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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-4-Hydr­­oxy-N′-(2-hydr­­oxy-4-meth­oxy­benzyl­­idene)benzohydrazide N,N-di­methyl­formamide solvate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 16 December 2008; online 20 December 2008)

The Schiff base mol­ecule of the title compound, C15H14N2O4·C3H7NO, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is nearly planar (r.m.s. deviation 0.20 Å). The amido N atom is a hydrogen-bond donor to the dimethyl­formamide solvate mol­ecule. One of the hydr­oxy groups forms an intra­molecular hydrogen bond to the N atom of the C=N double bond, whereas the other forms an inter­molecular hydrogen bond to the carbonyl group.

Related literature

For the corresponding monohydrate, see: Lair et al. (2009[Lair, N. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o189.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O4·C3H7NO

  • Mr = 359.38

  • Monoclinic, P 21 /c

  • a = 11.8273 (2) Å

  • b = 7.8206 (2) Å

  • c = 19.4218 (3) Å

  • β = 103.674 (1)°

  • V = 1745.53 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 (2) K

  • 0.30 × 0.25 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 11825 measured reflections

  • 4003 independent reflections

  • 3303 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.104

  • S = 1.01

  • 4003 reflections

  • 240 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O2i 0.84 1.82 2.656 (1) 174
O3—H3o⋯N2 0.84 1.87 2.607 (1) 145
N1—H1n⋯O5 0.88 1.95 2.787 (1) 157
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For thecorresponding monohydrate, see: Lair et al. (2009).

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (0.30 g, 2 mmol) and 4-hydroxybenzohydrazide (0.30 g, 2 mmol) were heated in an ethanol-methanol mixture (50 ml) for 2 hours. The solvent was removed and the resulting compound recrystallized from DMF.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98, N–H 0.88, O–H 0.84 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times 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, 2009).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Packing diagram with hydrogen bonds drawn as dashed lines.
(E)-4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide N,N-dimethylformamide solvate top
Crystal data top
C15H14N2O4·C3H7NOF(000) = 760
Mr = 359.38Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4180 reflections
a = 11.8273 (2) Åθ = 2.2–28.3°
b = 7.8206 (2) ŵ = 0.10 mm1
c = 19.4218 (3) ÅT = 100 K
β = 103.674 (1)°Prism, colorless
V = 1745.53 (6) Å30.30 × 0.25 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
3303 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω scansh = 1514
11825 measured reflectionsk = 108
4003 independent reflectionsl = 2525
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0515P)2 + 0.678P]
where P = (Fo2 + 2Fc2)/3
4003 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C15H14N2O4·C3H7NOV = 1745.53 (6) Å3
Mr = 359.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8273 (2) ŵ = 0.10 mm1
b = 7.8206 (2) ÅT = 100 K
c = 19.4218 (3) Å0.30 × 0.25 × 0.15 mm
β = 103.674 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3303 reflections with I > 2σ(I)
11825 measured reflectionsRint = 0.023
4003 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.01Δρmax = 0.29 e Å3
4003 reflectionsΔρmin = 0.22 e Å3
240 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.66809 (8)0.74503 (12)0.66928 (5)0.0199 (2)
H1O0.69790.76760.71200.030*
O20.22303 (8)0.32357 (12)0.69867 (4)0.0211 (2)
O30.04810 (8)0.04690 (13)0.62396 (5)0.0228 (2)
H3O0.00690.11610.62590.034*
O40.40063 (8)0.13116 (12)0.47806 (5)0.0200 (2)
O50.18144 (8)0.46309 (12)0.44318 (5)0.0227 (2)
N10.17427 (9)0.37007 (14)0.58062 (5)0.0170 (2)
H1N0.18880.42170.54340.020*
N20.07635 (9)0.27015 (14)0.57472 (5)0.0173 (2)
N30.16184 (11)0.57465 (17)0.33359 (6)0.0285 (3)
C10.35639 (10)0.48355 (16)0.64886 (6)0.0154 (2)
C20.41943 (11)0.53743 (17)0.71534 (6)0.0188 (3)
H20.39010.51460.75590.023*
C30.52370 (11)0.62336 (17)0.72326 (7)0.0197 (3)
H30.56560.65840.76900.024*
C40.56747 (11)0.65871 (16)0.66420 (6)0.0164 (3)
C50.50566 (11)0.60607 (16)0.59728 (6)0.0179 (3)
H50.53510.62970.55680.022*
C60.40136 (11)0.51936 (16)0.58983 (6)0.0174 (3)
H60.35970.48370.54410.021*
C70.24710 (11)0.38628 (16)0.64518 (6)0.0162 (2)
C80.00648 (11)0.25971 (16)0.51315 (6)0.0170 (3)
H80.02280.32010.47420.020*
C90.09720 (10)0.15539 (16)0.50355 (6)0.0158 (2)
C100.12163 (11)0.05447 (16)0.55883 (6)0.0169 (3)
C110.22325 (11)0.04046 (16)0.54772 (6)0.0178 (3)
H110.23880.10900.58480.021*
C120.30237 (11)0.03528 (16)0.48223 (7)0.0169 (3)
C130.28026 (11)0.06116 (16)0.42650 (7)0.0183 (3)
H130.33410.06330.38170.022*
C140.17781 (11)0.15370 (16)0.43817 (6)0.0173 (3)
H140.16170.21860.40020.021*
C150.49470 (11)0.10776 (18)0.41743 (7)0.0208 (3)
H15A0.56430.16510.42520.031*
H15B0.47390.15680.37570.031*
H15C0.51050.01470.40980.031*
C160.21144 (11)0.56143 (17)0.40187 (7)0.0217 (3)
H160.27570.63430.42040.026*
C170.06495 (16)0.4656 (3)0.30112 (9)0.0449 (5)
H17A0.05020.38390.33620.067*
H17B0.08360.40330.26140.067*
H17C0.00450.53580.28370.067*
C180.20628 (17)0.6926 (3)0.28847 (10)0.0555 (6)
H18A0.27250.75580.31700.083*
H18B0.14480.77310.26650.083*
H18C0.23150.62830.25140.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0186 (4)0.0259 (5)0.0151 (4)0.0060 (4)0.0037 (3)0.0012 (4)
O20.0185 (4)0.0274 (5)0.0168 (4)0.0028 (4)0.0030 (3)0.0036 (4)
O30.0202 (5)0.0306 (6)0.0156 (4)0.0057 (4)0.0005 (4)0.0032 (4)
O40.0167 (4)0.0236 (5)0.0188 (4)0.0051 (4)0.0026 (4)0.0005 (4)
O50.0268 (5)0.0235 (5)0.0173 (4)0.0020 (4)0.0044 (4)0.0008 (4)
N10.0158 (5)0.0190 (5)0.0155 (5)0.0034 (4)0.0023 (4)0.0013 (4)
N20.0149 (5)0.0180 (5)0.0191 (5)0.0012 (4)0.0040 (4)0.0011 (4)
N30.0272 (6)0.0369 (7)0.0224 (6)0.0071 (5)0.0079 (5)0.0088 (5)
C10.0155 (6)0.0138 (6)0.0166 (6)0.0017 (5)0.0027 (5)0.0003 (4)
C20.0213 (6)0.0210 (7)0.0146 (6)0.0028 (5)0.0054 (5)0.0002 (5)
C30.0224 (6)0.0220 (7)0.0140 (6)0.0037 (5)0.0031 (5)0.0019 (5)
C40.0156 (6)0.0152 (6)0.0180 (6)0.0003 (5)0.0033 (5)0.0004 (5)
C50.0196 (6)0.0196 (6)0.0155 (6)0.0004 (5)0.0058 (5)0.0003 (5)
C60.0183 (6)0.0188 (6)0.0138 (6)0.0009 (5)0.0013 (5)0.0008 (5)
C70.0157 (6)0.0159 (6)0.0168 (6)0.0021 (5)0.0032 (5)0.0002 (5)
C80.0178 (6)0.0168 (6)0.0168 (6)0.0008 (5)0.0050 (5)0.0004 (5)
C90.0146 (6)0.0156 (6)0.0173 (6)0.0011 (5)0.0041 (5)0.0013 (5)
C100.0167 (6)0.0190 (6)0.0145 (6)0.0024 (5)0.0028 (5)0.0008 (5)
C110.0195 (6)0.0189 (6)0.0161 (6)0.0009 (5)0.0064 (5)0.0018 (5)
C120.0151 (6)0.0160 (6)0.0203 (6)0.0003 (5)0.0055 (5)0.0027 (5)
C130.0173 (6)0.0210 (7)0.0156 (6)0.0012 (5)0.0016 (5)0.0002 (5)
C140.0189 (6)0.0179 (6)0.0151 (6)0.0012 (5)0.0042 (5)0.0022 (5)
C150.0163 (6)0.0252 (7)0.0198 (6)0.0030 (5)0.0022 (5)0.0017 (5)
C160.0197 (6)0.0211 (7)0.0239 (6)0.0011 (5)0.0045 (5)0.0008 (5)
C170.0402 (10)0.0651 (13)0.0238 (8)0.0006 (9)0.0040 (7)0.0066 (8)
C180.0496 (11)0.0763 (15)0.0460 (11)0.0161 (10)0.0217 (9)0.0405 (10)
Geometric parameters (Å, º) top
O1—C41.3514 (15)C5—H50.9500
O1—H1O0.8400C6—H60.9500
O2—C71.2412 (15)C8—C91.4478 (17)
O3—C101.3565 (15)C8—H80.9500
O3—H3O0.8400C9—C141.3962 (17)
O4—C121.3693 (15)C9—C101.4162 (17)
O4—C151.4278 (15)C10—C111.3855 (17)
O5—C161.2229 (16)C11—C121.3901 (17)
N1—C71.3489 (15)C11—H110.9500
N1—N21.3791 (14)C12—C131.3938 (17)
N1—H1N0.8800C13—C141.3832 (17)
N2—C81.2855 (16)C13—H130.9500
N3—C161.3212 (17)C14—H140.9500
N3—C171.448 (2)C15—H15A0.9800
N3—C181.454 (2)C15—H15B0.9800
C1—C21.3948 (17)C15—H15C0.9800
C1—C61.4013 (17)C16—H160.9500
C1—C71.4870 (17)C17—H17A0.9800
C2—C31.3808 (18)C17—H17B0.9800
C2—H20.9500C17—H17C0.9800
C3—C41.3931 (17)C18—H18A0.9800
C3—H30.9500C18—H18B0.9800
C4—C51.3943 (17)C18—H18C0.9800
C5—C61.3850 (17)
C4—O1—H1O109.5O3—C10—C11117.60 (11)
C10—O3—H3O109.5O3—C10—C9122.04 (11)
C12—O4—C15117.61 (10)C11—C10—C9120.36 (11)
C7—N1—N2118.01 (10)C10—C11—C12119.89 (11)
C7—N1—H1N121.0C10—C11—H11120.1
N2—N1—H1N121.0C12—C11—H11120.1
C8—N2—N1117.12 (10)O4—C12—C11114.61 (11)
C16—N3—C17120.60 (13)O4—C12—C13124.26 (11)
C16—N3—C18121.12 (14)C11—C12—C13121.13 (11)
C17—N3—C18118.21 (14)C14—C13—C12118.28 (11)
C2—C1—C6118.28 (11)C14—C13—H13120.9
C2—C1—C7117.86 (11)C12—C13—H13120.9
C6—C1—C7123.83 (11)C13—C14—C9122.50 (11)
C3—C2—C1121.20 (11)C13—C14—H14118.7
C3—C2—H2119.4C9—C14—H14118.7
C1—C2—H2119.4O4—C15—H15A109.5
C2—C3—C4120.06 (12)O4—C15—H15B109.5
C2—C3—H3120.0H15A—C15—H15B109.5
C4—C3—H3120.0O4—C15—H15C109.5
O1—C4—C3122.10 (11)H15A—C15—H15C109.5
O1—C4—C5118.30 (11)H15B—C15—H15C109.5
C3—C4—C5119.60 (11)O5—C16—N3125.37 (13)
C6—C5—C4119.98 (11)O5—C16—H16117.3
C6—C5—H5120.0N3—C16—H16117.3
C4—C5—H5120.0N3—C17—H17A109.5
C5—C6—C1120.89 (11)N3—C17—H17B109.5
C5—C6—H6119.6H17A—C17—H17B109.5
C1—C6—H6119.6N3—C17—H17C109.5
O2—C7—N1121.23 (11)H17A—C17—H17C109.5
O2—C7—C1122.05 (11)H17B—C17—H17C109.5
N1—C7—C1116.72 (11)N3—C18—H18A109.5
N2—C8—C9119.62 (11)N3—C18—H18B109.5
N2—C8—H8120.2H18A—C18—H18B109.5
C9—C8—H8120.2N3—C18—H18C109.5
C14—C9—C10117.80 (11)H18A—C18—H18C109.5
C14—C9—C8119.86 (11)H18B—C18—H18C109.5
C10—C9—C8122.34 (11)
C7—N1—N2—C8178.29 (11)N2—C8—C9—C104.09 (18)
C6—C1—C2—C30.22 (19)C14—C9—C10—O3179.47 (11)
C7—C1—C2—C3177.82 (12)C8—C9—C10—O31.25 (19)
C1—C2—C3—C40.4 (2)C14—C9—C10—C110.74 (18)
C2—C3—C4—O1178.84 (12)C8—C9—C10—C11178.55 (11)
C2—C3—C4—C50.3 (2)O3—C10—C11—C12179.08 (11)
O1—C4—C5—C6179.11 (11)C9—C10—C11—C120.72 (19)
C3—C4—C5—C60.07 (19)C15—O4—C12—C11168.75 (11)
C4—C5—C6—C10.10 (19)C15—O4—C12—C1311.33 (17)
C2—C1—C6—C50.02 (19)C10—C11—C12—O4178.59 (11)
C7—C1—C6—C5177.94 (12)C10—C11—C12—C131.49 (19)
N2—N1—C7—O25.05 (18)O4—C12—C13—C14179.34 (11)
N2—N1—C7—C1175.38 (10)C11—C12—C13—C140.74 (19)
C2—C1—C7—O214.53 (18)C12—C13—C14—C90.79 (19)
C6—C1—C7—O2163.40 (12)C10—C9—C14—C131.52 (18)
C2—C1—C7—N1165.03 (11)C8—C9—C14—C13177.79 (12)
C6—C1—C7—N117.04 (18)C17—N3—C16—O51.2 (2)
N1—N2—C8—C9179.42 (11)C18—N3—C16—O5178.22 (15)
N2—C8—C9—C14175.18 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.822.656 (1)174
O3—H3o···N20.841.872.607 (1)145
N1—H1n···O50.881.952.787 (1)157
Symmetry code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC15H14N2O4·C3H7NO
Mr359.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)11.8273 (2), 7.8206 (2), 19.4218 (3)
β (°) 103.674 (1)
V3)1745.53 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11825, 4003, 3303
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.104, 1.01
No. of reflections4003
No. of parameters240
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.29, 0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.822.656 (1)174
O3—H3o···N20.841.872.607 (1)145
N1—H1n···O50.881.952.787 (1)157
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLair, N. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o189.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds