1-[2-(2,4-Dinitro-benzyl-ideneamino)phen-yl]-3-phenyl-thio-urea.

In the title compound, C(20)H(15)N(5)O(4)S, the central benzene ring makes dihedral angles of 59.5 (1) and 51.7 (1)°, respectively, with the terminal phenyl and benzene rings. The mol-ecular structure exhibits weak intra-molecular N-H⋯N and C-H⋯S inter-actions. In the crystal structure, mol-ecules are linked by weak inter-molecular N-H⋯S and C-H⋯O inter-actions, forming a chain along [11].

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 = 421.43

Monoclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.137

S = 1.02

6878 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.37 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H15N5O4S	F(000) = 872
Mr = 421.43	Dx = 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

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

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(Fo2) + (0.0628P)2 + 0.3472P] where P = (Fo2 + 2Fc2)/3
6878 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .