organic compounds
2-{[5-(4-Chlorophenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-(4-nitrophenyl)acetamide
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
The title molecule, C23H18ClN5O4S, is in an `extended' conformation. The central triazole ring makes dihedral angles of 58.14 (6), 86.29 (6) and 41.99 (6)°, respectively, with the adjacent phenyl, chlorophenyl and nitrophenyl rings. In the crystal, molecules are linked via a pair of N—H⋯N hydrogen bonds with an R22(16) ring motif, forming an inversion dimer. The dimers are connected by C—H⋯O hydrogen bonds into a tape structure along [011]. C—H⋯π interactions between the tapes are also observed.
Keywords: crystal structure; phenyltriazole; thiotriazole.
CCDC reference: 1468941
Structure description
1,2,4-Triazole and its derivatives represent one of the most biologically active class of et al., 2015). Others such as Itraconazole, Fluconazole and Posaconazole have been used for the treatment of fungal infection diseases (Godhani et al., 2015). In view of the above facts, we report in this context the synthesis and of the title compound (Fig. 1).
There are a large number of drugs containing a 1,2,4-triazole nucleus in their structures. These include Ribavirin (antiviral), Rizatriptan (antimigraine), Estazolam and Alprazolam (anxiolytic), Letrozole and Anastrozole (breast cancer) (GodhaniIn the crystal, molecules form a tape structure through N—H⋯N and C—H⋯O hydrogen bonds (Table 1 and Fig. 2). C—H⋯π interactions between the tapes contribute to the stabilization of the molecular packing.
Synthesis and crystallization
A suspension of 5-(4-chlorphenoxy)methyl-4-phenyl-1,2,4-triazoline-3-thione (10 mmol), chloro-N-(p-nitrophenyl)acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated until dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 93%; m.p. 207°C. IR (cm−1): 3300 (NH), 1660 (C=O). 1H NMR (CDCl3, p.p.m.): δ 9.2 (s, 1H, NH), 6.7–8.0 (m, 13H, ArH), 4.9 (s, 2H, OCH2), 4.0 (s, 2H,SCH2).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1468941
10.1107/S2414314616004521/is4005sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616004521/is4005Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616004521/is4005Isup3.cml
A suspension of 5-(4-chlorphenoxy)methyl-4-phenyl-1,2,4-triazoline-3-thione (10 mmol), chloro-N-(p-nitrophenyl)acetamide (10 mol) and anhydrous K2CO3 (2.0 g) in dry acetone (50 ml) was heated under reflux with stirring for 3 h. The hot reaction mixture was filtered to remove K2CO3 and the clear filtrate was evaporated until dryness. The solid residue was crystallized from ethanol to give the title compound. Yield: 93%; m.p. 207°C. IR (cm−1): 3300 (NH), 1660 (C=O). 1H NMR (CDCl3, p.p.m.): δ 9.2 (s, 1H, NH), 6.7–8.0 (m, 13H, ArH), 4.9 (s, 2H, OCH2), 4.0 (s, 2H,SCH2).
1,2,4-Triazole and its derivatives represent one of the most biologically active class of
There are a large number of drugs containing a 1,2,4-triazole nucleus in their structures. These include Ribavirin (antiviral), Rizatriptan (antimigraine), Estazolam and Alprazolam (anxiolytic), Letrozole and Anastrozole (breast cancer) (Godhani et al., 2015). Others such as Itraconazole, Fluconazole and Posaconazole have been used for the treatment of fungal infection diseases (Godhani et al., 2015). In view of the above facts, we report in this context the synthesis and of the title compound (Fig. 1).In the crystal, molecules form a tape structure through N—H···N and C—H···O hydrogen bonds (Table 1 and Fig. 2). C—H···π interactions between the tapes contribute to the stabilization of the molecular packing.
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015a).Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme and 50% probability ellipsoids. | |
Fig. 2. A packing diagram of the title compound, showing the tapes formed by N—H···N and C—H···O hydrogen bonds (blue and black dotted lines, respectively). |
C23H18ClN5O4S | Z = 2 |
Mr = 495.93 | F(000) = 512 |
Triclinic, P1 | Dx = 1.494 Mg m−3 |
a = 8.1828 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 12.1541 (3) Å | Cell parameters from 6886 reflections |
c = 12.3654 (3) Å | θ = 4.0–72.3° |
α = 114.474 (1)° | µ = 2.79 mm−1 |
β = 93.681 (1)° | T = 150 K |
γ = 96.949 (1)° | Plate, colourless |
V = 1102.14 (5) Å3 | 0.21 × 0.18 × 0.03 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4084 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 3709 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.023 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.3°, θmin = 4.0° |
ω scans | h = −9→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −14→13 |
Tmin = 0.80, Tmax = 0.93 | l = −15→15 |
8470 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)] = 0.034 | Hydrogen site location: mixed |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.4011P] where P = (Fo2 + 2Fc2)/3 |
4084 reflections | (Δ/σ)max = 0.001 |
307 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C23H18ClN5O4S | γ = 96.949 (1)° |
Mr = 495.93 | V = 1102.14 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1828 (2) Å | Cu Kα radiation |
b = 12.1541 (3) Å | µ = 2.79 mm−1 |
c = 12.3654 (3) Å | T = 150 K |
α = 114.474 (1)° | 0.21 × 0.18 × 0.03 mm |
β = 93.681 (1)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 4084 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | 3709 reflections with I > 2σ(I) |
Tmin = 0.80, Tmax = 0.93 | Rint = 0.023 |
8470 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.17 e Å−3 |
4084 reflections | Δρmin = −0.35 e Å−3 |
307 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 | −0.09452 (6) | 1.08937 (5) | 1.17426 (5) | 0.04449 (14) | |
S1 | 0.85499 (5) | 0.52367 (4) | 0.73580 (3) | 0.02790 (12) | |
O1 | 0.45177 (13) | 0.80389 (9) | 1.06669 (9) | 0.0230 (2) | |
O2 | 0.96933 (13) | 0.31268 (10) | 0.56493 (9) | 0.0260 (2) | |
O3 | 1.30812 (16) | −0.22278 (10) | 0.30629 (10) | 0.0333 (3) | |
O4 | 1.43386 (15) | −0.21478 (10) | 0.46972 (11) | 0.0335 (3) | |
N1 | 0.70644 (15) | 0.61703 (11) | 1.04995 (11) | 0.0215 (3) | |
N2 | 0.82617 (15) | 0.57622 (11) | 0.97273 (11) | 0.0219 (3) | |
N3 | 0.60856 (14) | 0.59829 (11) | 0.87198 (10) | 0.0184 (2) | |
N4 | 1.14142 (15) | 0.27311 (11) | 0.69377 (11) | 0.0215 (3) | |
H4 | 1.1865 | 0.3031 | 0.7717 | 0.026* | |
N5 | 1.34798 (16) | −0.17258 (12) | 0.41598 (12) | 0.0253 (3) | |
C1 | 0.31563 (19) | 0.86299 (14) | 1.08991 (13) | 0.0218 (3) | |
C2 | 0.3516 (2) | 0.98921 (15) | 1.13020 (15) | 0.0289 (3) | |
H2 | 0.4630 | 1.0278 | 1.1399 | 0.035* | |
C3 | 0.2256 (2) | 1.05892 (16) | 1.15629 (16) | 0.0335 (4) | |
H3 | 0.2500 | 1.1454 | 1.1848 | 0.040* | |
C4 | 0.0633 (2) | 1.00125 (16) | 1.14047 (15) | 0.0300 (4) | |
C5 | 0.0266 (2) | 0.87596 (16) | 1.09983 (14) | 0.0281 (3) | |
H5 | −0.0854 | 0.8376 | 1.0887 | 0.034* | |
C6 | 0.15317 (19) | 0.80536 (14) | 1.07504 (13) | 0.0241 (3) | |
H6 | 0.1287 | 0.7191 | 1.0484 | 0.029* | |
C7 | 0.42651 (18) | 0.67518 (13) | 1.03645 (13) | 0.0208 (3) | |
H7A | 0.3285 | 0.6324 | 0.9753 | 0.025* | |
H7B | 0.4086 | 0.6607 | 1.1083 | 0.025* | |
C8 | 0.57961 (18) | 0.63017 (12) | 0.98852 (12) | 0.0189 (3) | |
C9 | 0.76419 (17) | 0.56569 (13) | 0.86746 (13) | 0.0197 (3) | |
C10 | 0.49571 (17) | 0.58946 (13) | 0.77336 (12) | 0.0188 (3) | |
C11 | 0.4338 (2) | 0.69254 (14) | 0.77869 (14) | 0.0255 (3) | |
H11 | 0.4648 | 0.7689 | 0.8467 | 0.031* | |
C12 | 0.3251 (2) | 0.68181 (18) | 0.68222 (15) | 0.0344 (4) | |
H12 | 0.2811 | 0.7514 | 0.6844 | 0.041* | |
C13 | 0.2809 (2) | 0.57079 (19) | 0.58354 (15) | 0.0354 (4) | |
H13 | 0.2066 | 0.5643 | 0.5181 | 0.043* | |
C14 | 0.3442 (2) | 0.46872 (17) | 0.57942 (14) | 0.0299 (4) | |
H14 | 0.3138 | 0.3926 | 0.5109 | 0.036* | |
C15 | 0.45185 (19) | 0.47706 (14) | 0.67500 (13) | 0.0230 (3) | |
H15 | 0.4946 | 0.4071 | 0.6730 | 0.028* | |
C16 | 1.02531 (19) | 0.45839 (14) | 0.77244 (13) | 0.0244 (3) | |
H16A | 1.1299 | 0.5171 | 0.7933 | 0.029* | |
H16B | 1.0057 | 0.4410 | 0.8424 | 0.029* | |
C17 | 1.03937 (17) | 0.34014 (13) | 0.66470 (13) | 0.0203 (3) | |
C18 | 1.18868 (18) | 0.16229 (13) | 0.61799 (13) | 0.0202 (3) | |
C19 | 1.27723 (18) | 0.10494 (14) | 0.67439 (13) | 0.0227 (3) | |
H19 | 1.3019 | 0.1421 | 0.7592 | 0.027* | |
C20 | 1.32914 (19) | −0.00431 (14) | 0.60902 (13) | 0.0237 (3) | |
H20 | 1.3893 | −0.0429 | 0.6477 | 0.028* | |
C21 | 1.29176 (18) | −0.05704 (13) | 0.48524 (13) | 0.0222 (3) | |
C22 | 1.20524 (19) | −0.00199 (14) | 0.42706 (13) | 0.0232 (3) | |
H22 | 1.1816 | −0.0396 | 0.3422 | 0.028* | |
C23 | 1.15320 (19) | 0.10814 (14) | 0.49296 (13) | 0.0231 (3) | |
H23 | 1.0939 | 0.1466 | 0.4537 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0467 (3) | 0.0525 (3) | 0.0530 (3) | 0.0368 (2) | 0.0247 (2) | 0.0304 (2) |
S1 | 0.0279 (2) | 0.0415 (2) | 0.02153 (19) | 0.02142 (17) | 0.00882 (15) | 0.01553 (16) |
O1 | 0.0191 (5) | 0.0182 (5) | 0.0288 (5) | 0.0078 (4) | 0.0043 (4) | 0.0056 (4) |
O2 | 0.0258 (5) | 0.0308 (6) | 0.0187 (5) | 0.0112 (5) | −0.0004 (4) | 0.0067 (4) |
O3 | 0.0445 (7) | 0.0286 (6) | 0.0223 (6) | 0.0105 (5) | 0.0096 (5) | 0.0045 (5) |
O4 | 0.0361 (6) | 0.0279 (6) | 0.0365 (6) | 0.0152 (5) | 0.0051 (5) | 0.0111 (5) |
N1 | 0.0220 (6) | 0.0234 (6) | 0.0170 (6) | 0.0089 (5) | 0.0021 (5) | 0.0053 (5) |
N2 | 0.0206 (6) | 0.0253 (6) | 0.0186 (6) | 0.0098 (5) | 0.0030 (5) | 0.0063 (5) |
N3 | 0.0177 (6) | 0.0205 (6) | 0.0169 (6) | 0.0092 (5) | 0.0023 (5) | 0.0061 (4) |
N4 | 0.0226 (6) | 0.0235 (6) | 0.0160 (6) | 0.0089 (5) | 0.0011 (5) | 0.0049 (5) |
N5 | 0.0260 (7) | 0.0227 (6) | 0.0256 (7) | 0.0058 (5) | 0.0083 (5) | 0.0076 (5) |
C1 | 0.0220 (7) | 0.0243 (7) | 0.0203 (7) | 0.0107 (6) | 0.0047 (6) | 0.0085 (6) |
C2 | 0.0275 (8) | 0.0237 (8) | 0.0349 (8) | 0.0074 (7) | 0.0060 (7) | 0.0108 (6) |
C3 | 0.0397 (9) | 0.0246 (8) | 0.0398 (9) | 0.0144 (7) | 0.0108 (8) | 0.0138 (7) |
C4 | 0.0320 (9) | 0.0357 (9) | 0.0312 (8) | 0.0214 (7) | 0.0122 (7) | 0.0175 (7) |
C5 | 0.0231 (7) | 0.0354 (9) | 0.0291 (8) | 0.0102 (7) | 0.0067 (6) | 0.0151 (7) |
C6 | 0.0238 (7) | 0.0254 (7) | 0.0235 (7) | 0.0086 (6) | 0.0055 (6) | 0.0091 (6) |
C7 | 0.0206 (7) | 0.0190 (7) | 0.0208 (7) | 0.0064 (6) | 0.0038 (6) | 0.0055 (5) |
C8 | 0.0205 (7) | 0.0171 (6) | 0.0173 (6) | 0.0058 (6) | 0.0025 (5) | 0.0048 (5) |
C9 | 0.0177 (7) | 0.0201 (7) | 0.0202 (7) | 0.0077 (6) | 0.0023 (5) | 0.0064 (5) |
C10 | 0.0164 (6) | 0.0244 (7) | 0.0174 (7) | 0.0074 (6) | 0.0021 (5) | 0.0095 (5) |
C11 | 0.0296 (8) | 0.0262 (8) | 0.0250 (7) | 0.0129 (6) | 0.0065 (6) | 0.0125 (6) |
C12 | 0.0390 (9) | 0.0474 (10) | 0.0313 (9) | 0.0273 (8) | 0.0115 (8) | 0.0246 (8) |
C13 | 0.0283 (8) | 0.0634 (12) | 0.0216 (8) | 0.0206 (8) | 0.0050 (7) | 0.0211 (8) |
C14 | 0.0237 (7) | 0.0418 (9) | 0.0187 (7) | 0.0062 (7) | 0.0020 (6) | 0.0073 (6) |
C15 | 0.0220 (7) | 0.0252 (7) | 0.0205 (7) | 0.0077 (6) | 0.0037 (6) | 0.0074 (6) |
C16 | 0.0206 (7) | 0.0287 (8) | 0.0201 (7) | 0.0113 (6) | 0.0014 (6) | 0.0049 (6) |
C17 | 0.0164 (6) | 0.0237 (7) | 0.0198 (7) | 0.0055 (6) | 0.0037 (5) | 0.0076 (6) |
C18 | 0.0174 (6) | 0.0219 (7) | 0.0199 (7) | 0.0059 (6) | 0.0037 (5) | 0.0066 (6) |
C19 | 0.0228 (7) | 0.0260 (7) | 0.0176 (7) | 0.0063 (6) | 0.0020 (6) | 0.0072 (6) |
C20 | 0.0234 (7) | 0.0258 (7) | 0.0237 (7) | 0.0082 (6) | 0.0029 (6) | 0.0113 (6) |
C21 | 0.0213 (7) | 0.0210 (7) | 0.0222 (7) | 0.0058 (6) | 0.0068 (6) | 0.0061 (6) |
C22 | 0.0243 (7) | 0.0254 (7) | 0.0172 (7) | 0.0048 (6) | 0.0028 (6) | 0.0062 (6) |
C23 | 0.0241 (7) | 0.0261 (8) | 0.0189 (7) | 0.0081 (6) | 0.0019 (6) | 0.0084 (6) |
Cl1—C4 | 1.7387 (16) | C7—C8 | 1.487 (2) |
S1—C9 | 1.7383 (15) | C7—H7A | 0.9900 |
S1—C16 | 1.8061 (15) | C7—H7B | 0.9900 |
O1—C1 | 1.3796 (18) | C10—C11 | 1.386 (2) |
O1—C7 | 1.4343 (18) | C10—C15 | 1.387 (2) |
O2—C17 | 1.2181 (18) | C11—C12 | 1.392 (2) |
O3—N5 | 1.2360 (17) | C11—H11 | 0.9500 |
O4—N5 | 1.2281 (18) | C12—C13 | 1.379 (3) |
N1—C8 | 1.3111 (19) | C12—H12 | 0.9500 |
N1—N2 | 1.4010 (18) | C13—C14 | 1.384 (3) |
N2—C9 | 1.3151 (18) | C13—H13 | 0.9500 |
N3—C8 | 1.3734 (19) | C14—C15 | 1.389 (2) |
N3—C9 | 1.3765 (18) | C14—H14 | 0.9500 |
N3—C10 | 1.4403 (17) | C15—H15 | 0.9500 |
N4—C17 | 1.3634 (19) | C16—C17 | 1.525 (2) |
N4—C18 | 1.4031 (18) | C16—H16A | 0.9900 |
N4—H4 | 0.9098 | C16—H16B | 0.9900 |
N5—C21 | 1.4586 (19) | C18—C19 | 1.399 (2) |
C1—C2 | 1.388 (2) | C18—C23 | 1.400 (2) |
C1—C6 | 1.389 (2) | C19—C20 | 1.374 (2) |
C2—C3 | 1.383 (2) | C19—H19 | 0.9500 |
C2—H2 | 0.9500 | C20—C21 | 1.388 (2) |
C3—C4 | 1.386 (3) | C20—H20 | 0.9500 |
C3—H3 | 0.9500 | C21—C22 | 1.384 (2) |
C4—C5 | 1.377 (2) | C22—C23 | 1.384 (2) |
C5—C6 | 1.393 (2) | C22—H22 | 0.9500 |
C5—H5 | 0.9500 | C23—H23 | 0.9500 |
C6—H6 | 0.9500 | ||
C9—S1—C16 | 100.00 (7) | C11—C10—N3 | 119.63 (13) |
C1—O1—C7 | 117.68 (12) | C15—C10—N3 | 118.71 (13) |
C8—N1—N2 | 107.77 (12) | C10—C11—C12 | 118.59 (15) |
C9—N2—N1 | 106.62 (11) | C10—C11—H11 | 120.7 |
C8—N3—C9 | 104.71 (11) | C12—C11—H11 | 120.7 |
C8—N3—C10 | 127.83 (12) | C13—C12—C11 | 120.44 (15) |
C9—N3—C10 | 127.22 (12) | C13—C12—H12 | 119.8 |
C17—N4—C18 | 128.21 (12) | C11—C12—H12 | 119.8 |
C17—N4—H4 | 117.2 | C12—C13—C14 | 120.28 (15) |
C18—N4—H4 | 114.6 | C12—C13—H13 | 119.9 |
O4—N5—O3 | 123.20 (13) | C14—C13—H13 | 119.9 |
O4—N5—C21 | 118.18 (13) | C13—C14—C15 | 120.28 (15) |
O3—N5—C21 | 118.62 (13) | C13—C14—H14 | 119.9 |
O1—C1—C2 | 114.63 (14) | C15—C14—H14 | 119.9 |
O1—C1—C6 | 124.88 (14) | C10—C15—C14 | 118.74 (15) |
C2—C1—C6 | 120.50 (14) | C10—C15—H15 | 120.6 |
C3—C2—C1 | 120.19 (16) | C14—C15—H15 | 120.6 |
C3—C2—H2 | 119.9 | C17—C16—S1 | 109.03 (10) |
C1—C2—H2 | 119.9 | C17—C16—H16A | 109.9 |
C2—C3—C4 | 119.29 (16) | S1—C16—H16A | 109.9 |
C2—C3—H3 | 120.4 | C17—C16—H16B | 109.9 |
C4—C3—H3 | 120.4 | S1—C16—H16B | 109.9 |
C5—C4—C3 | 120.85 (15) | H16A—C16—H16B | 108.3 |
C5—C4—Cl1 | 120.03 (14) | O2—C17—N4 | 125.33 (13) |
C3—C4—Cl1 | 119.12 (13) | O2—C17—C16 | 122.69 (13) |
C4—C5—C6 | 120.16 (15) | N4—C17—C16 | 111.96 (12) |
C4—C5—H5 | 119.9 | C19—C18—C23 | 119.61 (13) |
C6—C5—H5 | 119.9 | C19—C18—N4 | 116.02 (13) |
C1—C6—C5 | 119.00 (15) | C23—C18—N4 | 124.37 (13) |
C1—C6—H6 | 120.5 | C20—C19—C18 | 121.02 (13) |
C5—C6—H6 | 120.5 | C20—C19—H19 | 119.5 |
O1—C7—C8 | 106.20 (12) | C18—C19—H19 | 119.5 |
O1—C7—H7A | 110.5 | C19—C20—C21 | 118.54 (14) |
C8—C7—H7A | 110.5 | C19—C20—H20 | 120.7 |
O1—C7—H7B | 110.5 | C21—C20—H20 | 120.7 |
C8—C7—H7B | 110.5 | C22—C21—C20 | 121.67 (14) |
H7A—C7—H7B | 108.7 | C22—C21—N5 | 119.88 (13) |
N1—C8—N3 | 110.23 (13) | C20—C21—N5 | 118.45 (13) |
N1—C8—C7 | 125.83 (13) | C21—C22—C23 | 119.76 (14) |
N3—C8—C7 | 123.93 (12) | C21—C22—H22 | 120.1 |
N2—C9—N3 | 110.67 (13) | C23—C22—H22 | 120.1 |
N2—C9—S1 | 128.89 (11) | C22—C23—C18 | 119.40 (13) |
N3—C9—S1 | 120.39 (10) | C22—C23—H23 | 120.3 |
C11—C10—C15 | 121.66 (13) | C18—C23—H23 | 120.3 |
C8—N1—N2—C9 | −0.55 (16) | C8—N3—C10—C15 | −118.65 (16) |
C7—O1—C1—C2 | 173.83 (13) | C9—N3—C10—C15 | 54.9 (2) |
C7—O1—C1—C6 | −6.6 (2) | C15—C10—C11—C12 | −0.1 (2) |
O1—C1—C2—C3 | 179.81 (15) | N3—C10—C11—C12 | 179.91 (14) |
C6—C1—C2—C3 | 0.2 (2) | C10—C11—C12—C13 | −0.2 (3) |
C1—C2—C3—C4 | −0.7 (3) | C11—C12—C13—C14 | 0.0 (3) |
C2—C3—C4—C5 | 0.3 (3) | C12—C13—C14—C15 | 0.5 (3) |
C2—C3—C4—Cl1 | 179.61 (13) | C11—C10—C15—C14 | 0.6 (2) |
C3—C4—C5—C6 | 0.6 (3) | N3—C10—C15—C14 | −179.44 (13) |
Cl1—C4—C5—C6 | −178.67 (12) | C13—C14—C15—C10 | −0.7 (2) |
O1—C1—C6—C5 | −178.85 (14) | C9—S1—C16—C17 | 136.78 (11) |
C2—C1—C6—C5 | 0.7 (2) | C18—N4—C17—O2 | 0.8 (3) |
C4—C5—C6—C1 | −1.1 (2) | C18—N4—C17—C16 | −177.53 (14) |
C1—O1—C7—C8 | 166.87 (12) | S1—C16—C17—O2 | 14.43 (19) |
N2—N1—C8—N3 | 0.69 (16) | S1—C16—C17—N4 | −167.17 (11) |
N2—N1—C8—C7 | −178.20 (13) | C17—N4—C18—C19 | −171.74 (14) |
C9—N3—C8—N1 | −0.55 (16) | C17—N4—C18—C23 | 8.4 (2) |
C10—N3—C8—N1 | 174.12 (13) | C23—C18—C19—C20 | −0.4 (2) |
C9—N3—C8—C7 | 178.37 (13) | N4—C18—C19—C20 | 179.69 (14) |
C10—N3—C8—C7 | −7.0 (2) | C18—C19—C20—C21 | 0.0 (2) |
O1—C7—C8—N1 | 95.45 (17) | C19—C20—C21—C22 | 0.4 (2) |
O1—C7—C8—N3 | −83.30 (16) | C19—C20—C21—N5 | 179.58 (14) |
N1—N2—C9—N3 | 0.21 (16) | O4—N5—C21—C22 | 175.23 (14) |
N1—N2—C9—S1 | 177.76 (11) | O3—N5—C21—C22 | −4.3 (2) |
C8—N3—C9—N2 | 0.19 (16) | O4—N5—C21—C20 | −3.9 (2) |
C10—N3—C9—N2 | −174.52 (13) | O3—N5—C21—C20 | 176.57 (14) |
C8—N3—C9—S1 | −177.60 (10) | C20—C21—C22—C23 | −0.3 (2) |
C10—N3—C9—S1 | 7.7 (2) | N5—C21—C22—C23 | −179.48 (14) |
C16—S1—C9—N2 | 15.55 (16) | C21—C22—C23—C18 | −0.1 (2) |
C16—S1—C9—N3 | −167.10 (12) | C19—C18—C23—C22 | 0.5 (2) |
C8—N3—C10—C11 | 61.4 (2) | N4—C18—C23—C22 | −179.62 (14) |
C9—N3—C10—C11 | −125.12 (16) |
Cg1, Cg2 and Cg3 are the centroids of the 1,2,4-triazole (N1/N2/C9/N3/C8), benzene (C1–C6) and phenyl (C10–C15) rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N1i | 0.91 | 2.08 | 2.9934 (17) | 176 |
C15—H15···O4ii | 0.95 | 2.44 | 3.2324 (19) | 140 |
C5—H5···Cg1iii | 0.95 | 2.97 | 3.757 (2) | 141 |
C16—H16A···Cg3iv | 0.99 | 2.82 | 3.6284 (18) | 139 |
C22—H22···Cg2v | 0.95 | 2.69 | 3.5883 (16) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x+1, y−1, z−1. |
Cg1, Cg2 and Cg3 are the centroids of the 1,2,4-triazole (N1/N2/C9/N3/C8), benzene (C1–C6) and phenyl (C10–C15) rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N1i | 0.91 | 2.08 | 2.9934 (17) | 176 |
C15—H15···O4ii | 0.95 | 2.44 | 3.2324 (19) | 140 |
C5—H5···Cg1iii | 0.95 | 2.97 | 3.757 (2) | 141 |
C16—H16A···Cg3iv | 0.99 | 2.82 | 3.6284 (18) | 139 |
C22—H22···Cg2v | 0.95 | 2.69 | 3.5883 (16) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) x+1, y−1, z−1. |
Experimental details
Crystal data | |
Chemical formula | C23H18ClN5O4S |
Mr | 495.93 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 8.1828 (2), 12.1541 (3), 12.3654 (3) |
α, β, γ (°) | 114.474 (1), 93.681 (1), 96.949 (1) |
V (Å3) | 1102.14 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.79 |
Crystal size (mm) | 0.21 × 0.18 × 0.03 |
Data collection | |
Diffractometer | Bruker D8 VENTURE PHOTON 100 CMOS |
Absorption correction | Multi-scan (SADABS; Bruker, 2016) |
Tmin, Tmax | 0.80, 0.93 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8470, 4084, 3709 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.089, 1.04 |
No. of reflections | 4084 |
No. of parameters | 307 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.35 |
Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015b), SHELXL2014 (Sheldrick, 2015a), DIAMOND (Brandenburg & Putz, 2012).
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
References
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, WI. Google Scholar
Godhani, D. R., Jogel, A. A., Sanghani, A. M. & Mehta, J. P. (2015). Indian J. Chem. Section B, 54, 556–564. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
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