organic compounds
3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, bDepartment of Chemistry, Faculty of Science, Mansoura University, ET-35516 Mansoura, Egypt, cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound, C16H13ClFN3S, the pyrazole ring adopts an with the methine C atom being the flap atom. The chloro- and fluorobenzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intramolecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supramolecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.
Related literature
For the biological activity of pyrazolin-1-ylthiazoles, see: Abdel-Wahab et al. (2009, 2012); Chimenti et al. (2010). For related structures, see: Chantrapromma et al. (2012); Abdel-Wahab et al. (2013).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536813004492/hg5293sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004492/hg5293Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004492/hg5293Isup3.cml
To a suspension of (E)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (1 mmol, 0.26 g) and sodium hydroxide (2.5 mmol, 1.0 g) in ethanol (20 ml), thiosemicarbazide (1.2 mmol, 0.11 g) was added. The mixture was refluxed for 12 h, then left to cool. The solid product was filtered off, washed with ethanol and dried. Recrystallization was by slow evaporation of its DMF solution.
Nitrogen- and carbon-bound H-atoms were placed in calculated positions (N—H = 0.88 Å, and C—H 0.93 to 0.98 Å) and were included in the
in the riding model approximation, with Uiso(H) = 1.2–1.5Uequiv(N,C).Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).C16H13ClFN3S | F(000) = 688 |
Mr = 333.80 | Dx = 1.464 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2717 reflections |
a = 14.5402 (9) Å | θ = 2.9–27.5° |
b = 11.2700 (8) Å | µ = 0.40 mm−1 |
c = 9.5169 (6) Å | T = 295 K |
β = 103.850 (6)° | Prism, colourless |
V = 1514.17 (17) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Agilent SuperNova Dual diffractometer with an Atlas detector | 3478 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2570 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.031 |
Detector resolution: 10.4041 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω scan | h = −15→18 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −14→11 |
Tmin = 0.898, Tmax = 1.000 | l = −12→12 |
10191 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0432P)2 + 0.4541P] where P = (Fo2 + 2Fc2)/3 |
3478 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C16H13ClFN3S | V = 1514.17 (17) Å3 |
Mr = 333.80 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.5402 (9) Å | µ = 0.40 mm−1 |
b = 11.2700 (8) Å | T = 295 K |
c = 9.5169 (6) Å | 0.40 × 0.30 × 0.20 mm |
β = 103.850 (6)° |
Agilent SuperNova Dual diffractometer with an Atlas detector | 3478 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 2570 reflections with I > 2σ(I) |
Tmin = 0.898, Tmax = 1.000 | Rint = 0.031 |
10191 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.19 e Å−3 |
3478 reflections | Δρmin = −0.28 e Å−3 |
199 parameters |
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 | ||
Cl1 | 0.54931 (5) | 0.65490 (7) | 0.48095 (8) | 0.0811 (3) | |
S1 | −0.01110 (4) | 1.16708 (5) | −0.15948 (5) | 0.04527 (17) | |
F1 | 0.27125 (11) | 1.14248 (13) | −0.60633 (13) | 0.0658 (4) | |
N1 | 0.20984 (11) | 1.00001 (15) | 0.08010 (15) | 0.0379 (4) | |
N2 | 0.13525 (11) | 1.03202 (14) | −0.03592 (15) | 0.0368 (4) | |
N3 | 0.10065 (13) | 1.17944 (16) | 0.10514 (17) | 0.0463 (4) | |
H31 | 0.1483 | 1.1542 | 0.1741 | 0.056* | |
H32 | 0.0669 | 1.2407 | 0.1207 | 0.056* | |
C1 | 0.31834 (13) | 0.83907 (18) | 0.1544 (2) | 0.0381 (4) | |
C2 | 0.37595 (15) | 0.9020 (2) | 0.2678 (2) | 0.0498 (5) | |
H2 | 0.3661 | 0.9829 | 0.2772 | 0.060* | |
C3 | 0.44754 (16) | 0.8454 (2) | 0.3665 (2) | 0.0559 (6) | |
H3 | 0.4860 | 0.8879 | 0.4419 | 0.067* | |
C4 | 0.46163 (14) | 0.7261 (2) | 0.3529 (2) | 0.0505 (6) | |
C5 | 0.40755 (15) | 0.6624 (2) | 0.2408 (3) | 0.0533 (6) | |
H5 | 0.4187 | 0.5819 | 0.2314 | 0.064* | |
C6 | 0.33602 (14) | 0.7194 (2) | 0.1414 (2) | 0.0476 (5) | |
H6 | 0.2993 | 0.6766 | 0.0647 | 0.057* | |
C7 | 0.23925 (13) | 0.89711 (18) | 0.05223 (19) | 0.0366 (4) | |
C8 | 0.18302 (14) | 0.84371 (17) | −0.08689 (19) | 0.0394 (4) | |
H8A | 0.1424 | 0.7802 | −0.0687 | 0.047* | |
H8B | 0.2242 | 0.8136 | −0.1452 | 0.047* | |
C9 | 0.12464 (13) | 0.95057 (17) | −0.15998 (18) | 0.0365 (4) | |
H9 | 0.0581 | 0.9282 | −0.1966 | 0.044* | |
C10 | 0.16342 (12) | 1.00448 (17) | −0.27969 (17) | 0.0330 (4) | |
C11 | 0.23938 (13) | 1.08168 (18) | −0.24895 (19) | 0.0403 (5) | |
H11 | 0.2656 | 1.1032 | −0.1534 | 0.048* | |
C12 | 0.27723 (14) | 1.12774 (19) | −0.3580 (2) | 0.0442 (5) | |
H12 | 0.3288 | 1.1791 | −0.3370 | 0.053* | |
C13 | 0.23618 (15) | 1.09503 (19) | −0.4978 (2) | 0.0430 (5) | |
C14 | 0.16111 (15) | 1.01890 (19) | −0.53370 (19) | 0.0463 (5) | |
H14 | 0.1350 | 0.9983 | −0.6296 | 0.056* | |
C15 | 0.12497 (14) | 0.97331 (18) | −0.42252 (19) | 0.0400 (4) | |
H15 | 0.0741 | 0.9210 | −0.4442 | 0.048* | |
C16 | 0.07946 (13) | 1.12480 (17) | −0.02300 (19) | 0.0352 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0556 (4) | 0.0764 (5) | 0.0967 (5) | 0.0061 (3) | −0.0106 (3) | 0.0318 (4) |
S1 | 0.0410 (3) | 0.0485 (4) | 0.0446 (3) | 0.0047 (2) | 0.0067 (2) | 0.0045 (2) |
F1 | 0.0922 (10) | 0.0679 (10) | 0.0444 (7) | −0.0139 (8) | 0.0304 (7) | 0.0066 (6) |
N1 | 0.0384 (8) | 0.0440 (10) | 0.0306 (7) | 0.0025 (7) | 0.0068 (6) | 0.0007 (7) |
N2 | 0.0406 (8) | 0.0402 (10) | 0.0295 (7) | 0.0046 (7) | 0.0080 (6) | −0.0024 (6) |
N3 | 0.0537 (10) | 0.0438 (10) | 0.0409 (9) | 0.0073 (8) | 0.0106 (7) | −0.0069 (7) |
C1 | 0.0368 (10) | 0.0409 (12) | 0.0380 (9) | 0.0007 (8) | 0.0116 (7) | 0.0033 (8) |
C2 | 0.0544 (13) | 0.0427 (13) | 0.0485 (12) | 0.0034 (10) | 0.0045 (9) | −0.0004 (9) |
C3 | 0.0520 (13) | 0.0587 (16) | 0.0488 (12) | −0.0014 (11) | −0.0041 (10) | 0.0004 (10) |
C4 | 0.0349 (10) | 0.0542 (15) | 0.0606 (13) | 0.0006 (10) | 0.0078 (9) | 0.0182 (11) |
C5 | 0.0412 (11) | 0.0397 (13) | 0.0768 (15) | 0.0024 (10) | 0.0094 (10) | 0.0066 (11) |
C6 | 0.0400 (11) | 0.0449 (13) | 0.0565 (12) | −0.0026 (9) | 0.0091 (9) | −0.0029 (10) |
C7 | 0.0360 (10) | 0.0397 (12) | 0.0361 (9) | −0.0015 (8) | 0.0129 (7) | 0.0007 (8) |
C8 | 0.0462 (11) | 0.0372 (11) | 0.0355 (9) | −0.0004 (9) | 0.0111 (8) | −0.0002 (8) |
C9 | 0.0364 (9) | 0.0401 (11) | 0.0324 (9) | −0.0022 (8) | 0.0074 (7) | −0.0048 (8) |
C10 | 0.0329 (9) | 0.0343 (10) | 0.0307 (8) | 0.0027 (8) | 0.0056 (7) | −0.0015 (7) |
C11 | 0.0412 (10) | 0.0458 (12) | 0.0313 (9) | −0.0044 (9) | 0.0033 (7) | −0.0028 (8) |
C12 | 0.0431 (11) | 0.0462 (13) | 0.0437 (11) | −0.0074 (9) | 0.0114 (8) | −0.0010 (9) |
C13 | 0.0575 (12) | 0.0397 (12) | 0.0354 (10) | 0.0030 (10) | 0.0181 (9) | 0.0038 (8) |
C14 | 0.0605 (13) | 0.0466 (13) | 0.0289 (9) | −0.0014 (10) | 0.0053 (8) | −0.0020 (8) |
C15 | 0.0440 (11) | 0.0380 (11) | 0.0350 (9) | −0.0046 (9) | 0.0037 (8) | −0.0030 (8) |
C16 | 0.0378 (9) | 0.0351 (11) | 0.0358 (9) | −0.0042 (8) | 0.0148 (7) | 0.0024 (8) |
Cl1—C4 | 1.735 (2) | C5—H5 | 0.9300 |
S1—C16 | 1.6821 (19) | C6—H6 | 0.9300 |
F1—C13 | 1.365 (2) | C7—C8 | 1.505 (2) |
N1—C7 | 1.285 (2) | C8—C9 | 1.540 (3) |
N1—N2 | 1.397 (2) | C8—H8A | 0.9700 |
N2—C16 | 1.347 (2) | C8—H8B | 0.9700 |
N2—C9 | 1.474 (2) | C9—C10 | 1.514 (3) |
N3—C16 | 1.335 (2) | C9—H9 | 0.9800 |
N3—H31 | 0.8800 | C10—C11 | 1.381 (3) |
N3—H32 | 0.8800 | C10—C15 | 1.386 (2) |
C1—C6 | 1.384 (3) | C11—C12 | 1.386 (3) |
C1—C2 | 1.392 (3) | C11—H11 | 0.9300 |
C1—C7 | 1.470 (3) | C12—C13 | 1.373 (3) |
C2—C3 | 1.380 (3) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.366 (3) |
C3—C4 | 1.371 (3) | C14—C15 | 1.388 (3) |
C3—H3 | 0.9300 | C14—H14 | 0.9300 |
C4—C5 | 1.367 (3) | C15—H15 | 0.9300 |
C5—C6 | 1.385 (3) | ||
C7—N1—N2 | 107.67 (15) | C7—C8—H8B | 111.4 |
C16—N2—N1 | 119.92 (15) | C9—C8—H8B | 111.4 |
C16—N2—C9 | 127.35 (15) | H8A—C8—H8B | 109.2 |
N1—N2—C9 | 112.63 (14) | N2—C9—C10 | 111.49 (15) |
C16—N3—H31 | 120.0 | N2—C9—C8 | 100.63 (13) |
C16—N3—H32 | 120.0 | C10—C9—C8 | 112.91 (15) |
H31—N3—H32 | 120.0 | N2—C9—H9 | 110.5 |
C6—C1—C2 | 118.41 (18) | C10—C9—H9 | 110.5 |
C6—C1—C7 | 120.48 (18) | C8—C9—H9 | 110.5 |
C2—C1—C7 | 121.10 (19) | C11—C10—C15 | 118.82 (17) |
C3—C2—C1 | 120.5 (2) | C11—C10—C9 | 121.08 (15) |
C3—C2—H2 | 119.7 | C15—C10—C9 | 120.06 (17) |
C1—C2—H2 | 119.7 | C10—C11—C12 | 121.19 (17) |
C4—C3—C2 | 119.7 (2) | C10—C11—H11 | 119.4 |
C4—C3—H3 | 120.2 | C12—C11—H11 | 119.4 |
C2—C3—H3 | 120.2 | C13—C12—C11 | 117.83 (19) |
C3—C4—C5 | 121.16 (19) | C13—C12—H12 | 121.1 |
C3—C4—Cl1 | 119.23 (17) | C11—C12—H12 | 121.1 |
C5—C4—Cl1 | 119.61 (19) | C14—C13—F1 | 118.55 (17) |
C4—C5—C6 | 119.1 (2) | C14—C13—C12 | 123.16 (18) |
C4—C5—H5 | 120.4 | F1—C13—C12 | 118.28 (19) |
C6—C5—H5 | 120.4 | C13—C14—C15 | 117.89 (17) |
C5—C6—C1 | 121.1 (2) | C13—C14—H14 | 121.1 |
C5—C6—H6 | 119.5 | C15—C14—H14 | 121.1 |
C1—C6—H6 | 119.5 | C10—C15—C14 | 121.10 (18) |
N1—C7—C1 | 120.74 (17) | C10—C15—H15 | 119.4 |
N1—C7—C8 | 113.88 (16) | C14—C15—H15 | 119.4 |
C1—C7—C8 | 125.33 (18) | N3—C16—N2 | 115.42 (16) |
C7—C8—C9 | 102.08 (15) | N3—C16—S1 | 122.79 (16) |
C7—C8—H8A | 111.4 | N2—C16—S1 | 121.78 (14) |
C9—C8—H8A | 111.4 | ||
C7—N1—N2—C16 | 167.15 (16) | C16—N2—C9—C8 | −159.69 (18) |
C7—N1—N2—C9 | −9.4 (2) | N1—N2—C9—C8 | 16.59 (19) |
C6—C1—C2—C3 | −1.4 (3) | C7—C8—C9—N2 | −16.22 (18) |
C7—C1—C2—C3 | 177.32 (19) | C7—C8—C9—C10 | 102.72 (17) |
C1—C2—C3—C4 | −0.3 (3) | N2—C9—C10—C11 | 31.9 (2) |
C2—C3—C4—C5 | 1.8 (4) | C8—C9—C10—C11 | −80.5 (2) |
C2—C3—C4—Cl1 | −177.91 (17) | N2—C9—C10—C15 | −150.42 (17) |
C3—C4—C5—C6 | −1.4 (4) | C8—C9—C10—C15 | 97.1 (2) |
Cl1—C4—C5—C6 | 178.23 (17) | C15—C10—C11—C12 | −0.1 (3) |
C4—C5—C6—C1 | −0.3 (3) | C9—C10—C11—C12 | 177.60 (18) |
C2—C1—C6—C5 | 1.7 (3) | C10—C11—C12—C13 | 0.6 (3) |
C7—C1—C6—C5 | −177.00 (19) | C11—C12—C13—C14 | −0.7 (3) |
N2—N1—C7—C1 | 179.67 (16) | C11—C12—C13—F1 | 178.21 (18) |
N2—N1—C7—C8 | −2.9 (2) | F1—C13—C14—C15 | −178.68 (19) |
C6—C1—C7—N1 | 165.27 (18) | C12—C13—C14—C15 | 0.2 (3) |
C2—C1—C7—N1 | −13.4 (3) | C11—C10—C15—C14 | −0.4 (3) |
C6—C1—C7—C8 | −11.9 (3) | C9—C10—C15—C14 | −178.12 (18) |
C2—C1—C7—C8 | 169.41 (19) | C13—C14—C15—C10 | 0.3 (3) |
N1—C7—C8—C9 | 12.9 (2) | N1—N2—C16—N3 | −0.7 (2) |
C1—C7—C8—C9 | −169.76 (17) | C9—N2—C16—N3 | 175.38 (17) |
C16—N2—C9—C10 | 80.3 (2) | N1—N2—C16—S1 | 179.89 (13) |
N1—N2—C9—C10 | −103.38 (17) | C9—N2—C16—S1 | −4.1 (3) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H31···N1 | 0.88 | 2.24 | 2.617 (2) | 106 |
N3—H31···F1i | 0.88 | 2.41 | 3.257 (2) | 163 |
N3—H32···S1ii | 0.88 | 2.81 | 3.5203 (19) | 139 |
C4—Cl1···Cg1iii | 1.74 (1) | 3.92 (1) | 4.183 (2) | 86 (1) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+5/2, z+1/2; (iii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClFN3S |
Mr | 333.80 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 14.5402 (9), 11.2700 (8), 9.5169 (6) |
β (°) | 103.850 (6) |
V (Å3) | 1514.17 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Agilent SuperNova Dual diffractometer with an Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.898, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10191, 3478, 2570 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.111, 1.01 |
No. of reflections | 3478 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.28 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H31···N1 | 0.88 | 2.24 | 2.617 (2) | 106 |
N3—H31···F1i | 0.88 | 2.41 | 3.257 (2) | 163 |
N3—H32···S1ii | 0.88 | 2.81 | 3.5203 (19) | 139 |
C4—Cl1···Cg1iii | 1.735 (2) | 3.9240 (12) | 4.183 (2) | 86.17 (7) |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+5/2, z+1/2; (iii) x, −y+1/2, z−1/2. |
Footnotes
‡Additional correspondence author, e-mail: bakrfatehy@yahoo.com.
Acknowledgements
We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).
References
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Pyrazolin-1-ylthiazole derivatives are known to exhibit biological potential (Abdel-Wahab et al., 2012; Abdel-Wahab et al., 2009; Chimenti et al., 2010) and motivated the investigation of the title compound, (I).
The central pyrazolyl ring in (I), Fig. 1, adopts an envelope conformation with the methine-C9 atom being the flap atom. The amine group is orientated towards the ring-N2 atom, forming a hydrogen bond, Table 1, assisted by the near co-planar relationship between the thioamide group and the pyrazolyl ring with the N1—N2—C16—N3 torsion angle being -0.7 (2)°. Both the chloro- and fluoro-benzene rings are twisted out of the least-squares plane through the five-membered ring, forming dihedral angles of 15.12 (11) and 80.55 (10)°, respectively. Quite similar conformations have been observed in related structures bearing two six-membered rings (Chantrapromma et al., 2012; Abdel-Wahab et al., 2013).
In the crystal packing, the amine-H31 atom participating in the intramolecular N—H···N hydrogen bond also forms a hydrogen bond to the F1 atom, Table 1. This interaction along with an N—H···S hydrogen bond leads to a supramolecular chain along the c axis, Table 1. Chains are connected into a layer in the bc plane by Cl···π interactions, Fig. 2 and Table 1. Layers stack along the a axis without specific interactions between them, Fig. 3.