Cinchonidinium chloride monohydrate

Ni, S.-F.; Ma, L.L.; Zhao, G.F.; Sun, W.J.; Jin, Z.M.

doi:10.1107/S160053680706343X

organic compounds

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Volume 64| Part 1| January 2008| Page o193

https://doi.org/10.1107/S160053680706343X

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Cinchonidinium chloride monohydrate

Shi-Feng Ni,^a Lin Lin Ma,^b Gui Fang Zhao,^a Wen Ji Sun ^a and Zhi Min Jin ^b ^*

^aKey Laboratory of Resource Biology and Biotechnology in Western China (Northwest University), Ministry of Education, College of Life Sciences, Northwest University, Xi'an 710069, People's Republic of China, and ^bCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: apharm@sina.com

(Received 23 November 2007; accepted 26 November 2007; online 6 December 2007)

In the title salt, C₁₉H₂₃N₂O⁺·Cl⁻·H₂O, the ions and the water molecule are held together by O—H⋯Cl, N—H⋯Cl, O—H⋯O, O—H⋯N and C—H⋯Cl hydrogen bonds, forming a three-dimensional framework. The vinyl group is disordered over two orientations with refined occupancies of 0.564 (16) and 0.436 (16). The cell parameters of the title compound have been reported previously [Griffiths (1952 ). Acta Cryst. 5, 290–291].

Related literature

For the Cambridge Structural Database (Version 5.26), see: Allen (2002 ). For related literature, see: Griffiths (1952); Zhang, Lü et al. (2006 ); Zhang, Tu et al. (2006 ).

Experimental

Crystal data

C₁₉H₂₃N₂O⁺·Cl⁻·H₂O
M_r = 348.86
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.4924 (8) Å
b = 12.9049 (10) Å
c = 13.3936 (10) Å
V = 1813.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 273 (2) K
0.37 × 0.34 × 0.12 mm

Data collection

Siemens P4 diffractometer
Absorption correction: multi-scan (SHELXTL; Bruker, 1998 ) T_min = 0.722, T_max = 0.895 (expected range = 0.785–0.973)
9572 measured reflections
3214 independent reflections
3090 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections every 97 reflections intensity decay: 5.0%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.179
S = 1.18
3214 reflections
252 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1369 Friedel pairs
Flack parameter: 0.04 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82 (2)	1.84 (2)	2.653 (5)	172 (3)
O2—H2OB⋯N1ⁱⁱ	0.82 (2)	2.07 (2)	2.867 (6)	165 (3)
O2—H2OA⋯Cl1	0.82 (2)	2.31 (2)	3.135 (5)	174 (6)
N2—H2⋯Cl1	0.96 (4)	2.08 (4)	3.034 (6)	175 (3)
C5—H5⋯Cl1	0.93	2.77	3.692 (5)	172
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053680706343X/ci2530sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706343X/ci2530Isup2.hkl

checkCIF report

Comment top

The cell parameters (a = 12.8, b = 13.3, c = 10.6 Å) of the title compound have been reported previously (Griffiths, 1952; CSD refcode ZZZTZW, CSD, Version 5.26; Allen, 2002), but structural details are not available. Crystal structures of some compounds containing cinchonidine have also been reported, e.g. cinchonidinium bis(4-methylbenzenesulfonate) monohydrate (Zhang, Lü et al., 2006), cinchonidinium bis(perchlorate) (Zhang, Tu et al., 2006).

The geometry of the cinchonidinium unit is consistent with that observed in other cinchonidinium compounds (Zhang, Lv et al., 2006; Zhang, Tu et al., 2006), except for the disorder in the vinyl group. The C—C bond lengths in quinoline ring system range from 1.358 (6) to 1.429 (6) Å, comparable with the range of 1.344 (5)–1.422 (4) Å observed by Zhang, Lv et al. (2006).

As shown in Fig. 1, the chloride anion and cinchonidinium cation are linked by N—H···Cl and weak C—H···Cl hydrogen bonds, and the chloride ion and water molecule are connected by a O—H···Cl hydrogen bond (Table 1). The ionic pairs and water molecule are linked by O—H···N and O—H···O hydrogen bonds to form a three-dimensional framework (Fig. 2).

Related literature top

For the Cambridge Structural Database, see: Allen (2002). For related literature, see: Griffiths (1952); Zhang, Lü et al. (2006); Zhang, Tu et al. (2006).

Experimental top

Cinchonidine (0.01 mol, 2.94 g) and 10% hydrochloric acid (3.65 g) were mixed together with enough water, and heated to a temperature where a clear solution was resulted. Colourless single crystals of the title compound were obtained by slow evaporation of the solution at room temperature for 7 d.

Structure description top

For the Cambridge Structural Database, see: Allen (2002). For related literature, see: Griffiths (1952); Zhang, Lü et al. (2006); Zhang, Tu et al. (2006).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Cinchonidinium chloride monohydrate top

Crystal data top

C₁₉H₂₃N₂O⁺·Cl⁻·H₂O	F(000) = 744
M_r = 348.86	D_x = 1.278 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 31 reflections
a = 10.4924 (8) Å	θ = 3.3–18.6°
b = 12.9049 (10) Å	µ = 0.22 mm⁻¹
c = 13.3936 (10) Å	T = 273 K
V = 1813.5 (2) Å³	Plate, colourless
Z = 4	0.37 × 0.34 × 0.12 mm

Data collection top

Siemens P4 diffractometer	3090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −12→11
Absorption correction: multi-scan (SHELXTL; Bruker, 1998)	k = −9→15
T_min = 0.722, T_max = 0.895	l = −15→15
9572 measured reflections	3 standard reflections every 97 reflections
3214 independent reflections	intensity decay: 5.0%

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)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.179	w = 1/[σ²(F_o²) + (0.0981P)² + 0.5633P] where P = (F_o² + 2F_c²)/3
S = 1.18	(Δ/σ)_max = 0.001
3214 reflections	Δρ_max = 0.31 e Å⁻³
252 parameters	Δρ_min = −0.21 e Å⁻³
12 restraints	Absolute structure: Flack (1983), with 1369 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (13)

Crystal data top

C₁₉H₂₃N₂O⁺·Cl⁻·H₂O	V = 1813.5 (2) Å³
M_r = 348.86	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.4924 (8) Å	µ = 0.22 mm⁻¹
b = 12.9049 (10) Å	T = 273 K
c = 13.3936 (10) Å	0.37 × 0.34 × 0.12 mm

Data collection top

Siemens P4 diffractometer	3090 reflections with I > 2σ(I)
Absorption correction: multi-scan (SHELXTL; Bruker, 1998)	R_int = 0.031
T_min = 0.722, T_max = 0.895	3 standard reflections every 97 reflections
9572 measured reflections	intensity decay: 5.0%
3214 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.179	Δρ_max = 0.31 e Å⁻³
S = 1.18	Δρ_min = −0.21 e Å⁻³
3214 reflections	Absolute structure: Flack (1983), with 1369 Friedel pairs
252 parameters	Absolute structure parameter: 0.04 (13)
12 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	Occ. (<1)
Cl1	0.94217 (9)	0.75097 (9)	0.35617 (7)	0.0500 (3)
O1	0.7326 (3)	0.9410 (2)	0.1041 (2)	0.0511 (8)
O2	1.0407 (3)	0.5216 (3)	0.3556 (4)	0.0858 (13)
N1	0.6545 (4)	0.6294 (3)	−0.1087 (2)	0.0510 (9)
N2	0.6840 (3)	0.8504 (3)	0.3211 (2)	0.0454 (8)
C1	0.6176 (4)	0.7257 (4)	−0.1063 (3)	0.0533 (12)
H1A	0.5696	0.7497	−0.1599	0.064*
C2	0.6443 (4)	0.7957 (4)	−0.0297 (3)	0.0478 (10)
H2A	0.6143	0.8634	−0.0333	0.057*
C3	0.7148 (3)	0.7642 (3)	0.0508 (3)	0.0381 (9)
C4	0.7589 (3)	0.6594 (3)	0.0517 (3)	0.0346 (8)
C5	0.8343 (4)	0.6152 (3)	0.1287 (3)	0.0422 (9)
H5	0.8546	0.6549	0.1844	0.051*
C6	0.8775 (4)	0.5162 (3)	0.1227 (3)	0.0482 (10)
H6	0.9271	0.4890	0.1739	0.058*
C7	0.8475 (4)	0.4552 (4)	0.0401 (3)	0.0527 (11)
H7	0.8781	0.3877	0.0361	0.063*
C8	0.7738 (4)	0.4939 (4)	−0.0349 (3)	0.0489 (10)
H8	0.7533	0.4522	−0.0892	0.059*
C9	0.7288 (4)	0.5953 (3)	−0.0310 (3)	0.0397 (9)
C10	0.7394 (3)	0.8374 (3)	0.1368 (3)	0.0363 (8)
H10	0.8246	0.8241	0.1638	0.044*
C11	0.6392 (4)	0.8168 (3)	0.2187 (3)	0.0410 (9)
H11	0.6269	0.7416	0.2216	0.049*
C12	0.5101 (4)	0.8640 (5)	0.2001 (4)	0.0668 (15)
H12A	0.4511	0.8109	0.1780	0.080*
H12B	0.5163	0.9162	0.1482	0.080*
C13	0.4614 (5)	0.9137 (5)	0.2972 (4)	0.0701 (15)
H13	0.3743	0.9388	0.2869	0.084*
C14	0.4621 (5)	0.8368 (4)	0.3821 (3)	0.0615 (13)
H14	0.4334	0.8725	0.4426	0.074*
C15	0.5996 (5)	0.8022 (4)	0.3980 (3)	0.0620 (13)
H15A	0.6277	0.8227	0.4642	0.074*
H15B	0.6048	0.7273	0.3934	0.074*
C16	0.5460 (6)	1.0037 (4)	0.3240 (5)	0.0831 (18)
H16A	0.5175	1.0346	0.3861	0.100*
H16B	0.5420	1.0560	0.2721	0.100*
C17	0.6826 (5)	0.9649 (4)	0.3353 (4)	0.0613 (13)
H17A	0.7369	0.9978	0.2860	0.074*
H17B	0.7147	0.9822	0.4011	0.074*
C18	0.3877 (9)	0.7331 (8)	0.3733 (7)	0.050 (3)	0.564 (16)
H18	0.4218	0.6754	0.4051	0.061*	0.564 (16)
C19	0.2832 (9)	0.7210 (9)	0.3257 (8)	0.067 (3)	0.564 (16)
H19A	0.2460	0.7768	0.2929	0.081*	0.564 (16)
H19B	0.2443	0.6562	0.3239	0.081*	0.564 (16)
C18'	0.3393 (10)	0.7759 (9)	0.3550 (12)	0.080 (6)	0.436 (16)
H18'	0.2713	0.8063	0.3215	0.096*	0.436 (16)
C19'	0.338 (2)	0.6812 (10)	0.3823 (11)	0.079 (5)	0.436 (16)
H19C	0.4083	0.6535	0.4158	0.094*	0.436 (16)
H19D	0.2680	0.6398	0.3687	0.094*	0.436 (16)
H2	0.765 (4)	0.820 (3)	0.336 (3)	0.035 (10)*
H1	0.803 (3)	0.967 (4)	0.111 (4)	0.062 (16)*
H2OA	1.020 (4)	0.5832 (15)	0.358 (5)	0.081 (18)*
H2OB	0.982 (3)	0.480 (2)	0.354 (4)	0.061 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0518 (5)	0.0549 (6)	0.0432 (5)	0.0083 (5)	−0.0100 (4)	−0.0045 (5)
O1	0.0510 (18)	0.0404 (16)	0.0618 (18)	−0.0074 (14)	−0.0066 (15)	0.0044 (14)
O2	0.0468 (19)	0.051 (2)	0.160 (4)	0.0026 (17)	0.002 (3)	0.012 (3)
N1	0.053 (2)	0.059 (2)	0.0405 (18)	−0.0011 (18)	−0.0096 (16)	−0.0068 (17)
N2	0.0440 (19)	0.053 (2)	0.0387 (17)	0.0083 (17)	−0.0003 (14)	−0.0012 (16)
C1	0.056 (2)	0.066 (3)	0.038 (2)	0.000 (2)	−0.0127 (19)	0.006 (2)
C2	0.051 (2)	0.044 (2)	0.048 (2)	0.002 (2)	−0.005 (2)	0.0043 (18)
C3	0.0346 (18)	0.047 (2)	0.0329 (18)	−0.0061 (18)	0.0032 (14)	0.0078 (17)
C4	0.0298 (17)	0.045 (2)	0.0294 (18)	−0.0013 (16)	0.0031 (14)	0.0000 (16)
C5	0.047 (2)	0.045 (2)	0.0344 (19)	−0.0088 (18)	−0.0041 (17)	−0.0029 (17)
C6	0.051 (2)	0.045 (2)	0.048 (2)	0.0081 (19)	−0.008 (2)	0.0003 (19)
C7	0.057 (3)	0.042 (2)	0.059 (3)	0.011 (2)	0.004 (2)	−0.001 (2)
C8	0.056 (2)	0.050 (2)	0.041 (2)	−0.005 (2)	−0.0007 (19)	−0.0162 (19)
C9	0.0357 (19)	0.049 (2)	0.0347 (18)	−0.0030 (18)	0.0058 (16)	−0.0030 (17)
C10	0.0369 (18)	0.0347 (18)	0.0374 (18)	−0.0003 (16)	−0.0076 (16)	0.0005 (16)
C11	0.042 (2)	0.043 (2)	0.038 (2)	−0.0058 (18)	−0.0023 (16)	0.0026 (17)
C12	0.040 (2)	0.113 (4)	0.047 (3)	0.007 (3)	0.0029 (19)	0.009 (3)
C13	0.045 (3)	0.092 (4)	0.073 (3)	0.019 (3)	0.008 (2)	0.005 (3)
C14	0.061 (3)	0.076 (3)	0.048 (3)	−0.011 (3)	0.021 (2)	−0.015 (2)
C15	0.090 (4)	0.060 (3)	0.036 (2)	0.002 (3)	0.011 (2)	0.003 (2)
C16	0.086 (4)	0.053 (3)	0.110 (5)	0.019 (3)	0.031 (4)	0.006 (3)
C17	0.073 (3)	0.056 (3)	0.055 (3)	−0.011 (2)	0.011 (2)	−0.013 (2)
C18	0.068 (6)	0.026 (6)	0.058 (5)	−0.010 (5)	0.005 (4)	0.008 (4)
C19	0.078 (7)	0.051 (7)	0.072 (7)	−0.015 (5)	0.003 (5)	−0.019 (5)
C18'	0.108 (15)	0.040 (8)	0.092 (11)	0.033 (9)	0.034 (11)	−0.006 (9)
C19'	0.115 (13)	0.046 (8)	0.075 (10)	−0.012 (9)	−0.007 (9)	−0.010 (7)

Geometric parameters (Å, º) top

O1—C10	1.409 (5)	C11—C12	1.505 (6)
O1—H1	0.82 (2)	C11—H11	0.98
O2—H2OA	0.823 (19)	C12—C13	1.538 (7)
O2—H2OB	0.816 (18)	C12—H12A	0.97
N1—C1	1.302 (6)	C12—H12B	0.97
N1—C9	1.372 (5)	C13—C16	1.506 (9)
N2—C17	1.490 (6)	C13—C14	1.508 (7)
N2—C15	1.495 (6)	C13—H13	0.98
N2—C11	1.512 (5)	C14—C15	1.524 (7)
N2—H2	0.96 (4)	C14—C18'	1.552 (12)
C1—C2	1.395 (6)	C14—C18	1.554 (9)
C1—H1A	0.93	C14—H14	0.98
C2—C3	1.370 (6)	C15—H15A	0.97
C2—H2A	0.93	C15—H15B	0.97
C3—C4	1.429 (6)	C16—C17	1.525 (8)
C3—C10	1.512 (5)	C16—H16A	0.97
C4—C9	1.419 (5)	C16—H16B	0.97
C4—C5	1.419 (5)	C17—H17A	0.97
C5—C6	1.358 (6)	C17—H17B	0.97
C5—H5	0.93	C18—C19	1.278 (11)
C6—C7	1.394 (6)	C18—H18	0.93
C6—H6	0.93	C19—H19A	0.93
C7—C8	1.363 (6)	C19—H19B	0.93
C7—H7	0.93	C18'—C19'	1.277 (12)
C8—C9	1.391 (6)	C18'—H18'	0.93
C8—H8	0.93	C19'—H19C	0.93
C10—C11	1.543 (5)	C19'—H19D	0.93
C10—H10	0.98

C10—O1—H1	108 (4)	C13—C12—H12A	109.9
H2OA—O2—H2OB	116 (3)	C11—C12—H12B	109.9
C1—N1—C9	117.1 (3)	C13—C12—H12B	109.9
C17—N2—C15	108.6 (4)	H12A—C12—H12B	108.3
C17—N2—C11	113.4 (3)	C16—C13—C14	109.0 (5)
C15—N2—C11	108.8 (3)	C16—C13—C12	109.1 (5)
C17—N2—H2	113 (2)	C14—C13—C12	111.2 (4)
C15—N2—H2	102 (2)	C16—C13—H13	109.2
C11—N2—H2	110 (2)	C14—C13—H13	109.2
N1—C1—C2	125.2 (4)	C12—C13—H13	109.2
N1—C1—H1A	117.4	C13—C14—C15	107.6 (4)
C2—C1—H1A	117.4	C13—C14—C18'	98.8 (7)
C3—C2—C1	119.6 (4)	C15—C14—C18'	132.1 (6)
C3—C2—H2A	120.2	C13—C14—C18	120.4 (5)
C1—C2—H2A	120.2	C15—C14—C18	103.5 (5)
C2—C3—C4	117.6 (4)	C13—C14—H14	108.2
C2—C3—C10	120.4 (4)	C15—C14—H14	108.2
C4—C3—C10	122.0 (3)	C18'—C14—H14	100.1
C9—C4—C5	117.2 (4)	C18—C14—H14	108.2
C9—C4—C3	118.2 (3)	N2—C15—C14	110.0 (4)
C5—C4—C3	124.5 (3)	N2—C15—H15A	109.7
C6—C5—C4	121.4 (4)	C14—C15—H15A	109.7
C6—C5—H5	119.3	N2—C15—H15B	109.7
C4—C5—H5	119.3	C14—C15—H15B	109.7
C5—C6—C7	120.2 (4)	H15A—C15—H15B	108.2
C5—C6—H6	119.9	C13—C16—C17	108.9 (4)
C7—C6—H6	119.9	C13—C16—H16A	109.9
C8—C7—C6	120.4 (4)	C17—C16—H16A	109.9
C8—C7—H7	119.8	C13—C16—H16B	109.9
C6—C7—H7	119.8	C17—C16—H16B	109.9
C7—C8—C9	120.6 (4)	H16A—C16—H16B	108.3
C7—C8—H8	119.7	N2—C17—C16	108.8 (4)
C9—C8—H8	119.7	N2—C17—H17A	109.9
N1—C9—C8	117.8 (4)	C16—C17—H17A	109.9
N1—C9—C4	122.1 (4)	N2—C17—H17B	109.9
C8—C9—C4	120.1 (4)	C16—C17—H17B	109.9
O1—C10—C3	110.4 (3)	H17A—C17—H17B	108.3
O1—C10—C11	110.5 (3)	C19—C18—C14	125.1 (11)
C3—C10—C11	108.5 (3)	C19—C18—H18	117.4
O1—C10—H10	109.1	C14—C18—H18	117.4
C3—C10—H10	109.1	C18—C19—H19A	120.0
C11—C10—H10	109.1	C18—C19—H19B	120.0
C12—C11—N2	108.3 (4)	H19A—C19—H19B	120.0
C12—C11—C10	115.2 (3)	C19'—C18'—C14	115.1 (13)
N2—C11—C10	112.6 (3)	C19'—C18'—H18'	122.4
C12—C11—H11	106.8	C14—C18'—H18'	122.4
N2—C11—H11	106.8	C18'—C19'—H19C	120.0
C10—C11—H11	106.8	C18'—C19'—H19D	120.0
C11—C12—C13	109.1 (4)	H19C—C19'—H19D	120.0
C11—C12—H12A	109.9

C9—N1—C1—C2	−2.0 (7)	C3—C10—C11—C12	−79.1 (5)
N1—C1—C2—C3	0.1 (7)	O1—C10—C11—N2	−82.8 (4)
C1—C2—C3—C4	0.4 (6)	C3—C10—C11—N2	156.1 (3)
C1—C2—C3—C10	−177.1 (4)	N2—C11—C12—C13	−9.2 (5)
C2—C3—C4—C9	0.9 (5)	C10—C11—C12—C13	−136.2 (4)
C10—C3—C4—C9	178.5 (3)	C11—C12—C13—C16	65.9 (6)
C2—C3—C4—C5	179.0 (4)	C11—C12—C13—C14	−54.3 (6)
C10—C3—C4—C5	−3.4 (5)	C16—C13—C14—C15	−59.0 (5)
C9—C4—C5—C6	0.9 (6)	C12—C13—C14—C15	61.3 (5)
C3—C4—C5—C6	−177.2 (4)	C16—C13—C14—C18'	161.5 (6)
C4—C5—C6—C7	−0.3 (6)	C12—C13—C14—C18'	−78.3 (6)
C5—C6—C7—C8	−0.6 (7)	C16—C13—C14—C18	−177.2 (6)
C6—C7—C8—C9	1.0 (7)	C12—C13—C14—C18	−56.9 (7)
C1—N1—C9—C8	−177.1 (4)	C17—N2—C15—C14	64.0 (5)
C1—N1—C9—C4	3.5 (6)	C11—N2—C15—C14	−59.8 (5)
C7—C8—C9—N1	−179.7 (4)	C13—C14—C15—N2	−3.6 (5)
C7—C8—C9—C4	−0.3 (6)	C18'—C14—C15—N2	116.6 (9)
C5—C4—C9—N1	178.8 (4)	C18—C14—C15—N2	125.0 (5)
C3—C4—C9—N1	−3.0 (5)	C14—C13—C16—C17	63.4 (6)
C5—C4—C9—C8	−0.6 (5)	C12—C13—C16—C17	−58.2 (6)
C3—C4—C9—C8	177.6 (4)	C15—N2—C17—C16	−59.6 (5)
C2—C3—C10—O1	−25.4 (5)	C11—N2—C17—C16	61.4 (5)
C4—C3—C10—O1	157.1 (3)	C13—C16—C17—N2	−2.9 (6)
C2—C3—C10—C11	95.8 (4)	C13—C14—C18—C19	−33.2 (12)
C4—C3—C10—C11	−81.6 (4)	C15—C14—C18—C19	−153.4 (10)
C17—N2—C11—C12	−53.9 (5)	C18'—C14—C18—C19	13.9 (13)
C15—N2—C11—C12	67.0 (5)	C13—C14—C18'—C19'	150.7 (12)
C17—N2—C11—C10	74.6 (4)	C15—C14—C18'—C19'	27.2 (17)
C15—N2—C11—C10	−164.5 (3)	C18—C14—C18'—C19'	10.5 (12)
O1—C10—C11—C12	42.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82 (2)	1.84 (2)	2.653 (5)	172 (3)
O2—H2OB···N1ⁱⁱ	0.82 (2)	2.07 (2)	2.867 (6)	165 (3)
O2—H2OA···Cl1	0.82 (2)	2.31 (2)	3.135 (5)	174 (6)
N2—H2···Cl1	0.96 (4)	2.08 (4)	3.034 (6)	175 (3)
C5—H5···Cl1	0.93	2.77	3.692 (5)	172

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+3/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃N₂O⁺·Cl⁻·H₂O
M_r	348.86
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	273
a, b, c (Å)	10.4924 (8), 12.9049 (10), 13.3936 (10)
V (Å³)	1813.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.34 × 0.12

Data collection
Diffractometer	Siemens P4
Absorption correction	Multi-scan (SHELXTL; Bruker, 1998)
T_min, T_max	0.722, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	9572, 3214, 3090
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.179, 1.18
No. of reflections	3214
No. of parameters	252
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.21
Absolute structure	Flack (1983), with 1369 Friedel pairs
Absolute structure parameter	0.04 (13)

Computer programs: XSCANS (Siemens, 1994), SHELXTL (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82 (2)	1.84 (2)	2.653 (5)	172 (3)
O2—H2OB···N1ⁱⁱ	0.82 (2)	2.07 (2)	2.867 (6)	165 (3)
O2—H2OA···Cl1	0.82 (2)	2.31 (2)	3.135 (5)	174 (6)
N2—H2···Cl1	0.96 (4)	2.08 (4)	3.034 (6)	175 (3)
C5—H5···Cl1	0.93	2.77	3.692 (5)	172

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+3/2, −y+1, z+1/2.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (1998). SHELXTL. 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
Griffiths, P. J. F. (1952). Acta Cryst. 5, 290–291. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Siemens (1994). XSCANS. Version 2.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Zhang, H.-M., Lü, Y.-P., Tu, B., Jin, Z.-M. & Wu, Z.-Y. (2006). Acta Cryst. E62, o3398–o3400. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, H.-M., Tu, B., Jin, Z.-M., Wu, Z.-Y. & Hu, M.-L. (2006). Acta Cryst. E62, o2614–o2616. Web of Science CSD CrossRef IUCr Journals Google Scholar

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