Bis­[trans-2-(2-phenyl­ethenyl)­pyrazin-4-ium] tetra­chloro­zincate

The title compound, (C₁₂H₁₁N₂)₂[ZnCl₄], was prepared from Zn(OAc)₂·2H₂O and trans-2-(2-phenyl­ethenyl)­pyrazine in hydro­chloric acid. The two trans-2-(2-phenyl­ethenyl)­pyrazin-4-ium cations combine with one ZnCl₄²⁻ anion through N—H...Cl hydrogen bonds and C—H...Cl interactions. The Zn²⁺ species is situated on a twofold symmetry axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.074
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        Zn1

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

   1 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
   0 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: 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.

Bis[trans-2-(2-phenylethenyl)pyrazin-4-ium)] tetrachlorozincate

Crystal data

(C12H11N2)2[ZnCl4]	F(000) = 1168
Mr = 573.63	Dx = 1.515 Mg m^−3
Monoclinic, C2/c	Melting point: 455 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.806 (4) Å	Cell parameters from 739 reflections
b = 11.777 (4) Å	θ = 2.6–24.5°
c = 19.944 (7) Å	µ = 1.42 mm^−1
β = 97.660 (5)°	T = 293 K
V = 2515.5 (15) Å^3	Block, yellow
Z = 4	0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2576 independent reflections
Radiation source: fine-focus sealed tube	1850 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.755, Tmax = 0.797	k = −8→14
7101 measured reflections	l = −24→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.5088P] where P = (Fo^2 + 2Fc^2)/3
2576 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.22 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
Zn1	0.0000	0.82302 (4)	0.2500	0.04068 (14)
Cl1	0.14667 (7)	0.94370 (6)	0.30382 (3)	0.0569 (2)
Cl2	0.08350 (7)	0.71288 (6)	0.17641 (3)	0.0572 (2)
N1	0.22587 (19)	1.1181 (2)	0.04054 (11)	0.0518 (6)
N2	0.1891 (2)	1.0630 (2)	0.16753 (11)	0.0530 (6)
H2	0.1778	1.0451	0.2081	0.064*
C1	0.1816 (2)	1.0153 (2)	0.05363 (12)	0.0423 (6)
C2	0.1638 (2)	0.9871 (2)	0.11938 (13)	0.0499 (7)
H2A	0.1345	0.9155	0.1291	0.060*
C3	0.2312 (2)	1.1660 (3)	0.15625 (14)	0.0542 (7)
H3	0.2476	1.2189	0.1909	0.065*
C4	0.2494 (2)	1.1909 (2)	0.09089 (14)	0.0552 (7)
H4	0.2797	1.2623	0.0818	0.066*
C5	0.1550 (2)	0.9366 (2)	−0.00231 (13)	0.0478 (7)
H5	0.1760	0.9593	−0.0440	0.057*
C6	0.1034 (2)	0.8354 (2)	0.00086 (13)	0.0474 (7)
H6	0.0828	0.8144	0.0429	0.057*
C7	0.0748 (2)	0.7525 (2)	−0.05325 (12)	0.0431 (6)
C8	0.0067 (3)	0.6565 (2)	−0.04155 (14)	0.0548 (7)
H8	−0.0195	0.6465	0.0006	0.066*
C9	−0.0231 (3)	0.5762 (2)	−0.09046 (15)	0.0608 (8)
H9	−0.0698	0.5129	−0.0816	0.073*
C10	0.0160 (3)	0.5891 (3)	−0.15273 (15)	0.0636 (8)
H10	−0.0040	0.5347	−0.1862	0.076*
C11	0.0846 (3)	0.6827 (3)	−0.16507 (14)	0.0658 (8)
H11	0.1116	0.6913	−0.2071	0.079*
C12	0.1141 (2)	0.7637 (2)	−0.11631 (14)	0.0530 (7)
H12	0.1608	0.8268	−0.1256	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0487 (3)	0.0353 (2)	0.0389 (2)	0.000	0.00868 (18)	0.000
Cl1	0.0723 (5)	0.0482 (4)	0.0469 (4)	−0.0132 (3)	−0.0039 (3)	−0.0035 (3)
Cl2	0.0744 (5)	0.0456 (4)	0.0570 (4)	−0.0035 (3)	0.0285 (4)	−0.0111 (3)
N1	0.0563 (14)	0.0499 (15)	0.0486 (14)	−0.0098 (11)	0.0047 (11)	0.0056 (12)
N2	0.0623 (15)	0.0555 (15)	0.0411 (13)	−0.0042 (12)	0.0070 (10)	0.0038 (12)
C1	0.0367 (14)	0.0455 (16)	0.0439 (15)	0.0017 (12)	0.0030 (11)	0.0079 (13)
C2	0.0595 (17)	0.0422 (16)	0.0477 (16)	−0.0063 (13)	0.0060 (13)	0.0030 (14)
C3	0.0553 (17)	0.0502 (18)	0.0562 (18)	−0.0096 (14)	0.0040 (13)	−0.0065 (15)
C4	0.0580 (17)	0.0472 (17)	0.0599 (19)	−0.0151 (14)	0.0054 (14)	0.0045 (15)
C5	0.0503 (16)	0.0512 (18)	0.0426 (16)	0.0007 (14)	0.0089 (12)	0.0075 (14)
C6	0.0463 (15)	0.0542 (18)	0.0426 (15)	0.0014 (14)	0.0090 (12)	0.0059 (14)
C7	0.0398 (14)	0.0460 (16)	0.0430 (15)	0.0031 (12)	0.0029 (11)	0.0037 (13)
C8	0.0580 (17)	0.0545 (19)	0.0531 (17)	−0.0044 (15)	0.0116 (13)	0.0095 (15)
C9	0.0630 (19)	0.0477 (18)	0.071 (2)	−0.0114 (15)	0.0056 (16)	0.0055 (17)
C10	0.070 (2)	0.0562 (19)	0.062 (2)	−0.0056 (16)	0.0001 (16)	−0.0069 (16)
C11	0.081 (2)	0.071 (2)	0.0469 (18)	−0.0131 (18)	0.0150 (15)	−0.0055 (17)
C12	0.0548 (17)	0.0511 (17)	0.0541 (18)	−0.0099 (14)	0.0109 (14)	0.0029 (15)

Geometric parameters (Å, º)

Zn1—Cl2	2.2368 (8)	C5—C6	1.320 (3)
Zn1—Cl2^i	2.2369 (8)	C5—H5	0.9300
Zn1—Cl1^i	2.2871 (9)	C6—C7	1.458 (4)
Zn1—Cl1	2.2871 (9)	C6—H6	0.9300
N1—C4	1.319 (3)	C7—C12	1.386 (3)
N1—C1	1.340 (3)	C7—C8	1.386 (3)
N2—C2	1.314 (3)	C8—C9	1.366 (4)
N2—C3	1.325 (3)	C8—H8	0.9300
N2—H2	0.8600	C9—C10	1.372 (4)
C1—C2	1.391 (3)	C9—H9	0.9300
C1—C5	1.450 (4)	C10—C11	1.369 (4)
C2—H2A	0.9300	C10—H10	0.9300
C3—C4	1.376 (4)	C11—C12	1.369 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—H4	0.9300	C12—H12	0.9300
Cl2—Zn1—Cl2^i	109.12 (5)	C6—C5—H5	117.2
Cl2—Zn1—Cl1^i	111.55 (3)	C1—C5—H5	117.2
Cl2^i—Zn1—Cl1^i	110.70 (3)	C5—C6—C7	128.2 (3)
Cl2—Zn1—Cl1	110.70 (3)	C5—C6—H6	115.9
Cl2^i—Zn1—Cl1	111.55 (3)	C7—C6—H6	115.9
Cl1^i—Zn1—Cl1	103.15 (5)	C12—C7—C8	117.6 (3)
C4—N1—C1	118.5 (2)	C12—C7—C6	123.2 (2)
C2—N2—C3	122.8 (2)	C8—C7—C6	119.1 (2)
C2—N2—H2	118.6	C9—C8—C7	121.6 (3)
C3—N2—H2	118.6	C9—C8—H8	119.2
N1—C1—C2	119.9 (2)	C7—C8—H8	119.2
N1—C1—C5	117.9 (2)	C8—C9—C10	119.9 (3)
C2—C1—C5	122.3 (2)	C8—C9—H9	120.1
N2—C2—C1	119.0 (3)	C10—C9—H9	120.1
N2—C2—H2A	120.5	C11—C10—C9	119.4 (3)
C1—C2—H2A	120.5	C11—C10—H10	120.3
N2—C3—C4	116.8 (3)	C9—C10—H10	120.3
N2—C3—H3	121.6	C10—C11—C12	120.9 (3)
C4—C3—H3	121.6	C10—C11—H11	119.5
N1—C4—C3	123.1 (3)	C12—C11—H11	119.5
N1—C4—H4	118.5	C11—C12—C7	120.5 (3)
C3—C4—H4	118.5	C11—C12—H12	119.7
C6—C5—C1	125.6 (2)	C7—C12—H12	119.7
C4—N1—C1—C2	−1.2 (4)	C5—C6—C7—C12	8.7 (4)
C4—N1—C1—C5	179.4 (2)	C5—C6—C7—C8	−172.2 (3)
C3—N2—C2—C1	−0.1 (4)	C12—C7—C8—C9	−1.1 (4)
N1—C1—C2—N2	1.1 (4)	C6—C7—C8—C9	179.8 (3)
C5—C1—C2—N2	−179.5 (2)	C7—C8—C9—C10	0.7 (4)
C2—N2—C3—C4	−0.8 (4)	C8—C9—C10—C11	0.0 (4)
C1—N1—C4—C3	0.3 (4)	C9—C10—C11—C12	−0.4 (5)
N2—C3—C4—N1	0.6 (4)	C10—C11—C12—C7	0.0 (5)
N1—C1—C5—C6	−175.2 (2)	C8—C7—C12—C11	0.7 (4)
C2—C1—C5—C6	5.4 (4)	C6—C7—C12—C11	179.8 (3)
C1—C5—C6—C7	−179.7 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1	0.86	2.31	3.147 (2)	163
C2—H2A···Cl2	0.93	2.65	3.569 (2)	169