N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo-hepten-2-yl)amino]-phen-yl}benzamide.

In the title compound, C(29)H(24)N(2)O(2), the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 32.27 (8)°. In the crystal N-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis. Further N-H⋯·O inter-actions link the chains.

Related literature

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

Experimental

Crystal data

C29H24N2O2

M = 432.50

Orthorhombic,

a = 8.5878 (6) Å

b = 17.0342 (12) Å

c = 30.669 (2) Å

V = 4486.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.50 × 0.13 × 0.06 mm

Data collection

Bruker SMART APEXIIdiffractometer

54075 measured reflections

5388 independent reflections

3740 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.00

5388 reflections

301 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.19 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/S1600536810024256/zl2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024256/zl2285Isup2.hkl

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

C29H24N2O2	F(000) = 1824
Mr = 432.50	Dx = 1.281 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6479 reflections
a = 8.5878 (6) Å	θ = 2.4–24.1°
b = 17.0342 (12) Å	µ = 0.08 mm−1
c = 30.669 (2) Å	T = 173 K
V = 4486.4 (5) Å3	Plate, yellow
Z = 8	0.50 × 0.13 × 0.06 mm

Bruker SMART APEXII diffractometer	3740 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.069
graphite	θmax = 27.9°, θmin = 2.4°
CCD scan	h = −11→11
54075 measured reflections	k = −21→22
5388 independent reflections	l = −40→39

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0522P)2 + 1.6792P] where P = (Fo2 + 2Fc2)/3
5388 reflections	(Δ/σ)max = 0.002
301 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.19 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	0.56067 (17)	0.43978 (9)	0.43200 (5)	0.0264 (3)
C2	0.42391 (17)	0.45759 (10)	0.40902 (5)	0.0303 (4)
H2	0.4294	0.4810	0.3810	0.036*
C3	0.28200 (17)	0.44081 (10)	0.42747 (5)	0.0294 (3)
H3	0.1905	0.4539	0.4117	0.035*
C4	0.26547 (17)	0.40522 (9)	0.46867 (5)	0.0266 (3)
C5	0.10305 (18)	0.39527 (9)	0.48427 (5)	0.0291 (3)
C6	0.05457 (17)	0.35895 (9)	0.52689 (5)	0.0278 (3)
C7	−0.08844 (18)	0.38403 (10)	0.54369 (5)	0.0327 (4)
H7	−0.1429	0.4252	0.5294	0.039*
C8	−0.1525 (2)	0.35043 (11)	0.58062 (5)	0.0382 (4)
H8	−0.2491	0.3689	0.5917	0.046*
C9	−0.0751 (2)	0.28965 (11)	0.60145 (6)	0.0416 (4)
H9	−0.1197	0.2652	0.6263	0.050*
C10	0.0673 (2)	0.26490 (10)	0.58569 (6)	0.0375 (4)
H10	0.1208	0.2239	0.6004	0.045*
C11	0.13471 (18)	0.29860 (9)	0.54876 (5)	0.0295 (3)
C12	0.29383 (19)	0.27248 (9)	0.53467 (6)	0.0332 (4)
H12A	0.2876	0.2489	0.5052	0.040*
H12B	0.3329	0.2319	0.5550	0.040*
C13	0.40667 (18)	0.34182 (10)	0.53394 (5)	0.0308 (4)
H13A	0.3797	0.3783	0.5579	0.037*
H13B	0.5136	0.3223	0.5393	0.037*
C14	0.40373 (17)	0.38601 (9)	0.49132 (5)	0.0249 (3)
C15	0.54564 (17)	0.40451 (9)	0.47287 (5)	0.0260 (3)
H15	0.6376	0.3927	0.4888	0.031*
O16	−0.00360 (13)	0.42043 (8)	0.46106 (4)	0.0426 (3)
N17	0.70774 (15)	0.45536 (8)	0.41644 (4)	0.0314 (3)
H17	0.7877 (18)	0.45103 (13)	0.4342 (4)	0.038*
C18	0.74679 (17)	0.47550 (9)	0.37302 (5)	0.0272 (3)
C19	0.68395 (17)	0.43432 (9)	0.33809 (5)	0.0266 (3)
H19	0.6149	0.3917	0.3433	0.032*
C20	0.72163 (16)	0.45516 (9)	0.29563 (5)	0.0254 (3)
C21	0.82292 (18)	0.51809 (9)	0.28699 (5)	0.0297 (3)
C22	0.89126 (19)	0.55434 (10)	0.32282 (6)	0.0350 (4)
H22	0.9662	0.5944	0.3179	0.042*
C23	0.85449 (18)	0.53435 (10)	0.36533 (5)	0.0332 (4)
H23	0.9027	0.5608	0.3890	0.040*
C24	0.8502 (2)	0.54853 (11)	0.24131 (6)	0.0401 (4)
H24A	0.9054	0.5988	0.2427	0.060*
H24B	0.7499	0.5559	0.2266	0.060*
H24C	0.9130	0.5106	0.2249	0.060*
N25	0.66532 (14)	0.41082 (8)	0.25969 (4)	0.0283 (3)
H25	0.7321 (14)	0.3984 (3)	0.2380 (5)	0.034*
C26	0.53364 (17)	0.36762 (9)	0.25892 (5)	0.0277 (3)
O27	0.43664 (12)	0.36770 (7)	0.28857 (4)	0.0352 (3)
C28	0.51003 (18)	0.31897 (10)	0.21871 (5)	0.0301 (4)
C29	0.4196 (2)	0.25209 (11)	0.22279 (6)	0.0466 (5)
H29	0.3747	0.2390	0.2501	0.056*
C30	0.3948 (3)	0.20449 (13)	0.18704 (7)	0.0627 (6)
H30	0.3353	0.1578	0.1901	0.075*
C31	0.4558 (3)	0.22431 (13)	0.14716 (7)	0.0577 (6)
H31	0.4380	0.1913	0.1227	0.069*
C32	0.5426 (2)	0.29157 (13)	0.14238 (6)	0.0496 (5)
H32	0.5829	0.3055	0.1146	0.060*
C33	0.5709 (2)	0.33890 (12)	0.17818 (6)	0.0385 (4)
H33	0.6321	0.3850	0.1751	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0229 (7)	0.0303 (8)	0.0260 (8)	0.0015 (6)	−0.0023 (6)	−0.0063 (6)
C2	0.0257 (8)	0.0420 (9)	0.0232 (8)	0.0040 (7)	−0.0026 (6)	0.0007 (7)
C3	0.0229 (8)	0.0403 (9)	0.0248 (8)	0.0057 (6)	−0.0060 (6)	−0.0025 (7)
C4	0.0232 (7)	0.0314 (8)	0.0252 (8)	0.0016 (6)	−0.0037 (6)	−0.0038 (6)
C5	0.0239 (8)	0.0335 (8)	0.0300 (8)	0.0000 (6)	−0.0058 (6)	−0.0047 (7)
C6	0.0235 (7)	0.0324 (8)	0.0274 (8)	−0.0059 (6)	−0.0030 (6)	−0.0078 (6)
C7	0.0257 (8)	0.0392 (9)	0.0330 (9)	−0.0041 (7)	−0.0041 (7)	−0.0088 (7)
C8	0.0281 (8)	0.0500 (11)	0.0364 (10)	−0.0085 (8)	0.0030 (7)	−0.0108 (8)
C9	0.0409 (10)	0.0458 (11)	0.0380 (10)	−0.0154 (8)	0.0058 (8)	−0.0030 (8)
C10	0.0412 (10)	0.0314 (9)	0.0397 (10)	−0.0072 (7)	0.0003 (8)	−0.0008 (7)
C11	0.0302 (8)	0.0267 (8)	0.0315 (8)	−0.0049 (6)	−0.0016 (7)	−0.0057 (6)
C12	0.0348 (9)	0.0298 (8)	0.0350 (9)	0.0036 (7)	−0.0006 (7)	0.0012 (7)
C13	0.0258 (8)	0.0375 (9)	0.0292 (8)	0.0037 (7)	−0.0034 (7)	0.0034 (7)
C14	0.0249 (7)	0.0251 (7)	0.0248 (8)	0.0020 (6)	−0.0034 (6)	−0.0048 (6)
C15	0.0224 (7)	0.0307 (8)	0.0249 (8)	0.0038 (6)	−0.0073 (6)	−0.0044 (6)
O16	0.0218 (6)	0.0675 (9)	0.0384 (7)	0.0022 (6)	−0.0066 (5)	0.0083 (6)
N17	0.0207 (6)	0.0500 (9)	0.0235 (7)	0.0001 (6)	−0.0050 (5)	−0.0013 (6)
C18	0.0203 (7)	0.0350 (8)	0.0263 (8)	0.0023 (6)	−0.0020 (6)	−0.0018 (6)
C19	0.0193 (7)	0.0315 (8)	0.0292 (8)	−0.0014 (6)	−0.0010 (6)	−0.0007 (6)
C20	0.0183 (7)	0.0313 (8)	0.0266 (8)	0.0007 (6)	−0.0017 (6)	−0.0035 (6)
C21	0.0250 (8)	0.0324 (8)	0.0317 (8)	−0.0010 (6)	0.0027 (7)	0.0006 (7)
C22	0.0298 (9)	0.0342 (9)	0.0411 (10)	−0.0095 (7)	0.0014 (7)	−0.0031 (7)
C23	0.0272 (8)	0.0388 (9)	0.0336 (9)	−0.0039 (7)	−0.0041 (7)	−0.0094 (7)
C24	0.0409 (10)	0.0405 (10)	0.0390 (10)	−0.0062 (8)	0.0048 (8)	0.0061 (8)
N25	0.0202 (6)	0.0398 (8)	0.0248 (7)	−0.0032 (5)	0.0022 (5)	−0.0048 (6)
C26	0.0211 (7)	0.0364 (9)	0.0255 (8)	−0.0003 (6)	−0.0022 (6)	0.0008 (6)
O27	0.0225 (5)	0.0576 (8)	0.0253 (6)	−0.0072 (5)	0.0001 (5)	−0.0021 (5)
C28	0.0229 (7)	0.0383 (9)	0.0291 (8)	0.0008 (7)	−0.0061 (6)	−0.0029 (7)
C29	0.0565 (12)	0.0457 (11)	0.0377 (10)	−0.0158 (9)	−0.0097 (9)	0.0012 (8)
C30	0.0861 (17)	0.0457 (12)	0.0562 (14)	−0.0244 (12)	−0.0216 (12)	−0.0030 (10)
C31	0.0736 (15)	0.0564 (13)	0.0431 (12)	0.0011 (11)	−0.0194 (11)	−0.0191 (10)
C32	0.0470 (11)	0.0682 (14)	0.0337 (10)	0.0006 (10)	−0.0015 (9)	−0.0120 (9)
C33	0.0311 (9)	0.0524 (11)	0.0320 (9)	−0.0058 (8)	−0.0004 (7)	−0.0061 (8)

C1—N17	1.3760 (19)	N17—H17	0.880 (19)
C1—C15	1.396 (2)	C18—C23	1.384 (2)
C1—C2	1.403 (2)	C18—C19	1.390 (2)
C2—C3	1.374 (2)	C19—C20	1.388 (2)
C2—H2	0.9500	C19—H19	0.9500
C3—C4	1.409 (2)	C20—C21	1.406 (2)
C3—H3	0.9500	C20—N25	1.4210 (19)
C4—C14	1.414 (2)	C21—C22	1.390 (2)
C4—C5	1.484 (2)	C21—C24	1.512 (2)
C5—O16	1.2366 (19)	C22—C23	1.384 (2)
C5—C6	1.505 (2)	C22—H22	0.9500
C6—C7	1.399 (2)	C23—H23	0.9500
C6—C11	1.407 (2)	C24—H24A	0.9800
C7—C8	1.383 (2)	C24—H24B	0.9800
C7—H7	0.9500	C24—H24C	0.9800
C8—C9	1.386 (3)	N25—C26	1.3494 (19)
C8—H8	0.9500	N25—H25	0.905 (18)
C9—C10	1.381 (3)	C26—O27	1.2334 (18)
C9—H9	0.9500	C26—C28	1.499 (2)
C10—C11	1.395 (2)	C28—C29	1.384 (2)
C10—H10	0.9500	C28—C33	1.391 (2)
C11—C12	1.501 (2)	C29—C30	1.380 (3)
C12—C13	1.528 (2)	C29—H29	0.9500
C12—H12A	0.9900	C30—C31	1.373 (3)
C12—H12B	0.9900	C30—H30	0.9500
C13—C14	1.509 (2)	C31—C32	1.374 (3)
C13—H13A	0.9900	C31—H31	0.9500
C13—H13B	0.9900	C32—C33	1.384 (2)
C14—C15	1.380 (2)	C32—H32	0.9500
C15—H15	0.9500	C33—H33	0.9500
N17—C18	1.415 (2)
N17—C1—C15	118.63 (13)	C1—N17—C18	126.19 (13)
N17—C1—C2	123.55 (14)	C1—N17—H17	118.98 (8)
C15—C1—C2	117.82 (14)	C18—N17—H17	114.78 (8)
C3—C2—C1	119.41 (15)	C23—C18—C19	119.58 (14)
C3—C2—H2	120.3	C23—C18—N17	119.62 (14)
C1—C2—H2	120.3	C19—C18—N17	120.73 (14)
C2—C3—C4	123.25 (14)	C20—C19—C18	120.25 (14)
C2—C3—H3	118.4	C20—C19—H19	119.9
C4—C3—H3	118.4	C18—C19—H19	119.9
C3—C4—C14	117.11 (14)	C19—C20—C21	121.08 (14)
C3—C4—C5	115.65 (13)	C19—C20—N25	120.82 (14)
C14—C4—C5	127.18 (14)	C21—C20—N25	118.02 (13)
O16—C5—C4	118.09 (14)	C22—C21—C20	116.81 (14)
O16—C5—C6	115.95 (14)	C22—C21—C24	120.97 (15)
C4—C5—C6	125.93 (13)	C20—C21—C24	122.13 (14)
C7—C6—C11	118.48 (15)	C23—C22—C21	122.61 (15)
C7—C6—C5	115.94 (14)	C23—C22—H22	118.7
C11—C6—C5	125.38 (14)	C21—C22—H22	118.7
C8—C7—C6	121.63 (16)	C22—C23—C18	119.42 (15)
C8—C7—H7	119.2	C22—C23—H23	120.3
C6—C7—H7	119.2	C18—C23—H23	120.3
C7—C8—C9	119.75 (16)	C21—C24—H24A	109.5
C7—C8—H8	120.1	C21—C24—H24B	109.5
C9—C8—H8	120.1	H24A—C24—H24B	109.5
C10—C9—C8	119.40 (17)	C21—C24—H24C	109.5
C10—C9—H9	120.3	H24A—C24—H24C	109.5
C8—C9—H9	120.3	H24B—C24—H24C	109.5
C9—C10—C11	121.72 (17)	C26—N25—C20	126.07 (13)
C9—C10—H10	119.1	C26—N25—H25	113.04 (9)
C11—C10—H10	119.1	C20—N25—H25	118.67 (8)
C10—C11—C6	118.99 (15)	O27—C26—N25	123.53 (14)
C10—C11—C12	119.30 (15)	O27—C26—C28	121.05 (14)
C6—C11—C12	121.65 (14)	N25—C26—C28	115.42 (13)
C11—C12—C13	110.64 (13)	C29—C28—C33	119.51 (16)
C11—C12—H12A	109.5	C29—C28—C26	117.15 (15)
C13—C12—H12A	109.5	C33—C28—C26	123.32 (15)
C11—C12—H12B	109.5	C30—C29—C28	119.88 (19)
C13—C12—H12B	109.5	C30—C29—H29	120.1
H12A—C12—H12B	108.1	C28—C29—H29	120.1
C14—C13—C12	112.82 (13)	C31—C30—C29	120.3 (2)
C14—C13—H13A	109.0	C31—C30—H30	119.9
C12—C13—H13A	109.0	C29—C30—H30	119.9
C14—C13—H13B	109.0	C30—C31—C32	120.45 (18)
C12—C13—H13B	109.0	C30—C31—H31	119.8
H13A—C13—H13B	107.8	C32—C31—H31	119.8
C15—C14—C4	119.15 (14)	C31—C32—C33	119.76 (19)
C15—C14—C13	117.03 (13)	C31—C32—H32	120.1
C4—C14—C13	123.73 (14)	C33—C32—H32	120.1
C14—C15—C1	123.23 (14)	C32—C33—C28	120.05 (17)
C14—C15—H15	118.4	C32—C33—H33	120.0
C1—C15—H15	118.4	C28—C33—H33	120.0
N17—C1—C2—C3	−179.11 (15)	N17—C1—C15—C14	−179.60 (14)
C15—C1—C2—C3	0.7 (2)	C2—C1—C15—C14	0.5 (2)
C1—C2—C3—C4	−0.8 (3)	C15—C1—N17—C18	166.23 (15)
C2—C3—C4—C14	−0.4 (2)	C2—C1—N17—C18	−13.9 (3)
C2—C3—C4—C5	177.03 (15)	C1—N17—C18—C23	137.86 (17)
C3—C4—C5—O16	−2.0 (2)	C1—N17—C18—C19	−45.3 (2)
C14—C4—C5—O16	175.13 (15)	C23—C18—C19—C20	−3.9 (2)
C3—C4—C5—C6	179.85 (14)	N17—C18—C19—C20	179.24 (14)
C14—C4—C5—C6	−3.0 (3)	C18—C19—C20—C21	−0.3 (2)
O16—C5—C6—C7	−24.6 (2)	C18—C19—C20—N25	176.39 (14)
C4—C5—C6—C7	153.62 (15)	C19—C20—C21—C22	4.4 (2)
O16—C5—C6—C11	150.24 (16)	N25—C20—C21—C22	−172.33 (14)
C4—C5—C6—C11	−31.6 (2)	C19—C20—C21—C24	−172.18 (15)
C11—C6—C7—C8	−0.7 (2)	N25—C20—C21—C24	11.1 (2)
C5—C6—C7—C8	174.43 (14)	C20—C21—C22—C23	−4.7 (2)
C6—C7—C8—C9	−0.9 (2)	C24—C21—C22—C23	171.97 (16)
C7—C8—C9—C10	1.8 (3)	C21—C22—C23—C18	0.7 (3)
C8—C9—C10—C11	−1.1 (3)	C19—C18—C23—C22	3.7 (2)
C9—C10—C11—C6	−0.5 (2)	N17—C18—C23—C22	−179.41 (15)
C9—C10—C11—C12	176.51 (15)	C19—C20—N25—C26	26.7 (2)
C7—C6—C11—C10	1.4 (2)	C21—C20—N25—C26	−156.54 (15)
C5—C6—C11—C10	−173.26 (14)	C20—N25—C26—O27	7.6 (3)
C7—C6—C11—C12	−175.52 (14)	C20—N25—C26—C28	−173.21 (14)
C5—C6—C11—C12	9.8 (2)	O27—C26—C28—C29	−26.9 (2)
C10—C11—C12—C13	−121.01 (16)	N25—C26—C28—C29	153.85 (16)
C6—C11—C12—C13	55.9 (2)	O27—C26—C28—C33	151.57 (17)
C11—C12—C13—C14	−86.65 (17)	N25—C26—C28—C33	−27.7 (2)
C3—C4—C14—C15	1.6 (2)	C33—C28—C29—C30	2.1 (3)
C5—C4—C14—C15	−175.47 (15)	C26—C28—C29—C30	−179.38 (18)
C3—C4—C14—C13	−174.79 (14)	C28—C29—C30—C31	−1.8 (3)
C5—C4—C14—C13	8.1 (2)	C29—C30—C31—C32	0.2 (4)
C12—C13—C14—C15	−133.61 (14)	C30—C31—C32—C33	1.2 (3)
C12—C13—C14—C4	42.9 (2)	C31—C32—C33—C28	−0.9 (3)
C4—C14—C15—C1	−1.8 (2)	C29—C28—C33—C32	−0.7 (3)
C13—C14—C15—C1	174.91 (14)	C26—C28—C33—C32	−179.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···O16i	0.88 (2)	2.04 (2)	2.8934 (18)	163 (1)
N25—H25···O27ii	0.91 (2)	2.01 (2)	2.8566 (17)	156 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯O16i	0.88 (2)	2.04 (2)	2.8934 (18)	163 (1)
N25—H25⋯O27ii	0.91 (2)	2.01 (2)	2.8566 (17)	156 (1)

Symmetry codes: (i) ; (ii) .