Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031034/lh6312sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031034/lh6312Isup2.hkl |
CCDC reference: 262226
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (CCDC, 2002); software used to prepare material for publication: SHELXL97, TEXSAN (Molecular Structure Corporation, 2001), KENX (Sakai, 2002), ORTEPIII and Mercury.
(C8H10NO2)[Ni(C3S5)2] | Z = 2 |
Mr = 603.54 | F(000) = 610 |
Triclinic, P1 | ? # Insert any comments here. |
Hall symbol: -P 1 | Dx = 1.847 Mg m−3 |
a = 7.2051 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.139 (3) Å | Cell parameters from 2889 reflections |
c = 12.732 (3) Å | θ = 1.6–27.6° |
α = 84.319 (5)° | µ = 1.87 mm−1 |
β = 82.170 (5)° | T = 100 K |
γ = 80.583 (5)° | Plate, dark green |
V = 1085.0 (5) Å3 | 0.19 × 0.12 × 0.02 mm |
Bruker SMART APEX CCD area-detector diffractometer | 4870 independent reflections |
Radiation source: fine-focus sealed tube | 3426 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.6°, θmin = 1.6° |
ω scans | h = −9→9 |
Absorption correction: gaussian (XPREP in SAINT; Bruker, 2001) | k = −13→15 |
Tmin = 0.693, Tmax = 0.967 | l = −10→16 |
7209 measured reflections |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0961P)2] where P = (Fo2 + 2Fc2)/3 |
4870 reflections | (Δ/σ)max = 0.004 |
255 parameters | Δρmax = 1.68 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data. |
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. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.1123 (0.0022) x + 1.8207 (0.0054) y - 0.3058 (0.0090) z = 3.3400 (0.0091) * 0.0090 (0.0015) Ni1 * -0.0162 (0.0017) S6 * -0.0128 (0.0016) S7 * 0.0272 (0.0020) S8 * 0.0164 (0.0019) S9 * -0.0233 (0.0022) S10 * -0.0104 (0.0049) C4 * 0.0050 (0.0047) C5 * 0.0051 (0.0048) C6 Rms deviation of fitted atoms = 0.0157 6.8600 (0.0024) x + 3.2420 (0.0057) y - 1.8108 (0.0088) z = 2.9304 (0.0086) Angle to previous plane (with approximate e.s.d.) = 10.31 (0.04) * 0.1290 (0.0015) Ni1 * -0.0252 (0.0016) S1 * -0.0294 (0.0017) S2 * -0.0328 (0.0020) S3 * -0.0277 (0.0020) S4 * 0.0788 (0.0024) S5 * -0.0610 (0.0048) C1 * -0.0584 (0.0049) C2 * 0.0266 (0.0052) C3 Rms deviation of fitted atoms = 0.0615 |
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 | ||
S5 | 0.6474 (3) | 0.04139 (16) | 0.86499 (16) | 0.0390 (5) | |
Ni1 | 0.34409 (11) | 0.61546 (7) | 0.71595 (6) | 0.0162 (2) | |
S1 | 0.3720 (2) | 0.46387 (13) | 0.63556 (11) | 0.0173 (3) | |
S6 | 0.3119 (2) | 0.70143 (13) | 0.56141 (12) | 0.0216 (4) | |
S7 | 0.3048 (2) | 0.76996 (14) | 0.79397 (12) | 0.0215 (4) | |
S2 | 0.4032 (2) | 0.52568 (14) | 0.86671 (12) | 0.0221 (4) | |
S9 | 0.2430 (2) | 1.01230 (13) | 0.70363 (13) | 0.0246 (4) | |
S4 | 0.5349 (2) | 0.27808 (15) | 0.92125 (13) | 0.0249 (4) | |
S3 | 0.5045 (2) | 0.22199 (14) | 0.70851 (13) | 0.0236 (4) | |
S8 | 0.2515 (2) | 0.94934 (13) | 0.48965 (12) | 0.0221 (4) | |
S10 | 0.1843 (3) | 1.19043 (14) | 0.52853 (14) | 0.0295 (4) | |
O1 | −0.0299 (7) | 0.6507 (4) | 0.0176 (3) | 0.0262 (10) | |
C5 | 0.2772 (8) | 0.8698 (5) | 0.6883 (5) | 0.0161 (12) | |
N1 | 0.1408 (7) | 0.4012 (4) | 0.2470 (4) | 0.0206 (11) | |
C1 | 0.4404 (8) | 0.3625 (5) | 0.7327 (5) | 0.0171 (12) | |
O2 | −0.0323 (7) | 0.7798 (4) | 0.1319 (3) | 0.0282 (11) | |
C13 | −0.0074 (8) | 0.6765 (6) | 0.1032 (5) | 0.0225 (14) | |
C2 | 0.4546 (8) | 0.3890 (5) | 0.8325 (5) | 0.0196 (13) | |
C4 | 0.2786 (8) | 0.8393 (5) | 0.5882 (5) | 0.0165 (12) | |
C11 | 0.1752 (9) | 0.4299 (6) | 0.3405 (5) | 0.0242 (15) | |
H11 | 0.2191 | 0.3743 | 0.3907 | 0.029* | |
C12 | 0.1747 (10) | 0.2819 (6) | 0.2215 (5) | 0.0285 (15) | |
H12A | 0.3081 | 0.2584 | 0.2033 | 0.043* | |
H12B | 0.1089 | 0.2743 | 0.1625 | 0.043* | |
H12C | 0.1289 | 0.2361 | 0.2822 | 0.043* | |
C9 | 0.0857 (9) | 0.6232 (6) | 0.2882 (5) | 0.0234 (14) | |
H9 | 0.0657 | 0.6981 | 0.3030 | 0.028* | |
C6 | 0.2243 (9) | 1.0569 (5) | 0.5713 (5) | 0.0212 (13) | |
C14 | −0.0817 (11) | 0.8667 (6) | 0.0484 (5) | 0.0338 (17) | |
H14A | 0.0134 | 0.8589 | −0.0122 | 0.051* | |
H14B | −0.0886 | 0.9391 | 0.0743 | 0.051* | |
H14C | −0.2023 | 0.8594 | 0.0280 | 0.051* | |
C7 | 0.0818 (8) | 0.4821 (6) | 0.1706 (5) | 0.0235 (14) | |
H7 | 0.0604 | 0.4618 | 0.1053 | 0.028* | |
C3 | 0.5688 (9) | 0.1745 (6) | 0.8342 (5) | 0.0285 (16) | |
C8 | 0.0545 (8) | 0.5932 (6) | 0.1904 (5) | 0.0208 (13) | |
C10 | 0.1473 (9) | 0.5393 (5) | 0.3636 (4) | 0.0201 (13) | |
H10 | 0.1694 | 0.5575 | 0.4296 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S5 | 0.0537 (12) | 0.0209 (10) | 0.0402 (12) | 0.0003 (8) | −0.0123 (9) | 0.0077 (8) |
Ni1 | 0.0195 (4) | 0.0143 (4) | 0.0153 (4) | −0.0030 (3) | −0.0023 (3) | −0.0022 (3) |
S1 | 0.0240 (8) | 0.0136 (7) | 0.0149 (7) | −0.0025 (6) | −0.0038 (6) | −0.0018 (6) |
S6 | 0.0351 (9) | 0.0136 (8) | 0.0168 (8) | −0.0008 (6) | −0.0062 (6) | −0.0043 (6) |
S7 | 0.0301 (8) | 0.0199 (8) | 0.0150 (8) | −0.0052 (7) | −0.0018 (6) | −0.0028 (6) |
S2 | 0.0268 (8) | 0.0229 (9) | 0.0169 (8) | −0.0035 (6) | −0.0042 (6) | −0.0019 (6) |
S9 | 0.0400 (9) | 0.0146 (8) | 0.0197 (8) | −0.0053 (7) | −0.0011 (7) | −0.0054 (6) |
S4 | 0.0292 (9) | 0.0249 (9) | 0.0192 (8) | −0.0019 (7) | −0.0049 (6) | 0.0041 (7) |
S3 | 0.0323 (9) | 0.0145 (8) | 0.0238 (8) | −0.0027 (6) | −0.0047 (7) | −0.0002 (6) |
S8 | 0.0340 (9) | 0.0145 (8) | 0.0172 (8) | 0.0008 (6) | −0.0048 (6) | −0.0034 (6) |
S10 | 0.0471 (11) | 0.0142 (8) | 0.0264 (9) | −0.0014 (7) | −0.0058 (8) | −0.0019 (7) |
O1 | 0.039 (3) | 0.023 (3) | 0.017 (2) | −0.003 (2) | −0.0031 (19) | −0.0044 (19) |
C5 | 0.017 (3) | 0.014 (3) | 0.017 (3) | −0.004 (2) | 0.001 (2) | −0.003 (2) |
N1 | 0.019 (3) | 0.015 (3) | 0.030 (3) | −0.007 (2) | −0.001 (2) | −0.006 (2) |
C1 | 0.019 (3) | 0.016 (3) | 0.016 (3) | −0.005 (2) | −0.002 (2) | 0.001 (2) |
O2 | 0.045 (3) | 0.018 (2) | 0.022 (2) | −0.007 (2) | −0.002 (2) | −0.0036 (19) |
C13 | 0.018 (3) | 0.029 (4) | 0.020 (3) | −0.004 (3) | 0.007 (2) | −0.009 (3) |
C2 | 0.018 (3) | 0.023 (3) | 0.017 (3) | −0.003 (2) | −0.003 (2) | 0.003 (3) |
C4 | 0.021 (3) | 0.011 (3) | 0.016 (3) | −0.001 (2) | 0.001 (2) | −0.002 (2) |
C11 | 0.021 (3) | 0.028 (4) | 0.024 (3) | −0.007 (3) | −0.008 (3) | 0.010 (3) |
C12 | 0.031 (4) | 0.026 (4) | 0.031 (4) | −0.007 (3) | −0.011 (3) | 0.004 (3) |
C9 | 0.024 (3) | 0.026 (4) | 0.022 (3) | −0.008 (3) | 0.002 (3) | −0.009 (3) |
C6 | 0.024 (3) | 0.010 (3) | 0.030 (4) | −0.004 (2) | −0.003 (3) | −0.001 (3) |
C14 | 0.047 (4) | 0.027 (4) | 0.023 (4) | −0.001 (3) | 0.004 (3) | 0.003 (3) |
C7 | 0.018 (3) | 0.029 (4) | 0.025 (3) | −0.004 (3) | −0.006 (3) | −0.003 (3) |
C3 | 0.027 (3) | 0.030 (4) | 0.028 (4) | −0.007 (3) | −0.003 (3) | 0.009 (3) |
C8 | 0.019 (3) | 0.027 (4) | 0.017 (3) | −0.006 (3) | 0.001 (2) | −0.009 (3) |
C10 | 0.030 (3) | 0.026 (4) | 0.007 (3) | −0.008 (3) | −0.001 (2) | −0.009 (2) |
S5—C3 | 1.650 (7) | N1—C7 | 1.371 (8) |
Ni1—S6 | 2.1571 (17) | N1—C12 | 1.489 (8) |
Ni1—S1 | 2.1610 (18) | C1—C2 | 1.363 (8) |
Ni1—S7 | 2.1686 (19) | O2—C13 | 1.317 (8) |
Ni1—S2 | 2.1704 (17) | O2—C14 | 1.460 (8) |
S1—C1 | 1.718 (6) | C13—C8 | 1.489 (9) |
S6—C4 | 1.714 (6) | C11—C10 | 1.365 (9) |
S7—C5 | 1.729 (6) | C11—H11 | 0.9300 |
S2—C2 | 1.726 (7) | C12—H12A | 0.9600 |
S9—C5 | 1.733 (6) | C12—H12B | 0.9600 |
S9—C6 | 1.734 (6) | C12—H12C | 0.9600 |
S4—C3 | 1.724 (8) | C9—C8 | 1.388 (8) |
S4—C2 | 1.745 (6) | C9—C10 | 1.390 (9) |
S3—C1 | 1.739 (6) | C9—H9 | 0.9300 |
S3—C3 | 1.743 (7) | C14—H14A | 0.9600 |
S8—C6 | 1.719 (7) | C14—H14B | 0.9600 |
S8—C4 | 1.745 (6) | C14—H14C | 0.9600 |
S10—C6 | 1.649 (6) | C7—C8 | 1.374 (9) |
O1—C13 | 1.203 (7) | C7—H7 | 0.9300 |
C5—C4 | 1.360 (8) | C10—H10 | 0.9300 |
N1—C11 | 1.338 (8) | ||
S1···S6i | 3.667 (2) | S3···S9ii | 3.415 (2) |
S3···S6i | 3.600 (2) | S3···S10ii | 3.553 (2) |
S3···S8i | 3.524 (2) | S8···S8iii | 3.614 (3) |
S6—Ni1—S1 | 85.30 (7) | N1—C11—C10 | 121.4 (6) |
S6—Ni1—S7 | 93.31 (7) | N1—C11—H11 | 119.3 |
S1—Ni1—S7 | 177.60 (7) | C10—C11—H11 | 119.3 |
S6—Ni1—S2 | 174.91 (7) | N1—C12—H12A | 109.5 |
S1—Ni1—S2 | 93.47 (7) | N1—C12—H12B | 109.5 |
S7—Ni1—S2 | 88.09 (7) | H12A—C12—H12B | 109.5 |
C1—S1—Ni1 | 102.0 (2) | N1—C12—H12C | 109.5 |
C4—S6—Ni1 | 102.3 (2) | H12A—C12—H12C | 109.5 |
C5—S7—Ni1 | 101.9 (2) | H12B—C12—H12C | 109.5 |
C2—S2—Ni1 | 101.6 (2) | C8—C9—C10 | 118.7 (6) |
C5—S9—C6 | 96.8 (3) | C8—C9—H9 | 120.7 |
C3—S4—C2 | 97.0 (3) | C10—C9—H9 | 120.7 |
C1—S3—C3 | 96.8 (3) | S10—C6—S8 | 123.5 (4) |
C6—S8—C4 | 97.2 (3) | S10—C6—S9 | 122.8 (4) |
C4—C5—S7 | 120.9 (5) | S8—C6—S9 | 113.7 (3) |
C4—C5—S9 | 116.6 (4) | O2—C14—H14A | 109.5 |
S7—C5—S9 | 122.5 (4) | O2—C14—H14B | 109.5 |
C11—N1—C7 | 120.2 (6) | H14A—C14—H14B | 109.5 |
C11—N1—C12 | 121.1 (5) | O2—C14—H14C | 109.5 |
C7—N1—C12 | 118.6 (5) | H14A—C14—H14C | 109.5 |
C2—C1—S1 | 121.4 (5) | H14B—C14—H14C | 109.5 |
C2—C1—S3 | 116.2 (5) | N1—C7—C8 | 120.1 (6) |
S1—C1—S3 | 122.4 (4) | N1—C7—H7 | 119.9 |
C13—O2—C14 | 114.9 (5) | C8—C7—H7 | 119.9 |
O1—C13—O2 | 125.3 (6) | S5—C3—S4 | 124.5 (4) |
O1—C13—C8 | 123.0 (6) | S5—C3—S3 | 121.8 (5) |
O2—C13—C8 | 111.7 (5) | S4—C3—S3 | 113.7 (4) |
C1—C2—S2 | 121.3 (5) | C7—C8—C9 | 119.8 (6) |
C1—C2—S4 | 116.3 (5) | C7—C8—C13 | 117.1 (6) |
S2—C2—S4 | 122.4 (4) | C9—C8—C13 | 123.1 (6) |
C5—C4—S6 | 121.6 (4) | C11—C10—C9 | 119.8 (6) |
C5—C4—S8 | 115.6 (4) | C11—C10—H10 | 120.1 |
S6—C4—S8 | 122.7 (4) | C9—C10—H10 | 120.1 |
S6—Ni1—S1—C1 | 170.9 (2) | S7—C5—C4—S8 | −179.4 (3) |
S2—Ni1—S1—C1 | −4.1 (2) | S9—C5—C4—S8 | 1.6 (6) |
S1—Ni1—S6—C4 | 179.0 (2) | Ni1—S6—C4—C5 | −0.1 (5) |
S7—Ni1—S6—C4 | 1.0 (2) | Ni1—S6—C4—S8 | 177.9 (3) |
S6—Ni1—S7—C5 | −1.4 (2) | C6—S8—C4—C5 | −2.2 (5) |
S2—Ni1—S7—C5 | 173.7 (2) | C6—S8—C4—S6 | 179.7 (4) |
S1—Ni1—S2—C2 | 4.2 (2) | C7—N1—C11—C10 | 2.1 (9) |
S7—Ni1—S2—C2 | −177.6 (2) | C12—N1—C11—C10 | 178.9 (6) |
Ni1—S7—C5—C4 | 1.8 (5) | C4—S8—C6—S10 | −178.0 (4) |
Ni1—S7—C5—S9 | −179.2 (3) | C4—S8—C6—S9 | 2.1 (4) |
C6—S9—C5—C4 | −0.1 (5) | C5—S9—C6—S10 | 178.6 (4) |
C6—S9—C5—S7 | −179.1 (4) | C5—S9—C6—S8 | −1.4 (4) |
Ni1—S1—C1—C2 | 3.1 (5) | C11—N1—C7—C8 | −1.2 (9) |
Ni1—S1—C1—S3 | −174.2 (3) | C12—N1—C7—C8 | −178.1 (5) |
C3—S3—C1—C2 | −1.3 (5) | C2—S4—C3—S5 | 179.8 (4) |
C3—S3—C1—S1 | 176.1 (4) | C2—S4—C3—S3 | −2.1 (4) |
C14—O2—C13—O1 | −3.3 (9) | C1—S3—C3—S5 | −179.8 (4) |
C14—O2—C13—C8 | 176.4 (5) | C1—S3—C3—S4 | 2.1 (4) |
S1—C1—C2—S2 | 0.4 (7) | N1—C7—C8—C9 | −0.4 (9) |
S3—C1—C2—S2 | 177.9 (3) | N1—C7—C8—C13 | 179.3 (5) |
S1—C1—C2—S4 | −177.5 (3) | C10—C9—C8—C7 | 1.0 (9) |
S3—C1—C2—S4 | 0.0 (6) | C10—C9—C8—C13 | −178.6 (5) |
Ni1—S2—C2—C1 | −3.6 (5) | O1—C13—C8—C7 | −1.5 (9) |
Ni1—S2—C2—S4 | 174.1 (3) | O2—C13—C8—C7 | 178.8 (5) |
C3—S4—C2—C1 | 1.3 (5) | O1—C13—C8—C9 | 178.1 (6) |
C3—S4—C2—S2 | −176.5 (4) | O2—C13—C8—C9 | −1.5 (8) |
S7—C5—C4—S6 | −1.3 (7) | N1—C11—C10—C9 | −1.4 (9) |
S9—C5—C4—S6 | 179.7 (3) | C8—C9—C10—C11 | −0.2 (9) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1iv | 0.93 | 2.23 | 3.113 (8) | 158 |
Symmetry code: (iv) −x, −y+1, −z. |