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

In the title compound, C12H16BrNO2, the dioxane ring adopts a chair conformation and its mean plane makes a dihedral angle of 60.63 (12)° with the 4-bromo-phenyl ring. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. These dimers are consolidated by pairs of C-H⋯O hydrogen bonds with an R 2 (2)(16) ring motif. Adjacent dimers are connected via C-H⋯O hydrogen bonds, forming infinite chains propagating along the c-axis direction.

Related literature

For biological properties of dioxanes and applications of 1,3-dioxane derivatives, see: Aubele et al. (2005 ▶); Marucci et al. (2005 ▶); Wang et al. (1996a ▶,b ▶); Yuan et al. (2005 ▶). For related crystal structures, see: Chuprunov et al. (1981 ▶); Thevenet et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H16BrNO2

M = 286.17

Monoclinic,

a = 9.9367 (5) Å

b = 13.5660 (6) Å

c = 10.3206 (5) Å

β = 115.543 (3)°

V = 1255.25 (10) Å3

Z = 4

Mo Kα radiation

μ = 3.26 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 = 0.310, T max = 0.746

11981 measured reflections

3119 independent reflections

1819 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.092

S = 1.01

3119 reflections

150 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.38 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/S1600536813025750/su2646sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025750/su2646Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025750/su2646Isup3.cml

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

C12H16BrNO2	F(000) = 584
Mr = 286.17	Dx = 1.514 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3119 reflections
a = 9.9367 (5) Å	θ = 2.3–28.4°
b = 13.5660 (6) Å	µ = 3.26 mm−1
c = 10.3206 (5) Å	T = 293 K
β = 115.543 (3)°	Block, colourless
V = 1255.25 (10) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3119 independent reflections
Radiation source: fine-focus sealed tube	1819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→13
Tmin = 0.310, Tmax = 0.746	k = −18→15
11981 measured reflections	l = −13→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.0602P] where P = (Fo2 + 2Fc2)/3
3119 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.38 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
Br1	1.07805 (3)	0.63232 (2)	1.22087 (3)	0.07742 (15)
O1	0.70096 (17)	0.52265 (9)	0.47016 (15)	0.0474 (4)
O2	0.61959 (17)	0.53559 (10)	0.22317 (15)	0.0488 (4)
N1	0.6108 (2)	0.62162 (13)	0.6010 (2)	0.0502 (5)
H1	0.531 (2)	0.5954 (17)	0.588 (3)	0.060*
C1	0.4240 (3)	0.64080 (17)	0.0718 (3)	0.0640 (7)
H1A	0.4566	0.6270	−0.0014	0.096*
H1B	0.3852	0.7067	0.0598	0.096*
H1C	0.3475	0.5949	0.0642	0.096*
C2	0.5537 (3)	0.63121 (15)	0.2171 (2)	0.0497 (6)
H2	0.6276	0.6818	0.2260	0.060*
C3	0.5121 (3)	0.64209 (15)	0.3411 (3)	0.0504 (6)
H3A	0.4781	0.7088	0.3433	0.060*
H3B	0.4311	0.5973	0.3282	0.060*
C4	0.6445 (3)	0.61968 (14)	0.4810 (2)	0.0461 (5)
H4	0.7225	0.6685	0.4960	0.055*
C5	0.7436 (3)	0.51969 (17)	0.3564 (2)	0.0522 (6)
H5	0.8196	0.5701	0.3714	0.063*
C6	0.8065 (3)	0.4193 (2)	0.3537 (3)	0.0756 (8)
H6A	0.8360	0.4162	0.2766	0.113*
H6B	0.7320	0.3701	0.3394	0.113*
H6C	0.8917	0.4075	0.4432	0.113*
C7	0.7211 (3)	0.62384 (13)	0.7422 (2)	0.0433 (5)
C8	0.6828 (3)	0.60493 (15)	0.8537 (3)	0.0501 (6)
H8	0.5844	0.5896	0.8328	0.060*
C9	0.7872 (3)	0.60831 (15)	0.9954 (3)	0.0545 (6)
H9	0.7594	0.5944	1.0687	0.065*
C10	0.9320 (3)	0.63231 (14)	1.0272 (3)	0.0504 (6)
C11	0.9719 (3)	0.65323 (19)	0.9185 (3)	0.0622 (7)
H11	1.0698	0.6707	0.9402	0.075*
C12	0.8674 (3)	0.64851 (18)	0.7771 (3)	0.0586 (6)
H12	0.8960	0.6622	0.7042	0.070*

	U11	U22	U33	U12	U13	U23
Br1	0.0657 (2)	0.1039 (3)	0.05105 (18)	0.01315 (15)	0.01413 (14)	−0.00249 (14)
O1	0.0466 (10)	0.0523 (8)	0.0450 (8)	0.0057 (7)	0.0215 (7)	0.0021 (7)
O2	0.0433 (9)	0.0577 (9)	0.0437 (9)	−0.0010 (7)	0.0170 (7)	−0.0041 (7)
N1	0.0444 (12)	0.0600 (12)	0.0494 (11)	−0.0045 (9)	0.0232 (10)	−0.0055 (9)
C1	0.0644 (18)	0.0693 (16)	0.0515 (15)	0.0022 (13)	0.0185 (13)	0.0100 (12)
C2	0.0489 (15)	0.0482 (13)	0.0496 (13)	−0.0078 (10)	0.0189 (12)	0.0034 (10)
C3	0.0513 (15)	0.0458 (12)	0.0521 (14)	0.0051 (11)	0.0205 (12)	0.0013 (10)
C4	0.0472 (14)	0.0483 (12)	0.0449 (12)	−0.0050 (10)	0.0218 (11)	−0.0036 (10)
C5	0.0410 (14)	0.0714 (15)	0.0454 (13)	−0.0020 (11)	0.0199 (11)	−0.0053 (11)
C6	0.067 (2)	0.0956 (19)	0.0612 (17)	0.0282 (16)	0.0250 (15)	−0.0049 (15)
C7	0.0451 (14)	0.0386 (11)	0.0480 (12)	0.0019 (10)	0.0219 (11)	−0.0023 (9)
C8	0.0457 (15)	0.0546 (12)	0.0556 (14)	−0.0051 (11)	0.0273 (12)	−0.0005 (11)
C9	0.0614 (18)	0.0605 (14)	0.0499 (13)	0.0015 (12)	0.0319 (13)	0.0046 (11)
C10	0.0494 (15)	0.0528 (13)	0.0471 (13)	0.0079 (11)	0.0190 (11)	−0.0007 (10)
C11	0.0418 (15)	0.0861 (17)	0.0596 (16)	−0.0025 (12)	0.0226 (13)	−0.0010 (13)
C12	0.0468 (15)	0.0854 (17)	0.0514 (15)	−0.0032 (13)	0.0284 (12)	0.0014 (12)

Br1—C10	1.898 (2)	C4—H4	0.9800
O1—C5	1.410 (2)	C5—C6	1.504 (3)
O1—C4	1.454 (2)	C5—H5	0.9800
O2—C5	1.412 (3)	C6—H6A	0.9600
O2—C2	1.442 (2)	C6—H6B	0.9600
N1—C7	1.396 (3)	C6—H6C	0.9600
N1—C4	1.416 (3)	C7—C12	1.379 (3)
N1—H1	0.824 (16)	C7—C8	1.383 (3)
C1—C2	1.503 (3)	C8—C9	1.382 (3)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—C10	1.369 (4)
C1—H1C	0.9600	C9—H9	0.9300
C2—C3	1.513 (3)	C10—C11	1.371 (3)
C2—H2	0.9800	C11—C12	1.381 (4)
C3—C4	1.507 (3)	C11—H11	0.9300
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700
C5—O1—C4	110.76 (15)	O1—C5—C6	108.55 (19)
C5—O2—C2	111.66 (16)	O2—C5—C6	108.37 (19)
C7—N1—C4	122.5 (2)	O1—C5—H5	109.7
C7—N1—H1	116.7 (18)	O2—C5—H5	109.7
C4—N1—H1	114.8 (18)	C6—C5—H5	109.7
C2—C1—H1A	109.5	C5—C6—H6A	109.5
C2—C1—H1B	109.5	C5—C6—H6B	109.5
H1A—C1—H1B	109.5	H6A—C6—H6B	109.5
C2—C1—H1C	109.5	C5—C6—H6C	109.5
H1A—C1—H1C	109.5	H6A—C6—H6C	109.5
H1B—C1—H1C	109.5	H6B—C6—H6C	109.5
O2—C2—C1	107.42 (17)	C12—C7—C8	117.7 (2)
O2—C2—C3	109.59 (17)	C12—C7—N1	122.8 (2)
C1—C2—C3	114.0 (2)	C8—C7—N1	119.4 (2)
O2—C2—H2	108.6	C9—C8—C7	121.6 (2)
C1—C2—H2	108.6	C9—C8—H8	119.2
C3—C2—H2	108.6	C7—C8—H8	119.2
C4—C3—C2	110.3 (2)	C10—C9—C8	119.6 (2)
C4—C3—H3A	109.6	C10—C9—H9	120.2
C2—C3—H3A	109.6	C8—C9—H9	120.2
C4—C3—H3B	109.6	C9—C10—C11	119.9 (2)
C2—C3—H3B	109.6	C9—C10—Br1	119.97 (18)
H3A—C3—H3B	108.1	C11—C10—Br1	120.13 (19)
N1—C4—O1	109.21 (16)	C10—C11—C12	120.3 (2)
N1—C4—C3	113.3 (2)	C10—C11—H11	119.9
O1—C4—C3	108.37 (17)	C12—C11—H11	119.9
N1—C4—H4	108.6	C7—C12—C11	121.0 (2)
O1—C4—H4	108.6	C7—C12—H12	119.5
C3—C4—H4	108.6	C11—C12—H12	119.5
O1—C5—O2	110.92 (17)
C5—O2—C2—C1	179.79 (18)	C2—O2—C5—C6	−179.48 (18)
C5—O2—C2—C3	−55.9 (2)	C4—N1—C7—C12	16.4 (3)
O2—C2—C3—C4	53.0 (2)	C4—N1—C7—C8	−166.52 (18)
C1—C2—C3—C4	173.36 (17)	C12—C7—C8—C9	−1.4 (3)
C7—N1—C4—O1	73.0 (2)	N1—C7—C8—C9	−178.59 (18)
C7—N1—C4—C3	−166.05 (17)	C7—C8—C9—C10	1.0 (3)
C5—O1—C4—N1	−176.72 (18)	C8—C9—C10—C11	0.3 (3)
C5—O1—C4—C3	59.4 (2)	C8—C9—C10—Br1	−177.60 (15)
C2—C3—C4—N1	−175.78 (17)	C9—C10—C11—C12	−1.1 (4)
C2—C3—C4—O1	−54.4 (2)	Br1—C10—C11—C12	176.77 (18)
C4—O1—C5—O2	−63.2 (2)	C8—C7—C12—C11	0.6 (3)
C4—O1—C5—C6	177.81 (19)	N1—C7—C12—C11	177.6 (2)
C2—O2—C5—O1	61.5 (2)	C10—C11—C12—C7	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.82 (2)	2.66 (2)	3.465 (2)	168 (2)
C8—H8···O2i	0.93	2.51	3.352 (3)	150
C9—H9···O2ii	0.93	2.65	3.557 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.82 (2)	2.66 (2)	3.465 (2)	168 (2)
C8—H8⋯O2i	0.93	2.51	3.352 (3)	150
C9—H9⋯O2ii	0.93	2.65	3.557 (3)	165

Symmetry codes: (i) ; (ii) .