Crystal structure of (E)-4-(acet­oxy­imino)-N-allyl-3-isopropyl-2,6-di­phenyl­piperi­dine-1-carbo­thio­amide

Mohandas, T.; Krishnan, K.G.; Balamurugan, S.; Harrison, W.T.A.; Thanikachalam, V.; Sakthivel, P.

doi:10.1107/S2056989015012499

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 8| August 2015| Pages o542-o543

https://doi.org/10.1107/S2056989015012499

Open

access

Crystal structure of (E)-4-(acetoxyimino)-N-allyl-3-isopropyl-2,6-diphenylpiperidine-1-carbothioamide

T. Mohandas,^a K. Gokula Krishnan,^b S. Balamurugan,^c William T. A. Harrison,^d V. Thanikachalam ^b and P. Sakthivel ^e ^*

^aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of Physics, Rover College of Engineering and Technology, Perambalur, India, ^dDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland, and ^eDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli, India
^*Correspondence e-mail: sakthi2udc@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 June 2015; accepted 29 June 2015; online 4 July 2015)

The title compound, C₂₆H₃₁N₃O₂S, crystallizes with two molecules (A and B) in the asymmetric unit. In each case, the piperidine ring exists in a twist-boat conformation. The dihedral angle between the phenyl rings is 46.16 (12)° in molecule A and 44.95 (12)° in molecule B. In both molecules, the allyl side chain is disordered over two orientations in a 0.649 (9):0.351 (9) ratio for molecule A and 0.826 (10):0.174 (10) ratio for molecule B. In the crystal, neither molecule forms a hydrogen bond from its N—H group, presumably due to steric hindrance. A+A and B+B inversion dimers are formed, linked by pairs of weak C—H⋯O hydrogen bonds enclosing R₂²(22) ring motifs.

Keywords: crystal structure; carbothioamide; piperidine; acetoxyimino; inversion dimers.

CCDC reference: 1024973

1. Related literature

For the structural properties and biological potentials of carbothioamides, see: Wilkerson et al. (1996 ); Koca et al. (2013 ); Liu et al. (2012 ); Malik et al.(2013 ). For related structures, see: Park et al. (2012a ,b ).

2. Experimental

2.1. Crystal data

C₂₆H₃₁N₃O₂S
M_r = 449.60
Triclinic, $[P \overline 1]$
a = 12.0434 (6) Å
b = 14.0479 (7) Å
c = 15.2740 (7) Å
α = 82.161 (2)°
β = 72.463 (2)°
γ = 80.094 (2)°
V = 2417.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.28 × 0.25 × 0.24 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.956, T_max = 0.962
74637 measured reflections
11303 independent reflections
6065 reflections with I > 2σ(I)
R_int = 0.050

2.3. Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.146
S = 1.01
11303 reflections
627 parameters
93 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.59	3.298 (4)	133
C2′—H2′⋯O2′ⁱⁱ	0.93	2.59	3.332 (4)	137
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+2, -z+1.

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 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1024973

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015012499/su5159sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012499/su5159Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015012499/su5159Isup3.cml

checkCIF report

Structural commentary top

The chemistry of carbothioamide derivatives are much explored today because of their structural properties and their biological potential as anti-HIV (Wilkerson et al., 1996), anticancer (Koca et al., 2013), antitubercular (Liu et al.2012), and anticonvulsant (Malik et al., 2013) agents.

The bond distances and bond angles in the two independent molecules (A and B) of the title compound, Fig. 1, agree well with those reported for closely related compounds (Park et al., 2012a,b). In each molecule the piperidine ring exists in a twist-boat conformation with the puckering parameters Q = 0.7236, θ = 96.90 (19) and π = 267.97 (19) Å in A and Q = 0.7245, θ = 82.9 (2) and π = 87.38 (19) Å in B. The dihedral angle between the phenyl rings is 46.13 (13) ° in molecule A and 44.97 (13)° in molecule B.

In the crystal, the individual molecules form A—A and B—B inversion dimers with R₂²(22) ring motifs (Table 1 and Fig. 2).

Synthesis and crystallization top

To a solution of 3-isopropyl-2,6-diphenylpiperidin-4-one O-acetyl oxime (0.5 g, 1.5 mmol) in dry DCM (5 ml), pyridine (1.5 eq) and allylisothiocyanate (0.17 g, 1.75 mmol) were added drop wise over 5 min to a 50 ml Erlenmeyer flask. The reaction mixture was subjected to ultrasound irradiation for 1 h at ambient temperature and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was slowly poured into crushed ice giving the crude product as a precipitate. It was subjected to recrystallization from absolute ethanol giving the title compound in good yield (0.62 g, 76%), as colourless block-like crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The positions of the hydrogen atoms bound to the N and C atoms were identified from difference electron density maps. The NH H atoms were refined with U_iso(H) = 1.2U_eq(N). The C-bound H atoms were refined as riding atoms: C—H = 0.93 - 0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms. The atoms of the allyl groups (C19, C20 and C21) are disordered over two orientations in a 0.649 (9):0.351 (9) ratio for molecule A, and a 0.826 (10):0.174 (10) ratio for atom C21' in molecule B. They were modelled with restrained bonds and angles based on the average values found for a non-disordered allyl group.

Related literature top

For the structural properties and biological potentials of carbothiamides, see: Wilkerson et al. (1996); Koca et al. (2013); Liu et al. (2012); Malik et al.(2013). For related structures, see: Park et al. (2012a,b).

Structure description top

In the crystal, the individual molecules form A—A and B—B inversion dimers with R₂²(22) ring motifs (Table 1 and Fig. 2).

Synthesis and crystallization top

Refinement details top

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) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of molecule A of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular structure of molecule B of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. A partial view of the crystal packing of the title compound, with the C—H···O hydrogen bonds shown as dashed lines (see Table 1 for details). Other H atoms and the minor components of the allyl groups have been omitted for clarity.

(E)-4-(Acetoxyimino)-N-allyl-3-isopropyl-2,6-diphenylpiperidine-1-carbothioamide top

Crystal data top

C₂₆H₃₁N₃O₂S	Z = 4
M_r = 449.60	F(000) = 960
Triclinic, P1	D_x = 1.235 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.0434 (6) Å	Cell parameters from 6065 reflections
b = 14.0479 (7) Å	θ = 1.5–27.8°
c = 15.2740 (7) Å	µ = 0.16 mm⁻¹
α = 82.161 (2)°	T = 293 K
β = 72.463 (2)°	Block, colourless
γ = 80.094 (2)°	0.28 × 0.25 × 0.24 mm
V = 2417.4 (2) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	11303 independent reflections
Radiation source: fine-focus sealed tube	6065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω & φ scans	θ_max = 27.8°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.956, T_max = 0.962	k = −18→18
74637 measured reflections	l = −19→19

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)] = 0.049	Hydrogen site location: mixed
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0578P)² + 0.7614P] where P = (F_o² + 2F_c²)/3
11303 reflections	(Δ/σ)_max = 0.001
627 parameters	Δρ_max = 0.19 e Å⁻³
93 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₆H₃₁N₃O₂S	γ = 80.094 (2)°
M_r = 449.60	V = 2417.4 (2) Å³
Triclinic, P1	Z = 4
a = 12.0434 (6) Å	Mo Kα radiation
b = 14.0479 (7) Å	µ = 0.16 mm⁻¹
c = 15.2740 (7) Å	T = 293 K
α = 82.161 (2)°	0.28 × 0.25 × 0.24 mm
β = 72.463 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	11303 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	6065 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.962	R_int = 0.050
74637 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	93 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
11303 reflections	Δρ_min = −0.24 e Å⁻³
627 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.9104 (2)	0.32104 (16)	0.16483 (16)	0.0505 (6)
H1	0.8287	0.3293	0.1823	0.061*
C2	0.9726 (3)	0.25361 (18)	0.10359 (18)	0.0634 (7)
H2	0.9324	0.2168	0.0804	0.076*
C3	1.0929 (3)	0.24062 (19)	0.07682 (18)	0.0679 (8)
H3	1.1347	0.1957	0.0350	0.082*
C4	1.1506 (2)	0.29384 (19)	0.11184 (19)	0.0666 (8)
H4	1.2324	0.2848	0.0942	0.080*
C5	1.0898 (2)	0.36120 (17)	0.17328 (17)	0.0546 (6)
H5	1.1309	0.3968	0.1967	0.065*
C6	0.96801 (19)	0.37627 (15)	0.20040 (14)	0.0414 (5)
C7	0.89823 (17)	0.44607 (15)	0.27223 (14)	0.0392 (5)
H7	0.8777	0.4069	0.3315	0.047*
C8	0.96601 (18)	0.52344 (15)	0.28429 (14)	0.0398 (5)
H8	1.0386	0.4899	0.2971	0.048*
C9	1.00053 (18)	0.58243 (14)	0.19289 (14)	0.0394 (5)
C10	0.91588 (18)	0.59728 (15)	0.13722 (14)	0.0410 (5)
H10C	0.9416	0.5509	0.0911	0.049*
H10D	0.9167	0.6618	0.1052	0.049*
C11	0.78954 (17)	0.58595 (14)	0.19439 (13)	0.0375 (5)
H11	0.7606	0.6397	0.2338	0.045*
C12	0.71303 (18)	0.59542 (15)	0.13008 (14)	0.0400 (5)
C13	0.7181 (2)	0.52194 (17)	0.07673 (16)	0.0521 (6)
H13	0.7691	0.4647	0.0799	0.063*
C14	0.6473 (2)	0.5336 (2)	0.01873 (18)	0.0650 (7)
H14	0.6509	0.4839	−0.0168	0.078*
C15	0.5724 (2)	0.6170 (2)	0.01290 (19)	0.0692 (8)
H15	0.5240	0.6235	−0.0255	0.083*
C16	0.5684 (2)	0.6912 (2)	0.06366 (19)	0.0648 (7)
H16	0.5184	0.7487	0.0588	0.078*
C17	0.6389 (2)	0.68088 (17)	0.12239 (16)	0.0514 (6)
H17	0.6362	0.7316	0.1566	0.062*
C18	0.68301 (18)	0.46797 (15)	0.31362 (14)	0.0403 (5)
C19	0.4679 (7)	0.5156 (14)	0.3736 (6)	0.055 (2)	0.649 (9)
H19A	0.4322	0.5710	0.4089	0.066*	0.649 (9)
H19B	0.4741	0.4591	0.4171	0.066*	0.649 (9)
C20	0.3887 (7)	0.5005 (5)	0.3198 (4)	0.073 (2)	0.649 (9)
H20A	0.3097	0.5017	0.3523	0.088*	0.649 (9)
C21	0.4150 (8)	0.4867 (6)	0.2373 (4)	0.107 (3)	0.649 (9)
H21A	0.4926	0.4847	0.2011	0.129*	0.649 (9)
H21B	0.3570	0.4782	0.2115	0.129*	0.649 (9)
C19A	0.4658 (12)	0.509 (2)	0.3549 (12)	0.051 (4)	0.351 (9)
H19C	0.4126	0.5685	0.3711	0.061*	0.351 (9)
H19D	0.4597	0.4656	0.4106	0.061*	0.351 (9)
C20A	0.4303 (10)	0.4633 (11)	0.2866 (13)	0.080 (4)	0.351 (9)
H20C	0.4864	0.4176	0.2531	0.096*	0.351 (9)
C21A	0.3336 (10)	0.4799 (8)	0.2700 (9)	0.094 (4)	0.351 (9)
H21C	0.2744	0.5250	0.3017	0.113*	0.351 (9)
H21D	0.3205	0.4471	0.2259	0.113*	0.351 (9)
C22	1.2103 (2)	0.71539 (19)	0.0584 (2)	0.0602 (7)
C23	1.2410 (3)	0.7428 (2)	0.1369 (2)	0.0812 (9)
H23A	1.2808	0.6869	0.1642	0.122*
H23B	1.1707	0.7672	0.1819	0.122*
H23C	1.2916	0.7921	0.1157	0.122*
C24	0.9001 (2)	0.58617 (17)	0.36463 (15)	0.0495 (6)
H24	0.8309	0.6245	0.3499	0.059*
C25	0.9766 (2)	0.65575 (19)	0.37572 (18)	0.0647 (7)
H25A	1.0489	0.6200	0.3838	0.097*
H25B	0.9362	0.6907	0.4287	0.097*
H25C	0.9934	0.7007	0.3217	0.097*
C26	0.8579 (3)	0.5235 (2)	0.45415 (17)	0.0723 (8)
H26A	0.9227	0.4780	0.4649	0.108*
H26B	0.7978	0.4890	0.4499	0.108*
H26C	0.8267	0.5640	0.5042	0.108*
N1	0.78573 (14)	0.49402 (11)	0.25558 (11)	0.0373 (4)
N2	0.58584 (15)	0.53170 (13)	0.31824 (13)	0.0453 (5)
H2A	0.590 (2)	0.5882 (13)	0.2876 (15)	0.054*
N3	1.10177 (16)	0.60888 (13)	0.16899 (12)	0.0471 (5)
S1	0.67667 (6)	0.35980 (4)	0.37701 (5)	0.05813 (19)
O1	1.12691 (13)	0.65613 (12)	0.07647 (11)	0.0552 (4)
O2	1.25123 (18)	0.74278 (16)	−0.02053 (15)	0.0901 (7)
C1'	0.6908 (2)	0.82063 (16)	0.39025 (18)	0.0530 (6)
H1'	0.6887	0.8289	0.3293	0.064*
C2'	0.6264 (2)	0.75462 (18)	0.4523 (2)	0.0675 (8)
H2'	0.5812	0.7192	0.4328	0.081*
C3'	0.6292 (3)	0.7414 (2)	0.5417 (2)	0.0747 (9)
H3'	0.5852	0.6976	0.5833	0.090*
C4'	0.6960 (3)	0.7921 (2)	0.56967 (19)	0.0746 (8)
H4'	0.6988	0.7822	0.6305	0.090*
C5'	0.7602 (2)	0.85858 (17)	0.50906 (16)	0.0579 (7)
H5'	0.8054	0.8931	0.5296	0.069*
C6'	0.75794 (18)	0.87427 (14)	0.41829 (15)	0.0418 (5)
C7'	0.83309 (19)	0.94263 (15)	0.34869 (14)	0.0407 (5)
H7'	0.9052	0.9025	0.3168	0.049*
C8'	0.87150 (18)	1.01997 (15)	0.39090 (15)	0.0430 (5)
H8'	0.9098	0.9862	0.4369	0.052*
C9'	0.76054 (19)	1.08015 (15)	0.44174 (15)	0.0413 (5)
C10'	0.66016 (18)	1.09535 (15)	0.40147 (14)	0.0418 (5)
H10A	0.6182	1.1601	0.4117	0.050*
H10B	0.6064	1.0495	0.4334	0.050*
C11'	0.69701 (17)	1.08337 (14)	0.29862 (14)	0.0376 (5)
H11'	0.7406	1.1369	0.2666	0.045*
C12'	0.58795 (18)	1.09288 (15)	0.26641 (13)	0.0387 (5)
C13'	0.5171 (2)	1.02040 (17)	0.28710 (17)	0.0523 (6)
H13'	0.5363	0.9635	0.3215	0.063*
C14'	0.4187 (2)	1.0319 (2)	0.2571 (2)	0.0654 (7)
H14'	0.3718	0.9827	0.2715	0.078*
C15'	0.3888 (2)	1.1149 (2)	0.20649 (19)	0.0663 (7)
H15'	0.3228	1.1217	0.1854	0.080*
C16'	0.4564 (2)	1.1878 (2)	0.18714 (18)	0.0644 (7)
H16'	0.4356	1.2450	0.1537	0.077*
C17'	0.5557 (2)	1.17704 (17)	0.21699 (15)	0.0513 (6)
H17'	0.6012	1.2272	0.2035	0.062*
C18'	0.82442 (18)	0.96574 (15)	0.18875 (15)	0.0426 (5)
C19'	0.8314 (2)	1.0136 (2)	0.02547 (16)	0.0624 (7)
H19E	0.8962	0.9610	0.0135	0.075*
H19F	0.8592	1.0713	−0.0113	0.075*
C20'	0.7370 (4)	0.9896 (3)	−0.0056 (3)	0.1015 (12)
H20E	0.7519	0.9936	−0.0693	0.122*	0.826 (10)
H20F	0.7353	0.9249	0.0174	0.122*	0.174 (10)
C21'	0.6441 (5)	0.9659 (5)	0.0372 (5)	0.130 (3)	0.826 (10)
H21E	0.6225	0.9602	0.1013	0.156*	0.826 (10)
H21F	0.5931	0.9530	0.0064	0.156*	0.826 (10)
C21B	0.6593 (18)	1.003 (2)	−0.0433 (18)	0.111 (9)	0.174 (10)
H21G	0.6414	1.0634	−0.0730	0.133*	0.174 (10)
H21H	0.6178	0.9527	−0.0424	0.133*	0.174 (10)
C22'	0.6484 (3)	1.21816 (19)	0.6224 (2)	0.0672 (8)
C23'	0.7637 (3)	1.2480 (3)	0.6141 (3)	0.1040 (12)
H23D	0.7529	1.2970	0.6551	0.156*
H23E	0.7973	1.2735	0.5518	0.156*
H23F	0.8154	1.1928	0.6299	0.156*
C24'	0.9607 (2)	1.07945 (18)	0.32045 (17)	0.0546 (6)
H24'	0.9267	1.1084	0.2706	0.066*
C25'	1.0733 (3)	1.0147 (2)	0.2795 (3)	0.0981 (11)
H25D	1.1302	1.0535	0.2399	0.147*
H25E	1.0581	0.9693	0.2443	0.147*
H25F	1.1033	0.9800	0.3281	0.147*
C26'	0.9864 (3)	1.1606 (2)	0.3641 (2)	0.0795 (9)
H26D	1.0106	1.1343	0.4179	0.119*
H26E	0.9168	1.2069	0.3813	0.119*
H26F	1.0481	1.1920	0.3207	0.119*
N1'	0.77728 (14)	0.99094 (12)	0.27709 (11)	0.0382 (4)
N2'	0.80050 (17)	1.03032 (14)	0.12168 (12)	0.0464 (5)
H2B	0.7510 (18)	1.0837 (13)	0.1341 (16)	0.056*
N3'	0.76056 (18)	1.10743 (14)	0.51771 (13)	0.0514 (5)
S1'	0.90805 (6)	0.85825 (5)	0.16427 (5)	0.0636 (2)
O1'	0.64564 (15)	1.15591 (12)	0.56286 (11)	0.0583 (4)
O2'	0.5553 (2)	1.24742 (16)	0.67412 (15)	0.0951 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0547 (15)	0.0396 (13)	0.0555 (14)	−0.0050 (11)	−0.0158 (12)	−0.0004 (11)
C2	0.088 (2)	0.0427 (14)	0.0590 (16)	−0.0050 (14)	−0.0216 (15)	−0.0058 (12)
C3	0.086 (2)	0.0431 (15)	0.0578 (16)	0.0035 (14)	−0.0022 (15)	−0.0052 (12)
C4	0.0585 (17)	0.0486 (15)	0.0714 (18)	0.0025 (13)	0.0057 (14)	−0.0008 (13)
C5	0.0480 (14)	0.0438 (13)	0.0638 (16)	−0.0055 (11)	−0.0050 (12)	−0.0031 (12)
C6	0.0415 (12)	0.0338 (11)	0.0417 (12)	−0.0031 (9)	−0.0059 (10)	0.0050 (9)
C7	0.0349 (11)	0.0383 (11)	0.0395 (11)	−0.0034 (9)	−0.0082 (9)	0.0054 (9)
C8	0.0346 (11)	0.0421 (12)	0.0419 (12)	−0.0029 (9)	−0.0131 (9)	0.0005 (9)
C9	0.0368 (12)	0.0357 (11)	0.0448 (12)	−0.0053 (9)	−0.0092 (10)	−0.0056 (9)
C10	0.0421 (12)	0.0394 (12)	0.0401 (12)	−0.0113 (10)	−0.0103 (10)	0.0049 (9)
C11	0.0417 (12)	0.0317 (11)	0.0370 (11)	−0.0052 (9)	−0.0108 (9)	0.0032 (9)
C12	0.0372 (12)	0.0403 (12)	0.0396 (12)	−0.0087 (9)	−0.0096 (9)	0.0076 (9)
C13	0.0595 (15)	0.0462 (14)	0.0549 (14)	−0.0103 (11)	−0.0240 (12)	0.0026 (11)
C14	0.0779 (19)	0.0685 (18)	0.0614 (16)	−0.0261 (15)	−0.0349 (15)	0.0058 (14)
C15	0.0659 (18)	0.089 (2)	0.0623 (17)	−0.0299 (17)	−0.0349 (15)	0.0215 (16)
C16	0.0457 (15)	0.0737 (19)	0.0645 (17)	0.0002 (13)	−0.0165 (13)	0.0205 (15)
C17	0.0465 (14)	0.0527 (14)	0.0488 (14)	−0.0010 (11)	−0.0122 (11)	0.0061 (11)
C18	0.0397 (12)	0.0403 (12)	0.0406 (12)	−0.0073 (10)	−0.0117 (10)	0.0002 (9)
C19	0.037 (3)	0.066 (5)	0.054 (4)	−0.012 (3)	−0.005 (2)	0.007 (3)
C20	0.051 (4)	0.082 (4)	0.083 (4)	−0.012 (3)	−0.013 (3)	−0.001 (3)
C21	0.088 (6)	0.156 (6)	0.080 (5)	−0.053 (4)	−0.022 (4)	0.025 (4)
C19A	0.039 (6)	0.047 (6)	0.059 (7)	−0.001 (5)	−0.009 (5)	0.004 (6)
C20A	0.049 (6)	0.090 (7)	0.091 (8)	−0.012 (5)	−0.012 (6)	0.009 (7)
C21A	0.066 (7)	0.134 (9)	0.099 (8)	−0.039 (6)	−0.037 (7)	−0.001 (6)
C22	0.0421 (14)	0.0560 (15)	0.0750 (19)	−0.0132 (12)	−0.0036 (13)	−0.0016 (14)
C23	0.0684 (19)	0.076 (2)	0.106 (2)	−0.0324 (16)	−0.0274 (18)	−0.0004 (18)
C24	0.0475 (14)	0.0577 (14)	0.0440 (13)	0.0017 (11)	−0.0181 (11)	−0.0066 (11)
C25	0.082 (2)	0.0597 (16)	0.0582 (16)	−0.0085 (14)	−0.0262 (14)	−0.0105 (13)
C26	0.083 (2)	0.090 (2)	0.0461 (15)	−0.0248 (17)	−0.0142 (14)	−0.0060 (14)
N1	0.0339 (9)	0.0341 (9)	0.0401 (9)	−0.0045 (7)	−0.0079 (8)	0.0038 (7)
N2	0.0362 (10)	0.0399 (10)	0.0519 (11)	−0.0051 (8)	−0.0049 (8)	0.0056 (9)
N3	0.0432 (11)	0.0488 (11)	0.0482 (11)	−0.0119 (9)	−0.0106 (9)	0.0017 (9)
S1	0.0500 (4)	0.0464 (4)	0.0679 (4)	−0.0117 (3)	−0.0092 (3)	0.0180 (3)
O1	0.0488 (10)	0.0606 (10)	0.0535 (10)	−0.0221 (8)	−0.0063 (8)	0.0031 (8)
O2	0.0786 (14)	0.0983 (16)	0.0796 (14)	−0.0437 (12)	0.0075 (11)	0.0099 (12)
C1'	0.0465 (14)	0.0403 (13)	0.0686 (16)	−0.0029 (11)	−0.0137 (12)	−0.0027 (11)
C2'	0.0510 (16)	0.0415 (14)	0.103 (2)	−0.0102 (12)	−0.0095 (15)	−0.0049 (14)
C3'	0.0719 (19)	0.0481 (16)	0.081 (2)	−0.0151 (14)	0.0111 (16)	0.0051 (15)
C4'	0.098 (2)	0.0552 (16)	0.0550 (16)	−0.0142 (16)	−0.0009 (15)	0.0055 (13)
C5'	0.0719 (18)	0.0496 (14)	0.0477 (14)	−0.0159 (13)	−0.0100 (12)	0.0041 (11)
C6'	0.0385 (12)	0.0332 (11)	0.0475 (13)	−0.0010 (9)	−0.0066 (10)	−0.0008 (9)
C7'	0.0386 (12)	0.0395 (12)	0.0406 (12)	−0.0016 (9)	−0.0112 (10)	0.0024 (9)
C8'	0.0409 (12)	0.0457 (13)	0.0456 (12)	−0.0117 (10)	−0.0191 (10)	0.0078 (10)
C9'	0.0489 (13)	0.0355 (11)	0.0422 (12)	−0.0136 (10)	−0.0163 (10)	0.0040 (9)
C10'	0.0425 (12)	0.0398 (12)	0.0432 (12)	−0.0039 (10)	−0.0122 (10)	−0.0062 (9)
C11'	0.0349 (11)	0.0360 (11)	0.0397 (11)	−0.0048 (9)	−0.0088 (9)	−0.0005 (9)
C12'	0.0367 (12)	0.0424 (12)	0.0350 (11)	−0.0028 (9)	−0.0089 (9)	−0.0026 (9)
C13'	0.0481 (14)	0.0465 (13)	0.0650 (15)	−0.0091 (11)	−0.0236 (12)	0.0052 (11)
C14'	0.0520 (16)	0.0669 (17)	0.0841 (19)	−0.0182 (13)	−0.0278 (14)	0.0013 (15)
C15'	0.0500 (15)	0.087 (2)	0.0677 (17)	−0.0101 (15)	−0.0309 (14)	0.0058 (15)
C16'	0.0554 (16)	0.0728 (18)	0.0589 (16)	−0.0044 (14)	−0.0223 (13)	0.0232 (14)
C17'	0.0439 (13)	0.0552 (14)	0.0501 (14)	−0.0078 (11)	−0.0123 (11)	0.0093 (11)
C18'	0.0393 (12)	0.0427 (12)	0.0438 (13)	−0.0063 (10)	−0.0095 (10)	−0.0013 (10)
C19'	0.0799 (19)	0.0606 (16)	0.0440 (14)	−0.0020 (14)	−0.0168 (13)	−0.0070 (12)
C20'	0.119 (3)	0.099 (3)	0.105 (3)	0.018 (3)	−0.064 (3)	−0.042 (2)
C21'	0.084 (4)	0.188 (6)	0.134 (6)	0.001 (4)	−0.034 (4)	−0.085 (5)
C21B	0.079 (14)	0.18 (2)	0.103 (19)	0.013 (13)	−0.059 (13)	−0.060 (15)
C22'	0.104 (2)	0.0535 (16)	0.0520 (16)	−0.0091 (16)	−0.0336 (17)	−0.0069 (13)
C23'	0.122 (3)	0.087 (2)	0.136 (3)	−0.003 (2)	−0.077 (3)	−0.047 (2)
C24'	0.0420 (13)	0.0625 (15)	0.0613 (15)	−0.0185 (12)	−0.0199 (12)	0.0140 (12)
C25'	0.0522 (18)	0.098 (2)	0.124 (3)	−0.0241 (17)	0.0116 (18)	−0.011 (2)
C26'	0.074 (2)	0.0738 (19)	0.097 (2)	−0.0384 (16)	−0.0282 (17)	0.0160 (17)
N1'	0.0372 (10)	0.0382 (10)	0.0376 (10)	−0.0009 (8)	−0.0109 (8)	−0.0029 (8)
N2'	0.0531 (12)	0.0440 (11)	0.0381 (10)	−0.0011 (9)	−0.0098 (9)	−0.0040 (9)
N3'	0.0611 (13)	0.0496 (11)	0.0488 (12)	−0.0132 (10)	−0.0211 (10)	−0.0031 (9)
S1'	0.0723 (5)	0.0507 (4)	0.0573 (4)	0.0123 (3)	−0.0119 (3)	−0.0111 (3)
O1'	0.0712 (12)	0.0580 (10)	0.0489 (9)	−0.0131 (9)	−0.0154 (9)	−0.0144 (8)
O2'	0.126 (2)	0.0888 (16)	0.0640 (13)	−0.0094 (14)	−0.0098 (13)	−0.0324 (12)

Geometric parameters (Å, º) top

C1—C6	1.380 (3)	N2—H2A	0.866 (15)
C1—C2	1.381 (3)	N3—O1	1.444 (2)
C1—H1	0.9300	C1'—C6'	1.383 (3)
C2—C3	1.369 (4)	C1'—C2'	1.387 (3)
C2—H2	0.9300	C1'—H1'	0.9300
C3—C4	1.357 (4)	C2'—C3'	1.361 (4)
C3—H3	0.9300	C2'—H2'	0.9300
C4—C5	1.379 (3)	C3'—C4'	1.351 (4)
C4—H4	0.9300	C3'—H3'	0.9300
C5—C6	1.385 (3)	C4'—C5'	1.381 (3)
C5—H5	0.9300	C4'—H4'	0.9300
C6—C7	1.525 (3)	C5'—C6'	1.382 (3)
C7—N1	1.484 (2)	C5'—H5'	0.9300
C7—C8	1.527 (3)	C6'—C7'	1.521 (3)
C7—H7	0.9800	C7'—N1'	1.481 (3)
C8—C9	1.504 (3)	C7'—C8'	1.534 (3)
C8—C24	1.543 (3)	C7'—H7'	0.9800
C8—H8	0.9800	C8'—C9'	1.506 (3)
C9—N3	1.268 (3)	C8'—C24'	1.542 (3)
C9—C10	1.485 (3)	C8'—H8'	0.9800
C10—C11	1.532 (3)	C9'—N3'	1.271 (3)
C10—H10C	0.9700	C9'—C10'	1.486 (3)
C10—H10D	0.9700	C10'—C11'	1.523 (3)
C11—N1	1.486 (2)	C10'—H10A	0.9700
C11—C12	1.516 (3)	C10'—H10B	0.9700
C11—H11	0.9800	C11'—N1'	1.490 (3)
C12—C17	1.381 (3)	C11'—C12'	1.515 (3)
C12—C13	1.382 (3)	C11'—H11'	0.9800
C13—C14	1.380 (3)	C12'—C17'	1.376 (3)
C13—H13	0.9300	C12'—C13'	1.383 (3)
C14—C15	1.360 (4)	C13'—C14'	1.371 (3)
C14—H14	0.9300	C13'—H13'	0.9300
C15—C16	1.368 (4)	C14'—C15'	1.366 (4)
C15—H15	0.9300	C14'—H14'	0.9300
C16—C17	1.388 (3)	C15'—C16'	1.363 (4)
C16—H16	0.9300	C15'—H15'	0.9300
C17—H17	0.9300	C16'—C17'	1.381 (3)
C18—N2	1.335 (3)	C16'—H16'	0.9300
C18—N1	1.363 (2)	C17'—H17'	0.9300
C18—S1	1.687 (2)	C18'—N2'	1.338 (3)
C19—N2	1.455 (5)	C18'—N1'	1.367 (3)
C19—C20	1.490 (8)	C18'—S1'	1.685 (2)
C19—H19A	0.9700	C19'—N2'	1.445 (3)
C19—H19B	0.9700	C19'—C20'	1.459 (4)
C20—C21	1.238 (7)	C19'—H19E	0.9700
C20—H20A	0.9300	C19'—H19F	0.9700
C21—H21A	0.9300	C20'—C21'	1.192 (5)
C21—H21B	0.9300	C20'—C21B	1.216 (9)
C19A—N2	1.457 (7)	C20'—H20E	0.9300
C19A—C20A	1.495 (10)	C20'—H20F	0.9300
C19A—H19C	0.9700	C21'—H21E	0.9300
C19A—H19D	0.9700	C21'—H21F	0.9300
C20A—C21A	1.242 (9)	C21B—H21G	0.9300
C20A—H20C	0.9300	C21B—H21H	0.9300
C21A—H21C	0.9300	C22'—O2'	1.203 (3)
C21A—H21D	0.9300	C22'—O1'	1.355 (3)
C22—O2	1.194 (3)	C22'—C23'	1.483 (4)
C22—O1	1.355 (3)	C23'—H23D	0.9600
C22—C23	1.470 (4)	C23'—H23E	0.9600
C23—H23A	0.9600	C23'—H23F	0.9600
C23—H23B	0.9600	C24'—C25'	1.509 (4)
C23—H23C	0.9600	C24'—C26'	1.514 (4)
C24—C25	1.511 (3)	C24'—H24'	0.9800
C24—C26	1.520 (3)	C25'—H25D	0.9600
C24—H24	0.9800	C25'—H25E	0.9600
C25—H25A	0.9600	C25'—H25F	0.9600
C25—H25B	0.9600	C26'—H26D	0.9600
C25—H25C	0.9600	C26'—H26E	0.9600
C26—H26A	0.9600	C26'—H26F	0.9600
C26—H26B	0.9600	N2'—H2B	0.878 (16)
C26—H26C	0.9600	N3'—O1'	1.443 (3)

C6—C1—C2	120.9 (2)	C19—N2—H2A	114.8 (17)
C6—C1—H1	119.5	C19A—N2—H2A	113 (2)
C2—C1—H1	119.5	C9—N3—O1	110.22 (17)
C3—C2—C1	120.4 (3)	C22—O1—N3	113.05 (18)
C3—C2—H2	119.8	C6'—C1'—C2'	120.5 (3)
C1—C2—H2	119.8	C6'—C1'—H1'	119.7
C4—C3—C2	119.3 (3)	C2'—C1'—H1'	119.7
C4—C3—H3	120.3	C3'—C2'—C1'	120.4 (3)
C2—C3—H3	120.3	C3'—C2'—H2'	119.8
C3—C4—C5	120.9 (3)	C1'—C2'—H2'	119.8
C3—C4—H4	119.5	C4'—C3'—C2'	119.7 (3)
C5—C4—H4	119.5	C4'—C3'—H3'	120.1
C4—C5—C6	120.6 (2)	C2'—C3'—H3'	120.1
C4—C5—H5	119.7	C3'—C4'—C5'	120.8 (3)
C6—C5—H5	119.7	C3'—C4'—H4'	119.6
C1—C6—C5	117.8 (2)	C5'—C4'—H4'	119.6
C1—C6—C7	120.21 (19)	C4'—C5'—C6'	120.7 (3)
C5—C6—C7	121.8 (2)	C4'—C5'—H5'	119.7
N1—C7—C6	112.82 (17)	C6'—C5'—H5'	119.7
N1—C7—C8	109.01 (16)	C5'—C6'—C1'	117.9 (2)
C6—C7—C8	114.69 (17)	C5'—C6'—C7'	121.8 (2)
N1—C7—H7	106.6	C1'—C6'—C7'	120.1 (2)
C6—C7—H7	106.6	N1'—C7'—C6'	112.90 (17)
C8—C7—H7	106.6	N1'—C7'—C8'	108.90 (16)
C9—C8—C7	106.97 (17)	C6'—C7'—C8'	114.75 (17)
C9—C8—C24	112.95 (17)	N1'—C7'—H7'	106.6
C7—C8—C24	114.39 (17)	C6'—C7'—H7'	106.6
C9—C8—H8	107.4	C8'—C7'—H7'	106.6
C7—C8—H8	107.4	C9'—C8'—C7'	106.51 (17)
C24—C8—H8	107.4	C9'—C8'—C24'	114.19 (18)
N3—C9—C10	126.87 (19)	C7'—C8'—C24'	113.71 (19)
N3—C9—C8	116.60 (19)	C9'—C8'—H8'	107.4
C10—C9—C8	116.37 (17)	C7'—C8'—H8'	107.4
C9—C10—C11	113.67 (17)	C24'—C8'—H8'	107.4
C9—C10—H10C	108.8	N3'—C9'—C10'	126.9 (2)
C11—C10—H10C	108.8	N3'—C9'—C8'	116.2 (2)
C9—C10—H10D	108.8	C10'—C9'—C8'	116.81 (19)
C11—C10—H10D	108.8	C9'—C10'—C11'	113.53 (18)
H10C—C10—H10D	107.7	C9'—C10'—H10A	108.9
N1—C11—C12	113.53 (16)	C11'—C10'—H10A	108.9
N1—C11—C10	111.00 (16)	C9'—C10'—H10B	108.9
C12—C11—C10	109.06 (16)	C11'—C10'—H10B	108.9
N1—C11—H11	107.7	H10A—C10'—H10B	107.7
C12—C11—H11	107.7	N1'—C11'—C12'	113.42 (16)
C10—C11—H11	107.7	N1'—C11'—C10'	111.21 (16)
C17—C12—C13	119.0 (2)	C12'—C11'—C10'	109.08 (16)
C17—C12—C11	119.2 (2)	N1'—C11'—H11'	107.6
C13—C12—C11	121.78 (19)	C12'—C11'—H11'	107.6
C14—C13—C12	120.0 (2)	C10'—C11'—H11'	107.6
C14—C13—H13	120.0	C17'—C12'—C13'	118.3 (2)
C12—C13—H13	120.0	C17'—C12'—C11'	119.51 (19)
C15—C14—C13	120.9 (3)	C13'—C12'—C11'	122.16 (18)
C15—C14—H14	119.6	C14'—C13'—C12'	120.4 (2)
C13—C14—H14	119.6	C14'—C13'—H13'	119.8
C14—C15—C16	119.8 (2)	C12'—C13'—H13'	119.8
C14—C15—H15	120.1	C15'—C14'—C13'	120.8 (2)
C16—C15—H15	120.1	C15'—C14'—H14'	119.6
C15—C16—C17	120.2 (3)	C13'—C14'—H14'	119.6
C15—C16—H16	119.9	C16'—C15'—C14'	119.5 (2)
C17—C16—H16	119.9	C16'—C15'—H15'	120.3
C12—C17—C16	120.1 (2)	C14'—C15'—H15'	120.3
C12—C17—H17	120.0	C15'—C16'—C17'	120.3 (2)
C16—C17—H17	120.0	C15'—C16'—H16'	119.9
N2—C18—N1	117.20 (17)	C17'—C16'—H16'	119.9
N2—C18—S1	120.64 (16)	C12'—C17'—C16'	120.7 (2)
N1—C18—S1	122.16 (16)	C12'—C17'—H17'	119.6
N2—C19—C20	114.7 (7)	C16'—C17'—H17'	119.6
N2—C19—H19A	108.6	N2'—C18'—N1'	116.93 (19)
C20—C19—H19A	108.6	N2'—C18'—S1'	120.93 (17)
N2—C19—H19B	108.6	N1'—C18'—S1'	122.13 (16)
C20—C19—H19B	108.6	N2'—C19'—C20'	115.6 (3)
H19A—C19—H19B	107.6	N2'—C19'—H19E	108.4
C21—C20—C19	128.1 (9)	C20'—C19'—H19E	108.4
C21—C20—H20A	115.9	N2'—C19'—H19F	108.4
C19—C20—H20A	115.9	C20'—C19'—H19F	108.4
C20—C21—H21A	120.0	H19E—C19'—H19F	107.4
C20—C21—H21B	120.0	C21'—C20'—C19'	130.6 (5)
H21A—C21—H21B	120.0	C21B—C20'—C19'	157.3 (15)
N2—C19A—C20A	111.5 (10)	C21'—C20'—H20E	114.7
N2—C19A—H19C	109.3	C19'—C20'—H20E	114.7
C20A—C19A—H19C	109.3	C21B—C20'—H20F	101.3
N2—C19A—H19D	109.3	C19'—C20'—H20F	101.3
C20A—C19A—H19D	109.3	C20'—C21'—H21E	120.0
H19C—C19A—H19D	108.0	C20'—C21'—H21F	120.0
C21A—C20A—C19A	126.9 (17)	H21E—C21'—H21F	120.0
C21A—C20A—H20C	116.6	C20'—C21B—H21G	120.0
C19A—C20A—H20C	116.6	C20'—C21B—H21H	120.0
C20A—C21A—H21C	120.0	H21G—C21B—H21H	120.0
C20A—C21A—H21D	120.0	O2'—C22'—O1'	116.2 (3)
H21C—C21A—H21D	120.0	O2'—C22'—C23'	126.3 (3)
O2—C22—O1	116.7 (3)	O1'—C22'—C23'	117.4 (3)
O2—C22—C23	125.3 (2)	C22'—C23'—H23D	109.5
O1—C22—C23	118.0 (2)	C22'—C23'—H23E	109.5
C22—C23—H23A	109.5	H23D—C23'—H23E	109.5
C22—C23—H23B	109.5	C22'—C23'—H23F	109.5
H23A—C23—H23B	109.5	H23D—C23'—H23F	109.5
C22—C23—H23C	109.5	H23E—C23'—H23F	109.5
H23A—C23—H23C	109.5	C25'—C24'—C26'	110.1 (2)
H23B—C23—H23C	109.5	C25'—C24'—C8'	110.5 (2)
C25—C24—C26	110.5 (2)	C26'—C24'—C8'	111.3 (2)
C25—C24—C8	110.79 (19)	C25'—C24'—H24'	108.3
C26—C24—C8	111.3 (2)	C26'—C24'—H24'	108.3
C25—C24—H24	108.0	C8'—C24'—H24'	108.3
C26—C24—H24	108.0	C24'—C25'—H25D	109.5
C8—C24—H24	108.0	C24'—C25'—H25E	109.5
C24—C25—H25A	109.5	H25D—C25'—H25E	109.5
C24—C25—H25B	109.5	C24'—C25'—H25F	109.5
H25A—C25—H25B	109.5	H25D—C25'—H25F	109.5
C24—C25—H25C	109.5	H25E—C25'—H25F	109.5
H25A—C25—H25C	109.5	C24'—C26'—H26D	109.5
H25B—C25—H25C	109.5	C24'—C26'—H26E	109.5
C24—C26—H26A	109.5	H26D—C26'—H26E	109.5
C24—C26—H26B	109.5	C24'—C26'—H26F	109.5
H26A—C26—H26B	109.5	H26D—C26'—H26F	109.5
C24—C26—H26C	109.5	H26E—C26'—H26F	109.5
H26A—C26—H26C	109.5	C18'—N1'—C7'	118.81 (17)
H26B—C26—H26C	109.5	C18'—N1'—C11'	121.76 (16)
C18—N1—C7	118.77 (16)	C7'—N1'—C11'	116.86 (16)
C18—N1—C11	121.97 (16)	C18'—N2'—C19'	125.3 (2)
C7—N1—C11	116.89 (15)	C18'—N2'—H2B	121.5 (16)
C18—N2—C19	125.1 (8)	C19'—N2'—H2B	112.1 (16)
C18—N2—C19A	125.4 (13)	C9'—N3'—O1'	110.08 (18)
C18—N2—H2A	120.1 (16)	C22'—O1'—N3'	113.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.59	3.298 (4)	133
C2′—H2′···O2′ⁱⁱ	0.93	2.59	3.332 (4)	137

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.59	3.298 (4)	133
C2'—H2'···O2'ⁱⁱ	0.93	2.59	3.332 (4)	137

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

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Madras, India, for the data collection.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Koca, İ, Özgür, A., Coşkun, K. A. & Tutar, Y. (2013). Bioorg. Med. Chem. 21, 3859–3865. Web of Science CrossRef CAS PubMed Google Scholar
Liu, W., Zhou, J., Zhang, T., Zhu, H., Qian, H., Zhang, H., Huang, W. & Gust, R. (2012). Bioorg. Med. Chem. Lett. 22, 2701–2704. Web of Science CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Malik, S., Bahare, R. S. & Khan, S. A. (2013). Eur. J. Med. Chem. 67, 1–13. Web of Science CrossRef CAS PubMed Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012a). Acta Cryst. E68, o524. Web of Science CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o525. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wilkerson, M. W., Akamike, E., Cheatham, W. W., Hollis, Y. A., Collins, R. D., DeLucca, I. L., Lam, P. Y. S. & Ru, Y. (1996). J. Med. Chem. 39, 4299–4312. CrossRef CAS PubMed Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 8| August 2015| Pages o542-o543

https://doi.org/10.1107/S2056989015012499

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of (E)-4-(acet­­oxy­imino)-N-allyl-3-iso­propyl-2,6-di­phenyl­piperi­dine-1-carbo­thio­amide

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)-4-(acetoxyimino)-N-allyl-3-isopropyl-2,6-diphenylpiperidine-1-carbothioamide