3-(4-Methoxy­anilino)isobenzofuran-1(3H)-one

Crystals of the title compound, C₁₅H₁₃NO₃, are stabilized by N—H...O inter­molecular hydrogen bonds and two C—H...π inter­molecular inter­actions. The N—H...O hydrogen bonds generate an R₂²(12) ring motif and the phthalide part of the mol­ecule is planar. The dihedral angle between the phthalide group and the benzene ring is 71.18 (5)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  CG2     ..       3.18 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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, 1990); 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).

3-(4-Methoxyanilino)isobenzofuran-1(3H)-one

Crystal data

C15H13NO3	F(000) = 536
Mr = 255.26	Dx = 1.382 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16415 reflections
a = 10.5814 (8) Å	θ = 2.0–28.0°
b = 8.1613 (4) Å	µ = 0.10 mm^−1
c = 15.2896 (11) Å	T = 296 K
β = 111.656 (5)°	Prism, brown
V = 1227.18 (14) Å^3	0.61 × 0.53 × 0.38 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	2406 independent reflections
Plane graphite monochromator	1968 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	Rint = 0.059
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −13→13
Tmin = 0.940, Tmax = 0.969	k = −10→10
16415 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.0742P] where P = (Fo^2 + 2Fc^2)/3
2406 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.17 e Å^−3
1 restraint	Δρmin = −0.15 e Å^−3

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	0.59079 (12)	0.34343 (15)	0.47793 (8)	0.0468 (3)
C2	0.56682 (12)	0.26701 (14)	0.55781 (8)	0.0445 (3)
C3	0.64506 (13)	0.26920 (16)	0.65308 (9)	0.0532 (3)
H3	0.7287	0.3223	0.6760	0.064*
C4	0.59452 (14)	0.18987 (17)	0.71267 (9)	0.0567 (3)
H4	0.6449	0.1890	0.7770	0.068*
C5	0.46968 (14)	0.11138 (17)	0.67826 (9)	0.0549 (3)
H5	0.4376	0.0592	0.7201	0.066*
C6	0.39179 (13)	0.10895 (16)	0.58324 (9)	0.0500 (3)
H6	0.3083	0.0556	0.5602	0.060*
C7	0.44278 (11)	0.18884 (14)	0.52365 (8)	0.0432 (3)
C8	0.38067 (12)	0.20930 (14)	0.41905 (8)	0.0450 (3)
H8	0.3718	0.1017	0.3889	0.054*
C9	0.17154 (11)	0.30145 (14)	0.29229 (8)	0.0424 (3)
C10	0.05546 (12)	0.39864 (15)	0.26759 (9)	0.0485 (3)
H10	0.0364	0.4551	0.3141	0.058*
C11	−0.03107 (13)	0.41224 (16)	0.17553 (9)	0.0514 (3)
H11	−0.1079	0.4781	0.1604	0.062*
C12	−0.00538 (12)	0.32888 (14)	0.10478 (8)	0.0466 (3)
C13	0.10887 (12)	0.23202 (15)	0.12817 (9)	0.0480 (3)
H13	0.1271	0.1750	0.0815	0.058*
C14	0.19699 (12)	0.21920 (15)	0.22129 (8)	0.0473 (3)
H14	0.2744	0.1543	0.2362	0.057*
C15	−0.07303 (16)	0.2737 (2)	−0.05885 (10)	0.0657 (4)
H15A	−0.0726	0.1575	−0.0492	0.079*
H15B	0.0134	0.3072	−0.0599	0.079*
H15C	−0.1436	0.3012	−0.1177	0.079*
N1	0.25319 (10)	0.28614 (13)	0.38839 (7)	0.0476 (3)
O1	0.68406 (9)	0.42791 (12)	0.47754 (7)	0.0599 (3)
O2	0.48491 (8)	0.30731 (11)	0.39805 (6)	0.0516 (2)
O3	−0.09703 (9)	0.35515 (12)	0.01513 (6)	0.0600 (3)
H1	0.2500 (14)	0.3707 (18)	0.4243 (10)	0.058 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0469 (6)	0.0438 (6)	0.0522 (7)	0.0062 (5)	0.0212 (5)	−0.0040 (5)
C2	0.0452 (6)	0.0427 (6)	0.0442 (6)	0.0063 (5)	0.0149 (5)	−0.0042 (5)
C3	0.0489 (7)	0.0553 (7)	0.0491 (7)	0.0029 (5)	0.0106 (5)	−0.0080 (6)
C4	0.0617 (8)	0.0636 (8)	0.0388 (6)	0.0097 (6)	0.0116 (6)	−0.0041 (6)
C5	0.0628 (8)	0.0591 (8)	0.0461 (7)	0.0097 (6)	0.0240 (6)	0.0041 (6)
C6	0.0479 (6)	0.0523 (7)	0.0494 (7)	0.0027 (5)	0.0176 (5)	0.0007 (5)
C7	0.0448 (6)	0.0428 (6)	0.0407 (6)	0.0067 (5)	0.0142 (5)	−0.0022 (5)
C8	0.0472 (6)	0.0446 (6)	0.0417 (6)	0.0014 (5)	0.0144 (5)	−0.0015 (5)
C9	0.0426 (6)	0.0417 (6)	0.0420 (6)	−0.0021 (5)	0.0146 (5)	0.0008 (5)
C10	0.0502 (6)	0.0474 (6)	0.0491 (7)	0.0054 (5)	0.0195 (5)	−0.0004 (5)
C11	0.0453 (6)	0.0513 (7)	0.0551 (8)	0.0079 (5)	0.0156 (6)	0.0046 (5)
C12	0.0445 (6)	0.0453 (6)	0.0449 (6)	−0.0045 (5)	0.0107 (5)	0.0041 (5)
C13	0.0513 (7)	0.0486 (6)	0.0444 (6)	−0.0022 (5)	0.0182 (5)	−0.0020 (5)
C14	0.0449 (6)	0.0494 (6)	0.0469 (7)	0.0063 (5)	0.0162 (5)	0.0016 (5)
C15	0.0692 (9)	0.0743 (9)	0.0451 (7)	−0.0108 (7)	0.0113 (6)	−0.0016 (6)
N1	0.0479 (6)	0.0505 (6)	0.0406 (5)	0.0071 (4)	0.0119 (4)	−0.0030 (4)
O1	0.0574 (5)	0.0577 (5)	0.0714 (6)	−0.0036 (4)	0.0317 (5)	−0.0047 (4)
O2	0.0529 (5)	0.0599 (5)	0.0431 (5)	0.0020 (4)	0.0189 (4)	0.0014 (4)
O3	0.0545 (5)	0.0686 (6)	0.0456 (5)	0.0024 (4)	0.0053 (4)	0.0025 (4)

Geometric parameters (Å, º)

C1—O1	1.2056 (15)	C9—C14	1.3847 (16)
C1—O2	1.3505 (14)	C9—C10	1.3921 (16)
C1—C2	1.4744 (17)	C9—N1	1.4085 (15)
C2—C7	1.3771 (17)	C10—C11	1.3714 (17)
C2—C3	1.3848 (17)	C10—H10	0.9300
C3—C4	1.3766 (19)	C11—C12	1.3870 (18)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.385 (2)	C12—O3	1.3727 (14)
C4—H4	0.9300	C12—C13	1.3766 (17)
C5—C6	1.3809 (17)	C13—C14	1.3884 (17)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.3816 (17)	C14—H14	0.9300
C6—H6	0.9300	C15—O3	1.4133 (18)
C7—C8	1.4974 (16)	C15—H15A	0.9600
C8—N1	1.4022 (15)	C15—H15B	0.9600
C8—O2	1.4902 (14)	C15—H15C	0.9600
C8—H8	0.9800	N1—H1	0.891 (15)
O1—C1—O2	121.86 (11)	C14—C9—N1	123.57 (10)
O1—C1—C2	129.60 (12)	C10—C9—N1	118.27 (10)
O2—C1—C2	108.53 (10)	C11—C10—C9	120.84 (11)
C7—C2—C3	121.40 (12)	C11—C10—H10	119.6
C7—C2—C1	108.25 (10)	C9—C10—H10	119.6
C3—C2—C1	130.32 (12)	C10—C11—C12	120.80 (11)
C4—C3—C2	117.56 (12)	C10—C11—H11	119.6
C4—C3—H3	121.2	C12—C11—H11	119.6
C2—C3—H3	121.2	O3—C12—C13	125.32 (11)
C3—C4—C5	121.00 (12)	O3—C12—C11	115.63 (11)
C3—C4—H4	119.5	C13—C12—C11	119.02 (11)
C5—C4—H4	119.5	C12—C13—C14	120.18 (11)
C6—C5—C4	121.43 (12)	C12—C13—H13	119.9
C6—C5—H5	119.3	C14—C13—H13	119.9
C4—C5—H5	119.3	C9—C14—C13	121.07 (11)
C5—C6—C7	117.41 (12)	C9—C14—H14	119.5
C5—C6—H6	121.3	C13—C14—H14	119.5
C7—C6—H6	121.3	O3—C15—H15A	109.5
C2—C7—C6	121.20 (11)	O3—C15—H15B	109.5
C2—C7—C8	109.55 (10)	H15A—C15—H15B	109.5
C6—C7—C8	129.25 (11)	O3—C15—H15C	109.5
N1—C8—O2	112.65 (9)	H15A—C15—H15C	109.5
N1—C8—C7	113.32 (10)	H15B—C15—H15C	109.5
O2—C8—C7	102.82 (9)	C8—N1—C9	122.18 (10)
N1—C8—H8	109.3	C8—N1—H1	113.0 (9)
O2—C8—H8	109.3	C9—N1—H1	115.3 (9)
C7—C8—H8	109.3	C1—O2—C8	110.82 (9)
C14—C9—C10	118.09 (11)	C12—O3—C15	117.15 (11)
O1—C1—C2—C7	176.96 (12)	N1—C9—C10—C11	−177.09 (11)
O2—C1—C2—C7	−1.64 (13)	C9—C10—C11—C12	0.28 (19)
O1—C1—C2—C3	−1.1 (2)	C10—C11—C12—O3	−178.37 (11)
O2—C1—C2—C3	−179.72 (11)	C10—C11—C12—C13	−0.14 (18)
C7—C2—C3—C4	0.16 (17)	O3—C12—C13—C14	177.72 (11)
C1—C2—C3—C4	178.04 (12)	C11—C12—C13—C14	−0.33 (18)
C2—C3—C4—C5	−0.21 (19)	C10—C9—C14—C13	−0.52 (17)
C3—C4—C5—C6	0.3 (2)	N1—C9—C14—C13	176.45 (11)
C4—C5—C6—C7	−0.39 (19)	C12—C13—C14—C9	0.67 (18)
C3—C2—C7—C6	−0.24 (17)	O2—C8—N1—C9	70.60 (14)
C1—C2—C7—C6	−178.53 (10)	C7—C8—N1—C9	−173.19 (10)
C3—C2—C7—C8	178.97 (10)	C14—C9—N1—C8	11.70 (18)
C1—C2—C7—C8	0.68 (12)	C10—C9—N1—C8	−171.34 (11)
C5—C6—C7—C2	0.34 (17)	O1—C1—O2—C8	−176.80 (10)
C5—C6—C7—C8	−178.69 (12)	C2—C1—O2—C8	1.93 (12)
C2—C7—C8—N1	−121.47 (11)	N1—C8—O2—C1	120.87 (11)
C6—C7—C8—N1	57.65 (16)	C7—C8—O2—C1	−1.47 (11)
C2—C7—C8—O2	0.41 (12)	C13—C12—O3—C15	1.13 (18)
C6—C7—C8—O2	179.54 (11)	C11—C12—O3—C15	179.23 (12)
C14—C9—C10—C11	0.05 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.891 (15)	2.160 (15)	3.0141 (14)	160.4 (12)
C8—H8···Cg1^ii	0.98	2.66	3.534 (1)	148
C10—H10···Cg2^iii	0.93	3.18	3.812 (1)	127

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