Crystal structure of (E)-N′-{[(1R,3R)-3-isopropyl-1-methyl-2-oxo­cyclo­pent­yl]methyl­idene}-4-methyl­benzene­sulfono­hydrazide

Tymann, D.; Dragon, D.C.; Golz, C.; Preut, H.; Strohmann, C.; Hiersemann, M.

doi:10.1107/S2056989014026747

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o99-o100

doi:10.1107/S2056989014026747

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Crystal structure of (E)-N′-{[(1R,3R)-3-isopropyl-1-methyl-2-oxocyclopentyl]methylidene}-4-methylbenzenesulfonohydrazide

David Tymann,^a Dina Christina Dragon,^a Christopher Golz,^a Hans Preut,^a ^* Carsten Strohmann ^a and Martin Hiersemann ^a

^aFakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
^*Correspondence e-mail: hans.preut@tu-dortmund.de

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 25 November 2014; accepted 5 December 2014; online 10 January 2015)

The title compound, C₁₇H₂₄N₂O₃S, was synthesized in order to determine the relative configuration of the corresponding β-keto aldehyde. In the U-shaped molecule, the five-membered ring approximates an envelope with the methylene atom adjacent to the quaternary C atom being the flap. The dihedral angles between the four nearly coplanar atoms of the five-membered ring and the flap and the aromatic ring are 38.8 (4) and 22.9 (2)°, respectively. The bond angles around the S atom are in the range 104.11 (16)–119.95 (16)°. In the crystal, molecules are linked via N—H⋯O by hydrogen bonds, forming a chain along the a-axis direction.

Keywords: crystal structure; benzenesulfonohydrazide; terpenoid-related building blocks; hydrogen bonding; cyclopentanoids.

CCDC reference: 1437665

1. Related literature

For the synthesis of terpenoid-related building blocks, in particular cyclopentanoids, see: Becker et al. (2013 ); Gille et al. (2011 ); Helmboldt et al. (2006 ); Nelson et al. (2011 ); Tymann et al.(2014 ). For a review on cyclopentanoids by ring contraction see: Silva (2002 ). For a solid–acid catalysed rearrangement of cyclic α,β-epoxy ketones see: Elings et al. (2000 ).

2. Experimental

2.1. Crystal data

C₁₇H₂₄N₂O₃S
M_r = 336.44
Monoclinic, P 2₁
a = 6.6198 (8) Å
b = 16.8318 (18) Å
c = 7.9506 (9) Å
β = 97.141 (11)°
V = 879.00 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.23 × 0.10 × 0.03 mm

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.98, T_max = 1.00
6620 measured reflections
3684 independent reflections
3185 reflections with I > 2σ(I)
R_int = 0.032

2.3. Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.091
S = 1.01
3684 reflections
216 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack x determined using 1307 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack,2004 )
Absolute structure parameter: 0.02 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.91 (4)	2.03 (4)	2.889 (4)	158 (3)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1437665

Crystal structure: contains datablocks I, 2864. DOI: 10.1107/S2056989014026747/tk5349sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989014026747/tk5349Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989014026747/tk5349Isup3.cml

checkCIF report

Comment top

Prompted by our efforts in natural product synthesis, we seek access to cyclopentyl units. Herein, we chosed a ring contraction strategy of a cyclic epoxy ketone. A Brønsted-acid promoted [1,2]-sigmatropic rearrangement of cis-piperitone oxide delivered trans-3-Isopropyl-1-methyl-2-oxocyclopentane-1-carbaldehyde (II). A subsequent condensation of (II) with p-toulenesulfonyl hydrazide afforded the title compound (I).

Related literature top

For the synthesis of terpenoid-related building blocks, in particular cyclopentanoids, see: Becker et al. (2013); Gille et al. (2011); Helmboldt et al. (2006); Nelson et al. (2011); Tymann et al.(2014). For a review on cyclopentanoids by ring contraction see: Silva (2002). For a solid–acid catalysed rearrangement of cyclic α,β-epoxy ketones see: Elings et al. (2000).

Experimental top

A sealable glass pressure tube was charged with a solution of trans-3-Isopropyl-1-methyl-2-oxocyclopentane-1-carbaldehyde (II) (C₁₀H₁₆O₂, M = 168.23 g/mol, [α]_D²⁰ = +248.3 (c 0.059 mol/L, CHCl₃), 150 mg, 0.89 mmol, 1.0 eq) and p-toluenesulfonyl hydrazide (C₇H₁₀N₂O₂S, M = 186.23 g/mol, 232 mg, 1.24 mmol, 1.4 eq) in methanol (9 ml, 10.1 ml/mmol). The tube was sealed with a Teflon screw cap and placed in a pre-heated oil bath (353 K). After being stirred for 2.5 h at 353 K, the reaction mixture was cooled to ambient temperature and stirred for additional 16 h at room temperature. Next, the volatiles were removed under reduced pressure. Purification of the residue by flash chromatography (cyclohexane/ethyl acetate 50/1 to 5/1) delivered the title compound (I) (C₁₇H₂₄N₂O₃S, M = 336.45 g/mol, 161 mg, 0.48 mmol, 54%) as a white solid and as an apparent mixture of double bond isomers (ratio = 68:32). Subsequent recrystallization of (I) from n-pentane provided colourless plates of the E-configured double bond isomer of (I). The ratio of isomers was determined by integration of the ¹H NMR signals at 6.66 p.p.m. (s, 1H) and 7.12 p.p.m. (s, 1H). Characterization data are reported for the mixture of isomers. R_f 0.44 (cyclohexane/ethyl acetate 2/1); m.p. 361–363 K; ¹H NMR (CDCl₃, 500 MHz, ratio of double bond isomers = 68:32) δ 0.81 (d, J = 6.7 Hz, 3H^major), 0.93 (d, J = 6.9 Hz, 3H^minor), 0.97 (d, J = 6.7 Hz, 3H^major), 1.08–1.09 (m, 3H^major+3H^minor), 1.12 (s, 3H^minor), 1.52–1.59 (m, 1H^minor), 1.62–1.81 (m, 2H^major+3H^minor), 1.93–2.02 (m, 1H^major), 2.05–2.23 (m, 3H^major+1H^minor), 2.42 (s, 3H^minor), 2.43 (s, 3H^major), 2.53–2.56 (m, 1H^minor), 6.66 (s, 1H^minor), 7.12 (s 1H^minor), 7.29–7.32 (m, 2H^major+2H^minor), 7.58 (br. s, 1H), 7.70 (br. s, 1H), 7.79 (d, J = 8.2 Hz, 2H^major), 7.84 (d, J = 8.2 Hz, 2H^minor); ¹³C NMR (CDCl₃, 126 MHz) δ 16.9 (CH₃^minor), 18.5 (CH₃^major), 19.3 (CH₃^minor), 20.1 (CH₃^major), 20.5 (CH₂^major), 20.9 (CH₃^major), 21.57 (CH₃^minor), 21.59 (CH₃^major), 23.7 (CH₃^minor), 24.3 (CH₂^minor), 26.2 (CH^major), 27.3 (CH^minor), 31.4 (CH₂^major), 35.8 (CH₂^minor), 53.1 (C^major), 55.2 (CH^minor), 55.3 (CH^major), 61.9 (C^minor), 127.8 (CH^minor), 127.9 (CH^major), 129.4 (CH^minor), 129.5 (CH^major), 135.1 (C^major), 136.6 (C^minor), 134.8 (C^minor), 144.2 (C^major), 152.8 (CH^major), 154.0 (CH^minor), 218.9 (C^major+C^minor); IR ν 3445 (m), 3175 (m), 2960 (m), 2360 (w), 1730 (s), 1595 (m), 1470 (m), 1355 (s), 1320 (m), 1185 (s), 1165 (s), 1093 (m), 815 (s); Anal. Calcd. for C₁₇H₂₄N₂O₃S: C, 60.7; H, 7.2; N, 8.3; Found: C, 60.9; H, 7.2; N, 8.1.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. : The molecular structure of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 30% probability level.

(E)-N'-{[(1R,3R)-3-Isopropyl-1-methyl-2-oxocyclopentyl]methylidene}-4-methylbenzenesulfonohydrazide top

Crystal data top

C₁₇H₂₄N₂O₃S	Z = 2
M_r = 336.44	F(000) = 360
Monoclinic, P2₁	D_x = 1.271 Mg m⁻³
a = 6.6198 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.8318 (18) Å	µ = 0.20 mm⁻¹
c = 7.9506 (9) Å	T = 173 K
β = 97.141 (11)°	Plate, colourless
V = 879.00 (17) Å³	0.23 × 0.10 × 0.03 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3684 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3185 reflections with I > 2σ(I)
Detector resolution: 16.0560 pixels mm^-1	R_int = 0.032
phi and ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2008)	h = −7→8
T_min = 0.98, T_max = 1.00	k = −21→21
6620 measured reflections	l = −10→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0406P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3684 reflections	Δρ_max = 0.21 e Å⁻³
216 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 1307 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack,2004)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

C₁₇H₂₄N₂O₃S	V = 879.00 (17) Å³
M_r = 336.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.6198 (8) Å	µ = 0.20 mm⁻¹
b = 16.8318 (18) Å	T = 173 K
c = 7.9506 (9) Å	0.23 × 0.10 × 0.03 mm
β = 97.141 (11)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3684 independent reflections
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2008)	3185 reflections with I > 2σ(I)
T_min = 0.98, T_max = 1.00	R_int = 0.032
6620 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.21 e Å⁻³
S = 1.01	Δρ_min = −0.29 e Å⁻³
3684 reflections	Absolute structure: Flack x determined using 1307 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack,2004)
216 parameters	Absolute structure parameter: 0.02 (5)
1 restraint

Special details top

Experimental. Absorption correction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.24 (release 03–12-2012 CrysAlis171. NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
S	0.09218 (13)	0.45682 (4)	0.12604 (10)	0.0211 (2)
O1	0.2056 (4)	0.41202 (15)	0.0179 (3)	0.0301 (7)
O2	−0.1089 (4)	0.43231 (14)	0.1507 (3)	0.0328 (7)
O3	0.7126 (4)	0.64917 (14)	0.0645 (3)	0.0263 (6)
N1	0.0612 (5)	0.54744 (16)	0.0481 (4)	0.0201 (7)
N2	0.2410 (4)	0.59285 (16)	0.0665 (4)	0.0190 (6)
C1	0.6011 (7)	0.4966 (3)	0.8060 (5)	0.0363 (10)
H1A	0.6121	0.5531	0.8347	0.054*
H1B	0.7374	0.4746	0.8012	0.054*
H1C	0.5358	0.4684	0.8926	0.054*
C2	0.4754 (6)	0.4867 (2)	0.6364 (5)	0.0233 (8)
C4	0.4451 (5)	0.4458 (2)	0.3415 (4)	0.0209 (8)
H4	0.5048	0.4249	0.2483	0.025*
C3	0.5595 (5)	0.4551 (2)	0.4991 (4)	0.0233 (7)
H3	0.6986	0.4396	0.5133	0.028*
C5	0.2427 (5)	0.46758 (19)	0.3241 (4)	0.0185 (7)
C6	0.1547 (6)	0.4995 (2)	0.4585 (5)	0.0251 (8)
H6	0.0157	0.5151	0.4435	0.030*
C7	0.2701 (6)	0.5084 (2)	0.6137 (5)	0.0277 (9)
H7	0.2095	0.5295	0.7063	0.033*
C8	0.2181 (5)	0.66745 (19)	0.0519 (4)	0.0190 (7)
H8	0.0848	0.6889	0.0286	0.023*
C9	0.3979 (6)	0.7225 (2)	0.0708 (5)	0.0206 (8)
C10	0.5880 (5)	0.67705 (19)	0.1474 (5)	0.0199 (8)
C11	0.6049 (6)	0.6771 (2)	0.3399 (5)	0.0229 (8)
H11	0.5766	0.6223	0.3794	0.027*
C12	0.8215 (6)	0.7019 (2)	0.4184 (5)	0.0260 (9)
H12	0.9204	0.6689	0.3633	0.031*
C13	0.8553 (7)	0.6835 (3)	0.6095 (5)	0.0462 (12)
H13A	0.9966	0.6954	0.6544	0.069*
H13B	0.8275	0.6271	0.6276	0.069*
H13C	0.7633	0.7161	0.6681	0.069*
C14	0.8694 (6)	0.7886 (2)	0.3864 (5)	0.0331 (10)
H14A	0.7745	0.8227	0.4385	0.050*
H14B	0.8555	0.7986	0.2641	0.050*
H14C	1.0091	0.8005	0.4361	0.050*
C15	0.4298 (6)	0.7325 (2)	0.3774 (5)	0.0283 (9)
H15A	0.3113	0.7012	0.4040	0.034*
H15B	0.4747	0.7677	0.4747	0.034*
C16	0.3749 (6)	0.7811 (2)	0.2166 (5)	0.0282 (9)
H16A	0.4683	0.8268	0.2132	0.034*
H16B	0.2334	0.8011	0.2095	0.034*
C17	0.4217 (6)	0.7612 (2)	−0.0986 (5)	0.0296 (10)
H17A	0.4403	0.7200	−0.1823	0.044*
H17B	0.5406	0.7964	−0.0853	0.044*
H17C	0.2994	0.7923	−0.1372	0.044*
H1N	−0.051 (6)	0.572 (2)	0.079 (5)	0.027 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0204 (5)	0.0192 (4)	0.0219 (4)	−0.0035 (4)	−0.0047 (3)	0.0012 (4)
O1	0.0387 (18)	0.0257 (13)	0.0233 (14)	0.0052 (12)	−0.0065 (13)	−0.0048 (11)
O2	0.0232 (16)	0.0337 (15)	0.0382 (16)	−0.0125 (11)	−0.0090 (12)	0.0108 (12)
O3	0.0152 (14)	0.0305 (14)	0.0335 (15)	0.0027 (11)	0.0039 (12)	−0.0092 (12)
N1	0.0120 (16)	0.0218 (16)	0.0252 (17)	−0.0016 (12)	−0.0024 (13)	0.0021 (13)
N2	0.0129 (16)	0.0229 (15)	0.0209 (16)	−0.0022 (12)	0.0005 (12)	0.0003 (12)
C1	0.046 (3)	0.032 (2)	0.027 (2)	−0.004 (2)	−0.009 (2)	−0.0023 (18)
C2	0.029 (2)	0.0184 (18)	0.021 (2)	−0.0061 (15)	−0.0019 (17)	0.0027 (14)
C4	0.0215 (19)	0.0194 (19)	0.0217 (17)	0.0011 (16)	0.0023 (14)	0.0007 (15)
C3	0.0167 (17)	0.0217 (16)	0.0296 (18)	0.0004 (17)	−0.0053 (14)	0.0021 (19)
C5	0.0200 (18)	0.0157 (18)	0.0188 (16)	−0.0015 (14)	−0.0018 (14)	0.0005 (14)
C6	0.020 (2)	0.0289 (19)	0.026 (2)	0.0013 (16)	0.0034 (17)	0.0025 (16)
C7	0.034 (2)	0.028 (2)	0.021 (2)	0.0013 (17)	0.0071 (18)	−0.0025 (16)
C8	0.0119 (18)	0.0218 (18)	0.0229 (18)	0.0016 (14)	0.0008 (14)	−0.0003 (15)
C9	0.0154 (19)	0.0183 (18)	0.029 (2)	−0.0004 (14)	0.0039 (16)	0.0001 (15)
C10	0.014 (2)	0.0154 (17)	0.031 (2)	−0.0055 (14)	0.0051 (16)	−0.0030 (15)
C11	0.019 (2)	0.0229 (19)	0.027 (2)	−0.0016 (15)	0.0032 (16)	0.0008 (16)
C12	0.017 (2)	0.035 (2)	0.026 (2)	0.0014 (15)	0.0024 (17)	−0.0061 (17)
C13	0.037 (3)	0.067 (3)	0.034 (3)	−0.001 (2)	0.000 (2)	−0.002 (2)
C14	0.021 (2)	0.038 (2)	0.041 (2)	−0.0060 (17)	0.0044 (19)	−0.0082 (19)
C15	0.021 (2)	0.035 (2)	0.030 (2)	−0.0016 (17)	0.0063 (17)	−0.0097 (18)
C16	0.020 (2)	0.0221 (18)	0.043 (2)	0.0017 (15)	0.0068 (18)	−0.0071 (17)
C17	0.024 (2)	0.028 (2)	0.037 (2)	0.0000 (16)	0.0047 (19)	0.0094 (17)

Geometric parameters (Å, º) top

S—O1	1.426 (3)	C9—C17	1.522 (5)
S—O2	1.431 (3)	C9—C10	1.533 (5)
S—N1	1.649 (3)	C9—C16	1.544 (5)
S—C5	1.765 (3)	C10—C11	1.520 (5)
O3—C10	1.213 (4)	C11—C15	1.546 (5)
N1—N2	1.407 (4)	C11—C12	1.548 (5)
N1—H1N	0.91 (4)	C11—H11	1.0000
N2—C8	1.268 (4)	C12—C14	1.522 (6)
C1—C2	1.503 (5)	C12—C13	1.539 (5)
C1—H1A	0.9800	C12—H12	1.0000
C1—H1B	0.9800	C13—H13A	0.9800
C1—H1C	0.9800	C13—H13B	0.9800
C2—C3	1.391 (5)	C13—H13C	0.9800
C2—C7	1.398 (5)	C14—H14A	0.9800
C4—C5	1.380 (5)	C14—H14B	0.9800
C4—C3	1.390 (5)	C14—H14C	0.9800
C4—H4	0.9500	C15—C16	1.523 (6)
C3—H3	0.9500	C15—H15A	0.9900
C5—C6	1.387 (5)	C15—H15B	0.9900
C6—C7	1.376 (5)	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—H7	0.9500	C17—H17A	0.9800
C8—C9	1.501 (5)	C17—H17B	0.9800
C8—H8	0.9500	C17—H17C	0.9800

O1—S—O2	119.95 (16)	O3—C10—C9	123.9 (3)
O1—S—N1	108.22 (16)	C11—C10—C9	110.7 (3)
O2—S—N1	104.11 (16)	C10—C11—C15	103.4 (3)
O1—S—C5	108.13 (16)	C10—C11—C12	110.8 (3)
O2—S—C5	109.82 (16)	C15—C11—C12	116.0 (3)
N1—S—C5	105.67 (15)	C10—C11—H11	108.8
N2—N1—S	113.5 (2)	C15—C11—H11	108.8
N2—N1—H1N	116 (2)	C12—C11—H11	108.8
S—N1—H1N	113 (2)	C14—C12—C13	110.5 (3)
C8—N2—N1	116.0 (3)	C14—C12—C11	113.1 (3)
C2—C1—H1A	109.5	C13—C12—C11	110.9 (3)
C2—C1—H1B	109.5	C14—C12—H12	107.3
H1A—C1—H1B	109.5	C13—C12—H12	107.3
C2—C1—H1C	109.5	C11—C12—H12	107.3
H1A—C1—H1C	109.5	C12—C13—H13A	109.5
H1B—C1—H1C	109.5	C12—C13—H13B	109.5
C3—C2—C7	118.4 (3)	H13A—C13—H13B	109.5
C3—C2—C1	121.0 (4)	C12—C13—H13C	109.5
C7—C2—C1	120.6 (4)	H13A—C13—H13C	109.5
C5—C4—C3	118.3 (3)	H13B—C13—H13C	109.5
C5—C4—H4	120.8	C12—C14—H14A	109.5
C3—C4—H4	120.8	C12—C14—H14B	109.5
C4—C3—C2	121.6 (3)	H14A—C14—H14B	109.5
C4—C3—H3	119.2	C12—C14—H14C	109.5
C2—C3—H3	119.2	H14A—C14—H14C	109.5
C4—C5—C6	121.4 (3)	H14B—C14—H14C	109.5
C4—C5—S	119.7 (3)	C16—C15—C11	105.5 (3)
C6—C5—S	118.8 (3)	C16—C15—H15A	110.6
C7—C6—C5	119.5 (3)	C11—C15—H15A	110.6
C7—C6—H6	120.2	C16—C15—H15B	110.6
C5—C6—H6	120.2	C11—C15—H15B	110.6
C6—C7—C2	120.7 (3)	H15A—C15—H15B	108.8
C6—C7—H7	119.7	C15—C16—C9	104.6 (3)
C2—C7—H7	119.7	C15—C16—H16A	110.8
N2—C8—C9	121.2 (3)	C9—C16—H16A	110.8
N2—C8—H8	119.4	C15—C16—H16B	110.8
C9—C8—H8	119.4	C9—C16—H16B	110.8
C8—C9—C17	110.1 (3)	H16A—C16—H16B	108.9
C8—C9—C10	109.5 (3)	C9—C17—H17A	109.5
C17—C9—C10	113.3 (3)	C9—C17—H17B	109.5
C8—C9—C16	108.5 (3)	H17A—C17—H17B	109.5
C17—C9—C16	114.9 (3)	C9—C17—H17C	109.5
C10—C9—C16	100.0 (3)	H17A—C17—H17C	109.5
O3—C10—C11	125.3 (3)	H17B—C17—H17C	109.5

O1—S—N1—N2	−71.4 (3)	N2—C8—C9—C10	−13.1 (5)
O2—S—N1—N2	159.9 (2)	N2—C8—C9—C16	−121.3 (3)
C5—S—N1—N2	44.2 (3)	C8—C9—C10—O3	97.8 (4)
S—N1—N2—C8	−161.8 (3)	C17—C9—C10—O3	−25.6 (5)
C5—C4—C3—C2	−0.9 (5)	C16—C9—C10—O3	−148.4 (3)
C7—C2—C3—C4	0.7 (5)	C8—C9—C10—C11	−86.2 (4)
C1—C2—C3—C4	−179.9 (3)	C17—C9—C10—C11	150.5 (3)
C3—C4—C5—C6	1.2 (5)	C16—C9—C10—C11	27.7 (4)
C3—C4—C5—S	179.9 (3)	O3—C10—C11—C15	169.9 (3)
O1—S—C5—C4	10.2 (3)	C9—C10—C11—C15	−6.1 (4)
O2—S—C5—C4	142.7 (3)	O3—C10—C11—C12	45.0 (5)
N1—S—C5—C4	−105.5 (3)	C9—C10—C11—C12	−131.0 (3)
O1—S—C5—C6	−171.1 (3)	C10—C11—C12—C14	68.4 (4)
O2—S—C5—C6	−38.5 (3)	C15—C11—C12—C14	−49.0 (4)
N1—S—C5—C6	73.2 (3)	C10—C11—C12—C13	−166.7 (3)
C4—C5—C6—C7	−1.2 (5)	C15—C11—C12—C13	75.8 (4)
S—C5—C6—C7	−179.9 (3)	C10—C11—C15—C16	−18.9 (4)
C5—C6—C7—C2	0.9 (6)	C12—C11—C15—C16	102.6 (4)
C3—C2—C7—C6	−0.7 (5)	C11—C15—C16—C9	37.0 (4)
C1—C2—C7—C6	179.9 (3)	C8—C9—C16—C15	75.9 (4)
N1—N2—C8—C9	179.3 (3)	C17—C9—C16—C15	−160.4 (3)
N2—C8—C9—C17	112.1 (4)	C10—C9—C16—C15	−38.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.91 (4)	2.03 (4)	2.889 (4)	158 (3)

Symmetry code: (i) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.91 (4)	2.03 (4)	2.889 (4)	158 (3)

Symmetry code: (i) x−1, y, z.

Acknowledgements

Financial support obtained from the Beilstein Institut is gratefully acknowledged

References

Becker, J., Butt, L., von Kiedrowski, V., Mischler, E., Quentin, F. & Hiersemann, M. (2013). Org. Lett. 15, 5982–5985. Web of Science CrossRef CAS PubMed Google Scholar
Elings, J. A., Lempers, H. E. B. & Sheldon, R. A. (2000). Eur. J. Org. Chem. pp. 1905–1911. Google Scholar
Gille, A., Rehbein, J. & Hiersemann, M. (2011). Org. Lett. 13, 2122–2125. Web of Science CrossRef CAS PubMed Google Scholar
Helmboldt, H., Köhler, D. & Hiersemann, M. (2006). Org. Lett. 8, 1573–1576. Web of Science CSD CrossRef PubMed CAS Google Scholar
Nelson, B., Hiller, W., Pollex, A. & Hiersemann, M. (2011). Org. Lett. 13, 4438–4441. Web of Science CrossRef CAS PubMed Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, L. F. Jr (2002). Tetrahedron, 58, 9137–9161. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tymann, D., Klüppel, A., Hiller, W. & Hiersemann, M. (2014). Org. Lett. 16, 4062–4065. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 71| Part 2| February 2015| Pages o99-o100

doi:10.1107/S2056989014026747

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-N′-{[(1R,3R)-3-iso­propyl-1-methyl-2-oxo­cyclo­pent­yl]methyl­­idene}-4-methyl­benzene­sulfono­hydrazide

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (E)-N′-{[(1R,3R)-3-isopropyl-1-methyl-2-oxocyclopentyl]methylidene}-4-methylbenzenesulfonohydrazide