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accesscatena-Poly[[(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)lead(II)]-di-μ-bromido]
aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my
In the title compound, [PbBr2(C14H12N2)]n, the PbII atom lies on a twofold rotation axis. The N-heterocycle-chelated PbII atom exists in a distorted octahedral geometry owing to two long Pb⋯Br interactions [2.9562 (5) and 3.2594 (5) Å]. These result in a zigzag chain running along the c axis. The lone pair is stereochemically inactive.
Related literature
For the lead(II) bromide–1,10-phenanthroline homolog, see: Bowmaker et al. (1996![[Bowmaker, G. A., Harrowfield, J. M., Miyamae, H., Shand, T. M., Skelton, B. W. & White, A. H. (1996). Aust. J. Chem. 49, 1089-1097.]](../../../../../../logos/arrows/e_arr.gif "Bowmaker, G. A., Harrowfield, J. M., Miyamae, H., Shand, T. M., Skelton, B. W. & White, A. H. (1996). Aust. J. Chem. 49, 1089-1097.")
).
![[Scheme 1]](bt5905scheme1.gif)
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
contains datablocks global, I. DOI: 10.1107/S160053681201940X/bt5905sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S160053681201940X/bt5905Isup2.hkl
Lead(II) bromide (0.37 g, 1 mmol) and 2,9-dimethyl-1,10-phenanthroline (1/5, 1 mmol) were loaded in a convection tube; the tube was filled with methanol and kept at 333 K. Colorless crystals were collected from the side arm after several days.
H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, Uiso(H) 1.2 to 1.5Ueq(C)] and were included in the in the riding model approximation.
The final difference Fourier map had a peak at 0.82 Å and a hole at 1.01 Å from Pb1.
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
![[Figure 1]](./bt5905fig1thm.gif) | Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of PbBr2(C14H12N2) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius; symmetry-related atoms are not labeled. Adjacent molecules are linked by a weak Pb···Br bond, which is denoted as a dashed line. |
| [PbBr2(C14H12N2)] | F(000) = 1048 |
| Mr = 575.27 | Dx = 2.546 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 2739 reflections |
| a = 18.3852 (13) Å | θ = 2.4–27.5° |
| b = 11.8312 (5) Å | µ = 16.55 mm−1 |
| c = 7.4609 (5) Å | T = 100 K |
| β = 112.346 (8)° | Prism, colorless |
| V = 1501.02 (16) Å3 | 0.15 × 0.15 × 0.05 mm |
| Z = 4 |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 1734 independent reflections |
| Radiation source: SuperNova (Mo) X-ray Source | 1620 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.032 |
| Detector resolution: 10.4041 pixels mm-1 | θmax = 27.6°, θmin = 2.4° |
| ω scan | h = −22→23 |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −15→11 |
| Tmin = 0.190, Tmax = 0.492 | l = −8→9 |
| 4947 measured reflections |
| 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 | H-atom parameters constrained |
| S = 1.01 | w = 1/[σ2(Fo2) + (0.0298P)2] where P = (Fo2 + 2Fc2)/3 |
| 1734 reflections | (Δ/σ)max = 0.001 |
| 88 parameters | Δρmax = 1.43 e Å−3 |
| 0 restraints | Δρmin = −1.45 e Å−3 |
| [PbBr2(C14H12N2)] | V = 1501.02 (16) Å3 |
| Mr = 575.27 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 18.3852 (13) Å | µ = 16.55 mm−1 |
| b = 11.8312 (5) Å | T = 100 K |
| c = 7.4609 (5) Å | 0.15 × 0.15 × 0.05 mm |
| β = 112.346 (8)° |
| Agilent SuperNova Dual diffractometer with an Atlas detector | 1734 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 1620 reflections with I > 2σ(I) |
| Tmin = 0.190, Tmax = 0.492 | Rint = 0.032 |
| 4947 measured reflections |
| R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
| wR(F2) = 0.058 | H-atom parameters constrained |
| S = 1.01 | Δρmax = 1.43 e Å−3 |
| 1734 reflections | Δρmin = −1.45 e Å−3 |
| 88 parameters |
| x | y | z | Uiso*/Ueq | ||
| Pb1 | 0.5000 | 0.399831 (16) | 0.2500 | 0.01318 (9) | |
| Br1 | 0.40287 (3) | 0.38883 (3) | 0.48715 (6) | 0.01909 (12) | |
| N1 | 0.5735 (2) | 0.2162 (3) | 0.3998 (5) | 0.0138 (7) | |
| C1 | 0.6822 (3) | 0.3265 (4) | 0.6184 (6) | 0.0261 (11) | |
| H1A | 0.6768 | 0.3765 | 0.5092 | 0.039* | |
| H1B | 0.7381 | 0.3151 | 0.6972 | 0.039* | |
| H1C | 0.6563 | 0.3610 | 0.6980 | 0.039* | |
| C2 | 0.6450 (3) | 0.2162 (4) | 0.5439 (6) | 0.0183 (9) | |
| C3 | 0.6839 (3) | 0.1139 (4) | 0.6216 (7) | 0.0241 (11) | |
| H3 | 0.7345 | 0.1152 | 0.7230 | 0.029* | |
| C4 | 0.6485 (3) | 0.0134 (4) | 0.5503 (6) | 0.0250 (11) | |
| H4 | 0.6743 | −0.0554 | 0.6030 | 0.030* | |
| C5 | 0.5748 (3) | 0.0111 (3) | 0.4008 (6) | 0.0206 (10) | |
| C6 | 0.5374 (3) | 0.1159 (3) | 0.3270 (6) | 0.0141 (9) | |
| C7 | 0.5352 (4) | −0.0932 (3) | 0.3218 (7) | 0.0257 (12) | |
| H7 | 0.5598 | −0.1631 | 0.3730 | 0.031* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Pb1 | 0.01465 (15) | 0.01085 (12) | 0.01436 (13) | 0.000 | 0.00588 (10) | 0.000 |
| Br1 | 0.0217 (3) | 0.0169 (2) | 0.0212 (2) | −0.00258 (17) | 0.0109 (2) | −0.00127 (15) |
| N1 | 0.014 (2) | 0.0143 (16) | 0.0136 (16) | 0.0002 (15) | 0.0052 (15) | −0.0005 (13) |
| C1 | 0.016 (3) | 0.035 (3) | 0.021 (2) | −0.004 (2) | 0.001 (2) | −0.0017 (19) |
| C2 | 0.016 (3) | 0.026 (2) | 0.0156 (19) | −0.0006 (19) | 0.0089 (19) | 0.0041 (17) |
| C3 | 0.014 (3) | 0.034 (3) | 0.023 (2) | 0.009 (2) | 0.005 (2) | 0.0105 (18) |
| C4 | 0.032 (3) | 0.024 (2) | 0.024 (2) | 0.013 (2) | 0.017 (2) | 0.0115 (19) |
| C5 | 0.028 (3) | 0.017 (2) | 0.024 (2) | 0.0061 (19) | 0.018 (2) | 0.0055 (17) |
| C6 | 0.020 (3) | 0.0131 (19) | 0.0137 (19) | 0.0009 (16) | 0.011 (2) | 0.0008 (14) |
| C7 | 0.045 (4) | 0.011 (2) | 0.032 (3) | 0.0033 (19) | 0.028 (3) | 0.0029 (16) |
| Pb1—N1i | 2.578 (3) | C2—C3 | 1.413 (6) |
| Pb1—N1 | 2.578 (3) | C3—C4 | 1.362 (7) |
| Pb1—Br1i | 2.9562 (5) | C3—H3 | 0.9500 |
| Pb1—Br1 | 2.9562 (5) | C4—C5 | 1.390 (7) |
| Pb1—Br1ii | 3.2594 (5) | C4—H4 | 0.9500 |
| N1—C2 | 1.345 (6) | C5—C6 | 1.423 (5) |
| N1—C6 | 1.368 (5) | C5—C7 | 1.440 (6) |
| C1—C2 | 1.481 (6) | C6—C6i | 1.417 (9) |
| C1—H1A | 0.9800 | C7—C7i | 1.330 (12) |
| C1—H1B | 0.9800 | C7—H7 | 0.9500 |
| C1—H1C | 0.9800 | ||
| N1i—Pb1—N1 | 65.15 (16) | N1—C2—C3 | 121.1 (4) |
| N1i—Pb1—Br1i | 92.27 (7) | N1—C2—C1 | 118.1 (4) |
| N1—Pb1—Br1i | 83.46 (7) | C3—C2—C1 | 120.8 (4) |
| N1i—Pb1—Br1 | 83.46 (7) | C4—C3—C2 | 119.6 (5) |
| N1—Pb1—Br1 | 92.27 (7) | C4—C3—H3 | 120.2 |
| Br1i—Pb1—Br1 | 174.955 (16) | C2—C3—H3 | 120.2 |
| N1i—Pb1—Br1ii | 169.82 (7) | C3—C4—C5 | 120.4 (4) |
| N1—Pb1—Br1ii | 107.98 (8) | C3—C4—H4 | 119.8 |
| Br1i—Pb1—Br1ii | 94.383 (13) | C5—C4—H4 | 119.8 |
| Br1—Pb1—Br1ii | 89.490 (13) | C4—C5—C6 | 118.3 (4) |
| C2—N1—C6 | 119.7 (4) | C4—C5—C7 | 122.1 (4) |
| C2—N1—Pb1 | 122.6 (3) | C6—C5—C7 | 119.6 (5) |
| C6—N1—Pb1 | 117.6 (3) | N1—C6—C6i | 119.8 (2) |
| C2—C1—H1A | 109.5 | N1—C6—C5 | 120.8 (4) |
| C2—C1—H1B | 109.5 | C6i—C6—C5 | 119.4 (3) |
| H1A—C1—H1B | 109.5 | C7i—C7—C5 | 121.0 (3) |
| C2—C1—H1C | 109.5 | C7i—C7—H7 | 119.5 |
| H1A—C1—H1C | 109.5 | C5—C7—H7 | 119.5 |
| H1B—C1—H1C | 109.5 | ||
| N1i—Pb1—N1—C2 | 179.5 (4) | C2—C3—C4—C5 | 0.5 (7) |
| Br1i—Pb1—N1—C2 | 83.9 (3) | C3—C4—C5—C6 | −0.8 (7) |
| Br1—Pb1—N1—C2 | −98.8 (3) | C3—C4—C5—C7 | −179.8 (4) |
| Br1ii—Pb1—N1—C2 | −8.6 (3) | C2—N1—C6—C6i | −179.0 (4) |
| N1i—Pb1—N1—C6 | −0.2 (2) | Pb1—N1—C6—C6i | 0.7 (6) |
| Br1i—Pb1—N1—C6 | −95.8 (3) | C2—N1—C6—C5 | −0.5 (6) |
| Br1—Pb1—N1—C6 | 81.5 (3) | Pb1—N1—C6—C5 | 179.2 (3) |
| Br1ii—Pb1—N1—C6 | 171.7 (3) | C4—C5—C6—N1 | 0.8 (6) |
| C6—N1—C2—C3 | 0.2 (6) | C7—C5—C6—N1 | 179.8 (4) |
| Pb1—N1—C2—C3 | −179.5 (3) | C4—C5—C6—C6i | 179.2 (5) |
| C6—N1—C2—C1 | 179.8 (4) | C7—C5—C6—C6i | −1.7 (7) |
| Pb1—N1—C2—C1 | 0.1 (5) | C4—C5—C7—C7i | −179.7 (5) |
| N1—C2—C3—C4 | −0.3 (7) | C6—C5—C7—C7i | 1.3 (8) |
| C1—C2—C3—C4 | −179.8 (4) |
| Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y+1, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | [PbBr2(C14H12N2)] |
| Mr | 575.27 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 18.3852 (13), 11.8312 (5), 7.4609 (5) |
| β (°) | 112.346 (8) |
| V (Å3) | 1501.02 (16) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 16.55 |
| Crystal size (mm) | 0.15 × 0.15 × 0.05 |
| Data collection | |
| Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
| Tmin, Tmax | 0.190, 0.492 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4947, 1734, 1620 |
| Rint | 0.032 |
| (sin θ/λ)max (Å−1) | 0.651 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.058, 1.01 |
| No. of reflections | 1734 |
| No. of parameters | 88 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 1.43, −1.45 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Acknowledgements
We thank Shahid Beheshti University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bowmaker, G. A., Harrowfield, J. M., Miyamae, H., Shand, T. M., Skelton, B. W. & White, A. H. (1996). Aust. J. Chem. 49, 1089–1097. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The N-heterocycle chelated PbII atom in PbBr2(C14H12N2) exists in a slightly distorted octahedral geometry with Pb···Br distances of 2.9562 (5)Å and 3.2594 (5)Å. The result are zigzag chains running along the c-axis of the monoclinic unit cell. The Pb centre lies on a twofold rotation axis. The lack of stereochemical activity can be attributed to crowding from the methyl substituents of the N-heterocycle (Bowmaker et al., 1996).