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

The Schiff base ligand in the title compound, [Sn(C(4)H(9))(2)(C(11)H(12)ClNO(4))], chelates to the Sn atom through the two deprotonated O atoms, as well as through the N atom, to confer an overall cis-C(2)SnNO(2) trigonal-bipyramidal geometry at tin [C-Sn-C = 130.3 (1)°]. The hydr-oxy groups engage in O-H⋯O hydrogen bonding with the O atoms of adjacent mol-ecules, generating a chain running along the c axis.

Related literature

For the crystal structure of the uncoordinated Schiff base, see: Ng (2008 ▶).

Experimental

Crystal data

[Sn(C4H9)2(C11H12ClNO4)]

M = 490.58

Monoclinic,

a = 18.6212 (2) Å

b = 13.4657 (2) Å

c = 16.6949 (1) Å

β = 91.845 (1)°

V = 4184.03 (8) Å3

Z = 8

Mo Kα radiation

μ = 1.37 mm−1

T = 123 K

0.43 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.590, T max = 0.726

23501 measured reflections

4803 independent reflections

4350 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.064

S = 0.94

4803 reflections

243 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011384/bt5229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011384/bt5229Isup2.hkl

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

[Sn(C4H9)2(C11H12ClNO4)]	F(000) = 2000
Mr = 490.58	Dx = 1.558 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9381 reflections
a = 18.6212 (2) Å	θ = 2.2–31.7°
b = 13.4657 (2) Å	µ = 1.37 mm−1
c = 16.6949 (1) Å	T = 123 K
β = 91.845 (1)°	Block, yellow
V = 4184.03 (8) Å3	0.43 × 0.30 × 0.25 mm
Z = 8

Bruker SMART APEX diffractometer	4803 independent reflections
Radiation source: fine-focus sealed tube	4350 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.590, Tmax = 0.726	k = −15→17
23501 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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0487P)2 + 2.5005P] where P = (Fo2 + 2Fc2)/3
4803 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.60 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.324176 (5)	0.374067 (8)	0.254047 (6)	0.01818 (5)
Cl1	0.05353 (3)	0.31243 (4)	−0.07291 (3)	0.03821 (13)
N1	0.33156 (7)	0.43789 (10)	0.13234 (8)	0.0169 (3)
O1	0.26803 (7)	0.26136 (9)	0.18945 (7)	0.0251 (3)
O2	0.39660 (6)	0.49305 (9)	0.27014 (7)	0.0213 (2)
O3	0.51910 (6)	0.51554 (9)	0.10309 (7)	0.0208 (2)
O4	0.37037 (6)	0.56261 (10)	−0.01897 (7)	0.0233 (3)
C1	0.40248 (10)	0.27086 (14)	0.29943 (12)	0.0280 (4)
H1A	0.4452	0.2757	0.2658	0.034*
H1B	0.4175	0.2922	0.3542	0.034*
C2	0.38064 (11)	0.16181 (15)	0.30333 (12)	0.0318 (4)
H2A	0.3669	0.1391	0.2486	0.038*
H2B	0.4229	0.1224	0.3218	0.038*
C3	0.31878 (12)	0.14046 (16)	0.35828 (14)	0.0367 (5)
H3A	0.2761	0.1786	0.3392	0.044*
H3B	0.3066	0.0690	0.3546	0.044*
C4	0.33487 (16)	0.1662 (3)	0.44466 (15)	0.0629 (8)
H4A	0.2930	0.1507	0.4765	0.094*
H4B	0.3458	0.2372	0.4492	0.094*
H4C	0.3763	0.1276	0.4646	0.094*
C5	0.23412 (10)	0.43890 (15)	0.31046 (12)	0.0298 (4)
H5A	0.2499	0.4597	0.3651	0.036*
H5B	0.2204	0.4997	0.2804	0.036*
C6	0.16740 (12)	0.37495 (16)	0.31741 (16)	0.0403 (5)
H6A	0.1547	0.3469	0.2640	0.048*
H6B	0.1789	0.3187	0.3538	0.048*
C7	0.10287 (11)	0.42862 (17)	0.34800 (15)	0.0420 (5)
H7A	0.0889	0.4814	0.3092	0.050*
H7B	0.1168	0.4614	0.3993	0.050*
C8	0.03807 (14)	0.3637 (2)	0.36135 (19)	0.0559 (7)
H8A	−0.0008	0.4042	0.3822	0.084*
H8B	0.0509	0.3114	0.4000	0.084*
H8C	0.0221	0.3334	0.3104	0.084*
C9	0.22124 (9)	0.27459 (12)	0.12977 (9)	0.0194 (3)
C10	0.16258 (9)	0.20867 (13)	0.11998 (10)	0.0236 (3)
H10	0.1584	0.1544	0.1559	0.028*
C11	0.11135 (9)	0.22152 (14)	0.05944 (10)	0.0245 (4)
H11	0.0710	0.1785	0.0557	0.029*
C12	0.11877 (9)	0.29764 (13)	0.00376 (10)	0.0230 (3)
C13	0.17673 (10)	0.36033 (13)	0.00828 (11)	0.0229 (4)
H13	0.1826	0.4098	−0.0315	0.028*
C14	0.22784 (8)	0.35110 (13)	0.07241 (10)	0.0186 (3)
C15	0.28649 (8)	0.42135 (12)	0.07342 (10)	0.0181 (3)
H15	0.2925	0.4591	0.0261	0.022*
C16	0.38984 (8)	0.51236 (12)	0.12515 (9)	0.0159 (3)
C17	0.39581 (9)	0.56345 (12)	0.20768 (9)	0.0192 (3)
H17A	0.4404	0.6034	0.2112	0.023*
H17B	0.3546	0.6090	0.2136	0.023*
C18	0.45807 (8)	0.45272 (12)	0.10880 (10)	0.0180 (3)
H18A	0.4667	0.4042	0.1526	0.022*
H18B	0.4510	0.4152	0.0581	0.022*
C19	0.37587 (9)	0.59373 (13)	0.06223 (10)	0.0201 (3)
H19B	0.3307	0.6282	0.0752	0.024*
H19A	0.4152	0.6431	0.0674	0.024*
H3O	0.5441 (11)	0.5129 (19)	0.1452 (9)	0.043 (7)*
H4O	0.4099 (8)	0.5403 (17)	−0.0338 (13)	0.036 (6)*

	U11	U22	U33	U12	U13	U23
Sn1	0.01691 (8)	0.02207 (8)	0.01539 (8)	−0.00301 (4)	−0.00201 (5)	0.00291 (4)
Cl1	0.0319 (2)	0.0357 (3)	0.0454 (3)	−0.00971 (19)	−0.0231 (2)	0.0064 (2)
N1	0.0143 (6)	0.0188 (7)	0.0176 (6)	−0.0016 (5)	0.0002 (5)	0.0011 (5)
O1	0.0287 (6)	0.0245 (6)	0.0215 (6)	−0.0075 (5)	−0.0081 (5)	0.0056 (5)
O2	0.0235 (6)	0.0246 (6)	0.0157 (5)	−0.0051 (5)	−0.0039 (4)	0.0021 (5)
O3	0.0147 (5)	0.0293 (7)	0.0184 (6)	−0.0050 (4)	−0.0022 (4)	0.0037 (5)
O4	0.0210 (6)	0.0322 (7)	0.0165 (6)	0.0003 (5)	0.0003 (5)	0.0036 (5)
C1	0.0220 (8)	0.0282 (10)	0.0334 (10)	−0.0012 (7)	−0.0055 (7)	0.0062 (8)
C2	0.0328 (10)	0.0266 (10)	0.0355 (10)	0.0011 (8)	−0.0034 (8)	0.0027 (8)
C3	0.0356 (11)	0.0367 (11)	0.0372 (12)	−0.0116 (8)	−0.0060 (9)	0.0108 (9)
C4	0.0592 (17)	0.094 (2)	0.0357 (13)	−0.0296 (16)	−0.0015 (12)	0.0084 (14)
C5	0.0264 (9)	0.0296 (10)	0.0337 (10)	−0.0011 (7)	0.0066 (7)	−0.0002 (8)
C6	0.0269 (10)	0.0461 (14)	0.0485 (14)	−0.0077 (8)	0.0097 (9)	−0.0149 (10)
C7	0.0303 (10)	0.0395 (12)	0.0570 (14)	0.0044 (9)	0.0120 (10)	0.0132 (10)
C8	0.0296 (12)	0.080 (2)	0.0587 (17)	−0.0080 (11)	0.0091 (11)	−0.0029 (13)
C9	0.0205 (8)	0.0202 (8)	0.0173 (7)	−0.0016 (6)	−0.0003 (6)	−0.0012 (6)
C10	0.0286 (9)	0.0232 (9)	0.0189 (8)	−0.0089 (7)	0.0012 (7)	0.0012 (6)
C11	0.0208 (8)	0.0274 (9)	0.0252 (9)	−0.0083 (7)	0.0013 (6)	−0.0056 (7)
C12	0.0197 (8)	0.0246 (9)	0.0242 (8)	−0.0015 (6)	−0.0067 (6)	−0.0025 (7)
C13	0.0225 (8)	0.0224 (9)	0.0234 (9)	−0.0034 (6)	−0.0059 (7)	0.0036 (6)
C14	0.0166 (7)	0.0208 (8)	0.0183 (8)	−0.0017 (6)	−0.0020 (6)	−0.0001 (6)
C15	0.0175 (7)	0.0197 (8)	0.0170 (7)	−0.0016 (6)	−0.0004 (6)	0.0023 (6)
C16	0.0144 (7)	0.0174 (8)	0.0159 (7)	−0.0027 (5)	−0.0014 (5)	0.0000 (6)
C17	0.0222 (8)	0.0188 (8)	0.0165 (7)	−0.0009 (6)	0.0000 (6)	−0.0010 (6)
C18	0.0165 (7)	0.0183 (8)	0.0191 (7)	−0.0018 (6)	−0.0008 (6)	0.0004 (6)
C19	0.0213 (8)	0.0197 (8)	0.0191 (8)	0.0003 (6)	−0.0011 (6)	0.0025 (6)

Sn1—O1	2.118 (1)	C6—C7	1.506 (3)
Sn1—O2	2.106 (1)	C6—H6A	0.9900
Sn1—C1	2.136 (2)	C6—H6B	0.9900
Sn1—C5	2.136 (2)	C7—C8	1.513 (3)
Sn1—N1	2.215 (1)	C7—H7A	0.9900
Cl1—C12	1.7476 (17)	C7—H7B	0.9900
N1—C15	1.292 (2)	C8—H8A	0.9800
N1—C16	1.4852 (19)	C8—H8B	0.9800
O1—C9	1.314 (2)	C8—H8C	0.9800
O2—C17	1.4091 (19)	C9—C10	1.413 (2)
O3—C18	1.4224 (18)	C9—C14	1.415 (2)
O3—H3O	0.831 (10)	C10—C11	1.378 (2)
O4—C19	1.419 (2)	C10—H10	0.9500
O4—H4O	0.840 (10)	C11—C12	1.394 (3)
C1—C2	1.526 (3)	C11—H11	0.9500
C1—H1A	0.9900	C12—C13	1.370 (2)
C1—H1B	0.9900	C13—C14	1.415 (2)
C2—C3	1.523 (3)	C13—H13	0.9500
C2—H2A	0.9900	C14—C15	1.445 (2)
C2—H2B	0.9900	C15—H15	0.9500
C3—C4	1.504 (3)	C16—C19	1.534 (2)
C3—H3A	0.9900	C16—C18	1.535 (2)
C3—H3B	0.9900	C16—C17	1.541 (2)
C4—H4A	0.9800	C17—H17A	0.9900
C4—H4B	0.9800	C17—H17B	0.9900
C4—H4C	0.9800	C18—H18A	0.9900
C5—C6	1.519 (3)	C18—H18B	0.9900
C5—H5A	0.9900	C19—H19B	0.9900
C5—H5B	0.9900	C19—H19A	0.9900
O2—Sn1—O1	156.02 (5)	C8—C7—H7A	108.5
O2—Sn1—C1	91.30 (6)	C6—C7—H7B	108.5
O1—Sn1—C1	91.98 (6)	C8—C7—H7B	108.5
O2—Sn1—C5	98.13 (6)	H7A—C7—H7B	107.5
O1—Sn1—C5	97.80 (6)	C7—C8—H8A	109.5
C1—Sn1—C5	130.26 (8)	C7—C8—H8B	109.5
O2—Sn1—N1	76.31 (5)	H8A—C8—H8B	109.5
O1—Sn1—N1	81.67 (5)	C7—C8—H8C	109.5
C1—Sn1—N1	121.08 (6)	H8A—C8—H8C	109.5
C5—Sn1—N1	108.59 (7)	H8B—C8—H8C	109.5
C15—N1—C16	120.89 (13)	O1—C9—C10	119.58 (15)
C15—N1—Sn1	125.01 (11)	O1—C9—C14	122.82 (14)
C16—N1—Sn1	113.79 (9)	C10—C9—C14	117.57 (14)
C9—O1—Sn1	126.37 (11)	C11—C10—C9	121.35 (16)
C17—O2—Sn1	115.22 (9)	C11—C10—H10	119.3
C18—O3—H3O	110.1 (17)	C9—C10—H10	119.3
C19—O4—H4O	110.5 (16)	C10—C11—C12	120.03 (15)
C2—C1—Sn1	117.49 (12)	C10—C11—H11	120.0
C2—C1—H1A	107.9	C12—C11—H11	120.0
Sn1—C1—H1A	107.9	C13—C12—C11	120.74 (15)
C2—C1—H1B	107.9	C13—C12—Cl1	119.85 (14)
Sn1—C1—H1B	107.9	C11—C12—Cl1	119.40 (13)
H1A—C1—H1B	107.2	C12—C13—C14	119.79 (16)
C3—C2—C1	114.53 (17)	C12—C13—H13	120.1
C3—C2—H2A	108.6	C14—C13—H13	120.1
C1—C2—H2A	108.6	C9—C14—C13	120.36 (15)
C3—C2—H2B	108.6	C9—C14—C15	123.44 (14)
C1—C2—H2B	108.6	C13—C14—C15	116.18 (15)
H2A—C2—H2B	107.6	N1—C15—C14	126.46 (15)
C4—C3—C2	113.76 (19)	N1—C15—H15	116.8
C4—C3—H3A	108.8	C14—C15—H15	116.8
C2—C3—H3A	108.8	N1—C16—C19	115.43 (12)
C4—C3—H3B	108.8	N1—C16—C18	105.80 (12)
C2—C3—H3B	108.8	C19—C16—C18	112.02 (13)
H3A—C3—H3B	107.7	N1—C16—C17	105.13 (12)
C3—C4—H4A	109.5	C19—C16—C17	107.40 (13)
C3—C4—H4B	109.5	C18—C16—C17	110.87 (12)
H4A—C4—H4B	109.5	O2—C17—C16	111.11 (13)
C3—C4—H4C	109.5	O2—C17—H17A	109.4
H4A—C4—H4C	109.5	C16—C17—H17A	109.4
H4B—C4—H4C	109.5	O2—C17—H17B	109.4
C6—C5—Sn1	117.23 (14)	C16—C17—H17B	109.4
C6—C5—H5A	108.0	H17A—C17—H17B	108.0
Sn1—C5—H5A	108.0	O3—C18—C16	111.62 (13)
C6—C5—H5B	108.0	O3—C18—H18A	109.3
Sn1—C5—H5B	108.0	C16—C18—H18A	109.3
H5A—C5—H5B	107.2	O3—C18—H18B	109.3
C7—C6—C5	114.67 (17)	C16—C18—H18B	109.3
C7—C6—H6A	108.6	H18A—C18—H18B	108.0
C5—C6—H6A	108.6	O4—C19—C16	116.64 (14)
C7—C6—H6B	108.6	O4—C19—H19B	108.1
C5—C6—H6B	108.6	C16—C19—H19B	108.1
H6A—C6—H6B	107.6	O4—C19—H19A	108.1
C6—C7—C8	114.9 (2)	C16—C19—H19A	108.1
C6—C7—H7A	108.5	H19B—C19—H19A	107.3
O2—Sn1—N1—C15	−163.22 (14)	C9—C10—C11—C12	3.4 (3)
O1—Sn1—N1—C15	26.37 (13)	C10—C11—C12—C13	0.1 (3)
C1—Sn1—N1—C15	113.65 (14)	C10—C11—C12—Cl1	179.67 (14)
C5—Sn1—N1—C15	−69.11 (15)	C11—C12—C13—C14	−3.2 (3)
O2—Sn1—N1—C16	10.39 (10)	Cl1—C12—C13—C14	177.18 (14)
O1—Sn1—N1—C16	−160.03 (11)	O1—C9—C14—C13	178.46 (16)
C1—Sn1—N1—C16	−72.75 (12)	C10—C9—C14—C13	0.4 (2)
C5—Sn1—N1—C16	104.50 (11)	O1—C9—C14—C15	0.4 (3)
O2—Sn1—O1—C9	−64.26 (19)	C10—C9—C14—C15	−177.68 (16)
C1—Sn1—O1—C9	−161.94 (14)	C12—C13—C14—C9	3.0 (3)
C5—Sn1—O1—C9	66.95 (14)	C12—C13—C14—C15	−178.85 (16)
N1—Sn1—O1—C9	−40.81 (13)	C16—N1—C15—C14	179.74 (15)
O1—Sn1—O2—C17	41.07 (18)	Sn1—N1—C15—C14	−7.1 (2)
C1—Sn1—O2—C17	138.89 (12)	C9—C14—C15—N1	−14.7 (3)
C5—Sn1—O2—C17	−90.09 (12)	C13—C14—C15—N1	167.15 (17)
N1—Sn1—O2—C17	17.16 (10)	C15—N1—C16—C19	23.6 (2)
O2—Sn1—C1—C2	−179.95 (15)	Sn1—N1—C16—C19	−150.32 (11)
O1—Sn1—C1—C2	−23.71 (15)	C15—N1—C16—C18	−100.89 (16)
C5—Sn1—C1—C2	78.25 (18)	Sn1—N1—C16—C18	85.21 (12)
N1—Sn1—C1—C2	−105.17 (15)	C15—N1—C16—C17	141.72 (15)
Sn1—C1—C2—C3	−62.2 (2)	Sn1—N1—C16—C17	−32.18 (14)
C1—C2—C3—C4	−61.8 (3)	Sn1—O2—C17—C16	−41.23 (15)
O2—Sn1—C5—C6	−176.69 (16)	N1—C16—C17—O2	46.68 (16)
O1—Sn1—C5—C6	21.30 (17)	C19—C16—C17—O2	170.11 (12)
C1—Sn1—C5—C6	−78.01 (19)	C18—C16—C17—O2	−67.21 (16)
N1—Sn1—C5—C6	105.09 (17)	N1—C16—C18—O3	−178.13 (12)
Sn1—C5—C6—C7	−172.58 (17)	C19—C16—C18—O3	55.30 (17)
C5—C6—C7—C8	−175.3 (2)	C17—C16—C18—O3	−64.66 (16)
Sn1—O1—C9—C10	−146.41 (13)	N1—C16—C19—O4	−64.69 (18)
Sn1—O1—C9—C14	35.5 (2)	C18—C16—C19—O4	56.47 (18)
O1—C9—C10—C11	178.29 (16)	C17—C16—C19—O4	178.44 (13)
C14—C9—C10—C11	−3.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2i	0.83 (1)	1.79 (1)	2.612 (2)	172 (3)
O4—H4o···O3ii	0.84 (1)	1.94 (1)	2.739 (2)	160 (2)

Sn1—O1	2.118 (1)
Sn1—O2	2.106 (1)
Sn1—C1	2.136 (2)
Sn1—C5	2.136 (2)
Sn1—N1	2.215 (1)

C1—Sn1—C5

130.26 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O2i	0.83 (1)	1.79 (1)	2.612 (2)	172 (3)
O4—H4o⋯O3ii	0.84 (1)	1.94 (1)	2.739 (2)	160 (2)

Symmetry codes: (i) ; (ii) .