3-(2,4-Difluoro­anilino)-9-nitro­dibenzo[b,e]oxepin-11(6H)-one

Baur, B.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536811002881

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o555

doi:10.1107/S1600536811002881

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3-(2,4-Difluoroanilino)-9-nitrodibenzo[b,e]oxepin-11(6H)-one

Benjamin Baur,^a Dieter Schollmeyer ^b and Stefan Laufer ^a ^*

^aInstitute of Pharmacy, Department of Pharmaceutical Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^bDepartment of Organic Chemistry, Johannes Gutenberg-University Mainz, Duessbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 18 January 2011; accepted 21 January 2011; online 2 February 2011)

In the title compound, C₂₀H₁₂F₂N₂O₄, the two benzene rings of the tricyclic unit are oriented at a dihedral angle of 30.6 (1)°. The 2,4-difluoroanilino residue is oriented at a dihedral angle of 68.2 (1)° with respect to the phenoxy ring. In the crystal, N—H⋯O hydrogen bonds between the amino group and the carbonyl O atom of the oxepinone ring link the molecules into infinte chains along the c axis.

Related literature

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004 ). For p38 MAP kinase inhibitors based on dibenzo[b,e]oxepin-11(6H)-one, see: Laufer et al. (2006 ).

Experimental

Crystal data

C₂₀H₁₂F₂N₂O₄
M_r = 382.32
Orthorhombic, P n a 2₁
a = 27.0813 (15) Å
b = 13.0411 (8) Å
c = 4.5998 (2) Å
V = 1624.51 (15) Å³
Z = 4
Cu Kα radiation
μ = 1.08 mm⁻¹
T = 193 K
0.47 × 0.24 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: numerical (CORINC; Dräger & Gattow, 1971 ) T_min = 0.721, T_max = 0.882
3417 measured reflections
3010 independent reflections
2924 reflections with I > 2σ(I)
R_int = 0.051
3 standard reflections every 60 min intensity decay: 3%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.127
S = 1.03
3010 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack, (1983 ), 1270 Friedel pairs
Flack parameter: −0.22 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N16—H16⋯O25ⁱ	0.95	2.32	3.236 (3)	162
Symmetry code: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811002881/im2261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811002881/im2261Isup2.hkl

checkCIF report

Comment top

Based on dibenzo[b,e]oxepin-11(6H)-one (Laufer et al. 2006) as p38 MAP kinase inhibitors, our intent was to synthesize disubstituted oxepin derivatives. The title compound was synthesized in the course of an ongoing study to increase the solubility of the molecules. The structure of the title compound, at 193 K shows orthorhombic symmetry. The two phenyl rings of the tricyclic unit are oriented at a dihedral angle of 30.6 (1°). The 2,4-difluoroanilino residue is oriented at a dihedral angel of 68.2 (1°) towards the phenoxy ring. The crystal stucture is characterized by an intermolecular hydrogen bond N16–H···O25 (2.32 Å).

Related literature top

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004). For p38 MAP kinase inhibitors based on dibenzo[b,e]oxepin-11(6H)-one, see: Laufer et al. (2006).

Experimental top

For the preperation of the title compound a mixture of 200 mg (0.69 mmol) 3-chloro-9-nitrodibenzo[b,e]oxepin-11(6H)-one, 100 mg (0.77 mmol) 2–4-difluoroaniline, 1.00 g (3.07 mmol) Cs₂CO₃, 45 mg (0.10 mmol) 2-(dicyclohexylphosphino)-2`-4`-6`-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc)₂ in 2 ml absolute tert-butanol and 10 ml absolute 2.4-dioxane was stirred for 1 h at 284 K under an argon atmosphere. The mixture was then filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (SiO₂ n-hexane/ethyl acetate 2:1) to get 103 mg (0,27 mmol) of the product as a yellow solid (yield 39 %). Crystals of the title compound were obtained by slow evaporation of diethyl ether and hexane (1:1) at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.

3-(2,4-Difluoroanilino)-9-nitrodibenzo[b,e]oxepin- 11(6H)-one top

Crystal data top

C₂₀H₁₂F₂N₂O₄	F(000) = 784
M_r = 382.32	D_x = 1.563 Mg m⁻³
Orthorhombic, Pna2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 27.0813 (15) Å	θ = 65–69°
b = 13.0411 (8) Å	µ = 1.08 mm⁻¹
c = 4.5998 (2) Å	T = 193 K
V = 1624.51 (15) Å³	Needle, yellow
Z = 4	0.47 × 0.24 × 0.12 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2924 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.051
Graphite monochromator	θ_max = 69.8°, θ_min = 3.3°
ω/2θ scans	h = −33→33
Absorption correction: numerical (CORINC; Dräger & Gattow, 1971)	k = −15→15
T_min = 0.721, T_max = 0.882	l = −5→5
3417 measured reflections	3 standard reflections every 60 min
3010 independent reflections	intensity decay: 3%

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0989P)² + 0.3414P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.023
3010 reflections	Δρ_max = 0.17 e Å⁻³
253 parameters	Δρ_min = −0.20 e Å⁻³
1 restraint	Absolute structure: Flack, (1983), 1270 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.22 (18)

Crystal data top

C₂₀H₁₂F₂N₂O₄	V = 1624.51 (15) Å³
M_r = 382.32	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 27.0813 (15) Å	µ = 1.08 mm⁻¹
b = 13.0411 (8) Å	T = 193 K
c = 4.5998 (2) Å	0.47 × 0.24 × 0.12 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2924 reflections with I > 2σ(I)
Absorption correction: numerical (CORINC; Dräger & Gattow, 1971)	R_int = 0.051
T_min = 0.721, T_max = 0.882	3 standard reflections every 60 min
3417 measured reflections	intensity decay: 3%
3010 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.127	Δρ_max = 0.17 e Å⁻³
S = 1.03	Δρ_min = −0.20 e Å⁻³
3010 reflections	Absolute structure: Flack, (1983), 1270 Friedel pairs
253 parameters	Absolute structure parameter: −0.22 (18)
1 restraint

Special details top

Experimental. ¹H NMR (200 MHz, DMSO-d~6~) δ in p.p.m. 5.32 (s, 2 H), 6.26 (m, 1 H), 6.65 (dd, J=8.65, 1.96 Hz, 1 H), 7.11 (m, 1 H), 7.39 (m, 2 H), 7.82 (m, 1 H), 8.02 (d, J=8.97 Hz, 1 H), 8.41 (dd, J=8.21, 2.53 Hz, 1 H), 8.52 (d, J=2.40 Hz, 1 H), 8.85 (s, NH,1 H).

¹³C NMR (50 MHz, DMSO-d~6~) δ in p.p.m. 72.5, 102.1, 110.5, 116.5, 124.3, 127.0, 130.4, 134.1, 141.1, 142.9, 148.3, 152.9, 163.4, 185.1, C—F not detected.

GC/MS, m/z (%) 382 (100, M⁺), 308 (12), 152 (9), 98 (7), 63 (1).

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	0.58864 (5)	0.24963 (11)	0.3890 (3)	0.0240 (3)
C2	0.56177 (7)	0.30020 (15)	0.5965 (4)	0.0215 (4)
C3	0.51656 (8)	0.25513 (16)	0.6587 (5)	0.0242 (4)
H3	0.5068	0.1947	0.5587	0.029*
C4	0.48548 (8)	0.29789 (17)	0.8665 (5)	0.0245 (4)
C5	0.50161 (8)	0.38484 (16)	1.0212 (5)	0.0242 (4)
H5	0.4818	0.4123	1.1728	0.029*
C6	0.54556 (8)	0.42947 (15)	0.9536 (5)	0.0234 (4)
H6	0.5556	0.4882	1.0605	0.028*
C7	0.57698 (7)	0.39218 (15)	0.7306 (4)	0.0216 (4)
C8	0.61655 (7)	0.46277 (15)	0.6377 (4)	0.0222 (4)
C9	0.65513 (7)	0.43587 (15)	0.4150 (5)	0.0215 (4)
C10	0.68194 (8)	0.51865 (17)	0.3032 (5)	0.0248 (4)
H10	0.6752	0.5865	0.3670	0.030*
C11	0.71823 (7)	0.50081 (16)	0.0997 (5)	0.0262 (5)
C12	0.73012 (8)	0.40368 (18)	0.0000 (5)	0.0275 (5)
H12	0.7551	0.3936	−0.1423	0.033*
C13	0.70420 (7)	0.32175 (17)	0.1161 (5)	0.0253 (5)
H13	0.7120	0.2541	0.0550	0.030*
C14	0.66696 (7)	0.33663 (16)	0.3204 (5)	0.0223 (4)
C15	0.64067 (7)	0.24498 (15)	0.4420 (5)	0.0253 (5)
H15A	0.6542	0.1820	0.3525	0.030*
H15B	0.6466	0.2412	0.6541	0.030*
N16	0.43947 (7)	0.25975 (16)	0.9317 (5)	0.0341 (5)
H16	0.4191	0.3040	1.0435	0.041*
C17	0.41597 (8)	0.18098 (18)	0.7713 (5)	0.0287 (5)
C18	0.37502 (8)	0.20134 (19)	0.5998 (6)	0.0352 (5)
H18	0.3631	0.2697	0.5860	0.042*
C19	0.35112 (10)	0.1240 (2)	0.4481 (7)	0.0434 (6)
H19	0.3226	0.1381	0.3345	0.052*
C20	0.36991 (10)	0.0266 (2)	0.4670 (6)	0.0407 (6)
C21	0.41046 (10)	0.00166 (19)	0.6308 (7)	0.0409 (6)
H21	0.4229	−0.0664	0.6384	0.049*
C22	0.43238 (9)	0.0805 (2)	0.7842 (6)	0.0355 (6)
F23	0.34769 (7)	−0.04940 (15)	0.3148 (5)	0.0629 (6)
F24	0.47133 (6)	0.05902 (13)	0.9539 (5)	0.0558 (5)
O25	0.61751 (6)	0.55042 (11)	0.7364 (4)	0.0302 (4)
N26	0.74461 (7)	0.58919 (15)	−0.0221 (5)	0.0315 (4)
O27	0.73855 (7)	0.67347 (14)	0.0898 (5)	0.0476 (5)
O28	0.77170 (7)	0.57374 (15)	−0.2321 (5)	0.0434 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0251 (7)	0.0263 (7)	0.0205 (8)	−0.0019 (5)	0.0021 (6)	−0.0047 (6)
C2	0.0275 (9)	0.0227 (10)	0.0143 (9)	0.0030 (7)	−0.0011 (8)	0.0020 (8)
C3	0.0306 (10)	0.0249 (10)	0.0171 (10)	−0.0024 (8)	−0.0015 (9)	−0.0011 (8)
C4	0.0270 (10)	0.0287 (10)	0.0179 (11)	−0.0006 (8)	0.0009 (8)	0.0029 (8)
C5	0.0303 (10)	0.0286 (11)	0.0137 (10)	0.0044 (8)	0.0011 (8)	0.0012 (8)
C6	0.0327 (10)	0.0243 (9)	0.0132 (10)	0.0013 (8)	−0.0043 (8)	0.0005 (8)
C7	0.0253 (9)	0.0251 (10)	0.0142 (10)	0.0013 (8)	−0.0036 (8)	0.0021 (8)
C8	0.0271 (9)	0.0210 (9)	0.0184 (10)	0.0019 (7)	−0.0060 (8)	0.0015 (8)
C9	0.0230 (9)	0.0245 (9)	0.0170 (10)	−0.0001 (8)	−0.0063 (8)	0.0033 (8)
C10	0.0283 (10)	0.0227 (9)	0.0234 (11)	−0.0015 (8)	−0.0083 (9)	0.0037 (8)
C11	0.0246 (9)	0.0300 (11)	0.0239 (11)	−0.0059 (8)	−0.0052 (8)	0.0067 (9)
C12	0.0252 (9)	0.0333 (11)	0.0239 (11)	−0.0003 (8)	−0.0023 (9)	0.0038 (9)
C13	0.0256 (9)	0.0261 (10)	0.0241 (11)	0.0017 (8)	−0.0032 (9)	0.0014 (8)
C14	0.0218 (9)	0.0249 (10)	0.0201 (10)	0.0013 (7)	−0.0055 (8)	0.0019 (8)
C15	0.0266 (10)	0.0220 (10)	0.0275 (11)	0.0005 (7)	0.0022 (9)	0.0028 (9)
N16	0.0318 (9)	0.0404 (11)	0.0301 (11)	−0.0050 (8)	0.0088 (9)	−0.0101 (9)
C17	0.0274 (10)	0.0336 (11)	0.0250 (12)	−0.0039 (8)	0.0078 (9)	−0.0015 (9)
C18	0.0338 (11)	0.0355 (13)	0.0363 (14)	0.0036 (9)	0.0046 (10)	−0.0016 (11)
C19	0.0371 (12)	0.0532 (15)	0.0400 (16)	−0.0028 (11)	−0.0025 (12)	−0.0075 (13)
C20	0.0447 (14)	0.0424 (13)	0.0349 (15)	−0.0147 (11)	0.0132 (11)	−0.0110 (11)
C21	0.0444 (12)	0.0287 (12)	0.0495 (16)	−0.0035 (10)	0.0142 (12)	0.0015 (12)
C22	0.0309 (11)	0.0381 (12)	0.0373 (14)	−0.0009 (9)	0.0052 (11)	0.0077 (11)
F23	0.0677 (11)	0.0604 (11)	0.0606 (12)	−0.0257 (9)	0.0120 (10)	−0.0305 (10)
F24	0.0483 (9)	0.0541 (10)	0.0649 (12)	0.0051 (7)	−0.0134 (9)	0.0171 (9)
O25	0.0352 (8)	0.0244 (8)	0.0311 (9)	−0.0034 (6)	0.0017 (7)	−0.0047 (7)
N26	0.0312 (9)	0.0318 (10)	0.0314 (11)	−0.0070 (8)	−0.0010 (9)	0.0060 (9)
O27	0.0584 (11)	0.0300 (9)	0.0545 (13)	−0.0103 (8)	0.0147 (10)	0.0022 (8)
O28	0.0460 (9)	0.0441 (10)	0.0402 (11)	−0.0120 (8)	0.0137 (9)	0.0031 (9)

Geometric parameters (Å, º) top

O1—C2	1.370 (2)	C12—H12	0.9500
O1—C15	1.431 (3)	C13—C14	1.392 (3)
C2—C3	1.388 (3)	C13—H13	0.9500
C2—C7	1.410 (3)	C14—C15	1.499 (3)
C3—C4	1.390 (3)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—N16	1.375 (3)	N16—C17	1.416 (3)
C4—C5	1.408 (3)	N16—H16	0.9504
C5—C6	1.361 (3)	C17—C18	1.387 (3)
C5—H5	0.9500	C17—C22	1.385 (3)
C6—C7	1.419 (3)	C18—C19	1.387 (4)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.476 (3)	C19—C20	1.371 (4)
C8—O25	1.230 (3)	C19—H19	0.9500
C8—C9	1.504 (3)	C20—F23	1.355 (3)
C9—C10	1.399 (3)	C20—C21	1.371 (4)
C9—C14	1.403 (3)	C21—C22	1.381 (4)
C10—C11	1.377 (3)	C21—H21	0.9500
C10—H10	0.9500	C22—F24	1.341 (3)
C11—C12	1.385 (3)	N26—O27	1.225 (3)
C11—N26	1.467 (3)	N26—O28	1.230 (3)
C12—C13	1.385 (3)

C2—O1—C15	115.13 (16)	C12—C13—H13	119.3
O1—C2—C3	114.11 (19)	C14—C13—H13	119.3
O1—C2—C7	123.99 (18)	C13—C14—C9	120.24 (19)
C3—C2—C7	121.85 (19)	C13—C14—C15	119.00 (19)
C2—C3—C4	120.4 (2)	C9—C14—C15	120.75 (19)
C2—C3—H3	119.8	O1—C15—C14	111.72 (16)
C4—C3—H3	119.8	O1—C15—H15A	109.3
N16—C4—C3	123.6 (2)	C14—C15—H15A	109.3
N16—C4—C5	117.53 (19)	O1—C15—H15B	109.3
C3—C4—C5	118.85 (19)	C14—C15—H15B	109.3
C6—C5—C4	120.02 (19)	H15A—C15—H15B	107.9
C6—C5—H5	120.0	C4—N16—C17	123.8 (2)
C4—C5—H5	120.0	C4—N16—H16	115.2
C5—C6—C7	122.89 (19)	C17—N16—H16	117.5
C5—C6—H6	118.6	C18—C17—C22	117.5 (2)
C7—C6—H6	118.6	C18—C17—N16	121.1 (2)
C2—C7—C6	115.63 (18)	C22—C17—N16	121.3 (2)
C2—C7—C8	128.01 (18)	C17—C18—C19	121.4 (2)
C6—C7—C8	115.54 (18)	C17—C18—H18	119.3
O25—C8—C7	119.20 (19)	C19—C18—H18	119.3
O25—C8—C9	116.95 (18)	C20—C19—C18	117.9 (2)
C7—C8—C9	123.78 (18)	C20—C19—H19	121.0
C10—C9—C14	118.6 (2)	C18—C19—H19	121.0
C10—C9—C8	115.52 (18)	F23—C20—C19	118.7 (3)
C14—C9—C8	125.81 (18)	F23—C20—C21	117.8 (3)
C11—C10—C9	119.3 (2)	C19—C20—C21	123.5 (2)
C11—C10—H10	120.3	C20—C21—C22	116.6 (2)
C9—C10—H10	120.3	C20—C21—H21	121.7
C10—C11—C12	123.1 (2)	C22—C21—H21	121.7
C10—C11—N26	118.3 (2)	F24—C22—C21	118.7 (2)
C12—C11—N26	118.6 (2)	F24—C22—C17	118.3 (2)
C11—C12—C13	117.4 (2)	C21—C22—C17	123.0 (2)
C11—C12—H12	121.3	O27—N26—O28	123.8 (2)
C13—C12—H12	121.3	O27—N26—C11	118.7 (2)
C12—C13—C14	121.3 (2)	O28—N26—C11	117.5 (2)

C15—O1—C2—C3	−140.97 (18)	C12—C13—C14—C9	−0.5 (3)
C15—O1—C2—C7	41.3 (3)	C12—C13—C14—C15	−179.1 (2)
O1—C2—C3—C4	179.62 (18)	C10—C9—C14—C13	−0.9 (3)
C7—C2—C3—C4	−2.6 (3)	C8—C9—C14—C13	−178.83 (19)
C2—C3—C4—N16	177.5 (2)	C10—C9—C14—C15	177.64 (19)
C2—C3—C4—C5	−2.8 (3)	C8—C9—C14—C15	−0.3 (3)
N16—C4—C5—C6	−176.1 (2)	C2—O1—C15—C14	−88.1 (2)
C3—C4—C5—C6	4.2 (3)	C13—C14—C15—O1	−121.5 (2)
C4—C5—C6—C7	−0.2 (3)	C9—C14—C15—O1	59.9 (3)
O1—C2—C7—C6	−176.19 (18)	C3—C4—N16—C17	−8.2 (4)
C3—C2—C7—C6	6.3 (3)	C5—C4—N16—C17	172.1 (2)
O1—C2—C7—C8	14.7 (3)	C4—N16—C17—C18	−110.1 (3)
C3—C2—C7—C8	−162.8 (2)	C4—N16—C17—C22	71.2 (3)
C5—C6—C7—C2	−4.9 (3)	C22—C17—C18—C19	0.4 (4)
C5—C6—C7—C8	165.57 (19)	N16—C17—C18—C19	−178.4 (2)
C2—C7—C8—O25	162.9 (2)	C17—C18—C19—C20	−1.5 (4)
C6—C7—C8—O25	−6.2 (3)	C18—C19—C20—F23	−178.5 (2)
C2—C7—C8—C9	−14.0 (3)	C18—C19—C20—C21	1.0 (4)
C6—C7—C8—C9	176.95 (17)	F23—C20—C21—C22	−179.9 (2)
O25—C8—C9—C10	−11.8 (3)	C19—C20—C21—C22	0.6 (4)
C7—C8—C9—C10	165.16 (18)	C20—C21—C22—F24	178.1 (2)
O25—C8—C9—C14	166.2 (2)	C20—C21—C22—C17	−1.8 (4)
C7—C8—C9—C14	−16.9 (3)	C18—C17—C22—F24	−178.6 (2)
C14—C9—C10—C11	1.4 (3)	N16—C17—C22—F24	0.1 (3)
C8—C9—C10—C11	179.54 (17)	C18—C17—C22—C21	1.3 (4)
C9—C10—C11—C12	−0.6 (3)	N16—C17—C22—C21	−179.9 (2)
C9—C10—C11—N26	177.82 (18)	C10—C11—N26—O27	10.3 (3)
C10—C11—C12—C13	−0.8 (3)	C12—C11—N26—O27	−171.3 (2)
N26—C11—C12—C13	−179.2 (2)	C10—C11—N26—O28	−169.8 (2)
C11—C12—C13—C14	1.3 (3)	C12—C11—N26—O28	8.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16···O25ⁱ	0.95	2.32	3.236 (3)	162

Symmetry code: (i) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₂F₂N₂O₄
M_r	382.32
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	193
a, b, c (Å)	27.0813 (15), 13.0411 (8), 4.5998 (2)
V (Å³)	1624.51 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.47 × 0.24 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Numerical (CORINC; Dräger & Gattow, 1971)
T_min, T_max	0.721, 0.882
No. of measured, independent and observed [I > 2σ(I)] reflections	3417, 3010, 2924
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.127, 1.03
No. of reflections	3010
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20
Absolute structure	Flack, (1983), 1270 Friedel pairs
Absolute structure parameter	−0.22 (18)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16···O25ⁱ	0.95	2.32	3.236 (3)	162

Symmetry code: (i) −x+1, −y+1, z+1/2.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. (2004). J. Org. Chem. 69, 4936–4947 Web of Science CrossRef PubMed CAS Google Scholar
Laufer, S. A., Ahrens, G. M., Karcher, S. C., Hering, J. S. & Niess, R. (2006). J. Med. Chem. 49, 7912–7915. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Page o555

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