Literature DB >> 21200766

2-(4,6-Dimethyl-pyrimidin-2-ylsulfan-yl)-N-(4-methyl-pyridin-2-yl)acetamide.

Dong Liang¹, Li-Xing Gao, Yan Gao, Jing Xu, Wei Wang.

Abstract

The non-H atoms of the title mol-ecule, C(14)H(16)N(4)OS, are coplanar, with an r.m.s. deviation of 0.039 Å. The dihedral angle between the two aromatic rings is 2.4 (2)°. An intra-molecular C-H⋯O hydrogen bond is observed. The mol-ecules exist as N-H⋯N hydrogen-bonded centrosymmetric dimers.

Entities: CellLine Chemical Disease Gene

Year: 2007 PMID： 21200766 PMCID： PMC2915263 DOI： 10.1107/S1600536807064082

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

Related literature

For related literature, see: Koike et al. (1999 ▶).

Experimental

Crystal data

C14H16N4OS M = 288.37 Monoclinic, a = 5.1924 (19) Å b = 15.423 (5) Å c = 18.121 (6) Å β = 91.678 (6)° V = 1450.5 (9) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 293 (2) K 0.40 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.916, T max = 0.957 8084 measured reflections 2970 independent reflections 1582 reflections with I > 2σ(I) R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.144 S = 0.98 2970 reflections 184 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.23 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807064082/ci2528sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064082/ci2528Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₆N₄OS	F₀₀₀ = 608
M_r = 288.37	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 5.1924 (19) Å	Cell parameters from 1663 reflections
b = 15.423 (5) Å	θ = 2.6–22.2º
c = 18.121 (6) Å	µ = 0.22 mm⁻¹
β = 91.678 (6)º	T = 293 (2) K
V = 1450.5 (9) Å³	Plate, colourless
Z = 4	0.40 × 0.24 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	2970 independent reflections
Radiation source: fine-focus sealed tube	1582 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.060
T = 293(2) K	θ_max = 26.4º
φ and ω scans	θ_min = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −6→4
T_min = 0.916, T_max = 0.957	k = −17→19
8084 measured reflections	l = −22→22

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.144	w = 1/[σ²(F_o²) + (0.0718P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.004
2970 reflections	Δρ_max = 0.27 e Å⁻³
184 parameters	Δρ_min = −0.23 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.19772 (16)	0.06150 (5)	0.30190 (4)	0.0565 (3)
O1	0.4584 (4)	0.17627 (12)	0.39721 (11)	0.0629 (6)
C8	0.5502 (6)	0.10500 (16)	0.40685 (14)	0.0424 (7)
N3	0.7497 (4)	0.08705 (13)	0.45581 (11)	0.0437 (6)
H3A	0.7929	0.0334	0.4603	0.052*
N1	−0.0905 (5)	−0.02849 (15)	0.21206 (12)	0.0526 (6)
N2	0.2279 (4)	−0.11038 (14)	0.28121 (12)	0.0487 (6)
N4	1.0824 (5)	0.11059 (13)	0.54011 (12)	0.0471 (6)
C7	0.4517 (5)	0.02656 (16)	0.36422 (15)	0.0466 (7)
H7A	0.3873	−0.0166	0.3980	0.056*
H7B	0.5901	0.0008	0.3369	0.056*
C1	0.1057 (6)	−0.03772 (17)	0.26160 (15)	0.0464 (7)
C9	0.8914 (5)	0.14679 (15)	0.49939 (13)	0.0390 (7)
C10	0.8368 (6)	0.23511 (16)	0.50028 (15)	0.0493 (7)
H10	0.7006	0.2572	0.4716	0.059*
C3	−0.0551 (6)	−0.18068 (19)	0.19480 (16)	0.0566 (8)
H3	−0.1119	−0.2310	0.1712	0.068*
C12	1.1828 (6)	0.25295 (18)	0.58610 (17)	0.0580 (8)
H12	1.2871	0.2874	0.6167	0.070*
C4	0.1449 (6)	−0.18362 (18)	0.24637 (16)	0.0502 (7)
C2	−0.1703 (6)	−0.1016 (2)	0.17864 (15)	0.0535 (8)
C5	0.2828 (6)	−0.26511 (18)	0.26755 (19)	0.0677 (9)
H5A	0.4476	−0.2663	0.2449	0.102*
H5B	0.1828	−0.3142	0.2511	0.102*
H5C	0.3067	−0.2673	0.3202	0.102*
C13	1.2229 (6)	0.16531 (18)	0.58239 (17)	0.0611 (9)
H13	1.3570	0.1421	0.6112	0.073*
C6	−0.3885 (7)	−0.0931 (2)	0.12243 (18)	0.0747 (10)
H6A	−0.5028	−0.0478	0.1372	0.112*
H6B	−0.4812	−0.1469	0.1191	0.112*
H6C	−0.3205	−0.0792	0.0752	0.112*
C11	0.9856 (6)	0.28937 (17)	0.54384 (15)	0.0507 (8)
C14	0.9279 (7)	0.38546 (17)	0.54669 (19)	0.0782 (11)
H14A	0.8268	0.3977	0.5890	0.117*
H14B	0.8337	0.4023	0.5026	0.117*
H14C	1.0866	0.4173	0.5503	0.117*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0590 (5)	0.0408 (4)	0.0681 (5)	0.0027 (4)	−0.0256 (4)	−0.0038 (4)
O1	0.0813 (16)	0.0368 (11)	0.0683 (13)	0.0118 (10)	−0.0348 (12)	−0.0053 (9)
C8	0.0517 (18)	0.0305 (15)	0.0445 (16)	0.0044 (13)	−0.0055 (14)	−0.0006 (12)
N3	0.0501 (15)	0.0285 (11)	0.0516 (14)	0.0060 (10)	−0.0152 (12)	−0.0033 (10)
N1	0.0499 (16)	0.0553 (15)	0.0518 (15)	−0.0103 (12)	−0.0128 (12)	0.0042 (12)
N2	0.0498 (16)	0.0438 (14)	0.0521 (14)	−0.0044 (11)	−0.0070 (12)	−0.0049 (11)
N4	0.0469 (15)	0.0359 (13)	0.0574 (14)	0.0054 (11)	−0.0174 (12)	−0.0049 (11)
C7	0.0497 (18)	0.0393 (16)	0.0502 (17)	0.0008 (13)	−0.0118 (14)	−0.0047 (13)
C1	0.0471 (18)	0.0445 (17)	0.0476 (17)	−0.0084 (13)	−0.0029 (14)	0.0002 (13)
C9	0.0419 (17)	0.0334 (14)	0.0414 (15)	0.0019 (12)	−0.0031 (13)	−0.0014 (12)
C10	0.0582 (19)	0.0341 (15)	0.0546 (18)	0.0111 (13)	−0.0154 (15)	−0.0024 (13)
C3	0.060 (2)	0.0498 (19)	0.0594 (19)	−0.0169 (16)	−0.0021 (16)	−0.0065 (15)
C12	0.062 (2)	0.0379 (17)	0.072 (2)	−0.0005 (14)	−0.0252 (17)	−0.0088 (14)
C4	0.0496 (19)	0.0465 (17)	0.0544 (18)	−0.0109 (14)	−0.0015 (15)	−0.0074 (14)
C2	0.0496 (19)	0.063 (2)	0.0477 (18)	−0.0202 (16)	−0.0086 (15)	0.0012 (14)
C5	0.075 (2)	0.0444 (18)	0.083 (2)	−0.0057 (16)	−0.0081 (19)	−0.0105 (16)
C13	0.057 (2)	0.0455 (18)	0.079 (2)	0.0046 (15)	−0.0272 (17)	−0.0055 (15)
C6	0.071 (2)	0.081 (2)	0.070 (2)	−0.0275 (19)	−0.0276 (19)	0.0112 (18)
C11	0.062 (2)	0.0339 (15)	0.0554 (18)	0.0007 (14)	−0.0062 (16)	−0.0046 (13)
C14	0.104 (3)	0.0346 (17)	0.094 (3)	0.0064 (17)	−0.028 (2)	−0.0098 (16)

S1—C1	1.756 (3)	C3—C2	1.386 (4)
S1—C7	1.794 (3)	C3—H3	0.93
O1—C8	1.209 (3)	C12—C13	1.369 (4)
C8—N3	1.372 (3)	C12—C11	1.380 (4)
C8—C7	1.516 (3)	C12—H12	0.93
N3—C9	1.407 (3)	C4—C5	1.491 (4)
N3—H3A	0.86	C2—C6	1.507 (4)
N1—C2	1.340 (3)	C5—H5A	0.96
N1—C1	1.346 (3)	C5—H5B	0.96
N2—C1	1.331 (3)	C5—H5C	0.96
N2—C4	1.358 (3)	C13—H13	0.93
N4—C9	1.341 (3)	C6—H6A	0.96
N4—C13	1.341 (3)	C6—H6B	0.96
C7—H7A	0.97	C6—H6C	0.96
C7—H7B	0.97	C11—C14	1.513 (4)
C9—C10	1.391 (3)	C14—H14A	0.96
C10—C11	1.373 (4)	C14—H14B	0.96
C10—H10	0.93	C14—H14C	0.96
C3—C4	1.377 (4)

C1—S1—C7	100.72 (13)	N2—C4—C3	120.7 (3)
O1—C8—N3	124.3 (2)	N2—C4—C5	116.0 (3)
O1—C8—C7	121.8 (3)	C3—C4—C5	123.3 (3)
N3—C8—C7	113.9 (2)	N1—C2—C3	121.3 (3)
C8—N3—C9	127.1 (2)	N1—C2—C6	116.6 (3)
C8—N3—H3A	116.5	C3—C2—C6	122.1 (3)
C9—N3—H3A	116.5	C4—C5—H5A	109.5
C2—N1—C1	115.5 (2)	C4—C5—H5B	109.5
C1—N2—C4	115.7 (2)	H5A—C5—H5B	109.5
C9—N4—C13	115.7 (2)	C4—C5—H5C	109.5
C8—C7—S1	108.17 (18)	H5A—C5—H5C	109.5
C8—C7—H7A	110.1	H5B—C5—H5C	109.5
S1—C7—H7A	110.1	N4—C13—C12	124.6 (3)
C8—C7—H7B	110.1	N4—C13—H13	117.7
S1—C7—H7B	110.1	C12—C13—H13	117.7
H7A—C7—H7B	108.4	C2—C6—H6A	109.5
N2—C1—N1	127.8 (2)	C2—C6—H6B	109.5
N2—C1—S1	120.1 (2)	H6A—C6—H6B	109.5
N1—C1—S1	112.1 (2)	C2—C6—H6C	109.5
N4—C9—C10	123.3 (2)	H6A—C6—H6C	109.5
N4—C9—N3	113.7 (2)	H6B—C6—H6C	109.5
C10—C9—N3	123.0 (2)	C10—C11—C12	117.8 (2)
C11—C10—C9	119.5 (2)	C10—C11—C14	120.5 (3)
C11—C10—H10	120.3	C12—C11—C14	121.6 (3)
C9—C10—H10	120.3	C11—C14—H14A	109.5
C4—C3—C2	119.0 (3)	C11—C14—H14B	109.5
C4—C3—H3	120.5	H14A—C14—H14B	109.5
C2—C3—H3	120.5	C11—C14—H14C	109.5
C13—C12—C11	119.1 (3)	H14A—C14—H14C	109.5
C13—C12—H12	120.5	H14B—C14—H14C	109.5
C11—C12—H12	120.5

O1—C8—N3—C9	−4.1 (5)	N3—C9—C10—C11	−179.4 (2)
C7—C8—N3—C9	175.6 (2)	C1—N2—C4—C3	−0.5 (4)
O1—C8—C7—S1	0.8 (4)	C1—N2—C4—C5	179.4 (3)
N3—C8—C7—S1	−178.85 (19)	C2—C3—C4—N2	0.2 (4)
C1—S1—C7—C8	−177.95 (19)	C2—C3—C4—C5	−179.7 (3)
C4—N2—C1—N1	0.6 (4)	C1—N1—C2—C3	−0.1 (4)
C4—N2—C1—S1	−179.3 (2)	C1—N1—C2—C6	−179.5 (3)
C2—N1—C1—N2	−0.2 (4)	C4—C3—C2—N1	0.1 (5)
C2—N1—C1—S1	179.6 (2)	C4—C3—C2—C6	179.5 (3)
C7—S1—C1—N2	−1.0 (3)	C9—N4—C13—C12	0.1 (4)
C7—S1—C1—N1	179.1 (2)	C11—C12—C13—N4	−0.1 (5)
C13—N4—C9—C10	−0.5 (4)	C9—C10—C11—C12	−0.9 (4)
C13—N4—C9—N3	179.8 (2)	C9—C10—C11—C14	−179.1 (3)
C8—N3—C9—N4	−177.6 (2)	C13—C12—C11—C10	0.5 (5)
C8—N3—C9—C10	2.8 (4)	C13—C12—C11—C14	178.7 (3)
N4—C9—C10—C11	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4ⁱ	0.86	2.31	3.171 (3)	174
C10—H10···O1	0.93	2.20	2.821 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4ⁱ	0.86	2.31	3.171 (3)	174
C10—H10⋯O1	0.93	2.20	2.821 (4)	123

Symmetry code: (i) .

1 in total

1. 2-(4,6-Dimethyl-pyrimidin-2-ylsulfan-yl)-N-phenyl-acetamide.

Authors: Li-Xin Gao; Guang-Jun Fang; Jin-Guo Feng; Dong Liang; Wei Wang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-03-29

1 in total