Aquadi-n-but-yl(5-methyl-pyrazine-2-carboxyl-ato)tin(IV) methanol solvate.

In the monomeric title compound, [Sn(C(4)H(9))(2)(C(6)H(5)N(2)O(2))(2)(H(2)O)]·CH(3)OH, the Sn atom is seven-coordinate, displaying a distorted penta-gonal bipyramidal SnC(2)N(2)O(3) geometry with the two C atoms in the axial sites. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the complex and solvent mol-ecules into infinite chains.

Related literature

For general background, see: Gielen et al. (1988 ▶). For a related structure, see: Ma et al. (2004 ▶).

Experimental

Crystal data

[Sn(C4H9)2(C6H5N2O2)2(H2O)]·CH4O

M = 557.21

Monoclinic,

a = 20.609 (5) Å

b = 17.119 (4) Å

c = 14.558 (3) Å

β = 98.178 (3)°

V = 5084 (2) Å3

Z = 8

Mo Kα radiation

μ = 1.05 mm−1

T = 298 (2) K

0.58 × 0.56 × 0.49 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.582, T max = 0.628

12959 measured reflections

4462 independent reflections

2981 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.122

S = 1.12

4462 reflections

289 parameters

12 restraints

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016140/hb2726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016140/hb2726Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C4H9)2(C6H5N2O2)2(H2O)]·CH4O	F000 = 2288
Mr = 557.21	Dx = 1.456 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4606 reflections
a = 20.609 (5) Å	θ = 2.4–25.3º
b = 17.119 (4) Å	µ = 1.05 mm−1
c = 14.558 (3) Å	T = 298 (2) K
β = 98.178 (3)º	Block, colourless
V = 5084 (2) Å3	0.58 × 0.56 × 0.49 mm
Z = 8

Bruker SMART CCD diffractometer	4462 independent reflections
Radiation source: fine-focus sealed tube	2981 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −15→24
Tmin = 0.582, Tmax = 0.628	k = −20→20
12959 measured reflections	l = −17→17

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0455P)2 + 11.2132P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.002
4462 reflections	Δρmax = 0.58 e Å−3
289 parameters	Δρmin = −0.67 e Å−3
12 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.256428 (17)	1.005653 (19)	0.41391 (2)	0.05022 (15)
N1	0.3679 (2)	0.9489 (2)	0.4509 (3)	0.0496 (10)
N2	0.4975 (2)	0.9001 (3)	0.4682 (4)	0.0746 (15)
N3	0.1453 (2)	1.0475 (3)	0.4696 (3)	0.0597 (12)
N4	0.0240 (3)	1.1105 (4)	0.4929 (4)	0.0858 (17)
O1	0.30863 (18)	1.0137 (2)	0.2956 (2)	0.0579 (9)
O2	0.4017 (2)	1.0160 (3)	0.2351 (3)	0.0784 (12)
O3	0.18771 (19)	1.0558 (2)	0.3031 (3)	0.0673 (11)
O4	0.09289 (19)	1.1052 (3)	0.2392 (3)	0.0757 (12)
O5	0.26009 (19)	0.9499 (2)	0.5931 (3)	0.0736 (11)
H1	0.2327	0.9135	0.5983	0.088*
H2	0.2730	0.9647	0.6484	0.088*
C1	0.3704 (3)	1.0012 (3)	0.2976 (4)	0.0529 (13)
C2	0.4039 (3)	0.9618 (3)	0.3833 (4)	0.0513 (13)
C3	0.4686 (3)	0.9380 (4)	0.3940 (4)	0.0679 (16)
H3	0.4932	0.9491	0.3467	0.082*
C4	0.4612 (3)	0.8866 (3)	0.5350 (4)	0.0620 (15)
C5	0.3965 (3)	0.9124 (3)	0.5273 (4)	0.0591 (14)
H5	0.3727	0.9042	0.5762	0.071*
C6	0.4918 (3)	0.8426 (4)	0.6191 (4)	0.090 (2)
H6A	0.5364	0.8300	0.6129	0.135*
H6B	0.4677	0.7953	0.6250	0.135*
H6C	0.4910	0.8743	0.6733	0.135*
C7	0.1295 (3)	1.0804 (3)	0.3063 (4)	0.0586 (14)
C8	0.1057 (3)	1.0790 (3)	0.3989 (4)	0.0532 (13)
C9	0.0454 (3)	1.1085 (4)	0.4106 (5)	0.0747 (18)
H9	0.0183	1.1279	0.3591	0.090*
C10	0.0627 (3)	1.0788 (4)	0.5628 (5)	0.0722 (17)
C11	0.1233 (3)	1.0474 (4)	0.5517 (4)	0.0729 (17)
H11	0.1492	1.0256	0.6027	0.087*
C12	0.0393 (4)	1.0786 (5)	0.6554 (5)	0.103 (3)
H12A	−0.0033	1.1022	0.6499	0.155*
H12B	0.0694	1.1076	0.6989	0.155*
H12C	0.0368	1.0258	0.6767	0.155*
C13	0.2915 (4)	1.1117 (4)	0.4756 (5)	0.091 (2)
H13A	0.3165	1.1364	0.4319	0.110*
H13B	0.2532	1.1442	0.4778	0.110*
C14	0.3295 (5)	1.1185 (4)	0.5624 (6)	0.128 (3)
H14A	0.3671	1.0843	0.5633	0.153*
H14B	0.3038	1.0990	0.6084	0.153*
C15	0.3547 (4)	1.1996 (4)	0.5931 (7)	0.111 (3)
H15A	0.3814	1.2197	0.5488	0.133*
H15B	0.3178	1.2346	0.5938	0.133*
C16	0.3937 (5)	1.1977 (5)	0.6860 (7)	0.139 (4)
H16A	0.4091	1.2494	0.7029	0.208*
H16B	0.4305	1.1634	0.6854	0.208*
H16C	0.3670	1.1792	0.7303	0.208*
C17	0.2167 (3)	0.8926 (3)	0.3962 (4)	0.0697 (17)
H17A	0.2404	0.8590	0.4431	0.084*
H17B	0.1716	0.8946	0.4079	0.084*
C18	0.2177 (4)	0.8561 (4)	0.3060 (5)	0.107 (3)
H18A	0.2627	0.8497	0.2950	0.129*
H18B	0.1955	0.8895	0.2577	0.129*
C19	0.1832 (6)	0.7749 (5)	0.3022 (7)	0.148 (4)
H19A	0.2050	0.7431	0.3525	0.178*
H19B	0.1384	0.7826	0.3133	0.178*
C20	0.1821 (7)	0.7340 (7)	0.2212 (9)	0.217 (7)
H20A	0.1597	0.6853	0.2258	0.326*
H20B	0.2262	0.7240	0.2103	0.326*
H20C	0.1596	0.7640	0.1707	0.326*
C21	0.1267 (4)	0.7823 (4)	0.5608 (5)	0.104 (3)
H21A	0.1147	0.7483	0.6081	0.156*
H21B	0.1551	0.7550	0.5249	0.156*
H21C	0.0879	0.7986	0.5210	0.156*
O6	0.1586 (3)	0.8466 (3)	0.6014 (4)	0.123 (2)
H6	0.1340	0.8703	0.6312	0.147*

	U11	U22	U33	U12	U13	U23
Sn1	0.0454 (2)	0.0530 (2)	0.0517 (2)	0.00077 (18)	0.00511 (16)	−0.00375 (17)
N1	0.048 (2)	0.050 (2)	0.051 (3)	0.001 (2)	0.006 (2)	−0.002 (2)
N2	0.057 (3)	0.092 (4)	0.074 (3)	0.017 (3)	0.004 (3)	0.000 (3)
N3	0.055 (3)	0.062 (3)	0.062 (3)	0.010 (2)	0.010 (2)	0.000 (2)
N4	0.066 (3)	0.111 (5)	0.084 (4)	0.014 (3)	0.024 (3)	0.010 (3)
O1	0.046 (2)	0.077 (2)	0.050 (2)	0.0019 (19)	0.0050 (17)	0.0063 (18)
O2	0.065 (3)	0.114 (3)	0.059 (3)	0.007 (2)	0.018 (2)	0.018 (2)
O3	0.056 (2)	0.088 (3)	0.058 (2)	0.019 (2)	0.0097 (19)	0.005 (2)
O4	0.057 (2)	0.110 (3)	0.058 (3)	0.018 (2)	0.002 (2)	0.011 (2)
O5	0.072 (3)	0.078 (3)	0.069 (3)	−0.014 (2)	0.003 (2)	0.000 (2)
C1	0.053 (3)	0.058 (3)	0.047 (3)	0.001 (3)	0.007 (3)	−0.003 (3)
C2	0.049 (3)	0.056 (3)	0.049 (3)	0.004 (3)	0.006 (3)	−0.007 (2)
C3	0.061 (4)	0.083 (4)	0.061 (4)	0.012 (3)	0.012 (3)	−0.006 (3)
C4	0.061 (4)	0.058 (3)	0.063 (4)	0.009 (3)	−0.005 (3)	−0.001 (3)
C5	0.058 (4)	0.064 (3)	0.054 (3)	−0.002 (3)	0.002 (3)	−0.007 (3)
C6	0.087 (5)	0.103 (5)	0.077 (5)	0.022 (4)	0.000 (4)	0.009 (4)
C7	0.051 (3)	0.063 (3)	0.060 (4)	0.000 (3)	0.001 (3)	−0.004 (3)
C8	0.048 (3)	0.054 (3)	0.058 (3)	0.002 (3)	0.007 (3)	−0.004 (3)
C9	0.052 (4)	0.096 (5)	0.075 (4)	0.011 (3)	0.006 (3)	0.009 (4)
C10	0.072 (4)	0.076 (4)	0.073 (4)	0.006 (4)	0.024 (4)	0.002 (3)
C11	0.074 (4)	0.082 (4)	0.062 (4)	0.016 (4)	0.010 (3)	0.001 (3)
C12	0.101 (6)	0.129 (7)	0.090 (5)	0.021 (5)	0.048 (5)	0.011 (5)
C13	0.122 (6)	0.059 (4)	0.084 (5)	0.006 (4)	−0.020 (5)	−0.013 (3)
C14	0.136 (8)	0.087 (6)	0.148 (8)	−0.019 (5)	−0.023 (7)	−0.027 (5)
C15	0.102 (6)	0.070 (5)	0.157 (8)	−0.022 (4)	0.007 (6)	−0.034 (5)
C16	0.165 (10)	0.097 (6)	0.153 (9)	−0.007 (6)	0.016 (8)	−0.028 (6)
C17	0.071 (4)	0.053 (3)	0.083 (4)	−0.013 (3)	0.005 (3)	−0.003 (3)
C18	0.131 (7)	0.083 (5)	0.108 (6)	−0.028 (5)	0.021 (5)	−0.037 (4)
C19	0.191 (11)	0.111 (7)	0.142 (9)	−0.040 (7)	0.023 (8)	−0.055 (6)
C20	0.265 (17)	0.138 (10)	0.244 (16)	−0.054 (11)	0.022 (13)	−0.074 (11)
C21	0.115 (6)	0.093 (5)	0.107 (6)	−0.020 (5)	0.028 (5)	−0.019 (5)
O6	0.118 (4)	0.129 (4)	0.134 (4)	−0.045 (4)	0.065 (3)	−0.047 (3)

Sn1—C17	2.103 (5)	C10—C12	1.494 (9)
Sn1—C13	2.107 (6)	C11—H11	0.9300
Sn1—O1	2.161 (4)	C12—H12A	0.9600
Sn1—O3	2.167 (4)	C12—H12B	0.9600
Sn1—N1	2.481 (4)	C12—H12C	0.9600
Sn1—N3	2.635 (5)	C13—C14	1.392 (9)
Sn1—O5	2.770 (4)	C13—H13A	0.9700
N1—C2	1.331 (6)	C13—H13B	0.9700
N1—C5	1.337 (6)	C14—C15	1.526 (8)
N2—C3	1.326 (7)	C14—H14A	0.9700
N2—C4	1.330 (8)	C14—H14B	0.9700
N3—C8	1.333 (6)	C15—C16	1.473 (10)
N3—C11	1.337 (7)	C15—H15A	0.9700
N4—C10	1.317 (8)	C15—H15B	0.9700
N4—C9	1.334 (8)	C16—H16A	0.9600
O1—C1	1.288 (6)	C16—H16B	0.9600
O2—C1	1.215 (7)	C16—H16C	0.9600
O3—C7	1.278 (6)	C17—C18	1.456 (8)
O4—C7	1.223 (6)	C17—H17A	0.9700
O5—H2	0.8500	C17—H17B	0.9700
O5—H1	0.8500	C18—C19	1.558 (9)
C1—C2	1.498 (7)	C18—H18A	0.9700
C2—C3	1.383 (7)	C18—H18B	0.9700
C3—H3	0.9300	C19—C20	1.369 (11)
C4—C5	1.395 (8)	C19—H19A	0.9700
C4—C6	1.498 (8)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6A	0.9600	C20—H20B	0.9600
C6—H6B	0.9600	C20—H20C	0.9600
C6—H6C	0.9600	C21—O6	1.372 (8)
C7—C8	1.498 (8)	C21—H21A	0.9600
C8—C9	1.376 (8)	C21—H21B	0.9600
C9—H9	0.9300	C21—H21C	0.9600
C10—C11	1.390 (8)	O6—H6	0.8200
C17—Sn1—C13	161.7 (3)	N4—C10—C12	117.4 (6)
C17—Sn1—O1	100.9 (2)	C11—C10—C12	121.0 (6)
C13—Sn1—O1	96.1 (2)	N3—C11—C10	121.9 (6)
C17—Sn1—O3	94.1 (2)	N3—C11—H11	119.0
C13—Sn1—O3	97.1 (2)	C10—C11—H11	119.0
O1—Sn1—O3	74.24 (14)	C10—C12—H12A	109.5
C17—Sn1—N1	89.9 (2)	C10—C12—H12B	109.5
C13—Sn1—N1	89.6 (2)	H12A—C12—H12B	109.5
O1—Sn1—N1	69.34 (14)	C10—C12—H12C	109.5
O3—Sn1—N1	143.46 (14)	H12A—C12—H12C	109.5
C17—Sn1—N3	87.0 (2)	H12B—C12—H12C	109.5
C13—Sn1—N3	84.0 (2)	C14—C13—Sn1	125.0 (5)
O1—Sn1—N3	141.33 (14)	C14—C13—H13A	106.1
O3—Sn1—N3	67.44 (15)	Sn1—C13—H13A	106.1
N1—Sn1—N3	149.10 (14)	C14—C13—H13B	106.1
C17—Sn1—O5	75.89 (18)	Sn1—C13—H13B	106.1
C13—Sn1—O5	86.2 (2)	H13A—C13—H13B	106.3
O1—Sn1—O5	145.38 (13)	C13—C14—C15	117.7 (7)
O3—Sn1—O5	139.93 (13)	C13—C14—H14A	107.9
N1—Sn1—O5	76.15 (13)	C15—C14—H14A	107.9
N3—Sn1—O5	73.29 (13)	C13—C14—H14B	107.9
C2—N1—C5	117.8 (5)	C15—C14—H14B	107.9
C2—N1—Sn1	111.8 (3)	H14A—C14—H14B	107.2
C5—N1—Sn1	130.4 (4)	C16—C15—C14	111.6 (7)
C3—N2—C4	116.5 (5)	C16—C15—H15A	109.3
C8—N3—C11	116.3 (5)	C14—C15—H15A	109.3
C8—N3—Sn1	109.6 (3)	C16—C15—H15B	109.3
C11—N3—Sn1	134.0 (4)	C14—C15—H15B	109.3
C10—N4—C9	116.3 (6)	H15A—C15—H15B	108.0
C1—O1—Sn1	125.1 (3)	C15—C16—H16A	109.5
C7—O3—Sn1	128.4 (4)	C15—C16—H16B	109.5
H2—O5—Sn1	138.8	H16A—C16—H16B	109.5
Sn1—O5—H1	113.9	C15—C16—H16C	109.5
Sn1—O5—H2	138.8	H16A—C16—H16C	109.5
H1—O5—H2	105.0	H16B—C16—H16C	109.5
O2—C1—O1	125.3 (5)	C18—C17—Sn1	116.8 (4)
O2—C1—C2	119.2 (5)	C18—C17—H17A	108.1
O1—C1—C2	115.5 (5)	Sn1—C17—H17A	108.1
N1—C2—C3	119.9 (5)	C18—C17—H17B	108.1
N1—C2—C1	116.8 (5)	Sn1—C17—H17B	108.1
C3—C2—C1	123.3 (5)	H17A—C17—H17B	107.3
N2—C3—C2	123.4 (6)	C17—C18—C19	110.5 (6)
N2—C3—H3	118.3	C17—C18—H18A	109.6
C2—C3—H3	118.3	C19—C18—H18A	109.6
N2—C4—C5	121.1 (5)	C17—C18—H18B	109.6
N2—C4—C6	118.0 (5)	C19—C18—H18B	109.6
C5—C4—C6	120.9 (6)	H18A—C18—H18B	108.1
N1—C5—C4	121.2 (6)	C20—C19—C18	116.0 (9)
N1—C5—H5	119.4	C20—C19—H19A	108.3
C4—C5—H5	119.4	C18—C19—H19A	108.3
C4—C6—H6A	109.5	C20—C19—H19B	108.3
C4—C6—H6B	109.5	C18—C19—H19B	108.3
H6A—C6—H6B	109.5	H19A—C19—H19B	107.4
C4—C6—H6C	109.5	C19—C20—H20A	109.5
H6A—C6—H6C	109.5	C19—C20—H20B	109.5
H6B—C6—H6C	109.5	H20A—C20—H20B	109.5
O4—C7—O3	124.2 (6)	C19—C20—H20C	109.5
O4—C7—C8	118.7 (5)	H20A—C20—H20C	109.5
O3—C7—C8	117.2 (5)	H20B—C20—H20C	109.5
N3—C8—C9	121.1 (5)	O6—C21—H21A	109.5
N3—C8—C7	117.3 (5)	O6—C21—H21B	109.5
C9—C8—C7	121.6 (5)	H21A—C21—H21B	109.5
N4—C9—C8	122.8 (6)	O6—C21—H21C	109.5
N4—C9—H9	118.6	H21A—C21—H21C	109.5
C8—C9—H9	118.6	H21B—C21—H21C	109.5
N4—C10—C11	121.6 (6)	C21—O6—H6	109.3

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O6	0.85	1.92	2.755 (6)	169
O5—H2···O1i	0.85	2.19	3.039 (5)	172
O6—H6···O4i	0.82	1.93	2.703 (6)	156

Table 1

Selected bond lengths (Å)

Sn1—C17	2.103 (5)
Sn1—C13	2.107 (6)
Sn1—O1	2.161 (4)
Sn1—O3	2.167 (4)
Sn1—N1	2.481 (4)
Sn1—N3	2.635 (5)
Sn1—O5	2.770 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O6	0.85	1.92	2.755 (6)	169
O5—H2⋯O1i	0.85	2.19	3.039 (5)	172
O6—H6⋯O4i	0.82	1.93	2.703 (6)	156

Symmetry code: (i) .