1-[2-(2,4-Dinitro­benzyl­ideneamino)phen­yl]-3-phenyl­thio­urea

Umadevi, M.; Devaraj, S.; Kandaswamy, M.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809035880

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2447

doi:10.1107/S1600536809035880

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1-[2-(2,4-Dinitrobenzylideneamino)phenyl]-3-phenylthiourea

M. Umadevi,^a S. Devaraj,^b M. Kandaswamy,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, Tamilnadu, India, ^bDeparment of Inorganic Chemistry, School of Chemical Sceinces, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamilnadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 2 September 2009; accepted 4 September 2009; online 12 September 2009)

In the title compound, C₂₀H₁₅N₅O₄S, the central benzene ring makes dihedral angles of 59.5 (1) and 51.7 (1)°, respectively, with the terminal phenyl and benzene rings. The molecular structure exhibits weak intramolecular N—H⋯N and C—H⋯S interactions. In the crystal structure, molecules are linked by weak intermolecular N—H⋯S and C—H⋯O interactions, forming a chain along [1 $[\overline{1}]$ 1].

Related literature

For the biological activity of thioureas, see: Huebner et al. (1953 ); Madan & Taneja (1991 ); Manjula et al. (2009 ). For related structures, see: Gayathri et al. (2007 , 2008 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₅N₅O₄S
M_r = 421.43
Monoclinic, P 2₁ /c
a = 8.362 (5) Å
b = 18.767 (3) Å
c = 12.379 (4) Å
β = 94.827 (5)°
V = 1935.7 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.20 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.960, T_max = 0.968
28336 measured reflections
6878 independent reflections
4509 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.02
6878 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N3	0.86	2.14	2.614 (2)	114
C3—H3⋯S1	0.93	2.55	3.215 (2)	128
N4—H4A⋯N3	0.86	2.14	2.614 (2)	114
N5—H5A⋯S1ⁱ	0.86	2.49	3.284 (2)	155
C12—H12⋯O3ⁱⁱ	0.93	2.57	3.397 (3)	148
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035880/is2457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035880/is2457Isup2.hkl

checkCIF report

Comment top

Thioureas are known to exhibit antiviral, antibacterial, anticancer (Madan & Taneja, 1991; Manjula et al., 2009), antifungal, antitubercular, antithyroidal, herbicidal and insecticidal (Huebner et al., 1953) activities.

The geometric parameters in (I), (Fig. 1) agree with the reported values of similar structures (Gayathri et al., 2007, 2008). The benzene ring C1—C6 makes the dihedral angle of 59.5 (1)° with the phenyl ring C15—C20 and 51.7 (1)° with the dinitrobenzene ring C8—C13.

The molecular structure of (I) exhibits weak intramolecular N—H···N, C—H···S and C—H···O interactions and the crystal structure is stabilized by weak intermolecular N—H···S and C—H···O interactions (Table 1 and Fig. 2). The intermolecular N5—H5A···S1 interaction generates an eight-membered ring, with graph-set motif R₂²(8) and the C12—H12···O3 interaction generates a ten-membered ring, with graph-set motif R₂²(10) (Bernstein, 1995).

Related literature top

For the biological activity of thioureas, see: Huebner et al. (1953); Madan & Taneja (1991); Manjula et al. (2009). For related structures, see: Gayathri et al. (2007, 2008). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To the solution of 1-(2-aminophenyl)-3-phenylthiourea (0.3 g, 1.2 mmol) in methanol (25 ml), 2,4-dinitrobenzaldehyde (0.36 g, 1.2 mmol) in methanol (25 ml) was added under stirring. The resulting mixture was refluxed for 3 h and cooled to room temperature. The solid product was collected by filtration and washed with cold methanol. The microcrystalline compound was recrystallized from hot chloroform.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

1-[2-(2,4-Dinitrobenzylideneamino)phenyl]-3-phenylthiourea top

Crystal data top

C₂₀H₁₅N₅O₄S	F(000) = 872
M_r = 421.43	D_x = 1.446 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9702 reflections
a = 8.362 (5) Å	θ = 2.2–32.3°
b = 18.767 (3) Å	µ = 0.21 mm⁻¹
c = 12.379 (4) Å	T = 295 K
β = 94.827 (5)°	Prism, orange
V = 1935.7 (14) Å³	0.20 × 0.16 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	6878 independent reflections
Radiation source: fine-focus sealed tube	4509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scans	θ_max = 32.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.960, T_max = 0.968	k = −28→26
28336 measured reflections	l = −9→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0628P)² + 0.3472P] where P = (F_o² + 2F_c²)/3
6878 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₀H₁₅N₅O₄S	V = 1935.7 (14) Å³
M_r = 421.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.362 (5) Å	µ = 0.21 mm⁻¹
b = 18.767 (3) Å	T = 295 K
c = 12.379 (4) Å	0.20 × 0.16 × 0.16 mm
β = 94.827 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	6878 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4509 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.968	R_int = 0.028
28336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	Δρ_max = 0.25 e Å⁻³
6878 reflections	Δρ_min = −0.37 e Å⁻³
271 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.62398 (16)	0.29698 (7)	0.34283 (10)	0.0381 (3)
C2	0.65955 (15)	0.23913 (7)	0.41328 (9)	0.0360 (3)
C3	0.76661 (18)	0.24941 (8)	0.50420 (11)	0.0448 (3)
H3	0.7860	0.2127	0.5541	0.054*
C4	0.84381 (19)	0.31360 (9)	0.52044 (12)	0.0511 (4)
H4	0.9149	0.3200	0.5816	0.061*
C5	0.8174 (2)	0.36867 (9)	0.44751 (13)	0.0560 (4)
H5	0.8740	0.4111	0.4576	0.067*
C6	0.70627 (19)	0.36049 (8)	0.35919 (12)	0.0496 (4)
H6	0.6868	0.3979	0.3106	0.060*
C7	0.42126 (16)	0.33645 (8)	0.21914 (10)	0.0412 (3)
H7	0.4321	0.3809	0.2522	0.049*
C8	0.30541 (16)	0.32650 (7)	0.12401 (10)	0.0381 (3)
C9	0.32496 (18)	0.26958 (8)	0.05491 (11)	0.0459 (3)
H9	0.4040	0.2359	0.0739	0.055*
C10	0.23061 (19)	0.26145 (9)	−0.04113 (11)	0.0478 (3)
H10	0.2441	0.2225	−0.0859	0.057*
C11	0.11616 (16)	0.31229 (8)	−0.06909 (10)	0.0425 (3)
C12	0.08777 (17)	0.36881 (8)	−0.00335 (11)	0.0424 (3)
H12	0.0087	0.4023	−0.0234	0.051*
C13	0.18123 (16)	0.37421 (8)	0.09399 (10)	0.0393 (3)
C14	0.57689 (16)	0.11081 (7)	0.42739 (10)	0.0387 (3)
C15	0.41735 (19)	0.06746 (7)	0.26115 (11)	0.0435 (3)
C16	0.2548 (2)	0.05512 (8)	0.24467 (12)	0.0471 (3)
H16	0.1955	0.0457	0.3034	0.057*
C17	0.1798 (2)	0.05672 (10)	0.14094 (14)	0.0606 (4)
H17	0.0700	0.0482	0.1298	0.073*
C18	0.2668 (3)	0.07077 (10)	0.05446 (13)	0.0687 (5)
H18	0.2161	0.0721	−0.0153	0.082*
C19	0.4278 (3)	0.08286 (11)	0.07051 (14)	0.0703 (5)
H19	0.4862	0.0923	0.0114	0.084*
C20	0.5058 (2)	0.08133 (10)	0.17423 (13)	0.0599 (4)
H20	0.6157	0.0895	0.1849	0.072*
N1	0.01932 (16)	0.30558 (9)	−0.17349 (10)	0.0534 (3)
N2	0.14010 (17)	0.43172 (8)	0.16707 (11)	0.0542 (3)
N3	0.50634 (14)	0.28461 (6)	0.25608 (9)	0.0406 (3)
N4	0.58017 (14)	0.17574 (6)	0.38222 (8)	0.0409 (3)
H4A	0.5216	0.1791	0.3219	0.049*
N5	0.49272 (17)	0.06127 (7)	0.36821 (10)	0.0529 (3)
H5A	0.4832	0.0206	0.3990	0.064*
O1	0.0455 (2)	0.25501 (10)	−0.23077 (11)	0.0917 (5)
O2	−0.08088 (15)	0.35115 (8)	−0.19739 (9)	0.0652 (3)
O3	0.0704 (2)	0.48301 (8)	0.12851 (13)	0.0930 (5)
O4	0.1705 (2)	0.42321 (9)	0.26429 (11)	0.0902 (5)
S1	0.66368 (5)	0.08789 (2)	0.55035 (3)	0.04838 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0389 (7)	0.0402 (7)	0.0341 (5)	0.0022 (5)	−0.0038 (5)	0.0060 (5)
C2	0.0366 (7)	0.0377 (7)	0.0330 (5)	0.0040 (5)	−0.0017 (5)	0.0047 (5)
C3	0.0487 (8)	0.0449 (8)	0.0384 (6)	0.0049 (6)	−0.0100 (5)	0.0062 (5)
C4	0.0529 (9)	0.0506 (9)	0.0465 (7)	0.0005 (7)	−0.0159 (6)	−0.0013 (6)
C5	0.0595 (10)	0.0439 (8)	0.0609 (9)	−0.0082 (7)	−0.0171 (7)	0.0021 (7)
C6	0.0544 (9)	0.0403 (8)	0.0516 (8)	−0.0045 (6)	−0.0108 (6)	0.0107 (6)
C7	0.0429 (7)	0.0426 (7)	0.0368 (6)	0.0018 (6)	−0.0041 (5)	0.0065 (5)
C8	0.0371 (7)	0.0428 (7)	0.0335 (5)	0.0017 (5)	−0.0012 (5)	0.0091 (5)
C9	0.0442 (8)	0.0509 (8)	0.0416 (6)	0.0108 (6)	−0.0018 (5)	0.0056 (6)
C10	0.0498 (8)	0.0550 (9)	0.0381 (6)	0.0062 (7)	0.0015 (6)	−0.0022 (6)
C11	0.0374 (7)	0.0572 (9)	0.0322 (5)	−0.0021 (6)	−0.0015 (5)	0.0077 (5)
C12	0.0375 (7)	0.0482 (8)	0.0405 (6)	0.0042 (6)	−0.0030 (5)	0.0106 (5)
C13	0.0403 (7)	0.0408 (7)	0.0364 (6)	0.0024 (6)	0.0002 (5)	0.0062 (5)
C14	0.0401 (7)	0.0392 (7)	0.0364 (6)	0.0017 (5)	−0.0001 (5)	0.0072 (5)
C15	0.0586 (9)	0.0340 (7)	0.0369 (6)	−0.0010 (6)	−0.0032 (6)	0.0032 (5)
C16	0.0558 (9)	0.0397 (7)	0.0455 (7)	0.0040 (7)	0.0019 (6)	−0.0005 (6)
C17	0.0665 (11)	0.0515 (10)	0.0602 (9)	0.0048 (8)	−0.0163 (8)	−0.0025 (7)
C18	0.1052 (16)	0.0567 (11)	0.0405 (7)	0.0006 (10)	−0.0150 (8)	−0.0024 (7)
C19	0.1034 (17)	0.0702 (12)	0.0388 (7)	−0.0056 (11)	0.0143 (9)	0.0021 (7)
C20	0.0657 (11)	0.0657 (11)	0.0489 (8)	−0.0085 (9)	0.0079 (7)	0.0050 (7)
N1	0.0498 (7)	0.0732 (10)	0.0357 (5)	−0.0006 (7)	−0.0040 (5)	0.0038 (6)
N2	0.0549 (8)	0.0525 (8)	0.0531 (7)	0.0126 (6)	−0.0072 (6)	−0.0041 (6)
N3	0.0413 (6)	0.0429 (6)	0.0360 (5)	−0.0013 (5)	−0.0064 (4)	0.0103 (4)
N4	0.0464 (6)	0.0384 (6)	0.0358 (5)	−0.0013 (5)	−0.0096 (4)	0.0074 (4)
N5	0.0704 (9)	0.0438 (7)	0.0420 (6)	−0.0131 (6)	−0.0106 (6)	0.0141 (5)
O1	0.1080 (12)	0.1083 (13)	0.0534 (7)	0.0283 (10)	−0.0248 (7)	−0.0255 (8)
O2	0.0583 (7)	0.0850 (9)	0.0490 (6)	0.0074 (6)	−0.0157 (5)	0.0116 (6)
O3	0.1231 (13)	0.0625 (9)	0.0886 (10)	0.0423 (9)	−0.0200 (9)	−0.0069 (7)
O4	0.1129 (13)	0.1065 (12)	0.0489 (7)	0.0467 (10)	−0.0073 (7)	−0.0162 (7)
S1	0.0547 (2)	0.0481 (2)	0.04016 (17)	−0.00134 (16)	−0.00860 (14)	0.01530 (14)

Geometric parameters (Å, º) top

C1—C6	1.383 (2)	C12—H12	0.9300
C1—C2	1.4085 (17)	C13—N2	1.468 (2)
C1—N3	1.4132 (16)	C14—N4	1.3419 (17)
C2—C3	1.3914 (18)	C14—N5	1.3452 (19)
C2—N4	1.4003 (17)	C14—S1	1.6860 (13)
C3—C4	1.374 (2)	C15—C16	1.377 (2)
C3—H3	0.9300	C15—C20	1.381 (2)
C4—C5	1.378 (2)	C15—N5	1.4236 (17)
C4—H4	0.9300	C16—C17	1.381 (2)
C5—C6	1.383 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.370 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—N3	1.2678 (17)	C18—C19	1.363 (3)
C7—C8	1.4725 (18)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.391 (2)
C8—C9	1.387 (2)	C19—H19	0.9300
C8—C13	1.3975 (19)	C20—H20	0.9300
C9—C10	1.379 (2)	N1—O1	1.215 (2)
C9—H9	0.9300	N1—O2	1.2162 (19)
C10—C11	1.375 (2)	N2—O3	1.2031 (18)
C10—H10	0.9300	N2—O4	1.2194 (18)
C11—C12	1.370 (2)	N4—H4A	0.8600
C11—N1	1.4716 (17)	N5—H5A	0.8600
C12—C13	1.3837 (18)

C6—C1—C2	119.82 (12)	C12—C13—N2	116.50 (12)
C6—C1—N3	123.98 (12)	C8—C13—N2	120.97 (12)
C2—C1—N3	116.18 (12)	N4—C14—N5	115.39 (11)
C3—C2—N4	126.71 (12)	N4—C14—S1	125.83 (11)
C3—C2—C1	118.81 (13)	N5—C14—S1	118.76 (10)
N4—C2—C1	114.48 (11)	C16—C15—C20	120.20 (14)
C4—C3—C2	120.16 (13)	C16—C15—N5	118.58 (13)
C4—C3—H3	119.9	C20—C15—N5	121.10 (15)
C2—C3—H3	119.9	C15—C16—C17	119.97 (15)
C3—C4—C5	120.97 (13)	C15—C16—H16	120.0
C3—C4—H4	119.5	C17—C16—H16	120.0
C5—C4—H4	119.5	C18—C17—C16	120.07 (18)
C4—C5—C6	119.67 (15)	C18—C17—H17	120.0
C4—C5—H5	120.2	C16—C17—H17	120.0
C6—C5—H5	120.2	C19—C18—C17	120.09 (15)
C5—C6—C1	120.30 (13)	C19—C18—H18	120.0
C5—C6—H6	119.9	C17—C18—H18	120.0
C1—C6—H6	119.9	C18—C19—C20	120.80 (17)
N3—C7—C8	120.17 (13)	C18—C19—H19	119.6
N3—C7—H7	119.9	C20—C19—H19	119.6
C8—C7—H7	119.9	C15—C20—C19	118.87 (18)
C9—C8—C13	116.94 (12)	C15—C20—H20	120.6
C9—C8—C7	119.16 (12)	C19—C20—H20	120.6
C13—C8—C7	123.75 (13)	O1—N1—O2	124.14 (13)
C10—C9—C8	121.91 (13)	O1—N1—C11	117.79 (14)
C10—C9—H9	119.0	O2—N1—C11	118.06 (14)
C8—C9—H9	119.0	O3—N2—O4	123.37 (15)
C11—C10—C9	118.42 (14)	O3—N2—C13	118.34 (13)
C11—C10—H10	120.8	O4—N2—C13	118.15 (13)
C9—C10—H10	120.8	C7—N3—C1	118.79 (12)
C12—C11—C10	122.65 (12)	C14—N4—C2	133.07 (11)
C12—C11—N1	118.55 (13)	C14—N4—H4A	113.5
C10—C11—N1	118.80 (14)	C2—N4—H4A	113.5
C11—C12—C13	117.43 (13)	C14—N5—C15	128.38 (12)
C11—C12—H12	121.3	C14—N5—H5A	115.8
C13—C12—H12	121.3	C15—N5—H5A	115.8
C12—C13—C8	122.50 (13)

C6—C1—C2—C3	6.0 (2)	N5—C15—C16—C17	−176.32 (14)
N3—C1—C2—C3	−175.84 (12)	C15—C16—C17—C18	−0.2 (2)
C6—C1—C2—N4	−173.89 (14)	C16—C17—C18—C19	0.3 (3)
N3—C1—C2—N4	4.25 (18)	C17—C18—C19—C20	−0.2 (3)
N4—C2—C3—C4	175.60 (15)	C16—C15—C20—C19	0.3 (3)
C1—C2—C3—C4	−4.3 (2)	N5—C15—C20—C19	176.38 (16)
C2—C3—C4—C5	−0.2 (3)	C18—C19—C20—C15	−0.1 (3)
C3—C4—C5—C6	3.0 (3)	C12—C11—N1—O1	−179.74 (16)
C4—C5—C6—C1	−1.2 (3)	C10—C11—N1—O1	−0.1 (2)
C2—C1—C6—C5	−3.3 (2)	C12—C11—N1—O2	0.8 (2)
N3—C1—C6—C5	178.69 (15)	C10—C11—N1—O2	−179.62 (15)
N3—C7—C8—C9	−20.9 (2)	C12—C13—N2—O3	−24.3 (2)
N3—C7—C8—C13	163.79 (13)	C8—C13—N2—O3	157.70 (17)
C13—C8—C9—C10	2.3 (2)	C12—C13—N2—O4	151.72 (17)
C7—C8—C9—C10	−173.30 (14)	C8—C13—N2—O4	−26.3 (2)
C8—C9—C10—C11	1.1 (2)	C8—C7—N3—C1	175.78 (12)
C9—C10—C11—C12	−2.8 (2)	C6—C1—N3—C7	−31.3 (2)
C9—C10—C11—N1	177.57 (13)	C2—C1—N3—C7	150.61 (13)
C10—C11—C12—C13	0.9 (2)	N5—C14—N4—C2	−175.70 (14)
N1—C11—C12—C13	−179.52 (12)	S1—C14—N4—C2	5.9 (2)
C11—C12—C13—C8	2.9 (2)	C3—C2—N4—C14	2.5 (2)
C11—C12—C13—N2	−175.14 (13)	C1—C2—N4—C14	−177.57 (14)
C9—C8—C13—C12	−4.4 (2)	N4—C14—N5—C15	5.2 (2)
C7—C8—C13—C12	171.00 (13)	S1—C14—N5—C15	−176.34 (13)
C9—C8—C13—N2	173.51 (13)	C16—C15—N5—C14	−121.98 (17)
C7—C8—C13—N2	−11.1 (2)	C20—C15—N5—C14	61.8 (2)
C20—C15—C16—C17	−0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3	0.86	2.14	2.614 (2)	114
C3—H3···S1	0.93	2.55	3.215 (2)	128
C7—H7···O4	0.93	2.34	2.749 (3)	106
N4—H4A···N3	0.86	2.14	2.614 (2)	114
N5—H5A···S1ⁱ	0.86	2.49	3.284 (2)	155
C12—H12···O3ⁱⁱ	0.93	2.57	3.397 (3)	148

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₅O₄S
M_r	421.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.362 (5), 18.767 (3), 12.379 (4)
β (°)	94.827 (5)
V (Å³)	1935.7 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.20 × 0.16 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.960, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	28336, 6878, 4509
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.752

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.02
No. of reflections	6878
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.37

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3	0.86	2.14	2.614 (2)	114
C3—H3···S1	0.93	2.55	3.215 (2)	128
C7—H7···O4	0.93	2.34	2.749 (3)	106
N4—H4A···N3	0.86	2.14	2.614 (2)	114
N5—H5A···S1ⁱ	0.86	2.49	3.284 (2)	155
C12—H12···O3ⁱⁱ	0.93	2.57	3.397 (3)	148

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

Acknowledgements

The authors wish to acknowledge IIT, Madras for the data collection.

References

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