3,3'-(Ethane-1,2-di-yl)bis-(6-methyl-3,4-dihydro-2H-1,3-benzoxazine).

The asymmetric unit of the title compound, C(20)H(24)N(2)O(2), contains one half-mol-ecule, which is completed by inversion symmetry. In the crystal, mol-ecular chains are formed through non-classical C-H⋯O hydrogen bonds, formed between axial H atoms of the oxazine ring and a O atom of a neighboring mol-ecule.

Related literature

For the synthesis, see: Rivera et al. (1994 ▶). For a related structure, see: Rivera et al. (2010 ▶). For uses of benzoxazines in polymer science, see Yaggi et al. (2009 ▶). For the biological activity of bis-benzoxazine compounds, see: Billmann & Dorman (1963 ▶); Heinisch et al. (2002 ▶).

Experimental

Crystal data

C20H24N2O2

M = 324.41

Monoclinic,

a = 8.5042 (1) Å

b = 5.8558 (1) Å

c = 16.5519 (2) Å

β = 95.899 (1)°

V = 819.90 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.68 mm−1

T = 130 K

0.50 × 0.33 × 0.20 mm

Data collection

Xcalibur, Atlas, Gemini ultra diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.384, T max = 0.668

7156 measured reflections

1452 independent reflections

1429 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.087

S = 1.03

1452 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027139/qm2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027139/qm2015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027139/qm2015Isup3.cml

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

C20H24N2O2	F(000) = 348
Mr = 324.41	Dx = 1.314 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 6632 reflections
a = 8.5042 (1) Å	θ = 5.2–67.0°
b = 5.8558 (1) Å	µ = 0.68 mm−1
c = 16.5519 (2) Å	T = 130 K
β = 95.899 (1)°	Plate, colourless
V = 819.90 (2) Å3	0.50 × 0.33 × 0.20 mm
Z = 2

Xcalibur, Atlas, Gemini ultra diffractometer	1452 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1429 reflections with I > 2σ(I)
mirror	Rint = 0.013
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 5.4°
Rotation method data acquisition using ω scans	h = −10→10
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	k = −7→6
Tmin = 0.384, Tmax = 0.668	l = −18→19
7156 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.3441P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1452 reflections	Δρmax = 0.21 e Å−3
111 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (2)

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. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*Ueq of the parent atom.

	x	y	z	Uiso*/Ueq
O1	0.72879 (9)	0.13355 (13)	0.81920 (5)	0.0219 (2)
C2	0.88891 (13)	0.0460 (2)	0.82084 (7)	0.0207 (3)
H2A	0.8959	−0.0491	0.7734	0.025*
H2B	0.9608	0.1735	0.8174	0.025*
N3	0.93877 (10)	−0.08416 (16)	0.89191 (5)	0.0191 (3)
C4	0.84012 (13)	−0.29037 (19)	0.89165 (6)	0.0196 (3)
H4A	0.8583	−0.3650	0.9441	0.023*
H4B	0.8708	−0.3956	0.8508	0.023*
C5	0.66601 (13)	−0.23570 (19)	0.87416 (6)	0.0189 (3)
C6	0.54855 (13)	−0.3874 (2)	0.89236 (6)	0.0205 (3)
H6	0.5781	−0.5261	0.9168	0.025*
C7	0.38861 (13)	−0.3384 (2)	0.87522 (7)	0.0220 (3)
C8	0.34747 (13)	−0.1288 (2)	0.83884 (7)	0.0245 (3)
H8	0.2412	−0.0917	0.8271	0.029*
C9	0.46154 (14)	0.0245 (2)	0.81998 (7)	0.0232 (3)
H9	0.4319	0.1630	0.7955	0.028*
C10	0.62084 (13)	−0.02829 (19)	0.83767 (6)	0.0195 (3)
C11	0.26270 (14)	−0.5038 (2)	0.89513 (7)	0.0261 (3)
H11A	0.2123	−0.5685	0.8458	0.031*
H11B	0.1856	−0.4250	0.9232	0.031*
H11C	0.3099	−0.6234	0.9291	0.031*
C12	0.94008 (13)	0.04830 (19)	0.96715 (6)	0.0205 (3)
H12A	0.8357	0.0451	0.9858	0.025*
H12B	0.9662	0.2060	0.9566	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0200 (4)	0.0209 (4)	0.0243 (4)	0.0001 (3)	0.0000 (3)	0.0041 (3)
C2	0.0187 (5)	0.0238 (6)	0.0194 (6)	−0.0003 (4)	0.0012 (4)	0.0010 (4)
N3	0.0195 (5)	0.0195 (5)	0.0180 (5)	−0.0007 (4)	0.0001 (4)	−0.0003 (4)
C4	0.0204 (6)	0.0183 (6)	0.0195 (5)	0.0008 (4)	0.0001 (4)	−0.0005 (4)
C5	0.0202 (6)	0.0207 (6)	0.0155 (5)	0.0008 (4)	0.0003 (4)	−0.0030 (4)
C6	0.0238 (6)	0.0195 (6)	0.0179 (5)	0.0005 (4)	0.0010 (4)	−0.0018 (4)
C7	0.0217 (6)	0.0251 (6)	0.0193 (5)	−0.0018 (5)	0.0028 (4)	−0.0048 (5)
C8	0.0176 (6)	0.0291 (7)	0.0263 (6)	0.0026 (5)	0.0000 (4)	−0.0029 (5)
C9	0.0234 (6)	0.0217 (6)	0.0239 (6)	0.0035 (5)	−0.0008 (4)	0.0004 (5)
C10	0.0212 (6)	0.0209 (6)	0.0164 (5)	−0.0013 (4)	0.0012 (4)	−0.0023 (4)
C11	0.0216 (6)	0.0295 (7)	0.0275 (6)	−0.0021 (5)	0.0040 (5)	−0.0023 (5)
C12	0.0205 (5)	0.0196 (6)	0.0208 (6)	0.0012 (4)	−0.0007 (4)	−0.0017 (4)

O1—C10	1.3755 (14)	C6—H6	0.9300
O1—C2	1.4525 (13)	C7—C8	1.3958 (18)
C2—N3	1.4291 (14)	C7—C11	1.5052 (16)
C2—H2A	0.9700	C8—C9	1.3808 (17)
C2—H2B	0.9700	C8—H8	0.9300
N3—C12	1.4663 (14)	C9—C10	1.3910 (16)
N3—C4	1.4701 (14)	C9—H9	0.9300
C4—C5	1.5134 (15)	C11—H11A	0.9600
C4—H4A	0.9700	C11—H11B	0.9600
C4—H4B	0.9700	C11—H11C	0.9600
C5—C6	1.3926 (16)	C12—C12i	1.521 (2)
C5—C10	1.3928 (16)	C12—H12A	0.9700
C6—C7	1.3905 (16)	C12—H12B	0.9700
C10—O1—C2	113.49 (8)	C6—C7—C11	121.71 (11)
N3—C2—O1	113.69 (8)	C8—C7—C11	120.52 (10)
N3—C2—H2A	108.8	C9—C8—C7	121.23 (10)
O1—C2—H2A	108.8	C9—C8—H8	119.4
N3—C2—H2B	108.8	C7—C8—H8	119.4
O1—C2—H2B	108.8	C8—C9—C10	119.98 (11)
H2A—C2—H2B	107.7	C8—C9—H9	120.0
C2—N3—C12	113.12 (9)	C10—C9—H9	120.0
C2—N3—C4	108.35 (8)	O1—C10—C9	117.26 (10)
C12—N3—C4	113.04 (8)	O1—C10—C5	122.45 (10)
N3—C4—C5	111.94 (9)	C9—C10—C5	120.28 (11)
N3—C4—H4A	109.2	C7—C11—H11A	109.5
C5—C4—H4A	109.2	C7—C11—H11B	109.5
N3—C4—H4B	109.2	H11A—C11—H11B	109.5
C5—C4—H4B	109.2	C7—C11—H11C	109.5
H4A—C4—H4B	107.9	H11A—C11—H11C	109.5
C6—C5—C10	118.56 (10)	H11B—C11—H11C	109.5
C6—C5—C4	122.21 (10)	N3—C12—C12i	110.89 (11)
C10—C5—C4	119.22 (10)	N3—C12—H12A	109.5
C7—C6—C5	122.18 (11)	C12i—C12—H12A	109.5
C7—C6—H6	118.9	N3—C12—H12B	109.5
C5—C6—H6	118.9	C12i—C12—H12B	109.5
C6—C7—C8	117.77 (10)	H12A—C12—H12B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ii	0.97	2.57	3.425 (1)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.97	2.57	3.425 (1)	147

Symmetry code: (i) .