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The title compound, C20H15N3O3, consists a phthalo­nitrile group and an iso­indole-1,3-dione group connected by a flexible butoxy chain. The dihedral angle between these two groups is 70.47 (3)°. Partial face-to-face overlap between the phthalo­nitrile groups of centrosymmetrically related mol­ecules is observed. In addition, the crystal packing is stabilized by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009797/ci6547sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009797/ci6547Isup2.hkl
Contains datablock I

CCDC reference: 265468

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.108
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found




Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 6.70 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C8 .. 5.83 su PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C7 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C8 ... 1.44 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 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

4-[4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)butoxy]phthalonitrile top
Crystal data top
C20H15N3O3F(000) = 720
Mr = 345.35Dx = 1.351 Mg m3
Monoclinic, P21/nMelting point: 404 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 5.8020 (3) ÅCell parameters from 3884 reflections
b = 13.6911 (8) Åθ = 3.1–27.5°
c = 21.4006 (14) ŵ = 0.09 mm1
β = 92.721 (4)°T = 298 K
V = 1698.06 (17) Å3Prism, colourless
Z = 40.75 × 0.52 × 0.35 mm
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
3327 reflections with I > 2σ(I)
Radiation source: Rotating anodeRint = 0.021
Graphite Monochromator monochromatorθmax = 27.5°, θmin = 3.1°
Detector resolution: 14.6306 pixels mm-1h = 77
ω scansk = 1717
12870 measured reflectionsl = 2725
3876 independent reflections
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.2969P]
where P = (Fo2 + 2Fc2)/3
3876 reflections(Δ/σ)max = 0.001
295 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.14 e Å3
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
N10.4644 (2)0.28211 (10)0.14952 (6)0.0621 (3)
N20.4336 (2)0.19867 (11)0.02931 (7)0.0696 (4)
N30.32284 (18)0.80168 (7)0.20879 (5)0.0428 (2)
O10.36659 (15)0.50539 (6)0.09454 (4)0.0451 (2)
O20.00028 (18)0.73538 (7)0.15795 (5)0.0589 (3)
O30.60986 (18)0.90960 (7)0.24185 (5)0.0588 (3)
H10.068 (2)0.3252 (11)0.0572 (7)0.053 (4)*
H20.350 (2)0.4345 (10)0.0114 (7)0.050 (4)*
H30.003 (2)0.4292 (10)0.1516 (7)0.044 (3)*
H40.208 (3)0.5680 (10)0.1654 (7)0.051 (4)*
H50.388 (3)0.4829 (11)0.1865 (7)0.052 (4)*
H60.526 (2)0.6654 (11)0.1362 (7)0.051 (4)*
H70.703 (3)0.5812 (11)0.1567 (7)0.056 (4)*
H80.586 (3)0.6017 (12)0.2646 (8)0.061 (4)*
H90.718 (3)0.6957 (11)0.2366 (7)0.056 (4)*
H100.229 (3)0.6830 (11)0.2521 (7)0.051 (4)*
H110.409 (2)0.7471 (10)0.2927 (7)0.050 (4)*
H120.174 (3)0.9061 (12)0.0828 (8)0.066 (5)*
H130.106 (3)1.0700 (14)0.0491 (9)0.080 (5)*
H140.223 (3)1.1575 (14)0.0851 (8)0.080 (5)*
H150.493 (3)1.0834 (12)0.1587 (8)0.068 (5)*
C10.1401 (2)0.34606 (8)0.08211 (5)0.0369 (3)
C20.1257 (2)0.31444 (9)0.02003 (6)0.0405 (3)
C30.0570 (2)0.34698 (10)0.01430 (6)0.0451 (3)
C40.2181 (2)0.41018 (9)0.01196 (6)0.0433 (3)
C50.2009 (2)0.44264 (8)0.07337 (5)0.0372 (3)
C60.0219 (2)0.40998 (8)0.10879 (5)0.0371 (3)
C70.3224 (2)0.31063 (9)0.11942 (6)0.0432 (3)
C80.2975 (2)0.24958 (10)0.00739 (6)0.0486 (3)
C90.3629 (2)0.53936 (10)0.15849 (6)0.0440 (3)
C100.5539 (2)0.61322 (10)0.16703 (6)0.0446 (3)
C110.5759 (2)0.65619 (10)0.23278 (6)0.0463 (3)
C120.3764 (2)0.72001 (9)0.25126 (6)0.0451 (3)
C130.1288 (2)0.80377 (9)0.16783 (6)0.0444 (3)
C140.4405 (2)0.89066 (9)0.20873 (6)0.0429 (3)
C150.1199 (2)0.90256 (9)0.13971 (6)0.0457 (3)
C160.3114 (2)0.95366 (9)0.16283 (6)0.0436 (3)
C170.3543 (3)1.04788 (10)0.14326 (7)0.0557 (4)
C180.1958 (3)1.08918 (12)0.10044 (8)0.0671 (4)
C190.0026 (3)1.03838 (13)0.07866 (8)0.0694 (5)
C200.0395 (3)0.94318 (12)0.09769 (7)0.0594 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0556 (7)0.0641 (8)0.0669 (8)0.0152 (6)0.0074 (6)0.0101 (6)
N20.0634 (8)0.0701 (9)0.0744 (9)0.0130 (7)0.0065 (7)0.0202 (7)
N30.0482 (6)0.0395 (5)0.0405 (5)0.0084 (4)0.0016 (4)0.0043 (4)
O10.0476 (5)0.0457 (5)0.0425 (5)0.0135 (4)0.0072 (4)0.0073 (4)
O20.0586 (6)0.0566 (6)0.0612 (6)0.0228 (5)0.0011 (5)0.0082 (5)
O30.0620 (6)0.0574 (6)0.0555 (6)0.0181 (5)0.0117 (5)0.0043 (4)
C10.0377 (6)0.0326 (5)0.0401 (6)0.0004 (4)0.0014 (5)0.0038 (4)
C20.0421 (6)0.0360 (6)0.0424 (6)0.0012 (5)0.0064 (5)0.0022 (5)
C30.0507 (7)0.0468 (7)0.0376 (6)0.0008 (5)0.0013 (5)0.0063 (5)
C40.0448 (7)0.0440 (6)0.0416 (6)0.0020 (5)0.0069 (5)0.0017 (5)
C50.0393 (6)0.0326 (5)0.0394 (6)0.0011 (5)0.0002 (5)0.0001 (4)
C60.0412 (6)0.0350 (6)0.0350 (6)0.0009 (5)0.0011 (5)0.0002 (4)
C70.0431 (7)0.0396 (6)0.0465 (7)0.0053 (5)0.0042 (5)0.0031 (5)
C80.0482 (7)0.0477 (7)0.0492 (7)0.0008 (6)0.0048 (6)0.0067 (6)
C90.0479 (7)0.0427 (7)0.0417 (7)0.0095 (5)0.0065 (5)0.0085 (5)
C100.0426 (7)0.0433 (7)0.0485 (7)0.0079 (5)0.0072 (5)0.0084 (5)
C110.0465 (7)0.0462 (7)0.0460 (7)0.0087 (6)0.0007 (5)0.0044 (6)
C120.0557 (8)0.0428 (7)0.0373 (6)0.0078 (6)0.0061 (5)0.0021 (5)
C130.0460 (7)0.0464 (7)0.0411 (6)0.0096 (5)0.0058 (5)0.0088 (5)
C140.0489 (7)0.0409 (6)0.0391 (6)0.0084 (5)0.0046 (5)0.0079 (5)
C150.0500 (7)0.0457 (7)0.0416 (6)0.0024 (6)0.0037 (5)0.0076 (5)
C160.0505 (7)0.0393 (6)0.0413 (6)0.0038 (5)0.0051 (5)0.0071 (5)
C170.0670 (10)0.0422 (7)0.0579 (8)0.0053 (7)0.0043 (7)0.0027 (6)
C180.0901 (12)0.0470 (8)0.0643 (9)0.0026 (8)0.0034 (9)0.0033 (7)
C190.0821 (12)0.0639 (10)0.0613 (9)0.0157 (9)0.0070 (8)0.0035 (8)
C200.0576 (9)0.0645 (9)0.0555 (8)0.0017 (7)0.0053 (7)0.0063 (7)
Geometric parameters (Å, º) top
N1—C71.1386 (17)C10—H60.981 (15)
N2—C81.1375 (17)C10—H71.006 (16)
N3—C131.3939 (17)C11—C121.5178 (19)
N3—C141.3966 (15)C11—H81.010 (16)
N3—C121.4648 (16)C11—H90.986 (16)
O1—C51.3515 (14)C12—H100.994 (15)
O1—C91.4465 (15)C12—H110.971 (15)
O2—C131.2093 (15)C13—C151.4803 (18)
O3—C141.2119 (15)C14—C161.4834 (18)
C1—C61.3873 (16)C15—C201.376 (2)
C1—C21.4035 (16)C15—C161.3847 (18)
C1—C71.4389 (17)C16—C171.3824 (19)
C2—C31.3916 (18)C17—C181.388 (2)
C2—C81.4391 (17)C17—H150.986 (17)
C3—C41.3743 (18)C18—C191.381 (3)
C4—C51.3954 (17)C18—H141.006 (19)
C5—C61.3886 (16)C19—C201.391 (2)
C9—C101.5050 (17)C19—H130.972 (19)
C10—C111.5249 (17)C20—H120.973 (17)
C13—N3—C14111.22 (11)C12—C11—C10115.53 (11)
C13—N3—C12123.15 (10)C12—C11—H8105.7 (9)
C14—N3—C12125.25 (11)C10—C11—H8109.7 (9)
C5—O1—C9118.64 (9)C12—C11—H9107.8 (9)
C6—C1—C2120.96 (11)C10—C11—H9108.8 (9)
C6—C1—C7119.05 (10)H8—C11—H9109.2 (12)
C2—C1—C7119.97 (11)N3—C12—C11114.82 (10)
C3—C2—C1118.83 (11)N3—C12—H10104.1 (8)
C3—C2—C8120.83 (11)C11—C12—H10112.2 (8)
C1—C2—C8120.34 (11)N3—C12—H11107.5 (8)
C4—C3—C2120.42 (11)C11—C12—H11109.9 (9)
C4—C3—H1120.6 (9)H10—C12—H11107.9 (12)
C2—C3—H1119.0 (9)O2—C13—N3124.54 (13)
C3—C4—C5120.51 (12)O2—C13—C15128.82 (13)
C3—C4—H2122.2 (8)N3—C13—C15106.63 (10)
C5—C4—H2117.3 (8)O3—C14—N3124.68 (12)
O1—C5—C6124.08 (10)O3—C14—C16129.26 (12)
O1—C5—C4115.88 (10)N3—C14—C16106.03 (10)
C6—C5—C4120.04 (11)C20—C15—C16122.16 (13)
C1—C6—C5119.22 (11)C20—C15—C13130.12 (13)
C1—C6—H3117.3 (8)C16—C15—C13107.72 (11)
C5—C6—H3123.4 (8)C17—C16—C15121.08 (13)
N1—C7—C1179.06 (15)C17—C16—C14130.59 (12)
N2—C8—C2179.64 (17)C15—C16—C14108.33 (11)
O1—C9—C10106.68 (10)C16—C17—C18117.21 (15)
O1—C9—H4108.6 (8)C16—C17—H15121.1 (10)
C10—C9—H4112.4 (8)C18—C17—H15121.7 (10)
O1—C9—H5108.4 (9)C19—C18—C17121.29 (15)
C10—C9—H5111.6 (9)C19—C18—H14119.6 (10)
H4—C9—H5109.0 (12)C17—C18—H14119.1 (10)
C9—C10—C11113.59 (11)C18—C19—C20121.61 (16)
C9—C10—H6108.1 (8)C18—C19—H13119.0 (11)
C11—C10—H6110.1 (9)C20—C19—H13119.3 (11)
C9—C10—H7108.5 (8)C15—C20—C19116.63 (15)
C11—C10—H7109.6 (9)C15—C20—H12120.5 (10)
H6—C10—H7106.6 (12)C19—C20—H12122.9 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H1···O2i0.970 (15)2.326 (15)3.2765 (17)166 (1)
C6—H3···O3ii0.964 (15)2.417 (15)3.3217 (15)156 (1)
C9—H4···O20.998 (17)2.591 (15)3.4098 (16)139 (1)
C11—H9···O2iii0.986 (17)2.464 (16)3.1901 (16)130 (1)
C12—H10···O20.995 (17)2.466 (16)2.8949 (16)106 (1)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+1, y, z.
 

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