7-(4-Chloro­benzyl­idene)-3-[(4-chloro­phen­oxy)meth­yl]-6-(4-nitro­thio­phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

Fun, H.-K.; Asik, S.I.J.; Razak, I.A.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811015637

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1266-o1267

doi:10.1107/S1600536811015637

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7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

Hoong-Kun Fun,^a ^*‡ Safra Izuani Jama Asik,^a Ibrahim Abdul Razak,^a Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 21 April 2011; accepted 26 April 2011; online 29 April 2011)

In the title compound, C₂₂H₁₃Cl₂N₅O₃S₂, the thiadiazine ring adopts a half-chair conformation. The benzene rings of the chlorophenoxy and chlorobenzyl groups and the thiophene ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the triazole ring. In the crystal, molecules are connected into sheets parallel to ( $[\overline{1}]$ 11) by intermolecular C—H⋯N and C—H⋯Cl hydrogen bonds. In addition, π–π stacking interactions are observed between thiophene and triazole rings, and between inversion-related triazole rings [centroid–centroid distances = 3.5975 (11) and 3.4324 (11) Å].

Related literature

For general background to and applications of 1,2,4-triazole derivatives, see: Shujuan et al. (2004 ); Clemons et al. (2004 ); Johnston (2002 ); Wei et al. (2007 ). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ); Jin et al. (2004 ). For related structures, see: Goh et al. (2010a ,b ,c ,d ).

Experimental

Crystal data

C₂₂H₁₃Cl₂N₅O₃S₂
M_r = 530.39
Triclinic, $[P \overline 1]$
a = 8.5021 (2) Å
b = 10.0379 (2) Å
c = 14.3623 (3) Å
α = 94.434 (1)°
β = 97.981 (1)°
γ = 109.242 (1)°
V = 1136.07 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 296 K
0.39 × 0.32 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.827, T_max = 0.946
19590 measured reflections
6548 independent reflections
5142 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.133
S = 1.04
6548 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N2ⁱ	0.93	2.60	3.495 (3)	162
C21—H21A⋯Cl1ⁱⁱ	0.93	2.81	3.691 (2)	159
Symmetry codes: (i) x+1, y+1, z; (ii) x, y-1, z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015637/ci5185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015637/ci5185Isup2.hkl

checkCIF report

Comment top

The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting compounds. Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), while vorozole, letrozole and anastrozole are non-steroidal drugs used for the treatment of cancer (Clemons et al., 2004) and loreclezole is used as an anticonvulsant (Johnston et al., 2002). Similarly substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). In continuation of our search on the synthesis of biologically active compounds, we synthesized triazolothiadiazine from triazole.

In the title compound, the 1,2,4-triazole (C8/N1–N3/C9) and thiophene (C12–C15/S2) rings are essentially planar, with maximum deviations of 0.006 (2) and 0.003 (2) Å for atom C9 and C14, respectively. The 1,3,4-thiadiazine (C9–C11/N3/N4/S1) ring is slightly distorted and may be regarded as having a half-chair conformation with puckering parameters, Q = 0.474 (2) Å, θ = 113.9 (2)°, ϕ = 149.1 (2)° (Cremer & Pople, 1975).

The two benzene rings (C1–C6 and C17–C22) and the thiophene (C12–C15/S2) ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the 1,2,4-triazole ring (C8/N1–N3/C9). The geometric parameters are consistent with those observed in closely related structures (Goh et al., 2010a,b,c,d). The bond lengths show normal values (Allen et al. 1987).

In the crystal packing (Fig. 2), the molecules are connected by intermolecular C15—H15A···N2 and C21—H21A···Cl1 interactions that link the molecules into two–dimensional arrays parallel to the (1 1 1). In addition, the molecular packing is also stabilized by π–π stacking interactions between thiophene (C12–C15/S2; centroid Cg1) and 1,2,4-triazole (C8/N1–N3/C9; centroid Cg2) rings, with a Cg1···Cg2^# separation of 3.5975 (11) Å (symmetry code #: 1-x, 1-y, -z), and that between 1,2,4-triazole (C8/N1–N3/C9) rings at (x, y, z) and (-x, 1-y, -z), with their centroids separated by 3.4324 (11) Å.

Related literature top

For general background and applications of 1,2,4-triazole derivatives, see: Shujuan et al. (2004); Clemons et al. (2004); Johnston (2002); Wei et al. (2007). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987); Jin et al. (2004). For related structures, see: Goh et al. (2010a,b,c,d).

Experimental top

To a soultion of 4-Amino-5-[(p-chlorophenoxy)methyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 2-bromo-3-(p-chlorophenyl)-1-(5-nitrothiophen-2-yl) prop-2-en-1-one (0.01 mol) in ethanol, a catalytic amount of anhydrous sodium acetate was added. The solution was refluxed on a water bath for 9 h. The solid product that separated out was filtered and dried. It was then recrystallized from ethanol. Single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)- 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine top

Crystal data top

C₂₂H₁₃Cl₂N₅O₃S₂	Z = 2
M_r = 530.39	F(000) = 540
Triclinic, P1	D_x = 1.551 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5021 (2) Å	Cell parameters from 5767 reflections
b = 10.0379 (2) Å	θ = 2.7–32.0°
c = 14.3623 (3) Å	µ = 0.51 mm⁻¹
α = 94.434 (1)°	T = 296 K
β = 97.981 (1)°	Plate, yellow
γ = 109.242 (1)°	0.39 × 0.32 × 0.11 mm
V = 1136.07 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6548 independent reflections
Radiation source: fine-focus sealed tube	5142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.827, T_max = 0.946	k = −14→14
19590 measured reflections	l = −20→20

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0647P)² + 0.3979P] where P = (F_o² + 2F_c²)/3
6548 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₂₂H₁₃Cl₂N₅O₃S₂	γ = 109.242 (1)°
M_r = 530.39	V = 1136.07 (4) Å³
Triclinic, P1	Z = 2
a = 8.5021 (2) Å	Mo Kα radiation
b = 10.0379 (2) Å	µ = 0.51 mm⁻¹
c = 14.3623 (3) Å	T = 296 K
α = 94.434 (1)°	0.39 × 0.32 × 0.11 mm
β = 97.981 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6548 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5142 reflections with I > 2σ(I)
T_min = 0.827, T_max = 0.946	R_int = 0.031
19590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
6548 reflections	Δρ_min = −0.46 e Å⁻³
307 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.31310 (6)	0.39243 (5)	0.13806 (3)	0.03764 (12)
S2	0.65367 (7)	0.90408 (5)	0.02701 (4)	0.04462 (14)
Cl1	0.32206 (12)	1.05741 (9)	−0.46034 (7)	0.0906 (3)
Cl2	0.17004 (8)	0.36669 (8)	0.58962 (4)	0.06035 (17)
N1	0.0052 (2)	0.34827 (18)	−0.09684 (11)	0.0418 (4)
N2	0.0543 (2)	0.29741 (17)	−0.01333 (11)	0.0391 (3)
N3	0.23458 (18)	0.51207 (16)	−0.01635 (10)	0.0316 (3)
N4	0.37735 (19)	0.63329 (16)	0.00403 (10)	0.0349 (3)
N5	1.0471 (2)	0.9832 (2)	0.22741 (17)	0.0602 (5)
O1	0.25195 (18)	0.62527 (17)	−0.20276 (10)	0.0451 (3)
O2	1.1570 (3)	1.0856 (3)	0.2079 (2)	0.0994 (8)
O3	1.0661 (3)	0.9215 (3)	0.29489 (15)	0.0825 (6)
C1	0.1175 (3)	0.7481 (2)	−0.31056 (13)	0.0416 (4)
H1A	0.0097	0.6926	−0.3027	0.050*
C2	0.1376 (3)	0.8504 (2)	−0.37127 (14)	0.0455 (5)
H2A	0.0436	0.8644	−0.4045	0.055*
C3	0.2982 (3)	0.9316 (2)	−0.38211 (16)	0.0486 (5)
C4	0.4404 (3)	0.9153 (3)	−0.33232 (18)	0.0540 (5)
H4A	0.5479	0.9717	−0.3399	0.065*
C5	0.4199 (3)	0.8139 (2)	−0.27120 (15)	0.0464 (5)
H5A	0.5145	0.8028	−0.2364	0.056*
C6	0.2593 (2)	0.7284 (2)	−0.26134 (12)	0.0367 (4)
C7	0.0975 (3)	0.5693 (2)	−0.16998 (14)	0.0433 (4)
H7A	0.0089	0.5158	−0.2227	0.052*
H7B	0.0664	0.6464	−0.1426	0.052*
C8	0.1140 (2)	0.4746 (2)	−0.09737 (12)	0.0355 (4)
C9	0.1912 (2)	0.39706 (18)	0.03185 (12)	0.0321 (3)
C10	0.4010 (2)	0.57962 (18)	0.16945 (12)	0.0314 (3)
C11	0.4557 (2)	0.66196 (18)	0.09118 (12)	0.0317 (3)
C12	0.6138 (2)	0.78458 (19)	0.10904 (12)	0.0336 (3)
C13	0.7497 (2)	0.8140 (2)	0.17988 (13)	0.0379 (4)
H13A	0.7535	0.7623	0.2307	0.045*
C14	0.8840 (2)	0.9339 (2)	0.16526 (15)	0.0416 (4)
C15	0.8518 (3)	0.9942 (2)	0.08699 (16)	0.0456 (5)
H15A	0.9278	1.0739	0.0687	0.055*
C16	0.4132 (2)	0.64263 (19)	0.25710 (12)	0.0351 (4)
H16A	0.4627	0.7413	0.2673	0.042*
C17	0.3573 (2)	0.57331 (19)	0.33897 (12)	0.0336 (3)
C18	0.2834 (3)	0.6385 (2)	0.40089 (13)	0.0405 (4)
H18A	0.2732	0.7258	0.3906	0.049*
C19	0.2251 (3)	0.5746 (2)	0.47743 (13)	0.0435 (4)
H19A	0.1746	0.6180	0.5179	0.052*
C20	0.2426 (2)	0.4462 (2)	0.49313 (12)	0.0392 (4)
C21	0.3189 (3)	0.3808 (2)	0.43452 (13)	0.0411 (4)
H21A	0.3314	0.2947	0.4463	0.049*
C22	0.3765 (2)	0.4453 (2)	0.35809 (12)	0.0377 (4)
H22A	0.4290	0.4021	0.3188	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0452 (3)	0.0336 (2)	0.0311 (2)	0.01036 (19)	0.00304 (18)	0.00748 (16)
S2	0.0439 (3)	0.0399 (3)	0.0487 (3)	0.0095 (2)	0.0095 (2)	0.0183 (2)
Cl1	0.1026 (6)	0.0671 (4)	0.1053 (6)	0.0239 (4)	0.0179 (5)	0.0532 (4)
Cl2	0.0592 (4)	0.0895 (4)	0.0412 (3)	0.0276 (3)	0.0205 (2)	0.0311 (3)
N1	0.0374 (9)	0.0467 (9)	0.0348 (8)	0.0072 (7)	0.0040 (6)	0.0042 (7)
N2	0.0395 (9)	0.0373 (8)	0.0343 (8)	0.0054 (7)	0.0059 (6)	0.0041 (6)
N3	0.0280 (7)	0.0361 (7)	0.0276 (6)	0.0057 (6)	0.0063 (5)	0.0072 (5)
N4	0.0309 (7)	0.0381 (8)	0.0310 (7)	0.0043 (6)	0.0068 (6)	0.0083 (6)
N5	0.0348 (10)	0.0588 (12)	0.0699 (14)	0.0003 (9)	0.0002 (9)	−0.0045 (10)
O1	0.0376 (7)	0.0657 (9)	0.0394 (7)	0.0221 (7)	0.0121 (6)	0.0219 (6)
O2	0.0397 (10)	0.0808 (15)	0.144 (2)	−0.0193 (10)	−0.0013 (12)	0.0271 (14)
O3	0.0505 (11)	0.1096 (17)	0.0642 (12)	0.0057 (11)	−0.0134 (9)	0.0150 (11)
C1	0.0357 (10)	0.0531 (11)	0.0356 (9)	0.0142 (9)	0.0050 (7)	0.0100 (8)
C2	0.0512 (12)	0.0492 (11)	0.0379 (10)	0.0227 (10)	0.0005 (8)	0.0052 (8)
C3	0.0614 (14)	0.0369 (10)	0.0472 (11)	0.0146 (9)	0.0109 (10)	0.0109 (8)
C4	0.0462 (12)	0.0482 (12)	0.0640 (14)	0.0089 (10)	0.0117 (10)	0.0162 (10)
C5	0.0370 (10)	0.0531 (12)	0.0483 (11)	0.0151 (9)	0.0045 (8)	0.0099 (9)
C6	0.0361 (9)	0.0473 (10)	0.0274 (8)	0.0153 (8)	0.0051 (7)	0.0060 (7)
C7	0.0338 (10)	0.0613 (12)	0.0345 (9)	0.0139 (9)	0.0063 (7)	0.0156 (8)
C8	0.0308 (9)	0.0439 (10)	0.0287 (8)	0.0090 (7)	0.0048 (6)	0.0046 (7)
C9	0.0328 (8)	0.0338 (8)	0.0285 (7)	0.0086 (7)	0.0076 (6)	0.0050 (6)
C10	0.0283 (8)	0.0348 (8)	0.0291 (8)	0.0071 (7)	0.0062 (6)	0.0073 (6)
C11	0.0302 (8)	0.0349 (8)	0.0295 (8)	0.0083 (7)	0.0086 (6)	0.0075 (6)
C12	0.0316 (9)	0.0332 (8)	0.0328 (8)	0.0049 (7)	0.0087 (7)	0.0074 (6)
C13	0.0331 (9)	0.0427 (10)	0.0329 (8)	0.0063 (8)	0.0058 (7)	0.0053 (7)
C14	0.0309 (9)	0.0404 (10)	0.0457 (10)	0.0031 (8)	0.0069 (8)	0.0002 (8)
C15	0.0408 (11)	0.0304 (9)	0.0591 (12)	0.0004 (8)	0.0172 (9)	0.0059 (8)
C16	0.0346 (9)	0.0352 (9)	0.0315 (8)	0.0056 (7)	0.0082 (7)	0.0046 (7)
C17	0.0302 (8)	0.0395 (9)	0.0274 (8)	0.0073 (7)	0.0052 (6)	0.0037 (6)
C18	0.0448 (11)	0.0387 (9)	0.0372 (9)	0.0115 (8)	0.0118 (8)	0.0053 (7)
C19	0.0466 (11)	0.0532 (12)	0.0327 (9)	0.0178 (9)	0.0138 (8)	0.0031 (8)
C20	0.0331 (9)	0.0540 (11)	0.0263 (8)	0.0086 (8)	0.0047 (7)	0.0089 (7)
C21	0.0434 (11)	0.0495 (11)	0.0341 (9)	0.0201 (9)	0.0051 (8)	0.0118 (8)
C22	0.0389 (10)	0.0496 (10)	0.0278 (8)	0.0192 (8)	0.0060 (7)	0.0055 (7)

Geometric parameters (Å, º) top

S1—C9	1.7342 (18)	C5—C6	1.386 (3)
S1—C10	1.7727 (18)	C5—H5A	0.93
S2—C15	1.694 (2)	C7—C8	1.486 (3)
S2—C12	1.7330 (17)	C7—H7A	0.97
Cl1—C3	1.736 (2)	C7—H7B	0.97
Cl2—C20	1.7386 (18)	C10—C16	1.339 (2)
N1—C8	1.302 (2)	C10—C11	1.483 (2)
N1—N2	1.403 (2)	C11—C12	1.467 (2)
N2—C9	1.303 (2)	C12—C13	1.364 (3)
N3—C9	1.364 (2)	C13—C14	1.413 (3)
N3—C8	1.376 (2)	C13—H13A	0.93
N3—N4	1.383 (2)	C14—C15	1.354 (3)
N4—C11	1.296 (2)	C15—H15A	0.93
N5—O3	1.210 (3)	C16—C17	1.468 (2)
N5—O2	1.221 (3)	C16—H16A	0.93
N5—C14	1.449 (3)	C17—C22	1.391 (3)
O1—C6	1.375 (2)	C17—C18	1.397 (3)
O1—C7	1.410 (2)	C18—C19	1.384 (3)
C1—C2	1.382 (3)	C18—H18A	0.93
C1—C6	1.391 (3)	C19—C20	1.377 (3)
C1—H1A	0.93	C19—H19A	0.93
C2—C3	1.378 (3)	C20—C21	1.381 (3)
C2—H2A	0.93	C21—C22	1.383 (3)
C3—C4	1.381 (3)	C21—H21A	0.93
C4—C5	1.378 (3)	C22—H22A	0.93
C4—H4A	0.93

C9—S1—C10	95.62 (8)	N3—C9—S1	121.40 (13)
C15—S2—C12	92.18 (10)	C16—C10—C11	122.26 (16)
C8—N1—N2	107.87 (15)	C16—C10—S1	122.39 (13)
C9—N2—N1	106.29 (15)	C11—C10—S1	115.32 (12)
C9—N3—C8	104.63 (14)	N4—C11—C12	114.57 (15)
C9—N3—N4	128.75 (14)	N4—C11—C10	125.55 (16)
C8—N3—N4	126.23 (14)	C12—C11—C10	119.85 (15)
C11—N4—N3	115.80 (14)	C13—C12—C11	128.47 (16)
O3—N5—O2	124.2 (2)	C13—C12—S2	111.57 (14)
O3—N5—C14	118.5 (2)	C11—C12—S2	119.62 (13)
O2—N5—C14	117.2 (2)	C12—C13—C14	110.48 (17)
C6—O1—C7	115.44 (15)	C12—C13—H13A	124.8
C2—C1—C6	119.61 (19)	C14—C13—H13A	124.8
C2—C1—H1A	120.2	C15—C14—C13	115.29 (18)
C6—C1—H1A	120.2	C15—C14—N5	122.83 (19)
C3—C2—C1	119.4 (2)	C13—C14—N5	121.8 (2)
C3—C2—H2A	120.3	C14—C15—S2	110.47 (15)
C1—C2—H2A	120.3	C14—C15—H15A	124.8
C2—C3—C4	121.7 (2)	S2—C15—H15A	124.8
C2—C3—Cl1	119.05 (18)	C10—C16—C17	127.24 (17)
C4—C3—Cl1	119.29 (18)	C10—C16—H16A	116.4
C5—C4—C3	118.8 (2)	C17—C16—H16A	116.4
C5—C4—H4A	120.6	C22—C17—C18	118.34 (16)
C3—C4—H4A	120.6	C22—C17—C16	122.56 (16)
C4—C5—C6	120.4 (2)	C18—C17—C16	119.10 (17)
C4—C5—H5A	119.8	C19—C18—C17	120.80 (18)
C6—C5—H5A	119.8	C19—C18—H18A	119.6
O1—C6—C5	116.08 (17)	C17—C18—H18A	119.6
O1—C6—C1	123.84 (17)	C20—C19—C18	119.36 (18)
C5—C6—C1	120.07 (18)	C20—C19—H19A	120.3
O1—C7—C8	109.98 (16)	C18—C19—H19A	120.3
O1—C7—H7A	109.7	C19—C20—C21	121.20 (17)
C8—C7—H7A	109.7	C19—C20—Cl2	119.24 (15)
O1—C7—H7B	109.7	C21—C20—Cl2	119.55 (16)
C8—C7—H7B	109.7	C20—C21—C22	119.05 (18)
H7A—C7—H7B	108.2	C20—C21—H21A	120.5
N1—C8—N3	109.93 (16)	C22—C21—H21A	120.5
N1—C8—C7	124.21 (17)	C21—C22—C17	121.21 (17)
N3—C8—C7	125.52 (17)	C21—C22—H22A	119.4
N2—C9—N3	111.26 (15)	C17—C22—H22A	119.4
N2—C9—S1	127.32 (14)

C8—N1—N2—C9	−0.1 (2)	C16—C10—C11—N4	−140.1 (2)
C9—N3—N4—C11	−21.5 (3)	S1—C10—C11—N4	38.2 (2)
C8—N3—N4—C11	166.81 (17)	C16—C10—C11—C12	42.0 (3)
C6—C1—C2—C3	0.0 (3)	S1—C10—C11—C12	−139.59 (14)
C1—C2—C3—C4	−1.3 (3)	N4—C11—C12—C13	−156.04 (19)
C1—C2—C3—Cl1	178.71 (16)	C10—C11—C12—C13	22.0 (3)
C2—C3—C4—C5	0.8 (4)	N4—C11—C12—S2	16.7 (2)
Cl1—C3—C4—C5	−179.26 (18)	C10—C11—C12—S2	−165.26 (13)
C3—C4—C5—C6	1.1 (4)	C15—S2—C12—C13	−0.15 (16)
C7—O1—C6—C5	161.28 (18)	C15—S2—C12—C11	−174.03 (15)
C7—O1—C6—C1	−19.9 (3)	C11—C12—C13—C14	173.10 (18)
C4—C5—C6—O1	176.5 (2)	S2—C12—C13—C14	−0.1 (2)
C4—C5—C6—C1	−2.4 (3)	C12—C13—C14—C15	0.4 (3)
C2—C1—C6—O1	−176.98 (18)	C12—C13—C14—N5	−176.46 (18)
C2—C1—C6—C5	1.8 (3)	O3—N5—C14—C15	−178.6 (2)
C6—O1—C7—C8	−172.11 (16)	O2—N5—C14—C15	1.6 (4)
N2—N1—C8—N3	−0.7 (2)	O3—N5—C14—C13	−2.0 (3)
N2—N1—C8—C7	−174.39 (17)	O2—N5—C14—C13	178.2 (2)
C9—N3—C8—N1	1.1 (2)	C13—C14—C15—S2	−0.5 (2)
N4—N3—C8—N1	174.43 (16)	N5—C14—C15—S2	176.31 (17)
C9—N3—C8—C7	174.73 (17)	C12—S2—C15—C14	0.37 (16)
N4—N3—C8—C7	−12.0 (3)	C11—C10—C16—C17	177.31 (17)
O1—C7—C8—N1	−132.7 (2)	S1—C10—C16—C17	−0.9 (3)
O1—C7—C8—N3	54.6 (3)	C10—C16—C17—C22	39.3 (3)
N1—N2—C9—N3	0.8 (2)	C10—C16—C17—C18	−141.3 (2)
N1—N2—C9—S1	−177.89 (13)	C22—C17—C18—C19	−2.3 (3)
C8—N3—C9—N2	−1.18 (19)	C16—C17—C18—C19	178.31 (18)
N4—N3—C9—N2	−174.25 (16)	C17—C18—C19—C20	0.9 (3)
C8—N3—C9—S1	177.59 (13)	C18—C19—C20—C21	0.7 (3)
N4—N3—C9—S1	4.5 (2)	C18—C19—C20—Cl2	179.75 (16)
C10—S1—C9—N2	−155.83 (17)	C19—C20—C21—C22	−0.8 (3)
C10—S1—C9—N3	25.61 (15)	Cl2—C20—C21—C22	−179.87 (15)
C9—S1—C10—C16	135.40 (16)	C20—C21—C22—C17	−0.6 (3)
C9—S1—C10—C11	−42.97 (14)	C18—C17—C22—C21	2.2 (3)
N3—N4—C11—C12	175.41 (15)	C16—C17—C22—C21	−178.45 (18)
N3—N4—C11—C10	−2.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N2ⁱ	0.93	2.60	3.495 (3)	162
C21—H21A···Cl1ⁱⁱ	0.93	2.81	3.691 (2)	159

Symmetry codes: (i) x+1, y+1, z; (ii) x, y−1, z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₃Cl₂N₅O₃S₂
M_r	530.39
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.5021 (2), 10.0379 (2), 14.3623 (3)
α, β, γ (°)	94.434 (1), 97.981 (1), 109.242 (1)
V (Å³)	1136.07 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.39 × 0.32 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.827, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	19590, 6548, 5142
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.133, 1.04
No. of reflections	6548
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.46

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N2ⁱ	0.93	2.60	3.495 (3)	162
C21—H21A···Cl1ⁱⁱ	0.93	2.81	3.691 (2)	159

Symmetry codes: (i) x+1, y+1, z; (ii) x, y−1, z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF, SIJA and IAR thank Universiti Sains Malaysia for the Research University Grants (Nos.1001/PFIZIK/811160 and 1001/PFIZIK/811151).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010a). Acta Cryst. E66, o1303. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010b). Acta Cryst. E66, o1394–o1395. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010c). Acta Cryst. E66, o2162–o2163. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra, & Kalluraya, B. (2010d). Acta Cryst. E66, o2178–o2179. Google Scholar
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Volume 67| Part 5| May 2011| Pages o1266-o1267

doi:10.1107/S1600536811015637

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

7-(4-Chloro­benzyl­­idene)-3-[(4-chloro­phen­­oxy)meth­yl]-6-(4-nitro­thio­phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

7-(4-Chlorobenzylidene)-3-[(4-chlorophenoxy)methyl]-6-(4-nitrothiophen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine