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

In the title compound, C(12)H(14)N(2)O(5), the five-membered ring adopts an envelope conformation. In the crystal structure, inter-molecular N-H⋯O inter-actions link the mol-ecules into a three-dimensional network. A weak C-H⋯π inter-action 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 = 266.25

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.132

S = 1.33

1378 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.40 e Å−3

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 ▶).

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

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

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

C12H14N2O5	F(000) = 560
Mr = 266.25	Dx = 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

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

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(Fo2) + (0.0632P)2 + 0.0799P] where P = (Fo2 + 2Fc2)/3
1378 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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	0.6259 (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)

	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)

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)

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···Cg1iv	0.98	2.82	3.640 (4)	141

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⋯Cg1iv	0.98	2.82	3.640 (4)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C2–C7 ring.