Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026682/cv2254sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026682/cv2254Isup2.hkl |
CCDC reference: 654698
The ligand (R)-2,2'-bis[imidazolium-3-oxyethyl-1-(1-menaphthyl)]-1,1'-binaphthyl bis(hexafluorophosphate) was prepared according to the reported procedure (Scheele et al., 2006). A stirred acetonitrile solution (25 ml) of the corresponding diazolium salt (104.7 mg, 0.10 mmol) and anhydrous Hg(OAc)2 (29.5 mg, 0.10 mmol) was heated at 353 K for 12 h, The remaining acetonitrile was then removed in vacuo to give a white solid which was washed with methanol to give the crude product. White single crystals of the title compound were obtained by recrystallization from acetonitile and ethyl ether (yield: 80%) Anal. Calcd. for C118H105F24Hg2N15O4: C, 51.01; H, 3.81; N, 7.56 Found: C, 50.99; H, 3.76; N 7.49.
All H-atoms were geometrically positioned [C—H 0.93–0.97 Å] and refined as riding with Uiso(H) =1.2–1.5Ueq(C).
In the title compound, (I), the cation is a 15-membered macrocyclic metal complex of carbene-naphthoxy ligand adopting a trans-conformation. The short distance of 3.657 (4) Å between the centroids of C5—C10 and N3—C39—N4—C40—C41 rings shows a presence of intramolecular π···π interaction. The linear coordination geometry of the Hg ion is formed by two C atoms from the imidazole fragments [Hg—C 2.072 (6), 2.090 (6) Å, C—Hg—C 174.4 (2)°].
The crystal packing is stabilized by the weak C—H···F and C—H···N interactions (Table 1).
The related rhodium and iridium complexes of the carbene–naphthoxy ligands were applied to the catalytic asymmetric hydrosilylation of acetophenone with diphenylsilane; see: Chianese & Crabtree (2005); Scheele et al. (2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
Fig. 1. The cation structure of the title compound, shown with 30% probability displacement ellipsoids. Dashed lines indicate intramolecular hydrogen bonds and π-π stacking interactions. |
[Hg(C52H42N4O2)](PF6)2·3.5C2H3N | Z = 2 |
Mr = 1389.12 | F(000) = 1386 |
Triclinic, P1 | Dx = 1.565 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.266 (4) Å | Cell parameters from 923 reflections |
b = 14.908 (6) Å | θ = 2.8–22.6° |
c = 16.946 (6) Å | µ = 2.75 mm−1 |
α = 94.448 (6)° | T = 293 K |
β = 107.027 (6)° | Block, white |
γ = 92.066 (7)° | 0.20 × 0.14 × 0.12 mm |
V = 2948.4 (19) Å3 |
Bruker SMART CCD area-detector diffractometer | 11938 independent reflections |
Radiation source: fine-focus sealed tube | 8762 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
phi and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −15→11 |
Tmin = 0.634, Tmax = 0.782 | k = −18→16 |
17133 measured reflections | l = −20→21 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0627P)2] where P = (Fo2 + 2Fc2)/3 |
11938 reflections | (Δ/σ)max = 0.002 |
770 parameters | Δρmax = 0.97 e Å−3 |
21 restraints | Δρmin = −0.78 e Å−3 |
[Hg(C52H42N4O2)](PF6)2·3.5C2H3N | γ = 92.066 (7)° |
Mr = 1389.12 | V = 2948.4 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.266 (4) Å | Mo Kα radiation |
b = 14.908 (6) Å | µ = 2.75 mm−1 |
c = 16.946 (6) Å | T = 293 K |
α = 94.448 (6)° | 0.20 × 0.14 × 0.12 mm |
β = 107.027 (6)° |
Bruker SMART CCD area-detector diffractometer | 11938 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 8762 reflections with I > 2σ(I) |
Tmin = 0.634, Tmax = 0.782 | Rint = 0.031 |
17133 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 21 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.97 e Å−3 |
11938 reflections | Δρmin = −0.78 e Å−3 |
770 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Hg1 | 0.84498 (2) | 0.923454 (18) | 0.734041 (15) | 0.03985 (9) | |
N1 | 0.8148 (4) | 1.0221 (3) | 0.8924 (3) | 0.0415 (12) | |
N2 | 0.9675 (4) | 1.0740 (4) | 0.8693 (3) | 0.0410 (12) | |
N3 | 0.9075 (4) | 0.7732 (3) | 0.6265 (3) | 0.0403 (12) | |
N4 | 0.7265 (4) | 0.7915 (4) | 0.5801 (3) | 0.0436 (13) | |
O1 | 0.7722 (4) | 0.8275 (3) | 0.9203 (3) | 0.0497 (11) | |
O2 | 0.9873 (4) | 0.7644 (3) | 0.8017 (3) | 0.0461 (11) | |
C1 | 0.7833 (5) | 0.7046 (4) | 0.8293 (4) | 0.0392 (14) | |
C2 | 0.7187 (5) | 0.7712 (4) | 0.8499 (4) | 0.0407 (14) | |
C3 | 0.6032 (5) | 0.7774 (4) | 0.8034 (4) | 0.0465 (16) | |
H3 | 0.5597 | 0.8206 | 0.8201 | 0.056* | |
C4 | 0.5561 (5) | 0.7204 (5) | 0.7344 (4) | 0.0488 (16) | |
H4 | 0.4799 | 0.7244 | 0.7045 | 0.059* | |
C5 | 0.6209 (6) | 0.6547 (5) | 0.7070 (4) | 0.0462 (16) | |
C6 | 0.7356 (5) | 0.6464 (4) | 0.7555 (4) | 0.0400 (14) | |
C7 | 0.7973 (6) | 0.5790 (5) | 0.7277 (4) | 0.0530 (18) | |
H7 | 0.8714 | 0.5704 | 0.7593 | 0.064* | |
C8 | 0.7508 (7) | 0.5266 (5) | 0.6559 (5) | 0.067 (2) | |
H8 | 0.7941 | 0.4837 | 0.6386 | 0.081* | |
C9 | 0.6381 (7) | 0.5359 (6) | 0.6071 (5) | 0.069 (2) | |
H9 | 0.6076 | 0.4994 | 0.5579 | 0.082* | |
C10 | 0.5735 (6) | 0.5983 (5) | 0.6320 (5) | 0.0598 (19) | |
H10 | 0.4987 | 0.6040 | 0.6000 | 0.072* | |
C11 | 0.8988 (5) | 0.6914 (4) | 0.8872 (4) | 0.0402 (14) | |
C12 | 0.9974 (5) | 0.7190 (4) | 0.8714 (4) | 0.0406 (15) | |
C13 | 1.1056 (6) | 0.7054 (5) | 0.9259 (4) | 0.0514 (17) | |
H13 | 1.1716 | 0.7256 | 0.9146 | 0.062* | |
C14 | 1.1131 (6) | 0.6621 (5) | 0.9955 (4) | 0.058 (2) | |
H14 | 1.1846 | 0.6518 | 1.0305 | 0.070* | |
C15 | 1.0162 (7) | 0.6335 (5) | 1.0147 (4) | 0.0514 (18) | |
C16 | 0.9066 (6) | 0.6474 (5) | 0.9608 (4) | 0.0482 (16) | |
C17 | 0.8098 (7) | 0.6182 (5) | 0.9819 (5) | 0.065 (2) | |
H17 | 0.7374 | 0.6275 | 0.9475 | 0.078* | |
C18 | 0.8203 (10) | 0.5758 (6) | 1.0528 (6) | 0.084 (3) | |
H18 | 0.7554 | 0.5562 | 1.0659 | 0.101* | |
C19 | 0.9286 (10) | 0.5622 (6) | 1.1051 (5) | 0.082 (3) | |
H19 | 0.9354 | 0.5337 | 1.1530 | 0.099* | |
C20 | 1.0235 (8) | 0.5898 (5) | 1.0869 (5) | 0.070 (2) | |
H20 | 1.0948 | 0.5798 | 1.1225 | 0.084* | |
C21 | 0.7127 (6) | 0.9027 (4) | 0.9414 (4) | 0.0458 (16) | |
H21A | 0.7520 | 0.9273 | 0.9977 | 0.055* | |
H21B | 0.6363 | 0.8815 | 0.9397 | 0.055* | |
C22 | 0.7044 (5) | 0.9756 (4) | 0.8850 (4) | 0.0467 (16) | |
H22A | 0.6711 | 0.9498 | 0.8283 | 0.056* | |
H22B | 0.6534 | 1.0193 | 0.8970 | 0.056* | |
C23 | 0.8763 (5) | 1.0159 (4) | 0.8385 (4) | 0.0414 (15) | |
C24 | 0.8692 (6) | 1.0845 (5) | 0.9582 (4) | 0.0553 (18) | |
H24 | 0.8455 | 1.1004 | 1.0045 | 0.066* | |
C25 | 0.9630 (6) | 1.1177 (5) | 0.9423 (4) | 0.0522 (18) | |
H25 | 1.0154 | 1.1623 | 0.9749 | 0.063* | |
C26 | 1.0481 (5) | 1.1031 (5) | 0.8264 (4) | 0.0463 (16) | |
H26A | 1.0560 | 1.0537 | 0.7881 | 0.056* | |
H26B | 1.1223 | 1.1177 | 0.8667 | 0.056* | |
C27 | 1.0118 (5) | 1.1836 (4) | 0.7794 (4) | 0.0431 (15) | |
C28 | 0.9035 (6) | 1.2123 (5) | 0.7634 (5) | 0.061 (2) | |
H28 | 0.8509 | 1.1828 | 0.7840 | 0.074* | |
C29 | 0.8702 (7) | 1.2868 (6) | 0.7158 (6) | 0.073 (2) | |
H29 | 0.7958 | 1.3048 | 0.7049 | 0.088* | |
C30 | 0.9450 (9) | 1.3312 (6) | 0.6865 (5) | 0.075 (2) | |
H30 | 0.9222 | 1.3797 | 0.6556 | 0.089* | |
C31 | 1.0576 (7) | 1.3048 (5) | 0.7023 (4) | 0.0586 (19) | |
C32 | 1.0923 (6) | 1.2297 (5) | 0.7483 (4) | 0.0490 (17) | |
C33 | 1.2042 (6) | 1.2028 (6) | 0.7597 (5) | 0.062 (2) | |
H33 | 1.2287 | 1.1532 | 0.7887 | 0.075* | |
C34 | 1.2777 (8) | 1.2503 (7) | 0.7277 (6) | 0.081 (3) | |
H34 | 1.3513 | 1.2320 | 0.7348 | 0.097* | |
C35 | 1.2428 (10) | 1.3252 (7) | 0.6852 (6) | 0.086 (3) | |
H35 | 1.2939 | 1.3570 | 0.6649 | 0.103* | |
C36 | 1.1366 (9) | 1.3521 (6) | 0.6729 (5) | 0.073 (2) | |
H36 | 1.1150 | 1.4027 | 0.6446 | 0.088* | |
C37 | 1.0546 (5) | 0.7325 (5) | 0.7499 (4) | 0.0491 (17) | |
H37A | 1.0360 | 0.6688 | 0.7326 | 0.059* | |
H37B | 1.1353 | 0.7407 | 0.7800 | 0.059* | |
C38 | 1.0277 (5) | 0.7857 (5) | 0.6761 (4) | 0.0460 (16) | |
H38A | 1.0462 | 0.8491 | 0.6946 | 0.055* | |
H38B | 1.0753 | 0.7677 | 0.6416 | 0.055* | |
C39 | 0.8233 (5) | 0.8233 (4) | 0.6380 (3) | 0.0370 (14) | |
C40 | 0.8621 (6) | 0.7083 (5) | 0.5621 (4) | 0.0545 (18) | |
H40 | 0.9023 | 0.6647 | 0.5423 | 0.065* | |
C41 | 0.7516 (6) | 0.7183 (5) | 0.5329 (4) | 0.0536 (18) | |
H41 | 0.7000 | 0.6832 | 0.4892 | 0.064* | |
C42 | 0.6119 (5) | 0.8276 (4) | 0.5654 (4) | 0.0447 (15) | |
H42A | 0.5731 | 0.8007 | 0.6008 | 0.054* | |
H42B | 0.5672 | 0.8110 | 0.5083 | 0.054* | |
C43 | 0.6187 (5) | 0.9279 (5) | 0.5823 (4) | 0.0463 (16) | |
C44 | 0.5870 (6) | 0.9657 (6) | 0.6479 (4) | 0.059 (2) | |
H44 | 0.5616 | 0.9284 | 0.6812 | 0.070* | |
C45 | 0.5921 (7) | 1.0592 (7) | 0.6659 (6) | 0.077 (3) | |
H45 | 0.5695 | 1.0835 | 0.7105 | 0.093* | |
C46 | 0.6290 (7) | 1.1130 (6) | 0.6194 (7) | 0.079 (3) | |
H46 | 0.6345 | 1.1749 | 0.6334 | 0.095* | |
C47 | 0.6606 (6) | 1.0797 (6) | 0.5489 (6) | 0.067 (2) | |
C48 | 0.6555 (5) | 0.9848 (5) | 0.5302 (4) | 0.0503 (17) | |
C49 | 0.6852 (6) | 0.9507 (6) | 0.4588 (5) | 0.061 (2) | |
H49 | 0.6834 | 0.8887 | 0.4461 | 0.073* | |
C50 | 0.7165 (7) | 1.0083 (8) | 0.4086 (6) | 0.084 (3) | |
H50 | 0.7366 | 0.9851 | 0.3626 | 0.100* | |
C51 | 0.7181 (9) | 1.1014 (9) | 0.4262 (8) | 0.100 (4) | |
H51 | 0.7359 | 1.1397 | 0.3903 | 0.120* | |
C52 | 0.6943 (8) | 1.1366 (7) | 0.4947 (8) | 0.090 (3) | |
H52 | 0.6999 | 1.1988 | 0.5068 | 0.108* | |
P1 | 0.19960 (17) | 0.60006 (14) | 0.56869 (14) | 0.0595 (5) | |
P2 | 0.32712 (17) | 0.93227 (15) | 0.85090 (13) | 0.0612 (5) | |
F1 | 0.2784 (5) | 0.6251 (4) | 0.5131 (4) | 0.0935 (16) | |
F2 | 0.1375 (6) | 0.5222 (4) | 0.5022 (4) | 0.135 (3) | |
F3 | 0.1110 (4) | 0.6682 (4) | 0.5241 (3) | 0.0961 (17) | |
F4 | 0.2606 (5) | 0.6805 (4) | 0.6356 (3) | 0.0995 (17) | |
F5 | 0.2898 (5) | 0.5351 (4) | 0.6149 (5) | 0.129 (2) | |
F6 | 0.1198 (5) | 0.5779 (4) | 0.6244 (3) | 0.0908 (16) | |
F7 | 0.2254 (8) | 0.9111 (6) | 0.8835 (6) | 0.183 (4) | |
F8 | 0.4160 (12) | 0.9258 (8) | 0.9327 (7) | 0.275 (7) | |
F9 | 0.3290 (7) | 0.8325 (5) | 0.8279 (9) | 0.225 (6) | |
F10 | 0.2386 (6) | 0.9440 (7) | 0.7697 (4) | 0.165 (3) | |
F11 | 0.3235 (6) | 1.0328 (4) | 0.8804 (5) | 0.132 (2) | |
F12 | 0.4274 (6) | 0.9544 (6) | 0.8179 (7) | 0.185 (4) | |
N5 | 0.4918 (10) | 0.6825 (9) | 0.3671 (10) | 0.156 (5) | |
C53 | 0.4547 (12) | 0.6419 (10) | 0.3053 (12) | 0.129 (5) | |
C54 | 0.4075 (15) | 0.5882 (11) | 0.2256 (10) | 0.182 (7) | |
H54A | 0.4682 | 0.5606 | 0.2095 | 0.273* | |
H54B | 0.3697 | 0.6266 | 0.1843 | 0.273* | |
H54C | 0.3537 | 0.5422 | 0.2306 | 0.273* | |
N6 | −0.0360 (7) | 0.0136 (5) | 0.6310 (4) | 0.076 (2) | |
C55 | −0.0159 (7) | 0.0671 (6) | 0.5928 (5) | 0.0584 (19) | |
C56 | 0.0109 (8) | 0.1352 (5) | 0.5444 (5) | 0.071 (2) | |
H56A | 0.0822 | 0.1669 | 0.5747 | 0.106* | |
H56B | −0.0485 | 0.1768 | 0.5334 | 0.106* | |
H56C | 0.0169 | 0.1072 | 0.4930 | 0.106* | |
N7 | 0.3716 (18) | 0.7959 (13) | 0.1389 (12) | 0.183 (7) | |
C57 | 0.4303 (18) | 0.7870 (14) | 0.1027 (12) | 0.137 (7) | |
C58 | 0.5033 (18) | 0.7666 (15) | 0.0536 (12) | 0.211 (10) | |
H58A | 0.5739 | 0.7470 | 0.0879 | 0.316* | |
H58B | 0.5184 | 0.8194 | 0.0286 | 0.316* | |
H58C | 0.4671 | 0.7195 | 0.0110 | 0.316* | |
N8 | 0.3182 (17) | 0.5906 (14) | 0.8172 (12) | 0.116 (6) | 0.50 |
C59 | 0.3992 (19) | 0.5805 (17) | 0.8650 (15) | 0.127 (9) | 0.50 |
C60 | 0.501 (2) | 0.539 (2) | 0.9171 (19) | 0.198 (15) | 0.50 |
H60A | 0.5061 | 0.5507 | 0.9745 | 0.297* | 0.50 |
H60B | 0.5690 | 0.5636 | 0.9075 | 0.297* | 0.50 |
H60C | 0.4942 | 0.4747 | 0.9027 | 0.297* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.03965 (14) | 0.04213 (15) | 0.03645 (13) | 0.00516 (9) | 0.01044 (9) | −0.00233 (9) |
N1 | 0.047 (3) | 0.038 (3) | 0.040 (3) | 0.003 (2) | 0.016 (2) | −0.004 (2) |
N2 | 0.040 (3) | 0.043 (3) | 0.041 (3) | 0.003 (2) | 0.013 (2) | 0.003 (2) |
N3 | 0.045 (3) | 0.043 (3) | 0.036 (3) | 0.008 (2) | 0.015 (2) | 0.000 (2) |
N4 | 0.043 (3) | 0.044 (3) | 0.042 (3) | 0.001 (2) | 0.011 (2) | 0.004 (2) |
O1 | 0.048 (3) | 0.044 (3) | 0.052 (3) | 0.009 (2) | 0.010 (2) | −0.008 (2) |
O2 | 0.038 (2) | 0.057 (3) | 0.047 (2) | 0.013 (2) | 0.016 (2) | 0.008 (2) |
C1 | 0.039 (3) | 0.036 (3) | 0.043 (3) | 0.003 (3) | 0.012 (3) | 0.006 (3) |
C2 | 0.042 (4) | 0.037 (4) | 0.043 (3) | −0.002 (3) | 0.014 (3) | 0.000 (3) |
C3 | 0.037 (4) | 0.043 (4) | 0.062 (4) | 0.003 (3) | 0.019 (3) | 0.001 (3) |
C4 | 0.031 (3) | 0.051 (4) | 0.060 (4) | −0.002 (3) | 0.010 (3) | 0.002 (3) |
C5 | 0.043 (4) | 0.046 (4) | 0.047 (4) | −0.004 (3) | 0.011 (3) | 0.003 (3) |
C6 | 0.041 (4) | 0.036 (4) | 0.043 (3) | 0.000 (3) | 0.013 (3) | 0.003 (3) |
C7 | 0.047 (4) | 0.052 (4) | 0.056 (4) | 0.013 (3) | 0.011 (3) | −0.007 (3) |
C8 | 0.067 (5) | 0.060 (5) | 0.068 (5) | 0.021 (4) | 0.012 (4) | −0.012 (4) |
C9 | 0.074 (6) | 0.061 (5) | 0.060 (5) | 0.006 (4) | 0.006 (4) | −0.012 (4) |
C10 | 0.053 (4) | 0.059 (5) | 0.057 (4) | 0.002 (4) | 0.004 (3) | −0.006 (4) |
C11 | 0.040 (4) | 0.037 (4) | 0.041 (3) | 0.007 (3) | 0.008 (3) | 0.000 (3) |
C12 | 0.039 (4) | 0.041 (4) | 0.036 (3) | 0.010 (3) | 0.004 (3) | −0.002 (3) |
C13 | 0.039 (4) | 0.056 (4) | 0.053 (4) | 0.003 (3) | 0.006 (3) | −0.004 (3) |
C14 | 0.056 (5) | 0.053 (5) | 0.047 (4) | 0.013 (4) | −0.013 (3) | 0.007 (3) |
C15 | 0.071 (5) | 0.037 (4) | 0.038 (3) | 0.011 (3) | 0.005 (3) | −0.002 (3) |
C16 | 0.055 (4) | 0.042 (4) | 0.044 (4) | 0.006 (3) | 0.012 (3) | −0.001 (3) |
C17 | 0.066 (5) | 0.063 (5) | 0.069 (5) | 0.009 (4) | 0.023 (4) | 0.019 (4) |
C18 | 0.118 (8) | 0.069 (6) | 0.082 (6) | 0.007 (5) | 0.050 (6) | 0.024 (5) |
C19 | 0.129 (9) | 0.062 (6) | 0.053 (5) | 0.014 (6) | 0.017 (5) | 0.024 (4) |
C20 | 0.092 (7) | 0.052 (5) | 0.054 (5) | 0.008 (4) | 0.002 (4) | 0.011 (4) |
C21 | 0.052 (4) | 0.045 (4) | 0.045 (4) | 0.001 (3) | 0.024 (3) | −0.003 (3) |
C22 | 0.044 (4) | 0.045 (4) | 0.055 (4) | 0.003 (3) | 0.021 (3) | 0.000 (3) |
C23 | 0.042 (4) | 0.039 (4) | 0.042 (3) | 0.006 (3) | 0.010 (3) | 0.001 (3) |
C24 | 0.065 (5) | 0.054 (4) | 0.046 (4) | −0.003 (4) | 0.019 (3) | −0.014 (3) |
C25 | 0.056 (4) | 0.045 (4) | 0.049 (4) | −0.002 (3) | 0.010 (3) | −0.010 (3) |
C26 | 0.039 (4) | 0.051 (4) | 0.048 (4) | 0.001 (3) | 0.013 (3) | 0.007 (3) |
C27 | 0.042 (4) | 0.038 (4) | 0.042 (3) | 0.001 (3) | 0.003 (3) | −0.004 (3) |
C28 | 0.052 (4) | 0.054 (5) | 0.078 (5) | 0.012 (3) | 0.016 (4) | 0.011 (4) |
C29 | 0.060 (5) | 0.063 (6) | 0.087 (6) | 0.025 (4) | 0.006 (5) | 0.010 (5) |
C30 | 0.097 (7) | 0.058 (5) | 0.065 (5) | 0.024 (5) | 0.014 (5) | 0.015 (4) |
C31 | 0.083 (6) | 0.049 (4) | 0.043 (4) | 0.004 (4) | 0.018 (4) | 0.005 (3) |
C32 | 0.052 (4) | 0.047 (4) | 0.042 (4) | 0.004 (3) | 0.005 (3) | 0.000 (3) |
C33 | 0.058 (5) | 0.071 (5) | 0.060 (5) | −0.002 (4) | 0.020 (4) | 0.013 (4) |
C34 | 0.065 (6) | 0.093 (7) | 0.091 (6) | −0.004 (5) | 0.028 (5) | 0.027 (6) |
C35 | 0.108 (8) | 0.081 (7) | 0.075 (6) | −0.031 (6) | 0.041 (6) | 0.010 (5) |
C36 | 0.099 (7) | 0.059 (5) | 0.063 (5) | −0.004 (5) | 0.022 (5) | 0.014 (4) |
C37 | 0.037 (4) | 0.062 (5) | 0.049 (4) | 0.009 (3) | 0.016 (3) | −0.004 (3) |
C38 | 0.038 (4) | 0.053 (4) | 0.052 (4) | 0.008 (3) | 0.021 (3) | 0.002 (3) |
C39 | 0.039 (3) | 0.039 (4) | 0.034 (3) | 0.000 (3) | 0.012 (3) | 0.004 (3) |
C40 | 0.062 (5) | 0.053 (4) | 0.050 (4) | 0.008 (4) | 0.021 (4) | −0.006 (3) |
C41 | 0.066 (5) | 0.047 (4) | 0.042 (4) | −0.002 (3) | 0.012 (3) | −0.011 (3) |
C42 | 0.036 (3) | 0.049 (4) | 0.046 (4) | 0.003 (3) | 0.006 (3) | 0.012 (3) |
C43 | 0.035 (3) | 0.050 (4) | 0.044 (4) | 0.005 (3) | −0.002 (3) | 0.002 (3) |
C44 | 0.052 (4) | 0.073 (6) | 0.046 (4) | 0.018 (4) | 0.005 (3) | 0.008 (4) |
C45 | 0.062 (5) | 0.090 (7) | 0.068 (6) | 0.021 (5) | 0.004 (4) | −0.018 (5) |
C46 | 0.056 (5) | 0.053 (5) | 0.104 (7) | 0.016 (4) | −0.010 (5) | −0.018 (5) |
C47 | 0.038 (4) | 0.056 (5) | 0.091 (6) | 0.001 (3) | −0.010 (4) | 0.012 (5) |
C48 | 0.031 (3) | 0.053 (4) | 0.057 (4) | −0.001 (3) | −0.003 (3) | 0.012 (3) |
C49 | 0.049 (4) | 0.073 (5) | 0.060 (5) | 0.006 (4) | 0.009 (4) | 0.022 (4) |
C50 | 0.066 (6) | 0.102 (8) | 0.089 (7) | 0.010 (5) | 0.027 (5) | 0.035 (6) |
C51 | 0.073 (7) | 0.100 (9) | 0.128 (10) | −0.010 (6) | 0.023 (7) | 0.052 (8) |
C52 | 0.054 (5) | 0.061 (6) | 0.137 (10) | −0.006 (4) | −0.007 (6) | 0.034 (6) |
P1 | 0.0561 (12) | 0.0521 (12) | 0.0762 (13) | 0.0048 (9) | 0.0300 (10) | 0.0009 (10) |
P2 | 0.0511 (12) | 0.0636 (14) | 0.0654 (12) | 0.0107 (10) | 0.0131 (10) | −0.0023 (10) |
F1 | 0.094 (4) | 0.086 (4) | 0.126 (4) | 0.011 (3) | 0.070 (3) | 0.016 (3) |
F2 | 0.135 (5) | 0.115 (5) | 0.160 (6) | −0.048 (4) | 0.080 (5) | −0.074 (5) |
F3 | 0.081 (4) | 0.128 (5) | 0.087 (3) | 0.045 (3) | 0.029 (3) | 0.023 (3) |
F4 | 0.103 (4) | 0.087 (4) | 0.092 (4) | −0.021 (3) | 0.013 (3) | −0.014 (3) |
F5 | 0.114 (5) | 0.111 (5) | 0.196 (7) | 0.061 (4) | 0.076 (5) | 0.082 (5) |
F6 | 0.103 (4) | 0.087 (4) | 0.107 (4) | 0.001 (3) | 0.069 (3) | 0.008 (3) |
F7 | 0.224 (9) | 0.172 (8) | 0.223 (9) | −0.023 (6) | 0.179 (8) | 0.016 (7) |
F8 | 0.303 (14) | 0.206 (11) | 0.186 (10) | 0.014 (10) | −0.140 (10) | 0.059 (8) |
F9 | 0.128 (6) | 0.073 (5) | 0.454 (17) | −0.001 (4) | 0.080 (8) | −0.077 (7) |
F10 | 0.130 (6) | 0.259 (11) | 0.078 (4) | −0.013 (6) | −0.009 (4) | 0.013 (5) |
F11 | 0.114 (5) | 0.092 (5) | 0.180 (7) | 0.020 (4) | 0.037 (5) | −0.027 (5) |
F12 | 0.088 (5) | 0.175 (8) | 0.314 (12) | −0.024 (5) | 0.116 (7) | −0.058 (8) |
N5 | 0.100 (8) | 0.114 (10) | 0.226 (16) | 0.006 (7) | 0.017 (9) | −0.032 (10) |
C53 | 0.093 (10) | 0.097 (11) | 0.197 (17) | −0.009 (7) | 0.049 (11) | −0.004 (10) |
C54 | 0.212 (18) | 0.165 (16) | 0.160 (15) | −0.069 (13) | 0.060 (13) | −0.012 (13) |
N6 | 0.097 (6) | 0.062 (5) | 0.068 (4) | −0.013 (4) | 0.025 (4) | 0.008 (4) |
C55 | 0.060 (5) | 0.059 (5) | 0.052 (4) | −0.004 (4) | 0.016 (4) | −0.007 (4) |
C56 | 0.095 (6) | 0.058 (5) | 0.064 (5) | −0.004 (4) | 0.029 (5) | 0.014 (4) |
N7 | 0.20 (2) | 0.141 (13) | 0.184 (17) | 0.008 (13) | 0.030 (13) | −0.007 (12) |
C57 | 0.149 (19) | 0.131 (15) | 0.113 (14) | −0.009 (13) | 0.008 (11) | 0.038 (12) |
C58 | 0.21 (2) | 0.26 (3) | 0.147 (16) | −0.010 (18) | 0.014 (15) | 0.083 (17) |
N8 | 0.114 (9) | 0.120 (10) | 0.112 (9) | 0.023 (8) | 0.023 (8) | 0.022 (8) |
C59 | 0.127 (12) | 0.134 (12) | 0.128 (12) | −0.015 (9) | 0.050 (9) | 0.013 (9) |
C60 | 0.201 (17) | 0.205 (18) | 0.195 (17) | −0.002 (10) | 0.071 (10) | 0.025 (10) |
Hg1—C39 | 2.072 (6) | C31—C36 | 1.405 (12) |
Hg1—C23 | 2.090 (6) | C31—C32 | 1.420 (10) |
N1—C23 | 1.345 (8) | C32—C33 | 1.407 (10) |
N1—C24 | 1.383 (8) | C33—C34 | 1.381 (11) |
N1—C22 | 1.466 (8) | C33—H33 | 0.9300 |
N2—C23 | 1.338 (8) | C34—C35 | 1.388 (13) |
N2—C25 | 1.369 (8) | C34—H34 | 0.9300 |
N2—C26 | 1.461 (8) | C35—C36 | 1.339 (13) |
N3—C39 | 1.346 (8) | C35—H35 | 0.9300 |
N3—C40 | 1.372 (8) | C36—H36 | 0.9300 |
N3—C38 | 1.465 (8) | C37—C38 | 1.494 (9) |
N4—C39 | 1.342 (7) | C37—H37A | 0.9700 |
N4—C41 | 1.400 (8) | C37—H37B | 0.9700 |
N4—C42 | 1.482 (8) | C38—H38A | 0.9700 |
O1—C2 | 1.380 (7) | C38—H38B | 0.9700 |
O1—C21 | 1.437 (7) | C40—C41 | 1.318 (10) |
O2—C12 | 1.382 (7) | C40—H40 | 0.9300 |
O2—C37 | 1.437 (7) | C41—H41 | 0.9300 |
C1—C2 | 1.379 (9) | C42—C43 | 1.494 (9) |
C1—C6 | 1.423 (8) | C42—H42A | 0.9700 |
C1—C11 | 1.498 (8) | C42—H42B | 0.9700 |
C2—C3 | 1.416 (9) | C43—C44 | 1.369 (10) |
C3—C4 | 1.355 (9) | C43—C48 | 1.424 (10) |
C3—H3 | 0.9300 | C44—C45 | 1.399 (12) |
C4—C5 | 1.417 (9) | C44—H44 | 0.9300 |
C4—H4 | 0.9300 | C45—C46 | 1.323 (13) |
C5—C6 | 1.421 (9) | C45—H45 | 0.9300 |
C5—C10 | 1.424 (9) | C46—C47 | 1.421 (13) |
C6—C7 | 1.413 (9) | C46—H46 | 0.9300 |
C7—C8 | 1.352 (10) | C47—C48 | 1.420 (10) |
C7—H7 | 0.9300 | C47—C52 | 1.433 (14) |
C8—C9 | 1.405 (10) | C48—C49 | 1.425 (10) |
C8—H8 | 0.9300 | C49—C50 | 1.375 (12) |
C9—C10 | 1.363 (10) | C49—H49 | 0.9300 |
C9—H9 | 0.9300 | C50—C51 | 1.396 (15) |
C10—H10 | 0.9300 | C50—H50 | 0.9300 |
C11—C12 | 1.369 (9) | C51—C52 | 1.350 (15) |
C11—C16 | 1.433 (9) | C51—H51 | 0.9300 |
C12—C13 | 1.410 (9) | C52—H52 | 0.9300 |
C13—C14 | 1.369 (10) | P1—F2 | 1.558 (6) |
C13—H13 | 0.9300 | P1—F5 | 1.570 (6) |
C14—C15 | 1.383 (11) | P1—F3 | 1.582 (5) |
C14—H14 | 0.9300 | P1—F4 | 1.584 (5) |
C15—C20 | 1.413 (10) | P1—F1 | 1.589 (5) |
C15—C16 | 1.419 (9) | P1—F6 | 1.589 (5) |
C16—C17 | 1.402 (10) | P2—F8 | 1.504 (8) |
C17—C18 | 1.376 (11) | P2—F10 | 1.510 (7) |
C17—H17 | 0.9300 | P2—F9 | 1.510 (7) |
C18—C19 | 1.396 (13) | P2—F12 | 1.529 (7) |
C18—H18 | 0.9300 | P2—F7 | 1.538 (7) |
C19—C20 | 1.345 (13) | P2—F11 | 1.549 (6) |
C19—H19 | 0.9300 | N5—C53 | 1.127 (18) |
C20—H20 | 0.9300 | C53—C54 | 1.46 (2) |
C21—C22 | 1.489 (9) | C54—H54A | 0.9600 |
C21—H21A | 0.9700 | C54—H54B | 0.9600 |
C21—H21B | 0.9700 | C54—H54C | 0.9600 |
C22—H22A | 0.9700 | N6—C55 | 1.129 (10) |
C22—H22B | 0.9700 | C55—C56 | 1.439 (11) |
C24—C25 | 1.342 (10) | C56—H56A | 0.9600 |
C24—H24 | 0.9300 | C56—H56B | 0.9600 |
C25—H25 | 0.9300 | C56—H56C | 0.9600 |
C26—C27 | 1.501 (9) | N7—C57 | 1.08 (2) |
C26—H26A | 0.9700 | C57—C58 | 1.42 (2) |
C26—H26B | 0.9700 | C58—H58A | 0.9600 |
C27—C28 | 1.367 (9) | C58—H58B | 0.9600 |
C27—C32 | 1.427 (10) | C58—H58C | 0.9600 |
C28—C29 | 1.425 (11) | N8—C59 | 1.107 (9) |
C28—H28 | 0.9300 | C59—C60 | 1.493 (9) |
C29—C30 | 1.342 (12) | C60—H60A | 0.9600 |
C29—H29 | 0.9300 | C60—H60B | 0.9600 |
C30—C31 | 1.404 (12) | C60—H60C | 0.9600 |
C30—H30 | 0.9300 | ||
C39—Hg1—C23 | 174.4 (2) | C33—C34—H34 | 119.6 |
C23—N1—C24 | 109.4 (5) | C35—C34—H34 | 119.6 |
C23—N1—C22 | 128.0 (5) | C36—C35—C34 | 120.8 (9) |
C24—N1—C22 | 122.6 (5) | C36—C35—H35 | 119.6 |
C23—N2—C25 | 109.7 (6) | C34—C35—H35 | 119.6 |
C23—N2—C26 | 126.8 (5) | C35—C36—C31 | 120.7 (9) |
C25—N2—C26 | 122.3 (6) | C35—C36—H36 | 119.7 |
C39—N3—C40 | 109.0 (5) | C31—C36—H36 | 119.7 |
C39—N3—C38 | 125.2 (5) | O2—C37—C38 | 107.5 (5) |
C40—N3—C38 | 125.8 (5) | O2—C37—H37A | 110.2 |
C39—N4—C41 | 108.4 (6) | C38—C37—H37A | 110.2 |
C39—N4—C42 | 127.0 (5) | O2—C37—H37B | 110.2 |
C41—N4—C42 | 124.6 (5) | C38—C37—H37B | 110.2 |
C2—O1—C21 | 118.4 (5) | H37A—C37—H37B | 108.5 |
C12—O2—C37 | 115.3 (5) | N3—C38—C37 | 112.7 (5) |
C2—C1—C6 | 118.9 (6) | N3—C38—H38A | 109.1 |
C2—C1—C11 | 119.5 (5) | C37—C38—H38A | 109.1 |
C6—C1—C11 | 121.4 (5) | N3—C38—H38B | 109.1 |
C1—C2—O1 | 115.8 (5) | C37—C38—H38B | 109.1 |
C1—C2—C3 | 121.2 (6) | H38A—C38—H38B | 107.8 |
O1—C2—C3 | 122.9 (6) | N4—C39—N3 | 107.1 (5) |
C4—C3—C2 | 120.0 (6) | N4—C39—Hg1 | 128.6 (5) |
C4—C3—H3 | 120.0 | N3—C39—Hg1 | 124.1 (4) |
C2—C3—H3 | 120.0 | C41—C40—N3 | 108.3 (6) |
C3—C4—C5 | 121.1 (6) | C41—C40—H40 | 125.8 |
C3—C4—H4 | 119.4 | N3—C40—H40 | 125.8 |
C5—C4—H4 | 119.4 | C40—C41—N4 | 107.2 (6) |
C4—C5—C6 | 118.8 (6) | C40—C41—H41 | 126.4 |
C4—C5—C10 | 121.2 (6) | N4—C41—H41 | 126.4 |
C6—C5—C10 | 120.0 (6) | N4—C42—C43 | 112.0 (5) |
C7—C6—C5 | 117.5 (6) | N4—C42—H42A | 109.2 |
C7—C6—C1 | 122.8 (6) | C43—C42—H42A | 109.2 |
C5—C6—C1 | 119.7 (6) | N4—C42—H42B | 109.2 |
C8—C7—C6 | 121.4 (6) | C43—C42—H42B | 109.2 |
C8—C7—H7 | 119.3 | H42A—C42—H42B | 107.9 |
C6—C7—H7 | 119.3 | C44—C43—C48 | 119.4 (7) |
C7—C8—C9 | 121.1 (7) | C44—C43—C42 | 119.7 (7) |
C7—C8—H8 | 119.4 | C48—C43—C42 | 120.9 (6) |
C9—C8—H8 | 119.4 | C43—C44—C45 | 121.6 (8) |
C10—C9—C8 | 120.1 (7) | C43—C44—H44 | 119.2 |
C10—C9—H9 | 120.0 | C45—C44—H44 | 119.2 |
C8—C9—H9 | 120.0 | C46—C45—C44 | 119.8 (9) |
C9—C10—C5 | 119.9 (7) | C46—C45—H45 | 120.1 |
C9—C10—H10 | 120.1 | C44—C45—H45 | 120.1 |
C5—C10—H10 | 120.1 | C45—C46—C47 | 122.4 (9) |
C12—C11—C16 | 118.9 (6) | C45—C46—H46 | 118.8 |
C12—C11—C1 | 122.0 (6) | C47—C46—H46 | 118.8 |
C16—C11—C1 | 119.2 (6) | C48—C47—C46 | 118.0 (8) |
C11—C12—O2 | 117.7 (5) | C48—C47—C52 | 118.5 (9) |
C11—C12—C13 | 121.5 (6) | C46—C47—C52 | 123.5 (9) |
O2—C12—C13 | 120.8 (6) | C47—C48—C43 | 118.8 (7) |
C14—C13—C12 | 119.6 (7) | C47—C48—C49 | 118.5 (7) |
C14—C13—H13 | 120.2 | C43—C48—C49 | 122.7 (7) |
C12—C13—H13 | 120.2 | C50—C49—C48 | 120.7 (9) |
C13—C14—C15 | 121.2 (6) | C50—C49—H49 | 119.6 |
C13—C14—H14 | 119.4 | C48—C49—H49 | 119.6 |
C15—C14—H14 | 119.4 | C49—C50—C51 | 120.4 (10) |
C14—C15—C20 | 121.4 (7) | C49—C50—H50 | 119.8 |
C14—C15—C16 | 119.8 (6) | C51—C50—H50 | 119.8 |
C20—C15—C16 | 118.9 (8) | C52—C51—C50 | 120.8 (10) |
C17—C16—C15 | 118.6 (7) | C52—C51—H51 | 119.6 |
C17—C16—C11 | 122.4 (6) | C50—C51—H51 | 119.6 |
C15—C16—C11 | 119.1 (6) | C51—C52—C47 | 121.1 (10) |
C18—C17—C16 | 120.9 (8) | C51—C52—H52 | 119.5 |
C18—C17—H17 | 119.5 | C47—C52—H52 | 119.5 |
C16—C17—H17 | 119.5 | F2—P1—F5 | 91.3 (4) |
C17—C18—C19 | 119.8 (9) | F2—P1—F3 | 90.5 (4) |
C17—C18—H18 | 120.1 | F5—P1—F3 | 178.1 (4) |
C19—C18—H18 | 120.1 | F2—P1—F4 | 178.8 (4) |
C20—C19—C18 | 120.9 (8) | F5—P1—F4 | 89.9 (4) |
C20—C19—H19 | 119.5 | F3—P1—F4 | 88.3 (3) |
C18—C19—H19 | 119.5 | F2—P1—F1 | 90.0 (3) |
C19—C20—C15 | 120.9 (8) | F5—P1—F1 | 90.5 (3) |
C19—C20—H20 | 119.5 | F3—P1—F1 | 89.3 (3) |
C15—C20—H20 | 119.5 | F4—P1—F1 | 90.2 (3) |
O1—C21—C22 | 113.2 (5) | F2—P1—F6 | 90.9 (3) |
O1—C21—H21A | 108.9 | F5—P1—F6 | 90.8 (3) |
C22—C21—H21A | 108.9 | F3—P1—F6 | 89.4 (3) |
O1—C21—H21B | 108.9 | F4—P1—F6 | 88.8 (3) |
C22—C21—H21B | 108.9 | F1—P1—F6 | 178.4 (3) |
H21A—C21—H21B | 107.8 | F8—P2—F10 | 177.0 (6) |
N1—C22—C21 | 113.5 (6) | F8—P2—F9 | 91.0 (7) |
N1—C22—H22A | 108.9 | F10—P2—F9 | 91.9 (6) |
C21—C22—H22A | 108.9 | F8—P2—F12 | 85.9 (7) |
N1—C22—H22B | 108.9 | F10—P2—F12 | 93.5 (5) |
C21—C22—H22B | 108.9 | F9—P2—F12 | 92.3 (5) |
H22A—C22—H22B | 107.7 | F8—P2—F7 | 94.6 (8) |
N2—C23—N1 | 106.7 (5) | F10—P2—F7 | 85.9 (5) |
N2—C23—Hg1 | 126.6 (5) | F9—P2—F7 | 88.3 (5) |
N1—C23—Hg1 | 126.4 (5) | F12—P2—F7 | 179.2 (6) |
C25—C24—N1 | 106.6 (6) | F8—P2—F11 | 86.5 (6) |
C25—C24—H24 | 126.7 | F10—P2—F11 | 90.6 (5) |
N1—C24—H24 | 126.7 | F9—P2—F11 | 175.8 (6) |
C24—C25—N2 | 107.6 (6) | F12—P2—F11 | 90.9 (4) |
C24—C25—H25 | 126.2 | F7—P2—F11 | 88.5 (4) |
N2—C25—H25 | 126.2 | N5—C53—C54 | 179 (2) |
N2—C26—C27 | 113.0 (5) | C53—C54—H54A | 109.5 |
N2—C26—H26A | 109.0 | C53—C54—H54B | 109.5 |
C27—C26—H26A | 109.0 | H54A—C54—H54B | 109.5 |
N2—C26—H26B | 109.0 | C53—C54—H54C | 109.5 |
C27—C26—H26B | 109.0 | H54A—C54—H54C | 109.5 |
H26A—C26—H26B | 107.8 | H54B—C54—H54C | 109.5 |
C28—C27—C32 | 119.3 (7) | N6—C55—C56 | 179.5 (10) |
C28—C27—C26 | 122.1 (6) | C55—C56—H56A | 109.5 |
C32—C27—C26 | 118.6 (6) | C55—C56—H56B | 109.5 |
C27—C28—C29 | 120.8 (8) | H56A—C56—H56B | 109.5 |
C27—C28—H28 | 119.6 | C55—C56—H56C | 109.5 |
C29—C28—H28 | 119.6 | H56A—C56—H56C | 109.5 |
C30—C29—C28 | 120.6 (8) | H56B—C56—H56C | 109.5 |
C30—C29—H29 | 119.7 | N7—C57—C58 | 174 (3) |
C28—C29—H29 | 119.7 | C57—C58—H58A | 109.5 |
C29—C30—C31 | 120.4 (8) | C57—C58—H58B | 109.5 |
C29—C30—H30 | 119.8 | H58A—C58—H58B | 109.5 |
C31—C30—H30 | 119.8 | C57—C58—H58C | 109.5 |
C30—C31—C36 | 120.5 (8) | H58A—C58—H58C | 109.5 |
C30—C31—C32 | 120.0 (7) | H58B—C58—H58C | 109.5 |
C36—C31—C32 | 119.5 (8) | N8—C59—C60 | 163 (3) |
C33—C32—C31 | 118.3 (7) | C59—C60—H60A | 109.5 |
C33—C32—C27 | 122.8 (7) | C59—C60—H60B | 109.5 |
C31—C32—C27 | 118.8 (7) | H60A—C60—H60B | 109.5 |
C34—C33—C32 | 119.8 (8) | C59—C60—H60C | 109.5 |
C34—C33—H33 | 120.1 | H60A—C60—H60C | 109.5 |
C32—C33—H33 | 120.1 | H60B—C60—H60C | 109.5 |
C33—C34—C35 | 120.7 (9) | ||
C6—C1—C2—O1 | −177.3 (5) | N1—C24—C25—N2 | −2.0 (8) |
C11—C1—C2—O1 | 6.3 (9) | C23—N2—C25—C24 | 1.7 (8) |
C6—C1—C2—C3 | 5.8 (9) | C26—N2—C25—C24 | 169.9 (6) |
C11—C1—C2—C3 | −170.6 (6) | C23—N2—C26—C27 | 88.2 (8) |
C21—O1—C2—C1 | 175.1 (6) | C25—N2—C26—C27 | −77.9 (7) |
C21—O1—C2—C3 | −8.0 (9) | N2—C26—C27—C28 | −14.1 (9) |
C1—C2—C3—C4 | −3.8 (10) | N2—C26—C27—C32 | 167.9 (5) |
O1—C2—C3—C4 | 179.5 (6) | C32—C27—C28—C29 | 0.6 (11) |
C2—C3—C4—C5 | −0.8 (10) | C26—C27—C28—C29 | −177.5 (7) |
C3—C4—C5—C6 | 3.0 (10) | C27—C28—C29—C30 | −1.0 (13) |
C3—C4—C5—C10 | −176.3 (7) | C28—C29—C30—C31 | 0.1 (13) |
C4—C5—C6—C7 | 178.6 (6) | C29—C30—C31—C36 | −179.0 (8) |
C10—C5—C6—C7 | −2.1 (10) | C29—C30—C31—C32 | 1.1 (12) |
C4—C5—C6—C1 | −0.9 (9) | C30—C31—C32—C33 | 177.2 (7) |
C10—C5—C6—C1 | 178.4 (6) | C36—C31—C32—C33 | −2.7 (10) |
C2—C1—C6—C7 | 177.1 (7) | C30—C31—C32—C27 | −1.5 (10) |
C11—C1—C6—C7 | −6.5 (10) | C36—C31—C32—C27 | 178.6 (7) |
C2—C1—C6—C5 | −3.4 (9) | C28—C27—C32—C33 | −178.0 (7) |
C11—C1—C6—C5 | 172.9 (6) | C26—C27—C32—C33 | 0.2 (10) |
C5—C6—C7—C8 | 2.6 (11) | C28—C27—C32—C31 | 0.6 (10) |
C1—C6—C7—C8 | −177.9 (7) | C26—C27—C32—C31 | 178.8 (6) |
C6—C7—C8—C9 | −1.5 (13) | C31—C32—C33—C34 | 1.2 (11) |
C7—C8—C9—C10 | −0.2 (14) | C27—C32—C33—C34 | 179.8 (7) |
C8—C9—C10—C5 | 0.7 (13) | C32—C33—C34—C35 | 0.8 (13) |
C4—C5—C10—C9 | 179.8 (8) | C33—C34—C35—C36 | −1.2 (15) |
C6—C5—C10—C9 | 0.5 (11) | C34—C35—C36—C31 | −0.4 (14) |
C2—C1—C11—C12 | −104.9 (7) | C30—C31—C36—C35 | −177.5 (8) |
C6—C1—C11—C12 | 78.8 (8) | C32—C31—C36—C35 | 2.4 (12) |
C2—C1—C11—C16 | 76.1 (8) | C12—O2—C37—C38 | 176.9 (5) |
C6—C1—C11—C16 | −100.2 (7) | C39—N3—C38—C37 | 89.3 (7) |
C16—C11—C12—O2 | −177.6 (5) | C40—N3—C38—C37 | −89.5 (7) |
C1—C11—C12—O2 | 3.4 (9) | O2—C37—C38—N3 | −61.9 (7) |
C16—C11—C12—C13 | −0.2 (9) | C41—N4—C39—N3 | 1.6 (7) |
C1—C11—C12—C13 | −179.3 (6) | C42—N4—C39—N3 | −177.0 (6) |
C37—O2—C12—C11 | −131.8 (6) | C41—N4—C39—Hg1 | −174.4 (5) |
C37—O2—C12—C13 | 50.9 (8) | C42—N4—C39—Hg1 | 7.0 (9) |
C11—C12—C13—C14 | 1.2 (10) | C40—N3—C39—N4 | −1.5 (7) |
O2—C12—C13—C14 | 178.4 (6) | C38—N3—C39—N4 | 179.5 (5) |
C12—C13—C14—C15 | −1.7 (11) | C40—N3—C39—Hg1 | 174.7 (5) |
C13—C14—C15—C20 | −179.3 (7) | C38—N3—C39—Hg1 | −4.3 (8) |
C13—C14—C15—C16 | 1.3 (11) | C23—Hg1—C39—N4 | 132 (2) |
C14—C15—C16—C17 | −179.7 (7) | C23—Hg1—C39—N3 | −43 (3) |
C20—C15—C16—C17 | 0.8 (10) | C39—N3—C40—C41 | 0.9 (8) |
C14—C15—C16—C11 | −0.3 (10) | C38—N3—C40—C41 | 179.9 (6) |
C20—C15—C16—C11 | −179.7 (6) | N3—C40—C41—N4 | 0.1 (8) |
C12—C11—C16—C17 | 179.2 (6) | C39—N4—C41—C40 | −1.0 (8) |
C1—C11—C16—C17 | −1.7 (10) | C42—N4—C41—C40 | 177.6 (6) |
C12—C11—C16—C15 | −0.2 (9) | C39—N4—C42—C43 | 34.2 (9) |
C1—C11—C16—C15 | 178.8 (6) | C41—N4—C42—C43 | −144.1 (6) |
C15—C16—C17—C18 | −0.9 (11) | N4—C42—C43—C44 | −112.5 (7) |
C11—C16—C17—C18 | 179.7 (7) | N4—C42—C43—C48 | 68.8 (7) |
C16—C17—C18—C19 | 0.6 (13) | C48—C43—C44—C45 | −1.3 (10) |
C17—C18—C19—C20 | −0.2 (14) | C42—C43—C44—C45 | 180.0 (6) |
C18—C19—C20—C15 | 0.2 (13) | C43—C44—C45—C46 | −0.5 (12) |
C14—C15—C20—C19 | 180.0 (8) | C44—C45—C46—C47 | 2.3 (13) |
C16—C15—C20—C19 | −0.6 (11) | C45—C46—C47—C48 | −2.2 (12) |
C2—O1—C21—C22 | −71.7 (7) | C45—C46—C47—C52 | 176.1 (8) |
C23—N1—C22—C21 | 107.3 (7) | C46—C47—C48—C43 | 0.3 (9) |
C24—N1—C22—C21 | −75.7 (8) | C52—C47—C48—C43 | −178.1 (6) |
O1—C21—C22—N1 | −67.6 (7) | C46—C47—C48—C49 | 179.0 (6) |
C25—N2—C23—N1 | −0.7 (7) | C52—C47—C48—C49 | 0.6 (10) |
C26—N2—C23—N1 | −168.2 (6) | C44—C43—C48—C47 | 1.3 (9) |
C25—N2—C23—Hg1 | −174.5 (5) | C42—C43—C48—C47 | −180.0 (6) |
C26—N2—C23—Hg1 | 18.0 (9) | C44—C43—C48—C49 | −177.3 (6) |
C24—N1—C23—N2 | −0.5 (7) | C42—C43—C48—C49 | 1.5 (9) |
C22—N1—C23—N2 | 176.8 (6) | C47—C48—C49—C50 | −0.9 (10) |
C24—N1—C23—Hg1 | 173.3 (5) | C43—C48—C49—C50 | 177.7 (7) |
C22—N1—C23—Hg1 | −9.4 (9) | C48—C49—C50—C51 | −0.9 (13) |
C39—Hg1—C23—N2 | 86 (3) | C49—C50—C51—C52 | 3.1 (15) |
C39—Hg1—C23—N1 | −87 (3) | C50—C51—C52—C47 | −3.4 (15) |
C23—N1—C24—C25 | 1.6 (8) | C48—C47—C52—C51 | 1.6 (13) |
C22—N1—C24—C25 | −176.0 (6) | C46—C47—C52—C51 | −176.7 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21A···F11i | 0.97 | 2.54 | 3.257 (10) | 131 |
C24—H24···F7i | 0.93 | 2.32 | 3.217 (12) | 161 |
C38—H38B···F3ii | 0.97 | 2.54 | 3.423 (9) | 151 |
C58—H58B···F8iii | 0.96 | 2.47 | 3.26 (2) | 140 |
C26—H26A···N6iv | 0.97 | 2.58 | 3.320 (9) | 133 |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Hg(C52H42N4O2)](PF6)2·3.5C2H3N |
Mr | 1389.12 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 12.266 (4), 14.908 (6), 16.946 (6) |
α, β, γ (°) | 94.448 (6), 107.027 (6), 92.066 (7) |
V (Å3) | 2948.4 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.75 |
Crystal size (mm) | 0.20 × 0.14 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.634, 0.782 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17133, 11938, 8762 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.127, 1.04 |
No. of reflections | 11938 |
No. of parameters | 770 |
No. of restraints | 21 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.97, −0.78 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL and local programs.
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21A···F11i | 0.97 | 2.54 | 3.257 (10) | 131 |
C24—H24···F7i | 0.93 | 2.32 | 3.217 (12) | 161 |
C38—H38B···F3ii | 0.97 | 2.54 | 3.423 (9) | 151 |
C58—H58B···F8iii | 0.96 | 2.47 | 3.26 (2) | 140 |
C26—H26A···N6iv | 0.97 | 2.58 | 3.320 (9) | 133 |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) x, y, z−1; (iv) x+1, y+1, z. |
In the title compound, (I), the cation is a 15-membered macrocyclic metal complex of carbene-naphthoxy ligand adopting a trans-conformation. The short distance of 3.657 (4) Å between the centroids of C5—C10 and N3—C39—N4—C40—C41 rings shows a presence of intramolecular π···π interaction. The linear coordination geometry of the Hg ion is formed by two C atoms from the imidazole fragments [Hg—C 2.072 (6), 2.090 (6) Å, C—Hg—C 174.4 (2)°].
The crystal packing is stabilized by the weak C—H···F and C—H···N interactions (Table 1).