[3-(Dimethyl-amino)benzoato]triphenyl-tin(IV).

In the title compound, [Sn(C(6)H(5))(3)(C(9)H(10)NO(2))], the Sn atom is coordinated by three phenyl groups and a carboxyl-ate anion in a distorted tetra-hedral geometry. An intra-molecular C-H⋯O inter-action forms an S(7) ring motif. The dihedral angles between the benzoate group and the other three phenyl rings are 76.94 (8), 66.82 (8) and 42.34 (9)°. The crystal structure is further stabilized by inter-molecular C-H⋯π inter-actions.

Related literature

For hydrogen-bond motifs, see Bernstein et al. (1995 ▶). For values of bond lengths, see Allen et al. (1987 ▶). For related literature on n class="Chemical">triorganotin(IV) complexes see, for example: Willem et al. (1997 ▶); Novelli et al. (1999 ▶); Gielen et al. (2000 ▶); Tian et al. (2005 ▶); Baul et al. (2001 ▶); Win et al. (2006 ▶, 2007a ▶,b ▶); Yeap & Teoh (2003 ▶).

Experimental

Crystal data

[Sn(n class="CellLine">C6H5)3(C9H10NO2)]

M = 514.17

Triclinic,

a = 9.1140 (2) Å

b = 10.0027 (2) Å

c = 14.5066 (4) Å

α = 100.925 (1)°

β = 103.106 (1)°

γ = 110.778 (1)°

V = 1150.13 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.13 mm−1

T = 100.0 (1) K

0.46 × 0.42 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.623, T max = 0.830

18268 measured reflections

5259 independent reflections

5141 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.049

S = 1.08

5259 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: n class="Gene">APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036337/kp2195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036337/kp2195Isup2.hkl

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

[Sn(C6H5)3(C9H10NO2)]	Z = 2
Mr = 514.17	F000 = 520
Triclinic, P1	Dx = 1.485 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.1140 (2) Å	Cell parameters from 9986 reflections
b = 10.0027 (2) Å	θ = 2.5–31.2º
c = 14.5066 (4) Å	µ = 1.13 mm−1
α = 100.925 (1)º	T = 100.0 (1) K
β = 103.106 (1)º	Block, colourless
γ = 110.778 (1)º	0.46 × 0.42 × 0.17 mm
V = 1150.13 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5259 independent reflections
Radiation source: fine-focus sealed tube	5141 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 100.0(1) K	θmax = 27.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.623, Tmax = 0.830	k = −12→12
18268 measured reflections	l = −18→18

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)] = 0.017	H-atom parameters constrained
wR(F2) = 0.049	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.592P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
5259 reflections	Δρmax = 0.53 e Å−3
282 parameters	Δρmin = −0.56 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.091614 (11)	0.100499 (9)	0.838745 (6)	0.01429 (4)
O1	0.18084 (14)	0.11930 (12)	0.72088 (8)	0.0197 (2)
O2	0.11484 (14)	0.31350 (12)	0.73771 (8)	0.0204 (2)
N1	0.22892 (18)	0.51484 (16)	0.45101 (10)	0.0254 (3)
C1	0.22847 (18)	0.28442 (15)	0.96940 (10)	0.0159 (3)
C2	0.14887 (19)	0.36829 (17)	1.00604 (11)	0.0207 (3)
H2A	0.0400	0.3462	0.9710	0.025*
C3	0.2303 (2)	0.48439 (18)	1.09426 (12)	0.0244 (3)
H3A	0.1762	0.5399	1.1177	0.029*
C4	0.3920 (2)	0.51738 (17)	1.14722 (12)	0.0229 (3)
H4A	0.4465	0.5948	1.2064	0.028*
C5	0.4729 (2)	0.43461 (18)	1.11195 (12)	0.0232 (3)
H5A	0.5816	0.4570	1.1474	0.028*
C6	0.39153 (19)	0.31856 (17)	1.02389 (12)	0.0205 (3)
H6A	0.4459	0.2631	1.0010	0.025*
C7	−0.16663 (18)	0.04727 (16)	0.79258 (10)	0.0158 (3)
C8	−0.23183 (19)	0.14256 (16)	0.75791 (11)	0.0194 (3)
H8A	−0.1615	0.2315	0.7516	0.023*
C9	−0.4012 (2)	0.10510 (18)	0.73291 (12)	0.0233 (3)
H9A	−0.4435	0.1683	0.7089	0.028*
C10	−0.5073 (2)	−0.02620 (19)	0.74368 (12)	0.0240 (3)
H10A	−0.6201	−0.0501	0.7280	0.029*
C11	−0.4443 (2)	−0.12170 (18)	0.77797 (12)	0.0230 (3)
H11A	−0.5151	−0.2100	0.7849	0.028*
C12	−0.27509 (19)	−0.08543 (17)	0.80205 (11)	0.0188 (3)
H12A	−0.2338	−0.1501	0.8247	0.023*
C13	0.13625 (18)	−0.08981 (16)	0.85493 (11)	0.0164 (3)
C14	0.2177 (2)	−0.09087 (18)	0.94868 (12)	0.0215 (3)
H14A	0.2560	−0.0066	1.0028	0.026*
C15	0.2422 (2)	−0.21653 (19)	0.96204 (12)	0.0251 (3)
H15A	0.2965	−0.2160	1.0248	0.030*
C16	0.1856 (2)	−0.34238 (18)	0.88169 (13)	0.0245 (3)
H16A	0.1999	−0.4271	0.8907	0.029*
C17	0.1073 (2)	−0.34218 (17)	0.78765 (13)	0.0225 (3)
H17A	0.0713	−0.4260	0.7336	0.027*
C18	0.08268 (18)	−0.21649 (17)	0.77429 (11)	0.0193 (3)
H18A	0.0302	−0.2169	0.7112	0.023*
C19	0.16464 (18)	0.23129 (16)	0.69218 (11)	0.0168 (3)
C20	0.20934 (18)	0.25094 (16)	0.60128 (10)	0.0172 (3)
C21	0.20685 (18)	0.37521 (16)	0.57167 (11)	0.0184 (3)
H21A	0.1814	0.4443	0.6098	0.022*
C22	0.24224 (19)	0.39733 (17)	0.48506 (11)	0.0199 (3)
C23	0.2867 (2)	0.29256 (19)	0.43204 (11)	0.0239 (3)
H23A	0.3153	0.3064	0.3758	0.029*
C24	0.2888 (2)	0.16944 (19)	0.46203 (12)	0.0246 (3)
H24A	0.3171	0.1014	0.4251	0.030*
C25	0.24929 (19)	0.14608 (17)	0.54641 (11)	0.0207 (3)
H25A	0.2494	0.0627	0.5659	0.025*
C26	0.2998 (2)	0.5495 (2)	0.37333 (13)	0.0306 (4)
H26A	0.2477	0.4636	0.3157	0.046*
H26B	0.4166	0.5755	0.3964	0.046*
H26C	0.2817	0.6321	0.3568	0.046*
C27	0.2286 (2)	0.64104 (19)	0.52007 (14)	0.0318 (4)
H27A	0.1372	0.6063	0.5449	0.048*
H27B	0.2177	0.7127	0.4865	0.048*
H27C	0.3305	0.6873	0.5743	0.048*

	U11	U22	U33	U12	U13	U23
Sn1	0.01477 (6)	0.01395 (6)	0.01457 (6)	0.00679 (4)	0.00447 (4)	0.00385 (4)
O1	0.0237 (5)	0.0211 (5)	0.0189 (5)	0.0116 (4)	0.0093 (4)	0.0091 (4)
O2	0.0243 (6)	0.0207 (5)	0.0194 (5)	0.0105 (4)	0.0108 (4)	0.0065 (4)
N1	0.0309 (7)	0.0256 (7)	0.0197 (6)	0.0100 (6)	0.0072 (6)	0.0110 (5)
C1	0.0177 (7)	0.0146 (6)	0.0149 (6)	0.0058 (5)	0.0057 (5)	0.0047 (5)
C2	0.0187 (7)	0.0234 (7)	0.0200 (7)	0.0105 (6)	0.0043 (6)	0.0057 (6)
C3	0.0273 (8)	0.0245 (8)	0.0235 (8)	0.0143 (7)	0.0097 (7)	0.0029 (6)
C4	0.0250 (8)	0.0190 (7)	0.0189 (7)	0.0055 (6)	0.0057 (6)	0.0018 (6)
C5	0.0176 (7)	0.0235 (7)	0.0231 (8)	0.0060 (6)	0.0035 (6)	0.0042 (6)
C6	0.0180 (7)	0.0206 (7)	0.0231 (7)	0.0093 (6)	0.0067 (6)	0.0041 (6)
C7	0.0155 (6)	0.0180 (6)	0.0125 (6)	0.0076 (5)	0.0041 (5)	0.0005 (5)
C8	0.0193 (7)	0.0170 (6)	0.0205 (7)	0.0079 (6)	0.0059 (6)	0.0028 (5)
C9	0.0210 (7)	0.0223 (7)	0.0268 (8)	0.0122 (6)	0.0050 (6)	0.0045 (6)
C10	0.0162 (7)	0.0289 (8)	0.0228 (8)	0.0082 (6)	0.0055 (6)	0.0023 (6)
C11	0.0200 (7)	0.0239 (7)	0.0205 (7)	0.0044 (6)	0.0067 (6)	0.0054 (6)
C12	0.0203 (7)	0.0198 (7)	0.0149 (7)	0.0077 (6)	0.0045 (6)	0.0042 (5)
C13	0.0151 (6)	0.0169 (6)	0.0198 (7)	0.0076 (5)	0.0072 (5)	0.0072 (5)
C14	0.0257 (8)	0.0234 (7)	0.0180 (7)	0.0120 (6)	0.0084 (6)	0.0064 (6)
C15	0.0289 (8)	0.0341 (9)	0.0236 (8)	0.0196 (7)	0.0119 (7)	0.0163 (7)
C16	0.0256 (8)	0.0245 (8)	0.0366 (9)	0.0162 (6)	0.0178 (7)	0.0167 (7)
C17	0.0217 (7)	0.0175 (7)	0.0296 (8)	0.0088 (6)	0.0115 (6)	0.0047 (6)
C18	0.0175 (7)	0.0195 (7)	0.0192 (7)	0.0073 (6)	0.0045 (6)	0.0050 (6)
C19	0.0147 (6)	0.0174 (6)	0.0152 (6)	0.0048 (5)	0.0031 (5)	0.0041 (5)
C20	0.0161 (7)	0.0199 (7)	0.0135 (6)	0.0063 (5)	0.0035 (5)	0.0041 (5)
C21	0.0186 (7)	0.0191 (7)	0.0158 (7)	0.0075 (5)	0.0044 (5)	0.0038 (5)
C22	0.0183 (7)	0.0223 (7)	0.0146 (7)	0.0053 (6)	0.0022 (5)	0.0055 (6)
C23	0.0256 (8)	0.0325 (8)	0.0127 (7)	0.0114 (7)	0.0068 (6)	0.0056 (6)
C24	0.0280 (8)	0.0300 (8)	0.0156 (7)	0.0150 (7)	0.0065 (6)	0.0009 (6)
C25	0.0228 (7)	0.0211 (7)	0.0170 (7)	0.0101 (6)	0.0043 (6)	0.0035 (6)
C26	0.0266 (8)	0.0360 (9)	0.0241 (8)	0.0052 (7)	0.0054 (7)	0.0164 (7)
C27	0.0408 (10)	0.0243 (8)	0.0311 (9)	0.0139 (7)	0.0091 (8)	0.0125 (7)

Sn1—O1	2.0649 (11)	C12—H12A	0.9300
Sn1—C1	2.1239 (15)	C13—C18	1.397 (2)
Sn1—C13	2.1260 (14)	C13—C14	1.398 (2)
Sn1—C7	2.1290 (14)	C14—C15	1.393 (2)
O1—C19	1.3101 (17)	C14—H14A	0.9300
O2—C19	1.2303 (19)	C15—C16	1.385 (2)
N1—C22	1.391 (2)	C15—H15A	0.9300
N1—C27	1.457 (2)	C16—C17	1.389 (2)
N1—C26	1.458 (2)	C16—H16A	0.9300
C1—C2	1.397 (2)	C17—C18	1.393 (2)
C1—C6	1.398 (2)	C17—H17A	0.9300
C2—C3	1.390 (2)	C18—H18A	0.9300
C2—H2A	0.9300	C19—C20	1.493 (2)
C3—C4	1.384 (2)	C20—C21	1.396 (2)
C3—H3A	0.9300	C20—C25	1.397 (2)
C4—C5	1.391 (2)	C21—C22	1.404 (2)
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.388 (2)	C22—C23	1.411 (2)
C5—H5A	0.9300	C23—C24	1.386 (2)
C6—H6A	0.9300	C23—H23A	0.9300
C7—C12	1.399 (2)	C24—C25	1.390 (2)
C7—C8	1.401 (2)	C24—H24A	0.9300
C8—C9	1.393 (2)	C25—H25A	0.9300
C8—H8A	0.9300	C26—H26A	0.9600
C9—C10	1.389 (2)	C26—H26B	0.9600
C9—H9A	0.9300	C26—H26C	0.9600
C10—C11	1.389 (2)	C27—H27A	0.9600
C10—H10A	0.9300	C27—H27B	0.9600
C11—C12	1.394 (2)	C27—H27C	0.9600
C11—H11A	0.9300
O1—Sn1—C1	114.69 (5)	C15—C14—C13	120.83 (15)
O1—Sn1—C13	95.46 (5)	C15—C14—H14A	119.6
C1—Sn1—C13	110.92 (6)	C13—C14—H14A	119.6
O1—Sn1—C7	109.89 (5)	C16—C15—C14	119.87 (15)
C1—Sn1—C7	113.28 (6)	C16—C15—H15A	120.1
C13—Sn1—C7	111.31 (5)	C14—C15—H15A	120.1
C19—O1—Sn1	109.13 (9)	C15—C16—C17	120.07 (14)
C22—N1—C27	118.52 (13)	C15—C16—H16A	120.0
C22—N1—C26	118.12 (15)	C17—C16—H16A	120.0
C27—N1—C26	115.85 (14)	C16—C17—C18	120.06 (15)
C2—C1—C6	118.61 (14)	C16—C17—H17A	120.0
C2—C1—Sn1	118.67 (11)	C18—C17—H17A	120.0
C6—C1—Sn1	122.57 (11)	C17—C18—C13	120.51 (14)
C3—C2—C1	120.82 (14)	C17—C18—H18A	119.7
C3—C2—H2A	119.6	C13—C18—H18A	119.7
C1—C2—H2A	119.6	O2—C19—O1	121.43 (13)
C4—C3—C2	119.94 (15)	O2—C19—C20	122.89 (13)
C4—C3—H3A	120.0	O1—C19—C20	115.68 (13)
C2—C3—H3A	120.0	C21—C20—C25	121.04 (14)
C3—C4—C5	119.97 (15)	C21—C20—C19	118.15 (13)
C3—C4—H4A	120.0	C25—C20—C19	120.80 (13)
C5—C4—H4A	120.0	C20—C21—C22	120.90 (14)
C6—C5—C4	120.12 (15)	C20—C21—H21A	119.6
C6—C5—H5A	119.9	C22—C21—H21A	119.6
C4—C5—H5A	119.9	N1—C22—C21	121.46 (15)
C5—C6—C1	120.54 (14)	N1—C22—C23	121.24 (14)
C5—C6—H6A	119.7	C21—C22—C23	117.27 (14)
C1—C6—H6A	119.7	C24—C23—C22	121.36 (14)
C12—C7—C8	118.59 (13)	C24—C23—H23A	119.3
C12—C7—Sn1	118.36 (10)	C22—C23—H23A	119.3
C8—C7—Sn1	122.97 (11)	C23—C24—C25	121.01 (15)
C9—C8—C7	120.51 (14)	C23—C24—H24A	119.5
C9—C8—H8A	119.7	C25—C24—H24A	119.5
C7—C8—H8A	119.7	C24—C25—C20	118.36 (14)
C10—C9—C8	120.31 (15)	C24—C25—H25A	120.8
C10—C9—H9A	119.8	C20—C25—H25A	120.8
C8—C9—H9A	119.8	N1—C26—H26A	109.5
C9—C10—C11	119.76 (15)	N1—C26—H26B	109.5
C9—C10—H10A	120.1	H26A—C26—H26B	109.5
C11—C10—H10A	120.1	N1—C26—H26C	109.5
C10—C11—C12	120.11 (15)	H26A—C26—H26C	109.5
C10—C11—H11A	119.9	H26B—C26—H26C	109.5
C12—C11—H11A	119.9	N1—C27—H27A	109.5
C11—C12—C7	120.71 (14)	N1—C27—H27B	109.5
C11—C12—H12A	119.6	H27A—C27—H27B	109.5
C7—C12—H12A	119.6	N1—C27—H27C	109.5
C18—C13—C14	118.64 (13)	H27A—C27—H27C	109.5
C18—C13—Sn1	121.68 (11)	H27B—C27—H27C	109.5
C14—C13—Sn1	119.66 (11)
C1—Sn1—O1—C19	−65.43 (10)	C7—Sn1—C13—C18	63.64 (13)
C13—Sn1—O1—C19	178.55 (10)	O1—Sn1—C13—C14	131.33 (12)
C7—Sn1—O1—C19	63.54 (10)	C1—Sn1—C13—C14	12.27 (13)
O1—Sn1—C1—C2	118.11 (11)	C7—Sn1—C13—C14	−114.83 (12)
C13—Sn1—C1—C2	−135.17 (11)	C18—C13—C14—C15	−1.3 (2)
C7—Sn1—C1—C2	−9.16 (13)	Sn1—C13—C14—C15	177.23 (12)
O1—Sn1—C1—C6	−66.39 (13)	C13—C14—C15—C16	0.1 (2)
C13—Sn1—C1—C6	40.33 (13)	C14—C15—C16—C17	1.2 (2)
C7—Sn1—C1—C6	166.35 (11)	C15—C16—C17—C18	−1.3 (2)
C6—C1—C2—C3	0.7 (2)	C16—C17—C18—C13	0.0 (2)
Sn1—C1—C2—C3	176.37 (12)	C14—C13—C18—C17	1.3 (2)
C1—C2—C3—C4	−0.4 (2)	Sn1—C13—C18—C17	−177.23 (11)
C2—C3—C4—C5	0.2 (2)	Sn1—O1—C19—O2	5.06 (17)
C3—C4—C5—C6	−0.2 (2)	Sn1—O1—C19—C20	−174.58 (10)
C4—C5—C6—C1	0.5 (2)	O2—C19—C20—C21	5.3 (2)
C2—C1—C6—C5	−0.7 (2)	O1—C19—C20—C21	−175.11 (13)
Sn1—C1—C6—C5	−176.25 (11)	O2—C19—C20—C25	−173.49 (14)
O1—Sn1—C7—C12	120.58 (11)	O1—C19—C20—C25	6.1 (2)
C1—Sn1—C7—C12	−109.69 (11)	C25—C20—C21—C22	0.9 (2)
C13—Sn1—C7—C12	16.12 (13)	C19—C20—C21—C22	−177.86 (13)
O1—Sn1—C7—C8	−62.74 (13)	C27—N1—C22—C21	18.9 (2)
C1—Sn1—C7—C8	67.00 (13)	C26—N1—C22—C21	167.49 (15)
C13—Sn1—C7—C8	−167.20 (12)	C27—N1—C22—C23	−163.14 (16)
C12—C7—C8—C9	−0.4 (2)	C26—N1—C22—C23	−14.6 (2)
Sn1—C7—C8—C9	−177.08 (12)	C20—C21—C22—N1	175.44 (14)
C7—C8—C9—C10	1.1 (2)	C20—C21—C22—C23	−2.5 (2)
C8—C9—C10—C11	−1.1 (2)	N1—C22—C23—C24	−175.42 (15)
C9—C10—C11—C12	0.4 (2)	C21—C22—C23—C24	2.6 (2)
C10—C11—C12—C7	0.3 (2)	C22—C23—C24—C25	−0.9 (3)
C8—C7—C12—C11	−0.3 (2)	C23—C24—C25—C20	−0.8 (2)
Sn1—C7—C12—C11	176.53 (11)	C21—C20—C25—C24	0.9 (2)
O1—Sn1—C13—C18	−50.20 (12)	C19—C20—C25—C24	179.56 (14)
C1—Sn1—C13—C18	−169.26 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2	0.93	2.43	3.126 (2)	132
C24—H24A···Cg1i	0.93	2.88	3.6772 (19)	144
C26—H26B···Cg2ii	0.96	2.74	3.672 (2)	164

Table 1

Selected bond lengths (Å)

Sn1—O1	2.0649 (11)
Sn1—C1	2.1239 (15)
Sn1—C13	2.1260 (14)
Sn1—C7	2.1290 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2	0.93	2.43	3.126 (2)	132
C24—H24A⋯Cg1i	0.93	2.88	3.6772 (19)	144
C26—H26B⋯Cg2ii	0.96	2.74	3.672 (2)	164

Symmetry codes: (i) ; (ii) .