(1Z,2Z)-1,2-Bis{2-[3,5-bis­(tri­fluoro­meth­yl)phen­yl]hydrazinyl­idene}-1,2-bis­(4-meth­oxy­phen­yl)ethane including an unknown solvate

Akkurt, M.; Shikhaliyev, N.Q.; Askerova, U.F.; Mukhtarova, S.H.; Mammadova, G.Z.; Toze, F.A.A.

doi:10.1107/S2414314619010101

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 7| July 2019| x191010

https://doi.org/10.1107/S2414314619010101

Open

access

(1Z,2Z)-1,2-Bis{2-[3,5-bis(trifluoromethyl)phenyl]hydrazinylidene}-1,2-bis(4-methoxyphenyl)ethane including an unknown solvate

Mehmet Akkurt,^a Namiq Q. Shikhaliyev,^b Ulviyya F. Askerova,^b Sevinc H. Mukhtarova,^b Gunay Z. Mammadova ^b and Flavien A. A. Toze ^c ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bOrganic Chemistry Department, Baku State University, Z. Xalilov str. 23, Az, 1148 Baku, Azerbaijan, and ^cDepartment of Chemistry, Faculty of Sciences, University of Douala, PO Box 24157, Douala, Republic of Cameroon
^*Correspondence e-mail: toflavien@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 9 July 2019; accepted 15 July 2019; online 19 July 2019)

The complete molecule of the title compound, C₃₂H₂₂F₁₂N₄O₂, is generated by a crystallographic twofold axis aligned parallel to [010]. The F atoms of one of the CF₃ groups are disordered over three orientations in a 0.6: 0.2: 0.2 ratio. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming zigzag chains propagating along the a-axis direction. In addition, weak C—H⋯O and C—H⋯F bonds are observed. The contribution of the disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ). Acta Cryst. C71, 9–18] of PLATON. The solvent contribution is not included in the reported molecular weight and density.

Keywords: crystal structure; –CF₃ groups; hydrogen bonding; disorder.

CCDC reference: 1940426

Structure description

In our recent work we have functionalized dye molecules with a C—Cl group, which facilitated halogen bonding (Shixaliyev et al., 2018 , 2019; Atioğlu et al., 2019 ). In a continuation of this work, we have attached –CF₃ groups (potential halogen-bond donor/acceptor sites) to the aromatic moiety of the title hydrazone, C₃₂H₂₂F₁₂N₄O₂, which may lead to C—H⋯F, C—H⋯O, N—H⋯O and C—F⋯F non-covalent interactions in the crystal.

As shown in Fig. 1, the complete molecule is generated by a crystallographic twofold axis passing through the midpoint of the central C—C bond. The bond lengths and the bond angles are comparable to those observed in related structures, for example, 3-methyl-4-[(Z)-2-(4-methylphenyl)hydrazin-1-ylidene]-1-(3-nitrophenyl)-1H-pyrazol-5(4H)-one and 3-methyl-4-[(Z)-2-(4-methylphenyl)hydrazin-1-ylidene]-1-[4-(trifluoromethyl)phenyl]-\1H-pyrazol-5(4H)-one (Alvarez-Thon et al., 2014 ).

Figure 1
The molecular structure of the title compound with displacement ellipsoids for non-H atoms drawn at the 20% probability level. The minor components of the disordered CF₃ group have been omitted.

In the crystal of the title compound, molecules are linked by N2—H2⋯O1(x − $[{1\over 2}]$ , y + $[{1\over 2}]$ ) hydrogen bonds (Table 1; Fig. 2), forming zigzag chains propagating along the a-axis direction. C—H⋯O and C—H⋯F interactions consolidate the packing but π–π stacking and C—H⋯π interactions are not observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.79 (4)	2.32 (4)	3.041 (4)	152 (4)
C3—H3⋯F1"ⁱⁱ	0.95	2.42	3.279 (11)	151
C4—H4⋯F5ⁱⁱⁱ	0.95	2.51	3.439 (4)	165
C14—H14⋯O1ⁱ	0.95	2.57	3.348 (5)	139
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y-1, -z+{\script{3\over 2}}]$ .

Figure 2
Crystal structure of the title compound viewed along the b axis. Dashed lines show hydrogen-bonding interactions. The minor components of the disordered CF₃ group have been omitted.

Synthesis and crystallization

The title compound was synthesized according to the reported method (Atioğlu et al., 2019; Maharramov et al., 2018 ; Shikhaliyev et al., 2018, 2019). A 20 ml screw neck vial was charged with DMSO (10 ml), (E)-1-[3,5-bis(trifluoromethyl)phenyl]-2-(4-methoxybenzylidene)hydrazine (362 mg, 1 mmol), tetramethylethylenediamine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CCl₄ (20 mmol, 10 equiv). After 1–3 h (until TLC analysis showed complete consumption of the corresponding Schiff base), the reaction mixture was poured into 0.01 M HCl (100 ml, pH = 2–3), and extracted with dichloromethane (3 × 20 ml). The combined organic phase was washed with water (3 × 50 ml), brine (30 ml), dried over anhydrous Na₂SO₄ and concentrated in vacuo using a rotary evaporator. The residue was purified by column chromatography on silica gel using appropriate mixtures of hexane and dichloromethane (3/1 − 1/1) giving an orange solid (63%); m.p. 393 K. Analysis calculated for C₃₂H₂₂F₁₂N₄O₂ (M = 722.53): C 53.19, H 3.07, N 7.75; found: C 53.07, H 3.01, N 7.74%. ¹H NMR (300 MHz, CDCl₃) δ 3.89 (6H, 2OCH₃), 7.00–8.23 (14H, Ar). ¹³C NMR (75 MHz, CDCl₃) δ 157.76, 155.49, 148.53, 126.67, 125.49, 119.54, 118.92, 118.66, 118.61, 109.29, 50.67, 25.14. ESI-MS: m/z: 723.44 [M + H]⁺. The title compound was dissolved in dichloromethane and then left at room temperature for slow evaporation; colourless prisms started to form after ca 2 d.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The residual electron density was difficult to model and therefore, the SQUEEZE routine in PLATON (Spek, 2015) was used to remove the contribution of the electron density in the solvent region from the intensity data and the solvent-free model was employed for the final refinement. The solvent formula mass was not taken into account during refinement. The cavity of volume ca 384.5 Å³ (ca 11% of the unit-cell volume) contains approximately 105 electrons. Fifteen outliers (0 2 2), (0 2 3), (1 3 3), (3 3 3), (3 5 4), (4 1 5), (0 12 1), (6 0 6), (1 7 2), (0 6 6), (3 1 8), (6 0 8), (0 4 2), (5 3 2) and (1 0 6) were omitted in the final cycles of refinement. The fluorine atoms of the C15F₃ group are disordered over three orientations in a 0.6: 0.2: 0.2 ratio. Within the disordered CF₃ group, the C—F distances were restrained to 1.330±0.003 Å, and the F—C—F and C—C—F bond angles were limited to near-tetrahedral values by restraining the F⋯F distances to 2.140±0.003 Å. The disordered F atoms (F1 F2 F3 F1′ F2′ F3′ F1" F2" F3") were restrained using the EADP command in SHELX.

Table 2
Experimental details

Crystal data
Chemical formula	C₃₂H₂₂F₁₂N₄O₂
M_r	722.54
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	13.479 (3), 11.213 (2), 22.552 (5)
V (Å³)	3408.5 (12)
Z	4
Radiation type	Synchrotron, λ = 0.78790 Å
μ (mm⁻¹)	0.17
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Rayonix SX165 CCD
Absorption correction	Multi-scan (SCALA; Evans, 2006 )
T_min, T_max	0.954, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	34331, 3971, 2478
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.215, 1.02
No. of reflections	3971
No. of parameters	237
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.56
Computer programs: Marccd (Doyle, 2011 ), iMosflm (Battye et al., 2011 ), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), ORTEP3for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1940426

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010101/hb4306sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619010101/hb4306Isup2.hkl

checkCIF report

Computing details top

Data collection: Marccd (Doyle, 2011); cell refinement: iMosflm (Battye et al., 2011); data reduction: iMosflm (Battye et al., 2011); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP3for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(1Z,2Z)-1,2-Bis{2-[3,5-bis(trifluoromethyl)phenyl]hydrazinylidene}-1,2-bis(4-methoxyphenyl)ethane top

Crystal data top

C₃₂H₂₂F₁₂N₄O₂	D_x = 1.408 Mg m⁻³
M_r = 722.54	Synchrotron radiation, λ = 0.78790 Å
Orthorhombic, Pbcn	Cell parameters from 600 reflections
a = 13.479 (3) Å	θ = 2.0–30.0°
b = 11.213 (2) Å	µ = 0.17 mm⁻¹
c = 22.552 (5) Å	T = 100 K
V = 3408.5 (12) Å³	Prism, colourless
Z = 4	0.18 × 0.12 × 0.10 mm
F(000) = 1464

Data collection top

Rayonix SX165 CCD diffractometer	2478 reflections with I > 2σ(I)
/f scan	R_int = 0.062
Absorption correction: multi-scan (SCALA; Evans, 2006)	θ_max = 31.0°, θ_min = 2.0°
T_min = 0.954, T_max = 0.972	h = −17→17
34331 measured reflections	k = −14→14
3971 independent reflections	l = −29→29

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.215	w = 1/[σ²(F_o²) + (0.08P)² + 4P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3971 reflections	Δρ_max = 0.52 e Å⁻³
237 parameters	Δρ_min = −0.56 e Å⁻³
18 restraints	Extinction correction: SHELXL-2018/1 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.0077 (7)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms of aromatic and methyl groups were placed in calculated positions (C—H = 0.95 and 0.98 Å, respectively) and refined using a riding model withU_iso= 1.2U_eq(C-aromatic) and 1.5U_eq(C-methyl).

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1	0.8573 (3)	0.6496 (2)	0.57941 (18)	0.0832 (7)	0.6
F2	0.8431 (3)	0.5107 (4)	0.51521 (11)	0.0832 (7)	0.6
F3	0.8715 (3)	0.4684 (3)	0.60651 (16)	0.0832 (7)	0.6
F1'	0.8618 (8)	0.6207 (7)	0.6062 (4)	0.0832 (7)	0.2
F2'	0.8426 (8)	0.5731 (9)	0.5152 (2)	0.0832 (7)	0.2
F3'	0.8670 (8)	0.4374 (5)	0.5803 (5)	0.0832 (7)	0.2
F1"	0.8783 (8)	0.5085 (9)	0.6148 (4)	0.0832 (7)	0.2
F2"	0.8552 (7)	0.6378 (6)	0.5458 (5)	0.0832 (7)	0.2
F3"	0.8270 (8)	0.4531 (7)	0.5295 (4)	0.0832 (7)	0.2
F4	0.38927 (16)	0.6493 (2)	0.52250 (11)	0.0811 (7)
F5	0.47074 (18)	0.79502 (19)	0.55878 (11)	0.0837 (7)
F6	0.51490 (18)	0.7197 (2)	0.47565 (11)	0.0857 (7)
O1	0.80893 (17)	−0.1149 (2)	0.84552 (11)	0.0618 (6)
N1	0.59184 (19)	0.2977 (2)	0.70406 (12)	0.0541 (6)
N2	0.5315 (2)	0.3763 (2)	0.67618 (14)	0.0586 (7)
H2	0.474 (3)	0.370 (4)	0.6825 (17)	0.070*
C1	0.5545 (2)	0.2249 (3)	0.74170 (15)	0.0513 (7)
C2	0.6199 (2)	0.1371 (3)	0.77029 (15)	0.0543 (8)
C3	0.5875 (3)	0.0684 (3)	0.81721 (16)	0.0603 (8)
H3	0.5219	0.0796	0.8317	0.072*
C4	0.6476 (3)	−0.0165 (3)	0.84393 (17)	0.0627 (9)
H4	0.6235	−0.0628	0.8761	0.075*
C5	0.7433 (2)	−0.0327 (3)	0.82289 (15)	0.0558 (8)
C6	0.7778 (2)	0.0366 (3)	0.77612 (15)	0.0581 (8)
H6	0.8437	0.0263	0.7621	0.070*
C7	0.7173 (2)	0.1194 (3)	0.75029 (16)	0.0567 (8)
H7	0.7417	0.1659	0.7182	0.068*
C8	0.7725 (3)	−0.1975 (3)	0.88859 (17)	0.0694 (10)
H8A	0.7180	−0.2439	0.8714	0.104*
H8B	0.7485	−0.1538	0.9234	0.104*
H8C	0.8261	−0.2515	0.9005	0.104*
C9	0.5710 (2)	0.4527 (3)	0.63442 (15)	0.0564 (8)
C10	0.6731 (2)	0.4553 (3)	0.62320 (15)	0.0580 (8)
H10	0.7165	0.4028	0.6436	0.070*
C11	0.7098 (3)	0.5348 (3)	0.58237 (16)	0.0610 (8)
C12	0.6496 (3)	0.6129 (3)	0.55145 (16)	0.0627 (9)
H12	0.6768	0.6684	0.5241	0.075*
C13	0.5475 (3)	0.6076 (3)	0.56162 (16)	0.0595 (8)
C14	0.5086 (3)	0.5286 (3)	0.60240 (16)	0.0600 (8)
H14	0.4389	0.5259	0.6088	0.072*
C15	0.8195 (2)	0.5397 (2)	0.57040 (12)	0.0723 (10)
C16	0.4815 (3)	0.6924 (3)	0.52972 (18)	0.0669 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F2	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F3	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F1'	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F2'	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F3'	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F1"	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F2"	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F3"	0.0625 (9)	0.0989 (17)	0.0883 (16)	−0.0094 (12)	0.0081 (11)	0.0227 (13)
F4	0.0686 (13)	0.0683 (13)	0.1064 (17)	0.0058 (11)	−0.0214 (12)	0.0126 (12)
F5	0.0879 (15)	0.0552 (12)	0.1079 (17)	0.0166 (11)	−0.0122 (13)	−0.0034 (12)
F6	0.0849 (15)	0.0845 (16)	0.0877 (16)	0.0244 (13)	0.0063 (13)	0.0265 (12)
O1	0.0574 (13)	0.0502 (12)	0.0779 (15)	0.0070 (10)	−0.0006 (12)	0.0084 (11)
N1	0.0492 (13)	0.0475 (13)	0.0655 (16)	0.0000 (11)	0.0017 (12)	0.0036 (12)
N2	0.0458 (14)	0.0519 (15)	0.0781 (19)	0.0036 (12)	0.0052 (13)	0.0136 (13)
C1	0.0476 (15)	0.0424 (15)	0.0638 (18)	−0.0013 (13)	0.0054 (14)	−0.0024 (13)
C2	0.0501 (16)	0.0450 (15)	0.0677 (19)	−0.0006 (13)	0.0067 (15)	−0.0014 (14)
C3	0.0507 (17)	0.0526 (17)	0.078 (2)	0.0018 (14)	0.0086 (16)	0.0090 (16)
C4	0.0589 (19)	0.0563 (19)	0.073 (2)	0.0023 (16)	0.0088 (17)	0.0146 (16)
C5	0.0529 (17)	0.0455 (16)	0.0691 (19)	0.0036 (13)	−0.0009 (15)	0.0008 (15)
C6	0.0500 (17)	0.0546 (18)	0.070 (2)	0.0044 (14)	0.0083 (15)	0.0011 (16)
C7	0.0509 (17)	0.0499 (16)	0.0692 (19)	0.0015 (14)	0.0098 (15)	0.0064 (15)
C8	0.075 (2)	0.0582 (19)	0.075 (2)	0.0094 (18)	−0.0009 (19)	0.0113 (18)
C9	0.0537 (17)	0.0478 (16)	0.068 (2)	0.0013 (14)	0.0037 (15)	0.0055 (15)
C10	0.0511 (17)	0.0511 (17)	0.072 (2)	−0.0008 (14)	0.0014 (15)	0.0075 (15)
C11	0.0525 (17)	0.0577 (19)	0.073 (2)	−0.0002 (15)	0.0010 (16)	0.0095 (16)
C12	0.063 (2)	0.0541 (18)	0.070 (2)	−0.0006 (16)	0.0032 (17)	0.0106 (16)
C13	0.0610 (19)	0.0474 (16)	0.070 (2)	0.0041 (15)	−0.0047 (17)	0.0054 (15)
C14	0.0524 (17)	0.0525 (18)	0.075 (2)	0.0046 (14)	0.0000 (16)	0.0029 (16)
C15	0.063 (2)	0.071 (2)	0.083 (3)	−0.0008 (18)	0.0034 (19)	0.022 (2)
C16	0.065 (2)	0.0529 (18)	0.083 (3)	0.0053 (16)	−0.0003 (19)	0.0067 (18)

Geometric parameters (Å, º) top

F1—C15	1.349 (3)	C3—C4	1.388 (5)
F2—C15	1.325 (3)	C3—H3	0.9500
F3—C15	1.339 (3)	C4—C5	1.386 (5)
F1'—C15	1.342 (3)	C4—H4	0.9500
F2'—C15	1.336 (3)	C5—C6	1.391 (5)
F3'—C15	1.333 (3)	C6—C7	1.366 (4)
F1"—C15	1.324 (3)	C6—H6	0.9500
F2"—C15	1.323 (3)	C7—H7	0.9500
F3"—C15	1.343 (3)	C8—H8A	0.9800
F4—C16	1.344 (4)	C8—H8B	0.9800
F5—C16	1.332 (4)	C8—H8C	0.9800
F6—C16	1.335 (4)	C9—C14	1.398 (5)
O1—C5	1.375 (4)	C9—C10	1.399 (4)
O1—C8	1.429 (4)	C10—C11	1.373 (5)
N1—C1	1.280 (4)	C10—H10	0.9500
N1—N2	1.355 (4)	C11—C12	1.383 (5)
N2—C9	1.380 (4)	C11—C15	1.504 (4)
N2—H2	0.79 (4)	C12—C13	1.396 (5)
C1—C2	1.471 (4)	C12—H12	0.9500
C1—C1ⁱ	1.516 (6)	C13—C14	1.380 (5)
C2—C3	1.380 (4)	C13—C16	1.488 (5)
C2—C7	1.403 (4)	C14—H14	0.9500

C5—O1—C8	117.7 (3)	C9—C10—H10	120.3
C1—N1—N2	119.1 (3)	C10—C11—C12	122.5 (3)
N1—N2—C9	119.3 (3)	C10—C11—C15	119.9 (3)
N1—N2—H2	116 (3)	C12—C11—C15	117.6 (3)
C9—N2—H2	124 (3)	C11—C12—C13	118.0 (3)
N1—C1—C2	118.8 (3)	C11—C12—H12	121.0
N1—C1—C1ⁱ	123.0 (3)	C13—C12—H12	121.0
C2—C1—C1ⁱ	118.2 (3)	C14—C13—C12	120.7 (3)
C3—C2—C7	117.7 (3)	C14—C13—C16	120.4 (3)
C3—C2—C1	121.3 (3)	C12—C13—C16	118.8 (3)
C7—C2—C1	121.0 (3)	C13—C14—C9	120.4 (3)
C2—C3—C4	122.1 (3)	C13—C14—H14	119.8
C2—C3—H3	119.0	C9—C14—H14	119.8
C4—C3—H3	119.0	F2"—C15—F1"	108.6 (3)
C5—C4—C3	119.0 (3)	F3'—C15—F2'	106.6 (3)
C5—C4—H4	120.5	F2—C15—F3	107.4 (3)
C3—C4—H4	120.5	F3'—C15—F1'	106.1 (3)
O1—C5—C4	124.0 (3)	F2'—C15—F1'	105.7 (3)
O1—C5—C6	116.1 (3)	F2"—C15—F3"	106.6 (3)
C4—C5—C6	119.8 (3)	F1"—C15—F3"	106.5 (3)
C7—C6—C5	120.3 (3)	F2—C15—F1	106.0 (2)
C7—C6—H6	119.9	F3—C15—F1	104.8 (2)
C5—C6—H6	119.9	F2"—C15—C11	117.6 (5)
C6—C7—C2	121.2 (3)	F1"—C15—C11	116.3 (6)
C6—C7—H7	119.4	F2—C15—C11	113.3 (3)
C2—C7—H7	119.4	F3'—C15—C11	114.2 (5)
O1—C8—H8A	109.5	F2'—C15—C11	114.0 (5)
O1—C8—H8B	109.5	F3—C15—C11	112.5 (3)
H8A—C8—H8B	109.5	F1'—C15—C11	109.6 (5)
O1—C8—H8C	109.5	F3"—C15—C11	99.8 (5)
H8A—C8—H8C	109.5	F1—C15—C11	112.2 (3)
H8B—C8—H8C	109.5	F6—C16—F5	106.8 (3)
N2—C9—C14	119.9 (3)	F6—C16—F4	106.5 (3)
N2—C9—C10	121.1 (3)	F5—C16—F4	105.6 (3)
C14—C9—C10	119.0 (3)	F6—C16—C13	112.7 (3)
C11—C10—C9	119.3 (3)	F5—C16—C13	112.3 (3)
C11—C10—H10	120.3	F4—C16—C13	112.4 (3)

C1—N1—N2—C9	−178.3 (3)	C12—C13—C14—C9	0.2 (5)
N2—N1—C1—C2	177.9 (3)	C16—C13—C14—C9	−177.0 (3)
N2—N1—C1—C1ⁱ	−2.0 (5)	N2—C9—C14—C13	178.3 (3)
N1—C1—C2—C3	170.4 (3)	C10—C9—C14—C13	−1.9 (5)
C1ⁱ—C1—C2—C3	−9.6 (5)	C10—C11—C15—F2"	−159.7 (6)
N1—C1—C2—C7	−10.2 (5)	C12—C11—C15—F2"	19.7 (7)
C1ⁱ—C1—C2—C7	169.7 (3)	C10—C11—C15—F1"	−28.4 (6)
C7—C2—C3—C4	−0.6 (5)	C12—C11—C15—F1"	151.0 (6)
C1—C2—C3—C4	178.7 (3)	C10—C11—C15—F2	116.9 (4)
C2—C3—C4—C5	0.1 (6)	C12—C11—C15—F2	−63.7 (4)
C8—O1—C5—C4	7.5 (5)	C10—C11—C15—F3'	27.3 (6)
C8—O1—C5—C6	−172.5 (3)	C12—C11—C15—F3'	−153.3 (6)
C3—C4—C5—O1	−179.4 (3)	C10—C11—C15—F2'	150.2 (6)
C3—C4—C5—C6	0.7 (5)	C12—C11—C15—F2'	−30.4 (6)
O1—C5—C6—C7	179.1 (3)	C10—C11—C15—F3	−5.2 (5)
C4—C5—C6—C7	−0.9 (5)	C12—C11—C15—F3	174.2 (3)
C5—C6—C7—C2	0.4 (5)	C10—C11—C15—F1'	−91.5 (6)
C3—C2—C7—C6	0.4 (5)	C12—C11—C15—F1'	87.9 (6)
C1—C2—C7—C6	−179.0 (3)	C10—C11—C15—F3"	85.6 (6)
N1—N2—C9—C14	175.6 (3)	C12—C11—C15—F3"	−95.0 (6)
N1—N2—C9—C10	−4.1 (5)	C10—C11—C15—F1	−123.2 (4)
N2—C9—C10—C11	−178.3 (3)	C12—C11—C15—F1	56.2 (4)
C14—C9—C10—C11	1.9 (5)	C14—C13—C16—F6	−149.8 (3)
C9—C10—C11—C12	−0.1 (6)	C12—C13—C16—F6	32.9 (5)
C9—C10—C11—C15	179.2 (3)	C14—C13—C16—F5	89.5 (4)
C10—C11—C12—C13	−1.6 (6)	C12—C13—C16—F5	−87.8 (4)
C15—C11—C12—C13	179.0 (3)	C14—C13—C16—F4	−29.5 (5)
C11—C12—C13—C14	1.6 (5)	C12—C13—C16—F4	153.3 (3)
C11—C12—C13—C16	178.8 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱⁱ	0.79 (4)	2.32 (4)	3.041 (4)	152 (4)
C3—H3···F1"ⁱⁱⁱ	0.95	2.42	3.279 (11)	151
C4—H4···F5^iv	0.95	2.51	3.439 (4)	165
C10—H10···F3	0.95	2.37	2.705 (5)	100
C14—H14···O1ⁱⁱ	0.95	2.57	3.348 (5)	139

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

Funding information

This work was supported by the Science Development Foundation under the President of the Republic of Azerbaijan (grant No. EİF/MQM/Elm-Tehsil-1–2016–1(26)–71/06/4).

References

Alvarez-Thon, L., Bustos, C., Molins, E., Garland, M. T. & Baggio, R. (2014). Acta Cryst. C70, 837–842. Web of Science CSD CrossRef IUCr Journals Google Scholar
Atioğlu, Z., Akkurt, M., Shikhaliyev, N. Q., Suleymanova, G. T., Bagirova, K. N. & Toze, F. A. A. (2019). Acta Cryst. E75, 237–241. Web of Science CSD CrossRef IUCr Journals Google Scholar
Battye, T. G. G., Kontogiannis, L., Johnson, O., Powell, H. R. & Leslie, A. G. W. (2011). Acta Cryst. D67, 271–281. Web of Science CrossRef CAS IUCr Journals Google Scholar
Doyle, R. A. (2011). Marccd software manual. Rayonix L. L. C., Evanston, IL 60201, USA. Google Scholar
Evans, P. (2006). Acta Cryst. D62, 72–82. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Maharramov, A. M., Shikhaliyev, N. Q., Suleymanova, G. T., Gurbanov, A. V., Babayeva, G. V., Mammadova, G. Z., Zubkov, F. I., Nenajdenko, V. G., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments, 159, 135–141. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shikhaliyev, N. Q., Ahmadova, N. E., Gurbanov, A. V., Maharramov, A. M., Mammadova, G. Z., Nenajdenko, V. G., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2018). Dyes Pigments, 150, 377–381. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.