3,3'-(Ethane-1,2-diyl)bis(6-meth-oxy-3,4-dihydro-2H-1,3-benzoxazine) mono-hydrate.

The asymmetric unit of the title compound, C(20)H(24)N(2)O(4)·H(2)O, contains one half-organic mol-ecule (an inversion centre generates the other half of the mol-ecule) and a half-mol-ecule of water (the O atom has site symmetry 2). The near planarity of the fused-benzene ring is illustrated by the very small deviations of all the atoms from the plane [largest deviation = 0.0092 (11) Å. The six-membered N,O-containing ring adopts a half-chair conformation. The observed N-CH(2) and CH(2)-O bond lengths can be correlated to the manifestation of an anomeric effect in the N-CH(2)-O unit. In the crystal, the mol-ecules are connected into zigzag chains parallel to [001] through O-H⋯N hydrogen bonds formed between the oxazinic N atom and the solvent water mol-ecule. The chains are consolidated by C-H⋯O inter-actions.

Related literature

For related structures, see: Rivera et al. (2012 ▶, 2011 ▶, 2010 ▶). For the preparation of the title compound, see: Rivera et al. (1989 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H24N2O4·H2O

M = 374.4

Monoclinic,

a = 30.2999 (9) Å

b = 5.2132 (2) Å

c = 11.6058 (4) Å

β = 91.153 (2)°

V = 1832.87 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.80 mm−1

T = 120 K

0.17 × 0.13 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.104, T max = 1

18257 measured reflections

1639 independent reflections

1440 reflections with I > 3σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.094

S = 1.75

1639 reflections

127 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812035519/bx2424sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035519/bx2424Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035519/bx2424Isup3.cml

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

C20H24N2O4·H2O	F(000) = 800
Mr = 374.4	Dx = 1.357 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 10577 reflections
a = 30.2999 (9) Å	θ = 2.9–67.0°
b = 5.2132 (2) Å	µ = 0.80 mm−1
c = 11.6058 (4) Å	T = 120 K
β = 91.153 (2)°	Prism, white
V = 1832.87 (11) Å3	0.17 × 0.13 × 0.13 mm
Z = 4

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1639 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1440 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 2.9°
ω scans	h = −36→36
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
Tmin = 0.104, Tmax = 1	l = −13→13
18257 measured reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
wR(F2) = 0.094	(Δ/σ)max = 0.015
S = 1.75	Δρmax = 0.17 e Å−3
1639 reflections	Δρmin = −0.14 e Å−3
127 parameters	Extinction correction: B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)
0 restraints	Extinction coefficient: 1300 (300)
49 constraints

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
O1	0.90016 (2)	0.11497 (15)	0.06702 (6)	0.0199 (2)
O2	0.80451 (3)	−0.57728 (15)	−0.19811 (7)	0.0218 (3)
O3	0.5	0.0044 (2)	0.25	0.0278 (4)
N1	0.95328 (3)	0.15870 (18)	−0.08373 (7)	0.0175 (3)
C1	0.92150 (3)	0.0638 (2)	−0.17210 (9)	0.0187 (3)
C2	0.98132 (3)	−0.0506 (2)	−0.03816 (9)	0.0185 (3)
C3	0.87593 (3)	−0.0523 (2)	−0.00091 (9)	0.0170 (3)
C4	0.85915 (3)	−0.2627 (2)	−0.18039 (9)	0.0170 (3)
C5	0.88428 (3)	−0.0852 (2)	−0.11834 (9)	0.0164 (3)
C6	0.82677 (3)	−0.4068 (2)	−0.12743 (9)	0.0177 (3)
C7	0.84416 (4)	−0.1983 (2)	0.05238 (9)	0.0198 (3)
C8	0.81931 (4)	−0.3764 (2)	−0.01008 (10)	0.0200 (3)
C9	0.92843 (3)	0.2868 (2)	0.00424 (9)	0.0179 (3)
C10	0.77298 (4)	−0.7400 (2)	−0.14564 (10)	0.0260 (4)
H1c1	0.936552	−0.044083	−0.225599	0.0225*
H2c1	0.909537	0.206326	−0.214813	0.0225*
H1c2	0.993326	−0.145584	−0.101079	0.0222*
H2c2	0.963614	−0.167436	0.005101	0.0222*
H1c4	0.864263	−0.286099	−0.261076	0.0205*
H1c7	0.839223	−0.176396	0.13323	0.0237*
H1c8	0.79727	−0.477366	0.027191	0.024*
H1c9	0.948384	0.371178	0.05716	0.0215*
H2c9	0.910924	0.420868	−0.030257	0.0215*
H1c10	0.76001	−0.851305	−0.20284	0.0312*
H2c10	0.787328	−0.841082	−0.086776	0.0312*
H3c10	0.750337	−0.637226	−0.111909	0.0312*
H1o3	0.4874 (5)	0.112 (3)	0.3020 (13)	0.0334*

	U11	U22	U33	U12	U13	U23
O1	0.0221 (4)	0.0216 (5)	0.0160 (4)	−0.0038 (3)	0.0011 (3)	−0.0019 (3)
O2	0.0213 (4)	0.0237 (5)	0.0205 (4)	−0.0064 (3)	−0.0002 (3)	−0.0021 (3)
O3	0.0369 (7)	0.0197 (7)	0.0274 (6)	0	0.0112 (5)	0
N1	0.0171 (4)	0.0186 (5)	0.0167 (4)	−0.0008 (4)	−0.0019 (3)	−0.0001 (4)
C1	0.0183 (5)	0.0233 (6)	0.0146 (5)	−0.0022 (5)	−0.0014 (4)	0.0015 (4)
C2	0.0173 (5)	0.0175 (6)	0.0208 (6)	0.0007 (4)	−0.0013 (4)	−0.0009 (4)
C3	0.0168 (5)	0.0171 (6)	0.0171 (6)	0.0027 (4)	−0.0018 (4)	−0.0008 (4)
C4	0.0174 (5)	0.0197 (6)	0.0140 (5)	0.0027 (4)	−0.0007 (4)	0.0007 (4)
C5	0.0151 (5)	0.0175 (6)	0.0166 (5)	0.0025 (4)	−0.0010 (4)	0.0034 (4)
C6	0.0161 (5)	0.0173 (6)	0.0196 (6)	0.0017 (4)	−0.0026 (4)	0.0001 (4)
C7	0.0209 (5)	0.0235 (6)	0.0150 (5)	0.0018 (5)	0.0022 (4)	0.0008 (4)
C8	0.0182 (5)	0.0212 (6)	0.0208 (6)	−0.0011 (4)	0.0031 (4)	0.0033 (4)
C9	0.0179 (5)	0.0162 (6)	0.0195 (5)	−0.0004 (4)	−0.0004 (4)	0.0000 (4)
C10	0.0249 (6)	0.0251 (7)	0.0279 (6)	−0.0096 (5)	−0.0007 (5)	0.0007 (5)

O1—C3	1.3776 (13)	C3—C5	1.4016 (15)
O1—C9	1.4463 (13)	C3—C7	1.3827 (15)
O2—C6	1.3765 (13)	C4—C5	1.3902 (15)
O2—C10	1.4234 (15)	C4—C6	1.3890 (15)
O3—H1o3	0.914 (15)	C4—H1c4	0.96
O3—H1o3i	0.914 (15)	C6—C8	1.3941 (15)
N1—C1	1.4780 (13)	C7—C8	1.3903 (16)
N1—C2	1.4743 (14)	C7—H1c7	0.96
N1—C9	1.4445 (14)	C8—H1c8	0.96
C1—C5	1.5143 (15)	C9—H1c9	0.96
C1—H1c1	0.96	C9—H2c9	0.96
C1—H2c1	0.96	C10—H1c10	0.96
C2—C2ii	1.5181 (14)	C10—H2c10	0.96
C2—H1c2	0.96	C10—H3c10	0.96
C2—H2c2	0.96
C3—O1—C9	114.70 (8)	C1—C5—C3	119.23 (9)
C6—O2—C10	117.04 (8)	C1—C5—C4	122.19 (9)
H1o3—O3—H1o3i	104.2 (14)	C3—C5—C4	118.52 (10)
C1—N1—C2	111.35 (9)	O2—C6—C4	115.30 (9)
C1—N1—C9	107.66 (8)	O2—C6—C8	124.65 (10)
C2—N1—C9	113.16 (8)	C4—C6—C8	120.04 (10)
N1—C1—C5	111.48 (8)	C3—C7—C8	120.60 (10)
N1—C1—H1c1	109.47	C3—C7—H1c7	119.7
N1—C1—H2c1	109.47	C8—C7—H1c7	119.7
C5—C1—H1c1	109.47	C6—C8—C7	119.25 (10)
C5—C1—H2c1	109.47	C6—C8—H1c8	120.38
H1c1—C1—H2c1	107.39	C7—C8—H1c8	120.38
N1—C2—C2ii	111.70 (9)	O1—C9—N1	113.10 (9)
N1—C2—H1c2	109.47	O1—C9—H1c9	109.47
N1—C2—H2c2	109.47	O1—C9—H2c9	109.47
C2ii—C2—H1c2	109.47	N1—C9—H1c9	109.47
C2ii—C2—H2c2	109.47	N1—C9—H2c9	109.47
H1c2—C2—H2c2	107.15	H1c9—C9—H2c9	105.58
O1—C3—C5	121.97 (9)	O2—C10—H1c10	109.47
O1—C3—C7	117.40 (9)	O2—C10—H2c10	109.47
C5—C3—C7	120.56 (10)	O2—C10—H3c10	109.47
C5—C4—C6	121.01 (10)	H1c10—C10—H2c10	109.47
C5—C4—H1c4	119.49	H1c10—C10—H3c10	109.47
C6—C4—H1c4	119.5	H2c10—C10—H3c10	109.47

D—H···A	D—H	H···A	D···A	D—H···A
C4—H1c4···O1iii	0.96	2.46	3.2982 (13)	145.91
O3—H1o3···N1iv	0.914 (15)	2.076 (15)	2.9870 (12)	174.8 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H1c4⋯O1i	0.96	2.46	3.2982 (13)	145.91
O3—H1o3⋯N1ii	0.914 (15)	2.076 (15)	2.9870 (12)	174.8 (13)

Symmetry codes: (i) ; (ii) .