2-(4-Meth­oxy­phen­yl)-4-oxo-4-phenyl­butane­nitrile

Abdel-Aziz, A.A.-M.; El-Azab, A.S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006290

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o737

doi:10.1107/S1600536812006290

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2-(4-Methoxyphenyl)-4-oxo-4-phenylbutanenitrile

Alaa A.-M. Abdel-Aziz,^a,^b ‡ Adel S. El-Azab,^a,^c Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 13 February 2012; online 17 February 2012)

The title molecule, C₁₇H₁₅NO₂, is twisted, the dihedral angle between the terminal benzene rings being 63.30 (6)°. In the crystal, C—H⋯O and C—H⋯N interactions lead to supramolecular layers in the ab plane. These are connected along the c axis via C—H⋯π interactions.

Related literature

For background to the synthetic applications of 2,4-diaryl-4-oxo-butanenitriles, see: Coudert et al. (1990 ), 1988 ); Iida et al. (2007 ). For the preparation of the title compound, see: Coudert et al. (1990). For the structure of the unsubstituted parent compound, see: Abdel-Aziz et al. (2012 ).

Experimental

Crystal data

C₁₇H₁₅NO₂
M_r = 265.30
Orthorhombic, P b c a
a = 9.5730 (2) Å
b = 8.7748 (2) Å
c = 32.0620 (7) Å
V = 2693.25 (10) Å³
Z = 8
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.651, T_max = 1.000
6569 measured reflections
2764 independent reflections
2410 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 1.02
2764 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8b⋯O1ⁱ	0.99	2.44	3.3102 (16)	147
C15—H15⋯N1ⁱⁱ	0.95	2.62	3.4250 (17)	143
C4—H4⋯Cgⁱⁱⁱ	0.95	2.82	3.5787 (14)	138
C17—H17c⋯Cg^iv	0.98	2.89	3.6754 (15)	138
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006290/xu5470sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006290/xu5470Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006290/xu5470Isup3.cml

checkCIF report

Comment top

An important class of difunctional intermediates for both the synthesis of biologically active heterocycles, such as pyridazine derivatives, and as a source ketone (Coudert et al., 1990; Coudert et al., 1988; Iida et al., 2007) are the 2,4-diaryl-4-oxo-butanenitriles. Herein, the crystal structure of a 2,4-diaryl-4-oxo-butanenitrile derivative, 4-(4-methoxyphenyl)-4-oxo-2-phenylbutanenitrile (I), is described. The structure of the parent compound is known (Abdel-Aziz et al., 2012).

In (I), Fig. 1, the terminal benzene rings form a dihedral angle of 63.30 (6)° indicating a considerable twist in the molecule. The benzyl group is twisted out of the plane of the benzene ring to which it is connected [the C2—C1—C7—C8 torsion angle is -8.58 (17)°] and in addition there is a twist around the C8—C9 bond [the C7—C8—C9—C11 torsion angle is 173.19 (10)°]. The methoxy group is co-planar with the benzene ring to which it is connected [the C17—O2—C14—C13 torsion angle is 3.03 (17)°].

In the crystal packing, molecules are linked by C—H···O and C—H···N interactions into supramolecular layers in the ab plane, Fig. 2 and Table 1. Layers are connected along the c axis via C—H···π interactions involving the (C11–C16) ring, Fig. 3 and Table 1.

Related literature top

For background to the synthetic applications of 2,4-diaryl-4-oxo-butanenitriles, see: Coudert et al. (1990), 1988); Iida et al. (2007). For the preparation of the title compound, see: Coudert et al. (1990). For the structure of the unsubstituted parent compound, see: Abdel-Aziz et al. (2012).

Experimental top

Acetone cyanohydrin (0.045 mol) and 10% aqueous sodium carbonate (0.0015 mol and 1.5 ml water) were added to solution of 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (0.015 mol) in ethanol (50 ml). The mixture was heated at reflux temperature for 4 h. After cooling, the product which separated out was filtered off and recrystallized from methanol solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular array in the ab plane in (I). The C—H···O and C—H···N interactions are shown as orange and blue dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the unit-cell contents for (I). The C—H···O, C—H···N and C—H···π interactions are shown as orange, blue and purple dashed lines, respectively.

2-(4-Methoxyphenyl)-4-oxo-4-phenylbutanenitrile top

Crystal data top

C₁₇H₁₅NO₂	F(000) = 1120
M_r = 265.30	D_x = 1.309 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2587 reflections
a = 9.5730 (2) Å	θ = 2.8–76.0°
b = 8.7748 (2) Å	µ = 0.69 mm⁻¹
c = 32.0620 (7) Å	T = 100 K
V = 2693.25 (10) Å³	Prism, colourless
Z = 8	0.30 × 0.30 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2764 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2410 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.019
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.2°, θ_min = 2.8°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −10→10
T_min = 0.651, T_max = 1.000	l = −33→39
6569 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0514P)² + 0.8432P] where P = (F_o² + 2F_c²)/3
2764 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₅NO₂	V = 2693.25 (10) Å³
M_r = 265.30	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 9.5730 (2) Å	µ = 0.69 mm⁻¹
b = 8.7748 (2) Å	T = 100 K
c = 32.0620 (7) Å	0.30 × 0.30 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2764 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2410 reflections with I > 2σ(I)
T_min = 0.651, T_max = 1.000	R_int = 0.019
6569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
2764 reflections	Δρ_min = −0.21 e Å⁻³
181 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
O1	0.27711 (10)	0.07603 (11)	0.68494 (3)	0.0294 (2)
O2	0.65190 (10)	0.70231 (10)	0.52150 (3)	0.0267 (2)
N1	0.49228 (12)	−0.01483 (13)	0.60258 (3)	0.0282 (3)
C1	0.37272 (13)	0.18133 (13)	0.74651 (4)	0.0214 (3)
C2	0.47344 (13)	0.27465 (14)	0.76484 (4)	0.0235 (3)
H2	0.5322	0.3358	0.7478	0.028*
C3	0.48802 (14)	0.27836 (15)	0.80803 (4)	0.0261 (3)
H3	0.5570	0.3418	0.8204	0.031*
C4	0.40215 (14)	0.18967 (15)	0.83309 (4)	0.0262 (3)
H4	0.4124	0.1922	0.8625	0.031*
C5	0.30090 (14)	0.09693 (15)	0.81498 (4)	0.0268 (3)
H5	0.2420	0.0364	0.8321	0.032*
C6	0.28593 (13)	0.09281 (15)	0.77198 (4)	0.0244 (3)
H6	0.2165	0.0297	0.7598	0.029*
C7	0.35473 (13)	0.17095 (14)	0.70034 (4)	0.0225 (3)
C8	0.43447 (13)	0.28103 (14)	0.67269 (4)	0.0231 (3)
H8A	0.5359	0.2687	0.6777	0.028*
H8B	0.4086	0.3868	0.6802	0.028*
C9	0.40397 (13)	0.25499 (14)	0.62604 (4)	0.0228 (3)
H9	0.3005	0.2589	0.6220	0.027*
C10	0.45287 (13)	0.10206 (15)	0.61327 (4)	0.0230 (3)
C11	0.46935 (13)	0.37597 (14)	0.59828 (4)	0.0222 (3)
C12	0.38502 (13)	0.48068 (15)	0.57791 (4)	0.0251 (3)
H12	0.2867	0.4759	0.5816	0.030*
C13	0.44116 (14)	0.59264 (15)	0.55215 (4)	0.0252 (3)
H13	0.3818	0.6640	0.5386	0.030*
C14	0.58517 (14)	0.59909 (14)	0.54638 (4)	0.0219 (3)
C15	0.67095 (13)	0.49409 (14)	0.56660 (4)	0.0230 (3)
H15	0.7693	0.4985	0.5628	0.028*
C16	0.61369 (13)	0.38362 (14)	0.59212 (4)	0.0233 (3)
H16	0.6730	0.3122	0.6056	0.028*
C17	0.56675 (16)	0.81515 (16)	0.50178 (4)	0.0293 (3)
H17A	0.6249	0.8788	0.4836	0.044*
H17B	0.5226	0.8790	0.5231	0.044*
H17C	0.4944	0.7650	0.4851	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0261 (5)	0.0329 (5)	0.0292 (5)	−0.0061 (4)	0.0019 (4)	−0.0041 (4)
O2	0.0286 (5)	0.0262 (5)	0.0254 (4)	0.0001 (4)	0.0000 (4)	0.0033 (4)
N1	0.0313 (6)	0.0268 (6)	0.0264 (5)	−0.0021 (5)	0.0035 (5)	−0.0028 (4)
C1	0.0201 (6)	0.0188 (6)	0.0252 (6)	0.0040 (5)	0.0029 (5)	0.0002 (4)
C2	0.0228 (6)	0.0201 (6)	0.0276 (6)	0.0005 (5)	0.0042 (5)	0.0007 (5)
C3	0.0250 (6)	0.0240 (6)	0.0294 (6)	0.0010 (5)	−0.0003 (5)	−0.0027 (5)
C4	0.0283 (6)	0.0264 (7)	0.0239 (6)	0.0055 (5)	0.0015 (5)	0.0021 (5)
C5	0.0247 (6)	0.0264 (6)	0.0294 (6)	0.0027 (5)	0.0066 (5)	0.0053 (5)
C6	0.0203 (6)	0.0220 (6)	0.0309 (6)	0.0003 (5)	0.0023 (5)	0.0004 (5)
C7	0.0188 (5)	0.0213 (6)	0.0274 (6)	0.0032 (5)	0.0024 (5)	−0.0028 (5)
C8	0.0235 (6)	0.0227 (6)	0.0232 (6)	0.0008 (5)	0.0013 (5)	−0.0022 (5)
C9	0.0204 (6)	0.0239 (6)	0.0241 (6)	0.0012 (5)	−0.0005 (5)	−0.0009 (5)
C10	0.0227 (6)	0.0268 (7)	0.0197 (5)	−0.0034 (5)	0.0005 (5)	−0.0003 (5)
C11	0.0234 (6)	0.0236 (6)	0.0197 (5)	0.0014 (5)	−0.0005 (5)	−0.0029 (5)
C12	0.0202 (6)	0.0281 (7)	0.0269 (6)	0.0029 (5)	−0.0003 (5)	−0.0013 (5)
C13	0.0255 (6)	0.0255 (6)	0.0246 (6)	0.0048 (5)	−0.0035 (5)	0.0000 (5)
C14	0.0263 (6)	0.0208 (6)	0.0186 (5)	−0.0005 (5)	−0.0001 (5)	−0.0028 (4)
C15	0.0193 (6)	0.0260 (6)	0.0237 (6)	0.0015 (5)	−0.0010 (5)	−0.0041 (5)
C16	0.0235 (6)	0.0238 (6)	0.0225 (6)	0.0043 (5)	−0.0032 (5)	−0.0023 (5)
C17	0.0375 (7)	0.0271 (7)	0.0233 (6)	0.0032 (6)	−0.0012 (5)	0.0035 (5)

Geometric parameters (Å, º) top

O1—C7	1.2205 (15)	C8—H8A	0.9900
O2—C14	1.3656 (15)	C8—H8B	0.9900
O2—C17	1.4299 (15)	C9—C10	1.4791 (17)
N1—C10	1.1454 (17)	C9—C11	1.5201 (17)
C1—C2	1.3949 (17)	C9—H9	1.0000
C1—C6	1.4002 (17)	C11—C12	1.3865 (17)
C1—C7	1.4931 (17)	C11—C16	1.3975 (18)
C2—C3	1.3921 (18)	C12—C13	1.3915 (18)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.3881 (18)	C13—C14	1.3920 (18)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3924 (19)	C14—C15	1.3941 (17)
C4—H4	0.9500	C15—C16	1.3818 (18)
C5—C6	1.3865 (18)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9800
C7—C8	1.5172 (17)	C17—H17B	0.9800
C8—C9	1.5409 (16)	C17—H17C	0.9800

C14—O2—C17	116.80 (10)	C11—C9—C8	112.75 (10)
C2—C1—C6	119.34 (11)	C10—C9—H9	108.0
C2—C1—C7	122.23 (11)	C11—C9—H9	108.0
C6—C1—C7	118.43 (11)	C8—C9—H9	108.0
C3—C2—C1	120.14 (12)	N1—C10—C9	178.38 (13)
C3—C2—H2	119.9	C12—C11—C16	118.50 (12)
C1—C2—H2	119.9	C12—C11—C9	119.93 (11)
C4—C3—C2	120.21 (12)	C16—C11—C9	121.57 (11)
C4—C3—H3	119.9	C11—C12—C13	121.51 (12)
C2—C3—H3	119.9	C11—C12—H12	119.2
C3—C4—C5	119.91 (12)	C13—C12—H12	119.2
C3—C4—H4	120.0	C14—C13—C12	119.34 (12)
C5—C4—H4	120.0	C14—C13—H13	120.3
C6—C5—C4	120.12 (12)	C12—C13—H13	120.3
C6—C5—H5	119.9	O2—C14—C13	124.60 (11)
C4—C5—H5	119.9	O2—C14—C15	115.75 (11)
C5—C6—C1	120.28 (12)	C13—C14—C15	119.65 (12)
C5—C6—H6	119.9	C16—C15—C14	120.35 (12)
C1—C6—H6	119.9	C16—C15—H15	119.8
O1—C7—C1	120.86 (11)	C14—C15—H15	119.8
O1—C7—C8	120.30 (11)	C15—C16—C11	120.64 (12)
C1—C7—C8	118.85 (11)	C15—C16—H16	119.7
C7—C8—C9	112.17 (10)	C11—C16—H16	119.7
C7—C8—H8A	109.2	O2—C17—H17A	109.5
C9—C8—H8A	109.2	O2—C17—H17B	109.5
C7—C8—H8B	109.2	H17A—C17—H17B	109.5
C9—C8—H8B	109.2	O2—C17—H17C	109.5
H8A—C8—H8B	107.9	H17A—C17—H17C	109.5
C10—C9—C11	109.95 (10)	H17B—C17—H17C	109.5
C10—C9—C8	110.08 (10)

C6—C1—C2—C3	0.58 (18)	C10—C9—C11—C12	126.52 (12)
C7—C1—C2—C3	−178.79 (11)	C8—C9—C11—C12	−110.23 (13)
C1—C2—C3—C4	−0.23 (19)	C10—C9—C11—C16	−52.54 (15)
C2—C3—C4—C5	−0.13 (19)	C8—C9—C11—C16	70.70 (15)
C3—C4—C5—C6	0.13 (19)	C16—C11—C12—C13	−0.69 (18)
C4—C5—C6—C1	0.23 (19)	C9—C11—C12—C13	−179.78 (11)
C2—C1—C6—C5	−0.58 (18)	C11—C12—C13—C14	0.55 (19)
C7—C1—C6—C5	178.81 (11)	C17—O2—C14—C13	3.03 (17)
C2—C1—C7—O1	171.59 (11)	C17—O2—C14—C15	−177.49 (10)
C6—C1—C7—O1	−7.78 (17)	C12—C13—C14—O2	179.13 (11)
C2—C1—C7—C8	−8.58 (17)	C12—C13—C14—C15	−0.33 (18)
C6—C1—C7—C8	172.05 (11)	O2—C14—C15—C16	−179.24 (10)
O1—C7—C8—C9	−0.11 (16)	C13—C14—C15—C16	0.27 (18)
C1—C7—C8—C9	−179.94 (10)	C14—C15—C16—C11	−0.42 (18)
C7—C8—C9—C10	−63.64 (13)	C12—C11—C16—C15	0.62 (18)
C7—C8—C9—C11	173.19 (10)	C9—C11—C16—C15	179.70 (11)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8b···O1ⁱ	0.99	2.44	3.3102 (16)	147
C15—H15···N1ⁱⁱ	0.95	2.62	3.4250 (17)	143
C4—H4···Cgⁱⁱⁱ	0.95	2.82	3.5787 (14)	138
C17—H17c···Cg^iv	0.98	2.89	3.6754 (15)	138

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+3/2, y+1/2, z; (iii) x+3/2, −y−1/2, −z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NO₂
M_r	265.30
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	9.5730 (2), 8.7748 (2), 32.0620 (7)
V (Å³)	2693.25 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.30 × 0.30 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.651, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6569, 2764, 2410
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.101, 1.02
No. of reflections	2764
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8b···O1ⁱ	0.99	2.44	3.3102 (16)	147
C15—H15···N1ⁱⁱ	0.95	2.62	3.4250 (17)	143
C4—H4···Cgⁱⁱⁱ	0.95	2.82	3.5787 (14)	138
C17—H17c···Cg^iv	0.98	2.89	3.6754 (15)	138

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+3/2, y+1/2, z; (iii) x+3/2, −y−1/2, −z+1; (iv) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.

Acknowledgements

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (UM.C/HIR/MOHE/SC/12).

References

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