Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040780/br2052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040780/br2052Isup2.hkl |
CCDC reference: 660158
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.036
- wR factor = 0.104
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 800 Deg. PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C2 - C7 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C6 - C7 ... 1.38 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O2B .. C9A .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. O3 .. 2.66 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see: Bulut et al. (2007).
For related literature, see: Bernstein et al. (1995).
A solution of histamine (2 mmol, 0.222 g) in water (10 ml) was added dropwise upon stirring to the mixture of sodium saccharinate (2 mmol, 0.412 g) and NiCl2·H2O (1 mmol, 0.238 g) in distilled water (30 ml). The solution was heated to 60°C in a temperature-controlled bath and stirred for 8 h at 60°C and then filtered. The blue filtrates were left about two weaks at room temperature, and then the blue crystals of title complex suitable for X-ray diffraction analyses were collected.
The sulfonyl group of sacharinate ligand and the histamine ligand show disorder, which is modelled as two different orientations (C8A—C11A, C8B—C11B; S1A—S1B; O1A—O2A, O1B—O2B) with occupancy factors of 0.507 (8) and 0. 493 (8). All H atoms except those bonded to N4 atom were placed in geometricaly idealized positions, [N—H = 0.90 Å; C—H = 0.93 - 0.97 Å], and refined as riding atoms.
The title compound, (I), is composed of discrete [C24H26N8NiO6S2] molecules. As shown in Figure 1, the nickel atom lies on a center of symmetry and is coordinated by four N atoms of two bidentate histamine ligands and monodentate saccharinato ligands. The geometry around the Ni(II) ion is an elongated octahedron. Related bond distances and angles are given in Table 1. The equatorial plane (N2/N3/N2i/N3i) is formed by N atoms of histamine ligands while the axial positions are occupied by saccharinate N atoms. It is observed that the apical Ni–N bond distance is longer than the basal Ni–N bond distances. The intraligand bond distances are comparable to those observed in the complex [C24H26N8CuO6S2] (Bulut et al., 2007).
Histamine ligand and sulfonyl group of saccharinato ligand show disorder, which is modelled as two different orientations with the occupancy factors of 0.493 (8) for conformer A and 0.507 (8) for conformer B. Both conformers, being inversion isomers, have similiar bond angles and distances. These values are also in good agreement with those found in [C24H26N8CuO6S2] (Bulut et al., 2007).
The molecular packing is stabilized by intra- and inter-molecular hydrogen bonds (Table 2). The neutral complexes are linked by N—H···O hydrogen bonding interactions between the imidazole N atoms of histamine and sacchatinate sulfonyl O atoms. As is seen from Figure 2, imidazol atom N4 acts as a donor atom, via H4a, to atom O2a, producing a chain C(8) (Bernstein et al., 1995) running parallel to the direction [110] and centrosymmetric [R22(16)] rings centered at (n+1/2, n+1/2, 0) (n=zero or integer).
For a related structure, see: Bulut et al. (2007).
For related literature, see: Bernstein et al. (1995).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Ni(C7H4NO3S)2(C5H9N3)2] | Z = 1 |
Mr = 645.36 | F(000) = 334 |
Triclinic, P1 | Dx = 1.577 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7508 (8) Å | Cell parameters from 25242 reflections |
b = 8.9840 (9) Å | θ = 2.0–28.1° |
c = 10.8167 (11) Å | µ = 0.92 mm−1 |
α = 93.728 (8)° | T = 296 K |
β = 103.541 (8)° | Prism, grey |
γ = 109.994 (8)° | 0.52 × 0.47 × 0.28 mm |
V = 679.40 (13) Å3 |
Stoe IPDS II diffractometer | 2667 independent reflections |
Radiation source: fine-focus sealed tube | 2420 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
rotation method scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −8→9 |
Tmin = 0.629, Tmax = 0.878 | k = −11→11 |
9525 measured reflections | l = −13→13 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3 |
2667 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
[Ni(C7H4NO3S)2(C5H9N3)2] | γ = 109.994 (8)° |
Mr = 645.36 | V = 679.40 (13) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.7508 (8) Å | Mo Kα radiation |
b = 8.9840 (9) Å | µ = 0.92 mm−1 |
c = 10.8167 (11) Å | T = 296 K |
α = 93.728 (8)° | 0.52 × 0.47 × 0.28 mm |
β = 103.541 (8)° |
Stoe IPDS II diffractometer | 2667 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2420 reflections with I > 2σ(I) |
Tmin = 0.629, Tmax = 0.878 | Rint = 0.050 |
9525 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.92 e Å−3 |
2667 reflections | Δρmin = −0.76 e Å−3 |
255 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.03453 (14) | |
S1A | −0.0051 (8) | 0.1787 (6) | −0.2688 (4) | 0.0409 (7) | 0.493 (8) |
O1A | 0.0482 (13) | 0.0628 (9) | −0.3309 (8) | 0.0616 (17) | 0.493 (8) |
O2A | 0.1427 (12) | 0.3296 (11) | −0.2139 (9) | 0.0681 (18) | 0.493 (8) |
S1B | −0.0059 (9) | 0.2164 (7) | −0.2538 (6) | 0.0552 (10) | 0.507 (8) |
O1B | 0.0969 (14) | 0.1302 (12) | −0.3034 (11) | 0.086 (3) | 0.507 (8) |
O2B | 0.1140 (13) | 0.3761 (10) | −0.1841 (10) | 0.081 (2) | 0.507 (8) |
O3 | −0.4308 (2) | 0.0515 (2) | −0.14797 (16) | 0.0563 (4) | |
N1 | −0.1265 (2) | 0.1088 (2) | −0.16691 (16) | 0.0415 (4) | |
N2 | −0.1652 (2) | 0.0732 (2) | 0.10049 (17) | 0.0436 (4) | |
H2A | −0.2647 | 0.0790 | 0.0412 | 0.052* | |
H2B | −0.2134 | −0.0065 | 0.1435 | 0.052* | |
N3 | 0.2278 (2) | 0.21908 (19) | 0.07337 (16) | 0.0424 (4) | |
N4 | 0.5050 (3) | 0.4154 (2) | 0.1223 (2) | 0.0558 (5) | |
H4A | 0.610 (5) | 0.466 (4) | 0.120 (3) | 0.063 (8)* | |
C1 | −0.3102 (3) | 0.1008 (2) | −0.20708 (19) | 0.0407 (4) | |
C2 | −0.3531 (3) | 0.1607 (2) | −0.33201 (19) | 0.0432 (4) | |
C3 | −0.5258 (4) | 0.1636 (3) | −0.4027 (2) | 0.0565 (6) | |
H3 | −0.6357 | 0.1240 | −0.3753 | 0.068* | |
C4 | −0.5279 (5) | 0.2278 (4) | −0.5159 (3) | 0.0742 (8) | |
H4 | −0.6418 | 0.2314 | −0.5651 | 0.089* | |
C5 | −0.3669 (6) | 0.2860 (5) | −0.5571 (3) | 0.0812 (9) | |
H5 | −0.3740 | 0.3276 | −0.6338 | 0.097* | |
C6 | −0.1946 (5) | 0.2844 (4) | −0.4874 (3) | 0.0709 (7) | |
H6 | −0.0847 | 0.3246 | −0.5147 | 0.085* | |
C7 | −0.1933 (3) | 0.2200 (3) | −0.3749 (2) | 0.0489 (5) | |
C8A | −0.0828 (13) | 0.2245 (12) | 0.1936 (8) | 0.064 (2) | 0.507 (8) |
H8A1 | 0.0066 | 0.2144 | 0.2690 | 0.077* | 0.507 (8) |
H8A2 | −0.1835 | 0.2462 | 0.2211 | 0.077* | 0.507 (8) |
C9A | 0.0179 (9) | 0.3599 (6) | 0.1310 (6) | 0.069 (2) | 0.507 (8) |
H9A1 | −0.0636 | 0.3532 | 0.0461 | 0.083* | 0.507 (8) |
H9A2 | 0.0387 | 0.4608 | 0.1815 | 0.083* | 0.507 (8) |
C10A | 0.2042 (9) | 0.3590 (7) | 0.1182 (7) | 0.0509 (13) | 0.507 (8) |
C11A | 0.3791 (13) | 0.4790 (9) | 0.1533 (8) | 0.0593 (18) | 0.507 (8) |
H11A | 0.4081 | 0.5837 | 0.1911 | 0.071* | 0.507 (8) |
C8B | −0.1115 (12) | 0.2479 (9) | 0.1411 (8) | 0.0513 (17) | 0.493 (8) |
H8B1 | −0.2045 | 0.2656 | 0.1805 | 0.062* | 0.493 (8) |
H8B2 | −0.1106 | 0.3021 | 0.0664 | 0.062* | 0.493 (8) |
C9B | 0.0827 (7) | 0.3149 (6) | 0.2356 (5) | 0.0582 (16) | 0.493 (8) |
H9B1 | 0.1016 | 0.4193 | 0.2793 | 0.070* | 0.493 (8) |
H9B2 | 0.0886 | 0.2451 | 0.2999 | 0.070* | 0.493 (8) |
C10B | 0.2398 (8) | 0.3316 (6) | 0.1739 (7) | 0.0466 (13) | 0.493 (8) |
C11B | 0.4107 (13) | 0.4534 (10) | 0.1985 (9) | 0.0583 (19) | 0.493 (8) |
H11B | 0.4538 | 0.5466 | 0.2580 | 0.070* | 0.493 (8) |
C12 | 0.4010 (3) | 0.2674 (3) | 0.0614 (2) | 0.0508 (5) | |
H12 | 0.4465 | 0.2052 | 0.0155 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0241 (2) | 0.0339 (2) | 0.0429 (2) | 0.00635 (14) | 0.01269 (14) | −0.00122 (12) |
S1A | 0.0276 (10) | 0.0488 (17) | 0.0456 (8) | 0.0100 (10) | 0.0132 (6) | 0.0131 (9) |
O1A | 0.059 (4) | 0.082 (4) | 0.062 (2) | 0.033 (3) | 0.036 (2) | 0.017 (3) |
O2A | 0.038 (3) | 0.070 (4) | 0.069 (3) | −0.011 (3) | 0.010 (2) | 0.009 (3) |
S1B | 0.0346 (11) | 0.059 (2) | 0.083 (2) | 0.0180 (15) | 0.0297 (13) | 0.0301 (16) |
O1B | 0.074 (6) | 0.122 (7) | 0.118 (7) | 0.066 (5) | 0.071 (5) | 0.069 (5) |
O2B | 0.042 (3) | 0.069 (5) | 0.100 (6) | −0.010 (3) | 0.002 (3) | 0.027 (4) |
O3 | 0.0347 (8) | 0.0821 (11) | 0.0600 (9) | 0.0226 (8) | 0.0235 (7) | 0.0210 (8) |
N1 | 0.0282 (8) | 0.0472 (9) | 0.0481 (9) | 0.0101 (7) | 0.0140 (7) | 0.0094 (7) |
N2 | 0.0326 (9) | 0.0499 (9) | 0.0497 (9) | 0.0144 (7) | 0.0167 (7) | 0.0022 (7) |
N3 | 0.0310 (9) | 0.0375 (8) | 0.0518 (9) | 0.0061 (7) | 0.0102 (7) | 0.0007 (7) |
N4 | 0.0352 (11) | 0.0477 (10) | 0.0655 (12) | −0.0025 (9) | 0.0035 (9) | 0.0148 (9) |
C1 | 0.0319 (10) | 0.0424 (9) | 0.0465 (10) | 0.0117 (8) | 0.0125 (8) | 0.0027 (7) |
C2 | 0.0379 (11) | 0.0458 (10) | 0.0433 (9) | 0.0143 (8) | 0.0101 (8) | −0.0004 (8) |
C3 | 0.0438 (13) | 0.0724 (14) | 0.0528 (12) | 0.0253 (11) | 0.0088 (10) | 0.0011 (10) |
C4 | 0.0726 (19) | 0.103 (2) | 0.0531 (13) | 0.0495 (18) | 0.0033 (13) | 0.0105 (13) |
C5 | 0.096 (2) | 0.109 (2) | 0.0520 (14) | 0.050 (2) | 0.0213 (15) | 0.0295 (15) |
C6 | 0.0681 (19) | 0.0895 (19) | 0.0634 (15) | 0.0288 (16) | 0.0291 (14) | 0.0299 (14) |
C7 | 0.0429 (12) | 0.0527 (11) | 0.0488 (11) | 0.0136 (9) | 0.0141 (9) | 0.0090 (9) |
C8A | 0.059 (5) | 0.079 (5) | 0.058 (4) | 0.028 (3) | 0.025 (4) | −0.017 (4) |
C9A | 0.066 (4) | 0.049 (3) | 0.092 (4) | 0.024 (3) | 0.023 (3) | −0.013 (2) |
C10A | 0.049 (3) | 0.042 (2) | 0.053 (3) | 0.011 (2) | 0.010 (3) | −0.006 (2) |
C11A | 0.063 (5) | 0.036 (3) | 0.059 (4) | 0.002 (3) | 0.008 (4) | −0.004 (3) |
C8B | 0.043 (3) | 0.055 (3) | 0.058 (4) | 0.023 (3) | 0.013 (3) | −0.005 (3) |
C9B | 0.050 (3) | 0.061 (3) | 0.057 (3) | 0.020 (2) | 0.008 (2) | −0.014 (2) |
C10B | 0.040 (3) | 0.040 (2) | 0.052 (3) | 0.0142 (19) | 0.002 (2) | −0.001 (2) |
C11B | 0.054 (4) | 0.037 (3) | 0.062 (5) | 0.006 (2) | −0.006 (4) | 0.002 (3) |
C12 | 0.0336 (11) | 0.0471 (11) | 0.0647 (13) | 0.0067 (9) | 0.0133 (9) | 0.0081 (9) |
Ni1—N1 | 2.2874 (19) | C2—C3 | 1.387 (3) |
Ni1—N2 | 2.0944 (19) | C3—C4 | 1.385 (4) |
Ni1—N3 | 2.094 (2) | C3—H3 | 0.9300 |
S1A—O2A | 1.421 (9) | C4—C5 | 1.369 (5) |
S1A—O1A | 1.428 (8) | C4—H4 | 0.9300 |
S1A—N1 | 1.632 (6) | C5—C6 | 1.377 (5) |
S1A—C7 | 1.796 (5) | C5—H5 | 0.9300 |
S1B—O1B | 1.445 (9) | C6—C7 | 1.379 (3) |
S1B—O2B | 1.453 (9) | C6—H6 | 0.9300 |
S1B—N1 | 1.613 (6) | C8A—C9A | 1.501 (12) |
S1B—C7 | 1.725 (6) | C8A—H8A1 | 0.9700 |
O3—C1 | 1.230 (3) | C8A—H8A2 | 0.9700 |
N1—C1 | 1.363 (3) | C9A—C10A | 1.485 (9) |
N2—C8A | 1.483 (8) | C9A—H9A1 | 0.9700 |
N2—C8B | 1.486 (8) | C9A—H9A2 | 0.9700 |
N2—H2A | 0.9000 | C10A—C11A | 1.360 (10) |
N2—H2B | 0.9000 | C11A—H11A | 0.9300 |
N3—C12 | 1.303 (3) | C8B—C9B | 1.501 (10) |
N3—C10B | 1.399 (6) | C8B—H8B1 | 0.9700 |
N3—C10A | 1.403 (6) | C8B—H8B2 | 0.9700 |
N4—C11B | 1.322 (11) | C9B—C10B | 1.490 (8) |
N4—C12 | 1.325 (3) | C9B—H9B1 | 0.9700 |
N4—C11A | 1.379 (10) | C9B—H9B2 | 0.9700 |
N4—H4A | 0.79 (3) | C10B—C11B | 1.352 (11) |
C1—C2 | 1.495 (3) | C11B—H11B | 0.9300 |
C2—C7 | 1.373 (3) | C12—H12 | 0.9300 |
N3—Ni1—N3i | 180.00 (7) | C4—C3—C2 | 117.3 (3) |
N3—Ni1—N2 | 90.30 (10) | C4—C3—H3 | 121.4 |
N3i—Ni1—N2 | 89.70 (10) | C2—C3—H3 | 121.4 |
N3—Ni1—N2i | 89.70 (10) | C5—C4—C3 | 121.7 (3) |
N3i—Ni1—N2i | 90.30 (10) | C5—C4—H4 | 119.1 |
N2—Ni1—N2i | 180.00 (8) | C3—C4—H4 | 119.1 |
N3—Ni1—N1i | 89.27 (9) | C4—C5—C6 | 121.4 (3) |
N3i—Ni1—N1i | 90.73 (9) | C4—C5—H5 | 119.3 |
N2—Ni1—N1i | 93.59 (8) | C6—C5—H5 | 119.3 |
N2i—Ni1—N1i | 86.41 (8) | C5—C6—C7 | 116.6 (3) |
N3—Ni1—N1 | 90.73 (9) | C5—C6—H6 | 121.7 |
N3i—Ni1—N1 | 89.27 (9) | C7—C6—H6 | 121.7 |
N2—Ni1—N1 | 86.41 (8) | C2—C7—C6 | 122.9 (2) |
N2i—Ni1—N1 | 93.59 (8) | C2—C7—S1B | 106.1 (3) |
N1i—Ni1—N1 | 180.00 (7) | C6—C7—S1B | 130.6 (3) |
O2A—S1A—O1A | 116.3 (5) | C2—C7—S1A | 107.5 (2) |
O2A—S1A—N1 | 111.0 (4) | C6—C7—S1A | 129.3 (3) |
O1A—S1A—N1 | 113.5 (5) | N2—C8A—C9A | 109.4 (6) |
O2A—S1A—C7 | 106.4 (5) | N2—C8A—H8A1 | 109.8 |
O1A—S1A—C7 | 112.2 (5) | C9A—C8A—H8A1 | 109.8 |
N1—S1A—C7 | 95.3 (3) | N2—C8A—H8A2 | 109.8 |
O1B—S1B—O2B | 114.1 (6) | C9A—C8A—H8A2 | 109.8 |
O1B—S1B—N1 | 109.1 (5) | H8A1—C8A—H8A2 | 108.2 |
O2B—S1B—N1 | 111.5 (5) | C10A—C9A—C8A | 113.2 (6) |
O1B—S1B—C7 | 110.6 (5) | C10A—C9A—H9A1 | 108.9 |
O2B—S1B—C7 | 111.7 (5) | C8A—C9A—H9A1 | 108.9 |
N1—S1B—C7 | 98.8 (3) | C10A—C9A—H9A2 | 108.9 |
C1—N1—S1B | 108.4 (2) | C8A—C9A—H9A2 | 108.9 |
C1—N1—S1A | 112.1 (2) | H9A1—C9A—H9A2 | 107.8 |
C1—N1—Ni1 | 127.06 (13) | C11A—C10A—N3 | 107.5 (6) |
S1B—N1—Ni1 | 124.5 (2) | C11A—C10A—C9A | 129.8 (6) |
S1A—N1—Ni1 | 120.0 (2) | N3—C10A—C9A | 122.5 (4) |
C8A—N2—Ni1 | 121.5 (4) | C10A—C11A—N4 | 106.8 (6) |
C8B—N2—Ni1 | 118.1 (3) | C10A—C11A—H11A | 126.6 |
C8A—N2—H2A | 106.9 | N4—C11A—H11A | 126.6 |
C8B—N2—H2A | 86.0 | N2—C8B—C9B | 109.7 (5) |
Ni1—N2—H2A | 106.9 | N2—C8B—H8B1 | 109.7 |
C8A—N2—H2B | 106.9 | C9B—C8B—H8B1 | 109.7 |
C8B—N2—H2B | 127.1 | N2—C8B—H8B2 | 109.7 |
Ni1—N2—H2B | 106.9 | C9B—C8B—H8B2 | 109.7 |
H2A—N2—H2B | 106.7 | H8B1—C8B—H8B2 | 108.2 |
C12—N3—C10B | 103.1 (3) | C10B—C9B—C8B | 113.0 (5) |
C12—N3—C10A | 105.0 (3) | C10B—C9B—H9B1 | 109.0 |
C12—N3—Ni1 | 130.02 (15) | C8B—C9B—H9B1 | 109.0 |
C10B—N3—Ni1 | 125.2 (3) | C10B—C9B—H9B2 | 109.0 |
C10A—N3—Ni1 | 123.2 (3) | C8B—C9B—H9B2 | 109.0 |
C11B—N4—C12 | 107.2 (4) | H9B1—C9B—H9B2 | 107.8 |
C12—N4—C11A | 106.3 (4) | C11B—C10B—N3 | 108.2 (6) |
C11B—N4—H4A | 126 (2) | C11B—C10B—C9B | 128.4 (6) |
C12—N4—H4A | 126 (2) | N3—C10B—C9B | 123.4 (4) |
C11A—N4—H4A | 125 (2) | N4—C11B—C10B | 107.3 (7) |
O3—C1—N1 | 124.7 (2) | N4—C11B—H11B | 126.4 |
O3—C1—C2 | 122.09 (19) | C10B—C11B—H11B | 126.4 |
N1—C1—C2 | 113.15 (17) | N3—C12—N4 | 112.3 (2) |
C7—C2—C3 | 120.0 (2) | N3—C12—H12 | 123.9 |
C7—C2—C1 | 111.53 (19) | N4—C12—H12 | 123.9 |
C3—C2—C1 | 128.4 (2) |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.90 | 2.09 | 2.927 (3) | 153 |
N2—H2B···O1Ai | 0.90 | 2.32 | 2.936 (10) | 126 |
N2—H2B···S1Ai | 0.90 | 2.84 | 3.409 (5) | 122 |
N4—H4A···O2Aii | 0.79 (3) | 2.12 (4) | 2.801 (9) | 144 (3) |
N4—H4A···O2Bii | 0.79 (3) | 2.04 (4) | 2.794 (9) | 159 (3) |
N2—H2B···O3iii | 0.90 | 2.66 | 3.123 (4) | 113 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z; (iii) −x−1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C7H4NO3S)2(C5H9N3)2] |
Mr | 645.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.7508 (8), 8.9840 (9), 10.8167 (11) |
α, β, γ (°) | 93.728 (8), 103.541 (8), 109.994 (8) |
V (Å3) | 679.40 (13) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.52 × 0.47 × 0.28 |
Data collection | |
Diffractometer | Stoe IPDS II |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.629, 0.878 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9525, 2667, 2420 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.104, 1.01 |
No. of reflections | 2667 |
No. of parameters | 255 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.92, −0.76 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3 | 0.90 | 2.09 | 2.927 (3) | 153.3 |
N2—H2B···O1Ai | 0.90 | 2.32 | 2.936 (10) | 125.9 |
N2—H2B···S1Ai | 0.90 | 2.84 | 3.409 (5) | 122.2 |
N4—H4A···O2Aii | 0.79 (3) | 2.12 (4) | 2.801 (9) | 144 (3) |
N4—H4A···O2Bii | 0.79 (3) | 2.04 (4) | 2.794 (9) | 159 (3) |
N2—H2B···O3iii | 0.90 | 2.66 | 3.123 (4) | 113.0 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z; (iii) −x−1, −y, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The title compound, (I), is composed of discrete [C24H26N8NiO6S2] molecules. As shown in Figure 1, the nickel atom lies on a center of symmetry and is coordinated by four N atoms of two bidentate histamine ligands and monodentate saccharinato ligands. The geometry around the Ni(II) ion is an elongated octahedron. Related bond distances and angles are given in Table 1. The equatorial plane (N2/N3/N2i/N3i) is formed by N atoms of histamine ligands while the axial positions are occupied by saccharinate N atoms. It is observed that the apical Ni–N bond distance is longer than the basal Ni–N bond distances. The intraligand bond distances are comparable to those observed in the complex [C24H26N8CuO6S2] (Bulut et al., 2007).
Histamine ligand and sulfonyl group of saccharinato ligand show disorder, which is modelled as two different orientations with the occupancy factors of 0.493 (8) for conformer A and 0.507 (8) for conformer B. Both conformers, being inversion isomers, have similiar bond angles and distances. These values are also in good agreement with those found in [C24H26N8CuO6S2] (Bulut et al., 2007).
The molecular packing is stabilized by intra- and inter-molecular hydrogen bonds (Table 2). The neutral complexes are linked by N—H···O hydrogen bonding interactions between the imidazole N atoms of histamine and sacchatinate sulfonyl O atoms. As is seen from Figure 2, imidazol atom N4 acts as a donor atom, via H4a, to atom O2a, producing a chain C(8) (Bernstein et al., 1995) running parallel to the direction [110] and centrosymmetric [R22(16)] rings centered at (n+1/2, n+1/2, 0) (n=zero or integer).