(E)-N′-(5-Bromo-2-hy­droxy­benzyl­idene)-4-hy­droxy-3-meth­oxy­benzohydrazide methanol solvate

Liu, S.-Y.; You, Z.

doi:10.1107/S1600536810022063

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1662

doi:10.1107/S1600536810022063

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(E)-N′-(5-Bromo-2-hydroxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide methanol solvate

Shi-Yong Liu ^a ^* and Zhonglu You ^b

^aCollege of Chemistry & Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China, and ^bDepartment of Chemistry, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: liushiyong2010@yahoo.cn

(Received 7 June 2010; accepted 9 June 2010; online 16 June 2010)

In the title compound, C₁₅H₁₃BrN₂O₄·CH₄O, the two benzene rings form a dihedral angle of 3.2 (2)°. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, molecules are linked through O—H⋯O and N—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (10 $[\overline{1}]$ ).

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ); Zhu et al. (2009 ); Jimenez-Pulido et al. (2008 ); Raj et al. (2007 ); Zhong et al. (2007 ). For crystal structures of hydrazone compounds, see: Khaledi et al. (2009 ); Warad et al. (2009 ); Back et al. (2009 ); Vijayakumar et al. (2009 ). For related structures, see: Cao (2009 ); Xu et al. (2009 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₃BrN₂O₄·CH₄O
M_r = 397.23
Monoclinic, P 2₁ /n
a = 7.4412 (4) Å
b = 17.5287 (9) Å
c = 12.5555 (8) Å
β = 91.200 (3)°
V = 1637.31 (16) Å³
Z = 4
Mo Kα radiation
μ = 2.54 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.547, T_max = 0.593
9411 measured reflections
3368 independent reflections
2230 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.082
S = 1.01
3368 reflections
225 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5	0.89 (1)	2.07 (1)	2.949 (3)	167 (3)
O1—H1⋯N1	0.82	1.98	2.686 (3)	145
O4—H4⋯O2ⁱ	0.82	1.87	2.671 (3)	166
O5—H5⋯O3ⁱⁱ	0.82	2.46	3.125 (3)	139
O5—H5⋯O4ⁱⁱ	0.82	2.57	3.252 (3)	141
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022063/ci5098sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022063/ci5098Isup2.hkl

checkCIF report

Comment top

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Zhu et al., 2009; Jimenez-Pulido et al., 2008; Raj et al., 2007; Zhong et al., 2007). The study on the crystal structures of such compounds is of particular interest (Khaledi et al., 2009; Warad et al., 2009; Back et al., 2009; Vijayakumar et al., 2009). We report herein the crystal structure of the title new hydrazone.

The asymmetric unit of the title compound contains a benzohydrazide molecule and a methanol solvate molecule, as shown in Fig. 1. The dihedral angle between the two benzene rings is 3.2 (2)°, indicating they are nearly coplanar. Atom C15 deviates from the C9–C14 benzene ring by 0.188 (2) Å. All the bond lengths are comparable to those observed in related structures (Cao, 2009; Xu et al., 2009; Shafiq et al., 2009).

In the crystal structure, the hydrazone and methanol molecules are linked through O—H···N, O—H···O, and N—H···O hydrogen bonds, to form a two-dimensional network parallel to the (101) (Fig. 2 and Table 1).

Related literature top

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010); Zhu et al. (2009); Jimenez-Pulido et al. (2008); Raj et al. (2007); Zhong et al. (2007). For crystal structures of hydrazone compounds, see: Khaledi et al. (2009); Warad et al. (2009); Back et al. (2009); Vijayakumar et al. (2009). For related structures, see: Cao (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 5-bromosalicylaldehyde (0.05 mol, 10 g) and 4-hydroxy-3-methoxybenzohydrazide (0.05 mol, 9 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the methanol solution for a period of 5 d.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 the title compound. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(5-Bromo-2-hydroxybenzylidene)-4-hydroxy-3- methoxybenzohydrazide methanol solvate top

Crystal data top

C₁₅H₁₃BrN₂O₄·CH₄O	F(000) = 808
M_r = 397.23	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2105 reflections
a = 7.4412 (4) Å	θ = 2.3–24.0°
b = 17.5287 (9) Å	µ = 2.54 mm⁻¹
c = 12.5555 (8) Å	T = 298 K
β = 91.200 (3)°	Block, colourless
V = 1637.31 (16) Å³	0.27 × 0.23 × 0.23 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3368 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 26.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.547, T_max = 0.593	k = −19→21
9411 measured reflections	l = −13→15

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
3368 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.24 e Å⁻³
1 restraint	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₄·CH₄O	V = 1637.31 (16) Å³
M_r = 397.23	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4412 (4) Å	µ = 2.54 mm⁻¹
b = 17.5287 (9) Å	T = 298 K
c = 12.5555 (8) Å	0.27 × 0.23 × 0.23 mm
β = 91.200 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3368 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2230 reflections with I > 2σ(I)
T_min = 0.547, T_max = 0.593	R_int = 0.039
9411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.24 e Å⁻³
3368 reflections	Δρ_min = −0.31 e Å⁻³
225 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.18595 (5)	0.149648 (15)	0.52921 (3)	0.05687 (14)
N1	0.2299 (3)	0.51490 (11)	0.46909 (16)	0.0362 (5)
N2	0.2800 (3)	0.57506 (11)	0.53449 (16)	0.0370 (5)
O1	0.0923 (3)	0.44648 (10)	0.29416 (14)	0.0550 (6)
H1	0.1171	0.4831	0.3324	0.083*
O2	0.2525 (3)	0.65966 (10)	0.40042 (15)	0.0508 (5)
O3	0.3700 (3)	0.91862 (9)	0.56842 (13)	0.0438 (5)
O4	0.5122 (3)	0.89035 (10)	0.75563 (14)	0.0513 (5)
H4	0.5720	0.8758	0.8073	0.077*
O5	0.3071 (3)	0.51702 (11)	0.75469 (16)	0.0561 (6)
H5	0.2163	0.4979	0.7793	0.084*
C1	0.1853 (4)	0.38040 (14)	0.4545 (2)	0.0363 (6)
C2	0.1173 (4)	0.38095 (15)	0.3500 (2)	0.0382 (6)
C3	0.0704 (4)	0.31294 (16)	0.3002 (2)	0.0468 (7)
H3	0.0236	0.3136	0.2309	0.056*
C4	0.0928 (4)	0.24469 (15)	0.3524 (2)	0.0489 (8)
H4A	0.0631	0.1992	0.3182	0.059*
C5	0.1593 (4)	0.24389 (14)	0.4555 (2)	0.0408 (7)
C6	0.2052 (4)	0.31014 (14)	0.5065 (2)	0.0393 (7)
H6	0.2498	0.3086	0.5763	0.047*
C7	0.2359 (4)	0.44864 (14)	0.5118 (2)	0.0386 (7)
H7	0.2743	0.4443	0.5824	0.046*
C8	0.2886 (3)	0.64661 (13)	0.4938 (2)	0.0329 (6)
C9	0.3473 (3)	0.70777 (13)	0.56902 (19)	0.0305 (6)
C10	0.3292 (3)	0.78280 (13)	0.5325 (2)	0.0328 (6)
H10	0.2810	0.7921	0.4648	0.039*
C11	0.3827 (3)	0.84311 (12)	0.5964 (2)	0.0317 (6)
C12	0.4587 (4)	0.82893 (14)	0.69653 (19)	0.0336 (6)
C13	0.4745 (4)	0.75503 (13)	0.7325 (2)	0.0357 (6)
H13	0.5227	0.7457	0.8002	0.043*
C14	0.4193 (3)	0.69455 (14)	0.66906 (19)	0.0350 (6)
H14	0.4310	0.6448	0.6941	0.042*
C15	0.3218 (4)	0.93558 (16)	0.4607 (2)	0.0530 (8)
H15A	0.4045	0.9110	0.4141	0.079*
H15B	0.3261	0.9898	0.4498	0.079*
H15C	0.2022	0.9174	0.4455	0.079*
C16	0.4575 (5)	0.4742 (2)	0.7866 (3)	0.0815 (11)
H16A	0.5649	0.5019	0.7707	0.122*
H16B	0.4572	0.4264	0.7491	0.122*
H16C	0.4536	0.4648	0.8618	0.122*
H2	0.291 (4)	0.5653 (18)	0.6041 (10)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0671 (2)	0.02604 (16)	0.0779 (3)	−0.00003 (14)	0.01145 (17)	0.00364 (15)
N1	0.0442 (14)	0.0265 (12)	0.0378 (13)	−0.0026 (10)	−0.0020 (10)	−0.0059 (10)
N2	0.0540 (15)	0.0219 (11)	0.0346 (12)	−0.0025 (10)	−0.0071 (12)	−0.0032 (10)
O1	0.0824 (16)	0.0330 (11)	0.0492 (12)	−0.0019 (11)	−0.0106 (11)	0.0004 (9)
O2	0.0814 (16)	0.0344 (11)	0.0359 (11)	−0.0045 (10)	−0.0189 (10)	0.0029 (8)
O3	0.0658 (14)	0.0215 (9)	0.0437 (11)	0.0019 (8)	−0.0123 (10)	0.0040 (8)
O4	0.0815 (17)	0.0257 (10)	0.0458 (13)	0.0000 (9)	−0.0218 (11)	−0.0052 (8)
O5	0.0667 (15)	0.0455 (12)	0.0558 (13)	−0.0083 (11)	−0.0048 (12)	0.0131 (10)
C1	0.0394 (17)	0.0283 (13)	0.0413 (16)	−0.0033 (12)	0.0036 (13)	−0.0056 (12)
C2	0.0431 (17)	0.0291 (13)	0.0424 (16)	−0.0010 (12)	0.0031 (13)	−0.0013 (12)
C3	0.052 (2)	0.0403 (17)	0.0474 (17)	−0.0067 (14)	−0.0019 (14)	−0.0107 (14)
C4	0.057 (2)	0.0309 (15)	0.059 (2)	−0.0117 (13)	0.0078 (16)	−0.0125 (14)
C5	0.0424 (17)	0.0249 (14)	0.0554 (19)	−0.0001 (11)	0.0095 (14)	−0.0025 (13)
C6	0.0464 (18)	0.0289 (14)	0.0428 (16)	−0.0031 (12)	0.0026 (14)	−0.0021 (12)
C7	0.0520 (18)	0.0277 (14)	0.0358 (15)	−0.0001 (12)	−0.0031 (13)	−0.0012 (12)
C8	0.0380 (16)	0.0268 (13)	0.0338 (15)	−0.0014 (11)	−0.0027 (12)	0.0006 (11)
C9	0.0362 (16)	0.0212 (12)	0.0341 (14)	−0.0007 (10)	0.0015 (12)	0.0009 (10)
C10	0.0365 (16)	0.0285 (13)	0.0331 (14)	0.0023 (11)	−0.0051 (12)	0.0039 (11)
C11	0.0375 (16)	0.0179 (12)	0.0396 (15)	0.0030 (10)	−0.0003 (12)	0.0015 (11)
C12	0.0395 (16)	0.0267 (13)	0.0343 (15)	−0.0007 (11)	−0.0030 (12)	−0.0031 (11)
C13	0.0483 (18)	0.0307 (14)	0.0277 (13)	−0.0004 (12)	−0.0081 (12)	0.0018 (11)
C14	0.0455 (17)	0.0242 (13)	0.0352 (15)	−0.0015 (11)	−0.0032 (13)	0.0059 (11)
C15	0.077 (2)	0.0306 (15)	0.0507 (19)	−0.0022 (15)	−0.0197 (16)	0.0146 (13)
C16	0.080 (3)	0.077 (3)	0.087 (3)	0.003 (2)	−0.015 (2)	0.018 (2)

Geometric parameters (Å, º) top

Br1—C5	1.902 (3)	C4—H4A	0.93
N1—C7	1.279 (3)	C5—C6	1.367 (3)
N1—N2	1.383 (3)	C6—H6	0.93
N2—C8	1.356 (3)	C7—H7	0.93
N2—H2	0.893 (10)	C8—C9	1.489 (3)
O1—C2	1.357 (3)	C9—C14	1.375 (3)
O1—H1	0.82	C9—C10	1.399 (3)
O2—C8	1.218 (3)	C10—C11	1.381 (3)
O3—C11	1.372 (3)	C10—H10	0.93
O3—C15	1.423 (3)	C11—C12	1.390 (3)
O4—C12	1.362 (3)	C12—C13	1.376 (3)
O4—H4	0.82	C13—C14	1.383 (3)
O5—C16	1.400 (4)	C13—H13	0.93
O5—H5	0.82	C14—H14	0.93
C1—C2	1.395 (4)	C15—H15A	0.96
C1—C6	1.401 (4)	C15—H15B	0.96
C1—C7	1.442 (3)	C15—H15C	0.96
C2—C3	1.388 (4)	C16—H16A	0.96
C3—C4	1.373 (4)	C16—H16B	0.96
C3—H3	0.93	C16—H16C	0.96
C4—C5	1.376 (4)

C7—N1—N2	115.9 (2)	N2—C8—C9	116.2 (2)
C8—N2—N1	119.7 (2)	C14—C9—C10	119.4 (2)
C8—N2—H2	123 (2)	C14—C9—C8	124.2 (2)
N1—N2—H2	117 (2)	C10—C9—C8	116.4 (2)
C2—O1—H1	109.5	C11—C10—C9	120.3 (2)
C11—O3—C15	117.37 (19)	C11—C10—H10	119.9
C12—O4—H4	109.5	C9—C10—H10	119.9
C16—O5—H5	109.5	O3—C11—C10	124.9 (2)
C2—C1—C6	118.5 (2)	O3—C11—C12	115.4 (2)
C2—C1—C7	123.3 (2)	C10—C11—C12	119.7 (2)
C6—C1—C7	118.2 (2)	O4—C12—C13	122.9 (2)
O1—C2—C3	117.6 (2)	O4—C12—C11	117.4 (2)
O1—C2—C1	122.3 (2)	C13—C12—C11	119.7 (2)
C3—C2—C1	120.0 (3)	C12—C13—C14	120.6 (2)
C4—C3—C2	120.4 (3)	C12—C13—H13	119.7
C4—C3—H3	119.8	C14—C13—H13	119.7
C2—C3—H3	119.8	C9—C14—C13	120.2 (2)
C3—C4—C5	119.7 (3)	C9—C14—H14	119.9
C3—C4—H4A	120.1	C13—C14—H14	119.9
C5—C4—H4A	120.1	O3—C15—H15A	109.5
C6—C5—C4	120.9 (3)	O3—C15—H15B	109.5
C6—C5—Br1	119.1 (2)	H15A—C15—H15B	109.5
C4—C5—Br1	119.9 (2)	O3—C15—H15C	109.5
C5—C6—C1	120.3 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.8	H15B—C15—H15C	109.5
C1—C6—H6	119.8	O5—C16—H16A	109.5
N1—C7—C1	122.5 (2)	O5—C16—H16B	109.5
N1—C7—H7	118.7	H16A—C16—H16B	109.5
C1—C7—H7	118.7	O5—C16—H16C	109.5
O2—C8—N2	121.7 (2)	H16A—C16—H16C	109.5
O2—C8—C9	122.1 (2)	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.89 (1)	2.07 (1)	2.949 (3)	167 (3)
O1—H1···N1	0.82	1.98	2.686 (3)	145
O4—H4···O2ⁱ	0.82	1.87	2.671 (3)	166
O5—H5···O3ⁱⁱ	0.82	2.46	3.125 (3)	139
O5—H5···O4ⁱⁱ	0.82	2.57	3.252 (3)	141

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₄·CH₄O
M_r	397.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.4412 (4), 17.5287 (9), 12.5555 (8)
β (°)	91.200 (3)
V (Å³)	1637.31 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.54
Crystal size (mm)	0.27 × 0.23 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.547, 0.593
No. of measured, independent and observed [I > 2σ(I)] reflections	9411, 3368, 2230
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.082, 1.01
No. of reflections	3368
No. of parameters	225
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.89 (1)	2.07 (1)	2.949 (3)	167 (3)
O1—H1···N1	0.82	1.98	2.686 (3)	145
O4—H4···O2ⁱ	0.82	1.87	2.671 (3)	166
O5—H5···O3ⁱⁱ	0.82	2.46	3.125 (3)	139
O5—H5···O4ⁱⁱ	0.82	2.57	3.252 (3)	141

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

The authors acknowledge Taizhou University for financial support.

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Volume 66| Part 7| July 2010| Page o1662

doi:10.1107/S1600536810022063

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-(5-Bromo-2-hy­dr­oxy­benzyl­­idene)-4-hy­dr­oxy-3-meth­­oxy­benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-(5-Bromo-2-hydroxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide methanol solvate