1-[(Diethyl­amino­carbon­yl)meth­yl]-2-[hydr­oxy(6-methoxy­quinolin-4-yl)meth­yl]-5-vinyl-1-azoniabicyclo­[2.2.2]octane chloride monohydrate

Zhang, L.-P.; Wei, L.-J.; Chen, M.-Q.

doi:10.1107/S1600536807068444

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o518

doi:10.1107/S1600536807068444

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1-[(Diethylaminocarbonyl)methyl]-2-[hydroxy(6-methoxyquinolin-4-yl)methyl]-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride monohydrate

Li-Ping Zhang,^a ^* Lin-Juan Wei ^a and Ming-Qing Chen ^a

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi 214122, Jiangsu, People's Republic of China
^*Correspondence e-mail: zhangliping76518@163.com.cn

(Received 6 December 2007; accepted 27 December 2007; online 25 January 2008)

In the title compound, C₂₆H₃₆N₃O₃⁺·Cl⁻·H₂O, the molecular structure of the cation is stabilized by a number of C—H⋯O intramolecular interactions. In the crystal structure, O—H⋯Cl and C—H⋯Cl hydrogen bonds link the ions into a ribbon-like structure along the a axis.

Related literature

For related structures, see: Oleksyn et al. (1979 ); Zhang et al. (2006 ).

Experimental

Crystal data

C₂₆H₃₆N₃O₃⁺·Cl⁻·H₂O
M_r = 492.04
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.2213 (12) Å
b = 17.441 (3) Å
c = 18.161 (3) Å
V = 2604.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 292 K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.938, T_max = 0.973
15334 measured reflections
5361 independent reflections
3043 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.111
S = 0.99
5361 reflections
311 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), with 2317 Friedel pairs
Flack parameter: 0.14 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl1	0.82	2.25	3.038 (2)	161
C19—H19A⋯Cl1ⁱ	0.97	2.70	3.580 (4)	150
C20—H20B⋯O2	0.97	2.33	3.001 (4)	126
C21—H21B⋯Cl1	0.97	2.76	3.650 (3)	152
C21—H21B⋯O2	0.97	2.58	3.169 (4)	119
O4⋯Cl1ⁱⁱ			3.141 (4)
O4⋯Cl1ⁱⁱⁱ			3.214 (4)
Symmetry codes: (i) x+1, y, z; (ii) 1+x, y, -1+z; (iii) $[{1 \over 2}+x, {3 \over 2}-y, 1-z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068444/ci2541sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068444/ci2541Isup2.hkl

checkCIF report

Comment top

In the title compound (Fig. 1), the quinoline ring system is planar with a maximum deviation of 0.026 (3) Å for atom C8. Bond lengths and angles are comparable to those observed in a related cinchonine structure (Oleksyn et al., 1979) but the molecules differ slightly in the relative orientations of azoniabicyclo[2.2.2]octane and quinoline units.

The structure of cation is stabilized by a number of C—H···O intramolecular interactions. In the crystal structure O—H···Cl, C—H···Cl and O_w···Cl interactions link the ions into a ribbon along the a axis (Fig.2). Similar packing arrangement is found in the structure of a related cinchonine quaternary salt (Zhang et al., 2006).

Related literature top

For related structures, see: Oleksyn et al. (1979); Zhang et al. (2006).

Experimental top

The title compound was prepared by the reaction of 2-chloro-N,N-diethylacetamide (3 mmol) with quinine (2 mmol) in acetone (5 ml) refluxed for 5 h under a N₂ atmosphere. The resulting precipitate was isolated by filtration, washed, dried, and recrystallized from Et₂O and CH₂Cl₂ (7:1). Single crystals suitable for X-ray diffraction study were obtained from CH₂Cl₂ by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. Water molecule has been omitted for clarity.
	Fig. 2. The molecular packing of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonding have been omitted.

1-[(Diethylaminocarbonyl)methyl]-2-[hydroxy(6-methoxyquinolin-4-yl)methyl]- 5-vinyl-1-azoniabicyclo[2.2.2]octane chloride monohydrate top

Crystal data top

C₂₆H₃₆N₃O₃⁺·Cl⁻·H₂O	F(000) = 1056
M_r = 492.04	D_x = 1.255 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2754 reflections
a = 8.2213 (12) Å	θ = 2.3–21.7°
b = 17.441 (3) Å	µ = 0.18 mm⁻¹
c = 18.161 (3) Å	T = 292 K
V = 2604.0 (7) Å³	Block, colourless
Z = 4	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5361 independent reflections
Radiation source: fine-focus sealed tube	3043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→10
T_min = 0.938, T_max = 0.973	k = −21→21
15334 measured reflections	l = −19→22

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0381P)² + 0.4431P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
5361 reflections	Δρ_max = 0.15 e Å⁻³
311 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2317 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (9)

Crystal data top

C₂₆H₃₆N₃O₃⁺·Cl⁻·H₂O	V = 2604.0 (7) Å³
M_r = 492.04	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.2213 (12) Å	µ = 0.18 mm⁻¹
b = 17.441 (3) Å	T = 292 K
c = 18.161 (3) Å	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5361 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3043 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.973	R_int = 0.062
15334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.111	Δρ_max = 0.15 e Å⁻³
S = 1.00	Δρ_min = −0.18 e Å⁻³
5361 reflections	Absolute structure: Flack (1983), 2317 Friedel pairs
311 parameters	Absolute structure parameter: 0.14 (9)
0 restraints

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
O1	0.3225 (4)	0.93582 (15)	0.56437 (14)	0.0753 (8)
O2	0.4216 (3)	0.66267 (12)	0.82251 (11)	0.0479 (6)
H2	0.3525	0.6737	0.8533	0.072*
O3	0.5222 (3)	0.90203 (12)	0.78329 (11)	0.0526 (6)
N2	0.6959 (3)	0.76896 (13)	0.82281 (11)	0.0354 (6)
N3	0.4329 (4)	0.92548 (14)	0.89798 (14)	0.0464 (7)
C1	0.3147 (4)	0.73809 (18)	0.63577 (14)	0.0376 (7)
C2	0.3419 (4)	0.81809 (18)	0.63353 (16)	0.0410 (8)
H2A	0.3878	0.8426	0.6739	0.049*
C3	0.3012 (5)	0.8596 (2)	0.57254 (18)	0.0539 (9)
C4	0.2293 (5)	0.8234 (2)	0.51162 (18)	0.0663 (12)
H4	0.2016	0.8523	0.4705	0.080*
C5	0.2000 (5)	0.7482 (3)	0.51186 (17)	0.0637 (10)
H5	0.1515	0.7254	0.4711	0.076*
C6	0.2417 (4)	0.7029 (2)	0.57315 (17)	0.0470 (9)
N1	0.2080 (4)	0.62659 (18)	0.56833 (16)	0.0588 (8)
C7	0.2426 (4)	0.5857 (2)	0.6256 (2)	0.0548 (10)
H7	0.2206	0.5335	0.6232	0.066*
C8	0.3111 (4)	0.61412 (19)	0.69128 (17)	0.0474 (8)
H8	0.3299	0.5814	0.7308	0.057*
C9	0.3497 (4)	0.69032 (18)	0.69654 (15)	0.0363 (8)
C10	0.4145 (7)	0.9754 (2)	0.6174 (3)	0.1019 (17)
H10A	0.5159	0.9494	0.6250	0.153*
H10B	0.3552	0.9773	0.6629	0.153*
H10C	0.4351	1.0267	0.6005	0.153*
C11	0.4261 (4)	0.72014 (16)	0.76742 (14)	0.0328 (7)
H11	0.3644	0.7648	0.7845	0.039*
C12	0.6021 (3)	0.74435 (18)	0.75294 (13)	0.0320 (7)
H12	0.5983	0.7890	0.7202	0.038*
C13	0.7026 (4)	0.68341 (19)	0.71416 (16)	0.0414 (8)
H13A	0.6918	0.6892	0.6613	0.050*
H13B	0.6632	0.6329	0.7276	0.050*
C14	0.8815 (4)	0.6912 (2)	0.73606 (18)	0.0486 (9)
H14	0.9506	0.6614	0.7027	0.058*
C15	0.9306 (4)	0.7755 (2)	0.73507 (17)	0.0527 (9)
H15	1.0470	0.7775	0.7466	0.063*
C16	0.8411 (4)	0.81627 (19)	0.79803 (16)	0.0440 (8)
H16A	0.9148	0.8237	0.8391	0.053*
H16B	0.8045	0.8663	0.7815	0.053*
C19	0.8954 (5)	0.6608 (2)	0.81431 (18)	0.0571 (10)
H19A	1.0031	0.6715	0.8336	0.069*
H19B	0.8793	0.6057	0.8146	0.069*
C20	0.7671 (4)	0.69938 (17)	0.86258 (16)	0.0464 (9)
H20A	0.8160	0.7155	0.9087	0.056*
H20B	0.6810	0.6631	0.8737	0.056*
C17	0.9092 (5)	0.8107 (3)	0.6606 (2)	0.0611 (11)
H17	0.9496	0.7822	0.6214	0.073*
C18	0.8428 (6)	0.8751 (3)	0.6433 (2)	0.0897 (15)
H18A	0.7999	0.9065	0.6799	0.108*
H18B	0.8377	0.8902	0.5943	0.108*
C21	0.5994 (4)	0.81309 (17)	0.87826 (14)	0.0370 (7)
H21A	0.6714	0.8280	0.9181	0.044*
H21B	0.5172	0.7794	0.8988	0.044*
C22	0.5158 (4)	0.88459 (17)	0.84909 (17)	0.0388 (8)
C23	0.3385 (5)	0.9913 (2)	0.8714 (2)	0.0639 (11)
H23A	0.3963	1.0152	0.8309	0.077*
H23B	0.3297	1.0288	0.9107	0.077*
C24	0.1710 (6)	0.9696 (3)	0.8462 (3)	0.116 (2)
H24A	0.1116	0.9479	0.8866	0.174*
H24B	0.1788	0.9327	0.8071	0.174*
H24C	0.1154	1.0145	0.8287	0.174*
C25	0.4319 (5)	0.9119 (2)	0.97795 (17)	0.0571 (10)
H25A	0.4590	0.8587	0.9874	0.069*
H25B	0.3233	0.9210	0.9968	0.069*
C26	0.5499 (6)	0.9624 (2)	1.0182 (2)	0.0776 (14)
H26A	0.5298	1.0150	1.0056	0.116*
H26B	0.6589	0.9489	1.0044	0.116*
H26C	0.5365	0.9556	1.0703	0.116*
Cl1	0.19903 (11)	0.74211 (6)	0.93207 (4)	0.0619 (3)
O4	0.9536 (5)	0.8684 (2)	−0.01438 (18)	0.1224 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.102 (2)	0.0584 (17)	0.0655 (16)	0.0077 (16)	−0.0188 (19)	0.0180 (14)
O2	0.0541 (17)	0.0496 (14)	0.0399 (12)	−0.0007 (12)	0.0049 (12)	0.0114 (11)
O3	0.0734 (18)	0.0461 (14)	0.0383 (13)	0.0105 (13)	0.0025 (13)	0.0030 (11)
N2	0.0321 (14)	0.0401 (15)	0.0341 (12)	0.0020 (13)	0.0009 (13)	−0.0032 (11)
N3	0.055 (2)	0.0343 (16)	0.0500 (16)	0.0071 (15)	0.0124 (15)	−0.0005 (12)
C1	0.0311 (17)	0.048 (2)	0.0341 (15)	0.0033 (17)	0.0008 (15)	−0.0072 (15)
C2	0.040 (2)	0.049 (2)	0.0342 (17)	0.0088 (17)	−0.0035 (16)	0.0010 (15)
C3	0.060 (2)	0.055 (2)	0.046 (2)	0.012 (2)	−0.001 (2)	0.0022 (18)
C4	0.082 (3)	0.078 (3)	0.0381 (19)	0.016 (3)	−0.009 (2)	0.005 (2)
C5	0.073 (3)	0.080 (3)	0.0382 (18)	0.009 (3)	−0.015 (2)	−0.009 (2)
C6	0.044 (2)	0.055 (2)	0.0419 (19)	0.0060 (17)	−0.0009 (17)	−0.0078 (17)
N1	0.0565 (19)	0.065 (2)	0.0547 (18)	0.0069 (17)	−0.0075 (18)	−0.0142 (17)
C7	0.045 (2)	0.050 (2)	0.069 (2)	−0.0047 (18)	−0.001 (2)	−0.020 (2)
C8	0.0370 (19)	0.051 (2)	0.054 (2)	−0.0063 (18)	0.0021 (18)	−0.0017 (16)
C9	0.0263 (18)	0.0421 (19)	0.0403 (17)	−0.0032 (15)	0.0043 (15)	−0.0049 (15)
C10	0.146 (5)	0.049 (3)	0.111 (4)	−0.002 (3)	−0.038 (4)	0.019 (3)
C11	0.0324 (18)	0.0349 (17)	0.0310 (15)	0.0007 (14)	0.0006 (14)	0.0008 (13)
C12	0.0288 (16)	0.0425 (18)	0.0247 (13)	0.0041 (15)	−0.0030 (13)	−0.0017 (13)
C13	0.0324 (18)	0.051 (2)	0.0407 (17)	0.0089 (18)	−0.0004 (17)	−0.0122 (15)
C14	0.032 (2)	0.062 (2)	0.051 (2)	0.0098 (18)	−0.0014 (17)	−0.0197 (18)
C15	0.0279 (19)	0.073 (3)	0.057 (2)	−0.0010 (19)	0.0005 (18)	−0.0126 (19)
C16	0.034 (2)	0.053 (2)	0.0451 (18)	−0.0070 (17)	−0.0019 (17)	−0.0046 (16)
C19	0.048 (2)	0.058 (2)	0.065 (2)	0.0162 (19)	−0.016 (2)	−0.0141 (19)
C20	0.052 (2)	0.044 (2)	0.0426 (18)	0.0094 (17)	−0.0153 (18)	−0.0010 (15)
C17	0.043 (2)	0.086 (3)	0.054 (2)	−0.013 (2)	0.014 (2)	−0.004 (2)
C18	0.110 (4)	0.095 (4)	0.064 (3)	−0.020 (3)	0.022 (3)	0.009 (3)
C21	0.0422 (19)	0.0399 (18)	0.0288 (14)	0.0031 (16)	−0.0018 (15)	−0.0058 (14)
C22	0.040 (2)	0.0332 (18)	0.0427 (19)	−0.0022 (16)	−0.0007 (16)	−0.0042 (15)
C23	0.075 (3)	0.040 (2)	0.077 (3)	0.020 (2)	0.010 (2)	0.0034 (19)
C24	0.057 (3)	0.106 (4)	0.186 (6)	0.015 (3)	0.008 (4)	0.059 (4)
C25	0.076 (3)	0.051 (2)	0.0440 (19)	0.003 (2)	0.023 (2)	−0.0046 (17)
C26	0.117 (4)	0.061 (3)	0.055 (2)	−0.019 (3)	−0.001 (3)	−0.0084 (19)
Cl1	0.0504 (5)	0.0839 (7)	0.0515 (5)	−0.0123 (5)	0.0083 (5)	−0.0087 (5)
O4	0.128 (3)	0.127 (3)	0.113 (2)	−0.002 (2)	0.014 (2)	−0.004 (2)

Geometric parameters (Å, º) top

O1—C3	1.349 (4)	C13—C14	1.529 (4)
O1—C10	1.406 (5)	C13—H13A	0.97
O2—C11	1.417 (3)	C13—H13B	0.97
O2—H2	0.82	C14—C19	1.521 (5)
O3—C22	1.234 (3)	C14—C15	1.525 (5)
N2—C21	1.495 (3)	C14—H14	0.98
N2—C16	1.519 (4)	C15—C17	1.496 (5)
N2—C20	1.529 (4)	C15—C16	1.535 (4)
N2—C12	1.546 (3)	C15—H15	0.98
N3—C22	1.327 (4)	C16—H16A	0.97
N3—C23	1.468 (4)	C16—H16B	0.97
N3—C25	1.472 (4)	C19—C20	1.528 (4)
C1—C9	1.412 (4)	C19—H19A	0.97
C1—C2	1.414 (4)	C19—H19B	0.97
C1—C6	1.425 (4)	C20—H20A	0.97
C2—C3	1.365 (4)	C20—H20B	0.97
C2—H2A	0.93	C17—C18	1.287 (5)
C3—C4	1.405 (5)	C17—H17	0.93
C4—C5	1.333 (5)	C18—H18A	0.93
C4—H4	0.93	C18—H18B	0.93
C5—C6	1.407 (5)	C21—C22	1.519 (4)
C5—H5	0.93	C21—H21A	0.97
C6—N1	1.363 (4)	C21—H21B	0.97
N1—C7	1.293 (4)	C23—C24	1.500 (6)
C7—C8	1.409 (4)	C23—H23A	0.97
C7—H7	0.93	C23—H23B	0.97
C8—C9	1.370 (4)	C24—H24A	0.96
C8—H8	0.93	C24—H24B	0.96
C9—C11	1.524 (4)	C24—H24C	0.96
C10—H10A	0.96	C25—C26	1.500 (5)
C10—H10B	0.96	C25—H25A	0.97
C10—H10C	0.96	C25—H25B	0.97
C11—C12	1.530 (4)	C26—H26A	0.96
C11—H11	0.98	C26—H26B	0.96
C12—C13	1.519 (4)	C26—H26C	0.96
C12—H12	0.98

C3—O1—C10	118.6 (3)	C19—C14—H14	110.5
C11—O2—H2	109.5	C15—C14—H14	110.5
C21—N2—C16	109.7 (2)	C13—C14—H14	110.5
C21—N2—C20	107.1 (2)	C17—C15—C14	112.1 (3)
C16—N2—C20	105.7 (2)	C17—C15—C16	115.2 (3)
C21—N2—C12	115.5 (2)	C14—C15—C16	108.2 (3)
C16—N2—C12	107.4 (2)	C17—C15—H15	107.0
C20—N2—C12	111.0 (2)	C14—C15—H15	107.0
C22—N3—C23	118.2 (3)	C16—C15—H15	107.0
C22—N3—C25	125.2 (3)	N2—C16—C15	110.2 (3)
C23—N3—C25	116.6 (3)	N2—C16—H16A	109.6
C9—C1—C2	124.9 (3)	C15—C16—H16A	109.6
C9—C1—C6	117.1 (3)	N2—C16—H16B	109.6
C2—C1—C6	117.9 (3)	C15—C16—H16B	109.6
C3—C2—C1	120.6 (3)	H16A—C16—H16B	108.1
C3—C2—H2A	119.7	C14—C19—C20	109.3 (3)
C1—C2—H2A	119.7	C14—C19—H19A	109.8
O1—C3—C2	125.5 (3)	C20—C19—H19A	109.8
O1—C3—C4	114.3 (3)	C14—C19—H19B	109.8
C2—C3—C4	120.2 (3)	C20—C19—H19B	109.8
C5—C4—C3	121.1 (3)	H19A—C19—H19B	108.3
C5—C4—H4	119.5	C19—C20—N2	110.0 (2)
C3—C4—H4	119.5	C19—C20—H20A	109.7
C4—C5—C6	120.7 (3)	N2—C20—H20A	109.7
C4—C5—H5	119.6	C19—C20—H20B	109.7
C6—C5—H5	119.6	N2—C20—H20B	109.7
N1—C6—C5	116.6 (3)	H20A—C20—H20B	108.2
N1—C6—C1	123.9 (3)	C18—C17—C15	129.0 (4)
C5—C6—C1	119.5 (3)	C18—C17—H17	115.5
C7—N1—C6	116.3 (3)	C15—C17—H17	115.5
N1—C7—C8	125.1 (3)	C17—C18—H18A	120.0
N1—C7—H7	117.5	C17—C18—H18B	120.0
C8—C7—H7	117.5	H18A—C18—H18B	120.0
C9—C8—C7	119.5 (3)	N2—C21—C22	115.3 (2)
C9—C8—H8	120.2	N2—C21—H21A	108.4
C7—C8—H8	120.2	C22—C21—H21A	108.4
C8—C9—C1	118.1 (3)	N2—C21—H21B	108.4
C8—C9—C11	119.1 (3)	C22—C21—H21B	108.4
C1—C9—C11	122.9 (3)	H21A—C21—H21B	107.5
O1—C10—H10A	109.5	O3—C22—N3	122.5 (3)
O1—C10—H10B	109.5	O3—C22—C21	121.4 (3)
H10A—C10—H10B	109.5	N3—C22—C21	116.1 (3)
O1—C10—H10C	109.5	N3—C23—C24	112.9 (3)
H10A—C10—H10C	109.5	N3—C23—H23A	109.0
H10B—C10—H10C	109.5	C24—C23—H23A	109.0
O2—C11—C9	110.1 (2)	N3—C23—H23B	109.0
O2—C11—C12	110.0 (2)	C24—C23—H23B	109.0
C9—C11—C12	109.8 (2)	H23A—C23—H23B	107.8
O2—C11—H11	109.0	C23—C24—H24A	109.5
C9—C11—H11	109.0	C23—C24—H24B	109.5
C12—C11—H11	109.0	H24A—C24—H24B	109.5
C13—C12—C11	113.6 (3)	C23—C24—H24C	109.5
C13—C12—N2	107.7 (2)	H24A—C24—H24C	109.5
C11—C12—N2	114.0 (2)	H24B—C24—H24C	109.5
C13—C12—H12	107.0	N3—C25—C26	112.5 (3)
C11—C12—H12	107.0	N3—C25—H25A	109.1
N2—C12—H12	107.0	C26—C25—H25A	109.1
C12—C13—C14	109.9 (2)	N3—C25—H25B	109.1
C12—C13—H13A	109.7	C26—C25—H25B	109.1
C14—C13—H13A	109.7	H25A—C25—H25B	107.8
C12—C13—H13B	109.7	C25—C26—H26A	109.5
C14—C13—H13B	109.7	C25—C26—H26B	109.5
H13A—C13—H13B	108.2	H26A—C26—H26B	109.5
C19—C14—C15	109.1 (3)	C25—C26—H26C	109.5
C19—C14—C13	106.5 (3)	H26A—C26—H26C	109.5
C15—C14—C13	109.7 (3)	H26B—C26—H26C	109.5

C9—C1—C2—C3	−178.8 (3)	C16—N2—C12—C11	−160.6 (2)
C6—C1—C2—C3	−1.0 (5)	C20—N2—C12—C11	84.3 (3)
C10—O1—C3—C2	9.8 (6)	C11—C12—C13—C14	−150.9 (3)
C10—O1—C3—C4	−170.9 (4)	N2—C12—C13—C14	−23.6 (3)
C1—C2—C3—O1	−179.6 (3)	C12—C13—C14—C19	74.2 (3)
C1—C2—C3—C4	1.0 (5)	C12—C13—C14—C15	−43.7 (4)
O1—C3—C4—C5	−179.7 (4)	C19—C14—C15—C17	−176.2 (3)
C2—C3—C4—C5	−0.3 (6)	C13—C14—C15—C17	−59.8 (4)
C3—C4—C5—C6	−0.5 (6)	C19—C14—C15—C16	−48.0 (3)
C4—C5—C6—N1	−179.7 (4)	C13—C14—C15—C16	68.3 (3)
C4—C5—C6—C1	0.5 (5)	C21—N2—C16—C15	−173.8 (2)
C9—C1—C6—N1	−1.6 (5)	C20—N2—C16—C15	71.1 (3)
C2—C1—C6—N1	−179.6 (3)	C12—N2—C16—C15	−47.5 (3)
C9—C1—C6—C5	178.2 (3)	C17—C15—C16—N2	107.2 (3)
C2—C1—C6—C5	0.2 (4)	C14—C15—C16—N2	−19.1 (3)
C5—C6—N1—C7	−178.2 (3)	C15—C14—C19—C20	67.4 (4)
C1—C6—N1—C7	1.6 (5)	C13—C14—C19—C20	−50.9 (4)
C6—N1—C7—C8	0.1 (5)	C14—C19—C20—N2	−14.0 (4)
N1—C7—C8—C9	−1.8 (5)	C21—N2—C20—C19	−168.1 (3)
C7—C8—C9—C1	1.7 (5)	C16—N2—C20—C19	−51.2 (3)
C7—C8—C9—C11	−179.1 (3)	C12—N2—C20—C19	64.9 (3)
C2—C1—C9—C8	177.7 (3)	C14—C15—C17—C18	133.4 (5)
C6—C1—C9—C8	−0.1 (4)	C16—C15—C17—C18	9.1 (6)
C2—C1—C9—C11	−1.5 (5)	C16—N2—C21—C22	66.6 (3)
C6—C1—C9—C11	−179.4 (3)	C20—N2—C21—C22	−179.1 (3)
C8—C9—C11—O2	−9.1 (4)	C12—N2—C21—C22	−55.0 (3)
C1—C9—C11—O2	170.2 (3)	C23—N3—C22—O3	3.5 (5)
C8—C9—C11—C12	112.2 (3)	C25—N3—C22—O3	−174.3 (3)
C1—C9—C11—C12	−68.6 (4)	C23—N3—C22—C21	−174.8 (3)
O2—C11—C12—C13	70.3 (3)	C25—N3—C22—C21	7.4 (5)
C9—C11—C12—C13	−51.0 (3)	N2—C21—C22—O3	3.3 (4)
O2—C11—C12—N2	−53.6 (3)	N2—C21—C22—N3	−178.4 (3)
C9—C11—C12—N2	−175.0 (2)	C22—N3—C23—C24	86.3 (4)
C21—N2—C12—C13	−164.9 (2)	C25—N3—C23—C24	−95.7 (4)
C16—N2—C12—C13	72.3 (3)	C22—N3—C25—C26	96.8 (4)
C20—N2—C12—C13	−42.8 (3)	C23—N3—C25—C26	−81.1 (4)
C21—N2—C12—C11	−37.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1	0.82	2.25	3.038 (2)	161
C19—H19A···Cl1ⁱ	0.97	2.70	3.580 (4)	150
C20—H20B···O2	0.97	2.33	3.001 (4)	126
C21—H21B···Cl1	0.97	2.76	3.650 (3)	152
C21—H21B···O2	0.97	2.58	3.169 (4)	119

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₆N₃O₃⁺·Cl⁻·H₂O
M_r	492.04
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	8.2213 (12), 17.441 (3), 18.161 (3)
V (Å³)	2604.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.938, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	15334, 5361, 3043
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.111, 1.00
No. of reflections	5361
No. of parameters	311
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18
Absolute structure	Flack (1983), 2317 Friedel pairs
Absolute structure parameter	0.14 (9)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl1	0.82	2.25	3.038 (2)	161
C19—H19A···Cl1ⁱ	0.97	2.70	3.580 (4)	150
C20—H20B···O2	0.97	2.33	3.001 (4)	126
C21—H21B···Cl1	0.97	2.76	3.650 (3)	152
C21—H21B···O2	0.97	2.58	3.169 (4)	119

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge financial support from the Youth Foundation of Jiangnan University (grant No. 104000-52210691).

References

Bruker (1998). SMART. Version 5.2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT (Version 5.2) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Oleksyn, B., Lebioda, Ł. & Ciechanowicz-Rutkowska, M. (1979). Acta Cryst. B35, 440–444. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, L. P., Chen, X. D., Lv, J. & Wang, Y. M. (2006). J. Mol. Struct. 789, 169–176. Web of Science CSD CrossRef CAS Google Scholar

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

1-[(Di­ethyl­amino­carbon­yl)meth­yl]-2-[hydr­­oxy(6-meth­oxy­quinolin-4-yl)meth­yl]-5-vinyl-1-azoniabi­cyclo­[2.2.2]octane chloride monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[(Diethylaminocarbonyl)methyl]-2-[hydroxy(6-methoxyquinolin-4-yl)methyl]-5-vinyl-1-azoniabicyclo[2.2.2]octane chloride monohydrate