Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049677/hk2338sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049677/hk2338Isup2.hkl |
CCDC reference: 667379
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.095
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 6.23 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 6.59 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N2 .. 2.78 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. N2 .. 2.70 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Büyükgüngör & Odabaşoğlu (2006a,b, 2007); Odabaşoğlu & Büyükgüngör (2006a,b,c,d,e,f,g,h,i,j,k,l,m,n,o,p,q,r, 2007a,b,c,d). For related literature, see: Aoki et al. (1973); Lacova (1973); Elderfield (1951); Tsi & Tan (1997); Bellasio (1974); Roy & Sarkar (2005). For general background, see: Etter (1990).
The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006a), using phthalaldehydic acid and 2-hydroxy-5-chloroaniline as starting materials (yield; 80%; m.p. 420–422 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (95%) at room temperature.
H atoms were located in a difference syntheses and refined isotropically [N—H = 0.88 (2) Å, Uiso(H) = 0.101 (7) Å2 and C—H = 0.93 (3)–1.02 (2) Å, Uiso(H) = 0.075 (5)–0.149 (10) Å2].
Phthalides (isobenzofuranones) possess several important properties, such as fungicidal (Aoki et al., 1973; Lacova, 1973), bactericidal and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), hypertensive and vasorelaxant activities (Tsi & Tan, 1997). In addition, phthalide derivatives are useful in the treatment of circulatory and heart-related diseases (Bellasio, 1974). They are also found to be associated with pesticidal activities (Roy & Sarkar, 2005). Considering the potential interest of such phthalide-3-phosphonates in synthetic organic chemistry, and as agrochemical and pharmaceutical agents, we decided to investigate the solid-state structures of 3-substituted phthalides by X-ray diffraction methods. As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides, we report herein the structure of the title compound, (I).
The geometry of the title molecule, (I), (Fig. 1) does not show any significant difference from the average geometry found for 3-anilinoisobenzofuran-1(3H) -ones (Büyükgüngör & Odabaşoğlu, 2006a,b, 2007; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b,c). The phthalide group (C1—C8/O2) is planar, the largest deviation from the mean plane being -0.017 (2) Å (for C2). The dihedral angle between the planar phthalide group and phenyl ring is 83.21 (9)°.
In (I), the crystal packing is stabilized by intermolecular N—H···O and C—H···N hydrogen bonds (Table 1, Fig. 2), which generate edge-fused R21(6)R44(24)R21(6) ring motifs (Etter, 1990). These motifs also generate a three dimensional network by C—H···π and π···π interactions (Table 1, Fig. 3), where the π···π interactions occur between (C2—C7) and (C9—C14) rings and their symmetry-related counterparts [symmetry code: x, 1/2 - y, 1/2 + z], with a centroid-to-centroid distance of 3.822 (1) Å and a plane to plane separation of 3.697 Å.
For related structures, see: Büyükgüngör & Odabaşoğlu (2006a,b, 2007); Odabaşoğlu & Büyükgüngör (2006a,b,c,d,e,f,g,h,i,j,k,l,m,n,o,p,q,r, 2007a,b,c,d). For related literature, see: Aoki et al. (1973); Lacova (1973); Elderfield (1951); Tsi & Tan (1997); Bellasio (1974); Roy & Sarkar (2005). For general background, see: Etter (1990).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H12N2O2 | F(000) = 1008 |
Mr = 240.26 | Dx = 1.292 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 11933 reflections |
a = 10.1367 (7) Å | θ = 1.8–27.2° |
b = 22.519 (2) Å | µ = 0.09 mm−1 |
c = 10.8253 (8) Å | T = 296 K |
V = 2471.0 (3) Å3 | Prism, colorless |
Z = 8 | 0.64 × 0.36 × 0.14 mm |
Stoe IPDSII diffractometer | 2437 independent reflections |
Radiation source: fine-focus sealed tube | 1265 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −27→27 |
Tmin = 0.970, Tmax = 0.990 | l = −13→13 |
17021 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | All H-atom parameters refined |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.89 | (Δ/σ)max < 0.001 |
2437 reflections | Δρmax = 0.09 e Å−3 |
212 parameters | Δρmin = −0.09 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0065 (8) |
C14H12N2O2 | V = 2471.0 (3) Å3 |
Mr = 240.26 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.1367 (7) Å | µ = 0.09 mm−1 |
b = 22.519 (2) Å | T = 296 K |
c = 10.8253 (8) Å | 0.64 × 0.36 × 0.14 mm |
Stoe IPDSII diffractometer | 2437 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1265 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.990 | Rint = 0.056 |
17021 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.095 | All H-atom parameters refined |
S = 0.89 | Δρmax = 0.09 e Å−3 |
2437 reflections | Δρmin = −0.09 e Å−3 |
212 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.04032 (18) | 0.07038 (8) | 0.25289 (16) | 0.1286 (6) | |
O2 | 0.90927 (13) | 0.10288 (5) | 0.40304 (13) | 0.0841 (4) | |
N1 | 0.68545 (16) | 0.10890 (7) | 0.46993 (17) | 0.0761 (4) | |
N2 | 0.75182 (13) | 0.18310 (6) | 0.60452 (13) | 0.0676 (4) | |
C1 | 0.9574 (2) | 0.06011 (9) | 0.3292 (2) | 0.0861 (6) | |
C2 | 0.89111 (19) | 0.00431 (7) | 0.35851 (16) | 0.0757 (5) | |
C3 | 0.9070 (3) | −0.05216 (11) | 0.3075 (2) | 0.0988 (7) | |
C4 | 0.8291 (4) | −0.09672 (11) | 0.3527 (3) | 0.1144 (9) | |
C5 | 0.7376 (3) | −0.08594 (11) | 0.4421 (3) | 0.1152 (9) | |
C6 | 0.7198 (3) | −0.03037 (10) | 0.4921 (2) | 0.0935 (7) | |
C7 | 0.79959 (19) | 0.01458 (7) | 0.44879 (16) | 0.0699 (5) | |
C8 | 0.80476 (19) | 0.07843 (7) | 0.48549 (19) | 0.0697 (5) | |
C9 | 0.66928 (16) | 0.16633 (7) | 0.51600 (16) | 0.0662 (5) | |
C10 | 0.56963 (19) | 0.20219 (10) | 0.4707 (2) | 0.0774 (5) | |
C11 | 0.5581 (2) | 0.25831 (10) | 0.5175 (2) | 0.0854 (6) | |
C12 | 0.6424 (2) | 0.27651 (10) | 0.6096 (2) | 0.0822 (6) | |
C13 | 0.73612 (17) | 0.23811 (8) | 0.65240 (16) | 0.0698 (5) | |
C14 | 0.8268 (3) | 0.25249 (12) | 0.7571 (2) | 0.0890 (6) | |
H1 | 0.642 (2) | 0.0998 (9) | 0.402 (2) | 0.101 (7)* | |
H3 | 0.975 (2) | −0.0544 (9) | 0.2473 (19) | 0.097 (7)* | |
H4 | 0.846 (2) | −0.1345 (13) | 0.322 (3) | 0.149 (10)* | |
H5 | 0.681 (2) | −0.1199 (13) | 0.470 (2) | 0.145 (9)* | |
H6 | 0.652 (2) | −0.0223 (10) | 0.555 (2) | 0.127 (9)* | |
H8 | 0.8356 (16) | 0.0860 (7) | 0.5700 (17) | 0.075 (5)* | |
H10 | 0.5152 (18) | 0.1888 (8) | 0.4067 (18) | 0.092 (6)* | |
H11 | 0.489 (2) | 0.2842 (10) | 0.4852 (17) | 0.104 (7)* | |
H12 | 0.6383 (19) | 0.3151 (9) | 0.6451 (19) | 0.104 (7)* | |
H14A | 0.796 (2) | 0.2350 (10) | 0.839 (2) | 0.125 (8)* | |
H14B | 0.838 (2) | 0.2951 (12) | 0.767 (2) | 0.133 (8)* | |
H14C | 0.914 (3) | 0.2369 (10) | 0.741 (2) | 0.131 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1376 (13) | 0.1322 (14) | 0.1159 (12) | −0.0053 (11) | 0.0510 (11) | 0.0183 (10) |
O2 | 0.0910 (9) | 0.0629 (7) | 0.0984 (9) | −0.0112 (7) | 0.0080 (8) | 0.0032 (7) |
N1 | 0.0799 (11) | 0.0667 (9) | 0.0816 (11) | 0.0010 (8) | −0.0150 (9) | −0.0069 (8) |
N2 | 0.0709 (9) | 0.0630 (9) | 0.0688 (9) | −0.0049 (7) | −0.0005 (7) | −0.0018 (7) |
C1 | 0.0979 (15) | 0.0846 (14) | 0.0760 (13) | 0.0008 (12) | 0.0063 (12) | 0.0061 (11) |
C2 | 0.0993 (14) | 0.0608 (11) | 0.0671 (11) | 0.0033 (10) | −0.0075 (10) | 0.0013 (9) |
C3 | 0.132 (2) | 0.0886 (17) | 0.0760 (14) | 0.0162 (15) | −0.0067 (15) | −0.0102 (12) |
C4 | 0.173 (3) | 0.0621 (15) | 0.108 (2) | 0.0023 (17) | −0.029 (2) | −0.0098 (14) |
C5 | 0.156 (3) | 0.0672 (16) | 0.123 (2) | −0.0222 (16) | −0.0116 (19) | 0.0085 (15) |
C6 | 0.1133 (18) | 0.0702 (14) | 0.0970 (16) | −0.0151 (12) | 0.0007 (14) | 0.0097 (12) |
C7 | 0.0862 (12) | 0.0593 (10) | 0.0641 (10) | −0.0044 (9) | −0.0073 (10) | 0.0030 (9) |
C8 | 0.0821 (12) | 0.0608 (10) | 0.0662 (12) | −0.0044 (9) | −0.0026 (10) | −0.0005 (9) |
C9 | 0.0693 (11) | 0.0625 (11) | 0.0669 (11) | −0.0044 (9) | 0.0053 (9) | 0.0021 (8) |
C10 | 0.0692 (12) | 0.0848 (14) | 0.0781 (12) | 0.0037 (10) | −0.0038 (11) | 0.0058 (11) |
C11 | 0.0792 (14) | 0.0812 (14) | 0.0958 (16) | 0.0155 (11) | 0.0072 (12) | 0.0070 (12) |
C12 | 0.0846 (14) | 0.0691 (13) | 0.0930 (15) | 0.0054 (11) | 0.0195 (12) | −0.0039 (11) |
C13 | 0.0717 (11) | 0.0647 (11) | 0.0730 (11) | −0.0081 (9) | 0.0128 (9) | −0.0058 (9) |
C14 | 0.0944 (17) | 0.0871 (15) | 0.0855 (16) | −0.0145 (14) | 0.0044 (13) | −0.0210 (12) |
C1—O1 | 1.201 (2) | C8—H8 | 0.982 (18) |
C1—O2 | 1.343 (2) | C9—N2 | 1.327 (2) |
C1—C2 | 1.460 (3) | C9—C10 | 1.383 (2) |
C2—C7 | 1.367 (2) | C9—N1 | 1.396 (2) |
C2—C3 | 1.396 (3) | C10—C11 | 1.367 (3) |
C3—C4 | 1.367 (4) | C10—H10 | 0.94 (2) |
C3—H3 | 0.95 (2) | C11—C12 | 1.376 (3) |
C4—C5 | 1.363 (4) | C11—H11 | 0.97 (2) |
C4—H4 | 0.93 (3) | C12—C13 | 1.365 (3) |
C5—C6 | 1.375 (4) | C12—H12 | 0.95 (2) |
C5—H5 | 1.00 (3) | C13—N2 | 1.352 (2) |
C6—C7 | 1.378 (3) | C13—C14 | 1.495 (3) |
C6—H6 | 0.99 (2) | C14—H14A | 1.02 (2) |
C7—C8 | 1.493 (2) | C14—H14B | 0.97 (3) |
C8—N1 | 1.401 (2) | C14—H14C | 0.97 (2) |
C8—O2 | 1.491 (2) | N1—H1 | 0.88 (2) |
O1—C1—O2 | 121.7 (2) | N2—C9—C10 | 123.38 (17) |
O1—C1—C2 | 129.6 (2) | N2—C9—N1 | 116.60 (16) |
O2—C1—C2 | 108.70 (18) | C10—C9—N1 | 120.01 (18) |
C7—C2—C3 | 121.0 (2) | C11—C10—C9 | 118.1 (2) |
C7—C2—C1 | 108.79 (16) | C11—C10—H10 | 121.5 (12) |
C3—C2—C1 | 130.2 (2) | C9—C10—H10 | 120.3 (12) |
C4—C3—C2 | 117.4 (3) | C10—C11—C12 | 119.4 (2) |
C4—C3—H3 | 128.7 (13) | C10—C11—H11 | 118.7 (12) |
C2—C3—H3 | 113.8 (13) | C12—C11—H11 | 121.9 (12) |
C5—C4—C3 | 121.1 (3) | C13—C12—C11 | 119.3 (2) |
C5—C4—H4 | 122.9 (17) | C13—C12—H12 | 118.2 (12) |
C3—C4—H4 | 115.9 (17) | C11—C12—H12 | 122.5 (12) |
C4—C5—C6 | 122.1 (3) | N2—C13—C12 | 122.15 (18) |
C4—C5—H5 | 118.0 (15) | N2—C13—C14 | 114.63 (18) |
C6—C5—H5 | 120.0 (15) | C12—C13—C14 | 123.20 (19) |
C5—C6—C7 | 117.2 (3) | C13—C14—H14A | 112.6 (13) |
C5—C6—H6 | 122.1 (14) | C13—C14—H14B | 111.6 (14) |
C7—C6—H6 | 120.7 (14) | H14A—C14—H14B | 108.8 (19) |
C2—C7—C6 | 121.15 (19) | C13—C14—H14C | 110.4 (14) |
C2—C7—C8 | 109.23 (16) | H14A—C14—H14C | 107 (2) |
C6—C7—C8 | 129.63 (19) | H14B—C14—H14C | 106 (2) |
N1—C8—O2 | 111.15 (15) | C9—N1—C8 | 120.81 (16) |
N1—C8—C7 | 114.17 (16) | C9—N1—H1 | 117.0 (13) |
O2—C8—C7 | 102.79 (14) | C8—N1—H1 | 114.8 (13) |
N1—C8—H8 | 107.6 (10) | C9—N2—C13 | 117.60 (15) |
O2—C8—H8 | 105.5 (10) | C1—O2—C8 | 110.47 (14) |
C7—C8—H8 | 115.2 (9) | ||
O1—C1—C2—C7 | −177.3 (2) | N2—C9—C10—C11 | 1.8 (3) |
O2—C1—C2—C7 | 1.7 (2) | N1—C9—C10—C11 | −179.36 (17) |
O1—C1—C2—C3 | 1.0 (4) | C9—C10—C11—C12 | −1.9 (3) |
O2—C1—C2—C3 | −179.99 (19) | C10—C11—C12—C13 | 0.1 (3) |
C7—C2—C3—C4 | −1.0 (3) | C11—C12—C13—N2 | 2.1 (3) |
C1—C2—C3—C4 | −179.2 (2) | C11—C12—C13—C14 | −176.25 (19) |
C2—C3—C4—C5 | 1.5 (4) | N2—C9—N1—C8 | −20.1 (2) |
C3—C4—C5—C6 | −0.7 (4) | C10—C9—N1—C8 | 160.99 (17) |
C4—C5—C6—C7 | −0.6 (4) | O2—C8—N1—C9 | −73.3 (2) |
C3—C2—C7—C6 | −0.2 (3) | C7—C8—N1—C9 | 170.95 (16) |
C1—C2—C7—C6 | 178.32 (18) | C10—C9—N2—C13 | 0.3 (2) |
C3—C2—C7—C8 | 179.97 (18) | N1—C9—N2—C13 | −178.60 (15) |
C1—C2—C7—C8 | −1.5 (2) | C12—C13—N2—C9 | −2.3 (2) |
C5—C6—C7—C2 | 1.0 (3) | C14—C13—N2—C9 | 176.23 (16) |
C5—C6—C7—C8 | −179.2 (2) | O1—C1—O2—C8 | 177.9 (2) |
C2—C7—C8—N1 | 121.33 (18) | C2—C1—O2—C8 | −1.1 (2) |
C6—C7—C8—N1 | −58.5 (3) | N1—C8—O2—C1 | −122.34 (17) |
C2—C7—C8—O2 | 0.84 (19) | C7—C8—O2—C1 | 0.2 (2) |
C6—C7—C8—O2 | −178.99 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (2) | 2.08 (2) | 2.955 (2) | 174.9 (19) |
C4—H4···N2ii | 0.93 (3) | 2.78 (3) | 3.417 (3) | 126.99 (18) |
C11—H11···N2iii | 0.97 (2) | 2.70 (2) | 3.623 (2) | 158.83 (19) |
C14—H14A···Cg1iv | 1.02 (2) | 2.98 (2) | 3.780 (3) | 136.3 (2) |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+3/2, −y, z−1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H12N2O2 |
Mr | 240.26 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 296 |
a, b, c (Å) | 10.1367 (7), 22.519 (2), 10.8253 (8) |
V (Å3) | 2471.0 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.64 × 0.36 × 0.14 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.970, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17021, 2437, 1265 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 0.89 |
No. of reflections | 2437 |
No. of parameters | 212 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.09, −0.09 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (2) | 2.08 (2) | 2.955 (2) | 174.9 (19) |
C4—H4···N2ii | 0.93 (3) | 2.78 (3) | 3.417 (3) | 126.99 (18) |
C11—H11···N2iii | 0.97 (2) | 2.70 (2) | 3.623 (2) | 158.83 (19) |
C14—H14A···Cg1iv | 1.02 (2) | 2.98 (2) | 3.780 (3) | 136.3 (2) |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x+3/2, −y, z−1/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x, −y+1/2, z+1/2. |
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Phthalides (isobenzofuranones) possess several important properties, such as fungicidal (Aoki et al., 1973; Lacova, 1973), bactericidal and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), hypertensive and vasorelaxant activities (Tsi & Tan, 1997). In addition, phthalide derivatives are useful in the treatment of circulatory and heart-related diseases (Bellasio, 1974). They are also found to be associated with pesticidal activities (Roy & Sarkar, 2005). Considering the potential interest of such phthalide-3-phosphonates in synthetic organic chemistry, and as agrochemical and pharmaceutical agents, we decided to investigate the solid-state structures of 3-substituted phthalides by X-ray diffraction methods. As part of a continuing study of the interplay between molecular conformation and supramolecular aggregation in 3-substituted phthalides, we report herein the structure of the title compound, (I).
The geometry of the title molecule, (I), (Fig. 1) does not show any significant difference from the average geometry found for 3-anilinoisobenzofuran-1(3H) -ones (Büyükgüngör & Odabaşoğlu, 2006a,b, 2007; Odabaşoğlu & Büyükgüngör, 2006a,b, 2007a,b,c). The phthalide group (C1—C8/O2) is planar, the largest deviation from the mean plane being -0.017 (2) Å (for C2). The dihedral angle between the planar phthalide group and phenyl ring is 83.21 (9)°.
In (I), the crystal packing is stabilized by intermolecular N—H···O and C—H···N hydrogen bonds (Table 1, Fig. 2), which generate edge-fused R21(6)R44(24)R21(6) ring motifs (Etter, 1990). These motifs also generate a three dimensional network by C—H···π and π···π interactions (Table 1, Fig. 3), where the π···π interactions occur between (C2—C7) and (C9—C14) rings and their symmetry-related counterparts [symmetry code: x, 1/2 - y, 1/2 + z], with a centroid-to-centroid distance of 3.822 (1) Å and a plane to plane separation of 3.697 Å.