5-[(3,4-Dimethoxy­benzyl)­aminomethyl­ene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Li, R.; Shi, J.-Y.; Ding, Z.-Y.; Wei, Y.-Q.; Ding, J.

doi:10.1107/S1600536809017413

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1298-o1299

doi:10.1107/S1600536809017413

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5-[(3,4-Dimethoxybenzyl)aminomethylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Rui Li,^a ^* Jian-You Shi,^b Zhen-Yu Ding,^a Yu-Quan Wei ^a and Jian Ding ^c

^aState Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, People's Republic of China, ^bDepartment of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, and ^cState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
^*Correspondence e-mail: lirui@scu.edu.cn

(Received 29 April 2009; accepted 8 May 2009; online 14 May 2009)

The title compound, C₁₅H₁₇NO₆, is approximately planar, with dihedral angles of 3.11 (4) and 2.12 (4)° between the connecting aminomethylene unit and the planar part of the dioxane ring, and between the dimethoxybenzyl ring and the aminomethylene group, respectively. The dioxane ring exhibits a half-boat conformation, in which the C atom between the dioxane O atoms is 0.5471 (8) Å out of the plane. The molecule has an intramolecular N—H⋯O hydrogen bond which may stabilize the planar conformation. In the crystal, weak intermolecular C—H⋯O hydrogen-bonding contacts, result in the formation of sheets parallel to the ab plane.

Related literature

For the synthesis of related compounds, see: Cassis et al. (1985 ). For the synthesis of related antitumor precursors, see Ruchelman et al. (2003 ). For the structure of 5-(aminomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, see: da Silva et al. (2006 ). For Meldrum's acid, see: Meldrum (1908 ).

Experimental

Crystal data

C₁₅H₁₇NO₆
M_r = 307.30
Monoclinic, P 2₁ /c
a = 6.270 (4) Å
b = 12.486 (4) Å
c = 19.529 (5) Å
β = 106.31 (3)°
V = 1467.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 292 K
0.44 × 0.38 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2852 measured reflections
2657 independent reflections
1675 reflections with I > 2σ(I)
R_int = 0.008
3 standard reflections every 150 reflections intensity decay: 1.8%

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.160
S = 1.03
2657 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.86 (3)	2.11 (3)	2.744 (3)	130 (2)
C9—H9⋯O4ⁱ	0.93	2.40	3.309 (4)	164
C15—H15C⋯O3ⁱⁱ	0.96	2.59	3.528 (4)	166
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: DIFRAC (Gabe & White, 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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017413/si2171sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017413/si2171Isup2.hkl

checkCIF report

Comment top

The 4(1H)quinolone structure plays an extremely important role in the field of pharmaceutical chemistry. These compounds have been used as precursors for anticancer agents, anti-malarial agents and reversible (H+/K+) ATPase inhibitors (Ruchelman et al.,2003). 5-arylaminomethylene-2,2-dimethyl-1,3-dioxane-4,6-diones are the key intermediates which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis (Cassis et al., 1985).

In the structure of the title molecule (Fig. 1), it is approximately planar with the dihedral angles of 3.11 (4)° and 2.12 (4)° between the connecting aminomethylene unit and the planar part of the dioxane ring, and between the dimethoxybenzyl ring and the aminomethylene group, respectively. Besides, the dioxane ring of the title compound exhibits a half-boat conformation, in which the C atom between the dioxane O atoms is -0.5471 (8) Å out-of-plane.

The intramolecular N—H···O hydrogen bond (Table 1) is stabilizing the planar conformation in the molecule. Intermolecular weak C—H···O hydrogen bonding contacts (Table 1) result in the formation of sheets running parallel to the a-b plane in the crystal structure (Fig. 2).

Related literature top

For the synthesis of related compounds, see: Cassis et al. (1985). For the synthesis of related antitumor precursors, see Ruchelman et al. (2003). For the structure of 5-(aminomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, see: da Silva et al. (2006). For Meldrum's acid, see: Meldrum (1908).

Experimental top

A solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) and methylorthoformate was heated to reflux for two hours and immediately the arylamine was added in an equimolar amount relative to Meldrum's acid. The mixture was heated under reflux for another 5–8 h; single recrystallization from methanol gave the corresponding arylaminomethylene derivative as analytically pure material.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound showing the layer-like aggregation of the title molecules in the unit cell.

5-[(3,4-Dimethoxybenzyl)aminomethylene]-2,2-dimethyl-1,3-dioxane-4,6-dione top

Crystal data top

C₁₅H₁₇NO₆	F(000) = 648
M_r = 307.30	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.270 (4) Å	Cell parameters from 29 reflections
b = 12.486 (4) Å	θ = 4.4–7.7°
c = 19.529 (5) Å	µ = 0.11 mm⁻¹
β = 106.31 (3)°	T = 292 K
V = 1467.3 (11) Å³	Block, yellow
Z = 4	0.44 × 0.38 × 0.18 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.008
Radiation source: fine-focus sealed tube	θ_max = 25.4°, θ_min = 2.0°
Graphite monochromator	h = −7→7
ω/2θ scans	k = −15→0
2852 measured reflections	l = −23→8
2657 independent reflections	3 standard reflections every 150 reflections
1675 reflections with I > 2σ(I)	intensity decay: 1.8%

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)] = 0.056	Hydrogen site location: mixed
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0954P)²] where P = (F_o² + 2F_c²)/3
2657 reflections	(Δ/σ)_max < 0.001
207 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₅H₁₇NO₆	V = 1467.3 (11) Å³
M_r = 307.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.270 (4) Å	µ = 0.11 mm⁻¹
b = 12.486 (4) Å	T = 292 K
c = 19.529 (5) Å	0.44 × 0.38 × 0.18 mm
β = 106.31 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.008
2852 measured reflections	3 standard reflections every 150 reflections
2657 independent reflections	intensity decay: 1.8%
1675 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
2657 reflections	Δρ_min = −0.26 e Å⁻³
207 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 > σ(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	0.0589 (3)	0.78796 (12)	0.14968 (8)	0.0456 (5)
O2	−0.0296 (3)	0.60397 (13)	0.13307 (9)	0.0489 (5)
O3	0.3798 (3)	0.84242 (14)	0.22145 (9)	0.0522 (5)
O4	0.2084 (3)	0.47579 (14)	0.18214 (10)	0.0623 (6)
O5	1.4467 (3)	0.80170 (14)	0.40934 (10)	0.0544 (5)
O6	1.5852 (3)	0.60587 (14)	0.42558 (9)	0.0503 (5)
N1	0.7059 (3)	0.69339 (19)	0.27469 (10)	0.0403 (5)
H1N	0.677 (4)	0.761 (2)	0.2721 (13)	0.046 (8)*
C1	−0.2969 (4)	0.7333 (2)	0.08019 (14)	0.0523 (7)
H1A	−0.3797	0.6767	0.0513	0.078*
H1B	−0.3242	0.7994	0.0540	0.078*
H1C	−0.3427	0.7404	0.1229	0.078*
C2	0.0406 (5)	0.7062 (3)	0.03595 (15)	0.0674 (9)
H2A	0.1966	0.6903	0.0517	0.101*
H2B	0.0187	0.7749	0.0131	0.101*
H2C	−0.0343	0.6523	0.0027	0.101*
C3	−0.0529 (4)	0.70753 (19)	0.09947 (12)	0.0411 (6)
C4	0.2670 (4)	0.7662 (2)	0.19222 (12)	0.0389 (6)
C5	0.3347 (4)	0.65633 (19)	0.20110 (11)	0.0374 (6)
C6	0.1782 (4)	0.5710 (2)	0.17241 (13)	0.0422 (6)
C7	0.5461 (4)	0.6272 (2)	0.24184 (12)	0.0398 (6)
H7	0.5778	0.5544	0.2464	0.048*
C8	0.9280 (4)	0.66471 (19)	0.31291 (11)	0.0374 (6)
C9	1.0729 (4)	0.74811 (19)	0.34299 (11)	0.0388 (6)
H9	1.0219	0.8184	0.3384	0.047*
C10	1.2914 (4)	0.72663 (18)	0.37956 (11)	0.0392 (6)
C11	1.3659 (4)	0.61937 (18)	0.38805 (11)	0.0370 (6)
C12	1.2204 (4)	0.5382 (2)	0.35779 (12)	0.0442 (6)
H12	1.2696	0.4676	0.3626	0.053*
C13	1.0014 (4)	0.5605 (2)	0.32015 (12)	0.0445 (6)
H13	0.9050	0.5051	0.3000	0.053*
C14	1.3812 (5)	0.9112 (2)	0.39922 (15)	0.0588 (8)
H14A	1.3307	0.9266	0.3491	0.088*
H14B	1.5056	0.9562	0.4212	0.088*
H14C	1.2631	0.9245	0.4205	0.088*
C15	1.6708 (4)	0.4995 (2)	0.43247 (14)	0.0535 (7)
H15A	1.5973	0.4577	0.4603	0.080*
H15B	1.8275	0.5012	0.4557	0.080*
H15C	1.6451	0.4681	0.3860	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0390 (10)	0.0379 (10)	0.0492 (10)	0.0012 (8)	−0.0054 (8)	−0.0002 (7)
O2	0.0380 (10)	0.0398 (10)	0.0585 (11)	−0.0059 (8)	−0.0036 (8)	0.0011 (8)
O3	0.0468 (11)	0.0371 (10)	0.0602 (11)	−0.0067 (8)	−0.0054 (9)	−0.0021 (8)
O4	0.0517 (12)	0.0318 (11)	0.0890 (14)	−0.0007 (8)	−0.0040 (10)	0.0002 (9)
O5	0.0456 (11)	0.0377 (10)	0.0634 (11)	−0.0014 (8)	−0.0120 (8)	−0.0020 (8)
O6	0.0388 (10)	0.0459 (11)	0.0550 (10)	0.0053 (8)	−0.0052 (8)	−0.0005 (8)
N1	0.0345 (12)	0.0390 (13)	0.0417 (11)	0.0005 (9)	0.0012 (9)	0.0041 (9)
C1	0.0384 (15)	0.0603 (18)	0.0493 (15)	−0.0006 (13)	−0.0025 (12)	0.0020 (13)
C2	0.0541 (18)	0.097 (2)	0.0504 (15)	−0.0023 (17)	0.0130 (13)	−0.0022 (16)
C3	0.0356 (13)	0.0432 (14)	0.0392 (12)	−0.0032 (11)	0.0017 (10)	0.0001 (11)
C4	0.0371 (13)	0.0408 (14)	0.0357 (12)	−0.0019 (11)	0.0050 (10)	0.0021 (10)
C5	0.0334 (13)	0.0383 (13)	0.0366 (12)	−0.0023 (10)	0.0034 (10)	0.0010 (10)
C6	0.0338 (14)	0.0417 (15)	0.0471 (14)	−0.0016 (11)	0.0045 (11)	−0.0025 (11)
C7	0.0364 (14)	0.0424 (14)	0.0382 (12)	−0.0001 (11)	0.0063 (11)	0.0013 (10)
C8	0.0329 (13)	0.0404 (14)	0.0346 (12)	0.0006 (11)	0.0024 (9)	0.0052 (10)
C9	0.0410 (14)	0.0334 (13)	0.0377 (12)	0.0042 (11)	0.0038 (10)	0.0017 (10)
C10	0.0413 (14)	0.0378 (14)	0.0329 (11)	−0.0028 (11)	0.0011 (10)	−0.0024 (10)
C11	0.0335 (13)	0.0419 (14)	0.0320 (11)	0.0059 (11)	0.0031 (10)	0.0034 (10)
C12	0.0432 (15)	0.0351 (14)	0.0492 (14)	0.0050 (11)	0.0045 (11)	0.0021 (11)
C13	0.0425 (15)	0.0371 (14)	0.0468 (14)	−0.0042 (11)	0.0011 (11)	0.0043 (11)
C14	0.0604 (18)	0.0389 (15)	0.0644 (17)	−0.0048 (13)	−0.0030 (14)	−0.0025 (13)
C15	0.0455 (16)	0.0508 (16)	0.0572 (15)	0.0149 (13)	0.0030 (12)	0.0028 (13)

Geometric parameters (Å, º) top

O1—C4	1.363 (3)	C2—H2C	0.9600
O1—C3	1.441 (3)	C4—C5	1.432 (3)
O2—C6	1.376 (3)	C5—C7	1.389 (3)
O2—C3	1.439 (3)	C5—C6	1.450 (3)
O3—C4	1.227 (3)	C7—H7	0.9300
O4—C6	1.211 (3)	C8—C13	1.374 (4)
O5—C10	1.359 (3)	C8—C9	1.398 (3)
O5—C14	1.425 (3)	C9—C10	1.382 (3)
O6—C11	1.375 (3)	C9—H9	0.9300
O6—C15	1.424 (3)	C10—C11	1.413 (3)
N1—C7	1.318 (3)	C11—C12	1.380 (3)
N1—C8	1.428 (3)	C12—C13	1.392 (4)
N1—H1N	0.86 (3)	C12—H12	0.9300
C1—C3	1.504 (4)	C13—H13	0.9300
C1—H1A	0.9600	C14—H14A	0.9600
C1—H1B	0.9600	C14—H14B	0.9600
C1—H1C	0.9600	C14—H14C	0.9600
C2—C3	1.513 (4)	C15—H15A	0.9600
C2—H2A	0.9600	C15—H15B	0.9600
C2—H2B	0.9600	C15—H15C	0.9600

C4—O1—C3	118.37 (18)	N1—C7—C5	126.0 (2)
C6—O2—C3	118.82 (19)	N1—C7—H7	117.0
C10—O5—C14	117.26 (19)	C5—C7—H7	117.0
C11—O6—C15	117.28 (19)	C13—C8—C9	120.2 (2)
C7—N1—C8	126.4 (2)	C13—C8—N1	122.7 (2)
C7—N1—H1N	117.7 (17)	C9—C8—N1	117.1 (2)
C8—N1—H1N	115.9 (17)	C10—C9—C8	120.4 (2)
C3—C1—H1A	109.5	C10—C9—H9	119.8
C3—C1—H1B	109.5	C8—C9—H9	119.8
H1A—C1—H1B	109.5	O5—C10—C9	125.1 (2)
C3—C1—H1C	109.5	O5—C10—C11	115.5 (2)
H1A—C1—H1C	109.5	C9—C10—C11	119.5 (2)
H1B—C1—H1C	109.5	O6—C11—C12	125.4 (2)
C3—C2—H2A	109.5	O6—C11—C10	115.3 (2)
C3—C2—H2B	109.5	C12—C11—C10	119.3 (2)
H2A—C2—H2B	109.5	C11—C12—C13	121.0 (2)
C3—C2—H2C	109.5	C11—C12—H12	119.5
H2A—C2—H2C	109.5	C13—C12—H12	119.5
H2B—C2—H2C	109.5	C8—C13—C12	119.7 (2)
O2—C3—O1	110.38 (17)	C8—C13—H13	120.1
O2—C3—C1	105.8 (2)	C12—C13—H13	120.1
O1—C3—C1	106.7 (2)	O5—C14—H14A	109.5
O2—C3—C2	110.5 (2)	O5—C14—H14B	109.5
O1—C3—C2	109.8 (2)	H14A—C14—H14B	109.5
C1—C3—C2	113.5 (2)	O5—C14—H14C	109.5
O3—C4—O1	117.1 (2)	H14A—C14—H14C	109.5
O3—C4—C5	125.1 (2)	H14B—C14—H14C	109.5
O1—C4—C5	117.8 (2)	O6—C15—H15A	109.5
C7—C5—C4	121.5 (2)	O6—C15—H15B	109.5
C7—C5—C6	117.6 (2)	H15A—C15—H15B	109.5
C4—C5—C6	120.7 (2)	O6—C15—H15C	109.5
O4—C6—O2	117.6 (2)	H15A—C15—H15C	109.5
O4—C6—C5	127.0 (2)	H15B—C15—H15C	109.5
O2—C6—C5	115.4 (2)

C6—O2—C3—O1	−48.6 (3)	C6—C5—C7—N1	−176.7 (2)
C6—O2—C3—C1	−163.7 (2)	C7—N1—C8—C13	−0.4 (4)
C6—O2—C3—C2	73.1 (3)	C7—N1—C8—C9	179.0 (2)
C4—O1—C3—O2	45.3 (3)	C13—C8—C9—C10	0.7 (4)
C4—O1—C3—C1	159.8 (2)	N1—C8—C9—C10	−178.8 (2)
C4—O1—C3—C2	−76.8 (3)	C14—O5—C10—C9	−2.9 (4)
C3—O1—C4—O3	162.7 (2)	C14—O5—C10—C11	177.2 (2)
C3—O1—C4—C5	−19.1 (3)	C8—C9—C10—O5	178.4 (2)
O3—C4—C5—C7	−3.9 (4)	C8—C9—C10—C11	−1.7 (3)
O1—C4—C5—C7	178.1 (2)	C15—O6—C11—C12	1.5 (3)
O3—C4—C5—C6	171.1 (2)	C15—O6—C11—C10	−177.0 (2)
O1—C4—C5—C6	−6.9 (3)	O5—C10—C11—O6	0.3 (3)
C3—O2—C6—O4	−158.5 (2)	C9—C10—C11—O6	−179.6 (2)
C3—O2—C6—C5	24.7 (3)	O5—C10—C11—C12	−178.3 (2)
C7—C5—C6—O4	2.9 (4)	C9—C10—C11—C12	1.9 (4)
C4—C5—C6—O4	−172.3 (3)	O6—C11—C12—C13	−179.4 (2)
C7—C5—C6—O2	179.3 (2)	C10—C11—C12—C13	−1.0 (4)
C4—C5—C6—O2	4.2 (3)	C9—C8—C13—C12	0.2 (4)
C8—N1—C7—C5	−175.7 (2)	N1—C8—C13—C12	179.6 (2)
C4—C5—C7—N1	−1.6 (4)	C11—C12—C13—C8	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.86 (3)	2.11 (3)	2.744 (3)	130 (2)
C9—H9···O4ⁱ	0.93	2.40	3.309 (4)	164
C15—H15C···O3ⁱⁱ	0.96	2.59	3.528 (4)	166

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇NO₆
M_r	307.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	6.270 (4), 12.486 (4), 19.529 (5)
β (°)	106.31 (3)
V (Å³)	1467.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.44 × 0.38 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2852, 2657, 1675
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.160, 1.03
No. of reflections	2657
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.86 (3)	2.11 (3)	2.744 (3)	130 (2)
C9—H9···O4ⁱ	0.93	2.40	3.309 (4)	164
C15—H15C···O3ⁱⁱ	0.96	2.59	3.528 (4)	166

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

Acknowledgements

This research was supported financially by the State Key Laboratory of Drug Research (Shanghai Institute of Materia Medica, Chinese Academy of Sciences).

References

Cassis, R., Tapia, R. & Valderrama, J. A. (1985). Synth. Commun. 15, 125–133. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting. Abstract PA104. Google Scholar
Meldrum, A. N. (1908). J. Chem. Soc. Trans. 93, 598–601. CrossRef CAS Google Scholar
Ruchelman, A. L., Singh, S. K., Ray, A., Wu, X. H., Yang, J. M., Li, T. K., Liu, A., Liu, L. F. & LaVoie, E. J. (2003). Bioorg. Med. Chem. 11, 2061–2073. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Silva, L. E. da, Joussef, A. C., Silva, L. L., Foro, S. & Schmidt, B. (2006). Acta Cryst. E62, o3866–o3867. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Pages o1298-o1299

doi:10.1107/S1600536809017413

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

5-[(3,4-Di­meth­oxy­benzyl)­amino­methyl­ene]-2,2-di­methyl-1,3-dioxane-4,6-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5-[(3,4-Dimethoxybenzyl)aminomethylene]-2,2-dimethyl-1,3-dioxane-4,6-dione