N'-(2-Bromo-5-hy-droxy-4-meth-oxy-benzyl-idene)-3,5-dihy-droxy-benzo-hydrazide methanol monosolvate.

In the crystal structure of the title compound, C(15)H(13)BrN(2)O(5)·CH(3)OH, the methanol solvent mol-ecule links symmetry-related mol-ecules through O-H⋯O and N-H⋯O hydrogen bonds. Further inter-molecular O-H⋯O hydrogen bonds link symmetry-related mol-ecules, leading to the formation of a three-dimensional network. Two of the H atoms involved in hydrogen bonding are disordered. The dihedral angle between the rings is 5.64 (14)°.

Related literature

The title compound is a Schiff base with potential anti­bacterial properties. For the anti­bacterial and anti­tumor activity of Schiff base complexes, see: Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Diao (2007 ▶); Diao et al. (2007 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C15H13BrN2O5·CH4O

M = 413.23

Monoclinic,

a = 7.4242 (17) Å

b = 17.709 (4) Å

c = 12.927 (3) Å

β = 96.493 (3)°

V = 1688.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 296 K

0.47 × 0.24 × 0.19 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.488, T max = 0.616

9884 measured reflections

3780 independent reflections

2569 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.01

3780 reflections

231 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536811008695/kj2170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008695/kj2170Isup2.hkl

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

C15H13BrN2O5·CH4O	F(000) = 840
Mr = 413.23	Dx = 1.625 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2413 reflections
a = 7.4242 (17) Å	θ = 2.3–25.8°
b = 17.709 (4) Å	µ = 2.47 mm−1
c = 12.927 (3) Å	T = 296 K
β = 96.493 (3)°	Block, colorless
V = 1688.7 (6) Å3	0.47 × 0.24 × 0.19 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	2569 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.488, Tmax = 0.616	k = −14→22
9884 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.8829P] where P = (Fo2 + 2Fc2)/3
3780 reflections	(Δ/σ)max = 0.001
231 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.36 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	Occ. (<1)
Br1	0.38821 (6)	0.687078 (19)	0.54748 (3)	0.05529 (16)
O1	0.6149 (3)	0.58020 (13)	0.91725 (17)	0.0527 (6)
O2	0.5254 (4)	0.43891 (13)	0.86339 (18)	0.0652 (8)
H2A	0.6165	0.4422	0.9054	0.098*	0.50
H2B	0.4884	0.4338	0.9204	0.098*	0.50
O3	0.1127 (4)	0.31210 (12)	0.42579 (17)	0.0541 (7)
O4	−0.2407 (4)	0.19793 (12)	0.12235 (16)	0.0501 (6)
H4A	−0.2804	0.1933	0.0609	0.075*
O5	−0.1488 (4)	0.45108 (14)	0.01335 (18)	0.0636 (8)
H5A	−0.0942	0.4914	0.0180	0.095*	0.50
H5B	−0.2327	0.4458	−0.0330	0.095*	0.50
N1	0.2142 (3)	0.44876 (14)	0.49680 (17)	0.0348 (6)
N2	0.1270 (3)	0.43712 (14)	0.39748 (18)	0.0354 (6)
H2	0.1071	0.4774	0.3608	0.059 (11)*
C1	0.3706 (4)	0.53397 (16)	0.6178 (2)	0.0314 (7)
C2	0.4255 (4)	0.60688 (16)	0.6447 (2)	0.0327 (7)
C3	0.5083 (4)	0.62529 (17)	0.7431 (2)	0.0370 (7)
H3A	0.5428	0.6748	0.7590	0.044*
C4	0.5387 (4)	0.56937 (17)	0.8169 (2)	0.0373 (7)
C5	0.4914 (5)	0.49492 (17)	0.7916 (2)	0.0394 (8)
C6	0.4093 (4)	0.47768 (17)	0.6937 (2)	0.0367 (7)
H6A	0.3787	0.4278	0.6774	0.044*
C7	−0.0144 (4)	0.35570 (16)	0.2601 (2)	0.0311 (7)
C8	−0.0809 (4)	0.28403 (17)	0.2367 (2)	0.0343 (7)
H8A	−0.0643	0.2459	0.2863	0.041*
C9	−0.1723 (4)	0.26884 (16)	0.1392 (2)	0.0323 (7)
C10	−0.1920 (4)	0.32480 (16)	0.0639 (2)	0.0326 (7)
H10A	−0.2497	0.3146	−0.0023	0.039*
C11	−0.1249 (4)	0.39546 (17)	0.0888 (2)	0.0369 (7)
C12	−0.0367 (4)	0.41262 (16)	0.1864 (2)	0.0345 (7)
H12A	0.0062	0.4611	0.2019	0.041*
C13	0.6728 (5)	0.6544 (2)	0.9486 (3)	0.0553 (10)
H13A	0.7628	0.6715	0.9062	0.083*
H13B	0.7237	0.6536	1.0203	0.083*
H13C	0.5710	0.6882	0.9406	0.083*
C14	0.2758 (4)	0.51463 (17)	0.5154 (2)	0.0350 (7)
H14A	0.2607	0.5512	0.4636	0.042*
C15	0.0798 (4)	0.36657 (17)	0.3681 (2)	0.0329 (7)
O6	0.0298 (5)	0.58875 (17)	0.3072 (3)	0.0832 (9)
H6	−0.0533	0.6068	0.3359	0.125*
C16	0.0995 (12)	0.6427 (4)	0.2480 (5)	0.156 (4)
H16A	0.0079	0.6588	0.1942	0.234*
H16B	0.2005	0.6222	0.2171	0.234*
H16C	0.1391	0.6850	0.2911	0.234*

	U11	U22	U33	U12	U13	U23
Br1	0.0774 (3)	0.0372 (2)	0.0484 (2)	−0.00523 (18)	−0.00500 (17)	0.01134 (15)
O1	0.0713 (17)	0.0449 (14)	0.0359 (12)	−0.0053 (12)	−0.0200 (11)	−0.0098 (10)
O2	0.103 (2)	0.0426 (14)	0.0412 (13)	−0.0058 (14)	−0.0278 (13)	0.0078 (11)
O3	0.0851 (19)	0.0325 (12)	0.0368 (12)	−0.0003 (12)	−0.0268 (12)	0.0045 (10)
O4	0.0834 (19)	0.0339 (13)	0.0286 (11)	−0.0130 (11)	−0.0126 (12)	−0.0003 (9)
O5	0.094 (2)	0.0457 (15)	0.0418 (13)	−0.0179 (13)	−0.0316 (13)	0.0206 (11)
N1	0.0415 (15)	0.0358 (14)	0.0241 (12)	0.0030 (12)	−0.0085 (11)	−0.0049 (10)
N2	0.0475 (16)	0.0300 (13)	0.0255 (12)	0.0015 (11)	−0.0101 (11)	−0.0012 (11)
C1	0.0342 (17)	0.0315 (16)	0.0276 (14)	−0.0011 (12)	0.0001 (12)	−0.0036 (12)
C2	0.0336 (17)	0.0299 (15)	0.0343 (15)	0.0019 (13)	0.0024 (13)	0.0029 (12)
C3	0.0408 (19)	0.0288 (16)	0.0398 (17)	−0.0038 (13)	−0.0030 (14)	−0.0074 (13)
C4	0.0387 (19)	0.0387 (17)	0.0320 (16)	0.0009 (14)	−0.0075 (13)	−0.0084 (13)
C5	0.052 (2)	0.0307 (16)	0.0328 (16)	0.0003 (14)	−0.0086 (14)	−0.0008 (13)
C6	0.0444 (19)	0.0268 (15)	0.0365 (16)	−0.0030 (13)	−0.0058 (14)	−0.0042 (12)
C7	0.0333 (17)	0.0329 (16)	0.0250 (14)	0.0037 (13)	−0.0058 (12)	−0.0037 (12)
C8	0.0463 (19)	0.0302 (15)	0.0244 (14)	0.0036 (13)	−0.0050 (13)	0.0011 (12)
C9	0.0408 (19)	0.0263 (15)	0.0286 (15)	0.0003 (13)	−0.0015 (13)	−0.0041 (12)
C10	0.0369 (17)	0.0381 (17)	0.0205 (13)	−0.0013 (13)	−0.0065 (12)	0.0003 (12)
C11	0.0421 (19)	0.0345 (17)	0.0315 (15)	−0.0014 (14)	−0.0074 (13)	0.0074 (13)
C12	0.0417 (18)	0.0279 (15)	0.0306 (15)	−0.0030 (13)	−0.0101 (13)	−0.0007 (12)
C13	0.058 (2)	0.050 (2)	0.054 (2)	−0.0051 (18)	−0.0111 (18)	−0.0216 (18)
C14	0.0421 (19)	0.0341 (16)	0.0273 (15)	−0.0006 (14)	−0.0020 (13)	−0.0013 (12)
C15	0.0357 (18)	0.0360 (16)	0.0251 (14)	0.0019 (13)	−0.0052 (12)	−0.0031 (12)
O6	0.093 (3)	0.0608 (19)	0.095 (2)	0.0126 (16)	0.0061 (19)	0.0034 (17)
C16	0.276 (10)	0.091 (5)	0.119 (5)	0.061 (5)	0.094 (6)	0.051 (4)

Br1—C2	1.896 (3)	C4—C5	1.394 (4)
O1—C4	1.368 (3)	C5—C6	1.375 (4)
O1—C13	1.428 (4)	C6—H6A	0.9300
O2—C5	1.362 (4)	C7—C8	1.383 (4)
O2—H2A	0.8200	C7—C12	1.384 (4)
O2—H2B	0.8200	C7—C15	1.501 (4)
O3—C15	1.227 (3)	C8—C9	1.388 (4)
O4—C9	1.363 (3)	C8—H8A	0.9300
O4—H4A	0.8200	C9—C10	1.385 (4)
O5—C11	1.383 (3)	C10—C11	1.372 (4)
O5—H5A	0.8200	C10—H10A	0.9300
O5—H5B	0.8200	C11—C12	1.388 (4)
N1—C14	1.266 (4)	C12—H12A	0.9300
N1—N2	1.386 (3)	C13—H13A	0.9600
N2—C15	1.341 (4)	C13—H13B	0.9600
N2—H2	0.8600	C13—H13C	0.9600
C1—C2	1.386 (4)	C14—H14A	0.9300
C1—C6	1.405 (4)	O6—C16	1.362 (6)
C1—C14	1.468 (4)	O6—H6	0.8200
C2—C3	1.388 (4)	C16—H16A	0.9600
C3—C4	1.376 (4)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—O1—C13	118.5 (3)	C7—C8—H8A	119.9
C5—O2—H2A	118.4	C9—C8—H8A	119.9
C5—O2—H2B	129.6	O4—C9—C10	122.6 (3)
H2A—O2—H2B	75.4	O4—C9—C8	117.3 (2)
C9—O4—H4A	109.5	C10—C9—C8	120.1 (3)
C11—O5—H5A	123.0	C11—C10—C9	118.8 (3)
C11—O5—H5B	117.4	C11—C10—H10A	120.6
H5A—O5—H5B	118.8	C9—C10—H10A	120.6
C14—N1—N2	115.7 (2)	C10—C11—O5	118.0 (3)
C15—N2—N1	118.7 (2)	C10—C11—C12	122.3 (3)
C15—N2—H2	126.4	O5—C11—C12	119.7 (3)
N1—N2—H2	114.8	C7—C12—C11	118.3 (3)
C2—C1—C6	117.1 (3)	C7—C12—H12A	120.9
C2—C1—C14	122.7 (3)	C11—C12—H12A	120.9
C6—C1—C14	120.2 (3)	O1—C13—H13A	109.5
C1—C2—C3	122.4 (3)	O1—C13—H13B	109.5
C1—C2—Br1	121.0 (2)	H13A—C13—H13B	109.5
C3—C2—Br1	116.6 (2)	O1—C13—H13C	109.5
C4—C3—C2	119.2 (3)	H13A—C13—H13C	109.5
C4—C3—H3A	120.4	H13B—C13—H13C	109.5
C2—C3—H3A	120.4	N1—C14—C1	120.8 (3)
O1—C4—C3	125.0 (3)	N1—C14—H14A	119.6
O1—C4—C5	114.9 (3)	C1—C14—H14A	119.6
C3—C4—C5	120.0 (3)	O3—C15—N2	122.2 (3)
O2—C5—C6	119.6 (3)	O3—C15—C7	120.3 (3)
O2—C5—C4	120.4 (3)	N2—C15—C7	117.5 (2)
C6—C5—C4	120.0 (3)	C16—O6—H6	109.5
C5—C6—C1	121.3 (3)	O6—C16—H16A	109.5
C5—C6—H6A	119.4	O6—C16—H16B	109.5
C1—C6—H6A	119.4	H16A—C16—H16B	109.5
C8—C7—C12	120.4 (2)	O6—C16—H16C	109.5
C8—C7—C15	116.0 (2)	H16A—C16—H16C	109.5
C12—C7—C15	123.6 (3)	H16B—C16—H16C	109.5
C7—C8—C9	120.2 (3)
C14—N1—N2—C15	171.4 (3)	C15—C7—C8—C9	179.1 (3)
C6—C1—C2—C3	−2.7 (5)	C7—C8—C9—O4	−177.4 (3)
C14—C1—C2—C3	177.2 (3)	C7—C8—C9—C10	2.1 (5)
C6—C1—C2—Br1	177.9 (2)	O4—C9—C10—C11	177.5 (3)
C14—C1—C2—Br1	−2.2 (4)	C8—C9—C10—C11	−2.0 (5)
C1—C2—C3—C4	0.5 (5)	C9—C10—C11—O5	−178.8 (3)
Br1—C2—C3—C4	179.9 (2)	C9—C10—C11—C12	0.5 (5)
C13—O1—C4—C3	−1.8 (5)	C8—C7—C12—C11	−0.8 (5)
C13—O1—C4—C5	177.9 (3)	C15—C7—C12—C11	179.4 (3)
C2—C3—C4—O1	−178.4 (3)	C10—C11—C12—C7	0.9 (5)
C2—C3—C4—C5	1.9 (5)	O5—C11—C12—C7	−179.8 (3)
O1—C4—C5—O2	−1.5 (5)	N2—N1—C14—C1	179.9 (3)
C3—C4—C5—O2	178.3 (3)	C2—C1—C14—N1	−173.9 (3)
O1—C4—C5—C6	178.3 (3)	C6—C1—C14—N1	5.9 (5)
C3—C4—C5—C6	−2.0 (5)	N1—N2—C15—O3	−0.7 (5)
O2—C5—C6—C1	179.5 (3)	N1—N2—C15—C7	−180.0 (3)
C4—C5—C6—C1	−0.3 (5)	C8—C7—C15—O3	8.3 (4)
C2—C1—C6—C5	2.5 (5)	C12—C7—C15—O3	−171.9 (3)
C14—C1—C6—C5	−177.3 (3)	C8—C7—C15—N2	−172.4 (3)
C12—C7—C8—C9	−0.7 (5)	C12—C7—C15—N2	7.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O5i	0.82	2.11	2.932 (3)	180
O2—H2B···O1ii	0.82	2.33	3.148 (4)	180
O4—H4A···O3iii	0.82	1.84	2.655 (3)	175
O5—H5A···O5iv	0.82	2.15	2.859 (5)	145
O5—H5B···O2v	0.82	2.12	2.932 (3)	171
N2—H2···O6	0.86	2.15	2.984 (4)	164
O6—H6···O4vi	0.82	2.33	3.101 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O5i	0.82	2.11	2.932 (3)	180
O2—H2B⋯O1ii	0.82	2.33	3.148 (4)	180
O4—H4A⋯O3iii	0.82	1.84	2.655 (3)	175
O5—H5A⋯O5iv	0.82	2.15	2.859 (5)	145
O5—H5B⋯O2v	0.82	2.12	2.932 (3)	171
N2—H2⋯O6	0.86	2.15	2.984 (4)	164
O6—H6⋯O4vi	0.82	2.33	3.101 (4)	157

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .