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In the centrosymmetric molecule of the title compound, [Hg(C12H10O2P)2(C5H5N)2(C12H11O2P)2], the approximately octa­hedral Hg atom is coordinated by two each of phenyl­phosphinate, phosphinic acid and pyridine ligands. Each pair of phosphinic acid and phosphinate ligands features an intra­molecular hydrogen bond, so forming an eight-membered ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009469/om6291sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009469/om6291Isup2.hkl
Contains datablock I

CCDC reference: 264149

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.047
  • wR factor = 0.115
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

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Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.09 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Collect (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Crystal Impact, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(diphenylphosphinato-κO)bis(diphenylphosphinic acid-κO)bis(pyridine-κN)mercury(II) top
Crystal data top
[Hg(C12H10O2P)2(C5H5N)2(C12H11O2P)2]Z = 1
Mr = 1229.49F(000) = 618
Triclinic, P1Dx = 1.523 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4511 (3) ÅCell parameters from 27102 reflections
b = 12.3528 (5) Åθ = 2.9–27.5°
c = 12.6391 (4) ŵ = 3.05 mm1
α = 101.853 (2)°T = 200 K
β = 109.278 (2)°Prism, colorless
γ = 95.797 (2)°0.30 × 0.12 × 0.08 mm
V = 1340.19 (8) Å3
Data collection top
Nonius KappaCCD
diffractometer
6145 independent reflections
Radiation source: Enraf–Nonius FR5905482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
CCD rotation images, thick slices scansθmax = 27.7°, θmin = 3.1°
Absorption correction: multi-scan
SADABS (Bruker, 2004)
h = 1211
Tmin = 0.630, Tmax = 0.784k = 1615
25466 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0663P)2 + 1.7278P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
6145 reflectionsΔρmax = 3.14 e Å3
332 parametersΔρmin = 1.51 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (10)
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
xyzUiso*/Ueq
Hg000.50.02908 (12)
P10.04995 (14)0.22697 (10)0.72322 (11)0.0289 (3)
P20.05597 (14)0.10971 (10)0.25214 (10)0.0273 (3)
O110.1006 (4)0.1574 (3)0.6019 (3)0.0402 (9)
O120.0763 (4)0.1714 (3)0.8148 (3)0.0345 (8)
O210.0820 (4)0.1152 (3)0.3764 (3)0.0331 (8)
O220.0290 (4)0.0009 (3)0.1629 (3)0.0316 (7)
H220.01720.05320.17980.047*
N10.2394 (4)0.0420 (3)0.6090 (3)0.0269 (8)
C10.3420 (6)0.0624 (4)0.5598 (4)0.0321 (10)
H10.30760.0560.47880.039*
C20.4965 (6)0.0926 (4)0.6242 (4)0.0335 (11)
H20.5670.1070.58760.04*
C30.5474 (6)0.1016 (5)0.7415 (5)0.0360 (11)
H30.6530.12280.78720.043*
C40.4412 (6)0.0792 (5)0.7916 (4)0.0349 (11)
H40.47310.08380.87230.042*
C50.2888 (5)0.0502 (4)0.7232 (4)0.0292 (10)
H50.21630.03550.7580.035*
C1110.1518 (5)0.2851 (4)0.7752 (4)0.0291 (10)
C1120.2174 (6)0.3126 (5)0.6981 (5)0.0400 (12)
H1120.15770.29880.61810.048*
C1130.3722 (7)0.3607 (5)0.7397 (6)0.0481 (15)
H1130.41790.38080.68820.058*
C1140.4579 (6)0.3789 (5)0.8553 (6)0.0483 (15)
H1140.5630.41140.88310.058*
C1150.3939 (6)0.3506 (5)0.9318 (6)0.0444 (14)
H1150.45440.36381.01160.053*
C1160.2400 (6)0.3025 (4)0.8914 (5)0.0341 (11)
H1160.19560.28160.94330.041*
C1210.1424 (6)0.3468 (4)0.7285 (5)0.0356 (11)
C1220.2221 (8)0.3733 (6)0.6265 (7)0.0619 (18)
H1220.23060.32720.55380.074*
C1230.2895 (10)0.4682 (8)0.6319 (10)0.085 (3)
H1230.34880.4840.56180.103*
C1240.2731 (9)0.5389 (6)0.7346 (11)0.078 (3)
H1240.31650.6050.73630.093*
C1250.1938 (8)0.5137 (5)0.8344 (8)0.064 (2)
H1250.18320.56210.90660.077*
C1260.1282 (7)0.4187 (5)0.8330 (6)0.0452 (14)
H1260.07290.40240.90390.054*
C2110.0512 (5)0.2157 (4)0.2075 (4)0.0292 (10)
C2120.0541 (6)0.3063 (5)0.2925 (5)0.0396 (12)
H2120.0050.30950.37220.048*
C2130.1295 (7)0.3920 (5)0.2600 (6)0.0465 (14)
H2130.13030.45440.31780.056*
C2140.2026 (6)0.3872 (5)0.1451 (6)0.0450 (14)
H2140.2540.4460.12360.054*
C2150.2014 (6)0.2967 (5)0.0609 (5)0.0422 (13)
H2150.2530.29320.01850.051*
C2160.1262 (6)0.2114 (5)0.0909 (5)0.0358 (11)
H2160.12540.14970.03220.043*
C2210.2352 (5)0.1409 (4)0.2327 (4)0.0304 (10)
C2220.2407 (6)0.1150 (5)0.1221 (5)0.0383 (12)
H2220.15040.07930.05770.046*
C2230.3757 (7)0.1403 (6)0.1045 (6)0.0495 (15)
H2230.3770.1230.02810.059*
C2240.5086 (7)0.1904 (6)0.1971 (6)0.0530 (16)
H2240.60150.20660.18480.064*
C2250.5052 (7)0.2164 (5)0.3065 (6)0.0508 (15)
H2250.59670.25090.37030.061*
C2260.3694 (6)0.1931 (5)0.3264 (5)0.0379 (12)
H2260.36840.21250.40290.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg0.02206 (15)0.03481 (18)0.02776 (16)0.00499 (10)0.00724 (10)0.00536 (10)
P10.0247 (6)0.0257 (6)0.0337 (6)0.0048 (5)0.0093 (5)0.0039 (5)
P20.0264 (6)0.0273 (6)0.0290 (6)0.0044 (5)0.0089 (5)0.0112 (5)
O110.040 (2)0.033 (2)0.037 (2)0.0085 (15)0.0058 (16)0.0013 (15)
O120.0301 (18)0.0312 (18)0.044 (2)0.0046 (14)0.0170 (16)0.0083 (15)
O210.0334 (19)0.038 (2)0.0301 (17)0.0067 (15)0.0109 (14)0.0131 (15)
O220.0275 (17)0.0292 (18)0.0362 (18)0.0052 (13)0.0073 (14)0.0107 (14)
N10.0219 (19)0.031 (2)0.029 (2)0.0082 (15)0.0096 (16)0.0081 (16)
C10.027 (2)0.038 (3)0.034 (2)0.008 (2)0.014 (2)0.007 (2)
C20.027 (2)0.041 (3)0.037 (3)0.009 (2)0.018 (2)0.007 (2)
C30.023 (2)0.041 (3)0.040 (3)0.011 (2)0.007 (2)0.005 (2)
C40.029 (3)0.044 (3)0.029 (2)0.008 (2)0.006 (2)0.008 (2)
C50.026 (2)0.033 (3)0.030 (2)0.0060 (19)0.0124 (19)0.0072 (19)
C1110.028 (2)0.019 (2)0.038 (3)0.0062 (17)0.012 (2)0.0021 (19)
C1120.041 (3)0.032 (3)0.053 (3)0.008 (2)0.022 (3)0.014 (2)
C1130.045 (3)0.039 (3)0.075 (4)0.013 (3)0.034 (3)0.023 (3)
C1140.028 (3)0.036 (3)0.080 (5)0.007 (2)0.017 (3)0.015 (3)
C1150.033 (3)0.034 (3)0.054 (3)0.007 (2)0.002 (2)0.006 (2)
C1160.031 (3)0.025 (2)0.043 (3)0.0066 (19)0.010 (2)0.005 (2)
C1210.028 (3)0.027 (3)0.047 (3)0.0013 (19)0.010 (2)0.008 (2)
C1220.053 (4)0.054 (4)0.070 (4)0.020 (3)0.006 (3)0.019 (3)
C1230.058 (5)0.077 (6)0.123 (8)0.026 (4)0.012 (5)0.058 (6)
C1240.049 (4)0.031 (4)0.173 (10)0.019 (3)0.055 (5)0.039 (5)
C1250.055 (4)0.032 (3)0.119 (7)0.012 (3)0.052 (4)0.010 (4)
C1260.042 (3)0.033 (3)0.066 (4)0.008 (2)0.030 (3)0.006 (3)
C2110.024 (2)0.031 (3)0.034 (2)0.0041 (18)0.0114 (19)0.011 (2)
C2120.034 (3)0.042 (3)0.040 (3)0.009 (2)0.010 (2)0.009 (2)
C2130.042 (3)0.035 (3)0.056 (4)0.011 (2)0.013 (3)0.003 (3)
C2140.035 (3)0.035 (3)0.066 (4)0.012 (2)0.012 (3)0.023 (3)
C2150.036 (3)0.044 (3)0.047 (3)0.010 (2)0.007 (2)0.022 (3)
C2160.036 (3)0.035 (3)0.036 (3)0.009 (2)0.009 (2)0.011 (2)
C2210.029 (2)0.028 (2)0.036 (3)0.0038 (19)0.010 (2)0.013 (2)
C2220.037 (3)0.044 (3)0.036 (3)0.010 (2)0.013 (2)0.016 (2)
C2230.054 (4)0.058 (4)0.054 (4)0.018 (3)0.032 (3)0.027 (3)
C2240.041 (3)0.058 (4)0.076 (5)0.010 (3)0.031 (3)0.034 (3)
C2250.031 (3)0.050 (4)0.061 (4)0.004 (2)0.006 (3)0.013 (3)
C2260.034 (3)0.040 (3)0.034 (3)0.000 (2)0.008 (2)0.009 (2)
Geometric parameters (Å, º) top
Hg—N12.168 (4)C121—C1221.385 (9)
Hg—O112.549 (4)C121—C1261.388 (8)
Hg—O212.561 (3)C122—C1231.389 (11)
P1—O111.487 (4)C122—H1220.95
P1—O121.534 (4)C123—C1241.359 (14)
P1—C1211.794 (5)C123—H1230.95
P1—C1111.812 (5)C124—C1251.355 (13)
P2—O211.493 (4)C124—H1240.95
P2—O221.527 (4)C125—C1261.381 (9)
P2—C2111.804 (5)C125—H1250.95
P2—C2211.806 (5)C126—H1260.95
O22—H220.84C211—C2121.392 (7)
N1—C51.340 (6)C211—C2161.396 (7)
N1—C11.343 (6)C212—C2131.391 (8)
C1—C21.384 (7)C212—H2120.95
C1—H10.95C213—C2141.372 (9)
C2—C31.376 (7)C213—H2130.95
C2—H20.95C214—C2151.380 (9)
C3—C41.386 (7)C214—H2140.95
C3—H30.95C215—C2161.377 (8)
C4—C51.377 (7)C215—H2150.95
C4—H40.95C216—H2160.95
C5—H50.95C221—C2221.388 (7)
C111—C1161.387 (7)C221—C2261.399 (7)
C111—C1121.395 (8)C222—C2231.382 (8)
C112—C1131.399 (8)C222—H2220.95
C112—H1120.95C223—C2241.381 (10)
C113—C1141.374 (10)C223—H2230.95
C113—H1130.95C224—C2251.365 (10)
C114—C1151.380 (9)C224—H2240.95
C114—H1140.95C225—C2261.401 (8)
C115—C1161.392 (8)C225—H2250.95
C115—H1150.95C226—H2260.95
C116—H1160.95
N1—Hg—O11i79.77 (13)C111—C116—C115119.9 (5)
N1—Hg—O11100.23 (13)C111—C116—H116120.0
N1—Hg—O21i95.71 (13)C115—C116—H116120.0
O11i—Hg—O21i95.02 (12)C122—C121—C126118.5 (6)
O11—Hg—O21i84.98 (12)C122—C121—P1119.7 (5)
N1—Hg—O2184.29 (13)C126—C121—P1121.6 (4)
N1i—Hg—O2195.71 (13)C121—C122—C123119.2 (8)
O11i—Hg—O2184.98 (12)C121—C122—H122120.4
O11—Hg—O2195.02 (12)C123—C122—H122120.4
O11—P1—O12118.1 (2)C124—C123—C122121.8 (8)
O11—P1—C121110.0 (2)C124—C123—H123119.1
O12—P1—C121105.8 (2)C122—C123—H123119.1
O11—P1—C111110.1 (2)C125—C124—C123119.0 (7)
O12—P1—C111106.9 (2)C125—C124—H124120.5
C121—P1—C111105.0 (2)C123—C124—H124120.5
O21—P2—O22117.7 (2)C124—C125—C126121.0 (8)
O21—P2—C211109.9 (2)C124—C125—H125119.5
O22—P2—C211105.9 (2)C126—C125—H125119.5
O21—P2—C221110.5 (2)C125—C126—C121120.4 (7)
O22—P2—C221106.0 (2)C125—C126—H126119.8
C211—P2—C221106.3 (2)C121—C126—H126119.8
P1—O11—Hg133.7 (2)C212—C211—C216119.5 (5)
P2—O21—Hg139.8 (2)C212—C211—P2118.5 (4)
P2—O22—H22109.5C216—C211—P2121.9 (4)
C5—N1—C1118.9 (4)C213—C212—C211119.6 (5)
C5—N1—Hg122.9 (3)C213—C212—H212120.2
C1—N1—Hg118.2 (3)C211—C212—H212120.2
N1—C1—C2121.7 (5)C214—C213—C212120.6 (6)
N1—C1—H1119.2C214—C213—H213119.7
C2—C1—H1119.2C212—C213—H213119.7
C3—C2—C1119.5 (5)C213—C214—C215119.8 (5)
C3—C2—H2120.2C213—C214—H214120.1
C1—C2—H2120.2C215—C214—H214120.1
C2—C3—C4118.6 (5)C216—C215—C214120.7 (5)
C2—C3—H3120.7C216—C215—H215119.6
C4—C3—H3120.7C214—C215—H215119.6
C5—C4—C3119.2 (5)C215—C216—C211119.8 (5)
C5—C4—H4120.4C215—C216—H216120.1
C3—C4—H4120.4C211—C216—H216120.1
N1—C5—C4122.1 (4)C222—C221—C226118.7 (5)
N1—C5—H5118.9C222—C221—P2119.7 (4)
C4—C5—H5118.9C226—C221—P2121.7 (4)
C116—C111—C112120.3 (5)C223—C222—C221120.8 (5)
C116—C111—P1120.0 (4)C223—C222—H222119.6
C112—C111—P1119.7 (4)C221—C222—H222119.6
C111—C112—C113119.3 (6)C224—C223—C222120.5 (6)
C111—C112—H112120.4C224—C223—H223119.7
C113—C112—H112120.4C222—C223—H223119.7
C114—C113—C112119.9 (6)C225—C224—C223119.4 (6)
C114—C113—H113120.1C225—C224—H224120.3
C112—C113—H113120.1C223—C224—H224120.3
C113—C114—C115121.1 (5)C224—C225—C226121.2 (6)
C113—C114—H114119.4C224—C225—H225119.4
C115—C114—H114119.4C226—C225—H225119.4
C114—C115—C116119.6 (6)C221—C226—C225119.4 (5)
C114—C115—H115120.2C221—C226—H226120.3
C116—C115—H115120.2C225—C226—H226120.3
O12—P1—O11—Hg73.5 (4)C114—C115—C116—C1111.1 (8)
C121—P1—O11—Hg165.0 (3)O11—P1—C121—C12211.5 (6)
C111—P1—O11—Hg49.7 (4)O12—P1—C121—C122140.2 (5)
N1—Hg—O11—P126.9 (3)C111—P1—C121—C122107.0 (5)
N1i—Hg—O11—P1153.1 (3)O11—P1—C121—C126172.7 (4)
O21i—Hg—O11—P168.0 (3)O12—P1—C121—C12644.1 (5)
O21—Hg—O11—P1112.0 (3)C111—P1—C121—C12668.8 (5)
O22—P2—O21—Hg10.1 (4)C126—C121—C122—C1232.3 (10)
C211—P2—O21—Hg111.1 (3)P1—C121—C122—C123178.1 (6)
C221—P2—O21—Hg131.9 (3)C121—C122—C123—C1243.4 (13)
N1—Hg—O21—P2136.2 (3)C122—C123—C124—C1252.7 (13)
N1i—Hg—O21—P243.8 (3)C123—C124—C125—C1261.0 (11)
O11i—Hg—O21—P256.1 (3)C124—C125—C126—C1210.0 (10)
O11—Hg—O21—P2123.9 (3)C122—C121—C126—C1250.7 (9)
O11i—Hg—N1—C5122.3 (4)P1—C121—C126—C125176.5 (5)
O11—Hg—N1—C557.7 (4)O21—P2—C211—C21219.6 (5)
O21i—Hg—N1—C528.3 (4)O22—P2—C211—C212147.7 (4)
O21—Hg—N1—C5151.7 (4)C221—P2—C211—C21299.9 (4)
O11i—Hg—N1—C158.8 (4)O21—P2—C211—C216162.6 (4)
O11—Hg—N1—C1121.2 (4)O22—P2—C211—C21634.6 (5)
O21i—Hg—N1—C1152.9 (4)C221—P2—C211—C21677.9 (5)
O21—Hg—N1—C127.1 (4)C216—C211—C212—C2131.1 (8)
C5—N1—C1—C20.6 (7)P2—C211—C212—C213176.7 (4)
Hg—N1—C1—C2178.3 (4)C211—C212—C213—C2140.9 (9)
N1—C1—C2—C30.3 (8)C212—C213—C214—C2150.1 (9)
C1—C2—C3—C40.5 (8)C213—C214—C215—C2160.6 (9)
C2—C3—C4—C50.8 (8)C214—C215—C216—C2110.5 (8)
C1—N1—C5—C40.2 (7)C212—C211—C216—C2150.4 (8)
Hg—N1—C5—C4178.6 (4)P2—C211—C216—C215177.4 (4)
C3—C4—C5—N10.5 (8)O21—P2—C221—C222164.8 (4)
O11—P1—C111—C116147.7 (4)O22—P2—C221—C22236.4 (5)
O12—P1—C111—C11618.2 (4)C211—P2—C221—C22276.0 (5)
C121—P1—C111—C11693.9 (4)O21—P2—C221—C22616.5 (5)
O11—P1—C111—C11232.6 (5)O22—P2—C221—C226145.0 (4)
O12—P1—C111—C112162.1 (4)C211—P2—C221—C226102.6 (5)
C121—P1—C111—C11285.8 (4)C226—C221—C222—C2230.2 (8)
C116—C111—C112—C1131.7 (8)P2—C221—C222—C223178.5 (4)
P1—C111—C112—C113178.0 (4)C221—C222—C223—C2241.1 (9)
C111—C112—C113—C1140.9 (8)C222—C223—C224—C2251.0 (10)
C112—C113—C114—C1150.1 (9)C223—C224—C225—C2260.0 (10)
C113—C114—C115—C1160.2 (9)C222—C221—C226—C2250.8 (8)
C112—C111—C116—C1151.8 (7)P2—C221—C226—C225179.4 (4)
P1—C111—C116—C115177.9 (4)C224—C225—C226—C2210.8 (9)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22—H22···O12i0.841.622.447 (5)167
Symmetry code: (i) x, y, z+1.
 

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