(4S,5S)-2-(3-Methoxy­phen­yl)-1,3-dioxolane-4,5-dicarboxamide

Wang, D.-C.; Ge, T.; Wu, W.-Y.; Xu, W.; Yang, Z.

doi:10.1107/S1600536809032991

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2230

doi:10.1107/S1600536809032991

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(4S,5S)-2-(3-Methoxyphenyl)-1,3-dioxolane-4,5-dicarboxamide

De-Cai Wang,^a ^* Tao Ge,^a Wen-Yuan Wu,^b Wei Xu ^a and Zheng Yang ^a

^aState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: dcwang@njut.edu.cn

(Received 29 June 2009; accepted 19 August 2009; online 26 August 2009)

In the title compound, C₁₂H₁₄N₂O₅, the five-membered ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O interactions link the molecules into a three-dimensional network. A weak C—H⋯π interaction is also found.

Related literature

For general background, see: Kim et al. (1994 ); Pandey et al. (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄N₂O₅
M_r = 266.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.2340 (18) Å
b = 9.852 (2) Å
c = 14.266 (3) Å
V = 1297.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.971, T_max = 0.979
2599 measured reflections
1378 independent reflections
1157 reflections with I > 2σ(I)
R_int = 0.027
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.132
S = 1.33
1378 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O5ⁱ	0.86	2.33	3.076 (4)	145
N2—H2A⋯O4ⁱ	0.86	2.13	2.926 (4)	153
N1—H1B⋯O2ⁱⁱ	0.86	2.31	3.045 (4)	143
N1—H1A⋯O5ⁱⁱⁱ	0.86	2.20	2.952 (4)	146
C9—H9A⋯Cg1^iv	0.98	2.82	3.640 (4)	141
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of the C2–C7 ring.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032991/hk2731sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032991/hk2731Isup2.hkl

checkCIF report

Comment top

Antitumor platinum drug is one kind of the most effective anticancer agents currently available. (2S,3S)-Diethyl 2,3-O-alkyltartrate analogues are the starting materials for the syntheses of platinum complexes with antitumor activity (Kim et al., 1994) and are also important intermediates in organic syntheses (Pandey et al., 1997). As part of our studies on the syntheses and characterizations of these compounds, we report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar, while ring B (O2/O3/C8-C10) adopts envelope conformation with atom O2 displaced by 0.456 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular N-H···O interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. A weak C—H···π interaction (Table 1) is also found.

Related literature top

For general background, see: Kim et al. (1994); Pandey et al. (1997). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the C2–C7 ring.

Experimental top

For the preparation of the title compound, a mixture of (2S,3S)-diethyl- tartrate (500 mg, 2.43 mmol), 3-methoxybenzaldehyde (331 mg, 2.43 mmol), anhydrous copper(II) sulfate (776 mg, 2.86 mmol) and one drop of methanesulfonic acid in anhydrous toluene (8 ml) was stirred at room temperature for 8 h. Anhydrous magnesium sulfate (30 mg) was added to the reaction mixture, which was then stirred for 20 min. Then, the resulting colorless precipitate was obtained by evaporation and dried in the vacuo (yield; 83%). The obtained colorless product (654 mg, 2 mmol) was dissolved in anhydrous ethanol (40 ml), and a current of dry ammonia, dried by calcium cholride was passed into the reaction mixture at room temperature for 4 h. Then, the reaction mixture was filtered and the resulting product was evaporated to dryness. Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution after four weeks.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

(4S,5S)-2-(3-Methoxyphenyl)-1,3-dioxolane-4,5-dicarboxamide top

Crystal data top

C₁₂H₁₄N₂O₅	F(000) = 560
M_r = 266.25	D_x = 1.363 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.2340 (18) Å	θ = 9–13°
b = 9.852 (2) Å	µ = 0.11 mm⁻¹
c = 14.266 (3) Å	T = 294 K
V = 1297.8 (5) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1157 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.3°, θ_min = 2.5°
ω/2θ scans	h = −11→0
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.971, T_max = 0.979	l = −17→0
2599 measured reflections	3 standard reflections every 120 min
1378 independent reflections	intensity decay: 1%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.33	w = 1/[σ²(F_o²) + (0.0632P)² + 0.0799P] where P = (F_o² + 2F_c²)/3
1378 reflections	(Δ/σ)_max < 0.001
170 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₂H₁₄N₂O₅	V = 1297.8 (5) Å³
M_r = 266.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.2340 (18) Å	µ = 0.11 mm⁻¹
b = 9.852 (2) Å	T = 294 K
c = 14.266 (3) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1157 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.027
T_min = 0.971, T_max = 0.979	3 standard reflections every 120 min
2599 measured reflections	intensity decay: 1%
1378 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.33	Δρ_max = 0.31 e Å⁻³
1378 reflections	Δρ_min = −0.40 e Å⁻³
170 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	0.6259 (4)	0.9009 (4)	−0.2515 (2)	0.085 (2)
O2	0.5311 (3)	0.7583 (2)	0.08959 (15)	0.0374 (6)
O3	0.7763 (3)	0.7304 (2)	0.10000 (19)	0.0431 (6)
O4	0.6719 (5)	0.3876 (3)	0.0578 (3)	0.0835 (13)
O5	0.5534 (3)	0.5637 (2)	0.30153 (17)	0.0495 (7)
N1	0.8069 (4)	0.5351 (3)	−0.0253 (2)	0.0600 (11)
H1A	0.8224	0.4786	−0.0701	0.072*
H1B	0.8429	0.6155	−0.0279	0.072*
N2	0.4593 (4)	0.7713 (3)	0.2737 (2)	0.0461 (8)
H2A	0.4389	0.7854	0.3317	0.055*
H2B	0.4395	0.8322	0.2324	0.055*
C1	0.5709 (6)	0.7727 (7)	−0.2635 (3)	0.093 (12)
H1C	0.5441	0.7602	−0.3280	0.140*
H1D	0.4871	0.7613	−0.2245	0.140*
H1E	0.6429	0.7069	−0.2466	0.140*
C2	0.6605 (5)	0.9407 (5)	−0.1622 (3)	0.0582 (12)
C3	0.7152 (6)	1.0709 (5)	−0.1530 (3)	0.0679 (15)
H3A	0.7253	1.1252	−0.2059	0.081*
C4	0.7541 (8)	1.1201 (4)	−0.0684 (4)	0.0788 (18)
H4A	0.7932	1.2068	−0.0638	0.095*
C5	0.7366 (6)	1.0431 (4)	0.0109 (3)	0.0581 (12)
H5A	0.7614	1.0782	0.0692	0.070*
C6	0.6820 (4)	0.9131 (3)	0.0036 (2)	0.0380 (8)
C7	0.6436 (4)	0.8611 (4)	−0.0833 (2)	0.0444 (9)
H7A	0.6069	0.7735	−0.0883	0.053*
C8	0.6654 (4)	0.8314 (3)	0.0910 (2)	0.0355 (8)
H8A	0.6676	0.8918	0.1456	0.043*
C9	0.5521 (4)	0.6389 (3)	0.1436 (2)	0.0334 (8)
H9A	0.4904	0.5665	0.1186	0.040*
C10	0.7109 (4)	0.6039 (3)	0.1246 (3)	0.0385 (8)
H10A	0.7553	0.5695	0.1823	0.046*
C11	0.7276 (5)	0.4985 (4)	0.0474 (3)	0.0469 (10)
C12	0.5210 (4)	0.6565 (3)	0.2480 (3)	0.0349 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.076 (2)	0.142 (3)	0.0376 (13)	−0.018 (2)	−0.0052 (15)	0.0087 (18)
O2	0.0403 (13)	0.0370 (12)	0.0349 (12)	−0.0019 (11)	−0.0030 (12)	0.0073 (11)
O3	0.0365 (13)	0.0359 (12)	0.0569 (16)	0.0001 (11)	−0.0015 (12)	0.0047 (12)
O4	0.128 (3)	0.0379 (16)	0.084 (2)	−0.0130 (19)	0.065 (2)	−0.0087 (16)
O5	0.0698 (18)	0.0423 (13)	0.0363 (13)	0.0070 (14)	0.0056 (14)	0.0088 (11)
N1	0.084 (3)	0.0436 (18)	0.053 (2)	−0.0035 (19)	0.038 (2)	−0.0072 (16)
N2	0.0574 (19)	0.0420 (16)	0.0390 (17)	0.0054 (17)	0.0148 (15)	0.0005 (13)
C1	0.065 (3)	0.165 (7)	0.049 (2)	−0.063 (4)	0.031 (2)	−0.035 (4)
C2	0.047 (2)	0.093 (3)	0.0348 (19)	0.010 (3)	0.0024 (18)	0.009 (2)
C3	0.091 (4)	0.053 (3)	0.060 (3)	0.021 (3)	0.029 (3)	0.023 (2)
C4	0.136 (5)	0.034 (2)	0.066 (3)	0.001 (3)	0.046 (3)	0.008 (2)
C5	0.088 (3)	0.036 (2)	0.050 (2)	−0.003 (2)	0.017 (2)	−0.0037 (18)
C6	0.044 (2)	0.0334 (17)	0.0366 (18)	0.0001 (15)	0.0056 (16)	0.0035 (15)
C7	0.043 (2)	0.052 (2)	0.0388 (19)	−0.0026 (18)	0.0046 (18)	0.0007 (18)
C8	0.0388 (18)	0.0318 (16)	0.0360 (17)	0.0027 (14)	−0.0012 (17)	0.0020 (15)
C9	0.0400 (19)	0.0285 (16)	0.0318 (17)	−0.0028 (15)	−0.0019 (16)	0.0024 (13)
C10	0.044 (2)	0.0333 (17)	0.0381 (18)	0.0026 (16)	0.0075 (16)	0.0042 (15)
C11	0.059 (3)	0.0342 (18)	0.048 (2)	0.0034 (18)	0.023 (2)	0.0064 (16)
C12	0.0405 (19)	0.0309 (16)	0.0332 (15)	−0.0022 (15)	0.0019 (16)	−0.0011 (15)

Geometric parameters (Å, º) top

O1—C1	1.372 (7)	C2—C7	1.380 (5)
O1—C2	1.371 (5)	C2—C3	1.385 (7)
O2—C8	1.434 (4)	C3—C4	1.350 (8)
O2—C9	1.419 (4)	C3—H3A	0.9300
O3—C8	1.434 (4)	C4—C5	1.371 (6)
O3—C10	1.429 (4)	C4—H4A	0.9300
O4—C11	1.217 (5)	C5—C6	1.380 (5)
O5—C12	1.228 (4)	C5—H5A	0.9300
N1—C11	1.320 (5)	C6—C7	1.387 (5)
N1—H1A	0.8600	C6—C8	1.492 (5)
N1—H1B	0.8600	C7—H7A	0.9300
N2—C12	1.318 (4)	C8—H8A	0.9800
N2—H2A	0.8600	C9—C12	1.527 (5)
N2—H2B	0.8600	C9—C10	1.531 (5)
C1—H1C	0.9600	C9—H9A	0.9800
C1—H1D	0.9600	C10—C11	1.521 (5)
C1—H1E	0.9600	C10—H10A	0.9800

C2—O1—C1	117.8 (4)	C7—C6—C8	121.4 (3)
C9—O2—C8	106.9 (2)	C2—C7—C6	119.3 (4)
C10—O3—C8	109.0 (3)	C2—C7—H7A	120.3
C11—N1—H1A	120.0	C6—C7—H7A	120.3
C11—N1—H1B	120.0	O2—C8—O3	105.6 (2)
H1A—N1—H1B	120.0	O2—C8—C6	110.4 (3)
C12—N2—H2A	120.0	O3—C8—C6	112.1 (3)
C12—N2—H2B	120.0	O2—C8—H8A	109.6
H2A—N2—H2B	120.0	O3—C8—H8A	109.6
O1—C1—H1C	109.5	C6—C8—H8A	109.6
O1—C1—H1D	109.5	O2—C9—C12	114.2 (3)
H1C—C1—H1D	109.5	O2—C9—C10	102.8 (3)
O1—C1—H1E	109.5	C12—C9—C10	112.2 (3)
H1C—C1—H1E	109.5	O2—C9—H9A	109.1
H1D—C1—H1E	109.5	C12—C9—H9A	109.1
O1—C2—C7	124.7 (5)	C10—C9—H9A	109.1
O1—C2—C3	115.9 (4)	O3—C10—C11	112.0 (3)
C7—C2—C3	119.4 (4)	O3—C10—C9	104.6 (3)
C4—C3—C2	120.9 (4)	C11—C10—C9	112.3 (3)
C4—C3—H3A	119.5	O3—C10—H10A	109.3
C2—C3—H3A	119.5	C11—C10—H10A	109.3
C3—C4—C5	120.5 (4)	C9—C10—H10A	109.3
C3—C4—H4A	119.7	O4—C11—N1	125.1 (4)
C5—C4—H4A	119.7	O4—C11—C10	118.8 (3)
C4—C5—C6	119.6 (4)	N1—C11—C10	116.0 (3)
C4—C5—H5A	120.2	O5—C12—N2	124.9 (3)
C6—C5—H5A	120.2	O5—C12—C9	118.4 (3)
C5—C6—C7	120.2 (3)	N2—C12—C9	116.7 (3)
C5—C6—C8	118.4 (3)

C1—O1—C2—C7	−0.1 (7)	C5—C6—C8—O3	−104.0 (4)
C1—O1—C2—C3	−179.8 (5)	C7—C6—C8—O3	76.1 (4)
O1—C2—C3—C4	−179.3 (5)	C8—O2—C9—C12	88.2 (3)
C7—C2—C3—C4	1.0 (8)	C8—O2—C9—C10	−33.7 (3)
C2—C3—C4—C5	−1.7 (9)	C8—O3—C10—C11	114.2 (3)
C3—C4—C5—C6	1.6 (8)	C8—O3—C10—C9	−7.6 (4)
C4—C5—C6—C7	−0.7 (7)	O2—C9—C10—O3	25.2 (3)
C4—C5—C6—C8	179.5 (5)	C12—C9—C10—O3	−98.0 (3)
O1—C2—C7—C6	−179.7 (4)	O2—C9—C10—C11	−96.5 (3)
C3—C2—C7—C6	−0.1 (6)	C12—C9—C10—C11	140.3 (3)
C5—C6—C7—C2	−0.1 (6)	O3—C10—C11—O4	−177.2 (4)
C8—C6—C7—C2	179.8 (4)	C9—C10—C11—O4	−59.9 (5)
C9—O2—C8—O3	29.8 (3)	O3—C10—C11—N1	4.8 (5)
C9—O2—C8—C6	151.1 (3)	C9—C10—C11—N1	122.1 (4)
C10—O3—C8—O2	−12.7 (3)	O2—C9—C12—O5	−171.1 (3)
C10—O3—C8—C6	−132.9 (3)	C10—C9—C12—O5	−54.6 (4)
C5—C6—C8—O2	138.5 (4)	O2—C9—C12—N2	9.5 (5)
C7—C6—C8—O2	−41.3 (4)	C10—C9—C12—N2	126.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O5ⁱ	0.86	2.33	3.076 (4)	145
N2—H2A···O4ⁱ	0.86	2.13	2.926 (4)	153
N1—H1B···O2ⁱⁱ	0.86	2.31	3.045 (4)	143
N1—H1A···O5ⁱⁱⁱ	0.86	2.20	2.952 (4)	146
C9—H9A···Cg1^iv	0.98	2.82	3.640 (4)	141

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) −x+3/2, −y+1, z−1/2; (iv) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂O₅
M_r	266.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	9.2340 (18), 9.852 (2), 14.266 (3)
V (Å³)	1297.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.971, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	2599, 1378, 1157
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.132, 1.33
No. of reflections	1378
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.40

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O5ⁱ	0.86	2.33	3.076 (4)	145
N2—H2A···O4ⁱ	0.86	2.13	2.926 (4)	153
N1—H1B···O2ⁱⁱ	0.86	2.31	3.045 (4)	143
N1—H1A···O5ⁱⁱⁱ	0.86	2.20	2.952 (4)	146
C9—H9A···Cg1^iv	0.98	2.82	3.640 (4)	141

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+3/2, −z; (iii) −x+3/2, −y+1, z−1/2; (iv) −x, y+1/2, −z+3/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University for support.

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