3-[(3-Oxo-1,3-dihydro­isobenzofuran-1-yl)amino]benzoic acid

Li, W.; Yin, H.; Wen, L.; Li, K.; Fan, W.

doi:10.1107/S1600536809038926

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2579

doi:10.1107/S1600536809038926

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3-[(3-Oxo-1,3-dihydroisobenzofuran-1-yl)amino]benzoic acid

Wenkuan Li,^a Handong Yin,^a ^* Liyuan Wen,^a Kang Li ^a and Weidong Fan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 18 September 2009; accepted 25 September 2009; online 30 September 2009)

In the title compound, C₁₅H₁₁NO₄, the dihedral angle formed by the benzene ring and isobenzofuran ring system is 67.82 (5) Å. The crystal structure is stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen-bonding interactions.

Related literature

For general background to isobenzofuran derivatives, see: Landge et al. (2008 ); Paradkar et al. (1998 ); Joseph (1998 ). Odabaşoğlu & Büyükgüngör (2008 ).

Experimental

Crystal data

C₁₅H₁₁NO₄
M_r = 269.25
Monoclinic, P 2₁ /n
a = 10.9025 (15) Å
b = 8.1595 (12) Å
c = 14.2654 (18) Å
β = 103.463 (1)°
V = 1234.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.27 × 0.19 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.982
6011 measured reflections
2171 independent reflections
1206 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 0.90
2171 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4ⁱ	0.82	1.91	2.712 (2)	166
N1—H1⋯O2ⁱⁱ	0.86	2.16	2.956 (2)	154
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038926/bq2162sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038926/bq2162Isup2.hkl

checkCIF report

Comment top

Phthalides (isobenzofuran-1(3H)-ones) are well known for their interesting biological properties (Paradkar et al., 1998; Joseph, 1998). In addition, 3-substituted phthalides are vital heterocyclic motifs in many bioactive compounds such as isocoumarins, anthraquinones, anthracyclines, and several alkaloids (Landge et al., 2008). In view of this, various methods have been reported for their synthesis. Herein, the crystal structure of the title compound is presented.

The title compound, (I), (Fig. 1) is a chirality compound with a chiral center at C₉. The dihedral angle between the benzene ring and isobenzofuran ring system is 67.82 (5) Å indicating that the two ring systems are not coplanar. The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen-bonding interactions (Fig. 2, Table. 1).

Related literature top

For general background to isobenzofuran derivatives, see: Landge et al. (2008); Paradkar et al. (1998); Joseph (1998). Odabaşoğlu & Büyükgüngör (2008).

Experimental top

To a ethanol solution (30 ml) of 3-aminobenzoic acid (3.00 mmol) added 3.00 mmol 2-formylbenzoic acid. The mixture solution was stirred at 343 K for 2.5 h. Then, sodium ethoxide (6.6 mmol) was added to the reactor and stirring for 0.5 h. Bis(tributyltin)oxide (0.3 mmol) was then added to the reactor and the reaction mixture was stirred for 6 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of dichloromethane/methanol (1:1) yielding the title compound unexpectedly. Anal. Calcd (%) for C₁₅H₁₁N₁O₄ (Mr = 269.25): C, 66.91; H, 4.12; N, 5.20; O, 23.77. Found (%): C, 66.87; H, 4.13; N, 5.21; O, 23.79.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of (I) with hydrogen bonding as dashed lines.

3-[(3-Oxo-1,3-dihydroisobenzofuran-1-yl)amino]benzoic acid top

Crystal data top

C₁₅H₁₁NO₄	F(000) = 560
M_r = 269.25	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1143 reflections
a = 10.9025 (15) Å	θ = 2.7–21.4°
b = 8.1595 (12) Å	µ = 0.11 mm⁻¹
c = 14.2654 (18) Å	T = 298 K
β = 103.463 (1)°	Block, colorless
V = 1234.2 (3) Å³	0.27 × 0.19 × 0.17 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2171 independent reflections
Radiation source: fine-focus sealed tube	1206 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
T_min = 0.972, T_max = 0.982	k = −9→9
6011 measured reflections	l = −16→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0513P)²] where P = (F_o² + 2F_c²)/3
2171 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₅H₁₁NO₄	V = 1234.2 (3) Å³
M_r = 269.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9025 (15) Å	µ = 0.11 mm⁻¹
b = 8.1595 (12) Å	T = 298 K
c = 14.2654 (18) Å	0.27 × 0.19 × 0.17 mm
β = 103.463 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2171 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1206 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.982	R_int = 0.038
6011 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.90	Δρ_max = 0.23 e Å⁻³
2171 reflections	Δρ_min = −0.13 e Å⁻³
181 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.77236 (15)	0.2945 (2)	0.94157 (13)	0.0511 (5)
H1	0.7596	0.2454	0.8868	0.061*
O1	0.99795 (14)	0.5570 (2)	1.25378 (11)	0.0745 (6)
H1A	1.0238	0.6014	1.3062	0.112*
O2	1.19133 (13)	0.45300 (19)	1.28827 (10)	0.0592 (5)
O3	0.62455 (14)	0.2734 (2)	1.04292 (10)	0.0614 (5)
O4	0.44272 (16)	0.1671 (2)	1.06184 (12)	0.0788 (6)
C1	1.0886 (2)	0.4649 (3)	1.23355 (15)	0.0469 (6)
C2	1.05166 (19)	0.3785 (3)	1.14008 (14)	0.0407 (5)
C3	0.92786 (18)	0.3817 (3)	1.08532 (15)	0.0425 (5)
H3	0.8673	0.4427	1.1063	0.051*
C4	0.89469 (18)	0.2949 (3)	1.00014 (15)	0.0402 (6)
C5	0.9866 (2)	0.2051 (3)	0.96999 (16)	0.0494 (6)
H5	0.9656	0.1478	0.9121	0.059*
C6	1.1080 (2)	0.2000 (3)	1.02457 (17)	0.0522 (6)
H6	1.1682	0.1378	1.0039	0.063*
C7	1.1418 (2)	0.2860 (3)	1.10972 (17)	0.0491 (6)
H7	1.2243	0.2821	1.1465	0.059*
C8	0.5015 (2)	0.2389 (3)	1.01183 (17)	0.0555 (7)
C9	0.67070 (19)	0.3691 (3)	0.96714 (15)	0.0478 (6)
H9	0.6952	0.4794	0.9916	0.057*
C10	0.55418 (18)	0.3801 (3)	0.88699 (15)	0.0422 (6)
C11	0.45572 (18)	0.3033 (3)	0.91465 (15)	0.0436 (6)
C12	0.3365 (2)	0.2979 (3)	0.85393 (16)	0.0558 (7)
H12	0.2700	0.2468	0.8729	0.067*
C13	0.3193 (2)	0.3700 (3)	0.76518 (16)	0.0592 (7)
H13	0.2400	0.3681	0.7232	0.071*
C14	0.4181 (2)	0.4451 (3)	0.73746 (16)	0.0590 (7)
H14	0.4042	0.4926	0.6766	0.071*
C15	0.53674 (19)	0.4520 (3)	0.79711 (16)	0.0514 (6)
H15	0.6029	0.5032	0.7777	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0355 (11)	0.0706 (14)	0.0439 (11)	0.0046 (9)	0.0027 (8)	−0.0129 (10)
O1	0.0506 (10)	0.1082 (15)	0.0594 (11)	0.0126 (10)	0.0017 (8)	−0.0300 (10)
O2	0.0406 (9)	0.0749 (12)	0.0529 (10)	−0.0040 (8)	−0.0077 (7)	0.0057 (9)
O3	0.0450 (10)	0.0930 (13)	0.0429 (10)	0.0050 (9)	0.0033 (7)	0.0062 (9)
O4	0.0656 (12)	0.1171 (17)	0.0559 (11)	−0.0037 (10)	0.0183 (9)	0.0242 (11)
C1	0.0398 (13)	0.0544 (15)	0.0446 (14)	−0.0052 (12)	0.0062 (11)	0.0065 (12)
C2	0.0365 (12)	0.0426 (13)	0.0410 (13)	−0.0027 (10)	0.0050 (10)	0.0029 (11)
C3	0.0359 (12)	0.0450 (14)	0.0450 (13)	0.0024 (10)	0.0065 (10)	−0.0004 (11)
C4	0.0333 (12)	0.0438 (14)	0.0412 (13)	−0.0018 (10)	0.0043 (10)	0.0009 (11)
C5	0.0443 (14)	0.0548 (15)	0.0499 (15)	−0.0004 (12)	0.0125 (11)	−0.0056 (12)
C6	0.0403 (14)	0.0549 (16)	0.0630 (16)	0.0059 (11)	0.0155 (12)	−0.0003 (13)
C7	0.0329 (13)	0.0529 (15)	0.0589 (16)	0.0003 (11)	0.0057 (10)	0.0071 (13)
C8	0.0464 (15)	0.0747 (19)	0.0448 (15)	0.0040 (13)	0.0091 (12)	0.0034 (13)
C9	0.0400 (13)	0.0575 (15)	0.0439 (14)	0.0017 (11)	0.0058 (10)	−0.0028 (12)
C10	0.0331 (12)	0.0499 (14)	0.0421 (13)	0.0039 (10)	0.0054 (10)	−0.0064 (11)
C11	0.0365 (13)	0.0559 (15)	0.0378 (13)	0.0021 (11)	0.0075 (10)	−0.0010 (11)
C12	0.0373 (13)	0.0786 (19)	0.0522 (15)	−0.0055 (12)	0.0120 (11)	−0.0035 (13)
C13	0.0375 (14)	0.0906 (19)	0.0448 (15)	0.0049 (13)	0.0002 (11)	−0.0022 (14)
C14	0.0477 (15)	0.0826 (19)	0.0454 (14)	0.0101 (13)	0.0082 (12)	0.0117 (14)
C15	0.0402 (13)	0.0630 (16)	0.0509 (15)	0.0002 (11)	0.0108 (11)	0.0046 (13)

Geometric parameters (Å, º) top

N1—C9	1.386 (3)	C6—C7	1.377 (3)
N1—C4	1.399 (2)	C6—H6	0.9300
N1—H1	0.8600	C7—H7	0.9300
O1—C1	1.326 (2)	C8—C11	1.458 (3)
O1—H1A	0.8200	C9—C10	1.501 (3)
O2—C1	1.211 (2)	C9—H9	0.9800
O3—C8	1.341 (3)	C10—C11	1.378 (3)
O3—C9	1.512 (3)	C10—C15	1.382 (3)
O4—C8	1.215 (3)	C11—C12	1.384 (3)
C1—C2	1.479 (3)	C12—C13	1.369 (3)
C2—C7	1.386 (3)	C12—H12	0.9300
C2—C3	1.394 (3)	C13—C14	1.375 (3)
C3—C4	1.380 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.374 (3)
C4—C5	1.388 (3)	C14—H14	0.9300
C5—C6	1.371 (3)	C15—H15	0.9300
C5—H5	0.9300

C9—N1—C4	123.46 (18)	O4—C8—C11	128.4 (2)
C9—N1—H1	118.3	O3—C8—C11	109.5 (2)
C4—N1—H1	118.3	N1—C9—C10	114.38 (18)
C1—O1—H1A	109.5	N1—C9—O3	112.41 (18)
C8—O3—C9	110.22 (17)	C10—C9—O3	102.25 (17)
O2—C1—O1	122.0 (2)	N1—C9—H9	109.2
O2—C1—C2	124.1 (2)	C10—C9—H9	109.2
O1—C1—C2	113.96 (17)	O3—C9—H9	109.2
C7—C2—C3	120.0 (2)	C11—C10—C15	120.71 (18)
C7—C2—C1	118.49 (19)	C11—C10—C9	109.41 (19)
C3—C2—C1	121.4 (2)	C15—C10—C9	129.9 (2)
C4—C3—C2	120.3 (2)	C10—C11—C12	121.0 (2)
C4—C3—H3	119.8	C10—C11—C8	108.61 (18)
C2—C3—H3	119.8	C12—C11—C8	130.3 (2)
C3—C4—C5	118.93 (18)	C13—C12—C11	118.2 (2)
C3—C4—N1	123.01 (19)	C13—C12—H12	120.9
C5—C4—N1	118.05 (19)	C11—C12—H12	120.9
C6—C5—C4	120.8 (2)	C12—C13—C14	120.6 (2)
C6—C5—H5	119.6	C12—C13—H13	119.7
C4—C5—H5	119.6	C14—C13—H13	119.7
C5—C6—C7	120.7 (2)	C15—C14—C13	121.9 (2)
C5—C6—H6	119.7	C15—C14—H14	119.1
C7—C6—H6	119.7	C13—C14—H14	119.1
C6—C7—C2	119.3 (2)	C14—C15—C10	117.6 (2)
C6—C7—H7	120.3	C14—C15—H15	121.2
C2—C7—H7	120.3	C10—C15—H15	121.2
O4—C8—O3	122.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.82	1.91	2.712 (2)	166
N1—H1···O2ⁱⁱ	0.86	2.16	2.956 (2)	154

Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁NO₄
M_r	269.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.9025 (15), 8.1595 (12), 14.2654 (18)
β (°)	103.463 (1)
V (Å³)	1234.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.27 × 0.19 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	6011, 2171, 1206
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 0.90
No. of reflections	2171
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.13

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.82	1.91	2.712 (2)	166.0
N1—H1···O2ⁱⁱ	0.86	2.16	2.956 (2)	154.0

Symmetry codes: (i) −x+3/2, y+1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

We acknowledge the financial support of the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48). This work was also supported by the `Students Technology Cultural Innovation Fund' of Liaocheng University.

References

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