N'-(5-Bromo-1H-indol-3-ylmethyl-idene)-3,4,5-trihydroxy-benzohydrazide.

The two aromatic parts of the title mol-ecule, C(16)H(12)BrN(3)O(4), are connected through a conjugated -CH=N-NH-C(O)- fragment to furnish an almost planar mol-ecule. Adjacent mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds into a three-dimensional network. An intramolecular O-H⋯O link also occurs.

Related literature

For other Schiff bases derived by condensing 5-bromo-1H-indole-3-carbaldehyde with aroylhydrazines, see: Ali et al. (2005a ▶,b ▶,c ▶).

Experimental

Crystal data

C16H12BrN3O4

M = 390.20

Monoclinic,

a = 9.6454 (2) Å

b = 14.9694 (4) Å

c = 10.3845 (2) Å

β = 97.390 (1)°

V = 1486.92 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.79 mm−1

T = 100 (2) K

0.40 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.401, T max = 0.768

10182 measured reflections

3403 independent reflections

2786 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.02

3403 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.36 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/S1600536808031991/tk2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031991/tk2310Isup2.hkl

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

C16H12BrN3O4	F(000) = 784
Mr = 390.20	Dx = 1.743 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3960 reflections
a = 9.6454 (2) Å	θ = 2.4–28.2°
b = 14.9694 (4) Å	µ = 2.79 mm−1
c = 10.3845 (2) Å	T = 100 K
β = 97.390 (1)°	Block, orange
V = 1486.92 (6) Å3	0.40 × 0.25 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
Tmin = 0.401, Tmax = 0.768	k = −19→19
10182 measured reflections	l = −13→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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.9663P] where P = (Fo2 + 2Fc2)/3
3403 reflections	(Δ/σ)max = 0.003
220 parameters	Δρmax = 0.62 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.

	x	y	z	Uiso*/Ueq
Br1	1.00401 (2)	1.090710 (16)	0.25205 (2)	0.02243 (8)
O1	0.69032 (15)	0.83598 (10)	0.56939 (13)	0.0157 (3)
O2	0.64359 (15)	0.62930 (10)	0.94165 (13)	0.0163 (3)
H2O	0.5987	0.5999	0.9914	0.024*
O3	0.37031 (15)	0.59355 (9)	0.93388 (13)	0.0133 (3)
H3O	0.3085	0.6178	0.9721	0.020*
O4	0.17544 (15)	0.67374 (10)	0.73325 (13)	0.0141 (3)
H4O	0.1569	0.6421	0.7956	0.021*
N1	0.46882 (18)	0.86863 (11)	0.48158 (15)	0.0134 (3)
H1N	0.3788	0.8619	0.4852	0.016*
N2	0.51457 (18)	0.92346 (11)	0.38712 (16)	0.0129 (3)
N3	0.40143 (19)	1.10565 (11)	0.03097 (16)	0.0151 (4)
H3N	0.3557	1.1326	−0.0369	0.018*
C1	0.5056 (2)	0.76400 (13)	0.66032 (18)	0.0123 (4)
C2	0.6012 (2)	0.72451 (13)	0.75620 (18)	0.0129 (4)
H2	0.6984	0.7361	0.7598	0.016*
C3	0.5519 (2)	0.66829 (13)	0.84567 (18)	0.0128 (4)
C4	0.4097 (2)	0.65084 (13)	0.84261 (18)	0.0116 (4)
C5	0.3160 (2)	0.68919 (13)	0.74520 (18)	0.0122 (4)
C6	0.3639 (2)	0.74523 (13)	0.65414 (18)	0.0124 (4)
H6	0.2996	0.7709	0.5873	0.015*
C7	0.5628 (2)	0.82603 (13)	0.56719 (18)	0.0128 (4)
C8	0.4168 (2)	0.96589 (13)	0.31563 (19)	0.0133 (4)
H8	0.3229	0.9587	0.3324	0.016*
C9	0.4446 (2)	1.02350 (13)	0.21187 (19)	0.0125 (4)
C10	0.3424 (2)	1.05580 (14)	0.11812 (19)	0.0150 (4)
H10	0.2451	1.0447	0.1152	0.018*
C11	0.5760 (2)	1.05663 (13)	0.17868 (18)	0.0121 (4)
C12	0.7151 (2)	1.05011 (13)	0.23622 (18)	0.0135 (4)
H12	0.7399	1.0177	0.3144	0.016*
C13	0.8147 (2)	1.09278 (13)	0.1744 (2)	0.0152 (4)
C14	0.7829 (2)	1.14153 (14)	0.0594 (2)	0.0172 (4)
H14	0.8558	1.1685	0.0195	0.021*
C15	0.6456 (2)	1.15045 (14)	0.00394 (19)	0.0158 (4)
H15	0.6215	1.1845	−0.0728	0.019*
C16	0.5443 (2)	1.10761 (13)	0.06493 (19)	0.0138 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.01187 (12)	0.03131 (14)	0.02403 (13)	−0.00169 (9)	0.00198 (8)	0.00285 (9)
O1	0.0119 (7)	0.0181 (7)	0.0178 (7)	−0.0008 (6)	0.0047 (6)	0.0012 (6)
O2	0.0100 (7)	0.0235 (8)	0.0151 (7)	−0.0005 (6)	0.0010 (6)	0.0048 (6)
O3	0.0120 (7)	0.0162 (7)	0.0122 (6)	0.0003 (6)	0.0039 (5)	0.0011 (5)
O4	0.0101 (7)	0.0174 (7)	0.0145 (7)	−0.0035 (6)	0.0005 (5)	0.0038 (5)
N1	0.0114 (9)	0.0144 (8)	0.0152 (8)	−0.0019 (7)	0.0050 (7)	0.0021 (7)
N2	0.0149 (9)	0.0123 (8)	0.0125 (7)	−0.0020 (7)	0.0051 (7)	−0.0006 (6)
N3	0.0158 (9)	0.0156 (9)	0.0133 (8)	0.0028 (7)	−0.0004 (7)	−0.0001 (6)
C1	0.0123 (10)	0.0122 (9)	0.0133 (9)	−0.0012 (8)	0.0044 (7)	−0.0035 (7)
C2	0.0093 (9)	0.0150 (9)	0.0150 (9)	0.0001 (8)	0.0031 (7)	−0.0024 (8)
C3	0.0116 (10)	0.0149 (10)	0.0116 (8)	0.0016 (8)	−0.0002 (7)	−0.0027 (7)
C4	0.0133 (10)	0.0111 (9)	0.0109 (8)	−0.0017 (7)	0.0035 (7)	−0.0017 (7)
C5	0.0101 (9)	0.0126 (9)	0.0143 (9)	−0.0010 (8)	0.0025 (7)	−0.0042 (7)
C6	0.0119 (10)	0.0124 (9)	0.0127 (9)	0.0006 (8)	0.0009 (7)	0.0003 (7)
C7	0.0148 (10)	0.0114 (9)	0.0131 (9)	−0.0005 (8)	0.0046 (8)	−0.0044 (7)
C8	0.0117 (10)	0.0133 (9)	0.0155 (9)	−0.0012 (8)	0.0042 (7)	−0.0031 (8)
C9	0.0131 (10)	0.0104 (9)	0.0141 (9)	0.0005 (8)	0.0018 (8)	−0.0029 (7)
C10	0.0144 (10)	0.0146 (9)	0.0162 (9)	0.0008 (8)	0.0027 (8)	−0.0021 (8)
C11	0.0148 (10)	0.0099 (9)	0.0119 (8)	0.0009 (8)	0.0032 (7)	−0.0025 (7)
C12	0.0165 (10)	0.0125 (9)	0.0116 (9)	0.0023 (8)	0.0028 (7)	−0.0013 (7)
C13	0.0132 (10)	0.0146 (10)	0.0176 (9)	0.0000 (8)	0.0017 (8)	−0.0028 (8)
C14	0.0194 (11)	0.0149 (10)	0.0185 (10)	−0.0026 (9)	0.0072 (8)	−0.0002 (8)
C15	0.0233 (11)	0.0116 (9)	0.0128 (9)	0.0002 (8)	0.0035 (8)	0.0004 (7)
C16	0.0166 (10)	0.0117 (9)	0.0126 (9)	0.0021 (8)	0.0005 (8)	−0.0024 (7)

Br1—C13	1.899 (2)	C2—H2	0.9500
O1—C7	1.236 (3)	C3—C4	1.392 (3)
O2—C3	1.375 (2)	C4—C5	1.391 (3)
O2—H2O	0.8400	C5—C6	1.387 (3)
O3—C4	1.368 (2)	C6—H6	0.9500
O3—H3O	0.8400	C8—C9	1.432 (3)
O4—C5	1.365 (2)	C8—H8	0.9500
O4—H4O	0.8400	C9—C10	1.381 (3)
N1—C7	1.346 (3)	C9—C11	1.443 (3)
N1—N2	1.394 (2)	C10—H10	0.9500
N1—H1N	0.8800	C11—C12	1.401 (3)
N2—C8	1.290 (3)	C11—C16	1.406 (3)
N3—C10	1.354 (3)	C12—C13	1.379 (3)
N3—C16	1.378 (3)	C12—H12	0.9500
N3—H3N	0.8800	C13—C14	1.400 (3)
C1—C6	1.388 (3)	C14—C15	1.381 (3)
C1—C2	1.398 (3)	C14—H14	0.9500
C1—C7	1.497 (3)	C15—C16	1.388 (3)
C2—C3	1.382 (3)	C15—H15	0.9500
C3—O2—H2O	109.5	O1—C7—C1	120.77 (18)
C4—O3—H3O	109.5	N1—C7—C1	116.61 (18)
C5—O4—H4O	109.5	N2—C8—C9	122.40 (19)
C7—N1—N2	119.79 (17)	N2—C8—H8	118.8
C7—N1—H1N	120.1	C9—C8—H8	118.8
N2—N1—H1N	120.1	C10—C9—C8	123.76 (19)
C8—N2—N1	114.89 (17)	C10—C9—C11	106.28 (17)
C10—N3—C16	109.48 (17)	C8—C9—C11	129.92 (19)
C10—N3—H3N	125.3	N3—C10—C9	109.93 (19)
C16—N3—H3N	125.3	N3—C10—H10	125.0
C6—C1—C2	120.15 (18)	C9—C10—H10	125.0
C6—C1—C7	122.57 (18)	C12—C11—C16	119.25 (18)
C2—C1—C7	117.28 (18)	C12—C11—C9	134.17 (18)
C3—C2—C1	118.93 (18)	C16—C11—C9	106.54 (18)
C3—C2—H2	120.5	C13—C12—C11	117.12 (18)
C1—C2—H2	120.5	C13—C12—H12	121.4
O2—C3—C2	120.06 (18)	C11—C12—H12	121.4
O2—C3—C4	118.49 (17)	C12—C13—C14	123.3 (2)
C2—C3—C4	121.44 (18)	C12—C13—Br1	118.96 (15)
O3—C4—C3	117.54 (18)	C14—C13—Br1	117.63 (16)
O3—C4—C5	123.37 (18)	C15—C14—C13	119.95 (19)
C3—C4—C5	119.04 (18)	C15—C14—H14	120.0
O4—C5—C6	117.06 (17)	C13—C14—H14	120.0
O4—C5—C4	122.77 (17)	C14—C15—C16	117.31 (19)
C6—C5—C4	120.17 (19)	C14—C15—H15	121.3
C1—C6—C5	120.23 (18)	C16—C15—H15	121.3
C1—C6—H6	119.9	N3—C16—C15	129.25 (19)
C5—C6—H6	119.9	N3—C16—C11	107.77 (18)
O1—C7—N1	122.61 (18)	C15—C16—C11	122.99 (19)
C7—N1—N2—C8	−175.49 (18)	N2—C8—C9—C10	166.76 (19)
C6—C1—C2—C3	−1.3 (3)	N2—C8—C9—C11	−10.6 (3)
C7—C1—C2—C3	178.65 (17)	C16—N3—C10—C9	0.0 (2)
C1—C2—C3—O2	−179.39 (17)	C8—C9—C10—N3	−177.81 (18)
C1—C2—C3—C4	−0.4 (3)	C11—C9—C10—N3	0.1 (2)
O2—C3—C4—O3	−1.8 (3)	C10—C9—C11—C12	177.6 (2)
C2—C3—C4—O3	179.23 (17)	C8—C9—C11—C12	−4.7 (4)
O2—C3—C4—C5	−179.37 (17)	C10—C9—C11—C16	−0.1 (2)
C2—C3—C4—C5	1.7 (3)	C8—C9—C11—C16	177.60 (19)
O3—C4—C5—O4	0.9 (3)	C16—C11—C12—C13	−1.9 (3)
C3—C4—C5—O4	178.29 (17)	C9—C11—C12—C13	−179.3 (2)
O3—C4—C5—C6	−178.58 (18)	C11—C12—C13—C14	0.2 (3)
C3—C4—C5—C6	−1.2 (3)	C11—C12—C13—Br1	177.22 (14)
C2—C1—C6—C5	1.8 (3)	C12—C13—C14—C15	1.6 (3)
C7—C1—C6—C5	−178.16 (18)	Br1—C13—C14—C15	−175.44 (15)
O4—C5—C6—C1	179.97 (17)	C13—C14—C15—C16	−1.7 (3)
C4—C5—C6—C1	−0.6 (3)	C10—N3—C16—C15	−179.9 (2)
N2—N1—C7—O1	2.9 (3)	C10—N3—C16—C11	0.0 (2)
N2—N1—C7—C1	−176.32 (16)	C14—C15—C16—N3	179.8 (2)
C6—C1—C7—O1	−174.49 (18)	C14—C15—C16—C11	0.0 (3)
C2—C1—C7—O1	5.5 (3)	C12—C11—C16—N3	−178.04 (17)
C6—C1—C7—N1	4.7 (3)	C9—C11—C16—N3	0.1 (2)
C2—C1—C7—N1	−175.23 (17)	C12—C11—C16—C15	1.8 (3)
N1—N2—C8—C9	−178.50 (17)	C9—C11—C16—C15	179.91 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3	0.84	2.21	2.681 (2)	116
O3—H3O···O1i	0.84	1.76	2.595 (2)	173
O4—H4O···N2i	0.84	2.02	2.778 (2)	150
N1—H1N···O2ii	0.88	2.26	3.111 (2)	163
N3—H3N···O4iii	0.88	2.11	2.932 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3	0.84	2.21	2.681 (2)	116
O3—H3O⋯O1i	0.84	1.76	2.595 (2)	173
O4—H4O⋯N2i	0.84	2.02	2.778 (2)	150
N1—H1N⋯O2ii	0.88	2.26	3.111 (2)	163
N3—H3N⋯O4iii	0.88	2.11	2.932 (2)	154

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