Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023094/bg2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023094/bg2045Isup2.hkl |
CCDC reference: 651478
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.059
- wR factor = 0.184
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level A EXPT005_ALERT_1_A _exptl_crystal_description is missing Crystal habit description. The following tests will not be performed. CRYSR_01
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.89 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 44
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Cansiz et al. (2001); Kane et al. (1988); Reid & Heindel (1976); Sughen & Yoloye (1978); Zhang et al. (1990).
3-aryl-4-amino -5-mercapto-1,2,4-triazole was prepared by the literature method (Zhang et al., 1990; Reid & Heindel, 1976). 2-(4-chlorophenyl)-3-methylbutanoic acid (0.01 mol) and sulfuric chloride (10 ml) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at 75°C for 1.5 h. Then the excessive sulfuric chloride was removed under reduced pressure, and the residue left to cool to room temperature to obtain the 2-(4-chlorophenyl)-3-methylbutanoyl chloride. Then 3-aryl-4-amino-5-mercapto-1,2,4-triazole (0.008 mol) and 20 ml anhydrous acetonitrile were added. The reaction mixture was stirred at refluxed temperature and monitored by TLC. After refluxing for 3 h, the undisolved by-products were removed by filtration immediately and the product (I) precipitated from the filtrate when the solution was cooled to room temperature. It was further purified by recrystallization in ethanol. Crystals suitable for single-crystal X-ray diffraction were obtained by cooling the hot solution of N,N'-dimethylformamide. 1H NMR (DMSO-d6, 400 MHz): 11.30 (s, 1H, NH), 7.92–7.00 (m, 8H, Ph—H), 3.76 (d, 1H, —C—H), 3.00 (s, 1H, S—H), 2.52 (m, 1H, —C—H), 2.35 (s, 3H, Ph—CH3), 1.10 (d, 6H, —CH3); Analysis calculated for C20H21ClN4OS: C 59.91, H 5.28, N 13.97%; found: C 59.97, H 5.25, N 14.00%.
The H atoms were positioned geometrically (C—H = 0.93, 0.96 or 0.98 A ° and N—H = 0.86 A °) and refined using the riding-model approximation, with Uiso(H) = 1.2Ueq(C, N).
Substituted 1,2,4-triazoles have received much attention on account of their important pharmacological activites, such as antiviral, analgesic, antimicrobial, antidepressant and antifungal effect (Sughen & Yoloye, 1978; Cansiz et al.,2001; Kane et al., 1988). Based on the excellent properties of substituted 1,2,4-triazole, we attempted to incorporate 2-(4-chlorophenyl)-3-methylbutanoic acid into the triazole ring system, hoping to find for a novel triazole compound with higher bioactivity. We report here the synthesis and crystal structure of the title compound (I), obtained during this process (Scheme 1).
There are three aromatic rings in the structure, namely a triazole (N1→ N3/C12/C13), a methylbenzene (C14→ C20), and a chlorobenzene (C1→ C6) rings, (Fig 1). The p-methylbenzene and 4-chlorobenzene planes make a dihedral angle of 38.2 (5)°, while the 1,2,4-triazole ring forms dihedral angles of 31.5 (0)° and 68.3 (1)° with the p-methylbenzene and 4-chlorobenzene rings, respectively. Bonds and angles in (I) are unexceptional.
The molecules link to each other into chains through a N—H···O hydrogen bond; in turn, the dimethylformamide solvato molecules are attached to these one-dimensional structures via a second N—H···O interaction (Table 2 and Figures 1 and 2).
For related literature, see: Cansiz et al. (2001); Kane et al. (1988); Reid & Heindel (1976); Sughen & Yoloye (1978); Zhang et al. (1990).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C20H21ClN4OS·C3H7NO | F(000) = 1000 |
Mr = 474.01 | Dx = 1.207 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 846 reflections |
a = 10.235 (4) Å | θ = 2.3–22.5° |
b = 26.654 (12) Å | µ = 0.25 mm−1 |
c = 9.581 (4) Å | T = 298 K |
β = 93.963 (6)° | , colourless |
V = 2607.6 (19) Å3 | 0.30 × 0.15 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5098 independent reflections |
Radiation source: fine-focus sealed tube | 2828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
phi and ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −12→12 |
Tmin = 0.918, Tmax = 0.975 | k = −32→28 |
11679 measured reflections | l = −11→11 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.1043P)2] where P = (Fo2 + 2Fc2)/3 |
5098 reflections | (Δ/σ)max < 0.001 |
292 parameters | Δρmax = 0.35 e Å−3 |
44 restraints | Δρmin = −0.26 e Å−3 |
C20H21ClN4OS·C3H7NO | V = 2607.6 (19) Å3 |
Mr = 474.01 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.235 (4) Å | µ = 0.25 mm−1 |
b = 26.654 (12) Å | T = 298 K |
c = 9.581 (4) Å | 0.30 × 0.15 × 0.10 mm |
β = 93.963 (6)° |
Bruker SMART CCD area-detector diffractometer | 5098 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2828 reflections with I > 2σ(I) |
Tmin = 0.918, Tmax = 0.975 | Rint = 0.043 |
11679 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 44 restraints |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.35 e Å−3 |
5098 reflections | Δρmin = −0.26 e Å−3 |
292 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 | 0.16930 (14) | −0.00080 (4) | 0.83559 (14) | 0.1301 (5) | |
S1 | 0.11276 (10) | 0.38390 (3) | 0.82591 (9) | 0.0871 (3) | |
N1 | 0.4180 (2) | 0.31509 (10) | 1.0000 (3) | 0.0740 (7) | |
N2 | 0.3445 (3) | 0.35624 (10) | 0.9613 (3) | 0.0757 (7) | |
H2B | 0.3685 | 0.3863 | 0.9830 | 0.091* | |
N3 | 0.2390 (2) | 0.29481 (8) | 0.8760 (2) | 0.0573 (6) | |
N4 | 0.1380 (2) | 0.26553 (8) | 0.8176 (2) | 0.0538 (5) | |
H4A | 0.1274 | 0.2620 | 0.7283 | 0.065* | |
O1 | 0.07115 (17) | 0.24620 (7) | 1.02859 (16) | 0.0613 (5) | |
C1 | 0.1062 (3) | 0.06002 (11) | 0.8322 (4) | 0.0793 (9) | |
C2 | 0.0941 (3) | 0.08607 (12) | 0.7078 (3) | 0.0765 (8) | |
H2A | 0.1195 | 0.0715 | 0.6257 | 0.092* | |
C3 | 0.0440 (3) | 0.13405 (11) | 0.7068 (3) | 0.0634 (7) | |
H3A | 0.0361 | 0.1518 | 0.6230 | 0.076* | |
C4 | 0.0052 (2) | 0.15647 (10) | 0.8272 (3) | 0.0532 (6) | |
C5 | 0.0201 (3) | 0.12912 (11) | 0.9516 (3) | 0.0689 (8) | |
H5A | −0.0035 | 0.1437 | 1.0345 | 0.083* | |
C6 | 0.0690 (3) | 0.08105 (12) | 0.9537 (3) | 0.0817 (9) | |
H6A | 0.0767 | 0.0630 | 1.0369 | 0.098* | |
C7 | −0.0459 (2) | 0.21000 (10) | 0.8247 (2) | 0.0516 (6) | |
H7A | −0.0541 | 0.2210 | 0.7269 | 0.062* | |
C8 | −0.1804 (3) | 0.21674 (12) | 0.8848 (3) | 0.0694 (8) | |
H8A | −0.1725 | 0.2071 | 0.9838 | 0.083* | |
C9 | −0.2240 (3) | 0.27065 (14) | 0.8745 (4) | 0.0927 (11) | |
H9A | −0.3071 | 0.2741 | 0.9141 | 0.139* | |
H9B | −0.2321 | 0.2806 | 0.7780 | 0.139* | |
H9C | −0.1605 | 0.2916 | 0.9248 | 0.139* | |
C10 | −0.2807 (3) | 0.18231 (16) | 0.8079 (5) | 0.1045 (13) | |
H10A | −0.3642 | 0.1864 | 0.8465 | 0.157* | |
H10B | −0.2527 | 0.1481 | 0.8186 | 0.157* | |
H10C | −0.2883 | 0.1909 | 0.7104 | 0.157* | |
C11 | 0.0567 (2) | 0.24256 (9) | 0.9014 (2) | 0.0474 (6) | |
C12 | 0.2323 (3) | 0.34601 (11) | 0.8871 (3) | 0.0642 (7) | |
C13 | 0.3519 (2) | 0.27690 (10) | 0.9485 (3) | 0.0580 (7) | |
C14 | 0.3873 (2) | 0.22500 (11) | 0.9720 (3) | 0.0599 (7) | |
C15 | 0.4576 (3) | 0.21229 (13) | 1.0973 (3) | 0.0738 (8) | |
H15A | 0.4821 | 0.2373 | 1.1615 | 0.089* | |
C16 | 0.4902 (3) | 0.16410 (14) | 1.1260 (4) | 0.0909 (10) | |
H16A | 0.5358 | 0.1565 | 1.2107 | 0.109* | |
C17 | 0.4573 (4) | 0.12548 (14) | 1.0319 (5) | 0.0932 (11) | |
C18 | 0.4923 (6) | 0.07157 (18) | 1.0685 (7) | 0.161 (2) | |
H18A | 0.4611 | 0.0500 | 0.9933 | 0.241* | |
H18B | 0.4524 | 0.0622 | 1.1524 | 0.241* | |
H18C | 0.5857 | 0.0684 | 1.0830 | 0.241* | |
C19 | 0.3902 (3) | 0.13830 (13) | 0.9060 (4) | 0.0860 (10) | |
H19A | 0.3682 | 0.1133 | 0.8409 | 0.103* | |
C20 | 0.3556 (3) | 0.18687 (11) | 0.8756 (3) | 0.0684 (8) | |
H20A | 0.3109 | 0.1945 | 0.7905 | 0.082* | |
C21 | 0.5479 (7) | 0.4571 (2) | 0.1282 (8) | 0.166 (2) | |
H21A | 0.5274 | 0.4745 | 0.2080 | 0.199* | |
C22 | 0.7078 (11) | 0.4277 (6) | 0.0050 (10) | 0.317 (6) | |
H22A | 0.6383 | 0.4283 | −0.0676 | 0.476* | |
H22B | 0.7242 | 0.3937 | 0.0344 | 0.476* | |
H22C | 0.7857 | 0.4416 | −0.0298 | 0.476* | |
C23 | 0.7667 (9) | 0.4766 (3) | 0.2044 (15) | 0.319 (6) | |
H23A | 0.7278 | 0.5029 | 0.2562 | 0.479* | |
H23B | 0.8348 | 0.4905 | 0.1521 | 0.479* | |
H23C | 0.8031 | 0.4517 | 0.2681 | 0.479* | |
N5 | 0.6730 (5) | 0.45505 (15) | 0.1142 (6) | 0.1469 (17) | |
O2 | 0.4539 (5) | 0.44186 (13) | 0.0628 (6) | 0.209 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1782 (12) | 0.0764 (7) | 0.1362 (10) | 0.0280 (6) | 0.0133 (8) | 0.0057 (6) |
S1 | 0.1223 (8) | 0.0741 (5) | 0.0620 (5) | 0.0057 (5) | −0.0142 (5) | 0.0044 (4) |
N1 | 0.0710 (15) | 0.0752 (17) | 0.0742 (17) | −0.0165 (13) | −0.0059 (13) | −0.0077 (13) |
N2 | 0.0882 (18) | 0.0666 (16) | 0.0709 (16) | −0.0202 (14) | −0.0050 (14) | −0.0068 (13) |
N3 | 0.0638 (14) | 0.0640 (14) | 0.0435 (12) | −0.0132 (11) | −0.0007 (10) | −0.0030 (10) |
N4 | 0.0629 (13) | 0.0659 (13) | 0.0317 (10) | −0.0124 (10) | −0.0016 (9) | −0.0028 (9) |
O1 | 0.0723 (12) | 0.0795 (12) | 0.0319 (9) | 0.0013 (9) | 0.0020 (8) | −0.0017 (8) |
C1 | 0.091 (2) | 0.0603 (18) | 0.086 (2) | −0.0022 (15) | 0.0001 (18) | −0.0009 (17) |
C2 | 0.091 (2) | 0.076 (2) | 0.064 (2) | −0.0011 (17) | 0.0115 (16) | −0.0098 (16) |
C3 | 0.0729 (18) | 0.0675 (18) | 0.0500 (16) | −0.0069 (14) | 0.0044 (13) | −0.0027 (13) |
C4 | 0.0482 (14) | 0.0645 (16) | 0.0466 (15) | −0.0098 (12) | 0.0015 (11) | 0.0006 (12) |
C5 | 0.083 (2) | 0.0725 (19) | 0.0516 (17) | −0.0048 (15) | 0.0051 (14) | 0.0009 (14) |
C6 | 0.105 (2) | 0.075 (2) | 0.065 (2) | −0.0041 (18) | 0.0004 (17) | 0.0130 (16) |
C7 | 0.0475 (14) | 0.0705 (16) | 0.0365 (13) | −0.0047 (12) | 0.0004 (10) | 0.0020 (11) |
C8 | 0.0513 (16) | 0.100 (2) | 0.0573 (17) | 0.0042 (15) | 0.0107 (13) | 0.0022 (15) |
C9 | 0.067 (2) | 0.114 (3) | 0.097 (3) | 0.0212 (19) | 0.0097 (18) | −0.004 (2) |
C10 | 0.0508 (18) | 0.132 (3) | 0.130 (3) | −0.0175 (19) | 0.007 (2) | −0.009 (2) |
C11 | 0.0509 (14) | 0.0570 (14) | 0.0342 (13) | 0.0073 (11) | 0.0024 (10) | 0.0011 (11) |
C12 | 0.086 (2) | 0.0645 (17) | 0.0422 (14) | −0.0117 (15) | 0.0037 (13) | −0.0023 (12) |
C13 | 0.0538 (15) | 0.0719 (18) | 0.0482 (15) | −0.0135 (14) | 0.0035 (12) | −0.0069 (13) |
C14 | 0.0496 (15) | 0.0718 (18) | 0.0585 (17) | −0.0064 (13) | 0.0051 (12) | −0.0030 (14) |
C15 | 0.0668 (19) | 0.090 (2) | 0.0641 (19) | 0.0027 (16) | −0.0001 (15) | −0.0052 (16) |
C16 | 0.091 (2) | 0.093 (3) | 0.088 (2) | 0.010 (2) | −0.0011 (19) | 0.013 (2) |
C17 | 0.080 (2) | 0.078 (2) | 0.122 (3) | 0.0071 (18) | 0.010 (2) | 0.012 (2) |
C18 | 0.172 (5) | 0.090 (3) | 0.216 (6) | 0.016 (3) | −0.016 (4) | 0.017 (3) |
C19 | 0.0636 (19) | 0.074 (2) | 0.119 (3) | −0.0026 (16) | 0.0008 (19) | −0.017 (2) |
C20 | 0.0490 (15) | 0.077 (2) | 0.079 (2) | −0.0031 (13) | 0.0018 (14) | −0.0107 (16) |
C21 | 0.164 (5) | 0.124 (4) | 0.201 (6) | −0.014 (4) | −0.055 (5) | −0.012 (4) |
C22 | 0.317 (12) | 0.489 (18) | 0.146 (7) | 0.141 (11) | 0.015 (7) | 0.023 (7) |
C23 | 0.211 (7) | 0.139 (5) | 0.576 (17) | −0.011 (5) | −0.202 (10) | −0.043 (8) |
N5 | 0.143 (4) | 0.094 (3) | 0.196 (5) | 0.006 (3) | −0.047 (4) | 0.011 (3) |
O2 | 0.230 (4) | 0.111 (3) | 0.268 (5) | −0.069 (3) | −0.103 (4) | −0.015 (3) |
Cl1—C1 | 1.744 (3) | C9—H9C | 0.9600 |
S1—C12 | 1.662 (3) | C10—H10A | 0.9600 |
N1—C13 | 1.301 (3) | C10—H10B | 0.9600 |
N1—N2 | 1.367 (3) | C10—H10C | 0.9600 |
N2—C12 | 1.336 (4) | C13—C14 | 1.443 (4) |
N2—H2B | 0.8600 | C14—C20 | 1.396 (4) |
N3—C12 | 1.371 (4) | C14—C15 | 1.397 (4) |
N3—N4 | 1.382 (3) | C15—C16 | 1.351 (5) |
N3—C13 | 1.391 (3) | C15—H15A | 0.9300 |
N4—C11 | 1.343 (3) | C16—C17 | 1.394 (5) |
N4—H4A | 0.8600 | C16—H16A | 0.9300 |
O1—C11 | 1.221 (3) | C17—C19 | 1.389 (5) |
C1—C6 | 1.370 (5) | C17—C18 | 1.516 (6) |
C1—C2 | 1.378 (4) | C18—H18A | 0.9600 |
C2—C3 | 1.378 (4) | C18—H18B | 0.9600 |
C2—H2A | 0.9300 | C18—H18C | 0.9600 |
C3—C4 | 1.382 (4) | C19—C20 | 1.368 (4) |
C3—H3A | 0.9300 | C19—H19A | 0.9300 |
C4—C5 | 1.397 (4) | C20—H20A | 0.9300 |
C4—C7 | 1.519 (4) | C21—O2 | 1.183 (7) |
C5—C6 | 1.375 (4) | C21—N5 | 1.298 (7) |
C5—H5A | 0.9300 | C21—H21A | 0.9300 |
C6—H6A | 0.9300 | C22—N5 | 1.343 (10) |
C7—C11 | 1.514 (3) | C22—H22A | 0.9600 |
C7—C8 | 1.539 (4) | C22—H22B | 0.9600 |
C7—H7A | 0.9800 | C22—H22C | 0.9600 |
C8—C9 | 1.506 (5) | C23—N5 | 1.373 (8) |
C8—C10 | 1.528 (5) | C23—H23A | 0.9600 |
C8—H8A | 0.9800 | C23—H23B | 0.9600 |
C9—H9A | 0.9600 | C23—H23C | 0.9600 |
C9—H9B | 0.9600 | ||
C13—N1—N2 | 105.2 (2) | O1—C11—N4 | 121.5 (2) |
C12—N2—N1 | 114.7 (2) | O1—C11—C7 | 124.2 (2) |
C12—N2—H2B | 122.7 | N4—C11—C7 | 114.1 (2) |
N1—N2—H2B | 122.7 | N2—C12—N3 | 101.5 (2) |
C12—N3—N4 | 123.6 (2) | N2—C12—S1 | 130.4 (2) |
C12—N3—C13 | 110.3 (2) | N3—C12—S1 | 128.1 (2) |
N4—N3—C13 | 125.5 (2) | N1—C13—N3 | 108.3 (2) |
C11—N4—N3 | 119.50 (19) | N1—C13—C14 | 124.9 (3) |
C11—N4—H4A | 120.3 | N3—C13—C14 | 126.7 (2) |
N3—N4—H4A | 120.3 | C20—C14—C15 | 118.3 (3) |
C6—C1—C2 | 121.0 (3) | C20—C14—C13 | 123.4 (3) |
C6—C1—Cl1 | 119.3 (3) | C15—C14—C13 | 118.4 (3) |
C2—C1—Cl1 | 119.7 (3) | C16—C15—C14 | 120.7 (3) |
C1—C2—C3 | 119.0 (3) | C16—C15—H15A | 119.6 |
C1—C2—H2A | 120.5 | C14—C15—H15A | 119.6 |
C3—C2—H2A | 120.5 | C15—C16—C17 | 121.7 (4) |
C2—C3—C4 | 121.6 (3) | C15—C16—H16A | 119.2 |
C2—C3—H3A | 119.2 | C17—C16—H16A | 119.2 |
C4—C3—H3A | 119.2 | C19—C17—C16 | 117.6 (3) |
C3—C4—C5 | 117.8 (3) | C19—C17—C18 | 121.9 (4) |
C3—C4—C7 | 120.8 (2) | C16—C17—C18 | 120.5 (4) |
C5—C4—C7 | 121.4 (2) | C17—C18—H18A | 109.5 |
C6—C5—C4 | 121.1 (3) | C17—C18—H18B | 109.5 |
C6—C5—H5A | 119.4 | H18A—C18—H18B | 109.5 |
C4—C5—H5A | 119.4 | C17—C18—H18C | 109.5 |
C1—C6—C5 | 119.4 (3) | H18A—C18—H18C | 109.5 |
C1—C6—H6A | 120.3 | H18B—C18—H18C | 109.5 |
C5—C6—H6A | 120.3 | C20—C19—C17 | 121.5 (3) |
C11—C7—C4 | 107.71 (19) | C20—C19—H19A | 119.2 |
C11—C7—C8 | 111.1 (2) | C17—C19—H19A | 119.2 |
C4—C7—C8 | 114.8 (2) | C19—C20—C14 | 120.2 (3) |
C11—C7—H7A | 107.7 | C19—C20—H20A | 119.9 |
C4—C7—H7A | 107.7 | C14—C20—H20A | 119.9 |
C8—C7—H7A | 107.7 | O2—C21—N5 | 134.6 (8) |
C9—C8—C10 | 110.8 (3) | O2—C21—H21A | 112.7 |
C9—C8—C7 | 110.8 (2) | N5—C21—H21A | 112.7 |
C10—C8—C7 | 109.8 (2) | N5—C22—H22A | 109.5 |
C9—C8—H8A | 108.5 | N5—C22—H22B | 109.5 |
C10—C8—H8A | 108.5 | H22A—C22—H22B | 109.5 |
C7—C8—H8A | 108.5 | N5—C22—H22C | 109.5 |
C8—C9—H9A | 109.5 | H22A—C22—H22C | 109.5 |
C8—C9—H9B | 109.5 | H22B—C22—H22C | 109.5 |
H9A—C9—H9B | 109.5 | N5—C23—H23A | 109.5 |
C8—C9—H9C | 109.5 | N5—C23—H23B | 109.5 |
H9A—C9—H9C | 109.5 | H23A—C23—H23B | 109.5 |
H9B—C9—H9C | 109.5 | N5—C23—H23C | 109.5 |
C8—C10—H10A | 109.5 | H23A—C23—H23C | 109.5 |
C8—C10—H10B | 109.5 | H23B—C23—H23C | 109.5 |
H10A—C10—H10B | 109.5 | C21—N5—C22 | 114.8 (8) |
C8—C10—H10C | 109.5 | C21—N5—C23 | 124.7 (8) |
H10A—C10—H10C | 109.5 | C22—N5—C23 | 120.4 (9) |
H10B—C10—H10C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O2i | 0.86 | 1.86 | 2.694 (4) | 164 |
N4—H4A···O1ii | 0.86 | 1.97 | 2.824 (3) | 170 |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H21ClN4OS·C3H7NO |
Mr | 474.01 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.235 (4), 26.654 (12), 9.581 (4) |
β (°) | 93.963 (6) |
V (Å3) | 2607.6 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.30 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.918, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11679, 5098, 2828 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.184, 0.96 |
No. of reflections | 5098 |
No. of parameters | 292 |
No. of restraints | 44 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.26 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···O2i | 0.86 | 1.86 | 2.694 (4) | 164.1 |
N4—H4A···O1ii | 0.86 | 1.97 | 2.824 (3) | 170.3 |
Symmetry codes: (i) x, y, z+1; (ii) x, −y+1/2, z−1/2. |
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Substituted 1,2,4-triazoles have received much attention on account of their important pharmacological activites, such as antiviral, analgesic, antimicrobial, antidepressant and antifungal effect (Sughen & Yoloye, 1978; Cansiz et al.,2001; Kane et al., 1988). Based on the excellent properties of substituted 1,2,4-triazole, we attempted to incorporate 2-(4-chlorophenyl)-3-methylbutanoic acid into the triazole ring system, hoping to find for a novel triazole compound with higher bioactivity. We report here the synthesis and crystal structure of the title compound (I), obtained during this process (Scheme 1).
There are three aromatic rings in the structure, namely a triazole (N1→ N3/C12/C13), a methylbenzene (C14→ C20), and a chlorobenzene (C1→ C6) rings, (Fig 1). The p-methylbenzene and 4-chlorobenzene planes make a dihedral angle of 38.2 (5)°, while the 1,2,4-triazole ring forms dihedral angles of 31.5 (0)° and 68.3 (1)° with the p-methylbenzene and 4-chlorobenzene rings, respectively. Bonds and angles in (I) are unexceptional.
The molecules link to each other into chains through a N—H···O hydrogen bond; in turn, the dimethylformamide solvato molecules are attached to these one-dimensional structures via a second N—H···O interaction (Table 2 and Figures 1 and 2).