3193_twin1_hklf4

Table 1 Crystal data and structure refinement for 3193_twin1_hklf4.
Identification code 3193_twin1_hklf4
Empirical formula C16H26ClFeNSi
Formula weight 351.77
Temperature/K 173.15
Crystal system triclinic
Space group P-1
a/Å 10.4038(9)
b/Å 11.5162(11)
c/Å 16.0747(16)
α/° 71.308(9)
β/° 81.097(8)
γ/° 89.850(7)
Volume/Å3 1800.1(3)
Z 4
ρcalcg/cm3 1.298
μ/mm‑1 1.044
F(000) 744.0
Crystal size/mm3 0.107 × 0.105 × 0.01
Radiation MoKα (λ = 0.71073)
2Θ range for data collection/° 4.426 to 52
Index ranges -12 ≤ h ≤ 12, -14 ≤ k ≤ 14, -19 ≤ l ≤ 19
Reflections collected 8830
Independent reflections 8830 [Rint = N/A, Rsigma = 0.1178]
Data/restraints/parameters 8830/60/372
Goodness-of-fit on F2 0.990
Final R indexes [I>=2σ (I)] R1 = 0.0621, wR2 = 0.1572
Final R indexes [all data] R1 = 0.1101, wR2 = 0.1843
Largest diff. peak/hole / e Å-3 0.78/-0.56

 

Table 2 Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 3193_twin1_hklf4. Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.
AtomxyzU(eq)
Fe11824.6(10)4660.0(9)1662.3(7)30.8(3)
Si1-1335(2)5716.3(17)2051.8(13)25.6(5)
N1428(5)2805(5)4418(4)24.2(13)
C1-173(6)4462(6)2097(4)22.7(15)
C2526(6)3810(6)2795(4)23.5(16)
C31291(7)2937(6)2497(4)26.3(16)
C41098(7)3037(6)1623(4)28.6(17)
C5202(7)3972(5)1384(4)24.9(16)
C62406(9)6477(7)1145(6)55(3)
C72918(13)5909(11)1904(8)84(4)
C83695(10)4987(12)1745(10)99(5)
C93616(10)4964(9)883(8)74(3)
C102819(9)5877(8)532(6)56(3)
C11523(7)3988(5)3680(4)26.5(16)
C12-773(7)2030(6)4508(5)35.0(19)
C13502(6)3025(6)5269(4)26.4(16)
C14-1576(8)6391(7)875(5)42(2)
C15-716(8)6934(7)2441(5)47(2)
C16-2917(7)5057(6)2786(5)41(2)
Fe2-5248.3(10)9660.4(10)1799.9(7)32.1(3)
Si2-2201(2)10617.5(17)2124.4(13)27.7(5)
N2-5159(5)7754(5)4540(3)20.8(12)
C17-3453(7)9400(5)2206(4)23.6(15)
C18-4490(7)8764(6)2912(5)28.6(17)
C19-5154(7)7918(6)2623(4)30.1(17)
C20-4557(7)8018(6)1759(4)26.9(16)
C21-3529(7)8923(6)1486(4)25.5(16)
C22-5481(11)11510(9)1200(8)72(3)
C23-6189(12)11159(10)1997(8)79(3)
C24-7045(10)10263(10)2105(7)71(3)
C25-6893(11)9936(9)1260(11)115(6)
C26-5868(11)10842(9)718(6)67(3)
C27-4813(7)8947(6)3796(4)27.3(16)
C28-4056(8)6938(7)4642(5)40(2)
C29-5653(7)7975(6)5379(4)30.2(17)
C30-1306(8)11109(7)956(5)44(2)
C31-1052(8)10008(6)2892(5)39(2)
C32-2934(8)11966(6)2389(5)44(2)
Cl12496.4(17)898.3(15)4466.1(12)29.0(4)
Cl2-7267.3(17)5903.6(15)4522.9(12)31.0(4)

 

Table 3 Anisotropic Displacement Parameters (Å2×103) for 3193_twin1_hklf4. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
AtomU11U22U33U23U13U12
Fe126.9(6)27.8(6)35.3(6)-8.7(5)-0.7(5)-4.0(5)
Si133.6(12)19(1)24.7(11)-6.9(9)-6.4(9)7.7(9)
N120(3)24(3)34(3)-14(3)-10(3)0(3)
C119(4)20(3)29(4)-9(3)1(3)-1(3)
C227(4)20(3)29(4)-10(3)-17(3)-2(3)
C332(4)20(4)29(4)-7(3)-14(3)9(3)
C435(4)21(4)32(4)-13(3)0(3)1(3)
C534(4)18(3)26(4)-11(3)-7(3)1(3)
C663(7)30(5)62(6)-9(5)9(5)-23(5)
C790(9)94(9)71(8)-39(7)3(7)-68(8)
C830(6)107(11)112(11)40(9)-28(7)-35(6)
C940(6)62(7)90(9)-4(7)31(6)-8(5)
C1063(7)51(6)43(5)-15(5)28(5)-29(5)
C1138(4)16(3)24(4)-3(3)-9(3)3(3)
C1233(5)31(4)41(5)-18(4)7(4)-5(4)
C1320(4)29(4)31(4)-10(3)-4(3)7(3)
C1449(5)40(4)34(5)-7(4)-10(4)28(4)
C1567(6)40(5)42(5)-20(4)-20(5)8(5)
C1637(5)24(4)53(5)-7(4)0(4)8(4)
Fe229.8(6)38.8(6)30.5(6)-13.6(5)-8.0(5)11.1(5)
Si234.9(13)20.7(10)27.2(11)-9.0(9)-0.8(9)-4.3(9)
N220(3)21(3)24(3)-12(2)-2(2)-3(2)
C1730(4)16(3)26(4)-10(3)-3(3)8(3)
C1830(4)21(4)41(4)-16(3)-11(3)2(3)
C1937(5)19(4)30(4)-5(3)2(3)-5(3)
C2027(4)25(4)31(4)-11(3)-8(3)-3(3)
C2127(4)23(4)27(4)-11(3)0(3)7(3)
C2272(8)53(6)88(8)-12(6)-27(7)32(6)
C2383(9)66(7)99(9)-39(7)-27(7)48(7)
C2451(5)73(5)70(5)-1(4)-4(4)19(4)
C2573(8)56(7)268(18)-81(9)-129(10)39(6)
C26100(9)76(7)52(6)-38(6)-61(6)52(7)
C2724(4)24(4)35(4)-9(3)-8(3)3(3)
C2852(5)38(5)44(5)-22(4)-28(4)18(4)
C2935(5)23(4)32(4)-6(3)-7(3)-4(3)
C3058(6)35(4)34(5)-7(4)2(4)-21(4)
C3146(5)28(4)47(5)-16(4)-14(4)-5(4)
C3260(6)24(4)57(5)-23(4)-11(5)1(4)
Cl126.5(10)24.6(9)37.2(10)-11.7(8)-5.7(8)5.1(8)
Cl223.9(10)21.2(9)47.8(11)-11.6(8)-4.7(8)-1.3(8)

 

Table 4 Bond Lengths for 3193_twin1_hklf4.
AtomAtomLength/Å AtomAtomLength/Å
Fe1C12.076(7) Fe2C172.062(7)
Fe1C22.050(7) Fe2C182.033(7)
Fe1C32.028(6) Fe2C192.031(7)
Fe1C42.041(6) Fe2C202.040(7)
Fe1C52.036(6) Fe2C212.041(7)
Fe1C62.042(7) Fe2C222.068(9)
Fe1C72.005(8) Fe2C232.070(9)
Fe1C82.015(9) Fe2C242.036(10)
Fe1C92.040(9) Fe2C252.016(9)
Fe1C102.032(8) Fe2C262.029(8)
Si1C11.872(7) Si2C171.875(7)
Si1C141.858(7) Si2C301.870(7)
Si1C151.862(7) Si2C311.828(8)
Si1C161.874(7) Si2C321.868(7)
N1C111.484(8) N2C271.504(8)
N1C121.499(8) N2C281.476(8)
N1C131.482(7) N2C291.467(7)
C1C21.436(9) C17C181.442(9)
C1C51.435(8) C17C211.444(8)
C2C31.435(9) C18C191.427(8)
C2C111.500(8) C18C271.491(9)
C3C41.417(9) C19C201.400(9)
C4C51.420(9) C20C211.411(9)
C6C71.374(14) C22C231.313(13)
C6C101.392(10) C22C261.355(12)
C7C81.396(15) C23C241.315(14)
C8C91.410(15) C24C251.509(15)
C9C101.368(13) C25C261.456(16)

 

Table 5 Bond Angles for 3193_twin1_hklf4.
AtomAtomAtomAngle/˚ AtomAtomAtomAngle/˚
C2Fe1C140.7(2) C17Fe2C22110.2(4)
C3Fe1C168.8(3) C17Fe2C23115.0(4)
C3Fe1C241.2(2) C18Fe2C1741.2(3)
C3Fe1C440.8(2) C18Fe2C2068.4(3)
C3Fe1C567.9(3) C18Fe2C2168.9(3)
C3Fe1C6164.1(3) C18Fe2C22130.9(4)
C3Fe1C9118.6(4) C18Fe2C23108.4(4)
C3Fe1C10153.0(3) C18Fe2C24111.7(4)
C4Fe1C169.4(3) C19Fe2C1769.3(3)
C4Fe1C269.4(2) C19Fe2C1841.1(2)
C4Fe1C6154.9(3) C19Fe2C2040.2(2)
C5Fe1C140.8(2) C19Fe2C2168.4(3)
C5Fe1C268.3(2) C19Fe2C22168.3(4)
C5Fe1C440.8(3) C19Fe2C23131.8(4)
C5Fe1C6122.4(4) C19Fe2C24108.5(4)
C5Fe1C9125.3(4) C20Fe2C1768.8(2)
C6Fe1C1110.2(3) C20Fe2C2140.5(2)
C6Fe1C2127.7(3) C20Fe2C22151.3(4)
C7Fe1C1120.9(4) C20Fe2C23170.7(4)
C7Fe1C2108.3(4) C21Fe2C1741.2(2)
C7Fe1C3126.2(4) C21Fe2C22119.5(4)
C7Fe1C4162.4(5) C21Fe2C23147.7(4)
C7Fe1C5156.0(5) C22Fe2C2337.0(4)
C7Fe1C639.7(4) C24Fe2C17142.3(4)
C7Fe1C840.6(5) C24Fe2C20134.7(4)
C7Fe1C968.4(5) C24Fe2C21174.9(4)
C7Fe1C1067.3(4) C24Fe2C2264.3(4)
C8Fe1C1155.2(5) C24Fe2C2337.4(4)
C8Fe1C2119.9(4) C25Fe2C17173.3(5)
C8Fe1C3106.9(4) C25Fe2C18144.5(5)
C8Fe1C4124.3(5) C25Fe2C19113.2(4)
C8Fe1C5162.2(6) C25Fe2C20108.8(3)
C8Fe1C666.9(5) C25Fe2C21133.1(5)
C8Fe1C940.7(4) C25Fe2C2268.7(4)
C8Fe1C1066.7(4) C25Fe2C2368.4(4)
C9Fe1C1163.2(4) C25Fe2C2443.7(4)
C9Fe1C2154.1(4) C25Fe2C2642.2(5)
C9Fe1C4105.6(4) C26Fe2C17133.0(4)
C9Fe1C667.1(4) C26Fe2C18169.3(3)
C10Fe1C1128.1(4) C26Fe2C19149.6(4)
C10Fe1C2165.2(3) C26Fe2C20120.1(3)
C10Fe1C4119.3(3) C26Fe2C21112.7(4)
C10Fe1C5109.6(3) C26Fe2C2238.6(3)
C10Fe1C640.0(3) C26Fe2C2364.2(4)
C10Fe1C939.2(4) C26Fe2C2467.7(4)
C1Si1C16109.4(3) C30Si2C17106.5(3)
C14Si1C1107.1(3) C31Si2C17110.9(3)
C14Si1C15109.7(4) C31Si2C30109.2(4)
C14Si1C16110.5(4) C31Si2C32107.4(3)
C15Si1C1112.5(3) C32Si2C17112.8(3)
C15Si1C16107.6(4) C32Si2C30110.1(4)
C11N1C12113.3(5) C28N2C27112.3(5)
C13N1C11110.3(5) C29N2C27110.7(5)
C13N1C12110.2(5) C29N2C28110.9(5)
Si1C1Fe1127.1(3) Si2C17Fe2127.1(3)
C2C1Fe168.6(4) C18C17Fe268.3(4)
C2C1Si1129.8(5) C18C17Si2131.6(5)
C5C1Fe168.1(4) C18C17C21106.0(5)
C5C1Si1124.2(5) C21C17Fe268.6(4)
C5C1C2106.0(6) C21C17Si2122.4(5)
C1C2Fe170.6(4) C17C18Fe270.5(4)
C1C2C11128.2(6) C17C18C27126.1(5)
C3C2Fe168.6(4) C19C18Fe269.3(4)
C3C2C1107.8(5) C19C18C17108.3(6)
C3C2C11124.0(6) C19C18C27125.5(6)
C11C2Fe1125.1(4) C27C18Fe2126.2(5)
C2C3Fe170.2(4) C18C19Fe269.5(4)
C4C3Fe170.1(4) C20C19Fe270.2(4)
C4C3C2109.4(6) C20C19C18108.2(6)
C3C4Fe169.1(4) C19C20Fe269.5(4)
C3C4C5106.3(6) C19C20C21109.0(6)
C5C4Fe169.4(3) C21C20Fe269.8(4)
C1C5Fe171.1(4) C17C21Fe270.2(4)
C4C5Fe169.8(4) C20C21Fe269.7(4)
C4C5C1110.4(6) C20C21C17108.5(6)
C7C6Fe168.7(5) C23C22Fe271.5(6)
C7C6C10107.9(10) C23C22C26109.4(11)
C10C6Fe169.7(4) C26C22Fe269.1(5)
C6C7Fe171.6(5) C22C23Fe271.4(6)
C6C7C8107.6(10) C22C23C24112.3(11)
C8C7Fe170.1(5) C24C23Fe270.0(6)
C7C8Fe169.3(6) C23C24Fe272.7(6)
C7C8C9108.3(11) C23C24C25108.6(10)
C9C8Fe170.6(6) C25C24Fe267.4(5)
C8C9Fe168.7(5) C24C25Fe268.8(5)
C10C9Fe170.1(5) C26C25Fe269.4(5)
C10C9C8106.4(10) C26C25C2499.5(7)
C6C10Fe170.4(4) C22C26Fe272.3(5)
C9C10Fe170.7(5) C22C26C25110.1(10)
C9C10C6109.7(10) C25C26Fe268.4(5)
N1C11C2112.3(5) C18C27N2112.1(5)

 

Table 6 Hydrogen Bonds for 3193_twin1_hklf4.
DHAd(D-H)/Åd(H-A)/Åd(D-A)/ÅD-H-A/°
N1H1Cl11.002.113.062(6)159.2
N2H2Cl21.002.123.071(5)158.0

 

Table 7 Torsion Angles for 3193_twin1_hklf4.
ABCDAngle/˚ ABCDAngle/˚
Fe1C1C2C3-58.7(4) Fe2C17C18C1959.2(5)
Fe1C1C2C11119.9(6) Fe2C17C18C27-121.1(7)
Fe1C1C5C458.9(5) Fe2C17C21C20-59.4(5)
Fe1C2C3C4-59.3(5) Fe2C18C19C2059.8(5)
Fe1C2C11N1-131.5(5) Fe2C18C27N2129.5(5)
Fe1C3C4C5-59.8(4) Fe2C19C20C2158.8(5)
Fe1C4C5C1-59.6(4) Fe2C20C21C1759.7(5)
Fe1C6C7C861.2(6) Fe2C22C23C24-58.1(8)
Fe1C6C10C9-60.0(6) Fe2C22C26C2558.1(6)
Fe1C7C8C960.1(7) Fe2C23C24C25-58.1(7)
Fe1C8C9C1060.2(6) Fe2C24C25C26-63.4(6)
Fe1C9C10C659.8(6) Fe2C25C26C22-60.4(7)
Si1C1C2Fe1-121.2(5) Si2C17C18Fe2121.0(6)
Si1C1C2C3-179.9(5) Si2C17C18C19-179.8(5)
Si1C1C2C11-1.3(10) Si2C17C18C27-0.2(11)
Si1C1C5Fe1120.9(5) Si2C17C21Fe2-121.2(5)
Si1C1C5C4179.7(5) Si2C17C21C20179.4(5)
C1C2C3Fe160.0(4) C17C18C19Fe2-59.9(5)
C1C2C3C40.7(7) C17C18C19C20-0.1(8)
C1C2C11N1136.4(7) C17C18C27N2-139.3(7)
C2C1C5Fe1-58.4(4) C18C17C21Fe258.3(5)
C2C1C5C40.5(7) C18C17C21C20-1.1(7)
C2C3C4Fe159.4(4) C18C19C20Fe2-59.4(5)
C2C3C4C5-0.4(7) C18C19C20C21-0.6(8)
C3C2C11N1-45.2(9) C19C18C27N240.3(9)
C3C4C5Fe159.6(4) C19C20C21Fe2-58.6(5)
C3C4C5C1-0.1(7) C19C20C21C171.1(8)
C5C1C2Fe158.0(4) C21C17C18Fe2-58.5(4)
C5C1C2C3-0.7(7) C21C17C18C190.7(8)
C5C1C2C11178.0(6) C21C17C18C27-179.6(6)
C6C7C8Fe1-62.2(6) C22C23C24Fe258.9(8)
C6C7C8C9-2.1(11) C22C23C24C250.9(12)
C7C6C10Fe158.2(6) C23C22C26Fe2-60.4(8)
C7C6C10C9-1.8(10) C23C22C26C25-2.3(11)
C7C8C9Fe1-59.2(7) C23C24C25Fe261.3(8)
C7C8C9C101.0(11) C23C24C25C26-2.1(10)
C8C9C10Fe1-59.3(6) C24C25C26Fe263.0(6)
C8C9C10C60.5(10) C24C25C26C222.6(10)
C10C6C7Fe1-58.8(6) C26C22C23Fe259.0(7)
C10C6C7C82.4(10) C26C22C23C240.9(13)
C11C2C3Fe1-118.7(6) C27C18C19Fe2120.4(7)
C11C2C3C4-178.0(6) C27C18C19C20-179.7(7)
C12N1C11C2-59.0(7) C28N2C27C1863.7(7)
C13N1C11C2176.8(5) C29N2C27C18-171.8(6)
C14Si1C1Fe174.8(5) C30Si2C17Fe2-81.0(5)
C14Si1C1C2166.9(6) C30Si2C17C18-173.9(7)
C14Si1C1C5-12.2(6) C30Si2C17C215.5(7)
C15Si1C1Fe1-45.8(5) C31Si2C17Fe2160.4(4)
C15Si1C1C246.3(7) C31Si2C17C1867.4(7)
C15Si1C1C5-132.8(6) C31Si2C17C21-113.2(6)
C16Si1C1Fe1-165.4(4) C32Si2C17Fe239.9(5)
C16Si1C1C2-73.3(7) C32Si2C17C18-53.0(8)
C16Si1C1C5107.6(6) C32Si2C17C21126.3(6)

 

Table 8 Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 3193_twin1_hklf4.
AtomxyzU(eq)
H111982332428929
H318412380283232
H414902571126834
H5-105423683030
H618657158105566
H7277161092439100
H8419144652150119
H94033442260288
H1025836072-4467
H11A13334453365932
H11B-2234481379732
H12A-7921275501453
H12B-7671821396253
H12C-15472487460553
H13A12213623518040
H13B6532252571840
H13C-3193345547240
H14A-743674250263
H14B-2203703782863
H14C-1911574967463
H15A-3096554296870
H15B-14427412259370
H15C-707477196770
H16A-32714416259361
H16B-35375708274561
H16C-27724704340361
H2-58767323438825
H19-58777380295836
H20-48047551141232
H21-2979917692331
H22-48041213599487
H23-609311512244594
H24-76579886262885
H25-733793191121138
H26-55211094811480
H27A-55569487378833
H27B-40579362390833
H28A-33287344477960
H28B-37806759408760
H28C-43276171512760
H29A-49358283559245
H29B-60337206582445
H29C-63218584528045
H30A-6651177687367
H30B-19251139654167
H30C-8571041384267
H31A-15039813350658
H31B-34110622278158
H31C-6969262280058
H32A-347611687297866
H32B-347212378194166
H32C-223812541238466

Experimental

Single crystals of C16H26ClFeNSi [3193_twin1_hklf4] were []. A suitable crystal was selected and [] on a Xcalibur, Sapphire3 diffractometer. The crystal was kept at 173.15 K during data collection. Using Olex2 [1], the structure was solved with the ShelXS [2] structure solution program using Direct Methods and refined with the ShelXL [3] refinement package using Least Squares minimisation.

  1. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.
  2. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
  3. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Crystal structure determination of [3193_twin1_hklf4]

Crystal Data for C16H26ClFeNSi (=351.77 g/mol): triclinic, space group P-1 (no. 2), a = 10.4038(9) Å, b = 11.5162(11) Å, c = 16.0747(16) Å, α = 71.308(9)°, β = 81.097(8)°, γ = 89.850(7)°, = 1800.1(3) Å3, Z = 4, T = 173.15 K, μ(MoKα) = 1.044 mm-1, Dcalc = 1.298 g/cm3, 8830 reflections measured (4.426° ≤ 2Θ ≤ 52°), 8830 unique (Rint = N/A, Rsigma = 0.1178) which were used in all calculations. The final R1 was 0.0621 (I > 2σ(I)) and wR2 was 0.1843 (all data).

Refinement model description

Number of restraints - 60, number of constraints - unknown.

Details:

1. Twinned data refinement
Scales: 0.7958(13) 0.2042(13)
2. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
At 1.5 times of:
All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C23) ≈ Ueq, Uanis(C22) ≈ Ueq, Uanis(C26) ≈ Ueq, Uanis(C25)
≈ Ueq, Uanis(C10) ≈ Ueq, Uanis(C6) ≈ Ueq, Uanis(C7) ≈ Ueq,
Uanis(C8) ≈ Ueq, Uanis(C9) ≈ Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C24) ≈ Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.0005
4.a Ternary CH refined with riding coordinates:
N1(H1), N2(H2)
4.b Secondary CH2 refined with riding coordinates:
C11(H11A,H11B), C27(H27A,H27B)
4.c Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C19(H19),
C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
4.d Idealised Me refined as rotating group:
C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
H15C), C16(H16A,H16B,H16C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,
H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)

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