Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016017/si2010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016017/si2010Isup2.hkl |
CCDC reference: 647330
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C18H20N2S3 | F(000) = 760 |
Mr = 360.54 | Dx = 1.328 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 15496 reflections |
a = 15.4391 (6) Å | θ = 3.6–31.9° |
b = 5.9873 (2) Å | µ = 0.41 mm−1 |
c = 19.5007 (7) Å | T = 110 K |
V = 1802.62 (11) Å3 | Rectangular block, colourless |
Z = 4 | 0.6 × 0.5 × 0.2 mm |
Oxford Xcalibur2 CCD area-detector diffractometer | 5600 reflections with I > 2σ(I) |
ω scans | Rint = 0.011 |
Absorption correction: multi-scan [CrysAlis RED (Oxford Diffraction, 2006; Blessing, 1995)] | θmax = 32.0°, θmin = 3.7° |
Tmin = 0.790, Tmax = 0.92 | h = −21→23 |
17289 measured reflections | k = −7→8 |
5679 independent reflections | l = −27→29 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.051P)2 + 0.5189P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.029 | (Δ/σ)max = 0.001 |
wR(F2) = 0.082 | Δρmax = 0.46 e Å−3 |
S = 1.12 | Δρmin = −0.37 e Å−3 |
5679 reflections | Absolute structure: Flack (1983), 2483 Friedel pairs |
209 parameters | Absolute structure parameter: 0.41 (4) |
95 restraints |
Experimental. IR (KBr, ν, cm-1): 473 (m), 698 (str), 831 (str), 977 (m), 1095 (str), 1198 (str), 1220 (str), 1323 (str), 1365 (str), 1445 (m) 1545 (s), 2713 (str), 2805 (str), 2943 (str), 3084 (m) (w = weak, str = strong, m = moderate). 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 7.36 (d, 1H), 7.20 (d, 2H), 7.16 (S, 1H), 6.96 (t, 1H), 6.92 (t, 2H), 6.86 (s, 2H), 4.35 (s, 1H), 3.95 (d, 2H), 3.60 (d, 2H), 3.12 (m, 2H), 2.38 (s, 2H), 1.70 (m, 2H). 13C NMR (125 MHz, CDCl3, δ, p.p.m.): 22.9, 30,8, 49.0, 52.8, 76.7, 76.9, 77.2, 79.25, 124.7, 125.4, 125.65, 126.3, 126.4, 127.6, 142.8, 145.1, 185, 208. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.00001 (11) | 0.9888 (3) | −0.89257 (8) | 0.0209 (3) | |
H1 | 0.0091 | 1.1214 | −0.9183 | 0.025* | |
C2 | −0.06152 (11) | 0.8331 (3) | −0.90790 (8) | 0.0241 (3) | |
H2 | −0.0998 | 0.8472 | −0.9458 | 0.029* | |
C3 | −0.06329 (9) | 0.6446 (2) | −0.86143 (7) | 0.0180 (2) | |
H3 | −0.1017 | 0.521 | −0.8644 | 0.022* | |
C4 | 0.00179 (8) | 0.6741 (2) | −0.81054 (6) | 0.0136 (2) | |
C5 | 0.02754 (8) | 0.5155 (2) | −0.75444 (7) | 0.0137 (2) | |
H5A | −0.0224 | 0.4196 | −0.7423 | 0.016* | |
H5B | 0.075 | 0.4178 | −0.7708 | 0.016* | |
C6 | 0.11383 (8) | 0.5050 (2) | −0.64952 (6) | 0.0109 (2) | |
H6 | 0.0808 | 0.3757 | −0.6302 | 0.013* | |
C7 | 0.18942 (8) | 0.4201 (2) | −0.69011 (6) | 0.0108 (2) | |
C8 | 0.21565 (8) | 0.2040 (2) | −0.69975 (7) | 0.0132 (2) | |
H8 | 0.1864 | 0.0783 | −0.6811 | 0.016* | |
C9 | 0.29187 (8) | 0.1886 (2) | −0.74101 (8) | 0.0163 (2) | |
H9 | 0.319 | 0.0513 | −0.7527 | 0.02* | |
C10 | 0.32141 (9) | 0.3920 (2) | −0.76182 (8) | 0.0183 (3) | |
H10 | 0.3714 | 0.4137 | −0.7894 | 0.022* | |
C11 | 0.20893 (10) | 0.5386 (2) | −0.54955 (7) | 0.0183 (3) | |
H11A | 0.2525 | 0.4643 | −0.579 | 0.022* | |
H11B | 0.1804 | 0.4225 | −0.5213 | 0.022* | |
C12 | 0.25324 (9) | 0.7043 (3) | −0.50349 (7) | 0.0181 (3) | |
C13 | 0.26842 (10) | 0.6887 (3) | −0.43220 (7) | 0.0213 (3) | |
H13 | 0.2493 | 0.5692 | −0.404 | 0.026* | |
C14 | 0.31620 (12) | 0.8766 (4) | −0.40854 (10) | 0.0351 (4) | |
H14 | 0.3353 | 0.8928 | −0.3625 | 0.042* | |
C15 | 0.33176 (12) | 1.0293 (3) | −0.45774 (12) | 0.0348 (4) | |
H15 | 0.3619 | 1.1653 | −0.4501 | 0.042* | |
C16 | 0.07041 (9) | 0.7217 (3) | −0.55082 (7) | 0.0188 (3) | |
H16A | 0.0914 | 0.8145 | −0.5122 | 0.023* | |
H16B | 0.0407 | 0.5894 | −0.5315 | 0.023* | |
C17 | 0.00734 (9) | 0.8557 (3) | −0.59415 (8) | 0.0191 (3) | |
H17A | −0.0441 | 0.8959 | −0.5664 | 0.023* | |
H17B | 0.0353 | 0.9954 | −0.6099 | 0.023* | |
C18 | −0.02019 (8) | 0.7176 (3) | −0.65545 (7) | 0.0169 (2) | |
H18A | −0.0547 | 0.588 | −0.6398 | 0.02* | |
H18B | −0.057 | 0.8092 | −0.6861 | 0.02* | |
N2 | 0.14392 (7) | 0.64972 (19) | −0.59294 (6) | 0.01318 (19) | |
N1 | 0.05635 (7) | 0.63855 (19) | −0.69341 (6) | 0.01153 (18) | |
S1 | 0.05886 (2) | 0.91768 (6) | −0.82157 (2) | 0.02021 (8) | |
S2 | 0.25692 (2) | 0.60454 (5) | −0.73185 (2) | 0.01583 (7) | |
S3 | 0.29124 (3) | 0.95067 (7) | −0.53518 (2) | 0.02872 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0262 (7) | 0.0187 (6) | 0.0177 (6) | 0.0009 (5) | −0.0023 (5) | 0.0028 (5) |
C2 | 0.0275 (7) | 0.0259 (7) | 0.0190 (7) | −0.0010 (6) | −0.0084 (5) | 0.0002 (6) |
C3 | 0.0211 (6) | 0.0180 (6) | 0.0149 (6) | 0.0028 (5) | 0.0005 (5) | 0.0063 (5) |
C4 | 0.0126 (5) | 0.0140 (5) | 0.0143 (6) | −0.0002 (4) | −0.0005 (4) | −0.0013 (4) |
C5 | 0.0138 (5) | 0.0148 (5) | 0.0126 (5) | 0.0002 (4) | −0.0027 (4) | −0.0016 (4) |
C6 | 0.0118 (5) | 0.0096 (5) | 0.0113 (5) | 0.0004 (4) | −0.0005 (4) | −0.0012 (4) |
C7 | 0.0105 (5) | 0.0089 (5) | 0.0130 (5) | −0.0010 (4) | 0.0005 (4) | −0.0010 (4) |
C8 | 0.0136 (5) | 0.0093 (5) | 0.0166 (6) | 0.0002 (4) | 0.0011 (4) | −0.0002 (4) |
C9 | 0.0144 (5) | 0.0117 (5) | 0.0228 (6) | 0.0018 (4) | 0.0030 (4) | −0.0022 (5) |
C10 | 0.0131 (5) | 0.0151 (6) | 0.0266 (7) | 0.0004 (5) | 0.0059 (5) | −0.0016 (5) |
C11 | 0.0234 (6) | 0.0178 (6) | 0.0136 (6) | 0.0040 (5) | −0.0067 (4) | −0.0025 (5) |
C12 | 0.0175 (6) | 0.0223 (7) | 0.0144 (5) | 0.0024 (5) | −0.0026 (4) | −0.0035 (5) |
C13 | 0.0207 (6) | 0.0281 (7) | 0.0152 (6) | −0.0056 (6) | −0.0131 (5) | 0.0063 (5) |
C14 | 0.0243 (8) | 0.0566 (12) | 0.0244 (8) | 0.0000 (8) | −0.0085 (6) | −0.0168 (8) |
C15 | 0.0244 (8) | 0.0316 (9) | 0.0484 (11) | −0.0017 (7) | −0.0073 (7) | −0.0185 (8) |
C16 | 0.0196 (6) | 0.0224 (6) | 0.0143 (6) | 0.0034 (5) | 0.0017 (4) | −0.0056 (5) |
C17 | 0.0163 (6) | 0.0198 (6) | 0.0211 (6) | 0.0044 (5) | 0.0035 (5) | −0.0071 (5) |
C18 | 0.0114 (5) | 0.0228 (6) | 0.0165 (6) | 0.0036 (5) | 0.0017 (4) | −0.0042 (5) |
N2 | 0.0143 (4) | 0.0138 (4) | 0.0115 (5) | 0.0031 (4) | −0.0023 (4) | −0.0042 (4) |
N1 | 0.0102 (4) | 0.0128 (4) | 0.0115 (4) | 0.0027 (3) | −0.0002 (3) | −0.0021 (4) |
S1 | 0.02086 (16) | 0.01746 (15) | 0.02231 (16) | −0.00116 (12) | −0.00351 (12) | 0.00044 (13) |
S2 | 0.01320 (13) | 0.00905 (12) | 0.02523 (16) | −0.00133 (10) | 0.00474 (12) | −0.00002 (12) |
S3 | 0.0379 (2) | 0.02175 (17) | 0.02652 (19) | −0.00189 (16) | −0.00085 (16) | −0.00150 (15) |
C1—C2 | 1.364 (2) | C10—H10 | 0.95 |
C1—S1 | 1.7102 (16) | C11—N2 | 1.4719 (17) |
C1—H1 | 0.95 | C11—C12 | 1.503 (2) |
C2—C3 | 1.448 (2) | C11—H11A | 0.99 |
C2—H2 | 0.95 | C11—H11B | 0.99 |
C3—C4 | 1.4233 (19) | C12—C13 | 1.4128 (19) |
C3—H3 | 0.95 | C12—S3 | 1.7035 (16) |
C4—C5 | 1.5021 (19) | C13—C14 | 1.422 (3) |
C4—S1 | 1.7176 (14) | C13—H13 | 0.95 |
C5—N1 | 1.4687 (16) | C14—C15 | 1.347 (3) |
C5—H5A | 0.99 | C14—H14 | 0.95 |
C5—H5B | 0.99 | C15—S3 | 1.701 (2) |
C6—N1 | 1.4696 (16) | C15—H15 | 0.95 |
C6—N2 | 1.4779 (16) | C16—N2 | 1.4658 (17) |
C6—C7 | 1.4989 (17) | C16—C17 | 1.518 (2) |
C6—H6 | 1 | C16—H16A | 0.99 |
C7—C8 | 1.3687 (17) | C16—H16B | 0.99 |
C7—S2 | 1.7228 (13) | C17—C18 | 1.514 (2) |
C8—C9 | 1.4287 (18) | C17—H17A | 0.99 |
C8—H8 | 0.95 | C17—H17B | 0.99 |
C9—C10 | 1.3625 (19) | C18—N1 | 1.4726 (16) |
C9—H9 | 0.95 | C18—H18A | 0.99 |
C10—S2 | 1.7181 (14) | C18—H18B | 0.99 |
C2—C1—S1 | 112.17 (12) | H11A—C11—H11B | 108.1 |
C2—C1—H1 | 123.9 | C13—C12—C11 | 128.30 (14) |
S1—C1—H1 | 123.9 | C13—C12—S3 | 110.92 (11) |
C1—C2—C3 | 114.14 (14) | C11—C12—S3 | 120.77 (11) |
C1—C2—H2 | 122.9 | C12—C13—C14 | 110.67 (15) |
C3—C2—H2 | 122.9 | C12—C13—H13 | 124.7 |
C4—C3—C2 | 109.05 (13) | C14—C13—H13 | 124.7 |
C4—C3—H3 | 125.5 | C15—C14—C13 | 113.48 (15) |
C2—C3—H3 | 125.5 | C15—C14—H14 | 123.3 |
C3—C4—C5 | 128.05 (12) | C13—C14—H14 | 123.3 |
C3—C4—S1 | 112.34 (10) | C14—C15—S3 | 112.27 (14) |
C5—C4—S1 | 119.49 (9) | C14—C15—H15 | 123.9 |
N1—C5—C4 | 110.68 (11) | S3—C15—H15 | 123.9 |
N1—C5—H5A | 109.5 | N2—C16—C17 | 109.88 (11) |
C4—C5—H5A | 109.5 | N2—C16—H16A | 109.7 |
N1—C5—H5B | 109.5 | C17—C16—H16A | 109.7 |
C4—C5—H5B | 109.5 | N2—C16—H16B | 109.7 |
H5A—C5—H5B | 108.1 | C17—C16—H16B | 109.7 |
N1—C6—N2 | 107.79 (10) | H16A—C16—H16B | 108.2 |
N1—C6—C7 | 110.31 (10) | C18—C17—C16 | 109.33 (12) |
N2—C6—C7 | 110.38 (10) | C18—C17—H17A | 109.8 |
N1—C6—H6 | 109.4 | C16—C17—H17A | 109.8 |
N2—C6—H6 | 109.4 | C18—C17—H17B | 109.8 |
C7—C6—H6 | 109.4 | C16—C17—H17B | 109.8 |
C8—C7—C6 | 128.56 (11) | H17A—C17—H17B | 108.3 |
C8—C7—S2 | 111.23 (9) | N1—C18—C17 | 110.31 (11) |
C6—C7—S2 | 120.21 (9) | N1—C18—H18A | 109.6 |
C7—C8—C9 | 112.47 (11) | C17—C18—H18A | 109.6 |
C7—C8—H8 | 123.8 | N1—C18—H18B | 109.6 |
C9—C8—H8 | 123.8 | C17—C18—H18B | 109.6 |
C10—C9—C8 | 112.67 (12) | H18A—C18—H18B | 108.1 |
C10—C9—H9 | 123.7 | C16—N2—C11 | 109.80 (11) |
C8—C9—H9 | 123.7 | C16—N2—C6 | 110.33 (10) |
C9—C10—S2 | 111.53 (10) | C11—N2—C6 | 112.23 (10) |
C9—C10—H10 | 124.2 | C5—N1—C6 | 112.44 (10) |
S2—C10—H10 | 124.2 | C5—N1—C18 | 109.00 (10) |
N2—C11—C12 | 110.81 (12) | C6—N1—C18 | 111.52 (10) |
N2—C11—H11A | 109.5 | C1—S1—C4 | 92.31 (7) |
C12—C11—H11A | 109.5 | C10—S2—C7 | 92.09 (6) |
N2—C11—H11B | 109.5 | C15—S3—C12 | 92.53 (9) |
C12—C11—H11B | 109.5 | ||
S1—C1—C2—C3 | −0.09 (19) | C12—C11—N2—C16 | −70.25 (15) |
C1—C2—C3—C4 | 0.1 (2) | C12—C11—N2—C6 | 166.64 (11) |
C2—C3—C4—C5 | −175.93 (13) | N1—C6—N2—C16 | 62.86 (13) |
C2—C3—C4—S1 | −0.06 (16) | C7—C6—N2—C16 | −176.61 (11) |
C3—C4—C5—N1 | −147.79 (13) | N1—C6—N2—C11 | −174.34 (11) |
S1—C4—C5—N1 | 36.60 (14) | C7—C6—N2—C11 | −53.80 (14) |
N1—C6—C7—C8 | −122.75 (14) | C4—C5—N1—C6 | −156.52 (10) |
N2—C6—C7—C8 | 118.23 (14) | C4—C5—N1—C18 | 79.28 (14) |
N1—C6—C7—S2 | 57.68 (13) | N2—C6—N1—C5 | 175.78 (10) |
N2—C6—C7—S2 | −61.34 (13) | C7—C6—N1—C5 | 55.20 (13) |
C6—C7—C8—C9 | −179.08 (12) | N2—C6—N1—C18 | −61.43 (13) |
S2—C7—C8—C9 | 0.52 (15) | C7—C6—N1—C18 | 177.99 (10) |
C7—C8—C9—C10 | −0.21 (18) | C17—C18—N1—C5 | −177.05 (12) |
C8—C9—C10—S2 | −0.21 (17) | C17—C18—N1—C6 | 58.21 (15) |
N2—C11—C12—C13 | 131.74 (16) | C2—C1—S1—C4 | 0.05 (14) |
N2—C11—C12—S3 | −47.07 (16) | C3—C4—S1—C1 | 0.01 (11) |
C11—C12—C13—C14 | 177.16 (15) | C5—C4—S1—C1 | 176.27 (11) |
S3—C12—C13—C14 | −3.94 (18) | C9—C10—S2—C7 | 0.43 (12) |
C12—C13—C14—C15 | 3.3 (2) | C8—C7—S2—C10 | −0.55 (11) |
C13—C14—C15—S3 | −1.2 (2) | C6—C7—S2—C10 | 179.09 (11) |
N2—C16—C17—C18 | 55.84 (15) | C14—C15—S3—C12 | −0.98 (16) |
C16—C17—C18—N1 | −54.04 (16) | C13—C12—S3—C15 | 2.86 (13) |
C17—C16—N2—C11 | 174.63 (11) | C11—C12—S3—C15 | −178.15 (13) |
C17—C16—N2—C6 | −61.15 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···S2i | 0.95 | 2.87 | 3.5423 (12) | 129 |
C10—H10···Cg1ii | 0.95 | 2.78 | 3.643 | 151 |
Symmetry codes: (i) x, y−1, z; (ii) x+1/2, −y+3/2, z. |