[2-Acet-oxy-3-(naphthalen-1-yl-oxy)prop-yl](propan-2-yl)aza-nium chloride monohydrate.

The title compound, C18H24NO3 (+)·Cl(-)·H2O, was synthesized by the reaction of propranolol hydro-chloride with acetyl chloride in chloro-form 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 intra-molecular 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 = 355.85

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.200

S = 0.99

3424 reflections

219 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.28 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005515/bq2383sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005515/bq2383Isup3.cml

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

C18H24NO3+·Cl−·H2O	F(000) = 760
Mr = 355.85	Dx = 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

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

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(Fo2) + (0.1097P)2] where P = (Fo2 + 2Fc2)/3
3424 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.60 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

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
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*

	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)

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)

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

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⋯O1W i	0.96	2.53	3.469 (9)	166

Symmetry code: (i) .