catena-Poly­[[[diaceto­nitrile­silver(I)]-μ-2,11-di­thia­[3.3]­para­cyclo­phane-κ²S:S′] hydrogeno­cta­fluoro­adipate]

The title compound, {[Ag(C₁₆H₁₆S₂)(C₂H₃N)₂](C₆HF₈O₄)}_n, forms two infinite chains, which are approximately perpendicular to each other. One chain consists of [Ag(C₁₆H₁₆S₂)(C₂H₃N)₂]_nⁿ⁺, and the other is formed from HOFA⁻ (HOFA⁻ is hydrogen octa­fluoro­adipate) units via O_c—H...O_c (c is carboxy) hydrogen-bonding interactions, with an H...A distance of 1.66 (5) Å. Each silver(I) cation lies on a crystallographic twofold rotation axis and has a tetrahedral geometry, defined by two N atoms belonging to two aceto­nitrile mol­ecules and two S atoms from two 2,11-di­thia­[3.3]­para­cyclo­phane mol­ecules. The cyclophanes have inversion symmetry.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.067
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.78 Ratio
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C12

Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          8
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08

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

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

---

Computing details

Data collection: CrystalClear; cell refinement: CrystalClear; data reduction: TEXSAN Ver. 1.11 (TEXSAN, 1999); program(s) used to solve structure: SIR88 (Burla et al., 1989); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN Ver. 1.11; software used to prepare material for publication: TEXSAN Ver. 1.11.

(I)

Crystal data

[Ag(C16H16S2)(C2H3N)2](C6HF8O4)	F(000) = 1504.0
Mr = 751.45	Dx = 1.702 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -C 2yc	Cell parameters from 4112 reflections
a = 8.748 (1) Å	θ = 3.2–27.5°
b = 19.503 (2) Å	µ = 0.91 mm^−1
c = 17.247 (2) Å	T = 150 K
β = 94.842 (5)°	Block, colourless
V = 2932.2 (6) Å^3	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection

Rigaku/MSC Mercury CCD diffractometer	2847 reflections with I > 2σ(I)
Detector resolution: 14.62 pixels mm^-1	Rint = 0.032
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (Jacobson, 1998)	h = −10→11
Tmin = 0.778, Tmax = 0.872	k = −25→24
11413 measured reflections	l = −22→19
3352 independent reflections

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0252P)^2 + 2.7139P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.035	(Δ/σ)max = −0.001
wR(F^2) = 0.067	Δρmax = 0.34 e Å^−3
S = 1.10	Δρmin = −0.36 e Å^−3
2847 reflections	Extinction correction: SHELXL97
223 parameters	Extinction coefficient: none
H atoms treated by a mixture of independent and constrained refinement

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ag1	1.0000	0.45636 (1)	0.7500	0.0327 (1)
S1	0.77210 (6)	0.49623 (3)	0.66707 (3)	0.0240 (1)
F1	0.7320 (2)	0.72386 (9)	0.78062 (8)	0.0421 (4)
F2	0.8006 (2)	0.61744 (8)	0.80364 (8)	0.0469 (4)
F3	1.0345 (2)	0.76246 (7)	0.82251 (7)	0.0324 (3)
F4	1.0958 (2)	0.65452 (8)	0.82779 (8)	0.0357 (4)
O1	0.7551 (2)	0.7447 (1)	0.92958 (9)	0.0347 (4)
O2	0.8954 (2)	0.6496 (1)	0.9523 (1)	0.0389 (4)
N1	0.9114 (4)	0.3708 (1)	0.8316 (2)	0.0637 (8)
C1	0.5153 (2)	0.4280 (1)	0.6012 (1)	0.0221 (5)
C2	0.5003 (3)	0.3967 (1)	0.5293 (1)	0.0275 (5)
C3	0.3821 (3)	0.4144 (1)	0.4742 (1)	0.0286 (5)
C4	0.2769 (2)	0.4643 (1)	0.4899 (1)	0.0211 (5)
C5	0.2855 (3)	0.4921 (1)	0.5640 (1)	0.0272 (5)
C6	0.4033 (3)	0.4738 (1)	0.6191 (1)	0.0299 (6)
C7	0.6592 (3)	0.4170 (1)	0.6548 (2)	0.0265 (5)
C8	0.8431 (3)	0.5097 (1)	0.5716 (1)	0.0245 (5)
C9	0.8299 (3)	0.6926 (1)	0.9106 (1)	0.0256 (5)
C10	0.8348 (3)	0.6836 (1)	0.8217 (1)	0.0263 (5)
C11	0.9938 (3)	0.6999 (1)	0.7946 (1)	0.0218 (5)
C12	0.8942 (3)	0.3270 (2)	0.8709 (2)	0.0392 (6)
C13	0.8718 (4)	0.2711 (2)	0.9223 (2)	0.080 (1)
H1	0.570 (4)	0.366 (1)	0.516 (2)	0.0499*
H2	0.380 (3)	0.395 (1)	0.424 (2)	0.0499*
H3	0.215 (3)	0.526 (2)	0.575 (2)	0.0499*
H4	0.409 (3)	0.495 (1)	0.668 (2)	0.0499*
H5	0.720 (3)	0.383 (2)	0.636 (2)	0.0499*
H6	0.637 (3)	0.409 (1)	0.710 (2)	0.0499*
H7	0.889 (3)	0.468 (2)	0.555 (2)	0.0499*
H8	0.923 (3)	0.544 (2)	0.582 (2)	0.0499*
H9	0.7666	0.2567	0.9159	0.0983*
H10	0.8967	0.2855	0.9750	0.0983*
H11	0.9371	0.2336	0.9104	0.0983*
H12	0.757 (9)	0.749 (4)	0.975 (3)	0.0499*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0303 (2)	0.0310 (2)	0.0331 (2)	0.0000	−0.0191 (1)	0.0000
S1	0.0226 (3)	0.0246 (3)	0.0229 (3)	0.0008 (2)	−0.0100 (2)	−0.0012 (2)
F1	0.0281 (8)	0.074 (1)	0.0237 (7)	0.0098 (8)	−0.0002 (6)	−0.0009 (7)
F2	0.070 (1)	0.0433 (9)	0.0303 (8)	−0.0323 (8)	0.0198 (8)	−0.0157 (7)
F3	0.0406 (8)	0.0312 (8)	0.0258 (7)	−0.0121 (7)	0.0048 (6)	−0.0094 (6)
F4	0.0405 (9)	0.0460 (9)	0.0213 (7)	0.0182 (7)	0.0064 (6)	0.0108 (6)
O1	0.048 (1)	0.035 (1)	0.0227 (9)	0.0017 (9)	0.0123 (9)	−0.0059 (9)
O2	0.049 (1)	0.044 (1)	0.0239 (9)	0.0084 (9)	0.0061 (8)	−0.0008 (8)
N1	0.074 (2)	0.044 (2)	0.072 (2)	−0.008 (1)	0.002 (2)	0.019 (2)
C1	0.019 (1)	0.022 (1)	0.024 (1)	−0.0049 (9)	−0.0036 (9)	0.0065 (9)
C2	0.029 (1)	0.020 (1)	0.032 (1)	0.0048 (10)	−0.007 (1)	0.000 (1)
C3	0.033 (1)	0.023 (1)	0.027 (1)	0.004 (1)	−0.010 (1)	−0.006 (1)
C4	0.018 (1)	0.020 (1)	0.024 (1)	−0.0047 (9)	−0.0056 (8)	0.0021 (9)
C5	0.019 (1)	0.036 (1)	0.027 (1)	0.003 (1)	0.0013 (9)	−0.003 (1)
C6	0.026 (1)	0.043 (2)	0.020 (1)	0.001 (1)	−0.0007 (10)	−0.003 (1)
C7	0.024 (1)	0.024 (1)	0.029 (1)	−0.0010 (10)	−0.0088 (10)	0.004 (1)
C8	0.018 (1)	0.025 (1)	0.029 (1)	0.0017 (10)	−0.0065 (9)	0.000 (1)
C9	0.028 (1)	0.031 (1)	0.019 (1)	−0.008 (1)	0.0071 (9)	−0.005 (1)
C10	0.030 (1)	0.029 (1)	0.020 (1)	−0.006 (1)	0.0048 (10)	−0.0066 (10)
C11	0.027 (1)	0.020 (1)	0.018 (1)	−0.0004 (9)	0.0013 (9)	−0.0014 (9)
C12	0.035 (2)	0.037 (2)	0.046 (2)	−0.005 (1)	−0.002 (1)	0.002 (1)
C13	0.064 (2)	0.090 (3)	0.079 (3)	−0.042 (2)	−0.032 (2)	0.042 (2)

Geometric parameters (Å, º)

Ag1—S1	2.4787 (5)	C4—C8^ii	1.516 (3)
Ag1—S1^i	2.4787 (5)	C5—C6	1.388 (3)
Ag1—N1	2.355 (3)	C9—C10	1.548 (3)
Ag1—N1^i	2.355 (3)	C10—C11	1.537 (3)
S1—C7	1.837 (3)	C11—C11^i	1.550 (4)
S1—C8	1.827 (3)	C12—C13	1.428 (5)
F1—C10	1.348 (3)	O1—H12	0.793
F2—C10	1.355 (3)	C2—H1	0.90 (3)
F3—C11	1.350 (3)	C3—H2	0.94 (3)
F4—C11	1.349 (3)	C5—H3	0.93 (3)
O1—C9	1.266 (3)	C6—H4	0.94 (3)
O2—C9	1.216 (3)	C7—H5	0.93 (3)
N1—C12	1.109 (4)	C7—H6	1.00 (3)
C1—C2	1.379 (3)	C8—H7	0.96 (4)
C1—C6	1.379 (3)	C8—H8	0.97 (3)
C1—C7	1.513 (3)	C13—H9	0.960
C2—C3	1.387 (3)	C13—H10	0.960
C3—C4	1.383 (3)	C13—H11	0.960
C4—C5	1.384 (3)
F1···C12^iii	3.407 (3)	O1···O2^vi	3.254 (3)
F2···C5^iv	3.471 (3)	O1···C13^vii	3.385 (4)
F3···C13^v	3.292 (4)	O2···C13^viii	3.236 (4)
F3···C12^v	3.426 (3)	O2···C5^iv	3.456 (3)
F3···C7^iii	3.496 (3)	O2···C12^viii	3.456 (3)
F3···C1^iii	3.527 (3)	N1···C5^iv	3.511 (4)
O1···C9^vi	3.162 (3)	N1···C6^iv	3.568 (4)
S1—Ag1—S1^i	143.43 (3)	F3—C11—C10	107.2 (2)
S1—Ag1—N1	106.12 (8)	F3—C11—C11^i	108.4 (1)
S1—Ag1—N1^i	99.61 (7)	F4—C11—C10	108.6 (2)
S1^i—Ag1—N1	99.61 (7)	F4—C11—C11^i	108.8 (2)
S1^i—Ag1—N1^i	106.12 (8)	C10—C11—C11^i	116.3 (2)
N1—Ag1—N1^i	89.8 (1)	N1—C12—C13	179.4 (4)
Ag1—S1—C7	101.60 (8)	C9—O1—H12	112.8
Ag1—S1—C8	104.30 (7)	C1—C2—H1	121 (2)
C7—S1—C8	103.7 (1)	C3—C2—H1	118 (2)
Ag1—N1—C12	168.4 (3)	C2—C3—H2	119 (1)
C2—C1—C6	118.2 (2)	C4—C3—H2	120 (1)
C2—C1—C7	119.8 (2)	C4—C5—H3	119 (2)
C6—C1—C7	121.7 (2)	C6—C5—H3	121 (2)
C1—C2—C3	120.9 (2)	C1—C6—H4	120 (1)
C2—C3—C4	120.8 (2)	C5—C6—H4	118 (1)
C3—C4—C5	118.1 (2)	S1—C7—H5	109 (2)
C3—C4—C8^ii	122.1 (2)	S1—C7—H6	99 (1)
C5—C4—C8^ii	119.7 (2)	C1—C7—H5	111 (2)
C4—C5—C6	120.7 (2)	C1—C7—H6	112 (1)
C1—C6—C5	120.9 (2)	H5—C7—H6	113 (3)
S1—C7—C1	111.2 (2)	S1—C8—H7	109 (2)
S1—C8—C4^ii	114.3 (2)	S1—C8—H8	103 (2)
O1—C9—O2	128.9 (2)	C4^ii—C8—H7	111 (2)
O1—C9—C10	113.9 (2)	C4^ii—C8—H8	110 (2)
O2—C9—C10	117.2 (2)	H7—C8—H8	109 (3)
F1—C10—F2	108.0 (2)	C12—C13—H9	109.5
F1—C10—C9	112.4 (2)	C12—C13—H10	109.5
F1—C10—C11	107.5 (2)	C12—C13—H11	109.5
F2—C10—C9	108.1 (2)	H9—C13—H10	109.5
F2—C10—C11	108.3 (2)	H9—C13—H11	109.5
C9—C10—C11	112.3 (2)	H10—C13—H11	109.5
F3—C11—F4	107.2 (2)

Symmetry codes: (i) −x+2, y, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+1, y, −z+3/2; (v) x+1/2, y+1/2, z; (vi) −x+3/2, −y+3/2, −z+2; (vii) x−1/2, y+1/2, z; (viii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H12···O1^vi	0.79 (5)	1.66 (5)	2.447 (3)	175 (10)

Symmetry code: (vi) −x+3/2, −y+3/2, −z+2.