Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010605150X/av3053sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010605150X/av3053Isup2.hkl |
CCDC reference: 638301
For related literature, see: Novak et al. (2006); Varga et al. (2001, 2005, 2006).
The title compound was obtained by the reaction between [{2-(Me2NCH2)C6H4}{2-(Me2NHCH2)C6H4}SnCl2]+[{2-(Me2NCH2)C6H4}SnC4]- and excess KBr in a CH2Cl2–H2O mixture (Ratio of solvents?). Crystals of (I) suitable for X-ray diffraction were obtained from a solution in a CH2Cl2–n-hexane mixture (Ratio of solvents?).
All H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93–0.97 Å [Please check added text], and with Uiso(H) = 1.5Ueq(C) for methyl H or 1.2Ueq(C) for aryl H atoms. The methyl groups were allowed to rotate but not to tip. Atom H3A bonded to N3 was calculated and fixed at the standard N—H distance of 0.87 (5) Å.
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2006).
[SnBr2(C9H12N)2][SnBr4(C9H12N)] | F(000) = 2120 |
Mr = 1120.44 | Dx = 2.133 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4671 reflections |
a = 9.5330 (5) Å | θ = 2.2–22.7° |
b = 36.635 (2) Å | µ = 8.33 mm−1 |
c = 10.0344 (6) Å | T = 297 K |
β = 95.479 (1)° | Block, colourless |
V = 3488.4 (3) Å3 | 0.24 × 0.21 × 0.12 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 6137 independent reflections |
Radiation source: fine-focus sealed tube | 5141 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.141, Tmax = 0.368 | k = −43→42 |
25246 measured reflections | l = −11→11 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P] where P = (Fo2 + 2Fc2)/3 |
6137 reflections | (Δ/σ)max = 0.001 |
353 parameters | Δρmax = 1.10 e Å−3 |
1 restraint | Δρmin = −0.98 e Å−3 |
[SnBr2(C9H12N)2][SnBr4(C9H12N)] | V = 3488.4 (3) Å3 |
Mr = 1120.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.5330 (5) Å | µ = 8.33 mm−1 |
b = 36.635 (2) Å | T = 297 K |
c = 10.0344 (6) Å | 0.24 × 0.21 × 0.12 mm |
β = 95.479 (1)° |
Bruker SMART CCD area-detector diffractometer | 6137 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5141 reflections with I > 2σ(I) |
Tmin = 0.141, Tmax = 0.368 | Rint = 0.048 |
25246 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 1 restraint |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P] where P = (Fo2 + 2Fc2)/3 |
6137 reflections | Δρmax = 1.10 e Å−3 |
353 parameters | Δρmin = −0.98 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.45399 (9) | 0.43640 (3) | 0.20347 (9) | 0.0497 (2) | |
Br2 | 0.72725 (11) | 0.49177 (3) | 0.06030 (9) | 0.0540 (3) | |
Br3 | 0.70387 (11) | 0.39449 (3) | −0.01387 (9) | 0.0581 (3) | |
Br4 | 0.74413 (9) | 0.47849 (2) | 0.42327 (8) | 0.0468 (2) | |
C1 | 0.7793 (9) | 0.3864 (2) | 0.3139 (8) | 0.0409 (19) | |
C2 | 0.9253 (10) | 0.3803 (3) | 0.3399 (10) | 0.058 (3) | |
C3 | 0.9685 (13) | 0.3463 (3) | 0.3881 (11) | 0.077 (3) | |
H3 | 1.0642 | 0.3411 | 0.4026 | 0.092* | |
C4 | 0.8705 (15) | 0.3202 (3) | 0.4150 (12) | 0.082 (4) | |
H4 | 0.9013 | 0.2977 | 0.4493 | 0.098* | |
C5 | 0.7335 (14) | 0.3266 (3) | 0.3927 (11) | 0.074 (3) | |
H5 | 0.6693 | 0.3086 | 0.4108 | 0.089* | |
C6 | 0.6856 (11) | 0.3598 (3) | 0.3427 (10) | 0.063 (3) | |
H6 | 0.5893 | 0.3643 | 0.3284 | 0.076* | |
C7 | 1.0245 (10) | 0.4133 (3) | 0.3300 (11) | 0.075 (3) | |
H7A | 1.0275 | 0.4273 | 0.4123 | 0.090* | |
H7B | 1.1191 | 0.4046 | 0.3205 | 0.090* | |
C8 | 1.0463 (11) | 0.4732 (3) | 0.2422 (13) | 0.082 (4) | |
H8A | 1.0119 | 0.4843 | 0.3194 | 0.124* | |
H8B | 1.0230 | 0.4883 | 0.1652 | 0.124* | |
H8C | 1.1468 | 0.4705 | 0.2567 | 0.124* | |
C9 | 1.0307 (11) | 0.4239 (4) | 0.0935 (11) | 0.079 (4) | |
H9A | 1.1316 | 0.4220 | 0.1043 | 0.119* | |
H9B | 1.0029 | 0.4410 | 0.0233 | 0.119* | |
H9C | 0.9905 | 0.4005 | 0.0709 | 0.119* | |
N1 | 0.9803 (7) | 0.43670 (19) | 0.2192 (7) | 0.0423 (16) | |
Sn1 | 0.72496 (5) | 0.434562 (14) | 0.20284 (5) | 0.03062 (15) | |
Br5 | 0.64191 (13) | 0.67775 (4) | 0.47850 (12) | 0.0798 (4) | |
Br6 | 0.86476 (12) | 0.73173 (3) | 0.25672 (14) | 0.0775 (4) | |
C10 | 0.5011 (8) | 0.6955 (2) | 0.1426 (10) | 0.045 (2) | |
C11 | 0.4985 (10) | 0.7084 (2) | 0.0144 (12) | 0.059 (3) | |
C12 | 0.3707 (11) | 0.7212 (3) | −0.0497 (13) | 0.073 (3) | |
H12 | 0.3685 | 0.7301 | −0.1367 | 0.088* | |
C13 | 0.2503 (12) | 0.7208 (3) | 0.0122 (16) | 0.084 (4) | |
H13 | 0.1656 | 0.7286 | −0.0322 | 0.101* | |
C14 | 0.2563 (11) | 0.7087 (3) | 0.1404 (15) | 0.079 (4) | |
H14 | 0.1749 | 0.7097 | 0.1845 | 0.095* | |
C15 | 0.3779 (10) | 0.6951 (2) | 0.2084 (12) | 0.062 (3) | |
H15 | 0.3780 | 0.6860 | 0.2949 | 0.074* | |
C16 | 0.6323 (10) | 0.7107 (3) | −0.0535 (11) | 0.059 (3) | |
H16A | 0.6106 | 0.7095 | −0.1498 | 0.071* | |
H16B | 0.6791 | 0.7337 | −0.0318 | 0.071* | |
C17 | 0.6689 (10) | 0.6456 (2) | −0.0668 (9) | 0.051 (2) | |
H17A | 0.6668 | 0.6469 | −0.1625 | 0.077* | |
H17B | 0.5750 | 0.6420 | −0.0422 | 0.077* | |
H17C | 0.7275 | 0.6256 | −0.0341 | 0.077* | |
C18 | 0.8708 (9) | 0.6860 (3) | −0.0465 (10) | 0.057 (2) | |
H18A | 0.8684 | 0.6866 | −0.1423 | 0.086* | |
H18B | 0.9307 | 0.6664 | −0.0123 | 0.086* | |
H18C | 0.9068 | 0.7087 | −0.0100 | 0.086* | |
C19 | 0.8353 (8) | 0.6317 (2) | 0.2496 (8) | 0.0387 (19) | |
C20 | 0.7922 (7) | 0.5944 (2) | 0.2438 (7) | 0.0317 (17) | |
C21 | 0.8938 (9) | 0.5675 (2) | 0.2645 (8) | 0.043 (2) | |
H21 | 0.8664 | 0.5432 | 0.2590 | 0.052* | |
C22 | 1.0337 (9) | 0.5757 (2) | 0.2929 (9) | 0.045 (2) | |
H22 | 1.0990 | 0.5570 | 0.3098 | 0.054* | |
C23 | 1.0770 (9) | 0.6106 (3) | 0.2963 (10) | 0.053 (2) | |
H23 | 1.1724 | 0.6161 | 0.3115 | 0.063* | |
C24 | 0.9785 (9) | 0.6383 (2) | 0.2772 (9) | 0.049 (2) | |
H24 | 1.0095 | 0.6624 | 0.2831 | 0.058* | |
C25 | 0.6412 (8) | 0.5834 (2) | 0.2101 (8) | 0.0383 (18) | |
H25A | 0.6311 | 0.5725 | 0.1216 | 0.046* | |
H25B | 0.5824 | 0.6051 | 0.2076 | 0.046* | |
C26 | 0.4527 (8) | 0.5405 (3) | 0.2609 (9) | 0.050 (2) | |
H26A | 0.3832 | 0.5594 | 0.2475 | 0.075* | |
H26B | 0.4250 | 0.5235 | 0.3262 | 0.075* | |
H26C | 0.4607 | 0.5280 | 0.1778 | 0.075* | |
C27 | 0.5888 (12) | 0.5725 (3) | 0.4452 (9) | 0.071 (3) | |
H27A | 0.5730 | 0.5535 | 0.5076 | 0.106* | |
H27B | 0.5148 | 0.5903 | 0.4451 | 0.106* | |
H27C | 0.6778 | 0.5840 | 0.4710 | 0.106* | |
H3A | 0.646 (6) | 0.5384 (13) | 0.327 (7) | 0.03 (2)* | |
N2 | 0.7261 (7) | 0.68006 (18) | −0.0076 (8) | 0.0477 (18) | |
N3 | 0.5902 (7) | 0.55679 (18) | 0.3088 (7) | 0.0373 (15) | |
Sn2 | 0.70216 (6) | 0.678224 (15) | 0.23036 (7) | 0.04434 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0368 (5) | 0.0539 (6) | 0.0579 (6) | 0.0008 (4) | 0.0027 (4) | −0.0052 (4) |
Br2 | 0.0672 (6) | 0.0466 (5) | 0.0469 (5) | −0.0040 (4) | −0.0011 (4) | 0.0065 (4) |
Br3 | 0.0668 (6) | 0.0589 (6) | 0.0479 (5) | 0.0018 (5) | 0.0018 (4) | −0.0090 (5) |
Br4 | 0.0543 (5) | 0.0491 (5) | 0.0367 (5) | 0.0063 (4) | 0.0033 (4) | −0.0026 (4) |
C1 | 0.043 (5) | 0.040 (5) | 0.039 (5) | 0.011 (4) | 0.001 (4) | 0.000 (4) |
C2 | 0.056 (6) | 0.057 (6) | 0.060 (6) | 0.017 (5) | 0.005 (5) | 0.017 (5) |
C3 | 0.078 (8) | 0.084 (8) | 0.067 (7) | 0.048 (7) | 0.002 (6) | 0.022 (6) |
C4 | 0.120 (11) | 0.050 (7) | 0.073 (8) | 0.021 (7) | −0.006 (7) | 0.020 (6) |
C5 | 0.088 (9) | 0.050 (7) | 0.082 (8) | −0.004 (6) | −0.004 (7) | 0.021 (6) |
C6 | 0.067 (7) | 0.045 (6) | 0.075 (7) | −0.002 (5) | −0.006 (5) | 0.024 (5) |
C7 | 0.044 (6) | 0.120 (10) | 0.061 (7) | 0.010 (6) | −0.003 (5) | 0.007 (7) |
C8 | 0.044 (6) | 0.087 (9) | 0.115 (10) | −0.003 (6) | 0.002 (6) | −0.026 (7) |
C9 | 0.051 (6) | 0.125 (11) | 0.066 (7) | 0.016 (6) | 0.020 (5) | −0.018 (7) |
N1 | 0.033 (4) | 0.050 (4) | 0.045 (4) | 0.007 (3) | 0.011 (3) | −0.004 (3) |
Sn1 | 0.0305 (3) | 0.0310 (3) | 0.0302 (3) | 0.0030 (2) | 0.0021 (2) | 0.0011 (2) |
Br5 | 0.0741 (8) | 0.0919 (9) | 0.0768 (8) | 0.0123 (6) | 0.0244 (6) | −0.0130 (7) |
Br6 | 0.0594 (6) | 0.0479 (6) | 0.1284 (11) | −0.0124 (5) | 0.0253 (6) | −0.0342 (6) |
C10 | 0.032 (4) | 0.026 (4) | 0.078 (7) | −0.004 (3) | 0.012 (4) | −0.006 (4) |
C11 | 0.046 (5) | 0.031 (5) | 0.101 (8) | 0.003 (4) | 0.010 (5) | 0.001 (5) |
C12 | 0.058 (7) | 0.055 (6) | 0.104 (9) | 0.004 (5) | −0.007 (6) | 0.006 (6) |
C13 | 0.044 (6) | 0.062 (7) | 0.145 (13) | 0.001 (5) | 0.001 (7) | 0.003 (8) |
C14 | 0.038 (6) | 0.062 (7) | 0.140 (12) | 0.005 (5) | 0.022 (7) | −0.025 (8) |
C15 | 0.046 (6) | 0.038 (5) | 0.104 (8) | −0.004 (4) | 0.021 (5) | −0.013 (5) |
C16 | 0.056 (6) | 0.046 (6) | 0.079 (7) | 0.008 (4) | 0.017 (5) | 0.020 (5) |
C17 | 0.061 (6) | 0.036 (5) | 0.058 (6) | −0.001 (4) | 0.015 (5) | 0.000 (4) |
C18 | 0.046 (5) | 0.055 (6) | 0.074 (7) | −0.004 (4) | 0.020 (5) | 0.009 (5) |
C19 | 0.032 (4) | 0.039 (5) | 0.048 (5) | 0.004 (3) | 0.017 (4) | −0.002 (4) |
C20 | 0.029 (4) | 0.039 (4) | 0.026 (4) | 0.000 (3) | 0.000 (3) | −0.001 (3) |
C21 | 0.046 (5) | 0.036 (5) | 0.048 (5) | −0.001 (4) | 0.003 (4) | 0.000 (4) |
C22 | 0.037 (5) | 0.044 (5) | 0.054 (5) | 0.008 (4) | 0.007 (4) | 0.001 (4) |
C23 | 0.028 (4) | 0.061 (6) | 0.070 (6) | −0.003 (4) | 0.005 (4) | −0.008 (5) |
C24 | 0.044 (5) | 0.036 (5) | 0.067 (6) | −0.005 (4) | 0.012 (4) | −0.008 (4) |
C25 | 0.045 (5) | 0.031 (4) | 0.038 (4) | 0.007 (4) | 0.000 (4) | 0.004 (3) |
C26 | 0.038 (5) | 0.053 (6) | 0.059 (6) | −0.013 (4) | 0.006 (4) | 0.006 (5) |
C27 | 0.077 (7) | 0.095 (8) | 0.042 (5) | −0.022 (6) | 0.015 (5) | −0.016 (5) |
N2 | 0.043 (4) | 0.031 (4) | 0.072 (5) | 0.001 (3) | 0.018 (4) | 0.004 (4) |
N3 | 0.033 (4) | 0.038 (4) | 0.041 (4) | −0.002 (3) | 0.003 (3) | 0.007 (3) |
Sn2 | 0.0339 (3) | 0.0310 (3) | 0.0699 (4) | 0.0004 (2) | 0.0141 (3) | −0.0094 (3) |
Br1—Sn1 | 2.5847 (10) | C13—C14 | 1.356 (18) |
Br2—Sn1 | 2.5386 (10) | C13—H13 | 0.9300 |
Br3—Sn1 | 2.6154 (10) | C14—C15 | 1.380 (15) |
Br4—Sn1 | 2.7274 (10) | C14—H14 | 0.9300 |
Br5—Sn2 | 2.6083 (14) | C15—H15 | 0.9300 |
Br6—Sn2 | 2.4975 (11) | C16—N2 | 1.481 (11) |
N1—Sn1 | 2.425 (6) | C16—H16A | 0.9700 |
N2—Sn2 | 2.421 (8) | C16—H16B | 0.9700 |
C1—Sn1 | 2.125 (8) | C17—N2 | 1.476 (11) |
C10—Sn2 | 2.128 (8) | C17—H17A | 0.9600 |
C19—Sn2 | 2.123 (8) | C17—H17B | 0.9600 |
C1—C6 | 1.369 (12) | C17—H17C | 0.9600 |
C1—C2 | 1.409 (12) | C18—N2 | 1.484 (10) |
C2—C3 | 1.384 (13) | C18—H18A | 0.9600 |
C2—C7 | 1.545 (15) | C18—H18B | 0.9600 |
C3—C4 | 1.382 (17) | C18—H18C | 0.9600 |
C3—H3 | 0.9300 | C19—C24 | 1.388 (11) |
C4—C5 | 1.325 (16) | C19—C20 | 1.425 (11) |
C4—H4 | 0.9300 | C20—C21 | 1.384 (11) |
C5—C6 | 1.378 (13) | C20—C25 | 1.502 (10) |
C5—H5 | 0.9300 | C21—C22 | 1.370 (11) |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
C7—N1 | 1.434 (12) | C22—C23 | 1.343 (12) |
C7—H7A | 0.9700 | C22—H22 | 0.9300 |
C7—H7B | 0.9700 | C23—C24 | 1.383 (12) |
C8—N1 | 1.486 (12) | C23—H23 | 0.9300 |
C8—H8A | 0.9600 | C24—H24 | 0.9300 |
C8—H8B | 0.9600 | C25—N3 | 1.503 (10) |
C8—H8C | 0.9600 | C25—H25A | 0.9700 |
C9—N1 | 1.468 (11) | C25—H25B | 0.9700 |
C9—H9A | 0.9600 | C26—N3 | 1.478 (10) |
C9—H9B | 0.9600 | C26—H26A | 0.9600 |
C9—H9C | 0.9600 | C26—H26B | 0.9600 |
C10—C11 | 1.368 (14) | C26—H26C | 0.9600 |
C10—C15 | 1.401 (12) | C27—N3 | 1.487 (11) |
C11—C12 | 1.403 (14) | C27—H27A | 0.9600 |
C11—C16 | 1.505 (13) | C27—H27B | 0.9600 |
C12—C13 | 1.357 (16) | C27—H27C | 0.9600 |
C12—H12 | 0.9300 | N3—H3A | 0.86 (2) |
C6—C1—C2 | 120.1 (8) | N2—C16—H16A | 109.8 |
C6—C1—Sn1 | 124.7 (6) | C11—C16—H16A | 109.8 |
C2—C1—Sn1 | 114.5 (6) | N2—C16—H16B | 109.8 |
C3—C2—C1 | 117.6 (10) | C11—C16—H16B | 109.8 |
C3—C2—C7 | 124.3 (10) | H16A—C16—H16B | 108.3 |
C1—C2—C7 | 117.7 (8) | N2—C17—H17A | 109.5 |
C4—C3—C2 | 120.5 (10) | N2—C17—H17B | 109.5 |
C4—C3—H3 | 119.8 | H17A—C17—H17B | 109.5 |
C2—C3—H3 | 119.8 | N2—C17—H17C | 109.5 |
C5—C4—C3 | 121.2 (10) | H17A—C17—H17C | 109.5 |
C5—C4—H4 | 119.4 | H17B—C17—H17C | 109.5 |
C3—C4—H4 | 119.4 | N2—C18—H18A | 109.5 |
C4—C5—C6 | 120.4 (11) | N2—C18—H18B | 109.5 |
C4—C5—H5 | 119.8 | H18A—C18—H18B | 109.5 |
C6—C5—H5 | 119.8 | N2—C18—H18C | 109.5 |
C1—C6—C5 | 120.3 (10) | H18A—C18—H18C | 109.5 |
C1—C6—H6 | 119.9 | H18B—C18—H18C | 109.5 |
C5—C6—H6 | 119.9 | C24—C19—C20 | 116.7 (7) |
N1—C7—C2 | 112.4 (8) | C24—C19—Sn2 | 116.5 (6) |
N1—C7—H7A | 109.1 | C20—C19—Sn2 | 126.7 (5) |
C2—C7—H7A | 109.1 | C21—C20—C19 | 118.7 (7) |
N1—C7—H7B | 109.1 | C21—C20—C25 | 119.0 (7) |
C2—C7—H7B | 109.1 | C19—C20—C25 | 122.2 (7) |
H7A—C7—H7B | 107.9 | C22—C21—C20 | 122.0 (8) |
N1—C8—H8A | 109.5 | C22—C21—H21 | 119.0 |
N1—C8—H8B | 109.5 | C20—C21—H21 | 119.0 |
H8A—C8—H8B | 109.5 | C23—C22—C21 | 120.3 (8) |
N1—C8—H8C | 109.5 | C23—C22—H22 | 119.9 |
H8A—C8—H8C | 109.5 | C21—C22—H22 | 119.9 |
H8B—C8—H8C | 109.5 | C22—C23—C24 | 119.5 (8) |
N1—C9—H9A | 109.5 | C22—C23—H23 | 120.3 |
N1—C9—H9B | 109.5 | C24—C23—H23 | 120.3 |
H9A—C9—H9B | 109.5 | C23—C24—C19 | 122.8 (8) |
N1—C9—H9C | 109.5 | C23—C24—H24 | 118.6 |
H9A—C9—H9C | 109.5 | C19—C24—H24 | 118.6 |
H9B—C9—H9C | 109.5 | C20—C25—N3 | 112.9 (6) |
C7—N1—C9 | 112.3 (8) | C20—C25—H25A | 109.0 |
C7—N1—C8 | 109.1 (8) | N3—C25—H25A | 109.0 |
C9—N1—C8 | 104.5 (8) | C20—C25—H25B | 109.0 |
C7—N1—Sn1 | 104.6 (5) | N3—C25—H25B | 109.0 |
C9—N1—Sn1 | 109.9 (6) | H25A—C25—H25B | 107.8 |
C8—N1—Sn1 | 116.6 (5) | N3—C26—H26A | 109.5 |
C1—Sn1—N1 | 78.4 (3) | N3—C26—H26B | 109.5 |
C1—Sn1—Br2 | 165.1 (2) | H26A—C26—H26B | 109.5 |
N1—Sn1—Br2 | 87.07 (17) | N3—C26—H26C | 109.5 |
C1—Sn1—Br1 | 102.3 (2) | H26A—C26—H26C | 109.5 |
N1—Sn1—Br1 | 174.79 (16) | H26B—C26—H26C | 109.5 |
Br2—Sn1—Br1 | 92.42 (4) | N3—C27—H27A | 109.5 |
C1—Sn1—Br3 | 88.0 (2) | N3—C27—H27B | 109.5 |
N1—Sn1—Br3 | 94.09 (16) | H27A—C27—H27B | 109.5 |
Br2—Sn1—Br3 | 89.94 (4) | N3—C27—H27C | 109.5 |
Br1—Sn1—Br3 | 91.10 (3) | H27A—C27—H27C | 109.5 |
C1—Sn1—Br4 | 94.1 (2) | H27B—C27—H27C | 109.5 |
N1—Sn1—Br4 | 86.39 (16) | C17—N2—C16 | 109.5 (7) |
Br2—Sn1—Br4 | 88.07 (3) | C17—N2—C18 | 109.6 (7) |
Br1—Sn1—Br4 | 88.41 (3) | C16—N2—C18 | 110.9 (7) |
Br3—Sn1—Br4 | 177.93 (4) | C17—N2—Sn2 | 107.9 (5) |
C11—C10—C15 | 120.4 (9) | C16—N2—Sn2 | 102.5 (5) |
C11—C10—Sn2 | 115.2 (6) | C18—N2—Sn2 | 116.1 (6) |
C15—C10—Sn2 | 124.4 (8) | C26—N3—C27 | 111.7 (7) |
C10—C11—C12 | 118.9 (10) | C26—N3—C25 | 112.4 (6) |
C10—C11—C16 | 120.3 (9) | C27—N3—C25 | 112.7 (7) |
C12—C11—C16 | 120.6 (10) | C26—N3—H3A | 105 (5) |
C13—C12—C11 | 121.5 (12) | C27—N3—H3A | 100 (5) |
C13—C12—H12 | 119.3 | C25—N3—H3A | 114 (5) |
C11—C12—H12 | 119.3 | C19—Sn2—C10 | 141.6 (3) |
C14—C13—C12 | 118.5 (11) | C19—Sn2—N2 | 90.0 (3) |
C14—C13—H13 | 120.8 | C10—Sn2—N2 | 75.5 (3) |
C12—C13—H13 | 120.8 | C19—Sn2—Br6 | 105.1 (2) |
C13—C14—C15 | 122.9 (11) | C10—Sn2—Br6 | 109.6 (2) |
C13—C14—H14 | 118.5 | N2—Sn2—Br6 | 88.09 (17) |
C15—C14—H14 | 118.5 | C19—Sn2—Br5 | 95.3 (2) |
C14—C15—C10 | 117.8 (11) | C10—Sn2—Br5 | 97.2 (3) |
C14—C15—H15 | 121.1 | N2—Sn2—Br5 | 172.63 (17) |
C10—C15—H15 | 121.1 | Br6—Sn2—Br5 | 95.46 (5) |
N2—C16—C11 | 109.2 (7) | ||
C6—C1—C2—C3 | 3.3 (14) | C11—C10—C15—C14 | −1.3 (13) |
Sn1—C1—C2—C3 | −167.7 (8) | Sn2—C10—C15—C14 | 177.2 (7) |
C6—C1—C2—C7 | −169.1 (9) | C10—C11—C16—N2 | 34.0 (12) |
Sn1—C1—C2—C7 | 20.0 (11) | C12—C11—C16—N2 | −149.5 (9) |
C1—C2—C3—C4 | −2.8 (16) | C24—C19—C20—C21 | −0.5 (11) |
C7—C2—C3—C4 | 168.9 (11) | Sn2—C19—C20—C21 | −177.1 (6) |
C2—C3—C4—C5 | 1.5 (19) | C24—C19—C20—C25 | −177.8 (7) |
C3—C4—C5—C6 | −0.4 (19) | Sn2—C19—C20—C25 | 5.5 (11) |
C2—C1—C6—C5 | −2.3 (15) | C19—C20—C21—C22 | 1.3 (12) |
Sn1—C1—C6—C5 | 167.6 (8) | C25—C20—C21—C22 | 178.7 (7) |
C4—C5—C6—C1 | 0.9 (18) | C20—C21—C22—C23 | −2.6 (13) |
C3—C2—C7—N1 | 148.2 (10) | C21—C22—C23—C24 | 3.0 (14) |
C1—C2—C7—N1 | −40.1 (13) | C22—C23—C24—C19 | −2.3 (14) |
C2—C7—N1—C9 | −84.2 (10) | C20—C19—C24—C23 | 1.0 (13) |
C2—C7—N1—C8 | 160.3 (8) | Sn2—C19—C24—C23 | 178.0 (7) |
C2—C7—N1—Sn1 | 34.9 (9) | C21—C20—C25—N3 | 53.1 (10) |
C6—C1—Sn1—N1 | −170.3 (8) | C19—C20—C25—N3 | −129.6 (7) |
C2—C1—Sn1—N1 | 0.2 (6) | C11—C16—N2—C17 | 72.1 (10) |
C6—C1—Sn1—Br2 | −157.9 (7) | C11—C16—N2—C18 | −166.8 (8) |
C2—C1—Sn1—Br2 | 12.5 (13) | C11—C16—N2—Sn2 | −42.2 (9) |
C6—C1—Sn1—Br1 | 15.0 (8) | C20—C25—N3—C26 | −168.4 (7) |
C2—C1—Sn1—Br1 | −174.5 (6) | C20—C25—N3—C27 | 64.3 (9) |
C6—C1—Sn1—Br3 | −75.7 (8) | C24—C19—Sn2—C10 | 156.8 (6) |
C2—C1—Sn1—Br3 | 94.8 (6) | C20—C19—Sn2—C10 | −26.6 (10) |
C6—C1—Sn1—Br4 | 104.3 (8) | C24—C19—Sn2—N2 | 90.5 (6) |
C2—C1—Sn1—Br4 | −85.3 (6) | C20—C19—Sn2—N2 | −92.8 (7) |
C7—N1—Sn1—C1 | −20.1 (6) | C24—C19—Sn2—Br6 | 2.5 (7) |
C9—N1—Sn1—C1 | 100.7 (7) | C20—C19—Sn2—Br6 | 179.1 (6) |
C8—N1—Sn1—C1 | −140.6 (7) | C24—C19—Sn2—Br5 | −94.6 (6) |
C7—N1—Sn1—Br2 | 163.1 (6) | C20—C19—Sn2—Br5 | 82.0 (7) |
C9—N1—Sn1—Br2 | −76.2 (7) | C11—C10—Sn2—C19 | −88.5 (8) |
C8—N1—Sn1—Br2 | 42.5 (7) | C15—C10—Sn2—C19 | 93.0 (8) |
C7—N1—Sn1—Br3 | −107.2 (6) | C11—C10—Sn2—N2 | −17.5 (6) |
C9—N1—Sn1—Br3 | 13.6 (7) | C15—C10—Sn2—N2 | 164.0 (8) |
C8—N1—Sn1—Br3 | 132.2 (7) | C11—C10—Sn2—Br6 | 65.1 (7) |
C7—N1—Sn1—Br4 | 74.8 (6) | C15—C10—Sn2—Br6 | −113.4 (7) |
C9—N1—Sn1—Br4 | −164.4 (7) | C11—C10—Sn2—Br5 | 163.6 (6) |
C8—N1—Sn1—Br4 | −45.7 (7) | C15—C10—Sn2—Br5 | −14.9 (7) |
C15—C10—C11—C12 | 0.1 (13) | C17—N2—Sn2—C10 | −82.6 (5) |
Sn2—C10—C11—C12 | −178.5 (7) | C16—N2—Sn2—C10 | 32.9 (5) |
C15—C10—C11—C16 | 176.6 (8) | C18—N2—Sn2—C10 | 154.0 (6) |
Sn2—C10—C11—C16 | −1.9 (11) | C17—N2—Sn2—Br6 | 166.6 (5) |
C10—C11—C12—C13 | −0.5 (16) | C16—N2—Sn2—Br6 | −77.9 (5) |
C16—C11—C12—C13 | −177.0 (10) | C18—N2—Sn2—Br6 | 43.2 (5) |
C11—C12—C13—C14 | 2.0 (18) | C17—N2—Sn2—Br5 | −74.5 (14) |
C12—C13—C14—C15 | −3.3 (18) | C16—N2—Sn2—Br5 | 41.0 (16) |
C13—C14—C15—C10 | 2.9 (16) | C18—N2—Sn2—Br5 | 162.1 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···Br4 | 0.86 (5) | 2.54 (5) | 3.373 (7) | 161 (5) |
C21—H21···Br2 | 0.93 | 2.96 | 3.714 (7) | 139 |
C26—H26C···Br2i | 0.96 | 2.94 | 3.698 (9) | 137 |
C26—H26A···Br3i | 0.96 | 2.94 | 3.652 (10) | 132 |
C17—H17B···Br3i | 0.96 | 3.07 | 3.999 (10) | 162 |
C3—H3···Br5ii | 0.93 | 3.02 | 3.926 (12) | 166 |
C26—H26B···Br4iii | 0.96 | 3.11 | 3.897 (9) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [SnBr2(C9H12N)2][SnBr4(C9H12N)] |
Mr | 1120.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 297 |
a, b, c (Å) | 9.5330 (5), 36.635 (2), 10.0344 (6) |
β (°) | 95.479 (1) |
V (Å3) | 3488.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 8.33 |
Crystal size (mm) | 0.24 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.141, 0.368 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25246, 6137, 5141 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.122, 1.11 |
No. of reflections | 6137 |
No. of parameters | 353 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
w = 1/[σ2(Fo2) + (0.0501P)2 + 13.0613P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.10, −0.98 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT-Plus (Bruker, 2000), SHELXTL (Bruker, 2001), SHELXTL, ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2006).
Br1—Sn1 | 2.5847 (10) | N1—Sn1 | 2.425 (6) |
Br2—Sn1 | 2.5386 (10) | N2—Sn2 | 2.421 (8) |
Br3—Sn1 | 2.6154 (10) | C1—Sn1 | 2.125 (8) |
Br4—Sn1 | 2.7274 (10) | C10—Sn2 | 2.128 (8) |
Br5—Sn2 | 2.6083 (14) | C19—Sn2 | 2.123 (8) |
Br6—Sn2 | 2.4975 (11) | ||
C1—Sn1—N1 | 78.4 (3) | Br1—Sn1—Br4 | 88.41 (3) |
C1—Sn1—Br2 | 165.1 (2) | Br3—Sn1—Br4 | 177.93 (4) |
N1—Sn1—Br2 | 87.07 (17) | C19—Sn2—C10 | 141.6 (3) |
C1—Sn1—Br1 | 102.3 (2) | C19—Sn2—N2 | 90.0 (3) |
N1—Sn1—Br1 | 174.79 (16) | C10—Sn2—N2 | 75.5 (3) |
Br2—Sn1—Br1 | 92.42 (4) | C19—Sn2—Br6 | 105.1 (2) |
C1—Sn1—Br3 | 88.0 (2) | C10—Sn2—Br6 | 109.6 (2) |
N1—Sn1—Br3 | 94.09 (16) | N2—Sn2—Br6 | 88.09 (17) |
Br2—Sn1—Br3 | 89.94 (4) | C19—Sn2—Br5 | 95.3 (2) |
Br1—Sn1—Br3 | 91.10 (3) | C10—Sn2—Br5 | 97.2 (3) |
C1—Sn1—Br4 | 94.1 (2) | N2—Sn2—Br5 | 172.63 (17) |
N1—Sn1—Br4 | 86.39 (16) | Br6—Sn2—Br5 | 95.46 (5) |
Br2—Sn1—Br4 | 88.07 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···Br4 | 0.86 (5) | 2.54 (5) | 3.373 (7) | 161 (5) |
C21—H21···Br2 | 0.93 | 2.96 | 3.714 (7) | 139 |
C26—H26C···Br2i | 0.96 | 2.94 | 3.698 (9) | 137 |
C26—H26A···Br3i | 0.96 | 2.94 | 3.652 (10) | 132 |
C17—H17B···Br3i | 0.96 | 3.07 | 3.999 (10) | 162 |
C3—H3···Br5ii | 0.93 | 3.02 | 3.926 (12) | 166 |
C26—H26B···Br4iii | 0.96 | 3.11 | 3.897 (9) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+1. |
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During our work on organotin(IV) halides containing the [2-(Me2NCH2)C6H4] group (Varga et al., 2001, 2005, 2006), we isolated the title compound, (I), in which two ionic organotin(IV) fragments are present (Fig. 1). The structure is similar to that of the chloride derivative (Novak et al., 2006), but for the latter no intra- or intermolecular interactions were discussed.
The cationic fragment of compound (I) contains an Sn atom with a trigonal–bipyramidal coordination geometry, due to the strong intramolecular N→Sn interaction established by the N atom of the pendant arm from one organic ligand [Sn2—N2 = 2.421 (8) Å], while the other pendant arm is protonated at the N atom and is twisted away from the Sn centre. The anion has a hexacoordinated Sn, atom with the C atom of the ligand and the N atom from the intramolecularly coordinated NMe2 group [Sn1—N1 = 2.425 (6) Å] in cis positions.
Both the (C,N)CSnBr2 and (C,N)SnBr4 cores are distorted from ideal geometry as a consequence of the small `bite' of the pendant arm ligand [C10—Sn2—N2 = 75.5 (3)° and C1—Sn1—N1 = 78.4 (3)°]. The deviation of the metal atom (Sn2) from the equatorial plane (C10/C19/Br6) is 0.23 Å towards atom Br5 in the case of cation, while in the anion, atom C1 is 0.55 Å out of the best plane determined by Sn1/Br3/Br2/Br4, towards the pendant arm.
The intramolecular N→Sn interaction induces planar chirality at the metal centre (Varga et al., 2005, 2006) and the title compound crystallizes as a racemate, i.e. a mixture of SN2RN1 and RN2SN1 isomers.
The anion and cation of (I) are linked together by a hydrogen contact between one Br atom from the SN1-[{2-(Me2NCH2)C6H4}SnBr4]- anion and the H atom from the protonated pendant arm of the RN2-[{2-(Me2NCH2)C6H4}{2-(Me2NHCH2)C6H4}SnBr2]+ cation [Br4···H3Ai = 2.54 (5) Å; symmetry code: (i) 1 - x, 1 - y, -z]. Also, another hydrogen-bond type of interaction is formed between the RN2SN1 and SN2RN1 units [Br4···H26A = 3.116 Å], leading to a dimeric fragment (Fig. 2). This fragment is repeated in a two-dimensional supramolecular arrangement through the weak Br···H contacts [range 2.94–3.11 Å] (Fig. 3).
By contrast, a different supramolecular arrangement based on Cl···H contacts is observed for the chloride analogue (Novak et al., 2006). On the basis of the CIF file kindly provided by the Cambridge Crystallographic Data Centre, we found that in this case the anion and cation are connected through two Cl···H interactions (Cl1···H17B = 2.81 and Cl3···H17C = 2.82 Å), while three other interactions (Cl1···H12' = 2.78, Cl1···H16B = 2.98 and Cl4···H1' = 2.39 Å; symmetry code: (') -x, -y, 1 - z] lead to the formation of a dimeric structure. An interaction between the dimeric units (Cl2···H18C = 2.89 Å) connects them into a polymeric chain.