N-[4-(β-d-Allopyranos-yloxy)benzyl-idene]methyl-amine.

The title compound, C(14)H(19)NO(6), was synthesized by the condensation reaction between hecilid (4-formyl-phenl-β-d-allopyran-oside) and methyl-amine in methanol. In the crystal structure, the pyran ring adopts a chair conformation and adjacent mol-ecules are linked by inter-molecular O-H⋯O and O-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the pharmaceutical and biological properties of hecilid and its derivatives, see: Chen et al. (1981 ▶); Sha & Mao (1987 ▶); Zhu et al. (2006 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C14H19NO6

M = 297.30

Monoclinic,

a = 6.721 (4) Å

b = 7.751 (3) Å

c = 14.119 (4) Å

β = 91.46 (3)°

V = 735.3 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 292 (2) K

0.48 × 0.46 × 0.44 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

1479 measured reflections

1469 independent reflections

1325 reflections with I > 2σ(I)

R int = 0.004

3 standard reflections every 120 reflections intensity decay: 0.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.09

1469 reflections

195 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000944/rz2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000944/rz2284Isup2.hkl

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

C14H19NO6	F(000) = 316
Mr = 297.30	Dx = 1.343 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.721 (4) Å	θ = 4.2–7.5°
b = 7.751 (3) Å	µ = 0.11 mm−1
c = 14.119 (4) Å	T = 292 K
β = 91.46 (3)°	Block, colourless
V = 735.3 (6) Å3	0.48 × 0.46 × 0.44 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.004
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 1.4°
graphite	h = −8→8
ω/2θ scans	k = 0→9
1479 measured reflections	l = −5→17
1469 independent reflections	3 standard reflections every 120 reflections
1325 reflections with I > 2σ(I)	intensity decay: 0.8%

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.0722P] where P = (Fo2 + 2Fc2)/3
1469 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.24 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 > 2σ(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
O1	0.3071 (3)	−0.0753 (2)	0.21216 (11)	0.0379 (4)
O2	0.4392 (3)	−0.3849 (2)	0.12078 (13)	0.0451 (5)
H2O	0.4074	−0.4260	0.1717	0.068*
O3	0.1787 (3)	0.0239 (3)	−0.03679 (11)	0.0441 (4)
H3O	0.2854	0.0646	−0.0527	0.066*
O4	0.3774 (3)	0.2704 (2)	0.06228 (14)	0.0465 (5)
H4O	0.3892	0.3747	0.0704	0.070*
O5	0.2525 (3)	0.3895 (2)	0.23888 (12)	0.0403 (4)
H5O	0.1701	0.4234	0.2764	0.060*
O6	0.3519 (2)	0.0903 (3)	0.34359 (10)	0.0394 (4)
N1	1.0551 (3)	−0.0235 (3)	0.64875 (15)	0.0434 (5)
C1	0.3201 (4)	−0.0893 (3)	0.11071 (17)	0.0331 (5)
H1	0.4538	−0.0559	0.0915	0.040*
C2	0.1662 (4)	0.0309 (3)	0.06374 (16)	0.0364 (5)
H2	0.0333	−0.0081	0.0811	0.044*
C3	0.1951 (4)	0.2142 (3)	0.09971 (16)	0.0377 (5)
H3	0.0864	0.2873	0.0754	0.045*
C4	0.2018 (4)	0.2204 (3)	0.20805 (16)	0.0336 (5)
H4	0.0711	0.1891	0.2320	0.040*
C5	0.3562 (4)	0.0917 (3)	0.24383 (15)	0.0336 (5)
H5	0.4888	0.1242	0.2227	0.040*
C6	0.2829 (4)	−0.2759 (3)	0.0851 (2)	0.0419 (6)
H6A	0.1575	−0.3126	0.1110	0.050*
H6B	0.2727	−0.2870	0.0167	0.050*
C7	0.5264 (3)	0.0507 (4)	0.39210 (15)	0.0346 (5)
C8	0.5361 (4)	0.1100 (4)	0.48498 (15)	0.0373 (6)
H8	0.4298	0.1704	0.5098	0.045*
C9	0.7042 (4)	0.0788 (4)	0.54001 (15)	0.0380 (6)
H9	0.7102	0.1165	0.6026	0.046*
C10	0.8654 (4)	−0.0086 (3)	0.50277 (16)	0.0372 (6)
C11	0.8541 (4)	−0.0656 (4)	0.40913 (17)	0.0414 (6)
H11	0.9618	−0.1226	0.3834	0.050*
C12	0.6830 (4)	−0.0379 (4)	0.35401 (16)	0.0408 (6)
H12	0.6742	−0.0788	0.2921	0.049*
C13	1.0481 (4)	−0.0398 (4)	0.55985 (18)	0.0415 (6)
H13	1.1629	−0.0727	0.5292	0.050*
C14	1.2474 (4)	−0.0454 (5)	0.6982 (2)	0.0536 (7)
H14A	1.3461	−0.0776	0.6535	0.080*
H14B	1.2368	−0.1341	0.7453	0.080*
H14C	1.2855	0.0611	0.7282	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0468 (9)	0.0314 (9)	0.0350 (9)	−0.0009 (8)	−0.0059 (7)	0.0028 (8)
O2	0.0549 (11)	0.0277 (9)	0.0526 (10)	0.0046 (8)	0.0014 (8)	0.0060 (8)
O3	0.0518 (11)	0.0434 (11)	0.0366 (8)	0.0007 (9)	−0.0127 (7)	−0.0042 (8)
O4	0.0700 (13)	0.0285 (9)	0.0416 (9)	−0.0075 (9)	0.0098 (8)	−0.0041 (8)
O5	0.0488 (11)	0.0329 (9)	0.0394 (9)	−0.0012 (8)	0.0074 (8)	−0.0061 (8)
O6	0.0371 (9)	0.0501 (11)	0.0307 (8)	0.0036 (8)	−0.0039 (7)	0.0020 (8)
N1	0.0370 (11)	0.0493 (14)	0.0435 (11)	−0.0017 (10)	−0.0059 (9)	0.0079 (10)
C1	0.0350 (12)	0.0281 (12)	0.0359 (11)	−0.0010 (10)	−0.0048 (9)	−0.0006 (10)
C2	0.0373 (13)	0.0342 (13)	0.0373 (12)	0.0019 (11)	−0.0098 (10)	−0.0010 (11)
C3	0.0453 (13)	0.0328 (12)	0.0347 (12)	0.0072 (12)	−0.0069 (10)	0.0012 (11)
C4	0.0365 (12)	0.0307 (12)	0.0335 (11)	0.0018 (11)	−0.0007 (9)	−0.0006 (10)
C5	0.0348 (12)	0.0368 (13)	0.0292 (11)	−0.0011 (11)	−0.0017 (9)	0.0012 (10)
C6	0.0464 (14)	0.0284 (13)	0.0504 (14)	−0.0019 (12)	−0.0091 (11)	−0.0016 (11)
C7	0.0364 (12)	0.0338 (12)	0.0334 (11)	−0.0003 (11)	−0.0033 (9)	0.0054 (10)
C8	0.0374 (13)	0.0401 (14)	0.0345 (12)	0.0043 (11)	0.0015 (10)	0.0000 (11)
C9	0.0410 (13)	0.0430 (14)	0.0297 (11)	0.0006 (11)	−0.0009 (9)	0.0004 (11)
C10	0.0381 (13)	0.0366 (13)	0.0368 (12)	−0.0006 (10)	−0.0021 (10)	0.0052 (10)
C11	0.0420 (14)	0.0412 (14)	0.0412 (13)	0.0085 (12)	0.0036 (10)	0.0018 (12)
C12	0.0491 (14)	0.0418 (14)	0.0315 (11)	0.0059 (13)	−0.0031 (10)	−0.0031 (11)
C13	0.0359 (13)	0.0411 (15)	0.0475 (14)	0.0003 (11)	−0.0003 (11)	0.0064 (12)
C14	0.0420 (15)	0.0617 (19)	0.0564 (16)	−0.0042 (15)	−0.0165 (12)	0.0100 (15)

O1—C5	1.406 (3)	C4—C5	1.517 (3)
O1—C1	1.441 (3)	C4—H4	0.9800
O2—C6	1.430 (3)	C5—H5	0.9800
O2—H2O	0.8200	C6—H6A	0.9700
O3—C2	1.425 (3)	C6—H6B	0.9700
O3—H3O	0.8200	C7—C12	1.377 (4)
O4—C3	1.415 (3)	C7—C8	1.390 (3)
O4—H4O	0.8200	C8—C9	1.376 (3)
O5—C4	1.420 (3)	C8—H8	0.9300
O5—H5O	0.8200	C9—C10	1.392 (4)
O6—C7	1.378 (3)	C9—H9	0.9300
O6—C5	1.410 (3)	C10—C11	1.394 (3)
N1—C13	1.261 (3)	C10—C13	1.471 (4)
N1—C14	1.463 (3)	C11—C12	1.389 (4)
C1—C6	1.510 (3)	C11—H11	0.9300
C1—C2	1.531 (3)	C12—H12	0.9300
C1—H1	0.9800	C13—H13	0.9300
C2—C3	1.520 (4)	C14—H14A	0.9600
C2—H2	0.9800	C14—H14B	0.9600
C3—C4	1.530 (3)	C14—H14C	0.9600
C3—H3	0.9800
C5—O1—C1	111.46 (17)	O6—C5—H5	110.4
C6—O2—H2O	109.5	C4—C5—H5	110.4
C2—O3—H3O	109.5	O2—C6—C1	111.5 (2)
C3—O4—H4O	109.5	O2—C6—H6A	109.3
C4—O5—H5O	109.5	C1—C6—H6A	109.3
C7—O6—C5	117.35 (18)	O2—C6—H6B	109.3
C13—N1—C14	118.3 (2)	C1—C6—H6B	109.3
O1—C1—C6	107.3 (2)	H6A—C6—H6B	108.0
O1—C1—C2	109.09 (19)	C12—C7—O6	124.5 (2)
C6—C1—C2	111.9 (2)	C12—C7—C8	121.0 (2)
O1—C1—H1	109.5	O6—C7—C8	114.5 (2)
C6—C1—H1	109.5	C9—C8—C7	119.5 (2)
C2—C1—H1	109.5	C9—C8—H8	120.2
O3—C2—C3	111.0 (2)	C7—C8—H8	120.2
O3—C2—C1	110.6 (2)	C8—C9—C10	120.5 (2)
C3—C2—C1	110.17 (18)	C8—C9—H9	119.7
O3—C2—H2	108.3	C10—C9—H9	119.7
C3—C2—H2	108.3	C9—C10—C11	119.2 (2)
C1—C2—H2	108.3	C9—C10—C13	121.3 (2)
O4—C3—C2	105.5 (2)	C11—C10—C13	119.5 (2)
O4—C3—C4	111.1 (2)	C12—C11—C10	120.5 (2)
C2—C3—C4	111.3 (2)	C12—C11—H11	119.8
O4—C3—H3	109.6	C10—C11—H11	119.8
C2—C3—H3	109.6	C7—C12—C11	119.2 (2)
C4—C3—H3	109.6	C7—C12—H12	120.4
O5—C4—C5	110.4 (2)	C11—C12—H12	120.4
O5—C4—C3	109.7 (2)	N1—C13—C10	122.6 (2)
C5—C4—C3	108.34 (19)	N1—C13—H13	118.7
O5—C4—H4	109.5	C10—C13—H13	118.7
C5—C4—H4	109.5	N1—C14—H14A	109.5
C3—C4—H4	109.5	N1—C14—H14B	109.5
O1—C5—O6	107.48 (19)	H14A—C14—H14B	109.5
O1—C5—C4	110.26 (19)	N1—C14—H14C	109.5
O6—C5—C4	107.84 (19)	H14A—C14—H14C	109.5
O1—C5—H5	110.4	H14B—C14—H14C	109.5
C5—O1—C1—C6	175.0 (2)	O5—C4—C5—O6	63.7 (2)
C5—O1—C1—C2	−63.6 (2)	C3—C4—C5—O6	−176.21 (19)
O1—C1—C2—O3	178.37 (19)	O1—C1—C6—O2	−66.7 (3)
C6—C1—C2—O3	−63.1 (3)	C2—C1—C6—O2	173.71 (19)
O1—C1—C2—C3	55.3 (3)	C5—O6—C7—C12	−21.4 (4)
C6—C1—C2—C3	173.8 (2)	C5—O6—C7—C8	157.8 (2)
O3—C2—C3—O4	−53.9 (2)	C12—C7—C8—C9	−0.4 (4)
C1—C2—C3—O4	68.9 (2)	O6—C7—C8—C9	−179.6 (2)
O3—C2—C3—C4	−174.57 (19)	C7—C8—C9—C10	1.2 (4)
C1—C2—C3—C4	−51.7 (3)	C8—C9—C10—C11	−0.5 (4)
O4—C3—C4—O5	55.8 (3)	C8—C9—C10—C13	178.6 (2)
C2—C3—C4—O5	173.1 (2)	C9—C10—C11—C12	−1.0 (4)
O4—C3—C4—C5	−64.8 (3)	C13—C10—C11—C12	179.9 (3)
C2—C3—C4—C5	52.6 (3)	O6—C7—C12—C11	178.0 (3)
C1—O1—C5—O6	−176.31 (17)	C8—C7—C12—C11	−1.1 (4)
C1—O1—C5—C4	66.4 (2)	C10—C11—C12—C7	1.8 (4)
C7—O6—C5—O1	90.4 (2)	C14—N1—C13—C10	−175.7 (3)
C7—O6—C5—C4	−150.8 (2)	C9—C10—C13—N1	15.4 (4)
O5—C4—C5—O1	−179.22 (19)	C11—C10—C13—N1	−165.5 (3)
C3—C4—C5—O1	−59.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O5i	0.82	2.02	2.742 (3)	147
O3—H3O···O2ii	0.82	2.14	2.942 (3)	165
O4—H4O···O2iii	0.82	2.02	2.824 (3)	167
O5—H5O···N1iv	0.82	1.91	2.723 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O5i	0.82	2.02	2.742 (3)	147
O3—H3O⋯O2ii	0.82	2.14	2.942 (3)	165
O4—H4O⋯O2iii	0.82	2.02	2.824 (3)	167
O5—H5O⋯N1iv	0.82	1.91	2.723 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .