Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056504/at2467sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056504/at2467Isup2.hkl |
CCDC reference: 1296844
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.123
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT362_ALERT_2_B Short C(sp3)-C(sp2) Bond C13 - C14 ... 1.22 Ang. PLAT411_ALERT_2_B Short Inter H...H Contact H5 .. H14B .. 2.00 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Desiraju (1995, 1997); Braga et al. (1998); Wu et al. (2003); Pan & Xu (2004); Liu et al. (2004); Li et al. (2005); Harrop et al. (2003); Qi, Ma et al. (2003); Qi, Qiu et al. (2003); Rauko et al. (2001); Foster et al. (1999); Zhou et al. (1999). 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, which was then sealed. Nickel (II) nitrate hexahydrate (290.8 mg, 1 mmol), phen (180.2 mg, 1 mmol), acetamide (59.1 mg, 1 mmol) and distilled water (8 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 N—H = 0.86 Å (for NH), 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,N), where x = 1.2 for aromatic and imino H atoms, and x = 1.5 for methyl H atoms.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Siemens, 1996).
[Ni(C2H4NO)(NO3)(C12H8N2)] | F(000) = 736 |
Mr = 358.99 | Dx = 1.799 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5602 reflections |
a = 8.7113 (11) Å | θ = 2.2–27.5° |
b = 9.2019 (14) Å | µ = 1.49 mm−1 |
c = 16.9102 (16) Å | T = 273 K |
β = 102.104 (6)° | Prism, green |
V = 1325.4 (3) Å3 | 0.40 × 0.25 × 0.20 mm |
Z = 4 |
Bruker APEXII area-detector diffractometer | 2653 independent reflections |
Radiation source: fine-focus sealed tube | 2273 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.584, Tmax = 0.751 | k = −11→11 |
8403 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0915P)2 + 0.5483P] where P = (Fo2 + 2Fc2)/3 |
2653 reflections | (Δ/σ)max < 0.001 |
209 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
[Ni(C2H4NO)(NO3)(C12H8N2)] | V = 1325.4 (3) Å3 |
Mr = 358.99 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7113 (11) Å | µ = 1.49 mm−1 |
b = 9.2019 (14) Å | T = 273 K |
c = 16.9102 (16) Å | 0.40 × 0.25 × 0.20 mm |
β = 102.104 (6)° |
Bruker APEXII area-detector diffractometer | 2653 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2273 reflections with I > 2σ(I) |
Tmin = 0.584, Tmax = 0.751 | Rint = 0.017 |
8403 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.72 e Å−3 |
2653 reflections | Δρmin = −0.61 e Å−3 |
209 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 | 0.66504 (4) | 0.92789 (4) | 0.803171 (18) | 0.03382 (16) | |
O1 | 0.5482 (3) | 1.0052 (3) | 0.70208 (12) | 0.0503 (5) | |
O2 | 0.3465 (3) | 0.9000 (4) | 0.72889 (18) | 0.0803 (9) | |
O3 | 0.3287 (3) | 1.0276 (3) | 0.62167 (16) | 0.0662 (7) | |
O4 | 0.6208 (2) | 0.5051 (2) | 0.74830 (14) | 0.0499 (5) | |
N1 | 0.6079 (3) | 1.0940 (3) | 0.86863 (15) | 0.0383 (5) | |
N2 | 0.7950 (3) | 0.8670 (3) | 0.90780 (13) | 0.0365 (5) | |
N3 | 0.6878 (3) | 0.7348 (2) | 0.75215 (12) | 0.0306 (4) | |
H3A | 0.7418 | 0.7239 | 0.7154 | 0.037* | |
N4 | 0.4024 (3) | 0.9773 (3) | 0.68400 (15) | 0.0432 (5) | |
C1 | 0.5205 (4) | 1.2104 (3) | 0.8465 (2) | 0.0473 (7) | |
H1 | 0.4819 | 1.2262 | 0.7916 | 0.057* | |
C2 | 0.4830 (4) | 1.3112 (4) | 0.9018 (2) | 0.0507 (7) | |
H2 | 0.4224 | 1.3926 | 0.8839 | 0.061* | |
C3 | 0.5365 (4) | 1.2877 (4) | 0.9809 (2) | 0.0507 (7) | |
H3 | 0.5101 | 1.3511 | 1.0188 | 0.061* | |
C4 | 0.6330 (3) | 1.1665 (3) | 1.00661 (18) | 0.0412 (6) | |
C5 | 0.6981 (4) | 1.1344 (4) | 1.08803 (18) | 0.0473 (7) | |
H5 | 0.6737 | 1.1926 | 1.1286 | 0.057* | |
C6 | 0.7960 (4) | 1.0193 (4) | 1.10811 (18) | 0.0471 (7) | |
H6 | 0.8382 | 1.0012 | 1.1624 | 0.057* | |
C7 | 0.8363 (4) | 0.9252 (3) | 1.04826 (18) | 0.0392 (6) | |
C8 | 0.9426 (4) | 0.8077 (3) | 1.06353 (18) | 0.0458 (7) | |
H8 | 0.9926 | 0.7861 | 1.1164 | 0.055* | |
C9 | 0.9724 (4) | 0.7260 (4) | 1.00158 (19) | 0.0475 (7) | |
H9 | 1.0437 | 0.6496 | 1.0116 | 0.057* | |
C10 | 0.8958 (4) | 0.7578 (3) | 0.92384 (19) | 0.0440 (7) | |
H10 | 0.9152 | 0.7011 | 0.8815 | 0.053* | |
C11 | 0.7672 (3) | 0.9512 (3) | 0.96844 (17) | 0.0342 (5) | |
C12 | 0.6655 (3) | 1.0728 (3) | 0.94748 (17) | 0.0345 (6) | |
C13 | 0.6164 (3) | 0.6283 (3) | 0.77801 (15) | 0.0318 (5) | |
C14 | 0.5451 (3) | 0.6523 (3) | 0.83137 (18) | 0.0402 (6) | |
H14A | 0.4509 | 0.5950 | 0.8223 | 0.060* | |
H14B | 0.5184 | 0.7535 | 0.8311 | 0.060* | |
H14C | 0.6099 | 0.6272 | 0.8828 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0402 (2) | 0.0328 (2) | 0.0268 (2) | 0.00247 (13) | 0.00345 (15) | 0.00109 (12) |
O1 | 0.0468 (11) | 0.0589 (15) | 0.0406 (11) | −0.0053 (10) | −0.0012 (9) | 0.0129 (10) |
O2 | 0.0612 (16) | 0.123 (3) | 0.0568 (16) | −0.0217 (16) | 0.0122 (13) | 0.0270 (17) |
O3 | 0.0586 (14) | 0.0730 (16) | 0.0565 (15) | −0.0050 (13) | −0.0119 (12) | 0.0174 (14) |
O4 | 0.0491 (12) | 0.0397 (12) | 0.0611 (13) | −0.0040 (9) | 0.0118 (10) | −0.0149 (10) |
N1 | 0.0407 (12) | 0.0358 (12) | 0.0381 (12) | 0.0003 (10) | 0.0076 (10) | 0.0046 (10) |
N2 | 0.0416 (11) | 0.0331 (11) | 0.0338 (11) | 0.0020 (10) | 0.0057 (9) | −0.0012 (9) |
N3 | 0.0389 (10) | 0.0301 (10) | 0.0241 (9) | −0.0035 (9) | 0.0094 (8) | −0.0030 (8) |
N4 | 0.0445 (13) | 0.0420 (13) | 0.0404 (12) | 0.0002 (11) | 0.0031 (11) | 0.0008 (11) |
C1 | 0.0482 (15) | 0.0421 (16) | 0.0492 (16) | 0.0060 (13) | 0.0048 (13) | 0.0042 (14) |
C2 | 0.0505 (16) | 0.0422 (16) | 0.0593 (19) | 0.0120 (13) | 0.0117 (14) | 0.0027 (14) |
C3 | 0.0517 (17) | 0.0417 (16) | 0.0623 (19) | 0.0074 (13) | 0.0206 (15) | −0.0058 (14) |
C4 | 0.0421 (14) | 0.0404 (14) | 0.0440 (14) | −0.0034 (12) | 0.0157 (12) | −0.0036 (12) |
C5 | 0.0546 (17) | 0.0525 (18) | 0.0384 (14) | −0.0026 (15) | 0.0182 (13) | −0.0088 (13) |
C6 | 0.0522 (16) | 0.0567 (18) | 0.0330 (14) | 0.0000 (15) | 0.0103 (13) | −0.0016 (13) |
C7 | 0.0439 (14) | 0.0406 (15) | 0.0330 (13) | −0.0042 (11) | 0.0079 (12) | 0.0025 (11) |
C8 | 0.0513 (16) | 0.0444 (16) | 0.0385 (14) | 0.0007 (13) | 0.0017 (12) | 0.0063 (13) |
C9 | 0.0517 (16) | 0.0387 (15) | 0.0479 (16) | 0.0088 (13) | 0.0008 (13) | 0.0038 (13) |
C10 | 0.0506 (15) | 0.0361 (14) | 0.0433 (15) | 0.0063 (12) | 0.0052 (13) | −0.0045 (12) |
C11 | 0.0375 (13) | 0.0319 (13) | 0.0334 (13) | −0.0029 (10) | 0.0076 (11) | 0.0008 (10) |
C12 | 0.0359 (13) | 0.0323 (13) | 0.0363 (13) | −0.0031 (10) | 0.0095 (11) | 0.0016 (10) |
C13 | 0.0319 (11) | 0.0303 (12) | 0.0312 (12) | 0.0021 (10) | 0.0020 (10) | −0.0028 (10) |
C14 | 0.0523 (15) | 0.0325 (13) | 0.0456 (14) | −0.0044 (12) | 0.0328 (13) | −0.0053 (11) |
Ni1—O1 | 1.933 (2) | C3—C4 | 1.409 (5) |
Ni1—O4i | 2.329 (2) | C3—H3 | 0.9300 |
Ni1—N1 | 2.010 (2) | C4—C12 | 1.394 (4) |
Ni1—N2 | 1.971 (2) | C4—C5 | 1.406 (4) |
Ni1—N3 | 2.003 (2) | C5—C6 | 1.357 (5) |
O1—N4 | 1.269 (3) | C5—H5 | 0.9300 |
O2—N4 | 1.214 (4) | C6—C7 | 1.431 (4) |
O3—N4 | 1.206 (4) | C6—H6 | 0.9300 |
O4—C13 | 1.244 (3) | C7—C11 | 1.378 (4) |
O4—Ni1ii | 2.329 (2) | C7—C8 | 1.412 (4) |
N1—C1 | 1.322 (4) | C8—C9 | 1.358 (5) |
N1—C12 | 1.337 (4) | C8—H8 | 0.9300 |
N2—C10 | 1.325 (4) | C9—C10 | 1.375 (4) |
N2—C11 | 1.346 (4) | C9—H9 | 0.9300 |
N3—C13 | 1.286 (4) | C10—H10 | 0.9300 |
N3—H3A | 0.8600 | C11—C12 | 1.426 (4) |
C1—C2 | 1.404 (5) | C13—C14 | 1.218 (4) |
C1—H1 | 0.9300 | C14—H14A | 0.9600 |
C2—C3 | 1.339 (5) | C14—H14B | 0.9600 |
C2—H2 | 0.9300 | C14—H14C | 0.9600 |
O1—Ni1—O4i | 82.63 (9) | C5—C4—C3 | 124.1 (3) |
O1—Ni1—N1 | 93.54 (10) | C6—C5—C4 | 120.8 (3) |
O1—Ni1—N2 | 174.49 (10) | C6—C5—H5 | 119.6 |
O1—Ni1—N3 | 91.54 (10) | C4—C5—H5 | 119.6 |
O4—Ni1—N1i | 138.78 (4) | C5—C6—C7 | 122.0 (3) |
O4—Ni1—N2i | 125.85 (4) | C5—C6—H6 | 119.0 |
O4—Ni1—N3i | 141.92 (5) | C7—C6—H6 | 119.0 |
N1—Ni1—N2 | 83.31 (10) | C11—C7—C8 | 116.5 (3) |
N1—Ni1—N3 | 165.94 (10) | C11—C7—C6 | 117.8 (3) |
N2—Ni1—N3 | 92.56 (9) | C8—C7—C6 | 125.7 (3) |
N4—O1—Ni1 | 116.96 (18) | C9—C8—C7 | 120.5 (3) |
C13—O4—Ni1ii | 121.59 (18) | C9—C8—H8 | 119.8 |
C1—N1—C12 | 118.3 (3) | C7—C8—H8 | 119.8 |
C1—N1—Ni1 | 130.9 (2) | C8—C9—C10 | 119.1 (3) |
C12—N1—Ni1 | 110.71 (18) | C8—C9—H9 | 120.4 |
C10—N2—C11 | 119.8 (2) | C10—C9—H9 | 120.4 |
C10—N2—Ni1 | 129.1 (2) | N2—C10—C9 | 121.7 (3) |
C11—N2—Ni1 | 111.07 (18) | N2—C10—H10 | 119.2 |
C13—N3—Ni1 | 115.54 (17) | C9—C10—H10 | 119.2 |
C13—N3—H3A | 122.2 | N2—C11—C7 | 122.3 (3) |
Ni1—N3—H3A | 122.2 | N2—C11—C12 | 117.6 (2) |
O3—N4—O2 | 124.1 (3) | C7—C11—C12 | 120.0 (3) |
O3—N4—O1 | 117.1 (3) | N1—C12—C4 | 122.4 (3) |
O2—N4—O1 | 118.7 (3) | N1—C12—C11 | 116.5 (2) |
N1—C1—C2 | 123.1 (3) | C4—C12—C11 | 121.1 (3) |
N1—C1—H1 | 118.4 | C14—C13—O4 | 121.9 (3) |
C2—C1—H1 | 118.4 | C14—C13—N3 | 118.1 (3) |
C3—C2—C1 | 118.6 (3) | O4—C13—N3 | 120.0 (2) |
C3—C2—H2 | 120.7 | C13—C14—H14A | 109.5 |
C1—C2—H2 | 120.7 | C13—C14—H14B | 109.5 |
C2—C3—C4 | 119.7 (3) | H14A—C14—H14B | 109.5 |
C2—C3—H3 | 120.1 | C13—C14—H14C | 109.5 |
C4—C3—H3 | 120.1 | H14A—C14—H14C | 109.5 |
C12—C4—C5 | 118.1 (3) | H14B—C14—H14C | 109.5 |
C12—C4—C3 | 117.8 (3) |
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 | 2.50 | 3.323 (4) | 148 |
C5—H5···O2iv | 0.93 | 2.60 | 3.215 (4) | 125 |
Symmetry codes: (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C2H4NO)(NO3)(C12H8N2)] |
Mr | 358.99 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 273 |
a, b, c (Å) | 8.7113 (11), 9.2019 (14), 16.9102 (16) |
β (°) | 102.104 (6) |
V (Å3) | 1325.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.49 |
Crystal size (mm) | 0.40 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.584, 0.751 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8403, 2653, 2273 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.123, 1.01 |
No. of reflections | 2653 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.72, −0.61 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
Ni1—O1 | 1.933 (2) | Ni1—N2 | 1.971 (2) |
Ni1—O4i | 2.329 (2) | Ni1—N3 | 2.003 (2) |
Ni1—N1 | 2.010 (2) | ||
O1—Ni1—O4i | 82.63 (9) | O4—Ni1—N2i | 125.85 (4) |
O1—Ni1—N1 | 93.54 (10) | O4—Ni1—N3i | 141.92 (5) |
O1—Ni1—N2 | 174.49 (10) | N1—Ni1—N2 | 83.31 (10) |
O1—Ni1—N3 | 91.54 (10) | N1—Ni1—N3 | 165.94 (10) |
O4—Ni1—N1i | 138.78 (4) | N2—Ni1—N3 | 92.56 (9) |
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 | 2.50 | 3.323 (4) | 148 |
C5—H5···O2iii | 0.93 | 2.60 | 3.215 (4) | 125 |
Symmetry codes: (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, −y+2, −z+2. |
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In the synthesis of crystal structures by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1995, 1997; Braga et al., 1998). Aromatic polycyclic compounds, such as phenanthroline, quinoline and benzimidazole, are one of the most important classes of biological ligands, the coordinations of metal-aromatic polycyclic compounds are of critical importance in biological systems, organic materials and coordination chemistry (Wu et al., 2003; Pan & Xu, 2004; Liu et al., 2004; Li et al., 2005). As a bidentate flexible ligand, acyl groups compounds are also a good ligand with excellent coordination capability to generate mono-, bi- or trinuclear complexes, which are commonly used as precursors for the formation of supramolecular architectures (Harrop et al., 2003; Qi, Ma et al., 2003; Qi, Qiu et al., 2003; Rauko et al., 2001; Foster et al., 1999; Zhou et al., 1999). We report herein the crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [Ni2(NO3)2(C2H4NO)2(C12H8N2)2]n, which are bridged by two bidentate acetamido groups with an inversion centre between the two NiII ions. Each Ni atom is five-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand, one O atom of NO3- and one N and one O atoms of acetamido ligands (Table 1). The Ni—O bond lengths are in the range 1.933 (2) to 2.329 (2) Å. The Ni—N bond lengths are in the range 1.971 (2) to 2.010 (2) Å.
In the crystal structure, no classic C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a polymeric ribbon structure.