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The title compound, C
29H
18N
2O
4, 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
CCDC reference: 657703
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (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
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.
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).
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.
N,
N'-(Methylenedi-
p-phenylene)diphthalimide
top
Crystal data top
C29H18N2O4 | F(000) = 476 |
Mr = 458.45 | Dx = 1.394 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 1420 reflections |
a = 31.669 (6) Å | θ = 2.6–23.9° |
b = 4.913 (1) Å | µ = 0.09 mm−1 |
c = 7.1543 (14) Å | T = 292 K |
β = 101.087 (3)° | Plate, colorless |
V = 1092.4 (4) Å3 | 0.30 × 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 tube | Rint = 0.099 |
Graphite monochromator | θmax = 27.7°, θmin = 1.3° |
φ and ω scans | h = −38→40 |
4646 measured reflections | k = −6→6 |
1414 independent reflections | l = −9→9 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-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 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
Crystal data top
C29H18N2O4 | V = 1092.4 (4) Å3 |
Mr = 458.45 | Z = 2 |
Monoclinic, C2 | Mo Kα radiation |
a = 31.669 (6) Å | µ = 0.09 mm−1 |
b = 4.913 (1) Å | T = 292 K |
c = 7.1543 (14) Å | 0.30 × 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 reflections | Rint = 0.099 |
1414 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 1 restraint |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
1414 reflections | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.0000 | 1.2197 (11) | 0.5000 | 0.0462 (11) | |
H1A | 0.0149 | 1.3359 | 0.4244 | 0.055* | 0.50 |
H1B | −0.0149 | 1.3359 | 0.5756 | 0.055* | 0.50 |
O1 | 0.08076 (7) | 0.4639 (6) | 1.2283 (3) | 0.0545 (6) | |
N1 | 0.12141 (7) | 0.5510 (6) | 0.9965 (3) | 0.0411 (6) | |
C2 | 0.03274 (8) | 1.0474 (6) | 0.6323 (4) | 0.0380 (7) | |
C6 | 0.08665 (9) | 0.6935 (7) | 0.6772 (4) | 0.0430 (8) | |
H6 | 0.1027 | 0.5654 | 0.6253 | 0.052* | |
C7 | 0.09194 (9) | 0.7230 (7) | 0.8729 (4) | 0.0382 (7) | |
C5 | 0.06775 (10) | 0.9128 (7) | 0.9478 (4) | 0.0453 (8) | |
H5 | 0.0711 | 0.9328 | 1.0791 | 0.054* | |
C8 | 0.11301 (9) | 0.4301 (7) | 1.1647 (4) | 0.0411 (7) | |
C3 | 0.03847 (10) | 1.0736 (7) | 0.8271 (4) | 0.0462 (8) | |
H3 | 0.0224 | 1.2017 | 0.8788 | 0.055* | |
C4 | 0.05731 (9) | 0.8558 (7) | 0.5600 (4) | 0.0433 (7) | |
H4 | 0.0540 | 0.8359 | 0.4287 | 0.052* | |
C10 | 0.15041 (9) | 0.2547 (7) | 1.2393 (4) | 0.0436 (7) | |
C9 | 0.16170 (9) | 0.4632 (8) | 0.9611 (4) | 0.0467 (8) | |
C15 | 0.17918 (9) | 0.2712 (7) | 1.1170 (4) | 0.0452 (8) | |
O2 | 0.17754 (7) | 0.5373 (7) | 0.8300 (4) | 0.0663 (8) | |
C13 | 0.22405 (11) | −0.0462 (9) | 1.3047 (5) | 0.0626 (10) | |
H13 | 0.2492 | −0.1487 | 1.3296 | 0.075* | |
C12 | 0.19526 (12) | −0.0669 (10) | 1.4255 (5) | 0.0623 (10) | |
H12 | 0.2009 | −0.1861 | 1.5283 | 0.075* | |
C11 | 0.15807 (11) | 0.0869 (8) | 1.3963 (5) | 0.0538 (9) | |
H11 | 0.1389 | 0.0775 | 1.4796 | 0.065* | |
C14 | 0.21666 (10) | 0.1221 (8) | 1.1479 (5) | 0.0550 (9) | |
H14 | 0.2362 | 0.1344 | 1.0663 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.045 (2) | 0.043 (2) | 0.049 (2) | 0.000 | 0.0044 (19) | 0.000 |
O1 | 0.0553 (12) | 0.0652 (16) | 0.0487 (12) | 0.0067 (13) | 0.0246 (10) | −0.0001 (12) |
N1 | 0.0334 (12) | 0.0523 (16) | 0.0379 (12) | −0.0001 (12) | 0.0081 (9) | −0.0005 (12) |
C2 | 0.0318 (13) | 0.0395 (16) | 0.0429 (15) | −0.0057 (13) | 0.0075 (11) | −0.0021 (13) |
C6 | 0.0377 (15) | 0.051 (2) | 0.0422 (16) | 0.0029 (15) | 0.0117 (12) | −0.0059 (15) |
C7 | 0.0334 (14) | 0.0439 (16) | 0.0377 (14) | −0.0041 (13) | 0.0080 (11) | 0.0002 (14) |
C5 | 0.0512 (17) | 0.049 (2) | 0.0368 (15) | 0.0000 (16) | 0.0102 (12) | −0.0059 (14) |
C8 | 0.0449 (16) | 0.0454 (18) | 0.0343 (14) | −0.0037 (15) | 0.0111 (11) | −0.0040 (13) |
C3 | 0.0482 (17) | 0.0474 (19) | 0.0450 (16) | 0.0025 (15) | 0.0136 (13) | −0.0088 (15) |
C4 | 0.0424 (16) | 0.0526 (19) | 0.0354 (14) | 0.0019 (14) | 0.0085 (12) | −0.0031 (14) |
C10 | 0.0378 (15) | 0.0486 (18) | 0.0425 (16) | −0.0036 (14) | 0.0028 (12) | −0.0029 (14) |
C9 | 0.0327 (14) | 0.060 (2) | 0.0476 (17) | −0.0019 (15) | 0.0086 (12) | 0.0007 (16) |
C15 | 0.0368 (15) | 0.050 (2) | 0.0469 (17) | −0.0035 (14) | 0.0040 (13) | −0.0003 (15) |
O2 | 0.0431 (12) | 0.099 (2) | 0.0623 (14) | 0.0104 (14) | 0.0237 (11) | 0.0237 (15) |
C13 | 0.0462 (18) | 0.065 (2) | 0.072 (2) | 0.0046 (19) | −0.0004 (17) | 0.008 (2) |
C12 | 0.061 (2) | 0.061 (2) | 0.058 (2) | −0.001 (2) | −0.0065 (17) | 0.0114 (19) |
C11 | 0.0558 (19) | 0.062 (2) | 0.0417 (17) | −0.0080 (17) | 0.0043 (14) | 0.0063 (17) |
C14 | 0.0412 (17) | 0.065 (2) | 0.058 (2) | 0.0027 (16) | 0.0072 (15) | 0.0041 (18) |
Geometric parameters (Å, º) top
C1—C2 | 1.520 (4) | C8—C10 | 1.479 (4) |
C1—C2i | 1.520 (4) | C3—H3 | 0.9300 |
C1—H1A | 0.9700 | C4—H4 | 0.9300 |
C1—H1B | 0.9700 | C10—C11 | 1.376 (5) |
O1—C8 | 1.207 (3) | C10—C15 | 1.382 (5) |
N1—C8 | 1.412 (4) | C9—O2 | 1.202 (4) |
N1—C9 | 1.415 (4) | C9—C15 | 1.484 (5) |
N1—C7 | 1.432 (4) | C15—C14 | 1.376 (5) |
C2—C3 | 1.376 (4) | C13—C12 | 1.375 (6) |
C2—C4 | 1.384 (4) | C13—C14 | 1.377 (5) |
C6—C4 | 1.379 (4) | C13—H13 | 0.9300 |
C6—C7 | 1.385 (4) | C12—C11 | 1.381 (5) |
C6—H6 | 0.9300 | C12—H12 | 0.9300 |
C7—C5 | 1.379 (4) | C11—H11 | 0.9300 |
C5—C3 | 1.386 (4) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | | |
| | | |
C2—C1—C2i | 112.3 (4) | C5—C3—H3 | 119.3 |
C2—C1—H1A | 109.1 | C6—C4—C2 | 121.9 (3) |
C2i—C1—H1A | 109.1 | C6—C4—H4 | 119.1 |
C2—C1—H1B | 109.1 | C2—C4—H4 | 119.1 |
C2i—C1—H1B | 109.1 | C11—C10—C15 | 121.2 (3) |
H1A—C1—H1B | 107.9 | C11—C10—C8 | 130.3 (3) |
C8—N1—C9 | 110.4 (3) | C15—C10—C8 | 108.5 (3) |
C8—N1—C7 | 124.6 (2) | O2—C9—N1 | 125.0 (3) |
C9—N1—C7 | 124.9 (3) | O2—C9—C15 | 128.9 (3) |
C3—C2—C4 | 117.9 (3) | N1—C9—C15 | 106.2 (3) |
C3—C2—C1 | 121.3 (3) | C14—C15—C10 | 121.3 (3) |
C4—C2—C1 | 120.8 (3) | C14—C15—C9 | 130.2 (3) |
C4—C6—C7 | 119.4 (3) | C10—C15—C9 | 108.5 (3) |
C4—C6—H6 | 120.3 | C12—C13—C14 | 121.8 (4) |
C7—C6—H6 | 120.3 | C12—C13—H13 | 119.1 |
C5—C7—C6 | 119.7 (3) | C14—C13—H13 | 119.1 |
C5—C7—N1 | 120.2 (3) | C13—C12—C11 | 120.9 (4) |
C6—C7—N1 | 120.0 (3) | C13—C12—H12 | 119.6 |
C7—C5—C3 | 119.9 (3) | C11—C12—H12 | 119.6 |
C7—C5—H5 | 120.1 | C10—C11—C12 | 117.6 (3) |
C3—C5—H5 | 120.1 | C10—C11—H11 | 121.2 |
O1—C8—N1 | 125.1 (3) | C12—C11—H11 | 121.2 |
O1—C8—C10 | 128.4 (3) | C15—C14—C13 | 117.2 (4) |
N1—C8—C10 | 106.5 (3) | C15—C14—H14 | 121.4 |
C2—C3—C5 | 121.3 (3) | C13—C14—H14 | 121.4 |
C2—C3—H3 | 119.3 | | |
| | | |
C2i—C1—C2—C3 | −122.7 (3) | O1—C8—C10—C15 | 177.8 (3) |
C2i—C1—C2—C4 | 56.4 (2) | N1—C8—C10—C15 | −0.7 (3) |
C4—C6—C7—C5 | 0.3 (5) | C8—N1—C9—O2 | −178.4 (4) |
C4—C6—C7—N1 | 178.3 (3) | C7—N1—C9—O2 | 5.5 (5) |
C8—N1—C7—C5 | 40.3 (4) | C8—N1—C9—C15 | 0.9 (4) |
C9—N1—C7—C5 | −144.2 (3) | C7—N1—C9—C15 | −175.2 (3) |
C8—N1—C7—C6 | −137.7 (3) | C11—C10—C15—C14 | −0.4 (5) |
C9—N1—C7—C6 | 37.8 (4) | C8—C10—C15—C14 | −178.1 (3) |
C6—C7—C5—C3 | −0.3 (5) | C11—C10—C15—C9 | 179.0 (3) |
N1—C7—C5—C3 | −178.3 (3) | C8—C10—C15—C9 | 1.2 (4) |
C9—N1—C8—O1 | −178.7 (3) | O2—C9—C15—C14 | −2.8 (7) |
C7—N1—C8—O1 | −2.7 (5) | N1—C9—C15—C14 | 177.9 (3) |
C9—N1—C8—C10 | −0.1 (3) | O2—C9—C15—C10 | 178.0 (4) |
C7—N1—C8—C10 | 175.9 (3) | N1—C9—C15—C10 | −1.3 (4) |
C4—C2—C3—C5 | −0.3 (5) | C14—C13—C12—C11 | −1.6 (6) |
C1—C2—C3—C5 | 178.8 (3) | C15—C10—C11—C12 | −0.9 (5) |
C7—C5—C3—C2 | 0.3 (5) | C8—C10—C11—C12 | 176.3 (4) |
C7—C6—C4—C2 | −0.3 (5) | C13—C12—C11—C10 | 1.8 (6) |
C3—C2—C4—C6 | 0.3 (5) | C10—C15—C14—C13 | 0.6 (5) |
C1—C2—C4—C6 | −178.8 (3) | C9—C15—C14—C13 | −178.5 (3) |
O1—C8—C10—C11 | 0.4 (6) | C12—C13—C14—C15 | 0.4 (6) |
N1—C8—C10—C11 | −178.1 (3) | | |
Symmetry code: (i) −x, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1ii | 0.93 | 2.57 | 3.251 (4) | 131 |
Symmetry code: (ii) x, y, z−1. |
Experimental details
Crystal data |
Chemical formula | C29H18N2O4 |
Mr | 458.45 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 292 |
a, b, c (Å) | 31.669 (6), 4.913 (1), 7.1543 (14) |
β (°) | 101.087 (3) |
V (Å3) | 1092.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART 4K CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4646, 1414, 1161 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.655 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.136, 1.05 |
No. of reflections | 1414 |
No. of parameters | 159 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Selected geometric parameters (Å, º) topC1—C2 | 1.520 (4) | N1—C9 | 1.415 (4) |
O1—C8 | 1.207 (3) | N1—C7 | 1.432 (4) |
N1—C8 | 1.412 (4) | C9—O2 | 1.202 (4) |
| | | |
C8—N1—C9 | 110.4 (3) | O1—C8—N1 | 125.1 (3) |
C8—N1—C7 | 124.6 (2) | O1—C8—C10 | 128.4 (3) |
C9—N1—C7 | 124.9 (3) | O2—C9—N1 | 125.0 (3) |
C5—C7—N1 | 120.2 (3) | N1—C9—C15 | 106.2 (3) |
| | | |
C2i—C1—C2—C3 | −122.7 (3) | C7—N1—C8—C10 | 175.9 (3) |
C2i—C1—C2—C4 | 56.4 (2) | O1—C8—C10—C11 | 0.4 (6) |
C9—N1—C7—C5 | −144.2 (3) | N1—C8—C10—C11 | −178.1 (3) |
C8—N1—C7—C6 | −137.7 (3) | O1—C8—C10—C15 | 177.8 (3) |
C9—N1—C8—O1 | −178.7 (3) | C8—N1—C9—C15 | 0.9 (4) |
C7—N1—C8—O1 | −2.7 (5) | C7—N1—C9—C15 | −175.2 (3) |
C9—N1—C8—C10 | −0.1 (3) | C8—C10—C15—C14 | −178.1 (3) |
Symmetry code: (i) −x, y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1ii | 0.93 | 2.57 | 3.251 (4) | 130.8 |
Symmetry code: (ii) x, y, z−1. |
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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).