The title compound, C
20H
15N
3O
3, 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
CCDC reference: 265468
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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-1
H-isoindol-2-yl)butoxy]phthalonitrile
top
Crystal data top
C20H15N3O3 | F(000) = 720 |
Mr = 345.35 | Dx = 1.351 Mg m−3 |
Monoclinic, P21/n | Melting point: 404 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8020 (3) Å | Cell parameters from 3884 reflections |
b = 13.6911 (8) Å | θ = 3.1–27.5° |
c = 21.4006 (14) Å | µ = 0.09 mm−1 |
β = 92.721 (4)° | T = 298 K |
V = 1698.06 (17) Å3 | Prism, colourless |
Z = 4 | 0.75 × 0.52 × 0.35 mm |
Data collection top
Rigaku Mercury CCD area-detector diffractometer | 3327 reflections with I > 2σ(I) |
Radiation source: Rotating anode | Rint = 0.021 |
Graphite Monochromator monochromator | θmax = 27.5°, θmin = 3.1° |
Detector resolution: 14.6306 pixels mm-1 | h = −7→7 |
ω scans | k = −17→17 |
12870 measured reflections | l = −27→25 |
3876 independent reflections | |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | All 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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 | |
N1 | −0.4644 (2) | 0.28211 (10) | 0.14952 (6) | 0.0621 (3) | |
N2 | −0.4336 (2) | 0.19867 (11) | −0.02931 (7) | 0.0696 (4) | |
N3 | 0.32284 (18) | 0.80168 (7) | 0.20879 (5) | 0.0428 (2) | |
O1 | 0.36659 (15) | 0.50539 (6) | 0.09454 (4) | 0.0451 (2) | |
O2 | 0.00028 (18) | 0.73538 (7) | 0.15795 (5) | 0.0589 (3) | |
O3 | 0.60986 (18) | 0.90960 (7) | 0.24185 (5) | 0.0588 (3) | |
H1 | 0.068 (2) | 0.3252 (11) | −0.0572 (7) | 0.053 (4)* | |
H2 | 0.350 (2) | 0.4345 (10) | −0.0114 (7) | 0.050 (4)* | |
H3 | 0.003 (2) | 0.4292 (10) | 0.1516 (7) | 0.044 (3)* | |
H4 | 0.208 (3) | 0.5680 (10) | 0.1654 (7) | 0.051 (4)* | |
H5 | 0.388 (3) | 0.4829 (11) | 0.1865 (7) | 0.052 (4)* | |
H6 | 0.526 (2) | 0.6654 (11) | 0.1362 (7) | 0.051 (4)* | |
H7 | 0.703 (3) | 0.5812 (11) | 0.1567 (7) | 0.056 (4)* | |
H8 | 0.586 (3) | 0.6017 (12) | 0.2646 (8) | 0.061 (4)* | |
H9 | 0.718 (3) | 0.6957 (11) | 0.2366 (7) | 0.056 (4)* | |
H10 | 0.229 (3) | 0.6830 (11) | 0.2521 (7) | 0.051 (4)* | |
H11 | 0.409 (2) | 0.7471 (10) | 0.2927 (7) | 0.050 (4)* | |
H12 | −0.174 (3) | 0.9061 (12) | 0.0828 (8) | 0.066 (5)* | |
H13 | −0.106 (3) | 1.0700 (14) | 0.0491 (9) | 0.080 (5)* | |
H14 | 0.223 (3) | 1.1575 (14) | 0.0851 (8) | 0.080 (5)* | |
H15 | 0.493 (3) | 1.0834 (12) | 0.1587 (8) | 0.068 (5)* | |
C1 | −0.1401 (2) | 0.34606 (8) | 0.08211 (5) | 0.0369 (3) | |
C2 | −0.1257 (2) | 0.31444 (9) | 0.02003 (6) | 0.0405 (3) | |
C3 | 0.0570 (2) | 0.34698 (10) | −0.01430 (6) | 0.0451 (3) | |
C4 | 0.2181 (2) | 0.41018 (9) | 0.01196 (6) | 0.0433 (3) | |
C5 | 0.2009 (2) | 0.44264 (8) | 0.07337 (5) | 0.0372 (3) | |
C6 | 0.0219 (2) | 0.40998 (8) | 0.10879 (5) | 0.0371 (3) | |
C7 | −0.3224 (2) | 0.31063 (9) | 0.11942 (6) | 0.0432 (3) | |
C8 | −0.2975 (2) | 0.24958 (10) | −0.00739 (6) | 0.0486 (3) | |
C9 | 0.3629 (2) | 0.53936 (10) | 0.15849 (6) | 0.0440 (3) | |
C10 | 0.5539 (2) | 0.61322 (10) | 0.16703 (6) | 0.0446 (3) | |
C11 | 0.5759 (2) | 0.65619 (10) | 0.23278 (6) | 0.0463 (3) | |
C12 | 0.3764 (2) | 0.72001 (9) | 0.25126 (6) | 0.0451 (3) | |
C13 | 0.1288 (2) | 0.80377 (9) | 0.16783 (6) | 0.0444 (3) | |
C14 | 0.4405 (2) | 0.89066 (9) | 0.20873 (6) | 0.0429 (3) | |
C15 | 0.1199 (2) | 0.90256 (9) | 0.13971 (6) | 0.0457 (3) | |
C16 | 0.3114 (2) | 0.95366 (9) | 0.16283 (6) | 0.0436 (3) | |
C17 | 0.3543 (3) | 1.04788 (10) | 0.14326 (7) | 0.0557 (4) | |
C18 | 0.1958 (3) | 1.08918 (12) | 0.10044 (8) | 0.0671 (4) | |
C19 | 0.0026 (3) | 1.03838 (13) | 0.07866 (8) | 0.0694 (5) | |
C20 | −0.0395 (3) | 0.94318 (12) | 0.09769 (7) | 0.0594 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0556 (7) | 0.0641 (8) | 0.0669 (8) | −0.0152 (6) | 0.0074 (6) | 0.0101 (6) |
N2 | 0.0634 (8) | 0.0701 (9) | 0.0744 (9) | −0.0130 (7) | −0.0065 (7) | −0.0202 (7) |
N3 | 0.0482 (6) | 0.0395 (5) | 0.0405 (5) | −0.0084 (4) | 0.0016 (4) | −0.0043 (4) |
O1 | 0.0476 (5) | 0.0457 (5) | 0.0425 (5) | −0.0135 (4) | 0.0072 (4) | −0.0073 (4) |
O2 | 0.0586 (6) | 0.0566 (6) | 0.0612 (6) | −0.0228 (5) | −0.0011 (5) | −0.0082 (5) |
O3 | 0.0620 (6) | 0.0574 (6) | 0.0555 (6) | −0.0181 (5) | −0.0117 (5) | −0.0043 (4) |
C1 | 0.0377 (6) | 0.0326 (5) | 0.0401 (6) | 0.0004 (4) | −0.0014 (5) | 0.0038 (4) |
C2 | 0.0421 (6) | 0.0360 (6) | 0.0424 (6) | 0.0012 (5) | −0.0064 (5) | −0.0022 (5) |
C3 | 0.0507 (7) | 0.0468 (7) | 0.0376 (6) | 0.0008 (5) | 0.0013 (5) | −0.0063 (5) |
C4 | 0.0448 (7) | 0.0440 (6) | 0.0416 (6) | −0.0020 (5) | 0.0069 (5) | −0.0017 (5) |
C5 | 0.0393 (6) | 0.0326 (5) | 0.0394 (6) | −0.0011 (5) | 0.0002 (5) | 0.0001 (4) |
C6 | 0.0412 (6) | 0.0350 (6) | 0.0350 (6) | −0.0009 (5) | 0.0011 (5) | 0.0002 (4) |
C7 | 0.0431 (7) | 0.0396 (6) | 0.0465 (7) | −0.0053 (5) | −0.0042 (5) | 0.0031 (5) |
C8 | 0.0482 (7) | 0.0477 (7) | 0.0492 (7) | −0.0008 (6) | −0.0048 (6) | −0.0067 (6) |
C9 | 0.0479 (7) | 0.0427 (7) | 0.0417 (7) | −0.0095 (5) | 0.0065 (5) | −0.0085 (5) |
C10 | 0.0426 (7) | 0.0433 (7) | 0.0485 (7) | −0.0079 (5) | 0.0072 (5) | −0.0084 (5) |
C11 | 0.0465 (7) | 0.0462 (7) | 0.0460 (7) | −0.0087 (6) | −0.0007 (5) | −0.0044 (6) |
C12 | 0.0557 (8) | 0.0428 (7) | 0.0373 (6) | −0.0078 (6) | 0.0061 (5) | −0.0021 (5) |
C13 | 0.0460 (7) | 0.0464 (7) | 0.0411 (6) | −0.0096 (5) | 0.0058 (5) | −0.0088 (5) |
C14 | 0.0489 (7) | 0.0409 (6) | 0.0391 (6) | −0.0084 (5) | 0.0046 (5) | −0.0079 (5) |
C15 | 0.0500 (7) | 0.0457 (7) | 0.0416 (6) | −0.0024 (6) | 0.0037 (5) | −0.0076 (5) |
C16 | 0.0505 (7) | 0.0393 (6) | 0.0413 (6) | −0.0038 (5) | 0.0051 (5) | −0.0071 (5) |
C17 | 0.0670 (10) | 0.0422 (7) | 0.0579 (8) | −0.0053 (7) | 0.0043 (7) | −0.0027 (6) |
C18 | 0.0901 (12) | 0.0470 (8) | 0.0643 (9) | 0.0026 (8) | 0.0034 (9) | 0.0033 (7) |
C19 | 0.0821 (12) | 0.0639 (10) | 0.0613 (9) | 0.0157 (9) | −0.0070 (8) | 0.0035 (8) |
C20 | 0.0576 (9) | 0.0645 (9) | 0.0555 (8) | 0.0017 (7) | −0.0053 (7) | −0.0063 (7) |
Geometric parameters (Å, º) top
N1—C7 | 1.1386 (17) | C10—H6 | 0.981 (15) |
N2—C8 | 1.1375 (17) | C10—H7 | 1.006 (16) |
N3—C13 | 1.3939 (17) | C11—C12 | 1.5178 (19) |
N3—C14 | 1.3966 (15) | C11—H8 | 1.010 (16) |
N3—C12 | 1.4648 (16) | C11—H9 | 0.986 (16) |
O1—C5 | 1.3515 (14) | C12—H10 | 0.994 (15) |
O1—C9 | 1.4465 (15) | C12—H11 | 0.971 (15) |
O2—C13 | 1.2093 (15) | C13—C15 | 1.4803 (18) |
O3—C14 | 1.2119 (15) | C14—C16 | 1.4834 (18) |
C1—C6 | 1.3873 (16) | C15—C20 | 1.376 (2) |
C1—C2 | 1.4035 (16) | C15—C16 | 1.3847 (18) |
C1—C7 | 1.4389 (17) | C16—C17 | 1.3824 (19) |
C2—C3 | 1.3916 (18) | C17—C18 | 1.388 (2) |
C2—C8 | 1.4391 (17) | C17—H15 | 0.986 (17) |
C3—C4 | 1.3743 (18) | C18—C19 | 1.381 (3) |
C4—C5 | 1.3954 (17) | C18—H14 | 1.006 (19) |
C5—C6 | 1.3886 (16) | C19—C20 | 1.391 (2) |
C9—C10 | 1.5050 (17) | C19—H13 | 0.972 (19) |
C10—C11 | 1.5249 (17) | C20—H12 | 0.973 (17) |
| | | |
C13—N3—C14 | 111.22 (11) | C12—C11—C10 | 115.53 (11) |
C13—N3—C12 | 123.15 (10) | C12—C11—H8 | 105.7 (9) |
C14—N3—C12 | 125.25 (11) | C10—C11—H8 | 109.7 (9) |
C5—O1—C9 | 118.64 (9) | C12—C11—H9 | 107.8 (9) |
C6—C1—C2 | 120.96 (11) | C10—C11—H9 | 108.8 (9) |
C6—C1—C7 | 119.05 (10) | H8—C11—H9 | 109.2 (12) |
C2—C1—C7 | 119.97 (11) | N3—C12—C11 | 114.82 (10) |
C3—C2—C1 | 118.83 (11) | N3—C12—H10 | 104.1 (8) |
C3—C2—C8 | 120.83 (11) | C11—C12—H10 | 112.2 (8) |
C1—C2—C8 | 120.34 (11) | N3—C12—H11 | 107.5 (8) |
C4—C3—C2 | 120.42 (11) | C11—C12—H11 | 109.9 (9) |
C4—C3—H1 | 120.6 (9) | H10—C12—H11 | 107.9 (12) |
C2—C3—H1 | 119.0 (9) | O2—C13—N3 | 124.54 (13) |
C3—C4—C5 | 120.51 (12) | O2—C13—C15 | 128.82 (13) |
C3—C4—H2 | 122.2 (8) | N3—C13—C15 | 106.63 (10) |
C5—C4—H2 | 117.3 (8) | O3—C14—N3 | 124.68 (12) |
O1—C5—C6 | 124.08 (10) | O3—C14—C16 | 129.26 (12) |
O1—C5—C4 | 115.88 (10) | N3—C14—C16 | 106.03 (10) |
C6—C5—C4 | 120.04 (11) | C20—C15—C16 | 122.16 (13) |
C1—C6—C5 | 119.22 (11) | C20—C15—C13 | 130.12 (13) |
C1—C6—H3 | 117.3 (8) | C16—C15—C13 | 107.72 (11) |
C5—C6—H3 | 123.4 (8) | C17—C16—C15 | 121.08 (13) |
N1—C7—C1 | 179.06 (15) | C17—C16—C14 | 130.59 (12) |
N2—C8—C2 | 179.64 (17) | C15—C16—C14 | 108.33 (11) |
O1—C9—C10 | 106.68 (10) | C16—C17—C18 | 117.21 (15) |
O1—C9—H4 | 108.6 (8) | C16—C17—H15 | 121.1 (10) |
C10—C9—H4 | 112.4 (8) | C18—C17—H15 | 121.7 (10) |
O1—C9—H5 | 108.4 (9) | C19—C18—C17 | 121.29 (15) |
C10—C9—H5 | 111.6 (9) | C19—C18—H14 | 119.6 (10) |
H4—C9—H5 | 109.0 (12) | C17—C18—H14 | 119.1 (10) |
C9—C10—C11 | 113.59 (11) | C18—C19—C20 | 121.61 (16) |
C9—C10—H6 | 108.1 (8) | C18—C19—H13 | 119.0 (11) |
C11—C10—H6 | 110.1 (9) | C20—C19—H13 | 119.3 (11) |
C9—C10—H7 | 108.5 (8) | C15—C20—C19 | 116.63 (15) |
C11—C10—H7 | 109.6 (9) | C15—C20—H12 | 120.5 (10) |
H6—C10—H7 | 106.6 (12) | C19—C20—H12 | 122.9 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H1···O2i | 0.970 (15) | 2.326 (15) | 3.2765 (17) | 166 (1) |
C6—H3···O3ii | 0.964 (15) | 2.417 (15) | 3.3217 (15) | 156 (1) |
C9—H4···O2 | 0.998 (17) | 2.591 (15) | 3.4098 (16) | 139 (1) |
C11—H9···O2iii | 0.986 (17) | 2.464 (16) | 3.1901 (16) | 130 (1) |
C12—H10···O2 | 0.995 (17) | 2.466 (16) | 2.8949 (16) | 106 (1) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x+1, y, z. |