(E)-N'-(4-Bromo-benzyl-idene)-3,4-dihydroxy-benzohydrazide monohydrate.

In the title compound, C(14)H(11)BrN(2)O(3)·H(2)O, the dihedral angle between the two benzene rings of the Schiff base is 22.7 (2)° and an intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into layers parallel to the ab plane by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff base compounds from the reaction of aldehydes with primary amines, see: Herrick et al. (2008 ▶); Suresh et al. (2007 ▶). For a related structure, see: Ma et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11BrN2O3·H2O

M = 353.17

Monoclinic,

a = 7.8119 (5) Å

b = 13.8504 (9) Å

c = 13.0764 (9) Å

β = 91.708 (1)°

V = 1414.21 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.92 mm−1

T = 295 K

0.18 × 0.16 × 0.15 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan SADABS (Sheldrick, 1996 ▶) T min = 0.621, T max = 0.668

7384 measured reflections

2511 independent reflections

1810 reflections with I > 2σ(I)

R int = 0.096

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.02

2511 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.69 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036964/hb5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036964/hb5092Isup2.hkl

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

C14H11BrN2O3·H2O	F(000) = 712
Mr = 353.17	Dx = 1.659 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2538 reflections
a = 7.8119 (5) Å	θ = 2.7–24.2°
b = 13.8504 (9) Å	µ = 2.92 mm−1
c = 13.0764 (9) Å	T = 295 K
β = 91.708 (1)°	Block, light yellow
V = 1414.21 (16) Å3	0.18 × 0.16 × 0.15 mm
Z = 4

Siemens SMART CCD diffractometer	2511 independent reflections
Radiation source: fine-focus sealed tube	1810 reflections with I > 2σ(I)
graphite	Rint = 0.096
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −9→9
Tmin = 0.621, Tmax = 0.668	k = −12→16
7384 measured reflections	l = −12→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.053P)2 + 0.0453P] where P = (Fo2 + 2Fc2)/3
2511 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.69 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
Br1	1.08523 (6)	0.16874 (3)	0.20512 (4)	0.0710 (2)
O1	0.2102 (4)	1.04968 (18)	−0.1288 (2)	0.0561 (7)
H1	0.2496	1.0583	−0.1855	0.084*
O2	0.4375 (4)	0.94026 (17)	−0.23369 (19)	0.0590 (8)
H2	0.4882	0.8962	−0.2617	0.089*
O3	0.4997 (3)	0.72271 (16)	0.16417 (17)	0.0439 (6)
O4	0.4061 (3)	0.12989 (17)	0.70360 (19)	0.0500 (7)
H15	0.4361	0.1660	0.7536	0.075*
H16	0.4622	0.0787	0.7172	0.075*
N1	0.5896 (3)	0.66104 (17)	0.0155 (2)	0.0349 (6)
H1A	0.5932	0.6652	−0.0500	0.042*
N2	0.6628 (3)	0.58384 (19)	0.0659 (2)	0.0364 (7)
C1	0.4411 (4)	0.8144 (2)	0.0139 (2)	0.0310 (7)
C2	0.4779 (4)	0.8365 (2)	−0.0866 (3)	0.0343 (8)
H2A	0.5545	0.7982	−0.1215	0.041*
C3	0.4030 (5)	0.9141 (2)	−0.1350 (3)	0.0379 (8)
C4	0.2885 (4)	0.9734 (2)	−0.0836 (3)	0.0375 (8)
C5	0.2535 (4)	0.9517 (2)	0.0159 (3)	0.0435 (9)
H5	0.1770	0.9901	0.0508	0.052*
C6	0.3290 (4)	0.8743 (2)	0.0652 (3)	0.0378 (8)
H6	0.3050	0.8619	0.1331	0.045*
C7	0.5118 (4)	0.7306 (2)	0.0699 (3)	0.0335 (7)
C8	0.7358 (4)	0.5211 (2)	0.0103 (3)	0.0357 (8)
H8	0.7339	0.5285	−0.0604	0.043*
C9	0.8220 (4)	0.4381 (2)	0.0570 (3)	0.0344 (8)
C10	0.8858 (4)	0.3655 (2)	−0.0043 (3)	0.0419 (9)
H10	0.8742	0.3708	−0.0750	0.050*
C11	0.9666 (4)	0.2852 (2)	0.0382 (3)	0.0456 (9)
H11	1.0085	0.2367	−0.0034	0.055*
C12	0.9835 (4)	0.2786 (2)	0.1423 (3)	0.0423 (9)
C13	0.9267 (5)	0.3516 (3)	0.2044 (3)	0.0454 (9)
H13	0.9435	0.3474	0.2750	0.054*
C14	0.8455 (4)	0.4301 (2)	0.1623 (3)	0.0412 (8)
H14	0.8056	0.4786	0.2045	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.0630 (3)	0.0516 (3)	0.0988 (5)	0.02020 (19)	0.0116 (3)	0.0259 (2)
O1	0.0711 (18)	0.0459 (15)	0.0516 (17)	0.0227 (13)	0.0093 (14)	0.0098 (13)
O2	0.114 (2)	0.0323 (13)	0.0316 (14)	0.0185 (14)	0.0206 (14)	0.0067 (11)
O3	0.0707 (16)	0.0354 (13)	0.0260 (14)	0.0040 (11)	0.0064 (12)	−0.0001 (10)
O4	0.0816 (18)	0.0311 (12)	0.0372 (14)	0.0045 (12)	−0.0024 (13)	0.0006 (11)
N1	0.0483 (16)	0.0296 (14)	0.0268 (15)	0.0035 (12)	0.0031 (12)	0.0025 (12)
N2	0.0420 (16)	0.0286 (14)	0.0386 (17)	0.0000 (12)	0.0029 (13)	0.0034 (13)
C1	0.0393 (17)	0.0260 (15)	0.0277 (18)	−0.0034 (13)	0.0021 (14)	−0.0021 (14)
C2	0.0491 (19)	0.0243 (16)	0.0302 (19)	0.0000 (14)	0.0104 (15)	−0.0018 (14)
C3	0.058 (2)	0.0268 (17)	0.0290 (19)	−0.0029 (15)	0.0086 (16)	0.0006 (15)
C4	0.0461 (19)	0.0287 (17)	0.038 (2)	0.0047 (15)	0.0014 (16)	−0.0007 (15)
C5	0.050 (2)	0.040 (2)	0.042 (2)	0.0093 (16)	0.0136 (17)	−0.0038 (17)
C6	0.048 (2)	0.0382 (18)	0.0273 (18)	0.0036 (16)	0.0103 (15)	0.0009 (15)
C7	0.0406 (18)	0.0287 (17)	0.031 (2)	−0.0053 (14)	0.0025 (15)	−0.0014 (15)
C8	0.0424 (18)	0.0322 (18)	0.0326 (19)	−0.0023 (15)	0.0033 (15)	0.0000 (15)
C9	0.0321 (16)	0.0298 (17)	0.042 (2)	−0.0036 (13)	0.0041 (15)	0.0006 (15)
C10	0.046 (2)	0.0390 (19)	0.041 (2)	−0.0008 (16)	0.0039 (17)	−0.0066 (17)
C11	0.0411 (19)	0.0340 (19)	0.062 (3)	0.0026 (15)	0.0049 (18)	−0.0069 (18)
C12	0.0335 (18)	0.0343 (19)	0.059 (3)	0.0005 (14)	0.0078 (17)	0.0066 (18)
C13	0.047 (2)	0.052 (2)	0.037 (2)	0.0060 (17)	0.0031 (17)	0.0067 (18)
C14	0.046 (2)	0.0391 (19)	0.039 (2)	0.0044 (16)	0.0041 (16)	−0.0044 (16)

Br1—C12	1.893 (3)	C3—C4	1.402 (5)
O1—C4	1.348 (4)	C4—C5	1.372 (5)
O1—H1	0.8200	C5—C6	1.374 (5)
O2—C3	1.374 (4)	C5—H5	0.9300
O2—H2	0.8200	C6—H6	0.9300
O3—C7	1.244 (4)	C8—C9	1.458 (5)
O4—H15	0.8499	C8—H8	0.9300
O4—H16	0.8500	C9—C10	1.387 (5)
N1—C7	1.353 (4)	C9—C14	1.387 (5)
N1—N2	1.372 (4)	C10—C11	1.387 (5)
N1—H1A	0.8600	C10—H10	0.9300
N2—C8	1.277 (4)	C11—C12	1.367 (5)
C1—C2	1.387 (5)	C11—H11	0.9300
C1—C6	1.393 (4)	C12—C13	1.378 (5)
C1—C7	1.471 (4)	C13—C14	1.367 (5)
C2—C3	1.369 (5)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300
C4—O1—H1	109.5	O3—C7—N1	120.5 (3)
C3—O2—H2	109.5	O3—C7—C1	121.6 (3)
H15—O4—H16	101.6	N1—C7—C1	117.9 (3)
C7—N1—N2	119.3 (3)	N2—C8—C9	120.4 (3)
C7—N1—H1A	120.3	N2—C8—H8	119.8
N2—N1—H1A	120.3	C9—C8—H8	119.8
C8—N2—N1	116.3 (3)	C10—C9—C14	118.4 (3)
C2—C1—C6	118.4 (3)	C10—C9—C8	119.9 (3)
C2—C1—C7	124.1 (3)	C14—C9—C8	121.6 (3)
C6—C1—C7	117.5 (3)	C11—C10—C9	121.1 (3)
C3—C2—C1	120.9 (3)	C11—C10—H10	119.4
C3—C2—H2A	119.5	C9—C10—H10	119.4
C1—C2—H2A	119.5	C12—C11—C10	118.8 (3)
C2—C3—O2	123.3 (3)	C12—C11—H11	120.6
C2—C3—C4	120.6 (3)	C10—C11—H11	120.6
O2—C3—C4	116.1 (3)	C11—C12—C13	121.0 (3)
O1—C4—C5	119.2 (3)	C11—C12—Br1	120.8 (3)
O1—C4—C3	122.5 (3)	C13—C12—Br1	118.2 (3)
C5—C4—C3	118.3 (3)	C14—C13—C12	119.9 (3)
C4—C5—C6	121.4 (3)	C14—C13—H13	120.0
C4—C5—H5	119.3	C12—C13—H13	120.0
C6—C5—H5	119.3	C13—C14—C9	120.7 (3)
C5—C6—C1	120.4 (3)	C13—C14—H14	119.7
C5—C6—H6	119.8	C9—C14—H14	119.7
C1—C6—H6	119.8
C7—N1—N2—C8	−179.3 (3)	C6—C1—C7—O3	−13.4 (5)
C6—C1—C2—C3	−1.4 (5)	C2—C1—C7—N1	−13.4 (5)
C7—C1—C2—C3	177.9 (3)	C6—C1—C7—N1	165.9 (3)
C1—C2—C3—O2	178.7 (3)	N1—N2—C8—C9	178.0 (3)
C1—C2—C3—C4	0.6 (5)	N2—C8—C9—C10	173.5 (3)
C2—C3—C4—O1	−179.1 (3)	N2—C8—C9—C14	−7.8 (5)
O2—C3—C4—O1	2.7 (5)	C14—C9—C10—C11	2.0 (5)
C2—C3—C4—C5	−0.2 (5)	C8—C9—C10—C11	−179.3 (3)
O2—C3—C4—C5	−178.4 (3)	C9—C10—C11—C12	−0.3 (5)
O1—C4—C5—C6	179.5 (3)	C10—C11—C12—C13	−2.1 (5)
C3—C4—C5—C6	0.5 (5)	C10—C11—C12—Br1	177.7 (2)
C4—C5—C6—C1	−1.4 (5)	C11—C12—C13—C14	2.8 (5)
C2—C1—C6—C5	1.8 (5)	Br1—C12—C13—C14	−177.0 (3)
C7—C1—C6—C5	−177.5 (3)	C12—C13—C14—C9	−1.1 (5)
N2—N1—C7—O3	−3.3 (5)	C10—C9—C14—C13	−1.3 (5)
N2—N1—C7—C1	177.5 (2)	C8—C9—C14—C13	−180.0 (3)
C2—C1—C7—O3	167.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.30	2.734 (3)	114
O4—H16···O2i	0.85	2.03	2.760 (3)	143
O4—H15···O3ii	0.85	1.94	2.761 (3)	163
O2—H2···O3iii	0.82	1.91	2.675 (3)	154
O1—H1···O4iv	0.82	2.16	2.929 (4)	155
N1—H1A···O4v	0.86	2.07	2.898 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.30	2.734 (3)	114
O4—H16⋯O2i	0.85	2.03	2.760 (3)	143
O4—H15⋯O3ii	0.85	1.94	2.761 (3)	163
O2—H2⋯O3iii	0.82	1.91	2.675 (3)	154
O1—H1⋯O4iv	0.82	2.16	2.929 (4)	155
N1—H1A⋯O4v	0.86	2.07	2.898 (4)	162

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