Crystal structure of 2,7-dieth-oxy-1,8-bis-(4-nitro-benzo-yl)naphthalene.

The title compound, C28H22N2O8, possesses crystallographically imposed twofold symmetry, with the two central carbon atoms of the naphthalene unit lying on the rotation axis. The two benzoyl groups in the mol-ecule are twisted away from the attached naphthalene unit with a C-C-C=O torsion angle of 49.05 (15)° between the naphthalene unit and the carbonyl group. The dihedral angle between the naphthalene ring system and the benzene ring is 77.17 (5)°. In the crystal, pairs of C-H⋯O=C hydrogen bonds link the mol-ecules into a double-column structure along the c axis. The mol-ecules are further linked by C-H⋯O=N hydrogen bonds, forming a three-dimensional network. C-H⋯π inter-actions between the methyl-ene group and the naphthalene unit and π-π inter-actions between the naphthalene ring systems [centroid-centroid distances of 3.7858 (7)-3.7860 (7) Å] are also observed.

Chemical context

Mol­ecules with non-coplanarly accumulated aromatic rings, such as biphenyl and binaphthyl derivatives, have been in the limelight as unique building blocks affording characteristic optical and electronic properties (Hatano et al., 2013 ▶; Park et al., 2010 ▶; Vaghi et al., 2013 ▶) and asymmetric mol­ecular environments (Bulman Page et al., 2012 ▶; Jayalakshmi et al., 2012 ▶; Kano et al., 2006 ▶; Wang et al., 2014 ▶). peri-Substituted naphthalenes have also much attention as characteristic aromatic ring core compounds and the structural analyses have been actively performed (Cohen et al., 2004 ▶; Jing et al., 2005 ▶).

In the course of our study on selective electrophilic aromatic aroylation of 2,7-di­meth­oxy­n class="Chemical">naphthalene, peri-aroyl­naphthalene compounds have proved to be formed regio­selectively with the aid of a suitable acidic mediator (Okamoto & Yonezawa, 2009 ▶; Okamoto et al., 2011 ▶). According to X-ray crystal analysis, the resulting 1,8-diaroyl­naphthalene and 1-monoaroyl­naphthalene compounds have non-coplanarly accumulated aromatic-ring structures in their crystals. The aroyl groups at the 1,8-positions (or 1-position) of the naphthalene ring system in the mol­ecules are situated in a perpendicular fashion to the naphthalene ring system, as shown in 1,8-dibenzoyl-2,7-di­meth­oxy­naphthalene (Nakaema et al., 2008 ▶), 1,8-dibenzoyl-2,7-di­eth­oxy­naphthalene (Isogai et al., 2013 ▶) and 1-(4-nitro­benzo­yl)-2,7-di­meth­oxy­naphthalene (Watanabe et al., 2010 ▶). As a part of our continuous study on the mol­ecular structures of this kind of mol­ecules, the X-ray crystal structure of the title compound is reported here.

Structural commentary

The title mol­ecule lies on a crystallographic twofold axis running through atoms C5 and C6 of the n class="Chemical">naphthalene unit so that the asymmetric unit consists of one half-mol­ecule (Fig. 1 ▶). In the mol­ecule, two aroyl groups are non-coplanarly attached to the naphthalene ring system. The torsion angles of the benzene ring and the naphthalene ring system with the ketonic carbonyl moiety (O1—C7—C8—C13 and C6—C1—C7—O1) are 26.83 (17) and 49.05 (15)°, respectively. The dihedral angle between the benzene ring and the naphthalene ring system is 77.17 (5)°. The benzene ring and the nitro group are approximately coplanar with a dihedral angle of 5.0 (2)°.

Figure 1

The mol­ecular structure of the title compound with the atom numbering. The displacement ellipsoids are drawn at the 50% probability level.

Supra­molecular features

In the crystal, the mol­ecular packing of the title compound is mainly stabilized by a pair of C—H⋯O=C hydrogen bonds between the n class="Chemical">benzene ring and the ketonic carbonyl group (C13—H13⋯O1i; details and symmetry code in Table 1 ▶), which make an (10) ring motif (Fig. 2 ▶). The mol­ecules are stacked through these inter­actions in a double-column along the c axis. The mol­ecules are also linked by C—H⋯O=N inter­actions between the benzene ring and the nitro group (C10—H10⋯O3ii; Table 1 ▶), forming a three-dimensional network and thus resulting in the inter­penetration of the naphthalene unit into the adjacent double-column. π–π inter­actions between the inter­penetrating naphthalene ring systems are observed; the inter­planar distance is 3.5326 (4) Å and the centroid–centroid distances are 3.7860 (7), 3.7859 (7) and 3.7858 (7) Å, respectively, for Cg1⋯Cg1vi, Cg1⋯Cg2vii and Cg2⋯Cg2viii, where Cg1 and Cg2 are the centroids of the six-membered C1–C6 and C1v–C4v/C5/C6 rings, respectively [symmetry codes: (v) −x + 1, y, −z + ; (vi) −x + 1, −y + 1, −z; (vii) x, −y + 1, z − ; (viii) −x + 1, −y + 1, −z + 1]. C—H⋯π inter­actions between the methyl­ene group and the naphthalene ring system (C14—H14B⋯Cg1iii and C14—H14B⋯Cg2iv; Table 1 ▶ and Fig. 3 ▶) are also observed.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the six-membered C1–C6 and C1v–C4v/C5/C6 rings, respectively. [Symmetry code: (v) −x + 1, y, −z + .]

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.95	2.50	3.2129 (17)	132
C10—H10⋯O3ii	0.95	2.59	3.360 (2)	138
C14—H14B⋯Cg1iii	0.99	2.81	3.6284 (15)	140
C14—H14B⋯Cg2iv	0.99	2.81	3.6284 (15)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 2

A crystal packing view of the title compound, showing the inter­molecular C—H⋯O=C and C—H⋯O=N inter­actions. [Symmetry codes: (i) 1 − x, −y, −z; (ii)  − x,  + y,  − z.]

Figure 3

A crystal packing view of the title compound, showing the inter­molecular C—H⋯π inter­actions (dashed lines) and π–π inter­actions (double dashed lines).

Database survey

A search of the Cambridge Structural Database (Version 5.35, last update May 2014; Allen, 2002 ▶) showed 39 and 29 structures containing the 1,8-diaroyl­naphthalene (including 1,8-dialkanoyl­n class="Chemical">naphthalene) and 1,8-diaroyl-2,7-di­alk­oxy­naph­thal­ene units, respectively. The title compound has a non-coplanarly accumulated aromatic-rings structure, as found in the nitro group-free 1,8-di­benzoyl­naphthalene homologues and the nitro-group-bearing 1-benzoyl­naphthalene homologue, viz. 1,8-dibenzoyl-2,7-di­meth­oxy­naphthalene (Naka­ema et al., 2008 ▶) and 1,8-dibenzoyl-2,7-di­eth­oxy­naphthalene (Isogai et al., 2013 ▶), and 2,7-dimeth­oxy-1-(4-nitro­benzo­yl)naphthalene (Watanabe et al., 2010 ▶). The dihedral angle between the benzene ring and the naphthalene ring system [77.17 (5)°] is close to those of the three homologues [68.42 (5) and 71.69 (5)° for 1,8-dibenzoyl-2,7-di­eth­oxy­naphthalene; 83.59 (5)° for 1,8-dibenzoyl-2,7-di­meth­oxy­naphthalene; 61.97 (5)° for 1-(4-nitro­benzo­yl)-2,7-di­meth­oxy­naphthalene]. On the other hand, the torsion angle between the carbonyl group and the benzene ring is different from the homologues, i.e., the title compound [26.83 (17)°] > 1-(4-nitro­benzo­yl)-2,7-di­meth­oxy­naphthalene [−13.29 (17)°] >> 1,8-dibenzoyl-2,7-di­eth­oxy­naphthalene [1.58 (17)° and 1.44 (17)°] > 1,8-dibenzoyl-2,7-di­meth­oxy­naphthalene [0.4 (2)°]. Although the C—H⋯O=C inter­actions between the benzene ring and the ketonic carbonyl group are observed in all of four homologues, the C—H⋯O=N inter­action is observed only in the title compound.

Synthesis and crystallization

To a 10 ml flask, 4-nitro­benzoic acid (3.96 mmol, 735 mg), n class="Chemical">aluminium chloride (4.35 mmol, 580 mg) and methyl chloride (3.0 ml) were placed and stirred at 273 K. To reaction mixture thus obtained, 2,7-di­eth­oxy­naphthalene (0.6 mmol, 130 mg) was added. After the reaction mixture was stirred at 273 K for 48 h, it was poured into ice-cold water (10 ml). The aqueous layer was extracted with CHCl3 (10 ml×3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give cake. The crude product was purified by reprecipitation (CHCl3/methanol) (isolated yield 27%). Finally, the isolated product was crystallized from CHCl3-hexane (v/v = 2:1) to give single crystals.

1H NMR (300 MHz, CDCl3): δ 0.91 (6H, t, J = 5.2 Hz), 3.98 (4H, q, J = 5.2 Hz), 7.18 (2H, d, J = 6.9 Hz), 7.91 (4H, d, J = 6.6 Hz), 8.00 (2H, d, J = 6.9 Hz), 8.26 (4H, d, J = 6.6 Hz); 13C n class="Chemical">NMR (75 MHz, CDCl3): δ 14.39, 64.90, 111.96, 119.88, 123.50, 125.48, 129.74, 130.82, 133.44, 144.19, 150.06, 156.77, 197.28; IR (KBr cm−1): 1662 (C=O), 1603, 1515, 1472 (Ar, naphthalene), 1229 (=C—O—C); HRMS (m/z): [M + H]+ Calculated for C28H22N2O8, 515.1410; found, 515.1449; m.p. = 556.4–568.5 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▶. All H atoms were located in a difference Fourier map and were subsequently refined as riding atoms, with C—H = 0.95 (aromatic), 0.98 (meth­yl) and 0.99 Å (methyl­ene), and with U iso(H) = 1.2U eq(C). The positions of methyl n class="Disease">H atoms were rotationally optimized.

Table 2

Experimental details

Crystal data
Chemical formula	C28H22N2O8
M r	514.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	23.5359 (16), 10.2522 (5), 10.3605 (11)
β (°)	97.257 (14)
V (Å3)	2479.9 (3)
Z	4
Radiation type	Cu Kα
μ (mm−1)	0.86
Crystal size (mm)	0.50 × 0.40 × 0.20
Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999 ▶)
T min, T max	0.674, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	21420, 2272, 2118
R int	0.044
(sin θ/λ)max (Å−1)	0.602
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.037, 0.101, 1.02
No. of reflections	2272
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.21, −0.26

Computer programs: PROCESS-AUTO (Rigaku, 1998 ▶), CrystalStructure (Rigaku, 2010 ▶), SIR2004 (Burla et al., 2007 ▶), SHELXL97 (Sheldrick, 2008 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018674/is5370sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018674/is5370Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018674/is5370Isup3.pdf

Supporting information file. DOI: 10.1107/S1600536814018674/is5370Isup4.pdf

Supporting information file. DOI: 10.1107/S1600536814018674/is5370Isup5.pdf

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018674/is5370Isup6.cml

CCDC reference: 1019755

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H22N2O8	F(000) = 1072
Mr = 514.48	Dx = 1.378 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -C 2yc	Cell parameters from 1640 reflections
a = 23.5359 (16) Å	θ = 3.8–67.5°
b = 10.2522 (5) Å	µ = 0.86 mm−1
c = 10.3605 (11) Å	T = 193 K
β = 97.257 (14)°	Block, yellow
V = 2479.9 (3) Å3	0.50 × 0.40 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2272 independent reflections
Radiation source: rotating anode	2118 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.8°
ω scans	h = −28→27
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.674, Tmax = 0.847	l = −12→12
21420 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0552P)2 + 1.320P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2272 reflections	Δρmax = 0.21 e Å−3
175 parameters	Δρmin = −0.26 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: 0.0031 (2)

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.

	x	y	z	Uiso*/Ueq
O1	0.48373 (3)	0.18553 (8)	0.10345 (8)	0.0365 (2)
O2	0.60134 (4)	0.37631 (9)	0.01960 (9)	0.0428 (3)
O3	0.72391 (7)	−0.19473 (16)	0.10952 (14)	0.0991 (6)
O4	0.76491 (5)	−0.08350 (14)	0.27145 (16)	0.0812 (4)
N1	0.72522 (6)	−0.10377 (14)	0.18632 (14)	0.0584 (4)
C1	0.53601 (5)	0.37563 (12)	0.16932 (11)	0.0305 (3)
C2	0.57104 (5)	0.44716 (13)	0.09761 (11)	0.0347 (3)
C3	0.57153 (5)	0.58479 (13)	0.10108 (12)	0.0397 (3)
H3	0.5962	0.6327	0.0528	0.048*
C4	0.53620 (5)	0.64790 (13)	0.17435 (12)	0.0396 (3)
H4	0.5359	0.7406	0.1746	0.048*
C5	0.5000	0.58029 (16)	0.2500	0.0346 (4)
C6	0.5000	0.44053 (16)	0.2500	0.0303 (4)
C7	0.53051 (5)	0.23260 (12)	0.14003 (11)	0.0306 (3)
C8	0.58275 (5)	0.14797 (11)	0.15282 (11)	0.0325 (3)
C9	0.63069 (5)	0.17560 (12)	0.24136 (12)	0.0368 (3)
H9	0.6313	0.2522	0.2932	0.044*
C10	0.67737 (5)	0.09281 (13)	0.25474 (13)	0.0415 (3)
H10	0.7099	0.1102	0.3164	0.050*
C11	0.67537 (6)	−0.01629 (13)	0.17554 (14)	0.0422 (3)
C12	0.62879 (6)	−0.04532 (13)	0.08520 (14)	0.0455 (3)
H12	0.6288	−0.1204	0.0314	0.055*
C13	0.58214 (6)	0.03741 (13)	0.07495 (13)	0.0410 (3)
H13	0.5494	0.0187	0.0143	0.049*
C14	0.64361 (6)	0.43699 (15)	−0.04805 (14)	0.0458 (3)
H14A	0.6698	0.4913	0.0121	0.055*
H14B	0.6252	0.4930	−0.1193	0.055*
C15	0.67573 (7)	0.32734 (18)	−0.10160 (18)	0.0615 (4)
H15A	0.6952	0.2756	−0.0297	0.074*
H15B	0.7041	0.3631	−0.1535	0.074*
H15C	0.6488	0.2717	−0.1567	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.0325 (5)	0.0357 (5)	0.0403 (5)	−0.0042 (3)	0.0003 (3)	−0.0047 (4)
O2	0.0451 (5)	0.0403 (5)	0.0458 (5)	−0.0028 (4)	0.0167 (4)	0.0027 (4)
O3	0.1189 (12)	0.1059 (12)	0.0720 (9)	0.0757 (10)	0.0100 (8)	−0.0127 (8)
O4	0.0517 (7)	0.0739 (9)	0.1132 (11)	0.0221 (6)	−0.0077 (7)	0.0084 (8)
N1	0.0580 (8)	0.0581 (8)	0.0623 (8)	0.0231 (6)	0.0198 (7)	0.0154 (7)
C1	0.0301 (6)	0.0293 (6)	0.0306 (6)	−0.0002 (4)	−0.0027 (5)	0.0010 (4)
C2	0.0338 (6)	0.0353 (7)	0.0338 (6)	−0.0014 (5)	−0.0004 (5)	0.0012 (5)
C3	0.0414 (7)	0.0351 (7)	0.0418 (7)	−0.0071 (5)	0.0024 (5)	0.0071 (5)
C4	0.0463 (7)	0.0276 (6)	0.0427 (7)	−0.0031 (5)	−0.0033 (6)	0.0033 (5)
C5	0.0370 (9)	0.0294 (9)	0.0349 (8)	0.000	−0.0050 (7)	0.000
C6	0.0304 (8)	0.0282 (8)	0.0300 (8)	0.000	−0.0047 (6)	0.000
C7	0.0327 (6)	0.0323 (6)	0.0266 (5)	−0.0025 (5)	0.0024 (4)	−0.0004 (5)
C8	0.0334 (6)	0.0291 (6)	0.0354 (6)	−0.0036 (5)	0.0058 (5)	−0.0004 (5)
C9	0.0364 (6)	0.0340 (7)	0.0393 (6)	−0.0015 (5)	0.0024 (5)	−0.0027 (5)
C10	0.0346 (7)	0.0444 (8)	0.0447 (7)	0.0002 (5)	0.0017 (5)	0.0042 (6)
C11	0.0394 (7)	0.0388 (7)	0.0507 (7)	0.0082 (5)	0.0140 (6)	0.0090 (6)
C12	0.0502 (8)	0.0351 (7)	0.0528 (8)	0.0026 (6)	0.0129 (6)	−0.0074 (6)
C13	0.0385 (7)	0.0377 (7)	0.0464 (7)	−0.0029 (5)	0.0036 (5)	−0.0085 (6)
C14	0.0384 (7)	0.0536 (8)	0.0463 (7)	−0.0059 (6)	0.0094 (6)	0.0084 (6)
C15	0.0469 (8)	0.0731 (11)	0.0686 (10)	0.0035 (7)	0.0238 (7)	0.0044 (8)

O1—C7	1.2181 (14)	C7—C8	1.4970 (16)
O2—C2	1.3546 (15)	C8—C13	1.3903 (17)
O2—C14	1.4298 (15)	C8—C9	1.3904 (17)
O3—N1	1.224 (2)	C9—C10	1.3813 (18)
O4—N1	1.2188 (19)	C9—H9	0.9500
N1—C11	1.4698 (17)	C10—C11	1.385 (2)
C1—C2	1.3872 (17)	C10—H10	0.9500
C1—C6	1.4278 (14)	C11—C12	1.381 (2)
C1—C7	1.4997 (17)	C12—C13	1.3809 (19)
C2—C3	1.4116 (19)	C12—H12	0.9500
C3—C4	1.3584 (19)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.500 (2)
C4—C5	1.4105 (15)	C14—H14A	0.9900
C4—H4	0.9500	C14—H14B	0.9900
C5—C4i	1.4105 (15)	C15—H15A	0.9800
C5—C6	1.433 (2)	C15—H15B	0.9800
C6—C1i	1.4278 (14)	C15—H15C	0.9800
C2—O2—C14	120.70 (11)	C10—C9—C8	120.65 (12)
O4—N1—O3	123.69 (14)	C10—C9—H9	119.7
O4—N1—C11	118.84 (14)	C8—C9—H9	119.7
O3—N1—C11	117.46 (15)	C9—C10—C11	118.03 (12)
C2—C1—C6	120.28 (12)	C9—C10—H10	121.0
C2—C1—C7	116.77 (10)	C11—C10—H10	121.0
C6—C1—C7	122.12 (11)	C12—C11—C10	122.71 (12)
O2—C2—C1	115.43 (11)	C12—C11—N1	118.54 (13)
O2—C2—C3	123.23 (11)	C10—C11—N1	118.75 (13)
C1—C2—C3	121.22 (12)	C11—C12—C13	118.37 (12)
C4—C3—C2	119.13 (12)	C11—C12—H12	120.8
C4—C3—H3	120.4	C13—C12—H12	120.8
C2—C3—H3	120.4	C12—C13—C8	120.41 (12)
C3—C4—C5	122.13 (12)	C12—C13—H13	119.8
C3—C4—H4	118.9	C8—C13—H13	119.8
C5—C4—H4	118.9	O2—C14—C15	105.65 (12)
C4i—C5—C4	121.13 (16)	O2—C14—H14A	110.6
C4i—C5—C6	119.43 (8)	C15—C14—H14A	110.6
C4—C5—C6	119.43 (8)	O2—C14—H14B	110.6
C1—C6—C1i	124.45 (15)	C15—C14—H14B	110.6
C1—C6—C5	117.77 (7)	H14A—C14—H14B	108.7
C1i—C6—C5	117.77 (7)	C14—C15—H15A	109.5
O1—C7—C1	120.12 (10)	C14—C15—H15B	109.5
O1—C7—C8	119.87 (11)	H15A—C15—H15B	109.5
C1—C7—C8	120.00 (9)	C14—C15—H15C	109.5
C13—C8—C9	119.81 (12)	H15A—C15—H15C	109.5
C13—C8—C7	118.22 (11)	H15B—C15—H15C	109.5
C9—C8—C7	121.96 (11)
C14—O2—C2—C1	−173.03 (10)	C2—C1—C7—C8	58.11 (14)
C14—O2—C2—C3	10.93 (18)	C6—C1—C7—C8	−132.34 (10)
C6—C1—C2—O2	−176.93 (8)	O1—C7—C8—C13	26.83 (17)
C7—C1—C2—O2	−7.18 (14)	C1—C7—C8—C13	−151.79 (11)
C6—C1—C2—C3	−0.81 (16)	O1—C7—C8—C9	−151.86 (12)
C7—C1—C2—C3	168.94 (11)	C1—C7—C8—C9	29.52 (17)
O2—C2—C3—C4	174.63 (11)	C13—C8—C9—C10	−1.34 (19)
C1—C2—C3—C4	−1.18 (18)	C7—C8—C9—C10	177.33 (11)
C2—C3—C4—C5	1.68 (18)	C8—C9—C10—C11	1.42 (19)
C3—C4—C5—C4i	179.81 (13)	C9—C10—C11—C12	−0.4 (2)
C3—C4—C5—C6	−0.19 (13)	C9—C10—C11—N1	178.57 (12)
C2—C1—C6—C1i	−177.76 (11)	O4—N1—C11—C12	−175.30 (14)
C7—C1—C6—C1i	13.05 (7)	O3—N1—C11—C12	3.6 (2)
C2—C1—C6—C5	2.24 (11)	O4—N1—C11—C10	5.7 (2)
C7—C1—C6—C5	−166.95 (7)	O3—N1—C11—C10	−175.35 (14)
C4i—C5—C6—C1	178.24 (8)	C10—C11—C12—C13	−0.8 (2)
C4—C5—C6—C1	−1.76 (8)	N1—C11—C12—C13	−179.72 (12)
C4i—C5—C6—C1i	−1.76 (8)	C11—C12—C13—C8	0.9 (2)
C4—C5—C6—C1i	178.24 (8)	C9—C8—C13—C12	0.2 (2)
C2—C1—C7—O1	−120.50 (12)	C7—C8—C13—C12	−178.56 (12)
C6—C1—C7—O1	49.05 (15)	C2—O2—C14—C15	169.06 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1ii	0.95	2.50	3.2129 (17)	132
C10—H10···O3iii	0.95	2.59	3.360 (2)	138
C14—H14B···Cg1iv	0.99	2.81	3.6284 (15)	140
C14—H14B···Cg2v	0.99	2.81	3.6284 (15)	140