





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807065038/ci2538sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807065038/ci2538Isup2.hkl |
CCDC reference: 674523
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.055
- wR factor = 0.144
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Salicylaldehyde (1.0 mmol, 122.1 mg) and 3,4-dihydroxybenzoic acid hydrazide (1.0 mmol, 168.2 mg) were dissolved in a methanol solution (70 ml). The mixture was stirred at room temperature for 1 h and filtered. After keeping the filtrate in air for a week, yellow block-shaped crystals were formed.
H atoms of the water molecules and –NH groups were located in a difference Fourier map and refined isotropically, with N—H, O—H and H···H (in water) distances restrained to 0.90 (1) Å, 0.85 (1) Å and 1.37 (2) Å, respectively, and with a fixed Uiso value of 0.08 Å2. The remaining H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O, Cmethyl).
Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the structure of Schiff base compounds (Diao, 2007; Diao et al., 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.
The asymmetric unit of the title compound consists of two Schiff base molecules, three water molecules and one methanol molecule (Fig. 1). The corresponding bond lengths and angles in the two Schiff base molecules are nearly identical. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 7.8 (2)° and that between the C15—C20 and C23—C28 benzene rings is 4.0 (2)°. The structure of each molecule is stabilized by O—H···O and O—H···N intramolecular hydrogen bonds.
In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).
For the biological properties of Schiff base compounds, see: Brückner et al. (2000); Harrop et al. (2003); Ren et al. (2002). For related structures, see: Diao (2007); Diao et al. (2007); Huang et al. (2007); Li et al. (2007).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
![]() | Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
![]() | Fig. 2. Part of the crystal packing of the title compound. |
C14H12N2O4·0.5CH4O·1.5H2O | Z = 4 |
Mr = 315.30 | F(000) = 664 |
Triclinic, P1 | Dx = 1.376 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.707 (2) Å | Cell parameters from 1027 reflections |
b = 11.994 (2) Å | θ = 2.6–24.4° |
c = 14.103 (3) Å | µ = 0.11 mm−1 |
α = 111.56 (3)° | T = 298 K |
β = 103.13 (3)° | Block, yellow |
γ = 104.72 (3)° | 0.17 × 0.15 × 0.15 mm |
V = 1522.2 (8) Å3 |
Bruker SMART CCD area-detector diffractometer | 6429 independent reflections |
Radiation source: fine-focus sealed tube | 2812 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω scans | θmax = 26.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→9 |
Tmin = 0.982, Tmax = 0.984 | k = −14→15 |
9348 measured reflections | l = −14→17 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3 |
6429 reflections | (Δ/σ)max = 0.001 |
438 parameters | Δρmax = 0.17 e Å−3 |
11 restraints | Δρmin = −0.21 e Å−3 |
C14H12N2O4·0.5CH4O·1.5H2O | γ = 104.72 (3)° |
Mr = 315.30 | V = 1522.2 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.707 (2) Å | Mo Kα radiation |
b = 11.994 (2) Å | µ = 0.11 mm−1 |
c = 14.103 (3) Å | T = 298 K |
α = 111.56 (3)° | 0.17 × 0.15 × 0.15 mm |
β = 103.13 (3)° |
Bruker SMART CCD area-detector diffractometer | 6429 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2812 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.984 | Rint = 0.030 |
9348 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 11 restraints |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.17 e Å−3 |
6429 reflections | Δρmin = −0.21 e Å−3 |
438 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.7795 (2) | 0.64000 (17) | 1.35513 (13) | 0.0587 (6) | |
H1 | 0.7625 | 0.5633 | 1.3388 | 0.088* | |
O2 | 0.7267 (2) | 0.85547 (16) | 1.37077 (14) | 0.0528 (5) | |
H2 | 0.7490 | 0.8323 | 1.4179 | 0.079* | |
O3 | 0.7116 (2) | 0.39011 (18) | 0.96456 (14) | 0.0609 (6) | |
O4 | 0.6696 (2) | 0.19447 (18) | 0.67631 (15) | 0.0605 (6) | |
H4 | 0.6723 | 0.2551 | 0.7296 | 0.091* | |
O5 | 0.6555 (2) | 0.13711 (18) | −0.10815 (14) | 0.0675 (6) | |
H5 | 0.6701 | 0.2132 | −0.0932 | 0.101* | |
O6 | 0.7472 (2) | −0.05612 (18) | −0.11851 (15) | 0.0635 (6) | |
H6 | 0.7496 | −0.0212 | −0.1586 | 0.095* | |
O7 | 0.71818 (18) | 0.38404 (17) | 0.28249 (13) | 0.0490 (5) | |
O8 | 0.7971 (2) | 0.60616 (18) | 0.57457 (15) | 0.0625 (6) | |
H8 | 0.7958 | 0.5464 | 0.5214 | 0.094* | |
O9 | 0.8032 (2) | 0.04122 (18) | 0.73419 (16) | 0.0581 (5) | |
H9 | 0.7470 | 0.0701 | 0.7128 | 0.087* | |
O10 | 0.5614 (2) | 0.6868 (2) | 0.83236 (18) | 0.0619 (6) | |
O11 | 0.8239 (2) | 0.84887 (19) | 0.56226 (15) | 0.0563 (6) | |
O12 | 0.9056 (2) | 0.11266 (19) | 0.42584 (19) | 0.0669 (6) | |
N1 | 0.6301 (2) | 0.4906 (2) | 0.87321 (17) | 0.0401 (5) | |
N2 | 0.6220 (2) | 0.3958 (2) | 0.77792 (17) | 0.0406 (5) | |
N3 | 0.8292 (2) | 0.30112 (19) | 0.37667 (17) | 0.0396 (5) | |
N4 | 0.8380 (2) | 0.39822 (19) | 0.47159 (16) | 0.0382 (5) | |
C1 | 0.6883 (2) | 0.5837 (2) | 1.06912 (19) | 0.0370 (6) | |
C2 | 0.7299 (2) | 0.5671 (2) | 1.16190 (19) | 0.0425 (7) | |
H2A | 0.7506 | 0.4945 | 1.1559 | 0.051* | |
C3 | 0.7415 (3) | 0.6543 (2) | 1.2623 (2) | 0.0404 (6) | |
C4 | 0.7141 (3) | 0.7644 (2) | 1.2724 (2) | 0.0401 (6) | |
C5 | 0.6716 (3) | 0.7821 (2) | 1.1813 (2) | 0.0461 (7) | |
H5A | 0.6512 | 0.8549 | 1.1877 | 0.055* | |
C6 | 0.6588 (3) | 0.6929 (2) | 1.0802 (2) | 0.0464 (7) | |
H6A | 0.6303 | 0.7063 | 1.0192 | 0.056* | |
C7 | 0.6776 (3) | 0.4813 (3) | 0.9654 (2) | 0.0418 (7) | |
C8 | 0.5749 (2) | 0.4005 (3) | 0.6887 (2) | 0.0431 (7) | |
H8A | 0.5451 | 0.4669 | 0.6888 | 0.052* | |
C9 | 0.5675 (2) | 0.3036 (3) | 0.58771 (19) | 0.0399 (6) | |
C10 | 0.6148 (3) | 0.2049 (3) | 0.5842 (2) | 0.0457 (7) | |
C11 | 0.6070 (3) | 0.1131 (3) | 0.4859 (2) | 0.0602 (9) | |
H11 | 0.6400 | 0.0481 | 0.4845 | 0.072* | |
C12 | 0.5506 (3) | 0.1181 (3) | 0.3907 (3) | 0.0722 (11) | |
H12 | 0.5436 | 0.0554 | 0.3245 | 0.087* | |
C13 | 0.5047 (3) | 0.2150 (4) | 0.3926 (2) | 0.0697 (10) | |
H13 | 0.4679 | 0.2187 | 0.3280 | 0.084* | |
C14 | 0.5126 (3) | 0.3074 (3) | 0.4900 (2) | 0.0555 (8) | |
H14 | 0.4809 | 0.3729 | 0.4904 | 0.067* | |
C15 | 0.7553 (3) | 0.1977 (2) | 0.17858 (19) | 0.0389 (6) | |
C16 | 0.7038 (3) | 0.2094 (2) | 0.0849 (2) | 0.0447 (7) | |
H16 | 0.6703 | 0.2747 | 0.0890 | 0.054* | |
C17 | 0.7011 (3) | 0.1264 (3) | −0.0143 (2) | 0.0475 (7) | |
C18 | 0.7470 (3) | 0.0272 (2) | −0.0213 (2) | 0.0481 (7) | |
C19 | 0.7935 (3) | 0.0113 (3) | 0.0699 (2) | 0.0581 (8) | |
H19 | 0.8221 | −0.0571 | 0.0645 | 0.070* | |
C20 | 0.7984 (3) | 0.0957 (2) | 0.1699 (2) | 0.0517 (8) | |
H20 | 0.8306 | 0.0843 | 0.2314 | 0.062* | |
C21 | 0.7657 (3) | 0.3000 (2) | 0.2826 (2) | 0.0385 (6) | |
C22 | 0.8895 (2) | 0.3959 (2) | 0.5612 (2) | 0.0406 (6) | |
H22 | 0.9212 | 0.3306 | 0.5616 | 0.049* | |
C23 | 0.8987 (2) | 0.4949 (2) | 0.6626 (2) | 0.0404 (7) | |
C24 | 0.8529 (3) | 0.5961 (3) | 0.6665 (2) | 0.0462 (7) | |
C25 | 0.8627 (3) | 0.6882 (3) | 0.7647 (2) | 0.0606 (8) | |
H25 | 0.8320 | 0.7546 | 0.7667 | 0.073* | |
C26 | 0.9175 (3) | 0.6818 (3) | 0.8592 (3) | 0.0686 (10) | |
H26 | 0.9241 | 0.7445 | 0.9252 | 0.082* | |
C27 | 0.9630 (3) | 0.5839 (3) | 0.8583 (2) | 0.0653 (9) | |
H27 | 0.9999 | 0.5801 | 0.9229 | 0.078* | |
C28 | 0.9532 (3) | 0.4917 (3) | 0.7604 (2) | 0.0518 (8) | |
H28 | 0.9839 | 0.4256 | 0.7596 | 0.062* | |
C29 | 0.9365 (3) | 0.1399 (4) | 0.7883 (3) | 0.1063 (14) | |
H29A | 0.9356 | 0.2106 | 0.8488 | 0.159* | |
H29B | 0.9623 | 0.1696 | 0.7384 | 0.159* | |
H29C | 1.0019 | 0.1066 | 0.8145 | 0.159* | |
H3 | 0.857 (3) | 0.238 (2) | 0.382 (2) | 0.080* | |
H11B | 0.799 (3) | 0.897 (2) | 0.6091 (19) | 0.080* | |
H12B | 0.852 (2) | 0.0381 (15) | 0.411 (2) | 0.080* | |
H1A | 0.608 (3) | 0.5579 (19) | 0.871 (2) | 0.080* | |
H12A | 0.9848 (14) | 0.110 (3) | 0.428 (2) | 0.080* | |
H11A | 0.806 (3) | 0.7774 (15) | 0.565 (2) | 0.080* | |
H10A | 0.613 (2) | 0.7585 (17) | 0.840 (2) | 0.080* | |
H10B | 0.4781 (12) | 0.677 (3) | 0.804 (2) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0975 (16) | 0.0432 (11) | 0.0340 (11) | 0.0319 (12) | 0.0162 (10) | 0.0165 (9) |
O2 | 0.0792 (14) | 0.0403 (11) | 0.0418 (11) | 0.0273 (10) | 0.0260 (11) | 0.0157 (9) |
O3 | 0.1012 (16) | 0.0528 (13) | 0.0427 (12) | 0.0477 (12) | 0.0267 (11) | 0.0225 (10) |
O4 | 0.0862 (15) | 0.0518 (13) | 0.0495 (13) | 0.0376 (12) | 0.0249 (12) | 0.0205 (11) |
O5 | 0.1172 (18) | 0.0582 (13) | 0.0381 (12) | 0.0494 (14) | 0.0273 (11) | 0.0220 (10) |
O6 | 0.1113 (17) | 0.0439 (12) | 0.0450 (12) | 0.0406 (12) | 0.0357 (12) | 0.0174 (10) |
O7 | 0.0684 (13) | 0.0426 (11) | 0.0432 (11) | 0.0319 (10) | 0.0213 (9) | 0.0185 (9) |
O8 | 0.0940 (16) | 0.0526 (13) | 0.0508 (13) | 0.0424 (12) | 0.0278 (12) | 0.0222 (11) |
O9 | 0.0649 (14) | 0.0559 (13) | 0.0523 (13) | 0.0294 (11) | 0.0210 (11) | 0.0185 (10) |
O10 | 0.0650 (14) | 0.0575 (14) | 0.0714 (15) | 0.0288 (12) | 0.0174 (13) | 0.0375 (13) |
O11 | 0.0738 (14) | 0.0496 (13) | 0.0485 (13) | 0.0278 (12) | 0.0303 (10) | 0.0168 (11) |
O12 | 0.0593 (14) | 0.0522 (13) | 0.0956 (16) | 0.0269 (12) | 0.0253 (14) | 0.0371 (13) |
N1 | 0.0532 (14) | 0.0373 (13) | 0.0330 (13) | 0.0209 (11) | 0.0183 (11) | 0.0146 (11) |
N2 | 0.0461 (14) | 0.0429 (13) | 0.0334 (13) | 0.0182 (11) | 0.0158 (10) | 0.0157 (11) |
N3 | 0.0494 (14) | 0.0353 (13) | 0.0382 (13) | 0.0191 (11) | 0.0202 (11) | 0.0157 (11) |
N4 | 0.0444 (13) | 0.0343 (12) | 0.0326 (13) | 0.0145 (10) | 0.0158 (10) | 0.0107 (10) |
C1 | 0.0433 (16) | 0.0346 (15) | 0.0330 (15) | 0.0160 (12) | 0.0144 (12) | 0.0139 (12) |
C2 | 0.0541 (17) | 0.0385 (15) | 0.0367 (16) | 0.0246 (14) | 0.0139 (13) | 0.0155 (13) |
C3 | 0.0493 (17) | 0.0365 (16) | 0.0343 (15) | 0.0152 (13) | 0.0132 (13) | 0.0164 (13) |
C4 | 0.0484 (17) | 0.0315 (15) | 0.0395 (16) | 0.0143 (13) | 0.0195 (13) | 0.0133 (13) |
C5 | 0.0668 (19) | 0.0341 (16) | 0.0479 (17) | 0.0263 (14) | 0.0255 (15) | 0.0213 (14) |
C6 | 0.0663 (19) | 0.0428 (17) | 0.0372 (16) | 0.0245 (15) | 0.0196 (14) | 0.0218 (14) |
C7 | 0.0511 (17) | 0.0421 (17) | 0.0423 (17) | 0.0221 (14) | 0.0210 (13) | 0.0236 (14) |
C8 | 0.0419 (16) | 0.0460 (17) | 0.0465 (17) | 0.0165 (13) | 0.0189 (13) | 0.0240 (15) |
C9 | 0.0363 (15) | 0.0448 (17) | 0.0320 (15) | 0.0082 (13) | 0.0118 (12) | 0.0154 (13) |
C10 | 0.0476 (17) | 0.0429 (17) | 0.0414 (17) | 0.0103 (14) | 0.0208 (14) | 0.0150 (14) |
C11 | 0.066 (2) | 0.0478 (19) | 0.059 (2) | 0.0121 (16) | 0.0345 (17) | 0.0141 (16) |
C12 | 0.074 (2) | 0.060 (2) | 0.043 (2) | −0.0081 (19) | 0.0279 (18) | 0.0009 (18) |
C13 | 0.063 (2) | 0.083 (3) | 0.0344 (19) | −0.005 (2) | 0.0102 (15) | 0.0223 (19) |
C14 | 0.0486 (18) | 0.067 (2) | 0.0442 (18) | 0.0118 (16) | 0.0135 (15) | 0.0269 (17) |
C15 | 0.0498 (16) | 0.0331 (15) | 0.0353 (15) | 0.0158 (13) | 0.0191 (13) | 0.0144 (13) |
C16 | 0.0624 (19) | 0.0397 (16) | 0.0397 (16) | 0.0274 (14) | 0.0214 (14) | 0.0182 (14) |
C17 | 0.066 (2) | 0.0400 (17) | 0.0391 (17) | 0.0231 (15) | 0.0198 (15) | 0.0183 (14) |
C18 | 0.072 (2) | 0.0326 (16) | 0.0368 (16) | 0.0193 (15) | 0.0221 (14) | 0.0108 (13) |
C19 | 0.094 (2) | 0.0401 (17) | 0.0498 (19) | 0.0364 (17) | 0.0301 (17) | 0.0202 (15) |
C20 | 0.082 (2) | 0.0402 (17) | 0.0418 (17) | 0.0300 (16) | 0.0247 (15) | 0.0211 (14) |
C21 | 0.0483 (17) | 0.0343 (15) | 0.0379 (16) | 0.0162 (13) | 0.0199 (13) | 0.0181 (13) |
C22 | 0.0368 (15) | 0.0391 (16) | 0.0443 (17) | 0.0139 (13) | 0.0146 (13) | 0.0172 (14) |
C23 | 0.0358 (15) | 0.0408 (16) | 0.0365 (16) | 0.0082 (13) | 0.0110 (12) | 0.0143 (13) |
C24 | 0.0454 (17) | 0.0419 (17) | 0.0424 (17) | 0.0091 (14) | 0.0170 (13) | 0.0139 (14) |
C25 | 0.068 (2) | 0.0479 (19) | 0.052 (2) | 0.0184 (16) | 0.0275 (17) | 0.0067 (16) |
C26 | 0.064 (2) | 0.064 (2) | 0.043 (2) | 0.0083 (19) | 0.0207 (17) | −0.0015 (17) |
C27 | 0.056 (2) | 0.082 (3) | 0.0359 (18) | 0.0100 (19) | 0.0089 (15) | 0.0192 (18) |
C28 | 0.0489 (18) | 0.0583 (19) | 0.0454 (18) | 0.0160 (15) | 0.0149 (14) | 0.0245 (16) |
C29 | 0.066 (3) | 0.096 (3) | 0.126 (3) | 0.015 (2) | 0.010 (2) | 0.043 (3) |
O1—C3 | 1.367 (3) | C6—H6A | 0.93 |
O1—H1 | 0.82 | C8—C9 | 1.440 (3) |
O2—C4 | 1.365 (3) | C8—H8A | 0.93 |
O2—H2 | 0.82 | C9—C10 | 1.390 (4) |
O3—C7 | 1.234 (3) | C9—C14 | 1.392 (3) |
O4—C10 | 1.363 (3) | C10—C11 | 1.386 (4) |
O4—H4 | 0.82 | C11—C12 | 1.372 (4) |
O5—C17 | 1.368 (3) | C11—H11 | 0.93 |
O5—H5 | 0.82 | C12—C13 | 1.365 (4) |
O6—C18 | 1.368 (3) | C12—H12 | 0.93 |
O6—H6 | 0.82 | C13—C14 | 1.380 (4) |
O7—C21 | 1.240 (3) | C13—H13 | 0.93 |
O8—C24 | 1.361 (3) | C14—H14 | 0.93 |
O8—H8 | 0.82 | C15—C16 | 1.384 (3) |
O9—C29 | 1.416 (3) | C15—C20 | 1.388 (3) |
O9—H9 | 0.82 | C15—C21 | 1.484 (3) |
O10—H10A | 0.846 (10) | C16—C17 | 1.375 (3) |
O10—H10B | 0.85 (2) | C16—H16 | 0.93 |
O11—H11B | 0.85 (3) | C17—C18 | 1.378 (4) |
O11—H11A | 0.85 (2) | C18—C19 | 1.370 (4) |
O12—H12B | 0.85 (2) | C19—C20 | 1.381 (4) |
O12—H12A | 0.85 (2) | C19—H19 | 0.93 |
N1—C7 | 1.341 (3) | C20—H20 | 0.93 |
N1—N2 | 1.372 (3) | C22—C23 | 1.447 (3) |
N1—H1A | 0.91 (3) | C22—H22 | 0.93 |
N2—C8 | 1.272 (3) | C23—C28 | 1.388 (3) |
N3—C21 | 1.340 (3) | C23—C24 | 1.407 (4) |
N3—N4 | 1.378 (3) | C24—C25 | 1.379 (4) |
N3—H3 | 0.90 (3) | C25—C26 | 1.367 (4) |
N4—C22 | 1.273 (3) | C25—H25 | 0.93 |
C1—C6 | 1.387 (3) | C26—C27 | 1.379 (4) |
C1—C2 | 1.387 (3) | C26—H26 | 0.93 |
C1—C7 | 1.481 (3) | C27—C28 | 1.376 (4) |
C2—C3 | 1.372 (3) | C27—H27 | 0.93 |
C2—H2A | 0.93 | C28—H28 | 0.93 |
C3—C4 | 1.388 (3) | C29—H29A | 0.96 |
C4—C5 | 1.373 (3) | C29—H29B | 0.96 |
C5—C6 | 1.383 (3) | C29—H29C | 0.96 |
C5—H5A | 0.93 | ||
C3—O1—H1 | 109.5 | C12—C13—C14 | 120.4 (3) |
C4—O2—H2 | 109.5 | C12—C13—H13 | 119.8 |
C10—O4—H4 | 109.5 | C14—C13—H13 | 119.8 |
C17—O5—H5 | 109.5 | C13—C14—C9 | 120.6 (3) |
C18—O6—H6 | 109.5 | C13—C14—H14 | 119.7 |
C24—O8—H8 | 109.5 | C9—C14—H14 | 119.7 |
C29—O9—H9 | 109.5 | C16—C15—C20 | 118.5 (2) |
H10A—O10—H10B | 108 (2) | C16—C15—C21 | 116.7 (2) |
H11B—O11—H11A | 107 (2) | C20—C15—C21 | 124.7 (2) |
H12B—O12—H12A | 108 (2) | C17—C16—C15 | 121.4 (3) |
C7—N1—N2 | 117.5 (2) | C17—C16—H16 | 119.3 |
C7—N1—H1A | 123.7 (19) | C15—C16—H16 | 119.3 |
N2—N1—H1A | 118.7 (19) | O5—C17—C16 | 123.3 (3) |
C8—N2—N1 | 119.1 (2) | O5—C17—C18 | 117.2 (2) |
C21—N3—N4 | 117.2 (2) | C16—C17—C18 | 119.5 (3) |
C21—N3—H3 | 124.4 (19) | O6—C18—C19 | 119.2 (3) |
N4—N3—H3 | 118.0 (18) | O6—C18—C17 | 120.9 (2) |
C22—N4—N3 | 118.1 (2) | C19—C18—C17 | 119.9 (3) |
C6—C1—C2 | 118.0 (2) | C18—C19—C20 | 120.8 (3) |
C6—C1—C7 | 125.4 (2) | C18—C19—H19 | 119.6 |
C2—C1—C7 | 116.6 (2) | C20—C19—H19 | 119.6 |
C3—C2—C1 | 122.0 (3) | C19—C20—C15 | 119.9 (3) |
C3—C2—H2A | 119.0 | C19—C20—H20 | 120.0 |
C1—C2—H2A | 119.0 | C15—C20—H20 | 120.0 |
O1—C3—C2 | 123.7 (2) | O7—C21—N3 | 120.5 (2) |
O1—C3—C4 | 117.0 (2) | O7—C21—C15 | 120.6 (2) |
C2—C3—C4 | 119.3 (2) | N3—C21—C15 | 118.9 (2) |
O2—C4—C5 | 118.8 (2) | N4—C22—C23 | 119.9 (3) |
O2—C4—C3 | 121.6 (2) | N4—C22—H22 | 120.1 |
C5—C4—C3 | 119.6 (2) | C23—C22—H22 | 120.1 |
C4—C5—C6 | 120.7 (3) | C28—C23—C24 | 117.7 (3) |
C4—C5—H5A | 119.7 | C28—C23—C22 | 120.0 (3) |
C6—C5—H5A | 119.7 | C24—C23—C22 | 122.3 (2) |
C5—C6—C1 | 120.4 (2) | O8—C24—C25 | 117.9 (3) |
C5—C6—H6A | 119.8 | O8—C24—C23 | 121.7 (2) |
C1—C6—H6A | 119.8 | C25—C24—C23 | 120.4 (3) |
O3—C7—N1 | 121.3 (2) | C26—C25—C24 | 120.0 (3) |
O3—C7—C1 | 120.6 (2) | C26—C25—H25 | 120.0 |
N1—C7—C1 | 118.1 (2) | C24—C25—H25 | 120.0 |
N2—C8—C9 | 120.3 (3) | C25—C26—C27 | 121.0 (3) |
N2—C8—H8A | 119.8 | C25—C26—H26 | 119.5 |
C9—C8—H8A | 119.8 | C27—C26—H26 | 119.5 |
C10—C9—C14 | 118.2 (3) | C28—C27—C26 | 119.1 (3) |
C10—C9—C8 | 121.8 (2) | C28—C27—H27 | 120.4 |
C14—C9—C8 | 120.0 (3) | C26—C27—H27 | 120.4 |
O4—C10—C11 | 117.7 (3) | C27—C28—C23 | 121.7 (3) |
O4—C10—C9 | 121.7 (2) | C27—C28—H28 | 119.2 |
C11—C10—C9 | 120.6 (3) | C23—C28—H28 | 119.2 |
C12—C11—C10 | 120.0 (3) | O9—C29—H29A | 109.5 |
C12—C11—H11 | 120.0 | O9—C29—H29B | 109.5 |
C10—C11—H11 | 120.0 | H29A—C29—H29B | 109.5 |
C13—C12—C11 | 120.2 (3) | O9—C29—H29C | 109.5 |
C13—C12—H12 | 119.9 | H29A—C29—H29C | 109.5 |
C11—C12—H12 | 119.9 | H29B—C29—H29C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10B···O7i | 0.85 (2) | 1.96 (1) | 2.793 (3) | 168 (3) |
O10—H10A···O6ii | 0.85 (1) | 2.10 (1) | 2.938 (3) | 173 (3) |
O11—H11A···O8 | 0.85 (2) | 2.09 (1) | 2.925 (3) | 170 (3) |
O12—H12A···O11iii | 0.85 (2) | 1.94 (1) | 2.770 (3) | 165 (3) |
N1—H1A···O10 | 0.91 (3) | 1.96 (3) | 2.844 (3) | 167 (3) |
O12—H12B···O2iv | 0.85 (2) | 2.04 (1) | 2.889 (3) | 177 (3) |
O11—H11B···O9v | 0.85 (3) | 1.95 (3) | 2.765 (3) | 162 (3) |
N3—H3···O12 | 0.90 (3) | 1.96 (3) | 2.845 (3) | 165 (3) |
O8—H8···N4 | 0.82 | 1.87 | 2.589 (3) | 146 |
O6—H6···O9vi | 0.82 | 2.04 | 2.834 (3) | 161 |
O5—H5···O3vi | 0.82 | 1.86 | 2.670 (3) | 170 |
O4—H4···N2 | 0.82 | 1.84 | 2.561 (3) | 146 |
O2—H2···O1 | 0.82 | 2.29 | 2.725 (3) | 114 |
O2—H2···O11vii | 0.82 | 1.93 | 2.703 (3) | 158 |
O1—H1···O7vii | 0.82 | 1.88 | 2.695 (3) | 172 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z+1; (iii) −x+2, −y+1, −z+1; (iv) x, y−1, z−1; (v) x, y+1, z; (vi) x, y, z−1; (vii) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H12N2O4·0.5CH4O·1.5H2O |
Mr | 315.30 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.707 (2), 11.994 (2), 14.103 (3) |
α, β, γ (°) | 111.56 (3), 103.13 (3), 104.72 (3) |
V (Å3) | 1522.2 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.17 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.982, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9348, 6429, 2812 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.637 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.144, 0.97 |
No. of reflections | 6429 |
No. of parameters | 438 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10B···O7i | 0.85 (2) | 1.96 (1) | 2.793 (3) | 168 (3) |
O10—H10A···O6ii | 0.85 (1) | 2.10 (1) | 2.938 (3) | 173 (3) |
O11—H11A···O8 | 0.85 (2) | 2.09 (1) | 2.925 (3) | 170 (3) |
O12—H12A···O11iii | 0.85 (2) | 1.94 (1) | 2.770 (3) | 165 (3) |
N1—H1A···O10 | 0.91 (3) | 1.96 (3) | 2.844 (3) | 167 (3) |
O12—H12B···O2iv | 0.85 (2) | 2.04 (1) | 2.889 (3) | 177 (3) |
O11—H11B···O9v | 0.85 (3) | 1.95 (3) | 2.765 (3) | 162 (3) |
N3—H3···O12 | 0.90 (3) | 1.96 (3) | 2.845 (3) | 165 (3) |
O8—H8···N4 | 0.82 | 1.87 | 2.589 (3) | 146 |
O6—H6···O9vi | 0.82 | 2.04 | 2.834 (3) | 161 |
O5—H5···O3vi | 0.82 | 1.86 | 2.670 (3) | 170 |
O4—H4···N2 | 0.82 | 1.84 | 2.561 (3) | 146 |
O2—H2···O1 | 0.82 | 2.29 | 2.725 (3) | 114 |
O2—H2···O11vii | 0.82 | 1.93 | 2.703 (3) | 158 |
O1—H1···O7vii | 0.82 | 1.88 | 2.695 (3) | 172 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z+1; (iii) −x+2, −y+1, −z+1; (iv) x, y−1, z−1; (v) x, y+1, z; (vi) x, y, z−1; (vii) x, y, z+1. |
Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the structure of Schiff base compounds (Diao, 2007; Diao et al., 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.
The asymmetric unit of the title compound consists of two Schiff base molecules, three water molecules and one methanol molecule (Fig. 1). The corresponding bond lengths and angles in the two Schiff base molecules are nearly identical. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 7.8 (2)° and that between the C15—C20 and C23—C28 benzene rings is 4.0 (2)°. The structure of each molecule is stabilized by O—H···O and O—H···N intramolecular hydrogen bonds.
In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).