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The title complex, [Zn(C10H6NO2)2(H2O)2]·2H2O, has a distorted octahedral coordination, in which the ZnII atom lies on a centre of symmetry. The coordination bond length of the aqua O atom, 2.208 (2) Å, in the axial direction is longer than those of the carboxylato O atom and the ring N atom of the bidentate isoquinoline-1-carboxylate ligand in the equatorial plane [2.068 (2) and 2.084 (3) Å, respectively].
Supporting information
CCDC reference: 214564
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.129
- Data-to-parameter ratio = 15.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(1) - C(10) = 1.54 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Colorless plate-shaped crystals of (I) were obtained by slow evaporation of a methanol–water solution (90:10%, v/v) of a mixture of isoquinoline-1-carboxylic acid and ZnSO4·7H2O (molar ratio 4:1).
H atoms were treated by riding models.
Data collection: MSC/AFC (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC (Molecular Structure Corporation, 1992); data reduction: TEXSAN (Molecular Structure Corporation, Rigaku Corporation, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999) & DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Scheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[Zn(C10H6NO2)2(H2O)2]·2H2O | F(000) = 496.0 |
Mr = 481.77 | Dx = 1.628 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 12.224 (1) Å | θ = 12.8–14.5° |
b = 5.341 (2) Å | µ = 1.30 mm−1 |
c = 15.191 (1) Å | T = 296 K |
β = 97.625 (7)° | Plate, colorless |
V = 983.0 (4) Å3 | 0.30 × 0.10 × 0.05 mm |
Z = 2 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.026 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = 0→15 |
Tmin = 0.855, Tmax = 0.937 | k = 0→6 |
2598 measured reflections | l = −19→19 |
2247 independent reflections | 3 standard reflections every 150 reflections |
1477 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement top
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.129 | (Δ/σ)max < 0.001 |
S = 0.82 | Δρmax = 0.32 e Å−3 |
2247 reflections | Δρmin = −0.33 e Å−3 |
142 parameters | |
Crystal data top
[Zn(C10H6NO2)2(H2O)2]·2H2O | V = 983.0 (4) Å3 |
Mr = 481.77 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.224 (1) Å | µ = 1.30 mm−1 |
b = 5.341 (2) Å | T = 296 K |
c = 15.191 (1) Å | 0.30 × 0.10 × 0.05 mm |
β = 97.625 (7)° | |
Data collection top
Rigaku AFC-5R diffractometer | 1477 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.026 |
Tmin = 0.855, Tmax = 0.937 | 3 standard reflections every 150 reflections |
2598 measured reflections | intensity decay: 0.4% |
2247 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.036 | 142 parameters |
wR(F2) = 0.129 | H-atom parameters not refined |
S = 0.82 | Δρmax = 0.32 e Å−3 |
2247 reflections | Δρmin = −0.33 e Å−3 |
Special details top
Refinement. Refinement using reflections with F2 > −10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.5000 | 0.5000 | 0.5000 | 0.0264 (2) | |
O1 | 0.3933 (2) | 0.2219 (4) | 0.4469 (2) | 0.0303 (5) | |
O1W | 0.4452 (2) | 0.7422 (5) | 0.3848 (2) | 0.0337 (5) | |
O2 | 0.2180 (2) | 0.1079 (6) | 0.4315 (2) | 0.0429 (6) | |
O2W | 0.2002 (3) | 0.0193 (5) | 0.2538 (2) | 0.0503 (7) | |
N1 | 0.3594 (2) | 0.5840 (5) | 0.5583 (2) | 0.0243 (5) | |
C1 | 0.2756 (2) | 0.4290 (6) | 0.5373 (2) | 0.0230 (6) | |
C2 | 0.1770 (2) | 0.4453 (6) | 0.5775 (2) | 0.0243 (7) | |
C3 | 0.0875 (3) | 0.2744 (7) | 0.5626 (2) | 0.0329 (7) | |
C4 | −0.0027 (3) | 0.3026 (7) | 0.6068 (2) | 0.0382 (8) | |
C5 | −0.0097 (3) | 0.5038 (8) | 0.6654 (2) | 0.0398 (8) | |
C6 | 0.0740 (3) | 0.6715 (7) | 0.6807 (2) | 0.0350 (8) | |
C7 | 0.1691 (3) | 0.6463 (6) | 0.6382 (2) | 0.0267 (6) | |
C8 | 0.2596 (3) | 0.8088 (7) | 0.6562 (2) | 0.0330 (7) | |
C9 | 0.3518 (3) | 0.7722 (7) | 0.6173 (2) | 0.0324 (7) | |
C10 | 0.2962 (3) | 0.2363 (6) | 0.4663 (2) | 0.0261 (6) | |
H1A | 0.4217 | 0.8767 | 0.3989 | 0.0404* | |
H1B | 0.3981 | 0.6783 | 0.3478 | 0.0404* | |
H2A | 0.2059 | 0.0370 | 0.3078 | 0.0604* | |
H2B | 0.2097 | −0.1297 | 0.2442 | 0.0604* | |
H3 | 0.0900 | 0.1429 | 0.5228 | 0.0395* | |
H4 | −0.0600 | 0.1869 | 0.5978 | 0.0459* | |
H5 | −0.0720 | 0.5220 | 0.6939 | 0.0478* | |
H6 | 0.0686 | 0.8041 | 0.7196 | 0.0420* | |
H8 | 0.2562 | 0.9424 | 0.6950 | 0.0396* | |
H9 | 0.4117 | 0.8789 | 0.6315 | 0.0389* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0205 (2) | 0.0282 (3) | 0.0316 (3) | −0.0045 (2) | 0.0075 (2) | −0.0059 (3) |
O1 | 0.025 (1) | 0.030 (1) | 0.038 (1) | −0.0048 (9) | 0.0086 (9) | −0.012 (1) |
O1W | 0.036 (1) | 0.030 (1) | 0.035 (1) | 0.004 (1) | 0.0033 (9) | −0.001 (1) |
O2 | 0.031 (1) | 0.056 (2) | 0.044 (1) | −0.017 (1) | 0.010 (1) | −0.024 (1) |
O2W | 0.074 (2) | 0.044 (2) | 0.032 (1) | 0.008 (1) | 0.003 (1) | 0.000 (1) |
N1 | 0.023 (1) | 0.027 (1) | 0.023 (1) | −0.002 (1) | 0.0037 (9) | −0.0035 (10) |
C1 | 0.023 (1) | 0.023 (1) | 0.022 (1) | 0.000 (1) | 0.003 (1) | 0.000 (1) |
C2 | 0.023 (1) | 0.026 (2) | 0.023 (1) | 0.000 (1) | 0.003 (1) | 0.003 (1) |
C3 | 0.027 (2) | 0.035 (2) | 0.037 (2) | −0.004 (1) | 0.008 (1) | −0.005 (1) |
C4 | 0.027 (2) | 0.044 (2) | 0.046 (2) | −0.007 (1) | 0.009 (1) | 0.004 (2) |
C5 | 0.029 (2) | 0.050 (2) | 0.043 (2) | 0.004 (2) | 0.015 (1) | 0.005 (2) |
C6 | 0.035 (2) | 0.037 (2) | 0.035 (2) | 0.006 (1) | 0.011 (1) | 0.000 (1) |
C7 | 0.027 (1) | 0.028 (2) | 0.025 (1) | 0.005 (1) | 0.004 (1) | 0.001 (1) |
C8 | 0.036 (2) | 0.032 (2) | 0.032 (2) | −0.002 (1) | 0.008 (1) | −0.008 (1) |
C9 | 0.031 (2) | 0.031 (2) | 0.035 (2) | −0.006 (1) | 0.003 (1) | −0.009 (1) |
C10 | 0.026 (1) | 0.026 (2) | 0.026 (1) | −0.002 (1) | 0.004 (1) | −0.003 (1) |
Geometric parameters (Å, º) top
Zn1—O1 | 2.068 (2) | C1—C10 | 1.535 (4) |
Zn1—O1i | 2.068 (2) | C2—C3 | 1.420 (4) |
Zn1—O1W | 2.208 (2) | C2—C7 | 1.427 (4) |
Zn1—O1Wi | 2.208 (2) | C3—C4 | 1.373 (5) |
Zn1—N1 | 2.084 (3) | C3—H3 | 0.930 |
Zn1—N1i | 2.084 (3) | C4—C5 | 1.406 (6) |
O1—C10 | 1.264 (4) | C4—H4 | 0.930 |
O1W—H1A | 0.813 | C5—C6 | 1.356 (5) |
O1W—H1B | 0.823 | C5—H5 | 0.930 |
O2—C10 | 1.237 (4) | C6—C7 | 1.410 (5) |
O2W—H2A | 0.820 | C6—H6 | 0.930 |
O2W—H2B | 0.820 | C7—C8 | 1.405 (5) |
N1—C1 | 1.323 (4) | C8—C9 | 1.354 (5) |
N1—C9 | 1.358 (4) | C8—H8 | 0.930 |
C1—C2 | 1.423 (4) | C9—H9 | 0.930 |
| | | |
O1···O1Wii | 2.831 (3) | O2W···O2Wiii | 2.944 (3) |
O1···O2Wiii | 3.492 (3) | O2W···O2Wviii | 2.944 (3) |
O1W···O2Wiii | 2.830 (4) | C2···C4vii | 3.550 (4) |
O1W···C10iv | 3.524 (4) | C3···C8ii | 3.441 (5) |
O1W···O2iv | 3.544 (4) | C3···C4vii | 3.477 (5) |
O1W···C9v | 3.593 (4) | C3···C3vii | 3.594 (7) |
O2···C4vi | 3.415 (4) | C6···C8ix | 3.562 (5) |
O2···C5vii | 3.458 (4) | C9···C10iv | 3.384 (4) |
O2···C9ii | 3.555 (4) | | |
| | | |
O1—Zn1—O1i | 180.00 (1) | C1—C2—C7 | 117.2 (3) |
O1—Zn1—O1W | 90.11 (9) | C3—C2—C7 | 118.0 (3) |
O1—Zn1—O1Wi | 89.89 (9) | C2—C3—C4 | 120.3 (3) |
O1—Zn1—N1 | 78.91 (10) | C2—C3—H3 | 119.9 |
O1—Zn1—N1i | 101.09 (10) | C4—C3—H3 | 119.9 |
O1i—Zn1—O1W | 89.89 (9) | C3—C4—C5 | 120.9 (3) |
O1i—Zn1—O1Wi | 90.11 (9) | C3—C4—H4 | 119.5 |
O1i—Zn1—N1 | 101.09 (10) | C5—C4—H4 | 119.5 |
O1i—Zn1—N1i | 78.91 (10) | C4—C5—C6 | 120.4 (3) |
O1W—Zn1—O1Wi | 180.0 | C4—C5—H5 | 119.8 |
O1W—Zn1—N1 | 91.71 (9) | C6—C5—H5 | 119.8 |
O1W—Zn1—N1i | 88.29 (9) | C5—C6—C7 | 120.5 (3) |
O1Wi—Zn1—N1 | 88.29 (9) | C5—C6—H6 | 119.8 |
O1Wi—Zn1—N1i | 91.71 (9) | C7—C6—H6 | 119.8 |
N1—Zn1—N1i | 180.0 | C2—C7—C6 | 119.9 (3) |
Zn1—O1—C10 | 115.4 (2) | C2—C7—C8 | 118.1 (3) |
Zn1—O1W—H1A | 112.9 | C6—C7—C8 | 121.9 (3) |
Zn1—O1W—H1B | 114.2 | C7—C8—C9 | 120.4 (3) |
H1A—O1W—H1B | 107.9 | C7—C8—H8 | 119.8 |
H2A—O2W—H2B | 107.1 | C9—C8—H8 | 119.8 |
Zn1—N1—C1 | 114.8 (2) | N1—C9—C8 | 121.9 (3) |
Zn1—N1—C9 | 124.9 (2) | N1—C9—H9 | 119.1 |
C1—N1—C9 | 120.2 (3) | C8—C9—H9 | 119.0 |
N1—C1—C2 | 122.1 (3) | O1—C10—O2 | 124.3 (3) |
N1—C1—C10 | 113.2 (3) | O1—C10—C1 | 116.9 (3) |
C2—C1—C10 | 124.7 (3) | O2—C10—C1 | 118.8 (3) |
C1—C2—C3 | 124.8 (3) | | |
| | | |
Zn1—O1—C10—O2 | 169.9 (3) | N1—Zn1—O1—C10 | 4.7 (2) |
Zn1—O1—C10—C1 | −9.3 (3) | N1—Zn1—O1i—C10i | 175.3 (2) |
Zn1—O1i—C10i—O2i | −169.9 (3) | N1—C1—C2—C3 | −175.3 (3) |
Zn1—O1i—C10i—C1i | 9.3 (3) | N1—C1—C2—C7 | 3.6 (4) |
Zn1—N1—C1—C2 | 174.1 (2) | N1—C9—C8—C7 | 1.9 (5) |
Zn1—N1—C1—C10 | −6.2 (3) | C1—N1—C9—C8 | −0.3 (5) |
Zn1—N1—C9—C8 | −176.6 (2) | C1—C2—C3—C4 | 178.0 (3) |
Zn1—N1i—C1i—C2i | −174.1 (2) | C1—C2—C7—C6 | −179.5 (3) |
Zn1—N1i—C1i—C10i | 6.2 (3) | C1—C2—C7—C8 | −1.9 (4) |
Zn1—N1i—C9i—C8i | 176.6 (2) | C2—C1—N1—C9 | −2.5 (4) |
O1—Zn1—N1—C1 | 1.4 (2) | C2—C3—C4—C5 | 1.8 (5) |
O1—Zn1—N1—C9 | 177.9 (3) | C2—C7—C6—C5 | 0.9 (5) |
O1—Zn1—N1i—C1i | 178.6 (2) | C2—C7—C8—C9 | −0.7 (5) |
O1—Zn1—N1i—C9i | 2.1 (3) | C3—C2—C1—C10 | 5.0 (5) |
O1—C10—C1—N1 | 10.5 (4) | C3—C2—C7—C6 | −0.5 (4) |
O1—C10—C1—C2 | −169.8 (3) | C3—C2—C7—C8 | 177.1 (3) |
O1W—Zn1—O1—C10 | −87.0 (2) | C3—C4—C5—C6 | −1.3 (5) |
O1W—Zn1—O1i—C10i | −93.0 (2) | C4—C3—C2—C7 | −0.9 (5) |
O1W—Zn1—N1—C1 | 91.2 (2) | C4—C5—C6—C7 | −0.1 (5) |
O1W—Zn1—N1—C9 | −92.3 (3) | C5—C6—C7—C8 | −176.6 (3) |
O1W—Zn1—N1i—C1i | 88.8 (2) | C6—C7—C8—C9 | 176.8 (3) |
O1W—Zn1—N1i—C9i | −87.7 (3) | C7—C2—C1—C10 | −176.1 (3) |
O2—C10—C1—N1 | −168.8 (3) | C9—N1—C1—C10 | 177.1 (3) |
O2—C10—C1—C2 | 10.9 (5) | C9—N1—C1—C10 | 177.1 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x, y+1, z; (v) −x+1, −y+2, −z+1; (vi) −x, −y, −z+1; (vii) −x, −y+1, −z+1; (viii) −x+1/2, y−1/2, −z+1/2; (ix) −x+1/2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1iv | 0.81 | 2.03 | 2.831 (3) | 169 |
O1W—H1B···O2Wiii | 0.82 | 2.01 | 2.830 (4) | 172 |
O2W—H2A···O2 | 0.82 | 1.90 | 2.721 (4) | 175 |
O2W—H2B···O2Wviii | 0.82 | 2.17 | 2.944 (3) | 157 |
Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) x, y+1, z; (viii) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data |
Chemical formula | [Zn(C10H6NO2)2(H2O)2]·2H2O |
Mr | 481.77 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 12.224 (1), 5.341 (2), 15.191 (1) |
β (°) | 97.625 (7) |
V (Å3) | 983.0 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.30 |
Crystal size (mm) | 0.30 × 0.10 × 0.05 |
|
Data collection |
Diffractometer | Rigaku AFC-5R diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.855, 0.937 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2598, 2247, 1477 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.129, 0.82 |
No. of reflections | 2247 |
No. of parameters | 142 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.33 |
Selected geometric parameters (Å, º) topZn1—O1 | 2.068 (2) | Zn1—N1 | 2.084 (3) |
Zn1—O1W | 2.208 (2) | | |
| | | |
O1—Zn1—O1W | 90.11 (9) | O1W—Zn1—N1 | 91.71 (9) |
O1—Zn1—N1 | 78.91 (10) | Zn1—O1—C10 | 115.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1A···O1i | 0.81 | 2.03 | 2.831 (3) | 169 |
O1W—H1B···O2Wii | 0.82 | 2.01 | 2.830 (4) | 172 |
O2W—H2A···O2 | 0.82 | 1.90 | 2.721 (4) | 175 |
O2W—H2B···O2Wiii | 0.82 | 2.17 | 2.944 (3) | 157 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2. |
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Isoquinoline-1-carboxylic acid (IQCA) inhibits the copper enzyme, dopamine β-hydroxylase (Townes et al., 1990). Up to this time, the crystal structure of the CuII (Tomas et al., 1999), SnIV (Smith et al., 1995), CoII and NiII complexes (Okabe & Muranishi, 2002) of IQCA have been reported clarifying the coordination modes of the complexes. In this study, we aimed to determine the structure of the ZnII complex (I), because ZnII has many important biological functions, for example, as a catalytic ion in many enzymes like the alcohol dehydrogenaze (Esposito et al., 2002), a zinc finger motif in a ribosomal protein (Dresios et al., 2002) or an insulin-mimetic complex in metallopharmaceutical compounds (Sakurai et al., 2002).
The molecular structure of (I) is shown in Fig. 1. The ZnII atom has a distorted octahedral coordination in the trans form defined by two N atoms and two O atoms of the two bidentate ligands in the equatorial plane, and two axial aqua O atoms. The coordination mode of (I) strongly resembles that of the CoII and NiII complexes (Okabe & Muranishi, 2002). The coordination bond length in the axial direction [Zn1—O1W 2.208 (2) Å] is longer than those in the equatorial plane (Table 1) which may be explained by a Jahn–Teller effect. The O—Zn—N chelate angle of the five-membered ring, 78.91 (10)°, is larger than in the CoII complex, 78.25 (7)°, but smaller than in both the NiII complex, 80.00 (9)° (Okabe & Muranishi, 2002), and the CuII complex, 82.96 (12)° for one of the two isoquinoline-1-carboxylate ligands and 83.15 (12)° for the second (Tomas, 1999)·The coordinated bond lengths of M—N are 2.096 (2) (CoII), 2.039 (3) (NiII), 2.084 (3) (ZnII), and 1.957 (3) and 1.969 (3) Å (CuII). These results indicate that the order of stability of these complexes corresponds to the well known Irving–Williams series, CoII < NiII < CuII > ZnII. In the crystal packing, the isoquinoline rings are stacked with respect to each other, with the mean distance of 3.392 (5) Å, in the similar manner to the CoII and NiII complexes (Okabe & Muranishi, 2002). Hydrogen bonds are formed between the coordinated water, the carboxylate group and the hydrated water molecules (Table 2).