6,6′-Di­nitro-1,1′-(ethane-1,2-di­yl)di(1H-indazole)

Kouakou, A.; Rakib, E.M.; El Malki, A.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536814004516

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o390

doi:10.1107/S1600536814004516

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6,6′-Dinitro-1,1′-(ethane-1,2-diyl)di(1H-indazole)

Assoman Kouakou,^a ^* El Mostapha Rakib,^a Abdelghani El Malki,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: assoman_k@yahoo.fr

(Received 24 February 2014; accepted 26 February 2014; online 5 March 2014)

The molecule of the title compound, C₁₆H₁₂N₆O₄, is built up from two fused five- and six-membered rings linked by an ethylene group. The dihedral angle between the planes through the indazole ring systems is 39.74 (5)°. The nitro groups are tilted by 7.2 (2) and 8.5 (2)° with respect to planes of the fused-ring systems. In the crystal, molecules are linked by C—H⋯N and C—H⋯O hydrogen bonds into chains running parallel to the c axis.

CCDC reference: 988920

Related literature

For biological activities of the indazole moiety, see: Ali et al. (2012 ); Abbassi et al. (2012 ); Plescia et al. (2010 ); Lee et al. (2001 ); Liu et al. (2011 ). For related compounds, see: Kouakou et al. (2013 ); Chicha et al. (2013 ).

Experimental

Crystal data

C₁₆H₁₂N₆O₄
M_r = 352.32
Monoclinic, P 2₁ /c
a = 9.410 (5) Å
b = 12.064 (5) Å
c = 14.804 (4) Å
β = 109.01 (2)°
V = 1588.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.37 × 0.32 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer
16446 measured reflections
3503 independent reflections
2667 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.03
3503 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N5ⁱ	0.93	2.48	3.344 (2)	154
C15—H15⋯O1ⁱ	0.93	2.47	3.401 (2)	179
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 988920

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814004516/rz5107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004516/rz5107Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004516/rz5107Isup3.cml

checkCIF report

Comment top

Indazole moiety have been nucleus is a pharmaceutically important and emerging heterocycle with a broad spectrum of activities including anti-microbial1, anti-cancer, anti-inflammatory, anti- platelet, and selective 5-HT6 antagonists (Ali et al., 2012; Abbassi et al., 2012; Plescia et al., 2010; Lee et al., 2001; Liu et al., 2011). The present work is a continuation of the investigation on the indazole derivatives published recently by our team (Kouakou et al., 2013; Chicha et al., 2013).

The molecule of the title compound is formed by two fused five- and six-membered rings linked by an ethylene group and connected to two nitro groups as shown in Fig. 1. The two fused ring systems (N2/N3/C1–C7 and N4/N5C10–C16) make dihedral angles of 7.2 (2)° and 8.5 (2)° with the planes through the attached nitro groups (N1/O1/O2 and N6/O3(O4), respectively. The dihedral angle between the indazole ring systems is 39.74 (5)°. In the crystal, molecules are linked by C7—H7···N5 and C15—H15···O1 hydrogen interactions (Table 1) into chains running parallel to the [0 0 1] direction as shown in Fig. 2.

Related literature top

For biological activities of the indazole moiety, see: Ali et al. (2012); Abbassi et al. (2012); Plescia et al. (2010); Lee et al. (2001); Liu et al. (2011). For related compounds, see: Kouakou et al. (2013); Chicha et al. (2013).

Experimental top

A solution of 6-nitroindazole (0.5 g, 3.06 mmol) and KOH (0.17 g, 3.08 mmol) in EtOH (15 ml) was heated under reflux for 48 h. The mixture was cooled and the solvent removed from the filtrate in vacuo. The formed 6-nitroindazole potassium salt and 1,2-ethylene dibromide (0.27 ml, 1.48 mmol) was heated in dimethylformamide (5 ml) under reflux for 3 h. The mixture was then cooled, all volatiles were removed in vacuo and water was added. The precipitate was filtered and was purified by column chromatography (EtOAc/hexane 2:8 v/v). The title compound was recrystallized from acetone (yield: 35%; m. p.: 468 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Partial crystal packing of the title compound showing a chain of molecules linked by hydrogen bonds (dashed lines).

6,6'-Dinitro-1,1'-(ethane-1,2-diyl)di(1H-indazole) top

Crystal data top

C₁₆H₁₂N₆O₄	F(000) = 728
M_r = 352.32	D_x = 1.473 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3672 reflections
a = 9.410 (5) Å	θ = 1.5–27.1°
b = 12.064 (5) Å	µ = 0.11 mm⁻¹
c = 14.804 (4) Å	T = 296 K
β = 109.01 (2)°	Block, colourless
V = 1588.9 (12) Å³	0.37 × 0.32 × 0.26 mm
Z = 4

Data collection top

Bruker X8 APEX diffractometer	2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 27.1°, θ_min = 2.8°
ϕ and ω scans	h = −12→12
16446 measured reflections	k = −15→15
3503 independent reflections	l = −18→18

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0493P)² + 0.3594P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3503 reflections	Δρ_max = 0.20 e Å⁻³
236 parameters	Δρ_min = −0.19 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: 0.0033 (10)

Crystal data top

C₁₆H₁₂N₆O₄	V = 1588.9 (12) Å³
M_r = 352.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.410 (5) Å	µ = 0.11 mm⁻¹
b = 12.064 (5) Å	T = 296 K
c = 14.804 (4) Å	0.37 × 0.32 × 0.26 mm
β = 109.01 (2)°

Data collection top

Bruker X8 APEX diffractometer	2667 reflections with I > 2σ(I)
16446 measured reflections	R_int = 0.033
3503 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3503 reflections	Δρ_min = −0.19 e Å⁻³
236 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	0.72668 (16)	0.44512 (14)	0.20575 (10)	0.0753 (4)
O2	0.8642 (2)	0.57503 (14)	0.28985 (14)	0.1037 (6)
O3	1.06798 (18)	0.14604 (14)	0.75890 (9)	0.0817 (5)
O4	1.28535 (16)	0.17800 (15)	0.74730 (11)	0.0990 (6)
N1	0.78171 (17)	0.49484 (13)	0.28105 (13)	0.0617 (4)
N2	0.53003 (16)	0.25102 (14)	0.54188 (9)	0.0580 (4)
N3	0.54014 (13)	0.24766 (11)	0.45233 (8)	0.0435 (3)
N4	0.74940 (12)	0.09097 (10)	0.40649 (8)	0.0384 (3)
N5	0.74567 (15)	0.09998 (12)	0.31430 (8)	0.0487 (3)
N6	1.15060 (18)	0.16124 (12)	0.71175 (11)	0.0612 (4)
C1	0.74301 (17)	0.45822 (13)	0.36515 (12)	0.0474 (4)
C2	0.7928 (2)	0.52228 (15)	0.44873 (15)	0.0630 (5)
H2	0.8535	0.5839	0.4515	0.076*
C3	0.7517 (2)	0.49382 (17)	0.52569 (14)	0.0669 (5)
H3	0.7817	0.5367	0.5809	0.080*
C4	0.66362 (18)	0.39900 (15)	0.52037 (11)	0.0504 (4)
C5	0.62089 (15)	0.33505 (12)	0.43641 (10)	0.0386 (3)
C6	0.65760 (16)	0.36455 (12)	0.35590 (10)	0.0407 (3)
H6	0.6263	0.3234	0.2997	0.049*
C7	0.6008 (2)	0.34107 (18)	0.58152 (12)	0.0645 (5)
H7	0.6090	0.3644	0.6429	0.077*
C8	0.49431 (15)	0.14827 (13)	0.39587 (11)	0.0439 (4)
H8A	0.4747	0.1659	0.3290	0.053*
H8B	0.4017	0.1208	0.4030	0.053*
C9	0.61375 (15)	0.05839 (13)	0.42568 (11)	0.0443 (4)
H9A	0.6375	0.0436	0.4934	0.053*
H9B	0.5748	−0.0094	0.3912	0.053*
C10	0.87881 (19)	0.13663 (14)	0.31726 (11)	0.0505 (4)
H10	0.9067	0.1501	0.2635	0.061*
C11	0.97408 (16)	0.15298 (12)	0.41201 (10)	0.0401 (3)
C12	1.12332 (17)	0.18656 (13)	0.45625 (13)	0.0511 (4)
H12	1.1830	0.2074	0.4199	0.061*
C13	1.17921 (16)	0.18815 (13)	0.55331 (13)	0.0520 (4)
H13	1.2785	0.2087	0.5841	0.062*
C14	1.08659 (16)	0.15870 (12)	0.60685 (11)	0.0433 (4)
C15	0.93939 (15)	0.12611 (12)	0.56797 (10)	0.0375 (3)
H15	0.8802	0.1076	0.6052	0.045*
C16	0.88544 (14)	0.12277 (11)	0.46851 (9)	0.0337 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0816 (9)	0.0892 (11)	0.0650 (9)	0.0071 (8)	0.0377 (7)	0.0152 (8)
O2	0.1124 (13)	0.0726 (11)	0.1501 (16)	−0.0232 (10)	0.0756 (12)	0.0175 (10)
O3	0.0884 (10)	0.1023 (12)	0.0437 (7)	0.0028 (9)	0.0066 (7)	−0.0094 (7)
O4	0.0647 (9)	0.1077 (13)	0.0874 (11)	−0.0184 (8)	−0.0262 (8)	−0.0118 (9)
N1	0.0585 (9)	0.0505 (9)	0.0863 (12)	0.0087 (7)	0.0376 (8)	0.0203 (8)
N2	0.0521 (8)	0.0823 (11)	0.0423 (8)	0.0015 (8)	0.0193 (6)	0.0077 (7)
N3	0.0397 (6)	0.0518 (8)	0.0396 (7)	−0.0015 (6)	0.0139 (5)	0.0034 (5)
N4	0.0345 (6)	0.0445 (7)	0.0350 (6)	−0.0009 (5)	0.0096 (5)	0.0047 (5)
N5	0.0539 (8)	0.0556 (8)	0.0348 (7)	0.0022 (6)	0.0122 (5)	0.0045 (6)
N6	0.0602 (9)	0.0482 (9)	0.0565 (9)	−0.0003 (7)	−0.0065 (7)	−0.0092 (7)
C1	0.0448 (8)	0.0398 (9)	0.0594 (10)	0.0049 (7)	0.0195 (7)	0.0067 (7)
C2	0.0607 (11)	0.0428 (10)	0.0824 (13)	−0.0098 (8)	0.0189 (9)	−0.0067 (9)
C3	0.0704 (12)	0.0604 (12)	0.0614 (12)	−0.0067 (9)	0.0098 (9)	−0.0233 (9)
C4	0.0484 (8)	0.0589 (11)	0.0403 (8)	0.0030 (8)	0.0096 (7)	−0.0072 (7)
C5	0.0340 (7)	0.0411 (8)	0.0386 (7)	0.0026 (6)	0.0088 (6)	0.0006 (6)
C6	0.0425 (8)	0.0388 (8)	0.0402 (8)	0.0044 (6)	0.0126 (6)	0.0003 (6)
C7	0.0645 (11)	0.0929 (15)	0.0362 (9)	0.0050 (10)	0.0164 (8)	−0.0053 (9)
C8	0.0307 (7)	0.0476 (9)	0.0490 (8)	−0.0051 (6)	0.0068 (6)	0.0043 (7)
C9	0.0341 (7)	0.0446 (9)	0.0510 (9)	−0.0058 (6)	0.0095 (6)	0.0098 (7)
C10	0.0589 (10)	0.0556 (10)	0.0445 (9)	0.0084 (8)	0.0272 (7)	0.0085 (7)
C11	0.0410 (7)	0.0369 (8)	0.0481 (8)	0.0058 (6)	0.0221 (6)	0.0066 (6)
C12	0.0387 (8)	0.0456 (9)	0.0772 (12)	0.0017 (7)	0.0300 (8)	0.0100 (8)
C13	0.0307 (7)	0.0395 (9)	0.0805 (12)	−0.0024 (6)	0.0110 (7)	0.0025 (8)
C14	0.0396 (7)	0.0328 (8)	0.0494 (9)	0.0009 (6)	0.0035 (6)	−0.0035 (6)
C15	0.0376 (7)	0.0354 (7)	0.0399 (7)	0.0015 (6)	0.0132 (6)	0.0017 (6)
C16	0.0304 (6)	0.0311 (7)	0.0397 (7)	0.0020 (5)	0.0117 (5)	0.0027 (5)

Geometric parameters (Å, º) top

O1—N1	1.223 (2)	C4—C7	1.416 (3)
O2—N1	1.220 (2)	C5—C6	1.391 (2)
O3—N6	1.216 (2)	C6—H6	0.9300
O4—N6	1.221 (2)	C7—H7	0.9300
N1—C1	1.474 (2)	C8—C9	1.520 (2)
N2—C7	1.309 (3)	C8—H8A	0.9700
N2—N3	1.3603 (18)	C8—H8B	0.9700
N3—C5	1.3643 (19)	C9—H9A	0.9700
N3—C8	1.445 (2)	C9—H9B	0.9700
N4—N5	1.3581 (17)	C10—C11	1.411 (2)
N4—C16	1.3650 (18)	C10—H10	0.9300
N4—C9	1.4494 (19)	C11—C12	1.402 (2)
N5—C10	1.316 (2)	C11—C16	1.4082 (19)
N6—C14	1.472 (2)	C12—C13	1.360 (2)
C1—C6	1.367 (2)	C12—H12	0.9300
C1—C2	1.404 (2)	C13—C14	1.401 (2)
C2—C3	1.361 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.373 (2)
C3—C4	1.400 (3)	C15—C16	1.3929 (19)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.406 (2)

O2—N1—O1	123.51 (18)	C4—C7—H7	123.8
O2—N1—C1	118.09 (18)	N3—C8—C9	111.77 (12)
O1—N1—C1	118.37 (15)	N3—C8—H8A	109.3
C7—N2—N3	105.94 (14)	C9—C8—H8A	109.3
N2—N3—C5	111.41 (13)	N3—C8—H8B	109.3
N2—N3—C8	119.09 (13)	C9—C8—H8B	109.3
C5—N3—C8	128.28 (12)	H8A—C8—H8B	107.9
N5—N4—C16	111.41 (11)	N4—C9—C8	111.39 (12)
N5—N4—C9	118.85 (11)	N4—C9—H9A	109.3
C16—N4—C9	129.58 (12)	C8—C9—H9A	109.3
C10—N5—N4	106.31 (12)	N4—C9—H9B	109.3
O3—N6—O4	123.09 (18)	C8—C9—H9B	109.3
O3—N6—C14	118.95 (15)	H9A—C9—H9B	108.0
O4—N6—C14	117.96 (18)	N5—C10—C11	111.71 (13)
C6—C1—C2	124.04 (16)	N5—C10—H10	124.1
C6—C1—N1	117.51 (15)	C11—C10—H10	124.1
C2—C1—N1	118.44 (16)	C12—C11—C16	119.62 (14)
C3—C2—C1	119.66 (17)	C12—C11—C10	136.07 (14)
C3—C2—H2	120.2	C16—C11—C10	104.29 (13)
C1—C2—H2	120.2	C13—C12—C11	118.78 (14)
C2—C3—C4	118.92 (16)	C13—C12—H12	120.6
C2—C3—H3	120.5	C11—C12—H12	120.6
C4—C3—H3	120.5	C12—C13—C14	119.75 (14)
C3—C4—C5	119.45 (16)	C12—C13—H13	120.1
C3—C4—C7	136.90 (17)	C14—C13—H13	120.1
C5—C4—C7	103.63 (16)	C15—C14—C13	124.32 (15)
N3—C5—C6	130.81 (13)	C15—C14—N6	117.30 (15)
N3—C5—C4	106.64 (13)	C13—C14—N6	118.38 (14)
C6—C5—C4	122.54 (15)	C14—C15—C16	114.97 (13)
C1—C6—C5	115.31 (14)	C14—C15—H15	122.5
C1—C6—H6	122.3	C16—C15—H15	122.5
C5—C6—H6	122.3	N4—C16—C15	131.16 (12)
N2—C7—C4	112.36 (15)	N4—C16—C11	106.28 (12)
N2—C7—H7	123.8	C15—C16—C11	122.54 (13)

C7—N2—N3—C5	1.38 (17)	C5—N3—C8—C9	87.72 (18)
C7—N2—N3—C8	169.77 (14)	N5—N4—C9—C8	−68.45 (17)
C16—N4—N5—C10	0.40 (17)	C16—N4—C9—C8	106.61 (16)
C9—N4—N5—C10	176.31 (14)	N3—C8—C9—N4	−65.19 (17)
O2—N1—C1—C6	−176.34 (16)	N4—N5—C10—C11	−0.10 (18)
O1—N1—C1—C6	5.4 (2)	N5—C10—C11—C12	177.90 (17)
O2—N1—C1—C2	5.0 (2)	N5—C10—C11—C16	−0.21 (18)
O1—N1—C1—C2	−173.22 (15)	C16—C11—C12—C13	0.6 (2)
C6—C1—C2—C3	−2.2 (3)	C10—C11—C12—C13	−177.33 (17)
N1—C1—C2—C3	176.39 (16)	C11—C12—C13—C14	−1.3 (2)
C1—C2—C3—C4	1.7 (3)	C12—C13—C14—C15	0.8 (2)
C2—C3—C4—C5	0.6 (3)	C12—C13—C14—N6	179.97 (14)
C2—C3—C4—C7	178.7 (2)	O3—N6—C14—C15	−7.5 (2)
N2—N3—C5—C6	−179.39 (14)	O4—N6—C14—C15	172.00 (16)
C8—N3—C5—C6	13.6 (2)	O3—N6—C14—C13	173.18 (16)
N2—N3—C5—C4	−0.72 (16)	O4—N6—C14—C13	−7.3 (2)
C8—N3—C5—C4	−167.77 (13)	C13—C14—C15—C16	0.6 (2)
C3—C4—C5—N3	178.52 (15)	N6—C14—C15—C16	−178.62 (12)
C7—C4—C5—N3	−0.18 (17)	N5—N4—C16—C15	−179.32 (14)
C3—C4—C5—C6	−2.7 (2)	C9—N4—C16—C15	5.3 (3)
C7—C4—C5—C6	178.62 (14)	N5—N4—C16—C11	−0.53 (15)
C2—C1—C6—C5	0.2 (2)	C9—N4—C16—C11	−175.88 (14)
N1—C1—C6—C5	−178.41 (12)	C14—C15—C16—N4	177.23 (14)
N3—C5—C6—C1	−179.27 (14)	C14—C15—C16—C11	−1.4 (2)
C4—C5—C6—C1	2.2 (2)	C12—C11—C16—N4	−178.06 (13)
N3—N2—C7—C4	−1.5 (2)	C10—C11—C16—N4	0.43 (15)
C3—C4—C7—N2	−177.3 (2)	C12—C11—C16—C15	0.9 (2)
C5—C4—C7—N2	1.1 (2)	C10—C11—C16—C15	179.35 (13)
N2—N3—C8—C9	−78.47 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N5ⁱ	0.93	2.48	3.344 (2)	154
C15—H15···O1ⁱ	0.93	2.47	3.401 (2)	179

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N5ⁱ	0.93	2.48	3.344 (2)	154.4
C15—H15···O1ⁱ	0.93	2.47	3.401 (2)	178.7

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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