3,3'-Ethyl-enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine).

The asymmetric unit of the title compound, C(18)H(18)Cl(2)N(2)O(2), contains one half of an independent mol-ecule, the other half being generated via a centre of inversion at the mol-ecular centroid. In the crystal structure, mol-ecular chains are formed through non-classical C-H⋯ O hydrogen bonds between an axial H atom of the oxazine ring and the O atom of a neighbouring mol-ecule.

Related literature

For the synthesis, see: Rivera et al. (1989 ▶). For related structures, see: Rivera et al. (1986 ▶); Huerta et al. (2006 ▶); Chen & Wu (2007 ▶); Ranjith et al. (2009 ▶). 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

C18H18Cl2N2O2

M = 365.3

Monoclinic,

a = 18.9920 (5) Å

b = 5.8884 (2) Å

c = 17.8813 (5) Å

β = 125.449 (4)°

V = 1629.03 (12) Å3

Z = 4

Cu Kα radiation

μ = 3.70 mm−1

T = 120 K

0.30 × 0.19 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.593, T max = 0.787

12716 measured reflections

1442 independent reflections

1344 reflections with I > 3σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.103

S = 2.26

1442 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014248/fj2292sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014248/fj2292Isup2.hkl

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

C18H18Cl2N2O2	F(000) = 760
Mr = 365.3	Dx = 1.489 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 10117 reflections
a = 18.9920 (5) Å	θ = 3.0–66.8°
b = 5.8884 (2) Å	µ = 3.70 mm−1
c = 17.8813 (5) Å	T = 120 K
β = 125.449 (4)°	Prism, colorless
V = 1629.03 (12) Å3	0.30 × 0.19 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1442 independent reflections
Radiation source: X-ray tube	1344 reflections with I > 3σ(I)
mirror	Rint = 0.024
Detector resolution: 10.3784 pixels mm-1	θmax = 75.1°, θmin = 5.4°
Rotation method data acquisition using ω scans	h = −22→22
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −7→6
Tmin = 0.593, Tmax = 0.787	l = −19→20
12716 measured reflections

Refinement on F2	36 constraints
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.103	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 2.26	(Δ/σ)max = 0.014
1442 reflections	Δρmax = 0.25 e Å−3
109 parameters	Δρmin = −0.25 e Å−3
0 restraints

Experimental. CrysAlisPro (Oxford Diffraction Ltd., Version 1.171.33.51 (release 27-10-2009 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
Cl1	0.60192 (2)	−0.00670 (6)	0.93208 (3)	0.0280 (3)
O1	0.67792 (6)	0.65142 (16)	0.72490 (7)	0.0215 (5)
N1	0.60904 (7)	0.4270 (2)	0.58616 (8)	0.0180 (5)
C1	0.53100 (8)	0.5511 (3)	0.54598 (10)	0.0185 (7)
C2	0.67854 (8)	0.5625 (3)	0.64492 (10)	0.0198 (6)
C3	0.65998 (9)	0.4905 (2)	0.77097 (11)	0.0192 (7)
C4	0.62512 (8)	0.2799 (2)	0.73128 (10)	0.0190 (6)
C5	0.61011 (8)	0.2223 (2)	0.63683 (10)	0.0191 (6)
C6	0.60690 (8)	0.1294 (2)	0.78148 (10)	0.0208 (6)
C7	0.62347 (9)	0.1873 (3)	0.86889 (10)	0.0233 (7)
C8	0.65769 (9)	0.3956 (3)	0.90753 (11)	0.0261 (7)
C9	0.67601 (10)	0.5459 (3)	0.85788 (11)	0.0246 (7)
H1a	0.54087	0.707097	0.539047	0.0222*
H1b	0.509368	0.533303	0.582633	0.0222*
H2a	0.679796	0.688363	0.61157	0.0238*
H2b	0.730991	0.479648	0.668433	0.0238*
H5a	0.65391	0.118579	0.647102	0.023*
H5b	0.556851	0.140341	0.598522	0.023*
H6	0.582529	−0.016899	0.755597	0.0249*
H8	0.668857	0.438584	0.965284	0.0313*
H9	0.700365	0.691858	0.884131	0.0295*

	U11	U22	U33	U12	U13	U23
Cl1	0.0306 (3)	0.0293 (3)	0.0288 (3)	0.00199 (13)	0.0199 (2)	0.00560 (14)
O1	0.0192 (5)	0.0205 (6)	0.0179 (5)	−0.0041 (4)	0.0068 (4)	−0.0012 (4)
N1	0.0124 (5)	0.0177 (6)	0.0169 (6)	0.0007 (4)	0.0044 (5)	0.0005 (5)
C1	0.0141 (6)	0.0178 (7)	0.0161 (8)	0.0023 (5)	0.0045 (6)	0.0013 (6)
C2	0.0150 (6)	0.0227 (7)	0.0174 (7)	−0.0018 (5)	0.0069 (6)	−0.0001 (6)
C3	0.0137 (6)	0.0193 (8)	0.0183 (8)	0.0015 (4)	0.0057 (6)	0.0018 (5)
C4	0.0131 (6)	0.0203 (7)	0.0172 (7)	0.0028 (5)	0.0052 (5)	0.0006 (5)
C5	0.0162 (6)	0.0173 (7)	0.0176 (7)	0.0010 (5)	0.0062 (5)	0.0011 (5)
C6	0.0146 (6)	0.0193 (7)	0.0231 (8)	0.0016 (5)	0.0079 (6)	0.0007 (6)
C7	0.0194 (6)	0.0251 (8)	0.0248 (8)	0.0042 (5)	0.0125 (6)	0.0053 (6)
C8	0.0267 (7)	0.0282 (8)	0.0210 (8)	0.0026 (6)	0.0125 (6)	−0.0014 (6)
C9	0.0233 (7)	0.0217 (7)	0.0228 (8)	−0.0005 (6)	0.0100 (6)	−0.0023 (6)

Cl1—C7	1.813 (2)	C3—C9	1.437 (3)
O1—C2	1.529 (2)	C4—C5	1.578 (3)
O1—C3	1.421 (2)	C4—C6	1.439 (3)
N1—C1	1.4182 (18)	C5—H5a	0.96
N1—C2	1.3690 (16)	C5—H5b	0.96
N1—C5	1.501 (2)	C6—C7	1.445 (3)
C1—C1i	1.4853 (18)	C6—H6	0.96
C1—H1a	0.96	C7—C8	1.372 (2)
C1—H1b	0.96	C8—C9	1.432 (3)
C2—H2a	0.96	C8—H8	0.96
C2—H2b	0.96	C9—H9	0.96
C3—C4	1.3907 (19)
C2—O1—C3	116.65 (11)	C3—C4—C6	116.51 (16)
C1—N1—C2	110.35 (12)	C5—C4—C6	125.13 (12)
C1—N1—C5	111.32 (14)	N1—C5—C4	113.84 (12)
C2—N1—C5	109.60 (10)	N1—C5—H5a	109.4703
N1—C1—C1i	106.07 (13)	N1—C5—H5b	109.4713
N1—C1—H1a	109.4706	C4—C5—H5a	109.4721
N1—C1—H1b	109.4717	C4—C5—H5b	109.4707
C1i—C1—H1a	109.47	H5a—C5—H5b	104.7188
C1i—C1—H1b	109.4723	C4—C6—C7	123.28 (13)
H1a—C1—H1b	112.6688	C4—C6—H6	118.3591
O1—C2—N1	112.97 (15)	C7—C6—H6	118.3615
O1—C2—H2a	109.4708	Cl1—C7—C6	122.62 (11)
O1—C2—H2b	109.4711	Cl1—C7—C8	117.49 (15)
N1—C2—H2a	109.471	C6—C7—C8	119.88 (18)
N1—C2—H2b	109.4715	C7—C8—C9	117.04 (18)
H2a—C2—H2b	105.7297	C7—C8—H8	121.4818
O1—C3—C4	120.14 (17)	C9—C8—H8	121.4814
O1—C3—C9	120.27 (12)	C3—C9—C8	123.70 (14)
C4—C3—C9	119.58 (17)	C3—C9—H9	118.1485
C3—C4—C5	118.35 (16)	C8—C9—H9	118.1475
C2—N1—C1—C1i	150.21 (14)	C9—C3—C4—C6	0.2 (3)
C5—N1—C1—C1i	−87.87 (15)	O1—C3—C9—C8	178.38 (17)
C3—O1—C2—N1	46.41 (18)	C4—C3—C9—C8	−0.3 (3)
C2—O1—C3—C4	−14.6 (2)	C3—C4—C5—N1	−18.4 (2)
C2—O1—C3—C9	166.66 (16)	C6—C4—C5—N1	162.77 (15)
C1—N1—C2—O1	61.58 (16)	C3—C4—C6—C7	−0.3 (3)
C5—N1—C2—O1	−61.37 (17)	C5—C4—C6—C7	178.57 (16)
C1—N1—C5—C4	−74.43 (16)	C4—C6—C7—Cl1	−178.83 (13)
C2—N1—C5—C4	47.92 (19)	C4—C6—C7—C8	0.5 (3)
N1—C1—C1i—N1i	180.00 (13)	Cl1—C7—C8—C9	178.84 (14)
O1—C3—C4—C5	2.6 (2)	C6—C7—C8—C9	−0.5 (3)
O1—C3—C4—C6	−178.46 (15)	C7—C8—C9—C3	0.5 (3)
C9—C3—C4—C5	−178.74 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1ii	0.96	2.56	3.369 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.96	2.56	3.369 (2)	142

Symmetry code: (i) .