The title compound, {(C18H34N2O8)[Hg4I10]}n, contains two subunits, namely doubly protonated N,N,N′,N′-tetrakis[3-(methoxycarbonyl)propyl]ethylenediammonium cations and macroanionic pentaiododimercurate [Hg2I5−]n chains. The complete cation is generated by twofold symmetry and the polymeric anion contains corner- and edge-shared HgI3 and HgI4 polyhedra.
Supporting information
CCDC reference: 624541
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.018 Å
- Disorder in main residue
- R factor = 0.054
- wR factor = 0.115
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.90 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.85 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Hg1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Hg2A
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Hg1A
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for Hg2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for I1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for I2
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for I4
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26
PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 18
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
16 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL/NT (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/NT; software used to prepare material for publication: SHELXL97.
Poly[
N,
N,
N',
N'-Tetrakis[3-(methoxycarbonyl)propyl]ethylenediammonium [tetra-µ-iodo-hexaiodotetramercurate]]
top
Crystal data top
(C18H34N2O8)[Hg4I10] | F(000) = 4280 |
Mr = 2477.84 | Dx = 3.608 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 250 reflections |
a = 18.580 (5) Å | θ = 2.0–25.5° |
b = 16.805 (4) Å | µ = 20.23 mm−1 |
c = 14.864 (4) Å | T = 298 K |
β = 100.632 (5)° | Block, yellow |
V = 4561 (2) Å3 | 0.11 × 0.10 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4237 independent reflections |
Radiation source: fine-focus sealed tube | 2702 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 25.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −22→20 |
Tmin = 0.122, Tmax = 0.290 | k = −20→17 |
11521 measured reflections | l = −18→10 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0369P)2] where P = (Fo2 + 2Fc2)/3 |
4237 reflections | (Δ/σ)max = 0.001 |
209 parameters | Δρmax = 1.66 e Å−3 |
6 restraints | Δρmin = −1.32 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 | Occ. (<1) |
C1 | 0.0418 (6) | 0.3147 (6) | 0.2542 (8) | 0.030 (3) | |
H1A | 0.0584 | 0.3684 | 0.2450 | 0.036* | |
H1B | 0.0643 | 0.2980 | 0.3154 | 0.036* | |
C2 | 0.0500 (8) | 0.2954 (7) | 0.0891 (8) | 0.041 (3) | |
H2A | 0.0883 | 0.3331 | 0.0829 | 0.050* | |
H2B | 0.0041 | 0.3242 | 0.0813 | 0.050* | |
C3 | 0.0453 (8) | 0.2320 (8) | 0.0141 (9) | 0.051 (4) | |
H3A | 0.0372 | 0.2576 | −0.0454 | 0.061* | |
H3B | 0.0913 | 0.2032 | 0.0215 | 0.061* | |
C4 | −0.0151 (9) | 0.1755 (8) | 0.0185 (9) | 0.043 (4) | |
C5 | 0.1482 (7) | 0.2389 (7) | 0.2110 (9) | 0.038 (3) | |
H5A | 0.1651 | 0.2180 | 0.1577 | 0.045* | |
H5B | 0.1754 | 0.2874 | 0.2294 | 0.045* | |
C6 | 0.1641 (8) | 0.1806 (7) | 0.2858 (8) | 0.035 (3) | |
H6A | 0.1546 | 0.2052 | 0.3415 | 0.042* | |
H6B | 0.2158 | 0.1675 | 0.2955 | 0.042* | |
C7 | 0.1202 (8) | 0.1043 (8) | 0.2695 (10) | 0.043 (4) | |
C8 | −0.0851 (11) | 0.0690 (10) | −0.0517 (12) | 0.084 (6) | |
H8A | −0.0841 | 0.0314 | −0.1000 | 0.127* | |
H8B | −0.1301 | 0.0985 | −0.0640 | 0.127* | |
H8C | −0.0818 | 0.0412 | 0.0054 | 0.127* | |
C9 | 0.1002 (9) | −0.0227 (8) | 0.3216 (10) | 0.061 (5) | |
H9A | 0.1198 | −0.0574 | 0.3714 | 0.092* | |
H9B | 0.1046 | −0.0475 | 0.2647 | 0.092* | |
H9C | 0.0496 | −0.0123 | 0.3225 | 0.092* | |
N1 | 0.0661 (5) | 0.2593 (5) | 0.1844 (6) | 0.028 (2) | |
H10 | 0.0402 | 0.2132 | 0.1833 | 0.033* | |
Hg1 | 0.3049 (5) | 0.0049 (5) | 0.5056 (10) | 0.090 (2) | 0.65 (3) |
Hg2 | 0.4016 (8) | 0.1094 (6) | 0.2486 (10) | 0.093 (3) | 0.35 (3) |
Hg1A | 0.2981 (7) | 0.0066 (8) | 0.4755 (17) | 0.080 (3) | 0.35 (3) |
Hg2A | 0.3863 (5) | 0.1011 (3) | 0.2299 (6) | 0.0817 (15) | 0.65 (3) |
I1 | 0.25297 (6) | −0.13689 (6) | 0.50906 (7) | 0.0627 (3) | |
I2 | 0.31927 (7) | 0.15598 (6) | 0.50683 (7) | 0.0689 (4) | |
I4 | 0.30375 (6) | −0.01951 (5) | 0.26976 (7) | 0.0566 (3) | |
I3 | 0.47111 (6) | −0.04490 (6) | 0.60649 (6) | 0.0479 (3) | |
I5 | 0.37510 (8) | 0.25573 (6) | 0.25774 (9) | 0.0741 (4) | |
O1 | −0.0239 (7) | 0.1233 (6) | −0.0461 (7) | 0.070 (3) | |
O2 | −0.0559 (6) | 0.1789 (5) | 0.0742 (7) | 0.056 (3) | |
O3 | 0.1397 (5) | 0.0500 (5) | 0.3308 (6) | 0.045 (2) | |
O4 | 0.0735 (7) | 0.0951 (6) | 0.2010 (8) | 0.078 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.028 (8) | 0.028 (6) | 0.032 (7) | 0.011 (5) | 0.005 (6) | −0.006 (5) |
C2 | 0.046 (10) | 0.047 (8) | 0.033 (8) | 0.007 (7) | 0.014 (7) | 0.008 (6) |
C3 | 0.037 (10) | 0.078 (10) | 0.040 (9) | 0.010 (8) | 0.015 (7) | 0.028 (8) |
C4 | 0.056 (11) | 0.047 (8) | 0.026 (8) | 0.015 (7) | 0.004 (7) | −0.003 (6) |
C5 | 0.016 (8) | 0.047 (8) | 0.050 (9) | −0.002 (6) | 0.005 (6) | −0.007 (6) |
C6 | 0.041 (9) | 0.036 (7) | 0.028 (7) | 0.002 (6) | 0.006 (6) | 0.000 (6) |
C7 | 0.031 (9) | 0.043 (8) | 0.055 (10) | 0.011 (7) | 0.007 (7) | −0.006 (7) |
C8 | 0.092 (10) | 0.078 (8) | 0.081 (9) | −0.016 (8) | 0.011 (8) | −0.008 (7) |
C9 | 0.064 (12) | 0.040 (8) | 0.079 (12) | 0.003 (8) | 0.007 (9) | 0.025 (8) |
N1 | 0.020 (6) | 0.031 (5) | 0.033 (6) | −0.005 (4) | 0.008 (5) | 0.000 (4) |
Hg1 | 0.081 (2) | 0.0364 (10) | 0.151 (5) | −0.0108 (13) | 0.015 (3) | −0.002 (2) |
Hg2 | 0.114 (4) | 0.041 (2) | 0.115 (4) | 0.021 (3) | 0.000 (5) | −0.016 (2) |
Hg1A | 0.051 (3) | 0.036 (2) | 0.150 (9) | −0.0001 (17) | 0.008 (4) | −0.016 (4) |
Hg2A | 0.116 (3) | 0.0442 (10) | 0.100 (2) | −0.0093 (16) | 0.060 (3) | −0.0169 (13) |
I1 | 0.0610 (8) | 0.0528 (6) | 0.0707 (8) | −0.0172 (5) | 0.0024 (6) | 0.0145 (5) |
I2 | 0.0921 (10) | 0.0360 (5) | 0.0640 (7) | −0.0001 (6) | −0.0235 (6) | −0.0057 (5) |
I4 | 0.0555 (8) | 0.0432 (5) | 0.0786 (8) | 0.0030 (5) | 0.0322 (6) | −0.0020 (5) |
I3 | 0.0445 (7) | 0.0608 (6) | 0.0398 (5) | −0.0005 (5) | 0.0118 (4) | 0.0052 (4) |
I5 | 0.0946 (11) | 0.0395 (6) | 0.0867 (9) | −0.0007 (6) | 0.0123 (7) | −0.0045 (5) |
O1 | 0.087 (10) | 0.083 (8) | 0.041 (6) | −0.014 (7) | 0.018 (6) | −0.014 (6) |
O2 | 0.057 (8) | 0.054 (6) | 0.055 (7) | −0.012 (5) | 0.008 (6) | −0.022 (5) |
O3 | 0.042 (7) | 0.037 (5) | 0.053 (6) | 0.014 (5) | 0.003 (5) | 0.007 (5) |
O4 | 0.101 (11) | 0.047 (6) | 0.068 (8) | −0.002 (6) | −0.031 (7) | 0.013 (5) |
Geometric parameters (Å, º) top
C1—N1 | 1.523 (13) | C8—H8B | 0.9600 |
C1—C1i | 1.54 (2) | C8—H8C | 0.9600 |
C1—H1A | 0.9700 | C9—O3 | 1.418 (16) |
C1—H1B | 0.9700 | C9—H9A | 0.9600 |
C2—N1 | 1.519 (14) | C9—H9B | 0.9600 |
C2—C3 | 1.533 (18) | C9—H9C | 0.9600 |
C2—H2A | 0.9700 | N1—H10 | 0.9100 |
C2—H2B | 0.9700 | Hg1—I2 | 2.553 (8) |
C3—C4 | 1.482 (19) | Hg1—I1 | 2.574 (8) |
C3—H3A | 0.9700 | Hg1—I3 | 3.283 (10) |
C3—H3B | 0.9700 | Hg1A—I2 | 2.570 (14) |
C4—O2 | 1.222 (15) | Hg1A—I1 | 2.631 (17) |
C4—O1 | 1.287 (15) | Hg1A—I4 | 3.11 (2) |
C5—C6 | 1.471 (16) | Hg2—I5 | 2.516 (9) |
C5—N1 | 1.542 (16) | Hg2—I3ii | 2.883 (9) |
C5—H5A | 0.9700 | Hg2—I4 | 2.883 (13) |
C5—H5B | 0.9700 | Hg2—I3iii | 3.086 (14) |
C6—C7 | 1.515 (17) | Hg2A—I5 | 2.645 (6) |
C6—H6A | 0.9700 | Hg2A—I4 | 2.673 (6) |
C6—H6B | 0.9700 | Hg2A—I3ii | 2.794 (4) |
C7—O4 | 1.220 (17) | Hg2A—I3iii | 3.383 (5) |
C7—O3 | 1.294 (15) | I3—Hg2Aiv | 2.794 (4) |
C8—O1 | 1.45 (2) | I3—Hg2iv | 2.883 (9) |
C8—H8A | 0.9600 | I3—Hg2iii | 3.086 (14) |
| | | |
N1—C1—C1i | 111.5 (10) | H8B—C8—H8C | 109.5 |
N1—C1—H1A | 109.3 | O3—C9—H9A | 109.5 |
C1i—C1—H1A | 109.3 | O3—C9—H9B | 109.5 |
N1—C1—H1B | 109.3 | H9A—C9—H9B | 109.5 |
C1i—C1—H1B | 109.3 | O3—C9—H9C | 109.5 |
H1A—C1—H1B | 108.0 | H9A—C9—H9C | 109.5 |
N1—C2—C3 | 112.0 (10) | H9B—C9—H9C | 109.5 |
N1—C2—H2A | 109.2 | C2—N1—C1 | 111.0 (9) |
C3—C2—H2A | 109.2 | C2—N1—C5 | 110.0 (9) |
N1—C2—H2B | 109.2 | C1—N1—C5 | 111.3 (9) |
C3—C2—H2B | 109.2 | C2—N1—H10 | 108.1 |
H2A—C2—H2B | 107.9 | C1—N1—H10 | 108.1 |
C4—C3—C2 | 110.8 (11) | C5—N1—H10 | 108.1 |
C4—C3—H3A | 109.5 | I2—Hg1—I1 | 163.6 (3) |
C2—C3—H3A | 109.5 | I2—Hg1—I3 | 99.3 (3) |
C4—C3—H3B | 109.5 | I1—Hg1—I3 | 94.6 (3) |
C2—C3—H3B | 109.5 | I2—Hg1a—I1 | 154.8 (10) |
H3A—C3—H3B | 108.1 | I2—Hg1a—I4 | 106.5 (8) |
O2—C4—O1 | 121.9 (14) | I1—Hg1a—I4 | 97.3 (5) |
O2—C4—C3 | 124.7 (12) | I5—Hg2—I3ii | 121.7 (3) |
O1—C4—C3 | 113.4 (12) | I5—Hg2—I4 | 126.5 (4) |
C6—C5—N1 | 113.1 (10) | I3ii—Hg2—I4 | 100.0 (4) |
C6—C5—H5A | 109.0 | I5—Hg2—I3iii | 116.0 (7) |
N1—C5—H5A | 109.0 | I3ii—Hg2—I3iii | 89.4 (3) |
C6—C5—H5B | 109.0 | I4—Hg2—I3iii | 94.4 (2) |
N1—C5—H5B | 109.0 | I5—Hg2a—I4 | 130.18 (15) |
H5A—C5—H5B | 107.8 | I5—Hg2a—I3ii | 120.32 (14) |
C5—C6—C7 | 114.6 (12) | I4—Hg2a—I3ii | 107.8 (2) |
C5—C6—H6A | 108.6 | I5—Hg2a—I3iii | 103.6 (2) |
C7—C6—H6A | 108.6 | I3ii—Hg2a—I3iii | 85.2 (2) |
C5—C6—H6B | 108.6 | I4—Hg2a—I3iii | 92.0 (2) |
C7—C6—H6B | 108.6 | Hg2a—I4—Hg1a | 103.6 (4) |
H6A—C6—H6B | 107.6 | Hg2—I4—Hg1a | 97.9 (4) |
O4—C7—O3 | 124.2 (13) | Hg2aiv—I3—Hg2iii | 82.8 (3) |
O4—C7—C6 | 121.3 (13) | Hg2iv—I3—Hg2iii | 75.3 (5) |
O3—C7—C6 | 114.3 (13) | Hg2aiv—I3—Hg1 | 77.8 (4) |
O1—C8—H8A | 109.5 | Hg2iv—I3—Hg1 | 85.4 (5) |
O1—C8—H8B | 109.5 | Hg2iii—I3—Hg1 | 160.6 (2) |
H8A—C8—H8B | 109.5 | C4—O1—C8 | 117.5 (12) |
O1—C8—H8C | 109.5 | C7—O3—C9 | 117.8 (12) |
H8A—C8—H8C | 109.5 | | |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y, z−1/2; (iii) −x+1, −y, −z+1; (iv) x, −y, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H10···O2 | 0.91 | 2.25 | 2.876 (14) | 125 |
N1—H10···O4 | 0.91 | 2.08 | 2.771 (13) | 132 |
C6—H6A···O2i | 0.97 | 2.44 | 3.150 (15) | 129 |
Symmetry code: (i) −x, y, −z+1/2. |