N′-(3-Bromo-5-chloro-2-hydroxy­benzyl­idine)-2-hydroxy­benzohydrazide

Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536808038634

organic compounds

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Volume 64| Part 12| December 2008| Page o2438

doi:10.1107/S1600536808038634

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N′-(3-Bromo-5-chloro-2-hydroxybenzylidine)-2-hydroxybenzohydrazide

Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah A. Rahman ^a and Seik Weng Ng ^a ^*

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

(Received 18 November 2008; accepted 19 November 2008; online 26 November 2008)

In the approximately planar title molecule, C₁₄H₁₀BrClN₃O₂, the dihedral angle between the aromatic ring planes is 5.79 (12)°. The conformation is stabilized by intramolecular O—H⋯N and N—H⋯O hydrogen bonds and an intermolecular O—H⋯O link leads to chains in the crystal propagating in [001].

Related literature

For similar Schiff bases, see: Hu et al. (2005 ); Wu et al. (2006 ); Yehye et al. (2008a ,b ).

Experimental

Crystal data

C₁₄H₁₀BrClN₂O₃
M_r = 369.60
Monoclinic, P 2₁ /c
a = 15.8387 (3) Å
b = 6.9319 (1) Å
c = 12.9951 (3) Å
β = 106.461 (1)°
V = 1368.28 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.21 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.446, T_max = 0.856
12350 measured reflections
3136 independent reflections
2545 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.077
S = 1.02
3136 reflections
202 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2ⁱ	0.83 (1)	1.76 (1)	2.591 (2)	175 (3)
O3—H3o⋯N2	0.84 (1)	1.88 (2)	2.632 (3)	149 (3)
N1—H1n⋯O1	0.87 (1)	1.90 (2)	2.614 (3)	139 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808038634/hb2857sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038634/hb2857Isup2.hkl

checkCIF report

Comment top

In the approximately planar title molecule, (I), (Fig. 1) the dihedral angle between the aromatic ring planes is 5.79 (12)°. The conformation is stabilised by intramolecular O—H···N and N—H···O hydrogen bonds and an intermolecular O—H···O link leads to chains in the crystal (Table 1).

Related literature top

For similar Schiff bases, see: Hu et al. (2005); Wu et al. (2006); Yehye et al. (2008a,b).

Experimental top

2-Hydroxybenzohydrazide(0.60 g, 4 mmol) and 3-bromo-5-chloro-2-ydroxybenzaldehyde (0.94 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the resulting solid was recrystallized from ethanol to yield yellow plates of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (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. The molecular structure of (I) with atoms shown at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.

N'-(3-Bromo-5-chloro-2-hydroxybenzylidine)-2-hydroxybenzohydrazide top

Crystal data top

C₁₄H₁₀BrClN₂O₃	F(000) = 736
M_r = 369.60	D_x = 1.794 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3691 reflections
a = 15.8387 (3) Å	θ = 3.2–28.2°
b = 6.9319 (1) Å	µ = 3.21 mm⁻¹
c = 12.9951 (3) Å	T = 100 K
β = 106.461 (1)°	Plate, yellow
V = 1368.28 (5) Å³	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	3136 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.446, T_max = 0.856	k = −9→8
12350 measured reflections	l = −16→16

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: difmap and geom
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0353P)² + 1.3959P] where P = (F_o² + 2F_c²)/3
3136 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.43 e Å⁻³
3 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₀BrClN₂O₃	V = 1368.28 (5) Å³
M_r = 369.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8387 (3) Å	µ = 3.21 mm⁻¹
b = 6.9319 (1) Å	T = 100 K
c = 12.9951 (3) Å	0.30 × 0.20 × 0.05 mm
β = 106.461 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3136 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2545 reflections with I > 2σ(I)
T_min = 0.446, T_max = 0.856	R_int = 0.038
12350 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	3 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.43 e Å⁻³
3136 reflections	Δρ_min = −0.41 e Å⁻³
202 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	0.145097 (18)	0.43521 (4)	0.04463 (2)	0.02196 (9)
Cl1	−0.04591 (4)	0.45367 (9)	0.33930 (5)	0.01932 (14)
O1	0.48671 (11)	0.8436 (3)	0.72174 (14)	0.0186 (4)
H1O	0.495 (2)	0.837 (5)	0.7879 (9)	0.033 (9)*
O2	0.52114 (12)	0.6952 (3)	0.42779 (14)	0.0224 (4)
O3	0.28679 (12)	0.5844 (3)	0.23371 (14)	0.0184 (4)
H3O	0.3254 (15)	0.616 (4)	0.2897 (15)	0.027 (9)*
N1	0.42237 (13)	0.7471 (3)	0.52022 (16)	0.0142 (4)
H1N	0.4157 (17)	0.778 (4)	0.5825 (12)	0.015 (7)*
N2	0.35545 (13)	0.6804 (3)	0.43620 (16)	0.0154 (4)
C1	0.56768 (15)	0.8577 (4)	0.70555 (19)	0.0140 (5)
C2	0.64075 (16)	0.9151 (4)	0.7881 (2)	0.0163 (5)
H2	0.6343	0.9445	0.8569	0.020*
C3	0.72242 (16)	0.9295 (4)	0.7702 (2)	0.0171 (5)
H3	0.7720	0.9670	0.8271	0.021*
C4	0.73279 (16)	0.8897 (4)	0.6701 (2)	0.0174 (5)
H4	0.7890	0.9010	0.6581	0.021*
C5	0.66035 (16)	0.8333 (4)	0.5875 (2)	0.0158 (5)
H5	0.6674	0.8061	0.5187	0.019*
C6	0.57684 (15)	0.8157 (3)	0.60395 (19)	0.0131 (5)
C7	0.50521 (16)	0.7480 (3)	0.51062 (19)	0.0149 (5)
C8	0.27901 (16)	0.6691 (4)	0.4507 (2)	0.0154 (5)
H8	0.2706	0.7070	0.5174	0.018*
C9	0.20470 (16)	0.5978 (3)	0.3648 (2)	0.0155 (5)
C10	0.21190 (16)	0.5580 (3)	0.2611 (2)	0.0153 (5)
C11	0.13777 (17)	0.4882 (4)	0.1845 (2)	0.0162 (5)
C12	0.05895 (16)	0.4549 (3)	0.2073 (2)	0.0169 (5)
H12	0.0095	0.4062	0.1538	0.020*
C13	0.05363 (16)	0.4941 (4)	0.3096 (2)	0.0163 (5)
C14	0.12487 (17)	0.5652 (3)	0.3880 (2)	0.0171 (5)
H14	0.1197	0.5921	0.4577	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02322 (15)	0.02735 (15)	0.01301 (13)	−0.00167 (11)	0.00141 (10)	−0.00143 (11)
Cl1	0.0119 (3)	0.0207 (3)	0.0259 (3)	−0.0026 (2)	0.0063 (2)	−0.0016 (3)
O1	0.0127 (9)	0.0334 (10)	0.0096 (8)	−0.0027 (8)	0.0032 (7)	−0.0009 (8)
O2	0.0184 (9)	0.0369 (11)	0.0111 (9)	0.0009 (8)	0.0027 (7)	−0.0044 (8)
O3	0.0149 (9)	0.0247 (10)	0.0149 (9)	−0.0035 (7)	0.0029 (7)	−0.0025 (8)
N1	0.0129 (10)	0.0201 (11)	0.0079 (10)	−0.0002 (8)	0.0000 (8)	−0.0028 (8)
N2	0.0148 (10)	0.0162 (10)	0.0113 (10)	0.0002 (8)	−0.0027 (8)	−0.0009 (8)
C1	0.0124 (12)	0.0151 (12)	0.0136 (12)	0.0003 (9)	0.0020 (9)	0.0018 (10)
C2	0.0162 (12)	0.0192 (12)	0.0122 (12)	−0.0016 (10)	0.0018 (10)	−0.0003 (10)
C3	0.0131 (12)	0.0181 (12)	0.0176 (12)	−0.0002 (10)	0.0000 (10)	0.0005 (11)
C4	0.0127 (12)	0.0188 (13)	0.0209 (13)	0.0007 (10)	0.0052 (10)	0.0017 (10)
C5	0.0167 (12)	0.0163 (12)	0.0150 (12)	0.0017 (10)	0.0054 (10)	0.0012 (10)
C6	0.0137 (11)	0.0127 (11)	0.0113 (11)	0.0010 (9)	0.0008 (9)	0.0021 (9)
C7	0.0168 (12)	0.0151 (11)	0.0116 (12)	0.0017 (10)	0.0018 (10)	0.0028 (10)
C8	0.0170 (12)	0.0144 (12)	0.0124 (11)	0.0013 (10)	0.0005 (10)	−0.0014 (10)
C9	0.0140 (12)	0.0147 (12)	0.0157 (12)	0.0005 (9)	0.0009 (10)	−0.0004 (10)
C10	0.0144 (12)	0.0133 (12)	0.0177 (12)	0.0022 (9)	0.0038 (10)	0.0040 (10)
C11	0.0185 (13)	0.0147 (11)	0.0132 (12)	0.0014 (10)	0.0011 (10)	0.0004 (10)
C12	0.0140 (12)	0.0152 (12)	0.0175 (13)	−0.0008 (10)	−0.0021 (10)	−0.0002 (10)
C13	0.0126 (12)	0.0132 (11)	0.0224 (13)	0.0007 (9)	0.0038 (10)	0.0010 (10)
C14	0.0188 (12)	0.0150 (12)	0.0166 (12)	0.0020 (10)	0.0037 (10)	0.0003 (10)

Geometric parameters (Å, º) top

Br1—C11	1.890 (3)	C3—H3	0.9500
Cl1—C13	1.749 (3)	C4—C5	1.387 (4)
O1—C1	1.361 (3)	C4—H4	0.9500
O1—H1O	0.833 (10)	C5—C6	1.404 (3)
O2—C7	1.229 (3)	C5—H5	0.9500
O3—C10	1.344 (3)	C6—C7	1.483 (3)
O3—H3O	0.836 (10)	C8—C9	1.459 (3)
N1—C7	1.353 (3)	C8—H8	0.9500
N1—N2	1.369 (3)	C9—C14	1.399 (4)
N1—H1N	0.872 (10)	C9—C10	1.412 (4)
N2—C8	1.279 (3)	C10—C11	1.393 (3)
C1—C2	1.395 (3)	C11—C12	1.382 (4)
C1—C6	1.399 (3)	C12—C13	1.383 (4)
C2—C3	1.382 (4)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.379 (4)
C3—C4	1.384 (4)	C14—H14	0.9500

C1—O1—H1O	106 (2)	O2—C7—N1	121.6 (2)
C10—O3—H3O	107 (2)	O2—C7—C6	120.8 (2)
C7—N1—N2	118.7 (2)	N1—C7—C6	117.6 (2)
C7—N1—H1N	117.4 (18)	N2—C8—C9	120.0 (2)
N2—N1—H1N	123.5 (18)	N2—C8—H8	120.0
C8—N2—N1	117.0 (2)	C9—C8—H8	120.0
O1—C1—C2	121.0 (2)	C14—C9—C10	119.8 (2)
O1—C1—C6	119.0 (2)	C14—C9—C8	118.2 (2)
C2—C1—C6	120.0 (2)	C10—C9—C8	122.0 (2)
C3—C2—C1	120.2 (2)	O3—C10—C11	119.1 (2)
C3—C2—H2	119.9	O3—C10—C9	122.8 (2)
C1—C2—H2	119.9	C11—C10—C9	118.0 (2)
C2—C3—C4	120.7 (2)	C12—C11—C10	122.3 (2)
C2—C3—H3	119.6	C12—C11—Br1	118.63 (19)
C4—C3—H3	119.6	C10—C11—Br1	119.05 (19)
C3—C4—C5	119.4 (2)	C11—C12—C13	118.6 (2)
C3—C4—H4	120.3	C11—C12—H12	120.7
C5—C4—H4	120.3	C13—C12—H12	120.7
C4—C5—C6	121.0 (2)	C14—C13—C12	121.3 (2)
C4—C5—H5	119.5	C14—C13—Cl1	119.6 (2)
C6—C5—H5	119.5	C12—C13—Cl1	119.01 (19)
C1—C6—C5	118.7 (2)	C13—C14—C9	119.9 (2)
C1—C6—C7	125.3 (2)	C13—C14—H14	120.0
C5—C6—C7	116.0 (2)	C9—C14—H14	120.0

C7—N1—N2—C8	175.3 (2)	N2—C8—C9—C14	172.3 (2)
O1—C1—C2—C3	−179.7 (2)	N2—C8—C9—C10	−6.4 (4)
C6—C1—C2—C3	−0.5 (4)	C14—C9—C10—O3	−179.4 (2)
C1—C2—C3—C4	0.8 (4)	C8—C9—C10—O3	−0.7 (4)
C2—C3—C4—C5	−0.6 (4)	C14—C9—C10—C11	0.5 (4)
C3—C4—C5—C6	−0.1 (4)	C8—C9—C10—C11	179.2 (2)
O1—C1—C6—C5	179.1 (2)	O3—C10—C11—C12	179.1 (2)
C2—C1—C6—C5	−0.2 (4)	C9—C10—C11—C12	−0.9 (4)
O1—C1—C6—C7	−2.6 (4)	O3—C10—C11—Br1	−0.5 (3)
C2—C1—C6—C7	178.1 (2)	C9—C10—C11—Br1	179.55 (18)
C4—C5—C6—C1	0.4 (4)	C10—C11—C12—C13	0.6 (4)
C4—C5—C6—C7	−178.0 (2)	Br1—C11—C12—C13	−179.88 (18)
N2—N1—C7—O2	1.8 (4)	C11—C12—C13—C14	0.1 (4)
N2—N1—C7—C6	−178.3 (2)	C11—C12—C13—Cl1	179.70 (19)
C1—C6—C7—O2	−172.2 (2)	C12—C13—C14—C9	−0.5 (4)
C5—C6—C7—O2	6.1 (3)	Cl1—C13—C14—C9	179.98 (18)
C1—C6—C7—N1	7.9 (4)	C10—C9—C14—C13	0.1 (4)
C5—C6—C7—N1	−173.8 (2)	C8—C9—C14—C13	−178.6 (2)
N1—N2—C8—C9	−179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2ⁱ	0.83 (1)	1.76 (1)	2.591 (2)	175 (3)
O3—H3o···N2	0.84 (1)	1.88 (2)	2.632 (3)	149 (3)
N1—H1n···O1	0.87 (1)	1.90 (2)	2.614 (3)	139 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrClN₂O₃
M_r	369.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.8387 (3), 6.9319 (1), 12.9951 (3)
β (°)	106.461 (1)
V (Å³)	1368.28 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.21
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.446, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections	12350, 3136, 2545
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.02
No. of reflections	3136
No. of parameters	202
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.41

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
O1—H1o···O2ⁱ	0.83 (1)	1.76 (1)	2.591 (2)	175 (3)
O3—H3o···N2	0.84 (1)	1.88 (2)	2.632 (3)	149 (3)
N1—H1n···O1	0.87 (1)	1.90 (2)	2.614 (3)	139 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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