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

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ISSN: 2056-9890

N′-(2,4-Di­meth­oxy­benzyl­­idene)-3,4,5-tri­hydroxy­benzohydrazide ethanol solvate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Molecular Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: hapipah@um.edu.my

(Received 30 April 2009; accepted 19 May 2009; online 23 May 2009)

The title compound, C16H16N2O6·C2H5OH, was synthesized from 3,4,5-trihydroxy­benzoyl­hydrazide and 2,4-dimethoxy­benzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydr­oxy groups are involved in both intra­molecular O—H⋯O and inter­molecular O—H⋯N and O—H⋯O hydrogen bonds and a C—H⋯O interaction also occurs.

Related literature

For related compounds, see Abdul Alhadi et al. (2009[Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o909.]). For the parent N′-(2-hydroxy­benzyl­idene)benzohydrazide, see Lyubchova et al. (1995[Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893-1895.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O6·C2H6O

  • Mr = 378.38

  • Monoclinic, P 21 /n

  • a = 7.8347 (1) Å

  • b = 17.5412 (3) Å

  • c = 13.0230 (2) Å

  • β = 93.936 (1)°

  • V = 1785.53 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 K

  • 0.31 × 0.16 × 0.12 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.987

  • 19580 measured reflections

  • 5188 independent reflections

  • 3586 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.121

  • S = 1.02

  • 5188 reflections

  • 253 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O3 0.84 2.54 2.9325 (13) 109
O3—H3⋯O2 0.84 2.54 2.9325 (13) 110
O4—H4⋯O3 0.84 2.25 2.7009 (14) 114
N1—H1′⋯O7i 0.88 2.04 2.8844 (15) 160
O2—H2⋯O1ii 0.84 1.86 2.6871 (13) 170
O2—H2⋯N2ii 0.84 2.57 2.9293 (15) 107
O3—H3⋯O1ii 0.84 1.88 2.7200 (13) 177
O4—H4⋯O6iii 0.84 2.14 2.7366 (14) 127
C14—H14⋯O2iv 0.95 2.42 3.3539 (17) 167
Symmetry codes: (i) x, y-1, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) x+1, y, z+1; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

For related compounds, see Abdul Alhadi et al. (2009). For the parent N'-(2-hydroxybenzylidene)benzohydrazide, see Lyubchova et al. (1995).

Experimental top

A mixture of 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde were heated in ethanol (50 ml) for 12 h. The yellow crystals were obtained by recrystallization from ethanol.

Refinement top

All H atoms were placed at calculated positions (C— H 0.95 - 0.99, N—H 0.88, and O—H 0.84 Å) with Uiso(H) set to 1.2 - 1.5times Ueq (C,N,O)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H16N2O6.C2H5OH at 70% probability level. Hydrogen atoms are drawn as sphere of arbitrary radius.
N'-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide ethanol solvate top
Crystal data top
C16H16N2O6·C2H6OF(000) = 800
Mr = 378.38Dx = 1.408 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3445 reflections
a = 7.8347 (1) Åθ = 2.8–29.1°
b = 17.5412 (3) ŵ = 0.11 mm1
c = 13.0230 (2) ÅT = 100 K
β = 93.936 (1)°Block, yellow
V = 1785.53 (5) Å30.31 × 0.16 × 0.12 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5188 independent reflections
Radiation source: fine-focus sealed tube3586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 30.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.967, Tmax = 0.987k = 2424
19580 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0566P)2 + 0.3538P]
where P = (Fo2 + 2Fc2)/3
5188 reflections(Δ/σ)max = 0.001
253 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C16H16N2O6·C2H6OV = 1785.53 (5) Å3
Mr = 378.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.8347 (1) ŵ = 0.11 mm1
b = 17.5412 (3) ÅT = 100 K
c = 13.0230 (2) Å0.31 × 0.16 × 0.12 mm
β = 93.936 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5188 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3586 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.987Rint = 0.041
19580 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.02Δρmax = 0.41 e Å3
5188 reflectionsΔρmin = 0.27 e Å3
253 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
xyzUiso*/Ueq
C11.15941 (17)0.21466 (7)0.76768 (10)0.0156 (3)
H11.14580.25830.72480.019*
C21.25203 (17)0.22016 (7)0.86245 (10)0.0153 (3)
C31.26837 (17)0.15678 (8)0.92716 (10)0.0154 (3)
C41.19696 (18)0.08744 (8)0.89317 (10)0.0170 (3)
C51.10756 (18)0.08150 (8)0.79830 (10)0.0176 (3)
H51.06050.03390.77600.021*
C61.08672 (17)0.14571 (7)0.73529 (10)0.0154 (3)
C70.98683 (17)0.14395 (8)0.63409 (10)0.0159 (3)
C80.74521 (17)0.00842 (8)0.49550 (10)0.0168 (3)
H80.75390.02960.54760.023 (4)*
C90.64100 (17)0.00596 (8)0.40063 (10)0.0165 (3)
C100.57036 (17)0.07846 (8)0.38154 (10)0.0163 (3)
C110.47202 (17)0.09404 (8)0.29061 (10)0.0172 (3)
H110.42360.14310.27850.021*
C120.44633 (18)0.03640 (8)0.21828 (11)0.0188 (3)
C130.51352 (19)0.03637 (8)0.23587 (11)0.0209 (3)
H130.49390.07540.18590.025*
C140.60860 (18)0.05093 (8)0.32640 (11)0.0190 (3)
H140.65330.10070.33890.023*
C150.2879 (2)0.11915 (8)0.09897 (11)0.0227 (3)
H15A0.38240.15570.09780.034*
H15B0.22700.11690.03070.034*
H15C0.20870.13540.14980.034*
C160.5321 (2)0.20516 (8)0.44383 (12)0.0247 (3)
H16A0.40720.20070.43580.037*
H16B0.56470.23640.50440.037*
H16C0.57370.22920.38240.037*
C170.7901 (2)0.81507 (9)0.72385 (14)0.0313 (4)
H19A0.69290.83700.68260.047*
H19B0.74820.78660.78180.047*
H19C0.85310.78060.68090.047*
C180.9073 (2)0.87827 (9)0.76416 (12)0.0259 (3)
H18A0.84580.91100.81130.031*
H18B1.00740.85590.80380.031*
N10.92094 (15)0.07647 (6)0.60343 (9)0.0168 (2)
H1'0.93790.03570.64220.030 (5)*
N20.82556 (15)0.07168 (6)0.50974 (9)0.0174 (2)
O10.96209 (13)0.20261 (5)0.58110 (7)0.0219 (2)
O21.32670 (14)0.28879 (5)0.88620 (7)0.0218 (2)
H21.35690.29010.94930.033*
O31.35316 (13)0.15568 (6)1.02261 (7)0.0209 (2)
H31.38770.19981.03810.031*
O41.21299 (15)0.02350 (6)0.95174 (8)0.0273 (3)
H41.27180.03321.00650.041*
O50.60584 (13)0.13118 (6)0.45673 (7)0.0224 (2)
O60.35424 (14)0.04532 (6)0.12604 (8)0.0264 (3)
O70.96498 (14)0.92367 (6)0.68270 (8)0.0229 (2)
H71.02910.89750.64750.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0190 (6)0.0138 (6)0.0137 (6)0.0025 (5)0.0015 (5)0.0010 (5)
C20.0187 (6)0.0123 (6)0.0148 (6)0.0006 (5)0.0000 (5)0.0015 (5)
C30.0175 (6)0.0163 (6)0.0119 (6)0.0006 (5)0.0021 (5)0.0010 (5)
C40.0214 (7)0.0143 (6)0.0147 (6)0.0000 (5)0.0029 (5)0.0027 (5)
C50.0223 (7)0.0140 (6)0.0159 (7)0.0007 (5)0.0034 (5)0.0003 (5)
C60.0171 (6)0.0156 (6)0.0131 (6)0.0011 (5)0.0020 (5)0.0006 (5)
C70.0175 (6)0.0157 (6)0.0141 (6)0.0019 (5)0.0016 (5)0.0005 (5)
C80.0194 (7)0.0158 (6)0.0148 (6)0.0008 (5)0.0021 (5)0.0007 (5)
C90.0170 (6)0.0168 (6)0.0151 (7)0.0002 (5)0.0021 (5)0.0009 (5)
C100.0187 (7)0.0162 (6)0.0139 (6)0.0010 (5)0.0010 (5)0.0013 (5)
C110.0188 (7)0.0162 (6)0.0161 (6)0.0014 (5)0.0020 (5)0.0015 (5)
C120.0201 (7)0.0192 (7)0.0162 (7)0.0000 (5)0.0059 (5)0.0012 (5)
C130.0274 (8)0.0156 (6)0.0186 (7)0.0001 (6)0.0065 (6)0.0026 (5)
C140.0208 (7)0.0141 (6)0.0212 (7)0.0009 (5)0.0040 (5)0.0008 (5)
C150.0287 (8)0.0186 (7)0.0197 (7)0.0034 (6)0.0074 (6)0.0025 (6)
C160.0339 (8)0.0158 (7)0.0236 (8)0.0045 (6)0.0042 (6)0.0033 (6)
C170.0369 (9)0.0197 (7)0.0381 (10)0.0044 (7)0.0079 (7)0.0009 (7)
C180.0344 (8)0.0217 (7)0.0212 (7)0.0002 (6)0.0020 (6)0.0049 (6)
N10.0215 (6)0.0151 (5)0.0129 (5)0.0010 (4)0.0063 (4)0.0013 (4)
N20.0199 (6)0.0172 (6)0.0142 (6)0.0000 (5)0.0064 (4)0.0011 (4)
O10.0323 (6)0.0142 (5)0.0176 (5)0.0012 (4)0.0101 (4)0.0016 (4)
O20.0353 (6)0.0145 (5)0.0145 (5)0.0057 (4)0.0070 (4)0.0012 (4)
O30.0310 (6)0.0167 (5)0.0137 (5)0.0028 (4)0.0079 (4)0.0011 (4)
O40.0446 (7)0.0167 (5)0.0184 (5)0.0065 (5)0.0141 (5)0.0056 (4)
O50.0320 (6)0.0162 (5)0.0177 (5)0.0042 (4)0.0076 (4)0.0030 (4)
O60.0382 (6)0.0176 (5)0.0209 (5)0.0043 (4)0.0160 (5)0.0010 (4)
O70.0295 (6)0.0163 (5)0.0232 (6)0.0001 (4)0.0034 (4)0.0001 (4)
Geometric parameters (Å, º) top
C1—C61.3900 (18)C13—C141.3745 (19)
C1—C21.3914 (18)C13—H130.9500
C1—H10.9500C14—H140.9500
C2—O21.3647 (15)C15—O61.4308 (16)
C2—C31.3958 (18)C15—H15A0.9800
C3—O31.3687 (15)C15—H15B0.9800
C3—C41.3979 (18)C15—H15C0.9800
C4—O41.3574 (16)C16—O51.4258 (17)
C4—C51.3818 (18)C16—H16A0.9800
C5—C61.3965 (18)C16—H16B0.9800
C5—H50.9500C16—H16C0.9800
C6—C71.4862 (18)C17—C181.511 (2)
C7—O11.2466 (16)C17—H19A0.9800
C7—N11.3412 (17)C17—H19B0.9800
C8—N21.2830 (17)C17—H19C0.9800
C8—C91.4554 (18)C18—O71.4247 (18)
C8—H80.9500C18—H18A0.9900
C9—C141.4004 (19)C18—H18B0.9900
C9—C101.4023 (18)N1—N21.3889 (15)
C10—O51.3615 (16)N1—H1'0.8800
C10—C111.3948 (18)O2—H20.8400
C11—C121.3869 (19)O3—H30.8400
C11—H110.9500O4—H40.8400
C12—O61.3672 (16)O7—H70.8400
C12—C131.3938 (19)
C6—C1—C2120.50 (12)C12—C13—H13120.4
C6—C1—H1119.8C13—C14—C9121.44 (13)
C2—C1—H1119.8C13—C14—H14119.3
O2—C2—C1116.85 (12)C9—C14—H14119.3
O2—C2—C3123.07 (11)O6—C15—H15A109.5
C1—C2—C3120.06 (12)O6—C15—H15B109.5
O3—C3—C2125.32 (12)H15A—C15—H15B109.5
O3—C3—C4115.73 (11)O6—C15—H15C109.5
C2—C3—C4118.93 (11)H15A—C15—H15C109.5
O4—C4—C5117.51 (12)H15B—C15—H15C109.5
O4—C4—C3121.43 (12)O5—C16—H16A109.5
C5—C4—C3121.07 (12)O5—C16—H16B109.5
C4—C5—C6119.75 (12)H16A—C16—H16B109.5
C4—C5—H5120.1O5—C16—H16C109.5
C6—C5—H5120.1H16A—C16—H16C109.5
C1—C6—C5119.63 (12)H16B—C16—H16C109.5
C1—C6—C7117.84 (11)C18—C17—H19A109.5
C5—C6—C7122.52 (12)C18—C17—H19B109.5
O1—C7—N1121.44 (12)H19A—C17—H19B109.5
O1—C7—C6121.75 (12)C18—C17—H19C109.5
N1—C7—C6116.79 (12)H19A—C17—H19C109.5
N2—C8—C9120.91 (12)H19B—C17—H19C109.5
N2—C8—H8119.5O7—C18—C17111.58 (13)
C9—C8—H8119.5O7—C18—H18A109.3
C14—C9—C10118.24 (12)C17—C18—H18A109.3
C14—C9—C8121.81 (12)O7—C18—H18B109.3
C10—C9—C8119.95 (12)C17—C18—H18B109.3
O5—C10—C11123.45 (12)H18A—C18—H18B108.0
O5—C10—C9115.45 (11)C7—N1—N2119.19 (11)
C11—C10—C9121.09 (12)C7—N1—H1'120.4
C12—C11—C10118.67 (12)N2—N1—H1'120.4
C12—C11—H11120.7C8—N2—N1114.10 (11)
C10—C11—H11120.7C2—O2—H2109.5
O6—C12—C11123.82 (12)C3—O3—H3109.5
O6—C12—C13114.82 (12)C4—O4—H4109.5
C11—C12—C13121.36 (12)C10—O5—C16118.18 (11)
C14—C13—C12119.17 (13)C12—O6—C15118.75 (11)
C14—C13—H13120.4C18—O7—H7109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.842.542.9325 (13)109
O3—H3···O20.842.542.9325 (13)110
O4—H4···O30.842.252.7009 (14)114
N1—H1···O7i0.882.042.8844 (15)160
O2—H2···O1ii0.841.862.6871 (13)170
O2—H2···N2ii0.842.572.9293 (15)107
O3—H3···O1ii0.841.882.7200 (13)177
O4—H4···O6iii0.842.142.7366 (14)127
C14—H14···O2iv0.952.423.3539 (17)167
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H16N2O6·C2H6O
Mr378.38
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)7.8347 (1), 17.5412 (3), 13.0230 (2)
β (°) 93.936 (1)
V3)1785.53 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.31 × 0.16 × 0.12
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.967, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
19580, 5188, 3586
Rint0.041
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.121, 1.02
No. of reflections5188
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.842.542.9325 (13)109.4
O3—H3···O20.842.542.9325 (13)109.8
O4—H4···O30.842.252.7009 (14)114.2
N1—H1'···O7i0.882.042.8844 (15)160
O2—H2···O1ii0.841.862.6871 (13)169.7
O2—H2···N2ii0.842.572.9293 (15)107.4
O3—H3···O1ii0.841.882.7200 (13)176.5
O4—H4···O6iii0.842.142.7366 (14)127.3
C14—H14···O2iv0.952.423.3539 (17)166.5
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y, z+1; (iv) x1/2, y+1/2, z1/2.
 

Acknowledgements

The authors thank the University of Malaya for funding this study (Science Fund Grant 12-0-03-2031, 12-02-03-2051 and PJP FS350-2008)

References

First citationAbdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o909.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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