- 1 - yjh0426 P n a 21 R = 0.04 : Apr 26 21:55:04 2019 =========================================== S U P P L E M E N T A R Y M A T E R I A L =========================================== B E L O N G I N G TO T H E P A P E R b y C o n t e n t s =============== Table S1 - Crystal Data and Details of the Structure Determination for: yjh0426 P n a 21 R = 0.04 Table S2 - Final Coordinates and Equivalent Isotropic Displacement Parameters of the non-Hydrogen atoms for: yjh0426 P n a 21 R = 0.04 Table S3 - Hydrogen Atom Positions and Isotropic Displacement Parameters for: yjh0426 P n a 21 R = 0.04 Table S4 - (An)isotropic Displacement Parameters for: yjh0426 P n a 21 R = 0.04 Table S5 - Bond Distances (Angstrom) for: yjh0426 P n a 21 R = 0.04 Table S6 - Bond Angles (Degrees) for: yjh0426 P n a 21 R = 0.04 Table S7 - Torsion Angles (Degrees) for: yjh0426 P n a 21 R = 0.04 Table S8 - Contact Distances(Angstrom) for: yjh0426 P n a 21 R = 0.04 Table S9 - Hydrogen Bonds (Angstrom, Deg) for: yjh0426 P n a 21 R = 0.04 - 2 - Table S1 - Crystal Data and Details of the Structure Determination for: yjh0426 P n a 21 R = 0.04 Crystal Data Formula C15 H16 Cl N5 O S4 Formula Weight 446.02 Crystal System Orthorhombic Space group Pna21 (No. 33) a, b, c [Angstrom] 9.8513(5) 7.3392(4) 26.2975(15) V [Ang**3] 1901.33(18) Z 4 D(calc) [g/cm**3] 1.558 Mu(MoKa) [ /mm ] 0.656 F(000) 920 Crystal Size [mm] 0.10 x 0.11 x 0.12 Data Collection Temperature (K) 100 Radiation [Angstrom] MoKa 0.71073 Theta Min-Max [Deg] 2.9, 28.3 Dataset -13: 10 ; -6: 9 ; -33: 31 Tot., Uniq. Data, R(int) 12108, 4343, 0.039 Observed data [I > 2.0 sigma(I)] 4013 Refinement Nref, Npar 4343, 240 R, wR2, S 0.0361, 0.0706, 1.04 w = ^2^(FO^2^)+(0.0278P)^2^+0.2206P] WHERE P=(FO^2^+2FC^2^)/3' Max. and Av. Shift/Error 0.00, 0.00 Flack x 1.00(4) Min. and Max. Resd. Dens. [e/Ang^3] -0.31, 0.28 - 3 - Table S2 - Final Coordinates and Equivalent Isotropic Displacement Parameters of the non-Hydrogen atoms for: yjh0426 P n a 21 R = 0.04 Atom x y z U(eq) [Ang^2] ---- --- --- --- ----------- Cl1 0.84821(12) 1.71842(14) -0.18605(4) 0.0326(3) S1 0.89434(8) 0.58322(12) 0.01058(4) 0.0129(2) S2 0.70018(9) -0.32372(12) 0.14592(3) 0.0158(3) S3 0.87715(9) -0.43391(14) 0.22718(4) 0.0183(3) S4 0.85263(8) 0.93470(13) -0.04699(4) 0.0187(3) O1 0.9779(2) 0.2967(3) 0.06325(10) 0.0158(8) N1 0.6343(3) 0.5635(4) 0.02239(11) 0.0123(9) N2 0.6578(3) 0.7213(4) -0.00579(11) 0.0123(9) N3 0.7494(3) 0.3199(4) 0.06014(11) 0.0103(9) N4 0.7246(3) 0.0448(4) 0.13104(10) 0.0125(9) N5 0.8222(3) -0.0846(4) 0.20866(11) 0.0137(9) C1 0.7477(3) 0.4803(5) 0.03287(13) 0.0105(10) C2 0.8658(3) 0.2350(5) 0.07398(13) 0.0119(10) C3 0.8503(3) 0.0557(5) 0.10172(14) 0.0147(11) C4 0.6356(3) -0.1055(5) 0.12024(15) 0.0151(10) C5 0.8029(3) -0.2581(5) 0.19709(13) 0.0131(10) C6 0.7438(3) 0.0673(5) 0.18508(13) 0.0150(11) C7 0.9203(4) -0.0352(6) 0.24841(14) 0.0199(11) C8 0.7860(3) 0.7480(5) -0.01442(13) 0.0123(10) C9 0.6996(3) 1.0285(5) -0.07560(16) 0.0183(11) C10 0.7392(3) 1.2007(5) -0.10330(13) 0.0136(11) C11 0.8421(4) 1.2014(6) -0.13989(15) 0.0200(11) C12 0.8783(4) 1.3601(6) -0.16453(15) 0.0213(11) C13 0.8081(4) 1.5178(6) -0.15365(14) 0.0185(11) C14 0.7038(4) 1.5211(6) -0.11834(14) 0.0193(12) C15 0.6711(3) 1.3620(5) -0.09293(13) 0.0155(11) U(eq) = 1/3 of the trace of the orthogonalized U Tensor - 4 - Table S3 - Hydrogen Atom Positions and Isotropic Displacement Parameters for: yjh0426 P n a 21 R = 0.04 Atom x y z U(iso) [Ang^2] ---- --- --- --- ----------- H3 0.674(4) 0.273(5) 0.0679(15) 0.016(10) H3A 0.85210 -0.04290 0.07720 0.0180 H3B 0.92680 0.03960 0.12450 0.0180 H4A 0.62460 -0.11650 0.08370 0.0180 H4B 0.54700 -0.08080 0.13480 0.0180 H6A 0.65560 0.07530 0.20140 0.0180 H6B 0.79110 0.18100 0.19120 0.0180 H7A 0.89670 -0.09570 0.27950 0.0300 H7B 0.91860 0.09430 0.25360 0.0300 H7C 1.00970 -0.07190 0.23810 0.0300 H9A 0.66040 0.94160 -0.09920 0.0220 H9B 0.63300 1.05550 -0.04950 0.0220 H11 0.88680 1.09330 -0.14770 0.0240 H12 0.94880 1.36070 -0.18800 0.0260 H14 0.65660 1.62830 -0.11180 0.0230 H15 0.60270 1.36310 -0.06860 0.0190 ======================================================= The Temperature Factor has the Form of Exp(-T) Where T = 8*(Pi**2)*U*(Sin(Theta)/Lambda)**2 for Isotropic Atoms - 5 - Table S4 - (An)isotropic Displacement Parameters for: yjh0426 P n a 21 R = 0.04 Atom U(1,1) or U U(2,2) U(3,3) U(2,3) U(1,3) U(1,2) ---- ------ ------ ------ ------ ------ ------ Cl1 0.0595(7) 0.0165(5) 0.0219(5) 0.0053(5) 0.0048(5) -0.0102(5) S1 0.0072(4) 0.0141(4) 0.0173(4) 0.0046(4) 0.0006(3) -0.0002(3) S2 0.0197(4) 0.0125(5) 0.0151(4) -0.0008(4) -0.0049(4) -0.0026(4) S3 0.0223(4) 0.0164(5) 0.0161(5) 0.0031(4) -0.0028(4) 0.0023(4) S4 0.0131(4) 0.0200(5) 0.0231(5) 0.0104(4) -0.0019(4) -0.0020(4) O1 0.0091(11) 0.0145(14) 0.0239(14) 0.0025(11)-0.0005(10)-0.0002(10) N1 0.0098(13) 0.0131(16) 0.0139(16) 0.0021(13) 0.0010(10) 0.0018(12) N2 0.0119(14) 0.0128(16) 0.0122(16) 0.0008(13) 0.0019(11) 0.0007(12) N3 0.0057(13) 0.0100(16) 0.0151(16) 0.0024(13) 0.0010(11)-0.0009(12) N4 0.0118(13) 0.0126(16) 0.0131(16) 0.0005(12) 0.0015(11)-0.0006(12) N5 0.0153(14) 0.0145(17) 0.0112(15) 0.0007(13)-0.0022(11)-0.0004(13) C1 0.0095(16) 0.0122(18) 0.0097(16)-0.0011(15) 0.0014(12)-0.0002(15) C2 0.0110(15) 0.0127(19) 0.0121(18)-0.0054(15) 0.0000(13) 0.0019(14) C3 0.0119(17) 0.015(2) 0.0173(19) 0.0021(16) 0.0029(12) 0.0011(15) C4 0.0135(16) 0.0172(19) 0.0145(17) 0.0027(17)-0.0012(14) 0.0020(14) C5 0.0137(16) 0.015(2) 0.0105(18) 0.0021(16) 0.0025(13)-0.0019(15) C6 0.0176(17) 0.0113(19) 0.016(2)-0.0021(16)-0.0017(14)-0.0016(15) C7 0.0198(19) 0.021(2) 0.019(2)-0.0043(17)-0.0088(15) 0.0004(17) C8 0.0126(17) 0.0130(19) 0.0112(18) 0.0006(15)-0.0011(12) 0.0012(14) C9 0.0120(16) 0.016(2) 0.027(2) 0.0057(18)-0.0012(15) 0.0008(15) C10 0.0131(16) 0.014(2) 0.0136(19) 0.0002(15)-0.0005(13) 0.0001(15) C11 0.0199(19) 0.016(2) 0.024(2) 0.0004(17) 0.0050(15) 0.0054(16) C12 0.0208(19) 0.025(2) 0.018(2) 0.0005(18) 0.0065(15)-0.0028(18) C13 0.032(2) 0.012(2) 0.0115(19) 0.0028(16)-0.0022(15)-0.0064(17) C14 0.027(2) 0.014(2) 0.017(2) 0.0001(17)-0.0010(15) 0.0059(17) C15 0.0160(18) 0.018(2) 0.0125(19)-0.0012(16) 0.0005(13) 0.0006(16) ======================================================= The Temperature Factor has the Form of Exp(-T) Where T = 8*(Pi**2)*U*(Sin(Theta)/Lambda)**2 for Isotropic Atoms T = 2*(Pi**2)*Sumij(h(i)*h(j)*U(i,j)*Astar(i)*Astar(j)), for Anisotropic Atoms. Astar(i) are Reciprocal Axial Lengths and h(i) are the Reflection Indices. - 6 - Table S5 - Bond Distances (Angstrom) for: yjh0426 P n a 21 R = 0.04 Cl1 -C13 1.746(4) C9 -C10 1.510(5) S1 -C1 1.732(3) C10 -C15 1.388(5) S1 -C8 1.742(3) C10 -C11 1.398(5) S2 -C4 1.851(4) C11 -C12 1.380(6) S2 -C5 1.751(3) C12 -C13 1.378(6) S3 -C5 1.681(4) C13 -C14 1.385(5) S4 -C8 1.744(4) C14 -C15 1.383(6) S4 -C9 1.820(3) C3 -H3A 0.9700 O1 -C2 1.227(4) C3 -H3B 0.9700 N1 -N2 1.394(4) C4 -H4A 0.9700 N1 -C1 1.303(4) C4 -H4B 0.9700 N2 -C8 1.298(4) C6 -H6A 0.9700 N3 -C1 1.379(5) C6 -H6B 0.9700 N3 -C2 1.355(4) C7 -H7A 0.9600 N4 -C3 1.461(4) C7 -H7B 0.9600 N4 -C4 1.437(5) C7 -H7C 0.9600 N4 -C6 1.443(4) C9 -H9A 0.9700 N5 -C5 1.323(5) C9 -H9B 0.9700 N5 -C6 1.491(5) C11 -H11 0.9300 N5 -C7 1.469(5) C12 -H12 0.9300 N3 -H3 0.84(4) C14 -H14 0.9300 C2 -C3 1.512(5) C15 -H15 0.9300 - 7 - Table S6 - Bond Angles (Degrees) for: yjh0426 P n a 21 R = 0.04 C1 -S1 -C8 85.38(16) S1 -C8 -S4 120.02(17) C4 -S2 -C5 103.95(17) S4 -C9 -C10 107.6(2) C8 -S4 -C9 100.86(16) C11 -C10 -C15 118.9(3) N2 -N1 -C1 111.1(3) C9 -C10 -C11 121.5(3) N1 -N2 -C8 112.3(3) C9 -C10 -C15 119.6(3) C1 -N3 -C2 122.9(3) C10 -C11 -C12 120.9(4) C3 -N4 -C4 117.1(3) C11 -C12 -C13 118.8(4) C3 -N4 -C6 113.7(3) Cl1 -C13 -C14 118.7(3) C4 -N4 -C6 111.2(3) Cl1 -C13 -C12 119.6(3) C5 -N5 -C6 123.3(3) C12 -C13 -C14 121.7(4) C5 -N5 -C7 119.7(3) C13 -C14 -C15 118.8(4) C6 -N5 -C7 116.9(3) C10 -C15 -C14 120.8(3) C1 -N3 -H3 118(3) N4 -C3 -H3A 109.00 C2 -N3 -H3 120(3) N4 -C3 -H3B 109.00 S1 -C1 -N1 116.1(3) C2 -C3 -H3A 109.00 S1 -C1 -N3 122.6(2) C2 -C3 -H3B 109.00 N1 -C1 -N3 121.4(3) H3A -C3 -H3B 108.00 O1 -C2 -N3 122.0(3) S2 -C4 -H4A 109.00 N3 -C2 -C3 116.4(3) S2 -C4 -H4B 109.00 O1 -C2 -C3 121.5(3) N4 -C4 -H4A 109.00 N4 -C3 -C2 112.8(3) N4 -C4 -H4B 109.00 S2 -C4 -N4 112.5(2) H4A -C4 -H4B 108.00 S3 -C5 -N5 124.6(3) N4 -C6 -H6A 109.00 S2 -C5 -S3 113.7(2) N4 -C6 -H6B 109.00 S2 -C5 -N5 121.6(3) N5 -C6 -H6A 109.00 N4 -C6 -N5 113.1(3) N5 -C6 -H6B 109.00 S4 -C8 -N2 124.8(3) H6A -C6 -H6B 108.00 S1 -C8 -N2 115.2(3) N5 -C7 -H7A 109.00 - 8 - Table S6 - Bond Angles (Degrees) (continued) for: yjh0426 P n a 21 R = 0.04 N5 -C7 -H7B 110.00 H9A -C9 -H9B 109.00 N5 -C7 -H7C 109.00 C10 -C11 -H11 119.00 H7A -C7 -H7B 109.00 C12 -C11 -H11 120.00 H7A -C7 -H7C 109.00 C11 -C12 -H12 121.00 H7B -C7 -H7C 109.00 C13 -C12 -H12 121.00 S4 -C9 -H9A 110.00 C13 -C14 -H14 121.00 S4 -C9 -H9B 110.00 C15 -C14 -H14 121.00 C10 -C9 -H9A 110.00 C10 -C15 -H15 120.00 C10 -C9 -H9B 110.00 C14 -C15 -H15 120.00 - 9 - Table S7 - Torsion Angles (Degrees) for: yjh0426 P n a 21 R = 0.04 C8 -S1 -C1 -N1 -0.3(3) C8 -S1 -C1 -N3 179.7(3) C1 -S1 -C8 -S4 178.6(2) C1 -S1 -C8 -N2 0.0(3) C4 -S2 -C5 -N5 -1.7(3) C5 -S2 -C4 -N4 25.8(3) C4 -S2 -C5 -S3 -179.21(18) C9 -S4 -C8 -S1 168.0(2) C8 -S4 -C9 -C10 176.8(3) C9 -S4 -C8 -N2 -13.6(4) N2 -N1 -C1 -S1 0.5(4) N2 -N1 -C1 -N3 -179.5(3) C1 -N1 -N2 -C8 -0.5(4) N1 -N2 -C8 -S4 -178.2(2) N1 -N2 -C8 -S1 0.2(4) C2 -N3 -C1 -S1 3.6(5) C2 -N3 -C1 -N1 -176.4(3) C1 -N3 -C2 -O1 0.4(5) C1 -N3 -C2 -C3 -177.3(3) C4 -N4 -C3 -C2 123.9(3) C3 -N4 -C6 -N5 -66.5(4) C3 -N4 -C4 -S2 74.1(3) C4 -N4 -C6 -N5 68.3(3) C6 -N4 -C3 -C2 -104.1(3) C6 -N4 -C4 -S2 -59.0(3) C7 -N5 -C6 -N4 141.0(3) C6 -N5 -C5 -S3 -173.2(2) C6 -N5 -C5 -S2 9.6(4) - 10 - Table S7 - Torsion Angles (Degrees) (continued) for: yjh0426 P n a 21 R = 0.04 C5 -N5 -C6 -N4 -42.1(4) C7 -N5 -C5 -S3 3.7(5) C7 -N5 -C5 -S2 -173.6(2) N3 -C2 -C3 -N4 -28.9(4) O1 -C2 -C3 -N4 153.3(3) S4 -C9 -C10 -C15 -126.5(3) S4 -C9 -C10 -C11 54.5(4) C15 -C10 -C11 -C12 1.6(5) C9 -C10 -C15 -C14 -178.9(3) C9 -C10 -C11 -C12 -179.3(3) C11 -C10 -C15 -C14 0.2(5) C10 -C11 -C12 -C13 -2.1(6) C11 -C12 -C13 -C14 0.8(6) C11 -C12 -C13 -Cl1 -177.7(3) Cl1 -C13 -C14 -C15 179.5(3) C12 -C13 -C14 -C15 1.0(6) C13 -C14 -C15 -C10 -1.4(5) - 11 - Table S8 - Contact Distances(Angstrom) for: yjh0426 P n a 21 R = 0.04 Cl1 .H11_a 2.9500 O1 .N3_e 2.809(4) Cl1 .H7B_b 3.1100 O1 .N4_e 3.231(4) Cl1 .H6A_c 3.1400 O1 .C4_e 3.130(4) S1 .O1 2.649(2) O1 .H3_e 2.00(4) S1 .N2 2.577(3) O1 .H4A_e 2.8100 S1 .N1_d 3.522(3) O1 .H4B_e 2.8900 S1 .N2_d 2.997(3) N1 .S1 2.585(3) S2 .N3_f 3.488(3) N1 .S2_a 3.415(3) S2 .C1_f 3.336(4) N1 .C15_f 3.393(5) S2 .N1_f 3.415(3) N1 .S4_k 3.321(3) S4 .N1_d 3.321(3) N1 .O1_l 3.243(4) S4 .N2_d 3.395(3) N1 .S1_k 3.522(3) S4 .C15_j 3.678(3) N2 .C14_f 3.335(5) S1 .H4A_e 2.9800 N2 .S1 2.577(3) S1 .H9B_d 3.0100 N2 .S4_k 3.395(3) S2 .H3A 3.1200 N2 .S1_k 2.997(3) S2 .H3B_g 3.1800 N3 .N4 2.759(4) S2 .H7C_g 3.1600 N3 .S2_a 3.488(3) S3 .H12_h 2.8600 N3 .O1_l 2.809(4) S3 .H4B_i 2.9500 N4 .N3 2.759(4) S3 .H6A_i 3.0100 N4 .O1_l 3.231(4) S3 .H7C 2.9700 N1 .H4A_a 2.8500 S3 .H6B_f 3.1000 N1 .H15_f 2.8300 S3 .H7A 2.8400 N2 .H14_f 2.8700 S4 .H11 2.9100 N2 .H4A_a 2.6600 S4 .H15_j 2.9300 N2 .H9B 2.7200 O1 .S1 2.649(2) N2 .H9A 2.9400 O1 .N1_e 3.243(4) N4 .H3 2.41(4) - 12 - Table S8 - Contact Distances(Angstrom) (continued) for: yjh0426 P n a 21 R = 0.04 N5 .H3B 2.6100 H3B .H6B 2.4400 C1 .S2_a 3.336(4) H3B .S2_i 3.1800 C1 .C15_f 3.503(5) H4A .N1_f 2.8500 C3 .C5 3.437(5) H4A .N2_f 2.6600 C4 .O1_l 3.130(4) H4A .H3A 2.3100 C5 .C3 3.437(5) H4A .S1_l 2.9800 C7 .C13_m 3.442(5) H4A .O1_l 2.8100 C8 .C14_f 3.301(5) H4B .H6A 2.3500 C11 .C15_j 3.500(5) H4B .S3_g 2.9500 C13 .C7_c 3.442(5) H4B .O1_l 2.8900 C14 .C8_a 3.301(5) H6A .H4B 2.3500 C14 .N2_a 3.335(5) H6A .Cl1_m 3.1400 C15 .N1_a 3.393(5) H6A .S3_g 3.0100 C15 .C1_a 3.503(5) H6B .S3_a 3.1000 C15 .C11_n 3.500(5) H6B .H3B 2.4400 C15 .S4_n 3.678(3) H6B .H7B 2.1600 C2 .H3_e 3.04(4) H7A .S3 2.8400 C8 .H14_f 2.9900 H7A .C13_m 2.8000 C8 .H3A_a 2.9300 H7A .C14_m 2.9900 C13 .H7A_c 2.8000 H7B .H6B 2.1600 C14 .H7A_c 2.9900 H7B .Cl1_o 3.1100 H3 .N4 2.41(4) H7C .S3 2.9700 H3 .O1_l 2.00(4) H7C .S2_i 3.1600 H3 .C2_l 3.04(4) H9A .N2 2.9400 H3A .S2 3.1200 H9A .H14_f 2.3200 H3A .C8_f 2.9300 H9B .N2 2.7200 H3A .H4A 2.3100 H9B .H15 2.3300 H3B .N5 2.6100 H9B .S1_k 3.0100 - 13 - Table S8 - Contact Distances(Angstrom) (continued) for: yjh0426 P n a 21 R = 0.04 H11 .Cl1_f 2.9500 H14 .H9A_a 2.3200 H11 .S4 2.9100 H15 .N1_a 2.8300 H12 .S3_p 2.8600 H15 .H9B 2.3300 H14 .N2_a 2.8700 H15 .S4_n 2.9300 H14 .C8_a 2.9900 - 14 - Table S9 - Hydrogen Bonds (Angstrom, Deg) for: yjh0426 P n a 21 R = 0.04 N3 -- H3 .. N4 0.84(4) 2.41(4) 2.759(4) 106(3) . N3 -- H3 .. O1 0.84(4) 2.00(4) 2.809(4) 160(4) 4_455 C3 -- H3B .. N5 0.9700 2.6100 3.008(5) 105.00 . C12 -- H12 .. S3 0.9300 2.8600 3.769(4) 165.00 2_764 - 15 - Translation of Symmetry Code to Equiv.Pos a =[ 1565.00 ] = x,1+y,z b =[ 2774.00 ] = 2-x,2-y,-1/2+z c =[ 3664.00 ] = 3/2-x,3/2+y,-1/2+z d =[ 4565.00 ] = 1/2+x,3/2-y,z e =[ 4555.00 ] = 1/2+x,1/2-y,z f =[ 1545.00 ] = x,-1+y,z g =[ 4445.00 ] = -1/2+x,-1/2-y,z h =[ 2765.00 ] = 2-x,1-y,1/2+z i =[ 4545.00 ] = 1/2+x,-1/2-y,z j =[ 4575.00 ] = 1/2+x,5/2-y,z k =[ 4465.00 ] = -1/2+x,3/2-y,z l =[ 4455.00 ] = -1/2+x,1/2-y,z m =[ 3635.00 ] = 3/2-x,-3/2+y,1/2+z n =[ 4475.00 ] = -1/2+x,5/2-y,z o =[ 2775.00 ] = 2-x,2-y,1/2+z p =[ 2764.00 ] = 2-x,1-y,-1/2+z