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In the crystal structure of the title compound, [Zn(NCS)2(C6H8N2)2], the Zn atom and both iso­thio­cyanate groups lie on a crystallographic mirror plane. The Zn atom is in a distorted tetrahedral geometry. The crystal structure is stabilized by N—H...S hydrogen bonds and weak π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500810X/wn6335sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500810X/wn6335Isup2.hkl
Contains datablock I

CCDC reference: 270570

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.089
  • Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C7 .. 5.17 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N2 -ZN1 -N3 -C8 180.00 0.02 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N1 -ZN1 -N3 -C8 62.21 0.06 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 N1 -ZN1 -N3 -C8 -62.21 0.05 8.565 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 ZN1 -N2 -C7 -S1 0.00 0.01 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 27 ZN1 -N3 -C8 -S2 180.00 0.01 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 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 5 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 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Bis(4-amino-3-methylpyridine)diisothiocyanatozinc(II) top
Crystal data top
[Zn(NCS)2(C6H8N2)2]F(000) = 816
Mr = 397.82Dx = 1.490 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2289 reflections
a = 8.5622 (4) Åθ = 2.8–28.3°
b = 14.0393 (7) ŵ = 1.63 mm1
c = 14.7524 (7) ÅT = 293 K
V = 1773.35 (15) Å3Block, pale yellow
Z = 40.48 × 0.46 × 0.42 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2289 independent reflections
Radiation source: fine-focus sealed tube1934 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 1011
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1118
Tmin = 0.463, Tmax = 0.505l = 1919
10596 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.047P)2 + 0.5026P]
where P = (Fo2 + 2Fc2)/3
2289 reflections(Δ/σ)max < 0.001
116 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.65 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
Zn10.45747 (4)0.25000.01343 (2)0.04707 (12)
S10.92157 (10)0.25000.17729 (7)0.0723 (3)
S20.65016 (10)0.25000.28672 (6)0.0644 (2)
N10.33599 (19)0.12917 (11)0.02882 (11)0.0465 (3)
N20.6260 (3)0.25000.10362 (18)0.0568 (6)
N30.5378 (3)0.25000.11081 (19)0.0629 (7)
N40.0972 (3)0.12616 (13)0.05599 (16)0.0721 (6)
H4A0.08810.16310.00980.087*
H4B0.05630.14200.10700.087*
C10.3200 (3)0.06834 (14)0.04058 (13)0.0532 (5)
H1A0.36360.08470.09620.064*
C20.2431 (3)0.01615 (15)0.03376 (15)0.0591 (5)
H2B0.23550.05590.08400.071*
C30.1757 (2)0.04340 (13)0.04835 (14)0.0512 (4)
C40.1920 (2)0.01951 (14)0.12261 (13)0.0494 (4)
C50.2722 (3)0.10244 (14)0.10829 (13)0.0515 (4)
H5A0.28370.14350.15730.062*
C60.1228 (4)0.00322 (18)0.21357 (16)0.0747 (7)
H6A0.14050.04910.25420.112*
H6B0.17110.05960.23750.112*
H6C0.01250.01370.20720.112*
C70.7486 (3)0.25000.13499 (16)0.0422 (5)
C80.5835 (3)0.25000.1842 (2)0.0459 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.04847 (19)0.04450 (18)0.04825 (19)0.0000.00294 (13)0.000
S10.0572 (5)0.0813 (6)0.0783 (6)0.0000.0187 (4)0.000
S20.0624 (5)0.0733 (5)0.0575 (4)0.0000.0149 (4)0.000
N10.0532 (8)0.0403 (8)0.0459 (8)0.0006 (7)0.0020 (7)0.0028 (6)
N20.0572 (14)0.0560 (13)0.0571 (14)0.0000.0100 (11)0.000
N30.0575 (15)0.0779 (18)0.0532 (14)0.0000.0018 (11)0.000
N40.0983 (15)0.0417 (9)0.0763 (13)0.0107 (10)0.0184 (12)0.0042 (9)
C10.0705 (12)0.0446 (10)0.0446 (9)0.0011 (9)0.0073 (9)0.0045 (8)
C20.0843 (14)0.0426 (10)0.0503 (10)0.0037 (10)0.0072 (10)0.0119 (8)
C30.0615 (11)0.0350 (9)0.0571 (11)0.0081 (8)0.0025 (9)0.0013 (8)
C40.0610 (11)0.0455 (9)0.0417 (9)0.0066 (8)0.0016 (8)0.0041 (8)
C50.0651 (12)0.0484 (10)0.0410 (9)0.0013 (9)0.0057 (8)0.0060 (8)
C60.1060 (19)0.0706 (15)0.0476 (11)0.0066 (14)0.0089 (12)0.0083 (10)
C70.0569 (15)0.0352 (11)0.0345 (11)0.0000.0010 (11)0.000
C80.0372 (12)0.0449 (13)0.0556 (15)0.0000.0016 (11)0.000
Geometric parameters (Å, º) top
Zn1—N31.958 (3)C1—C21.360 (3)
Zn1—N21.963 (3)C1—H1A0.9300
Zn1—N12.0028 (16)C2—C31.395 (3)
S1—C71.607 (3)C2—H2B0.9300
S2—C81.616 (3)C3—C41.414 (3)
N1—C11.340 (2)C4—C51.368 (3)
N1—C51.347 (2)C4—C61.501 (3)
N2—C71.147 (4)C5—H5A0.9300
N3—C81.152 (4)C6—H6A0.9600
N4—C31.347 (3)C6—H6B0.9600
N4—H4A0.8600C6—H6C0.9600
N4—H4B0.8600
N3—Zn1—N2112.11 (11)N4—C3—C2121.03 (19)
N3—Zn1—N1106.77 (6)N4—C3—C4121.55 (19)
N2—Zn1—N1107.76 (6)C2—C3—C4117.42 (18)
N1—Zn1—N1i115.78 (9)C5—C4—C3117.47 (18)
C1—N1—C5116.49 (17)C5—C4—C6121.14 (19)
C1—N1—Zn1120.42 (14)C3—C4—C6121.38 (19)
C5—N1—Zn1123.04 (13)N1—C5—C4125.11 (17)
C7—N2—Zn1161.1 (2)N1—C5—H5A117.4
C8—N3—Zn1179.3 (3)C4—C5—H5A117.4
C3—N4—H4A120.0C4—C6—H6A109.5
C3—N4—H4B120.0C4—C6—H6B109.5
H4A—N4—H4B120.0H6A—C6—H6B109.5
N1—C1—C2123.28 (19)C4—C6—H6C109.5
N1—C1—H1A118.4H6A—C6—H6C109.5
C2—C1—H1A118.4H6B—C6—H6C109.5
C1—C2—C3120.22 (19)N2—C7—S1179.1 (2)
C1—C2—H2B119.9N3—C8—S2179.2 (3)
C3—C2—H2B119.9
N3—Zn1—N1—C11.66 (18)N1—C1—C2—C30.1 (4)
N2—Zn1—N1—C1122.27 (17)C1—C2—C3—N4179.0 (2)
N1i—Zn1—N1—C1117.04 (15)C1—C2—C3—C40.5 (3)
N3—Zn1—N1—C5175.57 (16)N4—C3—C4—C5179.3 (2)
N2—Zn1—N1—C554.96 (18)C2—C3—C4—C50.2 (3)
N1i—Zn1—N1—C565.73 (19)N4—C3—C4—C60.2 (3)
N3—Zn1—N2—C70.0C2—C3—C4—C6179.7 (2)
N1—Zn1—N2—C7117.20 (5)C1—N1—C5—C40.9 (3)
N1i—Zn1—N2—C7117.20 (5)Zn1—N1—C5—C4178.19 (15)
N2—Zn1—N3—C8180.000 (17)C3—C4—C5—N10.5 (3)
N1—Zn1—N3—C862.21 (6)C6—C4—C5—N1179.0 (2)
N1i—Zn1—N3—C862.21 (5)Zn1—N2—C7—S10.001 (7)
C5—N1—C1—C20.5 (3)Zn1—N3—C8—S2180.000 (9)
Zn1—N1—C1—C2177.92 (18)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···S2ii0.862.813.591 (2)152
Symmetry code: (ii) x+1/2, y, z+1/2.
 

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