1-(Benzothia­zol-2-yl)-3-(4-nitro­benzo­yl)thio­urea

Saeed, S.; Rashid, N.; Hussain, R.; Jones, P.G.

doi:10.1107/S1600536809030803

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2106

doi:10.1107/S1600536809030803

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1-(Benzothiazol-2-yl)-3-(4-nitrobenzoyl)thiourea

Sohail Saeed,^a ^* Naghmana Rashid,^a Rizwan Hussain ^b and Peter G. Jones ^c

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad, Pakistan, ^bDirectorate of Chemical & Power Sources, National Development Complex, PO Box 2216, Islamabad, Pakistan, and ^cInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 29 July 2009; accepted 3 August 2009; online 8 August 2009)

The molecule of the title compound, C₁₅H₁₀N₄O₃S₂, is almost planar (r.m.s. deviation = 0.1Å for all non-H atoms). An intramolecular N—H⋯O=C hydrogen bond is observed. In the crystal, molecules are connected into layers parallel to (10 $[\overline{1}]$ ) by a classical intermolecular hydrogen bond from the second NH group to a nitro O atom and by three weak hydrogen bonds of the C—H⋯X type (X = O or S_thione).

Related literature

For general background to the chemistry of thiourea derivatives, see Choi et al. (2008 ); Jones et al. (2008 ); Su et al. (2006 ). For related structures, see: Saeed et al. (2008a ,b ,c ); Yunus et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₀N₄O₃S₂
M_r = 358.39
Monoclinic, P 2₁ /n
a = 7.1596 (3) Å
b = 17.9071 (5) Å
c = 11.5768 (4) Å
β = 96.446 (4)°
V = 1474.85 (9) Å³
Z = 4
Cu Kα radiation
μ = 3.50 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction, Yarnton, England.]$ ) T_min = 0.682, T_max = 1.000 (expected range = 0.573–0.840)
30943 measured reflections
3026 independent reflections
2834 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.078
S = 1.06
3026 reflections
225 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1	0.83 (2)	1.92 (2)	2.598 (2)	138 (2)
N2—H02⋯O2ⁱ	0.84 (2)	2.42 (2)	3.261 (2)	175 (2)
C5—H5⋯O1ⁱⁱ	0.95	2.55	3.462 (2)	161
C11—H11⋯O2ⁱ	0.95	2.41	3.318 (2)	159
C12—H12⋯S2ⁱⁱⁱ	0.95	2.73	3.673 (1)	173
C7—H7⋯S2^iv	0.95	2.91	3.563 (1)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+2.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030803/im2131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030803/im2131Isup2.hkl

checkCIF report

Comment top

Thiourea and its derivatives have found extensive applications in the field of medicine, agriculture and analytical chemistry. They are known to exhibit a wide variety of biological activities such as antiviral, anti-bacterial, antifungal, antitubercular, herbicidal, insecticidal and some epoxy resin curing agents containing amino functional groups (Saeed et al., 2008a,b,c). They have found broad areas of application e.g. in anion recognition, nonlinear optics and catalysis, and also display good coordination abilities (Choi et al., 2008; Jones et al., 2008; Su et al., 2006). As part of our research on coordination chemistry of thioureas, we are interested in the study of the influence of non-covalent interactions, especially hydrogen bonds and π-π stacking interactions, on the coordination modes of benzothiazoles bearing the 4- nitrobenzoylthiourea group with transition metal ions. Such coordination compounds of thiourea have been studied for various biological systems like antibactrial, antifungal and anticancer activities (Yunus et al., 2008).The importance of such work lies in the possibility that the next generation of thiourea derivatives might be more efficacious as antimicrobial and anticancer agents. However, a thorough investigation relating structure and activity of thiourea derivatives as well as their stability under biological conditions is required. These detailed investigations could be helpful in designing more potent antimicrobial and anticancer agents for therapeutic use. Condensation of acyl or aroyl thiocyanates with primary amines affords 1, 3-disubstituted thioureas in excellent yields in a single step. In the present paper, the crystal structure of the title compound is reported.

The molecule of the title compound is shown in Fig. 1. The molecule is approximately planar (r.m.s. deviation for all non-H atoms 0.1 Å). The two ring systems (S1–C7A plus N1, C8, N2; C10–C15 plus N4, C9) are essentially parallel (interplanar angle 1.06 (3)°), because non-zero torsion angles such as C11—C10—C9—N2 - 10.7 (2) and N1—C8—N2—C9 7.7 (2)° effectively cancel out.

An intramolecular hydrogen bond N1—H01···O1 is observed. The second classical H bond N2—H02···O2 combines with the three shortest "weak" H bonds H5···O1, H11···O2 and H12···S2 (Table 1) to form layers parallel to (101) (Fig. 2).

Related literature top

For general background to the chemistry of thiourea derivatives, see Choi et al. (2008); Jones et al. (2008); Su et al. (2006). For related structures, see: Saeed et al. (2008a,b,c); Yunus et al. (2008).

Experimental top

A mixture of ammonium thiocyanate (0.1 mol) and 4-nitrobenzoyl chloride (0.1 mol) in anhydrous acetone (60 ml) was stirred for 40 min. 2-Aminobenzothiazole (0.1 mol) was added and the reaction mixture was refluxed for 2 h. After cooling, the reaction mixture was poured into 800 ml of acidified cold water (pH = 5). The resulting dark yellow solid was filtered and washed with cold acetone (yield 1.56 g, 87%). The title compound (I) was obtained as suitable crystals for X-ray analysis after recrystallization of the solid from a 1:1 ethanol- dichloromethane mixture.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound in the crystal. Ellipsoids correspond to 50% probability levels.
	Fig. 2. Packing diagram of the title compound viewed perpendicular to (101). Thin dashed lines represent "weak" and thick dashed lines classical H bonds. H atoms not involved in H bonds are omitted for clarity.

1-(Benzothiazol-2-yl)-3-(4-nitrobenzoyl)thiourea top

Crystal data top

C₁₅H₁₀N₄O₃S₂	F(000) = 736
M_r = 358.39	D_x = 1.614 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 21284 reflections
a = 7.1596 (3) Å	θ = 3.8–75.7°
b = 17.9071 (5) Å	µ = 3.50 mm⁻¹
c = 11.5768 (4) Å	T = 100 K
β = 96.446 (4)°	Lath, yellow
V = 1474.85 (9) Å³	0.20 × 0.10 × 0.05 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Nova A diffractometer	3026 independent reflections
Radiation source: Nova (Cu) X-ray Source	2834 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.3543 pixels mm^-1	θ_max = 75.9°, θ_min = 4.6°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −22→22
T_min = 0.682, T_max = 1.000	l = −14→14
30943 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0427P)² + 0.7178P] where P = (F_o² + 2F_c²)/3
3026 reflections	(Δ/σ)_max = 0.001
225 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₀N₄O₃S₂	V = 1474.85 (9) Å³
M_r = 358.39	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 7.1596 (3) Å	µ = 3.50 mm⁻¹
b = 17.9071 (5) Å	T = 100 K
c = 11.5768 (4) Å	0.20 × 0.10 × 0.05 mm
β = 96.446 (4)°

Data collection top

Oxford Diffraction Xcalibur Nova A diffractometer	3026 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2834 reflections with I > 2σ(I)
T_min = 0.682, T_max = 1.000	R_int = 0.040
30943 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.28 e Å⁻³
3026 reflections	Δρ_min = −0.25 e Å⁻³
225 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
S1	0.53606 (4)	0.470055 (17)	0.84776 (3)	0.01726 (10)
C2	0.44766 (17)	0.43337 (7)	0.71218 (11)	0.0165 (3)
N3	0.45826 (16)	0.36156 (6)	0.69808 (10)	0.0194 (2)
C3A	0.54057 (19)	0.32891 (8)	0.80022 (12)	0.0190 (3)
C4	0.5778 (2)	0.25256 (8)	0.81532 (13)	0.0232 (3)
H4	0.5452	0.2182	0.7538	0.028*
C5	0.6629 (2)	0.22814 (8)	0.92178 (13)	0.0248 (3)
H5	0.6894	0.1765	0.9331	0.030*
C6	0.7108 (2)	0.27842 (8)	1.01331 (12)	0.0234 (3)
H6	0.7681	0.2602	1.0859	0.028*
C7	0.67605 (19)	0.35414 (8)	0.99963 (12)	0.0209 (3)
H7	0.7094	0.3883	1.0614	0.025*
C7A	0.59024 (18)	0.37870 (7)	0.89188 (12)	0.0178 (3)
S2	0.43025 (6)	0.610190 (19)	0.71210 (3)	0.02877 (12)
N1	0.36489 (16)	0.47552 (6)	0.61966 (10)	0.0173 (2)
H01	0.316 (3)	0.4498 (11)	0.5646 (16)	0.029 (5)*
N2	0.25433 (16)	0.57570 (6)	0.50564 (10)	0.0179 (2)
H02	0.260 (3)	0.6224 (11)	0.5014 (16)	0.028 (5)*
N4	−0.17337 (16)	0.67589 (7)	0.00397 (10)	0.0215 (2)
O1	0.15674 (15)	0.46515 (5)	0.42156 (8)	0.0227 (2)
O2	−0.20909 (16)	0.74281 (6)	0.00649 (9)	0.0300 (3)
O3	−0.19731 (17)	0.63730 (6)	−0.08377 (9)	0.0314 (3)
C8	0.34765 (18)	0.55045 (7)	0.61124 (12)	0.0183 (3)
C9	0.16239 (18)	0.53355 (7)	0.41710 (11)	0.0174 (3)
C10	0.07004 (18)	0.57425 (7)	0.31352 (11)	0.0168 (3)
C11	0.04521 (19)	0.65149 (7)	0.30881 (12)	0.0194 (3)
H11	0.0855	0.6812	0.3749	0.023*
C12	−0.03826 (19)	0.68511 (8)	0.20783 (12)	0.0200 (3)
H12	−0.0567	0.7376	0.2040	0.024*
C13	−0.09376 (18)	0.64017 (7)	0.11316 (11)	0.0177 (3)
C14	−0.07437 (19)	0.56315 (8)	0.11565 (11)	0.0188 (3)
H14	−0.1166	0.5338	0.0495	0.023*
C15	0.00793 (19)	0.53013 (7)	0.21676 (12)	0.0186 (3)
H15	0.0224	0.4774	0.2207	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01993 (17)	0.01434 (16)	0.01670 (17)	0.00078 (11)	−0.00157 (12)	0.00075 (10)
C2	0.0163 (6)	0.0159 (6)	0.0173 (6)	−0.0001 (5)	0.0017 (5)	0.0013 (5)
N3	0.0218 (6)	0.0165 (6)	0.0194 (5)	0.0011 (4)	−0.0001 (4)	0.0017 (4)
C3A	0.0190 (6)	0.0186 (7)	0.0192 (6)	0.0002 (5)	0.0017 (5)	0.0028 (5)
C4	0.0278 (7)	0.0171 (7)	0.0240 (7)	0.0003 (5)	0.0005 (6)	0.0008 (5)
C5	0.0277 (7)	0.0180 (7)	0.0284 (7)	0.0024 (5)	0.0022 (6)	0.0072 (6)
C6	0.0237 (7)	0.0235 (7)	0.0222 (7)	0.0015 (5)	−0.0001 (5)	0.0076 (5)
C7	0.0205 (7)	0.0224 (7)	0.0192 (6)	0.0001 (5)	−0.0002 (5)	0.0018 (5)
C7A	0.0161 (6)	0.0164 (6)	0.0209 (6)	0.0011 (5)	0.0021 (5)	0.0023 (5)
S2	0.0467 (2)	0.01438 (18)	0.02184 (19)	−0.00151 (14)	−0.01103 (15)	0.00050 (12)
N1	0.0206 (6)	0.0145 (5)	0.0159 (5)	0.0002 (4)	−0.0023 (4)	0.0008 (4)
N2	0.0224 (6)	0.0122 (5)	0.0183 (5)	0.0002 (4)	−0.0014 (4)	0.0016 (4)
N4	0.0201 (6)	0.0226 (6)	0.0206 (6)	−0.0019 (4)	−0.0025 (4)	0.0037 (5)
O1	0.0314 (5)	0.0138 (4)	0.0214 (5)	0.0004 (4)	−0.0037 (4)	0.0006 (4)
O2	0.0372 (6)	0.0211 (5)	0.0294 (6)	0.0048 (4)	−0.0073 (5)	0.0060 (4)
O3	0.0439 (7)	0.0301 (6)	0.0182 (5)	−0.0027 (5)	−0.0059 (4)	−0.0006 (4)
C8	0.0190 (6)	0.0174 (6)	0.0182 (6)	0.0002 (5)	0.0012 (5)	0.0023 (5)
C9	0.0177 (6)	0.0168 (6)	0.0179 (6)	0.0006 (5)	0.0027 (5)	0.0000 (5)
C10	0.0156 (6)	0.0162 (6)	0.0186 (6)	−0.0008 (5)	0.0019 (5)	0.0008 (5)
C11	0.0220 (7)	0.0160 (6)	0.0190 (6)	−0.0003 (5)	−0.0024 (5)	−0.0019 (5)
C12	0.0215 (6)	0.0149 (6)	0.0227 (7)	0.0008 (5)	−0.0015 (5)	0.0002 (5)
C13	0.0162 (6)	0.0194 (6)	0.0168 (6)	0.0001 (5)	−0.0007 (5)	0.0026 (5)
C14	0.0191 (6)	0.0194 (6)	0.0178 (6)	−0.0012 (5)	0.0011 (5)	−0.0018 (5)
C15	0.0204 (6)	0.0143 (6)	0.0210 (7)	−0.0006 (5)	0.0015 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

S1—C7A	1.7443 (13)	O1—C9	1.2269 (16)
S1—C2	1.7529 (13)	C9—C10	1.4927 (18)
C2—N3	1.2994 (18)	C10—C11	1.3949 (19)
C2—N1	1.3877 (17)	C10—C15	1.4017 (19)
N3—C3A	1.3896 (17)	C11—C12	1.3890 (18)
C3A—C4	1.4002 (19)	C12—C13	1.3815 (19)
C3A—C7A	1.4009 (19)	C13—C14	1.3863 (19)
C4—C5	1.383 (2)	C14—C15	1.3828 (19)
C5—C6	1.403 (2)	C4—H4	0.9500
C6—C7	1.385 (2)	C5—H5	0.9500
C7—C7A	1.3982 (18)	C6—H6	0.9500
S2—C8	1.6439 (14)	C7—H7	0.9500
N1—C8	1.3499 (17)	N1—H01	0.832 (19)
N2—C9	1.3791 (17)	N2—H02	0.84 (2)
N2—C8	1.4007 (17)	C11—H11	0.9500
N4—O3	1.2246 (16)	C12—H12	0.9500
N4—O2	1.2264 (16)	C14—H14	0.9500
N4—C13	1.4731 (16)	C15—H15	0.9500

C7A—S1—C2	87.52 (6)	C15—C10—C9	116.03 (11)
N3—C2—N1	117.86 (12)	C12—C11—C10	120.24 (12)
N3—C2—S1	117.58 (10)	C13—C12—C11	118.26 (12)
N1—C2—S1	124.55 (10)	C12—C13—C14	122.94 (12)
C2—N3—C3A	109.55 (11)	C12—C13—N4	118.49 (12)
N3—C3A—C4	125.00 (13)	C14—C13—N4	118.56 (12)
N3—C3A—C7A	115.09 (12)	C15—C14—C13	118.37 (12)
C4—C3A—C7A	119.89 (12)	C14—C15—C10	120.15 (12)
C5—C4—C3A	118.59 (13)	C5—C4—H4	120.7
C4—C5—C6	121.06 (13)	C3A—C4—H4	120.7
C7—C6—C5	121.08 (13)	C4—C5—H5	119.5
C6—C7—C7A	117.75 (13)	C6—C5—H5	119.5
C7—C7A—C3A	121.62 (12)	C7—C6—H6	119.5
C7—C7A—S1	128.12 (11)	C5—C6—H6	119.5
C3A—C7A—S1	110.23 (10)	C6—C7—H7	121.1
C8—N1—C2	128.62 (12)	C7A—C7—H7	121.1
C9—N2—C8	127.82 (11)	C8—N1—H01	117.8 (13)
O3—N4—O2	124.13 (12)	C2—N1—H01	113.5 (13)
O3—N4—C13	118.13 (11)	C9—N2—H02	121.6 (13)
O2—N4—C13	117.74 (11)	C8—N2—H02	110.6 (13)
N1—C8—N2	114.50 (12)	C12—C11—H11	119.9
N1—C8—S2	124.95 (10)	C10—C11—H11	119.9
N2—C8—S2	120.54 (10)	C13—C12—H12	120.9
O1—C9—N2	122.03 (12)	C11—C12—H12	120.9
O1—C9—C10	120.50 (12)	C15—C14—H14	120.8
N2—C9—C10	117.47 (11)	C13—C14—H14	120.8
C11—C10—C15	120.00 (12)	C14—C15—H15	119.9
C11—C10—C9	123.96 (12)	C10—C15—H15	119.9

C7A—S1—C2—N3	−1.03 (11)	C9—N2—C8—N1	7.7 (2)
C7A—S1—C2—N1	177.99 (12)	C9—N2—C8—S2	−173.54 (11)
N1—C2—N3—C3A	−178.55 (11)	C8—N2—C9—O1	−1.8 (2)
S1—C2—N3—C3A	0.54 (15)	C8—N2—C9—C10	178.80 (12)
C2—N3—C3A—C4	−178.51 (13)	O1—C9—C10—C11	169.88 (13)
C2—N3—C3A—C7A	0.44 (16)	N2—C9—C10—C11	−10.69 (19)
N3—C3A—C4—C5	179.12 (13)	O1—C9—C10—C15	−10.64 (19)
C7A—C3A—C4—C5	0.2 (2)	N2—C9—C10—C15	168.79 (12)
C3A—C4—C5—C6	0.3 (2)	C15—C10—C11—C12	−1.0 (2)
C4—C5—C6—C7	−0.6 (2)	C9—C10—C11—C12	178.44 (12)
C5—C6—C7—C7A	0.5 (2)	C10—C11—C12—C13	−0.5 (2)
C6—C7—C7A—C3A	0.0 (2)	C11—C12—C13—C14	1.8 (2)
C6—C7—C7A—S1	−177.83 (11)	C11—C12—C13—N4	−176.88 (12)
N3—C3A—C7A—C7	−179.35 (12)	O3—N4—C13—C12	169.77 (12)
C4—C3A—C7A—C7	−0.3 (2)	O2—N4—C13—C12	−9.23 (19)
N3—C3A—C7A—S1	−1.19 (15)	O3—N4—C13—C14	−8.94 (19)
C4—C3A—C7A—S1	177.82 (11)	O2—N4—C13—C14	172.05 (12)
C2—S1—C7A—C7	179.17 (13)	C12—C13—C14—C15	−1.4 (2)
C2—S1—C7A—C3A	1.17 (10)	N4—C13—C14—C15	177.23 (12)
N3—C2—N1—C8	−175.86 (13)	C13—C14—C15—C10	−0.2 (2)
S1—C2—N1—C8	5.1 (2)	C11—C10—C15—C14	1.4 (2)
C2—N1—C8—N2	−179.42 (12)	C9—C10—C15—C14	−178.12 (12)
C2—N1—C8—S2	1.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1	0.83 (2)	1.92 (2)	2.598 (2)	138 (2)
N2—H02···O2ⁱ	0.84 (2)	2.42 (2)	3.261 (2)	175 (2)
C5—H5···O1ⁱⁱ	0.95	2.55	3.462 (2)	161
C11—H11···O2ⁱ	0.95	2.41	3.318 (2)	159
C12—H12···S2ⁱⁱⁱ	0.95	2.73	3.673 (1)	173
C7—H7···S2^iv	0.95	2.91	3.563 (1)	127

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₄O₃S₂
M_r	358.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.1596 (3), 17.9071 (5), 11.5768 (4)
β (°)	96.446 (4)
V (Å³)	1474.85 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.50
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur Nova A diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.682, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	30943, 3026, 2834
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.078, 1.06
No. of reflections	3026
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1	0.83 (2)	1.92 (2)	2.598 (2)	138 (2)
N2—H02···O2ⁱ	0.84 (2)	2.42 (2)	3.261 (2)	175 (2)
C5—H5···O1ⁱⁱ	0.95	2.55	3.462 (2)	161.0
C11—H11···O2ⁱ	0.95	2.41	3.318 (2)	158.8
C12—H12···S2ⁱⁱⁱ	0.95	2.73	3.673 (1)	172.8
C7—H7···S2^iv	0.95	2.91	3.563 (1)	127.0

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+2.

Acknowledgements

The authors are grateful to Allama Iqbal Open University and the National Development Complex, Islamabad, Pakistan for the allocation of research and analytical laboratory facilities.

References

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