N-[4-(β-d-Allopyranos­yloxy)benzyl­idene]methyl­amine

Lv, S.-M.; Zheng, L.; Zhao, H.; Li, Y.; Yin, S.-F.

doi:10.1107/S1600536809000944

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o290

doi:10.1107/S1600536809000944

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N-[4-(β-D-Allopyranosyloxy)benzylidene]methylamine

Shi-Ming Lv,^a Lei Zheng,^a Hui Zhao,^a Ying Li ^a and Shu-Fan Yin ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: chuandayouji217@163.com

(Received 23 December 2008; accepted 8 January 2009; online 10 January 2009)

The title compound, C₁₄H₁₉NO₆, was synthesized by the condensation reaction between hecilid (4-formylphenl-β-D-allopyranoside) and methylamine in methanol. In the crystal structure, the pyran ring adopts a chair conformation and adjacent molecules are linked by intermolecular 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_r = 297.30
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.09
1469 reflections
195 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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⋯N1^iv	0.82	1.91	2.723 (3)	170
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) x, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

The natural compound hecilid (systematic name: 4-formylphenl-β-D-allopyranoside], which is extracted from the fruit of Helicia nilagirica Beed. (Chen et al., 1981), has been one major active ingredient of herb medicine used in China for a long time. It has manifested good biological effects on the central nervous system and a low toxicity (Sha & Mao, 1987). Some derivatives of this compound have been reported with good pharmacological activities (Zhu et al., 2006; Yang et al., 2008). The title compound, a new helicid-derived compound, was synthesized via condensation reaction of hecilid and methyl amine with good yield.

In the molecule of the title compound (Fig. 1), the average of C–C bond length in the hexatomic ring is 1.524 (3) Å; The average C(sp³)–O and C(sp²)–O bond lengths are 1.421 (3) and 1.378 (3) Å, respectively. The hexatomic ring adopts chair conformation with the hydroxy group at C3 in axial position and the other substituents at C1, C2 and C4 in equatorial positions. The C(14)–N(1)–C(13)–C(10) and C(11)–C(10)–C(13)–N(1) torsion angles are -175.7 (3) and -165.5 (3) °, respectively, possibly as a consequence of O—H···.N hydrogen bond. In the crystal packing, intermolecular O—H···.O and O—H···.N hydrogen bonds (Table 1) link the molecules into a three-dimensional network.

Related literature top

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 top

A solution of helicid (1.42 g, 5 mmol) in methanol (8 ml) and a 40% aqueous solution of methyl amine (0.75 ml, 10 mmol) was subjected to ultrasonic radiation for 3 h at 333 K. On cooling to room temperature, colourless crystals were obtained unintentionally.

Computing details top

Data collection: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC (Gabe et al., 1993); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

N-[4-(β-D-Allopyranosyloxy)benzylidene]methylamine top

Crystal data top

C₁₄H₁₉NO₆	F(000) = 316
M_r = 297.30	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.004
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.4°
Graphite monochromator	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 top

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(F_o²) + (0.0607P)² + 0.0722P] where P = (F_o² + 2F_c²)/3
1469 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₉NO₆	V = 735.3 (6) Å³
M_r = 297.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.721 (4) Å	µ = 0.11 mm⁻¹
b = 7.751 (3) Å	T = 292 K
c = 14.119 (4) Å	0.48 × 0.46 × 0.44 mm
β = 91.46 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.004
1479 measured reflections	3 standard reflections every 120 reflections
1469 independent reflections	intensity decay: 0.8%
1325 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.093	H-atom parameters constrained
S = 1.09	Δρ_max = 0.16 e Å⁻³
1469 reflections	Δρ_min = −0.25 e Å⁻³
195 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···N1^iv	0.82	1.91	2.723 (3)	170

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉NO₆
M_r	297.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	6.721 (4), 7.751 (3), 14.119 (4)
β (°)	91.46 (3)
V (Å³)	735.3 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.48 × 0.46 × 0.44

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1479, 1469, 1325
R_int	0.004
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.09
No. of reflections	1469
No. of parameters	195
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: DIFRAC (Gabe et al., 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O5ⁱ	0.82	2.02	2.742 (3)	146.7
O3—H3O···O2ⁱⁱ	0.82	2.14	2.942 (3)	164.7
O4—H4O···O2ⁱⁱⁱ	0.82	2.02	2.824 (3)	166.7
O5—H5O···N1^iv	0.82	1.91	2.723 (3)	169.6

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

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