Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040329/hk2286sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040329/hk2286Isup2.hkl |
CCDC reference: 660128
The title compound was prepared by the literature method (Parekh & Patel, 2005). The resulting solid was recrystallized from ethanol-ether (1:1) mixture to give suitable crystals of (I) for X-ray analysis (yield; 65%).
H3 and H4A (for OH groups) were located in difference syntheses and refined isotropically [O3—H3 = 0.79 (3) Å, Uiso(H) = 0.053 (8) Å2 and O4—H4A = 0.85 (3) Å, Uiso(H) = 0.087 (11) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
The title compound, (I), is an effective material for preparing rare earth complexes (Parekh & Patel, 2005). We herein report its crystal structure.
In the molecule of (I) (Fig. 1), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). Intramolecular O—H···N hydrogen bonding (Table 2) results in the formation of planar five-membered ring A (O4/H4/N1/C4–C6). Ring B (C5–C10) is, of course, planar and the dihedral angle between planes A and B is 3.56 (4)°. On the other hand, the C2/C4–C10/N1/O4 unit is nearly planar, with an r.m.s. deviation of 0.0425 Å.
In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2 and Fig. 2) result in the formation of chains along the c axis.
For bond-length data, see: Allen et al. (1987). For related literature, see: Parekh & Patel (2005).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
[K(C10H10NO4)] | F(000) = 512 |
Mr = 247.29 | Dx = 1.504 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 1145 reflections |
a = 7.9571 (6) Å | θ = 3.0–25.1° |
b = 17.7596 (13) Å | µ = 0.48 mm−1 |
c = 7.7258 (6) Å | T = 291 K |
V = 1091.77 (14) Å3 | Block, yellow |
Z = 4 | 0.16 × 0.12 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1782 independent reflections |
Radiation source: fine-focus sealed tube | 1689 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.927, Tmax = 0.953 | k = −20→21 |
5642 measured reflections | l = −9→7 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.0126P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
1782 reflections | Δρmax = 0.17 e Å−3 |
153 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 630 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (4) |
[K(C10H10NO4)] | V = 1091.77 (14) Å3 |
Mr = 247.29 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 7.9571 (6) Å | µ = 0.48 mm−1 |
b = 17.7596 (13) Å | T = 291 K |
c = 7.7258 (6) Å | 0.16 × 0.12 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 1782 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1689 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.953 | Rint = 0.027 |
5642 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | Δρmax = 0.17 e Å−3 |
S = 1.06 | Δρmin = −0.13 e Å−3 |
1782 reflections | Absolute structure: Flack (1983), 630 Friedel pairs |
153 parameters | Absolute structure parameter: −0.06 (4) |
1 restraint |
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 | ||
K1 | 0.91131 (5) | 1.03625 (2) | 1.40599 (7) | 0.04057 (13) | |
O1 | 0.86842 (16) | 1.08264 (8) | 1.0595 (2) | 0.0402 (3) | |
O2 | 1.13102 (19) | 1.09544 (8) | 1.1450 (2) | 0.0440 (4) | |
O3 | 1.0429 (2) | 1.10354 (8) | 0.70054 (19) | 0.0427 (4) | |
H3 | 1.141 (3) | 1.1124 (14) | 0.700 (4) | 0.053 (8)* | |
O4 | 1.49653 (19) | 1.22892 (9) | 0.8458 (2) | 0.0483 (4) | |
H4A | 1.400 (4) | 1.2107 (18) | 0.872 (6) | 0.087 (11)* | |
N1 | 1.18204 (19) | 1.22190 (8) | 0.9470 (2) | 0.0345 (4) | |
C1 | 1.0058 (2) | 1.11657 (10) | 1.0608 (3) | 0.0309 (4) | |
C2 | 1.0143 (2) | 1.18757 (11) | 0.9488 (3) | 0.0339 (4) | |
H2 | 0.9347 | 1.2244 | 0.9955 | 0.041* | |
C3 | 0.9613 (3) | 1.16839 (12) | 0.7653 (3) | 0.0387 (5) | |
H3A | 0.8408 | 1.1603 | 0.7628 | 0.046* | |
H3B | 0.9864 | 1.2108 | 0.6904 | 0.046* | |
C4 | 1.1984 (2) | 1.28810 (11) | 1.0049 (3) | 0.0392 (5) | |
H4 | 1.1057 | 1.3115 | 1.0546 | 0.047* | |
C5 | 1.3570 (3) | 1.32923 (11) | 0.9967 (3) | 0.0405 (5) | |
C6 | 1.4980 (2) | 1.29850 (11) | 0.9128 (3) | 0.0412 (4) | |
C7 | 1.6432 (3) | 1.34175 (13) | 0.8968 (5) | 0.0607 (6) | |
H7 | 1.7358 | 1.3227 | 0.8378 | 0.073* | |
C8 | 1.6498 (4) | 1.41259 (15) | 0.9681 (5) | 0.0789 (10) | |
H8 | 1.7470 | 1.4411 | 0.9560 | 0.095* | |
C9 | 1.5147 (4) | 1.44216 (14) | 1.0573 (6) | 0.0828 (10) | |
H9 | 1.5219 | 1.4897 | 1.1070 | 0.099* | |
C10 | 1.3691 (3) | 1.40066 (12) | 1.0720 (5) | 0.0609 (7) | |
H10 | 1.2780 | 1.4203 | 1.1324 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.0396 (2) | 0.0493 (2) | 0.0329 (2) | 0.00844 (17) | 0.00437 (19) | 0.0037 (2) |
O1 | 0.0326 (7) | 0.0483 (8) | 0.0398 (8) | −0.0112 (6) | −0.0002 (7) | 0.0046 (6) |
O2 | 0.0336 (7) | 0.0456 (8) | 0.0527 (10) | −0.0037 (6) | −0.0075 (7) | 0.0111 (7) |
O3 | 0.0347 (7) | 0.0539 (9) | 0.0396 (9) | −0.0066 (7) | 0.0036 (7) | −0.0091 (7) |
O4 | 0.0450 (9) | 0.0563 (10) | 0.0435 (9) | −0.0054 (7) | 0.0029 (7) | −0.0065 (7) |
N1 | 0.0340 (8) | 0.0359 (8) | 0.0335 (10) | −0.0056 (6) | 0.0020 (6) | 0.0014 (6) |
C1 | 0.0285 (9) | 0.0362 (9) | 0.0279 (10) | −0.0004 (7) | 0.0023 (8) | −0.0031 (8) |
C2 | 0.0297 (9) | 0.0363 (9) | 0.0356 (11) | −0.0003 (7) | 0.0040 (7) | 0.0007 (8) |
C3 | 0.0352 (10) | 0.0464 (11) | 0.0346 (11) | −0.0021 (8) | −0.0007 (8) | 0.0062 (9) |
C4 | 0.0395 (11) | 0.0370 (11) | 0.0411 (12) | −0.0005 (8) | 0.0036 (9) | 0.0045 (8) |
C5 | 0.0464 (11) | 0.0328 (10) | 0.0424 (12) | −0.0067 (8) | −0.0073 (9) | 0.0062 (8) |
C6 | 0.0413 (11) | 0.0452 (10) | 0.0371 (11) | −0.0061 (7) | −0.0066 (10) | 0.0115 (10) |
C7 | 0.0429 (11) | 0.0652 (14) | 0.0741 (17) | −0.0118 (10) | −0.0057 (15) | 0.0092 (16) |
C8 | 0.0565 (15) | 0.0589 (16) | 0.121 (3) | −0.0256 (12) | −0.0184 (18) | 0.0143 (15) |
C9 | 0.0706 (19) | 0.0418 (14) | 0.136 (3) | −0.0157 (12) | −0.021 (2) | −0.0080 (18) |
C10 | 0.0587 (14) | 0.0380 (12) | 0.086 (2) | −0.0021 (10) | −0.0047 (15) | −0.0068 (12) |
K1—O1i | 2.6533 (14) | C4—N1 | 1.265 (2) |
K1—O3ii | 2.7755 (16) | C4—C5 | 1.460 (3) |
K1—O1 | 2.8215 (16) | C4—H4 | 0.9300 |
K1—O2 | 2.8685 (17) | C5—C10 | 1.399 (3) |
K1—O3iii | 2.9691 (16) | C5—C6 | 1.406 (3) |
K1—O1iii | 2.9896 (15) | C6—O4 | 1.340 (3) |
K1—O2iii | 2.9986 (17) | C6—C7 | 1.393 (3) |
K1—C1iii | 3.0384 (19) | C7—C8 | 1.374 (4) |
K1—K1iv | 4.1817 (4) | C7—H7 | 0.9300 |
K1—K1v | 4.1817 (4) | C8—C9 | 1.380 (5) |
K1—K1vi | 4.3095 (4) | C8—H8 | 0.9300 |
K1—K1iii | 4.3095 (4) | C9—C10 | 1.378 (4) |
C1—O2 | 1.248 (2) | C9—H9 | 0.9300 |
C1—O1 | 1.248 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.531 (3) | O1—K1vii | 2.6533 (14) |
C1—K1vi | 3.0384 (19) | O1—K1vi | 2.9896 (15) |
C2—N1 | 1.468 (2) | O2—K1vi | 2.9986 (17) |
C2—C3 | 1.517 (3) | O3—K1viii | 2.7755 (16) |
C2—H2 | 0.9800 | O3—K1vi | 2.9691 (16) |
C3—O3 | 1.414 (3) | O3—H3 | 0.79 (3) |
C3—H3A | 0.9700 | O4—H4A | 0.85 (3) |
C3—H3B | 0.9700 | ||
O1i—K1—O3ii | 79.42 (5) | O2iii—K1—K1iii | 41.57 (3) |
O1i—K1—O1 | 103.41 (4) | C1iii—K1—K1iii | 46.30 (4) |
O3ii—K1—O1 | 134.25 (4) | K1iv—K1—K1iii | 102.687 (14) |
O1i—K1—O2 | 135.38 (4) | K1v—K1—K1iii | 66.196 (10) |
O3ii—K1—O2 | 100.87 (5) | K1vi—K1—K1iii | 127.367 (19) |
O1—K1—O2 | 45.55 (4) | O2—C1—O1 | 123.94 (19) |
O1i—K1—O3iii | 126.98 (5) | O2—C1—C2 | 120.46 (16) |
O3ii—K1—O3iii | 138.77 (3) | O1—C1—C2 | 115.60 (16) |
O1—K1—O3iii | 75.63 (4) | O2—C1—K1vi | 76.29 (11) |
O2—K1—O3iii | 81.71 (4) | O1—C1—K1vi | 75.87 (11) |
O1i—K1—O1iii | 122.26 (6) | C2—C1—K1vi | 120.25 (12) |
O3ii—K1—O1iii | 75.97 (4) | N1—C2—C3 | 109.69 (15) |
O1—K1—O1iii | 130.81 (4) | N1—C2—C1 | 112.83 (15) |
O2—K1—O1iii | 100.39 (4) | C3—C2—C1 | 109.32 (16) |
O3iii—K1—O1iii | 63.23 (4) | N1—C2—H2 | 108.3 |
O1i—K1—O2iii | 82.69 (4) | C3—C2—H2 | 108.3 |
O3ii—K1—O2iii | 82.73 (5) | C1—C2—H2 | 108.3 |
O1—K1—O2iii | 142.97 (4) | O3—C3—C2 | 112.71 (17) |
O2—K1—O2iii | 141.92 (2) | O3—C3—H3A | 109.0 |
O3iii—K1—O2iii | 71.99 (4) | C2—C3—H3A | 109.0 |
O1iii—K1—O2iii | 43.17 (4) | O3—C3—H3B | 109.0 |
O1i—K1—C1iii | 106.48 (5) | C2—C3—H3B | 109.0 |
O3ii—K1—C1iii | 88.85 (5) | H3A—C3—H3B | 107.8 |
O1—K1—C1iii | 131.34 (5) | N1—C4—C5 | 122.61 (18) |
O2—K1—C1iii | 118.14 (5) | N1—C4—H4 | 118.7 |
O3iii—K1—C1iii | 55.73 (5) | C5—C4—H4 | 118.7 |
O1iii—K1—C1iii | 23.88 (4) | C10—C5—C6 | 119.3 (2) |
O2iii—K1—C1iii | 23.85 (4) | C10—C5—C4 | 119.7 (2) |
O1i—K1—K1iv | 45.37 (3) | C6—C5—C4 | 121.05 (18) |
O3ii—K1—K1iv | 119.44 (3) | O4—C6—C7 | 118.8 (2) |
O1—K1—K1iv | 88.56 (3) | O4—C6—C5 | 121.93 (17) |
O2—K1—K1iv | 133.84 (3) | C7—C6—C5 | 119.3 (2) |
O3iii—K1—K1iv | 81.91 (3) | C8—C7—C6 | 120.0 (3) |
O1iii—K1—K1iv | 109.90 (3) | C8—C7—H7 | 120.0 |
O2iii—K1—K1iv | 69.70 (3) | C6—C7—H7 | 120.0 |
C1iii—K1—K1iv | 86.08 (4) | C7—C8—C9 | 121.2 (2) |
O1i—K1—K1v | 153.35 (3) | C7—C8—H8 | 119.4 |
O3ii—K1—K1v | 76.91 (3) | C9—C8—H8 | 119.4 |
O1—K1—K1v | 101.83 (3) | C10—C9—C8 | 119.5 (3) |
O2—K1—K1v | 62.16 (3) | C10—C9—H9 | 120.2 |
O3iii—K1—K1v | 68.03 (3) | C8—C9—H9 | 120.2 |
O1iii—K1—K1v | 39.17 (3) | C9—C10—C5 | 120.6 (3) |
O2iii—K1—K1v | 82.34 (3) | C9—C10—H10 | 119.7 |
C1iii—K1—K1v | 61.21 (3) | C5—C10—H10 | 119.7 |
K1iv—K1—K1v | 144.13 (2) | C4—N1—C2 | 118.45 (16) |
O1i—K1—K1vi | 140.20 (4) | C1—O1—K1vii | 152.63 (14) |
O3ii—K1—K1vi | 137.73 (4) | C1—O1—K1 | 91.58 (12) |
O1—K1—K1vi | 43.65 (3) | K1vii—O1—K1 | 115.78 (5) |
O2—K1—K1vi | 43.92 (3) | C1—O1—K1vi | 80.25 (10) |
O3iii—K1—K1vi | 39.72 (3) | K1vii—O1—K1vi | 95.46 (4) |
O1iii—K1—K1vi | 87.28 (3) | K1—O1—K1vi | 95.69 (4) |
O2iii—K1—K1vi | 110.83 (3) | C1—O2—K1 | 89.42 (12) |
C1iii—K1—K1vi | 90.85 (4) | C1—O2—K1vi | 79.86 (11) |
K1iv—K1—K1vi | 102.687 (14) | K1—O2—K1vi | 94.51 (4) |
K1v—K1—K1vi | 66.196 (10) | C3—O3—K1viii | 117.90 (12) |
O1i—K1—K1iii | 88.10 (3) | C3—O3—K1vi | 123.25 (12) |
O3ii—K1—K1iii | 43.13 (3) | K1viii—O3—K1vi | 97.15 (4) |
O1—K1—K1iii | 167.76 (3) | C3—O3—H3 | 106.8 (18) |
O2—K1—K1iii | 122.68 (4) | K1viii—O3—H3 | 117 (2) |
O3iii—K1—K1iii | 100.91 (3) | K1vi—O3—H3 | 92.8 (18) |
O1iii—K1—K1iii | 40.65 (3) | C6—O4—H4A | 106 (2) |
Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, z+1/2; (iv) x−1/2, −y+2, z; (v) x+1/2, −y+2, z; (vi) −x+2, −y+2, z−1/2; (vii) −x+3/2, y, z−1/2; (viii) x, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2ix | 0.80 (2) | 1.89 (2) | 2.634 (2) | 156 (3) |
O4—H4A···N1 | 0.86 (3) | 1.84 (3) | 2.625 (2) | 151 (3) |
Symmetry code: (ix) −x+5/2, y, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [K(C10H10NO4)] |
Mr | 247.29 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 291 |
a, b, c (Å) | 7.9571 (6), 17.7596 (13), 7.7258 (6) |
V (Å3) | 1091.77 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.16 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.927, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5642, 1782, 1689 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.068, 1.06 |
No. of reflections | 1782 |
No. of parameters | 153 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.13 |
Absolute structure | Flack (1983), 630 Friedel pairs |
Absolute structure parameter | −0.06 (4) |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
K1—O1i | 2.6533 (14) | K1—C1iii | 3.0384 (19) |
K1—O3ii | 2.7755 (16) | C1—O2 | 1.248 (2) |
K1—O1 | 2.8215 (16) | C1—O1 | 1.248 (2) |
K1—O2 | 2.8685 (17) | C2—N1 | 1.468 (2) |
K1—O3iii | 2.9691 (16) | C3—O3 | 1.414 (3) |
K1—O1iii | 2.9896 (15) | C4—N1 | 1.265 (2) |
K1—O2iii | 2.9986 (17) | C6—O4 | 1.340 (3) |
O1i—K1—O3ii | 79.42 (5) | O3ii—K1—O1iii | 75.97 (4) |
O1i—K1—O1 | 103.41 (4) | O1—K1—O1iii | 130.81 (4) |
O3ii—K1—O1 | 134.25 (4) | O2—K1—O1iii | 100.39 (4) |
O1i—K1—O2 | 135.38 (4) | O3iii—K1—O1iii | 63.23 (4) |
O3ii—K1—O2 | 100.87 (5) | O1i—K1—O2iii | 82.69 (4) |
O1—K1—O2 | 45.55 (4) | O3ii—K1—O2iii | 82.73 (5) |
O1i—K1—O3iii | 126.98 (5) | O1—K1—O2iii | 142.97 (4) |
O3ii—K1—O3iii | 138.77 (3) | O2—K1—O2iii | 141.92 (2) |
O1—K1—O3iii | 75.63 (4) | O3iii—K1—O2iii | 71.99 (4) |
O2—K1—O3iii | 81.71 (4) | O1iii—K1—O2iii | 43.17 (4) |
O1i—K1—O1iii | 122.26 (6) |
Symmetry codes: (i) −x+3/2, y, z+1/2; (ii) x, y, z+1; (iii) −x+2, −y+2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2iv | 0.80 (2) | 1.89 (2) | 2.634 (2) | 156 (3) |
O4—H4A···N1 | 0.86 (3) | 1.84 (3) | 2.625 (2) | 151 (3) |
Symmetry code: (iv) −x+5/2, y, z−1/2. |
The title compound, (I), is an effective material for preparing rare earth complexes (Parekh & Patel, 2005). We herein report its crystal structure.
In the molecule of (I) (Fig. 1), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). Intramolecular O—H···N hydrogen bonding (Table 2) results in the formation of planar five-membered ring A (O4/H4/N1/C4–C6). Ring B (C5–C10) is, of course, planar and the dihedral angle between planes A and B is 3.56 (4)°. On the other hand, the C2/C4–C10/N1/O4 unit is nearly planar, with an r.m.s. deviation of 0.0425 Å.
In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 2 and Fig. 2) result in the formation of chains along the c axis.