06F

Table 1 Crystal data and structure refinement for 06F.
Identification code 06F
Empirical formula C42H41F3.37N2O6
Formula weight 733.70
Temperature/K 293(2)
Crystal system triclinic
Space group P-1
a/Å 7.442
b/Å 14.635
c/Å 19.312
α/° 108.27
β/° 98.49
γ/° 93.69
Volume/Å3 1961.7
Z 2
ρcalcg/cm3 1.242
μ/mm‑1 0.088
F(000) 771.0
Crystal size/mm3 0.5 × 0.06 × 0.02
Radiation Synchrotron Monochromator X-ray (λ = 0.68882)
2Θ range for data collection/° 2.86 to 46.64
Index ranges -7 ≤ h ≤ 7, -16 ≤ k ≤ 16, -22 ≤ l ≤ 22
Reflections collected 20424
Independent reflections 5738 [Rint = 0.0902, Rsigma = 0.0574]
Data/restraints/parameters 5738/49/509
Goodness-of-fit on F2 1.367
Final R indexes [I>=2σ (I)] R1 = 0.1133, wR2 = 0.3283
Final R indexes [all data] R1 = 0.1449, wR2 = 0.3671
Largest diff. peak/hole / e Å-3 0.40/-0.26

 

Table 2 Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 06F. Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.
AtomxyzU(eq)
O0AA3097(4)5017(2)3650.8(14)106.6(9)
O26631(4)4188(3)2897.8(16)115.7(10)
O310204(4)3131(2)5061.6(16)118.2(10)
O8AA4871(5)1971(2)4455.6(18)136.1(12)
O51631(4)3821(2)2606.7(17)128.0(11)
N16552(5)2745(3)1909.5(18)109.2(11)
C1AA4737(5)5938(3)4908(2)99.8(12)
C2AA1989(6)1784(4)1868(2)112.1(14)
C3AA4316(5)4110(3)4399(2)97.2(11)
O4AA9309(5)1617(3)4201.3(19)141.5(13)
C5AA4105(5)5059(3)4355(2)96.3(11)
C6AA2809(5)1677(3)2553(2)103.2(12)
C9AA10130(5)4109(3)5065(2)102.9(12)
C0BA8756(5)3122(3)3854(2)100.8(12)
N64108(5)783(3)3294.1(19)108.0(11)
C77032(6)3333(4)2648(2)104.1(13)
C7AA6986(4)1771(2)1846.7(16)105.1(13)
C207769(4)1698(2)2524.0(12)103.0(12)
C148260(4)815(3)2567.1(15)115.9(14)
C287969(5)4(2)1933(2)125.8(15)
C187186(5)77(2)1255.6(15)127.6(16)
C176695(4)961(3)1212.5(12)125.6(16)
C89251(5)4150(3)4363(2)99.8(12)
C43465(5)3390(3)3648(2)97.4(12)
C93275(6)738(3)2565(2)107.3(13)
C1BA3441(5)2372(3)3338(2)101.7(12)
C107955(5)2717(3)3096(2)98.8(12)
C119139(5)5113(3)4308(2)102.4(12)
C122169(7)50(4)1227(3)124.5(16)
C135575(6)3094(4)1318(3)124.7(15)
F153520(7)-961(4)1883(2)132(2)
F16910(8)1067(4)558(2)148(2)
C192964(7)-63(4)1905(2)118.2(15)
C211680(7)966(4)1219(2)125.3(16)
F221878(8)-720(4)590(2)153(2)
C234810(6)-34(3)3528(3)120.1(14)
F245823(10)993(4)513(3)149(3)
F258387(9)-901(4)1969(3)159(3)
C262628(5)4034(3)3219(2)103.3(12)
C279393(6)2507(4)4341(2)112.3(13)
C294231(6)1738(3)3789(2)105.0(12)
C303277(8)-774(4)3604(3)144.1(19)
C312030(10)-353(5)4137(4)135(2)
C326849(11)3391(7)815(4)198(3)
F336729(11)-749(5)617(3)174(4)
C344235(10)-1662(5)3749(4)172(3)
C35155(10)-1010(6)4008(5)191(3)
C365500(14)3705(8)212(5)238(4)
C374851(16)-2340(6)3073(5)219(4)
C388410(10)4187(9)1224(5)267(5)
C396040(20)-3151(8)3220(8)253(7)
C409880(17)4137(14)732(10)400(10)
C413920(20)2979(10)-320(7)325(7)
C432720(20)3476(11)-775(9)403(10)
C477210(40)-3628(11)2625(10)320(11)
C39A3340(40)-3205(16)2719(17)253(7)
C47A4040(60)-4022(16)2148(18)320(11)
C31A1340(30)-750(15)3371(11)135(2)
C6920(20)2937(15)-1216(14)500(16)
C28A7969(5)4(2)1933(2)125.8(15)
C18A7186(5)77(2)1255.6(15)127.6(16)
C17A6695(4)961(3)1212.5(12)125.6(16)
C19A2964(7)-63(4)1905(2)118.2(15)
C12A2169(7)50(4)1227(3)124.5(16)
C21A1680(7)966(4)1219(2)125.3(16)

 

Table 3 Anisotropic Displacement Parameters (Å2×103) for 06F. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
AtomU11U22U33U23U13U12
O0AA109.2(19)127(2)83.7(17)44.4(15)2.0(13)1.5(15)
O2113(2)144(3)96.5(19)52.9(18)8.7(14)16.1(18)
O3131(2)126(2)105(2)56.5(17)4.1(16)8.5(16)
O8AA174(3)126(2)98(2)44.0(17)-14.3(19)-6(2)
O5125(2)147(3)103(2)49.3(18)-18.5(17)-2.6(18)
N1102(2)142(3)85(2)47(2)6.5(16)-7.3(19)
C1AA91(2)128(3)86(2)50(2)9.6(18)-4(2)
C2AA106(3)139(4)88(3)43(2)5(2)-19(2)
C3AA88(2)123(3)81(2)40(2)11.8(17)-5.6(19)
O4AA175(3)127(3)118(2)55(2)-11(2)-1(2)
C5AA88(2)124(3)79(2)44(2)6.7(17)-5(2)
C6AA89(2)129(3)88(3)38(2)10.4(18)-15(2)
C9AA96(3)128(3)94(3)52(2)14(2)7(2)
C0BA90(2)124(3)95(3)48(2)15.1(19)3(2)
N6112(2)120(3)93(2)45(2)8.2(17)-8.9(18)
C792(3)134(4)91(3)50(3)8.3(19)-4(2)
C7AA106(3)121(3)87(3)37(2)14(2)-6(2)
C2095(3)117(3)102(3)46(2)18(2)-4(2)
C14106(3)137(4)105(3)43(3)18(2)-9(3)
C28129(4)125(4)132(4)55(3)28(3)4(3)
C18142(4)125(4)107(4)28(3)26(3)-6(3)
C17134(4)142(4)99(3)43(3)17(3)-14(3)
C888(2)133(3)88(2)52(2)16.8(18)6(2)
C486(2)121(3)84(2)39(2)7.2(17)-7.7(19)
C998(3)127(3)100(3)46(3)18(2)-15(2)
C1BA89(2)128(3)88(2)44(2)6.2(18)-16(2)
C1086(2)128(3)92(3)51(2)16.1(18)1.7(19)
C1193(2)134(3)90(3)56(2)8.2(19)6(2)
C12126(3)145(4)93(3)32(3)20(2)-18(3)
C13114(3)164(4)94(3)54(3)-4(2)-6(3)
F15161(4)122(4)106(3)29(2)30(3)-4(3)
F16177(5)170(5)88(3)45(3)0(3)-3(3)
C19125(3)129(4)92(3)34(3)13(2)-21(3)
C21134(4)153(4)83(3)43(3)7(2)-18(3)
F22191(5)155(4)90(3)16(3)21(3)-9(3)
C23116(3)118(3)121(3)45(3)6(2)-9(2)
F24199(6)149(5)90(4)39(3)7(3)-5(4)
F25190(6)133(5)157(5)52(3)37(4)7(3)
C2696(3)131(3)84(2)47(2)3(2)-8(2)
C27119(3)128(4)90(3)44(2)3(2)4(2)
C29105(3)118(3)88(3)43(2)-2(2)-17(2)
C30148(4)163(5)154(5)90(4)44(3)7(3)
C31144(5)139(5)127(4)58(4)21(4)-8(4)
C32212(6)268(8)149(5)143(5)-6(4)-13(5)
F33259(9)142(5)112(5)26(4)42(4)3(4)
C34194(6)159(5)184(6)95(5)20(5)-14(4)
C35173(6)203(7)230(8)110(6)66(5)-16(5)
C36260(9)294(10)185(7)158(7)-25(6)-49(7)
C37346(12)136(5)167(7)37(5)57(7)16(6)
C38146(5)495(15)208(7)229(9)-25(5)-76(7)
C39430(20)116(6)228(13)72(7)82(13)23(10)
C40230(11)680(30)510(20)450(20)158(13)71(13)
C41375(14)347(15)222(10)144(9)-105(9)-77(11)
C43429(19)420(20)343(16)236(15)-156(14)-101(15)
C47590(30)171(11)243(16)82(10)141(19)130(17)
C39A430(20)116(6)228(13)72(7)82(13)23(10)
C47A590(30)171(11)243(16)82(10)141(19)130(17)
C31A144(5)139(5)127(4)58(4)21(4)-8(4)
C6340(20)500(30)590(40)210(30)-170(20)-40(17)
C28A129(4)125(4)132(4)55(3)28(3)4(3)
C18A142(4)125(4)107(4)28(3)26(3)-6(3)
C17A134(4)142(4)99(3)43(3)17(3)-14(3)
C19A125(3)129(4)92(3)34(3)13(2)-21(3)
C12A126(3)145(4)93(3)32(3)20(2)-18(3)
C21A134(4)153(4)83(3)43(3)7(2)-18(3)

 

Table 4 Bond Lengths for 06F.
AtomAtomLength/Å AtomAtomLength/Å
O0AAC5AA1.434(4) C20C101.535(5)
O0AAC261.410(5) C14C281.3900
O2C71.265(5) C28C181.3900
O3C9AA1.433(5) C28F251.401(6)
O3C271.421(5) C18F331.409(6)
O8AAC291.235(5) C8C111.453(6)
O5C261.235(5) C4C1BA1.418(6)
N1C71.394(6) C4C261.541(6)
N1C7AA1.453(5) C9C191.411(6)
N1C131.505(6) C1BAC291.546(6)
C1AAC3AA11.442(5) C11C9AA21.386(6)
C1AAC5AA1.389(6) C12C191.419(7)
C2AAC6AA1.432(6) C13C321.586(8)
C2AAC211.412(7) F16C211.375(6)
C3AAC1AA11.442(5) C23C301.577(7)
C3AAC5AA1.435(6) C30C311.504(9)
C3AAC41.517(5) C30C341.601(9)
O4AAC271.240(6) C30C31A1.45(2)
C6AAC91.446(6) C31C351.584(9)
C6AAC1BA1.523(6) C32C361.619(10)
C9AAC81.437(6) C32C381.520(10)
C9AAC1121.386(6) C34C371.524(10)
C0BAC81.503(6) C35C31A1.733(19)
C0BAC101.416(6) C36C411.538(13)
C0BAC271.541(7) C37C391.595(16)
N6C91.432(5) C37C39A1.546(19)
N6C231.502(6) C38C401.542(14)
N6C291.413(6) C39C471.56(2)
C7C101.557(6) C41C431.533(11)
C7AAC201.3900 C43C61.499(14)
C7AAC171.3900 C39AC47A1.532(19)
C20C141.3900    

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

 

Table 5 Bond Angles for 06F.
AtomAtomAtomAngle/˚ AtomAtomAtomAngle/˚
C26O0AAC5AA107.9(3) C1BAC4C26124.0(4)
C27O3C9AA107.6(3) N6C9C6AA111.0(4)
C7N1C7AA109.0(3) C19C9C6AA120.3(4)
C7N1C13122.5(4) C19C9N6128.6(5)
C7AAN1C13128.2(3) C6AAC1BAC29105.1(4)
C5AAC1AAC3AA1116.5(4) C4C1BAC6AA131.8(4)
C21C2AAC6AA118.8(5) C4C1BAC29123.0(4)
C1AA1C3AAC4136.4(4) C0BAC10C7122.3(4)
C5AAC3AAC1AA1116.7(4) C0BAC10C20133.8(4)
C5AAC3AAC4106.9(3) C20C10C7103.9(3)
O0AAC5AAC3AA111.8(3) C9AA2C11C8117.0(4)
C1AAC5AAO0AA121.4(4) N1C13C32114.8(4)
C1AAC5AAC3AA126.8(4) C9C19C12120.0(5)
C2AAC6AAC9119.5(4) F16C21C2AA119.1(6)
C2AAC6AAC1BA134.3(4) N6C23C30114.6(4)
C9C6AAC1BA106.2(4) O0AAC26C4109.7(3)
O3C9AAC8112.0(4) O5C26O0AA119.2(4)
C112C9AAO3121.1(4) O5C26C4131.1(4)
C112C9AAC8126.9(4) O3C27C0BA109.2(4)
C8C0BAC27104.2(3) O4AAC27O3119.5(4)
C10C0BAC8132.5(4) O4AAC27C0BA131.3(4)
C10C0BAC27123.2(4) O8AAC29N6123.2(4)
C9N6C23127.1(4) O8AAC29C1BA129.3(4)
C29N6C9110.1(4) N6C29C1BA107.5(3)
C29N6C23122.8(4) C23C30C34107.9(5)
O2C7N1124.3(4) C31C30C23115.9(5)
O2C7C10127.6(4) C31C30C34114.1(5)
N1C7C10107.8(4) C31AC30C23122.9(8)
C20C7AAN1112.3(2) C31AC30C34127.1(9)
C20C7AAC17120.0 C30C31C35114.2(6)
C17C7AAN1127.7(2) C13C32C36105.8(6)
C7AAC20C10106.7(2) C38C32C13115.5(6)
C14C20C7AA120.0 C38C32C36111.0(7)
C14C20C10133.2(2) C37C34C30114.4(6)
C20C14C28120.0 C41C36C32120.3(8)
C14C28F25120.9(3) C34C37C39115.8(8)
C18C28C14120.0 C34C37C39A107.2(13)
C18C28F25119.1(3) C32C38C40108.9(11)
C28C18F33121.1(4) C47C39C37117.0(11)
C9AAC8C0BA107.0(4) C43C41C36110.5(11)
C9AAC8C11116.0(4) C6C43C41118.0(12)
C11C8C0BA136.9(4) C47AC39AC37109.9(18)
C3AAC4C26103.5(4) C30C31AC35108.6(12)
C1BAC4C3AA132.4(4)     

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

 

Table 6 Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 06F.
AtomxyzU(eq)
H1AA455965274834120
H2AB166623811850135
H2AA166623811850135
H1487847663020139
H14A87847663020139
H1761711010759151
H11860152033872123
H121970-474790149
H13A497636491553150
H13B463025861002150
H193279-6641915142
H23A56292384002144
H23B5520-3843170144
H302496-10393114173
H30A3279-4304129173
H31A17682724098162
H31B2666-2434637162
H3273742814549238
H34A5292-14054141207
H34B3385-20343922207
H35A-519-10933524287
H35B-548-7054376287
H35C397-16324044287
H35D284-16623999287
H35E-1116-9453882287
H35F643-5684494287
H36A49694268483286
H36B62573917-90286
H37A5560-19522861262
H37B3772-26602707262
H37C5999-25643219262
H37D5024-20062722262
H38A893441021687320
H38B795848151335320
H39A6857-28653692303
H39B5217-36613268303
H40A102783503605599
H40B109034613997599
H40C93734262289599
H41A44122447-650390
H41B31832714-38390
H43A24804085-437483
H43B34303632-1114483
H47A6426-39362156480
H47B7863-41022772480
H47C8073-31382583480
H39C2969-34393101303
H39D2274-29982480303
H47D4204-38261729480
H47E3174-45931990480
H47F5193-41592369480
H31C914-12232883162
H31D1126-1133344162
H6A11312426-1640750
H6B1933374-1377750
H6C2942665-913750
H28A8298-5871962151
H18A6992-465831153
H21A11391032773150

 

Table 7 Atomic Occupancy for 06F.
AtomOccupancy AtomOccupancy AtomOccupancy
H2AB0.590(8) H2AA0.410(8) H140.410(8)
H14A0.590(8) C280.410(8) C180.410(8)
C170.590(8) H170.590(8) C120.410(8)
H120.410(8) F150.590(8) F160.590(8)
C190.410(8) H190.410(8) C210.590(8)
F220.590(8) F240.520(11) F250.566(12)
H300.730(6) H30A0.270(6) C310.730(6)
H31A0.730(6) H31B0.730(6) F330.537(13)
H35A0.730(6) H35B0.730(6) H35C0.730(6)
H35D0.270(6) H35E0.270(6) H35F0.270(6)
H37A0.410(8) H37B0.410(8) H37C0.590(8)
H37D0.590(8) C390.730(6) H39A0.730(6)
H39B0.730(6) C470.730(6) H47A0.24(8)
H47B0.24(8) H47C0.24(8) C39A0.270(6)
H39C0.270(6) H39D0.270(6) C47A0.270(6)
H47D0.76(8) H47E0.76(8) H47F0.76(8)
C31A0.270(6) H31C0.270(6) H31D0.270(6)
C28A0.590(8) H28A0.590(8) C18A0.590(8)
H18A0.590(8) C17A0.410(8) C19A0.590(8)
C12A0.590(8) C21A0.410(8) H21A0.410(8)

Experimental

Single crystals of C42H41F3.37N2O6 [06F] 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 [06F]

Crystal Data for C42H41F3.37N2O6 (=733.70 g/mol): triclinic, space group P-1 (no. 2), a = 7.442 Å, b = 14.635 Å, c = 19.312 Å, α = 108.27°, β = 98.49°, γ = 93.69°, = 1961.7 Å3, Z = 2, T = 293(2) K, μ(Synchrotron Monochromator X-ray) = 0.088 mm-1, Dcalc = 1.242 g/cm3, 20424 reflections measured (2.86° ≤ 2Θ ≤ 46.64°), 5738 unique (Rint = 0.0902, Rsigma = 0.0574) which were used in all calculations. The final R1 was 0.1133 (I > 2σ(I)) and wR2 was 0.3671 (all data).

Refinement model description

Number of restraints - 49, 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
{C28A, C28}
{C18A, C18}
{C17, C17A}
{C19, C19A}
{C12, C12A}
{C21A, C21}
3. Restrained distances
C41-C43
1.55 with sigma of 0.02
C37-C39A
1.55 with sigma of 0.02
C39A-C47A
1.55 with sigma of 0.02
C38-C32
1.55 with sigma of 0.02
C7AA-C20
1.395 with sigma of 0.02
C43-C41 = C6-C43
1.55 with sigma of 0.02
C41-C6
2.5 with sigma of 0.02
C20-C10
1.395 with sigma of 0.02
C47A-C37
2.5 with sigma of 0.02
C7-C10
1.4 with sigma of 0.02
4. Rigid bond restraints
C41, C36, C43, C6
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
C32, C38, C40
with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C36 ≈ C41 ≈ C43 ≈ C6: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C40 ≈ C38 ≈ C32: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C39) = Uanis(C39A)
Uanis(C47) = Uanis(C47A)
Uanis(C31) = Uanis(C31A)
Uanis(C18) = Uanis(C18A)
Uanis(C18A) = Uanis(C18)
Uanis(C17) = Uanis(C17A)
Uanis(C19) = Uanis(C19A)
Uanis(C12) = Uanis(C12A)
Uanis(C21) = Uanis(C21A)
Uanis(C21A) = Uanis(C21)
Uanis(C28) = Uanis(C28A)
Uanis(C28A) = Uanis(C28)
6. Others
Sof(H2AB)=Sof(H14A)=Sof(C17)=Sof(H17)=Sof(F15)=Sof(F16)=Sof(C21)=Sof(F22)=
Sof(H37C)=Sof(H37D)=Sof(C28A)=Sof(H28A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
Sof(C12A)=1-FVAR(1)
Sof(H2AA)=Sof(H14)=Sof(C28)=Sof(C18)=Sof(C12)=Sof(H12)=Sof(C19)=Sof(H19)=
Sof(H37A)=Sof(H37B)=Sof(C17A)=Sof(C21A)=Sof(H21A)=FVAR(1)
Sof(H47D)=Sof(H47E)=Sof(H47F)=1-FVAR(2)
Sof(H47A)=Sof(H47B)=Sof(H47C)=FVAR(2)
Sof(H30A)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C39A)=Sof(H39C)=Sof(H39D)=
Sof(C47A)=Sof(C31A)=Sof(H31C)=Sof(H31D)=1-FVAR(3)
Sof(H30)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C39)=
Sof(H39A)=Sof(H39B)=Sof(C47)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
C30(H30), C30(H30A), C32(H32)
7.b Secondary CH2 refined with riding coordinates:
C13(H13A,H13B), C23(H23A,H23B), C31(H31A,H31B), C34(H34A,H34B), C36(H36A,
H36B), C37(H37A,H37B), C37(H37C,H37D), C38(H38A,H38B), C39(H39A,H39B),
C41(H41A,H41B), C43(H43A,H43B), C39A(H39C,H39D), C31A(H31C,H31D)
7.c Me refined with riding coordinates:
C35(H35A,H35B,H35C), C35(H35D,H35E,H35F), C40(H40A,H40B,H40C), C47(H47A,H47B,
H47C), C47A(H47D,H47E,H47F), C6(H6A,H6B,H6C)
7.d Aromatic/amide H refined with riding coordinates:
C1AA(H1AA), C2AA(H2AB), C2AA(H2AA), C14(H14), C14(H14A), C17(H17), C11(H11),
C12(H12), C19(H19), C28A(H28A), C18A(H18A), C21A(H21A)
7.e Fitted hexagon refined as free rotating group:
C7AA(C20,C14,C28,C18,C17)

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