4,5-Di­iodo[1,2,5]­thia­diazo­lotetra­thia­fulvalene

In the crystal structure of the title compound, 5-(4,5-di­iodo-1,3-di­thiol-2-yl­idene)-1,3-di­aza-2,4,6-tri­thia­pentalene, C₆I₂N₂S₅, a large number of short intermolecular heteroatom contacts, such as S...N, S...S, S...I, N...I and I...I, are observed. The mol­ecules, which are planar within 0.051 Å, stack along the b axis in a head-to-head fashion.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.019 Å
• R factor = 0.099
• wR factor = 0.189
• Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT040_ALERT_1_C No H-atoms in this Carbon Containing Compound ..          ?
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         19
PLAT431_ALERT_2_C Short Inter HL..A Contact  I2     ..  N1       =       3.47 Ang.

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   EO
            From the CIF: _chemical_formula_sum :C6 I2 N2 S5

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

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Computing details

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

5-(4,5-diiodo-1,3-dithiol-2-ylidene)-1,3,2,4,6-diazatrithiapentalene

Crystal data

C6I2N2S5	F(000) = 944
Mr = 514.18	Dx = 2.860 Mg m^−3
Monoclinic, P21/n	Melting point: 514 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 12.180 (5) Å	Cell parameters from 3488 reflections
b = 4.8825 (17) Å	θ = 3.0–27.5°
c = 20.083 (8) Å	µ = 6.11 mm^−1
β = 91.152 (9)°	T = 296 K
V = 1194.1 (8) Å^3	Needle, yellow
Z = 4	0.50 × 0.08 × 0.03 mm

Data collection

Rigaku Mercury CCD diffractometer	2709 independent reflections
Radiation source: Rotating Anode	2256 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.078
Detector resolution: 14.62 pixels mm^-1	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −15→14
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)	k = −6→4
Tmin = 0.146, Tmax = 0.836	l = −25→25
11499 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Primary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.099	Secondary atom site location: difference Fourier map
wR(F^2) = 0.189	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 25.5736P] where P = (Fo^2 + 2Fc^2)/3
S = 1.31	(Δ/σ)max < 0.001
2709 reflections	Δρmax = 1.79 e Å^−3
136 parameters	Δρmin = −1.31 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.7545 (0.0177) x + 3.5918 (0.0034) y + 12.7290 (0.0120) z = 3.1941 (0.0043)

* -0.1066 (0.0049) I1 * -0.0517 (0.0051) I2 * 0.0595 (0.0047) S1 * 0.0551 (0.0048) S2 * 0.0560 (0.0049) S3 * 0.0457 (0.0049) S4 * -0.0664 (0.0056) S5 * -0.0104 (0.0106) N1 * -0.0570 (0.0101) N2 * 0.0495 (0.0127) C1 * 0.0133 (0.0117) C2 * -0.0072 (0.0126) C3 * 0.0414 (0.0128) C4 * -0.0027 (0.0122) C5 * -0.0185 (0.0109) C6

Rms deviation of fitted atoms = 0.0506

2.8694 (0.0401) x + 3.6510 (0.0172) y + 12.3692 (0.0947) z = 3.3328 (0.0253)

Angle to previous plane (with approximate e.s.d.) = 1.34 (0.58)

* -0.0166 (0.0062) C1 * 0.0024 (0.0087) C2 * -0.0127 (0.0088) C3 * 0.0100 (0.0062) S1 * 0.0168 (0.0064) S2

Rms deviation of fitted atoms = 0.0128

2.7843 (0.0368) x + 3.4993 (0.0084) y + 13.1369 (0.0338) z = 3.2271 (0.0066)

Angle to previous plane (with approximate e.s.d.) = 2.85 (0.62)

* 0.0052 (0.0069) S3 * 0.0246 (0.0067) S4 * -0.0027 (0.0066) S5 * 0.0132 (0.0088) N1 * -0.0091 (0.0083) N2 * -0.0191 (0.0082) C4 * -0.0046 (0.0118) C5 * -0.0075 (0.0105) C6

Rms deviation of fitted atoms = 0.0129

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
I1	0.17742 (9)	1.3373 (2)	−0.17318 (6)	0.0433 (3)
I2	0.46971 (9)	1.0871 (2)	−0.16153 (6)	0.0453 (3)
S1	0.1502 (3)	0.9473 (8)	−0.04421 (19)	0.0317 (8)
S2	0.3788 (3)	0.7421 (8)	−0.0361 (2)	0.0350 (9)
S3	0.0848 (3)	0.5634 (8)	0.07800 (19)	0.0311 (8)
S4	0.3182 (3)	0.3533 (8)	0.0860 (2)	0.0329 (8)
S5	0.1248 (3)	−0.0179 (8)	0.22376 (19)	0.0330 (8)
N1	0.0503 (10)	0.205 (3)	0.1815 (6)	0.033 (3)
N2	0.2428 (10)	0.026 (2)	0.1865 (6)	0.031 (3)
C1	0.2459 (11)	0.727 (3)	−0.0037 (7)	0.023 (3)
C2	0.2426 (11)	1.069 (3)	−0.1021 (6)	0.025 (3)
C3	0.3450 (11)	0.976 (3)	−0.0997 (7)	0.027 (3)
C4	0.2177 (12)	0.571 (3)	0.0460 (7)	0.027 (3)
C5	0.1144 (11)	0.311 (3)	0.1383 (7)	0.026 (3)
C6	0.2243 (10)	0.215 (3)	0.1403 (6)	0.020 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0408 (6)	0.0437 (6)	0.0453 (7)	0.0029 (5)	0.0024 (5)	0.0140 (5)
I2	0.0355 (6)	0.0523 (7)	0.0488 (7)	−0.0017 (5)	0.0175 (5)	0.0090 (5)
S1	0.0206 (17)	0.037 (2)	0.038 (2)	0.0032 (14)	0.0075 (15)	0.0105 (16)
S2	0.0220 (18)	0.043 (2)	0.040 (2)	0.0024 (15)	0.0115 (16)	0.0136 (17)
S3	0.0224 (17)	0.040 (2)	0.031 (2)	0.0071 (14)	0.0067 (14)	0.0101 (15)
S4	0.0180 (16)	0.043 (2)	0.037 (2)	0.0025 (14)	0.0057 (15)	0.0123 (16)
S5	0.036 (2)	0.034 (2)	0.0292 (19)	−0.0029 (15)	0.0045 (16)	0.0075 (15)
N1	0.034 (7)	0.037 (7)	0.029 (7)	0.003 (5)	0.015 (5)	0.010 (5)
N2	0.027 (6)	0.037 (7)	0.028 (7)	−0.003 (5)	−0.006 (5)	0.010 (5)
C1	0.023 (7)	0.018 (6)	0.030 (7)	−0.005 (5)	0.007 (6)	0.008 (5)
C2	0.030 (7)	0.024 (7)	0.021 (7)	−0.004 (5)	0.007 (6)	0.008 (5)
C3	0.019 (7)	0.034 (8)	0.030 (8)	0.003 (5)	0.008 (6)	0.004 (6)
C4	0.033 (8)	0.025 (7)	0.023 (7)	0.004 (6)	0.004 (6)	−0.002 (5)
C5	0.028 (7)	0.025 (7)	0.027 (7)	0.004 (5)	0.004 (6)	0.000 (5)
C6	0.018 (6)	0.028 (7)	0.014 (6)	−0.004 (5)	−0.006 (5)	−0.002 (5)

Geometric parameters (Å, º)

I1—C2	2.083 (13)	S4—C6	1.734 (13)
I2—C3	2.054 (13)	S5—N1	1.641 (12)
S1—C1	1.771 (14)	S5—N2	1.648 (13)
S1—C2	1.739 (13)	N1—C5	1.288 (17)
S2—C1	1.758 (13)	N2—C6	1.324 (17)
S2—C3	1.756 (14)	C1—C4	1.309 (18)
S3—C4	1.754 (14)	C2—C3	1.327 (19)
S3—C5	1.761 (14)	C5—C6	1.417 (18)
S4—C4	1.796 (14)
I1···N1^i	3.564 (12)	S3···S5^vi	3.596 (6)
I1···S3^i	3.786 (4)	S4···I2^iv	3.666 (4)
I1···I2^ii	3.934 (2)	S5···N2^vii	3.269 (13)
I2···N1^iii	3.473 (12)	S5···I2^viii	3.670 (4)
I2···N2^iv	3.590 (12)	S5···S3^ix	3.596 (6)
I2···S5^iii	3.670 (4)	N1···I2^viii	3.473 (12)
I2···S4^iv	3.666 (4)	N1···I1^i	3.564 (12)
I2···I1^v	3.934 (2)	N2···S5^x	3.269 (13)
S3···I1^i	3.786 (4)	N2···I2^iv	3.590 (12)
C2—S1—C1	94.9 (6)	C2—C3—S2	117.1 (10)
C1—S2—C3	95.3 (6)	C2—C3—I2	126.4 (10)
C4—S3—C5	95.1 (6)	S2—C3—I2	116.5 (7)
C6—S4—C4	93.5 (6)	C1—C4—S3	123.3 (11)
N2—S5—N1	99.1 (6)	C1—C4—S4	120.0 (11)
C5—N1—S5	106.1 (10)	S3—C4—S4	116.7 (8)
C6—N2—S5	105.7 (9)	N1—C5—C6	115.7 (12)
C4—C1—S2	124.3 (11)	N1—C5—S3	128.8 (11)
C4—C1—S1	121.6 (11)	C6—C5—S3	115.5 (10)
S2—C1—S1	114.0 (7)	N2—C6—C5	113.4 (12)
C3—C2—S1	118.6 (10)	N2—C6—S4	127.4 (10)
C3—C2—I1	125.8 (10)	C5—C6—S4	119.2 (10)
S1—C2—I1	115.5 (7)
N2—S5—N1—C5	0.9 (12)	S1—C1—C4—S4	−179.5 (7)
N1—S5—N2—C6	−0.4 (11)	C5—S3—C4—C1	178.8 (13)
C3—S2—C1—C4	177.6 (13)	C5—S3—C4—S4	−2.4 (9)
C3—S2—C1—S1	−2.5 (9)	C6—S4—C4—C1	−178.3 (12)
C2—S1—C1—C4	−178.2 (13)	C6—S4—C4—S3	2.7 (9)
C2—S1—C1—S2	1.9 (9)	S5—N1—C5—C6	−1.1 (16)
C1—S1—C2—C3	−0.3 (13)	S5—N1—C5—S3	−179.8 (9)
C1—S1—C2—I1	176.6 (7)	C4—S3—C5—N1	179.6 (14)
S1—C2—C3—S2	−1.5 (17)	C4—S3—C5—C6	0.9 (11)
I1—C2—C3—S2	−178.0 (7)	S5—N2—C6—C5	−0.2 (14)
S1—C2—C3—I2	−179.6 (8)	S5—N2—C6—S4	178.5 (8)
I1—C2—C3—I2	4 (2)	N1—C5—C6—N2	0.8 (18)
C1—S2—C3—C2	2.4 (13)	S3—C5—C6—N2	179.7 (10)
C1—S2—C3—I2	−179.3 (8)	N1—C5—C6—S4	−177.9 (10)
S2—C1—C4—S3	179.2 (8)	S3—C5—C6—S4	1.0 (15)
S1—C1—C4—S3	−0.6 (18)	C4—S4—C6—N2	179.3 (12)
S2—C1—C4—S4	0.4 (18)	C4—S4—C6—C5	−2.2 (11)

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