1-(Benzoyl­meth­yl)-4-[(2,4-dichloro­benzyl­idene)amino]-3-(2-thienylmeth­yl)-4,5-dihydro-1H-1,2,4-triazol-5-one

Ustabaş, R.; Çoruh, U.; Sancak, K.; Ünver, Y.; Vázquez-López, E.M.

doi:10.1107/S1600536807024701

Buy article online - an online subscription or single-article purchase is required to access this article.

1-(Benzoylmethyl)-4-[(2,4-dichlorobenzylidene)amino]-3-(2-thienylmethyl)-4,5-dihydro-1H-1,2,4-triazol-5-one

R. Ustabaş, U. Çoruh, K. Sancak, Y. Ünver and E. M. Vázquez-López

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024701/dn2175sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024701/dn2175Isup2.hkl Contains datablock I

CCDC reference: 651492

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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 N21═C21 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).

Structure description top

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

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

C₂₂H₁₆Cl₂N₄O₂S	F(000) = 1936
M_r = 471.35	D_x = 1.461 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1671 reflections
a = 10.9045 (13) Å	θ = 1.9–28.0°
b = 18.509 (2) Å	µ = 0.43 mm⁻¹
c = 21.228 (3) Å	T = 293 K
V = 4284.4 (9) Å³	Prism, colourless
Z = 8	0.30 × 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 tube	R_int = 0.103
Graphite monochromator	θ_max = 28.0°, θ_min = 1.9°
φ and ω scans	h = −14→14
20905 measured reflections	k = −24→18
5052 independent reflections	l = −27→28

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 0.84	w = 1/[σ²(F_o²) + (0.0469P)²] where P = (F_o² + 2F_c²)/3
5052 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.45 e Å⁻³
148 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₁₆Cl₂N₄O₂S	V = 4284.4 (9) Å³
M_r = 471.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.9045 (13) Å	µ = 0.43 mm⁻¹
b = 18.509 (2) Å	T = 293 K
c = 21.228 (3) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1671 reflections with I > 2σ(I)
20905 measured reflections	R_int = 0.103
5052 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	148 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 0.84	Δρ_max = 0.45 e Å⁻³
5052 reflections	Δρ_min = −0.25 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl21	1.32634 (11)	0.05797 (7)	0.56626 (5)	0.0926 (4)
Cl22	1.36468 (11)	−0.14685 (6)	0.39064 (6)	0.1026 (5)
O21	1.0206 (2)	0.19915 (13)	0.60310 (11)	0.0607 (7)
N21	0.9952 (3)	0.12711 (16)	0.47299 (13)	0.0509 (8)
N2	0.9344 (2)	0.18406 (16)	0.50114 (13)	0.0480 (7)
N1	0.7847 (3)	0.26329 (17)	0.50817 (15)	0.0605 (9)
N3	0.8565 (3)	0.26362 (16)	0.56198 (14)	0.0570 (8)
C21	1.0907 (3)	0.1034 (2)	0.50017 (17)	0.0525 (10)
H21	1.1181	0.1249	0.5371	0.063*
C22	1.1579 (3)	0.04203 (19)	0.47348 (17)	0.0465 (9)
C2	0.9483 (3)	0.2137 (2)	0.56163 (18)	0.0497 (9)
C26	1.3275 (4)	−0.0427 (2)	0.4762 (2)	0.0662 (11)
H26	1.3978	−0.0599	0.4960	0.079*
C27	1.2647 (3)	0.0163 (2)	0.50036 (17)	0.0547 (10)
C33	0.8744 (3)	0.4183 (2)	0.68112 (18)	0.0543 (10)
C1	0.8337 (3)	0.2147 (2)	0.47287 (17)	0.0533 (10)
C31	0.8221 (3)	0.30610 (19)	0.61592 (15)	0.0547 (10)
H31A	0.8254	0.2758	0.6532	0.066*
H31B	0.7380	0.3221	0.6107	0.066*
C32	0.9029 (3)	0.3716 (2)	0.62635 (18)	0.0531 (10)
O31	0.9870 (3)	0.38367 (15)	0.59117 (14)	0.0891 (10)
C11	0.7843 (3)	0.1924 (2)	0.41043 (16)	0.0578 (9)
H11A	0.6975	0.2038	0.4091	0.069*
H11B	0.7922	0.1404	0.4066	0.069*
C12	0.8453 (5)	0.2270 (3)	0.3550 (2)	0.0571 (9)	0.785 (3)
S11	0.98134 (13)	0.19883 (9)	0.32561 (8)	0.0713 (6)	0.785 (3)
C13	0.7886 (6)	0.2802 (4)	0.3212 (3)	0.0666 (12)	0.785 (3)
H13	0.7121	0.3004	0.3294	0.080*	0.785 (3)
C14	0.8751 (5)	0.3000 (3)	0.2677 (3)	0.0716 (11)	0.785 (3)
H14	0.8590	0.3364	0.2387	0.086*	0.785 (3)
C15	0.9759 (5)	0.2598 (3)	0.2667 (3)	0.0725 (12)	0.785 (3)
H15	1.0372	0.2647	0.2366	0.087*	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'	0.9914	0.1447	0.3495	0.080*	0.215 (3)
C14'	1.0039 (14)	0.2273 (9)	0.2747 (8)	0.0687 (19)*	0.215 (3)
H14'	1.0734	0.2137	0.2522	0.082*	0.215 (3)
C15'	0.9356 (11)	0.2849 (8)	0.2600 (6)	0.068 (2)*	0.215 (3)
H15'	0.9521	0.3157	0.2265	0.081*	0.215 (3)
C24	1.1791 (4)	−0.0510 (2)	0.3943 (2)	0.0761 (12)
H24	1.1499	−0.0739	0.3583	0.091*
C38	0.7842 (4)	0.4019 (2)	0.72463 (19)	0.0665 (11)
H38	0.7378	0.3601	0.7198	0.080*
C25	1.2842 (4)	−0.0750 (2)	0.4228 (2)	0.0667 (12)
C23	1.1168 (3)	0.0070 (2)	0.41901 (19)	0.0625 (11)
H23	1.0460	0.0232	0.3992	0.075*
C37	0.7628 (5)	0.4467 (3)	0.7749 (2)	0.0892 (14)
H37	0.7013	0.4354	0.8036	0.107*
C35	0.9191 (6)	0.5250 (3)	0.7406 (3)	0.1083 (18)
H35	0.9649	0.5669	0.7460	0.130*
C34	0.9415 (4)	0.4808 (3)	0.6892 (2)	0.0797 (13)
H34	1.0017	0.4932	0.6601	0.096*
C36	0.8312 (6)	0.5078 (3)	0.7831 (3)	0.1050 (18)
H36	0.8175	0.5374	0.8178	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl21	0.0910 (9)	0.1162 (10)	0.0705 (8)	0.0339 (7)	−0.0225 (7)	−0.0168 (7)
Cl22	0.1150 (10)	0.0628 (7)	0.1300 (11)	0.0048 (7)	0.0437 (8)	−0.0204 (7)
O21	0.0489 (15)	0.0879 (19)	0.0453 (16)	0.0102 (14)	−0.0114 (13)	−0.0059 (14)
N21	0.046 (2)	0.061 (2)	0.0453 (19)	−0.0011 (17)	−0.0025 (17)	−0.0016 (16)
N2	0.0382 (17)	0.065 (2)	0.040 (2)	0.0063 (16)	−0.0019 (16)	−0.0020 (16)
N1	0.056 (2)	0.087 (2)	0.039 (2)	0.0132 (18)	−0.0074 (17)	0.0020 (17)
N3	0.0498 (19)	0.080 (2)	0.042 (2)	0.0140 (18)	0.0010 (16)	−0.0066 (17)
C21	0.048 (2)	0.063 (3)	0.047 (2)	−0.008 (2)	0.001 (2)	−0.002 (2)
C22	0.045 (2)	0.052 (2)	0.043 (2)	−0.008 (2)	0.0049 (19)	0.0014 (19)
C2	0.037 (2)	0.068 (3)	0.044 (2)	0.002 (2)	0.0044 (19)	0.002 (2)
C26	0.063 (3)	0.059 (3)	0.076 (3)	0.005 (2)	0.013 (2)	0.006 (2)
C27	0.062 (3)	0.059 (3)	0.044 (2)	−0.001 (2)	0.004 (2)	0.002 (2)
C33	0.048 (2)	0.055 (3)	0.060 (3)	0.009 (2)	−0.003 (2)	0.008 (2)
C1	0.042 (2)	0.073 (3)	0.044 (2)	0.000 (2)	0.002 (2)	0.004 (2)
C31	0.051 (2)	0.069 (3)	0.044 (2)	0.013 (2)	0.0054 (18)	0.003 (2)
C32	0.047 (3)	0.061 (3)	0.052 (3)	0.006 (2)	0.002 (2)	0.011 (2)
O31	0.081 (2)	0.095 (2)	0.092 (2)	−0.0135 (17)	0.0432 (19)	0.0022 (17)
C11	0.0467 (19)	0.074 (2)	0.053 (2)	−0.0016 (18)	−0.0051 (16)	0.0004 (17)
C12	0.0515 (17)	0.0686 (19)	0.0513 (18)	−0.0075 (16)	−0.0054 (15)	−0.0050 (16)
S11	0.0475 (8)	0.1012 (12)	0.0653 (10)	−0.0089 (8)	0.0079 (7)	−0.0066 (9)
C13	0.064 (2)	0.075 (2)	0.061 (2)	−0.013 (2)	0.000 (2)	0.0037 (19)
C14	0.077 (2)	0.080 (2)	0.058 (2)	−0.014 (2)	−0.001 (2)	0.0063 (19)
C15	0.069 (2)	0.088 (2)	0.061 (2)	−0.018 (2)	0.0086 (19)	−0.004 (2)
C24	0.083 (3)	0.070 (3)	0.075 (3)	−0.018 (3)	0.010 (3)	−0.012 (3)
C38	0.064 (3)	0.073 (3)	0.063 (3)	0.012 (2)	0.006 (2)	0.001 (2)
C25	0.077 (3)	0.046 (3)	0.077 (3)	−0.002 (2)	0.028 (3)	−0.005 (2)
C23	0.058 (3)	0.064 (3)	0.066 (3)	−0.006 (2)	0.005 (2)	−0.002 (2)
C37	0.105 (4)	0.093 (4)	0.070 (3)	0.031 (3)	0.016 (3)	−0.009 (3)
C35	0.138 (5)	0.075 (4)	0.112 (5)	−0.016 (4)	−0.025 (4)	−0.022 (4)
C34	0.069 (3)	0.079 (4)	0.091 (4)	−0.010 (3)	0.000 (3)	0.003 (3)
C36	0.146 (5)	0.085 (4)	0.084 (4)	0.032 (4)	−0.004 (4)	−0.017 (3)

Geometric parameters (Å, º) top

Cl21—C27	1.733 (4)	C12—C13	1.367 (8)
Cl22—C25	1.733 (4)	C12—S11	1.692 (6)
O21—C2	1.212 (4)	S11—C15	1.685 (5)
N21—C21	1.269 (4)	C13—C14	1.522 (9)
N21—N2	1.381 (4)	C13—H13	0.9300
N2—C1	1.374 (4)	C14—C15	1.328 (6)
N2—C2	1.405 (4)	C14—H14	0.9300
N1—C1	1.287 (4)	C15—H15	0.9300
N1—N3	1.385 (4)	C12'—C13'	1.383 (13)
N3—C2	1.362 (4)	C12'—S11'	1.698 (12)
N3—C31	1.439 (4)	S11'—C15'	1.682 (10)
C21—C22	1.465 (5)	C13'—C14'	1.526 (12)
C21—H21	0.9300	C13'—H13'	0.9300
C22—C27	1.381 (4)	C14'—C15'	1.337 (11)
C22—C23	1.399 (5)	C14'—H14'	0.9300
C26—C25	1.367 (5)	C15'—H15'	0.9300
C26—C27	1.387 (5)	C24—C25	1.370 (5)
C26—H26	0.9300	C24—C23	1.374 (5)
C33—C34	1.378 (5)	C24—H24	0.9300
C33—C38	1.383 (5)	C38—C37	1.372 (5)
C33—C32	1.482 (5)	C38—H38	0.9300
C1—C11	1.489 (5)	C23—H23	0.9300
C31—C32	1.516 (5)	C37—C36	1.366 (6)
C31—H31A	0.9700	C37—H37	0.9300
C31—H31B	0.9700	C35—C36	1.355 (7)
C32—O31	1.204 (4)	C35—C34	1.386 (6)
C11—C12	1.495 (5)	C35—H35	0.9300
C11—C12'	1.522 (8)	C34—H34	0.9300
C11—H11A	0.9700	C36—H36	0.9300
C11—H11B	0.9700

C21—N21—N2	117.5 (3)	C11—C12—S11	123.3 (5)
C1—N2—N21	120.6 (3)	C15—S11—C12	92.1 (3)
C1—N2—C2	108.9 (3)	C12—C13—C14	106.6 (5)
N21—N2—C2	130.0 (3)	C12—C13—H13	126.7
C1—N1—N3	104.4 (3)	C14—C13—H13	126.7
C2—N3—N1	114.1 (3)	C15—C14—C13	112.9 (5)
C2—N3—C31	124.5 (3)	C15—C14—H14	123.5
N1—N3—C31	120.8 (3)	C13—C14—H14	123.5
N21—C21—C22	120.2 (3)	C14—C15—S11	113.1 (4)
N21—C21—H21	119.9	C14—C15—H15	123.4
C22—C21—H21	119.9	S11—C15—H15	123.4
C27—C22—C23	116.8 (3)	C13'—C12'—C11	119.7 (12)
C27—C22—C21	121.9 (3)	C13'—C12'—S11'	113.1 (8)
C23—C22—C21	121.2 (4)	C11—C12'—S11'	127.1 (11)
O21—C2—N3	128.7 (4)	C15'—S11'—C12'	94.1 (6)
O21—C2—N2	130.3 (3)	C12'—C13'—C14'	107.5 (10)
N3—C2—N2	101.0 (3)	C12'—C13'—H13'	126.3
C25—C26—C27	118.7 (4)	C14'—C13'—H13'	126.3
C25—C26—H26	120.7	C15'—C14'—C13'	113.4 (11)
C27—C26—H26	120.7	C15'—C14'—H14'	123.3
C22—C27—C26	122.4 (4)	C13'—C14'—H14'	123.3
C22—C27—Cl21	120.5 (3)	C14'—C15'—S11'	112.0 (9)
C26—C27—Cl21	117.1 (3)	C14'—C15'—H15'	124.0
C34—C33—C38	118.7 (4)	S11'—C15'—H15'	124.0
C34—C33—C32	118.4 (4)	C25—C24—C23	119.9 (4)
C38—C33—C32	123.0 (4)	C25—C24—H24	120.1
N1—C1—N2	111.5 (3)	C23—C24—H24	120.1
N1—C1—C11	124.2 (3)	C37—C38—C33	120.5 (4)
N2—C1—C11	124.3 (4)	C37—C38—H38	119.8
N3—C31—C32	113.7 (3)	C33—C38—H38	119.8
N3—C31—H31A	108.8	C26—C25—C24	120.9 (4)
C32—C31—H31A	108.8	C26—C25—Cl22	119.1 (4)
N3—C31—H31B	108.8	C24—C25—Cl22	119.9 (4)
C32—C31—H31B	108.8	C24—C23—C22	121.3 (4)
H31A—C31—H31B	107.7	C24—C23—H23	119.3
O31—C32—C33	122.6 (4)	C22—C23—H23	119.3
O31—C32—C31	120.0 (3)	C36—C37—C38	120.5 (5)
C33—C32—C31	117.4 (3)	C36—C37—H37	119.8
C1—C11—C12	114.9 (3)	C38—C37—H37	119.8
C1—C11—C12'	115.8 (3)	C36—C35—C34	120.7 (5)
C1—C11—H11A	108.6	C36—C35—H35	119.6
C12—C11—H11A	108.6	C34—C35—H35	119.6
C12'—C11—H11A	112.3	C33—C34—C35	119.9 (5)
C1—C11—H11B	108.6	C33—C34—H34	120.0
C12—C11—H11B	108.6	C35—C34—H34	120.0
C12'—C11—H11B	103.7	C35—C36—C37	119.7 (5)
H11A—C11—H11B	107.5	C35—C36—H36	120.2
C13—C12—C11	121.4 (5)	C37—C36—H36	120.2
C13—C12—S11	115.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O21	0.93	2.23	2.916 (4)	130
C13—H13···O21ⁱ	0.93	2.53	3.355 (7)	148

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆Cl₂N₄O₂S
M_r	471.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	10.9045 (13), 18.509 (2), 21.228 (3)
V (Å³)	4284.4 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20905, 5052, 1671
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.131, 0.84
No. of reflections	5052
No. of parameters	301
No. of restraints	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C21—H21···O21	0.93	2.231	2.916 (4)	130
C13—H13···O21ⁱ	0.93	2.532	3.355 (7)	148

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

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

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page