[2-Acet­oxy-3-(naphthalen-1-yl­oxy)prop­yl](propan-2-yl)aza­nium chloride monohydrate

Liu, Y.-Y.; Xu, G.-H.; Li, Z.-J.; Xu, H.-Y.; Gu, C.-Q.

doi:10.1107/S1600536813005515

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o512

doi:10.1107/S1600536813005515

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[2-Acetoxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)azanium chloride monohydrate

Yuan-Yuan Liu,^a ^* Guang-Hui Xu,^a Zheng-Jie Li,^a Hong-Yu Xu ^a and Chang-Qing Gu ^a

^aDepartment of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, People's Republic of China
^*Correspondence e-mail: liuyuanyuan1985419@163.com

(Received 16 February 2013; accepted 26 February 2013; online 9 March 2013)

The title compound, C₁₈H₂₄NO₃⁺·Cl⁻·H₂O, was synthesized by the reaction of propranolol hydrochloride with acetyl chloride in chloroform followed by slow evaporation in air. In the cation, the dihedral angle between the planes of the naphthalene ring system and the acetate group is 71.1 (2)°. An intramolecular N—H⋯O hydrogen bond results in the formation of a non-planar pseudo-ring, with the ether O and the H atom displaced by −1.328 (2) and 0.65 Å, respectively, from the plane of the other ring atoms. The cation and anion are linked by an N—H⋯Cl hydrogen bond. The water molecule is linked to a methyl H atom by C—H⋯O hydrogen bond.

Related literature

The applications of the title compound, see: Barbosa et al. (2010 ). For the synthetic procedure, see: Irwin & Belaid (1987 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₂₄NO₃⁺·Cl⁻·H₂O
M_r = 355.85
Monoclinic, P 2₁ /c
a = 15.559 (3) Å
b = 8.2120 (16) Å
c = 14.665 (3) Å
β = 93.23 (3)°
V = 1870.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.936, T_max = 0.978
3424 measured reflections
3424 independent reflections
1948 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.200
S = 0.99
3424 reflections
219 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Cl	0.90	2.37	3.194 (3)	152
N—H0A⋯O2	0.90	2.59	2.948 (3)	105
C15—H15B⋯O1Wⁱ	0.96	2.53	3.469 (9)	166
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813005515/bq2383sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005515/bq2383Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005515/bq2383Isup3.cml

checkCIF report

Comment top

Propranolol hydrochloride is an important beta-adrenergic blocking agent, and used in the treatment of hypertension and cardiovascular disorders. Molecular modifications of propranolol are varied with examples in the amino-substituent, side-chain variants and nuclear changes including all mono ring-hydroxylated products (Irwin et al., 1987). Here, the title compound, (I), an important propranolol derivative, was synthesized by the reaction of propranolol hydrochloride with acetyl chloride in chloroform, and we report the crystal structure of (I).

In the molecule of (I), (Fig.1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angle of naphthalene ring system and acetate group is 71.11 °. The amino hydrogen is linked to chloride and oxygen atoms by the intramolecular N—H···Cl and N—H···O hydrogen bonds, respectively, which seem to be very effective in the stabilization of the crystal structure. The intramolecular N—H···O hydrogen bond results in the formation of one non-planar pseudo ring (O2/C12/C13/N/H0A), with O2 and H0A atoms displaced by -1.328 Å and 0.65 Å, respectively, from the plane of the other ring atoms.

Related literature top

The title compound is an important propranolol derivative. For background to its applications, see: Barbosa et al. (2010). For the synthetic procedure, see: Irwin & Belaid (1987). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by the literature method (Irwin et al., 1987). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in methanol (20 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown by dashed lines.

[2-Acetoxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)azanium chloride monohydrate top

Crystal data top

C₁₈H₂₄NO₃⁺·Cl⁻·H₂O	F(000) = 760
M_r = 355.85	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 15.559 (3) Å	θ = 9–13°
b = 8.2120 (16) Å	µ = 0.23 mm⁻¹
c = 14.665 (3) Å	T = 293 K
β = 93.23 (3)°	Block, yellow
V = 1870.8 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1948 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.4°, θ_min = 1.3°
ω/2θ scans	h = −18→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
T_min = 0.936, T_max = 0.978	l = 0→17
3424 measured reflections	3 standard reflections every 200 reflections
3424 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.200	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.1097P)²] where P = (F_o² + 2F_c²)/3
3424 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.60 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₂₄NO₃⁺·Cl⁻·H₂O	V = 1870.8 (6) Å³
M_r = 355.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.559 (3) Å	µ = 0.23 mm⁻¹
b = 8.2120 (16) Å	T = 293 K
c = 14.665 (3) Å	0.30 × 0.20 × 0.10 mm
β = 93.23 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1948 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.936, T_max = 0.978	3 standard reflections every 200 reflections
3424 measured reflections	intensity decay: 1%
3424 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	1 restraint
wR(F²) = 0.200	H-atom parameters constrained
S = 0.99	Δρ_max = 0.60 e Å⁻³
3424 reflections	Δρ_min = −0.28 e Å⁻³
219 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
N	0.40172 (17)	0.4306 (4)	0.60092 (17)	0.0541 (7)
H0A	0.3855	0.5068	0.5593	0.065*
H0B	0.4541	0.3943	0.5874	0.065*
O1	0.20414 (15)	0.0867 (3)	0.54378 (16)	0.0606 (7)
C1	0.0783 (2)	−0.0245 (5)	0.5948 (2)	0.0591 (10)
O2	0.27260 (14)	0.3625 (3)	0.45087 (15)	0.0553 (6)
C2	0.0499 (2)	0.1326 (6)	0.6206 (2)	0.0669 (11)
H2A	0.0842	0.2231	0.6110	0.080*
O3	0.3081 (2)	0.2709 (4)	0.31387 (19)	0.0930 (10)
C3	−0.0272 (3)	0.1522 (7)	0.6592 (3)	0.0810 (13)
H3A	−0.0450	0.2555	0.6758	0.097*
C4	−0.0788 (3)	0.0189 (9)	0.6735 (3)	0.0974 (17)
H4A	−0.1314	0.0343	0.6993	0.117*
C5	−0.0547 (3)	−0.1334 (8)	0.6510 (3)	0.0886 (15)
H5A	−0.0908	−0.2206	0.6619	0.106*
C6	0.0248 (3)	−0.1623 (6)	0.6110 (3)	0.0714 (12)
C7	0.0532 (3)	−0.3184 (6)	0.5867 (3)	0.0811 (13)
H7A	0.0194	−0.4091	0.5972	0.097*
C8	0.1295 (3)	−0.3368 (6)	0.5482 (3)	0.0821 (13)
H8A	0.1473	−0.4406	0.5322	0.099*
C9	0.1817 (3)	−0.2049 (5)	0.5320 (3)	0.0652 (10)
H9A	0.2338	−0.2211	0.5052	0.078*
C10	0.1576 (2)	−0.0522 (5)	0.5546 (2)	0.0538 (9)
C11	0.2810 (2)	0.0738 (5)	0.4924 (3)	0.0592 (9)
H11A	0.2657	0.0439	0.4296	0.071*
H11B	0.3192	−0.0088	0.5191	0.071*
C12	0.3240 (2)	0.2361 (4)	0.4961 (2)	0.0537 (9)
H12A	0.3791	0.2280	0.4672	0.064*
C13	0.3402 (2)	0.2938 (5)	0.5934 (2)	0.0582 (9)
H13A	0.2861	0.3276	0.6172	0.070*
H13B	0.3626	0.2039	0.6305	0.070*
C14	0.4085 (2)	0.5085 (5)	0.6944 (2)	0.0603 (10)
H14A	0.4113	0.4211	0.7400	0.072*
C15	0.4901 (3)	0.6048 (6)	0.7055 (3)	0.1012 (17)
H15A	0.4967	0.6463	0.7666	0.152*
H15B	0.4879	0.6939	0.6630	0.152*
H15C	0.5381	0.5359	0.6938	0.152*
C16	0.3301 (3)	0.6086 (6)	0.7096 (3)	0.0930 (15)
H16A	0.3348	0.6548	0.7698	0.140*
H16B	0.2798	0.5409	0.7035	0.140*
H16C	0.3255	0.6945	0.6652	0.140*
C17	0.2726 (2)	0.3674 (5)	0.3586 (2)	0.0626 (10)
C18	0.2213 (3)	0.5119 (6)	0.3213 (3)	0.0890 (14)
H18A	0.2218	0.5128	0.2559	0.134*
H18B	0.2465	0.6108	0.3453	0.134*
H18C	0.1630	0.5037	0.3391	0.134*
Cl	0.41641 (6)	0.70545 (13)	0.44852 (7)	0.0688 (4)
O1W	0.5140 (4)	0.0297 (9)	0.4132 (5)	0.252 (3)
H1WB	0.5328	−0.0674	0.4172	0.302*
H1WA	0.5574	0.0922	0.4113	0.302*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0495 (16)	0.0682 (19)	0.0441 (15)	−0.0011 (15)	−0.0008 (12)	−0.0002 (14)
O1	0.0526 (14)	0.0639 (16)	0.0663 (16)	−0.0022 (13)	0.0111 (12)	−0.0077 (13)
C1	0.050 (2)	0.085 (3)	0.0401 (18)	0.002 (2)	−0.0130 (16)	0.0034 (18)
O2	0.0534 (14)	0.0682 (16)	0.0438 (13)	0.0015 (12)	−0.0022 (10)	−0.0029 (11)
C2	0.054 (2)	0.090 (3)	0.056 (2)	0.002 (2)	−0.0078 (17)	−0.008 (2)
O3	0.110 (3)	0.121 (3)	0.0496 (16)	0.022 (2)	0.0121 (16)	−0.0121 (17)
C3	0.056 (3)	0.122 (4)	0.064 (3)	0.021 (3)	−0.004 (2)	−0.008 (3)
C4	0.058 (3)	0.165 (6)	0.069 (3)	0.010 (4)	0.007 (2)	0.010 (3)
C5	0.056 (3)	0.138 (5)	0.071 (3)	−0.019 (3)	−0.004 (2)	0.019 (3)
C6	0.053 (2)	0.106 (4)	0.054 (2)	−0.012 (2)	−0.0072 (17)	0.018 (2)
C7	0.086 (3)	0.082 (3)	0.074 (3)	−0.021 (3)	−0.010 (2)	0.018 (2)
C8	0.089 (3)	0.074 (3)	0.082 (3)	−0.001 (3)	−0.008 (3)	0.008 (2)
C9	0.061 (2)	0.072 (3)	0.061 (2)	−0.003 (2)	−0.0072 (18)	0.001 (2)
C10	0.0479 (19)	0.066 (3)	0.0473 (19)	−0.0038 (19)	−0.0015 (15)	−0.0021 (17)
C11	0.051 (2)	0.063 (2)	0.063 (2)	−0.0006 (18)	0.0019 (17)	−0.0068 (18)
C12	0.0424 (18)	0.066 (2)	0.053 (2)	0.0026 (17)	0.0037 (15)	0.0012 (17)
C13	0.059 (2)	0.067 (2)	0.049 (2)	−0.008 (2)	−0.0005 (16)	−0.0014 (18)
C14	0.064 (2)	0.076 (3)	0.0399 (18)	−0.002 (2)	−0.0031 (16)	−0.0029 (18)
C15	0.100 (4)	0.113 (4)	0.090 (3)	−0.035 (3)	0.004 (3)	−0.036 (3)
C16	0.090 (3)	0.108 (4)	0.079 (3)	0.028 (3)	−0.009 (2)	−0.027 (3)
C17	0.058 (2)	0.081 (3)	0.049 (2)	−0.016 (2)	−0.0001 (17)	0.001 (2)
C18	0.093 (3)	0.099 (3)	0.073 (3)	−0.012 (3)	−0.021 (2)	0.016 (3)
Cl	0.0648 (6)	0.0687 (7)	0.0732 (7)	0.0056 (5)	0.0059 (5)	0.0091 (5)
O1W	0.240 (7)	0.227 (7)	0.286 (8)	−0.022 (6)	−0.014 (7)	0.026 (6)

Geometric parameters (Å, º) top

N—C13	1.476 (4)	C9—C10	1.355 (5)
N—C14	1.511 (4)	C9—H9A	0.9300
N—H0A	0.9000	C11—C12	1.491 (5)
N—H0B	0.9000	C11—H11A	0.9700
O1—C10	1.365 (4)	C11—H11B	0.9700
O1—C11	1.452 (4)	C12—C13	1.511 (5)
C1—C10	1.416 (5)	C12—H12A	0.9800
C1—C2	1.422 (5)	C13—H13A	0.9700
C1—C6	1.432 (5)	C13—H13B	0.9700
O2—C17	1.353 (4)	C14—C15	1.498 (5)
O2—C12	1.448 (4)	C14—C16	1.498 (5)
C2—C3	1.364 (5)	C14—H14A	0.9800
C2—H2A	0.9300	C15—H15A	0.9600
O3—C17	1.186 (5)	C15—H15B	0.9600
C3—C4	1.380 (7)	C15—H15C	0.9600
C3—H3A	0.9300	C16—H16A	0.9600
C4—C5	1.352 (7)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.419 (6)	C17—C18	1.515 (6)
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.409 (6)	C18—H18B	0.9600
C7—C8	1.351 (6)	C18—H18C	0.9600
C7—H7A	0.9300	O1W—H1WB	0.8500
C8—C9	1.382 (6)	O1W—H1WA	0.8500
C8—H8A	0.9300

C13—N—C14	113.7 (3)	C12—C11—H11B	110.3
C13—N—H0A	108.8	H11A—C11—H11B	108.5
C14—N—H0A	108.8	O2—C12—C11	112.9 (3)
C13—N—H0B	108.8	O2—C12—C13	105.5 (3)
C14—N—H0B	108.8	C11—C12—C13	111.4 (3)
H0A—N—H0B	107.7	O2—C12—H12A	109.0
C10—O1—C11	117.2 (3)	C11—C12—H12A	109.0
C10—C1—C2	123.2 (4)	C13—C12—H12A	109.0
C10—C1—C6	118.1 (4)	N—C13—C12	112.5 (3)
C2—C1—C6	118.7 (4)	N—C13—H13A	109.1
C17—O2—C12	116.6 (3)	C12—C13—H13A	109.1
C3—C2—C1	120.7 (4)	N—C13—H13B	109.1
C3—C2—H2A	119.6	C12—C13—H13B	109.1
C1—C2—H2A	119.6	H13A—C13—H13B	107.8
C2—C3—C4	120.2 (5)	C15—C14—C16	112.7 (4)
C2—C3—H3A	119.9	C15—C14—N	109.7 (3)
C4—C3—H3A	119.9	C16—C14—N	110.6 (3)
C5—C4—C3	121.6 (5)	C15—C14—H14A	107.9
C5—C4—H4A	119.2	C16—C14—H14A	107.9
C3—C4—H4A	119.2	N—C14—H14A	107.9
C4—C5—C6	121.0 (5)	C14—C15—H15A	109.5
C4—C5—H5A	119.5	C14—C15—H15B	109.5
C6—C5—H5A	119.5	H15A—C15—H15B	109.5
C7—C6—C5	123.4 (5)	C14—C15—H15C	109.5
C7—C6—C1	118.9 (4)	H15A—C15—H15C	109.5
C5—C6—C1	117.7 (5)	H15B—C15—H15C	109.5
C8—C7—C6	120.2 (4)	C14—C16—H16A	109.5
C8—C7—H7A	119.9	C14—C16—H16B	109.5
C6—C7—H7A	119.9	H16A—C16—H16B	109.5
C7—C8—C9	121.5 (5)	C14—C16—H16C	109.5
C7—C8—H8A	119.3	H16A—C16—H16C	109.5
C9—C8—H8A	119.3	H16B—C16—H16C	109.5
C10—C9—C8	120.7 (4)	O3—C17—O2	124.0 (4)
C10—C9—H9A	119.7	O3—C17—C18	125.2 (4)
C8—C9—H9A	119.7	O2—C17—C18	110.8 (4)
C9—C10—O1	126.1 (3)	C17—C18—H18A	109.5
C9—C10—C1	120.7 (4)	C17—C18—H18B	109.5
O1—C10—C1	113.2 (3)	H18A—C18—H18B	109.5
O1—C11—C12	107.3 (3)	C17—C18—H18C	109.5
O1—C11—H11A	110.3	H18A—C18—H18C	109.5
C12—C11—H11A	110.3	H18B—C18—H18C	109.5
O1—C11—H11B	110.3	H1WB—O1W—H1WA	107.3

C10—C1—C2—C3	−179.9 (3)	C11—O1—C10—C1	−172.2 (3)
C6—C1—C2—C3	−0.6 (5)	C2—C1—C10—C9	179.6 (3)
C1—C2—C3—C4	−0.1 (6)	C6—C1—C10—C9	0.2 (5)
C2—C3—C4—C5	0.7 (7)	C2—C1—C10—O1	0.4 (5)
C3—C4—C5—C6	−0.4 (7)	C6—C1—C10—O1	−178.9 (3)
C4—C5—C6—C7	179.6 (4)	C10—O1—C11—C12	−175.7 (3)
C4—C5—C6—C1	−0.4 (6)	C17—O2—C12—C11	−78.9 (4)
C10—C1—C6—C7	0.2 (5)	C17—O2—C12—C13	159.2 (3)
C2—C1—C6—C7	−179.1 (3)	O1—C11—C12—O2	−64.4 (4)
C10—C1—C6—C5	−179.8 (3)	O1—C11—C12—C13	54.0 (4)
C2—C1—C6—C5	0.9 (5)	C14—N—C13—C12	170.7 (3)
C5—C6—C7—C8	179.5 (4)	O2—C12—C13—N	−72.0 (3)
C1—C6—C7—C8	−0.5 (6)	C11—C12—C13—N	165.1 (3)
C6—C7—C8—C9	0.3 (6)	C13—N—C14—C15	161.4 (4)
C7—C8—C9—C10	0.1 (6)	C13—N—C14—C16	−73.6 (4)
C8—C9—C10—O1	178.6 (3)	C12—O2—C17—O3	4.0 (5)
C8—C9—C10—C1	−0.4 (5)	C12—O2—C17—C18	−176.2 (3)
C11—O1—C10—C9	8.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Cl	0.90	2.37	3.194 (3)	152
N—H0A···O2	0.90	2.59	2.948 (3)	105
C15—H15B···O1Wⁱ	0.96	2.53	3.469 (9)	166

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄NO₃⁺·Cl⁻·H₂O
M_r	355.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.559 (3), 8.2120 (16), 14.665 (3)
β (°)	93.23 (3)
V (Å³)	1870.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.936, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	3424, 3424, 1948
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.200, 0.99
No. of reflections	3424
No. of parameters	219
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.28

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Cl	0.90	2.37	3.194 (3)	152
N—H0A···O2	0.90	2.59	2.948 (3)	105
C15—H15B···O1Wⁱ	0.9600	2.5300	3.469 (9)	166.00

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Barbosa, O., Ariza, C., Ortiz, C. & Torres, R. (2010). New Biotechnol. 27, 844–850. Web of Science CrossRef CAS Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Irwin, W. J. & Belaid, K. A. (1987). Drug Dev. Ind. Pharm. 13, 2017–2031. CrossRef CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 69| Part 4| April 2013| Page o512

doi:10.1107/S1600536813005515

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

[2-Acet­­oxy-3-(naphthalen-1-yl­­oxy)prop­yl](propan-2-yl)aza­nium chloride monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[2-Acetoxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)azanium chloride monohydrate