N'-(5-Bromo-2-hydroxy-benzyl-idene)-3,4,5-trihydroxy-benzohydrazide dihydrate.

The title compound, C(14)H(11)BrN(2)O(5)·2H(2)O, crystallizes as hydrogen-bonded sheets. The 2-hydr-oxy group on the benzyl-idene group forms an intra-molecular hydrogen bond to the N atom of the C=N double bond. The amino N atom is a hydrogen-bond donor to a water mol-ecule. The hydr-oxy group on the benzohydrazide group is a hydrogen-bond donor to one acceptor site, whereas each water mol-ecule is a hydrogen-bond donor to two acceptor sites.

Related literature

For the structure of a similar Schiff-base ligand, 5-bromo­salicylaldehyde benzoyl­hydrazone, see: Liu et al. (2006 ▶).

Experimental

Crystal data

C14H11BrN2O5·2H2O

M = 403.19

Monoclinic,

a = 30.8424 (8) Å

b = 3.7999 (1) Å

c = 12.8484 (4) Å

β = 90.280 (2)°

V = 1505.79 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.77 mm−1

T = 100 (2) K

0.30 × 0.03 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.658, T max = 0.921

9964 measured reflections

3424 independent reflections

2914 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.155

S = 1.22

3424 reflections

241 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.08 e Å−3

Δρmin = −1.82 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022708/bt2751sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022708/bt2751Isup2.hkl

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

C14H11BrN2O5·2H2O	F000 = 816
Mr = 403.19	Dx = 1.779 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2758 reflections
a = 30.8424 (8) Å	θ = 3.2–27.4º
b = 3.7999 (1) Å	µ = 2.77 mm−1
c = 12.8484 (4) Å	T = 100 (2) K
β = 90.280 (2)º	Needle, colorless
V = 1505.79 (7) Å3	0.30 × 0.03 × 0.03 mm
Z = 4

Bruker SMART APEX diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2914 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 100(2) K	θmax = 27.5º
ω scans	θmin = 1.3º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −38→40
Tmin = 0.658, Tmax = 0.921	k = −4→4
9964 measured reflections	l = −15→16

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0499P)2 + 10.2476P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max = 0.001
3424 reflections	Δρmax = 1.08 e Å−3
241 parameters	Δρmin = −1.82 e Å−3
10 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Br1	0.467910 (16)	0.31017 (16)	0.89799 (4)	0.01787 (17)
O1	0.32358 (12)	0.6446 (12)	0.5944 (3)	0.0201 (9)
H1O	0.3020 (15)	0.745 (18)	0.621 (5)	0.030*
O2	0.20078 (11)	0.9755 (11)	0.6545 (3)	0.0182 (8)
O3	0.05472 (13)	1.3768 (13)	0.7962 (4)	0.0295 (11)
H3O	0.0335 (16)	1.36 (2)	0.836 (5)	0.044*
O4	0.05208 (14)	1.1036 (15)	0.9894 (4)	0.0353 (12)
H4O	0.048 (3)	0.933 (15)	1.030 (6)	0.053*
O5	0.12324 (12)	0.7692 (12)	1.0737 (3)	0.0182 (9)
H5O	0.1471 (12)	0.682 (18)	1.092 (5)	0.027*
O1W	0.25912 (12)	1.3152 (13)	0.9988 (3)	0.0209 (9)
H1W1	0.2444 (17)	1.382 (18)	1.050 (3)	0.031*
H1W2	0.2806 (14)	1.199 (17)	1.020 (4)	0.031*
O2W	−0.02887 (15)	1.3435 (17)	0.8657 (5)	0.0506 (16)
H2W1	−0.042 (3)	1.30 (2)	0.810 (4)	0.076*
H2W2	−0.038 (3)	1.534 (14)	0.890 (7)	0.076*
N1	0.27850 (13)	0.8683 (12)	0.7531 (3)	0.0139 (9)
N2	0.24174 (13)	0.9859 (13)	0.8027 (3)	0.0138 (9)
H2N	0.2431	1.0511	0.8684	0.017*
C1	0.35563 (16)	0.5778 (15)	0.6648 (4)	0.0144 (10)
C2	0.39381 (16)	0.4251 (16)	0.6295 (4)	0.0173 (11)
H2	0.3970	0.3730	0.5576	0.021*
C3	0.42746 (17)	0.3479 (16)	0.6985 (4)	0.0193 (12)
H3	0.4535	0.2431	0.6743	0.023*
C4	0.42245 (16)	0.4256 (16)	0.8025 (4)	0.0160 (11)
C5	0.38470 (16)	0.5781 (15)	0.8398 (4)	0.0143 (10)
H5	0.3820	0.6294	0.9118	0.017*
C6	0.35065 (15)	0.6562 (15)	0.7712 (4)	0.0126 (10)
C7	0.31105 (16)	0.7988 (15)	0.8138 (4)	0.0130 (10)
H7	0.3089	0.8415	0.8865	0.016*
C8	0.20343 (16)	1.0010 (13)	0.7503 (4)	0.0108 (10)
C9	0.16507 (16)	1.0460 (15)	0.8180 (4)	0.0130 (10)
C10	0.12793 (16)	1.2046 (16)	0.7771 (4)	0.0163 (11)
H10	0.1281	1.2984	0.7086	0.020*
C11	0.09101 (17)	1.2242 (15)	0.8368 (4)	0.0176 (12)
C12	0.09010 (17)	1.0775 (17)	0.9364 (4)	0.0204 (12)
C13	0.12713 (17)	0.9146 (15)	0.9777 (4)	0.0152 (11)
C14	0.16479 (17)	0.9040 (15)	0.9188 (4)	0.0149 (11)
H14	0.1903	0.8006	0.9468	0.018*

	U11	U22	U33	U12	U13	U23
Br1	0.0094 (2)	0.0195 (3)	0.0247 (3)	−0.0001 (2)	−0.00302 (17)	−0.0020 (3)
O1	0.0160 (18)	0.032 (3)	0.0125 (17)	0.0031 (18)	−0.0028 (14)	−0.0016 (17)
O2	0.0127 (17)	0.027 (2)	0.0148 (18)	−0.0039 (16)	−0.0015 (14)	0.0021 (17)
O3	0.0142 (19)	0.041 (3)	0.034 (2)	0.0120 (19)	−0.0051 (17)	−0.005 (2)
O4	0.016 (2)	0.060 (4)	0.030 (2)	0.009 (2)	0.0035 (18)	−0.013 (2)
O5	0.0129 (17)	0.031 (2)	0.0110 (17)	−0.0007 (17)	0.0027 (14)	−0.0045 (16)
O1W	0.0162 (18)	0.035 (2)	0.0113 (17)	0.0027 (18)	0.0015 (14)	−0.0044 (18)
O2W	0.016 (2)	0.049 (4)	0.087 (5)	0.010 (2)	0.010 (2)	0.013 (3)
N1	0.0107 (19)	0.014 (3)	0.017 (2)	−0.0016 (17)	0.0010 (16)	−0.0008 (18)
N2	0.0096 (19)	0.019 (3)	0.013 (2)	−0.0004 (18)	−0.0007 (15)	−0.0028 (18)
C1	0.014 (2)	0.016 (3)	0.014 (2)	−0.002 (2)	−0.0013 (19)	−0.002 (2)
C2	0.013 (2)	0.025 (3)	0.014 (2)	−0.001 (2)	0.0024 (19)	0.000 (2)
C3	0.013 (2)	0.020 (3)	0.025 (3)	0.001 (2)	0.006 (2)	−0.003 (2)
C4	0.012 (2)	0.014 (3)	0.021 (3)	−0.001 (2)	−0.003 (2)	0.003 (2)
C5	0.015 (2)	0.013 (3)	0.015 (2)	−0.001 (2)	0.0005 (19)	−0.002 (2)
C6	0.010 (2)	0.015 (3)	0.013 (2)	−0.003 (2)	0.0008 (18)	0.001 (2)
C7	0.013 (2)	0.015 (3)	0.012 (2)	−0.006 (2)	0.0022 (18)	−0.003 (2)
C8	0.013 (2)	0.004 (3)	0.015 (2)	−0.0007 (18)	−0.0019 (18)	0.0009 (19)
C9	0.011 (2)	0.013 (3)	0.015 (2)	0.000 (2)	−0.0027 (19)	−0.003 (2)
C10	0.013 (2)	0.016 (3)	0.020 (3)	0.001 (2)	−0.0034 (19)	0.000 (2)
C11	0.017 (2)	0.013 (3)	0.022 (3)	0.008 (2)	−0.007 (2)	−0.007 (2)
C12	0.012 (2)	0.027 (3)	0.022 (3)	0.002 (2)	0.001 (2)	−0.012 (2)
C13	0.016 (2)	0.017 (3)	0.013 (2)	0.001 (2)	0.0025 (19)	−0.008 (2)
C14	0.013 (2)	0.016 (3)	0.015 (2)	0.001 (2)	−0.0022 (19)	−0.006 (2)

Br1—C4	1.909 (5)	C1—C6	1.408 (7)
O1—C1	1.361 (6)	C2—C3	1.393 (8)
O1—H1O	0.840 (10)	C2—H2	0.9500
O2—C8	1.236 (6)	C3—C4	1.378 (8)
O3—C11	1.362 (6)	C3—H3	0.9500
O3—H3O	0.838 (10)	C4—C5	1.388 (7)
O4—C12	1.362 (7)	C5—C6	1.400 (7)
O4—H4O	0.840 (10)	C5—H5	0.9500
O5—C13	1.357 (7)	C6—C7	1.446 (7)
O5—H5O	0.841 (10)	C7—H7	0.9500
O1W—H1W1	0.839 (10)	C8—C9	1.482 (7)
O1W—H1W2	0.838 (10)	C9—C10	1.395 (7)
O2W—H2W1	0.838 (10)	C9—C14	1.403 (7)
O2W—H2W2	0.839 (10)	C10—C11	1.378 (7)
N1—C7	1.296 (7)	C10—H10	0.9500
N1—N2	1.378 (6)	C11—C12	1.396 (8)
N2—C8	1.359 (6)	C12—C13	1.401 (8)
N2—H2N	0.8800	C13—C14	1.390 (7)
C1—C2	1.391 (7)	C14—H14	0.9500
C1—O1—H1O	113 (5)	C5—C6—C7	118.3 (4)
C11—O3—H3O	111 (6)	C1—C6—C7	122.9 (5)
C12—O4—H4O	112 (6)	N1—C7—C6	120.1 (4)
C13—O5—H5O	110 (5)	N1—C7—H7	120.0
H1W1—O1W—H1W2	109.6 (18)	C6—C7—H7	120.0
H2W1—O2W—H2W2	109.5 (18)	O2—C8—N2	122.9 (4)
C7—N1—N2	115.1 (4)	O2—C8—C9	123.0 (4)
C8—N2—N1	120.0 (4)	N2—C8—C9	114.1 (4)
C8—N2—H2N	120.0	C10—C9—C14	120.3 (5)
N1—N2—H2N	120.0	C10—C9—C8	119.0 (5)
O1—C1—C2	118.3 (5)	C14—C9—C8	120.4 (5)
O1—C1—C6	121.6 (5)	C11—C10—C9	119.5 (5)
C2—C1—C6	120.1 (5)	C11—C10—H10	120.2
C1—C2—C3	120.6 (5)	C9—C10—H10	120.2
C1—C2—H2	119.7	O3—C11—C10	119.3 (5)
C3—C2—H2	119.7	O3—C11—C12	120.1 (5)
C4—C3—C2	119.1 (5)	C10—C11—C12	120.6 (5)
C4—C3—H3	120.5	O4—C12—C11	116.7 (5)
C2—C3—H3	120.5	O4—C12—C13	123.0 (5)
C3—C4—C5	121.5 (5)	C11—C12—C13	120.3 (5)
C3—C4—Br1	119.2 (4)	O5—C13—C14	124.1 (5)
C5—C4—Br1	119.3 (4)	O5—C13—C12	116.7 (5)
C4—C5—C6	120.0 (5)	C14—C13—C12	119.2 (5)
C4—C5—H5	120.0	C13—C14—C9	120.0 (5)
C6—C5—H5	120.0	C13—C14—H14	120.0
C5—C6—C1	118.7 (5)	C9—C14—H14	120.0
C7—N1—N2—C8	−167.2 (5)	N2—C8—C9—C10	154.0 (5)
O1—C1—C2—C3	−179.3 (5)	O2—C8—C9—C14	147.8 (5)
C6—C1—C2—C3	0.1 (9)	N2—C8—C9—C14	−31.4 (7)
C1—C2—C3—C4	−0.1 (9)	C14—C9—C10—C11	0.6 (9)
C2—C3—C4—C5	0.1 (9)	C8—C9—C10—C11	175.2 (5)
C2—C3—C4—Br1	178.5 (4)	C9—C10—C11—O3	−179.5 (5)
C3—C4—C5—C6	0.0 (9)	C9—C10—C11—C12	−2.0 (9)
Br1—C4—C5—C6	−178.4 (4)	O3—C11—C12—O4	−1.4 (8)
C4—C5—C6—C1	−0.1 (8)	C10—C11—C12—O4	−178.9 (6)
C4—C5—C6—C7	177.0 (5)	O3—C11—C12—C13	178.9 (5)
O1—C1—C6—C5	179.4 (5)	C10—C11—C12—C13	1.4 (9)
C2—C1—C6—C5	0.1 (8)	O4—C12—C13—O5	2.2 (9)
O1—C1—C6—C7	2.5 (9)	C11—C12—C13—O5	−178.1 (5)
C2—C1—C6—C7	−176.9 (5)	O4—C12—C13—C14	−179.1 (6)
N2—N1—C7—C6	176.8 (5)	C11—C12—C13—C14	0.6 (9)
C5—C6—C7—N1	−178.7 (5)	O5—C13—C14—C9	176.7 (5)
C1—C6—C7—N1	−1.8 (8)	C12—C13—C14—C9	−1.9 (8)
N1—N2—C8—O2	−13.6 (8)	C10—C9—C14—C13	1.3 (8)
N1—N2—C8—C9	165.7 (5)	C8—C9—C14—C13	−173.2 (5)
O2—C8—C9—C10	−26.7 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o···O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o···O2wi	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o···O2ii	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1···O2iii	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2···O1ii	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1···O3iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2···O4v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o⋯O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o⋯O2wi	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o⋯O2ii	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1⋯O2iii	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2⋯O1ii	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1⋯O3iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2⋯O4v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)

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