3-Isopropyl-1-{2-[(1-methyl-1H-tetra­zol-5-yl)sulfan­yl]acet­yl}-2,6-di­phenyl­piperidin-4-one hemihydrate

Ganesan, S.; Sugumar, P.; Ananthan, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536813026500

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1598

doi:10.1107/S1600536813026500

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3-Isopropyl-1-{2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetyl}-2,6-diphenylpiperidin-4-one hemihydrate

S. Ganesan,^a,^b P. Sugumar,^c S. Ananthan ^b and M. N. Ponnuswamy ^c ^*

^aResearch Development Centre, Orchid Chemicals and Pharmaceuticals Ltd, Sozhinganallur, Chennai 600 119, India, ^bDepartment of Chemistry, Presidency College (Autonomous), Chennai 600 005, India, and ^cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 4 September 2013; accepted 25 September 2013; online 2 October 2013)

In the title compound, C₂₄H₂₇N₅O₂S·0.5H₂O, the piperidine ring adopts a distorted boat conformation. The phenyl rings subtend dihedral angles of 69.7 (1) and 88.7 (1)° with the best plane through the piperidine moiety. In the crystal, symmetry-related molecules are linked through a network of C—H⋯O and C—H⋯N interactions, the former connecting them into zigzag chains along the c-axis direction and the latter forming an R²₂(4)motif. The dimer formation (C—H⋯N) and the repetition of symmetry-related molecules (C—H⋯O) along the b-axis direction stabilize the packing mode. The water molecule is located on a twofold rotation axis.

CCDC reference: 963167

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₂₇N₅O₂S·0.5H₂O
M_r = 458.57
Monoclinic, C 2/c
a = 28.7522 (9) Å
b = 11.1809 (4) Å
c = 16.5584 (5) Å
β = 115.303 (2)°
V = 4812.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.22 × 0.19 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.964, T_max = 0.972
22058 measured reflections
6013 independent reflections
4157 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.146
S = 1.04
6013 reflections
297 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25C⋯O1ⁱ	0.96	2.47	3.406 (3)	166
C18—H18⋯O1ⁱⁱ	0.93	2.54	3.312 (2)	140
C25—H25B⋯N4ⁱⁱⁱ	0.96	2.54	3.472 (3)	165
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 963167

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813026500/bt6930sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026500/bt6930Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026500/bt6930Isup3.cml

checkCIF report

Comment top

In a way to find piperidin-4-one based lead drug molecules for the antimicrobial therapy, various piperidin-4-ones were prepared by condensing N-chloroacetyl-2,6-diphenylpiperidin-4-one with 5-mercapto-(1-methyltetrazole) (Aridoss et al., 2009). 5-Mercapto-(1-methyl tetrazole) is the active part of a number of cephalosporanic drugs like Cefamandole, Cefoperazone, Cefmetazole sodium & Cefotetan and responsible for its activity. The present investigation was undertaken to establish the structure and conformation of the title compound by X-ray crystallographic methods.

The ORTEP plot of the molecule is shown in Fig. 1. The piperidine ring adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983): q₂=0.662 (2) Å, q₃ = 0.079 (2) Å, ϕ₂ = 76.86 (2)° and Δ_s(N1 & C4)= 74.11 (2)°.

The methyltetrazol ring is planar with the maximum deviation -0.003 (2) Å for N4 atom. The endocyclic bond lengths of N2–N3=1.362 (4)°, N3–N4= 1.278 (4) Å & N4–N5 = 1.348 (3) Å, clearly indicate that they are alternate single and double bonds.

The carbonyl group is almost anti-periplanar to C2 and C6, [C2—C3—C4—O1 = 155.9 (2)°; C6—C5—C4—O1= 151.1 (2)°]. The dihedral angles between the best plane through the piperidine ring and the phenyl rings are 69.7 (1)° & 88.7 (1)°. The two phenyl rings are oriented to each other with a dihedral angle of 70.5 (1)°.

Symmetry related molecules are linked through a network of intermolecular C—H···O and C—H···N interactions. C18–H18···O1 and C25–H25B···O1 connect the molecules to zigzag chains. Another motif R²₂(4), involving the weak interaction C25—H25A···N4 is shown in Fig. 2 (Bernstein et al., 1995).

Related literature top

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To anhydrous DMF(10 ml), N-Chloroacetyl-3-isopropyl-2,6-diphenylpiperidin-4-one (1 mole), 5-Mercapto-1-methyltetrazole(1 mole) followed by potassium carbonate (1.5 mole) was added and stirred for 1 hr at room temperature. The reaction mass was heated to 60°C and stirred and monitored using TLC. After completion of reaction, the reaction mass was quenched into water and the product was extracted with dichloromethane. The dichloromethane layer distilled completely and to the residue methanol was added and kept in overnight. The solid obtained was filtered and dried at 60° C under vacuum. Single crystals were obtained by re-crystallization using ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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 atomic numbering and displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed down c axis.

3-Isopropyl-1-{2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetyl}-2,6-diphenylpiperidin-4-one hemihydrate top

Crystal data top

C₂₄H₂₇N₅O₂S·0.5H₂O	F(000) = 1944
M_r = 458.57	D_x = 1.266 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4157 reflections
a = 28.7522 (9) Å	θ = 2.5–28.5°
b = 11.1809 (4) Å	µ = 0.17 mm⁻¹
c = 16.5584 (5) Å	T = 293 K
β = 115.303 (2)°	Block, white crystalline
V = 4812.4 (3) Å³	0.22 × 0.19 × 0.17 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	6013 independent reflections
Radiation source: fine-focus sealed tube	4157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −38→37
T_min = 0.964, T_max = 0.972	k = −14→14
22058 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0657P)² + 3.1292P] where P = (F_o² + 2F_c²)/3
6013 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₄H₂₇N₅O₂S·0.5H₂O	V = 4812.4 (3) Å³
M_r = 458.57	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.7522 (9) Å	µ = 0.17 mm⁻¹
b = 11.1809 (4) Å	T = 293 K
c = 16.5584 (5) Å	0.22 × 0.19 × 0.17 mm
β = 115.303 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6013 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4157 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.972	R_int = 0.026
22058 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
6013 reflections	Δρ_min = −0.25 e Å⁻³
297 parameters

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
C2	0.36794 (6)	0.31060 (16)	0.37251 (12)	0.0412 (4)
H2	0.3603	0.2457	0.3289	0.049*
C3	0.40052 (7)	0.40262 (18)	0.35071 (12)	0.0492 (4)
H3	0.4339	0.3659	0.3635	0.059*
C4	0.41000 (7)	0.51029 (18)	0.41040 (13)	0.0519 (5)
C5	0.37256 (7)	0.52979 (16)	0.45051 (12)	0.0465 (4)
H5A	0.3715	0.6147	0.4617	0.056*
H5B	0.3856	0.4894	0.5078	0.056*
C6	0.31739 (6)	0.48676 (14)	0.39456 (11)	0.0388 (4)
H6	0.3012	0.5417	0.3441	0.047*
C7	0.28781 (6)	0.49375 (15)	0.45121 (11)	0.0402 (4)
C8	0.25431 (7)	0.58770 (17)	0.43993 (14)	0.0519 (5)
H8	0.2485	0.6437	0.3951	0.062*
C9	0.22951 (9)	0.5988 (2)	0.49479 (18)	0.0661 (6)
H9	0.2071	0.6625	0.4868	0.079*
C10	0.23757 (9)	0.5170 (2)	0.56082 (17)	0.0682 (6)
H10	0.2211	0.5253	0.5981	0.082*
C11	0.27031 (9)	0.4222 (2)	0.57168 (15)	0.0638 (6)
H11	0.2755	0.3657	0.6159	0.077*
C12	0.29535 (8)	0.41052 (17)	0.51762 (13)	0.0508 (4)
H12	0.3175	0.3464	0.5257	0.061*
C13	0.39463 (6)	0.25381 (16)	0.46536 (12)	0.0439 (4)
C14	0.36763 (7)	0.16991 (17)	0.48954 (14)	0.0525 (5)
H14	0.3345	0.1489	0.4490	0.063*
C15	0.38885 (9)	0.1164 (2)	0.57293 (15)	0.0640 (6)
H15	0.3698	0.0611	0.5883	0.077*
C16	0.43792 (9)	0.1451 (2)	0.63289 (16)	0.0708 (6)
H16	0.4522	0.1097	0.6891	0.085*
C17	0.46572 (8)	0.2261 (2)	0.60943 (16)	0.0712 (7)
H17	0.4991	0.2450	0.6498	0.085*
C18	0.44445 (7)	0.28039 (19)	0.52588 (14)	0.0570 (5)
H18	0.4638	0.3349	0.5106	0.068*
C19	0.37600 (8)	0.4421 (2)	0.25143 (14)	0.0598 (5)
H19	0.3441	0.4849	0.2402	0.072*
C20	0.36228 (12)	0.3358 (3)	0.18807 (16)	0.0836 (8)
H20A	0.3481	0.3639	0.1275	0.125*
H20B	0.3374	0.2867	0.1968	0.125*
H20C	0.3927	0.2896	0.2000	0.125*
C21	0.41134 (12)	0.5283 (3)	0.2321 (2)	0.1060 (11)
H21A	0.4432	0.4888	0.2434	0.159*
H21B	0.4181	0.5971	0.2701	0.159*
H21C	0.3950	0.5530	0.1707	0.159*
C22	0.27371 (6)	0.31101 (15)	0.30215 (11)	0.0386 (4)
C23	0.22425 (6)	0.37998 (17)	0.27937 (12)	0.0456 (4)
H23A	0.2283	0.4620	0.2643	0.055*
H23B	0.2159	0.3808	0.3303	0.055*
C24	0.12585 (7)	0.41117 (17)	0.17409 (13)	0.0499 (4)
C25	0.06530 (10)	0.3638 (2)	0.01369 (17)	0.0818 (8)
H25A	0.0921	0.3667	−0.0062	0.123*
H25B	0.0352	0.4030	−0.0292	0.123*
H25C	0.0573	0.2819	0.0199	0.123*
N1	0.31787 (5)	0.36569 (12)	0.35824 (9)	0.0368 (3)
N2	0.12550 (7)	0.48754 (19)	0.23410 (14)	0.0695 (5)
N3	0.08016 (8)	0.5478 (2)	0.19371 (18)	0.0833 (6)
N4	0.05421 (7)	0.51015 (18)	0.11397 (18)	0.0799 (6)
N5	0.08241 (6)	0.42381 (15)	0.09937 (12)	0.0600 (5)
O1	0.44618 (6)	0.57684 (16)	0.42809 (13)	0.0792 (5)
O2	0.27217 (5)	0.21064 (12)	0.27106 (9)	0.0508 (3)
S1	0.173492 (17)	0.30767 (4)	0.18556 (3)	0.04999 (15)
O1W	0.0000	0.7061 (7)	0.2500	0.373 (7)
H1W	0.0172	0.6692	0.2298	0.560*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0302 (8)	0.0449 (9)	0.0444 (9)	−0.0009 (7)	0.0121 (7)	−0.0003 (7)
C3	0.0349 (9)	0.0609 (12)	0.0488 (10)	−0.0035 (8)	0.0152 (8)	0.0055 (8)
C4	0.0369 (9)	0.0564 (11)	0.0538 (11)	−0.0119 (8)	0.0110 (8)	0.0054 (8)
C5	0.0403 (9)	0.0427 (9)	0.0481 (9)	−0.0116 (7)	0.0109 (8)	−0.0033 (7)
C6	0.0345 (8)	0.0355 (8)	0.0397 (8)	−0.0034 (6)	0.0093 (7)	0.0020 (6)
C7	0.0379 (8)	0.0378 (9)	0.0405 (8)	−0.0080 (7)	0.0125 (7)	−0.0056 (6)
C8	0.0477 (10)	0.0447 (10)	0.0582 (11)	−0.0021 (8)	0.0178 (9)	−0.0059 (8)
C9	0.0559 (12)	0.0567 (13)	0.0906 (16)	−0.0078 (10)	0.0360 (12)	−0.0249 (12)
C10	0.0721 (14)	0.0690 (14)	0.0807 (15)	−0.0302 (12)	0.0491 (13)	−0.0313 (12)
C11	0.0796 (15)	0.0617 (13)	0.0586 (12)	−0.0225 (11)	0.0377 (12)	−0.0074 (10)
C12	0.0568 (11)	0.0444 (10)	0.0514 (10)	−0.0058 (8)	0.0234 (9)	−0.0009 (8)
C13	0.0315 (8)	0.0431 (9)	0.0488 (9)	0.0015 (7)	0.0091 (7)	0.0029 (7)
C14	0.0369 (9)	0.0475 (10)	0.0594 (11)	−0.0039 (8)	0.0076 (9)	0.0079 (8)
C15	0.0550 (12)	0.0554 (12)	0.0684 (13)	−0.0029 (10)	0.0138 (11)	0.0173 (10)
C16	0.0609 (13)	0.0701 (14)	0.0577 (12)	0.0018 (11)	0.0028 (11)	0.0188 (11)
C17	0.0433 (11)	0.0793 (15)	0.0615 (13)	−0.0053 (11)	−0.0057 (10)	0.0118 (11)
C18	0.0340 (9)	0.0624 (12)	0.0614 (12)	−0.0061 (8)	0.0077 (9)	0.0094 (10)
C19	0.0508 (11)	0.0727 (14)	0.0510 (11)	−0.0044 (10)	0.0170 (9)	0.0103 (10)
C20	0.096 (2)	0.0965 (19)	0.0498 (12)	−0.0058 (16)	0.0236 (13)	0.0015 (12)
C21	0.104 (2)	0.139 (3)	0.0702 (16)	−0.043 (2)	0.0331 (16)	0.0237 (17)
C22	0.0305 (8)	0.0454 (9)	0.0335 (7)	−0.0032 (7)	0.0076 (6)	0.0004 (7)
C23	0.0312 (8)	0.0503 (10)	0.0426 (9)	−0.0025 (7)	0.0036 (7)	−0.0051 (8)
C24	0.0332 (9)	0.0517 (10)	0.0541 (10)	−0.0021 (8)	0.0085 (8)	0.0071 (8)
C25	0.0601 (14)	0.0748 (16)	0.0668 (14)	0.0057 (12)	−0.0146 (12)	0.0038 (12)
N1	0.0279 (6)	0.0386 (7)	0.0373 (7)	−0.0025 (5)	0.0077 (5)	−0.0008 (5)
N2	0.0495 (10)	0.0756 (13)	0.0749 (12)	0.0097 (9)	0.0185 (9)	−0.0033 (10)
N3	0.0576 (12)	0.0761 (14)	0.1063 (17)	0.0158 (11)	0.0254 (12)	−0.0021 (13)
N4	0.0472 (10)	0.0623 (12)	0.1054 (17)	0.0130 (9)	0.0089 (11)	0.0096 (11)
N5	0.0376 (8)	0.0515 (9)	0.0681 (11)	0.0017 (7)	0.0009 (8)	0.0113 (8)
O1	0.0542 (9)	0.0838 (11)	0.0987 (12)	−0.0338 (8)	0.0320 (9)	−0.0138 (9)
O2	0.0399 (7)	0.0483 (7)	0.0540 (7)	−0.0035 (5)	0.0104 (6)	−0.0138 (6)
S1	0.0327 (2)	0.0534 (3)	0.0470 (3)	−0.00136 (19)	0.00093 (18)	−0.0049 (2)
O1W	0.275 (9)	0.202 (7)	0.68 (2)	0.000	0.242 (13)	0.000

Geometric parameters (Å, º) top

C2—N1	1.489 (2)	C16—C17	1.370 (3)
C2—C13	1.532 (2)	C16—H16	0.9300
C2—C3	1.535 (2)	C17—C18	1.390 (3)
C2—H2	0.9800	C17—H17	0.9300
C3—C4	1.507 (3)	C18—H18	0.9300
C3—C19	1.551 (3)	C19—C20	1.522 (3)
C3—H3	0.9800	C19—C21	1.530 (3)
C4—O1	1.209 (2)	C19—H19	0.9800
C4—C5	1.503 (3)	C20—H20A	0.9600
C5—C6	1.533 (2)	C20—H20B	0.9600
C5—H5A	0.9700	C20—H20C	0.9600
C5—H5B	0.9700	C21—H21A	0.9600
C6—N1	1.484 (2)	C21—H21B	0.9600
C6—C7	1.514 (2)	C21—H21C	0.9600
C6—H6	0.9800	C22—O2	1.228 (2)
C7—C8	1.383 (3)	C22—N1	1.357 (2)
C7—C12	1.385 (3)	C22—C23	1.517 (2)
C8—C9	1.379 (3)	C23—S1	1.8052 (17)
C8—H8	0.9300	C23—H23A	0.9700
C9—C10	1.367 (4)	C23—H23B	0.9700
C9—H9	0.9300	C24—N2	1.313 (3)
C10—C11	1.378 (3)	C24—N5	1.338 (2)
C10—H10	0.9300	C24—S1	1.741 (2)
C11—C12	1.374 (3)	C25—N5	1.452 (3)
C11—H11	0.9300	C25—H25A	0.9600
C12—H12	0.9300	C25—H25B	0.9600
C13—C14	1.382 (3)	C25—H25C	0.9600
C13—C18	1.385 (2)	N2—N3	1.362 (3)
C14—C15	1.384 (3)	N3—N4	1.279 (3)
C14—H14	0.9300	N4—N5	1.347 (3)
C15—C16	1.372 (3)	O1W—H1W	0.8163
C15—H15	0.9300

N1—C2—C13	111.48 (14)	C17—C16—H16	120.2
N1—C2—C3	109.35 (14)	C15—C16—H16	120.2
C13—C2—C3	114.81 (14)	C16—C17—C18	120.61 (19)
N1—C2—H2	106.9	C16—C17—H17	119.7
C13—C2—H2	106.9	C18—C17—H17	119.7
C3—C2—H2	106.9	C13—C18—C17	120.36 (19)
C4—C3—C2	109.80 (15)	C13—C18—H18	119.8
C4—C3—C19	109.92 (17)	C17—C18—H18	119.8
C2—C3—C19	113.18 (15)	C20—C19—C21	110.3 (2)
C4—C3—H3	107.9	C20—C19—C3	111.99 (19)
C2—C3—H3	107.9	C21—C19—C3	111.05 (18)
C19—C3—H3	107.9	C20—C19—H19	107.8
O1—C4—C5	120.56 (19)	C21—C19—H19	107.8
O1—C4—C3	123.12 (19)	C3—C19—H19	107.8
C5—C4—C3	116.29 (15)	C19—C20—H20A	109.5
C4—C5—C6	116.04 (15)	C19—C20—H20B	109.5
C4—C5—H5A	108.3	H20A—C20—H20B	109.5
C6—C5—H5A	108.3	C19—C20—H20C	109.5
C4—C5—H5B	108.3	H20A—C20—H20C	109.5
C6—C5—H5B	108.3	H20B—C20—H20C	109.5
H5A—C5—H5B	107.4	C19—C21—H21A	109.5
N1—C6—C7	113.78 (13)	C19—C21—H21B	109.5
N1—C6—C5	110.17 (14)	H21A—C21—H21B	109.5
C7—C6—C5	108.64 (14)	C19—C21—H21C	109.5
N1—C6—H6	108.0	H21A—C21—H21C	109.5
C7—C6—H6	108.0	H21B—C21—H21C	109.5
C5—C6—H6	108.0	O2—C22—N1	123.69 (16)
C8—C7—C12	118.77 (18)	O2—C22—C23	119.90 (15)
C8—C7—C6	119.93 (16)	N1—C22—C23	116.41 (14)
C12—C7—C6	121.23 (16)	C22—C23—S1	108.28 (12)
C9—C8—C7	120.4 (2)	C22—C23—H23A	110.0
C9—C8—H8	119.8	S1—C23—H23A	110.0
C7—C8—H8	119.8	C22—C23—H23B	110.0
C10—C9—C8	120.5 (2)	S1—C23—H23B	110.0
C10—C9—H9	119.7	H23A—C23—H23B	108.4
C8—C9—H9	119.7	N2—C24—N5	108.97 (18)
C9—C10—C11	119.5 (2)	N2—C24—S1	127.57 (15)
C9—C10—H10	120.3	N5—C24—S1	123.46 (16)
C11—C10—H10	120.3	N5—C25—H25A	109.5
C12—C11—C10	120.5 (2)	N5—C25—H25B	109.5
C12—C11—H11	119.8	H25A—C25—H25B	109.5
C10—C11—H11	119.8	N5—C25—H25C	109.5
C11—C12—C7	120.4 (2)	H25A—C25—H25C	109.5
C11—C12—H12	119.8	H25B—C25—H25C	109.5
C7—C12—H12	119.8	C22—N1—C6	121.37 (13)
C14—C13—C18	118.14 (17)	C22—N1—C2	118.73 (14)
C14—C13—C2	118.02 (15)	C6—N1—C2	119.27 (13)
C18—C13—C2	123.84 (17)	C24—N2—N3	105.37 (19)
C13—C14—C15	121.32 (18)	N4—N3—N2	111.0 (2)
C13—C14—H14	119.3	N3—N4—N5	106.89 (18)
C15—C14—H14	119.3	C24—N5—N4	107.78 (19)
C16—C15—C14	120.0 (2)	C24—N5—C25	130.34 (19)
C16—C15—H15	120.0	N4—N5—C25	121.86 (18)
C14—C15—H15	120.0	C24—S1—C23	96.05 (9)
C17—C16—C15	119.6 (2)

N1—C2—C3—C4	59.75 (18)	C2—C13—C18—C17	179.1 (2)
C13—C2—C3—C4	−66.4 (2)	C16—C17—C18—C13	0.4 (4)
N1—C2—C3—C19	−63.5 (2)	C4—C3—C19—C20	−176.12 (19)
C13—C2—C3—C19	170.36 (17)	C2—C3—C19—C20	−53.0 (2)
C2—C3—C4—O1	155.9 (2)	C4—C3—C19—C21	60.0 (3)
C19—C3—C4—O1	−79.0 (2)	C2—C3—C19—C21	−176.8 (2)
C2—C3—C4—C5	−22.2 (2)	O2—C22—C23—S1	−14.3 (2)
C19—C3—C4—C5	102.97 (19)	N1—C22—C23—S1	166.62 (12)
O1—C4—C5—C6	151.13 (19)	O2—C22—N1—C6	−179.37 (15)
C3—C4—C5—C6	−30.8 (2)	C23—C22—N1—C6	−0.3 (2)
C4—C5—C6—N1	45.1 (2)	O2—C22—N1—C2	9.8 (2)
C4—C5—C6—C7	170.36 (15)	C23—C22—N1—C2	−171.18 (14)
N1—C6—C7—C8	−135.30 (16)	C7—C6—N1—C22	61.59 (19)
C5—C6—C7—C8	101.58 (18)	C5—C6—N1—C22	−176.13 (14)
N1—C6—C7—C12	47.8 (2)	C7—C6—N1—C2	−127.61 (15)
C5—C6—C7—C12	−75.3 (2)	C5—C6—N1—C2	−5.3 (2)
C12—C7—C8—C9	0.9 (3)	C13—C2—N1—C22	−107.47 (17)
C6—C7—C8—C9	−176.10 (17)	C3—C2—N1—C22	124.49 (16)
C7—C8—C9—C10	−0.2 (3)	C13—C2—N1—C6	81.48 (17)
C8—C9—C10—C11	−0.7 (3)	C3—C2—N1—C6	−46.55 (19)
C9—C10—C11—C12	1.0 (3)	N5—C24—N2—N3	0.1 (2)
C10—C11—C12—C7	−0.3 (3)	S1—C24—N2—N3	−179.61 (17)
C8—C7—C12—C11	−0.7 (3)	C24—N2—N3—N4	0.3 (3)
C6—C7—C12—C11	176.30 (17)	N2—N3—N4—N5	−0.6 (3)
N1—C2—C13—C14	55.1 (2)	N2—C24—N5—N4	−0.4 (2)
C3—C2—C13—C14	−179.87 (17)	S1—C24—N5—N4	179.29 (15)
N1—C2—C13—C18	−125.88 (19)	N2—C24—N5—C25	177.7 (2)
C3—C2—C13—C18	−0.8 (3)	S1—C24—N5—C25	−2.5 (3)
C18—C13—C14—C15	2.1 (3)	N3—N4—N5—C24	0.6 (3)
C2—C13—C14—C15	−178.76 (19)	N3—N4—N5—C25	−177.7 (2)
C13—C14—C15—C16	−1.1 (4)	N2—C24—S1—C23	−19.8 (2)
C14—C15—C16—C17	−0.4 (4)	N5—C24—S1—C23	160.54 (17)
C15—C16—C17—C18	0.7 (4)	C22—C23—S1—C24	−176.64 (13)
C14—C13—C18—C17	−1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···O1ⁱ	0.96	2.47	3.406 (3)	166
C18—H18···O1ⁱⁱ	0.93	2.54	3.312 (2)	140
C25—H25B···N4ⁱⁱⁱ	0.96	2.54	3.472 (3)	165

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25C···O1ⁱ	0.96	2.47	3.406 (3)	166.2
C18—H18···O1ⁱⁱ	0.93	2.54	3.312 (2)	140.4
C25—H25B···N4ⁱⁱⁱ	0.96	2.54	3.472 (3)	164.7

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z.

Acknowledgements

SG wishes to thank Orchid Chemicals and Pharmaceuticals Limited (www.orchidpharma.com), Chennai, India, for consent to perform the research. PS thanks the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students.

References

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Volume 69| Part 11| November 2013| Page o1598

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3-Iso­propyl-1-{2-[(1-methyl-1H-tetra­zol-5-yl)sulfan­yl]acet­yl}-2,6-di­phenyl­piperidin-4-one hemihydrate

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3-Isopropyl-1-{2-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]acetyl}-2,6-diphenylpiperidin-4-one hemihydrate