Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109025682/gd3293sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109025682/gd3293Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109025682/gd3293IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109025682/gd3293IIIasup4.hkl |
CCDC references: 746084; 746085; 746086
For related literature, see: Bleiholder et al. (2006, 2007); Bondi (1964); Gleiter & Werz (2005); Gleiter et al. (2003); Iwaoka et al. (2000, 2005); Iwaoka, Katsuda, Tomoda, Harada & Ogawa (2002); Iwaoka, Komatsu, Katsuda & Tomoda (2002); Kaur et al. (1996); Lari et al. (2009); Mundt et al. (2006); Nakanishi et al. (1998); Schulte et al. (2003); Tripathi et al. (2005); Werz et al. (2008); Werz et al. (2002a,b).
Compounds (I) and (II) were synthesized according to Iwaoka et al. (2005). Single crystals of (I) and (II) were obtained from a mixture of light petroleum and dichloromethane. The synthesis of (III) was carried out following the procedure described by Tripathi et al. (2005). Yellow crystals of (IIIa) crystallized in the triclinic space group P1.
H atoms were treated appropriate riding models for (I), (II), and (IIIa), except for the H atoms of the hydroxy groups of III a, which were refined isotropically. Both O–H distances refine to 0.74 (3) Å. Three reflections with very low Fobs, that were probably caught by the beam stop, were omitted for (I), and one such reflection was omitted for (II).
Data collection: SMART (Bruker, 2001) for (I); SMART (Bruker, 1995) for (II), (IIIa). Cell refinement: SAINT (Bruker, 2001) for (I); SAINT (Bruker, 1995) for (II), (IIIa). Data reduction: SAINT (Bruker, 2001) for (I); SAINT (Bruker, 1995) for (II), (IIIa). For all compounds, program(s) used to solve structure: SHELXTL (Sheldrick, 2008a); program(s) used to refine structure: SHELXTL (Sheldrick, 2008a); molecular graphics: SHELXTL (Sheldrick, 2008a); software used to prepare material for publication: SHELXTL (Sheldrick, 2008a).
C14H12Br2Se2 | F(000) = 1872 |
Mr = 497.98 | Dx = 2.157 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2113 reflections |
a = 11.4093 (11) Å | θ = 2.8–21.1° |
b = 11.3589 (11) Å | µ = 10.02 mm−1 |
c = 24.176 (2) Å | T = 296 K |
β = 101.861 (2)° | Polyhedron, yellow |
V = 3066.2 (5) Å3 | 0.13 × 0.11 × 0.04 mm |
Z = 8 |
Bruker APEX CCD diffractometer | 2811 independent reflections |
Radiation source: sealed tube | 1907 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.4°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | h = −13→13 |
Tmin = 0.346, Tmax = 0.670 | k = −13→13 |
12556 measured reflections | l = −29→29 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.033P)2 + 2.2551P] where P = (Fo2 + 2Fc2)/3 |
2811 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C14H12Br2Se2 | V = 3066.2 (5) Å3 |
Mr = 497.98 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 11.4093 (11) Å | µ = 10.02 mm−1 |
b = 11.3589 (11) Å | T = 296 K |
c = 24.176 (2) Å | 0.13 × 0.11 × 0.04 mm |
β = 101.861 (2)° |
Bruker APEX CCD diffractometer | 2811 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | 1907 reflections with I > 2σ(I) |
Tmin = 0.346, Tmax = 0.670 | Rint = 0.048 |
12556 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.58 e Å−3 |
2811 reflections | Δρmin = −0.46 e Å−3 |
163 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | ||
Se1 | 0.69989 (5) | 0.09986 (5) | 0.79237 (3) | 0.0709 (2) | |
Se2 | 0.66190 (5) | 0.16135 (6) | 0.69936 (2) | 0.0667 (2) | |
Br1 | 0.76165 (6) | 0.06700 (6) | 0.95336 (3) | 0.0796 (2) | |
Br2 | 0.59633 (6) | 0.20433 (6) | 0.54549 (3) | 0.0829 (2) | |
C11 | 0.8094 (4) | 0.2200 (4) | 0.8287 (2) | 0.0488 (12) | |
C12 | 0.8942 (4) | 0.2660 (4) | 0.8022 (2) | 0.0571 (14) | |
H12 | 0.9002 | 0.2389 | 0.7666 | 0.069* | |
C13 | 0.9706 (4) | 0.3525 (5) | 0.8282 (2) | 0.0609 (14) | |
H13 | 1.0277 | 0.3840 | 0.8100 | 0.073* | |
C14 | 0.9630 (5) | 0.3922 (5) | 0.8805 (3) | 0.0643 (15) | |
H14 | 1.0150 | 0.4504 | 0.8979 | 0.077* | |
C15 | 0.8788 (5) | 0.3461 (5) | 0.9073 (2) | 0.0593 (14) | |
H15 | 0.8738 | 0.3739 | 0.9429 | 0.071* | |
C16 | 0.8012 (4) | 0.2594 (4) | 0.8823 (2) | 0.0505 (12) | |
C17 | 0.7082 (5) | 0.2129 (5) | 0.9124 (2) | 0.0621 (15) | |
H17A | 0.6347 | 0.1980 | 0.8851 | 0.074* | |
H17B | 0.6916 | 0.2717 | 0.9388 | 0.074* | |
C21 | 0.7897 (4) | 0.0882 (4) | 0.6696 (2) | 0.0493 (12) | |
C22 | 0.8508 (5) | −0.0075 (5) | 0.6956 (2) | 0.0603 (14) | |
H22 | 0.8337 | −0.0370 | 0.7290 | 0.072* | |
C23 | 0.9383 (5) | −0.0599 (5) | 0.6716 (3) | 0.0684 (17) | |
H23 | 0.9795 | −0.1252 | 0.6888 | 0.082* | |
C24 | 0.9644 (5) | −0.0162 (6) | 0.6229 (3) | 0.0742 (18) | |
H24 | 1.0236 | −0.0512 | 0.6071 | 0.089* | |
C25 | 0.9029 (5) | 0.0795 (5) | 0.5973 (2) | 0.0658 (15) | |
H25 | 0.9205 | 0.1083 | 0.5640 | 0.079* | |
C26 | 0.8150 (4) | 0.1344 (5) | 0.6200 (2) | 0.0543 (13) | |
C27 | 0.7543 (5) | 0.2406 (5) | 0.5922 (2) | 0.0719 (16) | |
H27A | 0.8041 | 0.2759 | 0.5686 | 0.086* | |
H27B | 0.7450 | 0.2975 | 0.6209 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0735 (4) | 0.0786 (4) | 0.0668 (4) | −0.0331 (3) | 0.0289 (3) | −0.0171 (3) |
Se2 | 0.0494 (3) | 0.0867 (4) | 0.0625 (4) | 0.0136 (3) | 0.0081 (3) | −0.0183 (3) |
Br1 | 0.0979 (5) | 0.0742 (4) | 0.0716 (4) | −0.0073 (4) | 0.0287 (4) | 0.0099 (3) |
Br2 | 0.0640 (4) | 0.1060 (5) | 0.0743 (4) | 0.0093 (3) | 0.0042 (3) | 0.0123 (4) |
C11 | 0.044 (3) | 0.047 (3) | 0.056 (3) | −0.009 (2) | 0.013 (2) | −0.005 (2) |
C12 | 0.057 (3) | 0.059 (3) | 0.059 (3) | −0.008 (3) | 0.021 (3) | −0.009 (3) |
C13 | 0.046 (3) | 0.060 (4) | 0.077 (4) | −0.012 (3) | 0.014 (3) | 0.003 (3) |
C14 | 0.053 (3) | 0.055 (3) | 0.077 (4) | −0.008 (3) | −0.003 (3) | −0.014 (3) |
C15 | 0.059 (3) | 0.059 (3) | 0.055 (3) | 0.000 (3) | 0.000 (3) | −0.010 (3) |
C16 | 0.049 (3) | 0.057 (3) | 0.047 (3) | 0.006 (3) | 0.012 (2) | 0.001 (3) |
C17 | 0.061 (4) | 0.072 (4) | 0.055 (3) | 0.004 (3) | 0.016 (3) | −0.002 (3) |
C21 | 0.040 (3) | 0.052 (3) | 0.052 (3) | 0.001 (2) | 0.002 (2) | −0.017 (3) |
C22 | 0.051 (3) | 0.070 (4) | 0.058 (3) | 0.010 (3) | 0.006 (3) | −0.003 (3) |
C23 | 0.058 (4) | 0.058 (4) | 0.081 (5) | 0.012 (3) | −0.006 (3) | −0.014 (3) |
C24 | 0.050 (4) | 0.083 (4) | 0.092 (5) | 0.001 (3) | 0.020 (3) | −0.032 (4) |
C25 | 0.053 (3) | 0.082 (4) | 0.066 (4) | −0.007 (3) | 0.019 (3) | −0.019 (3) |
C26 | 0.046 (3) | 0.054 (3) | 0.061 (3) | −0.001 (2) | 0.008 (3) | −0.005 (3) |
C27 | 0.067 (4) | 0.071 (4) | 0.077 (4) | −0.011 (3) | 0.012 (3) | 0.001 (3) |
Se1—C11 | 1.935 (5) | C17—H17A | 0.9700 |
Se1—Se2 | 2.3090 (9) | C17—H17B | 0.9700 |
Se2—C21 | 1.941 (5) | C21—C22 | 1.373 (7) |
Br1—C17 | 1.963 (5) | C21—C26 | 1.391 (7) |
Br2—C27 | 1.964 (5) | C22—C23 | 1.388 (7) |
C11—C12 | 1.369 (6) | C22—H22 | 0.9300 |
C11—C16 | 1.394 (7) | C23—C24 | 1.366 (8) |
C12—C13 | 1.377 (7) | C23—H23 | 0.9300 |
C12—H12 | 0.9300 | C24—C25 | 1.370 (8) |
C13—C14 | 1.360 (7) | C24—H24 | 0.9300 |
C13—H13 | 0.9300 | C25—C26 | 1.386 (7) |
C14—C15 | 1.369 (7) | C25—H25 | 0.9300 |
C14—H14 | 0.9300 | C26—C27 | 1.482 (7) |
C15—C16 | 1.378 (7) | C27—H27A | 0.9700 |
C15—H15 | 0.9300 | C27—H27B | 0.9700 |
C16—C17 | 1.499 (7) | ||
C11—Se1—Se2 | 101.69 (15) | H17A—C17—H17B | 108.0 |
C21—Se2—Se1 | 103.12 (16) | C22—C21—C26 | 121.2 (5) |
C12—C11—C16 | 120.2 (5) | C22—C21—Se2 | 121.2 (4) |
C12—C11—Se1 | 120.7 (4) | C26—C21—Se2 | 117.6 (4) |
C16—C11—Se1 | 119.2 (4) | C21—C22—C23 | 119.3 (5) |
C11—C12—C13 | 120.0 (5) | C21—C22—H22 | 120.4 |
C11—C12—H12 | 120.0 | C23—C22—H22 | 120.4 |
C13—C12—H12 | 120.0 | C24—C23—C22 | 120.5 (5) |
C14—C13—C12 | 120.4 (5) | C24—C23—H23 | 119.7 |
C14—C13—H13 | 119.8 | C22—C23—H23 | 119.7 |
C12—C13—H13 | 119.8 | C23—C24—C25 | 119.7 (5) |
C13—C14—C15 | 119.9 (5) | C23—C24—H24 | 120.2 |
C13—C14—H14 | 120.1 | C25—C24—H24 | 120.2 |
C15—C14—H14 | 120.1 | C24—C25—C26 | 121.5 (6) |
C14—C15—C16 | 121.1 (5) | C24—C25—H25 | 119.2 |
C14—C15—H15 | 119.5 | C26—C25—H25 | 119.2 |
C16—C15—H15 | 119.5 | C25—C26—C21 | 117.8 (5) |
C15—C16—C11 | 118.5 (5) | C25—C26—C27 | 119.7 (5) |
C15—C16—C17 | 119.6 (5) | C21—C26—C27 | 122.5 (5) |
C11—C16—C17 | 121.9 (5) | C26—C27—Br2 | 112.3 (4) |
C16—C17—Br1 | 111.4 (3) | C26—C27—H27A | 109.2 |
C16—C17—H17A | 109.4 | Br2—C27—H27A | 109.2 |
Br1—C17—H17A | 109.4 | C26—C27—H27B | 109.2 |
C16—C17—H17B | 109.4 | Br2—C27—H27B | 109.2 |
Br1—C17—H17B | 109.4 | H27A—C27—H27B | 107.9 |
C11—Se1—Se2—C21 | 87.6 (2) | Se1—Se2—C21—C22 | 20.6 (4) |
Se2—Se1—C11—C12 | −37.8 (4) | Se1—Se2—C21—C26 | −161.1 (3) |
Se2—Se1—C11—C16 | 142.2 (4) | C26—C21—C22—C23 | −0.8 (7) |
C16—C11—C12—C13 | −0.8 (8) | Se2—C21—C22—C23 | 177.5 (4) |
Se1—C11—C12—C13 | 179.2 (4) | C21—C22—C23—C24 | 0.6 (8) |
C11—C12—C13—C14 | 0.5 (8) | C22—C23—C24—C25 | −0.5 (8) |
C12—C13—C14—C15 | −0.2 (8) | C23—C24—C25—C26 | 0.6 (8) |
C13—C14—C15—C16 | 0.3 (8) | C24—C25—C26—C21 | −0.8 (8) |
C14—C15—C16—C11 | −0.7 (8) | C24—C25—C26—C27 | 177.5 (5) |
C14—C15—C16—C17 | −178.6 (5) | C22—C21—C26—C25 | 0.9 (7) |
C12—C11—C16—C15 | 0.9 (7) | Se2—C21—C26—C25 | −177.4 (4) |
Se1—C11—C16—C15 | −179.1 (4) | C22—C21—C26—C27 | −177.4 (5) |
C12—C11—C16—C17 | 178.8 (5) | Se2—C21—C26—C27 | 4.3 (6) |
Se1—C11—C16—C17 | −1.2 (7) | C25—C26—C27—Br2 | 100.3 (5) |
C15—C16—C17—Br1 | −97.0 (5) | C21—C26—C27—Br2 | −81.5 (6) |
C11—C16—C17—Br1 | 85.1 (5) |
C14H12Cl2Se2 | Z = 4 |
Mr = 409.06 | F(000) = 792 |
Triclinic, P1 | Dx = 1.851 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9160 (2) Å | Cell parameters from 5803 reflections |
b = 8.0215 (1) Å | θ = 1.8–23.0° |
c = 23.4689 (4) Å | µ = 5.38 mm−1 |
α = 98.388 (1)° | T = 200 K |
β = 95.287 (1)° | Platte, yellow |
γ = 90.610 (1)° | 0.21 × 0.20 × 0.06 mm |
V = 1467.58 (5) Å3 |
Bruker SMART CCD diffractometer | 6651 independent reflections |
Radiation source: sealed tube | 4403 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 27.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | h = −10→10 |
Tmin = 0.390, Tmax = 0.724 | k = −10→10 |
14837 measured reflections | l = −30→30 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0308P)2] where P = (Fo2 + 2Fc2)/3 |
6651 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
C14H12Cl2Se2 | γ = 90.610 (1)° |
Mr = 409.06 | V = 1467.58 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.9160 (2) Å | Mo Kα radiation |
b = 8.0215 (1) Å | µ = 5.38 mm−1 |
c = 23.4689 (4) Å | T = 200 K |
α = 98.388 (1)° | 0.21 × 0.20 × 0.06 mm |
β = 95.287 (1)° |
Bruker SMART CCD diffractometer | 6651 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | 4403 reflections with I > 2σ(I) |
Tmin = 0.390, Tmax = 0.724 | Rint = 0.056 |
14837 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.49 e Å−3 |
6651 reflections | Δρmin = −0.51 e Å−3 |
325 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 | ||
Se1A | 0.02252 (6) | 0.35676 (7) | 0.19834 (2) | 0.03901 (14) | |
Se2A | 0.13781 (7) | 0.47430 (6) | 0.28967 (2) | 0.04203 (15) | |
Cl1A | −0.09164 (17) | 0.24958 (19) | 0.04805 (6) | 0.0543 (4) | |
Cl2A | 0.20042 (18) | 0.60849 (17) | 0.44710 (6) | 0.0523 (4) | |
C11A | 0.2160 (5) | 0.2568 (6) | 0.1628 (2) | 0.0301 (11) | |
C12A | 0.3819 (6) | 0.2981 (6) | 0.1857 (2) | 0.0407 (12) | |
H12A | 0.4034 | 0.3739 | 0.2208 | 0.049* | |
C13A | 0.5159 (6) | 0.2280 (7) | 0.1571 (2) | 0.0456 (14) | |
H13A | 0.6291 | 0.2564 | 0.1728 | 0.055* | |
C14A | 0.4872 (6) | 0.1179 (7) | 0.1062 (2) | 0.0460 (14) | |
H14A | 0.5799 | 0.0703 | 0.0871 | 0.055* | |
C15A | 0.3223 (6) | 0.0774 (6) | 0.0833 (2) | 0.0415 (13) | |
H15A | 0.3020 | 0.0028 | 0.0479 | 0.050* | |
C16A | 0.1853 (6) | 0.1443 (6) | 0.1114 (2) | 0.0327 (11) | |
C17A | 0.0095 (6) | 0.0901 (7) | 0.0864 (2) | 0.0435 (13) | |
H17A | −0.0591 | 0.0685 | 0.1178 | 0.052* | |
H17B | 0.0139 | −0.0164 | 0.0593 | 0.052* | |
C21A | 0.1105 (5) | 0.2876 (6) | 0.33259 (19) | 0.0289 (10) | |
C22A | 0.1474 (6) | 0.1258 (6) | 0.3081 (2) | 0.0351 (11) | |
H22A | 0.1873 | 0.1068 | 0.2707 | 0.042* | |
C23A | 0.1261 (6) | −0.0078 (6) | 0.3380 (2) | 0.0381 (12) | |
H23A | 0.1514 | −0.1188 | 0.3214 | 0.046* | |
C24A | 0.0678 (6) | 0.0204 (6) | 0.3924 (2) | 0.0403 (12) | |
H24A | 0.0526 | −0.0717 | 0.4128 | 0.048* | |
C25A | 0.0315 (6) | 0.1814 (6) | 0.4170 (2) | 0.0361 (12) | |
H25A | −0.0081 | 0.1994 | 0.4544 | 0.043* | |
C26A | 0.0525 (5) | 0.3181 (6) | 0.3875 (2) | 0.0292 (10) | |
C27A | 0.0092 (6) | 0.4921 (6) | 0.4144 (2) | 0.0375 (12) | |
H27A | −0.0699 | 0.4842 | 0.4443 | 0.045* | |
H27B | −0.0479 | 0.5525 | 0.3844 | 0.045* | |
Se1B | 0.68828 (7) | 0.77512 (6) | 0.30381 (2) | 0.03980 (15) | |
Se2B | 0.71591 (6) | 0.76686 (7) | 0.20615 (2) | 0.04104 (15) | |
Cl1B | 0.68193 (18) | 0.82519 (19) | 0.45300 (6) | 0.0540 (4) | |
Cl2B | 0.69297 (17) | 0.70381 (17) | 0.04715 (6) | 0.0483 (3) | |
C11B | 0.6416 (5) | 1.0089 (5) | 0.3296 (2) | 0.0291 (10) | |
C12B | 0.6884 (6) | 1.1366 (6) | 0.2988 (2) | 0.0365 (12) | |
H12B | 0.7418 | 1.1099 | 0.2641 | 0.044* | |
C13B | 0.6549 (6) | 1.3042 (6) | 0.3201 (2) | 0.0426 (13) | |
H13B | 0.6840 | 1.3916 | 0.2992 | 0.051* | |
C14B | 0.5808 (6) | 1.3432 (6) | 0.3706 (2) | 0.0444 (13) | |
H14B | 0.5617 | 1.4576 | 0.3851 | 0.053* | |
C15B | 0.5337 (6) | 1.2169 (6) | 0.4006 (2) | 0.0417 (13) | |
H15B | 0.4808 | 1.2453 | 0.4353 | 0.050* | |
C16B | 0.5628 (6) | 1.0478 (6) | 0.3805 (2) | 0.0324 (11) | |
C17B | 0.5059 (6) | 0.9132 (7) | 0.4134 (2) | 0.0428 (13) | |
H17C | 0.4451 | 0.8220 | 0.3860 | 0.051* | |
H17D | 0.4255 | 0.9618 | 0.4409 | 0.051* | |
C21B | 0.4835 (5) | 0.7380 (6) | 0.1730 (2) | 0.0296 (10) | |
C22B | 0.3531 (6) | 0.8109 (6) | 0.2016 (2) | 0.0339 (11) | |
H22B | 0.3775 | 0.8778 | 0.2384 | 0.041* | |
C23B | 0.1868 (6) | 0.7887 (6) | 0.1776 (2) | 0.0395 (12) | |
H23B | 0.0974 | 0.8383 | 0.1981 | 0.047* | |
C24B | 0.1515 (6) | 0.6931 (6) | 0.1233 (2) | 0.0413 (13) | |
H24B | 0.0376 | 0.6774 | 0.1064 | 0.050* | |
C25B | 0.2825 (6) | 0.6210 (6) | 0.0942 (2) | 0.0388 (12) | |
H25B | 0.2574 | 0.5563 | 0.0570 | 0.047* | |
C26B | 0.4505 (6) | 0.6412 (6) | 0.1179 (2) | 0.0300 (11) | |
C27B | 0.5867 (6) | 0.5579 (6) | 0.0850 (2) | 0.0389 (12) | |
H27C | 0.5364 | 0.4627 | 0.0566 | 0.047* | |
H27D | 0.6708 | 0.5117 | 0.1120 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1A | 0.0349 (3) | 0.0478 (3) | 0.0358 (3) | 0.0118 (2) | 0.0053 (2) | 0.0090 (2) |
Se2A | 0.0623 (4) | 0.0267 (3) | 0.0375 (3) | 0.0023 (2) | 0.0091 (3) | 0.0032 (2) |
Cl1A | 0.0450 (8) | 0.0666 (10) | 0.0486 (9) | 0.0124 (7) | −0.0071 (6) | 0.0058 (7) |
Cl2A | 0.0594 (9) | 0.0407 (8) | 0.0529 (9) | −0.0092 (7) | 0.0060 (7) | −0.0058 (7) |
C11A | 0.027 (2) | 0.034 (3) | 0.033 (3) | 0.000 (2) | 0.004 (2) | 0.015 (2) |
C12A | 0.040 (3) | 0.041 (3) | 0.042 (3) | 0.001 (2) | 0.004 (2) | 0.009 (2) |
C13A | 0.025 (3) | 0.060 (4) | 0.057 (4) | 0.001 (2) | 0.002 (2) | 0.026 (3) |
C14A | 0.037 (3) | 0.056 (4) | 0.052 (4) | 0.016 (3) | 0.019 (3) | 0.022 (3) |
C15A | 0.047 (3) | 0.043 (3) | 0.038 (3) | 0.009 (3) | 0.012 (3) | 0.011 (3) |
C16A | 0.037 (3) | 0.032 (3) | 0.033 (3) | 0.002 (2) | 0.004 (2) | 0.013 (2) |
C17A | 0.039 (3) | 0.053 (3) | 0.038 (3) | −0.004 (3) | −0.003 (2) | 0.007 (3) |
C21A | 0.031 (3) | 0.027 (3) | 0.028 (3) | 0.003 (2) | 0.001 (2) | 0.005 (2) |
C22A | 0.034 (3) | 0.032 (3) | 0.039 (3) | 0.007 (2) | 0.008 (2) | 0.001 (2) |
C23A | 0.038 (3) | 0.022 (3) | 0.053 (4) | 0.002 (2) | 0.000 (3) | 0.007 (2) |
C24A | 0.039 (3) | 0.036 (3) | 0.048 (3) | 0.004 (2) | 0.001 (2) | 0.018 (3) |
C25A | 0.032 (3) | 0.045 (3) | 0.032 (3) | 0.004 (2) | 0.000 (2) | 0.008 (2) |
C26A | 0.026 (2) | 0.030 (3) | 0.030 (3) | 0.005 (2) | −0.002 (2) | 0.001 (2) |
C27A | 0.040 (3) | 0.041 (3) | 0.031 (3) | 0.005 (2) | 0.007 (2) | 0.000 (2) |
Se1B | 0.0517 (3) | 0.0272 (3) | 0.0367 (3) | 0.0092 (2) | −0.0087 (2) | −0.0008 (2) |
Se2B | 0.0255 (3) | 0.0530 (3) | 0.0389 (3) | 0.0042 (2) | 0.0017 (2) | −0.0116 (3) |
Cl1B | 0.0565 (9) | 0.0628 (9) | 0.0477 (9) | 0.0171 (7) | 0.0076 (7) | 0.0223 (7) |
Cl2B | 0.0480 (8) | 0.0542 (9) | 0.0431 (8) | −0.0032 (7) | 0.0135 (6) | 0.0027 (6) |
C11B | 0.032 (3) | 0.021 (2) | 0.032 (3) | 0.0024 (19) | −0.011 (2) | 0.002 (2) |
C12B | 0.034 (3) | 0.036 (3) | 0.037 (3) | −0.001 (2) | −0.004 (2) | 0.004 (2) |
C13B | 0.044 (3) | 0.034 (3) | 0.048 (3) | 0.000 (2) | −0.012 (3) | 0.009 (3) |
C14B | 0.040 (3) | 0.030 (3) | 0.058 (4) | 0.003 (2) | −0.006 (3) | −0.004 (3) |
C15B | 0.033 (3) | 0.045 (3) | 0.043 (3) | 0.004 (2) | 0.004 (2) | −0.010 (3) |
C16B | 0.028 (2) | 0.032 (3) | 0.034 (3) | 0.005 (2) | −0.004 (2) | −0.001 (2) |
C17B | 0.039 (3) | 0.050 (3) | 0.042 (3) | 0.005 (2) | 0.006 (2) | 0.014 (3) |
C21B | 0.026 (2) | 0.031 (3) | 0.031 (3) | −0.001 (2) | 0.001 (2) | 0.003 (2) |
C22B | 0.031 (3) | 0.031 (3) | 0.038 (3) | 0.004 (2) | 0.005 (2) | −0.001 (2) |
C23B | 0.026 (3) | 0.043 (3) | 0.051 (3) | 0.001 (2) | 0.010 (2) | 0.007 (3) |
C24B | 0.031 (3) | 0.044 (3) | 0.048 (3) | −0.006 (2) | −0.008 (2) | 0.010 (3) |
C25B | 0.045 (3) | 0.036 (3) | 0.034 (3) | −0.004 (2) | −0.007 (2) | 0.006 (2) |
C26B | 0.034 (3) | 0.028 (3) | 0.029 (3) | 0.001 (2) | 0.004 (2) | 0.006 (2) |
C27B | 0.050 (3) | 0.035 (3) | 0.030 (3) | −0.001 (2) | 0.002 (2) | 0.001 (2) |
Se1A—C11A | 1.937 (4) | Se1B—C11B | 1.935 (4) |
Se1A—Se2A | 2.3124 (8) | Se1B—Se2B | 2.3140 (8) |
Se2A—C21A | 1.944 (4) | Se2B—C21B | 1.928 (4) |
Cl1A—C17A | 1.819 (5) | Cl1B—C17B | 1.810 (5) |
Cl2A—C27A | 1.816 (5) | Cl2B—C27B | 1.813 (5) |
C11A—C12A | 1.391 (6) | C11B—C16B | 1.396 (6) |
C11A—C16A | 1.397 (7) | C11B—C12B | 1.402 (6) |
C12A—C13A | 1.389 (7) | C12B—C13B | 1.401 (7) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.376 (8) | C13B—C14B | 1.368 (7) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C15A | 1.383 (7) | C14B—C15B | 1.382 (7) |
C14A—H14A | 0.9500 | C14B—H14B | 0.9500 |
C15A—C16A | 1.392 (6) | C15B—C16B | 1.398 (6) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.494 (7) | C16B—C17B | 1.504 (7) |
C17A—H17A | 0.9900 | C17B—H17C | 0.9900 |
C17A—H17B | 0.9900 | C17B—H17D | 0.9900 |
C21A—C22A | 1.387 (6) | C21B—C22B | 1.372 (6) |
C21A—C26A | 1.397 (6) | C21B—C26B | 1.409 (6) |
C22A—C23A | 1.382 (6) | C22B—C23B | 1.382 (6) |
C22A—H22A | 0.9500 | C22B—H22B | 0.9500 |
C23A—C24A | 1.385 (7) | C23B—C24B | 1.391 (7) |
C23A—H23A | 0.9500 | C23B—H23B | 0.9500 |
C24A—C25A | 1.381 (7) | C24B—C25B | 1.381 (7) |
C24A—H24A | 0.9500 | C24B—H24B | 0.9500 |
C25A—C26A | 1.396 (6) | C25B—C26B | 1.393 (6) |
C25A—H25A | 0.9500 | C25B—H25B | 0.9500 |
C26A—C27A | 1.502 (6) | C26B—C27B | 1.491 (6) |
C27A—H27A | 0.9900 | C27B—H27C | 0.9900 |
C27A—H27B | 0.9900 | C27B—H27D | 0.9900 |
C11A—Se1A—Se2A | 103.20 (14) | C11B—Se1B—Se2B | 103.60 (14) |
C21A—Se2A—Se1A | 100.96 (14) | C21B—Se2B—Se1B | 102.10 (14) |
C12A—C11A—C16A | 119.9 (4) | C16B—C11B—C12B | 120.7 (4) |
C12A—C11A—Se1A | 122.1 (4) | C16B—C11B—Se1B | 118.1 (3) |
C16A—C11A—Se1A | 118.1 (3) | C12B—C11B—Se1B | 121.2 (4) |
C13A—C12A—C11A | 119.6 (5) | C13B—C12B—C11B | 118.8 (5) |
C13A—C12A—H12A | 120.2 | C13B—C12B—H12B | 120.6 |
C11A—C12A—H12A | 120.2 | C11B—C12B—H12B | 120.6 |
C14A—C13A—C12A | 121.1 (5) | C14B—C13B—C12B | 120.7 (5) |
C14A—C13A—H13A | 119.5 | C14B—C13B—H13B | 119.7 |
C12A—C13A—H13A | 119.5 | C12B—C13B—H13B | 119.7 |
C13A—C14A—C15A | 119.3 (5) | C13B—C14B—C15B | 120.3 (5) |
C13A—C14A—H14A | 120.3 | C13B—C14B—H14B | 119.9 |
C15A—C14A—H14A | 120.3 | C15B—C14B—H14B | 119.9 |
C14A—C15A—C16A | 120.9 (5) | C14B—C15B—C16B | 120.9 (5) |
C14A—C15A—H15A | 119.5 | C14B—C15B—H15B | 119.6 |
C16A—C15A—H15A | 119.5 | C16B—C15B—H15B | 119.6 |
C15A—C16A—C11A | 119.2 (5) | C11B—C16B—C15B | 118.6 (4) |
C15A—C16A—C17A | 118.9 (5) | C11B—C16B—C17B | 121.9 (4) |
C11A—C16A—C17A | 121.9 (4) | C15B—C16B—C17B | 119.5 (5) |
C16A—C17A—Cl1A | 111.5 (3) | C16B—C17B—Cl1B | 112.2 (3) |
C16A—C17A—H17A | 109.3 | C16B—C17B—H17C | 109.2 |
Cl1A—C17A—H17A | 109.3 | Cl1B—C17B—H17C | 109.2 |
C16A—C17A—H17B | 109.3 | C16B—C17B—H17D | 109.2 |
Cl1A—C17A—H17B | 109.3 | Cl1B—C17B—H17D | 109.2 |
H17A—C17A—H17B | 108.0 | H17C—C17B—H17D | 107.9 |
C22A—C21A—C26A | 120.9 (4) | C22B—C21B—C26B | 120.4 (4) |
C22A—C21A—Se2A | 119.5 (3) | C22B—C21B—Se2B | 121.5 (4) |
C26A—C21A—Se2A | 119.5 (3) | C26B—C21B—Se2B | 118.1 (3) |
C23A—C22A—C21A | 119.8 (5) | C21B—C22B—C23B | 121.0 (5) |
C23A—C22A—H22A | 120.1 | C21B—C22B—H22B | 119.5 |
C21A—C22A—H22A | 120.1 | C23B—C22B—H22B | 119.5 |
C22A—C23A—C24A | 119.9 (5) | C22B—C23B—C24B | 119.5 (5) |
C22A—C23A—H23A | 120.0 | C22B—C23B—H23B | 120.3 |
C24A—C23A—H23A | 120.0 | C24B—C23B—H23B | 120.3 |
C25A—C24A—C23A | 120.4 (5) | C25B—C24B—C23B | 119.7 (5) |
C25A—C24A—H24A | 119.8 | C25B—C24B—H24B | 120.1 |
C23A—C24A—H24A | 119.8 | C23B—C24B—H24B | 120.1 |
C24A—C25A—C26A | 120.5 (5) | C24B—C25B—C26B | 121.5 (5) |
C24A—C25A—H25A | 119.7 | C24B—C25B—H25B | 119.2 |
C26A—C25A—H25A | 119.7 | C26B—C25B—H25B | 119.2 |
C25A—C26A—C21A | 118.4 (4) | C25B—C26B—C21B | 117.9 (4) |
C25A—C26A—C27A | 119.9 (4) | C25B—C26B—C27B | 119.2 (4) |
C21A—C26A—C27A | 121.7 (4) | C21B—C26B—C27B | 122.9 (4) |
C26A—C27A—Cl2A | 110.2 (3) | C26B—C27B—Cl2B | 111.6 (3) |
C26A—C27A—H27A | 109.6 | C26B—C27B—H27C | 109.3 |
Cl2A—C27A—H27A | 109.6 | Cl2B—C27B—H27C | 109.3 |
C26A—C27A—H27B | 109.6 | C26B—C27B—H27D | 109.3 |
Cl2A—C27A—H27B | 109.6 | Cl2B—C27B—H27D | 109.3 |
H27A—C27A—H27B | 108.1 | H27C—C27B—H27D | 108.0 |
C11A—Se1A—Se2A—C21A | −90.15 (19) | C11B—Se1B—Se2B—C21B | −85.08 (19) |
Se2A—Se1A—C11A—C12A | −15.4 (4) | Se2B—Se1B—C11B—C16B | 158.7 (3) |
Se2A—Se1A—C11A—C16A | 166.7 (3) | Se2B—Se1B—C11B—C12B | −22.5 (4) |
C16A—C11A—C12A—C13A | 0.5 (7) | C16B—C11B—C12B—C13B | 0.2 (7) |
Se1A—C11A—C12A—C13A | −177.3 (4) | Se1B—C11B—C12B—C13B | −178.6 (3) |
C11A—C12A—C13A—C14A | 0.0 (8) | C11B—C12B—C13B—C14B | 1.2 (7) |
C12A—C13A—C14A—C15A | 0.3 (8) | C12B—C13B—C14B—C15B | −1.7 (8) |
C13A—C14A—C15A—C16A | −1.0 (8) | C13B—C14B—C15B—C16B | 1.0 (8) |
C14A—C15A—C16A—C11A | 1.4 (7) | C12B—C11B—C16B—C15B | −0.9 (7) |
C14A—C15A—C16A—C17A | −177.1 (4) | Se1B—C11B—C16B—C15B | 177.9 (3) |
C12A—C11A—C16A—C15A | −1.2 (7) | C12B—C11B—C16B—C17B | 177.9 (4) |
Se1A—C11A—C16A—C15A | 176.7 (3) | Se1B—C11B—C16B—C17B | −3.3 (6) |
C12A—C11A—C16A—C17A | 177.3 (4) | C14B—C15B—C16B—C11B | 0.4 (7) |
Se1A—C11A—C16A—C17A | −4.9 (6) | C14B—C15B—C16B—C17B | −178.5 (4) |
C15A—C16A—C17A—Cl1A | −102.3 (5) | C11B—C16B—C17B—Cl1B | 75.0 (5) |
C11A—C16A—C17A—Cl1A | 79.3 (5) | C15B—C16B—C17B—Cl1B | −106.2 (5) |
Se1A—Se2A—C21A—C22A | 42.9 (4) | Se1B—Se2B—C21B—C22B | 34.6 (4) |
Se1A—Se2A—C21A—C26A | −136.5 (3) | Se1B—Se2B—C21B—C26B | −146.2 (3) |
C26A—C21A—C22A—C23A | 0.3 (7) | C26B—C21B—C22B—C23B | 1.3 (7) |
Se2A—C21A—C22A—C23A | −179.1 (4) | Se2B—C21B—C22B—C23B | −179.6 (4) |
C21A—C22A—C23A—C24A | 0.1 (7) | C21B—C22B—C23B—C24B | −1.0 (7) |
C22A—C23A—C24A—C25A | −0.3 (7) | C22B—C23B—C24B—C25B | 0.3 (7) |
C23A—C24A—C25A—C26A | 0.2 (7) | C23B—C24B—C25B—C26B | 0.2 (7) |
C24A—C25A—C26A—C21A | 0.1 (7) | C24B—C25B—C26B—C21B | 0.0 (7) |
C24A—C25A—C26A—C27A | 178.8 (4) | C24B—C25B—C26B—C27B | 178.9 (4) |
C22A—C21A—C26A—C25A | −0.4 (7) | C22B—C21B—C26B—C25B | −0.7 (7) |
Se2A—C21A—C26A—C25A | 179.0 (3) | Se2B—C21B—C26B—C25B | −179.9 (3) |
C22A—C21A—C26A—C27A | −179.0 (4) | C22B—C21B—C26B—C27B | −179.6 (4) |
Se2A—C21A—C26A—C27A | 0.4 (6) | Se2B—C21B—C26B—C27B | 1.3 (6) |
C25A—C26A—C27A—Cl2A | 99.6 (4) | C25B—C26B—C27B—Cl2B | 99.3 (4) |
C21A—C26A—C27A—Cl2A | −81.8 (5) | C21B—C26B—C27B—Cl2B | −81.8 (5) |
C14H14O2Se2 | Z = 2 |
Mr = 372.17 | F(000) = 364 |
Triclinic, P1 | Dx = 1.829 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4461 (2) Å | Cell parameters from 4727 reflections |
b = 8.9003 (3) Å | θ = 2.2–21.0° |
c = 9.7427 (3) Å | µ = 5.46 mm−1 |
α = 72.904 (1)° | T = 200 K |
β = 78.950 (1)° | Polyhedron, yellow |
γ = 76.978 (1)° | 0.24 × 0.16 × 0.10 mm |
V = 675.81 (4) Å3 |
Bruker SMART CCD diffractometer | 3051 independent reflections |
Radiation source: sealed tube | 2667 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | h = −10→10 |
Tmin = 0.336, Tmax = 0.581 | k = −11→11 |
6951 measured reflections | l = −12→12 |
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) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0361P)2 + 0.1634P] where P = (Fo2 + 2Fc2)/3 |
3051 reflections | (Δ/σ)max = 0.001 |
171 parameters | Δρmax = 0.60 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C14H14O2Se2 | γ = 76.978 (1)° |
Mr = 372.17 | V = 675.81 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4461 (2) Å | Mo Kα radiation |
b = 8.9003 (3) Å | µ = 5.46 mm−1 |
c = 9.7427 (3) Å | T = 200 K |
α = 72.904 (1)° | 0.24 × 0.16 × 0.10 mm |
β = 78.950 (1)° |
Bruker SMART CCD diffractometer | 3051 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b) | 2667 reflections with I > 2σ(I) |
Tmin = 0.336, Tmax = 0.581 | Rint = 0.029 |
6951 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.60 e Å−3 |
3051 reflections | Δρmin = −0.52 e Å−3 |
171 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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | ||
Se1 | 0.32970 (3) | 0.83372 (3) | 0.42870 (2) | 0.02635 (9) | |
Se2 | 0.09747 (3) | 0.97156 (3) | 0.31659 (2) | 0.02662 (9) | |
O1 | 0.0427 (3) | 0.4895 (2) | 0.7814 (2) | 0.0342 (4) | |
O2 | 0.1712 (3) | 1.3434 (2) | 0.0417 (2) | 0.0379 (5) | |
H2 | 0.149 (5) | 1.374 (5) | −0.033 (4) | 0.059 (13)* | |
C11 | 0.3137 (3) | 0.6194 (3) | 0.4352 (2) | 0.0234 (5) | |
C12 | 0.4015 (3) | 0.5537 (3) | 0.3245 (3) | 0.0300 (6) | |
H12 | 0.4678 | 0.6146 | 0.2479 | 0.036* | |
C13 | 0.3932 (3) | 0.4003 (3) | 0.3251 (3) | 0.0375 (7) | |
H13 | 0.4535 | 0.3557 | 0.2491 | 0.045* | |
C14 | 0.2973 (3) | 0.3125 (3) | 0.4361 (3) | 0.0357 (6) | |
H14 | 0.2921 | 0.2069 | 0.4366 | 0.043* | |
C15 | 0.2078 (3) | 0.3768 (3) | 0.5477 (3) | 0.0293 (5) | |
H15 | 0.1410 | 0.3151 | 0.6230 | 0.035* | |
C16 | 0.2153 (3) | 0.5299 (3) | 0.5500 (2) | 0.0224 (5) | |
C17 | 0.1211 (3) | 0.6030 (3) | 0.6692 (3) | 0.0299 (5) | |
H17A | 0.1969 | 0.6431 | 0.7101 | 0.036* | |
H17B | 0.0375 | 0.6950 | 0.6288 | 0.036* | |
C21 | 0.1801 (3) | 0.9551 (3) | 0.1218 (2) | 0.0228 (5) | |
C22 | 0.1505 (3) | 0.8264 (3) | 0.0839 (3) | 0.0289 (5) | |
H22 | 0.0948 | 0.7494 | 0.1537 | 0.035* | |
C23 | 0.2023 (3) | 0.8097 (3) | −0.0559 (3) | 0.0361 (6) | |
H23 | 0.1832 | 0.7210 | −0.0816 | 0.043* | |
C24 | 0.2818 (3) | 0.9230 (4) | −0.1574 (3) | 0.0367 (7) | |
H24 | 0.3152 | 0.9134 | −0.2537 | 0.044* | |
C25 | 0.3128 (3) | 1.0502 (3) | −0.1191 (3) | 0.0312 (6) | |
H25 | 0.3687 | 1.1265 | −0.1897 | 0.037* | |
C26 | 0.2637 (3) | 1.0691 (3) | 0.0212 (2) | 0.0235 (5) | |
C27 | 0.3022 (3) | 1.2092 (3) | 0.0571 (3) | 0.0310 (6) | |
H27A | 0.3269 | 1.1758 | 0.1582 | 0.037* | |
H27B | 0.4015 | 1.2415 | −0.0072 | 0.037* | |
H1 | −0.022 (4) | 0.540 (4) | 0.819 (3) | 0.036 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.03383 (15) | 0.02426 (14) | 0.02238 (13) | −0.00941 (11) | −0.00424 (10) | −0.00485 (10) |
Se2 | 0.03208 (15) | 0.02168 (14) | 0.02143 (13) | −0.00077 (10) | 0.00146 (10) | −0.00489 (10) |
O1 | 0.0405 (11) | 0.0269 (10) | 0.0270 (10) | −0.0066 (9) | 0.0078 (8) | −0.0019 (8) |
O2 | 0.0521 (13) | 0.0267 (10) | 0.0314 (11) | 0.0019 (9) | −0.0067 (9) | −0.0082 (8) |
C11 | 0.0276 (12) | 0.0205 (11) | 0.0225 (11) | −0.0008 (10) | −0.0080 (9) | −0.0060 (9) |
C12 | 0.0303 (13) | 0.0370 (14) | 0.0228 (12) | −0.0042 (11) | −0.0015 (10) | −0.0105 (10) |
C13 | 0.0395 (15) | 0.0384 (16) | 0.0397 (15) | 0.0066 (13) | −0.0110 (12) | −0.0246 (13) |
C14 | 0.0417 (15) | 0.0255 (13) | 0.0458 (16) | 0.0011 (12) | −0.0137 (13) | −0.0185 (12) |
C15 | 0.0335 (13) | 0.0212 (12) | 0.0340 (13) | −0.0045 (10) | −0.0079 (11) | −0.0064 (10) |
C16 | 0.0249 (11) | 0.0212 (11) | 0.0209 (11) | −0.0012 (9) | −0.0060 (9) | −0.0057 (9) |
C17 | 0.0386 (14) | 0.0267 (13) | 0.0242 (12) | −0.0090 (11) | 0.0024 (10) | −0.0081 (10) |
C21 | 0.0246 (12) | 0.0214 (12) | 0.0209 (11) | −0.0008 (9) | −0.0041 (9) | −0.0050 (9) |
C22 | 0.0304 (13) | 0.0254 (13) | 0.0310 (13) | −0.0068 (10) | −0.0043 (10) | −0.0062 (10) |
C23 | 0.0377 (15) | 0.0376 (15) | 0.0407 (15) | −0.0031 (12) | −0.0103 (12) | −0.0213 (13) |
C24 | 0.0349 (14) | 0.0494 (17) | 0.0261 (13) | 0.0055 (13) | −0.0065 (11) | −0.0188 (12) |
C25 | 0.0271 (13) | 0.0381 (15) | 0.0237 (12) | −0.0018 (11) | −0.0015 (10) | −0.0052 (11) |
C26 | 0.0209 (11) | 0.0237 (12) | 0.0227 (11) | −0.0001 (9) | −0.0042 (9) | −0.0033 (9) |
C27 | 0.0310 (13) | 0.0280 (14) | 0.0326 (14) | −0.0076 (11) | −0.0036 (11) | −0.0048 (11) |
Se1—C11 | 1.924 (2) | C15—C16 | 1.385 (3) |
Se1—Se2 | 2.3441 (3) | C15—H15 | 0.9500 |
Se2—C21 | 1.929 (2) | C16—C17 | 1.504 (3) |
Se2—Se2i | 3.7646 (5) | C17—H17A | 0.9900 |
Se2—H17Bi | 3.0920 | C17—H17B | 0.9900 |
O1—O2i | 2.747 (3) | C21—C22 | 1.387 (3) |
O1—O2ii | 2.790 (3) | C21—C26 | 1.400 (3) |
O1—C17 | 1.424 (3) | C22—C23 | 1.389 (4) |
O1—H1 | 0.74 (3) | C22—H22 | 0.9500 |
O2—C27 | 1.427 (3) | C23—C24 | 1.382 (4) |
O2—H2 | 0.74 (4) | C23—H23 | 0.9500 |
C11—C12 | 1.387 (3) | C24—C25 | 1.381 (4) |
C11—C16 | 1.413 (3) | C24—H24 | 0.9500 |
C12—C13 | 1.381 (4) | C25—C26 | 1.399 (3) |
C12—H12 | 0.9500 | C25—H25 | 0.9500 |
C13—C14 | 1.375 (4) | C26—C27 | 1.505 (4) |
C13—H13 | 0.9500 | C27—H27A | 0.9900 |
C14—C15 | 1.392 (4) | C27—H27B | 0.9900 |
C14—H14 | 0.9500 | ||
C11—Se1—Se2 | 98.92 (7) | C16—C17—H17B | 109.4 |
C21—Se2—Se1 | 99.06 (7) | H17A—C17—H17B | 108.0 |
C21—Se2—Se2i | 174.82 (7) | C22—C21—C26 | 121.0 (2) |
C17—O1—H1 | 103 (3) | C22—C21—Se2 | 117.09 (18) |
C27—O2—H2 | 113 (3) | C26—C21—Se2 | 121.91 (17) |
C12—C11—C16 | 120.3 (2) | C21—C22—C23 | 120.1 (2) |
C12—C11—Se1 | 118.61 (19) | C21—C22—H22 | 119.9 |
C16—C11—Se1 | 121.07 (17) | C23—C22—H22 | 119.9 |
C13—C12—C11 | 120.4 (2) | C24—C23—C22 | 119.7 (3) |
C13—C12—H12 | 119.8 | C24—C23—H23 | 120.2 |
C11—C12—H12 | 119.8 | C22—C23—H23 | 120.2 |
C14—C13—C12 | 119.7 (2) | C25—C24—C23 | 120.1 (2) |
C14—C13—H13 | 120.2 | C25—C24—H24 | 119.9 |
C12—C13—H13 | 120.2 | C23—C24—H24 | 119.9 |
C13—C14—C15 | 120.7 (2) | C24—C25—C26 | 121.5 (3) |
C13—C14—H14 | 119.7 | C24—C25—H25 | 119.3 |
C15—C14—H14 | 119.7 | C26—C25—H25 | 119.3 |
C16—C15—C14 | 120.6 (3) | C25—C26—C21 | 117.6 (2) |
C16—C15—H15 | 119.7 | C25—C26—C27 | 119.2 (2) |
C14—C15—H15 | 119.7 | C21—C26—C27 | 123.3 (2) |
C15—C16—C11 | 118.3 (2) | O2—C27—C26 | 113.0 (2) |
C15—C16—C17 | 122.1 (2) | O2—C27—H27A | 109.0 |
C11—C16—C17 | 119.6 (2) | C26—C27—H27A | 109.0 |
O1—C17—C16 | 111.1 (2) | O2—C27—H27B | 109.0 |
O1—C17—H17A | 109.4 | C26—C27—H27B | 109.0 |
C16—C17—H17A | 109.4 | H27A—C27—H27B | 107.8 |
O1—C17—H17B | 109.4 | ||
C11—Se1—Se2—C21 | −74.30 (10) | Se1—Se2—C21—C22 | 92.33 (18) |
Se2—Se1—C11—C12 | 94.89 (18) | Se1—Se2—C21—C26 | −88.82 (18) |
Se2—Se1—C11—C16 | −85.27 (18) | C26—C21—C22—C23 | −0.7 (4) |
C16—C11—C12—C13 | 0.2 (4) | Se2—C21—C22—C23 | 178.10 (19) |
Se1—C11—C12—C13 | −179.92 (19) | C21—C22—C23—C24 | −0.7 (4) |
C11—C12—C13—C14 | 0.0 (4) | C22—C23—C24—C25 | 1.4 (4) |
C12—C13—C14—C15 | 0.3 (4) | C23—C24—C25—C26 | −0.7 (4) |
C13—C14—C15—C16 | −0.8 (4) | C24—C25—C26—C21 | −0.7 (4) |
C14—C15—C16—C11 | 1.0 (4) | C24—C25—C26—C27 | 179.4 (2) |
C14—C15—C16—C17 | −179.7 (2) | C22—C21—C26—C25 | 1.4 (3) |
C12—C11—C16—C15 | −0.7 (3) | Se2—C21—C26—C25 | −177.37 (17) |
Se1—C11—C16—C15 | 179.43 (17) | C22—C21—C26—C27 | −178.7 (2) |
C12—C11—C16—C17 | 179.9 (2) | Se2—C21—C26—C27 | 2.5 (3) |
Se1—C11—C16—C17 | 0.1 (3) | C25—C26—C27—O2 | 94.1 (3) |
C15—C16—C17—O1 | 6.4 (3) | C21—C26—C27—O2 | −85.7 (3) |
C11—C16—C17—O1 | −174.3 (2) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y−1, z+1. |
Experimental details
(I) | (II) | (IIIa) | |
Crystal data | |||
Chemical formula | C14H12Br2Se2 | C14H12Cl2Se2 | C14H14O2Se2 |
Mr | 497.98 | 409.06 | 372.17 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 296 | 200 | 200 |
a, b, c (Å) | 11.4093 (11), 11.3589 (11), 24.176 (2) | 7.9160 (2), 8.0215 (1), 23.4689 (4) | 8.4461 (2), 8.9003 (3), 9.7427 (3) |
α, β, γ (°) | 90, 101.861 (2), 90 | 98.388 (1), 95.287 (1), 90.610 (1) | 72.904 (1), 78.950 (1), 76.978 (1) |
V (Å3) | 3066.2 (5) | 1467.58 (5) | 675.81 (4) |
Z | 8 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 10.02 | 5.38 | 5.46 |
Crystal size (mm) | 0.13 × 0.11 × 0.04 | 0.21 × 0.20 × 0.06 | 0.24 × 0.16 × 0.10 |
Data collection | |||
Diffractometer | Bruker APEX CCD diffractometer | Bruker SMART CCD diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2008b) | Multi-scan (SADABS; Sheldrick, 2008b) | Multi-scan (SADABS; Sheldrick, 2008b) |
Tmin, Tmax | 0.346, 0.670 | 0.390, 0.724 | 0.336, 0.581 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12556, 2811, 1907 | 14837, 6651, 4403 | 6951, 3051, 2667 |
Rint | 0.048 | 0.056 | 0.029 |
(sin θ/λ)max (Å−1) | 0.603 | 0.648 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.082, 1.02 | 0.050, 0.100, 1.04 | 0.026, 0.071, 1.09 |
No. of reflections | 2811 | 6651 | 3051 |
No. of parameters | 163 | 325 | 171 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.58, −0.46 | 0.49, −0.51 | 0.60, −0.52 |
Computer programs: SMART (Bruker, 2001), SMART (Bruker, 1995), SAINT (Bruker, 2001), SAINT (Bruker, 1995), SHELXTL (Sheldrick, 2008a).
Se1—C11 | 1.935 (5) | Se2—C21 | 1.941 (5) |
Se1—Se2 | 2.3090 (9) | ||
C11—Se1—Se2 | 101.69 (15) | C21—Se2—Se1 | 103.12 (16) |
C11—Se1—Se2—C21 | 87.6 (2) |
Se1A—C11A | 1.937 (4) | Se1B—C11B | 1.935 (4) |
Se1A—Se2A | 2.3124 (8) | Se1B—Se2B | 2.3140 (8) |
Se2A—C21A | 1.944 (4) | Se2B—C21B | 1.928 (4) |
C11A—Se1A—Se2A | 103.20 (14) | C11B—Se1B—Se2B | 103.60 (14) |
C21A—Se2A—Se1A | 100.96 (14) | C21B—Se2B—Se1B | 102.10 (14) |
C11A—Se1A—Se2A—C21A | −90.15 (19) | C11B—Se1B—Se2B—C21B | −85.08 (19) |
Se1—C11 | 1.924 (2) | Se2—H17Bi | 3.0920 |
Se1—Se2 | 2.3441 (3) | O1—O2i | 2.747 (3) |
Se2—C21 | 1.929 (2) | O1—O2ii | 2.790 (3) |
Se2—Se2i | 3.7646 (5) | ||
C11—Se1—Se2 | 98.92 (7) | C21—Se2—Se2i | 174.82 (7) |
C21—Se2—Se1 | 99.06 (7) | ||
C11—Se1—Se2—C21 | −74.30 (10) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y−1, z+1. |
Contacts | (I) | (II) | (IIIa) | (IIIb) | (IV) |
Se1···X1 | 3.828 (1) | 3.537 (2)/3.471 (2) | none | none | 2.856 (3) |
Se2···X2 | 3.673 (1) | 3.681 (2)/3.679 (2) | none | 3.008 (3) | 2.863 (4) |
rW(Se) + rW(X) | 3.75 | 3.65 | 3.42 | 3.42 | 3.45 |
Angles | |||||
Se2—Se1···X1 | 167.97 (3) | 166.39 (4) / 173.35 (4) | - | - | 174.0 (1) |
Se1—Se2···X2 | 170.02 (3) | 162.51 (3) / 169.83 (3) | - | 166.1 (1) | 172.7 (1) |
Interplanar angles | |||||
Ph–C11/Se1/Se2 | 37.8 (2) | 14.3 (1)/21.7 (1) | 85.06 (6) | 77.1 (1) | 17.3 |
Ph–C21/Se2/Se1 | 19.7 (3) | 43.2(1 /34.1 (1) | 88.32 (6) | 11.1 (1) | 26.0 |
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Organic selenides and diselenides tend to form close contacts with centres such as halogens (Iwaoka et al., 2000, 2005; Iwaoka, Katsuda et al., 2002; Iwaoka, Komatsu et al., 2002; Nakanishi et al., 1998) and chalcogens (Bleiholder et al., 2006, 2007; Gleiter et al., 2003, 2005; Mundt et al., 2006; Schulte et al., 2003; Werz et al., 2002a,b, 2008; Lari et al., 2009).
In bis[2-(bromomethyl)phenyl] diselenide, (I), and bis[2-(chloromethyl)phenyl] diselenide, (II), the halogen centres are properly situated to form contacts with the diselenide unit. Such an arrangement of an oxygen centre and a diselenide unit has also been reported for the structure of 2,2'-(diselenodi-ophenylene)dimethanol, (IIIb) (Tripathi et al., 2005). Similarly, an almost linear arrangement of two dimethylamine units and a diselenide bridge was reported for bis{2-[(dimethylamino)methyl]phenyl} diselenide, (IV) (Kaur et al., 1996). Common to all the conformations with contacts between the donor atoms and the diselenide unit is a rather small torsion angle between the benzene plane and the Se—Se vector. In addition to the selenium contacts, the OH groups of the 2,2'-diselenodibenzyl alcohol (III) provide the opportunity [have the potential?] to form intermolecular hydrogen bonds; such hydrogen bonds were found in the new modification (IIIa).
The molecular structures of (I) and (II) (Figs. 1 and 2, Tables 1 and 2) have in common a central Se1—Se2 unit which interacts with peripheral donor centres, Br in in (I) or Cl in in (II). A new modification of (III), denoted (IIIa) (Fig. 3, Table 3), was obtained when (III) was crystallized from a light petroleum/dichloromethane mixture, whereas the known modification (IIIb) (P21/n, Z = 4; Tripathi et al., 2005) was crystallized from toluene.
For (IIIa) we found no significant interactions between selenium and oxygen. The intramolecular Se···O distances are 3.687 (2) and 4.586 (2) Å, considerably longer than the sum of the van der Waals radii of Se and O. Interesting features of the solid-state structure of (IIIa) are not only O—H···O hydrogen bonds with O···O distances of 2.747 (3) Å, but also a short intermolecular Se···Se contact and an intermolecular Se···H contact involving a benzylic H atom (Table 3). These interactions cause a pairing of molecules (Fig. 3), and these pairs are linked into chains by a second pair of hydrogen bonds [O···O 2.790 (3) Å].
Table 4 presents a comparison of the geometric parameters related to the Se···X contacts of the three structures plus the data for the previously published structures (IIIb) (Tripathi et al., 2005) and (IV) (Kaur et al., 1996). For (I) and (II) one notices rather short Se···halogen contacts and an almost linear arrangement of this interaction with the Se1—Se2 bond direction. In the case of (IIIb) only one of the oxygen centres forms a short contact with the Se1—Se2 unit, with an almost linear Se1—Se2···O2 array. The other oxygen is situated at a distance of 4.637 (3) Å, which is much further than the van der Waals distance of 3.42 Å (Bondi, 1964). In the case of (IV) one finds short Se···N contacts and an almost linear arrangement of the N···Se—Se···N centres again. We notice a close relationship between the angles between the benzene planes and the Se–Se units and the strength of the contacts. In cases where these angles are near 90°, there are no contacts; for angles around 40° the contacts are in the range of the van der Waals distances; whereas smaller angles in the range of 20° to 10° result in even shorter contacts. We ascribe this to the fact that only a small torsion angle allows the donor atoms to approach the diselenide unit in the direction opposite to the Se—Se bond. We assume an attractive Se···X interaction composed of dispersion forces and directed forces between the lone pairs of the donor atoms with the σ*-acceptor orbital of the Se—Se bond (Bleiholder et al., 2006, 2007). However, the Se—Se distances do not seem to be affected by the interaction. If there is an effect on the Se—Se bond length it is compensated for by other influences.
The torsion angles between Se—C bonds along the Se—Se axis (C11—Se1—Se2—C21) are close to 90° in all cases. This conformation of the diselenide units is preferred due to the repulsion of the 4p lone pairs at the Se centres.