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The Sn atom in the title complex, [Sn(CH3)3(C6H3BrNO2)(H2O)], is five-coordinate with a distorted trigonal-bipyramidal geometry. The O atom of the carboxylate group occupies one of the axial sites and the O atom of the water molecule occupies the other. Water H atoms are involved in an intermolecular hydrogen-bonded network with the uncoordinated carboxylate O atom and the pyridine N atom.
Supporting information
CCDC reference: 646696
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.024
- wR factor = 0.062
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.84
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.843
Tmax scaled 0.363 Tmin scaled 0.220
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Aqua(5-bromidonicotinato)trimethyltin(IV)
top
Crystal data top
[Sn(CH3)3(C6H3BrNO2)(H2O)] | F(000) = 1472 |
Mr = 382.81 | Dx = 1.879 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5271 reflections |
a = 10.9478 (18) Å | θ = 2.7–28.3° |
b = 12.688 (2) Å | µ = 4.83 mm−1 |
c = 19.479 (3) Å | T = 298 K |
V = 2705.7 (8) Å3 | Block, colourless |
Z = 8 | 0.38 × 0.27 × 0.21 mm |
Data collection top
Siemens SMART CCD area detector diffractometer | 2376 independent reflections |
Radiation source: fine-focus sealed tube | 1902 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.261, Tmax = 0.430 | k = −15→11 |
13116 measured reflections | l = −22→23 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0224P)2 + 2.0093P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2376 reflections | Δρmax = 0.59 e Å−3 |
137 parameters | Δρmin = −0.70 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0068 (2) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.08052 (2) | 0.79410 (2) | 0.443714 (12) | 0.03689 (12) | |
Br1 | 0.51645 (4) | 0.42788 (4) | 0.19060 (3) | 0.07111 (19) | |
N1 | 0.2127 (3) | 0.6088 (3) | 0.15353 (15) | 0.0533 (9) | |
O1 | 0.1338 (2) | 0.7342 (2) | 0.34276 (12) | 0.0533 (7) | |
O2 | 0.3138 (3) | 0.6883 (3) | 0.38511 (15) | 0.0800 (11) | |
O3 | 0.0244 (3) | 0.8661 (2) | 0.55392 (12) | 0.0578 (8) | |
H1 | −0.0370 | 0.8423 | 0.5757 | 0.087* | |
H3 | 0.0843 | 0.8651 | 0.5817 | 0.087* | |
C1 | 0.2378 (4) | 0.6909 (3) | 0.3385 (2) | 0.0508 (11) | |
C2 | 0.1938 (4) | 0.6546 (3) | 0.21436 (19) | 0.0478 (10) | |
H2 | 0.1276 | 0.7000 | 0.2187 | 0.057* | |
C3 | 0.2664 (3) | 0.6386 (3) | 0.27056 (18) | 0.0418 (9) | |
C4 | 0.3659 (4) | 0.5709 (3) | 0.26489 (19) | 0.0455 (10) | |
H4 | 0.4175 | 0.5585 | 0.3019 | 0.055* | |
C5 | 0.3850 (3) | 0.5232 (3) | 0.20255 (19) | 0.0435 (9) | |
C6 | 0.3082 (4) | 0.5437 (3) | 0.1486 (2) | 0.0532 (11) | |
H6 | 0.3233 | 0.5108 | 0.1068 | 0.064* | |
C7 | −0.0904 (4) | 0.8445 (4) | 0.4056 (2) | 0.0624 (12) | |
H7A | −0.1401 | 0.8691 | 0.4429 | 0.094* | |
H7B | −0.1305 | 0.7867 | 0.3832 | 0.094* | |
H7C | −0.0784 | 0.9007 | 0.3733 | 0.094* | |
C8 | 0.2204 (4) | 0.9066 (4) | 0.4515 (2) | 0.0656 (13) | |
H8A | 0.2837 | 0.8802 | 0.4810 | 0.098* | |
H8B | 0.1879 | 0.9706 | 0.4704 | 0.098* | |
H8C | 0.2536 | 0.9203 | 0.4068 | 0.098* | |
C9 | 0.0833 (4) | 0.6446 (3) | 0.4915 (3) | 0.0675 (13) | |
H9A | 0.1594 | 0.6355 | 0.5153 | 0.101* | |
H9B | 0.0748 | 0.5907 | 0.4573 | 0.101* | |
H9C | 0.0171 | 0.6398 | 0.5236 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.03133 (17) | 0.04129 (18) | 0.03805 (17) | 0.00294 (12) | 0.00110 (11) | −0.00087 (11) |
Br1 | 0.0585 (3) | 0.0782 (4) | 0.0766 (3) | 0.0206 (3) | 0.0111 (3) | −0.0196 (3) |
N1 | 0.056 (2) | 0.065 (2) | 0.0385 (19) | 0.0045 (19) | −0.0035 (16) | −0.0093 (16) |
O1 | 0.0421 (16) | 0.077 (2) | 0.0403 (15) | 0.0225 (15) | −0.0007 (13) | −0.0146 (13) |
O2 | 0.0576 (19) | 0.132 (3) | 0.0504 (18) | 0.039 (2) | −0.0187 (16) | −0.0360 (18) |
O3 | 0.0426 (16) | 0.091 (2) | 0.0400 (15) | −0.0130 (16) | 0.0070 (13) | −0.0098 (14) |
C1 | 0.042 (2) | 0.069 (3) | 0.042 (2) | 0.006 (2) | 0.002 (2) | −0.013 (2) |
C2 | 0.041 (2) | 0.057 (3) | 0.046 (2) | 0.005 (2) | 0.0000 (19) | −0.0089 (19) |
C3 | 0.035 (2) | 0.052 (2) | 0.039 (2) | 0.0012 (19) | 0.0038 (17) | −0.0058 (17) |
C4 | 0.037 (2) | 0.060 (3) | 0.039 (2) | 0.003 (2) | −0.0001 (17) | −0.0061 (18) |
C5 | 0.036 (2) | 0.046 (2) | 0.048 (2) | −0.0014 (18) | 0.0063 (18) | −0.0098 (18) |
C6 | 0.052 (3) | 0.065 (3) | 0.042 (2) | −0.004 (2) | 0.007 (2) | −0.017 (2) |
C7 | 0.049 (3) | 0.073 (3) | 0.065 (3) | 0.016 (2) | −0.007 (2) | −0.006 (2) |
C8 | 0.055 (3) | 0.075 (3) | 0.067 (3) | −0.019 (2) | 0.020 (2) | −0.011 (2) |
C9 | 0.074 (3) | 0.049 (3) | 0.080 (3) | 0.011 (2) | 0.004 (3) | 0.017 (2) |
Geometric parameters (Å, º) top
Sn1—C8 | 2.099 (4) | C2—H2 | 0.9300 |
Sn1—C9 | 2.112 (4) | C3—C4 | 1.391 (5) |
Sn1—C7 | 2.113 (4) | C4—C5 | 1.373 (5) |
Sn1—O1 | 2.187 (2) | C4—H4 | 0.9300 |
Sn1—O3 | 2.412 (3) | C5—C6 | 1.370 (5) |
Sn1—O2 | 3.103 (3) | C6—H6 | 0.9300 |
Br1—C5 | 1.894 (4) | C7—H7A | 0.9600 |
N1—C6 | 1.336 (5) | C7—H7B | 0.9600 |
N1—C2 | 1.336 (5) | C7—H7C | 0.9600 |
O1—C1 | 1.267 (5) | C8—H8A | 0.9600 |
O2—C1 | 1.233 (5) | C8—H8B | 0.9600 |
O3—H1 | 0.8500 | C8—H8C | 0.9600 |
O3—H3 | 0.8500 | C9—H9A | 0.9600 |
C1—C3 | 1.513 (5) | C9—H9B | 0.9600 |
C2—C3 | 1.368 (5) | C9—H9C | 0.9600 |
| | | |
C8—Sn1—C9 | 124.59 (19) | C4—C3—C1 | 120.2 (3) |
C8—Sn1—C7 | 117.78 (19) | C5—C4—C3 | 117.5 (4) |
C9—Sn1—C7 | 116.08 (19) | C5—C4—H4 | 121.3 |
C8—Sn1—O1 | 96.13 (14) | C3—C4—H4 | 121.3 |
C9—Sn1—O1 | 94.61 (16) | C6—C5—C4 | 120.1 (4) |
C7—Sn1—O1 | 91.45 (14) | C6—C5—Br1 | 119.5 (3) |
C8—Sn1—O3 | 82.17 (13) | C4—C5—Br1 | 120.4 (3) |
C9—Sn1—O3 | 87.22 (16) | N1—C6—C5 | 122.8 (3) |
C7—Sn1—O3 | 88.44 (14) | N1—C6—H6 | 118.6 |
O1—Sn1—O3 | 178.01 (11) | C5—C6—H6 | 118.6 |
C8—Sn1—O2 | 73.76 (15) | Sn1—C7—H7A | 109.5 |
C9—Sn1—O2 | 76.20 (15) | Sn1—C7—H7B | 109.5 |
C7—Sn1—O2 | 136.95 (13) | H7A—C7—H7B | 109.5 |
O1—Sn1—O2 | 45.54 (9) | Sn1—C7—H7C | 109.5 |
O3—Sn1—O2 | 134.48 (9) | H7A—C7—H7C | 109.5 |
C6—N1—C2 | 117.0 (4) | H7B—C7—H7C | 109.5 |
C1—O1—Sn1 | 116.7 (2) | Sn1—C8—H8A | 109.5 |
C1—O2—Sn1 | 72.8 (2) | Sn1—C8—H8B | 109.5 |
Sn1—O3—H1 | 120.7 | H8A—C8—H8B | 109.5 |
Sn1—O3—H3 | 111.3 | Sn1—C8—H8C | 109.5 |
H1—O3—H3 | 106.8 | H8A—C8—H8C | 109.5 |
O2—C1—O1 | 124.7 (4) | H8B—C8—H8C | 109.5 |
O2—C1—C3 | 119.5 (4) | Sn1—C9—H9A | 109.5 |
O1—C1—C3 | 115.8 (3) | Sn1—C9—H9B | 109.5 |
N1—C2—C3 | 123.7 (4) | H9A—C9—H9B | 109.5 |
N1—C2—H2 | 118.2 | Sn1—C9—H9C | 109.5 |
C3—C2—H2 | 118.2 | H9A—C9—H9C | 109.5 |
C2—C3—C4 | 118.9 (3) | H9B—C9—H9C | 109.5 |
C2—C3—C1 | 120.9 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N1i | 0.85 | 2.01 | 2.849 (4) | 168 |
O3—H1···O2ii | 0.85 | 1.84 | 2.684 (4) | 169 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, −z+1. |
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