Related literature
For the corresponding monohydrate, see: Lair et al. (2009
).
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
|
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) . | |
Data collection: APEX2 (Bruker, 2007
); cell refinement: 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
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 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).
(
E)-4-Hydroxy-
N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide
N,
N-dimethylformamide solvate
top Crystal data top 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 | |
Data collection top 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 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)] = 0.038 | 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 |
Crystal data top 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)° | |
Data collection top Bruker SMART APEX diffractometer | 3303 reflections with I > 2σ(I) |
11825 measured reflections | Rint = 0.023 |
4003 independent reflections | |
Refinement top 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 | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top 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) | | |
Hydrogen-bond geometry (Å, º) top 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 |
Hydrogen-bond geometry (Å, º) top 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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