Crystal structure of (E)-4-hy­droxy-N′-(3-hy­droxy­benzyl­idene)benzohydrazide monohydrate

Harrison, W.T.A.; Low, J.N.; Wardell, J.L.

doi:10.1107/S1600536814011908

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o891-o892

doi:10.1107/S1600536814011908

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Crystal structure of (E)-4-hydroxy-N′-(3-hydroxybenzylidene)benzohydrazide monohydrate

William T. A. Harrison,^a ^* John Nicolson Low ^a and James L. Wardell ^a,^b

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^bFioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: w.harrison@abdn.ac.uk

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 May 2014; accepted 22 May 2014; online 1 August 2014)

In the title benzohydrazide hydrate, C₁₄H₁₂N₂O₃·H₂O, the dihedral angle between the aromatic rings is 58.11 (6)° and the C=O and N—H groups adopt an anti orientation. The main twist in the molecule occurs about the C(=O)—C_ar (ar = aromatic) bond, with an N—C(=O)—C_ar—C_ar torsion angle of −43.5 (2)°. In the crystal, the components are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. These interactions generate [10-1] chains, with adjacent organic molecules linked by inversion symmetry generating either pairs of N—H⋯O links [R₂²(16) loops] or pairs of O—H⋯O links [R₂²(20) loops]. Pairs of water molecules are located in the R₂²(20) loops and form their own O—H⋯O and O—H⋯N hydrogen bonds to adjacent organic molecules in the chain. Finally, an interchain O—H⋯O hydrogen-bond link from the 4-hydroxy group generates (010) sheets.

Keywords: crystal structure; benzohydrazide; hydrate; hydrogen bonding.

CCDC reference: 1004470

1. Related literature

For a related structure, see: Fun et al. (2011 ). A survey of the Cambridge Structural Database (Version 5.35 of November 2013; Allen, 2002 ) revealed no fewer than 581 distinct benzohydrazide fragments with different substituents on the aromatic rings and/or other chemical species in the crystal: all bond lengths for the central fragment of the title compound lie close to the mean values for these structures. The only parameter in the metrical survey that shows significant variation is the dihedral angle between the aromatic rings, with the most common value close to zero, and a roughly linear decrease to 90°.

2. Experimental

2.1. Crystal data

C₁₄H₁₂N₂O₃·H₂O
M_r = 274.27
Triclinic, $[P \overline 1]$
a = 7.1826 (5) Å
b = 9.2043 (6) Å
c = 10.7568 (7) Å
α = 91.847 (7)°
β = 102.433 (7)°
γ = 110.191 (8)°
V = 647.37 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.09 × 0.05 × 0.02 mm

2.2. Data collection

Rigaku Saturn CCD diffractometer
8728 measured reflections
2962 independent reflections
2038 reflections with I > 2σ(I)
R_int = 0.049

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.105
S = 1.06
2962 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.922 (18)	2.044 (19)	2.9357 (19)	162.2 (16)
O1—H1O⋯O4ⁱⁱ	0.92 (2)	1.68 (2)	2.6025 (18)	172.6 (17)
O3—H3O⋯O2ⁱⁱⁱ	0.92 (2)	1.83 (2)	2.7512 (17)	178.1 (17)
O4—H1W⋯N2	0.86 (2)	2.16 (2)	3.018 (2)	172.5 (19)
O4—H2W⋯O2ⁱⁱⁱ	0.89 (2)	1.98 (2)	2.8676 (17)	170.5 (18)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2010 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1004470

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814011908/su0006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011908/su0006Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814011908/su0006Isup3.cml

checkCIF report

Synthesis and crystallization top

Equimolar quantities of 4-hydroxybenzohydrazide and 3-hydroxybenzaldehyde were refluxed in ethanol for several hours and then cooled to room temperature. Colourless chips of the title compound were obtained by slow evaporation of the solvent at room temperature after several days.

Refinement top

O- and N-bound H atoms were located in difference Fourier maps and their positions were freely refined. C-bound H atoms were placed in idealized positions (C—H = 0.93 Å) and refined as riding atoms. The constraint U_iso(H) = 1.2U_eq(carrier) was applied in all cases.

Related literature top

For a related structure, see: Fun et al. (2011). A survey of the Cambridge Structural Database (Version 5.35 of November 2013; Allen, 2002) revealed no fewer than 581 distinct benzohydrazide fragments with different substituents on the aromatic rings and/or other chemical species in the crystal: all bond lengths for the central fragment of the title compound lie close to the mean values for these structures. The only parameter in the metrical survey that shows significant variation is the dihedral angle between the aromatic rings, with the most common value close to zero, and a roughly linear decrease to 90°.

Computing details top

Data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear (Rigaku, 2010); data reduction: CrystalClear (Rigaku, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the asymmetric unit of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A fragment of a [101] chain in the structure of the title compound, with hydrogen bonds shown as double-dashed lines, showing the R₂²(16) loops and R₂²(20) loops between adjacent organic molecules (see Table 2 for details of the hydrogen bonding and the symmetry codes).
	Fig. 3. A histogram of dihedral angles between the aromatic rings of benzohydrazide structures in the Cambridge Structural Database (Version 5.35; Allen, 2002).

(E)-4-Hydroxy-N'-(3-hydroxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₄H₁₂N₂O₃·H₂O	Z = 2
M_r = 274.27	F(000) = 288
Triclinic, P1	D_x = 1.407 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1826 (5) Å	Cell parameters from 6867 reflections
b = 9.2043 (6) Å	θ = 3.1–27.5°
c = 10.7568 (7) Å	µ = 0.11 mm⁻¹
α = 91.847 (7)°	T = 100 K
β = 102.433 (7)°	Chip, colourless
γ = 110.191 (8)°	0.09 × 0.05 × 0.02 mm
V = 647.37 (7) Å³

Data collection top

Rigaku Saturn CCD diffractometer	2038 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −9→9
8728 measured reflections	k = −11→11
2962 independent reflections	l = −13→13

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0374P)² + 0.144P] where P = (F_o² + 2F_c²)/3
2962 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₃·H₂O	γ = 110.191 (8)°
M_r = 274.27	V = 647.37 (7) Å³
Triclinic, P1	Z = 2
a = 7.1826 (5) Å	Mo Kα radiation
b = 9.2043 (6) Å	µ = 0.11 mm⁻¹
c = 10.7568 (7) Å	T = 100 K
α = 91.847 (7)°	0.09 × 0.05 × 0.02 mm
β = 102.433 (7)°

Data collection top

Rigaku Saturn CCD diffractometer	2038 reflections with I > 2σ(I)
8728 measured reflections	R_int = 0.049
2962 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
2962 reflections	Δρ_min = −0.28 e Å⁻³
196 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
C1	0.2487 (2)	0.51249 (18)	0.02953 (16)	0.0151 (4)
H1	0.2596	0.6145	0.0499	0.018*
C2	0.2488 (2)	0.46303 (18)	−0.09366 (16)	0.0149 (4)
H2	0.2560	0.5306	−0.1564	0.018*
C3	0.2379 (2)	0.31187 (19)	−0.12226 (15)	0.0140 (4)
C4	0.2225 (2)	0.20863 (19)	−0.02998 (16)	0.0150 (4)
H4	0.2163	0.1077	−0.0499	0.018*
C5	0.2167 (2)	0.25738 (18)	0.09144 (16)	0.0145 (4)
H5	0.2022	0.1879	0.1527	0.017*
C6	0.2325 (2)	0.41045 (18)	0.12303 (15)	0.0133 (4)
C7	0.2265 (3)	0.45636 (18)	0.25514 (16)	0.0140 (4)
C8	0.5163 (3)	0.77584 (19)	0.48276 (16)	0.0164 (4)
H8	0.6243	0.8109	0.4432	0.020*
C9	0.5316 (3)	0.85792 (18)	0.60520 (16)	0.0145 (4)
C10	0.3753 (3)	0.80721 (18)	0.66983 (16)	0.0148 (4)
H10	0.2637	0.7159	0.6379	0.018*
C11	0.3865 (3)	0.89243 (18)	0.78093 (16)	0.0154 (4)
C12	0.5575 (3)	1.02744 (18)	0.83137 (16)	0.0158 (4)
H12	0.5659	1.0846	0.9066	0.019*
C13	0.7134 (3)	1.07503 (18)	0.76867 (16)	0.0162 (4)
H13	0.8278	1.1638	0.8029	0.019*
C14	0.7017 (3)	0.99231 (18)	0.65541 (16)	0.0167 (4)
H14	0.8066	1.0262	0.6132	0.020*
N1	0.3623 (2)	0.59830 (16)	0.30909 (13)	0.0156 (3)
H1N	0.469 (3)	0.647 (2)	0.2723 (17)	0.019*
N2	0.3584 (2)	0.65697 (15)	0.42830 (13)	0.0153 (3)
O1	0.24457 (19)	0.25851 (13)	−0.24143 (11)	0.0173 (3)
H1O	0.195 (3)	0.309 (2)	−0.3059 (19)	0.021*
O2	0.10482 (18)	0.37043 (13)	0.31151 (11)	0.0177 (3)
O3	0.23698 (19)	0.84893 (14)	0.84718 (12)	0.0198 (3)
H3O	0.125 (3)	0.776 (2)	0.7930 (18)	0.024*
O4	−0.0770 (2)	0.61780 (16)	0.42664 (13)	0.0236 (3)
H1W	0.047 (3)	0.624 (2)	0.4329 (19)	0.028*
H2W	−0.101 (3)	0.615 (2)	0.505 (2)	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0145 (8)	0.0140 (8)	0.0159 (9)	0.0042 (7)	0.0031 (7)	0.0012 (7)
C2	0.0147 (9)	0.0163 (8)	0.0138 (9)	0.0055 (7)	0.0035 (7)	0.0049 (7)
C3	0.0122 (8)	0.0206 (8)	0.0095 (8)	0.0067 (7)	0.0024 (6)	0.0007 (7)
C4	0.0157 (9)	0.0157 (8)	0.0140 (9)	0.0073 (7)	0.0021 (7)	0.0004 (7)
C5	0.0147 (8)	0.0154 (8)	0.0127 (9)	0.0047 (7)	0.0028 (7)	0.0046 (7)
C6	0.0117 (8)	0.0173 (8)	0.0111 (8)	0.0056 (7)	0.0021 (6)	0.0014 (6)
C7	0.0149 (8)	0.0163 (8)	0.0129 (9)	0.0081 (7)	0.0029 (7)	0.0024 (7)
C8	0.0164 (9)	0.0175 (8)	0.0164 (9)	0.0062 (7)	0.0057 (7)	0.0025 (7)
C9	0.0171 (9)	0.0139 (8)	0.0116 (9)	0.0058 (7)	0.0017 (7)	0.0015 (6)
C10	0.0164 (9)	0.0138 (8)	0.0124 (9)	0.0040 (7)	0.0019 (7)	0.0011 (7)
C11	0.0166 (9)	0.0168 (8)	0.0150 (9)	0.0076 (7)	0.0050 (7)	0.0048 (7)
C12	0.0194 (9)	0.0151 (8)	0.0120 (9)	0.0067 (7)	0.0014 (7)	−0.0009 (7)
C13	0.0159 (9)	0.0133 (8)	0.0167 (9)	0.0042 (7)	0.0001 (7)	0.0017 (7)
C14	0.0155 (9)	0.0174 (8)	0.0176 (9)	0.0062 (7)	0.0041 (7)	0.0055 (7)
N1	0.0175 (8)	0.0176 (7)	0.0117 (7)	0.0043 (6)	0.0071 (6)	0.0008 (6)
N2	0.0207 (8)	0.0176 (7)	0.0091 (7)	0.0081 (6)	0.0051 (6)	−0.0002 (6)
O1	0.0219 (7)	0.0225 (6)	0.0098 (6)	0.0104 (5)	0.0044 (5)	0.0018 (5)
O2	0.0195 (7)	0.0190 (6)	0.0136 (6)	0.0039 (5)	0.0068 (5)	0.0010 (5)
O3	0.0181 (7)	0.0203 (6)	0.0164 (7)	0.0001 (5)	0.0070 (5)	−0.0041 (5)
O4	0.0222 (7)	0.0391 (8)	0.0145 (7)	0.0154 (6)	0.0069 (6)	0.0081 (6)

Geometric parameters (Å, º) top

C1—C2	1.387 (2)	C9—C14	1.394 (2)
C1—C6	1.394 (2)	C9—C10	1.399 (2)
C1—H1	0.9300	C10—C11	1.380 (2)
C2—C3	1.387 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—O3	1.3685 (19)
C3—O1	1.3743 (19)	C11—C12	1.401 (2)
C3—C4	1.391 (2)	C12—C13	1.381 (2)
C4—C5	1.381 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.387 (2)
C5—C6	1.398 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.483 (2)	N1—N2	1.3847 (18)
C7—O2	1.2404 (19)	N1—H1N	0.922 (18)
C7—N1	1.350 (2)	O1—H1O	0.92 (2)
C8—N2	1.281 (2)	O3—H3O	0.92 (2)
C8—C9	1.461 (2)	O4—H1W	0.86 (2)
C8—H8	0.9300	O4—H2W	0.89 (2)

C2—C1—C6	120.52 (15)	C14—C9—C8	119.08 (15)
C2—C1—H1	119.7	C10—C9—C8	121.08 (14)
C6—C1—H1	119.7	C11—C10—C9	120.12 (15)
C3—C2—C1	119.34 (15)	C11—C10—H10	119.9
C3—C2—H2	120.3	C9—C10—H10	119.9
C1—C2—H2	120.3	O3—C11—C10	122.49 (15)
O1—C3—C2	121.75 (15)	O3—C11—C12	117.45 (15)
O1—C3—C4	117.34 (15)	C10—C11—C12	120.05 (15)
C2—C3—C4	120.90 (15)	C13—C12—C11	119.56 (15)
C5—C4—C3	119.41 (15)	C13—C12—H12	120.2
C5—C4—H4	120.3	C11—C12—H12	120.2
C3—C4—H4	120.3	C12—C13—C14	120.89 (15)
C4—C5—C6	120.53 (15)	C12—C13—H13	119.6
C4—C5—H5	119.7	C14—C13—H13	119.6
C6—C5—H5	119.7	C13—C14—C9	119.56 (15)
C1—C6—C5	119.25 (15)	C13—C14—H14	120.2
C1—C6—C7	122.63 (15)	C9—C14—H14	120.2
C5—C6—C7	118.11 (15)	C7—N1—N2	119.60 (14)
O2—C7—N1	122.60 (15)	C7—N1—H1N	119.1 (11)
O2—C7—C6	122.25 (14)	N2—N1—H1N	120.5 (11)
N1—C7—C6	115.15 (14)	C8—N2—N1	114.82 (14)
N2—C8—C9	121.91 (15)	C3—O1—H1O	112.8 (11)
N2—C8—H8	119.0	C11—O3—H3O	106.5 (11)
C9—C8—H8	119.0	H1W—O4—H2W	108.6 (18)
C14—C9—C10	119.79 (15)

C6—C1—C2—C3	−1.7 (2)	N2—C8—C9—C10	1.6 (3)
C1—C2—C3—O1	−177.71 (15)	C14—C9—C10—C11	1.9 (3)
C1—C2—C3—C4	1.4 (2)	C8—C9—C10—C11	−175.61 (16)
O1—C3—C4—C5	179.58 (14)	C9—C10—C11—O3	179.33 (16)
C2—C3—C4—C5	0.4 (2)	C9—C10—C11—C12	−1.9 (3)
C3—C4—C5—C6	−2.0 (2)	O3—C11—C12—C13	179.29 (16)
C2—C1—C6—C5	0.2 (2)	C10—C11—C12—C13	0.5 (3)
C2—C1—C6—C7	−178.43 (15)	C11—C12—C13—C14	1.0 (3)
C4—C5—C6—C1	1.7 (2)	C12—C13—C14—C9	−1.0 (3)
C4—C5—C6—C7	−179.64 (15)	C10—C9—C14—C13	−0.4 (3)
C1—C6—C7—O2	136.31 (18)	C8—C9—C14—C13	177.13 (15)
C5—C6—C7—O2	−42.3 (2)	O2—C7—N1—N2	−4.7 (3)
C1—C6—C7—N1	−43.5 (2)	C6—C7—N1—N2	175.08 (14)
C5—C6—C7—N1	137.90 (16)	C9—C8—N2—N1	176.21 (15)
N2—C8—C9—C14	−175.95 (16)	C7—N1—N2—C8	166.42 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.922 (18)	2.044 (19)	2.9357 (19)	162.2 (16)
O1—H1O···O4ⁱⁱ	0.92 (2)	1.68 (2)	2.6025 (18)	172.6 (17)
O3—H3O···O2ⁱⁱⁱ	0.92 (2)	1.83 (2)	2.7512 (17)	178.1 (17)
O4—H1W···N2	0.86 (2)	2.16 (2)	3.018 (2)	172.5 (19)
O4—H2W···O2ⁱⁱⁱ	0.89 (2)	1.98 (2)	2.8676 (17)	170.5 (18)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.922 (18)	2.044 (19)	2.9357 (19)	162.2 (16)
O1—H1O···O4ⁱⁱ	0.92 (2)	1.68 (2)	2.6025 (18)	172.6 (17)
O3—H3O···O2ⁱⁱⁱ	0.92 (2)	1.83 (2)	2.7512 (17)	178.1 (17)
O4—H1W···N2	0.86 (2)	2.16 (2)	3.018 (2)	172.5 (19)
O4—H2W···O2ⁱⁱⁱ	0.89 (2)	1.98 (2)	2.8676 (17)	170.5 (18)

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

Acknowledgements

The authors thank the National Crystallography Service (University of Southampton) for the data collection.

References

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o891-o892

doi:10.1107/S1600536814011908

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

Crystal structure of (E)-4-hy­dr­oxy-N′-(3-hy­dr­oxy­benzyl­­idene)benzohydrazide monohydrate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-4-hydroxy-N′-(3-hydroxybenzylidene)benzohydrazide monohydrate