Crystal structure of N′-[(E)-(1S,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/S2056989015020307

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o904-o905

https://doi.org/10.1107/S2056989015020307

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Crystal structure of N′-[(E)-(1S,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 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 20 October 2015; accepted 27 October 2015; online 4 November 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 C atom adjacent to the quaternary C atom being the flap, and the methyl and isopropyl substituents lying to the same side of the ring. The dihedral angles between the four nearly coplanar atoms of the five-membered ring and the flap and the aromatic ring are 35.74 (15) and 55.72 (9)°, respectively. The bond angles around the S atom are in the range from 103.26 (12) to 120.65 (14)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming a chain along the a axis.

Keywords: crystal structure; hydrogen bonding; terpenoid synthesis.

CCDC reference: 1037859

1. Related literature

For the synthesis of terpenoid-related buildings blocks, in particular cyclopentanoids, see: Helmboldt et al. (2006 ); Gille et al. (2011 ); Becker et al. (2013 ); Tymann et al. (2014 ). For the crystal structure of the corresponding trans-diastereomer, see: Tymann et al. (2015 ). 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
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.4918 (7) Å
b = 13.2348 (12) Å
c = 14.6691 (12) Å
V = 1842.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.31 × 0.25 × 0.23 mm

2.2. Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.98, T_max = 1.00
15093 measured reflections
4215 independent reflections
3526 reflections with I > 2σ(I)
R_int = 0.046

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.093
S = 1.05
4215 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack x determined using 1277 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004 )
Absolute structure parameter: −0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.86 (3)	2.00 (4)	2.836 (3)	164 (3)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1037859

Crystal structure: contains datablocks I, 2887. DOI: https://doi.org/10.1107/S2056989015020307/tk5399sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015020307/tk5399Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020307/tk5399Isup3.cml

checkCIF report

Comment top

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

Related literature top

For the synthesis of terpenoid-related buildings blocks, in particular cyclopentanoids, see: Helmboldt et al. (2006); Gille et al. (2011); Becker et al. (2013); Tymann et al. (2014). For the crystal structure of the corresponding trans-diastereomer, see: Tymann et al. (2015). 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 cis-3-isopropyl-1-methyl-2-oxocyclopentane-1-carbaldehyde (II) (C₁₀H₁₆O₂, M = 168.23 g/mol, [α]_D²⁰ = -107.4 (c 0.059, CHCl₃), 40 mg, 0.238 mmol, 1.0 eq) and p-toluenesulfonyl hydrazide (C₇H₁₀N₂O₂S, M = 186.23 g/mol, 62 mg, 0.333 mmol, 1.4 eq) in methanol (3 ml, 12.6 ml/mmol). The tube was sealed with a Teflon screw cap and stirred for 75 min at ambient temperature. Next, the reaction mixture was concentrated in vacuo and loaded onto silica gel with CH₂Cl₂ for flash chromatography (cyclohexane/ethyl acetate 10/1) to deliver the title compound (I) (C₁₇H₂₄N₂O₃S, M = 336.45 g/mol, 56 mg, 0.166 mmol, 70%) as a white solid and as an apparent mixture of double bond isomers (ratio = 95:5). Subsequent recrystallization of (I) from n-pentane/Et₂O provided colourless crystals of the E-configured double bond isomer of (I). The ratio of isomers was determined by integration of the ¹H NMR signals at 0.35 p.p.m. (d, J = 6.9 Hz, 3H) and 0.47 p.p.m. (d, J = 6.9 Hz, 3H). Characterization data are reported for the major compound from the mixture of double bond isomers. R_f 0.41 (cyclohexane/ethyl acetate 2/1); m.p. 388–391 K; ¹H NMR (CDCl₃, 500 MHz) δ 0.47 (d, J = 6.9 Hz, 3H), 0.85 (d, J = 6.9 Hz, 3H), 1.16 (s, 3H), 1.48–1.59 (m, 2H), 1.82–1.95 (m, 2H), 2.11 (td, J = 9.4 Hz, J = 5.0 Hz, 1H), 2.42 (s, 3H), 2.49–2.53 (m, 1H), 6.88 (s, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 2H), 7.89 (s, 1H). ¹³C NMR (CDCl₃, 126 MHz) δ 18.4 (CH₃), 20.8 (CH₃), 21.2 (CH₂), 21.5 (CH₃), 21.9 (CH₃), 27.8 (CH), 31.6 (CH₂), 53.8 (C), 54.7 (CH), 128.0 (2x CH), 129.6 (2x CH), 135.1 (C), 144.2 (C), 150.6 (CH), 219.1 (C). IR ν 3415 (w), 3126 (s), 2960 (s), 22870 (s), 1725 (s), 1600 (m), 1455 (s), 1360 (s), 1330 (m), 1170 (s), 1095 (m), 1050 (s), 940 (m) 820 (s); Anal. Calcd. for C₁₇H₂₄N₂O₃S: C, 60.7, H, 7.2, N, 8.3. Found: C, 60.6, H, 7.3, N, 8.3.

Structure description top

For the synthesis of terpenoid-related buildings blocks, in particular cyclopentanoids, see: Helmboldt et al. (2006); Gille et al. (2011); Becker et al. (2013); Tymann et al. (2014). For the crystal structure of the corresponding trans-diastereomer, see: Tymann et al. (2015). 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).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); 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 50% probability level.

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

Crystal data top

C₁₇H₂₄N₂O₃S	D_x = 1.213 Mg m⁻³
M_r = 336.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3585 reflections
a = 9.4918 (7) Å	θ = 2.6–27.1°
b = 13.2348 (12) Å	µ = 0.19 mm⁻¹
c = 14.6691 (12) Å	T = 173 K
V = 1842.8 (3) Å³	Block, colourless
Z = 4	0.31 × 0.25 × 0.23 mm
F(000) = 720

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4215 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3526 reflections with I > 2σ(I)
Detector resolution: 16.0560 pixels mm^-1	R_int = 0.046
φ and ω scans	θ_max = 28.0°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −12→12
T_min = 0.98, T_max = 1.00	k = −15→16
15093 measured reflections	l = −19→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0401P)² + 0.1494P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4215 reflections	Δρ_max = 0.22 e Å⁻³
216 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Absolute structure: Flack x determined using 1277 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (4)

Crystal data top

C₁₇H₂₄N₂O₃S	V = 1842.8 (3) Å³
M_r = 336.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.4918 (7) Å	µ = 0.19 mm⁻¹
b = 13.2348 (12) Å	T = 173 K
c = 14.6691 (12) Å	0.31 × 0.25 × 0.23 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4215 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3526 reflections with I > 2σ(I)
T_min = 0.98, T_max = 1.00	R_int = 0.046
15093 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	Δρ_max = 0.22 e Å⁻³
S = 1.05	Δρ_min = −0.33 e Å⁻³
4215 reflections	Absolute structure: Flack x determined using 1277 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
216 parameters	Absolute structure parameter: −0.02 (4)
0 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

	x	y	z	U_iso*/U_eq
S	0.57466 (7)	0.53116 (6)	0.08855 (5)	0.02777 (17)
O1	0.45052 (19)	0.57619 (18)	0.05053 (14)	0.0389 (6)
O2	0.5837 (2)	0.42449 (16)	0.10068 (15)	0.0411 (5)
O3	1.1776 (2)	0.72234 (15)	−0.00066 (13)	0.0309 (5)
N1	0.6994 (2)	0.5647 (2)	0.01656 (15)	0.0241 (5)
N2	0.8352 (2)	0.53514 (19)	0.04375 (14)	0.0226 (5)
C1	0.7064 (4)	0.7294 (3)	0.4507 (2)	0.0510 (10)
H1A	0.6958	0.6789	0.4990	0.077*
H1B	0.6409	0.7854	0.4614	0.077*
H1C	0.8033	0.7550	0.4506	0.077*
C2	0.6745 (3)	0.6814 (2)	0.35949 (19)	0.0333 (7)
C3	0.7286 (3)	0.5861 (3)	0.3378 (2)	0.0358 (8)
H3	0.7880	0.5526	0.3803	0.043*
C4	0.6978 (3)	0.5398 (2)	0.25650 (18)	0.0308 (6)
H4	0.7341	0.4745	0.2433	0.037*
C5	0.6127 (3)	0.5896 (2)	0.19358 (18)	0.0259 (6)
C6	0.5606 (3)	0.6853 (2)	0.21212 (19)	0.0303 (7)
H6	0.5052	0.7199	0.1681	0.036*
C7	0.5902 (3)	0.7302 (2)	0.2954 (2)	0.0329 (7)
H7	0.5526	0.7950	0.3089	0.039*
C8	0.9350 (3)	0.5757 (2)	−0.00108 (18)	0.0240 (6)
H8	0.9128	0.6228	−0.0478	0.029*
C9	1.0880 (3)	0.5513 (2)	0.01786 (18)	0.0251 (6)
C10	1.1497 (3)	0.6526 (2)	0.05022 (18)	0.0227 (6)
C11	1.1652 (3)	0.6526 (2)	0.15308 (17)	0.0247 (6)
H11	1.2680	0.6440	0.1659	0.030*
C12	1.1208 (3)	0.7517 (2)	0.1995 (2)	0.0320 (7)
H12	1.1814	0.8067	0.1739	0.038*
C13	1.1488 (4)	0.7473 (3)	0.3020 (2)	0.0475 (9)
H13A	1.0847	0.6984	0.3302	0.071*
H13B	1.1332	0.8142	0.3288	0.071*
H13C	1.2464	0.7264	0.3127	0.071*
C14	0.9673 (3)	0.7800 (3)	0.1793 (2)	0.0416 (8)
H14A	0.9047	0.7275	0.2034	0.062*
H14B	0.9538	0.7858	0.1133	0.062*
H14C	0.9451	0.8448	0.2084	0.062*
C15	1.0931 (3)	0.5542 (2)	0.18366 (19)	0.0306 (7)
H15A	1.1406	0.5254	0.2379	0.037*
H15B	0.9927	0.5661	0.1984	0.037*
C16	1.1078 (3)	0.4835 (2)	0.1014 (2)	0.0304 (7)
H16A	1.2019	0.4512	0.1006	0.036*
H16B	1.0349	0.4300	0.1030	0.036*
C17	1.1573 (3)	0.5148 (2)	−0.0706 (2)	0.0359 (7)
H17A	1.2582	0.5039	−0.0602	0.054*
H17B	1.1447	0.5660	−0.1183	0.054*
H17C	1.1135	0.4513	−0.0900	0.054*
H1N	0.690 (3)	0.627 (3)	0.001 (2)	0.040 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0189 (3)	0.0290 (4)	0.0354 (4)	−0.0034 (3)	0.0053 (3)	−0.0060 (3)
O1	0.0171 (10)	0.0542 (15)	0.0455 (12)	0.0008 (10)	−0.0003 (9)	−0.0093 (11)
O2	0.0389 (11)	0.0293 (12)	0.0549 (14)	−0.0106 (10)	0.0121 (11)	−0.0049 (10)
O3	0.0323 (10)	0.0271 (12)	0.0334 (11)	−0.0043 (9)	0.0072 (9)	0.0008 (10)
N1	0.0182 (11)	0.0256 (14)	0.0286 (13)	0.0020 (10)	0.0006 (9)	−0.0015 (10)
N2	0.0177 (10)	0.0213 (12)	0.0286 (11)	0.0023 (10)	0.0013 (9)	−0.0062 (10)
C1	0.077 (3)	0.047 (2)	0.0290 (17)	−0.009 (2)	0.0018 (17)	0.0017 (16)
C2	0.0404 (17)	0.0341 (19)	0.0255 (15)	−0.0055 (15)	0.0097 (13)	0.0052 (12)
C3	0.0395 (17)	0.039 (2)	0.0291 (16)	0.0024 (15)	0.0036 (13)	0.0138 (14)
C4	0.0358 (15)	0.0263 (16)	0.0302 (15)	0.0065 (14)	0.0113 (12)	0.0071 (13)
C5	0.0204 (13)	0.0296 (17)	0.0278 (14)	−0.0006 (11)	0.0080 (11)	0.0012 (12)
C6	0.0249 (15)	0.0327 (17)	0.0334 (16)	0.0049 (14)	0.0025 (12)	−0.0005 (12)
C7	0.0352 (16)	0.0260 (17)	0.0375 (16)	0.0031 (14)	0.0084 (14)	−0.0025 (13)
C8	0.0219 (13)	0.0253 (15)	0.0247 (13)	−0.0015 (12)	0.0019 (11)	−0.0030 (11)
C9	0.0180 (12)	0.0243 (16)	0.0329 (14)	−0.0006 (12)	0.0038 (11)	−0.0059 (11)
C10	0.0126 (12)	0.0245 (16)	0.0310 (14)	0.0022 (11)	0.0036 (11)	−0.0035 (12)
C11	0.0159 (12)	0.0303 (17)	0.0279 (14)	0.0000 (12)	0.0005 (11)	−0.0016 (12)
C12	0.0323 (16)	0.0319 (18)	0.0319 (16)	−0.0016 (13)	0.0042 (12)	−0.0074 (13)
C13	0.054 (2)	0.057 (3)	0.0313 (17)	0.0063 (18)	0.0011 (16)	−0.0120 (16)
C14	0.0392 (18)	0.042 (2)	0.0434 (19)	0.0141 (16)	0.0068 (15)	−0.0046 (15)
C15	0.0272 (14)	0.0316 (17)	0.0330 (15)	0.0023 (13)	−0.0008 (12)	0.0076 (12)
C16	0.0210 (13)	0.0226 (16)	0.0475 (18)	0.0017 (11)	0.0010 (12)	0.0028 (13)
C17	0.0256 (14)	0.041 (2)	0.0417 (17)	−0.0039 (14)	0.0063 (13)	−0.0178 (14)

Geometric parameters (Å, º) top

S—O2	1.426 (2)	C9—C16	1.531 (4)
S—O1	1.433 (2)	C9—C17	1.534 (4)
S—N1	1.648 (2)	C9—C10	1.538 (4)
S—C5	1.761 (3)	C10—C11	1.516 (4)
O3—C10	1.216 (3)	C11—C12	1.537 (4)
N1—N2	1.405 (3)	C11—C15	1.539 (4)
N1—H1N	0.86 (3)	C11—H11	1.0000
N2—C8	1.272 (3)	C12—C13	1.528 (4)
C1—C2	1.511 (4)	C12—C14	1.533 (4)
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—C7	1.393 (4)	C13—H13C	0.9800
C2—C3	1.399 (5)	C14—H14A	0.9800
C3—C4	1.372 (4)	C14—H14B	0.9800
C3—H3	0.9500	C14—H14C	0.9800
C4—C5	1.392 (4)	C15—C16	1.533 (4)
C4—H4	0.9500	C15—H15A	0.9900
C5—C6	1.387 (4)	C15—H15B	0.9900
C6—C7	1.387 (4)	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—H7	0.9500	C17—H17A	0.9800
C8—C9	1.514 (3)	C17—H17B	0.9800
C8—H8	0.9500	C17—H17C	0.9800

O2—S—O1	120.65 (14)	O3—C10—C9	123.7 (2)
O2—S—N1	107.67 (13)	C11—C10—C9	110.1 (2)
O1—S—N1	103.26 (12)	C10—C11—C12	114.4 (2)
O2—S—C5	108.25 (14)	C10—C11—C15	104.3 (2)
O1—S—C5	109.04 (13)	C12—C11—C15	118.2 (2)
N1—S—C5	107.17 (12)	C10—C11—H11	106.4
N2—N1—S	113.73 (18)	C12—C11—H11	106.4
N2—N1—H1N	116 (2)	C15—C11—H11	106.4
S—N1—H1N	111 (2)	C13—C12—C14	111.3 (3)
C8—N2—N1	114.7 (2)	C13—C12—C11	110.8 (3)
C2—C1—H1A	109.5	C14—C12—C11	112.6 (3)
C2—C1—H1B	109.5	C13—C12—H12	107.3
H1A—C1—H1B	109.5	C14—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
C7—C2—C3	118.4 (3)	H13A—C13—H13B	109.5
C7—C2—C1	121.2 (3)	C12—C13—H13C	109.5
C3—C2—C1	120.5 (3)	H13A—C13—H13C	109.5
C4—C3—C2	121.5 (3)	H13B—C13—H13C	109.5
C4—C3—H3	119.3	C12—C14—H14A	109.5
C2—C3—H3	119.3	C12—C14—H14B	109.5
C3—C4—C5	119.2 (3)	H14A—C14—H14B	109.5
C3—C4—H4	120.4	C12—C14—H14C	109.5
C5—C4—H4	120.4	H14A—C14—H14C	109.5
C6—C5—C4	120.6 (3)	H14B—C14—H14C	109.5
C6—C5—S	120.0 (2)	C16—C15—C11	104.3 (2)
C4—C5—S	119.4 (2)	C16—C15—H15A	110.9
C5—C6—C7	119.5 (3)	C11—C15—H15A	110.9
C5—C6—H6	120.3	C16—C15—H15B	110.9
C7—C6—H6	120.3	C11—C15—H15B	110.9
C6—C7—C2	120.8 (3)	H15A—C15—H15B	108.9
C6—C7—H7	119.6	C9—C16—C15	105.1 (2)
C2—C7—H7	119.6	C9—C16—H16A	110.7
N2—C8—C9	122.0 (3)	C15—C16—H16A	110.7
N2—C8—H8	119.0	C9—C16—H16B	110.7
C9—C8—H8	119.0	C15—C16—H16B	110.7
C8—C9—C16	112.9 (2)	H16A—C16—H16B	108.8
C8—C9—C17	108.9 (2)	C9—C17—H17A	109.5
C16—C9—C17	116.1 (2)	C9—C17—H17B	109.5
C8—C9—C10	103.6 (2)	H17A—C17—H17B	109.5
C16—C9—C10	102.6 (2)	C9—C17—H17C	109.5
C17—C9—C10	111.9 (2)	H17A—C17—H17C	109.5
O3—C10—C11	126.2 (3)	H17B—C17—H17C	109.5

O2—S—N1—N2	−55.9 (2)	N2—C8—C9—C17	124.3 (3)
O1—S—N1—N2	175.41 (19)	N2—C8—C9—C10	−116.4 (3)
C5—S—N1—N2	60.3 (2)	C8—C9—C10—O3	−76.0 (3)
S—N1—N2—C8	−167.6 (2)	C16—C9—C10—O3	166.3 (2)
C7—C2—C3—C4	−1.5 (4)	C17—C9—C10—O3	41.2 (4)
C1—C2—C3—C4	178.1 (3)	C8—C9—C10—C11	102.3 (2)
C2—C3—C4—C5	1.1 (4)	C16—C9—C10—C11	−15.4 (3)
C3—C4—C5—C6	0.7 (4)	C17—C9—C10—C11	−140.5 (2)
C3—C4—C5—S	179.2 (2)	O3—C10—C11—C12	40.3 (4)
O2—S—C5—C6	−155.0 (2)	C9—C10—C11—C12	−137.9 (2)
O1—S—C5—C6	−22.0 (3)	O3—C10—C11—C15	171.0 (3)
N1—S—C5—C6	89.2 (2)	C9—C10—C11—C15	−7.3 (3)
O2—S—C5—C4	26.5 (2)	C10—C11—C12—C13	−176.4 (2)
O1—S—C5—C4	159.5 (2)	C15—C11—C12—C13	60.2 (3)
N1—S—C5—C4	−89.3 (2)	C10—C11—C12—C14	58.2 (3)
C4—C5—C6—C7	−2.1 (4)	C15—C11—C12—C14	−65.2 (3)
S—C5—C6—C7	179.4 (2)	C10—C11—C15—C16	27.2 (3)
C5—C6—C7—C2	1.7 (4)	C12—C11—C15—C16	155.5 (2)
C3—C2—C7—C6	0.0 (4)	C8—C9—C16—C15	−78.7 (3)
C1—C2—C7—C6	−179.6 (3)	C17—C9—C16—C15	154.5 (2)
N1—N2—C8—C9	−179.0 (2)	C10—C9—C16—C15	32.2 (2)
N2—C8—C9—C16	−6.2 (4)	C11—C15—C16—C9	−37.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86 (3)	2.00 (4)	2.836 (3)	164 (3)

Symmetry code: (i) x−1/2, −y+3/2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.86 (3)	2.00 (4)	2.836 (3)	164 (3)

Symmetry code: (i) x−1/2, −y+3/2, −z.

Acknowledgements

Financial support obtained from the Beilstein Institut is greatly acknowledged.

References

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Volume 71| Part 12| December 2015| Pages o904-o905

https://doi.org/10.1107/S2056989015020307

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

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