N'-(3,4-Dimeth-oxy-benzyl-idene)-3,5-dihy-droxy-benzohydrazide methanol monosolvate.

In the title compound, C(16)H(16)N(2)O(5)·CH(4)O, the two benzene rings in the Schiff base mol-ecule form a dihedral angle of 17.1 (1)°. In the crystal, inter-molecular 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 = 348.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.162

S = 1.00

2984 reflections

236 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.32 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029850/cv5134sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811029850/cv5134Isup3.cml

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

C16H16N2O5·CH4O	F(000) = 736
Mr = 348.35	Dx = 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

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

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(Fo2) + (0.0897P)2] where P = (Fo2 + 2Fc2)/3
2984 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.32 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
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*

	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)

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)

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.

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) ; (ii) .