Download citation
Download citation
link to html
The title compound, C29H18N2O4, crystallizes with one half-mol­ecule in the asymmetric unit, the other half being generated by a crystallographic twofold rotation axis passing through the central C atom. The dihedral angle between the planes of the two central benzene rings is 67.7 (4)°. The terminal isoindole group is approximately planar and makes a dihedral angle of 39.20 (17)° with the attached benzene ring. Inter­molecular C—H...O hydrogen bonds contribute to the stability of the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031698/wk2067sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031698/wk2067Isup2.hkl
Contains datablock I

CCDC reference: 657703

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.135
  • Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. C8 .. 3.17 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.74 From the CIF: _reflns_number_total 1414 Count of symmetry unique reflns 1441 Completeness (_total/calc) 98.13% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Bisimides are heterocyclic compounds, of which some have biological activivity. Moreover, they are synthetic precursor with application in organic synthesis, supramolecular chemistry, polymer synthesis, and for the development new materials and molecular electronic devices (Guzmán-Lucero et al., 2006).

The molecule of the title, (I) is shown in Fig. 1. The compound crystallizes with one half-molecule in the asymmetric unit, the other half being generated by a crystallographic twofold rotation axis passing through the central C atom. There are no signicant different between the bonds and angles of the two molecules. The dihedral angle between the planes of the two central benzene rings is 67.7 (4)°. The terminal isoindole group is approximately planar and makes adihedral angle of 39.20 (17)° with the attached benzene ring.

Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).

Related literature top

For related literature, see: Diego et al. (2006); James (1988).

Experimental top

A solution of phthaloyl dichoride (420, 2 mmol) was added slowly over a period of 10 min to a solution of 4-(4-aminobenzyl)benzenamine (240 mg, 2 mmol) in dichloromethane (20 ml) at 273 K with light yellow solid precipitated. Triethylamine (5 ml) was then added, while the pecipitated light yellow solid was dissolved. After being stirred for 10 hr,the reacted solution became yellow suspension.The compound was purified by filtration with suction and dried (I) (yield 410 mg, 29.14%). Single crystals of (I) were obtained by recrystallization from DMF at room temperature.

Refinement top

All H atoms were initially located in a difference Fourier map and then included with constrained bond lengths and isotropic displacement parameters: C—H=0.93Å and Uiso(H)=1.5Ueq(C) for methyl, C—H=0.97Å and Uiso(H)=1.2Ueq(C) for methylene.

Structure description top

Bisimides are heterocyclic compounds, of which some have biological activivity. Moreover, they are synthetic precursor with application in organic synthesis, supramolecular chemistry, polymer synthesis, and for the development new materials and molecular electronic devices (Guzmán-Lucero et al., 2006).

The molecule of the title, (I) is shown in Fig. 1. The compound crystallizes with one half-molecule in the asymmetric unit, the other half being generated by a crystallographic twofold rotation axis passing through the central C atom. There are no signicant different between the bonds and angles of the two molecules. The dihedral angle between the planes of the two central benzene rings is 67.7 (4)°. The terminal isoindole group is approximately planar and makes adihedral angle of 39.20 (17)° with the attached benzene ring.

Intermolecular C—H···O hydrogen bonds contribute to the stability of the structure (Table 1).

For related literature, see: Diego et al. (2006); James (1988).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).
N,N'-(Methylenedi-p-phenylene)diphthalimide top
Crystal data top
C29H18N2O4F(000) = 476
Mr = 458.45Dx = 1.394 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 1420 reflections
a = 31.669 (6) Åθ = 2.6–23.9°
b = 4.913 (1) ŵ = 0.09 mm1
c = 7.1543 (14) ÅT = 292 K
β = 101.087 (3)°Plate, colorless
V = 1092.4 (4) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
1161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.099
Graphite monochromatorθmax = 27.7°, θmin = 1.3°
φ and ω scansh = 3840
4646 measured reflectionsk = 66
1414 independent reflectionsl = 99
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.0873P]
where P = (Fo2 + 2Fc2)/3
1414 reflections(Δ/σ)max = 0.002
159 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.20 e Å3
Crystal data top
C29H18N2O4V = 1092.4 (4) Å3
Mr = 458.45Z = 2
Monoclinic, C2Mo Kα radiation
a = 31.669 (6) ŵ = 0.09 mm1
b = 4.913 (1) ÅT = 292 K
c = 7.1543 (14) Å0.30 × 0.20 × 0.20 mm
β = 101.087 (3)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
1161 reflections with I > 2σ(I)
4646 measured reflectionsRint = 0.099
1414 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.136H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
1414 reflectionsΔρmin = 0.20 e Å3
159 parameters
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*/UeqOcc. (<1)
C10.00001.2197 (11)0.50000.0462 (11)
H1A0.01491.33590.42440.055*0.50
H1B0.01491.33590.57560.055*0.50
O10.08076 (7)0.4639 (6)1.2283 (3)0.0545 (6)
N10.12141 (7)0.5510 (6)0.9965 (3)0.0411 (6)
C20.03274 (8)1.0474 (6)0.6323 (4)0.0380 (7)
C60.08665 (9)0.6935 (7)0.6772 (4)0.0430 (8)
H60.10270.56540.62530.052*
C70.09194 (9)0.7230 (7)0.8729 (4)0.0382 (7)
C50.06775 (10)0.9128 (7)0.9478 (4)0.0453 (8)
H50.07110.93281.07910.054*
C80.11301 (9)0.4301 (7)1.1647 (4)0.0411 (7)
C30.03847 (10)1.0736 (7)0.8271 (4)0.0462 (8)
H30.02241.20170.87880.055*
C40.05731 (9)0.8558 (7)0.5600 (4)0.0433 (7)
H40.05400.83590.42870.052*
C100.15041 (9)0.2547 (7)1.2393 (4)0.0436 (7)
C90.16170 (9)0.4632 (8)0.9611 (4)0.0467 (8)
C150.17918 (9)0.2712 (7)1.1170 (4)0.0452 (8)
O20.17754 (7)0.5373 (7)0.8300 (4)0.0663 (8)
C130.22405 (11)0.0462 (9)1.3047 (5)0.0626 (10)
H130.24920.14871.32960.075*
C120.19526 (12)0.0669 (10)1.4255 (5)0.0623 (10)
H120.20090.18611.52830.075*
C110.15807 (11)0.0869 (8)1.3963 (5)0.0538 (9)
H110.13890.07751.47960.065*
C140.21666 (10)0.1221 (8)1.1479 (5)0.0550 (9)
H140.23620.13441.06630.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.043 (2)0.049 (2)0.0000.0044 (19)0.000
O10.0553 (12)0.0652 (16)0.0487 (12)0.0067 (13)0.0246 (10)0.0001 (12)
N10.0334 (12)0.0523 (16)0.0379 (12)0.0001 (12)0.0081 (9)0.0005 (12)
C20.0318 (13)0.0395 (16)0.0429 (15)0.0057 (13)0.0075 (11)0.0021 (13)
C60.0377 (15)0.051 (2)0.0422 (16)0.0029 (15)0.0117 (12)0.0059 (15)
C70.0334 (14)0.0439 (16)0.0377 (14)0.0041 (13)0.0080 (11)0.0002 (14)
C50.0512 (17)0.049 (2)0.0368 (15)0.0000 (16)0.0102 (12)0.0059 (14)
C80.0449 (16)0.0454 (18)0.0343 (14)0.0037 (15)0.0111 (11)0.0040 (13)
C30.0482 (17)0.0474 (19)0.0450 (16)0.0025 (15)0.0136 (13)0.0088 (15)
C40.0424 (16)0.0526 (19)0.0354 (14)0.0019 (14)0.0085 (12)0.0031 (14)
C100.0378 (15)0.0486 (18)0.0425 (16)0.0036 (14)0.0028 (12)0.0029 (14)
C90.0327 (14)0.060 (2)0.0476 (17)0.0019 (15)0.0086 (12)0.0007 (16)
C150.0368 (15)0.050 (2)0.0469 (17)0.0035 (14)0.0040 (13)0.0003 (15)
O20.0431 (12)0.099 (2)0.0623 (14)0.0104 (14)0.0237 (11)0.0237 (15)
C130.0462 (18)0.065 (2)0.072 (2)0.0046 (19)0.0004 (17)0.008 (2)
C120.061 (2)0.061 (2)0.058 (2)0.001 (2)0.0065 (17)0.0114 (19)
C110.0558 (19)0.062 (2)0.0417 (17)0.0080 (17)0.0043 (14)0.0063 (17)
C140.0412 (17)0.065 (2)0.058 (2)0.0027 (16)0.0072 (15)0.0041 (18)
Geometric parameters (Å, º) top
C1—C21.520 (4)C8—C101.479 (4)
C1—C2i1.520 (4)C3—H30.9300
C1—H1A0.9700C4—H40.9300
C1—H1B0.9700C10—C111.376 (5)
O1—C81.207 (3)C10—C151.382 (5)
N1—C81.412 (4)C9—O21.202 (4)
N1—C91.415 (4)C9—C151.484 (5)
N1—C71.432 (4)C15—C141.376 (5)
C2—C31.376 (4)C13—C121.375 (6)
C2—C41.384 (4)C13—C141.377 (5)
C6—C41.379 (4)C13—H130.9300
C6—C71.385 (4)C12—C111.381 (5)
C6—H60.9300C12—H120.9300
C7—C51.379 (4)C11—H110.9300
C5—C31.386 (4)C14—H140.9300
C5—H50.9300
C2—C1—C2i112.3 (4)C5—C3—H3119.3
C2—C1—H1A109.1C6—C4—C2121.9 (3)
C2i—C1—H1A109.1C6—C4—H4119.1
C2—C1—H1B109.1C2—C4—H4119.1
C2i—C1—H1B109.1C11—C10—C15121.2 (3)
H1A—C1—H1B107.9C11—C10—C8130.3 (3)
C8—N1—C9110.4 (3)C15—C10—C8108.5 (3)
C8—N1—C7124.6 (2)O2—C9—N1125.0 (3)
C9—N1—C7124.9 (3)O2—C9—C15128.9 (3)
C3—C2—C4117.9 (3)N1—C9—C15106.2 (3)
C3—C2—C1121.3 (3)C14—C15—C10121.3 (3)
C4—C2—C1120.8 (3)C14—C15—C9130.2 (3)
C4—C6—C7119.4 (3)C10—C15—C9108.5 (3)
C4—C6—H6120.3C12—C13—C14121.8 (4)
C7—C6—H6120.3C12—C13—H13119.1
C5—C7—C6119.7 (3)C14—C13—H13119.1
C5—C7—N1120.2 (3)C13—C12—C11120.9 (4)
C6—C7—N1120.0 (3)C13—C12—H12119.6
C7—C5—C3119.9 (3)C11—C12—H12119.6
C7—C5—H5120.1C10—C11—C12117.6 (3)
C3—C5—H5120.1C10—C11—H11121.2
O1—C8—N1125.1 (3)C12—C11—H11121.2
O1—C8—C10128.4 (3)C15—C14—C13117.2 (4)
N1—C8—C10106.5 (3)C15—C14—H14121.4
C2—C3—C5121.3 (3)C13—C14—H14121.4
C2—C3—H3119.3
C2i—C1—C2—C3122.7 (3)O1—C8—C10—C15177.8 (3)
C2i—C1—C2—C456.4 (2)N1—C8—C10—C150.7 (3)
C4—C6—C7—C50.3 (5)C8—N1—C9—O2178.4 (4)
C4—C6—C7—N1178.3 (3)C7—N1—C9—O25.5 (5)
C8—N1—C7—C540.3 (4)C8—N1—C9—C150.9 (4)
C9—N1—C7—C5144.2 (3)C7—N1—C9—C15175.2 (3)
C8—N1—C7—C6137.7 (3)C11—C10—C15—C140.4 (5)
C9—N1—C7—C637.8 (4)C8—C10—C15—C14178.1 (3)
C6—C7—C5—C30.3 (5)C11—C10—C15—C9179.0 (3)
N1—C7—C5—C3178.3 (3)C8—C10—C15—C91.2 (4)
C9—N1—C8—O1178.7 (3)O2—C9—C15—C142.8 (7)
C7—N1—C8—O12.7 (5)N1—C9—C15—C14177.9 (3)
C9—N1—C8—C100.1 (3)O2—C9—C15—C10178.0 (4)
C7—N1—C8—C10175.9 (3)N1—C9—C15—C101.3 (4)
C4—C2—C3—C50.3 (5)C14—C13—C12—C111.6 (6)
C1—C2—C3—C5178.8 (3)C15—C10—C11—C120.9 (5)
C7—C5—C3—C20.3 (5)C8—C10—C11—C12176.3 (4)
C7—C6—C4—C20.3 (5)C13—C12—C11—C101.8 (6)
C3—C2—C4—C60.3 (5)C10—C15—C14—C130.6 (5)
C1—C2—C4—C6178.8 (3)C9—C15—C14—C13178.5 (3)
O1—C8—C10—C110.4 (6)C12—C13—C14—C150.4 (6)
N1—C8—C10—C11178.1 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1ii0.932.573.251 (4)131
Symmetry code: (ii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC29H18N2O4
Mr458.45
Crystal system, space groupMonoclinic, C2
Temperature (K)292
a, b, c (Å)31.669 (6), 4.913 (1), 7.1543 (14)
β (°) 101.087 (3)
V3)1092.4 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 4K CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4646, 1414, 1161
Rint0.099
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.136, 1.05
No. of reflections1414
No. of parameters159
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Selected geometric parameters (Å, º) top
C1—C21.520 (4)N1—C91.415 (4)
O1—C81.207 (3)N1—C71.432 (4)
N1—C81.412 (4)C9—O21.202 (4)
C8—N1—C9110.4 (3)O1—C8—N1125.1 (3)
C8—N1—C7124.6 (2)O1—C8—C10128.4 (3)
C9—N1—C7124.9 (3)O2—C9—N1125.0 (3)
C5—C7—N1120.2 (3)N1—C9—C15106.2 (3)
C2i—C1—C2—C3122.7 (3)C7—N1—C8—C10175.9 (3)
C2i—C1—C2—C456.4 (2)O1—C8—C10—C110.4 (6)
C9—N1—C7—C5144.2 (3)N1—C8—C10—C11178.1 (3)
C8—N1—C7—C6137.7 (3)O1—C8—C10—C15177.8 (3)
C9—N1—C8—O1178.7 (3)C8—N1—C9—C150.9 (4)
C7—N1—C8—O12.7 (5)C7—N1—C9—C15175.2 (3)
C9—N1—C8—C100.1 (3)C8—C10—C15—C14178.1 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1ii0.932.573.251 (4)130.8
Symmetry code: (ii) x, y, z1.
 

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