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

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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.097
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        273 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        273 K

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   0 ALERT level B = Potentially serious problem
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   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

All H atoms were placed geometrically at the distances: C—H(methyl) = 0.96, C—H(aryl) = 0.93, N—H = 0.86 and O—H = 0.82 Å and included in the refinement in riding motion approximation with U_iso(H) = 1.2 or 1.5U_eq of the carrier atom.

Computing details

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

	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

Crystal data

C17H17BrN2O5	F(000) = 832
Mr = 409.24	Dx = 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) Å^3	0.15 × 0.10 × 0.06 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 0.6769P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
3037 reflections	Δρmax = 0.43 e Å^−3
228 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0171 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.86	2.14	2.888 (3)	146

Symmetry code: (i) x, −y+3/2, z−1/2.