Crystal structure of 2,2-dimethyl-N-(5-methyl-pyridin-2-yl)propanamide.

There are two mol-ecules in the asymmetric unit of the title compound, C11H16N2O. The pyridine rings and amide groups overlap almost perfectly (r.m.s. overlay fit = 0.053 Å), but the tertiary butyl groups have different orientations: in one mol-ecule, one of the methyl C atoms is syn to the amide O atom [O-C-C-C = -0.8 (3)°] and in the other the equivalent torsion angle is 31.0 (2)°. In the crystal, the two independent mol-ecules are linked by a pair of N-H⋯N hydrogen bonds in the form of an R 2 (2)(8) loop to form a dimer. A C-H⋯O inter-action connects the dimers into [100] chains.

Related literature

For the synthesis and spectroscopic data, see: Turner (1983 ▸). For related compounds, see: El-Hiti et al. (2015a ▸,b ▸); de Candia et al. (2013 ▸); Smith et al. (2013 ▸, 2012 ▸); Abdel-Megeed et al. (2012 ▸); Joule & Mills (2000 ▸). For the crystal structures of related compounds, see: El-Hiti et al. (2014 ▸); Seidler et al. (2011 ▸); Koch et al. (2008 ▸).

Experimental

Crystal data

C11H16N2O

M = 192.26

Monoclinic,

a = 11.1969 (2) Å

b = 8.6439 (2) Å

c = 23.8844 (5) Å

β = 94.549 (2)°

V = 2304.37 (8) Å3

Z = 8

Cu Kα radiation

μ = 0.57 mm−1

T = 296 K

0.47 × 0.33 × 0.11 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.925, T max = 0.975

8391 measured reflections

4503 independent reflections

3684 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 1.04

4503 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 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, 2015 ▸); 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/S2056989015009378/hb7430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009378/hb7430Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015009378/hb7430Isup3.cml

Click here for additional data file.

11 16 2 . DOI: 10.1107/S2056989015009378/hb7430fig1.tif

The asymmetric unit of C11H16N2O with 50% probability displacement ellipsoids for nonhydrogen atoms.

Click here for additional data file.

. DOI: 10.1107/S2056989015009378/hb7430fig2.tif

The asymmetric unit showing N—H⋯N inter­actions as dotted lines.

CCDC reference: 1401551

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

C11H16N2O	F(000) = 832
Mr = 192.26	Dx = 1.108 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.1969 (2) Å	Cell parameters from 3890 reflections
b = 8.6439 (2) Å	θ = 3.9–73.6°
c = 23.8844 (5) Å	µ = 0.57 mm−1
β = 94.549 (2)°	T = 296 K
V = 2304.37 (8) Å3	Plate, colourless
Z = 8	0.47 × 0.33 × 0.11 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	4503 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	3684 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
ω scans	θmax = 74.0°, θmin = 3.7°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −13→13
Tmin = 0.925, Tmax = 0.975	k = −9→10
8391 measured reflections	l = −29→24

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.081P)2 + 0.208P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.27 e Å−3
4503 reflections	Δρmin = −0.21 e Å−3
262 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0075 (6)

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) 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	Uiso*/Ueq
C1	0.20122 (11)	0.54209 (16)	0.13526 (5)	0.0525 (3)
C2	0.19343 (14)	0.77138 (18)	0.08875 (7)	0.0650 (4)
H2	0.1480	0.8535	0.0736	0.097*
C3	0.31560 (14)	0.77581 (19)	0.08401 (7)	0.0670 (4)
C4	0.38057 (13)	0.6528 (2)	0.10739 (7)	0.0701 (4)
H4	0.4632	0.6499	0.1055	0.105*
C5	0.32450 (12)	0.5351 (2)	0.13327 (7)	0.0654 (4)
H5	0.3681	0.4524	0.1492	0.098*
C6	0.3730 (2)	0.9087 (3)	0.05543 (12)	0.1036 (7)
H6A	0.4566	0.9132	0.0677	0.155*
H6B	0.3349	1.0037	0.0649	0.155*
H6C	0.3639	0.8939	0.0155	0.155*
C7	0.15945 (14)	0.27433 (18)	0.16115 (6)	0.0618 (4)
C8	0.07563 (15)	0.16852 (19)	0.19135 (7)	0.0689 (4)
C9	0.1450 (2)	0.0226 (2)	0.21008 (9)	0.0942 (6)
H9A	0.1777	−0.0243	0.1782	0.141*
H9B	0.0920	−0.0490	0.2263	0.141*
H9C	0.2090	0.0496	0.2375	0.141*
C10	0.0273 (2)	0.2443 (2)	0.24272 (9)	0.0918 (6)
H10A	−0.0163	0.1692	0.2626	0.138*
H10B	−0.0250	0.3280	0.2309	0.138*
H10C	0.0929	0.2832	0.2670	0.138*
C11	−0.0263 (2)	0.1254 (3)	0.14762 (12)	0.1106 (8)
H11A	0.0066	0.0838	0.1149	0.166*
H11B	−0.0726	0.2160	0.1374	0.166*
H11C	−0.0768	0.0494	0.1631	0.166*
C12	−0.12246 (11)	0.71207 (16)	0.19991 (6)	0.0520 (3)
C13	−0.02137 (14)	0.65237 (19)	0.28397 (6)	0.0650 (4)
H13	0.0409	0.5995	0.3037	0.098*
C14	−0.09434 (14)	0.74294 (19)	0.31429 (6)	0.0634 (4)
C15	−0.18413 (15)	0.8222 (2)	0.28376 (7)	0.0710 (4)
H15	−0.2350	0.8861	0.3023	0.106*
C16	−0.19970 (14)	0.8082 (2)	0.22610 (7)	0.0660 (4)
H16	−0.2603	0.8618	0.2054	0.099*
C17	−0.0774 (2)	0.7526 (3)	0.37741 (7)	0.0909 (6)
H17A	−0.0997	0.8538	0.3894	0.136*
H17B	0.0051	0.7335	0.3895	0.136*
H17C	−0.1268	0.6765	0.3936	0.136*
C18	−0.22818 (13)	0.6925 (2)	0.10586 (6)	0.0671 (4)
C19	−0.21118 (14)	0.6626 (2)	0.04398 (6)	0.0714 (4)
C20	−0.1518 (2)	0.5048 (3)	0.03776 (9)	0.1036 (7)
H20A	−0.0736	0.5054	0.0575	0.155*
H20B	−0.1445	0.4838	−0.0013	0.155*
H20C	−0.1999	0.4260	0.0532	0.155*
C21	−0.1325 (2)	0.7892 (3)	0.02172 (9)	0.1074 (8)
H21A	−0.1659	0.8887	0.0293	0.161*
H21B	−0.1291	0.7767	−0.0181	0.161*
H21C	−0.0532	0.7819	0.0400	0.161*
C22	−0.33408 (17)	0.6641 (3)	0.01113 (8)	0.0955 (7)
H22A	−0.3810	0.5790	0.0230	0.143*
H22B	−0.3242	0.6546	−0.0283	0.143*
H22C	−0.3742	0.7596	0.0180	0.143*
N1	0.13561 (10)	0.65829 (14)	0.11338 (5)	0.0578 (3)
N2	0.13689 (10)	0.42840 (14)	0.16285 (5)	0.0577 (3)
H2A	0.0795	0.4589	0.1821	0.086*
N3	−0.03374 (10)	0.63507 (14)	0.22795 (5)	0.0589 (3)
N4	−0.12739 (10)	0.69100 (15)	0.14133 (5)	0.0585 (3)
H4A	−0.0606	0.6758	0.1267	0.088*
O1	0.23876 (14)	0.22212 (15)	0.13479 (7)	0.0942 (4)
O2	−0.32545 (10)	0.7145 (3)	0.12290 (6)	0.1234 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0471 (6)	0.0604 (7)	0.0506 (6)	−0.0005 (5)	0.0069 (5)	−0.0061 (5)
C2	0.0609 (8)	0.0606 (8)	0.0750 (9)	0.0020 (6)	0.0152 (7)	0.0019 (7)
C3	0.0619 (8)	0.0670 (9)	0.0739 (9)	−0.0103 (7)	0.0180 (7)	−0.0082 (7)
C4	0.0458 (7)	0.0872 (11)	0.0783 (10)	−0.0058 (7)	0.0111 (6)	−0.0054 (8)
C5	0.0476 (7)	0.0792 (10)	0.0695 (9)	0.0046 (7)	0.0061 (6)	0.0024 (7)
C6	0.0929 (14)	0.0845 (13)	0.139 (2)	−0.0182 (11)	0.0419 (13)	0.0105 (12)
C7	0.0633 (8)	0.0634 (8)	0.0595 (8)	0.0033 (7)	0.0093 (6)	−0.0058 (6)
C8	0.0743 (10)	0.0600 (8)	0.0730 (9)	−0.0017 (7)	0.0096 (8)	0.0039 (7)
C9	0.1260 (17)	0.0716 (11)	0.0864 (12)	0.0159 (11)	0.0172 (12)	0.0096 (9)
C10	0.1089 (15)	0.0753 (11)	0.0977 (13)	0.0020 (10)	0.0486 (12)	0.0135 (10)
C11	0.0982 (15)	0.1086 (17)	0.1210 (18)	−0.0325 (13)	−0.0168 (14)	0.0207 (14)
C12	0.0441 (6)	0.0584 (7)	0.0541 (7)	−0.0037 (5)	0.0082 (5)	−0.0028 (5)
C13	0.0649 (8)	0.0748 (9)	0.0553 (8)	0.0084 (7)	0.0041 (6)	0.0003 (7)
C14	0.0628 (8)	0.0718 (9)	0.0566 (8)	−0.0045 (7)	0.0101 (6)	−0.0074 (6)
C15	0.0643 (9)	0.0830 (10)	0.0672 (9)	0.0103 (8)	0.0145 (7)	−0.0160 (8)
C16	0.0574 (8)	0.0769 (9)	0.0643 (8)	0.0125 (7)	0.0078 (6)	−0.0056 (7)
C17	0.0947 (13)	0.1195 (16)	0.0590 (9)	0.0039 (12)	0.0092 (9)	−0.0124 (10)
C18	0.0479 (7)	0.0957 (11)	0.0581 (8)	−0.0060 (7)	0.0062 (6)	−0.0059 (7)
C19	0.0574 (8)	0.1030 (12)	0.0540 (8)	−0.0056 (8)	0.0058 (6)	−0.0037 (8)
C20	0.1021 (15)	0.1323 (18)	0.0765 (12)	0.0172 (14)	0.0078 (10)	−0.0312 (12)
C21	0.0894 (13)	0.161 (2)	0.0718 (11)	−0.0318 (14)	0.0046 (10)	0.0262 (13)
C22	0.0681 (10)	0.153 (2)	0.0636 (10)	−0.0080 (12)	−0.0058 (8)	−0.0082 (11)
N1	0.0483 (6)	0.0612 (6)	0.0649 (7)	0.0024 (5)	0.0111 (5)	−0.0014 (5)
N2	0.0517 (6)	0.0616 (7)	0.0612 (6)	0.0020 (5)	0.0141 (5)	0.0003 (5)
N3	0.0564 (6)	0.0654 (7)	0.0555 (6)	0.0082 (5)	0.0078 (5)	−0.0030 (5)
N4	0.0464 (6)	0.0772 (8)	0.0526 (6)	0.0019 (5)	0.0081 (5)	−0.0045 (5)
O1	0.1027 (10)	0.0738 (8)	0.1127 (10)	0.0100 (7)	0.0496 (8)	−0.0114 (7)
O2	0.0451 (6)	0.250 (2)	0.0754 (8)	−0.0005 (9)	0.0067 (5)	−0.0370 (11)

C1—N1	1.3269 (18)	C12—C16	1.384 (2)
C1—C5	1.3862 (19)	C12—N4	1.4077 (17)
C1—N2	1.4122 (17)	C13—N3	1.3427 (19)
C2—N1	1.3346 (19)	C13—C14	1.378 (2)
C2—C3	1.382 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.377 (2)
C3—C4	1.381 (2)	C14—C17	1.507 (2)
C3—C6	1.506 (2)	C15—C16	1.380 (2)
C4—C5	1.368 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—H5	0.9300	C17—H17A	0.9600
C6—H6A	0.9600	C17—H17B	0.9600
C6—H6B	0.9600	C17—H17C	0.9600
C6—H6C	0.9600	C18—O2	1.208 (2)
C7—O1	1.2155 (19)	C18—N4	1.3565 (19)
C7—N2	1.3567 (19)	C18—C19	1.527 (2)
C7—C8	1.531 (2)	C19—C21	1.526 (3)
C8—C10	1.527 (3)	C19—C22	1.529 (2)
C8—C9	1.529 (3)	C19—C20	1.531 (3)
C8—C11	1.531 (3)	C20—H20A	0.9600
C9—H9A	0.9600	C20—H20B	0.9600
C9—H9B	0.9600	C20—H20C	0.9600
C9—H9C	0.9600	C21—H21A	0.9600
C10—H10A	0.9600	C21—H21B	0.9600
C10—H10B	0.9600	C21—H21C	0.9600
C10—H10C	0.9600	C22—H22A	0.9600
C11—H11A	0.9600	C22—H22B	0.9600
C11—H11B	0.9600	C22—H22C	0.9600
C11—H11C	0.9600	N2—H2A	0.8600
C12—N3	1.3314 (18)	N4—H4A	0.8600
N1—C1—C5	122.76 (13)	N3—C13—H13	117.7
N1—C1—N2	115.06 (11)	C14—C13—H13	117.7
C5—C1—N2	122.13 (13)	C15—C14—C13	116.30 (14)
N1—C2—C3	125.05 (15)	C15—C14—C17	122.08 (15)
N1—C2—H2	117.5	C13—C14—C17	121.62 (16)
C3—C2—H2	117.5	C14—C15—C16	120.94 (14)
C4—C3—C2	116.01 (14)	C14—C15—H15	119.5
C4—C3—C6	122.73 (16)	C16—C15—H15	119.5
C2—C3—C6	121.25 (17)	C15—C16—C12	118.01 (14)
C5—C4—C3	120.60 (14)	C15—C16—H16	121.0
C5—C4—H4	119.7	C12—C16—H16	121.0
C3—C4—H4	119.7	C14—C17—H17A	109.5
C4—C5—C1	118.49 (15)	C14—C17—H17B	109.5
C4—C5—H5	120.8	H17A—C17—H17B	109.5
C1—C5—H5	120.8	C14—C17—H17C	109.5
C3—C6—H6A	109.5	H17A—C17—H17C	109.5
C3—C6—H6B	109.5	H17B—C17—H17C	109.5
H6A—C6—H6B	109.5	O2—C18—N4	121.25 (14)
C3—C6—H6C	109.5	O2—C18—C19	122.54 (14)
H6A—C6—H6C	109.5	N4—C18—C19	116.20 (13)
H6B—C6—H6C	109.5	C21—C19—C18	109.61 (16)
O1—C7—N2	121.70 (15)	C21—C19—C22	109.63 (17)
O1—C7—C8	121.50 (15)	C18—C19—C22	108.60 (14)
N2—C7—C8	116.72 (13)	C21—C19—C20	109.78 (18)
C10—C8—C9	108.82 (16)	C18—C19—C20	109.45 (16)
C10—C8—C11	111.11 (19)	C22—C19—C20	109.75 (18)
C9—C8—C11	109.45 (17)	C19—C20—H20A	109.5
C10—C8—C7	113.06 (14)	C19—C20—H20B	109.5
C9—C8—C7	108.31 (15)	H20A—C20—H20B	109.5
C11—C8—C7	106.00 (15)	C19—C20—H20C	109.5
C8—C9—H9A	109.5	H20A—C20—H20C	109.5
C8—C9—H9B	109.5	H20B—C20—H20C	109.5
H9A—C9—H9B	109.5	C19—C21—H21A	109.5
C8—C9—H9C	109.5	C19—C21—H21B	109.5
H9A—C9—H9C	109.5	H21A—C21—H21B	109.5
H9B—C9—H9C	109.5	C19—C21—H21C	109.5
C8—C10—H10A	109.5	H21A—C21—H21C	109.5
C8—C10—H10B	109.5	H21B—C21—H21C	109.5
H10A—C10—H10B	109.5	C19—C22—H22A	109.5
C8—C10—H10C	109.5	C19—C22—H22B	109.5
H10A—C10—H10C	109.5	H22A—C22—H22B	109.5
H10B—C10—H10C	109.5	C19—C22—H22C	109.5
C8—C11—H11A	109.5	H22A—C22—H22C	109.5
C8—C11—H11B	109.5	H22B—C22—H22C	109.5
H11A—C11—H11B	109.5	C1—N1—C2	117.08 (12)
C8—C11—H11C	109.5	C7—N2—C1	124.47 (12)
H11A—C11—H11C	109.5	C7—N2—H2A	117.8
H11B—C11—H11C	109.5	C1—N2—H2A	117.8
N3—C12—C16	122.75 (13)	C12—N3—C13	117.35 (12)
N3—C12—N4	113.83 (11)	C18—N4—C12	125.79 (12)
C16—C12—N4	123.38 (13)	C18—N4—H4A	117.1
N3—C13—C14	124.64 (14)	C12—N4—H4A	117.1
N1—C2—C3—C4	−0.6 (3)	O2—C18—C19—C21	119.0 (2)
N1—C2—C3—C6	−179.97 (18)	N4—C18—C19—C21	−61.9 (2)
C2—C3—C4—C5	0.2 (2)	O2—C18—C19—C22	−0.8 (3)
C6—C3—C4—C5	179.56 (18)	N4—C18—C19—C22	178.35 (18)
C3—C4—C5—C1	0.3 (2)	O2—C18—C19—C20	−120.6 (2)
N1—C1—C5—C4	−0.3 (2)	N4—C18—C19—C20	58.5 (2)
N2—C1—C5—C4	−177.72 (14)	C5—C1—N1—C2	0.0 (2)
O1—C7—C8—C10	151.67 (19)	N2—C1—N1—C2	177.54 (12)
N2—C7—C8—C10	−31.6 (2)	C3—C2—N1—C1	0.5 (2)
O1—C7—C8—C9	31.0 (2)	O1—C7—N2—C1	−0.2 (2)
N2—C7—C8—C9	−152.30 (15)	C8—C7—N2—C1	−176.94 (13)
O1—C7—C8—C11	−86.4 (2)	N1—C1—N2—C7	142.20 (14)
N2—C7—C8—C11	90.33 (19)	C5—C1—N2—C7	−40.2 (2)
N3—C13—C14—C15	−1.3 (3)	C16—C12—N3—C13	0.6 (2)
N3—C13—C14—C17	177.95 (17)	N4—C12—N3—C13	178.41 (13)
C13—C14—C15—C16	0.9 (3)	C14—C13—N3—C12	0.5 (2)
C17—C14—C15—C16	−178.27 (18)	O2—C18—N4—C12	0.7 (3)
C14—C15—C16—C12	0.1 (3)	C19—C18—N4—C12	−178.44 (15)
N3—C12—C16—C15	−0.9 (2)	N3—C12—N4—C18	148.58 (15)
N4—C12—C16—C15	−178.46 (15)	C16—C12—N4—C18	−33.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3	0.86	2.31	3.1192 (16)	156
N4—H4A···N1	0.86	2.25	3.0837 (16)	163
C4—H4···O2i	0.93	2.43	3.3262 (19)	160

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2AN3	0.86	2.31	3.1192(16)	156
N4H4AN1	0.86	2.25	3.0837(16)	163
C4H4O2i	0.93	2.43	3.3262(19)	160

Symmetry code: (i) .