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

The structure of the title compound, C₁₄H₁₀ClNO₂, is stabilized by N—H...O, C—H...π and π–π inter­actions. The phthalide part of the mol­ecule is planar and the dihedral angle between the phthalide group and the benzene ring is 75.58 (15)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.139
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H6     ..  CG1     ..       3.29 Ang.

Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 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, 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-(4-chloroanilino)isobenzofuran-1(3H)-one

Crystal data

C14H10ClNO2	F(000) = 536
Mr = 259.68	Dx = 1.395 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16688 reflections
a = 12.9256 (14) Å	θ = 1.9–27.9°
b = 7.2383 (10) Å	µ = 0.30 mm^−1
c = 15.6115 (16) Å	T = 296 K
β = 122.196 (7)°	Prismatic plate, pale yellow
V = 1236.0 (3) Å^3	0.60 × 0.42 × 0.16 mm
Z = 4

Data collection

Stoe IPDS 2 diffractometer	2422 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1385 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.090
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
φ–scan rotation method	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→8
Tmin = 0.848, Tmax = 0.955	l = −18→19
16688 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0645P)^2 + 0.036P] where P = (Fo^2 + 2Fc^2)/3
2422 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.22 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	−0.0602 (3)	0.6539 (4)	0.1814 (2)	0.0696 (7)
C2	−0.0331 (3)	0.6997 (3)	0.10313 (19)	0.0661 (7)
C3	−0.1129 (3)	0.7428 (4)	0.0023 (2)	0.0800 (8)
H3	−0.1968	0.7490	−0.0256	0.096*
C4	−0.0624 (4)	0.7762 (4)	−0.0555 (2)	0.0857 (9)
H4	−0.1133	0.8033	−0.1240	0.103*
C5	0.0629 (4)	0.7697 (4)	−0.0123 (2)	0.0888 (9)
H5	0.0945	0.7941	−0.0525	0.107*
C6	0.1419 (3)	0.7282 (4)	0.0882 (2)	0.0802 (8)
H6	0.2260	0.7257	0.1167	0.096*
C7	0.0913 (3)	0.6900 (4)	0.1459 (2)	0.0685 (7)
C8	0.1515 (3)	0.6305 (4)	0.2536 (2)	0.0708 (7)
H8	0.1902	0.5098	0.2621	0.085*
C9	0.3168 (2)	0.7160 (4)	0.4265 (2)	0.0678 (7)
C10	0.3829 (3)	0.8603 (5)	0.4909 (2)	0.0831 (9)
H10	0.3694	0.9802	0.4657	0.100*
C11	0.4683 (3)	0.8290 (5)	0.5917 (2)	0.0880 (9)
H11	0.5129	0.9267	0.6342	0.106*
C12	0.4871 (3)	0.6528 (5)	0.6289 (2)	0.0832 (9)
C13	0.4212 (3)	0.5084 (5)	0.5677 (2)	0.0874 (9)
H13	0.4341	0.3894	0.5940	0.105*
C14	0.3352 (3)	0.5395 (5)	0.4661 (2)	0.0805 (8)
H14	0.2897	0.4415	0.4245	0.097*
N1	0.2387 (2)	0.7557 (4)	0.32346 (18)	0.0752 (7)
O1	−0.15716 (19)	0.6504 (3)	0.17627 (15)	0.0834 (6)
O2	0.04538 (17)	0.6100 (3)	0.26746 (13)	0.0756 (5)
Cl1	0.59850 (9)	0.61279 (18)	0.75589 (6)	0.1182 (4)
H1	0.220 (2)	0.864 (4)	0.3083 (19)	0.059 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0787 (19)	0.0599 (16)	0.0654 (16)	−0.0044 (14)	0.0352 (15)	−0.0032 (12)
C2	0.0792 (19)	0.0572 (16)	0.0577 (15)	−0.0022 (13)	0.0337 (14)	−0.0042 (12)
C3	0.088 (2)	0.0740 (19)	0.0646 (17)	−0.0004 (16)	0.0317 (16)	−0.0065 (14)
C4	0.118 (3)	0.077 (2)	0.0589 (17)	0.0040 (18)	0.0449 (18)	−0.0027 (14)
C5	0.124 (3)	0.080 (2)	0.078 (2)	0.004 (2)	0.064 (2)	0.0008 (16)
C6	0.090 (2)	0.080 (2)	0.080 (2)	0.0082 (16)	0.0523 (17)	0.0023 (15)
C7	0.0827 (19)	0.0607 (16)	0.0670 (16)	0.0023 (14)	0.0432 (15)	−0.0027 (13)
C8	0.0752 (17)	0.0728 (18)	0.0660 (16)	0.0037 (15)	0.0386 (14)	0.0030 (14)
C9	0.0631 (16)	0.0783 (19)	0.0626 (16)	−0.0025 (14)	0.0339 (13)	0.0000 (14)
C10	0.082 (2)	0.082 (2)	0.0757 (19)	−0.0026 (16)	0.0354 (16)	0.0016 (16)
C11	0.082 (2)	0.099 (2)	0.074 (2)	−0.0102 (17)	0.0359 (17)	−0.0114 (18)
C12	0.0688 (18)	0.111 (3)	0.0668 (17)	0.0052 (18)	0.0342 (15)	0.0053 (17)
C13	0.080 (2)	0.096 (2)	0.084 (2)	0.0082 (18)	0.0421 (17)	0.0204 (18)
C14	0.0782 (19)	0.082 (2)	0.0729 (18)	−0.0036 (16)	0.0344 (15)	0.0064 (15)
N1	0.0787 (16)	0.0680 (17)	0.0694 (15)	0.0004 (14)	0.0331 (13)	0.0035 (13)
O1	0.0792 (14)	0.0857 (14)	0.0887 (14)	−0.0069 (11)	0.0471 (11)	0.0005 (10)
O2	0.0781 (12)	0.0872 (13)	0.0618 (11)	0.0012 (10)	0.0376 (10)	0.0073 (9)
Cl1	0.0970 (7)	0.1644 (10)	0.0694 (5)	0.0160 (6)	0.0284 (4)	0.0124 (5)

Geometric parameters (Å, º)

C1—O1	1.213 (3)	C8—O2	1.505 (3)
C1—O2	1.347 (3)	C8—H8	0.9800
C1—C2	1.477 (4)	C9—C14	1.384 (4)
C2—C7	1.375 (4)	C9—C10	1.384 (4)
C2—C3	1.382 (4)	C9—N1	1.400 (4)
C3—C4	1.388 (4)	C10—C11	1.377 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.384 (4)	C11—C12	1.368 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.374 (4)	C12—C13	1.366 (5)
C5—H5	0.9300	C12—Cl1	1.745 (3)
C6—C7	1.393 (4)	C13—C14	1.386 (4)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.492 (4)	C14—H14	0.9300
C8—N1	1.404 (4)	N1—H1	0.82 (2)
O1—C1—O2	121.5 (3)	C7—C8—H8	109.3
O1—C1—C2	130.0 (3)	O2—C8—H8	109.3
O2—C1—C2	108.5 (3)	C14—C9—C10	118.6 (3)
C7—C2—C3	122.3 (3)	C14—C9—N1	123.4 (3)
C7—C2—C1	108.6 (2)	C10—C9—N1	117.9 (3)
C3—C2—C1	129.1 (3)	C11—C10—C9	121.0 (3)
C2—C3—C4	117.1 (3)	C11—C10—H10	119.5
C2—C3—H3	121.5	C9—C10—H10	119.5
C4—C3—H3	121.5	C12—C11—C10	119.5 (3)
C5—C4—C3	120.7 (3)	C12—C11—H11	120.3
C5—C4—H4	119.7	C10—C11—H11	120.3
C3—C4—H4	119.7	C13—C12—C11	120.9 (3)
C6—C5—C4	121.9 (3)	C13—C12—Cl1	119.8 (3)
C6—C5—H5	119.0	C11—C12—Cl1	119.3 (3)
C4—C5—H5	119.0	C12—C13—C14	119.8 (3)
C5—C6—C7	117.5 (3)	C12—C13—H13	120.1
C5—C6—H6	121.3	C14—C13—H13	120.1
C7—C6—H6	121.3	C9—C14—C13	120.2 (3)
C2—C7—C6	120.4 (3)	C9—C14—H14	119.9
C2—C7—C8	109.5 (2)	C13—C14—H14	119.9
C6—C7—C8	130.0 (3)	C9—N1—C8	123.3 (3)
N1—C8—C7	114.2 (2)	C9—N1—H1	116.8 (18)
N1—C8—O2	111.6 (2)	C8—N1—H1	113.9 (18)
C7—C8—O2	102.8 (2)	C1—O2—C8	110.5 (2)
N1—C8—H8	109.3
O1—C1—C2—C7	178.1 (3)	C14—C9—C10—C11	2.2 (4)
O2—C1—C2—C7	−2.6 (3)	N1—C9—C10—C11	−175.0 (3)
O1—C1—C2—C3	−3.2 (5)	C9—C10—C11—C12	−0.8 (5)
O2—C1—C2—C3	176.1 (3)	C10—C11—C12—C13	−0.8 (5)
C7—C2—C3—C4	0.1 (4)	C10—C11—C12—Cl1	178.1 (2)
C1—C2—C3—C4	−178.5 (3)	C11—C12—C13—C14	0.8 (5)
C2—C3—C4—C5	−1.2 (4)	Cl1—C12—C13—C14	−178.1 (2)
C3—C4—C5—C6	0.8 (5)	C10—C9—C14—C13	−2.1 (4)
C4—C5—C6—C7	0.8 (5)	N1—C9—C14—C13	174.9 (3)
C3—C2—C7—C6	1.5 (4)	C12—C13—C14—C9	0.7 (5)
C1—C2—C7—C6	−179.7 (2)	C14—C9—N1—C8	14.5 (4)
C3—C2—C7—C8	−176.8 (2)	C10—C9—N1—C8	−168.4 (3)
C1—C2—C7—C8	2.0 (3)	C7—C8—N1—C9	−171.3 (3)
C5—C6—C7—C2	−1.9 (4)	O2—C8—N1—C9	72.6 (3)
C5—C6—C7—C8	176.0 (3)	O1—C1—O2—C8	−178.5 (2)
C2—C7—C8—N1	−121.8 (3)	C2—C1—O2—C8	2.1 (3)
C6—C7—C8—N1	60.0 (4)	N1—C8—O2—C1	121.9 (2)
C2—C7—C8—O2	−0.8 (3)	C7—C8—O2—C1	−0.9 (3)
C6—C7—C8—O2	−178.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.82 (2)	2.29 (3)	3.046 (4)	155 (2)
C6—H6···Cg1^ii	0.93	3.29	3.987 (4)	134

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.