{(R)-1,1′-Bis(1-naphthyl­meth­yl)-3,3′-[1,1′-binaphthyl-2,2′-diyldi(oxyethyl­ene)]di-1H-imidazol-2-yl}mercury(II) bis­(hexa­fluorido­phosphate) acetonitrile 3.5-solvate

Lin, J.; Dong, G.-Y.

doi:10.1107/S1600536807026682

Buy article online - an online subscription or single-article purchase is required to access this article.

{(R)-1,1′-Bis(1-naphthylmethyl)-3,3′-[1,1′-binaphthyl-2,2′-diyldi(oxyethylene)]di-1H-imidazol-2-yl}mercury(II) bis(hexafluoridophosphate) acetonitrile 3.5-solvate

J. Lin and G.-Y. Dong

In the title compound, [Hg(C₅₂H₄₂N₄O₂)](PF₆)₂·3.5CH₃CN, the linear coordination geometry of the Hg ion [C—Hg—C = 174.4 (2)°] is formed by two C atoms from the imidazole fragments [Hg—C = 2.072 (6) and 2.090 (6) Å]. The crystal packing exhibits weak intermolecular C—H

F and C—H

N hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026682/cv2254sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026682/cv2254Isup2.hkl Contains datablock I

CCDC reference: 654698

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.012 Å
Disorder in solvent or counterion
R factor = 0.047
wR factor = 0.127
Data-to-parameter ratio = 15.5

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 ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
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        C53
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C55
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C57
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C59
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       6.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         12
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H17    ..  H60B    ..       2.14 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H54A   ..  H60C    ..       2.12 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         69
            C39 -HG1 -C23 -N2     86.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         70
            C39 -HG1 -C23 -N1    -87.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        113
            C23 -HG1 -C39 -N4    132.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        114
            C23 -HG1 -C39 -N3    -43.00  3.00   1.555   1.555   1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.919
            Tmax scaled      0.719 Tmin scaled      0.583
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         21

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
  12 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

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).

Related literature top

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).

Experimental top

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.

Structure description top

The crystal packing is stabilized by the weak C—H···F and C—H···N interactions (Table 1).

Computing details top

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.

Figures top

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.

{(R)-1,1'-Bis(1-naphthylmethyl)-3,3'-[1,1'-binaphthyl-2,2'- diyldi(oxyethylene)]di-1H-imidazol-2-yl}mercury(II) bis(hexafluoridophosphate) acetonitrile 3.5-solvate top

Crystal data top

[Hg(C₅₂H₄₂N₄O₂)](PF₆)₂·3.5C₂H₃N	Z = 2
M_r = 1389.12	F(000) = 1386
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	11938 independent reflections
Radiation source: fine-focus sealed tube	8762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
phi and ω scans	θ_max = 26.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→11
T_min = 0.634, T_max = 0.782	k = −18→16
17133 measured reflections	l = −20→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0627P)²] where P = (F_o² + 2F_c²)/3
11938 reflections	(Δ/σ)_max = 0.002
770 parameters	Δρ_max = 0.97 e Å⁻³
21 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

[Hg(C₅₂H₄₂N₄O₂)](PF₆)₂·3.5C₂H₃N	γ = 92.066 (7)°
M_r = 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)°

Data collection top

Bruker SMART CCD area-detector diffractometer	11938 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	8762 reflections with I > 2σ(I)
T_min = 0.634, T_max = 0.782	R_int = 0.031
17133 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	21 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	Δρ_max = 0.97 e Å⁻³
11938 reflections	Δρ_min = −0.78 e Å⁻³
770 parameters

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	U_iso*/U_eq	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

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···N6^iv	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
M_r	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)
T_min, T_max	0.634, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	17133, 11938, 8762
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.78

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top

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···N6^iv	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.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page