Morpholinium perchlorate

Grigoriev, M.S.; German, K.E.; Maruk, A.Y.

doi:10.1107/S1600536807068134

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o390

doi:10.1107/S1600536807068134

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Morpholinium perchlorate

Mikhail S. Grigoriev,^a ^* Konstantin E. German ^a and Alesia Ya. Maruk ^a

^aA. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 31 Leninsky prospekt, 119991 Moscow, Russian Federation
^*Correspondence e-mail: grigoriev@ipc.rssi.ru

(Received 11 December 2007; accepted 21 December 2007; online 9 January 2008)

In the title salt, C₄H₁₀NO⁺·ClO₄⁻, which has three independent formula units, the cations are linked into chains along [100] by N—H⋯O hydrogen bonds. Each cation acts both as a donor and as an acceptor, and every cation makes one N—H⋯O hydrogen bond with a ClO₄⁻ anion. The crystal studied was an inversion twin.

Related literature

See Grigoriev et al. (2007 ) for the structure of morpholinium tetraoxidorhenate(VII).

Experimental

Crystal data

C₄H₁₀NO⁺·ClO₄⁻
M_r = 187.58
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.1515 (3) Å
b = 9.5435 (4) Å
c = 28.9022 (12) Å
V = 2248.41 (16) Å³
Z = 12
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 100 (2) K
0.24 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: none
31159 measured reflections
6453 independent reflections
5928 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.062
S = 1.03
6453 reflections
323 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ), 2793 Friedel pairs
Flack parameter: 0.42 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2	0.877 (9)	2.051 (13)	2.7872 (16)	141.0 (15)
N1—H1D⋯O15ⁱ	0.871 (9)	2.015 (10)	2.8642 (15)	164.7 (16)
N2—H2C⋯O14ⁱⁱ	0.884 (9)	1.980 (10)	2.8441 (14)	165.5 (16)
N2—H2D⋯O8	0.889 (9)	2.020 (11)	2.8465 (15)	154.1 (15)
N3—H3C⋯O13ⁱ	0.878 (9)	2.004 (10)	2.8690 (15)	168.0 (17)
N3—H3D⋯O9	0.870 (9)	2.039 (13)	2.7895 (17)	143.9 (16)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT-Plus (Bruker, 1998 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068134/ng2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068134/ng2409Isup2.hkl

checkCIF report

Comment top

The title compound, (I) (Fig. 1), contains slightly distorted tetrahedral ClO₄^- anions with Cl—O distances from 1.4353 (11) to 1.4496 (10) Å. Morpholinium cations have chair conformation.

The structure of (I) can be described as alternating cationic and anionic layers parallel to the (013) plane (Fig. 2).

Every morpholinium cation acts as proton donor in two hydrogen bonds, acceptors being O atoms of another morpholinium cation and ClO₄^- anion (Fig. 3, Table 1).

Morpholinium tetraoxidochlorate(VII) contains three independent formula units, which make two different types of zigzag chains in the [100] direction by N—H···O hydrogen bonds between cations (Fig. 3). The first type is formed by one formula unit and the second type is formed by two remaining formula units. As it is nseen in Fig. 3, two types of chains have different orientation of ClO₄^- anions.

The structure of morpholinium tetraoxidorhenate(VII) (Grigoriev et al., 2007) also contains alternating cationic and anionic layers with hydrogen bonds in perpendicular direction. But in contrast to (I), O atoms of morpholinium in (C₄H₁₀NO)[ReO₄] do not participate in hydrogen-bonding.

Related literature top

See Grigoriev et al. (2007) for the structure of morpholinium perrhenatetetraoxidorhenate.

For related literature, see: Sheldrick (2004).

Experimental top

Synthesis of (I) was carried out as a neutralization reaction by dissolution of stoichiometric quantity of morpholine under intensive stirring in 0.92 M water solution of HClO₄ at room temperature, followed by evaporation of the resulting solution at temperature 323 K.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. A view of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented by circles of arbitrary size. Dashed lines indicate the hydrogen-bonding interaction.
	Fig. 2. The unit cell of (I).
	Fig. 3. The comparison of two different types of chains.

Morpholinium perchlorate top

Crystal data top

C₄H₁₀NO⁺·ClO₄⁻	F(000) = 1176
M_r = 187.58	D_x = 1.662 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7054 reflections
a = 8.1515 (3) Å	θ = 2.3–30.0°
b = 9.5435 (4) Å	µ = 0.49 mm⁻¹
c = 28.9022 (12) Å	T = 100 K
V = 2248.41 (16) Å³	Fragment, colourless
Z = 12	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker KappaAPEXII area-detector diffractometer	5928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 30.0°, θ_min = 2.3°
ω and ϕ scans	h = −11→11
31159 measured reflections	k = −13→13
6453 independent reflections	l = −40→40

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.062	w = 1/[σ²(F_o²) + (0.0368P)² + 0.1234P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6453 reflections	Δρ_max = 0.30 e Å⁻³
323 parameters	Δρ_min = −0.32 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 2793 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.42 (3)

Crystal data top

C₄H₁₀NO⁺·ClO₄⁻	V = 2248.41 (16) Å³
M_r = 187.58	Z = 12
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.1515 (3) Å	µ = 0.49 mm⁻¹
b = 9.5435 (4) Å	T = 100 K
c = 28.9022 (12) Å	0.24 × 0.20 × 0.16 mm

Data collection top

Bruker KappaAPEXII area-detector diffractometer	5928 reflections with I > 2σ(I)
31159 measured reflections	R_int = 0.038
6453 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.062	Δρ_max = 0.30 e Å⁻³
S = 1.03	Δρ_min = −0.32 e Å⁻³
6453 reflections	Absolute structure: Flack (1983), 2793 Friedel pairs
323 parameters	Absolute structure parameter: 0.42 (3)
6 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
Cl1	0.57617 (4)	−0.38371 (3)	0.659062 (11)	0.01229 (6)
Cl2	0.37184 (4)	0.16395 (3)	0.506534 (10)	0.01225 (6)
Cl3	0.57257 (4)	−0.35661 (3)	0.339378 (11)	0.01296 (7)
O1	0.68287 (14)	−0.37350 (14)	0.69869 (4)	0.0261 (3)
O2	0.53026 (15)	−0.24599 (12)	0.64345 (5)	0.0297 (3)
O3	0.43207 (14)	−0.46173 (11)	0.67131 (4)	0.0207 (2)
O4	0.66220 (12)	−0.45314 (11)	0.62201 (3)	0.0157 (2)
O5	0.34519 (14)	0.23379 (12)	0.46318 (4)	0.0237 (2)
O6	0.22474 (13)	0.09516 (12)	0.52183 (4)	0.0246 (2)
O7	0.50117 (12)	0.06236 (11)	0.50191 (4)	0.0248 (2)
O8	0.41766 (13)	0.26762 (11)	0.54084 (4)	0.0189 (2)
O9	0.53099 (16)	−0.22094 (13)	0.35767 (5)	0.0342 (3)
O10	0.67421 (14)	−0.34228 (16)	0.29901 (4)	0.0321 (3)
O11	0.42568 (14)	−0.43179 (12)	0.32752 (4)	0.0236 (2)
O12	0.66235 (13)	−0.43202 (11)	0.37422 (3)	0.0168 (2)
O13	0.69481 (11)	0.24689 (11)	0.67280 (4)	0.0155 (2)
O14	0.22067 (11)	0.76837 (11)	0.49220 (3)	0.0171 (2)
O15	0.69469 (12)	0.27281 (11)	0.32867 (4)	0.0165 (2)
N1	0.45845 (14)	0.02905 (12)	0.66878 (4)	0.0119 (2)
H1C	0.434 (2)	−0.0603 (10)	0.6668 (6)	0.014*
H1D	0.3666 (14)	0.0755 (16)	0.6699 (6)	0.014*
N2	0.44656 (13)	0.54724 (12)	0.50755 (4)	0.0135 (2)
H2C	0.5419 (14)	0.5912 (16)	0.5086 (6)	0.016*
H2D	0.462 (2)	0.4558 (10)	0.5114 (6)	0.016*
N3	0.45865 (14)	0.05497 (12)	0.33319 (4)	0.0122 (2)
H3C	0.3684 (15)	0.1049 (17)	0.3313 (6)	0.015*
H3D	0.440 (2)	−0.0347 (10)	0.3344 (6)	0.015*
C1	0.55582 (18)	0.05548 (15)	0.71163 (5)	0.0144 (3)
H1A	0.492 (2)	0.0284 (19)	0.7388 (6)	0.017*
H1B	0.646 (2)	0.0006 (19)	0.7113 (6)	0.017*
C2	0.60347 (17)	0.20873 (15)	0.71312 (5)	0.0164 (3)
H2A	0.5033	0.2671	0.7151	0.020*
H2B	0.6705	0.2268	0.7411	0.020*
C3	0.59875 (17)	0.22590 (15)	0.63150 (5)	0.0143 (3)
H3A	0.6628	0.2556	0.6041	0.017*
H3B	0.4981	0.2838	0.6330	0.017*
C4	0.55258 (18)	0.07310 (14)	0.62683 (5)	0.0144 (3)
H4A	0.4847	0.0594	0.5988	0.017*
H4B	0.6528	0.0153	0.6237	0.017*
C5	0.33638 (17)	0.60033 (17)	0.54496 (5)	0.0167 (3)
H5A	0.3905	0.5894	0.5754	0.020*
H5B	0.2331	0.5458	0.5453	0.020*
C6	0.29959 (18)	0.75241 (16)	0.53623 (5)	0.0188 (3)
H6A	0.2273	0.7889	0.5610	0.023*
H6B	0.4028	0.8070	0.5367	0.023*
C7	0.32779 (17)	0.72437 (16)	0.45577 (5)	0.0164 (3)
H7A	0.4293	0.7813	0.4564	0.020*
H7B	0.2736	0.7395	0.4255	0.020*
C8	0.37108 (18)	0.57105 (15)	0.46105 (4)	0.0148 (3)
H8A	0.2710	0.5131	0.4578	0.018*
H8B	0.4492	0.5431	0.4365	0.018*
C9	0.55216 (18)	0.10032 (15)	0.37512 (4)	0.0150 (3)
H9A	0.6521	0.0423	0.3786	0.018*
H9B	0.4837	0.0879	0.4031	0.018*
C10	0.59916 (17)	0.25284 (15)	0.36984 (5)	0.0162 (3)
H10A	0.4988	0.3110	0.3682	0.019*
H10B	0.6634	0.2832	0.3971	0.019*
C11	0.60345 (17)	0.23347 (15)	0.28832 (5)	0.0168 (3)
H11A	0.6704	0.2510	0.2603	0.020*
H11B	0.5029	0.2913	0.2862	0.020*
C12	0.55698 (18)	0.07970 (14)	0.29050 (5)	0.0146 (3)
H12A	0.4920	0.0539	0.2629	0.018*
H12B	0.6572	0.0211	0.2911	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01222 (14)	0.01077 (13)	0.01386 (13)	−0.00072 (11)	0.00049 (11)	−0.00074 (11)
Cl2	0.01095 (11)	0.01167 (13)	0.01412 (13)	0.00027 (10)	−0.00132 (11)	−0.00073 (11)
Cl3	0.01248 (14)	0.01263 (14)	0.01377 (13)	−0.00160 (11)	−0.00006 (11)	0.00151 (11)
O1	0.0178 (5)	0.0441 (8)	0.0165 (5)	−0.0076 (5)	−0.0015 (4)	−0.0063 (5)
O2	0.0395 (7)	0.0108 (5)	0.0389 (7)	0.0094 (5)	0.0117 (5)	0.0024 (5)
O3	0.0130 (4)	0.0230 (5)	0.0262 (5)	−0.0054 (4)	0.0027 (4)	0.0000 (4)
O4	0.0170 (5)	0.0146 (5)	0.0155 (4)	0.0036 (4)	0.0009 (4)	−0.0010 (4)
O5	0.0302 (6)	0.0260 (6)	0.0150 (5)	0.0064 (5)	−0.0028 (4)	0.0020 (4)
O6	0.0154 (5)	0.0216 (6)	0.0368 (6)	−0.0073 (4)	0.0043 (4)	−0.0036 (5)
O7	0.0189 (5)	0.0193 (5)	0.0361 (6)	0.0093 (4)	0.0022 (5)	0.0007 (5)
O8	0.0271 (5)	0.0143 (5)	0.0153 (5)	−0.0058 (4)	−0.0048 (4)	−0.0006 (4)
O9	0.0453 (8)	0.0124 (5)	0.0449 (8)	0.0121 (5)	−0.0133 (6)	−0.0033 (5)
O10	0.0233 (6)	0.0579 (9)	0.0150 (5)	−0.0133 (6)	0.0023 (4)	0.0081 (6)
O11	0.0126 (5)	0.0272 (6)	0.0311 (6)	−0.0067 (4)	−0.0034 (4)	0.0013 (5)
O12	0.0195 (5)	0.0152 (5)	0.0158 (4)	0.0042 (4)	−0.0018 (4)	0.0001 (4)
O13	0.0128 (4)	0.0172 (5)	0.0166 (5)	−0.0049 (4)	−0.0022 (4)	0.0006 (4)
O14	0.0143 (4)	0.0174 (5)	0.0196 (5)	0.0057 (4)	−0.0010 (4)	−0.0015 (4)
O15	0.0129 (5)	0.0185 (5)	0.0181 (5)	−0.0061 (4)	0.0007 (4)	−0.0014 (4)
N1	0.0104 (5)	0.0102 (5)	0.0152 (5)	0.0001 (4)	−0.0003 (4)	−0.0012 (4)
N2	0.0108 (5)	0.0101 (5)	0.0195 (6)	0.0003 (4)	−0.0001 (4)	0.0018 (4)
N3	0.0115 (6)	0.0092 (5)	0.0159 (5)	0.0000 (4)	0.0008 (4)	0.0014 (4)
C1	0.0158 (7)	0.0162 (7)	0.0112 (6)	−0.0004 (5)	−0.0004 (5)	0.0012 (5)
C2	0.0180 (7)	0.0167 (7)	0.0145 (6)	−0.0036 (5)	−0.0015 (5)	−0.0027 (5)
C3	0.0163 (7)	0.0131 (6)	0.0133 (6)	−0.0010 (5)	−0.0013 (5)	0.0009 (5)
C4	0.0187 (7)	0.0127 (6)	0.0118 (6)	0.0001 (5)	−0.0002 (5)	−0.0013 (5)
C5	0.0146 (6)	0.0244 (7)	0.0109 (5)	−0.0002 (5)	0.0002 (5)	0.0009 (5)
C6	0.0183 (7)	0.0210 (8)	0.0170 (7)	0.0030 (5)	−0.0020 (5)	−0.0072 (6)
C7	0.0159 (6)	0.0181 (7)	0.0152 (6)	0.0024 (5)	0.0017 (5)	0.0045 (5)
C8	0.0166 (6)	0.0156 (7)	0.0123 (6)	0.0012 (5)	0.0026 (5)	−0.0010 (5)
C9	0.0174 (7)	0.0180 (7)	0.0097 (5)	0.0004 (5)	0.0004 (5)	0.0014 (5)
C10	0.0169 (7)	0.0156 (7)	0.0161 (6)	−0.0014 (5)	0.0009 (5)	−0.0024 (5)
C11	0.0169 (7)	0.0185 (7)	0.0150 (6)	−0.0038 (5)	0.0000 (5)	0.0031 (5)
C12	0.0156 (6)	0.0167 (7)	0.0116 (6)	−0.0013 (5)	0.0011 (5)	−0.0009 (5)

Geometric parameters (Å, º) top

Cl1—O3	1.4351 (11)	C1—C2	1.514 (2)
Cl1—O2	1.4391 (12)	C1—H1A	0.975 (18)
Cl1—O4	1.4415 (10)	C1—H1B	0.900 (18)
Cl1—O1	1.4415 (11)	C2—H2A	0.9900
Cl2—O5	1.4359 (11)	C2—H2B	0.9900
Cl2—O6	1.4367 (11)	C3—C4	1.5121 (19)
Cl2—O7	1.4385 (10)	C3—H3A	0.9900
Cl2—O8	1.4496 (10)	C3—H3B	0.9900
Cl3—O11	1.4374 (11)	C4—H4A	0.9900
Cl3—O10	1.4376 (11)	C4—H4B	0.9900
Cl3—O12	1.4379 (10)	C5—C6	1.503 (2)
Cl3—O9	1.4390 (13)	C5—H5A	0.9900
O13—C2	1.4301 (17)	C5—H5B	0.9900
O13—C3	1.4415 (16)	C6—H6A	0.9900
O14—C7	1.4308 (16)	C6—H6B	0.9900
O14—C6	1.4342 (17)	C7—C8	1.513 (2)
O15—C11	1.4333 (17)	C7—H7A	0.9900
O15—C10	1.4349 (17)	C7—H7B	0.9900
N1—C1	1.4926 (17)	C8—H8A	0.9900
N1—C4	1.4951 (17)	C8—H8B	0.9900
N1—H1C	0.877 (9)	C9—C10	1.513 (2)
N1—H1D	0.871 (9)	C9—H9A	0.9900
N2—C5	1.4943 (18)	C9—H9B	0.9900
N2—C8	1.4955 (17)	C10—H10A	0.9900
N2—H2C	0.884 (9)	C10—H10B	0.9900
N2—H2D	0.889 (9)	C11—C12	1.5169 (19)
N3—C12	1.4903 (17)	C11—H11A	0.9900
N3—C9	1.4956 (18)	C11—H11B	0.9900
N3—H3C	0.878 (9)	C12—H12A	0.9900
N3—H3D	0.870 (9)	C12—H12B	0.9900

O3—Cl1—O2	109.78 (7)	H3A—C3—H3B	108.2
O3—Cl1—O4	110.06 (6)	N1—C4—C3	109.05 (11)
O2—Cl1—O4	108.26 (7)	N1—C4—H4A	109.9
O3—Cl1—O1	109.45 (7)	C3—C4—H4A	109.9
O2—Cl1—O1	110.14 (8)	N1—C4—H4B	109.9
O4—Cl1—O1	109.14 (7)	C3—C4—H4B	109.9
O5—Cl2—O6	110.75 (7)	H4A—C4—H4B	108.3
O5—Cl2—O7	110.04 (7)	N2—C5—C6	109.01 (12)
O6—Cl2—O7	109.41 (7)	N2—C5—H5A	109.9
O5—Cl2—O8	108.60 (7)	C6—C5—H5A	109.9
O6—Cl2—O8	108.45 (7)	N2—C5—H5B	109.9
O7—Cl2—O8	109.55 (7)	C6—C5—H5B	109.9
O11—Cl3—O10	109.51 (7)	H5A—C5—H5B	108.3
O11—Cl3—O12	109.94 (7)	O14—C6—C5	109.94 (12)
O10—Cl3—O12	108.83 (7)	O14—C6—H6A	109.7
O11—Cl3—O9	109.91 (8)	C5—C6—H6A	109.7
O10—Cl3—O9	110.39 (9)	O14—C6—H6B	109.7
O12—Cl3—O9	108.24 (7)	C5—C6—H6B	109.7
C2—O13—C3	110.89 (10)	H6A—C6—H6B	108.2
C7—O14—C6	110.37 (10)	O14—C7—C8	110.61 (11)
C11—O15—C10	111.00 (10)	O14—C7—H7A	109.5
C1—N1—C4	110.64 (10)	C8—C7—H7A	109.5
C1—N1—H1C	109.7 (11)	O14—C7—H7B	109.5
C4—N1—H1C	109.6 (11)	C8—C7—H7B	109.5
C1—N1—H1D	109.9 (11)	H7A—C7—H7B	108.1
C4—N1—H1D	109.2 (11)	N2—C8—C7	109.49 (11)
H1C—N1—H1D	107.8 (16)	N2—C8—H8A	109.8
C5—N2—C8	110.58 (10)	C7—C8—H8A	109.8
C5—N2—H2C	110.1 (11)	N2—C8—H8B	109.8
C8—N2—H2C	108.7 (11)	C7—C8—H8B	109.8
C5—N2—H2D	109.2 (11)	H8A—C8—H8B	108.2
C8—N2—H2D	108.7 (11)	N3—C9—C10	109.02 (11)
H2C—N2—H2D	109.6 (15)	N3—C9—H9A	109.9
C12—N3—C9	110.54 (11)	C10—C9—H9A	109.9
C12—N3—H3C	108.1 (11)	N3—C9—H9B	109.9
C9—N3—H3C	108.8 (11)	C10—C9—H9B	109.9
C12—N3—H3D	106.5 (11)	H9A—C9—H9B	108.3
C9—N3—H3D	109.9 (12)	O15—C10—C9	110.41 (11)
H3C—N3—H3D	113.0 (17)	O15—C10—H10A	109.6
N1—C1—C2	108.86 (11)	C9—C10—H10A	109.6
N1—C1—H1A	109.9 (10)	O15—C10—H10B	109.6
C2—C1—H1A	111.7 (11)	C9—C10—H10B	109.6
N1—C1—H1B	109.0 (11)	H10A—C10—H10B	108.1
C2—C1—H1B	110.8 (12)	O15—C11—C12	110.44 (12)
H1A—C1—H1B	106.5 (15)	O15—C11—H11A	109.6
O13—C2—C1	110.88 (11)	C12—C11—H11A	109.6
O13—C2—H2A	109.5	O15—C11—H11B	109.6
C1—C2—H2A	109.5	C12—C11—H11B	109.6
O13—C2—H2B	109.5	H11A—C11—H11B	108.1
C1—C2—H2B	109.5	N3—C12—C11	108.78 (11)
H2A—C2—H2B	108.1	N3—C12—H12A	109.9
O13—C3—C4	110.07 (11)	C11—C12—H12A	109.9
O13—C3—H3A	109.6	N3—C12—H12B	109.9
C4—C3—H3A	109.6	C11—C12—H12B	109.9
O13—C3—H3B	109.6	H12A—C12—H12B	108.3
C4—C3—H3B	109.6

C4—N1—C1—C2	56.08 (15)	C6—O14—C7—C8	61.45 (14)
C3—O13—C2—C1	60.92 (15)	C5—N2—C8—C7	54.51 (14)
N1—C1—C2—O13	−57.76 (15)	O14—C7—C8—N2	−56.81 (14)
C2—O13—C3—C4	−61.05 (15)	C12—N3—C9—C10	56.67 (14)
C1—N1—C4—C3	−56.79 (15)	C11—O15—C10—C9	60.83 (14)
O13—C3—C4—N1	58.36 (14)	N3—C9—C10—O15	−57.92 (14)
C8—N2—C5—C6	−56.06 (14)	C10—O15—C11—C12	−61.04 (14)
C7—O14—C6—C5	−62.99 (15)	C9—N3—C12—C11	−56.71 (15)
N2—C5—C6—O14	59.76 (15)	O15—C11—C12—N3	58.34 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.88 (1)	2.05 (1)	2.7872 (16)	141 (2)
N1—H1D···O15ⁱ	0.87 (1)	2.02 (1)	2.8642 (15)	165 (2)
N2—H2C···O14ⁱⁱ	0.88 (1)	1.98 (1)	2.8441 (14)	166 (2)
N2—H2D···O8	0.89 (1)	2.02 (1)	2.8465 (15)	154 (2)
N3—H3C···O13ⁱ	0.88 (1)	2.00 (1)	2.8690 (15)	168 (2)
N3—H3D···O9	0.87 (1)	2.04 (1)	2.7895 (17)	144 (2)

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

Experimental details

Crystal data
Chemical formula	C₄H₁₀NO⁺·ClO₄⁻
M_r	187.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.1515 (3), 9.5435 (4), 28.9022 (12)
V (Å³)	2248.41 (16)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.24 × 0.20 × 0.16

Data collection
Diffractometer	Bruker KappaAPEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	31159, 6453, 5928
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.062, 1.03
No. of reflections	6453
No. of parameters	323
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32
Absolute structure	Flack (1983), 2793 Friedel pairs
Absolute structure parameter	0.42 (3)

Computer programs: APEX2 (Bruker, 2006), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.877 (9)	2.051 (13)	2.7872 (16)	141.0 (15)
N1—H1D···O15ⁱ	0.871 (9)	2.015 (10)	2.8642 (15)	164.7 (16)
N2—H2C···O14ⁱⁱ	0.884 (9)	1.980 (10)	2.8441 (14)	165.5 (16)
N2—H2D···O8	0.889 (9)	2.020 (11)	2.8465 (15)	154.1 (15)
N3—H3C···O13ⁱ	0.878 (9)	2.004 (10)	2.8690 (15)	168.0 (17)
N3—H3D···O9	0.870 (9)	2.039 (13)	2.7895 (17)	143.9 (16)

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

References

Bruker (1998). SAINT-Plus. Version 6.01. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2006). APEX2. 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
Grigoriev, M. S., German, K. E. & Maruk, A. Y. (2007). Acta Cryst. E63, m2355. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 2| February 2008| Page o390

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