N-(Adamantan-1-yl)-2-chloro-acetamide.

In the title compound, C(12)H(18)ClNO, which was synthesized as part of a study into potential anti-tuberculosis agents, the adamantine skeleton displays shorter than normal C-C bond lengths ranging between 1.5293 (18) and 1.5366 (15) Å. The structure also displays inter-molecular N-H⋯O hydrogen bonding, which forms an infinite chain in the a-axis direction.

Related literature

For background to the title compound, see: Plakhotnik et al. (1982 ▶). For the synthesis of the title compound, see: Lee et al. (2003 ▶); Bogatcheva et al. (2006 ▶, 2010 ▶); Onajole et al. (2010 ▶). For related polycyclic structures, see: Venkataramanan et al. (2004 ▶); Fokin et al., (2009 ▶).

Experimental

Crystal data

C12H18ClNO

M = 227.72

Orthorhombic,

a = 9.3656 (2) Å

b = 13.7515 (3) Å

c = 18.7917 (4) Å

V = 2420.20 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.26 × 0.16 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.928, T max = 0.958

5629 measured reflections

3003 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.007

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.05

3003 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN; data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018046/nk2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018046/nk2092Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018046/nk2092Isup3.cml

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

C12H18ClNO	F(000) = 976
Mr = 227.72	Dx = 1.250 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5629 reflections
a = 9.3656 (2) Å	θ = 3.0–28.3°
b = 13.7515 (3) Å	µ = 0.29 mm−1
c = 18.7917 (4) Å	T = 173 K
V = 2420.20 (9) Å3	Block, colourless
Z = 8	0.26 × 0.16 × 0.15 mm

Nonius KappaCCD diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
graphite	Rint = 0.007
1.2° φ scans and ω scans	θmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.928, Tmax = 0.958	k = −18→18
5629 measured reflections	l = −24→25

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.058P)2 + 0.664P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3003 reflections	Δρmax = 0.26 e Å−3
137 parameters	Δρmin = −0.33 e Å−3
0 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: 0.0078 (14)

Experimental. X-ray single-crystal intensity data were collected on a Nonius Kappa-CCD diffractometer using graphite monochromated MoKa radiation (l = 0.71073?Å). Temperature was controlled by an Oxford Cryostream cooling system (Oxford Cryostat). The strategy for the data collections was evaluated using the Bruker Nonius "Collect" program (Nonius, 2000). Data were scaled and reduced using DENZO-SMN software (Otwinowski & Minor, 1997). Absorption corrections were performed using SADABS (Sheldrick, 2008). The structure was solved by direct methods and refined employing full-matrix least-squares with the program SHELXL97 (Sheldrick, 2008) refining on F2. All non-hydrogen atoms were refined anisotropically. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 30 mm; combination of φ and ω scans of 1.0°, 60 s per °, 2 iterations.1H NMR (CDCl3, 600 MHz): δH 1.64 (m, 6H), 1.96 (m, 6H), 2.04 (s, 3H), 3.87 (s, 2H), 6.19 (s, NH).13C NMR (CDCl3, 100 MHz); δC 29.3 (CH), 36.1 (CH2), 41.1 (CH2), 42.8 (CH2), 52.3 (C), 164.5 (C=O).

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	0.14558 (4)	0.52848 (3)	0.15642 (2)	0.04867 (14)
O1	0.10158 (8)	0.66702 (7)	0.27321 (5)	0.0342 (2)
N1	0.33518 (9)	0.70366 (7)	0.29263 (5)	0.0280 (2)
H1	0.4228	0.6889	0.2797	0.034*
C1	0.31869 (11)	0.77662 (8)	0.34943 (6)	0.0246 (2)
C2	0.23383 (13)	0.86513 (9)	0.32293 (6)	0.0316 (3)
H2A	0.2809	0.8930	0.2804	0.038*
H2B	0.1361	0.8448	0.3094	0.038*
C3	0.46993 (11)	0.80966 (9)	0.36968 (6)	0.0304 (3)
H3A	0.5262	0.7531	0.3863	0.037*
H3B	0.5182	0.8374	0.3274	0.037*
C4	0.24600 (12)	0.73351 (8)	0.41519 (6)	0.0278 (2)
H4A	0.3012	0.6769	0.4325	0.033*
H4B	0.1488	0.7110	0.4026	0.033*
C5	0.22636 (14)	0.94200 (9)	0.38192 (7)	0.0360 (3)
H5	0.1710	0.9995	0.3645	0.043*
C6	0.37733 (15)	0.97414 (9)	0.40223 (8)	0.0398 (3)
H6A	0.4255	1.0029	0.3603	0.048*
H6B	0.3726	1.0242	0.4400	0.048*
C7	0.46230 (12)	0.88638 (9)	0.42878 (7)	0.0333 (3)
H7	0.5611	0.9074	0.4418	0.040*
C8	0.38820 (13)	0.84361 (10)	0.49427 (6)	0.0343 (3)
H8A	0.3833	0.8931	0.5324	0.041*
H8B	0.4434	0.7874	0.5123	0.041*
C9	0.23705 (13)	0.81098 (9)	0.47388 (6)	0.0316 (3)
H9	0.1886	0.7827	0.5166	0.038*
C10	0.15142 (13)	0.89847 (10)	0.44707 (7)	0.0369 (3)
H10A	0.1442	0.9480	0.4851	0.044*
H10B	0.0536	0.8777	0.4341	0.044*
C11	0.22906 (11)	0.65799 (8)	0.25909 (6)	0.0275 (2)
C12	0.28360 (14)	0.59104 (11)	0.20014 (7)	0.0417 (3)
H12A	0.3506	0.5432	0.2210	0.050*
H12B	0.3370	0.6302	0.1649	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.0435 (2)	0.0562 (2)	0.0463 (2)	−0.00949 (15)	−0.01151 (14)	−0.01454 (15)
O1	0.0177 (4)	0.0510 (5)	0.0338 (4)	−0.0016 (3)	−0.0025 (3)	−0.0013 (4)
N1	0.0165 (4)	0.0365 (5)	0.0311 (5)	−0.0006 (3)	0.0008 (3)	−0.0052 (4)
C1	0.0186 (4)	0.0289 (5)	0.0263 (5)	−0.0003 (4)	−0.0003 (4)	−0.0008 (4)
C2	0.0311 (6)	0.0326 (6)	0.0313 (6)	0.0019 (5)	−0.0032 (5)	0.0047 (5)
C3	0.0196 (5)	0.0377 (6)	0.0340 (6)	−0.0036 (4)	−0.0005 (4)	−0.0040 (5)
C4	0.0259 (5)	0.0288 (5)	0.0287 (5)	−0.0026 (4)	0.0014 (4)	0.0022 (4)
C5	0.0370 (6)	0.0284 (5)	0.0425 (7)	0.0061 (5)	−0.0044 (5)	0.0009 (5)
C6	0.0448 (7)	0.0296 (6)	0.0450 (8)	−0.0077 (5)	0.0000 (6)	−0.0006 (5)
C7	0.0251 (5)	0.0375 (6)	0.0371 (6)	−0.0067 (5)	−0.0017 (4)	−0.0062 (5)
C8	0.0338 (6)	0.0390 (6)	0.0302 (6)	0.0002 (5)	−0.0050 (5)	−0.0048 (5)
C9	0.0297 (5)	0.0376 (6)	0.0274 (5)	−0.0026 (5)	0.0039 (4)	−0.0006 (5)
C10	0.0291 (6)	0.0408 (7)	0.0407 (7)	0.0054 (5)	0.0025 (5)	−0.0089 (5)
C11	0.0211 (5)	0.0350 (5)	0.0264 (5)	−0.0015 (4)	−0.0021 (4)	0.0013 (4)
C12	0.0292 (6)	0.0578 (8)	0.0380 (6)	−0.0083 (6)	0.0008 (5)	−0.0170 (6)

Cl1—C12	1.7567 (13)	C5—C10	1.5329 (19)
O1—C11	1.2293 (13)	C5—H5	1.0000
N1—C11	1.3340 (14)	C6—C7	1.5293 (18)
N1—C1	1.4729 (14)	C6—H6A	0.9900
N1—H1	0.8800	C6—H6B	0.9900
C1—C4	1.5304 (15)	C7—C8	1.5303 (17)
C1—C3	1.5354 (14)	C7—H7	1.0000
C1—C2	1.5366 (15)	C8—C9	1.5336 (16)
C2—C5	1.5334 (17)	C8—H8A	0.9900
C2—H2A	0.9900	C8—H8B	0.9900
C2—H2B	0.9900	C9—C10	1.5312 (18)
C3—C7	1.5335 (16)	C9—H9	1.0000
C3—H3A	0.9900	C10—H10A	0.9900
C3—H3B	0.9900	C10—H10B	0.9900
C4—C9	1.5357 (16)	C11—C12	1.5283 (17)
C4—H4A	0.9900	C12—H12A	0.9900
C4—H4B	0.9900	C12—H12B	0.9900
C5—C6	1.5298 (18)
C11—N1—C1	125.80 (9)	C7—C6—H6B	109.8
C11—N1—H1	117.1	C5—C6—H6B	109.8
C1—N1—H1	117.1	H6A—C6—H6B	108.2
N1—C1—C4	111.59 (9)	C6—C7—C8	109.25 (10)
N1—C1—C3	106.53 (9)	C6—C7—C3	109.32 (10)
C4—C1—C3	108.95 (9)	C8—C7—C3	109.82 (10)
N1—C1—C2	111.04 (9)	C6—C7—H7	109.5
C4—C1—C2	109.78 (9)	C8—C7—H7	109.5
C3—C1—C2	108.85 (9)	C3—C7—H7	109.5
C5—C2—C1	109.59 (9)	C7—C8—C9	109.28 (10)
C5—C2—H2A	109.8	C7—C8—H8A	109.8
C1—C2—H2A	109.8	C9—C8—H8A	109.8
C5—C2—H2B	109.8	C7—C8—H8B	109.8
C1—C2—H2B	109.8	C9—C8—H8B	109.8
H2A—C2—H2B	108.2	H8A—C8—H8B	108.3
C7—C3—C1	109.89 (9)	C10—C9—C8	109.62 (10)
C7—C3—H3A	109.7	C10—C9—C4	109.71 (10)
C1—C3—H3A	109.7	C8—C9—C4	109.39 (9)
C7—C3—H3B	109.7	C10—C9—H9	109.4
C1—C3—H3B	109.7	C8—C9—H9	109.4
H3A—C3—H3B	108.2	C4—C9—H9	109.4
C1—C4—C9	109.61 (9)	C9—C10—C5	109.26 (10)
C1—C4—H4A	109.7	C9—C10—H10A	109.8
C9—C4—H4A	109.7	C5—C10—H10A	109.8
C1—C4—H4B	109.7	C9—C10—H10B	109.8
C9—C4—H4B	109.7	C5—C10—H10B	109.8
H4A—C4—H4B	108.2	H10A—C10—H10B	108.3
C6—C5—C10	109.68 (11)	O1—C11—N1	125.04 (11)
C6—C5—C2	109.72 (10)	O1—C11—C12	122.81 (10)
C10—C5—C2	109.21 (10)	N1—C11—C12	112.15 (9)
C6—C5—H5	109.4	C11—C12—Cl1	112.84 (9)
C10—C5—H5	109.4	C11—C12—H12A	109.0
C2—C5—H5	109.4	Cl1—C12—H12A	109.0
C7—C6—C5	109.53 (10)	C11—C12—H12B	109.0
C7—C6—H6A	109.8	Cl1—C12—H12B	109.0
C5—C6—H6A	109.8	H12A—C12—H12B	107.8
C11—N1—C1—C4	62.57 (14)	C5—C6—C7—C3	59.83 (13)
C11—N1—C1—C3	−178.63 (11)	C1—C3—C7—C6	−60.28 (13)
C11—N1—C1—C2	−60.26 (14)	C1—C3—C7—C8	59.57 (13)
N1—C1—C2—C5	−176.69 (9)	C6—C7—C8—C9	60.43 (13)
C4—C1—C2—C5	59.45 (12)	C3—C7—C8—C9	−59.46 (13)
C3—C1—C2—C5	−59.73 (12)	C7—C8—C9—C10	−60.35 (13)
N1—C1—C3—C7	179.85 (9)	C7—C8—C9—C4	59.99 (13)
C4—C1—C3—C7	−59.64 (12)	C1—C4—C9—C10	59.49 (12)
C2—C1—C3—C7	60.05 (12)	C1—C4—C9—C8	−60.79 (12)
N1—C1—C4—C9	177.60 (9)	C8—C9—C10—C5	59.74 (13)
C3—C1—C4—C9	60.26 (11)	C4—C9—C10—C5	−60.40 (13)
C2—C1—C4—C9	−58.85 (12)	C6—C5—C10—C9	−59.57 (13)
C1—C2—C5—C6	60.02 (13)	C2—C5—C10—C9	60.70 (13)
C1—C2—C5—C10	−60.23 (13)	C1—N1—C11—O1	−3.61 (19)
C10—C5—C6—C7	60.04 (14)	C1—N1—C11—C12	176.78 (10)
C2—C5—C6—C7	−59.92 (14)	O1—C11—C12—Cl1	−0.73 (17)
C5—C6—C7—C8	−60.38 (13)	N1—C11—C12—Cl1	178.88 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	1.97	2.8301 (12)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	1.97	2.8301 (12)	165

Symmetry code: (i) .