Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058540/hk2379sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058540/hk2379Isup2.hkl |
CCDC reference: 1176499
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.040
- wR factor = 0.119
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT362_ALERT_2_B Short C(sp3)-C(sp2) Bond C13 - C14 ... 1.23 Ang. PLAT362_ALERT_2_B Short C(sp3)-C(sp2) Bond C15 - C16 ... 1.22 Ang. PLAT411_ALERT_2_B Short Inter H...H Contact H5 .. H14B .. 2.00 Ang. PLAT411_ALERT_2_B Short Inter H...H Contact H5 .. H16B .. 2.07 Ang.
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT410_ALERT_2_C Short Intra H...H Contact H14B .. H16B .. 1.93 Ang. PLAT413_ALERT_2_C Short Inter XH3 .. XHn H2 .. H14A .. 2.11 Ang.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For a related structure, see: Zhong et al. (2007). For bond-length data, see: Allen et al. (1987).
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Nickel (II) nitrate hexahydrate (295.6 mg, 1 mmol), phen (180.2 mg, 1 mmol), acetic acid (120.1 mg, 2 mmol), ammonia (4 ml, 0.5 mol/l) and distilled water (10 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small green crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.
The H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å, for aromatic and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H and x = 1.5 for methyl H atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
[Ni(C2H3O2)2(C12H8N2)] | F(000) = 736 |
Mr = 357.00 | Dx = 1.792 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2yn | Cell parameters from 5583 reflections |
a = 8.6901 (16) Å | θ = 2.3–27.2° |
b = 9.2108 (11) Å | µ = 1.49 mm−1 |
c = 16.9013 (12) Å | T = 273 K |
β = 102.009 (2)° | Prism, green |
V = 1323.2 (3) Å3 | 0.41 × 0.25 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2565 independent reflections |
Radiation source: fine-focus sealed tube | 2201 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 26.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.634, Tmax = 0.750 | k = −11→11 |
8148 measured reflections | l = −21→21 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0805P)2 + 1.1936P] where P = (Fo2 + 2Fc2)/3 |
2565 reflections | (Δ/σ)max = 0.001 |
210 parameters | Δρmax = 0.65 e Å−3 |
2 restraints | Δρmin = −0.46 e Å−3 |
[Ni(C2H3O2)2(C12H8N2)] | V = 1323.2 (3) Å3 |
Mr = 357.00 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.6901 (16) Å | µ = 1.49 mm−1 |
b = 9.2108 (11) Å | T = 273 K |
c = 16.9013 (12) Å | 0.41 × 0.25 × 0.20 mm |
β = 102.009 (2)° |
Bruker SMART CCD area-detector diffractometer | 2565 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2201 reflections with I > 2σ(I) |
Tmin = 0.634, Tmax = 0.750 | Rint = 0.017 |
8148 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 2 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.65 e Å−3 |
2565 reflections | Δρmin = −0.46 e Å−3 |
210 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 | 0.66500 (4) | 0.92790 (4) | 0.80317 (2) | 0.03410 (17) | |
O1 | 0.6879 (3) | 0.7349 (2) | 0.75205 (12) | 0.0429 (5) | |
O2 | 0.5482 (3) | 1.0050 (3) | 0.70200 (13) | 0.0513 (6) | |
O3 | 0.3284 (3) | 1.0286 (4) | 0.62163 (17) | 0.0680 (8) | |
O4 | 0.6213 (3) | 0.5048 (3) | 0.74825 (15) | 0.0504 (6) | |
N1 | 0.6078 (3) | 1.0936 (3) | 0.86839 (16) | 0.0389 (6) | |
N2 | 0.7958 (3) | 0.8672 (3) | 0.90797 (14) | 0.0374 (5) | |
C1 | 0.5196 (4) | 1.2113 (4) | 0.8470 (2) | 0.0470 (7) | |
H1 | 0.4802 | 1.2276 | 0.7922 | 0.056* | |
C2 | 0.4836 (4) | 1.3104 (4) | 0.9017 (2) | 0.0524 (8) | |
H2 | 0.4229 | 1.3916 | 0.8836 | 0.063* | |
C3 | 0.5369 (4) | 1.2885 (4) | 0.9811 (2) | 0.0504 (8) | |
H3 | 0.5113 | 1.3529 | 1.0188 | 0.060* | |
C4 | 0.6327 (4) | 1.1660 (4) | 1.00686 (19) | 0.0409 (7) | |
C5 | 0.6983 (4) | 1.1338 (4) | 1.0880 (2) | 0.0486 (8) | |
H5 | 0.6750 | 1.1926 | 1.1287 | 0.058* | |
C6 | 0.7948 (4) | 1.0185 (4) | 1.10778 (19) | 0.0474 (8) | |
H6 | 0.8355 | 0.9993 | 1.1621 | 0.057* | |
C7 | 0.8364 (4) | 0.9251 (3) | 1.04826 (19) | 0.0396 (7) | |
C8 | 0.9429 (4) | 0.8077 (4) | 1.06368 (19) | 0.0454 (7) | |
H8 | 0.9932 | 0.7865 | 1.1165 | 0.055* | |
C9 | 0.9724 (4) | 0.7257 (4) | 1.0018 (2) | 0.0478 (8) | |
H9 | 1.0433 | 0.6489 | 1.0118 | 0.057* | |
C10 | 0.8956 (4) | 0.7578 (4) | 0.92392 (19) | 0.0442 (7) | |
H10 | 0.9146 | 0.7009 | 0.8815 | 0.053* | |
C11 | 0.7674 (3) | 0.9513 (3) | 0.96839 (17) | 0.0346 (6) | |
C12 | 0.6652 (3) | 1.0726 (3) | 0.94744 (18) | 0.0345 (6) | |
C13 | 0.4031 (3) | 0.9781 (3) | 0.68378 (16) | 0.0338 (6) | |
C14 | 0.3459 (4) | 0.9000 (5) | 0.7292 (2) | 0.0539 (10) | |
H14A | 0.2383 | 0.9274 | 0.7266 | 0.081* | |
H14B | 0.4044 | 0.9112 | 0.7837 | 0.081* | |
H14C | 0.3502 | 0.8006 | 0.7128 | 0.081* | |
C15 | 0.6165 (3) | 0.6289 (3) | 0.77794 (17) | 0.0318 (6) | |
C16 | 0.5458 (4) | 0.6523 (3) | 0.83168 (19) | 0.0408 (7) | |
H16A | 0.4439 | 0.6077 | 0.8183 | 0.061* | |
H16B | 0.5341 | 0.7551 | 0.8376 | 0.061* | |
H16C | 0.6038 | 0.6125 | 0.8815 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0405 (2) | 0.0333 (2) | 0.0270 (2) | 0.00251 (14) | 0.00368 (16) | 0.00088 (13) |
O1 | 0.0530 (12) | 0.0407 (12) | 0.0356 (10) | −0.0038 (10) | 0.0102 (9) | −0.0024 (9) |
O2 | 0.0493 (13) | 0.0601 (16) | 0.0404 (12) | −0.0058 (11) | −0.0002 (10) | 0.0118 (11) |
O3 | 0.0587 (15) | 0.0760 (18) | 0.0595 (16) | −0.0063 (14) | −0.0102 (13) | 0.0185 (15) |
O4 | 0.0505 (13) | 0.0402 (13) | 0.0611 (14) | −0.0044 (10) | 0.0132 (11) | −0.0145 (11) |
N1 | 0.0410 (13) | 0.0357 (13) | 0.0397 (13) | 0.0024 (10) | 0.0077 (11) | 0.0044 (10) |
N2 | 0.0437 (13) | 0.0343 (13) | 0.0337 (12) | 0.0025 (11) | 0.0067 (10) | −0.0015 (10) |
C1 | 0.0494 (17) | 0.0427 (17) | 0.0473 (17) | 0.0057 (14) | 0.0067 (14) | 0.0059 (15) |
C2 | 0.0504 (18) | 0.0424 (18) | 0.064 (2) | 0.0127 (15) | 0.0110 (16) | 0.0045 (16) |
C3 | 0.0515 (18) | 0.0421 (18) | 0.061 (2) | 0.0077 (15) | 0.0201 (16) | −0.0044 (16) |
C4 | 0.0409 (15) | 0.0408 (16) | 0.0438 (15) | −0.0033 (13) | 0.0155 (13) | −0.0034 (13) |
C5 | 0.0562 (19) | 0.053 (2) | 0.0404 (16) | −0.0026 (16) | 0.0185 (15) | −0.0092 (15) |
C6 | 0.0526 (18) | 0.057 (2) | 0.0325 (15) | −0.0004 (16) | 0.0093 (14) | −0.0018 (14) |
C7 | 0.0442 (16) | 0.0404 (16) | 0.0340 (14) | −0.0041 (12) | 0.0076 (13) | 0.0027 (12) |
C8 | 0.0500 (17) | 0.0468 (18) | 0.0364 (15) | 0.0005 (14) | 0.0019 (13) | 0.0068 (13) |
C9 | 0.0511 (18) | 0.0390 (17) | 0.0498 (17) | 0.0088 (14) | 0.0023 (14) | 0.0032 (14) |
C10 | 0.0496 (17) | 0.0378 (16) | 0.0434 (16) | 0.0067 (13) | 0.0055 (14) | −0.0038 (13) |
C11 | 0.0388 (14) | 0.0322 (14) | 0.0332 (14) | −0.0040 (11) | 0.0087 (12) | −0.0006 (11) |
C12 | 0.0360 (14) | 0.0329 (14) | 0.0355 (14) | −0.0030 (11) | 0.0092 (12) | 0.0021 (11) |
C13 | 0.0340 (13) | 0.0343 (13) | 0.0300 (13) | 0.0001 (12) | −0.0005 (11) | −0.0001 (11) |
C14 | 0.0401 (16) | 0.088 (3) | 0.0335 (16) | −0.0182 (17) | 0.0074 (13) | 0.0195 (17) |
C15 | 0.0320 (12) | 0.0298 (13) | 0.0322 (13) | 0.0007 (11) | 0.0036 (11) | −0.0024 (11) |
C16 | 0.0542 (17) | 0.0318 (14) | 0.0473 (16) | −0.0047 (13) | 0.0355 (15) | −0.0054 (13) |
Ni1—O1 | 2.004 (2) | C4—C5 | 1.403 (5) |
Ni1—O2 | 1.933 (2) | C5—C6 | 1.352 (5) |
Ni1—O4i | 2.319 (2) | C5—H5 | 0.9300 |
Ni1—N1 | 2.005 (3) | C6—C7 | 1.426 (5) |
Ni1—N2 | 1.976 (2) | C6—H6 | 0.9300 |
O1—C15 | 1.282 (4) | C7—C11 | 1.379 (4) |
O2—C13 | 1.259 (4) | C7—C8 | 1.412 (5) |
O3—C13 | 1.207 (4) | C8—C9 | 1.357 (5) |
O4—C15 | 1.253 (4) | C8—H8 | 0.9300 |
O4—Ni1ii | 2.319 (2) | C9—C10 | 1.379 (5) |
N1—C1 | 1.333 (4) | C9—H9 | 0.9300 |
N1—C12 | 1.339 (4) | C10—H10 | 0.9300 |
N2—C10 | 1.320 (4) | C11—C12 | 1.426 (4) |
N2—C11 | 1.344 (4) | C13—C14 | 1.230 (4) |
C1—C2 | 1.381 (5) | C14—H14A | 0.9600 |
C1—H1 | 0.9300 | C14—H14B | 0.9600 |
C2—C3 | 1.341 (5) | C14—H14C | 0.9600 |
C2—H2 | 0.9300 | C15—C16 | 1.217 (4) |
C3—C4 | 1.416 (5) | C16—H16A | 0.9600 |
C3—H3 | 0.9300 | C16—H16B | 0.9600 |
C4—C12 | 1.395 (4) | C16—H16C | 0.9600 |
O1—Ni1—O2 | 91.46 (10) | C11—C7—C8 | 116.7 (3) |
O1—Ni1—O4i | 87.15 (9) | C11—C7—C6 | 117.6 (3) |
O2—Ni1—O4i | 82.54 (9) | C8—C7—C6 | 125.8 (3) |
O1—Ni1—N1 | 166.01 (10) | C9—C8—C7 | 120.4 (3) |
O1—Ni1—N2 | 92.61 (10) | C9—C8—H8 | 119.8 |
O2—Ni1—N1 | 93.55 (11) | C7—C8—H8 | 119.8 |
O2—Ni1—N2 | 174.38 (11) | C8—C9—C10 | 119.0 (3) |
O4—Ni1—N1i | 138.82 (4) | C8—C9—H9 | 120.5 |
O4—Ni1—N2i | 125.88 (5) | C10—C9—H9 | 120.5 |
N1—Ni1—N2 | 83.38 (10) | N2—C10—C9 | 121.7 (3) |
C15—O1—Ni1 | 115.48 (18) | N2—C10—H10 | 119.1 |
C13—O2—Ni1 | 117.3 (2) | C9—C10—H10 | 119.1 |
C15—O4—Ni1ii | 121.65 (19) | N2—C11—C7 | 122.1 (3) |
C1—N1—C12 | 117.5 (3) | N2—C11—C12 | 117.8 (3) |
C1—N1—Ni1 | 131.6 (2) | C7—C11—C12 | 120.1 (3) |
C12—N1—Ni1 | 110.76 (19) | N1—C12—C4 | 122.7 (3) |
C10—N2—C11 | 120.1 (3) | N1—C12—C11 | 116.4 (3) |
C10—N2—Ni1 | 129.0 (2) | C4—C12—C11 | 120.9 (3) |
C11—N2—Ni1 | 110.8 (2) | O3—C13—C14 | 123.7 (3) |
N1—C1—C2 | 123.6 (3) | O3—C13—O2 | 117.9 (3) |
N1—C1—H1 | 118.2 | C14—C13—O2 | 118.5 (3) |
C2—C1—H1 | 118.2 | C13—C14—H14A | 109.5 |
C3—C2—C1 | 119.5 (3) | C13—C14—H14B | 109.5 |
C3—C2—H2 | 120.3 | H14A—C14—H14B | 109.5 |
C1—C2—H2 | 120.3 | C13—C14—H14C | 109.5 |
C2—C3—C4 | 119.0 (3) | H14A—C14—H14C | 109.5 |
C2—C3—H3 | 120.5 | H14B—C14—H14C | 109.5 |
C4—C3—H3 | 120.5 | C16—C15—O4 | 121.6 (3) |
C12—C4—C5 | 118.1 (3) | C16—C15—O1 | 118.4 (3) |
C12—C4—C3 | 117.7 (3) | O4—C15—O1 | 120.0 (3) |
C5—C4—C3 | 124.2 (3) | C15—C16—H16A | 109.5 |
C6—C5—C4 | 120.8 (3) | C15—C16—H16B | 109.5 |
C6—C5—H5 | 119.6 | H16A—C16—H16B | 109.5 |
C4—C5—H5 | 119.6 | C15—C16—H16C | 109.5 |
C5—C6—C7 | 122.3 (3) | H16A—C16—H16C | 109.5 |
C5—C6—H6 | 118.8 | H16B—C16—H16C | 109.5 |
C7—C6—H6 | 118.8 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+3/2, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3iii | 0.93 | 2.51 | 3.332 (5) | 149 |
C10—H10···O2ii | 0.93 | 2.35 | 3.259 (4) | 163 |
Symmetry codes: (ii) −x+3/2, y−1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C2H3O2)2(C12H8N2)] |
Mr | 357.00 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 8.6901 (16), 9.2108 (11), 16.9013 (12) |
β (°) | 102.009 (2) |
V (Å3) | 1323.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.49 |
Crystal size (mm) | 0.41 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.634, 0.750 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8148, 2565, 2201 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.622 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.119, 0.99 |
No. of reflections | 2565 |
No. of parameters | 210 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.46 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
Ni1—O1 | 2.004 (2) | Ni1—N1 | 2.005 (3) |
Ni1—O2 | 1.933 (2) | Ni1—N2 | 1.976 (2) |
Ni1—O4i | 2.319 (2) | ||
O1—Ni1—O2 | 91.46 (10) | O2—Ni1—N1 | 93.55 (11) |
O1—Ni1—O4i | 87.15 (9) | O2—Ni1—N2 | 174.38 (11) |
O2—Ni1—O4i | 82.54 (9) | O4—Ni1—N1i | 138.82 (4) |
O1—Ni1—N1 | 166.01 (10) | O4—Ni1—N2i | 125.88 (5) |
O1—Ni1—N2 | 92.61 (10) | N1—Ni1—N2 | 83.38 (10) |
Symmetry code: (i) −x+3/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3ii | 0.93 | 2.51 | 3.332 (5) | 149 |
C10—H10···O2iii | 0.93 | 2.35 | 3.259 (4) | 163 |
Symmetry codes: (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+3/2, y−1/2, −z+3/2. |
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The crystal structure of catena-Poly[[(acetato-κO)(1,10-phenanthroline -κ2N,N')cobalt(II)]-µ-acetato-κ2O:O'], (II), has previously been reported (Zhong et al., 2007). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II). We report herein the crystal structure of (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). It is a polymeric complex involving bridging of NiII ions by single syn-anti acetate ligands. Each Ni atom is five-coordinated by two 1,10-phenanthroline (phen) N atoms and three O atoms of acetate ligands in a distorted square-pyramidal coordination geometry. The Ni—O and Ni—N bonds are in the range of [1.933 (2)–2.319 (2) Å] and [1.976 (2)–2.005 (3) Å], respectively (Table 1), as in (II).
In the crystal structure, C—H···O hydrogen bonds (Table 2, Fig. 2) result in the formation of a polymeric ribbon structure, as in (II).
The both compounds, (I) and (II), are isostructural.