Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050738/bv2068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050738/bv2068Isup2.hkl |
CCDC reference: 608029
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.124
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 3 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
Under N2 atmosphere, cold water bath and stirring, phthalimide (8.8 g) was dissolved in concentrated sulfuric acid (50 ml) followed by the careful addition polyformaldehyde (0.5 g). After the solid disappeared, the solution was warmed to 323 K and stirred for 10 h, then cooled to room temperature, and poured into ice-water with vigorous stirring. The filter cake was washed to be neutral and then dried. The product was purified by chromatography on a silica gel column with alcohol-hexane (V/V=3/7) as eluent. Single crystals of (I) were obtained by slow evaporation from its dichloroethene solution at room temperature.
IR(KBr, ν, cm-1): 3115,3025 (Ar—H), 2968 (C—H), 1731(C=O), 1710 (C=O),1464, 1431, 950, 734. 1H NMR (CDCl3, δ, p.p.m.): 7.860–7.877 (m, 4H), 7.721–7.738(m, 4H), 5.459 (s, 2H).
The H atoms were located in an electron-density difference map and refined isotropically.
N-substituted phthalimides possess important biological activity (Orzeszko et al., 2000). The title compound (I) featuring two phthlimide moieties was synthesized by the reaction of phthalimide with polyformaldehyde in concentrated sulfuric acid. The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the two phthalimides planes is 91.876°. In the crystal structure of (I), the molecules pack in columns through π-π interactions between the phthalimide moieties with distances of 3.470 (1) Å and 3.626 (7) Å, and slip distances of 1.47 Å and 1.62 Å, respectivly. There are weak C—H···O interactions between these columns (Table 1).
For related literature, see: Orzeszko et al. (2000).
Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick,1997).
Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C17H10N2O4 | Z = 2 |
Mr = 306.27 | F(000) = 316 |
Triclinic, P1 | Dx = 1.428 Mg m−3 |
Hall symbol: -P 1 | Melting point = 501.6–502.1 K |
a = 7.6660 (9) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.5810 (8) Å | Cell parameters from 2784 reflections |
c = 10.2780 (6) Å | θ = 5.2–54.6° |
α = 104.325 (3)° | µ = 0.10 mm−1 |
β = 99.768 (4)° | T = 298 K |
γ = 96.030 (3)° | Prism, colourless |
V = 712.23 (11) Å3 | 0.80 × 0.21 × 0.21 mm |
Rigaku R-AXIS RAPID imaging plate system diffractometer | 2604 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode generator | Rint = 0.026 |
Graphite Monochromator monochromator | θmax = 27.5°, θmin = 2.2° |
Detector resolution: 14.6306 pixels mm-1 | h = −9→9 |
ω scans | k = 0→12 |
6295 measured reflections | l = −13→12 |
3181 independent reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.1105P] where P = (Fo2 + 2Fc2)/3 |
3181 reflections | (Δ/σ)max = 0.003 |
248 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C17H10N2O4 | γ = 96.030 (3)° |
Mr = 306.27 | V = 712.23 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6660 (9) Å | Mo Kα radiation |
b = 9.5810 (8) Å | µ = 0.10 mm−1 |
c = 10.2780 (6) Å | T = 298 K |
α = 104.325 (3)° | 0.80 × 0.21 × 0.21 mm |
β = 99.768 (4)° |
Rigaku R-AXIS RAPID imaging plate system diffractometer | 2604 reflections with I > 2σ(I) |
6295 measured reflections | Rint = 0.026 |
3181 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.124 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.14 e Å−3 |
3181 reflections | Δρmin = −0.24 e Å−3 |
248 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 | ||
N1 | 0.22177 (16) | 0.16328 (12) | 0.73250 (11) | 0.0486 (3) | |
N2 | 0.11889 (15) | 0.29986 (12) | 0.57720 (11) | 0.0485 (3) | |
O1 | 0.2051 (2) | 0.28638 (15) | 0.95249 (12) | 0.0804 (4) | |
O2 | 0.30930 (14) | 0.01722 (12) | 0.54975 (9) | 0.0583 (3) | |
O3 | 0.02017 (17) | 0.14751 (12) | 0.35746 (11) | 0.0655 (3) | |
O4 | 0.24441 (19) | 0.49922 (13) | 0.75855 (12) | 0.0765 (4) | |
H1 | 0.557 (3) | 0.256 (2) | 1.104 (2) | 0.084 (6)* | |
H2 | 0.833 (3) | 0.151 (2) | 1.097 (2) | 0.104 (7)* | |
H3 | 0.877 (3) | 0.000 (2) | 0.896 (2) | 0.091 (6)* | |
H4 | 0.662 (2) | −0.039 (2) | 0.683 (2) | 0.073 (5)* | |
H5 | −0.011 (2) | 0.1138 (17) | 0.5916 (16) | 0.056 (4)* | |
H6 | 0.001 (2) | 0.2565 (16) | 0.7257 (16) | 0.051 (4)* | |
H7 | 0.374 (3) | 0.715 (2) | 0.615 (2) | 0.089 (6)* | |
H8 | 0.395 (3) | 0.753 (2) | 0.400 (2) | 0.091 (6)* | |
H9 | 0.300 (3) | 0.573 (2) | 0.198 (2) | 0.088 (6)* | |
H10 | 0.153 (3) | 0.339 (2) | 0.191 (2) | 0.085 (6)* | |
C1 | 0.4607 (2) | 0.16588 (16) | 0.90265 (14) | 0.0541 (4) | |
C2 | 0.5866 (3) | 0.1948 (2) | 1.02293 (17) | 0.0709 (5) | |
C3 | 0.7425 (3) | 0.1341 (2) | 1.0166 (2) | 0.0809 (6) | |
C4 | 0.7714 (3) | 0.0484 (2) | 0.8956 (2) | 0.0766 (5) | |
C5 | 0.6438 (2) | 0.0193 (2) | 0.77442 (17) | 0.0626 (4) | |
C6 | 0.49014 (19) | 0.08017 (15) | 0.78128 (13) | 0.0497 (3) | |
C7 | 0.2845 (2) | 0.21708 (16) | 0.87470 (14) | 0.0559 (4) | |
C8 | 0.33557 (18) | 0.07717 (14) | 0.67038 (13) | 0.0465 (3) | |
C9 | 0.0657 (2) | 0.20282 (16) | 0.65709 (15) | 0.0508 (3) | |
C10 | 0.09578 (19) | 0.26223 (15) | 0.43474 (14) | 0.0495 (3) | |
C11 | 0.2083 (2) | 0.44257 (15) | 0.63763 (15) | 0.0522 (3) | |
C12 | 0.24512 (19) | 0.50100 (15) | 0.52299 (15) | 0.0520 (3) | |
C13 | 0.18072 (19) | 0.39313 (16) | 0.40180 (15) | 0.0512 (3) | |
C14 | 0.1987 (2) | 0.4151 (2) | 0.27754 (18) | 0.0660 (4) | |
C15 | 0.2840 (3) | 0.5515 (2) | 0.2794 (2) | 0.0780 (5) | |
C16 | 0.3456 (3) | 0.6596 (2) | 0.4003 (2) | 0.0762 (5) | |
C17 | 0.3282 (2) | 0.63641 (18) | 0.5248 (2) | 0.0666 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0567 (6) | 0.0478 (6) | 0.0386 (5) | 0.0036 (5) | 0.0095 (5) | 0.0085 (5) |
N2 | 0.0555 (6) | 0.0429 (6) | 0.0433 (6) | 0.0021 (5) | 0.0080 (5) | 0.0086 (5) |
O1 | 0.1052 (10) | 0.0882 (9) | 0.0477 (6) | 0.0289 (8) | 0.0253 (6) | 0.0058 (6) |
O2 | 0.0602 (6) | 0.0692 (7) | 0.0375 (5) | 0.0045 (5) | 0.0081 (4) | 0.0030 (4) |
O3 | 0.0829 (8) | 0.0533 (6) | 0.0487 (6) | −0.0064 (5) | 0.0062 (5) | 0.0048 (5) |
O4 | 0.1027 (10) | 0.0600 (7) | 0.0521 (6) | −0.0079 (6) | 0.0126 (6) | −0.0015 (5) |
C1 | 0.0666 (9) | 0.0507 (8) | 0.0398 (6) | −0.0039 (6) | 0.0053 (6) | 0.0116 (5) |
C2 | 0.0866 (12) | 0.0694 (11) | 0.0434 (8) | −0.0049 (9) | −0.0025 (8) | 0.0085 (7) |
C3 | 0.0744 (12) | 0.0933 (14) | 0.0611 (10) | −0.0078 (10) | −0.0166 (9) | 0.0241 (10) |
C4 | 0.0614 (10) | 0.0969 (14) | 0.0711 (11) | 0.0071 (9) | 0.0022 (9) | 0.0315 (10) |
C5 | 0.0600 (9) | 0.0741 (10) | 0.0542 (9) | 0.0072 (7) | 0.0099 (7) | 0.0210 (8) |
C6 | 0.0543 (7) | 0.0512 (7) | 0.0410 (7) | −0.0017 (6) | 0.0075 (6) | 0.0136 (5) |
C7 | 0.0742 (10) | 0.0518 (8) | 0.0384 (7) | 0.0030 (7) | 0.0134 (7) | 0.0078 (6) |
C8 | 0.0519 (7) | 0.0458 (7) | 0.0389 (6) | −0.0031 (5) | 0.0102 (6) | 0.0101 (5) |
C9 | 0.0533 (8) | 0.0502 (8) | 0.0485 (7) | 0.0041 (6) | 0.0126 (6) | 0.0129 (6) |
C10 | 0.0516 (7) | 0.0490 (7) | 0.0453 (7) | 0.0057 (6) | 0.0089 (6) | 0.0092 (6) |
C11 | 0.0563 (8) | 0.0433 (7) | 0.0522 (8) | 0.0050 (6) | 0.0093 (6) | 0.0062 (6) |
C12 | 0.0499 (7) | 0.0465 (7) | 0.0599 (8) | 0.0085 (6) | 0.0119 (6) | 0.0142 (6) |
C13 | 0.0498 (7) | 0.0531 (8) | 0.0527 (8) | 0.0089 (6) | 0.0119 (6) | 0.0167 (6) |
C14 | 0.0701 (10) | 0.0752 (11) | 0.0583 (9) | 0.0095 (8) | 0.0183 (8) | 0.0255 (8) |
C15 | 0.0787 (12) | 0.0930 (14) | 0.0835 (13) | 0.0173 (10) | 0.0309 (11) | 0.0513 (12) |
C16 | 0.0712 (11) | 0.0650 (11) | 0.1051 (15) | 0.0064 (8) | 0.0282 (11) | 0.0411 (11) |
C17 | 0.0631 (9) | 0.0516 (9) | 0.0849 (12) | 0.0021 (7) | 0.0155 (9) | 0.0206 (8) |
N1—C8 | 1.3889 (18) | C4—H3 | 0.97 (2) |
N1—C7 | 1.4035 (17) | C5—C6 | 1.373 (2) |
N1—C9 | 1.4496 (19) | C5—H4 | 1.008 (19) |
N2—C10 | 1.3938 (17) | C6—C8 | 1.491 (2) |
N2—C11 | 1.4011 (18) | C9—H5 | 1.001 (16) |
N2—C9 | 1.4549 (18) | C9—H6 | 0.999 (16) |
O1—C7 | 1.1991 (19) | C10—C13 | 1.492 (2) |
O2—C8 | 1.2025 (16) | C11—C12 | 1.479 (2) |
O3—C10 | 1.2053 (17) | C12—C17 | 1.378 (2) |
O4—C11 | 1.1974 (18) | C12—C13 | 1.382 (2) |
C1—C2 | 1.381 (2) | C13—C14 | 1.372 (2) |
C1—C6 | 1.382 (2) | C14—C15 | 1.393 (3) |
C1—C7 | 1.491 (2) | C14—H10 | 0.98 (2) |
C2—C3 | 1.387 (3) | C15—C16 | 1.379 (3) |
C2—H1 | 0.97 (2) | C15—H9 | 0.93 (2) |
C3—C4 | 1.378 (3) | C16—C17 | 1.377 (3) |
C3—H2 | 0.95 (2) | C16—H8 | 0.93 (2) |
C4—C5 | 1.394 (2) | C17—H7 | 1.01 (2) |
C8—N1—C7 | 111.95 (12) | N1—C9—N2 | 110.66 (11) |
C8—N1—C9 | 123.56 (11) | N1—C9—H5 | 110.2 (9) |
C7—N1—C9 | 124.28 (12) | N2—C9—H5 | 107.6 (9) |
C10—N2—C11 | 112.04 (12) | N1—C9—H6 | 107.4 (9) |
C10—N2—C9 | 125.16 (11) | N2—C9—H6 | 108.1 (9) |
C11—N2—C9 | 122.74 (12) | H5—C9—H6 | 112.8 (13) |
C2—C1—C6 | 120.95 (16) | O3—C10—N2 | 125.80 (13) |
C2—C1—C7 | 130.36 (15) | O3—C10—C13 | 128.80 (13) |
C6—C1—C7 | 108.67 (12) | N2—C10—C13 | 105.39 (11) |
C1—C2—C3 | 117.31 (17) | O4—C11—N2 | 124.40 (14) |
C1—C2—H1 | 116.6 (12) | O4—C11—C12 | 129.76 (14) |
C3—C2—H1 | 126.1 (12) | N2—C11—C12 | 105.85 (12) |
C4—C3—C2 | 121.65 (17) | C17—C12—C13 | 121.72 (15) |
C4—C3—H2 | 117.8 (14) | C17—C12—C11 | 129.99 (14) |
C2—C3—H2 | 120.5 (14) | C13—C12—C11 | 108.29 (12) |
C3—C4—C5 | 120.85 (19) | C14—C13—C12 | 121.53 (15) |
C3—C4—H3 | 119.8 (13) | C14—C13—C10 | 130.06 (14) |
C5—C4—H3 | 119.1 (13) | C12—C13—C10 | 108.41 (13) |
C6—C5—C4 | 117.20 (17) | C13—C14—C15 | 116.79 (18) |
C6—C5—H4 | 119.5 (11) | C13—C14—H10 | 121.5 (12) |
C4—C5—H4 | 123.2 (11) | C15—C14—H10 | 121.7 (12) |
C5—C6—C1 | 122.04 (14) | C16—C15—C14 | 121.50 (18) |
C5—C6—C8 | 130.12 (13) | C16—C15—H9 | 117.8 (13) |
C1—C6—C8 | 107.77 (13) | C14—C15—H9 | 120.7 (13) |
O1—C7—N1 | 124.82 (16) | C17—C16—C15 | 121.38 (18) |
O1—C7—C1 | 129.90 (14) | C17—C16—H8 | 117.5 (14) |
N1—C7—C1 | 105.26 (12) | C15—C16—H8 | 121.0 (13) |
O2—C8—N1 | 124.37 (13) | C16—C17—C12 | 117.07 (17) |
O2—C8—C6 | 129.37 (14) | C16—C17—H7 | 122.1 (12) |
N1—C8—C6 | 106.24 (11) | C12—C17—H7 | 120.8 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H10···O1i | 0.98 (2) | 2.49 (2) | 3.273 (2) | 136.3 (16) |
C9—H5···O2ii | 1.001 (16) | 2.508 (16) | 3.4152 (18) | 150.6 (12) |
C5—H4···O2iii | 1.008 (19) | 2.50 (2) | 3.3480 (19) | 141.6 (14) |
C2—H1···O4iv | 0.97 (2) | 2.58 (2) | 3.205 (2) | 121.9 (15) |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C17H10N2O4 |
Mr | 306.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.6660 (9), 9.5810 (8), 10.2780 (6) |
α, β, γ (°) | 104.325 (3), 99.768 (4), 96.030 (3) |
V (Å3) | 712.23 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.80 × 0.21 × 0.21 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID imaging plate system |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6295, 3181, 2604 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.124, 1.05 |
No. of reflections | 3181 |
No. of parameters | 248 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.14, −0.24 |
Computer programs: RAPID-AUTO (Rigaku, 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995), SHELXL97 (Sheldrick,1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H10···O1i | 0.98 (2) | 2.49 (2) | 3.273 (2) | 136.3 (16) |
C9—H5···O2ii | 1.001 (16) | 2.508 (16) | 3.4152 (18) | 150.6 (12) |
C5—H4···O2iii | 1.008 (19) | 2.50 (2) | 3.3480 (19) | 141.6 (14) |
C2—H1···O4iv | 0.97 (2) | 2.58 (2) | 3.205 (2) | 121.9 (15) |
Symmetry codes: (i) x, y, z−1; (ii) −x, −y, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+2. |
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N-substituted phthalimides possess important biological activity (Orzeszko et al., 2000). The title compound (I) featuring two phthlimide moieties was synthesized by the reaction of phthalimide with polyformaldehyde in concentrated sulfuric acid. The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the two phthalimides planes is 91.876°. In the crystal structure of (I), the molecules pack in columns through π-π interactions between the phthalimide moieties with distances of 3.470 (1) Å and 3.626 (7) Å, and slip distances of 1.47 Å and 1.62 Å, respectivly. There are weak C—H···O interactions between these columns (Table 1).