3-(2-Methoxy­anilino)isobenzofuran-1(3H)-one

The title compound, C₁₅H₁₃NO₃, contains an intra­molecular N—H...O hydrogen bond and the packing is stabilized by N—H...O and C—H...O inter­molecular hydrogen bonds. The N—H...O hydrogen bonds generate S(5)[R₂²(12)]S(5) motifs and these motifs are bonded to each other by C—H...O inter­molecular hydrogen bonds. The phthalide group is planar, showing a dihedral angle of 63.26 (8)° with the benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.040
• wR factor = 0.100
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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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).

3-(2-Methoxyanilino)isobenzofuran-1(3H)-one

Crystal data

C15H13NO3	Z = 2
Mr = 255.26	F(000) = 268
Triclinic, P1	Dx = 1.382 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1259 (10) Å	Cell parameters from 8287 reflections
b = 8.2644 (11) Å	θ = 2.0–27.9°
c = 10.6641 (13) Å	µ = 0.10 mm^−1
α = 87.136 (11)°	T = 296 K
β = 78.29 (1)°	Prism, brown
γ = 61.155 (9)°	0.50 × 0.32 × 0.21 mm
V = 613.28 (15) Å^3

Data collection

Stoe IPDS-2 diffractometer	2399 independent reflections
Radiation source: fine-focus sealed tube	1774 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.8°
φ or ω scans?	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.970, Tmax = 0.986	l = −13→13
8287 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.0674P] where P = (Fo^2 + 2Fc^2)/3
2399 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.14 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	0.3741 (2)	0.2100 (2)	0.42760 (14)	0.0501 (4)
C2	0.5416 (2)	0.2166 (2)	0.45327 (13)	0.0456 (4)
C3	0.7183 (2)	0.1646 (2)	0.37368 (15)	0.0568 (4)
H3	0.7461	0.1172	0.2902	0.068*
C4	0.8510 (2)	0.1857 (2)	0.42263 (17)	0.0622 (5)
H4	0.9711	0.1524	0.3715	0.075*
C5	0.8085 (2)	0.2558 (2)	0.54710 (18)	0.0616 (4)
H5	0.9008	0.2688	0.5780	0.074*
C6	0.6323 (2)	0.3068 (2)	0.62651 (16)	0.0543 (4)
H6	0.6047	0.3531	0.7103	0.065*
C7	0.4985 (2)	0.2867 (2)	0.57705 (13)	0.0439 (3)
C8	0.2961 (2)	0.3346 (2)	0.63722 (14)	0.0470 (4)
H8	0.2200	0.4689	0.6547	0.056*
C9	0.0975 (2)	0.3046 (2)	0.83210 (13)	0.0466 (4)
C10	0.0926 (2)	0.2131 (2)	0.94528 (14)	0.0518 (4)
C11	−0.0770 (3)	0.2735 (3)	1.03430 (16)	0.0684 (5)
H11	−0.0797	0.2136	1.1102	0.082*
C12	−0.2439 (3)	0.4241 (3)	1.01046 (19)	0.0740 (6)
H12	−0.3578	0.4654	1.0710	0.089*
C13	−0.2417 (2)	0.5114 (3)	0.89925 (19)	0.0672 (5)
H13	−0.3542	0.6112	0.8835	0.081*
C14	−0.0722 (2)	0.4518 (2)	0.80942 (16)	0.0577 (4)
H14	−0.0719	0.5111	0.7330	0.069*
C15	0.2810 (3)	−0.0141 (3)	1.07813 (16)	0.0703 (5)
H15A	0.1896	−0.0581	1.1007	0.084*
H15B	0.2555	0.0772	1.1421	0.084*
H15C	0.4083	−0.1157	1.0733	0.084*
N1	0.27559 (19)	0.2480 (2)	0.75005 (12)	0.0498 (3)
O1	0.35503 (19)	0.15306 (19)	0.33259 (11)	0.0703 (4)
O2	0.23142 (15)	0.28049 (16)	0.53253 (10)	0.0546 (3)
O3	0.26565 (17)	0.06601 (18)	0.95719 (10)	0.0635 (3)
H1	0.367 (3)	0.140 (3)	0.7576 (16)	0.055 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0561 (9)	0.0513 (9)	0.0423 (8)	−0.0262 (8)	−0.0101 (7)	0.0093 (6)
C2	0.0484 (8)	0.0445 (8)	0.0423 (8)	−0.0232 (7)	−0.0051 (6)	0.0079 (6)
C3	0.0596 (10)	0.0542 (10)	0.0485 (8)	−0.0271 (8)	0.0043 (7)	0.0036 (7)
C4	0.0473 (9)	0.0574 (10)	0.0723 (11)	−0.0248 (8)	0.0053 (8)	0.0089 (8)
C5	0.0510 (10)	0.0625 (11)	0.0784 (12)	−0.0333 (9)	−0.0140 (9)	0.0118 (9)
C6	0.0553 (10)	0.0582 (10)	0.0545 (9)	−0.0320 (8)	−0.0097 (8)	0.0049 (7)
C7	0.0443 (8)	0.0430 (8)	0.0435 (8)	−0.0225 (7)	−0.0045 (6)	0.0069 (6)
C8	0.0459 (8)	0.0497 (9)	0.0440 (7)	−0.0241 (7)	−0.0037 (6)	0.0017 (6)
C9	0.0440 (8)	0.0582 (9)	0.0416 (7)	−0.0302 (7)	−0.0001 (6)	−0.0078 (6)
C10	0.0468 (9)	0.0725 (11)	0.0437 (8)	−0.0363 (9)	−0.0033 (7)	−0.0056 (7)
C11	0.0647 (12)	0.1075 (16)	0.0468 (9)	−0.0568 (12)	0.0037 (8)	−0.0067 (9)
C12	0.0463 (10)	0.1069 (16)	0.0679 (12)	−0.0423 (11)	0.0122 (9)	−0.0267 (11)
C13	0.0431 (9)	0.0772 (13)	0.0761 (12)	−0.0279 (9)	0.0012 (8)	−0.0182 (10)
C14	0.0480 (9)	0.0629 (11)	0.0602 (10)	−0.0268 (8)	−0.0054 (7)	−0.0046 (8)
C15	0.0841 (13)	0.0968 (15)	0.0492 (9)	−0.0572 (12)	−0.0203 (9)	0.0169 (9)
N1	0.0431 (7)	0.0530 (8)	0.0443 (7)	−0.0201 (7)	0.0015 (6)	0.0032 (6)
O1	0.0811 (9)	0.0860 (9)	0.0508 (7)	−0.0427 (8)	−0.0211 (6)	0.0028 (6)
O2	0.0487 (6)	0.0672 (7)	0.0504 (6)	−0.0303 (6)	−0.0099 (5)	0.0050 (5)
O3	0.0581 (7)	0.0845 (9)	0.0450 (6)	−0.0349 (7)	−0.0055 (5)	0.0132 (6)

Geometric parameters (Å, º)

C1—O1	1.2061 (19)	C9—C14	1.388 (2)
C1—O2	1.3502 (19)	C9—C10	1.396 (2)
C1—C2	1.468 (2)	C9—N1	1.3976 (19)
C2—C7	1.376 (2)	C10—O3	1.371 (2)
C2—C3	1.383 (2)	C10—C11	1.379 (2)
C3—C4	1.373 (2)	C11—C12	1.391 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.384 (3)	C12—C13	1.358 (3)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.381 (2)	C13—C14	1.384 (2)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.379 (2)	C14—H14	0.9300
C6—H6	0.9300	C15—O3	1.4204 (19)
C7—C8	1.498 (2)	C15—H15A	0.9600
C8—N1	1.3913 (19)	C15—H15B	0.9600
C8—O2	1.4961 (18)	C15—H15C	0.9600
C8—H8	0.9800	N1—H1	0.857 (18)
O1—C1—O2	121.90 (15)	C14—C9—N1	123.32 (15)
O1—C1—C2	129.47 (15)	C10—C9—N1	117.89 (14)
O2—C1—C2	108.63 (13)	O3—C10—C11	125.45 (16)
C7—C2—C3	121.92 (15)	O3—C10—C9	114.46 (13)
C7—C2—C1	108.59 (13)	C11—C10—C9	120.08 (17)
C3—C2—C1	129.48 (14)	C10—C11—C12	119.96 (18)
C4—C3—C2	117.45 (15)	C10—C11—H11	120.0
C4—C3—H3	121.3	C12—C11—H11	120.0
C2—C3—H3	121.3	C13—C12—C11	120.42 (16)
C3—C4—C5	120.84 (16)	C13—C12—H12	119.8
C3—C4—H4	119.6	C11—C12—H12	119.8
C5—C4—H4	119.6	C12—C13—C14	120.02 (19)
C6—C5—C4	121.57 (17)	C12—C13—H13	120.0
C6—C5—H5	119.2	C14—C13—H13	120.0
C4—C5—H5	119.2	C13—C14—C9	120.76 (17)
C7—C6—C5	117.57 (15)	C13—C14—H14	119.6
C7—C6—H6	121.2	C9—C14—H14	119.6
C5—C6—H6	121.2	O3—C15—H15A	109.5
C2—C7—C6	120.64 (14)	O3—C15—H15B	109.5
C2—C7—C8	109.39 (13)	H15A—C15—H15B	109.5
C6—C7—C8	129.95 (13)	O3—C15—H15C	109.5
N1—C8—O2	112.46 (12)	H15A—C15—H15C	109.5
N1—C8—C7	114.88 (13)	H15B—C15—H15C	109.5
O2—C8—C7	102.73 (11)	C8—N1—C9	122.18 (14)
N1—C8—H8	108.8	C8—N1—H1	117.4 (11)
O2—C8—H8	108.8	C9—N1—H1	118.0 (11)
C7—C8—H8	108.8	C1—O2—C8	110.62 (11)
C14—C9—C10	118.72 (14)	C10—O3—C15	117.88 (13)
O1—C1—C2—C7	−177.63 (17)	N1—C9—C10—O3	−5.0 (2)
O2—C1—C2—C7	1.95 (17)	C14—C9—C10—C11	−2.4 (2)
O1—C1—C2—C3	2.3 (3)	N1—C9—C10—C11	174.67 (15)
O2—C1—C2—C3	−178.12 (15)	O3—C10—C11—C12	−179.49 (16)
C7—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	0.9 (3)
C1—C2—C3—C4	179.98 (15)	C10—C11—C12—C13	0.6 (3)
C2—C3—C4—C5	0.2 (2)	C11—C12—C13—C14	−0.7 (3)
C3—C4—C5—C6	0.1 (3)	C12—C13—C14—C9	−0.8 (3)
C4—C5—C6—C7	−0.5 (2)	C10—C9—C14—C13	2.4 (2)
C3—C2—C7—C6	−0.3 (2)	N1—C9—C14—C13	−174.53 (15)
C1—C2—C7—C6	179.62 (13)	O2—C8—N1—C9	−76.44 (17)
C3—C2—C7—C8	178.46 (14)	C7—C8—N1—C9	166.52 (13)
C1—C2—C7—C8	−1.60 (16)	C14—C9—N1—C8	−0.9 (2)
C5—C6—C7—C2	0.6 (2)	C10—C9—N1—C8	−177.79 (14)
C5—C6—C7—C8	−177.92 (15)	O1—C1—O2—C8	178.13 (15)
C2—C7—C8—N1	123.16 (14)	C2—C1—O2—C8	−1.48 (16)
C6—C7—C8—N1	−58.2 (2)	N1—C8—O2—C1	−123.54 (14)
C2—C7—C8—O2	0.71 (15)	C7—C8—O2—C1	0.52 (15)
C6—C7—C8—O2	179.34 (15)	C11—C10—O3—C15	−10.4 (2)
C14—C9—C10—O3	177.98 (13)	C9—C10—O3—C15	169.25 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86 (2)	2.286 (18)	2.6193 (18)	103.3 (16)
N1—H1···O1^i	0.857 (18)	2.441 (18)	3.224 (2)	152.1 (15)
C15—H15B···O1^ii	0.96	2.54	3.387 (2)	147

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