N-(2-Fluoro-phen-yl)-2,6-dimethyl-1,3-dioxan-4-amine.

In the title compound, C12H16FNO3, the dioxane ring adopts a chair conformation with the methyl groups and amine N atom in equatorial positions. The best plane through the dioxane ring makes a dihedral angle of 43.16 (8)° with the phenyl ring. In the crystal, pairs of C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric R 2 (2)(8) dimers, which are linked into [100] chains by further C-H⋯O hydrogen bonds. The N-H group does not participate in hydrogen bonding.

Related literature

Dioxane rings are frequently encountered in structural motifs in many bioactive mol­ecules such as cytotoxic agents (Aubele et al., 2005 ▶) and anti­muscarinic agents (Marucci et al., 2005 ▶). For applications of this class of compounds, see: Wang, Yuan, Liu et al. (1996 ▶); Wang, Yuan, Lei & Liu (1996 ▶); Yuan et al. (2005 ▶). For related crystal structures, see: Chuprunov et al. (1981 ▶).

Experimental

Crystal data

C12H16FNO2

M = 225.26

Monoclinic,

a = 19.6219 (13) Å

b = 8.1603 (6) Å

c = 15.2396 (10) Å

β = 95.950 (3)°

V = 2427.0 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.617, T max = 0.746

11540 measured reflections

3020 independent reflections

1973 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 1.03

3020 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.23 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813024732/hb7132sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024732/hb7132Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024732/hb7132Isup3.cml

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

C12H16FNO2	F(000) = 960
Mr = 225.26	Dx = 1.233 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3020 reflections
a = 19.6219 (13) Å	θ = 2.7–28.4°
b = 8.1603 (6) Å	µ = 0.09 mm−1
c = 15.2396 (10) Å	T = 293 K
β = 95.950 (3)°	Block, colourless
V = 2427.0 (3) Å3	0.25 × 0.20 × 0.15 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	3020 independent reflections
Radiation source: fine-focus sealed tube	1973 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 28.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −26→25
Tmin = 0.617, Tmax = 0.746	k = −10→10
11540 measured reflections	l = −17→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.5739P] where P = (Fo2 + 2Fc2)/3
3020 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	−0.0550 (9)	0.220 (2)	1.0096 (12)	0.074 (5)*
H3	0.1172 (8)	0.1912 (19)	0.8533 (10)	0.058 (4)*
O1	0.13369 (5)	0.02783 (12)	0.94558 (6)	0.0592 (3)
O2	0.02809 (4)	0.13036 (11)	0.88947 (6)	0.0535 (3)
C4	0.02808 (7)	0.25397 (16)	0.95733 (9)	0.0526 (3)
H4	0.0476	0.3552	0.9360	0.063*
C5	0.07197 (7)	0.19735 (17)	1.03878 (9)	0.0545 (3)
H5A	0.0500	0.1056	1.0649	0.065*
H5B	0.0767	0.2854	1.0817	0.065*
N1	−0.04050 (7)	0.28505 (17)	0.97514 (9)	0.0617 (3)
C2	0.14205 (7)	0.14617 (18)	1.01572 (9)	0.0561 (3)
H2	0.1657	0.2425	0.9953	0.067*
C3	0.09501 (7)	0.0917 (2)	0.87025 (9)	0.0562 (4)
C7	−0.08824 (7)	0.35496 (17)	0.91321 (10)	0.0598 (4)
F1	−0.16772 (6)	0.33920 (15)	1.01790 (9)	0.1024 (4)
C6	0.09070 (10)	−0.0353 (3)	0.79920 (11)	0.0828 (6)
H6A	0.1360	−0.0620	0.7852	0.124*
H6B	0.0642	0.0064	0.7475	0.124*
H6C	0.0691	−0.1320	0.8192	0.124*
C12	−0.15451 (8)	0.3829 (2)	0.93551 (13)	0.0723 (5)
C1	0.18616 (9)	0.0692 (2)	1.09141 (10)	0.0745 (5)
H1A	0.2296	0.0394	1.0725	0.112*
H1B	0.1639	−0.0270	1.1108	0.112*
H1C	0.1931	0.1460	1.1392	0.112*
C8	−0.07505 (9)	0.4054 (2)	0.83014 (11)	0.0733 (5)
H8	−0.0318	0.3885	0.8120	0.088*
C9	−0.12519 (11)	0.4808 (2)	0.77326 (12)	0.0899 (6)
H9	−0.1151	0.5158	0.7180	0.108*
C11	−0.20465 (10)	0.4542 (3)	0.88042 (17)	0.0926 (7)
H11	−0.2482	0.4692	0.8979	0.111*
C10	−0.18988 (12)	0.5039 (3)	0.79822 (16)	0.0989 (7)
H10	−0.2236	0.5532	0.7596	0.119*

	U11	U22	U33	U12	U13	U23
O1	0.0587 (6)	0.0740 (6)	0.0451 (5)	0.0204 (5)	0.0063 (4)	−0.0013 (4)
O2	0.0435 (5)	0.0652 (5)	0.0531 (5)	0.0060 (4)	0.0112 (4)	−0.0052 (4)
C4	0.0477 (8)	0.0510 (7)	0.0608 (8)	0.0028 (6)	0.0144 (6)	−0.0025 (6)
C5	0.0596 (9)	0.0530 (7)	0.0523 (8)	0.0005 (6)	0.0128 (6)	−0.0070 (6)
N1	0.0521 (7)	0.0665 (7)	0.0695 (8)	0.0106 (6)	0.0208 (6)	−0.0006 (7)
C2	0.0533 (8)	0.0627 (8)	0.0526 (8)	0.0015 (6)	0.0068 (6)	0.0016 (6)
C3	0.0474 (8)	0.0767 (9)	0.0461 (7)	0.0128 (7)	0.0113 (6)	0.0061 (7)
C7	0.0516 (8)	0.0563 (7)	0.0721 (10)	0.0061 (6)	0.0093 (7)	−0.0185 (7)
F1	0.0756 (7)	0.1085 (8)	0.1316 (10)	0.0213 (6)	0.0513 (7)	0.0091 (7)
C6	0.0734 (11)	0.1247 (15)	0.0507 (8)	0.0338 (10)	0.0076 (8)	−0.0165 (9)
C12	0.0542 (9)	0.0690 (9)	0.0948 (12)	0.0079 (7)	0.0129 (9)	−0.0202 (9)
C1	0.0746 (11)	0.0911 (11)	0.0554 (9)	0.0164 (9)	−0.0043 (8)	−0.0047 (8)
C8	0.0689 (10)	0.0814 (10)	0.0697 (10)	0.0192 (8)	0.0081 (8)	−0.0148 (8)
C9	0.1005 (16)	0.0957 (13)	0.0703 (11)	0.0248 (11)	−0.0069 (10)	−0.0226 (10)
C11	0.0544 (10)	0.0973 (13)	0.1236 (18)	0.0145 (9)	−0.0033 (11)	−0.0348 (13)
C10	0.0798 (14)	0.1034 (14)	0.1047 (16)	0.0290 (11)	−0.0316 (12)	−0.0404 (13)

O1—C3	1.4087 (16)	C7—C12	1.396 (2)
O1—C2	1.4373 (17)	F1—C12	1.356 (2)
O2—C3	1.4105 (16)	C6—H6A	0.9600
O2—C4	1.4446 (16)	C6—H6B	0.9600
C4—N1	1.4228 (17)	C6—H6C	0.9600
C4—C5	1.508 (2)	C12—C11	1.357 (3)
C4—H4	0.9800	C1—H1A	0.9600
C5—C2	1.513 (2)	C1—H1B	0.9600
C5—H5A	0.9700	C1—H1C	0.9600
C5—H5B	0.9700	C8—C9	1.386 (2)
N1—C7	1.382 (2)	C8—H8	0.9300
N1—H1	0.820 (18)	C9—C10	1.375 (3)
C2—C1	1.506 (2)	C9—H9	0.9300
C2—H2	0.9800	C11—C10	1.376 (3)
C3—C6	1.495 (2)	C11—H11	0.9300
C3—H3	0.969 (16)	C10—H10	0.9300
C7—C8	1.381 (2)
C3—O1—C2	111.59 (11)	C8—C7—C12	116.24 (16)
C3—O2—C4	111.98 (10)	N1—C7—C12	118.92 (15)
N1—C4—O2	109.35 (11)	C3—C6—H6A	109.5
N1—C4—C5	111.61 (11)	C3—C6—H6B	109.5
O2—C4—C5	109.44 (10)	H6A—C6—H6B	109.5
N1—C4—H4	108.8	C3—C6—H6C	109.5
O2—C4—H4	108.8	H6A—C6—H6C	109.5
C5—C4—H4	108.8	H6B—C6—H6C	109.5
C4—C5—C2	110.40 (11)	F1—C12—C11	119.33 (17)
C4—C5—H5A	109.6	F1—C12—C7	117.05 (16)
C2—C5—H5A	109.6	C11—C12—C7	123.6 (2)
C4—C5—H5B	109.6	C2—C1—H1A	109.5
C2—C5—H5B	109.6	C2—C1—H1B	109.5
H5A—C5—H5B	108.1	H1A—C1—H1B	109.5
C7—N1—C4	122.05 (13)	C2—C1—H1C	109.5
C7—N1—H1	116.8 (13)	H1A—C1—H1C	109.5
C4—N1—H1	113.9 (13)	H1B—C1—H1C	109.5
O1—C2—C1	107.55 (12)	C7—C8—C9	121.15 (18)
O1—C2—C5	108.78 (11)	C7—C8—H8	119.4
C1—C2—C5	113.66 (12)	C9—C8—H8	119.4
O1—C2—H2	108.9	C10—C9—C8	120.2 (2)
C1—C2—H2	108.9	C10—C9—H9	119.9
C5—C2—H2	108.9	C8—C9—H9	119.9
O1—C3—O2	110.36 (10)	C12—C11—C10	118.84 (19)
O1—C3—C6	108.61 (13)	C12—C11—H11	120.6
O2—C3—C6	108.76 (13)	C10—C11—H11	120.6
O1—C3—H3	107.9 (9)	C9—C10—C11	119.91 (19)
O2—C3—H3	108.7 (9)	C9—C10—H10	120.0
C6—C3—H3	112.5 (9)	C11—C10—H10	120.0
C8—C7—N1	124.81 (14)
C3—O2—C4—N1	−178.72 (11)	C4—N1—C7—C8	−1.8 (2)
C3—O2—C4—C5	−56.18 (14)	C4—N1—C7—C12	−179.59 (13)
N1—C4—C5—C2	173.31 (11)	C8—C7—C12—F1	−177.83 (14)
O2—C4—C5—C2	52.12 (15)	N1—C7—C12—F1	0.2 (2)
O2—C4—N1—C7	−65.93 (17)	C8—C7—C12—C11	0.4 (2)
C5—C4—N1—C7	172.83 (12)	N1—C7—C12—C11	178.40 (16)
C3—O1—C2—C1	−177.76 (12)	N1—C7—C8—C9	−177.28 (16)
C3—O1—C2—C5	58.73 (14)	C12—C7—C8—C9	0.6 (2)
C4—C5—C2—O1	−53.33 (14)	C7—C8—C9—C10	−1.2 (3)
C4—C5—C2—C1	−173.11 (12)	F1—C12—C11—C10	177.44 (17)
C2—O1—C3—O2	−62.98 (16)	C7—C12—C11—C10	−0.7 (3)
C2—O1—C3—C6	177.87 (13)	C8—C9—C10—C11	0.9 (3)
C4—O2—C3—O1	61.46 (15)	C12—C11—C10—C9	0.1 (3)
C4—O2—C3—C6	−179.49 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2i	0.97	2.60	3.5563 (17)	169
C11—H11···O1ii	0.93	2.54	3.473 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2i	0.97	2.60	3.5563 (17)	169
C11—H11⋯O1ii	0.93	2.54	3.473 (2)	177

Symmetry codes: (i) ; (ii) .