Crystal structures of N-[(4-phenyl­thia­zol-2-yl)carbamo­thio­yl]benzamide and N-{[4-(4-bromo­phen­yl)thia­zol-2-yl]carbamo­thio­yl}benzamide from synchrotron X-ray diffraction

Gantimurova, E.S.; Bunev, A.S.; Talina, K.Y.; Ostapenko, G.I.; Dorovatovskii, P.V.; Lobanov, N.N.; Khrustalev, V.N.

doi:10.1107/S2056989016013396

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 72| Part 9| September 2016| Pages 1343-1347

https://doi.org/10.1107/S2056989016013396

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Crystal structures of N-[(4-phenylthiazol-2-yl)carbamothioyl]benzamide and N-{[4-(4-bromophenyl)thiazol-2-yl]carbamothioyl}benzamide from synchrotron X-ray diffraction

Ekaterina S. Gantimurova,^a Alexander S. Bunev,^a Kristina Yu. Talina,^a Gennady I. Ostapenko,^a Pavel V. Dorovatovskii,^b Nikolai N. Lobanov ^c and Victor N. Khrustalev ^c,^d ^*

^aLaboratory of Functional Heterocyclic Compounds, Togliatti State University, 14 Belorusskaya St., Togliatti 445020, Russian Federation, ^bNational Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation, ^cInorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow 117198, Russian Federation, and ^dX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: vnkhrustalev@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 August 2016; accepted 20 August 2016; online 26 August 2016)

The title compounds, C₁₇H₁₃N₃OS₂, (I), and C₁₇H₁₂BrN₃OS₂, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamothioyl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thiazole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thiazol-2-ylcarbamothioyl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromophenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intramolecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), molecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), molecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] interactions.

Keywords: crystal structure; thiourea; thiazoles; synchrotron; hydrogen bonds.

CCDC references: 1500238; 1500237

1. Chemical context

Thioureas are the subject of significant interest owing to their biological properties as fungicides, herbicides (Walpole et al., 1998 ) and rodenticides (Sarkis & Faisal, 1985 ). It is also well-known that thiourea derivatives and their metal complexes exhibit analgesic (El-Serwy et al., 2015 ), anti-inflammatory (Lin et al., 2013 ), antimicrobial (Stefanska et al., 2016 ) and anticancer (Rauf et al., 2015 ) activities. Moreover, thiourea derivatives are valuable building blocks for the synthesis of amides, guanidines and a variety of heterocycles (e.g. Kidwai et al., 2001 ; Du & Curran, 2003 ). Recently, thiourea derivatives were found to have use in organocatalysis (e.g. Connon, 2006 ; McCooey & Connon, 2005 ; Schreiner, 2003 ; Taylor & Jacobsen, 2006 ). For these reasons, a number of procedures have been reported for the synthesis of thioureas.

In this paper we report a synthetic approach for the preparation of the new thiourea derivatives (I) and (II) containing thiazole fragments, and their structural characterization by synchrotron single-crystal X-ray diffraction.

2. Structural commentary

Compound (I), C₁₇H₁₃N₃OS₂, comprises two almost planar fragments. The first is the central (carbamothioyl)amide grouping (r.m.s. deviation = 0.038 Å), and the second consists of the thiazole and two phenyl rings (r.m.s. deviation = 0.053 Å) (Fig. 1). The dihedral angle between these planes is 15.17 (5)°.

Figure 1
The molecular structure of (I)

. Displacement ellipsoids are shown at the 50% probability level. The dashed line indicates the intramolecular hydrogen bond. H atoms are presented as small spheres of arbitrary radius.

Unlike (I), compound (II), C₁₇H₁₂N₃OS₂Br, comprises three almost planar fragments: the first is the central N-(thiazol-2-ylcarbamothioyl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromophenyl and phenyl substituents, respectively (Fig. 2). The dihedral angles between the central and two terminal fragments are 21.58 (7) and 17.90 (9)°, respectively.

Figure 2
The molecular structure of (II)

. Displacement ellipsoids are shown at the 50% probability level. The dashed line indicates the intramolecular hydrogen bond. H atoms are presented as small spheres of arbitrary radius.

The planarity of the fragments found in (I) and (II) is determined by the present of bond conjugation within each of them as well as the intramolecular N1—H1⋯O1 hydrogen bond (Tables 1 and 2, Figs. 1 and 2). The different molecular conformations observed for (I) and (II) may apparently be explained by the various systems of intermolecular interactions present in the crystals (see the Supramolecular features section below).

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.92	1.85	2.6145 (18)	139
N2—H2⋯S1ⁱ	0.93	2.69	3.5845 (15)	162
C13—H13⋯O1ⁱⁱ	0.95	2.44	3.299 (2)	150
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.88	1.93	2.644 (3)	138
N2—H2⋯Br1ⁱ	0.88	2.97	3.692 (3)	141
C13—H13⋯O1ⁱⁱ	0.95	2.53	3.340 (4)	144
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

The bond-length and angle distribution within molecules (I) and (II) are almost identical and in good agreement with those observed in related compounds (Singh et al., 2012 , 2013 ). The values for the C—S—C angle in (I) [88.06 (8)°] and (II) [87.75 (14)°] are also very close to those in previously reported analogous structures [87.62 (7)–88.11 (8)°] (Yunus et al., 2008 ; Saeed et al., 2010 ).

3. Supramolecular features

Although the similarity of the molecular geometries and types of intramolecular hydrogen bonds might lead to similar packing motifs, this is not found in the case of (I) and (II). The intermolecular interactions, namely, N—H⋯X (X = S, Br) and C—H⋯O hydrogen bonding and the secondary S⋯S and S⋯Br interactions, combine in a different way, give rise to distinct packing motifs.

In (I), the crystal packing consists of hydrogen-bonded layers parallel to (100), in which the molecules are linked to each other by N2—H2⋯S1ⁱ and C13—H13⋯O1ⁱⁱ hydrogen bonds [Table 1, Fig. 3; symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ]. No secondary S⋯S intermolecular interactions were observed in (I).

Figure 3
The crystal structure of (I)

illustrating the hydrogen-bonded layers parallel to (100). Dashed lines indicate the intramolecular N—H⋯O and intermolecular N—H⋯S and C—H⋯O hydrogen bonds.

The situation in the case of (II) is quite different. The molecules of (II) form a three-dimensional framework mediated by the N2—H2⋯Br1ⁱ and C13—H13⋯O1ⁱⁱ hydrogen bonds (Table 2, Fig. 4) as well as the secondary S1⋯Br1ⁱⁱⁱ [3.3507 (11) Å] and S2⋯S2^iv [3.4343 (14) Å] interactions [symmetry codes: (i) x, −y + 1, z − $[{1\over 2}]$ ; (ii) −x + 1, −y, −z + 1; (iii) x, −y + 1, −z + 1; (iv) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ; Fig. 4]. It should be pointed out that the secondary intermolecular S⋯Br and S⋯S interactions in (II) are significantly stronger than the intermolecular hydrogen bonds and, consequently, structure-forming.

Figure 4
The crystal structure of (II)

. Dashed lines indicate the intramolecular N—H⋯O and intermolecular N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary intermolecular S⋯S and S⋯Br interactions.

4. Synthesis and crystallization

Benzoyl chloride (0.60 ml, 0.73 g, 5.19 mmol) was added over 5 min to a freshly prepared solution of NH₄SCN (0.39 g, 5.19 mmol) in acetone (40 ml), and the mixture was heated under reflux for 15 min. After heating, the appropriate 4-arylthiazol-2-amine (4.33 mmol) in acetone (10 ml) was added. The mixture was heated again under reflux for 2 h (Fig. 5). Then excess cracked ice was added with vigorous stirring. The resulting solid was collected and liberally washed with water. These compounds were isolated as pale-yellow crystalline solids in 41% and 45% yield for the 4-phenyl (I) and 4-(4-bromophenyl) (II) derivatives, respectively. Single crystals of the products were obtained by slow crystallization from N,N-dimethylformamide solution.

Figure 5
Synthesis of new thiourea derivatives (I)

and (II)

Spectroscopic and physical data for (I): m.p. 481–483 K. FTIR ν_max cm⁻¹: 3025, 1671, 1518, 1441, 1246, 1170, 668, 561. ¹H NMR (600 MHz, DMSO-d₆, 304 K): δ = 7.35 (t, 1H, J = 7.3), 7.45 (t, 2H, J = 7.6), 7.56 (t, 2H, J = 7.6), 7.69 (t, 1H, J = 7.4), 7.74 (s, 1H), 7.94 (d, 2H, J = 7.8), 8.03 (d, 2H, J = 7.8), 12.18 (s, 1H), 14.27 (s, 1H). Analysis calculated for C₁₇H₁₃N₃OS₂: C, 60.16; H, 3.86; N, 12.38. Found: C, 60.22; H, 3.93; N, 12.47.

Spectroscopic and physical data for (II): m.p. 484–486 K. FTIR ν_max cm⁻¹: 3395, 3055, 1674, 1515, 1488, 1244, 1165, 697. ¹H NMR (600 MHz, DMSO-d₆,304 K): δ = 7.57 (t, 2H, J = 7.7), 7.64 (d, 2H, J = 8.0), 7.70 (t, 1H, J = 7.5), 7.83 (s, 1H), 7.90 (d, 2H, J = 8.1), 8.03 (d, 2H, J = 7.7), 1221 (s, 1H), 14.27 (s, 1H). Analysis calculated for C₁₇H₁₂N₃OS₂Br: C, 48.81; H, 2.89; N, 10.05. Found: C, 48.89; H, 2.95; N, 10.11.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. X-ray diffraction studies were carried out on the `Belok' beamline (λ = 0.96990 Å) of the National Research Center `Kurchatov Institute' (Moscow, Russian Federation) using a MAR CCD detector. For each compound, a total of 360 images were collected using an oscillation range of 1.0° (φ scan mode) and corrected for absorption using the SCALA program (Evans, 2006 ). The data were indexed, integrated and scaled using the utility iMOSFLM in the program CCP4 (Battye et al., 2011 ).

Table 3
Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₇H₁₃N₃OS₂	C₁₇H₁₂BrN₃OS₂
M_r	339.42	418.33
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, C2/c
Temperature (K)	100	100
a, b, c (Å)	12.901 (3), 5.5160 (11), 23.143 (5)	37.210 (7), 4.0000 (8), 28.450 (6)
β (°)	105.32 (3)	128.69 (3)
V (Å³)	1588.4 (6)	3305.2 (18)
Z	4	8
Radiation type	Synchrotron, λ = 0.96990 Å	Synchrotron, λ = 0.96990 Å
μ (mm⁻¹)	0.81	1.56
Crystal size (mm)	0.15 × 0.10 × 0.05	0.07 × 0.05 × 0.03

Data collection
Diffractometer	MAR CCD	MAR CCD
Absorption correction	Multi-scan (SCALA; Evans, 2006)	Multi-scan (SCALA; Evans, 2006)
T_min, T_max	0.870, 0.950	0.880, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	26393, 3395, 2899	13698, 3267, 2523
R_int	0.033	0.065
(sin θ/λ)_max (Å⁻¹)	0.642	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.095, 1.03	0.040, 0.092, 1.02
No. of reflections	3395	3267
No. of parameters	209	217
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.32	0.62, −0.78
Computer programs: Automar (MarXperts, 2015 ), iMOSFLM (Battye et al., 2011), SHELXS97 and SHELXTL (Sheldrick, 2008 ) and SHELXL2014 (Sheldrick, 2015 ).

The hydrogen atoms of the amino groups were localized in the difference-Fourier map and included in the refinement with fixed positional (riding model) and isotropic displacement parameters [U_iso(H) = 1.2U_eq(N)]. The other hydrogen atoms were placed in calculated positions with C—H = 0.95 Å and refined using in a riding model with fixed isotropic displacement parameters [U_iso(H) = 1.2U_eq(C)].

Supporting information

CCDC references: 1500238; 1500237

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989016013396/hb7611sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016013396/hb7611Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016013396/hb7611IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016013396/hb7611Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989016013396/hb7611IIsup5.cml

checkCIF report

Computing details top

For both compounds, data collection: Automar (MarXperts, 2015); cell refinement: iMOSFLM (Battye et al., 2011); data reduction: iMOSFLM (Battye et al., 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) N-[(4-Phenylthiazol-2-yl)carbamothioyl]benzamide top

Crystal data top

C₁₇H₁₃N₃OS₂	F(000) = 704
M_r = 339.42	D_x = 1.419 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.96990 Å
a = 12.901 (3) Å	Cell parameters from 600 reflections
b = 5.5160 (11) Å	θ = 2.4–34.0°
c = 23.143 (5) Å	µ = 0.81 mm⁻¹
β = 105.32 (3)°	T = 100 K
V = 1588.4 (6) Å³	Prism, colourless
Z = 4	0.15 × 0.10 × 0.05 mm

Data collection top

MAR CCD diffractometer	2899 reflections with I > 2σ(I)
φ scan	R_int = 0.033
Absorption correction: multi-scan (SCALA; Evans, 2006)	θ_max = 38.5°, θ_min = 2.2°
T_min = 0.870, T_max = 0.950	h = −16→16
26393 measured reflections	k = −6→7
3395 independent reflections	l = −29→28

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0566P)² + 0.566P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3395 reflections	Δρ_max = 0.32 e Å⁻³
209 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.0035 (10)

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.

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

	x	y	z	U_iso*/U_eq
S1	0.41550 (3)	0.80075 (7)	0.45047 (2)	0.03118 (14)
S2	0.25885 (3)	1.09330 (7)	0.35070 (2)	0.02857 (14)
O1	0.47826 (9)	0.3167 (2)	0.30362 (5)	0.0333 (3)
N1	0.36884 (10)	0.6692 (2)	0.33491 (6)	0.0279 (3)
H1	0.3853	0.5686	0.3068	0.033*
N2	0.49953 (10)	0.4417 (2)	0.40077 (5)	0.0265 (3)
H2	0.5346	0.4048	0.4403	0.032*
N3	0.22879 (10)	0.8127 (2)	0.25771 (6)	0.0270 (3)
C1	0.42612 (12)	0.6327 (3)	0.39203 (7)	0.0262 (3)
C2	0.28765 (12)	0.8397 (3)	0.31264 (7)	0.0265 (3)
C3	0.15407 (12)	0.9994 (3)	0.24243 (7)	0.0266 (3)
C4	0.16011 (13)	1.1685 (3)	0.28659 (7)	0.0291 (3)
H4	0.1159	1.3086	0.2826	0.035*
C5	0.07557 (12)	0.9915 (3)	0.18273 (7)	0.0263 (3)
C6	0.07731 (13)	0.7958 (3)	0.14375 (7)	0.0292 (3)
H6	0.1300	0.6722	0.1555	0.035*
C7	0.00219 (13)	0.7826 (3)	0.08808 (8)	0.0342 (4)
H7	0.0038	0.6496	0.0623	0.041*
C8	−0.07530 (13)	0.9630 (3)	0.06996 (8)	0.0356 (4)
H8	−0.1264	0.9529	0.0320	0.043*
C9	−0.07725 (14)	1.1582 (3)	0.10782 (8)	0.0343 (4)
H9	−0.1298	1.2817	0.0956	0.041*
C10	−0.00247 (13)	1.1736 (3)	0.16369 (7)	0.0303 (4)
H10	−0.0043	1.3080	0.1891	0.036*
C11	0.52613 (12)	0.3002 (3)	0.35705 (7)	0.0268 (3)
C12	0.61647 (12)	0.1241 (3)	0.37854 (6)	0.0259 (3)
C13	0.62162 (12)	−0.0727 (3)	0.34049 (7)	0.0280 (3)
H13	0.5687	−0.0900	0.3034	0.034*
C14	0.70420 (13)	−0.2414 (3)	0.35736 (7)	0.0298 (3)
H14	0.7074	−0.3746	0.3319	0.036*
C15	0.78246 (13)	−0.2151 (3)	0.41177 (7)	0.0318 (4)
H15	0.8389	−0.3304	0.4232	0.038*
C16	0.77780 (13)	−0.0197 (3)	0.44932 (7)	0.0316 (4)
H16	0.8308	−0.0031	0.4864	0.038*
C17	0.69563 (12)	0.1514 (3)	0.43264 (7)	0.0282 (3)
H17	0.6934	0.2859	0.4579	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0401 (2)	0.0298 (2)	0.0231 (2)	0.00420 (17)	0.00737 (16)	−0.00296 (15)
S2	0.0325 (2)	0.0253 (2)	0.0282 (2)	0.00129 (15)	0.00863 (15)	−0.00300 (15)
O1	0.0376 (6)	0.0382 (7)	0.0228 (6)	0.0089 (5)	0.0059 (5)	−0.0010 (5)
N1	0.0319 (7)	0.0282 (7)	0.0236 (6)	0.0033 (6)	0.0075 (5)	−0.0021 (5)
N2	0.0288 (6)	0.0286 (7)	0.0214 (6)	0.0022 (5)	0.0056 (5)	0.0004 (5)
N3	0.0287 (6)	0.0259 (7)	0.0270 (7)	0.0016 (5)	0.0086 (5)	0.0007 (5)
C1	0.0271 (7)	0.0260 (8)	0.0264 (7)	−0.0013 (6)	0.0087 (6)	0.0004 (6)
C2	0.0300 (8)	0.0232 (8)	0.0282 (8)	0.0003 (6)	0.0110 (6)	0.0005 (6)
C3	0.0276 (7)	0.0231 (8)	0.0314 (8)	0.0003 (6)	0.0120 (6)	0.0024 (6)
C4	0.0301 (8)	0.0259 (8)	0.0318 (8)	0.0019 (6)	0.0089 (6)	0.0003 (6)
C5	0.0265 (7)	0.0239 (8)	0.0300 (8)	−0.0012 (6)	0.0103 (6)	0.0026 (6)
C6	0.0272 (7)	0.0254 (8)	0.0342 (8)	0.0016 (6)	0.0066 (6)	−0.0001 (6)
C7	0.0342 (9)	0.0286 (9)	0.0375 (9)	0.0005 (7)	0.0058 (7)	−0.0038 (7)
C8	0.0300 (8)	0.0388 (10)	0.0340 (8)	0.0002 (7)	0.0017 (7)	0.0012 (7)
C9	0.0330 (8)	0.0323 (9)	0.0377 (9)	0.0087 (7)	0.0098 (7)	0.0063 (7)
C10	0.0336 (8)	0.0270 (8)	0.0328 (8)	0.0053 (7)	0.0131 (7)	0.0019 (6)
C11	0.0282 (8)	0.0290 (8)	0.0234 (7)	−0.0012 (6)	0.0074 (6)	0.0001 (6)
C12	0.0274 (7)	0.0271 (8)	0.0243 (7)	−0.0009 (6)	0.0091 (6)	0.0011 (6)
C13	0.0291 (8)	0.0306 (8)	0.0252 (7)	−0.0022 (6)	0.0085 (6)	−0.0013 (6)
C14	0.0336 (8)	0.0287 (8)	0.0301 (8)	0.0000 (7)	0.0135 (6)	−0.0015 (6)
C15	0.0320 (8)	0.0309 (9)	0.0343 (9)	0.0065 (7)	0.0120 (7)	0.0050 (7)
C16	0.0290 (8)	0.0387 (10)	0.0259 (8)	0.0022 (7)	0.0053 (6)	0.0020 (7)
C17	0.0317 (8)	0.0287 (8)	0.0250 (8)	−0.0014 (7)	0.0089 (6)	−0.0011 (6)

Geometric parameters (Å, º) top

S1—C1	1.6747 (16)	C7—C8	1.394 (2)
S2—C4	1.7313 (17)	C7—H7	0.9500
S2—C2	1.7447 (16)	C8—C9	1.393 (3)
O1—C11	1.2308 (19)	C8—H8	0.9500
N1—C1	1.348 (2)	C9—C10	1.397 (2)
N1—C2	1.401 (2)	C9—H9	0.9500
N1—H1	0.9210	C10—H10	0.9500
N2—C11	1.3909 (19)	C11—C12	1.498 (2)
N2—C1	1.395 (2)	C12—C17	1.399 (2)
N2—H2	0.9300	C12—C13	1.410 (2)
N3—C2	1.306 (2)	C13—C14	1.391 (2)
N3—C3	1.391 (2)	C13—H13	0.9500
C3—C4	1.371 (2)	C14—C15	1.398 (2)
C3—C5	1.482 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.396 (2)
C5—C10	1.408 (2)	C15—H15	0.9500
C5—C6	1.411 (2)	C16—C17	1.395 (2)
C6—C7	1.395 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500

C4—S2—C2	88.06 (8)	C9—C8—H8	120.2
C1—N1—C2	128.58 (13)	C7—C8—H8	120.2
C1—N1—H1	115.7	C8—C9—C10	120.43 (15)
C2—N1—H1	115.7	C8—C9—H9	119.8
C11—N2—C1	127.36 (13)	C10—C9—H9	119.8
C11—N2—H2	116.3	C9—C10—C5	120.55 (15)
C1—N2—H2	116.3	C9—C10—H10	119.7
C2—N3—C3	110.42 (13)	C5—C10—H10	119.7
N1—C1—N2	115.46 (13)	O1—C11—N2	122.31 (14)
N1—C1—S1	124.67 (12)	O1—C11—C12	121.44 (14)
N2—C1—S1	119.87 (11)	N2—C11—C12	116.25 (13)
N3—C2—N1	117.88 (14)	C17—C12—C13	119.85 (14)
N3—C2—S2	115.87 (12)	C17—C12—C11	123.20 (14)
N1—C2—S2	126.22 (12)	C13—C12—C11	116.92 (13)
C4—C3—N3	114.53 (14)	C14—C13—C12	119.92 (14)
C4—C3—C5	127.25 (14)	C14—C13—H13	120.0
N3—C3—C5	118.17 (14)	C12—C13—H13	120.0
C3—C4—S2	111.10 (12)	C13—C14—C15	120.06 (15)
C3—C4—H4	124.5	C13—C14—H14	120.0
S2—C4—H4	124.5	C15—C14—H14	120.0
C10—C5—C6	118.47 (15)	C16—C15—C14	120.09 (15)
C10—C5—C3	121.79 (14)	C16—C15—H15	120.0
C6—C5—C3	119.73 (14)	C14—C15—H15	120.0
C7—C6—C5	120.38 (15)	C15—C16—C17	120.29 (15)
C7—C6—H6	119.8	C15—C16—H16	119.9
C5—C6—H6	119.8	C17—C16—H16	119.9
C8—C7—C6	120.58 (16)	C16—C17—C12	119.77 (15)
C8—C7—H7	119.7	C16—C17—H17	120.1
C6—C7—H7	119.7	C12—C17—H17	120.1
C9—C8—C7	119.56 (16)

C2—N1—C1—N2	177.74 (14)	C5—C6—C7—C8	0.3 (3)
C2—N1—C1—S1	−3.2 (2)	C6—C7—C8—C9	0.2 (3)
C11—N2—C1—N1	5.9 (2)	C7—C8—C9—C10	−0.2 (3)
C11—N2—C1—S1	−173.23 (12)	C8—C9—C10—C5	−0.4 (2)
C3—N3—C2—N1	−178.70 (13)	C6—C5—C10—C9	0.9 (2)
C3—N3—C2—S2	−0.34 (17)	C3—C5—C10—C9	−178.30 (14)
C1—N1—C2—N3	−166.94 (15)	C1—N2—C11—O1	−6.7 (2)
C1—N1—C2—S2	14.9 (2)	C1—N2—C11—C12	173.58 (14)
C4—S2—C2—N3	−0.53 (12)	O1—C11—C12—C17	157.43 (15)
C4—S2—C2—N1	177.67 (14)	N2—C11—C12—C17	−22.9 (2)
C2—N3—C3—C4	1.36 (19)	O1—C11—C12—C13	−20.5 (2)
C2—N3—C3—C5	−176.47 (13)	N2—C11—C12—C13	159.15 (13)
N3—C3—C4—S2	−1.76 (17)	C17—C12—C13—C14	1.2 (2)
C5—C3—C4—S2	175.84 (12)	C11—C12—C13—C14	179.22 (13)
C2—S2—C4—C3	1.25 (12)	C12—C13—C14—C15	−0.5 (2)
C4—C3—C5—C10	2.7 (2)	C13—C14—C15—C16	0.1 (2)
N3—C3—C5—C10	−179.82 (13)	C14—C15—C16—C17	−0.5 (2)
C4—C3—C5—C6	−176.52 (15)	C15—C16—C17—C12	1.2 (2)
N3—C3—C5—C6	1.0 (2)	C13—C12—C17—C16	−1.6 (2)
C10—C5—C6—C7	−0.9 (2)	C11—C12—C17—C16	−179.47 (14)
C3—C5—C6—C7	178.33 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.92	1.85	2.6145 (18)	139
N2—H2···S1ⁱ	0.93	2.69	3.5845 (15)	162
C13—H13···O1ⁱⁱ	0.95	2.44	3.299 (2)	150

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

(II) N-{[4-(4-Bromophenyl)thiazol-2-yl]carbamothioyl}benzamide top

Crystal data top

C₁₇H₁₂BrN₃OS₂	F(000) = 1680
M_r = 418.33	D_x = 1.681 Mg m⁻³
Monoclinic, C2/c	Synchrotron radiation, λ = 0.96990 Å
a = 37.210 (7) Å	Cell parameters from 500 reflections
b = 4.0000 (8) Å	θ = 4.0–33.0°
c = 28.450 (6) Å	µ = 1.56 mm⁻¹
β = 128.69 (3)°	T = 100 K
V = 3305.2 (18) Å³	Prism, colourless
Z = 8	0.07 × 0.05 × 0.03 mm

Data collection top

MAR CCD diffractometer	2523 reflections with I > 2σ(I)
φ scan	R_int = 0.065
Absorption correction: multi-scan (SCALA; Evans, 2006)	θ_max = 38.4°, θ_min = 4.0°
T_min = 0.880, T_max = 0.930	h = −44→44
13698 measured reflections	k = −4→4
3267 independent reflections	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.02P)²] where P = (F_o² + 2F_c²)/3
3267 reflections	(Δ/σ)_max = 0.002
217 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
Br1	0.66455 (2)	0.24056 (7)	0.96731 (2)	0.02282 (14)
S1	0.67189 (2)	0.95707 (16)	0.58750 (3)	0.02136 (19)
S2	0.70200 (2)	0.97423 (15)	0.71326 (3)	0.01827 (18)
O1	0.55011 (6)	0.3045 (5)	0.53088 (9)	0.0239 (5)
N1	0.62216 (7)	0.6652 (5)	0.61537 (10)	0.0176 (5)
H1	0.5969	0.5551	0.6017	0.021*
N2	0.59498 (7)	0.6073 (5)	0.51692 (9)	0.0194 (5)
H2	0.5969	0.6736	0.4890	0.023*
N3	0.64079 (7)	0.6390 (5)	0.71031 (9)	0.0178 (5)
C1	0.62849 (9)	0.7359 (6)	0.57480 (13)	0.0183 (7)
C2	0.65111 (9)	0.7460 (6)	0.67684 (13)	0.0173 (6)
C3	0.67476 (9)	0.7355 (6)	0.76996 (13)	0.0167 (6)
C4	0.70985 (8)	0.9180 (6)	0.77919 (12)	0.0197 (6)
H4	0.7353	1.0029	0.8172	0.024*
C5	0.67149 (8)	0.6265 (6)	0.81672 (11)	0.0175 (6)
C6	0.71033 (9)	0.6346 (7)	0.87798 (12)	0.0213 (6)
H6	0.7387	0.7176	0.8894	0.026*
C7	0.70779 (8)	0.5233 (6)	0.92191 (12)	0.0219 (7)
H7	0.7343	0.5286	0.9631	0.026*
C8	0.66619 (8)	0.4035 (6)	0.90546 (12)	0.0193 (6)
C9	0.62698 (9)	0.3949 (7)	0.84512 (12)	0.0223 (6)
H9	0.5986	0.3141	0.8340	0.027*
C10	0.63006 (9)	0.5062 (6)	0.80154 (12)	0.0216 (6)
H10	0.6034	0.5006	0.7604	0.026*
C11	0.55924 (8)	0.3889 (6)	0.49790 (12)	0.0187 (6)
C12	0.53267 (9)	0.2627 (6)	0.43455 (13)	0.0184 (7)
C13	0.48960 (8)	0.1152 (7)	0.40853 (12)	0.0216 (6)
H13	0.4785	0.1002	0.4308	0.026*
C14	0.46331 (9)	−0.0089 (6)	0.34991 (12)	0.0239 (7)
H14	0.4341	−0.1062	0.3321	0.029*
C15	0.47950 (9)	0.0089 (6)	0.31750 (13)	0.0253 (7)
H15	0.4613	−0.0754	0.2775	0.030*
C16	0.52255 (9)	0.1505 (7)	0.34332 (13)	0.0262 (7)
H16	0.5337	0.1612	0.3210	0.031*
C17	0.54912 (9)	0.2757 (6)	0.40176 (13)	0.0225 (7)
H17	0.5785	0.3702	0.4194	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0213 (2)	0.0297 (2)	0.0189 (2)	0.00396 (11)	0.01329 (17)	0.00383 (11)
S1	0.0214 (3)	0.0250 (3)	0.0184 (4)	−0.0048 (3)	0.0128 (3)	−0.0023 (3)
S2	0.0148 (3)	0.0215 (3)	0.0161 (4)	−0.0005 (2)	0.0085 (3)	−0.0005 (2)
O1	0.0196 (10)	0.0343 (11)	0.0182 (11)	−0.0039 (8)	0.0119 (9)	0.0011 (8)
N1	0.0130 (10)	0.0241 (11)	0.0136 (12)	−0.0010 (8)	0.0073 (10)	0.0011 (9)
N2	0.0181 (10)	0.0249 (12)	0.0119 (11)	−0.0010 (9)	0.0078 (9)	0.0018 (9)
N3	0.0145 (10)	0.0206 (11)	0.0136 (11)	0.0014 (9)	0.0066 (9)	0.0006 (9)
C1	0.0154 (13)	0.0199 (13)	0.0149 (15)	0.0050 (9)	0.0072 (12)	0.0032 (9)
C2	0.0154 (13)	0.0217 (14)	0.0132 (14)	0.0026 (9)	0.0082 (12)	0.0013 (9)
C3	0.0144 (13)	0.0169 (13)	0.0156 (15)	0.0024 (9)	0.0079 (12)	−0.0009 (9)
C4	0.0179 (12)	0.0214 (13)	0.0144 (14)	0.0000 (10)	0.0075 (11)	−0.0006 (10)
C5	0.0171 (12)	0.0196 (12)	0.0132 (13)	0.0035 (10)	0.0083 (11)	0.0004 (10)
C6	0.0141 (12)	0.0292 (14)	0.0185 (15)	0.0000 (11)	0.0091 (12)	0.0000 (11)
C7	0.0141 (12)	0.0308 (15)	0.0129 (14)	0.0024 (10)	0.0046 (11)	−0.0020 (10)
C8	0.0187 (12)	0.0231 (13)	0.0160 (14)	0.0038 (10)	0.0108 (11)	0.0004 (10)
C9	0.0186 (13)	0.0268 (14)	0.0211 (15)	−0.0028 (11)	0.0122 (12)	−0.0021 (11)
C10	0.0169 (12)	0.0291 (14)	0.0146 (14)	0.0000 (10)	0.0078 (11)	−0.0017 (10)
C11	0.0131 (12)	0.0221 (13)	0.0142 (14)	0.0019 (10)	0.0054 (11)	0.0031 (10)
C12	0.0135 (13)	0.0212 (14)	0.0144 (15)	0.0023 (9)	0.0057 (12)	0.0015 (9)
C13	0.0174 (13)	0.0244 (14)	0.0193 (15)	0.0022 (11)	0.0097 (12)	0.0018 (11)
C14	0.0148 (13)	0.0256 (14)	0.0218 (15)	−0.0017 (10)	0.0068 (12)	−0.0014 (11)
C15	0.0212 (13)	0.0269 (15)	0.0161 (14)	0.0000 (10)	0.0059 (12)	−0.0025 (11)
C16	0.0268 (15)	0.0312 (15)	0.0199 (15)	−0.0015 (12)	0.0142 (13)	−0.0025 (12)
C17	0.0153 (13)	0.0269 (15)	0.0186 (16)	−0.0029 (10)	0.0073 (13)	−0.0004 (10)

Geometric parameters (Å, º) top

Br1—C8	1.913 (3)	C6—H6	0.9500
S1—C1	1.670 (3)	C7—C8	1.393 (4)
S2—C4	1.723 (3)	C7—H7	0.9500
S2—C2	1.743 (3)	C8—C9	1.395 (4)
O1—C11	1.228 (4)	C9—C10	1.388 (4)
N1—C1	1.345 (4)	C9—H9	0.9500
N1—C2	1.403 (4)	C10—H10	0.9500
N1—H1	0.8800	C11—C12	1.501 (4)
N2—C11	1.387 (3)	C12—C17	1.401 (5)
N2—C1	1.401 (3)	C12—C13	1.408 (4)
N2—H2	0.8800	C13—C14	1.394 (4)
N3—C2	1.302 (4)	C13—H13	0.9500
N3—C3	1.394 (3)	C14—C15	1.383 (4)
C3—C4	1.370 (4)	C14—H14	0.9500
C3—C5	1.476 (4)	C15—C16	1.398 (4)
C4—H4	0.9500	C15—H15	0.9500
C5—C10	1.401 (4)	C16—C17	1.392 (4)
C5—C6	1.407 (3)	C16—H16	0.9500
C6—C7	1.385 (4)	C17—H17	0.9500

C4—S2—C2	87.75 (14)	C7—C8—Br1	118.4 (2)
C1—N1—C2	127.7 (2)	C9—C8—Br1	120.9 (2)
C1—N1—H1	116.1	C10—C9—C8	119.0 (3)
C2—N1—H1	116.1	C10—C9—H9	120.5
C11—N2—C1	128.4 (3)	C8—C9—H9	120.5
C11—N2—H2	115.8	C9—C10—C5	121.6 (2)
C1—N2—H2	115.8	C9—C10—H10	119.2
C2—N3—C3	110.0 (2)	C5—C10—H10	119.2
N1—C1—N2	115.3 (2)	O1—C11—N2	122.0 (3)
N1—C1—S1	126.2 (2)	O1—C11—C12	122.4 (2)
N2—C1—S1	118.6 (2)	N2—C11—C12	115.6 (3)
N3—C2—N1	119.2 (2)	C17—C12—C13	119.6 (3)
N3—C2—S2	116.4 (2)	C17—C12—C11	123.6 (2)
N1—C2—S2	124.3 (2)	C13—C12—C11	116.8 (3)
C4—C3—N3	114.3 (3)	C14—C13—C12	119.7 (3)
C4—C3—C5	126.2 (2)	C14—C13—H13	120.2
N3—C3—C5	119.5 (2)	C12—C13—H13	120.2
C3—C4—S2	111.6 (2)	C15—C14—C13	120.4 (3)
C3—C4—H4	124.2	C15—C14—H14	119.8
S2—C4—H4	124.2	C13—C14—H14	119.8
C10—C5—C6	118.1 (3)	C14—C15—C16	120.3 (3)
C10—C5—C3	121.2 (2)	C14—C15—H15	119.9
C6—C5—C3	120.7 (2)	C16—C15—H15	119.9
C7—C6—C5	120.9 (3)	C17—C16—C15	119.9 (3)
C7—C6—H6	119.5	C17—C16—H16	120.1
C5—C6—H6	119.5	C15—C16—H16	120.1
C6—C7—C8	119.7 (2)	C16—C17—C12	120.2 (3)
C6—C7—H7	120.1	C16—C17—H17	119.9
C8—C7—H7	120.1	C12—C17—H17	119.9
C7—C8—C9	120.7 (3)

C2—N1—C1—N2	176.6 (2)	C6—C7—C8—C9	−0.1 (4)
C2—N1—C1—S1	−3.2 (4)	C6—C7—C8—Br1	178.3 (2)
C11—N2—C1—N1	−7.5 (4)	C7—C8—C9—C10	0.3 (4)
C11—N2—C1—S1	172.2 (2)	Br1—C8—C9—C10	−178.0 (2)
C3—N3—C2—N1	177.7 (2)	C8—C9—C10—C5	0.0 (4)
C3—N3—C2—S2	−0.5 (3)	C6—C5—C10—C9	−0.5 (4)
C1—N1—C2—N3	−175.8 (2)	C3—C5—C10—C9	178.3 (2)
C1—N1—C2—S2	2.2 (4)	C1—N2—C11—O1	7.4 (4)
C4—S2—C2—N3	0.2 (2)	C1—N2—C11—C12	−172.4 (2)
C4—S2—C2—N1	−177.9 (2)	O1—C11—C12—C17	−161.6 (2)
C2—N3—C3—C4	0.6 (3)	N2—C11—C12—C17	18.2 (3)
C2—N3—C3—C5	−176.9 (2)	O1—C11—C12—C13	16.4 (4)
N3—C3—C4—S2	−0.5 (3)	N2—C11—C12—C13	−163.8 (2)
C5—C3—C4—S2	176.8 (2)	C17—C12—C13—C14	−1.6 (4)
C2—S2—C4—C3	0.17 (19)	C11—C12—C13—C14	−179.6 (2)
C4—C3—C5—C10	165.8 (2)	C12—C13—C14—C15	0.7 (4)
N3—C3—C5—C10	−17.0 (4)	C13—C14—C15—C16	0.3 (4)
C4—C3—C5—C6	−15.5 (4)	C14—C15—C16—C17	−0.4 (4)
N3—C3—C5—C6	161.7 (2)	C15—C16—C17—C12	−0.5 (4)
C10—C5—C6—C7	0.7 (4)	C13—C12—C17—C16	1.5 (4)
C3—C5—C6—C7	−178.1 (2)	C11—C12—C17—C16	179.4 (2)
C5—C6—C7—C8	−0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.93	2.644 (3)	138
N2—H2···Br1ⁱ	0.88	2.97	3.692 (3)	141
C13—H13···O1ⁱⁱ	0.95	2.53	3.340 (4)	144

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

Acknowledgements

This work was supported financially by the Ministry of Education and Science of the Russian Federation in the program to improve the competitiveness of the Peoples' Friendship University of Russia (RUDN University) among the world's leading research and education centers in 2016–2020 and in the framework of State program No. 426.

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ISSN: 2056-9890

Volume 72| Part 9| September 2016| Pages 1343-1347

https://doi.org/10.1107/S2056989016013396

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of N-[(4-phenyl­thia­zol-2-yl)carbamo­thio­yl]benzamide and N-{[4-(4-bromo­phen­yl)thia­zol-2-yl]carbamo­thio­yl}benzamide from synchrotron X-ray diffraction

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Synthesis and crystallization

5. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structures of N-[(4-phenylthiazol-2-yl)carbamothioyl]benzamide and N-{[4-(4-bromophenyl)thiazol-2-yl]carbamothioyl}benzamide from synchrotron X-ray diffraction

3. Supramolecular features