Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021174/bq2015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021174/bq2015Isup2.hkl |
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.011 Å
- R factor = 0.035
- wR factor = 0.123
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O4 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Sn1
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C6 -C11 1.36 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O1 .. 2.74 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Sn1 (2) 2.12
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For related literature, see: Allen et al. (1987); Bandoli et al. (1992, 1993); Barone et al. (2002); Hencher et al. (1982); Jiang & Ozin (1998); Nair & Nair (1991); Valiukonis et al. (1986).
Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Tin dioxide (30.1 mg, 0.2 mmol), 4-phenylpyridinium (62.8 mg, 0.4 mmol), nitric acid (0.2 mol/l, 4 ml) and ethanol (5 ml) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure for 7 d at 413 K and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature. Powder X-ray diffraction was conducted on the sample.
H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
In recent years, the researches on tin complexes draw increasing attention owning to their potential applications as photovoltaic materials, holographic recording system and biological activities (Jiang & Ozin, 1998; Valiukonis et al., 1986; Hencher et al., 1982; Bandoli et al., 1992, 1993), solar control devices (Nair & Nair, 1991) and semiconductor materials. Mononuclear or binuclear tin materials are important candidates as molecular precursors to prepare tin film materials by chemical vapor deposition (CVD)(Barone et al., 2002). 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 eight-coordinate environment of the Sn atom is completed by the eight O atoms of four NO3- (Table 1). The Sn—O bond lengths are in the range 2.466 (5) to 2.552 (5) Å. Hydrogen bonds
between C—H groups of free 4-phenylpyridinium and O atoms of neighboring molecules, with C···O distances of 3.032 (8) and 3.100 (8), generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure.
For related literature, see: Allen et al. (1987); Bandoli et al. (1992, 1993); Barone et al. (2002); Hencher et al. (1982); Jiang & Ozin (1998); Nair & Nair (1991); Valiukonis et al. (1986).
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.
(C11H9N)2[Sn(NO3)4] | F(000) = 1352 |
Mr = 677.11 | Dx = 1.784 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8235 reflections |
a = 20.121 (5) Å | θ = 2.5–29.5° |
b = 7.8112 (12) Å | µ = 1.09 mm−1 |
c = 18.307 (5) Å | T = 273 K |
β = 118.823 (9)° | Plane, colourless |
V = 2520.8 (10) Å3 | 0.40 × 0.33 × 0.21 mm |
Z = 4 |
Bruker APEXII area-detector diffractometer | 2495 independent reflections |
Radiation source: fine-focus sealed tube | 2450 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→25 |
Tmin = 0.656, Tmax = 0.801 | k = −9→9 |
8171 measured reflections | l = −22→22 |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0667P)2 + 16.0815P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2495 reflections | Δρmax = 0.88 e Å−3 |
187 parameters | Δρmin = −0.61 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0034 (4) |
(C11H9N)2[Sn(NO3)4] | V = 2520.8 (10) Å3 |
Mr = 677.11 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.121 (5) Å | µ = 1.09 mm−1 |
b = 7.8112 (12) Å | T = 273 K |
c = 18.307 (5) Å | 0.40 × 0.33 × 0.21 mm |
β = 118.823 (9)° |
Bruker APEXII area-detector diffractometer | 2495 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2450 reflections with I > 2σ(I) |
Tmin = 0.656, Tmax = 0.801 | Rint = 0.014 |
8171 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0667P)2 + 16.0815P] where P = (Fo2 + 2Fc2)/3 |
2495 reflections | Δρmax = 0.88 e Å−3 |
187 parameters | Δρmin = −0.61 e Å−3 |
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 | ||
Sn1 | 1.0000 | 0.33855 (4) | 0.7500 | 0.04796 (19) | |
O1 | 1.0921 (3) | 0.4420 (6) | 0.8900 (3) | 0.0671 (12) | |
O2 | 1.0826 (4) | 0.4129 (8) | 1.0028 (3) | 0.0948 (18) | |
O3 | 0.9970 (3) | 0.3046 (6) | 0.8849 (3) | 0.0675 (12) | |
O4 | 0.9294 (3) | 0.0724 (7) | 0.6688 (4) | 0.0773 (14) | |
O5 | 0.8183 (3) | −0.0046 (7) | 0.6531 (4) | 0.0850 (15) | |
O6 | 0.8782 (3) | 0.2146 (6) | 0.7289 (3) | 0.0673 (12) | |
N1 | 1.0582 (3) | 0.3864 (7) | 0.9290 (3) | 0.0609 (13) | |
N2 | 0.8730 (3) | 0.0901 (7) | 0.6818 (3) | 0.0572 (12) | |
N3 | 0.9363 (3) | 0.6016 (7) | 0.7803 (3) | 0.0571 (12) | |
C1 | 0.9745 (4) | 0.7370 (8) | 0.8257 (4) | 0.0579 (14) | |
H1 | 1.0235 | 0.7541 | 0.8343 | 0.069* | |
C2 | 0.9464 (4) | 0.8528 (7) | 0.8605 (4) | 0.0557 (14) | |
H2 | 0.9758 | 0.9452 | 0.8910 | 0.067* | |
C3 | 0.8639 (4) | 0.5857 (9) | 0.7678 (4) | 0.0625 (15) | |
H3 | 0.8347 | 0.4953 | 0.7349 | 0.075* | |
C4 | 0.8316 (4) | 0.6929 (8) | 0.8002 (4) | 0.0582 (14) | |
H4 | 0.7821 | 0.6751 | 0.7898 | 0.070* | |
C5 | 0.8742 (4) | 0.8307 (7) | 0.8497 (4) | 0.0509 (13) | |
C6 | 0.8427 (3) | 0.9443 (7) | 0.8910 (4) | 0.0511 (12) | |
C7 | 0.7945 (4) | 0.8780 (8) | 0.9188 (4) | 0.0560 (14) | |
H7 | 0.7821 | 0.7622 | 0.9127 | 0.067* | |
C8 | 0.7654 (4) | 0.9871 (9) | 0.9554 (4) | 0.0624 (15) | |
H8 | 0.7331 | 0.9433 | 0.9738 | 0.075* | |
C9 | 0.7820 (4) | 1.1524 (7) | 0.9653 (4) | 0.0508 (13) | |
H9 | 0.7616 | 1.2226 | 0.9905 | 0.061* | |
C10 | 0.8271 (5) | 1.2168 (10) | 0.9397 (6) | 0.078 (2) | |
H10 | 0.8371 | 1.3336 | 0.9460 | 0.093* | |
C11 | 0.8606 (5) | 1.1178 (9) | 0.9033 (5) | 0.0704 (19) | |
H11 | 0.8941 | 1.1661 | 0.8876 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0310 (3) | 0.0253 (2) | 0.0368 (3) | 0.000 | 0.02356 (19) | 0.000 |
O1 | 0.062 (3) | 0.070 (3) | 0.076 (3) | −0.012 (2) | 0.038 (2) | 0.001 (2) |
O2 | 0.123 (5) | 0.095 (4) | 0.052 (3) | −0.010 (4) | 0.031 (3) | −0.005 (3) |
O3 | 0.070 (3) | 0.073 (3) | 0.071 (3) | −0.017 (2) | 0.043 (2) | −0.005 (2) |
O4 | 0.082 (3) | 0.066 (3) | 0.104 (4) | −0.002 (3) | 0.060 (3) | −0.016 (3) |
O5 | 0.077 (3) | 0.076 (3) | 0.093 (4) | −0.033 (3) | 0.033 (3) | −0.018 (3) |
O6 | 0.074 (3) | 0.058 (2) | 0.084 (3) | −0.011 (2) | 0.051 (3) | −0.019 (2) |
N1 | 0.068 (3) | 0.057 (3) | 0.058 (3) | −0.001 (3) | 0.030 (3) | 0.002 (2) |
N2 | 0.061 (3) | 0.050 (3) | 0.063 (3) | −0.006 (2) | 0.032 (2) | −0.005 (2) |
N3 | 0.063 (3) | 0.056 (3) | 0.065 (3) | 0.001 (2) | 0.041 (3) | −0.003 (2) |
C1 | 0.062 (4) | 0.050 (3) | 0.076 (4) | −0.006 (3) | 0.046 (3) | −0.006 (3) |
C2 | 0.060 (4) | 0.051 (3) | 0.069 (4) | −0.007 (2) | 0.041 (3) | −0.007 (3) |
C3 | 0.059 (4) | 0.063 (4) | 0.068 (4) | −0.002 (3) | 0.033 (3) | −0.016 (3) |
C4 | 0.053 (3) | 0.062 (3) | 0.063 (3) | 0.000 (3) | 0.030 (3) | −0.012 (3) |
C5 | 0.056 (3) | 0.051 (3) | 0.055 (3) | 0.004 (2) | 0.034 (3) | 0.001 (2) |
C6 | 0.054 (3) | 0.051 (3) | 0.055 (3) | 0.002 (2) | 0.032 (3) | −0.002 (2) |
C7 | 0.058 (3) | 0.054 (3) | 0.066 (3) | −0.003 (3) | 0.038 (3) | −0.008 (3) |
C8 | 0.060 (4) | 0.073 (4) | 0.070 (4) | −0.002 (3) | 0.043 (3) | −0.005 (3) |
C9 | 0.056 (3) | 0.051 (3) | 0.061 (3) | 0.007 (2) | 0.040 (3) | −0.011 (2) |
C10 | 0.101 (6) | 0.053 (4) | 0.109 (6) | −0.005 (4) | 0.074 (5) | −0.015 (4) |
C11 | 0.093 (5) | 0.052 (3) | 0.100 (5) | −0.008 (3) | 0.073 (5) | −0.013 (3) |
Sn1—O1 | 2.466 (5) | C2—C5 | 1.379 (9) |
Sn1—O3 | 2.514 (5) | C2—H2 | 0.9300 |
Sn1—O4 | 2.552 (5) | C3—C4 | 1.359 (9) |
Sn1—O6 | 2.485 (5) | C3—H3 | 0.9300 |
Sn1—O1i | 2.466 (5) | C4—C5 | 1.402 (9) |
Sn1—O6i | 2.485 (5) | C4—H4 | 0.9300 |
Sn1—O3i | 2.514 (5) | C5—C6 | 1.490 (8) |
Sn1—O4i | 2.552 (5) | C6—C11 | 1.393 (9) |
O1—N1 | 1.278 (7) | C6—C7 | 1.395 (8) |
O2—N1 | 1.213 (7) | C7—C8 | 1.377 (8) |
O3—N1 | 1.271 (7) | C7—H7 | 0.9300 |
O4—N2 | 1.276 (7) | C8—C9 | 1.324 (9) |
O5—N2 | 1.215 (7) | C8—H8 | 0.9300 |
O6—N2 | 1.269 (7) | C9—C10 | 1.306 (10) |
N3—C1 | 1.336 (8) | C9—H9 | 0.9300 |
N3—C3 | 1.367 (8) | C10—C11 | 1.390 (9) |
C1—C2 | 1.374 (8) | C10—H10 | 0.9300 |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
O1—Sn1—O3 | 51.33 (15) | O5—N2—O4 | 123.7 (6) |
O1—Sn1—O4 | 143.24 (17) | O6—N2—O4 | 114.8 (5) |
O1—Sn1—O6 | 118.72 (15) | C1—N3—C3 | 115.0 (5) |
O3—Sn1—O4 | 102.50 (16) | N3—C1—C2 | 124.6 (6) |
O6—Sn1—O3 | 67.87 (16) | N3—C1—H1 | 117.7 |
O6—Sn1—O4 | 50.34 (15) | C2—C1—H1 | 117.7 |
O1i—Sn1—O6 | 77.00 (17) | C1—C2—C5 | 119.4 (6) |
O6i—Sn1—O6 | 134.1 (2) | C1—C2—H2 | 120.3 |
O1i—Sn1—O3 | 133.95 (16) | C5—C2—H2 | 120.3 |
O6i—Sn1—O3 | 107.13 (17) | C4—C3—N3 | 124.5 (6) |
O1—Sn1—O3i | 133.95 (16) | C4—C3—H3 | 117.8 |
O1i—Sn1—O3i | 51.33 (15) | N3—C3—H3 | 117.8 |
O6i—Sn1—O3i | 67.86 (16) | C3—C4—C5 | 118.9 (6) |
O6—Sn1—O3i | 107.13 (17) | C3—C4—H4 | 120.6 |
O3—Sn1—O3i | 167.9 (2) | C5—C4—H4 | 120.6 |
O1—Sn1—O4i | 74.51 (18) | C2—C5—C4 | 117.5 (5) |
O1i—Sn1—O4i | 143.24 (18) | C2—C5—C6 | 122.0 (5) |
O6i—Sn1—O4i | 50.34 (15) | C4—C5—C6 | 120.5 (6) |
O6—Sn1—O4i | 90.19 (17) | C11—C6—C7 | 118.3 (6) |
O3—Sn1—O4i | 67.15 (17) | C11—C6—C5 | 121.4 (5) |
O3i—Sn1—O4i | 102.50 (16) | C7—C6—C5 | 120.3 (5) |
O1i—Sn1—O4 | 74.51 (18) | C8—C7—C6 | 118.8 (6) |
O6i—Sn1—O4 | 90.19 (17) | C8—C7—H7 | 120.6 |
O1—Sn1—O1i | 141.7 (2) | C6—C7—H7 | 120.6 |
O1—Sn1—O6i | 77.00 (17) | C9—C8—C7 | 122.1 (6) |
O1i—Sn1—O6i | 118.72 (15) | C9—C8—H8 | 118.9 |
O3i—Sn1—O4 | 67.15 (17) | C7—C8—H8 | 118.9 |
O4i—Sn1—O4 | 70.9 (3) | C10—C9—C8 | 119.9 (6) |
N1—O1—Sn1 | 97.6 (4) | C10—C9—H9 | 120.0 |
N1—O3—Sn1 | 95.5 (3) | C8—C9—H9 | 120.0 |
N2—O4—Sn1 | 95.6 (3) | C9—C10—C11 | 122.7 (7) |
N2—O6—Sn1 | 99.1 (3) | C9—C10—H10 | 118.6 |
O2—N1—O3 | 122.7 (6) | C11—C10—H10 | 118.6 |
O2—N1—O1 | 121.7 (6) | C10—C11—C6 | 118.1 (6) |
O3—N1—O1 | 115.6 (5) | C10—C11—H11 | 120.9 |
O5—N2—O6 | 121.5 (6) | C6—C11—H11 | 120.9 |
Symmetry code: (i) −x+2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6 | 0.93 | 2.38 | 3.032 (8) | 127 |
C1—H1···O1 | 0.93 | 2.74 | 3.100 (8) | 104 |
Experimental details
Crystal data | |
Chemical formula | (C11H9N)2[Sn(NO3)4] |
Mr | 677.11 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 273 |
a, b, c (Å) | 20.121 (5), 7.8112 (12), 18.307 (5) |
β (°) | 118.823 (9) |
V (Å3) | 2520.8 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.09 |
Crystal size (mm) | 0.40 × 0.33 × 0.21 |
Data collection | |
Diffractometer | Bruker APEXII area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.656, 0.801 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8171, 2495, 2450 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.123, 1.02 |
No. of reflections | 2495 |
No. of parameters | 187 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0667P)2 + 16.0815P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.88, −0.61 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.
Sn1—O1 | 2.466 (5) | Sn1—O4 | 2.552 (5) |
Sn1—O3 | 2.514 (5) | Sn1—O6 | 2.485 (5) |
O1—Sn1—O3 | 51.33 (15) | O3—Sn1—O4 | 102.50 (16) |
O1—Sn1—O4 | 143.24 (17) | O6—Sn1—O3 | 67.87 (16) |
O1—Sn1—O6 | 118.72 (15) | O6—Sn1—O4 | 50.34 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O6 | 0.93 | 2.38 | 3.032 (8) | 127 |
C1—H1···O1 | 0.93 | 2.74 | 3.100 (8) | 104 |
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In recent years, the researches on tin complexes draw increasing attention owning to their potential applications as photovoltaic materials, holographic recording system and biological activities (Jiang & Ozin, 1998; Valiukonis et al., 1986; Hencher et al., 1982; Bandoli et al., 1992, 1993), solar control devices (Nair & Nair, 1991) and semiconductor materials. Mononuclear or binuclear tin materials are important candidates as molecular precursors to prepare tin film materials by chemical vapor deposition (CVD)(Barone et al., 2002). 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 eight-coordinate environment of the Sn atom is completed by the eight O atoms of four NO3- (Table 1). The Sn—O bond lengths are in the range 2.466 (5) to 2.552 (5) Å. Hydrogen bonds
between C—H groups of free 4-phenylpyridinium and O atoms of neighboring molecules, with C···O distances of 3.032 (8) and 3.100 (8), generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure.