Crystal structure of N,N′-bis­(2,4-di­fluoro­benzo­yloxy)benzene-1,2:4,5-tetra­carboximide

Fusco, S.; Tuzi, A.; Centore, R.; Carella, A.

doi:10.1107/S2056989018001226

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ISSN: 2056-9890

Volume 74| Part 2| February 2018| Pages 225-228

https://doi.org/10.1107/S2056989018001226

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Crystal structure of N,N′-bis(2,4-difluorobenzoyloxy)benzene-1,2:4,5-tetracarboximide

Sandra Fusco,^a Angela Tuzi,^a Roberto Centore ^a ^* and Antonio Carella ^a

^aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
^*Correspondence e-mail: roberto.centore@unina.it

Edited by L. Fabian, University of East Anglia, England (Received 8 January 2018; accepted 19 January 2018; online 26 January 2018)

Molecules of the title compound, C₂₄H₈F₄N₂O₈, have C_i point-group symmetry in the crystal, as they lie on crystallographic inversion centres (Z′ = 1/2). The difluorophenyl ring is disordered over two orientations; the final refined occupancy factors of the two components of disorder are 0.947 (4) and 0.053 (4). In the crystal, some C_ar—H⋯F interactions are present, which involve the most acidic H atom of the molecule.

Keywords: crystal structure; imide; weak hydrogen bond; fluorine.

CCDC reference: 1818213

1. Chemical context

Heterocycles are key compounds in synthetic chemistry. In addition to their applications in drugs, bioactive and tautomeric compounds (D'Errico et al., 2012 ; Piccialli et al., 2007 ; Centore et al., 2013 ), aromatic heterocycles play an important role in modern materials chemistry, because they are used as building blocks of active molecules in many emerging fields of advanced materials, for example, conducting polymers (Heeger, 2010 ), organic field-effect transistors (Miao, 2014 ), organic solar cells (Nielsen et al., 2015 ), liquid crystals (Centore et al., 1996 ) and nonlinear optically active compounds (Carella et al., 2007 ; Centore et al., 1999 ).

Aromatic diimides, in particular, are a class of heterocyclic compounds well known for their outstanding properties as n-type organic semiconductors. Very high electron mobilities have been measured for perylenediimides (Schmidt et al., 2007 ) and naphthalenediimides (Yan et al., 2009 ). The research on n-type organic semiconductors has also shown that electron mobilities and device performances can be improved by extensive replacement of H atoms by fluorine (Facchetti et al., 2003 ).

Following these issues, we report here the structural investigation of the title compound, N,N′-bis(2,4-difluorobenzoyloxy)benzene-1,2:4,5-tetracarboximide, which is a fluorinated derivative of the simplest aromatic bis(imide).

2. Structural commentary

Molecules of the title compound in the crystal lie on crystallographic inversion centres and have C_i point-group symmetry. Thus, the asymmetric unit is formed by half a molecule, as shown in Fig. 1. The difluorophenyl ring is disordered over two orientations that differ by a rotation of 180° around the C6—C7 bond. The atomic positions for the two orientations of the difluorophenyl ring are completely superimposed for all atoms, except for the ortho-F atom, for which split positions were observed. The final refined occupancy factors of the two components of disorder are 0.947 (4) and 0.053 (4). Molecules adopt a nonplanar conformation, mainly because of a torsion around the O3—N1 bond. In particular, the pentaatomic ring (atoms C2/C3/C4/N1/C5) is planar within 0.0164 (14) Å, while the phenyl ring (C7/C8a/C9/C10/C11/C12a) is planar within 0.002 (2) Å. The dihedral angle between the mean planes of the two rings is 86.14 (8)°.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. Only the most populated orientation of the disordered difluorophenyl ring is shown. [Symmetry code: (i) −x + 1, −y, −z + 1.]

The C6—O3 bond length [1.402 (3) Å] is significantly longer than the mean value for esters of aromatic acids (1.337 Å; Allen et al., 1987 ). This suggests a reduced contribution of the minor resonance form of the ester group, in which one of the lone pairs of the alkoxy oxygen forms a double bond with the carbonyl C atom that breaks its double bond with the other O atom, thereby giving it a negative charge. This, in turn, can be due to the presence of the electronegative N atom bonded to O3.

3. Supramolecular features

There are weak hydrogen-bond donors (C_ar—H) and strong hydrogen-bond acceptors (carbonyl O atoms) in the title compound. Moreover, F atoms are present as well, whose low hydrogen-bonding-acceptor capability, if any, has been the subject of a long debate in the literature (Dunitz & Taylor, 1997 ; Dunitz, 2004 ). Actually, it is now established that the C—H⋯F interaction is generally weak and does not play a significant structural role in crystal packing when stronger and more polarizable acceptors than the C—F group are present. On the other hand, when the carbon acidity is suitably enhanced, and in the absence of competing acceptors, the (weak) hydrogen-bonding nature of the C—H⋯F interaction is revealed (Thalladi et al., 1998 ).

The most acidic C_ar—H group in the title compound is C9—H, because it has two ortho C—F-group neighbours. It is involved in weak hydrogen-bonding interactions with fluorine, as shown in Fig. 2 and Table 1. In particular, C9—H acts as bifurcated donor to the F1A and F2 atoms. In the first case, R₂²(8) ring motifs are formed across inversion centres. In the second case, chain patterns running parallel to a − b + c/2 are formed. These patterns are quite similar to the supramolecular synthons II and IV reported in the Scheme 2 of Thalladi et al. (1998). It is quite remarkable that significant C—H⋯F interactions are only given by C9—H, which is the most acidic H atom of the molecule.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.95	2.37	3.271 (3)	158
C9—H9⋯F1Aⁱⁱ	0.95	2.51	3.287 (3)	139
C9—H9⋯F2ⁱⁱⁱ	0.95	2.63	3.307 (3)	129
C11—H11⋯O1^iv	0.95	2.39	3.200 (3)	143
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z; (iii) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Partial crystal packing of the title compound, showing the C—H⋯F and C—H⋯O interactions as dashed lines. Only the most populated orientation of the disordered difluorophenyl ring is shown.

Other acidic H atoms are C11—H, because it has one ortho C—F group, and C1—H. They are involved in weak hydrogen-bonding interactions with the O1 and O2 carbonyl acceptors, respectively, see Table 1 and Fig. 2.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.38, last update May 2017; Groom et al., 2016 ) gave no match for the title compound. We have searched for N-oxycarbonylimides using two filters (three-dimensional coordinates determined and not disordered). 47 hits were found. Within this set, 40 hits are N-oxycarbonyl derivatives of succinimide and 6 hits are derivatives of phthalimide. Here follows the full list of refcodes for the CSD search: ADEFUL, AFUXEE, ALOPAU, AWUXOF, BANTOA, CILBUV, COZFOM, DOFTEZ, EABXIO, EABXIO01, FUPPEM, GULRAI, GUVCAB, ICEWIY, LOZFAH, MAMDOU, MILFOE, MIPHUP, MIZJEM, MOZYOQ, NANWUU, OQUPOG, PIGKIZ, SEZWIE, SOSDEK, SUDJIM, SUDWUL, SUDXAS, SUDXAS01, TEQDEY, TUJRIB, UJAFER, UJUBOS, UJUBUY, VALSUZ, WALPEH, WIDKEB, YAFMEY, YAFPOL, YAGBEP, YUJZIN, YUJZOT, ZEPSES, ZEPSIW, ZOQQOL, ZOQQUR, ZALKUV.

The hits found are crystal structures determined at temperatures in the range 90–298 K. In the 47 hits, the N1—O3 distance (DIST1) ranges between 1.375 and 1.408 Å, with an average value of 1.388 (6) Å. On the other hand, the distance O3—C6 (DIST2) is between 1.350 and 1.423 Å, with an average value of 1.393 (15) Å. The histogram of the distribution of DIST1 over the 47 hits found is shown in Fig. 3. The values of DIST1 and DIST2 found in the title compound [N1—O3 = 1.381 (2) Å and O3—C6 = 1.402 (3) Å] are fully consistent with the average values determined from the 47 hits.

Figure 3
Histogram of the N—O bond lengths (DIST1) in the 47 N-oxycarbonylimide hits found in the CSD search.

5. Synthesis and crystallization

N,N′-Dihydroxybenzene-1,2:4,5-tetracarboximide (Centore & Carella, 2013 ) (1.000 g, 4.030 mmol) was suspended in 20 ml of dry pyridine and the system was kept under stirring at room temperature. 2,4-Difluorobenzoylchloride (1.991 g, 11.28 mmol) was added dropwise and the previous suspension turned into a dark solution. The solution was warmed and boiled gently for 45 min. Absolute ethanol (2 ml) and, after 2 min, distilled water (0.2 ml) were then added and the system cooled slowly to room temperature and filtered. The white crystals were washed on the filter with absolute ethanol. From the recovered material it was possible to isolate several single crystals suitable for X-ray analysis. The yield was 55% (m.p. 604 K).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were generated stereochemically and were refined by the riding model. For all H atoms, U_iso(H) = 1.2U_eq(carrier). The difluorophenyl ring is disordered over two orientations, which differ by a rotation of 180° around the phenyl to carbonyl bond. Split positions were only observed for the ortho-F atom. The two split positions were refined by applying SADI restraints on bond lengths. The final refined occupancy factors of the two components of disorder are 0.947 (4) and 0.053 (4).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₈F₄N₂O₈
M_r	528.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	17.100 (6), 4.744 (2), 13.662 (4)
β (°)	106.83 (2)
V (Å³)	1060.8 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.15
Crystal size (mm)	0.40 × 0.15 × 0.01

Data collection
Diffractometer	Bruker–Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )
T_min, T_max	0.931, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	7948, 2396, 1440
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.120, 1.05
No. of reflections	2396
No. of parameters	176
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32
Computer programs: COLLECT (Nonius, 1999 ), DIRAX/LSQ (Duisenberg et al., 2000 ), EVALCCD (Duisenberg et al., 2003 ), SIR97 (Altomare et al., 1999 ), SHELXL2016 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1818213

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989018001226/fy2124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018001226/fy2124Isup2.hkl

checkCIF report

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

N,N'-Bis(2,4-difluorobenzoyloxy)benzene-1,2:4,5-tetracarboximide top

Crystal data top

C₂₄H₈F₄N₂O₈	F(000) = 532
M_r = 528.32	D_x = 1.654 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.100 (6) Å	Cell parameters from 85 reflections
b = 4.744 (2) Å	θ = 5.1–21.4°
c = 13.662 (4) Å	µ = 0.15 mm⁻¹
β = 106.83 (2)°	T = 173 K
V = 1060.8 (7) Å³	Plate, colourless
Z = 2	0.40 × 0.15 × 0.01 mm

Data collection top

Bruker–Nonius KappaCCD diffractometer	2396 independent reflections
Radiation source: normal-focus sealed tube	1440 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
CCD rotation images, thick slices scans	h = −22→21
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −6→6
T_min = 0.931, T_max = 0.986	l = −15→17
7948 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.045P)² + 0.4397P] where P = (F_o² + 2F_c²)/3
2396 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

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 difluorophenyl ring is disordered over two orientations. The two split positions were refined by applying SADI restraints on bond lengths.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.53428 (13)	−0.2108 (5)	0.44840 (16)	0.0196 (5)
H1	0.557147	−0.349497	0.414668	0.024*
C2	0.47095 (12)	−0.0358 (5)	0.39704 (15)	0.0177 (5)
C3	0.43844 (12)	0.1672 (5)	0.44705 (16)	0.0191 (5)
C4	0.37402 (13)	0.3243 (5)	0.36996 (17)	0.0226 (5)
C5	0.42706 (13)	−0.0236 (5)	0.28530 (16)	0.0208 (5)
C6	0.24590 (14)	0.1960 (6)	0.15987 (18)	0.0306 (6)
C7	0.19802 (14)	0.3233 (6)	0.06271 (17)	0.0260 (5)
C9	0.07036 (16)	0.3516 (7)	−0.0723 (2)	0.0406 (7)
H9	0.015390	0.292807	−0.101232	0.049*
C10	0.10527 (16)	0.5453 (7)	−0.11934 (18)	0.0354 (7)
C11	0.18428 (15)	0.6341 (6)	−0.08085 (19)	0.0333 (6)
H11	0.206836	0.769181	−0.116313	0.040*
C8A	0.11781 (16)	0.2431 (6)	0.0194 (2)	0.0369 (7)	0.947 (4)
F1A	0.08458 (11)	0.0511 (5)	0.06620 (15)	0.0714 (8)	0.947 (4)
C12A	0.23029 (14)	0.5223 (6)	0.01072 (18)	0.0289 (6)	0.947 (4)
H12A	0.285205	0.582553	0.038893	0.035*	0.947 (4)
C8B	0.11781 (16)	0.2431 (6)	0.0194 (2)	0.0369 (7)	0.053 (4)
H8B	0.094436	0.108079	0.053933	0.044*	0.053 (4)
C12B	0.23029 (14)	0.5223 (6)	0.01072 (18)	0.0289 (6)	0.053 (4)
F1B	0.3060 (9)	0.615 (6)	0.037 (2)	0.043*	0.053 (4)
F2	0.05967 (10)	0.6562 (4)	−0.20823 (12)	0.0554 (6)
N1	0.37352 (12)	0.1997 (5)	0.27779 (14)	0.0256 (5)
O1	0.33327 (10)	0.5199 (4)	0.38057 (13)	0.0315 (4)
O2	0.43410 (10)	−0.1664 (4)	0.21582 (12)	0.0258 (4)
O3	0.32607 (9)	0.2995 (4)	0.18452 (11)	0.0268 (4)
O4	0.22619 (12)	0.0326 (6)	0.21309 (16)	0.0623 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0185 (10)	0.0213 (12)	0.0195 (10)	0.0013 (10)	0.0062 (8)	0.0007 (10)
C2	0.0187 (10)	0.0186 (12)	0.0162 (9)	−0.0022 (9)	0.0056 (8)	0.0006 (9)
C3	0.0162 (10)	0.0209 (12)	0.0195 (10)	−0.0013 (9)	0.0040 (8)	0.0037 (10)
C4	0.0197 (10)	0.0247 (13)	0.0220 (11)	0.0006 (10)	0.0038 (8)	0.0030 (11)
C5	0.0214 (10)	0.0206 (12)	0.0189 (10)	−0.0006 (10)	0.0037 (8)	0.0034 (10)
C6	0.0236 (12)	0.0388 (16)	0.0262 (12)	−0.0060 (12)	0.0023 (10)	0.0058 (12)
C7	0.0241 (11)	0.0309 (14)	0.0197 (11)	−0.0020 (11)	0.0012 (9)	0.0036 (11)
C9	0.0254 (12)	0.055 (2)	0.0326 (14)	−0.0102 (13)	−0.0051 (10)	0.0056 (14)
C10	0.0307 (13)	0.0479 (18)	0.0209 (11)	0.0052 (13)	−0.0034 (10)	0.0070 (13)
C11	0.0286 (12)	0.0401 (17)	0.0294 (13)	−0.0004 (12)	0.0055 (10)	0.0120 (12)
C8A	0.0308 (13)	0.0423 (17)	0.0331 (14)	−0.0113 (13)	0.0021 (11)	0.0098 (13)
F1A	0.0388 (10)	0.0959 (19)	0.0636 (13)	−0.0361 (11)	−0.0101 (9)	0.0451 (13)
C12A	0.0209 (11)	0.0368 (16)	0.0262 (11)	−0.0034 (11)	0.0021 (9)	0.0042 (12)
C8B	0.0308 (13)	0.0423 (17)	0.0331 (14)	−0.0113 (13)	0.0021 (11)	0.0098 (13)
C12B	0.0209 (11)	0.0368 (16)	0.0262 (11)	−0.0034 (11)	0.0021 (9)	0.0042 (12)
F2	0.0409 (9)	0.0744 (14)	0.0363 (9)	−0.0026 (9)	−0.0119 (7)	0.0227 (9)
N1	0.0271 (10)	0.0289 (12)	0.0162 (9)	0.0073 (9)	−0.0010 (7)	0.0046 (9)
O1	0.0284 (9)	0.0306 (10)	0.0324 (9)	0.0103 (8)	0.0037 (7)	0.0007 (8)
O2	0.0313 (9)	0.0267 (10)	0.0194 (8)	0.0009 (7)	0.0074 (7)	−0.0017 (8)
O3	0.0214 (8)	0.0352 (10)	0.0180 (7)	0.0013 (8)	−0.0035 (6)	0.0083 (8)
O4	0.0424 (12)	0.0860 (19)	0.0466 (12)	−0.0228 (12)	−0.0057 (9)	0.0414 (13)

Geometric parameters (Å, º) top

C1—C2	1.384 (3)	C7—C12A	1.388 (4)
C1—C3ⁱ	1.384 (3)	C9—C10	1.355 (4)
C1—H1	0.9500	C9—C8B	1.379 (4)
C2—C3	1.387 (3)	C9—C8A	1.379 (4)
C2—C5	1.494 (3)	C9—H9	0.9500
C3—C4	1.485 (3)	C10—F2	1.346 (3)
C4—O1	1.194 (3)	C10—C11	1.367 (4)
C4—N1	1.389 (3)	C11—C12B	1.377 (3)
C5—O2	1.200 (3)	C11—C12A	1.377 (3)
C5—N1	1.384 (3)	C11—H11	0.9500
C6—O4	1.177 (3)	C8A—F1A	1.331 (3)
C6—O3	1.402 (3)	C12A—H12A	0.9500
C6—C7	1.472 (3)	C8B—H8B	0.9500
C7—C8B	1.381 (3)	C12B—F1B	1.315 (10)
C7—C8A	1.381 (3)	N1—O3	1.381 (2)
C7—C12B	1.388 (4)

C2—C1—C3ⁱ	114.5 (2)	C10—C9—H9	121.3
C2—C1—H1	122.8	C8A—C9—H9	121.3
C3ⁱ—C1—H1	122.8	F2—C10—C9	118.3 (2)
C1—C2—C3	122.23 (19)	F2—C10—C11	118.5 (3)
C1—C2—C5	129.0 (2)	C9—C10—C11	123.3 (2)
C3—C2—C5	108.78 (19)	C10—C11—C12B	118.2 (2)
C1ⁱ—C3—C2	123.3 (2)	C10—C11—C12A	118.2 (2)
C1ⁱ—C3—C4	128.0 (2)	C10—C11—H11	120.9
C2—C3—C4	108.65 (19)	C12A—C11—H11	120.9
O1—C4—N1	126.2 (2)	F1A—C8A—C9	118.1 (2)
O1—C4—C3	130.0 (2)	F1A—C8A—C7	119.4 (2)
N1—C4—C3	103.76 (19)	C9—C8A—C7	122.5 (2)
O2—C5—N1	126.1 (2)	C11—C12A—C7	121.3 (2)
O2—C5—C2	130.6 (2)	C11—C12A—H12A	119.3
N1—C5—C2	103.36 (19)	C7—C12A—H12A	119.3
O4—C6—O3	121.1 (2)	C9—C8B—C7	122.5 (2)
O4—C6—C7	130.0 (2)	C9—C8B—H8B	118.8
O3—C6—C7	108.8 (2)	C7—C8B—H8B	118.8
C8B—C7—C12B	117.4 (2)	F1B—C12B—C11	112.2 (13)
C8A—C7—C12A	117.4 (2)	F1B—C12B—C7	126.4 (13)
C8B—C7—C6	119.9 (2)	C11—C12B—C7	121.3 (2)
C8A—C7—C6	119.9 (2)	O3—N1—C5	122.00 (19)
C12B—C7—C6	122.7 (2)	O3—N1—C4	122.6 (2)
C12A—C7—C6	122.7 (2)	C5—N1—C4	115.35 (19)
C10—C9—C8B	117.4 (2)	N1—O3—C6	111.96 (18)
C10—C9—C8A	117.4 (2)

C3ⁱ—C1—C2—C3	0.5 (4)	C10—C9—C8A—F1A	−179.5 (3)
C3ⁱ—C1—C2—C5	179.9 (2)	C10—C9—C8A—C7	−0.5 (5)
C1—C2—C3—C1ⁱ	−0.5 (4)	C12A—C7—C8A—F1A	179.5 (3)
C5—C2—C3—C1ⁱ	180.0 (2)	C6—C7—C8A—F1A	0.1 (4)
C1—C2—C3—C4	178.0 (2)	C12A—C7—C8A—C9	0.4 (4)
C5—C2—C3—C4	−1.6 (3)	C6—C7—C8A—C9	−179.0 (3)
C1ⁱ—C3—C4—O1	1.0 (4)	C10—C11—C12A—C7	0.5 (4)
C2—C3—C4—O1	−177.4 (3)	C8A—C7—C12A—C11	−0.4 (4)
C1ⁱ—C3—C4—N1	178.1 (2)	C6—C7—C12A—C11	179.0 (3)
C2—C3—C4—N1	−0.2 (2)	C10—C9—C8B—C7	−0.5 (5)
C1—C2—C5—O2	3.1 (4)	C12B—C7—C8B—C9	0.4 (4)
C3—C2—C5—O2	−177.4 (2)	C6—C7—C8B—C9	−179.0 (3)
C1—C2—C5—N1	−176.8 (2)	C10—C11—C12B—F1B	177.2 (15)
C3—C2—C5—N1	2.7 (2)	C10—C11—C12B—C7	0.5 (4)
O4—C6—C7—C8B	−2.9 (5)	C8B—C7—C12B—F1B	−176.7 (17)
O3—C6—C7—C8B	176.6 (3)	C6—C7—C12B—F1B	2.7 (18)
O4—C6—C7—C8A	−2.9 (5)	C8B—C7—C12B—C11	−0.4 (4)
O3—C6—C7—C8A	176.6 (3)	C6—C7—C12B—C11	179.0 (3)
O4—C6—C7—C12B	177.8 (3)	O2—C5—N1—O3	−6.0 (4)
O3—C6—C7—C12B	−2.7 (4)	C2—C5—N1—O3	173.86 (19)
O4—C6—C7—C12A	177.8 (3)	O2—C5—N1—C4	177.1 (2)
O3—C6—C7—C12A	−2.7 (4)	C2—C5—N1—C4	−3.0 (3)
C8B—C9—C10—F2	−179.2 (3)	O1—C4—N1—O3	2.6 (4)
C8A—C9—C10—F2	−179.2 (3)	C3—C4—N1—O3	−174.73 (19)
C8B—C9—C10—C11	0.6 (5)	O1—C4—N1—C5	179.4 (2)
C8A—C9—C10—C11	0.6 (5)	C3—C4—N1—C5	2.1 (3)
F2—C10—C11—C12B	179.2 (3)	C5—N1—O3—C6	99.6 (3)
C9—C10—C11—C12B	−0.5 (5)	C4—N1—O3—C6	−83.7 (3)
F2—C10—C11—C12A	179.2 (3)	O4—C6—O3—N1	−3.5 (4)
C9—C10—C11—C12A	−0.5 (5)	C7—C6—O3—N1	176.9 (2)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱⁱ	0.95	2.37	3.271 (3)	158
C9—H9···F1Aⁱⁱⁱ	0.95	2.51	3.287 (3)	139
C9—H9···F2^iv	0.95	2.63	3.307 (3)	129
C11—H11···O1^v	0.95	2.39	3.200 (3)	143

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

Acknowledgements

The authors thank the Centro Regionale di Competenza NTAP of Regione Campania (Italy) for the X-ray facility.

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