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
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.082
- Data-to-parameter ratio = 27.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C2 - C3 .. 13.85 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C4 .. 9.27 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 .. 12.78 su
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.410 From the CIF: _refine_ls_abs_structure_Flack_su 0.040 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.41 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.25 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C4 .. 6.62 su PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H20 N2 S3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 31.99 From the CIF: _reflns_number_total 5679 Count of symmetry unique reflns 3196 Completeness (_total/calc) 177.69% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2483 Fraction of Friedel pairs measured 0.777 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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. |
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