Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112019075/gz3208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112019075/gz3208Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112019075/gz3208IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270112019075/gz3208IIIsup4.hkl |
CCDC references: 889369; 889370; 889371
For related literature, see: Batsanov (2001); Chae et al. (2001); Chuang et al. (2010); Dong et al. (2007); Fang et al. (2011); Fujita et al. (2007); Jiang et al. (2009); Masciocchi et al. (2009); Sarma, Jagarlapudi & Desiraju (1986); Wang et al. (2011); Yuan et al. (2011).
For the preparation of 1,2-bis[4-(pyridin-3-yl)phenoxy]ethane (L), sodium hydroxide (0.44 g, 11 mmol) was added with stirring to a solution of 1,2-bis(p-tolylsulfonyl)ethane (1.85 g, 5 mmol) and 4-(pyridin-3-yl)phenol (1.71 g, 10 mmol) in anhydrous N,N-dimethylformamide (50 ml). The mixture was stirred for 24 h at 358 K, and monitored by thin-layer chromatography (TLC). After removal of the solvent, the compound was purified by column chromatography using silica gel and CH2Cl2–MeOH (20:1 v/v) to afford L as a white crystalline solid (yield 1.54 g, 4.18 mmol, 83.7%). Elemental analysis calculated for C24H20N2O2: C 78.24, H 5.47, N 7.60%; found: C 78.17, H 5.38, N 7.73%.
For the preparation of (I), a solution of HgCl2(5.97 mg, 0.022 mmol) in methanol (8 ml) was layered onto a solution of L (8.10 mg, 0.022 mmol) in CH2Cl2 (8 ml). The system was left for about 1 week at room temperature and colourless crystals of (I) were obtained (yield 11.11 mg, 79%). IR (KBr pellet, cm-1): 3417(m), 3128 (m), 2925 (w), 2873 (w), 1605 (s), 1580 (w), 1515 (s), 1476 (s), 1452 (m), 1435 (m), 1399 (s), 1315 (w), 1282 (s), 1246 (s), 1200 (w), 1181 (s), 1131 (w), 1072 (m), 1026 (w), 1002 (w), 944 (m), 840 (m), 802 (s), 738 (w), 698 (m), 646 (w), 632 (m), 556 (m), 490 (w).
For the preparation of (II), a solution of HgBr2 (7.93 mg, 0.022 mmol) in methanol (8 ml) was layered onto a solution of L (8.10 mg, 0.022 mmol) in CH2Cl2 (8 ml). The system was left for about 1 week at room temperature and colourless crystals of (II) were obtained (yield 10.10 mg, 63%). IR (KBr pellet, cm-1): 3415 (m), 3128 (m), 2925 (w), 2873 (w), 1605 (s), 1516 (s), 1476 (s), 1452 (m), 1436 (m), 1400 (s), 1282 (s), 1246 (s), 1181 (s), 1130 (w), 1072 (m), 1026 (w), 1001 (w), 944 (m), 837 (m), 802 (s), 738 (w), 698 (m), 646 (w), 632( m), 555 (m).
For the preparation of (III), a solution of HgI2 (10.00 mg, 0.022 mmol) in methanol (7 ml) was layered onto a solution of L (8.10 mg, 0.022 mmol) in CH2Cl2 (7 ml). The system was left for about 1 week at room temperature and colourless crystals of (III) were obtained (yield 10.67 mg, 59%). IR (KBr pellet, cm-1): 3417 (m), 3128 (m), 2919 (w), 1605 (s), 1517 (s), 1475 (s), 1450 (m), 1436 (m), 1399 (s), 1313 (w), 1280 (s), 1246 (s), 1180 (s), 1130 (w), 1073 (m), 1024 (w), 1001 (w), 950 (s), 836 (s), 801 (s), 738 (w), 700 (m), 646 (w), 630 (m), 553 (m).
H atoms were placed in geometrically idealized positions and included as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) (aromatic) and C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) (methylene). Atoms O1, O2, C12 and C13 in (I) are statistically disordered because of the rotation about the C—O bond, Attempts to model the disorder were not successful. The ratio of the disorder part is less than 20%; the minor component is not included in the refinement. In the C6–C11 benzene ring of (III), the bond lengths except for the C6—C11 bond range from 1.358 to 1.378 Å; a restraint of 1.37 (1) Å was applied to the longer C6—C11 bond to keep the rationality of the ring. As a result, the C6—C11 bond length is 1.388 Å.
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Hg2Cl4(C24H20N2O2)2] | Z = 1 |
Mr = 1279.82 | F(000) = 616 |
Triclinic, P1 | Dx = 1.927 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7822 (15) Å | Cell parameters from 3326 reflections |
b = 10.6904 (18) Å | θ = 2.4–26.0° |
c = 12.044 (2) Å | µ = 7.25 mm−1 |
α = 86.662 (2)° | T = 298 K |
β = 78.930 (2)° | Block, colourless |
γ = 84.014 (2)° | 0.20 × 0.15 × 0.15 mm |
V = 1102.8 (3) Å3 |
Bruker SMART CCD area-detector diffractometer | 4066 independent reflections |
Radiation source: fine-focus sealed tube | 3708 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ϕand ω scans | θmax = 25.6°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.325, Tmax = 0.410 | k = −9→12 |
5867 measured reflections | l = −14→10 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0783P)2 + 0.1498P] where P = (Fo2 + 2Fc2)/3 |
4066 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 1.99 e Å−3 |
0 restraints | Δρmin = −1.68 e Å−3 |
[Hg2Cl4(C24H20N2O2)2] | γ = 84.014 (2)° |
Mr = 1279.82 | V = 1102.8 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.7822 (15) Å | Mo Kα radiation |
b = 10.6904 (18) Å | µ = 7.25 mm−1 |
c = 12.044 (2) Å | T = 298 K |
α = 86.662 (2)° | 0.20 × 0.15 × 0.15 mm |
β = 78.930 (2)° |
Bruker SMART CCD area-detector diffractometer | 4066 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3708 reflections with I > 2σ(I) |
Tmin = 0.325, Tmax = 0.410 | Rint = 0.021 |
5867 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.99 e Å−3 |
4066 reflections | Δρmin = −1.68 e Å−3 |
280 parameters |
Experimental. Spectroscopic data for (I): IR (KBr pellet, cm-1): 3453 (s), 2948 (w), 2931 (w), 1635 (s), 1610 (s), 1517 (s), 1474 (s), 1454 (s), 1428 (w), 1384 (s), 1338 (w), 1311 (w), 1283 (m), 1243 (s), 1180 (m), 1116 (w), 1102 (w), 1079 (s), 1069 (s), 997 (m), 938 (m), 841 (s), 801 (s), 713 (s), 629 (s), 554 (m), 512 (w); 1H NMR (300 MHz, DMSO, 25°, TMS): δ 8.85 (s, 1H, -C5H4N), 8.51 (d, 1H, -C5H4N), 8.03 (d, 1H, -C5H4N), 7.46 (t, 1H, -C5H4N), 7.46-7.11 (aabb, 4H, -C6H4-), 4.40 (s, 2H, -CH2-). |
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 | ||
C1 | 0.5273 (11) | −0.4072 (9) | 0.7328 (7) | 0.066 (2) | |
H1 | 0.4942 | −0.4835 | 0.7643 | 0.080* | |
C2 | 0.6001 (12) | −0.4014 (9) | 0.6195 (7) | 0.073 (2) | |
H2 | 0.6212 | −0.4736 | 0.5775 | 0.087* | |
C3 | 0.6396 (10) | −0.2886 (8) | 0.5718 (6) | 0.059 (2) | |
H3 | 0.6825 | −0.2827 | 0.4951 | 0.071* | |
C4 | 0.6170 (7) | −0.1811 (7) | 0.6356 (6) | 0.0447 (15) | |
C5 | 0.5488 (8) | −0.2015 (7) | 0.7505 (6) | 0.0464 (16) | |
H5 | 0.5350 | −0.1330 | 0.7969 | 0.056* | |
C6 | 0.6608 (7) | −0.0570 (7) | 0.5892 (5) | 0.0434 (15) | |
C7 | 0.7768 (9) | −0.0447 (7) | 0.4944 (6) | 0.0544 (18) | |
H7 | 0.8263 | −0.1170 | 0.4590 | 0.065* | |
C8 | 0.8210 (9) | 0.0695 (8) | 0.4512 (6) | 0.0559 (19) | |
H8 | 0.8995 | 0.0736 | 0.3874 | 0.067* | |
C9 | 0.7507 (9) | 0.1790 (7) | 0.5010 (6) | 0.0498 (16) | |
C10 | 0.6316 (9) | 0.1695 (7) | 0.5935 (6) | 0.0565 (19) | |
H10 | 0.5803 | 0.2422 | 0.6270 | 0.068* | |
C11 | 0.5879 (9) | 0.0545 (7) | 0.6368 (6) | 0.0518 (17) | |
H11 | 0.5077 | 0.0508 | 0.6994 | 0.062* | |
C12 | 0.9080 (14) | 0.3037 (9) | 0.3653 (8) | 0.087 (3) | |
H12A | 0.8650 | 0.2888 | 0.2994 | 0.105* | |
H12B | 0.9932 | 0.2394 | 0.3703 | 0.105* | |
C13 | 0.9697 (13) | 0.4351 (13) | 0.3523 (11) | 0.096 (3) | |
H13A | 0.9947 | 0.4580 | 0.4231 | 0.115* | |
H13B | 1.0629 | 0.4355 | 0.2941 | 0.115* | |
C14 | 0.8966 (10) | 0.6362 (8) | 0.2860 (7) | 0.058 (2) | |
C15 | 1.0303 (10) | 0.6899 (9) | 0.2961 (7) | 0.066 (2) | |
H15 | 1.1053 | 0.6450 | 0.3317 | 0.079* | |
C16 | 1.0509 (8) | 0.8119 (8) | 0.2524 (7) | 0.0565 (19) | |
H16 | 1.1410 | 0.8470 | 0.2594 | 0.068* | |
C17 | 0.9437 (7) | 0.8829 (6) | 0.1992 (5) | 0.0394 (14) | |
C18 | 0.8096 (8) | 0.8235 (7) | 0.1906 (6) | 0.0479 (16) | |
H18 | 0.7342 | 0.8674 | 0.1549 | 0.057* | |
C19 | 0.7872 (9) | 0.7043 (8) | 0.2330 (7) | 0.0557 (18) | |
H19 | 0.6974 | 0.6688 | 0.2260 | 0.067* | |
C20 | 0.9645 (7) | 1.0120 (6) | 0.1525 (5) | 0.0381 (14) | |
C21 | 1.1045 (8) | 1.0660 (7) | 0.1440 (6) | 0.0473 (16) | |
H21 | 1.1892 | 1.0198 | 0.1674 | 0.057* | |
C22 | 1.1176 (8) | 1.1862 (8) | 0.1015 (6) | 0.0523 (17) | |
H22 | 1.2109 | 1.2221 | 0.0958 | 0.063* | |
C23 | 0.9917 (7) | 1.2540 (7) | 0.0671 (6) | 0.0452 (15) | |
H23 | 1.0009 | 1.3363 | 0.0390 | 0.054* | |
C24 | 0.8465 (7) | 1.0885 (7) | 0.1143 (6) | 0.0419 (14) | |
H24 | 0.7518 | 1.0552 | 0.1182 | 0.050* | |
Cl1 | 0.4617 (2) | −0.1547 (2) | 1.0667 (2) | 0.0679 (6) | |
Cl2 | 0.2783 (2) | −0.52263 (19) | 1.0097 (2) | 0.0712 (6) | |
Hg1 | 0.36668 (3) | −0.32236 (2) | 0.99358 (2) | 0.04437 (13) | |
N1 | 0.5032 (7) | −0.3086 (6) | 0.7976 (5) | 0.0481 (14) | |
N2 | 0.8577 (6) | 1.2051 (5) | 0.0729 (5) | 0.0424 (12) | |
O1 | 0.7901 (7) | 0.2962 (5) | 0.4652 (4) | 0.0649 (15) | |
O2 | 0.8583 (10) | 0.5138 (7) | 0.3240 (6) | 0.099 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.080 (6) | 0.056 (5) | 0.063 (5) | −0.027 (4) | −0.006 (4) | 0.010 (4) |
C2 | 0.106 (7) | 0.051 (5) | 0.058 (5) | −0.017 (5) | 0.002 (5) | −0.013 (4) |
C3 | 0.076 (5) | 0.055 (5) | 0.042 (4) | −0.015 (4) | 0.002 (3) | −0.003 (3) |
C4 | 0.041 (3) | 0.051 (4) | 0.042 (3) | −0.005 (3) | −0.006 (3) | −0.004 (3) |
C5 | 0.050 (4) | 0.043 (4) | 0.046 (4) | −0.005 (3) | −0.008 (3) | −0.002 (3) |
C6 | 0.042 (3) | 0.052 (4) | 0.037 (3) | −0.007 (3) | −0.009 (3) | 0.005 (3) |
C7 | 0.066 (4) | 0.044 (4) | 0.045 (4) | 0.000 (3) | 0.008 (3) | −0.001 (3) |
C8 | 0.065 (4) | 0.051 (5) | 0.044 (4) | −0.012 (4) | 0.010 (3) | 0.004 (3) |
C9 | 0.068 (4) | 0.046 (4) | 0.037 (3) | −0.012 (3) | −0.011 (3) | 0.007 (3) |
C10 | 0.070 (5) | 0.039 (4) | 0.055 (4) | 0.002 (4) | 0.000 (4) | −0.005 (3) |
C11 | 0.055 (4) | 0.049 (5) | 0.048 (4) | −0.008 (3) | 0.001 (3) | 0.000 (3) |
C12 | 0.137 (9) | 0.044 (5) | 0.068 (6) | −0.021 (6) | 0.018 (6) | 0.006 (4) |
C13 | 0.082 (7) | 0.106 (10) | 0.099 (8) | −0.021 (7) | −0.017 (6) | 0.012 (7) |
C14 | 0.074 (5) | 0.039 (4) | 0.053 (4) | −0.004 (4) | 0.006 (4) | 0.004 (3) |
C15 | 0.066 (5) | 0.057 (5) | 0.069 (5) | 0.004 (4) | −0.015 (4) | 0.021 (4) |
C16 | 0.043 (4) | 0.053 (5) | 0.071 (5) | −0.002 (3) | −0.012 (3) | 0.013 (4) |
C17 | 0.041 (3) | 0.038 (4) | 0.036 (3) | 0.002 (3) | −0.003 (2) | −0.001 (3) |
C18 | 0.050 (4) | 0.045 (4) | 0.048 (4) | −0.011 (3) | −0.008 (3) | 0.004 (3) |
C19 | 0.056 (4) | 0.049 (5) | 0.061 (4) | −0.016 (4) | −0.004 (3) | 0.001 (4) |
C20 | 0.037 (3) | 0.042 (4) | 0.033 (3) | −0.003 (3) | −0.002 (2) | −0.003 (3) |
C21 | 0.037 (3) | 0.053 (5) | 0.052 (4) | −0.004 (3) | −0.009 (3) | 0.001 (3) |
C22 | 0.040 (3) | 0.054 (5) | 0.063 (4) | −0.011 (3) | −0.011 (3) | 0.006 (4) |
C23 | 0.047 (4) | 0.042 (4) | 0.048 (4) | −0.009 (3) | −0.010 (3) | 0.006 (3) |
C24 | 0.032 (3) | 0.044 (4) | 0.049 (3) | −0.008 (3) | −0.005 (3) | 0.002 (3) |
Cl1 | 0.0470 (9) | 0.0656 (14) | 0.0960 (15) | −0.0068 (9) | −0.0162 (9) | −0.0325 (12) |
Cl2 | 0.0617 (11) | 0.0361 (11) | 0.1196 (18) | −0.0200 (9) | −0.0248 (12) | 0.0203 (11) |
Hg1 | 0.04736 (18) | 0.03537 (19) | 0.05181 (19) | −0.01233 (12) | −0.01111 (12) | 0.00770 (12) |
N1 | 0.054 (3) | 0.044 (4) | 0.045 (3) | −0.015 (3) | −0.005 (3) | 0.007 (3) |
N2 | 0.040 (3) | 0.038 (3) | 0.048 (3) | −0.010 (2) | −0.006 (2) | 0.005 (2) |
O1 | 0.103 (4) | 0.042 (3) | 0.047 (3) | −0.019 (3) | −0.002 (3) | 0.001 (2) |
O2 | 0.117 (6) | 0.071 (5) | 0.083 (5) | 0.019 (4) | 0.016 (4) | 0.035 (4) |
C1—N1 | 1.322 (11) | C13—H13B | 0.9700 |
C1—C2 | 1.392 (12) | C14—C19 | 1.377 (12) |
C1—H1 | 0.9300 | C14—C15 | 1.388 (12) |
C2—C3 | 1.355 (12) | C14—O2 | 1.414 (11) |
C2—H2 | 0.9300 | C15—C16 | 1.395 (12) |
C3—C4 | 1.395 (11) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.378 (10) |
C4—C5 | 1.413 (10) | C16—H16 | 0.9300 |
C4—C6 | 1.469 (10) | C17—C18 | 1.418 (9) |
C5—N1 | 1.314 (9) | C17—C20 | 1.475 (10) |
C5—H5 | 0.9300 | C18—C19 | 1.364 (11) |
C6—C7 | 1.387 (9) | C18—H18 | 0.9300 |
C6—C11 | 1.392 (10) | C19—H19 | 0.9300 |
C7—C8 | 1.364 (11) | C20—C24 | 1.384 (9) |
C7—H7 | 0.9300 | C20—C21 | 1.396 (9) |
C8—C9 | 1.378 (11) | C21—C22 | 1.362 (11) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—O1 | 1.358 (9) | C22—C23 | 1.376 (10) |
C9—C10 | 1.381 (11) | C22—H22 | 0.9300 |
C10—C11 | 1.370 (11) | C23—N2 | 1.326 (8) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—N2 | 1.322 (9) |
C12—O1 | 1.433 (10) | C24—H24 | 0.9300 |
C12—C13 | 1.547 (15) | Cl1—Hg1 | 2.337 (2) |
C12—H12A | 0.9700 | Cl2—Hg1 | 2.338 (2) |
C12—H12B | 0.9700 | Hg1—N1 | 2.438 (6) |
C13—O2 | 1.306 (13) | Hg1—N2i | 2.463 (5) |
C13—H13A | 0.9700 | N2—Hg1i | 2.463 (5) |
N1—C1—C2 | 122.8 (8) | C19—C14—O2 | 114.0 (8) |
N1—C1—H1 | 118.6 | C15—C14—O2 | 126.6 (8) |
C2—C1—H1 | 118.6 | C14—C15—C16 | 119.2 (7) |
C3—C2—C1 | 118.6 (8) | C14—C15—H15 | 120.4 |
C3—C2—H2 | 120.7 | C16—C15—H15 | 120.4 |
C1—C2—H2 | 120.7 | C17—C16—C15 | 123.0 (8) |
C2—C3—C4 | 121.3 (7) | C17—C16—H16 | 118.5 |
C2—C3—H3 | 119.4 | C15—C16—H16 | 118.5 |
C4—C3—H3 | 119.4 | C16—C17—C18 | 115.6 (7) |
C3—C4—C5 | 114.2 (7) | C16—C17—C20 | 123.4 (6) |
C3—C4—C6 | 123.7 (6) | C18—C17—C20 | 121.0 (6) |
C5—C4—C6 | 122.1 (6) | C19—C18—C17 | 122.3 (7) |
N1—C5—C4 | 125.7 (7) | C19—C18—H18 | 118.8 |
N1—C5—H5 | 117.2 | C17—C18—H18 | 118.8 |
C4—C5—H5 | 117.2 | C18—C19—C14 | 120.5 (7) |
C7—C6—C11 | 116.3 (7) | C18—C19—H19 | 119.8 |
C7—C6—C4 | 121.5 (6) | C14—C19—H19 | 119.8 |
C11—C6—C4 | 122.2 (6) | C24—C20—C21 | 115.1 (6) |
C8—C7—C6 | 122.4 (7) | C24—C20—C17 | 122.5 (6) |
C8—C7—H7 | 118.8 | C21—C20—C17 | 122.4 (6) |
C6—C7—H7 | 118.8 | C22—C21—C20 | 120.3 (6) |
C7—C8—C9 | 120.7 (7) | C22—C21—H21 | 119.8 |
C7—C8—H8 | 119.7 | C20—C21—H21 | 119.8 |
C9—C8—H8 | 119.7 | C21—C22—C23 | 119.5 (7) |
O1—C9—C8 | 124.5 (7) | C21—C22—H22 | 120.3 |
O1—C9—C10 | 117.5 (7) | C23—C22—H22 | 120.3 |
C8—C9—C10 | 118.0 (7) | N2—C23—C22 | 121.7 (7) |
C11—C10—C9 | 121.1 (7) | N2—C23—H23 | 119.1 |
C11—C10—H10 | 119.5 | C22—C23—H23 | 119.1 |
C9—C10—H10 | 119.5 | N2—C24—C20 | 125.2 (6) |
C10—C11—C6 | 121.5 (7) | N2—C24—H24 | 117.4 |
C10—C11—H11 | 119.2 | C20—C24—H24 | 117.4 |
C6—C11—H11 | 119.2 | Cl1—Hg1—Cl2 | 152.25 (10) |
O1—C12—C13 | 110.2 (8) | Cl1—Hg1—N1 | 100.05 (16) |
O1—C12—H12A | 109.6 | Cl2—Hg1—N1 | 103.08 (16) |
C13—C12—H12A | 109.6 | Cl1—Hg1—N2i | 98.41 (14) |
O1—C12—H12B | 109.6 | Cl2—Hg1—N2i | 98.11 (14) |
C13—C12—H12B | 109.6 | N1—Hg1—N2i | 86.50 (19) |
H12A—C12—H12B | 108.1 | C5—N1—C1 | 117.4 (6) |
O2—C13—C12 | 106.3 (10) | C5—N1—Hg1 | 121.2 (5) |
O2—C13—H13A | 110.5 | C1—N1—Hg1 | 121.3 (5) |
C12—C13—H13A | 110.5 | C24—N2—C23 | 118.1 (6) |
O2—C13—H13B | 110.5 | C24—N2—Hg1i | 119.5 (4) |
C12—C13—H13B | 110.5 | C23—N2—Hg1i | 122.3 (5) |
H13A—C13—H13B | 108.7 | C9—O1—C12 | 116.2 (6) |
C19—C14—C15 | 119.5 (8) | C13—O2—C14 | 117.0 (10) |
N1—C1—C2—C3 | −4.1 (15) | C16—C17—C20—C24 | −170.3 (6) |
C1—C2—C3—C4 | 3.9 (15) | C18—C17—C20—C24 | 10.3 (9) |
C2—C3—C4—C5 | −0.9 (12) | C16—C17—C20—C21 | 9.4 (10) |
C2—C3—C4—C6 | 178.5 (8) | C18—C17—C20—C21 | −170.0 (6) |
C3—C4—C5—N1 | −2.2 (11) | C24—C20—C21—C22 | 0.5 (9) |
C6—C4—C5—N1 | 178.3 (7) | C17—C20—C21—C22 | −179.2 (6) |
C3—C4—C6—C7 | −24.7 (11) | C20—C21—C22—C23 | 0.0 (11) |
C5—C4—C6—C7 | 154.7 (7) | C21—C22—C23—N2 | −0.8 (11) |
C3—C4—C6—C11 | 154.7 (7) | C21—C20—C24—N2 | −0.5 (9) |
C5—C4—C6—C11 | −25.9 (10) | C17—C20—C24—N2 | 179.2 (6) |
C11—C6—C7—C8 | 1.7 (11) | C4—C5—N1—C1 | 2.2 (11) |
C4—C6—C7—C8 | −178.9 (7) | C4—C5—N1—Hg1 | −174.5 (5) |
C6—C7—C8—C9 | −0.1 (13) | C2—C1—N1—C5 | 1.1 (13) |
C7—C8—C9—O1 | 178.3 (8) | C2—C1—N1—Hg1 | 177.8 (7) |
C7—C8—C9—C10 | −1.8 (12) | Cl1—Hg1—N1—C5 | −26.4 (5) |
O1—C9—C10—C11 | −178.1 (7) | Cl2—Hg1—N1—C5 | 169.1 (5) |
C8—C9—C10—C11 | 2.0 (12) | N2i—Hg1—N1—C5 | 71.6 (5) |
C9—C10—C11—C6 | −0.3 (12) | Cl1—Hg1—N1—C1 | 157.1 (6) |
C7—C6—C11—C10 | −1.5 (11) | Cl2—Hg1—N1—C1 | −7.5 (6) |
C4—C6—C11—C10 | 179.1 (7) | N2i—Hg1—N1—C1 | −105.0 (6) |
O1—C12—C13—O2 | −71.5 (12) | C20—C24—N2—C23 | −0.2 (10) |
C19—C14—C15—C16 | 0.1 (12) | C20—C24—N2—Hg1i | 178.8 (5) |
O2—C14—C15—C16 | 179.1 (8) | C22—C23—N2—C24 | 0.9 (10) |
C14—C15—C16—C17 | 0.2 (13) | C22—C23—N2—Hg1i | −178.1 (5) |
C15—C16—C17—C18 | −0.4 (11) | C8—C9—O1—C12 | 3.2 (12) |
C15—C16—C17—C20 | −179.9 (7) | C10—C9—O1—C12 | −176.7 (8) |
C16—C17—C18—C19 | 0.5 (10) | C13—C12—O1—C9 | −165.7 (8) |
C20—C17—C18—C19 | 180.0 (6) | C12—C13—O2—C14 | −168.2 (8) |
C17—C18—C19—C14 | −0.3 (11) | C19—C14—O2—C13 | 165.6 (9) |
C15—C14—C19—C18 | 0.0 (11) | C15—C14—O2—C13 | −13.5 (14) |
O2—C14—C19—C18 | −179.1 (7) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
[Hg2Br4(C24H20N2O2)2] | Z = 1 |
Mr = 1457.66 | F(000) = 688 |
Triclinic, P1 | Dx = 2.106 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.021 (4) Å | Cell parameters from 2261 reflections |
b = 11.096 (4) Å | θ = 2.3–23.2° |
c = 11.914 (5) Å | µ = 10.20 mm−1 |
α = 81.812 (5)° | T = 298 K |
β = 78.764 (5)° | Block, colourless |
γ = 81.635 (5)° | 0.15 × 0.14 × 0.13 mm |
V = 1149.1 (8) Å3 |
Bruker SMART CCD area-detector diffractometer | 4234 independent reflections |
Radiation source: fine-focus sealed tube | 3491 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 25.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→9 |
Tmin = 0.310, Tmax = 0.351 | k = −13→7 |
6112 measured reflections | l = −14→14 |
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) = 0.100 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.1447P] where P = (Fo2 + 2Fc2)/3 |
4234 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 1.19 e Å−3 |
0 restraints | Δρmin = −1.04 e Å−3 |
[Hg2Br4(C24H20N2O2)2] | γ = 81.635 (5)° |
Mr = 1457.66 | V = 1149.1 (8) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.021 (4) Å | Mo Kα radiation |
b = 11.096 (4) Å | µ = 10.20 mm−1 |
c = 11.914 (5) Å | T = 298 K |
α = 81.812 (5)° | 0.15 × 0.14 × 0.13 mm |
β = 78.764 (5)° |
Bruker SMART CCD area-detector diffractometer | 4234 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3491 reflections with I > 2σ(I) |
Tmin = 0.310, Tmax = 0.351 | Rint = 0.025 |
6112 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | Δρmax = 1.19 e Å−3 |
4234 reflections | Δρmin = −1.04 e Å−3 |
280 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 | ||
Br1 | 0.46032 (8) | −0.16667 (8) | 1.06539 (8) | 0.0674 (2) | |
Br2 | 0.25820 (11) | −0.52762 (8) | 1.02646 (10) | 0.0853 (3) | |
C1 | 0.4994 (10) | −0.3976 (8) | 0.7275 (8) | 0.080 (3) | |
H1 | 0.4598 | −0.4703 | 0.7590 | 0.095* | |
C2 | 0.5734 (12) | −0.3894 (9) | 0.6154 (8) | 0.088 (3) | |
H2 | 0.5876 | −0.4555 | 0.5728 | 0.105* | |
C3 | 0.6271 (11) | −0.2775 (9) | 0.5671 (7) | 0.079 (3) | |
H3 | 0.6766 | −0.2681 | 0.4908 | 0.095* | |
C4 | 0.6066 (7) | −0.1812 (7) | 0.6325 (6) | 0.0527 (17) | |
C5 | 0.5342 (8) | −0.2045 (7) | 0.7467 (6) | 0.0540 (17) | |
H5 | 0.5224 | −0.1422 | 0.7935 | 0.065* | |
C6 | 0.6596 (8) | −0.0593 (7) | 0.5874 (6) | 0.0516 (17) | |
C7 | 0.7724 (9) | −0.0468 (7) | 0.4912 (6) | 0.063 (2) | |
H7 | 0.8144 | −0.1155 | 0.4543 | 0.076* | |
C8 | 0.8246 (9) | 0.0643 (8) | 0.4482 (6) | 0.068 (2) | |
H8 | 0.9004 | 0.0698 | 0.3831 | 0.082* | |
C9 | 0.7647 (8) | 0.1669 (7) | 0.5013 (6) | 0.0555 (18) | |
C10 | 0.6499 (9) | 0.1575 (8) | 0.5974 (6) | 0.063 (2) | |
H10 | 0.6076 | 0.2262 | 0.6343 | 0.075* | |
C11 | 0.5987 (8) | 0.0439 (7) | 0.6380 (6) | 0.0586 (19) | |
H11 | 0.5207 | 0.0383 | 0.7016 | 0.070* | |
C12 | 0.9231 (10) | 0.2928 (7) | 0.3664 (7) | 0.074 (2) | |
H12A | 0.8797 | 0.2843 | 0.3000 | 0.089* | |
H12B | 1.0077 | 0.2287 | 0.3718 | 0.089* | |
C13 | 0.9791 (10) | 0.4190 (8) | 0.3523 (8) | 0.084 (3) | |
H13A | 1.0066 | 0.4339 | 0.4235 | 0.101* | |
H13B | 1.0677 | 0.4235 | 0.2916 | 0.101* | |
C14 | 0.8920 (8) | 0.6250 (8) | 0.2874 (6) | 0.061 (2) | |
C15 | 1.0254 (9) | 0.6680 (8) | 0.2959 (7) | 0.068 (2) | |
H15 | 1.1008 | 0.6165 | 0.3283 | 0.082* | |
C16 | 1.0450 (8) | 0.7904 (8) | 0.2547 (7) | 0.065 (2) | |
H16 | 1.1337 | 0.8198 | 0.2621 | 0.078* | |
C17 | 0.9381 (7) | 0.8686 (6) | 0.2037 (5) | 0.0466 (16) | |
C18 | 0.8060 (8) | 0.8216 (7) | 0.1966 (7) | 0.0589 (19) | |
H18 | 0.7306 | 0.8722 | 0.1633 | 0.071* | |
C19 | 0.7842 (8) | 0.7028 (7) | 0.2373 (7) | 0.0609 (19) | |
H19 | 0.6946 | 0.6742 | 0.2309 | 0.073* | |
C20 | 0.9624 (7) | 0.9977 (6) | 0.1582 (5) | 0.0420 (15) | |
C21 | 1.0991 (8) | 1.0437 (7) | 0.1515 (7) | 0.0598 (19) | |
H21 | 1.1804 | 0.9932 | 0.1773 | 0.072* | |
C22 | 1.1160 (8) | 1.1646 (7) | 0.1064 (7) | 0.062 (2) | |
H22 | 1.2079 | 1.1953 | 0.1016 | 0.074* | |
C23 | 0.9955 (8) | 1.2374 (7) | 0.0694 (6) | 0.0563 (18) | |
H23 | 1.0065 | 1.3186 | 0.0403 | 0.068* | |
C24 | 0.8515 (8) | 1.0791 (7) | 0.1161 (6) | 0.0531 (17) | |
H24 | 0.7593 | 1.0504 | 0.1170 | 0.064* | |
Hg1 | 0.35219 (3) | −0.32686 (2) | 0.99462 (2) | 0.05355 (13) | |
N1 | 0.4807 (7) | −0.3094 (6) | 0.7936 (5) | 0.0601 (15) | |
N2 | 0.8637 (6) | 1.1967 (5) | 0.0734 (5) | 0.0515 (14) | |
O1 | 0.8105 (6) | 0.2816 (5) | 0.4685 (4) | 0.0705 (15) | |
O2 | 0.8578 (6) | 0.5059 (5) | 0.3240 (5) | 0.0792 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0517 (4) | 0.0724 (5) | 0.0860 (6) | −0.0108 (4) | −0.0146 (4) | −0.0296 (5) |
Br2 | 0.0754 (5) | 0.0491 (5) | 0.1318 (9) | −0.0217 (4) | −0.0170 (5) | 0.0004 (5) |
C1 | 0.095 (7) | 0.067 (5) | 0.084 (7) | −0.038 (5) | −0.011 (5) | −0.008 (5) |
C2 | 0.118 (8) | 0.082 (6) | 0.072 (6) | −0.040 (6) | −0.002 (5) | −0.028 (5) |
C3 | 0.094 (6) | 0.095 (7) | 0.051 (5) | −0.021 (6) | −0.002 (4) | −0.020 (5) |
C4 | 0.044 (4) | 0.061 (5) | 0.054 (4) | −0.005 (3) | −0.010 (3) | −0.011 (4) |
C5 | 0.056 (4) | 0.058 (4) | 0.048 (4) | −0.010 (4) | −0.004 (3) | −0.008 (4) |
C6 | 0.049 (4) | 0.062 (5) | 0.045 (4) | −0.008 (3) | −0.012 (3) | −0.004 (3) |
C7 | 0.074 (5) | 0.063 (5) | 0.043 (4) | 0.001 (4) | 0.008 (3) | −0.014 (4) |
C8 | 0.072 (5) | 0.084 (6) | 0.039 (4) | −0.011 (5) | 0.014 (3) | −0.003 (4) |
C9 | 0.059 (4) | 0.069 (5) | 0.036 (4) | −0.007 (4) | −0.005 (3) | −0.002 (4) |
C10 | 0.069 (5) | 0.068 (5) | 0.048 (4) | −0.008 (4) | −0.001 (4) | −0.011 (4) |
C11 | 0.054 (4) | 0.072 (5) | 0.047 (4) | −0.016 (4) | 0.005 (3) | −0.007 (4) |
C12 | 0.092 (6) | 0.061 (5) | 0.056 (5) | −0.004 (5) | 0.007 (4) | 0.003 (4) |
C13 | 0.077 (6) | 0.088 (7) | 0.074 (6) | −0.004 (5) | −0.005 (5) | 0.021 (5) |
C14 | 0.056 (4) | 0.076 (5) | 0.046 (4) | −0.005 (4) | 0.001 (3) | −0.003 (4) |
C15 | 0.058 (5) | 0.071 (5) | 0.068 (5) | −0.003 (4) | −0.016 (4) | 0.018 (4) |
C16 | 0.047 (4) | 0.083 (6) | 0.064 (5) | −0.009 (4) | −0.017 (3) | 0.005 (4) |
C17 | 0.037 (3) | 0.060 (4) | 0.041 (4) | 0.002 (3) | −0.002 (3) | −0.015 (3) |
C18 | 0.050 (4) | 0.055 (4) | 0.075 (5) | −0.002 (4) | −0.018 (4) | −0.013 (4) |
C19 | 0.057 (4) | 0.065 (5) | 0.065 (5) | −0.014 (4) | −0.019 (4) | −0.005 (4) |
C20 | 0.038 (3) | 0.056 (4) | 0.033 (3) | −0.006 (3) | −0.003 (3) | −0.014 (3) |
C21 | 0.037 (4) | 0.069 (5) | 0.073 (5) | 0.003 (3) | −0.009 (3) | −0.015 (4) |
C22 | 0.038 (4) | 0.069 (5) | 0.082 (6) | −0.005 (4) | −0.015 (4) | −0.015 (4) |
C23 | 0.046 (4) | 0.054 (4) | 0.068 (5) | −0.011 (3) | −0.001 (3) | −0.010 (4) |
C24 | 0.044 (4) | 0.061 (5) | 0.058 (4) | −0.013 (3) | −0.013 (3) | −0.007 (4) |
Hg1 | 0.05616 (19) | 0.04413 (18) | 0.0619 (2) | −0.01459 (13) | −0.01151 (13) | −0.00151 (13) |
N1 | 0.065 (4) | 0.060 (4) | 0.056 (4) | −0.017 (3) | −0.011 (3) | −0.003 (3) |
N2 | 0.045 (3) | 0.056 (4) | 0.054 (4) | −0.010 (3) | −0.006 (3) | −0.007 (3) |
O1 | 0.086 (4) | 0.069 (4) | 0.050 (3) | −0.017 (3) | 0.001 (3) | 0.004 (3) |
O2 | 0.073 (4) | 0.069 (4) | 0.085 (4) | −0.010 (3) | −0.009 (3) | 0.021 (3) |
C1—N1 | 1.314 (10) | C13—H13B | 0.9700 |
C1—C2 | 1.369 (13) | C14—C19 | 1.373 (10) |
C1—H1 | 0.9300 | C14—C15 | 1.384 (10) |
C2—C3 | 1.404 (12) | C14—O2 | 1.390 (9) |
C2—H2 | 0.9300 | C15—C16 | 1.401 (11) |
C3—C4 | 1.380 (11) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.374 (9) |
C4—C5 | 1.396 (10) | C16—H16 | 0.9300 |
C4—C6 | 1.492 (10) | C17—C18 | 1.390 (9) |
C5—N1 | 1.331 (9) | C17—C20 | 1.489 (9) |
C5—H5 | 0.9300 | C18—C19 | 1.366 (10) |
C6—C11 | 1.364 (10) | C18—H18 | 0.9300 |
C6—C7 | 1.382 (10) | C19—H19 | 0.9300 |
C7—C8 | 1.378 (11) | C20—C24 | 1.369 (9) |
C7—H7 | 0.9300 | C20—C21 | 1.385 (9) |
C8—C9 | 1.371 (10) | C21—C22 | 1.391 (10) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—O1 | 1.376 (9) | C22—C23 | 1.363 (10) |
C9—C10 | 1.389 (10) | C22—H22 | 0.9300 |
C10—C11 | 1.394 (10) | C23—N2 | 1.322 (8) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—N2 | 1.343 (9) |
C12—O1 | 1.428 (9) | C24—H24 | 0.9300 |
C12—C13 | 1.533 (12) | Br1—Hg1 | 2.4644 (10) |
C12—H12A | 0.9700 | Br2—Hg1 | 2.4512 (12) |
C12—H12B | 0.9700 | Hg1—N1 | 2.443 (6) |
C13—O2 | 1.410 (9) | Hg1—N2i | 2.449 (5) |
C13—H13A | 0.9700 | N2—Hg1i | 2.449 (5) |
N1—C1—C2 | 124.3 (8) | C19—C14—O2 | 115.9 (7) |
N1—C1—H1 | 117.9 | C15—C14—O2 | 125.0 (7) |
C2—C1—H1 | 117.9 | C14—C15—C16 | 118.9 (7) |
C1—C2—C3 | 117.5 (8) | C14—C15—H15 | 120.6 |
C1—C2—H2 | 121.3 | C16—C15—H15 | 120.6 |
C3—C2—H2 | 121.3 | C17—C16—C15 | 122.4 (7) |
C4—C3—C2 | 120.2 (8) | C17—C16—H16 | 118.8 |
C4—C3—H3 | 119.9 | C15—C16—H16 | 118.8 |
C2—C3—H3 | 119.9 | C16—C17—C18 | 116.9 (7) |
C3—C4—C5 | 115.8 (7) | C16—C17—C20 | 121.6 (6) |
C3—C4—C6 | 123.5 (7) | C18—C17—C20 | 121.5 (6) |
C5—C4—C6 | 120.7 (6) | C19—C18—C17 | 121.6 (7) |
N1—C5—C4 | 124.8 (7) | C19—C18—H18 | 119.2 |
N1—C5—H5 | 117.6 | C17—C18—H18 | 119.2 |
C4—C5—H5 | 117.6 | C18—C19—C14 | 121.2 (7) |
C11—C6—C7 | 117.3 (7) | C18—C19—H19 | 119.4 |
C11—C6—C4 | 121.9 (6) | C14—C19—H19 | 119.4 |
C7—C6—C4 | 120.8 (7) | C24—C20—C21 | 114.9 (6) |
C8—C7—C6 | 122.1 (7) | C24—C20—C17 | 121.9 (6) |
C8—C7—H7 | 119.0 | C21—C20—C17 | 123.2 (6) |
C6—C7—H7 | 119.0 | C20—C21—C22 | 120.6 (7) |
C9—C8—C7 | 120.0 (7) | C20—C21—H21 | 119.7 |
C9—C8—H8 | 120.0 | C22—C21—H21 | 119.7 |
C7—C8—H8 | 120.0 | C23—C22—C21 | 118.9 (7) |
C8—C9—O1 | 125.3 (6) | C23—C22—H22 | 120.5 |
C8—C9—C10 | 119.2 (7) | C21—C22—H22 | 120.5 |
O1—C9—C10 | 115.5 (7) | N2—C23—C22 | 122.3 (7) |
C9—C10—C11 | 119.3 (7) | N2—C23—H23 | 118.8 |
C9—C10—H10 | 120.4 | C22—C23—H23 | 118.8 |
C11—C10—H10 | 120.4 | N2—C24—C20 | 125.9 (6) |
C6—C11—C10 | 122.1 (7) | N2—C24—H24 | 117.1 |
C6—C11—H11 | 119.0 | C20—C24—H24 | 117.1 |
C10—C11—H11 | 119.0 | Br1—Hg1—Br2 | 150.17 (4) |
O1—C12—C13 | 108.9 (7) | Br1—Hg1—N1 | 100.18 (15) |
O1—C12—H12A | 109.9 | Br2—Hg1—N1 | 104.22 (15) |
C13—C12—H12A | 109.9 | N2i—Hg1—Br1 | 97.82 (14) |
O1—C12—H12B | 109.9 | N2i—Hg1—Br2 | 100.51 (14) |
C13—C12—H12B | 109.9 | N1—Hg1—N2i | 86.53 (19) |
H12A—C12—H12B | 108.3 | C1—N1—C5 | 117.3 (7) |
O2—C13—C12 | 106.5 (7) | C1—N1—Hg1 | 123.8 (5) |
O2—C13—H13A | 110.4 | C5—N1—Hg1 | 118.9 (5) |
C12—C13—H13A | 110.4 | C23—N2—C24 | 117.4 (6) |
O2—C13—H13B | 110.4 | C23—N2—Hg1i | 122.4 (5) |
C12—C13—H13B | 110.4 | C24—N2—Hg1i | 120.2 (4) |
H13A—C13—H13B | 108.6 | C9—O1—C12 | 115.5 (6) |
C19—C14—C15 | 119.0 (7) | C14—O2—C13 | 116.2 (6) |
N1—C1—C2—C3 | −2.7 (16) | C16—C17—C20—C24 | −174.5 (7) |
C1—C2—C3—C4 | 0.9 (14) | C18—C17—C20—C24 | 5.5 (10) |
C2—C3—C4—C5 | 1.4 (12) | C16—C17—C20—C21 | 7.9 (10) |
C2—C3—C4—C6 | −179.7 (8) | C18—C17—C20—C21 | −172.2 (7) |
C3—C4—C5—N1 | −2.4 (11) | C24—C20—C21—C22 | 1.1 (10) |
C6—C4—C5—N1 | 178.7 (6) | C17—C20—C21—C22 | 178.9 (7) |
C3—C4—C6—C11 | 158.8 (8) | C20—C21—C22—C23 | 0.2 (12) |
C5—C4—C6—C11 | −22.3 (10) | C21—C22—C23—N2 | −0.9 (12) |
C3—C4—C6—C7 | −20.7 (11) | C21—C20—C24—N2 | −2.0 (10) |
C5—C4—C6—C7 | 158.2 (7) | C17—C20—C24—N2 | −179.9 (6) |
C11—C6—C7—C8 | 1.1 (12) | C2—C1—N1—C5 | 1.8 (14) |
C4—C6—C7—C8 | −179.4 (7) | C2—C1—N1—Hg1 | −178.9 (8) |
C6—C7—C8—C9 | 0.2 (13) | C4—C5—N1—C1 | 0.8 (11) |
C7—C8—C9—O1 | 178.0 (7) | C4—C5—N1—Hg1 | −178.5 (5) |
C7—C8—C9—C10 | −0.9 (12) | N2i—Hg1—N1—C1 | −104.7 (7) |
C8—C9—C10—C11 | 0.3 (11) | Br2—Hg1—N1—C1 | −4.7 (7) |
O1—C9—C10—C11 | −178.7 (7) | Br1—Hg1—N1—C1 | 158.0 (6) |
C7—C6—C11—C10 | −1.7 (11) | N2i—Hg1—N1—C5 | 74.6 (5) |
C4—C6—C11—C10 | 178.8 (7) | Br2—Hg1—N1—C5 | 174.5 (5) |
C9—C10—C11—C6 | 1.1 (12) | Br1—Hg1—N1—C5 | −22.8 (5) |
O1—C12—C13—O2 | −70.1 (9) | C22—C23—N2—C24 | 0.1 (10) |
C19—C14—C15—C16 | 1.1 (12) | C22—C23—N2—Hg1i | −179.4 (6) |
O2—C14—C15—C16 | 179.6 (7) | C20—C24—N2—C23 | 1.5 (10) |
C14—C15—C16—C17 | −1.6 (12) | C20—C24—N2—Hg1i | −179.0 (5) |
C15—C16—C17—C18 | 1.3 (11) | C8—C9—O1—C12 | 4.1 (11) |
C15—C16—C17—C20 | −178.7 (7) | C10—C9—O1—C12 | −177.0 (7) |
C16—C17—C18—C19 | −0.7 (11) | C13—C12—O1—C9 | −171.3 (6) |
C20—C17—C18—C19 | 179.4 (7) | C19—C14—O2—C13 | 166.8 (7) |
C17—C18—C19—C14 | 0.3 (12) | C15—C14—O2—C13 | −11.8 (11) |
C15—C14—C19—C18 | −0.5 (12) | C12—C13—O2—C14 | −169.1 (7) |
O2—C14—C19—C18 | −179.1 (7) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
[Hg2I4(C24H20N2O2)2] | Z = 1 |
Mr = 1645.62 | F(000) = 760 |
Triclinic, P1 | Dx = 2.252 Mg m−3 |
Hall symbol: -p 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9444 (16) Å | Cell parameters from 3275 reflections |
b = 12.352 (2) Å | θ = 2.4–27.0° |
c = 12.052 (2) Å | µ = 8.91 mm−1 |
α = 72.641 (2)° | T = 298 K |
β = 74.882 (2)° | Block, colourless |
γ = 77.620 (2)° | 0.20 × 0.15 × 0.15 mm |
V = 1213.3 (4) Å3 |
Bruker SMART CCD area-detector diffractometer | 4426 independent reflections |
Radiation source: fine-focus sealed tube | 3740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→10 |
Tmin = 0.269, Tmax = 0.348 | k = −14→14 |
6387 measured reflections | l = −12→14 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3 |
4426 reflections | (Δ/σ)max = 0.001 |
280 parameters | Δρmax = 1.11 e Å−3 |
1 restraint | Δρmin = −1.10 e Å−3 |
[Hg2I4(C24H20N2O2)2] | γ = 77.620 (2)° |
Mr = 1645.62 | V = 1213.3 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.9444 (16) Å | Mo Kα radiation |
b = 12.352 (2) Å | µ = 8.91 mm−1 |
c = 12.052 (2) Å | T = 298 K |
α = 72.641 (2)° | 0.20 × 0.15 × 0.15 mm |
β = 74.882 (2)° |
Bruker SMART CCD area-detector diffractometer | 4426 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3740 reflections with I > 2σ(I) |
Tmin = 0.269, Tmax = 0.348 | Rint = 0.023 |
6387 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 1 restraint |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.11 e Å−3 |
4426 reflections | Δρmin = −1.10 e Å−3 |
280 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 | ||
C1 | 0.5421 (7) | −0.3617 (6) | 0.7284 (6) | 0.0512 (15) | |
H1 | 0.5164 | −0.4354 | 0.7611 | 0.061* | |
C2 | 0.6406 (9) | −0.3372 (6) | 0.6195 (7) | 0.065 (2) | |
H2 | 0.6806 | −0.3936 | 0.5784 | 0.079* | |
C3 | 0.6801 (8) | −0.2287 (6) | 0.5709 (7) | 0.065 (2) | |
H3 | 0.7487 | −0.2123 | 0.4974 | 0.078* | |
C4 | 0.6187 (6) | −0.1437 (5) | 0.6303 (5) | 0.0406 (13) | |
C5 | 0.5236 (7) | −0.1789 (5) | 0.7401 (5) | 0.0481 (15) | |
H5 | 0.4844 | −0.1253 | 0.7846 | 0.058* | |
C6 | 0.6549 (6) | −0.0249 (5) | 0.5844 (5) | 0.0405 (13) | |
C7 | 0.7775 (7) | 0.0037 (6) | 0.4901 (6) | 0.0534 (16) | |
H7 | 0.8399 | −0.0537 | 0.4562 | 0.064* | |
C8 | 0.8113 (8) | 0.1142 (6) | 0.4440 (6) | 0.0560 (17) | |
H8 | 0.8942 | 0.1306 | 0.3795 | 0.067* | |
C9 | 0.7217 (7) | 0.1999 (5) | 0.4939 (5) | 0.0432 (14) | |
C10 | 0.6013 (7) | 0.1732 (6) | 0.5879 (6) | 0.0523 (16) | |
H10 | 0.5412 | 0.2305 | 0.6228 | 0.063* | |
C11 | 0.5664 (7) | 0.0638 (5) | 0.6322 (6) | 0.0532 (16) | |
H11 | 0.4818 | 0.0486 | 0.6956 | 0.064* | |
C12 | 0.8457 (8) | 0.3461 (6) | 0.3417 (6) | 0.0526 (16) | |
H12A | 0.8244 | 0.3121 | 0.2856 | 0.063* | |
H12B | 0.9538 | 0.3193 | 0.3487 | 0.063* | |
C13 | 0.8204 (8) | 0.4731 (6) | 0.2980 (6) | 0.0553 (16) | |
H13A | 0.8616 | 0.4955 | 0.2129 | 0.066* | |
H13B | 0.7092 | 0.5018 | 0.3130 | 0.066* | |
C14 | 0.9126 (7) | 0.6343 (5) | 0.3114 (5) | 0.0425 (14) | |
C15 | 1.0155 (7) | 0.6758 (5) | 0.3514 (6) | 0.0491 (15) | |
H15 | 1.0703 | 0.6270 | 0.4076 | 0.059* | |
C16 | 1.0365 (7) | 0.7884 (5) | 0.3084 (5) | 0.0447 (14) | |
H16 | 1.1066 | 0.8143 | 0.3360 | 0.054* | |
C17 | 0.9571 (6) | 0.8658 (5) | 0.2248 (5) | 0.0365 (12) | |
C18 | 0.8547 (7) | 0.8219 (5) | 0.1869 (5) | 0.0440 (14) | |
H18 | 0.7997 | 0.8707 | 0.1309 | 0.053* | |
C19 | 0.8311 (7) | 0.7097 (6) | 0.2285 (6) | 0.0508 (16) | |
H19 | 0.7605 | 0.6839 | 0.2012 | 0.061* | |
C20 | 0.9810 (6) | 0.9871 (5) | 0.1800 (5) | 0.0373 (13) | |
C21 | 1.1090 (6) | 1.0272 (5) | 0.1905 (6) | 0.0454 (14) | |
H21 | 1.1860 | 0.9765 | 0.2268 | 0.054* | |
C22 | 1.1218 (7) | 1.1427 (6) | 0.1467 (6) | 0.0504 (16) | |
H22 | 1.2082 | 1.1694 | 0.1529 | 0.061* | |
C23 | 1.0089 (7) | 1.2176 (5) | 0.0946 (6) | 0.0460 (14) | |
H23 | 1.0189 | 1.2950 | 0.0657 | 0.055* | |
C24 | 0.8729 (7) | 1.0703 (5) | 0.1249 (5) | 0.0451 (14) | |
H24 | 0.7862 | 1.0462 | 0.1156 | 0.054* | |
Hg1 | 0.33105 (3) | −0.31840 (2) | 0.99668 (2) | 0.04913 (10) | |
I1 | 0.45290 (5) | −0.18407 (5) | 1.07191 (5) | 0.06595 (16) | |
I2 | 0.23304 (5) | −0.51441 (4) | 1.03272 (5) | 0.06082 (15) | |
N1 | 0.4828 (6) | −0.2833 (4) | 0.7883 (5) | 0.0491 (12) | |
N2 | 0.8836 (5) | 1.1814 (4) | 0.0843 (4) | 0.0425 (11) | |
O1 | 0.7450 (5) | 0.3123 (4) | 0.4541 (4) | 0.0538 (11) | |
O2 | 0.8984 (5) | 0.5213 (4) | 0.3581 (4) | 0.0547 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.055 (4) | 0.045 (4) | 0.056 (4) | −0.014 (3) | −0.020 (3) | −0.006 (3) |
C2 | 0.083 (5) | 0.047 (4) | 0.066 (5) | −0.008 (4) | −0.009 (4) | −0.020 (4) |
C3 | 0.073 (5) | 0.061 (5) | 0.055 (4) | −0.014 (4) | 0.007 (4) | −0.022 (4) |
C4 | 0.038 (3) | 0.040 (3) | 0.046 (3) | −0.001 (2) | −0.018 (3) | −0.009 (3) |
C5 | 0.047 (3) | 0.046 (4) | 0.045 (3) | −0.008 (3) | 0.001 (3) | −0.010 (3) |
C6 | 0.038 (3) | 0.048 (4) | 0.038 (3) | −0.005 (3) | −0.014 (3) | −0.009 (3) |
C7 | 0.055 (4) | 0.044 (4) | 0.056 (4) | −0.004 (3) | 0.002 (3) | −0.019 (3) |
C8 | 0.050 (4) | 0.053 (4) | 0.055 (4) | −0.018 (3) | 0.011 (3) | −0.011 (3) |
C9 | 0.044 (3) | 0.052 (4) | 0.040 (3) | −0.010 (3) | −0.015 (3) | −0.013 (3) |
C10 | 0.057 (4) | 0.052 (4) | 0.048 (4) | −0.005 (3) | −0.005 (3) | −0.021 (3) |
C11 | 0.049 (4) | 0.055 (4) | 0.047 (4) | −0.008 (3) | 0.005 (3) | −0.013 (3) |
C12 | 0.063 (4) | 0.056 (4) | 0.043 (3) | −0.019 (3) | −0.004 (3) | −0.017 (3) |
C13 | 0.067 (4) | 0.057 (4) | 0.048 (4) | −0.019 (3) | −0.020 (3) | −0.010 (3) |
C14 | 0.044 (3) | 0.044 (4) | 0.044 (3) | −0.007 (3) | −0.012 (3) | −0.016 (3) |
C15 | 0.053 (4) | 0.048 (4) | 0.052 (4) | −0.001 (3) | −0.026 (3) | −0.013 (3) |
C16 | 0.039 (3) | 0.049 (4) | 0.051 (4) | −0.005 (3) | −0.020 (3) | −0.011 (3) |
C17 | 0.031 (3) | 0.040 (3) | 0.037 (3) | −0.001 (2) | −0.004 (2) | −0.012 (2) |
C18 | 0.047 (3) | 0.039 (3) | 0.049 (3) | −0.004 (3) | −0.022 (3) | −0.008 (3) |
C19 | 0.052 (4) | 0.052 (4) | 0.060 (4) | −0.010 (3) | −0.030 (3) | −0.014 (3) |
C20 | 0.030 (3) | 0.047 (3) | 0.035 (3) | 0.000 (2) | −0.005 (2) | −0.016 (3) |
C21 | 0.035 (3) | 0.048 (4) | 0.060 (4) | −0.003 (3) | −0.019 (3) | −0.018 (3) |
C22 | 0.038 (3) | 0.055 (4) | 0.065 (4) | −0.009 (3) | −0.012 (3) | −0.022 (3) |
C23 | 0.045 (3) | 0.043 (4) | 0.052 (4) | −0.010 (3) | −0.013 (3) | −0.011 (3) |
C24 | 0.038 (3) | 0.049 (4) | 0.049 (3) | −0.009 (3) | −0.014 (3) | −0.007 (3) |
Hg1 | 0.05209 (16) | 0.04490 (16) | 0.05199 (16) | −0.01471 (11) | −0.01592 (12) | −0.00525 (11) |
I1 | 0.0506 (3) | 0.0845 (4) | 0.0802 (4) | −0.0097 (2) | −0.0164 (2) | −0.0450 (3) |
I2 | 0.0608 (3) | 0.0435 (3) | 0.0802 (3) | −0.0167 (2) | −0.0315 (2) | 0.0018 (2) |
N1 | 0.048 (3) | 0.045 (3) | 0.053 (3) | −0.008 (2) | −0.011 (2) | −0.010 (3) |
N2 | 0.036 (2) | 0.039 (3) | 0.051 (3) | −0.007 (2) | −0.010 (2) | −0.006 (2) |
O1 | 0.066 (3) | 0.046 (3) | 0.052 (3) | −0.014 (2) | −0.005 (2) | −0.019 (2) |
O2 | 0.073 (3) | 0.049 (3) | 0.051 (3) | −0.018 (2) | −0.026 (2) | −0.009 (2) |
C1—N1 | 1.318 (7) | C13—H13B | 0.9700 |
C1—C2 | 1.366 (10) | C14—O2 | 1.362 (7) |
C1—H1 | 0.9300 | C14—C15 | 1.387 (8) |
C2—C3 | 1.375 (10) | C14—C19 | 1.390 (9) |
C2—H2 | 0.9300 | C15—C16 | 1.367 (9) |
C3—C4 | 1.384 (8) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | C16—C17 | 1.393 (8) |
C4—C5 | 1.375 (8) | C16—H16 | 0.9300 |
C4—C6 | 1.479 (8) | C17—C18 | 1.387 (8) |
C5—N1 | 1.333 (8) | C17—C20 | 1.475 (8) |
C5—H5 | 0.9300 | C18—C19 | 1.367 (9) |
C6—C7 | 1.378 (9) | C18—H18 | 0.9300 |
C6—C11 | 1.388 (6) | C19—H19 | 0.9300 |
C7—C8 | 1.378 (9) | C20—C21 | 1.388 (7) |
C7—H7 | 0.9300 | C20—C24 | 1.391 (8) |
C8—C9 | 1.375 (8) | C21—C22 | 1.385 (9) |
C8—H8 | 0.9300 | C21—H21 | 0.9300 |
C9—C10 | 1.358 (8) | C22—C23 | 1.362 (9) |
C9—O1 | 1.369 (7) | C22—H22 | 0.9300 |
C10—C11 | 1.368 (9) | C23—N2 | 1.338 (7) |
C10—H10 | 0.9300 | C23—H23 | 0.9300 |
C11—H11 | 0.9300 | C24—N2 | 1.328 (7) |
C12—O1 | 1.416 (7) | C24—H24 | 0.9300 |
C12—C13 | 1.485 (9) | I1—Hg1 | 2.6365 (6) |
C12—H12A | 0.9700 | I2—Hg1 | 2.6272 (6) |
C12—H12B | 0.9700 | Hg1—N1 | 2.482 (5) |
C13—O2 | 1.437 (7) | Hg1—N2i | 2.471 (5) |
C13—H13A | 0.9700 | N2—Hg1i | 2.471 (5) |
N1—C1—C2 | 121.5 (6) | O2—C14—C19 | 124.8 (5) |
N1—C1—H1 | 119.2 | C15—C14—C19 | 118.6 (6) |
C2—C1—H1 | 119.2 | C16—C15—C14 | 120.1 (6) |
C1—C2—C3 | 119.6 (6) | C16—C15—H15 | 120.0 |
C1—C2—H2 | 120.2 | C14—C15—H15 | 120.0 |
C3—C2—H2 | 120.2 | C15—C16—C17 | 122.6 (5) |
C2—C3—C4 | 120.6 (7) | C15—C16—H16 | 118.7 |
C2—C3—H3 | 119.7 | C17—C16—H16 | 118.7 |
C4—C3—H3 | 119.7 | C18—C17—C16 | 115.9 (5) |
C5—C4—C3 | 114.5 (6) | C18—C17—C20 | 122.3 (5) |
C5—C4—C6 | 121.4 (5) | C16—C17—C20 | 121.7 (5) |
C3—C4—C6 | 124.1 (6) | C19—C18—C17 | 122.8 (6) |
N1—C5—C4 | 125.7 (6) | C19—C18—H18 | 118.6 |
N1—C5—H5 | 117.1 | C17—C18—H18 | 118.6 |
C4—C5—H5 | 117.1 | C18—C19—C14 | 120.0 (5) |
C7—C6—C11 | 116.4 (6) | C18—C19—H19 | 120.0 |
C7—C6—C4 | 121.4 (5) | C14—C19—H19 | 120.0 |
C11—C6—C4 | 122.2 (5) | C21—C20—C24 | 115.2 (6) |
C6—C7—C8 | 122.5 (5) | C21—C20—C17 | 123.5 (5) |
C6—C7—H7 | 118.8 | C24—C20—C17 | 121.3 (5) |
C8—C7—H7 | 118.8 | C22—C21—C20 | 119.8 (6) |
C9—C8—C7 | 119.6 (6) | C22—C21—H21 | 120.1 |
C9—C8—H8 | 120.2 | C20—C21—H21 | 120.1 |
C7—C8—H8 | 120.2 | C23—C22—C21 | 120.5 (6) |
C10—C9—O1 | 117.2 (5) | C23—C22—H22 | 119.8 |
C10—C9—C8 | 118.8 (6) | C21—C22—H22 | 119.8 |
O1—C9—C8 | 124.0 (6) | N2—C23—C22 | 120.9 (6) |
C9—C10—C11 | 121.5 (6) | N2—C23—H23 | 119.6 |
C9—C10—H10 | 119.3 | C22—C23—H23 | 119.6 |
C11—C10—H10 | 119.3 | N2—C24—C20 | 125.1 (5) |
C10—C11—C6 | 121.2 (6) | N2—C24—H24 | 117.4 |
C10—C11—H11 | 119.4 | C20—C24—H24 | 117.4 |
C6—C11—H11 | 119.4 | I1—Hg1—I2 | 149.69 (2) |
O1—C12—C13 | 109.6 (5) | I1—Hg1—N1 | 98.91 (12) |
O1—C12—H12A | 109.8 | I2—Hg1—N1 | 103.46 (12) |
C13—C12—H12A | 109.8 | N2i—Hg1—I1 | 100.74 (11) |
O1—C12—H12B | 109.8 | N2i—Hg1—I2 | 100.93 (11) |
C13—C12—H12B | 109.8 | N2i—Hg1—N1 | 86.14 (16) |
H12A—C12—H12B | 108.2 | C1—N1—C5 | 117.9 (6) |
O2—C13—C12 | 109.3 (5) | C1—N1—Hg1 | 125.7 (4) |
O2—C13—H13A | 109.8 | C5—N1—Hg1 | 115.7 (4) |
C12—C13—H13A | 109.8 | C24—N2—C23 | 118.5 (5) |
O2—C13—H13B | 109.8 | C24—N2—Hg1i | 120.4 (4) |
C12—C13—H13B | 109.8 | C23—N2—Hg1i | 121.1 (4) |
H13A—C13—H13B | 108.3 | C9—O1—C12 | 117.6 (4) |
O2—C14—C15 | 116.6 (5) | C14—O2—C13 | 116.1 (5) |
N1—C1—C2—C3 | 0.5 (11) | C18—C17—C20—C21 | −162.3 (5) |
C1—C2—C3—C4 | −1.3 (12) | C16—C17—C20—C21 | 17.8 (8) |
C2—C3—C4—C5 | 2.5 (10) | C18—C17—C20—C24 | 18.6 (8) |
C2—C3—C4—C6 | −179.9 (7) | C16—C17—C20—C24 | −161.3 (6) |
C3—C4—C5—N1 | −3.2 (9) | C24—C20—C21—C22 | −0.3 (8) |
C6—C4—C5—N1 | 179.1 (6) | C17—C20—C21—C22 | −179.5 (5) |
C5—C4—C6—C7 | 163.9 (6) | C20—C21—C22—C23 | 0.7 (9) |
C3—C4—C6—C7 | −13.6 (9) | C21—C22—C23—N2 | −0.1 (9) |
C5—C4—C6—C11 | −17.2 (9) | C21—C20—C24—N2 | −0.7 (9) |
C3—C4—C6—C11 | 165.4 (7) | C17—C20—C24—N2 | 178.5 (5) |
C11—C6—C7—C8 | −0.5 (10) | C2—C1—N1—C5 | −1.1 (9) |
C4—C6—C7—C8 | 178.5 (6) | C2—C1—N1—Hg1 | −171.6 (5) |
C6—C7—C8—C9 | 0.9 (11) | C4—C5—N1—C1 | 2.6 (9) |
C7—C8—C9—C10 | −0.1 (10) | C4—C5—N1—Hg1 | 174.1 (5) |
C7—C8—C9—O1 | −179.5 (6) | N2i—Hg1—N1—C1 | −120.7 (5) |
O1—C9—C10—C11 | 178.4 (6) | I2—Hg1—N1—C1 | −20.4 (5) |
C8—C9—C10—C11 | −1.0 (10) | I1—Hg1—N1—C1 | 139.0 (5) |
C9—C10—C11—C6 | 1.4 (10) | N2i—Hg1—N1—C5 | 68.6 (4) |
C7—C6—C11—C10 | −0.6 (10) | I2—Hg1—N1—C5 | 168.9 (4) |
C4—C6—C11—C10 | −179.6 (6) | I1—Hg1—N1—C5 | −31.7 (4) |
O1—C12—C13—O2 | 77.9 (7) | C20—C24—N2—C23 | 1.3 (9) |
O2—C14—C15—C16 | 179.8 (5) | C20—C24—N2—Hg1i | −175.1 (4) |
C19—C14—C15—C16 | −0.8 (9) | C22—C23—N2—C24 | −0.8 (9) |
C14—C15—C16—C17 | 0.4 (10) | C22—C23—N2—Hg1i | 175.5 (4) |
C15—C16—C17—C18 | −0.2 (9) | C10—C9—O1—C12 | −166.3 (6) |
C15—C16—C17—C20 | 179.7 (5) | C8—C9—O1—C12 | 13.1 (9) |
C16—C17—C18—C19 | 0.3 (9) | C13—C12—O1—C9 | 163.3 (5) |
C20—C17—C18—C19 | −179.6 (5) | C15—C14—O2—C13 | −166.5 (5) |
C17—C18—C19—C14 | −0.6 (10) | C19—C14—O2—C13 | 14.1 (9) |
O2—C14—C19—C18 | −179.8 (6) | C12—C13—O2—C14 | 167.4 (5) |
C15—C14—C19—C18 | 0.8 (9) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | [Hg2Cl4(C24H20N2O2)2] | [Hg2Br4(C24H20N2O2)2] | [Hg2I4(C24H20N2O2)2] |
Mr | 1279.82 | 1457.66 | 1645.62 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 298 | 298 | 298 |
a, b, c (Å) | 8.7822 (15), 10.6904 (18), 12.044 (2) | 9.021 (4), 11.096 (4), 11.914 (5) | 8.9444 (16), 12.352 (2), 12.052 (2) |
α, β, γ (°) | 86.662 (2), 78.930 (2), 84.014 (2) | 81.812 (5), 78.764 (5), 81.635 (5) | 72.641 (2), 74.882 (2), 77.620 (2) |
V (Å3) | 1102.8 (3) | 1149.1 (8) | 1213.3 (4) |
Z | 1 | 1 | 1 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 7.25 | 10.20 | 8.91 |
Crystal size (mm) | 0.20 × 0.15 × 0.15 | 0.15 × 0.14 × 0.13 | 0.20 × 0.15 × 0.15 |
Data collection | |||
Diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) | Multi-scan (SADABS; Bruker, 2003) | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.325, 0.410 | 0.310, 0.351 | 0.269, 0.348 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5867, 4066, 3708 | 6112, 4234, 3491 | 6387, 4426, 3740 |
Rint | 0.021 | 0.025 | 0.023 |
(sin θ/λ)max (Å−1) | 0.608 | 0.608 | 0.606 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.116, 1.08 | 0.040, 0.100, 1.08 | 0.034, 0.086, 1.02 |
No. of reflections | 4066 | 4234 | 4426 |
No. of parameters | 280 | 280 | 280 |
No. of restraints | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.99, −1.68 | 1.19, −1.04 | 1.11, −1.10 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cl1—Hg1 | 2.337 (2) | Hg1—N2i | 2.463 (5) |
Cl2—Hg1 | 2.338 (2) | N2—Hg1i | 2.463 (5) |
Hg1—N1 | 2.438 (6) | ||
Cl1—Hg1—Cl2 | 152.25 (10) | Cl1—Hg1—N2i | 98.41 (14) |
Cl1—Hg1—N1 | 100.05 (16) | Cl2—Hg1—N2i | 98.11 (14) |
Cl2—Hg1—N1 | 103.08 (16) | N1—Hg1—N2i | 86.50 (19) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Br1—Hg1 | 2.4644 (10) | Hg1—N2i | 2.449 (5) |
Br2—Hg1 | 2.4512 (12) | N2—Hg1i | 2.449 (5) |
Hg1—N1 | 2.443 (6) | ||
Br1—Hg1—Br2 | 150.17 (4) | N2i—Hg1—Br1 | 97.82 (14) |
Br1—Hg1—N1 | 100.18 (15) | N2i—Hg1—Br2 | 100.51 (14) |
Br2—Hg1—N1 | 104.22 (15) | N1—Hg1—N2i | 86.53 (19) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
I1—Hg1 | 2.6365 (6) | Hg1—N2i | 2.471 (5) |
I2—Hg1 | 2.6272 (6) | N2—Hg1i | 2.471 (5) |
Hg1—N1 | 2.482 (5) | ||
I1—Hg1—I2 | 149.69 (2) | N2i—Hg1—I1 | 100.74 (11) |
I1—Hg1—N1 | 98.91 (12) | N2i—Hg1—I2 | 100.93 (11) |
I2—Hg1—N1 | 103.46 (12) | N2i—Hg1—N1 | 86.14 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
(I) (X = Cl) | (II) (X = Br) | (III) (X = I) | |
Hg1—X2ii | 3.369 (4) | 3.625 (8) | 3.982 (4) |
X2—X2ii | 3.935 (5) | 4.077 (2) | 4.452 (5) |
X2—X1ii | 3.985 (3) | 4.405 (5) | 4.707 (2) |
X1—X1iii | 3.661 (4) | 3.913 (8) | 4.535 (4) |
Symmetry codes: (ii) -x-1, -y-1, -z+2; (iii) -x+1, -y, -z+2. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
Numerous supramolecular compounds designed and constructed through crystal engineering have attracted significant attention because of their fascinating structural topologies (Chae et al., 2001) and functional applications (Wang et al., 2011). It is well known that the selection of appropriate ligands as building blocks is a key point in the design and synthesis of functional supramolecular compounds. Compared with rigid ligands, flexible ligands can adopt different conformations under varying conditions resulting in potentially novel topologies (Chuang et al., 2010). N-donor ligands, such as those containing pyridyl groups, are good candidates for the assembly of versatile structures (Fujita et al., 2007). Recently, our group has reported several compounds generated from flexible ether-bridged ligands containing dicyanomethylene groups (Dong et al., 2007), carboxylic acid groups (Jiang et al., 2009) and terminal indoline-2,3-dione groups (Fang et al., 2011) and terminal imidazole groups (Yuan et al., 2011). There are few reports on flexible ether-bridged dipyridyl ligands. In order to investigate further the influence of factors such as the terminal groups of the ligand and the coordinated metal ions on the topologies and properties of supramolecular compounds, we studied the design and synthesis of a new flexible ether-bridged dipyridyl ligand 1,2-bis[4-(pyridin-3-yl)phenoxy]ethane (L). Three new macrocycles have been synthesized based on L and the inorganic salts HgX2 (X = Cl, Br and I), viz. [Hg2Cl4L2], (I), [Hg2Br4L2], (II), and [Hg2I4L2], (III). The X-ray crystal structures show that they are isostructural. We report the intermolecular interactions in the lattices of the three compounds.
The three isostructural compounds crystallize in the triclinic space group P1. The unit cells have been chosen in a similar fashion in order to facilitate the structural comparison. The unit cell of (III) became nonstandard (cell setting I, but b > c > a). As shown in Fig. 1, each compound contains macrocycles comprised of two ligands bridging two HgX2 moieties. The HgII centre lies in a highly distorted tetrahedral coordination environment defined by two N-atom donors from two pyridine ligands and two coordinated X- (X = Cl, Br and I). The corresponding metal–ligand interatomic bond distances and the bond angles exhibit some differences in (I), (II) and (III) (Tables 1–3), but are comparable to those of reported related HgII complexes (Masciocchi et al., 2009). The diameters of the cavities in the middle of the macrocycles are 3.269 (7), 3.811 (7) and 2.770 (6) Å for the Cl, Br and I derivatives, respectively.
The flexible L ligand can adopt different conformations under different conditions. In our previous study, the flexible ether-bridged organic ligand with terminal indoline-2,3-dione groups adopts a trans conformation about its central core in the free state, but a gauche conformation after coordinating to the AgI centre (Fang et al., 2011). Here in (I), the O1—C12—C13—O2 torsion angle of the central ether group is 108.5 (1)° (Fig. 1a). In (II), the torsion angle has changed to 109.9 (1)° (Fig. 1b), and in (III), the corresponding torsion angle is 77.9 (7)° (Fig. 1c). The sign of the torsion angle in (III) is opposite to that in (I) and (II), indicating a difference of some 150° between these torsion angles in the structures, so the ethylene bridge is oriented quite differently in (III) to the corresponding bridges in (I) and (II), as can be seen in Fig. 1. Additionally, the dihedral angle between the terminal N1-pyridine plane and the adjacent C6-benzene plane is 24.7 (2)° in (I) and 21.2 (2)° in (II). In contrast, the terminal N2-pyridine plane and the adjacent C17-benzene plane are nearly coplanar, with a dihedral angle of 9.8 (3)° in (I) and 6.8 (2)° in (II). In (III), the dihedral angles of the relative pyridine rings and benzene rings are 15.0 (2) and 18.5 (2)°.
In the solid state, as shown in Fig. 2, compounds (I)–(III) have the same packing motif. Herein, the representative structure of (I) is described in detail. As shown in Fig. 3, the one-dimensional Hg—Cl chains are formed along the [021] direction through noncovalent Hg···Cl interactions [Hg1···Cl2ii; symmetry code: (ii) -x+1, -y-1 -z+2]. If three different Cl···Cl interactions [Cl2···Cl1ii, Cl2···Cl2ii and Cl1···Cl1iii; symmetry code: ((iii) -x+1, -y, -z+2] are taken into consideration, a network parallel to the bc plane if formed. Fig. 4 shows the chains of Hg—Br moieties in (II) and the chains of Hg—I moieties in (III) with noncovalent interactions emphasized. The important noncovalent interactions in (I)–(III) are compared in Table 4. These two-dimensional sheets driven by noncovalent Hg···X and X···X (X = Cl, Br and I) interactions are both arranged in an ···AA··· parallel fashion in the a direction. The Hg—X distances, in the range 3.369 (2)–3.9819 (9) Å, are shorter than their van der Waals contact distances, the X···X distances are all beyond the sums of van der Waals radii (van der Waals radii: Hg = 2.15 Å, Cl = 1.80 Å, Br = 1.95 Å and I = 2.15 Å; Batsanov, 2001). Weak Cl···Cl interactions as long as 3.72 Å, which is longer than the van der Waals contact of 3.60 Å, have been reported for hexachlorobenzene (Sarma & Desiraju, 1986). The X···X (X = Cl, Br and I) distances in (I), (II) and (III) are a little longer than the sums of the van der Waals radii. The Hg—X and the weak X···X interactions are important for assisting in the lattice formation.
In summary, three macrocycles have been synthesized based on the flexible ether-bridged dipyridyl ligand. We anticipate this approach may be useful in constructing novel supramolecular compounds with the flexible ether-bridged dipyridyl ligand.