Chloridomethyl­phen­yl(quinoline-2-carboxyl­ato-κ2N,O)tin(IV)

Vafaee, M.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810027595

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m947

https://doi.org/10.1107/S1600536810027595

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Chloridomethylphenyl(quinoline-2-carboxylato-κ²N,O)tin(IV)

Maryam Vafaee,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 11 July 2010; accepted 12 July 2010; online 17 July 2010)

The Sn atom in the title compound, [Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)Cl], shows a distorted C₂SnNOCl trigonal-bipyramidal coordination; the apical sites are occupied by the N and Cl atoms.

Related literature

For chloridodimethyl(quinoline-2-carboxylato)tin(IV), see: Wang et al. (2007 ).

Experimental

Crystal data

[Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)Cl]
M_r = 418.43
Monoclinic, P 2₁ /n
a = 10.6942 (5) Å
b = 13.1463 (6) Å
c = 11.2733 (5) Å
β = 93.689 (1)°
V = 1581.6 (1) Å³
Z = 4
Mo Kα radiation
μ = 1.79 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.616, T_max = 0.841
14187 measured reflections
3613 independent reflections
3433 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.40
3613 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—C1	2.117 (3)
Sn1—C2	2.122 (2)
Sn1—N1	2.369 (2)
Sn1—O1	2.062 (2)
Sn1—Cl1	2.4414 (7)

C1—Sn1—C2	138.58 (9)

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: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810027595/bt5296sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027595/bt5296Isup2.hkl

checkCIF report

Comment top

The tin atom in chlorodimethyl(quinoline-2-carboxylate)tin shows cis-C₂SnNOCl trigonal bipyramidal coordination, with the C₂Sn skeleton being bent at 131.8 (2) ° (Wang et al., 2007). Replacing one of the methyl groups by a bulkier phenyl group in the title analog (Scheme I, Fig. 1) leads to only a marginal opening of the angle 138.6 (1) °; the trans angle is also marginally increased.

Related literature top

For chloridodimethyl(quinoline-2-carboxylato)tin, see: Wang et al. (2007).

Experimental top

Sodium quinoline-2-carboxylate was synthesized by reacting sodium hydroxide and quinoline-2-carboxylic acid in toluene in a Dean-Start apparatus. The compound (0.20 g, 1 mmol) was then stirred with methylphenyltin dichloride (0.35 g, 1 mmol) in toluene; no heat was applied. The precipitate that formed was recrystallized from methanol.

Structure description top

For chloridodimethyl(quinoline-2-carboxylato)tin, see: Wang et al. (2007).

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: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of SnCl(CH₃)(C₆H₅)(C₁₀H₆NO₂) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Chloridomethylphenyl(quinoline-2-carboxylato-κ²N,O)tin(IV) top

Crystal data top

[Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)Cl]	F(000) = 824
M_r = 418.43	D_x = 1.757 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9943 reflections
a = 10.6942 (5) Å	θ = 2.4–28.3°
b = 13.1463 (6) Å	µ = 1.79 mm⁻¹
c = 11.2733 (5) Å	T = 100 K
β = 93.689 (1)°	Prism, colorless
V = 1581.6 (1) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3613 independent reflections
Radiation source: fine-focus sealed tube	3433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.616, T_max = 0.841	k = −17→17
14187 measured reflections	l = −14→14

Refinement top

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0523P)² + 0.1663P] where P = (F_o² + 2F_c²)/3
S = 1.40	(Δ/σ)_max = 0.001
3613 reflections	Δρ_max = 1.74 e Å⁻³
201 parameters	Δρ_min = −0.94 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0280 (15)

Crystal data top

[Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)Cl]	V = 1581.6 (1) Å³
M_r = 418.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.6942 (5) Å	µ = 1.79 mm⁻¹
b = 13.1463 (6) Å	T = 100 K
c = 11.2733 (5) Å	0.30 × 0.20 × 0.10 mm
β = 93.689 (1)°

Data collection top

Bruker SMART APEX diffractometer	3613 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3433 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.841	R_int = 0.039
14187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.40	Δρ_max = 1.74 e Å⁻³
3613 reflections	Δρ_min = −0.94 e Å⁻³
201 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.813061 (14)	0.776948 (11)	0.733408 (14)	0.01396 (11)
Cl1	1.02998 (6)	0.75394 (6)	0.68330 (7)	0.02452 (16)
O1	0.77940 (15)	0.62981 (12)	0.67664 (15)	0.0176 (3)
O2	0.64876 (17)	0.49885 (13)	0.64587 (16)	0.0217 (4)
C1	0.8465 (3)	0.77556 (17)	0.9205 (3)	0.0226 (6)
H1A	0.7742	0.8046	0.9575	0.034*
H1B	0.9213	0.8160	0.9428	0.034*
H1C	0.8596	0.7054	0.9479	0.034*
C2	0.7644 (2)	0.88296 (16)	0.59620 (19)	0.0139 (4)
C3	0.6502 (2)	0.87698 (17)	0.52921 (19)	0.0161 (4)
H3	0.5931	0.8236	0.5435	0.019*
C4	0.6195 (2)	0.94912 (19)	0.4413 (2)	0.0193 (5)
H4	0.5427	0.9438	0.3945	0.023*
C5	0.7010 (2)	1.02855 (18)	0.4224 (2)	0.0203 (5)
H5	0.6785	1.0791	0.3647	0.024*
C6	0.8157 (2)	1.03451 (17)	0.4877 (2)	0.0197 (5)
H6	0.8719	1.0887	0.4742	0.024*
C7	0.8479 (2)	0.96066 (17)	0.5731 (2)	0.0167 (4)
H7	0.9274	0.9634	0.6158	0.020*
C8	0.6698 (2)	0.58635 (18)	0.6779 (2)	0.0163 (4)
C9	0.5661 (2)	0.65049 (17)	0.72434 (19)	0.0146 (4)
C10	0.4453 (2)	0.61082 (18)	0.7341 (2)	0.0178 (4)
H10	0.4255	0.5435	0.7089	0.021*
C11	0.3567 (2)	0.67171 (19)	0.7810 (2)	0.0187 (5)
H11	0.2747	0.6462	0.7898	0.022*
C12	0.3874 (3)	0.77218 (16)	0.8162 (2)	0.0158 (5)
C13	0.3008 (2)	0.83899 (19)	0.8662 (2)	0.0193 (5)
H13	0.2194	0.8153	0.8813	0.023*
C14	0.3339 (2)	0.9378 (2)	0.8929 (2)	0.0207 (5)
H14	0.2759	0.9819	0.9271	0.025*
C15	0.4546 (2)	0.97368 (18)	0.86940 (19)	0.0186 (5)
H15	0.4754	1.0429	0.8845	0.022*
C16	0.5418 (2)	0.91036 (18)	0.82531 (19)	0.0172 (4)
H16	0.6234	0.9351	0.8126	0.021*
C17	0.5105 (2)	0.80846 (18)	0.79870 (19)	0.0140 (4)
N1	0.5977 (2)	0.74461 (18)	0.75477 (18)	0.0139 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01151 (15)	0.01373 (15)	0.01635 (15)	−0.00098 (4)	−0.00142 (8)	0.00397 (4)
Cl1	0.0122 (3)	0.0219 (3)	0.0395 (4)	0.0004 (3)	0.0017 (2)	0.0078 (3)
O1	0.0146 (8)	0.0141 (8)	0.0244 (9)	−0.0003 (6)	0.0028 (6)	−0.0009 (6)
O2	0.0208 (9)	0.0156 (8)	0.0286 (9)	−0.0014 (7)	0.0008 (7)	−0.0046 (7)
C1	0.0274 (15)	0.0217 (13)	0.0179 (13)	−0.0011 (9)	−0.0052 (11)	0.0035 (8)
C2	0.0152 (10)	0.0134 (10)	0.0133 (9)	0.0019 (8)	0.0027 (8)	0.0011 (8)
C3	0.0148 (11)	0.0176 (11)	0.0162 (10)	0.0009 (8)	0.0020 (8)	−0.0006 (8)
C4	0.0192 (11)	0.0236 (12)	0.0152 (10)	0.0072 (9)	0.0004 (8)	−0.0009 (9)
C5	0.0302 (13)	0.0177 (12)	0.0134 (10)	0.0090 (10)	0.0054 (9)	0.0024 (8)
C6	0.0268 (12)	0.0135 (10)	0.0198 (11)	0.0006 (9)	0.0088 (9)	0.0020 (8)
C7	0.0179 (11)	0.0145 (10)	0.0178 (10)	−0.0005 (8)	0.0021 (8)	−0.0007 (8)
C8	0.0174 (11)	0.0164 (11)	0.0151 (10)	−0.0006 (8)	0.0011 (8)	0.0020 (8)
C9	0.0139 (11)	0.0154 (11)	0.0142 (10)	−0.0005 (8)	−0.0007 (8)	0.0022 (8)
C10	0.0166 (11)	0.0143 (10)	0.0223 (11)	−0.0033 (8)	−0.0002 (9)	0.0030 (8)
C11	0.0142 (11)	0.0196 (12)	0.0223 (11)	−0.0028 (9)	0.0013 (9)	0.0067 (9)
C12	0.0133 (12)	0.0207 (13)	0.0135 (11)	0.0010 (8)	0.0012 (9)	0.0060 (7)
C13	0.0170 (11)	0.0253 (12)	0.0157 (10)	0.0016 (9)	0.0022 (8)	0.0041 (8)
C14	0.0218 (12)	0.0257 (13)	0.0146 (10)	0.0059 (10)	0.0011 (9)	0.0002 (9)
C15	0.0245 (12)	0.0174 (11)	0.0135 (10)	0.0005 (9)	−0.0023 (9)	−0.0012 (8)
C16	0.0193 (11)	0.0176 (11)	0.0147 (10)	−0.0016 (8)	−0.0002 (8)	0.0017 (8)
C17	0.0144 (11)	0.0163 (11)	0.0113 (9)	−0.0004 (9)	0.0001 (8)	0.0029 (8)
N1	0.0136 (10)	0.0142 (9)	0.0139 (9)	−0.0009 (8)	0.0001 (7)	0.0025 (8)

Geometric parameters (Å, º) top

Sn1—C1	2.117 (3)	C7—H7	0.9500
Sn1—C2	2.122 (2)	C8—C9	1.513 (3)
Sn1—N1	2.369 (2)	C9—N1	1.322 (3)
Sn1—O1	2.062 (2)	C9—C10	1.404 (3)
Sn1—Cl1	2.4414 (7)	C10—C11	1.373 (3)
O1—C8	1.305 (3)	C10—H10	0.9500
O2—C8	1.222 (3)	C11—C12	1.412 (4)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C13	1.420 (3)
C1—H1C	0.9800	C12—C17	1.426 (3)
C2—C7	1.392 (3)	C13—C14	1.375 (4)
C2—C3	1.397 (3)	C13—H13	0.9500
C3—C4	1.395 (3)	C14—C15	1.415 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.385 (4)	C15—C16	1.367 (3)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.392 (4)	C16—C17	1.408 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.394 (3)	C17—N1	1.371 (3)
C6—H6	0.9500

O1—Sn1—C1	108.43 (8)	C6—C7—H7	119.8
O1—Sn1—C2	111.11 (7)	O2—C8—O1	123.9 (2)
C1—Sn1—C2	138.58 (9)	O2—C8—C9	120.1 (2)
O1—Sn1—N1	73.25 (7)	O1—C8—C9	116.0 (2)
C1—Sn1—N1	90.02 (10)	N1—C9—C10	123.3 (2)
C2—Sn1—N1	89.86 (8)	N1—C9—C8	115.5 (2)
O1—Sn1—Cl1	87.79 (5)	C10—C9—C8	121.2 (2)
C1—Sn1—Cl1	97.31 (9)	C11—C10—C9	118.4 (2)
C2—Sn1—Cl1	96.02 (6)	C11—C10—H10	120.8
N1—Sn1—Cl1	161.00 (7)	C9—C10—H10	120.8
C8—O1—Sn1	123.13 (14)	C10—C11—C12	120.0 (2)
Sn1—C1—H1A	109.5	C10—C11—H11	120.0
Sn1—C1—H1B	109.5	C12—C11—H11	120.0
H1A—C1—H1B	109.5	C11—C12—C13	123.0 (2)
Sn1—C1—H1C	109.5	C11—C12—C17	118.3 (2)
H1A—C1—H1C	109.5	C13—C12—C17	118.7 (2)
H1B—C1—H1C	109.5	C14—C13—C12	120.4 (2)
C7—C2—C3	119.3 (2)	C14—C13—H13	119.8
C7—C2—Sn1	119.21 (16)	C12—C13—H13	119.8
C3—C2—Sn1	121.48 (16)	C13—C14—C15	120.0 (2)
C4—C3—C2	120.2 (2)	C13—C14—H14	120.0
C4—C3—H3	119.9	C15—C14—H14	120.0
C2—C3—H3	119.9	C16—C15—C14	121.1 (2)
C5—C4—C3	120.0 (2)	C16—C15—H15	119.4
C5—C4—H4	120.0	C14—C15—H15	119.4
C3—C4—H4	120.0	C15—C16—C17	119.9 (2)
C4—C5—C6	120.2 (2)	C15—C16—H16	120.1
C4—C5—H5	119.9	C17—C16—H16	120.1
C6—C5—H5	119.9	N1—C17—C16	120.1 (2)
C5—C6—C7	119.7 (2)	N1—C17—C12	120.1 (2)
C5—C6—H6	120.1	C16—C17—C12	119.8 (2)
C7—C6—H6	120.1	C9—N1—C17	119.9 (2)
C2—C7—C6	120.5 (2)	C9—N1—Sn1	112.07 (16)
C2—C7—H7	119.8	C17—N1—Sn1	127.97 (17)

C1—Sn1—O1—C8	83.29 (19)	C10—C11—C12—C13	−179.5 (2)
C2—Sn1—O1—C8	−84.14 (18)	C10—C11—C12—C17	1.6 (4)
N1—Sn1—O1—C8	−0.97 (16)	C11—C12—C13—C14	−176.5 (2)
Cl1—Sn1—O1—C8	−179.74 (16)	C17—C12—C13—C14	2.4 (3)
O1—Sn1—C2—C7	−133.04 (16)	C12—C13—C14—C15	0.7 (3)
C1—Sn1—C2—C7	65.2 (2)	C13—C14—C15—C16	−3.0 (3)
N1—Sn1—C2—C7	155.02 (17)	C14—C15—C16—C17	2.2 (3)
Cl1—Sn1—C2—C7	−43.08 (17)	C15—C16—C17—N1	−179.8 (2)
O1—Sn1—C2—C3	47.46 (19)	C15—C16—C17—C12	1.0 (3)
C1—Sn1—C2—C3	−114.4 (2)	C11—C12—C17—N1	−3.5 (3)
N1—Sn1—C2—C3	−24.49 (18)	C13—C12—C17—N1	177.5 (2)
Cl1—Sn1—C2—C3	137.41 (17)	C11—C12—C17—C16	175.8 (2)
C7—C2—C3—C4	−1.0 (3)	C13—C12—C17—C16	−3.2 (3)
Sn1—C2—C3—C4	178.55 (16)	C10—C9—N1—C17	0.2 (3)
C2—C3—C4—C5	−1.7 (3)	C8—C9—N1—C17	−179.51 (19)
C3—C4—C5—C6	2.5 (3)	C10—C9—N1—Sn1	176.98 (17)
C4—C5—C6—C7	−0.5 (3)	C8—C9—N1—Sn1	−2.7 (2)
C3—C2—C7—C6	2.9 (3)	C16—C17—N1—C9	−176.6 (2)
Sn1—C2—C7—C6	−176.62 (17)	C12—C17—N1—C9	2.6 (3)
C5—C6—C7—C2	−2.2 (3)	C16—C17—N1—Sn1	7.2 (3)
Sn1—O1—C8—O2	−179.09 (17)	C12—C17—N1—Sn1	−173.62 (16)
Sn1—O1—C8—C9	−0.1 (3)	O1—Sn1—N1—C9	2.05 (15)
O2—C8—C9—N1	−178.9 (2)	C1—Sn1—N1—C9	−107.22 (17)
O1—C8—C9—N1	2.1 (3)	C2—Sn1—N1—C9	114.19 (16)
O2—C8—C9—C10	1.4 (3)	Cl1—Sn1—N1—C9	5.8 (3)
O1—C8—C9—C10	−177.6 (2)	O1—Sn1—N1—C17	178.5 (2)
N1—C9—C10—C11	−2.1 (3)	C1—Sn1—N1—C17	69.2 (2)
C8—C9—C10—C11	177.6 (2)	C2—Sn1—N1—C17	−69.4 (2)
C9—C10—C11—C12	1.1 (4)	Cl1—Sn1—N1—C17	−177.71 (13)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)(C₆H₅)(C₁₀H₆NO₂)Cl]
M_r	418.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.6942 (5), 13.1463 (6), 11.2733 (5)
β (°)	93.689 (1)
V (Å³)	1581.6 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.616, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	14187, 3613, 3433
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.40
No. of reflections	3613
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −0.94

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

Selected geometric parameters (Å, º) top

Sn1—C1	2.117 (3)	Sn1—O1	2.062 (2)
Sn1—C2	2.122 (2)	Sn1—Cl1	2.4414 (7)
Sn1—N1	2.369 (2)

C1—Sn1—C2	138.58 (9)

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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