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The crystal structure of the title compound, C23H17NO4, is stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds and C—H...π inter­actions. The C—H...O hydrogen bonds link the mol­ecules into ladders whose uprights form C(7) chains and whose rungs enclose R22(28) rings. These motifs generate a three-dimensional network by N—H...O hydrogen bonds and C—H...π inter­actions. The phthalide ring systems of the mol­ecule are almost planar and form dihedral angles of 64.1 (3) and 88.3 (3)° with the benzene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051063/at2176sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051063/at2176Isup2.hkl
Contains datablock I

CCDC reference: 633588

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.061
  • wR factor = 0.184
  • Data-to-parameter ratio = 6.2

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 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.17 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. O1 .. 2.62 Ang. PLAT731_ALERT_1_C Bond Calc 0.87(7), Rep 0.88(2) ...... 3.50 su-Ra N1 -H1 1.555 1.555 PLAT745_ALERT_1_C D-H Calc 0.87(7), Rep 0.86000 ...... Missing su N1 -H1 1.555 1.555 PLAT746_ALERT_1_C H...A Calc 2.27(6), Rep 2.26000 ...... Missing su H1 -O1 1.555 1.565
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 25.05 From the CIF: _reflns_number_total 1592 Count of symmetry unique reflns 1597 Completeness (_total/calc) 99.69% 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 PLAT792_ALERT_1_G Check the Absolute Configuration of C8 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C16 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; 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).

[2-Methyl-4-(3-oxo-1,3-dihydroisobenzofuran-1-ylamino)phenyl]isobenzofuran- 1(3H)-one top
Crystal data top
C23H17NO4F(000) = 388
Mr = 371.38Dx = 1.370 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 7767 reflections
a = 5.1039 (3) Åθ = 1.4–25.0°
b = 6.1761 (6) ŵ = 0.09 mm1
c = 28.5758 (18) ÅT = 296 K
β = 92.444 (5)°Prism, light brown
V = 899.95 (12) Å30.54 × 0.30 × 0.12 mm
Z = 2
Data collection top
Stoe IPDS-2
diffractometer
1592 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus'1251 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.102
Detector resolution: 6.67 pixels mm-1θmax = 25.1°, θmin = 1.4°
ω scansh = 66
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 77
Tmin = 0.963, Tmax = 0.990l = 3333
8708 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.185 w = 1/[σ2(Fo2) + (0.1066P)2 + 0.2251P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1592 reflectionsΔρmax = 0.27 e Å3
258 parametersΔρmin = 0.19 e Å3
3 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (13)
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
C10.2238 (15)0.0386 (11)0.3986 (3)0.0722 (17)
C20.0468 (13)0.1036 (9)0.4237 (2)0.0616 (14)
C30.0572 (17)0.0779 (11)0.4675 (3)0.0764 (18)
H30.01660.04180.48610.092*
C40.2249 (17)0.2397 (11)0.4820 (3)0.080 (2)
H40.29990.22880.51100.096*
C50.2815 (15)0.4182 (12)0.4534 (2)0.0738 (18)
H50.39260.52530.46390.089*
C60.1776 (13)0.4399 (11)0.4102 (2)0.0673 (16)
H60.21450.56070.39160.081*
C70.0174 (12)0.2778 (10)0.3952 (2)0.0606 (14)
C80.1114 (13)0.2502 (10)0.3495 (2)0.0623 (15)
H80.02390.22720.32460.075*
C90.3990 (13)0.4331 (10)0.2953 (2)0.0620 (15)
C100.5739 (13)0.5989 (10)0.2874 (2)0.0607 (14)
H100.60030.70420.31040.073*
C110.7122 (12)0.6153 (10)0.2466 (2)0.0596 (14)
C120.6622 (12)0.4629 (10)0.2110 (2)0.0615 (15)
C130.4843 (14)0.2997 (13)0.2195 (2)0.0735 (18)
H130.44820.19890.19590.088*
C140.3589 (14)0.2784 (12)0.2605 (2)0.0708 (18)
H140.24790.16160.26510.085*
C150.9056 (16)0.7977 (11)0.2413 (3)0.081 (2)
H15A0.83930.89660.21770.097*
H15B1.07030.73980.23210.097*
H15C0.93010.87280.27050.097*
C160.7892 (12)0.4666 (10)0.1647 (2)0.0614 (15)
H160.91320.58770.16400.074*
C170.6042 (12)0.4788 (9)0.1233 (2)0.0564 (13)
C180.4134 (14)0.6369 (11)0.1111 (2)0.0677 (16)
H180.39300.75950.12960.081*
C190.2579 (14)0.6036 (12)0.0709 (3)0.0724 (17)
H190.13000.70480.06220.087*
C200.2904 (16)0.4215 (13)0.0435 (3)0.0796 (19)
H200.18550.40440.01640.095*
C210.4750 (15)0.2636 (11)0.0555 (2)0.0726 (18)
H210.49310.14010.03730.087*
C220.6318 (12)0.2983 (10)0.0958 (2)0.0614 (15)
C230.8346 (14)0.1621 (11)0.1170 (3)0.0738 (18)
N10.2714 (11)0.4265 (9)0.33723 (18)0.0672 (14)
O10.3282 (13)0.2054 (8)0.4116 (2)0.0952 (17)
O20.2655 (10)0.0486 (7)0.35637 (17)0.0762 (13)
O30.9179 (13)0.0058 (9)0.1046 (2)0.1006 (18)
O40.9290 (9)0.2620 (8)0.15717 (18)0.0771 (13)
H10.315 (16)0.515 (11)0.360 (2)0.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.088 (5)0.055 (4)0.074 (4)0.008 (3)0.010 (3)0.000 (3)
C20.070 (4)0.053 (3)0.062 (3)0.004 (3)0.004 (3)0.000 (3)
C30.095 (5)0.065 (4)0.070 (4)0.004 (4)0.010 (4)0.011 (3)
C40.097 (5)0.077 (5)0.066 (4)0.007 (4)0.021 (4)0.008 (3)
C50.074 (4)0.077 (4)0.071 (4)0.018 (3)0.012 (3)0.001 (3)
C60.071 (4)0.063 (4)0.069 (4)0.015 (3)0.009 (3)0.001 (3)
C70.060 (3)0.060 (3)0.063 (3)0.001 (3)0.004 (3)0.003 (3)
C80.071 (4)0.057 (3)0.059 (3)0.001 (3)0.007 (3)0.003 (3)
C90.072 (4)0.057 (4)0.057 (3)0.001 (3)0.007 (3)0.002 (2)
C100.071 (4)0.049 (3)0.062 (3)0.009 (3)0.002 (3)0.004 (2)
C110.060 (3)0.054 (3)0.065 (3)0.001 (3)0.004 (3)0.003 (3)
C120.058 (3)0.060 (3)0.067 (4)0.005 (3)0.011 (3)0.001 (3)
C130.077 (4)0.079 (5)0.065 (4)0.020 (4)0.016 (3)0.017 (3)
C140.082 (4)0.066 (4)0.065 (4)0.029 (3)0.011 (3)0.008 (3)
C150.092 (5)0.066 (4)0.084 (5)0.024 (4)0.013 (4)0.001 (4)
C160.058 (3)0.059 (3)0.068 (4)0.001 (3)0.008 (3)0.002 (3)
C170.066 (3)0.046 (3)0.059 (3)0.002 (3)0.022 (3)0.001 (2)
C180.082 (4)0.061 (3)0.062 (4)0.013 (3)0.014 (3)0.001 (3)
C190.072 (4)0.070 (4)0.076 (4)0.013 (3)0.014 (3)0.005 (3)
C200.078 (4)0.093 (5)0.068 (4)0.003 (4)0.009 (3)0.006 (4)
C210.083 (4)0.067 (4)0.069 (4)0.007 (3)0.017 (3)0.011 (3)
C220.065 (4)0.051 (3)0.070 (4)0.003 (3)0.016 (3)0.006 (3)
C230.078 (4)0.055 (3)0.091 (5)0.005 (3)0.025 (4)0.002 (3)
N10.083 (4)0.059 (3)0.060 (3)0.010 (3)0.012 (3)0.005 (2)
O10.116 (4)0.063 (3)0.106 (4)0.023 (3)0.008 (3)0.004 (3)
O20.091 (3)0.060 (3)0.079 (3)0.006 (2)0.021 (2)0.008 (2)
O30.108 (4)0.073 (3)0.123 (5)0.022 (3)0.026 (3)0.006 (3)
O40.067 (3)0.083 (3)0.082 (3)0.019 (2)0.009 (2)0.000 (2)
Geometric parameters (Å, º) top
C1—O11.210 (8)C12—C161.499 (8)
C1—O21.347 (8)C13—C141.366 (9)
C1—C21.468 (9)C13—H130.9300
C2—C71.380 (9)C14—H140.9300
C2—C31.388 (9)C15—H15A0.9600
C3—C41.391 (10)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—C51.395 (10)C16—O41.472 (8)
C4—H40.9300C16—C171.483 (9)
C5—C61.371 (9)C16—H160.9800
C5—H50.9300C17—C221.374 (8)
C6—C71.373 (9)C17—C181.412 (9)
C6—H60.9300C18—C191.384 (10)
C7—C81.498 (9)C18—H180.9300
C8—N11.414 (8)C19—C201.385 (10)
C8—O21.481 (8)C19—H190.9300
C8—H80.9800C20—C211.388 (11)
C9—C101.384 (9)C20—H200.9300
C9—C141.387 (9)C21—C221.392 (10)
C9—N11.389 (8)C21—H210.9300
C10—C111.391 (9)C22—C231.446 (10)
C10—H100.9300C23—O31.180 (8)
C11—C121.401 (9)C23—O41.372 (10)
C11—C151.510 (9)N1—H10.88 (7)
C12—C131.385 (10)
O1—C1—O2122.0 (7)C13—C14—C9119.3 (6)
O1—C1—C2129.2 (7)C13—C14—H14120.4
O2—C1—C2108.8 (5)C9—C14—H14120.4
C7—C2—C3122.0 (6)C11—C15—H15A109.5
C7—C2—C1108.3 (6)C11—C15—H15B109.5
C3—C2—C1129.6 (6)H15A—C15—H15B109.5
C2—C3—C4116.8 (6)C11—C15—H15C109.5
C2—C3—H3121.6H15A—C15—H15C109.5
C4—C3—H3121.6H15B—C15—H15C109.5
C3—C4—C5120.5 (7)O4—C16—C17102.9 (5)
C3—C4—H4119.8O4—C16—C12110.3 (5)
C5—C4—H4119.8C17—C16—C12114.9 (5)
C6—C5—C4121.8 (7)O4—C16—H16109.5
C6—C5—H5119.1C17—C16—H16109.5
C4—C5—H5119.1C12—C16—H16109.5
C5—C6—C7117.9 (6)C22—C17—C18120.5 (6)
C5—C6—H6121.1C22—C17—C16109.7 (5)
C7—C6—H6121.1C18—C17—C16129.8 (5)
C6—C7—C2121.0 (6)C19—C18—C17117.8 (6)
C6—C7—C8130.1 (6)C19—C18—H18121.1
C2—C7—C8108.9 (5)C17—C18—H18121.1
N1—C8—O2111.8 (5)C18—C19—C20120.8 (7)
N1—C8—C7114.1 (5)C18—C19—H19119.6
O2—C8—C7103.3 (5)C20—C19—H19119.6
N1—C8—H8109.1C19—C20—C21121.9 (7)
O2—C8—H8109.1C19—C20—H20119.1
C7—C8—H8109.1C21—C20—H20119.1
C10—C9—C14118.0 (6)C20—C21—C22117.1 (6)
C10—C9—N1119.5 (5)C20—C21—H21121.4
C14—C9—N1122.5 (6)C22—C21—H21121.4
C9—C10—C11123.0 (6)C17—C22—C21121.9 (6)
C9—C10—H10118.5C17—C22—C23108.8 (6)
C11—C10—H10118.5C21—C22—C23129.3 (6)
C10—C11—C12118.4 (6)O3—C23—O4121.8 (7)
C10—C11—C15119.8 (6)O3—C23—C22130.3 (8)
C12—C11—C15121.8 (6)O4—C23—C22107.9 (6)
C13—C12—C11117.6 (6)C9—N1—C8122.2 (5)
C13—C12—C16118.5 (6)C9—N1—H1121 (6)
C11—C12—C16123.9 (6)C8—N1—H1115 (6)
C14—C13—C12123.7 (6)C1—O2—C8110.6 (5)
C14—C13—H13118.2C23—O4—C16110.7 (5)
C12—C13—H13118.2
O1—C1—C2—C7178.5 (8)C13—C12—C16—C1757.8 (8)
O2—C1—C2—C70.3 (8)C11—C12—C16—C17122.1 (6)
O1—C1—C2—C33.9 (13)O4—C16—C17—C221.2 (6)
O2—C1—C2—C3177.9 (7)C12—C16—C17—C22118.6 (6)
C7—C2—C3—C41.7 (11)O4—C16—C17—C18178.7 (6)
C1—C2—C3—C4179.0 (7)C12—C16—C17—C1858.9 (9)
C2—C3—C4—C50.3 (11)C22—C17—C18—C190.1 (9)
C3—C4—C5—C60.7 (12)C16—C17—C18—C19177.4 (6)
C4—C5—C6—C71.0 (11)C17—C18—C19—C200.4 (10)
C5—C6—C7—C23.0 (10)C18—C19—C20—C211.2 (11)
C5—C6—C7—C8176.4 (7)C19—C20—C21—C221.5 (11)
C3—C2—C7—C63.4 (10)C18—C17—C22—C210.1 (9)
C1—C2—C7—C6178.8 (6)C16—C17—C22—C21177.6 (6)
C3—C2—C7—C8176.1 (7)C18—C17—C22—C23178.5 (6)
C1—C2—C7—C81.7 (7)C16—C17—C22—C230.7 (7)
C6—C7—C8—N156.1 (9)C20—C21—C22—C170.9 (10)
C2—C7—C8—N1124.5 (6)C20—C21—C22—C23178.9 (7)
C6—C7—C8—O2177.6 (7)C17—C22—C23—O3180.0 (7)
C2—C7—C8—O22.9 (6)C21—C22—C23—O31.9 (12)
C14—C9—C10—C110.8 (9)C17—C22—C23—O40.2 (7)
N1—C9—C10—C11179.1 (6)C21—C22—C23—O4178.3 (7)
C9—C10—C11—C123.2 (9)C10—C9—N1—C8173.4 (6)
C9—C10—C11—C15178.2 (6)C14—C9—N1—C86.5 (10)
C10—C11—C12—C132.4 (9)O2—C8—N1—C965.6 (8)
C15—C11—C12—C13179.1 (7)C7—C8—N1—C9177.6 (6)
C10—C11—C12—C16177.6 (6)O1—C1—O2—C8179.4 (7)
C15—C11—C12—C161.0 (10)C2—C1—O2—C82.2 (7)
C11—C12—C13—C140.8 (11)N1—C8—O2—C1126.3 (6)
C16—C12—C13—C14179.2 (7)C7—C8—O2—C13.2 (7)
C12—C13—C14—C93.3 (12)O3—C23—O4—C16179.2 (6)
C10—C9—C14—C132.5 (10)C22—C23—O4—C161.0 (7)
N1—C9—C14—C13177.7 (7)C17—C16—O4—C231.4 (6)
C13—C12—C16—O457.8 (8)C12—C16—O4—C23121.6 (6)
C11—C12—C16—O4122.2 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (7)2.26 (6)3.118 (7)164 (7)
C5—H5···O1ii0.932.623.256 (9)126
C19—H19···O3ii0.932.443.147 (9)133
C15—H15b···Cg1iii0.963.003.861 (8)150
C4—H4···Cg2iv0.933.183.912 (9)137
Symmetry codes: (i) x, y+1, z; (ii) x1, y+1, z; (iii) x+1, y, z; (iv) x1, y+1, z+1/2.
 

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