2,4-Bis(furan-2-yl)-1,5-dimethyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

In the title compound, C18H21NO3, the bicyclic ring system adopts a twin-chair conformation. The two methyl groups attached to the bicycle are in an equatorial orientation for both rings. One of the furan rings is disordered over two orientations with an occupancy ratio of 0.686 (6):0.314 (6). In the crystal, very long N-H⋯O hydrogen bonds connect the mol-ecules into a chain perpendicular to the ac plane.

Related literature

For the synthesis and biological activity of 3-aza­bicyclo­[3.3.1] nonan-9-ones, see: Parthiban et al. (2009 ▶); Hardick et al. (1996 ▶); Jeyaraman & Avila (1981 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H21NO3

M = 299.36

Monoclinic,

a = 21.268 (2) Å

b = 6.7031 (9) Å

c = 22.303 (2) Å

β = 92.776 (6)°

V = 3175.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

11487 measured reflections

2784 independent reflections

2127 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.05

2784 reflections

252 parameters

220 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010180/aa2083sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010180/aa2083Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010180/aa2083Isup3.cml

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

C18H21NO3	F(000) = 1280
Mr = 299.36	Dx = 1.252 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11487 reflections
a = 21.268 (2) Å	θ = 1.8–28.4°
b = 6.7031 (9) Å	µ = 0.09 mm−1
c = 22.303 (2) Å	T = 293 K
β = 92.776 (6)°	Block, brown
V = 3175.7 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	2127 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ω scan	h = −23→25
11487 measured reflections	k = −5→7
2784 independent reflections	l = −22→26

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0637P)2 + 1.7182P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2784 reflections	Δρmax = 0.19 e Å−3
252 parameters	Δρmin = −0.20 e Å−3
220 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (5)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.17290 (7)	0.0845 (3)	0.13064 (7)	0.0446 (4)
H1	0.1765 (10)	0.215 (4)	0.1368 (9)	0.058 (6)*
C2	0.23315 (8)	−0.0076 (3)	0.15048 (8)	0.0391 (4)
H2	0.2398	0.0198	0.1935	0.047*
C3	0.23109 (8)	−0.2391 (3)	0.14260 (8)	0.0403 (4)
C4	0.21984 (10)	−0.3083 (3)	0.07672 (8)	0.0506 (5)
H4A	0.2530	−0.2539	0.0532	0.061*
H4B	0.2233	−0.4526	0.0755	0.061*
C5	0.15671 (10)	−0.2485 (3)	0.04728 (9)	0.0562 (6)
H5A	0.1501	−0.3209	0.0098	0.067*
H5B	0.1573	−0.1072	0.0380	0.067*
C6	0.10205 (10)	−0.2917 (3)	0.08770 (9)	0.0544 (5)
H6A	0.0942	−0.4342	0.0873	0.065*
H6B	0.0646	−0.2267	0.0706	0.065*
C7	0.11233 (9)	−0.2234 (3)	0.15358 (8)	0.0455 (5)
C8	0.17479 (9)	−0.3139 (3)	0.17506 (8)	0.0444 (5)
C9	0.11855 (8)	0.0068 (3)	0.16110 (9)	0.0461 (5)
H9	0.1259	0.0337	0.2041	0.055*
C10	0.29224 (10)	−0.3283 (3)	0.16918 (10)	0.0595 (6)
H10A	0.3007	−0.2761	0.2088	0.089*
H10B	0.3262	−0.2941	0.1443	0.089*
H10C	0.2883	−0.4708	0.1711	0.089*
C11	0.05852 (10)	−0.2986 (4)	0.19039 (11)	0.0701 (7)
H11A	0.0591	−0.4417	0.1914	0.105*
H11B	0.0191	−0.2537	0.1724	0.105*
H11C	0.0635	−0.2476	0.2306	0.105*
C21	0.28552 (8)	0.0899 (3)	0.11924 (8)	0.0418 (4)
C22	0.34330 (9)	0.1509 (3)	0.13830 (10)	0.0559 (5)
H22	0.3611	0.1405	0.1771	0.067*
C23	0.37202 (10)	0.2347 (3)	0.08755 (11)	0.0627 (6)
H23	0.4122	0.2893	0.0869	0.075*
C24	0.33033 (10)	0.2198 (3)	0.04147 (11)	0.0616 (6)
H24	0.3368	0.2637	0.0027	0.074*
O1	0.17859 (7)	−0.4444 (3)	0.21255 (7)	0.0744 (5)
O2	0.27645 (6)	0.1308 (2)	0.05925 (6)	0.0564 (4)
C91	0.0595 (4)	0.114 (2)	0.1410 (2)	0.0532 (11)	0.686 (6)
C92	0.0368 (2)	0.1727 (7)	0.0867 (2)	0.0656 (11)	0.686 (6)
H92	0.0561	0.1616	0.0503	0.079*	0.686 (6)
C93	−0.0247 (4)	0.2576 (19)	0.0973 (3)	0.0883 (17)	0.686 (6)
H93	−0.0535	0.3089	0.0686	0.106*	0.686 (6)
C94	−0.03169 (18)	0.2467 (7)	0.1581 (3)	0.0947 (15)	0.686 (6)
H94	−0.0667	0.2934	0.1772	0.114*	0.686 (6)
O3	0.02057 (15)	0.1562 (6)	0.18791 (19)	0.0811 (11)	0.686 (6)
C91'	0.0638 (9)	0.116 (5)	0.1303 (6)	0.064 (2)	0.314 (6)
C92'	0.0621 (4)	0.1568 (14)	0.0708 (4)	0.0480 (18)	0.314 (6)
H92'	0.0929	0.1318	0.0436	0.058*	0.314 (6)
C93'	0.0022 (4)	0.2467 (14)	0.0597 (5)	0.082 (2)	0.314 (6)
H93'	−0.0137	0.2875	0.0221	0.098*	0.314 (6)
C94'	−0.0289 (9)	0.265 (4)	0.1116 (7)	0.082 (2)	0.314 (6)
H94'	−0.0680	0.3245	0.1158	0.099*	0.314 (6)
O3'	0.0093 (4)	0.1787 (15)	0.1571 (5)	0.094 (2)	0.314 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0369 (8)	0.0346 (9)	0.0622 (10)	0.0025 (7)	0.0027 (7)	0.0001 (7)
C2	0.0388 (9)	0.0386 (10)	0.0398 (9)	0.0028 (8)	0.0001 (7)	−0.0037 (8)
C3	0.0432 (10)	0.0366 (10)	0.0414 (10)	0.0047 (8)	0.0041 (8)	0.0007 (8)
C4	0.0621 (12)	0.0438 (11)	0.0471 (11)	−0.0023 (9)	0.0137 (9)	−0.0073 (9)
C5	0.0743 (14)	0.0538 (13)	0.0401 (10)	−0.0032 (11)	−0.0026 (10)	−0.0072 (9)
C6	0.0555 (12)	0.0462 (12)	0.0607 (13)	−0.0067 (9)	−0.0071 (10)	−0.0054 (9)
C7	0.0431 (10)	0.0451 (11)	0.0486 (11)	−0.0034 (8)	0.0069 (8)	0.0035 (8)
C8	0.0551 (11)	0.0418 (11)	0.0365 (9)	0.0000 (8)	0.0039 (8)	0.0026 (8)
C9	0.0386 (10)	0.0501 (12)	0.0499 (11)	−0.0001 (9)	0.0054 (8)	−0.0064 (9)
C10	0.0556 (12)	0.0497 (12)	0.0733 (14)	0.0126 (10)	0.0026 (10)	0.0093 (11)
C11	0.0558 (13)	0.0720 (16)	0.0838 (16)	−0.0081 (11)	0.0176 (12)	0.0169 (13)
C21	0.0400 (10)	0.0379 (10)	0.0473 (10)	0.0038 (8)	0.0005 (8)	−0.0019 (8)
C22	0.0410 (11)	0.0607 (14)	0.0654 (13)	−0.0006 (9)	−0.0031 (9)	−0.0045 (11)
C23	0.0416 (11)	0.0576 (14)	0.0899 (17)	−0.0072 (10)	0.0141 (11)	0.0002 (12)
C24	0.0550 (13)	0.0567 (14)	0.0746 (15)	−0.0069 (10)	0.0171 (11)	0.0122 (11)
O1	0.0700 (10)	0.0808 (12)	0.0729 (10)	0.0022 (8)	0.0074 (8)	0.0381 (9)
O2	0.0516 (8)	0.0614 (10)	0.0559 (9)	−0.0083 (7)	0.0004 (6)	0.0124 (7)
C91	0.029 (2)	0.045 (2)	0.086 (3)	0.0037 (18)	0.0108 (19)	−0.010 (3)
C92	0.038 (2)	0.058 (2)	0.098 (3)	0.010 (2)	−0.018 (2)	0.007 (2)
C93	0.049 (3)	0.076 (3)	0.138 (4)	0.009 (2)	−0.016 (3)	−0.005 (4)
C94	0.0333 (18)	0.089 (3)	0.162 (4)	0.0174 (18)	0.000 (2)	−0.018 (3)
O3	0.0495 (16)	0.090 (2)	0.105 (3)	0.0131 (13)	0.0101 (16)	−0.013 (2)
C91'	0.042 (4)	0.058 (4)	0.092 (4)	−0.003 (4)	0.017 (4)	−0.014 (4)
C92'	0.025 (3)	0.054 (3)	0.064 (4)	0.016 (3)	−0.003 (3)	0.004 (3)
C93'	0.057 (4)	0.073 (4)	0.114 (5)	0.004 (4)	−0.021 (4)	0.000 (4)
C94'	0.043 (4)	0.072 (4)	0.130 (5)	0.014 (4)	−0.009 (4)	−0.002 (5)
O3'	0.066 (4)	0.084 (3)	0.133 (4)	0.008 (3)	0.009 (4)	−0.007 (4)

N1—C9	1.464 (2)	C11—H11A	0.9600
N1—C2	1.471 (2)	C11—H11B	0.9600
N1—H1	0.89 (2)	C11—H11C	0.9600
C2—C21	1.493 (2)	C21—C22	1.344 (3)
C2—C3	1.562 (3)	C21—O2	1.370 (2)
C2—H2	0.9800	C22—C23	1.427 (3)
C3—C8	1.514 (3)	C22—H22	0.9300
C3—C10	1.525 (3)	C23—C24	1.328 (3)
C3—C4	1.548 (3)	C23—H23	0.9300
C4—C5	1.520 (3)	C24—O2	1.368 (2)
C4—H4A	0.9700	C24—H24	0.9300
C4—H4B	0.9700	C91—C92	1.342 (5)
C5—C6	1.533 (3)	C91—O3	1.393 (4)
C5—H5A	0.9700	C92—C93	1.455 (7)
C5—H5B	0.9700	C92—H92	0.9300
C6—C7	1.544 (3)	C93—C94	1.373 (7)
C6—H6A	0.9700	C93—H93	0.9300
C6—H6B	0.9700	C94—O3	1.405 (5)
C7—C8	1.517 (3)	C94—H94	0.9300
C7—C11	1.526 (3)	C91'—C92'	1.353 (8)
C7—C9	1.557 (3)	C91'—O3'	1.395 (8)
C8—O1	1.210 (2)	C92'—C93'	1.421 (7)
C9—C91	1.497 (4)	C92'—H92'	0.9300
C9—C91'	1.512 (8)	C93'—C94'	1.366 (10)
C9—H9	0.9800	C93'—H93'	0.9300
C10—H10A	0.9600	C94'—O3'	1.396 (9)
C10—H10B	0.9600	C94'—H94'	0.9300
C10—H10C	0.9600
C9—N1—C2	114.00 (15)	C3—C10—H10A	109.5
C9—N1—H1	110.0 (13)	C3—C10—H10B	109.5
C2—N1—H1	107.4 (14)	H10A—C10—H10B	109.5
N1—C2—C21	109.54 (15)	C3—C10—H10C	109.5
N1—C2—C3	111.35 (14)	H10A—C10—H10C	109.5
C21—C2—C3	113.59 (14)	H10B—C10—H10C	109.5
N1—C2—H2	107.4	C7—C11—H11A	109.5
C21—C2—H2	107.4	C7—C11—H11B	109.5
C3—C2—H2	107.4	H11A—C11—H11B	109.5
C8—C3—C10	111.32 (16)	C7—C11—H11C	109.5
C8—C3—C4	105.37 (15)	H11A—C11—H11C	109.5
C10—C3—C4	109.95 (16)	H11B—C11—H11C	109.5
C8—C3—C2	107.08 (14)	C22—C21—O2	109.35 (17)
C10—C3—C2	109.08 (15)	C22—C21—C2	132.61 (18)
C4—C3—C2	113.99 (15)	O2—C21—C2	118.04 (15)
C5—C4—C3	115.06 (16)	C21—C22—C23	106.79 (19)
C5—C4—H4A	108.5	C21—C22—H22	126.6
C3—C4—H4A	108.5	C23—C22—H22	126.6
C5—C4—H4B	108.5	C24—C23—C22	106.79 (18)
C3—C4—H4B	108.5	C24—C23—H23	126.6
H4A—C4—H4B	107.5	C22—C23—H23	126.6
C4—C5—C6	112.07 (17)	C23—C24—O2	110.22 (19)
C4—C5—H5A	109.2	C23—C24—H24	124.9
C6—C5—H5A	109.2	O2—C24—H24	124.9
C4—C5—H5B	109.2	C24—O2—C21	106.86 (16)
C6—C5—H5B	109.2	C92—C91—O3	114.7 (3)
H5A—C5—H5B	107.9	C92—C91—C9	132.1 (4)
C5—C6—C7	115.29 (16)	O3—C91—C9	113.2 (3)
C5—C6—H6A	108.5	C91—C92—C93	104.8 (4)
C7—C6—H6A	108.5	C91—C92—H92	127.6
C5—C6—H6B	108.5	C93—C92—H92	127.6
C7—C6—H6B	108.5	C94—C93—C92	106.3 (5)
H6A—C6—H6B	107.5	C94—C93—H93	126.9
C8—C7—C11	111.48 (16)	C92—C93—H93	126.9
C8—C7—C6	105.26 (15)	C93—C94—O3	111.7 (5)
C11—C7—C6	109.79 (17)	C93—C94—H94	124.2
C8—C7—C9	107.09 (15)	O3—C94—H94	124.2
C11—C7—C9	109.36 (17)	C91—O3—C94	102.6 (4)
C6—C7—C9	113.80 (16)	C92'—C91'—O3'	112.1 (7)
O1—C8—C3	122.80 (18)	C92'—C91'—C9	121.8 (8)
O1—C8—C7	122.38 (17)	O3'—C91'—C9	126.1 (8)
C3—C8—C7	114.66 (15)	C91'—C92'—C93'	103.8 (7)
N1—C9—C91	111.1 (4)	C91'—C92'—H92'	128.1
N1—C9—C91'	103.0 (10)	C93'—C92'—H92'	128.1
N1—C9—C7	111.54 (15)	C94'—C93'—C92'	111.0 (10)
C91—C9—C7	112.2 (6)	C94'—C93'—H93'	124.5
C91'—C9—C7	111.8 (15)	C92'—C93'—H93'	124.5
N1—C9—H9	107.2	C93'—C94'—O3'	106.8 (11)
C91—C9—H9	107.2	C93'—C94'—H94'	126.6
C91'—C9—H9	116.0	O3'—C94'—H94'	126.6
C7—C9—H9	107.2	C91'—O3'—C94'	106.3 (9)
C9—N1—C2—C21	−176.84 (14)	C6—C7—C9—C91'	53.2 (5)
C9—N1—C2—C3	56.7 (2)	N1—C2—C21—C22	137.4 (2)
N1—C2—C3—C8	−54.15 (19)	C3—C2—C21—C22	−97.4 (2)
C21—C2—C3—C8	−178.38 (14)	N1—C2—C21—O2	−42.4 (2)
N1—C2—C3—C10	−174.73 (15)	C3—C2—C21—O2	82.80 (19)
C21—C2—C3—C10	61.0 (2)	O2—C21—C22—C23	0.1 (2)
N1—C2—C3—C4	62.0 (2)	C2—C21—C22—C23	−179.75 (19)
C21—C2—C3—C4	−62.3 (2)	C21—C22—C23—C24	0.1 (3)
C8—C3—C4—C5	53.4 (2)	C22—C23—C24—O2	−0.2 (3)
C10—C3—C4—C5	173.44 (17)	C23—C24—O2—C21	0.3 (2)
C2—C3—C4—C5	−63.7 (2)	C22—C21—O2—C24	−0.2 (2)
C3—C4—C5—C6	−46.9 (2)	C2—C21—O2—C24	179.64 (16)
C4—C5—C6—C7	46.7 (2)	N1—C9—C91—C92	42.8 (16)
C5—C6—C7—C8	−52.7 (2)	C91'—C9—C91—C92	7 (11)
C5—C6—C7—C11	−172.77 (18)	C7—C9—C91—C92	−82.9 (14)
C5—C6—C7—C9	64.3 (2)	N1—C9—C91—O3	−138.8 (8)
C10—C3—C8—O1	−7.6 (3)	C91'—C9—C91—O3	−175 (13)
C4—C3—C8—O1	111.5 (2)	C7—C9—C91—O3	95.6 (10)
C2—C3—C8—O1	−126.8 (2)	O3—C91—C92—C93	−2.0 (13)
C10—C3—C8—C7	176.76 (16)	C9—C91—C92—C93	176.5 (14)
C4—C3—C8—C7	−64.1 (2)	C91—C92—C93—C94	1.9 (11)
C2—C3—C8—C7	57.6 (2)	C92—C93—C94—O3	−1.3 (10)
C11—C7—C8—O1	7.1 (3)	C92—C91—O3—C94	1.2 (12)
C6—C7—C8—O1	−111.9 (2)	C9—C91—O3—C94	−177.5 (8)
C9—C7—C8—O1	126.7 (2)	C93—C94—O3—C91	0.2 (10)
C11—C7—C8—C3	−177.27 (17)	N1—C9—C91'—C92'	37 (3)
C6—C7—C8—C3	63.8 (2)	C91—C9—C91'—C92'	−177 (15)
C9—C7—C8—C3	−57.7 (2)	C7—C9—C91'—C92'	−83 (3)
C2—N1—C9—C91	177.1 (5)	N1—C9—C91'—O3'	−146 (3)
C2—N1—C9—C91'	−176.8 (13)	C91—C9—C91'—O3'	0 (9)
C2—N1—C9—C7	−56.8 (2)	C7—C9—C91'—O3'	95 (3)
C8—C7—C9—N1	54.4 (2)	O3'—C91'—C92'—C93'	−1 (3)
C11—C7—C9—N1	175.29 (16)	C9—C91'—C92'—C93'	176 (3)
C6—C7—C9—N1	−61.5 (2)	C91'—C92'—C93'—C94'	3 (2)
C8—C7—C9—C91	179.8 (2)	C92'—C93'—C94'—O3'	−3 (3)
C11—C7—C9—C91	−59.3 (3)	C92'—C91'—O3'—C94'	0 (3)
C6—C7—C9—C91	63.9 (3)	C9—C91'—O3'—C94'	−178 (3)
C8—C7—C9—C91'	169.1 (5)	C93'—C94'—O3'—C91'	2 (3)
C11—C7—C9—C91'	−70.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (2)	2.84 (2)	3.647 (2)	152.0 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89 (2)	2.84 (2)	3.647 (2)	152.0 (13)

Symmetry code: (i) .