N′-(5-Bromo-1H-indol-3-ylmethyl­idene)-3,4,5-trihydroxy­benzohydrazide

Khaledi, H.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808031991

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2108

doi:10.1107/S1600536808031991

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N′-(5-Bromo-1H-indol-3-ylmethylidene)-3,4,5-trihydroxybenzohydrazide

Hamid Khaledi,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 September 2008; accepted 5 October 2008; online 11 October 2008)

The two aromatic parts of the title molecule, C₁₆H₁₂BrN₃O₄, are connected through a conjugated –CH=N—NH—C(O)– fragment to furnish an almost planar molecule. Adjacent molecules 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_r = 390.20
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.02
3403 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808031991/tk2310sup1.cif

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

checkCIF report

Comment top

The molecule of (I), Fig. 1, is almost planar with the aromatic groups connected via a conjugated –CH═N–NH–C(O)– fragment. Molecules are connected into a 3-D network via N—H···O and O—H···O hydrogen bonds, Table 1.

Related literature top

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

Experimental top

5-Bromoindole-3-carbaldehyde (0.34 g, 1.5 mmol) and 3,4,5-trihydroxybenzoylhydrazine (0.27 g, 1.5 mmol) were heated in ethanol (20 ml) for 3 h. About 1 ml of acetic acid also added. The solution was set aside for the growth of crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

N'-(5-Bromo-1H-indol-3-ylmethylidene)-3,4,5- trihydroxybenzohydrazide top

Crystal data top

C₁₆H₁₂BrN₃O₄	F(000) = 784
M_r = 390.20	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	3403 independent reflections
Radiation source: fine-focus sealed tube	2786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.401, T_max = 0.768	k = −19→19
10182 measured reflections	l = −13→13

Refinement top

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(F_o²) + (0.0419P)² + 0.9663P] where P = (F_o² + 2F_c²)/3
3403 reflections	(Δ/σ)_max = 0.003
220 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₆H₁₂BrN₃O₄	V = 1486.92 (6) Å³
M_r = 390.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6454 (2) Å	µ = 2.79 mm⁻¹
b = 14.9694 (4) Å	T = 100 K
c = 10.3845 (2) Å	0.40 × 0.25 × 0.10 mm
β = 97.390 (1)°

Data collection top

Bruker SMART APEX diffractometer	3403 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2786 reflections with I > 2σ(I)
T_min = 0.401, T_max = 0.768	R_int = 0.024
10182 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.02	Δρ_max = 0.62 e Å⁻³
3403 reflections	Δρ_min = −0.36 e Å⁻³
220 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrN₃O₄
M_r	390.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.6454 (2), 14.9694 (4), 10.3845 (2)
β (°)	97.390 (1)
V (Å³)	1486.92 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.79
Crystal size (mm)	0.40 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.401, 0.768
No. of measured, independent and observed [I > 2σ(I)] reflections	10182, 3403, 2786
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.02
No. of reflections	3403
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank the University of Malaya for funding this study (Science Fund Grants 12-02-03-2031, 12-02-03-2051).

References

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