Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199013591/bk1497sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270199013591/bk1497Isup2.hkl |
CCDC reference: 142727
The title compound was prepared by treating equimolar quantities of phthaloylglycine and dibutyltin oxide in toluene/ethanol (3:1) under azeotropic reflux conditions for 4 h. The solid thus obtained was recrystallized from ethanol.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97.
[Sn4(C4H9)8(C10H6NO4)4O2] | Z = 1 |
Mr = 1780.28 | F(000) = 1800 |
Triclinic, P1 | Dx = 1.566 Mg m−3 |
a = 13.344 (5) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 14.393 (4) Å | Cell parameters from 25 reflections |
c = 11.683 (2) Å | θ = 9.0–15.0° |
α = 93.51 (3)° | µ = 1.38 mm−1 |
β = 110.00 (2)° | T = 170 K |
γ = 64.19 (2)° | Prism, colourless |
V = 1888.0 (10) Å3 | 0.48 × 0.26 × 0.21 mm |
Rigaku AFC-6S diffractometer | 5278 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.027 |
Graphite monochromator | θmax = 27.6°, θmin = 2.1° |
ω–2θ scans | h = 0→17 |
Absorption correction: ψ scans (north et al., 1968) ? | k = −16→18 |
Tmin = 0.70, Tmax = 0.75 | l = −15→14 |
9112 measured reflections | 3 standard reflections every 200 reflections |
8728 independent reflections | intensity decay: 1.1% |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0115P)2 + 2.325P] where P = (Fo2 + 2Fc2)/3 |
8728 reflections | (Δ/σ)max = 0.002 |
447 parameters | Δρmax = 0.93 e Å−3 |
2 restraints | Δρmin = −0.74 e Å−3 |
[Sn4(C4H9)8(C10H6NO4)4O2] | γ = 64.19 (2)° |
Mr = 1780.28 | V = 1888.0 (10) Å3 |
Triclinic, P1 | Z = 1 |
a = 13.344 (5) Å | Mo Kα radiation |
b = 14.393 (4) Å | µ = 1.38 mm−1 |
c = 11.683 (2) Å | T = 170 K |
α = 93.51 (3)° | 0.48 × 0.26 × 0.21 mm |
β = 110.00 (2)° |
Rigaku AFC-6S diffractometer | 5278 reflections with I > 2σ(I) |
Absorption correction: ψ scans (north et al., 1968) ? | Rint = 0.027 |
Tmin = 0.70, Tmax = 0.75 | 3 standard reflections every 200 reflections |
9112 measured reflections | intensity decay: 1.1% |
8728 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 2 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.93 e Å−3 |
8728 reflections | Δρmin = −0.74 e Å−3 |
447 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.94759 (3) | 0.05335 (2) | 0.35757 (3) | 0.02554 (8) | |
Sn2 | 0.91653 (3) | 0.24001 (2) | 0.58348 (3) | 0.02609 (8) | |
O1 | 0.9698 (2) | 0.0895 (2) | 0.5458 (2) | 0.0254 (6) | |
O2 | 0.9544 (3) | −0.0213 (3) | 0.1785 (3) | 0.0416 (9) | |
O3 | 0.9887 (3) | −0.1862 (2) | 0.2085 (3) | 0.0373 (8) | |
O4 | 1.0688 (3) | −0.2861 (3) | −0.0803 (3) | 0.0464 (9) | |
O5 | 0.7225 (3) | −0.1540 (3) | −0.0022 (4) | 0.0590 (11) | |
O6 | 0.8493 (3) | 0.2611 (2) | 0.3860 (3) | 0.0306 (7) | |
O7 | 0.7614 (3) | 0.4291 (2) | 0.4112 (3) | 0.0361 (8) | |
O8 | 0.4710 (3) | 0.4576 (3) | 0.1640 (4) | 0.0536 (10) | |
O9 | 0.7490 (3) | 0.5585 (3) | 0.1550 (3) | 0.0498 (10) | |
N1 | 0.8978 (4) | −0.1982 (3) | −0.0366 (3) | 0.0358 (9) | |
N2 | 0.6308 (3) | 0.4823 (3) | 0.1645 (3) | 0.0338 (9) | |
C1 | 0.9565 (4) | −0.1065 (4) | 0.1427 (4) | 0.0314 (11) | |
C2 | 0.9137 (5) | −0.1071 (4) | 0.0049 (4) | 0.0397 (12) | |
H2A | 0.8387 | −0.0461 | −0.0306 | 0.072 (3)* | |
H2B | 0.9707 | −0.1021 | −0.0254 | 0.072 (3)* | |
C3 | 0.9771 (4) | −0.2808 (4) | −0.0762 (4) | 0.0317 (11) | |
C4 | 0.9253 (4) | −0.3557 (4) | −0.1083 (4) | 0.0327 (10) | |
C5 | 0.9661 (4) | −0.4510 (4) | −0.1543 (4) | 0.0408 (12) | |
H5 | 1.0356 | −0.4774 | −0.1725 | 0.072 (3)* | |
C6 | 0.8987 (5) | −0.5045 (4) | −0.1719 (5) | 0.0481 (14) | |
H6 | 0.9243 | −0.5688 | −0.2019 | 0.072 (3)* | |
C7 | 0.7949 (5) | −0.4666 (4) | −0.1468 (5) | 0.0481 (14) | |
H7 | 0.7526 | −0.5057 | −0.1596 | 0.072 (3)* | |
C8 | 0.7533 (4) | −0.3709 (4) | −0.1024 (4) | 0.0418 (12) | |
H8 | 0.6830 | −0.3443 | −0.0859 | 0.072 (3)* | |
C9 | 0.8194 (4) | −0.3166 (4) | −0.0839 (4) | 0.0338 (11) | |
C10 | 0.8015 (4) | −0.2145 (4) | −0.0353 (4) | 0.0398 (12) | |
C11 | 1.0824 (4) | 0.0887 (3) | 0.3441 (4) | 0.0352 (11) | |
H11A | 1.0518 | 0.1304 | 0.2670 | 0.072 (3)* | |
H11B | 1.1003 | 0.1302 | 0.4094 | 0.072 (3)* | |
C12 | 1.1969 (4) | −0.0058 (4) | 0.3515 (5) | 0.0413 (12) | |
H12A | 1.1811 | −0.0436 | 0.2812 | 0.072 (3)* | |
H12B | 1.2237 | −0.0512 | 0.4246 | 0.072 (3)* | |
C13 | 1.2955 (5) | 0.0219 (5) | 0.3545 (6) | 0.0587 (16) | |
H13A | 1.2705 | 0.0641 | 0.2793 | 0.072 (3)* | |
H13B | 1.3085 | 0.0629 | 0.4221 | 0.072 (3)* | |
C14 | 1.4115 (6) | −0.0730 (5) | 0.3687 (7) | 0.083 (2) | |
H14A | 1.4714 | −0.0515 | 0.3734 | 0.072 (3)* | |
H14B | 1.4005 | −0.1117 | 0.2995 | 0.072 (3)* | |
H14C | 1.4361 | −0.1157 | 0.4423 | 0.072 (3)* | |
C15 | 0.7621 (4) | 0.0991 (4) | 0.2888 (4) | 0.0364 (11) | |
H15A | 0.7276 | 0.1437 | 0.3443 | 0.072 (3)* | |
H15B | 0.7281 | 0.1402 | 0.2105 | 0.072 (3)* | |
C16 | 0.7249 (5) | 0.0119 (4) | 0.2713 (5) | 0.0477 (14) | |
H16A | 0.7574 | −0.0290 | 0.3494 | 0.072 (3)* | |
H16B | 0.7589 | −0.0330 | 0.2157 | 0.072 (3)* | |
C17 | 0.5915 (5) | 0.0493 (5) | 0.2212 (6) | 0.0597 (17) | |
H17A | 0.5624 | 0.0833 | 0.1395 | 0.072 (3)* | |
H17B | 0.5773 | −0.0118 | 0.2121 | 0.072 (3)* | |
C18 | 0.5183 (8) | 0.1176 (8) | 0.2847 (10) | 0.068 (3) | 0.603 (7) |
H18A | 0.4379 | 0.1275 | 0.2445 | 0.072 (3)* | 0.603 (7) |
H18B | 0.5208 | 0.1833 | 0.2846 | 0.072 (3)* | 0.603 (7) |
H18C | 0.5470 | 0.0880 | 0.3676 | 0.072 (3)* | 0.603 (7) |
C18' | 0.5397 (13) | −0.0238 (10) | 0.1779 (15) | 0.068 (3) | 0.397 (7) |
H18D | 0.4547 | 0.0126 | 0.1541 | 0.072 (3)* | 0.397 (7) |
H18E | 0.5701 | −0.0776 | 0.2425 | 0.072 (3)* | 0.397 (7) |
H18F | 0.5604 | −0.0540 | 0.1088 | 0.072 (3)* | 0.397 (7) |
C19 | 0.7794 (4) | 0.3595 (3) | 0.3447 (4) | 0.0268 (9) | |
C20 | 0.7220 (4) | 0.3768 (3) | 0.2062 (4) | 0.0355 (11) | |
H20A | 0.7825 | 0.3620 | 0.1705 | 0.072 (3)* | |
H20B | 0.6871 | 0.3291 | 0.1783 | 0.072 (3)* | |
C21 | 0.5119 (4) | 0.5140 (4) | 0.1502 (4) | 0.0346 (11) | |
C22 | 0.4516 (4) | 0.6287 (4) | 0.1147 (4) | 0.0355 (11) | |
C23 | 0.3341 (5) | 0.6978 (4) | 0.0856 (5) | 0.0461 (13) | |
H23 | 0.2777 | 0.6768 | 0.0868 | 0.072 (3)* | |
C24 | 0.3033 (5) | 0.8003 (5) | 0.0543 (5) | 0.0569 (16) | |
H24 | 0.2245 | 0.8492 | 0.0349 | 0.072 (3)* | |
C25 | 0.3859 (5) | 0.8322 (4) | 0.0509 (5) | 0.0543 (16) | |
H25 | 0.3621 | 0.9018 | 0.0295 | 0.072 (3)* | |
C26 | 0.5048 (5) | 0.7612 (4) | 0.0793 (5) | 0.0506 (15) | |
H26 | 0.5611 | 0.7819 | 0.0767 | 0.072 (3)* | |
C27 | 0.5362 (4) | 0.6580 (4) | 0.1118 (4) | 0.0360 (11) | |
C28 | 0.6536 (4) | 0.5651 (4) | 0.1452 (4) | 0.0359 (11) | |
C29 | 0.7561 (4) | 0.2969 (4) | 0.6231 (4) | 0.0337 (11) | |
H29A | 0.7682 | 0.2492 | 0.6870 | 0.072 (3)* | |
H29B | 0.7434 | 0.3629 | 0.6563 | 0.072 (3)* | |
C30 | 0.6425 (4) | 0.3125 (4) | 0.5176 (4) | 0.0379 (12) | |
H30A | 0.6514 | 0.2458 | 0.4884 | 0.072 (3)* | |
H30B | 0.6321 | 0.3566 | 0.4508 | 0.072 (3)* | |
C31 | 0.5310 (4) | 0.3609 (4) | 0.5518 (5) | 0.0419 (12) | |
H31A | 0.5382 | 0.3145 | 0.6141 | 0.072 (3)* | |
H31B | 0.5244 | 0.4255 | 0.5862 | 0.072 (3)* | |
C32 | 0.4189 (5) | 0.3822 (5) | 0.4423 (5) | 0.0556 (16) | |
H32A | 0.3506 | 0.4179 | 0.4662 | 0.072 (3)* | |
H32B | 0.4212 | 0.3177 | 0.4133 | 0.072 (3)* | |
H32C | 0.4141 | 0.4244 | 0.3783 | 0.072 (3)* | |
C33 | 1.0537 (5) | 0.2873 (4) | 0.6139 (5) | 0.0411 (12) | |
H33A | 1.0491 | 0.3338 | 0.6776 | 0.072 (3)* | |
H33B | 1.1292 | 0.2261 | 0.6465 | 0.072 (3)* | |
C34 | 1.0572 (5) | 0.3400 (4) | 0.5082 (5) | 0.0499 (14) | |
H34A | 0.9838 | 0.4033 | 0.4766 | 0.072 (3)* | |
H34B | 1.0615 | 0.2948 | 0.4432 | 0.072 (3)* | |
C35 | 1.1615 (5) | 0.3667 (5) | 0.5433 (6) | 0.0598 (17) | |
H35A | 1.1541 | 0.4056 | 0.4735 | 0.072 (3)* | |
H35B | 1.1574 | 0.4113 | 0.6089 | 0.072 (3)* | |
C36 | 1.2790 (6) | 0.2758 (6) | 0.5833 (8) | 0.106 (3) | |
H36A | 1.3402 | 0.2987 | 0.6096 | 0.072 (3)* | |
H36B | 1.2873 | 0.2346 | 0.5163 | 0.072 (3)* | |
H36C | 1.2860 | 0.2348 | 0.6500 | 0.072 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02915 (19) | 0.02383 (18) | 0.01993 (16) | −0.00987 (14) | 0.00648 (14) | −0.00060 (12) |
Sn2 | 0.02808 (18) | 0.02088 (17) | 0.02653 (17) | −0.00905 (14) | 0.00917 (14) | −0.00513 (13) |
O1 | 0.0280 (16) | 0.0200 (15) | 0.0229 (15) | −0.0067 (13) | 0.0080 (13) | −0.0023 (12) |
O2 | 0.064 (2) | 0.036 (2) | 0.0293 (18) | −0.0248 (18) | 0.0191 (17) | −0.0125 (15) |
O3 | 0.047 (2) | 0.0347 (19) | 0.0232 (16) | −0.0166 (16) | 0.0056 (15) | −0.0023 (14) |
O4 | 0.042 (2) | 0.050 (2) | 0.056 (2) | −0.0230 (19) | 0.0264 (19) | −0.0170 (18) |
O5 | 0.039 (2) | 0.066 (3) | 0.058 (3) | −0.009 (2) | 0.023 (2) | −0.024 (2) |
O6 | 0.0332 (18) | 0.0251 (16) | 0.0260 (16) | −0.0077 (14) | 0.0081 (14) | 0.0006 (13) |
O7 | 0.043 (2) | 0.0253 (17) | 0.0365 (18) | −0.0120 (15) | 0.0145 (16) | −0.0034 (14) |
O8 | 0.048 (2) | 0.051 (2) | 0.063 (3) | −0.022 (2) | 0.019 (2) | −0.002 (2) |
O9 | 0.039 (2) | 0.050 (2) | 0.061 (3) | −0.0157 (18) | 0.0213 (19) | 0.0044 (19) |
N1 | 0.038 (2) | 0.037 (2) | 0.027 (2) | −0.0126 (19) | 0.0098 (18) | −0.0093 (17) |
N2 | 0.031 (2) | 0.030 (2) | 0.031 (2) | −0.0070 (18) | 0.0069 (18) | 0.0091 (17) |
C1 | 0.026 (2) | 0.042 (3) | 0.021 (2) | −0.012 (2) | 0.0071 (19) | −0.005 (2) |
C2 | 0.052 (3) | 0.032 (3) | 0.023 (2) | −0.014 (2) | 0.007 (2) | −0.005 (2) |
C3 | 0.036 (3) | 0.030 (3) | 0.023 (2) | −0.011 (2) | 0.009 (2) | −0.0037 (19) |
C4 | 0.033 (3) | 0.036 (3) | 0.027 (2) | −0.014 (2) | 0.010 (2) | −0.007 (2) |
C5 | 0.036 (3) | 0.038 (3) | 0.041 (3) | −0.011 (2) | 0.012 (2) | −0.010 (2) |
C6 | 0.057 (4) | 0.043 (3) | 0.047 (3) | −0.027 (3) | 0.018 (3) | −0.018 (3) |
C7 | 0.055 (4) | 0.049 (3) | 0.045 (3) | −0.031 (3) | 0.013 (3) | −0.008 (3) |
C8 | 0.029 (3) | 0.056 (3) | 0.035 (3) | −0.018 (3) | 0.006 (2) | −0.004 (2) |
C9 | 0.029 (3) | 0.039 (3) | 0.028 (2) | −0.011 (2) | 0.007 (2) | −0.003 (2) |
C10 | 0.033 (3) | 0.048 (3) | 0.025 (2) | −0.011 (2) | 0.005 (2) | −0.007 (2) |
C11 | 0.042 (3) | 0.027 (2) | 0.041 (3) | −0.016 (2) | 0.018 (2) | −0.002 (2) |
C12 | 0.042 (3) | 0.032 (3) | 0.055 (3) | −0.017 (2) | 0.023 (3) | −0.005 (2) |
C13 | 0.043 (3) | 0.058 (4) | 0.073 (4) | −0.017 (3) | 0.023 (3) | −0.001 (3) |
C14 | 0.056 (4) | 0.086 (6) | 0.109 (6) | −0.030 (4) | 0.033 (4) | −0.009 (5) |
C15 | 0.027 (2) | 0.038 (3) | 0.033 (3) | −0.009 (2) | 0.004 (2) | 0.000 (2) |
C16 | 0.036 (3) | 0.055 (4) | 0.053 (3) | −0.024 (3) | 0.014 (3) | −0.016 (3) |
C17 | 0.039 (3) | 0.078 (5) | 0.058 (4) | −0.030 (3) | 0.003 (3) | 0.011 (3) |
C18 | 0.039 (5) | 0.067 (6) | 0.087 (7) | −0.024 (5) | 0.012 (5) | −0.012 (5) |
C18' | 0.039 (5) | 0.067 (6) | 0.087 (7) | −0.024 (5) | 0.012 (5) | −0.012 (5) |
C19 | 0.027 (2) | 0.020 (2) | 0.031 (2) | −0.0077 (18) | 0.011 (2) | 0.0006 (18) |
C20 | 0.042 (3) | 0.026 (2) | 0.030 (2) | −0.007 (2) | 0.013 (2) | 0.0037 (19) |
C21 | 0.030 (3) | 0.039 (3) | 0.026 (2) | −0.009 (2) | 0.007 (2) | 0.001 (2) |
C22 | 0.033 (3) | 0.040 (3) | 0.024 (2) | −0.009 (2) | 0.007 (2) | 0.000 (2) |
C23 | 0.038 (3) | 0.050 (3) | 0.036 (3) | −0.010 (3) | 0.009 (2) | −0.003 (2) |
C24 | 0.039 (3) | 0.047 (4) | 0.050 (4) | 0.005 (3) | 0.008 (3) | −0.005 (3) |
C25 | 0.060 (4) | 0.030 (3) | 0.049 (3) | 0.000 (3) | 0.018 (3) | 0.004 (2) |
C26 | 0.059 (4) | 0.044 (3) | 0.043 (3) | −0.015 (3) | 0.021 (3) | −0.001 (3) |
C27 | 0.032 (3) | 0.034 (3) | 0.029 (2) | −0.006 (2) | 0.005 (2) | 0.003 (2) |
C28 | 0.035 (3) | 0.036 (3) | 0.032 (3) | −0.011 (2) | 0.011 (2) | 0.005 (2) |
C29 | 0.037 (3) | 0.033 (3) | 0.032 (3) | −0.013 (2) | 0.017 (2) | −0.007 (2) |
C30 | 0.033 (3) | 0.044 (3) | 0.035 (3) | −0.013 (2) | 0.015 (2) | −0.007 (2) |
C31 | 0.034 (3) | 0.045 (3) | 0.051 (3) | −0.017 (2) | 0.021 (3) | −0.011 (2) |
C32 | 0.036 (3) | 0.063 (4) | 0.061 (4) | −0.016 (3) | 0.016 (3) | 0.001 (3) |
C33 | 0.042 (3) | 0.043 (3) | 0.046 (3) | −0.027 (3) | 0.014 (2) | −0.009 (2) |
C34 | 0.054 (4) | 0.039 (3) | 0.064 (4) | −0.025 (3) | 0.021 (3) | −0.001 (3) |
C35 | 0.059 (4) | 0.057 (4) | 0.075 (4) | −0.039 (3) | 0.018 (3) | 0.001 (3) |
C36 | 0.059 (5) | 0.098 (7) | 0.170 (9) | −0.033 (5) | 0.049 (6) | 0.020 (6) |
Sn1—C11 | 2.125 (5) | C4—C5 | 1.388 (6) |
Sn1—C15 | 2.120 (5) | C4—C9 | 1.400 (6) |
Sn1—O1i | 2.043 (3) | C5—C6 | 1.380 (7) |
Sn1—O1 | 2.178 (3) | C6—C7 | 1.379 (7) |
Sn1—O2 | 2.304 (3) | C7—C8 | 1.385 (7) |
Sn1—O6 | 2.746 (3) | C8—C9 | 1.372 (7) |
Sn2—C33 | 2.133 (5) | C9—C10 | 1.491 (7) |
Sn2—C29 | 2.138 (4) | C11—C12 | 1.519 (6) |
Sn2—O1 | 2.037 (3) | C12—C13 | 1.521 (7) |
Sn2—O3i | 2.320 (3) | C13—C14 | 1.516 (8) |
Sn2—O6 | 2.157 (3) | C15—C16 | 1.518 (7) |
O1—Sn1i | 2.043 (3) | C16—C17 | 1.515 (7) |
O2—C1 | 1.263 (5) | C17—C18 | 1.428 (8) |
O3—C1 | 1.243 (5) | C17—C18' | 1.473 (9) |
O3—Sn2i | 2.320 (3) | C19—C20 | 1.517 (6) |
O4—C3 | 1.211 (5) | C21—C22 | 1.498 (7) |
O5—C10 | 1.208 (6) | C22—C23 | 1.372 (7) |
O6—C19 | 1.317 (5) | C22—C27 | 1.376 (7) |
O7—C19 | 1.220 (5) | C23—C24 | 1.383 (8) |
O8—C21 | 1.203 (6) | C24—C25 | 1.379 (8) |
O9—C28 | 1.200 (5) | C25—C26 | 1.393 (7) |
N1—C3 | 1.385 (6) | C26—C27 | 1.395 (7) |
N1—C10 | 1.409 (6) | C27—C28 | 1.489 (6) |
N1—C2 | 1.446 (6) | C29—C30 | 1.525 (6) |
N2—C21 | 1.397 (6) | C30—C31 | 1.527 (6) |
N2—C28 | 1.400 (6) | C31—C32 | 1.519 (7) |
N2—C20 | 1.450 (5) | C33—C34 | 1.513 (7) |
C1—C2 | 1.514 (6) | C34—C35 | 1.520 (7) |
C3—C4 | 1.483 (6) | C35—C36 | 1.475 (8) |
O1i—Sn1—C15 | 108.09 (15) | C9—C4—C3 | 109.0 (4) |
O1i—Sn1—C11 | 107.38 (15) | C6—C5—C4 | 116.7 (5) |
C15—Sn1—C11 | 143.71 (18) | C5—C6—C7 | 122.8 (5) |
O1i—Sn1—O1 | 76.73 (12) | C6—C7—C8 | 120.4 (5) |
C15—Sn1—O1 | 99.41 (15) | C9—C8—C7 | 117.6 (5) |
C11—Sn1—O1 | 95.88 (15) | C8—C9—C4 | 121.8 (5) |
O1i—Sn1—O2 | 91.03 (11) | C8—C9—C10 | 131.0 (5) |
C15—Sn1—O2 | 87.44 (16) | C4—C9—C10 | 107.1 (4) |
C11—Sn1—O2 | 84.49 (16) | O5—C10—N1 | 124.2 (5) |
O1—Sn1—O2 | 167.32 (11) | O5—C10—C9 | 130.0 (5) |
O1—Sn1—O6 | 65.00 (11) | N1—C10—C9 | 105.8 (4) |
O1i—Sn1—O6 | 141.54 (11) | C12—C11—Sn1 | 114.4 (3) |
O2—Sn1—O6 | 127.37 (12) | C11—C12—C13 | 113.0 (4) |
C11—Sn1—O6 | 81.08 (16) | C14—C13—C12 | 112.7 (5) |
C15—Sn1—O6 | 76.02 (16) | C16—C15—Sn1 | 116.1 (3) |
O1—Sn2—C33 | 111.46 (16) | C15—C16—C17 | 113.7 (5) |
O1—Sn2—C29 | 111.28 (15) | C18—C17—C18' | 103.7 (9) |
C33—Sn2—C29 | 135.34 (19) | C18—C17—C16 | 120.9 (6) |
O1—Sn2—O6 | 79.67 (11) | C18'—C17—C16 | 120.9 (8) |
C33—Sn2—O6 | 97.95 (16) | O7—C19—O6 | 123.4 (4) |
C29—Sn2—O6 | 101.78 (15) | O7—C19—C20 | 123.7 (4) |
O1—Sn2—O3i | 90.29 (11) | O6—C19—C20 | 113.0 (4) |
C33—Sn2—O3i | 82.44 (16) | N2—C20—C19 | 111.8 (4) |
C29—Sn2—O3i | 84.98 (15) | O8—C21—N2 | 125.0 (5) |
O6—Sn2—O3i | 169.40 (11) | O8—C21—C22 | 129.6 (5) |
Sn2—O1—Sn1i | 137.12 (14) | N2—C21—C22 | 105.4 (4) |
Sn2—O1—Sn1 | 119.55 (13) | C23—C22—C27 | 122.5 (5) |
Sn1i—O1—Sn1 | 103.27 (12) | C23—C22—C21 | 129.7 (5) |
C1—O2—Sn1 | 133.0 (3) | C27—C22—C21 | 107.8 (4) |
C1—O3—Sn2i | 135.1 (3) | C22—C23—C24 | 116.9 (5) |
C19—O6—Sn2 | 111.2 (3) | C25—C24—C23 | 122.0 (5) |
C3—N1—C10 | 112.3 (4) | C24—C25—C26 | 120.6 (5) |
C3—N1—C2 | 124.5 (4) | C25—C26—C27 | 117.5 (6) |
C10—N1—C2 | 123.1 (4) | C22—C27—C26 | 120.5 (5) |
C21—N2—C28 | 112.6 (4) | C22—C27—C28 | 109.3 (4) |
C21—N2—C20 | 123.3 (4) | C26—C27—C28 | 130.2 (5) |
C28—N2—C20 | 123.9 (4) | O9—C28—N2 | 125.4 (5) |
O3—C1—O2 | 126.6 (4) | O9—C28—C27 | 129.7 (5) |
O3—C1—C2 | 119.1 (4) | N2—C28—C27 | 104.9 (4) |
O2—C1—C2 | 114.3 (4) | C30—C29—Sn2 | 117.4 (3) |
N1—C2—C1 | 114.2 (4) | C29—C30—C31 | 113.8 (4) |
O4—C3—N1 | 124.2 (5) | C32—C31—C30 | 112.2 (4) |
O4—C3—C4 | 130.1 (4) | C34—C33—Sn2 | 119.4 (4) |
N1—C3—C4 | 105.7 (4) | C33—C34—C35 | 113.3 (5) |
C5—C4—C9 | 120.6 (5) | C36—C35—C34 | 114.2 (5) |
C5—C4—C3 | 130.5 (4) | ||
C33—Sn2—O1—Sn1i | 89.3 (3) | O1i—Sn1—C11—C12 | 26.2 (4) |
C29—Sn2—O1—Sn1i | −77.4 (3) | C15—Sn1—C11—C12 | −141.2 (4) |
O6—Sn2—O1—Sn1i | −176.1 (2) | O1—Sn1—C11—C12 | 104.1 (4) |
O3i—Sn2—O1—Sn1i | 7.3 (2) | O2—Sn1—C11—C12 | −63.1 (4) |
C33—Sn2—O1—Sn1 | −87.4 (2) | Sn1—C11—C12—C13 | −174.2 (4) |
C29—Sn2—O1—Sn1 | 105.90 (18) | C11—C12—C13—C14 | 176.9 (5) |
O6—Sn2—O1—Sn1 | 7.17 (14) | O1i—Sn1—C15—C16 | −25.2 (4) |
O3i—Sn2—O1—Sn1 | −169.38 (16) | C11—Sn1—C15—C16 | 142.2 (4) |
O1i—Sn1—O1—Sn2 | 177.7 (2) | O1—Sn1—C15—C16 | −104.2 (4) |
C15—Sn1—O1—Sn2 | −75.79 (19) | O2—Sn1—C15—C16 | 65.1 (4) |
C11—Sn1—O1—Sn2 | 71.18 (19) | Sn1—C15—C16—C17 | −179.6 (4) |
O2—Sn1—O1—Sn2 | 162.2 (5) | C15—C16—C17—C18 | −58.1 (9) |
O1i—Sn1—O1—Sn1i | 0.001 (1) | C15—C16—C17—C18' | 169.0 (9) |
C15—Sn1—O1—Sn1i | 106.52 (17) | Sn2—O6—C19—O7 | 3.7 (5) |
C11—Sn1—O1—Sn1i | −106.51 (16) | Sn2—O6—C19—C20 | −175.2 (3) |
O2—Sn1—O1—Sn1i | −15.5 (6) | C21—N2—C20—C19 | −88.9 (5) |
O1i—Sn1—O2—C1 | 27.4 (4) | C28—N2—C20—C19 | 84.9 (5) |
C15—Sn1—O2—C1 | −80.7 (4) | O7—C19—C20—N2 | −8.7 (7) |
C11—Sn1—O2—C1 | 134.8 (5) | O6—C19—C20—N2 | 170.3 (4) |
O1—Sn1—O2—C1 | 42.5 (8) | C28—N2—C21—O8 | −178.7 (5) |
O1—Sn2—O6—C19 | 170.2 (3) | C20—N2—C21—O8 | −4.3 (8) |
C33—Sn2—O6—C19 | −79.3 (3) | C28—N2—C21—C22 | 1.6 (5) |
C29—Sn2—O6—C19 | 60.4 (3) | C20—N2—C21—C22 | 176.1 (4) |
O3i—Sn2—O6—C19 | −170.7 (6) | O8—C21—C22—C23 | −2.1 (9) |
Sn2i—O3—C1—O2 | −10.4 (8) | N2—C21—C22—C23 | 177.5 (5) |
Sn2i—O3—C1—C2 | 170.1 (3) | O8—C21—C22—C27 | 179.6 (5) |
Sn1—O2—C1—O3 | −22.0 (8) | N2—C21—C22—C27 | −0.8 (5) |
Sn1—O2—C1—C2 | 157.5 (3) | C27—C22—C23—C24 | −1.0 (8) |
C3—N1—C2—C1 | −102.1 (5) | C21—C22—C23—C24 | −179.1 (5) |
C10—N1—C2—C1 | 74.7 (6) | C22—C23—C24—C25 | 0.7 (8) |
O3—C1—C2—N1 | 9.1 (7) | C23—C24—C25—C26 | 0.0 (9) |
O2—C1—C2—N1 | −170.5 (4) | C24—C25—C26—C27 | −0.5 (8) |
C10—N1—C3—O4 | −177.0 (5) | C23—C22—C27—C26 | 0.5 (8) |
C2—N1—C3—O4 | 0.1 (7) | C21—C22—C27—C26 | 179.0 (4) |
C10—N1—C3—C4 | 2.5 (5) | C23—C22—C27—C28 | −178.7 (4) |
C2—N1—C3—C4 | 179.5 (4) | C21—C22—C27—C28 | −0.2 (5) |
O4—C3—C4—C5 | −1.6 (9) | C25—C26—C27—C22 | 0.3 (8) |
N1—C3—C4—C5 | 179.0 (5) | C25—C26—C27—C28 | 179.2 (5) |
O4—C3—C4—C9 | 177.8 (5) | C21—N2—C28—O9 | 178.1 (5) |
N1—C3—C4—C9 | −1.6 (5) | C20—N2—C28—O9 | 3.6 (8) |
C9—C4—C5—C6 | −1.2 (7) | C21—N2—C28—C27 | −1.7 (5) |
C3—C4—C5—C6 | 178.2 (5) | C20—N2—C28—C27 | −176.2 (4) |
C4—C5—C6—C7 | 0.6 (8) | C22—C27—C28—O9 | −178.6 (5) |
C5—C6—C7—C8 | 0.3 (9) | C26—C27—C28—O9 | 2.3 (9) |
C6—C7—C8—C9 | −0.6 (8) | C22—C27—C28—N2 | 1.1 (5) |
C7—C8—C9—C4 | 0.0 (7) | C26—C27—C28—N2 | −177.9 (5) |
C7—C8—C9—C10 | −178.4 (5) | O1—Sn2—C29—C30 | −69.2 (4) |
C5—C4—C9—C8 | 1.0 (7) | C33—Sn2—C29—C30 | 128.5 (4) |
C3—C4—C9—C8 | −178.6 (4) | O6—Sn2—C29—C30 | 14.2 (4) |
C5—C4—C9—C10 | 179.7 (4) | O3i—Sn2—C29—C30 | −157.6 (4) |
C3—C4—C9—C10 | 0.2 (5) | Sn2—C29—C30—C31 | −175.6 (3) |
C3—N1—C10—O5 | 178.6 (5) | C29—C30—C31—C32 | 175.9 (4) |
C2—N1—C10—O5 | 1.5 (7) | O1—Sn2—C33—C34 | 93.7 (4) |
C3—N1—C10—C9 | −2.4 (5) | C29—Sn2—C33—C34 | −104.1 (4) |
C2—N1—C10—C9 | −179.5 (4) | O6—Sn2—C33—C34 | 11.7 (4) |
C8—C9—C10—O5 | −1.2 (9) | O3i—Sn2—C33—C34 | −179.0 (4) |
C4—C9—C10—O5 | −179.8 (5) | Sn2—C33—C34—C35 | −178.6 (4) |
C8—C9—C10—N1 | 179.8 (5) | C33—C34—C35—C36 | 63.5 (8) |
C4—C9—C10—N1 | 1.3 (5) |
Symmetry code: (i) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn4(C4H9)8(C10H6NO4)4O2] |
Mr | 1780.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 170 |
a, b, c (Å) | 13.344 (5), 14.393 (4), 11.683 (2) |
α, β, γ (°) | 93.51 (3), 110.00 (2), 64.19 (2) |
V (Å3) | 1888.0 (10) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 1.38 |
Crystal size (mm) | 0.48 × 0.26 × 0.21 |
Data collection | |
Diffractometer | Rigaku AFC-6S diffractometer |
Absorption correction | ψ scans (North et al., 1968) |
Tmin, Tmax | 0.70, 0.75 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9112, 8728, 5278 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.082, 1.02 |
No. of reflections | 8728 |
No. of parameters | 447 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.93, −0.74 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN, SHELXL97.
Sn1—C11 | 2.125 (5) | Sn2—C33 | 2.133 (5) |
Sn1—C15 | 2.120 (5) | Sn2—C29 | 2.138 (4) |
Sn1—O1i | 2.043 (3) | Sn2—O1 | 2.037 (3) |
Sn1—O1 | 2.178 (3) | Sn2—O3i | 2.320 (3) |
Sn1—O2 | 2.304 (3) | Sn2—O6 | 2.157 (3) |
O1i—Sn1—C15 | 108.09 (15) | O1—Sn2—C33 | 111.46 (16) |
O1i—Sn1—C11 | 107.38 (15) | O1—Sn2—C29 | 111.28 (15) |
C15—Sn1—C11 | 143.71 (18) | C33—Sn2—C29 | 135.34 (19) |
O1i—Sn1—O1 | 76.73 (12) | O1—Sn2—O6 | 79.67 (11) |
C15—Sn1—O1 | 99.41 (15) | C33—Sn2—O6 | 97.95 (16) |
C11—Sn1—O1 | 95.88 (15) | C29—Sn2—O6 | 101.78 (15) |
O1i—Sn1—O2 | 91.03 (11) | O1—Sn2—O3i | 90.29 (11) |
C15—Sn1—O2 | 87.44 (16) | C33—Sn2—O3i | 82.44 (16) |
C11—Sn1—O2 | 84.49 (16) | C29—Sn2—O3i | 84.98 (15) |
O1—Sn1—O2 | 167.32 (11) | O6—Sn2—O3i | 169.40 (11) |
Symmetry code: (i) −x+2, −y, −z+1. |
It has been reported that diorganotin complexes containing carboxylic acids, amino acids, purines, pyrimidines and peptides exhibit maximum antitumour activity, low mammalian toxicity and less nephrotoxicity than cis-platin (Sandhu et al., 1992; Danish et al., 1996; Gielen et al., 1992). The structural chemistry of organotin complexes of amino acids protected as carboxylates has afforded a great diversity of structural variation in recent years and complexes with a coordination number higher than four are being extensively studied (Tiekink, 1994; Mehring et al., 1998; Parvez et al., 1999). A number of crystal structures of organotin complexes containing the ligand N-phthaloylglycinate, a protected amino acid, and showing interesting features have been reported. For example, in triphenyltin N-phthaloylglycinate, six molecules were bridged via carboxylate groups to form a cyclic hexamer (Ng et al., 1990). In the tricyclohexyltin analog, the molecules were linked into a helical chain through an amido-O atom (Ng & Kumar Das, 1997). This protected amino acid, when condensed with (p-chlorophenyl)diphenyl hydroxide, yielded the corresponding aqua carboxylate, wherein the coordinated water molecules had linked adjacent molecules into sheets through hydrogen-bonding (Lo et al., 1997). It has been reported that dicarboxylato tetraorgano distannoxanes are often formed when diorganotin oxides are reacted with carboxylic acids and are the products of incomplete hydrolysis (Ng & Kumar Das, 1995a). In this paper we report the crystal structure of such a product, the title compound, (I).
The structure of (I) is presented in Fig. 1. It is composed of a centrosymmetric dimer, with Sn1/O1/Sn2/O6 and Sn1i/O1i/Sn2i/O6i rings flanking an Sn1/O1/Sn1i/O1i core ring on opposite sides (symmetry code: (i) 2 − x, −y, 1 − z). Similar structural units have already been reported (Ng, et al., 1991, 1994; Ng, 1998). The endocyclic Sn atoms of the Sn2O2 core are six-coordinate in a C2SnO4 skew-trapezoidal bipyramidal geometry, wherein Sn1 is coordinated to two bridging O atoms, two N-phthaloylglycinato anions and two α-C atoms of the n-butyl groups. The endocyclic Sn—O distances in the Sn2O2 core, 2.043 (3) and 2.178 (3) Å, are similar to the corresponding distances found in tetrabutyl bis(N,N-diethyl-thiocarbamoylthio) distannoxane dimer (Ng & Kumar Das, 1995a), bis[1,1,3,3-tetrabutyl-1,3-bis(picolinato N-oxide]distannoxane hydrate (Ng, 1998) and the isomeric triphenyltin 2-, 3- and 4-pyridinecarboxylate N-oxides (Ng & Kumar Das, 1995b). The exocyclic distances Sn1—O2 and Sn1—O6 comprise a strong and a relatively weak Sn···O interaction [2.304 (3) and 2.746 (3) Å, respectively] and are similar to those observed in the above mentioned complexes. The exocyclic Sn2 is essentially five-coordinate in a distorted trigonal geometry, the C—Sn—C angle being 135.34 (19)°.
The Sn—C distances, which are almost identical, lie within the narrow range of 2.120 (5)–2.138 (4) Å and are in agreement with the values reported for related structures. The molecular dimensions in the ligand, N-phthaloylglycinate, are normal and agree with the corresponding molecular dimensions reported in the structure of 2-phthalimidoethanoic acid monohydrate (Feeder & Jones, 1994).