Literature DB >> 26029437

Crystal structure of 2,2-dimethyl-N-(pyridin-3-yl)propanamide.

Gamal A El-Hiti¹, Keith Smith², Amany S Hegazy², Saud A Alanazi¹, Benson M Kariuki².

Abstract

In the title compound, C10H14N2O, the pyridine ring is inclined to the mean plane of the amide moiety [N-C(=O)C] by 17.60 (8)°. There is an intra-molecular C-H⋯O hydrogen bond present involving the carbonyl O atom. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains propagating along [100]. The tert-butyl group is disordered over two sets of sites with a refined occupancy ratio of 0.758 (12):0.242 (12).

Entities: Chemical Disease Species

Keywords: N—H⋯N hydrogen bonds; crystal structure; propanamide; pyridine

Year: 2015 PMID： 26029437 PMCID： PMC4438820 DOI： 10.1107/S2056989015005289

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For related biologically active pyridine derivatives, see: de Candia et al. (2013 ▸); Thorat et al. (2013 ▸); Abdel-Megeed et al. (2012 ▸). For pyridine ring-system modifications, see: El-Hiti et al. (2015 ▸); Smith et al. (2012 ▸, 2013 ▸); Londregan et al. (2009 ▸); Joule & Mills (2000 ▸); Turner (1983 ▸). For the crystal structures of related compounds, see: El-Hiti et al. (2014 ▸); Seidler et al. (2011 ▸); Koch et al. (2008 ▸); Mazik et al. (2004 ▸).

Experimental

Crystal data

C10H14N2O M = 178.23 Orthorhombic, a = 11.2453 (3) Å b = 10.5272 (3) Å c = 17.5339 (6) Å V = 2075.69 (11) Å3 Z = 8 Cu Kα radiation μ = 0.60 mm−1 T = 293 K 0.23 × 0.19 × 0.06 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.840, T max = 1.000 7164 measured reflections 2065 independent reflections 1722 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.127 S = 1.05 2065 reflections 153 parameters 114 restraints H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.16 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, 2015 ▸); 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/S2056989015005289/su5094sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005289/su5094Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015005289/su5094Isup3.cml Click here for additional data file. t . DOI: 10.1107/S2056989015005289/su5094fig1.tif The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered t-butyl group is shown. Click here for additional data file. b t . DOI: 10.1107/S2056989015005289/su5094fig2.tif Crystal packing of the title compound, viewed along the b axis, with the N—H⋯N interactions shown as dashed lines (see Table 1 for details). The minor component of the disordered t-butyl group has been omitted for clarity. CCDC reference: 1054113 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₀H₁₄N₂O	D_x = 1.141 Mg m⁻³
M_r = 178.23	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 3061 reflections
a = 11.2453 (3) Å	θ = 5.0–73.4°
b = 10.5272 (3) Å	µ = 0.60 mm⁻¹
c = 17.5339 (6) Å	T = 293 K
V = 2075.69 (11) Å³	Plate, colourless
Z = 8	0.23 × 0.19 × 0.06 mm
F(000) = 768

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	2065 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	1722 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.017
ω scans	θ_max = 73.8°, θ_min = 5.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −14→8
T_min = 0.840, T_max = 1.000	k = −13→12
7164 measured reflections	l = −20→21

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0688P)² + 0.2387P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.127	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.19 e Å⁻³
2065 reflections	Δρ_min = −0.16 e Å⁻³
153 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
114 restraints	Extinction coefficient: 0.0016 (4)

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	Occ. (<1)
C1	0.72804 (10)	0.10403 (12)	0.27358 (7)	0.0490 (3)
C2	0.61380 (11)	0.14128 (14)	0.25328 (8)	0.0585 (4)
H2	0.5822	0.2140	0.2756	0.070*
C3	0.59204 (13)	−0.02662 (15)	0.17123 (8)	0.0663 (4)
H3	0.5452	−0.0722	0.1371	0.080*
C4	0.70473 (13)	−0.06915 (16)	0.18680 (9)	0.0702 (4)
H4	0.7344	−0.1414	0.1630	0.084*
C5	0.77323 (12)	−0.00301 (14)	0.23832 (8)	0.0619 (4)
H5	0.8499	−0.0303	0.2494	0.074*
C6	0.76123 (12)	0.24951 (14)	0.38234 (8)	0.0585 (3)
C7	0.85629 (13)	0.29549 (15)	0.43884 (9)	0.0671 (4)
C8	0.9594 (3)	0.3605 (4)	0.3935 (2)	0.0798 (10)	0.758 (12)
H8A	0.9277	0.4278	0.3627	0.120*	0.758 (12)
H8B	0.9974	0.2988	0.3613	0.120*	0.758 (12)
H8C	1.0165	0.3947	0.4287	0.120*	0.758 (12)
C9	0.9077 (5)	0.1835 (4)	0.4813 (4)	0.0838 (11)	0.758 (12)
H9A	0.9680	0.2125	0.5159	0.126*	0.758 (12)
H9B	0.9421	0.1250	0.4455	0.126*	0.758 (12)
H9C	0.8458	0.1417	0.5094	0.126*	0.758 (12)
C10	0.8023 (4)	0.3941 (7)	0.4916 (4)	0.1205 (18)	0.758 (12)
H10A	0.7365	0.3574	0.5186	0.181*	0.758 (12)
H10B	0.7751	0.4653	0.4621	0.181*	0.758 (12)
H10C	0.8613	0.4222	0.5274	0.181*	0.758 (12)
C8A	0.9208 (16)	0.4067 (14)	0.4095 (8)	0.108 (4)	0.242 (12)
H8D	0.9534	0.3873	0.3602	0.162*	0.242 (12)
H8E	0.9841	0.4281	0.4439	0.162*	0.242 (12)
H8F	0.8672	0.4772	0.4052	0.162*	0.242 (12)
C9A	0.9385 (16)	0.1880 (15)	0.4658 (11)	0.089 (4)	0.242 (12)
H9D	0.8920	0.1137	0.4766	0.133*	0.242 (12)
H9E	0.9796	0.2142	0.5111	0.133*	0.242 (12)
H9F	0.9953	0.1690	0.4265	0.133*	0.242 (12)
C10A	0.7832 (11)	0.3342 (17)	0.5131 (6)	0.098 (4)	0.242 (12)
H10D	0.7211	0.3924	0.4993	0.147*	0.242 (12)
H10E	0.8355	0.3739	0.5491	0.147*	0.242 (12)
H10F	0.7488	0.2595	0.5355	0.147*	0.242 (12)
N1	0.79882 (8)	0.16796 (11)	0.32735 (6)	0.0543 (3)
H1	0.8741	0.1539	0.3252	0.065*
N2	0.54740 (9)	0.07752 (13)	0.20320 (7)	0.0650 (3)
O1	0.65818 (9)	0.28385 (14)	0.38687 (7)	0.0885 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (6)	0.0624 (7)	0.0478 (6)	0.0007 (5)	0.0006 (5)	0.0031 (5)
C2	0.0400 (6)	0.0715 (8)	0.0640 (7)	0.0064 (6)	−0.0046 (5)	−0.0063 (6)
C3	0.0529 (7)	0.0841 (9)	0.0617 (8)	−0.0037 (7)	−0.0065 (6)	−0.0111 (7)
C4	0.0630 (9)	0.0778 (9)	0.0697 (9)	0.0116 (7)	−0.0067 (7)	−0.0172 (7)
C5	0.0450 (7)	0.0766 (8)	0.0641 (8)	0.0130 (6)	−0.0051 (6)	−0.0078 (6)
C6	0.0461 (7)	0.0715 (8)	0.0579 (7)	0.0057 (6)	−0.0020 (6)	−0.0039 (6)
C7	0.0620 (8)	0.0739 (8)	0.0653 (8)	−0.0024 (7)	−0.0092 (6)	−0.0103 (7)
C8	0.0716 (17)	0.0753 (17)	0.0926 (19)	−0.0182 (13)	−0.0135 (13)	0.0017 (14)
C9	0.089 (3)	0.101 (2)	0.062 (2)	−0.0202 (16)	−0.0235 (18)	0.0146 (16)
C10	0.098 (2)	0.134 (4)	0.129 (4)	−0.002 (3)	−0.004 (2)	−0.073 (3)
C8A	0.129 (8)	0.107 (7)	0.087 (6)	−0.026 (6)	−0.027 (6)	0.000 (6)
C9A	0.080 (7)	0.116 (7)	0.071 (7)	0.008 (6)	−0.023 (5)	−0.011 (5)
C10A	0.102 (6)	0.115 (8)	0.076 (5)	0.013 (6)	−0.026 (4)	−0.046 (5)
N1	0.0341 (5)	0.0708 (7)	0.0581 (6)	0.0041 (4)	−0.0035 (4)	−0.0056 (5)
N2	0.0408 (6)	0.0867 (8)	0.0676 (7)	0.0032 (5)	−0.0078 (5)	−0.0079 (6)
O1	0.0543 (6)	0.1273 (10)	0.0838 (8)	0.0235 (6)	−0.0048 (5)	−0.0356 (7)

C1—C5	1.3820 (19)	C8—H8A	0.9600
C1—C2	1.3895 (17)	C8—H8B	0.9600
C1—N1	1.4054 (16)	C8—H8C	0.9600
C2—N2	1.3339 (18)	C9—H9A	0.9600
C2—H2	0.9300	C9—H9B	0.9600
C3—N2	1.3297 (19)	C9—H9C	0.9600
C3—C4	1.372 (2)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.376 (2)	C10—H10C	0.9600
C4—H4	0.9300	C8A—H8D	0.9600
C5—H5	0.9300	C8A—H8E	0.9600
C6—O1	1.2165 (17)	C8A—H8F	0.9600
C6—N1	1.3585 (17)	C9A—H9D	0.9600
C6—C7	1.5356 (19)	C9A—H9E	0.9600
C7—C8A	1.470 (7)	C9A—H9F	0.9600
C7—C9	1.510 (4)	C10A—H10D	0.9600
C7—C10	1.517 (4)	C10A—H10E	0.9600
C7—C9A	1.536 (8)	C10A—H10F	0.9600
C7—C8	1.563 (3)	N1—H1	0.8600
C7—C10A	1.593 (7)

C5—C1—C2	117.09 (12)	H8B—C8—H8C	109.5
C5—C1—N1	118.83 (10)	C7—C9—H9A	109.5
C2—C1—N1	124.07 (11)	C7—C9—H9B	109.5
N2—C2—C1	122.97 (12)	H9A—C9—H9B	109.5
N2—C2—H2	118.5	C7—C9—H9C	109.5
C1—C2—H2	118.5	H9A—C9—H9C	109.5
N2—C3—C4	122.28 (13)	H9B—C9—H9C	109.5
N2—C3—H3	118.9	C7—C10—H10A	109.5
C4—C3—H3	118.9	C7—C10—H10B	109.5
C3—C4—C5	118.86 (14)	H10A—C10—H10B	109.5
C3—C4—H4	120.6	C7—C10—H10C	109.5
C5—C4—H4	120.6	H10A—C10—H10C	109.5
C4—C5—C1	120.02 (12)	H10B—C10—H10C	109.5
C4—C5—H5	120.0	C7—C8A—H8D	109.5
C1—C5—H5	120.0	C7—C8A—H8E	109.5
O1—C6—N1	122.04 (13)	H8D—C8A—H8E	109.5
O1—C6—C7	121.83 (13)	C7—C8A—H8F	109.5
N1—C6—C7	116.13 (11)	H8D—C8A—H8F	109.5
C9—C7—C10	112.8 (3)	H8E—C8A—H8F	109.5
C8A—C7—C6	111.6 (5)	C7—C9A—H9D	109.5
C9—C7—C6	109.8 (3)	C7—C9A—H9E	109.5
C10—C7—C6	109.3 (2)	H9D—C9A—H9E	109.5
C8A—C7—C9A	113.4 (7)	C7—C9A—H9F	109.5
C6—C7—C9A	112.7 (9)	H9D—C9A—H9F	109.5
C9—C7—C8	107.9 (2)	H9E—C9A—H9F	109.5
C10—C7—C8	107.9 (2)	C7—C10A—H10D	109.5
C6—C7—C8	109.05 (17)	C7—C10A—H10E	109.5
C8A—C7—C10A	109.7 (5)	H10D—C10A—H10E	109.5
C6—C7—C10A	104.4 (5)	C7—C10A—H10F	109.5
C9A—C7—C10A	104.3 (6)	H10D—C10A—H10F	109.5
C7—C8—H8A	109.5	H10E—C10A—H10F	109.5
C7—C8—H8B	109.5	C6—N1—C1	127.05 (10)
H8A—C8—H8B	109.5	C6—N1—H1	116.5
C7—C8—H8C	109.5	C1—N1—H1	116.5
H8A—C8—H8C	109.5	C3—N2—C2	118.76 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.25	2.8263 (18)	119
N1—H1···N2ⁱ	0.86	2.17	3.0012 (15)	164

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2O1	0.93	2.25	2.8263(18)	119
N1H1N2ⁱ	0.86	2.17	3.0012(15)	164

Symmetry code: (i) .

9 in total

1. Molecular recognition of carbohydrates with acyclic pyridine-based receptors.

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3. Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates.

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