Literature DB >> 21754856

[(1,3-Benzothia-zol-2-yl)amino-carbon-yl]meth-yl piperidine-1-carbodithio-ate monohydrate.

Xu-Jia Lu, Hong-Bin Zhao, Liang Chen, De-Liang Yang, Bang-Ying Wang.

Abstract

In the title compound, C(15)H(17)N(3)OS(3)·H(2)O, the piperidine ring has a chair conformation. The crystal structure is stabilized by weak inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen-bonding inter-actions.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 21754856 PMCID： PMC3120394 DOI： 10.1107/S1600536811018460

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological activity of substituted N-benzothiazol-2-yl-amides, see: Patel & Shaikh (2010 ▶); Hou et al. (2006 ▶). For related structures, see: Wang et al. (2008 ▶).

Experimental

Crystal data

C15H17N3OS3·H2O M = 369.39 Monoclinic, a = 10.6326 (3) Å b = 12.0735 (3) Å c = 14.7824 (4) Å β = 113.133 (2)° V = 1745.08 (8) Å3 Z = 4 Mo Kα radiation μ = 0.44 mm−1 T = 296 K 0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.918, T max = 0.918 15147 measured reflections 3992 independent reflections 3497 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.095 S = 1.11 3992 reflections 202 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.30 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018460/fj2417sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018460/fj2417Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811018460/fj2417Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₇N₃OS₃·H₂O	F(000) = 776
M_r = 369.39	D_x = 1.406 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8358 reflections
a = 10.6326 (3) Å	θ = 3.0–27.5°
b = 12.0735 (3) Å	µ = 0.44 mm⁻¹
c = 14.7824 (4) Å	T = 296 K
β = 113.133 (2)°	Block, colorless
V = 1745.08 (8) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3992 independent reflections
Radiation source: fine-focus sealed tube	3497 reflections with I > 2σ(I)
graphite	R_int = 0.020
φ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→13
T_min = 0.918, T_max = 0.918	k = −14→15
15147 measured reflections	l = −19→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0424P)² + 0.6208P] where P = (F_o² + 2F_c²)/3
3992 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
S3	−0.11155 (5)	0.39341 (3)	0.39288 (3)	0.04084 (12)
S2	0.14706 (5)	0.19374 (3)	0.16270 (3)	0.04125 (12)
S1	0.34529 (6)	0.24704 (5)	0.36726 (3)	0.05848 (15)
O1	0.00460 (15)	0.32824 (10)	0.26734 (10)	0.0505 (3)
N3	−0.14307 (15)	0.20161 (10)	0.46198 (10)	0.0387 (3)
N1	0.37483 (17)	0.30273 (14)	0.20291 (11)	0.0504 (4)
N2	−0.02961 (10)	0.18869 (7)	0.35648 (7)	0.0398 (3)
H3	−0.0250	0.1209	0.3715	0.060*
C15	−0.19188 (10)	0.38955 (7)	0.47513 (7)	0.0390 (3)
C14	−0.24377 (10)	0.47707 (7)	0.51145 (7)	0.0524 (4)
H14	−0.2375	0.5497	0.4927	0.063*
C13	−0.3046 (2)	0.45284 (17)	0.57595 (18)	0.0621 (5)
H13	−0.3404	0.5099	0.6008	0.075*
C12	−0.3132 (2)	0.34427 (18)	0.60443 (17)	0.0607 (5)
H12	−0.3539	0.3300	0.6486	0.073*
C11	−0.2626 (2)	0.25758 (15)	0.56845 (15)	0.0506 (4)
H11	−0.2696	0.1852	0.5874	0.061*
C10	−0.20087 (17)	0.28022 (13)	0.50311 (12)	0.0381 (3)
C9	−0.09440 (16)	0.24949 (12)	0.40459 (11)	0.0344 (3)
C8	0.01508 (18)	0.23052 (13)	0.28907 (12)	0.0389 (3)
C7	0.0712 (2)	0.14189 (14)	0.24244 (13)	0.0450 (4)
H7A	−0.0025	0.0920	0.2054	0.054*
H7B	0.1392	0.0992	0.2943	0.054*
C6	0.30123 (18)	0.25403 (13)	0.24634 (12)	0.0401 (3)
C1	0.3334 (2)	0.31304 (17)	0.09552 (13)	0.0524 (5)
H1A	0.2466	0.2758	0.0618	0.063*
H1B	0.4010	0.2776	0.0763	0.063*
C2	0.3200 (2)	0.43266 (18)	0.06582 (15)	0.0607 (5)
H2A	0.2454	0.4658	0.0785	0.073*
H2B	0.2983	0.4380	−0.0042	0.073*
C3	0.4502 (3)	0.4956 (2)	0.1215 (2)	0.0794 (7)
H3A	0.4357	0.5738	0.1057	0.095*
H3B	0.5218	0.4697	0.1016	0.095*
C4	0.4948 (3)	0.4796 (2)	0.23209 (18)	0.0701 (6)
H4A	0.5832	0.5144	0.2661	0.084*
H4B	0.4295	0.5156	0.2534	0.084*
C5	0.5044 (2)	0.3595 (2)	0.25880 (17)	0.0632 (5)
H5A	0.5774	0.3253	0.2449	0.076*
H5B	0.5261	0.3520	0.3287	0.076*
O2	0.99835 (17)	0.03537 (10)	0.61071 (10)	0.0591 (4)
H2'A	0.9501	0.0735	0.5538	0.089*
H2'B	1.0111	0.0822	0.6617	0.089*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S3	0.0527 (3)	0.02621 (18)	0.0499 (2)	0.00354 (15)	0.0270 (2)	0.00531 (15)
S2	0.0520 (3)	0.0395 (2)	0.0354 (2)	−0.00204 (17)	0.02063 (18)	−0.00248 (15)
S1	0.0800 (4)	0.0582 (3)	0.0310 (2)	0.0053 (2)	0.0152 (2)	0.00416 (19)
O1	0.0772 (9)	0.0309 (6)	0.0565 (8)	0.0079 (6)	0.0403 (7)	0.0086 (5)
N3	0.0505 (8)	0.0279 (6)	0.0419 (7)	−0.0021 (5)	0.0225 (6)	0.0002 (5)
N1	0.0531 (9)	0.0581 (9)	0.0363 (7)	−0.0110 (7)	0.0135 (7)	0.0000 (7)
N2	0.0581 (9)	0.0250 (6)	0.0431 (7)	0.0033 (6)	0.0273 (7)	0.0030 (5)
C15	0.0415 (8)	0.0336 (8)	0.0442 (8)	0.0010 (6)	0.0192 (7)	0.0000 (6)
C14	0.0612 (11)	0.0352 (8)	0.0684 (12)	0.0057 (8)	0.0336 (10)	−0.0015 (8)
C13	0.0706 (13)	0.0503 (11)	0.0828 (15)	0.0061 (9)	0.0490 (12)	−0.0094 (10)
C12	0.0674 (13)	0.0575 (12)	0.0762 (14)	−0.0045 (10)	0.0487 (12)	−0.0074 (10)
C11	0.0603 (11)	0.0418 (9)	0.0611 (11)	−0.0072 (8)	0.0362 (10)	−0.0022 (8)
C10	0.0407 (8)	0.0330 (7)	0.0426 (8)	−0.0021 (6)	0.0185 (7)	−0.0021 (6)
C9	0.0405 (8)	0.0261 (7)	0.0359 (7)	0.0006 (6)	0.0144 (6)	0.0010 (5)
C8	0.0495 (9)	0.0318 (8)	0.0386 (8)	0.0030 (6)	0.0209 (7)	0.0021 (6)
C7	0.0632 (11)	0.0318 (8)	0.0496 (9)	0.0011 (7)	0.0325 (9)	0.0010 (7)
C6	0.0515 (9)	0.0328 (7)	0.0343 (8)	0.0058 (7)	0.0151 (7)	0.0012 (6)
C1	0.0619 (12)	0.0603 (11)	0.0391 (9)	−0.0108 (9)	0.0243 (8)	−0.0040 (8)
C2	0.0705 (14)	0.0633 (13)	0.0498 (11)	0.0025 (10)	0.0252 (10)	0.0052 (9)
C3	0.0941 (19)	0.0622 (14)	0.0802 (16)	−0.0202 (13)	0.0324 (14)	0.0070 (12)
C4	0.0686 (14)	0.0641 (13)	0.0749 (15)	−0.0181 (11)	0.0252 (12)	−0.0150 (12)
C5	0.0502 (11)	0.0731 (14)	0.0565 (12)	−0.0111 (10)	0.0103 (9)	−0.0025 (11)
O2	0.1018 (11)	0.0269 (6)	0.0487 (7)	0.0058 (6)	0.0297 (7)	0.0001 (5)

S3—C15	1.7395 (10)	C11—C10	1.392 (2)
S3—C9	1.7486 (15)	C11—H11	0.9300
S2—C6	1.7757 (18)	C8—C7	1.517 (2)
S2—C7	1.7828 (17)	C7—H7A	0.9700
S1—C6	1.6624 (16)	C7—H7B	0.9700
O1—C8	1.2163 (19)	C1—C2	1.500 (3)
N3—C9	1.291 (2)	C1—H1A	0.9700
N3—C10	1.394 (2)	C1—H1B	0.9700
N1—C6	1.329 (2)	C2—C3	1.508 (3)
N1—C5	1.468 (3)	C2—H2A	0.9700
N1—C1	1.477 (2)	C2—H2B	0.9700
N2—C8	1.3586 (18)	C3—C4	1.525 (3)
N2—C9	1.3799 (17)	C3—H3A	0.9700
N2—H3	0.8445	C3—H3B	0.9700
C15—C14	1.3936	C4—C5	1.496 (3)
C15—C10	1.3978 (18)	C4—H4A	0.9700
C14—C13	1.377 (2)	C4—H4B	0.9700
C14—H14	0.9300	C5—H5A	0.9700
C13—C12	1.391 (3)	C5—H5B	0.9700
C13—H13	0.9300	O2—H2'A	0.9186
C12—C11	1.376 (3)	O2—H2'B	0.9083
C12—H12	0.9300

C15—S3—C9	87.99 (6)	S2—C7—H7B	108.6
C6—S2—C7	102.54 (8)	H7A—C7—H7B	107.6
C9—N3—C10	109.94 (13)	N1—C6—S1	124.85 (14)
C6—N1—C5	122.35 (16)	N1—C6—S2	113.75 (12)
C6—N1—C1	124.96 (15)	S1—C6—S2	121.40 (10)
C5—N1—C1	112.56 (16)	N1—C1—C2	110.48 (16)
C8—N2—C9	124.72 (11)	N1—C1—H1A	109.6
C8—N2—H3	123.5	C2—C1—H1A	109.6
C9—N2—H3	111.7	N1—C1—H1B	109.6
C14—C15—C10	121.23 (8)	C2—C1—H1B	109.6
C14—C15—S3	128.8	H1A—C1—H1B	108.1
C10—C15—S3	109.98 (9)	C1—C2—C3	111.35 (19)
C13—C14—C15	118.06 (9)	C1—C2—H2A	109.4
C13—C14—H14	121.0	C3—C2—H2A	109.4
C15—C14—H14	121.0	C1—C2—H2B	109.4
C14—C13—C12	120.96 (16)	C3—C2—H2B	109.4
C14—C13—H13	119.5	H2A—C2—H2B	108.0
C12—C13—H13	119.5	C2—C3—C4	110.69 (19)
C11—C12—C13	121.18 (18)	C2—C3—H3A	109.5
C11—C12—H12	119.4	C4—C3—H3A	109.5
C13—C12—H12	119.4	C2—C3—H3B	109.5
C12—C11—C10	118.79 (17)	C4—C3—H3B	109.5
C12—C11—H11	120.6	H3A—C3—H3B	108.1
C10—C11—H11	120.6	C5—C4—C3	111.4 (2)
C11—C10—N3	125.33 (15)	C5—C4—H4A	109.3
C11—C10—C15	119.77 (14)	C3—C4—H4A	109.3
N3—C10—C15	114.89 (13)	C5—C4—H4B	109.3
N3—C9—N2	120.70 (13)	C3—C4—H4B	109.3
N3—C9—S3	117.19 (12)	H4A—C4—H4B	108.0
N2—C9—S3	122.09 (10)	N1—C5—C4	110.63 (18)
O1—C8—N2	122.14 (14)	N1—C5—H5A	109.5
O1—C8—C7	125.17 (15)	C4—C5—H5A	109.5
N2—C8—C7	112.63 (13)	N1—C5—H5B	109.5
C8—C7—S2	114.45 (12)	C4—C5—H5B	109.5
C8—C7—H7A	108.6	H5A—C5—H5B	108.1
S2—C7—H7A	108.6	H2'A—O2—H2'B	107.2
C8—C7—H7B	108.6

C9—S3—C15—C14	179.51 (6)	C15—S3—C9—N2	−178.26 (14)
C9—S3—C15—C10	−0.94 (11)	C9—N2—C8—O1	2.2 (3)
C10—C15—C14—C13	−0.05 (14)	C9—N2—C8—C7	−175.06 (14)
S3—C15—C14—C13	179.45 (15)	O1—C8—C7—S2	8.9 (3)
C15—C14—C13—C12	0.4 (3)	N2—C8—C7—S2	−173.96 (12)
C14—C13—C12—C11	−0.7 (4)	C6—S2—C7—C8	71.97 (15)
C13—C12—C11—C10	0.6 (3)	C5—N1—C6—S1	−1.7 (3)
C12—C11—C10—N3	178.85 (19)	C1—N1—C6—S1	−177.38 (15)
C12—C11—C10—C15	−0.3 (3)	C5—N1—C6—S2	178.72 (16)
C9—N3—C10—C11	−179.96 (17)	C1—N1—C6—S2	3.1 (2)
C9—N3—C10—C15	−0.8 (2)	C7—S2—C6—N1	−177.71 (13)
C14—C15—C10—C11	0.00 (19)	C7—S2—C6—S1	2.73 (12)
S3—C15—C10—C11	−179.59 (14)	C6—N1—C1—C2	118.0 (2)
C14—C15—C10—N3	−179.20 (9)	C5—N1—C1—C2	−58.0 (2)
S3—C15—C10—N3	1.21 (17)	N1—C1—C2—C3	55.5 (2)
C10—N3—C9—N2	178.87 (14)	C1—C2—C3—C4	−53.5 (3)
C10—N3—C9—S3	0.03 (19)	C2—C3—C4—C5	53.3 (3)
C8—N2—C9—N3	174.61 (15)	C6—N1—C5—C4	−118.4 (2)
C8—N2—C9—S3	−6.6 (2)	C1—N1—C5—C4	57.7 (2)
C15—S3—C9—N3	0.55 (13)	C3—C4—C5—N1	−54.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3···O2ⁱ	0.84	1.91	2.745 (2)	170
O2—H2'A···N3ⁱⁱ	0.92	2.04	2.920 (2)	160
O2—H2'B···O1ⁱⁱⁱ	0.91	1.92	2.821 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3⋯O2ⁱ	0.84	1.91	2.745 (2)	170
O2—H2′A⋯N3ⁱⁱ	0.92	2.04	2.920 (2)	160
O2—H2′B⋯O1ⁱⁱⁱ	0.91	1.92	2.821 (2)	169

Symmetry codes: (i) ; (ii) ; (iii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. New 4-thiazolidinones of nicotinic acid with 2-Amino-6-methylbenzothiazole and their biological activity.

Authors: Navin B Patel; Faiyazalam M Shaikh
Journal: Sci Pharm Date: 2010-10-24

2 in total