(2-{[1,1-Bis(hy-droxy-meth-yl)-2-oxidoeth-yl]imino-meth-yl}-4-chloro-phenolato-κO,N,O')dibutyl-tin(IV).

In the title compound, [Sn(C(4)H(9))(2)(C(11)H(12)BrNO(4))], the Schiff base ligand chelates to the Sn(IV) atom through the two deprotonated hy-droxy groups, as well as through the N atom, to confer an overall cis-C(2)SnNO(2) trigonal-bipyramidal geometry at the Sn(IV) atom [C-Sn-C = 129.92 (9)°]. The remaining methyl-enehy-droxy groups engage in O-H⋯O hydrogen bonding with the O atoms of adjacent mol-ecules, leading to infinite supra-molecular chains propagating in [001].

Related literature

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

Experimental

Crystal data

[Sn(C4H9)2(C11H12BrNO4)]

M = 535.04

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.052

S = 1.02

4785 reflections

239 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

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

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

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

[Sn(C4H9)2(C11H12BrNO4)]	F(000) = 2144
Mr = 535.04	Dx = 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

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

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(Fo2) + (0.0231P)2 + 4.784P] where P = (Fo2 + 2Fc2)/3
4785 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.65 e Å−3
2 restraints	Δρmin = −0.37 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	0.325854 (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*

	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)

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)

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

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) ; (ii) .