(S)-2-Amino-2-(2-chloro-phen-yl)cyclo-hexa-none.

The crystal structure of the title compound, C(12)H(14)ClNO, was determined in order to confirm that the chiral center of the mol-ecule has an S configuration. The cyclo-hexa-none ring adopts a chair conformation. The 2-chloro-phenyl ring is slightly twisted from the axial C-N bond, with a N-C-C-C torsion angle of -5.7 (2)°. In the crystal, an inter-molecular N-H⋯O hydrogen bond links adjacent mol-ecules into an infinite chain, which propagates in the b-axis direction.

Related literature

For background literature on the preparation and use of some anesthetics, see: Holtman et al. (2006 ▶); Heshmati et al. (2003 ▶); Kohrs & Durieux (1998 ▶). For information on the synthetic transformations used, see: Kolb et al. (1994 ▶); Parcell & Sanchez (1981 ▶); Senanayake et al. (1996 ▶); Yang & Davisson (1985 ▶).

Experimental

Crystal data

C12H14ClNO

M = 223.69

Orthorhombic,

a = 7.2437 (5) Å

b = 7.4244 (5) Å

c = 20.4794 (15) Å

V = 1101.38 (13) Å3

Z = 4

Cu Kα radiation

μ = 2.84 mm−1

T = 173 K

0.43 × 0.15 × 0.03 mm

Data collection

Bruker SMART APEX II diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.375, T max = 0.920

3449 measured reflections

1538 independent reflections

1521 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.059

S = 1.01

1538 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 545 Friedel pairs

Flack parameter: 0.060 (13)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009950/nk2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009950/nk2080Isup2.hkl

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

C12H14ClNO	F(000) = 472
Mr = 223.69	Dx = 1.349 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3161 reflections
a = 7.2437 (5) Å	θ = 4.3–64.6°
b = 7.4244 (5) Å	µ = 2.84 mm−1
c = 20.4794 (15) Å	T = 173 K
V = 1101.38 (13) Å3	Block, colourless
Z = 4	0.43 × 0.15 × 0.03 mm

Bruker SMART APEX II diffractometer	1538 independent reflections
Radiation source: fine-focus sealed tube	1521 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 64.7°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.375, Tmax = 0.920	k = −8→8
3449 measured reflections	l = −24→19

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)] = 0.023	H-atom parameters constrained
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0302P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1538 reflections	Δρmax = 0.14 e Å−3
136 parameters	Δρmin = −0.15 e Å−3
0 restraints	Absolute structure: Flack (1983), 545 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.060 (13)

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.There were problems during data colleciton that were only realised after refinement of the results. The data were quite weak at high angle and although data were collected out to 0.85 Angstrons, the processed data were only 89% complete; however the overall statistics and quality of the results appeared quite good.

	x	y	z	Uiso*/Ueq
C1	0.2928 (2)	0.4934 (2)	0.84577 (8)	0.0241 (3)
C2	0.4469 (2)	0.3899 (2)	0.88115 (7)	0.0248 (4)
C3	0.5543 (3)	0.4618 (2)	0.93085 (7)	0.0288 (4)
C4	0.6938 (3)	0.3647 (2)	0.96124 (9)	0.0389 (4)
H4	0.7637	0.4178	0.9954	0.047*
C5	0.7303 (3)	0.1905 (3)	0.94148 (10)	0.0463 (5)
H5	0.8264	0.1236	0.9617	0.056*
C6	0.6268 (3)	0.1144 (2)	0.89243 (10)	0.0434 (5)
H6	0.6508	−0.0055	0.8787	0.052*
C7	0.4874 (3)	0.2131 (2)	0.86316 (8)	0.0336 (4)
H7	0.4166	0.1583	0.8295	0.040*
C8	0.1313 (2)	0.5361 (2)	0.89240 (8)	0.0301 (4)
H8A	0.0653	0.4228	0.9026	0.036*
H8B	0.1822	0.5838	0.9338	0.036*
C9	−0.0066 (2)	0.6718 (2)	0.86506 (9)	0.0379 (4)
H9A	−0.0712	0.6184	0.8271	0.045*
H9B	−0.1001	0.7003	0.8988	0.045*
C10	0.0903 (3)	0.8435 (2)	0.84417 (9)	0.0380 (4)
H10A	0.1524	0.8986	0.8823	0.046*
H10B	−0.0018	0.9306	0.8274	0.046*
C11	0.2330 (3)	0.8039 (2)	0.79098 (8)	0.0340 (4)
H11A	0.1691	0.7598	0.7514	0.041*
H11B	0.2986	0.9165	0.7795	0.041*
C12	0.3715 (2)	0.6647 (2)	0.81317 (7)	0.0258 (4)
Cl1	0.52113 (6)	0.68279 (5)	0.958904 (19)	0.03641 (13)
N1	0.2147 (2)	0.39391 (19)	0.79034 (7)	0.0358 (3)
H1A	0.3079	0.3550	0.7641	0.054*
H1B	0.1502	0.2974	0.8055	0.054*
O1	0.53524 (16)	0.67977 (16)	0.80222 (6)	0.0351 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0209 (9)	0.0303 (7)	0.0211 (8)	−0.0004 (7)	−0.0008 (7)	−0.0029 (6)
C2	0.0218 (9)	0.0330 (8)	0.0197 (8)	−0.0022 (6)	0.0041 (7)	0.0037 (6)
C3	0.0267 (10)	0.0373 (8)	0.0223 (8)	−0.0045 (7)	0.0038 (7)	0.0031 (6)
C4	0.0300 (10)	0.0599 (11)	0.0267 (9)	−0.0057 (8)	−0.0052 (8)	0.0135 (8)
C5	0.0389 (11)	0.0555 (11)	0.0444 (11)	0.0114 (10)	0.0014 (9)	0.0248 (9)
C6	0.0478 (13)	0.0346 (9)	0.0477 (12)	0.0070 (8)	0.0074 (10)	0.0117 (8)
C7	0.0382 (11)	0.0326 (7)	0.0300 (9)	−0.0014 (8)	0.0040 (8)	0.0029 (6)
C8	0.0232 (9)	0.0409 (9)	0.0262 (9)	−0.0019 (7)	0.0036 (7)	−0.0012 (7)
C9	0.0234 (9)	0.0546 (10)	0.0357 (9)	0.0059 (10)	0.0011 (7)	−0.0063 (7)
C10	0.0345 (10)	0.0427 (9)	0.0367 (10)	0.0112 (8)	−0.0040 (8)	−0.0027 (8)
C11	0.0351 (10)	0.0375 (8)	0.0293 (8)	0.0039 (8)	−0.0035 (8)	0.0031 (7)
C12	0.0279 (10)	0.0344 (8)	0.0150 (7)	0.0001 (7)	−0.0020 (6)	−0.0016 (6)
Cl1	0.0387 (2)	0.0428 (2)	0.0278 (2)	−0.00777 (19)	−0.00231 (17)	−0.00948 (14)
N1	0.0314 (9)	0.0453 (7)	0.0307 (8)	−0.0022 (7)	−0.0032 (7)	−0.0123 (6)
O1	0.0266 (7)	0.0477 (6)	0.0310 (6)	−0.0013 (6)	0.0023 (5)	0.0107 (5)

C1—N1	1.468 (2)	C8—C9	1.525 (2)
C1—C2	1.537 (2)	C8—H8A	0.9900
C1—C8	1.543 (2)	C8—H8B	0.9900
C1—C12	1.545 (2)	C9—C10	1.517 (3)
C2—C3	1.388 (2)	C9—H9A	0.9900
C2—C7	1.394 (2)	C9—H9B	0.9900
C3—C4	1.389 (3)	C10—C11	1.530 (3)
C3—Cl1	1.7548 (16)	C10—H10A	0.9900
C4—C5	1.380 (3)	C10—H10B	0.9900
C4—H4	0.9500	C11—C12	1.511 (2)
C5—C6	1.375 (3)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.384 (3)	C12—O1	1.212 (2)
C6—H6	0.9500	N1—H1A	0.9100
C7—H7	0.9500	N1—H1B	0.9100
N1—C1—C2	113.13 (13)	C9—C8—H8B	108.8
N1—C1—C8	106.87 (14)	C1—C8—H8B	108.8
C2—C1—C8	111.20 (13)	H8A—C8—H8B	107.7
N1—C1—C12	102.84 (13)	C10—C9—C8	110.82 (15)
C2—C1—C12	110.31 (13)	C10—C9—H9A	109.5
C8—C1—C12	112.21 (13)	C8—C9—H9A	109.5
C3—C2—C7	115.98 (16)	C10—C9—H9B	109.5
C3—C2—C1	124.08 (15)	C8—C9—H9B	109.5
C7—C2—C1	119.93 (15)	H9A—C9—H9B	108.1
C2—C3—C4	122.46 (16)	C9—C10—C11	110.58 (15)
C2—C3—Cl1	121.54 (13)	C9—C10—H10A	109.5
C4—C3—Cl1	116.01 (14)	C11—C10—H10A	109.5
C5—C4—C3	119.62 (18)	C9—C10—H10B	109.5
C5—C4—H4	120.2	C11—C10—H10B	109.5
C3—C4—H4	120.2	H10A—C10—H10B	108.1
C6—C5—C4	119.67 (18)	C12—C11—C10	111.48 (14)
C6—C5—H5	120.2	C12—C11—H11A	109.3
C4—C5—H5	120.2	C10—C11—H11A	109.3
C5—C6—C7	119.77 (18)	C12—C11—H11B	109.3
C5—C6—H6	120.1	C10—C11—H11B	109.3
C7—C6—H6	120.1	H11A—C11—H11B	108.0
C6—C7—C2	122.49 (18)	O1—C12—C11	122.06 (16)
C6—C7—H7	118.8	O1—C12—C1	121.14 (16)
C2—C7—H7	118.8	C11—C12—C1	116.62 (15)
C9—C8—C1	113.91 (15)	C1—N1—H1A	109.3
C9—C8—H8A	108.8	C1—N1—H1B	109.2
C1—C8—H8A	108.8	H1A—N1—H1B	109.5
N1—C1—C2—C3	173.46 (15)	C1—C2—C7—C6	178.79 (17)
C8—C1—C2—C3	−66.3 (2)	N1—C1—C8—C9	−68.43 (18)
C12—C1—C2—C3	58.89 (19)	C2—C1—C8—C9	167.66 (14)
N1—C1—C2—C7	−5.7 (2)	C12—C1—C8—C9	43.57 (19)
C8—C1—C2—C7	114.58 (16)	C1—C8—C9—C10	−54.5 (2)
C12—C1—C2—C7	−120.26 (15)	C8—C9—C10—C11	60.3 (2)
C7—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	−56.4 (2)
C1—C2—C3—C4	−179.30 (15)	C10—C11—C12—O1	−137.39 (18)
C7—C2—C3—Cl1	179.79 (12)	C10—C11—C12—C1	47.45 (19)
C1—C2—C3—Cl1	0.6 (2)	N1—C1—C12—O1	−101.44 (18)
C2—C3—C4—C5	0.7 (3)	C2—C1—C12—O1	19.5 (2)
Cl1—C3—C4—C5	−179.21 (14)	C8—C1—C12—O1	144.07 (16)
C3—C4—C5—C6	−0.7 (3)	N1—C1—C12—C11	73.77 (17)
C4—C5—C6—C7	0.2 (3)	C2—C1—C12—C11	−165.31 (14)
C5—C6—C7—C2	0.4 (3)	C8—C1—C12—C11	−40.72 (19)
C3—C2—C7—C6	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.91	2.20	3.066 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.91	2.20	3.066 (2)	160

Symmetry code: (i) .