In the title compound, [Zn(NCS)
2(C
4H
7N
3O)
2], the Zn atom is coordinated by two N atoms from two 2-amino-1-methylimidazol-4(5
H)-one (creatinine) ligands and by another two N atoms from two terminal thiocyanate ligands in a slightly distorted tetrahedral geometry. The molecule possesses a crystallographic twofold symmetry axis. In the crystal structure, molecules are linked through intermolecular N—H
O hydrogen bonds to form chains.
Supporting information
CCDC reference: 636773
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.054
- wR factor = 0.143
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C5
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.06
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 60.00 A 3
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
Bis[2-amino-1-methyl-1
H-imidazol-4(5
H)-one-
κN3]dithiocyanatozinc(II)
top
Crystal data top
[Zn(NCS)2(C4H7N3O)2] | F(000) = 832 |
Mr = 407.78 | Dx = 1.439 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.958 (1) Å | Cell parameters from 3043 reflections |
b = 11.628 (2) Å | θ = 2.3–25.4° |
c = 12.794 (2) Å | µ = 1.55 mm−1 |
β = 122.248 (1)° | T = 298 K |
V = 1882.0 (5) Å3 | Block cut from needle, colourless |
Z = 4 | 0.25 × 0.12 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1872 independent reflections |
Radiation source: fine-focus sealed tube | 1668 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 26.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.699, Tmax = 0.861 | k = −14→13 |
6880 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0951P)2 + 0.8797P] where P = (Fo2 + 2Fc2)/3 |
1872 reflections | (Δ/σ)max < 0.001 |
112 parameters | Δρmax = 1.16 e Å−3 |
3 restraints | Δρmin = −0.56 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Zn1 | 0.0000 | 0.32599 (4) | 0.2500 | 0.0433 (2) | |
S1 | −0.1890 (2) | 0.60618 (17) | −0.05145 (19) | 0.1379 (8) | |
O1 | −0.0234 (2) | 0.1445 (3) | 0.0474 (3) | 0.0842 (10) | |
N1 | 0.10040 (19) | 0.2343 (2) | 0.2260 (2) | 0.0465 (6) | |
N2 | 0.2487 (2) | 0.1650 (2) | 0.2460 (3) | 0.0544 (7) | |
N3 | 0.2636 (2) | 0.2992 (3) | 0.3891 (3) | 0.0573 (7) | |
N4 | −0.0860 (2) | 0.4286 (3) | 0.1077 (3) | 0.0611 (7) | |
C1 | 0.0678 (3) | 0.1629 (3) | 0.1294 (4) | 0.0576 (9) | |
C2 | 0.1641 (3) | 0.1096 (3) | 0.1378 (4) | 0.0648 (9) | |
H2A | 0.1657 | 0.0269 | 0.1486 | 0.078* | |
H2B | 0.1665 | 0.1269 | 0.0652 | 0.078* | |
C3 | 0.2082 (2) | 0.2351 (3) | 0.2917 (3) | 0.0435 (6) | |
C4 | 0.3598 (3) | 0.1463 (5) | 0.2927 (4) | 0.0758 (11) | |
H4A | 0.4017 | 0.1734 | 0.3763 | 0.114* | |
H4B | 0.3788 | 0.1874 | 0.2422 | 0.114* | |
H4C | 0.3723 | 0.0656 | 0.2903 | 0.114* | |
C5 | −0.1266 (3) | 0.5027 (3) | 0.0420 (4) | 0.0586 (8) | |
H3B | 0.3325 (11) | 0.294 (4) | 0.446 (3) | 0.080* | |
H3A | 0.230 (3) | 0.337 (4) | 0.420 (4) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0333 (3) | 0.0425 (3) | 0.0512 (3) | 0.000 | 0.0206 (2) | 0.000 |
S1 | 0.200 (2) | 0.1200 (13) | 0.1353 (14) | 0.0905 (14) | 0.1172 (15) | 0.0841 (12) |
O1 | 0.0455 (14) | 0.0851 (18) | 0.086 (2) | 0.0037 (13) | 0.0112 (14) | −0.0301 (16) |
N1 | 0.0343 (11) | 0.0509 (14) | 0.0512 (13) | 0.0042 (10) | 0.0207 (10) | 0.0040 (11) |
N2 | 0.0438 (15) | 0.0634 (17) | 0.0556 (16) | 0.0146 (11) | 0.0263 (13) | 0.0043 (12) |
N3 | 0.0341 (13) | 0.0799 (18) | 0.0533 (16) | 0.0016 (13) | 0.0203 (12) | −0.0051 (14) |
N4 | 0.0536 (16) | 0.0604 (16) | 0.0659 (18) | 0.0113 (13) | 0.0297 (14) | 0.0143 (14) |
C1 | 0.0467 (18) | 0.0545 (18) | 0.062 (2) | 0.0081 (13) | 0.0229 (16) | −0.0040 (14) |
C2 | 0.0546 (19) | 0.068 (2) | 0.066 (2) | 0.0133 (16) | 0.0282 (17) | −0.0065 (17) |
C3 | 0.0350 (13) | 0.0533 (16) | 0.0420 (14) | 0.0054 (11) | 0.0205 (11) | 0.0100 (12) |
C4 | 0.049 (2) | 0.111 (3) | 0.073 (3) | 0.024 (2) | 0.0355 (19) | 0.009 (2) |
C5 | 0.0599 (19) | 0.0598 (19) | 0.068 (2) | 0.0096 (15) | 0.0424 (17) | 0.0135 (17) |
Geometric parameters (Å, º) top
Zn1—N4i | 1.973 (3) | N3—C3 | 1.302 (4) |
Zn1—N4 | 1.973 (3) | N3—H3B | 0.90 (5) |
Zn1—N1 | 1.995 (2) | N3—H3A | 0.90 (5) |
Zn1—N1i | 1.995 (2) | N4—C5 | 1.129 (5) |
S1—C5 | 1.599 (4) | C1—C2 | 1.518 (5) |
O1—C1 | 1.217 (5) | C2—H2A | 0.9700 |
N1—C1 | 1.346 (5) | C2—H2B | 0.9700 |
N1—C3 | 1.364 (3) | C4—H4A | 0.9600 |
N2—C3 | 1.323 (4) | C4—H4B | 0.9600 |
N2—C2 | 1.436 (5) | C4—H4C | 0.9600 |
N2—C4 | 1.451 (5) | | |
| | | |
N4i—Zn1—N4 | 105.6 (2) | N1—C1—C2 | 108.8 (3) |
N4i—Zn1—N1 | 106.95 (12) | N2—C2—C1 | 101.5 (3) |
N4—Zn1—N1 | 110.79 (12) | N2—C2—H2A | 111.5 |
N4i—Zn1—N1i | 110.79 (12) | C1—C2—H2A | 111.5 |
N4—Zn1—N1i | 106.95 (12) | N2—C2—H2B | 111.5 |
N1—Zn1—N1i | 115.38 (15) | C1—C2—H2B | 111.5 |
C1—N1—C3 | 107.4 (3) | H2A—C2—H2B | 109.3 |
C1—N1—Zn1 | 122.5 (2) | N3—C3—N2 | 124.7 (3) |
C3—N1—Zn1 | 129.9 (2) | N3—C3—N1 | 122.2 (3) |
C3—N2—C2 | 109.1 (3) | N2—C3—N1 | 113.1 (3) |
C3—N2—C4 | 127.2 (3) | N2—C4—H4A | 109.5 |
C2—N2—C4 | 123.8 (3) | N2—C4—H4B | 109.5 |
C3—N3—H3B | 128 (3) | H4A—C4—H4B | 109.5 |
C3—N3—H3A | 119 (3) | N2—C4—H4C | 109.5 |
H3B—N3—H3A | 110 (2) | H4A—C4—H4C | 109.5 |
C5—N4—Zn1 | 167.4 (3) | H4B—C4—H4C | 109.5 |
O1—C1—N1 | 126.1 (3) | N4—C5—S1 | 177.3 (4) |
O1—C1—C2 | 125.1 (3) | | |
Symmetry code: (i) −x, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N4i | 0.90 (5) | 2.26 (5) | 3.072 (4) | 150 (4) |
N3—H3B···O1ii | 0.90 (5) | 1.96 (2) | 2.791 (4) | 154 (5) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x+1/2, −y+1/2, z+1/2. |