In the title compound, C
22H
15ClFN
5S, molecules are linked by N—H
N hydrogen bonds into chains, which in turn are linked into sheets by C—H
π interactions.
Supporting information
CCDC reference: 651376
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.120
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 35.00 A 3
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C22H15ClFN5S | F(000) = 1792 |
Mr = 435.9 | Dx = 1.423 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 25.583 (5) Å | θ = 9.9–18.1° |
b = 9.9377 (14) Å | µ = 0.32 mm−1 |
c = 20.207 (3) Å | T = 293 K |
β = 127.599 (12)° | Prism, colourless |
V = 4070.3 (12) Å3 | 0.36 × 0.33 × 0.24 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.043 |
ω/2θ scans | θmax = 26.3°, θmin = 2.3° |
Absorption correction: ψ scan (North et al., 1968) | h = −31→0 |
Tmin = 0.894, Tmax = 0.927 | k = −12→0 |
4033 measured reflections | l = −19→25 |
3948 independent reflections | 3 standard reflections every 120 min |
2473 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0528P)2 + 1.437P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.121 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.21 e Å−3 |
3948 reflections | Δρmin = −0.29 e Å−3 |
276 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C2 | 0.73303 (12) | 0.1194 (2) | 0.74358 (15) | 0.0387 (6) | |
C4 | 0.60582 (14) | 0.1607 (3) | 0.76226 (19) | 0.0565 (8) | |
H4 | 0.5652 | 0.1785 | 0.7114 | 0.068* | |
C5 | 0.61246 (16) | 0.1521 (3) | 0.8349 (2) | 0.0648 (9) | |
H5A | 0.5755 | 0.1632 | 0.8329 | 0.078* | |
C6 | 0.67349 (17) | 0.1272 (3) | 0.9115 (2) | 0.0650 (9) | |
H6 | 0.6761 | 0.1226 | 0.9594 | 0.078* | |
C7 | 0.72965 (15) | 0.1093 (3) | 0.91821 (17) | 0.0542 (7) | |
H7 | 0.7704 | 0.0944 | 0.9695 | 0.065* | |
C8 | 0.72274 (12) | 0.1146 (2) | 0.84460 (16) | 0.0406 (6) | |
C9 | 0.66244 (12) | 0.1418 (3) | 0.76784 (15) | 0.0421 (6) | |
C10 | 0.76349 (12) | 0.1167 (2) | 0.70061 (15) | 0.0393 (6) | |
C11 | 0.79438 (13) | 0.0027 (3) | 0.69954 (16) | 0.0472 (7) | |
H11 | 0.7964 | −0.0749 | 0.7268 | 0.057* | |
C12 | 0.82210 (13) | 0.0034 (3) | 0.65850 (17) | 0.0531 (7) | |
H12 | 0.8417 | −0.0737 | 0.6566 | 0.064* | |
C13 | 0.82016 (13) | 0.1196 (3) | 0.62069 (16) | 0.0503 (7) | |
C14 | 0.78944 (15) | 0.2329 (3) | 0.61965 (18) | 0.0614 (8) | |
H14 | 0.7879 | 0.3102 | 0.5926 | 0.074* | |
C15 | 0.76056 (14) | 0.2310 (3) | 0.65947 (17) | 0.0534 (7) | |
H15 | 0.739 | 0.3072 | 0.6585 | 0.064* | |
C16 | 0.83863 (12) | 0.0835 (3) | 0.89070 (15) | 0.0415 (6) | |
H16A | 0.8571 | 0.0466 | 0.8646 | 0.050* | |
H16B | 0.8474 | 0.0203 | 0.933 | 0.050* | |
C17 | 0.87199 (11) | 0.2149 (2) | 0.93180 (14) | 0.0363 (6) | |
C18 | 0.91232 (11) | 0.4387 (3) | 0.97000 (14) | 0.0357 (6) | |
C19 | 0.96178 (12) | 0.6568 (3) | 1.03957 (15) | 0.0396 (6) | |
C20 | 0.99454 (13) | 0.6191 (3) | 1.12250 (16) | 0.0523 (7) | |
H20 | 0.9934 | 0.5301 | 1.1357 | 0.063* | |
C21 | 1.02871 (15) | 0.7142 (4) | 1.18505 (18) | 0.0630 (9) | |
H21 | 1.0507 | 0.6881 | 1.2403 | 0.076* | |
C22 | 1.03085 (15) | 0.8469 (4) | 1.1672 (2) | 0.0662 (9) | |
H22 | 1.0537 | 0.9098 | 1.2101 | 0.079* | |
C23 | 0.99901 (14) | 0.8862 (3) | 1.08553 (19) | 0.0572 (8) | |
H23 | 0.9999 | 0.9754 | 1.0723 | 0.069* | |
C24 | 0.96614 (12) | 0.7904 (3) | 1.02453 (16) | 0.0452 (7) | |
Cl1 | 0.86142 (4) | 0.12627 (11) | 0.57715 (5) | 0.0822 (3) | |
F1 | 0.93480 (8) | 0.82834 (16) | 0.94364 (10) | 0.0615 (5) | |
N1 | 0.76745 (10) | 0.0981 (2) | 0.82778 (12) | 0.0382 (5) | |
N2 | 0.67032 (10) | 0.1453 (2) | 0.70541 (12) | 0.0440 (5) | |
N3 | 0.91089 (11) | 0.2316 (2) | 1.01154 (13) | 0.0468 (6) | |
N4 | 0.93564 (11) | 0.3616 (2) | 1.03505 (12) | 0.0463 (6) | |
N5 | 0.92497 (10) | 0.5713 (2) | 0.97037 (13) | 0.0417 (5) | |
S1 | 0.86067 (3) | 0.35519 (7) | 0.87464 (4) | 0.0449 (2) | |
H5 | 0.9030 (12) | 0.609 (2) | 0.9211 (15) | 0.043 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0433 (15) | 0.0292 (14) | 0.0404 (13) | −0.0032 (11) | 0.0240 (12) | −0.0051 (11) |
C4 | 0.0458 (16) | 0.0549 (19) | 0.0637 (18) | −0.0070 (14) | 0.0307 (15) | −0.0166 (15) |
C5 | 0.064 (2) | 0.071 (2) | 0.080 (2) | −0.0102 (17) | 0.0545 (19) | −0.0149 (18) |
C6 | 0.081 (2) | 0.069 (2) | 0.070 (2) | −0.0092 (18) | 0.058 (2) | −0.0048 (17) |
C7 | 0.0640 (19) | 0.0527 (19) | 0.0510 (17) | −0.0032 (15) | 0.0378 (15) | 0.0000 (14) |
C8 | 0.0458 (15) | 0.0307 (14) | 0.0475 (15) | −0.0071 (11) | 0.0296 (13) | −0.0069 (11) |
C9 | 0.0440 (14) | 0.0359 (14) | 0.0450 (14) | −0.0052 (12) | 0.0265 (13) | −0.0111 (12) |
C10 | 0.0417 (14) | 0.0335 (15) | 0.0372 (13) | −0.0021 (11) | 0.0213 (12) | −0.0053 (11) |
C11 | 0.0520 (16) | 0.0367 (15) | 0.0519 (16) | −0.0020 (12) | 0.0312 (14) | −0.0034 (12) |
C12 | 0.0519 (17) | 0.0508 (18) | 0.0586 (17) | −0.0032 (14) | 0.0348 (15) | −0.0132 (15) |
C13 | 0.0479 (16) | 0.063 (2) | 0.0428 (15) | −0.0109 (15) | 0.0288 (13) | −0.0131 (14) |
C14 | 0.080 (2) | 0.055 (2) | 0.0577 (18) | 0.0034 (17) | 0.0463 (17) | 0.0097 (15) |
C15 | 0.0682 (19) | 0.0432 (16) | 0.0547 (17) | 0.0116 (15) | 0.0405 (16) | 0.0070 (14) |
C16 | 0.0399 (14) | 0.0336 (14) | 0.0448 (14) | 0.0034 (12) | 0.0227 (12) | 0.0029 (12) |
C17 | 0.0351 (13) | 0.0329 (14) | 0.0378 (13) | 0.0044 (11) | 0.0206 (11) | 0.0049 (11) |
C18 | 0.0289 (12) | 0.0418 (15) | 0.0342 (13) | −0.0004 (11) | 0.0181 (11) | 0.0003 (11) |
C19 | 0.0331 (13) | 0.0436 (16) | 0.0420 (14) | −0.0032 (12) | 0.0228 (11) | −0.0030 (12) |
C20 | 0.0491 (16) | 0.0551 (19) | 0.0427 (15) | −0.0067 (14) | 0.0229 (13) | −0.0022 (14) |
C21 | 0.0560 (18) | 0.077 (2) | 0.0437 (16) | −0.0158 (17) | 0.0243 (15) | −0.0141 (16) |
C22 | 0.0524 (18) | 0.072 (2) | 0.064 (2) | −0.0222 (17) | 0.0302 (16) | −0.0270 (18) |
C23 | 0.0491 (17) | 0.0473 (18) | 0.071 (2) | −0.0124 (14) | 0.0349 (16) | −0.0125 (15) |
C24 | 0.0351 (13) | 0.0480 (17) | 0.0470 (15) | −0.0031 (13) | 0.0221 (12) | −0.0027 (13) |
Cl1 | 0.0785 (6) | 0.1167 (8) | 0.0773 (6) | −0.0246 (5) | 0.0608 (5) | −0.0249 (5) |
F1 | 0.0681 (11) | 0.0432 (10) | 0.0561 (10) | −0.0034 (8) | 0.0290 (9) | 0.0065 (8) |
N1 | 0.0386 (11) | 0.0337 (12) | 0.0381 (11) | −0.0005 (9) | 0.0213 (10) | −0.0006 (9) |
N2 | 0.0396 (12) | 0.0441 (13) | 0.0408 (12) | −0.0013 (10) | 0.0207 (10) | −0.0103 (10) |
N3 | 0.0533 (13) | 0.0401 (13) | 0.0411 (13) | −0.0051 (11) | 0.0257 (11) | 0.0025 (10) |
N4 | 0.0547 (14) | 0.0420 (13) | 0.0338 (11) | −0.0076 (11) | 0.0226 (10) | 0.0019 (10) |
N5 | 0.0445 (13) | 0.0352 (13) | 0.0336 (12) | −0.0040 (10) | 0.0177 (10) | 0.0032 (10) |
S1 | 0.0481 (4) | 0.0379 (4) | 0.0332 (3) | −0.0028 (3) | 0.0169 (3) | 0.0022 (3) |
Geometric parameters (Å, º) top
C2—N2 | 1.313 (3) | C19—C24 | 1.381 (4) |
C2—N1 | 1.374 (3) | C19—C20 | 1.392 (3) |
C2—C10 | 1.479 (4) | C19—N5 | 1.399 (3) |
C4—C5 | 1.373 (4) | C20—C21 | 1.381 (4) |
C4—C9 | 1.395 (4) | C21—C22 | 1.378 (4) |
C5—C6 | 1.395 (4) | C22—C23 | 1.378 (4) |
C6—C7 | 1.370 (4) | C23—C24 | 1.367 (4) |
C7—C8 | 1.387 (4) | C24—F1 | 1.363 (3) |
C8—N1 | 1.388 (3) | N3—N4 | 1.389 (3) |
C8—C9 | 1.393 (3) | N5—H5 | 0.87 (2) |
C9—N2 | 1.394 (3) | C4—H4 | 0.9300 |
C10—C15 | 1.382 (4) | C5—H5A | 0.9300 |
C10—C11 | 1.389 (3) | C6—H6 | 0.9300 |
C11—C12 | 1.381 (4) | C7—H7 | 0.9300 |
C12—C13 | 1.369 (4) | C11—H11 | 0.9300 |
C13—C14 | 1.366 (4) | C12—H12 | 0.9300 |
C13—Cl1 | 1.740 (3) | C14—H14 | 0.9300 |
C14—C15 | 1.385 (4) | C15—H15 | 0.9300 |
C16—N1 | 1.459 (3) | C16—H16A | 0.9700 |
C16—C17 | 1.503 (3) | C16—H16B | 0.9700 |
C17—N3 | 1.288 (3) | C20—H20 | 0.9300 |
C17—S1 | 1.719 (2) | C21—H21 | 0.9300 |
C18—N4 | 1.309 (3) | C22—H22 | 0.9300 |
C18—N5 | 1.356 (3) | C23—H23 | 0.9300 |
C18—S1 | 1.744 (2) | | |
| | | |
N2—C2—N1 | 112.8 (2) | C2—N1—C8 | 106.5 (2) |
N2—C2—C10 | 123.4 (2) | C2—N1—C16 | 127.7 (2) |
N1—C2—C10 | 123.7 (2) | C8—N1—C16 | 125.1 (2) |
C5—C4—C9 | 117.4 (3) | C2—N2—C9 | 105.2 (2) |
C4—C5—C6 | 121.5 (3) | C17—N3—N4 | 113.0 (2) |
C7—C6—C5 | 122.0 (3) | C18—N4—N3 | 111.56 (19) |
C6—C7—C8 | 116.7 (3) | C18—N5—C19 | 127.5 (2) |
N1—C8—C7 | 132.3 (2) | C17—S1—C18 | 86.57 (12) |
N1—C8—C9 | 105.6 (2) | C5—C4—H4 | 121.3 |
C7—C8—C9 | 122.1 (3) | C9—C4—H4 | 121.3 |
C8—C9—N2 | 109.8 (2) | C4—C5—H5A | 119.3 |
C8—C9—C4 | 120.4 (2) | C6—C5—H5A | 119.3 |
N2—C9—C4 | 129.8 (3) | C7—C6—H6 | 119.1 |
C15—C10—C11 | 118.9 (2) | C5—C6—H6 | 119.1 |
C15—C10—C2 | 118.9 (2) | C6—C7—H7 | 121.6 |
C11—C10—C2 | 122.2 (2) | C8—C7—H7 | 121.6 |
C12—C11—C10 | 120.7 (3) | C12—C11—H11 | 119.6 |
C13—C12—C11 | 118.8 (3) | C10—C11—H11 | 119.6 |
C14—C13—C12 | 121.9 (3) | C13—C12—H12 | 120.6 |
C14—C13—Cl1 | 118.8 (2) | C11—C12—H12 | 120.6 |
C12—C13—Cl1 | 119.2 (2) | C13—C14—H14 | 120.5 |
C13—C14—C15 | 119.0 (3) | C15—C14—H14 | 120.5 |
C10—C15—C14 | 120.6 (3) | C10—C15—H15 | 119.7 |
N1—C16—C17 | 112.4 (2) | C14—C15—H15 | 119.7 |
N3—C17—C16 | 123.3 (2) | N1—C16—H16A | 109.1 |
N3—C17—S1 | 114.88 (19) | C17—C16—H16A | 109.1 |
C16—C17—S1 | 121.84 (17) | N1—C16—H16B | 109.1 |
N4—C18—N5 | 127.0 (2) | C17—C16—H16B | 109.1 |
N4—C18—S1 | 113.89 (19) | H16A—C16—H16B | 107.9 |
N5—C18—S1 | 119.08 (18) | C21—C20—H20 | 120.1 |
C24—C19—C20 | 117.0 (2) | C19—C20—H20 | 120.1 |
C24—C19—N5 | 117.3 (2) | C22—C21—H21 | 119.3 |
C20—C19—N5 | 125.7 (3) | C20—C21—H21 | 119.3 |
C21—C20—C19 | 119.8 (3) | C21—C22—H22 | 120.1 |
C22—C21—C20 | 121.3 (3) | C23—C22—H22 | 120.1 |
C23—C22—C21 | 119.8 (3) | C24—C23—H23 | 121.0 |
C24—C23—C22 | 118.1 (3) | C22—C23—H23 | 121.0 |
F1—C24—C23 | 118.4 (3) | C18—N5—H5 | 115.7 (16) |
F1—C24—C19 | 117.6 (2) | C19—N5—H5 | 116.3 (16) |
C23—C24—C19 | 124.0 (3) | | |
| | | |
C9—C4—C5—C6 | 0.7 (5) | C22—C23—C24—C19 | 1.3 (4) |
C4—C5—C6—C7 | −0.3 (5) | C20—C19—C24—F1 | 179.4 (2) |
C5—C6—C7—C8 | −1.3 (5) | N5—C19—C24—F1 | −0.6 (3) |
C6—C7—C8—N1 | −178.3 (3) | C20—C19—C24—C23 | −1.6 (4) |
C6—C7—C8—C9 | 2.6 (4) | N5—C19—C24—C23 | 178.4 (2) |
C7—C8—C9—N2 | 178.0 (2) | N2—C2—N1—C8 | −1.2 (3) |
N1—C8—C9—N2 | −1.4 (3) | C10—C2—N1—C8 | 177.5 (2) |
C7—C8—C9—C4 | −2.2 (4) | N2—C2—N1—C16 | −171.8 (2) |
N1—C8—C9—C4 | 178.4 (2) | C10—C2—N1—C16 | 6.9 (4) |
C5—C4—C9—C8 | 0.5 (4) | C7—C8—N1—C2 | −177.7 (3) |
C5—C4—C9—N2 | −179.8 (3) | C9—C8—N1—C2 | 1.5 (3) |
N2—C2—C10—C15 | 58.7 (3) | C7—C8—N1—C16 | −6.8 (4) |
N1—C2—C10—C15 | −119.9 (3) | C9—C8—N1—C16 | 172.4 (2) |
N2—C2—C10—C11 | −120.6 (3) | C17—C16—N1—C2 | 92.9 (3) |
N1—C2—C10—C11 | 60.9 (3) | C17—C16—N1—C8 | −76.1 (3) |
C15—C10—C11—C12 | 0.4 (4) | N1—C2—N2—C9 | 0.4 (3) |
C2—C10—C11—C12 | 179.7 (2) | C10—C2—N2—C9 | −178.3 (2) |
C10—C11—C12—C13 | 1.7 (4) | C8—C9—N2—C2 | 0.6 (3) |
C11—C12—C13—C14 | −2.6 (4) | C4—C9—N2—C2 | −179.1 (3) |
C11—C12—C13—Cl1 | 174.1 (2) | C16—C17—N3—N4 | −179.7 (2) |
C12—C13—C14—C15 | 1.3 (4) | S1—C17—N3—N4 | 0.3 (3) |
Cl1—C13—C14—C15 | −175.4 (2) | N5—C18—N4—N3 | 178.3 (2) |
C11—C10—C15—C14 | −1.7 (4) | S1—C18—N4—N3 | −2.5 (3) |
C2—C10—C15—C14 | 179.0 (3) | C17—N3—N4—C18 | 1.4 (3) |
C13—C14—C15—C10 | 0.9 (4) | N4—C18—N5—C19 | −4.7 (4) |
N1—C16—C17—N3 | 127.3 (2) | S1—C18—N5—C19 | 176.1 (2) |
N1—C16—C17—S1 | −52.7 (3) | C24—C19—N5—C18 | −177.7 (2) |
C24—C19—C20—C21 | 0.6 (4) | C20—C19—N5—C18 | 2.2 (4) |
N5—C19—C20—C21 | −179.3 (2) | N3—C17—S1—C18 | −1.4 (2) |
C19—C20—C21—C22 | 0.5 (5) | C16—C17—S1—C18 | 178.6 (2) |
C20—C21—C22—C23 | −0.8 (5) | N4—C18—S1—C17 | 2.21 (19) |
C21—C22—C23—C24 | −0.1 (5) | N5—C18—S1—C17 | −178.6 (2) |
C22—C23—C24—F1 | −179.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···F1 | 0.87 (2) | 2.27 (2) | 2.654 (3) | 106.3 (18) |
C20—H20···N4 | 0.93 | 2.34 | 2.948 (4) | 123 |
N5—H5···N2i | 0.87 (2) | 2.08 (2) | 2.921 (3) | 161.3 |
C6—H6···Cg(1)ii | 0.93 | 3.14 | 3.940 (5) | 145 |
C11—H11···Cg(2)iii | 0.93 | 3.00 | 3.806 (3) | 146 |
C12—H12···Cg(3)iii | 0.93 | 2.92 | 3.676 (3) | 140 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1; (iii) −x+1/2, y+1/2, −z+1/2. |