Ethyl 4-acetyl-5-anilino-3-methyl­thio­phene-2-carboxyl­ate

Mabkhot, Y.N.; Alatibi, F.; Barakat, A.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S160053681301547X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1049

https://doi.org/10.1107/S160053681301547X

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Ethyl 4-acetyl-5-anilino-3-methylthiophene-2-carboxylate

Yahia Nasser Mabkhot,^a ‡ Fatima Alatibi,^a Assem Barakat,^a,^b M. Iqbal Choudhary ^c,^a and Sammer Yousuf ^c ^*

^aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia 21321 Alexandria, Egypt, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 28 May 2013; accepted 4 June 2013; online 8 June 2013)

In the title compound, C₁₆H₁₇NO₃S, a thiophene derivative with amino phenyl, acetyl, methyl and ethyl carboxyl susbtituents attached to a central thiophene ring, the phenyl and thiophene rings form a dihedral angle of 36.92 (9) Å. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, which forms an S(6) ring motif.

Related literature

For the biological activity of thiophene derivatives, see: Mishra et al. (2011 ); Mabkhot et al. (2013b ). For the synthesis of fused heterocyclic compounds, see: Sommen et al. (2003 ). For crystal data for related thiophene compounds, see: Mabkhot et al. (2013a ,b); Buehrdel et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₇NO₃S
M_r = 303.37
Triclinic, $[P \overline 1]$
a = 7.9443 (6) Å
b = 9.5038 (7) Å
c = 11.8706 (9) Å
α = 66.759 (2)°
β = 89.754 (2)°
γ = 66.785 (2)°
V = 744.60 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 273 K
0.45 × 0.42 × 0.23 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.905, T_max = 0.950
10410 measured reflections
3699 independent reflections
2848 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.05
3699 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.82 (3)	1.93 (3)	2.607 (3)	140 (2)

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; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681301547X/rz5071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681301547X/rz5071Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681301547X/rz5071Isup3.cml

checkCIF report

Comment top

Sulfur containing heterocyclic compounds are well known for their diverse range of biological activities (Mabkhot et al., 2013b; Mishra et al. 2011). The title compound was synthesized in continuation of our research towards the synthesis of biologically active compounds with fused heterocyclic systems (Mabkhot et al., 2013b).

The structure of the title compound (Fig. 1) is composed of a planar thiophene (S1/C2–C5) ring with amino phenyl (N1/C12–C17), acetyl (O1/C10–C11), methyl (C8) and ethyl carboxylate (O2–O3/N2/C6–C7) susbtituents attached to atoms C1, C2,C3 and C4, respectively, of the thiophene ring. The dihedral angle between the planes of thiophene and amino phenyl ring (N1/C11–C16) is 36.92 (9)°. The bond lengths and angles are similar to those of structurally related compounds (Mabkhot et al., 2013a,b; Buehrdel et al., 2007). The molecular conformation is stabilized by an N1—H1A···O1 intramolecular hydrogen bond (Table 1) to form a S6 graph set ring motif. In the crystal packing (Fig. 2), no π···π or C—H···π interactions are observed between adjacent molecules.

Related literature top

For the biological activity of thiophene derivatives, see: Mishra et al. (2011); Mabkhot et al. (2013b). For the synthesis of fused heterocyclic compounds, see: Sommen et al. (2003). For crystal data for related thiophene compounds, see: Mabkhot et al. (2013a,b); Buehrdel et al. (2007).

Experimental top

The title compound was synthesized by the procedure described in the literature (Sommen et al., 2003). The compound was crystallized by using a mixture of dimethyl formamide and dichloromethane 1:1 v/v at room temperature. M. p.: 399 K. Spectral Data: IR (KBr, cm^-1): 1680, 1700, 2990 cm^-1; ¹H-NMR (400 MHz, CDCl₃): δ 1.34 (t, 3H, J = 7.1 Hz), 2.58 (s, 3H), 2.82 (s, 3H), 4.28 (q, 2H, J = 7.1 Hz), 7.35–7.42 (m, 5H), 12.1 (s, 1H); ¹³C-NMR (100 MHz, CDCl₃): δ 14.3, 16.5, 31.3, 60.5, 108.9, 119.2, 120.5, 124.7 (2 C), 129.5 (2 C), 139.6, 145.8, 162.7, 163.4, 195.7; Anal. calcd for C₁₆H₁₇NO₃S: C 63.34; H 5.65; N 4.62. Found: C 63.47; H 5.46; N 4.61.

Structure description top

For the biological activity of thiophene derivatives, see: Mishra et al. (2011); Mabkhot et al. (2013b). For the synthesis of fused heterocyclic compounds, see: Sommen et al. (2003). For crystal data for related thiophene compounds, see: Mabkhot et al. (2013a,b); Buehrdel et al. (2007).

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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. Crystal packing of the title compound viewed down the b axis. Hydrogen atoms are ommited for clarity.

Ethyl 4-acetyl-5-anilino-3-methylthiophene-2-carboxylate top

Crystal data top

C₁₆H₁₇NO₃S	Z = 2
M_r = 303.37	F(000) = 320
Triclinic, P1	D_x = 1.353 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9443 (6) Å	Cell parameters from 2619 reflections
b = 9.5038 (7) Å	θ = 2.5–25.8°
c = 11.8706 (9) Å	µ = 0.23 mm⁻¹
α = 66.759 (2)°	T = 273 K
β = 89.754 (2)°	Block, yellow
γ = 66.785 (2)°	0.45 × 0.42 × 0.23 mm
V = 744.60 (10) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	2848 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scan	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.905, T_max = 0.950	k = −12→12
10410 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0618P)² + 0.0954P] where P = (F_o² + 2F_c²)/3
3699 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₇NO₃S	γ = 66.785 (2)°
M_r = 303.37	V = 744.60 (10) Å³
Triclinic, P1	Z = 2
a = 7.9443 (6) Å	Mo Kα radiation
b = 9.5038 (7) Å	µ = 0.23 mm⁻¹
c = 11.8706 (9) Å	T = 273 K
α = 66.759 (2)°	0.45 × 0.42 × 0.23 mm
β = 89.754 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3699 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2848 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.950	R_int = 0.028
10410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.30 e Å⁻³
3699 reflections	Δρ_min = −0.25 e Å⁻³
194 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	0.48333 (6)	0.26835 (5)	−0.00730 (4)	0.04325 (15)
O1	0.8347 (2)	0.01329 (18)	−0.22852 (13)	0.0685 (4)
O2	0.6413 (2)	−0.06433 (17)	0.34080 (12)	0.0704 (5)
O3	0.41944 (19)	0.19842 (16)	0.23323 (11)	0.0546 (3)
N1	0.5630 (2)	0.2832 (2)	−0.23190 (14)	0.0483 (4)
C2	0.6046 (2)	0.1930 (2)	−0.10687 (15)	0.0404 (4)
C3	0.7453 (2)	0.0270 (2)	−0.04358 (15)	0.0407 (4)
C4	0.7482 (2)	−0.0370 (2)	0.08869 (15)	0.0394 (4)
C5	0.6149 (2)	0.0774 (2)	0.12066 (15)	0.0419 (4)
C6	0.5653 (3)	0.0580 (2)	0.24344 (16)	0.0475 (4)
C7	0.3506 (3)	0.1937 (3)	0.34727 (19)	0.0634 (6)
H7A	0.4503	0.1639	0.4111	0.076*
H7B	0.2996	0.1109	0.3776	0.076*
C8	0.2028 (3)	0.3670 (3)	0.3158 (2)	0.0728 (6)
H8A	0.1526	0.3702	0.3889	0.109*
H8B	0.1054	0.3948	0.2524	0.109*
H8C	0.2553	0.4475	0.2858	0.109*
C9	0.8800 (3)	−0.2083 (2)	0.18489 (17)	0.0539 (5)
H9A	0.8528	−0.2197	0.2661	0.081*
H9B	1.0055	−0.2205	0.1820	0.081*
H9C	0.8659	−0.2944	0.1682	0.081*
C10	0.8559 (2)	−0.0600 (2)	−0.11438 (17)	0.0466 (4)
C11	0.9989 (3)	−0.2421 (3)	−0.0534 (2)	0.0605 (5)
H11A	1.0558	−0.2749	−0.1159	0.091*
H11B	0.9394	−0.3133	−0.0102	0.091*
H11C	1.0925	−0.2538	0.0049	0.091*
C12	0.4166 (2)	0.4428 (2)	−0.30492 (15)	0.0435 (4)
C13	0.3570 (3)	0.5761 (2)	−0.27179 (18)	0.0536 (5)
H13A	0.4097	0.5614	−0.1958	0.064*
C14	0.2190 (3)	0.7316 (2)	−0.3516 (2)	0.0640 (6)
H14A	0.1781	0.8210	−0.3286	0.077*
C15	0.1418 (3)	0.7551 (3)	−0.4643 (2)	0.0665 (6)
H15A	0.0501	0.8603	−0.5181	0.080*
C16	0.2008 (3)	0.6224 (3)	−0.49714 (19)	0.0653 (6)
H16A	0.1484	0.6380	−0.5735	0.078*
C17	0.3366 (3)	0.4667 (2)	−0.41818 (17)	0.0540 (5)
H17A	0.3750	0.3772	−0.4409	0.065*
H1A	0.627 (3)	0.228 (3)	−0.267 (2)	0.058 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0447 (3)	0.0347 (2)	0.0357 (2)	−0.00843 (18)	0.00177 (18)	−0.00958 (17)
O1	0.0810 (10)	0.0576 (9)	0.0452 (8)	−0.0093 (8)	0.0116 (7)	−0.0217 (7)
O2	0.0924 (11)	0.0462 (8)	0.0366 (7)	−0.0056 (7)	0.0057 (7)	−0.0072 (6)
O3	0.0653 (8)	0.0428 (7)	0.0390 (7)	−0.0107 (6)	0.0109 (6)	−0.0139 (6)
N1	0.0532 (9)	0.0401 (8)	0.0330 (8)	−0.0071 (7)	0.0017 (7)	−0.0105 (6)
C2	0.0419 (9)	0.0394 (9)	0.0344 (8)	−0.0161 (7)	0.0013 (7)	−0.0119 (7)
C3	0.0382 (9)	0.0379 (8)	0.0387 (9)	−0.0121 (7)	0.0011 (7)	−0.0136 (7)
C4	0.0379 (8)	0.0348 (8)	0.0369 (8)	−0.0121 (7)	−0.0019 (7)	−0.0105 (7)
C5	0.0459 (9)	0.0357 (8)	0.0331 (8)	−0.0132 (7)	−0.0013 (7)	−0.0084 (7)
C6	0.0573 (11)	0.0370 (9)	0.0381 (9)	−0.0144 (8)	0.0025 (8)	−0.0121 (7)
C7	0.0785 (15)	0.0569 (12)	0.0454 (11)	−0.0198 (11)	0.0207 (10)	−0.0223 (10)
C8	0.0731 (15)	0.0667 (14)	0.0759 (16)	−0.0192 (12)	0.0235 (13)	−0.0386 (13)
C9	0.0515 (11)	0.0418 (10)	0.0426 (10)	−0.0044 (8)	−0.0029 (8)	−0.0090 (8)
C10	0.0447 (10)	0.0452 (10)	0.0461 (10)	−0.0156 (8)	0.0045 (8)	−0.0194 (8)
C11	0.0581 (12)	0.0510 (11)	0.0601 (13)	−0.0085 (9)	0.0104 (10)	−0.0268 (10)
C12	0.0440 (9)	0.0390 (9)	0.0351 (9)	−0.0153 (7)	0.0041 (7)	−0.0065 (7)
C13	0.0664 (13)	0.0430 (10)	0.0415 (10)	−0.0210 (9)	−0.0020 (9)	−0.0107 (8)
C14	0.0776 (15)	0.0396 (10)	0.0563 (13)	−0.0154 (10)	0.0040 (11)	−0.0126 (9)
C15	0.0637 (13)	0.0466 (11)	0.0528 (12)	−0.0064 (10)	−0.0046 (10)	−0.0034 (9)
C16	0.0684 (14)	0.0613 (13)	0.0417 (11)	−0.0148 (11)	−0.0086 (10)	−0.0112 (10)
C17	0.0619 (12)	0.0493 (10)	0.0368 (10)	−0.0146 (9)	0.0011 (8)	−0.0140 (8)

Geometric parameters (Å, º) top

S1—C2	1.7182 (18)	C8—H8C	0.9600
S1—C5	1.7422 (16)	C9—H9A	0.9600
O1—C10	1.230 (2)	C9—H9B	0.9600
O2—C6	1.202 (2)	C9—H9C	0.9600
O3—C6	1.339 (2)	C10—C11	1.509 (3)
O3—C7	1.449 (2)	C11—H11A	0.9600
N1—C2	1.350 (2)	C11—H11B	0.9600
N1—C12	1.409 (2)	C11—H11C	0.9600
N1—H1A	0.82 (2)	C12—C13	1.379 (3)
C2—C3	1.409 (2)	C12—C17	1.384 (3)
C3—C4	1.439 (2)	C13—C14	1.382 (3)
C3—C10	1.460 (2)	C13—H13A	0.9300
C4—C5	1.365 (2)	C14—C15	1.371 (3)
C4—C9	1.500 (2)	C14—H14A	0.9300
C5—C6	1.468 (2)	C15—C16	1.372 (3)
C7—C8	1.491 (3)	C15—H15A	0.9300
C7—H7A	0.9700	C16—C17	1.374 (3)
C7—H7B	0.9700	C16—H16A	0.9300
C8—H8A	0.9600	C17—H17A	0.9300
C8—H8B	0.9600

C2—S1—C5	91.06 (8)	C4—C9—H9B	109.5
C6—O3—C7	116.03 (14)	H9A—C9—H9B	109.5
C2—N1—C12	129.39 (17)	C4—C9—H9C	109.5
C2—N1—H1A	111.3 (15)	H9A—C9—H9C	109.5
C12—N1—H1A	118.8 (15)	H9B—C9—H9C	109.5
N1—C2—C3	124.72 (16)	O1—C10—C3	120.70 (17)
N1—C2—S1	122.77 (13)	O1—C10—C11	116.71 (17)
C3—C2—S1	112.47 (12)	C3—C10—C11	122.59 (17)
C2—C3—C4	111.16 (15)	C10—C11—H11A	109.5
C2—C3—C10	119.78 (15)	C10—C11—H11B	109.5
C4—C3—C10	128.91 (15)	H11A—C11—H11B	109.5
C5—C4—C3	112.44 (14)	C10—C11—H11C	109.5
C5—C4—C9	121.66 (16)	H11A—C11—H11C	109.5
C3—C4—C9	125.89 (16)	H11B—C11—H11C	109.5
C4—C5—C6	129.30 (15)	C13—C12—C17	119.32 (16)
C4—C5—S1	112.85 (13)	C13—C12—N1	123.40 (16)
C6—C5—S1	117.80 (13)	C17—C12—N1	117.20 (17)
O2—C6—O3	123.37 (17)	C12—C13—C14	119.95 (18)
O2—C6—C5	126.39 (17)	C12—C13—H13A	120.0
O3—C6—C5	110.24 (14)	C14—C13—H13A	120.0
O3—C7—C8	106.38 (17)	C15—C14—C13	120.5 (2)
O3—C7—H7A	110.5	C15—C14—H14A	119.8
C8—C7—H7A	110.5	C13—C14—H14A	119.8
O3—C7—H7B	110.5	C14—C15—C16	119.61 (19)
C8—C7—H7B	110.5	C14—C15—H15A	120.2
H7A—C7—H7B	108.6	C16—C15—H15A	120.2
C7—C8—H8A	109.5	C15—C16—C17	120.50 (19)
C7—C8—H8B	109.5	C15—C16—H16A	119.7
H8A—C8—H8B	109.5	C17—C16—H16A	119.7
C7—C8—H8C	109.5	C16—C17—C12	120.15 (19)
H8A—C8—H8C	109.5	C16—C17—H17A	119.9
H8B—C8—H8C	109.5	C12—C17—H17A	119.9
C4—C9—H9A	109.5

C12—N1—C2—C3	174.03 (18)	C4—C5—C6—O2	3.2 (3)
C12—N1—C2—S1	−3.6 (3)	S1—C5—C6—O2	−179.74 (17)
C5—S1—C2—N1	176.62 (16)	C4—C5—C6—O3	−176.76 (17)
C5—S1—C2—C3	−1.28 (14)	S1—C5—C6—O3	0.3 (2)
N1—C2—C3—C4	−176.94 (17)	C6—O3—C7—C8	174.54 (18)
S1—C2—C3—C4	0.91 (19)	C2—C3—C10—O1	4.0 (3)
N1—C2—C3—C10	−1.0 (3)	C4—C3—C10—O1	179.20 (18)
S1—C2—C3—C10	176.89 (13)	C2—C3—C10—C11	−175.38 (17)
C2—C3—C4—C5	0.1 (2)	C4—C3—C10—C11	−0.2 (3)
C10—C3—C4—C5	−175.39 (17)	C2—N1—C12—C13	39.8 (3)
C2—C3—C4—C9	−179.55 (16)	C2—N1—C12—C17	−143.5 (2)
C10—C3—C4—C9	4.9 (3)	C17—C12—C13—C14	−0.1 (3)
C3—C4—C5—C6	176.08 (18)	N1—C12—C13—C14	176.61 (18)
C9—C4—C5—C6	−4.2 (3)	C12—C13—C14—C15	−0.7 (3)
C3—C4—C5—S1	−1.09 (19)	C13—C14—C15—C16	0.8 (4)
C9—C4—C5—S1	178.60 (14)	C14—C15—C16—C17	−0.2 (4)
C2—S1—C5—C4	1.37 (14)	C15—C16—C17—C12	−0.6 (3)
C2—S1—C5—C6	−176.16 (15)	C13—C12—C17—C16	0.7 (3)
C7—O3—C6—O2	−2.5 (3)	N1—C12—C17—C16	−176.19 (19)
C7—O3—C6—C5	177.47 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (3)	1.93 (3)	2.607 (3)	140 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₃S
M_r	303.37
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	7.9443 (6), 9.5038 (7), 11.8706 (9)
α, β, γ (°)	66.759 (2), 89.754 (2), 66.785 (2)
V (Å³)	744.60 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.45 × 0.42 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.905, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	10410, 3699, 2848
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.05
No. of reflections	3699
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.82 (3)	1.93 (3)	2.607 (3)	140 (2)

Footnotes

‡Additional correspondence author, email: yahia@ksu.edu.sa.

Acknowledgements

The authors are thankful to King Saud University, Deanship of Scientific Research, College of Science Research Center, for financial support of this project.

References

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