N-(2,6-Dimethyl-3-oxo-1-thia-4-aza­spiro­[4.5]dec-4-yl)-2-hydr­oxy-2,2-di­phenyl­acetamide

Yalçın, Ş.P.; Akkurt, M.; Şahin, E.; Güzel, Ö.; Salman, A.; İlhan, E.

doi:10.1107/S1600536808028651

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1919

doi:10.1107/S1600536808028651

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N-(2,6-Dimethyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2-hydroxy-2,2-diphenylacetamide

Şerife Pınar Yalçın,^a Mehmet Akkurt,^a ^* Ertan Şahin,^b Özlen Güzel,^c Aydın Salman ^c and Eser İhan ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Atatürk University, 22240 Erzurum, Turkey, and ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Istanbul, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 3 September 2008; accepted 7 September 2008; online 13 September 2008)

In the title compound, C₂₄H₂₈N₂O₃S, the pendant methyl C atom bonded to the cyclohexane ring is disordered over two sites in a 0.580 (11):0.420 (11) ratio. The cyclohexane ring adopts a distorted chair conformation while the thiazolidine ring has an envelope conformation. The two phenyl rings make a dihedral angle of 71.8 (2)° with each other. The conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal structure, an intermolecular hydrogen bond O—H⋯O occurs.

Related literature

For background, see: Güzel et al. (2006 ). For a related structure, see: Akkurt et al. (2007 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₈N₂O₃S
M_r = 423.55
Monoclinic, P 2₁ /c
a = 9.4942 (4) Å
b = 20.6765 (5) Å
c = 12.0052 (4) Å
β = 105.063 (2)°
V = 2275.73 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293.1 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS conversion diffractometer
Absorption correction: empirical (using intensity measurements)XABS2 (Parkin et al., 1995 ) T_min = 0.967, T_max = 0.967
6931 measured reflections
6931 independent reflections
3002 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.094
wR(F²) = 0.235
S = 1.05
6931 reflections
301 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—HO3⋯O1ⁱ	0.92 (5)	1.83 (5)	2.744 (4)	175 (5)
N2—HN2⋯O3	0.86 (3)	2.11 (3)	2.535 (4)	110 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028651/hb2789sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028651/hb2789Isup2.hkl

checkCIF report

Comment top

In our previous report (Güzel et al., 2006), we described the synthesis and evaluation of sixteen new2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamidederivatives, as potential antimicro-bacterial agents. We now report the crystal structure of the related title compound, (I), (Fig. 1).

The geometric parameters in (I) are comparable with those in 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide (Akkurt et al., 2007). The dihedral angle between the two phenyl rings (C13—C18) and (C19—C24) in (I) is 71.8 (2)°. The five-membered ring (S1/C2/C3/N1/C4) has an envelope conformation with S1 at the flap position [puckering parameters: Q₂ = 0.167 (3)Å and ϕ₂ = 352.2 (12)° (Cremer & Pople, 1975)]. The cyclohexane ring has a distorted chair conformation, with the puckering parameters: Q = 0.585 (7) Å, θ = 2.7 (7) and ϕ = 132 (14)°.

The molecular conformation and crystal packing are stabilized by N—H···O and O—H···O hydrogen bonding interactions (Table 1).

Related literature top

For background, see: Güzel et al. (2006). For a related structure, see: Akkurt et al. (2007). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 2-hydroxy-2,2-diphenylacetohydrazide (0.005 mol), 2-methylcyclohexanone (0.005 mol) and mercaptoacetic acid or α-mercaptopropionic acid (0.02 mol) was refluxed in 20 ml dry benzene for 5–6 h using a Dean-Stark water separator. Excess benzene was evaporated in vacuo. The resulting residue was triturated with saturated NaHCO₃ solution until CO₂ evolution ceased and was allowed to stand overnight or in some cases refrigerated until solidification. The solid thus obtained was washed with water, dried, and recrystallized from ethanol. [Yield 48%, mp 455–458 K]. IR(KBr) (ν, cm^-1): 3335 (O—H/N—H), 1679,1731 (C=O); ¹H-NMR (DMSO-d₆, 500 MHz) δ (p.p.m.): 0.93 (t, 3H, J = 6.83 Hz, 6-CH₃), 0.95–1.10 (m, 1H, spirodecane),1.11–1.14 (m, 1H, spirodecane), 1.19–1.27 (m, 1H, spirodecane),1.41 (t, 3H, J = 7.32 Hz, 2-CH₃), 1.45–1.67 (m, 5H, spirodecane), 1.83–1.87 (m, 1H, spirodecane), 3.77,3.85 (2q, 1H, J = 6.83 Hz, C₂—H), 6.78 (s, 1H, COH), 7.26–7.31 (m, 2H, Ar—H), 7.33–7.35 (m, 4H, Ar—H), 7.45–7.49 (m, 4H,Ar—H), 9.93,10.05 (2 s, 1H, CONH). Analysis calculated for C₂₄H₂₈N₂O₃S: C 67.90, H 6.65, N 6.60%. Found: C 68.27, H 6.89, N 6.24%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the molecular structure of (I) showing 10% displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. Packing for (I) with hydrogen bonds shown as dashed lines. The H atoms not involved in hydrogen contacts have been omitted.

N-(2,6-Dimethyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2-hydroxy-2,2- diphenylacetamide top

Crystal data top

C₂₄H₂₈N₂O₃S	F(000) = 900
M_r = 423.55	D_x = 1.236 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 4481 reflections
a = 9.4942 (4) Å	θ = 2.4–30.6°
b = 20.6765 (5) Å	µ = 0.17 mm⁻¹
c = 12.0052 (4) Å	T = 293 K
β = 105.063 (2)°	Block, pale yellow
V = 2275.73 (14) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS conversion diffractometer	6931 independent reflections
Radiation source: Sealed Tube	3002 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.000
Detector resolution: 10.0000 pixels mm^-1	θ_max = 30.5°, θ_min = 2.6°
dtprofit.ref scans	h = −13→13
Absorption correction: empirical (using intensity measurements) (using intensity measurements) XABS2 (Parkin et al., 1995)	k = 0→29
T_min = 0.967, T_max = 0.967	l = 0→17
6931 measured reflections

Refinement top

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)] = 0.094	Hydrogen site location: difmap and geom
wR(F²) = 0.235	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0588P)² + 1.0272P] where P = (F_o² + 2F_c²)/3
6931 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₂₈N₂O₃S	V = 2275.73 (14) Å³
M_r = 423.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4942 (4) Å	µ = 0.17 mm⁻¹
b = 20.6765 (5) Å	T = 293 K
c = 12.0052 (4) Å	0.20 × 0.20 × 0.20 mm
β = 105.063 (2)°

Data collection top

Rigaku R-AXIS conversion diffractometer	6931 independent reflections
Absorption correction: empirical (using intensity measurements) (using intensity measurements) XABS2 (Parkin et al., 1995)	3002 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.967	R_int = 0.000
6931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.094	0 restraints
wR(F²) = 0.235	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.28 e Å⁻³
6931 reflections	Δρ_min = −0.35 e Å⁻³
301 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	Occ. (<1)
S1	−0.11370 (14)	0.07379 (6)	0.21004 (13)	0.1429 (6)
O1	0.1607 (3)	−0.03247 (12)	0.4220 (2)	0.0880 (10)
O2	0.2399 (2)	0.11034 (14)	0.5737 (2)	0.0862 (9)
O3	0.5610 (3)	0.07766 (12)	0.48919 (19)	0.0738 (9)
N1	0.1428 (3)	0.06961 (14)	0.3499 (2)	0.0709 (10)
N2	0.2874 (3)	0.08385 (15)	0.4045 (2)	0.0713 (10)
C1	−0.0926 (4)	−0.0586 (2)	0.2264 (4)	0.0989 (17)
C2	−0.0673 (3)	0.00255 (17)	0.2971 (3)	0.0772 (11)
C3	0.0903 (3)	0.01066 (18)	0.3637 (3)	0.0698 (11)
C4	0.0490 (4)	0.11999 (18)	0.2824 (3)	0.0791 (12)
C5	0.1203 (7)	0.1502 (3)	0.1956 (4)	0.109 (2)
C6A	0.1402 (11)	0.1054 (5)	0.1149 (8)	0.109 (4)	0.580 (11)
C7	0.0264 (9)	0.2027 (3)	0.1258 (6)	0.188 (4)
C8	0.0013 (10)	0.2558 (4)	0.2017 (8)	0.212 (5)
C9	−0.0740 (7)	0.2280 (3)	0.2883 (7)	0.170 (3)
C10	0.0158 (6)	0.1737 (3)	0.3578 (6)	0.106 (2)
C11	0.3265 (3)	0.09945 (16)	0.5184 (3)	0.0671 (11)
C12	0.4926 (3)	0.10928 (16)	0.5668 (3)	0.0630 (10)
C13	0.5154 (3)	0.18202 (17)	0.5640 (3)	0.0689 (11)
C14	0.5762 (5)	0.2092 (2)	0.4832 (3)	0.0970 (17)
C15	0.5908 (6)	0.2758 (3)	0.4764 (4)	0.123 (3)
C16	0.5463 (6)	0.3152 (2)	0.5502 (5)	0.122 (2)
C17	0.4866 (5)	0.2891 (2)	0.6331 (5)	0.115 (2)
C18	0.4700 (4)	0.2227 (2)	0.6395 (4)	0.0906 (17)
C19	0.5443 (3)	0.07960 (16)	0.6865 (3)	0.0636 (11)
C20	0.6706 (4)	0.10250 (19)	0.7626 (3)	0.0812 (14)
C21	0.7222 (5)	0.0740 (3)	0.8703 (3)	0.1008 (18)
C22	0.6495 (6)	0.0232 (3)	0.9013 (4)	0.111 (2)
C23	0.5267 (5)	−0.0006 (2)	0.8266 (4)	0.1013 (17)
C24	0.4747 (4)	0.02714 (19)	0.7194 (3)	0.0827 (14)
C6B	−0.0810 (13)	0.1490 (6)	0.4150 (10)	0.092 (4)	0.420 (11)
HO3	0.656 (5)	0.065 (2)	0.521 (4)	0.117 (15)*
H1A	−0.19400	−0.06190	0.18650	0.1480*
H1C	−0.03520	−0.05760	0.17130	0.1480*
H2	−0.12760	0.00110	0.35200	0.0920*
H1B	−0.06470	−0.09530	0.27630	0.1480*
H6A1	0.19960	0.07040	0.15370	0.1640*	0.580 (11)
H6A2	0.18750	0.12590	0.06270	0.1640*	0.580 (11)
H6A3	0.04710	0.08890	0.07260	0.1640*	0.580 (11)
H7A	0.07390	0.21990	0.06970	0.2260*
H7B	−0.06660	0.18450	0.08420	0.2260*
H8A	−0.05930	0.28900	0.15580	0.2550*
HN2	0.353 (3)	0.0683 (14)	0.374 (3)	0.060 (10)*
H9A	−0.16920	0.21150	0.24780	0.2030*
H9B	−0.08800	0.26190	0.34010	0.2030*
H10A	0.115 (6)	0.193 (2)	0.400 (4)	0.0500*	0.580 (11)
H10B	−0.010 (8)	0.156 (4)	0.410 (6)	0.0500*	0.580 (11)
H14	0.60820	0.18270	0.43220	0.1160*
H15	0.63160	0.29340	0.42060	0.1470*
H16	0.55580	0.35980	0.54500	0.1460*
H17	0.45730	0.31610	0.68490	0.1380*
H18	0.42810	0.20530	0.69490	0.1090*
H20	0.72090	0.13700	0.74150	0.0970*
H21	0.80650	0.08960	0.92130	0.1210*
H22	0.68370	0.00460	0.97380	0.1320*
H23	0.47800	−0.03560	0.84810	0.1210*
H24	0.39170	0.01030	0.66850	0.0990*
H8B	0.09360	0.27520	0.24180	0.2550*
H5A	0.229 (7)	0.170 (3)	0.247 (5)	0.0500*	0.420 (11)
H5B	0.175 (9)	0.122 (5)	0.171 (9)	0.0500*	0.420 (11)
H6B1	−0.10350	0.18160	0.46470	0.1380*	0.420 (11)
H6B2	−0.03800	0.11230	0.46020	0.1380*	0.420 (11)
H6B3	−0.16890	0.13590	0.35980	0.1380*	0.420 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1011 (9)	0.1045 (9)	0.1652 (13)	−0.0240 (7)	−0.0691 (8)	0.0456 (8)
O1	0.0723 (15)	0.0910 (18)	0.0904 (18)	0.0132 (13)	0.0026 (13)	0.0235 (14)
O2	0.0574 (13)	0.126 (2)	0.0696 (15)	0.0027 (14)	0.0067 (12)	0.0014 (14)
O3	0.0580 (13)	0.0954 (18)	0.0620 (14)	0.0095 (12)	0.0050 (11)	−0.0062 (12)
N1	0.0575 (15)	0.0745 (18)	0.0670 (17)	−0.0033 (13)	−0.0084 (12)	0.0063 (14)
N2	0.0517 (15)	0.095 (2)	0.0589 (17)	−0.0003 (15)	−0.0007 (13)	−0.0060 (15)
C1	0.089 (3)	0.100 (3)	0.098 (3)	−0.013 (2)	0.007 (2)	−0.015 (2)
C2	0.0580 (19)	0.081 (2)	0.084 (2)	−0.0039 (17)	0.0028 (16)	−0.0012 (19)
C3	0.0591 (19)	0.080 (2)	0.063 (2)	0.0074 (17)	0.0028 (15)	0.0009 (17)
C4	0.065 (2)	0.078 (2)	0.078 (2)	−0.0025 (18)	−0.0107 (17)	0.0153 (19)
C5	0.132 (4)	0.104 (4)	0.079 (3)	−0.007 (3)	0.005 (3)	0.019 (3)
C6A	0.106 (6)	0.139 (8)	0.082 (6)	0.030 (5)	0.023 (5)	−0.006 (5)
C7	0.239 (8)	0.132 (5)	0.135 (5)	−0.041 (5)	−0.056 (5)	0.063 (4)
C8	0.227 (9)	0.107 (5)	0.225 (9)	−0.023 (5)	−0.081 (7)	0.060 (6)
C9	0.136 (5)	0.098 (4)	0.218 (7)	0.037 (4)	−0.056 (5)	−0.016 (4)
C10	0.085 (3)	0.088 (3)	0.129 (5)	0.016 (3)	0.002 (3)	0.009 (3)
C11	0.0555 (18)	0.075 (2)	0.064 (2)	0.0002 (15)	0.0035 (15)	0.0074 (16)
C12	0.0567 (17)	0.075 (2)	0.0529 (17)	0.0009 (15)	0.0063 (14)	0.0008 (15)
C13	0.0609 (19)	0.074 (2)	0.065 (2)	0.0010 (16)	0.0040 (15)	−0.0002 (17)
C14	0.116 (3)	0.093 (3)	0.080 (3)	−0.022 (2)	0.022 (2)	0.001 (2)
C15	0.162 (5)	0.101 (4)	0.101 (4)	−0.033 (3)	0.027 (3)	0.009 (3)
C16	0.139 (4)	0.079 (3)	0.135 (5)	−0.014 (3)	0.012 (4)	0.004 (3)
C17	0.115 (4)	0.089 (3)	0.136 (4)	0.004 (3)	0.025 (3)	−0.023 (3)
C18	0.084 (3)	0.084 (3)	0.104 (3)	0.003 (2)	0.025 (2)	−0.007 (2)
C19	0.0625 (18)	0.074 (2)	0.0508 (17)	0.0061 (16)	0.0085 (14)	−0.0003 (15)
C20	0.075 (2)	0.097 (3)	0.060 (2)	−0.0005 (19)	−0.0035 (17)	−0.0072 (18)
C21	0.091 (3)	0.132 (4)	0.061 (2)	0.016 (3)	−0.013 (2)	−0.008 (2)
C22	0.122 (4)	0.136 (4)	0.065 (3)	0.036 (3)	0.009 (3)	0.022 (3)
C23	0.107 (3)	0.107 (3)	0.087 (3)	0.014 (3)	0.020 (3)	0.029 (2)
C24	0.077 (2)	0.089 (3)	0.076 (2)	0.007 (2)	0.0089 (18)	0.010 (2)
C6B	0.070 (7)	0.101 (8)	0.107 (8)	0.002 (6)	0.025 (6)	−0.021 (6)

Geometric parameters (Å, º) top

S1—C2	1.794 (4)	C21—C22	1.361 (8)
S1—C4	1.832 (4)	C22—C23	1.365 (7)
O1—C3	1.220 (4)	C23—C24	1.378 (6)
O2—C11	1.205 (4)	C1—H1A	0.9600
O3—C12	1.425 (4)	C1—H1B	0.9600
O3—HO3	0.92 (5)	C1—H1C	0.9600
N1—C3	1.343 (5)	C2—H2	0.9800
N1—C4	1.470 (5)	C5—H5A	1.13 (7)
N1—N2	1.391 (4)	C5—H5B	0.88 (9)
N2—C11	1.359 (4)	C6A—H6A1	0.9600
N2—HN2	0.86 (3)	C6A—H6A2	0.9600
C1—C2	1.507 (6)	C6A—H6A3	0.9600
C2—C3	1.511 (4)	C6B—H6B1	0.9600
C4—C5	1.517 (7)	C6B—H6B2	0.9600
C4—C10	1.517 (7)	C6B—H6B3	0.9600
C5—C7	1.512 (9)	C7—H7A	0.9700
C5—C6A	1.388 (11)	C7—H7B	0.9700
C6B—C10	1.380 (14)	C8—H8A	0.9700
C7—C8	1.485 (11)	C8—H8B	0.9700
C8—C9	1.519 (12)	C9—H9B	0.9700
C9—C10	1.521 (9)	C9—H9A	0.9700
C11—C12	1.546 (4)	C10—H10B	0.82 (7)
C12—C19	1.522 (5)	C10—H10A	1.03 (5)
C12—C13	1.521 (5)	C14—H14	0.9300
C13—C18	1.385 (5)	C15—H15	0.9300
C13—C14	1.372 (5)	C16—H16	0.9300
C14—C15	1.389 (7)	C17—H17	0.9300
C15—C16	1.350 (8)	C18—H18	0.9300
C16—C17	1.377 (8)	C20—H20	0.9300
C17—C18	1.386 (6)	C21—H21	0.9300
C19—C24	1.380 (5)	C22—H22	0.9300
C19—C20	1.388 (5)	C23—H23	0.9300
C20—C21	1.389 (5)	C24—H24	0.9300

C2—S1—C4	95.90 (17)	S1—C2—H2	109.00
C12—O3—HO3	115 (3)	C1—C2—H2	109.00
N2—N1—C3	119.1 (3)	C3—C2—H2	109.00
C3—N1—C4	121.3 (3)	C4—C5—H5A	106 (3)
N2—N1—C4	119.5 (3)	C4—C5—H5B	111 (7)
N1—N2—C11	120.2 (3)	C7—C5—H5A	111 (3)
N1—N2—HN2	117 (2)	C7—C5—H5B	127 (7)
C11—N2—HN2	119 (2)	H5A—C5—H5B	84 (7)
C1—C2—C3	112.5 (3)	C5—C6A—H6A1	109.00
S1—C2—C1	112.5 (3)	C5—C6A—H6A2	109.00
S1—C2—C3	106.1 (2)	C5—C6A—H6A3	109.00
O1—C3—C2	122.8 (3)	H6A1—C6A—H6A2	110.00
O1—C3—N1	124.6 (3)	H6A1—C6A—H6A3	109.00
N1—C3—C2	112.6 (3)	H6A2—C6A—H6A3	110.00
S1—C4—N1	102.0 (2)	H6B2—C6B—H6B3	109.00
S1—C4—C5	111.2 (3)	C10—C6B—H6B3	109.00
C5—C4—C10	107.9 (4)	C10—C6B—H6B1	109.00
S1—C4—C10	112.6 (3)	C10—C6B—H6B2	109.00
N1—C4—C5	110.9 (4)	H6B1—C6B—H6B2	110.00
N1—C4—C10	112.3 (3)	H6B1—C6B—H6B3	109.00
C4—C5—C6A	111.8 (6)	C5—C7—H7B	109.00
C4—C5—C7	111.9 (5)	C5—C7—H7A	110.00
C6A—C5—C7	105.1 (6)	H7A—C7—H7B	108.00
C5—C7—C8	110.9 (6)	C8—C7—H7A	109.00
C7—C8—C9	108.6 (6)	C8—C7—H7B	109.00
C8—C9—C10	111.0 (6)	C9—C8—H8B	110.00
C6B—C10—C9	101.3 (7)	C7—C8—H8A	110.00
C4—C10—C6B	107.1 (7)	C7—C8—H8B	110.00
C4—C10—C9	112.8 (5)	C9—C8—H8A	110.00
O2—C11—N2	123.5 (3)	H8A—C8—H8B	108.00
O2—C11—C12	123.0 (3)	C8—C9—H9A	109.00
N2—C11—C12	113.2 (3)	C8—C9—H9B	109.00
C11—C12—C13	105.0 (3)	H9A—C9—H9B	108.00
C11—C12—C19	110.4 (3)	C10—C9—H9B	109.00
C13—C12—C19	114.0 (3)	C10—C9—H9A	109.00
O3—C12—C19	110.0 (3)	C9—C10—H10A	107 (2)
O3—C12—C11	106.7 (3)	C4—C10—H10B	106 (6)
O3—C12—C13	110.3 (3)	C4—C10—H10A	106 (3)
C12—C13—C14	120.6 (3)	C9—C10—H10B	121 (6)
C14—C13—C18	118.3 (3)	H10A—C10—H10B	102 (6)
C12—C13—C18	121.1 (3)	C13—C14—H14	120.00
C13—C14—C15	121.0 (4)	C15—C14—H14	119.00
C14—C15—C16	120.5 (5)	C16—C15—H15	120.00
C15—C16—C17	119.7 (4)	C14—C15—H15	120.00
C16—C17—C18	120.2 (4)	C15—C16—H16	120.00
C13—C18—C17	120.4 (4)	C17—C16—H16	120.00
C12—C19—C20	119.7 (3)	C16—C17—H17	120.00
C12—C19—C24	121.8 (3)	C18—C17—H17	120.00
C20—C19—C24	118.4 (3)	C17—C18—H18	120.00
C19—C20—C21	120.2 (4)	C13—C18—H18	120.00
C20—C21—C22	120.1 (4)	C19—C20—H20	120.00
C21—C22—C23	120.4 (4)	C21—C20—H20	120.00
C22—C23—C24	120.1 (4)	C20—C21—H21	120.00
C19—C24—C23	120.8 (4)	C22—C21—H21	120.00
C2—C1—H1A	109.00	C23—C22—H22	120.00
C2—C1—H1B	110.00	C21—C22—H22	120.00
C2—C1—H1C	110.00	C22—C23—H23	120.00
H1A—C1—H1B	109.00	C24—C23—H23	120.00
H1A—C1—H1C	109.00	C23—C24—H24	120.00
H1B—C1—H1C	109.00	C19—C24—H24	120.00

C4—S1—C2—C1	−135.6 (3)	C8—C9—C10—C4	−56.3 (7)
C4—S1—C2—C3	−12.3 (3)	O2—C11—C12—O3	166.6 (3)
C2—S1—C4—N1	13.4 (2)	O2—C11—C12—C13	−76.3 (4)
C2—S1—C4—C5	131.6 (3)	O2—C11—C12—C19	47.0 (4)
C2—S1—C4—C10	−107.2 (4)	N2—C11—C12—O3	−19.8 (4)
C3—N1—N2—C11	−79.3 (4)	N2—C11—C12—C13	97.4 (3)
C4—N1—N2—C11	98.2 (4)	N2—C11—C12—C19	−139.3 (3)
N2—N1—C3—O1	0.3 (5)	O3—C12—C13—C14	8.4 (4)
N2—N1—C3—C2	−178.9 (3)	O3—C12—C13—C18	−174.3 (3)
C4—N1—C3—O1	−177.2 (3)	C11—C12—C13—C14	−106.2 (4)
C4—N1—C3—C2	3.7 (4)	C11—C12—C13—C18	71.1 (4)
N2—N1—C4—S1	170.4 (2)	C19—C12—C13—C14	132.8 (3)
N2—N1—C4—C5	52.0 (4)	C19—C12—C13—C18	−49.9 (4)
N2—N1—C4—C10	−68.8 (4)	O3—C12—C19—C20	86.8 (4)
C3—N1—C4—S1	−12.2 (4)	O3—C12—C19—C24	−88.6 (4)
C3—N1—C4—C5	−130.6 (4)	C11—C12—C19—C20	−155.6 (3)
C3—N1—C4—C10	108.6 (4)	C11—C12—C19—C24	29.0 (4)
N1—N2—C11—O2	−10.3 (5)	C13—C12—C19—C20	−37.7 (4)
N1—N2—C11—C12	176.1 (3)	C13—C12—C19—C24	146.9 (3)
S1—C2—C3—O1	−171.9 (3)	C12—C13—C14—C15	176.8 (4)
S1—C2—C3—N1	7.3 (3)	C18—C13—C14—C15	−0.6 (6)
C1—C2—C3—O1	−48.6 (5)	C12—C13—C18—C17	−177.6 (4)
C1—C2—C3—N1	130.6 (3)	C14—C13—C18—C17	−0.2 (6)
S1—C4—C5—C6A	−49.6 (7)	C13—C14—C15—C16	0.6 (8)
S1—C4—C5—C7	67.9 (5)	C14—C15—C16—C17	0.3 (8)
N1—C4—C5—C6A	63.1 (7)	C15—C16—C17—C18	−1.1 (8)
N1—C4—C5—C7	−179.5 (4)	C16—C17—C18—C13	1.1 (7)
C10—C4—C5—C6A	−173.5 (6)	C12—C19—C20—C21	−177.3 (4)
C10—C4—C5—C7	−56.0 (6)	C24—C19—C20—C21	−1.8 (6)
S1—C4—C10—C9	−68.8 (5)	C12—C19—C24—C23	177.4 (4)
N1—C4—C10—C9	176.7 (4)	C20—C19—C24—C23	2.0 (6)
C5—C4—C10—C9	54.2 (6)	C19—C20—C21—C22	0.4 (7)
C4—C5—C7—C8	61.0 (8)	C20—C21—C22—C23	0.8 (8)
C6A—C5—C7—C8	−177.6 (8)	C21—C22—C23—C24	−0.6 (8)
C5—C7—C8—C9	−59.5 (9)	C22—C23—C24—C19	−0.8 (7)
C7—C8—C9—C10	57.2 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O1ⁱ	0.92 (5)	1.83 (5)	2.744 (4)	175 (5)
N2—HN2···O3	0.86 (3)	2.11 (3)	2.535 (4)	110 (3)
C6A—H6A1···N1	0.96	2.55	2.911 (10)	102
C6A—H6A3···S1	0.96	2.54	2.996 (11)	109
C7—H7B···S1	0.97	2.84	3.255 (7)	107
C14—H14···O3	0.93	2.35	2.726 (5)	103

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈N₂O₃S
M_r	423.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.4942 (4), 20.6765 (5), 12.0052 (4)
β (°)	105.063 (2)
V (Å³)	2275.73 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS conversion diffractometer
Absorption correction	Empirical (using intensity measurements) (using intensity measurements) XABS2 (Parkin et al., 1995)
T_min, T_max	0.967, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	6931, 6931, 3002
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.094, 0.235, 1.05
No. of reflections	6931
No. of parameters	301
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.35

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O1ⁱ	0.92 (5)	1.83 (5)	2.744 (4)	175 (5)
N2—HN2···O3	0.86 (3)	2.11 (3)	2.535 (4)	110 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors are indebted to the Department of Chemistry, Atatüurk University, Erzurum, Turkey, for the use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund.

References

Akkurt, M., Karaca, S., Şahin, E., Güzel, Ö., Salman, A. & İlhan, E. (2007). Acta Cryst. E63, o3379–o3380. Web of Science CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Güzel, Ö., İlhan, E. & Salman, A. (2006). Monatsh. Chem. 137, 795–801. Google Scholar
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1919

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

N-(2,6-Di­methyl-3-oxo-1-thia-4-aza­spiro­[4.5]dec-4-yl)-2-hydr­­oxy-2,2-di­phenyl­acetamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2,6-Dimethyl-3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2-hydroxy-2,2-diphenylacetamide