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The title compound, (1S,3R,8R)-2,2-dichloro-3,7,7,10-tetra­methyl­tricyclo­[6.4.0.01,3]­dodecan-11-one thio­semicarbazone, C17H25Cl2N3S, has two disordered conformations of the cyclo­heptane moiety and a screw-boat conformation for the cyclo­hexene ring. The absolute configuration was established.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105033470/ln1186sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105033470/ln1186Isup2.hkl
Contains datablock I

CCDC reference: 294330

Comment top

Thiosemicarbazone compounds exhibit well known pharmacological activities, such as selective inhibition of the herpes virus (Blumenkopf et al., 1992) or inhibition of human immunodeficiency virus (HIV) (Teitz et al., 1994). Within the framework of the evaluation of Moroccan natural resources, we have undertaken the synthesis and characterization of such compounds. The dichlorocyclopropanation (Auhmani et al., 2002; Eljamili et al., 2002) of β-himachalene (Plattier & Teisseire, 1974), a major sesquiterpene isolated from the essential oil of Atlantical Cedrus, followed by oxidation using N-bromosuccinimide and condensation with thiosemicarbazide, led to the title compound, (I). The structure of (I) was elucidated by 1H and 13C NMR spectroscopies and its absolute configuration established by single-crystal X-ray diffraction analysis.

The overall shape of the molecule of (I) can be described as two domains, with a globular hydrophobic core consisting of three substituted fused rings and an elongated hydrophilic thiosemicarbazone tail (Fig. 1). The absolute configuration of (I) was established without ambiguity from the anomalous dispersion of the S and Cl atoms and confirmed that the stereochemistry of the ring junction atoms as C1(S), C3(R) and C8(R) (Fig. 1). The cyclohexene ring is distorted and the puckering parameters (Cremer & Pople, 1975) show that its conformation is close to that of a screw-boat: the θ and ϕ angles calculated for the atom sequence C8/C9/C10/C11/C12/C1 are 67.7 (2) and 324.4 (3)°, respectively. The thiosemicarbazone substituent on the cyclohexene ring adopts a planar zigzag conformation, with the N—H bond cis to the CN double bond and trans to the terminal NH2 group. This latter group makes a single hydrogen bond with the S acceptor atom of a symmetry-related molecule [symmetry code: −1/2 + x, 1/2 − y, 1 − z; Table 1]. The two remaining potential N—H donors are not involved in any inter- or intra-molecular interactions and thus the hydrogen-bonding network within the crystal of (I) can be described as an extended chain along [100] (Fig. 2).

Interestingly, the solid-state structure of (I) reveals the presence of conformational disorder for the cycloheptane ring. Both the chair and boat conformations have been trapped randomly during the crystallization process and the chair conformation occurs in 63.6 (6)% of the molecules. The chair conformation of seven-membered rings is known to be more stable than the boat conformation by a few kcal mol−1 (Eliel et al., 1994; 1 kcal mol−1 = 4.184 kJ mol−1). Thus, the relative proportion of both conformers observed within the crystal of (I) may reflect the statistical partitioning of the two populations of cycloheptane structures corresponding to different energetic states.

Another point of interest is the comparison of the molecular structure of (I) with that of its parent compound, (II) (i.e. without the thiosemicarbazone substituent), which was reported by Auhmani et al. (1999). In this latter structure, no conformational disorder was observed and the cycloheptane ring adopts a boat conformation. The superposition of the boat conformation of (I) with compound (II) shows that they fit remarkably well: the r.m.s. deviation calculated with all pairs of corresponding C and Cl atoms of the three- and seven-membered rings, including the methyl substituents, is 0.070 Å. The main difference between the conformations of the two molecules is observed for the cyclohexene ring. The θ and ϕ puckering parameters for the cyclohexene ring of (II) [with the same reference atoms as used for (I)] are 53.5 (4) and 277.1 (4)°, respectively, and describe a distorted conformation between that of an envelope and a half-chair. The different hybridization character of the C atom, which bears the thiosemicarbazone moiety in (I) (sp2 hybridization) and two H atoms in (II) (sp3 hybridization) is responsible for this difference in ring conformation. On the basis of the superposition described above, we calculated the distance between C11 in (I) and its equivalent in (II) and found it to be 0.638 Å, while the five remaining atoms of the cyclohexene ring fit well (the mean distance between corresponding C atoms is 0.108 Å).

Experimental top

The dichlorocyclopropanation of β-himachalene, a major sesquiterpene isolated from the essential oil of Atlantical Cedrus, was carried out using 1 equivalent of chloroform and excess sodium hydroxide in phase-transfer catalysis liquid–solid at 273 K for 2 h. The product obtained was dissolved in tetrahydrofuran (50 ml) and oxidized with 2 equivalents of N-bromosuccinimide at 273 K for 1 h. The condensation of an equimolar quantity of the resultant ketone with thiosemicarbazide and several drops of hydrochloric acid in ethanol gave (I) in 60% yield after heating at reflux for 5 h. Suitable crystals were obtained by evaporation of a hexane solution at 277 K. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 9.80, 8.00, 7.40 (3H, NH2 and NH), 0.89 (3H, s), 1.01 (3H, s), 1.2–1.8 (6H, m), 4.90 (1H, d, J = 7.9 Hz), 1.82 (3H, s), 1.83 (3H, s), 2.60 (2H, AB system, J = 18.3 Hz); 13C NMR (CDCl3, δ, p.p.m.): 31.06 (C-1), 77.57 (C-2), 31.64 (C-3), 29.81 (C-4), 18.09 (C-5), 21.38 (C-6), 39.12 (C-7), 45.66 (C-8), 136.10 (C-9), 133.10 (C-10), 147.52 (C-11), 34.06 (C-12), 25.63 (C-13), 18.09 (C-14), 16.59 (C-15), 14.24 (C-16), 179.24 (CS).

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, N—H = 0.86 Å and Uiso(H) = 1.2Ueq(parent atom). Additionally, the methyl groups were allowed to rotate freely about their parent C—C bond. The disordered atoms in the cycloheptane ring were refined using the SADI, DELU and SAME instructions of SHELXL97 (Sheldrick, 1997) with an effective standard deviation of 0.005 in order to restrain the geometric parameters to chemically reasonable values. The site occupancy factors of the chair and boat conformations refined to 0.636 (5) and 0.364 (5), respectively.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of (I), showing the atom-labelling scheme. Both cycloheptane ring conformations are depicted, with the minor boat conformation drawn with open bonds. Displacement ellipsoids are drawn at the 30% probability level. H atoms bonded to C atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the crystal packing of (I), showing the hydrogen-bonding network. Only the chair conformation of the cycloheptane is represented.
(1S,3R,8R)-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01.3]dodecan- 11-one thiosemicarbazone top
Crystal data top
C17H25Cl2N3SF(000) = 792
Mr = 374.38Dx = 1.32 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 22028 reflections
a = 8.6379 (2) Åθ = 1.3–26.0°
b = 13.3638 (3) ŵ = 0.46 mm1
c = 16.3161 (3) ÅT = 293 K
V = 1883.49 (7) Å3Prism, colourless
Z = 40.6 × 0.6 × 0.4 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3499 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ϕ scansh = 1010
22028 measured reflectionsk = 1616
3671 independent reflectionsl = 1920
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.029P)2 + 0.5086P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.072(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.16 e Å3
3671 reflectionsΔρmin = 0.18 e Å3
237 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
18 restraintsExtinction coefficient: 0.033 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack & Bernardinelli (1999, 2000), with 1566 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.04 (5)
Crystal data top
C17H25Cl2N3SV = 1883.49 (7) Å3
Mr = 374.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6379 (2) ŵ = 0.46 mm1
b = 13.3638 (3) ÅT = 293 K
c = 16.3161 (3) Å0.6 × 0.6 × 0.4 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3499 reflections with I > 2σ(I)
22028 measured reflectionsRint = 0.036
3671 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.072Δρmax = 0.16 e Å3
S = 1.08Δρmin = 0.18 e Å3
3671 reflectionsAbsolute structure: Flack & Bernardinelli (1999, 2000), with 1566 Friedel pairs
237 parametersAbsolute structure parameter: 0.04 (5)
18 restraints
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.61062 (6)0.53553 (4)0.35727 (3)0.04938 (15)
Cl20.61678 (7)0.62823 (4)0.19869 (4)0.05206 (16)
S10.01291 (6)0.21029 (4)0.50781 (3)0.05093 (17)
N10.12818 (19)0.37322 (14)0.45567 (11)0.0481 (4)
H1A0.13270.42690.42670.058*
H1B0.20540.35630.48590.058*
N20.11387 (19)0.34842 (11)0.40459 (9)0.0379 (4)
H20.20140.31780.40330.045*
N30.08640 (18)0.43189 (12)0.35661 (10)0.0378 (4)
C10.4408 (2)0.45107 (13)0.22520 (10)0.0300 (4)
C20.5754 (2)0.51657 (14)0.25162 (12)0.0352 (4)
C30.6087 (2)0.41577 (13)0.21366 (11)0.0362 (4)
C40.6692 (3)0.41131 (19)0.12588 (14)0.0545 (6)
H4A0.65290.47500.10000.065*
H4B0.77780.39610.12620.065*
C50.5839 (4)0.3333 (2)0.07489 (16)0.0710 (8)
H5A0.56050.27640.10970.085*0.636 (6)
H5B0.65270.31000.03190.085*0.636 (6)
H5C0.59280.35260.01780.085*0.364 (6)
H5D0.63820.27020.08110.085*0.364 (6)
C70.2970 (3)0.40121 (15)0.08927 (12)0.0481 (5)
C6A0.4337 (4)0.3692 (3)0.0354 (2)0.0673 (14)0.636 (6)
H6A0.39730.31610.00020.081*0.636 (6)
H6B0.45950.42550.00050.081*0.636 (6)
C6B0.4135 (4)0.3143 (3)0.0926 (4)0.057 (2)0.364 (6)
H6C0.40690.28520.14700.068*0.364 (6)
H6D0.37820.26370.05430.068*0.364 (6)
C80.3504 (2)0.48616 (13)0.14951 (10)0.0337 (4)
H80.42100.52910.11830.040*
C90.2214 (2)0.55292 (14)0.17914 (12)0.0379 (4)
H90.19020.60480.14500.045*
C100.1493 (2)0.54300 (15)0.25042 (12)0.0379 (4)
C110.1893 (2)0.45791 (14)0.30361 (11)0.0330 (4)
C120.3412 (2)0.40487 (13)0.29175 (11)0.0326 (4)
H12A0.31770.33700.27710.039*
H12B0.39570.40580.34300.039*
C130.0209 (3)0.6120 (2)0.27749 (17)0.0658 (7)
H13A0.00700.66370.23740.079*
H13B0.04750.64150.32930.079*
H13C0.07330.57450.28310.079*
C140.6747 (3)0.33357 (16)0.26667 (14)0.0475 (5)
H14A0.78410.34370.27330.057*
H14B0.65670.27000.24110.057*
H14C0.62550.33480.31940.057*
C15A0.2146 (7)0.3138 (3)0.1300 (3)0.0659 (15)0.636 (6)
H15A0.13340.33870.16470.079*0.636 (6)
H15B0.28720.27650.16240.079*0.636 (6)
H15C0.17100.27110.08870.079*0.636 (6)
C16A0.1833 (6)0.4489 (3)0.0274 (3)0.0678 (14)0.636 (6)
H16A0.17080.40520.01880.081*0.636 (6)
H16B0.22370.51210.00920.081*0.636 (6)
H16C0.08480.45920.05330.081*0.636 (6)
C15B0.1433 (8)0.3536 (7)0.1163 (6)0.067 (2)0.364 (6)
H15D0.11590.30110.07880.081*0.364 (6)
H15E0.06340.40360.11640.081*0.364 (6)
H15F0.15450.32640.17040.081*0.364 (6)
C16B0.2840 (11)0.4424 (6)0.0025 (3)0.065 (2)0.364 (6)
H16D0.24380.39150.03310.077*0.364 (6)
H16E0.38450.46270.01630.077*0.364 (6)
H16F0.21550.49900.00230.077*0.364 (6)
C170.0033 (2)0.31704 (14)0.45372 (10)0.0352 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0489 (3)0.0556 (3)0.0436 (3)0.0026 (3)0.0091 (2)0.0099 (2)
Cl20.0539 (3)0.0342 (2)0.0681 (3)0.0107 (2)0.0020 (3)0.0086 (2)
S10.0381 (3)0.0578 (3)0.0569 (3)0.0008 (2)0.0042 (2)0.0279 (3)
N10.0329 (8)0.0568 (10)0.0548 (10)0.0037 (8)0.0086 (8)0.0220 (8)
N20.0290 (7)0.0429 (9)0.0418 (8)0.0017 (7)0.0057 (7)0.0127 (7)
N30.0348 (8)0.0397 (8)0.0391 (8)0.0008 (6)0.0035 (7)0.0099 (7)
C10.0333 (9)0.0279 (8)0.0290 (8)0.0002 (7)0.0026 (6)0.0011 (7)
C20.0346 (9)0.0323 (9)0.0388 (9)0.0000 (7)0.0005 (7)0.0014 (8)
C30.0352 (9)0.0338 (8)0.0394 (10)0.0037 (8)0.0081 (8)0.0000 (7)
C40.0552 (14)0.0595 (13)0.0488 (12)0.0096 (11)0.0204 (10)0.0007 (11)
C50.100 (2)0.0646 (15)0.0480 (13)0.0199 (15)0.0108 (14)0.0208 (12)
C70.0662 (14)0.0447 (11)0.0335 (10)0.0112 (10)0.0066 (10)0.0012 (9)
C6A0.100 (3)0.064 (2)0.038 (2)0.001 (2)0.0020 (19)0.0149 (19)
C6B0.091 (5)0.037 (3)0.041 (3)0.009 (3)0.002 (3)0.011 (3)
C80.0401 (9)0.0318 (8)0.0292 (8)0.0042 (7)0.0008 (7)0.0046 (7)
C90.0362 (10)0.0344 (9)0.0431 (10)0.0004 (8)0.0050 (8)0.0127 (8)
C100.0319 (9)0.0367 (9)0.0452 (10)0.0029 (8)0.0007 (8)0.0098 (8)
C110.0297 (8)0.0345 (9)0.0347 (9)0.0019 (8)0.0006 (7)0.0048 (8)
C120.0338 (9)0.0337 (9)0.0302 (8)0.0016 (7)0.0019 (7)0.0067 (7)
C130.0507 (14)0.0655 (15)0.0811 (17)0.0254 (12)0.0189 (13)0.0288 (13)
C140.0436 (11)0.0405 (10)0.0583 (13)0.0120 (9)0.0035 (10)0.0043 (10)
C15A0.107 (4)0.043 (2)0.049 (2)0.025 (2)0.018 (2)0.0053 (18)
C16A0.095 (4)0.067 (3)0.041 (2)0.021 (3)0.028 (2)0.0095 (19)
C15B0.088 (6)0.060 (5)0.054 (4)0.033 (5)0.004 (4)0.003 (4)
C16B0.075 (5)0.079 (5)0.039 (3)0.019 (4)0.002 (4)0.003 (3)
C170.0310 (9)0.0433 (10)0.0314 (8)0.0037 (8)0.0015 (7)0.0061 (7)
Geometric parameters (Å, º) top
Cl1—C21.769 (2)C7—C81.571 (3)
Cl2—C21.7608 (19)C6A—H6A0.9700
S1—C171.6833 (19)C6A—H6B0.9700
N1—C171.315 (3)C6B—H6C0.9700
N1—H1A0.8600C6B—H6D0.9700
N1—H1B0.8600C8—C91.507 (3)
N2—C171.357 (2)C8—H80.9800
N2—N31.383 (2)C9—C101.326 (3)
N2—H20.8600C9—H90.9300
N3—C111.288 (2)C10—C111.472 (2)
C1—C121.517 (2)C10—C131.508 (3)
C1—C21.518 (2)C11—C121.504 (2)
C1—C81.535 (2)C12—H12A0.9600
C1—C31.537 (3)C12—H12B0.9600
C2—C31.510 (2)C13—H13A0.9600
C3—C141.510 (3)C13—H13B0.9600
C3—C41.526 (3)C13—H13C0.9600
C4—C51.524 (4)C14—H14A0.9600
C4—H4A0.9600C14—H14B0.9600
C4—H4B0.9600C14—H14C0.9600
C5—C6B1.522 (4)C15A—H15A0.9600
C5—C6A1.526 (3)C15A—H15B0.9600
C5—H5A0.9700C15A—H15C0.9600
C5—H5B0.9700C16A—H16A0.9600
C5—H5C0.9700C16A—H16B0.9600
C5—H5D0.9700C16A—H16C0.9600
C7—C15A1.521 (3)C15B—H15D0.9600
C7—C16B1.523 (4)C15B—H15E0.9600
C7—C6A1.533 (3)C15B—H15F0.9600
C7—C15B1.537 (4)C16B—H16D0.9600
C7—C6B1.537 (4)C16B—H16E0.9600
C7—C16A1.546 (3)C16B—H16F0.9600
C17—N1—H1A120.0C7—C6B—H6C107.3
C17—N1—H1B120.0C5—C6B—H6D107.3
H1A—N1—H1B120.0C7—C6B—H6D107.3
C17—N2—N3117.09 (15)H6C—C6B—H6D106.9
C17—N2—H2121.5C9—C8—C1107.40 (14)
N3—N2—H2121.5C9—C8—C7114.30 (16)
C11—N3—N2118.63 (15)C1—C8—C7115.61 (15)
C12—C1—C2117.77 (15)C9—C8—H8106.3
C12—C1—C8114.31 (15)C1—C8—H8106.3
C2—C1—C8116.25 (15)C7—C8—H8106.3
C12—C1—C3119.87 (15)C10—C9—C8124.71 (16)
C2—C1—C359.26 (11)C10—C9—H9117.6
C8—C1—C3118.40 (15)C8—C9—H9117.6
C3—C2—C161.00 (12)C9—C10—C11118.95 (17)
C3—C2—Cl2121.06 (13)C9—C10—C13122.77 (18)
C1—C2—Cl2120.33 (13)C11—C10—C13118.19 (17)
C3—C2—Cl1119.64 (13)N3—C11—C10116.25 (16)
C1—C2—Cl1119.43 (13)N3—C11—C12124.15 (16)
Cl2—C2—Cl1108.76 (10)C10—C11—C12119.56 (15)
C14—C3—C2119.08 (16)C11—C12—C1113.28 (14)
C14—C3—C4112.33 (17)C11—C12—H12A107.1
C2—C3—C4119.02 (16)C1—C12—H12A109.0
C14—C3—C1120.64 (17)C11—C12—H12B108.0
C2—C3—C159.73 (12)C1—C12—H12B109.9
C4—C3—C1116.76 (17)H12A—C12—H12B109.5
C5—C4—C3111.9 (2)C10—C13—H13A109.5
C5—C4—H4A107.2C10—C13—H13B109.5
C3—C4—H4A109.2H13A—C13—H13B109.5
C5—C4—H4B109.3C10—C13—H13C109.5
C3—C4—H4B109.8H13A—C13—H13C109.5
H4A—C4—H4B109.5H13B—C13—H13C109.5
C6B—C5—C4118.5 (3)C3—C14—H14A109.5
C4—C5—C6A115.2 (3)C3—C14—H14B109.5
C4—C5—H5A108.5H14A—C14—H14B109.5
C6A—C5—H5A108.5C3—C14—H14C109.5
C4—C5—H5B108.5H14A—C14—H14C109.5
C6A—C5—H5B108.5H14B—C14—H14C109.5
H5A—C5—H5B107.5C7—C15A—H15A109.5
C6B—C5—H5C107.7C7—C15A—H15B109.5
C4—C5—H5C107.7H15A—C15A—H15B109.5
C6B—C5—H5D107.7C7—C15A—H15C109.5
C4—C5—H5D107.7H15A—C15A—H15C109.5
H5C—C5—H5D107.1H15B—C15A—H15C109.5
C15A—C7—C16B130.5 (4)C7—C16A—H16A109.5
C15A—C7—C6A113.4 (3)C7—C16A—H16B109.5
C16B—C7—C15B110.7 (5)H16A—C16A—H16B109.5
C6A—C7—C15B135.6 (4)C7—C16A—H16C109.5
C16B—C7—C6B110.8 (4)H16A—C16A—H16C109.5
C15B—C7—C6B104.0 (4)H16B—C16A—H16C109.5
C15A—C7—C16A107.8 (3)C7—C15B—H15D109.5
C6A—C7—C16A103.3 (3)C7—C15B—H15E109.5
C15A—C7—C8114.8 (2)H15D—C15B—H15E109.5
C16B—C7—C8110.0 (3)C7—C15B—H15F109.5
C6A—C7—C8109.5 (2)H15D—C15B—H15F109.5
C15B—C7—C8111.9 (4)H15E—C15B—H15F109.5
C6B—C7—C8109.3 (3)C7—C16B—H16D109.5
C16A—C7—C8107.3 (2)C7—C16B—H16E109.5
C5—C6A—C7120.1 (2)H16D—C16B—H16E109.5
C5—C6A—H6A107.3C7—C16B—H16F109.5
C7—C6A—H6A107.3H16D—C16B—H16F109.5
C5—C6A—H6B107.3H16E—C16B—H16F109.5
C7—C6A—H6B107.3N1—C17—N2116.72 (17)
H6A—C6A—H6B106.9N1—C17—S1122.64 (14)
C5—C6B—C7120.1 (3)N2—C17—S1120.63 (15)
C5—C6B—H6C107.3
C17—N2—N3—C11173.39 (17)C8—C7—C6B—C556.5 (5)
C12—C1—C2—C3109.99 (17)C12—C1—C8—C952.4 (2)
C8—C1—C2—C3108.89 (17)C2—C1—C8—C990.08 (18)
C12—C1—C2—Cl2138.96 (15)C3—C1—C8—C9157.68 (15)
C8—C1—C2—Cl22.2 (2)C12—C1—C8—C776.6 (2)
C3—C1—C2—Cl2111.05 (16)C2—C1—C8—C7140.98 (17)
C12—C1—C2—Cl10.3 (2)C3—C1—C8—C773.4 (2)
C8—C1—C2—Cl1141.44 (14)C15A—C7—C8—C975.7 (3)
C3—C1—C2—Cl1109.67 (15)C16B—C7—C8—C982.5 (5)
C1—C2—C3—C14110.5 (2)C6A—C7—C8—C9155.4 (2)
Cl2—C2—C3—C14139.59 (17)C15B—C7—C8—C940.9 (5)
Cl1—C2—C3—C141.2 (3)C6B—C7—C8—C9155.6 (2)
C1—C2—C3—C4105.8 (2)C16A—C7—C8—C944.0 (3)
Cl2—C2—C3—C44.1 (3)C15A—C7—C8—C149.7 (4)
Cl1—C2—C3—C4144.87 (17)C16B—C7—C8—C1152.0 (4)
Cl2—C2—C3—C1109.88 (16)C6A—C7—C8—C179.1 (2)
Cl1—C2—C3—C1109.32 (16)C15B—C7—C8—C184.6 (5)
C12—C1—C3—C141.5 (3)C6B—C7—C8—C130.1 (3)
C2—C1—C3—C14107.96 (19)C16A—C7—C8—C1169.4 (3)
C8—C1—C3—C14146.76 (18)C1—C8—C9—C1031.7 (2)
C12—C1—C3—C2106.47 (18)C7—C8—C9—C1098.0 (2)
C8—C1—C3—C2105.27 (17)C8—C9—C10—C113.8 (3)
C12—C1—C3—C4143.97 (18)C8—C9—C10—C13179.9 (2)
C2—C1—C3—C4109.56 (19)N2—N3—C11—C10175.92 (16)
C8—C1—C3—C44.3 (2)N2—N3—C11—C121.8 (3)
C14—C3—C4—C580.3 (2)C9—C10—C11—N3157.69 (19)
C2—C3—C4—C5133.7 (2)C13—C10—C11—N318.9 (3)
C1—C3—C4—C565.2 (2)C9—C10—C11—C1220.2 (3)
C3—C4—C5—C6B33.2 (4)C13—C10—C11—C12163.3 (2)
C3—C4—C5—C6A85.5 (3)N3—C11—C12—C1180.00 (18)
C4—C5—C6A—C763.9 (4)C10—C11—C12—C12.3 (2)
C15A—C7—C6A—C573.4 (4)C2—C1—C12—C11102.49 (18)
C16A—C7—C6A—C5170.3 (3)C8—C1—C12—C1139.4 (2)
C8—C7—C6A—C556.2 (4)C3—C1—C12—C11171.16 (15)
C4—C5—C6B—C756.5 (5)N3—N2—C17—N14.9 (3)
C16B—C7—C6B—C564.9 (6)N3—N2—C17—S1174.35 (13)
C15B—C7—C6B—C5176.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1i0.862.593.348 (2)147
Symmetry code: (i) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC17H25Cl2N3S
Mr374.38
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.6379 (2), 13.3638 (3), 16.3161 (3)
V3)1883.49 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.6 × 0.6 × 0.4
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22028, 3671, 3499
Rint0.036
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.072, 1.08
No. of reflections3671
No. of parameters237
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18
Absolute structureFlack & Bernardinelli (1999, 2000), with 1566 Friedel pairs
Absolute structure parameter0.04 (5)

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1i0.862.593.348 (2)147
Symmetry code: (i) x1/2, y+1/2, z+1.
 

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