(4S,5S)-2-(4-Chloro-phen-yl)-1,3-dioxolane-4,5-dicarboxamide.

The title compound, C(11)H(11)ClN(2)O(4), is an important inter-mediate for the preparation of platinum anti-cancer drugs. The dioxolane ring adopts a twist conformation with an equatorially attached chloro-phenyl substituent. In the crystal structure, mol-ecules 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 = 270.67

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.122

S = 1.07

2113 reflections

179 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 916 Friedel pairs

Flack parameter: 0.07 (14)

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.

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

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

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

C11H11ClN2O4	F(000) = 280
Mr = 270.67	Dx = 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

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

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(Fo2) + (0.0601P)2 + 0.0558P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2113 reflections	Δρmax = 0.20 e Å−3
179 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 916 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (14)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .