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The two terminal 1-methyl­imidazol-2-ylsulfanyl groups adopt a syn conformation with respect to the central quinoxaline ring system in the title compound, C18H18N6S2.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033404/tk6275sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033404/tk6275Isup2.hkl
Contains datablock I

CCDC reference: 289909

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.004 Å
  • R factor = 0.040
  • wR factor = 0.122
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

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

2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanylmethyl)quinoxaline top
Crystal data top
C18H18N6S2Z = 2
Mr = 382.50F(000) = 400
Triclinic, P1Dx = 1.383 Mg m3
Hall symbol: -P 1Melting point: 374 K
a = 6.8978 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.953 (2) ÅCell parameters from 1798 reflections
c = 14.556 (3) Åθ = 2.9–26.1°
α = 96.495 (4)°µ = 0.31 mm1
β = 97.418 (3)°T = 294 K
γ = 109.863 (3)°Block, yellow
V = 918.7 (3) Å30.28 × 0.24 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3244 independent reflections
Radiation source: fine-focus sealed tube2350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 78
Tmin = 0.923, Tmax = 0.958k = 911
4713 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.067P)2 + 0.146P]
where P = (Fo2 + 2Fc2)/3
3244 reflections(Δ/σ)max = 0.002
237 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S11.35146 (10)0.12202 (7)0.46720 (5)0.0503 (2)
S20.77718 (12)0.23331 (7)0.27469 (5)0.0572 (2)
N11.1229 (3)0.0871 (2)0.30655 (14)0.0425 (5)
N20.7135 (3)0.1509 (2)0.20914 (14)0.0429 (5)
N31.6020 (3)0.3723 (2)0.58181 (14)0.0464 (5)
N41.2665 (3)0.3184 (2)0.58856 (16)0.0566 (6)
N50.5893 (3)0.1870 (2)0.09107 (15)0.0467 (5)
N60.9146 (3)0.1882 (2)0.11143 (18)0.0586 (6)
C11.0296 (4)0.2055 (2)0.23596 (17)0.0409 (6)
C21.1400 (4)0.2976 (3)0.21369 (19)0.0507 (7)
H21.27600.27660.24490.061*
C31.0458 (5)0.4172 (3)0.1463 (2)0.0595 (8)
H31.11780.47850.13200.071*
C40.8436 (5)0.4492 (3)0.0984 (2)0.0614 (8)
H40.78240.53130.05230.074*
C50.7332 (5)0.3616 (3)0.11812 (19)0.0558 (7)
H50.59810.38380.08550.067*
C60.8260 (4)0.2377 (3)0.18814 (17)0.0419 (6)
C71.0119 (4)0.0083 (2)0.32687 (16)0.0386 (5)
C80.8033 (3)0.0407 (2)0.27681 (16)0.0375 (5)
C91.1045 (4)0.1174 (3)0.40570 (19)0.0535 (7)
H9A1.00780.11050.44930.064*
H9B1.12530.20680.38090.064*
C101.4038 (4)0.2785 (3)0.54957 (16)0.0410 (6)
C111.3839 (5)0.4449 (3)0.6483 (2)0.0597 (8)
H111.32910.49970.68580.072*
C121.5877 (5)0.4794 (3)0.64540 (19)0.0572 (7)
H121.69760.55990.67970.069*
C131.7926 (4)0.3652 (4)0.5518 (2)0.0762 (10)
H13A1.80910.27640.56390.114*
H13B1.91120.44590.58610.114*
H13C1.78290.36840.48580.114*
C140.6765 (4)0.0502 (3)0.30156 (18)0.0472 (6)
H14A0.67220.05640.36820.057*
H14B0.53390.00190.26770.057*
C150.7616 (4)0.1992 (2)0.15380 (18)0.0443 (6)
C160.8366 (5)0.1697 (3)0.0183 (2)0.0657 (8)
H160.91050.15960.02950.079*
C170.6391 (5)0.1680 (3)0.00393 (19)0.0574 (7)
H170.55380.15630.05360.069*
C180.3942 (4)0.1972 (3)0.1122 (2)0.0713 (9)
H18A0.35280.14360.16170.107*
H18B0.28720.15760.05710.107*
H18C0.41350.29690.13180.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0429 (4)0.0548 (4)0.0532 (4)0.0259 (3)0.0003 (3)0.0073 (3)
S20.0755 (5)0.0471 (4)0.0524 (4)0.0343 (4)0.0027 (4)0.0002 (3)
N10.0395 (11)0.0399 (12)0.0480 (12)0.0158 (10)0.0058 (9)0.0041 (10)
N20.0414 (11)0.0425 (12)0.0429 (12)0.0138 (10)0.0057 (9)0.0060 (10)
N30.0391 (12)0.0513 (13)0.0440 (12)0.0122 (10)0.0043 (9)0.0053 (10)
N40.0461 (13)0.0598 (15)0.0637 (15)0.0228 (11)0.0125 (11)0.0051 (12)
N50.0419 (12)0.0446 (12)0.0548 (14)0.0193 (10)0.0024 (10)0.0088 (10)
N60.0465 (13)0.0588 (15)0.0750 (17)0.0221 (11)0.0165 (12)0.0125 (12)
C10.0467 (14)0.0352 (13)0.0425 (14)0.0149 (11)0.0125 (11)0.0076 (11)
C20.0573 (16)0.0455 (15)0.0556 (16)0.0245 (13)0.0156 (13)0.0084 (13)
C30.078 (2)0.0469 (16)0.0613 (18)0.0285 (15)0.0249 (16)0.0077 (14)
C40.087 (2)0.0358 (15)0.0540 (17)0.0140 (15)0.0154 (16)0.0011 (12)
C50.0606 (17)0.0463 (16)0.0493 (16)0.0092 (14)0.0030 (13)0.0026 (13)
C60.0473 (14)0.0367 (13)0.0398 (13)0.0114 (12)0.0102 (11)0.0079 (11)
C70.0399 (13)0.0368 (13)0.0407 (13)0.0159 (11)0.0072 (11)0.0064 (10)
C80.0378 (13)0.0387 (13)0.0384 (13)0.0143 (11)0.0085 (10)0.0115 (11)
C90.0491 (15)0.0512 (16)0.0590 (17)0.0264 (13)0.0053 (13)0.0058 (13)
C100.0368 (13)0.0458 (14)0.0401 (13)0.0163 (12)0.0051 (11)0.0040 (11)
C110.071 (2)0.0530 (18)0.0574 (18)0.0322 (16)0.0049 (15)0.0064 (14)
C120.0648 (19)0.0414 (15)0.0543 (17)0.0127 (14)0.0021 (14)0.0018 (13)
C130.0392 (16)0.107 (3)0.069 (2)0.0131 (17)0.0132 (14)0.0014 (19)
C140.0451 (14)0.0559 (16)0.0476 (15)0.0266 (13)0.0089 (12)0.0093 (12)
C150.0430 (14)0.0370 (14)0.0555 (16)0.0180 (12)0.0061 (12)0.0097 (11)
C160.073 (2)0.064 (2)0.068 (2)0.0260 (17)0.0308 (17)0.0183 (16)
C170.072 (2)0.0489 (16)0.0469 (16)0.0183 (15)0.0034 (14)0.0103 (13)
C180.0486 (17)0.081 (2)0.088 (2)0.0333 (16)0.0022 (16)0.0066 (18)
Geometric parameters (Å, º) top
S1—C91.803 (3)C4—C51.369 (4)
S1—C101.754 (2)C4—H40.9300
S2—C141.825 (3)C5—C61.408 (3)
S2—C151.736 (3)C5—H50.9300
N1—C71.305 (3)C7—C81.437 (3)
N1—C11.378 (3)C7—C91.494 (3)
N2—C81.301 (3)C8—C141.503 (3)
N2—C61.378 (3)C9—H9A0.9700
N3—C101.352 (3)C9—H9B0.9700
N3—C121.369 (3)C11—C121.336 (4)
N3—C131.459 (3)C11—H110.9300
N4—C101.311 (3)C12—H120.9300
N4—C111.369 (3)C13—H13A0.9600
N5—C151.362 (3)C13—H13B0.9600
N5—C171.365 (3)C13—H13C0.9600
N5—C181.452 (3)C14—H14A0.9700
N6—C151.319 (3)C14—H14B0.9700
N6—C161.360 (4)C16—C171.345 (4)
C1—C61.396 (3)C16—H160.9300
C1—C21.413 (3)C17—H170.9300
C2—C31.359 (4)C18—H18A0.9600
C2—H20.9300C18—H18B0.9600
C3—C41.389 (4)C18—H18C0.9600
C3—H30.9300
C10—S1—C996.95 (11)C7—C9—H9B109.4
C15—S2—C14101.70 (11)S1—C9—H9B109.4
C7—N1—C1117.0 (2)H9A—C9—H9B108.0
C8—N2—C6117.0 (2)S1—C10—N3121.20 (18)
C10—N3—C12106.3 (2)S1—C10—N4126.74 (19)
C10—N3—C13127.1 (2)N3—C10—N4112.0 (2)
C12—N3—C13126.6 (2)C12—C11—N4111.0 (2)
C10—N4—C11104.5 (2)C12—C11—H11124.5
C15—N5—C17106.2 (2)N4—C11—H11124.5
C15—N5—C18127.1 (2)C11—C12—N3106.1 (2)
C17—N5—C18126.6 (2)C11—C12—H12126.9
C15—N6—C16104.4 (2)N3—C12—H12126.9
N1—C1—C6120.9 (2)N3—C13—H13A109.5
N1—C1—C2119.3 (2)N3—C13—H13B109.5
C6—C1—C2119.7 (2)H13A—C13—H13B109.5
C3—C2—C1119.5 (3)N3—C13—H13C109.5
C3—C2—H2120.3H13A—C13—H13C109.5
C1—C2—H2120.3H13B—C13—H13C109.5
C2—C3—C4120.9 (3)C8—C14—S2114.05 (17)
C2—C3—H3119.5C8—C14—H14A108.7
C4—C3—H3119.5S2—C14—H14A108.7
C5—C4—C3120.9 (3)C8—C14—H14B108.7
C5—C4—H4119.5S2—C14—H14B108.7
C3—C4—H4119.5H14A—C14—H14B107.6
C4—C5—C6119.4 (3)S2—C15—N5123.13 (19)
C4—C5—H5120.3S2—C15—N6125.0 (2)
C6—C5—H5120.3N5—C15—N6111.8 (2)
N2—C6—C1121.1 (2)C17—C16—N6111.6 (3)
N2—C6—C5119.4 (2)C17—C16—H16124.2
C1—C6—C5119.5 (2)N6—C16—H16124.2
N1—C7—C8121.9 (2)C16—C17—N5106.0 (3)
N1—C7—C9118.6 (2)C16—C17—H17127.0
C8—C7—C9119.5 (2)N5—C17—H17127.0
N2—C8—C7122.0 (2)N5—C18—H18A109.5
N2—C8—C14116.6 (2)N5—C18—H18B109.5
C7—C8—C14121.3 (2)H18A—C18—H18B109.5
C7—C9—S1111.30 (17)N5—C18—H18C109.5
C7—C9—H9A109.4H18A—C18—H18C109.5
S1—C9—H9A109.4H18B—C18—H18C109.5
C7—N1—C1—C60.7 (3)C11—N4—C10—S1179.0 (2)
C7—N1—C1—C2177.6 (2)C12—N3—C10—N40.4 (3)
N1—C1—C2—C3177.8 (2)C13—N3—C10—N4177.7 (3)
C6—C1—C2—C30.5 (4)C12—N3—C10—S1178.94 (18)
C1—C2—C3—C40.7 (4)C13—N3—C10—S13.8 (4)
C2—C3—C4—C50.4 (4)C9—S1—C10—N435.5 (3)
C3—C4—C5—C60.2 (4)C9—S1—C10—N3146.2 (2)
C8—N2—C6—C11.7 (3)C10—N4—C11—C120.4 (3)
C8—N2—C6—C5177.5 (2)N4—C11—C12—N30.2 (3)
N1—C1—C6—N20.9 (4)C10—N3—C12—C110.1 (3)
C2—C1—C6—N2179.2 (2)C13—N3—C12—C11177.4 (3)
N1—C1—C6—C5178.3 (2)N2—C8—C14—S2113.0 (2)
C2—C1—C6—C50.0 (4)C7—C8—C14—S268.1 (3)
C4—C5—C6—N2178.9 (2)C15—S2—C14—C861.0 (2)
C4—C5—C6—C10.4 (4)C16—N6—C15—N50.6 (3)
C1—N1—C7—C81.4 (3)C16—N6—C15—S2176.7 (2)
C1—N1—C7—C9177.5 (2)C17—N5—C15—N60.4 (3)
C6—N2—C8—C71.0 (3)C18—N5—C15—N6178.4 (2)
C6—N2—C8—C14177.9 (2)C17—N5—C15—S2176.96 (18)
N1—C7—C8—N20.6 (4)C18—N5—C15—S21.1 (4)
C9—C7—C8—N2178.3 (2)C14—S2—C15—N692.9 (2)
N1—C7—C8—C14179.4 (2)C14—S2—C15—N590.1 (2)
C9—C7—C8—C140.5 (3)C15—N6—C16—C170.6 (3)
N1—C7—C9—S16.5 (3)N6—C16—C17—N50.4 (3)
C8—C7—C9—S1172.42 (18)C15—N5—C17—C160.0 (3)
C10—S1—C9—C7179.8 (2)C18—N5—C17—C16178.1 (3)
C11—N4—C10—N30.5 (3)
 

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