Download citation
Download citation
link to html
In the title compound, C22H15ClFN5S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021265/kj2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021265/kj2045Isup2.hkl
Contains datablock I

CCDC reference: 651376

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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).

(I) top
Crystal data top
C22H15ClFN5SF(000) = 1792
Mr = 435.9Dx = 1.423 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 25.583 (5) Åθ = 9.9–18.1°
b = 9.9377 (14) ŵ = 0.32 mm1
c = 20.207 (3) ÅT = 293 K
β = 127.599 (12)°Prism, colourless
V = 4070.3 (12) Å30.36 × 0.33 × 0.24 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.043
ω/2θ scansθmax = 26.3°, θmin = 2.3°
Absorption correction: ψ scan
(North et al., 1968)
h = 310
Tmin = 0.894, Tmax = 0.927k = 120
4033 measured reflectionsl = 1925
3948 independent reflections3 standard reflections every 120 min
2473 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH 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 = 1.03Δρmax = 0.21 e Å3
3948 reflectionsΔρmin = 0.29 e Å3
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
xyzUiso*/Ueq
C20.73303 (12)0.1194 (2)0.74358 (15)0.0387 (6)
C40.60582 (14)0.1607 (3)0.76226 (19)0.0565 (8)
H40.56520.17850.71140.068*
C50.61246 (16)0.1521 (3)0.8349 (2)0.0648 (9)
H5A0.57550.16320.83290.078*
C60.67349 (17)0.1272 (3)0.9115 (2)0.0650 (9)
H60.67610.12260.95940.078*
C70.72965 (15)0.1093 (3)0.91821 (17)0.0542 (7)
H70.77040.09440.96950.065*
C80.72274 (12)0.1146 (2)0.84460 (16)0.0406 (6)
C90.66244 (12)0.1418 (3)0.76784 (15)0.0421 (6)
C100.76349 (12)0.1167 (2)0.70061 (15)0.0393 (6)
C110.79438 (13)0.0027 (3)0.69954 (16)0.0472 (7)
H110.79640.07490.72680.057*
C120.82210 (13)0.0034 (3)0.65850 (17)0.0531 (7)
H120.84170.07370.65660.064*
C130.82016 (13)0.1196 (3)0.62069 (16)0.0503 (7)
C140.78944 (15)0.2329 (3)0.61965 (18)0.0614 (8)
H140.78790.31020.59260.074*
C150.76056 (14)0.2310 (3)0.65947 (17)0.0534 (7)
H150.7390.30720.65850.064*
C160.83863 (12)0.0835 (3)0.89070 (15)0.0415 (6)
H16A0.85710.04660.86460.050*
H16B0.84740.02030.9330.050*
C170.87199 (11)0.2149 (2)0.93180 (14)0.0363 (6)
C180.91232 (11)0.4387 (3)0.97000 (14)0.0357 (6)
C190.96178 (12)0.6568 (3)1.03957 (15)0.0396 (6)
C200.99454 (13)0.6191 (3)1.12250 (16)0.0523 (7)
H200.99340.53011.13570.063*
C211.02871 (15)0.7142 (4)1.18505 (18)0.0630 (9)
H211.05070.68811.24030.076*
C221.03085 (15)0.8469 (4)1.1672 (2)0.0662 (9)
H221.05370.90981.21010.079*
C230.99901 (14)0.8862 (3)1.08553 (19)0.0572 (8)
H230.99990.97541.07230.069*
C240.96614 (12)0.7904 (3)1.02453 (16)0.0452 (7)
Cl10.86142 (4)0.12627 (11)0.57715 (5)0.0822 (3)
F10.93480 (8)0.82834 (16)0.94364 (10)0.0615 (5)
N10.76745 (10)0.0981 (2)0.82778 (12)0.0382 (5)
N20.67032 (10)0.1453 (2)0.70541 (12)0.0440 (5)
N30.91089 (11)0.2316 (2)1.01154 (13)0.0468 (6)
N40.93564 (11)0.3616 (2)1.03505 (12)0.0463 (6)
N50.92497 (10)0.5713 (2)0.97037 (13)0.0417 (5)
S10.86067 (3)0.35519 (7)0.87464 (4)0.0449 (2)
H50.9030 (12)0.609 (2)0.9211 (15)0.043 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0433 (15)0.0292 (14)0.0404 (13)0.0032 (11)0.0240 (12)0.0051 (11)
C40.0458 (16)0.0549 (19)0.0637 (18)0.0070 (14)0.0307 (15)0.0166 (15)
C50.064 (2)0.071 (2)0.080 (2)0.0102 (17)0.0545 (19)0.0149 (18)
C60.081 (2)0.069 (2)0.070 (2)0.0092 (18)0.058 (2)0.0048 (17)
C70.0640 (19)0.0527 (19)0.0510 (17)0.0032 (15)0.0378 (15)0.0000 (14)
C80.0458 (15)0.0307 (14)0.0475 (15)0.0071 (11)0.0296 (13)0.0069 (11)
C90.0440 (14)0.0359 (14)0.0450 (14)0.0052 (12)0.0265 (13)0.0111 (12)
C100.0417 (14)0.0335 (15)0.0372 (13)0.0021 (11)0.0213 (12)0.0053 (11)
C110.0520 (16)0.0367 (15)0.0519 (16)0.0020 (12)0.0312 (14)0.0034 (12)
C120.0519 (17)0.0508 (18)0.0586 (17)0.0032 (14)0.0348 (15)0.0132 (15)
C130.0479 (16)0.063 (2)0.0428 (15)0.0109 (15)0.0288 (13)0.0131 (14)
C140.080 (2)0.055 (2)0.0577 (18)0.0034 (17)0.0463 (17)0.0097 (15)
C150.0682 (19)0.0432 (16)0.0547 (17)0.0116 (15)0.0405 (16)0.0070 (14)
C160.0399 (14)0.0336 (14)0.0448 (14)0.0034 (12)0.0227 (12)0.0029 (12)
C170.0351 (13)0.0329 (14)0.0378 (13)0.0044 (11)0.0206 (11)0.0049 (11)
C180.0289 (12)0.0418 (15)0.0342 (13)0.0004 (11)0.0181 (11)0.0003 (11)
C190.0331 (13)0.0436 (16)0.0420 (14)0.0032 (12)0.0228 (11)0.0030 (12)
C200.0491 (16)0.0551 (19)0.0427 (15)0.0067 (14)0.0229 (13)0.0022 (14)
C210.0560 (18)0.077 (2)0.0437 (16)0.0158 (17)0.0243 (15)0.0141 (16)
C220.0524 (18)0.072 (2)0.064 (2)0.0222 (17)0.0302 (16)0.0270 (18)
C230.0491 (17)0.0473 (18)0.071 (2)0.0124 (14)0.0349 (16)0.0125 (15)
C240.0351 (13)0.0480 (17)0.0470 (15)0.0031 (13)0.0221 (12)0.0027 (13)
Cl10.0785 (6)0.1167 (8)0.0773 (6)0.0246 (5)0.0608 (5)0.0249 (5)
F10.0681 (11)0.0432 (10)0.0561 (10)0.0034 (8)0.0290 (9)0.0065 (8)
N10.0386 (11)0.0337 (12)0.0381 (11)0.0005 (9)0.0213 (10)0.0006 (9)
N20.0396 (12)0.0441 (13)0.0408 (12)0.0013 (10)0.0207 (10)0.0103 (10)
N30.0533 (13)0.0401 (13)0.0411 (13)0.0051 (11)0.0257 (11)0.0025 (10)
N40.0547 (14)0.0420 (13)0.0338 (11)0.0076 (11)0.0226 (10)0.0019 (10)
N50.0445 (13)0.0352 (13)0.0336 (12)0.0040 (10)0.0177 (10)0.0032 (10)
S10.0481 (4)0.0379 (4)0.0332 (3)0.0028 (3)0.0169 (3)0.0022 (3)
Geometric parameters (Å, º) top
C2—N21.313 (3)C19—C241.381 (4)
C2—N11.374 (3)C19—C201.392 (3)
C2—C101.479 (4)C19—N51.399 (3)
C4—C51.373 (4)C20—C211.381 (4)
C4—C91.395 (4)C21—C221.378 (4)
C5—C61.395 (4)C22—C231.378 (4)
C6—C71.370 (4)C23—C241.367 (4)
C7—C81.387 (4)C24—F11.363 (3)
C8—N11.388 (3)N3—N41.389 (3)
C8—C91.393 (3)N5—H50.87 (2)
C9—N21.394 (3)C4—H40.9300
C10—C151.382 (4)C5—H5A0.9300
C10—C111.389 (3)C6—H60.9300
C11—C121.381 (4)C7—H70.9300
C12—C131.369 (4)C11—H110.9300
C13—C141.366 (4)C12—H120.9300
C13—Cl11.740 (3)C14—H140.9300
C14—C151.385 (4)C15—H150.9300
C16—N11.459 (3)C16—H16A0.9700
C16—C171.503 (3)C16—H16B0.9700
C17—N31.288 (3)C20—H200.9300
C17—S11.719 (2)C21—H210.9300
C18—N41.309 (3)C22—H220.9300
C18—N51.356 (3)C23—H230.9300
C18—S11.744 (2)
N2—C2—N1112.8 (2)C2—N1—C8106.5 (2)
N2—C2—C10123.4 (2)C2—N1—C16127.7 (2)
N1—C2—C10123.7 (2)C8—N1—C16125.1 (2)
C5—C4—C9117.4 (3)C2—N2—C9105.2 (2)
C4—C5—C6121.5 (3)C17—N3—N4113.0 (2)
C7—C6—C5122.0 (3)C18—N4—N3111.56 (19)
C6—C7—C8116.7 (3)C18—N5—C19127.5 (2)
N1—C8—C7132.3 (2)C17—S1—C1886.57 (12)
N1—C8—C9105.6 (2)C5—C4—H4121.3
C7—C8—C9122.1 (3)C9—C4—H4121.3
C8—C9—N2109.8 (2)C4—C5—H5A119.3
C8—C9—C4120.4 (2)C6—C5—H5A119.3
N2—C9—C4129.8 (3)C7—C6—H6119.1
C15—C10—C11118.9 (2)C5—C6—H6119.1
C15—C10—C2118.9 (2)C6—C7—H7121.6
C11—C10—C2122.2 (2)C8—C7—H7121.6
C12—C11—C10120.7 (3)C12—C11—H11119.6
C13—C12—C11118.8 (3)C10—C11—H11119.6
C14—C13—C12121.9 (3)C13—C12—H12120.6
C14—C13—Cl1118.8 (2)C11—C12—H12120.6
C12—C13—Cl1119.2 (2)C13—C14—H14120.5
C13—C14—C15119.0 (3)C15—C14—H14120.5
C10—C15—C14120.6 (3)C10—C15—H15119.7
N1—C16—C17112.4 (2)C14—C15—H15119.7
N3—C17—C16123.3 (2)N1—C16—H16A109.1
N3—C17—S1114.88 (19)C17—C16—H16A109.1
C16—C17—S1121.84 (17)N1—C16—H16B109.1
N4—C18—N5127.0 (2)C17—C16—H16B109.1
N4—C18—S1113.89 (19)H16A—C16—H16B107.9
N5—C18—S1119.08 (18)C21—C20—H20120.1
C24—C19—C20117.0 (2)C19—C20—H20120.1
C24—C19—N5117.3 (2)C22—C21—H21119.3
C20—C19—N5125.7 (3)C20—C21—H21119.3
C21—C20—C19119.8 (3)C21—C22—H22120.1
C22—C21—C20121.3 (3)C23—C22—H22120.1
C23—C22—C21119.8 (3)C24—C23—H23121.0
C24—C23—C22118.1 (3)C22—C23—H23121.0
F1—C24—C23118.4 (3)C18—N5—H5115.7 (16)
F1—C24—C19117.6 (2)C19—N5—H5116.3 (16)
C23—C24—C19124.0 (3)
C9—C4—C5—C60.7 (5)C22—C23—C24—C191.3 (4)
C4—C5—C6—C70.3 (5)C20—C19—C24—F1179.4 (2)
C5—C6—C7—C81.3 (5)N5—C19—C24—F10.6 (3)
C6—C7—C8—N1178.3 (3)C20—C19—C24—C231.6 (4)
C6—C7—C8—C92.6 (4)N5—C19—C24—C23178.4 (2)
C7—C8—C9—N2178.0 (2)N2—C2—N1—C81.2 (3)
N1—C8—C9—N21.4 (3)C10—C2—N1—C8177.5 (2)
C7—C8—C9—C42.2 (4)N2—C2—N1—C16171.8 (2)
N1—C8—C9—C4178.4 (2)C10—C2—N1—C166.9 (4)
C5—C4—C9—C80.5 (4)C7—C8—N1—C2177.7 (3)
C5—C4—C9—N2179.8 (3)C9—C8—N1—C21.5 (3)
N2—C2—C10—C1558.7 (3)C7—C8—N1—C166.8 (4)
N1—C2—C10—C15119.9 (3)C9—C8—N1—C16172.4 (2)
N2—C2—C10—C11120.6 (3)C17—C16—N1—C292.9 (3)
N1—C2—C10—C1160.9 (3)C17—C16—N1—C876.1 (3)
C15—C10—C11—C120.4 (4)N1—C2—N2—C90.4 (3)
C2—C10—C11—C12179.7 (2)C10—C2—N2—C9178.3 (2)
C10—C11—C12—C131.7 (4)C8—C9—N2—C20.6 (3)
C11—C12—C13—C142.6 (4)C4—C9—N2—C2179.1 (3)
C11—C12—C13—Cl1174.1 (2)C16—C17—N3—N4179.7 (2)
C12—C13—C14—C151.3 (4)S1—C17—N3—N40.3 (3)
Cl1—C13—C14—C15175.4 (2)N5—C18—N4—N3178.3 (2)
C11—C10—C15—C141.7 (4)S1—C18—N4—N32.5 (3)
C2—C10—C15—C14179.0 (3)C17—N3—N4—C181.4 (3)
C13—C14—C15—C100.9 (4)N4—C18—N5—C194.7 (4)
N1—C16—C17—N3127.3 (2)S1—C18—N5—C19176.1 (2)
N1—C16—C17—S152.7 (3)C24—C19—N5—C18177.7 (2)
C24—C19—C20—C210.6 (4)C20—C19—N5—C182.2 (4)
N5—C19—C20—C21179.3 (2)N3—C17—S1—C181.4 (2)
C19—C20—C21—C220.5 (5)C16—C17—S1—C18178.6 (2)
C20—C21—C22—C230.8 (5)N4—C18—S1—C172.21 (19)
C21—C22—C23—C240.1 (5)N5—C18—S1—C17178.6 (2)
C22—C23—C24—F1179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5···F10.87 (2)2.27 (2)2.654 (3)106.3 (18)
C20—H20···N40.932.342.948 (4)123
N5—H5···N2i0.87 (2)2.08 (2)2.921 (3)161.3
C6—H6···Cg(1)ii0.933.143.940 (5)145
C11—H11···Cg(2)iii0.933.003.806 (3)146
C12—H12···Cg(3)iii0.932.923.676 (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.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds