3-[2-Hy­droxy-3-(2,4,6-trimethyl­phen­yl)prop­yl]-3-methyl-1-phenyl­thio­urea

Maharramov, A.M.; Khalilov, A.N.; Sadikhova, N.D.; Gurbanov, A.V.; Ng, S.W.

doi:10.1107/S1600536811012736

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1087

doi:10.1107/S1600536811012736

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3-[2-Hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea

Abel M. Maharramov,^a Ali N. Khalilov,^a Nurlana D. Sadikhova,^a Atash V. Gurbanov ^a and Seik Weng Ng ^b ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 March 2011; accepted 6 April 2011; online 13 April 2011)

In the title compound, C₂₀H₂₆N₂OS, four non-H atoms of the thiourea unit are approximately planar (r.m.s. deviation = 0.005 Å); the phenyl and benzene rings are twisted out of this plane by 28.55 (7) and 60.00 (7)°, respectively. An intramolecular N—H⋯O hydrogen bond occurs. The hydroxy group is hydrogen bonded to the double-bond S atom of an inversion-related molecule, generating a hydrogen-bonded dimer in the crystal structure.

Related literature

The title compund was prepared by a reaction of 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol and phenyl isothiocyanate; for the structure of the reactant 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol, see: Maharramov et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₆N₂OS
M_r = 342.49
Monoclinic, P 2₁ /c
a = 14.6313 (11) Å
b = 8.1579 (6) Å
c = 16.4455 (12) Å
β = 109.040 (1)°
V = 1855.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.964
10052 measured reflections
4160 independent reflections
3542 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.04
4160 reflections
229 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1ⁱ	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2⋯O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012736/xu5185sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012736/xu5185Isup2.hkl

checkCIF report

Comment top

We have recently reported the synthesis and crystal structure of 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol (Maharramov et al., 2011). This secondary amine behaves like a conventional secondary amine in its reaction with phenyl isothiocyanate to furnish a thiourea (Scheme I). The four-atoms N–C(═S)–N unit of C₂₀H₂₆N₂OS is planar [r.m.s. deviation 0.005 Å]; the phenyl ring connected to one of the two flanking N atoms is twisted out of this plane 28.6 (1)° (Fig. 1). The propyl chain connected to the other N atom bears a hydroxy substituent; this serves as hydrogen-bond donor acceptor to the double-bond S atom of an inversion-related molecule to generate a hydrogen-bonded dimer.

Related literature top

Experimental top

1-Methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol was synthesized as reported (Maharramov et al., 2011). The compound (10 mmol) and phenyl isothiocyanate (10 mmol) were heated in benzene (50 mol) for 10 h. The solvent was removed and the product recrystallized from ethanol to yield colorless crystals, m.p. 413–414 K; yield 90%.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₂₆N₂OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-[2-Hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea top

Crystal data top

C₂₀H₂₆N₂OS	F(000) = 736
M_r = 342.49	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4968 reflections
a = 14.6313 (11) Å	θ = 2.6–29.2°
b = 8.1579 (6) Å	µ = 0.18 mm⁻¹
c = 16.4455 (12) Å	T = 100 K
β = 109.040 (1)°	Prism, colorless
V = 1855.6 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4160 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.947, T_max = 0.964	k = −10→10
10052 measured reflections	l = −20→20

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0617P)² + 0.4837P] where P = (F_o² + 2F_c²)/3
4160 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.38 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₂₆N₂OS	V = 1855.6 (2) Å³
M_r = 342.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6313 (11) Å	µ = 0.18 mm⁻¹
b = 8.1579 (6) Å	T = 100 K
c = 16.4455 (12) Å	0.30 × 0.20 × 0.20 mm
β = 109.040 (1)°

Data collection top

Bruker SMART APEX diffractometer	4160 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3542 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.964	R_int = 0.028
10052 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.38 e Å⁻³
4160 reflections	Δρ_min = −0.24 e Å⁻³
229 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.35275 (3)	0.49063 (4)	0.61941 (2)	0.02172 (11)
O1	0.61082 (7)	0.26588 (12)	0.52099 (7)	0.0223 (2)
H1	0.6434 (13)	0.330 (2)	0.5027 (12)	0.041 (6)*
N1	0.51088 (8)	0.30365 (14)	0.65553 (7)	0.0197 (3)
N2	0.42327 (8)	0.31882 (14)	0.51317 (8)	0.0196 (2)
H2	0.4785 (9)	0.292 (2)	0.5069 (12)	0.032 (5)*
C1	0.81508 (10)	0.13935 (16)	0.59751 (10)	0.0216 (3)
C2	0.89199 (11)	0.21843 (18)	0.65953 (10)	0.0260 (3)
C3	0.97052 (11)	0.2735 (2)	0.63719 (12)	0.0320 (4)
H3	1.0215	0.3293	0.6790	0.038*
C4	0.97654 (12)	0.2495 (2)	0.55560 (12)	0.0340 (4)
C5	0.90094 (12)	0.1692 (2)	0.49568 (11)	0.0319 (4)
H5	0.9043	0.1508	0.4397	0.038*
C6	0.82014 (11)	0.11434 (18)	0.51461 (10)	0.0254 (3)
C7	0.89290 (13)	0.2418 (2)	0.75097 (11)	0.0364 (4)
H7A	0.9484	0.3098	0.7824	0.055*
H7B	0.8979	0.1348	0.7792	0.055*
H7C	0.8330	0.2961	0.7506	0.055*
C8	1.06343 (14)	0.3063 (2)	0.53256 (16)	0.0496 (5)
H8A	1.0423	0.3813	0.4834	0.074*
H8B	1.0956	0.2112	0.5174	0.074*
H8C	1.1087	0.3630	0.5819	0.074*
C9	0.74118 (12)	0.0268 (2)	0.44548 (11)	0.0327 (4)
H9A	0.7578	0.0233	0.3924	0.049*
H9B	0.6800	0.0856	0.4348	0.049*
H9C	0.7345	−0.0852	0.4643	0.049*
C10	0.72773 (10)	0.08517 (17)	0.62059 (10)	0.0223 (3)
H10A	0.7491	0.0465	0.6810	0.027*
H10B	0.6964	−0.0080	0.5834	0.027*
C11	0.65378 (10)	0.22347 (17)	0.61007 (9)	0.0195 (3)
H11	0.6861	0.3218	0.6435	0.023*
C12	0.57030 (10)	0.16888 (16)	0.64028 (9)	0.0195 (3)
H12A	0.5280	0.0943	0.5965	0.023*
H12B	0.5971	0.1057	0.6942	0.023*
C13	0.54069 (11)	0.36552 (19)	0.74324 (9)	0.0253 (3)
H13A	0.5239	0.4819	0.7427	0.038*
H13B	0.6107	0.3523	0.7697	0.038*
H13C	0.5075	0.3040	0.7765	0.038*
C14	0.43142 (10)	0.36483 (16)	0.59459 (9)	0.0175 (3)
C15	0.34745 (10)	0.33743 (15)	0.43473 (9)	0.0177 (3)
C16	0.25039 (10)	0.36157 (17)	0.42568 (10)	0.0228 (3)
H16	0.2307	0.3745	0.4749	0.027*
C17	0.18274 (11)	0.36650 (18)	0.34365 (10)	0.0274 (3)
H17	0.1166	0.3841	0.3374	0.033*
C18	0.20929 (11)	0.34643 (19)	0.27106 (10)	0.0280 (3)
H18	0.1619	0.3497	0.2155	0.034*
C19	0.30580 (11)	0.32148 (18)	0.28011 (9)	0.0251 (3)
H19	0.3249	0.3065	0.2307	0.030*
C20	0.37432 (10)	0.31839 (16)	0.36127 (9)	0.0212 (3)
H20	0.4405	0.3031	0.3671	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0242 (2)	0.02255 (18)	0.0209 (2)	0.00347 (13)	0.01083 (14)	0.00010 (13)
O1	0.0211 (5)	0.0255 (5)	0.0227 (5)	0.0022 (4)	0.0102 (4)	0.0086 (4)
N1	0.0209 (6)	0.0219 (6)	0.0169 (6)	0.0021 (4)	0.0072 (5)	0.0012 (4)
N2	0.0176 (6)	0.0247 (6)	0.0176 (6)	0.0025 (5)	0.0074 (5)	0.0004 (5)
C1	0.0210 (7)	0.0185 (6)	0.0264 (7)	0.0061 (5)	0.0092 (6)	0.0057 (5)
C2	0.0215 (7)	0.0253 (7)	0.0294 (8)	0.0078 (6)	0.0056 (6)	0.0039 (6)
C3	0.0195 (7)	0.0279 (8)	0.0450 (10)	0.0049 (6)	0.0057 (7)	0.0036 (7)
C4	0.0255 (8)	0.0285 (8)	0.0531 (11)	0.0098 (6)	0.0196 (7)	0.0149 (7)
C5	0.0342 (9)	0.0333 (8)	0.0348 (9)	0.0116 (7)	0.0203 (7)	0.0108 (7)
C6	0.0267 (8)	0.0221 (7)	0.0285 (8)	0.0090 (6)	0.0105 (6)	0.0062 (6)
C7	0.0317 (9)	0.0433 (10)	0.0289 (9)	0.0076 (7)	0.0029 (7)	−0.0013 (7)
C8	0.0328 (10)	0.0438 (11)	0.0815 (16)	0.0091 (8)	0.0315 (10)	0.0224 (10)
C9	0.0361 (9)	0.0370 (9)	0.0247 (8)	0.0071 (7)	0.0096 (7)	−0.0018 (7)
C10	0.0236 (7)	0.0190 (6)	0.0257 (7)	0.0040 (5)	0.0101 (6)	0.0064 (5)
C11	0.0198 (7)	0.0193 (6)	0.0201 (7)	0.0017 (5)	0.0074 (5)	0.0045 (5)
C12	0.0197 (7)	0.0186 (6)	0.0211 (7)	0.0013 (5)	0.0080 (5)	0.0039 (5)
C13	0.0280 (8)	0.0306 (8)	0.0167 (7)	−0.0006 (6)	0.0064 (6)	−0.0002 (6)
C14	0.0192 (7)	0.0162 (6)	0.0188 (7)	−0.0029 (5)	0.0086 (5)	0.0009 (5)
C15	0.0200 (7)	0.0148 (6)	0.0183 (7)	−0.0014 (5)	0.0061 (5)	−0.0005 (5)
C16	0.0215 (7)	0.0233 (7)	0.0246 (7)	−0.0015 (5)	0.0089 (6)	−0.0005 (6)
C17	0.0185 (7)	0.0290 (8)	0.0315 (8)	−0.0016 (6)	0.0039 (6)	0.0005 (6)
C18	0.0272 (8)	0.0293 (8)	0.0218 (8)	−0.0048 (6)	0.0000 (6)	0.0012 (6)
C19	0.0311 (8)	0.0259 (7)	0.0177 (7)	−0.0043 (6)	0.0070 (6)	−0.0006 (6)
C20	0.0220 (7)	0.0207 (6)	0.0220 (7)	−0.0019 (5)	0.0086 (6)	−0.0011 (5)

Geometric parameters (Å, º) top

S1—C14	1.6885 (14)	C8—H8C	0.9800
O1—C11	1.4353 (17)	C9—H9A	0.9800
O1—H1	0.826 (9)	C9—H9B	0.9800
N1—C14	1.3583 (17)	C9—H9C	0.9800
N1—C13	1.4544 (18)	C10—C11	1.5333 (19)
N1—C12	1.4730 (17)	C10—H10A	0.9900
N2—C14	1.3578 (18)	C10—H10B	0.9900
N2—C15	1.4086 (17)	C11—C12	1.5275 (19)
N2—H2	0.875 (9)	C11—H11	1.0000
C1—C6	1.404 (2)	C12—H12A	0.9900
C1—C2	1.405 (2)	C12—H12B	0.9900
C1—C10	1.5130 (19)	C13—H13A	0.9800
C2—C3	1.390 (2)	C13—H13B	0.9800
C2—C7	1.512 (2)	C13—H13C	0.9800
C3—C4	1.387 (3)	C15—C16	1.393 (2)
C3—H3	0.9500	C15—C20	1.396 (2)
C4—C5	1.383 (3)	C16—C17	1.389 (2)
C4—C8	1.513 (2)	C16—H16	0.9500
C5—C6	1.391 (2)	C17—C18	1.380 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C9	1.510 (2)	C18—C19	1.386 (2)
C7—H7A	0.9800	C18—H18	0.9500
C7—H7B	0.9800	C19—C20	1.3835 (19)
C7—H7C	0.9800	C19—H19	0.9500
C8—H8A	0.9800	C20—H20	0.9500
C8—H8B	0.9800

C11—O1—H1	114.3 (14)	C1—C10—H10A	109.1
C14—N1—C13	120.79 (12)	C11—C10—H10A	109.1
C14—N1—C12	124.00 (12)	C1—C10—H10B	109.1
C13—N1—C12	115.16 (11)	C11—C10—H10B	109.1
C14—N2—C15	131.51 (12)	H10A—C10—H10B	107.9
C14—N2—H2	113.4 (12)	O1—C11—C12	105.77 (11)
C15—N2—H2	113.7 (12)	O1—C11—C10	110.52 (11)
C6—C1—C2	119.22 (14)	C12—C11—C10	111.01 (11)
C6—C1—C10	121.17 (13)	O1—C11—H11	109.8
C2—C1—C10	119.61 (13)	C12—C11—H11	109.8
C3—C2—C1	119.47 (15)	C10—C11—H11	109.8
C3—C2—C7	118.83 (15)	N1—C12—C11	114.64 (11)
C1—C2—C7	121.68 (14)	N1—C12—H12A	108.6
C4—C3—C2	121.91 (16)	C11—C12—H12A	108.6
C4—C3—H3	119.0	N1—C12—H12B	108.6
C2—C3—H3	119.0	C11—C12—H12B	108.6
C5—C4—C3	117.90 (15)	H12A—C12—H12B	107.6
C5—C4—C8	120.58 (17)	N1—C13—H13A	109.5
C3—C4—C8	121.51 (18)	N1—C13—H13B	109.5
C4—C5—C6	122.24 (16)	H13A—C13—H13B	109.5
C4—C5—H5	118.9	N1—C13—H13C	109.5
C6—C5—H5	118.9	H13A—C13—H13C	109.5
C5—C6—C1	119.24 (15)	H13B—C13—H13C	109.5
C5—C6—C9	118.75 (15)	N2—C14—N1	113.87 (12)
C1—C6—C9	122.01 (14)	N2—C14—S1	123.98 (10)
C2—C7—H7A	109.5	N1—C14—S1	122.12 (10)
C2—C7—H7B	109.5	C16—C15—C20	119.25 (13)
H7A—C7—H7B	109.5	C16—C15—N2	125.74 (13)
C2—C7—H7C	109.5	C20—C15—N2	114.87 (12)
H7A—C7—H7C	109.5	C17—C16—C15	119.10 (14)
H7B—C7—H7C	109.5	C17—C16—H16	120.4
C4—C8—H8A	109.5	C15—C16—H16	120.4
C4—C8—H8B	109.5	C18—C17—C16	121.61 (14)
H8A—C8—H8B	109.5	C18—C17—H17	119.2
C4—C8—H8C	109.5	C16—C17—H17	119.2
H8A—C8—H8C	109.5	C17—C18—C19	119.26 (14)
H8B—C8—H8C	109.5	C17—C18—H18	120.4
C6—C9—H9A	109.5	C19—C18—H18	120.4
C6—C9—H9B	109.5	C20—C19—C18	119.91 (14)
H9A—C9—H9B	109.5	C20—C19—H19	120.0
C6—C9—H9C	109.5	C18—C19—H19	120.0
H9A—C9—H9C	109.5	C19—C20—C15	120.85 (13)
H9B—C9—H9C	109.5	C19—C20—H20	119.6
C1—C10—C11	112.30 (11)	C15—C20—H20	119.6

C6—C1—C2—C3	1.4 (2)	C14—N1—C12—C11	90.19 (16)
C10—C1—C2—C3	−177.61 (13)	C13—N1—C12—C11	−92.18 (14)
C6—C1—C2—C7	−177.09 (13)	O1—C11—C12—N1	−76.40 (14)
C10—C1—C2—C7	3.9 (2)	C10—C11—C12—N1	163.70 (12)
C1—C2—C3—C4	−1.5 (2)	C15—N2—C14—N1	170.80 (13)
C7—C2—C3—C4	177.01 (14)	C15—N2—C14—S1	−10.8 (2)
C2—C3—C4—C5	0.5 (2)	C13—N1—C14—N2	167.94 (12)
C2—C3—C4—C8	−178.50 (15)	C12—N1—C14—N2	−14.56 (18)
C3—C4—C5—C6	0.6 (2)	C13—N1—C14—S1	−10.48 (18)
C8—C4—C5—C6	179.65 (15)	C12—N1—C14—S1	167.02 (10)
C4—C5—C6—C1	−0.7 (2)	C14—N2—C15—C16	−22.3 (2)
C4—C5—C6—C9	−179.63 (14)	C14—N2—C15—C20	162.14 (13)
C2—C1—C6—C5	−0.3 (2)	C20—C15—C16—C17	−0.2 (2)
C10—C1—C6—C5	178.68 (13)	N2—C15—C16—C17	−175.56 (13)
C2—C1—C6—C9	178.57 (13)	C15—C16—C17—C18	0.7 (2)
C10—C1—C6—C9	−2.4 (2)	C16—C17—C18—C19	−0.3 (2)
C6—C1—C10—C11	−94.33 (16)	C17—C18—C19—C20	−0.6 (2)
C2—C1—C10—C11	84.66 (16)	C18—C19—C20—C15	1.1 (2)
C1—C10—C11—O1	67.26 (15)	C16—C15—C20—C19	−0.7 (2)
C1—C10—C11—C12	−175.70 (12)	N2—C15—C20—C19	175.19 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2···O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₂OS
M_r	342.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.6313 (11), 8.1579 (6), 16.4455 (12)
β (°)	109.040 (1)
V (Å³)	1855.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	10052, 4160, 3542
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.04
No. of reflections	4160
No. of parameters	229
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ⁱ	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2···O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank Baku State University and the University of Malaya for supporting this study.

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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