(2-Benzoyl­benzoato)triphenyl­tin(IV)

The structure of the title compound, [Sn(C₆H₅)₃(C₁₄H₉O₃)], consists of monomeric species featuring a distorted tetra­hedral environment around the Sn centre. The tetra­hedral angles are non-equivalent, owing to the relatively close approach of a carboxyl­ate O atom.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.034
• wR factor = 0.095
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Sn     -   O3      ..       8.09 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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: MAR software; cell refinement: marHKL (Klein & Bartels, 2000); data reduction: marHKL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.

(2-Benzoylbenzoato)triphenyltin(IV)

Crystal data

[Sn(C6H5)3(C14H9O3)]	F(000) = 1160
Mr = 575.20	Dx = 1.503 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 5835 reflections
a = 8.761 (3) Å	θ = 3.0–27.5°
b = 17.363 (5) Å	µ = 1.04 mm^−1
c = 17.752 (5) Å	T = 294 K
β = 109.73 (2)°	Parallelipiped, colourless
V = 2541.9 (13) Å^3	0.32 × 0.30 × 0.26 mm
Z = 4

Data collection

Marresearch MAR345 image-plate diffractometer	5667 reflections with I > 2σ(I)
Radiation source: RU200 rotating anode	Rint = 0.039
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 6.66 pixels mm^-1	h = 0→11
188 images, ΔΦ 3° scans	k = −22→0
64928 measured reflections	l = −23→20
5835 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 3.3458P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
5835 reflections	Δρmax = 0.87 e Å^−3
326 parameters	Δρmin = −0.77 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0275 (11)

Special details

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
Sn	0.521950 (18)	0.289494 (9)	0.302662 (9)	0.02543 (9)
O1	0.4959 (2)	0.33041 (10)	0.40830 (10)	0.0276 (3)
C2	0.4036 (3)	0.39189 (14)	0.38780 (15)	0.0268 (5)
O3	0.3639 (2)	0.41772 (11)	0.31894 (11)	0.0322 (4)
C4	0.3463 (3)	0.42648 (14)	0.44979 (15)	0.0278 (5)
C5	0.2682 (3)	0.49800 (15)	0.43343 (17)	0.0324 (5)
H5	0.2552	0.5224	0.3850	0.039*
C6	0.2099 (4)	0.53290 (16)	0.48870 (19)	0.0388 (6)
H6	0.1568	0.5801	0.4770	0.047*
C7	0.2312 (4)	0.49717 (17)	0.56143 (18)	0.0382 (6)
H7	0.1922	0.5204	0.5985	0.046*
C8	0.3103 (3)	0.42722 (17)	0.57891 (17)	0.0353 (6)
H8	0.3254	0.4040	0.6281	0.042*
C9	0.3679 (3)	0.39105 (15)	0.52368 (15)	0.0288 (5)
C10	0.4511 (3)	0.31435 (16)	0.54900 (15)	0.0305 (5)
O11	0.5812 (3)	0.31272 (13)	0.60317 (13)	0.0413 (5)
C12	0.3649 (3)	0.24229 (15)	0.51326 (15)	0.0292 (5)
C13	0.4443 (3)	0.17252 (16)	0.53861 (18)	0.0345 (6)
H13	0.5488	0.1720	0.5757	0.041*
C14	0.3669 (4)	0.10377 (17)	0.5083 (2)	0.0402 (6)
H14	0.4204	0.0572	0.5242	0.048*
C15	0.2097 (4)	0.10474 (17)	0.45437 (19)	0.0404 (6)
H15	0.1577	0.0585	0.4348	0.048*
C16	0.1292 (4)	0.17380 (17)	0.42940 (18)	0.0372 (6)
H16	0.0238	0.1740	0.3932	0.045*
C17	0.2075 (3)	0.24300 (16)	0.45895 (16)	0.0326 (5)
H17	0.1544	0.2896	0.4423	0.039*
C18	0.6482 (3)	0.18513 (14)	0.34921 (15)	0.0268 (5)
C19	0.6748 (3)	0.13239 (15)	0.29527 (16)	0.0317 (5)
H19	0.6435	0.1450	0.2413	0.038*
C20	0.7473 (3)	0.06134 (16)	0.32108 (17)	0.0339 (5)
H20	0.7650	0.0270	0.2847	0.041*
C21	0.7927 (3)	0.04222 (16)	0.40145 (18)	0.0358 (6)
H21	0.8412	−0.0051	0.4191	0.043*
C22	0.7661 (4)	0.09331 (16)	0.45524 (17)	0.0359 (6)
H22	0.7959	0.0800	0.5090	0.043*
C23	0.6947 (3)	0.16494 (15)	0.42956 (16)	0.0311 (5)
H23	0.6783	0.1992	0.4664	0.037*
C24	0.2848 (3)	0.25974 (16)	0.22675 (15)	0.0288 (5)
C25	0.2092 (4)	0.19690 (19)	0.2474 (2)	0.0430 (7)
H25	0.2648	0.1676	0.2922	0.052*
C26	0.0508 (4)	0.1774 (2)	0.2016 (3)	0.0574 (9)
H26	0.0002	0.1358	0.2164	0.069*
C27	−0.0307 (4)	0.2197 (2)	0.1346 (2)	0.0529 (9)
H27	−0.1361	0.2065	0.1038	0.064*
C28	0.0439 (4)	0.2816 (2)	0.1133 (2)	0.0503 (9)
H28	−0.0111	0.3098	0.0677	0.060*
C29	0.2014 (4)	0.30241 (19)	0.15967 (18)	0.0389 (6)
H29	0.2503	0.3449	0.1455	0.047*
C30	0.6713 (3)	0.36543 (14)	0.26500 (15)	0.0270 (5)
C31	0.6128 (3)	0.43465 (16)	0.22592 (17)	0.0339 (5)
H31	0.5053	0.4487	0.2158	0.041*
C32	0.7150 (4)	0.48269 (18)	0.2021 (2)	0.0439 (7)
H32	0.6753	0.5283	0.1752	0.053*
C33	0.8759 (4)	0.4626 (2)	0.2183 (2)	0.0503 (8)
H33	0.9445	0.4953	0.2032	0.060*
C34	0.9352 (4)	0.3940 (2)	0.2568 (2)	0.0468 (7)
H34	1.0432	0.3807	0.2675	0.056*
C35	0.8325 (3)	0.34525 (17)	0.27951 (17)	0.0352 (6)
H35	0.8719	0.2988	0.3046	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.02292 (12)	0.02561 (12)	0.02716 (12)	0.00058 (5)	0.00769 (7)	0.00154 (5)
O1	0.0289 (8)	0.0257 (8)	0.0289 (8)	0.0020 (6)	0.0107 (7)	−0.0002 (7)
C2	0.0235 (10)	0.0261 (11)	0.0304 (12)	−0.0029 (9)	0.0087 (9)	0.0005 (9)
O3	0.0331 (9)	0.0324 (9)	0.0323 (9)	0.0015 (7)	0.0127 (7)	0.0042 (7)
C4	0.0235 (11)	0.0273 (11)	0.0314 (12)	−0.0014 (9)	0.0077 (9)	−0.0009 (9)
C5	0.0312 (12)	0.0280 (12)	0.0374 (13)	0.0007 (10)	0.0108 (10)	0.0009 (10)
C6	0.0362 (14)	0.0298 (13)	0.0487 (16)	0.0042 (11)	0.0120 (12)	−0.0061 (12)
C7	0.0360 (14)	0.0397 (15)	0.0408 (14)	0.0005 (11)	0.0154 (12)	−0.0123 (12)
C8	0.0337 (13)	0.0401 (14)	0.0315 (13)	−0.0008 (11)	0.0102 (10)	−0.0042 (11)
C9	0.0259 (11)	0.0290 (12)	0.0312 (12)	−0.0030 (9)	0.0093 (9)	−0.0026 (9)
C10	0.0292 (12)	0.0351 (13)	0.0274 (12)	−0.0004 (10)	0.0100 (10)	0.0007 (10)
O11	0.0332 (10)	0.0446 (11)	0.0382 (11)	0.0060 (9)	0.0016 (8)	−0.0017 (9)
C12	0.0310 (12)	0.0282 (12)	0.0308 (12)	0.0000 (10)	0.0136 (10)	0.0041 (10)
C13	0.0335 (13)	0.0319 (13)	0.0404 (14)	0.0031 (10)	0.0155 (11)	0.0101 (11)
C14	0.0430 (15)	0.0288 (13)	0.0559 (18)	0.0032 (11)	0.0261 (14)	0.0080 (12)
C15	0.0481 (16)	0.0304 (13)	0.0481 (16)	−0.0067 (12)	0.0233 (13)	−0.0003 (12)
C16	0.0373 (14)	0.0346 (14)	0.0388 (14)	−0.0059 (11)	0.0115 (11)	0.0008 (11)
C17	0.0336 (13)	0.0283 (12)	0.0351 (13)	−0.0012 (10)	0.0103 (10)	0.0039 (10)
C18	0.0236 (11)	0.0246 (11)	0.0306 (12)	0.0017 (9)	0.0069 (9)	0.0033 (9)
C19	0.0289 (12)	0.0329 (13)	0.0310 (12)	0.0001 (10)	0.0073 (10)	−0.0031 (10)
C20	0.0294 (12)	0.0303 (12)	0.0419 (14)	−0.0029 (10)	0.0120 (11)	−0.0092 (11)
C21	0.0328 (13)	0.0260 (12)	0.0480 (15)	−0.0013 (10)	0.0127 (11)	0.0019 (11)
C22	0.0410 (14)	0.0312 (13)	0.0346 (13)	0.0021 (11)	0.0114 (11)	0.0079 (10)
C23	0.0350 (13)	0.0288 (12)	0.0311 (12)	0.0004 (10)	0.0132 (10)	−0.0009 (10)
C24	0.0219 (11)	0.0350 (13)	0.0282 (11)	−0.0018 (9)	0.0069 (9)	−0.0038 (10)
C25	0.0387 (16)	0.0414 (15)	0.0465 (17)	−0.0099 (12)	0.0112 (13)	0.0020 (13)
C26	0.0436 (18)	0.056 (2)	0.072 (2)	−0.0218 (16)	0.0193 (17)	−0.0129 (18)
C27	0.0283 (14)	0.070 (2)	0.055 (2)	−0.0058 (14)	0.0076 (14)	−0.0241 (17)
C28	0.0318 (15)	0.079 (3)	0.0323 (15)	0.0074 (14)	0.0006 (12)	−0.0037 (14)
C29	0.0303 (13)	0.0518 (16)	0.0342 (14)	0.0013 (12)	0.0104 (11)	0.0048 (12)
C30	0.0263 (11)	0.0275 (11)	0.0293 (11)	−0.0042 (9)	0.0123 (9)	−0.0023 (9)
C31	0.0336 (13)	0.0315 (13)	0.0391 (14)	−0.0002 (10)	0.0153 (11)	0.0033 (11)
C32	0.0493 (17)	0.0383 (15)	0.0478 (17)	−0.0089 (13)	0.0211 (14)	0.0046 (13)
C33	0.0461 (17)	0.058 (2)	0.0533 (19)	−0.0207 (15)	0.0255 (15)	−0.0015 (15)
C34	0.0270 (13)	0.069 (2)	0.0480 (17)	−0.0058 (13)	0.0174 (12)	−0.0030 (15)
C35	0.0271 (12)	0.0419 (14)	0.0375 (14)	0.0015 (11)	0.0120 (10)	−0.0016 (11)

Geometric parameters (Å, º)

Sn—O1	2.0885 (18)	C18—C19	1.400 (4)
Sn—C30	2.118 (2)	C19—C20	1.392 (4)
Sn—C24	2.123 (2)	C19—H19	0.9300
Sn—C18	2.138 (2)	C20—C21	1.386 (4)
O1—C2	1.314 (3)	C20—H20	0.9300
C2—O3	1.237 (3)	C21—C22	1.379 (4)
C2—C4	1.482 (3)	C21—H21	0.9300
C4—C5	1.400 (4)	C22—C23	1.398 (4)
C4—C9	1.403 (4)	C22—H22	0.9300
C5—C6	1.389 (4)	C23—H23	0.9300
C5—H5	0.9300	C24—C29	1.383 (4)
C6—C7	1.387 (4)	C24—C25	1.388 (4)
C6—H6	0.9300	C25—C26	1.393 (5)
C7—C8	1.381 (4)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.375 (6)
C8—C9	1.394 (4)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.375 (6)
C9—C10	1.512 (4)	C27—H27	0.9300
C10—O11	1.219 (3)	C28—C29	1.395 (4)
C10—C12	1.488 (4)	C28—H28	0.9300
C12—C17	1.390 (4)	C29—H29	0.9300
C12—C13	1.394 (4)	C30—C35	1.392 (4)
C13—C14	1.388 (4)	C30—C31	1.396 (4)
C13—H13	0.9300	C31—C32	1.390 (4)
C14—C15	1.387 (5)	C31—H31	0.9300
C14—H14	0.9300	C32—C33	1.385 (5)
C15—C16	1.386 (4)	C32—H32	0.9300
C15—H15	0.9300	C33—C34	1.383 (5)
C16—C17	1.395 (4)	C33—H33	0.9300
C16—H16	0.9300	C34—C35	1.391 (4)
C17—H17	0.9300	C34—H34	0.9300
C18—C23	1.390 (4)	C35—H35	0.9300
O1—Sn—C30	109.75 (8)	C20—C19—C18	121.1 (2)
O1—Sn—C24	105.82 (9)	C20—C19—H19	119.4
C30—Sn—C24	121.82 (10)	C18—C19—H19	119.4
O1—Sn—C18	98.06 (8)	C21—C20—C19	119.4 (3)
C30—Sn—C18	110.82 (10)	C21—C20—H20	120.3
C24—Sn—C18	107.86 (10)	C19—C20—H20	120.3
C2—O1—Sn	105.73 (15)	C22—C21—C20	120.1 (3)
O3—C2—O1	120.6 (2)	C22—C21—H21	119.9
O3—C2—C4	122.3 (2)	C20—C21—H21	119.9
O1—C2—C4	117.0 (2)	C21—C22—C23	120.5 (3)
C5—C4—C9	119.0 (2)	C21—C22—H22	119.7
C5—C4—C2	118.0 (2)	C23—C22—H22	119.7
C9—C4—C2	123.0 (2)	C18—C23—C22	120.2 (2)
C6—C5—C4	120.7 (3)	C18—C23—H23	119.9
C6—C5—H5	119.6	C22—C23—H23	119.9
C4—C5—H5	119.6	C29—C24—C25	119.2 (3)
C7—C6—C5	119.8 (3)	C29—C24—Sn	122.4 (2)
C7—C6—H6	120.1	C25—C24—Sn	118.4 (2)
C5—C6—H6	120.1	C24—C25—C26	120.5 (3)
C8—C7—C6	120.2 (3)	C24—C25—H25	119.8
C8—C7—H7	119.9	C26—C25—H25	119.8
C6—C7—H7	119.9	C27—C26—C25	119.9 (3)
C7—C8—C9	120.8 (3)	C27—C26—H26	120.0
C7—C8—H8	119.6	C25—C26—H26	120.0
C9—C8—H8	119.6	C26—C27—C28	120.0 (3)
C8—C9—C4	119.6 (2)	C26—C27—H27	120.0
C8—C9—C10	116.1 (2)	C28—C27—H27	120.0
C4—C9—C10	124.3 (2)	C27—C28—C29	120.5 (3)
O11—C10—C12	121.5 (3)	C27—C28—H28	119.8
O11—C10—C9	118.9 (2)	C29—C28—H28	119.8
C12—C10—C9	119.3 (2)	C24—C29—C28	119.9 (3)
C17—C12—C13	120.1 (3)	C24—C29—H29	120.0
C17—C12—C10	122.0 (2)	C28—C29—H29	120.0
C13—C12—C10	117.8 (2)	C35—C30—C31	119.2 (2)
C14—C13—C12	119.8 (3)	C35—C30—Sn	118.8 (2)
C14—C13—H13	120.1	C31—C30—Sn	122.05 (18)
C12—C13—H13	120.1	C32—C31—C30	120.1 (3)
C15—C14—C13	119.9 (3)	C32—C31—H31	119.9
C15—C14—H14	120.1	C30—C31—H31	119.9
C13—C14—H14	120.1	C33—C32—C31	120.0 (3)
C16—C15—C14	120.7 (3)	C33—C32—H32	120.0
C16—C15—H15	119.6	C31—C32—H32	120.0
C14—C15—H15	119.6	C34—C33—C32	120.4 (3)
C15—C16—C17	119.5 (3)	C34—C33—H33	119.8
C15—C16—H16	120.2	C32—C33—H33	119.8
C17—C16—H16	120.2	C33—C34—C35	119.7 (3)
C12—C17—C16	120.0 (3)	C33—C34—H34	120.1
C12—C17—H17	120.0	C35—C34—H34	120.1
C16—C17—H17	120.0	C34—C35—C30	120.5 (3)
C23—C18—C19	118.6 (2)	C34—C35—H35	119.7
C23—C18—Sn	123.01 (19)	C30—C35—H35	119.7
C19—C18—Sn	118.27 (18)
C30—Sn—O1—C2	70.89 (16)	O1—Sn—C18—C19	172.20 (19)
C24—Sn—O1—C2	−62.27 (17)	C30—Sn—C18—C19	−73.0 (2)
C18—Sn—O1—C2	−173.50 (15)	C24—Sn—C18—C19	62.6 (2)
Sn—O1—C2—O3	−6.5 (3)	C23—C18—C19—C20	−0.5 (4)
Sn—O1—C2—C4	171.63 (17)	Sn—C18—C19—C20	−176.01 (19)
O3—C2—C4—C5	−11.1 (4)	C18—C19—C20—C21	0.5 (4)
O1—C2—C4—C5	170.8 (2)	C19—C20—C21—C22	0.0 (4)
O3—C2—C4—C9	169.3 (2)	C20—C21—C22—C23	−0.6 (4)
O1—C2—C4—C9	−8.8 (3)	C19—C18—C23—C22	−0.1 (4)
C9—C4—C5—C6	−1.2 (4)	Sn—C18—C23—C22	175.2 (2)
C2—C4—C5—C6	179.2 (2)	C21—C22—C23—C18	0.7 (4)
C4—C5—C6—C7	0.9 (4)	O1—Sn—C24—C29	108.6 (2)
C5—C6—C7—C8	0.1 (4)	C30—Sn—C24—C29	−17.5 (3)
C6—C7—C8—C9	−0.8 (4)	C18—Sn—C24—C29	−147.3 (2)
C7—C8—C9—C4	0.5 (4)	O1—Sn—C24—C25	−68.8 (2)
C7—C8—C9—C10	−179.4 (2)	C30—Sn—C24—C25	165.1 (2)
C5—C4—C9—C8	0.5 (4)	C18—Sn—C24—C25	35.3 (3)
C2—C4—C9—C8	−179.9 (2)	C29—C24—C25—C26	−0.6 (5)
C5—C4—C9—C10	−179.5 (2)	Sn—C24—C25—C26	176.9 (3)
C2—C4—C9—C10	0.0 (4)	C24—C25—C26—C27	1.1 (6)
C8—C9—C10—O11	−68.1 (3)	C25—C26—C27—C28	−0.5 (6)
C4—C9—C10—O11	112.0 (3)	C26—C27—C28—C29	−0.7 (6)
C8—C9—C10—C12	105.6 (3)	C25—C24—C29—C28	−0.6 (5)
C4—C9—C10—C12	−74.3 (3)	Sn—C24—C29—C28	−178.0 (2)
O11—C10—C12—C17	171.5 (3)	C27—C28—C29—C24	1.3 (5)
C9—C10—C12—C17	−2.1 (4)	O1—Sn—C30—C35	101.8 (2)
O11—C10—C12—C13	−5.7 (4)	C24—Sn—C30—C35	−133.9 (2)
C9—C10—C12—C13	−179.3 (2)	C18—Sn—C30—C35	−5.4 (2)
C17—C12—C13—C14	1.2 (4)	O1—Sn—C30—C31	−78.5 (2)
C10—C12—C13—C14	178.4 (3)	C24—Sn—C30—C31	45.8 (2)
C12—C13—C14—C15	−1.4 (4)	C18—Sn—C30—C31	174.3 (2)
C13—C14—C15—C16	0.9 (5)	C35—C30—C31—C32	−0.1 (4)
C14—C15—C16—C17	0.0 (4)	Sn—C30—C31—C32	−179.8 (2)
C13—C12—C17—C16	−0.4 (4)	C30—C31—C32—C33	−1.1 (5)
C10—C12—C17—C16	−177.5 (2)	C31—C32—C33—C34	1.3 (5)
C15—C16—C17—C12	−0.2 (4)	C32—C33—C34—C35	−0.2 (5)
O1—Sn—C18—C23	−3.1 (2)	C33—C34—C35—C30	−1.1 (5)
C30—Sn—C18—C23	111.6 (2)	C31—C30—C35—C34	1.2 (4)
C24—Sn—C18—C23	−112.7 (2)	Sn—C30—C35—C34	−179.0 (2)