Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020915/bx2009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020915/bx2009Isup2.hkl |
CCDC reference: 613616
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. CG .. 2.92 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku,1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).
C19H17NOS2 | F(000) = 712 |
Mr = 339.46 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 12911 reflections |
a = 15.321 (6) Å | θ = 3.3–27.5° |
b = 6.654 (2) Å | µ = 0.31 mm−1 |
c = 16.792 (5) Å | T = 298 K |
β = 90.361 (15)° | Prism, colourless |
V = 1711.7 (10) Å3 | 0.31 × 0.28 × 0.25 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3045 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.028 |
ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.905, Tmax = 0.924 | k = −8→7 |
16160 measured reflections | l = −21→21 |
3933 independent reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.211P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max = 0.001 |
wR(F2) = 0.100 | Δρmax = 0.18 e Å−3 |
S = 1.06 | Δρmin = −0.19 e Å−3 |
3933 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
213 parameters | Extinction coefficient: 0.009 (1) |
0 restraints |
Experimental. 2,6-Bis(phenylthiomethyl)-4-(tetrahydro-2-pyranoxy)pyridine: 1H NMR (500 MHz, CDCl3): δ 7.31 (m, 4 H), 7.22 (m, 4 H), 7.13 (m, 2 H), 6.86 (s, 2 H), 5.33 (t, 1 H), 4.18 (s, 4 H), 3.51–3.69 (m, 2 H), 1.76–1.80 (m, 3 H), 1.56–1.64 (m, 3 H); 13 C NMR (125?MHz, CDCl3): δ 164.3, 158.7, 136.1, 129.4, 128.7, 126.1, 109.3, 95.7, 61.8, 40.3, 29.7, 24.9, 18.2. 2,6-Bis(phenylthiomethyl)pyridinium-4-olate: 1H NMR (500?MHz, DMSO-d6): δ 10.52 (s, 1 H), 7.33 (t, 4 H), 7. 25 (m, 4 H), 7.16 (t, 2 H), 6.69 (s, 2 H), 4.17 (s, 4 H); 13 C NMR (125?MHz, DMSO-d6): δ 136.5, 129.4, 128.5, 126.2, 110.5, 38.2. |
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 | 0.54529 (9) | 0.6284 (2) | 0.15671 (8) | 0.0426 (3) | |
C2 | 0.54659 (11) | 0.4239 (2) | 0.15527 (10) | 0.0538 (4) | |
H2 | 0.5899 | 0.3555 | 0.1833 | 0.065* | |
C3 | 0.48295 (11) | 0.3129 (2) | 0.11175 (11) | 0.0589 (5) | |
C4 | 0.41623 (11) | 0.4277 (2) | 0.07395 (10) | 0.0511 (4) | |
H4 | 0.3719 | 0.3621 | 0.0462 | 0.061* | |
C5 | 0.41623 (9) | 0.63165 (19) | 0.07767 (8) | 0.0415 (3) | |
C6 | 0.61113 (10) | 0.7556 (2) | 0.19905 (9) | 0.0516 (4) | |
H6A | 0.6409 | 0.6742 | 0.2387 | 0.062* | |
H6B | 0.581 | 0.8629 | 0.2267 | 0.062* | |
C7 | 0.76328 (10) | 0.6648 (3) | 0.11150 (8) | 0.0506 (4) | |
C8 | 0.81331 (12) | 0.6858 (3) | 0.04318 (10) | 0.0681 (5) | |
H8 | 0.8068 | 0.7993 | 0.0114 | 0.082* | |
C9 | 0.87252 (13) | 0.5392 (4) | 0.02229 (11) | 0.0819 (6) | |
H9 | 0.9063 | 0.5563 | −0.023 | 0.098* | |
C10 | 0.88223 (13) | 0.3696 (4) | 0.06705 (12) | 0.0773 (6) | |
H10 | 0.9217 | 0.2707 | 0.052 | 0.093* | |
C11 | 0.83341 (12) | 0.3466 (3) | 0.13421 (12) | 0.0708 (5) | |
H11 | 0.8397 | 0.2311 | 0.1649 | 0.085* | |
C12 | 0.77473 (11) | 0.4936 (3) | 0.15692 (10) | 0.0594 (4) | |
H12 | 0.7426 | 0.4769 | 0.2033 | 0.071* | |
C13 | 0.34894 (10) | 0.7630 (2) | 0.04005 (9) | 0.0493 (3) | |
H13A | 0.3076 | 0.679 | 0.0115 | 0.059* | |
H13B | 0.3772 | 0.8491 | 0.0014 | 0.059* | |
C14 | 0.20064 (10) | 0.7658 (3) | 0.13913 (9) | 0.0538 (4) | |
C15 | 0.21274 (13) | 0.5765 (3) | 0.17162 (10) | 0.0664 (5) | |
H15 | 0.2688 | 0.5245 | 0.177 | 0.08* | |
C16 | 0.14192 (16) | 0.4644 (4) | 0.19608 (12) | 0.0870 (7) | |
H16 | 0.1504 | 0.3369 | 0.2174 | 0.104* | |
C17 | 0.05952 (17) | 0.5403 (5) | 0.18901 (13) | 0.0979 (9) | |
H17 | 0.0121 | 0.4639 | 0.2055 | 0.117* | |
C18 | 0.04604 (13) | 0.7284 (5) | 0.15768 (13) | 0.0944 (8) | |
H18 | −0.0103 | 0.7795 | 0.1535 | 0.113* | |
C19 | 0.11694 (12) | 0.8430 (4) | 0.13217 (11) | 0.0720 (5) | |
H19 | 0.108 | 0.9702 | 0.1106 | 0.086* | |
N1 | 0.48122 (8) | 0.72789 (17) | 0.11763 (7) | 0.0416 (3) | |
S1 | 0.69152 (3) | 0.86479 (6) | 0.13352 (3) | 0.05995 (14) | |
S2 | 0.28902 (3) | 0.92065 (6) | 0.10980 (3) | 0.05605 (14) | |
O1 | 0.48544 (10) | 0.12453 (16) | 0.10770 (12) | 0.0997 (6) | |
H1N | 0.4814 (10) | 0.858 (3) | 0.1181 (9) | 0.055 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0469 (8) | 0.0343 (6) | 0.0468 (7) | 0.0013 (6) | 0.0110 (6) | 0.0028 (6) |
C2 | 0.0529 (9) | 0.0351 (7) | 0.0738 (10) | 0.0077 (6) | 0.0153 (8) | 0.0144 (7) |
C3 | 0.0612 (10) | 0.0267 (7) | 0.0892 (12) | −0.0030 (6) | 0.0277 (9) | 0.0022 (7) |
C4 | 0.0554 (9) | 0.0321 (7) | 0.0661 (9) | −0.0107 (6) | 0.0159 (7) | −0.0076 (6) |
C5 | 0.0469 (8) | 0.0320 (6) | 0.0458 (7) | −0.0052 (6) | 0.0115 (6) | −0.0015 (6) |
C6 | 0.0532 (9) | 0.0528 (9) | 0.0490 (8) | 0.0031 (7) | 0.0019 (7) | −0.0035 (7) |
C7 | 0.0413 (8) | 0.0658 (10) | 0.0447 (7) | −0.0101 (7) | −0.0057 (6) | 0.0014 (7) |
C8 | 0.0585 (11) | 0.0972 (14) | 0.0486 (8) | −0.0121 (10) | −0.0016 (7) | 0.0134 (9) |
C9 | 0.0594 (12) | 0.135 (2) | 0.0510 (9) | −0.0051 (12) | 0.0077 (8) | −0.0073 (12) |
C10 | 0.0572 (11) | 0.1047 (16) | 0.0699 (11) | 0.0098 (11) | −0.0044 (9) | −0.0180 (12) |
C11 | 0.0552 (11) | 0.0792 (12) | 0.0780 (12) | 0.0051 (9) | −0.0056 (9) | 0.0041 (10) |
C12 | 0.0499 (9) | 0.0734 (11) | 0.0550 (9) | −0.0009 (8) | 0.0033 (7) | 0.0079 (8) |
C13 | 0.0514 (9) | 0.0476 (8) | 0.0490 (8) | −0.0030 (7) | 0.0046 (6) | 0.0021 (6) |
C14 | 0.0470 (9) | 0.0695 (10) | 0.0450 (7) | −0.0028 (8) | 0.0009 (6) | −0.0090 (7) |
C15 | 0.0634 (11) | 0.0788 (12) | 0.0571 (9) | −0.0104 (9) | 0.0022 (8) | 0.0094 (9) |
C16 | 0.0892 (17) | 0.1092 (18) | 0.0628 (11) | −0.0378 (14) | 0.0044 (10) | 0.0103 (11) |
C17 | 0.0766 (16) | 0.159 (3) | 0.0579 (11) | −0.0503 (17) | 0.0089 (10) | −0.0102 (14) |
C18 | 0.0460 (11) | 0.168 (3) | 0.0698 (12) | −0.0029 (14) | 0.0048 (9) | −0.0305 (16) |
C19 | 0.0516 (10) | 0.1016 (15) | 0.0628 (10) | 0.0107 (10) | 0.0002 (8) | −0.0171 (10) |
N1 | 0.0488 (7) | 0.0233 (5) | 0.0527 (7) | −0.0007 (5) | 0.0034 (5) | −0.0008 (5) |
S1 | 0.0574 (3) | 0.0505 (2) | 0.0719 (3) | −0.01131 (19) | −0.0018 (2) | 0.00729 (19) |
S2 | 0.0520 (2) | 0.0436 (2) | 0.0727 (3) | 0.00333 (17) | 0.00483 (19) | −0.00267 (18) |
O1 | 0.0951 (11) | 0.0206 (5) | 0.1838 (17) | −0.0011 (6) | 0.0272 (11) | 0.0017 (7) |
C1—N1 | 1.3507 (19) | C10—C11 | 1.366 (3) |
C1—C2 | 1.361 (2) | C10—H10 | 0.93 |
C1—C6 | 1.494 (2) | C11—C12 | 1.384 (3) |
C2—C3 | 1.422 (2) | C11—H11 | 0.93 |
C2—H2 | 0.93 | C12—H12 | 0.93 |
C3—O1 | 1.2555 (18) | C13—S2 | 1.8242 (15) |
C3—C4 | 1.422 (2) | C13—H13A | 0.97 |
C4—C5 | 1.3585 (19) | C13—H13B | 0.97 |
C4—H4 | 0.93 | C14—C15 | 1.385 (3) |
C5—N1 | 1.3577 (18) | C14—C19 | 1.386 (2) |
C5—C13 | 1.489 (2) | C14—S2 | 1.7735 (17) |
C6—S1 | 1.8091 (16) | C15—C16 | 1.381 (3) |
C6—H6A | 0.97 | C15—H15 | 0.93 |
C6—H6B | 0.97 | C16—C17 | 1.364 (4) |
C7—C12 | 1.382 (2) | C16—H16 | 0.93 |
C7—C8 | 1.391 (2) | C17—C18 | 1.373 (4) |
C7—S1 | 1.7668 (18) | C17—H17 | 0.93 |
C8—C9 | 1.379 (3) | C18—C19 | 1.397 (3) |
C8—H8 | 0.93 | C18—H18 | 0.93 |
C9—C10 | 1.363 (3) | C19—H19 | 0.93 |
C9—H9 | 0.93 | N1—H1N | 0.868 (19) |
N1—C1—C2 | 119.48 (15) | C10—C11—H11 | 119.7 |
N1—C1—C6 | 116.10 (13) | C12—C11—H11 | 119.7 |
C2—C1—C6 | 124.42 (15) | C7—C12—C11 | 120.74 (16) |
C1—C2—C3 | 121.23 (15) | C7—C12—H12 | 119.6 |
C1—C2—H2 | 119.4 | C11—C12—H12 | 119.6 |
C3—C2—H2 | 119.4 | C5—C13—S2 | 114.52 (10) |
O1—C3—C2 | 121.70 (18) | C5—C13—H13A | 108.6 |
O1—C3—C4 | 122.27 (18) | S2—C13—H13A | 108.6 |
C2—C3—C4 | 116.03 (13) | C5—C13—H13B | 108.6 |
C5—C4—C3 | 121.09 (15) | S2—C13—H13B | 108.6 |
C5—C4—H4 | 119.5 | H13A—C13—H13B | 107.6 |
C3—C4—H4 | 119.5 | C15—C14—C19 | 119.45 (17) |
N1—C5—C4 | 119.58 (14) | C15—C14—S2 | 122.50 (13) |
N1—C5—C13 | 115.87 (12) | C19—C14—S2 | 117.99 (15) |
C4—C5—C13 | 124.55 (15) | C16—C15—C14 | 120.3 (2) |
C1—C6—S1 | 113.48 (10) | C16—C15—H15 | 119.8 |
C1—C6—H6A | 108.9 | C14—C15—H15 | 119.8 |
S1—C6—H6A | 108.9 | C17—C16—C15 | 120.2 (2) |
C1—C6—H6B | 108.9 | C17—C16—H16 | 119.9 |
S1—C6—H6B | 108.9 | C15—C16—H16 | 119.9 |
H6A—C6—H6B | 107.7 | C16—C17—C18 | 120.5 (2) |
C12—C7—C8 | 118.00 (17) | C16—C17—H17 | 119.7 |
C12—C7—S1 | 125.63 (12) | C18—C17—H17 | 119.7 |
C8—C7—S1 | 116.36 (14) | C17—C18—C19 | 120.0 (2) |
C9—C8—C7 | 120.39 (19) | C17—C18—H18 | 120 |
C9—C8—H8 | 119.8 | C19—C18—H18 | 120 |
C7—C8—H8 | 119.8 | C14—C19—C18 | 119.6 (2) |
C10—C9—C8 | 120.97 (17) | C14—C19—H19 | 120.2 |
C10—C9—H9 | 119.5 | C18—C19—H19 | 120.2 |
C8—C9—H9 | 119.5 | C1—N1—C5 | 122.50 (12) |
C9—C10—C11 | 119.3 (2) | C1—N1—H1N | 118.9 (11) |
C9—C10—H10 | 120.3 | C5—N1—H1N | 118.6 (11) |
C11—C10—H10 | 120.3 | C7—S1—C6 | 104.58 (8) |
C10—C11—C12 | 120.5 (2) | C14—S2—C13 | 103.45 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.87 (2) | 1.78 (2) | 2.645 (2) | 173.6 (15) |
C13—H13A···Cgii | 0.97 | 2.92 | 3.881 (2) | 171 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z. |