Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027558/ob6574sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027558/ob6574Isup2.hkl |
CCDC reference: 287677
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.088
- wR factor = 0.307
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for S1 - C5 .. 22.02 su PLAT230_ALERT_2_B Hirshfeld Test Diff for S2 - C6 .. 19.68 su
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.307 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.79 mm PLAT084_ALERT_2_C High R2 Value .................................. 0.31 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C5 - C6 ... 1.43 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C10 H10 N4 S2
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was prepared according to the reported procedure (Zheng et al., 2003). Colorless single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a chloroform solution at room temperature.
All H atoms were positioned geometrically with Csp2—H = 0.93 Å and Csp3—H = 0.97 Å; they were constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). The short C5—C6 distance of 1.425 (7) Å may be an artifact of the large atomic displacements.
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure (Rigaku, 2004).
Fig. 1. ORTEPII (Johnson, 1976) view of (I), showing atomic displacement ellipsoids at the 30% probability level. |
C10H10N4S2 | F(000) = 520 |
Mr = 250.34 | Dx = 1.424 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11354 reflections |
a = 8.0524 (16) Å | θ = 3.0–27.5° |
b = 19.884 (4) Å | µ = 0.43 mm−1 |
c = 8.1541 (16) Å | T = 293 K |
β = 116.57 (3)° | Needle, colorless |
V = 1167.7 (4) Å3 | 0.79 × 0.24 × 0.16 mm |
Z = 4 |
Rigaku X-AXIS RAPID IP area-detector diffractometer | 2663 independent reflections |
Radiation source: rotating anode | 1706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.725, Tmax = 0.936 | k = −25→25 |
11145 measured reflections | l = −9→10 |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.307 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.2005P)2 + 0.4011P] where P = (Fo2 + 2Fc2)/3 |
2663 reflections | (Δ/σ)max = 0.046 |
145 parameters | Δρmax = 1.17 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
C10H10N4S2 | V = 1167.7 (4) Å3 |
Mr = 250.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.0524 (16) Å | µ = 0.43 mm−1 |
b = 19.884 (4) Å | T = 293 K |
c = 8.1541 (16) Å | 0.79 × 0.24 × 0.16 mm |
β = 116.57 (3)° |
Rigaku X-AXIS RAPID IP area-detector diffractometer | 2663 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1706 reflections with I > 2σ(I) |
Tmin = 0.725, Tmax = 0.936 | Rint = 0.080 |
11145 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | 0 restraints |
wR(F2) = 0.307 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.17 e Å−3 |
2663 reflections | Δρmin = −0.94 e Å−3 |
145 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.18017 (17) | −0.26723 (5) | −0.1152 (2) | 0.0743 (5) | |
S2 | −0.23919 (15) | −0.48544 (6) | −0.2296 (2) | 0.0793 (6) | |
N1 | 0.0708 (5) | −0.18705 (15) | −0.1171 (5) | 0.0537 (8) | |
N2 | 0.1370 (5) | −0.30332 (15) | −0.1231 (5) | 0.0604 (9) | |
N3 | −0.5083 (5) | −0.56394 (14) | −0.2632 (5) | 0.0552 (8) | |
N4 | −0.5653 (5) | −0.44748 (16) | −0.2418 (6) | 0.0643 (10) | |
C1 | 0.2316 (6) | −0.1727 (2) | −0.1195 (6) | 0.0614 (11) | |
H1B | 0.2645 | −0.1278 | −0.1180 | 0.074* | |
C2 | 0.3493 (6) | −0.2208 (2) | −0.1242 (7) | 0.0672 (12) | |
H2B | 0.4601 | −0.2097 | −0.1271 | 0.081* | |
C3 | 0.2971 (6) | −0.2861 (2) | −0.1245 (7) | 0.0685 (12) | |
H3B | 0.3760 | −0.3201 | −0.1256 | 0.082* | |
C4 | 0.0330 (5) | −0.25188 (18) | −0.1194 (5) | 0.0483 (8) | |
C5 | −0.1764 (7) | −0.3603 (3) | −0.0842 (6) | 0.0880 (17) | |
H5A | −0.0516 | −0.3755 | −0.0041 | 0.106* | |
H5B | −0.2578 | −0.3732 | −0.0307 | 0.106* | |
C6 | −0.2392 (6) | −0.3889 (3) | −0.2624 (6) | 0.0807 (16) | |
H6A | −0.1566 | −0.3767 | −0.3150 | 0.097* | |
H6B | −0.3632 | −0.3731 | −0.3431 | 0.097* | |
C7 | −0.4615 (5) | −0.49969 (17) | −0.2463 (5) | 0.0487 (9) | |
C8 | −0.7334 (6) | −0.4635 (2) | −0.2590 (7) | 0.0694 (12) | |
H8A | −0.8103 | −0.4292 | −0.2556 | 0.083* | |
C9 | −0.7973 (6) | −0.5280 (2) | −0.2812 (6) | 0.0597 (10) | |
H9A | −0.9161 | −0.5380 | −0.2964 | 0.072* | |
C10 | −0.6780 (6) | −0.57709 (19) | −0.2802 (5) | 0.0560 (10) | |
H10A | −0.7167 | −0.6217 | −0.2917 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0622 (8) | 0.0436 (7) | 0.1421 (12) | 0.0004 (4) | 0.0681 (8) | 0.0002 (6) |
S2 | 0.0473 (7) | 0.0519 (8) | 0.1518 (13) | −0.0085 (4) | 0.0562 (7) | −0.0281 (7) |
N1 | 0.0515 (18) | 0.0385 (16) | 0.0745 (19) | −0.0002 (13) | 0.0312 (15) | 0.0022 (13) |
N2 | 0.0462 (17) | 0.0333 (16) | 0.105 (2) | −0.0013 (12) | 0.0373 (17) | −0.0053 (16) |
N3 | 0.0564 (19) | 0.0373 (16) | 0.078 (2) | −0.0019 (13) | 0.0353 (16) | −0.0062 (14) |
N4 | 0.0490 (18) | 0.0357 (16) | 0.119 (3) | −0.0031 (13) | 0.0475 (19) | −0.0113 (17) |
C1 | 0.054 (2) | 0.044 (2) | 0.087 (3) | −0.0127 (16) | 0.032 (2) | −0.0031 (18) |
C2 | 0.047 (2) | 0.066 (3) | 0.093 (3) | −0.0176 (19) | 0.036 (2) | −0.015 (2) |
C3 | 0.048 (2) | 0.050 (2) | 0.113 (3) | −0.0006 (17) | 0.040 (2) | −0.017 (2) |
C4 | 0.0403 (16) | 0.0369 (17) | 0.070 (2) | −0.0017 (13) | 0.0270 (16) | 0.0022 (14) |
C5 | 0.063 (3) | 0.133 (5) | 0.072 (3) | −0.022 (3) | 0.034 (2) | 0.004 (3) |
C6 | 0.047 (2) | 0.128 (5) | 0.070 (2) | −0.013 (3) | 0.029 (2) | 0.010 (3) |
C7 | 0.0397 (18) | 0.0359 (17) | 0.074 (2) | −0.0044 (13) | 0.0283 (16) | −0.0107 (15) |
C8 | 0.051 (2) | 0.050 (2) | 0.121 (4) | 0.0003 (17) | 0.051 (2) | −0.008 (2) |
C9 | 0.047 (2) | 0.060 (2) | 0.082 (3) | −0.0116 (18) | 0.0374 (19) | −0.0066 (19) |
C10 | 0.063 (2) | 0.0391 (18) | 0.074 (2) | −0.0136 (16) | 0.038 (2) | −0.0070 (16) |
S1—C4 | 1.759 (4) | C2—C3 | 1.366 (6) |
S1—C5 | 1.866 (7) | C2—H2B | 0.9300 |
S2—C7 | 1.757 (4) | C3—H3B | 0.9300 |
S2—C6 | 1.939 (6) | C5—C6 | 1.425 (7) |
N1—C4 | 1.323 (5) | C5—H5A | 0.9700 |
N1—C1 | 1.334 (5) | C5—H5B | 0.9700 |
N2—C4 | 1.331 (5) | C6—H6A | 0.9700 |
N2—C3 | 1.338 (5) | C6—H6B | 0.9700 |
N3—C7 | 1.322 (4) | C8—C9 | 1.362 (6) |
N3—C10 | 1.337 (5) | C8—H8A | 0.9300 |
N4—C8 | 1.336 (5) | C9—C10 | 1.367 (6) |
N4—C7 | 1.344 (5) | C9—H9A | 0.9300 |
C1—C2 | 1.358 (6) | C10—H10A | 0.9300 |
C1—H1B | 0.9300 | ||
C4—S1—C5 | 102.6 (2) | C6—C5—H5B | 110.5 |
C7—S2—C6 | 102.24 (19) | S1—C5—H5B | 110.5 |
C4—N1—C1 | 115.2 (3) | H5A—C5—H5B | 108.7 |
C4—N2—C3 | 115.0 (3) | C5—C6—S2 | 106.0 (4) |
C7—N3—C10 | 115.5 (3) | C5—C6—H6A | 110.5 |
C8—N4—C7 | 115.2 (3) | S2—C6—H6A | 110.5 |
N1—C1—C2 | 123.0 (4) | C5—C6—H6B | 110.5 |
N1—C1—H1B | 118.5 | S2—C6—H6B | 110.5 |
C2—C1—H1B | 118.5 | H6A—C6—H6B | 108.7 |
C1—C2—C3 | 116.8 (4) | N3—C7—N4 | 126.7 (3) |
C1—C2—H2B | 121.6 | N3—C7—S2 | 113.4 (3) |
C3—C2—H2B | 121.6 | N4—C7—S2 | 119.9 (3) |
N2—C3—C2 | 122.7 (4) | N4—C8—C9 | 122.9 (4) |
N2—C3—H3B | 118.7 | N4—C8—H8A | 118.6 |
C2—C3—H3B | 118.7 | C9—C8—H8A | 118.6 |
N1—C4—N2 | 127.3 (4) | C8—C9—C10 | 116.7 (4) |
N1—C4—S1 | 112.9 (3) | C8—C9—H9A | 121.7 |
N2—C4—S1 | 119.8 (3) | C10—C9—H9A | 121.7 |
C6—C5—S1 | 106.3 (4) | N3—C10—C9 | 122.9 (3) |
C6—C5—H5A | 110.5 | N3—C10—H10A | 118.5 |
S1—C5—H5A | 110.5 | C9—C10—H10A | 118.5 |
C4—N1—C1—C2 | 0.1 (6) | C7—S2—C6—C5 | 88.1 (4) |
N1—C1—C2—C3 | −0.7 (7) | C10—N3—C7—N4 | 1.1 (6) |
C4—N2—C3—C2 | −0.8 (7) | C10—N3—C7—S2 | −178.7 (3) |
C1—C2—C3—N2 | 1.0 (7) | C8—N4—C7—N3 | −1.0 (7) |
C1—N1—C4—N2 | 0.3 (6) | C8—N4—C7—S2 | 178.8 (3) |
C1—N1—C4—S1 | 179.8 (3) | C6—S2—C7—N3 | 167.7 (3) |
C3—N2—C4—N1 | 0.1 (7) | C6—S2—C7—N4 | −12.1 (4) |
C3—N2—C4—S1 | −179.4 (3) | C7—N4—C8—C9 | −0.6 (7) |
C5—S1—C4—N1 | −171.9 (3) | N4—C8—C9—C10 | 1.8 (7) |
C5—S1—C4—N2 | 7.7 (4) | C7—N3—C10—C9 | 0.4 (6) |
C4—S1—C5—C6 | −83.4 (4) | C8—C9—C10—N3 | −1.7 (7) |
S1—C5—C6—S2 | −179.0 (2) |
Experimental details
Crystal data | |
Chemical formula | C10H10N4S2 |
Mr | 250.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.0524 (16), 19.884 (4), 8.1541 (16) |
β (°) | 116.57 (3) |
V (Å3) | 1167.7 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.79 × 0.24 × 0.16 |
Data collection | |
Diffractometer | Rigaku X-AXIS RAPID IP area-detector diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.725, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11145, 2663, 1706 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.088, 0.307, 1.02 |
No. of reflections | 2663 |
No. of parameters | 145 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.17, −0.94 |
Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), CrystalStructure (Rigaku, 2004).
S1—C4 | 1.759 (4) | S2—C7 | 1.757 (4) |
S1—C5 | 1.866 (7) | S2—C6 | 1.939 (6) |
C4—S1—C5 | 102.6 (2) | C7—S2—C6 | 102.24 (19) |
C5—S1—C4—N2 | 7.7 (4) | C7—S2—C6—C5 | 88.1 (4) |
C4—S1—C5—C6 | −83.4 (4) | C6—S2—C7—N4 | −12.1 (4) |
S1—C5—C6—S2 | −179.0 (2) |
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A large number of complexes of dithioether ligands containing N-heterocyclic groups have been synthesized and investigated, because of their diverse coordination capabilities and the important properties of their metal complexes (Zheng et al., 2003; Hong et al., 2000). However, crystallographic studies of only a few ligands have been reported. In the present paper, we report the crystal structure of the title compound, (I).
As shown in Fig. 1, the molecule adopts an anti conformation (Goodgame et al., 1999) with a pseudo-torsion angle C4—S1···S2—C7 of −174.9 (2)°. The pyrimidine rings (N1/C1–C3/N2/C4 and N3/C7/N4/C8–C10), with a dihedral angle of 6.8 (2)° to each other, incline to the spacer unit plane (S1—C5—C6—S2) at angles of 81.8 (4) and 86.9 (4)°, respectively. The S1···S2 non-bonding distance is 4.419 (2) Å. The bond dimensions are within the range reported in a similar compound, 2,4,6-trimethyl-1,3,5-tris(2-pyrimidinylthiomethyl)benzene (Zheng et al., 2002). Both the S—Csp2 and the S—Csp3 bond distances of (I) show little deviation in comparison with those of the analogous compound 1,2-bis(phenylthio)ethane (Hou et al., 2005), despite various substituted groups. The molecule of (I) does not possess any crystallographic symmetry, being different from the inversion symmetry of several reported alkyl dithioether compounds (Chen et al., 2005; Hou et al., 2005).
In the crystal of the binuclear silver(I) nitrate complex with (I) as a chelating and bridging ligand (Zheng et al., 2003), the thioether adopts a gauche conformation with an S···S non-bonding distance of 3.44 (3) Å.