



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809005297/hb2911sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809005297/hb2911Isup2.hkl |
CCDC reference: 722950
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.084
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1041 Count of symmetry unique reflns 1042 Completeness (_total/calc) 99.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
3-Methoxy-2-hydroxybenzaldehyde (0.152 g, 1 mmol) and equimolar 2-aminoethanol (0.061 g, 1 mmol) were refluxed for 30 min in methanol solution (15 ml). The reaction mixtures were cooled to room temprature and filtered. After keeping the filtrate in air for 3 d, yellow blocks of (I) (yield 66%; mp 338–339 K) were obtained.
H atoms were placed at calculated positions and refined in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for sp2 H atoms, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene H atoms, N—H = 0.86 Å and Uiso(H) = 1.2Ueq(C) for imino group, and O—H = 0.82 Å and Uiso(H) = 1.5Ueq(C) for hydroxy. Friedel pairs were merged.
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![]() | Fig. 1. The structure of (I) with displacement ellipsoids drawn at the 50% probability level. The N—H···O hydrogen bond is shown as a dashed line. |
C10H13NO3 | F(000) = 416 |
Mr = 195.21 | Dx = 1.293 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 1828 reflections |
a = 14.148 (6) Å | θ = 2.9–20.4° |
b = 6.587 (3) Å | µ = 0.10 mm−1 |
c = 10.760 (4) Å | T = 295 K |
V = 1002.8 (7) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.30 × 0.12 mm |
Bruker APEX CCD diffractometer | 1041 independent reflections |
Radiation source: fine-focus sealed tube | 923 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −17→17 |
Tmin = 0.974, Tmax = 0.991 | k = −8→8 |
7345 measured reflections | l = −12→13 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0337P] where P = (Fo2 + 2Fc2)/3 |
1041 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.09 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
C10H13NO3 | V = 1002.8 (7) Å3 |
Mr = 195.21 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 14.148 (6) Å | µ = 0.10 mm−1 |
b = 6.587 (3) Å | T = 295 K |
c = 10.760 (4) Å | 0.30 × 0.30 × 0.12 mm |
Bruker APEX CCD diffractometer | 1041 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 923 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.991 | Rint = 0.037 |
7345 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 1 restraint |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.09 e Å−3 |
1041 reflections | Δρmin = −0.15 e Å−3 |
127 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 | ||
C1 | 0.53278 (16) | 0.7444 (3) | 0.0860 (2) | 0.0408 (5) | |
C2 | 0.57651 (16) | 0.9338 (3) | 0.0535 (2) | 0.0451 (6) | |
C3 | 0.69788 (18) | 1.1717 (4) | 0.1022 (3) | 0.0718 (9) | |
H3A | 0.6519 | 1.2763 | 0.1164 | 0.108* | |
H3B | 0.7207 | 1.1807 | 0.0183 | 0.108* | |
H3C | 0.7497 | 1.1885 | 0.1588 | 0.108* | |
C4 | 0.5396 (2) | 1.0535 (4) | −0.0390 (3) | 0.0557 (7) | |
H4 | 0.5680 | 1.1776 | −0.0566 | 0.067* | |
C5 | 0.4599 (2) | 0.9927 (5) | −0.1078 (3) | 0.0625 (8) | |
H5 | 0.4366 | 1.0750 | −0.1710 | 0.075* | |
C6 | 0.41744 (18) | 0.8135 (4) | −0.0814 (3) | 0.0570 (7) | |
H6 | 0.3655 | 0.7718 | −0.1278 | 0.068* | |
C7 | 0.45145 (15) | 0.6891 (4) | 0.0160 (2) | 0.0436 (5) | |
C8 | 0.39971 (16) | 0.5130 (4) | 0.0485 (2) | 0.0460 (6) | |
H8 | 0.3479 | 0.4790 | −0.0006 | 0.055* | |
C9 | 0.36073 (17) | 0.2262 (4) | 0.1804 (3) | 0.0535 (6) | |
H9A | 0.4005 | 0.1091 | 0.1961 | 0.064* | |
H9B | 0.3173 | 0.1915 | 0.1140 | 0.064* | |
C10 | 0.30532 (16) | 0.2758 (4) | 0.2962 (3) | 0.0529 (6) | |
H10A | 0.2717 | 0.1553 | 0.3232 | 0.064* | |
H10B | 0.3490 | 0.3137 | 0.3617 | 0.064* | |
N1 | 0.41934 (14) | 0.3958 (3) | 0.1415 (2) | 0.0478 (5) | |
H1 | 0.4701 | 0.4199 | 0.1829 | 0.057* | |
O1 | 0.56592 (11) | 0.6322 (2) | 0.17429 (18) | 0.0486 (4) | |
O2 | 0.65545 (11) | 0.9784 (3) | 0.1213 (2) | 0.0564 (5) | |
O3 | 0.23996 (12) | 0.4345 (2) | 0.2785 (2) | 0.0584 (5) | |
H3 | 0.1946 | 0.3924 | 0.2387 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0358 (11) | 0.0387 (12) | 0.0478 (13) | 0.0046 (9) | 0.0063 (10) | −0.0074 (11) |
C2 | 0.0393 (12) | 0.0407 (13) | 0.0553 (16) | 0.0030 (10) | 0.0127 (11) | −0.0106 (12) |
C3 | 0.0623 (17) | 0.0421 (15) | 0.111 (3) | −0.0143 (14) | 0.0175 (19) | −0.0154 (16) |
C4 | 0.0608 (17) | 0.0435 (14) | 0.0629 (17) | 0.0038 (13) | 0.0206 (15) | 0.0050 (13) |
C5 | 0.0670 (18) | 0.0703 (19) | 0.0502 (16) | 0.0090 (15) | 0.0064 (14) | 0.0132 (15) |
C6 | 0.0507 (14) | 0.0726 (18) | 0.0477 (15) | 0.0022 (13) | −0.0017 (12) | 0.0014 (14) |
C7 | 0.0378 (12) | 0.0484 (13) | 0.0445 (13) | 0.0014 (11) | 0.0028 (10) | −0.0071 (12) |
C8 | 0.0341 (12) | 0.0521 (14) | 0.0520 (14) | 0.0004 (10) | −0.0026 (11) | −0.0117 (12) |
C9 | 0.0420 (13) | 0.0424 (13) | 0.0760 (18) | −0.0020 (10) | −0.0002 (14) | 0.0002 (13) |
C10 | 0.0422 (12) | 0.0533 (15) | 0.0633 (16) | 0.0033 (11) | −0.0071 (12) | 0.0138 (13) |
N1 | 0.0354 (10) | 0.0481 (12) | 0.0600 (14) | −0.0036 (9) | −0.0025 (9) | −0.0050 (11) |
O1 | 0.0400 (8) | 0.0440 (9) | 0.0619 (11) | −0.0040 (7) | −0.0082 (8) | 0.0003 (9) |
O2 | 0.0436 (9) | 0.0433 (9) | 0.0822 (14) | −0.0083 (8) | 0.0020 (9) | −0.0062 (9) |
O3 | 0.0410 (9) | 0.0591 (10) | 0.0750 (13) | 0.0088 (9) | −0.0069 (9) | −0.0038 (10) |
C1—O1 | 1.291 (3) | C6—H6 | 0.9300 |
C1—C7 | 1.423 (3) | C7—C8 | 1.416 (3) |
C1—C2 | 1.436 (3) | C8—N1 | 1.294 (3) |
C2—O2 | 1.366 (3) | C8—H8 | 0.9300 |
C2—C4 | 1.373 (4) | C9—N1 | 1.453 (3) |
C3—O2 | 1.422 (3) | C9—C10 | 1.508 (4) |
C3—H3A | 0.9600 | C9—H9A | 0.9700 |
C3—H3B | 0.9600 | C9—H9B | 0.9700 |
C3—H3C | 0.9600 | C10—O3 | 1.409 (3) |
C4—C5 | 1.407 (4) | C10—H10A | 0.9700 |
C4—H4 | 0.9300 | C10—H10B | 0.9700 |
C5—C6 | 1.355 (4) | N1—H1 | 0.8600 |
C5—H5 | 0.9300 | O3—H3 | 0.8200 |
C6—C7 | 1.415 (4) | ||
O1—C1—C7 | 122.5 (2) | C6—C7—C1 | 121.3 (2) |
O1—C1—C2 | 121.3 (2) | C8—C7—C1 | 119.8 (2) |
C7—C1—C2 | 116.2 (2) | N1—C8—C7 | 124.6 (2) |
O2—C2—C4 | 125.1 (2) | N1—C8—H8 | 117.7 |
O2—C2—C1 | 114.1 (2) | C7—C8—H8 | 117.7 |
C4—C2—C1 | 120.8 (2) | N1—C9—C10 | 111.6 (2) |
O2—C3—H3A | 109.5 | N1—C9—H9A | 109.3 |
O2—C3—H3B | 109.5 | C10—C9—H9A | 109.3 |
H3A—C3—H3B | 109.5 | N1—C9—H9B | 109.3 |
O2—C3—H3C | 109.5 | C10—C9—H9B | 109.3 |
H3A—C3—H3C | 109.5 | H9A—C9—H9B | 108.0 |
H3B—C3—H3C | 109.5 | O3—C10—C9 | 113.0 (2) |
C2—C4—C5 | 121.5 (2) | O3—C10—H10A | 109.0 |
C2—C4—H4 | 119.2 | C9—C10—H10A | 109.0 |
C5—C4—H4 | 119.2 | O3—C10—H10B | 109.0 |
C6—C5—C4 | 119.5 (3) | C9—C10—H10B | 109.0 |
C6—C5—H5 | 120.2 | H10A—C10—H10B | 107.8 |
C4—C5—H5 | 120.2 | C8—N1—C9 | 124.0 (2) |
C5—C6—C7 | 120.6 (3) | C8—N1—H1 | 118.0 |
C5—C6—H6 | 119.7 | C9—N1—H1 | 118.0 |
C7—C6—H6 | 119.7 | C2—O2—C3 | 117.4 (2) |
C6—C7—C8 | 118.8 (2) | C10—O3—H3 | 109.5 |
O1—C1—C2—O2 | 1.6 (3) | C2—C1—C7—C6 | 1.1 (3) |
C7—C1—C2—O2 | −178.65 (19) | O1—C1—C7—C8 | 4.8 (3) |
O1—C1—C2—C4 | −178.8 (2) | C2—C1—C7—C8 | −175.0 (2) |
C7—C1—C2—C4 | 1.0 (3) | C6—C7—C8—N1 | −174.5 (2) |
O2—C2—C4—C5 | 177.5 (2) | C1—C7—C8—N1 | 1.8 (3) |
C1—C2—C4—C5 | −2.1 (3) | N1—C9—C10—O3 | 63.7 (3) |
C2—C4—C5—C6 | 1.0 (4) | C7—C8—N1—C9 | 174.2 (2) |
C4—C5—C6—C7 | 1.2 (4) | C10—C9—N1—C8 | −104.5 (3) |
C5—C6—C7—C8 | 174.0 (2) | C4—C2—O2—C3 | 5.8 (3) |
C5—C6—C7—C1 | −2.2 (4) | C1—C2—O2—C3 | −174.6 (2) |
O1—C1—C7—C6 | −179.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.95 | 2.617 (2) | 134 |
O3—H3···O1i | 0.82 | 1.95 | 2.741 (3) | 161 |
Symmetry code: (i) x−1/2, −y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H13NO3 |
Mr | 195.21 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 295 |
a, b, c (Å) | 14.148 (6), 6.587 (3), 10.760 (4) |
V (Å3) | 1002.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.30 × 0.12 |
Data collection | |
Diffractometer | Bruker APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.974, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7345, 1041, 923 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.084, 1.07 |
No. of reflections | 1041 |
No. of parameters | 127 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.09, −0.15 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.95 | 2.617 (2) | 134 |
O3—H3···O1i | 0.82 | 1.95 | 2.741 (3) | 161 |
Symmetry code: (i) x−1/2, −y+1, z. |
The title compound, (I), derived from 3-methoxy-2-hydroxybenzaldehyde and 2-aminoethanol, is a potential NO3 tetradentate Schiff base ligand and its complexes with Cd(II), Cu(II), Zn(II) and Fe(III) have been reported (Cui et al., 1999; Dong et al., 2007; Li et al., 2005; Oshio et al., 2003). Here, the structure of (I) is described.
The title molecule exists in a zwitterionic form with a strong intramolecular N—H···O hydrogen bond (Table 1) between the NH+ and the phenolate O-, as shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al.,1987). The N1=C8 [1.294 (3) Å] and N1—C8 [1.453 (3) Å] bond distances are comparable to these found in similar Schiff base compounds, such as 2,4-Dibromo-6-(2-hydroxyethyliminiomethyl)- phenolate [1.277 (5) and 1.451 (4) Å] (Sun et al., 2006) and 4-chloro-2-[tris(hydroxymethyl)methyliminiomethyl]phenolate [1.288 (2) and 1.467 (2) Å] (Ng, 2008). As expected, the molecule adopts a trans configuration about the central C=N bond. In the crystal structure, O3—H3···O1i (symmetry code as given in Table 1) intermolecular hydrogen bonds formed between the hydroxy and oxygen of phenolate link the molecules into a one-dimension supramolecular chain.