(E)-N′-[1-(4-Bromo­phen­yl)ethyl­idene]-2-hydroxy­benzohydrazide

Fan, C.-G.; Song, M.-Z.

doi:10.1107/S1600536809042081

organic compounds

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Volume 65| Part 11| November 2009| Page o2792

https://doi.org/10.1107/S1600536809042081

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(E)-N′-[1-(4-Bromophenyl)ethylidene]-2-hydroxybenzohydrazide

Chuan-Gang Fan ^a ^* and Ming-Zhi Song ^a

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 26 September 2009; accepted 13 October 2009; online 17 October 2009)

In the title compound, C₁₅H₁₃BrN₂O₂, the two aromatic rings form a dihedral angle of 7.9 (1)° and an intramolecular N—H⋯O hydrogen bond influences the molecular conformation. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into chains propagated in [001]. The crystal packing exhibits also π–π interactions, which pair molecules into centrosymmetric dimers with short intermolecular distances of 3.671 (4) Å between the centroids of aromatic rings.

Related literature

For the biological properties of Schiff base ligands, see: Jeewoth et al. (1999 ). For related structures, see: Fun et al. (2008 ); Cui et al. (2009 ); Nie (2008 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₂
M_r = 333.18
Monoclinic, C 2/c
a = 27.805 (3) Å
b = 7.9061 (9) Å
c = 13.5002 (15) Å
β = 113.344 (2)°
V = 2724.8 (5) Å³
Z = 8
Mo Kα radiation
μ = 3.02 mm⁻¹
T = 298 K
0.39 × 0.14 × 0.12 mm

Data collection

Siemens SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.386, T_max = 0.713
6480 measured reflections
2397 independent reflections
1602 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.111
S = 0.95
2397 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.95	2.637 (3)	136
O2—H2⋯O1ⁱ	0.82	1.86	2.677 (3)	178
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042081/cv2623sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042081/cv2623Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have received considerable attention during the last decades due to their structures and biological properties (Jeewoth et al., 1999). We report here the crystal structure of the title Schiff base compound (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie, 2008; Fun et al., 2008; Cui et al., 2009). The C9=N2 bond length in the molecule is 1.282 (4) °, showing the double-bond character. The dihedral angle between the benzene ring C2-C7 and the benzene ring C10-C15 is 7.9 (1)°, indicating that two these rings are approximately coplanar.

In the crystal, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [001]. The crystal packing exhibits also π···π interactions, which pair molecules into centrosymmetric dimers with short intermolecular distance of 3.671 (4) Å between the centroids of aromatic rings.

Related literature top

For the biological properties of Schiff base ligands, see: Jeewoth et al. (1999). For related crystal structures, see: Fun et al. (2008); Cui et al. (2009); Nie (2008).

Experimental top

Salicyloyl hydrazide (5.0 mmol), 20 ml e thanol and 4-bromoacetophenone (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystallized from ethanol. Elemental analysis: calculated for C₁₅H₁₃BrN₂O₂: C 54.07, H 3.93, N 8.41%; found: C 54.21, H 3.85, N 8.52%.

Structure description top

For the biological properties of Schiff base ligands, see: Jeewoth et al. (1999). For related crystal structures, see: Fun et al. (2008); Cui et al. (2009); Nie (2008).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008)'.

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

(E)-N'-[1-(4-Bromophenyl)ethylidene]-2-hydroxybenzohydrazide top

Crystal data top

C₁₅H₁₃BrN₂O₂	F(000) = 1344
M_r = 333.18	D_x = 1.624 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.805 (3) Å	Cell parameters from 1955 reflections
b = 7.9061 (9) Å	θ = 2.7–26.0°
c = 13.5002 (15) Å	µ = 3.02 mm⁻¹
β = 113.344 (2)°	T = 298 K
V = 2724.8 (5) Å³	Block, colourless
Z = 8	0.39 × 0.14 × 0.12 mm

Data collection top

Siemens SMART APEX CCD area-detector diffractometer	2397 independent reflections
Radiation source: fine-focus sealed tube	1602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
phi and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→32
T_min = 0.386, T_max = 0.713	k = −5→9
6480 measured reflections	l = −16→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0507P)²] where P = (F_o² + 2F_c²)/3
2397 reflections	(Δ/σ)_max = 0.002
181 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.74 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₂	V = 2724.8 (5) Å³
M_r = 333.18	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 27.805 (3) Å	µ = 3.02 mm⁻¹
b = 7.9061 (9) Å	T = 298 K
c = 13.5002 (15) Å	0.39 × 0.14 × 0.12 mm
β = 113.344 (2)°

Data collection top

Siemens SMART APEX CCD area-detector diffractometer	2397 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1602 reflections with I > 2σ(I)
T_min = 0.386, T_max = 0.713	R_int = 0.071
6480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 0.95	Δρ_max = 0.54 e Å⁻³
2397 reflections	Δρ_min = −0.74 e Å⁻³
181 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.

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.

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

	x	y	z	U_iso*/U_eq
Br1	1.171700 (16)	1.05278 (6)	1.41157 (3)	0.0585 (2)
N1	0.92749 (11)	0.6137 (4)	0.9225 (2)	0.0342 (8)
H1	0.9291	0.6170	0.8602	0.041*
N2	0.96688 (11)	0.6843 (4)	1.0103 (2)	0.0325 (7)
O1	0.88354 (11)	0.5298 (4)	1.02232 (19)	0.0555 (9)
O2	0.88245 (10)	0.5567 (4)	0.71317 (18)	0.0434 (7)
H2	0.8821	0.5286	0.6545	0.065*
C1	0.88626 (13)	0.5393 (5)	0.9337 (3)	0.0329 (9)
C2	0.84455 (14)	0.4681 (5)	0.8353 (3)	0.0317 (9)
C3	0.84277 (13)	0.4765 (5)	0.7298 (3)	0.0325 (9)
C4	0.80124 (15)	0.4043 (6)	0.6450 (3)	0.0450 (11)
H4	0.7998	0.4127	0.5752	0.054*
C5	0.76224 (15)	0.3206 (6)	0.6629 (3)	0.0467 (11)
H5	0.7347	0.2722	0.6053	0.056*
C6	0.76374 (15)	0.3079 (5)	0.7662 (3)	0.0461 (11)
H6	0.7376	0.2496	0.7787	0.055*
C7	0.80399 (14)	0.3818 (5)	0.8496 (3)	0.0394 (10)
H7	0.8044	0.3744	0.9187	0.047*
C8	1.01117 (15)	0.7562 (6)	0.8889 (3)	0.0453 (11)
H8A	1.0056	0.6454	0.8573	0.068*
H8B	1.0457	0.7943	0.9003	0.068*
H8C	0.9858	0.8331	0.8413	0.068*
C9	1.00561 (13)	0.7498 (5)	0.9952 (2)	0.0314 (9)
C10	1.04721 (13)	0.8237 (5)	1.0939 (3)	0.0312 (9)
C11	1.04697 (14)	0.7866 (5)	1.1949 (3)	0.0387 (10)
H11	1.0216	0.7137	1.1993	0.046*
C12	1.08322 (15)	0.8551 (6)	1.2876 (3)	0.0441 (10)
H12	1.0822	0.8297	1.3540	0.053*
C13	1.12116 (14)	0.9617 (5)	1.2819 (3)	0.0376 (9)
C14	1.12300 (16)	0.9996 (6)	1.1834 (3)	0.0446 (10)
H14	1.1487	1.0713	1.1795	0.054*
C15	1.08594 (14)	0.9290 (5)	1.0911 (3)	0.0393 (10)
H15	1.0873	0.9537	1.0248	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0516 (3)	0.0628 (4)	0.0480 (3)	−0.0060 (3)	0.0059 (2)	−0.0110 (2)
N1	0.0355 (17)	0.045 (2)	0.0228 (15)	0.0001 (16)	0.0125 (13)	−0.0005 (14)
N2	0.0320 (17)	0.039 (2)	0.0259 (16)	0.0008 (15)	0.0105 (14)	−0.0028 (14)
O1	0.0562 (18)	0.088 (3)	0.0281 (14)	−0.0174 (17)	0.0231 (13)	−0.0038 (15)
O2	0.0502 (16)	0.060 (2)	0.0236 (12)	−0.0083 (15)	0.0181 (12)	−0.0062 (12)
C1	0.036 (2)	0.038 (2)	0.0268 (19)	0.0080 (19)	0.0146 (16)	0.0022 (17)
C2	0.0311 (19)	0.032 (2)	0.0301 (19)	0.0081 (18)	0.0104 (16)	0.0016 (17)
C3	0.034 (2)	0.035 (2)	0.0305 (19)	0.0059 (18)	0.0151 (17)	0.0000 (17)
C4	0.050 (3)	0.054 (3)	0.027 (2)	0.003 (2)	0.0108 (19)	−0.0065 (19)
C5	0.034 (2)	0.048 (3)	0.048 (2)	−0.001 (2)	0.0052 (19)	−0.009 (2)
C6	0.038 (2)	0.049 (3)	0.053 (3)	−0.002 (2)	0.020 (2)	−0.002 (2)
C7	0.037 (2)	0.044 (3)	0.036 (2)	0.001 (2)	0.0145 (18)	0.0041 (19)
C8	0.048 (2)	0.054 (3)	0.039 (2)	−0.003 (2)	0.0221 (19)	−0.005 (2)
C9	0.037 (2)	0.032 (2)	0.0277 (19)	0.0079 (18)	0.0145 (17)	0.0014 (16)
C10	0.031 (2)	0.031 (2)	0.0338 (19)	0.0078 (18)	0.0158 (16)	0.0012 (17)
C11	0.040 (2)	0.044 (3)	0.035 (2)	−0.005 (2)	0.0175 (18)	−0.0008 (19)
C12	0.051 (2)	0.052 (3)	0.030 (2)	0.004 (2)	0.0164 (19)	0.0058 (19)
C13	0.032 (2)	0.036 (2)	0.041 (2)	0.0022 (19)	0.0106 (17)	−0.0046 (18)
C14	0.042 (2)	0.043 (3)	0.049 (2)	−0.005 (2)	0.018 (2)	−0.001 (2)
C15	0.043 (2)	0.044 (3)	0.036 (2)	0.000 (2)	0.0210 (18)	0.0068 (19)

Geometric parameters (Å, º) top

Br1—C13	1.899 (4)	C6—H6	0.9300
N1—C1	1.349 (5)	C7—H7	0.9300
N1—N2	1.374 (4)	C8—C9	1.504 (4)
N1—H1	0.8600	C8—H8A	0.9600
N2—C9	1.282 (4)	C8—H8B	0.9600
O1—C1	1.231 (4)	C8—H8C	0.9600
O2—C3	1.366 (4)	C9—C10	1.494 (5)
O2—H2	0.8200	C10—C15	1.374 (5)
C1—C2	1.485 (5)	C10—C11	1.398 (5)
C2—C7	1.395 (5)	C11—C12	1.369 (5)
C2—C3	1.407 (5)	C11—H11	0.9300
C3—C4	1.386 (5)	C12—C13	1.376 (5)
C4—C5	1.371 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.384 (5)
C5—C6	1.383 (5)	C14—C15	1.382 (5)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.365 (5)	C15—H15	0.9300

C1—N1—N2	120.2 (3)	C9—C8—H8B	109.5
C1—N1—H1	119.9	H8A—C8—H8B	109.5
N2—N1—H1	119.9	C9—C8—H8C	109.5
C9—N2—N1	117.3 (3)	H8A—C8—H8C	109.5
C3—O2—H2	109.5	H8B—C8—H8C	109.5
O1—C1—N1	121.2 (3)	N2—C9—C10	114.8 (3)
O1—C1—C2	121.3 (3)	N2—C9—C8	125.2 (3)
N1—C1—C2	117.6 (3)	C10—C9—C8	120.1 (3)
C7—C2—C3	117.2 (3)	C15—C10—C11	117.5 (3)
C7—C2—C1	116.7 (3)	C15—C10—C9	123.4 (3)
C3—C2—C1	126.1 (3)	C11—C10—C9	119.1 (3)
O2—C3—C4	121.2 (3)	C12—C11—C10	121.5 (4)
O2—C3—C2	118.8 (3)	C12—C11—H11	119.3
C4—C3—C2	120.0 (3)	C10—C11—H11	119.3
C5—C4—C3	120.8 (3)	C11—C12—C13	119.7 (3)
C5—C4—H4	119.6	C11—C12—H12	120.2
C3—C4—H4	119.6	C13—C12—H12	120.2
C4—C5—C6	120.2 (4)	C12—C13—C14	120.5 (3)
C4—C5—H5	119.9	C12—C13—Br1	119.0 (3)
C6—C5—H5	119.9	C14—C13—Br1	120.5 (3)
C7—C6—C5	119.2 (4)	C15—C14—C13	118.8 (4)
C7—C6—H6	120.4	C15—C14—H14	120.6
C5—C6—H6	120.4	C13—C14—H14	120.6
C6—C7—C2	122.6 (3)	C10—C15—C14	122.2 (3)
C6—C7—H7	118.7	C10—C15—H15	118.9
C2—C7—H7	118.7	C14—C15—H15	118.9
C9—C8—H8A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.95	2.637 (3)	136
O2—H2···O1ⁱ	0.82	1.86	2.677 (3)	178

Symmetry code: (i) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₂
M_r	333.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	27.805 (3), 7.9061 (9), 13.5002 (15)
β (°)	113.344 (2)
V (Å³)	2724.8 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.02
Crystal size (mm)	0.39 × 0.14 × 0.12

Data collection
Diffractometer	Siemens SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.386, 0.713
No. of measured, independent and observed [I > 2σ(I)] reflections	6480, 2397, 1602
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.111, 0.95
No. of reflections	2397
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.74

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008)'.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.95	2.637 (3)	135.7
O2—H2···O1ⁱ	0.82	1.86	2.677 (3)	177.9

Symmetry code: (i) x, −y+1, z−1/2.

Acknowledgements

The authors acknowledge the financial support of the Foundation of Binzhou University (grant No. BZXYLG200609).

References

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