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Zinc thio­cyanate complexes have been found to be biologically active compounds. Zinc is also an essential element for the normal function of most organisms and is the main constituent in a number of metalloenzyme proteins. Pyrimidine and amino­pyrimidine derivatives are biologically very important as they are components of nucleic acids. Thio­cyanate ions can bridge metal ions by employing both their N and S atoms for coordination. They can play an important role in assembling different coordination structures and yield an inter­esting variety of one-, two- and three-dimensional polymeric metal–thio­cyanate supra­molecular frameworks. The structure of a new zinc thio­cyanate–amino­pyrimidine organic–inorganic compound, (C6H9ClN3)2[Zn(NCS)4]·2C6H8ClN3·2H2O, is reported. The asymmetric unit consist of half a tetra­thio­cyanato­zinc(II) dianion, an uncoordinated 4-amino-5-chloro-2,6-di­methyl­pyrimidinium cation, a 4-amino-5-chloro-2,6-di­methyl­pyrimidine mol­ecule and a water mol­ecule. The ZnII atom adopts a distorted tetra­hedral coordination geometry and is coordinated by four N atoms from the thio­cyanate anions. The ZnII atom is located on a special position (twofold axis of symmetry). The pyrimidinium cation and the pyrimidine mol­ecule are not coordinated to the ZnII atom, but are hydrogen bonded to the uncoordinated water mol­ecules and the metal-coordinated thio­cyanate ligands. The pyrimidine mol­ecules and pyrimidinium cations also form base-pair-like structures with an R22(8) ring motif via N—H...N hydrogen bonds. The crystal structure is further stabilized by inter­molecular N—H...O, O—H...S, N—H...S and O—H...N hydrogen bonds, by intra­molecular N—H...Cl and C—H...Cl hydrogen bonds, and also by π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004186/cu3096sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004186/cu3096Isup2.hkl
Contains datablock I

CCDC reference: 1465056

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Bis(4-amino-5-chloro-2,6-dimethylpyrimidinium) tetrathiocyanatozinc(II)–4-amino-5-chloro-2,6-dimethylpyrimidine–water (1/2/2) top
Crystal data top
(C6H9ClN3)[Zn(NCS)4]·2C6H8ClN3·2H2OF(000) = 1984
Mr = 966.15Dx = 1.477 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 19.4354 (7) ÅCell parameters from 8426 reflections
b = 16.7556 (6) Åθ = 2.4–30.5°
c = 15.3266 (6) ŵ = 1.05 mm1
β = 119.4829 (11)°T = 100 K
V = 4344.8 (3) Å3Block, colourless
Z = 40.27 × 0.21 × 0.13 mm
Data collection top
Bruker D8 Quest CMOS
diffractometer
6507 independent reflections
Radiation source: I-mu-S microsource X-ray tube4548 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromatorRint = 0.054
ω and φ scansθmax = 30.6°, θmin = 2.4°
Absorption correction: multi-scan
(APEX2; Bruker, 2014)
h = 2725
Tmin = 0.664, Tmax = 0.746k = 2323
25175 measured reflectionsl = 1921
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)] = 0.046Hydrogen site location: mixed
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0317P)2 + 7.8231P]
where P = (Fo2 + 2Fc2)/3
6507 reflections(Δ/σ)max < 0.001
259 parametersΔρmax = 0.43 e Å3
2 restraintsΔρmin = 0.41 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.11718 (13)0.10092 (13)0.38335 (17)0.0229 (5)
C20.04852 (13)0.36488 (14)0.15248 (17)0.0225 (5)
N10.08331 (12)0.15844 (12)0.34275 (17)0.0326 (5)
N20.03536 (12)0.30479 (12)0.17978 (16)0.0297 (5)
O10.24989 (10)0.01341 (10)0.21097 (13)0.0255 (4)
H1A0.2945 (12)0.0248 (17)0.2575 (17)0.038*
H1B0.2567 (17)0.0244 (14)0.180 (2)0.038*
S10.16709 (4)0.02232 (3)0.44438 (5)0.02800 (14)
S20.06662 (4)0.44762 (3)0.11161 (4)0.02462 (13)
Zn10.00000.23105 (2)0.25000.02289 (10)
N1A0.34484 (10)0.36431 (10)0.37009 (13)0.0184 (4)
H1N0.31640.40780.35930.022*
C2A0.41367 (13)0.36956 (13)0.36986 (16)0.0192 (4)
N3A0.45872 (10)0.30678 (10)0.38336 (13)0.0179 (4)
C4A0.43393 (12)0.23410 (12)0.39739 (16)0.0170 (4)
C5A0.36274 (13)0.22810 (12)0.40210 (16)0.0174 (4)
C6A0.31731 (12)0.29419 (13)0.38638 (16)0.0177 (4)
C7A0.43807 (14)0.44973 (13)0.3525 (2)0.0269 (5)
H7AA0.49310.44760.36720.040*
H7AB0.43310.48890.39650.040*
H7AC0.40400.46530.28240.040*
C8A0.23945 (13)0.29757 (14)0.38287 (18)0.0237 (5)
H8AA0.20020.32200.31960.036*
H8AB0.24430.32960.43910.036*
H8AC0.22250.24340.38750.036*
Cl1A0.33386 (3)0.13573 (3)0.42265 (5)0.02680 (13)
N4A0.47755 (11)0.17171 (11)0.40456 (15)0.0233 (4)
H4A10.52080.17790.40030.028*
H4A20.46350.12380.41360.028*
N1B0.28300 (10)0.11725 (11)0.13255 (14)0.0191 (4)
C2B0.35036 (12)0.12117 (12)0.12934 (16)0.0168 (4)
N3B0.38674 (10)0.18820 (10)0.12723 (13)0.0167 (4)
C4B0.35258 (12)0.25812 (12)0.12673 (15)0.0165 (4)
C5B0.28012 (12)0.25815 (12)0.12759 (16)0.0170 (4)
C6B0.24691 (12)0.18685 (13)0.13106 (16)0.0179 (4)
C7B0.38767 (14)0.04338 (13)0.12699 (19)0.0244 (5)
H7BA0.41310.04910.08580.037*
H7BB0.34690.00190.09830.037*
H7BC0.42730.02830.19530.037*
C8B0.17104 (14)0.17983 (14)0.13403 (19)0.0259 (5)
H8BA0.14200.23040.11260.039*
H8BB0.18280.16750.20250.039*
H8BC0.13870.13700.08890.039*
Cl1B0.23541 (3)0.34875 (3)0.12316 (4)0.02473 (13)
N4B0.38898 (11)0.32520 (10)0.12500 (14)0.0226 (4)
H4B10.43390.32280.12420.027*
H4B20.36800.37180.12460.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0204 (11)0.0214 (11)0.0217 (12)0.0055 (9)0.0062 (10)0.0041 (9)
C20.0179 (10)0.0260 (12)0.0193 (11)0.0077 (9)0.0060 (9)0.0005 (9)
N10.0258 (11)0.0246 (11)0.0343 (12)0.0006 (9)0.0048 (10)0.0048 (9)
N20.0263 (11)0.0291 (11)0.0319 (12)0.0061 (9)0.0130 (9)0.0062 (9)
O10.0242 (8)0.0232 (8)0.0265 (9)0.0089 (7)0.0104 (7)0.0021 (7)
S10.0309 (3)0.0168 (3)0.0271 (3)0.0021 (2)0.0072 (3)0.0002 (2)
S20.0273 (3)0.0199 (3)0.0242 (3)0.0060 (2)0.0107 (3)0.0025 (2)
Zn10.01937 (19)0.01837 (18)0.0243 (2)0.0000.00560 (16)0.000
N1A0.0158 (9)0.0164 (9)0.0205 (10)0.0052 (7)0.0070 (8)0.0006 (7)
C2A0.0190 (10)0.0180 (10)0.0183 (11)0.0024 (8)0.0074 (9)0.0004 (8)
N3A0.0178 (9)0.0177 (9)0.0175 (9)0.0021 (7)0.0082 (7)0.0012 (7)
C4A0.0189 (10)0.0185 (10)0.0137 (10)0.0030 (8)0.0082 (8)0.0012 (8)
C5A0.0198 (10)0.0169 (10)0.0163 (10)0.0002 (8)0.0094 (9)0.0006 (8)
C6A0.0168 (10)0.0211 (10)0.0143 (10)0.0005 (8)0.0069 (9)0.0022 (8)
C7A0.0253 (12)0.0171 (11)0.0397 (15)0.0019 (9)0.0169 (11)0.0026 (10)
C8A0.0180 (11)0.0259 (12)0.0283 (13)0.0009 (9)0.0122 (10)0.0020 (10)
Cl1A0.0304 (3)0.0187 (3)0.0396 (3)0.0007 (2)0.0235 (3)0.0031 (2)
N4A0.0258 (10)0.0169 (9)0.0364 (12)0.0057 (8)0.0223 (9)0.0063 (8)
N1B0.0195 (9)0.0184 (9)0.0220 (10)0.0009 (7)0.0124 (8)0.0009 (7)
C2B0.0171 (10)0.0167 (10)0.0170 (11)0.0001 (8)0.0088 (9)0.0004 (8)
N3B0.0176 (9)0.0159 (8)0.0182 (9)0.0006 (7)0.0099 (7)0.0000 (7)
C4B0.0199 (10)0.0165 (10)0.0119 (10)0.0003 (8)0.0070 (8)0.0002 (8)
C5B0.0200 (10)0.0169 (10)0.0143 (10)0.0042 (8)0.0085 (9)0.0012 (8)
C6B0.0165 (10)0.0220 (11)0.0144 (10)0.0000 (8)0.0071 (9)0.0017 (8)
C7B0.0254 (12)0.0182 (11)0.0364 (14)0.0027 (9)0.0205 (11)0.0023 (10)
C8B0.0222 (11)0.0302 (12)0.0314 (14)0.0006 (10)0.0179 (11)0.0024 (10)
Cl1B0.0307 (3)0.0211 (3)0.0240 (3)0.0088 (2)0.0147 (2)0.0002 (2)
N4B0.0258 (10)0.0154 (9)0.0296 (11)0.0016 (7)0.0160 (9)0.0010 (8)
Geometric parameters (Å, º) top
C1—N11.160 (3)C8A—H8AA0.9800
C1—S11.630 (2)C8A—H8AB0.9800
C2—N21.166 (3)C8A—H8AC0.9800
C2—S21.629 (3)N4A—H4A10.8800
N1—Zn11.964 (2)N4A—H4A20.8800
N2—Zn11.971 (2)N1B—C2B1.336 (3)
O1—H1A0.829 (17)N1B—C6B1.355 (3)
O1—H1B0.840 (17)C2B—N3B1.336 (3)
Zn1—N1i1.964 (2)C2B—C7B1.501 (3)
Zn1—N2i1.971 (2)N3B—C4B1.345 (3)
N1A—C2A1.342 (3)C4B—N4B1.335 (3)
N1A—C6A1.364 (3)C4B—C5B1.415 (3)
N1A—H1N0.8800C5B—C6B1.371 (3)
C2A—N3A1.318 (3)C5B—Cl1B1.734 (2)
C2A—C7A1.491 (3)C6B—C8B1.502 (3)
N3A—C4A1.365 (3)C7B—H7BA0.9800
C4A—N4A1.316 (3)C7B—H7BB0.9800
C4A—C5A1.424 (3)C7B—H7BC0.9800
C5A—C6A1.362 (3)C8B—H8BA0.9800
C5A—Cl1A1.727 (2)C8B—H8BB0.9800
C6A—C8A1.489 (3)C8B—H8BC0.9800
C7A—H7AA0.9800N4B—H4B10.8800
C7A—H7AB0.9800N4B—H4B20.8800
C7A—H7AC0.9800
N1—C1—S1177.7 (2)C6A—C8A—H8AC109.5
N2—C2—S2178.4 (2)H8AA—C8A—H8AC109.5
C1—N1—Zn1161.95 (19)H8AB—C8A—H8AC109.5
C2—N2—Zn1159.1 (2)C4A—N4A—H4A1120.0
H1A—O1—H1B106 (3)C4A—N4A—H4A2120.0
N1—Zn1—N1i103.44 (12)H4A1—N4A—H4A2120.0
N1—Zn1—N2i112.20 (9)C2B—N1B—C6B117.74 (18)
N1i—Zn1—N2i113.50 (9)N1B—C2B—N3B125.61 (19)
N1—Zn1—N2113.50 (9)N1B—C2B—C7B116.88 (18)
N1i—Zn1—N2112.20 (9)N3B—C2B—C7B117.51 (18)
N2i—Zn1—N2102.37 (12)C2B—N3B—C4B117.83 (18)
C2A—N1A—C6A122.56 (18)N4B—C4B—N3B117.94 (19)
C2A—N1A—H1N118.7N4B—C4B—C5B122.64 (19)
C6A—N1A—H1N118.7N3B—C4B—C5B119.42 (18)
N3A—C2A—N1A122.2 (2)C6B—C5B—C4B119.32 (19)
N3A—C2A—C7A120.1 (2)C6B—C5B—Cl1B121.87 (16)
N1A—C2A—C7A117.66 (19)C4B—C5B—Cl1B118.81 (16)
C2A—N3A—C4A118.54 (18)N1B—C6B—C5B120.05 (19)
N4A—C4A—N3A117.31 (19)N1B—C6B—C8B116.09 (19)
N4A—C4A—C5A122.80 (19)C5B—C6B—C8B123.9 (2)
N3A—C4A—C5A119.88 (18)C2B—C7B—H7BA109.5
C6A—C5A—C4A119.67 (19)C2B—C7B—H7BB109.5
C6A—C5A—Cl1A121.35 (17)H7BA—C7B—H7BB109.5
C4A—C5A—Cl1A118.92 (16)C2B—C7B—H7BC109.5
C5A—C6A—N1A117.02 (19)H7BA—C7B—H7BC109.5
C5A—C6A—C8A126.6 (2)H7BB—C7B—H7BC109.5
N1A—C6A—C8A116.35 (19)C6B—C8B—H8BA109.5
C2A—C7A—H7AA109.5C6B—C8B—H8BB109.5
C2A—C7A—H7AB109.5H8BA—C8B—H8BB109.5
H7AA—C7A—H7AB109.5C6B—C8B—H8BC109.5
C2A—C7A—H7AC109.5H8BA—C8B—H8BC109.5
H7AA—C7A—H7AC109.5H8BB—C8B—H8BC109.5
H7AB—C7A—H7AC109.5C4B—N4B—H4B1120.0
C6A—C8A—H8AA109.5C4B—N4B—H4B2120.0
C6A—C8A—H8AB109.5H4B1—N4B—H4B2120.0
H8AA—C8A—H8AB109.5
C6A—N1A—C2A—N3A1.4 (3)C6B—N1B—C2B—N3B1.7 (3)
C6A—N1A—C2A—C7A179.2 (2)C6B—N1B—C2B—C7B177.67 (19)
N1A—C2A—N3A—C4A0.4 (3)N1B—C2B—N3B—C4B1.1 (3)
C7A—C2A—N3A—C4A178.9 (2)C7B—C2B—N3B—C4B178.3 (2)
C2A—N3A—C4A—N4A176.0 (2)C2B—N3B—C4B—N4B179.76 (19)
C2A—N3A—C4A—C5A3.1 (3)C2B—N3B—C4B—C5B0.5 (3)
N4A—C4A—C5A—C6A174.9 (2)N4B—C4B—C5B—C6B178.9 (2)
N3A—C4A—C5A—C6A4.0 (3)N3B—C4B—C5B—C6B1.4 (3)
N4A—C4A—C5A—Cl1A2.4 (3)N4B—C4B—C5B—Cl1B1.6 (3)
N3A—C4A—C5A—Cl1A178.60 (15)N3B—C4B—C5B—Cl1B178.10 (15)
C4A—C5A—C6A—N1A2.2 (3)C2B—N1B—C6B—C5B0.8 (3)
Cl1A—C5A—C6A—N1A179.51 (16)C2B—N1B—C6B—C8B179.6 (2)
C4A—C5A—C6A—C8A176.3 (2)C4B—C5B—C6B—N1B0.7 (3)
Cl1A—C5A—C6A—C8A1.0 (3)Cl1B—C5B—C6B—N1B178.75 (16)
C2A—N1A—C6A—C5A0.4 (3)C4B—C5B—C6B—C8B178.9 (2)
C2A—N1A—C6A—C8A179.1 (2)Cl1B—C5B—C6B—C8B1.6 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···S2ii0.83 (2)2.49 (2)3.316 (2)175 (3)
O1—H1B···N1B0.84 (3)1.89 (3)2.723 (2)170 (3)
N1A—H1N···O1iii0.881.792.623 (2)158
N4A—H4A1···N3Biv0.882.052.922 (3)173
N4B—H4B1···N3Aiv0.882.163.041 (3)175
N4B—H4B2···S1iii0.882.693.4766 (18)150
N4A—H4A2···Cl1A0.882.603.000 (2)109
N4B—H4B2···Cl1B0.882.602.997 (2)109
C8A—H8AC···Cl1A0.982.663.161 (2)112
C8B—H8BA···Cl1B0.982.643.132 (2)111
Symmetry codes: (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1, y, z+1/2.
 

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