(S)-1-(2-Chloro-phen-yl)-2-oxocyclo-hexan-1-aminium d-tartrate.

In the title compound, C(12)H(15)ClNO(+)·C(4)H(5)O(6) (-), the cyclo-hexa-none ring adopts a chair conformation. The benzene ring is significantly twisted so that it is in an almost perpendicular position to the C-N bond with a C(Ar)-C(Ar)-C-N torsion angle of -96.5 (5)°. Intermolecular N-H⋯O and O-H⋯O hydrogen bonds are observed in the crystal structure.

Related literature

For background to ketamine, see: Holtman (2006 ▶); Holtman et al. (2006 ▶); Heshmati et al. (2003 ▶); Kohrs & Durieux (1998 ▶). For the synthesis, see: Hong & Davisson (1982 ▶); Parcell & Sanchez (1981 ▶).

Experimental

Crystal data

C12H15ClNO+·C4H5O6 −

M = 373.78

Orthorhombic,

a = 7.1411 (2) Å

b = 9.9878 (4) Å

c = 23.7530 (11) Å

V = 1694.16 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 90 K

0.20 × 0.20 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.949, T max = 0.992

13735 measured reflections

2986 independent reflections

1519 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.139

S = 0.96

2986 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1241 Friedel pairs

Flack parameter: 0.10 (10)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006131/hg2766sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006131/hg2766Isup2.hkl

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

C12H15ClNO+·C4H5O6−	F(000) = 784
Mr = 373.78	Dx = 1.465 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2155 reflections
a = 7.1411 (2) Å	θ = 1.0–27.5°
b = 9.9878 (4) Å	µ = 0.27 mm−1
c = 23.7530 (11) Å	T = 90 K
V = 1694.16 (11) Å3	Plate, colourless
Z = 4	0.20 × 0.20 × 0.03 mm

Nonius KappaCCD diffractometer	2986 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
graphite	Rint = 0.110
Detector resolution: 9.1 pixels mm-1	θmax = 25.0°, θmin = 1.7°
ω scans at fixed χ = 55°	h = −8→8
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −11→11
Tmin = 0.949, Tmax = 0.992	l = −27→28
13735 measured reflections

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0568P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2986 reflections	Δρmax = 0.28 e Å−3
230 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 1241 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (10)

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 > 2σ(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	0.3664 (2)	0.71723 (16)	0.91603 (9)	0.0776 (7)
O1	0.4054 (5)	0.4009 (4)	0.92986 (16)	0.0391 (11)
N1	0.5914 (5)	0.4734 (4)	0.83868 (16)	0.0254 (12)
H1A	0.6786	0.4352	0.8158	0.038*
H1B	0.5453	0.5485	0.8220	0.038*
H1C	0.4964	0.4144	0.8448	0.038*
C1	0.5939 (7)	0.7596 (6)	0.8988 (2)	0.0418 (17)
C2	0.6335 (10)	0.8933 (6)	0.8922 (3)	0.057 (2)
H2	0.5381	0.9585	0.8973	0.069*
C3	0.8128 (10)	0.9322 (6)	0.8779 (2)	0.0449 (18)
H3	0.8403	1.0242	0.8720	0.054*
C4	0.9520 (9)	0.8374 (6)	0.8723 (2)	0.0339 (15)
H4	1.0764	0.8643	0.8638	0.041*
C5	0.9097 (7)	0.7021 (5)	0.8790 (2)	0.0282 (15)
H5	1.0058	0.6375	0.8740	0.034*
C6	0.7292 (7)	0.6595 (5)	0.8931 (2)	0.0246 (14)
C7	0.6805 (7)	0.5100 (5)	0.8940 (2)	0.0226 (13)
C8	0.8535 (7)	0.4174 (5)	0.9031 (2)	0.0291 (14)
H8A	0.8155	0.3229	0.8978	0.035*
H8B	0.9501	0.4387	0.8746	0.035*
C9	0.9367 (8)	0.4348 (6)	0.9620 (2)	0.0399 (16)
H9A	1.0470	0.3756	0.9662	0.048*
H9B	0.9791	0.5285	0.9669	0.048*
C10	0.7954 (9)	0.4015 (6)	1.0067 (2)	0.0489 (18)
H10A	0.8503	0.4184	1.0443	0.059*
H10B	0.7626	0.3054	1.0043	0.059*
C11	0.6186 (9)	0.4861 (7)	0.9995 (2)	0.0505 (19)
H11A	0.5231	0.4588	1.0274	0.061*
H11B	0.6481	0.5819	1.0055	0.061*
C12	0.5447 (9)	0.4655 (5)	0.9409 (2)	0.0321 (14)
C13	0.5503 (8)	0.6596 (5)	0.6984 (3)	0.0266 (14)
C14	0.7637 (7)	0.6537 (5)	0.6976 (2)	0.0242 (14)
H14	0.8039	0.5662	0.7141	0.029*
C15	0.8443 (7)	0.7649 (5)	0.7331 (2)	0.0218 (13)
H15	0.7942	0.7538	0.7721	0.026*
C16	1.0558 (8)	0.7639 (6)	0.7370 (2)	0.0255 (14)
O2	0.8330 (5)	0.6619 (4)	0.64159 (14)	0.0297 (10)
H2A	0.7541	0.7012	0.6212	0.045*
O3	0.4634 (5)	0.6867 (3)	0.65555 (16)	0.0291 (10)
O4	0.4745 (5)	0.6434 (3)	0.74860 (16)	0.0334 (10)
O5	0.7747 (5)	0.8881 (3)	0.71191 (15)	0.0287 (10)
H5A	0.8366	0.9517	0.7257	0.043*
O6	1.1301 (5)	0.6502 (3)	0.74840 (16)	0.0304 (9)
H6	1.2464	0.6547	0.7436	0.046*
O7	1.1404 (5)	0.8705 (3)	0.72982 (14)	0.0269 (9)

	U11	U22	U33	U12	U13	U23
Cl1	0.0331 (10)	0.0394 (9)	0.160 (2)	0.0090 (9)	0.0157 (11)	−0.0109 (12)
O1	0.029 (3)	0.038 (2)	0.050 (3)	−0.0149 (19)	0.003 (2)	−0.008 (2)
N1	0.025 (3)	0.019 (2)	0.032 (3)	0.001 (2)	0.000 (2)	−0.002 (2)
C1	0.031 (4)	0.027 (4)	0.068 (5)	0.004 (3)	−0.004 (3)	−0.005 (3)
C2	0.045 (4)	0.030 (4)	0.096 (6)	0.009 (4)	−0.009 (4)	−0.008 (4)
C3	0.066 (5)	0.026 (4)	0.042 (4)	−0.011 (4)	−0.025 (4)	−0.004 (3)
C4	0.041 (4)	0.033 (4)	0.028 (3)	−0.009 (3)	0.003 (3)	0.003 (3)
C5	0.030 (4)	0.029 (4)	0.026 (3)	−0.006 (3)	−0.002 (3)	0.001 (3)
C6	0.031 (3)	0.026 (3)	0.017 (3)	−0.001 (3)	−0.001 (3)	0.000 (3)
C7	0.024 (3)	0.021 (3)	0.023 (3)	−0.005 (3)	−0.005 (3)	−0.001 (3)
C8	0.030 (3)	0.021 (3)	0.036 (4)	0.001 (3)	−0.005 (3)	0.005 (3)
C9	0.043 (4)	0.037 (4)	0.040 (4)	0.000 (3)	−0.004 (4)	0.010 (3)
C10	0.053 (5)	0.055 (5)	0.039 (4)	−0.008 (4)	−0.010 (4)	0.010 (4)
C11	0.056 (5)	0.068 (5)	0.027 (4)	−0.013 (4)	0.016 (4)	−0.004 (4)
C12	0.035 (4)	0.028 (4)	0.033 (4)	0.009 (3)	0.005 (3)	−0.001 (3)
C13	0.023 (3)	0.014 (3)	0.043 (4)	−0.003 (3)	−0.007 (3)	0.005 (3)
C14	0.023 (3)	0.022 (3)	0.028 (4)	−0.002 (3)	0.002 (3)	0.010 (3)
C15	0.018 (3)	0.023 (3)	0.025 (3)	0.003 (3)	0.001 (3)	0.003 (3)
C16	0.031 (4)	0.030 (4)	0.016 (3)	0.006 (3)	0.007 (3)	0.001 (3)
O2	0.030 (2)	0.031 (2)	0.028 (2)	0.004 (2)	−0.0047 (19)	−0.0057 (18)
O3	0.025 (2)	0.022 (2)	0.040 (2)	0.0016 (18)	−0.012 (2)	0.0039 (19)
O4	0.027 (2)	0.035 (2)	0.039 (2)	−0.0003 (19)	−0.005 (2)	0.010 (2)
O5	0.028 (2)	0.014 (2)	0.044 (2)	0.0049 (17)	−0.0106 (19)	−0.0062 (19)
O6	0.013 (2)	0.027 (2)	0.052 (3)	0.0024 (19)	0.002 (2)	0.010 (2)
O7	0.027 (2)	0.023 (2)	0.031 (2)	−0.0046 (19)	0.0049 (19)	0.0026 (18)

Cl1—C1	1.728 (6)	C9—H9A	0.9900
O1—C12	1.214 (6)	C9—H9B	0.9900
N1—C7	1.505 (6)	C10—C11	1.529 (8)
N1—H1A	0.9100	C10—H10A	0.9900
N1—H1B	0.9100	C10—H10B	0.9900
N1—H1C	0.9100	C11—C12	1.503 (8)
C1—C2	1.374 (8)	C11—H11A	0.9900
C1—C6	1.397 (7)	C11—H11B	0.9900
C2—C3	1.380 (8)	C13—O3	1.223 (6)
C2—H2	0.9500	C13—O4	1.320 (6)
C3—C4	1.379 (7)	C13—C14	1.525 (7)
C3—H3	0.9500	C14—O2	1.423 (5)
C4—C5	1.393 (7)	C14—C15	1.508 (6)
C4—H4	0.9500	C14—H14	1.0000
C5—C6	1.398 (7)	C15—O5	1.419 (5)
C5—H5	0.9500	C15—C16	1.513 (6)
C6—C7	1.533 (7)	C15—H15	1.0000
C7—C12	1.542 (7)	C16—O7	1.237 (6)
C7—C8	1.558 (7)	C16—O6	1.282 (6)
C8—C9	1.531 (7)	O2—H2A	0.8400
C8—H8A	0.9900	O5—H5A	0.8400
C8—H8B	0.9900	O6—H6	0.8400
C9—C10	1.501 (7)
C7—N1—H1A	109.5	C10—C9—H9B	109.4
C7—N1—H1B	109.5	C8—C9—H9B	109.4
H1A—N1—H1B	109.5	H9A—C9—H9B	108.0
C7—N1—H1C	109.5	C9—C10—C11	110.7 (5)
H1A—N1—H1C	109.5	C9—C10—H10A	109.5
H1B—N1—H1C	109.5	C11—C10—H10A	109.5
C2—C1—C6	122.9 (6)	C9—C10—H10B	109.5
C2—C1—Cl1	117.3 (5)	C11—C10—H10B	109.5
C6—C1—Cl1	119.8 (4)	H10A—C10—H10B	108.1
C1—C2—C3	119.5 (6)	C12—C11—C10	108.5 (5)
C1—C2—H2	120.2	C12—C11—H11A	110.0
C3—C2—H2	120.2	C10—C11—H11A	110.0
C4—C3—C2	119.9 (6)	C12—C11—H11B	110.0
C4—C3—H3	120.0	C10—C11—H11B	110.0
C2—C3—H3	120.0	H11A—C11—H11B	108.4
C3—C4—C5	119.9 (6)	O1—C12—C11	124.0 (6)
C3—C4—H4	120.1	O1—C12—C7	120.9 (5)
C5—C4—H4	120.1	C11—C12—C7	114.1 (5)
C4—C5—C6	121.5 (5)	O3—C13—O4	124.8 (5)
C4—C5—H5	119.2	O3—C13—C14	120.4 (5)
C6—C5—H5	119.2	O4—C13—C14	114.6 (5)
C1—C6—C5	116.3 (5)	O2—C14—C15	110.3 (4)
C1—C6—C7	122.6 (5)	O2—C14—C13	110.9 (4)
C5—C6—C7	120.6 (5)	C15—C14—C13	110.3 (5)
N1—C7—C6	108.6 (4)	O2—C14—H14	108.4
N1—C7—C12	107.1 (4)	C15—C14—H14	108.4
C6—C7—C12	115.7 (4)	C13—C14—H14	108.4
N1—C7—C8	108.2 (4)	O5—C15—C14	107.9 (4)
C6—C7—C8	113.6 (4)	O5—C15—C16	112.2 (4)
C12—C7—C8	103.2 (4)	C14—C15—C16	114.3 (4)
C9—C8—C7	111.5 (4)	O5—C15—H15	107.4
C9—C8—H8A	109.3	C14—C15—H15	107.4
C7—C8—H8A	109.3	C16—C15—H15	107.4
C9—C8—H8B	109.3	O7—C16—O6	126.1 (5)
C7—C8—H8B	109.3	O7—C16—C15	118.3 (5)
H8A—C8—H8B	108.0	O6—C16—C15	115.6 (5)
C10—C9—C8	111.1 (5)	C14—O2—H2A	109.5
C10—C9—H9A	109.4	C15—O5—H5A	109.5
C8—C9—H9A	109.4	C16—O6—H6	109.5
C6—C1—C2—C3	1.5 (10)	C9—C10—C11—C12	55.6 (7)
Cl1—C1—C2—C3	−179.4 (5)	C10—C11—C12—O1	107.0 (6)
C1—C2—C3—C4	−2.1 (10)	C10—C11—C12—C7	−61.8 (6)
C2—C3—C4—C5	2.2 (9)	N1—C7—C12—O1	6.8 (6)
C3—C4—C5—C6	−1.8 (8)	C6—C7—C12—O1	128.1 (5)
C2—C1—C6—C5	−1.0 (8)	C8—C7—C12—O1	−107.2 (5)
Cl1—C1—C6—C5	179.9 (4)	N1—C7—C12—C11	175.9 (5)
C2—C1—C6—C7	−173.0 (5)	C6—C7—C12—C11	−62.8 (6)
Cl1—C1—C6—C7	7.9 (7)	C8—C7—C12—C11	61.9 (6)
C4—C5—C6—C1	1.2 (8)	O3—C13—C14—O2	−9.2 (7)
C4—C5—C6—C7	173.3 (5)	O4—C13—C14—O2	175.6 (4)
C1—C6—C7—N1	75.1 (6)	O3—C13—C14—C15	113.3 (5)
C5—C6—C7—N1	−96.5 (5)	O4—C13—C14—C15	−61.9 (6)
C1—C6—C7—C12	−45.3 (7)	O2—C14—C15—O5	65.8 (5)
C5—C6—C7—C12	143.0 (5)	C13—C14—C15—O5	−57.0 (6)
C1—C6—C7—C8	−164.5 (5)	O2—C14—C15—C16	−59.7 (6)
C5—C6—C7—C8	23.9 (6)	C13—C14—C15—C16	177.5 (5)
N1—C7—C8—C9	−172.2 (4)	O5—C15—C16—O7	9.9 (7)
C6—C7—C8—C9	67.1 (6)	C14—C15—C16—O7	133.1 (5)
C12—C7—C8—C9	−59.0 (5)	O5—C15—C16—O6	−170.8 (4)
C7—C8—C9—C10	59.8 (6)	C14—C15—C16—O6	−47.6 (6)
C8—C9—C10—C11	−56.0 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7i	0.91	1.81	2.715 (5)	176
N1—H1B···O4	0.91	2.05	2.856 (5)	147
N1—H1C···O1	0.91	2.13	2.642 (5)	115
N1—H1C···O3ii	0.91	2.29	2.893 (5)	123
N1—H1C···O5ii	0.91	2.37	3.001 (5)	126
O2—H2A···O3	0.84	2.24	2.672 (5)	112
O2—H2A···O1iii	0.84	2.60	3.388 (5)	157
O5—H5A···O6iv	0.84	2.09	2.864 (5)	153
O6—H6···O4v	0.84	1.64	2.460 (5)	166
O6—H6···O3v	0.84	2.62	3.265 (5)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O7i	0.91	1.81	2.715 (5)	176
N1—H1B⋯O4	0.91	2.05	2.856 (5)	147
N1—H1C⋯O3ii	0.91	2.29	2.893 (5)	123
N1—H1C⋯O5ii	0.91	2.37	3.001 (5)	126
O2—H2A⋯O1iii	0.84	2.60	3.388 (5)	157
O5—H5A⋯O6iv	0.84	2.09	2.864 (5)	153
O6—H6⋯O4v	0.84	1.64	2.460 (5)	166
O6—H6⋯O3v	0.84	2.62	3.265 (5)	134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .