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

In the mol­ecule of the title compound, C₁₄H₁₀ClNO₂, the essentially planar phthalide group is oriented at a dihedral angle of 59.43 (4)° with respect to the substituted aromatic ring. In the crystal structure, inter­molecular C—H...O and N—H...O hydrogen bonds link the mol­ecules, generating R₄⁴(21) ring motifs to form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.068
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Alert level C
SHFSU01_ALERT_2_C  Test not performed. _refine_ls_shift/su_max and
            _refine_ls_shift/esd_max not present.
            Absolute value of the parameter shift to su ratio given   0.001

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           25.99
           From the CIF: _reflns_number_total               2433
           Count of symmetry unique reflns         1227
           Completeness (_total/calc)            198.29%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1206
           Fraction of Friedel pairs measured     0.983
           Are heavy atom types Z>Si present        yes
PLAT792_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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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S1. Comment

Phthalides (isobenzofuranones) are five-membered lactones found in plants and they are known to show diverse biological activities, such as fungicidal, bactericidal, herbicidal, analgesic, pesticidal, hypotensive and vasorelaxant activities (Aoki et al., 1973; Tsi & Tan, 1997; Roy & Sarkar, 2005). In addition, phthalide derivatives are useful in the treatment of circulatory and heart-related diseases (Bellasio, 1974). As part of our ongoing research on 3-substituted phthalides, the title compound, (I), has been synthesized and its crystal structure is reported here.

In the molecule of (I), (Fig. 1), rings A (C2-C7), B (C1/C2/C7/C8/O2) and C (C9-C14) are, of course, planar. The dihedral angles between them are A/B = 2.45 (4)°, A/C = 59.93 (4)° and B/C = 58.90 (4)°. So, rings A and B are also nearly coplanar. Ring C is oriented with respect to the coplanar ring system at a dihedral angle of 59.43 (4)°. The geometry of (I) does not show any significant difference from the average geometry found for 3-(4-chloroanilino)isobenzofuran-1(3H)-one (Büyükgüngör & Odabaşoğlu, 2006).

In the crystal structure, intermolecular C-H···O and N-H···O hydrogen bonds (Table 1) link the molecules, generating R₄⁴(21) (Fig. 2) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure.

Related literature

For general background, see: Aoki et al. (1973, 1974); Tsi & Tan (1997); Roy & Sarkar (2005); Bellasio (1974, 1975). For related structures, see: Büyükgüngör & Odabaşoğlu (2006); Odabaşoğlu & Büyükgüngör (2006). For ring motif details, see: Bernstein et al. (1995); Etter (1990).

S2. Experimental

The title compound was prepared according to the method described by Odabaşoğlu & Büyükgüngör (2006), using phthalaldehydic acid and 2-chloroaniline as starting materials (yield; 84%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol-DMF (1:1) solution at room temperature.

S3. Refinement

H atom (for NH) was located in difference synthesis and refined freely [N-H = 0.84 (3) Å and U_iso(H) = 0.061 (6) Ų]. The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.98 Å for aromatic and methine H, respectively, and constrained to ride on their parent atoms with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I), showing the formation of R4^4(21) ring motif. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x - 1/2, 1 - y, z - 1/2; (ii) x - 1, y, z; (iii) x, 1 - y, 1/2 + z]. H atoms not involved in hydrogen bondings have been omitted for clarity.

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

Crystal data

C14H10ClNO2	F(000) = 536
Mr = 259.68	Dx = 1.385 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 7423 reflections
a = 9.2485 (8) Å	θ = 1.8–28.0°
b = 22.7915 (13) Å	µ = 0.30 mm^−1
c = 7.1111 (6) Å	T = 296 K
β = 123.823 (6)°	Prism, colorless
V = 1245.25 (19) Å^3	0.51 × 0.34 × 0.11 mm
Z = 4

Data collection

Stoe IPDS II diffractometer	2433 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2200 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.038
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
w–scan rotation method	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −28→28
Tmin = 0.880, Tmax = 0.969	l = −8→8
7423 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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0412P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2433 reflections	Δρmax = 0.12 e Å^−3
168 parameters	Δρmin = −0.15 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1205 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

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 > 2sigma(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
Cl1	0.32584 (7)	0.29431 (2)	−0.03793 (8)	0.06502 (16)
O1	0.48884 (19)	0.56863 (6)	0.4723 (2)	0.0568 (4)
O2	0.43774 (16)	0.47290 (5)	0.4752 (2)	0.0462 (3)
N1	0.4488 (2)	0.37749 (6)	0.3398 (3)	0.0446 (3)
H1	0.462 (3)	0.3829 (10)	0.233 (5)	0.061 (6)*
C1	0.5400 (2)	0.51868 (7)	0.5030 (3)	0.0418 (4)
C2	0.7123 (2)	0.49617 (8)	0.5728 (3)	0.0401 (4)
C3	0.8602 (3)	0.52646 (9)	0.6291 (3)	0.0507 (4)
H3	0.8604	0.5672	0.6209	0.061*
C4	1.0076 (3)	0.49429 (11)	0.6977 (3)	0.0616 (5)
H4	1.1095	0.5134	0.7368	0.074*
C5	1.0055 (3)	0.43377 (11)	0.7092 (4)	0.0622 (6)
H5	1.1068	0.4129	0.7568	0.075*
C6	0.8566 (3)	0.40333 (9)	0.6516 (3)	0.0545 (5)
H6	0.8558	0.3626	0.6584	0.065*
C7	0.7097 (2)	0.43588 (7)	0.5838 (3)	0.0404 (4)
C8	0.5336 (2)	0.41624 (7)	0.5234 (3)	0.0400 (3)
H8	0.5456	0.3977	0.6558	0.048*
C9	0.2979 (2)	0.34797 (7)	0.2808 (3)	0.0385 (4)
C10	0.2263 (3)	0.30630 (8)	0.1070 (3)	0.0473 (4)
C11	0.0825 (3)	0.27393 (9)	0.0501 (3)	0.0610 (6)
H11	0.0388	0.2462	−0.0651	0.073*
C12	0.0027 (3)	0.28242 (11)	0.1632 (4)	0.0678 (6)
H12	−0.0959	0.2610	0.1235	0.081*
C13	0.0701 (3)	0.32296 (9)	0.3359 (4)	0.0588 (5)
H13	0.0174	0.3285	0.4141	0.071*
C14	0.2156 (2)	0.35546 (8)	0.3937 (3)	0.0488 (4)
H14	0.2592	0.3828	0.5101	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0858 (4)	0.0647 (3)	0.0552 (2)	−0.0121 (3)	0.0459 (3)	−0.0150 (2)
O1	0.0704 (10)	0.0411 (7)	0.0633 (8)	0.0097 (6)	0.0399 (8)	0.0004 (6)
O2	0.0393 (6)	0.0438 (7)	0.0576 (7)	0.0011 (5)	0.0282 (6)	−0.0031 (5)
N1	0.0508 (9)	0.0446 (8)	0.0439 (8)	−0.0085 (7)	0.0297 (7)	−0.0057 (6)
C1	0.0468 (10)	0.0416 (9)	0.0371 (8)	0.0008 (8)	0.0234 (7)	−0.0028 (7)
C2	0.0406 (9)	0.0446 (9)	0.0332 (8)	−0.0032 (7)	0.0192 (7)	−0.0032 (6)
C3	0.0494 (11)	0.0577 (11)	0.0431 (8)	−0.0141 (9)	0.0245 (8)	−0.0071 (8)
C4	0.0403 (11)	0.0914 (16)	0.0487 (11)	−0.0170 (10)	0.0221 (9)	−0.0092 (10)
C5	0.0379 (10)	0.0905 (17)	0.0527 (11)	0.0122 (10)	0.0218 (9)	0.0000 (10)
C6	0.0496 (11)	0.0555 (11)	0.0552 (10)	0.0111 (9)	0.0271 (9)	0.0032 (9)
C7	0.0379 (9)	0.0445 (9)	0.0363 (8)	0.0015 (7)	0.0192 (7)	−0.0013 (7)
C8	0.0408 (9)	0.0381 (8)	0.0404 (8)	0.0015 (7)	0.0220 (7)	0.0001 (7)
C9	0.0399 (9)	0.0313 (8)	0.0405 (8)	0.0008 (7)	0.0201 (7)	0.0033 (6)
C10	0.0552 (11)	0.0431 (9)	0.0378 (8)	−0.0032 (8)	0.0223 (8)	−0.0001 (7)
C11	0.0629 (14)	0.0537 (11)	0.0523 (11)	−0.0203 (10)	0.0233 (10)	−0.0118 (9)
C12	0.0591 (13)	0.0671 (14)	0.0748 (14)	−0.0228 (10)	0.0358 (12)	−0.0053 (10)
C13	0.0551 (12)	0.0593 (13)	0.0726 (13)	−0.0092 (10)	0.0422 (11)	−0.0001 (10)
C14	0.0535 (11)	0.0456 (10)	0.0522 (10)	−0.0025 (8)	0.0324 (9)	−0.0022 (7)

Geometric parameters (Å, º)

N1—H1	0.84 (3)	C8—N1	1.400 (2)
C1—O1	1.205 (2)	C8—O2	1.494 (2)
C1—O2	1.347 (2)	C8—H8	0.9800
C1—C2	1.472 (3)	C9—N1	1.387 (2)
C2—C7	1.377 (2)	C9—C14	1.391 (2)
C2—C3	1.378 (3)	C9—C10	1.399 (2)
C3—C4	1.376 (3)	C10—C11	1.370 (3)
C3—H3	0.9300	C10—Cl1	1.744 (2)
C4—C5	1.383 (4)	C11—C12	1.375 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.385 (3)	C12—C13	1.377 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.378 (3)	C13—C14	1.383 (3)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.503 (3)	C14—H14	0.9300
C1—O2—C8	110.92 (13)	N1—C8—O2	112.25 (14)
C8—N1—H1	117.4 (16)	N1—C8—C7	114.17 (15)
C9—N1—C8	122.34 (16)	O2—C8—C7	102.62 (13)
C9—N1—H1	115.2 (17)	N1—C8—H8	109.2
O1—C1—O2	122.15 (17)	O2—C8—H8	109.2
O1—C1—C2	129.22 (17)	C7—C8—H8	109.2
O2—C1—C2	108.63 (14)	N1—C9—C14	123.22 (15)
C7—C2—C3	121.94 (17)	N1—C9—C10	119.92 (15)
C7—C2—C1	108.50 (15)	C14—C9—C10	116.80 (16)
C3—C2—C1	129.53 (17)	C11—C10—C9	122.08 (18)
C4—C3—C2	117.61 (19)	C11—C10—Cl1	119.09 (14)
C4—C3—H3	121.2	C9—C10—Cl1	118.82 (14)
C2—C3—H3	121.2	C10—C11—C12	120.02 (19)
C3—C4—C5	120.61 (19)	C10—C11—H11	120.0
C3—C4—H4	119.7	C12—C11—H11	120.0
C5—C4—H4	119.7	C11—C12—C13	119.48 (19)
C4—C5—C6	121.76 (19)	C11—C12—H12	120.3
C4—C5—H5	119.1	C13—C12—H12	120.3
C6—C5—H5	119.1	C12—C13—C14	120.4 (2)
C7—C6—C5	117.26 (19)	C12—C13—H13	119.8
C7—C6—H6	121.4	C14—C13—H13	119.8
C5—C6—H6	121.4	C13—C14—C9	121.18 (17)
C2—C7—C6	120.82 (17)	C13—C14—H14	119.4
C2—C7—C8	109.32 (14)	C9—C14—H14	119.4
C6—C7—C8	129.80 (16)
O1—C1—O2—C8	179.77 (16)	C2—C7—C8—O2	0.52 (17)
C2—C1—O2—C8	−0.24 (16)	C6—C7—C8—O2	177.69 (17)
O1—C1—C2—C7	−179.43 (17)	N1—C8—O2—C1	−123.18 (15)
O2—C1—C2—C7	0.59 (17)	C7—C8—O2—C1	−0.16 (16)
O1—C1—C2—C3	2.8 (3)	O2—C8—N1—C9	−73.5 (2)
O2—C1—C2—C3	−177.14 (15)	C7—C8—N1—C9	170.20 (15)
C7—C2—C3—C4	0.0 (3)	C14—C9—N1—C8	1.9 (3)
C1—C2—C3—C4	177.43 (17)	C10—C9—N1—C8	−174.97 (15)
C2—C3—C4—C5	0.0 (3)	N1—C9—C10—C11	176.68 (18)
C3—C4—C5—C6	0.3 (3)	C14—C9—C10—C11	−0.3 (2)
C4—C5—C6—C7	−0.5 (3)	N1—C9—C10—Cl1	−2.1 (2)
C3—C2—C7—C6	−0.2 (3)	C14—C9—C10—Cl1	−179.13 (13)
C1—C2—C7—C6	−178.15 (15)	C9—C10—C11—C12	0.8 (3)
C3—C2—C7—C8	177.25 (14)	Cl1—C10—C11—C12	179.56 (18)
C1—C2—C7—C8	−0.68 (18)	C10—C11—C12—C13	−1.0 (4)
C5—C6—C7—C2	0.5 (3)	C11—C12—C13—C14	0.8 (4)
C5—C6—C7—C8	−176.40 (17)	C12—C13—C14—C9	−0.3 (3)
C2—C7—C8—N1	122.25 (16)	N1—C9—C14—C13	−176.81 (18)
C6—C7—C8—N1	−60.6 (2)	C10—C9—C14—C13	0.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.84 (3)	2.29 (3)	3.091 (2)	159 (2)
C4—H4···O2^ii	0.93	2.54	3.397 (2)	153

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