Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015884/cf6110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015884/cf6110Isup2.hkl |
CCDC reference: 175967
The title compound was crystallized from ethanol. It is a serendipitous hydrolysis product of a Schiff base palladium (II) complex.
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Fig. 1. View of (I) (70% probability displacement ellipsoids). | |
Fig. 2. Unit-cell packing diagram of (I) viewed along the b axis. |
C4H12Cl2N2Pd·0.5C2H6O | F(000) = 1144 |
Mr = 288.49 | Dx = 1.866 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I 2ya | Cell parameters from 3005 reflections |
a = 16.435 (5) Å | θ = 2–30.0° |
b = 7.562 (5) Å | µ = 2.27 mm−1 |
c = 16.527 (4) Å | T = 150 K |
β = 90.28 (2)° | Rectangular block, yellow-green |
V = 2053.9 (16) Å3 | 0.2 × 0.08 × 0.08 mm |
Z = 8 |
KappaCCD diffractometer | 2993 independent reflections |
Radiation source: Enraf Nonius FR590 | 2577 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
CCD rotation images, thick slices scans | θmax = 30.0°, θmin = 2.5° |
Absorption correction: multi-scan Blessing (1995) | h = −23→23 |
Tmin = 0.727, Tmax = 0.834 | k = −9→10 |
15940 measured reflections | l = −23→23 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | Only H-atom displacement parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0222P)2 + 4.1385P] where P = (Fo2 + 2Fc2)/3 |
2993 reflections | (Δ/σ)max = 0.002 |
123 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.64 e Å−3 |
C4H12Cl2N2Pd·0.5C2H6O | V = 2053.9 (16) Å3 |
Mr = 288.49 | Z = 8 |
Monoclinic, I2/a | Mo Kα radiation |
a = 16.435 (5) Å | µ = 2.27 mm−1 |
b = 7.562 (5) Å | T = 150 K |
c = 16.527 (4) Å | 0.2 × 0.08 × 0.08 mm |
β = 90.28 (2)° |
KappaCCD diffractometer | 2993 independent reflections |
Absorption correction: multi-scan Blessing (1995) | 2577 reflections with I > 2σ(I) |
Tmin = 0.727, Tmax = 0.834 | Rint = 0.045 |
15940 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.058 | Only H-atom displacement parameters refined |
S = 1.06 | Δρmax = 0.67 e Å−3 |
2993 reflections | Δρmin = −0.64 e Å−3 |
123 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. The disordered ethanol molecule was situated about a twofold axis. Its occupancy was fixed at 0.5 and hydrogen atoms were included in idealized positions with riding thermal parameters. The H-atoms in the complex were included in idealized positions with freely refined thermal parameters. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Pd | 0.750252 (10) | 0.07626 (2) | 0.182124 (9) | 0.02253 (6) | |
Cl2 | 0.84550 (4) | −0.06266 (8) | 0.26453 (4) | 0.03756 (15) | |
Cl1 | 0.84636 (4) | 0.17181 (10) | 0.09074 (3) | 0.03878 (16) | |
N1 | 0.66102 (11) | 0.1942 (3) | 0.11725 (10) | 0.0254 (4) | |
H12 | 0.6606 | 0.3134 | 0.1283 | 0.054 (10)* | |
H11 | 0.671 | 0.1799 | 0.0629 | 0.043 (8)* | |
N2 | 0.65645 (12) | 0.0038 (3) | 0.25503 (12) | 0.0313 (4) | |
H21 | 0.6488 | −0.1165 | 0.252 | 0.050 (9)* | |
H22 | 0.6686 | 0.0323 | 0.3078 | 0.054 (9)* | |
C1 | 0.57971 (13) | 0.1159 (3) | 0.13749 (13) | 0.0277 (5) | |
C10 | 0.51213 (15) | 0.2408 (4) | 0.10985 (16) | 0.0384 (6) | |
H10A | 0.4592 | 0.1913 | 0.125 | 0.045 (8)* | |
H10B | 0.5144 | 0.255 | 0.051 | 0.045 (8)* | |
H10C | 0.5193 | 0.3562 | 0.1359 | 0.046 (8)* | |
C11 | 0.57229 (16) | −0.0635 (4) | 0.09621 (15) | 0.0348 (6) | |
H11A | 0.6158 | −0.1415 | 0.1156 | 0.044 (8)* | |
H11B | 0.5769 | −0.0484 | 0.0375 | 0.037 (8)* | |
H11C | 0.5194 | −0.1159 | 0.109 | 0.045 (8)* | |
C2 | 0.58073 (14) | 0.0965 (4) | 0.22943 (14) | 0.0314 (5) | |
H2A | 0.5783 | 0.2147 | 0.255 | 0.026 (6)* | |
H2B | 0.5326 | 0.028 | 0.2471 | 0.037 (7)* | |
C100 | 0.7223 (7) | 0.8271 (17) | 0.4655 (6) | 0.045 (2) | 0.5 |
H10D | 0.727 | 0.7098 | 0.4394 | 0.054* | 0.5 |
H10E | 0.6693 | 0.8335 | 0.4936 | 0.054* | 0.5 |
C101 | 0.7912 (10) | 0.855 (3) | 0.5246 (12) | 0.125 (9) | 0.5 |
H10F | 0.7901 | 0.7622 | 0.5658 | 0.188* | 0.5 |
H10G | 0.7851 | 0.9709 | 0.5507 | 0.188* | 0.5 |
H10H | 0.8431 | 0.8512 | 0.4958 | 0.188* | 0.5 |
O100 | 0.7278 (6) | 0.9516 (12) | 0.4123 (4) | 0.129 (3) | 0.5 |
H100 | 0.6911 | 0.9389 | 0.3773 | 0.194* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd | 0.02233 (9) | 0.02410 (10) | 0.02112 (9) | −0.00189 (7) | −0.00549 (6) | 0.00008 (7) |
Cl2 | 0.0318 (3) | 0.0346 (3) | 0.0461 (4) | −0.0044 (2) | −0.0164 (3) | 0.0124 (3) |
Cl1 | 0.0278 (3) | 0.0636 (5) | 0.0249 (3) | −0.0062 (3) | −0.0020 (2) | 0.0043 (3) |
N1 | 0.0251 (9) | 0.0325 (11) | 0.0186 (8) | 0.0025 (8) | −0.0039 (7) | −0.0004 (8) |
N2 | 0.0284 (10) | 0.0413 (13) | 0.0240 (9) | −0.0087 (9) | −0.0066 (7) | 0.0051 (9) |
C1 | 0.0222 (10) | 0.0391 (14) | 0.0218 (10) | 0.0005 (9) | −0.0032 (8) | −0.0030 (9) |
C10 | 0.0298 (12) | 0.0522 (18) | 0.0330 (13) | 0.0123 (12) | −0.0062 (10) | −0.0060 (12) |
C11 | 0.0310 (12) | 0.0465 (16) | 0.0270 (12) | −0.0036 (11) | −0.0070 (9) | −0.0069 (11) |
C2 | 0.0262 (11) | 0.0461 (15) | 0.0219 (10) | −0.0039 (10) | −0.0010 (8) | −0.0038 (10) |
C100 | 0.042 (4) | 0.054 (5) | 0.038 (4) | −0.011 (3) | −0.022 (3) | 0.010 (3) |
C101 | 0.126 (13) | 0.115 (14) | 0.135 (14) | 0.010 (9) | 0.056 (10) | −0.059 (11) |
O100 | 0.172 (8) | 0.166 (8) | 0.049 (3) | −0.033 (6) | −0.035 (4) | 0.033 (4) |
Pd—N1 | 2.0197 (19) | C10—H10C | 0.98 |
Pd—N2 | 2.036 (2) | C11—H11A | 0.98 |
Pd—Cl1 | 2.3068 (8) | C11—H11B | 0.98 |
Pd—Cl2 | 2.3213 (9) | C11—H11C | 0.98 |
N1—C1 | 1.501 (3) | C2—H2A | 0.99 |
N1—H12 | 0.92 | C2—H2B | 0.99 |
N1—H11 | 0.92 | C100—O100 | 1.292 (14) |
N2—C2 | 1.488 (3) | C100—C101 | 1.506 (14) |
N2—H21 | 0.92 | C100—H10D | 0.99 |
N2—H22 | 0.92 | C100—H10E | 0.99 |
C1—C11 | 1.523 (4) | C101—H10F | 0.98 |
C1—C10 | 1.526 (3) | C101—H10G | 0.98 |
C1—C2 | 1.527 (3) | C101—H10H | 0.98 |
C10—H10A | 0.98 | O100—H100 | 0.84 |
C10—H10B | 0.98 | ||
N1—Pd—N2 | 83.28 (8) | H10A—C10—H10C | 109.5 |
N1—Pd—Cl1 | 90.69 (6) | H10B—C10—H10C | 109.5 |
N2—Pd—Cl1 | 173.96 (6) | C1—C11—H11A | 109.5 |
N1—Pd—Cl2 | 175.58 (5) | C1—C11—H11B | 109.5 |
N2—Pd—Cl2 | 92.38 (6) | H11A—C11—H11B | 109.5 |
Cl1—Pd—Cl2 | 93.66 (3) | C1—C11—H11C | 109.5 |
C1—N1—Pd | 110.66 (14) | H11A—C11—H11C | 109.5 |
C1—N1—H12 | 109.5 | H11B—C11—H11C | 109.5 |
Pd—N1—H12 | 109.5 | N2—C2—C1 | 109.49 (19) |
C1—N1—H11 | 109.5 | N2—C2—H2A | 109.8 |
Pd—N1—H11 | 109.5 | C1—C2—H2A | 109.8 |
H12—N1—H11 | 108.1 | N2—C2—H2B | 109.8 |
C2—N2—Pd | 109.86 (15) | C1—C2—H2B | 109.8 |
C2—N2—H21 | 109.7 | H2A—C2—H2B | 108.2 |
Pd—N2—H21 | 109.7 | O100—C100—C101 | 106.5 (13) |
C2—N2—H22 | 109.7 | O100—C100—H10D | 110.4 |
Pd—N2—H22 | 109.7 | C101—C100—H10D | 110.4 |
H21—N2—H22 | 108.2 | O100—C100—H10E | 110.4 |
N1—C1—C11 | 108.71 (19) | C101—C100—H10E | 110.4 |
N1—C1—C10 | 109.7 (2) | H10D—C100—H10E | 108.6 |
C11—C1—C10 | 111.1 (2) | C100—C101—H10F | 109.5 |
N1—C1—C2 | 104.73 (17) | C100—C101—H10G | 109.5 |
C11—C1—C2 | 111.1 (2) | H10F—C101—H10G | 109.5 |
C10—C1—C2 | 111.2 (2) | C100—C101—H10H | 109.5 |
C1—C10—H10A | 109.5 | H10F—C101—H10H | 109.5 |
C1—C10—H10B | 109.5 | H10G—C101—H10H | 109.5 |
H10A—C10—H10B | 109.5 | C100—O100—H100 | 109.5 |
C1—C10—H10C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···Cl2i | 0.92 | 2.59 | 3.405 (3) | 148 |
N1—H12···O100ii | 0.92 | 2.64 | 3.280 (9) | 127 |
N1—H11···Cl1iii | 0.92 | 2.55 | 3.443 (2) | 163 |
N2—H21···Cl2iv | 0.92 | 2.44 | 3.352 (3) | 170 |
N2—H22···O100v | 0.92 | 2.07 | 2.873 (6) | 145 |
N2—H22···Cl1i | 0.92 | 2.81 | 3.538 (3) | 137 |
O100—H100···N2vi | 0.84 | 2.15 | 2.873 (6) | 144 |
Symmetry codes: (i) −x+3/2, −y+1/2, −z+1/2; (ii) −x+3/2, −y+3/2, −z+1/2; (iii) −x+3/2, y, −z; (iv) −x+3/2, −y−1/2, −z+1/2; (v) x, y−1, z; (vi) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C4H12Cl2N2Pd·0.5C2H6O |
Mr | 288.49 |
Crystal system, space group | Monoclinic, I2/a |
Temperature (K) | 150 |
a, b, c (Å) | 16.435 (5), 7.562 (5), 16.527 (4) |
β (°) | 90.28 (2) |
V (Å3) | 2053.9 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.27 |
Crystal size (mm) | 0.2 × 0.08 × 0.08 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan Blessing (1995) |
Tmin, Tmax | 0.727, 0.834 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15940, 2993, 2577 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.058, 1.06 |
No. of reflections | 2993 |
No. of parameters | 123 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.67, −0.64 |
Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and WinGX (Farrugia, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).
Pd—N1 | 2.0197 (19) | N2—C2 | 1.488 (3) |
Pd—N2 | 2.036 (2) | C1—C11 | 1.523 (4) |
Pd—Cl1 | 2.3068 (8) | C1—C10 | 1.526 (3) |
Pd—Cl2 | 2.3213 (9) | C1—C2 | 1.527 (3) |
N1—C1 | 1.501 (3) | ||
N1—Pd—N2 | 83.28 (8) | N1—Pd—Cl2 | 175.58 (5) |
N1—Pd—Cl1 | 90.69 (6) | N2—Pd—Cl2 | 92.38 (6) |
N2—Pd—Cl1 | 173.96 (6) | Cl1—Pd—Cl2 | 93.66 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···Cl2i | 0.92 | 2.59 | 3.405 (3) | 148.2 |
N1—H12···O100ii | 0.92 | 2.64 | 3.280 (9) | 127.0 |
N1—H11···Cl1iii | 0.92 | 2.55 | 3.443 (2) | 162.5 |
N2—H21···Cl2iv | 0.92 | 2.44 | 3.352 (3) | 169.5 |
N2—H22···O100v | 0.92 | 2.07 | 2.873 (6) | 145.2 |
N2—H22···Cl1i | 0.92 | 2.81 | 3.538 (3) | 137.2 |
O100—H100···N2vi | 0.84 | 2.15 | 2.873 (6) | 143.7 |
Symmetry codes: (i) −x+3/2, −y+1/2, −z+1/2; (ii) −x+3/2, −y+3/2, −z+1/2; (iii) −x+3/2, y, −z; (iv) −x+3/2, −y−1/2, −z+1/2; (v) x, y−1, z; (vi) x, y+1, z. |
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