N-[3-(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo-hepten-2-ylamino)phen-yl]furan-3-carboxamide.

In the title compound, C(26)H(20)N(2)O(3), the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 54.53 (9)°. The crystal structure displays inter-molecular 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 = 408.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.115

S = 0.99

4856 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.30 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013450/im2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013450/im2187Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C26H20N2O3	F(000) = 856
Mr = 408.44	Dx = 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

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

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(Fo2) + (0.0358P)2 + 1.2737P] where P = (Fo2 + 2Fc2)/3
4856 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .