Dibutyl­bis[3-(dimethyl­amino)benzoato]tin(IV)

The molecule of the title compound, [Sn(C₄H₉)₂(C₉H₁₀NO₂)₂], has twofold rotation symmetry. The geometry of the Sn atom is distorted tetra­hedral. The dimethyl­amine substituent is twisted slightly from the benzene ring. The mol­ecules are stabilized by weak inter­molecular C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.079
• Data-to-parameter ratio = 45.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Sn1    -   O2      ..      10.27 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.600     0.771
            Tmin(prime) and Tmax expected:      0.670     0.763
            RR(prime) =      0.886
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Dibutylbis[3-(dimethylamino)benzoato]tin(IV)

Crystal data

[Sn(C4H9)2(C9H10NO2)2]	F(000) = 1160
Mr = 561.27	Dx = 1.412 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8950 reflections
a = 15.2076 (6) Å	θ = 2.7–37.5°
b = 6.9231 (2) Å	µ = 1.00 mm^−1
c = 25.4477 (8) Å	T = 100 K
β = 99.734 (2)°	Block, colourless
V = 2640.66 (15) Å^3	0.39 × 0.36 × 0.27 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	6946 independent reflections
Radiation source: fine-focus sealed tube	6844 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm^-1	θmax = 37.5°, θmin = 2.7°
ω scans	h = −26→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.600, Tmax = 0.771	l = −43→40
45032 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.39	w = 1/[σ^2(Fo^2) + (0.0176P)^2 + 4.3428P] where P = (Fo^2 + 2Fc^2)/3
6946 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 1.36 e Å^−3
0 restraints	Δρmin = −1.14 e Å^−3

Special details

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

FT–IR (KBr, cm^-1): ν(COO)_as 1608, 1595, ν(COO)_s 1360, ν(O—Sn—O) 679, ν(Sn—C) 554, ν(Sn—O) 476; ¹H NMR (Solvent?, δ, p.p.m.): benzene H atoms 6.93–6.95 (2H, d, J = 7.9 Hz), 7.29–7.34 (2H, t, J = 8.0 Hz), 7.48–7.51 (4H, d, J = 8.5 Hz); N—(CH₃)₂ 3.01 (12H, s); butyl CH₃ 0.86–0.90 (6H, t, J = 7.3 Hz); CH₂ 1.34–1.44 (4H, hx, 7.2 Hz); CH₂ 1.69–1.84 (8H, m); ¹³C NMR (Solvent?, δ, p.p.m.): benzene C atoms 114.42, 117.40, 119.02, 129.36, 131.09, 150.86; N—(CH₃)₂ 41.02; butyl 13.98, 25.85, 26.82, 27.11; COO 177.25; ¹¹⁹Sn NMR (Solvent?, δ, p.p.m.): -156.40.

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 (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.0000	0.876787 (19)	0.2500	0.01675 (3)
O1	0.02778 (7)	1.10261 (16)	0.20103 (4)	0.02048 (18)
O2	0.04885 (8)	0.83265 (16)	0.15908 (4)	0.02163 (18)
N1	0.15016 (9)	1.0573 (2)	−0.01258 (5)	0.0246 (2)
C1	0.04861 (9)	1.0127 (2)	0.16007 (5)	0.0179 (2)
C2	0.07026 (9)	1.1333 (2)	0.11555 (5)	0.0187 (2)
C3	0.06248 (11)	1.3332 (2)	0.11719 (6)	0.0220 (2)
H3A	0.0457	1.3943	0.1465	0.026*
C4	0.08039 (12)	1.4393 (2)	0.07379 (7)	0.0261 (3)
H4A	0.0743	1.5730	0.0739	0.031*
C5	0.10723 (11)	1.3493 (2)	0.03038 (6)	0.0252 (3)
H5A	0.1182	1.4236	0.0017	0.030*
C6	0.11813 (9)	1.1481 (2)	0.02893 (5)	0.0200 (2)
C7	0.09726 (9)	1.0406 (2)	0.07229 (5)	0.0181 (2)
H7A	0.1016	0.9066	0.0720	0.022*
C8	0.12392 (10)	0.7559 (2)	0.28506 (6)	0.0206 (2)
H8A	0.1691	0.7950	0.2645	0.025*
H8B	0.1407	0.8079	0.3207	0.025*
C9	0.12301 (10)	0.5360 (2)	0.28836 (7)	0.0235 (3)
H9A	0.0742	0.4954	0.3059	0.028*
H9B	0.1126	0.4828	0.2526	0.028*
C10	0.21035 (10)	0.4561 (2)	0.31883 (7)	0.0249 (3)
H10A	0.2590	0.4975	0.3012	0.030*
H10B	0.2206	0.5100	0.3545	0.030*
C11	0.21139 (13)	0.2367 (3)	0.32274 (9)	0.0345 (4)
H11A	0.2678	0.1948	0.3422	0.052*
H11B	0.2026	0.1821	0.2876	0.052*
H11C	0.1644	0.1947	0.3410	0.052*
C12	0.13892 (11)	0.8490 (3)	−0.01853 (6)	0.0259 (3)
H12A	0.1709	0.7855	0.0124	0.039*
H12B	0.1617	0.8069	−0.0496	0.039*
H12C	0.0767	0.8172	−0.0224	0.039*
C13	0.15367 (12)	1.1675 (3)	−0.06104 (6)	0.0291 (3)
H13A	0.1887	1.2819	−0.0523	0.044*
H13B	0.0943	1.2031	−0.0773	0.044*
H13C	0.1803	1.0899	−0.0854	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01801 (5)	0.01700 (5)	0.01506 (5)	0.000	0.00225 (3)	0.000
O1	0.0265 (5)	0.0197 (4)	0.0164 (4)	−0.0001 (4)	0.0069 (3)	−0.0005 (3)
O2	0.0255 (5)	0.0200 (4)	0.0196 (4)	0.0001 (4)	0.0043 (4)	0.0005 (3)
N1	0.0254 (6)	0.0323 (6)	0.0174 (5)	−0.0043 (5)	0.0074 (4)	−0.0040 (4)
C1	0.0165 (5)	0.0220 (5)	0.0149 (5)	−0.0002 (4)	0.0020 (4)	−0.0003 (4)
C2	0.0192 (5)	0.0211 (5)	0.0159 (5)	−0.0006 (4)	0.0032 (4)	0.0005 (4)
C3	0.0274 (6)	0.0205 (6)	0.0190 (5)	−0.0004 (5)	0.0067 (5)	−0.0008 (4)
C4	0.0348 (8)	0.0215 (6)	0.0233 (6)	−0.0010 (6)	0.0086 (6)	0.0009 (5)
C5	0.0303 (7)	0.0258 (7)	0.0207 (6)	−0.0034 (5)	0.0077 (5)	0.0018 (5)
C6	0.0191 (5)	0.0250 (6)	0.0162 (5)	−0.0023 (4)	0.0035 (4)	−0.0019 (4)
C7	0.0174 (5)	0.0219 (6)	0.0150 (5)	0.0004 (4)	0.0025 (4)	−0.0009 (4)
C8	0.0197 (5)	0.0205 (6)	0.0210 (6)	0.0003 (4)	0.0016 (4)	−0.0001 (4)
C9	0.0198 (6)	0.0188 (6)	0.0299 (7)	−0.0013 (4)	−0.0012 (5)	0.0019 (5)
C10	0.0210 (6)	0.0233 (6)	0.0286 (7)	0.0013 (5)	−0.0005 (5)	0.0014 (5)
C11	0.0296 (8)	0.0240 (7)	0.0481 (11)	0.0026 (6)	0.0014 (7)	0.0077 (7)
C12	0.0233 (6)	0.0322 (8)	0.0226 (6)	0.0039 (5)	0.0048 (5)	−0.0056 (5)
C13	0.0280 (7)	0.0435 (9)	0.0166 (6)	−0.0043 (6)	0.0061 (5)	−0.0007 (6)

Geometric parameters (Å, º)

Sn1—O1	2.0866 (11)	C7—H7A	0.9300
Sn1—O1^i	2.0866 (11)	C8—C9	1.525 (2)
Sn1—C8	2.1166 (14)	C8—H8A	0.9700
Sn1—C8^i	2.1166 (14)	C8—H8B	0.9700
O1—C1	1.2984 (17)	C9—C10	1.524 (2)
O2—C1	1.2466 (18)	C9—H9A	0.9700
N1—C6	1.3864 (19)	C9—H9B	0.9700
N1—C12	1.457 (2)	C10—C11	1.523 (3)
N1—C13	1.459 (2)	C10—H10A	0.9700
C1—C2	1.4885 (19)	C10—H10B	0.9700
C2—C3	1.390 (2)	C11—H11A	0.9600
C2—C7	1.3949 (19)	C11—H11B	0.9600
C3—C4	1.391 (2)	C11—H11C	0.9600
C3—H3A	0.9300	C12—H12A	0.9600
C4—C5	1.389 (2)	C12—H12B	0.9600
C4—H4A	0.9300	C12—H12C	0.9600
C5—C6	1.404 (2)	C13—H13A	0.9600
C5—H5A	0.9300	C13—H13B	0.9600
C6—C7	1.411 (2)	C13—H13C	0.9600
O1—Sn1—O1^i	82.95 (6)	C9—C8—H8B	108.8
O1—Sn1—C8	107.00 (5)	Sn1—C8—H8B	108.8
O1^i—Sn1—C8	107.47 (5)	H8A—C8—H8B	107.7
O1—Sn1—C8^i	107.48 (5)	C10—C9—C8	112.01 (13)
O1^i—Sn1—C8^i	107.00 (5)	C10—C9—H9A	109.2
C8—Sn1—C8^i	133.40 (8)	C8—C9—H9A	109.2
C1—O1—Sn1	102.81 (9)	C10—C9—H9B	109.2
C6—N1—C12	118.55 (13)	C8—C9—H9B	109.2
C6—N1—C13	118.34 (15)	H9A—C9—H9B	107.9
C12—N1—C13	116.75 (13)	C11—C10—C9	113.18 (14)
O2—C1—O1	119.84 (13)	C11—C10—H10A	108.9
O2—C1—C2	122.95 (13)	C9—C10—H10A	108.9
O1—C1—C2	117.21 (12)	C11—C10—H10B	108.9
C3—C2—C7	121.32 (13)	C9—C10—H10B	108.9
C3—C2—C1	120.32 (12)	H10A—C10—H10B	107.8
C7—C2—C1	118.35 (13)	C10—C11—H11A	109.5
C2—C3—C4	118.23 (14)	C10—C11—H11B	109.5
C2—C3—H3A	120.9	H11A—C11—H11B	109.5
C4—C3—H3A	120.9	C10—C11—H11C	109.5
C5—C4—C3	121.17 (15)	H11A—C11—H11C	109.5
C5—C4—H4A	119.4	H11B—C11—H11C	109.5
C3—C4—H4A	119.4	N1—C12—H12A	109.5
C4—C5—C6	121.23 (14)	N1—C12—H12B	109.5
C4—C5—H5A	119.4	H12A—C12—H12B	109.5
C6—C5—H5A	119.4	N1—C12—H12C	109.5
N1—C6—C5	121.89 (14)	H12A—C12—H12C	109.5
N1—C6—C7	120.73 (14)	H12B—C12—H12C	109.5
C5—C6—C7	117.36 (13)	N1—C13—H13A	109.5
C2—C7—C6	120.63 (13)	N1—C13—H13B	109.5
C2—C7—H7A	119.7	H13A—C13—H13B	109.5
C6—C7—H7A	119.7	N1—C13—H13C	109.5
C9—C8—Sn1	113.72 (10)	H13A—C13—H13C	109.5
C9—C8—H8A	108.8	H13B—C13—H13C	109.5
Sn1—C8—H8A	108.8
O1^i—Sn1—O1—C1	−178.53 (11)	C13—N1—C6—C5	−13.7 (2)
C8—Sn1—O1—C1	75.30 (10)	C12—N1—C6—C7	16.8 (2)
C8^i—Sn1—O1—C1	−72.87 (10)	C13—N1—C6—C7	167.88 (14)
Sn1—O1—C1—O2	−0.92 (15)	C4—C5—C6—N1	−175.93 (15)
Sn1—O1—C1—C2	178.30 (10)	C4—C5—C6—C7	2.5 (2)
O2—C1—C2—C3	175.21 (14)	C3—C2—C7—C6	0.4 (2)
O1—C1—C2—C3	−4.0 (2)	C1—C2—C7—C6	179.68 (12)
O2—C1—C2—C7	−4.0 (2)	N1—C6—C7—C2	176.05 (13)
O1—C1—C2—C7	176.78 (12)	C5—C6—C7—C2	−2.4 (2)
C7—C2—C3—C4	1.5 (2)	O1—Sn1—C8—C9	−139.72 (11)
C1—C2—C3—C4	−177.75 (14)	O1^i—Sn1—C8—C9	132.48 (11)
C2—C3—C4—C5	−1.4 (3)	C8^i—Sn1—C8—C9	−3.55 (10)
C3—C4—C5—C6	−0.7 (3)	Sn1—C8—C9—C10	−174.20 (11)
C12—N1—C6—C5	−164.85 (15)	C8—C9—C10—C11	−179.96 (16)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···Cg1^ii	0.96	2.66	3.567 (2)	157

Symmetry code: (ii) −x, −y+2, −z.