metal-organic compounds
In the crystal structure of the title compound, [Zn (C12H8N2)(C3H5O5P)(H2O)2]·2H2O, the zinc atom is five-coordinate in a trigonal bipyramidal N2O3Zn environment; the apical sites are occupied by the aqua ligand and the N atom of the heterocycle. Hydrogen bonds link the zwitterions and lattice water molecules into a three-dimensional network motif.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013522/bt6468sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013522/bt6468Isup2.hkl |
CCDC reference: 245135
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Diaqua(1,10-Phenanthroline)[3-phosphonopropionato(2-)]zinc(II) dihydrate top
Crystal data top
[Zn(C12H8N2)(C3H5O5P)(H2O)2]·2H2O | F(000) = 1936 |
Mr = 469.68 | Dx = 1.626 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4886 reflections |
a = 24.991 (1) Å | θ = 2.4–27.0° |
b = 7.3516 (4) Å | µ = 1.42 mm−1 |
c = 20.958 (1) Å | T = 298 K |
β = 94.679 (1)° | Block, colorless |
V = 3837.5 (4) Å3 | 0.22 × 0.20 × 0.16 mm |
Z = 8 |
Data collection top
Bruker SMART APEX area-detector diffractometer | 4145 independent reflections |
Radiation source: fine-focus sealed tube | 3578 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −26→31 |
Tmin = 0.619, Tmax = 0.805 | k = −9→9 |
10830 measured reflections | l = −26→19 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0743P)2 + 3.8716P] where P = (Fo2 + 2Fc2)/3 |
4145 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.66 e Å−3 |
18 restraints | Δρmin = −0.69 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.382542 (12) | 0.34843 (4) | 0.593238 (14) | 0.03368 (13) | |
P1 | 0.30231 (3) | 0.67905 (9) | 0.58246 (3) | 0.03165 (17) | |
O1 | 0.35772 (8) | 0.5979 (3) | 0.58923 (10) | 0.0428 (5) | |
O2 | 0.26332 (9) | 0.5419 (3) | 0.54557 (10) | 0.0442 (5) | |
H2o | 0.2468 | 0.5941 | 0.5155 | 0.053* | |
O3 | 0.29988 (9) | 0.8627 (2) | 0.55044 (9) | 0.0404 (5) | |
O4 | 0.21483 (12) | 0.6892 (4) | 0.76772 (12) | 0.0727 (9) | |
O5 | 0.15461 (9) | 0.8771 (4) | 0.72059 (11) | 0.0562 (6) | |
O1w | 0.40134 (7) | 0.3550 (3) | 0.68779 (8) | 0.0354 (4) | |
H1w1 | 0.3774 | 0.3617 | 0.7134 | 0.042* | |
H1w2 | 0.4308 | 0.3257 | 0.7045 | 0.042* | |
O2w | 0.32455 (12) | 0.1687 (3) | 0.61263 (11) | 0.0648 (8) | |
H2w1 | 0.3124 | 0.0757 | 0.5920 | 0.078* | |
H2w2 | 0.3143 | 0.1680 | 0.6501 | 0.078* | |
O3w | 0.44738 (18) | 0.0441 (6) | 0.73618 (18) | 0.1215 (15) | |
H3w1 | 0.4316 | −0.0541 | 0.7181 | 0.146* | |
H3w2 | 0.4373 | 0.0531 | 0.7741 | 0.146* | |
O4w | 0.4460 (3) | −0.3234 (7) | 0.7351 (2) | 0.170 (3) | |
H4w1 | 0.4352 | −0.3673 | 0.6983 | 0.203* | |
H4w2 | 0.4268 | −0.3687 | 0.7636 | 0.203* | |
N1 | 0.46314 (10) | 0.3178 (3) | 0.57535 (11) | 0.0347 (5) | |
N2 | 0.37521 (9) | 0.2700 (3) | 0.49471 (10) | 0.0359 (5) | |
C1 | 0.47058 (10) | 0.2642 (3) | 0.51504 (12) | 0.0318 (5) | |
C2 | 0.50636 (13) | 0.3479 (4) | 0.61547 (14) | 0.0424 (7) | |
H2 | 0.5016 | 0.3847 | 0.6571 | 0.051* | |
C3 | 0.55831 (13) | 0.3268 (5) | 0.59765 (17) | 0.0497 (8) | |
H3 | 0.5875 | 0.3511 | 0.6268 | 0.060* | |
C4 | 0.56641 (12) | 0.2697 (4) | 0.53688 (15) | 0.0455 (7) | |
H4 | 0.6010 | 0.2530 | 0.5247 | 0.055* | |
C5 | 0.52171 (11) | 0.2370 (4) | 0.49334 (13) | 0.0367 (6) | |
C6 | 0.52558 (13) | 0.1782 (4) | 0.42859 (15) | 0.0453 (7) | |
H6 | 0.5593 | 0.1580 | 0.4141 | 0.054* | |
C7 | 0.48185 (14) | 0.1520 (4) | 0.38867 (15) | 0.0463 (7) | |
H7 | 0.4857 | 0.1126 | 0.3471 | 0.056* | |
C8 | 0.42906 (13) | 0.1831 (4) | 0.40838 (13) | 0.0388 (6) | |
C9 | 0.38151 (14) | 0.1673 (4) | 0.36790 (15) | 0.0491 (8) | |
H9 | 0.3831 | 0.1327 | 0.3254 | 0.059* | |
C10 | 0.33320 (14) | 0.2026 (5) | 0.39098 (15) | 0.0511 (8) | |
H10 | 0.3017 | 0.1932 | 0.3644 | 0.061* | |
C11 | 0.33148 (12) | 0.2533 (5) | 0.45515 (14) | 0.0441 (7) | |
H11 | 0.2983 | 0.2761 | 0.4706 | 0.053* | |
C12 | 0.42353 (11) | 0.2379 (3) | 0.47162 (12) | 0.0323 (5) | |
C13 | 0.27834 (12) | 0.6969 (4) | 0.66071 (14) | 0.0418 (6) | |
H13a | 0.2769 | 0.5764 | 0.6793 | 0.050* | |
H13b | 0.3035 | 0.7689 | 0.6878 | 0.050* | |
C14 | 0.22340 (12) | 0.7831 (5) | 0.65948 (14) | 0.0460 (7) | |
H14a | 0.2263 | 0.9094 | 0.6468 | 0.055* | |
H14b | 0.1999 | 0.7228 | 0.6269 | 0.055* | |
C15 | 0.19753 (12) | 0.7762 (5) | 0.72183 (13) | 0.0423 (6) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0381 (2) | 0.0340 (2) | 0.03029 (19) | −0.00138 (12) | 0.01077 (13) | −0.00422 (11) |
P1 | 0.0354 (4) | 0.0286 (3) | 0.0317 (4) | −0.0016 (3) | 0.0071 (3) | −0.0011 (2) |
O1 | 0.0353 (10) | 0.0359 (10) | 0.0587 (13) | −0.0012 (8) | 0.0120 (9) | −0.0069 (9) |
O2 | 0.0520 (12) | 0.0329 (10) | 0.0463 (12) | −0.0077 (9) | −0.0047 (9) | 0.0044 (8) |
O3 | 0.0553 (12) | 0.0295 (10) | 0.0357 (10) | −0.0069 (8) | 0.0008 (9) | −0.0003 (7) |
O4 | 0.0732 (17) | 0.101 (2) | 0.0481 (14) | 0.0399 (15) | 0.0303 (12) | 0.0314 (14) |
O5 | 0.0465 (12) | 0.0814 (17) | 0.0418 (12) | 0.0207 (11) | 0.0099 (10) | 0.0059 (11) |
O1w | 0.0321 (9) | 0.0556 (12) | 0.0195 (8) | −0.0040 (8) | 0.0081 (7) | 0.0015 (7) |
O2w | 0.102 (2) | 0.0515 (14) | 0.0452 (13) | −0.0404 (13) | 0.0325 (13) | −0.0182 (10) |
O3w | 0.155 (4) | 0.121 (3) | 0.092 (2) | 0.059 (3) | 0.028 (2) | 0.040 (2) |
O4w | 0.232 (5) | 0.172 (4) | 0.118 (3) | −0.137 (4) | 0.091 (3) | −0.081 (3) |
N1 | 0.0396 (12) | 0.0358 (12) | 0.0292 (11) | 0.0016 (9) | 0.0064 (9) | −0.0026 (9) |
N2 | 0.0380 (12) | 0.0377 (12) | 0.0333 (11) | −0.0019 (10) | 0.0101 (9) | −0.0047 (9) |
C1 | 0.0376 (13) | 0.0261 (12) | 0.0327 (13) | −0.0001 (10) | 0.0094 (10) | −0.0002 (10) |
C2 | 0.0454 (16) | 0.0465 (17) | 0.0353 (15) | 0.0006 (12) | 0.0031 (12) | −0.0038 (11) |
C3 | 0.0407 (16) | 0.059 (2) | 0.0488 (18) | −0.0026 (14) | −0.0030 (13) | 0.0018 (14) |
C4 | 0.0358 (14) | 0.0486 (17) | 0.0529 (18) | −0.0003 (13) | 0.0093 (12) | 0.0050 (14) |
C5 | 0.0387 (14) | 0.0318 (13) | 0.0412 (14) | −0.0016 (11) | 0.0128 (11) | 0.0029 (11) |
C6 | 0.0455 (17) | 0.0479 (17) | 0.0458 (17) | 0.0002 (13) | 0.0232 (14) | −0.0006 (13) |
C7 | 0.0575 (19) | 0.0492 (18) | 0.0350 (15) | −0.0027 (14) | 0.0208 (14) | −0.0053 (12) |
C8 | 0.0505 (16) | 0.0370 (14) | 0.0303 (13) | −0.0041 (12) | 0.0119 (12) | −0.0010 (11) |
C9 | 0.059 (2) | 0.059 (2) | 0.0298 (14) | −0.0106 (15) | 0.0075 (13) | −0.0081 (13) |
C10 | 0.0478 (17) | 0.064 (2) | 0.0406 (16) | −0.0105 (15) | −0.0007 (13) | −0.0080 (15) |
C11 | 0.0378 (14) | 0.0513 (17) | 0.0437 (16) | −0.0056 (13) | 0.0057 (12) | −0.0057 (13) |
C12 | 0.0403 (13) | 0.0280 (12) | 0.0297 (12) | −0.0022 (10) | 0.0100 (10) | −0.0008 (10) |
C13 | 0.0426 (15) | 0.0496 (16) | 0.0339 (14) | 0.0085 (13) | 0.0075 (11) | 0.0057 (12) |
C14 | 0.0466 (16) | 0.0593 (19) | 0.0334 (14) | 0.0121 (14) | 0.0113 (12) | 0.0083 (13) |
C15 | 0.0414 (15) | 0.0526 (17) | 0.0339 (14) | 0.0040 (13) | 0.0093 (11) | −0.0006 (13) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.935 (2) | C1—C12 | 1.440 (4) |
Zn1—O1w | 2.000 (2) | C2—C3 | 1.388 (5) |
Zn1—O2w | 2.027 (2) | C2—H2 | 0.9300 |
Zn1—N1 | 2.091 (2) | C3—C4 | 1.371 (5) |
Zn1—N2 | 2.137 (2) | C3—H3 | 0.9300 |
P1—O1 | 1.504 (2) | C4—C5 | 1.404 (4) |
P1—O3 | 1.5071 (19) | C4—H4 | 0.9300 |
P1—O2 | 1.562 (2) | C5—C6 | 1.435 (4) |
P1—C13 | 1.796 (3) | C6—C7 | 1.335 (5) |
O2—H2o | 0.8200 | C6—H6 | 0.9300 |
O4—C15 | 1.205 (4) | C7—C8 | 1.433 (4) |
O5—C15 | 1.303 (4) | C7—H7 | 0.9300 |
O1w—H1w1 | 0.84 | C8—C12 | 1.403 (4) |
O1w—H1w2 | 0.82 | C8—C9 | 1.407 (4) |
O2w—H2w1 | 0.85 | C9—C10 | 1.362 (5) |
O2w—H2w2 | 0.85 | C9—H9 | 0.9300 |
O3w—H3w1 | 0.89 | C10—C11 | 1.399 (4) |
O3w—H3w2 | 0.86 | C10—H10 | 0.9300 |
O4w—H4w1 | 0.86 | C11—H11 | 0.9300 |
O4w—H4w2 | 0.86 | C13—C14 | 1.510 (4) |
N1—C2 | 1.332 (4) | C13—H13a | 0.9700 |
N1—C1 | 1.351 (3) | C13—H13b | 0.9700 |
N2—C11 | 1.322 (4) | C14—C15 | 1.505 (4) |
N2—C12 | 1.358 (3) | C14—H14a | 0.9700 |
C1—C5 | 1.405 (4) | C14—H14b | 0.9700 |
O1—Zn1—O1w | 93.9 (1) | C3—C4—H4 | 120.5 |
O1—Zn1—O2w | 113.2 (1) | C5—C4—H4 | 120.5 |
O1—Zn1—N1 | 113.9 (1) | C1—C5—C4 | 117.5 (3) |
O1—Zn1—N2 | 102.2 (1) | C1—C5—C6 | 118.8 (3) |
O1w—Zn1—O2w | 86.0 (1) | C4—C5—C6 | 123.7 (3) |
O1w—Zn1—N1 | 91.6 (1) | C7—C6—C5 | 121.4 (3) |
O1w—Zn1—N2 | 163.5 (1) | C7—C6—H6 | 119.3 |
O2w—Zn1—N1 | 132.9 (1) | C5—C6—H6 | 119.3 |
O2w—Zn1—N2 | 90.7 (1) | C6—C7—C8 | 121.5 (3) |
N1—Zn1—N2 | 78.8 (1) | C6—C7—H7 | 119.3 |
O1—P1—O3 | 113.63 (13) | C8—C7—H7 | 119.3 |
O1—P1—O2 | 108.83 (12) | C12—C8—C9 | 116.7 (3) |
O3—P1—O2 | 110.92 (11) | C12—C8—C7 | 118.8 (3) |
O1—P1—C13 | 108.43 (13) | C9—C8—C7 | 124.4 (3) |
O3—P1—C13 | 109.67 (13) | C10—C9—C8 | 120.0 (3) |
O2—P1—C13 | 104.96 (14) | C10—C9—H9 | 120.0 |
P1—O1—Zn1 | 132.02 (13) | C8—C9—H9 | 120.0 |
P1—O2—H2o | 109.5 | C9—C10—C11 | 119.3 (3) |
Zn1—O1w—H1w1 | 121.0 | C9—C10—H10 | 120.3 |
Zn1—O1w—H1w2 | 123.3 | C11—C10—H10 | 120.3 |
H1w1—O1w—H1w2 | 113.9 | N2—C11—C10 | 122.6 (3) |
Zn1—O2w—H2w1 | 130.7 | N2—C11—H11 | 118.7 |
Zn1—O2w—H2w2 | 117.8 | C10—C11—H11 | 118.7 |
H2w1—O2w—H2w2 | 110.1 | N2—C12—C8 | 123.1 (3) |
H3w1—O3w—H3w2 | 107.8 | N2—C12—C1 | 117.1 (2) |
H4w1—O4w—H4w2 | 109.0 | C8—C12—C1 | 119.8 (2) |
C2—N1—C1 | 118.2 (2) | C14—C13—P1 | 112.7 (2) |
C2—N1—Zn1 | 127.8 (2) | C14—C13—H13a | 109.1 |
C1—N1—Zn1 | 114.04 (18) | P1—C13—H13a | 109.1 |
C11—N2—C12 | 118.3 (2) | C14—C13—H13b | 109.1 |
C11—N2—Zn1 | 129.21 (19) | P1—C13—H13b | 109.1 |
C12—N2—Zn1 | 112.49 (17) | H13a—C13—H13b | 107.8 |
N1—C1—C5 | 122.8 (2) | C15—C14—C13 | 115.2 (2) |
N1—C1—C12 | 117.6 (2) | C15—C14—H14a | 108.5 |
C5—C1—C12 | 119.6 (2) | C13—C14—H14a | 108.5 |
N1—C2—C3 | 122.6 (3) | C15—C14—H14b | 108.5 |
N1—C2—H2 | 118.7 | C13—C14—H14b | 108.5 |
C3—C2—H2 | 118.7 | H14a—C14—H14b | 107.5 |
C4—C3—C2 | 119.7 (3) | O4—C15—O5 | 124.0 (3) |
C4—C3—H3 | 120.1 | O4—C15—C14 | 124.0 (3) |
C2—C3—H3 | 120.1 | O5—C15—C14 | 112.0 (3) |
C3—C4—C5 | 119.1 (3) | ||
O3—P1—O1—Zn1 | −152.04 (15) | N1—C1—C5—C6 | 179.4 (2) |
O2—P1—O1—Zn1 | −27.9 (2) | C12—C1—C5—C6 | −1.8 (4) |
C13—P1—O1—Zn1 | 85.7 (2) | C3—C4—C5—C1 | −0.3 (4) |
O1w—Zn1—O1—P1 | −103.89 (18) | C3—C4—C5—C6 | 179.6 (3) |
O2w—Zn1—O1—P1 | −16.5 (2) | C1—C5—C6—C7 | 1.1 (4) |
N1—Zn1—O1—P1 | 162.58 (16) | C4—C5—C6—C7 | −178.8 (3) |
N2—Zn1—O1—P1 | 79.56 (18) | C5—C6—C7—C8 | 0.7 (5) |
O1—Zn1—N1—C2 | 79.0 (3) | C6—C7—C8—C12 | −1.6 (4) |
O1w—Zn1—N1—C2 | −16.0 (2) | C6—C7—C8—C9 | 176.5 (3) |
O2w—Zn1—N1—C2 | −102.1 (3) | C12—C8—C9—C10 | −0.7 (5) |
N2—Zn1—N1—C2 | 177.6 (3) | C7—C8—C9—C10 | −178.9 (3) |
O1—Zn1—N1—C1 | −99.58 (19) | C8—C9—C10—C11 | −0.4 (5) |
O1w—Zn1—N1—C1 | 165.39 (18) | C12—N2—C11—C10 | 0.6 (5) |
O2w—Zn1—N1—C1 | 79.3 (2) | Zn1—N2—C11—C10 | 179.0 (2) |
N2—Zn1—N1—C1 | −1.04 (18) | C9—C10—C11—N2 | 0.6 (5) |
O1—Zn1—N2—C11 | −65.1 (3) | C11—N2—C12—C8 | −1.8 (4) |
O1w—Zn1—N2—C11 | 127.1 (3) | Zn1—N2—C12—C8 | 179.4 (2) |
O2w—Zn1—N2—C11 | 48.8 (3) | C11—N2—C12—C1 | 177.6 (3) |
N1—Zn1—N2—C11 | −177.4 (3) | Zn1—N2—C12—C1 | −1.2 (3) |
O1—Zn1—N2—C12 | 113.43 (19) | C9—C8—C12—N2 | 1.9 (4) |
O1w—Zn1—N2—C12 | −54.4 (4) | C7—C8—C12—N2 | −179.8 (3) |
O2w—Zn1—N2—C12 | −132.6 (2) | C9—C8—C12—C1 | −177.5 (3) |
N1—Zn1—N2—C12 | 1.18 (18) | C7—C8—C12—C1 | 0.8 (4) |
C2—N1—C1—C5 | 0.8 (4) | N1—C1—C12—N2 | 0.3 (4) |
Zn1—N1—C1—C5 | 179.6 (2) | C5—C1—C12—N2 | −178.6 (2) |
C2—N1—C1—C12 | −178.0 (2) | N1—C1—C12—C8 | 179.7 (2) |
Zn1—N1—C1—C12 | 0.8 (3) | C5—C1—C12—C8 | 0.9 (4) |
C1—N1—C2—C3 | 0.1 (4) | O1—P1—C13—C14 | 178.1 (2) |
Zn1—N1—C2—C3 | −178.5 (2) | O3—P1—C13—C14 | 53.5 (3) |
N1—C2—C3—C4 | −1.1 (5) | O2—P1—C13—C14 | −65.7 (3) |
C2—C3—C4—C5 | 1.2 (5) | P1—C13—C14—C15 | 171.1 (2) |
N1—C1—C5—C4 | −0.7 (4) | C13—C14—C15—O4 | −9.5 (5) |
C12—C1—C5—C4 | 178.1 (2) | C13—C14—C15—O5 | 169.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O3i | 0.82 | 1.76 | 2.553 (3) | 161 |
O1w—H1w1···O5ii | 0.84 | 1.66 | 2.471 (3) | 163 |
O1w—H1w2···O3w | 0.82 | 2.20 | 2.718 (4) | 121 |
O2w—H2w1···O3iii | 0.85 | 1.81 | 2.647 (3) | 169 |
O2w—H2w2···O4ii | 0.85 | 1.93 | 2.772 (3) | 173 |
O3w—H3w1···O4w | 0.89 | 2.04 | 2.702 (8) | 130 |
O4w—H4w1···O1wiii | 0.86 | 2.21 | 2.764 (4) | 122 |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x, y−1, z. |