2-(4-Methyl­phen­yl)-1H-anthraceno[1,2-d]imidazole-6,11-dione: a fluorescent chemosensor

Guimarães, T.T.; Da Silva Júnior, E.N.; Carvalho, C.E.M.; De Simone, C.A.; Pinto, A.V.

doi:10.1107/S1600536809013634

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1063

doi:10.1107/S1600536809013634

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2-(4-Methylphenyl)-1H-anthraceno[1,2-d]imidazole-6,11-dione: a fluorescent chemosensor

Tiago T. Guimarães,^a Eufrânio N. Da Silva Júnior,^b Carlos Eduardo M. Carvalho,^c Carlos A. De Simone ^d ^* and Antonio V. Pinto ^a

^aNúcleo de Pesquisas em Produtos Naturais, Universidade Federal do Rio de Janeiro, 21944-971 Rio de Janeiro, RJ, Brazil, ^bInstituto de Química, Universidade de Brasília, 70910-970 Brasília, DF, Brazil, ^cUniversidade Estadual da Zona Oeste (UEZO), 23070-200 Rio de Janeiro, RJ, Brazil, and ^dInstituto de Física de São Carlos, Universidade de São Paulo – USP, 13560-970 São Carlos, SP, Brazil
^*Correspondence e-mail: casimone@ifsc.usp.br

(Received 6 April 2009; accepted 10 April 2009; online 18 April 2009)

In the title compound, C₂₂H₁₄N₂O₂, the five rings of the molecule are not coplanar. There is a significant twist between the four fused rings, which have a slightly arched conformation, and the pendant aromatic ring, as seen in the dihedral angle of 13.16 (8)° between the anthraquinonic ring system and the pendant aromatic ring plane.

Related literature

For general background on organic fluorophores, see: Czarnik (1994 ); Friend et al. (1999 ); Joux & Lebaron (2000 ); Kasten (1999 ); Soukos et al. (2000 ); Zhu et al. (2008 ). For related structures and applications, see: Peng et al. (2005 ); Boiocchi et al. (2004 ); Yoshida et al. (2002 ).

Experimental

Crystal data

C₂₂H₁₄N₂O₂
M_r = 338.35
Orthorhombic, P b c a
a = 7.3850 (10) Å
b = 14.0730 (4) Å
c = 30.5630 (9) Å
V = 3176.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.14 × 0.14 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
20847 measured reflections
3643 independent reflections
2282 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.155
S = 1.05
3643 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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 I, global. DOI: 10.1107/S1600536809013634/tk2418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013634/tk2418Isup2.hkl

checkCIF report

Comment top

Recently, much attention has been devoted to the study of organic fluorophores because of their potential use in analytical chemistry (Czarnik, 1994), optoeletronics (Friend et al., 1999), dye technologies (Joux & Lebaron, 1988; Kasten, 1999), forensic chemistry (Soukos et al., 2000), and in pharmaceutical analysis evaluations (Zhu et al., 2008). In addition, specific and sensitive chemosensors for anions are of great importance in environmental science (Peng et al., 2005). The N—H···F interaction is already well known (Boiocchi et al., 2004) and can be exploited in the development of new molecules to function as fluorescent probes for fluoride. For instance, one such class of probe are the anthraimidazolic-derived quinones that can be deprotonated in the presence of anions to enhance their natural fluorescence by a supposed mechanism of photo-induced electron transfer (PET) or via a bathochromic shift of the absorption bands promoted by charge transfer (CT) (Peng et al., 2005). Although many photophysical properties of fluorophores are well known in solution, only a few are known in solid-state (Yoshida et al., 2002). In this paper we report the molecular structure of the 2-p-tolyl-1H-anthra[1,2-d]imidazole-6,11-dione, (I), a fluorescent probe synthesized in our laboratory.

In (I), the rings are not co-planar (Fig. 1). The anthraquinonic ring is almost planar with the greatest deviation from the least-squares plane of 0.102 (2) Å being exhibited by atom C7. The dihedral angle between the anthraquinonic ring [C2—C11] and the benzene ring [C12—C17] planes is 13.16 (8)°.

Related literature top

For general background on organic

fluorophores, see: Czarnik (1994); Friend et al. (1999); Joux & Lebaron (1988); Kasten (1999); Soukos et al. (2000); Zhu et al. (2008). For related structures and applications, see: Peng et al. (2005); Boiocchi et al. (2004); Yoshida et al. (2002).

Experimental top

To an acetic acid solution (25 ml) of the 1,2-diaminoanthraquinone (238 mg, 1 mmol), p-methyl-benzaldehyde (132 mg, 1.1 mmol) and sodium acetate (107 mg, 1.3 mmol) were added. The mixture was left under agitation and reflux for 30 min. The reaction was leaked into cold water (50 ml) which precipitated a yellow solid that was filtered under vacuum. The new anthraimidazole derivate (I) was purified by column chromatography over silica-gel, using a dichloromethane/ethyl acetate (5:1) mixture as eluent and obtained as yellow crystals in 69.5% yield (235 mg, 0.70 mmol); m.p. 522 K. ¹H NMR (300 MHz, CDCl₃) δ: 8.33–8.30 (m, 1H); 8.27–8.24 (m, 1H); 8.20 (d, J = 8.79 Hz, 1H); 8.08 (d, J = 7.91 Hz, 2H); 8.03 (d, J = 8.79 Hz, 1H); 7.83–7.75 (m, 2H); 7.37 (d, J = 7.91 Hz, 2H); 2.46 p.p.m. (s, 3H); N—H not obs. ¹³C NMR (300 MHz, CDCl₃): δ: 21.8, 117.82, 121.87, 125.40, 125.74, 126.37, 126.79, 126.91, 127.48, 128.35, 129.91, 129.91, 133.14, 133.23, 133.63, 133.94, 134.29, 141.94, 149.53, 156.78, 183.1, 183.1 p.p.m.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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. Projection of (I), showing the atom labelling with 50% probability displacement ellipsoids.

2-(4-Methylphenyl)-1H-anthraceno[1,2-d]imidazole-6,11-dione top

Crystal data top

C₂₂H₁₄N₂O₂	F(000) = 1408
M_r = 338.35	D_x = 1.415 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14527 reflections
a = 7.385 (1) Å	θ = 2.9–27.5°
b = 14.0730 (4) Å	µ = 0.09 mm⁻¹
c = 30.5630 (9) Å	T = 295 K
V = 3176.4 (4) Å³	Prism, yellow
Z = 8	0.14 × 0.14 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	2282 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.066
Horizonally mounted graphite crystal monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 9 pixels mm^-1	h = −9→7
CCD rotation images, thick slices scans	k = −14→18
20847 measured reflections	l = −39→38
3643 independent 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0589P)² + 1.2992P] where P = (F_o² + 2F_c²)/3
3643 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₂H₁₄N₂O₂	V = 3176.4 (4) Å³
M_r = 338.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.385 (1) Å	µ = 0.09 mm⁻¹
b = 14.0730 (4) Å	T = 295 K
c = 30.5630 (9) Å	0.14 × 0.14 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	2282 reflections with I > 2σ(I)
20847 measured reflections	R_int = 0.066
3643 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.05	Δρ_max = 0.18 e Å⁻³
3643 reflections	Δρ_min = −0.20 e Å⁻³
235 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	0.7524 (2)	0.58882 (10)	0.24672 (5)	0.0537 (4)
O2	0.4748 (2)	0.25831 (11)	0.30424 (6)	0.0632 (5)
N1	0.6678 (2)	0.53709 (11)	0.16053 (6)	0.0413 (4)
H1N	0.7063	0.5904	0.1706	0.050*
N2	0.5832 (2)	0.42641 (11)	0.11186 (6)	0.0454 (4)
C1	0.6423 (3)	0.51458 (14)	0.11723 (7)	0.0420 (5)
C2	0.5674 (3)	0.39056 (14)	0.15381 (7)	0.0420 (5)
C3	0.5055 (3)	0.30226 (14)	0.16831 (8)	0.0480 (5)
H3	0.4709	0.2556	0.1484	0.058*
C4	0.4967 (3)	0.28566 (14)	0.21264 (8)	0.0476 (5)
H4	0.4546	0.2272	0.2225	0.057*
C4A	0.5494 (3)	0.35426 (13)	0.24325 (7)	0.0406 (5)
C5	0.5310 (3)	0.33481 (15)	0.29076 (8)	0.0454 (5)
C5A	0.5811 (3)	0.41206 (14)	0.32185 (7)	0.0440 (5)
C6	0.5545 (3)	0.39803 (18)	0.36653 (8)	0.0567 (6)
H6	0.5056	0.3412	0.3766	0.068*
C7	0.6007 (3)	0.46845 (19)	0.39578 (8)	0.0632 (7)
H7	0.5787	0.4597	0.4255	0.076*
C8	0.6794 (3)	0.55197 (18)	0.38151 (8)	0.0621 (7)
H8	0.7133	0.5982	0.4016	0.075*
C9	0.7077 (3)	0.56666 (16)	0.33750 (8)	0.0506 (6)
H9	0.7609	0.6228	0.3279	0.061*
C9A	0.6566 (3)	0.49753 (14)	0.30745 (7)	0.0420 (5)
C10	0.6808 (3)	0.51561 (14)	0.26033 (7)	0.0399 (5)
C10A	0.6161 (3)	0.44294 (13)	0.22942 (7)	0.0380 (5)
C11	0.6208 (3)	0.45918 (13)	0.18450 (7)	0.0381 (5)
C12	0.6719 (3)	0.58162 (14)	0.08136 (7)	0.0428 (5)
C13	0.7054 (3)	0.67704 (15)	0.08847 (8)	0.0504 (6)
H13	0.7151	0.6997	0.1170	0.060*
C14	0.7245 (3)	0.73941 (16)	0.05371 (8)	0.0558 (6)
H14	0.7481	0.8032	0.0593	0.067*
C15	0.7090 (3)	0.70857 (17)	0.01088 (8)	0.0526 (6)
C16	0.6790 (3)	0.61297 (17)	0.00396 (8)	0.0595 (6)
H16	0.6702	0.5904	−0.0246	0.071*
C17	0.6617 (3)	0.55016 (16)	0.03836 (8)	0.0560 (6)
H17	0.6429	0.4860	0.0327	0.067*
C18	0.7200 (4)	0.7767 (2)	−0.02702 (9)	0.0722 (8)
H18A	0.8401	0.8026	−0.0287	0.108*
H18B	0.6345	0.8273	−0.0228	0.108*
H18C	0.6926	0.7437	−0.0537	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0679 (10)	0.0417 (8)	0.0517 (10)	−0.0081 (7)	−0.0037 (8)	−0.0011 (7)
O2	0.0776 (11)	0.0491 (9)	0.0630 (11)	−0.0064 (8)	0.0067 (9)	0.0101 (8)
N1	0.0463 (9)	0.0352 (9)	0.0424 (11)	−0.0031 (7)	−0.0018 (8)	−0.0024 (8)
N2	0.0500 (10)	0.0411 (10)	0.0452 (11)	0.0008 (8)	0.0006 (8)	−0.0064 (8)
C1	0.0414 (11)	0.0418 (11)	0.0427 (13)	0.0036 (9)	−0.0024 (9)	−0.0058 (10)
C2	0.0402 (10)	0.0403 (11)	0.0456 (12)	0.0030 (9)	−0.0003 (9)	−0.0045 (10)
C3	0.0529 (13)	0.0362 (11)	0.0550 (15)	−0.0020 (9)	0.0011 (11)	−0.0098 (10)
C4	0.0491 (12)	0.0351 (11)	0.0586 (15)	−0.0019 (9)	0.0037 (11)	−0.0012 (10)
C4A	0.0379 (10)	0.0360 (10)	0.0478 (13)	0.0042 (8)	0.0018 (9)	0.0012 (10)
C5	0.0398 (11)	0.0414 (12)	0.0550 (14)	0.0047 (9)	0.0035 (10)	0.0074 (10)
C5A	0.0382 (11)	0.0488 (12)	0.0452 (13)	0.0075 (9)	−0.0030 (9)	0.0022 (10)
C6	0.0529 (13)	0.0672 (15)	0.0499 (15)	0.0062 (11)	0.0004 (11)	0.0078 (13)
C7	0.0656 (15)	0.0835 (19)	0.0405 (14)	0.0123 (14)	−0.0019 (12)	0.0012 (13)
C8	0.0679 (16)	0.0670 (16)	0.0515 (16)	0.0107 (13)	−0.0098 (12)	−0.0144 (13)
C9	0.0547 (13)	0.0490 (12)	0.0482 (14)	0.0087 (10)	−0.0067 (11)	−0.0057 (11)
C9A	0.0400 (11)	0.0428 (11)	0.0432 (13)	0.0098 (9)	−0.0037 (9)	−0.0006 (10)
C10	0.0391 (10)	0.0338 (10)	0.0468 (13)	0.0044 (9)	−0.0032 (9)	0.0005 (9)
C10A	0.0344 (10)	0.0369 (10)	0.0426 (12)	0.0051 (8)	0.0004 (8)	−0.0027 (9)
C11	0.0369 (10)	0.0341 (10)	0.0435 (12)	0.0013 (8)	−0.0002 (9)	−0.0029 (9)
C12	0.0431 (11)	0.0441 (12)	0.0412 (12)	0.0005 (9)	0.0005 (9)	−0.0028 (10)
C13	0.0598 (14)	0.0479 (13)	0.0434 (13)	−0.0037 (10)	−0.0031 (10)	−0.0052 (10)
C14	0.0656 (15)	0.0490 (13)	0.0526 (15)	−0.0101 (11)	−0.0020 (11)	0.0014 (11)
C15	0.0445 (12)	0.0649 (15)	0.0484 (14)	−0.0049 (11)	0.0024 (10)	0.0066 (12)
C16	0.0709 (16)	0.0690 (16)	0.0387 (13)	−0.0046 (13)	0.0007 (11)	−0.0036 (12)
C17	0.0713 (15)	0.0505 (13)	0.0463 (14)	−0.0040 (11)	0.0021 (11)	−0.0087 (11)
C18	0.0713 (17)	0.0866 (19)	0.0587 (17)	−0.0103 (14)	−0.0009 (13)	0.0207 (15)

Geometric parameters (Å, º) top

O1—C10	1.231 (2)	C7—H7	0.9300
O2—C5	1.225 (2)	C8—C9	1.377 (3)
N1—C11	1.364 (2)	C8—H8	0.9300
N1—C1	1.374 (3)	C9—C9A	1.390 (3)
N1—H1N	0.8600	C9—H9	0.9300
N2—C1	1.325 (2)	C9A—C10	1.473 (3)
N2—C2	1.383 (3)	C10—C10A	1.472 (3)
C1—C12	1.463 (3)	C10A—C11	1.392 (3)
C2—C3	1.396 (3)	C12—C13	1.383 (3)
C2—C11	1.403 (3)	C12—C17	1.389 (3)
C3—C4	1.376 (3)	C13—C14	1.385 (3)
C3—H3	0.9300	C13—H13	0.9300
C4—C4A	1.399 (3)	C14—C15	1.384 (3)
C4—H4	0.9300	C14—H14	0.9300
C4A—C10A	1.407 (3)	C15—C16	1.380 (3)
C4A—C5	1.484 (3)	C15—C18	1.506 (3)
C5—C5A	1.491 (3)	C16—C17	1.380 (3)
C5A—C6	1.393 (3)	C16—H16	0.9300
C5A—C9A	1.397 (3)	C17—H17	0.9300
C6—C7	1.378 (3)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.382 (3)	C18—H18C	0.9600

C11—N1—C1	107.29 (16)	C9—C9A—C5A	120.2 (2)
C11—N1—H1N	126.4	C9—C9A—C10	119.47 (19)
C1—N1—H1N	126.4	C5A—C9A—C10	120.34 (19)
C1—N2—C2	104.75 (17)	O1—C10—C10A	120.28 (19)
N2—C1—N1	112.35 (18)	O1—C10—C9A	121.81 (19)
N2—C1—C12	124.07 (19)	C10A—C10—C9A	117.91 (18)
N1—C1—C12	123.55 (18)	C11—C10A—C4A	116.79 (18)
N2—C2—C3	130.29 (19)	C11—C10A—C10	120.72 (18)
N2—C2—C11	110.19 (17)	C4A—C10A—C10	122.48 (19)
C3—C2—C11	119.5 (2)	N1—C11—C10A	131.92 (18)
C4—C3—C2	118.6 (2)	N1—C11—C2	105.41 (18)
C4—C3—H3	120.7	C10A—C11—C2	122.65 (18)
C2—C3—H3	120.7	C13—C12—C17	117.9 (2)
C3—C4—C4A	121.86 (19)	C13—C12—C1	122.37 (19)
C3—C4—H4	119.1	C17—C12—C1	119.70 (19)
C4A—C4—H4	119.1	C12—C13—C14	120.9 (2)
C4—C4A—C10A	120.6 (2)	C12—C13—H13	119.6
C4—C4A—C5	120.09 (18)	C14—C13—H13	119.6
C10A—C4A—C5	119.33 (18)	C15—C14—C13	121.2 (2)
O2—C5—C4A	121.5 (2)	C15—C14—H14	119.4
O2—C5—C5A	120.7 (2)	C13—C14—H14	119.4
C4A—C5—C5A	117.81 (18)	C16—C15—C14	117.6 (2)
C6—C5A—C9A	119.1 (2)	C16—C15—C18	120.8 (2)
C6—C5A—C5	119.1 (2)	C14—C15—C18	121.6 (2)
C9A—C5A—C5	121.8 (2)	C17—C16—C15	121.5 (2)
C7—C6—C5A	119.9 (2)	C17—C16—H16	119.2
C7—C6—H6	120.0	C15—C16—H16	119.2
C5A—C6—H6	120.0	C16—C17—C12	120.8 (2)
C6—C7—C8	120.8 (2)	C16—C17—H17	119.6
C6—C7—H7	119.6	C12—C17—H17	119.6
C8—C7—H7	119.6	C15—C18—H18A	109.5
C9—C8—C7	120.0 (2)	C15—C18—H18B	109.5
C9—C8—H8	120.0	H18A—C18—H18B	109.5
C7—C8—H8	120.0	C15—C18—H18C	109.5
C8—C9—C9A	120.0 (2)	H18A—C18—H18C	109.5
C8—C9—H9	120.0	H18B—C18—H18C	109.5
C9A—C9—H9	120.0

C2—N2—C1—N1	0.8 (2)	C5A—C9A—C10—C10A	2.6 (3)
C2—N2—C1—C12	−177.41 (18)	C4—C4A—C10A—C11	2.0 (3)
C11—N1—C1—N2	−0.6 (2)	C5—C4A—C10A—C11	−176.46 (17)
C11—N1—C1—C12	177.64 (18)	C4—C4A—C10A—C10	−177.16 (18)
C1—N2—C2—C3	177.6 (2)	C5—C4A—C10A—C10	4.4 (3)
C1—N2—C2—C11	−0.7 (2)	O1—C10—C10A—C11	−5.4 (3)
N2—C2—C3—C4	−177.4 (2)	C9A—C10—C10A—C11	174.48 (17)
C11—C2—C3—C4	0.8 (3)	O1—C10—C10A—C4A	173.70 (18)
C2—C3—C4—C4A	−0.6 (3)	C9A—C10—C10A—C4A	−6.4 (3)
C3—C4—C4A—C10A	−0.9 (3)	C1—N1—C11—C10A	−178.3 (2)
C3—C4—C4A—C5	177.60 (18)	C1—N1—C11—C2	0.1 (2)
C4—C4A—C5—O2	2.1 (3)	C4A—C10A—C11—N1	176.36 (19)
C10A—C4A—C5—O2	−179.44 (19)	C10—C10A—C11—N1	−4.5 (3)
C4—C4A—C5—C5A	−177.22 (18)	C4A—C10A—C11—C2	−1.8 (3)
C10A—C4A—C5—C5A	1.2 (3)	C10—C10A—C11—C2	177.34 (17)
O2—C5—C5A—C6	−3.3 (3)	N2—C2—C11—N1	0.4 (2)
C4A—C5—C5A—C6	176.00 (18)	C3—C2—C11—N1	−178.13 (17)
O2—C5—C5A—C9A	175.73 (19)	N2—C2—C11—C10A	179.00 (17)
C4A—C5—C5A—C9A	−5.0 (3)	C3—C2—C11—C10A	0.5 (3)
C9A—C5A—C6—C7	0.7 (3)	N2—C1—C12—C13	169.3 (2)
C5—C5A—C6—C7	179.74 (19)	N1—C1—C12—C13	−8.7 (3)
C5A—C6—C7—C8	−2.3 (3)	N2—C1—C12—C17	−8.8 (3)
C6—C7—C8—C9	1.9 (4)	N1—C1—C12—C17	173.16 (19)
C7—C8—C9—C9A	0.1 (3)	C17—C12—C13—C14	1.2 (3)
C8—C9—C9A—C5A	−1.7 (3)	C1—C12—C13—C14	−177.0 (2)
C8—C9—C9A—C10	177.59 (19)	C12—C13—C14—C15	0.7 (4)
C6—C5A—C9A—C9	1.3 (3)	C13—C14—C15—C16	−1.8 (3)
C5—C5A—C9A—C9	−177.70 (18)	C13—C14—C15—C18	176.8 (2)
C6—C5A—C9A—C10	−178.00 (18)	C14—C15—C16—C17	1.1 (3)
C5—C5A—C9A—C10	3.0 (3)	C18—C15—C16—C17	−177.5 (2)
C9—C9A—C10—O1	3.2 (3)	C15—C16—C17—C12	0.7 (4)
C5A—C9A—C10—O1	−177.51 (18)	C13—C12—C17—C16	−1.9 (3)
C9—C9A—C10—C10A	−176.75 (17)	C1—C12—C17—C16	176.3 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄N₂O₂
M_r	338.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	7.385 (1), 14.0730 (4), 30.5630 (9)
V (Å³)	3176.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.14 × 0.14 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20847, 3643, 2282
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.155, 1.05
No. of reflections	3643
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

This work has received partial support from CNPq, FAPERJ, CAPES, FAPEAL, IM–INOFAR, USP and FINEP.

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