Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037827/br6222sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037827/br6222Isup2.hkl |
CCDC reference: 293828
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.009 Å
- R factor = 0.048
- wR factor = 0.124
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.14
Author Response: Both maximum and minimum residual densities are in close vicinity (<1A) of heavy atoms (Br2 and Sn1) and are probably resulting from defects in the crystal, which can not be properly included into the model. The poor quality of the crystal was witnessed by streaks of diffuse scattering observable on the area detector together with quick decrease of refl. intensity at high theta angles. To the lower precision of integrated intensities also contributed overall high background due to fluorescence of Br atoms and rather tricky absorption correction from irregular shape of the ''crystal''. |
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Author Response: Low precision of refined parameters for light atoms was caused by defects in the crystal (see above). |
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
[SnBr2(C9H12N)2] | F(000) = 1064 |
Mr = 546.90 | Dx = 1.851 Mg m−3 |
Monoclinic, P21/n | Melting point: 518 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8370 (2) Å | Cell parameters from 23900 reflections |
b = 13.3470 (3) Å | θ = 1–27.5° |
c = 15.0230 (3) Å | µ = 5.38 mm−1 |
β = 95.8090 (13)° | T = 150 K |
V = 1962.31 (7) Å3 | Prism, colourless |
Z = 4 | 0.25 × 0.2 × 0.12 mm |
Nonius KappaCCD area-detector diffractometer | 4507 independent reflections |
Radiation source: fine-focus sealed tube | 3812 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
φ and ω scans to fill the Ewald sphere | h = −12→12 |
Absorption correction: integration (Gaussian; Coppens, 1970) | k = −17→17 |
Tmin = 0.288, Tmax = 0.659 | l = −19→19 |
29364 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0457P)2 + 11.5726P] where P = (Fo2 + 2Fc2)/3 |
4507 reflections | (Δ/σ)max < 0.001 |
212 parameters | Δρmax = 3.02 e Å−3 |
0 restraints | Δρmin = −1.41 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.51856 (4) | 0.15498 (3) | 0.75437 (3) | 0.02805 (12) | |
Br1 | 0.55258 (7) | 0.34712 (5) | 0.73016 (5) | 0.04504 (19) | |
Br2 | 0.39056 (7) | 0.19196 (6) | 0.89550 (5) | 0.0516 (2) | |
N1 | 0.6746 (5) | 0.1391 (4) | 0.6269 (3) | 0.0342 (11) | |
N2 | 0.4426 (5) | −0.0282 (4) | 0.7813 (3) | 0.0353 (11) | |
C11 | 0.7168 (6) | 0.1252 (4) | 0.8194 (4) | 0.0303 (11) | |
C12 | 0.8278 (6) | 0.1429 (4) | 0.7693 (4) | 0.0318 (12) | |
C13 | 0.9615 (6) | 0.1329 (5) | 0.8096 (5) | 0.0399 (14) | |
H13 | 1.0347 | 0.1433 | 0.7761 | 0.048* | |
C14 | 0.9852 (7) | 0.1076 (5) | 0.8991 (5) | 0.0458 (16) | |
H14 | 1.0745 | 0.1029 | 0.9258 | 0.055* | |
C15 | 0.8787 (7) | 0.0895 (5) | 0.9488 (4) | 0.0411 (14) | |
H15 | 0.8954 | 0.0717 | 1.0087 | 0.049* | |
C16 | 0.7432 (6) | 0.0981 (5) | 0.9084 (4) | 0.0378 (13) | |
H16 | 0.6708 | 0.0853 | 0.9421 | 0.045* | |
C17 | 0.8032 (6) | 0.1805 (5) | 0.6735 (4) | 0.0378 (13) | |
H17A | 0.7981 | 0.2531 | 0.6736 | 0.045* | |
H17B | 0.8795 | 0.1613 | 0.6410 | 0.045* | |
C18 | 0.7001 (8) | 0.0353 (6) | 0.6010 (5) | 0.0503 (17) | |
H18A | 0.6156 | 0.0046 | 0.5778 | 0.076* | |
H18B | 0.7389 | −0.0015 | 0.6524 | 0.076* | |
H18C | 0.7626 | 0.0348 | 0.5559 | 0.076* | |
C19 | 0.6349 (8) | 0.1974 (7) | 0.5460 (4) | 0.0534 (19) | |
H19A | 0.6973 | 0.1840 | 0.5023 | 0.080* | |
H19B | 0.6373 | 0.2675 | 0.5604 | 0.080* | |
H19C | 0.5440 | 0.1791 | 0.5222 | 0.080* | |
C21 | 0.3429 (5) | 0.1310 (4) | 0.6636 (4) | 0.0307 (12) | |
C22 | 0.2597 (6) | 0.0495 (4) | 0.6791 (4) | 0.0330 (12) | |
C23 | 0.1404 (6) | 0.0344 (5) | 0.6218 (4) | 0.0399 (14) | |
H23 | 0.0845 | −0.0202 | 0.6308 | 0.048* | |
C24 | 0.1049 (6) | 0.0998 (5) | 0.5519 (4) | 0.0397 (14) | |
H24 | 0.0242 | 0.0896 | 0.5152 | 0.048* | |
C25 | 0.1863 (6) | 0.1789 (5) | 0.5362 (5) | 0.0411 (14) | |
H25 | 0.1630 | 0.2215 | 0.4881 | 0.049* | |
C26 | 0.3057 (6) | 0.1954 (5) | 0.5934 (4) | 0.0383 (14) | |
H26 | 0.3606 | 0.2503 | 0.5839 | 0.046* | |
C27 | 0.2926 (6) | −0.0180 (5) | 0.7599 (4) | 0.0410 (14) | |
H27A | 0.2530 | 0.0100 | 0.8110 | 0.049* | |
H27B | 0.2526 | −0.0836 | 0.7476 | 0.049* | |
C28 | 0.4924 (8) | −0.0999 (5) | 0.7171 (5) | 0.0514 (17) | |
H28A | 0.5895 | −0.1077 | 0.7295 | 0.077* | |
H28B | 0.4715 | −0.0751 | 0.6573 | 0.077* | |
H28C | 0.4486 | −0.1636 | 0.7228 | 0.077* | |
C29 | 0.4733 (8) | −0.0693 (6) | 0.8715 (5) | 0.0528 (18) | |
H29A | 0.4250 | −0.1313 | 0.8762 | 0.079* | |
H29B | 0.4453 | −0.0225 | 0.9146 | 0.079* | |
H29C | 0.5698 | −0.0812 | 0.8828 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02222 (19) | 0.0304 (2) | 0.0322 (2) | −0.00079 (14) | 0.00557 (14) | −0.00554 (15) |
Br1 | 0.0354 (3) | 0.0264 (3) | 0.0721 (5) | 0.0022 (2) | −0.0008 (3) | −0.0050 (3) |
Br2 | 0.0362 (3) | 0.0733 (5) | 0.0480 (4) | −0.0042 (3) | 0.0180 (3) | −0.0266 (4) |
N1 | 0.027 (2) | 0.043 (3) | 0.033 (3) | 0.000 (2) | 0.012 (2) | 0.001 (2) |
N2 | 0.036 (3) | 0.032 (3) | 0.038 (3) | −0.004 (2) | 0.005 (2) | 0.007 (2) |
C11 | 0.029 (3) | 0.028 (3) | 0.034 (3) | 0.003 (2) | 0.001 (2) | −0.003 (2) |
C12 | 0.026 (3) | 0.027 (3) | 0.043 (3) | 0.004 (2) | 0.006 (2) | −0.004 (2) |
C13 | 0.031 (3) | 0.033 (3) | 0.056 (4) | 0.005 (2) | 0.004 (3) | −0.004 (3) |
C14 | 0.035 (3) | 0.042 (4) | 0.057 (4) | 0.009 (3) | −0.011 (3) | −0.009 (3) |
C15 | 0.045 (3) | 0.039 (3) | 0.037 (3) | 0.008 (3) | −0.005 (3) | −0.005 (3) |
C16 | 0.040 (3) | 0.036 (3) | 0.038 (3) | 0.005 (3) | 0.007 (3) | −0.002 (3) |
C17 | 0.025 (3) | 0.042 (3) | 0.047 (4) | −0.002 (2) | 0.008 (3) | 0.002 (3) |
C18 | 0.055 (4) | 0.052 (4) | 0.046 (4) | 0.003 (3) | 0.015 (3) | −0.014 (3) |
C19 | 0.049 (4) | 0.078 (5) | 0.036 (3) | −0.010 (4) | 0.015 (3) | 0.017 (3) |
C21 | 0.024 (2) | 0.031 (3) | 0.038 (3) | −0.001 (2) | 0.004 (2) | −0.007 (2) |
C22 | 0.031 (3) | 0.035 (3) | 0.035 (3) | −0.004 (2) | 0.011 (2) | −0.003 (2) |
C23 | 0.037 (3) | 0.046 (4) | 0.039 (3) | −0.005 (3) | 0.011 (3) | −0.002 (3) |
C24 | 0.027 (3) | 0.056 (4) | 0.037 (3) | 0.001 (3) | 0.005 (2) | −0.006 (3) |
C25 | 0.030 (3) | 0.040 (3) | 0.051 (4) | 0.008 (3) | −0.003 (3) | 0.005 (3) |
C26 | 0.030 (3) | 0.032 (3) | 0.052 (4) | −0.001 (2) | 0.001 (3) | 0.003 (3) |
C27 | 0.035 (3) | 0.044 (4) | 0.045 (3) | −0.012 (3) | 0.009 (3) | 0.006 (3) |
C28 | 0.059 (4) | 0.034 (3) | 0.062 (4) | 0.010 (3) | 0.011 (4) | 0.000 (3) |
C29 | 0.060 (4) | 0.052 (4) | 0.045 (4) | −0.014 (3) | −0.001 (3) | 0.018 (3) |
Sn1—C21 | 2.114 (5) | C18—H18A | 0.9600 |
Sn1—C11 | 2.128 (5) | C18—H18B | 0.9600 |
Sn1—N1 | 2.581 (5) | C18—H18C | 0.9600 |
Sn1—N2 | 2.600 (5) | C19—H19A | 0.9600 |
Sn1—Br1 | 2.6164 (7) | C19—H19B | 0.9600 |
Sn1—Br2 | 2.6201 (7) | C19—H19C | 0.9600 |
N1—C19 | 1.463 (8) | C21—C26 | 1.382 (9) |
N1—C18 | 1.468 (9) | C21—C22 | 1.394 (8) |
N1—C17 | 1.488 (8) | C22—C23 | 1.398 (8) |
N2—C29 | 1.466 (8) | C22—C27 | 1.520 (9) |
N2—C28 | 1.477 (9) | C23—C24 | 1.384 (9) |
N2—C27 | 1.484 (8) | C23—H23 | 0.9300 |
C11—C16 | 1.385 (8) | C24—C25 | 1.360 (9) |
C11—C12 | 1.408 (8) | C24—H24 | 0.9300 |
C12—C13 | 1.397 (8) | C25—C26 | 1.400 (8) |
C12—C17 | 1.521 (9) | C25—H25 | 0.9300 |
C13—C14 | 1.383 (10) | C26—H26 | 0.9300 |
C13—H13 | 0.9300 | C27—H27A | 0.9700 |
C14—C15 | 1.368 (10) | C27—H27B | 0.9700 |
C14—H14 | 0.9300 | C28—H28A | 0.9600 |
C15—C16 | 1.412 (9) | C28—H28B | 0.9600 |
C15—H15 | 0.9300 | C28—H28C | 0.9600 |
C16—H16 | 0.9300 | C29—H29A | 0.9600 |
C17—H17A | 0.9700 | C29—H29B | 0.9600 |
C17—H17B | 0.9700 | C29—H29C | 0.9600 |
C21—Sn1—C11 | 156.7 (2) | H17A—C17—H17B | 108.0 |
C21—Sn1—N1 | 91.02 (19) | N1—C18—H18A | 109.5 |
C11—Sn1—N1 | 74.87 (19) | N1—C18—H18B | 109.5 |
C21—Sn1—N2 | 74.25 (19) | H18A—C18—H18B | 109.5 |
C11—Sn1—N2 | 91.02 (19) | N1—C18—H18C | 109.5 |
N1—Sn1—N2 | 103.88 (16) | H18A—C18—H18C | 109.5 |
C21—Sn1—Br1 | 99.60 (16) | H18B—C18—H18C | 109.5 |
C11—Sn1—Br1 | 97.03 (16) | N1—C19—H19A | 109.5 |
N1—Sn1—Br1 | 83.30 (12) | N1—C19—H19B | 109.5 |
N2—Sn1—Br1 | 170.43 (11) | H19A—C19—H19B | 109.5 |
C21—Sn1—Br2 | 97.02 (15) | N1—C19—H19C | 109.5 |
C11—Sn1—Br2 | 99.02 (16) | H19A—C19—H19C | 109.5 |
N1—Sn1—Br2 | 170.52 (12) | H19B—C19—H19C | 109.5 |
N2—Sn1—Br2 | 83.23 (12) | C26—C21—C22 | 119.9 (5) |
Br1—Sn1—Br2 | 90.37 (3) | C26—C21—Sn1 | 122.3 (4) |
C19—N1—C18 | 108.7 (6) | C22—C21—Sn1 | 117.8 (4) |
C19—N1—C17 | 109.6 (5) | C21—C22—C23 | 118.7 (6) |
C18—N1—C17 | 108.4 (5) | C21—C22—C27 | 120.9 (5) |
C19—N1—Sn1 | 116.3 (4) | C23—C22—C27 | 120.2 (5) |
C18—N1—Sn1 | 113.9 (4) | C24—C23—C22 | 120.5 (6) |
C17—N1—Sn1 | 99.3 (3) | C24—C23—H23 | 119.8 |
C29—N2—C28 | 108.0 (6) | C22—C23—H23 | 119.8 |
C29—N2—C27 | 110.0 (5) | C25—C24—C23 | 120.9 (6) |
C28—N2—C27 | 107.8 (5) | C25—C24—H24 | 119.5 |
C29—N2—Sn1 | 117.4 (4) | C23—C24—H24 | 119.5 |
C28—N2—Sn1 | 112.9 (4) | C24—C25—C26 | 119.2 (6) |
C27—N2—Sn1 | 100.1 (3) | C24—C25—H25 | 120.4 |
C16—C11—C12 | 118.7 (5) | C26—C25—H25 | 120.4 |
C16—C11—Sn1 | 124.4 (4) | C21—C26—C25 | 120.8 (6) |
C12—C11—Sn1 | 116.6 (4) | C21—C26—H26 | 119.6 |
C13—C12—C11 | 119.9 (6) | C25—C26—H26 | 119.6 |
C13—C12—C17 | 119.7 (5) | N2—C27—C22 | 110.7 (5) |
C11—C12—C17 | 120.2 (5) | N2—C27—H27A | 109.5 |
C14—C13—C12 | 120.3 (6) | C22—C27—H27A | 109.5 |
C14—C13—H13 | 119.9 | N2—C27—H27B | 109.5 |
C12—C13—H13 | 119.9 | C22—C27—H27B | 109.5 |
C15—C14—C13 | 120.6 (6) | H27A—C27—H27B | 108.1 |
C15—C14—H14 | 119.7 | N2—C28—H28A | 109.5 |
C13—C14—H14 | 119.7 | N2—C28—H28B | 109.5 |
C14—C15—C16 | 119.6 (6) | H28A—C28—H28B | 109.5 |
C14—C15—H15 | 120.2 | N2—C28—H28C | 109.5 |
C16—C15—H15 | 120.2 | H28A—C28—H28C | 109.5 |
C11—C16—C15 | 120.8 (6) | H28B—C28—H28C | 109.5 |
C11—C16—H16 | 119.6 | N2—C29—H29A | 109.5 |
C15—C16—H16 | 119.6 | N2—C29—H29B | 109.5 |
N1—C17—C12 | 111.6 (5) | H29A—C29—H29B | 109.5 |
N1—C17—H17A | 109.3 | N2—C29—H29C | 109.5 |
C12—C17—H17A | 109.3 | H29A—C29—H29C | 109.5 |
N1—C17—H17B | 109.3 | H29B—C29—H29C | 109.5 |
C12—C17—H17B | 109.3 |
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