Download citation
Download citation
link to html
The molecule of the title compound, C11H11NO4 (alternative name: 4,5-dimeth­oxy-N-methyl­phthalimide), a highly fluorescent phthal­imide, is essentially planar. In the crystal structure, pairs of mol­ecules form a π-stacked head-to-tail dimer with a remarkably short inter­planar distance of 3.34 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040888/rz2076sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040888/rz2076Isup2.hkl
Contains datablock I

CCDC reference: 628073

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.124
  • Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.90 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL 99 (Keller & Pierrard, 1999); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and enCIFer (Allen et al., 2004).

5,6-Dimethoxy-2-methylisoindole-1,3-dione top
Crystal data top
C11H11NO4Z = 2
Mr = 221.21F(000) = 232
Triclinic, P1Dx = 1.488 Mg m3
Hall symbol: -P 1Melting point: 538 K
a = 7.3142 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.3134 (11) ÅCell parameters from 2663 reflections
c = 9.7468 (16) Åθ = 2.3–27.0°
α = 96.266 (4)°µ = 0.12 mm1
β = 108.402 (6)°T = 100 K
γ = 114.087 (6)°Prism, colourless
V = 493.64 (11) Å30.2 × 0.13 × 0.1 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1404 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.0°, θmin = 2.3°
φ and ω scansh = 99
2663 measured reflectionsk = 107
2073 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.1764P]
where P = (Fo2 + 2Fc2)/3
2073 reflections(Δ/σ)max = 0.001
189 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
xyzUiso*/Ueq
O10.3600 (3)0.7240 (2)0.65825 (19)0.0220 (4)
O20.6696 (3)1.3477 (2)0.83423 (19)0.0207 (4)
O31.1094 (2)1.1852 (2)1.33103 (18)0.0179 (4)
O40.9420 (2)0.8394 (2)1.23234 (18)0.0179 (4)
N10.4832 (3)1.0381 (3)0.7118 (2)0.0163 (5)
C10.4784 (4)0.8761 (3)0.7434 (3)0.0163 (5)
C20.6352 (4)1.1911 (3)0.8328 (3)0.0148 (5)
C30.7377 (3)1.1215 (3)0.9533 (3)0.0139 (5)
C40.8961 (4)1.2165 (3)1.0968 (3)0.0143 (5)
C50.9580 (3)1.1142 (3)1.1872 (3)0.0151 (5)
C60.8639 (4)0.9214 (3)1.1325 (3)0.0141 (5)
C70.7056 (4)0.8294 (3)0.9877 (3)0.0141 (5)
C80.6437 (3)0.9333 (3)0.8992 (3)0.0137 (5)
C91.1924 (4)1.3765 (3)1.4001 (3)0.0232 (6)
C100.8318 (4)0.6425 (3)1.1922 (3)0.0227 (6)
C110.3379 (4)1.0457 (4)0.5728 (3)0.0212 (6)
H40.964 (3)1.347 (3)1.128 (2)0.010 (6)*
H70.637 (3)0.699 (3)0.946 (3)0.010 (6)*
H9A1.298 (4)1.403 (3)1.507 (3)0.031 (7)*
H9B1.274 (4)1.455 (3)1.344 (3)0.019 (6)*
H9C1.071 (4)1.405 (3)1.394 (3)0.029 (7)*
H10A0.839 (4)0.591 (3)1.097 (3)0.028 (7)*
H10B0.670 (5)0.599 (4)1.179 (3)0.042 (8)*
H10C0.905 (4)0.610 (3)1.283 (3)0.034 (8)*
H11A0.263 (4)0.928 (4)0.495 (3)0.025 (7)*
H11B0.428 (4)1.144 (4)0.538 (3)0.036 (8)*
H11C0.227 (5)1.074 (4)0.595 (3)0.049 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0218 (9)0.0191 (10)0.0162 (10)0.0071 (8)0.0021 (8)0.0009 (8)
O20.0228 (9)0.0194 (10)0.0210 (10)0.0113 (8)0.0065 (8)0.0097 (8)
O30.0208 (9)0.0147 (9)0.0114 (9)0.0079 (7)0.0008 (7)0.0023 (7)
O40.0221 (9)0.0150 (9)0.0159 (9)0.0098 (7)0.0044 (7)0.0065 (7)
N10.0158 (10)0.0203 (11)0.0115 (11)0.0095 (9)0.0023 (9)0.0050 (9)
C10.0148 (12)0.0218 (14)0.0159 (13)0.0104 (11)0.0078 (11)0.0057 (11)
C20.0126 (11)0.0187 (13)0.0149 (13)0.0076 (10)0.0068 (10)0.0066 (10)
C30.0136 (12)0.0189 (13)0.0119 (13)0.0097 (10)0.0051 (10)0.0062 (10)
C40.0157 (12)0.0128 (13)0.0144 (13)0.0067 (10)0.0059 (11)0.0040 (10)
C50.0129 (12)0.0180 (13)0.0127 (13)0.0069 (10)0.0039 (10)0.0024 (10)
C60.0159 (11)0.0180 (13)0.0136 (13)0.0106 (10)0.0068 (11)0.0087 (10)
C70.0170 (12)0.0116 (12)0.0144 (13)0.0070 (10)0.0069 (11)0.0032 (10)
C80.0128 (11)0.0169 (13)0.0118 (13)0.0074 (10)0.0052 (10)0.0030 (10)
C90.0263 (15)0.0134 (14)0.0185 (15)0.0061 (11)0.0007 (13)0.0007 (11)
C100.0300 (15)0.0159 (14)0.0222 (16)0.0119 (12)0.0075 (13)0.0088 (12)
C110.0216 (13)0.0317 (16)0.0108 (14)0.0158 (13)0.0015 (11)0.0088 (12)
Geometric parameters (Å, º) top
O1—C11.209 (3)C4—H40.95 (2)
O2—C21.218 (3)C5—C61.417 (3)
O3—C51.358 (3)C6—C71.388 (3)
O3—C91.439 (3)C7—C81.389 (3)
O4—C61.360 (3)C7—H70.96 (2)
O4—C101.437 (3)C9—H9A1.01 (3)
N1—C21.391 (3)C9—H9B1.03 (3)
N1—C11.403 (3)C9—H9C0.99 (2)
N1—C111.461 (3)C10—H10A1.01 (3)
C1—C81.485 (3)C10—H10B1.04 (3)
C2—C31.491 (3)C10—H10C1.00 (3)
C3—C41.382 (3)C11—H11A0.99 (3)
C3—C81.383 (3)C11—H11B0.99 (3)
C4—C51.390 (3)C11—H11C1.01 (3)
C5—O3—C9117.38 (18)C6—C7—H7124.0 (13)
C6—O4—C10117.26 (19)C8—C7—H7118.5 (13)
C2—N1—C1111.78 (19)C3—C8—C7121.1 (2)
C2—N1—C11123.6 (2)C3—C8—C1108.53 (19)
C1—N1—C11124.5 (2)C7—C8—C1130.4 (2)
O1—C1—N1125.3 (2)O3—C9—H9A105.9 (15)
O1—C1—C8129.1 (2)O3—C9—H9B110.2 (13)
N1—C1—C8105.66 (19)H9A—C9—H9B109 (2)
O2—C2—N1124.6 (2)O3—C9—H9C110.6 (15)
O2—C2—C3129.2 (2)H9A—C9—H9C114 (2)
N1—C2—C3106.12 (19)H9B—C9—H9C106 (2)
C4—C3—C8122.5 (2)O4—C10—H10A110.1 (15)
C4—C3—C2129.6 (2)O4—C10—H10B108.2 (15)
C8—C3—C2107.9 (2)H10A—C10—H10B111 (2)
C3—C4—C5117.1 (2)O4—C10—H10C104.9 (15)
C3—C4—H4119.9 (13)H10A—C10—H10C115 (2)
C5—C4—H4122.9 (13)H10B—C10—H10C108 (2)
O3—C5—C4124.7 (2)N1—C11—H11A110.5 (15)
O3—C5—C6114.38 (19)N1—C11—H11B107.7 (16)
C4—C5—C6120.9 (2)H11A—C11—H11B110 (2)
O4—C6—C7124.6 (2)N1—C11—H11C108.4 (17)
O4—C6—C5114.6 (2)H11A—C11—H11C110 (2)
C7—C6—C5120.9 (2)H11B—C11—H11C111 (2)
C6—C7—C8117.6 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds