Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029832/lh2434sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029832/lh2434Isup2.hkl |
CCDC reference: 654805
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.031
- wR factor = 0.071
- Data-to-parameter ratio = 16.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.05 PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. S1 .. 2.98 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 3148 Count of symmetry unique reflns 1766 Completeness (_total/calc) 178.26% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1382 Fraction of Friedel pairs measured 0.783 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
(4-Chlorophenylsulfanyl)acetic acid was prepared by the nucleophilic reaction of chloroacetic acid and 4-chlorothiophenol under basic conditions. It was then oxidized using 30% aqueous hydrogen peroxide in acetic anhydride solution to produce 4-chlorophenylsulfinyl acetic acid (Nobles & Thompson, 1965). Nickel nitrate hexahydrate (0.592 g, 2 mmol), 4,4'-bipyridine (0.312 g, 2 mmol) and 4-chlorophenylsulfinyl acetic acid (0.437 g, 2 mmol) were dissolved in water and the pH was adjusted to 6 with 0.01 M sodium hydroxide; green crystals separated from the filtered solution after several days.
H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C) or C—H = 0.97 Å (methylene C), and with Uiso(H) = 1.2Ueq(C). Water H atoms were initially located in a difference Fourier map but they were treated as riding on their parent atoms with O—H = 0.85 Å and with Uiso(H) = 1.5Ueq(O).
The Flack parameter was refined from 1382 Friedel pairs.
Recently, we reported the crystal structures of diaquabis[(4-nitrophenylsulfinylacetato)(4,4'-bipyridine)zinc (Hou et al. 2007a), diaquabis[(4-chlorophenylsulfinylacetato)(4,4'-bipyridine)cobalt (Hou et al. 2007b) and diaquabis[(4-chlorophenylsulfinylacetato)(4,4'-bipyridine)zinc (Hou et al. 2007c); this paper reports the isostructural nickel compound.
In the title compound the nickel bis(4-chlorophenylsulfinylacetate) moiety is bridged by 4,4'-bipyridine into a linear chain (Fig. 1). The NiII atom shows an all trans octahedral coordination. The chains are connected into a three dimensional network via intermolecular O—H···O hydrogen bonds (Fig. 2).
For isostructural compounds, see: Hou, Yu et al. (2007a,b); Hou et al. (2007). For related literature, see: Nobles & Thompson (1965).
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.
[Ni(C8H6ClO3S)2(C10H8N2)(H2O)2] | F(000) = 2816 |
Mr = 686.20 | Dx = 1.554 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 13082 reflections |
a = 20.269 (4) Å | θ = 6.3–54.9° |
b = 25.503 (6) Å | µ = 1.04 mm−1 |
c = 11.345 (11) Å | T = 293 K |
V = 5865 (6) Å3 | Block, green |
Z = 8 | 0.36 × 0.34 × 0.06 mm |
Rigaku R-AXIS RAPID diffractometer | 3148 independent reflections |
Radiation source: fine-focus sealed tube | 2922 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −25→26 |
Tmin = 0.699, Tmax = 0.896 | k = −33→32 |
13880 measured reflections | l = −12→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0337P)2 + 3.8506P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
3148 reflections | Δρmax = 0.41 e Å−3 |
188 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1382 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.009 (12) |
[Ni(C8H6ClO3S)2(C10H8N2)(H2O)2] | V = 5865 (6) Å3 |
Mr = 686.20 | Z = 8 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 20.269 (4) Å | µ = 1.04 mm−1 |
b = 25.503 (6) Å | T = 293 K |
c = 11.345 (11) Å | 0.36 × 0.34 × 0.06 mm |
Rigaku R-AXIS RAPID diffractometer | 3148 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2922 reflections with I > 2σ(I) |
Tmin = 0.699, Tmax = 0.896 | Rint = 0.046 |
13880 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.071 | Δρmax = 0.41 e Å−3 |
S = 1.05 | Δρmin = −0.22 e Å−3 |
3148 reflections | Absolute structure: Flack (1983), 1382 Friedel pairs |
188 parameters | Absolute structure parameter: 0.009 (12) |
1 restraint |
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 | ||
C1 | 0.02738 (12) | 0.27432 (10) | 1.0801 (2) | 0.0288 (5) | |
C2 | 0.06467 (13) | 0.29286 (11) | 1.1730 (3) | 0.0384 (6) | |
H1 | 0.0610 | 0.2776 | 1.2471 | 0.046* | |
C3 | 0.10721 (14) | 0.33408 (11) | 1.1552 (3) | 0.0442 (7) | |
H2 | 0.1336 | 0.3463 | 1.2163 | 0.053* | |
C4 | 0.11011 (14) | 0.35688 (12) | 1.0454 (3) | 0.0467 (7) | |
C5 | 0.07312 (17) | 0.33870 (14) | 0.9523 (3) | 0.0515 (8) | |
H3 | 0.0761 | 0.3544 | 0.8785 | 0.062* | |
C6 | 0.03164 (16) | 0.29673 (13) | 0.9708 (3) | 0.0461 (7) | |
H4 | 0.0065 | 0.2836 | 0.9089 | 0.055* | |
C7 | 0.02904 (12) | 0.17011 (9) | 1.1228 (3) | 0.0347 (5) | |
H5 | 0.0568 | 0.1682 | 1.0532 | 0.042* | |
H6 | 0.0570 | 0.1775 | 1.1901 | 0.042* | |
C8 | −0.00613 (12) | 0.11761 (10) | 1.1409 (2) | 0.0310 (6) | |
C9 | 0.02268 (14) | −0.04086 (11) | 0.8755 (3) | 0.0384 (6) | |
H7 | 0.0395 | −0.0694 | 0.9168 | 0.046* | |
C10 | 0.02241 (16) | −0.04277 (12) | 0.7538 (3) | 0.0423 (7) | |
H8 | 0.0372 | −0.0726 | 0.7148 | 0.051* | |
C11 | 0.0000 | 0.0000 | 0.6903 (3) | 0.0301 (9) | |
C12 | 0.0000 | 0.0000 | 0.5593 (4) | 0.0353 (10) | |
C13 | 0.03408 (15) | 0.03756 (12) | 0.4951 (2) | 0.0391 (7) | |
H9 | 0.0571 | 0.0639 | 0.5339 | 0.047* | |
C14 | 0.03372 (13) | 0.03575 (11) | 0.3736 (3) | 0.0369 (6) | |
H10 | 0.0582 | 0.0607 | 0.3328 | 0.044* | |
Cl1 | 0.16225 (6) | 0.41043 (5) | 1.02446 (13) | 0.0889 (4) | |
N1 | 0.0000 | 0.0000 | 0.9364 (2) | 0.0260 (7) | |
N2 | 0.0000 | 0.0000 | 0.3110 (3) | 0.0307 (8) | |
Ni1 | 0.0000 | 0.0000 | 1.12362 (3) | 0.02230 (10) | |
O1 | −0.06260 (11) | 0.21128 (8) | 0.9883 (2) | 0.0528 (6) | |
O2 | −0.06426 (9) | 0.11872 (8) | 1.1772 (2) | 0.0493 (5) | |
O3 | 0.02798 (8) | 0.07784 (6) | 1.11784 (15) | 0.0296 (4) | |
O4 | 0.09886 (8) | −0.02184 (7) | 1.12220 (16) | 0.0332 (4) | |
H12 | 0.1000 | −0.0534 | 1.1464 | 0.050* | |
H11 | 0.1248 | −0.0079 | 1.1720 | 0.050* | |
S1 | −0.03045 (3) | 0.22185 (2) | 1.10534 (6) | 0.03402 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0316 (12) | 0.0244 (12) | 0.0304 (15) | 0.0017 (9) | −0.0044 (10) | 0.0017 (10) |
C2 | 0.0474 (15) | 0.0344 (15) | 0.0333 (14) | −0.0034 (12) | −0.0117 (12) | 0.0059 (12) |
C3 | 0.0444 (15) | 0.0378 (16) | 0.0503 (18) | −0.0059 (12) | −0.0150 (13) | −0.0006 (13) |
C4 | 0.0391 (14) | 0.0369 (16) | 0.064 (2) | −0.0068 (12) | 0.0044 (13) | 0.0072 (14) |
C5 | 0.063 (2) | 0.055 (2) | 0.0371 (17) | −0.0043 (16) | 0.0001 (14) | 0.0189 (15) |
C6 | 0.0570 (17) | 0.0492 (18) | 0.0322 (16) | −0.0065 (14) | −0.0107 (13) | 0.0028 (13) |
C7 | 0.0342 (11) | 0.0251 (12) | 0.0447 (16) | 0.0017 (9) | −0.0025 (12) | −0.0017 (11) |
C8 | 0.0391 (13) | 0.0285 (12) | 0.0256 (17) | −0.0012 (10) | −0.0007 (11) | −0.0022 (10) |
C9 | 0.0581 (16) | 0.0359 (14) | 0.0213 (14) | 0.0107 (12) | 0.0051 (12) | 0.0039 (11) |
C10 | 0.0677 (18) | 0.0350 (16) | 0.0242 (16) | 0.0131 (14) | 0.0077 (13) | −0.0003 (11) |
C11 | 0.037 (2) | 0.040 (3) | 0.013 (2) | −0.0003 (15) | 0.000 | 0.000 |
C12 | 0.046 (2) | 0.037 (3) | 0.022 (2) | 0.0065 (17) | 0.000 | 0.000 |
C13 | 0.0530 (16) | 0.0443 (18) | 0.0200 (14) | −0.0092 (13) | −0.0037 (12) | −0.0026 (12) |
C14 | 0.0452 (14) | 0.0401 (16) | 0.0255 (15) | −0.0097 (11) | 0.0001 (12) | 0.0037 (12) |
Cl1 | 0.0792 (6) | 0.0642 (7) | 0.1232 (11) | −0.0367 (5) | 0.0061 (7) | 0.0231 (7) |
N1 | 0.0327 (17) | 0.0333 (18) | 0.0121 (16) | −0.0014 (12) | 0.000 | 0.000 |
N2 | 0.0354 (18) | 0.0289 (19) | 0.028 (2) | 0.0015 (12) | 0.000 | 0.000 |
Ni1 | 0.03055 (18) | 0.02204 (19) | 0.01430 (17) | −0.00089 (18) | 0.000 | 0.000 |
O1 | 0.0502 (11) | 0.0421 (12) | 0.0660 (15) | −0.0015 (9) | −0.0291 (11) | −0.0030 (11) |
O2 | 0.0486 (11) | 0.0303 (10) | 0.0691 (15) | −0.0039 (9) | 0.0222 (10) | −0.0093 (10) |
O3 | 0.0389 (8) | 0.0236 (8) | 0.0265 (9) | −0.0012 (6) | 0.0005 (7) | −0.0003 (7) |
O4 | 0.0350 (8) | 0.0331 (9) | 0.0314 (9) | −0.0026 (7) | −0.0037 (8) | 0.0024 (9) |
S1 | 0.0320 (3) | 0.0254 (3) | 0.0446 (4) | 0.0018 (2) | −0.0021 (3) | −0.0017 (3) |
C1—C6 | 1.369 (4) | C10—H8 | 0.9300 |
C1—C2 | 1.380 (4) | C11—C10i | 1.384 (4) |
C1—S1 | 1.802 (3) | C11—C12 | 1.486 (4) |
C2—C3 | 1.375 (4) | C12—C13i | 1.388 (4) |
C2—H1 | 0.9300 | C12—C13 | 1.388 (4) |
C3—C4 | 1.375 (5) | C13—C14 | 1.378 (4) |
C3—H2 | 0.9300 | C13—H9 | 0.9300 |
C4—C5 | 1.376 (5) | C14—N2 | 1.343 (3) |
C4—Cl1 | 1.743 (3) | C14—H10 | 0.9300 |
C5—C6 | 1.377 (4) | N1—C9i | 1.332 (3) |
C5—H3 | 0.9300 | N1—Ni1 | 2.124 (3) |
C6—H4 | 0.9300 | N2—C14i | 1.343 (3) |
C7—C8 | 1.531 (3) | N2—Ni1ii | 2.125 (4) |
C7—S1 | 1.799 (2) | Ni1—O3i | 2.0657 (16) |
C7—H5 | 0.9700 | Ni1—O3 | 2.0657 (17) |
C7—H6 | 0.9700 | Ni1—O4 | 2.0799 (16) |
C8—O2 | 1.249 (3) | Ni1—O4i | 2.0799 (16) |
C8—O3 | 1.255 (3) | Ni1—N2iii | 2.125 (4) |
C9—N1 | 1.332 (3) | O1—S1 | 1.503 (2) |
C9—C10 | 1.381 (5) | O4—H12 | 0.8501 |
C9—H7 | 0.9300 | O4—H11 | 0.8500 |
C10—C11 | 1.384 (4) | ||
C6—C1—C2 | 120.9 (3) | C13i—C12—C11 | 121.7 (2) |
C6—C1—S1 | 119.7 (2) | C13—C12—C11 | 121.7 (2) |
C2—C1—S1 | 119.3 (2) | C14—C13—C12 | 119.9 (3) |
C3—C2—C1 | 119.6 (3) | C14—C13—H9 | 120.0 |
C3—C2—H1 | 120.2 | C12—C13—H9 | 120.0 |
C1—C2—H1 | 120.2 | N2—C14—C13 | 123.7 (3) |
C2—C3—C4 | 118.9 (3) | N2—C14—H10 | 118.2 |
C2—C3—H2 | 120.6 | C13—C14—H10 | 118.2 |
C4—C3—H2 | 120.6 | C9—N1—C9i | 117.5 (3) |
C3—C4—C5 | 122.0 (3) | C9—N1—Ni1 | 121.27 (17) |
C3—C4—Cl1 | 118.7 (3) | C9i—N1—Ni1 | 121.27 (17) |
C5—C4—Cl1 | 119.3 (3) | C14—N2—C14i | 116.1 (4) |
C4—C5—C6 | 118.5 (3) | C14—N2—Ni1ii | 121.96 (18) |
C4—C5—H3 | 120.7 | C14i—N2—Ni1ii | 121.96 (18) |
C6—C5—H3 | 120.7 | O3i—Ni1—O3 | 176.36 (10) |
C1—C6—C5 | 120.1 (3) | O3i—Ni1—O4 | 90.39 (7) |
C1—C6—H4 | 120.0 | O3—Ni1—O4 | 89.58 (7) |
C5—C6—H4 | 120.0 | O3i—Ni1—O4i | 89.58 (7) |
C8—C7—S1 | 110.14 (17) | O3—Ni1—O4i | 90.39 (7) |
C8—C7—H5 | 109.6 | O4—Ni1—O4i | 179.11 (10) |
S1—C7—H5 | 109.6 | O3i—Ni1—N1 | 88.18 (5) |
C8—C7—H6 | 109.6 | O3—Ni1—N1 | 88.18 (5) |
S1—C7—H6 | 109.6 | O4—Ni1—N1 | 89.56 (5) |
H5—C7—H6 | 108.1 | O4i—Ni1—N1 | 89.56 (5) |
O2—C8—O3 | 127.4 (2) | O3i—Ni1—N2iii | 91.82 (5) |
O2—C8—C7 | 117.6 (2) | O3—Ni1—N2iii | 91.82 (5) |
O3—C8—C7 | 115.0 (2) | O4—Ni1—N2iii | 90.44 (5) |
N1—C9—C10 | 123.0 (3) | O4i—Ni1—N2iii | 90.44 (5) |
N1—C9—H7 | 118.5 | N1—Ni1—N2iii | 180.000 (1) |
C10—C9—H7 | 118.5 | C8—O3—Ni1 | 128.23 (15) |
C9—C10—C11 | 119.6 (3) | Ni1—O4—H12 | 106.1 |
C9—C10—H8 | 120.2 | Ni1—O4—H11 | 118.7 |
C11—C10—H8 | 120.2 | H12—O4—H11 | 99.4 |
C10—C11—C10i | 117.3 (4) | O1—S1—C7 | 104.83 (13) |
C10—C11—C12 | 121.4 (2) | O1—S1—C1 | 105.96 (13) |
C10i—C11—C12 | 121.4 (2) | C7—S1—C1 | 97.25 (11) |
C13i—C12—C13 | 116.6 (4) |
Symmetry codes: (i) −x, −y, z; (ii) x, y, z−1; (iii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H11···S1iv | 0.85 | 2.98 | 3.822 (2) | 173 |
O4—H11···O1iv | 0.85 | 1.89 | 2.709 (3) | 160 |
O4—H12···O2i | 0.85 | 1.85 | 2.643 (3) | 154 |
Symmetry codes: (i) −x, −y, z; (iv) x+1/4, −y+1/4, z+1/4. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C8H6ClO3S)2(C10H8N2)(H2O)2] |
Mr | 686.20 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 293 |
a, b, c (Å) | 20.269 (4), 25.503 (6), 11.345 (11) |
V (Å3) | 5865 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.04 |
Crystal size (mm) | 0.36 × 0.34 × 0.06 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.699, 0.896 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13880, 3148, 2922 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.071, 1.05 |
No. of reflections | 3148 |
No. of parameters | 188 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.22 |
Absolute structure | Flack (1983), 1382 Friedel pairs |
Absolute structure parameter | 0.009 (12) |
Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H11···S1i | 0.85 | 2.98 | 3.822 (2) | 173.3 |
O4—H11···O1i | 0.85 | 1.89 | 2.709 (3) | 160.1 |
O4—H12···O2ii | 0.85 | 1.85 | 2.643 (3) | 154.4 |
Symmetry codes: (i) x+1/4, −y+1/4, z+1/4; (ii) −x, −y, z. |
Recently, we reported the crystal structures of diaquabis[(4-nitrophenylsulfinylacetato)(4,4'-bipyridine)zinc (Hou et al. 2007a), diaquabis[(4-chlorophenylsulfinylacetato)(4,4'-bipyridine)cobalt (Hou et al. 2007b) and diaquabis[(4-chlorophenylsulfinylacetato)(4,4'-bipyridine)zinc (Hou et al. 2007c); this paper reports the isostructural nickel compound.
In the title compound the nickel bis(4-chlorophenylsulfinylacetate) moiety is bridged by 4,4'-bipyridine into a linear chain (Fig. 1). The NiII atom shows an all trans octahedral coordination. The chains are connected into a three dimensional network via intermolecular O—H···O hydrogen bonds (Fig. 2).