Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053226/hk2339sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053226/hk2339Isup2.hkl |
CCDC reference: 672791
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.080
- wR factor = 0.249
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.105 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.71 mm PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 1000 Deg. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. O2 .. 2.70 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 4 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
The title compound, (I), was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006a), using phthalaldehydic acid and 4-iodoaniline as starting materials (yield; 83%, m.p. 409–411 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a DMF solution at room temperature.
H19 (for NH) was located in difference syntheses and refined isotropically [N—H = 0.99 (4) Å, Uiso(H) = 0.066 (11) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.98, 0.97 and 0.96 Å, for aromatic, methine, methylene and methyl H atoms and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
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).
C18H19NO2 | Z = 2 |
Mr = 281.34 | F(000) = 300 |
Triclinic, P1 | Dx = 1.210 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8603 (7) Å | Cell parameters from 16234 reflections |
b = 7.2525 (9) Å | θ = 2.2–27.3° |
c = 18.875 (2) Å | µ = 0.08 mm−1 |
α = 89.268 (10)° | T = 296 K |
β = 82.734 (10)° | Plane, colorless |
γ = 76.045 (10)° | 0.71 × 0.33 × 0.07 mm |
V = 772.18 (16) Å3 |
Stoe IPDS-2 diffractometer | 3002 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1669 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.105 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.2° |
ω scans | h = −7→7 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.960, Tmax = 0.992 | l = −23→23 |
16234 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)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.249 | w = 1/[σ2(Fo2) + (0.0977P)2 + 0.5206P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3002 reflections | Δρmax = 0.30 e Å−3 |
195 parameters | Δρmin = −0.22 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: 0.051 (11) |
C18H19NO2 | γ = 76.045 (10)° |
Mr = 281.34 | V = 772.18 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.8603 (7) Å | Mo Kα radiation |
b = 7.2525 (9) Å | µ = 0.08 mm−1 |
c = 18.875 (2) Å | T = 296 K |
α = 89.268 (10)° | 0.71 × 0.33 × 0.07 mm |
β = 82.734 (10)° |
Stoe IPDS-2 diffractometer | 3002 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 1669 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.992 | Rint = 0.105 |
16234 measured reflections |
R[F2 > 2σ(F2)] = 0.080 | 0 restraints |
wR(F2) = 0.249 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.30 e Å−3 |
3002 reflections | Δρmin = −0.22 e Å−3 |
195 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 | 0.9390 (5) | 0.2237 (4) | 0.41838 (16) | 0.0799 (9) | |
O2 | 0.7034 (5) | 0.2755 (4) | 0.33295 (15) | 0.0698 (8) | |
N1 | 0.3062 (6) | 0.3156 (4) | 0.30706 (19) | 0.0642 (9) | |
H19 | 0.193 (7) | 0.303 (5) | 0.349 (2) | 0.066 (11)* | |
C1 | 0.7958 (7) | 0.1738 (5) | 0.3882 (2) | 0.0630 (10) | |
C2 | 0.6939 (7) | 0.0084 (5) | 0.3981 (2) | 0.0603 (10) | |
C3 | 0.7386 (7) | −0.1397 (6) | 0.4462 (2) | 0.0673 (11) | |
H3 | 0.8495 | −0.1452 | 0.4778 | 0.081* | |
C4 | 0.6142 (8) | −0.2759 (6) | 0.4454 (2) | 0.0734 (12) | |
H4 | 0.6401 | −0.3757 | 0.4772 | 0.088* | |
C5 | 0.4506 (9) | −0.2681 (6) | 0.3983 (3) | 0.0791 (13) | |
H5 | 0.3711 | −0.3646 | 0.3983 | 0.095* | |
C6 | 0.4009 (8) | −0.1202 (5) | 0.3506 (2) | 0.0702 (11) | |
H6 | 0.2865 | −0.1136 | 0.3201 | 0.084* | |
C7 | 0.5296 (7) | 0.0162 (5) | 0.3507 (2) | 0.0594 (10) | |
C8 | 0.5281 (7) | 0.1874 (5) | 0.3051 (2) | 0.0621 (10) | |
H8 | 0.5860 | 0.1452 | 0.2556 | 0.074* | |
C9 | 0.2634 (7) | 0.4695 (5) | 0.2608 (2) | 0.0601 (10) | |
C10 | 0.0367 (7) | 0.5832 (5) | 0.2629 (2) | 0.0643 (10) | |
H10 | −0.0839 | 0.5599 | 0.2962 | 0.077* | |
C11 | −0.0127 (8) | 0.7312 (5) | 0.2161 (2) | 0.0717 (11) | |
H11 | −0.1673 | 0.8049 | 0.2184 | 0.086* | |
C12 | 0.1583 (8) | 0.7737 (6) | 0.1661 (2) | 0.0704 (11) | |
C13 | 0.3872 (8) | 0.6597 (6) | 0.1651 (2) | 0.0781 (12) | |
H13 | 0.5071 | 0.6830 | 0.1316 | 0.094* | |
C14 | 0.4421 (7) | 0.5127 (6) | 0.2125 (2) | 0.0717 (11) | |
H14 | 0.5980 | 0.4432 | 0.2120 | 0.086* | |
C15 | 0.1054 (10) | 0.9338 (6) | 0.1145 (3) | 0.0890 (15) | |
H15A | 0.2080 | 0.8983 | 0.0698 | 0.107* | |
H15B | −0.0571 | 0.9523 | 0.1047 | 0.107* | |
C16 | 0.1391 (12) | 1.1171 (7) | 0.1414 (3) | 0.1084 (18) | |
H16A | 0.3021 | 1.0979 | 0.1508 | 0.130* | |
H16B | 0.0382 | 1.1507 | 0.1865 | 0.130* | |
C17 | 0.0844 (13) | 1.2847 (8) | 0.0908 (3) | 0.116 (2) | |
H17A | −0.0642 | 1.2868 | 0.0728 | 0.139* | |
H17B | 0.0636 | 1.4020 | 0.1176 | 0.139* | |
C18 | 0.2664 (14) | 1.2782 (10) | 0.0306 (4) | 0.143 (3) | |
H18A | 0.2871 | 1.1634 | 0.0033 | 0.171* | |
H18B | 0.4130 | 1.2812 | 0.0477 | 0.171* | |
H18C | 0.2198 | 1.3859 | 0.0010 | 0.171* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0755 (19) | 0.091 (2) | 0.085 (2) | −0.0365 (17) | −0.0207 (16) | 0.0157 (16) |
O2 | 0.0691 (17) | 0.0628 (16) | 0.0837 (19) | −0.0239 (13) | −0.0195 (14) | 0.0228 (14) |
N1 | 0.061 (2) | 0.0579 (19) | 0.071 (2) | −0.0118 (16) | −0.0050 (16) | 0.0156 (16) |
C1 | 0.062 (2) | 0.058 (2) | 0.068 (2) | −0.0150 (19) | −0.005 (2) | 0.0097 (19) |
C2 | 0.062 (2) | 0.054 (2) | 0.062 (2) | −0.0117 (17) | −0.0036 (18) | 0.0065 (17) |
C3 | 0.074 (3) | 0.059 (2) | 0.066 (2) | −0.010 (2) | −0.011 (2) | 0.0105 (19) |
C4 | 0.093 (3) | 0.051 (2) | 0.073 (3) | −0.015 (2) | −0.004 (2) | 0.013 (2) |
C5 | 0.100 (3) | 0.051 (2) | 0.087 (3) | −0.025 (2) | −0.004 (3) | 0.003 (2) |
C6 | 0.079 (3) | 0.050 (2) | 0.082 (3) | −0.016 (2) | −0.010 (2) | −0.006 (2) |
C7 | 0.063 (2) | 0.047 (2) | 0.064 (2) | −0.0093 (17) | −0.0004 (18) | 0.0009 (17) |
C8 | 0.067 (2) | 0.055 (2) | 0.065 (2) | −0.0164 (19) | −0.0071 (19) | 0.0053 (18) |
C9 | 0.069 (2) | 0.052 (2) | 0.063 (2) | −0.0192 (18) | −0.0152 (19) | 0.0112 (18) |
C10 | 0.063 (2) | 0.057 (2) | 0.071 (3) | −0.0130 (19) | −0.0016 (19) | 0.0022 (19) |
C11 | 0.073 (3) | 0.051 (2) | 0.086 (3) | −0.0042 (19) | −0.014 (2) | 0.005 (2) |
C12 | 0.082 (3) | 0.059 (2) | 0.072 (3) | −0.019 (2) | −0.017 (2) | 0.014 (2) |
C13 | 0.082 (3) | 0.080 (3) | 0.074 (3) | −0.024 (2) | −0.005 (2) | 0.023 (2) |
C14 | 0.065 (2) | 0.072 (3) | 0.076 (3) | −0.016 (2) | −0.004 (2) | 0.017 (2) |
C15 | 0.115 (4) | 0.068 (3) | 0.089 (3) | −0.024 (3) | −0.030 (3) | 0.019 (2) |
C16 | 0.156 (5) | 0.081 (3) | 0.098 (4) | −0.038 (3) | −0.033 (4) | 0.023 (3) |
C17 | 0.148 (5) | 0.079 (3) | 0.116 (5) | −0.025 (4) | −0.013 (4) | 0.024 (3) |
C18 | 0.178 (7) | 0.123 (5) | 0.107 (5) | −0.017 (5) | 0.015 (5) | 0.022 (4) |
N1—H19 | 0.99 (4) | C10—C11 | 1.381 (5) |
C1—O1 | 1.197 (5) | C10—H10 | 0.9300 |
C1—O2 | 1.362 (5) | C11—C12 | 1.375 (6) |
C1—C2 | 1.464 (5) | C11—H11 | 0.9300 |
C2—C7 | 1.386 (5) | C12—C13 | 1.394 (6) |
C2—C3 | 1.395 (5) | C12—C15 | 1.506 (6) |
C3—C4 | 1.363 (6) | C13—C14 | 1.387 (6) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.380 (6) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—C16 | 1.495 (7) |
C5—C6 | 1.391 (6) | C15—H15A | 0.9700 |
C5—H5 | 0.9300 | C15—H15B | 0.9700 |
C6—C7 | 1.382 (5) | C16—C17 | 1.534 (7) |
C6—H6 | 0.9300 | C16—H16A | 0.9700 |
C7—C8 | 1.501 (5) | C16—H16B | 0.9700 |
C8—N1 | 1.400 (5) | C17—C18 | 1.449 (9) |
C8—O2 | 1.484 (4) | C17—H17A | 0.9700 |
C8—H8 | 0.9800 | C17—H17B | 0.9700 |
C9—C10 | 1.381 (5) | C18—H18A | 0.9600 |
C9—C14 | 1.391 (5) | C18—H18B | 0.9600 |
C9—N1 | 1.402 (5) | C18—H18C | 0.9600 |
C1—O2—C8 | 110.5 (3) | C12—C11—C10 | 122.4 (4) |
C8—N1—C9 | 122.6 (3) | C12—C11—H11 | 118.8 |
C8—N1—H19 | 114 (2) | C10—C11—H11 | 118.8 |
C9—N1—H19 | 122 (2) | C11—C12—C13 | 116.5 (4) |
O1—C1—O2 | 120.5 (4) | C11—C12—C15 | 122.7 (4) |
O1—C1—C2 | 131.3 (4) | C13—C12—C15 | 120.8 (4) |
O2—C1—C2 | 108.2 (3) | C14—C13—C12 | 122.1 (4) |
C7—C2—C3 | 121.2 (4) | C14—C13—H13 | 118.9 |
C7—C2—C1 | 109.2 (3) | C12—C13—H13 | 118.9 |
C3—C2—C1 | 129.6 (4) | C13—C14—C9 | 119.9 (4) |
C4—C3—C2 | 117.8 (4) | C13—C14—H14 | 120.1 |
C4—C3—H3 | 121.1 | C9—C14—H14 | 120.1 |
C2—C3—H3 | 121.1 | C16—C15—C12 | 113.3 (4) |
C3—C4—C5 | 121.0 (4) | C16—C15—H15A | 108.9 |
C3—C4—H4 | 119.5 | C12—C15—H15A | 108.9 |
C5—C4—H4 | 119.5 | C16—C15—H15B | 108.9 |
C4—C5—C6 | 122.1 (4) | C12—C15—H15B | 108.9 |
C4—C5—H5 | 119.0 | H15A—C15—H15B | 107.7 |
C6—C5—H5 | 119.0 | C15—C16—C17 | 115.0 (5) |
C7—C6—C5 | 116.8 (4) | C15—C16—H16A | 108.5 |
C7—C6—H6 | 121.6 | C17—C16—H16A | 108.5 |
C5—C6—H6 | 121.6 | C15—C16—H16B | 108.5 |
C6—C7—C2 | 121.1 (3) | C17—C16—H16B | 108.5 |
C6—C7—C8 | 130.7 (4) | H16A—C16—H16B | 107.5 |
C2—C7—C8 | 108.3 (3) | C18—C17—C16 | 114.0 (6) |
N1—C8—O2 | 111.7 (3) | C18—C17—H17A | 108.8 |
N1—C8—C7 | 114.6 (3) | C16—C17—H17A | 108.8 |
O2—C8—C7 | 103.7 (3) | C18—C17—H17B | 108.8 |
N1—C8—H8 | 108.9 | C16—C17—H17B | 108.8 |
O2—C8—H8 | 108.9 | H17A—C17—H17B | 107.7 |
C7—C8—H8 | 108.9 | C17—C18—H18A | 109.5 |
C10—C9—C14 | 118.3 (3) | C17—C18—H18B | 109.5 |
C10—C9—N1 | 119.3 (3) | H18A—C18—H18B | 109.5 |
C14—C9—N1 | 122.3 (4) | C17—C18—H18C | 109.5 |
C11—C10—C9 | 120.6 (4) | H18A—C18—H18C | 109.5 |
C11—C10—H10 | 119.7 | H18B—C18—H18C | 109.5 |
C9—C10—H10 | 119.7 | ||
O1—C1—O2—C8 | −179.2 (4) | N1—C8—O2—C1 | 123.2 (3) |
C2—C1—O2—C8 | 2.3 (4) | C7—C8—O2—C1 | −0.7 (4) |
O1—C1—C2—C7 | 178.6 (4) | O2—C8—N1—C9 | 71.4 (4) |
O2—C1—C2—C7 | −3.1 (4) | C7—C8—N1—C9 | −171.0 (3) |
O1—C1—C2—C3 | −0.4 (8) | C10—C9—N1—C8 | 176.1 (4) |
O2—C1—C2—C3 | 177.9 (4) | C14—C9—N1—C8 | −4.0 (6) |
C7—C2—C3—C4 | −0.4 (6) | C14—C9—C10—C11 | 2.7 (6) |
C1—C2—C3—C4 | 178.6 (4) | N1—C9—C10—C11 | −177.4 (4) |
C2—C3—C4—C5 | 0.4 (6) | C10—C9—C14—C13 | −3.9 (6) |
C3—C4—C5—C6 | −1.4 (7) | N1—C9—C14—C13 | 176.2 (4) |
C4—C5—C6—C7 | 2.3 (6) | C9—C10—C11—C12 | −0.5 (6) |
C5—C6—C7—C2 | −2.2 (6) | C10—C11—C12—C13 | −0.4 (7) |
C5—C6—C7—C8 | 177.3 (4) | C10—C11—C12—C15 | 179.5 (4) |
C3—C2—C7—C6 | 1.4 (6) | C11—C12—C13—C14 | −0.9 (7) |
C1—C2—C7—C6 | −177.8 (4) | C15—C12—C13—C14 | 179.2 (4) |
C3—C2—C7—C8 | −178.3 (4) | C12—C13—C14—C9 | 3.1 (7) |
C1—C2—C7—C8 | 2.6 (4) | C11—C12—C15—C16 | 91.9 (6) |
C6—C7—C8—N1 | 57.2 (6) | C13—C12—C15—C16 | −88.3 (6) |
C2—C7—C8—N1 | −123.2 (4) | C12—C15—C16—C17 | −179.3 (5) |
C6—C7—C8—O2 | 179.2 (4) | C15—C16—C17—C18 | −75.8 (8) |
C2—C7—C8—O2 | −1.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H19···O1i | 0.99 (4) | 2.04 (4) | 3.000 (4) | 165 (3) |
C3—H3···O1ii | 0.93 | 2.44 | 3.331 (5) | 161 (3) |
C10—H10···O2i | 0.93 | 2.70 | 3.450 (5) | 139 (1) |
C6—H6···Cg1iii | 0.93 | 2.94 (3) | 3.635 (4) | 133 (1) |
C17—H17B···Cg1iv | 0.97 | 2.78 (3) | 3.663 (6) | 151 (1) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1; (iii) x, y−1, z; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H19NO2 |
Mr | 281.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 5.8603 (7), 7.2525 (9), 18.875 (2) |
α, β, γ (°) | 89.268 (10), 82.734 (10), 76.045 (10) |
V (Å3) | 772.18 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.71 × 0.33 × 0.07 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.960, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16234, 3002, 1669 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.080, 0.249, 1.05 |
No. of reflections | 3002 |
No. of parameters | 195 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.30, −0.22 |
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—H19···O1i | 0.99 (4) | 2.04 (4) | 3.000 (4) | 165 (3) |
C3—H3···O1ii | 0.93 | 2.44 | 3.331 (5) | 161 (3) |
C10—H10···O2i | 0.93 | 2.70 | 3.450 (5) | 138.9 (1) |
C6—H6···Cg1iii | 0.93 | 2.94 (3) | 3.635 (4) | 133.3 (4) |
C17—H17B···Cg1iv | 0.97 | 2.78 (3) | 3.663 (6) | 150.9 (4) |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y, −z+1; (iii) x, y−1, z; (iv) x, y+1, z. |
Phthalides (isobenzofuranones) possess several important properties, such as fungicidal (Aoki et al., 1973; Lacova, 1973), bactericidal and herbicidal (Lacova, 1973), analgesic (Elderfield, 1951), hypotensive and vasorelaxant activities (Tsi & Tan, 1997). Considering the potential interest of such phthalide-3-phosphonates in synthetic organic chemistry 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 supra- molecular aggregation in 3-substituted phthalides (Büyükgüngör & Odabaşoğlu, 2006a,b; Odabaşoğlu & Büyükgüngör, 2006a–r, 2007a–g), we report herein the structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). The phthalide group (C1—C8/O2) is planar, the largest deviation from the mean plane being -0.026 (4) Å (for C6). The dihedral angle between the planar phthalide group and phenyl ring is 57.92 (16)°.
In (I), the crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds and also C—H···π interactions (Table 1), which generate edge-fused R22(8)R22(10)R22(8)R42(20)R22(8)R22(10)R22(8) ring motifs (Fig. 2) (Etter, 1990). The hydrogen bonded motifs are linked to each other forming three-dimensional network (Fig. 3).