(9-Anthryl­methyl)­tri­methyl­ammonium chloride monohydrate

Beaudry, C.M.; Pehl, J.; Wovkulich, K.M.

doi:10.1107/S1600536803011280

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(9-Anthrylmethyl)trimethylammonium chloride monohydrate

C. M. Beaudry, J. Pehl and K. M. Wovkulich

The title compound, C₁₈H₂₀N⁺·Cl^-·H₂O, contains a tetraalkylammonium chloride functionality bound to an anthryl moiety. There are two formula units in the asymmetric unit of the crystal structure, with a dihedral angle of 22.55 (1)° between the anthryl planes.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011280/fl6038sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011280/fl6038Isup2.hkl Contains datablock I

CCDC reference: 214862

checkCIF report

Key indicators

Single-crystal X-ray study
T = 148 K
Mean (C-C) = 0.008 Å
R factor = 0.044
wR factor = 0.054
Data-to-parameter ratio = 8.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
          Tmin and Tmax reported:      0.800     0.970
          Tmin' and Tmax expected:      0.946     0.972
          RR' =      0.847
          Please check that your absorption correction is appropriate.

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5884

PLAT_162  Alert C Missing or Zero su (esd) on y-coordinate for .       CL1

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.72
         From the CIF: _reflns_number_total               4282
         Count of symmetry unique reflns         2932
         Completeness (_total/calc)            146.04%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1350
         Fraction of Friedel pairs measured     0.460
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Comment top

The behavior of anthracene and its derivatives plays a large role in many areas of chemistry including nanoscience (Zhang et al., 2003), organometallic chemistry (Carano et al., 2001), asymmetric organic synthesis (Corey et al., 1997), and biochemical probes (Ihmels et al., 2000; Becker & Norden, 2000). The title compound, (I), has been synthesized from the substitution reaction of trimethyl amine and 9-(chloromethyl)anthracene (Takagi et al., 1983) and recrystallized from acetonitrile.

The compound crystallizes with two molecules of (I) in the asymmetric unit. The cationic N atoms have tetrahedral geometry and form ion pairs with the chloride counter-ions. The N···Cl distances (N1···Cl1 = 3.99 Å and N2···Cl2 = 4.03 Å) are consistent with reported values in similar compounds (for a recent example, see Corey et al., 1997). Each chloride ion is hydrogen bonded to two water molecules, one in the asymmetric unit and one symmetry-related water molecule with distances Cl1···O1 = 3.191 (5) Å, Cl1···O1' = 3.178 (6) Å, Cl2···O2 = 3.190 (5) Å and Cl2···O2'' = 3.158 (4) Å.

The closest contact between the two anthryl moieties within the asymmetric unit is C3···C29 of 3.427 (8) Å. The dihedral angle between anthracene planes is 22.55°, indicative of little or no π-stacking. A similar anthracene derivative has been reported (Le Magueres et al., 2000). This previously reported structure exhibits a dihedral angle between layers (23°) that is similar to that observed here between molecules.

Experimental top

The synthesis of (I) has been described in the literature (Takagi, 1983). Suitable crystals were obtained by slow evaporation of a saturated solution of (I) in wet acetonitrile. The water H atoms were located in the difference Fourier map and their postitions were refined. All other H atoms were calculated geometrically and not refined. Assignment of the correct enantiomorph was accomplished by comparison of the intensities of Friedel pairs of reflections. The correct enantiomorph of the space group is shown in Fig. 1.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: TEXSAN; molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top

Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(I) top

Crystal data top

C₁₈H₂₀N⁺·Cl⁻·H₂O	F(000) = 648.00
M_r = 303.83	D_x = 1.249 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.7107 Å
a = 8.1368 (6) Å	Cell parameters from 3212 reflections
b = 10.2645 (8) Å	θ = 2.5–24.3°
c = 19.351 (2) Å	µ = 0.24 mm⁻¹
β = 92.088 (1)°	T = 148 K
V = 1615.1 (2) Å³	Tablet, yellow
Z = 4	0.23 × 0.15 × 0.12 mm

Data collection top

SMART 1K CCD diffractometer	4282 independent reflections
Radiation source: X-ray tube	3143 reflections with F² > 3σ(F²)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 24.7°, θ_min = 2.5°
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	h = −9→8
T_min = 0.80, T_max = 0.97	k = −11→10
7199 measured reflections	l = −22→22

Refinement top

Refinement on F	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.044	Weighting scheme based on measured s.u.'s
wR(F²) = 0.054	(Δ/σ)_max = 0.007
S = 1.54	Δρ_max = 0.70 e Å⁻³
3143 reflections	Δρ_min = −0.26 e Å⁻³
378 parameters

Crystal data top

C₁₈H₂₀N⁺·Cl⁻·H₂O	V = 1615.1 (2) Å³
M_r = 303.83	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.1368 (6) Å	µ = 0.24 mm⁻¹
b = 10.2645 (8) Å	T = 148 K
c = 19.351 (2) Å	0.23 × 0.15 × 0.12 mm
β = 92.088 (1)°

Data collection top

SMART 1K CCD diffractometer	4282 independent reflections
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	3143 reflections with F² > 3σ(F²)
T_min = 0.80, T_max = 0.97	R_int = 0.057
7199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.54	Δρ_max = 0.70 e Å⁻³
3143 reflections	Δρ_min = −0.26 e Å⁻³
378 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	−0.8729 (2)	−0.4608	0.01010 (7)	0.0317 (4)
Cl2	−0.3544 (2)	−0.5452 (2)	−0.48686 (7)	0.0313 (4)
O1	−1.1640 (5)	−0.2587 (5)	0.0326 (3)	0.072 (2)
O2	−0.3419 (4)	−0.8532 (4)	−0.5084 (2)	0.042 (1)
N1	−0.6536 (5)	−0.1345 (5)	−0.0504 (2)	0.015 (1)
N2	−0.1511 (4)	−0.1949 (4)	−0.4454 (2)	0.020 (1)
C1	−0.7789 (5)	−0.1706 (5)	−0.1725 (2)	0.027 (1)
C2	−0.7310 (6)	−0.2876 (5)	−0.2058 (2)	0.014 (1)
C3	−0.7174 (6)	−0.4108 (6)	−0.1715 (3)	0.022 (2)
C4	−0.6697 (7)	−0.5203 (5)	−0.2061 (3)	0.030 (2)
C5	−0.6338 (7)	−0.5128 (6)	−0.2771 (3)	0.036 (2)
C6	−0.6475 (7)	−0.3996 (7)	−0.3117 (3)	0.030 (2)
C7	−0.6967 (6)	−0.2831 (6)	−0.2779 (3)	0.021 (2)
C8	−0.7114 (6)	−0.1665 (6)	−0.3142 (2)	0.018 (2)
C9	−0.7655 (6)	−0.0540 (6)	−0.2826 (2)	0.022 (1)
C10	−0.7884 (6)	0.0645 (6)	−0.3216 (3)	0.022 (2)
C11	−0.8482 (7)	0.1723 (6)	−0.2925 (3)	0.030 (2)
C12	−0.8874 (6)	0.1709 (6)	−0.2223 (3)	0.039 (2)
C13	−0.8671 (6)	0.0627 (5)	−0.1832 (2)	0.022 (2)
C14	−0.8034 (5)	−0.0554 (6)	−0.2111 (2)	0.019 (1)
C15	−0.8060 (5)	−0.1706 (5)	−0.0958 (2)	0.018 (1)
C16	−0.5764 (6)	−0.0094 (5)	−0.0707 (3)	0.032 (2)
C17	−0.7066 (7)	−0.1240 (6)	0.0226 (3)	0.028 (2)
C18	−0.5271 (6)	−0.2408 (5)	−0.0539 (3)	0.018 (2)
C19	−0.2742 (5)	−0.1882 (6)	−0.3243 (2)	0.017 (1)
C20	−0.3007 (6)	−0.0623 (5)	−0.2971 (2)	0.022 (1)
C21	−0.3583 (6)	0.0449 (6)	−0.3389 (2)	0.024 (2)
C22	−0.3825 (7)	0.1656 (6)	−0.3106 (3)	0.028 (2)
C23	−0.3581 (6)	0.1857 (6)	−0.2388 (3)	0.025 (2)
C24	−0.3038 (7)	0.0875 (6)	−0.1968 (3)	0.022 (2)
C25	−0.2765 (6)	−0.0394 (6)	−0.2248 (2)	0.023 (1)
C26	−0.2247 (6)	−0.1398 (6)	−0.1814 (2)	0.030 (2)
C27	−0.2019 (6)	−0.2662 (5)	−0.2057 (2)	0.017 (2)
C28	−0.1522 (6)	−0.3686 (6)	−0.1603 (3)	0.038 (2)
C29	−0.1259 (7)	−0.4893 (6)	−0.1845 (3)	0.032 (2)
C30	−0.1535 (7)	−0.5175 (5)	−0.2552 (3)	0.034 (2)
C31	−0.2037 (6)	−0.4235 (6)	−0.3002 (3)	0.017 (2)
C32	−0.2261 (6)	−0.2920 (5)	−0.2789 (2)	0.009 (1)
C33	−0.3010 (5)	−0.2135 (5)	−0.4006 (2)	0.017 (1)
C34	−0.0254 (6)	−0.2980 (5)	−0.4307 (3)	0.028 (2)
C35	−0.2098 (7)	−0.2058 (6)	−0.5197 (2)	0.047 (2)
C36	−0.0711 (6)	−0.0654 (6)	−0.4348 (2)	0.027 (2)
H1	−0.7416	−0.4167	−0.1239	0.0259
H2	−0.6611	−0.6011	−0.1824	0.0360
H3	−0.5994	−0.5886	−0.3006	0.0427
H4	−0.6242	−0.3970	−0.3595	0.0356
H5	−0.6833	−0.1634	−0.3615	0.0210
H6	−0.7599	0.0664	−0.3688	0.0268
H7	−0.8648	0.2496	−0.3193	0.0357
H8	−0.9288	0.2481	−0.2019	0.0471
H9	−0.8959	0.0652	−0.1361	0.0262
H10	−0.8907	−0.1097	−0.0867	0.0217
H11	−0.8404	−0.2553	−0.0829	0.0217
H12	−0.5388	−0.0163	−0.1165	0.0389
H13	−0.4859	0.0095	−0.0399	0.0389
H14	−0.6550	0.0590	−0.0688	0.0389
H15	−0.7836	−0.0549	0.0260	0.0336
H16	−0.6135	−0.1069	0.0522	0.0336
H17	−0.7562	−0.2035	0.0357	0.0336
H18	−0.5744	−0.3210	−0.0407	0.0214
H19	−0.4364	−0.2207	−0.0233	0.0214
H20	−0.4902	−0.2473	−0.0998	0.0214
H21	−0.3804	0.0322	−0.3868	0.0283
H22	−0.4158	0.2366	−0.3396	0.0337
H23	−0.3801	0.2691	−0.2197	0.0305
H24	−0.2844	0.1032	−0.1487	0.0266
H25	−0.2041	−0.1220	−0.1337	0.0362
H26	−0.1371	−0.3515	−0.1122	0.0461
H27	−0.0883	−0.5556	−0.1537	0.0388
H28	−0.1370	−0.6035	−0.2715	0.0407
H29	−0.2246	−0.4455	−0.3473	0.0200
H30	−0.3373	−0.3008	−0.4059	0.0209
H31	−0.3849	−0.1558	−0.4172	0.0209
H32	−0.0744	−0.3812	−0.4367	0.0338
H33	0.0166	−0.2891	−0.3845	0.0338
H34	0.0620	−0.2887	−0.4616	0.0338
H35	−0.2866	−0.1381	−0.5302	0.0569
H36	−0.2611	−0.2878	−0.5270	0.0569
H37	−0.1188	−0.1979	−0.5488	0.0569
H38	0.0166	−0.0562	−0.4656	0.0322
H39	−0.0290	−0.0585	−0.3885	0.0322
H40	−0.1495	0.0019	−0.4436	0.0322
H41	−0.4565	−0.9074	−0.5019	0.0592
H42	−0.3636	−0.7705	−0.4995	0.0592
H43	−1.0685	−0.2843	0.0273	0.0592
H44	−1.1298	−0.1784	0.0028	0.0592

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0449 (9)	0.045 (1)	0.0363 (8)	−0.0122 (7)	−0.0028 (7)	0.0137 (7)
Cl2	0.0409 (8)	0.0380 (10)	0.0464 (8)	−0.0033 (8)	0.0019 (7)	−0.0083 (8)
O1	0.030 (2)	0.091 (4)	0.105 (4)	−0.003 (2)	0.004 (2)	0.051 (3)
O2	0.032 (2)	0.045 (3)	0.049 (2)	0.005 (2)	0.005 (2)	0.006 (2)
N1	0.025 (2)	0.030 (3)	0.020 (2)	−0.005 (2)	−0.005 (2)	0.001 (2)
N2	0.022 (2)	0.026 (3)	0.024 (2)	0.002 (2)	0.006 (2)	−0.004 (2)
C1	0.018 (3)	0.023 (3)	0.020 (3)	−0.002 (2)	0.003 (2)	−0.003 (2)
C2	0.019 (3)	0.023 (3)	0.028 (3)	0.000 (2)	−0.003 (2)	−0.002 (2)
C3	0.027 (3)	0.023 (3)	0.038 (3)	0.001 (3)	−0.002 (2)	0.001 (3)
C4	0.028 (3)	0.019 (4)	0.055 (4)	0.004 (3)	−0.001 (3)	−0.004 (3)
C5	0.028 (3)	0.027 (4)	0.065 (4)	0.006 (3)	0.008 (3)	−0.017 (3)
C6	0.027 (3)	0.045 (4)	0.040 (4)	0.003 (3)	0.004 (3)	−0.018 (3)
C7	0.020 (3)	0.029 (4)	0.030 (3)	−0.002 (2)	−0.001 (2)	−0.007 (3)
C8	0.025 (3)	0.046 (4)	0.018 (3)	−0.005 (3)	0.000 (2)	0.000 (3)
C9	0.023 (3)	0.024 (3)	0.023 (3)	−0.007 (3)	−0.001 (2)	0.002 (3)
C10	0.033 (3)	0.042 (4)	0.029 (3)	−0.012 (3)	−0.008 (2)	0.010 (3)
C11	0.041 (4)	0.027 (4)	0.039 (4)	−0.005 (3)	−0.009 (3)	0.013 (3)
C12	0.028 (3)	0.026 (4)	0.042 (4)	0.004 (3)	−0.008 (3)	0.000 (3)
C13	0.028 (3)	0.027 (4)	0.030 (3)	0.004 (3)	0.000 (2)	−0.002 (3)
C14	0.015 (2)	0.023 (3)	0.027 (3)	−0.002 (2)	−0.004 (2)	0.002 (2)
C15	0.016 (2)	0.021 (3)	0.034 (3)	0.001 (2)	−0.001 (2)	0.000 (2)
C16	0.032 (3)	0.036 (4)	0.029 (3)	−0.005 (3)	−0.007 (2)	−0.002 (2)
C17	0.036 (3)	0.047 (4)	0.025 (3)	−0.004 (3)	0.001 (2)	−0.005 (3)
C18	0.031 (3)	0.030 (4)	0.037 (3)	0.007 (3)	−0.008 (2)	0.003 (2)
C19	0.016 (3)	0.024 (3)	0.025 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C20	0.018 (3)	0.025 (3)	0.028 (3)	0.000 (2)	0.004 (2)	0.002 (3)
C21	0.030 (3)	0.029 (4)	0.024 (3)	0.007 (3)	0.003 (2)	−0.003 (3)
C22	0.040 (4)	0.022 (4)	0.039 (3)	0.006 (3)	0.009 (3)	0.005 (3)
C23	0.027 (3)	0.025 (4)	0.045 (4)	0.002 (3)	0.013 (3)	−0.005 (3)
C24	0.036 (3)	0.031 (4)	0.028 (3)	−0.009 (3)	0.005 (2)	−0.009 (3)
C25	0.019 (2)	0.024 (3)	0.028 (3)	−0.004 (3)	0.004 (2)	0.001 (3)
C26	0.025 (3)	0.034 (4)	0.023 (3)	−0.007 (3)	0.001 (2)	−0.005 (3)
C27	0.017 (3)	0.030 (4)	0.027 (3)	0.001 (2)	−0.001 (2)	0.003 (3)
C28	0.026 (3)	0.032 (4)	0.037 (3)	−0.005 (3)	0.002 (3)	0.007 (3)
C29	0.031 (3)	0.041 (4)	0.042 (3)	0.008 (3)	0.007 (3)	0.014 (3)
C30	0.032 (3)	0.018 (4)	0.045 (3)	0.003 (3)	0.007 (3)	0.004 (3)
C31	0.025 (3)	0.030 (4)	0.033 (3)	−0.004 (3)	0.004 (2)	−0.002 (3)
C32	0.019 (3)	0.025 (3)	0.026 (3)	−0.001 (2)	0.004 (2)	−0.002 (2)
C33	0.022 (3)	0.022 (3)	0.025 (3)	0.000 (2)	0.005 (2)	−0.003 (2)
C34	0.033 (3)	0.025 (3)	0.039 (3)	0.006 (3)	0.006 (2)	−0.006 (3)
C35	0.053 (4)	0.049 (4)	0.020 (3)	0.002 (3)	0.003 (3)	−0.006 (3)
C36	0.024 (3)	0.031 (4)	0.036 (3)	−0.002 (3)	0.004 (2)	−0.002 (3)

Geometric parameters (Å, º) top

N1—C15	1.539 (6)	O1—H44	1.0494 (1)
N1—C16	1.488 (6)	O2—H41	1.0967 (1)
N1—C17	1.495 (6)	O2—H42	0.8857 (1)
N1—C18	1.503 (6)	C3—H1	0.9500 (1)
N2—C33	1.535 (6)	C4—H2	0.9500 (1)
N2—C34	1.492 (7)	C5—H3	0.9500 (1)
N2—C35	1.503 (6)	C6—H4	0.9500 (1)
N2—C36	1.490 (7)	C8—H5	0.9500 (1)
C1—C2	1.423 (7)	C10—H6	0.9500 (1)
C1—C14	1.408 (7)	C11—H7	0.9500 (1)
C1—C15	1.510 (6)	C12—H8	0.9500 (1)
C2—C3	1.430 (7)	C13—H9	0.9500 (1)
C2—C7	1.434 (7)	C15—H10	0.9500 (1)
C3—C4	1.372 (7)	C15—H11	0.9500 (1)
C4—C5	1.418 (8)	C16—H12	0.9500 (1)
C5—C6	1.343 (8)	C16—H13	0.9500 (1)
C6—C7	1.428 (8)	C16—H14	0.9500 (1)
C7—C8	1.391 (7)	C17—H15	0.9500 (1)
C8—C9	1.387 (7)	C17—H16	0.9500 (1)
C9—C10	1.440 (8)	C17—H17	0.9500 (1)
C9—C14	1.427 (6)	C18—H18	0.9500 (1)
C10—C11	1.341 (8)	C18—H19	0.9500 (1)
C11—C12	1.407 (7)	C18—H20	0.9500 (1)
C12—C13	1.350 (7)	C21—H21	0.9500 (1)
C13—C14	1.432 (7)	C22—H22	0.9500 (1)
C19—C20	1.416 (7)	C23—H23	0.9500 (1)
C19—C32	1.427 (7)	C24—H24	0.9500 (1)
C19—C33	1.505 (7)	C26—H25	0.9500 (1)
C20—C21	1.434 (7)	C28—H26	0.9500 (1)
C20—C25	1.424 (7)	C29—H27	0.9500 (1)
C21—C22	1.371 (8)	C30—H28	0.9500 (1)
C22—C23	1.412 (7)	C31—H29	0.9500 (1)
C23—C24	1.359 (8)	C33—H30	0.9500 (1)
C24—C25	1.431 (7)	C33—H31	0.9500 (1)
C25—C26	1.385 (7)	C34—H32	0.9500 (1)
C26—C27	1.395 (7)	C34—H33	0.9500 (1)
C27—C28	1.419 (7)	C34—H34	0.9500 (1)
C27—C32	1.447 (7)	C35—H35	0.9500 (1)
C28—C29	1.344 (8)	C35—H36	0.9500 (1)
C29—C30	1.409 (8)	C35—H37	0.9500 (1)
C30—C31	1.352 (7)	C36—H38	0.9500 (1)
C31—C32	1.425 (7)	C36—H39	0.9500 (1)
O1—H43	0.8304 (1)	C36—H40	0.9500 (1)

C15—N1—C16	113.4 (3)	C11—C12—C13	121.5 (5)
C15—N1—C17	107.6 (3)	C12—C13—C14	121.6 (5)
C15—N1—C18	109.8 (4)	C1—C14—C9	119.3 (5)
C16—N1—C17	109.0 (4)	C1—C14—C13	123.9 (4)
C16—N1—C18	108.5 (4)	C9—C14—C13	116.8 (5)
C17—N1—C18	108.4 (4)	N1—C15—C1	114.7 (3)
C33—N2—C34	110.9 (4)	C20—C19—C32	119.6 (4)
C33—N2—C35	107.5 (4)	C20—C19—C33	120.3 (4)
C33—N2—C36	112.7 (4)	C32—C19—C33	120.1 (5)
C34—N2—C35	108.7 (4)	C19—C20—C21	122.8 (4)
C34—N2—C36	108.2 (4)	C19—C20—C25	119.9 (5)
C35—N2—C36	108.7 (4)	C21—C20—C25	117.2 (5)
C2—C1—C14	120.3 (4)	C20—C21—C22	121.1 (5)
C2—C1—C15	119.8 (4)	C21—C22—C23	120.5 (5)
C14—C1—C15	119.9 (4)	C22—C23—C24	120.7 (5)
C1—C2—C3	123.7 (4)	C23—C24—C25	120.0 (5)
C1—C2—C7	118.6 (5)	C20—C25—C24	120.3 (5)
C3—C2—C7	117.7 (5)	C20—C25—C26	120.1 (5)
C2—C3—C4	121.1 (5)	C24—C25—C26	119.6 (5)
C3—C4—C5	120.0 (5)	C25—C26—C27	121.9 (5)
C4—C5—C6	120.9 (5)	C26—C27—C28	121.3 (5)
C5—C6—C7	121.1 (5)	C26—C27—C32	119.0 (5)
C2—C7—C6	119.1 (5)	C28—C27—C32	119.7 (5)
C2—C7—C8	120.2 (5)	C27—C28—C29	120.8 (5)
C6—C7—C8	120.7 (5)	C28—C29—C30	120.4 (5)
C7—C8—C9	121.1 (5)	C29—C30—C31	120.8 (5)
C8—C9—C10	120.6 (5)	C30—C31—C32	122.0 (5)
C8—C9—C14	120.2 (5)	C19—C32—C27	119.4 (5)
C10—C9—C14	119.2 (5)	C19—C32—C31	124.4 (4)
C9—C10—C11	121.3 (5)	C27—C32—C31	116.2 (5)
C10—C11—C12	119.6 (5)	N2—C33—C19	116.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H43···Cl1	0.83	2.44	3.190 (5)	150
O1—H44···Cl1ⁱ	1.05	2.25	3.185 (5)	148
O2—H41···Cl2ⁱⁱ	1.10	2.10	3.159 (4)	163
O2—H42···Cl2	0.89	2.33	3.191 (5)	165

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N⁺·Cl⁻·H₂O
M_r	303.83
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	148
a, b, c (Å)	8.1368 (6), 10.2645 (8), 19.351 (2)
β (°)	92.088 (1)
V (Å³)	1615.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.23 × 0.15 × 0.12

Data collection
Diffractometer	SMART 1K CCD diffractometer
Absorption correction	Empirical (using intensity measurements) (Blessing, 1995)
T_min, T_max	0.80, 0.97
No. of measured, independent and observed [F² > 3σ(F²)] reflections	7199, 4282, 3143
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.054, 1.54
No. of reflections	3143
No. of parameters	378
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.26

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1992), TEXSAN.

Selected geometric parameters (Å, º) top

N1—C15	1.539 (6)	N2—C33	1.535 (6)
N1—C16	1.488 (6)	N2—C34	1.492 (7)
N1—C17	1.495 (6)	N2—C35	1.503 (6)
N1—C18	1.503 (6)	N2—C36	1.490 (7)

C15—N1—C16	113.4 (3)	C33—N2—C35	107.5 (4)
C15—N1—C17	107.6 (3)	C33—N2—C36	112.7 (4)
C15—N1—C18	109.8 (4)	C34—N2—C35	108.7 (4)
C16—N1—C17	109.0 (4)	C34—N2—C36	108.2 (4)
C16—N1—C18	108.5 (4)	C35—N2—C36	108.7 (4)
C17—N1—C18	108.4 (4)	N1—C15—C1	114.7 (3)
C33—N2—C34	110.9 (4)	N2—C33—C19	116.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H43···Cl1	0.83	2.44	3.190 (5)	150
O1—H44···Cl1ⁱ	1.05	2.25	3.185 (5)	148
O2—H41···Cl2ⁱⁱ	1.10	2.10	3.159 (4)	163
O2—H42···Cl2	0.89	2.33	3.191 (5)	165

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

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