Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The thio­phene ring of the title compound, C22H16Cl2N4O2S, is disordered over two positions, corresponding to rotation of approximately 180° about the single C—C bond, with occupancies approximately in a 4:1 ratio. Weak C—H...O hydrogen bonds help in stabilizing the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024701/dn2175sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024701/dn2175Isup2.hkl
Contains datablock I

CCDC reference: 651492

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.131
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.103 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C35 PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 148
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

1,2,4 triazole and 1,2,4 triazole-5-one derivatives have pharmacological properties as antimicrobial (Holla et al., 1998; Ersan et al., 1998; İkizler et al., 1999), anti imflammatory, analgesic, antitumorial, antihypertensive, antiviral activities, coccidiostatic (Tozkoparan et al., 2000; Turan-Zitouni et al.; 1999, Holla et al., 2002). It was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors very useful for preventing breast cancer (Goss et al., 2004, Santen 2003, Clemons et al., 2004). Spectroscopic and crystal structure data of some di-1,2,4-triazole-5-ones have been reported previously (Sancak et al., 2005).

The compound was prepared and first identifed by NMR spectroscopy. In order to confirm the geometry, its X-ray structure determination was carried out. Compound (I) contains four planar rings (Fig. 1), namely two benzene rings [C22—C27 (A) and C33—C38 (B)], a triazole ring (C) and a thiophene ring (D). Deviations from the ideal bond-angle geometry around the Nsp2 atoms of the single bond are observed. The N21—N2—C1 and N1—N3—C31 bond angles are 120.6 (3)° and 120.8 (3)°, respectively, too close to the ideal geometry (120°); however, the N21—N2—C2, C2—N3—C31 and N1—N3—C2 angles [130 (3)°, 124.5 (3)° and 114.1 (3)°, respectively] are distorted. In the triazole ring atom C2 deviate significantly from planarity. We can conclude, that the reason for these two deviation is intramolecular and intermolecular hydrogen bonds with the O21 atom.

The N21C21 bond length [1.269 (4) Å] agree with values reported in the literature [1.261 (4) Å in the 4-amino-3-methtl-1,2,4-triazole- 5-thione derivative of p-nitrobenzaldehyde (Liu et al., 1999), 1.267 (2) Å in 4-(4-hydroxybenzylidenamino)-4H-1,2,4-triazole hemihydrate (Zhu et al., 2000) and 1.271 (3) Å in the 1-acetyl-4- (p-chlorobenzylideneamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one (Çoruh et al., 2003)]. The presence of a substituent on N3 causes a lengthening of the N—N bond length [N1—N3= 1.385 (4) Å] with respect to the corresponding bonds in 5-(2-chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione [N—N= 1.374 (2) Å; Puviarasan et al., 1999] and in 4-methyl-1,2,4- triazole and 1-methyltetrazole [N—N= 1.344 (2) Å; Palmer & Parsons, 1996]. The S—C bond lengths [S11—C12= 1.692 (6) Å and S11—C15= 1.685 (5) Å] agree with value reported in the literature (Vrábel et al., 2005; Yılmaz et al., 2006)].

The thiophene ring is disordered over two positions, corresponding to rotation of approximately 180° about the single C11—C12 bond, with a major-minor ratio of about 78.5:21.5. Such flip-type disorder is rather common in thiophene rings. Weak C—H···O hydrogen bonds may help in stabilizing the crystal structure.

Related literature top

For related literature, see: Clemons et al. (2004); Ersan et al. (1998); Goss & Strasser-Weippl (2004); Holla et al. (1998, 2002); Liu et al. (1999); Palmer & Parsons (1996); Puviarasan et al. (1999); Sancak et al. (2005); Santen (2003); Tozkoparan et al. (2000); Turan-Zitouni, Kaplancikli, Erol & Kilic (1999); Vrábel et al. (2005); Yılmaz, Arslan, Kazak, Sancak & Er (2006); Zhu et al. (2000); Çoruh et al. (2003); İkizler et al. (1999).

Experimental top

3-thiophen-2-yl-methyl-4-aryliden amino-4,5-dihydro-1H-1,2,4-triazole-5-one (0.01 mol)was refluxed with an equivalent amount of natrium in absolute ethanol for 1 h. Then, ethyl bromoacetophenon (0.01 mol) was added and refluxed for an additional 5 h. The precipitate was filtered off, washed with H2O and recrystallized from ethyl alcohol (yield: 72.47%) to give compound 1. m.p.421–422 °K.

IR (KBr) (v, cm-1) 1698 (acetophenon-C=O), 1717 (triazole-C=O), 1584 (–C=N); 1H NMR (DMSO-d6) δ (p.p.m.) 4.27 (s, thiophen-CH2), 5.44 (s, –NCH2), 6.95–7.06 (m, 2H, arH), 7.40–7.73 (m, 4H, arH), 7.81–8.15 (m, 4H, arH), 10.12 (s, –N=CH); 13C NMR (DMSO-d6) δ (p.p.m.) 25.28 (thiophen-CH2), 51.80 (–NCH2), thiophen C:[125.42 (CH), 126.74 (CH), 126.86 (CH), 135.11(C)], ar C: [128.06 (CH), 129.56 (C), 135.11 (C), 136.72(C)], benzene C: [128.20 (CH), 128.83 (CH), 133.93 (C), 134.07 (CH)], 149.89 (triazole-C-5), 144.76 (triazole-C-3), 147.95 (–N=CH), 192.56 (acetophenon-C=O).

Refinement top

The crystal was poor quality. All H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.93 (aromatic) and 0.97 Å (methylene) and with Uiso(H) = 1.2Ueq(C).

Structure description top

1,2,4 triazole and 1,2,4 triazole-5-one derivatives have pharmacological properties as antimicrobial (Holla et al., 1998; Ersan et al., 1998; İkizler et al., 1999), anti imflammatory, analgesic, antitumorial, antihypertensive, antiviral activities, coccidiostatic (Tozkoparan et al., 2000; Turan-Zitouni et al.; 1999, Holla et al., 2002). It was reported that compounds having triazole moieties such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors very useful for preventing breast cancer (Goss et al., 2004, Santen 2003, Clemons et al., 2004). Spectroscopic and crystal structure data of some di-1,2,4-triazole-5-ones have been reported previously (Sancak et al., 2005).

The compound was prepared and first identifed by NMR spectroscopy. In order to confirm the geometry, its X-ray structure determination was carried out. Compound (I) contains four planar rings (Fig. 1), namely two benzene rings [C22—C27 (A) and C33—C38 (B)], a triazole ring (C) and a thiophene ring (D). Deviations from the ideal bond-angle geometry around the Nsp2 atoms of the single bond are observed. The N21—N2—C1 and N1—N3—C31 bond angles are 120.6 (3)° and 120.8 (3)°, respectively, too close to the ideal geometry (120°); however, the N21—N2—C2, C2—N3—C31 and N1—N3—C2 angles [130 (3)°, 124.5 (3)° and 114.1 (3)°, respectively] are distorted. In the triazole ring atom C2 deviate significantly from planarity. We can conclude, that the reason for these two deviation is intramolecular and intermolecular hydrogen bonds with the O21 atom.

The N21C21 bond length [1.269 (4) Å] agree with values reported in the literature [1.261 (4) Å in the 4-amino-3-methtl-1,2,4-triazole- 5-thione derivative of p-nitrobenzaldehyde (Liu et al., 1999), 1.267 (2) Å in 4-(4-hydroxybenzylidenamino)-4H-1,2,4-triazole hemihydrate (Zhu et al., 2000) and 1.271 (3) Å in the 1-acetyl-4- (p-chlorobenzylideneamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one (Çoruh et al., 2003)]. The presence of a substituent on N3 causes a lengthening of the N—N bond length [N1—N3= 1.385 (4) Å] with respect to the corresponding bonds in 5-(2-chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione [N—N= 1.374 (2) Å; Puviarasan et al., 1999] and in 4-methyl-1,2,4- triazole and 1-methyltetrazole [N—N= 1.344 (2) Å; Palmer & Parsons, 1996]. The S—C bond lengths [S11—C12= 1.692 (6) Å and S11—C15= 1.685 (5) Å] agree with value reported in the literature (Vrábel et al., 2005; Yılmaz et al., 2006)].

The thiophene ring is disordered over two positions, corresponding to rotation of approximately 180° about the single C11—C12 bond, with a major-minor ratio of about 78.5:21.5. Such flip-type disorder is rather common in thiophene rings. Weak C—H···O hydrogen bonds may help in stabilizing the crystal structure.

For related literature, see: Clemons et al. (2004); Ersan et al. (1998); Goss & Strasser-Weippl (2004); Holla et al. (1998, 2002); Liu et al. (1999); Palmer & Parsons (1996); Puviarasan et al. (1999); Sancak et al. (2005); Santen (2003); Tozkoparan et al. (2000); Turan-Zitouni, Kaplancikli, Erol & Kilic (1999); Vrábel et al. (2005); Yılmaz, Arslan, Kazak, Sancak & Er (2006); Zhu et al. (2000); Çoruh et al. (2003); İkizler et al. (1999).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. An ORTEP drawing of (I), with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
1-(benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)- 4,5-dihydro-1H-1,2,4-triazol-5-one top
Crystal data top
C22H16Cl2N4O2SF(000) = 1936
Mr = 471.35Dx = 1.461 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1671 reflections
a = 10.9045 (13) Åθ = 1.9–28.0°
b = 18.509 (2) ŵ = 0.43 mm1
c = 21.228 (3) ÅT = 293 K
V = 4284.4 (9) Å3Prism, colourless
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1671 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.103
Graphite monochromatorθmax = 28.0°, θmin = 1.9°
φ and ω scansh = 1414
20905 measured reflectionsk = 2418
5052 independent reflectionsl = 2728
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0469P)2]
where P = (Fo2 + 2Fc2)/3
5052 reflections(Δ/σ)max < 0.001
301 parametersΔρmax = 0.45 e Å3
148 restraintsΔρmin = 0.25 e Å3
Crystal data top
C22H16Cl2N4O2SV = 4284.4 (9) Å3
Mr = 471.35Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.9045 (13) ŵ = 0.43 mm1
b = 18.509 (2) ÅT = 293 K
c = 21.228 (3) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1671 reflections with I > 2σ(I)
20905 measured reflectionsRint = 0.103
5052 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049148 restraints
wR(F2) = 0.131H-atom parameters constrained
S = 0.84Δρmax = 0.45 e Å3
5052 reflectionsΔρmin = 0.25 e Å3
301 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*/UeqOcc. (<1)
Cl211.32634 (11)0.05797 (7)0.56626 (5)0.0926 (4)
Cl221.36468 (11)0.14685 (6)0.39064 (6)0.1026 (5)
O211.0206 (2)0.19915 (13)0.60310 (11)0.0607 (7)
N210.9952 (3)0.12711 (16)0.47299 (13)0.0509 (8)
N20.9344 (2)0.18406 (16)0.50114 (13)0.0480 (7)
N10.7847 (3)0.26329 (17)0.50817 (15)0.0605 (9)
N30.8565 (3)0.26362 (16)0.56198 (14)0.0570 (8)
C211.0907 (3)0.1034 (2)0.50017 (17)0.0525 (10)
H211.11810.12490.53710.063*
C221.1579 (3)0.04203 (19)0.47348 (17)0.0465 (9)
C20.9483 (3)0.2137 (2)0.56163 (18)0.0497 (9)
C261.3275 (4)0.0427 (2)0.4762 (2)0.0662 (11)
H261.39780.05990.49600.079*
C271.2647 (3)0.0163 (2)0.50036 (17)0.0547 (10)
C330.8744 (3)0.4183 (2)0.68112 (18)0.0543 (10)
C10.8337 (3)0.2147 (2)0.47287 (17)0.0533 (10)
C310.8221 (3)0.30610 (19)0.61592 (15)0.0547 (10)
H31A0.82540.27580.65320.066*
H31B0.73800.32210.61070.066*
C320.9029 (3)0.3716 (2)0.62635 (18)0.0531 (10)
O310.9870 (3)0.38367 (15)0.59117 (14)0.0891 (10)
C110.7843 (3)0.1924 (2)0.41043 (16)0.0578 (9)
H11A0.69750.20380.40910.069*
H11B0.79220.14040.40660.069*
C120.8453 (5)0.2270 (3)0.3550 (2)0.0571 (9)0.785 (3)
S110.98134 (13)0.19883 (9)0.32561 (8)0.0713 (6)0.785 (3)
C130.7886 (6)0.2802 (4)0.3212 (3)0.0666 (12)0.785 (3)
H130.71210.30040.32940.080*0.785 (3)
C140.8751 (5)0.3000 (3)0.2677 (3)0.0716 (11)0.785 (3)
H140.85900.33640.23870.086*0.785 (3)
C150.9759 (5)0.2598 (3)0.2667 (3)0.0725 (12)0.785 (3)
H151.03720.26470.23660.087*0.785 (3)
C12'0.8527 (12)0.2212 (7)0.3532 (3)0.0616 (14)*0.215 (3)
S11'0.8163 (7)0.2950 (4)0.3095 (4)0.0722 (14)*0.215 (3)
C13'0.9566 (14)0.1860 (9)0.3320 (8)0.0663 (19)*0.215 (3)
H13'0.99140.14470.34950.080*0.215 (3)
C14'1.0039 (14)0.2273 (9)0.2747 (8)0.0687 (19)*0.215 (3)
H14'1.07340.21370.25220.082*0.215 (3)
C15'0.9356 (11)0.2849 (8)0.2600 (6)0.068 (2)*0.215 (3)
H15'0.95210.31570.22650.081*0.215 (3)
C241.1791 (4)0.0510 (2)0.3943 (2)0.0761 (12)
H241.14990.07390.35830.091*
C380.7842 (4)0.4019 (2)0.72463 (19)0.0665 (11)
H380.73780.36010.71980.080*
C251.2842 (4)0.0750 (2)0.4228 (2)0.0667 (12)
C231.1168 (3)0.0070 (2)0.41901 (19)0.0625 (11)
H231.04600.02320.39920.075*
C370.7628 (5)0.4467 (3)0.7749 (2)0.0892 (14)
H370.70130.43540.80360.107*
C350.9191 (6)0.5250 (3)0.7406 (3)0.1083 (18)
H350.96490.56690.74600.130*
C340.9415 (4)0.4808 (3)0.6892 (2)0.0797 (13)
H341.00170.49320.66010.096*
C360.8312 (6)0.5078 (3)0.7831 (3)0.1050 (18)
H360.81750.53740.81780.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl210.0910 (9)0.1162 (10)0.0705 (8)0.0339 (7)0.0225 (7)0.0168 (7)
Cl220.1150 (10)0.0628 (7)0.1300 (11)0.0048 (7)0.0437 (8)0.0204 (7)
O210.0489 (15)0.0879 (19)0.0453 (16)0.0102 (14)0.0114 (13)0.0059 (14)
N210.046 (2)0.061 (2)0.0453 (19)0.0011 (17)0.0025 (17)0.0016 (16)
N20.0382 (17)0.065 (2)0.040 (2)0.0063 (16)0.0019 (16)0.0020 (16)
N10.056 (2)0.087 (2)0.039 (2)0.0132 (18)0.0074 (17)0.0020 (17)
N30.0498 (19)0.080 (2)0.042 (2)0.0140 (18)0.0010 (16)0.0066 (17)
C210.048 (2)0.063 (3)0.047 (2)0.008 (2)0.001 (2)0.002 (2)
C220.045 (2)0.052 (2)0.043 (2)0.008 (2)0.0049 (19)0.0014 (19)
C20.037 (2)0.068 (3)0.044 (2)0.002 (2)0.0044 (19)0.002 (2)
C260.063 (3)0.059 (3)0.076 (3)0.005 (2)0.013 (2)0.006 (2)
C270.062 (3)0.059 (3)0.044 (2)0.001 (2)0.004 (2)0.002 (2)
C330.048 (2)0.055 (3)0.060 (3)0.009 (2)0.003 (2)0.008 (2)
C10.042 (2)0.073 (3)0.044 (2)0.000 (2)0.002 (2)0.004 (2)
C310.051 (2)0.069 (3)0.044 (2)0.013 (2)0.0054 (18)0.003 (2)
C320.047 (3)0.061 (3)0.052 (3)0.006 (2)0.002 (2)0.011 (2)
O310.081 (2)0.095 (2)0.092 (2)0.0135 (17)0.0432 (19)0.0022 (17)
C110.0467 (19)0.074 (2)0.053 (2)0.0016 (18)0.0051 (16)0.0004 (17)
C120.0515 (17)0.0686 (19)0.0513 (18)0.0075 (16)0.0054 (15)0.0050 (16)
S110.0475 (8)0.1012 (12)0.0653 (10)0.0089 (8)0.0079 (7)0.0066 (9)
C130.064 (2)0.075 (2)0.061 (2)0.013 (2)0.000 (2)0.0037 (19)
C140.077 (2)0.080 (2)0.058 (2)0.014 (2)0.001 (2)0.0063 (19)
C150.069 (2)0.088 (2)0.061 (2)0.018 (2)0.0086 (19)0.004 (2)
C240.083 (3)0.070 (3)0.075 (3)0.018 (3)0.010 (3)0.012 (3)
C380.064 (3)0.073 (3)0.063 (3)0.012 (2)0.006 (2)0.001 (2)
C250.077 (3)0.046 (3)0.077 (3)0.002 (2)0.028 (3)0.005 (2)
C230.058 (3)0.064 (3)0.066 (3)0.006 (2)0.005 (2)0.002 (2)
C370.105 (4)0.093 (4)0.070 (3)0.031 (3)0.016 (3)0.009 (3)
C350.138 (5)0.075 (4)0.112 (5)0.016 (4)0.025 (4)0.022 (4)
C340.069 (3)0.079 (4)0.091 (4)0.010 (3)0.000 (3)0.003 (3)
C360.146 (5)0.085 (4)0.084 (4)0.032 (4)0.004 (4)0.017 (3)
Geometric parameters (Å, º) top
Cl21—C271.733 (4)C12—C131.367 (8)
Cl22—C251.733 (4)C12—S111.692 (6)
O21—C21.212 (4)S11—C151.685 (5)
N21—C211.269 (4)C13—C141.522 (9)
N21—N21.381 (4)C13—H130.9300
N2—C11.374 (4)C14—C151.328 (6)
N2—C21.405 (4)C14—H140.9300
N1—C11.287 (4)C15—H150.9300
N1—N31.385 (4)C12'—C13'1.383 (13)
N3—C21.362 (4)C12'—S11'1.698 (12)
N3—C311.439 (4)S11'—C15'1.682 (10)
C21—C221.465 (5)C13'—C14'1.526 (12)
C21—H210.9300C13'—H13'0.9300
C22—C271.381 (4)C14'—C15'1.337 (11)
C22—C231.399 (5)C14'—H14'0.9300
C26—C251.367 (5)C15'—H15'0.9300
C26—C271.387 (5)C24—C251.370 (5)
C26—H260.9300C24—C231.374 (5)
C33—C341.378 (5)C24—H240.9300
C33—C381.383 (5)C38—C371.372 (5)
C33—C321.482 (5)C38—H380.9300
C1—C111.489 (5)C23—H230.9300
C31—C321.516 (5)C37—C361.366 (6)
C31—H31A0.9700C37—H370.9300
C31—H31B0.9700C35—C361.355 (7)
C32—O311.204 (4)C35—C341.386 (6)
C11—C121.495 (5)C35—H350.9300
C11—C12'1.522 (8)C34—H340.9300
C11—H11A0.9700C36—H360.9300
C11—H11B0.9700
C21—N21—N2117.5 (3)C11—C12—S11123.3 (5)
C1—N2—N21120.6 (3)C15—S11—C1292.1 (3)
C1—N2—C2108.9 (3)C12—C13—C14106.6 (5)
N21—N2—C2130.0 (3)C12—C13—H13126.7
C1—N1—N3104.4 (3)C14—C13—H13126.7
C2—N3—N1114.1 (3)C15—C14—C13112.9 (5)
C2—N3—C31124.5 (3)C15—C14—H14123.5
N1—N3—C31120.8 (3)C13—C14—H14123.5
N21—C21—C22120.2 (3)C14—C15—S11113.1 (4)
N21—C21—H21119.9C14—C15—H15123.4
C22—C21—H21119.9S11—C15—H15123.4
C27—C22—C23116.8 (3)C13'—C12'—C11119.7 (12)
C27—C22—C21121.9 (3)C13'—C12'—S11'113.1 (8)
C23—C22—C21121.2 (4)C11—C12'—S11'127.1 (11)
O21—C2—N3128.7 (4)C15'—S11'—C12'94.1 (6)
O21—C2—N2130.3 (3)C12'—C13'—C14'107.5 (10)
N3—C2—N2101.0 (3)C12'—C13'—H13'126.3
C25—C26—C27118.7 (4)C14'—C13'—H13'126.3
C25—C26—H26120.7C15'—C14'—C13'113.4 (11)
C27—C26—H26120.7C15'—C14'—H14'123.3
C22—C27—C26122.4 (4)C13'—C14'—H14'123.3
C22—C27—Cl21120.5 (3)C14'—C15'—S11'112.0 (9)
C26—C27—Cl21117.1 (3)C14'—C15'—H15'124.0
C34—C33—C38118.7 (4)S11'—C15'—H15'124.0
C34—C33—C32118.4 (4)C25—C24—C23119.9 (4)
C38—C33—C32123.0 (4)C25—C24—H24120.1
N1—C1—N2111.5 (3)C23—C24—H24120.1
N1—C1—C11124.2 (3)C37—C38—C33120.5 (4)
N2—C1—C11124.3 (4)C37—C38—H38119.8
N3—C31—C32113.7 (3)C33—C38—H38119.8
N3—C31—H31A108.8C26—C25—C24120.9 (4)
C32—C31—H31A108.8C26—C25—Cl22119.1 (4)
N3—C31—H31B108.8C24—C25—Cl22119.9 (4)
C32—C31—H31B108.8C24—C23—C22121.3 (4)
H31A—C31—H31B107.7C24—C23—H23119.3
O31—C32—C33122.6 (4)C22—C23—H23119.3
O31—C32—C31120.0 (3)C36—C37—C38120.5 (5)
C33—C32—C31117.4 (3)C36—C37—H37119.8
C1—C11—C12114.9 (3)C38—C37—H37119.8
C1—C11—C12'115.8 (3)C36—C35—C34120.7 (5)
C1—C11—H11A108.6C36—C35—H35119.6
C12—C11—H11A108.6C34—C35—H35119.6
C12'—C11—H11A112.3C33—C34—C35119.9 (5)
C1—C11—H11B108.6C33—C34—H34120.0
C12—C11—H11B108.6C35—C34—H34120.0
C12'—C11—H11B103.7C35—C36—C37119.7 (5)
H11A—C11—H11B107.5C35—C36—H36120.2
C13—C12—C11121.4 (5)C37—C36—H36120.2
C13—C12—S11115.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O210.932.232.916 (4)130
C13—H13···O21i0.932.533.355 (7)148
Symmetry code: (i) x1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC22H16Cl2N4O2S
Mr471.35
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)10.9045 (13), 18.509 (2), 21.228 (3)
V3)4284.4 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.43
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20905, 5052, 1671
Rint0.103
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.131, 0.84
No. of reflections5052
No. of parameters301
No. of restraints148
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.45, 0.25

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21···O210.932.2312.916 (4)130
C13—H13···O21i0.932.5323.355 (7)148
Symmetry code: (i) x1/2, y+1/2, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds