(3-Amino-4-chloro­benzoato)triphenyl­tin(IV)

The structure of the title compound, [Sn(C₆H₅)₃(C₇H₅ClNO₂)], contains dimeric units that are stabilized by inter- and intra­molecular hydrogen bonds involving amino H atoms and carbonyl O and Cl atoms. The geometry around Sn is slightly distorted tetra­hedral and the Sn—C distances are essentially identical.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.034
• wR factor = 0.082
• Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(3-Amino-4-chlorobenzoato)triphenyltin(IV)

Crystal data

[Sn(C6H5)3(C7H5ClNO2)]	F(000) = 2080
Mr = 520.56	Dx = 1.525 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 100329 reflections
a = 17.210 (4) Å	θ = 3.2–27.5°
b = 11.629 (3) Å	µ = 1.27 mm^−1
c = 23.205 (6) Å	T = 173 K
β = 102.507 (15)°	Block, colorless
V = 4534 (2) Å^3	0.12 × 0.10 × 0.08 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	5184 independent reflections
Radiation source: fine-focus sealed tube	3962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω and φ scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −21→22
Tmin = 0.863, Tmax = 0.906	k = −15→14
10032 measured reflections	l = −30→30

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) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 1.24P] where P = (Fo^2 + 2Fc^2)/3
5184 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.82 e Å^−3
0 restraints	Δρmin = −0.65 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.448753 (11)	0.062848 (16)	0.109095 (8)	0.02564 (8)
Cl1	0.09529 (4)	−0.00277 (7)	−0.21795 (3)	0.03758 (19)
O1	0.37334 (12)	0.06299 (16)	0.02766 (9)	0.0340 (5)
O2	0.32154 (12)	−0.10134 (19)	0.05186 (9)	0.0369 (5)
N1	0.11531 (16)	−0.1997 (2)	−0.13511 (12)	0.0454 (7)
H1A	0.1179	−0.2619	−0.1131	0.055*
H1B	0.0828	−0.1975	−0.1700	0.055*
C1	0.51260 (16)	0.2125 (2)	0.09477 (12)	0.0263 (6)
C2	0.59220 (17)	0.2055 (3)	0.09055 (12)	0.0309 (7)
H2	0.6185	0.1322	0.0951	0.037*
C3	0.63302 (19)	0.3029 (3)	0.07985 (15)	0.0415 (8)
H3	0.6876	0.2977	0.0766	0.050*
C4	0.5956 (2)	0.4081 (3)	0.07289 (19)	0.0542 (11)
H4	0.6244	0.4752	0.0655	0.065*
C5	0.5172 (2)	0.4167 (3)	0.0776 (2)	0.0588 (12)
H5	0.4918	0.4906	0.0735	0.071*
C6	0.47621 (19)	0.3203 (3)	0.08801 (15)	0.0405 (8)
H6	0.4215	0.3269	0.0908	0.049*
C7	0.38051 (16)	0.0866 (2)	0.17413 (13)	0.0274 (6)
C8	0.39694 (17)	0.1803 (3)	0.21165 (13)	0.0322 (7)
H8	0.4369	0.2347	0.2065	0.039*
C9	0.35514 (19)	0.1980 (3)	0.25630 (14)	0.0388 (8)
H9	0.3670	0.2626	0.2825	0.047*
C10	0.29689 (18)	0.1208 (3)	0.26324 (14)	0.0401 (8)
H10	0.2677	0.1325	0.2936	0.048*
C11	0.28053 (19)	0.0263 (3)	0.22647 (15)	0.0440 (8)
H11	0.2398	−0.0270	0.2313	0.053*
C12	0.32212 (18)	0.0084 (3)	0.18217 (14)	0.0360 (7)
H12	0.3108	−0.0578	0.1571	0.043*
C13	0.51757 (16)	−0.0901 (2)	0.11998 (13)	0.0273 (6)
C14	0.55751 (18)	−0.1198 (3)	0.17666 (14)	0.0362 (7)
H14	0.5541	−0.0703	0.2091	0.043*
C15	0.6013 (2)	−0.2208 (3)	0.18666 (16)	0.0471 (9)
H15	0.6289	−0.2403	0.2260	0.057*
C16	0.6057 (2)	−0.2920 (3)	0.14035 (17)	0.0481 (9)
H16	0.6357	−0.3622	0.1470	0.058*
C17	0.56648 (19)	−0.2633 (3)	0.08336 (16)	0.0429 (8)
H17	0.5698	−0.3128	0.0509	0.051*
C18	0.52294 (18)	−0.1627 (3)	0.07337 (14)	0.0343 (7)
H18	0.4959	−0.1434	0.0339	0.041*
C19	0.32228 (16)	−0.0224 (3)	0.01683 (13)	0.0284 (6)
C20	0.26582 (15)	−0.0155 (2)	−0.04141 (12)	0.0254 (6)
C21	0.21399 (15)	−0.1064 (3)	−0.05994 (12)	0.0256 (6)
H21	0.2129	−0.1711	−0.0344	0.031*
C22	0.16189 (16)	−0.1063 (3)	−0.11491 (13)	0.0273 (6)
C23	0.16184 (15)	−0.0078 (3)	−0.14992 (12)	0.0261 (6)
C24	0.21327 (16)	0.0828 (2)	−0.13199 (14)	0.0308 (7)
H24	0.2130	0.1479	−0.1575	0.037*
C25	0.26543 (17)	0.0793 (2)	−0.07809 (13)	0.0313 (7)
H25	0.3019	0.1415	−0.0655	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.02476 (11)	0.02769 (12)	0.02374 (12)	−0.00404 (8)	0.00363 (8)	0.00116 (8)
Cl1	0.0303 (4)	0.0441 (5)	0.0326 (4)	−0.0028 (4)	−0.0057 (3)	0.0024 (4)
O1	0.0331 (11)	0.0351 (12)	0.0289 (12)	−0.0117 (9)	−0.0041 (9)	0.0014 (9)
O2	0.0369 (12)	0.0395 (12)	0.0297 (12)	−0.0092 (10)	−0.0029 (9)	0.0074 (10)
N1	0.0502 (16)	0.0387 (16)	0.0394 (17)	−0.0227 (14)	−0.0078 (13)	0.0065 (13)
C1	0.0272 (14)	0.0265 (15)	0.0246 (16)	−0.0067 (12)	0.0045 (12)	−0.0027 (12)
C2	0.0314 (15)	0.0339 (17)	0.0288 (17)	−0.0021 (13)	0.0097 (13)	−0.0041 (13)
C3	0.0351 (17)	0.041 (2)	0.054 (2)	−0.0092 (15)	0.0212 (16)	−0.0066 (16)
C4	0.060 (2)	0.0320 (19)	0.081 (3)	−0.0147 (18)	0.039 (2)	−0.0052 (19)
C5	0.059 (2)	0.0281 (19)	0.099 (3)	0.0026 (17)	0.039 (2)	0.0066 (19)
C6	0.0355 (17)	0.0327 (18)	0.059 (2)	0.0003 (14)	0.0226 (17)	0.0025 (16)
C7	0.0268 (15)	0.0314 (16)	0.0237 (16)	0.0033 (12)	0.0047 (12)	0.0048 (12)
C8	0.0320 (15)	0.0332 (17)	0.0311 (17)	0.0003 (14)	0.0064 (13)	0.0069 (14)
C9	0.0464 (19)	0.0411 (19)	0.0282 (18)	0.0074 (16)	0.0063 (15)	0.0028 (14)
C10	0.0379 (18)	0.053 (2)	0.0324 (19)	0.0078 (17)	0.0147 (15)	0.0082 (16)
C11	0.0345 (18)	0.058 (2)	0.043 (2)	−0.0061 (17)	0.0149 (16)	0.0109 (18)
C12	0.0338 (16)	0.0393 (19)	0.0352 (18)	−0.0028 (15)	0.0079 (14)	0.0028 (15)
C13	0.0230 (14)	0.0264 (15)	0.0311 (17)	−0.0065 (12)	0.0030 (12)	0.0013 (12)
C14	0.0399 (18)	0.0315 (17)	0.0327 (18)	0.0008 (15)	−0.0021 (14)	0.0000 (14)
C15	0.050 (2)	0.041 (2)	0.045 (2)	0.0030 (17)	0.0005 (17)	0.0078 (17)
C16	0.048 (2)	0.0318 (19)	0.064 (3)	0.0057 (16)	0.0116 (19)	0.0083 (18)
C17	0.048 (2)	0.0345 (19)	0.051 (2)	−0.0030 (16)	0.0201 (18)	−0.0054 (16)
C18	0.0394 (17)	0.0342 (18)	0.0292 (18)	−0.0064 (14)	0.0075 (14)	−0.0024 (14)
C19	0.0229 (14)	0.0331 (16)	0.0284 (16)	−0.0015 (13)	0.0040 (12)	−0.0002 (14)
C20	0.0199 (13)	0.0269 (15)	0.0291 (16)	−0.0005 (12)	0.0043 (12)	0.0007 (13)
C21	0.0257 (14)	0.0272 (15)	0.0242 (16)	−0.0013 (12)	0.0056 (12)	0.0035 (12)
C22	0.0222 (14)	0.0293 (15)	0.0315 (17)	−0.0029 (12)	0.0082 (12)	−0.0034 (13)
C23	0.0203 (13)	0.0318 (16)	0.0239 (16)	0.0023 (12)	0.0001 (11)	−0.0031 (13)
C24	0.0254 (15)	0.0274 (16)	0.0372 (19)	−0.0005 (12)	0.0012 (13)	0.0066 (13)
C25	0.0261 (15)	0.0312 (17)	0.0336 (18)	−0.0040 (12)	−0.0001 (13)	0.0005 (13)

Geometric parameters (Å, º)

Sn1—O1	2.048 (2)	C10—C11	1.382 (5)
Sn1—C7	2.122 (3)	C10—H10	0.9600
Sn1—C13	2.121 (3)	C11—C12	1.390 (4)
Sn1—C1	2.123 (3)	C11—H11	0.9602
Cl1—C23	1.739 (3)	C12—H12	0.9600
O1—C19	1.314 (3)	C13—C14	1.389 (4)
O2—C19	1.228 (3)	C13—C18	1.391 (4)
N1—C22	1.371 (4)	C14—C15	1.387 (4)
N1—H1A	0.8800	C14—H14	0.9600
N1—H1B	0.8800	C15—C16	1.372 (5)
C1—C6	1.395 (4)	C15—H15	0.9600
C1—C2	1.397 (4)	C16—C17	1.389 (5)
C2—C3	1.384 (4)	C16—H16	0.9600
C2—H2	0.9600	C17—C18	1.381 (4)
C3—C4	1.375 (5)	C17—H17	0.9599
C3—H3	0.9601	C18—H18	0.9600
C4—C5	1.382 (5)	C19—C20	1.486 (4)
C4—H4	0.9601	C20—C21	1.390 (4)
C5—C6	1.372 (4)	C20—C25	1.392 (4)
C5—H5	0.9599	C21—C22	1.391 (4)
C6—H6	0.9600	C21—H21	0.9600
C7—C8	1.385 (4)	C22—C23	1.404 (4)
C7—C12	1.397 (4)	C23—C24	1.381 (4)
C8—C9	1.399 (4)	C24—C25	1.373 (4)
C8—H8	0.9600	C24—H24	0.9599
C9—C10	1.381 (4)	C25—H25	0.9600
C9—H9	0.9601
O1—Sn1—C7	108.57 (10)	C11—C12—C7	120.1 (3)
O1—Sn1—C13	109.67 (10)	C11—C12—H12	120.0
C7—Sn1—C13	113.91 (11)	C7—C12—H12	119.9
O1—Sn1—C1	95.79 (9)	C14—C13—C18	118.8 (3)
C7—Sn1—C1	112.94 (11)	C14—C13—Sn1	118.1 (2)
C13—Sn1—C1	114.30 (11)	C18—C13—Sn1	123.1 (2)
C19—O1—Sn1	116.10 (18)	C15—C14—C13	120.6 (3)
C22—N1—H1A	120.0	C15—C14—H14	120.0
C22—N1—H1B	120.0	C13—C14—H14	119.4
H1A—N1—H1B	120.0	C16—C15—C14	120.0 (3)
C6—C1—C2	117.9 (3)	C16—C15—H15	120.2
C6—C1—Sn1	121.3 (2)	C14—C15—H15	119.8
C2—C1—Sn1	120.8 (2)	C15—C16—C17	120.2 (3)
C3—C2—C1	120.5 (3)	C15—C16—H16	120.4
C3—C2—H2	120.1	C17—C16—H16	119.4
C1—C2—H2	119.3	C18—C17—C16	119.8 (3)
C4—C3—C2	120.4 (3)	C18—C17—H17	119.9
C4—C3—H3	119.2	C16—C17—H17	120.2
C2—C3—H3	120.4	C17—C18—C13	120.6 (3)
C3—C4—C5	119.7 (3)	C17—C18—H18	119.4
C3—C4—H4	119.8	C13—C18—H18	120.0
C5—C4—H4	120.4	O2—C19—O1	122.7 (3)
C6—C5—C4	120.2 (3)	O2—C19—C20	123.0 (3)
C6—C5—H5	120.6	O1—C19—C20	114.3 (2)
C4—C5—H5	119.2	C21—C20—C25	119.7 (3)
C5—C6—C1	121.2 (3)	C21—C20—C19	119.3 (3)
C5—C6—H6	119.6	C25—C20—C19	121.0 (3)
C1—C6—H6	119.1	C22—C21—C20	121.7 (3)
C8—C7—C12	118.9 (3)	C22—C21—H21	118.1
C8—C7—Sn1	118.7 (2)	C20—C21—H21	120.1
C12—C7—Sn1	122.4 (2)	N1—C22—C21	121.7 (3)
C7—C8—C9	120.9 (3)	N1—C22—C23	121.4 (3)
C7—C8—H8	119.6	C21—C22—C23	116.8 (3)
C9—C8—H8	119.4	C24—C23—C22	121.9 (3)
C10—C9—C8	119.6 (3)	C24—C23—Cl1	120.1 (2)
C10—C9—H9	119.7	C22—C23—Cl1	118.1 (2)
C8—C9—H9	120.8	C25—C24—C23	120.1 (3)
C11—C10—C9	120.1 (3)	C25—C24—H24	119.9
C11—C10—H10	119.8	C23—C24—H24	119.9
C9—C10—H10	120.1	C24—C25—C20	119.7 (3)
C10—C11—C12	120.5 (3)	C24—C25—H25	120.7
C10—C11—H11	119.9	C20—C25—H25	119.6
C12—C11—H11	119.6
C7—Sn1—O1—C19	−65.3 (2)	C7—Sn1—C13—C14	−42.5 (3)
C13—Sn1—O1—C19	59.8 (2)	C1—Sn1—C13—C14	89.4 (2)
C1—Sn1—O1—C19	178.1 (2)	O1—Sn1—C13—C18	14.1 (3)
O1—Sn1—C1—C6	66.7 (3)	C7—Sn1—C13—C18	136.0 (2)
C7—Sn1—C1—C6	−46.3 (3)	C1—Sn1—C13—C18	−92.1 (2)
C13—Sn1—C1—C6	−178.7 (2)	C18—C13—C14—C15	−0.6 (4)
O1—Sn1—C1—C2	−111.9 (2)	Sn1—C13—C14—C15	177.9 (2)
C7—Sn1—C1—C2	135.1 (2)	C13—C14—C15—C16	0.3 (5)
C13—Sn1—C1—C2	2.7 (3)	C14—C15—C16—C17	0.0 (5)
C6—C1—C2—C3	−0.2 (4)	C15—C16—C17—C18	0.0 (5)
Sn1—C1—C2—C3	178.5 (2)	C16—C17—C18—C13	−0.4 (4)
C1—C2—C3—C4	−0.3 (5)	C14—C13—C18—C17	0.7 (4)
C2—C3—C4—C5	1.1 (6)	Sn1—C13—C18—C17	−177.8 (2)
C3—C4—C5—C6	−1.4 (7)	Sn1—O1—C19—O2	−3.4 (4)
C4—C5—C6—C1	0.9 (6)	Sn1—O1—C19—C20	176.79 (17)
C2—C1—C6—C5	−0.1 (5)	O2—C19—C20—C21	−5.7 (4)
Sn1—C1—C6—C5	−178.8 (3)	O1—C19—C20—C21	174.1 (2)
O1—Sn1—C7—C8	−121.0 (2)	O2—C19—C20—C25	175.8 (3)
C13—Sn1—C7—C8	116.5 (2)	O1—C19—C20—C25	−4.4 (4)
C1—Sn1—C7—C8	−16.1 (3)	C25—C20—C21—C22	0.8 (4)
O1—Sn1—C7—C12	61.9 (3)	C19—C20—C21—C22	−177.7 (2)
C13—Sn1—C7—C12	−60.6 (3)	C20—C21—C22—N1	174.7 (3)
C1—Sn1—C7—C12	166.8 (2)	C20—C21—C22—C23	−2.5 (4)
C12—C7—C8—C9	−1.0 (4)	N1—C22—C23—C24	−174.5 (3)
Sn1—C7—C8—C9	−178.2 (2)	C21—C22—C23—C24	2.7 (4)
C7—C8—C9—C10	0.3 (4)	N1—C22—C23—Cl1	4.7 (4)
C8—C9—C10—C11	0.4 (5)	C21—C22—C23—Cl1	−178.05 (19)
C9—C10—C11—C12	−0.3 (5)	C22—C23—C24—C25	−1.2 (4)
C10—C11—C12—C7	−0.6 (5)	Cl1—C23—C24—C25	179.5 (2)
C8—C7—C12—C11	1.2 (5)	C23—C24—C25—C20	−0.5 (4)
Sn1—C7—C12—C11	178.3 (2)	C21—C20—C25—C24	0.7 (4)
O1—Sn1—C13—C14	−164.4 (2)	C19—C20—C25—C24	179.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.88	2.24	3.059 (3)	156
N1—H1B···Cl1	0.88	2.55	2.962 (3)	109

Symmetry code: (i) −x+1/2, −y−1/2, −z.