6-Acetoxy-methyl-3-[(2-hydr-oxy-3-methoxy-benzyl-idene)amino]-3,4,5,6-tetra-hydro-2H-pyran-2,4,5-triyl triacetate.

The title compound, C(22)H(27)NO(11), was synthesized by the reaction of 4,5-diacet-oxy-6-acetoxy-methyl-3-amino-tetra-hydro-pyran-2-yl acetate and 2-hydr-oxy-3-methoxy-benzalde-hyde in ethanol. The mol-ecule contains two six-membered rings, one of which is in a chair conformation, and an intra-molecular O-H⋯N hydrogen bond is present.

Related literature

For a Schiff base complex, see: Zhang et al. (2003 ▶). For macrocyclic Schiff base compounds, see: Frischmann et al. (2008 ▶); Jiang et al. (2010 ▶). For 5,5′-dimeth­oxy-2,2′-[4,5-dimethyl-o-phenyl­enebis(nitrilo­methyl­idyne)]diphenol, which shows similar hydrogen-bonding to the title compound, see: Kargar et al. (2010 ▶).

Experimental

Crystal data

C22H27NO11

M = 481.45

Orthorhombic,

a = 10.806 (3) Å

b = 11.151 (3) Å

c = 20.243 (5) Å

V = 2439.2 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.32 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

12313 measured reflections

2460 independent reflections

1506 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.126

S = 1.03

2460 reflections

314 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011475/si2250sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011475/si2250Isup2.hkl

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

C22H27NO11	F(000) = 1016
Mr = 481.45	Dx = 1.311 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1384 reflections
a = 10.806 (3) Å	θ = 2.6–18.6°
b = 11.151 (3) Å	µ = 0.11 mm−1
c = 20.243 (5) Å	T = 296 K
V = 2439.2 (11) Å3	Block, colourless
Z = 4	0.32 × 0.28 × 0.22 mm

Bruker SMART CCD area-detector diffractometer	1506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
graphite	θmax = 25.1°, θmin = 2.0°
phi and ω scans	h = −12→12
12313 measured reflections	k = −12→13
2460 independent reflections	l = −24→24

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.177P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2460 reflections	Δρmax = 0.17 e Å−3
314 parameters	Δρmin = −0.14 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: 0.0074 (13)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.4441 (3)	0.0108 (3)	−0.01092 (15)	0.0566 (9)
O1	0.2954 (3)	−0.1155 (2)	−0.08619 (14)	0.0650 (8)
H1	0.3485	−0.1041	−0.0580	0.098*
O2	0.1136 (3)	−0.1188 (3)	−0.17050 (16)	0.0796 (10)
O3	0.5742 (3)	−0.0540 (2)	0.15220 (13)	0.0587 (8)
O4	0.3813 (3)	0.0041 (3)	0.12705 (14)	0.0679 (8)
O5	0.2923 (4)	−0.1724 (4)	0.1455 (2)	0.1216 (16)
O6	0.7049 (3)	0.0885 (2)	−0.01748 (13)	0.0653 (8)
O7	0.7871 (5)	−0.0297 (4)	−0.09480 (18)	0.1221 (16)
O8	0.8528 (3)	−0.1002 (3)	0.05512 (15)	0.0654 (8)
O9	0.9690 (4)	0.0649 (4)	0.0508 (2)	0.1069 (14)
O10	0.8042 (3)	−0.0141 (3)	0.21533 (14)	0.0709 (9)
O11	0.9237 (4)	−0.1041 (4)	0.2885 (2)	0.1134 (15)
C1	0.3183 (4)	0.0980 (4)	−0.09509 (19)	0.0564 (11)
C2	0.2611 (4)	−0.0094 (4)	−0.11268 (17)	0.0523 (10)
C3	0.1641 (4)	−0.0085 (4)	−0.1582 (2)	0.0579 (11)
C4	0.1275 (5)	0.0970 (4)	−0.1868 (2)	0.0686 (13)
H4	0.0620	0.0974	−0.2166	0.082*
C5	0.1877 (6)	0.2026 (4)	−0.1716 (2)	0.0830 (17)
H5	0.1651	0.2735	−0.1925	0.100*
C6	0.2796 (5)	0.2030 (4)	−0.1261 (2)	0.0763 (15)
H6	0.3178	0.2752	−0.1153	0.092*
C7	0.0039 (5)	−0.1240 (5)	−0.2101 (2)	0.0794 (15)
H7A	−0.0601	−0.0770	−0.1898	0.119*
H7B	−0.0230	−0.2057	−0.2139	0.119*
H7C	0.0213	−0.0927	−0.2533	0.119*
C8	0.4107 (4)	0.1028 (4)	−0.0435 (2)	0.0593 (11)
H8	0.4473	0.1762	−0.0338	0.071*
C9	0.4872 (4)	−0.0535 (4)	0.1006 (2)	0.0590 (11)
H9	0.4679	−0.1351	0.0859	0.071*
C10	0.5319 (4)	0.0245 (4)	0.0434 (2)	0.0545 (11)
H10	0.5334	0.1086	0.0575	0.065*
C11	0.6604 (4)	−0.0123 (4)	0.02084 (19)	0.0537 (10)
H11	0.6556	−0.0841	−0.0070	0.064*
C12	0.7471 (4)	−0.0339 (3)	0.07825 (18)	0.0524 (10)
H12	0.7737	0.0427	0.0972	0.063*
C13	0.6865 (4)	−0.1114 (4)	0.13127 (19)	0.0562 (11)
H13	0.6663	−0.1898	0.1123	0.067*
C14	0.2886 (5)	−0.0675 (6)	0.1493 (3)	0.0823 (16)
C15	0.1874 (5)	0.0050 (6)	0.1787 (3)	0.1032 (19)
H15A	0.1311	−0.0468	0.2018	0.155*
H15B	0.1438	0.0466	0.1443	0.155*
H15C	0.2217	0.0622	0.2091	0.155*
C16	0.7680 (6)	0.0677 (5)	−0.0739 (2)	0.0792 (15)
C17	0.8086 (7)	0.1835 (6)	−0.1032 (3)	0.120 (2)
H17A	0.8882	0.1734	−0.1234	0.180*
H17B	0.8140	0.2432	−0.0692	0.180*
H17C	0.7498	0.2086	−0.1359	0.180*
C18	0.9585 (5)	−0.0393 (6)	0.0418 (3)	0.0821 (15)
C19	1.0539 (6)	−0.1225 (6)	0.0159 (3)	0.124 (2)
H19A	1.0194	−0.1692	−0.0194	0.187*
H19B	1.0809	−0.1750	0.0507	0.187*
H19C	1.1231	−0.0773	−0.0003	0.187*
C20	0.7666 (5)	−0.1294 (4)	0.1910 (2)	0.0670 (13)
H20A	0.7209	−0.1721	0.2249	0.080*
H20B	0.8388	−0.1766	0.1794	0.080*
C21	0.8859 (5)	−0.0145 (5)	0.2653 (2)	0.0731 (14)
C22	0.9208 (6)	0.1090 (5)	0.2857 (3)	0.0973 (18)
H22A	0.8510	0.1476	0.3059	0.146*
H22B	0.9463	0.1540	0.2476	0.146*
H22C	0.9878	0.1053	0.3168	0.146*

	U11	U22	U33	U12	U13	U23
N1	0.062 (2)	0.055 (2)	0.0534 (19)	0.0008 (19)	−0.0100 (17)	−0.0002 (18)
O1	0.069 (2)	0.0494 (16)	0.077 (2)	0.0002 (16)	−0.0246 (18)	0.0102 (14)
O2	0.083 (2)	0.061 (2)	0.095 (2)	−0.0107 (18)	−0.037 (2)	0.0081 (17)
O3	0.060 (2)	0.0645 (18)	0.0515 (17)	0.0054 (15)	−0.0011 (16)	0.0003 (13)
O4	0.0571 (19)	0.075 (2)	0.0714 (18)	0.0045 (19)	0.0075 (17)	0.0013 (17)
O5	0.099 (3)	0.096 (3)	0.170 (4)	−0.015 (3)	0.035 (3)	0.016 (3)
O6	0.074 (2)	0.0671 (18)	0.0549 (17)	−0.0070 (17)	−0.0021 (17)	0.0039 (15)
O7	0.175 (5)	0.109 (3)	0.083 (2)	−0.002 (3)	0.043 (3)	−0.015 (2)
O8	0.057 (2)	0.0658 (18)	0.0736 (19)	0.0114 (17)	0.0010 (16)	−0.0063 (16)
O9	0.073 (3)	0.095 (3)	0.153 (4)	−0.014 (2)	0.009 (3)	−0.006 (3)
O10	0.080 (2)	0.0673 (19)	0.0651 (17)	0.0067 (19)	−0.0188 (18)	−0.0055 (15)
O11	0.113 (4)	0.111 (3)	0.116 (3)	0.022 (3)	−0.055 (3)	0.003 (3)
C1	0.067 (3)	0.049 (2)	0.054 (2)	0.004 (2)	−0.008 (2)	0.000 (2)
C2	0.057 (3)	0.050 (2)	0.049 (2)	0.001 (2)	−0.005 (2)	0.0066 (19)
C3	0.062 (3)	0.052 (2)	0.059 (2)	0.002 (2)	−0.011 (2)	0.005 (2)
C4	0.072 (3)	0.064 (3)	0.070 (3)	0.009 (3)	−0.019 (3)	0.003 (2)
C5	0.107 (5)	0.051 (3)	0.091 (3)	0.006 (3)	−0.042 (4)	0.013 (2)
C6	0.094 (4)	0.047 (2)	0.088 (3)	−0.004 (3)	−0.030 (3)	−0.001 (2)
C7	0.073 (4)	0.079 (3)	0.085 (3)	−0.017 (3)	−0.026 (3)	0.014 (3)
C8	0.060 (3)	0.054 (2)	0.064 (3)	−0.002 (2)	−0.004 (2)	−0.005 (2)
C9	0.054 (3)	0.066 (3)	0.057 (3)	0.004 (2)	−0.002 (2)	−0.001 (2)
C10	0.056 (3)	0.051 (2)	0.057 (2)	−0.003 (2)	−0.007 (2)	−0.004 (2)
C11	0.059 (3)	0.047 (2)	0.055 (2)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C12	0.054 (3)	0.050 (2)	0.053 (2)	0.007 (2)	−0.001 (2)	−0.0019 (18)
C13	0.062 (3)	0.053 (2)	0.054 (2)	0.002 (2)	−0.006 (2)	−0.002 (2)
C14	0.062 (4)	0.103 (4)	0.082 (3)	0.000 (3)	0.007 (3)	0.019 (3)
C15	0.051 (3)	0.151 (5)	0.108 (4)	0.009 (4)	0.012 (3)	0.021 (4)
C16	0.088 (4)	0.092 (4)	0.058 (3)	−0.012 (3)	0.000 (3)	0.003 (3)
C17	0.147 (7)	0.131 (5)	0.083 (4)	−0.049 (5)	0.010 (4)	0.017 (4)
C18	0.060 (4)	0.101 (4)	0.086 (4)	0.012 (3)	0.007 (3)	0.004 (3)
C19	0.083 (4)	0.158 (6)	0.132 (5)	0.035 (5)	0.023 (4)	−0.031 (5)
C20	0.072 (3)	0.063 (3)	0.066 (3)	0.006 (3)	−0.009 (3)	0.000 (2)
C21	0.067 (3)	0.088 (4)	0.064 (3)	0.006 (3)	−0.013 (3)	−0.006 (3)
C22	0.079 (4)	0.119 (5)	0.094 (4)	−0.002 (4)	−0.017 (3)	−0.028 (4)

N1—C8	1.271 (5)	C7—H7B	0.9600
N1—C10	1.461 (5)	C7—H7C	0.9600
O1—C2	1.351 (4)	C8—H8	0.9300
O1—H1	0.8200	C9—C10	1.526 (6)
O2—C3	1.368 (5)	C9—H9	0.9800
O2—C7	1.433 (5)	C10—C11	1.519 (6)
O3—C9	1.406 (5)	C10—H10	0.9800
O3—C13	1.435 (5)	C11—C12	1.512 (5)
O4—C14	1.359 (6)	C11—H11	0.9800
O4—C9	1.417 (5)	C12—C13	1.525 (6)
O5—C14	1.172 (6)	C12—H12	0.9800
O6—C16	1.350 (6)	C13—C20	1.501 (6)
O6—C11	1.448 (5)	C13—H13	0.9800
O7—C16	1.184 (6)	C14—C15	1.485 (7)
O8—C18	1.356 (6)	C15—H15A	0.9600
O8—C12	1.438 (5)	C15—H15B	0.9600
O9—C18	1.182 (6)	C15—H15C	0.9600
O10—C21	1.343 (5)	C16—C17	1.486 (7)
O10—C20	1.435 (5)	C17—H17A	0.9600
O11—C21	1.176 (5)	C17—H17B	0.9600
C1—C6	1.393 (6)	C17—H17C	0.9600
C1—C2	1.394 (5)	C18—C19	1.483 (7)
C1—C8	1.446 (6)	C19—H19A	0.9600
C2—C3	1.395 (5)	C19—H19B	0.9600
C3—C4	1.370 (6)	C19—H19C	0.9600
C4—C5	1.380 (6)	C20—H20A	0.9700
C4—H4	0.9300	C20—H20B	0.9700
C5—C6	1.354 (6)	C21—C22	1.487 (7)
C5—H5	0.9300	C22—H22A	0.9600
C6—H6	0.9300	C22—H22B	0.9600
C7—H7A	0.9600	C22—H22C	0.9600
C8—N1—C10	119.4 (3)	O8—C12—C13	106.2 (3)
C2—O1—H1	109.5	C11—C12—C13	111.4 (3)
C3—O2—C7	117.9 (3)	O8—C12—H12	110.1
C9—O3—C13	110.4 (3)	C11—C12—H12	110.1
C14—O4—C9	117.0 (4)	C13—C12—H12	110.1
C16—O6—C11	119.2 (4)	O3—C13—C20	108.0 (3)
C18—O8—C12	118.5 (3)	O3—C13—C12	108.6 (3)
C21—O10—C20	116.2 (4)	C20—C13—C12	113.3 (4)
C6—C1—C2	118.3 (4)	O3—C13—H13	109.0
C6—C1—C8	120.2 (4)	C20—C13—H13	109.0
C2—C1—C8	121.5 (4)	C12—C13—H13	109.0
O1—C2—C1	122.0 (3)	O5—C14—O4	122.6 (6)
O1—C2—C3	118.3 (4)	O5—C14—C15	126.5 (6)
C1—C2—C3	119.7 (4)	O4—C14—C15	110.8 (5)
O2—C3—C4	125.4 (4)	C14—C15—H15A	109.5
O2—C3—C2	114.4 (3)	C14—C15—H15B	109.5
C4—C3—C2	120.2 (4)	H15A—C15—H15B	109.5
C3—C4—C5	120.1 (4)	C14—C15—H15C	109.5
C3—C4—H4	120.0	H15A—C15—H15C	109.5
C5—C4—H4	120.0	H15B—C15—H15C	109.5
C6—C5—C4	120.1 (4)	O7—C16—O6	123.2 (5)
C6—C5—H5	120.0	O7—C16—C17	127.0 (5)
C4—C5—H5	120.0	O6—C16—C17	109.7 (5)
C5—C6—C1	121.6 (4)	C16—C17—H17A	109.5
C5—C6—H6	119.2	C16—C17—H17B	109.5
C1—C6—H6	119.2	H17A—C17—H17B	109.5
O2—C7—H7A	109.5	C16—C17—H17C	109.5
O2—C7—H7B	109.5	H17A—C17—H17C	109.5
H7A—C7—H7B	109.5	H17B—C17—H17C	109.5
O2—C7—H7C	109.5	O9—C18—O8	122.9 (5)
H7A—C7—H7C	109.5	O9—C18—C19	127.1 (6)
H7B—C7—H7C	109.5	O8—C18—C19	110.0 (5)
N1—C8—C1	122.8 (4)	C18—C19—H19A	109.5
N1—C8—H8	118.6	C18—C19—H19B	109.5
C1—C8—H8	118.6	H19A—C19—H19B	109.5
O3—C9—O4	105.2 (3)	C18—C19—H19C	109.5
O3—C9—C10	110.7 (3)	H19A—C19—H19C	109.5
O4—C9—C10	106.5 (3)	H19B—C19—H19C	109.5
O3—C9—H9	111.4	O10—C20—C13	108.6 (3)
O4—C9—H9	111.4	O10—C20—H20A	110.0
C10—C9—H9	111.4	C13—C20—H20A	110.0
N1—C10—C11	109.8 (3)	O10—C20—H20B	110.0
N1—C10—C9	107.9 (3)	C13—C20—H20B	110.0
C11—C10—C9	111.4 (3)	H20A—C20—H20B	108.3
N1—C10—H10	109.3	O11—C21—O10	122.1 (5)
C11—C10—H10	109.3	O11—C21—C22	126.0 (5)
C9—C10—H10	109.3	O10—C21—C22	111.9 (5)
O6—C11—C12	109.3 (3)	C21—C22—H22A	109.5
O6—C11—C10	104.8 (3)	C21—C22—H22B	109.5
C12—C11—C10	112.2 (3)	H22A—C22—H22B	109.5
O6—C11—H11	110.1	C21—C22—H22C	109.5
C12—C11—H11	110.1	H22A—C22—H22C	109.5
C10—C11—H11	110.1	H22B—C22—H22C	109.5
O8—C12—C11	108.9 (3)
C6—C1—C2—O1	178.2 (4)	C16—O6—C11—C12	100.4 (4)
C8—C1—C2—O1	−5.2 (6)	C16—O6—C11—C10	−139.2 (4)
C6—C1—C2—C3	−2.7 (6)	N1—C10—C11—O6	77.7 (4)
C8—C1—C2—C3	173.9 (4)	C9—C10—C11—O6	−162.9 (3)
C7—O2—C3—C4	−8.2 (7)	N1—C10—C11—C12	−163.8 (3)
C7—O2—C3—C2	172.3 (4)	C9—C10—C11—C12	−44.4 (4)
O1—C2—C3—O2	0.3 (6)	C18—O8—C12—C11	99.4 (4)
C1—C2—C3—O2	−178.7 (4)	C18—O8—C12—C13	−140.6 (4)
O1—C2—C3—C4	−179.1 (4)	O6—C11—C12—O8	−80.6 (4)
C1—C2—C3—C4	1.8 (6)	C10—C11—C12—O8	163.6 (3)
O2—C3—C4—C5	−178.4 (5)	O6—C11—C12—C13	162.6 (3)
C2—C3—C4—C5	1.0 (7)	C10—C11—C12—C13	46.8 (4)
C3—C4—C5—C6	−2.8 (8)	C9—O3—C13—C20	−169.9 (3)
C4—C5—C6—C1	1.8 (8)	C9—O3—C13—C12	66.9 (4)
C2—C1—C6—C5	0.9 (7)	O8—C12—C13—O3	−175.1 (3)
C8—C1—C6—C5	−175.7 (5)	C11—C12—C13—O3	−56.7 (4)
C10—N1—C8—C1	−175.9 (4)	O8—C12—C13—C20	64.9 (4)
C6—C1—C8—N1	175.8 (4)	C11—C12—C13—C20	−176.7 (3)
C2—C1—C8—N1	−0.8 (7)	C9—O4—C14—O5	−2.3 (8)
C13—O3—C9—O4	179.7 (3)	C9—O4—C14—C15	176.9 (4)
C13—O3—C9—C10	−65.7 (4)	C11—O6—C16—O7	1.7 (8)
C14—O4—C9—O3	−98.4 (4)	C11—O6—C16—C17	−177.7 (4)
C14—O4—C9—C10	144.0 (4)	C12—O8—C18—O9	3.0 (8)
C8—N1—C10—C11	−100.9 (4)	C12—O8—C18—C19	−177.5 (4)
C8—N1—C10—C9	137.6 (4)	C21—O10—C20—C13	−174.1 (4)
O3—C9—C10—N1	174.0 (3)	O3—C13—C20—O10	−66.5 (4)
O4—C9—C10—N1	−72.1 (4)	C12—C13—C20—O10	53.8 (5)
O3—C9—C10—C11	53.4 (4)	C20—O10—C21—O11	−0.8 (7)
O4—C9—C10—C11	167.3 (3)	C20—O10—C21—C22	178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.625 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.625 (4)	147