(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Zhao, Z.; Wang, Y.; Chen, Y.; Bi, L.

doi:10.1107/S1600536808038464

organic compounds

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Volume 64| Part 12| December 2008| Page o2408

doi:10.1107/S1600536808038464

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(E)-N′-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide

Zhen-dong Zhao,^a ^* Yu-min Wang,^a Yu-xiang Chen ^a and Liang-wu Bi ^a

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
^*Correspondence e-mail: minwangyu@126.com

(Received 3 November 2008; accepted 18 November 2008; online 22 November 2008)

The molecule of the title compound, C₁₇H₁₇BrN₂O₅, assumes an E configuration, with the 5-bromo-2-hydroxyphenyl and benzohydrazide units located on opposite sites of the C=N double bond. The dihedral angle between the planes of the two benzene rings is 32.48 (15)°. The crystal structure is stabilized by intramolecular O—H⋯N and intermolecular N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Yang et al. (1996 ); Nawar & Hosny (2000 ); Pelagatti et al. (1999 ); Ainscough et al. (1998 ). For related structures, see: Diao & Yu (2006 ); Jing et al. (2005 ); Wang et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₇BrN₂O₅
M_r = 409.24
Monoclinic, P 2₁ /c
a = 11.4157 (19) Å
b = 16.279 (3) Å
c = 9.3738 (16) Å
β = 100.210 (3)°
V = 1714.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.43 mm⁻¹
T = 273 (2) K [Unusual. Please check]
0.15 × 0.10 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.712, T_max = 0.868
8954 measured reflections
3037 independent reflections
2065 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.097
S = 1.01
3037 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.92	2.642 (3)	145
N1—H1A⋯O2ⁱ	0.86	2.14	2.888 (3)	146
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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: 10.1107/S1600536808038464/pv2120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038464/pv2120Isup2.hkl

checkCIF report

Comment top

Salicyladelhyde hydrazones have received considerable attention because of their possible applications in catalysis and pharmacology (Yang et al., 1996; Nawar & Hosny, 2000; Pelagatti et al., 1999; Ainscough et al., 1998). As part of our ongoing investigation on acylhydrazone compounds (Wang et al., 2008) and their metal complexes, we have obtained the title compound, (I), from a condensation of 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde, and report its crystal structure in this paper.

The molecular structure of (I) (Fig. 1) contains 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde moities that are located on opposite sides of the C═N double bond exhibiting an E configuration about C═N. The dihedral angle between the mean-planes of the two benzene rings is 32.48 (15)°. The crystal structure involves an intramolecular hydrogen bond O1–H1···N2, and is further stabilized by an intermolecular hydrogen bonds N1–H1A···O2, resulting in chains of molecules extended along the c-axis; details are given in Table 1 and Fig. 2. The bond distances and bond angles in (I) are in agreement with the corresponding dimensions reported for some structures closely related to (I) (Diao & Yu, 2006; Jing et al., 2005; Wang et al., 2008). (

Related literature top

For related literature, see: Yang et al. (1996); Nawar & Hosny (2000); Pelagatti et al. (1999); Ainscough et al. (1998). For related structures, see: Diao & Yu (2006); Jing et al. (2005); Wang et al. (2008).

Experimental top

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 5-bromo-2-hydroxybenzaldehyde (0.01 mol) was refluxed and stirred for 2h ; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. The packing of (I), showing the intermolecular hydrogen-bonded extended network.

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-3,4,5- trimethoxybenzohydrazide top

Crystal data top

C₁₇H₁₇BrN₂O₅	F(000) = 832
M_r = 409.24	D_x = 1.586 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2452 reflections
a = 11.4157 (19) Å	θ = 2.5–22.8°
b = 16.279 (3) Å	µ = 2.43 mm⁻¹
c = 9.3738 (16) Å	T = 273 K
β = 100.210 (3)°	Block, colourless
V = 1714.4 (5) Å³	0.15 × 0.10 × 0.06 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	3037 independent reflections
Radiation source: fine-focus sealed tube	2065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.712, T_max = 0.868	k = −19→19
8954 measured reflections	l = −11→8

Refinement top

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0439P)² + 0.6769P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.002
3037 reflections	Δρ_max = 0.43 e Å⁻³
228 parameters	Δρ_min = −0.54 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0171 (11)

Crystal data top

C₁₇H₁₇BrN₂O₅	V = 1714.4 (5) Å³
M_r = 409.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4157 (19) Å	µ = 2.43 mm⁻¹
b = 16.279 (3) Å	T = 273 K
c = 9.3738 (16) Å	0.15 × 0.10 × 0.06 mm
β = 100.210 (3)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3037 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2065 reflections with I > 2σ(I)
T_min = 0.712, T_max = 0.868	R_int = 0.033
8954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.01	Δρ_max = 0.43 e Å⁻³
3037 reflections	Δρ_min = −0.54 e Å⁻³
228 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	0.94048 (4)	1.21831 (2)	0.94475 (6)	0.0865 (2)
O1	0.9086 (2)	0.92631 (14)	1.3259 (2)	0.0609 (6)
H1	0.8677	0.8897	1.2824	0.091*
O2	0.74380 (19)	0.70776 (12)	1.2188 (2)	0.0493 (5)
O3	0.6562 (2)	0.42963 (12)	0.9513 (2)	0.0605 (6)
O4	0.4797 (2)	0.47058 (14)	0.7287 (2)	0.0661 (7)
O5	0.42036 (19)	0.62400 (14)	0.6698 (2)	0.0595 (6)
N1	0.7240 (2)	0.78966 (13)	1.0217 (2)	0.0413 (6)
H1A	0.6980	0.7944	0.9302	0.050*
N2	0.7787 (2)	0.85483 (14)	1.0984 (2)	0.0392 (6)
C1	0.9120 (3)	0.99080 (18)	1.2363 (3)	0.0446 (7)
C2	0.8549 (2)	0.98993 (16)	1.0913 (3)	0.0400 (7)
C3	0.8637 (3)	1.05886 (18)	1.0069 (3)	0.0485 (8)
H3	0.8252	1.0596	0.9107	0.058*
C4	0.9282 (3)	1.12578 (18)	1.0634 (4)	0.0542 (8)
C5	0.9863 (3)	1.1252 (2)	1.2051 (4)	0.0592 (9)
H5	1.0316	1.1702	1.2427	0.071*
C6	0.9772 (3)	1.0587 (2)	1.2899 (4)	0.0573 (9)
H6	1.0158	1.0591	1.3861	0.069*
C7	0.7914 (2)	0.91924 (17)	1.0253 (3)	0.0417 (7)
H7	0.7588	0.9206	0.9271	0.050*
C8	0.7105 (2)	0.71797 (17)	1.0892 (3)	0.0369 (6)
C9	0.6508 (2)	0.65335 (17)	0.9912 (3)	0.0381 (7)
C10	0.6826 (3)	0.57283 (17)	1.0217 (3)	0.0416 (7)
H10	0.7397	0.5600	1.1023	0.050*
C11	0.6292 (3)	0.51139 (17)	0.9317 (3)	0.0450 (7)
C12	0.5412 (3)	0.52992 (18)	0.8141 (3)	0.0460 (7)
C13	0.5089 (3)	0.61112 (19)	0.7852 (3)	0.0445 (7)
C14	0.5643 (2)	0.67246 (18)	0.8733 (3)	0.0413 (7)
H14	0.5434	0.7270	0.8534	0.050*
C15	0.7519 (3)	0.4079 (2)	1.0611 (4)	0.0713 (10)
H15A	0.8233	0.4340	1.0431	0.107*
H15B	0.7622	0.3493	1.0618	0.107*
H15C	0.7355	0.4255	1.1533	0.107*
C16	0.5452 (4)	0.4238 (2)	0.6446 (4)	0.0853 (12)
H16A	0.5791	0.4595	0.5812	0.128*
H16B	0.4935	0.3848	0.5880	0.128*
H16C	0.6077	0.3952	0.7071	0.128*
C17	0.3907 (3)	0.7059 (2)	0.6315 (4)	0.0697 (10)
H17A	0.3538	0.7308	0.7052	0.105*
H17B	0.3364	0.7070	0.5407	0.105*
H17C	0.4616	0.7357	0.6225	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0686 (3)	0.0506 (3)	0.1438 (5)	0.00267 (18)	0.0284 (3)	0.0265 (2)
O1	0.0746 (17)	0.0646 (15)	0.0377 (12)	−0.0140 (12)	−0.0059 (11)	−0.0017 (11)
O2	0.0660 (14)	0.0498 (12)	0.0287 (11)	0.0048 (10)	−0.0008 (10)	−0.0018 (9)
O3	0.0799 (16)	0.0411 (12)	0.0584 (14)	−0.0084 (11)	0.0066 (13)	−0.0024 (11)
O4	0.0701 (16)	0.0687 (15)	0.0606 (15)	−0.0312 (12)	0.0147 (13)	−0.0247 (12)
O5	0.0551 (14)	0.0737 (16)	0.0426 (13)	−0.0110 (12)	−0.0106 (11)	−0.0072 (11)
N1	0.0504 (14)	0.0429 (14)	0.0266 (12)	−0.0088 (11)	−0.0039 (11)	−0.0032 (11)
N2	0.0450 (14)	0.0359 (13)	0.0336 (13)	−0.0029 (11)	−0.0019 (11)	−0.0071 (11)
C1	0.0470 (17)	0.0485 (18)	0.0377 (17)	−0.0016 (14)	0.0053 (15)	−0.0063 (14)
C2	0.0383 (16)	0.0407 (16)	0.0394 (17)	0.0028 (13)	0.0032 (14)	−0.0047 (13)
C3	0.0459 (18)	0.0463 (18)	0.0512 (19)	0.0034 (14)	0.0031 (15)	0.0013 (15)
C4	0.0466 (19)	0.0399 (17)	0.079 (3)	0.0017 (14)	0.0184 (19)	0.0001 (17)
C5	0.051 (2)	0.0457 (19)	0.082 (3)	−0.0077 (15)	0.0138 (19)	−0.0220 (19)
C6	0.052 (2)	0.063 (2)	0.054 (2)	−0.0096 (16)	0.0002 (16)	−0.0239 (18)
C7	0.0454 (17)	0.0456 (17)	0.0304 (15)	−0.0010 (14)	−0.0032 (13)	−0.0056 (14)
C8	0.0372 (15)	0.0422 (16)	0.0308 (16)	0.0025 (13)	0.0051 (13)	−0.0042 (13)
C9	0.0416 (16)	0.0406 (16)	0.0325 (15)	−0.0050 (13)	0.0077 (13)	−0.0048 (13)
C10	0.0436 (17)	0.0463 (17)	0.0339 (16)	−0.0040 (14)	0.0043 (13)	−0.0037 (13)
C11	0.0531 (19)	0.0387 (16)	0.0471 (18)	−0.0075 (14)	0.0194 (16)	−0.0045 (14)
C12	0.0483 (18)	0.0507 (18)	0.0400 (18)	−0.0182 (15)	0.0107 (15)	−0.0130 (15)
C13	0.0396 (17)	0.060 (2)	0.0333 (17)	−0.0103 (14)	0.0033 (14)	−0.0069 (14)
C14	0.0429 (17)	0.0436 (17)	0.0371 (16)	−0.0028 (13)	0.0064 (14)	−0.0015 (13)
C15	0.084 (3)	0.0450 (19)	0.083 (3)	0.0038 (18)	0.010 (2)	0.0028 (18)
C16	0.113 (3)	0.066 (2)	0.075 (3)	−0.008 (2)	0.011 (3)	−0.035 (2)
C17	0.056 (2)	0.084 (3)	0.061 (2)	−0.0003 (19)	−0.0123 (18)	0.004 (2)

Geometric parameters (Å, º) top

Br1—C4	1.892 (3)	C5—H5	0.9300
O1—C1	1.350 (4)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.219 (3)	C8—C9	1.481 (4)
O3—C11	1.371 (3)	C9—C10	1.377 (4)
O3—C15	1.407 (4)	C9—C14	1.381 (4)
O4—C12	1.366 (3)	C10—C11	1.379 (4)
O4—C16	1.403 (4)	C10—H10	0.9300
O5—C13	1.359 (3)	C11—C12	1.386 (4)
O5—C17	1.406 (4)	C12—C13	1.386 (4)
N1—C8	1.349 (3)	C13—C14	1.376 (4)
N1—N2	1.369 (3)	C14—H14	0.9300
N1—H1A	0.8600	C15—H15A	0.9600
N2—C7	1.274 (3)	C15—H15B	0.9600
C1—C6	1.378 (4)	C15—H15C	0.9600
C1—C2	1.399 (4)	C16—H16A	0.9600
C2—C3	1.387 (4)	C16—H16B	0.9600
C2—C7	1.440 (4)	C16—H16C	0.9600
C3—C4	1.368 (4)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.375 (5)	C17—H17C	0.9600
C5—C6	1.357 (5)

C1—O1—H1	109.5	C14—C9—C8	121.4 (3)
C11—O3—C15	118.0 (2)	C9—C10—C11	119.4 (3)
C12—O4—C16	116.3 (3)	C9—C10—H10	120.3
C13—O5—C17	117.4 (2)	C11—C10—H10	120.3
C8—N1—N2	120.2 (2)	O3—C11—C10	123.9 (3)
C8—N1—H1A	119.9	O3—C11—C12	115.6 (3)
N2—N1—H1A	119.9	C10—C11—C12	120.5 (3)
C7—N2—N1	116.1 (2)	O4—C12—C13	117.9 (3)
O1—C1—C6	118.1 (3)	O4—C12—C11	122.4 (3)
O1—C1—C2	122.5 (3)	C13—C12—C11	119.5 (3)
C6—C1—C2	119.4 (3)	O5—C13—C14	124.3 (3)
C3—C2—C1	118.5 (3)	O5—C13—C12	115.9 (3)
C3—C2—C7	118.9 (3)	C14—C13—C12	119.8 (3)
C1—C2—C7	122.5 (3)	C13—C14—C9	120.3 (3)
C4—C3—C2	120.8 (3)	C13—C14—H14	119.9
C4—C3—H3	119.6	C9—C14—H14	119.9
C2—C3—H3	119.6	O3—C15—H15A	109.5
C3—C4—C5	120.2 (3)	O3—C15—H15B	109.5
C3—C4—Br1	119.8 (3)	H15A—C15—H15B	109.5
C5—C4—Br1	120.0 (3)	O3—C15—H15C	109.5
C6—C5—C4	119.9 (3)	H15A—C15—H15C	109.5
C6—C5—H5	120.1	H15B—C15—H15C	109.5
C4—C5—H5	120.1	O4—C16—H16A	109.5
C5—C6—C1	121.2 (3)	O4—C16—H16B	109.5
C5—C6—H6	119.4	H16A—C16—H16B	109.5
C1—C6—H6	119.4	O4—C16—H16C	109.5
N2—C7—C2	121.6 (3)	H16A—C16—H16C	109.5
N2—C7—H7	119.2	H16B—C16—H16C	109.5
C2—C7—H7	119.2	O5—C17—H17A	109.5
O2—C8—N1	123.0 (2)	O5—C17—H17B	109.5
O2—C8—C9	123.3 (3)	H17A—C17—H17B	109.5
N1—C8—C9	113.7 (2)	O5—C17—H17C	109.5
C10—C9—C14	120.4 (3)	H17A—C17—H17C	109.5
C10—C9—C8	118.2 (3)	H17B—C17—H17C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.92	2.642 (3)	145
N1—H1A···O2ⁱ	0.86	2.14	2.888 (3)	146

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇BrN₂O₅
M_r	409.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	11.4157 (19), 16.279 (3), 9.3738 (16)
β (°)	100.210 (3)
V (Å³)	1714.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.43
Crystal size (mm)	0.15 × 0.10 × 0.06

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.712, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	8954, 3037, 2065
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.097, 1.01
No. of reflections	3037
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.54

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
O1—H1···N2	0.82	1.92	2.642 (3)	145
N1—H1A···O2ⁱ	0.86	2.14	2.888 (3)	146

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of China (grant No. 30571466).

References

Ainscough, E. W., Brodie, A. M., Dobbs, A. J., Ranford, J. D. & Waters, J. M. (1998). Inorg Chim. Acta, 267, 27–38. CSD CrossRef CAS Web of Science Google Scholar
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