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Indian Journal of Forensic Medicine & Toxicology

Comparative x-ray structure analysis of systemic fungicides â-4(-chlorophenoxy)-á-(1,1dimethylethyl))1H-1,2,4-triazole-1-ethanol and 1-(4-chlorophenoxy) 3,3-dimethyl-1- H(1,2,4-triazole-1-Y-1)2-butanone

Author(s): Jyotsna Chauhan

Vol. 2, No. 2 (2008-07 - 2008-12)

Jyotsna Chauhan

Lecturer, Department of physics, Rajeev Gandhi Technical University, Bhopal

Abstract

The unit cell parameters of â-4( Chlorophenoxy)á- (1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol are a = 8. 130(2) Å b = 16. 790(2) Å c=21. 990Å. á=90Ú b=92.52(1) Ú ä=90Ú. The space group is determined to be P21/n. The measured density is 1. 3215g/cm3 and calculated density is 1. 3102g/cm3. The average bond distances of C-H and N-H types are 0. 96(2)Å and 0. 90(1)Å respectively. The Unit cell parameter of 1-(4-Chlorophenoxy) 3,3-dimethyl-1- H(1,2,4- triazole-1-Y-1)2-butanone are a=8.16(10) Å, b=16.81(3) Å c=22 05(2) Å ,á=90Ú b=92. 37 (1)Ú ä=90Ú and Z=8 and space group is determined P21/n. The measured density is 1. 291́g/cm3 and calculated density is 1. 295́g/cm3. We can see that although there are different chemical groups attached with both the compounds(Ethanol group is attached with one systemic fungicides while butanone with another.) but their cell parameters and average bond distances and angles are nearly equal. Thus we determine the three-dimensional structure, molecular dimensions, molecular geometry, electronic structure and the conformation of fungicides and analyze their crystal structures also. Then correlate the chemical activity by substituting the chemically active groups at the crucial sites of the model fungicide to enhance chemical affinity and introduce conformational changes in the fungicides to make than more effective, active and to some extent cheaper.

Keywords: X-ray crystallography, Systemic fungicides, Triazole structure

Introduction

Recently it has been observed that some of these fungicides are loosing their effects and becoming resistant to them. So that analogous compounds can be designed as substitute, if their structures are known. A rational approach to test these fungicides is to know the three dimensional structure of these compounds and their macromolecular receptor sites as well as their molecular complex. The interactions of proposed fungicides with the macromolecule of the parasite are dependent on the stereochemistry of these compounds. In order to design more effective synthetic fungicides, it is necessary to analyses the three dimensional structure of these compounds and if possible the receptor molecule. The structures of these compounds can be obtained by X-ray diffraction method in crystalline form and they will invariably be similar to their structures in solution.

Experimental

Colorless well formed crystals are grown by slow evaporation technique from a solution of cyclohexanone at 278ºK of both the fungicides. The unit cell parameters are determined by automatic computerized 4-circled Enraf-Nonius CAD-4 Diffractometer. The crystal structure is solved using SHELXS-97. .Bond Lengths of â-4(-Chlorophenoxy)á- (1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol (Angstrom) involving Non-Hydrogen atoms is shown in table 1 and Bond Angles (Degrees) – involving Non-Hydrogen atoms is shown in table2 . Bond Lengths of 1-(4-chlorophenoxy) 3, 3- dimethyl-1-H(1,2,4 triazole-1-Y-1) -2 –butanone (Angstrom) involving Hydrogen atoms is shown in table 3 and Bond Angles (Degrees) – involving Hydrogen atoms is shown in table4. The ORTEP Diagram of 1-(4-chlorophenoxy) 3, 3- dimethyl-1-H(1,2,4 triazole-1-Y-1) -2 –butanone is shown in fig. 1 and the ORTEP Diagram of â-4(-Chlorophenoxy) á-(1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol is shown in fig. 2.

Result and Discussion:

In â-4(-Chlorophenoxy)á- (1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol the average bond distances of C-H and N-H types are 0. 96(2)Å and. 0.90(1)Å respectively. In 1-(4-chlorophenoxy) 3, 3-dimethyl- 1-H(1,2,4 triazole-1-Y-1) -2 –butanone the average bond distance of C-H is 0.95Ú. The bond lengths and angles in the benzene rings show regular features in both the molecules. The C(4)-Cl(1) and Cl(2)-C(18) distances are 1. 748(1)Å and 1. 747(2)Å in â-4(-Chlorophenoxy)á1,1dimethylethyl)1H- 1,2,4-triazole-1-ethano l .The Cl(1A)-C(4A) and Cl (1 B)-C(4B) distances are I .733Ú and 1 .738Ú in 1-(4-chlorophenoxy) 3, 3-dimethyl-1-H(1,2,4 triazole-1-Y-1) -2 –butanone. These distances are short and shortening may be due to delocalization of electrons from the benzene rings. The whole molecules appeared to be twisted and folded and reason may be due to stacking constraints. The bond distances around C(7) and C(21) are as usual shorter than single bond values in â-4(-Chlorophenoxy)-á-1,1dimethylethyl)1H-1,2,4-triazole

Fig. 1: ORTEP Drawing at 50% probability level.

ORTEP Drawing at 50% probability level

Fig. 2: ORTEP DIAGRAM

Ortep Diagram

Table 1: Bond Lengths of â-4(-Chlorophenoxy)á- (1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol (Angstrom) involving Non-Hydrogen atoms.

Cl(1) -C(4) 1.7484(1)
O(1) -C(1) 1.3889(2)
O(1) -C(7) 1.4028(1)
O(2) -C(8) 1.2070(1)
N(1) -N(2) 1.3456(1)
N(1) -C(14) 1.2955(2)
N(2) -C(7) 1.4360(1)
N(2) -C(13) 1.3410(1)
N(3) -C(13) 1.3084(2)
N(3) -C(14) 1.3239(1)
C(1) -C(2) 1.3757(2)
C(1) -C(6) 1.3951(1)
C(2) -C(3) 1.3732(2)
C(3) -C(4) 1.3881(2)
C(4) -C(5) 1.3696(2)
C(5) -C(6) 1.3636(1)
C(7) -C(8) 1.5399(2)
C(8) -C(9) 1.5157(1)
C(9) -C(10) 1.5361(2)
C(9) -C(11) 1.5022(1)
C(9) -C(12) 1.5219(1)
Cl(2) -C(18) 1.7473(2)
O(3) -C(15) 1.3751(1)
O(3) -C(21) 1.4114(2)
O(4) -C(22) 1.1995(2)
N(4) -N(5) 1.3349(1)
N(4) -C(28) 1.3032(1)
N(5) -C(21) 1.4402(2)
N(5) -C(27) 1.3342(1)
N(6) -C(27) 1.3096(2)
N(6) -C(28) 1.2971(1)
C(15) -C(16) 1.3851(1)
C(15) -C(20) 1.3947(2)
C(16) -C(17) 1.3720(2)
C(17) -C(18) 1.3606(1)
C(18) -C(19) 1.3670(2)
C(19) -C(20) 1.3835(1)
C(21) -C(22) 1.5470(2)
C(22) -C(23) 1.5043(2)
C(23) -C(24) 1.5154(2)
C(23) -C(25) 1.4884(1)
C(23) -C(26) 1.5587(1)

Table 2: Bond Angles (Degrees) of â-4(-Chlorophenoxy)á- (1,1dimethylethyl)1H-1,2,4-triazole-1-ethanol (Angles are ordered on the middle label, left to right and top to bottom) involving Non-Hydrogen atoms with estimated standard deviations in parentheses:

C(1) -O(1) -C(7) 119.63(1)
N(2) -N(1) -C(14) 103.80(2)
N(1) -N(2) -C(7) 121.85(2)
N(1) -N(2) -C(13) 107.77(1)
C(7) -N(2) -C(13) 130.36(2)
C(13) -N(3) -C(14) 103.31(1)
O(1) -C(1) -C(2) 125.09(1)
O(1) -C(1) -C(6) 114.80(2)
C(2) -C(1) -C(6) 119.92(1)
C(1) -C(2) -C(3) 120.82(2)
C(2) -C(3) -C(4) 117.98(1)
Cl(1) -C(4) -C(3) 118.81(2)
Cl(1) -C(4) -C(5) 119.23(1)
C(3) -C(4) -C(5) 121.96(1)
C(4) -C(5) -C(6) 119.49(2)
C(1) -C(6) -C(5) 119.74(1)
O(1) -C(7) -N(2) 111.71(2)
O(1) -C(7) -C(8) 100.96(2)
N(2) -C(7) -C(8) 113.64(1)
O(2) -C(8) -C(7) 119.12(1)
O(2) -C(8) -C(9) 123.55(1)
C(7) -C(8) -C(9) 117.34(2)
C(8) -C(9) -C(10) 109.77(1)
C(8) -C(9) -C(11) 109.49(1)
C(8) -C(9) -C(12) 107.05(2)
C(10) -C(9) -C(11) 109.95(1)
C(10) -C(9) -C(12) 109.85(2)
C(11) -C(9) -C(12) 110.69(1)
N(2) -C(13) -N(3) 110.29(1)
N(1) -C(14) -N(3) 114.77(1)
C(15) -O(3) -C(21) 118.87(2)
N(5) -N(4) -C(28) 112.37(1)
N(4) -N(5) -C(21) 130.51(2)
N(4) -N(5) -C(27) 107.91(1)
C(21) -N(5) -C(27) 121.56(1)
C(27) -N(6) -C(28) 118.71(2)
O(3) -C(15) -C(16) 125.05(1)
O(3) -C(15) -C(20) 114.45(2)
C(16) -C(15) -C(20) 120.50(1)
C(15) -C(16) -C(17) 119.72(1)
C(16) -C(17) -C(18) 119.53(2)
Cl(2) -C(18) -C(17) 119.71(2)
Cl(2) -C(18) -C(19) 118.39(1)
C(17) -C(18) -C(19) 121.89(2)
C(18) -C(19) -C(20) 119.78(1)
C(15) -C(20) -C(19) 118.56(2)
O(3) -C(21) -N(5) 111.56(1)
O(3) -C(21) -C(22) 102.56(2)
N(5) -C(21) -C(22) 112.55(1)
O(4) -C(22) -C(21) 119.37(2)
O(4) -C(22) -C(23) 123.16(1)
C(21) -C(22) -C(23) 117.31(2)
C(22) -C(23) -C(24) 112.53(1)
C(22) -C(23) -C(25) 112.27(2)
C(22) -C(23) -C(26) 105.10(1)
C(24) -C(23) -C(25) 112.81(2)
C(24) -C(23) -C(26) 107.22(1)
C(25) -C(23) -C(26) 106.27(2)
N(5) -C(27) -N(6) 100.90(1)
N(4) -C(28) -N(6) 100.06(1)

Table 3: Bond lengths [ A] with estimated standard deviation in parentheses for 1-(4-Chlorophenoxy) 3,3-dimethyl-1- H(1,2,4-triazole-1-Y-1)2-butanone

C1(1A)-C (4A) 1.733 (2)
O (1A) -C (1A) 1.383 (2)
O (1A) -C (7A) 1.423 (2)
O (2A) -C (10A) 1.200 (2)
N (1A) -C (8A) 1.339 (3)
N (1A) -N (2A) 1.361 (2)
N (1A) -C (7A) 1.440 (2)
N (2A) -C (9A) 1.312 (3)
N (3A) -C (8A) 1.315 (3)
N (3A) -C (9A) 1.336 (3)
C (1A) -C (2A) 1.382 (3)
C (1A) -C (6A) 1.386 (3)
C (2A) -C (3A) 1.390 (3)
C (2A) -H (2AA) 0.9300
C (2A) -C (4A) 1.371 (3)
C (3A) -H (3AA) 0.9300
C (3A) -C (5A) 1.381 (3)
C (4A) -C (6A) 1.372 (3)
C (5A) -H (5AA) 0.9300
C (6A) -H (6AA) 0.9300
C (7A) -C (10A) 1.553 (3)
C (7A) -H (7AA) 0.9800
C (8A) -H (6AA) 0.9300
C (9A) -H (8AA) 0.9300
C (10A)-C (11A) 1.512 (3)
C (11A)-C (12A) 1.529 (3)
C (11A)-C (14A) 1.530 (3)
C (11A)-C (13A) 1.542 (3)
C (12A)-H (12A) 0.9600
C (12A)-H (12B) 0.9600
C (12A)-H (12C) 0.9600
C (13A)-H (13A) 0.9600
C (13A)-H (13B) 0.9600
C (13A)-H (13C) 0.9600
C (14A)-H (14A) 0.9600
C (14A)-H (14B) 0.9600
C (14A)-H (14C) 0.9600
C1(1B) -C (4B) 1.738 (2)
C1(1B) -C (1B) 1.388 (2)
O (1B) -C (7B) 1.411 (2)
O (1B) -C (10B) 1.201 (2)
N (1B) -C (9B) 1.337 (3)
N (1B) -N (2B) 1.356 (2)
N (1B) -C (7B) 1.443 (2)
N (2B) -C (8B) 1.316 (3)
N (3B) -C (9B) 1.314 (3)
N (3B) -C (8B) 1.331 (3)
C (1B) -C (2B) 1.381 (3)
C (1B) -C (6B) 1.386 (3)
C (2B) -C (3B) 1.381 (3)

Table 4: Bond angles [degree] with estimated standard deviation in parentheses for 1-(4-Chlorophenoxy) 3,3- dimethyl-1- H(1,2,4-triazole-1-Y-1)2-butanone 1-ethanol.

C (1A) – O (1A) – C (7A) 119.69 (15)
C (8A) – N (1A) – N (2A) 108.92 (18)
C (8A) – N (1A) – C (7A) 130.80 (19)
N (2A) – N (1A) – C (7A) 120.28 (16)
C (9A) – N (1A) – N (1A) 101.36 (19)
C (8A) – N (3A) – C (9A) 101.62 (15)
C (2A) – C (1A) – O (1A) 124.65 (17)
C (2A) – C (1A) – C (6A) 120.37 (19)
O (1A) – C (1A) – C (6A) 114.97 (17)
C (1A) – C (2A) – C (3A) 119.45 (19)
C (1A) – C (2A) – C (2AA) 120.32(16)
C (3A) – C (2A) – C (2AA) 120.34(16)
C (4A) – C (4A) – C (2A) 119.81(12)
C (4A) – C (3A) – C (3AA) 120.12(12)
C (2A) – C (3A) – C (3AA) 120.14(14)
C (3A) – C (4A) – C (5A) 120.62 (12)
C (3A) – C (4A) – C (1A) 120.15 (19)
C (5A) – C (4A) -C (1A) 119.27 (18)
C (6A) – C (5A) -C (4A) 120.14 (12).
C (6A) – C (5A) -H (5AA) 120.02(15)
C (4A) – C (5A)- H (5AA) 120.03(14)
C (5A) – C (6A) – C (1A) 119.72 (12)
C (5A) – C (6A) – H (6AA) 120.14(16)
C (1A) – C (6A) – H (6AA) 120.13(15)
O (1A) -C (7A) – N (1A) 111.06 (16)
O (1A) -C (7A) – C (10A) 101.45 (15)
N (1A) -C (7A) – C (10A) 113.11 (16)
O (1A) -C (7A) – H (7AA) 110.34(18)
N (1A) -C (7A) -H (7AA) 110.32(12)
C (10A) -C (7A) -H (7AA) 110.33(12)
N (3A) – C (8A) -N (1A) 111.24 (12)
N (3A) – C (8A) -H (8AA) 124.42(18)
N (1A) – C (8A) -H (8AA) 124.43(19)
N (2A) – C (9A) -N (3A) 116.66 (12)
N (2A) – C (9A)- H (9AA) 121.54(12)
N (2A) – C (9A) -H (9AA) 121.53(15)
O (2A) – C (10A) -C (11A) 124.62 (12)
O (2A) – C (10A) -C (7A) 118.52 (19)
C (11A) -C (10A) -C (7A) 116.86 (18)
C (10A) -C (11A) -C (12A) 107.47 (18)
C (10A) -C (11A) – C (14A) 109.9 (20)
C (12A) -C (11A) – C (14A) 110.01(20)
C (10A) -C (11A) – C (13A) 110.3 (12)
C (12A) -C (11A) – C (13A) 109..7 (12)
C (14A) -C (11A) – C (13A) 109.4 (12)
C (11A) -C (12A) – H (12A) 109.5(14)
C (11A) -C (112A) H (12B) 109.5(15)
H (12A) – C (12A) – H (12B) 109.5(14)
C (11A) – C (12A) – H (12C) 109.5(12)
H (12A) – C (12A) – H (12C) 109.5(14)
H ( 12B) -C (12A) – H (12C) 109.5(13)
C (11A) – C (13A) – H (13A) 109.5(12)
C (11A) – C (13A) – H (13B) 109.5(11)
H (13A) – C (13A) – H (13B) 109.5(10)
C (11A) – C (13A) – H (13C) 109.5(12)
H ( 13A)- C (13A) – H (13C) 109.5(14)
H ( 13B)- C (13A) – H (13C) 109.5(15)
C (11A) – C (14A) – H (14A) 109.5(14)
C (11A) – C (14A) – H (14B) 109.5(11)
H (14A) – C (14A) – H (14B) 109.5(15)
C (11A) – C (14A) – H (14C) 109.5(14)
H (14A) – C (14A) – H (14C) 109.5(12)
H (14B) – C (14A) – H (14C) 109.5(11)
C (1B) – O (1B) – C (7B) 119.10 (15)
C (9B) – N (1B) – N (2B) 109.03 (17)
C (9B) – N (1B) – C (7B) 130.16 (18)
N (2B) – N (1B) – C (1B) 120.79 (16)
C (8B) – N (2B) – N (8B) 101.42 (18)
C (9B) – N (3B) – C (8B) 101.8 (12)
C (2B) -C (1B) – C (6B) 120.65 (19)
C (2B) -C (1B) -O (1B) 124.74 (17)
C (6B)- C (1B) – O (1B) 114.60 (17)
C (3B)- C (1B) – C (1B) 119.35 (19)
C (3B) -C (2B) – H (2BA) 120.31(14)
C (1B)- C (2B) – H (2BA) 120.34(15)
C (4B)- C (3B) – C (2B) 119.9 (12)
C (4B)- C (3B) – H (3BA) 120.11(16)
C (2B)- C (3B) – H (3BA) 120.12(14)
C (3B)-C (4B) – C (5B) 121.11 (12)
C (3B)-C (4B) – C1(1B) 119.91 (12)
C (3B)- C (4B)- C1 (1B) 119.72 (18)
C (5B)- C (4B)-C (1B) 119.18 (17)
C (4B)- C (5B)- C (6B) 119.5 (12)
C (4B)- C (5B)- H (5BA) 120.22(15)
C (6B)- C (5B)- H (5BA) 120.21(16)
C (5B)- C (6B)- C (1B) 119.52 (12)
C (5B)- C (6B)- H (6BA) 120.25(14)
C (1B)- C (6B)- H (6BA) 120.22(13)
O (1B)- C (7B)- N (1B) 111.33 (16)
O (1B)- C (7B)- C (10B) 101.97 (15)
N (1B)- C (7B)- C (10B) 112.9 (16)
O (1B)- C (7B)- H (10B) 110.12(13)
N (1B) – C (7B)-H (7BA) 110.13(14)
C (10B)-C (7B) -H (7BA) 110.15(12)
N (2B)- C (8B)- N (3B) 116.71 (12)
N (2B)- C (8B)- H (8BA) 121.72(13)
N (3B)- C (8B) -H (8BA) 121.71(13)
N (3B)- C (9B) -N (1B) 111.13 (12)
N ( 3B)-C (9B) H (9BA) 124.54(14)
N (1B) -C (9B) H (9BA) 124.53(16)
O (2B) -C (10B) -C (11B) 123.6 (12)
O (2B) -C (10B) -C (7B) 119.35 (19)
C (11B) – C (10B) -C (7B) 117.01 (18)
C (13B) – C (11B) – C (10B) 110.3 (12)
C (13B) – C (11B) – C (14B) 112.8 (13)
C (10B) – C (11B) – C (14B) 111.5 (12)
C (13B) – C (11B) – C (12B) 107.7 (13)
C (10B) – C (11B) – C (12B) 106.50 (19)
C (14B) – C (11B) – C (12B) 107.8 (12)
C (11B) – C (12B) – H(12D) 109.5(12)
C (11B) – C (12B) – H (12E) 109.5(13)
H (12D) – C (12B) – H (12E) 109.5(14)
C (11B) – C (12B) – H (12F) 109.5(13)
H (12D) – C (12B) -H (12F) 109.5(15)
H (12E) – C (12B) -H (12F) 109.5(13)
C (11B) – C (13B) – H (13D) 109.5(14)
C (11B) – C (13B) – H (13E) 109.5(15)
H (13D) – C (13B)- H (13E) 109.5(14)
C (11B) – C (13B) – H (13F) 109.5(12)
H (13D) – C (13B) – H (13F) 109.5(11)
H (13E) – C (13B) – H (13F) 109.5(11)
C (11B) – C (14B) – H (14D) 109.5(12)
C (11B) – C (14B) – H (14E) 109.5(13)
H (14D) – C (14B)- H (14E) 109.5(13)
C (11B) – C (14B) – H (14F) 109.5(14)
H (14D) – C (14B) – H (14F) 109.5(14)
H (14E) – C (14B) – H (14F) 109.5(14)

The bond distances around C(7A) and C(7B) are usual shorter than single bond values in 1-(4-chlorophenoxy) 3, 3-dimethyl-1-H(1,2,4 triazole-1-Y-1) -2 –butanone. They may also appears to bear a partial double bond character. In â-4(-Chlorophenoxy)á-1,1dimethylethyl-1H-1,2,4-triazole-1 ethanol the C(7)-O(1) and C(21)-O(3) distances are 1. 4028(1)Å and 1. 4114(2)Å respectively. In 1-(4-chlorophenoxy) 3, 3- dimethyl-1-H(1,2,4 triazole-1-Y-1) -2 –butanone. the O(IA) C(7A) and O(2B)-C(7B) distances are 1.423(2) A and 1.411(2). These distances do not change significantly in similar structures, despite variable intermolecular interactions through them. The bond distances in the triazol rings are comparable to corresponding distances is heterocyclic rings 1.339 (A). The average set of data by Spencer is 1.377A and 119° respectively. The dimensions of the methyl groups are normal and comparable with those in 0-methyl obtusaquinone and moscaline hydro bromide.

The molecule is found to adopt a conformation such that the triazolyl ring is inclined angle of 72.9(9)° to the aromatic ring and at an angle of 61. 5(9)° 1 O(1A), C(7A) grouping The resulting arrangement 1ead approach of the ortho-H, H(2A) to the triazol, atoms N(1A) and N (2A) such that both N….H distances lie within the sum of the Vander Walls radii of N and H. There was an accompanying distortion of the exocyclic angles at C(1A) with the C(2A)-C(1A)-O(1A) bond angle of. 124. 65(17)° being considerably larger than the value found for O1(A)-C(IA) C(6A) 114 .97(17)°

The triozolyl ring is planner with C(7A) lying only O.063(7)A from the mean plane. Although the C(8A) and C(9A)-N(3A) distances are somewhat larger than C(8A)-N(3A) and C(9A)-N(2A), in keep With the uncharged canonical valance form. All four C-N distances are shorter than a normal single bond (1.47A). The N(1A)-N(2A) bond is also shorter than a normal single bond (1.45A). The three atoms bonded to N(1) are almost co planer with it. Taken together these data indicate extensive delocalization within the heterocyclic ring. The most note worthy feature of the heterocyclic ring is the asymmetry of the exocyclic angles at N (1A) [ i30.80°1.

We have observed a similar pattern in related triazole systems and it appear to be a function of a triazolyl ring itself rather than the influence of any inter or intramolecular interactions.

The C(1IA), C(1OA), C(7A), O(1A), C(1A) backbone is rather compressed resulting in the main from the orientation of the tert-butyl group, the C(1 1A)- C(1OA)-C(7A)-O(IA) torsion being only 99.17(19)°. From the least square plane equation by Blow’s method, the benzene and triozolyl rings are partially planner since the atomic displacements are much less than their e.s.d’s.The triozolyl ring is inclined to the aromatic ring at an angle of 72.9(9)°

Thus we study the structure of variety of such compounds and correlate their structure with biological activity, so that more safer and effective fungicides at reasonable price can be developed.

Acknowledgement

The Financial assistance provided by Deptt of Science and Technology (D. S. T), New Delhi is gratefully acknowledged.

References

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