rac-18-Meth­oxy­coronaridine hydro­chloride

Kuehne, M.E.; Waterman, R.

doi:10.1107/S1600536812009981

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1041

doi:10.1107/S1600536812009981

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rac-18-Methoxycoronaridine hydrochloride

Martin E. Kuehne ^a and Rory Waterman ^a ^*

^aDepartment of Chemistry, University of Vermont, 82 University Place, Burlington, VT 05405, USA
^*Correspondence e-mail: rory.waterman@uvm.edu

(Received 16 February 2012; accepted 6 March 2012; online 10 March 2012)

In the crystal structure of the racemic title compound, C₂₂H₂₉N₂O₃⁺·Cl⁻, both NH groups form N—H⋯Cl hydrogen bonds with the chloride counter-ion, forming translational chains along the a axis.

Related literature

The title compound is a prospective anti-addictive and antileishmaniasis agent. For the synsthesis of the free base along with some bio-activity studies, see: Bandarage et al. (1995 ). For a study of related systems, see: Kuehne et al. (2003 ).

Experimental

Crystal data

C₂₂H₂₉N₂O₃⁺·Cl⁻
M_r = 404.92
Monoclinic, P 2₁ /n
a = 9.3692 (14) Å
b = 20.161 (3) Å
c = 11.6281 (18) Å
β = 110.221 (2)°
V = 2061.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 125 K
0.21 × 0.17 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.958, T_max = 0.983
22802 measured reflections
4374 independent reflections
2620 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.118
S = 1.01
4374 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯Cl	1.01 (3)	2.09 (3)	3.054 (2)	160 (3)
N1—H1⋯Clⁱ	0.93 (3)	2.25 (3)	3.157 (2)	165 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536812009981/ld2049sup1.cif

Supporting information file. DOI: 10.1107/S1600536812009981/ld2049Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009981/ld2049Isup3.hkl

checkCIF report

Comment top

18-Methoxycoronaridine hydrochloride is a compound under investigation for anti-addictive and anti-leishmaniasis activity (Bandarage, et al., 1995) that has prompted a further study on additional, related systems (Kuehne, et al., 2003). Its structure is presented herein to aid these studies. The hydrochloride salt is readily obtained from pure 18-methoxycoronaridine by reaction with anhydrous hydrochloric acid. Though this salt readily crystalizes from a variety of solvents, it was found that ethanol/THF was the optimal system for affording X-ray quality samples. Desipte the conditions, no evidence for decarbomethoxylation was observed.

Related literature top

The title compound is a prospective anti-addictive and antileishmaniasis agent. For the synsthesis of the free base along with some bio-activity studies, see: Bandarage et al. (1995). For a study of related systems, see: Kuehne et al. (2003).

Experimental top

18-Methoxycoronaridine was prepared according to the literature procedure (Bandarage et al., 1995) and treated in dichloromethane solution with excess of anhydrous HCl. The solvent was removed under reduced pressure, and the the residue was washed with benzene that gave the pure 18-methoxycoronaridine hydrochloride (sub: 195–197 C). X-ray quality crystals were grown from a methanol/THF solvent mixutre.

Structure description top

The title compound is a prospective anti-addictive and antileishmaniasis agent. For the synsthesis of the free base along with some bio-activity studies, see: Bandarage et al. (1995). For a study of related systems, see: Kuehne et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Structure of 18-methoxycoronaridine hydrochloride with elipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity except for H1 and H4.

(1RS,13RS,17SR)-1-(methoxycarbonyl)-17-(2-methoxyethyl)- 3,13-diazapentacyclo[13.3.1.0^2,10.0^4,9.0^13,18]nonadeca- 2(10),4,6,8-tetraen-13-ium chloride top

Crystal data top

C₂₂H₂₉N₂O₃⁺·Cl⁻	F(000) = 864
M_r = 404.92	D_x = 1.305 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4279 reflections
a = 9.3692 (14) Å	θ = 2.5–26.9°
b = 20.161 (3) Å	µ = 0.21 mm⁻¹
c = 11.6281 (18) Å	T = 125 K
β = 110.221 (2)°	Plate, colourless
V = 2061.1 (5) Å³	0.21 × 0.17 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4374 independent reflections
Radiation source: fine-focus sealed tube	2620 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
φ and ω scans	θ_max = 26.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.958, T_max = 0.983	k = −25→25
22802 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0445P)² + 0.8261P] where P = (F_o² + 2F_c²)/3
4374 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₂H₂₉N₂O₃⁺·Cl⁻	V = 2061.1 (5) Å³
M_r = 404.92	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3692 (14) Å	µ = 0.21 mm⁻¹
b = 20.161 (3) Å	T = 125 K
c = 11.6281 (18) Å	0.21 × 0.17 × 0.08 mm
β = 110.221 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4374 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2620 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.983	R_int = 0.100
22802 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.31 e Å⁻³
4374 reflections	Δρ_min = −0.32 e Å⁻³
261 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. Suitable crystals were mounted in a nylon loop with Paratone-N cryoprotectant oil and data collected on a Bruker APEX 2 CCD platform diffractometer. The structure was solved using direct methods and standard difference map techniques, and was refined by full-matrix least-squares procedures on F2 with SHELXTL Version 6.14 (Sheldrick, 2008).

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
C2	−0.6298 (3)	−0.03049 (13)	0.2437 (2)	0.0159 (6)
C3	−0.3327 (3)	0.04266 (13)	0.4114 (2)	0.0204 (6)
H11A	−0.2318	0.0509	0.4745	0.024*
H11B	−0.3874	0.0099	0.4441	0.024*
C5	−0.2795 (3)	−0.05676 (13)	0.2987 (2)	0.0195 (6)
H10A	−0.1936	−0.0632	0.2687	0.023*
H10B	−0.2456	−0.0720	0.3849	0.023*
C6	−0.4102 (3)	−0.10020 (13)	0.2237 (2)	0.0194 (6)
H12C	−0.4299	−0.0918	0.1357	0.023*
H12D	−0.3796	−0.1472	0.2402	0.023*
C7	−0.5551 (3)	−0.08957 (13)	0.2490 (2)	0.0178 (6)
C8	−0.6388 (3)	−0.13907 (13)	0.2870 (2)	0.0177 (6)
C9	−0.6179 (3)	−0.20695 (13)	0.3122 (2)	0.0224 (6)
H12A	−0.5347	−0.2298	0.3015	0.027*
C10	−0.7204 (3)	−0.24016 (14)	0.3529 (3)	0.0268 (7)
H12B	−0.7063	−0.2861	0.3714	0.032*
C11	−0.8452 (3)	−0.20713 (14)	0.3674 (2)	0.0249 (7)
H11E	−0.9144	−0.2313	0.3949	0.030*
C12	−0.8691 (3)	−0.14076 (13)	0.3427 (2)	0.0204 (6)
H18A	−0.9534	−0.1186	0.3528	0.024*
C13	−0.7655 (3)	−0.10689 (13)	0.3021 (2)	0.0179 (6)
C14	−0.4234 (3)	0.10731 (13)	0.3792 (2)	0.0180 (6)
H10C	−0.4145	0.1323	0.4557	0.022*
C15	−0.3613 (3)	0.14888 (13)	0.2976 (2)	0.0198 (6)
H19A	−0.2491	0.1518	0.3343	0.024*
H19B	−0.4034	0.1944	0.2898	0.024*
C16	−0.5960 (3)	0.03842 (12)	0.2080 (2)	0.0152 (6)
C17	−0.5909 (3)	0.09052 (13)	0.3084 (2)	0.0178 (6)
H11C	−0.6468	0.1310	0.2699	0.021*
H11D	−0.6393	0.0722	0.3649	0.021*
C18	−0.2695 (3)	0.19660 (14)	0.0775 (3)	0.0237 (6)
H11H	−0.2384	0.2229	0.1541	0.028*
H11I	−0.1882	0.2000	0.0415	0.028*
C19	−0.2917 (3)	0.12482 (13)	0.1052 (2)	0.0212 (6)
H11F	−0.1927	0.1062	0.1575	0.025*
H11G	−0.3258	0.0995	0.0275	0.025*
C20	−0.4076 (3)	0.11564 (12)	0.1697 (2)	0.0170 (6)
H18B	−0.5047	0.1368	0.1170	0.020*
C21	−0.4422 (3)	0.04253 (13)	0.1856 (2)	0.0172 (6)
H17A	−0.4478	0.0167	0.1108	0.021*
C22	−0.7202 (3)	0.05207 (13)	0.0837 (2)	0.0165 (6)
C98	−0.9699 (3)	0.08902 (16)	−0.0188 (3)	0.0345 (8)
H12E	−1.0560	0.1086	−0.0015	0.052*
H12F	−1.0004	0.0462	−0.0600	0.052*
H12G	−0.9381	0.1189	−0.0719	0.052*
C99	−0.3917 (4)	0.28863 (14)	−0.0384 (3)	0.0377 (8)
H11J	−0.4889	0.3044	−0.0963	0.057*
H11K	−0.3136	0.2912	−0.0766	0.057*
H11L	−0.3617	0.3164	0.0354	0.057*
N1	−0.7580 (2)	−0.04105 (11)	0.27505 (19)	0.0167 (5)
N4	−0.3142 (2)	0.01673 (11)	0.29607 (19)	0.0174 (5)
H4	−0.214 (4)	0.0360 (15)	0.299 (3)	0.048 (10)*
O1	−0.4075 (2)	0.22182 (9)	−0.00591 (17)	0.0262 (5)
O2	−0.7097 (2)	0.03754 (9)	−0.01348 (16)	0.0256 (5)
O3	−0.84383 (19)	0.07907 (9)	0.09564 (16)	0.0246 (5)
Cl	0.02001 (7)	0.05216 (3)	0.35272 (6)	0.02537 (18)
H1	−0.824 (3)	−0.0090 (14)	0.285 (2)	0.027 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0138 (13)	0.0207 (15)	0.0116 (12)	−0.0009 (11)	0.0022 (10)	0.0002 (11)
C3	0.0189 (14)	0.0267 (16)	0.0138 (13)	0.0020 (12)	0.0034 (11)	−0.0005 (11)
C5	0.0169 (14)	0.0194 (15)	0.0208 (14)	0.0057 (12)	0.0049 (11)	0.0016 (12)
C6	0.0181 (14)	0.0185 (15)	0.0218 (14)	0.0031 (11)	0.0070 (11)	−0.0004 (12)
C7	0.0169 (14)	0.0206 (15)	0.0143 (13)	0.0019 (11)	0.0032 (11)	−0.0017 (11)
C8	0.0166 (14)	0.0199 (15)	0.0132 (13)	−0.0003 (11)	0.0011 (11)	−0.0018 (11)
C9	0.0188 (15)	0.0226 (16)	0.0223 (15)	0.0011 (12)	0.0027 (12)	−0.0009 (12)
C10	0.0295 (17)	0.0168 (15)	0.0300 (17)	−0.0018 (12)	0.0052 (13)	0.0031 (13)
C11	0.0215 (15)	0.0263 (17)	0.0246 (16)	−0.0081 (12)	0.0051 (13)	0.0018 (12)
C12	0.0133 (14)	0.0265 (16)	0.0192 (14)	−0.0028 (11)	0.0030 (11)	0.0002 (12)
C13	0.0152 (14)	0.0218 (15)	0.0135 (13)	−0.0018 (11)	0.0009 (11)	−0.0001 (11)
C14	0.0174 (13)	0.0205 (15)	0.0147 (13)	0.0023 (11)	0.0039 (11)	−0.0026 (11)
C15	0.0162 (14)	0.0202 (15)	0.0209 (14)	−0.0022 (11)	0.0038 (11)	−0.0034 (12)
C16	0.0108 (13)	0.0189 (15)	0.0140 (13)	0.0011 (10)	0.0018 (10)	0.0008 (11)
C17	0.0170 (14)	0.0197 (15)	0.0170 (14)	0.0015 (11)	0.0062 (11)	−0.0001 (11)
C18	0.0190 (15)	0.0273 (16)	0.0254 (15)	−0.0024 (12)	0.0085 (12)	0.0014 (13)
C19	0.0179 (14)	0.0253 (16)	0.0204 (15)	0.0014 (12)	0.0065 (12)	0.0016 (12)
C20	0.0141 (13)	0.0195 (15)	0.0159 (13)	0.0011 (11)	0.0035 (11)	0.0024 (11)
C21	0.0134 (13)	0.0230 (16)	0.0133 (13)	0.0013 (11)	0.0021 (10)	−0.0004 (11)
C22	0.0151 (13)	0.0151 (14)	0.0192 (14)	−0.0010 (11)	0.0059 (11)	0.0007 (11)
C98	0.0188 (16)	0.052 (2)	0.0237 (16)	0.0125 (14)	−0.0035 (13)	−0.0020 (15)
C99	0.051 (2)	0.0228 (18)	0.044 (2)	0.0058 (15)	0.0223 (17)	0.0096 (15)
N1	0.0133 (11)	0.0181 (13)	0.0187 (12)	0.0011 (9)	0.0052 (9)	−0.0012 (9)
N4	0.0141 (12)	0.0219 (13)	0.0135 (11)	0.0006 (9)	0.0013 (9)	0.0005 (9)
O1	0.0247 (11)	0.0212 (11)	0.0329 (12)	0.0015 (8)	0.0103 (9)	0.0061 (9)
O2	0.0212 (10)	0.0398 (13)	0.0148 (10)	0.0043 (9)	0.0049 (8)	−0.0033 (9)
O3	0.0162 (10)	0.0372 (12)	0.0175 (10)	0.0087 (8)	0.0019 (8)	−0.0009 (8)
Cl	0.0161 (3)	0.0283 (4)	0.0299 (4)	0.0018 (3)	0.0056 (3)	−0.0024 (3)

Geometric parameters (Å, º) top

C2—C7	1.372 (4)	C15—H19B	0.9900
C2—N1	1.387 (3)	C16—C22	1.535 (3)
C2—C16	1.514 (3)	C16—C21	1.552 (3)
C3—N4	1.504 (3)	C16—C17	1.559 (3)
C3—C14	1.530 (3)	C17—H11C	0.9900
C3—H11A	0.9900	C17—H11D	0.9900
C3—H11B	0.9900	C18—O1	1.416 (3)
C5—C6	1.513 (3)	C18—C19	1.512 (4)
C5—N4	1.515 (3)	C18—H11H	0.9900
C5—H10A	0.9900	C18—H11I	0.9900
C5—H10B	0.9900	C19—C20	1.530 (3)
C6—C7	1.500 (3)	C19—H11F	0.9900
C6—H12C	0.9900	C19—H11G	0.9900
C6—H12D	0.9900	C20—C21	1.534 (4)
C7—C8	1.430 (4)	C20—H18B	1.0000
C8—C9	1.399 (4)	C21—N4	1.515 (3)
C8—C13	1.416 (4)	C21—H17A	1.0000
C9—C10	1.381 (4)	C22—O2	1.204 (3)
C9—H12A	0.9500	C22—O3	1.330 (3)
C10—C11	1.406 (4)	C98—O3	1.456 (3)
C10—H12B	0.9500	C98—H12E	0.9800
C11—C12	1.371 (4)	C98—H12F	0.9800
C11—H11E	0.9500	C98—H12G	0.9800
C12—C13	1.396 (4)	C99—O1	1.420 (3)
C12—H18A	0.9500	C99—H11J	0.9800
C13—N1	1.372 (3)	C99—H11K	0.9800
C14—C15	1.524 (4)	C99—H11L	0.9800
C14—C17	1.537 (3)	N1—H1	0.93 (3)
C14—H10C	1.0000	N4—Cl	3.054 (2)
C15—C20	1.550 (3)	N4—H4	1.01 (3)
C15—H19A	0.9900

C7—C2—N1	109.2 (2)	C14—C17—C16	108.1 (2)
C7—C2—C16	131.0 (2)	C14—C17—H11C	110.1
N1—C2—C16	119.7 (2)	C16—C17—H11C	110.1
N4—C3—C14	107.7 (2)	C14—C17—H11D	110.1
N4—C3—H11A	110.2	C16—C17—H11D	110.1
C14—C3—H11A	110.2	H11C—C17—H11D	108.4
N4—C3—H11B	110.2	O1—C18—C19	109.2 (2)
C14—C3—H11B	110.2	O1—C18—H11H	109.8
H11A—C3—H11B	108.5	C19—C18—H11H	109.8
C6—C5—N4	115.4 (2)	O1—C18—H11I	109.8
C6—C5—H10A	108.4	C19—C18—H11I	109.8
N4—C5—H10A	108.4	H11H—C18—H11I	108.3
C6—C5—H10B	108.4	C18—C19—C20	113.2 (2)
N4—C5—H10B	108.4	C18—C19—H11F	108.9
H10A—C5—H10B	107.5	C20—C19—H11F	108.9
C7—C6—C5	114.3 (2)	C18—C19—H11G	108.9
C7—C6—H12C	108.7	C20—C19—H11G	108.9
C5—C6—H12C	108.7	H11F—C19—H11G	107.8
C7—C6—H12D	108.7	C19—C20—C21	113.0 (2)
C5—C6—H12D	108.7	C19—C20—C15	114.1 (2)
H12C—C6—H12D	107.6	C21—C20—C15	107.5 (2)
C2—C7—C8	107.1 (2)	C19—C20—H18B	107.3
C2—C7—C6	126.7 (2)	C21—C20—H18B	107.3
C8—C7—C6	126.2 (2)	C15—C20—H18B	107.3
C9—C8—C13	119.0 (2)	N4—C21—C20	107.1 (2)
C9—C8—C7	134.0 (2)	N4—C21—C16	110.39 (19)
C13—C8—C7	106.9 (2)	C20—C21—C16	108.6 (2)
C10—C9—C8	118.8 (3)	N4—C21—H17A	110.2
C10—C9—H12A	120.6	C20—C21—H17A	110.2
C8—C9—H12A	120.6	C16—C21—H17A	110.2
C9—C10—C11	121.1 (3)	O2—C22—O3	123.7 (2)
C9—C10—H12B	119.4	O2—C22—C16	124.0 (2)
C11—C10—H12B	119.4	O3—C22—C16	112.3 (2)
C12—C11—C10	121.3 (3)	O3—C98—H12E	109.5
C12—C11—H11E	119.3	O3—C98—H12F	109.5
C10—C11—H11E	119.3	H12E—C98—H12F	109.5
C11—C12—C13	117.8 (3)	O3—C98—H12G	109.5
C11—C12—H18A	121.1	H12E—C98—H12G	109.5
C13—C12—H18A	121.1	H12F—C98—H12G	109.5
N1—C13—C12	130.4 (2)	O1—C99—H11J	109.5
N1—C13—C8	107.7 (2)	O1—C99—H11K	109.5
C12—C13—C8	121.9 (2)	H11J—C99—H11K	109.5
C15—C14—C3	108.7 (2)	O1—C99—H11L	109.5
C15—C14—C17	109.0 (2)	H11J—C99—H11L	109.5
C3—C14—C17	108.8 (2)	H11K—C99—H11L	109.5
C15—C14—H10C	110.1	C13—N1—C2	109.0 (2)
C3—C14—H10C	110.1	C13—N1—H1	123.8 (17)
C17—C14—H10C	110.1	C2—N1—H1	126.9 (17)
C14—C15—C20	108.6 (2)	C3—N4—C21	109.59 (19)
C14—C15—H19A	110.0	C3—N4—C5	114.3 (2)
C20—C15—H19A	110.0	C21—N4—C5	117.03 (19)
C14—C15—H19B	110.0	C3—N4—Cl	98.72 (14)
C20—C15—H19B	110.0	C21—N4—Cl	123.72 (15)
H19A—C15—H19B	108.3	C5—N4—Cl	91.58 (13)
C2—C16—C22	105.1 (2)	C3—N4—H4	103.3 (18)
C2—C16—C21	112.9 (2)	C21—N4—H4	110.6 (18)
C22—C16—C21	106.13 (19)	C5—N4—H4	100.7 (18)
C2—C16—C17	111.6 (2)	Cl—N4—H4	13.3 (18)
C22—C16—C17	113.6 (2)	C18—O1—C99	111.6 (2)
C21—C16—C17	107.45 (19)	C22—O3—C98	114.9 (2)

N4—C5—C6—C7	−51.3 (3)	C18—C19—C20—C15	−62.8 (3)
N1—C2—C7—C8	−0.9 (3)	C14—C15—C20—C19	−147.6 (2)
C16—C2—C7—C8	−179.2 (2)	C14—C15—C20—C21	−21.4 (3)
N1—C2—C7—C6	−179.1 (2)	C19—C20—C21—N4	80.5 (2)
C16—C2—C7—C6	2.7 (4)	C15—C20—C21—N4	−46.3 (3)
C5—C6—C7—C2	54.5 (4)	C19—C20—C21—C16	−160.3 (2)
C5—C6—C7—C8	−123.3 (3)	C15—C20—C21—C16	72.9 (2)
C2—C7—C8—C9	−177.7 (3)	C2—C16—C21—N4	−54.3 (3)
C6—C7—C8—C9	0.4 (5)	C22—C16—C21—N4	−168.9 (2)
C2—C7—C8—C13	0.7 (3)	C17—C16—C21—N4	69.2 (2)
C6—C7—C8—C13	178.9 (2)	C2—C16—C21—C20	−171.4 (2)
C13—C8—C9—C10	−1.0 (4)	C22—C16—C21—C20	74.0 (2)
C7—C8—C9—C10	177.3 (3)	C17—C16—C21—C20	−47.9 (2)
C8—C9—C10—C11	0.9 (4)	C2—C16—C22—O2	−88.7 (3)
C9—C10—C11—C12	−0.5 (4)	C21—C16—C22—O2	31.2 (3)
C10—C11—C12—C13	0.2 (4)	C17—C16—C22—O2	149.1 (3)
C11—C12—C13—N1	−177.4 (2)	C2—C16—C22—O3	88.4 (2)
C11—C12—C13—C8	−0.3 (4)	C21—C16—C22—O3	−151.7 (2)
C9—C8—C13—N1	178.4 (2)	C17—C16—C22—O3	−33.8 (3)
C7—C8—C13—N1	−0.3 (3)	C12—C13—N1—C2	177.2 (3)
C9—C8—C13—C12	0.8 (4)	C8—C13—N1—C2	−0.2 (3)
C7—C8—C13—C12	−178.0 (2)	C7—C2—N1—C13	0.7 (3)
N4—C3—C14—C15	−44.1 (3)	C16—C2—N1—C13	179.2 (2)
N4—C3—C14—C17	74.5 (2)	C14—C3—N4—C21	−25.3 (3)
C3—C14—C15—C20	71.2 (3)	C14—C3—N4—C5	−158.9 (2)
C17—C14—C15—C20	−47.2 (3)	C14—C3—N4—Cl	105.34 (18)
C7—C2—C16—C22	108.9 (3)	C20—C21—N4—C3	75.1 (2)
N1—C2—C16—C22	−69.2 (3)	C16—C21—N4—C3	−42.9 (3)
C7—C2—C16—C21	−6.4 (4)	C20—C21—N4—C5	−152.6 (2)
N1—C2—C16—C21	175.5 (2)	C16—C21—N4—C5	89.4 (2)
C7—C2—C16—C17	−127.5 (3)	C20—C21—N4—Cl	−40.4 (2)
N1—C2—C16—C17	54.4 (3)	C16—C21—N4—Cl	−158.41 (15)
C15—C14—C17—C16	72.0 (3)	C6—C5—N4—C3	105.4 (2)
C3—C14—C17—C16	−46.4 (3)	C6—C5—N4—C21	−24.7 (3)
C2—C16—C17—C14	103.9 (2)	C6—C5—N4—Cl	−154.30 (19)
C22—C16—C17—C14	−137.5 (2)	C19—C18—O1—C99	−178.0 (2)
C21—C16—C17—C14	−20.4 (3)	O2—C22—O3—C98	1.2 (4)
O1—C18—C19—C20	−63.6 (3)	C16—C22—O3—C98	−175.9 (2)
C18—C19—C20—C21	174.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl	1.01 (3)	2.09 (3)	3.054 (2)	160 (3)
N1—H1···Clⁱ	0.93 (3)	2.25 (3)	3.157 (2)	165 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₉N₂O₃⁺·Cl⁻
M_r	404.92
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	125
a, b, c (Å)	9.3692 (14), 20.161 (3), 11.6281 (18)
β (°)	110.221 (2)
V (Å³)	2061.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.21 × 0.17 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.958, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	22802, 4374, 2620
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.118, 1.01
No. of reflections	4374
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
N4—H4···Cl	1.01 (3)	2.09 (3)	3.054 (2)	160 (3)
N1—H1···Clⁱ	0.93 (3)	2.25 (3)	3.157 (2)	165 (2)

Symmetry code: (i) x−1, y, z.

Acknowledgements

X-ray facilities were provided by the NSF (CHE-1039436 to RW).

References

Bandarage, U., Kuehne, M. E. & Glick, S. (1995). Tetrahedron, 55, 9405–9424. Web of Science CrossRef Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kuehne, M. E., He, L., Jokiel, P. A., Pace, C. J., Fleck, M. W., Maisonneuve, I. M., Glick, S. D. & Bidlack, J. M. (2003). J. Med. Chem. 46, 2716–2730. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar