(E)-2-Cyano-3-[4-(dimethyl­amino)phen­yl]-N-phenyl­prop-2-enamide

Asiri, A.M.; Akkurt, M.; Khan, S.A.; Khan, I.U.; Arshad, M.N.

doi:10.1107/S1600536809017681

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1303

doi:10.1107/S1600536809017681

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(E)-2-Cyano-3-[4-(dimethylamino)phenyl]-N-phenylprop-2-enamide

Abdullah Mohamed Asiri,^a Mehmet Akkurt,^b ^* Salman A. Khan,^a Islam Ullah Khan ^c and Muhammad Nadeem Arshad ^c

^aChemistry Department, Faculty of Science, King Abdul-Aziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 11 May 2009; accepted 11 May 2009; online 14 May 2009)

In the title compound, C₁₈H₁₇N₃O, the dihedral angle between the phenyl and benzene rings is 11.22 (14)°. Apart from the methyl H atoms, the molecule is close to planar, with a maximum deviation of 0.145 (3) Å. Intramolecular C—H⋯O and C—H⋯N interactions occur. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur, resulting in an R₂²(12) ring motif. Further C—H⋯N and C—H⋯O bonds generate R₁²(7) and R₂²(22) motifs and a C—H⋯π interaction also occurs.

Related literature

For background on the properties and uses of organic dyes, see: Grabowski et al. (2003 ); Guo et al. (2007 ); Kwak et al. (2008 ); Moylan et al. (1996 ). For reference structural data, see Allen et al. (1987 ). For graph-set terminology, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₇N₃O
M_r = 291.35
Monoclinic, P 2₁ /c
a = 12.0639 (19) Å
b = 19.983 (3) Å
c = 6.3960 (9) Å
β = 94.870 (6)°
V = 1536.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.44 × 0.09 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
15701 measured reflections
3484 independent reflections
1380 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.165
S = 0.97
3484 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1	0.93	2.30	2.892 (4)	121
C12—H12⋯N2	0.93	2.61	3.445 (4)	149
N1—H1A⋯N2ⁱ	0.86	2.50	3.245 (3)	146
C1—H1⋯N2ⁱ	0.93	2.58	3.338 (4)	139
C18—H18A⋯O1ⁱⁱ	0.96	2.49	3.439 (4)	169
C3—H3⋯Cg1ⁱⁱⁱ	0.93	2.66	3.514 (3)	152
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 phenyl ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017681/hb2974sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017681/hb2974Isup2.hkl

checkCIF report

Comment top

Organic dyes with donor–π-conjugation–acceptor (D–π–A) molecular structure have attracted much attention because of their inherent nonlinear optical characteristics, which are highly sensitive to changes in the external environment such as polarity and pH of media, due to their intrinsic character (e.g. Grabowski et al., 2003). They have been intensively developed for applications using as photo-(PL) and electroluminescent (EL) materials in the fields of dye laser (Moylan et al., 1996), fluorescent sonser and logic memory (Guo et al., 2007), and organic light-emitting device (OLED) (Kwak et al., 2008). The title compound, (I) (Fig. 1), is a representative of Push-Pull systems with dimethylamino group as a donor at one end of the conjugated system and cyano and carboonyl as acceptor at the other end.

The molecule of (I) contains a phenyl ring and a benzene ring which makes a dihedral angle of 11.22 (14)°. Except the methyl H atoms, the title molecule is almost planar, with a maximum deviation of 0.145 (3) Å for C12 and C13. The bond lengths and angles are in normal range (Allen et al., 1987). The molecules of the title compound form in which two N—H···N hydrogen bonds. The N—H···N, C—H···N and C—H···O interactions generates R₂²(12), R₁²(7) and R₂²(22) motifs (Fig. 2) (Bernstein et al. 1995). Fig. 3 shows the molecular packing for (I) viewed down the a axis showing the hydrogen bonding interactions (dashed lines). Molecules form a zigzag pattern along the b axis.

The crystal structure is stabilized by intermolecular N—H···N, C—H···O and C—H···N hydrogen bonding, and C—H···π interactions (Table 1).

Related literature top

For background on the properties and uses of organic dyes, see: Grabowski et al. (2003); Guo et al. (2007); Kwak et al. (2008); Moylan et al. (1996). For reference structural data, see Allen et al. (1987). For graph-set terminology, see: Bernstein et al. (1995). Cg1 is the centroid of the C1–C6 phenyl ring.

Experimental top

N-Phenyl-2-cyanoacetamide (1.60 g, 0.010 mol) and 4-N,N-dimethylaminobenzaldehyde (1.49 g, 0.010 mol) were dissolved in 50 ml of ethanol then heated to boiling before pipyridine (0.5 ml) was added. The reaction mixture was refluxed for 7 h, cooled then the precipitate was filtered and recrystalized from ethanol to yield red prisms of (I) [yield: 90%, m.p.: 382–384 K]. IR;ν (cm ^-1): 3348, 2941, 2890 (–C—H), 2198 (CN), 1671 (C=O), 1601 (C=C), 1580 (C=C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. View of the hydrogen bonding interactions (dashed lines) for (I). H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (a) 1–x, –y, 1–z; (b) 1–x, –y, –z].
	Fig. 3. The molecular packing for (I) viewed down the a axis showing the hydrogen bonding interactions (dashed lines). Molecules form a zigzag pattern along the b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

(E)-2-Cyano-3-[4-(dimethylamino)phenyl]-N-phenylprop-2-enamide top

Crystal data top

C₁₈H₁₇N₃O	F(000) = 616
M_r = 291.35	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1223 reflections
a = 12.0639 (19) Å	θ = 3.4–19.8°
b = 19.983 (3) Å	µ = 0.08 mm⁻¹
c = 6.3960 (9) Å	T = 296 K
β = 94.870 (6)°	Prism, red
V = 1536.3 (4) Å³	0.44 × 0.09 × 0.07 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	1380 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.082
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ϕ and ω scans	h = −15→15
15701 measured reflections	k = −25→25
3484 independent reflections	l = −8→5

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.0643P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3484 reflections	Δρ_max = 0.19 e Å⁻³
202 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=KFc[1+0.001XFc²Λ³/sin(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (12)

Crystal data top

C₁₈H₁₇N₃O	V = 1536.3 (4) Å³
M_r = 291.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0639 (19) Å	µ = 0.08 mm⁻¹
b = 19.983 (3) Å	T = 296 K
c = 6.3960 (9) Å	0.44 × 0.09 × 0.07 mm
β = 94.870 (6)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1380 reflections with I > 2σ(I)
15701 measured reflections	R_int = 0.082
3484 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 0.97	Δρ_max = 0.19 e Å⁻³
3484 reflections	Δρ_min = −0.16 e Å⁻³
202 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.37797 (16)	0.07494 (10)	0.5929 (3)	0.0639 (8)
N1	0.19658 (18)	0.07922 (10)	0.6643 (3)	0.0444 (8)
N2	0.0364 (2)	−0.00214 (14)	0.2850 (4)	0.0714 (10)
N3	0.3109 (2)	−0.16820 (12)	−0.4827 (4)	0.0619 (10)
C1	0.1026 (3)	0.13303 (16)	0.9294 (5)	0.0740 (12)
C2	0.0994 (3)	0.17166 (17)	1.1086 (6)	0.0876 (17)
C3	0.1948 (4)	0.19793 (16)	1.2024 (5)	0.0757 (16)
C4	0.2923 (3)	0.18648 (16)	1.1198 (5)	0.0754 (14)
C5	0.2976 (3)	0.14743 (15)	0.9411 (5)	0.0615 (11)
C6	0.2018 (2)	0.12058 (13)	0.8457 (4)	0.0439 (10)
C7	0.2811 (2)	0.05968 (13)	0.5505 (4)	0.0425 (10)
C8	0.2467 (2)	0.01696 (13)	0.3648 (4)	0.0391 (9)
C9	0.1308 (3)	0.00579 (14)	0.3162 (4)	0.0480 (10)
C10	0.3244 (2)	−0.00906 (13)	0.2492 (4)	0.0414 (9)
C11	0.3150 (2)	−0.04902 (13)	0.0609 (4)	0.0392 (9)
C12	0.2159 (2)	−0.06559 (14)	−0.0565 (4)	0.0480 (10)
C13	0.2145 (2)	−0.10416 (14)	−0.2344 (4)	0.0488 (10)
C14	0.3122 (2)	−0.12898 (14)	−0.3082 (4)	0.0458 (10)
C15	0.4128 (2)	−0.11114 (14)	−0.1943 (4)	0.0506 (11)
C16	0.4124 (2)	−0.07274 (13)	−0.0153 (4)	0.0471 (10)
C17	0.2077 (3)	−0.18754 (16)	−0.5982 (5)	0.0770 (16)
C18	0.4122 (3)	−0.19039 (16)	−0.5680 (5)	0.0755 (15)
H1	0.03700	0.11530	0.86510	0.0890*
H1A	0.13160	0.06470	0.62090	0.0530*
H2	0.03200	0.17960	1.16470	0.1050*
H3	0.19290	0.22370	1.32310	0.0910*
H4	0.35720	0.20510	1.18370	0.0900*
H5	0.36550	0.13960	0.88690	0.0740*
H10	0.39720	0.00050	0.30000	0.0500*
H12	0.14890	−0.05000	−0.01300	0.0580*
H13	0.14660	−0.11400	−0.30780	0.0590*
H15	0.48010	−0.12540	−0.24010	0.0610*
H16	0.48010	−0.06220	0.05780	0.0570*
H17A	0.15590	−0.20220	−0.50190	0.1150*
H17B	0.22150	−0.22340	−0.69260	0.1150*
H17C	0.17720	−0.14990	−0.67680	0.1150*
H18A	0.46280	−0.15340	−0.57210	0.1130*
H18B	0.39490	−0.20720	−0.70750	0.1130*
H18C	0.44600	−0.22520	−0.48100	0.1130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0432 (13)	0.0847 (17)	0.0632 (13)	−0.0141 (12)	0.0010 (10)	−0.0260 (12)
N1	0.0437 (14)	0.0484 (15)	0.0409 (12)	−0.0052 (12)	0.0033 (11)	−0.0120 (11)
N2	0.0486 (17)	0.106 (2)	0.0607 (16)	−0.0128 (16)	0.0113 (13)	−0.0316 (15)
N3	0.0715 (19)	0.0641 (18)	0.0502 (14)	−0.0024 (15)	0.0063 (14)	−0.0211 (13)
C1	0.075 (2)	0.073 (2)	0.079 (2)	−0.031 (2)	0.035 (2)	−0.031 (2)
C2	0.108 (3)	0.075 (3)	0.088 (3)	−0.035 (2)	0.056 (2)	−0.036 (2)
C3	0.129 (4)	0.050 (2)	0.0486 (19)	−0.003 (2)	0.010 (2)	−0.0106 (16)
C4	0.087 (3)	0.068 (2)	0.066 (2)	0.019 (2)	−0.024 (2)	−0.0251 (19)
C5	0.061 (2)	0.059 (2)	0.0608 (19)	0.0158 (17)	−0.0159 (16)	−0.0210 (17)
C6	0.060 (2)	0.0341 (16)	0.0377 (14)	0.0019 (15)	0.0046 (15)	0.0007 (13)
C7	0.0429 (18)	0.0431 (18)	0.0412 (15)	−0.0066 (15)	0.0020 (14)	−0.0047 (13)
C8	0.0359 (16)	0.0451 (18)	0.0361 (13)	−0.0036 (13)	0.0013 (12)	0.0012 (12)
C9	0.0472 (19)	0.058 (2)	0.0396 (15)	−0.0055 (16)	0.0085 (14)	−0.0122 (14)
C10	0.0401 (16)	0.0427 (17)	0.0408 (14)	−0.0019 (14)	−0.0004 (13)	0.0003 (13)
C11	0.0377 (17)	0.0409 (17)	0.0387 (14)	−0.0017 (13)	0.0018 (13)	−0.0005 (13)
C12	0.0423 (18)	0.060 (2)	0.0425 (15)	0.0023 (15)	0.0080 (13)	−0.0058 (14)
C13	0.0477 (19)	0.058 (2)	0.0399 (15)	−0.0051 (15)	−0.0006 (13)	−0.0048 (14)
C14	0.058 (2)	0.0411 (18)	0.0389 (15)	−0.0003 (15)	0.0071 (15)	−0.0008 (13)
C15	0.051 (2)	0.049 (2)	0.0526 (17)	0.0034 (15)	0.0100 (15)	−0.0066 (15)
C16	0.0447 (18)	0.0462 (19)	0.0503 (16)	0.0012 (15)	0.0037 (14)	−0.0038 (14)
C17	0.093 (3)	0.079 (3)	0.057 (2)	−0.007 (2)	−0.0048 (19)	−0.0198 (18)
C18	0.098 (3)	0.073 (3)	0.0592 (19)	0.001 (2)	0.0285 (19)	−0.0163 (17)

Geometric parameters (Å, º) top

O1—C7	1.216 (3)	C12—C13	1.373 (4)
N1—C6	1.422 (3)	C13—C14	1.397 (4)
N1—C7	1.359 (3)	C14—C15	1.407 (4)
N2—C9	1.150 (4)	C15—C16	1.379 (4)
N3—C14	1.363 (4)	C1—H1	0.9300
N3—C17	1.445 (4)	C2—H2	0.9300
N3—C18	1.450 (4)	C3—H3	0.9300
N1—H1A	0.8600	C4—H4	0.9300
C1—C2	1.385 (5)	C5—H5	0.9300
C1—C6	1.375 (4)	C10—H10	0.9300
C2—C3	1.358 (6)	C12—H12	0.9300
C3—C4	1.349 (6)	C13—H13	0.9300
C4—C5	1.390 (4)	C15—H15	0.9300
C5—C6	1.370 (4)	C16—H16	0.9300
C7—C8	1.493 (4)	C17—H17A	0.9600
C8—C9	1.424 (4)	C17—H17B	0.9600
C8—C10	1.347 (4)	C17—H17C	0.9600
C10—C11	1.442 (4)	C18—H18A	0.9600
C11—C16	1.393 (3)	C18—H18B	0.9600
C11—C12	1.397 (4)	C18—H18C	0.9600

C6—N1—C7	128.4 (2)	C2—C1—H1	120.00
C14—N3—C17	121.5 (2)	C6—C1—H1	120.00
C14—N3—C18	122.2 (2)	C1—C2—H2	120.00
C17—N3—C18	116.3 (3)	C3—C2—H2	120.00
C6—N1—H1A	116.00	C2—C3—H3	120.00
C7—N1—H1A	116.00	C4—C3—H3	120.00
C2—C1—C6	120.6 (3)	C3—C4—H4	119.00
C1—C2—C3	119.9 (3)	C5—C4—H4	119.00
C2—C3—C4	119.7 (3)	C4—C5—H5	120.00
C3—C4—C5	121.3 (3)	C6—C5—H5	120.00
C4—C5—C6	119.4 (3)	C8—C10—H10	114.00
N1—C6—C5	124.7 (2)	C11—C10—H10	114.00
C1—C6—C5	119.0 (3)	C11—C12—H12	119.00
N1—C6—C1	116.3 (2)	C13—C12—H12	119.00
N1—C7—C8	114.8 (2)	C12—C13—H13	119.00
O1—C7—N1	124.0 (2)	C14—C13—H13	119.00
O1—C7—C8	121.2 (2)	C14—C15—H15	120.00
C9—C8—C10	122.4 (2)	C16—C15—H15	120.00
C7—C8—C10	119.9 (2)	C11—C16—H16	119.00
C7—C8—C9	117.7 (2)	C15—C16—H16	119.00
N2—C9—C8	177.1 (3)	N3—C17—H17A	109.00
C8—C10—C11	131.6 (2)	N3—C17—H17B	109.00
C12—C11—C16	116.1 (2)	N3—C17—H17C	109.00
C10—C11—C12	125.7 (2)	H17A—C17—H17B	109.00
C10—C11—C16	118.2 (2)	H17A—C17—H17C	109.00
C11—C12—C13	121.9 (2)	H17B—C17—H17C	110.00
C12—C13—C14	121.9 (2)	N3—C18—H18A	109.00
N3—C14—C15	121.3 (2)	N3—C18—H18B	109.00
N3—C14—C13	122.0 (2)	N3—C18—H18C	109.00
C13—C14—C15	116.8 (2)	H18A—C18—H18B	109.00
C14—C15—C16	120.5 (2)	H18A—C18—H18C	110.00
C11—C16—C15	122.9 (2)	H18B—C18—H18C	109.00

C6—N1—C7—O1	1.3 (4)	O1—C7—C8—C9	−175.1 (2)
C7—N1—C6—C1	179.4 (3)	O1—C7—C8—C10	4.5 (4)
C7—N1—C6—C5	−1.4 (4)	N1—C7—C8—C9	5.0 (3)
C6—N1—C7—C8	−178.8 (2)	C9—C8—C10—C11	2.3 (5)
C18—N3—C14—C15	−3.8 (4)	C7—C8—C10—C11	−177.2 (3)
C17—N3—C14—C13	−1.5 (4)	C8—C10—C11—C12	5.6 (5)
C18—N3—C14—C13	175.8 (3)	C8—C10—C11—C16	−175.5 (3)
C17—N3—C14—C15	179.0 (3)	C10—C11—C12—C13	−179.9 (3)
C2—C1—C6—N1	178.7 (3)	C16—C11—C12—C13	1.3 (4)
C2—C1—C6—C5	−0.6 (5)	C10—C11—C16—C15	−179.8 (2)
C6—C1—C2—C3	0.4 (5)	C12—C11—C16—C15	−0.8 (4)
C1—C2—C3—C4	0.3 (5)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—C5	−0.8 (5)	C12—C13—C14—N3	178.9 (3)
C3—C4—C5—C6	0.7 (5)	C12—C13—C14—C15	−1.6 (4)
C4—C5—C6—N1	−179.1 (3)	N3—C14—C15—C16	−178.5 (3)
C4—C5—C6—C1	0.0 (4)	C13—C14—C15—C16	2.0 (4)
N1—C7—C8—C10	−175.5 (2)	C14—C15—C16—C11	−0.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.30	2.892 (4)	121
C12—H12···N2	0.93	2.61	3.445 (4)	149
N1—H1A···N2ⁱ	0.86	2.50	3.245 (3)	146
C1—H1···N2ⁱ	0.93	2.58	3.338 (4)	139
C18—H18A···O1ⁱⁱ	0.96	2.49	3.439 (4)	169
C3—H3···Cg1ⁱⁱⁱ	0.93	2.66	3.514 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O
M_r	291.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0639 (19), 19.983 (3), 6.3960 (9)
β (°)	94.870 (6)
V (Å³)	1536.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.44 × 0.09 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15701, 3484, 1380
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.165, 0.97
No. of reflections	3484
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1	0.93	2.30	2.892 (4)	121
C12—H12···N2	0.93	2.61	3.445 (4)	149
N1—H1A···N2ⁱ	0.86	2.50	3.245 (3)	146
C1—H1···N2ⁱ	0.93	2.58	3.338 (4)	139
C18—H18A···O1ⁱⁱ	0.96	2.49	3.439 (4)	169
C3—H3···Cg1ⁱⁱⁱ	0.93	2.66	3.514 (3)	152

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

Acknowledgements

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing the laboratories and facilities.

References

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