(+)-Escholinine perchlorate

Nečas, M.; Dostál, J.; Slavík, J.

doi:10.1107/S160053680201512X

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(+)-Escholinine perchlorate

M. Necas, J. Dostál and J. Slavík

(+)-Escholinine perchlorate, C₂₁H₂₆NO₄⁺·ClO₄^-, is a quaternary benzyltetrahydroisoquinoline alkaloid isolated from Eschscholtzia californica. The partially saturated nitrogen heterocycle has an almost regular half-chair conformation, with the N atom lying 0.666 (3) Å out of the plane of the other atoms. The two methoxy groups lie in the plane of their parent benzene ring. The dihedral angle between the two aromatic rings is 31.44 (7)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201512X/cf6195sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680201512X/cf6195Isup2.hkl Contains datablock I

CCDC reference: 197481

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.028
wR factor = 0.067
Data-to-parameter ratio = 11.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.00
         From the CIF: _reflns_number_total               3144
         Count of symmetry unique reflns         1906
         Completeness (_total/calc)            164.95%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1238
         Fraction of Friedel pairs measured     0.650
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

(+)-Escholinine, an N-methyl derivative of (+)-romneine, is a quaternary benzyltetrahydroisoquinoline alkaloid isolated (as the perchlorate of its protonated form) from Eschscholtzia californica Cham. (Papaveraceae) (Slavík & Dolejš, 1973). It is a minor component of the highly polar fraction of alkaloids from this source. Recently, it has been isolated from Romneya coulteri Harv. (Valpuesta et al., 1999). The corresponding tertiary base (+)-romneine also occurs in the same plant species (Stermitz et al., 1966).

(+)-Escholinine perchlorate, (I), possesses a tetrahydroisoquinoline skeleton with a substituted benzyl group attached to C1 (Fig. 1). All bond lengths and angles are within normal ranges. The bond lengths involving tetravalent nitrogen (N2—C1, N2—C3, N2—C16 and N2—C17) are 1.524 (2), 1.509 (3), 1.488 (3) and 1.496 (3) Å, respectively. These are somewhat longer than the corresponding N—C distances in the tertiary tetrahydroisoquinoline alkaloids egenine and armepavine (Dokurno et al., 1993; Marek et al., 1997). The mean of the bond angles around N2 is 109.47°, appropriate for sp³ hybridization. The two methoxy groups at C12 and C13 lie in the plane of their parent benzene ring. The partially saturated nitrogen heterocycle has an almost regular half-chair conformation, with atom N2 lying 0.666 (3) Å out of the least-squares plane C1/C8a/C4a/C4/C3. The dihedral angle between the aromatic rings of the isoquinoline moiety and the benzyl group is 31.44 (7)°.

The molecule of (I) contains one chiral centre, atom C1. From previous steric correlations, it is known that dextrorotatory benzyltetrahydroisoquinoline alkaloids have the S configuration (Šantavý, 1979; Bentley, 1998). In accordance with previous investigations, and with the refinement of the Flack (1983) parameter, the molecule of escholinine in Fig. 1 is depicted as the S enantiomer.

The perchlorate anion is a regular tetrahedron. The mean Cl—O bond length is 1.418 Å. There are no hydrogen bonds and the ions are held together by Coulombic and van der Waals interactions. The isoquinoline rings are stacked in columns parallel to the crystallographic a axis.

Experimental top

(+)-Escholinine was isolated as a perchlorate salt from the roots of Eschscholtzia californica Cham. (Slavík & Dolejš, 1973) and recrystallized from methanol; m.p. 482–483 K, [α]_D²⁵ = +74° (0.3 M in methanol).

Computing details top

Data collection: Xcalibur (Oxford Diffraction Ltd, 2001); cell refinement: Xcalibur; data reduction: Xcalibur; program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. A perspective view of (+)-escholinine perchlorate with the atom numbering. Ellipsoids are drawn at the 50% probability level.

(I) top

Crystal data top

C₂₁H₂₆NO₄⁺·ClO₄⁻	F(000) = 480
M_r = 455.88	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.450 (1) Å	Cell parameters from 500 reflections
b = 17.010 (3) Å	θ = 4.5–27.8°
c = 9.038 (2) Å	µ = 0.23 mm⁻¹
β = 114.32 (3)°	T = 120 K
V = 1043.7 (3) Å³	Prism, colourless
Z = 2	0.40 × 0.40 × 0.20 mm

Data collection top

Kuma KM-4 CCD diffractometer	3001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 25.0°, θ_min = 3.4°
Detector resolution: 0.06 mm pixels mm^-1	h = −8→8
ω scans	k = −20→19
6727 measured reflections	l = −10→9
3144 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.028	w = 1/[σ²(F_o²) + (0.0353P)² + 0.1452P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.067	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.20 e Å⁻³
3144 reflections	Δρ_min = −0.20 e Å⁻³
281 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0106 (15)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1276 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.04 (5)

Crystal data top

C₂₁H₂₆NO₄⁺·ClO₄⁻	V = 1043.7 (3) Å³
M_r = 455.88	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.450 (1) Å	µ = 0.23 mm⁻¹
b = 17.010 (3) Å	T = 120 K
c = 9.038 (2) Å	0.40 × 0.40 × 0.20 mm
β = 114.32 (3)°

Data collection top

Kuma KM-4 CCD diffractometer	3001 reflections with I > 2σ(I)
6727 measured reflections	R_int = 0.035
3144 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.20 e Å⁻³
S = 1.04	Δρ_min = −0.20 e Å⁻³
3144 reflections	Absolute structure: Flack (1983), 1276 Friedel pairs
281 parameters	Absolute structure parameter: −0.04 (5)
1 restraint

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
Cl29	0.04206 (8)	0.06289 (3)	0.08370 (6)	0.02160 (14)
O28	−0.0756 (3)	0.08890 (10)	0.1642 (2)	0.0433 (5)
O27	0.0058 (3)	0.11044 (11)	−0.05612 (19)	0.0371 (4)
O26	0.2430 (2)	0.07085 (15)	0.19146 (19)	0.0560 (6)
O25	−0.0030 (4)	−0.01597 (11)	0.0364 (2)	0.0673 (7)
C1	0.4345 (3)	0.03234 (12)	0.5776 (2)	0.0152 (4)
H1A	0.3487	0.0226	0.4605	0.018*
O22	0.4412 (2)	−0.24707 (9)	0.90425 (18)	0.0277 (4)
O21	0.4109 (2)	−0.25527 (8)	0.64040 (18)	0.0250 (4)
O24	0.9781 (2)	−0.20592 (9)	0.39460 (16)	0.0217 (3)
C5	0.4450 (3)	−0.10299 (13)	0.9166 (2)	0.0209 (5)
H5A	0.4541	−0.1003	1.0244	0.025*
C7	0.4145 (3)	−0.17829 (11)	0.6841 (2)	0.0176 (5)
C19	0.9865 (3)	−0.20774 (14)	0.8413 (2)	0.0248 (5)
H19A	1.0528	−0.2557	0.8975	0.037*
H19B	0.8494	−0.2082	0.8285	0.037*
H19C	1.0541	−0.1617	0.9052	0.037*
C9	0.6428 (3)	0.04954 (12)	0.5914 (2)	0.0176 (5)
H9A	0.6384	0.0966	0.5256	0.021*
H9B	0.7289	0.0618	0.7060	0.021*
C14	0.8057 (3)	−0.08073 (12)	0.3299 (2)	0.0197 (5)
H14A	0.8015	−0.0805	0.2235	0.024*
O23	0.9913 (2)	−0.20434 (9)	0.68597 (16)	0.0199 (3)
N2	0.3486 (3)	0.10224 (10)	0.63232 (19)	0.0172 (4)
C12	0.9047 (3)	−0.14084 (12)	0.5923 (2)	0.0149 (4)
C4A	0.4422 (3)	−0.03480 (13)	0.8294 (2)	0.0169 (5)
C8A	0.4248 (3)	−0.03982 (12)	0.6714 (2)	0.0145 (4)
C6	0.4344 (3)	−0.17285 (13)	0.8421 (2)	0.0187 (5)
C10	0.7314 (3)	−0.01735 (12)	0.5362 (2)	0.0160 (4)
C11	0.8279 (3)	−0.07786 (12)	0.6423 (2)	0.0173 (5)
H11A	0.8410	−0.0757	0.7513	0.021*
C18	0.3916 (4)	−0.29875 (13)	0.7679 (3)	0.0275 (6)
H18A	0.4813	−0.3446	0.7974	0.033*
H18B	0.2548	−0.3180	0.7328	0.033*
C16	0.3633 (4)	0.17594 (12)	0.5492 (3)	0.0240 (5)
H16A	0.3069	0.2196	0.5867	0.036*
H16B	0.2905	0.1697	0.4316	0.036*
H16C	0.5019	0.1870	0.5746	0.036*
C15	0.7207 (3)	−0.01961 (12)	0.3804 (2)	0.0189 (5)
H15A	0.6542	0.0212	0.3064	0.023*
C20	0.9804 (4)	−0.20572 (15)	0.2381 (3)	0.0298 (6)
H20A	1.0419	−0.2542	0.2231	0.045*
H20B	1.0558	−0.1603	0.2284	0.045*
H20C	0.8450	−0.2025	0.1550	0.045*
C8	0.4067 (3)	−0.11286 (13)	0.5944 (2)	0.0172 (4)
H8A	0.3898	−0.1166	0.4845	0.021*
C4	0.4411 (3)	0.04292 (12)	0.9072 (2)	0.0233 (5)
H4A	0.5522	0.0440	1.0159	0.028*
H4B	0.3177	0.0472	0.9231	0.028*
C17	0.1346 (3)	0.08731 (13)	0.5874 (3)	0.0228 (5)
H17A	0.0779	0.1319	0.6219	0.034*
H17B	0.1196	0.0394	0.6414	0.034*
H17C	0.0662	0.0809	0.4695	0.034*
C13	0.8959 (3)	−0.14161 (12)	0.4341 (2)	0.0171 (4)
C3	0.4571 (3)	0.11353 (13)	0.8127 (2)	0.0200 (5)
H3A	0.4031	0.1601	0.8461	0.024*
H3B	0.5978	0.1239	0.8392	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl29	0.0223 (3)	0.0266 (3)	0.0174 (2)	−0.0004 (2)	0.0097 (2)	−0.0025 (2)
O28	0.0476 (12)	0.0484 (12)	0.0505 (11)	0.0100 (9)	0.0371 (10)	0.0013 (9)
O27	0.0391 (11)	0.0447 (11)	0.0251 (9)	0.0025 (9)	0.0108 (8)	0.0109 (8)
O26	0.0223 (9)	0.1190 (18)	0.0229 (8)	−0.0034 (12)	0.0054 (7)	0.0106 (11)
O25	0.133 (2)	0.0310 (11)	0.0516 (13)	−0.0180 (12)	0.0519 (14)	−0.0163 (10)
C1	0.0184 (11)	0.0172 (10)	0.0114 (9)	0.0017 (9)	0.0074 (8)	0.0000 (8)
O22	0.0323 (10)	0.0226 (9)	0.0301 (9)	0.0005 (7)	0.0149 (8)	0.0082 (7)
O21	0.0329 (9)	0.0152 (8)	0.0325 (9)	0.0001 (7)	0.0192 (7)	0.0003 (7)
O24	0.0278 (9)	0.0200 (8)	0.0230 (8)	0.0023 (7)	0.0162 (7)	−0.0028 (6)
C5	0.0194 (11)	0.0283 (13)	0.0147 (10)	−0.0023 (10)	0.0068 (9)	0.0011 (9)
C7	0.0117 (11)	0.0166 (11)	0.0255 (11)	0.0006 (9)	0.0087 (9)	−0.0029 (9)
C19	0.0278 (13)	0.0297 (13)	0.0210 (11)	0.0034 (11)	0.0141 (10)	0.0075 (10)
C9	0.0195 (11)	0.0179 (12)	0.0179 (10)	−0.0009 (9)	0.0102 (9)	0.0021 (9)
C14	0.0192 (12)	0.0263 (12)	0.0143 (10)	−0.0013 (9)	0.0077 (9)	−0.0011 (9)
O23	0.0223 (8)	0.0191 (8)	0.0196 (7)	0.0027 (7)	0.0099 (6)	0.0010 (6)
N2	0.0177 (10)	0.0196 (10)	0.0146 (9)	0.0034 (7)	0.0071 (8)	−0.0009 (7)
C12	0.0116 (10)	0.0166 (11)	0.0162 (10)	−0.0018 (9)	0.0054 (8)	0.0007 (9)
C4A	0.0118 (11)	0.0240 (12)	0.0152 (10)	−0.0005 (9)	0.0059 (8)	−0.0002 (8)
C8A	0.0110 (11)	0.0181 (11)	0.0152 (10)	0.0015 (9)	0.0060 (8)	0.0003 (8)
C6	0.0151 (11)	0.0206 (12)	0.0200 (11)	0.0011 (9)	0.0069 (9)	0.0074 (9)
C10	0.0128 (11)	0.0165 (11)	0.0195 (10)	−0.0024 (8)	0.0076 (8)	0.0000 (8)
C11	0.0167 (11)	0.0205 (12)	0.0156 (10)	−0.0029 (9)	0.0076 (9)	−0.0001 (8)
C18	0.0362 (15)	0.0170 (12)	0.0346 (13)	0.0015 (10)	0.0201 (12)	0.0047 (10)
C16	0.0283 (13)	0.0172 (12)	0.0287 (12)	0.0048 (10)	0.0138 (10)	0.0036 (10)
C15	0.0201 (12)	0.0213 (12)	0.0166 (10)	0.0012 (9)	0.0089 (9)	0.0029 (9)
C20	0.0382 (14)	0.0315 (13)	0.0278 (12)	0.0022 (12)	0.0217 (11)	−0.0085 (11)
C8	0.0152 (11)	0.0232 (12)	0.0159 (10)	−0.0009 (9)	0.0093 (8)	−0.0014 (9)
C4	0.0287 (13)	0.0271 (14)	0.0180 (11)	−0.0016 (10)	0.0136 (10)	−0.0032 (9)
C17	0.0162 (11)	0.0274 (13)	0.0257 (11)	0.0017 (9)	0.0096 (9)	−0.0021 (9)
C13	0.0155 (11)	0.0171 (11)	0.0199 (11)	−0.0034 (9)	0.0086 (9)	−0.0036 (9)
C3	0.0192 (12)	0.0227 (12)	0.0175 (10)	−0.0007 (10)	0.0071 (9)	−0.0067 (9)

Geometric parameters (Å, º) top

Cl29—O25	1.406 (2)	N2—C16	1.488 (3)
Cl29—O26	1.4164 (18)	N2—C17	1.496 (3)
Cl29—O28	1.4211 (17)	N2—C3	1.504 (3)
Cl29—O27	1.4292 (17)	C12—C11	1.376 (3)
C1—C8A	1.510 (3)	C12—C13	1.404 (3)
C1—N2	1.526 (2)	C4A—C8A	1.383 (3)
C1—C9	1.533 (3)	C4A—C4	1.499 (3)
C1—H1A	1.000	C8A—C8	1.403 (3)
O22—C6	1.374 (2)	C10—C15	1.378 (3)
O22—C18	1.433 (3)	C10—C11	1.388 (3)
O21—C7	1.365 (2)	C11—H11A	0.950
O21—C18	1.425 (3)	C18—H18A	0.990
O24—C13	1.371 (2)	C18—H18B	0.990
O24—C20	1.421 (3)	C16—H16A	0.980
C5—C6	1.352 (3)	C16—H16B	0.980
C5—C4A	1.397 (3)	C16—H16C	0.980
C5—H5A	0.950	C15—H15A	0.950
C7—C8	1.364 (3)	C20—H20A	0.980
C7—C6	1.377 (3)	C20—H20B	0.980
C19—O23	1.420 (2)	C20—H20C	0.980
C19—H19A	0.980	C8—H8A	0.950
C19—H19B	0.980	C4—C3	1.507 (3)
C19—H19C	0.980	C4—H4A	0.990
C9—C10	1.500 (3)	C4—H4B	0.990
C9—H9A	0.990	C17—H17A	0.980
C9—H9B	0.990	C17—H17B	0.980
C14—C13	1.374 (3)	C17—H17C	0.980
C14—C15	1.388 (3)	C3—H3A	0.990
C14—H14A	0.950	C3—H3B	0.990
O23—C12	1.360 (2)

O25—Cl29—O26	110.65 (16)	C5—C6—C7	122.32 (19)
O25—Cl29—O28	109.40 (13)	O22—C6—C7	109.41 (18)
O26—Cl29—O28	108.54 (12)	C15—C10—C11	118.74 (19)
O25—Cl29—O27	109.67 (12)	C15—C10—C9	120.87 (18)
O26—Cl29—O27	108.38 (11)	C11—C10—C9	120.38 (17)
O28—Cl29—O27	110.17 (11)	C12—C11—C10	121.16 (18)
C8A—C1—N2	109.19 (15)	C12—C11—H11A	119.4
C8A—C1—C9	112.95 (17)	C10—C11—H11A	119.4
N2—C1—C9	111.74 (16)	O21—C18—O22	107.50 (17)
C8A—C1—H1A	107.6	O21—C18—H18A	110.2
N2—C1—H1A	107.6	O22—C18—H18A	110.2
C9—C1—H1A	107.6	O21—C18—H18B	110.2
C6—O22—C18	105.02 (15)	O22—C18—H18B	110.2
C7—O21—C18	105.11 (16)	H18A—C18—H18B	108.5
C13—O24—C20	116.54 (17)	N2—C16—H16A	109.5
C6—C5—C4A	117.70 (19)	N2—C16—H16B	109.5
C6—C5—H5A	121.2	H16A—C16—H16B	109.5
C4A—C5—H5A	121.2	N2—C16—H16C	109.5
C8—C7—O21	128.32 (18)	H16A—C16—H16C	109.5
C8—C7—C6	121.44 (19)	H16B—C16—H16C	109.5
O21—C7—C6	110.21 (18)	C10—C15—C14	120.94 (19)
O23—C19—H19A	109.5	C10—C15—H15A	119.5
O23—C19—H19B	109.5	C14—C15—H15A	119.5
H19A—C19—H19B	109.5	O24—C20—H20A	109.5
O23—C19—H19C	109.5	O24—C20—H20B	109.5
H19A—C19—H19C	109.5	H20A—C20—H20B	109.5
H19B—C19—H19C	109.5	O24—C20—H20C	109.5
C10—C9—C1	113.42 (17)	H20A—C20—H20C	109.5
C10—C9—H9A	108.9	H20B—C20—H20C	109.5
C1—C9—H9A	108.9	C7—C8—C8A	117.13 (18)
C10—C9—H9B	108.9	C7—C8—H8A	121.4
C1—C9—H9B	108.9	C8A—C8—H8A	121.4
H9A—C9—H9B	107.7	C4A—C4—C3	114.85 (17)
C13—C14—C15	120.00 (18)	C4A—C4—H4A	108.6
C13—C14—H14A	120.0	C3—C4—H4A	108.6
C15—C14—H14A	120.0	C4A—C4—H4B	108.6
C12—O23—C19	116.69 (16)	C3—C4—H4B	108.6
C16—N2—C17	107.30 (16)	H4A—C4—H4B	107.5
C16—N2—C3	108.72 (16)	N2—C17—H17A	109.5
C17—N2—C3	110.67 (16)	N2—C17—H17B	109.5
C16—N2—C1	111.43 (15)	H17A—C17—H17B	109.5
C17—N2—C1	108.78 (16)	N2—C17—H17C	109.5
C3—N2—C1	109.92 (16)	H17A—C17—H17C	109.5
O23—C12—C11	124.67 (17)	H17B—C17—H17C	109.5
O23—C12—C13	115.96 (17)	O24—C13—C14	124.60 (18)
C11—C12—C13	119.37 (18)	O24—C13—C12	115.73 (17)
C8A—C4A—C5	120.3 (2)	C14—C13—C12	119.66 (18)
C8A—C4A—C4	121.51 (19)	N2—C3—C4	112.33 (18)
C5—C4A—C4	118.00 (17)	N2—C3—H3A	109.1
C4A—C8A—C8	121.06 (19)	C4—C3—H3A	109.1
C4A—C8A—C1	121.58 (19)	N2—C3—H3B	109.1
C8—C8A—C1	117.30 (17)	C4—C3—H3B	109.1
C5—C6—O22	128.27 (18)	H3A—C3—H3B	107.9

C18—O21—C7—C8	−171.2 (2)	C1—C9—C10—C15	95.6 (2)
C18—O21—C7—C6	10.8 (2)	C1—C9—C10—C11	−85.1 (2)
C8A—C1—C9—C10	57.4 (2)	O23—C12—C11—C10	−176.16 (19)
N2—C1—C9—C10	−179.06 (15)	C13—C12—C11—C10	3.9 (3)
C8A—C1—N2—C16	177.27 (16)	C15—C10—C11—C12	−2.7 (3)
C9—C1—N2—C16	51.6 (2)	C9—C10—C11—C12	178.02 (18)
C8A—C1—N2—C17	−64.6 (2)	C7—O21—C18—O22	−16.4 (2)
C9—C1—N2—C17	169.68 (16)	C6—O22—C18—O21	15.9 (2)
C8A—C1—N2—C3	56.7 (2)	C11—C10—C15—C14	−0.5 (3)
C9—C1—N2—C3	−69.0 (2)	C9—C10—C15—C14	178.80 (19)
C19—O23—C12—C11	5.3 (3)	C13—C14—C15—C10	2.4 (3)
C19—O23—C12—C13	−174.79 (16)	O21—C7—C8—C8A	−176.3 (2)
C6—C5—C4A—C8A	1.3 (3)	C6—C7—C8—C8A	1.6 (3)
C6—C5—C4A—C4	176.2 (2)	C4A—C8A—C8—C7	−2.4 (3)
C5—C4A—C8A—C8	1.0 (3)	C1—C8A—C8—C7	174.71 (19)
C4—C4A—C8A—C8	−173.73 (19)	C8A—C4A—C4—C3	−10.6 (3)
C5—C4A—C8A—C1	−176.0 (2)	C5—C4A—C4—C3	174.57 (19)
C4—C4A—C8A—C1	9.3 (3)	C20—O24—C13—C14	4.5 (3)
N2—C1—C8A—C4A	−32.1 (3)	C20—O24—C13—C12	−176.64 (18)
C9—C1—C8A—C4A	92.9 (2)	C15—C14—C13—O24	177.65 (19)
N2—C1—C8A—C8	150.79 (17)	C15—C14—C13—C12	−1.2 (3)
C9—C1—C8A—C8	−84.2 (2)	O23—C12—C13—O24	−0.8 (3)
C4A—C5—C6—O22	177.6 (2)	C11—C12—C13—O24	179.15 (18)
C4A—C5—C6—C7	−2.2 (3)	O23—C12—C13—C14	178.14 (18)
C18—O22—C6—C5	170.8 (2)	C11—C12—C13—C14	−1.9 (3)
C18—O22—C6—C7	−9.4 (2)	C16—N2—C3—C4	177.06 (17)
C8—C7—C6—C5	0.8 (3)	C17—N2—C3—C4	59.5 (2)
O21—C7—C6—C5	179.0 (2)	C1—N2—C3—C4	−60.7 (2)
C8—C7—C6—O22	−179.08 (19)	C4A—C4—C3—N2	36.3 (3)
O21—C7—C6—O22	−0.9 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆NO₄⁺·ClO₄⁻
M_r	455.88
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	7.450 (1), 17.010 (3), 9.038 (2)
β (°)	114.32 (3)
V (Å³)	1043.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Kuma KM-4 CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6727, 3144, 3001
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.04
No. of reflections	3144
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20
Absolute structure	Flack (1983), 1276 Friedel pairs
Absolute structure parameter	−0.04 (5)

Computer programs: Xcalibur (Oxford Diffraction Ltd, 2001), Xcalibur, SHELXTL (Bruker, 1998), SHELXTL.

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