2,3-Bis(1-methyl-1H-imidazol-2-ylsulfanyl­methyl)­quinoxaline

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.

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

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Computing details

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

Crystal data

C18H18N6S2	Z = 2
Mr = 382.50	F(000) = 400
Triclinic, P1	Dx = 1.383 Mg m^−3
Hall symbol: -P 1	Melting point: 374 K
a = 6.8978 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.953 (2) Å	Cell parameters from 1798 reflections
c = 14.556 (3) Å	θ = 2.9–26.1°
α = 96.495 (4)°	µ = 0.31 mm^−1
β = 97.418 (3)°	T = 294 K
γ = 109.863 (3)°	Block, yellow
V = 918.7 (3) Å^3	0.28 × 0.24 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3244 independent reflections
Radiation source: fine-focus sealed tube	2350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
Tmin = 0.923, Tmax = 0.958	k = −9→11
4713 measured reflections	l = −17→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.067P)^2 + 0.146P] where P = (Fo^2 + 2Fc^2)/3
3244 reflections	(Δ/σ)max = 0.002
237 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.24 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
S1	1.35146 (10)	0.12202 (7)	0.46720 (5)	0.0503 (2)
S2	0.77718 (12)	0.23331 (7)	0.27469 (5)	0.0572 (2)
N1	1.1229 (3)	−0.0871 (2)	0.30655 (14)	0.0425 (5)
N2	0.7135 (3)	−0.1509 (2)	0.20914 (14)	0.0429 (5)
N3	1.6020 (3)	0.3723 (2)	0.58181 (14)	0.0464 (5)
N4	1.2665 (3)	0.3184 (2)	0.58856 (16)	0.0566 (6)
N5	0.5893 (3)	0.1870 (2)	0.09107 (15)	0.0467 (5)
N6	0.9146 (3)	0.1882 (2)	0.11143 (18)	0.0586 (6)
C1	1.0296 (4)	−0.2055 (2)	0.23596 (17)	0.0409 (6)
C2	1.1400 (4)	−0.2976 (3)	0.21369 (19)	0.0507 (7)
H2	1.2760	−0.2766	0.2449	0.061*
C3	1.0458 (5)	−0.4172 (3)	0.1463 (2)	0.0595 (8)
H3	1.1178	−0.4785	0.1320	0.071*
C4	0.8436 (5)	−0.4492 (3)	0.0984 (2)	0.0614 (8)
H4	0.7824	−0.5313	0.0523	0.074*
C5	0.7332 (5)	−0.3616 (3)	0.11812 (19)	0.0558 (7)
H5	0.5981	−0.3838	0.0855	0.067*
C6	0.8260 (4)	−0.2377 (3)	0.18814 (17)	0.0419 (6)
C7	1.0119 (4)	−0.0083 (2)	0.32687 (16)	0.0386 (5)
C8	0.8033 (3)	−0.0407 (2)	0.27681 (16)	0.0375 (5)
C9	1.1045 (4)	0.1174 (3)	0.40570 (19)	0.0535 (7)
H9A	1.0078	0.1105	0.4493	0.064*
H9B	1.1253	0.2068	0.3809	0.064*
C10	1.4038 (4)	0.2785 (3)	0.54957 (16)	0.0410 (6)
C11	1.3839 (5)	0.4449 (3)	0.6483 (2)	0.0597 (8)
H11	1.3291	0.4997	0.6858	0.072*
C12	1.5877 (5)	0.4794 (3)	0.64540 (19)	0.0572 (7)
H12	1.6976	0.5599	0.6797	0.069*
C13	1.7926 (4)	0.3652 (4)	0.5518 (2)	0.0762 (10)
H13A	1.8091	0.2764	0.5639	0.114*
H13B	1.9112	0.4459	0.5861	0.114*
H13C	1.7829	0.3684	0.4858	0.114*
C14	0.6765 (4)	0.0502 (3)	0.30156 (18)	0.0472 (6)
H14A	0.6722	0.0564	0.3682	0.057*
H14B	0.5339	0.0019	0.2677	0.057*
C15	0.7616 (4)	0.1992 (2)	0.15380 (18)	0.0443 (6)
C16	0.8366 (5)	0.1697 (3)	0.0183 (2)	0.0657 (8)
H16	0.9105	0.1596	−0.0295	0.079*
C17	0.6391 (5)	0.1680 (3)	0.00393 (19)	0.0574 (7)
H17	0.5538	0.1563	−0.0536	0.069*
C18	0.3942 (4)	0.1972 (3)	0.1122 (2)	0.0713 (9)
H18A	0.3528	0.1436	0.1617	0.107*
H18B	0.2872	0.1576	0.0571	0.107*
H18C	0.4135	0.2969	0.1318	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0429 (4)	0.0548 (4)	0.0532 (4)	0.0259 (3)	−0.0003 (3)	−0.0073 (3)
S2	0.0755 (5)	0.0471 (4)	0.0524 (4)	0.0343 (4)	−0.0027 (4)	−0.0002 (3)
N1	0.0395 (11)	0.0399 (12)	0.0480 (12)	0.0158 (10)	0.0058 (9)	0.0041 (10)
N2	0.0414 (11)	0.0425 (12)	0.0429 (12)	0.0138 (10)	0.0057 (9)	0.0060 (10)
N3	0.0391 (12)	0.0513 (13)	0.0440 (12)	0.0122 (10)	0.0043 (9)	0.0053 (10)
N4	0.0461 (13)	0.0598 (15)	0.0637 (15)	0.0228 (11)	0.0125 (11)	−0.0051 (12)
N5	0.0419 (12)	0.0446 (12)	0.0548 (14)	0.0193 (10)	0.0024 (10)	0.0088 (10)
N6	0.0465 (13)	0.0588 (15)	0.0750 (17)	0.0221 (11)	0.0165 (12)	0.0125 (12)
C1	0.0467 (14)	0.0352 (13)	0.0425 (14)	0.0149 (11)	0.0125 (11)	0.0076 (11)
C2	0.0573 (16)	0.0455 (15)	0.0556 (16)	0.0245 (13)	0.0156 (13)	0.0084 (13)
C3	0.078 (2)	0.0469 (16)	0.0613 (18)	0.0285 (15)	0.0249 (16)	0.0077 (14)
C4	0.087 (2)	0.0358 (15)	0.0540 (17)	0.0140 (15)	0.0154 (16)	−0.0011 (12)
C5	0.0606 (17)	0.0463 (16)	0.0493 (16)	0.0092 (14)	0.0030 (13)	0.0026 (13)
C6	0.0473 (14)	0.0367 (13)	0.0398 (13)	0.0114 (12)	0.0102 (11)	0.0079 (11)
C7	0.0399 (13)	0.0368 (13)	0.0407 (13)	0.0159 (11)	0.0072 (11)	0.0064 (10)
C8	0.0378 (13)	0.0387 (13)	0.0384 (13)	0.0143 (11)	0.0085 (10)	0.0115 (11)
C9	0.0491 (15)	0.0512 (16)	0.0590 (17)	0.0264 (13)	−0.0053 (13)	−0.0058 (13)
C10	0.0368 (13)	0.0458 (14)	0.0401 (13)	0.0163 (12)	0.0051 (11)	0.0040 (11)
C11	0.071 (2)	0.0530 (18)	0.0574 (18)	0.0322 (16)	0.0049 (15)	−0.0064 (14)
C12	0.0648 (19)	0.0414 (15)	0.0543 (17)	0.0127 (14)	−0.0021 (14)	−0.0018 (13)
C13	0.0392 (16)	0.107 (3)	0.069 (2)	0.0131 (17)	0.0132 (14)	−0.0014 (19)
C14	0.0451 (14)	0.0559 (16)	0.0476 (15)	0.0266 (13)	0.0089 (12)	0.0093 (12)
C15	0.0430 (14)	0.0370 (14)	0.0555 (16)	0.0180 (12)	0.0061 (12)	0.0097 (11)
C16	0.073 (2)	0.064 (2)	0.068 (2)	0.0260 (17)	0.0308 (17)	0.0183 (16)
C17	0.072 (2)	0.0489 (16)	0.0469 (16)	0.0183 (15)	0.0034 (14)	0.0103 (13)
C18	0.0486 (17)	0.081 (2)	0.088 (2)	0.0333 (16)	0.0022 (16)	0.0066 (18)

Geometric parameters (Å, º)

S1—C9	1.803 (3)	C4—C5	1.369 (4)
S1—C10	1.754 (2)	C4—H4	0.9300
S2—C14	1.825 (3)	C5—C6	1.408 (3)
S2—C15	1.736 (3)	C5—H5	0.9300
N1—C7	1.305 (3)	C7—C8	1.437 (3)
N1—C1	1.378 (3)	C7—C9	1.494 (3)
N2—C8	1.301 (3)	C8—C14	1.503 (3)
N2—C6	1.378 (3)	C9—H9A	0.9700
N3—C10	1.352 (3)	C9—H9B	0.9700
N3—C12	1.369 (3)	C11—C12	1.336 (4)
N3—C13	1.459 (3)	C11—H11	0.9300
N4—C10	1.311 (3)	C12—H12	0.9300
N4—C11	1.369 (3)	C13—H13A	0.9600
N5—C15	1.362 (3)	C13—H13B	0.9600
N5—C17	1.365 (3)	C13—H13C	0.9600
N5—C18	1.452 (3)	C14—H14A	0.9700
N6—C15	1.319 (3)	C14—H14B	0.9700
N6—C16	1.360 (4)	C16—C17	1.345 (4)
C1—C6	1.396 (3)	C16—H16	0.9300
C1—C2	1.413 (3)	C17—H17	0.9300
C2—C3	1.359 (4)	C18—H18A	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C3—C4	1.389 (4)	C18—H18C	0.9600
C3—H3	0.9300
C10—S1—C9	96.95 (11)	C7—C9—H9B	109.4
C15—S2—C14	101.70 (11)	S1—C9—H9B	109.4
C7—N1—C1	117.0 (2)	H9A—C9—H9B	108.0
C8—N2—C6	117.0 (2)	S1—C10—N3	121.20 (18)
C10—N3—C12	106.3 (2)	S1—C10—N4	126.74 (19)
C10—N3—C13	127.1 (2)	N3—C10—N4	112.0 (2)
C12—N3—C13	126.6 (2)	C12—C11—N4	111.0 (2)
C10—N4—C11	104.5 (2)	C12—C11—H11	124.5
C15—N5—C17	106.2 (2)	N4—C11—H11	124.5
C15—N5—C18	127.1 (2)	C11—C12—N3	106.1 (2)
C17—N5—C18	126.6 (2)	C11—C12—H12	126.9
C15—N6—C16	104.4 (2)	N3—C12—H12	126.9
N1—C1—C6	120.9 (2)	N3—C13—H13A	109.5
N1—C1—C2	119.3 (2)	N3—C13—H13B	109.5
C6—C1—C2	119.7 (2)	H13A—C13—H13B	109.5
C3—C2—C1	119.5 (3)	N3—C13—H13C	109.5
C3—C2—H2	120.3	H13A—C13—H13C	109.5
C1—C2—H2	120.3	H13B—C13—H13C	109.5
C2—C3—C4	120.9 (3)	C8—C14—S2	114.05 (17)
C2—C3—H3	119.5	C8—C14—H14A	108.7
C4—C3—H3	119.5	S2—C14—H14A	108.7
C5—C4—C3	120.9 (3)	C8—C14—H14B	108.7
C5—C4—H4	119.5	S2—C14—H14B	108.7
C3—C4—H4	119.5	H14A—C14—H14B	107.6
C4—C5—C6	119.4 (3)	S2—C15—N5	123.13 (19)
C4—C5—H5	120.3	S2—C15—N6	125.0 (2)
C6—C5—H5	120.3	N5—C15—N6	111.8 (2)
N2—C6—C1	121.1 (2)	C17—C16—N6	111.6 (3)
N2—C6—C5	119.4 (2)	C17—C16—H16	124.2
C1—C6—C5	119.5 (2)	N6—C16—H16	124.2
N1—C7—C8	121.9 (2)	C16—C17—N5	106.0 (3)
N1—C7—C9	118.6 (2)	C16—C17—H17	127.0
C8—C7—C9	119.5 (2)	N5—C17—H17	127.0
N2—C8—C7	122.0 (2)	N5—C18—H18A	109.5
N2—C8—C14	116.6 (2)	N5—C18—H18B	109.5
C7—C8—C14	121.3 (2)	H18A—C18—H18B	109.5
C7—C9—S1	111.30 (17)	N5—C18—H18C	109.5
C7—C9—H9A	109.4	H18A—C18—H18C	109.5
S1—C9—H9A	109.4	H18B—C18—H18C	109.5
C7—N1—C1—C6	0.7 (3)	C11—N4—C10—S1	179.0 (2)
C7—N1—C1—C2	−177.6 (2)	C12—N3—C10—N4	−0.4 (3)
N1—C1—C2—C3	177.8 (2)	C13—N3—C10—N4	−177.7 (3)
C6—C1—C2—C3	−0.5 (4)	C12—N3—C10—S1	−178.94 (18)
C1—C2—C3—C4	0.7 (4)	C13—N3—C10—S1	3.8 (4)
C2—C3—C4—C5	−0.4 (4)	C9—S1—C10—N4	35.5 (3)
C3—C4—C5—C6	−0.2 (4)	C9—S1—C10—N3	−146.2 (2)
C8—N2—C6—C1	−1.7 (3)	C10—N4—C11—C12	−0.4 (3)
C8—N2—C6—C5	177.5 (2)	N4—C11—C12—N3	0.2 (3)
N1—C1—C6—N2	0.9 (4)	C10—N3—C12—C11	0.1 (3)
C2—C1—C6—N2	179.2 (2)	C13—N3—C12—C11	177.4 (3)
N1—C1—C6—C5	−178.3 (2)	N2—C8—C14—S2	−113.0 (2)
C2—C1—C6—C5	0.0 (4)	C7—C8—C14—S2	68.1 (3)
C4—C5—C6—N2	−178.9 (2)	C15—S2—C14—C8	61.0 (2)
C4—C5—C6—C1	0.4 (4)	C16—N6—C15—N5	0.6 (3)
C1—N1—C7—C8	−1.4 (3)	C16—N6—C15—S2	−176.7 (2)
C1—N1—C7—C9	177.5 (2)	C17—N5—C15—N6	−0.4 (3)
C6—N2—C8—C7	1.0 (3)	C18—N5—C15—N6	−178.4 (2)
C6—N2—C8—C14	−177.9 (2)	C17—N5—C15—S2	176.96 (18)
N1—C7—C8—N2	0.6 (4)	C18—N5—C15—S2	−1.1 (4)
C9—C7—C8—N2	−178.3 (2)	C14—S2—C15—N6	−92.9 (2)
N1—C7—C8—C14	179.4 (2)	C14—S2—C15—N5	90.1 (2)
C9—C7—C8—C14	0.5 (3)	C15—N6—C16—C17	−0.6 (3)
N1—C7—C9—S1	−6.5 (3)	N6—C16—C17—N5	0.4 (3)
C8—C7—C9—S1	172.42 (18)	C15—N5—C17—C16	0.0 (3)
C10—S1—C9—C7	179.8 (2)	C18—N5—C17—C16	178.1 (3)
C11—N4—C10—N3	0.5 (3)