2,6-Dimethyl-N-(2-methyl-phen-yl)-1,3-dioxan-4-amine.

In the title compound, C13H19NO2, the dioxane ring adopts a chair conformation and its mean plane makes a dihedral angle of 45.36 (8)° with the phenyl ring. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with R (2) 2(12) ring motifs. These dimers are consolidated by pairs of C-H⋯O hydrogen bonds with R (2) 2(8) ring motifs.

Related literature

For applications of 1,3-dioxane derivatives, see: Wang et al. (1996a ▶,b ▶); Yuan et al. (2005 ▶). Dioxane rings are frequently encountered in many bioactive mol­ecules, some of which are cytotoxic agents (Aubele et al., 2005 ▶) and anti­muscarinic agents (Marucci et al., 2005 ▶). For related crystal structures, see: Chuprunov et al. (1981 ▶); Thevenet et al. (2010 ▶); Fatima et al. (2013 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H19NO2

M = 221.29

Monoclinic,

a = 8.0209 (2) Å

b = 7.8762 (2) Å

c = 20.4293 (5) Å

β = 99.066 (2)°

V = 1274.48 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.692, T max = 0.746

12359 measured reflections

3177 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.03

3177 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025294/su2643sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025294/su2643Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025294/su2643Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H19NO2	F(000) = 480
Mr = 221.29	Dx = 1.153 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3177 reflections
a = 8.0209 (2) Å	θ = 2.0–28.4°
b = 7.8762 (2) Å	µ = 0.08 mm−1
c = 20.4293 (5) Å	T = 293 K
β = 99.066 (2)°	Block, colourless
V = 1274.48 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3177 independent reflections
Radiation source: fine-focus sealed tube	2481 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω and φ scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.692, Tmax = 0.746	k = −10→10
12359 measured reflections	l = −26→27

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1687P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3177 reflections	Δρmax = 0.18 e Å−3
152 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (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.

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	Uiso*/Ueq
H1	0.3087 (18)	0.4830 (19)	0.5783 (7)	0.067 (4)*
C1	0.31391 (18)	0.68745 (18)	0.35171 (7)	0.0682 (4)
H1A	0.3217	0.6610	0.3064	0.102*
H1B	0.4212	0.7278	0.3737	0.102*
H1C	0.2300	0.7738	0.3531	0.102*
C2	0.26506 (14)	0.53043 (15)	0.38614 (6)	0.0509 (3)
H2	0.1570	0.4884	0.3627	0.061*
C3	0.24940 (13)	0.56014 (14)	0.45810 (5)	0.0474 (3)
H3A	0.3511	0.6147	0.4804	0.057*
H3B	0.1550	0.6354	0.4607	0.057*
C4	0.22287 (12)	0.39494 (14)	0.49256 (5)	0.0457 (3)
H4	0.1121	0.3489	0.4739	0.055*
C5	0.35637 (15)	0.25112 (14)	0.41290 (6)	0.0511 (3)
H5	0.2477	0.2066	0.3910	0.061*
C6	0.4939 (2)	0.12583 (18)	0.40646 (8)	0.0727 (4)
H6A	0.4992	0.1072	0.3604	0.109*
H6B	0.4703	0.0204	0.4267	0.109*
H6C	0.6000	0.1697	0.4281	0.109*
C7	0.19069 (13)	0.28783 (15)	0.60341 (5)	0.0475 (3)
C8	0.13383 (15)	0.12993 (17)	0.57909 (7)	0.0570 (3)
H8	0.1240	0.1079	0.5339	0.068*
C9	0.09169 (17)	0.00538 (19)	0.62110 (8)	0.0684 (4)
H9	0.0524	−0.0991	0.6040	0.082*
C10	0.10746 (19)	0.0348 (2)	0.68794 (8)	0.0773 (4)
H10	0.0799	−0.0494	0.7163	0.093*
C11	0.16463 (19)	0.1905 (2)	0.71237 (7)	0.0739 (4)
H11	0.1760	0.2096	0.7578	0.089*
C12	0.20590 (14)	0.31981 (18)	0.67183 (6)	0.0573 (3)
C13	0.2628 (2)	0.4902 (2)	0.69976 (7)	0.0778 (4)
H13A	0.2537	0.4935	0.7460	0.117*
H13B	0.1929	0.5772	0.6768	0.117*
H13C	0.3781	0.5088	0.6943	0.117*
N1	0.22865 (13)	0.41904 (13)	0.56182 (5)	0.0508 (2)
O1	0.35151 (9)	0.27540 (10)	0.48107 (4)	0.0477 (2)
O2	0.39299 (10)	0.40450 (10)	0.38245 (4)	0.0509 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0724 (8)	0.0649 (8)	0.0671 (8)	0.0025 (7)	0.0106 (6)	0.0160 (6)
C2	0.0435 (5)	0.0577 (7)	0.0495 (6)	−0.0018 (5)	0.0009 (4)	0.0032 (5)
C3	0.0407 (5)	0.0495 (6)	0.0513 (6)	0.0054 (4)	0.0047 (4)	−0.0003 (5)
C4	0.0375 (5)	0.0529 (6)	0.0461 (6)	−0.0011 (4)	0.0045 (4)	−0.0026 (4)
C5	0.0567 (6)	0.0469 (6)	0.0500 (6)	−0.0108 (5)	0.0095 (5)	−0.0089 (5)
C6	0.0930 (10)	0.0516 (7)	0.0778 (9)	0.0049 (7)	0.0270 (8)	−0.0136 (6)
C7	0.0377 (5)	0.0567 (7)	0.0486 (6)	0.0031 (4)	0.0085 (4)	0.0021 (5)
C8	0.0502 (6)	0.0623 (7)	0.0587 (7)	−0.0030 (5)	0.0096 (5)	0.0005 (6)
C9	0.0576 (7)	0.0630 (8)	0.0861 (10)	−0.0058 (6)	0.0158 (6)	0.0088 (7)
C10	0.0706 (9)	0.0835 (11)	0.0808 (10)	−0.0003 (8)	0.0211 (7)	0.0279 (8)
C11	0.0714 (8)	0.0987 (12)	0.0537 (7)	0.0022 (8)	0.0161 (6)	0.0137 (7)
C12	0.0497 (6)	0.0738 (8)	0.0497 (6)	0.0029 (6)	0.0122 (5)	−0.0002 (6)
C13	0.0895 (10)	0.0930 (11)	0.0544 (8)	−0.0102 (9)	0.0217 (7)	−0.0172 (7)
N1	0.0514 (5)	0.0556 (6)	0.0455 (5)	−0.0050 (4)	0.0079 (4)	−0.0035 (4)
O1	0.0496 (4)	0.0458 (4)	0.0475 (4)	0.0004 (3)	0.0073 (3)	−0.0025 (3)
O2	0.0523 (4)	0.0504 (5)	0.0517 (4)	−0.0042 (3)	0.0136 (3)	−0.0022 (3)

C1—C2	1.5048 (17)	C6—H6B	0.9600
C1—H1A	0.9600	C6—H6C	0.9600
C1—H1B	0.9600	C7—C8	1.3893 (17)
C1—H1C	0.9600	C7—N1	1.4014 (15)
C2—O2	1.4376 (14)	C7—C12	1.4065 (16)
C2—C3	1.5133 (16)	C8—C9	1.3800 (18)
C2—H2	0.9800	C8—H8	0.9300
C3—C4	1.5103 (16)	C9—C10	1.371 (2)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	C10—C11	1.375 (2)
C4—N1	1.4212 (14)	C10—H10	0.9300
C4—O1	1.4431 (13)	C11—C12	1.386 (2)
C4—H4	0.9800	C11—H11	0.9300
C5—O2	1.4108 (14)	C12—C13	1.501 (2)
C5—O1	1.4122 (13)	C13—H13A	0.9600
C5—C6	1.5010 (18)	C13—H13B	0.9600
C5—H5	0.9800	C13—H13C	0.9600
C6—H6A	0.9600	N1—H1	0.843 (15)
C2—C1—H1A	109.5	C5—C6—H6C	109.5
C2—C1—H1B	109.5	H6A—C6—H6C	109.5
H1A—C1—H1B	109.5	H6B—C6—H6C	109.5
C2—C1—H1C	109.5	C8—C7—N1	122.26 (10)
H1A—C1—H1C	109.5	C8—C7—C12	119.20 (11)
H1B—C1—H1C	109.5	N1—C7—C12	118.51 (11)
O2—C2—C1	107.58 (9)	C9—C8—C7	120.85 (12)
O2—C2—C3	109.08 (8)	C9—C8—H8	119.6
C1—C2—C3	113.24 (10)	C7—C8—H8	119.6
O2—C2—H2	109.0	C10—C9—C8	120.41 (14)
C1—C2—H2	109.0	C10—C9—H9	119.8
C3—C2—H2	109.0	C8—C9—H9	119.8
C4—C3—C2	111.04 (9)	C9—C10—C11	119.03 (14)
C4—C3—H3A	109.4	C9—C10—H10	120.5
C2—C3—H3A	109.4	C11—C10—H10	120.5
C4—C3—H3B	109.4	C10—C11—C12	122.41 (14)
C2—C3—H3B	109.4	C10—C11—H11	118.8
H3A—C3—H3B	108.0	C12—C11—H11	118.8
N1—C4—O1	109.70 (8)	C11—C12—C7	118.09 (13)
N1—C4—C3	111.35 (9)	C11—C12—C13	121.14 (12)
O1—C4—C3	109.23 (8)	C7—C12—C13	120.76 (12)
N1—C4—H4	108.8	C12—C13—H13A	109.5
O1—C4—H4	108.8	C12—C13—H13B	109.5
C3—C4—H4	108.8	H13A—C13—H13B	109.5
O2—C5—O1	111.04 (9)	C12—C13—H13C	109.5
O2—C5—C6	108.50 (10)	H13A—C13—H13C	109.5
O1—C5—C6	108.08 (10)	H13B—C13—H13C	109.5
O2—C5—H5	109.7	C7—N1—C4	121.93 (10)
O1—C5—H5	109.7	C7—N1—H1	115.0 (10)
C6—C5—H5	109.7	C4—N1—H1	112.4 (10)
C5—C6—H6A	109.5	C5—O1—C4	112.35 (8)
C5—C6—H6B	109.5	C5—O2—C2	111.57 (8)
H6A—C6—H6B	109.5
O2—C2—C3—C4	−52.82 (11)	N1—C7—C12—C13	−0.45 (17)
C1—C2—C3—C4	−172.57 (9)	C8—C7—N1—C4	−4.57 (16)
C2—C3—C4—N1	172.86 (8)	C12—C7—N1—C4	177.47 (10)
C2—C3—C4—O1	51.55 (11)	O1—C4—N1—C7	−65.48 (12)
N1—C7—C8—C9	−177.63 (11)	C3—C4—N1—C7	173.48 (9)
C12—C7—C8—C9	0.31 (17)	O2—C5—O1—C4	60.92 (11)
C7—C8—C9—C10	−0.9 (2)	C6—C5—O1—C4	179.82 (9)
C8—C9—C10—C11	0.5 (2)	N1—C4—O1—C5	−177.70 (9)
C9—C10—C11—C12	0.5 (2)	C3—C4—O1—C5	−55.39 (11)
C10—C11—C12—C7	−1.0 (2)	O1—C5—O2—C2	−61.96 (11)
C10—C11—C12—C13	178.05 (14)	C6—C5—O2—C2	179.40 (9)
C8—C7—C12—C11	0.63 (17)	C1—C2—O2—C5	−179.23 (9)
N1—C7—C12—C11	178.65 (11)	C3—C2—O2—C5	57.58 (11)
C8—C7—C12—C13	−178.47 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.843 (15)	2.559 (15)	3.3688 (13)	161.3 (13)
C3—H3A···O1i	0.97	2.54	3.4950 (13)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.843 (15)	2.559 (15)	3.3688 (13)	161.3 (13)
C3—H3A⋯O1i	0.97	2.54	3.4950 (13)	167

Symmetry code: (i) .