3F-nondecomposition

Table 1 Crystal data and structure refinement for 3F-nondecomposition.
Identification code 3F-nondecomposition
Empirical formula C42H42F3.27N2O6
Formula weight 732.90
Temperature/K 293(2)
Crystal system triclinic
Space group P-1
a/Å 7.453
b/Å 14.683
c/Å 20.135
α/° 66.42
β/° 79.76
γ/° 93.67
Volume/Å3 1964.9
Z 2
ρcalcg/cm3 1.239
μ/mm‑1 0.090
F(000) 771.0
Crystal size/mm3 0.05 × 0.01 × 0.01
Radiation Synchrotron (λ = 0.68882)
2Θ range for data collection/° 2.856 to 46.636
Index ranges -8 ≤ h ≤ 8, -16 ≤ k ≤ 16, -22 ≤ l ≤ 22
Reflections collected 16866
Independent reflections 5707 [Rint = 0.0826, Rsigma = 0.0628]
Data/restraints/parameters 5707/105/523
Goodness-of-fit on F2 1.618
Final R indexes [I>=2σ (I)] R1 = 0.1392, wR2 = 0.4116
Final R indexes [all data] R1 = 0.1852, wR2 = 0.4455
Largest diff. peak/hole / e Å-3 0.36/-0.38

 

Table 2 Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 3F-nondecomposition. Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.
AtomxyzU(eq)
O115560(5)-1359(3)6361(2)103.1(12)
O29839(6)1921(3)4950(2)118.4(14)
O311258(6)-1291(4)7115(2)117.7(14)
O414557(8)2475(3)5545(2)135.3(17)
O515977(7)-1221(3)7409(2)127.5(15)
C615083(7)295(4)5605(3)95.0(16)
O79849(9)2562(4)5796(3)145.8(19)
C89942(8)947(5)4920(4)107.3(18)
C915270(7)-686(4)5649(3)97.4(16)
C1014736(7)865(5)7452(3)102.2(17)
N1114203(7)2497(4)6711(3)108.5(15)
C1210082(8)732(5)6144(3)102.8(17)
C1315162(8)260(5)6357(3)101.8(17)
C1414282(8)1826(5)7436(3)106.0(18)
N1510329(7)-837(4)8098(3)113.3(16)
C1614884(8)85(5)8148(3)112.1(19)
C1710121(7)204(5)5629(3)102.5(17)
C1815209(7)-1042(4)5089(3)95.1(16)
C1914892(8)966(5)6665(3)103.8(17)
C2010126(7)364(4)6910(3)103.0(17)
C219818(8)796(5)4300(3)105.9(18)
C2213963(10)1976(7)8102(4)115(2)
C239309(9)1778(6)7416(4)118(2)
C2414092(11)1176(7)8775(4)127(2)
C259883(9)60(5)8175(4)114.2(19)
C269543(10)225(7)8818(5)126(2)
F2714687(11)-583(6)9445(3)167(5)
C2810606(8)-682(5)7354(3)104.2(18)
C299749(8)838(5)7464(3)102.8(17)
F3013469(11)2772(7)8112(4)143(4)
C3114571(9)2044(5)6228(3)106.9(18)
C329088(11)1155(7)8777(6)138(3)
F339708(13)-445(7)9444(4)150(5)
C349899(9)1811(5)5673(4)113.8(19)
C3513740(9)3551(5)6475(4)116.2(19)
C3610763(10)-1756(6)8692(4)130(2)
C3714531(10)282(7)8807(4)127(2)
C3815569(8)-793(4)6778(4)105.4(18)
F398598(13)2902(7)7967(5)151(5)
C4017038(15)4469(8)5877(5)181(4)
F4113737(12)1230(6)9413(4)153(5)
C428969(10)1919(7)8089(6)136(2)
C4315315(13)4373(6)6403(5)151(3)
F448939(17)1451(8)9322(5)159(6)
C458954(17)-2542(7)9194(6)206(5)
C4618839(13)5022(8)5997(7)193(4)
C4714560(15)5378(6)6251(5)169(3)
C489680(20)-3432(8)9812(7)251(7)
C497790(19)-2931(13)8817(9)281(8)
C5010640(50)6275(19)7341(17)299(11)
C5112320(30)6379(10)6756(11)237(7)
C5210720(30)-3302(12)10322(10)335(9)
C535850(20)-3380(13)9265(11)331(9)
C5713220(20)5407(8)6944(7)221(5)
C111330(40)-4321(15)10781(15)429(14)
C213030(40)-4150(20)11078(19)479(18)
C49A6880(30)-2490(50)9350(60)281(8)
C51A13780(100)5960(30)7370(30)237(7)
C50A13270(70)6160(20)7930(20)299(11)
C22A13963(10)1976(7)8102(4)115(2)
C24A14092(11)1176(7)8775(4)127(2)
C37A14531(10)282(7)8807(4)127(2)
C42A8969(10)1919(7)8089(6)136(2)
C32A9088(11)1155(7)8777(6)138(3)
C26A9543(10)225(7)8818(5)126(2)

 

Table 3 Anisotropic Displacement Parameters (Å2×103) for 3F-nondecomposition. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
AtomU11U22U33U23U13U12
O1102(3)106(3)80(2)-19(2)-21.7(18)6(2)
O2132(3)101(3)106(3)-25(2)-33(2)13(2)
O3118(3)124(3)90(3)-26(2)-17(2)25(3)
O4195(5)111(3)92(3)-33(2)-43(3)8(3)
O5151(4)133(3)94(3)-34(2)-51(3)23(3)
C681(3)103(4)82(3)-24(3)-16(2)-6(3)
O7208(6)115(4)105(3)-33(3)-40(3)27(3)
C888(4)108(5)100(4)-21(3)-17(3)2(3)
C987(4)106(4)78(3)-20(3)-17(2)-2(3)
C1083(3)119(5)84(4)-26(3)-20(3)-9(3)
N11110(3)111(4)89(3)-27(3)-25(2)-1(3)
C1288(4)105(4)94(4)-26(3)-11(3)3(3)
C1389(4)117(4)76(3)-20(3)-19(2)-10(3)
C1490(4)121(5)88(4)-37(3)-2(3)-12(3)
N15102(3)128(4)89(3)-23(3)-28(2)1(3)
C16100(4)136(5)79(4)-32(3)-12(3)-15(3)
C1785(4)94(4)100(4)-16(3)-15(3)0(3)
C1877(3)111(4)80(3)-28(3)-9(2)0(3)
C1996(4)111(4)90(4)-29(3)-25(3)-5(3)
C2082(3)97(4)105(4)-23(3)-11(3)3(3)
C21101(4)106(5)86(4)-17(3)-21(3)4(3)
C22107(5)132(6)89(4)-37(4)-10(3)-5(4)
C2396(4)120(5)132(6)-45(4)-30(4)1(3)
C24131(5)148(7)81(4)-35(4)-11(3)-14(5)
C2593(4)118(5)124(6)-46(4)-23(3)-4(3)
C26115(5)128(6)135(7)-53(6)-31(4)3(4)
F27188(8)187(8)93(5)-33(4)-20(4)-3(5)
C2893(4)119(5)85(4)-28(3)-21(3)2(3)
C2988(4)106(4)100(4)-38(3)-9(3)-6(3)
F30152(6)159(8)110(5)-62(4)-6(4)-2(5)
C31122(5)104(4)84(4)-32(3)-24(3)-10(3)
C32116(5)136(7)145(7)-46(6)-27(5)-8(4)
F33192(9)140(7)87(6)-23(5)-23(5)-4(5)
C34125(5)99(5)104(5)-30(4)-26(3)12(4)
C35109(4)123(5)110(4)-43(4)-29(3)1(4)
C36120(5)146(6)96(4)-20(4)-29(3)13(4)
C37117(5)135(6)89(5)-15(4)-17(3)-13(4)
C3896(4)104(4)100(4)-25(4)-32(3)-1(3)
F39150(8)140(9)166(9)-78(6)-18(5)-3(5)
C40199(10)167(8)139(7)-42(6)-16(7)-26(7)
F41176(8)170(7)90(6)-52(4)0(4)-20(5)
C42112(5)135(7)168(8)-75(6)-26(5)2(4)
C43153(7)122(6)134(6)-29(4)-4(5)-22(5)
F44210(11)155(9)95(7)-59(6)9(6)-5(7)
C45219(9)122(6)180(8)38(6)-72(7)-17(6)
C46130(7)185(9)246(11)-78(8)-46(7)-29(6)
C47224(10)107(5)155(6)-35(5)-51(6)5(5)
C48336(16)175(9)165(9)13(7)-103(9)-56(10)
C49171(8)262(11)224(12)91(8)-99(7)-88(8)
C50450(20)189(13)273(19)-153(15)21(16)38(16)
C51371(18)114(8)204(12)-77(8)0(10)-1(8)
C52490(20)253(14)212(13)-11(11)-188(13)-23(14)
C53178(10)250(13)400(20)16(12)-46(10)-53(10)
C57313(13)147(7)197(9)-83(7)-22(8)2(7)
C1550(30)350(20)330(20)-17(19)-268(19)60(20)
C2580(40)510(40)540(40)-290(30)-360(30)220(30)
C49A171(8)262(11)224(12)91(8)-99(7)-88(8)
C51A371(18)114(8)204(12)-77(8)0(10)-1(8)
C50A450(20)189(13)273(19)-153(15)21(16)38(16)
C22A107(5)132(6)89(4)-37(4)-10(3)-5(4)
C24A131(5)148(7)81(4)-35(4)-11(3)-14(5)
C37A117(5)135(6)89(5)-15(4)-17(3)-13(4)
C42A112(5)135(7)168(8)-75(6)-26(5)2(4)
C32A116(5)136(7)145(7)-46(6)-27(5)-8(4)
C26A115(5)128(6)135(7)-53(6)-31(4)3(4)

 

Table 4 Bond Lengths for 3F-nondecomposition.
AtomAtomLength/Å AtomAtomLength/Å
O1C91.444(6) C20C281.541(9)
O1C381.399(8) C20C291.530(9)
O2C81.460(8) C21C1721.421(9)
O2C341.409(8) C22C241.418(11)
O3C281.259(7) C22F301.254(10)
O4C311.265(7) C23C291.408(9)
O5C381.274(7) C23C421.434(11)
C6C91.425(9) C24F411.301(9)
C6C131.506(8) C25C261.394(10)
C6C1811.454(8) C25C291.457(9)
O7C341.224(8) C26C321.401(12)
C8C171.443(8) C26F331.284(11)
C8C211.370(9) C32C421.414(12)
C9C181.425(8) C32F441.324(12)
C10C141.461(9) C35C431.573(10)
C10C161.440(8) C36C451.598(12)
C10C191.513(9) F39C421.418(12)
N11C141.413(8) C40C431.472(12)
N11C311.381(8) C40C461.630(13)
N11C351.509(8) C43C471.548(12)
C12C171.522(9) C45C481.605(12)
C12C201.422(9) C45C491.473(19)
C12C341.517(10) C45C49A1.54(2)
C13C191.414(9) C47C571.582(15)
C13C381.518(8) C48C521.457(17)
C14C221.426(10) C49C531.51(2)
N15C251.439(9) C50C511.51(3)
N15C281.396(8) C51C571.55(2)
N15C361.502(9) C52C11.558(16)
C16C371.451(10) C53C49A1.56(2)
C17C2121.421(9) C57C51A1.49(5)
C18C611.454(8) C1C21.540(17)
C19C311.532(9) C51AC50A1.28(5)

13-X,-Y,1-Z; 22-X,-Y,1-Z

 

Table 5 Bond Angles for 3F-nondecomposition.
AtomAtomAtomAngle/˚ AtomAtomAtomAngle/˚
C38O1C9105.8(4) C26C25N15128.4(7)
C34O2C8108.6(5) C26C25C29120.8(7)
C9C6C13106.6(5) C25C26C32119.5(9)
C9C6C181117.5(5) F33C26C25121.2(8)
C181C6C13135.8(6) F33C26C32119.2(9)
C17C8O2110.3(6) O3C28N15123.5(6)
C21C8O2122.7(6) O3C28C20128.4(6)
C21C8C17126.9(6) N15C28C20107.9(6)
C6C9O1112.5(5) C23C29C20134.6(6)
C6C9C18128.0(5) C23C29C25120.1(6)
C18C9O1119.5(5) C25C29C20105.3(6)
C14C10C19105.5(5) O4C31N11123.2(6)
C16C10C14118.7(6) O4C31C19127.9(6)
C16C10C19135.8(7) N11C31C19108.8(5)
C14N11C35126.5(5) C26C32C42120.3(9)
C31N11C14110.2(5) F44C32C26125.6(10)
C31N11C35123.2(5) F44C32C42113.7(9)
C20C12C17131.4(6) O2C34C12109.4(6)
C20C12C34123.5(6) O7C34O2117.5(6)
C34C12C17105.1(5) O7C34C12133.1(7)
C6C13C38103.3(6) N11C35C43115.8(6)
C19C13C6132.5(6) N15C36C45112.3(6)
C19C13C38124.2(6) O1C38C13111.4(5)
N11C14C10110.8(5) O5C38O1116.3(5)
N11C14C22128.9(7) O5C38C13132.2(6)
C22C14C10120.3(6) C43C40C46114.0(8)
C25N15C36126.0(6) C32C42C23121.8(8)
C28N15C25110.2(6) C32C42F39125.8(9)
C28N15C36123.0(7) F39C42C23112.3(9)
C10C16C37118.4(7) C40C43C35114.1(7)
C8C17C12106.6(6) C40C43C47113.6(7)
C212C17C8117.4(6) C47C43C35109.6(7)
C212C17C12135.9(5) C36C45C48104.9(9)
C9C18C61114.5(5) C49C45C36117.7(10)
C10C19C31104.6(6) C49C45C48111.7(10)
C13C19C10131.2(6) C49AC45C36135(3)
C13C19C31124.0(6) C49AC45C48117(4)
C12C20C28123.2(6) C43C47C57114.8(8)
C12C20C29131.5(6) C52C48C45124.9(12)
C29C20C28105.4(5) C45C49C53114.1(18)
C8C21C172115.7(6) C50C51C57113.1(16)
C24C22C14118.6(9) C48C52C1109.3(16)
F30C22C14121.6(7) C51C57C47113.7(11)
F30C22C24119.7(8) C51AC57C47123(3)
C29C23C42117.5(7) C2C1C52110.9(16)
F41C24C22122.8(10) C45C49AC53107.8(19)
N15C25C29110.8(6) C50AC51AC57145(5)

13-X,-Y,1-Z; 22-X,-Y,1-Z

 

Table 6 Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 3F-nondecomposition.
AtomxyzU(eq)
H16A15198-5298174135
H1615198-5298174135
H18A14225-16075281114
H18B16360-12854987114
H21970213143861127
H23A924122876964142
H23924122876964142
H35A1266735406831139
H35B1340137515998139
H36A11385-15559007157
H36B11597-20808461157
H3714608-2179261152
H40A1688748465375217
H40B1725838035925217
H431561541536893181
H458183-22139450247
H45A8910-28788862247
H46A1991350455645289
H46B1900346546492289
H46C1866256945926289
H47A1390855165853202
H47B1559559136079202
H48A8599-392110119301
H48B10426-37519548301
H49A8369-34408702337
H49B7734-23878350337
H50A1023269177226449
H50B1095460417819449
H50C967558037351449
H51A1322569246701285
H51B1196765566284285
H52A9967-307610655403
H52B11802-279610045403
H53A5889-39239727496
H53B5183-36288991496
H53C5245-28749362496
H53D6102-32618750496
H53E4547-34359443496
H53F6270-39939548496
H57A1225048327150266
H57B1390453457323266
H57C1214256686774266
H57D1280647137299266
H1A10323-473411195514
H1B11621-467710470514
H2A14015-372510670718
H2B13414-478511339718
H2C12719-383511410718
H49C6623-18549005337
H49D6463-25409852337
H51C1492357117463285
H51D1416166326976285
H50D1260167247793449
H50E1433163268091449
H50F1248355898328449
H22A1367525878096138
H24A1386712709210153
H42A866125308073164
H32A886312709204165
H26A9618-2789272152

 

Table 7 Atomic Occupancy for 3F-nondecomposition.
AtomOccupancy AtomOccupancy AtomOccupancy
H16A0.10(2) H160.90(2) C220.90(2)
H23A0.10(2) H230.90(2) C240.90(2)
C260.10(2) F270.649(18) F300.604(18)
C320.10(2) F330.525(17) C370.10(2)
H370.10(2) F390.491(17) F410.555(17)
C420.10(2) F440.447(18) H450.90(2)
H45A0.10(2) C490.90(2) H49A0.90(2)
H49B0.90(2) C500.570(16) H50A0.570(16)
H50B0.570(16) H50C0.570(16) C510.742(16)
H51A0.742(16) H51B0.742(16) H53A0.90(2)
H53B0.90(2) H53C0.90(2) H53D0.10(2)
H53E0.10(2) H53F0.10(2) H57A0.742(16)
H57B0.742(16) H57C0.258(16) H57D0.258(16)
C49A0.10(2) H49C0.10(2) H49D0.10(2)
C51A0.258(16) H51C0.258(16) H51D0.258(16)
C50A0.430(16) H50D0.430(16) H50E0.430(16)
H50F0.430(16) C22A0.10(2) H22A0.10(2)
C24A0.10(2) H24A0.10(2) C37A0.90(2)
C42A0.90(2) H42A0.90(2) C32A0.90(2)
H32A0.90(2) C26A0.90(2) H26A0.90(2)

Experimental

Single crystals of C42H42F3.27N2O6 [3F-nondecomposition] were []. A suitable crystal was selected and [] on a diffractometer. The crystal was kept at 293(2) K during data collection. Using Olex2 [1], the structure was solved with the XS [2] structure solution program using Direct Methods and refined with the ShelXL [3] refinement package using CGLS minimisation.

  1. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.

Crystal structure determination of [3F-nondecomposition]

Crystal Data for C42H42F3.27N2O6 (=732.90 g/mol): triclinic, space group P-1 (no. 2), a = 7.453 Å, b = 14.683 Å, c = 20.135 Å, α = 66.42°, β = 79.76°, γ = 93.67°, = 1964.9 Å3, Z = 2, T = 293(2) K, μ(Synchrotron) = 0.090 mm-1, Dcalc = 1.239 g/cm3, 16866 reflections measured (2.856° ≤ 2Θ ≤ 46.636°), 5707 unique (Rint = 0.0826, Rsigma = 0.0628) which were used in all calculations. The final R1 was 0.1392 (I > 2σ(I)) and wR2 was 0.4455 (all data).

Refinement model description

Number of restraints - 105, number of constraints - unknown.

Details:

1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Shared sites
{C22, C22A}
{C24, C24A}
{C37A, C37}
{C42A, C42}
{C32A, C32}
{C26A, C26}
3. Restrained distances
C52-C1 = C2-C1 = C48-C45 = C49A-C45
1.55 with sigma of 0.02
C2-C52
2.5 with sigma of 0.02
C28-C20
1.4 with sigma of 0.02
C13-C38
1.4 with sigma of 0.02
C53-C49A
1.55 with sigma of 0.02
4. Rigid bond restraints
C2, C1, C52, C48
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
C47, C57, C51, C51A, C50A, C50
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
C45, C49A, C49, C53
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C48 ≈ C52 ≈ C1 ≈ C2: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C47 ≈ C57 ≈ C51 ≈ C51A ≈ C50A ≈ C50: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C53 ≈ C49 ≈ C49A ≈ C45: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C49) = Uanis(C49A)
Uanis(C50) = Uanis(C50A)
Uanis(C51) = Uanis(C51A)
Uanis(C37) = Uanis(C37A)
Uanis(C22) = Uanis(C22A)
Uanis(C24) = Uanis(C24A)
Uanis(C37A) = Uanis(C37)
Uanis(C42) = Uanis(C42A)
Uanis(C32) = Uanis(C32A)
Uanis(C26) = Uanis(C26A)
Uanis(C42A) = Uanis(C42)
Uanis(C32A) = Uanis(C32)
Uanis(C26A) = Uanis(C26)
6. Others
Sof(H16A)=Sof(H23A)=Sof(C26)=Sof(C32)=Sof(C37)=Sof(H37)=Sof(C42)=Sof(H45A)=
Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(C49A)=Sof(H49C)=Sof(H49D)=Sof(C22A)=
Sof(H22A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
Sof(H16)=Sof(C22)=Sof(H23)=Sof(C24)=Sof(H45)=Sof(C49)=Sof(H49A)=Sof(H49B)=
Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(C37A)=Sof(C42A)=Sof(H42A)=Sof(C32A)=
Sof(H32A)=Sof(C26A)=Sof(H26A)=FVAR(1)
Sof(H57C)=Sof(H57D)=Sof(C51A)=Sof(H51C)=Sof(H51D)=1-FVAR(2)
Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H57A)=Sof(H57B)=FVAR(2)
Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(3)
Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
C43(H43), C45(H45), C45(H45A)
7.b Secondary CH2 refined with riding coordinates:
C18(H18A,H18B), C35(H35A,H35B), C36(H36A,H36B), C40(H40A,H40B), C47(H47A,
H47B), C48(H48A,H48B), C49(H49A,H49B), C51(H51A,H51B), C52(H52A,H52B),
C57(H57A,H57B), C57(H57C,H57D), C1(H1A,H1B), C49A(H49C,H49D), C51A(H51C,H51D)
7.c Me refined with riding coordinates:
C46(H46A,H46B,H46C), C50(H50A,H50B,H50C), C53(H53A,H53B,H53C), C53(H53D,H53E,
H53F), C2(H2A,H2B,H2C), C50A(H50D,H50E,H50F)
7.d Aromatic/amide H refined with riding coordinates:
C16(H16A), C16(H16), C21(H21), C23(H23A), C23(H23), C37(H37), C22A(H22A),
C24A(H24A), C42A(H42A), C32A(H32A), C26A(H26A)

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