3-(4-Methyl­pyridin-2-ylamino)isobenzofuran-1(3H)-one

Crystals of the title compound, C₁₄H₁₂O₂N₂, are stabilized by inversion-related N—H...N and C—H...O inter­molecular hydrogen bonds and also by two C—H...π inter­actions. The N—H...N and C—H...O hydrogen bonds generate R₂²(8) and R₂²(10) ring motifs, respectively, and the phthalide section of the mol­ecule is planar. The dihedral angle between the phthalide group and the pyridyl ring is 82.06 (17)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.079
• wR factor = 0.237
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H6     ..  CG1     ..       3.37 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT481_ALERT_4_C Long D...A H-Bond Reported C6     ..  CG1     ..       4.04 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   2 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-methylpyridin-2-ylamino)isobenzofuran-1(3H)-one

Crystal data

C14H12N2O2	Z = 2
Mr = 240.26	F(000) = 252
Triclinic, P1	Dx = 1.273 Mg m^−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6621 (18) Å	Cell parameters from 5736 reflections
b = 8.0381 (18) Å	θ = 3.2–27.0°
c = 10.616 (2) Å	µ = 0.09 mm^−1
α = 87.387 (17)°	T = 296 K
β = 78.177 (18)°	Prism, colorless
γ = 78.456 (18)°	0.47 × 0.36 × 0.17 mm
V = 627.0 (2) Å^3

Data collection

Stoe IPDS-2 diffractometer	2454 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1575 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.079
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ω scan rotation method	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.960, Tmax = 0.987	l = −13→13
5736 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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.237	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0967P)^2 + 0.443P] where P = (Fo^2 + 2Fc^2)/3
2454 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.31 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	0.6909 (5)	0.5300 (5)	0.0678 (4)	0.0489 (9)
C2	0.6668 (5)	0.7127 (4)	0.0968 (3)	0.0451 (8)
C3	0.7730 (6)	0.8298 (5)	0.0444 (4)	0.0605 (10)
H3	0.8784	0.7984	−0.0176	0.073*
C4	0.7152 (7)	0.9957 (5)	0.0886 (5)	0.0688 (12)
H4	0.7825	1.0775	0.0548	0.083*
C5	0.5609 (7)	1.0411 (5)	0.1809 (5)	0.0679 (12)
H5	0.5263	1.1531	0.2087	0.081*
C6	0.4552 (6)	0.9249 (5)	0.2341 (4)	0.0591 (10)
H6	0.3510	0.9566	0.2971	0.071*
C7	0.5108 (5)	0.7583 (4)	0.1895 (4)	0.0488 (9)
C8	0.4177 (6)	0.6076 (4)	0.2213 (4)	0.0546 (9)
H8	0.3015	0.6307	0.1925	0.066*
C9	0.2854 (5)	0.4378 (5)	0.4009 (4)	0.0515 (9)
C13	0.2078 (7)	0.2619 (5)	0.5666 (4)	0.0646 (11)
H13	0.2263	0.2132	0.6451	0.077*
C12	0.0748 (6)	0.2148 (5)	0.5136 (4)	0.0563 (10)
H12	0.0061	0.1388	0.5567	0.068*
C11	0.0446 (6)	0.2820 (4)	0.3951 (4)	0.0525 (9)
C10	0.1567 (6)	0.3947 (5)	0.3365 (4)	0.0572 (10)
H10	0.1459	0.4405	0.2558	0.069*
C14	−0.0984 (8)	0.2351 (6)	0.3326 (5)	0.0767 (14)
H14A	−0.1319	0.3219	0.2719	0.115*
H14C	−0.2034	0.2248	0.3973	0.115*
H14B	−0.0509	0.1289	0.2886	0.115*
N1	0.3887 (5)	0.5609 (4)	0.3519 (3)	0.0600 (9)
H1	0.4358	0.6093	0.4036	0.072*
N2	0.3127 (5)	0.3727 (4)	0.5136 (3)	0.0582 (9)
O1	0.8086 (4)	0.4395 (4)	−0.0065 (3)	0.0637 (8)
O2	0.5472 (4)	0.4701 (3)	0.1407 (3)	0.0588 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.053 (2)	0.0472 (19)	0.051 (2)	−0.0101 (17)	−0.0200 (18)	−0.0023 (16)
C2	0.052 (2)	0.0384 (17)	0.0496 (19)	−0.0111 (15)	−0.0192 (17)	0.0027 (14)
C3	0.065 (3)	0.058 (2)	0.067 (2)	−0.027 (2)	−0.018 (2)	0.0084 (18)
C4	0.086 (3)	0.049 (2)	0.085 (3)	−0.035 (2)	−0.030 (3)	0.015 (2)
C5	0.085 (3)	0.0355 (18)	0.090 (3)	−0.015 (2)	−0.031 (3)	0.0004 (19)
C6	0.064 (2)	0.0385 (18)	0.074 (3)	−0.0057 (17)	−0.015 (2)	−0.0077 (17)
C7	0.058 (2)	0.0365 (17)	0.056 (2)	−0.0129 (16)	−0.0196 (18)	0.0026 (14)
C8	0.067 (2)	0.0412 (18)	0.057 (2)	−0.0110 (17)	−0.0142 (19)	−0.0031 (15)
C9	0.054 (2)	0.0476 (19)	0.055 (2)	−0.0170 (17)	−0.0073 (17)	−0.0106 (16)
C13	0.080 (3)	0.052 (2)	0.070 (3)	−0.026 (2)	−0.026 (2)	0.0125 (19)
C12	0.066 (2)	0.0451 (19)	0.064 (2)	−0.0242 (18)	−0.016 (2)	0.0074 (17)
C11	0.067 (2)	0.0383 (17)	0.056 (2)	−0.0153 (17)	−0.0158 (19)	−0.0030 (15)
C10	0.074 (3)	0.051 (2)	0.048 (2)	−0.0128 (19)	−0.0151 (19)	0.0038 (16)
C14	0.099 (4)	0.064 (3)	0.084 (3)	−0.032 (3)	−0.044 (3)	0.006 (2)
N1	0.081 (2)	0.0580 (18)	0.0524 (18)	−0.0325 (18)	−0.0232 (17)	0.0037 (14)
N2	0.069 (2)	0.0550 (18)	0.060 (2)	−0.0237 (16)	−0.0244 (17)	0.0085 (15)
O1	0.0621 (17)	0.0595 (16)	0.0711 (18)	−0.0037 (14)	−0.0214 (15)	−0.0151 (14)
O2	0.0783 (19)	0.0372 (13)	0.0634 (16)	−0.0190 (13)	−0.0120 (14)	−0.0013 (11)

Geometric parameters (Å, º)

C1—O1	1.209 (5)	C8—H8	0.9800
C1—O2	1.369 (5)	C9—N2	1.323 (5)
C1—C2	1.481 (5)	C9—N1	1.406 (5)
C2—C7	1.381 (5)	C9—C10	1.412 (5)
C2—C3	1.390 (5)	C13—N2	1.346 (5)
C3—C4	1.389 (6)	C13—C12	1.381 (6)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.370 (7)	C12—C11	1.390 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.384 (6)	C11—C10	1.409 (5)
C5—H5	0.9300	C11—C14	1.507 (6)
C6—C7	1.395 (5)	C10—H10	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—C8	1.517 (5)	C14—H14C	0.9600
C8—N1	1.403 (5)	C14—H14B	0.9600
C8—O2	1.496 (5)	N1—H1	0.8600
O1—C1—O2	121.5 (3)	N2—C9—N1	114.7 (3)
O1—C1—C2	130.5 (4)	N2—C9—C10	123.4 (3)
O2—C1—C2	107.9 (3)	N1—C9—C10	121.8 (3)
C7—C2—C3	121.6 (3)	N2—C13—C12	125.2 (4)
C7—C2—C1	108.7 (3)	N2—C13—H13	117.4
C3—C2—C1	129.6 (4)	C12—C13—H13	117.4
C4—C3—C2	117.2 (4)	C13—C12—C11	119.4 (4)
C4—C3—H3	121.4	C13—C12—H12	120.3
C2—C3—H3	121.4	C11—C12—H12	120.3
C5—C4—C3	121.2 (4)	C12—C11—C10	116.2 (3)
C5—C4—H4	119.4	C12—C11—C14	121.8 (4)
C3—C4—H4	119.4	C10—C11—C14	122.0 (4)
C4—C5—C6	121.8 (4)	C11—C10—C9	119.7 (3)
C4—C5—H5	119.1	C11—C10—H10	120.1
C6—C5—H5	119.1	C9—C10—H10	120.1
C5—C6—C7	117.4 (4)	C11—C14—H14A	109.5
C5—C6—H6	121.3	C11—C14—H14C	109.5
C7—C6—H6	121.3	H14A—C14—H14C	109.5
C2—C7—C6	120.6 (3)	C11—C14—H14B	109.5
C2—C7—C8	109.6 (3)	H14A—C14—H14B	109.5
C6—C7—C8	129.7 (4)	H14C—C14—H14B	109.5
N1—C8—O2	111.0 (3)	C8—N1—C9	122.2 (3)
N1—C8—C7	114.7 (3)	C8—N1—H1	118.9
O2—C8—C7	102.3 (3)	C9—N1—H1	118.9
N1—C8—H8	109.6	C9—N2—C13	116.1 (3)
O2—C8—H8	109.6	C1—O2—C8	111.3 (3)
C7—C8—H8	109.6
O1—C1—C2—C7	−179.9 (4)	N2—C13—C12—C11	1.2 (7)
O2—C1—C2—C7	1.6 (4)	C13—C12—C11—C10	0.6 (6)
O1—C1—C2—C3	0.9 (6)	C13—C12—C11—C14	179.9 (4)
O2—C1—C2—C3	−177.7 (4)	C12—C11—C10—C9	−2.3 (6)
C7—C2—C3—C4	−0.4 (6)	C14—C11—C10—C9	178.4 (4)
C1—C2—C3—C4	178.8 (4)	N2—C9—C10—C11	2.5 (6)
C2—C3—C4—C5	0.7 (6)	N1—C9—C10—C11	−174.2 (4)
C3—C4—C5—C6	−0.3 (7)	O2—C8—N1—C9	−72.5 (5)
C4—C5—C6—C7	−0.4 (7)	C7—C8—N1—C9	172.2 (4)
C3—C2—C7—C6	−0.3 (5)	N2—C9—N1—C8	161.4 (4)
C1—C2—C7—C6	−179.6 (3)	C10—C9—N1—C8	−21.6 (6)
C3—C2—C7—C8	176.3 (3)	N1—C9—N2—C13	176.2 (4)
C1—C2—C7—C8	−3.1 (4)	C10—C9—N2—C13	−0.8 (6)
C5—C6—C7—C2	0.7 (6)	C12—C13—N2—C9	−1.1 (6)
C5—C6—C7—C8	−175.1 (4)	O1—C1—O2—C8	−178.1 (3)
C2—C7—C8—N1	123.5 (4)	C2—C1—O2—C8	0.6 (4)
C6—C7—C8—N1	−60.4 (6)	N1—C8—O2—C1	−125.1 (3)
C2—C7—C8—O2	3.3 (4)	C7—C8—O2—C1	−2.3 (4)
C6—C7—C8—O2	179.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.86	2.31	3.075 (5)	149
C8—H8···O1^ii	0.98	2.43	3.211 (6)	136
C6—H6···Cg1^iii	0.93	3.37	4.039 (4)	131
C13—H13···Cg2^i	0.93	2.82	3.702 (5)	160

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