(2-{[1,1-Bis(hy­droxy­meth­yl)-2-oxidoeth­yl]imino­meth­yl}-4-chloro­phenolato-κ3O,N,O′)dibutyl­tin(IV)

Lee, S.M.; Mohd Ali, H.; Lo, K.M.

doi:10.1107/S1600536810021872

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m793

doi:10.1107/S1600536810021872

Open

access

(2-{[1,1-Bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-4-chlorophenolato-κ³O,N,O′)dibutyltin(IV)

See Mun Lee,^a Hapipah Mohd Ali ^a and Kong Mun Lo ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: kmlo@um.edu.my

(Received 27 May 2010; accepted 8 June 2010; online 16 June 2010)

In the title compound, [Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)], the Schiff base ligand chelates to the Sn^IV atom through the two deprotonated hydroxy groups, as well as through the N atom, to confer an overall cis-C₂SnNO₂ trigonal-bipyramidal geometry at the Sn^IV atom [C—Sn—C = 129.92 (9)°]. The remaining methylenehydroxy groups engage in O—H⋯O hydrogen bonding with the O atoms of adjacent molecules, leading to infinite supramolecular chains propagating in [001].

Related literature

For related structures, see Reisi et al. (2010 ); Ng (2008 ).

Experimental

Crystal data

[Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)]
M_r = 535.04
Monoclinic, C 2/c
a = 18.8326 (9) Å
b = 13.3811 (7) Å
c = 16.5768 (8) Å
β = 91.385 (3)°
V = 4176.1 (4) Å³
Z = 8
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.365, T_max = 0.786
19535 measured reflections
4785 independent reflections
4229 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.052
S = 1.02
4785 reflections
239 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—N1	2.2108 (17)
Sn1—O1	2.1203 (15)
Sn1—O2	2.1049 (14)
Sn1—C12	2.139 (2)
Sn1—C16	2.129 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84	1.77	2.608 (2)	174
O4—H4⋯O3ⁱⁱ	0.84	1.93	2.733 (2)	160
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: pubCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021872/xu2772sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021872/xu2772Isup2.hkl

checkCIF report

Comment top

The Schiff base derived from the condensation of 5-bromosalicylaldehyde and tris(hydroxymethyl)methylamine is deprotonated with respect to the phenoxy hydrogen atom and one of the methylenehydroxyl hydrogen atom. The ligand coordinates to the dibutyltin fragment through this doubly deprotonated oxygen atoms and the imine nitrogen (Fig. 1).

The tin atom is in a cis-trigonal bipyramidal geometry with a C—Sn—C angle of 129.92 (9)°. The two deprotonated oxygen atoms occupied the axial sites with a O—Sn—O angle of 155.60 (6)°, indicating a distortion in the trigonal bipyramidal geometry at the Sn atom. Adjacent molecules are linked by hydrogen bonds to form an infinite polymeric chain (Fig. 2).

Related literature top

For related structures, see Reisi et al. (2010); Ng (2008).

Experimental top

The Schiff base, 4-bromo-2-tris[(hydroxymethyl)methylimino]phenol was prepared from tris(hydroxymethyl)aminomethane and 5-bromosalicylaldehyde in absolute ethanol. The compound (0.30 g, 0.1 mmol) and dibutyltin oxide (0.25 g, 1.0 mmol) were heated in 50 ml of toluene in a Dean-Stark apparatus for 8 h. The solution was left for crystallizaton for a week during which yellow crystals were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (2-{[1,1-bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-4-chlorophenolato-κ³N,O,O')dibutyltin(IV) showing 70% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Crystal packing of the unit cell showing the hydrogen bonding interactions in the molecule.

(2-{[1,1-Bis(hydroxymethyl)-2-oxidoethyl]iminomethyl}-4-chlorophenolato- κ³O,N,O')dibutyltin(IV) top

Crystal data top

[Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)]	F(000) = 2144
M_r = 535.04	D_x = 1.702 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7855 reflections
a = 18.8326 (9) Å	θ = 2.2–30.4°
b = 13.3811 (7) Å	µ = 3.16 mm⁻¹
c = 16.5768 (8) Å	T = 100 K
β = 91.385 (3)°	Needle, yellow
V = 4176.1 (4) Å³	0.40 × 0.10 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	4785 independent reflections
Radiation source: fine-focus sealed tube	4229 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
T_min = 0.365, T_max = 0.786	k = −17→17
19535 measured reflections	l = −21→21

Refinement top

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0231P)² + 4.784P] where P = (F_o² + 2F_c²)/3
4785 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.65 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)]	V = 4176.1 (4) Å³
M_r = 535.04	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.8326 (9) Å	µ = 3.16 mm⁻¹
b = 13.3811 (7) Å	T = 100 K
c = 16.5768 (8) Å	0.40 × 0.10 × 0.08 mm
β = 91.385 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4785 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4229 reflections with I > 2σ(I)
T_min = 0.365, T_max = 0.786	R_int = 0.032
19535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	2 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.02	Δρ_max = 0.65 e Å⁻³
4785 reflections	Δρ_min = −0.38 e Å⁻³
239 parameters

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	U_iso*/U_eq
Sn1	0.325854 (7)	0.128538 (10)	0.254101 (8)	0.01133 (5)
Br1	0.047899 (12)	0.180095 (17)	−0.072373 (14)	0.02090 (6)
N1	0.33348 (9)	0.06301 (13)	0.13219 (10)	0.0117 (3)
O1	0.27217 (8)	0.24249 (11)	0.18796 (9)	0.0154 (3)
O2	0.39697 (8)	0.00855 (11)	0.27086 (8)	0.0141 (3)
O3	0.51910 (7)	−0.01628 (11)	0.10327 (9)	0.0139 (3)
H3	0.5442	−0.0111	0.1456	0.021*
O4	0.37130 (8)	−0.06319 (12)	−0.01932 (8)	0.0151 (3)
H4	0.4107	−0.0416	−0.0344	0.023*
C1	0.22983 (11)	0.14839 (15)	0.07343 (12)	0.0119 (4)
C2	0.22471 (11)	0.22806 (16)	0.12949 (12)	0.0132 (4)
C3	0.16695 (12)	0.29422 (16)	0.12036 (12)	0.0153 (4)
H3A	0.1638	0.3502	0.1554	0.018*
C4	0.11478 (11)	0.27967 (17)	0.06175 (13)	0.0155 (4)
H4A	0.0751	0.3234	0.0581	0.019*
C5	0.12066 (11)	0.19991 (16)	0.00753 (12)	0.0148 (4)
C6	0.17791 (11)	0.13705 (16)	0.01159 (13)	0.0144 (4)
H6	0.1826	0.0856	−0.0274	0.017*
C7	0.28804 (11)	0.07801 (16)	0.07408 (12)	0.0125 (4)
H7	0.2933	0.0388	0.0268	0.015*
C8	0.39114 (11)	−0.01213 (15)	0.12512 (12)	0.0116 (4)
C9	0.39651 (11)	−0.06281 (16)	0.20865 (12)	0.0130 (4)
H9A	0.3557	−0.1085	0.2150	0.016*
H9B	0.4406	−0.1030	0.2124	0.016*
C10	0.45890 (10)	0.04737 (15)	0.10849 (12)	0.0117 (4)
H10A	0.4525	0.0847	0.0573	0.014*
H10B	0.4672	0.0966	0.1523	0.014*
C11	0.37745 (11)	−0.09448 (16)	0.06228 (12)	0.0131 (4)
H11A	0.4167	−0.1436	0.0668	0.016*
H11B	0.3331	−0.1296	0.0762	0.016*
C12	0.23527 (12)	0.06420 (17)	0.30964 (14)	0.0191 (5)
H12A	0.2208	0.0044	0.2781	0.023*
H12B	0.2500	0.0410	0.3642	0.023*
C13	0.17028 (12)	0.13118 (19)	0.31788 (16)	0.0259 (5)
H13A	0.1816	0.1846	0.3574	0.031*
H13B	0.1597	0.1635	0.2652	0.031*
C14	0.10488 (13)	0.07612 (19)	0.34454 (17)	0.0272 (5)
H14A	0.1168	0.0397	0.3951	0.033*
H14B	0.0918	0.0258	0.3030	0.033*
C15	0.04070 (14)	0.1421 (2)	0.35880 (18)	0.0350 (7)
H15A	0.0495	0.1833	0.4069	0.052*
H15B	−0.0012	0.1001	0.3669	0.052*
H15C	0.0323	0.1854	0.3119	0.052*
C16	0.40219 (11)	0.23185 (17)	0.30125 (13)	0.0164 (4)
H16A	0.4161	0.2102	0.3565	0.020*
H16B	0.4451	0.2276	0.2680	0.020*
C17	0.37945 (12)	0.34137 (17)	0.30495 (14)	0.0180 (5)
H17A	0.4205	0.3818	0.3243	0.022*
H17B	0.3667	0.3641	0.2496	0.022*
C18	0.31701 (12)	0.36167 (17)	0.35918 (14)	0.0200 (5)
H18A	0.3050	0.4336	0.3560	0.024*
H18B	0.2753	0.3237	0.3385	0.024*
C19	0.33061 (15)	0.3340 (2)	0.44694 (15)	0.0344 (7)
H19A	0.3368	0.2615	0.4515	0.052*
H19B	0.2901	0.3549	0.4789	0.052*
H19C	0.3737	0.3677	0.4671	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.00935 (7)	0.01444 (8)	0.01012 (7)	0.00111 (5)	−0.00151 (5)	−0.00132 (5)
Br1	0.01670 (11)	0.02112 (12)	0.02432 (12)	0.00431 (9)	−0.01116 (9)	−0.00292 (9)
N1	0.0092 (8)	0.0119 (8)	0.0140 (8)	0.0008 (7)	0.0000 (6)	0.0013 (7)
O1	0.0171 (8)	0.0148 (7)	0.0139 (7)	0.0022 (6)	−0.0048 (6)	−0.0024 (6)
O2	0.0146 (7)	0.0160 (7)	0.0116 (7)	0.0034 (6)	−0.0035 (6)	−0.0013 (6)
O3	0.0092 (7)	0.0196 (8)	0.0127 (7)	0.0046 (6)	−0.0028 (6)	−0.0026 (6)
O4	0.0133 (7)	0.0214 (8)	0.0107 (7)	−0.0014 (6)	0.0005 (6)	−0.0005 (6)
C1	0.0097 (9)	0.0143 (10)	0.0117 (10)	0.0006 (8)	−0.0013 (8)	0.0013 (8)
C2	0.0128 (10)	0.0164 (10)	0.0105 (9)	−0.0011 (8)	0.0001 (8)	0.0010 (8)
C3	0.0185 (11)	0.0149 (10)	0.0126 (10)	0.0024 (9)	0.0015 (8)	−0.0015 (8)
C4	0.0131 (10)	0.0190 (11)	0.0144 (10)	0.0034 (9)	0.0003 (8)	0.0031 (8)
C5	0.0117 (10)	0.0188 (11)	0.0138 (10)	−0.0011 (9)	−0.0042 (8)	0.0028 (8)
C6	0.0140 (10)	0.0154 (10)	0.0136 (10)	0.0012 (8)	−0.0023 (8)	−0.0004 (8)
C7	0.0119 (10)	0.0128 (10)	0.0129 (10)	−0.0002 (8)	0.0018 (8)	0.0001 (8)
C8	0.0096 (9)	0.0127 (10)	0.0124 (10)	0.0032 (8)	−0.0003 (7)	0.0003 (8)
C9	0.0120 (10)	0.0141 (10)	0.0128 (10)	0.0027 (8)	−0.0009 (8)	0.0001 (8)
C10	0.0095 (9)	0.0140 (10)	0.0114 (10)	0.0009 (8)	−0.0010 (7)	−0.0002 (8)
C11	0.0110 (9)	0.0144 (10)	0.0138 (10)	−0.0006 (8)	−0.0008 (8)	−0.0009 (8)
C12	0.0155 (11)	0.0192 (11)	0.0227 (12)	−0.0013 (9)	0.0043 (9)	−0.0017 (9)
C13	0.0166 (12)	0.0316 (14)	0.0298 (13)	0.0049 (10)	0.0043 (10)	0.0099 (11)
C14	0.0196 (12)	0.0264 (13)	0.0359 (14)	−0.0035 (11)	0.0077 (10)	−0.0110 (11)
C15	0.0179 (13)	0.0498 (18)	0.0376 (16)	0.0035 (12)	0.0062 (11)	0.0078 (13)
C16	0.0115 (10)	0.0193 (11)	0.0183 (11)	0.0024 (9)	−0.0016 (8)	−0.0034 (9)
C17	0.0177 (11)	0.0174 (11)	0.0188 (11)	−0.0003 (9)	−0.0035 (9)	−0.0014 (9)
C18	0.0201 (11)	0.0197 (11)	0.0199 (11)	0.0051 (9)	−0.0042 (9)	−0.0049 (9)
C19	0.0313 (14)	0.0536 (18)	0.0184 (12)	0.0169 (14)	0.0004 (11)	0.0000 (12)

Geometric parameters (Å, º) top

Sn1—N1	2.2108 (17)	C9—H9B	0.9900
Sn1—O1	2.1203 (15)	C10—H10A	0.9900
Sn1—O2	2.1049 (14)	C10—H10B	0.9900
Sn1—C12	2.139 (2)	C11—H11A	0.9900
Sn1—C16	2.129 (2)	C11—H11B	0.9900
Br1—C5	1.901 (2)	C12—C13	1.526 (3)
N1—C7	1.289 (3)	C12—H12A	0.9900
N1—C8	1.487 (3)	C12—H12B	0.9900
O1—C2	1.317 (2)	C13—C14	1.510 (3)
O2—C9	1.405 (2)	C13—H13A	0.9900
O3—C10	1.422 (2)	C13—H13B	0.9900
O3—H3	0.8400	C14—C15	1.520 (3)
O4—C11	1.418 (2)	C14—H14A	0.9900
O4—H4	0.8400	C14—H14B	0.9900
C1—C6	1.408 (3)	C15—H15A	0.9800
C1—C2	1.419 (3)	C15—H15B	0.9800
C1—C7	1.445 (3)	C15—H15C	0.9800
C2—C3	1.408 (3)	C16—C17	1.528 (3)
C3—C4	1.379 (3)	C16—H16A	0.9900
C3—H3A	0.9500	C16—H16B	0.9900
C4—C5	1.401 (3)	C17—C18	1.522 (3)
C4—H4A	0.9500	C17—H17A	0.9900
C5—C6	1.368 (3)	C17—H17B	0.9900
C6—H6	0.9500	C18—C19	1.517 (3)
C7—H7	0.9500	C18—H18A	0.9900
C8—C11	1.534 (3)	C18—H18B	0.9900
C8—C10	1.535 (3)	C19—H19A	0.9800
C8—C9	1.543 (3)	C19—H19B	0.9800
C9—H9A	0.9900	C19—H19C	0.9800

O2—Sn1—O1	155.60 (6)	H10A—C10—H10B	108.0
O2—Sn1—C16	91.43 (7)	O4—C11—C8	116.38 (17)
O1—Sn1—C16	91.84 (7)	O4—C11—H11A	108.2
O2—Sn1—C12	98.49 (7)	C8—C11—H11A	108.2
O1—Sn1—C12	97.86 (8)	O4—C11—H11B	108.2
C16—Sn1—C12	129.92 (9)	C8—C11—H11B	108.2
O2—Sn1—N1	76.29 (6)	H11A—C11—H11B	107.3
O1—Sn1—N1	81.56 (6)	C13—C12—Sn1	116.87 (16)
C16—Sn1—N1	122.33 (7)	C13—C12—H12A	108.1
C12—Sn1—N1	107.69 (8)	Sn1—C12—H12A	108.1
C7—N1—C8	121.31 (18)	C13—C12—H12B	108.1
C7—N1—Sn1	124.39 (14)	Sn1—C12—H12B	108.1
C8—N1—Sn1	113.83 (12)	H12A—C12—H12B	107.3
C2—O1—Sn1	125.58 (13)	C14—C13—C12	113.7 (2)
C9—O2—Sn1	115.39 (12)	C14—C13—H13A	108.8
C10—O3—H3	109.5	C12—C13—H13A	108.8
C11—O4—H4	109.5	C14—C13—H13B	108.8
C6—C1—C2	120.06 (19)	C12—C13—H13B	108.8
C6—C1—C7	116.66 (19)	H13A—C13—H13B	107.7
C2—C1—C7	123.25 (19)	C13—C14—C15	114.8 (2)
O1—C2—C3	119.74 (19)	C13—C14—H14A	108.6
O1—C2—C1	122.45 (19)	C15—C14—H14A	108.6
C3—C2—C1	117.81 (19)	C13—C14—H14B	108.6
C4—C3—C2	121.5 (2)	C15—C14—H14B	108.6
C4—C3—H3A	119.2	H14A—C14—H14B	107.5
C2—C3—H3A	119.2	C14—C15—H15A	109.5
C3—C4—C5	119.6 (2)	C14—C15—H15B	109.5
C3—C4—H4A	120.2	H15A—C15—H15B	109.5
C5—C4—H4A	120.2	C14—C15—H15C	109.5
C6—C5—C4	120.8 (2)	H15A—C15—H15C	109.5
C6—C5—Br1	120.16 (16)	H15B—C15—H15C	109.5
C4—C5—Br1	119.09 (16)	C17—C16—Sn1	116.73 (14)
C5—C6—C1	120.2 (2)	C17—C16—H16A	108.1
C5—C6—H6	119.9	Sn1—C16—H16A	108.1
C1—C6—H6	119.9	C17—C16—H16B	108.1
N1—C7—C1	126.66 (19)	Sn1—C16—H16B	108.1
N1—C7—H7	116.7	H16A—C16—H16B	107.3
C1—C7—H7	116.7	C18—C17—C16	114.59 (19)
N1—C8—C11	115.35 (16)	C18—C17—H17A	108.6
N1—C8—C10	105.98 (16)	C16—C17—H17A	108.6
C11—C8—C10	112.19 (16)	C18—C17—H17B	108.6
N1—C8—C9	104.99 (15)	C16—C17—H17B	108.6
C11—C8—C9	107.46 (17)	H17A—C17—H17B	107.6
C10—C8—C9	110.64 (16)	C19—C18—C17	114.1 (2)
O2—C9—C8	111.04 (17)	C19—C18—H18A	108.7
O2—C9—H9A	109.4	C17—C18—H18A	108.7
C8—C9—H9A	109.4	C19—C18—H18B	108.7
O2—C9—H9B	109.4	C17—C18—H18B	108.7
C8—C9—H9B	109.4	H18A—C18—H18B	107.6
H9A—C9—H9B	108.0	C18—C19—H19A	109.5
O3—C10—C8	111.57 (16)	C18—C19—H19B	109.5
O3—C10—H10A	109.3	H19A—C19—H19B	109.5
C8—C10—H10A	109.3	C18—C19—H19C	109.5
O3—C10—H10B	109.3	H19A—C19—H19C	109.5
C8—C10—H10B	109.3	H19B—C19—H19C	109.5

O2—Sn1—N1—C7	161.51 (18)	Sn1—N1—C7—C1	8.4 (3)
O1—Sn1—N1—C7	−28.79 (17)	C6—C1—C7—N1	−166.4 (2)
C16—Sn1—N1—C7	−115.61 (17)	C2—C1—C7—N1	15.8 (3)
C12—Sn1—N1—C7	66.82 (18)	C7—N1—C8—C11	−22.0 (3)
O2—Sn1—N1—C8	−10.66 (12)	Sn1—N1—C8—C11	150.45 (14)
O1—Sn1—N1—C8	159.04 (14)	C7—N1—C8—C10	102.8 (2)
C16—Sn1—N1—C8	72.22 (15)	Sn1—N1—C8—C10	−84.77 (15)
C12—Sn1—N1—C8	−105.35 (14)	C7—N1—C8—C9	−140.06 (19)
O2—Sn1—O1—C2	67.9 (2)	Sn1—N1—C8—C9	32.38 (18)
C16—Sn1—O1—C2	165.50 (16)	Sn1—O2—C9—C8	41.10 (19)
C12—Sn1—O1—C2	−63.76 (17)	N1—C8—C9—O2	−46.7 (2)
N1—Sn1—O1—C2	43.07 (16)	C11—C8—C9—O2	−169.96 (16)
O1—Sn1—O2—C9	−42.4 (2)	C10—C8—C9—O2	67.3 (2)
C16—Sn1—O2—C9	−140.00 (14)	N1—C8—C10—O3	177.90 (15)
C12—Sn1—O2—C9	89.25 (14)	C11—C8—C10—O3	−55.4 (2)
N1—Sn1—O2—C9	−17.01 (13)	C9—C8—C10—O3	64.6 (2)
Sn1—O1—C2—C3	144.75 (16)	N1—C8—C11—O4	63.8 (2)
Sn1—O1—C2—C1	−36.3 (3)	C10—C8—C11—O4	−57.7 (2)
C6—C1—C2—O1	−179.37 (19)	C9—C8—C11—O4	−179.53 (16)
C7—C1—C2—O1	−1.7 (3)	O2—Sn1—C12—C13	174.84 (17)
C6—C1—C2—C3	−0.4 (3)	O1—Sn1—C12—C13	−23.33 (19)
C7—C1—C2—C3	177.28 (19)	C16—Sn1—C12—C13	75.8 (2)
O1—C2—C3—C4	−177.65 (19)	N1—Sn1—C12—C13	−106.93 (18)
C1—C2—C3—C4	3.4 (3)	Sn1—C12—C13—C14	170.31 (17)
C2—C3—C4—C5	−2.9 (3)	C12—C13—C14—C15	176.0 (2)
C3—C4—C5—C6	−0.7 (3)	O2—Sn1—C16—C17	−179.92 (16)
C3—C4—C5—Br1	179.46 (16)	O1—Sn1—C16—C17	24.26 (16)
C4—C5—C6—C1	3.6 (3)	C12—Sn1—C16—C17	−77.59 (19)
Br1—C5—C6—C1	−176.54 (16)	N1—Sn1—C16—C17	105.44 (16)
C2—C1—C6—C5	−3.0 (3)	Sn1—C16—C17—C18	62.2 (2)
C7—C1—C6—C5	179.12 (19)	C16—C17—C18—C19	60.7 (3)
C8—N1—C7—C1	179.97 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.77	2.608 (2)	174
O4—H4···O3ⁱⁱ	0.84	1.93	2.733 (2)	160

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Sn(C₄H₉)₂(C₁₁H₁₂BrNO₄)]
M_r	535.04
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.8326 (9), 13.3811 (7), 16.5768 (8)
β (°)	91.385 (3)
V (Å³)	4176.1 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.40 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.365, 0.786
No. of measured, independent and observed [I > 2σ(I)] reflections	19535, 4785, 4229
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.052, 1.02
No. of reflections	4785
No. of parameters	239
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2010).

Selected bond lengths (Å) top

Sn1—N1	2.2108 (17)	Sn1—C12	2.139 (2)
Sn1—O1	2.1203 (15)	Sn1—C16	2.129 (2)
Sn1—O2	2.1049 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84	1.77	2.608 (2)	173.9
O4—H4···O3ⁱⁱ	0.84	1.93	2.733 (2)	159.6

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1, −y, −z.

Acknowledgements

We thank the University of Malaya (grant Nos. PS342/2009 C and RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, S. W. (2008). Acta Cryst. E64, o2455. Web of Science CrossRef IUCr Journals Google Scholar
Reisi, R., Misran, M., Lo, K. M. & Ng, S. W. (2010). Acta Cryst. E66, m482. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.