3,3-Dimethyl-9-phenyl-3,4-dihydro­acridin-1(2H)-one

Ghorbani, HB.; Bazgir, A.

doi:10.1107/S1600536808022083

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1554

doi:10.1107/S1600536808022083

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3,3-Dimethyl-9-phenyl-3,4-dihydroacridin-1(2H)-one

Hosein Ghorbani ^a and Ayoob Bazgir ^a ^*

^aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran
^*Correspondence e-mail: a_bazgir@yahoo.com

(Received 11 July 2008; accepted 15 July 2008; online 19 July 2008)

In the molecule of the title compound, C₂₁H₁₉NO, the terminal saturated six-membered ring of the dihydroacridine unit adopts an envelope conformation, while the other two fused rings are nearly coplanar, with a dihedral angle of 2.61 (3)°. The coplanar ring system is oriented with respect to the phenyl ring at a dihedral angle of 74.58 (3)°. In the crystal structure, there is a C—H⋯π contact between the central ring of the dihydroacridine system and the phenyl ring and a π–π contact between the two central rings [centroid–centroid distance = 3.809 (1) Å].

Related literature

For general background, see: Kalluraya & Sreenivasa (1998 ); Doube et al. (1998 ); Maguire et al. (1994 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₁₉NO
M_r = 301.37
Monoclinic, C 2/c
a = 16.341 (3) Å
b = 11.3889 (18) Å
c = 18.772 (4) Å
β = 110.386 (14)°
V = 3274.8 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.33 × 0.22 × 0.1 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.980, T_max = 0.990
11268 measured reflections
3882 independent reflections
3032 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.143
S = 1.10
3882 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C8/C15/C20/C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1ⁱ	0.93	3.20	3.814 (3)	126
Symmetry code: (i) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022083/hk2495sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022083/hk2495Isup2.hkl

checkCIF report

Comment top

Recently, quinolines and their derivatives have received considerable attention, due to their wide range of therapeutic and biological properties. They have emerged as antimalarial, antiasthmatic, anti-inflamatory, antibacterial, anti- hypertensive and tyrosine kinase PDGF-RTK inhibiting agents. Moreover, poly- quinolines are found to undergo hierarchical self-assembly into a variety of nano and meso structures with enhanced electronic and photonic functions (Kalluraya & Sreenivasa, 1998; Doube et al., 1998; Maguire et al., 1994). We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1/C2/C5-C7/C21) adopts envelope conformation, with C2 atom displaced by -0.683 (3) Å from the plane of the other ring atoms. Rings B (N1/C7/C8/C15/C20/C21), C (C15-C20) and D (C9-C14) are, of course, planar and they are oriented at dihedral angles of B/C = 2.61 (3)°, B/D = 74.17 (3)° and C/D = 75.01 (3)°. So, rings B and C are nearly coplanar. The coplanar ring system is oriented with respect to the phenyl ring D at a dihedral angle of 74.58 (3)°.

In the crystal structure, a C—H···π contact (Table 1) between rings B and D and a π—π contact between the symmetry related B rings Cg1···Cg1ⁱ [symmetry code: (i) 1/2 - x, 3/2 - y, - z, where Cg1 is the centroid of ring B] may stabilize the structure, with centroid-centroid distance of 3.809 (1) Å.

Related literature top

For general background, see: Kalluraya & Sreenivasa (1998); Doube et al. (1998); Maguire et al. (1994). For bond-length data, see: Allen et al. (1987). Cg1 is the centroid of the N1/C7/C8/C15/C20/C21 ring.

Experimental top

For the preparation of the title compound, a mixture of 5,5-dimethylcyclohexane -1,3-dione (1 mmol), (2-aminophenyl)(phenyl)methanone (1 mmol) and benzyl tri- ethyl ammonium chloride (0.1 g) in water (5 ml) was stirred at reflux for 5 h. After completion of reaction (monitored by TLC) the reaction mixture was filtered and the precipitate washed with water (15 ml), and then recrystallized from EtOH/water (1:2) to afford the pure product (yield; 0.195 g, 65%).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

3,3-Dimethyl-9-phenyl-3,4-dihydroacridin-1(2H)-one top

Crystal data top

C₂₁H₁₉NO	F(000) = 1280
M_r = 301.37	D_x = 1.222 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1575 reflections
a = 16.341 (3) Å	θ = 2.2–28.0°
b = 11.3889 (18) Å	µ = 0.08 mm⁻¹
c = 18.772 (4) Å	T = 298 K
β = 110.386 (14)°	Block, colorless
V = 3274.8 (10) Å³	0.33 × 0.22 × 0.1 mm
Z = 8

Data collection top

Stoe IPDSII diffractometer	3032 reflections with I > 2σ(I)
rotation method scans	R_int = 0.044
Absorption correction: numerical shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)	θ_max = 28.0°, θ_min = 2.2°
T_min = 0.980, T_max = 0.990	h = −21→21
11268 measured reflections	k = −14→15
3882 independent reflections	l = −24→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.0491P)² + 1.8747P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.143	(Δ/σ)_max = 0.002
S = 1.10	Δρ_max = 0.24 e Å⁻³
3882 reflections	Δρ_min = −0.26 e Å⁻³
208 parameters

Crystal data top

C₂₁H₁₉NO	V = 3274.8 (10) Å³
M_r = 301.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.341 (3) Å	µ = 0.08 mm⁻¹
b = 11.3889 (18) Å	T = 298 K
c = 18.772 (4) Å	0.33 × 0.22 × 0.1 mm
β = 110.386 (14)°

Data collection top

Stoe IPDSII diffractometer	3882 independent reflections
Absorption correction: numerical shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)	3032 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.044
11268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.10	Δρ_max = 0.24 e Å⁻³
3882 reflections	Δρ_min = −0.26 e Å⁻³
208 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.81274 (12)	0.40574 (13)	−0.19111 (8)	0.0814 (5)
N1	0.88041 (9)	0.16743 (13)	0.03136 (8)	0.0490 (3)
C1	0.87761 (13)	0.08450 (15)	−0.08673 (11)	0.0533 (4)
H1A	0.8206	0.048	−0.1079	0.064*
H1B	0.9169	0.0277	−0.0535	0.064*
C2	0.91044 (11)	0.11403 (15)	−0.15138 (10)	0.0494 (4)
C3	0.90577 (17)	0.00459 (19)	−0.20010 (14)	0.0736 (6)
H3A	0.9239	0.0244	−0.2421	0.088*
H3B	0.8469	−0.0242	−0.219	0.088*
H3C	0.9436	−0.055	−0.1698	0.088*
C4	1.00438 (13)	0.1581 (2)	−0.12016 (13)	0.0681 (6)
H4A	1.0074	0.2267	−0.0897	0.082*
H4B	1.0236	0.1773	−0.1616	0.082*
H4C	1.0413	0.0979	−0.0896	0.082*
C5	0.85007 (13)	0.20855 (17)	−0.19917 (10)	0.0570 (4)
H5A	0.8728	0.234	−0.238	0.068*
H5B	0.7933	0.1736	−0.2249	0.068*
C6	0.83780 (12)	0.31480 (15)	−0.15688 (9)	0.0493 (4)
C7	0.85331 (10)	0.30320 (13)	−0.07363 (9)	0.0405 (3)
C8	0.84960 (9)	0.39807 (14)	−0.02880 (9)	0.0411 (3)
C9	0.83425 (10)	0.52170 (14)	−0.05688 (9)	0.0423 (3)
C10	0.90001 (12)	0.58667 (17)	−0.06880 (11)	0.0550 (4)
H10	0.9535	0.5517	−0.0623	0.066*
C11	0.88648 (13)	0.70308 (17)	−0.09023 (12)	0.0635 (5)
H11	0.9312	0.7465	−0.0973	0.076*
C12	0.80695 (14)	0.75516 (16)	−0.10110 (11)	0.0626 (5)
H12	0.7977	0.8333	−0.1162	0.075*
C13	0.74135 (13)	0.69126 (16)	−0.08949 (12)	0.0595 (5)
H13	0.6877	0.7264	−0.0968	0.071*
C14	0.75471 (11)	0.57519 (15)	−0.06710 (10)	0.0496 (4)
H14	0.7102	0.5327	−0.0589	0.06*
C15	0.86231 (10)	0.37692 (15)	0.04941 (9)	0.0436 (4)
C16	0.86349 (12)	0.46714 (19)	0.10169 (11)	0.0584 (5)
H16	0.8566	0.5449	0.0856	0.07*
C17	0.87457 (14)	0.4412 (2)	0.17538 (11)	0.0720 (6)
H17	0.8753	0.5013	0.2091	0.086*
C18	0.88480 (14)	0.3247 (2)	0.20068 (11)	0.0746 (6)
H18	0.8914	0.308	0.2509	0.09*
C19	0.88514 (13)	0.2360 (2)	0.15250 (11)	0.0640 (5)
H19	0.8919	0.159	0.17	0.077*
C20	0.87526 (10)	0.25947 (16)	0.07591 (9)	0.0464 (4)
C21	0.87064 (10)	0.18891 (14)	−0.04023 (9)	0.0429 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1371 (15)	0.0625 (8)	0.0472 (7)	0.0205 (9)	0.0353 (8)	0.0142 (7)
N1	0.0525 (8)	0.0514 (8)	0.0475 (8)	0.0020 (6)	0.0228 (6)	0.0132 (6)
C1	0.0635 (11)	0.0421 (8)	0.0588 (10)	−0.0016 (8)	0.0269 (9)	0.0013 (8)
C2	0.0542 (9)	0.0484 (9)	0.0504 (9)	−0.0015 (8)	0.0241 (8)	−0.0063 (7)
C3	0.0902 (15)	0.0633 (12)	0.0775 (14)	−0.0042 (11)	0.0420 (12)	−0.0184 (11)
C4	0.0554 (11)	0.0764 (13)	0.0784 (14)	−0.0041 (10)	0.0310 (10)	−0.0112 (11)
C5	0.0679 (11)	0.0613 (11)	0.0427 (9)	−0.0011 (9)	0.0205 (8)	−0.0042 (8)
C6	0.0590 (10)	0.0507 (9)	0.0398 (8)	0.0030 (8)	0.0192 (7)	0.0076 (7)
C7	0.0420 (8)	0.0436 (8)	0.0388 (8)	0.0000 (6)	0.0177 (6)	0.0050 (6)
C8	0.0386 (7)	0.0455 (8)	0.0421 (8)	0.0000 (6)	0.0178 (6)	0.0053 (7)
C9	0.0469 (8)	0.0433 (8)	0.0384 (8)	−0.0016 (7)	0.0170 (6)	0.0009 (6)
C10	0.0464 (9)	0.0595 (11)	0.0592 (11)	−0.0024 (8)	0.0187 (8)	0.0118 (9)
C11	0.0650 (12)	0.0596 (11)	0.0626 (12)	−0.0196 (9)	0.0179 (9)	0.0093 (9)
C12	0.0777 (13)	0.0381 (9)	0.0645 (12)	−0.0062 (9)	0.0152 (10)	0.0042 (8)
C13	0.0607 (11)	0.0460 (9)	0.0703 (12)	0.0065 (8)	0.0211 (9)	0.0007 (9)
C14	0.0509 (9)	0.0445 (9)	0.0579 (10)	−0.0011 (7)	0.0245 (8)	0.0008 (8)
C15	0.0397 (8)	0.0541 (9)	0.0403 (8)	0.0025 (7)	0.0181 (6)	0.0028 (7)
C16	0.0604 (11)	0.0676 (12)	0.0499 (10)	0.0043 (9)	0.0225 (8)	−0.0059 (9)
C17	0.0737 (13)	0.0998 (17)	0.0458 (10)	0.0081 (12)	0.0249 (9)	−0.0129 (11)
C18	0.0731 (13)	0.1169 (19)	0.0388 (9)	0.0139 (13)	0.0258 (9)	0.0106 (11)
C19	0.0648 (11)	0.0863 (14)	0.0458 (10)	0.0096 (10)	0.0253 (8)	0.0206 (10)
C20	0.0419 (8)	0.0604 (10)	0.0409 (8)	0.0014 (7)	0.0195 (6)	0.0103 (7)
C21	0.0426 (8)	0.0447 (8)	0.0450 (8)	−0.0009 (6)	0.0198 (7)	0.0064 (7)

Geometric parameters (Å, º) top

C1—C21	1.503 (2)	C9—C14	1.387 (2)
C1—C2	1.526 (2)	C10—C11	1.381 (3)
C1—H1A	0.97	C10—H10	0.93
C1—H1B	0.97	C11—C12	1.377 (3)
C2—C5	1.523 (3)	C11—H11	0.93
C2—C4	1.525 (3)	C12—C13	1.375 (3)
C2—C3	1.532 (3)	C12—H12	0.93
C3—H3A	0.96	C13—C14	1.381 (2)
C3—H3B	0.96	C13—H13	0.93
C3—H3C	0.96	C14—H14	0.93
C4—H4A	0.96	C15—C16	1.416 (2)
C4—H4B	0.96	C15—C20	1.417 (2)
C4—H4C	0.96	C16—C17	1.364 (3)
C5—C6	1.499 (2)	C16—H16	0.93
C5—H5A	0.97	C17—C18	1.399 (3)
C5—H5B	0.97	C17—H17	0.93
C6—O1	1.212 (2)	C18—C19	1.357 (3)
C6—C7	1.499 (2)	C18—H18	0.93
C7—C8	1.384 (2)	C19—C20	1.415 (2)
C7—C21	1.430 (2)	C19—H19	0.93
C8—C15	1.430 (2)	C20—N1	1.362 (2)
C8—C9	1.494 (2)	C21—N1	1.320 (2)
C9—C10	1.386 (2)

C21—C1—C2	113.98 (14)	C10—C9—C8	121.06 (15)
C21—C1—H1A	108.8	C14—C9—C8	119.80 (14)
C2—C1—H1A	108.8	C11—C10—C9	120.35 (18)
C21—C1—H1B	108.8	C11—C10—H10	119.8
C2—C1—H1B	108.8	C9—C10—H10	119.8
H1A—C1—H1B	107.7	C12—C11—C10	120.24 (17)
C5—C2—C4	110.65 (16)	C12—C11—H11	119.9
C5—C2—C1	106.81 (14)	C10—C11—H11	119.9
C4—C2—C1	110.65 (16)	C13—C12—C11	119.75 (17)
C5—C2—C3	109.63 (16)	C13—C12—H12	120.1
C4—C2—C3	109.35 (16)	C11—C12—H12	120.1
C1—C2—C3	109.72 (15)	C12—C13—C14	120.38 (18)
C2—C3—H3A	109.5	C12—C13—H13	119.8
C2—C3—H3B	109.5	C14—C13—H13	119.8
H3A—C3—H3B	109.5	C13—C14—C9	120.24 (16)
C2—C3—H3C	109.5	C13—C14—H14	119.9
H3A—C3—H3C	109.5	C9—C14—H14	119.9
H3B—C3—H3C	109.5	C16—C15—C20	118.51 (16)
C2—C4—H4A	109.5	C16—C15—C8	123.45 (16)
C2—C4—H4B	109.5	C20—C15—C8	118.04 (15)
H4A—C4—H4B	109.5	C17—C16—C15	120.7 (2)
C2—C4—H4C	109.5	C17—C16—H16	119.7
H4A—C4—H4C	109.5	C15—C16—H16	119.7
H4B—C4—H4C	109.5	C16—C17—C18	120.5 (2)
C6—C5—C2	115.93 (15)	C16—C17—H17	119.7
C6—C5—H5A	108.3	C18—C17—H17	119.7
C2—C5—H5A	108.3	C19—C18—C17	120.46 (19)
C6—C5—H5B	108.3	C19—C18—H18	119.8
C2—C5—H5B	108.3	C17—C18—H18	119.8
H5A—C5—H5B	107.4	C18—C19—C20	120.8 (2)
O1—C6—C5	119.46 (16)	C18—C19—H19	119.6
O1—C6—C7	122.07 (16)	C20—C19—H19	119.6
C5—C6—C7	118.41 (15)	N1—C20—C19	117.99 (17)
C8—C7—C21	119.22 (14)	N1—C20—C15	123.00 (14)
C8—C7—C6	122.53 (14)	C19—C20—C15	119.00 (17)
C21—C7—C6	118.23 (14)	N1—C21—C7	123.40 (15)
C7—C8—C15	118.13 (14)	N1—C21—C1	115.98 (14)
C7—C8—C9	123.98 (14)	C7—C21—C1	120.62 (14)
C15—C8—C9	117.88 (14)	C21—N1—C20	118.11 (14)
C10—C9—C14	119.03 (15)

C21—C1—C2—C5	−55.2 (2)	C8—C9—C14—C13	176.85 (16)
C21—C1—C2—C4	65.3 (2)	C7—C8—C15—C16	177.41 (15)
C21—C1—C2—C3	−173.95 (17)	C9—C8—C15—C16	−1.8 (2)
C4—C2—C5—C6	−67.6 (2)	C7—C8—C15—C20	−1.9 (2)
C1—C2—C5—C6	52.9 (2)	C9—C8—C15—C20	178.84 (14)
C3—C2—C5—C6	171.73 (16)	C20—C15—C16—C17	−1.7 (3)
C2—C5—C6—O1	158.93 (18)	C8—C15—C16—C17	178.98 (17)
C2—C5—C6—C7	−23.8 (2)	C15—C16—C17—C18	−0.1 (3)
O1—C6—C7—C8	−7.4 (3)	C16—C17—C18—C19	1.0 (3)
C5—C6—C7—C8	175.35 (16)	C17—C18—C19—C20	0.1 (3)
O1—C6—C7—C21	171.17 (18)	C18—C19—C20—N1	176.85 (18)
C5—C6—C7—C21	−6.1 (2)	C18—C19—C20—C15	−1.9 (3)
C21—C7—C8—C15	−0.8 (2)	C16—C15—C20—N1	−176.02 (16)
C6—C7—C8—C15	177.79 (14)	C8—C15—C20—N1	3.4 (2)
C21—C7—C8—C9	178.40 (14)	C16—C15—C20—C19	2.7 (2)
C6—C7—C8—C9	−3.0 (2)	C8—C15—C20—C19	−177.96 (15)
C7—C8—C9—C10	−76.1 (2)	C8—C7—C21—N1	2.5 (2)
C15—C8—C9—C10	103.06 (18)	C6—C7—C21—N1	−176.10 (15)
C7—C8—C9—C14	107.68 (19)	C8—C7—C21—C1	−178.28 (15)
C15—C8—C9—C14	−73.2 (2)	C6—C7—C21—C1	3.1 (2)
C14—C9—C10—C11	0.3 (3)	C2—C1—C21—N1	−151.45 (15)
C8—C9—C10—C11	−175.97 (17)	C2—C1—C21—C7	29.3 (2)
C9—C10—C11—C12	−1.0 (3)	C7—C21—N1—C20	−1.2 (2)
C10—C11—C12—C13	0.9 (3)	C1—C21—N1—C20	179.53 (15)
C11—C12—C13—C14	−0.1 (3)	C19—C20—N1—C21	179.55 (15)
C12—C13—C14—C9	−0.7 (3)	C15—C20—N1—C21	−1.8 (2)
C10—C9—C14—C13	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	3.20	3.814 (3)	126

Symmetry code: (i) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉NO
M_r	301.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	16.341 (3), 11.3889 (18), 18.772 (4)
β (°)	110.386 (14)
V (Å³)	3274.8 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.33 × 0.22 × 0.1

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	11268, 3882, 3032
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.143, 1.10
No. of reflections	3882
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1ⁱ	0.93	3.197	3.814 (3)	125.65

Symmetry code: (i) x+1/2, y+3/2, z.

Acknowledgements

I am grateful to the Islamic Azad University, Dorood Branch, for financial support.

References

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