2-(Methyl-sulfan-yl)cyclo-dodeca-none tosyl-hydrazone.

The title compound, C(20)H(32)N(2)O(2)S(2), has been synthesized by the reaction of α-methyl-sulfanylcyclo-dodeca-none and p-toluene-sulfonyl-hydrazine. In the crystal structure, the conformation of the non-benzenoid ring is [3333] and the methyl-sulfanyl group is in the α-side exo position. The mol-ecules are linked by inter-molecular N-H⋯S hydrogen bonds.

Related literature

For related literature, see: Li et al.(2005 ▶); Lu et al. (2004 ▶); Song et al. (2005 ▶); Wang et al. (2002 ▶, 2007 ▶).

Experimental

Crystal data

C20H32N2O2S2

M = 396.60

Monoclinic,

a = 8.4374 (7) Å

b = 11.5276 (10) Å

c = 21.7836 (19) Å

β = 92.530 (2)°

V = 2116.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 (2) K

0.47 × 0.38 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.778, T max = 1.000 (expected range = 0.722–0.929)

12199 measured reflections

4615 independent reflections

3650 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.131

S = 1.03

4615 reflections

241 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808005515/fl2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005515/fl2190Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H32N2O2S2	F000 = 856
Mr = 396.60	Dx = 1.245 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
a = 8.4374 (7) Å	Cell parameters from 3644 reflections
b = 11.5276 (10) Å	θ = 4.8–55.1º
c = 21.7836 (19) Å	µ = 0.27 mm−1
β = 92.530 (2)º	T = 293 (2) K
V = 2116.7 (3) Å3	Prismatic, colorless
Z = 4	0.47 × 0.38 × 0.28 mm

Bruker SMART CCD area-detector diffractometer	4615 independent reflections
Radiation source: fine-focus sealed tube	3650 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
T = 293(2) K	θmax = 27.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.778, Tmax = 1.000	k = −14→13
12199 measured reflections	l = −27→18

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.0655P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4615 reflections	Δρmax = 0.41 e Å−3
241 parameters	Δρmin = −0.23 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.84188 (7)	0.86341 (5)	0.29057 (3)	0.05522 (19)
S2	0.28829 (5)	1.10533 (4)	0.20128 (2)	0.03749 (15)
O1	0.24538 (17)	1.21632 (12)	0.17655 (6)	0.0515 (4)
O2	0.19940 (15)	1.00460 (12)	0.18414 (7)	0.0490 (4)
N1	0.53858 (18)	0.97987 (13)	0.19883 (7)	0.0360 (4)
N2	0.47071 (18)	1.08519 (14)	0.17949 (7)	0.0372 (4)
C1	0.6872 (2)	0.96614 (16)	0.19183 (8)	0.0358 (4)
C2	0.8013 (2)	1.05110 (18)	0.16582 (9)	0.0427 (5)
H2A	0.8964	1.0541	0.1925	0.051*
H2B	0.7536	1.1277	0.1655	0.051*
C3	0.8478 (2)	1.02089 (19)	0.10087 (9)	0.0471 (5)
H3A	0.9303	1.0739	0.0889	0.056*
H3B	0.8918	0.9431	0.1010	0.056*
C4	0.7115 (3)	1.0267 (2)	0.05364 (10)	0.0529 (6)
H4A	0.6746	1.1063	0.0507	0.063*
H4B	0.6249	0.9799	0.0678	0.063*
C5	0.7525 (3)	0.9853 (2)	−0.01033 (10)	0.0611 (6)
H5A	0.6654	1.0047	−0.0391	0.073*
H5B	0.8456	1.0269	−0.0229	0.073*
C6	0.7844 (3)	0.8560 (2)	−0.01425 (11)	0.0636 (7)
H6A	0.8664	0.8360	0.0165	0.076*
H6B	0.8255	0.8393	−0.0542	0.076*
C7	0.6409 (3)	0.7787 (2)	−0.00514 (11)	0.0666 (7)
H7A	0.5638	0.8216	0.0175	0.080*
H7B	0.5921	0.7598	−0.0451	0.080*
C8	0.6798 (3)	0.6672 (2)	0.02873 (12)	0.0710 (7)
H8A	0.7644	0.6280	0.0083	0.085*
H8B	0.5874	0.6172	0.0262	0.085*
C9	0.7308 (3)	0.6842 (2)	0.09646 (11)	0.0596 (6)
H9A	0.7750	0.6119	0.1123	0.072*
H9B	0.8141	0.7422	0.0993	0.072*
C10	0.5981 (3)	0.72134 (18)	0.13636 (10)	0.0491 (5)
H10A	0.5183	0.6607	0.1355	0.059*
H10B	0.5491	0.7904	0.1186	0.059*
C11	0.6475 (3)	0.74684 (18)	0.20316 (10)	0.0495 (5)
H11A	0.5527	0.7598	0.2259	0.059*
H11B	0.7006	0.6790	0.2206	0.059*
C12	0.7559 (2)	0.85050 (17)	0.21215 (9)	0.0434 (5)
H12	0.8455	0.8364	0.1860	0.052*
C13	0.6686 (3)	0.8781 (2)	0.33481 (11)	0.0699 (7)
H13A	0.6090	0.9447	0.3208	0.105*
H13B	0.7000	0.8877	0.3774	0.105*
H13C	0.6041	0.8099	0.3299	0.105*
C14	0.2972 (2)	1.11577 (16)	0.28203 (9)	0.0368 (4)
C15	0.3174 (2)	1.22352 (17)	0.30923 (9)	0.0429 (5)
H15	0.3252	1.2896	0.2851	0.051*
C16	0.3258 (2)	1.23198 (18)	0.37211 (10)	0.0485 (5)
H16	0.3384	1.3045	0.3903	0.058*
C17	0.3159 (3)	1.13478 (19)	0.40892 (10)	0.0481 (5)
C18	0.2959 (3)	1.02835 (18)	0.38062 (10)	0.0530 (6)
H18	0.2896	0.9622	0.4048	0.064*
C19	0.2849 (3)	1.01732 (17)	0.31766 (10)	0.0475 (5)
H19	0.2695	0.9450	0.2995	0.057*
C20	0.3224 (4)	1.1469 (2)	0.47810 (11)	0.0711 (7)
H20A	0.3608	1.2228	0.4893	0.107*
H20B	0.3924	1.0892	0.4959	0.107*
H20C	0.2180	1.1365	0.4931	0.107*
H2	0.522 (2)	1.1482 (14)	0.1827 (10)	0.049 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0623 (4)	0.0541 (4)	0.0480 (3)	0.0090 (3)	−0.0123 (3)	0.0002 (3)
S2	0.0374 (3)	0.0370 (3)	0.0381 (3)	0.00631 (19)	0.0012 (2)	−0.0006 (2)
O1	0.0597 (9)	0.0459 (8)	0.0486 (9)	0.0192 (7)	−0.0012 (7)	0.0047 (7)
O2	0.0430 (8)	0.0507 (8)	0.0529 (9)	−0.0030 (6)	−0.0030 (7)	−0.0071 (7)
N1	0.0418 (9)	0.0335 (8)	0.0328 (8)	0.0047 (7)	0.0035 (7)	0.0019 (6)
N2	0.0411 (9)	0.0334 (9)	0.0376 (9)	0.0032 (7)	0.0054 (7)	0.0024 (7)
C1	0.0411 (10)	0.0376 (10)	0.0287 (9)	0.0050 (8)	0.0016 (8)	−0.0046 (8)
C2	0.0384 (10)	0.0427 (11)	0.0473 (12)	−0.0002 (8)	0.0047 (9)	−0.0063 (9)
C3	0.0393 (10)	0.0561 (13)	0.0464 (12)	0.0003 (9)	0.0094 (9)	0.0025 (10)
C4	0.0492 (12)	0.0631 (15)	0.0466 (13)	0.0093 (11)	0.0049 (10)	0.0085 (11)
C5	0.0593 (14)	0.0856 (18)	0.0387 (12)	0.0064 (13)	0.0036 (11)	0.0137 (12)
C6	0.0608 (15)	0.0898 (19)	0.0408 (13)	0.0071 (13)	0.0102 (11)	−0.0017 (12)
C7	0.0725 (16)	0.0837 (18)	0.0426 (13)	0.0016 (14)	−0.0079 (12)	−0.0062 (13)
C8	0.0862 (19)	0.0698 (17)	0.0574 (16)	0.0073 (14)	0.0065 (14)	−0.0220 (13)
C9	0.0712 (15)	0.0528 (14)	0.0546 (14)	0.0144 (12)	0.0005 (12)	−0.0008 (11)
C10	0.0562 (13)	0.0407 (11)	0.0504 (13)	−0.0028 (10)	0.0011 (10)	−0.0023 (10)
C11	0.0623 (13)	0.0387 (11)	0.0476 (13)	0.0007 (10)	0.0046 (11)	0.0055 (9)
C12	0.0467 (11)	0.0448 (12)	0.0386 (11)	0.0081 (9)	0.0012 (9)	−0.0022 (9)
C13	0.099 (2)	0.0649 (16)	0.0459 (14)	0.0174 (14)	0.0083 (14)	−0.0074 (12)
C14	0.0350 (9)	0.0365 (10)	0.0395 (11)	0.0030 (8)	0.0065 (8)	0.0005 (8)
C15	0.0470 (11)	0.0355 (10)	0.0466 (12)	−0.0006 (9)	0.0078 (9)	0.0014 (9)
C16	0.0549 (12)	0.0418 (11)	0.0491 (13)	−0.0045 (10)	0.0067 (10)	−0.0073 (10)
C17	0.0495 (12)	0.0550 (13)	0.0402 (12)	−0.0020 (10)	0.0069 (10)	−0.0008 (10)
C18	0.0706 (14)	0.0430 (12)	0.0462 (13)	0.0004 (11)	0.0127 (11)	0.0095 (10)
C19	0.0621 (13)	0.0336 (10)	0.0476 (12)	0.0014 (9)	0.0116 (10)	−0.0019 (9)
C20	0.093 (2)	0.0784 (18)	0.0421 (13)	−0.0100 (15)	0.0074 (14)	−0.0047 (12)

S1—C13	1.794 (3)	C8—H8A	0.9700
S1—C12	1.832 (2)	C8—H8B	0.9700
S2—O2	1.4232 (14)	C9—C10	1.509 (3)
S2—O1	1.4287 (14)	C9—H9A	0.9700
S2—N2	1.6470 (16)	C9—H9B	0.9700
S2—C14	1.761 (2)	C10—C11	1.524 (3)
N1—C1	1.280 (2)	C10—H10A	0.9700
N1—N2	1.399 (2)	C10—H10B	0.9700
N2—H2	0.846 (15)	C11—C12	1.512 (3)
C1—C2	1.501 (3)	C11—H11A	0.9700
C1—C12	1.512 (3)	C11—H11B	0.9700
C2—C3	1.525 (3)	C12—H12	0.9800
C2—H2A	0.9700	C13—H13A	0.9600
C2—H2B	0.9700	C13—H13B	0.9600
C3—C4	1.510 (3)	C13—H13C	0.9600
C3—H3A	0.9700	C14—C19	1.382 (3)
C3—H3B	0.9700	C14—C15	1.383 (3)
C4—C5	1.527 (3)	C15—C16	1.372 (3)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.383 (3)
C5—C6	1.517 (3)	C16—H16	0.9300
C5—H5A	0.9700	C17—C18	1.380 (3)
C5—H5B	0.9700	C17—C20	1.512 (3)
C6—C7	1.524 (3)	C18—C19	1.376 (3)
C6—H6A	0.9700	C18—H18	0.9300
C6—H6B	0.9700	C19—H19	0.9300
C7—C8	1.510 (3)	C20—H20A	0.9600
C7—H7A	0.9700	C20—H20B	0.9600
C7—H7B	0.9700	C20—H20C	0.9600
C8—C9	1.531 (3)
C13—S1—C12	102.13 (11)	H8A—C8—H8B	107.6
O2—S2—O1	120.65 (9)	C10—C9—C8	114.0 (2)
O2—S2—N2	107.32 (8)	C10—C9—H9A	108.7
O1—S2—N2	104.01 (9)	C8—C9—H9A	108.7
O2—S2—C14	108.44 (9)	C10—C9—H9B	108.7
O1—S2—C14	108.32 (8)	C8—C9—H9B	108.7
N2—S2—C14	107.36 (9)	H9A—C9—H9B	107.6
C1—N1—N2	117.49 (15)	C9—C10—C11	115.22 (18)
N1—N2—S2	114.25 (12)	C9—C10—H10A	108.5
N1—N2—H2	121.3 (14)	C11—C10—H10A	108.5
S2—N2—H2	109.5 (15)	C9—C10—H10B	108.5
N1—C1—C2	127.74 (17)	C11—C10—H10B	108.5
N1—C1—C12	116.03 (17)	H10A—C10—H10B	107.5
C2—C1—C12	116.23 (16)	C12—C11—C10	114.46 (17)
C1—C2—C3	113.37 (16)	C12—C11—H11A	108.6
C1—C2—H2A	108.9	C10—C11—H11A	108.6
C3—C2—H2A	108.9	C12—C11—H11B	108.6
C1—C2—H2B	108.9	C10—C11—H11B	108.6
C3—C2—H2B	108.9	H11A—C11—H11B	107.6
H2A—C2—H2B	107.7	C1—C12—C11	115.91 (17)
C4—C3—C2	113.72 (17)	C1—C12—S1	109.40 (13)
C4—C3—H3A	108.8	C11—C12—S1	113.40 (15)
C2—C3—H3A	108.8	C1—C12—H12	105.8
C4—C3—H3B	108.8	C11—C12—H12	105.8
C2—C3—H3B	108.8	S1—C12—H12	105.8
H3A—C3—H3B	107.7	S1—C13—H13A	109.5
C3—C4—C5	114.30 (18)	S1—C13—H13B	109.5
C3—C4—H4A	108.7	H13A—C13—H13B	109.5
C5—C4—H4A	108.7	S1—C13—H13C	109.5
C3—C4—H4B	108.7	H13A—C13—H13C	109.5
C5—C4—H4B	108.7	H13B—C13—H13C	109.5
H4A—C4—H4B	107.6	C19—C14—C15	120.52 (19)
C6—C5—C4	114.00 (19)	C19—C14—S2	120.27 (15)
C6—C5—H5A	108.8	C15—C14—S2	119.21 (15)
C4—C5—H5A	108.8	C16—C15—C14	119.43 (18)
C6—C5—H5B	108.8	C16—C15—H15	120.3
C4—C5—H5B	108.8	C14—C15—H15	120.3
H5A—C5—H5B	107.6	C15—C16—C17	121.32 (19)
C5—C6—C7	115.0 (2)	C15—C16—H16	119.3
C5—C6—H6A	108.5	C17—C16—H16	119.3
C7—C6—H6A	108.5	C18—C17—C16	118.1 (2)
C5—C6—H6B	108.5	C18—C17—C20	121.7 (2)
C7—C6—H6B	108.5	C16—C17—C20	120.2 (2)
H6A—C6—H6B	107.5	C19—C18—C17	121.93 (19)
C8—C7—C6	113.8 (2)	C19—C18—H18	119.0
C8—C7—H7A	108.8	C17—C18—H18	119.0
C6—C7—H7A	108.8	C18—C19—C14	118.72 (19)
C8—C7—H7B	108.8	C18—C19—H19	120.6
C6—C7—H7B	108.8	C14—C19—H19	120.6
H7A—C7—H7B	107.7	C17—C20—H20A	109.5
C7—C8—C9	114.1 (2)	C17—C20—H20B	109.5
C7—C8—H8A	108.7	H20A—C20—H20B	109.5
C9—C8—H8A	108.7	C17—C20—H20C	109.5
C7—C8—H8B	108.7	H20A—C20—H20C	109.5
C9—C8—H8B	108.7	H20B—C20—H20C	109.5
C1—N1—N2—S2	−169.49 (13)	C10—C11—C12—C1	62.7 (2)
O2—S2—N2—N1	−51.04 (15)	C10—C11—C12—S1	−169.51 (15)
O1—S2—N2—N1	−179.96 (12)	C13—S1—C12—C1	70.58 (16)
C14—S2—N2—N1	65.37 (14)	C13—S1—C12—C11	−60.51 (17)
N2—N1—C1—C2	1.0 (3)	O2—S2—C14—C19	26.37 (19)
N2—N1—C1—C12	−178.92 (15)	O1—S2—C14—C19	158.95 (16)
N1—C1—C2—C3	−105.1 (2)	N2—S2—C14—C19	−89.30 (18)
C12—C1—C2—C3	74.8 (2)	O2—S2—C14—C15	−153.98 (15)
C1—C2—C3—C4	65.0 (2)	O1—S2—C14—C15	−21.41 (18)
C2—C3—C4—C5	−174.27 (19)	N2—S2—C14—C15	90.35 (16)
C3—C4—C5—C6	68.5 (3)	C19—C14—C15—C16	0.2 (3)
C4—C5—C6—C7	67.2 (3)	S2—C14—C15—C16	−179.41 (15)
C5—C6—C7—C8	−144.2 (2)	C14—C15—C16—C17	0.6 (3)
C6—C7—C8—C9	68.6 (3)	C15—C16—C17—C18	−0.5 (3)
C7—C8—C9—C10	70.6 (3)	C15—C16—C17—C20	−178.8 (2)
C8—C9—C10—C11	−176.03 (19)	C16—C17—C18—C19	−0.3 (3)
C9—C10—C11—C12	65.8 (2)	C20—C17—C18—C19	177.9 (2)
N1—C1—C12—C11	34.1 (2)	C17—C18—C19—C14	1.2 (3)
C2—C1—C12—C11	−145.82 (18)	C15—C14—C19—C18	−1.1 (3)
N1—C1—C12—S1	−95.61 (17)	S2—C14—C19—C18	178.55 (16)
C2—C1—C12—S1	84.45 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.846 (15)	2.786 (15)	3.6223 (18)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.846 (15)	2.786 (15)	3.6223 (18)	170 (2)

Symmetry code: (i) .