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The title compound, [Sn(C
4H
9)
2(C
7H
5N
2O
4)
2], has twofold rotation symmetry, and two 2-amino-5-nitrobenzoate ligands are chelated to the dibutyltin unit through both O atoms of the carboxylate group in a six-coordinate environment. There are intra- and intermolecular N—H
O hydrogen bonds, forming one-dimensional chains parallel to the
b axis.
Supporting information
CCDC reference: 296621
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.022
- wR factor = 0.060
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O3 .. 7.60 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6
C7 -SN1 -O3 -C7 3.20 0.50 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 38
C1 -C6 -C7 -SN1 -13.00 1.10 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 39
C5 -C6 -C7 -SN1 165.90 0.80 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 44
O3 -SN1 -C7 -O3 178.40 0.20 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 50
O3 -SN1 -C7 -O4 -3.20 0.40 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 52
O4 -SN1 -C7 -C6 10.80 0.90 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 53
O4 -SN1 -C7 -C6 9.60 1.00 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 54
C8 -SN1 -C7 -C6 116.50 0.90 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 55
C8 -SN1 -C7 -C6 -98.10 0.90 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 56
O3 -SN1 -C7 -C6 -170.90 1.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 57
O3 -SN1 -C7 -C6 7.50 1.20 2.655 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 58
C7 -SN1 -C7 -C6 10.00 0.90 2.655 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
13 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
12 ALERT type 4 Improvement, methodology, query or suggestion
A solution of di-n-butyltin(IV) oxide (0.75 g, 3 mmol) and (2-amino-5-nitro)benzoic acid (1.09 g, 6 mmol) in methanol (60 ml) was refluxed for ca 4 h. The water formed during the reaction was removed by azeotropic dehydration using a Dean and Stark apparatus. The clear yellow solution was filtered and left for evaporation at room temperature. Yellow crystals were obtained after two weeks (yield 1.60 g, 90%; m.p. 482–483 K). Analysis found: C 43.91, H 4.46, N 8.85, Sn 19.08%; calculated: C 44.3, H 4.7, N 9.4, Sn 19.9%.
H atoms were located in difference-density maps and repositioned geometrically, with N—H = 0.86 Å and C—H = 0.93–0.97 Å. They were constrained to ride on their parent atoms, with Uiso(H) values of 1.2 (1.5 for methyl) times Ueq(C,N).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); 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).
Bis(2-amino-5-nitrobenzoato-
κ2O,
O')di-n-butyltin(IV)
top
Crystal data top
[Sn(C4H9)2(C7H5N2O4)2] | F(000) = 1208 |
Mr = 595.17 | Dx = 1.581 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5761 reflections |
a = 14.356 (4) Å | θ = 2.1–25.5° |
b = 9.006 (2) Å | µ = 1.08 mm−1 |
c = 20.155 (5) Å | T = 298 K |
β = 106.305 (4)° | Block, light yellow |
V = 2501.0 (11) Å3 | 0.48 × 0.44 × 0.18 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2328 independent reflections |
Radiation source: fine-focus sealed tube | 2257 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.5°, θmin = 2.1° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −10→10 |
Tmin = 0.626, Tmax = 0.830 | l = −19→24 |
6494 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0309P)2 + 2.0841P] where P = (Fo2 + 2Fc2)/3 |
2328 reflections | (Δ/σ)max < 0.001 |
160 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
[Sn(C4H9)2(C7H5N2O4)2] | V = 2501.0 (11) Å3 |
Mr = 595.17 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 14.356 (4) Å | µ = 1.08 mm−1 |
b = 9.006 (2) Å | T = 298 K |
c = 20.155 (5) Å | 0.48 × 0.44 × 0.18 mm |
β = 106.305 (4)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2328 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2257 reflections with I > 2σ(I) |
Tmin = 0.626, Tmax = 0.830 | Rint = 0.015 |
6494 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.43 e Å−3 |
2328 reflections | Δρmin = −0.29 e Å−3 |
160 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sn1 | 0.5000 | 0.32559 (2) | 0.2500 | 0.03777 (9) | |
O1 | 0.6125 (2) | −0.3002 (2) | 0.08958 (11) | 0.0802 (7) | |
O2 | 0.63931 (16) | −0.30009 (18) | −0.01057 (11) | 0.0608 (5) | |
O3 | 0.56250 (13) | 0.36944 (17) | 0.14951 (8) | 0.0474 (4) | |
O4 | 0.53727 (13) | 0.15268 (16) | 0.19048 (9) | 0.0462 (4) | |
N1 | 0.62603 (15) | −0.2351 (2) | 0.03967 (10) | 0.0475 (5) | |
N2 | 0.61462 (16) | 0.3828 (2) | 0.03276 (11) | 0.0489 (5) | |
H2A | 0.6295 | 0.4278 | −0.0004 | 0.059* | |
H2B | 0.5982 | 0.4331 | 0.0639 | 0.059* | |
C1 | 0.59740 (15) | 0.0002 (2) | 0.09032 (10) | 0.0363 (4) | |
H1 | 0.5822 | −0.0528 | 0.1255 | 0.044* | |
C2 | 0.62367 (15) | −0.0744 (2) | 0.03885 (11) | 0.0366 (4) | |
C3 | 0.64635 (15) | 0.0011 (2) | −0.01463 (11) | 0.0404 (5) | |
H3 | 0.6636 | −0.0509 | −0.0493 | 0.048* | |
C4 | 0.64298 (17) | 0.1525 (2) | −0.01568 (12) | 0.0409 (5) | |
H4 | 0.6584 | 0.2031 | −0.0514 | 0.049* | |
C5 | 0.61668 (15) | 0.2344 (2) | 0.03606 (11) | 0.0349 (4) | |
C6 | 0.59348 (15) | 0.1543 (2) | 0.09002 (11) | 0.0343 (4) | |
C7 | 0.56347 (15) | 0.2308 (2) | 0.14539 (11) | 0.0379 (4) | |
C8 | 0.36507 (17) | 0.3994 (3) | 0.18379 (12) | 0.0498 (5) | |
H8A | 0.3509 | 0.3427 | 0.1412 | 0.060* | |
H8B | 0.3145 | 0.3780 | 0.2057 | 0.060* | |
C9 | 0.36097 (18) | 0.5645 (3) | 0.16583 (13) | 0.0509 (6) | |
H9A | 0.4179 | 0.5900 | 0.1513 | 0.061* | |
H9B | 0.3043 | 0.5827 | 0.1271 | 0.061* | |
C10 | 0.3566 (3) | 0.6646 (3) | 0.22498 (16) | 0.0672 (8) | |
H10A | 0.4137 | 0.6477 | 0.2635 | 0.081* | |
H10B | 0.3002 | 0.6385 | 0.2400 | 0.081* | |
C11 | 0.3512 (3) | 0.8279 (3) | 0.20626 (19) | 0.0800 (10) | |
H11A | 0.4068 | 0.8547 | 0.1913 | 0.120* | |
H11B | 0.3501 | 0.8860 | 0.2460 | 0.120* | |
H11C | 0.2932 | 0.8465 | 0.1696 | 0.120* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.05394 (14) | 0.02975 (12) | 0.03378 (13) | 0.000 | 0.01916 (9) | 0.000 |
O1 | 0.159 (2) | 0.0303 (9) | 0.0612 (13) | 0.0036 (11) | 0.0474 (14) | 0.0064 (8) |
O2 | 0.0945 (14) | 0.0327 (8) | 0.0643 (12) | 0.0017 (8) | 0.0372 (11) | −0.0120 (8) |
O3 | 0.0742 (11) | 0.0294 (7) | 0.0471 (9) | −0.0030 (7) | 0.0311 (8) | −0.0051 (7) |
O4 | 0.0734 (11) | 0.0309 (7) | 0.0440 (9) | −0.0004 (7) | 0.0325 (8) | 0.0001 (6) |
N1 | 0.0650 (12) | 0.0284 (9) | 0.0495 (11) | 0.0007 (9) | 0.0170 (9) | −0.0032 (9) |
N2 | 0.0780 (13) | 0.0277 (9) | 0.0528 (12) | −0.0005 (9) | 0.0375 (10) | 0.0030 (8) |
C1 | 0.0455 (11) | 0.0287 (10) | 0.0345 (10) | −0.0024 (8) | 0.0112 (9) | 0.0014 (8) |
C2 | 0.0443 (11) | 0.0255 (10) | 0.0394 (11) | −0.0001 (8) | 0.0110 (9) | −0.0028 (8) |
C3 | 0.0490 (11) | 0.0348 (11) | 0.0409 (11) | −0.0011 (9) | 0.0185 (9) | −0.0079 (9) |
C4 | 0.0538 (12) | 0.0351 (11) | 0.0396 (12) | −0.0035 (9) | 0.0227 (10) | 0.0006 (9) |
C5 | 0.0408 (10) | 0.0282 (10) | 0.0376 (11) | −0.0020 (8) | 0.0143 (8) | −0.0004 (8) |
C6 | 0.0415 (10) | 0.0283 (10) | 0.0347 (10) | −0.0019 (8) | 0.0134 (9) | −0.0024 (8) |
C7 | 0.0487 (11) | 0.0315 (10) | 0.0367 (11) | −0.0003 (9) | 0.0169 (9) | −0.0013 (9) |
C8 | 0.0526 (13) | 0.0509 (14) | 0.0446 (13) | −0.0031 (11) | 0.0115 (10) | 0.0006 (11) |
C9 | 0.0532 (13) | 0.0529 (14) | 0.0443 (13) | 0.0043 (11) | 0.0096 (10) | 0.0043 (11) |
C10 | 0.084 (2) | 0.0632 (18) | 0.0528 (16) | 0.0108 (14) | 0.0166 (15) | −0.0017 (13) |
C11 | 0.104 (3) | 0.0575 (19) | 0.071 (2) | 0.0115 (16) | 0.0132 (19) | −0.0082 (14) |
Geometric parameters (Å, º) top
Sn1—O4 | 2.1238 (15) | C2—C3 | 1.388 (3) |
Sn1—O4i | 2.1238 (15) | C3—C4 | 1.364 (3) |
Sn1—C8i | 2.127 (2) | C3—H3 | 0.9300 |
Sn1—C8 | 2.127 (2) | C4—C5 | 1.413 (3) |
Sn1—O3 | 2.4665 (16) | C4—H4 | 0.9300 |
Sn1—O3i | 2.4665 (16) | C5—C6 | 1.420 (3) |
Sn1—C7 | 2.662 (2) | C6—C7 | 1.475 (3) |
Sn1—C7i | 2.662 (2) | C8—C9 | 1.527 (3) |
O1—N1 | 1.226 (3) | C8—H8A | 0.9700 |
O2—N1 | 1.230 (3) | C8—H8B | 0.9700 |
O3—C7 | 1.252 (3) | C9—C10 | 1.510 (4) |
O4—C7 | 1.286 (3) | C9—H9A | 0.9700 |
N1—C2 | 1.448 (3) | C9—H9B | 0.9700 |
N2—C5 | 1.338 (3) | C10—C11 | 1.515 (4) |
N2—H2A | 0.8584 | C10—H10A | 0.9700 |
N2—H2B | 0.8584 | C10—H10B | 0.9700 |
C1—C2 | 1.374 (3) | C11—H11A | 0.9600 |
C1—C6 | 1.390 (3) | C11—H11B | 0.9600 |
C1—H1 | 0.9300 | C11—H11C | 0.9600 |
| | | |
O4—Sn1—O4i | 85.68 (8) | C4—C3—C2 | 119.1 (2) |
O4—Sn1—C8i | 104.72 (8) | C4—C3—H3 | 120.4 |
O4i—Sn1—C8i | 101.79 (9) | C2—C3—H3 | 120.4 |
O4—Sn1—C8 | 101.79 (9) | C3—C4—C5 | 121.8 (2) |
O4i—Sn1—C8 | 104.72 (8) | C3—C4—H4 | 119.1 |
C8i—Sn1—C8 | 143.56 (14) | C5—C4—H4 | 119.1 |
O4—Sn1—O3 | 56.37 (6) | N2—C5—C4 | 119.47 (19) |
O4i—Sn1—O3 | 142.05 (5) | N2—C5—C6 | 122.59 (18) |
C8i—Sn1—O3 | 89.31 (8) | C4—C5—C6 | 117.94 (18) |
C8—Sn1—O3 | 84.95 (8) | C1—C6—C5 | 119.53 (19) |
O4—Sn1—O3i | 142.05 (5) | C1—C6—C7 | 118.89 (19) |
O4i—Sn1—O3i | 56.37 (6) | C5—C6—C7 | 121.57 (18) |
C8i—Sn1—O3i | 84.95 (8) | O3—C7—O4 | 119.19 (18) |
C8—Sn1—O3i | 89.31 (8) | O3—C7—C6 | 121.80 (18) |
O3—Sn1—O3i | 161.57 (7) | O4—C7—C6 | 119.01 (18) |
O4—Sn1—C7 | 28.45 (6) | O3—C7—Sn1 | 67.34 (11) |
O4i—Sn1—C7 | 114.13 (6) | O4—C7—Sn1 | 51.87 (10) |
C8i—Sn1—C7 | 98.24 (8) | C6—C7—Sn1 | 170.73 (15) |
C8—Sn1—C7 | 93.29 (8) | C9—C8—Sn1 | 114.88 (16) |
O3—Sn1—C7 | 27.93 (6) | C9—C8—H8A | 108.5 |
O3i—Sn1—C7 | 170.49 (6) | Sn1—C8—H8A | 108.5 |
O4—Sn1—C7i | 114.13 (6) | C9—C8—H8B | 108.5 |
O4i—Sn1—C7i | 28.45 (6) | Sn1—C8—H8B | 108.5 |
C8i—Sn1—C7i | 93.29 (8) | H8A—C8—H8B | 107.5 |
C8—Sn1—C7i | 98.24 (8) | C10—C9—C8 | 113.7 (2) |
O3—Sn1—C7i | 170.49 (6) | C10—C9—H9A | 108.8 |
O3i—Sn1—C7i | 27.93 (6) | C8—C9—H9A | 108.8 |
C7—Sn1—C7i | 142.58 (9) | C10—C9—H9B | 108.8 |
C7—O3—Sn1 | 84.73 (12) | C8—C9—H9B | 108.8 |
C7—O4—Sn1 | 99.68 (12) | H9A—C9—H9B | 107.7 |
O1—N1—O2 | 123.0 (2) | C9—C10—C11 | 113.2 (3) |
O1—N1—C2 | 118.61 (19) | C9—C10—H10A | 108.9 |
O2—N1—C2 | 118.34 (19) | C11—C10—H10A | 108.9 |
C5—N2—H2A | 120.2 | C9—C10—H10B | 108.9 |
C5—N2—H2B | 119.8 | C11—C10—H10B | 108.9 |
H2A—N2—H2B | 120.0 | H10A—C10—H10B | 107.8 |
C2—C1—C6 | 120.27 (19) | C10—C11—H11A | 109.5 |
C2—C1—H1 | 119.9 | C10—C11—H11B | 109.5 |
C6—C1—H1 | 119.9 | H11A—C11—H11B | 109.5 |
C1—C2—C3 | 121.40 (19) | C10—C11—H11C | 109.5 |
C1—C2—N1 | 119.35 (19) | H11A—C11—H11C | 109.5 |
C3—C2—N1 | 119.24 (18) | H11B—C11—H11C | 109.5 |
| | | |
O4—Sn1—O3—C7 | 0.93 (12) | C5—C6—C7—O3 | −4.2 (3) |
O4i—Sn1—O3—C7 | 0.72 (18) | C1—C6—C7—O4 | −3.3 (3) |
C8i—Sn1—O3—C7 | 109.19 (14) | C5—C6—C7—O4 | 175.57 (19) |
C8—Sn1—O3—C7 | −106.83 (14) | C1—C6—C7—Sn1 | −13.0 (11) |
O3i—Sn1—O3—C7 | −179.16 (13) | C5—C6—C7—Sn1 | 165.9 (8) |
C7i—Sn1—O3—C7 | 3.2 (5) | O4—Sn1—C7—O3 | −178.4 (2) |
O4i—Sn1—O4—C7 | 178.95 (17) | O4i—Sn1—C7—O3 | −179.52 (12) |
C8i—Sn1—O4—C7 | −79.98 (15) | C8i—Sn1—C7—O3 | −72.59 (14) |
C8—Sn1—O4—C7 | 74.79 (15) | C8—Sn1—C7—O3 | 72.75 (14) |
O3—Sn1—O4—C7 | −0.92 (12) | O3i—Sn1—C7—O3 | 178.4 (2) |
O3i—Sn1—O4—C7 | 179.13 (12) | C7i—Sn1—C7—O3 | −179.12 (13) |
C7i—Sn1—O4—C7 | 179.50 (8) | O4i—Sn1—C7—O4 | −1.15 (19) |
C6—C1—C2—C3 | −0.3 (3) | C8i—Sn1—C7—O4 | 105.77 (15) |
C6—C1—C2—N1 | −179.19 (19) | C8—Sn1—C7—O4 | −108.89 (15) |
O1—N1—C2—C1 | −6.2 (3) | O3—Sn1—C7—O4 | 178.4 (2) |
O2—N1—C2—C1 | 172.2 (2) | O3i—Sn1—C7—O4 | −3.2 (4) |
O1—N1—C2—C3 | 175.0 (2) | C7i—Sn1—C7—O4 | −0.75 (12) |
O2—N1—C2—C3 | −6.7 (3) | O4—Sn1—C7—C6 | 10.8 (9) |
C1—C2—C3—C4 | 0.4 (3) | O4i—Sn1—C7—C6 | 9.6 (10) |
N1—C2—C3—C4 | 179.3 (2) | C8i—Sn1—C7—C6 | 116.5 (9) |
C2—C3—C4—C5 | −0.2 (3) | C8—Sn1—C7—C6 | −98.1 (9) |
C3—C4—C5—N2 | 179.9 (2) | O3—Sn1—C7—C6 | −170.9 (10) |
C3—C4—C5—C6 | 0.0 (3) | O3i—Sn1—C7—C6 | 7.5 (12) |
C2—C1—C6—C5 | 0.1 (3) | C7i—Sn1—C7—C6 | 10.0 (9) |
C2—C1—C6—C7 | 179.01 (19) | O4—Sn1—C8—C9 | −123.72 (17) |
N2—C5—C6—C1 | −179.8 (2) | O4i—Sn1—C8—C9 | 147.69 (17) |
C4—C5—C6—C1 | 0.1 (3) | C8i—Sn1—C8—C9 | 12.32 (16) |
N2—C5—C6—C7 | 1.3 (3) | O3—Sn1—C8—C9 | −69.62 (18) |
C4—C5—C6—C7 | −178.81 (19) | O3i—Sn1—C8—C9 | 92.85 (18) |
Sn1—O3—C7—O4 | −1.5 (2) | C7—Sn1—C8—C9 | −96.30 (18) |
Sn1—O3—C7—C6 | 178.28 (19) | C7i—Sn1—C8—C9 | 119.40 (18) |
Sn1—O4—C7—O3 | 1.7 (2) | Sn1—C8—C9—C10 | −72.8 (3) |
Sn1—O4—C7—C6 | −178.03 (16) | C8—C9—C10—C11 | −179.2 (3) |
C1—C6—C7—O3 | 176.9 (2) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O3 | 0.86 | 2.02 | 2.665 (3) | 132 |
C1—H1···O4 | 0.93 | 2.46 | 2.772 (3) | 100 |
N2—H2A···O2ii | 0.86 | 2.47 | 3.036 (3) | 124 |
N2—H2B···O1ii | 0.86 | 2.45 | 3.079 (3) | 130 |
Symmetry code: (ii) x, y+1, z. |
Experimental details
Crystal data |
Chemical formula | [Sn(C4H9)2(C7H5N2O4)2] |
Mr | 595.17 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 14.356 (4), 9.006 (2), 20.155 (5) |
β (°) | 106.305 (4) |
V (Å3) | 2501.0 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.48 × 0.44 × 0.18 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.626, 0.830 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6494, 2328, 2257 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.606 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.060, 1.14 |
No. of reflections | 2328 |
No. of parameters | 160 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.29 |
Selected geometric parameters (Å, º) topSn1—O4 | 2.1238 (15) | Sn1—O3 | 2.4665 (16) |
Sn1—C8 | 2.127 (2) | | |
| | | |
O4—Sn1—O4i | 85.68 (8) | C8i—Sn1—O3 | 89.31 (8) |
C8i—Sn1—C8 | 143.56 (14) | C8—Sn1—O3 | 84.95 (8) |
O4—Sn1—O3 | 56.37 (6) | O3—Sn1—O3i | 161.57 (7) |
O4i—Sn1—O3 | 142.05 (5) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O3 | 0.86 | 2.02 | 2.665 (3) | 132 |
N2—H2A···O2ii | 0.86 | 2.47 | 3.036 (3) | 124 |
N2—H2B···O1ii | 0.86 | 2.45 | 3.079 (3) | 130 |
Symmetry code: (ii) x, y+1, z. |
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The reaction of dibutyltin oxide with substituted aromatic carboxylic acids such as 3-hydroxyphthalide and (E)-3-(4-methoxyphenyl)-2-phenyl-2-propenoic acid leads to the formation of distannoxane-type complexes of [Sn4(C4H9)8(C8H5O3)4(µ-O)2] (Khoo & Hazell, 1999) and [Sn4(C4H9)8(C17H15O2)4O2] (Parvez et al., 2004), respectively. However, the reaction of dibutyltin oxide with 2-amino-5-nitrobenzoic acid gave a normal monomeric condensation reaction product, (I).
In (I), the molecule has a twofold symmetry (Fig. 1) and is isostructural with di-n-butylbis(thiophene-3-carboxylato-O,O')tin(IV), (II) (Yahyi et al., 2001). The ligands are chelated to atom Sn1 asymmetrically via both O atoms of the carboxylate groups in a bidentate manner. The geometry of the Sn atom is highly distorted octahedral (Table 1). The Sn—O bond lengths are in agreement with the isostructural analogue (II) [Sn—O = 2.1233 (13) and 2.5641 (14) Å]. The chelated aminobenzoate fragment Sn1/O3/O4/N1/C1–C7 is planar, with a maximum devation from the least squares plane of 0.029 (2) Å for atom O3. The molecules are stablized by intra- and intermolecular N—H···O hydrogen bonds (Table 2), forming one-dimensional chains parallel to the b axis (Fig. 2).