organic compounds
(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
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.
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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).
Supporting information
10.1107/S160053680804289X/bt2837sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680804289X/bt2837Isup2.hkl
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.
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).
Data collection: APEX2 (Bruker, 2007); cell
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).C15H14N2O4·C3H7NO | F(000) = 760 |
Mr = 359.38 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4180 reflections |
a = 11.8273 (2) Å | θ = 2.2–28.3° |
b = 7.8206 (2) Å | µ = 0.10 mm−1 |
c = 19.4218 (3) Å | T = 100 K |
β = 103.674 (1)° | Prism, colorless |
V = 1745.53 (6) Å3 | 0.30 × 0.25 × 0.15 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 3303 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω scans | h = −15→14 |
11825 measured reflections | k = −10→8 |
4003 independent reflections | l = −25→25 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C15H14N2O4·C3H7NO | V = 1745.53 (6) Å3 |
Mr = 359.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.8273 (2) Å | µ = 0.10 mm−1 |
b = 7.8206 (2) Å | T = 100 K |
c = 19.4218 (3) Å | 0.30 × 0.25 × 0.15 mm |
β = 103.674 (1)° |
Bruker SMART APEX diffractometer | 3303 reflections with I > 2σ(I) |
11825 measured reflections | Rint = 0.023 |
4003 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.29 e Å−3 |
4003 reflections | Δρmin = −0.22 e Å−3 |
240 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.66809 (8) | 0.74503 (12) | 0.66928 (5) | 0.0199 (2) | |
H1O | 0.6979 | 0.7676 | 0.7120 | 0.030* | |
O2 | 0.22303 (8) | 0.32357 (12) | 0.69867 (4) | 0.0211 (2) | |
O3 | −0.04810 (8) | 0.04690 (13) | 0.62396 (5) | 0.0228 (2) | |
H3O | 0.0069 | 0.1161 | 0.6259 | 0.034* | |
O4 | −0.40063 (8) | −0.13116 (12) | 0.47806 (5) | 0.0200 (2) | |
O5 | 0.18144 (8) | 0.46309 (12) | 0.44318 (5) | 0.0227 (2) | |
N1 | 0.17427 (9) | 0.37007 (14) | 0.58062 (5) | 0.0170 (2) | |
H1N | 0.1888 | 0.4217 | 0.5434 | 0.020* | |
N2 | 0.07635 (9) | 0.27015 (14) | 0.57472 (5) | 0.0173 (2) | |
N3 | 0.16184 (11) | 0.57465 (17) | 0.33359 (6) | 0.0285 (3) | |
C1 | 0.35639 (10) | 0.48355 (16) | 0.64886 (6) | 0.0154 (2) | |
C2 | 0.41943 (11) | 0.53743 (17) | 0.71534 (6) | 0.0188 (3) | |
H2 | 0.3901 | 0.5146 | 0.7559 | 0.023* | |
C3 | 0.52370 (11) | 0.62336 (17) | 0.72326 (7) | 0.0197 (3) | |
H3 | 0.5656 | 0.6584 | 0.7690 | 0.024* | |
C4 | 0.56747 (11) | 0.65871 (16) | 0.66420 (6) | 0.0164 (3) | |
C5 | 0.50566 (11) | 0.60607 (16) | 0.59728 (6) | 0.0179 (3) | |
H5 | 0.5351 | 0.6297 | 0.5568 | 0.022* | |
C6 | 0.40136 (11) | 0.51936 (16) | 0.58983 (6) | 0.0174 (3) | |
H6 | 0.3597 | 0.4837 | 0.5441 | 0.021* | |
C7 | 0.24710 (11) | 0.38628 (16) | 0.64518 (6) | 0.0162 (2) | |
C8 | 0.00648 (11) | 0.25971 (16) | 0.51315 (6) | 0.0170 (3) | |
H8 | 0.0228 | 0.3201 | 0.4742 | 0.020* | |
C9 | −0.09720 (10) | 0.15539 (16) | 0.50355 (6) | 0.0158 (2) | |
C10 | −0.12163 (11) | 0.05447 (16) | 0.55883 (6) | 0.0169 (3) | |
C11 | −0.22325 (11) | −0.04046 (16) | 0.54772 (6) | 0.0178 (3) | |
H11 | −0.2388 | −0.1090 | 0.5848 | 0.021* | |
C12 | −0.30237 (11) | −0.03528 (16) | 0.48223 (7) | 0.0169 (3) | |
C13 | −0.28026 (11) | 0.06116 (16) | 0.42650 (7) | 0.0183 (3) | |
H13 | −0.3341 | 0.0633 | 0.3817 | 0.022* | |
C14 | −0.17781 (11) | 0.15370 (16) | 0.43817 (6) | 0.0173 (3) | |
H14 | −0.1617 | 0.2186 | 0.4002 | 0.021* | |
C15 | −0.49470 (11) | −0.10776 (18) | 0.41743 (7) | 0.0208 (3) | |
H15A | −0.5643 | −0.1651 | 0.4252 | 0.031* | |
H15B | −0.4739 | −0.1568 | 0.3757 | 0.031* | |
H15C | −0.5105 | 0.0147 | 0.4098 | 0.031* | |
C16 | 0.21144 (11) | 0.56143 (17) | 0.40187 (7) | 0.0217 (3) | |
H16 | 0.2757 | 0.6343 | 0.4204 | 0.026* | |
C17 | 0.06495 (16) | 0.4656 (3) | 0.30112 (9) | 0.0449 (5) | |
H17A | 0.0502 | 0.3839 | 0.3362 | 0.067* | |
H17B | 0.0836 | 0.4033 | 0.2614 | 0.067* | |
H17C | −0.0045 | 0.5358 | 0.2837 | 0.067* | |
C18 | 0.20628 (17) | 0.6926 (3) | 0.28847 (10) | 0.0555 (6) | |
H18A | 0.2725 | 0.7558 | 0.3170 | 0.083* | |
H18B | 0.1448 | 0.7731 | 0.2665 | 0.083* | |
H18C | 0.2315 | 0.6283 | 0.2514 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0186 (4) | 0.0259 (5) | 0.0151 (4) | −0.0060 (4) | 0.0037 (3) | −0.0012 (4) |
O2 | 0.0185 (4) | 0.0274 (5) | 0.0168 (4) | −0.0028 (4) | 0.0030 (3) | 0.0036 (4) |
O3 | 0.0202 (5) | 0.0306 (6) | 0.0156 (4) | −0.0057 (4) | 0.0005 (4) | 0.0032 (4) |
O4 | 0.0167 (4) | 0.0236 (5) | 0.0188 (4) | −0.0051 (4) | 0.0026 (4) | 0.0005 (4) |
O5 | 0.0268 (5) | 0.0235 (5) | 0.0173 (4) | −0.0020 (4) | 0.0044 (4) | 0.0008 (4) |
N1 | 0.0158 (5) | 0.0190 (5) | 0.0155 (5) | −0.0034 (4) | 0.0023 (4) | 0.0013 (4) |
N2 | 0.0149 (5) | 0.0180 (5) | 0.0191 (5) | −0.0012 (4) | 0.0040 (4) | −0.0011 (4) |
N3 | 0.0272 (6) | 0.0369 (7) | 0.0224 (6) | 0.0071 (5) | 0.0079 (5) | 0.0088 (5) |
C1 | 0.0155 (6) | 0.0138 (6) | 0.0166 (6) | 0.0017 (5) | 0.0027 (5) | 0.0003 (4) |
C2 | 0.0213 (6) | 0.0210 (7) | 0.0146 (6) | −0.0028 (5) | 0.0054 (5) | −0.0002 (5) |
C3 | 0.0224 (6) | 0.0220 (7) | 0.0140 (6) | −0.0037 (5) | 0.0031 (5) | −0.0019 (5) |
C4 | 0.0156 (6) | 0.0152 (6) | 0.0180 (6) | 0.0003 (5) | 0.0033 (5) | 0.0004 (5) |
C5 | 0.0196 (6) | 0.0196 (6) | 0.0155 (6) | 0.0004 (5) | 0.0058 (5) | 0.0003 (5) |
C6 | 0.0183 (6) | 0.0188 (6) | 0.0138 (6) | 0.0009 (5) | 0.0013 (5) | −0.0008 (5) |
C7 | 0.0157 (6) | 0.0159 (6) | 0.0168 (6) | 0.0021 (5) | 0.0032 (5) | −0.0002 (5) |
C8 | 0.0178 (6) | 0.0168 (6) | 0.0168 (6) | 0.0008 (5) | 0.0050 (5) | 0.0004 (5) |
C9 | 0.0146 (6) | 0.0156 (6) | 0.0173 (6) | 0.0011 (5) | 0.0041 (5) | −0.0013 (5) |
C10 | 0.0167 (6) | 0.0190 (6) | 0.0145 (6) | 0.0024 (5) | 0.0028 (5) | −0.0008 (5) |
C11 | 0.0195 (6) | 0.0189 (6) | 0.0161 (6) | 0.0009 (5) | 0.0064 (5) | 0.0018 (5) |
C12 | 0.0151 (6) | 0.0160 (6) | 0.0203 (6) | −0.0003 (5) | 0.0055 (5) | −0.0027 (5) |
C13 | 0.0173 (6) | 0.0210 (7) | 0.0156 (6) | 0.0012 (5) | 0.0016 (5) | −0.0002 (5) |
C14 | 0.0189 (6) | 0.0179 (6) | 0.0151 (6) | 0.0012 (5) | 0.0042 (5) | 0.0022 (5) |
C15 | 0.0163 (6) | 0.0252 (7) | 0.0198 (6) | −0.0030 (5) | 0.0022 (5) | −0.0017 (5) |
C16 | 0.0197 (6) | 0.0211 (7) | 0.0239 (6) | 0.0011 (5) | 0.0045 (5) | 0.0008 (5) |
C17 | 0.0402 (10) | 0.0651 (13) | 0.0238 (8) | 0.0006 (9) | −0.0040 (7) | −0.0066 (8) |
C18 | 0.0496 (11) | 0.0763 (15) | 0.0460 (11) | 0.0161 (10) | 0.0217 (9) | 0.0405 (10) |
O1—C4 | 1.3514 (15) | C5—H5 | 0.9500 |
O1—H1O | 0.8400 | C6—H6 | 0.9500 |
O2—C7 | 1.2412 (15) | C8—C9 | 1.4478 (17) |
O3—C10 | 1.3565 (15) | C8—H8 | 0.9500 |
O3—H3O | 0.8400 | C9—C14 | 1.3962 (17) |
O4—C12 | 1.3693 (15) | C9—C10 | 1.4162 (17) |
O4—C15 | 1.4278 (15) | C10—C11 | 1.3855 (17) |
O5—C16 | 1.2229 (16) | C11—C12 | 1.3901 (17) |
N1—C7 | 1.3489 (15) | C11—H11 | 0.9500 |
N1—N2 | 1.3791 (14) | C12—C13 | 1.3938 (17) |
N1—H1N | 0.8800 | C13—C14 | 1.3832 (17) |
N2—C8 | 1.2855 (16) | C13—H13 | 0.9500 |
N3—C16 | 1.3212 (17) | C14—H14 | 0.9500 |
N3—C17 | 1.448 (2) | C15—H15A | 0.9800 |
N3—C18 | 1.454 (2) | C15—H15B | 0.9800 |
C1—C2 | 1.3948 (17) | C15—H15C | 0.9800 |
C1—C6 | 1.4013 (17) | C16—H16 | 0.9500 |
C1—C7 | 1.4870 (17) | C17—H17A | 0.9800 |
C2—C3 | 1.3808 (18) | C17—H17B | 0.9800 |
C2—H2 | 0.9500 | C17—H17C | 0.9800 |
C3—C4 | 1.3931 (17) | C18—H18A | 0.9800 |
C3—H3 | 0.9500 | C18—H18B | 0.9800 |
C4—C5 | 1.3943 (17) | C18—H18C | 0.9800 |
C5—C6 | 1.3850 (17) | ||
C4—O1—H1O | 109.5 | O3—C10—C11 | 117.60 (11) |
C10—O3—H3O | 109.5 | O3—C10—C9 | 122.04 (11) |
C12—O4—C15 | 117.61 (10) | C11—C10—C9 | 120.36 (11) |
C7—N1—N2 | 118.01 (10) | C10—C11—C12 | 119.89 (11) |
C7—N1—H1N | 121.0 | C10—C11—H11 | 120.1 |
N2—N1—H1N | 121.0 | C12—C11—H11 | 120.1 |
C8—N2—N1 | 117.12 (10) | O4—C12—C11 | 114.61 (11) |
C16—N3—C17 | 120.60 (13) | O4—C12—C13 | 124.26 (11) |
C16—N3—C18 | 121.12 (14) | C11—C12—C13 | 121.13 (11) |
C17—N3—C18 | 118.21 (14) | C14—C13—C12 | 118.28 (11) |
C2—C1—C6 | 118.28 (11) | C14—C13—H13 | 120.9 |
C2—C1—C7 | 117.86 (11) | C12—C13—H13 | 120.9 |
C6—C1—C7 | 123.83 (11) | C13—C14—C9 | 122.50 (11) |
C3—C2—C1 | 121.20 (11) | C13—C14—H14 | 118.7 |
C3—C2—H2 | 119.4 | C9—C14—H14 | 118.7 |
C1—C2—H2 | 119.4 | O4—C15—H15A | 109.5 |
C2—C3—C4 | 120.06 (12) | O4—C15—H15B | 109.5 |
C2—C3—H3 | 120.0 | H15A—C15—H15B | 109.5 |
C4—C3—H3 | 120.0 | O4—C15—H15C | 109.5 |
O1—C4—C3 | 122.10 (11) | H15A—C15—H15C | 109.5 |
O1—C4—C5 | 118.30 (11) | H15B—C15—H15C | 109.5 |
C3—C4—C5 | 119.60 (11) | O5—C16—N3 | 125.37 (13) |
C6—C5—C4 | 119.98 (11) | O5—C16—H16 | 117.3 |
C6—C5—H5 | 120.0 | N3—C16—H16 | 117.3 |
C4—C5—H5 | 120.0 | N3—C17—H17A | 109.5 |
C5—C6—C1 | 120.89 (11) | N3—C17—H17B | 109.5 |
C5—C6—H6 | 119.6 | H17A—C17—H17B | 109.5 |
C1—C6—H6 | 119.6 | N3—C17—H17C | 109.5 |
O2—C7—N1 | 121.23 (11) | H17A—C17—H17C | 109.5 |
O2—C7—C1 | 122.05 (11) | H17B—C17—H17C | 109.5 |
N1—C7—C1 | 116.72 (11) | N3—C18—H18A | 109.5 |
N2—C8—C9 | 119.62 (11) | N3—C18—H18B | 109.5 |
N2—C8—H8 | 120.2 | H18A—C18—H18B | 109.5 |
C9—C8—H8 | 120.2 | N3—C18—H18C | 109.5 |
C14—C9—C10 | 117.80 (11) | H18A—C18—H18C | 109.5 |
C14—C9—C8 | 119.86 (11) | H18B—C18—H18C | 109.5 |
C10—C9—C8 | 122.34 (11) | ||
C7—N1—N2—C8 | 178.29 (11) | N2—C8—C9—C10 | −4.09 (18) |
C6—C1—C2—C3 | −0.22 (19) | C14—C9—C10—O3 | 179.47 (11) |
C7—C1—C2—C3 | 177.82 (12) | C8—C9—C10—O3 | −1.25 (19) |
C1—C2—C3—C4 | 0.4 (2) | C14—C9—C10—C11 | −0.74 (18) |
C2—C3—C4—O1 | 178.84 (12) | C8—C9—C10—C11 | 178.55 (11) |
C2—C3—C4—C5 | −0.3 (2) | O3—C10—C11—C12 | 179.08 (11) |
O1—C4—C5—C6 | −179.11 (11) | C9—C10—C11—C12 | −0.72 (19) |
C3—C4—C5—C6 | 0.07 (19) | C15—O4—C12—C11 | 168.75 (11) |
C4—C5—C6—C1 | 0.10 (19) | C15—O4—C12—C13 | −11.33 (17) |
C2—C1—C6—C5 | −0.02 (19) | C10—C11—C12—O4 | −178.59 (11) |
C7—C1—C6—C5 | −177.94 (12) | C10—C11—C12—C13 | 1.49 (19) |
N2—N1—C7—O2 | −5.05 (18) | O4—C12—C13—C14 | 179.34 (11) |
N2—N1—C7—C1 | 175.38 (10) | C11—C12—C13—C14 | −0.74 (19) |
C2—C1—C7—O2 | −14.53 (18) | C12—C13—C14—C9 | −0.79 (19) |
C6—C1—C7—O2 | 163.40 (12) | C10—C9—C14—C13 | 1.52 (18) |
C2—C1—C7—N1 | 165.03 (11) | C8—C9—C14—C13 | −177.79 (12) |
C6—C1—C7—N1 | −17.04 (18) | C17—N3—C16—O5 | −1.2 (2) |
N1—N2—C8—C9 | 179.42 (11) | C18—N3—C16—O5 | −178.22 (15) |
N2—C8—C9—C14 | 175.18 (12) |
D—H···A | D—H | H···A | D···A | 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+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O4·C3H7NO |
Mr | 359.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.8273 (2), 7.8206 (2), 19.4218 (3) |
β (°) | 103.674 (1) |
V (Å3) | 1745.53 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11825, 4003, 3303 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.104, 1.01 |
No. of reflections | 4003 |
No. of parameters | 240 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | 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+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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lair, N. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
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