Crystal structure of 4-(2,2-di­methyl­propanamido)­pyridin-3-yl N,N-diiso­propyl­dithio­carbamate

El-Hiti, G.A.; Smith, K.; Hegazy, A.S.; Baashen, M.; Kariuki, B.M.

doi:10.1107/S1600536814019321

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1069-o1070

doi:10.1107/S1600536814019321

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Crystal structure of 4-(2,2-dimethylpropanamido)pyridin-3-yl N,N-diisopropyldithiocarbamate

Gamal A. El-Hiti,^a ^* Keith Smith,^b Amany S. Hegazy,^b Mohammed Baashen ^c and Benson M. Kariuki ^b ^*

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales, and ^cCriminal Evidence, Ministry of Interior, Riyadh 11632, PO Box 86985, Saudi Arabia
^*Correspondence e-mail: gelhiti@ksu.edu.s, kariukib@cardiff.ac.uk

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 20 August 2014; accepted 26 August 2014; online 30 August 2014)

In the title compound, C₁₇H₂₇N₃OS₂, the amide group is approximately coplanar with the pyridine ring [dihedral angle = 1.6 (1)°], whereas the dithiocarbamate group is nearly perpendicular to the pyridine ring [dihedral angle = 76.7 (1)°]. In the crystal, pairs of weak C—H⋯O hydrogen bonds link the molecules into inversion dimers.

Keywords: crystal structure; dithiocarbamate; pyridine derivatives; hydrogen bonding.

CCDC reference: 1021242

1. Related literature

For background to pyridine derivatives, see: Joule & Mills (2000 ); Smith et al. (1999 ). For the synthesis of the title compound, see: Smith et al. (1988 ). For spectroscopic data for this compound, see: Smith et al. (1994 ). For routes to modify the pyridine ring, see: El-Hiti (2003 ); Turner (1983 ). For crystal structures of related compounds, see: El-Hiti et al. (2014 ); Koch et al. (2008 ); Mazik & Sicking (2004 ).

2. Experimental

2.1. Crystal data

C₁₇H₂₇N₃OS₂
M_r = 353.53
Triclinic, $[P \overline 1]$
a = 7.9776 (7) Å
b = 9.5412 (9) Å
c = 13.0541 (14) Å
α = 83.099 (8)°
β = 83.227 (8)°
γ = 84.608 (7)°
V = 976.33 (17) Å³
Z = 2
Cu Kα radiation
μ = 2.52 mm⁻¹
T = 293 K
0.36 × 0.24 × 0.19 mm

2.2. Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ) T_min = 0.662, T_max = 1.000
6616 measured reflections
3779 independent reflections
3391 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.211
S = 1.16
3779 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.54	3.447 (5)	164
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1021242

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814019321/xu5816sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019321/xu5816Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814019321/xu5816Isup3.cml

checkCIF report

Chemical context top

Pyridine derivatives are important compounds (Joule & Mills, 2000) and various substituted derivatives can be synthesized via lithiation and subsequent reaction with electrophiles (Turner, 1983). During research focused on synthesis of novel substituted pyridines (El-Hiti, 2003; Smith et al., 1999) we have synthesized the title compound in high yield. For the X-ray structures for related compounds, see: El-Hiti et al., 2014; Koch et al., 2008; Mazik & Sicking, 2004.

Structural commentary top

In the molecule of the title compound, C₁₇H₂₇N₃OS₂, (Fig. 1), the pyridine group is almost co-planar (1.6 (1)^o) to the amide group whereas the angle to the carbamodithioate is 76.7 (1)^o. No strong hydrogen bonding interactions occur, with pairs of molecules being linked by pairs of C—H..O contacts (Fig. 2). The molecular pairs are stacked along [010] leading to a structure in which the t-butyl groups form bilayers parallel to the ab plane.

Synthesis and crystallization top

4-Pivalamidopyridin-3-yl diisopropylcarbamodithioate was obtained in 93% yield from double lithiation of 4-(pivaloylamino)pyridin-3-yl with n-butyllithium at –78 to 0°C in anhydrous THF under nitrogen followed by reaction with tetraisopropylthiuram disulfide (Smith et al., 1988, 1994). Crystallization from ethyl acetate gave colorless crystals of the title compound. The spectroscopic data of the title compound, including NMR and low and high resolution mass spectra, were consistent with those reported (Smith et al., 1994).

Refinement details top

H atoms were positioned geometrically and refined using a riding model, with U_iso(H) constrained to be 1.2 times U_eq for the bonded atom except for methyl groups where it was 1.5 times with free rotation about the C—C bond.

Related literature top

For background to pyridine derivatives, see: Joule & Mills (2000); Smith et al. (1999). For the synthesis of the title compound, see: Smith et al. (1988). For spectroscopic data for this compound, see: Smith et al. (1994). For routes to modify the pyridine ring, see: El-Hiti (2003); Turner (1983). For crystal structures of related compounds, see: El-Hiti et al. (2014); Koch et al. (2008); Mazik & Sicking (2004).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

Figures top

	Fig. 1. The symmetric unit of the title compound with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Packing in the crystal structure showing C—H···O contacts as dotted lines with hydrogen atoms omitted for clarity.

4-(2,2-Dimethylpropanamido)pyridin-3-yl N,N-diisopropyldithiocarbamate top

Crystal data top

C₁₇H₂₇N₃OS₂	Z = 2
M_r = 353.53	F(000) = 380
Triclinic, P1	D_x = 1.203 Mg m⁻³
a = 7.9776 (7) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.5412 (9) Å	Cell parameters from 3458 reflections
c = 13.0541 (14) Å	θ = 4.7–73.3°
α = 83.099 (8)°	µ = 2.52 mm⁻¹
β = 83.227 (8)°	T = 293 K
γ = 84.608 (7)°	Block, colourless
V = 976.33 (17) Å³	0.36 × 0.24 × 0.19 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3391 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	R_int = 0.021
ω scans	θ_max = 73.5°, θ_min = 4.7°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −9→9
T_min = 0.662, T_max = 1.000	k = −11→11
6616 measured reflections	l = −11→16
3779 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.211	w = 1/[σ²(F_o²) + (0.1014P)² + 0.897P] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max < 0.001
3779 reflections	Δρ_max = 0.39 e Å⁻³
215 parameters	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₂₇N₃OS₂	γ = 84.608 (7)°
M_r = 353.53	V = 976.33 (17) Å³
Triclinic, P1	Z = 2
a = 7.9776 (7) Å	Cu Kα radiation
b = 9.5412 (9) Å	µ = 2.52 mm⁻¹
c = 13.0541 (14) Å	T = 293 K
α = 83.099 (8)°	0.36 × 0.24 × 0.19 mm
β = 83.227 (8)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3779 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	3391 reflections with I > 2σ(I)
T_min = 0.662, T_max = 1.000	R_int = 0.021
6616 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.16	Δρ_max = 0.39 e Å⁻³
3779 reflections	Δρ_min = −0.29 e Å⁻³
215 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.0193 (4)	0.7422 (4)	0.4668 (2)	0.0459 (7)
C2	0.1318 (4)	0.6291 (3)	0.4352 (2)	0.0452 (7)
C3	0.2680 (5)	0.5875 (4)	0.4929 (3)	0.0537 (8)
H3	0.3449	0.5121	0.4759	0.064*
C4	0.2866 (5)	0.6596 (5)	0.5752 (3)	0.0635 (10)
H4	0.3792	0.6311	0.6120	0.076*
C5	0.0505 (5)	0.8057 (4)	0.5520 (3)	0.0565 (8)
H5	−0.0253	0.8798	0.5727	0.068*
C6	−0.1194 (4)	0.8903 (3)	0.2919 (2)	0.0419 (6)
C7	−0.2165 (5)	1.0250 (5)	0.1370 (3)	0.0658 (10)
H7	−0.0963	1.0426	0.1293	0.079*
C8	−0.3150 (9)	1.1680 (6)	0.1370 (5)	0.0960 (17)
H8A	−0.4341	1.1560	0.1441	0.144*
H8B	−0.2847	1.2250	0.0729	0.144*
H8C	−0.2889	1.2141	0.1939	0.144*
C9	−0.2421 (9)	0.9459 (7)	0.0484 (4)	0.1004 (18)
H9A	−0.1624	0.8641	0.0467	0.151*
H9B	−0.2250	1.0063	−0.0156	0.151*
H9C	−0.3552	0.9165	0.0573	0.151*
C10	−0.4303 (4)	0.9068 (4)	0.2679 (3)	0.0534 (8)
H10	−0.4906	0.9553	0.2108	0.064*
C11	−0.4589 (6)	0.7522 (5)	0.2694 (4)	0.0733 (12)
H11A	−0.4032	0.7174	0.2071	0.110*
H11B	−0.5781	0.7418	0.2736	0.110*
H11C	−0.4135	0.6990	0.3285	0.110*
C12	−0.5115 (5)	0.9746 (5)	0.3641 (3)	0.0704 (11)
H12A	−0.4714	0.9220	0.4250	0.106*
H12B	−0.6324	0.9739	0.3684	0.106*
H12C	−0.4816	1.0705	0.3592	0.106*
C13	0.2026 (5)	0.4709 (4)	0.2956 (3)	0.0554 (8)
C14	0.1560 (6)	0.4522 (4)	0.1882 (3)	0.0613 (9)
C15	−0.0198 (8)	0.5172 (7)	0.1668 (4)	0.0987 (18)
H15A	−0.1028	0.4767	0.2183	0.148*
H15B	−0.0419	0.4983	0.0992	0.148*
H15C	−0.0255	0.6177	0.1693	0.148*
C16	0.2920 (10)	0.5217 (8)	0.1114 (4)	0.113 (2)
H16A	0.2806	0.5005	0.0427	0.169*
H16B	0.4020	0.4859	0.1301	0.169*
H16C	0.2785	0.6225	0.1134	0.169*
C17	0.1623 (8)	0.2942 (5)	0.1788 (4)	0.0875 (15)
H17A	0.0784	0.2520	0.2289	0.131*
H17B	0.2725	0.2507	0.1914	0.131*
H17C	0.1399	0.2803	0.1102	0.131*
N1	0.1823 (5)	0.7673 (4)	0.6064 (3)	0.0678 (9)
N2	0.1026 (4)	0.5683 (3)	0.3481 (2)	0.0523 (7)
H2	0.0079	0.5961	0.3239	0.063*
N3	−0.2495 (3)	0.9371 (3)	0.2384 (2)	0.0467 (6)
O2	0.3244 (5)	0.4055 (4)	0.3306 (3)	0.0946 (12)
S1	−0.17473 (10)	0.79230 (10)	0.41574 (6)	0.0518 (3)
S2	0.08414 (10)	0.91374 (10)	0.25296 (7)	0.0535 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0432 (16)	0.0523 (17)	0.0417 (15)	−0.0037 (13)	−0.0063 (12)	−0.0018 (13)
C2	0.0450 (17)	0.0487 (17)	0.0425 (15)	−0.0054 (13)	−0.0070 (13)	−0.0038 (12)
C3	0.0479 (19)	0.061 (2)	0.0522 (18)	0.0012 (15)	−0.0112 (15)	−0.0045 (15)
C4	0.055 (2)	0.083 (3)	0.055 (2)	−0.0003 (19)	−0.0214 (17)	−0.0078 (18)
C5	0.058 (2)	0.064 (2)	0.0489 (18)	0.0016 (16)	−0.0091 (15)	−0.0113 (15)
C6	0.0387 (15)	0.0442 (15)	0.0439 (15)	−0.0038 (12)	−0.0051 (12)	−0.0079 (12)
C7	0.053 (2)	0.087 (3)	0.055 (2)	−0.0067 (19)	−0.0119 (16)	0.0123 (19)
C8	0.117 (5)	0.075 (3)	0.093 (4)	−0.006 (3)	−0.029 (3)	0.017 (3)
C9	0.125 (5)	0.124 (5)	0.048 (2)	0.006 (4)	−0.005 (3)	−0.007 (3)
C10	0.0340 (16)	0.072 (2)	0.0564 (19)	−0.0040 (15)	−0.0084 (14)	−0.0128 (16)
C11	0.054 (2)	0.082 (3)	0.090 (3)	−0.021 (2)	−0.011 (2)	−0.019 (2)
C12	0.046 (2)	0.097 (3)	0.070 (2)	0.007 (2)	−0.0047 (17)	−0.025 (2)
C13	0.056 (2)	0.0511 (18)	0.061 (2)	0.0001 (15)	−0.0111 (16)	−0.0131 (15)
C14	0.072 (2)	0.059 (2)	0.055 (2)	−0.0088 (18)	−0.0056 (18)	−0.0155 (16)
C15	0.111 (4)	0.120 (4)	0.076 (3)	0.014 (3)	−0.046 (3)	−0.040 (3)
C16	0.142 (6)	0.136 (5)	0.066 (3)	−0.069 (5)	0.002 (3)	−0.005 (3)
C17	0.111 (4)	0.071 (3)	0.087 (3)	−0.011 (3)	−0.009 (3)	−0.033 (2)
N1	0.068 (2)	0.084 (2)	0.0559 (18)	−0.0008 (18)	−0.0189 (16)	−0.0206 (16)
N2	0.0496 (16)	0.0579 (16)	0.0520 (15)	0.0043 (13)	−0.0158 (12)	−0.0134 (13)
N3	0.0377 (13)	0.0586 (16)	0.0447 (14)	−0.0029 (11)	−0.0089 (11)	−0.0055 (11)
O2	0.090 (2)	0.098 (2)	0.102 (2)	0.042 (2)	−0.041 (2)	−0.045 (2)
S1	0.0388 (4)	0.0662 (5)	0.0473 (5)	−0.0015 (3)	−0.0035 (3)	0.0026 (4)
S2	0.0376 (4)	0.0614 (5)	0.0600 (5)	−0.0087 (3)	−0.0049 (3)	0.0029 (4)

Geometric parameters (Å, º) top

C1—C5	1.386 (5)	C10—C11	1.511 (6)
C1—C2	1.406 (5)	C10—C12	1.530 (5)
C1—S1	1.760 (3)	C10—H10	0.9800
C2—N2	1.390 (4)	C11—H11A	0.9600
C2—C3	1.395 (5)	C11—H11B	0.9600
C3—C4	1.373 (5)	C11—H11C	0.9600
C3—H3	0.9300	C12—H12A	0.9600
C4—N1	1.332 (5)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—N1	1.336 (5)	C13—O2	1.210 (5)
C5—H5	0.9300	C13—N2	1.361 (5)
C6—N3	1.331 (4)	C13—C14	1.527 (5)
C6—S2	1.671 (3)	C14—C15	1.522 (7)
C6—S1	1.797 (3)	C14—C17	1.523 (6)
C7—N3	1.489 (5)	C14—C16	1.530 (7)
C7—C9	1.498 (7)	C15—H15A	0.9600
C7—C8	1.509 (7)	C15—H15B	0.9600
C7—H7	0.9800	C15—H15C	0.9600
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C9—H9A	0.9600	C17—H17A	0.9600
C9—H9B	0.9600	C17—H17B	0.9600
C9—H9C	0.9600	C17—H17C	0.9600
C10—N3	1.494 (4)	N2—H2	0.8600

C5—C1—C2	118.5 (3)	C10—C11—H11C	109.5
C5—C1—S1	117.4 (3)	H11A—C11—H11C	109.5
C2—C1—S1	123.5 (2)	H11B—C11—H11C	109.5
N2—C2—C3	124.4 (3)	C10—C12—H12A	109.5
N2—C2—C1	118.3 (3)	C10—C12—H12B	109.5
C3—C2—C1	117.3 (3)	H12A—C12—H12B	109.5
C4—C3—C2	118.8 (3)	C10—C12—H12C	109.5
C4—C3—H3	120.6	H12A—C12—H12C	109.5
C2—C3—H3	120.6	H12B—C12—H12C	109.5
N1—C4—C3	125.0 (3)	O2—C13—N2	122.1 (4)
N1—C4—H4	117.5	O2—C13—C14	121.6 (4)
C3—C4—H4	117.5	N2—C13—C14	116.2 (3)
N1—C5—C1	124.3 (4)	C15—C14—C17	107.8 (4)
N1—C5—H5	117.9	C15—C14—C13	114.1 (3)
C1—C5—H5	117.9	C17—C14—C13	108.3 (4)
N3—C6—S2	125.8 (2)	C15—C14—C16	110.6 (5)
N3—C6—S1	115.0 (2)	C17—C14—C16	110.7 (4)
S2—C6—S1	119.17 (18)	C13—C14—C16	105.3 (4)
N3—C7—C9	111.2 (4)	C14—C15—H15A	109.5
N3—C7—C8	111.3 (4)	C14—C15—H15B	109.5
C9—C7—C8	114.1 (4)	H15A—C15—H15B	109.5
N3—C7—H7	106.6	C14—C15—H15C	109.5
C9—C7—H7	106.6	H15A—C15—H15C	109.5
C8—C7—H7	106.6	H15B—C15—H15C	109.5
C7—C8—H8A	109.5	C14—C16—H16A	109.5
C7—C8—H8B	109.5	C14—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C7—C8—H8C	109.5	C14—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C7—C9—H9A	109.5	C14—C17—H17A	109.5
C7—C9—H9B	109.5	C14—C17—H17B	109.5
H9A—C9—H9B	109.5	H17A—C17—H17B	109.5
C7—C9—H9C	109.5	C14—C17—H17C	109.5
H9A—C9—H9C	109.5	H17A—C17—H17C	109.5
H9B—C9—H9C	109.5	H17B—C17—H17C	109.5
N3—C10—C11	113.1 (3)	C4—N1—C5	116.0 (3)
N3—C10—C12	113.3 (3)	C13—N2—C2	129.2 (3)
C11—C10—C12	114.6 (4)	C13—N2—H2	115.4
N3—C10—H10	104.9	C2—N2—H2	115.4
C11—C10—H10	104.9	C6—N3—C7	118.8 (3)
C12—C10—H10	104.9	C6—N3—C10	126.5 (3)
C10—C11—H11A	109.5	C7—N3—C10	114.7 (3)
C10—C11—H11B	109.5	C1—S1—C6	104.98 (15)
H11A—C11—H11B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.54	3.447 (5)	164

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.54	3.447 (5)	164

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors would like to extend their appreciation to the Cornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, for funding this research.

References

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1069-o1070

doi:10.1107/S1600536814019321

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

Crystal structure of 4-(2,2-di­methyl­propanamido)­pyridin-3-yl N,N-diiso­propyl­di­thio­carbamate

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 4-(2,2-dimethylpropanamido)pyridin-3-yl N,N-diisopropyldithiocarbamate