3F-decomposition

Table 1 Crystal data and structure refinement for 3F-decomposition.
Identification code 3F-decomposition
Empirical formula C42H41.48F0.52N2O6
Formula weight 680.07
Temperature/K 180
Crystal system trigonal
Space group R-3
a/Å 37.4781(16)
b/Å 37.4781(16)
c/Å 6.4871(3)
α/° 90
β/° 90
γ/° 120
Volume/Å3 7891.1(8)
Z 9
ρcalcg/cm3 1.288
μ/mm‑1 0.711
F(000) 3241.0
Crystal size/mm3 0.15 × 0.1 × 0.1
Radiation CuKα (λ = 1.54178)
2Θ range for data collection/° 8.172 to 148.036
Index ranges -43 ≤ h ≤ 46, -45 ≤ k ≤ 43, -8 ≤ l ≤ 3
Reflections collected 10803
Independent reflections 3478 [Rint = 0.0284, Rsigma = 0.0262]
Data/restraints/parameters 3478/14/255
Goodness-of-fit on F2 1.032
Final R indexes [I>=2σ (I)] R1 = 0.0819, wR2 = 0.2468
Final R indexes [all data] R1 = 0.1046, wR2 = 0.2761
Largest diff. peak/hole / e Å-3 0.48/-0.32

 

Table 2 Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 3F-decomposition. Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.
AtomxyzU(eq)
C13753.6(10)4273.5(11)36(5)67.7(8)
C1'3753.6(10)4273.5(11)36(5)67.7(8)
F13709(7)4522(7)-1310(40)83(6)
C23722.5(10)3907.4(12)-589(5)73.5(9)
C2'3722.5(10)3907.4(12)-589(5)73.5(9)
F23604(7)3818(7)-2350(40)83(6)
C33906.0(12)3734.8(11)532(6)78.6(10)
C3'3906.0(12)3734.8(11)532(6)78.6(10)
F33866(7)3409(7)170(40)83(6)
C44129.7(10)3915.6(10)2328(5)68.7(8)
C54163.7(8)4284.4(9)2994(4)56.0(7)
C63974.3(9)4457.3(10)1807(4)60.4(7)
N14054.0(9)4833.1(9)2659(4)67.8(7)
C74298.6(10)4924.7(10)4359(5)66.3(8)
C84370.2(8)4565.8(9)4726(4)55.2(7)
C94591.9(8)4552.6(8)6375(4)53.0(7)
C104685.3(10)4213.3(9)6726(5)62.9(8)
O14919.9(7)4293.1(6)8462(3)67.3(6)
C114972.4(9)4655.4(8)9324(4)54.3(7)
C124785.9(8)4828.0(8)8142(4)50.7(6)
C134817.8(9)5194.4(8)8869(4)55.3(7)
O24595.2(9)3904.7(7)5751(4)84.5(8)
O34432.4(10)5245.1(8)5321(4)92.2(9)
C143909.1(18)5082(3)1770(20)80(2)
C153453.3(17)4944(2)2255(7)92.0(16)
C163369(2)4948(3)4589(8)107(2)
C172905(3)4780(6)5020(20)116(4)
C183284(3)5133(3)685(13)145(3)
C193509(5)5609(3)650(30)240(4)
C203253(5)5699(4)-930(30)240(4)
C213479(5)6173(4)-640(30)240(4)
C14'3975(6)5188(9)1900(60)80(2)
C15'3608(4)5156(4)3150(20)92.0(16)
C16'3244(4)4724(4)3720(30)107(2)
C17'2945(8)4718(16)5380(50)116(4)
C18'3478(8)5439(7)2040(30)145(3)
C19'3459(13)5465(9)-340(30)240(4)
C20'3432(11)5858(8)-770(60)240(4)
C21'3198(10)5860(10)-2740(50)240(4)

 

Table 3 Anisotropic Displacement Parameters (Å2×103) for 3F-decomposition. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
AtomU11U22U33U23U13U12
C160.6(17)81(2)53.1(16)-4.0(14)-2.7(13)29.5(16)
C1'60.6(17)81(2)53.1(16)-4.0(14)-2.7(13)29.5(16)
F185(10)78(10)74(9)-42(7)-31(7)33(7)
C265.1(19)82(2)58.2(18)-15.7(16)-6.1(14)25.8(17)
C2'65.1(19)82(2)58.2(18)-15.7(16)-6.1(14)25.8(17)
F285(10)78(10)74(9)-42(7)-31(7)33(7)
C383(2)69(2)74(2)-23.4(16)-13.2(17)30.4(18)
C3'83(2)69(2)74(2)-23.4(16)-13.2(17)30.4(18)
F385(10)78(10)74(9)-42(7)-31(7)33(7)
C470.3(19)61.3(17)61.4(17)-10.0(14)-5.0(14)23.1(15)
C546.5(13)54.7(15)49.7(14)-1.2(11)4.6(11)12.6(11)
C652.2(15)67.6(17)50.1(14)-3.1(12)2.8(11)21.5(13)
N171.7(16)68.7(16)59.2(14)-6.7(12)-12.0(12)32.4(13)
C769.4(18)57.8(17)64.0(17)-3.7(13)-10.6(14)26.0(15)
C850.4(14)51.0(14)51.8(14)0.8(11)3.2(11)16.1(12)
C951.7(14)45.2(13)50.3(14)0.8(10)4.0(11)15.3(11)
C1074.1(19)49.1(15)56.4(16)-3.0(12)-5.9(13)24.0(14)
O191.1(15)55.2(11)58.4(12)-10.6(9)-13.7(10)38.7(11)
C1159.8(15)45.5(13)50.8(14)-1.8(10)2.1(11)21.2(12)
C1248.0(13)46.6(13)46.7(13)0.6(10)3.8(10)15.6(11)
C1358.9(15)51.3(14)51.7(14)-1.0(11)-2.1(12)24.6(12)
O2117(2)58.0(13)78.0(15)-16.9(11)-24.9(14)42.9(14)
O3123(2)61.8(14)92.0(17)-18.4(12)-44.9(16)46.4(15)
C1492(4)56(7)80(3)-8(4)-28(4)28(4)
C1598(4)99(4)92(4)-27(3)-37(3)60(4)
C1689(4)128(6)97(5)-39(4)-6(3)49(4)
C1792(4)116(8)126(7)-6(6)4(4)43(4)
C18163(8)185(10)132(7)4(6)-7(6)121(8)
C19233(9)187(7)318(10)61(8)-56(8)118(7)
C20233(9)187(7)318(10)61(8)-56(8)118(7)
C21233(9)187(7)318(10)61(8)-56(8)118(7)
C14'92(4)56(7)80(3)-8(4)-28(4)28(4)
C15'98(4)99(4)92(4)-27(3)-37(3)60(4)
C16'89(4)128(6)97(5)-39(4)-6(3)49(4)
C17'92(4)116(8)126(7)-6(6)4(4)43(4)
C18'163(8)185(10)132(7)4(6)-7(6)121(8)
C19'233(9)187(7)318(10)61(8)-56(8)118(7)
C20'233(9)187(7)318(10)61(8)-56(8)118(7)
C21'233(9)187(7)318(10)61(8)-56(8)118(7)

 

Table 4 Bond Lengths for 3F-decomposition.
AtomAtomLength/Å AtomAtomLength/Å
C1C21.379(5) C11C121.395(4)
C1C61.382(4) C11C1311.366(4)
C2C31.366(5) C12C131.399(4)
C3C41.397(5) C13C1111.366(4)
C4C51.392(4) C14C151.550(2)
C5C61.406(4) C15C161.549(2)
C5C81.469(4) C15C181.547(2)
C6N11.399(4) C16C171.550(2)
N1C71.364(4) C18C191.547(2)
N1C141.417(15) C19C201.551(2)
N1C14'1.58(4) C20C211.549(2)
C7C81.516(4) C14'C15'1.550(2)
C7O31.217(4) C15'C16'1.550(2)
C8C91.371(4) C15'C18'1.550(2)
C9C101.495(4) C16'C17'1.550(2)
C9C121.469(4) C18'C19'1.549(2)
C10O11.367(4) C19'C20'1.551(2)
C10O21.209(4) C20'C21'1.550(2)
O1C111.389(3)    

11-X,1-Y,2-Z

 

Table 5 Bond Angles for 3F-decomposition.
AtomAtomAtomAngle/˚ AtomAtomAtomAngle/˚
C2C1C6118.2(3) O2C10O1118.8(3)
C3C2C1120.2(3) C10O1C11107.8(2)
C2C3C4122.4(3) O1C11C12111.9(2)
C5C4C3118.4(3) C131C11O1121.3(3)
C4C5C6118.1(3) C131C11C12126.8(3)
C4C5C8134.8(3) C11C12C9106.8(2)
C6C5C8107.1(3) C11C12C13116.9(2)
C1C6C5122.7(3) C13C12C9136.2(3)
C1C6N1127.1(3) C111C13C12116.3(3)
N1C6C5110.2(2) N1C14C15114.7(8)
C6N1C14122.8(5) C16C15C14113.2(7)
C6N1C14'133.7(12) C18C15C14110.4(8)
C7N1C6110.6(3) C18C15C16120.4(6)
C7N1C14126.6(5) C15C16C17111.3(7)
C7N1C14'115.1(12) C19C18C15115.3(7)
N1C7C8107.4(3) C18C19C20102.9(8)
O3C7N1123.8(3) C21C20C1997.2(9)
O3C7C8128.8(3) C15'C14'N1108(2)
C5C8C7104.7(2) C14'C15'C16'119.2(14)
C9C8C5133.0(3) C18'C15'C14'105.9(19)
C9C8C7122.3(3) C18'C15'C16'114.3(14)
C8C9C10123.6(3) C17'C16'C15'116(2)
C8C9C12132.8(3) C19'C18'C15'123.2(16)
C12C9C10103.6(2) C18'C19'C20'105.6(17)
O1C10C9109.8(2) C21'C20'C19'117(2)
O2C10C9131.4(3)     

11-X,1-Y,2-Z

 

Table 6 Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 3F-decomposition.
AtomxyzU(eq)
H136294394-71581
H235763778-177788
H3388134888294
H1347035328816266
H14A3941508328296
H14B40815363224696
H15330646501907110
H16A352752285104128
H16B345947815319128
H17A286347956466174
H17B275044984571174
H17C281449424275174
H18A32995036-682174
H18B29955031989174
H19A37925724195288
H19B350657191995288
H20A32805621-2324288
H20B29645569-556288
H21A33976294-1707360
H21B37716281-708360
H21C34096237680360
H14C42195455212996
H14D3911515844496
H15'372552914474110
H16C308845982477128
H16D335745564198128
H17D306947566721174
H17E269344595341174
H17F288749375122174
H18C320553632551174
H18D366257172525174
H19C32195223-881288
H19D37045487-964288
H20C33015905402288
H20D37116090-857288
H21D31826107-2774360
H21E29255625-2727360
H21F33435849-3939360

 

Table 7 Atomic Occupancy for 3F-decomposition.
AtomOccupancy AtomOccupancy AtomOccupancy
C10.914(5) H10.914(5) C1'0.086(5)
F10.086(5) C20.914(5) H20.914(5)
C2'0.086(5) F20.086(5) C30.914(5)
H30.914(5) C3'0.086(5) F30.086(5)
C140.686(4) H14A0.686(4) H14B0.686(4)
C150.686(4) H150.686(4) C160.686(4)
H16A0.686(4) H16B0.686(4) C170.686(4)
H17A0.686(4) H17B0.686(4) H17C0.686(4)
C180.686(4) H18A0.686(4) H18B0.686(4)
C190.686(4) H19A0.686(4) H19B0.686(4)
C200.686(4) H20A0.686(4) H20B0.686(4)
C210.686(4) H21A0.686(4) H21B0.686(4)
H21C0.686(4) C14'0.314(4) H14C0.314(4)
H14D0.314(4) C15'0.314(4) H15'0.314(4)
C16'0.314(4) H16C0.314(4) H16D0.314(4)
C17'0.314(4) H17D0.314(4) H17E0.314(4)
H17F0.314(4) C18'0.314(4) H18C0.314(4)
H18D0.314(4) C19'0.314(4) H19C0.314(4)
H19D0.314(4) C20'0.314(4) H20C0.314(4)
H20D0.314(4) C21'0.314(4) H21D0.314(4)
H21E0.314(4) H21F0.314(4)   

Experimental

Single crystals of C42H41.48F0.52N2O6 [3F-decomposition] were []. A suitable crystal was selected and [] on a diffractometer. The crystal was kept at 180 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-decomposition]

Crystal Data for C42H41.48F0.52N2O6 (=680.07 g/mol): trigonal, space group R-3 (no. 148), a = 37.4781(16) Å, c = 6.4871(3) Å, = 7891.1(8) Å3, Z = 9, T = 180 K, μ(CuKα) = 0.711 mm-1, Dcalc = 1.288 g/cm3, 10803 reflections measured (8.172° ≤ 2Θ ≤ 148.036°), 3478 unique (Rint = 0.0284, Rsigma = 0.0262) which were used in all calculations. The final R1 was 0.0819 (I > 2σ(I)) and wR2 was 0.2761 (all data).

Refinement model description

Number of restraints - 14, number of constraints - unknown.

Details:

1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2. Shared sites
{C1, C1'}
{C2, C2'}
{C3, C3'}
3. Restrained distances
C14-C15 = C15-C16 = C16-C17 = C15-C18 = C18-C19 = C19-C20 = C20-C21
1.55 with sigma of 0.002
C14'-C15' = C15'-C16' = C16'-C17'
1.55 with sigma of 0.002
C15'-C18' = C18'-C19' = C19'-C20' = C20'-C21'
1.55 with sigma of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C1')
Uanis(C2) = Uanis(C2')
Uanis(C3) = Uanis(C3')
Uanis(C14) = Uanis(C14')
Uanis(F1) = Uanis(F2) = Uanis(F3)
Uanis(C15) = Uanis(C15')
Uanis(C16) = Uanis(C16')
Uanis(C17) = Uanis(C17')
Uanis(C18) = Uanis(C18')
Uanis(C19) = Uanis(C19') = Uanis(C20) = Uanis(C20') = Uanis(C21) = Uanis(C21')
5. Others
Sof(C1')=Sof(F1)=Sof(C2')=Sof(F2)=Sof(C3')=Sof(F3)=1-FVAR(1)
Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=FVAR(1)
Sof(C14')=Sof(H14C)=Sof(H14D)=Sof(C15')=Sof(H15')=Sof(C16')=Sof(H16C)=
Sof(H16D)=Sof(C17')=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18')=Sof(H18C)=
Sof(H18D)=Sof(C19')=Sof(H19C)=Sof(H19D)=Sof(C20')=Sof(H20C)=Sof(H20D)=
Sof(C21')=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(2)
Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=
Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=
Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=
Sof(H21C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
C15(H15), C15'(H15')
6.b Secondary CH2 refined with riding coordinates:
C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
H20B), C14'(H14C,H14D), C16'(H16C,H16D), C18'(H18C,H18D), C19'(H19C,H19D),
C20'(H20C,H20D)
6.c Me refined with riding coordinates:
C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C17'(H17D,H17E,H17F), C21'(H21D,
H21E,H21F)
6.d Aromatic/amide H refined with riding coordinates:
C1(H1), C2(H2), C3(H3), C13(H13)

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