(3R,4R)-2,5-Dioxo-1-m-tolyl-3,4-diyl diacetate.

In the enanti-omerically pure title compound, C(15)H(15)NO(6), the five-membered ring displays a twist conformation with the local axis through the N atom. The acetyl groups are perpendicular to the ring [dihedral angles 80.3 (1) and 89.3 (1)°] and project to opposite sides. The packing is governed by two weak C-H⋯O inter-actions, forming layers of mol-ecules parallel to the ab plane.

Related literature

For the potential biological activity, pharmaceutical utility and biological effects of cyclic imides, see: Adomat & Böger (2000 ▶); Böger & Wakabayashi (1995 ▶); Birchfield & Casida (1997 ▶); Cechinel Filho, Nunes, Calixto & Yunes (1995 ▶); Cechinel Filho, de Campos, Corrêa, Yunes & Nunes (2003 ▶); López et al. (2003 ▶); Lima et al. (1999 ▶); Sami et al. (2000 ▶); Wang et al. (2000 ▶); Watanabe et al. (1998 ▶).

Experimental

Crystal data

C15H15NO6

M = 305.28

Monoclinic,

a = 8.2382 (4) Å

b = 5.5380 (3) Å

c = 16.6015 (9) Å

β = 103.664 (5)°

V = 735.98 (7) Å3

Z = 2

Cu Kα radiation

μ = 0.91 mm−1

T = 100 K

0.20 × 0.15 × 0.08 mm

Data collection

Oxford Diffraction Nova A diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2008 ▶) T min = 0.892, T max = 1.000 (expected range = 0.829–0.930)

15796 measured reflections

2790 independent reflections

2742 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.04

2790 reflections

202 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1097 Friedel pairs

Flack parameter: 0.04 (12)

Data collection: CrysAlisPro (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020637/at2801sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020637/at2801Isup2.hkl

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

C15H15NO6	F(000) = 320
Mr = 305.28	Dx = 1.378 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 13866 reflections
a = 8.2382 (4) Å	θ = 5.5–75.8°
b = 5.5380 (3) Å	µ = 0.91 mm−1
c = 16.6015 (9) Å	T = 100 K
β = 103.664 (5)°	Tablet, colourless
V = 735.98 (7) Å3	0.20 × 0.15 × 0.08 mm
Z = 2

Oxford Diffraction Nova A diffractometer	2790 independent reflections
Radiation source: Nova (Cu) X-ray Source	2742 reflections with I > 2σ(I)
mirror	Rint = 0.030
Detector resolution: 10.3543 pixels mm-1	θmax = 75.9°, θmin = 5.5°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	k = −6→6
Tmin = 0.892, Tmax = 1.000	l = −20→20
15796 measured reflections

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)] = 0.026	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.041P)2 + 0.1139P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2790 reflections	Δρmax = 0.14 e Å−3
202 parameters	Δρmin = −0.18 e Å−3
1 restraint	Absolute structure: Flack (1983), 1097 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (12)

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
N1	0.83245 (11)	0.4087 (2)	0.77707 (5)	0.0201 (2)
O1	0.95264 (12)	0.3617 (2)	0.66503 (5)	0.0332 (2)
O2	0.65363 (10)	0.53516 (17)	0.85796 (5)	0.02392 (19)
O3	0.45314 (10)	0.70803 (16)	0.70307 (5)	0.02366 (19)
O4	0.46297 (13)	1.11400 (18)	0.71612 (6)	0.0353 (2)
O5	0.73911 (11)	0.75624 (17)	0.59745 (5)	0.02408 (19)
O6	0.63863 (14)	0.5220 (2)	0.48590 (6)	0.0378 (2)
C1	0.93789 (14)	0.2475 (2)	0.83483 (7)	0.0201 (2)
C2	0.86415 (14)	0.0719 (2)	0.87400 (7)	0.0211 (2)
H2	0.7461	0.0634	0.8653	0.025*
C3	0.96605 (14)	−0.0911 (3)	0.92619 (7)	0.0225 (2)
H3	0.9175	−0.2128	0.9534	0.027*
C4	1.13842 (14)	−0.0773 (3)	0.93890 (7)	0.0228 (2)
H4	1.2066	−0.1920	0.9739	0.027*
C5	1.21311 (14)	0.1025 (2)	0.90112 (7)	0.0222 (2)
C6	1.11073 (15)	0.2667 (2)	0.84868 (7)	0.0221 (2)
H6	1.1589	0.3912	0.8225	0.026*
C7	0.84338 (14)	0.4369 (3)	0.69489 (7)	0.0232 (2)
C8	0.69155 (14)	0.5797 (2)	0.64972 (7)	0.0215 (2)
H8	0.6045	0.4694	0.6169	0.026*
C9	0.62962 (14)	0.6982 (2)	0.71900 (7)	0.0211 (2)
H9	0.6769	0.8647	0.7290	0.025*
C10	0.69933 (14)	0.5396 (2)	0.79435 (7)	0.0203 (2)
C11	0.38285 (15)	0.9315 (3)	0.70241 (7)	0.0259 (3)
C12	0.19739 (16)	0.9069 (3)	0.68349 (9)	0.0356 (3)
H12A	0.1653	0.8170	0.7282	0.053*
H12B	0.1588	0.8199	0.6311	0.053*
H12C	0.1463	1.0676	0.6788	0.053*
C13	0.70695 (15)	0.7034 (3)	0.51479 (7)	0.0252 (3)
C14	0.77036 (16)	0.9016 (3)	0.46948 (8)	0.0314 (3)
H14A	0.8918	0.8869	0.4779	0.047*
H14B	0.7432	1.0580	0.4906	0.047*
H14C	0.7177	0.8899	0.4102	0.047*
C15	1.40119 (15)	0.1163 (3)	0.91705 (8)	0.0317 (3)
H15A	1.4327	0.2568	0.8882	0.048*
H15B	1.4438	−0.0310	0.8966	0.048*
H15C	1.4492	0.1322	0.9767	0.048*

	U11	U22	U33	U12	U13	U23
N1	0.0208 (4)	0.0202 (5)	0.0192 (4)	0.0022 (4)	0.0047 (3)	0.0014 (4)
O1	0.0348 (5)	0.0416 (6)	0.0264 (4)	0.0167 (4)	0.0137 (4)	0.0088 (4)
O2	0.0247 (4)	0.0258 (5)	0.0224 (4)	−0.0010 (3)	0.0078 (3)	−0.0023 (4)
O3	0.0208 (4)	0.0199 (5)	0.0293 (4)	0.0049 (3)	0.0040 (3)	−0.0012 (4)
O4	0.0435 (5)	0.0218 (5)	0.0354 (5)	0.0086 (4)	−0.0010 (4)	−0.0048 (4)
O5	0.0279 (4)	0.0234 (5)	0.0201 (4)	−0.0003 (4)	0.0041 (3)	0.0043 (3)
O6	0.0587 (6)	0.0312 (5)	0.0242 (4)	−0.0094 (5)	0.0113 (4)	−0.0017 (4)
C1	0.0242 (5)	0.0179 (6)	0.0175 (5)	0.0023 (5)	0.0033 (4)	−0.0004 (5)
C2	0.0218 (5)	0.0217 (7)	0.0197 (5)	−0.0014 (5)	0.0045 (4)	−0.0015 (5)
C3	0.0277 (5)	0.0204 (6)	0.0195 (5)	−0.0025 (5)	0.0058 (4)	0.0008 (5)
C4	0.0270 (5)	0.0227 (6)	0.0180 (5)	0.0039 (5)	0.0038 (4)	0.0016 (5)
C5	0.0221 (5)	0.0254 (6)	0.0190 (5)	0.0000 (5)	0.0044 (4)	−0.0019 (5)
C6	0.0235 (5)	0.0225 (6)	0.0208 (5)	−0.0005 (5)	0.0066 (4)	0.0025 (5)
C7	0.0253 (5)	0.0228 (6)	0.0219 (5)	0.0020 (5)	0.0063 (4)	0.0028 (5)
C8	0.0243 (5)	0.0192 (6)	0.0211 (5)	0.0019 (5)	0.0058 (4)	0.0019 (5)
C9	0.0209 (5)	0.0191 (6)	0.0225 (5)	0.0014 (5)	0.0040 (4)	−0.0003 (5)
C10	0.0198 (5)	0.0178 (6)	0.0225 (5)	−0.0013 (4)	0.0034 (4)	−0.0017 (5)
C11	0.0337 (6)	0.0238 (7)	0.0186 (5)	0.0096 (6)	0.0030 (4)	−0.0025 (5)
C12	0.0298 (6)	0.0397 (9)	0.0357 (6)	0.0147 (7)	0.0046 (5)	−0.0028 (7)
C13	0.0285 (6)	0.0256 (7)	0.0219 (5)	0.0036 (5)	0.0065 (4)	0.0043 (5)
C14	0.0374 (6)	0.0307 (8)	0.0271 (6)	0.0003 (6)	0.0096 (5)	0.0077 (6)
C15	0.0233 (6)	0.0380 (9)	0.0333 (7)	0.0007 (5)	0.0056 (5)	0.0062 (6)

N1—C7	1.3971 (14)	C8—C9	1.5136 (16)
N1—C10	1.3996 (15)	C9—C10	1.5252 (17)
N1—C1	1.4413 (15)	C11—C12	1.4916 (17)
O1—C7	1.2000 (15)	C13—C14	1.4931 (18)
O2—C10	1.2023 (14)	C2—H2	0.9500
O3—C11	1.3654 (16)	C3—H3	0.9500
O3—C9	1.4160 (13)	C4—H4	0.9500
O4—C11	1.1990 (18)	C6—H6	0.9500
O5—C13	1.3664 (15)	C8—H8	1.0000
O5—C8	1.4225 (15)	C9—H9	1.0000
O6—C13	1.1952 (18)	C12—H12A	0.9800
C1—C2	1.3873 (17)	C12—H12B	0.9800
C1—C6	1.3918 (16)	C12—H12C	0.9800
C2—C3	1.3881 (17)	C14—H14A	0.9800
C3—C4	1.3876 (16)	C14—H14B	0.9800
C4—C5	1.3949 (18)	C14—H14C	0.9800
C5—C6	1.3962 (17)	C15—H15A	0.9800
C5—C15	1.5110 (15)	C15—H15B	0.9800
C7—C8	1.5196 (16)	C15—H15C	0.9800
C7—N1—C10	112.13 (10)	C1—C2—H2	120.6
C7—N1—C1	123.44 (10)	C3—C2—H2	120.6
C10—N1—C1	124.24 (9)	C4—C3—H3	119.8
C11—O3—C9	116.83 (10)	C2—C3—H3	119.8
C13—O5—C8	116.70 (10)	C3—C4—H4	119.5
C2—C1—C6	121.35 (11)	C5—C4—H4	119.5
C2—C1—N1	118.97 (10)	C1—C6—H6	120.1
C6—C1—N1	119.66 (11)	C5—C6—H6	120.1
C1—C2—C3	118.78 (11)	O5—C8—H8	110.6
C4—C3—C2	120.35 (12)	C9—C8—H8	110.6
C3—C4—C5	121.02 (11)	C7—C8—H8	110.6
C4—C5—C6	118.67 (10)	O3—C9—H9	109.8
C4—C5—C15	120.03 (11)	C8—C9—H9	109.8
C6—C5—C15	121.31 (11)	C10—C9—H9	109.8
C1—C6—C5	119.80 (11)	C11—C12—H12A	109.5
O1—C7—N1	126.33 (11)	C11—C12—H12B	109.5
O1—C7—C8	125.94 (10)	H12A—C12—H12B	109.5
N1—C7—C8	107.73 (9)	C11—C12—H12C	109.5
O5—C8—C9	110.88 (10)	H12A—C12—H12C	109.5
O5—C8—C7	110.22 (9)	H12B—C12—H12C	109.5
C9—C8—C7	103.69 (9)	C13—C14—H14A	109.5
O3—C9—C8	112.97 (9)	C13—C14—H14B	109.5
O3—C9—C10	110.28 (9)	H14A—C14—H14B	109.5
C8—C9—C10	104.14 (10)	C13—C14—H14C	109.5
O2—C10—N1	126.34 (11)	H14A—C14—H14C	109.5
O2—C10—C9	126.64 (11)	H14B—C14—H14C	109.5
N1—C10—C9	106.95 (9)	C5—C15—H15A	109.5
O4—C11—O3	123.30 (11)	C5—C15—H15B	109.5
O4—C11—C12	127.42 (13)	H15A—C15—H15B	109.5
O3—C11—C12	109.28 (12)	C5—C15—H15C	109.5
O6—C13—O5	122.99 (12)	H15A—C15—H15C	109.5
O6—C13—C14	127.10 (12)	H15B—C15—H15C	109.5
O5—C13—C14	109.91 (11)
C7—N1—C1—C2	−123.73 (13)	N1—C7—C8—O5	137.39 (10)
C10—N1—C1—C2	50.86 (16)	O1—C7—C8—C9	−161.45 (14)
C7—N1—C1—C6	54.68 (16)	N1—C7—C8—C9	18.66 (14)
C10—N1—C1—C6	−130.73 (12)	C11—O3—C9—C8	−121.50 (11)
C6—C1—C2—C3	−1.77 (18)	C11—O3—C9—C10	122.43 (11)
N1—C1—C2—C3	176.61 (10)	O5—C8—C9—O3	99.30 (11)
C1—C2—C3—C4	0.19 (18)	C7—C8—C9—O3	−142.43 (10)
C2—C3—C4—C5	1.31 (18)	O5—C8—C9—C10	−141.03 (9)
C3—C4—C5—C6	−1.23 (17)	C7—C8—C9—C10	−22.76 (12)
C3—C4—C5—C15	178.99 (12)	C7—N1—C10—O2	174.41 (12)
C2—C1—C6—C5	1.85 (18)	C1—N1—C10—O2	−0.7 (2)
N1—C1—C6—C5	−176.52 (11)	C7—N1—C10—C9	−8.51 (14)
C4—C5—C6—C1	−0.33 (17)	C1—N1—C10—C9	176.36 (11)
C15—C5—C6—C1	179.45 (12)	O3—C9—C10—O2	−41.62 (17)
C10—N1—C7—O1	173.58 (14)	C8—C9—C10—O2	−163.10 (12)
C1—N1—C7—O1	−11.3 (2)	O3—C9—C10—N1	141.31 (10)
C10—N1—C7—C8	−6.52 (15)	C8—C9—C10—N1	19.83 (12)
C1—N1—C7—C8	168.64 (11)	C9—O3—C11—O4	−1.53 (16)
C13—O5—C8—C9	−144.04 (10)	C9—O3—C11—C12	179.15 (9)
C13—O5—C8—C7	101.73 (12)	C8—O5—C13—O6	1.85 (18)
O1—C7—C8—O5	−42.72 (18)	C8—O5—C13—C14	−177.72 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O1i	0.98	2.25	3.1957 (17)	161
C15—H15A···O2ii	0.98	2.52	3.4104 (17)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O1i	0.98	2.25	3.1957 (17)	161
C15—H15A⋯O2ii	0.98	2.52	3.4104 (17)	150

Symmetry codes: (i) ; (ii) .