Crystal structure of [(2S,3R)-3-hy­droxy-3-phenyl­butan-2-yl]pyrrolidinium chloride

Kandhaswamy, A.; Meena, K.S.; Deepa, S.; Murugavel, S.

doi:10.1107/S2056989015016916

organic compounds

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Volume 71| Part 10| October 2015| Page o758

doi:10.1107/S2056989015016916

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Crystal structure of [(2S,3R)-3-hydroxy-3-phenylbutan-2-yl]pyrrolidinium chloride

Abirami Kandhaswamy,^a K.S. Meena,^a S. Deepa ^b and S. Murugavel ^c ^*

^aDepartment of Chemistry, Queen Mary's College, Chennai 600 004, Tamilnadu, India, ^bDepartment of Physics, Government College of Engineering, Salem 636 011, India, and ^cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
^*Correspondence e-mail: smurugavel27@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 4 September 2015; accepted 9 September 2015; online 17 September 2015)

In the title molecular salt, C₁₄H₂₂NO⁺·Cl⁻, the pyrrolidinium ring adopts a twisted conformation about one of the N—C bonds. It is oriented at a dihedral angle of 42.0 (1)° with respect to the benzene ring. The torsion angle for the central N—C—C—C_ar (ar = aromatic) linkage is 163.74 (15)°. In the crystal, the components are linked via N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming zigzig chains along the b-axis direction. These chains are connected along the c axis by very weak C—H⋯π interactions, forming a two-dimensional supramolecular network.

Keywords: crystal structure; salt; pyrrolidinium chloride; ionic liquids; hydrogen bonding.

CCDC reference: 1423292

1. Related literature

For background to pyrrolidinium-based ionic liquids, see: Henderson et al. (2006 ).

2. Experimental

2.1. Crystal data

C₁₄H₂₂NO⁺·Cl⁻
M_r = 255.78
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3912 (14) Å
b = 9.7002 (17) Å
c = 19.727 (4) Å
V = 1414.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.24 × 0.21 × 0.16 mm

2.2. Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.940, T_max = 0.960
6666 measured reflections
3163 independent reflections
2750 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.02
3163 reflections
160 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1235 Friedel pairs
Absolute structure parameter: −0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.89 (2)	2.24 (2)	3.0804 (19)	158.0 (2)
O1—H1A⋯Cl1ⁱⁱ	0.82	2.28	3.0456 (14)	156
C3—H3⋯Cgⁱⁱⁱ	0.93	2.93	3.630 (3)	133
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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 ).

Supporting information

CCDC reference: 1423292

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016916/hb7497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016916/hb7497Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016916/hb7497Isup3.cml

checkCIF report

Chemical context top

Pyrrolidinium-based ionic liquids have been a subject of intense investigation recently (Henderson et al., 2006), whereby with understanding of the fundamental molecular-level interactions, a desired product with predicted physico-chemical properites could be designed. Additionally, a particular emphasis has been placed on whether hydrogen bonding occurs between the cation and a potential electron-pair donor (hydrogen bond acceptor) and its influence on the ionic liquids' overall properties. Against this background, and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound (I) have been carried out.

Structural commentary top

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. In the cation, the pyrrolidinium ring adopts a twist conformation, with twist about the N1—C11 bond; the puckering parameters, q₂ = 0.361 (2) Å and φ₂ = 202.4 (5)°, and asymmetry parameters ΔC₂[N1—C11] = 4.8.0 (3) Å. The pyrrolidinium ring is oriented at an angle 42.0 (1)° from the mean plane of the benzene ring.

Supramolecular features top

In the crystal, cations and anions are linked via N1—H1···Cl1 and O1—H1A···Cl1 hydrogen bonds, forming a one-dimensional zig zig chain along the b-axis direction. These chains are stacked along the c-axis by C—H···π interactions, between benzene H atom and the benzene ring of an adjacene molecule, with a C3—H3···Cgⁱⁱⁱ, forming a two-dimensional supramolecular network. (Table 1 and Fig. 2; Cg is centroid of C1–C6 benzene ring. Symmetry code: (iii) -1/2+x,3/2-y,1-z>).

Synthesis and crystallization top

In a round bottomed flask, a stirred solution of (S)-pyrrolidinylnorephedrone was reacted with methylmagnesium bromide in THF medium over a period of 3 h. The completion of the reaction was monitored by thin layer chromatographic analysis. Further the crude mass was quenched with dil HCl and extracted with ethyl acetate under reduced vacuum. The resulting compound was recrystallised from EtOH/H₂O (4:1) solution as colourless blocks in good yield (86%).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. N-bound H atom was located in a difference Fourier map and freely refined. All other H atoms were positioned geometrically and constrained to ride on their parent atom with C—H = 0.93–0.97 Å and with U_iso(H)=1.5U_eq for methyl H atoms and 1.2U_eq(C) for other H atoms. Owing to poor agreement, the reflection (-3 2 4) was omitted from the final cycles of refinement.

Related literature top

For background to pyrrolidinium-based ionic liquids, see: Henderson et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 30% probability level.
	Fig. 2. Part of the crystal structure showing intermolecular N—H···Cl, O—H···Cl and C—H···π interactions, forming a two dimensional supramolecular network. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity. Cg is the centroid of C1–C6 benzene ring.

[(2S,3R)-3-Hydroxy-3-phenylbutan-2-yl]pyrrolidinium chloride top

Crystal data top

C₁₄H₂₂NO⁺·Cl⁻	F(000) = 552
M_r = 255.78	D_x = 1.201 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3836 reflections
a = 7.3912 (14) Å	θ = 3.7–29.2°
b = 9.7002 (17) Å	µ = 0.26 mm⁻¹
c = 19.727 (4) Å	T = 293 K
V = 1414.4 (4) Å³	Block, colourless
Z = 4	0.24 × 0.21 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 29.2°, θ_min = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.940, T_max = 0.960	k = −12→12
6666 measured reflections	l = −25→26

Refinement top

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0569P)² + 0.1443P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3163 reflections	Δρ_max = 0.19 e Å⁻³
160 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1235 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (7)

Crystal data top

C₁₄H₂₂NO⁺·Cl⁻	V = 1414.4 (4) Å³
M_r = 255.78	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3912 (14) Å	µ = 0.26 mm⁻¹
b = 9.7002 (17) Å	T = 293 K
c = 19.727 (4) Å	0.24 × 0.21 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3163 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2750 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.960	R_int = 0.024
6666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	Δρ_max = 0.19 e Å⁻³
S = 1.02	Δρ_min = −0.16 e Å⁻³
3163 reflections	Absolute structure: Flack (1983), 1235 Friedel pairs
160 parameters	Absolute structure parameter: −0.01 (7)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7420 (2)	0.74116 (19)	0.62918 (9)	0.0356 (4)
C2	0.6667 (3)	0.8068 (2)	0.57376 (10)	0.0478 (5)
H2	0.6323	0.8988	0.5772	0.057*
C3	0.6418 (4)	0.7369 (3)	0.51298 (12)	0.0596 (6)
H3	0.5911	0.7826	0.4762	0.071*
C4	0.6913 (4)	0.6009 (3)	0.50673 (12)	0.0623 (6)
H4	0.6728	0.5542	0.4661	0.075*
C5	0.7685 (3)	0.5345 (2)	0.56109 (13)	0.0568 (6)
H5	0.8043	0.4430	0.5570	0.068*
C6	0.7931 (3)	0.6034 (2)	0.62179 (11)	0.0440 (4)
H6	0.8446	0.5571	0.6583	0.053*
C7	0.7703 (2)	0.81613 (18)	0.69701 (9)	0.0345 (4)
C8	0.9719 (3)	0.8127 (3)	0.71443 (10)	0.0490 (5)
H8A	1.0408	0.8444	0.6762	0.074*
H8B	1.0069	0.7200	0.7253	0.074*
H8C	0.9946	0.8715	0.7527	0.074*
C9	0.6487 (3)	0.74346 (18)	0.75061 (9)	0.0333 (4)
H9	0.6670	0.6440	0.7451	0.040*
C10	0.4494 (3)	0.7716 (2)	0.73699 (10)	0.0461 (5)
H10A	0.3768	0.7182	0.7676	0.069*
H10B	0.4209	0.7464	0.6912	0.069*
H10C	0.4248	0.8678	0.7436	0.069*
C11	0.6819 (3)	0.9254 (2)	0.84700 (11)	0.0505 (5)
H11A	0.7778	0.9828	0.8289	0.061*
H11B	0.5659	0.9641	0.8341	0.061*
C12	0.6971 (4)	0.9122 (3)	0.92291 (12)	0.0723 (8)
H12A	0.8227	0.9160	0.9370	0.087*
H12B	0.6310	0.9855	0.9454	0.087*
C13	0.6170 (6)	0.7756 (3)	0.93918 (14)	0.0910 (11)
H13A	0.6936	0.7271	0.9712	0.109*
H13B	0.4988	0.7878	0.9597	0.109*
C14	0.6001 (3)	0.6945 (3)	0.87578 (10)	0.0612 (6)
H14A	0.4741	0.6830	0.8633	0.073*
H14B	0.6547	0.6041	0.8810	0.073*
N1	0.7001 (2)	0.77830 (17)	0.82284 (7)	0.0369 (4)
O1	0.7091 (2)	0.95487 (12)	0.69491 (7)	0.0457 (4)
H1A	0.7648	0.9970	0.6655	0.069*
Cl1	0.93476 (8)	0.17271 (6)	0.62270 (3)	0.05642 (18)
H1	0.817 (3)	0.761 (2)	0.8290 (9)	0.034 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0296 (9)	0.0393 (9)	0.0378 (9)	0.0004 (7)	0.0036 (7)	0.0035 (7)
C2	0.0494 (12)	0.0502 (12)	0.0439 (10)	0.0079 (10)	−0.0003 (9)	0.0068 (9)
C3	0.0524 (14)	0.0828 (16)	0.0434 (12)	0.0025 (13)	−0.0078 (10)	0.0065 (11)
C4	0.0620 (16)	0.0770 (16)	0.0479 (13)	−0.0072 (14)	0.0016 (11)	−0.0190 (11)
C5	0.0570 (15)	0.0475 (12)	0.0660 (15)	0.0006 (11)	0.0101 (11)	−0.0127 (10)
C6	0.0413 (10)	0.0425 (10)	0.0483 (11)	0.0046 (8)	0.0023 (9)	0.0038 (9)
C7	0.0318 (9)	0.0340 (8)	0.0378 (9)	0.0009 (8)	0.0036 (7)	0.0037 (7)
C8	0.0312 (10)	0.0675 (14)	0.0485 (11)	−0.0083 (10)	0.0034 (8)	0.0011 (10)
C9	0.0328 (9)	0.0311 (8)	0.0360 (9)	−0.0024 (7)	0.0002 (7)	0.0031 (7)
C10	0.0324 (10)	0.0557 (12)	0.0503 (11)	−0.0086 (9)	0.0016 (9)	0.0070 (9)
C11	0.0484 (13)	0.0465 (11)	0.0566 (12)	0.0007 (10)	0.0044 (10)	−0.0112 (9)
C12	0.0666 (17)	0.095 (2)	0.0550 (14)	0.0253 (16)	−0.0025 (13)	−0.0263 (14)
C13	0.133 (3)	0.092 (2)	0.0482 (14)	0.025 (2)	0.0297 (16)	0.0091 (13)
C14	0.0536 (14)	0.0890 (18)	0.0411 (11)	−0.0199 (12)	0.0026 (10)	0.0173 (12)
N1	0.0311 (9)	0.0417 (8)	0.0379 (8)	−0.0014 (7)	0.0042 (7)	0.0009 (6)
O1	0.0526 (9)	0.0307 (6)	0.0538 (8)	−0.0013 (6)	0.0164 (7)	0.0050 (6)
Cl1	0.0548 (3)	0.0642 (3)	0.0503 (3)	−0.0250 (3)	−0.0023 (3)	0.0119 (2)

Geometric parameters (Å, º) top

C1—C2	1.382 (3)	C9—H9	0.9800
C1—C6	1.396 (3)	C10—H10A	0.9600
C1—C7	1.537 (3)	C10—H10B	0.9600
C2—C3	1.390 (3)	C10—H10C	0.9600
C2—H2	0.9300	C11—C12	1.507 (3)
C3—C4	1.375 (4)	C11—N1	1.511 (3)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.375 (4)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.486 (4)
C5—C6	1.383 (3)	C12—H12A	0.9700
C5—H5	0.9300	C12—H12B	0.9700
C6—H6	0.9300	C13—C14	1.483 (4)
C7—O1	1.420 (2)	C13—H13A	0.9700
C7—C8	1.530 (3)	C13—H13B	0.9700
C7—C9	1.557 (2)	C14—N1	1.516 (3)
C8—H8A	0.9600	C14—H14A	0.9700
C8—H8B	0.9600	C14—H14B	0.9700
C8—H8C	0.9600	N1—H1	0.89 (2)
C9—N1	1.513 (2)	O1—H1A	0.8200
C9—C10	1.522 (3)

C2—C1—C6	117.9 (2)	C9—C10—H10B	109.5
C2—C1—C7	121.70 (17)	H10A—C10—H10B	109.5
C6—C1—C7	120.44 (18)	C9—C10—H10C	109.5
C1—C2—C3	120.7 (2)	H10A—C10—H10C	109.5
C1—C2—H2	119.6	H10B—C10—H10C	109.5
C3—C2—H2	119.6	C12—C11—N1	103.1 (2)
C4—C3—C2	120.7 (2)	C12—C11—H11A	111.2
C4—C3—H3	119.6	N1—C11—H11A	111.2
C2—C3—H3	119.6	C12—C11—H11B	111.2
C3—C4—C5	119.3 (2)	N1—C11—H11B	111.2
C3—C4—H4	120.3	H11A—C11—H11B	109.1
C5—C4—H4	120.3	C13—C12—C11	105.1 (2)
C4—C5—C6	120.3 (2)	C13—C12—H12A	110.7
C4—C5—H5	119.9	C11—C12—H12A	110.7
C6—C5—H5	119.9	C13—C12—H12B	110.7
C5—C6—C1	121.1 (2)	C11—C12—H12B	110.7
C5—C6—H6	119.4	H12A—C12—H12B	108.8
C1—C6—H6	119.4	C14—C13—C12	108.9 (2)
O1—C7—C8	109.73 (17)	C14—C13—H13A	109.9
O1—C7—C1	112.29 (15)	C12—C13—H13A	109.9
C8—C7—C1	108.54 (16)	C14—C13—H13B	109.9
O1—C7—C9	105.37 (14)	C12—C13—H13B	109.9
C8—C7—C9	113.58 (16)	H13A—C13—H13B	108.3
C1—C7—C9	107.36 (15)	C13—C14—N1	104.8 (2)
C7—C8—H8A	109.5	C13—C14—H14A	110.8
C7—C8—H8B	109.5	N1—C14—H14A	110.8
H8A—C8—H8B	109.5	C13—C14—H14B	110.8
C7—C8—H8C	109.5	N1—C14—H14B	110.8
H8A—C8—H8C	109.5	H14A—C14—H14B	108.9
H8B—C8—H8C	109.5	C11—N1—C9	119.07 (15)
N1—C9—C10	111.66 (16)	C11—N1—C14	104.25 (17)
N1—C9—C7	113.19 (15)	C9—N1—C14	114.00 (15)
C10—C9—C7	110.96 (15)	C11—N1—H1	102.7 (13)
N1—C9—H9	106.9	C9—N1—H1	109.3 (12)
C10—C9—H9	106.9	C14—N1—H1	106.2 (13)
C7—C9—H9	106.9	C7—O1—H1A	109.5
C9—C10—H10A	109.5

C6—C1—C2—C3	0.5 (3)	C1—C7—C9—N1	163.74 (15)
C7—C1—C2—C3	−179.8 (2)	O1—C7—C9—C10	50.1 (2)
C1—C2—C3—C4	0.1 (4)	C8—C7—C9—C10	170.19 (18)
C2—C3—C4—C5	−0.9 (4)	C1—C7—C9—C10	−69.8 (2)
C3—C4—C5—C6	1.1 (4)	N1—C11—C12—C13	−32.0 (3)
C4—C5—C6—C1	−0.5 (3)	C11—C12—C13—C14	14.7 (3)
C2—C1—C6—C5	−0.3 (3)	C12—C13—C14—N1	8.7 (3)
C7—C1—C6—C5	180.00 (19)	C12—C11—N1—C9	165.87 (19)
C2—C1—C7—O1	0.7 (2)	C12—C11—N1—C14	37.5 (2)
C6—C1—C7—O1	−179.62 (17)	C10—C9—N1—C11	−62.2 (2)
C2—C1—C7—C8	−120.8 (2)	C7—C9—N1—C11	63.9 (2)
C6—C1—C7—C8	58.9 (2)	C10—C9—N1—C14	61.6 (2)
C2—C1—C7—C9	116.06 (19)	C7—C9—N1—C14	−172.33 (17)
C6—C1—C7—C9	−64.3 (2)	C13—C14—N1—C11	−28.6 (3)
O1—C7—C9—N1	−76.39 (18)	C13—C14—N1—C9	−160.0 (2)
C8—C7—C9—N1	43.7 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.89 (2)	2.24 (2)	3.0804 (19)	158.0 (2)
O1—H1A···Cl1ⁱⁱ	0.82	2.28	3.0456 (14)	156
C3—H3···Cgⁱⁱⁱ	0.93	2.93	3.630 (3)	133

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.89 (2)	2.24 (2)	3.0804 (19)	158.0 (2)
O1—H1A···Cl1ⁱⁱ	0.82	2.28	3.0456 (14)	156
C3—H3···Cgⁱⁱⁱ	0.93	2.93	3.630 (3)	133

Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) x, y+1, z; (iii) x−1/2, −y+3/2, −z+1.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Henderson, W. A., Young, V. G. Jr, Pearson, W., Passerini, S., De Long, H. C. & Trulove, P. C. (2006). J. Phys. Condens. Matter, 18, 10377–10390. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of [(2S,3R)-3-hy­dr­oxy-3-phenyl­butan-2-yl]pyrrolidinium chloride

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of [(2S,3R)-3-hydroxy-3-phenylbutan-2-yl]pyrrolidinium chloride