Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029911/ng2282sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029911/ng2282Isup2.hkl |
CCDC reference: 612868
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.024
- wR factor = 0.068
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N1 .. 5.35 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N2 .. 7.10 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O3 -NI1 -O3 -S1 -153.00 8.00 3.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N1 -NI1 -N1 -C5 8.00 0.00 3.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N1 -NI1 -N1 -C1 10.00 0.00 3.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 N2 -NI1 -N2 -C6 -78.00 17.00 3.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 N2 -NI1 -N2 -C7 160.00 17.00 3.555 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 1.91
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 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 6 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
2-(2-Pyridylmethylamino)ethanesulfonic acid was prepared according to the method of Li et al., 2006). The ligand (2.0 mmol, 0.432 g) was dissolved in water (15 ml). To this solution, NiCl26H2O (1.0 m mol, 0.238 g) was added, and the resulting mixture was stirred at 323 K for 6 h. The solution was filtered; the filtrate was left to stand at room temperature. Green block-shaped crystals were obtained in a yield of 43%. Analysis, found(%): C 39.31; H 4.54; N 11.38; S 13.01. C16H22NiN4O6S2 requires(%): C 39.25; H 4.50; N 11.45; S 13.08. IR(KBr, ν cm-1):771.3[γ(C?C—H)], 746.5(γ CH2); 1189.5, 1149.5, 1035.1(ν SO3-); 1608.7, 1571.8 (ν C? C+C?N); 3213.8 (νN-H).
H atoms bonded to C were positioned geometrically with C—H distance 0.93–0.97 Å, and treated as riding atoms, with Uiso(H)=1.2Ueq(C). The N—H hydrogen atom was located in a difference Fourier map and refined isotropically.
The compound is isostructural with [Co(C8H11N2O3S)2], whose structure has been described in detail (Li et al., 2006).The six-coordiante nickel atom lies on an inversion centre with the two monodeprotonated lingds coordinate in a tridentate facial arrangement with its three donor atoms.
The N—H donor and S?O acceptor groups of the PMT ligand participate in the hydrogen bonding and form a two-dimensional network in the bc plane (Fig. 2 and Table 2).
For the isostuctural cobalt(II) analog, see: Li et al. (2006).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL.
[Ni(C8H11N2O3S)2] | F(000) = 508 |
Mr = 489.21 | Dx = 1.554 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5566 reflections |
a = 9.609 (1) Å | θ = 2.8–28.2° |
b = 9.927 (1) Å | µ = 1.17 mm−1 |
c = 11.4537 (12) Å | T = 291 K |
β = 106.848 (1)° | Block, green |
V = 1045.66 (19) Å3 | 0.35 × 0.26 × 0.22 mm |
Z = 2 |
Bruker APEX II CCD area-detector diffractometer | 2401 independent reflections |
Radiation source: fine-focus sealed tube | 2212 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.683, Tmax = 0.787 | k = −12→12 |
8966 measured reflections | l = −14→14 |
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.3431P] where P = (Fo2 + 2Fc2)/3 |
2401 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
[Ni(C8H11N2O3S)2] | V = 1045.66 (19) Å3 |
Mr = 489.21 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.609 (1) Å | µ = 1.17 mm−1 |
b = 9.927 (1) Å | T = 291 K |
c = 11.4537 (12) Å | 0.35 × 0.26 × 0.22 mm |
β = 106.848 (1)° |
Bruker APEX II CCD area-detector diffractometer | 2401 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2212 reflections with I > 2σ(I) |
Tmin = 0.683, Tmax = 0.787 | Rint = 0.016 |
8966 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.30 e Å−3 |
2401 reflections | Δρmin = −0.38 e Å−3 |
137 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 | ||
Ni1 | 0.0000 | 0.0000 | 0.0000 | 0.02225 (9) | |
S1 | −0.13109 (4) | 0.28994 (4) | 0.04303 (3) | 0.02938 (10) | |
O1 | −0.05360 (16) | 0.39933 (12) | 0.11905 (10) | 0.0458 (3) | |
O2 | −0.28622 (14) | 0.29309 (16) | 0.02363 (14) | 0.0588 (4) | |
O3 | −0.06507 (13) | 0.15954 (11) | 0.09085 (10) | 0.0356 (2) | |
N1 | 0.21837 (14) | 0.03407 (13) | 0.10617 (12) | 0.0303 (3) | |
N2 | 0.07293 (13) | 0.13004 (12) | −0.11590 (11) | 0.0278 (2) | |
C1 | 0.30118 (16) | 0.08851 (16) | 0.04133 (16) | 0.0361 (3) | |
C2 | 0.4419 (2) | 0.1324 (2) | 0.0964 (2) | 0.0603 (6) | |
H2 | 0.4970 | 0.1706 | 0.0503 | 0.072* | |
C3 | 0.4988 (2) | 0.1182 (3) | 0.2214 (2) | 0.0772 (8) | |
H3 | 0.5929 | 0.1473 | 0.2603 | 0.093* | |
C4 | 0.4153 (2) | 0.0608 (3) | 0.2882 (2) | 0.0639 (6) | |
H4 | 0.4525 | 0.0498 | 0.3721 | 0.077* | |
C5 | 0.2757 (2) | 0.01988 (18) | 0.22770 (16) | 0.0405 (4) | |
H5 | 0.2192 | −0.0188 | 0.2724 | 0.049* | |
C6 | 0.22948 (17) | 0.09836 (17) | −0.09381 (15) | 0.0371 (3) | |
H6A | 0.2757 | 0.1685 | −0.1284 | 0.045* | |
H6B | 0.2399 | 0.0137 | −0.1328 | 0.045* | |
C7 | 0.05421 (17) | 0.27742 (14) | −0.10031 (14) | 0.0316 (3) | |
H7A | 0.0786 | 0.3259 | −0.1653 | 0.038* | |
H7B | 0.1206 | 0.3065 | −0.0234 | 0.038* | |
C8 | −0.10033 (17) | 0.31163 (15) | −0.10230 (13) | 0.0303 (3) | |
H8A | −0.1672 | 0.2546 | −0.1615 | 0.036* | |
H8B | −0.1207 | 0.4044 | −0.1282 | 0.036* | |
H1N | 0.0333 (19) | 0.1125 (17) | −0.1905 (17) | 0.033 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.02352 (14) | 0.02147 (14) | 0.02214 (13) | −0.00247 (8) | 0.00720 (10) | 0.00056 (8) |
S1 | 0.0344 (2) | 0.02661 (18) | 0.02887 (18) | 0.00052 (13) | 0.01194 (14) | −0.00103 (13) |
O1 | 0.0754 (9) | 0.0310 (6) | 0.0330 (6) | −0.0097 (6) | 0.0188 (6) | −0.0074 (5) |
O2 | 0.0368 (7) | 0.0803 (11) | 0.0640 (9) | 0.0074 (7) | 0.0221 (6) | 0.0116 (8) |
O3 | 0.0550 (7) | 0.0273 (5) | 0.0282 (5) | 0.0044 (5) | 0.0179 (5) | 0.0016 (4) |
N1 | 0.0269 (6) | 0.0304 (6) | 0.0321 (6) | −0.0018 (5) | 0.0064 (5) | −0.0012 (5) |
N2 | 0.0321 (6) | 0.0272 (6) | 0.0253 (6) | −0.0023 (5) | 0.0103 (5) | 0.0003 (5) |
C1 | 0.0268 (7) | 0.0356 (8) | 0.0475 (9) | −0.0008 (6) | 0.0129 (6) | −0.0004 (7) |
C2 | 0.0296 (9) | 0.0726 (14) | 0.0790 (15) | −0.0126 (9) | 0.0163 (9) | −0.0016 (12) |
C3 | 0.0305 (10) | 0.107 (2) | 0.0793 (17) | −0.0160 (11) | −0.0067 (10) | −0.0112 (15) |
C4 | 0.0437 (11) | 0.0867 (16) | 0.0464 (11) | 0.0005 (11) | −0.0106 (9) | −0.0070 (11) |
C5 | 0.0378 (9) | 0.0444 (9) | 0.0350 (8) | 0.0026 (7) | 0.0037 (7) | −0.0020 (7) |
C6 | 0.0350 (8) | 0.0394 (8) | 0.0444 (9) | −0.0021 (6) | 0.0232 (7) | 0.0029 (7) |
C7 | 0.0393 (8) | 0.0251 (7) | 0.0326 (7) | −0.0047 (6) | 0.0140 (6) | 0.0025 (6) |
C8 | 0.0373 (8) | 0.0274 (7) | 0.0247 (6) | 0.0020 (6) | 0.0065 (6) | 0.0028 (5) |
Ni1—O3 | 2.0879 (11) | C1—C6 | 1.504 (2) |
Ni1—O3i | 2.0879 (11) | C2—C3 | 1.383 (3) |
Ni1—N2 | 2.1116 (12) | C2—H2 | 0.9300 |
Ni1—N2i | 2.1117 (12) | C3—C4 | 1.382 (4) |
Ni1—N1i | 2.1253 (13) | C3—H3 | 0.9300 |
Ni1—N1 | 2.1253 (13) | C4—C5 | 1.380 (3) |
S1—O2 | 1.4424 (13) | C4—H4 | 0.9300 |
S1—O1 | 1.4547 (12) | C5—H5 | 0.9300 |
S1—O3 | 1.4753 (11) | C6—H6A | 0.9700 |
S1—C8 | 1.7860 (15) | C6—H6B | 0.9700 |
N1—C5 | 1.348 (2) | C7—C8 | 1.517 (2) |
N1—C1 | 1.349 (2) | C7—H7A | 0.9700 |
N2—C6 | 1.4849 (19) | C7—H7B | 0.9700 |
N2—C7 | 1.4911 (19) | C8—H8A | 0.9700 |
N2—H1N | 0.847 (18) | C8—H8B | 0.9700 |
C1—C2 | 1.387 (2) | ||
O3—Ni1—O3i | 180.0 | N1—C1—C6 | 115.17 (13) |
O3—Ni1—N2 | 92.95 (4) | C2—C1—C6 | 122.92 (16) |
O3i—Ni1—N2 | 87.05 (4) | C3—C2—C1 | 118.7 (2) |
O3—Ni1—N2i | 87.05 (4) | C3—C2—H2 | 120.7 |
O3i—Ni1—N2i | 92.95 (4) | C1—C2—H2 | 120.7 |
N2—Ni1—N2i | 180.00 (6) | C4—C3—C2 | 119.74 (19) |
O3—Ni1—N1i | 90.99 (5) | C4—C3—H3 | 120.1 |
O3i—Ni1—N1i | 89.01 (5) | C2—C3—H3 | 120.1 |
N2—Ni1—N1i | 100.96 (5) | C5—C4—C3 | 118.6 (2) |
N2i—Ni1—N1i | 79.04 (5) | C5—C4—H4 | 120.7 |
O3—Ni1—N1 | 89.01 (5) | C3—C4—H4 | 120.7 |
O3i—Ni1—N1 | 90.99 (5) | N1—C5—C4 | 122.30 (19) |
N2—Ni1—N1 | 79.04 (5) | N1—C5—H5 | 118.9 |
N2i—Ni1—N1 | 100.96 (5) | C4—C5—H5 | 118.9 |
N1i—Ni1—N1 | 180.0 | N2—C6—C1 | 109.17 (12) |
O2—S1—O1 | 113.76 (9) | N2—C6—H6A | 109.8 |
O2—S1—O3 | 112.97 (8) | C1—C6—H6A | 109.8 |
O1—S1—O3 | 110.02 (7) | N2—C6—H6B | 109.8 |
O2—S1—C8 | 107.25 (8) | C1—C6—H6B | 109.8 |
O1—S1—C8 | 105.88 (7) | H6A—C6—H6B | 108.3 |
O3—S1—C8 | 106.40 (7) | N2—C7—C8 | 111.68 (12) |
S1—O3—Ni1 | 129.73 (6) | N2—C7—H7A | 109.3 |
C5—N1—C1 | 118.73 (14) | C8—C7—H7A | 109.3 |
C5—N1—Ni1 | 127.92 (11) | N2—C7—H7B | 109.3 |
C1—N1—Ni1 | 113.01 (10) | C8—C7—H7B | 109.3 |
C6—N2—C7 | 109.81 (12) | H7A—C7—H7B | 107.9 |
C6—N2—Ni1 | 105.53 (9) | C7—C8—S1 | 112.62 (10) |
C7—N2—Ni1 | 116.81 (9) | C7—C8—H8A | 109.1 |
C6—N2—H1N | 105.4 (12) | S1—C8—H8A | 109.1 |
C7—N2—H1N | 106.7 (12) | C7—C8—H8B | 109.1 |
Ni1—N2—H1N | 112.0 (12) | S1—C8—H8B | 109.1 |
N1—C1—C2 | 121.91 (17) | H8A—C8—H8B | 107.8 |
O2—S1—O3—Ni1 | 101.05 (11) | N2i—Ni1—N2—C7 | 160 (17) |
O1—S1—O3—Ni1 | −130.63 (9) | N1i—Ni1—N2—C7 | 90.36 (11) |
C8—S1—O3—Ni1 | −16.37 (11) | N1—Ni1—N2—C7 | −89.64 (11) |
O3i—Ni1—O3—S1 | −153 (8) | C5—N1—C1—C2 | −1.3 (3) |
N2—Ni1—O3—S1 | 36.51 (10) | Ni1—N1—C1—C2 | 172.59 (15) |
N2i—Ni1—O3—S1 | −143.49 (10) | C5—N1—C1—C6 | 179.00 (14) |
N1i—Ni1—O3—S1 | −64.52 (10) | Ni1—N1—C1—C6 | −7.13 (17) |
N1—Ni1—O3—S1 | 115.48 (10) | N1—C1—C2—C3 | 0.7 (3) |
O3—Ni1—N1—C5 | 65.02 (14) | C6—C1—C2—C3 | −179.6 (2) |
O3i—Ni1—N1—C5 | −114.98 (14) | C1—C2—C3—C4 | 0.2 (4) |
N2—Ni1—N1—C5 | 158.22 (14) | C2—C3—C4—C5 | −0.6 (4) |
N2i—Ni1—N1—C5 | −21.78 (14) | C1—N1—C5—C4 | 0.9 (3) |
N1i—Ni1—N1—C5 | 76 (30) | Ni1—N1—C5—C4 | −171.96 (16) |
O3—Ni1—N1—C1 | −108.16 (11) | C3—C4—C5—N1 | 0.0 (4) |
O3i—Ni1—N1—C1 | 71.84 (11) | C7—N2—C6—C1 | 81.22 (15) |
N2—Ni1—N1—C1 | −14.97 (11) | Ni1—N2—C6—C1 | −45.48 (14) |
N2i—Ni1—N1—C1 | 165.03 (11) | N1—C1—C6—N2 | 36.05 (19) |
N1i—Ni1—N1—C1 | −97 (30) | C2—C1—C6—N2 | −143.67 (17) |
O3—Ni1—N2—C6 | 121.09 (10) | C6—N2—C7—C8 | −171.05 (12) |
O3i—Ni1—N2—C6 | −58.91 (10) | Ni1—N2—C7—C8 | −50.99 (15) |
N2i—Ni1—N2—C6 | −78 (17) | N2—C7—C8—S1 | 83.95 (13) |
N1i—Ni1—N2—C6 | −147.33 (9) | O2—S1—C8—C7 | −166.32 (11) |
N1—Ni1—N2—C6 | 32.67 (9) | O1—S1—C8—C7 | 71.88 (12) |
O3—Ni1—N2—C7 | −1.22 (10) | O3—S1—C8—C7 | −45.17 (12) |
O3i—Ni1—N2—C7 | 178.78 (10) |
Symmetry code: (i) −x, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N···O1ii | 0.847 (18) | 2.100 (19) | 2.9394 (17) | 170.6 (16) |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C8H11N2O3S)2] |
Mr | 489.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 9.609 (1), 9.927 (1), 11.4537 (12) |
β (°) | 106.848 (1) |
V (Å3) | 1045.66 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.17 |
Crystal size (mm) | 0.35 × 0.26 × 0.22 |
Data collection | |
Diffractometer | Bruker APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.683, 0.787 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8966, 2401, 2212 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.068, 1.04 |
No. of reflections | 2401 |
No. of parameters | 137 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.38 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N···O1i | 0.847 (18) | 2.100 (19) | 2.9394 (17) | 170.6 (16) |
Symmetry code: (i) x, −y+1/2, z−1/2. |
The compound is isostructural with [Co(C8H11N2O3S)2], whose structure has been described in detail (Li et al., 2006).The six-coordiante nickel atom lies on an inversion centre with the two monodeprotonated lingds coordinate in a tridentate facial arrangement with its three donor atoms.
The N—H donor and S?O acceptor groups of the PMT ligand participate in the hydrogen bonding and form a two-dimensional network in the bc plane (Fig. 2 and Table 2).