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

In the title compound, C12H16FNO2, the dioxane ring adopts a chair conformation with the methyl substituents and the C-N bond in equatorial orientations. Its mean plane subtends a dihedral angle of 40.17 (6)° with the benzene ring. In the crystal, weak N-H⋯F hydrogen bonds link the mol-ecules into C(7) chains propagating in [100].

Related literature

For a related structure and background to dioxanes, see: Fatima et al. (2013 ▶).

Experimental

Crystal data

C12H16FNO2

M = 225.26

Monoclinic,

a = 10.4924 (10) Å

b = 10.0614 (10) Å

c = 11.0379 (11) Å

β = 90.136 (2)°

V = 1165.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.649, T max = 0.746

10977 measured reflections

2910 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.129

S = 1.01

2910 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 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/S1600536813026561/hb7138sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026561/hb7138Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026561/hb7138Isup3.cml

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

C12H16FNO2	F(000) = 480
Mr = 225.26	Dx = 1.284 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2910 reflections
a = 10.4924 (10) Å	θ = 2.7–28.4°
b = 10.0614 (10) Å	µ = 0.10 mm−1
c = 11.0379 (11) Å	T = 293 K
β = 90.136 (2)°	Block, colourless
V = 1165.2 (2) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2910 independent reflections
Radiation source: fine-focus sealed tube	2179 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scans	θmax = 28.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.649, Tmax = 0.746	k = −13→13
10977 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.1851P] where P = (Fo2 + 2Fc2)/3
2910 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 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
O1	0.85420 (8)	0.16432 (8)	0.95248 (8)	0.0469 (2)
O2	0.91002 (9)	0.28191 (9)	0.77911 (8)	0.0509 (2)
C3	0.91619 (12)	0.04131 (13)	0.77606 (11)	0.0491 (3)
H3A	0.8970	−0.0356	0.7263	0.059*
H3B	1.0045	0.0351	0.8018	0.059*
C5	0.82700 (12)	0.27629 (12)	0.87937 (12)	0.0482 (3)
H5	0.7386	0.2718	0.8509	0.058*
N1	0.84979 (10)	−0.06797 (11)	0.96310 (10)	0.0525 (3)
H1	0.9177	−0.1148	0.9546	0.063*
C4	0.83024 (11)	0.04228 (11)	0.88605 (11)	0.0453 (3)
H4	0.7413	0.0421	0.8587	0.054*
C2	0.89697 (13)	0.16759 (13)	0.70224 (12)	0.0514 (3)
H2	0.8111	0.1669	0.6672	0.062*
F1	0.49573 (9)	−0.21970 (11)	1.30521 (8)	0.0788 (3)
C7	0.76261 (11)	−0.10329 (11)	1.05237 (11)	0.0442 (3)
C8	0.77421 (13)	−0.22492 (13)	1.11186 (14)	0.0556 (3)
H8	0.8424	−0.2806	1.0939	0.067*
C9	0.68551 (15)	−0.26374 (15)	1.19728 (14)	0.0622 (4)
H9	0.6935	−0.3450	1.2367	0.075*
C12	0.66199 (11)	−0.02028 (12)	1.08440 (12)	0.0497 (3)
H12	0.6546	0.0628	1.0481	0.060*
C11	0.57272 (13)	−0.05951 (14)	1.16951 (12)	0.0539 (3)
H11	0.5051	−0.0041	1.1898	0.065*
C6	0.84563 (15)	0.39947 (14)	0.95358 (14)	0.0630 (4)
H6A	0.9318	0.4026	0.9830	0.095*
H6B	0.7879	0.3985	1.0209	0.095*
H6C	0.8292	0.4763	0.9044	0.095*
C10	0.58580 (13)	−0.18076 (15)	1.22298 (12)	0.0553 (3)
C1	0.99285 (17)	0.18267 (17)	0.60184 (14)	0.0693 (4)
H1A	0.9765	0.2637	0.5585	0.104*
H1B	0.9860	0.1086	0.5474	0.104*
H1C	1.0772	0.1854	0.6357	0.104*

	U11	U22	U33	U12	U13	U23
O1	0.0494 (5)	0.0386 (4)	0.0529 (5)	−0.0015 (3)	−0.0005 (4)	0.0021 (3)
O2	0.0567 (5)	0.0407 (5)	0.0551 (5)	−0.0081 (4)	−0.0008 (4)	0.0033 (4)
C3	0.0510 (7)	0.0415 (6)	0.0550 (7)	−0.0041 (5)	0.0010 (5)	−0.0027 (5)
C5	0.0448 (6)	0.0382 (6)	0.0615 (7)	0.0007 (5)	−0.0030 (5)	0.0043 (5)
N1	0.0438 (5)	0.0426 (5)	0.0712 (7)	0.0076 (4)	0.0087 (5)	0.0123 (5)
C4	0.0402 (6)	0.0372 (6)	0.0584 (7)	−0.0023 (4)	−0.0015 (5)	0.0035 (5)
C2	0.0558 (7)	0.0469 (7)	0.0514 (7)	−0.0082 (5)	−0.0057 (6)	0.0004 (5)
F1	0.0799 (6)	0.0875 (7)	0.0691 (6)	−0.0231 (5)	0.0156 (5)	0.0142 (5)
C7	0.0412 (6)	0.0360 (6)	0.0555 (7)	−0.0029 (4)	−0.0031 (5)	0.0024 (5)
C8	0.0480 (7)	0.0442 (7)	0.0747 (9)	0.0025 (5)	−0.0051 (6)	0.0114 (6)
C9	0.0643 (8)	0.0516 (7)	0.0705 (9)	−0.0076 (6)	−0.0097 (7)	0.0214 (7)
C12	0.0499 (6)	0.0372 (6)	0.0621 (7)	0.0001 (5)	0.0030 (5)	0.0039 (5)
C11	0.0503 (7)	0.0510 (7)	0.0603 (8)	−0.0029 (5)	0.0048 (6)	−0.0042 (6)
C6	0.0729 (9)	0.0416 (7)	0.0746 (9)	−0.0004 (6)	0.0029 (7)	−0.0027 (6)
C10	0.0554 (7)	0.0602 (8)	0.0502 (7)	−0.0158 (6)	0.0003 (6)	0.0050 (6)
C1	0.0872 (11)	0.0654 (9)	0.0554 (8)	−0.0120 (8)	0.0075 (8)	0.0026 (7)

O1—C5	1.4145 (14)	C7—C8	1.3940 (17)
O1—C4	1.4517 (14)	C7—C12	1.3924 (17)
O2—C5	1.4111 (16)	C8—C9	1.383 (2)
O2—C2	1.4357 (15)	C8—H8	0.9300
C3—C4	1.5141 (17)	C9—C10	1.369 (2)
C3—C2	1.5226 (18)	C9—H9	0.9300
C3—H3A	0.9700	C12—C11	1.3856 (17)
C3—H3B	0.9700	C12—H12	0.9300
C5—C6	1.4981 (19)	C11—C10	1.362 (2)
C5—H5	0.9800	C11—H11	0.9300
N1—C7	1.3922 (15)	C6—H6A	0.9600
N1—C4	1.4125 (15)	C6—H6B	0.9600
N1—H1	0.8600	C6—H6C	0.9600
C4—H4	0.9800	C1—H1A	0.9600
C2—C1	1.5061 (19)	C1—H1B	0.9600
C2—H2	0.9800	C1—H1C	0.9600
F1—C10	1.3691 (15)
C5—O1—C4	110.55 (9)	C8—C7—C12	118.19 (12)
C5—O2—C2	111.92 (9)	N1—C7—C12	121.77 (11)
C4—C3—C2	110.20 (10)	C9—C8—C7	120.73 (13)
C4—C3—H3A	109.6	C9—C8—H8	119.6
C2—C3—H3A	109.6	C7—C8—H8	119.6
C4—C3—H3B	109.6	C10—C9—C8	119.02 (13)
C2—C3—H3B	109.6	C10—C9—H9	120.5
H3A—C3—H3B	108.1	C8—C9—H9	120.5
O2—C5—O1	110.80 (9)	C11—C12—C7	121.03 (12)
O2—C5—C6	108.40 (10)	C11—C12—H12	119.5
O1—C5—C6	108.73 (11)	C7—C12—H12	119.5
O2—C5—H5	109.6	C10—C11—C12	118.78 (13)
O1—C5—H5	109.6	C10—C11—H11	120.6
C6—C5—H5	109.6	C12—C11—H11	120.6
C7—N1—C4	122.13 (10)	C5—C6—H6A	109.5
C7—N1—H1	118.9	C5—C6—H6B	109.5
C4—N1—H1	118.9	H6A—C6—H6B	109.5
N1—C4—O1	109.60 (10)	C5—C6—H6C	109.5
N1—C4—C3	113.06 (10)	H6A—C6—H6C	109.5
O1—C4—C3	107.92 (9)	H6B—C6—H6C	109.5
N1—C4—H4	108.7	C11—C10—C9	122.19 (12)
O1—C4—H4	108.7	C11—C10—F1	118.33 (13)
C3—C4—H4	108.7	C9—C10—F1	119.47 (13)
O2—C2—C1	106.93 (10)	C2—C1—H1A	109.5
O2—C2—C3	109.87 (10)	C2—C1—H1B	109.5
C1—C2—C3	112.96 (12)	H1A—C1—H1B	109.5
O2—C2—H2	109.0	C2—C1—H1C	109.5
C1—C2—H2	109.0	H1A—C1—H1C	109.5
C3—C2—H2	109.0	H1B—C1—H1C	109.5
C8—C7—N1	120.04 (11)
C2—O2—C5—O1	61.43 (13)	C4—C3—C2—C1	171.55 (11)
C2—O2—C5—C6	−179.33 (10)	C4—N1—C7—C8	168.84 (12)
C4—O1—C5—O2	−64.23 (12)	C4—N1—C7—C12	−10.76 (19)
C4—O1—C5—C6	176.73 (10)	N1—C7—C8—C9	−177.40 (13)
C7—N1—C4—O1	74.98 (14)	C12—C7—C8—C9	2.2 (2)
C7—N1—C4—C3	−164.58 (11)	C7—C8—C9—C10	−0.1 (2)
C5—O1—C4—N1	−176.11 (9)	C8—C7—C12—C11	−2.58 (19)
C5—O1—C4—C3	60.37 (12)	N1—C7—C12—C11	177.03 (12)
C2—C3—C4—N1	−175.84 (10)	C7—C12—C11—C10	0.8 (2)
C2—C3—C4—O1	−54.45 (12)	C12—C11—C10—C9	1.4 (2)
C5—O2—C2—C1	−178.06 (10)	C12—C11—C10—F1	−178.74 (12)
C5—O2—C2—C3	−55.13 (13)	C8—C9—C10—C11	−1.7 (2)
C4—C3—C2—O2	52.25 (14)	C8—C9—C10—F1	178.39 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F1i	0.86	2.48	3.1556 (14)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯F1i	0.86	2.48	3.1556 (14)	136

Symmetry code: (i) .