Crystal structure of 4-(2,2-di-methyl-propanamido)-pyridin-3-yl N,N-diiso-propyl-dithio-carbamate.

In the title compound, C17H27N3OS2, the amide group is approximately coplanar with the pyridine ring [dihedral angle = 1.6 (1)°], whereas the di-thio-carbamate 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 mol-ecules into inversion dimers.

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 ▶).

Experimental

Crystal data

C17H27N3OS2

M = 353.53

Triclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.211

S = 1.16

3779 reflections

215 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814019321/xu5816sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S1600536814019321/xu5816fig1.tif

The symmetric unit of the title compound with atom labels and 50% probability displacement ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S1600536814019321/xu5816fig2.tif

Packing in the crystal structure showing C—H⋯O contacts as dotted lines with hydrogen atoms omitted for clarity.

CCDC reference: 1021242

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H27N3OS2	Z = 2
Mr = 353.53	F(000) = 380
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1014P)2 + 0.897P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max < 0.001
3779 reflections	Δρmax = 0.39 e Å−3
215 parameters	Δρmin = −0.29 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.

	x	y	z	Uiso*/Ueq
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)

	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)

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

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

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) .