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

Wang, D.-C.; Bai, J.; Xu, W.; Gai, T.; Liu, H.-Q.

doi:10.1107/S1600536809027494

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1960

doi:10.1107/S1600536809027494

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

De-Cai Wang,^a ^* Jing Bai,^a Wei Xu,^a Tao Gai ^a and Hua-Quan Liu ^a

^aSchool of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: dcwang@njut.edu.cn

(Received 13 June 2009; accepted 13 July 2009; online 22 July 2009)

The title compound, C₁₁H₁₁ClN₂O₄, is an important intermediate for the preparation of platinum anticancer drugs. The dioxolane ring adopts a twist conformation with an equatorially attached chlorophenyl substituent. In the crystal structure, molecules are linked into a two-dimensional network parallel to (001) by N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₁H₁₁ClN₂O₄
M_r = 270.67
Monoclinic, P 2₁
a = 9.2780 (19) Å
b = 4.7600 (10) Å
c = 13.245 (3) Å
β = 93.15 (3)°
V = 584.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.936, T_max = 0.967
2248 measured reflections
2113 independent reflections
1694 reflections with I > 2σ(I)
R_int = 0.027
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.122
S = 1.07
2113 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 916 Friedel pairs
Flack parameter: 0.07 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.79 (4)	2.20 (4)	2.979 (5)	166 (4)
N2—H2A⋯O3ⁱⁱ	0.87 (4)	2.42 (3)	3.173 (5)	145 (3)
N2—H2B⋯O4ⁱⁱⁱ	0.81 (6)	2.26 (6)	3.012 (4)	155 (4)
C9—H9⋯O4ⁱⁱⁱ	0.98	2.31	3.075 (4)	135
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y-1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027494/ci2828sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027494/ci2828Isup2.hkl

checkCIF report

Comment top

Platinum antitumor drug is one kind of the most effective anticancer agents currently available. (2S,3S)-Diethyl 2,3-O-alkyltartrate analogues are 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 have synthesized the title compound and reported herein its crystal structure.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The dioxolane ring adopts a twist conformation and the chlorophenyl unit is equatorially attached.

In the crystal structure, N—H···O and C—H···O intermolecular hydrogen bonds (Table 1) link the molecules to form a two-dimensional network (Fig. 2) parallel to the (001).

Related literature top

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

Experimental top

4-Chlorobenzaldehyde (278 mg, 1.98 mmol), (2S,3S)-diethyltartrate (378 mg,1.84 mmol) and cyclohexane (10 ml) were placed in a round-bottomed flask, and 4-methylbenzenesulfonic acid (30 mg) was added. The flask was fitted with a water-distributor. The mixture was heated under reflux for 3 h. The reaction mixture was cooled to room temperature, and then transfered into a separatory funnel, washed with water (200 ml) and extracted with acetate (200 ml). The organic phase was distilled under pressure, and the residual was dissolved in anhydrous ethanol (50 ml). Then, a current of dry ammonia was passed through the reaction mixture at room temperature for about 4 h. The reaction mixture was then added dropwise to a vigorously stirred water (600 ml). The resulting colourless precipitate was obtained by filtration and dried in vacuo (Kim et al., 1994). Single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution after two weeks.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₁H₁₁ClN₂O₄	F(000) = 280
M_r = 270.67	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 9.2780 (19) Å	θ = 9–13°
b = 4.760 (1) Å	µ = 0.34 mm⁻¹
c = 13.245 (3) Å	T = 293 K
β = 93.15 (3)°	Block, colourless
V = 584.1 (2) Å³	0.20 × 0.20 × 0.10 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	1694 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.3°, θ_min = 1.5°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −5→5
T_min = 0.936, T_max = 0.967	l = −15→15
2248 measured reflections	3 standard reflections every 200 reflections
2113 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0601P)² + 0.0558P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2113 reflections	Δρ_max = 0.20 e Å⁻³
179 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 916 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (14)

Crystal data top

C₁₁H₁₁ClN₂O₄	V = 584.1 (2) Å³
M_r = 270.67	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.2780 (19) Å	µ = 0.34 mm⁻¹
b = 4.760 (1) Å	T = 293 K
c = 13.245 (3) Å	0.20 × 0.20 × 0.10 mm
β = 93.15 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1694 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.027
T_min = 0.936, T_max = 0.967	3 standard reflections every 200 reflections
2248 measured reflections	intensity decay: 1%
2113 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	Δρ_max = 0.20 e Å⁻³
S = 1.07	Δρ_min = −0.27 e Å⁻³
2113 reflections	Absolute structure: Flack (1983), 916 Friedel pairs
179 parameters	Absolute structure parameter: 0.07 (14)
1 restraint

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
Cl1	0.35368 (14)	−0.0236 (4)	−0.21514 (8)	0.0925 (5)
O1	0.2854 (2)	0.2859 (5)	0.26692 (18)	0.0475 (6)
O2	0.0917 (2)	0.0071 (5)	0.24181 (16)	0.0461 (6)
O3	0.3515 (3)	0.0218 (6)	0.51614 (17)	0.0568 (7)
O4	−0.0323 (3)	0.4727 (5)	0.3827 (2)	0.0657 (8)
N1	0.4522 (4)	−0.0804 (9)	0.3700 (3)	0.0597 (10)
H1A	0.516 (4)	−0.168 (8)	0.397 (3)	0.038 (10)*
H1B	0.451 (4)	−0.069 (10)	0.305 (3)	0.064 (13)*
N2	−0.1472 (4)	0.0634 (7)	0.3925 (3)	0.0458 (7)
H2A	−0.230 (4)	0.139 (7)	0.403 (2)	0.034 (9)*
H2B	−0.140 (5)	−0.105 (12)	0.399 (3)	0.071 (15)*
C1	0.2948 (4)	0.0470 (10)	−0.0955 (3)	0.0573 (10)
C2	0.3508 (5)	−0.1037 (10)	−0.0134 (3)	0.0675 (12)
H2	0.4179	−0.2455	−0.0224	0.081*
C3	0.3072 (4)	−0.0438 (10)	0.0813 (3)	0.0618 (10)
H3	0.3440	−0.1476	0.1363	0.074*
C4	0.2085 (4)	0.1701 (7)	0.0964 (3)	0.0467 (9)
C5	0.1527 (4)	0.3126 (9)	0.0133 (3)	0.0614 (11)
H5	0.0852	0.4541	0.0216	0.074*
C6	0.1949 (5)	0.2500 (11)	−0.0830 (3)	0.0701 (12)
H6	0.1549	0.3468	−0.1387	0.084*
C7	0.1632 (4)	0.2384 (7)	0.1998 (3)	0.0471 (8)
H7	0.1002	0.4038	0.1976	0.057*
C8	0.2436 (3)	0.2201 (7)	0.3666 (2)	0.0392 (7)
H8	0.2264	0.3935	0.4039	0.047*
C9	0.1005 (3)	0.0548 (7)	0.3490 (2)	0.0378 (7)
H9	0.1064	−0.1248	0.3852	0.045*
C10	−0.0327 (3)	0.2166 (7)	0.3777 (3)	0.0395 (8)
C11	0.3560 (3)	0.0449 (8)	0.4236 (2)	0.0423 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1056 (9)	0.1139 (10)	0.0597 (6)	−0.0231 (10)	0.0197 (6)	−0.0196 (7)
O1	0.0522 (13)	0.0425 (14)	0.0473 (13)	−0.0157 (11)	−0.0015 (11)	0.0055 (11)
O2	0.0474 (12)	0.0375 (13)	0.0539 (13)	−0.0122 (12)	0.0066 (10)	−0.0116 (12)
O3	0.0565 (14)	0.0719 (19)	0.0423 (13)	−0.0098 (15)	0.0051 (11)	0.0030 (14)
O4	0.0582 (15)	0.0206 (12)	0.120 (2)	0.0031 (12)	0.0207 (14)	−0.0055 (15)
N1	0.055 (2)	0.074 (3)	0.050 (2)	0.0199 (19)	−0.0040 (17)	−0.0013 (18)
N2	0.0402 (17)	0.0289 (17)	0.069 (2)	0.0016 (14)	0.0126 (14)	0.0046 (14)
C1	0.057 (2)	0.064 (3)	0.051 (2)	−0.019 (2)	0.0029 (17)	−0.008 (2)
C2	0.071 (3)	0.065 (3)	0.066 (3)	0.011 (2)	−0.003 (2)	−0.019 (2)
C3	0.078 (3)	0.058 (2)	0.048 (2)	0.012 (2)	−0.0093 (18)	−0.003 (2)
C4	0.049 (2)	0.0377 (19)	0.053 (2)	−0.0036 (16)	−0.0039 (17)	−0.0016 (16)
C5	0.057 (2)	0.061 (3)	0.066 (3)	0.009 (2)	0.0015 (19)	0.012 (2)
C6	0.073 (3)	0.082 (3)	0.055 (2)	−0.005 (3)	−0.006 (2)	0.016 (2)
C7	0.049 (2)	0.0352 (18)	0.057 (2)	0.0005 (17)	−0.0044 (17)	0.0031 (16)
C8	0.0428 (18)	0.0303 (17)	0.0450 (18)	−0.0061 (15)	0.0073 (15)	−0.0031 (14)
C9	0.0388 (16)	0.0245 (15)	0.0500 (19)	−0.0048 (14)	0.0021 (14)	−0.0002 (13)
C10	0.0395 (17)	0.0312 (19)	0.0479 (19)	−0.0016 (15)	0.0023 (15)	0.0005 (15)
C11	0.0343 (16)	0.045 (2)	0.0475 (19)	−0.0100 (16)	0.0032 (14)	−0.0074 (17)

Geometric parameters (Å, º) top

Cl1—C1	1.738 (4)	C2—C3	1.370 (5)
O1—C7	1.420 (4)	C2—H2	0.93
O1—C8	1.431 (4)	C3—C4	1.391 (5)
O2—C7	1.415 (4)	C3—H3	0.93
O2—C9	1.436 (4)	C4—C5	1.370 (5)
O3—C11	1.233 (4)	C4—C7	1.490 (5)
O4—C10	1.221 (4)	C5—C6	1.387 (6)
N1—C11	1.313 (5)	C5—H5	0.93
N1—H1A	0.79 (4)	C6—H6	0.93
N1—H1B	0.86 (4)	C7—H7	0.98
N2—C10	1.312 (5)	C8—C11	1.506 (5)
N2—H2A	0.86 (3)	C8—C9	1.550 (4)
N2—H2B	0.81 (6)	C8—H8	0.98
C1—C6	1.355 (6)	C9—C10	1.522 (4)
C1—C2	1.379 (6)	C9—H9	0.98

C7—O1—C8	107.2 (2)	C5—C6—H6	120.2
C7—O2—C9	105.3 (2)	O2—C7—O1	104.7 (3)
C11—N1—H1A	120 (3)	O2—C7—C4	110.7 (3)
C11—N1—H1B	123 (3)	O1—C7—C4	110.8 (3)
H1A—N1—H1B	117 (4)	O2—C7—H7	110.2
C10—N2—H2A	122 (2)	O1—C7—H7	110.2
C10—N2—H2B	121 (3)	C4—C7—H7	110.2
H2A—N2—H2B	117 (4)	O1—C8—C11	111.6 (3)
C6—C1—C2	120.4 (4)	O1—C8—C9	104.2 (2)
C6—C1—Cl1	120.0 (3)	C11—C8—C9	111.0 (3)
C2—C1—Cl1	119.6 (3)	O1—C8—H8	109.9
C3—C2—C1	119.7 (4)	C11—C8—H8	109.9
C3—C2—H2	120.1	C9—C8—H8	109.9
C1—C2—H2	120.1	O2—C9—C10	108.9 (2)
C2—C3—C4	121.0 (4)	O2—C9—C8	103.3 (2)
C2—C3—H3	119.5	C10—C9—C8	114.0 (3)
C4—C3—H3	119.5	O2—C9—H9	110.1
C5—C4—C3	118.0 (4)	C10—C9—H9	110.1
C5—C4—C7	121.2 (3)	C8—C9—H9	110.1
C3—C4—C7	120.9 (3)	O4—C10—N2	123.2 (3)
C4—C5—C6	121.3 (4)	O4—C10—C9	121.2 (3)
C4—C5—H5	119.4	N2—C10—C9	115.5 (3)
C6—C5—H5	119.4	O3—C11—N1	123.9 (3)
C1—C6—C5	119.7 (4)	O3—C11—C8	119.2 (3)
C1—C6—H6	120.2	N1—C11—C8	116.9 (3)

C6—C1—C2—C3	−1.3 (6)	C3—C4—C7—O1	52.9 (5)
Cl1—C1—C2—C3	178.4 (3)	C7—O1—C8—C11	134.7 (3)
C1—C2—C3—C4	−0.9 (7)	C7—O1—C8—C9	14.8 (3)
C2—C3—C4—C5	2.1 (6)	C7—O2—C9—C10	91.5 (3)
C2—C3—C4—C7	−178.9 (4)	C7—O2—C9—C8	−30.0 (3)
C3—C4—C5—C6	−1.2 (6)	O1—C8—C9—O2	9.3 (3)
C7—C4—C5—C6	179.8 (4)	C11—C8—C9—O2	−111.0 (3)
C2—C1—C6—C5	2.2 (6)	O1—C8—C9—C10	−108.7 (3)
Cl1—C1—C6—C5	−177.5 (3)	C11—C8—C9—C10	130.9 (3)
C4—C5—C6—C1	−1.0 (7)	O2—C9—C10—O4	−93.1 (4)
C9—O2—C7—O1	40.4 (3)	C8—C9—C10—O4	21.7 (5)
C9—O2—C7—C4	159.7 (3)	O2—C9—C10—N2	84.4 (4)
C8—O1—C7—O2	−34.2 (3)	C8—C9—C10—N2	−160.8 (3)
C8—O1—C7—C4	−153.5 (3)	O1—C8—C11—O3	164.5 (3)
C5—C4—C7—O2	116.2 (4)	C9—C8—C11—O3	−79.7 (4)
C3—C4—C7—O2	−62.8 (4)	O1—C8—C11—N1	−17.0 (4)
C5—C4—C7—O1	−128.1 (4)	C9—C8—C11—N1	98.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.79 (4)	2.20 (4)	2.979 (5)	166 (4)
N2—H2A···O3ⁱⁱ	0.87 (4)	2.42 (3)	3.173 (5)	145 (3)
N2—H2B···O4ⁱⁱⁱ	0.81 (6)	2.26 (6)	3.012 (4)	155 (4)
C9—H9···O4ⁱⁱⁱ	0.98	2.31	3.075 (4)	135

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁ClN₂O₄
M_r	270.67
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.2780 (19), 4.760 (1), 13.245 (3)
β (°)	93.15 (3)
V (Å³)	584.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.936, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	2248, 2113, 1694
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.122, 1.07
No. of reflections	2113
No. of parameters	179
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.27
Absolute structure	Flack (1983), 916 Friedel pairs
Absolute structure parameter	0.07 (14)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.79 (4)	2.20 (4)	2.979 (5)	166 (4)
N2—H2A···O3ⁱⁱ	0.87 (4)	2.42 (3)	3.173 (5)	145 (3)
N2—H2B···O4ⁱⁱⁱ	0.81 (6)	2.26 (6)	3.012 (4)	155 (4)
C9—H9···O4ⁱⁱⁱ	0.98	2.31	3.075 (4)	135

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

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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