Crystal and Molecular Structure of N-[2-(6-Methoxy-2-oxo-2H-Chromen-4-yl-Benzofuran-3-yl]- Benzamide

doi:10.4236/csta.2012.13020

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Crystal Structure Theory and Applications, 2012, 1, 107-113

http://dx.doi.org/10.4236/csta.2012.13020 Published Online December 2012 (http://www.SciRP.org/journal/csta)

Crystal and Molecular Structure of

N-[2-(6-Methoxy-2-oxo-2H-Chromen-4-yl-Benzofuran-3-yl]-

Benzamide

G. Anuradha1, G. Vasuki1*, Imtiyaz Ahmed Khan2, Manohar V. Kulkarni2

1Department of Physics, Kunthavai Naachiar Government Arts College, Thanjavur, India

2Department of Chemistry, Karnatak University, Dharwad, India

Email: *[email protected]

Received October 28, 2012; revised November 25, 2012; accepted December 3, 2012

ABSTRACT

The crystal structure of the potential active N-[2-(6-Methoxy-2-oxo-2H-chromen-4-yl)-benzofuran-3-yl]-benzamide

(C25H17NO5) (I) has been determined from single crystal X-ray diffraction data. The title compound crystallizes in the

monoclinic space group P 21/n, with a = 12.0551(11), b = 9.7853(8), c = 16.6517(16) Å, β = 90.092(4)˚, V = 1964.28(3)

Å3, Dcalc = 1.391 Mg/m3, Z = 4. In the structure, intermolecular H-bonds lead to the formation of a centrosymmetric

dimer of the molecule. There is an intramolecular C7—H7…N1 hydrogen bond forming a closed seven membered ring.

There are also intramolecular π-π interactions presented between the 3,6-Dihydro-2H-pyran ring of the chromen moiety

[Cg2…Cg2 distance = 3.5812(13) Å]. The packing structure is stabilized by these C—H…N, N—H…O hydrogen

bonds, C—H… π and π…π interactions.

Keywords: Benzamide; Benzofuran; 2H-Chromen; Single Crystal Structure; X-Ray Diffraction

1. Introduction

The amide and sulfonamide moieties are the constituents

of many biologically important compounds [1]. Cou-

marin derivatives are known to be an interesting class of

natural or synthetic compounds, whose biological activ-

ity varies according to the substitutes on the benzopyran

ring. Their antibacterial, antifungal, antitumor, anti-HIV

and anti-inflammatory and analgesic activities have been

published [2]. Benzamide derivatives, known for their

anti-inflammatory and immunomodulatory, anti-tumoral,

antipsychotic and antiallergic activities, are drugs widely

used in medicine [3]. Benzanilides and benzamides ex-

hibit wide range of biological activity and are extensively

used in organic synthesis. Various N-substituted benza-

mides exhibit potent antiemetic activity [4]. The benzani-

lide core is presented in compounds with such a wide

range of biological activities that it has been called a

privileged structure. Benzanilides have established their

efficacy as centroid elements of ligands that bind to a

wide variety of receptor types. Thus benzanilides con-

taining aminoalkyl groups originally designed as a pep-

tidomimetic, have been incorporated in an Arg-Gly-Asp

cyclic peptide yielding a high affinity GΠIb/IIIa ligand.

Imatinib is an ATP-site binding kinase inhibitor and

platelet-derived growth factor receptor kinases. Pyridyl-

methyl containing benzanilide are vascular endothelial

growth factor receptor and tyrosine kinase inhibitor. Fur-

thermore, benzamides have been reported to have acti-

vities as acetyl-CoA carboxylase and farnesyl transferase

inhibitors [5]. N-substituted benzamides are well known

anticancer compounds and the mechanism of action for

N-substituted benzamide-induced apoptosis has been

studied, using declopramide as a lead compound. N-sub-

stituted benzamides inhibit the activity of nuclear factor-

B and nuclear factor of activated T cells activity while

inducing activator protein 1 activity in T lymphocytes.

Various N-substituted benzamides exhibit potent antie-

metic activity, while heterocyclic analogs of benzanilide

derivatives are potassium channel activators. O-Aryloxy-

lation of N-substituted benzamides induced by the copper

(II)/trimethylamine N-oxide system has been studied.

N-Alkylated 2-nitrobenzamides are intermediates in the

synthesis of dibenzo[b,e] [1,4] diazepines and N-Acyl-

2-nitrobenzamides are precursors of 2,3-disubstitued 3H-

quinazoline-4-ones. A one-pot conversion of 2-nitro-n-

arylbenzamides to 2,3-dihydro-1H-quinazoline-4-ones has

also been reported [6]. As a part of studying the ring and

side-chain substitutions on the crystal structures of che-

mically and biologically important class of compounds

such as benzanilides, we report herein the crystal struc-

*Corresponding author.

G. ANURADHA ET AL.

108

ture of the title compound (I).

2. Experimental

2.1. Synthesis of the Title Compound

A suspension of 0.01 mole of 4-(3’-amino-2’-benzo (b)

furanyl) coumarin and 8ml of benzoyl chloride was hea-

ted and stirred at 80˚C for about 45 minutes. The mixture

was cooled and solid separated was washed thoroughly

with cold water and then with ethyl acetate to give suffi-

ciently pure product. The compound is crystallised in

alcohol, yield 93%, melting point 204˚C. The compound

is recrystallized from ethanol to get good quality single

crystals.

2.2. X-Ray Crystallography

For the crystal structure determination, the single crystal

of the compound C25H17NO5 was used for data collection

on a Bruker Kappa APEXII CCD diffractometer [7]. The

MoKα radiation of wavelength, (λ = 0.71073 Å) and

multi-scan technique for absorption correction were used

for data collection. The lattice parameters were deter-

mined by the least-squares methods on the basis of all

reflections with F2 > 2σ (F2). The structures were solved

by direct methods using SHELXS-97 and refined by a

full-matrix least-squares procedure using the program

SHELXL-97 [8,9]. H atoms were positioned geometri-

cally and refined using a riding model, fixing the aro-

matic C—H distances at 0.93 Å [Uiso(H) = 1.2 Ueq (C)].

The softwares used for Molecular graphics are ORTEP-3

for Windows [10] and PLATON [11]. The software used

to prepare material for publication is WinGX publication

routines [12]. Chemical structure of the title compound is

shown in Figure 1. Molecular structure of the compound

showing the atomic numbering scheme is shown in Fig-

ure 2(a). The crystallography details for the structures

determination of the compound are presented in Table 1.

Atomic coordinates and equivalent isotropic displace-

ment parameters are shown in Table 2. Bond lengths and

bond angles are shown in Table 3. Anisotropic dis-

placement parameters are shown in Table 4. Hydrogen

coordinates and isotropic displacement parameters are

shown in Table 5. Torsion angles and Hydrogen bond

geometry are shown in Tables 6 and 7 respectively.

Figure 1. Chemical structure of the title compound.

3. Results and Discussion

Title compound crystallizes in the monoclinic centro-

symmetric space group P21/n (No: 14) with Z = 4. The

structure of the compound consists of 6-Methoxy-2-oxo-

2H-chromen and Benzofuran fragments that connect to

the benzamide moiety. None of the aromatic systems are

coplanar with the benzamide unit. Dihedral angles be-

tween 1 - 2, 1 - 3 planes have been calculated. The mean

plane through the benzamide unit (1 = N1/C19/O5/C20-

C25) is inclined at a dihedral angle of 65.85(5)˚ with

respect to the benzofuran unit (2 = O4/C11-C18) and

79.36(5)˚ with respect to the 2H-chromen (3 = C2-C10/

O2) ring system. The C11—C12—N1 angle is 126.86

(19)˚, implying that the benzofuran ring system attached

at the N1 atom is pushed away from the benzamide unit.

The relative orientation of this benzofuran system with

(a)

(b)

Figure 2. (a): Molecular structure of the title compound

showing the atomic numbering system; (b): Molecular struc-

ture with different orientation of benzoyl group and benzo-

furan ring. Displacement ellipsoids are drawn at the 50%

probability level.

G. ANURADHA ET AL. 109

respect to the 2H-chromen moiety is determined by the

C8—C11—C12—N1 torsion angle 5.4(4)˚, correspond-

ing to + sp.

The title compound shows an intramolecular C—

H…N hydrogen bond (Table 7) which results in the for-

mation of a seven membered ring (N1—C12—C11—

C8—C6—C7—H7) and leads to a synperiplanar confor-

mation between the benzofuran group and the 2H-chro-

men group. The torsion angles in this region, N1— C12—

C11—C8, 5.4(4)˚ and C7—C6—C8—C11, –1.5 (3)˚

confirm this conformation. This formation forces the two

amide hydrogen atoms to the opposite direction.

In the crystal structure, two intermolecular N—H…O

[N(1)…O(3)a = 3.003(3) Å, N(1)—H(1)…O(3)a =

156(2)˚, symmetry code (a); 2-x,-y,-z] H-bonds, which

lead to the formation of a centrosymmetric dimer of the

molecule in the crystal unit cell (Figure 3). Here the

molecules are linked by paired N1—H1…O3 hydrogen

bonds in R22(16) dimers, which are further linked into chains

Table 1. Crystal data and structure refinement.

Temperature 293(2) K

Wavelength 0.71073 Å

Crystal system monoclinic

Space group P 21/n

Unit cell dimensions a = 12.0551(11) Å α = 90˚

b = 9.7853(8) Å β = 90.092

(4)˚

c = 16.6517(16) Å γ = 90˚

Volume 1964.3(3) Å3

Z 4

Density (calculated) 1.391 Mg/m3

Absorption coefficient 0.098 mm−1

F(000) 856

Crystal size 0.20 × 0.20 × 0.20 mm3

Theta range for

data collection 1.22˚ to 24.99˚

Index ranges –14 < = h < = 14, –11< =

k < = 8, –19 < = l < = 19

Reflections collected 17190

Independent reflections 3455 [R(int) = 0.0428]

Completeness to theta =

24.99˚ 99.90%

Max. and min. transmission 0.9807 and 0.9807

Refinement method Full-matrix least-squares on

Data/restraints/parameters 3455/0/287

Goodness-of-fit on F2 1.038

Final R indices [I >

2sigma(I)] R1 = 0.0370, wR2 = 0.0845

R indices (all data) R1 = 0.0476, wR2 = 0.0915

Extinction coefficient 0.0073(9)

Largest diff. peak and hole 0.212 and –0.152 e·Å−3

Table 2. Atomic coordinates (× 104) and equivalent isotropic

displacement parameters (Å2 × 103). U(eq) is defined as one

third of the trace of the orthogonalized Uij tensor.

x y z U(eq)

O(4) 11144(1)2298(2) 2014(1) 40(1)

O(3) 12148(2)–307(2) –446(1) 60(1)

O(1) 7940(2) 5367(2) –523(1) 53(1)

N(1) 8170(2) 2391(2) 1750(1) 34(1)

C(11) 10195(2)2252(2) 1543(1) 34(1)

C(6) 9883(2) 2613(2) 43(1) 35(1)

C(9) 11192(2)948(2) 541(1) 40(1)

O(2) 11010(1)1284(2) –869(1) 51(1)

C(12) 9283(2) 2508(2) 1994(1) 31(1)

C(22) 4702(2) 1585(2) 1476(1) 44(1)

C(8) 10416(2)1898(2) 704(1) 33(1)

C(21) 5822(2) 1785(2) 1598(1) 38(1)

C(17) 9826(3) 3160(2) 4199(1) 56(1)

C(23) 3985(2) 2668(3) 1497(2) 48(1)

C(13) 9665(2) 2758(2) 2800(1) 34(1)

C(14) 10800(2)2625(2) 2776(1) 39(1)

C(16) 10973(3)3039(3) 4152(2) 59(1)

C(7) 9102(2) 3667(2) 126(1) 35(1)

C(24) 4385(2) 3955(3) 1640(2) 60(1)

O(5) 7707(1) 4463(2) 2222(1) 55(1)

C(20) 6234(2) 3079(2) 1749(1) 32(1)

C(15) 11489(2)2776(3) 3437(2) 53(1)

C(2) 8700(2) 4331(2) –541(1) 39(1)

C(5) 10230(2)2292(2) –725(1) 42(1)

C(18) 9156(2) 3031(2) 3532(1) 44(1)

C(10) 11496(2)581(3) –263(2) 44(1)

C(4) 9847(2) 2982(3) –1391(1) 55(1)

C(3) 9084(2) 4005(3) –1305(1) 51(1)

C(25) 5493(2) 4158(2) 1772(2) 51(1)

C(19) 7416(2) 3373(2) 1930(1) 34(1)

C(1) 7353(2) 5572(3) 195(2) 68(1)

by means of C—H…π (Table 7) and π…π stacking in-

teractions. The latter involve the intramolecular interac-

tions between 3,6-Dihydro-2H-pyran rings (O2,C5,C6,

C8,C9,C10 = Cg2) of the chromen moiety [Cg2…Cg2

distance = 3.5812(13) Å; symmetry code: (i) 2-x,-y,-z].

Packing diagram and H bonding geometry along the

a-axis [symmetry code: 2-x,-y,-z] is shown in Figure 4.

H atoms involved in the interactions have only been

shown in this Figure.

IR spectral details:

IR data of the title compound are:

3302 (-NH-), 1696 (C = O), 1678 (C = O), 1616 (-C = C),

1036 (-C-O-C-).

G. ANURADHA ET AL.

110

Table 3. Bond lengths [Å] and angles [˚].

O(4)-C(14) 1.375(3) C(12)-C(11)-C(8) 136.1(2)

O(4)-C(11) 1.386(3) O(4)-C(11)-C(8) 113.33(18)

O(3)-C(10) 1.211(3) C(5)-C(6)-C(7) 117.6(2)

O(1)-C(2) 1.367(3) C(5)-C(6)-C(8) 117.2(2)

O(1)-C(1) 1.404(3) C(7)-C(6)-C(8) 125.05(19)

N(1)-C(19) 1.357(3) C(8)-C(9)-C(10) 122.6(2)

N(1)-C(12) 1.406(3) C(8)-C(9)-H(9) 118.7

N(1)-H(1) 0.87(3) C(10)-C(9)-H(9) 118.7

C(11)-C(12) 1.355(3) C(10)-O(2)-C(5) 121.76(18)

C(11)-C(8) 1.465(3) C(11)-C(12)-N(1) 126.86(19)

C(6)-C(5) 1.381(3) C(11)-C(12)-C(13) 106.78(19)

C(6)-C(7) 1.404(3) N(1)-C(12)-C(13) 125.96(19)

C(6)-C(8) 1.453(3) C(23)-C(22)-C(21) 120.3(2)

C(9)-C(8) 1.347(3) C(23)-C(22)-H(22) 119.8

C(9)-C(10) 1.434(3) C(21)-C(22)-H(22) 119.8

C(9)-H(9) 0.93 C(9)-C(8)-C(6) 119.1(2)

O(2)-C(10) 1.353(3) C(9)-C(8)-C(11) 118.84(19)

O(2)-C(5) 1.384(3) C(6)-C(8)-C(11) 121.91(19)

C(12)-C(13) 1.439(3) C(22)-C(21)-C(20) 120.5(2)

C(22)-C(23) 1.368(3) C(22)-C(21)-H(21) 119.8

C(22)-C(21) 1.380(3) C(20)-C(21)-H(21) 119.8

C(22)-H(22) 0.93 C(18)-C(17)-C(16) 121.9(2)

C(21)-C(20) 1.384(3) C(18)-C(17)-H(17) 119.1

C(21)-H(21) 0.93 C(16)-C(17)-H(17) 119.1

C(17)-C(18) 1.378(4) C(22)-C(23)-C(24) 119.6(2)

C(17)-C(16) 1.389(4) C(22)-C(23)-H(23) 120.2

C(17)-H(17) 0.93 C(24)-C(23)-H(23) 120.2

C(23)-C(24) 1.370(4) C(14)-C(13)-C(18) 118.9(2)

C(23)-H(23) 0.93 C(14)-C(13)-C(12) 105.94(19)

C(13)-C(14) 1.374(3) C(18)-C(13)-C(12) 135.1(2)

C(13)-C(18) 1.393(3) C(13)-C(14)-O(4) 110.51(19)

C(14)-C(15) 1.385(3) C(13)-C(14)-C(15) 124.3(2)

C(16)-C(15) 1.368(4) O(4)-C(14)-C(15) 125.2(2)

C(16)-H(16) 0.93 C(15)-C(16)-C(17) 121.3(2)

C(7)-C(2) 1.375(3)

C(15)-C(16)-H(16) 119.3

C(7)-H(7) 0.93 C(17)-C(16)-H(16) 119.3

C(24)-C(25) 1.368(3) C(2)-C(7)-C(6) 120.2(2)

C(24)-H(24) 0.93 C(2)-C(7)-H(7) 119.9

O(5)-C(19) 1.223(2) C(6)-C(7)-H(7) 119.9

C(20)-C(25) 1.383(3) C(25)-C(24)-C(23) 120.4(2)

C(20)-C(19) 1.484(3) C(25)-C(24)-H(24) 119.8

C(15)-H(15) 0.93 C(23)-C(24)-H(24) 119.8

C(2)-C(3) 1.390(3) C(25)-C(20)-C(21) 118.2(2)

C(5)-C(4) 1.378(3) C(25)-C(20)-C(19) 117.80(19)

C(18)-H(18) 0.93 C(21)-C(20)-C(19) 123.92(19)

C(4)-C(3) 1.368(4) C(16)-C(15)-C(14) 115.9(2)

C(4)-H(4) 0.93 C(16)-C(15)-H(15) 122

C(3)-H(3) 0.93 C(14)-C(15)-H(15) 122

C(25)-H(25) 0.93 O(1)-C(2)-C(7) 124.6(2)

C(1)-H(1A) 0.96 O(1)-C(2)-C(3) 114.5(2)

C(1)-H(1B) 0.96 C(7)-C(2)-C(3) 120.9(2)

C(1)-H(1C) 0.96 C(4)-C(5)-C(6) 122.2(2)

C(14)-O(4)-C(11) 106.20(17) C(4)-C(5)-O(2) 115.9(2)

C(2)-O(1)-C(1) 117.61(18) C(6)-C(5)-O(2) 121.9(2)

C(19)-N(1)-C(12) 121.23(19) C(17)-C(18)-C(13) 117.7(2)

C(19)-N(1)-H(1) 120.7(18) C(17)-C(18)-H(18) 121.2

C(12)-N(1)-H(1) 118.0(18) C(13)-C(18)-H(18) 121.2

C(12)-C(11)-O(4) 110.55(17) O(3)-C(10)-O(2) 117.3(2)

O(2)-C(10)-C(9) 117.2(2) O(3)-C(10)-C(9) 125.5(2)

C(3)-C(4)-C(5) 119.9(2) O(5)-C(19)-N(1) 120.9(2)

C(3)-C(4)-H(4) 120.1 O(5)-C(19)-C(20) 121.59(19)

C(5)-C(4)-H(4) 120.1 N(1)-C(19)-C(20) 117.51(19)

C(4)-C(3)-C(2) 119.3(2) O(1)-C(1)-H(1A) 109.5

C(4)-C(3)-H(3) 120.3 O(1)-C(1)-H(1B) 109.5

C(2)-C(3)-H(3) 120.3 H(1A)-C(1)-H(1B) 109.5

C(24)-C(25)-C(20) 121.0(2) O(1)-C(1)-H(1C) 109.5

C(24)-C(25)-H(25) 119.5 H(1A)-C(1)-H(1C) 109.5

C(20)-C(25)-H(25) 119.5 H(1B)-C(1)-H(1C) 109.5

Table 4. Anisotropic displacement parameters (Å2 × 103).

U11 U22 U33 U23 U13 U12

O(4) 34(1) 49(1)37(1) –2(1) –6(1)6(1)

O(3) 52(1)63(1)66(1) –17(1) 12(1)14(1)

O(1) 57(1)57(1)45(1) 13(1) 0(1) 12(1)

N(1) 32(1)34(1)36(1) –7(1) 2(1) 0(1)

C(11)34(1)34(1)34(1) 2(1) -4(1) 2(1)

C(6) 30(1)40(1)34(1) –2(1) 2(1) –7(1)

C(9) 37(1)43(1)41(1) –3(1) 2(1) 2(1)

O(2) 50(1)63(1)41(1) –10(1) 8(1) 12(1)

C(12)32(1)31(1)31(1) 2(1) 1(1) 2(1)

C(22)40(1) 46(1) 46(1) –9(1) –1(1) –7(1)

C(8) 29(1)34(1)37(1) –2(1) 4(1) –2(1)

C(21)40(1) 34(1) 39(1) –5(1) 4(1) 4(1)

C(17)86(2) 52(2) 29(1) –2(1) 1(1) –9(2)

C(23)33(1)59(2)53(2) 2(1) –4(1) 1(1)

C(13)45(1)28(1)31(1) 3(1) 1(1) –2(1)

C(14)44(2)35(1)36(1) 2(1) –5(1) 3(1)

C(16)87(2)50(2)38(1) 4(1) –22(2)–5(2)

C(7) 34(1)42(1)29(1) 2(1) 3(1) -4(1)

C(24)40(2)47(2)91(2) 4(2) –3(1)13(1)

O(5) 48(1)37(1)80(1) –16(1) –7(1)–2(1)

C(20)33(1)34(1)30(1) 0(1) 4(1) –1(1)

C(15)56(2)52(2)51(2) 2(1) –19(1)6(1)

C(2) 36(1)42(1)38(1) 5(1) 0(1) –3(1)

C(5) 35(1)52(1)39(1) –8(1) 7(1) 1(1)

C(18)58(2)42(1)32(1) 1(1) 7(1) –4(1)

C(10)35(1)48(1)49(1) –11(1) 6(1) 0(1)

C(4) 54(2)82(2)30(1) –1(1) 4(1) 4(2)

C(3) 49(2) 69(2) 34(1) 10(1) –2(1) –2(1)

C(25)44(2) 32(1) 76(2) –3(1) 5(1) 5(1)

C(19)37(1)32(1)33(1) 0(1) 4(1) –2(1)

C(1) 73(2)77(2)53(2) 8(1) 7(2) 35(2)

Table 5. Hydrogen coordinates (× 104) and isotropic dis-

placement parameters (Å2 × 103).

x y z U(eq)

H(9) 11545 513 967 48

H(22) 4432 709 1378 53

H(21) 6305 1044 1579 45

H(17) 9502 3334 4696 67

H(23) 3230 2531 1415 58

H(16) 11398 3138 4614 70

H(7) 8856 3917 634 42

H(24) 3901 4695 1648 71

H(15) 12256 2704 3397 64

H(18) 8390 3124 3570 53

H(4) 10107 2752 –1899 66

H(3) 8824 4478 –1751 61

H(25) 5753 5034 1879 61

H(1A) 6989 4738 346 101

H(1B) 6809 6276 117 101

H(1C) 7859 5840 611 101

H(1) 7970(20) 1660(30) 1489(16) 61(8)

G. ANURADHA ET AL. 111

Table 6. Torsion angles [˚].

C(14)-O(4)-C(11)-C(12) –1.4(2)

C(14)-O(4)-C(11)-C(8) –179.38(17)

O(4)-C(11)-C(12)-N(1) –171.91(19)

C(8)-C(11)-C(12)-N(1) 5.4(4)

O(4)-C(11)-C(12)-C(13) 1.1(2)

C(8)-C(11)-C(12)-C(13) 178.4(2)

C(19)-N(1)-C(12)-C(11) –135.3(2)

C(19)-N(1)-C(12)-C(13) 53.0(3)

C(10)-C(9)-C(8)-C(6) –1.8(3)

C(10)-C(9)-C(8)-C(11) –177.2(2)

C(5)-C(6)-C(8)-C(9) –1.6(3)

C(7)-C(6)-C(8)-C(9) –176.8(2)

C(5)-C(6)-C(8)-C(11) 173.7(2)

C(7)-C(6)-C(8)-C(11) –1.5(3)

C(12)-C(11)-C(8)-C(9) –138.6(3)

O(4)-C(11)-C(8)-C(9) 38.6(3)

C(12)-C(11)-C(8)-C(6) 46.1(3)

O(4)-C(11)-C(8)-C(6) –136.68(19)

C(23)-C(22)-C(21)-C(20) 0.5(4)

C(21)-C(22)-C(23)-C(24) 0.0(4)

C(11)-C(12)-C(13)-C(14) –0.3(2)

N(1)-C(12)-C(13)-C(14) 172.8(2)

C(11)-C(12)-C(13)-C(18) –177.7(2)

N(1)-C(12)-C(13)-C(18) –4.6(4)

C(18)-C(13)-C(14)-O(4) 177.31(18)

C(12)-C(13)-C(14)-O(4) –0.6(2)

C(18)-C(13)-C(14)-C(15) –1.6(3)

C(12)-C(13)-C(14)-C(15) –179.4(2)

C(11)-O(4)-C(14)-C(13) 1.2(2)

C(11)-O(4)-C(14)-C(15) –179.9(2)

C(18)-C(17)-C(16)-C(15) -0.4(4)

C(5)-C(6)-C(7)-C(2) 0.8(3)

C(8)-C(6)-C(7)-C(2) 176.0(2)

C(22)-C(23)-C(24)-C(25) –0.9(4)

C(22)-C(21)-C(20)-C(25) –0.1(3)

C(22)-C(21)-C(20)-C(19) 176.6(2)

C(17)-C(16)-C(15)-C(14) –0.8(4)

C(13)-C(14)-C(15)-C(16) 1.8(3)

O(4)-C(14)-C(15)-C(16) –176.9(2)

C(1)-O(1)-C(2)-C(7) –14.5(3)

C(1)-O(1)-C(2)-C(3) 167.6(2)

C(6)-C(7)-C(2)-O(1) –180.0(2)

C(6)-C(7)-C(2)-C(3) –2.2(3)

C(7)-C(6)-C(5)-C(4) 0.9(3)

C(8)-C(6)-C(5)-C(4) –174.7(2)

C(7)-C(6)-C(5)-O(2) 179.0(2)

C(8)-C(6)-C(5)-O(2) 3.4(3)

C(10)-O(2)-C(5)-C(4) 176.5(2)

C(10)-O(2)-C(5)-C(6) –1.7(3)

C(16)-C(17)-C(18)-C(13) 0.7(4)

C(14)-C(13)-C(18)-C(17) 0.3(3)

C(12)-C(13)-C(18)-C(17) 177.4(2)

C(5)-O(2)-C(10)-O(3) 178.2(2)

C(5)-O(2)-C(10)-C(9) –1.7(3)

C(8)-C(9)-C(10)-O(3) –176.4(2)

Continue

C(8)-C(9)-C(10)-O(2) 3.5(3)

C(6)-C(5)-C(4)-C(3) –1.1(4)

O(2)-C(5)-C(4)-C(3) –179.3(2)

C(5)-C(4)-C(3)-C(2) –0.3(4)

O(1)-C(2)-C(3)-C(4) 180.0(2)

C(7)-C(2)-C(3)-C(4) 2.0(4)

C(23)-C(24)-C(25)-C(20) 1.2(4)

C(21)-C(20)-C(25)-C(24) –0.7(4)

C(19)-C(20)-C(25)-C(24) –177.7(2)

C(12)-N(1)-C(19)-O(5) 9.1(3)

C(12)-N(1)-C(19)-C(20) –171.69(18)

C(25)-C(20)-C(19)-O(5) 12.3(3)

C(21)-C(20)-C(19)-O(5) –164.5(2)

C(25)-C(20)-C(19)-N(1) –166.9(2)

C(21)-C(20)-C(19)-N(1) 16.3(3)

Table 7. Hydrogen bonds [Å and ˚], Cg4 is the centroid of

the C13-C18 ring; Cg5 is the centroid of the C20-C25 ring.

D-H...A d(D-H) d(H...A) d(D...A)<(DHA)

C(7)-H(7)…N1 0.93 2.52 3.184(3)128

N(1)-H(1)...O (3)i 0.87(3) 2.19(3) 3.003(3)156(2)

C(4)-H(4)…Cg(5)ii 0.93 2.54 3.427(3)160

C(22)-H(22)…Cg(4)iii 0.93 2.78 3.608(3)149

Note: Symmetry transformations used to generate equivalent atoms: (i)1 – x +

2, –y, –z; (ii)1/2 + x,1/2 – y, –1/2 + z; (iii) 3/2 – x, –1/2 + y, 1/2 – z.

The authenticity of the compound has been established

from the obtained peak values.

4. Conclusion

The N-substituted benzamide derivatives have been re-

viewed for antibacterial, anti-inflammatory, analgesic

and antiulcer actions. Pharmaceutical compositions of

amide derivatives are used as, therapeutic agents for hy-

pertension, angina, pectoris, asthma, renal and peripheral

circulatory disturbances and inhibitors of vasospasm. The

compounds are useful where cell death is due to trauma,

viral infection, neurodegenerative disorder, cardiovascu-

lar disease, immune deficiency disorder, autoimmune

disorder, renal disease, syndromes or pancreatitis. Sub-

stituted benzamides are acting as inhibitors of HIV pro-

tease [13]. These reported points are very useful to un-

derstand the benefit functions of the substituted ben-

zamides in general. The title compound belongs to a

class of 4-2’-benzofuranyl coumarins, the methoxy de-

rivatives of which have exhibited potential anti inflam-

matory activity [14]. Further the 6-methoxy group is well

known to undergo biotransformation to the correspond-

ing 6-hydroxy coumarin possessing a phenolic group

which enhances its ability of binding with biomolecules

which is the basis of its pharmacological activity. The

N-benzoyl moiety will also undergo cleavage to generate

G. ANURADHA ET AL.

112

(a)

(b)

(c)

Figure 3. (a): Formation of centrosymmetric dimers; π-π

interaction shown as dotted line; (b): Part of the crystal

structure of the compound, showing formation of a centro-

symmetric R22(16) dimmer; (c): Packing diagram, showing

infinite chains running along the b-axis direction. Hydrogen

bonds are shown as dashed lines. For the sake of clarity H

atoms not involved in the motif shown have been omitted.

a potential pharmacophoric amino group. The stereo-

chemistry of the amide linkage has been established by

present X-ray studies which is not possible by the con-

ventional spectral studies. The title compound is air-sta-

ble in the solid state, crystallized from ethanol and in-

soluble in water. The authenticity of the compound has

been established by IR technique. The crystallographic

Figure 4. Packing diagram and H bonding geometry along

the a-axis [symmetry code: 2 – x, –y, –z]. H atoms not in-

volved in these interactions have been omitted for clarity.

investigation carried out was quite interesting by the

zigzag packing of the dimers formed due to the two dif-

ferent orientations (Figures 2(a) and (b)) of the benzoyl

group and the benzofuran ring. The amide was adopting

the S-trans configuration and the packing diagram re-

vealed a rare type of dimeric linkage between the lactone

carbonyl and the amide N—H bond. The compound

characterized can be essential in medicinal and biological

applications. The title structure may be important from a

medicinal point of view as well as their widespread bio-

logical significance. The structure may be useful for fur-

ther investigation on the mechanism, potential activity,

optimal reaction condition etc.

5. Acknowledgements

The authors thank the Sophisticated Analytical Instru-

ment Facility, IIT Madras, Chennai-36, for the data col-

lection.

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