Crystal structure of cyclo-tris­(μ-3,4,5,6-tetra­fluoro-o-phenyl­ene-κ²C¹:C²)trimercury–tetra­cyano­ethyl­ene (1/1)

The crystal structure and thermal properties of a mixed-stack donor–acceptor complex of trimeric perfluoro-o-phenyl­ene mercury with tetra­cyano­ethyl­ene in an 1:1 ratio were studied by X-ray diffraction and TGA methods.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.023
• wR factor = 0.055
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...         10 Report
PLAT971_ALERT_2_C Check Calcd Residual Density  0.80A From     Hg1       1.82 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density  1.24A From      C9      -1.65 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.96A From      N1       0.55 eA-3
PLAT975_ALERT_2_C Check Calcd Residual Density  0.97A From      N1       0.50 eA-3

Alert level G
CHEMS02_ALERT_1_G  Please check that you have entered the correct
            _publ_requested_category classification of your compound;
            FI or CI or EI for inorganic; FM or CM or EM for metal-organic;
            FO or CO or EO for organic.
            From the CIF: _publ_requested_category   EM
            From the CIF: _chemical_formula_sum:C24 F12 Hg3 N4
PLAT040_ALERT_1_G No H-atoms in this Carbon Containing Compound ..     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      19.10 Why ?
PLAT432_ALERT_2_G Short Inter X...Y Contact  F2     ..  C11     ..       2.86 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  F5     ..  C12     ..       2.85 Ang.
PLAT432_ALERT_2_G Short Inter X...Y Contact  F6     ..  C11     ..       2.93 Ang.
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

cyclo-Tris(µ-3,4,5,6-tetrafluoro-o-phenylene-κ²C¹:C²)trimercury–tetracyanoethylene (1/1)

Crystal data

[Hg3(C6F4)3]·C6N4	F(000) = 2080
Mr = 1174.05	Dx = 3.193 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5658 (11) Å	Cell parameters from 9624 reflections
b = 13.8297 (15) Å	θ = 4.4–32.7°
c = 16.7166 (18) Å	µ = 18.93 mm^−1
β = 90.575 (1)°	T = 100 K
V = 2442.5 (5) Å^3	Prism, light-yellow
Z = 4	0.15 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	3404 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
φ and ω scans	θmax = 30.0°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
Tmin = 0.150, Tmax = 0.250	k = −19→19
13813 measured reflections	l = −23→23
3560 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Secondary atom site location: difference Fourier map
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0191P)^2 + 19.1P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
3560 reflections	Δρmax = 1.78 e Å^−3
195 parameters	Δρmin = −1.70 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Hg1	0.5000	0.83281 (2)	0.2500	0.01573 (6)
Hg2	0.36631 (2)	0.60249 (2)	0.31557 (2)	0.01493 (5)
F1	0.3423 (3)	0.9966 (2)	0.33993 (17)	0.0259 (6)
F2	0.1469 (3)	0.98904 (19)	0.44275 (17)	0.0267 (6)
F3	0.0409 (3)	0.8182 (2)	0.48130 (17)	0.0253 (5)
F4	0.1388 (3)	0.65100 (19)	0.42523 (17)	0.0247 (5)
F5	0.3016 (3)	0.38265 (19)	0.35217 (16)	0.0240 (5)
F6	0.4034 (3)	0.21483 (18)	0.30301 (17)	0.0238 (5)
C1	0.3490 (4)	0.8248 (3)	0.3293 (3)	0.0186 (7)
C2	0.2968 (4)	0.9087 (3)	0.3601 (3)	0.0198 (8)
C3	0.1952 (4)	0.9069 (3)	0.4121 (3)	0.0199 (8)
C4	0.1415 (4)	0.8193 (3)	0.4332 (3)	0.0191 (8)
C5	0.1927 (4)	0.7350 (3)	0.4030 (2)	0.0177 (7)
C6	0.2958 (4)	0.7350 (3)	0.3517 (2)	0.0153 (7)
C7	0.4474 (4)	0.4743 (3)	0.2765 (2)	0.0161 (7)
C8	0.4008 (4)	0.3863 (3)	0.3008 (2)	0.0173 (7)
C9	0.4501 (4)	0.2987 (3)	0.2762 (3)	0.0189 (8)
N1	0.6254 (4)	0.6785 (3)	0.3521 (2)	0.0213 (7)
N2	0.9176 (4)	0.5836 (3)	0.5355 (3)	0.0289 (8)
C10	0.7588 (4)	0.7081 (3)	0.4799 (2)	0.0165 (7)
C11	0.6861 (4)	0.6895 (3)	0.4081 (2)	0.0174 (7)
C12	0.8478 (4)	0.6369 (3)	0.5080 (2)	0.0198 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.01452 (9)	0.01481 (10)	0.01793 (10)	0.000	0.00398 (7)	0.000
Hg2	0.01430 (7)	0.01349 (8)	0.01709 (8)	0.00109 (4)	0.00400 (5)	0.00000 (5)
F1	0.0273 (13)	0.0178 (12)	0.0327 (14)	−0.0010 (10)	0.0092 (11)	0.0003 (10)
F2	0.0296 (14)	0.0186 (13)	0.0321 (14)	0.0050 (10)	0.0088 (11)	−0.0055 (10)
F3	0.0209 (12)	0.0275 (14)	0.0277 (13)	0.0033 (10)	0.0111 (10)	−0.0001 (11)
F4	0.0243 (13)	0.0192 (12)	0.0308 (14)	−0.0003 (10)	0.0110 (10)	0.0012 (10)
F5	0.0237 (13)	0.0204 (13)	0.0281 (13)	−0.0003 (10)	0.0139 (10)	0.0032 (10)
F6	0.0251 (13)	0.0132 (12)	0.0333 (14)	−0.0026 (9)	0.0073 (11)	0.0029 (10)
C1	0.0174 (18)	0.0188 (19)	0.0195 (18)	0.0010 (14)	0.0016 (14)	0.0010 (14)
C2	0.0200 (19)	0.0171 (19)	0.0225 (19)	0.0003 (14)	0.0045 (15)	−0.0001 (15)
C3	0.0190 (18)	0.0184 (19)	0.0223 (19)	0.0091 (14)	0.0018 (15)	−0.0041 (15)
C4	0.0142 (17)	0.023 (2)	0.0206 (18)	0.0024 (14)	0.0054 (14)	−0.0003 (15)
C5	0.0181 (18)	0.0180 (18)	0.0171 (17)	0.0014 (14)	0.0023 (14)	0.0010 (14)
C6	0.0142 (16)	0.0158 (18)	0.0161 (17)	0.0034 (13)	0.0031 (13)	−0.0007 (13)
C7	0.0148 (17)	0.0149 (17)	0.0186 (17)	0.0038 (13)	0.0053 (14)	0.0002 (14)
C8	0.0159 (17)	0.0188 (19)	0.0173 (17)	0.0026 (14)	0.0035 (14)	0.0019 (14)
C9	0.0177 (18)	0.0161 (18)	0.0228 (19)	−0.0020 (14)	0.0001 (15)	0.0018 (15)
N1	0.0216 (17)	0.0193 (17)	0.0231 (17)	−0.0011 (13)	0.0044 (13)	0.0001 (13)
N2	0.028 (2)	0.028 (2)	0.031 (2)	0.0051 (16)	0.0072 (16)	0.0016 (16)
C10	0.0143 (16)	0.0169 (18)	0.0184 (17)	−0.0012 (13)	0.0030 (13)	0.0010 (14)
C11	0.0182 (18)	0.0166 (18)	0.0174 (17)	−0.0001 (14)	0.0036 (14)	−0.0011 (14)
C12	0.0196 (18)	0.0195 (19)	0.0205 (18)	0.0001 (15)	0.0030 (14)	−0.0006 (15)

Geometric parameters (Å, º)

Hg1—C1	2.087 (4)	C2—C3	1.389 (6)
Hg1—N1	3.030 (4)	C3—C4	1.385 (6)
Hg2—C6	2.071 (4)	C4—C5	1.382 (6)
Hg2—C7	2.077 (4)	C5—C6	1.394 (5)
Hg2—N1	2.990 (4)	C7—C8	1.375 (6)
F1—C2	1.351 (5)	C7—C7^i	1.429 (7)
F2—C3	1.348 (5)	C8—C9	1.384 (6)
F3—C4	1.340 (4)	C9—C9^i	1.377 (8)
F4—C5	1.347 (5)	N1—C11	1.140 (6)
F5—C8	1.363 (5)	N2—C12	1.136 (6)
F6—C9	1.339 (5)	C10—C10^ii	1.355 (8)
C1—C2	1.387 (6)	C10—C12	1.437 (6)
C1—C6	1.415 (6)	C10—C11	1.441 (6)
C1—Hg1—C1^i	173.9 (2)	C1—C6—Hg2	123.7 (3)
C6—Hg2—C7	176.24 (16)	C8—C7—C7^i	117.8 (2)
C2—C1—C6	118.4 (4)	C8—C7—Hg2	120.8 (3)
C2—C1—Hg1	120.0 (3)	C7^i—C7—Hg2	121.39 (11)
C6—C1—Hg1	121.6 (3)	F5—C8—C7	119.9 (3)
F1—C2—C1	121.1 (4)	F5—C8—C9	116.7 (4)
F1—C2—C3	116.8 (4)	C7—C8—C9	123.4 (4)
C1—C2—C3	122.1 (4)	F6—C9—C9^i	120.0 (2)
F2—C3—C4	118.9 (4)	F6—C9—C8	121.2 (4)
F2—C3—C2	121.4 (4)	C9^i—C9—C8	118.8 (2)
C4—C3—C2	119.7 (4)	C11—N1—Hg2	136.2 (3)
F3—C4—C5	121.7 (4)	C11—N1—Hg1	127.4 (3)
F3—C4—C3	119.5 (4)	Hg2—N1—Hg1	74.82 (9)
C5—C4—C3	118.9 (4)	C10^ii—C10—C12	121.1 (5)
F4—C5—C4	117.3 (4)	C10^ii—C10—C11	119.4 (5)
F4—C5—C6	120.3 (4)	C12—C10—C11	119.5 (4)
C4—C5—C6	122.4 (4)	N1—C11—C10	176.9 (5)
C5—C6—C1	118.6 (4)	N2—C12—C10	175.2 (5)
C5—C6—Hg2	117.7 (3)
C6—C1—C2—F1	−179.0 (4)	F4—C5—C6—C1	179.4 (4)
Hg1—C1—C2—F1	−0.2 (6)	C4—C5—C6—C1	−0.6 (6)
C6—C1—C2—C3	0.3 (6)	F4—C5—C6—Hg2	−2.5 (5)
Hg1—C1—C2—C3	179.1 (3)	C4—C5—C6—Hg2	177.5 (3)
F1—C2—C3—F2	−1.9 (6)	C2—C1—C6—C5	0.7 (6)
C1—C2—C3—F2	178.8 (4)	Hg1—C1—C6—C5	−178.1 (3)
F1—C2—C3—C4	177.9 (4)	C2—C1—C6—Hg2	−177.2 (3)
C1—C2—C3—C4	−1.4 (7)	Hg1—C1—C6—Hg2	4.0 (5)
F2—C3—C4—F3	2.0 (6)	C7^i—C7—C8—F5	179.2 (4)
C2—C3—C4—F3	−177.8 (4)	Hg2—C7—C8—F5	−1.1 (5)
F2—C3—C4—C5	−178.7 (4)	C7^i—C7—C8—C9	−0.4 (7)
C2—C3—C4—C5	1.5 (6)	Hg2—C7—C8—C9	179.3 (3)
F3—C4—C5—F4	−1.2 (6)	F5—C8—C9—F6	−1.2 (6)
C3—C4—C5—F4	179.5 (4)	C7—C8—C9—F6	178.4 (4)
F3—C4—C5—C6	178.8 (4)	F5—C8—C9—C9^i	179.5 (5)
C3—C4—C5—C6	−0.5 (6)	C7—C8—C9—C9^i	−0.8 (8)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+3/2, −y+3/2, −z+1.