In the title compound, [Hg(C
40H
42N
4O
4)](PF
6)
2·CH
3NO
2, the geometry of the Hg coordination is distorted tetrahedral, formed by two C atoms [Hg—C = 2.076 (7) and 2.068 (7) Å] and two O atoms [Hg—O = 2.703 (5) and 2.934 (5) Å]. The crystal packing is stabilized by weak C—H
F and C—H
O interactions.
Supporting information
CCDC reference: 271852
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- R factor = 0.049
- wR factor = 0.112
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.81 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 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
4 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
{1,8-Bis[2-(1-benzyl-1
H-imidazol-3-ylmethyl-
κC2)phenoxy]-3,6-dioxaoctane-
κ2O3,
O6}mercury(II)
bis(hexaflourophosphate) nitromethane solvate
top
Crystal data top
[Hg(C40H42N4O4)](PF6)2·CH3NO2 | Z = 2 |
Mr = 1194.35 | F(000) = 1184 |
Triclinic, P1 | Dx = 1.706 Mg m−3 |
a = 10.729 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.116 (3) Å | Cell parameters from 932 reflections |
c = 19.552 (6) Å | θ = 2.3–22.3° |
α = 89.721 (5)° | µ = 3.48 mm−1 |
β = 85.328 (6)° | T = 293 K |
γ = 66.677 (4)° | Block, colourless |
V = 2325.1 (11) Å3 | 0.24 × 0.20 × 0.16 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 8170 independent reflections |
Radiation source: fine-focus sealed tube | 6318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→8 |
Tmin = 0.428, Tmax = 0.573 | k = −14→13 |
12192 measured reflections | l = −22→23 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3 |
8170 reflections | (Δ/σ)max = 0.001 |
605 parameters | Δρmax = 1.06 e Å−3 |
72 restraints | Δρmin = −0.91 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 | |
Hg1 | 0.23186 (3) | 0.25325 (2) | 0.270744 (15) | 0.04089 (11) | |
O1 | 0.4097 (5) | 0.0529 (5) | 0.3607 (3) | 0.0625 (16) | |
O2 | 0.5020 (5) | 0.1967 (5) | 0.2716 (3) | 0.0526 (13) | |
O3 | 0.3477 (5) | 0.4084 (5) | 0.1986 (3) | 0.0549 (14) | |
O4 | 0.0676 (6) | 0.4854 (5) | 0.1623 (3) | 0.0635 (16) | |
N1 | 0.1681 (6) | 0.2506 (6) | 0.4234 (3) | 0.0499 (16) | |
N2 | 0.2179 (6) | 0.4023 (5) | 0.4025 (3) | 0.0513 (17) | |
N3 | 0.1113 (6) | 0.2273 (5) | 0.1404 (3) | 0.0377 (13) | |
N4 | 0.3225 (6) | 0.1099 (5) | 0.1323 (3) | 0.0386 (14) | |
C1 | 0.2048 (7) | 0.3093 (6) | 0.3731 (4) | 0.0428 (18) | |
C2 | 0.1573 (10) | 0.3067 (9) | 0.4851 (5) | 0.074 (3) | |
H2 | 0.1331 | 0.2833 | 0.5278 | 0.088* | |
C3 | 0.1884 (10) | 0.4021 (9) | 0.4723 (4) | 0.073 (3) | |
H3 | 0.1897 | 0.4577 | 0.5045 | 0.088* | |
C4 | 0.1388 (8) | 0.1449 (7) | 0.4146 (5) | 0.057 (2) | |
H4A | 0.1297 | 0.1348 | 0.3663 | 0.069* | |
H4B | 0.0517 | 0.1587 | 0.4395 | 0.069* | |
C5 | 0.2438 (8) | 0.0296 (7) | 0.4383 (4) | 0.052 (2) | |
C6 | 0.2079 (10) | −0.0374 (9) | 0.4877 (5) | 0.073 (3) | |
H6 | 0.1204 | −0.0057 | 0.5098 | 0.087* | |
C7 | 0.2976 (13) | −0.1500 (10) | 0.5052 (6) | 0.083 (3) | |
H7 | 0.2712 | −0.1940 | 0.5381 | 0.099* | |
C8 | 0.4257 (14) | −0.1946 (9) | 0.4730 (6) | 0.091 (4) | |
H8 | 0.4870 | −0.2700 | 0.4846 | 0.109* | |
C9 | 0.4674 (10) | −0.1329 (8) | 0.4242 (5) | 0.074 (3) | |
H9 | 0.5551 | −0.1660 | 0.4025 | 0.088* | |
C10 | 0.3758 (9) | −0.0186 (7) | 0.4074 (4) | 0.055 (2) | |
C11 | 0.5502 (8) | 0.0304 (8) | 0.3449 (5) | 0.063 (2) | |
H11A | 0.5858 | −0.0231 | 0.3048 | 0.076* | |
H11B | 0.6015 | −0.0088 | 0.3831 | 0.076* | |
C12 | 0.5672 (8) | 0.1434 (8) | 0.3316 (4) | 0.061 (2) | |
H12A | 0.5276 | 0.1986 | 0.3707 | 0.073* | |
H12B | 0.6634 | 0.1276 | 0.3249 | 0.073* | |
C13 | 0.5509 (8) | 0.2854 (7) | 0.2470 (4) | 0.055 (2) | |
H13A | 0.6491 | 0.2487 | 0.2377 | 0.066* | |
H13B | 0.5287 | 0.3486 | 0.2818 | 0.066* | |
C14 | 0.4880 (8) | 0.3371 (8) | 0.1839 (4) | 0.061 (2) | |
H14A | 0.5330 | 0.3860 | 0.1632 | 0.073* | |
H14B | 0.4996 | 0.2728 | 0.1514 | 0.073* | |
C15 | 0.2944 (9) | 0.4701 (9) | 0.1382 (5) | 0.078 (3) | |
H15A | 0.3041 | 0.4115 | 0.1023 | 0.094* | |
H15B | 0.3473 | 0.5156 | 0.1223 | 0.094* | |
C16 | 0.1507 (9) | 0.5519 (7) | 0.1500 (5) | 0.070 (3) | |
H16A | 0.1387 | 0.6049 | 0.1892 | 0.084* | |
H16B | 0.1232 | 0.6010 | 0.1102 | 0.084* | |
C17 | −0.0422 (7) | 0.5054 (6) | 0.1238 (4) | 0.0470 (19) | |
C18 | −0.1033 (9) | 0.6069 (7) | 0.0874 (5) | 0.065 (2) | |
H18 | −0.0725 | 0.6686 | 0.0868 | 0.078* | |
C19 | −0.2128 (9) | 0.6144 (8) | 0.0515 (5) | 0.074 (3) | |
H19 | −0.2546 | 0.6821 | 0.0260 | 0.089* | |
C20 | −0.2605 (9) | 0.5264 (8) | 0.0523 (5) | 0.068 (2) | |
H20 | −0.3338 | 0.5332 | 0.0278 | 0.081* | |
C21 | −0.1989 (8) | 0.4276 (7) | 0.0899 (4) | 0.055 (2) | |
H21 | −0.2309 | 0.3666 | 0.0906 | 0.065* | |
C22 | −0.0911 (7) | 0.4154 (6) | 0.1269 (4) | 0.0421 (17) | |
C23 | −0.0263 (7) | 0.3072 (6) | 0.1691 (4) | 0.0447 (18) | |
H23A | −0.0210 | 0.3335 | 0.2151 | 0.054* | |
H23B | −0.0838 | 0.2622 | 0.1725 | 0.054* | |
C24 | 0.2242 (7) | 0.1899 (6) | 0.1738 (3) | 0.0362 (16) | |
C25 | 0.2720 (8) | 0.0991 (7) | 0.0715 (4) | 0.0477 (19) | |
H25 | 0.3202 | 0.0501 | 0.0337 | 0.057* | |
C26 | 0.1413 (8) | 0.1720 (6) | 0.0771 (4) | 0.0468 (19) | |
H26 | 0.0807 | 0.1835 | 0.0438 | 0.056* | |
C27 | 0.2582 (8) | 0.4918 (7) | 0.3678 (5) | 0.062 (2) | |
H27A | 0.2991 | 0.4612 | 0.3220 | 0.075* | |
H27B | 0.3267 | 0.5037 | 0.3927 | 0.075* | |
C28 | 0.1409 (8) | 0.6106 (7) | 0.3624 (4) | 0.0505 (19) | |
C29 | 0.0233 (10) | 0.6195 (9) | 0.3352 (5) | 0.078 (3) | |
H29 | 0.0114 | 0.5499 | 0.3242 | 0.093* | |
C30 | −0.0782 (10) | 0.7311 (11) | 0.3240 (5) | 0.084 (3) | |
H30 | −0.1566 | 0.7359 | 0.3047 | 0.101* | |
C31 | −0.0626 (12) | 0.8335 (9) | 0.3412 (6) | 0.082 (3) | |
H31 | −0.1304 | 0.9085 | 0.3343 | 0.098* | |
C32 | 0.0510 (12) | 0.8250 (8) | 0.3681 (6) | 0.087 (3) | |
H32 | 0.0618 | 0.8950 | 0.3792 | 0.105* | |
C33 | 0.1522 (9) | 0.7161 (7) | 0.3799 (5) | 0.064 (2) | |
H33 | 0.2291 | 0.7134 | 0.3998 | 0.076* | |
C34 | 0.4552 (7) | 0.0279 (6) | 0.1517 (4) | 0.0484 (19) | |
H34A | 0.4867 | 0.0688 | 0.1845 | 0.058* | |
H34B | 0.5199 | 0.0063 | 0.1114 | 0.058* | |
C35 | 0.4521 (8) | −0.0854 (6) | 0.1829 (4) | 0.0456 (18) | |
C36 | 0.3335 (9) | −0.0986 (8) | 0.2047 (5) | 0.069 (3) | |
H36 | 0.2504 | −0.0353 | 0.1995 | 0.082* | |
C37 | 0.3341 (11) | −0.2019 (9) | 0.2337 (6) | 0.094 (4) | |
H37 | 0.2528 | −0.2087 | 0.2482 | 0.113* | |
C38 | 0.4583 (14) | −0.2960 (9) | 0.2409 (6) | 0.100 (4) | |
H38 | 0.4605 | −0.3662 | 0.2614 | 0.120* | |
C39 | 0.5760 (12) | −0.2869 (9) | 0.2185 (7) | 0.096 (4) | |
H39 | 0.6588 | −0.3510 | 0.2229 | 0.115* | |
C40 | 0.5736 (9) | −0.1824 (8) | 0.1889 (5) | 0.074 (3) | |
H40 | 0.6551 | −0.1773 | 0.1729 | 0.089* | |
P1 | 0.8775 (2) | 0.9848 (2) | 0.13698 (14) | 0.0616 (6) | |
P2 | 0.7617 (2) | 0.4098 (2) | 0.36420 (12) | 0.0606 (6) | |
F1 | 0.9688 (8) | 1.0034 (9) | 0.0770 (5) | 0.183 (4) | |
F2 | 0.9777 (9) | 0.8579 (6) | 0.1504 (5) | 0.159 (3) | |
F3 | 0.8039 (10) | 0.9424 (8) | 0.0866 (5) | 0.168 (3) | |
F4 | 0.7805 (8) | 0.9754 (8) | 0.1966 (4) | 0.148 (3) | |
F5 | 0.7765 (8) | 1.1171 (6) | 0.1251 (4) | 0.144 (3) | |
F6 | 0.9470 (11) | 1.0315 (9) | 0.1868 (6) | 0.196 (4) | |
F7 | 0.8109 (7) | 0.3747 (5) | 0.4382 (3) | 0.109 (2) | |
F8 | 0.8042 (7) | 0.2722 (5) | 0.3467 (3) | 0.1023 (19) | |
F9 | 0.6161 (7) | 0.4205 (8) | 0.3892 (4) | 0.135 (3) | |
F10 | 0.7228 (6) | 0.4387 (5) | 0.2888 (3) | 0.0891 (17) | |
F11 | 0.7225 (7) | 0.5469 (5) | 0.3820 (3) | 0.1024 (19) | |
F12 | 0.9124 (6) | 0.3924 (7) | 0.3404 (4) | 0.122 (2) | |
C41 | 0.2523 (10) | 0.8121 (9) | 0.0396 (5) | 0.085 (3) | |
H41A | 0.1999 | 0.7696 | 0.0250 | 0.128* | |
H41B | 0.2109 | 0.8947 | 0.0272 | 0.128* | |
H41C | 0.2553 | 0.8078 | 0.0885 | 0.128* | |
N5 | 0.3909 (8) | 0.7575 (7) | 0.0064 (4) | 0.066 (2) | |
O5 | 0.4576 (7) | 0.8191 (7) | −0.0009 (4) | 0.093 (2) | |
O6 | 0.4326 (7) | 0.6541 (6) | −0.0140 (4) | 0.107 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.04394 (18) | 0.04093 (17) | 0.03643 (17) | −0.01413 (12) | −0.00995 (11) | −0.00259 (11) |
O1 | 0.044 (3) | 0.063 (4) | 0.064 (4) | −0.004 (3) | −0.001 (3) | 0.022 (3) |
O2 | 0.043 (3) | 0.068 (4) | 0.052 (3) | −0.026 (3) | −0.012 (3) | 0.006 (3) |
O3 | 0.052 (3) | 0.058 (3) | 0.059 (4) | −0.026 (3) | −0.013 (3) | 0.013 (3) |
O4 | 0.061 (4) | 0.061 (4) | 0.085 (4) | −0.037 (3) | −0.032 (3) | 0.025 (3) |
N1 | 0.051 (4) | 0.053 (4) | 0.035 (4) | −0.009 (3) | −0.003 (3) | −0.006 (3) |
N2 | 0.057 (4) | 0.045 (4) | 0.048 (4) | −0.015 (3) | −0.013 (3) | −0.010 (3) |
N3 | 0.042 (4) | 0.034 (3) | 0.037 (3) | −0.015 (3) | −0.007 (3) | 0.004 (3) |
N4 | 0.044 (4) | 0.029 (3) | 0.043 (4) | −0.015 (3) | −0.007 (3) | 0.000 (3) |
C1 | 0.042 (4) | 0.040 (4) | 0.038 (4) | −0.006 (3) | −0.012 (3) | −0.003 (3) |
C2 | 0.086 (7) | 0.075 (7) | 0.041 (5) | −0.012 (5) | 0.001 (5) | −0.004 (5) |
C3 | 0.098 (8) | 0.069 (6) | 0.038 (5) | −0.014 (6) | −0.015 (5) | −0.016 (5) |
C4 | 0.048 (5) | 0.062 (5) | 0.064 (6) | −0.023 (4) | −0.010 (4) | 0.011 (4) |
C5 | 0.058 (5) | 0.051 (5) | 0.053 (5) | −0.026 (4) | −0.012 (4) | 0.008 (4) |
C6 | 0.083 (7) | 0.092 (7) | 0.061 (6) | −0.053 (6) | −0.013 (5) | 0.014 (5) |
C7 | 0.116 (9) | 0.085 (8) | 0.073 (7) | −0.064 (7) | −0.033 (7) | 0.036 (6) |
C8 | 0.129 (11) | 0.058 (6) | 0.093 (9) | −0.038 (7) | −0.046 (8) | 0.033 (6) |
C9 | 0.061 (6) | 0.070 (6) | 0.079 (7) | −0.012 (5) | −0.019 (5) | 0.013 (5) |
C10 | 0.066 (6) | 0.054 (5) | 0.046 (5) | −0.022 (4) | −0.019 (4) | 0.012 (4) |
C11 | 0.039 (5) | 0.077 (6) | 0.057 (6) | −0.005 (4) | −0.011 (4) | 0.013 (5) |
C12 | 0.046 (5) | 0.076 (6) | 0.060 (6) | −0.021 (4) | −0.019 (4) | 0.006 (5) |
C13 | 0.036 (4) | 0.061 (5) | 0.068 (6) | −0.021 (4) | 0.000 (4) | −0.012 (4) |
C14 | 0.059 (6) | 0.064 (5) | 0.063 (6) | −0.028 (5) | 0.000 (4) | 0.006 (5) |
C15 | 0.070 (7) | 0.083 (7) | 0.088 (8) | −0.035 (6) | −0.015 (5) | 0.037 (6) |
C16 | 0.071 (6) | 0.055 (5) | 0.094 (8) | −0.033 (5) | −0.027 (5) | 0.029 (5) |
C17 | 0.040 (4) | 0.040 (4) | 0.056 (5) | −0.008 (3) | −0.010 (4) | −0.001 (4) |
C18 | 0.060 (6) | 0.044 (5) | 0.093 (7) | −0.020 (4) | −0.023 (5) | 0.022 (5) |
C19 | 0.068 (6) | 0.066 (6) | 0.074 (7) | −0.009 (5) | −0.026 (5) | 0.030 (5) |
C20 | 0.059 (6) | 0.079 (6) | 0.068 (6) | −0.027 (5) | −0.026 (5) | 0.013 (5) |
C21 | 0.057 (5) | 0.059 (5) | 0.049 (5) | −0.021 (4) | −0.015 (4) | 0.004 (4) |
C22 | 0.036 (4) | 0.040 (4) | 0.046 (5) | −0.011 (3) | −0.008 (3) | 0.003 (3) |
C23 | 0.041 (4) | 0.049 (4) | 0.043 (5) | −0.017 (4) | −0.005 (3) | 0.004 (4) |
C24 | 0.044 (4) | 0.032 (4) | 0.037 (4) | −0.019 (3) | −0.009 (3) | 0.003 (3) |
C25 | 0.060 (5) | 0.043 (4) | 0.039 (5) | −0.020 (4) | −0.003 (4) | −0.008 (4) |
C26 | 0.062 (5) | 0.049 (4) | 0.033 (4) | −0.023 (4) | −0.015 (4) | 0.003 (3) |
C27 | 0.053 (5) | 0.048 (5) | 0.082 (7) | −0.015 (4) | −0.009 (4) | −0.019 (5) |
C28 | 0.051 (5) | 0.053 (5) | 0.044 (5) | −0.017 (4) | −0.007 (4) | −0.007 (4) |
C29 | 0.075 (7) | 0.070 (6) | 0.090 (8) | −0.028 (5) | −0.024 (6) | −0.017 (5) |
C30 | 0.064 (7) | 0.104 (9) | 0.069 (7) | −0.015 (6) | −0.017 (5) | −0.001 (6) |
C31 | 0.084 (8) | 0.054 (6) | 0.083 (8) | −0.005 (5) | 0.004 (6) | 0.013 (5) |
C32 | 0.095 (9) | 0.049 (6) | 0.118 (10) | −0.029 (6) | −0.002 (7) | 0.000 (6) |
C33 | 0.064 (6) | 0.059 (6) | 0.074 (6) | −0.032 (5) | −0.001 (5) | −0.010 (5) |
C34 | 0.043 (4) | 0.040 (4) | 0.057 (5) | −0.012 (3) | −0.006 (4) | −0.003 (4) |
C35 | 0.046 (5) | 0.038 (4) | 0.051 (5) | −0.015 (4) | −0.005 (4) | −0.002 (3) |
C36 | 0.056 (6) | 0.058 (6) | 0.083 (7) | −0.014 (4) | −0.002 (5) | 0.014 (5) |
C37 | 0.094 (8) | 0.077 (7) | 0.115 (10) | −0.040 (7) | 0.005 (7) | 0.031 (7) |
C38 | 0.130 (11) | 0.056 (6) | 0.107 (10) | −0.029 (7) | −0.004 (8) | 0.035 (6) |
C39 | 0.086 (8) | 0.052 (6) | 0.132 (11) | −0.007 (6) | −0.014 (7) | 0.029 (6) |
C40 | 0.058 (6) | 0.058 (6) | 0.093 (8) | −0.009 (5) | −0.004 (5) | 0.006 (5) |
P1 | 0.0519 (14) | 0.0564 (14) | 0.0766 (17) | −0.0233 (11) | 0.0049 (12) | −0.0007 (12) |
P2 | 0.0669 (16) | 0.0722 (15) | 0.0567 (15) | −0.0395 (13) | −0.0209 (12) | 0.0078 (12) |
F1 | 0.132 (6) | 0.217 (7) | 0.180 (7) | −0.060 (5) | 0.048 (5) | 0.057 (6) |
F2 | 0.159 (6) | 0.092 (5) | 0.173 (7) | 0.002 (4) | 0.007 (5) | 0.019 (5) |
F3 | 0.223 (7) | 0.186 (7) | 0.139 (6) | −0.120 (6) | −0.057 (5) | −0.011 (5) |
F4 | 0.116 (5) | 0.207 (7) | 0.119 (5) | −0.067 (5) | 0.017 (4) | 0.040 (5) |
F5 | 0.145 (6) | 0.098 (5) | 0.133 (6) | 0.011 (4) | −0.007 (5) | 0.010 (4) |
F6 | 0.228 (8) | 0.193 (7) | 0.227 (8) | −0.130 (6) | −0.108 (6) | 0.016 (6) |
F7 | 0.160 (5) | 0.104 (4) | 0.073 (4) | −0.057 (4) | −0.045 (4) | 0.006 (3) |
F8 | 0.148 (5) | 0.077 (4) | 0.092 (4) | −0.051 (3) | −0.037 (4) | 0.005 (3) |
F9 | 0.096 (5) | 0.192 (6) | 0.129 (6) | −0.074 (5) | 0.018 (4) | −0.018 (5) |
F10 | 0.114 (4) | 0.095 (4) | 0.062 (3) | −0.040 (3) | −0.036 (3) | 0.018 (3) |
F11 | 0.132 (5) | 0.071 (3) | 0.097 (4) | −0.029 (3) | −0.032 (4) | −0.003 (3) |
F12 | 0.084 (4) | 0.155 (5) | 0.145 (6) | −0.065 (4) | −0.019 (4) | 0.010 (5) |
C41 | 0.080 (7) | 0.080 (7) | 0.088 (8) | −0.029 (6) | 0.019 (6) | −0.023 (6) |
N5 | 0.062 (5) | 0.065 (5) | 0.063 (5) | −0.015 (4) | −0.015 (4) | −0.005 (4) |
O5 | 0.073 (5) | 0.099 (5) | 0.108 (6) | −0.038 (4) | −0.002 (4) | −0.005 (5) |
O6 | 0.087 (5) | 0.070 (5) | 0.136 (7) | 0.002 (4) | −0.025 (5) | −0.032 (5) |
Geometric parameters (Å, º) top
Hg1—C24 | 2.068 (7) | C19—C20 | 1.353 (12) |
Hg1—C1 | 2.076 (7) | C19—H19 | 0.9300 |
Hg1—O2 | 2.703 (5) | C20—C21 | 1.361 (11) |
Hg1—O3 | 2.934 (5) | C20—H20 | 0.9300 |
O1—C10 | 1.379 (9) | C21—C22 | 1.373 (10) |
O1—C11 | 1.430 (9) | C21—H21 | 0.9300 |
O2—C12 | 1.432 (9) | C22—C23 | 1.497 (9) |
O2—C13 | 1.435 (9) | C23—H23A | 0.9700 |
O3—C14 | 1.414 (9) | C23—H23B | 0.9700 |
O3—C15 | 1.429 (10) | C25—C26 | 1.325 (10) |
O4—C17 | 1.390 (8) | C25—H25 | 0.9300 |
O4—C16 | 1.426 (9) | C26—H26 | 0.9300 |
N1—C1 | 1.334 (9) | C27—C28 | 1.502 (10) |
N1—C2 | 1.361 (10) | C27—H27A | 0.9700 |
N1—C4 | 1.449 (10) | C27—H27B | 0.9700 |
N2—C1 | 1.329 (9) | C28—C29 | 1.373 (11) |
N2—C3 | 1.375 (10) | C28—C33 | 1.378 (11) |
N2—C27 | 1.463 (10) | C29—C30 | 1.391 (13) |
N3—C24 | 1.338 (8) | C29—H29 | 0.9300 |
N3—C26 | 1.362 (9) | C30—C31 | 1.364 (14) |
N3—C23 | 1.473 (9) | C30—H30 | 0.9300 |
N4—C24 | 1.331 (9) | C31—C32 | 1.332 (14) |
N4—C25 | 1.374 (9) | C31—H31 | 0.9300 |
N4—C34 | 1.457 (8) | C32—C33 | 1.369 (12) |
C2—C3 | 1.342 (13) | C32—H32 | 0.9300 |
C2—H2 | 0.9300 | C33—H33 | 0.9300 |
C3—H3 | 0.9300 | C34—C35 | 1.510 (10) |
C4—C5 | 1.506 (10) | C34—H34A | 0.9700 |
C4—H4A | 0.9700 | C34—H34B | 0.9700 |
C4—H4B | 0.9700 | C35—C36 | 1.378 (11) |
C5—C10 | 1.386 (12) | C35—C40 | 1.380 (11) |
C5—C6 | 1.386 (12) | C36—C37 | 1.369 (12) |
C6—C7 | 1.384 (13) | C36—H36 | 0.9300 |
C6—H6 | 0.9300 | C37—C38 | 1.387 (14) |
C7—C8 | 1.361 (15) | C37—H37 | 0.9300 |
C7—H7 | 0.9300 | C38—C39 | 1.348 (15) |
C8—C9 | 1.362 (14) | C38—H38 | 0.9300 |
C8—H8 | 0.9300 | C39—C40 | 1.381 (13) |
C9—C10 | 1.401 (11) | C39—H39 | 0.9300 |
C9—H9 | 0.9300 | C40—H40 | 0.9300 |
C11—C12 | 1.471 (11) | P1—F6 | 1.511 (8) |
C11—H11A | 0.9700 | P1—F3 | 1.520 (8) |
C11—H11B | 0.9700 | P1—F2 | 1.523 (7) |
C12—H12A | 0.9700 | P1—F4 | 1.533 (7) |
C12—H12B | 0.9700 | P1—F1 | 1.540 (8) |
C13—C14 | 1.469 (11) | P1—F5 | 1.569 (7) |
C13—H13A | 0.9700 | P2—F9 | 1.553 (7) |
C13—H13B | 0.9700 | P2—F10 | 1.565 (5) |
C14—H14A | 0.9700 | P2—F8 | 1.575 (6) |
C14—H14B | 0.9700 | P2—F11 | 1.576 (6) |
C15—C16 | 1.465 (12) | P2—F12 | 1.576 (7) |
C15—H15A | 0.9700 | P2—F7 | 1.579 (6) |
C15—H15B | 0.9700 | C41—N5 | 1.462 (11) |
C16—H16A | 0.9700 | C41—H41A | 0.9600 |
C16—H16B | 0.9700 | C41—H41B | 0.9600 |
C17—C18 | 1.370 (10) | C41—H41C | 0.9600 |
C17—C22 | 1.383 (10) | N5—O6 | 1.209 (9) |
C18—C19 | 1.389 (11) | N5—O5 | 1.223 (9) |
C18—H18 | 0.9300 | | |
| | | |
C24—Hg1—C1 | 168.3 (3) | C21—C22—C17 | 118.2 (7) |
O2—Hg1—O3 | 61.5 (2) | C21—C22—C23 | 121.2 (7) |
C1—Hg1—O2 | 89.5 (2) | C17—C22—C23 | 120.5 (6) |
C24—Hg1—O2 | 100.8 (2) | N3—C23—C22 | 113.1 (6) |
C1—Hg1—O3 | 104.6 (2) | N3—C23—H23A | 109.0 |
C24—Hg1—O3 | 85.3 (2) | C22—C23—H23A | 109.0 |
C10—O1—C11 | 118.8 (6) | N3—C23—H23B | 109.0 |
C12—O2—C13 | 109.8 (6) | C22—C23—H23B | 109.0 |
C14—O3—C15 | 108.9 (6) | H23A—C23—H23B | 107.8 |
C17—O4—C16 | 120.3 (6) | N4—C24—N3 | 106.5 (6) |
C1—N1—C2 | 110.2 (7) | N4—C24—Hg1 | 129.8 (5) |
C1—N1—C4 | 125.7 (7) | N3—C24—Hg1 | 123.6 (5) |
C2—N1—C4 | 124.0 (8) | C26—C25—N4 | 106.6 (7) |
C1—N2—C3 | 109.3 (7) | C26—C25—H25 | 126.7 |
C1—N2—C27 | 126.5 (7) | N4—C25—H25 | 126.7 |
C3—N2—C27 | 124.2 (7) | C25—C26—N3 | 108.0 (6) |
C24—N3—C26 | 109.1 (6) | C25—C26—H26 | 126.0 |
C24—N3—C23 | 125.8 (6) | N3—C26—H26 | 126.0 |
C26—N3—C23 | 124.9 (6) | N2—C27—C28 | 112.9 (7) |
C24—N4—C25 | 109.6 (6) | N2—C27—H27A | 109.0 |
C24—N4—C34 | 125.9 (6) | C28—C27—H27A | 109.0 |
C25—N4—C34 | 123.4 (6) | N2—C27—H27B | 109.0 |
N2—C1—N1 | 106.7 (7) | C28—C27—H27B | 109.0 |
N2—C1—Hg1 | 130.9 (6) | H27A—C27—H27B | 107.8 |
N1—C1—Hg1 | 122.4 (5) | C29—C28—C33 | 117.5 (8) |
C3—C2—N1 | 106.6 (8) | C29—C28—C27 | 121.8 (7) |
C3—C2—H2 | 126.7 | C33—C28—C27 | 120.5 (7) |
N1—C2—H2 | 126.7 | C28—C29—C30 | 120.9 (9) |
C2—C3—N2 | 107.2 (8) | C28—C29—H29 | 119.5 |
C2—C3—H3 | 126.4 | C30—C29—H29 | 119.5 |
N2—C3—H3 | 126.4 | C31—C30—C29 | 119.8 (10) |
N1—C4—C5 | 115.2 (6) | C31—C30—H30 | 120.1 |
N1—C4—H4A | 108.5 | C29—C30—H30 | 120.1 |
C5—C4—H4A | 108.5 | C32—C31—C30 | 119.3 (9) |
N1—C4—H4B | 108.5 | C32—C31—H31 | 120.4 |
C5—C4—H4B | 108.5 | C30—C31—H31 | 120.4 |
H4A—C4—H4B | 107.5 | C31—C32—C33 | 122.0 (9) |
C10—C5—C6 | 117.6 (8) | C31—C32—H32 | 119.0 |
C10—C5—C4 | 121.4 (7) | C33—C32—H32 | 119.0 |
C6—C5—C4 | 120.7 (8) | C32—C33—C28 | 120.5 (9) |
C7—C6—C5 | 122.3 (10) | C32—C33—H33 | 119.7 |
C7—C6—H6 | 118.9 | C28—C33—H33 | 119.7 |
C5—C6—H6 | 118.9 | N4—C34—C35 | 112.8 (6) |
C8—C7—C6 | 118.1 (9) | N4—C34—H34A | 109.0 |
C8—C7—H7 | 120.9 | C35—C34—H34A | 109.0 |
C6—C7—H7 | 120.9 | N4—C34—H34B | 109.0 |
C7—C8—C9 | 122.4 (10) | C35—C34—H34B | 109.0 |
C7—C8—H8 | 118.8 | H34A—C34—H34B | 107.8 |
C9—C8—H8 | 118.8 | C36—C35—C40 | 117.6 (8) |
C8—C9—C10 | 118.8 (10) | C36—C35—C34 | 123.5 (7) |
C8—C9—H9 | 120.6 | C40—C35—C34 | 118.9 (7) |
C10—C9—H9 | 120.6 | C37—C36—C35 | 122.1 (8) |
O1—C10—C5 | 116.0 (7) | C37—C36—H36 | 119.0 |
O1—C10—C9 | 123.3 (8) | C35—C36—H36 | 119.0 |
C5—C10—C9 | 120.7 (8) | C36—C37—C38 | 118.6 (10) |
O1—C11—C12 | 110.7 (7) | C36—C37—H37 | 120.7 |
O1—C11—H11A | 109.5 | C38—C37—H37 | 120.7 |
C12—C11—H11A | 109.5 | C39—C38—C37 | 120.6 (10) |
O1—C11—H11B | 109.5 | C39—C38—H38 | 119.7 |
C12—C11—H11B | 109.5 | C37—C38—H38 | 119.7 |
H11A—C11—H11B | 108.1 | C38—C39—C40 | 120.0 (10) |
O2—C12—C11 | 110.0 (7) | C38—C39—H39 | 120.0 |
O2—C12—H12A | 109.7 | C40—C39—H39 | 120.0 |
C11—C12—H12A | 109.7 | C35—C40—C39 | 121.0 (9) |
O2—C12—H12B | 109.7 | C35—C40—H40 | 119.5 |
C11—C12—H12B | 109.7 | C39—C40—H40 | 119.5 |
H12A—C12—H12B | 108.2 | F6—P1—F3 | 177.9 (6) |
O2—C13—C14 | 110.0 (6) | F6—P1—F2 | 88.3 (6) |
O2—C13—H13A | 109.7 | F3—P1—F2 | 93.8 (5) |
C14—C13—H13A | 109.7 | F6—P1—F4 | 89.5 (6) |
O2—C13—H13B | 109.7 | F3—P1—F4 | 90.4 (5) |
C14—C13—H13B | 109.7 | F2—P1—F4 | 89.6 (5) |
H13A—C13—H13B | 108.2 | F6—P1—F1 | 89.9 (6) |
O3—C14—C13 | 110.6 (7) | F3—P1—F1 | 90.1 (6) |
O3—C14—H14A | 109.5 | F2—P1—F1 | 94.3 (5) |
C13—C14—H14A | 109.5 | F4—P1—F1 | 176.1 (5) |
O3—C14—H14B | 109.5 | F6—P1—F5 | 89.8 (5) |
C13—C14—H14B | 109.5 | F3—P1—F5 | 88.2 (5) |
H14A—C14—H14B | 108.1 | F2—P1—F5 | 178.0 (6) |
O3—C15—C16 | 112.5 (8) | F4—P1—F5 | 90.3 (5) |
O3—C15—H15A | 109.1 | F1—P1—F5 | 85.8 (5) |
C16—C15—H15A | 109.1 | F9—P2—F10 | 92.1 (4) |
O3—C15—H15B | 109.1 | F9—P2—F8 | 89.6 (4) |
C16—C15—H15B | 109.1 | F10—P2—F8 | 89.1 (3) |
H15A—C15—H15B | 107.8 | F9—P2—F11 | 91.5 (4) |
O4—C16—C15 | 110.4 (7) | F10—P2—F11 | 91.4 (3) |
O4—C16—H16A | 109.6 | F8—P2—F11 | 178.7 (4) |
C15—C16—H16A | 109.6 | F9—P2—F12 | 177.0 (4) |
O4—C16—H16B | 109.6 | F10—P2—F12 | 89.6 (4) |
C15—C16—H16B | 109.6 | F8—P2—F12 | 88.0 (4) |
H16A—C16—H16B | 108.1 | F11—P2—F12 | 90.8 (4) |
C18—C17—C22 | 121.2 (7) | F9—P2—F7 | 91.0 (4) |
C18—C17—O4 | 124.3 (7) | F10—P2—F7 | 176.1 (4) |
C22—C17—O4 | 114.5 (6) | F8—P2—F7 | 88.6 (3) |
C17—C18—C19 | 117.8 (8) | F11—P2—F7 | 90.7 (3) |
C17—C18—H18 | 121.1 | F12—P2—F7 | 87.1 (4) |
C19—C18—H18 | 121.1 | N5—C41—H41A | 109.5 |
C20—C19—C18 | 122.2 (8) | N5—C41—H41B | 109.5 |
C20—C19—H19 | 118.9 | H41A—C41—H41B | 109.5 |
C18—C19—H19 | 118.9 | N5—C41—H41C | 109.5 |
C19—C20—C21 | 118.5 (8) | H41A—C41—H41C | 109.5 |
C19—C20—H20 | 120.7 | H41B—C41—H41C | 109.5 |
C21—C20—H20 | 120.7 | O6—N5—O5 | 123.2 (9) |
C20—C21—C22 | 122.0 (8) | O6—N5—C41 | 118.1 (9) |
C20—C21—H21 | 119.0 | O5—N5—C41 | 118.7 (8) |
C22—C21—H21 | 119.0 | | |
| | | |
C3—N2—C1—N1 | −0.3 (8) | C20—C21—C22—C23 | 178.8 (8) |
C27—N2—C1—N1 | 179.3 (6) | C18—C17—C22—C21 | 2.9 (12) |
C3—N2—C1—Hg1 | 179.8 (6) | O4—C17—C22—C21 | −179.5 (7) |
C27—N2—C1—Hg1 | −0.7 (11) | C18—C17—C22—C23 | −177.7 (8) |
C2—N1—C1—N2 | 0.2 (8) | O4—C17—C22—C23 | −0.2 (10) |
C4—N1—C1—N2 | 178.3 (6) | C24—N3—C23—C22 | 125.7 (7) |
C2—N1—C1—Hg1 | −179.8 (5) | C26—N3—C23—C22 | −60.0 (9) |
C4—N1—C1—Hg1 | −1.8 (10) | C21—C22—C23—N3 | 109.7 (8) |
C24—Hg1—C1—N2 | −140.2 (12) | C17—C22—C23—N3 | −69.6 (9) |
C24—Hg1—C1—N1 | 39.9 (16) | C25—N4—C24—N3 | 1.6 (7) |
C1—N1—C2—C3 | −0.1 (10) | C34—N4—C24—N3 | −166.9 (6) |
C4—N1—C2—C3 | −178.2 (7) | C25—N4—C24—Hg1 | −177.5 (5) |
N1—C2—C3—N2 | −0.1 (10) | C34—N4—C24—Hg1 | 14.0 (10) |
C1—N2—C3—C2 | 0.2 (10) | C26—N3—C24—N4 | −1.5 (7) |
C27—N2—C3—C2 | −179.4 (7) | C23—N3—C24—N4 | 173.5 (6) |
C1—N1—C4—C5 | 108.7 (9) | C26—N3—C24—Hg1 | 177.7 (5) |
C2—N1—C4—C5 | −73.5 (10) | C23—N3—C24—Hg1 | −7.3 (9) |
N1—C4—C5—C10 | −63.8 (11) | C1—Hg1—C24—N4 | −131.3 (12) |
N1—C4—C5—C6 | 122.2 (9) | C1—Hg1—C24—N3 | 49.7 (15) |
C10—C5—C6—C7 | −1.6 (14) | C24—N4—C25—C26 | −1.1 (8) |
C4—C5—C6—C7 | 172.6 (8) | C34—N4—C25—C26 | 167.8 (6) |
C5—C6—C7—C8 | 0.7 (15) | N4—C25—C26—N3 | 0.1 (8) |
C6—C7—C8—C9 | −0.4 (17) | C24—N3—C26—C25 | 0.9 (8) |
C7—C8—C9—C10 | 1.0 (16) | C23—N3—C26—C25 | −174.2 (6) |
C11—O1—C10—C5 | 158.7 (7) | C1—N2—C27—C28 | 105.1 (8) |
C11—O1—C10—C9 | −20.7 (12) | C3—N2—C27—C28 | −75.4 (10) |
C6—C5—C10—O1 | −177.3 (7) | N2—C27—C28—C29 | −52.6 (11) |
C4—C5—C10—O1 | 8.5 (11) | N2—C27—C28—C33 | 132.5 (8) |
C6—C5—C10—C9 | 2.1 (13) | C33—C28—C29—C30 | 1.9 (14) |
C4—C5—C10—C9 | −172.0 (8) | C27—C28—C29—C30 | −173.1 (9) |
C8—C9—C10—O1 | 177.5 (9) | C28—C29—C30—C31 | −1.2 (16) |
C8—C9—C10—C5 | −1.8 (14) | C29—C30—C31—C32 | 0.7 (17) |
C10—O1—C11—C12 | −145.9 (7) | C30—C31—C32—C33 | −0.9 (17) |
C13—O2—C12—C11 | −163.2 (7) | C31—C32—C33—C28 | 1.7 (17) |
O1—C11—C12—O2 | −64.3 (9) | C29—C28—C33—C32 | −2.1 (14) |
C12—O2—C13—C14 | 177.9 (7) | C27—C28—C33—C32 | 173.0 (9) |
C15—O3—C14—C13 | 172.1 (7) | C24—N4—C34—C35 | 84.0 (8) |
O2—C13—C14—O3 | 69.3 (8) | C25—N4—C34—C35 | −83.0 (9) |
C14—O3—C15—C16 | −176.6 (7) | N4—C34—C35—C36 | −13.5 (11) |
C17—O4—C16—C15 | −126.7 (8) | N4—C34—C35—C40 | 165.0 (7) |
O3—C15—C16—O4 | −68.4 (10) | C40—C35—C36—C37 | 2.3 (14) |
C16—O4—C17—C18 | −19.4 (12) | C34—C35—C36—C37 | −179.1 (9) |
C16—O4—C17—C22 | 163.1 (7) | C35—C36—C37—C38 | −0.3 (17) |
C22—C17—C18—C19 | −2.5 (13) | C36—C37—C38—C39 | −1 (2) |
O4—C17—C18—C19 | −179.8 (8) | C37—C38—C39—C40 | 1 (2) |
C17—C18—C19—C20 | 0.9 (15) | C36—C35—C40—C39 | −2.7 (14) |
C18—C19—C20—C21 | 0.2 (15) | C34—C35—C40—C39 | 178.6 (9) |
C19—C20—C21—C22 | 0.3 (14) | C38—C39—C40—C35 | 1.1 (18) |
C20—C21—C22—C17 | −1.8 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···F7i | 0.93 | 2.32 | 3.233 (11) | 166 |
C3—H3···F11i | 0.93 | 2.47 | 3.217 (10) | 137 |
C20—H20···O6ii | 0.93 | 2.55 | 3.400 (11) | 152 |
C23—H23A···F12ii | 0.97 | 2.52 | 3.444 (11) | 159 |
C29—H29···F12ii | 0.93 | 2.53 | 3.401 (12) | 156 |
C41—H41B···F1ii | 0.96 | 2.51 | 3.039 (13) | 114 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z. |