Bis­[2-(1-methyl-1H-imidazol-2-yl-3-iosulfanyl)-6-(1-methyl-1H-imidazol-2-yl­sulfanyl)­pyridine] tetra­chloro­ferrate tetra­fluoro­borate

The cations of the title complex, [H-{2,6-(meth)₂py}]₂[FeCl₄][BF₄] or (C₁₃H₁₄N₅S₂)₂[FeCl₄]BF₄, form dimers of protonated 2,6-bis(1-methyl-1H-imidazol-2-yl­sulfanyl)­pyridine mol­ecules, which are held together by moderate N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.049
• wR factor = 0.095
• Data-to-parameter ratio = 18.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           29.04
         From the CIF: _reflns_number_total               8426
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns        10005
         Completeness (_total/calc)             84.22%
          Alert A: < 85% complete (theta max?)


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).

(I)

Crystal data

2C13H14N5S2^+·FeCl4^−·BF4^−	Z = 2
Mr = 893.28	F(000) = 906
Triclinic, P1	Dx = 1.585 Mg m^−3
a = 9.0531 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.2213 (14) Å	Cell parameters from 391 reflections
c = 16.0249 (18) Å	θ = 1.9–27.6°
α = 82.51 (2)°	µ = 0.97 mm^−1
β = 82.04 (3)°	T = 150 K
γ = 82.82 (2)°	Laths, yellow
V = 1872.2 (4) Å^3	0.41 × 0.14 × 0.04 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	8426 independent reflections
Radiation source: fine-focus sealed tube	4004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 29.0°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements) (SAINT; Bruker, 2001)	h = −12→10
Tmin = 0.693, Tmax = 0.960	k = −17→17
10005 measured reflections	l = −21→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0259P)^2] where P = (Fo^2 + 2Fc^2)/3
8426 reflections	(Δ/σ)max = 0.011
455 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.36 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.

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.68652 (6)	0.77219 (4)	−0.14729 (4)	0.03317 (17)
B1	0.6173 (5)	0.2179 (4)	−0.5376 (3)	0.0330 (12)
F1	0.5351 (3)	0.31080 (19)	−0.5321 (2)	0.0922 (11)
F2	0.7115 (3)	0.2027 (2)	−0.47664 (16)	0.0778 (9)
F3	0.5237 (3)	0.14138 (18)	−0.52527 (14)	0.0568 (7)
F4	0.7004 (2)	0.21793 (18)	−0.61535 (14)	0.0568 (7)
S1	−0.16677 (10)	0.46757 (8)	−0.33385 (6)	0.0319 (3)
S2	0.21598 (11)	0.37644 (8)	−0.09992 (6)	0.0340 (3)
S3	−0.18660 (11)	0.17965 (8)	−0.29057 (7)	0.0403 (3)
S4	0.25497 (11)	0.06824 (8)	−0.09325 (6)	0.0344 (3)
Cl1	0.64597 (11)	0.75116 (8)	−0.27521 (7)	0.0460 (3)
Cl2	0.52787 (11)	0.68869 (8)	−0.05549 (7)	0.0461 (3)
Cl3	0.92252 (10)	0.71850 (8)	−0.13357 (7)	0.0426 (3)
Cl4	0.64874 (12)	0.93497 (8)	−0.12944 (7)	0.0479 (3)
N1	0.1013 (3)	0.3917 (2)	−0.41644 (19)	0.0350 (8)
H1N	0.0811	0.3291	−0.4099	0.042*
N2	0.0815 (3)	0.5560 (2)	−0.41086 (19)	0.0328 (8)
N3	0.0111 (3)	0.4273 (2)	−0.20972 (19)	0.0257 (7)
N4	0.4101 (3)	0.3318 (2)	−0.2395 (2)	0.0284 (8)
N5	0.3510 (3)	0.4978 (2)	−0.23316 (19)	0.0280 (8)
N6	0.0679 (3)	0.1919 (2)	−0.4042 (2)	0.0351 (8)
N7	−0.0005 (4)	0.0353 (3)	−0.3734 (2)	0.0378 (9)
N8	0.0222 (3)	0.1233 (2)	−0.18369 (19)	0.0288 (8)
N9	0.3367 (3)	−0.0242 (2)	−0.23941 (19)	0.0261 (7)
N10	0.4017 (3)	0.1289 (2)	−0.24880 (19)	0.0294 (8)
H10N	0.4117	0.1890	−0.2369	0.035*
C1	0.2287 (4)	0.4275 (4)	−0.4589 (2)	0.0416 (11)
H1A	0.3097	0.3884	−0.4857	0.050*
C2	0.2171 (4)	0.5292 (4)	−0.4555 (3)	0.0438 (12)
H2A	0.2882	0.5732	−0.4791	0.053*
C3	0.0208 (4)	0.6594 (3)	−0.3915 (3)	0.0459 (12)
H3A	−0.0852	0.6689	−0.3948	0.069*
H3B	0.0691	0.7091	−0.4317	0.069*
H3C	0.0386	0.6680	−0.3353	0.069*
C4	0.0141 (4)	0.4703 (3)	−0.3870 (2)	0.0293 (9)
C5	−0.1310 (4)	0.4526 (3)	−0.2266 (2)	0.0266 (9)
C6	−0.2523 (4)	0.4665 (3)	−0.1653 (2)	0.0304 (10)
H6A	−0.3486	0.4858	−0.1800	0.036*
C7	−0.2264 (4)	0.4510 (3)	−0.0820 (2)	0.0332 (10)
H7A	−0.3060	0.4589	−0.0391	0.040*
C8	−0.0831 (4)	0.4238 (3)	−0.0617 (2)	0.0294 (9)
H8A	−0.0637	0.4130	−0.0056	0.035*
C9	0.0316 (4)	0.4131 (3)	−0.1281 (2)	0.0261 (9)
C10	0.3269 (4)	0.4023 (3)	−0.1966 (2)	0.0249 (9)
C11	0.4862 (4)	0.3856 (3)	−0.3070 (2)	0.0320 (10)
H11A	0.5531	0.3560	−0.3487	0.038*
C12	0.4508 (4)	0.4879 (3)	−0.3049 (2)	0.0329 (10)
H12A	0.4868	0.5404	−0.3439	0.040*
C13	0.2831 (4)	0.5957 (3)	−0.2037 (3)	0.0438 (12)
H13A	0.3040	0.5980	−0.1469	0.066*
H13B	0.1765	0.6019	−0.2046	0.066*
H13C	0.3244	0.6514	−0.2404	0.066*
C14	0.1635 (4)	0.1272 (3)	−0.4516 (3)	0.0407 (11)
H14A	0.2447	0.1463	−0.4901	0.049*
C15	0.1225 (4)	0.0308 (3)	−0.4340 (3)	0.0408 (11)
H15A	0.1687	−0.0271	−0.4583	0.049*
C16	−0.0824 (5)	−0.0504 (3)	−0.3349 (3)	0.0578 (14)
H16A	−0.1031	−0.0480	−0.2747	0.087*
H16B	−0.0231	−0.1138	−0.3460	0.087*
H16C	−0.1752	−0.0461	−0.3585	0.087*
C17	−0.0309 (4)	0.1350 (3)	−0.3572 (2)	0.0311 (10)
C18	−0.1205 (4)	0.1598 (3)	−0.1899 (2)	0.0293 (10)
C19	−0.2236 (4)	0.1856 (3)	−0.1219 (3)	0.0376 (11)
H19A	−0.3225	0.2098	−0.1292	0.045*
C20	−0.1760 (5)	0.1747 (3)	−0.0436 (3)	0.0451 (12)
H20A	−0.2426	0.1917	0.0034	0.054*
C21	−0.0279 (5)	0.1380 (3)	−0.0344 (2)	0.0371 (11)
H21A	0.0072	0.1303	0.0182	0.045*
C22	0.0650 (4)	0.1136 (3)	−0.1064 (3)	0.0287 (9)
C23	0.3303 (4)	0.0583 (3)	−0.1976 (2)	0.0243 (9)
C24	0.4564 (4)	0.0907 (3)	−0.3231 (2)	0.0322 (10)
H24A	0.5111	0.1246	−0.3695	0.039*
C25	0.4171 (4)	−0.0049 (3)	−0.3172 (2)	0.0329 (10)
H25A	0.4404	−0.0496	−0.3586	0.039*
C26	0.2684 (4)	−0.1175 (3)	−0.2060 (2)	0.0406 (11)
H26A	0.1668	−0.0999	−0.1818	0.061*
H26B	0.3243	−0.1553	−0.1631	0.061*
H26C	0.2691	−0.1589	−0.2511	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0282 (3)	0.0357 (4)	0.0349 (4)	0.0015 (3)	−0.0062 (3)	−0.0038 (3)
B1	0.030 (3)	0.034 (3)	0.034 (3)	−0.006 (2)	0.007 (2)	−0.010 (2)
F1	0.067 (2)	0.0539 (18)	0.150 (3)	0.0120 (15)	0.0147 (19)	−0.0372 (19)
F2	0.073 (2)	0.120 (2)	0.0469 (18)	−0.0387 (18)	−0.0273 (15)	0.0115 (17)
F3	0.0657 (17)	0.0691 (17)	0.0410 (16)	−0.0361 (14)	0.0085 (13)	−0.0141 (13)
F4	0.0525 (16)	0.0838 (19)	0.0375 (16)	−0.0309 (14)	0.0117 (12)	−0.0153 (14)
S1	0.0208 (5)	0.0474 (7)	0.0285 (6)	−0.0051 (5)	−0.0023 (4)	−0.0072 (5)
S2	0.0290 (6)	0.0427 (6)	0.0285 (6)	0.0028 (5)	−0.0060 (5)	−0.0016 (5)
S3	0.0270 (6)	0.0518 (7)	0.0400 (7)	0.0036 (5)	−0.0035 (5)	−0.0057 (6)
S4	0.0406 (6)	0.0375 (6)	0.0250 (6)	−0.0009 (5)	−0.0053 (5)	−0.0053 (5)
Cl1	0.0451 (7)	0.0534 (7)	0.0417 (7)	0.0033 (6)	−0.0123 (5)	−0.0149 (6)
Cl2	0.0302 (6)	0.0534 (7)	0.0502 (8)	−0.0020 (5)	−0.0002 (5)	0.0028 (6)
Cl3	0.0290 (6)	0.0496 (7)	0.0469 (7)	0.0031 (5)	−0.0071 (5)	−0.0009 (5)
Cl4	0.0572 (7)	0.0372 (6)	0.0506 (8)	0.0059 (5)	−0.0161 (6)	−0.0101 (5)
N1	0.0262 (19)	0.047 (2)	0.033 (2)	−0.0058 (17)	−0.0038 (16)	−0.0082 (17)
N2	0.0226 (18)	0.047 (2)	0.030 (2)	−0.0103 (17)	−0.0042 (15)	−0.0028 (17)
N3	0.0241 (18)	0.0265 (18)	0.027 (2)	−0.0012 (14)	−0.0034 (15)	−0.0066 (15)
N4	0.0185 (17)	0.0310 (19)	0.035 (2)	−0.0019 (15)	−0.0026 (15)	−0.0040 (16)
N5	0.0231 (18)	0.0265 (19)	0.035 (2)	−0.0012 (15)	−0.0080 (15)	−0.0025 (16)
N6	0.0243 (18)	0.050 (2)	0.030 (2)	0.0034 (17)	−0.0022 (15)	−0.0087 (18)
N7	0.038 (2)	0.041 (2)	0.034 (2)	0.0035 (18)	−0.0113 (17)	−0.0037 (18)
N8	0.0293 (19)	0.0291 (19)	0.027 (2)	−0.0039 (15)	0.0018 (15)	−0.0057 (15)
N9	0.0276 (18)	0.0271 (18)	0.026 (2)	−0.0014 (15)	−0.0090 (15)	−0.0067 (15)
N10	0.0301 (19)	0.0306 (19)	0.029 (2)	−0.0040 (15)	−0.0055 (15)	−0.0042 (16)
C1	0.022 (2)	0.074 (3)	0.029 (3)	−0.006 (2)	−0.0031 (19)	−0.009 (2)
C2	0.023 (2)	0.074 (3)	0.037 (3)	−0.020 (2)	−0.003 (2)	−0.005 (3)
C3	0.047 (3)	0.049 (3)	0.044 (3)	−0.012 (2)	−0.010 (2)	−0.004 (2)
C4	0.022 (2)	0.046 (3)	0.022 (2)	−0.007 (2)	−0.0050 (17)	−0.007 (2)
C5	0.028 (2)	0.025 (2)	0.029 (2)	−0.0083 (18)	−0.0022 (18)	−0.0070 (18)
C6	0.025 (2)	0.031 (2)	0.034 (3)	−0.0014 (18)	−0.0030 (19)	−0.005 (2)
C7	0.025 (2)	0.038 (2)	0.034 (3)	−0.0029 (19)	0.0033 (19)	−0.004 (2)
C8	0.036 (2)	0.030 (2)	0.021 (2)	−0.0010 (19)	−0.0005 (18)	−0.0020 (18)
C9	0.024 (2)	0.021 (2)	0.032 (3)	−0.0022 (17)	−0.0026 (18)	−0.0033 (18)
C10	0.021 (2)	0.027 (2)	0.026 (2)	0.0005 (17)	−0.0062 (17)	0.0007 (18)
C11	0.021 (2)	0.039 (3)	0.036 (3)	−0.0017 (19)	−0.0032 (18)	−0.005 (2)
C12	0.019 (2)	0.042 (3)	0.035 (3)	−0.0082 (19)	−0.0061 (18)	0.010 (2)
C13	0.038 (3)	0.031 (2)	0.063 (3)	0.002 (2)	−0.012 (2)	−0.009 (2)
C14	0.031 (2)	0.058 (3)	0.031 (3)	0.004 (2)	−0.0030 (19)	−0.007 (2)
C15	0.031 (2)	0.055 (3)	0.036 (3)	0.015 (2)	−0.007 (2)	−0.016 (2)
C16	0.069 (3)	0.045 (3)	0.058 (4)	−0.005 (3)	−0.009 (3)	−0.005 (3)
C17	0.025 (2)	0.039 (3)	0.029 (2)	0.004 (2)	−0.0082 (18)	−0.007 (2)
C18	0.031 (2)	0.024 (2)	0.033 (3)	−0.0042 (18)	−0.0027 (19)	−0.0056 (19)
C19	0.035 (2)	0.033 (2)	0.042 (3)	0.003 (2)	0.004 (2)	−0.008 (2)
C20	0.047 (3)	0.041 (3)	0.041 (3)	0.001 (2)	0.015 (2)	−0.010 (2)
C21	0.051 (3)	0.035 (2)	0.024 (2)	0.000 (2)	0.003 (2)	−0.008 (2)
C22	0.037 (2)	0.017 (2)	0.033 (3)	−0.0042 (18)	−0.002 (2)	−0.0038 (19)
C23	0.020 (2)	0.028 (2)	0.025 (2)	0.0012 (17)	−0.0049 (17)	−0.0048 (19)
C24	0.027 (2)	0.046 (3)	0.022 (2)	−0.001 (2)	−0.0039 (18)	−0.002 (2)
C25	0.030 (2)	0.040 (3)	0.028 (3)	0.001 (2)	−0.0020 (19)	−0.009 (2)
C26	0.047 (3)	0.034 (2)	0.042 (3)	−0.006 (2)	−0.001 (2)	−0.009 (2)

Geometric parameters (Å, º)

Fe1—Cl4	2.1864 (12)	N5—C12	1.370 (4)
Fe1—Cl1	2.1902 (12)	N5—C13	1.469 (4)
Fe1—Cl3	2.1972 (11)	N6—C17	1.330 (4)
Fe1—Cl2	2.1983 (11)	N6—C14	1.364 (4)
B1—F1	1.361 (5)	N7—C17	1.363 (4)
B1—F2	1.364 (5)	N7—C15	1.373 (4)
B1—F4	1.363 (5)	N7—C16	1.455 (5)
B1—F3	1.377 (5)	N8—C18	1.333 (4)
S1—C4	1.740 (4)	N8—C22	1.334 (5)
S1—C5	1.774 (4)	N9—C23	1.344 (4)
S2—C10	1.744 (4)	N9—C25	1.365 (4)
S2—C9	1.782 (4)	N9—C26	1.456 (4)
S3—C17	1.736 (4)	N10—C23	1.328 (4)
S3—C18	1.775 (4)	N10—C24	1.359 (4)
S4—C23	1.732 (4)	C1—C2	1.343 (5)
S4—C22	1.781 (4)	C5—C6	1.379 (4)
N1—C4	1.321 (4)	C6—C7	1.373 (5)
N1—C1	1.361 (4)	C7—C8	1.373 (5)
N2—C4	1.340 (4)	C8—C9	1.389 (4)
N2—C2	1.363 (4)	C11—C12	1.354 (5)
N2—C3	1.464 (4)	C14—C15	1.355 (5)
N3—C9	1.332 (4)	C18—C19	1.383 (5)
N3—C5	1.343 (4)	C19—C20	1.366 (5)
N4—C10	1.325 (4)	C20—C21	1.389 (5)
N4—C11	1.365 (4)	C21—C22	1.381 (5)
N5—C10	1.351 (4)	C24—C25	1.343 (5)
Cl4—Fe1—Cl1	110.14 (5)	N1—C4—N2	109.2 (3)
Cl4—Fe1—Cl3	107.96 (5)	N1—C4—S1	126.3 (3)
Cl1—Fe1—Cl3	108.36 (4)	N2—C4—S1	124.3 (3)
Cl4—Fe1—Cl2	108.92 (4)	N3—C5—C6	124.0 (4)
Cl1—Fe1—Cl2	108.23 (5)	N3—C5—S1	118.6 (3)
Cl3—Fe1—Cl2	113.23 (5)	C6—C5—S1	117.4 (3)
F1—B1—F2	108.3 (4)	C7—C6—C5	117.8 (4)
F1—B1—F4	109.4 (4)	C6—C7—C8	120.2 (3)
F2—B1—F4	109.1 (4)	C7—C8—C9	117.6 (4)
F1—B1—F3	110.0 (4)	N3—C9—C8	124.1 (3)
F2—B1—F3	109.8 (4)	N3—C9—S2	119.3 (3)
F4—B1—F3	110.2 (4)	C8—C9—S2	116.6 (3)
C4—S1—C5	101.14 (18)	N4—C10—N5	110.9 (3)
C10—S2—C9	101.97 (17)	N4—C10—S2	124.8 (3)
C17—S3—C18	102.64 (18)	N5—C10—S2	124.0 (3)
C23—S4—C22	100.61 (18)	C12—C11—N4	110.8 (3)
C4—N1—C1	107.8 (3)	C11—C12—N5	105.4 (3)
C4—N2—C2	107.7 (3)	C15—C14—N6	109.7 (4)
C4—N2—C3	126.1 (3)	C14—C15—N7	106.7 (4)
C2—N2—C3	126.3 (3)	N6—C17—N7	110.3 (3)
C9—N3—C5	116.4 (3)	N6—C17—S3	126.1 (3)
C10—N4—C11	105.2 (3)	N7—C17—S3	123.4 (3)
C10—N5—C12	107.6 (3)	N8—C18—C19	124.1 (4)
C10—N5—C13	127.4 (3)	N8—C18—S3	119.7 (3)
C12—N5—C13	125.0 (3)	C19—C18—S3	116.2 (3)
C17—N6—C14	106.4 (3)	C20—C19—C18	118.1 (4)
C17—N7—C15	106.8 (3)	C19—C20—C21	119.8 (4)
C17—N7—C16	127.0 (3)	C22—C21—C20	117.3 (4)
C15—N7—C16	126.1 (4)	N8—C22—C21	124.5 (4)
C18—N8—C22	116.3 (3)	N8—C22—S4	119.1 (3)
C23—N9—C25	108.4 (3)	C21—C22—S4	116.4 (3)
C23—N9—C26	124.9 (3)	N10—C23—N9	107.7 (3)
C25—N9—C26	126.6 (3)	N10—C23—S4	125.7 (3)
C23—N10—C24	109.0 (3)	N9—C23—S4	126.4 (3)
C2—C1—N1	108.1 (4)	C25—C24—N10	107.5 (3)
C1—C2—N2	107.2 (4)	C24—C25—N9	107.3 (3)