2,2-Dichloro-1-(3,3,6-trimethyl-9-oxo-1,5-diaza-bicyclo-[4.3.0]nonan-5-yl)ethanone.

In the title mol-ecule, C(12)H(18)Cl(2)N(2)O(2), the six-membered ring is in a chair conformation and the five-membered ring is in an envelope conformation. In the crystal, weak inter-molecular bifurcated (C-H)(2)⋯O hydrogen bonds connect mol-ecules into chains along [010].

Related literature

For synthetic applications of 1,5-diaza­bicyclo compounds, see: Hutton & Bartlett (2007) ▶; Koptelov et al. (2011 ▶); Taylor et al. (2010 ▶). For the bioactivity of N-dichloro­acety diaza­bicyclo derivatives, see: Burton et al. (1994 ▶); Hatzios (2004 ▶); Loniovereror (1993 ▶). For the synthetic procedure, see: Sun & Ye (2010 ▶).

Experimental

Crystal data

C12H18Cl2N2O2

M = 293.18

Monoclinic,

a = 9.4442 (18) Å

b = 14.116 (3) Å

c = 11.7555 (16) Å

β = 115.067 (11)°

V = 1419.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 K

0.42 × 0.40 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.832, T max = 0.884

10829 measured reflections

3492 independent reflections

2556 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.04

3492 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008) ▶; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027176/lh5271sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027176/lh5271Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027176/lh5271Isup3.cml

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

C12H18Cl2N2O2	F(000) = 616
Mr = 293.18	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3515 reflections
a = 9.4442 (18) Å	θ = 2.4–27.1°
b = 14.116 (3) Å	µ = 0.45 mm−1
c = 11.7555 (16) Å	T = 298 K
β = 115.067 (11)°	Block, colourless
V = 1419.6 (4) Å3	0.42 × 0.40 × 0.28 mm
Z = 4

Bruker SMART CCD diffractometer	3492 independent reflections
Radiation source: fine-focus sealed tube	2556 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.832, Tmax = 0.884	k = −18→18
10829 measured reflections	l = −9→15

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) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.2384P] where P = (Fo2 + 2Fc2)/3
3492 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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
Cl1	0.38732 (6)	−0.01048 (4)	0.34216 (5)	0.05901 (18)
Cl2	0.21200 (7)	−0.01735 (4)	0.07141 (6)	0.0696 (2)
O1	0.43042 (15)	−0.18995 (10)	0.24212 (16)	0.0618 (4)
O2	0.06902 (18)	−0.54370 (10)	0.24058 (16)	0.0638 (4)
N1	0.17907 (15)	−0.24099 (9)	0.17670 (13)	0.0342 (3)
N2	0.10521 (16)	−0.40443 (10)	0.15860 (14)	0.0388 (3)
C1	0.2408 (2)	−0.07096 (12)	0.21585 (17)	0.0419 (4)
H1	0.1428	−0.0703	0.2257	0.050*
C2	0.29300 (19)	−0.17366 (12)	0.21273 (17)	0.0399 (4)
C3	0.01328 (18)	−0.21728 (12)	0.09737 (15)	0.0364 (4)
H3A	−0.0029	−0.2147	0.0102	0.044*
H3B	−0.0089	−0.1549	0.1205	0.044*
C4	−0.10098 (18)	−0.28847 (12)	0.10984 (15)	0.0366 (4)
C5	−0.2656 (2)	−0.26170 (16)	0.0151 (2)	0.0581 (5)
H5A	−0.2699	−0.2615	−0.0679	0.087*
H5B	−0.2913	−0.1998	0.0346	0.087*
H5C	−0.3392	−0.3070	0.0193	0.087*
C6	−0.0909 (2)	−0.28828 (14)	0.24271 (18)	0.0485 (4)
H6A	−0.1645	−0.3329	0.2480	0.073*
H6B	−0.1148	−0.2261	0.2627	0.073*
H6C	0.0128	−0.3057	0.3011	0.073*
C7	−0.0579 (2)	−0.38544 (12)	0.07744 (17)	0.0419 (4)
H7A	−0.1235	−0.4337	0.0893	0.050*
H7B	−0.0742	−0.3866	−0.0098	0.050*
C8	0.22976 (19)	−0.33990 (11)	0.16558 (16)	0.0367 (4)
C9	0.2611 (2)	−0.34929 (15)	0.04896 (19)	0.0516 (5)
H9A	0.2991	−0.4119	0.0457	0.077*
H9B	0.3380	−0.3035	0.0525	0.077*
H9C	0.1660	−0.3384	−0.0247	0.077*
C10	0.3679 (2)	−0.37342 (13)	0.28688 (18)	0.0477 (4)
H10A	0.4655	−0.3695	0.2784	0.057*
H10B	0.3763	−0.3353	0.3582	0.057*
C11	0.3290 (2)	−0.47623 (14)	0.3029 (2)	0.0531 (5)
H11A	0.3784	−0.5195	0.2666	0.064*
H11B	0.3628	−0.4917	0.3909	0.064*
C12	0.1545 (2)	−0.48091 (12)	0.23385 (19)	0.0454 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0585 (3)	0.0609 (3)	0.0632 (3)	−0.0227 (2)	0.0313 (3)	−0.0199 (2)
Cl2	0.0747 (4)	0.0676 (4)	0.0629 (4)	0.0028 (3)	0.0257 (3)	0.0219 (3)
O1	0.0345 (7)	0.0509 (8)	0.0934 (12)	−0.0021 (6)	0.0206 (7)	−0.0014 (7)
O2	0.0683 (9)	0.0460 (7)	0.0921 (12)	0.0003 (7)	0.0483 (9)	0.0128 (8)
N1	0.0325 (7)	0.0336 (6)	0.0362 (7)	−0.0005 (5)	0.0141 (6)	−0.0005 (5)
N2	0.0405 (8)	0.0346 (7)	0.0426 (8)	−0.0015 (6)	0.0189 (6)	−0.0034 (6)
C1	0.0399 (9)	0.0389 (9)	0.0505 (10)	−0.0074 (7)	0.0226 (8)	−0.0032 (8)
C2	0.0360 (9)	0.0392 (8)	0.0431 (9)	−0.0025 (7)	0.0156 (8)	−0.0012 (7)
C3	0.0345 (8)	0.0391 (8)	0.0329 (8)	0.0000 (6)	0.0116 (7)	0.0019 (7)
C4	0.0336 (8)	0.0387 (8)	0.0359 (8)	−0.0028 (6)	0.0133 (7)	−0.0029 (7)
C5	0.0363 (10)	0.0621 (12)	0.0633 (13)	−0.0026 (9)	0.0089 (9)	0.0008 (10)
C6	0.0567 (11)	0.0495 (10)	0.0487 (11)	−0.0041 (8)	0.0313 (9)	−0.0047 (8)
C7	0.0418 (9)	0.0404 (9)	0.0412 (9)	−0.0073 (7)	0.0153 (8)	−0.0097 (7)
C8	0.0367 (8)	0.0344 (8)	0.0414 (9)	−0.0001 (6)	0.0189 (7)	−0.0026 (7)
C9	0.0573 (11)	0.0563 (11)	0.0524 (11)	0.0039 (9)	0.0342 (10)	−0.0030 (9)
C10	0.0419 (10)	0.0461 (10)	0.0507 (11)	0.0072 (8)	0.0153 (9)	0.0024 (8)
C11	0.0530 (11)	0.0509 (11)	0.0594 (12)	0.0123 (9)	0.0278 (10)	0.0129 (9)
C12	0.0565 (11)	0.0381 (9)	0.0533 (11)	0.0051 (8)	0.0345 (10)	0.0008 (8)

Cl1—C1	1.7627 (18)	C5—H5B	0.9600
Cl2—C1	1.7715 (19)	C5—H5C	0.9600
O1—C2	1.215 (2)	C6—H6A	0.9600
O2—C12	1.224 (2)	C6—H6B	0.9600
N1—C2	1.362 (2)	C6—H6C	0.9600
N1—C3	1.482 (2)	C7—H7A	0.9700
N1—C8	1.499 (2)	C7—H7B	0.9700
N2—C12	1.348 (2)	C8—C9	1.526 (2)
N2—C7	1.452 (2)	C8—C10	1.544 (2)
N2—C8	1.462 (2)	C9—H9A	0.9600
C1—C2	1.537 (2)	C9—H9B	0.9600
C1—H1	0.9800	C9—H9C	0.9600
C3—C4	1.527 (2)	C10—C11	1.528 (3)
C3—H3A	0.9700	C10—H10A	0.9700
C3—H3B	0.9700	C10—H10B	0.9700
C4—C7	1.522 (2)	C11—C12	1.499 (3)
C4—C6	1.524 (2)	C11—H11A	0.9700
C4—C5	1.528 (2)	C11—H11B	0.9700
C5—H5A	0.9600
C2—N1—C3	121.54 (13)	C4—C6—H6C	109.5
C2—N1—C8	115.95 (13)	H6A—C6—H6C	109.5
C3—N1—C8	116.53 (12)	H6B—C6—H6C	109.5
C12—N2—C7	123.66 (15)	N2—C7—C4	108.86 (13)
C12—N2—C8	114.61 (15)	N2—C7—H7A	109.9
C7—N2—C8	121.72 (14)	C4—C7—H7A	109.9
C2—C1—Cl1	109.38 (12)	N2—C7—H7B	109.9
C2—C1—Cl2	107.50 (13)	C4—C7—H7B	109.9
Cl1—C1—Cl2	110.34 (9)	H7A—C7—H7B	108.3
C2—C1—H1	109.9	N2—C8—N1	107.82 (13)
Cl1—C1—H1	109.9	N2—C8—C9	110.68 (14)
Cl2—C1—H1	109.9	N1—C8—C9	110.48 (14)
O1—C2—N1	124.36 (16)	N2—C8—C10	101.88 (14)
O1—C2—C1	119.10 (15)	N1—C8—C10	112.40 (13)
N1—C2—C1	116.54 (14)	C9—C8—C10	113.16 (15)
N1—C3—C4	113.10 (13)	C8—C9—H9A	109.5
N1—C3—H3A	109.0	C8—C9—H9B	109.5
C4—C3—H3A	109.0	H9A—C9—H9B	109.5
N1—C3—H3B	109.0	C8—C9—H9C	109.5
C4—C3—H3B	109.0	H9A—C9—H9C	109.5
H3A—C3—H3B	107.8	H9B—C9—H9C	109.5
C7—C4—C6	110.55 (14)	C11—C10—C8	104.57 (15)
C7—C4—C3	107.05 (14)	C11—C10—H10A	110.8
C6—C4—C3	110.96 (14)	C8—C10—H10A	110.8
C7—C4—C5	109.74 (15)	C11—C10—H10B	110.8
C6—C4—C5	110.41 (16)	C8—C10—H10B	110.8
C3—C4—C5	108.05 (15)	H10A—C10—H10B	108.9
C4—C5—H5A	109.5	C12—C11—C10	104.01 (15)
C4—C5—H5B	109.5	C12—C11—H11A	111.0
H5A—C5—H5B	109.5	C10—C11—H11A	111.0
C4—C5—H5C	109.5	C12—C11—H11B	111.0
H5A—C5—H5C	109.5	C10—C11—H11B	111.0
H5B—C5—H5C	109.5	H11A—C11—H11B	109.0
C4—C6—H6A	109.5	O2—C12—N2	124.68 (19)
C4—C6—H6B	109.5	O2—C12—C11	126.95 (18)
H6A—C6—H6B	109.5	N2—C12—C11	108.34 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.98	2.23	3.200 (3)	170
C3—H3B···O2i	0.97	2.50	3.390 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.98	2.23	3.200 (3)	170
C3—H3B⋯O2i	0.97	2.50	3.390 (2)	153

Symmetry code: (i) .