N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo­hepten-2-yl)amino]­phen­yl}benzamide

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

doi:10.1107/S1600536810024256

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1867

doi:10.1107/S1600536810024256

Open

access

N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yl)amino]phenyl}benzamide

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, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 10 June 2010; accepted 22 June 2010; online 30 June 2010)

In the title compound, C₂₉H₂₄N₂O₂, 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 molecules into chains along the a axis. Further N—H⋯·O interactions 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_r = 432.50
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.00
5388 reflections
301 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯O16ⁱ	0.88 (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) x+1, y, z; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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: 10.1107/S1600536810024256/zl2285sup1.cif

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

checkCIF report

Comment top

Recently we designed and synthesized a series of p38 MAP kinase inhibitors based on dibenzosuberones (Laufer et al. 2006). The title compound was synthesized in the course of our ongoing studies on dibenzo[a,d]cycloheptan-5-ones as potent p38 mitogen-activated protein (MAP) kinase inhibitors.

The structure of the title compound, at 173 (2) K has orthorhombic 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 = 32.27 (8)°. In the crystal structure N17—H17···O16 (2.89 (2) Å) forms a chain parallel to the a-axis and N25—H25···O27 (2.86 (2) Å) links two by the c-glide plane related chains together (Fig.2).

Related literature top

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 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]cyclohepten-5-one, 470 mg (2.1 mmol) N-(5-amino-2-methylphenyl)benzamide, 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 3 h at 264 K (90 °C) under an atmosphere of argon. The mixture was diluted with water 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 7 + 3) (yield: 16.3%). Crystals of the title compound were obtained by slow evaporation of a acetone / ethyl acetate / diethyl ether solution at room temperature. IR (ATR): 3312, 1648, 1575, 1544, 1511, 1292, 1275, 1263, 1109, 763, 701, 689cm^-1. ¹H-NMR (DMSO-d6) d in ppm: 2.21 (s, 3H), 3.07 (s, 4H), 6.87-7.04 (m, 3H), 7.20-7.59 (m, 8H), 7.84 (d, J=7.8 Hz, 1H), 7.96-8.01 (m, 3H), 8.80 (s, 1H, NH), 9.83 (s, 1H, NH). ¹³C-NMR (DMSO-d6) d in ppm: 17.7, 34.4, 36.2, 112.9, 114.3, 118.0, 118.3, 126.8, 127.3, 127.5, 128.0 (x2), 128.8 (x2), 129.0, 130.5, 131.3, 131.9, 132.2, 133.8, 135.0, 137.3, 139.3, 139.4, 142.0, 145.8, 149.0, 165.7, 191.0. HRMS-ESI, m/z (C₂₉H₂₄N₂O₂): calcd, 432.1838 [M+H]+; found, 432.1860.

¹H NMR (200 MHz) and ¹³C NMR (50 MHz) were recorded on a Bruker Advance 200. IR data were determined on a Perkin-Elmer Spectrum One spectrometer (ATR technique). HRMS (EI) (electron impact – high resolution mass spectroscopy) data were obtained from the department for mass spectrometry, Institute of Organic chemistry, Eberhard-Karls-University Tübingen.

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 the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the packing diagram illustrating the hydrogen bonds. View along the b-axis.

N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H- dibenzo[a,d]cyclohepten-2-yl)amino]phenyl}benzamide top

Crystal data top

C₂₉H₂₄N₂O₂	F(000) = 1824
M_r = 432.50	D_x = 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

Data collection top

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

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)] = 0.044	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(F_o²) + (0.0522P)² + 1.6792P] where P = (F_o² + 2F_c²)/3
5388 reflections	(Δ/σ)_max = 0.002
301 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₉H₂₄N₂O₂	V = 4486.4 (5) Å³
M_r = 432.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.5878 (6) Å	µ = 0.08 mm⁻¹
b = 17.0342 (12) Å	T = 173 K
c = 30.669 (2) Å	0.50 × 0.13 × 0.06 mm

Data collection top

Bruker SMART APEXII diffractometer	3740 reflections with I > 2σ(I)
54075 measured reflections	R_int = 0.069
5388 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.24 e Å⁻³
5388 reflections	Δρ_min = −0.19 e Å⁻³
301 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	0.56067 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₄N₂O₂
M_r	432.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	8.5878 (6), 17.0342 (12), 30.669 (2)
V (Å³)	4486.4 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.13 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	54075, 5388, 3740
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.00
No. of reflections	5388
No. of parameters	301
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

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	0.880 (19)	2.040 (19)	2.8934 (18)	163.08 (17)
N25—H25···O27ⁱⁱ	0.905 (18)	2.005 (17)	2.8566 (17)	156.3 (2)

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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1867

doi:10.1107/S1600536810024256

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N-{2-Methyl-5-[(5-oxo-10,11-di­hydro-5H-dibenzo[a,d]cyclo­hepten-2-yl)amino]­phen­yl}benzamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-yl)amino]phenyl}benzamide