N-[3-(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo­hepten-2-ylamino)phen­yl]furan-3-carboxamide

Dorn, A.; Schollmeyer, D.; Laufer, S.A.

doi:10.1107/S1600536810013450

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1100

https://doi.org/10.1107/S1600536810013450

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N-[3-(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-ylamino)phenyl]furan-3-carboxamide

Angelika Dorn,^a Dieter Schollmeyer ^b and Stefan A. Laufer ^a ^*

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

(Received 9 March 2010; accepted 12 April 2010; online 17 April 2010)

In the title compound, C₂₆H₂₀N₂O₃, the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 54.53 (9)°. The crystal structure displays intermolecular N—H⋯O hydrogen bonding.

Related literature

For palladium-catalyzed amination reactions of aryl halides with anilines, see: Jensen et al. (2004 ); Grasa et al. (2001 ). For p38 inhibitors based on dibenzosuberones, see: Laufer et al. (2006 ).

Experimental

Crystal data

C₂₆H₂₀N₂O₃
M_r = 408.44
Monoclinic, P 2₁ /c
a = 10.7691 (7) Å
b = 21.746 (1) Å
c = 8.8666 (6) Å
β = 101.934 (2)°
V = 2031.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII diffractometer
22214 measured reflections
4856 independent reflections
3347 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.115
S = 0.99
4856 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯O16ⁱ	0.87	2.14	2.900 (2)	146
N24—H24⋯O26ⁱⁱ	0.91	2.00	2.839 (2)	153
Symmetry codes: (i) x, y, z-1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536810013450/im2187sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013450/im2187Isup2.hkl

checkCIF report

Comment top

p38 mitogen activated protein (MAP) kinase is a key enzyme in inflammatory diseases as it is involved in the biosynthesis of proinflammatory cytokines such as TNF-α and IL-1β (Laufer et al. 2006). Small molecule p38 inhibitors suppress the production of these cytokines and therefore p38 is an attractive and promising drug target for novel anti-inflammatory therapeutics (Laufer et al. 2006). Recently, we designed and synthesized a series of p38 inhibitors based on dibenzosuberones (Laufer et al. 2006). The title compound was prepared in the course of our studies on dibenzo[a,d]cycloheptan-5-ones as potent p38 MAP kinase inhibitors.

The structure of the title compound, at 173 (2) K has monoclinic (P2₁/c) symmetry. In the molecule (Fig.1), rings A (C1—C4, C14, C15) and B (C6—C11) are, of course, planar and they are oriented at a dihedral angle of A/B = 54.53 (9)°. The intramolecular C21—H21···O26 (2.66 Å) interaction stabilizes the conformation of the molecule. In the crystal structure the hydrogen bonds N17—H17···O16 (2.90 Å) and N24—H24···O26 (2.84 Å) link the molecule into double layers.

Related literature top

For palladium-catalysed amination reactions of aryl halides with anilines, see: Jensen et al. (2004); Grasa et al. (2001). For p38 inhibitors based on dibenzosuberones, see: Laufer et al. (2006).

Experimental top

For the preparation of the title compound a mixture of 500 mg (2.1 mmol) 2-chloro-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one, 420 mg (2.1 mmol) N-(3-aminophenyl)-3-furamide, 940 mg (8.4 mmol) KOtert-Bu, 90 mg (0.19 mmol) 2-(dicyclohexylphosphino)-2'-, 4'-, 6'-triisopropylbiphenyl and 20 mg (0.09 mmol) Pd(OAc)₂ in 3 ml absolute tert-butanol and 7 ml absolute toluol was stirred for 4 h at 363 K under an atmosphere of argon. The mixture was diluted with water and then extracted with ethyl acetate. The extracts were combined, washed with saturated saline solution, dried over Na₂SO₄ and then evaporated under reduced pressure. The residue was purified by flash chromatography (SiO₂ 60, n-hexane / ethyl acetate 3 + 2) (yield: 17.2 %). Crystals of the title compound were obtained by slow evaporation of a methanol / diethyl ether solution at room temperature.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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.
	Fig. 2. Part of the crystal packing showing the supramoleculare structure. View along the a-axis.

N-[3-(5-Oxo-10,11-dihydro-5H- dibenzo[a,d]cyclohepten-2-ylamino)phenyl]furan-3-carboxamide top

Crystal data top

C₂₆H₂₀N₂O₃	F(000) = 856
M_r = 408.44	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3910 reflections
a = 10.7691 (7) Å	θ = 2.5–25.8°
b = 21.746 (1) Å	µ = 0.09 mm⁻¹
c = 8.8666 (6) Å	T = 173 K
β = 101.934 (2)°	Plate, yellow
V = 2031.6 (2) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	3347 reflections with I > 2σ(I)
Radiation source: sealed Tube	R_int = 0.044
Graphite monochromator	θ_max = 27.9°, θ_min = 1.9°
CCD scan	h = −14→14
22214 measured reflections	k = −28→28
4856 independent reflections	l = −11→11

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0358P)² + 1.2737P] where P = (F_o² + 2F_c²)/3
4856 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₆H₂₀N₂O₃	V = 2031.6 (2) Å³
M_r = 408.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7691 (7) Å	µ = 0.09 mm⁻¹
b = 21.746 (1) Å	T = 173 K
c = 8.8666 (6) Å	0.30 × 0.20 × 0.10 mm
β = 101.934 (2)°

Data collection top

Bruker SMART APEXII diffractometer	3347 reflections with I > 2σ(I)
22214 measured reflections	R_int = 0.044
4856 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 0.99	Δρ_max = 0.24 e Å⁻³
4856 reflections	Δρ_min = −0.30 e Å⁻³
280 parameters

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. 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
C1	0.33786 (17)	0.51791 (8)	0.78886 (19)	0.0268 (4)
C2	0.35431 (17)	0.55527 (8)	0.92028 (19)	0.0282 (4)
H2	0.3714	0.5979	0.9131	0.034*
C3	0.34553 (17)	0.52992 (8)	1.05935 (19)	0.0278 (4)
H3	0.3579	0.5559	1.1474	0.033*
C4	0.31908 (16)	0.46745 (8)	1.07779 (18)	0.0255 (4)
C5	0.30193 (18)	0.45074 (8)	1.23480 (19)	0.0293 (4)
C6	0.23344 (17)	0.39443 (8)	1.26987 (19)	0.0306 (4)
C7	0.15301 (19)	0.40150 (10)	1.3739 (2)	0.0394 (5)
H7	0.1435	0.4409	1.4166	0.047*
C8	0.0873 (2)	0.35182 (12)	1.4151 (3)	0.0521 (6)
H8	0.0319	0.3572	1.4847	0.063*
C9	0.1023 (2)	0.29455 (11)	1.3551 (3)	0.0528 (6)
H9	0.0572	0.2603	1.3834	0.063*
C10	0.1828 (2)	0.28669 (10)	1.2539 (2)	0.0420 (5)
H10	0.1932	0.2469	1.2141	0.050*
C11	0.24914 (18)	0.33624 (8)	1.2092 (2)	0.0323 (4)
C12	0.3358 (2)	0.32699 (8)	1.0986 (2)	0.0359 (4)
H12A	0.3430	0.2825	1.0788	0.043*
H12B	0.4215	0.3425	1.1458	0.043*
C13	0.2882 (2)	0.36007 (8)	0.9458 (2)	0.0345 (4)
H13A	0.3316	0.3422	0.8680	0.041*
H13B	0.1964	0.3514	0.9118	0.041*
C14	0.30687 (17)	0.42898 (8)	0.94687 (19)	0.0269 (4)
C15	0.31629 (17)	0.45534 (8)	0.80680 (19)	0.0272 (4)
H15	0.3076	0.4294	0.7189	0.033*
O16	0.33648 (14)	0.48724 (6)	1.34167 (14)	0.0397 (3)
N17	0.34715 (16)	0.53956 (6)	0.64489 (16)	0.0325 (4)
H17	0.3530	0.5103	0.5792	0.039*
C18	0.36701 (17)	0.60072 (8)	0.60389 (18)	0.0279 (4)
C19	0.29900 (17)	0.64925 (8)	0.65027 (18)	0.0269 (4)
H19	0.2392	0.6415	0.7131	0.032*
C20	0.31876 (17)	0.70897 (8)	0.60449 (18)	0.0267 (4)
C21	0.40671 (18)	0.72084 (8)	0.5136 (2)	0.0312 (4)
H21	0.4230	0.7619	0.4863	0.037*
C22	0.47030 (18)	0.67210 (9)	0.4632 (2)	0.0344 (4)
H22	0.5280	0.6798	0.3976	0.041*
C23	0.45104 (18)	0.61242 (8)	0.5069 (2)	0.0321 (4)
H23	0.4950	0.5794	0.4709	0.039*
N24	0.24633 (15)	0.75736 (6)	0.65095 (15)	0.0291 (3)
H24	0.2255	0.7522	0.7444	0.035*
C25	0.18520 (17)	0.80036 (8)	0.55246 (18)	0.0262 (4)
O26	0.18260 (14)	0.79914 (6)	0.41345 (14)	0.0400 (3)
C27	0.12282 (16)	0.85057 (8)	0.61918 (19)	0.0265 (4)
C28	0.04935 (19)	0.89762 (9)	0.5342 (2)	0.0392 (5)
H28	0.0280	0.9008	0.4250	0.047*
C29	0.01532 (18)	0.93667 (9)	0.6332 (2)	0.0373 (4)
H29	−0.0351	0.9724	0.6059	0.045*
O30	0.06443 (17)	0.91741 (7)	0.78210 (18)	0.0579 (4)
C31	0.1293 (2)	0.86527 (9)	0.7692 (2)	0.0451 (5)
H31	0.1737	0.8419	0.8540	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0327 (9)	0.0268 (9)	0.0223 (8)	0.0032 (7)	0.0090 (7)	0.0015 (7)
C2	0.0391 (10)	0.0206 (8)	0.0256 (8)	−0.0007 (7)	0.0085 (7)	0.0008 (7)
C3	0.0372 (10)	0.0252 (9)	0.0212 (8)	0.0037 (7)	0.0066 (7)	−0.0032 (7)
C4	0.0328 (9)	0.0227 (8)	0.0222 (8)	0.0043 (7)	0.0087 (7)	0.0015 (6)
C5	0.0394 (10)	0.0263 (9)	0.0238 (8)	0.0076 (8)	0.0103 (7)	0.0019 (7)
C6	0.0350 (10)	0.0349 (10)	0.0222 (8)	0.0031 (8)	0.0062 (7)	0.0055 (7)
C7	0.0417 (11)	0.0512 (12)	0.0266 (9)	0.0012 (9)	0.0099 (8)	0.0027 (8)
C8	0.0502 (13)	0.0741 (17)	0.0365 (11)	−0.0102 (12)	0.0191 (10)	0.0075 (11)
C9	0.0576 (14)	0.0616 (15)	0.0399 (12)	−0.0216 (12)	0.0118 (10)	0.0123 (11)
C10	0.0523 (13)	0.0376 (11)	0.0346 (10)	−0.0071 (9)	0.0056 (9)	0.0092 (8)
C11	0.0367 (10)	0.0314 (10)	0.0277 (9)	0.0010 (8)	0.0042 (8)	0.0079 (7)
C12	0.0489 (12)	0.0223 (9)	0.0389 (10)	0.0044 (8)	0.0146 (9)	0.0030 (8)
C13	0.0557 (12)	0.0220 (9)	0.0299 (9)	−0.0011 (8)	0.0186 (9)	−0.0022 (7)
C14	0.0319 (9)	0.0230 (8)	0.0274 (9)	0.0016 (7)	0.0099 (7)	0.0002 (7)
C15	0.0372 (10)	0.0232 (9)	0.0227 (8)	0.0004 (7)	0.0095 (7)	−0.0048 (7)
O16	0.0678 (10)	0.0308 (7)	0.0232 (6)	0.0006 (7)	0.0153 (6)	−0.0017 (5)
N17	0.0580 (10)	0.0222 (7)	0.0210 (7)	0.0026 (7)	0.0165 (7)	−0.0009 (6)
C18	0.0394 (10)	0.0263 (9)	0.0184 (8)	0.0003 (8)	0.0072 (7)	0.0013 (7)
C19	0.0374 (10)	0.0285 (9)	0.0161 (7)	−0.0002 (7)	0.0083 (7)	0.0009 (6)
C20	0.0358 (10)	0.0267 (9)	0.0170 (7)	0.0007 (7)	0.0042 (7)	−0.0009 (6)
C21	0.0388 (10)	0.0268 (9)	0.0293 (9)	−0.0033 (8)	0.0097 (8)	0.0021 (7)
C22	0.0375 (10)	0.0358 (10)	0.0337 (10)	0.0002 (8)	0.0163 (8)	0.0032 (8)
C23	0.0400 (10)	0.0297 (9)	0.0294 (9)	0.0051 (8)	0.0137 (8)	−0.0007 (7)
N24	0.0469 (9)	0.0267 (8)	0.0162 (7)	0.0040 (7)	0.0123 (6)	0.0019 (6)
C25	0.0347 (9)	0.0259 (9)	0.0191 (8)	−0.0048 (7)	0.0083 (7)	0.0001 (7)
O26	0.0628 (9)	0.0406 (8)	0.0188 (6)	0.0125 (7)	0.0136 (6)	0.0047 (5)
C27	0.0316 (9)	0.0249 (9)	0.0236 (8)	−0.0032 (7)	0.0070 (7)	0.0018 (7)
C28	0.0436 (11)	0.0396 (11)	0.0331 (10)	0.0046 (9)	0.0046 (9)	0.0084 (8)
C29	0.0349 (10)	0.0269 (10)	0.0503 (12)	0.0082 (8)	0.0093 (9)	0.0054 (8)
O30	0.0789 (12)	0.0513 (10)	0.0456 (9)	0.0208 (9)	0.0179 (8)	−0.0055 (7)
C31	0.0696 (15)	0.0386 (11)	0.0267 (10)	0.0212 (11)	0.0087 (9)	−0.0009 (8)

Geometric parameters (Å, º) top

C1—N17	1.384 (2)	C14—C15	1.391 (2)
C1—C15	1.395 (2)	C15—H15	0.9500
C1—C2	1.401 (2)	N17—C18	1.407 (2)
C2—C3	1.372 (2)	N17—H17	0.8739
C2—H2	0.9500	C18—C19	1.394 (2)
C3—C4	1.405 (2)	C18—C23	1.395 (2)
C3—H3	0.9500	C19—C20	1.390 (2)
C4—C14	1.415 (2)	C19—H19	0.9500
C4—C5	1.487 (2)	C20—C21	1.389 (2)
C5—O16	1.233 (2)	C20—N24	1.421 (2)
C5—C6	1.495 (3)	C21—C22	1.385 (3)
C6—C7	1.398 (3)	C21—H21	0.9500
C6—C11	1.399 (3)	C22—C23	1.382 (3)
C7—C8	1.382 (3)	C22—H22	0.9500
C7—H7	0.9500	C23—H23	0.9500
C8—C9	1.377 (3)	N24—C25	1.354 (2)
C8—H8	0.9500	N24—H24	0.9089
C9—C10	1.381 (3)	C25—O26	1.2274 (19)
C9—H9	0.9500	C25—C27	1.469 (2)
C10—C11	1.395 (3)	C27—C31	1.356 (2)
C10—H10	0.9500	C27—C28	1.412 (2)
C11—C12	1.501 (3)	C28—C29	1.326 (3)
C12—C13	1.525 (3)	C28—H28	0.9500
C12—H12A	0.9900	C29—O30	1.382 (2)
C12—H12B	0.9900	C29—H29	0.9500
C13—C14	1.512 (2)	O30—C31	1.349 (2)
C13—H13A	0.9900	C31—H31	0.9500
C13—H13B	0.9900

N17—C1—C15	118.86 (15)	C15—C14—C13	115.93 (15)
N17—C1—C2	123.30 (16)	C4—C14—C13	125.51 (15)
C15—C1—C2	117.79 (15)	C14—C15—C1	123.27 (15)
C3—C2—C1	119.60 (16)	C14—C15—H15	118.4
C3—C2—H2	120.2	C1—C15—H15	118.4
C1—C2—H2	120.2	C1—N17—C18	127.17 (14)
C2—C3—C4	123.15 (16)	C1—N17—H17	113.4
C2—C3—H3	118.4	C18—N17—H17	118.7
C4—C3—H3	118.4	C19—C18—C23	119.41 (16)
C3—C4—C14	117.59 (15)	C19—C18—N17	121.48 (15)
C3—C4—C5	114.38 (14)	C23—C18—N17	118.99 (15)
C14—C4—C5	127.98 (15)	C20—C19—C18	119.97 (16)
O16—C5—C4	119.09 (16)	C20—C19—H19	120.0
O16—C5—C6	116.80 (15)	C18—C19—H19	120.0
C4—C5—C6	123.85 (15)	C21—C20—C19	120.47 (16)
C7—C6—C11	119.61 (17)	C21—C20—N24	120.79 (15)
C7—C6—C5	116.52 (17)	C19—C20—N24	118.74 (15)
C11—C6—C5	123.83 (16)	C22—C21—C20	119.14 (16)
C8—C7—C6	120.6 (2)	C22—C21—H21	120.4
C8—C7—H7	119.7	C20—C21—H21	120.4
C6—C7—H7	119.7	C23—C22—C21	121.02 (17)
C9—C8—C7	119.8 (2)	C23—C22—H22	119.5
C9—C8—H8	120.1	C21—C22—H22	119.5
C7—C8—H8	120.1	C22—C23—C18	119.89 (16)
C8—C9—C10	120.2 (2)	C22—C23—H23	120.1
C8—C9—H9	119.9	C18—C23—H23	120.1
C10—C9—H9	119.9	C25—N24—C20	123.20 (14)
C9—C10—C11	121.1 (2)	C25—N24—H24	119.6
C9—C10—H10	119.5	C20—N24—H24	115.3
C11—C10—H10	119.5	O26—C25—N24	122.68 (16)
C10—C11—C6	118.66 (18)	O26—C25—C27	120.20 (16)
C10—C11—C12	120.43 (17)	N24—C25—C27	117.10 (14)
C6—C11—C12	120.91 (16)	C31—C27—C28	105.22 (16)
C11—C12—C13	112.11 (16)	C31—C27—C25	129.44 (16)
C11—C12—H12A	109.2	C28—C27—C25	125.17 (16)
C13—C12—H12A	109.2	C29—C28—C27	108.14 (17)
C11—C12—H12B	109.2	C29—C28—H28	125.9
C13—C12—H12B	109.2	C27—C28—H28	125.9
H12A—C12—H12B	107.9	C28—C29—O30	109.57 (17)
C14—C13—C12	116.24 (16)	C28—C29—H29	125.2
C14—C13—H13A	108.2	O30—C29—H29	125.2
C12—C13—H13A	108.2	C31—O30—C29	106.05 (15)
C14—C13—H13B	108.2	O30—C31—C27	111.01 (17)
C12—C13—H13B	108.2	O30—C31—H31	124.5
H13A—C13—H13B	107.4	C27—C31—H31	124.5
C15—C14—C4	118.53 (15)

N17—C1—C2—C3	−178.94 (17)	C4—C14—C15—C1	0.3 (3)
C15—C1—C2—C3	−1.7 (3)	C13—C14—C15—C1	−177.81 (17)
C1—C2—C3—C4	−0.7 (3)	N17—C1—C15—C14	179.27 (17)
C2—C3—C4—C14	2.9 (3)	C2—C1—C15—C14	1.9 (3)
C2—C3—C4—C5	−174.59 (17)	C15—C1—N17—C18	179.19 (17)
C3—C4—C5—O16	−14.7 (2)	C2—C1—N17—C18	−3.6 (3)
C14—C4—C5—O16	168.12 (18)	C1—N17—C18—C19	−45.9 (3)
C3—C4—C5—C6	159.21 (16)	C1—N17—C18—C23	138.03 (19)
C14—C4—C5—C6	−18.0 (3)	C23—C18—C19—C20	−2.4 (3)
O16—C5—C6—C7	35.6 (2)	N17—C18—C19—C20	−178.41 (16)
C4—C5—C6—C7	−138.42 (18)	C18—C19—C20—C21	−0.5 (3)
O16—C5—C6—C11	−142.16 (18)	C18—C19—C20—N24	178.77 (15)
C4—C5—C6—C11	43.8 (3)	C19—C20—C21—C22	2.9 (3)
C11—C6—C7—C8	−1.1 (3)	N24—C20—C21—C22	−176.33 (16)
C5—C6—C7—C8	−178.99 (18)	C20—C21—C22—C23	−2.5 (3)
C6—C7—C8—C9	0.9 (3)	C21—C22—C23—C18	−0.4 (3)
C7—C8—C9—C10	0.0 (3)	C19—C18—C23—C22	2.8 (3)
C8—C9—C10—C11	−0.7 (3)	N17—C18—C23—C22	178.94 (17)
C9—C10—C11—C6	0.5 (3)	C21—C20—N24—C25	47.7 (2)
C9—C10—C11—C12	−179.72 (19)	C19—C20—N24—C25	−131.59 (18)
C7—C6—C11—C10	0.4 (3)	C20—N24—C25—O26	3.6 (3)
C5—C6—C11—C10	178.11 (17)	C20—N24—C25—C27	−175.05 (15)
C7—C6—C11—C12	−179.36 (17)	O26—C25—C27—C31	−169.7 (2)
C5—C6—C11—C12	−1.7 (3)	N24—C25—C27—C31	9.0 (3)
C10—C11—C12—C13	114.25 (19)	O26—C25—C27—C28	4.7 (3)
C6—C11—C12—C13	−66.0 (2)	N24—C25—C27—C28	−176.57 (17)
C11—C12—C13—C14	75.8 (2)	C31—C27—C28—C29	−0.6 (2)
C3—C4—C14—C15	−2.7 (2)	C25—C27—C28—C29	−176.09 (17)
C5—C4—C14—C15	174.47 (17)	C27—C28—C29—O30	0.4 (2)
C3—C4—C14—C13	175.28 (17)	C28—C29—O30—C31	0.0 (2)
C5—C4—C14—C13	−7.6 (3)	C29—O30—C31—C27	−0.3 (3)
C12—C13—C14—C15	153.30 (17)	C28—C27—C31—O30	0.6 (2)
C12—C13—C14—C4	−24.7 (3)	C25—C27—C31—O30	175.83 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O16ⁱ	0.87	2.14	2.900 (2)	146
N24—H24···O26ⁱⁱ	0.91	2.00	2.839 (2)	153
C21—H21···O21	0.95	2.66	2.937 (2)	97

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₃
M_r	408.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.7691 (7), 21.746 (1), 8.8666 (6)
β (°)	101.934 (2)
V (Å³)	2031.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22214, 4856, 3347
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.115, 0.99
No. of reflections	4856
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), 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
N17—H17···O16ⁱ	0.87	2.14	2.900 (2)	146
N24—H24···O26ⁱⁱ	0.91	2.00	2.839 (2)	153
C21—H21···O21	0.95	2.66	2.937 (2)	97

Symmetry codes: (i) x, y, z−1; (ii) x, −y+3/2, 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
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grasa, G. A., Viciu, M. S., Huang, J. & Nolan, S. P. (2001). J. Org. Chem. 66, 7729–7737. Web of Science CrossRef PubMed CAS Google Scholar
Jensen, T. A., Liang, X., Tanner, D. & Skjaerbaek, N. J. (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 66| Part 5| May 2010| Page o1100

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[3-(5-Oxo-10,11-di­hydro-5H-dibenzo[a,d]cyclo­hepten-2-ylamino)phen­yl]furan-3-carboxamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-[3-(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-ylamino)phenyl]furan-3-carboxamide