1,2-Bis[N′-(2,2-dimethyl­propionyl)thio­ureido]cyclo­hexa­ne

Yusof, M.S.M.; Ayob, N.A.C.; Kadir, M.A.; Yamin, B.M.

doi:10.1107/S1600536808011495

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o937

doi:10.1107/S1600536808011495

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1,2-Bis[N′-(2,2-dimethylpropionyl)thioureido]cyclohexane

M. Sukeri M. Yusof,^a ^* Noor Adila C. Ayob,^a Maisara A. Kadir ^b and Bohari M. Yamin ^b

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
^*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 20 April 2008; accepted 22 April 2008; online 30 April 2008)

In the title compound, C₁₈H₃₂N₄O₂S₂, the dihedral angle between the two thiourea groups is 78.55 (7)°. The molecular conformation is stabilized by intramolecular N—H⋯O hydrogen bonds and the crystal structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related crystal structures, see: Thiam et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₃₂N₄O₂S₂
M_r = 400.60
Monoclinic, P 2₁ /c
a = 10.960 (2) Å
b = 19.065 (4) Å
c = 10.378 (2) Å
β = 96.112 (4)°
V = 2156.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 298 (2) K
0.48 × 0.41 × 0.37 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.883, T_max = 0.908
10928 measured reflections
3779 independent reflections
2828 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.124
S = 1.07
3779 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	1.97	2.650 (2)	135
N3—H3⋯O2	0.86	1.99	2.670 (2)	135
N1—H1⋯O2ⁱ	0.86	2.25	3.078 (2)	161
C1—H1B⋯O2ⁱ	0.96	2.54	3.462 (3)	161
Symmetry code: (i) -x, -y, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011495/bt2701sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011495/bt2701Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is a propionylthiourea derivatives and analogous to 1,2-bis(N'-benzoylthioureido)benzene, (Thiam et al., 2008), except that the benzene and benzoyl groups are replaced by cyclohexane and 2,2-dimethylpropionyl group respectively (Fig. 1). The bond lengths and angles are in normal ranges (Allen et al., 1987). The thiourea fragments [S1/N1/N2/C4 and S2/N3/N4/C11] are all planar, with a maximum deviation of 0.024 (2)Å from least-sqares plane for atom N2 and the dihedral angles between them is 78.55 (7)°.

There are two intramolecular hydrogen bonds, N2—H2···O1 and N3—H3···O2 (Table 1), forming two pseudo-six-membered rings (O1···H2—N2—C4—N1—C3—O1 and O2···H3—N3—C11—N4—C12—O2). In the crystal structure, the molecules are linked by intermolecular interactions, N—H···O and C—H···O forming centrosymmetric dimers (Fig. 2).

Related literature top

For related crystal structures, see: Thiam et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

To a stirring acetone solution (75 ml) of pivaloyl chloride (5.0 g, 0.04 mol) and ammonium thiocyanate (3.15 g, 0.04 mol), 1,2-diaminocyclohexane (2.37 g, 0.02 mol) in 40 ml of acetone was added dropwise. The solution mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol before dried under vacuum. Good quality crystals were obtained by recrystallization from DMSO.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. : The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. : Packing diagram of the title compound viewed down the b axis. The dashed lines denote hydrogen bonds.

1,2-Bis[N'-(2,2-dimethylpropionyl)thioureido]cyclohexane top

Crystal data top

C₁₈H₃₂N₄O₂S₂	F(000) = 864
M_r = 400.60	D_x = 1.234 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 982 reflections
a = 10.960 (2) Å	θ = 1.9–25.0°
b = 19.065 (4) Å	µ = 0.27 mm⁻¹
c = 10.378 (2) Å	T = 298 K
β = 96.112 (4)°	Block, colourless
V = 2156.1 (8) Å³	0.48 × 0.41 × 0.37 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3779 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ω scans	h = −9→13
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −22→22
T_min = 0.883, T_max = 0.908	l = −12→11
10928 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0662P)² + 0.3145P] where P = (F_o² + 2F_c²)/3
3779 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₃₂N₄O₂S₂	V = 2156.1 (8) Å³
M_r = 400.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.960 (2) Å	µ = 0.27 mm⁻¹
b = 19.065 (4) Å	T = 298 K
c = 10.378 (2) Å	0.48 × 0.41 × 0.37 mm
β = 96.112 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3779 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2828 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.908	R_int = 0.026
10928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.07	Δρ_max = 0.30 e Å⁻³
3779 reflections	Δρ_min = −0.22 e Å⁻³
241 parameters

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
S1	0.12804 (6)	0.05301 (3)	−0.07986 (6)	0.0544 (2)
S2	0.03271 (6)	0.10826 (4)	0.56450 (6)	0.0689 (2)
O1	0.26724 (16)	−0.05371 (8)	0.29928 (15)	0.0566 (4)
O2	−0.21983 (13)	0.10785 (8)	0.19001 (14)	0.0464 (4)
N1	0.20717 (16)	−0.04742 (8)	0.08323 (17)	0.0424 (4)
H1	0.1996	−0.0721	0.0135	0.051*
N2	0.18658 (16)	0.06134 (8)	0.17475 (17)	0.0426 (4)
H2	0.2023	0.0397	0.2473	0.051*
N3	0.00442 (15)	0.13012 (9)	0.31031 (18)	0.0435 (4)
H3	−0.0426	0.1273	0.2387	0.052*
N4	−0.15887 (16)	0.08040 (10)	0.39865 (18)	0.0481 (5)
H4	−0.1840	0.0617	0.4664	0.058*
C1	0.1676 (3)	−0.19515 (13)	0.0914 (3)	0.0723 (8)
H1A	0.1771	−0.2452	0.0940	0.108*
H1B	0.1685	−0.1790	0.0039	0.108*
H1C	0.0910	−0.1827	0.1222	0.108*
C2	0.2729 (2)	−0.16111 (11)	0.1774 (2)	0.0468 (5)
C3	0.24848 (19)	−0.08288 (11)	0.1939 (2)	0.0415 (5)
C4	0.17546 (18)	0.02355 (11)	0.0674 (2)	0.0396 (5)
C5	0.17396 (18)	0.13730 (10)	0.1781 (2)	0.0391 (5)
H5	0.1138	0.1516	0.1063	0.047*
C6	0.2965 (2)	0.17181 (11)	0.1603 (2)	0.0462 (5)
H6A	0.3591	0.1529	0.2239	0.055*
H6B	0.3190	0.1603	0.0749	0.055*
C7	0.2932 (2)	0.25092 (11)	0.1746 (2)	0.0523 (6)
H7A	0.3743	0.2701	0.1682	0.063*
H7B	0.2375	0.2708	0.1053	0.063*
C8	0.2512 (2)	0.27047 (12)	0.3043 (2)	0.0564 (6)
H8A	0.3100	0.2534	0.3736	0.068*
H8B	0.2469	0.3211	0.3115	0.068*
C9	0.1265 (2)	0.23904 (11)	0.3176 (2)	0.0480 (6)
H9A	0.0671	0.2586	0.2513	0.058*
H9B	0.1014	0.2516	0.4014	0.058*
C10	0.12704 (18)	0.15951 (10)	0.3048 (2)	0.0396 (5)
H10	0.1819	0.1401	0.3767	0.048*
C11	−0.03989 (18)	0.10766 (11)	0.4159 (2)	0.0421 (5)
C12	−0.24141 (18)	0.07907 (11)	0.2897 (2)	0.0387 (5)
C13	−0.36266 (19)	0.04254 (11)	0.3039 (2)	0.0436 (5)
C14	−0.3419 (2)	−0.03052 (14)	0.3627 (3)	0.0676 (8)
H14A	−0.4196	−0.0533	0.3662	0.101*
H14B	−0.3006	−0.0265	0.4487	0.101*
H14C	−0.2926	−0.0577	0.3101	0.101*
C15	0.3909 (2)	−0.16947 (14)	0.1128 (3)	0.0769 (9)
H15A	0.4573	−0.1469	0.1647	0.115*
H15B	0.3805	−0.1484	0.0283	0.115*
H15C	0.4091	−0.2184	0.1047	0.115*
C16	0.2847 (4)	−0.19545 (14)	0.3097 (3)	0.1025 (13)
H16A	0.3535	−0.1757	0.3624	0.154*
H16B	0.2971	−0.2450	0.3004	0.154*
H16C	0.2112	−0.1875	0.3502	0.154*
C17	−0.4349 (2)	0.03560 (15)	0.1708 (2)	0.0607 (7)
H17A	−0.4482	0.0813	0.1330	0.091*
H17B	−0.5126	0.0138	0.1795	0.091*
H17C	−0.3895	0.0073	0.1161	0.091*
C18	−0.4344 (2)	0.08752 (15)	0.3912 (3)	0.0649 (7)
H18A	−0.4380	0.1349	0.3598	0.097*
H18B	−0.3941	0.0866	0.4780	0.097*
H18C	−0.5161	0.0693	0.3907	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0754 (4)	0.0458 (4)	0.0412 (3)	0.0087 (3)	0.0030 (3)	0.0069 (3)
S2	0.0585 (4)	0.0989 (6)	0.0462 (4)	−0.0190 (4)	−0.0089 (3)	0.0110 (3)
O1	0.0847 (12)	0.0408 (9)	0.0420 (10)	0.0074 (8)	−0.0043 (8)	−0.0010 (7)
O2	0.0466 (9)	0.0556 (9)	0.0366 (9)	−0.0066 (7)	0.0027 (6)	0.0042 (7)
N1	0.0578 (11)	0.0324 (9)	0.0363 (10)	0.0027 (8)	0.0014 (8)	−0.0020 (8)
N2	0.0563 (11)	0.0337 (9)	0.0376 (10)	0.0042 (8)	0.0039 (8)	0.0023 (8)
N3	0.0363 (9)	0.0525 (11)	0.0411 (11)	−0.0040 (8)	0.0011 (8)	−0.0005 (8)
N4	0.0415 (10)	0.0599 (12)	0.0423 (11)	−0.0091 (9)	0.0012 (8)	0.0127 (9)
C1	0.0789 (19)	0.0417 (14)	0.096 (2)	−0.0145 (13)	0.0081 (16)	−0.0041 (14)
C2	0.0633 (15)	0.0318 (11)	0.0454 (13)	0.0014 (10)	0.0067 (11)	0.0026 (10)
C3	0.0472 (12)	0.0355 (11)	0.0416 (13)	−0.0012 (9)	0.0045 (10)	0.0017 (10)
C4	0.0414 (12)	0.0351 (11)	0.0431 (13)	0.0009 (9)	0.0080 (9)	0.0011 (9)
C5	0.0413 (11)	0.0320 (11)	0.0437 (12)	0.0075 (9)	0.0031 (9)	0.0018 (9)
C6	0.0430 (12)	0.0453 (12)	0.0514 (14)	0.0050 (10)	0.0094 (10)	−0.0004 (10)
C7	0.0501 (13)	0.0433 (13)	0.0645 (16)	−0.0060 (10)	0.0108 (11)	0.0003 (11)
C8	0.0619 (15)	0.0435 (13)	0.0646 (16)	−0.0077 (11)	0.0103 (12)	−0.0097 (12)
C9	0.0486 (13)	0.0422 (12)	0.0543 (14)	0.0061 (10)	0.0105 (11)	−0.0072 (11)
C10	0.0326 (11)	0.0402 (12)	0.0456 (13)	0.0005 (9)	0.0019 (9)	−0.0014 (10)
C11	0.0402 (12)	0.0401 (12)	0.0456 (13)	−0.0009 (9)	0.0025 (10)	0.0032 (10)
C12	0.0417 (12)	0.0366 (11)	0.0377 (12)	0.0042 (9)	0.0044 (9)	−0.0012 (9)
C13	0.0362 (11)	0.0522 (13)	0.0426 (13)	−0.0029 (10)	0.0058 (9)	0.0025 (10)
C14	0.0560 (15)	0.0608 (16)	0.086 (2)	−0.0131 (13)	0.0092 (14)	0.0163 (15)
C15	0.0644 (17)	0.0511 (15)	0.117 (3)	0.0140 (13)	0.0166 (17)	0.0041 (16)
C16	0.214 (4)	0.0405 (15)	0.0529 (18)	0.0181 (19)	0.011 (2)	0.0113 (13)
C17	0.0458 (13)	0.0868 (18)	0.0492 (15)	−0.0151 (13)	0.0037 (11)	−0.0059 (13)
C18	0.0494 (14)	0.088 (2)	0.0584 (17)	0.0067 (13)	0.0092 (12)	−0.0083 (14)

Geometric parameters (Å, º) top

S1—C4	1.659 (2)	C7—C8	1.515 (3)
S2—C11	1.658 (2)	C7—H7A	0.9700
O1—C3	1.224 (2)	C7—H7B	0.9700
O2—C12	1.217 (2)	C8—C9	1.512 (3)
N1—C3	1.368 (3)	C8—H8A	0.9700
N1—C4	1.402 (3)	C8—H8B	0.9700
N1—H1	0.8600	C9—C10	1.522 (3)
N2—C4	1.322 (3)	C9—H9A	0.9700
N2—C5	1.455 (2)	C9—H9B	0.9700
N2—H2	0.8600	C10—H10	0.9800
N3—C11	1.317 (3)	C12—C13	1.521 (3)
N3—C10	1.463 (3)	C13—C17	1.522 (3)
N3—H3	0.8600	C13—C18	1.525 (3)
N4—C12	1.371 (3)	C13—C14	1.528 (3)
N4—C11	1.397 (3)	C14—H14A	0.9600
N4—H4	0.8600	C14—H14B	0.9600
C1—C2	1.526 (4)	C14—H14C	0.9600
C1—H1A	0.9600	C15—H15A	0.9600
C1—H1B	0.9600	C15—H15B	0.9600
C1—H1C	0.9600	C15—H15C	0.9600
C2—C16	1.514 (3)	C16—H16A	0.9600
C2—C15	1.528 (4)	C16—H16B	0.9600
C2—C3	1.528 (3)	C16—H16C	0.9600
C5—C10	1.522 (3)	C17—H17A	0.9600
C5—C6	1.524 (3)	C17—H17B	0.9600
C5—H5	0.9800	C17—H17C	0.9600
C6—C7	1.516 (3)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600

C3—N1—C4	129.13 (18)	C8—C9—C10	112.04 (18)
C3—N1—H1	115.4	C8—C9—H9A	109.2
C4—N1—H1	115.4	C10—C9—H9A	109.2
C4—N2—C5	124.21 (18)	C8—C9—H9B	109.2
C4—N2—H2	117.9	C10—C9—H9B	109.2
C5—N2—H2	117.9	H9A—C9—H9B	107.9
C11—N3—C10	125.39 (18)	N3—C10—C5	108.89 (16)
C11—N3—H3	117.3	N3—C10—C9	111.49 (16)
C10—N3—H3	117.3	C5—C10—C9	110.94 (17)
C12—N4—C11	129.61 (18)	N3—C10—H10	108.5
C12—N4—H4	115.2	C5—C10—H10	108.5
C11—N4—H4	115.2	C9—C10—H10	108.5
C2—C1—H1A	109.5	N3—C11—N4	115.86 (18)
C2—C1—H1B	109.5	N3—C11—S2	126.07 (16)
H1A—C1—H1B	109.5	N4—C11—S2	118.07 (16)
C2—C1—H1C	109.5	O2—C12—N4	121.47 (19)
H1A—C1—H1C	109.5	O2—C12—C13	122.65 (18)
H1B—C1—H1C	109.5	N4—C12—C13	115.82 (18)
C16—C2—C1	109.5 (2)	C12—C13—C17	109.11 (18)
C16—C2—C15	111.0 (2)	C12—C13—C18	108.09 (19)
C1—C2—C15	108.7 (2)	C17—C13—C18	109.67 (19)
C16—C2—C3	108.65 (19)	C12—C13—C14	111.20 (17)
C1—C2—C3	110.51 (19)	C17—C13—C14	108.9 (2)
C15—C2—C3	108.50 (18)	C18—C13—C14	109.9 (2)
O1—C3—N1	122.32 (19)	C13—C14—H14A	109.5
O1—C3—C2	121.91 (19)	C13—C14—H14B	109.5
N1—C3—C2	115.75 (18)	H14A—C14—H14B	109.5
N2—C4—N1	115.32 (18)	C13—C14—H14C	109.5
N2—C4—S1	125.71 (16)	H14A—C14—H14C	109.5
N1—C4—S1	118.96 (16)	H14B—C14—H14C	109.5
N2—C5—C10	109.84 (16)	C2—C15—H15A	109.5
N2—C5—C6	109.84 (16)	C2—C15—H15B	109.5
C10—C5—C6	111.57 (17)	H15A—C15—H15B	109.5
N2—C5—H5	108.5	C2—C15—H15C	109.5
C10—C5—H5	108.5	H15A—C15—H15C	109.5
C6—C5—H5	108.5	H15B—C15—H15C	109.5
C7—C6—C5	112.79 (17)	C2—C16—H16A	109.5
C7—C6—H6A	109.0	C2—C16—H16B	109.5
C5—C6—H6A	109.0	H16A—C16—H16B	109.5
C7—C6—H6B	109.0	C2—C16—H16C	109.5
C5—C6—H6B	109.0	H16A—C16—H16C	109.5
H6A—C6—H6B	107.8	H16B—C16—H16C	109.5
C8—C7—C6	110.14 (19)	C13—C17—H17A	109.5
C8—C7—H7A	109.6	C13—C17—H17B	109.5
C6—C7—H7A	109.6	H17A—C17—H17B	109.5
C8—C7—H7B	109.6	C13—C17—H17C	109.5
C6—C7—H7B	109.6	H17A—C17—H17C	109.5
H7A—C7—H7B	108.1	H17B—C17—H17C	109.5
C9—C8—C7	110.28 (19)	C13—C18—H18A	109.5
C9—C8—H8A	109.6	C13—C18—H18B	109.5
C7—C8—H8A	109.6	H18A—C18—H18B	109.5
C9—C8—H8B	109.6	C13—C18—H18C	109.5
C7—C8—H8B	109.6	H18A—C18—H18C	109.5
H8A—C8—H8B	108.1	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.97	2.650 (2)	135
N3—H3···O2	0.86	1.99	2.670 (2)	135
N1—H1···O2ⁱ	0.86	2.25	3.078 (2)	161
C1—H1B···O2ⁱ	0.96	2.54	3.462 (3)	161

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₃₂N₄O₂S₂
M_r	400.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.960 (2), 19.065 (4), 10.378 (2)
β (°)	96.112 (4)
V (Å³)	2156.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.48 × 0.41 × 0.37

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.883, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	10928, 3779, 2828
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.124, 1.07
No. of reflections	3779
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	1.97	2.650 (2)	135
N3—H3···O2	0.86	1.99	2.670 (2)	135
N1—H1···O2ⁱ	0.86	2.25	3.078 (2)	161
C1—H1B···O2ⁱ	0.96	2.54	3.462 (3)	161

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Malaysia Terengganu and the Ministry of Higher Education, Malaysia, for research grants OUP UKM OUP-BIT-28/20076 and UMT-FRGS-59001.

References

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