[2-Methyl-4-(3-oxo-1,3-dihydro­isobenzofuran-1-ylamino)phen­yl]isobenzofuran-1(3H)-one

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.

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

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Computing details

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

Crystal data

C23H17NO4	F(000) = 388
Mr = 371.38	Dx = 1.370 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 7767 reflections
a = 5.1039 (3) Å	θ = 1.4–25.0°
b = 6.1761 (6) Å	µ = 0.09 mm^−1
c = 28.5758 (18) Å	T = 296 K
β = 92.444 (5)°	Prism, light brown
V = 899.95 (12) Å^3	0.54 × 0.30 × 0.12 mm
Z = 2

Data collection

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 monochromator	Rint = 0.102
Detector resolution: 6.67 pixels mm^-1	θmax = 25.1°, θmin = 1.4°
ω scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
Tmin = 0.963, Tmax = 0.990	l = −33→33
8708 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.1066P)^2 + 0.2251P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
1592 reflections	Δρmax = 0.27 e Å^−3
258 parameters	Δρmin = −0.19 e Å^−3
3 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2238 (15)	−0.0386 (11)	0.3986 (3)	0.0722 (17)
C2	0.0468 (13)	0.1036 (9)	0.4237 (2)	0.0616 (14)
C3	−0.0572 (17)	0.0779 (11)	0.4675 (3)	0.0764 (18)
H3	−0.0166	−0.0418	0.4861	0.092*
C4	−0.2249 (17)	0.2397 (11)	0.4820 (3)	0.080 (2)
H4	−0.2999	0.2288	0.5110	0.096*
C5	−0.2815 (15)	0.4182 (12)	0.4534 (2)	0.0738 (18)
H5	−0.3926	0.5253	0.4639	0.089*
C6	−0.1776 (13)	0.4399 (11)	0.4102 (2)	0.0673 (16)
H6	−0.2145	0.5607	0.3916	0.081*
C7	−0.0174 (12)	0.2778 (10)	0.3952 (2)	0.0606 (14)
C8	0.1114 (13)	0.2502 (10)	0.3495 (2)	0.0623 (15)
H8	−0.0239	0.2272	0.3246	0.075*
C9	0.3990 (13)	0.4331 (10)	0.2953 (2)	0.0620 (15)
C10	0.5739 (13)	0.5989 (10)	0.2874 (2)	0.0607 (14)
H10	0.6003	0.7042	0.3104	0.073*
C11	0.7122 (12)	0.6153 (10)	0.2466 (2)	0.0596 (14)
C12	0.6622 (12)	0.4629 (10)	0.2110 (2)	0.0615 (15)
C13	0.4843 (14)	0.2997 (13)	0.2195 (2)	0.0735 (18)
H13	0.4482	0.1989	0.1959	0.088*
C14	0.3589 (14)	0.2784 (12)	0.2605 (2)	0.0708 (18)
H14	0.2479	0.1616	0.2651	0.085*
C15	0.9056 (16)	0.7977 (11)	0.2413 (3)	0.081 (2)
H15A	0.8393	0.8966	0.2177	0.097*
H15B	1.0703	0.7398	0.2321	0.097*
H15C	0.9301	0.8728	0.2705	0.097*
C16	0.7892 (12)	0.4666 (10)	0.1647 (2)	0.0614 (15)
H16	0.9132	0.5877	0.1640	0.074*
C17	0.6042 (12)	0.4788 (9)	0.1233 (2)	0.0564 (13)
C18	0.4134 (14)	0.6369 (11)	0.1111 (2)	0.0677 (16)
H18	0.3930	0.7595	0.1296	0.081*
C19	0.2579 (14)	0.6036 (12)	0.0709 (3)	0.0724 (17)
H19	0.1300	0.7048	0.0622	0.087*
C20	0.2904 (16)	0.4215 (13)	0.0435 (3)	0.0796 (19)
H20	0.1855	0.4044	0.0164	0.095*
C21	0.4750 (15)	0.2636 (11)	0.0555 (2)	0.0726 (18)
H21	0.4931	0.1401	0.0373	0.087*
C22	0.6318 (12)	0.2983 (10)	0.0958 (2)	0.0614 (15)
C23	0.8346 (14)	0.1621 (11)	0.1170 (3)	0.0738 (18)
N1	0.2714 (11)	0.4265 (9)	0.33723 (18)	0.0672 (14)
O1	0.3282 (13)	−0.2054 (8)	0.4116 (2)	0.0952 (17)
O2	0.2655 (10)	0.0486 (7)	0.35637 (17)	0.0762 (13)
O3	0.9179 (13)	−0.0058 (9)	0.1046 (2)	0.1006 (18)
O4	0.9290 (9)	0.2620 (8)	0.15717 (18)	0.0771 (13)
H1	0.315 (16)	0.515 (11)	0.360 (2)	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.088 (5)	0.055 (4)	0.074 (4)	0.008 (3)	0.010 (3)	0.000 (3)
C2	0.070 (4)	0.053 (3)	0.062 (3)	0.004 (3)	0.004 (3)	0.000 (3)
C3	0.095 (5)	0.065 (4)	0.070 (4)	0.004 (4)	0.010 (4)	0.011 (3)
C4	0.097 (5)	0.077 (5)	0.066 (4)	0.007 (4)	0.021 (4)	0.008 (3)
C5	0.074 (4)	0.077 (4)	0.071 (4)	0.018 (3)	0.012 (3)	−0.001 (3)
C6	0.071 (4)	0.063 (4)	0.069 (4)	0.015 (3)	0.009 (3)	0.001 (3)
C7	0.060 (3)	0.060 (3)	0.063 (3)	−0.001 (3)	0.004 (3)	0.003 (3)
C8	0.071 (4)	0.057 (3)	0.059 (3)	−0.001 (3)	0.007 (3)	−0.003 (3)
C9	0.072 (4)	0.057 (4)	0.057 (3)	−0.001 (3)	0.007 (3)	−0.002 (2)
C10	0.071 (4)	0.049 (3)	0.062 (3)	−0.009 (3)	−0.002 (3)	−0.004 (2)
C11	0.060 (3)	0.054 (3)	0.065 (3)	0.001 (3)	0.004 (3)	0.003 (3)
C12	0.058 (3)	0.060 (3)	0.067 (4)	−0.005 (3)	0.011 (3)	−0.001 (3)
C13	0.077 (4)	0.079 (5)	0.065 (4)	−0.020 (4)	0.016 (3)	−0.017 (3)
C14	0.082 (4)	0.066 (4)	0.065 (4)	−0.029 (3)	0.011 (3)	−0.008 (3)
C15	0.092 (5)	0.066 (4)	0.084 (5)	−0.024 (4)	0.013 (4)	0.001 (4)
C16	0.058 (3)	0.059 (3)	0.068 (4)	−0.001 (3)	0.008 (3)	−0.002 (3)
C17	0.066 (3)	0.046 (3)	0.059 (3)	−0.002 (3)	0.022 (3)	0.001 (2)
C18	0.082 (4)	0.061 (3)	0.062 (4)	0.013 (3)	0.014 (3)	0.001 (3)
C19	0.072 (4)	0.070 (4)	0.076 (4)	0.013 (3)	0.014 (3)	0.005 (3)
C20	0.078 (4)	0.093 (5)	0.068 (4)	0.003 (4)	0.009 (3)	−0.006 (4)
C21	0.083 (4)	0.067 (4)	0.069 (4)	−0.007 (3)	0.017 (3)	−0.011 (3)
C22	0.065 (4)	0.051 (3)	0.070 (4)	0.003 (3)	0.016 (3)	−0.006 (3)
C23	0.078 (4)	0.055 (3)	0.091 (5)	0.005 (3)	0.025 (4)	0.002 (3)
N1	0.083 (4)	0.059 (3)	0.060 (3)	−0.010 (3)	0.012 (3)	−0.005 (2)
O1	0.116 (4)	0.063 (3)	0.106 (4)	0.023 (3)	0.008 (3)	0.004 (3)
O2	0.091 (3)	0.060 (3)	0.079 (3)	0.006 (2)	0.021 (2)	−0.008 (2)
O3	0.108 (4)	0.073 (3)	0.123 (5)	0.022 (3)	0.026 (3)	−0.006 (3)
O4	0.067 (3)	0.083 (3)	0.082 (3)	0.019 (2)	0.009 (2)	0.000 (2)

Geometric parameters (Å, º)

C1—O1	1.210 (8)	C12—C16	1.499 (8)
C1—O2	1.347 (8)	C13—C14	1.366 (9)
C1—C2	1.468 (9)	C13—H13	0.9300
C2—C7	1.380 (9)	C14—H14	0.9300
C2—C3	1.388 (9)	C15—H15A	0.9600
C3—C4	1.391 (10)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.395 (10)	C16—O4	1.472 (8)
C4—H4	0.9300	C16—C17	1.483 (9)
C5—C6	1.371 (9)	C16—H16	0.9800
C5—H5	0.9300	C17—C22	1.374 (8)
C6—C7	1.373 (9)	C17—C18	1.412 (9)
C6—H6	0.9300	C18—C19	1.384 (10)
C7—C8	1.498 (9)	C18—H18	0.9300
C8—N1	1.414 (8)	C19—C20	1.385 (10)
C8—O2	1.481 (8)	C19—H19	0.9300
C8—H8	0.9800	C20—C21	1.388 (11)
C9—C10	1.384 (9)	C20—H20	0.9300
C9—C14	1.387 (9)	C21—C22	1.392 (10)
C9—N1	1.389 (8)	C21—H21	0.9300
C10—C11	1.391 (9)	C22—C23	1.446 (10)
C10—H10	0.9300	C23—O3	1.180 (8)
C11—C12	1.401 (9)	C23—O4	1.372 (10)
C11—C15	1.510 (9)	N1—H1	0.88 (7)
C12—C13	1.385 (10)
O1—C1—O2	122.0 (7)	C13—C14—C9	119.3 (6)
O1—C1—C2	129.2 (7)	C13—C14—H14	120.4
O2—C1—C2	108.8 (5)	C9—C14—H14	120.4
C7—C2—C3	122.0 (6)	C11—C15—H15A	109.5
C7—C2—C1	108.3 (6)	C11—C15—H15B	109.5
C3—C2—C1	129.6 (6)	H15A—C15—H15B	109.5
C2—C3—C4	116.8 (6)	C11—C15—H15C	109.5
C2—C3—H3	121.6	H15A—C15—H15C	109.5
C4—C3—H3	121.6	H15B—C15—H15C	109.5
C3—C4—C5	120.5 (7)	O4—C16—C17	102.9 (5)
C3—C4—H4	119.8	O4—C16—C12	110.3 (5)
C5—C4—H4	119.8	C17—C16—C12	114.9 (5)
C6—C5—C4	121.8 (7)	O4—C16—H16	109.5
C6—C5—H5	119.1	C17—C16—H16	109.5
C4—C5—H5	119.1	C12—C16—H16	109.5
C5—C6—C7	117.9 (6)	C22—C17—C18	120.5 (6)
C5—C6—H6	121.1	C22—C17—C16	109.7 (5)
C7—C6—H6	121.1	C18—C17—C16	129.8 (5)
C6—C7—C2	121.0 (6)	C19—C18—C17	117.8 (6)
C6—C7—C8	130.1 (6)	C19—C18—H18	121.1
C2—C7—C8	108.9 (5)	C17—C18—H18	121.1
N1—C8—O2	111.8 (5)	C18—C19—C20	120.8 (7)
N1—C8—C7	114.1 (5)	C18—C19—H19	119.6
O2—C8—C7	103.3 (5)	C20—C19—H19	119.6
N1—C8—H8	109.1	C19—C20—C21	121.9 (7)
O2—C8—H8	109.1	C19—C20—H20	119.1
C7—C8—H8	109.1	C21—C20—H20	119.1
C10—C9—C14	118.0 (6)	C20—C21—C22	117.1 (6)
C10—C9—N1	119.5 (5)	C20—C21—H21	121.4
C14—C9—N1	122.5 (6)	C22—C21—H21	121.4
C9—C10—C11	123.0 (6)	C17—C22—C21	121.9 (6)
C9—C10—H10	118.5	C17—C22—C23	108.8 (6)
C11—C10—H10	118.5	C21—C22—C23	129.3 (6)
C10—C11—C12	118.4 (6)	O3—C23—O4	121.8 (7)
C10—C11—C15	119.8 (6)	O3—C23—C22	130.3 (8)
C12—C11—C15	121.8 (6)	O4—C23—C22	107.9 (6)
C13—C12—C11	117.6 (6)	C9—N1—C8	122.2 (5)
C13—C12—C16	118.5 (6)	C9—N1—H1	121 (6)
C11—C12—C16	123.9 (6)	C8—N1—H1	115 (6)
C14—C13—C12	123.7 (6)	C1—O2—C8	110.6 (5)
C14—C13—H13	118.2	C23—O4—C16	110.7 (5)
C12—C13—H13	118.2
O1—C1—C2—C7	178.5 (8)	C13—C12—C16—C17	57.8 (8)
O2—C1—C2—C7	0.3 (8)	C11—C12—C16—C17	−122.1 (6)
O1—C1—C2—C3	−3.9 (13)	O4—C16—C17—C22	1.2 (6)
O2—C1—C2—C3	177.9 (7)	C12—C16—C17—C22	−118.6 (6)
C7—C2—C3—C4	−1.7 (11)	O4—C16—C17—C18	178.7 (6)
C1—C2—C3—C4	−179.0 (7)	C12—C16—C17—C18	58.9 (9)
C2—C3—C4—C5	−0.3 (11)	C22—C17—C18—C19	−0.1 (9)
C3—C4—C5—C6	0.7 (12)	C16—C17—C18—C19	−177.4 (6)
C4—C5—C6—C7	1.0 (11)	C17—C18—C19—C20	−0.4 (10)
C5—C6—C7—C2	−3.0 (10)	C18—C19—C20—C21	1.2 (11)
C5—C6—C7—C8	176.4 (7)	C19—C20—C21—C22	−1.5 (11)
C3—C2—C7—C6	3.4 (10)	C18—C17—C22—C21	−0.1 (9)
C1—C2—C7—C6	−178.8 (6)	C16—C17—C22—C21	177.6 (6)
C3—C2—C7—C8	−176.1 (7)	C18—C17—C22—C23	−178.5 (6)
C1—C2—C7—C8	1.7 (7)	C16—C17—C22—C23	−0.7 (7)
C6—C7—C8—N1	56.1 (9)	C20—C21—C22—C17	0.9 (10)
C2—C7—C8—N1	−124.5 (6)	C20—C21—C22—C23	178.9 (7)
C6—C7—C8—O2	177.6 (7)	C17—C22—C23—O3	−180.0 (7)
C2—C7—C8—O2	−2.9 (6)	C21—C22—C23—O3	1.9 (12)
C14—C9—C10—C11	−0.8 (9)	C17—C22—C23—O4	−0.2 (7)
N1—C9—C10—C11	179.1 (6)	C21—C22—C23—O4	−178.3 (7)
C9—C10—C11—C12	3.2 (9)	C10—C9—N1—C8	−173.4 (6)
C9—C10—C11—C15	−178.2 (6)	C14—C9—N1—C8	6.5 (10)
C10—C11—C12—C13	−2.4 (9)	O2—C8—N1—C9	65.6 (8)
C15—C11—C12—C13	179.1 (7)	C7—C8—N1—C9	−177.6 (6)
C10—C11—C12—C16	177.6 (6)	O1—C1—O2—C8	179.4 (7)
C15—C11—C12—C16	−1.0 (10)	C2—C1—O2—C8	−2.2 (7)
C11—C12—C13—C14	−0.8 (11)	N1—C8—O2—C1	126.3 (6)
C16—C12—C13—C14	179.2 (7)	C7—C8—O2—C1	3.2 (7)
C12—C13—C14—C9	3.3 (12)	O3—C23—O4—C16	−179.2 (6)
C10—C9—C14—C13	−2.5 (10)	C22—C23—O4—C16	1.0 (7)
N1—C9—C14—C13	177.7 (7)	C17—C16—O4—C23	−1.4 (6)
C13—C12—C16—O4	−57.8 (8)	C12—C16—O4—C23	121.6 (6)
C11—C12—C16—O4	122.2 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88 (7)	2.26 (6)	3.118 (7)	164 (7)
C5—H5···O1^ii	0.93	2.62	3.256 (9)	126
C19—H19···O3^ii	0.93	2.44	3.147 (9)	133
C15—H15b···Cg1^iii	0.96	3.00	3.861 (8)	150
C4—H4···Cg2^iv	0.93	3.18	3.912 (9)	137

Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) x+1, y, z; (iv) x−1, −y+1, z+1/2.