In the centrosymmetric title compound, [Zn
2(C
7H
3NO
4)
2(C
10H
8N
2)(H
2O)
6]·2H
2O, each Zn
II atom is six-coordinated in an octahedral geometry by one N atom of 4,4′-bipyridine (bpy), one N atom and one O atom of pyridine-2,4-dicarboxylate (pydc) and three water molecules. The crystal structure features O—H
O hydrogen bonds between carboxylate groups and water molecules, and π–π stacking interactions between the bpy and pydc molecules.
Supporting information
CCDC reference: 636696
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.061
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.36
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
µ-4,4'-Bipyridine-
κ2N:
N'-bis[triaqua(pyridine-2,4-dicarboxylato-
κ2N,
O2)zinc(II)] dihydrate
top
Crystal data top
[Zn2(C7H3NO4)2(C10H8N2)(H2O)6]·2H2O | F(000) = 780 |
Mr = 761.26 | Dx = 1.679 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2663 reflections |
a = 10.023 (2) Å | θ = 2.1–26.1° |
b = 13.941 (3) Å | µ = 1.68 mm−1 |
c = 11.239 (2) Å | T = 292 K |
β = 106.478 (3)° | Needle, colorless |
V = 1505.9 (5) Å3 | 0.43 × 0.07 × 0.06 mm |
Z = 2 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 2985 independent reflections |
Radiation source: fine-focus sealed tube | 1979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ and ω scans | θmax = 26.1°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.860, Tmax = 0.899 | k = −16→17 |
8056 measured reflections | l = −6→13 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 0.83 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
2985 reflections | (Δ/σ)max = 0.001 |
216 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.57152 (4) | 0.91603 (3) | 0.21486 (3) | 0.02243 (11) | |
O1 | 0.5776 (2) | 0.86948 (15) | 0.03684 (17) | 0.0254 (5) | |
O5 | 0.5137 (2) | 0.77228 (15) | 0.25046 (19) | 0.0265 (5) | |
N2 | 0.3530 (2) | 0.94228 (18) | 0.1478 (2) | 0.0239 (6) | |
O7 | 0.6063 (2) | 0.95211 (16) | 0.40266 (18) | 0.0300 (6) | |
C10 | 0.0733 (3) | 0.9875 (2) | 0.0330 (3) | 0.0230 (8) | |
O6 | 0.6009 (2) | 1.06096 (15) | 0.1887 (2) | 0.0330 (6) | |
N1 | 0.7846 (2) | 0.87347 (18) | 0.2489 (2) | 0.0222 (6) | |
C2 | 0.8071 (3) | 0.8276 (2) | 0.1523 (3) | 0.0210 (7) | |
O2 | 0.7079 (2) | 0.78200 (18) | −0.0542 (2) | 0.0429 (7) | |
C3 | 0.9321 (3) | 0.7842 (2) | 0.1574 (3) | 0.0256 (8) | |
H1 | 0.9424 | 0.7492 | 0.0901 | 0.031* | |
C11 | 0.1413 (3) | 0.9155 (3) | −0.0100 (3) | 0.0366 (9) | |
H5 | 0.0945 | 0.8810 | −0.0803 | 0.044* | |
C1 | 0.6868 (3) | 0.8255 (2) | 0.0348 (3) | 0.0255 (8) | |
C6 | 0.8902 (3) | 0.8810 (2) | 0.3525 (3) | 0.0315 (9) | |
H2 | 0.8752 | 0.9127 | 0.4204 | 0.038* | |
C5 | 1.0203 (3) | 0.8437 (2) | 0.3628 (3) | 0.0298 (9) | |
H3 | 1.0922 | 0.8522 | 0.4353 | 0.036* | |
C12 | 0.2775 (3) | 0.8940 (2) | 0.0498 (3) | 0.0334 (9) | |
H4 | 0.3191 | 0.8432 | 0.0203 | 0.040* | |
C8 | 0.2870 (3) | 1.0110 (3) | 0.1908 (3) | 0.0416 (10) | |
H7 | 0.3363 | 1.0446 | 0.2610 | 0.050* | |
C9 | 0.1501 (3) | 1.0348 (3) | 0.1373 (3) | 0.0462 (11) | |
H6 | 0.1092 | 1.0832 | 0.1719 | 0.055* | |
C4 | 1.0427 (3) | 0.7934 (2) | 0.2642 (3) | 0.0220 (7) | |
O4 | 1.2882 (2) | 0.78230 (17) | 0.34266 (19) | 0.0357 (6) | |
O3 | 1.1781 (2) | 0.67490 (18) | 0.2021 (2) | 0.0464 (7) | |
C7 | 1.1811 (3) | 0.7459 (3) | 0.2688 (3) | 0.0272 (8) | |
H13 | 0.4399 | 0.7670 | 0.2689 | 0.055 (13)* | |
H11 | 0.5572 | 1.0878 | 0.1300 | 0.034 (11)* | |
H12 | 0.5709 | 0.7486 | 0.3077 | 0.044 (12)* | |
H10 | 0.6831 | 1.0997 | 0.2316 | 0.086 (14)* | |
H9 | 0.5931 | 1.0197 | 0.4273 | 0.063 (12)* | |
H8 | 0.5792 | 0.9138 | 0.4586 | 0.087 (15)* | |
O8 | 0.4555 (2) | 0.63637 (16) | 0.0482 (3) | 0.0378 (6) | |
H2W | 0.3947 | 0.6604 | −0.0256 | 0.106 (18)* | |
H1W | 0.4748 | 0.6675 | 0.1025 | 0.051 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0149 (2) | 0.0250 (2) | 0.0264 (2) | 0.00229 (18) | 0.00444 (14) | −0.00003 (18) |
O1 | 0.0136 (12) | 0.0373 (15) | 0.0240 (13) | 0.0050 (10) | 0.0030 (9) | 0.0024 (10) |
O5 | 0.0159 (13) | 0.0331 (15) | 0.0297 (13) | 0.0013 (10) | 0.0051 (11) | 0.0053 (11) |
N2 | 0.0133 (14) | 0.0244 (17) | 0.0307 (16) | 0.0025 (12) | 0.0009 (12) | 0.0001 (12) |
O7 | 0.0371 (15) | 0.0307 (15) | 0.0247 (13) | 0.0026 (11) | 0.0127 (11) | −0.0011 (11) |
C10 | 0.0137 (18) | 0.025 (2) | 0.030 (2) | 0.0012 (15) | 0.0059 (15) | 0.0006 (15) |
O6 | 0.0281 (14) | 0.0271 (15) | 0.0360 (14) | −0.0051 (11) | −0.0036 (11) | 0.0069 (12) |
N1 | 0.0155 (15) | 0.0280 (17) | 0.0218 (16) | 0.0022 (12) | 0.0033 (12) | −0.0025 (12) |
C2 | 0.0142 (17) | 0.023 (2) | 0.0254 (19) | 0.0001 (14) | 0.0053 (14) | −0.0022 (14) |
O2 | 0.0228 (14) | 0.070 (2) | 0.0317 (15) | 0.0087 (12) | 0.0010 (11) | −0.0207 (13) |
C3 | 0.0194 (19) | 0.031 (2) | 0.0252 (19) | 0.0025 (15) | 0.0043 (15) | −0.0055 (15) |
C11 | 0.0206 (19) | 0.047 (2) | 0.036 (2) | 0.0072 (18) | −0.0017 (15) | −0.0159 (18) |
C1 | 0.0184 (19) | 0.032 (2) | 0.024 (2) | −0.0014 (16) | 0.0022 (15) | −0.0020 (16) |
C6 | 0.025 (2) | 0.045 (2) | 0.024 (2) | 0.0071 (17) | 0.0056 (15) | −0.0042 (16) |
C5 | 0.020 (2) | 0.039 (2) | 0.024 (2) | 0.0035 (16) | −0.0045 (15) | −0.0032 (16) |
C12 | 0.0208 (19) | 0.037 (2) | 0.040 (2) | 0.0077 (16) | 0.0050 (16) | −0.0112 (17) |
C8 | 0.025 (2) | 0.046 (3) | 0.045 (2) | 0.0077 (18) | −0.0050 (17) | −0.0220 (19) |
C9 | 0.024 (2) | 0.053 (3) | 0.053 (3) | 0.0164 (19) | −0.0028 (18) | −0.026 (2) |
C4 | 0.0144 (17) | 0.027 (2) | 0.0230 (18) | 0.0006 (14) | 0.0027 (14) | 0.0026 (14) |
O4 | 0.0149 (13) | 0.0520 (17) | 0.0373 (15) | 0.0025 (11) | 0.0024 (10) | −0.0055 (12) |
O3 | 0.0268 (15) | 0.054 (2) | 0.0508 (17) | 0.0165 (13) | −0.0013 (12) | −0.0168 (13) |
C7 | 0.021 (2) | 0.038 (2) | 0.022 (2) | 0.0072 (17) | 0.0050 (15) | 0.0086 (17) |
O8 | 0.0523 (18) | 0.0329 (15) | 0.0288 (15) | 0.0042 (12) | 0.0126 (12) | 0.0008 (14) |
Geometric parameters (Å, º) top
Zn1—O6 | 2.075 (2) | C2—C3 | 1.378 (4) |
Zn1—O7 | 2.101 (2) | C2—C1 | 1.515 (4) |
Zn1—O1 | 2.121 (2) | O2—C1 | 1.237 (3) |
Zn1—N2 | 2.136 (2) | C3—C4 | 1.389 (4) |
Zn1—N1 | 2.143 (2) | C3—H1 | 0.9300 |
Zn1—O5 | 2.155 (2) | C11—C12 | 1.373 (4) |
O1—C1 | 1.261 (3) | C11—H5 | 0.9300 |
O5—H13 | 0.83 | C6—C5 | 1.378 (4) |
O5—H12 | 0.80 | C6—H2 | 0.9300 |
N2—C12 | 1.328 (4) | C5—C4 | 1.384 (4) |
N2—C8 | 1.330 (4) | C5—H3 | 0.9300 |
O7—H9 | 1.00 | C12—H4 | 0.9300 |
O7—H8 | 0.92 | C8—C9 | 1.374 (4) |
C10—C9 | 1.375 (4) | C8—H7 | 0.9300 |
C10—C11 | 1.376 (4) | C9—H6 | 0.9300 |
C10—C10i | 1.488 (5) | C4—C7 | 1.524 (4) |
O6—H11 | 0.78 | O4—C7 | 1.262 (3) |
O6—H10 | 0.99 | O3—C7 | 1.238 (4) |
N1—C2 | 1.334 (3) | O8—H2W | 0.94 |
N1—C6 | 1.337 (3) | O8—H1W | 0.73 |
| | | |
O6—Zn1—O7 | 85.38 (9) | N1—C2—C3 | 122.6 (3) |
O6—Zn1—O1 | 96.95 (8) | N1—C2—C1 | 116.3 (3) |
O7—Zn1—O1 | 168.62 (8) | C3—C2—C1 | 121.2 (3) |
O6—Zn1—N2 | 87.45 (9) | C2—C3—C4 | 119.3 (3) |
O7—Zn1—N2 | 100.08 (9) | C2—C3—H1 | 120.3 |
O1—Zn1—N2 | 91.17 (9) | C4—C3—H1 | 120.3 |
O6—Zn1—N1 | 96.94 (9) | C12—C11—C10 | 120.6 (3) |
O7—Zn1—N1 | 90.78 (9) | C12—C11—H5 | 119.7 |
O1—Zn1—N1 | 77.88 (8) | C10—C11—H5 | 119.7 |
N2—Zn1—N1 | 168.60 (9) | O2—C1—O1 | 127.0 (3) |
O6—Zn1—O5 | 171.28 (9) | O2—C1—C2 | 116.0 (3) |
O7—Zn1—O5 | 90.74 (8) | O1—C1—C2 | 117.0 (3) |
O1—Zn1—O5 | 88.39 (8) | N1—C6—C5 | 122.7 (3) |
N2—Zn1—O5 | 85.54 (9) | N1—C6—H2 | 118.7 |
N1—Zn1—O5 | 90.92 (9) | C5—C6—H2 | 118.7 |
C1—O1—Zn1 | 115.08 (19) | C6—C5—C4 | 119.3 (3) |
Zn1—O5—H13 | 115.8 | C6—C5—H3 | 120.4 |
Zn1—O5—H12 | 111.3 | C4—C5—H3 | 120.4 |
H13—O5—H12 | 104.5 | N2—C12—C11 | 123.3 (3) |
C12—N2—C8 | 116.2 (3) | N2—C12—H4 | 118.3 |
C12—N2—Zn1 | 119.5 (2) | C11—C12—H4 | 118.3 |
C8—N2—Zn1 | 124.1 (2) | N2—C8—C9 | 123.6 (3) |
Zn1—O7—H9 | 120.4 | N2—C8—H7 | 118.2 |
Zn1—O7—H8 | 123.3 | C9—C8—H7 | 118.2 |
H9—O7—H8 | 105.6 | C8—C9—C10 | 120.3 (3) |
C9—C10—C11 | 115.9 (3) | C8—C9—H6 | 119.8 |
C9—C10—C10i | 123.2 (4) | C10—C9—H6 | 119.8 |
C11—C10—C10i | 120.9 (3) | C5—C4—C3 | 117.9 (3) |
Zn1—O6—H11 | 121.5 | C5—C4—C7 | 123.1 (3) |
Zn1—O6—H10 | 126.5 | C3—C4—C7 | 119.0 (3) |
H11—O6—H10 | 110.0 | O3—C7—O4 | 126.1 (3) |
C2—N1—C6 | 118.1 (3) | O3—C7—C4 | 117.5 (3) |
C2—N1—Zn1 | 112.17 (19) | O4—C7—C4 | 116.4 (3) |
C6—N1—Zn1 | 129.5 (2) | H2W—O8—H1W | 118.6 |
| | | |
O6—Zn1—O1—C1 | 106.9 (2) | N1—C2—C3—C4 | −4.3 (5) |
O7—Zn1—O1—C1 | 5.7 (6) | C1—C2—C3—C4 | 175.7 (3) |
N2—Zn1—O1—C1 | −165.5 (2) | C9—C10—C11—C12 | 0.0 (5) |
N1—Zn1—O1—C1 | 11.3 (2) | C10i—C10—C11—C12 | 178.7 (4) |
O5—Zn1—O1—C1 | −80.0 (2) | Zn1—O1—C1—O2 | 170.8 (3) |
O6—Zn1—N2—C12 | 122.5 (2) | Zn1—O1—C1—C2 | −10.8 (4) |
O7—Zn1—N2—C12 | −152.6 (2) | N1—C2—C1—O2 | −179.3 (3) |
O1—Zn1—N2—C12 | 25.6 (2) | C3—C2—C1—O2 | 0.7 (5) |
N1—Zn1—N2—C12 | 9.5 (6) | N1—C2—C1—O1 | 2.1 (4) |
O5—Zn1—N2—C12 | −62.7 (2) | C3—C2—C1—O1 | −177.8 (3) |
O6—Zn1—N2—C8 | −51.1 (3) | C2—N1—C6—C5 | 0.2 (5) |
O7—Zn1—N2—C8 | 33.7 (3) | Zn1—N1—C6—C5 | 175.1 (2) |
O1—Zn1—N2—C8 | −148.0 (3) | N1—C6—C5—C4 | −2.3 (5) |
N1—Zn1—N2—C8 | −164.1 (4) | C8—N2—C12—C11 | 3.6 (5) |
O5—Zn1—N2—C8 | 123.7 (3) | Zn1—N2—C12—C11 | −170.6 (3) |
O6—Zn1—N1—C2 | −105.3 (2) | C10—C11—C12—N2 | −2.6 (6) |
O7—Zn1—N1—C2 | 169.3 (2) | C12—N2—C8—C9 | −2.0 (5) |
O1—Zn1—N1—C2 | −9.6 (2) | Zn1—N2—C8—C9 | 171.8 (3) |
N2—Zn1—N1—C2 | 6.8 (6) | N2—C8—C9—C10 | −0.5 (6) |
O5—Zn1—N1—C2 | 78.5 (2) | C11—C10—C9—C8 | 1.5 (5) |
O6—Zn1—N1—C6 | 79.6 (3) | C10i—C10—C9—C8 | −177.2 (4) |
O7—Zn1—N1—C6 | −5.9 (3) | C6—C5—C4—C3 | 1.1 (5) |
O1—Zn1—N1—C6 | 175.2 (3) | C6—C5—C4—C7 | −177.3 (3) |
N2—Zn1—N1—C6 | −168.3 (4) | C2—C3—C4—C5 | 2.0 (5) |
O5—Zn1—N1—C6 | −96.6 (3) | C2—C3—C4—C7 | −179.5 (3) |
C6—N1—C2—C3 | 3.1 (5) | C5—C4—C7—O3 | 152.3 (3) |
Zn1—N1—C2—C3 | −172.6 (2) | C3—C4—C7—O3 | −26.0 (5) |
C6—N1—C2—C1 | −176.8 (3) | C5—C4—C7—O4 | −26.5 (5) |
Zn1—N1—C2—C1 | 7.4 (3) | C3—C4—C7—O4 | 155.1 (3) |
Symmetry code: (i) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H12···O2ii | 0.80 | 1.81 | 2.599 (3) | 169 |
O5—H13···O4iii | 0.83 | 1.94 | 2.744 (3) | 165 |
O6—H11···O1iv | 0.78 | 2.06 | 2.827 (3) | 168 |
O6—H10···O3v | 0.99 | 1.73 | 2.719 (3) | 175 |
O7—H8···O8ii | 0.92 | 1.94 | 2.808 (3) | 157 |
O7—H9···O8vi | 1.00 | 1.74 | 2.735 (3) | 171 |
O8—H1W···O5 | 0.73 | 2.17 | 2.889 (4) | 173 |
O8—H2W···O4vii | 0.94 | 1.75 | 2.689 (4) | 174 |
Symmetry codes: (ii) x, −y+3/2, z+1/2; (iii) x−1, y, z; (iv) −x+1, −y+2, −z; (v) −x+2, y+1/2, −z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) x−1, −y+3/2, z−1/2. |