C13	178.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6	0.82	1.92	2.728 (3)	168
O1—H1···O5ⁱ	0.82	1.93	2.742 (3)	172
O6—H6···O4ⁱⁱ	0.82	2.19	2.973 (4)	161

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₅·CH₄O
M_r	348.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.467 (3), 12.201 (3), 11.149 (3)
β (°)	91.191 (3)
V (Å³)	1695.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8351, 2984, 1794
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.162, 1.00
No. of reflections	2984
No. of parameters	236
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6	0.82	1.92	2.728 (3)	167.8
O1—H1···O5ⁱ	0.82	1.93	2.742 (3)	172.0
O6—H6···O4ⁱⁱ	0.82	2.19	2.973 (4)	160.5

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z+1.

Acknowledgements

This project was supported by the Fundamental Research Funds for the Central Universities (project No. CDJRC10220006).

References

Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem. 39, 6100–6106. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deng, S., Han, L., Huang, S., Zhang, H., Diao, Y. & Liu, K. (2009). Acta Cryst. E65, o721. Web of Science CSD CrossRef IUCr Journals Google Scholar
Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. Web of Science CSD CrossRef Google Scholar
Huang, S. S., Diao, Y. P. & Kang, T. G. (2008). Z. Kristallogr. New Cryst. Struct. 223, 167–168. CAS Google Scholar
Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem. 45, 410–419. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 8| August 2011| Page o2189

doi:10.1107/S1600536811029850

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

N′-(3,4-Dimeth­­oxy­benzyl­­idene)-3,5-dihy­dr­oxy­benzohydrazide methanol monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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N′-(3,4-Dimethoxybenzylidene)-3,5-dihydroxybenzohydrazide methanol monosolvate