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

In the mol-ecule of the title compound, C(11)H(11)FN(2)O(4), the five-membered ring adopts an envelope conformation. An intra-molecular N-H⋯F hydrogen bond occurs. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

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

C11H11FN2O4

M = 254.22

Orthorhombic,

a = 4.8760 (5) Å

b = 9.1290 (7) Å

c = 24.8160 (9) Å

V = 1104.63 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 294 (2) K

0.40 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.978, T max = 0.987

2157 measured reflections

1301 independent reflections

898 reflections with I > 2σ(I)

R int = 0.072

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.125

S = 1.00

1301 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536808039470/hk2584sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536808039470/hk2584Isup2.hkl

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

C11H11FN2O4	F(000) = 528
Mr = 254.22	Dx = 1.529 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 4.8760 (5) Å	θ = 9–12°
b = 9.1290 (7) Å	µ = 0.13 mm−1
c = 24.8160 (9) Å	T = 294 K
V = 1104.63 (15) Å3	Block, colorless
Z = 4	0.40 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	898 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
graphite	θmax = 26.0°, θmin = 1.6°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.978, Tmax = 0.987	l = 0→30
2157 measured reflections	3 standard reflections every 120 min
1301 independent reflections	intensity decay: none

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.002P)2 + 1.775P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1301 reflections	Δρmax = 0.27 e Å−3
164 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

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
O1	0.6898 (8)	0.3384 (4)	0.36430 (13)	0.0497 (10)
O2	0.9373 (9)	0.5438 (3)	0.37339 (12)	0.0489 (10)
O3	1.1580 (8)	0.2201 (5)	0.44108 (17)	0.0576 (11)
O4	0.7161 (10)	0.6057 (4)	0.50750 (13)	0.0599 (12)
N1	0.7627 (11)	0.0954 (4)	0.44684 (15)	0.0513 (12)
H1A	0.8450	0.0144	0.4540	0.062*
H1B	0.5866	0.0979	0.4449	0.062*
N2	0.5605 (12)	0.6946 (5)	0.42850 (18)	0.0681 (16)
H2A	0.4529	0.7561	0.4441	0.082*
H2B	0.5674	0.6905	0.3939	0.082*
F1	0.4814 (11)	0.6150 (5)	0.30682 (15)	0.1054 (16)
C1	0.6335 (15)	0.5470 (7)	0.2681 (2)	0.0633 (18)
C2	0.572 (2)	0.5797 (8)	0.2158 (3)	0.083 (2)
H2	0.4353	0.6472	0.2076	0.099*
C3	0.715 (2)	0.5109 (8)	0.1758 (3)	0.088 (3)
H3	0.6700	0.5274	0.1399	0.105*
C4	0.9265 (19)	0.4170 (9)	0.1887 (2)	0.095 (3)
H4	1.0286	0.3731	0.1615	0.114*
C5	0.9875 (19)	0.3878 (8)	0.2426 (2)	0.076 (2)
H5	1.1281	0.3230	0.2511	0.092*
C6	0.8410 (14)	0.4542 (6)	0.2832 (2)	0.0539 (16)
C7	0.9126 (13)	0.4196 (6)	0.34082 (18)	0.0466 (13)
H7	1.0818	0.3617	0.3423	0.056*
C8	0.7392 (14)	0.3487 (5)	0.42137 (18)	0.0461 (14)
H8	0.5644	0.3507	0.4409	0.055*
C9	0.8871 (13)	0.4968 (5)	0.42764 (19)	0.0470 (14)
H9	1.0617	0.4826	0.4465	0.056*
C10	0.9067 (11)	0.2163 (6)	0.4389 (2)	0.0407 (12)
C11	0.7142 (14)	0.6068 (5)	0.4576 (2)	0.0492 (14)

	U11	U22	U33	U12	U13	U23
O1	0.056 (2)	0.0459 (19)	0.0467 (19)	−0.007 (2)	−0.009 (2)	0.0041 (16)
O2	0.059 (2)	0.0420 (18)	0.0451 (19)	−0.007 (2)	0.006 (2)	−0.0011 (15)
O3	0.038 (2)	0.059 (2)	0.075 (3)	−0.006 (2)	−0.003 (2)	0.007 (2)
O4	0.079 (3)	0.054 (2)	0.046 (2)	−0.016 (3)	0.003 (2)	−0.0063 (17)
N1	0.055 (3)	0.044 (2)	0.055 (2)	−0.001 (3)	−0.009 (3)	0.008 (2)
N2	0.093 (4)	0.060 (3)	0.052 (3)	0.020 (4)	0.000 (3)	−0.004 (2)
F1	0.106 (4)	0.128 (4)	0.082 (3)	0.045 (4)	−0.016 (3)	0.000 (3)
C1	0.071 (5)	0.066 (4)	0.054 (3)	0.003 (4)	−0.003 (3)	0.005 (3)
C2	0.106 (6)	0.072 (4)	0.070 (4)	−0.004 (5)	−0.022 (5)	0.017 (4)
C3	0.118 (7)	0.091 (5)	0.053 (4)	−0.021 (6)	−0.021 (5)	0.021 (4)
C4	0.108 (6)	0.134 (7)	0.043 (3)	−0.003 (7)	0.000 (4)	−0.005 (4)
C5	0.088 (5)	0.087 (5)	0.054 (4)	0.010 (5)	0.009 (4)	−0.010 (3)
C6	0.068 (4)	0.048 (3)	0.046 (3)	−0.003 (3)	0.000 (3)	0.005 (2)
C7	0.048 (3)	0.047 (3)	0.045 (3)	0.002 (3)	0.001 (3)	0.000 (2)
C8	0.063 (4)	0.037 (2)	0.038 (3)	0.003 (3)	−0.002 (3)	0.002 (2)
C9	0.056 (4)	0.042 (3)	0.043 (3)	0.001 (3)	0.002 (3)	0.003 (2)
C10	0.045 (3)	0.039 (3)	0.038 (3)	0.001 (3)	0.001 (3)	−0.002 (2)
C11	0.062 (4)	0.039 (3)	0.047 (3)	−0.009 (3)	0.002 (3)	−0.006 (2)

O1—C7	1.438 (6)	C3—C4	1.378 (11)
O1—C8	1.440 (5)	C3—H3	0.9300
O2—C7	1.398 (5)	C4—H4	0.9300
O2—C9	1.434 (5)	C5—C4	1.396 (8)
O3—C10	1.227 (6)	C5—H5	0.9300
O4—C11	1.240 (5)	C6—C1	1.372 (8)
N1—C10	1.323 (6)	C6—C5	1.376 (8)
N1—H1A	0.8600	C7—C6	1.505 (7)
N1—H1B	0.8600	C7—H7	0.9800
N2—H2A	0.8600	C8—H8	0.9800
N2—H2B	0.8600	C9—C8	1.540 (7)
F1—C1	1.363 (7)	C9—H9	0.9800
C2—C1	1.366 (7)	C10—C8	1.522 (7)
C2—H2	0.9300	C11—N2	1.313 (7)
C3—C2	1.367 (10)	C11—C9	1.507 (7)
C7—O1—C8	103.8 (4)	C5—C6—C7	118.9 (6)
C7—O2—C9	106.6 (3)	O1—C7—C6	108.5 (5)
C10—N1—H1A	120.0	O1—C7—H7	110.1
C10—N1—H1B	120.0	O2—C7—O1	104.4 (4)
H1A—N1—H1B	120.0	O2—C7—C6	113.5 (4)
C11—N2—H2A	120.0	O2—C7—H7	110.1
C11—N2—H2B	120.0	C6—C7—H7	110.1
H2A—N2—H2B	120.0	O1—C8—C10	108.6 (4)
F1—C1—C2	116.8 (7)	O1—C8—C9	103.6 (4)
F1—C1—C6	119.4 (5)	O1—C8—H8	109.9
C2—C1—C6	123.9 (7)	C9—C8—H8	109.9
C1—C2—C3	118.5 (7)	C10—C8—C9	114.6 (5)
C1—C2—H2	120.8	C10—C8—H8	109.9
C3—C2—H2	120.8	O2—C9—C8	104.3 (4)
C2—C3—C4	119.9 (6)	O2—C9—C11	111.0 (4)
C2—C3—H3	120.0	O2—C9—H9	109.8
C4—C3—H3	120.0	C8—C9—H9	109.8
C3—C4—C5	120.1 (7)	C11—C9—C8	111.9 (5)
C3—C4—H4	120.0	C11—C9—H9	109.8
C5—C4—H4	120.0	O3—C10—N1	123.2 (6)
C6—C5—C4	120.5 (7)	O3—C10—C8	121.8 (5)
C6—C5—H5	119.8	O4—C11—N2	123.9 (6)
C4—C5—H5	119.8	O4—C11—C9	118.9 (5)
C1—C6—C5	117.1 (6)	N1—C10—C8	114.8 (4)
C1—C6—C7	124.1 (5)	N2—C11—C9	117.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.86	2.32	3.089 (4)	149
N1—H1B···O3ii	0.86	2.37	3.164 (4)	153
N2—H2A···O4iii	0.86	2.09	2.944 (5)	172
N2—H2B···F1	0.86	2.31	3.130 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.86	2.32	3.089 (4)	149
N1—H1B⋯O3ii	0.86	2.37	3.164 (4)	153
N2—H2A⋯O4iii	0.86	2.09	2.944 (5)	172
N2—H2B⋯F1	0.86	2.31	3.130 (4)	160

Symmetry codes: (i) ; (ii) ; (iii) .