Literature DB >> 24765040

2,2-Dimethyl-N-(4-methyl-pyridin-2-yl)propanamide.

Gamal A El-Hiti¹, Keith Smith², Asim A Balakit³, Amany S Hegazy², Benson M Kariuki².

Abstract

In the title compound, C11H16N2O, the dihedral angle between the mean plane of the 4-methypyridine group and the plane of the amide link is 16.7 (1)°, and there is a short intra-molecular C-H⋯O contact. Hydrogen bonding (N-H⋯O) between amide groups forms chains parallel to the b axis. Pairs of methyl-pyridine groups from mol-ecules in adjacent chains are parallel but there is minimal π-π inter-action.

Entities: Chemical Disease Gene

Year: 2014 PMID： 24765040 PMCID： PMC3998503 DOI： 10.1107/S1600536814003729

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

Related literature

For biological applications of related compounds, see: de Candia et al. (2013 ▶); Thorat et al. (2013 ▶); Abdel-Megeed et al. (2012 ▶). For convenient routes for modifying pyridine derivatives, see: Smith et al. (2013 ▶); Smith et al. (2012 ▶); El-Hiti (2003 ▶); Joule & Mills (2000 ▶); Smith et al. (1994 ▶, 1995 ▶, 1999 ▶); Turner (1983 ▶). For the X-ray structures of related compounds, see: Mazik & Sicking (2004 ▶); Mazik et al. (2004 ▶); Hodorowicz et al. (2007 ▶); Koch et al. (2008 ▶); Liang et al. (2008 ▶); Seidler et al. (2011 ▶).

Experimental

Crystal data

C11H16N2O M = 192.26 Orthorhombic, a = 10.7954 (3) Å b = 10.1809 (2) Å c = 20.8390 (5) Å V = 2290.35 (10) Å3 Z = 8 Cu Kα radiation μ = 0.58 mm−1 T = 296 K 0.27 × 0.19 × 0.14 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.930, T max = 0.957 5219 measured reflections 2253 independent reflections 1808 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.154 S = 1.08 2253 reflections 132 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.14 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 ▶) and CHEMDRAW Ultra (CambridgeSoft, 2001 ▶). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814003729/mw2120sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003729/mw2120Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814003729/mw2120Isup3.cml CCDC reference: Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₁H₁₆N₂O	D_x = 1.115 Mg m⁻³
M_r = 192.26	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 1808 reflections
a = 10.7954 (3) Å	θ = 4.2–74.0°
b = 10.1809 (2) Å	µ = 0.58 mm⁻¹
c = 20.8390 (5) Å	T = 296 K
V = 2290.35 (10) Å³	Block, colourless
Z = 8	0.27 × 0.19 × 0.14 mm
F(000) = 832

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1808 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	R_int = 0.017
ω scans	θ_max = 74.0°, θ_min = 4.2°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −7→13
T_min = 0.930, T_max = 0.957	k = −12→8
5219 measured reflections	l = −25→20
2253 independent reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0734P)² + 0.4299P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.154	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.16 e Å⁻³
2253 reflections	Δρ_min = −0.14 e Å⁻³
132 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0037 (5)

Experimental. Absorption correction: CrysAlisPro (Agilent, 2014): Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	U_iso*/U_eq
C1	0.90730 (14)	0.81479 (14)	0.59591 (7)	0.0489 (4)
C2	1.0228 (2)	0.6963 (2)	0.52600 (11)	0.0816 (6)
H2	1.0345	0.6201	0.5021	0.098*
C3	1.1102 (2)	0.7922 (2)	0.52141 (11)	0.0792 (6)
H3	1.1786	0.7811	0.4948	0.095*
C4	1.09637 (16)	0.90571 (19)	0.55651 (9)	0.0632 (5)
C5	0.99149 (14)	0.91744 (16)	0.59451 (8)	0.0552 (4)
H5	0.9779	0.9929	0.6186	0.066*
C6	1.1912 (2)	1.0138 (3)	0.55444 (12)	0.0922 (7)
H6A	1.2409	1.0107	0.5926	0.138*
H6B	1.1499	1.0972	0.5520	0.138*
H6C	1.2431	1.0025	0.5175	0.138*
C7	0.74226 (15)	0.91931 (14)	0.66136 (8)	0.0515 (4)
C8	0.62472 (16)	0.88824 (16)	0.69967 (9)	0.0606 (5)
C9	0.6598 (2)	0.8017 (2)	0.75696 (11)	0.0851 (7)
H9A	0.7235	0.8442	0.7815	0.128*
H9B	0.6895	0.7185	0.7418	0.128*
H9C	0.5882	0.7883	0.7835	0.128*
C10	0.5677 (2)	1.0158 (2)	0.72312 (13)	0.0997 (9)
H10A	0.6251	1.0600	0.7509	0.149*
H10B	0.4929	0.9970	0.7463	0.149*
H10C	0.5490	1.0709	0.6870	0.149*
C11	0.53133 (19)	0.8146 (3)	0.65810 (13)	0.0933 (8)
H11A	0.4578	0.7976	0.6826	0.140*
H11B	0.5668	0.7329	0.6442	0.140*
H11C	0.5107	0.8670	0.6213	0.140*
N1	0.92138 (14)	0.70437 (14)	0.56251 (8)	0.0654 (4)
N2	0.79937 (12)	0.81473 (12)	0.63366 (7)	0.0554 (4)
H2A	0.7654	0.7394	0.6400	0.067*
O1	0.78283 (12)	1.03049 (11)	0.65664 (7)	0.0699 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0475 (8)	0.0469 (8)	0.0523 (8)	0.0056 (6)	0.0003 (6)	0.0012 (6)
C2	0.0788 (13)	0.0735 (12)	0.0924 (14)	0.0131 (10)	0.0224 (11)	−0.0152 (11)
C3	0.0626 (11)	0.0889 (14)	0.0861 (13)	0.0180 (10)	0.0226 (10)	0.0029 (11)
C4	0.0481 (9)	0.0720 (11)	0.0694 (10)	0.0027 (8)	0.0020 (7)	0.0171 (9)
C5	0.0518 (9)	0.0531 (9)	0.0607 (9)	0.0001 (7)	0.0028 (7)	0.0032 (7)
C6	0.0587 (11)	0.1052 (17)	0.1126 (18)	−0.0166 (11)	0.0083 (11)	0.0244 (15)
C7	0.0533 (8)	0.0390 (7)	0.0622 (8)	0.0022 (6)	0.0061 (7)	−0.0009 (6)
C8	0.0592 (10)	0.0478 (8)	0.0749 (10)	0.0016 (7)	0.0190 (8)	−0.0021 (7)
C9	0.0969 (16)	0.0788 (13)	0.0798 (13)	0.0035 (12)	0.0275 (12)	0.0104 (10)
C10	0.1026 (17)	0.0605 (12)	0.136 (2)	0.0135 (11)	0.0640 (16)	−0.0025 (12)
C11	0.0548 (11)	0.1121 (19)	0.1129 (18)	−0.0056 (11)	0.0126 (12)	−0.0159 (15)
N1	0.0646 (9)	0.0546 (8)	0.0770 (9)	0.0056 (7)	0.0107 (7)	−0.0124 (7)
N2	0.0551 (8)	0.0401 (7)	0.0711 (8)	−0.0038 (5)	0.0153 (6)	−0.0040 (6)
O1	0.0673 (8)	0.0389 (6)	0.1034 (10)	−0.0010 (5)	0.0213 (7)	−0.0030 (6)

C1—N1	1.3310 (19)	C7—N2	1.3590 (19)
C1—C5	1.385 (2)	C7—C8	1.532 (2)
C1—N2	1.406 (2)	C8—C10	1.518 (2)
C2—N1	1.336 (3)	C8—C11	1.526 (3)
C2—C3	1.361 (3)	C8—C9	1.531 (3)
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.376 (3)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.387 (2)	C10—H10A	0.9600
C4—C6	1.503 (3)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—H6A	0.9600	C11—H11A	0.9600
C6—H6B	0.9600	C11—H11B	0.9600
C6—H6C	0.9600	C11—H11C	0.9600
C7—O1	1.2177 (18)	N2—H2A	0.8600

N1—C1—C5	123.45 (15)	C11—C8—C9	108.85 (18)
N1—C1—N2	112.76 (13)	C10—C8—C7	109.09 (14)
C5—C1—N2	123.78 (14)	C11—C8—C7	110.66 (15)
N1—C2—C3	124.35 (19)	C9—C8—C7	108.69 (15)
N1—C2—H2	117.8	C8—C9—H9A	109.5
C3—C2—H2	117.8	C8—C9—H9B	109.5
C2—C3—C4	119.33 (18)	H9A—C9—H9B	109.5
C2—C3—H3	120.3	C8—C9—H9C	109.5
C4—C3—H3	120.3	H9A—C9—H9C	109.5
C3—C4—C5	117.68 (17)	H9B—C9—H9C	109.5
C3—C4—C6	121.72 (19)	C8—C10—H10A	109.5
C5—C4—C6	120.60 (19)	C8—C10—H10B	109.5
C1—C5—C4	118.87 (16)	H10A—C10—H10B	109.5
C1—C5—H5	120.6	C8—C10—H10C	109.5
C4—C5—H5	120.6	H10A—C10—H10C	109.5
C4—C6—H6A	109.5	H10B—C10—H10C	109.5
C4—C6—H6B	109.5	C8—C11—H11A	109.5
H6A—C6—H6B	109.5	C8—C11—H11B	109.5
C4—C6—H6C	109.5	H11A—C11—H11B	109.5
H6A—C6—H6C	109.5	C8—C11—H11C	109.5
H6B—C6—H6C	109.5	H11A—C11—H11C	109.5
O1—C7—N2	122.06 (15)	H11B—C11—H11C	109.5
O1—C7—C8	122.14 (14)	C1—N1—C2	116.32 (16)
N2—C7—C8	115.80 (13)	C7—N2—C1	127.83 (13)
C10—C8—C11	109.58 (19)	C7—N2—H2A	116.1
C10—C8—C9	109.95 (18)	C1—N2—H2A	116.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.22	3.0644 (17)	168
C5—H5···O1	0.93	2.28	2.842 (2)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.22	3.0644 (17)	168
C5—H5⋯O1	0.93	2.28	2.842 (2)	118

Symmetry code: (i) .

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