Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032636/ob2050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032636/ob2050Isup2.hkl |
CCDC reference: 621453
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.053
- wR factor = 0.146
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.30 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.
C18H14FN3O2S2 | Dx = 1.462 Mg m−3 |
Mr = 387.44 | Melting point = 513–514 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.750 (4) Å | Cell parameters from 25 reflections |
b = 6.3720 (13) Å | θ = 10–13° |
c = 31.761 (6) Å | µ = 0.33 mm−1 |
β = 101.55 (3)° | T = 298 K |
V = 3519.5 (12) Å3 | Block, colorless |
Z = 8 | 0.40 × 0.40 × 0.30 mm |
F(000) = 1600 |
Nonius CAD-4 diffractometer | 2562 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.089 |
Graphite monochromator | θmax = 26.0°, θmin = 1.3° |
ω/2θ scans | h = 0→21 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.879, Tmax = 0.907 | l = −39→38 |
3562 measured reflections | 3 standard reflections every 200 reflections |
3449 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0642P)2 + 4.2621P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
3449 reflections | Δρmax = 0.39 e Å−3 |
236 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0034 (4) |
Experimental. Spectroscopic analysis, 1H NMR (CDCl3, δ, p.p.m.): 7.84–7.83(d, 2H), 7.37–7.32(m, 2H), 7.03–7.00 (t, 2H), 6.95–6.93 (d, 2H), 6.96 (s,1H),4.14–4.11 (d, 1H), 3.89–3.86 (d, 1H), 3.84 (s,3H). |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.90946 (5) | 0.58054 (16) | 0.67451 (3) | 0.0657 (3) | |
S2 | 0.72967 (4) | 0.11650 (11) | 0.55477 (2) | 0.0421 (2) | |
F | 0.58643 (14) | 0.6857 (5) | 0.73877 (8) | 0.1073 (10) | |
O1 | 0.86099 (13) | 0.0571 (3) | 0.61388 (8) | 0.0608 (7) | |
O2 | 0.44110 (12) | −0.1486 (3) | 0.39128 (7) | 0.0508 (6) | |
N1 | 0.80742 (13) | 0.3815 (4) | 0.61723 (8) | 0.0407 (6) | |
N2 | 0.69904 (15) | 0.5014 (4) | 0.56896 (9) | 0.0477 (6) | |
N3 | 0.64372 (15) | 0.4388 (4) | 0.53404 (9) | 0.0480 (6) | |
C1 | 0.6419 (2) | 0.6637 (8) | 0.71515 (12) | 0.0679 (11) | |
C2 | 0.6865 (2) | 0.4831 (8) | 0.72159 (11) | 0.0707 (11) | |
H2B | 0.6795 | 0.3826 | 0.7417 | 0.085* | |
C3 | 0.7417 (2) | 0.4588 (6) | 0.69693 (11) | 0.0575 (9) | |
H3B | 0.7729 | 0.3402 | 0.7007 | 0.069* | |
C4 | 0.75155 (17) | 0.6061 (5) | 0.66694 (9) | 0.0427 (7) | |
C5 | 0.70540 (19) | 0.7841 (5) | 0.66169 (11) | 0.0538 (8) | |
H5A | 0.7117 | 0.8851 | 0.6415 | 0.065* | |
C6 | 0.6502 (2) | 0.8117 (7) | 0.68628 (13) | 0.0668 (10) | |
H6A | 0.6192 | 0.9307 | 0.6829 | 0.080* | |
C7 | 0.81308 (17) | 0.5820 (5) | 0.64034 (10) | 0.0446 (7) | |
H7A | 0.8091 | 0.6979 | 0.6197 | 0.054* | |
C8 | 0.92926 (19) | 0.3136 (6) | 0.66297 (11) | 0.0549 (8) | |
H8A | 0.9771 | 0.3053 | 0.6527 | 0.066* | |
H8B | 0.9343 | 0.2293 | 0.6888 | 0.066* | |
C9 | 0.86426 (17) | 0.2327 (5) | 0.62928 (10) | 0.0456 (7) | |
C10 | 0.74685 (16) | 0.3512 (4) | 0.58271 (9) | 0.0378 (6) | |
C11 | 0.65188 (17) | 0.2433 (4) | 0.52302 (10) | 0.0399 (7) | |
C12 | 0.60017 (16) | 0.1392 (4) | 0.48759 (9) | 0.0373 (6) | |
C13 | 0.61607 (18) | −0.0597 (5) | 0.47280 (10) | 0.0444 (7) | |
H13A | 0.6620 | −0.1258 | 0.4850 | 0.053* | |
C14 | 0.56529 (17) | −0.1594 (5) | 0.44058 (10) | 0.0446 (7) | |
H14A | 0.5774 | −0.2904 | 0.4309 | 0.054* | |
C15 | 0.49628 (17) | −0.0643 (4) | 0.42269 (9) | 0.0391 (7) | |
C16 | 0.47926 (18) | 0.1339 (5) | 0.43713 (10) | 0.0455 (7) | |
H16A | 0.4331 | 0.1989 | 0.4251 | 0.055* | |
C17 | 0.53033 (18) | 0.2328 (5) | 0.46893 (10) | 0.0442 (7) | |
H17A | 0.5183 | 0.3647 | 0.4783 | 0.053* | |
C18 | 0.4505 (2) | −0.3635 (5) | 0.37978 (12) | 0.0579 (9) | |
H18A | 0.4082 | −0.4045 | 0.3575 | 0.087* | |
H18B | 0.4519 | −0.4513 | 0.4045 | 0.087* | |
H18C | 0.4978 | −0.3785 | 0.3697 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0480 (5) | 0.0615 (6) | 0.0830 (7) | −0.0093 (4) | 0.0019 (4) | −0.0178 (5) |
S2 | 0.0481 (4) | 0.0278 (4) | 0.0496 (4) | 0.0050 (3) | 0.0076 (3) | −0.0022 (3) |
F | 0.0737 (15) | 0.175 (3) | 0.0807 (16) | 0.0066 (18) | 0.0329 (13) | −0.0354 (19) |
O1 | 0.0570 (14) | 0.0374 (13) | 0.0841 (17) | 0.0113 (10) | 0.0047 (12) | −0.0066 (12) |
O2 | 0.0527 (13) | 0.0358 (12) | 0.0592 (14) | 0.0025 (10) | 0.0000 (11) | −0.0063 (10) |
N1 | 0.0419 (13) | 0.0301 (12) | 0.0496 (14) | 0.0007 (10) | 0.0082 (11) | −0.0029 (11) |
N2 | 0.0535 (15) | 0.0312 (13) | 0.0549 (16) | 0.0065 (12) | 0.0027 (12) | −0.0043 (12) |
N3 | 0.0559 (16) | 0.0323 (13) | 0.0523 (15) | 0.0056 (11) | 0.0022 (12) | −0.0041 (11) |
C1 | 0.049 (2) | 0.106 (3) | 0.048 (2) | 0.000 (2) | 0.0093 (16) | −0.025 (2) |
C2 | 0.066 (2) | 0.100 (3) | 0.046 (2) | −0.003 (2) | 0.0107 (18) | 0.011 (2) |
C3 | 0.0547 (19) | 0.065 (2) | 0.0522 (19) | 0.0103 (17) | 0.0086 (16) | 0.0111 (17) |
C4 | 0.0464 (16) | 0.0372 (15) | 0.0412 (16) | −0.0011 (13) | 0.0009 (13) | −0.0069 (14) |
C5 | 0.059 (2) | 0.0416 (18) | 0.058 (2) | 0.0012 (15) | 0.0043 (16) | −0.0067 (15) |
C6 | 0.058 (2) | 0.065 (2) | 0.074 (3) | 0.0125 (18) | 0.0035 (19) | −0.023 (2) |
C7 | 0.0512 (17) | 0.0326 (16) | 0.0483 (17) | −0.0046 (13) | 0.0057 (14) | −0.0030 (13) |
C8 | 0.0477 (18) | 0.058 (2) | 0.058 (2) | 0.0050 (16) | 0.0074 (15) | 0.0049 (17) |
C9 | 0.0432 (16) | 0.0433 (18) | 0.0525 (18) | 0.0011 (14) | 0.0149 (14) | 0.0049 (15) |
C10 | 0.0437 (15) | 0.0276 (14) | 0.0434 (16) | 0.0015 (12) | 0.0116 (13) | −0.0009 (12) |
C11 | 0.0458 (16) | 0.0306 (14) | 0.0461 (17) | 0.0055 (12) | 0.0157 (13) | 0.0037 (13) |
C12 | 0.0464 (16) | 0.0300 (14) | 0.0367 (15) | 0.0007 (12) | 0.0111 (12) | −0.0006 (12) |
C13 | 0.0459 (17) | 0.0341 (16) | 0.0533 (18) | 0.0082 (13) | 0.0101 (14) | −0.0043 (13) |
C14 | 0.0524 (18) | 0.0301 (15) | 0.0519 (18) | 0.0081 (13) | 0.0117 (14) | −0.0063 (13) |
C15 | 0.0484 (16) | 0.0292 (14) | 0.0407 (16) | −0.0002 (12) | 0.0109 (13) | 0.0010 (12) |
C16 | 0.0495 (17) | 0.0337 (15) | 0.0510 (17) | 0.0096 (13) | 0.0043 (14) | 0.0018 (14) |
C17 | 0.0564 (18) | 0.0272 (14) | 0.0494 (18) | 0.0091 (13) | 0.0114 (14) | −0.0010 (13) |
C18 | 0.060 (2) | 0.0362 (17) | 0.074 (2) | −0.0042 (15) | 0.0046 (17) | −0.0128 (17) |
S1—C8 | 1.789 (4) | C5—C6 | 1.382 (5) |
S1—C7 | 1.833 (3) | C5—H5A | 0.9300 |
S2—C10 | 1.735 (3) | C6—H6A | 0.9300 |
S2—C11 | 1.737 (3) | C7—H7A | 0.9800 |
F—C1 | 1.360 (4) | C8—C9 | 1.499 (5) |
O1—C9 | 1.218 (4) | C8—H8A | 0.9700 |
O2—C15 | 1.361 (4) | C8—H8B | 0.9700 |
O2—C18 | 1.436 (4) | C11—C12 | 1.462 (4) |
N1—C9 | 1.381 (4) | C12—C17 | 1.396 (4) |
N1—C10 | 1.387 (4) | C12—C13 | 1.400 (4) |
N1—C7 | 1.467 (4) | C13—C14 | 1.376 (4) |
N2—C10 | 1.295 (4) | C13—H13A | 0.9300 |
N2—N3 | 1.384 (4) | C14—C15 | 1.383 (4) |
N3—C11 | 1.310 (4) | C14—H14A | 0.9300 |
C1—C6 | 1.343 (6) | C15—C16 | 1.397 (4) |
C1—C2 | 1.389 (6) | C16—C17 | 1.368 (4) |
C2—C3 | 1.380 (5) | C16—H16A | 0.9300 |
C2—H2B | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.373 (4) | C18—H18A | 0.9600 |
C3—H3B | 0.9300 | C18—H18B | 0.9600 |
C4—C5 | 1.389 (4) | C18—H18C | 0.9600 |
C4—C7 | 1.516 (4) | ||
C8—S1—C7 | 94.71 (15) | S1—C8—H8B | 110.0 |
C10—S2—C11 | 86.19 (14) | H8A—C8—H8B | 108.4 |
C15—O2—C18 | 117.4 (2) | O1—C9—N1 | 123.1 (3) |
C9—N1—C10 | 122.1 (3) | O1—C9—C8 | 124.8 (3) |
C9—N1—C7 | 119.1 (3) | N1—C9—C8 | 112.1 (3) |
C10—N1—C7 | 118.8 (2) | N2—C10—N1 | 121.0 (3) |
C10—N2—N3 | 111.6 (2) | N2—C10—S2 | 115.4 (2) |
C11—N3—N2 | 112.9 (3) | N1—C10—S2 | 123.6 (2) |
C6—C1—F | 119.6 (4) | N3—C11—C12 | 123.5 (3) |
C6—C1—C2 | 123.1 (3) | N3—C11—S2 | 113.9 (2) |
F—C1—C2 | 117.3 (4) | C12—C11—S2 | 122.6 (2) |
C3—C2—C1 | 117.2 (4) | C17—C12—C13 | 117.8 (3) |
C3—C2—H2B | 121.4 | C17—C12—C11 | 120.0 (3) |
C1—C2—H2B | 121.4 | C13—C12—C11 | 122.1 (3) |
C4—C3—C2 | 121.4 (4) | C14—C13—C12 | 121.4 (3) |
C4—C3—H3B | 119.3 | C14—C13—H13A | 119.3 |
C2—C3—H3B | 119.3 | C12—C13—H13A | 119.3 |
C3—C4—C5 | 119.2 (3) | C13—C14—C15 | 119.8 (3) |
C3—C4—C7 | 121.5 (3) | C13—C14—H14A | 120.1 |
C5—C4—C7 | 119.3 (3) | C15—C14—H14A | 120.1 |
C4—C5—C6 | 120.3 (3) | O2—C15—C14 | 125.2 (3) |
C4—C5—H5A | 119.9 | O2—C15—C16 | 115.2 (3) |
C6—C5—H5A | 119.9 | C14—C15—C16 | 119.6 (3) |
C1—C6—C5 | 118.9 (4) | C17—C16—C15 | 120.2 (3) |
C1—C6—H6A | 120.6 | C17—C16—H16A | 119.9 |
C5—C6—H6A | 120.6 | C15—C16—H16A | 119.9 |
N1—C7—C4 | 112.5 (2) | C16—C17—C12 | 121.1 (3) |
N1—C7—S1 | 104.7 (2) | C16—C17—H17A | 119.4 |
C4—C7—S1 | 111.2 (2) | C12—C17—H17A | 119.4 |
N1—C7—H7A | 109.5 | O2—C18—H18A | 109.5 |
C4—C7—H7A | 109.5 | O2—C18—H18B | 109.5 |
S1—C7—H7A | 109.5 | H18A—C18—H18B | 109.5 |
C9—C8—S1 | 108.5 (2) | O2—C18—H18C | 109.5 |
C9—C8—H8A | 110.0 | H18A—C18—H18C | 109.5 |
S1—C8—H8A | 110.0 | H18B—C18—H18C | 109.5 |
C9—C8—H8B | 110.0 | ||
C10—N2—N3—C11 | 0.3 (4) | N3—N2—C10—N1 | 179.3 (2) |
C6—C1—C2—C3 | 0.4 (6) | N3—N2—C10—S2 | −0.2 (3) |
F—C1—C2—C3 | 178.6 (3) | C9—N1—C10—N2 | −172.2 (3) |
C1—C2—C3—C4 | −0.7 (6) | C7—N1—C10—N2 | 4.9 (4) |
C2—C3—C4—C5 | 0.6 (5) | C9—N1—C10—S2 | 7.2 (4) |
C2—C3—C4—C7 | 178.9 (3) | C7—N1—C10—S2 | −175.7 (2) |
C3—C4—C5—C6 | −0.2 (5) | C11—S2—C10—N2 | 0.0 (2) |
C7—C4—C5—C6 | −178.5 (3) | C11—S2—C10—N1 | −179.4 (3) |
F—C1—C6—C5 | −178.2 (3) | N2—N3—C11—C12 | 179.1 (3) |
C2—C1—C6—C5 | 0.0 (6) | N2—N3—C11—S2 | −0.3 (3) |
C4—C5—C6—C1 | −0.1 (5) | C10—S2—C11—N3 | 0.2 (2) |
C9—N1—C7—C4 | −111.6 (3) | C10—S2—C11—C12 | −179.2 (2) |
C10—N1—C7—C4 | 71.3 (3) | N3—C11—C12—C17 | −12.5 (4) |
C9—N1—C7—S1 | 9.3 (3) | S2—C11—C12—C17 | 166.9 (2) |
C10—N1—C7—S1 | −167.9 (2) | N3—C11—C12—C13 | 171.1 (3) |
C3—C4—C7—N1 | 54.8 (4) | S2—C11—C12—C13 | −9.5 (4) |
C5—C4—C7—N1 | −127.0 (3) | C17—C12—C13—C14 | 0.8 (4) |
C3—C4—C7—S1 | −62.2 (3) | C11—C12—C13—C14 | 177.3 (3) |
C5—C4—C7—S1 | 116.0 (3) | C12—C13—C14—C15 | −1.1 (5) |
C8—S1—C7—N1 | −8.0 (2) | C18—O2—C15—C14 | 8.7 (4) |
C8—S1—C7—C4 | 113.7 (2) | C18—O2—C15—C16 | −171.1 (3) |
C7—S1—C8—C9 | 5.5 (2) | C13—C14—C15—O2 | −178.9 (3) |
C10—N1—C9—O1 | −8.4 (5) | C13—C14—C15—C16 | 0.9 (4) |
C7—N1—C9—O1 | 174.5 (3) | O2—C15—C16—C17 | 179.4 (3) |
C10—N1—C9—C8 | 171.4 (3) | C14—C15—C16—C17 | −0.4 (4) |
C7—N1—C9—C8 | −5.7 (4) | C15—C16—C17—C12 | 0.1 (5) |
S1—C8—C9—O1 | 178.7 (3) | C13—C12—C17—C16 | −0.3 (4) |
S1—C8—C9—N1 | −1.2 (3) | C11—C12—C17—C16 | −176.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O1i | 0.98 | 2.49 | 3.299 (4) | 140 |
C13—H13A···S2 | 0.93 | 2.77 | 3.163 (3) | 107 |
Symmetry code: (i) x, y+1, z. |