metal-organic compounds
catena-Poly[[chlorido[1-(3-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone-κC2]mercury(II)]-μ-chlorido]
aDepartment of Chemistry, Faculty of Science, Urmia University, PO Box 57153-165, Urmia, Iran, and bDepartment of Chemistry, Missouri University of Science and Technology, Rolla, MO 65409, USA
*Correspondence e-mail: dadrassi@yahoo.com
In the title organometallic polymer, [HgCl2(C26H20NO3P)]n, the monodentate 1-(3-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone ligand is coordinated to the HgII atom through the methine C atom. The HgII atom is four-coordinated in a distorted tetrahedral geometry by one terminal Cl atom, two bridging Cl atoms, and one C atom from the ylidic ligand, resulting in a polymeric chain parallel to [010]. The terminal Cl atom is more strongly bound to the HgII ion [2.3916 (9) Å] than the bridging Cl atoms. The bridge is asymmetric, as indicated by the two different Hg—Cl(bridging) bond lengths [2.5840 (8) and 2.7876 (8) Å]. Intramolecular C—H⋯O and weak C—H⋯Cl contacts stabilize the polymeric chain. In the crystal, adjacent chains interact via C—H⋯O hydrogen bonds.
Related literature
For an example of a one-dimensional polymeric HgII complex, see: Ebrahim et al. (2007). For mono- and dimeric complexes of HgII containing ylide ligands, see: Sabounchei et al. (2007, 2008, 2009, 2011); Sabounchei, Jodaian et al. (2010); Sabounchei, Samiee et al. (2010).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812043073/bh2457sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812043073/bh2457Isup2.hkl
All reagents and solvents employed were commercially available and were used as received without further purification. The ligand 1-(3-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone (0.637 g, 1.5 mmol) in methanol (10 ml) was added dropwise to HgCl2 (0.407 g, 1.5 mmol) in the same solvent (10 ml). After standing for 15 h without stirring at room temperature, colourless crystals of the title complex were obtained. Yield: 62%.
H atoms were positioned geometrically with C—H = 0.93 Å (aromatic) or 0.98 Å (methine) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(carrier C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[HgCl2(C26H20NO3P)] | F(000) = 1344 |
Mr = 696.89 | Dx = 1.864 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1017 reflections |
a = 12.589 (3) Å | θ = 3.0–27.4° |
b = 8.1026 (17) Å | µ = 6.51 mm−1 |
c = 25.231 (6) Å | T = 293 K |
β = 105.174 (2)° | Prism, colourless |
V = 2483.8 (9) Å3 | 0.61 × 0.15 × 0.12 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 6143 independent reflections |
Radiation source: fine-focus sealed tube | 5049 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −16→16 |
Tmin = 0.109, Tmax = 0.499 | k = −10→10 |
29804 measured reflections | l = −33→33 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.6725P] where P = (Fo2 + 2Fc2)/3 |
6143 reflections | (Δ/σ)max = 0.002 |
307 parameters | Δρmax = 0.96 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
0 constraints |
[HgCl2(C26H20NO3P)] | V = 2483.8 (9) Å3 |
Mr = 696.89 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.589 (3) Å | µ = 6.51 mm−1 |
b = 8.1026 (17) Å | T = 293 K |
c = 25.231 (6) Å | 0.61 × 0.15 × 0.12 mm |
β = 105.174 (2)° |
Bruker SMART APEX CCD area-detector diffractometer | 6143 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5049 reflections with I > 2σ(I) |
Tmin = 0.109, Tmax = 0.499 | Rint = 0.034 |
29804 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.96 e Å−3 |
6143 reflections | Δρmin = −0.45 e Å−3 |
307 parameters |
x | y | z | Uiso*/Ueq | ||
Hg1 | 0.394304 (9) | 0.004646 (12) | 0.767518 (5) | 0.04050 (5) | |
Cl1 | 0.48115 (6) | −0.31360 (8) | 0.77525 (3) | 0.04764 (18) | |
Cl2 | 0.22022 (7) | −0.03302 (11) | 0.70223 (4) | 0.0586 (2) | |
P1 | 0.33345 (5) | 0.13556 (8) | 0.87895 (3) | 0.02688 (13) | |
C1 | 0.6575 (2) | 0.0932 (3) | 0.87894 (10) | 0.0329 (6) | |
C2 | 0.7437 (2) | 0.2055 (4) | 0.89500 (11) | 0.0382 (6) | |
H2A | 0.7295 | 0.3174 | 0.8977 | 0.046* | |
C3 | 0.8496 (2) | 0.1491 (5) | 0.90675 (12) | 0.0481 (8) | |
C4 | 0.8745 (3) | −0.0152 (5) | 0.90283 (18) | 0.0634 (11) | |
H4A | 0.9473 | −0.0502 | 0.9108 | 0.076* | |
C5 | 0.7897 (3) | −0.1265 (5) | 0.88698 (16) | 0.0644 (10) | |
H5A | 0.8050 | −0.2379 | 0.8841 | 0.077* | |
C6 | 0.6810 (2) | −0.0729 (4) | 0.87524 (13) | 0.0474 (7) | |
H6A | 0.6239 | −0.1487 | 0.8649 | 0.057* | |
C7 | 0.54244 (19) | 0.1632 (3) | 0.86703 (10) | 0.0289 (5) | |
N1 | 0.9400 (2) | 0.2703 (5) | 0.92431 (12) | 0.0708 (10) | |
O1 | 0.9181 (2) | 0.4070 (5) | 0.93769 (13) | 0.0896 (9) | |
O2 | 1.0322 (2) | 0.2238 (5) | 0.92538 (17) | 0.1280 (14) | |
O3 | 0.53055 (15) | 0.3129 (2) | 0.86724 (8) | 0.0414 (4) | |
C8 | 0.4477 (2) | 0.0510 (3) | 0.85832 (11) | 0.0306 (5) | |
H8A | 0.4705 | −0.0531 | 0.8777 | 0.037* | |
C9 | 0.24626 (19) | 0.2639 (3) | 0.82721 (10) | 0.0293 (5) | |
C10 | 0.2909 (2) | 0.3735 (3) | 0.79627 (11) | 0.0387 (6) | |
H10A | 0.3668 | 0.3864 | 0.8039 | 0.046* | |
C11 | 0.2228 (3) | 0.4628 (4) | 0.75433 (14) | 0.0481 (8) | |
H11A | 0.2530 | 0.5347 | 0.7335 | 0.058* | |
C12 | 0.1103 (3) | 0.4461 (5) | 0.74316 (14) | 0.0510 (8) | |
H12A | 0.0648 | 0.5048 | 0.7143 | 0.061* | |
C13 | 0.0650 (2) | 0.3422 (4) | 0.77476 (13) | 0.0502 (8) | |
H13A | −0.0111 | 0.3340 | 0.7678 | 0.060* | |
C14 | 0.1319 (2) | 0.2502 (4) | 0.81666 (12) | 0.0406 (6) | |
H14A | 0.1010 | 0.1798 | 0.8376 | 0.049* | |
C15 | 0.2511 (2) | −0.0368 (3) | 0.89107 (11) | 0.0301 (5) | |
C16 | 0.2028 (3) | −0.1434 (4) | 0.84876 (12) | 0.0525 (8) | |
H16A | 0.2127 | −0.1269 | 0.8139 | 0.063* | |
C17 | 0.1398 (3) | −0.2744 (4) | 0.85828 (14) | 0.0594 (9) | |
H17A | 0.1082 | −0.3461 | 0.8297 | 0.071* | |
C18 | 0.1233 (2) | −0.2999 (4) | 0.90891 (13) | 0.0476 (7) | |
H18A | 0.0806 | −0.3880 | 0.9150 | 0.057* | |
C19 | 0.1707 (3) | −0.1941 (4) | 0.95080 (13) | 0.0527 (8) | |
H19A | 0.1596 | −0.2107 | 0.9854 | 0.063* | |
C20 | 0.2344 (2) | −0.0633 (4) | 0.94231 (12) | 0.0428 (6) | |
H20A | 0.2661 | 0.0072 | 0.9712 | 0.051* | |
C21 | 0.37502 (19) | 0.2448 (3) | 0.94318 (10) | 0.0307 (5) | |
C22 | 0.2989 (2) | 0.3465 (3) | 0.95842 (12) | 0.0449 (7) | |
H22A | 0.2315 | 0.3684 | 0.9337 | 0.054* | |
C23 | 0.3237 (3) | 0.4147 (4) | 1.01033 (13) | 0.0549 (8) | |
H23A | 0.2719 | 0.4803 | 1.0206 | 0.066* | |
C24 | 0.4236 (3) | 0.3871 (4) | 1.04692 (12) | 0.0501 (8) | |
H24A | 0.4398 | 0.4347 | 1.0817 | 0.060* | |
C25 | 0.4997 (3) | 0.2890 (4) | 1.03198 (11) | 0.0438 (7) | |
H25A | 0.5680 | 0.2715 | 1.0566 | 0.053* | |
C26 | 0.4759 (2) | 0.2155 (3) | 0.98068 (12) | 0.0358 (6) | |
H26A | 0.5273 | 0.1467 | 0.9713 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.04069 (8) | 0.04342 (8) | 0.03615 (8) | −0.00409 (4) | 0.00785 (5) | −0.00748 (4) |
Cl1 | 0.0525 (4) | 0.0346 (3) | 0.0604 (5) | 0.0059 (3) | 0.0229 (4) | −0.0059 (3) |
Cl2 | 0.0417 (4) | 0.0791 (6) | 0.0487 (5) | −0.0070 (4) | 0.0004 (4) | −0.0165 (4) |
P1 | 0.0237 (3) | 0.0288 (3) | 0.0275 (3) | −0.0013 (2) | 0.0054 (2) | −0.0014 (2) |
C1 | 0.0253 (12) | 0.0462 (15) | 0.0272 (13) | 0.0017 (11) | 0.0069 (10) | 0.0012 (11) |
C2 | 0.0293 (13) | 0.0553 (17) | 0.0315 (14) | −0.0073 (12) | 0.0108 (11) | −0.0036 (12) |
C3 | 0.0293 (15) | 0.082 (2) | 0.0348 (16) | −0.0070 (15) | 0.0119 (12) | −0.0037 (15) |
C4 | 0.0338 (18) | 0.095 (3) | 0.061 (2) | 0.0151 (17) | 0.0117 (17) | −0.0031 (18) |
C5 | 0.046 (2) | 0.068 (2) | 0.077 (3) | 0.0197 (18) | 0.0127 (18) | −0.0060 (19) |
C6 | 0.0343 (16) | 0.0497 (18) | 0.056 (2) | 0.0063 (13) | 0.0084 (14) | −0.0019 (15) |
C7 | 0.0246 (12) | 0.0341 (13) | 0.0283 (12) | 0.0001 (10) | 0.0076 (10) | −0.0031 (10) |
N1 | 0.0300 (15) | 0.130 (3) | 0.0531 (18) | −0.0224 (18) | 0.0115 (13) | −0.0100 (19) |
O1 | 0.0589 (18) | 0.114 (3) | 0.094 (2) | −0.0417 (19) | 0.0161 (15) | −0.026 (2) |
O2 | 0.0335 (15) | 0.190 (4) | 0.165 (3) | −0.0242 (19) | 0.0340 (18) | −0.030 (3) |
O3 | 0.0337 (10) | 0.0352 (10) | 0.0523 (12) | −0.0018 (8) | 0.0060 (9) | −0.0041 (9) |
C8 | 0.0257 (12) | 0.0305 (11) | 0.0341 (14) | 0.0010 (10) | 0.0053 (10) | −0.0003 (11) |
C9 | 0.0278 (12) | 0.0310 (12) | 0.0277 (12) | 0.0008 (10) | 0.0047 (10) | −0.0025 (10) |
C10 | 0.0317 (14) | 0.0430 (15) | 0.0408 (15) | 0.0027 (11) | 0.0086 (11) | 0.0073 (12) |
C11 | 0.053 (2) | 0.0488 (17) | 0.0434 (18) | 0.0089 (14) | 0.0141 (15) | 0.0111 (14) |
C12 | 0.0468 (19) | 0.0555 (17) | 0.0416 (17) | 0.0169 (15) | −0.0043 (14) | 0.0077 (15) |
C13 | 0.0282 (14) | 0.0584 (19) | 0.0552 (19) | 0.0045 (13) | −0.0045 (13) | −0.0003 (15) |
C14 | 0.0278 (13) | 0.0440 (15) | 0.0476 (17) | −0.0006 (11) | 0.0057 (12) | 0.0014 (13) |
C15 | 0.0272 (13) | 0.0322 (12) | 0.0307 (14) | −0.0001 (10) | 0.0074 (11) | 0.0013 (10) |
C16 | 0.071 (2) | 0.0544 (18) | 0.0366 (16) | −0.0258 (16) | 0.0225 (15) | −0.0101 (14) |
C17 | 0.073 (2) | 0.0522 (19) | 0.058 (2) | −0.0321 (17) | 0.0262 (18) | −0.0163 (16) |
C18 | 0.0460 (17) | 0.0375 (15) | 0.065 (2) | −0.0062 (13) | 0.0236 (15) | 0.0048 (14) |
C19 | 0.063 (2) | 0.0566 (19) | 0.0454 (18) | −0.0115 (16) | 0.0258 (16) | 0.0068 (15) |
C20 | 0.0475 (17) | 0.0475 (16) | 0.0347 (15) | −0.0081 (14) | 0.0130 (13) | −0.0026 (13) |
C21 | 0.0286 (12) | 0.0320 (12) | 0.0313 (13) | −0.0033 (10) | 0.0075 (10) | −0.0024 (10) |
C22 | 0.0412 (16) | 0.0441 (16) | 0.0461 (17) | 0.0063 (13) | 0.0058 (13) | −0.0101 (13) |
C23 | 0.070 (2) | 0.0463 (18) | 0.051 (2) | 0.0108 (16) | 0.0193 (17) | −0.0132 (15) |
C24 | 0.077 (2) | 0.0396 (16) | 0.0308 (15) | −0.0081 (15) | 0.0081 (15) | −0.0078 (12) |
C25 | 0.0507 (17) | 0.0447 (16) | 0.0293 (15) | −0.0093 (13) | −0.0016 (13) | 0.0037 (12) |
C26 | 0.0350 (14) | 0.0375 (14) | 0.0326 (13) | −0.0003 (11) | 0.0045 (11) | 0.0016 (12) |
Hg1—C8 | 2.244 (3) | C11—C12 | 1.375 (5) |
Hg1—Cl2 | 2.3916 (9) | C11—H11A | 0.9300 |
Hg1—Cl1i | 2.5840 (8) | C12—C13 | 1.381 (5) |
Hg1—Cl1 | 2.7876 (8) | C12—H12A | 0.9300 |
P1—C8 | 1.789 (3) | C13—C14 | 1.384 (4) |
P1—C21 | 1.800 (3) | C13—H13A | 0.9300 |
P1—C9 | 1.800 (2) | C14—H14A | 0.9300 |
P1—C15 | 1.812 (3) | C15—C20 | 1.380 (4) |
C1—C6 | 1.386 (5) | C15—C16 | 1.384 (4) |
C1—C2 | 1.393 (4) | C16—C17 | 1.383 (4) |
C1—C7 | 1.511 (3) | C16—H16A | 0.9300 |
C2—C3 | 1.366 (4) | C17—C18 | 1.362 (4) |
C2—H2A | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.377 (5) | C18—C19 | 1.370 (4) |
C3—N1 | 1.480 (4) | C18—H18A | 0.9300 |
C4—C5 | 1.374 (5) | C19—C20 | 1.379 (4) |
C4—H4A | 0.9300 | C19—H19A | 0.9300 |
C5—C6 | 1.392 (4) | C20—H20A | 0.9300 |
C5—H5A | 0.9300 | C21—C26 | 1.391 (4) |
C6—H6A | 0.9300 | C21—C22 | 1.392 (4) |
C7—O3 | 1.222 (3) | C22—C23 | 1.380 (4) |
C7—C8 | 1.470 (3) | C22—H22A | 0.9300 |
N1—O1 | 1.211 (4) | C23—C24 | 1.370 (5) |
N1—O2 | 1.214 (4) | C23—H23A | 0.9300 |
C8—H8A | 0.9800 | C24—C25 | 1.371 (4) |
C9—C10 | 1.394 (4) | C24—H24A | 0.9300 |
C9—C14 | 1.398 (3) | C25—C26 | 1.384 (4) |
C10—C11 | 1.380 (4) | C25—H25A | 0.9300 |
C10—H10A | 0.9300 | C26—H26A | 0.9300 |
C8—Hg1—Cl2 | 134.44 (7) | C12—C11—C10 | 120.3 (3) |
C8—Hg1—Cl1i | 106.18 (7) | C12—C11—H11A | 119.8 |
Cl2—Hg1—Cl1i | 109.38 (3) | C10—C11—H11A | 119.8 |
C8—Hg1—Cl1 | 94.37 (7) | C11—C12—C13 | 120.0 (3) |
Cl2—Hg1—Cl1 | 101.66 (3) | C11—C12—H12A | 120.0 |
Cl1i—Hg1—Cl1 | 106.661 (16) | C13—C12—H12A | 120.0 |
Hg1ii—Cl1—Hg1 | 140.15 (3) | C12—C13—C14 | 120.6 (3) |
C8—P1—C21 | 112.58 (12) | C12—C13—H13A | 119.7 |
C8—P1—C9 | 113.21 (12) | C14—C13—H13A | 119.7 |
C21—P1—C9 | 110.32 (12) | C13—C14—C9 | 119.5 (3) |
C8—P1—C15 | 107.04 (12) | C13—C14—H14A | 120.2 |
C21—P1—C15 | 105.74 (12) | C9—C14—H14A | 120.2 |
C9—P1—C15 | 107.48 (12) | C20—C15—C16 | 118.8 (3) |
C6—C1—C2 | 119.3 (2) | C20—C15—P1 | 120.8 (2) |
C6—C1—C7 | 124.2 (2) | C16—C15—P1 | 120.4 (2) |
C2—C1—C7 | 116.5 (2) | C17—C16—C15 | 120.1 (3) |
C3—C2—C1 | 119.1 (3) | C17—C16—H16A | 120.0 |
C3—C2—H2A | 120.5 | C15—C16—H16A | 120.0 |
C1—C2—H2A | 120.5 | C18—C17—C16 | 120.9 (3) |
C2—C3—C4 | 122.4 (3) | C18—C17—H17A | 119.5 |
C2—C3—N1 | 118.2 (3) | C16—C17—H17A | 119.5 |
C4—C3—N1 | 119.4 (3) | C17—C18—C19 | 119.1 (3) |
C5—C4—C3 | 118.8 (3) | C17—C18—H18A | 120.4 |
C5—C4—H4A | 120.6 | C19—C18—H18A | 120.4 |
C3—C4—H4A | 120.6 | C18—C19—C20 | 120.9 (3) |
C4—C5—C6 | 120.1 (3) | C18—C19—H19A | 119.5 |
C4—C5—H5A | 119.9 | C20—C19—H19A | 119.5 |
C6—C5—H5A | 119.9 | C19—C20—C15 | 120.2 (3) |
C1—C6—C5 | 120.3 (3) | C19—C20—H20A | 119.9 |
C1—C6—H6A | 119.9 | C15—C20—H20A | 119.9 |
C5—C6—H6A | 119.9 | C26—C21—C22 | 119.0 (2) |
O3—C7—C8 | 121.3 (2) | C26—C21—P1 | 121.8 (2) |
O3—C7—C1 | 118.9 (2) | C22—C21—P1 | 118.75 (19) |
C8—C7—C1 | 119.7 (2) | C23—C22—C21 | 119.9 (3) |
O1—N1—O2 | 124.3 (4) | C23—C22—H22A | 120.1 |
O1—N1—C3 | 118.5 (3) | C21—C22—H22A | 120.1 |
O2—N1—C3 | 117.2 (4) | C24—C23—C22 | 121.0 (3) |
C7—C8—P1 | 113.71 (18) | C24—C23—H23A | 119.5 |
C7—C8—Hg1 | 105.71 (17) | C22—C23—H23A | 119.5 |
P1—C8—Hg1 | 108.21 (12) | C23—C24—C25 | 119.6 (3) |
C7—C8—H8A | 109.7 | C23—C24—H24A | 120.2 |
P1—C8—H8A | 109.7 | C25—C24—H24A | 120.2 |
Hg1—C8—H8A | 109.7 | C24—C25—C26 | 120.7 (3) |
C10—C9—C14 | 119.3 (2) | C24—C25—H25A | 119.6 |
C10—C9—P1 | 121.04 (19) | C26—C25—H25A | 119.6 |
C14—C9—P1 | 119.6 (2) | C25—C26—C21 | 119.8 (3) |
C11—C10—C9 | 120.2 (3) | C25—C26—H26A | 120.1 |
C11—C10—H10A | 119.9 | C21—C26—H26A | 120.1 |
C9—C10—H10A | 119.9 | ||
C8—Hg1—Cl1—Hg1ii | −130.02 (8) | C8—P1—C9—C14 | 137.1 (2) |
Cl2—Hg1—Cl1—Hg1ii | 92.86 (5) | C21—P1—C9—C14 | −95.7 (2) |
Cl1i—Hg1—Cl1—Hg1ii | −21.69 (4) | C15—P1—C9—C14 | 19.1 (2) |
C6—C1—C2—C3 | 0.0 (4) | C14—C9—C10—C11 | −2.4 (4) |
C7—C1—C2—C3 | 179.5 (2) | P1—C9—C10—C11 | 175.7 (2) |
C1—C2—C3—C4 | 0.6 (4) | C9—C10—C11—C12 | 0.8 (5) |
C1—C2—C3—N1 | −179.4 (3) | C10—C11—C12—C13 | 1.4 (5) |
C2—C3—C4—C5 | −0.6 (6) | C11—C12—C13—C14 | −2.1 (5) |
N1—C3—C4—C5 | 179.4 (3) | C12—C13—C14—C9 | 0.5 (5) |
C3—C4—C5—C6 | −0.1 (6) | C10—C9—C14—C13 | 1.7 (4) |
C2—C1—C6—C5 | −0.6 (4) | P1—C9—C14—C13 | −176.4 (2) |
C7—C1—C6—C5 | 180.0 (3) | C8—P1—C15—C20 | 118.7 (2) |
C4—C5—C6—C1 | 0.6 (5) | C21—P1—C15—C20 | −1.6 (3) |
C6—C1—C7—O3 | −174.2 (2) | C9—P1—C15—C20 | −119.4 (2) |
C2—C1—C7—O3 | 6.3 (4) | C8—P1—C15—C16 | −62.0 (3) |
C6—C1—C7—C8 | 9.0 (4) | C21—P1—C15—C16 | 177.8 (2) |
C2—C1—C7—C8 | −170.5 (2) | C9—P1—C15—C16 | 59.9 (3) |
C2—C3—N1—O1 | 13.9 (5) | C20—C15—C16—C17 | −0.5 (5) |
C4—C3—N1—O1 | −166.0 (4) | P1—C15—C16—C17 | −179.8 (3) |
C2—C3—N1—O2 | −167.6 (3) | C15—C16—C17—C18 | 0.6 (5) |
C4—C3—N1—O2 | 12.4 (5) | C16—C17—C18—C19 | −0.3 (5) |
O3—C7—C8—P1 | −26.8 (3) | C17—C18—C19—C20 | −0.1 (5) |
C1—C7—C8—P1 | 149.97 (19) | C18—C19—C20—C15 | 0.2 (5) |
O3—C7—C8—Hg1 | 91.8 (2) | C16—C15—C20—C19 | 0.1 (4) |
C1—C7—C8—Hg1 | −91.5 (2) | P1—C15—C20—C19 | 179.4 (2) |
C21—P1—C8—C7 | −42.2 (2) | C8—P1—C21—C26 | −21.5 (3) |
C9—P1—C8—C7 | 83.8 (2) | C9—P1—C21—C26 | −149.0 (2) |
C15—P1—C8—C7 | −157.94 (19) | C15—P1—C21—C26 | 95.0 (2) |
C21—P1—C8—Hg1 | −159.28 (11) | C8—P1—C21—C22 | 166.2 (2) |
C9—P1—C8—Hg1 | −33.30 (16) | C9—P1—C21—C22 | 38.7 (2) |
C15—P1—C8—Hg1 | 84.95 (14) | C15—P1—C21—C22 | −77.2 (2) |
Cl2—Hg1—C8—C7 | −143.68 (13) | C26—C21—C22—C23 | −0.8 (4) |
Cl1i—Hg1—C8—C7 | −3.47 (17) | P1—C21—C22—C23 | 171.7 (2) |
Cl1—Hg1—C8—C7 | 105.29 (15) | C21—C22—C23—C24 | 1.6 (5) |
Cl2—Hg1—C8—P1 | −21.53 (18) | C22—C23—C24—C25 | −0.7 (5) |
Cl1i—Hg1—C8—P1 | 118.69 (11) | C23—C24—C25—C26 | −1.0 (5) |
Cl1—Hg1—C8—P1 | −132.55 (11) | C24—C25—C26—C21 | 1.7 (4) |
C8—P1—C9—C10 | −40.9 (3) | C22—C21—C26—C25 | −0.8 (4) |
C21—P1—C9—C10 | 86.2 (2) | P1—C21—C26—C25 | −173.1 (2) |
C15—P1—C9—C10 | −158.9 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O3 | 0.93 | 2.33 | 3.118 (3) | 142 |
C6—H6A···Cl1 | 0.93 | 2.83 | 3.630 (3) | 145 |
C24—H24A···O3iii | 0.93 | 2.39 | 3.206 (3) | 146 |
Symmetry code: (iii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [HgCl2(C26H20NO3P)] |
Mr | 696.89 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.589 (3), 8.1026 (17), 25.231 (6) |
β (°) | 105.174 (2) |
V (Å3) | 2483.8 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 6.51 |
Crystal size (mm) | 0.61 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.109, 0.499 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29804, 6143, 5049 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.067, 1.03 |
No. of reflections | 6143 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.96, −0.45 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O3 | 0.93 | 2.33 | 3.118 (3) | 142.2 |
C6—H6A···Cl1 | 0.93 | 2.83 | 3.630 (3) | 145.1 |
C24—H24A···O3i | 0.93 | 2.39 | 3.206 (3) | 145.7 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Acknowledgements
The authors are grateful to Urmia University for financial support and to Dr Amitava Choudhruy (Missouri University of Science and Technology, USA) for his assistance with the X-ray crystallography.
References
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The coordination chemistry of ambidentate ligands (L) has been investigated. The preparation and characterization of stabilized phosphorus ylides, and metal complexes incorporating this type of ylides, has attracted much attention in recent years (Ebrahim et al., 2007). Although many bonding modes are possible for keto-ylides, coordination through ylides methine carbon is more predominant and observed with soft metal ions, e.g. Pd(II), Pt(II), HgII and Au(I), whereas O-coordination dominates when the metals involved are hard, e.g. Ti(IV), Zr(IV), and Hf(IV). The crystal and molecular structure of the title complex reveals a polymeric structure, with HgII ions linked by bridging chlorine, participating in a very asymmetric linear bridge. The asymmetric ligand plays an important role in the building of this unusual supramolecular structure. The building unit (Fig. 1) is repeated in the polymeric crystal structure. The polymeric structure (part of the chain) and packing diagram for the complex are shown in Fig. 2 and Fig. 3, respectively. The X-ray analysis reveals the coordination of the ylide ligand through the methine C atom only. The HgII atom is located in a distorted tetrahedral environment, with one terminal Cl- and two bridging Cl- ions, and one C atom from the ligand, resulting in a one-dimensional polymeric chain. The bond angles around HgII ion indicate a severe distortion from ideal tetrahedral geometry. The Hg—Cl(terminal) bond length, 2.3916 (9) Å, is shorter than Hg—Cl(bridging) distances. The asymmetric bridging nature of the two chloro ligands is reflected in the unequal Hg—Cl distances of 2.5840 (8) and 2.7876 (8) Å. The latter distance being rather long, indicates a weak Hg—Cl(bridging) interaction. The Hg—C bond length in the title compound, 2.244 (3) Å, is consistent with values reported for mono ([HgI2(bbtppy)(DMSO)]) and dimeric ([(bappy)HgI2]2) HgII—C complexes (Sabounchei et al., 2007, 2008, 2009, 2011; Sabounchei, Jodaian et al., 2010; Sabounchei, Samiee et al., 2010). In the crystal structure, adjacent polymer chains interact via C—H···O hydrogen bonds. Intramolecular C—H···O and weak C—H···Cl hydrogen bonds stabilize the polymeric chains.