Aqua­(5-bromido­nicotinato)trimethyl­tin(IV)

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	Block, colourless
Z = 8	0.38 × 0.27 × 0.21 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0224P)^2 + 2.0093P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (2)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1^i	0.85	2.01	2.849 (4)	168
O3—H1···O2^ii	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.