PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o391.
Published online 2010 January 16. doi:  10.1107/S1600536809054506
PMCID: PMC2979831

N-[2-(2-Chloro­phen­yl)-2-hydroxy­ethyl]propan-2-aminium nitrate

Abstract

In the title compound, C11H17ClNO+·NO3 , the side chain of the ethyl­ammonium group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethyl­ammonium group and the benzene ring being 79.40 (18)°. In the crystal structure, inter­molecular O—H(...)O and N—H(...)O hydrogen bonds are observed between the cation and the anion.

Related literature

For related structures, see: Tang, Xu, Zhang & Feng (2009 [triangle]); Tang, Xu, Zheng & Feng (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o391-scheme1.jpg

Experimental

Crystal data

  • C11H17ClNO+·NO3
  • M r = 276.72
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o391-efi1.jpg
  • a = 11.9551 (6) Å
  • b = 10.4563 (5) Å
  • c = 12.2968 (7) Å
  • β = 115.109 (1)°
  • V = 1391.91 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 296 K
  • 0.38 × 0.36 × 0.22 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.900, T max = 0.940
  • 13380 measured reflections
  • 3179 independent reflections
  • 1833 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.145
  • S = 1.00
  • 3179 reflections
  • 167 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054506/is2504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054506/is2504Isup2.hkl

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

supplementary crystallographic information

Comment

A recent study reports the structure of bis{N-[2-(2-chlorophenyl)-2-hydroxyethyl]propan-2-aminium} oxalate (Tang, Xu, Zhang & Feng, 2009), which was synthesized by oxalic acid and clorprenaline (Tang, Xu, Zheng & Feng, 2009). Here using nitric acid instead of oxalic acid and following a similar synthetic procedure yields the title compound, (I).

In the molecular structure (Fig. 1), the Cl atom and the phenyl plane is almost planar with a deviation of 0.0118 Å. The dihedral angle between the plane formed by C1/C2/C8 and the benzene plane is 81.23 (18)°, which shows that the two planes are almost perpendicular. O—H···O and N—H···O hydrogen bonds are found in the crystal structure.

Experimental

Racemic clorprenaline was prepared by clorprenaline hydrochloride purchased from ShangHai Shengxin Medicine & Chemical Co., Ltd. ShangHai, China. Clorprenaline hydrochloride and NaOH in a molar ratio of 1:1 were mixed and dissolved in a methanol-water solution (1:1 v/v). The precipitate formed was filtered off, washed with water and dried. It was used without further purification. Racemic clorprenaline (3.0 g, 0.014 mol) was dissolved in ethanol (30 ml), then nitric acid was added to give pH of about 2. The resulting solution was concentrated and colorless crystals of (I) were obtained within one day at ambient temperature.

Refinement

All H atoms were placed in calculated positions and allowed to ride on their parent atoms, with C—H = 0.93 (aromatic), 0.98 (methine), 0.97 (methylene), 0.96 Å (methyl), O—H = 0.82 Å and N—H = 0.90 Å, and with Uiso(H) = 1.2–1.5 times Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels, showing 40% probability displacement ellipsoids.

Crystal data

C11H17ClNO+·NO3F(000) = 584
Mr = 276.72Dx = 1.320 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7750 reflections
a = 11.9551 (6) Åθ = 3.1–27.4°
b = 10.4563 (5) ŵ = 0.28 mm1
c = 12.2968 (7) ÅT = 296 K
β = 115.109 (1)°Chunk, colorless
V = 1391.91 (12) Å30.38 × 0.36 × 0.22 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer3179 independent reflections
Radiation source: rolling anode1833 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.1°
ω scansh = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −13→13
Tmin = 0.900, Tmax = 0.940l = −15→15
13380 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.145w = 1/[σ2(Fo2) + (0.0508P)2 + 0.8267P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3179 reflectionsΔρmax = 0.37 e Å3
167 parametersΔρmin = −0.49 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (2)

Special details

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.

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

xyzUiso*/Ueq
Cl10.50104 (7)0.95849 (7)0.13939 (6)0.1022 (3)
N20.28600 (14)0.45390 (15)0.33777 (14)0.0580 (4)
N10.37095 (12)0.76881 (13)0.40807 (13)0.0468 (4)
H2A0.37480.68320.41690.056*
H2B0.31280.78620.33390.056*
C80.49200 (14)0.81542 (17)0.41706 (16)0.0489 (4)
H8A0.55520.79900.49730.059*
H8B0.48770.90710.40390.059*
O10.53694 (12)0.61603 (12)0.34203 (12)0.0634 (4)
H1010.58120.59950.41260.095*
O20.28728 (13)0.33459 (13)0.33095 (13)0.0724 (5)
O30.23497 (15)0.52046 (14)0.24813 (13)0.0787 (5)
O40.33694 (14)0.50469 (14)0.43991 (12)0.0734 (4)
C90.33109 (16)0.82528 (19)0.49838 (17)0.0568 (5)
H80.33820.91860.49670.068*
C10.52762 (16)0.75053 (17)0.32594 (16)0.0521 (4)
H10.46150.76730.24610.063*
C20.64380 (17)0.81197 (18)0.33057 (17)0.0560 (5)
C70.6422 (2)0.9062 (2)0.25042 (18)0.0650 (5)
C30.75844 (18)0.7782 (2)0.4181 (2)0.0776 (7)
H30.76340.71550.47350.093*
C100.4135 (2)0.7788 (3)0.62253 (19)0.0801 (7)
H9A0.41500.68700.62320.096*
H9B0.38250.80890.67820.096*
H9C0.49570.81090.64550.096*
C60.7495 (2)0.9625 (2)0.2564 (2)0.0830 (6)
H60.74571.02430.20060.100*
C50.8610 (2)0.9267 (3)0.3447 (3)0.0923 (7)
H50.93330.96470.34960.111*
C110.19628 (19)0.7912 (3)0.4610 (2)0.0950 (9)
H10A0.14730.82550.38260.114*
H10B0.16900.82660.51760.114*
H10C0.18740.69990.45900.114*
C40.8659 (2)0.8349 (3)0.4258 (3)0.0942 (9)
H40.94160.81060.48610.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1190 (5)0.0985 (5)0.0691 (3)−0.0122 (4)0.0207 (3)0.0293 (3)
N20.0537 (8)0.0524 (9)0.0573 (9)−0.0069 (7)0.0134 (7)0.0004 (7)
N10.0444 (7)0.0437 (7)0.0513 (7)−0.0031 (6)0.0193 (6)−0.0005 (6)
C80.0448 (8)0.0489 (9)0.0546 (9)−0.0036 (7)0.0225 (7)−0.0004 (7)
O10.0721 (8)0.0509 (7)0.0686 (8)−0.0004 (6)0.0312 (6)−0.0032 (6)
O20.0794 (9)0.0485 (7)0.0677 (8)0.0020 (7)0.0105 (7)−0.0035 (6)
O30.0865 (10)0.0630 (8)0.0633 (8)−0.0017 (8)0.0093 (7)0.0125 (7)
O40.0934 (10)0.0564 (8)0.0567 (8)−0.0187 (7)0.0185 (7)−0.0061 (6)
C90.0538 (9)0.0598 (11)0.0636 (10)−0.0034 (8)0.0315 (8)−0.0127 (9)
C10.0557 (9)0.0533 (10)0.0497 (9)0.0023 (8)0.0247 (7)0.0062 (8)
C20.0629 (9)0.0551 (10)0.0619 (10)0.0007 (8)0.0378 (8)0.0024 (8)
C70.0842 (12)0.0617 (12)0.0610 (10)−0.0040 (10)0.0422 (9)−0.0010 (9)
C30.0563 (10)0.0833 (15)0.0978 (15)0.0062 (11)0.0371 (10)0.0233 (12)
C100.0859 (13)0.1027 (18)0.0609 (11)−0.0001 (13)0.0401 (10)−0.0077 (11)
C60.1148 (14)0.0703 (14)0.0984 (13)−0.0136 (13)0.0785 (11)−0.0028 (11)
C50.0847 (12)0.0848 (16)0.1380 (19)−0.0117 (13)0.0768 (13)−0.0115 (15)
C110.0604 (11)0.130 (2)0.1072 (17)−0.0126 (13)0.0480 (11)−0.0340 (16)
C40.0587 (11)0.1000 (19)0.132 (2)0.0021 (13)0.0478 (13)0.0155 (16)

Geometric parameters (Å, °)

Cl1—C71.748 (2)C1—H10.9800
N2—O31.225 (2)C2—C31.382 (3)
N2—O21.251 (2)C2—C71.388 (3)
N2—O41.258 (2)C7—C61.385 (3)
N1—C81.486 (2)C3—C41.381 (3)
N1—C91.503 (2)C3—H30.9300
N1—H2A0.9000C10—H9A0.9600
N1—H2B0.9000C10—H9B0.9600
C8—C11.517 (3)C10—H9C0.9600
C8—H8A0.9700C6—C51.366 (3)
C8—H8B0.9700C6—H60.9300
O1—C11.418 (2)C5—C41.368 (4)
O1—H1010.8200C5—H50.9300
C9—C101.504 (3)C11—H10A0.9600
C9—C111.519 (3)C11—H10B0.9600
C9—H80.9800C11—H10C0.9600
C1—C21.509 (3)C4—H40.9300
O3—N2—O2121.46 (16)C3—C2—C1120.90 (18)
O3—N2—O4120.26 (16)C7—C2—C1122.68 (17)
O2—N2—O4118.27 (16)C6—C7—C2122.1 (2)
C8—N1—C9114.86 (13)C6—C7—Cl1118.28 (17)
C8—N1—H2A108.6C2—C7—Cl1119.66 (16)
C9—N1—H2A108.6C4—C3—C2122.0 (2)
C8—N1—H2B108.6C4—C3—H3119.0
C9—N1—H2B108.6C2—C3—H3119.0
H2A—N1—H2B107.5C9—C10—H9A109.5
N1—C8—C1111.59 (14)C9—C10—H9B109.5
N1—C8—H8A109.3H9A—C10—H9B109.5
C1—C8—H8A109.3C9—C10—H9C109.5
N1—C8—H8B109.3H9A—C10—H9C109.5
C1—C8—H8B109.3H9B—C10—H9C109.5
H8A—C8—H8B108.0C5—C6—C7119.7 (2)
C1—O1—H101109.5C5—C6—H6120.2
N1—C9—C10110.28 (16)C7—C6—H6120.2
N1—C9—C11108.21 (16)C6—C5—C4119.8 (2)
C10—C9—C11112.7 (2)C6—C5—H5120.1
N1—C9—H8108.5C4—C5—H5120.1
C10—C9—H8108.5C9—C11—H10A109.5
C11—C9—H8108.5C9—C11—H10B109.5
O1—C1—C2113.60 (15)H10A—C11—H10B109.5
O1—C1—C8111.75 (15)C9—C11—H10C109.5
C2—C1—C8108.90 (15)H10A—C11—H10C109.5
O1—C1—H1107.4H10B—C11—H10C109.5
C2—C1—H1107.4C5—C4—C3120.0 (2)
C8—C1—H1107.4C5—C4—H4120.0
C3—C2—C7116.40 (19)C3—C4—H4120.0
C9—N1—C8—C1177.99 (14)C1—C2—C7—C6179.4 (2)
C8—N1—C9—C10−68.4 (2)C3—C2—C7—Cl1−178.09 (18)
C8—N1—C9—C11167.93 (18)C1—C2—C7—Cl10.5 (3)
N1—C8—C1—O1−59.77 (18)C7—C2—C3—C40.0 (4)
N1—C8—C1—C2173.93 (14)C1—C2—C3—C4−178.7 (2)
O1—C1—C2—C3−44.5 (3)C2—C7—C6—C5−1.1 (4)
C8—C1—C2—C380.7 (2)Cl1—C7—C6—C5177.8 (2)
O1—C1—C2—C7136.94 (19)C7—C6—C5—C40.6 (4)
C8—C1—C2—C7−97.8 (2)C6—C5—C4—C30.2 (4)
C3—C2—C7—C60.8 (3)C2—C3—C4—C5−0.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H2A···O40.901.972.843 (2)163
N1—H2B···O2i0.901.932.8234 (19)170
O1—H101···O4ii0.821.982.7614 (19)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2504).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2006). PROCESS-AUTO Rigaku/MSC. The Woodlands, Texas, USA.
  • Rigaku/MSC (2007). CrystalStructure Rigaku/MSC. The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tang, Z., Xu, M., Zhang, H.-C. & Feng, H. (2009). Acta Cryst. E65, o1670. [PMC free article] [PubMed]
  • Tang, Z., Xu, M., Zheng, G.-R. & Feng, H. (2009). Acta Cryst. E65, o1501. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography