Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017333/hb2366sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017333/hb2366Isup2.hkl |
CCDC reference: 647576
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.132
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.33 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N2 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.12 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl4 .. O2 .. 3.24 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of tetrachloroisobenzofuran-1,3-dione (0.01 mol) and urea (0.01 mol) in acetic acid (10 ml) was refluxed for 5 h. After cooling, filtration and drying, the compound tetrachloroisoindoline-1,3-dione was obtained. This compound (10 mg) was dissolved in DMF (5 ml) and the solution was allowed to evaporate at room temperature. Colourless single crystals of (I) were formed after 20 d.
The H atoms were positioned geometrically, with C—H = 0.93–0.96 Å and N—H = 0.86 Å, and refined as riding, with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).
Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities. Phthalimides have also served as starting materials and intermediates for the syntheses of alkaloids. In this paper, the structure of the title compound, (I), is reported.
The asymmetric unit of (I) (Fig. 1) consists one tetrachloroisoindoline-1,3-dione molecule and one DMF solvent molecule. The tetrachloroisoindoline-1,3-dione molecule is essentially planar, with an r.m.s.
deviation of 0.022 (2) Å from the mean plane for the non-H atoms. The DMF molecule is also planar, with an r.m.s. deviation of 0.007 (3) Å for the non-H
atoms (Fig. 2). The dihedral angle between the two molecules is 113.8 (2)°. The
geometric parameters of tetrachloroisoindoline-1,3-dione are similar to those in the compound N-methylphthalimide (Liang & Li, 2006).
The crystal structure of (I) is stabilized by N—H···O, C—H···O and C—H···Cl hydrogen bonds (Fig.2 and Table 1).
For the structure of the related N-methylphthalimide, see Liang & Li (2006).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8HCl4NO2·C3H7NO | Z = 2 |
Mr = 357.99 | F(000) = 360 |
Triclinic, P1 | Dx = 1.675 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6583 (16) Å | Cell parameters from 1410 reflections |
b = 11.268 (3) Å | θ = 3.6–24.8° |
c = 11.817 (3) Å | µ = 0.84 mm−1 |
α = 73.244 (4)° | T = 294 K |
β = 82.518 (5)° | Block, colourless |
γ = 80.991 (5)° | 0.26 × 0.20 × 0.12 mm |
V = 709.6 (3) Å3 |
Bruker SMART CCD area-detector diffractometer | 2488 independent reflections |
Radiation source: fine-focus sealed tube | 1776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −5→6 |
Tmin = 0.811, Tmax = 0.906 | k = −9→13 |
3691 measured reflections | l = −14→13 |
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)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.062P)2 + 0.5593P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2488 reflections | Δρmax = 0.98 e Å−3 |
184 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.031 (4) |
C8HCl4NO2·C3H7NO | γ = 80.991 (5)° |
Mr = 357.99 | V = 709.6 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.6583 (16) Å | Mo Kα radiation |
b = 11.268 (3) Å | µ = 0.84 mm−1 |
c = 11.817 (3) Å | T = 294 K |
α = 73.244 (4)° | 0.26 × 0.20 × 0.12 mm |
β = 82.518 (5)° |
Bruker SMART CCD area-detector diffractometer | 2488 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1776 reflections with I > 2σ(I) |
Tmin = 0.811, Tmax = 0.906 | Rint = 0.025 |
3691 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.98 e Å−3 |
2488 reflections | Δρmin = −0.30 e Å−3 |
184 parameters |
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 | 1.31478 (18) | 0.50354 (9) | 0.38085 (9) | 0.0521 (3) | |
Cl2 | 1.0432 (2) | 0.53339 (11) | 0.15763 (10) | 0.0718 (4) | |
Cl3 | 0.6824 (2) | 0.35207 (11) | 0.16242 (9) | 0.0616 (4) | |
Cl4 | 0.59312 (17) | 0.13136 (9) | 0.38830 (9) | 0.0509 (3) | |
O1 | 1.3399 (6) | 0.3021 (3) | 0.6299 (3) | 0.0657 (8) | |
O2 | 0.8175 (5) | 0.0305 (3) | 0.6327 (2) | 0.0588 (8) | |
N1 | 1.0840 (6) | 0.1529 (3) | 0.6599 (3) | 0.0494 (8) | |
H1 | 1.1143 | 0.1118 | 0.7310 | 0.059* | |
C1 | 1.1895 (7) | 0.2577 (4) | 0.5967 (3) | 0.0458 (9) | |
C2 | 1.0819 (6) | 0.3003 (3) | 0.4800 (3) | 0.0364 (8) | |
C3 | 1.1208 (6) | 0.4000 (3) | 0.3818 (3) | 0.0402 (8) | |
C4 | 0.9965 (7) | 0.4132 (3) | 0.2833 (3) | 0.0431 (9) | |
C5 | 0.8359 (6) | 0.3311 (3) | 0.2847 (3) | 0.0411 (8) | |
C6 | 0.7955 (6) | 0.2318 (3) | 0.3850 (3) | 0.0377 (8) | |
C7 | 0.9221 (6) | 0.2174 (3) | 0.4818 (3) | 0.0352 (8) | |
C8 | 0.9253 (7) | 0.1202 (3) | 0.5982 (3) | 0.0442 (9) | |
O3 | 0.2152 (6) | 1.0015 (3) | 0.8760 (3) | 0.0703 (9) | |
N2 | 0.5006 (6) | 0.8550 (3) | 0.9699 (3) | 0.0575 (9) | |
C9 | 0.4085 (11) | 0.9480 (5) | 0.8766 (5) | 0.0736 (14) | |
H9 | 0.5104 | 0.9702 | 0.8076 | 0.088* | |
C10 | 0.3708 (13) | 0.8099 (6) | 1.0762 (5) | 0.113 (2) | |
H10A | 0.2469 | 0.8740 | 1.0905 | 0.170* | |
H10B | 0.4755 | 0.7853 | 1.1390 | 0.170* | |
H10C | 0.2993 | 0.7390 | 1.0736 | 0.170* | |
C11 | 0.7448 (11) | 0.8044 (6) | 0.9431 (7) | 0.114 (2) | |
H11A | 0.7946 | 0.8409 | 0.8611 | 0.171* | |
H11B | 0.7545 | 0.7155 | 0.9579 | 0.171* | |
H11C | 0.8480 | 0.8231 | 0.9923 | 0.171* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0567 (6) | 0.0435 (6) | 0.0610 (6) | −0.0187 (5) | −0.0079 (5) | −0.0144 (5) |
Cl2 | 0.0916 (9) | 0.0616 (7) | 0.0538 (6) | −0.0304 (6) | −0.0212 (6) | 0.0149 (5) |
Cl3 | 0.0682 (7) | 0.0733 (8) | 0.0461 (6) | −0.0149 (6) | −0.0246 (5) | −0.0093 (5) |
Cl4 | 0.0471 (6) | 0.0533 (6) | 0.0588 (6) | −0.0178 (4) | −0.0076 (4) | −0.0180 (5) |
O1 | 0.076 (2) | 0.070 (2) | 0.0603 (18) | −0.0251 (16) | −0.0292 (15) | −0.0129 (15) |
O2 | 0.0666 (19) | 0.0518 (17) | 0.0534 (17) | −0.0236 (15) | −0.0044 (14) | 0.0008 (13) |
N1 | 0.061 (2) | 0.0493 (19) | 0.0348 (16) | −0.0105 (16) | −0.0143 (15) | −0.0010 (14) |
C1 | 0.050 (2) | 0.044 (2) | 0.045 (2) | −0.0022 (18) | −0.0114 (17) | −0.0134 (18) |
C2 | 0.0383 (19) | 0.0362 (19) | 0.0366 (18) | −0.0049 (15) | −0.0053 (14) | −0.0119 (15) |
C3 | 0.0393 (19) | 0.0371 (19) | 0.046 (2) | −0.0078 (15) | −0.0055 (16) | −0.0126 (16) |
C4 | 0.049 (2) | 0.038 (2) | 0.0397 (19) | −0.0062 (17) | −0.0082 (16) | −0.0039 (16) |
C5 | 0.043 (2) | 0.044 (2) | 0.0376 (19) | −0.0048 (16) | −0.0119 (16) | −0.0098 (16) |
C6 | 0.0347 (18) | 0.0374 (19) | 0.0434 (19) | −0.0056 (15) | −0.0043 (15) | −0.0139 (16) |
C7 | 0.0366 (19) | 0.0325 (18) | 0.0356 (18) | −0.0022 (15) | −0.0041 (14) | −0.0088 (14) |
C8 | 0.048 (2) | 0.039 (2) | 0.043 (2) | −0.0036 (18) | −0.0070 (17) | −0.0070 (17) |
O3 | 0.070 (2) | 0.076 (2) | 0.0573 (19) | 0.0034 (18) | −0.0231 (16) | −0.0056 (16) |
N2 | 0.058 (2) | 0.052 (2) | 0.067 (2) | −0.0059 (17) | −0.0295 (18) | −0.0125 (18) |
C9 | 0.085 (4) | 0.080 (4) | 0.068 (3) | −0.028 (3) | −0.012 (3) | −0.029 (3) |
C10 | 0.147 (6) | 0.119 (5) | 0.082 (4) | −0.084 (5) | −0.019 (4) | −0.001 (4) |
C11 | 0.081 (4) | 0.102 (5) | 0.175 (7) | 0.001 (4) | −0.023 (4) | −0.067 (5) |
Cl1—C3 | 1.719 (4) | C5—C6 | 1.398 (5) |
Cl2—C4 | 1.720 (4) | C6—C7 | 1.385 (5) |
Cl3—C5 | 1.722 (3) | C7—C8 | 1.491 (5) |
Cl4—C6 | 1.721 (4) | O3—C9 | 1.163 (6) |
O1—C1 | 1.208 (5) | N2—C10 | 1.373 (7) |
O2—C8 | 1.205 (5) | N2—C9 | 1.378 (6) |
N1—C8 | 1.379 (5) | N2—C11 | 1.441 (6) |
N1—C1 | 1.380 (5) | C9—H9 | 0.9300 |
N1—H1 | 0.8600 | C10—H10A | 0.9600 |
C1—C2 | 1.500 (5) | C10—H10B | 0.9600 |
C2—C3 | 1.385 (5) | C10—H10C | 0.9600 |
C2—C7 | 1.392 (5) | C11—H11A | 0.9600 |
C3—C4 | 1.397 (5) | C11—H11B | 0.9600 |
C4—C5 | 1.390 (5) | C11—H11C | 0.9600 |
C8—N1—C1 | 113.8 (3) | C2—C7—C8 | 108.2 (3) |
C8—N1—H1 | 123.1 | O2—C8—N1 | 126.2 (3) |
C1—N1—H1 | 123.1 | O2—C8—C7 | 128.6 (3) |
O1—C1—N1 | 126.2 (3) | N1—C8—C7 | 105.2 (3) |
O1—C1—C2 | 128.6 (4) | C10—N2—C9 | 123.8 (5) |
N1—C1—C2 | 105.2 (3) | C10—N2—C11 | 122.8 (5) |
C3—C2—C7 | 121.5 (3) | C9—N2—C11 | 113.3 (5) |
C3—C2—C1 | 130.9 (3) | O3—C9—N2 | 126.1 (5) |
C7—C2—C1 | 107.5 (3) | O3—C9—H9 | 116.9 |
C2—C3—C4 | 117.4 (3) | N2—C9—H9 | 116.9 |
C2—C3—Cl1 | 121.3 (3) | N2—C10—H10A | 109.5 |
C4—C3—Cl1 | 121.2 (3) | N2—C10—H10B | 109.5 |
C5—C4—C3 | 121.3 (3) | H10A—C10—H10B | 109.5 |
C5—C4—Cl2 | 119.3 (3) | N2—C10—H10C | 109.5 |
C3—C4—Cl2 | 119.4 (3) | H10A—C10—H10C | 109.5 |
C4—C5—C6 | 120.7 (3) | H10B—C10—H10C | 109.5 |
C4—C5—Cl3 | 119.9 (3) | N2—C11—H11A | 109.5 |
C6—C5—Cl3 | 119.3 (3) | N2—C11—H11B | 109.5 |
C7—C6—C5 | 117.9 (3) | H11A—C11—H11B | 109.5 |
C7—C6—Cl4 | 121.2 (3) | N2—C11—H11C | 109.5 |
C5—C6—Cl4 | 121.0 (3) | H11A—C11—H11C | 109.5 |
C6—C7—C2 | 121.1 (3) | H11B—C11—H11C | 109.5 |
C6—C7—C8 | 130.7 (3) | ||
C8—N1—C1—O1 | −177.3 (4) | Cl3—C5—C6—C7 | 179.9 (3) |
C8—N1—C1—C2 | 1.4 (4) | C4—C5—C6—Cl4 | 178.9 (3) |
O1—C1—C2—C3 | −1.1 (7) | Cl3—C5—C6—Cl4 | −0.6 (4) |
N1—C1—C2—C3 | −179.7 (3) | C5—C6—C7—C2 | 0.9 (5) |
O1—C1—C2—C7 | 178.2 (4) | Cl4—C6—C7—C2 | −178.6 (3) |
N1—C1—C2—C7 | −0.5 (4) | C5—C6—C7—C8 | −177.7 (3) |
C7—C2—C3—C4 | −1.1 (5) | Cl4—C6—C7—C8 | 2.8 (5) |
C1—C2—C3—C4 | 178.0 (4) | C3—C2—C7—C6 | 0.0 (5) |
C7—C2—C3—Cl1 | 179.0 (3) | C1—C2—C7—C6 | −179.3 (3) |
C1—C2—C3—Cl1 | −1.9 (5) | C3—C2—C7—C8 | 178.9 (3) |
C2—C3—C4—C5 | 1.4 (5) | C1—C2—C7—C8 | −0.5 (4) |
Cl1—C3—C4—C5 | −178.7 (3) | C1—N1—C8—O2 | 177.4 (4) |
C2—C3—C4—Cl2 | −178.5 (3) | C1—N1—C8—C7 | −1.6 (4) |
Cl1—C3—C4—Cl2 | 1.4 (4) | C6—C7—C8—O2 | 1.0 (7) |
C3—C4—C5—C6 | −0.5 (6) | C2—C7—C8—O2 | −177.7 (4) |
Cl2—C4—C5—C6 | 179.4 (3) | C6—C7—C8—N1 | 180.0 (3) |
C3—C4—C5—Cl3 | 178.9 (3) | C2—C7—C8—N1 | 1.2 (4) |
Cl2—C4—C5—Cl3 | −1.2 (5) | C10—N2—C9—O3 | 1.7 (7) |
C4—C5—C6—C7 | −0.6 (5) | C11—N2—C9—O3 | 178.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.90 | 2.752 (4) | 170 |
C9—H9···O2ii | 0.93 | 2.53 | 3.452 (6) | 175 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C8HCl4NO2·C3H7NO |
Mr | 357.99 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 5.6583 (16), 11.268 (3), 11.817 (3) |
α, β, γ (°) | 73.244 (4), 82.518 (5), 80.991 (5) |
V (Å3) | 709.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.84 |
Crystal size (mm) | 0.26 × 0.20 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.811, 0.906 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3691, 2488, 1776 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.132, 1.04 |
No. of reflections | 2488 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.98, −0.30 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 1.90 | 2.752 (4) | 170 |
C9—H9···O2ii | 0.93 | 2.53 | 3.452 (6) | 175 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y+1, z. |
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Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities. Phthalimides have also served as starting materials and intermediates for the syntheses of alkaloids. In this paper, the structure of the title compound, (I), is reported.
The asymmetric unit of (I) (Fig. 1) consists one tetrachloroisoindoline-1,3-dione molecule and one DMF solvent molecule. The tetrachloroisoindoline-1,3-dione molecule is essentially planar, with an r.m.s.
deviation of 0.022 (2) Å from the mean plane for the non-H atoms. The DMF molecule is also planar, with an r.m.s. deviation of 0.007 (3) Å for the non-H
atoms (Fig. 2). The dihedral angle between the two molecules is 113.8 (2)°. The
geometric parameters of tetrachloroisoindoline-1,3-dione are similar to those in the compound N-methylphthalimide (Liang & Li, 2006).
The crystal structure of (I) is stabilized by N—H···O, C—H···O and C—H···Cl hydrogen bonds (Fig.2 and Table 1).