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

Feng, H.; Tang, Z.; Xie, L.-J.; Xing, B.-T.

doi:10.1107/S1600536809054506

organic compounds

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Volume 66| Part 2| February 2010| Page o391

https://doi.org/10.1107/S1600536809054506

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

Hai Feng,^a ^* Zhan Tang,^a Lin-Jun Xie ^b and Bin-Tao Xing ^a

^aCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and ^bCollege of Mechanical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: fenghai289289@163.com

(Received 14 December 2009; accepted 17 December 2009; online 16 January 2010)

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 ); Tang, Xu, Zheng & Feng (2009 ).

Experimental

Crystal data

C₁₁H₁₇ClNO⁺·NO₃⁻
M_r = 276.72
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.145
S = 1.00
3179 reflections
167 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2A⋯O4	0.90	1.97	2.843 (2)	163
N1—H2B⋯O2ⁱ	0.90	1.93	2.8234 (19)	170
O1—H101⋯O4ⁱⁱ	0.82	1.98	2.7614 (19)	158
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ); 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054506/is2504Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2006); data reduction: CrystalStructure (Rigaku/MSC, 2007); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

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

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

Crystal data top

C₁₁H₁₇ClNO⁺·NO₃⁻	F(000) = 584
M_r = 276.72	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7750 reflections
a = 11.9551 (6) Å	θ = 3.1–27.4°
b = 10.4563 (5) Å	µ = 0.28 mm⁻¹
c = 12.2968 (7) Å	T = 296 K
β = 115.109 (1)°	Chunk, colorless
V = 1391.91 (12) Å³	0.38 × 0.36 × 0.22 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3179 independent reflections
Radiation source: rolling anode	1833 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.4°, θ_min = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
T_min = 0.900, T_max = 0.940	l = −15→15
13380 measured reflections

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0508P)² + 0.8267P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3179 reflections	Δρ_max = 0.37 e Å⁻³
167 parameters	Δρ_min = −0.49 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: 0.031 (2)

Crystal data top

C₁₁H₁₇ClNO⁺·NO₃⁻	V = 1391.91 (12) Å³
M_r = 276.72	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.9551 (6) Å	µ = 0.28 mm⁻¹
b = 10.4563 (5) Å	T = 296 K
c = 12.2968 (7) Å	0.38 × 0.36 × 0.22 mm
β = 115.109 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3179 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1833 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.940	R_int = 0.031
13380 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
3179 reflections	Δρ_min = −0.49 e Å⁻³
167 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
Cl1	0.50104 (7)	0.95849 (7)	0.13939 (6)	0.1022 (3)
N2	0.28600 (14)	0.45390 (15)	0.33777 (14)	0.0580 (4)
N1	0.37095 (12)	0.76881 (13)	0.40807 (13)	0.0468 (4)
H2A	0.3748	0.6832	0.4169	0.056*
H2B	0.3128	0.7862	0.3339	0.056*
C8	0.49200 (14)	0.81542 (17)	0.41706 (16)	0.0489 (4)
H8A	0.5552	0.7990	0.4973	0.059*
H8B	0.4877	0.9071	0.4039	0.059*
O1	0.53694 (12)	0.61603 (12)	0.34203 (12)	0.0634 (4)
H101	0.5812	0.5995	0.4126	0.095*
O2	0.28728 (13)	0.33459 (13)	0.33095 (13)	0.0724 (5)
O3	0.23497 (15)	0.52046 (14)	0.24813 (13)	0.0787 (5)
O4	0.33694 (14)	0.50469 (14)	0.43991 (12)	0.0734 (4)
C9	0.33109 (16)	0.82528 (19)	0.49838 (17)	0.0568 (5)
H8	0.3382	0.9186	0.4967	0.068*
C1	0.52762 (16)	0.75053 (17)	0.32594 (16)	0.0521 (4)
H1	0.4615	0.7673	0.2461	0.063*
C2	0.64380 (17)	0.81197 (18)	0.33057 (17)	0.0560 (5)
C7	0.6422 (2)	0.9062 (2)	0.25042 (18)	0.0650 (5)
C3	0.75844 (18)	0.7782 (2)	0.4181 (2)	0.0776 (7)
H3	0.7634	0.7155	0.4735	0.093*
C10	0.4135 (2)	0.7788 (3)	0.62253 (19)	0.0801 (7)
H9A	0.4150	0.6870	0.6232	0.096*
H9B	0.3825	0.8089	0.6782	0.096*
H9C	0.4957	0.8109	0.6455	0.096*
C6	0.7495 (2)	0.9625 (2)	0.2564 (2)	0.0830 (6)
H6	0.7457	1.0243	0.2006	0.100*
C5	0.8610 (2)	0.9267 (3)	0.3447 (3)	0.0923 (7)
H5	0.9333	0.9647	0.3496	0.111*
C11	0.19628 (19)	0.7912 (3)	0.4610 (2)	0.0950 (9)
H10A	0.1473	0.8255	0.3826	0.114*
H10B	0.1690	0.8266	0.5176	0.114*
H10C	0.1874	0.6999	0.4590	0.114*
C4	0.8659 (2)	0.8349 (3)	0.4258 (3)	0.0942 (9)
H4	0.9416	0.8106	0.4861	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1190 (5)	0.0985 (5)	0.0691 (3)	−0.0122 (4)	0.0207 (3)	0.0293 (3)
N2	0.0537 (8)	0.0524 (9)	0.0573 (9)	−0.0069 (7)	0.0134 (7)	0.0004 (7)
N1	0.0444 (7)	0.0437 (7)	0.0513 (7)	−0.0031 (6)	0.0193 (6)	−0.0005 (6)
C8	0.0448 (8)	0.0489 (9)	0.0546 (9)	−0.0036 (7)	0.0225 (7)	−0.0004 (7)
O1	0.0721 (8)	0.0509 (7)	0.0686 (8)	−0.0004 (6)	0.0312 (6)	−0.0032 (6)
O2	0.0794 (9)	0.0485 (7)	0.0677 (8)	0.0020 (7)	0.0105 (7)	−0.0035 (6)
O3	0.0865 (10)	0.0630 (8)	0.0633 (8)	−0.0017 (8)	0.0093 (7)	0.0125 (7)
O4	0.0934 (10)	0.0564 (8)	0.0567 (8)	−0.0187 (7)	0.0185 (7)	−0.0061 (6)
C9	0.0538 (9)	0.0598 (11)	0.0636 (10)	−0.0034 (8)	0.0315 (8)	−0.0127 (9)
C1	0.0557 (9)	0.0533 (10)	0.0497 (9)	0.0023 (8)	0.0247 (7)	0.0062 (8)
C2	0.0629 (9)	0.0551 (10)	0.0619 (10)	0.0007 (8)	0.0378 (8)	0.0024 (8)
C7	0.0842 (12)	0.0617 (12)	0.0610 (10)	−0.0040 (10)	0.0422 (9)	−0.0010 (9)
C3	0.0563 (10)	0.0833 (15)	0.0978 (15)	0.0062 (11)	0.0371 (10)	0.0233 (12)
C10	0.0859 (13)	0.1027 (18)	0.0609 (11)	−0.0001 (13)	0.0401 (10)	−0.0077 (11)
C6	0.1148 (14)	0.0703 (14)	0.0984 (13)	−0.0136 (13)	0.0785 (11)	−0.0028 (11)
C5	0.0847 (12)	0.0848 (16)	0.1380 (19)	−0.0117 (13)	0.0768 (13)	−0.0115 (15)
C11	0.0604 (11)	0.130 (2)	0.1072 (17)	−0.0126 (13)	0.0480 (11)	−0.0340 (16)
C4	0.0587 (11)	0.1000 (19)	0.132 (2)	0.0021 (13)	0.0478 (13)	0.0155 (16)

Geometric parameters (Å, º) top

Cl1—C7	1.748 (2)	C1—H1	0.9800
N2—O3	1.225 (2)	C2—C3	1.382 (3)
N2—O2	1.251 (2)	C2—C7	1.388 (3)
N2—O4	1.258 (2)	C7—C6	1.385 (3)
N1—C8	1.486 (2)	C3—C4	1.381 (3)
N1—C9	1.503 (2)	C3—H3	0.9300
N1—H2A	0.9000	C10—H9A	0.9600
N1—H2B	0.9000	C10—H9B	0.9600
C8—C1	1.517 (3)	C10—H9C	0.9600
C8—H8A	0.9700	C6—C5	1.366 (3)
C8—H8B	0.9700	C6—H6	0.9300
O1—C1	1.418 (2)	C5—C4	1.368 (4)
O1—H101	0.8200	C5—H5	0.9300
C9—C10	1.504 (3)	C11—H10A	0.9600
C9—C11	1.519 (3)	C11—H10B	0.9600
C9—H8	0.9800	C11—H10C	0.9600
C1—C2	1.509 (3)	C4—H4	0.9300

O3—N2—O2	121.46 (16)	C3—C2—C1	120.90 (18)
O3—N2—O4	120.26 (16)	C7—C2—C1	122.68 (17)
O2—N2—O4	118.27 (16)	C6—C7—C2	122.1 (2)
C8—N1—C9	114.86 (13)	C6—C7—Cl1	118.28 (17)
C8—N1—H2A	108.6	C2—C7—Cl1	119.66 (16)
C9—N1—H2A	108.6	C4—C3—C2	122.0 (2)
C8—N1—H2B	108.6	C4—C3—H3	119.0
C9—N1—H2B	108.6	C2—C3—H3	119.0
H2A—N1—H2B	107.5	C9—C10—H9A	109.5
N1—C8—C1	111.59 (14)	C9—C10—H9B	109.5
N1—C8—H8A	109.3	H9A—C10—H9B	109.5
C1—C8—H8A	109.3	C9—C10—H9C	109.5
N1—C8—H8B	109.3	H9A—C10—H9C	109.5
C1—C8—H8B	109.3	H9B—C10—H9C	109.5
H8A—C8—H8B	108.0	C5—C6—C7	119.7 (2)
C1—O1—H101	109.5	C5—C6—H6	120.2
N1—C9—C10	110.28 (16)	C7—C6—H6	120.2
N1—C9—C11	108.21 (16)	C6—C5—C4	119.8 (2)
C10—C9—C11	112.7 (2)	C6—C5—H5	120.1
N1—C9—H8	108.5	C4—C5—H5	120.1
C10—C9—H8	108.5	C9—C11—H10A	109.5
C11—C9—H8	108.5	C9—C11—H10B	109.5
O1—C1—C2	113.60 (15)	H10A—C11—H10B	109.5
O1—C1—C8	111.75 (15)	C9—C11—H10C	109.5
C2—C1—C8	108.90 (15)	H10A—C11—H10C	109.5
O1—C1—H1	107.4	H10B—C11—H10C	109.5
C2—C1—H1	107.4	C5—C4—C3	120.0 (2)
C8—C1—H1	107.4	C5—C4—H4	120.0
C3—C2—C7	116.40 (19)	C3—C4—H4	120.0

C9—N1—C8—C1	177.99 (14)	C1—C2—C7—C6	179.4 (2)
C8—N1—C9—C10	−68.4 (2)	C3—C2—C7—Cl1	−178.09 (18)
C8—N1—C9—C11	167.93 (18)	C1—C2—C7—Cl1	0.5 (3)
N1—C8—C1—O1	−59.77 (18)	C7—C2—C3—C4	0.0 (4)
N1—C8—C1—C2	173.93 (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—C3	80.7 (2)	Cl1—C7—C6—C5	177.8 (2)
O1—C1—C2—C7	136.94 (19)	C7—C6—C5—C4	0.6 (4)
C8—C1—C2—C7	−97.8 (2)	C6—C5—C4—C3	0.2 (4)
C3—C2—C7—C6	0.8 (3)	C2—C3—C4—C5	−0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2A···O4	0.90	1.97	2.843 (2)	163
N1—H2B···O2ⁱ	0.90	1.93	2.8234 (19)	170
O1—H101···O4ⁱⁱ	0.82	1.98	2.7614 (19)	158

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇ClNO⁺·NO₃⁻
M_r	276.72
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.9551 (6), 10.4563 (5), 12.2968 (7)
β (°)	115.109 (1)
V (Å³)	1391.91 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.38 × 0.36 × 0.22

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.900, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	13380, 3179, 1833
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.145, 1.00
No. of reflections	3179
No. of parameters	167
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.49

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2006), CrystalStructure (Rigaku/MSC, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2A···O4	0.90	1.97	2.843 (2)	163.0
N1—H2B···O2ⁱ	0.90	1.93	2.8234 (19)	169.6
O1—H101···O4ⁱⁱ	0.82	1.98	2.7614 (19)	158.4

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

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2006). PROCESS-AUTO. Rigaku/MSC. The Woodlands, Texas, USA. Google Scholar
Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC. The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, Z., Xu, M., Zhang, H.-C. & Feng, H. (2009). Acta Cryst. E65, o1670. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tang, Z., Xu, M., Zheng, G.-R. & Feng, H. (2009). Acta Cryst. E65, o1501. Web of Science CSD CrossRef IUCr Journals Google Scholar

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