J. Am. Chem. Soc., 996, 8(3), 3225-3232, DOI:0.02/ja9539756 Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machinereadable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html Copyright 996 American Chemical Society
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page I L Formula FW Spwo pup System irefections (*) 20r aa via CIA Pr Y VIA3 z F(000) DRIMg asl-3 Crystal size/fam.(mo-k.ya 4 6 C4HBiCtS3 C6HU BiAs 396.72 694.48 PnMu orthorxxaabic P2 k monoclinic (22) 37.04-42.25 (25).0-37.0 23 22 8.280(9) 8.875(4) 2.263(5) 7.582(2) 92529(9) 8.250(9) 90 90 90 96.05(4) 90 90 9223(6) 2832(3) 4 3 720 80 2.857 3.260 0.40x0.5xO.O 0.2x0.5x0.5 0.7069 0.7093 874.82 PI triclinic 25 (4.2-58.8) 23 9.757(2) 6.625(2) 37.942(3) 90=05(2) 07.84(3) 05.8() 74.9(6) 2 82 2.473 0.007x0.005x0.200.5478 (Ct Ka) C H 4 cn2s2 494.8 P2 monoclinic (2).58-29.03 9.590(3) 9.206(3) 9.76(2) 90 7.() 90 767.(4) 2 464 2.42 0.x0.Sx0. 30 0.7069 Scondary abs. max. actinction 0e4fndex ange of A, k. I Reflections 99.7 256.48 0.55 0.6764.0000 L000 4.708E-7 3.4665E-8 0,8;0,3;0,0 0,8;0,7;-8.8 786 342 364.7.s00 0.44"4.0000.9489E-6 0,0;-8,7;-,8 378 8.8.043.000 0,0;0,0;,-0,0 222 Unqeectices Nelections Paramstoned 786 493 (>3.00 C(I)) 47 unit 365 867 (I>3.00(I)) 94 a Weight 3479 3070 (>3m000)) 209 unit 47 05 (>2.00 0()) 62 (a. 0.0237) R Goodness of fit Mini max. features in fins differncema pfoa s Absolute structwe 0.0292 0.0334.222 +0.94-.37 0.035 0.035.9 +.3/-.08 0.045 0.056 4.26-4.02/2.8 0.090 0.0470.35 +0.740-0.597 0.03(2) Diffractonter Riaku AFC5R Emaf-Nonius CAN RigsD4 AF5R Riakn AFC5R *= F 2o)
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 2 2-chloro-, 3, 6-trithia-2-bismocane 4 Bil CIA C2A S2A Ci / S2/ C2 C* S2AX' CiAX C2A*
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 3 Table Fractional ic positional parameters and equivalent isotropic temperature factors (A2) for C 4 H 8 BiCIS 3 with e.s.d.s in parentheses. x y s Beq Bi() 0.02644(8) 0.7500 0.337(8) 4.70(2) Cl() 0.567(6) 0.7500 0.0450(5) 8.7(2) S() 0.0350(7) 0.7500 0.69(5) 6.6(2) 0.22(8) 0.5920(4) 0.3597(4) 7.6() C() 0.59(3) 0.636() 0.655(2) 7.2(6) 0.265(3) 0.59(2) 0.548(2) 9.(6) H() 0.2362 0.6583 0.7449 7.659 H(2) 0.0764 0.576 0.6868 7.659 H(3) 0.2799 0.5066 0.5772 0.9283 H(4) 0.3805 0.6334 0.5602 0.9283 Beq = X_2(UnI(aa-)2 + U 22 (bb) 2 + U 33 (b6) 2 + 2Ut 2 aa-bb* cosy + 2U 3 aa*cc" cos)8 + 2U 23 bb'cc' cos a) Table Anisotropic temperature factors (A2) for C 4 H 8 BiCIS 3 with e.s.d.s in parentheses. U U 22 U 33 U 2 U 3 U 23 Bi() 0.07(4) 0.36(0) 0.02(4) 0.0000 0.0008(3) 0.0000 Cl() 0.036(3) 0.94(8) 0.025(2) 0.0000 0.002(2) 0.0000 S() 0.045(3) 0.83(8) 0.02(2) 0.0000 0.005(2) 0.0000 0.88(6) 0.065(3) 0.038(2) 0.008(4) 0.005(3) 0.002(2) C() 0.7(2) 0.05() 0.05() -0.02() -0.02() 0.008(9) 0.2(2) 0.8(2) 0.05() 0.06(2) 0.03() 0.04() The general temperature factor expression: exp(-2r'(a" Uith + b' U 2 2 k 2 + c" 2 U 3? + 2a'b'U, 2 hk + 2a'c"U 3 hi + 2b'c'U 2 3 ki))
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 4 Table :Interic distances (A) for C 4 H 8 BiCIS 3. -3 Bi() Bi() S() Cl() C() distance 2.682(5) 2.54(6).75(2).78(2) Bi() Bi() S() C() S() C() distance 2.849(5) 2.54(6).75(2).42(2) Table :Interic distances (A) for C4H 8 BiCIS 3. distance distance C() H().08 C() H(2).08 H(3).08 H(4).08 Table :Intramolecular bond angles (degrees) involving non-hydrogen s for C 4 H 8 BiCIS 3. angle angle Cl() Bi() S() 55.3(2) Cl() Bi() 85.2() Cl() Bi() 85.2() s() Bi() 79.0() S() Bi() 79.0() Bi() 99.4(3) Bi() S() C() 0.T(6) Bi() S() C() 0.7(6) C() S() C() 05() Bi() 07.5(8) S() C() 2() C() 23() 0
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 5 Table :Intramolecular bond angles (degrees) involving non-hydrogen s for C4H 8 BiCIS 3. S() H() C() C() C() C() H() H() H(2) H(4) H(4) angle 06.3 06.3 09.5 05.7 05.7 S( ) C() H(3) C() C() H(2) H(2) H(3) H(3) H(4) angle 06.3 06.3 05.8 05.8 09.5 Table :Special contacts (A) involving non-hydrogen s for C4H 8 BiCIS 3. distance ADC distance ADC Bi() Cl( ) 3.288(5) 48502 Bi() 3.5(6) 46502 Bi() 3.5(6) 45508 Cl() S() 3.430(7) 56502 CI() 3.83(2) 46502 Cl() 3.83(2) 45508 Cl() C() 3.87(2) 5540 Cl() C() 3.87(2) 56407 S() C() 3.96(2) 46802 S() C() 3.96(2) 45808 C() 3.52(2) 56404 3.66(2) 56404 Bi() 2.54(6) Bi() 2.54(6) 56507 Bi() Cl() 2.682(5) Bi() S( ) 2.849(5) Bi() Cl() 3.286(5) 46502 Bi() 3.5(2) Bi() 3.5(2) 56507 Bi() 3.5(6) 48502 Bi() 3.5(6) 45508 Bi() C() 3.63(2) Bi() C() 3.63(2) 56507 3
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 6 J& - 3 :L -4-v, 2-bis (2- (, 3-dithia-2-bismolane) thio) ethane 6 C3 C4 SIO* S3 / / C2 S2 SIO* CI Si i /' S5 S6 C5 C6 S7*
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 7 Table :Fractional ic positional parameters and equivalent isotropic temperature factors (A2) for C 6 H 2 Bi 2 S 6 with e.s.d.s in parentheses. Bi() Bi(3) Bi(4) S() S(0) S() C() x 0.668() 0.989() 0.453() -0.373() 0.6278(7) 0.8686(7) 0.455(7) 0.3767(8) 0.3649(7) 0.46(8) 0.04(7) 0.350(7) -0.0768(7) -0.20(8) -0.565(7) -0.3799(8) 0.750(3) 0.782(3) 0.483(3) 0.39(4) 0.357(3) 0.207(3) 0.223(2) 0.257(3) y 0.07384(6) 0.2723(5) 0.0470(6) 0.5778(5) -0.0726(4) 0.045(4) 0.0675(4) 0.3(4) 0.0450(4) 0.202(4) -0.0404(4) 0.067(4) 0.0957(4) 0.2672(3) 0.0736(4) 0.2307(4) -0.02() -0.046() 0.57(2) 0.223(2) 0.095() 0.28(2) -0.076() -0.02(2) z -0.9020(6) -0.293(6) -0.6878(6) -0.72885(6) -0.98(4) -0.0859(4) -0.0989(4) -0.779(4) -0.299(3) -0.3448(4) -0.6982(4) -0.5870(4) -0.6007(4) -0.6888(4) -0.8040(4) -0.8490(4) -0.7() -0.06() -0.054() -0.079(2) -0.382() -0.408(2) -0.620() -0.557(l) e,3.79(3).70(3).62(3).89(3).8(2) 2.3(2) 2.0(2) 2.7(2).8(2) 2.9(2) 2.0(2) 2.5(2) 2.2(2) 2.(2).8(2) 3.2(2) 2.2(5) 2.9(6) 3.0(6) 4.4(7) 2.7(6) 3.3(6).(5) 3.(6) 8
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 8 x y z B, -0.07(4) 0.87(2) -0.554(2) 5.9(8) C(0) -0.074(5) 0.25(2) -0.593(2) 7.8(8) C() -0.202(3) 0.3(2) -0.896(2) 3.8(6) -0.2(3) 0.96() -0.896() 3.0(6) H() 0.7038-0.440-0.0957 2.5777 H (2) 0.8443-0.73-0.326 2.5777 H (3) 0.8484-0.0690-0.0225 3.4823 H(4) 0.6892-0.0338-0.0422 3.4823 H(5) 0.4683 0.497-0.0035 3.6375 H(6) 0.5853 0.708-0.0575 3.6375 H(7) 0.4346 0.2672-0.054 5.3202 H(8) 0.298 0.258-0.0653 5.3202 H(9) 0.428 0.355-0.3762 3.295 H(0) 0.3832 0.062-0.49 3.295 H() 0.337 0.0888-0.47 3.8702 H(2) 0.225 0.509-0.4546 3.8702 H(3) 0.748-0.94-0.603.3709 H(4) 0.36-0.090-0.6365.3709 H(5) 0.3228-0.0453-0.596 3.764 H(6) 0.654-0.0077-0.5383 3.764 H(7) -0.522 0.874-0.56 6.789 H(8) 0.0228 0.885-0.5232 6.789 H(9) 0.080 0.2735-0.5823 8.579 H(20) -0.527 0.280-0.5720 8.579 9
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 9 x y z Beq H(2) -0.204 0.02-0.95 4.4560 H(22) -0.296 0.0898-0.983 4.4560 H(23) -0.0 0.223-0.9458 3.686 H() -0.340 0.286-0.8732 3.686 Beq = x--(uit(aa') 2 + U 22 (bb*) 2 + U 33 (bb*) 2 + 2Ul 2 aa'bb' cos y + 2Ut 3 aa'cc' cosl3 + 2U 23 bbcc* cos a) 0
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 0 I Table :Interic distances (A) for C 6 Hl 2 Bi 2 S 6. 3 3 - / 4 distance distance Bi() S() 2.59(6) Bi() 2.565(6) Bi() 2.634(7) 2.635(7) 2.552(6) 2.553(7) Bi(3) 2.580(7) Bi(3) 2.540(6) Bi(3) Bi(4) S() 2.665(7) 2.554(7) Bi(4) Bi(4) S(0) 2.643(6) 2.550(7) S() C().82(2).8(3) C (3).79(3).83(3).75(3).85(3).8(2).87(3).8(4) S(0) C(0).78(4) S() C().83(3).8(3) C().42(3).46(4).48(3).50(3) C(0).34(5) C().47(3) 2
(0996 American Chemical Society J. Am. Chem. Soc. VI 8 Page3225 Agocs Supplemental Page distance distance C() H() C( ) H(2) H(3) H(4) H(S) H(6) H(7) H(8) H(9) H(0) H() H(2) H(3) H(4) C(S) H(5) C(s) H(6) H(7) 0.94 H(8) C(0) H(9) 0.9 C(0) H(20) 0.98 C() H(2) C() H(22) H(23) H() 3
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 2 3 B 8 a 3t Bi BI 52 B2 B2 82 B2 B2 Bn2 Table :Special contacts (A) S2 SI S3 S7 S5 S0 s5 S6 S3 S7 50 $ distance 2.565(7) 2.59(7) 2.633(7) 3.34(7) 3.70(6) 3.39(l) 3.902 (" 2.552(7) 2.553(7) 2.637(7) 3.(7) 3.257(6) 3.52(9) 3.590(9) i3 involving non-hydrogen s for Q I 2 Bi 2 S 6. ADC(*) 3. 65403 65504. 2. 55403 4 55403 B3 B3 g3 33 53 53 B3 4 84 B4 B4 B4 B4 so S7 S9 SI S SO S2 Sl S0 S9 S S5 distance 2.539(7) 2 58(7) 2 664() 3.099(7) 3.28(9) 3.389(7) 3.7043(9) 2.549() 2.553() 2.6445(9) 3.77(9) 3.292(6) 3.453(7) 3.628(7) ADC(*) 64 65403 55404 55403 45404 55403 Contacts out to 4.9 angstroms. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 3 Table :Intramolecular bond angles (degrees) involving non-hydrogen s for C 6 H 2 Bi 2-2S 6. S() S(0) Bi() Bi() Bi(3) Bi(3) Bi(4) S() Bi() Bi() Bi(3) Bi(3) Bi(4) S() S() C() C() C() C(0) angle 83.7(2) 9.2(2) 86.4(2) 83.5(2) 94.2(2) 87.(2) 00.4(8) 99.6(9) 0.6(9) 02.2(7) 04() 0.(9) 6() 20(2) 5() 5() 9(3) S() C() 3() S() S(0) S() Bi() Bi(3) Bi(4) Bi(4) S(0) Bi() Bi(3) Bi(4) Bi(4) S(0) C(0) S() C (4) C(0) C() C() angle 84.7(2) 04.0(2) 84.3(2) 82.6(2) 00.3(2) 85.0(2) 95.2(8) 99() 97.6(9) 96.9(8) 03() 97.5(9) 7() 4(2) 3() () 30(3) 6() 4
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 4 Table :Special angles (degrees) involving non-hydrogen s for CHI 2 Bi 2 S 6. S2 B S2 8 52 Bril S2 B S2 8l S2 8 S 8l SI. l SI BI Si li Si a S3 all S3 all S3 a S3 Bil 87 Bl S7 al S7 all $5 SI i S5 B S0 ar 55 B2 85 B2 S5 2 S5 B2 85 s2 angle angle Sl S3 S7 S5 S0 S3 S7 S5 SO S7 S5 50 S5 S0 $0 84 S6 S3 S7 50 83.8(2) 9.2(2) 87.9(2) 55.9(2) 79.3(2) 22.8(2) 84.7(2) 82.0(2) 73.9(2) 5.6() 32.7(2) 66.6(2) 78.0(2) 8.(2) 59.2(2) 97.7(2) 74.9() 3.5(2).8() 69.8(2) 75.6() 84.3(2) 04.(2) 78.3(2) 90.0(2) 57.3() S5 S6 S6 S6 S6 S6 54 S3 S3 S3 S7 S7 50 S8 S8 s$ s5 S8 Se $7 87 57 87 82 B2 82 B2 B2 B2 B2 B2 B2 2 32 82 82 B2 B2 B2 33 B3 53 BI3 B3 B3 33 B3 B3 3 5 S3 87 S0 sli S3 S7 50 S $7 80 8 S0 Sl Si S7 89 S Sl 80 S9 S Si 66.3(2) 86.4(2) 46.3(2) 78.7(2) 79.(2) 28.2(2) 70.5(2) 58.5(2) 90.4(2) 40.0(2) 29.3(2) 23.7() 69.5() 7.7() 60.7() 3.03(3) 83.6(2) 94.4(2) 88.3(2) 54.2(2) 77.5(2) 27.9(2) 83.2(2) 82.8(2) 7.4() 5.3(2) Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 5 J3)?2, -)- /65 $7 S9 S9 S9 S9 S S Sl S Si S2 S2 82 S2 S2 S2 Si Si Si 5 80 S0 80 80 angle B3 3 B3 B3 B3 B33 B3 B3 83 S3 33 BI4 84 84 B4 84 B4 Bi4 84 B4 BI4 BI4 B4 B4 B4 84 S0 S Si S0 Si S0 SIO SIO Si 50 S9 S S3 S0 89 S S5 59 Si S5 3.9() 65.4() 76.84 (2) 9.3() 6.77(2) 94.6() 75.4(2) 26.6() 28.0() 69.39(2) 76.6() 84.95(3) 87.5(3) 50.34(4) 77.5() 82.4() 26.57(9) 00.33(3) 80.34(2) 90.7() 60.5() 65.6() 70.52(2) 60.3() 93.9() 39.2() S9 S9 S9 S 84 B4 a4 84 34 B4 84 Sl 28.0() angle 7.4(l) S5 69.44(9) 72.(2) S5 60.4(2) SS.0(2) Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 6 3) 3w /b Table :Anisotropic temperature factors (A2) for C 6 H 2 Bi 2 S 6 with e.s.d.s in parentheses. Bi() Bi(3) Bi(4) S() S(0) S() U 0.023(6) 0.069(6) 0.099(6) 0.074(6) 0.022(4) 0.0(4) 0.030(4) 0.022(4) 0.026(4) 0.04(4) 0.020(4) 0.027(4) 0.026(4) 0.026(4) 0.02(4) 0.04(5) U 2 2 0.0226(7) 0.092(7) 0.094(7) 0.0207(7) 0.02(4) 0.032(5) 0.025(4) 0.025(5) 0.023(4) 0.030(5) 0.025(5) 0.035(5) 0.025(4) 0.02(4) 0.0(5) 0.028(5) U 33 0.0239(7) 0.028(7) 0.0226(7) 0.0338(7) 0.026(4) 0.029(4) 0.022(4) 0.055(6) 0.09(4) 0.037(5) 0.032(4) 0.029(5) 0.036(5) 0.040(5) 0.023(4) 0.053(5) Ut 2 0.0006(5) -0.002(5) 0.00(5) -0.0007(5) -0.004(3) -0.002(3) 0.003(3) -0.005(3) 0.002(3) 0.008(4) -0.003(3) 0.005(3) 0.00(3) -0.006(3) 0.002(3) 0.005(4) U 3 0.0022(5) 0.006(5) 0.0042(5) 0.0030(5) -0.00(3) -0.003(3) 0.005(3) -0.005(4) 0.002(3) -0.008(4) -0.002(3) -0.009(3) 0.03(3) -0.003(3) -0.002(3) -0.00(4) U 23-0.0008(5) -0.0020(5) 0.00(5) -0.0023(5) 0.00(3) -0.006(3) 0.004(3) -0.0(4) -0.003(3) 0.02(4) 0.00(3) 0.005(3) 0.008(3) -0.003(3) 0.006(3) 0.022(4) The general temperature factor expression: exp(-27r2(a' 2 Ujh 2 + b 2 U 22 k 2 + c' 2 U 3 3l 2 + 2a*b*U 2 hk + 2a'c'Ul 3 hl + 2b'c'U 2 3kI))
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 7 bis(2-(, 3, 6-trithia-2-bismocane)thio)ethyl sulfide 9. S8* S5 C7 S9* * C8 Bi2* S6* C6 S5* C5 vi- S9 S 4 Bi2 C 2 SB CiI - Ci0C S3* S3*x C9 S2 Bi SI* S2x BiS7 Si S7sI* S7x ( S7* C4 Bi IM S7* C2 S3 C3
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 8 Table : Fractional ic positional parameters and equivalent isotropic temperature factors ( ) for CI 2 H B 2 S 9 with e.s.d.s in parentheses. x Y z Bq Bi() 0.9226(7) 0.44786(4) 0.23237(9) 2.3(2) 0.8664(6) 0.90663(4) 0.75306(9).93() s() 0.7870(5) 0.4870(3) -0.0793(6) 2.92(0) 0.6726(5) 0.3863(3) 0.2940(7) 3.3() 0.7849(5) 0.2802(3) -0.0009(7) 3.3() 0.665(4) 0.8776(3) 0.4988(6) 2.70(9) 0.8923(5).0732(3) 0.5495(7) 3.() 0.8008(5).09(3) 0.936(6) 2.7(9) 0.965(5) 0.600(3) 0.3607(6) 2.8(9) 0.8825(5) 0.7296(3) 0.685(6) 2.86(0) 0.7523(5) 0.8030(3) 0.9470(7) 3.() C() 0.635(2) 0.393() -0.78(3) 3.8(5) 0.683(2) 0.36() -0.200(3) 3.4(4) 0.643(2) 0.237() 0.05(3) 3.9(5) 0.673(2) 0.277() 0.283(3) 3.9(5) 0.682(2) 0.935() 0.327(3) 3.4(5) 0.7(2).030() 0.36(2) 3.(4) 0.823(2).29() 0.684(3) 3.(4) ((8) 0.78(2).074() 0.770(2) 2.4(4) 0(9) 0.778(2) 0.6() 0.327(3) 2.7(4) C(0) 0.790(2) 0.70() 0.386(2) 2.6(4) (() 0.728(3) 0.674() 0.698(3) 4.0(5) ((2) 0.767(3) 0.700() 0.895(3) 4.(5) () 0.5692 0.3800-0.088 4.0998 9
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 9 J) 3o -/ x y z B, H(2) 0.5772 0.4032-0.2954 4.0998 H(3) 0.7487 0.33-0.272 3.5857 H(4) 0.598 0.2728-0.263 3.5857 H(5) 0.5492 0.45 0.030 4.2676 H(6) 0.6309 0.785 0.098 4.2676 H(7) 0.7686 0.274 0.3570 4.077 H(8) 0.5980 0.35 0.3329 4.077 H(9) 0.769 0.9203 0.322 3.8644 H(0) 0.6047 0.962 0.2 3.8644 H() 0.6387.0436 0.3840 3.4868 H(2) 0.7340.0554 0.2565 3.4868 H(3) 0.9092.647 0.7770 3.876 H(4) 0.7743.663 0.6 3.876 H(5) 0.6388.0369 0.6774 2.604 H(6) 0.6765.088 0.8236 2.604 H(7) 0.772 0.5976 0.2045 3.0607 H(8) 0.7278 0.5738 0.3960 3.0607 H(9) 0.6942 0.7094 0.3538 2.8400 H(20) 0.8488 0.7380 0.3222 2.8400 H(2) 0.637 0.6863 0.6307 4.459 H(22) 0.703 0.639 0.6779 4.459 H(23) 0.865 0.6972 47 4.649 H() 0.6979 0.6589 0.944 4.649 B,.q = r (U (aa') + U2 bbo ) + U.;a(cc') + 2Ut 2 aa'bb cos- + 2U 3 aa'cc" cos3 + 2U 2.3bb'cc' cosa) 0
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 20 Table : Anisotropic temperature factors (A' ) for C, 2 H, 4 Bi 2 S 9 with e.s.d.s in parentheses. U U054 U.3 Bi() 0.0(3) 0.0235(4) 0.0396(4) 0.0004(2) 0.0050(3) -0.0043(3) 0.0094(3) 0.0228(4) 0.0343(4) 0.0022(2) -0.0006(3) -0.0028(3) S() 0.026(2) 0.03(2) 0.046(3) 0.003(2) 0.005(2) 0.002(2) 0.09(2) 0.044(3) 0.063(3) 0.003(2) 0.08(2) 0.00(2) 0.029(2) 0.027(2) 0.06(3) 0.003(2) 0.008(2) -0.02(2) 0.02(2) 0.035(2) 0.040(3) 0.00(2) -0.008(2) -0.007(2) 0.025(2) 0.033(2) 0.058(3) 0.00(2) 0.09(2) 0.003(2) 0.028(2) 0.035(2) 0.035(2) 0.00(2) 0.002(2) -0.006(2) 0.08(2) 0.029(2) 0.05(3) 0.003(2) 0.003(2) -0.009(2) 0.029(2) 0.029(2) 0.047(3) 0.02(2) 0.004(2) -0.005(2) 0.034(2) 0.036(2) 0.048(3) 0.008(2) 0.07(2) 0.004(2) C() 0.005(8) 0.05() 0.06() -0.02(8) -0.0(8) 0.0() 0.03() 0.04() 0.05() -0.06(8) 0.00(9) -0.05(9) 0.04() 0.04() 0.07(2) -0.003(9) 0.02() 0.0() 0.03() 0.05() 0.06() -0.007(9) 0.020(0) 0.0() 0.04() 0.05() 0.04() 0.05(9) 0.007(9) -0.00(9) 0.04() 0.06() 0.03() 0.020(0) 0.02(9) 0.00(9) 0.04() 0.028(0) 0.05() 0.0(8) 0.009(9) -0.002(8) 0.020(9) 0.04() 0.03() 0.04(8) 0.006(7) -0.007(8) 0.02(8) 0.04() 0.05() 0.00(7) 0.003(8) -0.003(8) C(0) 0.0(9) 0.034(0) 0.04() 0.03(8) 0.005(8) 0.006(8) C() 0.06() 0.0(0) 0.06() 0.00(0) 0.02() 0.000(9) 0.06() 0.04() 0.05() 0.0() 0.0() 0.0() The general temperature factor expression: exp(-2r 2 (a'"ul Ikh + b 2 U 22 k 2 + c 2 U33 2 + 2a'b'Ul 2 hk + 2a'c'U] 3 hi + 2b'c'U 23 kl))
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 2 Table Intic distances (A) for C 2 IL 4 Bi 2 S 9. distance distance Bi() S() 2.597(5) Bi() 2.659(4) Bi() 2.65(4) 2.567(4) 2.599(4) 2.566(5) S() C().8(2).83(2).79(2).82(2).84(2).82(2).80(2) C(s).8(2).8(2) C(0).79(2) C().83(2).8(2) C().5(3).48(3).52(3).5(3) C(0).53(2) C().53(3) 4
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 22 distance distance C() H() C() H(2) 0.97 H(3) 0.96 H(4) 0.93 H(5) 0.96 H(6) 0.96 H(7) 0.96 H(8) 0.98 H(9) H(0) 0.96 H() 0.99 H(2) H(3) 0.97 H(4) 0.96 H(5) H(6) H(7) 0.96 H(8) 0.96 C(0) H(9) C(0) H(20) 0.97 C() H(2) 0.97 C() H(22) 0.96 H(23) H() 0.98 5
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 23 Table : Intramolecular bond angles (degrees) involving non-hydrogen s for C 2H., 4 Bi 2 S 9. angle angle S() Bi() 92.4(2) S() Bi( ) S( 7) 88.8(2) Bi() 95.6(2) 93.9() 93.5(2) 8.7(2) Bi() S() C() 04.0(7) Bi() 96.6(6) 03.7(0) 00.(6) 0.4(9) 03.3(6) Bi() 04.8(6) C(0) C() 98.3(9) 08.8(8) S() C() 4() C() 6() 5() 5() 3() 3() 4() 5() C(0) 09() C(0) 3() C() 09() C() 5() 6
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 3)?~ S() H() C() H(5) H(9) H(3) c(0) H(7) C() C() C() H() H() H(2) H(4) H(4) H(5) H(3) H(6) H(8) H(8) H(9) (9) H(0) H(2) H(2) H(3) H(3) H(4) H(6) H(6) H(7) H(7) H(8) angle 0.6 07.3 08.0 09. 08.3 07.7 07.8 08.0 08.9 07.7 09. 07.9 08.0 0.5 0.3 08. 08.3 06.8 08.5 08.6.6 09.2 07.7 C(0) H(20) 08.0 S( ) C() H(3) H(7) H() H(5) c(0) C() C() c(9) C(0) H(2) H(2) H(3) H(3) H(4) H(6) H(6) H(7) H(7) H(8) H(0) H(0) H() H() H(2) H(4) H(4) H(5) H(5) H(6) H(8) H(8) H(9) C(0) H(9) 0.4 7 angle 09.2 06.7 07.5 05.7 09.7 08.0 09.8 0.0 08.0 06.3 08.4 09.5 08.6 07.7 06.3 09.0 09.6 08.2 06.9 09.0.3 07.8 09.3
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 25 angle angle C(0) H(20) 07. H(9) C(0) H(20) 07.9 C() H(2) 09.5 C() H(22) 09.9 C() H(2) 09.8 C() H(22).0 H(2) C() H(22) 06.9 H(23) 09.6 H() 07.9 C() H(23) 08.2 C() H() 07.6 H(23) H() 07.4 8
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 26 Table : Special contacts (A) involving non-hydrogen s for C 2 H Bi 2 S,. distance ADC(*) distance ADC (*) Bi () S() 2.597(5) 2.82(2) Bi () S() 3.346(5) 76502 2.80(2) Bi() 2.559(4).82 (2) Bi() 3.07(5).80(2) Bi() 2.65(4) 2.80(2) Bi () 3.26(5) 76602 3.380(6) Bi() C() 3.5(2) 2.8t2) Bi () 3.3(2).8(2) Bi (2) 2.567(4) 3.369(6) Bi (2) 3.97(5).8(2) 2.599(4) C(0) 2.73 (2) 3.342(4) 77702 2.79(2) S() S() S() C() C (3) C() C (2) 3.92(4) 2.566(5) 3.4(2) 3.49(2) 3.490(7).8(2) 2.80(2) 2.79(2).83(2) 2.8(2).79(2).82(2) 2.78(2).84(2) C() C() C(0) C() C() C(0).79(2).83(2) 2.75(2) 2.83(2).8(2).5(3) 3.44(3) 2.84(3).46(3).52(3) 2.80(3) 3.36(3).5(3).53(2) Distances are in angstroms. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 27 atcm distance C() 3.34(3) C(0) C() 2.74(3) C().53(3) ADC%*) distance J ADC (*) Distances are in angstroms. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 28. Table : Special angles (degrees) involving non-hydrogen s for C, H 2 4 Bi 2 S,. S() S( ) S() S() S( ) S( ) S() S() S() S() S() S() S() angle angle Bi() S() 79.8() Bi() 70.9(4) Bi() 92. 4 (2) C () Bi(l) 74.(5) Bi() 75.5() 74.9() Bi() 88.8(2) 93.9() Bi() 69.7() 67.4() Bi() C() 30.0(3) 86.() Bi() 03.(4) 93.5(2) Bi() 70.0() 32.(4) Bi() 94.9() 7.9(3) Bi() 90.6() 74.2() Bi() 0.2() 92.9() Bi() C() 98.(4) 27.0( Bi() 42.5(4) 52.3( Bi() 76.9() 50.0(4) Bi() 95.6(2) 49.2(3) Bi() 78.0() 79.4() Bi() C() 72.3(4) 57.6( Bi() 33.3 (4) 8.7(2) Bi() 62.() 02.3(] Bi() 05.6() 30.3(3) Bi() C() 50.(4) 04.(' Bi() 5.5(4) 96.0(: Bi() 88.3() 38.8(, Bi() C() 2.2(4) 97.8(3 Bi() 26.6(4) 75.9( Bi() C() 45.0(3) 89.6(3 Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses. J 3=2 3j
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 29 Bi () Bi () Bi () Bi () Bi () Bi() Bi () C() Bi() Bi () Bi() Bi() Bi() Bi() Bi() S() S() S() S() Bi (2) S() S() S() S() S() S( ) S() S() S() S() Bi() C() C() C() S() C() C() angle 58.0(3) 25.(4) 03.5(3) 72.6(4) 00.2() 58.4() 04.0(7) 89.0(5) 02.0() 2.8(8) 0.2(4) 53.3(7) 30.7(4) 29.4(8) 87.8(4) 96.6(6) 28.2(8) 46.() 73.0(4) 98.8(6) 95.3(7) 68.7(4) 3.0(4) 52.9(6) 08.0(7) 95.0(5) C() C () C() Bi (2) angle 28.8(8) 93.2(8) 94.5(7) 04() 6.4(8) 28.4(8) 00.(6) 90.7(4) 29.6(7) 68.9(4) 95.9(6) 97.(6) 70.9(4) 30.0(7) 6.5(8) 93.8(5) 0.4(9) 90.7(7) 29.4(7) 00.6() 48.7() 90.9(4) 03.3(6) 02.8() 99.6(4) 2.7(6) Anales are in degrees. Estimated standard deviations in the least significant figure are given in parentheses. 3c 3,)'0
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 30 angle 36.5(4) C(0) 32.6(6) C() 29.0(7) Bi (2) S(6 Bi() Bi () 9.7() Bi (2) C() Bi () 48.0(2) a3ng3- le angle 29.3 (8) 3.6 8) 49.6() 86.8(4) 08.8(8) Bi() 04.8(6) C() 33.8(5) Bi() C(0) 36.7(4) 58.3 (8) Bi() 72.7() C() 29.0(6) Bi () 05.6(6) Bi () C() S() 46.0(5) Bi() C(0) 02.0(4) Bi () C() 56.9 (3 S{7) 55.7(6) Bi () C() 89() C(0) 3.9(4) Bi() C() 64.7(5) C(0) 32.0(7) S() C() 95.7(7) Bi (2) 54.5(2) S() C() 5() Bi (2) 43.7(4) S() C() 0.6(9) C(0) 4.(6) C() 34.8(9) Bi (2) C() 9.4(7) C() 32.0(4) Bi (2) 73.8(5) C() 55() 32.5(3) S() 96.4(7) C(0) 53.9(6) S() C() 35.9(7) C().8(7) S() 02.8(8) 3.7(5) C() 6() C(0) 30.2(7) 38.5(6) C() 90.4(8) C() 00() 20.(6) 97.3(8) C(0) C() 98.3(9) C() 7.0(6) Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 3 angle angle C (3) 94.4(7) 56.4(6) 36() 29() C (3) C() 54.8(7) 08() 37.8(6) 6.5 (5, 5() 97.3(7) C() 25.7(6) C( 7 ) 39.5(6) C() C (3) 07().5() 28() 03.8(7) Bi () 50.(5) C (7) 35.5(8) Bi() 59.8(4) 98() Bi() 94() Bi (2) 59.9(3) 97.5(8) 46.4(4) 6(2) 68.2(4) 36.3(9) 92() Bi (2) 47.9(5) 97.7(7) 6.(4) 32.9(4) 94() 35.8(8) 97.5(8) 4.4(8) 4() 6() 36.7(9) 56() 97.(8) 9.8(7) 36.6(9) C(0) 09() 95.4(7) C() 3.4(9) 7.6(5) C(0) 35.9(8) 3() C() 33.2(4) 39.0(6) C(0) C() 54() Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 32 angle angle C(0) 94.2(7) C(0) C (0) C() 38.8(7) 06.8(8) j,32 C (0) 4() C(0) C() 4.4(6) C (0) C() 99() C () 97.8(8) C() 56.4(7) C() C(0) 40.3 (6) C () C (2) 0() C() 50.7(8) C() C(0).(8) C() 35.(9) C() C (0) 26.9(5) C() C (2) 58(2) C(0) C() 49() 0.2(9) C() 39() C() 6() Angles are in degrees. Estimated standard deviations in the least significant figure are given in parentheses.
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 33 'I bis (pyridyl) -2-chloro-, 3-dithia-2-bismolane C0 C4 C5 X C>9 C3C Ca C2 NI X C7X N2 N2~ C I x SIXx Cx C SIX SI B xx S2 CI N2X C7 C8 C2X C3 C4 C5 C6 CIOx Clix
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 34 Table :Fractional ic positional parameters and equivalent isotropic temperature factors (A2) for C 2 H 4 BiClN 2 S 2 with e.s.d.s in parentheses. x y z U(eq) Bi() cl() S() N() N(2) C() H(A) H(B) H(2A) H(2B) H(3A) C (4) H(4A) H(5A) H (6A) H (7A) H(8A) H(9A) C(0) H(0A) C() H(A) H(2A) 03() 788(6) 547(6) 345(3) 272(9) -535() 3542(4) 4337(4) 3836(4) 3738(6) 29(6) 4904(6) 4098(3) 4468(3) 5060(3) 685(3) 4574(9) 5284(9) 366(22) 2782(22) 26(6) 2(6) -230(3) 576(3) -94(6) -703(6) -20(9) -267(9) -2327(6) -337(6) -603(4) -853(4) 6563 9865(4) 3845(4) 679(8) 6566(2) 6288(3) 3857(5) 464(5) 2767(5) 4895(5) 466(5) 4775(5) 7235(4) 7936(4) 7054(8) 7589(8) 6200(6) 6080(6) 5473(23) 4750(23) 5677(8) 546(8) 744(4) 804(4) 6988(9) 765(9) 5858(20) 5653(20) 4957(8) 406(8) 599(6) 4539(6) 23() 569(6) 587(6) 380(3) -38(8) 2808() 34(4) 2686(4) 359(4) 4430(5) 4854(5) 5367(5) 409(3) 400(3) -309(6) 42(6) -583(9) -274(9) -29(20) -3096(20) -369(5) -793(5) 407(4) 4274(4) 495(4) 5946(4) 466(7) 5308(7) 3386(8) 306(8) 70(5) 469(5) 34() 52() 46() 49() 50(2) 52(4) 58(3) 70 70 66(4) 80 80 72(4) 86 85(6) 02 90(6) 09 22(7) 46 86(5) 03 7(4) 85 85(7) 02 0(8) 32 94(6) 3 73(4) 88
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 35 Table :Interic distances (A) for C 2 H 4 BiClN 2 S 2. j3d, D 3'S-- Bi() -N() Bi() - Bi() -S() Bi() -N(2) Bi()-C() S() -C() - N() - N() - N(2)- N(2)- C()- C() -H(IA) C() -H(B) -H(2A) -H(2B) - -H(3A) - -H(4A) - -H(5A) c(6)- -H(6A) -H(7A) - -H(8A) c(9) -C(0) -H(9A) C(0)-C() C(0)-H(0A) c()- C()-H(A) -H(2A) 2.534(8) 2.542(6) 2.545(4) 2.592(9) 3.(4).822(3).83(2).336(2).35(4).336(2).362(3).52(2).08.08.08.08.400(2).08.362(4).08.38(2).08.393(4).08.08.372(3).08.40(2).08.376(4).08.378(3).08.08
(0996 American Chemical Society J Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 36 Table :Intramolecular bond angles (degrees) involving non-hydrogen s for C 2 H 4 BCIN 2 S 2. N()-Bi()- N()-Bi(-S() -Bi()-S() N()-Bi()-N(2) -Bi()-N(2) S()-Bi()-N(2) N(2)-Bi()-C() s(2)-st()-cl() S()-Bi()-C() N(2)-Bi()-C() C()-S()-Bi() --Bi() -N()- -N()-Bi() c(7)-n()-bi() -N(2)-0(2) -N(2)-Bi() 0(2)-N(2)-Bi() -C()-S() c(2)-c()-h(a) S()-C()-H(A) c(2)-c()-h(b) S()-c()-H(B) H(A)-C()-H(B) C()-0(2)- C()--H(2A) --H(2A) C()--H(2B) --H(2B) H(2A)--H(2B) N()-- N()--H(3A) 0(4)--H(3A) c(5)-c(4)-c(3) --H(4A) 0(3)--H(4A) -0(5)-0(6) --H(5A) 0(6)--H(5A) c(5)-c(6)-0(7) --H(6A) --H(6A) N()--0(6) N()--H(7A) c(6)-0(7)-h(7a) N(2)-- N(2)--H(8A) c(9)-c(8)-h(8a) --C(0) c(8)-c(9)-h(9a) c(0)-c(9)-h(9a) 89.8(2) 86.3(4) 84.8(2) 73.(4) 86.6(2) 87.5(3) 82.8(4) 75.3(2) 57.26(9) 0.9(3) 00.2(5) 00.5(5) 20.0(9) 23.5(8) 5.9(8) 9.(9) 20.9(8) 9.9(8) 2.3(9) 09.3(8) 09.2(5) 09.6(7) 08.3(5) 08.0 2.3(9) 09.4(8) 09.3(5) 09.(7) 08.7(4) 08.0 20.5(0) 9.6(7) 9.8(7) 9.8() 9.9(7) 20.3(7) 9.7() 20.7(7) 9.6(7) 8.7() 2.0(7) 20.3(8) 2.2() 8.9(6) 9.9(8) 23.4() 20.(6) 6.5(8) 7.6() 25.0(8) 7.4(8)
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 37 _a) 3, -/3 ) C()-C(0)- C()-C(0)-H(0A) -C(0)-H(0A) C(0)-C()- C(0)-C()-H(A) -C()-H(A) N(2)--C() N(2)--H(2A) C()--H(2A) 9.4() 8.6(8) 22.0(8) 20.0() 2.5(8) 8.5(8) 20.5(0) 7.8(6) 2.7(8)
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 38 Table :Special contacts (A) involving non-hydrogen s for C 2 H 4 BiCIN 2 S 2 * Bi() *Bi() * Bi() *Bi() Bi() Bi(i) Bi() Bi() Bi() Bi() Bi() B() Bi() Bi() Bi() 0() 0() Cl() S() S() s() N() N() N(2) N(2) C() c(9) C(0) C() -Bi() -Bi() -cl() -C() -s() -S() - -N() -N(2) -c() - - - - - -S() -S() - - -c() - -c() - - - - - - - - - - - -c(0) -C() - 5.46( 0) 5.46( 0) 3.( 5) 3.23( 5) 2.545( 5) 3.443( 5) 2.542( 4) 2.53 ( ) 2.59 ( ) 3.38 ( ) 3.39 ( ) 3.46 ( ) 3.35 ( 2) 3.47 ( ) 3.48 ( ) 3.672( 7) 3.409( 7) 3.483( 7) 3.429( 7).82 ( ) 2.78 ( 2) 2.79 ( ).83 C 2).34 ( 2).35 ( 2).34 ( 2).36 ( 2).52 ( 2).40 C 2).36 ( 2).38 ( 3).39 ( 3).37 ( 2).40 ( 2).38 ( 2).38 ( 2) IDENTITY IDENTITY IDENTITY IDENTITY IDENTITY IDENTITY -x -x Y +-0.500 Y + 0.500 -x Y +-0.500 -x Y + 0.500 x -x Y +.000 Y + 0.500 -Z -Z -Z -Z z -Z +,Cxuf-- < *ik:a~ f~y- 4h.ra c.ordosz9 d~*ci xcz~z~
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 39 < 0. Table Anisotropic displacement parameters (A 2 x 03) for C 2 Hj 4 BiCN 2 S 2 The anisotropic displacement factor exponent takes the form: -2 w ( h 2 a*2 U +... + 2 hk a* b* Ul2 ] Ull U22 U33 U23 U3 U2 Bi() 35() 30() 33() 2() 2() 3() CL() 54(2) 33(2) 57(3) -2(2) 6(2) -(2) S() 50(2) 28(2) 45(2) -(2) 8(2) 3(2) 44() 49(3) 40() -6(2) 7() -6(2) N(l) 5(5) 55(5) 4(4) 8() 8(4) 0() N(2) 46(5) 57(2) 56(6) -3(6) 26(5) -2(5) C() 58(7) 46(7) 55(7) -4(7) 3(6) 3(7) 68(8) 63(9) 47(7) 0(7) 8(6) 20(8) 73(8) 89() 67(8) 5(8) 44(7) -4(8) 58(7) 3(9) 97(0) 33(2) 46(8) 3(9) 3(5) 66(6) 23(4) 7(0) 00(4) 2(9) 98(22) 06(6) 9(5) -37(4) 23(7) -25(7) 07(2) 08(3) 67(0) -7(0) 6(0) -2() 57(7) 88(3) 7(8) -2(8) 32(7) -2(7) 72(9) 6(22) 72(8) -7(0) 36(8) 9() C(0) 08(4) 7(23) 78(2) 39(3) 65(2) 72(5) C() 62(9) 26(6) 09(3) 30(3) 52(0) -(0) 57(8) 93(2) 79(0) -6(9) 39(8) -7(9)
(0996 American Chemical Society J. Am. Chem. Soc. V8 Page3225 Agocs Supplemental Page 40,J,) 3,; -L/D OBSERVED AND CALCULATED STRUCTURE FACTORS FOR C4HgBiCIS 3. An * indicates weak relfections not used in the final refinements. k Fo Fc sigf k Fo Fc sigf k Fo Fc sigf AAAAAA^ h - 0 AAAAAAA -0-8 -6-4 -2-9 -7-5 -3 - -0-8 -6-4 -2 0-9 -7-5 -3 - -8-6 -4-2 0-9 -7-5 -3 - -8-6 -4-2 0-7 -5-3 - -8-6 -4-2 0-7 -5-3 467 64 54 9 552 00 803 56 997 27 7 323 06 73 527 3250 76 759 379 045 708 55 677 384 052 806 682 77 384 575 847 574 750 404 843 2308 636 433 287 68 404 350 25 476 920 278 334 453 7 537 94 69 25 02 826 5 965 26 27 750 358 000 92 * 59 25 3323 26 204 747 383 035 693 25 35 668 375 036 76 25 664 58 408 542 803 545 742 39 786 2263 25 655 409 279 53 43 355 67 * 476 97 372 94 330 9 0 0 0 0 2 2 2 3 - -6-4 -2 0-5 -3 - -4-2 0 - AAAAAAA h - -0-9 -8-7 -6-5 -4-3 -2 - -0-9 -8-7 -6-5 -4-3 -2 - -9-8 -7-6 -5-4 -3-2 - -9-8 -7-6 -5-4 50 65 54 0 95 0 74 39 92 0 47 34 86 206 7 387 445 660 02 356 375 370 822 33 46 232 49 45 96 95 237 562 82 99 520 264 543 455 2544 325 03 48 22 353 294 34 8 90 29 53 2 232 42 94 203 78 7 279 25 ^^^^^ 63 77 2 403 444 690 069 343 363 380 823 36 238 434 44 7 78 253 54 48 98 55 250 548 447 98 299 039 45 7 359 276 328 5 * * * * * * * * * * * * * 26 25 * * 25 25 25 * 25 92 038 078 0 95 496 298 96 340 786 2 77 76 49 0 867 79 572 327 937 88 37 67 262 274 85 50 309 550 583 03 60 544 0 905 470 587 295 6 57 23 466 0 645 04 274 4 295 38 320 56 * 032 050 4 * 64 * 47 29 22 34 74 25 99 78 55 * 26 * 36 * 85 37 * 563 345 927 8 * 00 * 92 * 0 260 87 52 280 523 563 22 * 72 * 532 22 * 92 49 584 285 57 * 57 * 75 * 496 05 * 706 7 * 293 29 * 33 2 * 429