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The title compound, C14H10ClNO3, was synthesized by reacting stoichiometric amounts of anthranilic acid and 2-chloro­benzoyl chloride at ambient temperature. The dihedral angle between the two rings is 63.19 (12)°. The mol­ecules are stabilized by four intra­molecular hydrogen bonds, two C—H...O, one N—H...O and one N—H...Cl. Inter­molecular O—H...O hydrogen bonding links the mol­ecules in parallel layers along the ac plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044352/kp2128sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044352/kp2128Isup2.hkl
Contains datablock I

CCDC reference: 663798

Key indicators

  • Single-crystal X-ray study
  • T = 283 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.109
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H10 Cl N O3
0 ALERT level A = In general: serious problem 0 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The molecules designed on anthranilic acid scaffold for new anticancer drugs have attracted great interest in recent years (Roe et al., 1999; Mistry et al., 2001; Manley et al., 2002; Levin et al., 2001). Among them there are: Tranilast (N-[3,4-dimethoxycinnamoyl]-anthranilic acid), a well known anti-allergic drug (Isaji et al., 1997); farnesyl anthranilate suppresses the growth of murine melanomas in in vivo and in vitro (Mo et al.,2000); the anthranilamide PD 184352 (CI-1040), developed by Parke-Davis, is an inhibitor of both mitogen activated extracellular kinases (MEK1 and MEK2). In vivo, PD 184352 was shown to inhibit the growth of colon and pancreatic tumors (Sebolt-Leopold et al., 1999). Therefore, precedent examples of drugs with anthranilic scaffold stimulated us to continue our research with anticancer activity based on the anthranilic acid scaffold. The title compound I, is expected to possess some interesting biological activities. The present paper describes the X-ray structure analysis that will be of help in molecular modelling and future drug design.

The title compound (I), was synthesized in moderate yield (Pavlidis & Perry, 1994) by reacting stichiometric amounts of anthranilic acid and 2-chlorobenzoylchloride at ambient temperature, using pyridine as a solvent. All bond lengths in the title compound (I) show normal values (Allen et al., 1987). The two aromatic rings are completely planar and the acute angle between them is 63.19 (12)°. The title compound (I) (Fig. 1) shows intramolecular N—H···Cl, N—H···O and C—H···O hydrogen bonds generating three S(6) graph set motifs, while C—H···O hydrogen bond generates an S(5) graph sett motif (Bernstein et al., 1995). These intramolecular hydrogen bonds influence the widening and shrinkage (from 120°) of the the exocyclic angles C7—N1—C8 [129.7 (2) °] and N1—C7—C1 [116.3 (2) °], respectively. An intermolecular O—H···O hydrogen bond keeps molecules in parallel layers along the c axis (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Isaji et al. (1997); Levin et al. (2001); Manley et al. (2002); Mistry et al. (2001); Mo et al. (2000); Pavlidis & Perry (1994); Roe et al. (1999); Sebolt-Leopold et al. (1999).

Experimental top

To a solution of anthranilic acid (1.0 g, 7.29 mmol) in pyridine (25 ml) was added 2-chlorobenzoylchloride (1.27 g, 7.29 mmol). The mixture was shaken for 5 min and keep at room temperature for a further 25 min with occasional shaking. The reaction mixture was poured into ice water (200 ml) and stirred for a few minutes; the precipitate was filtered off; the residue was washed with cold water (3x 60 ml). The title compound (I), was crystallized from dichloromethane in 62% overall yield (1.24 g).

Refinement top

H atoms bonded to oxygen or nitrogen were refined freely to account for inter- and intra-molecular hydrogen bonds. However, the rest of atoms were placed in calculated positions with a C—H distances in 0.93 Å and Uiso(H) = 1.5Ueq(N) for amide H and 1.2Ueq(C) for others.

Structure description top

The molecules designed on anthranilic acid scaffold for new anticancer drugs have attracted great interest in recent years (Roe et al., 1999; Mistry et al., 2001; Manley et al., 2002; Levin et al., 2001). Among them there are: Tranilast (N-[3,4-dimethoxycinnamoyl]-anthranilic acid), a well known anti-allergic drug (Isaji et al., 1997); farnesyl anthranilate suppresses the growth of murine melanomas in in vivo and in vitro (Mo et al.,2000); the anthranilamide PD 184352 (CI-1040), developed by Parke-Davis, is an inhibitor of both mitogen activated extracellular kinases (MEK1 and MEK2). In vivo, PD 184352 was shown to inhibit the growth of colon and pancreatic tumors (Sebolt-Leopold et al., 1999). Therefore, precedent examples of drugs with anthranilic scaffold stimulated us to continue our research with anticancer activity based on the anthranilic acid scaffold. The title compound I, is expected to possess some interesting biological activities. The present paper describes the X-ray structure analysis that will be of help in molecular modelling and future drug design.

The title compound (I), was synthesized in moderate yield (Pavlidis & Perry, 1994) by reacting stichiometric amounts of anthranilic acid and 2-chlorobenzoylchloride at ambient temperature, using pyridine as a solvent. All bond lengths in the title compound (I) show normal values (Allen et al., 1987). The two aromatic rings are completely planar and the acute angle between them is 63.19 (12)°. The title compound (I) (Fig. 1) shows intramolecular N—H···Cl, N—H···O and C—H···O hydrogen bonds generating three S(6) graph set motifs, while C—H···O hydrogen bond generates an S(5) graph sett motif (Bernstein et al., 1995). These intramolecular hydrogen bonds influence the widening and shrinkage (from 120°) of the the exocyclic angles C7—N1—C8 [129.7 (2) °] and N1—C7—C1 [116.3 (2) °], respectively. An intermolecular O—H···O hydrogen bond keeps molecules in parallel layers along the c axis (Fig. 2).

For related literature, see: Allen et al. (1987); Bernstein et al. (1995); Isaji et al. (1997); Levin et al. (2001); Manley et al. (2002); Mistry et al. (2001); Mo et al. (2000); Pavlidis & Perry (1994); Roe et al. (1999); Sebolt-Leopold et al. (1999).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing the 50% probability displacement ellipsoids and the atom-numbering scheme. A dashed lines indicate the intramolecular hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of (I), viewed down the c axis.
2-(2-Chlorobenzamido)benzoic acid top
Crystal data top
C14H10ClNO3F(000) = 568
Mr = 275.68Dx = 1.467 Mg m3
Monoclinic, P21/cMelting point: 379 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.7808 (7) ÅCell parameters from 1776 reflections
b = 15.9978 (11) Åθ = 2.6–27.2°
c = 7.2944 (5) ŵ = 0.31 mm1
β = 97.122 (1)°T = 283 K
V = 1248.35 (15) Å3Block, colourless
Z = 40.35 × 0.33 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2188 independent reflections
Radiation source: fine-focus sealed tube1725 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω scansh = 1112
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1918
Tmin = 0.900, Tmax = 0.976l = 88
6230 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.495P]
where P = (Fo2 + 2Fc2)/3
2188 reflections(Δ/σ)max < 0.001
180 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C14H10ClNO3V = 1248.35 (15) Å3
Mr = 275.68Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.7808 (7) ŵ = 0.31 mm1
b = 15.9978 (11) ÅT = 283 K
c = 7.2944 (5) Å0.35 × 0.33 × 0.08 mm
β = 97.122 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2188 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1725 reflections with I > 2σ(I)
Tmin = 0.900, Tmax = 0.976Rint = 0.026
6230 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.23 e Å3
2188 reflectionsΔρmin = 0.32 e Å3
180 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.74177 (7)0.65886 (5)0.01354 (10)0.0683 (3)
O10.97574 (15)0.51058 (10)0.2858 (3)0.0541 (5)
N10.98919 (18)0.64494 (13)0.1894 (3)0.0415 (5)
O31.15398 (17)0.87729 (11)0.0861 (3)0.0559 (5)
O20.97761 (16)0.80934 (10)0.1690 (3)0.0584 (5)
C20.7035 (2)0.62740 (15)0.2423 (3)0.0433 (6)
C30.5802 (2)0.63371 (18)0.3190 (4)0.0553 (7)
H3A0.52110.65630.25060.066*
C40.5451 (2)0.60673 (19)0.4956 (4)0.0597 (8)
H4A0.46190.61060.54660.072*
C50.6319 (2)0.57403 (18)0.5981 (4)0.0560 (7)
H5A0.60790.55670.71900.067*
C60.7549 (2)0.56701 (16)0.5213 (3)0.0468 (6)
H6A0.81320.54420.59100.056*
C10.7934 (2)0.59333 (13)0.3420 (3)0.0378 (6)
C70.9274 (2)0.57911 (14)0.2679 (3)0.0387 (6)
C81.1139 (2)0.65116 (14)0.1069 (3)0.0367 (5)
C131.1887 (2)0.58132 (15)0.0640 (3)0.0458 (6)
H13A1.15690.52810.09060.055*
C121.3100 (2)0.59119 (17)0.0180 (4)0.0526 (7)
H12A1.35960.54420.04600.063*
C111.3593 (2)0.66937 (17)0.0593 (4)0.0507 (7)
H11A1.44140.67540.11380.061*
C101.2851 (2)0.73829 (16)0.0186 (3)0.0439 (6)
H10A1.31790.79110.04790.053*
C91.1627 (2)0.73155 (14)0.0651 (3)0.0346 (5)
C141.0881 (2)0.80848 (14)0.1115 (3)0.0389 (6)
H1N10.954 (2)0.6908 (15)0.193 (3)0.039 (7)*
H1O31.107 (3)0.920 (2)0.122 (4)0.080 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0647 (5)0.0891 (6)0.0524 (4)0.0047 (4)0.0126 (3)0.0174 (4)
O10.0418 (10)0.0363 (10)0.0818 (14)0.0031 (8)0.0015 (9)0.0151 (9)
N10.0367 (11)0.0271 (11)0.0585 (14)0.0046 (9)0.0022 (9)0.0054 (9)
O30.0494 (11)0.0327 (10)0.0819 (14)0.0050 (9)0.0063 (10)0.0057 (9)
O20.0420 (11)0.0351 (10)0.0942 (15)0.0026 (8)0.0064 (10)0.0016 (9)
C20.0447 (14)0.0401 (14)0.0458 (14)0.0017 (11)0.0087 (11)0.0007 (11)
C30.0434 (15)0.0641 (18)0.0602 (18)0.0108 (13)0.0132 (13)0.0032 (14)
C40.0383 (15)0.074 (2)0.0647 (19)0.0074 (14)0.0006 (13)0.0034 (15)
C50.0490 (17)0.0667 (18)0.0503 (16)0.0018 (14)0.0020 (13)0.0028 (14)
C60.0437 (15)0.0478 (15)0.0494 (15)0.0000 (11)0.0072 (12)0.0064 (12)
C10.0392 (13)0.0284 (12)0.0460 (14)0.0014 (10)0.0065 (11)0.0000 (10)
C70.0400 (14)0.0319 (13)0.0447 (14)0.0017 (10)0.0073 (11)0.0015 (10)
C80.0348 (13)0.0384 (13)0.0372 (13)0.0022 (10)0.0050 (10)0.0003 (10)
C130.0488 (15)0.0356 (13)0.0512 (15)0.0040 (11)0.0010 (12)0.0019 (11)
C120.0435 (15)0.0531 (17)0.0591 (17)0.0150 (13)0.0017 (12)0.0053 (13)
C110.0338 (14)0.0629 (18)0.0529 (16)0.0012 (12)0.0042 (11)0.0054 (13)
C100.0422 (14)0.0438 (14)0.0449 (14)0.0070 (11)0.0024 (11)0.0035 (11)
C90.0353 (12)0.0365 (13)0.0323 (12)0.0002 (10)0.0058 (9)0.0017 (10)
C140.0401 (14)0.0352 (13)0.0410 (14)0.0010 (11)0.0033 (11)0.0013 (10)
Geometric parameters (Å, º) top
Cl1—C21.743 (3)C5—H5A0.9300
O1—C71.228 (3)C6—C11.388 (3)
N1—C71.336 (3)C6—H6A0.9300
N1—C81.407 (3)C1—C71.496 (3)
N1—H1N10.83 (2)C8—C131.390 (3)
O3—C141.311 (3)C8—C91.408 (3)
O3—H1O30.87 (3)C13—C121.378 (3)
O2—C141.213 (3)C13—H13A0.9300
C2—C31.381 (4)C12—C111.377 (4)
C2—C11.393 (3)C12—H12A0.9300
C3—C41.367 (4)C11—C101.373 (3)
C3—H3A0.9300C11—H11A0.9300
C4—C51.372 (4)C10—C91.388 (3)
C4—H4A0.9300C10—H10A0.9300
C5—C61.379 (3)C9—C141.486 (3)
C7—N1—C8129.7 (2)O1—C7—C1120.1 (2)
C7—N1—H1N1118.8 (16)N1—C7—C1116.3 (2)
C8—N1—H1N1111.4 (16)C13—C8—N1122.4 (2)
C14—O3—H1O3109 (2)C13—C8—C9119.7 (2)
C3—C2—C1121.0 (2)N1—C8—C9117.9 (2)
C3—C2—Cl1117.9 (2)C12—C13—C8119.9 (2)
C1—C2—Cl1121.02 (18)C12—C13—H13A120.1
C4—C3—C2119.9 (3)C8—C13—H13A120.1
C4—C3—H3A120.0C11—C12—C13121.2 (2)
C2—C3—H3A120.0C11—C12—H12A119.4
C3—C4—C5120.4 (2)C13—C12—H12A119.4
C3—C4—H4A119.8C10—C11—C12118.9 (2)
C5—C4—H4A119.8C10—C11—H11A120.5
C4—C5—C6119.8 (3)C12—C11—H11A120.5
C4—C5—H5A120.1C11—C10—C9122.0 (2)
C6—C5—H5A120.1C11—C10—H10A119.0
C5—C6—C1121.2 (2)C9—C10—H10A119.0
C5—C6—H6A119.4C10—C9—C8118.4 (2)
C1—C6—H6A119.4C10—C9—C14119.6 (2)
C6—C1—C2117.7 (2)C8—C9—C14122.0 (2)
C6—C1—C7117.2 (2)O2—C14—O3122.1 (2)
C2—C1—C7125.0 (2)O2—C14—C9124.7 (2)
O1—C7—N1123.6 (2)O3—C14—C9113.3 (2)
C1—C2—C3—C40.4 (4)C7—N1—C8—C1312.4 (4)
Cl1—C2—C3—C4177.5 (2)C7—N1—C8—C9168.4 (2)
C2—C3—C4—C50.6 (4)N1—C8—C13—C12179.5 (2)
C3—C4—C5—C61.1 (4)C9—C8—C13—C120.4 (4)
C4—C5—C6—C10.7 (4)C8—C13—C12—C110.2 (4)
C5—C6—C1—C20.2 (4)C13—C12—C11—C100.4 (4)
C5—C6—C1—C7177.0 (2)C12—C11—C10—C90.9 (4)
C3—C2—C1—C60.8 (4)C11—C10—C9—C80.7 (4)
Cl1—C2—C1—C6177.76 (18)C11—C10—C9—C14178.0 (2)
C3—C2—C1—C7176.2 (2)C13—C8—C9—C100.0 (3)
Cl1—C2—C1—C70.8 (3)N1—C8—C9—C10179.2 (2)
C8—N1—C7—O12.8 (4)C13—C8—C9—C14178.6 (2)
C8—N1—C7—C1179.4 (2)N1—C8—C9—C142.2 (3)
C6—C1—C7—O147.6 (3)C10—C9—C14—O2173.0 (2)
C2—C1—C7—O1129.3 (3)C8—C9—C14—O28.4 (4)
C6—C1—C7—N1130.3 (2)C10—C9—C14—O37.6 (3)
C2—C1—C7—N152.8 (3)C8—C9—C14—O3171.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···Cl10.82 (2)2.82 (2)3.108 (2)103 (3)
N1—H1N1···O20.82 (2)1.92 (2)2.638 (3)145 (2)
O3—H1O3···O1i0.87 (3)1.79 (3)2.656 (3)173 (3)
C10—H10A···O30.932.362.694 (3)101
C13—H13A···O10.932.292.872 (3)120
Symmetry code: (i) x+2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC14H10ClNO3
Mr275.68
Crystal system, space groupMonoclinic, P21/c
Temperature (K)283
a, b, c (Å)10.7808 (7), 15.9978 (11), 7.2944 (5)
β (°) 97.122 (1)
V3)1248.35 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.35 × 0.33 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.900, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
6230, 2188, 1725
Rint0.026
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.109, 1.07
No. of reflections2188
No. of parameters180
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.32

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···Cl10.82 (2)2.82 (2)3.108 (2)103 (3)
N1—H1N1···O20.82 (2)1.92 (2)2.638 (3)145 (2)
O3—H1O3···O1i0.87 (3)1.79 (3)2.656 (3)173 (3)
C10—H10A···O30.932.3562.694 (3)101
C13—H13A···O10.932.2872.872 (3)120
Symmetry code: (i) x+2, y+1/2, z1/2.
 

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