5-[1-(1,3-Dimethyl-2,4,6-trioxohexa­hydropyrimidin-5-yl)-2-oxoprop­yl]-1,3-di­methyl­pyrimidine-2,4,6(1H,3H,5H)-trione

Sweidan, K.; Steimann, M.

doi:10.1107/S1600536813020138

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1334

doi:10.1107/S1600536813020138

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5-[1-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

Kamal Sweidan ^a ^* and Manfred Steimann ^b

^aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan, and ^bInstitut für Anorganische Chemie der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
^*Correspondence e-mail: k.sweidan@ju.edu.jo

(Received 30 April 2013; accepted 21 July 2013; online 27 July 2013)

The title compound, C₁₅H₁₈N₄O₇, is a product of the substitution reaction of 5,5-dibromo-1,3-dimethylbarbituric acid with sodium sulfide in aqueous acetone. In the crystal, molecules display neither intermolecular nor intramolecular hydrogen bonding and the two barbiturate rings adopt the keto form.

Related literature

For general applications of barbituric acid, see: Negwer (2001 ); Bojarski et al. (1985 ); Sans & Chosaz (1988 ). For the structures of related compounds, see: Sweidan et al. (2009 ); Ahadi et al. (2012 ). For the synthesis of the starting material, see: Sweidan et al. (2010 ).

Experimental

Crystal data

C₁₅H₁₈N₄O₇
M_r = 366.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.253 (2) Å
b = 13.179 (3) Å
c = 13.360 (3) Å
V = 1629.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 213 K
0.50 × 0.35 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
1911 measured reflections
1911 independent reflections
1265 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.099
S = 1.07
1911 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1998 ); cell refinement: SET4 and CEKDIM in CAD-4 Software; data reduction: HELENA/PLATON (Spek, 2009 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813020138/mw2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020138/mw2109Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020138/mw2109Isup3.cml

checkCIF report

Comment top

Many 1,3-dimethylbarbituric acid derivatives play important roles in the areas of pharmaceutical and medicinal chemistry (Bojarski et al., 1985; Sans & Chosaz, 1988). In the target molecule, two moieties of the 1,3-dimethylbarbiturate anion were attached to the same carbon of the acetone molecule and hydrogen sulfide and sodium bromide were produced during the course of the reaction. It is clear that each barbiturate ring adopts a keto form rather than the enol form as indicated by the bond angles C1-C2-C3 (116.1 (3)°), C3-C2-C13 (109.1 (2)°) and C1-C2-C13 (115.5 (2)°) for one barbiturate ring and C7-C8-C13 (112.6 (3)°), C9-C8-C13 (114.4 (3)°) and C7-C8-C9 (116.31 (3)°) for the second one. In addition, the bond lengths C12-C13 (153.7 (4) pm) and C13-C8 (154.3 (4) pm) lie within the normal range for a carbon-carbon (sp³-sp³) single bond length. Due to the steric bulk of the barbiturate rings, the bond angle C2-C13-C8 (116.2 (2)°) is noticeably larger than C2-C13-C14 (110.4 (3)°) or C8-C13-C14 (113.0 (3)°).

Related literature top

For general applications of barbituric acid, see: Negwer (2001); Bojarski et al. (1985); Sans & Chosaz (1988). For the structures of related compounds, see: Sweidan et al. (2009); Ahadi et al. (2012). For the synthesis of the starting material, see: Sweidan et al. (2010).

Experimental top

The title compound, C₁₅H₁₈N₄O₇, was prepared by addition of a solution of 5,5-dibromo-1,3-dimethylbarbituric acid (Sweidan et al., 2010), (0.74g, 2.4 mmol) in 10 mL of acetone to a solution of sodium sulfide (0.19g, 2.4 mmol) in 15 mL of water at room temperature. After the reaction mixture was stirred overnight, the precipitate was filtered off and dried in vacuo. The yield after recrystallisation from dichloromethane/diethyl ether was 0.24g (22%) as colorless crystals.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1998); cell refinement: SET4 and CEKDIM in CAD-4 Software (Enraf–Nonius, 1998); data reduction: HELENA/PLATON (Spek, 2009); 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).

Figures top

Fig. 1. The molecular structure of the title molecule showing the atom numbering scheme with 20% probability displacement ellipsoids for non-H atoms.

5-[1-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione top

Crystal data top

C₁₅H₁₈N₄O₇	F(000) = 768
M_r = 366.33	D_x = 1.494 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.253 (2) Å	θ = 6.8–15.5°
b = 13.179 (3) Å	µ = 0.12 mm⁻¹
c = 13.360 (3) Å	T = 213 K
V = 1629.2 (6) Å³	Cube, colourless
Z = 4	0.50 × 0.35 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 26.4°, θ_min = 3.1°
Graphite monochromator	h = 0→11
ω scans	k = 0→16
1911 measured reflections	l = 0→16
1911 independent reflections	3 standard reflections every 200 reflections
1265 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0391P)² + 0.2519P] where P = (F_o² + 2F_c²)/3
1911 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₈N₄O₇	V = 1629.2 (6) Å³
M_r = 366.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.253 (2) Å	µ = 0.12 mm⁻¹
b = 13.179 (3) Å	T = 213 K
c = 13.360 (3) Å	0.50 × 0.35 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
1911 measured reflections	3 standard reflections every 200 reflections
1911 independent reflections	intensity decay: 1.0%
1265 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
1911 reflections	Δρ_min = −0.17 e Å⁻³
240 parameters

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.

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 > 2sigma(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
N1	0.1811 (3)	0.5023 (2)	0.09198 (18)	0.0356 (6)
N2	0.2638 (3)	0.38060 (19)	−0.02592 (18)	0.0375 (7)
N3	0.6557 (3)	0.6949 (2)	0.23141 (19)	0.0404 (7)
N4	0.5211 (3)	0.82117 (18)	0.1472 (2)	0.0397 (7)
O1	0.3230 (3)	0.62919 (18)	0.14586 (18)	0.0551 (7)
O2	0.0383 (3)	0.37348 (19)	0.0384 (2)	0.0646 (8)
O3	0.4834 (3)	0.39452 (18)	−0.09365 (19)	0.0559 (7)
O4	0.7066 (3)	0.54505 (17)	0.15638 (17)	0.0462 (6)
O5	0.5992 (3)	0.84280 (18)	0.30569 (17)	0.0576 (7)
O6	0.4264 (3)	0.79063 (16)	−0.00524 (17)	0.0488 (6)
O7	0.3341 (3)	0.60948 (19)	−0.12316 (17)	0.0517 (7)
C1	0.3085 (4)	0.5526 (2)	0.0950 (2)	0.0374 (8)
C2	0.4327 (3)	0.5085 (2)	0.0391 (2)	0.0347 (8)
H2	0.4939	0.4763	0.0909	0.042*
C3	0.3974 (4)	0.4251 (2)	−0.0330 (2)	0.0388 (8)
C4	0.1547 (4)	0.4153 (2)	0.0347 (2)	0.0382 (8)
C5	0.0635 (4)	0.5370 (3)	0.1582 (2)	0.0512 (10)
H5A	0.0940	0.5312	0.2275	0.077*
H5B	−0.0216	0.4954	0.1474	0.077*
H5C	0.0408	0.6073	0.1434	0.077*
C6	0.2332 (4)	0.2914 (3)	−0.0893 (3)	0.0557 (10)
H6A	0.1466	0.2578	−0.0654	0.084*
H6B	0.3141	0.2447	−0.0861	0.084*
H6C	0.2189	0.3131	−0.1579	0.084*
C7	0.6562 (3)	0.6294 (3)	0.1511 (2)	0.0375 (8)
C8	0.5953 (3)	0.6702 (2)	0.0545 (2)	0.0335 (7)
H8	0.6815	0.6938	0.0173	0.040*
C9	0.5027 (4)	0.7636 (2)	0.0630 (2)	0.0365 (8)
C10	0.5932 (4)	0.7903 (3)	0.2325 (3)	0.0429 (9)
C11	0.7255 (4)	0.6633 (3)	0.3251 (2)	0.0573 (11)
H11A	0.7699	0.5973	0.3159	0.086*
H11B	0.6537	0.6593	0.3778	0.086*
H11C	0.7989	0.7124	0.3434	0.086*
C12	0.4578 (4)	0.9231 (2)	0.1506 (3)	0.0570 (11)
H12A	0.4153	0.9390	0.0862	0.085*
H12B	0.5327	0.9722	0.1660	0.085*
H12C	0.3838	0.9255	0.2019	0.085*
C13	0.5319 (3)	0.5860 (2)	−0.0127 (2)	0.0359 (8)
H13	0.6162	0.5464	−0.0364	0.043*
C14	0.4602 (4)	0.6271 (2)	−0.1071 (2)	0.0410 (8)
C15	0.5562 (4)	0.6769 (3)	−0.1827 (2)	0.0547 (10)
H15A	0.6098	0.6254	−0.2189	0.082*
H15B	0.6232	0.7219	−0.1488	0.082*
H15C	0.4978	0.7157	−0.2292	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0331 (18)	0.0352 (16)	0.0383 (16)	0.0004 (16)	0.0103 (15)	0.0043 (15)
N2	0.0343 (19)	0.0382 (18)	0.0393 (17)	−0.0073 (16)	−0.0013 (15)	−0.0007 (15)
N3	0.038 (2)	0.0413 (18)	0.0420 (16)	−0.0019 (17)	−0.0140 (17)	0.0002 (16)
N4	0.039 (2)	0.0324 (15)	0.0457 (18)	0.0022 (16)	−0.0040 (17)	−0.0023 (15)
O1	0.0511 (19)	0.0493 (18)	0.0644 (17)	−0.0075 (17)	0.0168 (17)	−0.0184 (16)
O2	0.0419 (19)	0.0602 (19)	0.090 (2)	−0.0187 (17)	0.0097 (17)	−0.0099 (17)
O3	0.0493 (19)	0.0521 (16)	0.0664 (18)	−0.0012 (17)	0.0193 (17)	−0.0176 (16)
O4	0.0379 (17)	0.0378 (16)	0.0616 (17)	0.0044 (15)	−0.0089 (15)	0.0006 (14)
O5	0.070 (2)	0.0578 (17)	0.0451 (15)	0.0006 (18)	−0.0025 (17)	−0.0202 (14)
O6	0.0498 (17)	0.0501 (15)	0.0450 (14)	0.0078 (15)	−0.0096 (16)	0.0026 (14)
O7	0.0423 (19)	0.0594 (19)	0.0515 (17)	−0.0092 (17)	−0.0123 (15)	0.0064 (15)
C1	0.038 (2)	0.035 (2)	0.038 (2)	−0.005 (2)	0.0047 (19)	0.0021 (19)
C2	0.026 (2)	0.0382 (19)	0.0401 (19)	0.0016 (18)	0.0017 (18)	0.0050 (17)
C3	0.038 (2)	0.037 (2)	0.038 (2)	0.000 (2)	0.002 (2)	−0.0021 (18)
C4	0.033 (2)	0.038 (2)	0.044 (2)	−0.004 (2)	0.0014 (19)	0.0091 (19)
C5	0.043 (3)	0.054 (2)	0.056 (2)	0.005 (2)	0.021 (2)	0.012 (2)
C6	0.054 (3)	0.049 (2)	0.061 (3)	−0.009 (3)	−0.001 (3)	−0.009 (2)
C7	0.024 (2)	0.038 (2)	0.050 (2)	−0.0038 (19)	−0.0010 (19)	−0.002 (2)
C8	0.025 (2)	0.0350 (19)	0.0419 (19)	−0.0014 (18)	−0.0005 (19)	0.0004 (16)
C9	0.029 (2)	0.039 (2)	0.040 (2)	−0.0013 (19)	−0.0042 (19)	0.0038 (18)
C10	0.037 (2)	0.042 (2)	0.049 (2)	−0.006 (2)	0.003 (2)	0.002 (2)
C11	0.060 (3)	0.059 (3)	0.054 (3)	−0.002 (3)	−0.028 (2)	0.002 (2)
C12	0.064 (3)	0.037 (2)	0.070 (3)	0.011 (2)	−0.003 (3)	−0.005 (2)
C13	0.029 (2)	0.0339 (17)	0.044 (2)	−0.0009 (18)	0.0045 (19)	−0.0019 (17)
C14	0.046 (3)	0.039 (2)	0.036 (2)	−0.006 (2)	0.000 (2)	−0.0030 (17)
C15	0.064 (3)	0.054 (2)	0.045 (2)	−0.016 (3)	0.004 (2)	0.001 (2)

Geometric parameters (Å, º) top

N1—C1	1.354 (4)	C5—H5A	0.9700
N1—C4	1.400 (4)	C5—H5B	0.9700
N1—C5	1.475 (4)	C5—H5C	0.9700
N2—C3	1.371 (4)	C6—H6A	0.9700
N2—C4	1.373 (4)	C6—H6B	0.9700
N2—C6	1.476 (4)	C6—H6C	0.9700
N3—C7	1.377 (4)	C7—C8	1.507 (4)
N3—C10	1.384 (4)	C8—C9	1.504 (4)
N3—C11	1.469 (4)	C8—C13	1.543 (4)
N4—C9	1.368 (4)	C8—H8	0.9900
N4—C10	1.381 (4)	C11—H11A	0.9700
N4—C12	1.466 (4)	C11—H11B	0.9700
O1—C1	1.224 (4)	C11—H11C	0.9700
O2—C4	1.211 (4)	C12—H12A	0.9700
O3—C3	1.206 (4)	C12—H12B	0.9700
O4—C7	1.208 (4)	C12—H12C	0.9700
O5—C10	1.199 (4)	C13—C14	1.525 (4)
O6—C9	1.207 (4)	C13—H13	0.9900
O7—C14	1.209 (4)	C14—C15	1.496 (5)
C1—C2	1.489 (4)	C15—H15A	0.9700
C2—C3	1.498 (4)	C15—H15B	0.9700
C2—C13	1.537 (4)	C15—H15C	0.9700
C2—H2	0.9900

C1—N1—C4	124.7 (3)	N3—C7—C8	116.2 (3)
C1—N1—C5	118.2 (3)	C9—C8—C7	116.1 (3)
C4—N1—C5	117.0 (3)	C9—C8—C13	114.6 (3)
C3—N2—C4	124.1 (3)	C7—C8—C13	112.6 (3)
C3—N2—C6	118.3 (3)	C9—C8—H8	103.9
C4—N2—C6	117.6 (3)	C7—C8—H8	103.9
C7—N3—C10	125.4 (3)	C13—C8—H8	103.9
C7—N3—C11	119.0 (3)	O6—C9—N4	122.1 (3)
C10—N3—C11	115.7 (3)	O6—C9—C8	121.2 (3)
C9—N4—C10	125.1 (3)	N4—C9—C8	116.4 (3)
C9—N4—C12	118.9 (3)	O5—C10—N4	121.7 (3)
C10—N4—C12	115.9 (3)	O5—C10—N3	120.8 (3)
O1—C1—N1	121.1 (3)	N4—C10—N3	117.5 (3)
O1—C1—C2	121.0 (3)	N3—C11—H11A	109.5
N1—C1—C2	117.8 (3)	N3—C11—H11B	109.5
C1—C2—C3	116.1 (3)	H11A—C11—H11B	109.5
C1—C2—C13	115.3 (2)	N3—C11—H11C	109.5
C3—C2—C13	109.1 (2)	H11A—C11—H11C	109.5
C1—C2—H2	105.0	H11B—C11—H11C	109.5
C3—C2—H2	105.0	N4—C12—H12A	109.5
C13—C2—H2	105.0	N4—C12—H12B	109.5
O3—C3—N2	119.9 (3)	H12A—C12—H12B	109.5
O3—C3—C2	122.2 (3)	N4—C12—H12C	109.5
N2—C3—C2	117.8 (3)	H12A—C12—H12C	109.5
O2—C4—N2	121.8 (3)	H12B—C12—H12C	109.5
O2—C4—N1	120.4 (3)	C14—C13—C2	110.4 (3)
N2—C4—N1	117.9 (3)	C14—C13—C8	113.0 (3)
N1—C5—H5A	109.5	C2—C13—C8	116.2 (2)
N1—C5—H5B	109.5	C14—C13—H13	105.4
H5A—C5—H5B	109.5	C2—C13—H13	105.4
N1—C5—H5C	109.5	C8—C13—H13	105.4
H5A—C5—H5C	109.5	O7—C14—C15	122.5 (3)
H5B—C5—H5C	109.5	O7—C14—C13	119.9 (3)
N2—C6—H6A	109.5	C15—C14—C13	117.1 (3)
N2—C6—H6B	109.5	C14—C15—H15A	109.5
H6A—C6—H6B	109.5	C14—C15—H15B	109.5
N2—C6—H6C	109.5	H15A—C15—H15B	109.5
H6A—C6—H6C	109.5	C14—C15—H15C	109.5
H6B—C6—H6C	109.5	H15A—C15—H15C	109.5
O4—C7—N3	122.2 (3)	H15B—C15—H15C	109.5
O4—C7—C8	121.5 (3)

C4—N1—C1—O1	178.9 (3)	O4—C7—C8—C13	30.0 (4)
C5—N1—C1—O1	−5.1 (5)	N3—C7—C8—C13	−152.3 (3)
C4—N1—C1—C2	−4.5 (4)	C10—N4—C9—O6	172.4 (3)
C5—N1—C1—C2	171.5 (3)	C12—N4—C9—O6	−6.2 (5)
O1—C1—C2—C3	−170.6 (3)	C10—N4—C9—C8	−14.2 (5)
N1—C1—C2—C3	12.8 (4)	C12—N4—C9—C8	167.2 (3)
O1—C1—C2—C13	−41.1 (4)	C7—C8—C9—O6	−165.3 (3)
N1—C1—C2—C13	142.3 (3)	C13—C8—C9—O6	−31.3 (4)
C4—N2—C3—O3	−174.4 (3)	C7—C8—C9—N4	21.3 (4)
C6—N2—C3—O3	3.9 (4)	C13—C8—C9—N4	155.2 (3)
C4—N2—C3—C2	8.0 (4)	C9—N4—C10—O5	−176.3 (3)
C6—N2—C3—C2	−173.7 (3)	C12—N4—C10—O5	2.3 (5)
C1—C2—C3—O3	168.0 (3)	C9—N4—C10—N3	2.2 (5)
C13—C2—C3—O3	35.6 (4)	C12—N4—C10—N3	−179.2 (3)
C1—C2—C3—N2	−14.5 (4)	C7—N3—C10—O5	−179.2 (3)
C13—C2—C3—N2	−146.9 (3)	C11—N3—C10—O5	1.1 (5)
C3—N2—C4—O2	179.9 (3)	C7—N3—C10—N4	2.3 (5)
C6—N2—C4—O2	1.6 (5)	C11—N3—C10—N4	−177.3 (3)
C3—N2—C4—N1	0.8 (4)	C1—C2—C13—C14	−75.7 (3)
C6—N2—C4—N1	−177.5 (3)	C3—C2—C13—C14	57.1 (3)
C1—N1—C4—O2	178.2 (3)	C1—C2—C13—C8	54.7 (4)
C5—N1—C4—O2	2.2 (4)	C3—C2—C13—C8	−172.4 (3)
C1—N1—C4—N2	−2.8 (4)	C9—C8—C13—C14	40.2 (4)
C5—N1—C4—N2	−178.7 (3)	C7—C8—C13—C14	175.8 (3)
C10—N3—C7—O4	−176.3 (3)	C9—C8—C13—C2	−89.0 (3)
C11—N3—C7—O4	3.3 (5)	C7—C8—C13—C2	46.6 (4)
C10—N3—C7—C8	5.9 (4)	C2—C13—C14—O7	11.0 (4)
C11—N3—C7—C8	−174.4 (3)	C8—C13—C14—O7	−121.2 (3)
O4—C7—C8—C9	164.9 (3)	C2—C13—C14—C15	−161.4 (3)
N3—C7—C8—C9	−17.4 (4)	C8—C13—C14—C15	66.5 (4)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₄O₇
M_r	366.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	213
a, b, c (Å)	9.253 (2), 13.179 (3), 13.360 (3)
V (Å³)	1629.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.50 × 0.35 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1911, 1911, 1265
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.099, 1.07
No. of reflections	1911
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: , SET4 and CEKDIM in CAD-4 Software (Enraf–Nonius, 1998), HELENA/PLATON (Spek, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

KS gratefully acknowledges financial support from the Deanship of Scientific Research at the University of Jordan.

References

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