Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044352/kp2128sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044352/kp2128Isup2.hkl |
CCDC reference: 663798
Key indicators
- Single-crystal X-ray study
- T = 283 K
- Mean (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
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).
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).
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.
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).
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).
C14H10ClNO3 | F(000) = 568 |
Mr = 275.68 | Dx = 1.467 Mg m−3 |
Monoclinic, P21/c | Melting point: 379 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7808 (7) Å | Cell parameters from 1776 reflections |
b = 15.9978 (11) Å | θ = 2.6–27.2° |
c = 7.2944 (5) Å | µ = 0.31 mm−1 |
β = 97.122 (1)° | T = 283 K |
V = 1248.35 (15) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.33 × 0.08 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2188 independent reflections |
Radiation source: fine-focus sealed tube | 1725 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −19→18 |
Tmin = 0.900, Tmax = 0.976 | l = −8→8 |
6230 measured reflections |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H 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 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C14H10ClNO3 | V = 1248.35 (15) Å3 |
Mr = 275.68 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.7808 (7) Å | µ = 0.31 mm−1 |
b = 15.9978 (11) Å | T = 283 K |
c = 7.2944 (5) Å | 0.35 × 0.33 × 0.08 mm |
β = 97.122 (1)° |
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 = 0.976 | Rint = 0.026 |
6230 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.23 e Å−3 |
2188 reflections | Δρmin = −0.32 e Å−3 |
180 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.74177 (7) | 0.65886 (5) | −0.01354 (10) | 0.0683 (3) | |
O1 | 0.97574 (15) | 0.51058 (10) | −0.2858 (3) | 0.0541 (5) | |
N1 | 0.98919 (18) | 0.64494 (13) | −0.1894 (3) | 0.0415 (5) | |
O3 | 1.15398 (17) | 0.87729 (11) | −0.0861 (3) | 0.0559 (5) | |
O2 | 0.97761 (16) | 0.80934 (10) | −0.1690 (3) | 0.0584 (5) | |
C2 | 0.7035 (2) | 0.62740 (15) | −0.2423 (3) | 0.0433 (6) | |
C3 | 0.5802 (2) | 0.63371 (18) | −0.3190 (4) | 0.0553 (7) | |
H3A | 0.5211 | 0.6563 | −0.2506 | 0.066* | |
C4 | 0.5451 (2) | 0.60673 (19) | −0.4956 (4) | 0.0597 (8) | |
H4A | 0.4619 | 0.6106 | −0.5466 | 0.072* | |
C5 | 0.6319 (2) | 0.57403 (18) | −0.5981 (4) | 0.0560 (7) | |
H5A | 0.6079 | 0.5567 | −0.7190 | 0.067* | |
C6 | 0.7549 (2) | 0.56701 (16) | −0.5213 (3) | 0.0468 (6) | |
H6A | 0.8132 | 0.5442 | −0.5910 | 0.056* | |
C1 | 0.7934 (2) | 0.59333 (13) | −0.3420 (3) | 0.0378 (6) | |
C7 | 0.9274 (2) | 0.57911 (14) | −0.2679 (3) | 0.0387 (6) | |
C8 | 1.1139 (2) | 0.65116 (14) | −0.1069 (3) | 0.0367 (5) | |
C13 | 1.1887 (2) | 0.58132 (15) | −0.0640 (3) | 0.0458 (6) | |
H13A | 1.1569 | 0.5281 | −0.0906 | 0.055* | |
C12 | 1.3100 (2) | 0.59119 (17) | 0.0180 (4) | 0.0526 (7) | |
H12A | 1.3596 | 0.5442 | 0.0460 | 0.063* | |
C11 | 1.3593 (2) | 0.66937 (17) | 0.0593 (4) | 0.0507 (7) | |
H11A | 1.4414 | 0.6754 | 0.1138 | 0.061* | |
C10 | 1.2851 (2) | 0.73829 (16) | 0.0186 (3) | 0.0439 (6) | |
H10A | 1.3179 | 0.7911 | 0.0479 | 0.053* | |
C9 | 1.1627 (2) | 0.73155 (14) | −0.0651 (3) | 0.0346 (5) | |
C14 | 1.0881 (2) | 0.80848 (14) | −0.1115 (3) | 0.0389 (6) | |
H1N1 | 0.954 (2) | 0.6908 (15) | −0.193 (3) | 0.039 (7)* | |
H1O3 | 1.107 (3) | 0.920 (2) | −0.122 (4) | 0.080 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0647 (5) | 0.0891 (6) | 0.0524 (4) | 0.0047 (4) | 0.0126 (3) | −0.0174 (4) |
O1 | 0.0418 (10) | 0.0363 (10) | 0.0818 (14) | 0.0031 (8) | −0.0015 (9) | −0.0151 (9) |
N1 | 0.0367 (11) | 0.0271 (11) | 0.0585 (14) | 0.0046 (9) | −0.0022 (9) | −0.0054 (9) |
O3 | 0.0494 (11) | 0.0327 (10) | 0.0819 (14) | −0.0050 (9) | −0.0063 (10) | 0.0057 (9) |
O2 | 0.0420 (11) | 0.0351 (10) | 0.0942 (15) | 0.0026 (8) | −0.0064 (10) | −0.0016 (9) |
C2 | 0.0447 (14) | 0.0401 (14) | 0.0458 (14) | 0.0017 (11) | 0.0087 (11) | 0.0007 (11) |
C3 | 0.0434 (15) | 0.0641 (18) | 0.0602 (18) | 0.0108 (13) | 0.0132 (13) | 0.0032 (14) |
C4 | 0.0383 (15) | 0.074 (2) | 0.0647 (19) | 0.0074 (14) | −0.0006 (13) | 0.0034 (15) |
C5 | 0.0490 (17) | 0.0667 (18) | 0.0503 (16) | 0.0018 (14) | −0.0020 (13) | −0.0028 (14) |
C6 | 0.0437 (15) | 0.0478 (15) | 0.0494 (15) | 0.0000 (11) | 0.0072 (12) | −0.0064 (12) |
C1 | 0.0392 (13) | 0.0284 (12) | 0.0460 (14) | −0.0014 (10) | 0.0065 (11) | 0.0000 (10) |
C7 | 0.0400 (14) | 0.0319 (13) | 0.0447 (14) | 0.0017 (10) | 0.0073 (11) | −0.0015 (10) |
C8 | 0.0348 (13) | 0.0384 (13) | 0.0372 (13) | 0.0022 (10) | 0.0050 (10) | −0.0003 (10) |
C13 | 0.0488 (15) | 0.0356 (13) | 0.0512 (15) | 0.0040 (11) | −0.0010 (12) | −0.0019 (11) |
C12 | 0.0435 (15) | 0.0531 (17) | 0.0591 (17) | 0.0150 (13) | −0.0017 (12) | 0.0053 (13) |
C11 | 0.0338 (14) | 0.0629 (18) | 0.0529 (16) | 0.0012 (12) | −0.0042 (11) | 0.0054 (13) |
C10 | 0.0422 (14) | 0.0438 (14) | 0.0449 (14) | −0.0070 (11) | 0.0024 (11) | 0.0035 (11) |
C9 | 0.0353 (12) | 0.0365 (13) | 0.0323 (12) | 0.0002 (10) | 0.0058 (9) | 0.0017 (10) |
C14 | 0.0401 (14) | 0.0352 (13) | 0.0410 (14) | −0.0010 (11) | 0.0033 (11) | −0.0013 (10) |
Cl1—C2 | 1.743 (3) | C5—H5A | 0.9300 |
O1—C7 | 1.228 (3) | C6—C1 | 1.388 (3) |
N1—C7 | 1.336 (3) | C6—H6A | 0.9300 |
N1—C8 | 1.407 (3) | C1—C7 | 1.496 (3) |
N1—H1N1 | 0.83 (2) | C8—C13 | 1.390 (3) |
O3—C14 | 1.311 (3) | C8—C9 | 1.408 (3) |
O3—H1O3 | 0.87 (3) | C13—C12 | 1.378 (3) |
O2—C14 | 1.213 (3) | C13—H13A | 0.9300 |
C2—C3 | 1.381 (4) | C12—C11 | 1.377 (4) |
C2—C1 | 1.393 (3) | C12—H12A | 0.9300 |
C3—C4 | 1.367 (4) | C11—C10 | 1.373 (3) |
C3—H3A | 0.9300 | C11—H11A | 0.9300 |
C4—C5 | 1.372 (4) | C10—C9 | 1.388 (3) |
C4—H4A | 0.9300 | C10—H10A | 0.9300 |
C5—C6 | 1.379 (3) | C9—C14 | 1.486 (3) |
C7—N1—C8 | 129.7 (2) | O1—C7—C1 | 120.1 (2) |
C7—N1—H1N1 | 118.8 (16) | N1—C7—C1 | 116.3 (2) |
C8—N1—H1N1 | 111.4 (16) | C13—C8—N1 | 122.4 (2) |
C14—O3—H1O3 | 109 (2) | C13—C8—C9 | 119.7 (2) |
C3—C2—C1 | 121.0 (2) | N1—C8—C9 | 117.9 (2) |
C3—C2—Cl1 | 117.9 (2) | C12—C13—C8 | 119.9 (2) |
C1—C2—Cl1 | 121.02 (18) | C12—C13—H13A | 120.1 |
C4—C3—C2 | 119.9 (3) | C8—C13—H13A | 120.1 |
C4—C3—H3A | 120.0 | C11—C12—C13 | 121.2 (2) |
C2—C3—H3A | 120.0 | C11—C12—H12A | 119.4 |
C3—C4—C5 | 120.4 (2) | C13—C12—H12A | 119.4 |
C3—C4—H4A | 119.8 | C10—C11—C12 | 118.9 (2) |
C5—C4—H4A | 119.8 | C10—C11—H11A | 120.5 |
C4—C5—C6 | 119.8 (3) | C12—C11—H11A | 120.5 |
C4—C5—H5A | 120.1 | C11—C10—C9 | 122.0 (2) |
C6—C5—H5A | 120.1 | C11—C10—H10A | 119.0 |
C5—C6—C1 | 121.2 (2) | C9—C10—H10A | 119.0 |
C5—C6—H6A | 119.4 | C10—C9—C8 | 118.4 (2) |
C1—C6—H6A | 119.4 | C10—C9—C14 | 119.6 (2) |
C6—C1—C2 | 117.7 (2) | C8—C9—C14 | 122.0 (2) |
C6—C1—C7 | 117.2 (2) | O2—C14—O3 | 122.1 (2) |
C2—C1—C7 | 125.0 (2) | O2—C14—C9 | 124.7 (2) |
O1—C7—N1 | 123.6 (2) | O3—C14—C9 | 113.3 (2) |
C1—C2—C3—C4 | −0.4 (4) | C7—N1—C8—C13 | −12.4 (4) |
Cl1—C2—C3—C4 | −177.5 (2) | C7—N1—C8—C9 | 168.4 (2) |
C2—C3—C4—C5 | −0.6 (4) | N1—C8—C13—C12 | −179.5 (2) |
C3—C4—C5—C6 | 1.1 (4) | C9—C8—C13—C12 | −0.4 (4) |
C4—C5—C6—C1 | −0.7 (4) | C8—C13—C12—C11 | 0.2 (4) |
C5—C6—C1—C2 | −0.2 (4) | C13—C12—C11—C10 | 0.4 (4) |
C5—C6—C1—C7 | 177.0 (2) | C12—C11—C10—C9 | −0.9 (4) |
C3—C2—C1—C6 | 0.8 (4) | C11—C10—C9—C8 | 0.7 (4) |
Cl1—C2—C1—C6 | 177.76 (18) | C11—C10—C9—C14 | −178.0 (2) |
C3—C2—C1—C7 | −176.2 (2) | C13—C8—C9—C10 | 0.0 (3) |
Cl1—C2—C1—C7 | 0.8 (3) | N1—C8—C9—C10 | 179.2 (2) |
C8—N1—C7—O1 | −2.8 (4) | C13—C8—C9—C14 | 178.6 (2) |
C8—N1—C7—C1 | 179.4 (2) | N1—C8—C9—C14 | −2.2 (3) |
C6—C1—C7—O1 | −47.6 (3) | C10—C9—C14—O2 | −173.0 (2) |
C2—C1—C7—O1 | 129.3 (3) | C8—C9—C14—O2 | 8.4 (4) |
C6—C1—C7—N1 | 130.3 (2) | C10—C9—C14—O3 | 7.6 (3) |
C2—C1—C7—N1 | −52.8 (3) | C8—C9—C14—O3 | −171.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···Cl1 | 0.82 (2) | 2.82 (2) | 3.108 (2) | 103 (3) |
N1—H1N1···O2 | 0.82 (2) | 1.92 (2) | 2.638 (3) | 145 (2) |
O3—H1O3···O1i | 0.87 (3) | 1.79 (3) | 2.656 (3) | 173 (3) |
C10—H10A···O3 | 0.93 | 2.36 | 2.694 (3) | 101 |
C13—H13A···O1 | 0.93 | 2.29 | 2.872 (3) | 120 |
Symmetry code: (i) −x+2, y+1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H10ClNO3 |
Mr | 275.68 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 283 |
a, b, c (Å) | 10.7808 (7), 15.9978 (11), 7.2944 (5) |
β (°) | 97.122 (1) |
V (Å3) | 1248.35 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.35 × 0.33 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.900, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6230, 2188, 1725 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.109, 1.07 |
No. of reflections | 2188 |
No. of parameters | 180 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.32 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···Cl1 | 0.82 (2) | 2.82 (2) | 3.108 (2) | 103 (3) |
N1—H1N1···O2 | 0.82 (2) | 1.92 (2) | 2.638 (3) | 145 (2) |
O3—H1O3···O1i | 0.87 (3) | 1.79 (3) | 2.656 (3) | 173 (3) |
C10—H10A···O3 | 0.93 | 2.356 | 2.694 (3) | 101 |
C13—H13A···O1 | 0.93 | 2.287 | 2.872 (3) | 120 |
Symmetry code: (i) −x+2, y+1/2, −z−1/2. |
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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).