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The title compound, C15H9NO3, was synthesized from phthalic anhydride and 4-amino­benz­aldehyde. The dihedral angle between the planes of the phthal­imide moiety and the benzene ring is 56.22 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804028272/sj6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804028272/sj6020Isup2.hkl
Contains datablock I

CCDC reference: 259567

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.091
  • Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.13 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.29 From the CIF: _reflns_number_total 1227 Count of symmetry unique reflns 1235 Completeness (_total/calc) 99.35% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

4-(1,3-dioxoisoindolin-2-yl)benzaldehyde top
Crystal data top
C15H9NO3Dx = 1.427 Mg m3
Mr = 251.23Melting point = 200–201 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2c -2nCell parameters from 1004 reflections
a = 7.646 (3) Åθ = 2.4–24.1°
b = 11.070 (4) ŵ = 0.10 mm1
c = 13.815 (4) ÅT = 293 K
V = 1169.3 (7) Å3Block, colorless
Z = 40.20 × 0.18 × 0.14 mm
F(000) = 520
Data collection top
Bruker SMART CCD area-detector
diffractometer
1227 independent reflections
Radiation source: fine-focus sealed tube947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 26.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.960, Tmax = 0.986k = 1113
6256 measured reflectionsl = 1716
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1003P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.16 e Å3
1227 reflectionsΔρmin = 0.20 e Å3
172 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*/Ueq
O10.1196 (3)1.06929 (19)0.26993 (16)0.0580 (6)
O20.3641 (3)0.69214 (19)0.27035 (16)0.0571 (6)
N10.2437 (3)0.8811 (2)0.29607 (17)0.0383 (6)
C10.1770 (4)0.9753 (3)0.2392 (2)0.0409 (7)
C20.1926 (4)0.9325 (3)0.1376 (2)0.0397 (7)
C30.1478 (4)0.9891 (3)0.0519 (3)0.0495 (8)
H30.09461.06460.05160.059*
C40.1856 (4)0.9286 (4)0.0339 (2)0.0566 (10)
H40.15840.96470.09280.068*
C50.2622 (5)0.8166 (4)0.0331 (2)0.0569 (9)
H50.28550.77780.09140.068*
C60.3059 (4)0.7599 (3)0.0538 (3)0.0498 (7)
H60.35820.68400.05470.060*
C70.2685 (3)0.8202 (3)0.1378 (2)0.0376 (7)
C80.3002 (4)0.7840 (3)0.2400 (2)0.0391 (7)
C90.2575 (4)0.8826 (3)0.3991 (2)0.0360 (7)
C100.1847 (4)0.7895 (3)0.4527 (2)0.0438 (8)
H100.12320.72770.42240.053*
C110.2052 (4)0.7904 (3)0.5522 (2)0.0471 (7)
H110.15600.72880.58900.056*
C120.2976 (4)0.8812 (3)0.5975 (2)0.0426 (8)
C130.3681 (4)0.9737 (3)0.5428 (2)0.0472 (8)
H130.42901.03580.57320.057*
C140.3487 (4)0.9746 (3)0.4437 (2)0.0447 (8)
H140.39671.03680.40710.054*
C150.3234 (5)0.8756 (4)0.7035 (3)0.0663 (11)
H150.26020.81840.73820.080*
O30.4206 (4)0.9404 (3)0.74705 (19)0.1001 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0761 (15)0.0475 (12)0.0503 (13)0.0158 (11)0.0011 (12)0.0029 (12)
O20.0729 (15)0.0539 (13)0.0447 (13)0.0225 (11)0.0049 (11)0.0009 (12)
N10.0392 (15)0.0436 (14)0.0320 (14)0.0042 (11)0.0019 (10)0.0024 (12)
C10.0393 (16)0.0412 (17)0.0423 (19)0.0017 (13)0.0000 (14)0.0003 (15)
C20.0317 (14)0.0503 (19)0.0372 (16)0.0019 (12)0.0007 (13)0.0011 (16)
C30.0480 (17)0.0584 (18)0.0421 (18)0.0023 (14)0.0030 (17)0.0105 (17)
C40.0514 (19)0.082 (3)0.036 (2)0.0045 (18)0.0049 (15)0.0087 (19)
C50.060 (2)0.078 (3)0.0323 (18)0.0060 (18)0.0013 (15)0.0082 (18)
C60.0502 (17)0.0572 (17)0.0421 (18)0.0014 (14)0.0007 (17)0.0091 (17)
C70.0323 (14)0.0464 (18)0.0343 (15)0.0012 (11)0.0020 (13)0.0025 (14)
C80.0364 (16)0.0439 (18)0.0371 (18)0.0026 (13)0.0019 (14)0.0064 (15)
C90.0313 (15)0.0437 (17)0.0329 (15)0.0032 (13)0.0010 (11)0.0030 (15)
C100.0381 (16)0.0496 (18)0.0437 (19)0.0069 (13)0.0029 (14)0.0009 (16)
C110.0417 (16)0.0569 (19)0.0426 (17)0.0034 (13)0.0025 (17)0.0080 (18)
C120.0365 (16)0.057 (2)0.0344 (16)0.0051 (15)0.0005 (13)0.0017 (15)
C130.0478 (17)0.0547 (18)0.0391 (17)0.0037 (14)0.0021 (15)0.0065 (16)
C140.0436 (18)0.0486 (18)0.0419 (18)0.0072 (14)0.0017 (14)0.0029 (16)
C150.059 (2)0.099 (3)0.041 (2)0.001 (2)0.0073 (17)0.001 (2)
O30.102 (2)0.157 (3)0.0417 (17)0.034 (2)0.0179 (16)0.0032 (19)
Geometric parameters (Å, º) top
O1—C11.206 (3)C6—H60.9300
O2—C81.203 (3)C7—C81.487 (4)
N1—C81.394 (4)C9—C141.379 (4)
N1—C11.401 (4)C9—C101.385 (4)
N1—C91.428 (3)C10—C111.383 (4)
C1—C21.487 (5)C10—H100.9300
C2—C71.372 (4)C11—C121.379 (4)
C2—C31.382 (5)C11—H110.9300
C3—C41.392 (5)C12—C131.381 (4)
C3—H30.9300C12—C151.479 (4)
C4—C51.371 (5)C13—C141.378 (5)
C4—H40.9300C13—H130.9300
C5—C61.396 (5)C14—H140.9300
C5—H50.9300C15—O31.195 (4)
C6—C71.369 (4)C15—H150.9300
C8—N1—C1112.1 (2)O2—C8—N1125.7 (3)
C8—N1—C9122.7 (3)O2—C8—C7128.7 (3)
C1—N1—C9125.2 (3)N1—C8—C7105.6 (2)
O1—C1—N1125.3 (3)C14—C9—C10120.9 (3)
O1—C1—C2129.5 (3)C14—C9—N1119.4 (3)
N1—C1—C2105.2 (2)C10—C9—N1119.6 (3)
C7—C2—C3121.2 (3)C11—C10—C9118.7 (3)
C7—C2—C1108.7 (3)C11—C10—H10120.6
C3—C2—C1130.1 (3)C9—C10—H10120.6
C2—C3—C4117.4 (3)C12—C11—C10120.9 (3)
C2—C3—H3121.3C12—C11—H11119.5
C4—C3—H3121.3C10—C11—H11119.5
C5—C4—C3121.1 (3)C11—C12—C13119.5 (3)
C5—C4—H4119.4C11—C12—C15119.1 (3)
C3—C4—H4119.4C13—C12—C15121.4 (3)
C4—C5—C6121.0 (3)C14—C13—C12120.4 (3)
C4—C5—H5119.5C14—C13—H13119.8
C6—C5—H5119.5C12—C13—H13119.8
C7—C6—C5117.4 (3)C13—C14—C9119.5 (3)
C7—C6—H6121.3C13—C14—H14120.2
C5—C6—H6121.3C9—C14—H14120.2
C6—C7—C2121.9 (3)O3—C15—C12123.8 (4)
C6—C7—C8129.7 (3)O3—C15—H15118.1
C2—C7—C8108.4 (3)C12—C15—H15118.1
C8—N1—C1—O1179.9 (3)C9—N1—C8—C7178.0 (2)
C9—N1—C1—O11.4 (5)C6—C7—C8—O21.0 (5)
C8—N1—C1—C20.3 (3)C2—C7—C8—O2179.9 (3)
C9—N1—C1—C2179.0 (2)C6—C7—C8—N1177.6 (3)
O1—C1—C2—C7179.1 (3)C2—C7—C8—N11.5 (3)
N1—C1—C2—C71.3 (3)C8—N1—C9—C14122.7 (3)
O1—C1—C2—C30.9 (5)C1—N1—C9—C1455.9 (4)
N1—C1—C2—C3179.6 (3)C8—N1—C9—C1055.0 (4)
C7—C2—C3—C41.1 (4)C1—N1—C9—C10126.4 (3)
C1—C2—C3—C4176.9 (3)C14—C9—C10—C110.1 (4)
C2—C3—C4—C50.8 (5)N1—C9—C10—C11177.6 (3)
C3—C4—C5—C60.4 (5)C9—C10—C11—C120.6 (5)
C4—C5—C6—C70.2 (5)C10—C11—C12—C131.1 (5)
C5—C6—C7—C20.5 (4)C10—C11—C12—C15177.2 (3)
C5—C6—C7—C8179.5 (3)C11—C12—C13—C141.0 (5)
C3—C2—C7—C61.0 (4)C15—C12—C13—C14177.3 (3)
C1—C2—C7—C6177.4 (3)C12—C13—C14—C90.3 (5)
C3—C2—C7—C8179.8 (3)C10—C9—C14—C130.2 (5)
C1—C2—C7—C81.8 (3)N1—C9—C14—C13177.5 (3)
C1—N1—C8—O2179.3 (3)C11—C12—C15—O3169.4 (4)
C9—N1—C8—O20.6 (5)C13—C12—C15—O38.9 (6)
C1—N1—C8—C70.7 (3)
 

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