(R)-1-(4-Bromo­benzo­yl)-4-(1-phenyl­prop­yl)thio­semicarbazide

Serwer, M.; Khawar Rauf, M.; Ebihara, M.; Hameed, S.

doi:10.1107/S1600536808006806

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o812

doi:10.1107/S1600536808006806

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(R)-1-(4-Bromobenzoyl)-4-(1-phenylpropyl)thiosemicarbazide

Monazza Serwer,^a M. Khawar Rauf,^b Masahiro Ebihara ^b and Shahid Hameed ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
^*Correspondence e-mail: shameed@qau.edu.pk

(Received 9 March 2008; accepted 11 March 2008; online 10 April 2008)

The title compound, C₁₇H₁₈BrN₃OS, is an important intermediate for the synthesis of biologically active heterocyclic compounds. The thiourea group is approximately planar. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen-bonding interactions.

Related literature

For related literature, see: Akhtar et al. (2006 , 2007 ); Cardia et al. (2006 ); Dolman et al. (2006 ); Hassan et al. (2006 ); Jalilian et al. (2000 ); Kucukguzel et al. (2006 ); Mohareb et al. (2007 ); Singh et al. (2003 , 2005 ).

Experimental

Crystal data

C₁₇H₁₈BrN₃OS
M_r = 392.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.263 (3) Å
b = 9.698 (5) Å
c = 27.651 (15) Å
V = 1679.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.58 mm⁻¹
T = 123 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: integration (NUMABS; Higashi, 1999 ) T_min = 0.512, T_max = 0.626
13732 measured reflections
3824 independent reflections
3516 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.074
S = 1.13
3824 reflections
219 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 1584 Friedel pairs
Flack parameter: 0.020 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.84 (4)	2.03 (4)	2.834 (4)	161 (4)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006806/hg2385sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006806/hg2385Isup2.hkl

checkCIF report

Comment top

Thiosemicarbazides have attracted much attention partly because of their biological activities such as antifungal (Mohareb et al., 2007), antibacterial (Kucukguzel et al., 2006), antiamoebic (Singh et al., 2005) antitubercular (Cardia et al.,2006), corrosion inhibitors (Singh et al., 2003) and partly because of their use as intermediates in the synthesis of many biologically active heterocyclic compounds like 1,3,4-oxadiazoles (Dolman et al., 2006), 1,3,4-thiadiazoles (Jalilian et al.,2000) and 1,2,4-triazole (Akhtar et al., 2007; Akhtar et al., 2006). The other important biologically active compounds synthesized from thiosemicarbazides include thiazoles, thiazines, thiadiazines, pyrazines and indazoles (Hassan et al., 2006). The C2—S1 and C1—O1 bonds both show the expected full double-bond character, while the short values for the C1—N1, C2—N2, N1—N2,C2—N3 and C9—N3 bond lengths also indicate partial double-bond character. The thiourea group is approximately planar. The crystal packing is stabilized by N(1)—H(1)···O(1) and N(3)—H(3)···S(1) hydrogen bonds.

Related literature top

For related literature, see: Akhtar et al. (2006, 2007); Cardia et al. (2006); Dolman et al. (2006); Hassan et al. (2006); Jalilian et al. (2000); Kucukguzel et al. (2006); Mohareb et al. (2007); Singh et al. (2003, 2005).

Experimental top

The 4-bromobenzoic acid hydrazide (0.0068 moles) was dissolved in methanol (30ml) and a solution of 0.0066 moles of R-(+)-1-phenylpropylisothiocyanate, separately dissolved in 10 ml of methanol, was added drop wise with continuous stirring. The reaction mixture was refluxed and after consumption of the starting materials (tlc), the mixture was cooled to room temperature and methanol evaporated in vacuo. The crude thiosemicarbazide was recrystallized from a mixture of ethyl acetate and petroleum ether. Yield: 85%; m.p 160-161 °C; R_f: 0.34 (Petroleum ether: acetone; 6:4); IR (ν_max, KBr, cm^-1): 3378, 3273, 3191, 3033, 2967, 2877, 1669, 1238, 1591, 1528, 699; ¹H-NMR (Acetone-d₆): δ 9.81 (1H, s), 8.58 (1H, s), 8.06 (1H, s), 0.97 (3H, t, J = 7.5 Hz), 1.92-1.82 (2H, m), 5.58 (1H, dd, J = 15.6, 7.2 Hz), 7.39 (2H, dd, J = 7.2, 1.5 Hz ), 7.30 (2H, dt, J = 7.5, 3.0 Hz), 7.22 (1H, dt, J = 7.2, 3.0 Hz), 7.92 (2H, d, J = 8.4 Hz), 7.72 (2H, d, J = 8.7 Hz); ¹³C-NMR (Acetone-d₆):δ 183.51, 165.60, 142.88, 133.20, 131.64, 129.61, 128.10, 126.87, 126.74,126.12, 59.55, 28.21, 10.47; EIMS: (m/z %) 214 (20), 183 (100), 155 (55),104 (10), 76 (50), 50 (45). Elemental analysis for C₁₇H₁₈N₃SOBr (391):C, 52.05; H, 4.62; N, 10.71; S, 8.17. Found: C, 51.96; H, 4.70; N, 10.82; S, 8.07.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. Showing hydrogen bonded molecules through N—H···O.

(R)-1-(4-Bromobenzoyl)-4-(1-phenylpropyl)thiosemicarbazide top

Crystal data top

C₁₇H₁₈BrN₃OS	F(000) = 800
M_r = 392.31	D_x = 1.552 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4820 reflections
a = 6.263 (3) Å	θ = 3.1–27.5°
b = 9.698 (5) Å	µ = 2.58 mm⁻¹
c = 27.651 (15) Å	T = 123 K
V = 1679.5 (15) Å³	Block, colourles
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3516 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: integration (NUMABS; Higashi, 1999)	h = −8→8
T_min = 0.512, T_max = 0.627	k = −12→8
13732 measured reflections	l = −26→35

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + 1.3691P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.074	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.34 e Å⁻³
3824 reflections	Δρ_min = −0.35 e Å⁻³
219 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0018 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1584 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.020 (10)

Crystal data top

C₁₇H₁₈BrN₃OS	V = 1679.5 (15) Å³
M_r = 392.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.263 (3) Å	µ = 2.58 mm⁻¹
b = 9.698 (5) Å	T = 123 K
c = 27.651 (15) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Rigaku/MSC Mercury CCD diffractometer	3824 independent reflections
Absorption correction: integration (NUMABS; Higashi, 1999)	3516 reflections with I > 2σ(I)
T_min = 0.512, T_max = 0.627	R_int = 0.057
13732 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.074	Δρ_max = 0.34 e Å⁻³
S = 1.13	Δρ_min = −0.35 e Å⁻³
3824 reflections	Absolute structure: Flack (1983), 1584 Friedel pairs
219 parameters	Absolute structure parameter: 0.020 (10)
0 restraints

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
C1	0.0742 (6)	0.2098 (3)	0.24009 (12)	0.0141 (8)
O1	0.0089 (4)	0.0922 (2)	0.23367 (10)	0.0260 (7)
N1	−0.0306 (5)	0.3005 (3)	0.26956 (12)	0.0144 (7)
H1	0.006 (6)	0.384 (4)	0.2666 (13)	0.017*
C2	−0.2924 (6)	0.2804 (3)	0.33209 (13)	0.0124 (8)
S1	−0.55059 (15)	0.30911 (9)	0.34643 (4)	0.0169 (2)
N2	−0.2383 (5)	0.2701 (3)	0.28467 (12)	0.0144 (7)
H2	−0.319 (7)	0.288 (4)	0.2668 (15)	0.017*
N3	−0.1369 (5)	0.2639 (3)	0.36436 (12)	0.0146 (6)
H3	−0.024 (6)	0.254 (3)	0.3547 (15)	0.017*
C3	0.2725 (6)	0.2613 (3)	0.21649 (13)	0.0134 (8)
C4	0.3408 (6)	0.3985 (4)	0.21787 (13)	0.0156 (8)
H4	0.2625	0.4643	0.2361	0.019*
C5	0.5216 (6)	0.4390 (3)	0.19285 (14)	0.0171 (8)
H5	0.5681	0.5322	0.1939	0.020*
C6	0.6334 (7)	0.3426 (3)	0.16636 (12)	0.0153 (7)
C7	0.5710 (6)	0.2056 (4)	0.16486 (13)	0.0197 (8)
H7	0.6508	0.1401	0.1468	0.024*
C8	0.3915 (7)	0.1659 (3)	0.18998 (13)	0.0169 (8)
H8	0.3479	0.0721	0.1893	0.020*
Br1	0.87772 (7)	0.39971 (4)	0.131114 (15)	0.02482 (12)
C9	−0.1593 (6)	0.2802 (3)	0.41665 (12)	0.0152 (8)
H9	−0.3033	0.3217	0.4224	0.018*
C10	−0.1581 (6)	0.1398 (3)	0.44199 (13)	0.0154 (8)
C11	−0.3136 (6)	0.0440 (3)	0.42905 (14)	0.0207 (9)
H11	−0.4171	0.0674	0.4053	0.025*
C12	−0.3188 (7)	−0.0852 (4)	0.45040 (15)	0.0258 (10)
H12	−0.4244	−0.1503	0.4410	0.031*
C13	−0.1711 (7)	−0.1193 (4)	0.48521 (14)	0.0273 (10)
H13	−0.1748	−0.2078	0.4999	0.033*
C14	−0.0166 (7)	−0.0245 (4)	0.49888 (16)	0.0305 (11)
H14	0.0848	−0.0475	0.5231	0.037*
C15	−0.0110 (6)	0.1039 (4)	0.47705 (14)	0.0231 (9)
H15	0.0956	0.1683	0.4863	0.028*
C16	0.0052 (6)	0.3842 (4)	0.43521 (13)	0.0200 (8)
H16A	0.1506	0.3475	0.4296	0.024*
H16B	−0.0137	0.3966	0.4705	0.024*
C17	−0.0165 (7)	0.5243 (4)	0.41003 (15)	0.0276 (10)
H17A	0.0209	0.5147	0.3758	0.041*
H17B	0.0798	0.5909	0.4254	0.041*
H17C	−0.1641	0.5569	0.4129	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.017 (2)	0.0147 (16)	0.0109 (19)	0.0004 (14)	0.0000 (16)	0.0045 (13)
O1	0.0226 (16)	0.0156 (12)	0.0397 (18)	−0.0052 (12)	0.0131 (13)	−0.0043 (12)
N1	0.0114 (16)	0.0133 (13)	0.0185 (19)	−0.0054 (12)	0.0049 (14)	0.0010 (12)
C2	0.0131 (19)	0.0096 (15)	0.015 (2)	−0.0006 (13)	0.0013 (16)	−0.0013 (13)
S1	0.0102 (5)	0.0220 (4)	0.0184 (5)	0.0014 (4)	0.0029 (4)	0.0007 (4)
N2	0.0078 (17)	0.0215 (16)	0.0140 (19)	−0.0001 (13)	−0.0027 (14)	0.0057 (13)
N3	0.0102 (15)	0.0230 (13)	0.0105 (16)	0.0013 (12)	0.0013 (17)	−0.0019 (12)
C3	0.0120 (19)	0.0140 (16)	0.014 (2)	0.0009 (13)	−0.0015 (16)	0.0044 (13)
C4	0.015 (2)	0.0156 (15)	0.0165 (19)	0.0032 (17)	0.0005 (16)	0.0038 (15)
C5	0.018 (2)	0.0155 (17)	0.018 (2)	−0.0002 (14)	−0.0004 (18)	0.0023 (14)
C6	0.0116 (18)	0.0256 (16)	0.0087 (18)	0.0002 (15)	0.0002 (18)	0.0040 (13)
C7	0.020 (2)	0.0242 (17)	0.015 (2)	0.0037 (15)	0.0044 (17)	−0.0027 (15)
C8	0.016 (2)	0.0158 (15)	0.019 (2)	−0.0009 (15)	0.0043 (19)	0.0004 (13)
Br1	0.01688 (19)	0.03197 (19)	0.0256 (2)	−0.00092 (17)	0.0097 (2)	0.00672 (18)
C9	0.015 (2)	0.0230 (17)	0.0078 (19)	−0.0003 (15)	0.0031 (16)	−0.0007 (13)
C10	0.018 (2)	0.0194 (16)	0.0090 (18)	0.0018 (14)	0.0014 (17)	−0.0006 (12)
C11	0.020 (2)	0.0270 (18)	0.015 (2)	−0.0036 (15)	−0.0038 (17)	0.0045 (15)
C12	0.028 (3)	0.028 (2)	0.021 (2)	−0.0071 (18)	0.0013 (18)	−0.0019 (17)
C13	0.038 (3)	0.0230 (19)	0.021 (2)	0.0071 (18)	0.005 (2)	0.0009 (16)
C14	0.035 (3)	0.033 (2)	0.023 (3)	0.0116 (19)	−0.011 (2)	0.0005 (18)
C15	0.027 (2)	0.0242 (18)	0.018 (2)	−0.0021 (19)	−0.0045 (18)	0.0018 (18)
C16	0.020 (2)	0.0275 (18)	0.013 (2)	−0.0051 (16)	0.0007 (16)	−0.0030 (16)
C17	0.032 (3)	0.030 (2)	0.021 (2)	−0.0109 (18)	0.004 (2)	0.0027 (17)

Geometric parameters (Å, º) top

C1—O1	1.224 (4)	C8—H8	0.9500
C1—N1	1.367 (4)	C9—C16	1.531 (5)
C1—C3	1.489 (5)	C9—C10	1.532 (4)
N1—N2	1.397 (4)	C9—H9	1.0000
N1—H1	0.84 (4)	C10—C15	1.382 (5)
C2—N3	1.330 (5)	C10—C11	1.393 (5)
C2—N2	1.358 (5)	C11—C12	1.386 (5)
C2—S1	1.688 (4)	C11—H11	0.9500
N2—H2	0.73 (4)	C12—C13	1.376 (6)
N3—C9	1.461 (5)	C12—H12	0.9500
N3—H3	0.76 (4)	C13—C14	1.387 (6)
C3—C8	1.396 (5)	C13—H13	0.9500
C3—C4	1.398 (5)	C14—C15	1.384 (5)
C4—C5	1.384 (5)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.379 (5)	C16—C17	1.532 (5)
C5—H5	0.9500	C16—H16A	0.9900
C6—C7	1.386 (5)	C16—H16B	0.9900
C6—Br1	1.897 (4)	C17—H17A	0.9800
C7—C8	1.376 (5)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800

O1—C1—N1	121.7 (3)	C16—C9—C10	115.4 (3)
O1—C1—C3	121.8 (3)	N3—C9—H9	106.8
N1—C1—C3	116.5 (3)	C16—C9—H9	106.8
C1—N1—N2	119.3 (3)	C10—C9—H9	106.8
C1—N1—H1	115 (3)	C15—C10—C11	118.6 (3)
N2—N1—H1	119 (3)	C15—C10—C9	123.3 (3)
N3—C2—N2	117.1 (3)	C11—C10—C9	118.2 (3)
N3—C2—S1	124.3 (3)	C12—C11—C10	120.7 (4)
N2—C2—S1	118.6 (3)	C12—C11—H11	119.6
C2—N2—N1	120.4 (3)	C10—C11—H11	119.6
C2—N2—H2	118 (3)	C13—C12—C11	120.0 (4)
N1—N2—H2	113 (3)	C13—C12—H12	120.0
C2—N3—C9	125.5 (3)	C11—C12—H12	120.0
C2—N3—H3	117 (3)	C12—C13—C14	120.0 (4)
C9—N3—H3	117 (3)	C12—C13—H13	120.0
C8—C3—C4	118.8 (3)	C14—C13—H13	120.0
C8—C3—C1	117.0 (3)	C15—C14—C13	119.7 (4)
C4—C3—C1	124.2 (3)	C15—C14—H14	120.2
C5—C4—C3	120.4 (3)	C13—C14—H14	120.2
C5—C4—H4	119.8	C10—C15—C14	121.1 (4)
C3—C4—H4	119.8	C10—C15—H15	119.5
C6—C5—C4	119.2 (3)	C14—C15—H15	119.5
C6—C5—H5	120.4	C9—C16—C17	111.8 (3)
C4—C5—H5	120.4	C9—C16—H16A	109.3
C5—C6—C7	121.5 (4)	C17—C16—H16A	109.3
C5—C6—Br1	119.0 (3)	C9—C16—H16B	109.3
C7—C6—Br1	119.5 (3)	C17—C16—H16B	109.3
C8—C7—C6	118.9 (3)	H16A—C16—H16B	107.9
C8—C7—H7	120.5	C16—C17—H17A	109.5
C6—C7—H7	120.5	C16—C17—H17B	109.5
C7—C8—C3	121.0 (3)	H17A—C17—H17B	109.5
C7—C8—H8	119.5	C16—C17—H17C	109.5
C3—C8—H8	119.5	H17A—C17—H17C	109.5
N3—C9—C16	109.8 (3)	H17B—C17—H17C	109.5
N3—C9—C10	110.8 (3)

O1—C1—N1—N2	−13.7 (5)	C4—C3—C8—C7	−1.1 (6)
C3—C1—N1—N2	166.7 (3)	C1—C3—C8—C7	176.6 (3)
N3—C2—N2—N1	−26.7 (4)	C2—N3—C9—C16	−125.2 (3)
S1—C2—N2—N1	154.7 (2)	C2—N3—C9—C10	106.1 (4)
C1—N1—N2—C2	131.2 (3)	N3—C9—C10—C15	121.4 (4)
N2—C2—N3—C9	175.6 (3)	C16—C9—C10—C15	−4.2 (5)
S1—C2—N3—C9	−6.0 (4)	N3—C9—C10—C11	−58.7 (4)
O1—C1—C3—C8	−5.4 (5)	C16—C9—C10—C11	175.7 (3)
N1—C1—C3—C8	174.2 (3)	C15—C10—C11—C12	−0.8 (6)
O1—C1—C3—C4	172.1 (3)	C9—C10—C11—C12	179.3 (3)
N1—C1—C3—C4	−8.3 (5)	C10—C11—C12—C13	0.8 (6)
C8—C3—C4—C5	0.8 (5)	C11—C12—C13—C14	−0.1 (6)
C1—C3—C4—C5	−176.7 (3)	C12—C13—C14—C15	−0.5 (6)
C3—C4—C5—C6	0.2 (5)	C11—C10—C15—C14	0.2 (6)
C4—C5—C6—C7	−1.1 (6)	C9—C10—C15—C14	−180.0 (4)
C4—C5—C6—Br1	178.7 (3)	C13—C14—C15—C10	0.5 (6)
C5—C6—C7—C8	0.8 (6)	N3—C9—C16—C17	57.4 (4)
Br1—C6—C7—C8	−179.0 (3)	C10—C9—C16—C17	−176.5 (3)
C6—C7—C8—C3	0.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.84 (4)	2.03 (4)	2.834 (4)	161 (4)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈BrN₃OS
M_r	392.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	123
a, b, c (Å)	6.263 (3), 9.698 (5), 27.651 (15)
V (Å³)	1679.5 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.58
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Integration (NUMABS; Higashi, 1999)
T_min, T_max	0.512, 0.627
No. of measured, independent and observed [I > 2σ(I)] reflections	13732, 3824, 3516
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.074, 1.13
No. of reflections	3824
No. of parameters	219
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35
Absolute structure	Flack (1983), 1584 Friedel pairs
Absolute structure parameter	0.020 (10)

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), TEXSAN (Molecular Structure Corporation & Rigaku, 2004), SIR97 (Altomare et al., 1999), ORTEPII (Johnson, 1976), SHELXL97 (Sheldrick, 2008) and TEXSAN (Molecular Structure Corporation & Rigaku, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.84 (4)	2.03 (4)	2.834 (4)	161 (4)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative program for Doctoral Fellowships at Gifu University, Japan.

References

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