Literature DB >> 21583884

Dipyridinium 2,2'-dithio-dinicotinate.

Wagee A Yehye¹, Azhar Ariffin, Noorsaadah Abdul Rahman, Seik Weng Ng.

Abstract

The dianion of the title salt, 2C(5)H(6)N(+)·C(12)H(6)N(2)O(4)S(2) (2-), lies on a special position of 2 site symmetry that relates one thio-nicotinate part to the other, and the dihedral angle between the niotinate planes is 89.2 (2)°. The pyridinium cations are hydrogen bonded to the carboxyl-ate group by way of N-H⋯O links.

Entities: Chemical Disease Species

Year: 2009 PMID： 21583884 PMCID： PMC2977748 DOI： 10.1107/S1600536809013543

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

Related literature

The structure is a non-merohedral twin; for the program to model twinned crystal structures, see: Spek (2003 ▶). For 1,1′-dithio-2,2′-dinicotinic acid, see: Zhu et al. (2002 ▶). For the methyl, ethyl and n-butyl esters, see: Cindrić et al. (2001 ▶); Toma et al. (2004 ▶).

Experimental

Crystal data

2C5H6N+·C12H6N2O4S2 2− M = 466.52 Monoclinic, a = 7.9621 (3) Å b = 12.3354 (4) Å c = 21.5057 (8) Å β = 95.917 (2)° V = 2100.9 (1) Å3 Z = 4 Mo Kα radiation μ = 0.29 mm−1 T = 123 K 0.28 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.923, T max = 0.977 6726 measured reflections 1855 independent reflections 1496 reflections with I > 2σ(I) R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.092 wR(F 2) = 0.269 S = 1.59 1855 reflections 146 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.57 e Å−3 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013543/si2170sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013543/si2170Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C₅H₆N⁺·C₁₂H₆N₂O₄S₂²⁻	F(000) = 968
M_r = 466.52	D_x = 1.475 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1585 reflections
a = 7.9621 (3) Å	θ = 3.1–24.0°
b = 12.3354 (4) Å	µ = 0.29 mm⁻¹
c = 21.5057 (8) Å	T = 123 K
β = 95.917 (2)°	Chip, light yellow
V = 2100.9 (1) Å³	0.28 × 0.16 × 0.08 mm
Z = 4

Bruker SMART APEX diffractometer	1855 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
graphite	R_int = 0.101
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.923, T_max = 0.977	k = −14→14
6726 measured reflections	l = −25→25

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.269	H-atom parameters constrained
S = 1.59	w = 1/[σ²(F_o²) + (0.1P)² + 5P] where P = (F_o² + 2F_c²)/3
1855 reflections	(Δ/σ)_max = 0.001
146 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

	x	y	z	U_iso*/U_eq
S1	0.5434 (2)	0.61088 (12)	0.29627 (7)	0.0213 (5)
O1	0.6450 (6)	0.6042 (4)	0.4204 (2)	0.0317 (12)
O2	0.5265 (6)	0.6888 (4)	0.4968 (2)	0.0336 (12)
N1	0.3073 (7)	0.7643 (4)	0.2874 (2)	0.0249 (12)
N2	0.7396 (7)	0.5816 (4)	0.5721 (3)	0.0278 (13)
H2	0.6690	0.6218	0.5478	0.033*
C1	0.2040 (9)	0.8378 (5)	0.3103 (3)	0.0299 (16)
H1	0.1300	0.8778	0.2814	0.036*
C2	0.1994 (8)	0.8583 (5)	0.3731 (3)	0.0271 (15)
H2A	0.1240	0.9102	0.3873	0.033*
C3	0.3092 (8)	0.8001 (5)	0.4142 (3)	0.0249 (14)
H3	0.3091	0.8116	0.4579	0.030*
C4	0.4190 (8)	0.7255 (5)	0.3929 (3)	0.0204 (13)
C5	0.4125 (8)	0.7097 (5)	0.3280 (3)	0.0191 (13)
C6	0.5418 (8)	0.6678 (5)	0.4383 (3)	0.0227 (14)
C7	0.7634 (9)	0.5987 (6)	0.6336 (3)	0.0311 (16)
H7	0.7030	0.6557	0.6510	0.037*
C8	0.8721 (9)	0.5368 (6)	0.6728 (3)	0.0342 (17)
H8	0.8862	0.5512	0.7164	0.041*
C9	0.9605 (9)	0.4535 (6)	0.6481 (3)	0.0325 (16)
H9	1.0335	0.4081	0.6744	0.039*
C10	0.9398 (10)	0.4379 (6)	0.5841 (3)	0.0329 (16)
H10	1.0030	0.3842	0.5651	0.039*
C11	0.8259 (9)	0.5018 (5)	0.5485 (3)	0.0280 (15)
H11	0.8078	0.4883	0.5049	0.034*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0232 (9)	0.0189 (8)	0.0212 (8)	0.0044 (6)	−0.0002 (6)	0.0000 (6)
O1	0.035 (3)	0.036 (3)	0.023 (2)	0.016 (2)	−0.003 (2)	−0.0003 (19)
O2	0.038 (3)	0.040 (3)	0.022 (2)	0.017 (2)	−0.002 (2)	0.000 (2)
N1	0.023 (3)	0.021 (3)	0.029 (3)	0.010 (2)	−0.003 (2)	0.000 (2)
N2	0.025 (3)	0.029 (3)	0.029 (3)	0.001 (2)	−0.003 (2)	0.000 (2)
C1	0.029 (4)	0.020 (3)	0.039 (4)	0.004 (3)	−0.003 (3)	0.001 (3)
C2	0.023 (3)	0.018 (3)	0.040 (4)	0.000 (3)	0.004 (3)	−0.003 (3)
C3	0.027 (3)	0.023 (3)	0.027 (3)	0.004 (3)	0.009 (3)	−0.001 (3)
C4	0.019 (3)	0.016 (3)	0.025 (3)	−0.003 (2)	−0.003 (3)	0.002 (2)
C5	0.020 (3)	0.018 (3)	0.019 (3)	0.000 (2)	0.003 (2)	0.003 (2)
C6	0.024 (3)	0.017 (3)	0.026 (3)	−0.001 (3)	−0.001 (3)	−0.001 (2)
C7	0.027 (4)	0.037 (4)	0.028 (4)	−0.002 (3)	−0.003 (3)	−0.006 (3)
C8	0.024 (4)	0.053 (5)	0.024 (3)	0.001 (3)	−0.005 (3)	−0.001 (3)
C9	0.021 (3)	0.037 (4)	0.038 (4)	−0.003 (3)	−0.005 (3)	0.004 (3)
C10	0.034 (4)	0.025 (3)	0.039 (4)	0.002 (3)	−0.002 (3)	−0.001 (3)
C11	0.028 (4)	0.029 (3)	0.027 (3)	0.002 (3)	0.002 (3)	−0.002 (3)

S1—C5	1.785 (6)	C3—C4	1.380 (9)
S1—S1ⁱ	2.038 (3)	C3—H3	0.9500
O1—C6	1.226 (8)	C4—C5	1.405 (9)
O2—C6	1.302 (8)	C4—C6	1.490 (8)
N1—C5	1.329 (8)	C7—C8	1.375 (10)
N1—C1	1.350 (8)	C7—H7	0.9500
N2—C11	1.330 (9)	C8—C9	1.383 (10)
N2—C7	1.333 (8)	C8—H8	0.9500
N2—H2	0.8800	C9—C10	1.384 (10)
C1—C2	1.376 (9)	C9—H9	0.9500
C1—H1	0.9500	C10—C11	1.372 (10)
C2—C3	1.380 (9)	C10—H10	0.9500
C2—H2A	0.9500	C11—H11	0.9500

C5—S1—S1ⁱ	102.7 (2)	C4—C5—S1	120.8 (5)
C5—N1—C1	117.8 (6)	O1—C6—O2	124.2 (6)
C11—N2—C7	117.9 (6)	O1—C6—C4	121.1 (6)
C11—N2—H2	121.0	O2—C6—C4	114.7 (5)
C7—N2—H2	121.0	N2—C7—C8	122.4 (7)
N1—C1—C2	124.0 (6)	N2—C7—H7	118.8
N1—C1—H1	118.0	C8—C7—H7	118.8
C2—C1—H1	118.0	C7—C8—C9	119.4 (7)
C1—C2—C3	117.0 (6)	C7—C8—H8	120.3
C1—C2—H2A	121.5	C9—C8—H8	120.3
C3—C2—H2A	121.5	C8—C9—C10	118.2 (6)
C4—C3—C2	121.0 (6)	C8—C9—H9	120.9
C4—C3—H3	119.5	C10—C9—H9	120.9
C2—C3—H3	119.5	C11—C10—C9	118.6 (7)
C3—C4—C5	117.6 (6)	C11—C10—H10	120.7
C3—C4—C6	119.8 (6)	C9—C10—H10	120.7
C5—C4—C6	122.6 (6)	N2—C11—C10	123.4 (6)
N1—C5—C4	122.5 (6)	N2—C11—H11	118.3
N1—C5—S1	116.7 (5)	C10—C11—H11	118.3

C5—N1—C1—C2	−1.0 (10)	S1ⁱ—S1—C5—C4	172.6 (5)
N1—C1—C2—C3	0.6 (10)	C3—C4—C6—O1	−177.2 (6)
C1—C2—C3—C4	0.5 (9)	C5—C4—C6—O1	0.9 (9)
C2—C3—C4—C5	−1.2 (9)	C3—C4—C6—O2	4.3 (8)
C2—C3—C4—C6	177.1 (6)	C5—C4—C6—O2	−177.5 (6)
C1—N1—C5—C4	0.2 (9)	C11—N2—C7—C8	−0.4 (10)
C1—N1—C5—S1	178.5 (5)	N2—C7—C8—C9	−0.1 (11)
C3—C4—C5—N1	0.9 (9)	C7—C8—C9—C10	2.1 (11)
C6—C4—C5—N1	−177.3 (5)	C8—C9—C10—C11	−3.5 (10)
C3—C4—C5—S1	−177.4 (5)	C7—N2—C11—C10	−1.2 (10)
C6—C4—C5—S1	4.4 (8)	C9—C10—C11—N2	3.2 (11)
S1ⁱ—S1—C5—N1	−5.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88	1.71	2.586 (7)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88	1.71	2.586 (7)	174

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