N-[2-(2-Chloro-phen-yl)-2-hydroxy-ethyl]propan-2-aminium nitrate.

In the title compound, C(11)H(17)ClNO(+)·NO(3) (-), the side chain of the ethyl-ammonium group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethyl-ammonium group and the benzene ring being 79.40 (18)°. In the crystal structure, inter-molecular 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 = 276.72

Monoclinic,

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[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 ▶); 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 ▶).

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

C11H17ClNO+·NO3−	F(000) = 584
Mr = 276.72	Dx = 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

Rigaku R-AXIS RAPID diffractometer	3179 independent reflections
Radiation source: rolling anode	1833 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.900, Tmax = 0.940	l = −15→15
13380 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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.8267P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3179 reflections	Δρmax = 0.37 e Å−3
167 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .