4

Table 1 Crystal data and structure refinement for 4.
Identification code 4
Empirical formula C11H6.5ClN3O3S
Formula weight 296.20
Temperature/K 295.3(9)
Crystal system triclinic
Space group P-1
a/Å 4.9572(2)
b/Å 16.7370(5)
c/Å 17.3370(7)
α/° 109.745(3)
β/° 90.661(3)
γ/° 94.347(3)
Volume/Å3 1348.90(9)
Z 4
ρcalcg/cm3 1.459
μ/mm‑1 4.043
F(000) 602.0
Crystal size/mm3 0.3 × 0.05 × 0.04
Radiation CuKα (λ = 1.54184)
2Θ range for data collection/° 17.96 to 152.482
Index ranges -6 ≤ h ≤ 6, -20 ≤ k ≤ 16, -19 ≤ l ≤ 21
Reflections collected 6909
Independent reflections 4344 [Rint = 0.2129, Rsigma = 0.1163]
Data/restraints/parameters 4344/0/401
Goodness-of-fit on F2 1.000
Final R indexes [I>=2σ (I)] R1 = 0.0941, wR2 = 0.2386
Final R indexes [all data] R1 = 0.1474, wR2 = 0.2575
Largest diff. peak/hole / e Å-3 0.89/-0.55

 

Table 2 Fractional Atomic Coordinates (×104) and Equivalent Isotropic Displacement Parameters (Å2×103) for 4. Ueq is defined as 1/3 of of the trace of the orthogonalised UIJ tensor.
AtomxyzU(eq)
Cl1A9460(3)5656.5(12)9342.3(9)78.9(5)
O1A1283(7)6279(2)7193(2)55.4(8)
O2A-1866(7)5849(2)6204(2)58.9(8)
C2A-70(9)5648(3)6556(3)46.6(9)
C9A3278(9)6127(3)7673(3)49.2(9)
C8A4490(12)6803(3)8310(4)64.3(13)
C7A6431(12)6672(4)8815(4)65.7(13)
C6A7122(10)5837(4)8677(3)56.2(11)
C5A5977(10)5165(3)8044(3)52.6(10)
C10A3984(8)5292(3)7516(3)44.6(9)
C4A2699(9)4628(3)6838(3)45.7(9)
S11A-3369(2)4172.2(7)5116.0(7)48.5(3)
N14A461(8)3352(2)5388(2)49.8(8)
N13A-1066(7)2777(2)4745(3)48.7(8)
N16A-4962(8)2667(3)3931(3)58.4(10)
C3A794(8)4783(3)6358(3)42.2(8)
C15A-491(8)4105(3)5655(2)41.7(8)
C12A-3149(8)3114(3)4548(3)45.8(9)
Cl1B16572(4)1198.5(18)9531.6(13)107.5(7)
O1B10927(8)3152(2)7897(3)66.3(9)
O2B7739(9)3300(2)7077(3)72.1(10)
C2B8812(11)2811(3)7328(3)56.5(11)
C9B12242(11)2671(4)8247(3)61.2(12)
C8B14326(12)3078(4)8826(4)73.0(16)
C7B15649(13)2616(5)9209(4)81.8(19)
C6B14931(12)1749(5)9016(4)71.0(15)
C5B12903(11)1336(4)8439(3)62.6(12)
C10B11530(10)1797(3)8048(3)53.7(10)
C4B9420(9)1424(3)7428(3)50.8(10)
C3B8093(9)1895(3)7085(3)47.9(9)
S11B4290(2)2116.6(7)5952.8(8)54.3(3)
N14B4897(8)745(2)6258(2)51.0(8)
N13B2850(8)535(2)5679(3)52.6(9)
N16B386(10)1129(3)4878(3)63.5(11)
C15B5886(9)1542(3)6468(3)45.9(9)
C12B2293(10)1180(3)5444(3)52.6(10)
O2-178(12)-756(4)7475(4)51.4(14)
O14865(10)-736(3)6752(3)78.8(12)
O3-440(30)-1408(10)7837(10)67(4)
O4-400(60)-1083(16)8707(15)118(9)

 

Table 3 Anisotropic Displacement Parameters (Å2×103) for 4. The Anisotropic displacement factor exponent takes the form: -2π2[h2a*2U11+2hka*b*U12+…].
AtomU11U22U33U23U13U12
Cl1A77.4(9)79.6(11)70.9(8)16.6(7)-21.7(6)-1.8(7)
O1A65(2)31.7(16)68.3(19)15.0(14)0.6(14)5.5(13)
O2A60(2)44.8(19)79(2)27.6(16)1.6(15)16.6(15)
C2A46(2)35(2)60(2)17.0(18)8.9(16)4.9(17)
C9A56(3)33(2)58(2)14.9(18)5.2(17)-0.3(17)
C8A77(4)34(3)73(3)8(2)3(2)-4(2)
C7A75(3)45(3)64(3)5(2)-1(2)-10(2)
C6A55(3)52(3)56(2)14(2)-1.6(17)-6(2)
C5A54(2)44(2)58(2)14.6(19)-1.7(17)0.3(19)
C10A45(2)33(2)53(2)11.7(16)1.8(15)-2.2(16)
C4A47(2)31(2)57(2)12.5(17)2.3(15)-1.4(16)
S11A42.8(6)38.0(6)64.4(6)15.8(4)-2.9(4)9.5(4)
N14A48.5(19)32.2(18)67(2)15.0(16)-9.4(14)3.7(14)
N13A41.9(18)33.8(18)69(2)15.8(16)-5.0(14)1.0(14)
N16A44(2)47(2)78(3)13.7(19)-12.2(16)4.1(16)
C3A44(2)27(2)56(2)16.0(16)4.8(15)0.5(15)
C15A40.0(19)33(2)55(2)18.6(17)1.1(14)3.7(15)
C12A35.9(19)41(2)65(2)23.2(19)2.3(15)3.0(16)
Cl1B94.3(13)135(2)97.1(12)45.1(12)-25.3(9)10.6(12)
O1B75(2)36.0(18)78(2)8.4(16)6.9(17)-9.3(16)
O2B84(3)37(2)98(3)25.8(19)8(2)5.1(17)
C2B60(3)36(2)72(3)17(2)14(2)0.2(19)
C9B60(3)47(3)62(3)2(2)9(2)-9(2)
C8B68(3)62(4)70(3)2(3)3(2)-17(3)
C7B69(4)89(5)64(3)0(3)2(2)-16(3)
C6B64(3)84(4)62(3)21(3)3(2)1(3)
C5B56(3)61(3)65(3)16(2)0(2)-3(2)
C10B50(2)46(3)60(2)13(2)8.6(17)-2.7(19)
C4B47(2)34(2)68(3)13.1(19)3.6(17)-4.2(17)
C3B47(2)32(2)61(2)13.2(18)12.9(17)-2.1(17)
S11B55.5(7)37.1(6)77.8(7)28.8(5)6.3(5)5.0(4)
N14B59(2)34.2(19)61(2)16.5(16)0.2(15)4.6(16)
N13B59(2)31.5(19)68(2)17.9(16)-2.6(16)3.9(15)
N16B68(3)41(2)86(3)28(2)-15(2)3(2)
C15B49(2)31(2)61(2)19.6(17)9.0(16)5.5(16)
C12B52(2)42(2)68(3)24(2)10.7(18)11.8(19)
O242(3)50(4)75(4)40(3)-8(2)-8(2)
O180(3)58(3)110(3)43(2)-1(2)9(2)
O390(10)45(8)82(9)47(7)-25(7)-13(7)
O4210(30)76(15)88(14)55(12)-32(14)-2(14)

 

Table 4 Bond Lengths for 4.
AtomAtomLength/Å AtomAtomLength/Å
Cl1AC6A1.739(5) Cl1BC6B1.722(7)
O1AC2A1.368(6) O1BC2B1.380(7)
O1AC9A1.377(6) O1BC9B1.357(8)
O2AC2A1.204(6) O2BC2B1.202(7)
C2AC3A1.469(6) C2BC3B1.460(6)
C9AC8A1.378(7) C9BC8B1.395(8)
C9AC10A1.403(6) C9BC10B1.401(7)
C8AC7A1.372(9) C8BC7B1.372(11)
C7AC6A1.405(8) C7BC6B1.391(11)
C6AC5A1.358(7) C6BC5B1.376(8)
C5AC10A1.415(6) C5BC10B1.392(8)
C10AC4A1.420(6) C10BC4B1.436(7)
C4AC3A1.348(6) C4BC3B1.339(7)
S11AC15A1.728(4) C3BC15B1.462(6)
S11AC12A1.723(5) S11BC15B1.740(4)
N14AN13A1.374(5) S11BC12B1.740(6)
N14AC15A1.314(5) N14BN13B1.359(6)
N13AC12A1.308(5) N14BC15B1.312(6)
N16AC12A1.360(6) N13BC12B1.322(6)
C3AC15A1.455(6) N16BC12B1.332(7)

 

Table 5 Bond Angles for 4.
AtomAtomAtomAngle/˚ AtomAtomAtomAngle/˚
C2AO1AC9A123.0(3) C9BO1BC2B122.1(4)
O1AC2AC3A117.3(4) O1BC2BC3B117.4(5)
O2AC2AO1A117.2(4) O2BC2BO1B116.5(5)
O2AC2AC3A125.5(4) O2BC2BC3B126.1(5)
O1AC9AC8A118.7(4) O1BC9BC8B117.8(5)
O1AC9AC10A119.7(4) O1BC9BC10B121.7(5)
C8AC9AC10A121.7(5) C8BC9BC10B120.5(6)
C7AC8AC9A120.3(5) C7BC8BC9B119.3(6)
C8AC7AC6A118.7(5) C8BC7BC6B120.2(6)
C7AC6ACl1A119.2(4) C7BC6BCl1B118.8(5)
C5AC6ACl1A119.1(4) C5BC6BCl1B120.1(6)
C5AC6AC7A121.7(5) C5BC6BC7B121.1(6)
C6AC5AC10A120.1(5) C6BC5BC10B119.4(6)
C9AC10AC5A117.5(4) C9BC10BC4B116.8(5)
C9AC10AC4A118.7(4) C5BC10BC9B119.5(5)
C5AC10AC4A123.8(4) C5BC10BC4B123.7(5)
C3AC4AC10A121.4(4) C3BC4BC10B121.8(5)
C12AS11AC15A86.8(2) C2BC3BC15B116.6(4)
C15AN14AN13A113.2(3) C4BC3BC2B120.0(5)
C12AN13AN14A111.6(4) C4BC3BC15B123.4(4)
C4AC3AC2A119.8(4) C12BS11BC15B86.9(2)
C4AC3AC15A121.4(4) C15BN14BN13B113.5(4)
C15AC3AC2A118.8(4) C12BN13BN14B112.8(4)
N14AC15AS11A113.5(3) C3BC15BS11B124.6(3)
N14AC15AC3A120.8(4) N14BC15BC3B121.9(4)
C3AC15AS11A125.6(3) N14BC15BS11B113.4(3)
N13AC12AS11A114.8(4) N13BC12BS11B113.4(4)
N13AC12AN16A122.3(4) N13BC12BN16B123.9(5)
N16AC12AS11A122.8(3) N16BC12BS11B122.7(4)

 

Table 6 Torsion Angles for 4.
ABCDAngle/˚ ABCDAngle/˚
Cl1AC6AC5AC10A177.2(4) Cl1BC6BC5BC10B177.7(4)
O1AC2AC3AC4A5.2(6) O1BC2BC3BC4B1.8(6)
O1AC2AC3AC15A-176.5(4) O1BC2BC3BC15B-178.7(4)
O1AC9AC8AC7A178.1(5) O1BC9BC8BC7B178.2(5)
O1AC9AC10AC5A-177.8(4) O1BC9BC10BC5B-178.5(4)
O1AC9AC10AC4A3.0(6) O1BC9BC10BC4B2.8(7)
O2AC2AC3AC4A-175.0(5) O2BC2BC3BC4B-178.5(5)
O2AC2AC3AC15A3.4(7) O2BC2BC3BC15B1.0(7)
C2AO1AC9AC8A-178.9(4) C2BO1BC9BC8B-179.0(5)
C2AO1AC9AC10A-0.3(6) C2BO1BC9BC10B0.2(7)
C2AC3AC15AS11A-11.6(6) C2BC3BC15BS11B5.6(5)
C2AC3AC15AN14A170.7(4) C2BC3BC15BN14B-173.5(4)
C9AO1AC2AO2A176.5(4) C9BO1BC2BO2B177.8(5)
C9AO1AC2AC3A-3.7(6) C9BO1BC2BC3B-2.5(7)
C9AC8AC7AC6A-0.8(9) C9BC8BC7BC6B0.4(9)
C9AC10AC4AC3A-1.4(6) C9BC10BC4BC3B-3.4(7)
C8AC9AC10AC5A0.6(7) C8BC9BC10BC5B0.6(7)
C8AC9AC10AC4A-178.6(4) C8BC9BC10BC4B-178.1(5)
C8AC7AC6ACl1A-177.0(4) C8BC7BC6BCl1B-178.1(5)
C8AC7AC6AC5A1.9(9) C8BC7BC6BC5B0.4(9)
C7AC6AC5AC10A-1.6(8) C7BC6BC5BC10B-0.7(8)
C6AC5AC10AC9A0.4(7) C6BC5BC10BC9B0.2(8)
C6AC5AC10AC4A179.5(4) C6BC5BC10BC4B178.9(5)
C5AC10AC4AC3A179.5(4) C5BC10BC4BC3B177.9(5)
C10AC9AC8AC7A-0.4(8) C10BC9BC8BC7B-0.9(8)
C10AC4AC3AC2A-2.7(6) C10BC4BC3BC2B1.2(7)
C10AC4AC3AC15A179.0(4) C10BC4BC3BC15B-178.3(4)
C4AC3AC15AS11A166.8(3) C4BC3BC15BS11B-174.9(4)
C4AC3AC15AN14A-11.0(6) C4BC3BC15BN14B6.0(6)
N14AN13AC12AS11A1.7(5) N14BN13BC12BS11B-1.0(5)
N14AN13AC12AN16A-179.7(4) N14BN13BC12BN16B179.4(5)
N13AN14AC15AS11A-0.9(5) N13BN14BC15BC3B179.7(4)
N13AN14AC15AC3A177.2(4) N13BN14BC15BS11B0.5(5)
C15AS11AC12AN13A-1.8(4) C15BS11BC12BN13B1.0(4)
C15AS11AC12AN16A179.6(4) C15BS11BC12BN16B-179.3(5)
C15AN14AN13AC12A-0.5(6) C15BN14BN13BC12B0.3(6)
C12AS11AC15AN14A1.4(4) C12BS11BC15BC3B179.9(4)
C12AS11AC15AC3A-176.5(4) C12BS11BC15BN14B-0.8(3)

 

Table 7 Hydrogen Atom Coordinates (Å×104) and Isotropic Displacement Parameters (Å2×103) for 4.
AtomxyzU(eq)
H8A3860(150)7430(60)8500(50)90(20)
H7A7140(170)7090(70)9440(60)120(30)
H4A3330(110)3900(40)6620(40)59(15)
H16C-5361.822170.313964.170
H16D-6408.672930.713974.8270
H8B14590(130)3790(50)8850(40)73(18)
H7B18100(170)2650(70)9530(60)120(30)
H5B12880(170)680(70)8320(60)110(30)
H4B8850(100)870(40)7310(30)46(12)
H1A5607.69-277.066712.81118
H1B3211.46-739.876613.76118
H16A-580(120)690(40)4730(40)53(15)
H16B160(120)1660(40)4780(40)61(15)

 

Table 8 Atomic Occupancy for 4.
AtomOccupancy AtomOccupancy AtomOccupancy
O20.5 O30.25 O40.25
4

4

Table 1 Crystal data and structure refinement for 4.
Identification code 4
Empirical formula C11H6.5ClN3O3S
Formula weight 296.20
Temperature/K 295.3(9)
Crystal system triclinic
Space group P-1
a/Å 4.9572(2)
b/Å 16.7370(5)
c/Å 17.3370(7)
α/° 109.745(3)
β/° 90.661(3)
γ/° 94.347(3)
Volume/Å3 1348.90(9)
Z 4
ρcalcg/cm3 1.459
μ/mm‑1 4.043
F(000) 602.0
Crystal size/mm3 0.3 × 0.05 × 0.04
Radiation CuKα (λ = 1.54184)
2Θ range for data collection/° 17.96 to 152.482
Index ranges -6 ≤ h ≤ 6, -20 ≤ k ≤ 16, -19 ≤ l ≤ 21
Reflections collected 6909
Independent reflections 4344 [Rint = 0.2129, Rsigma = 0.1163]
Data/restraints/parameters 4344/0/401
Goodness-of-fit on F2 1.000
Final R indexes [I>=2σ (I)] R1 = 0.0941, wR2 = 0.2386
Final R indexes [all data] R1 = 0.1474, wR2 = 0.2575
Largest diff. peak/hole / e Å-3 0.89/-0.55