Morpholinium perchlorate.

In the title salt, C(4)H(10)NO(+)·ClO(4) (-), 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 ClO(4) (-) 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 = 187.58

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.062

S = 1.03

6453 reflections

323 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

Absolute structure: Flack (1983 ▶), 2793 Friedel pairs

Flack parameter: 0.42 (3)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H10NO+·ClO4–	F000 = 1176
Mr = 187.58	Dx = 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 = 2.3–30.0º
b = 9.5435 (4) Å	µ = 0.49 mm−1
c = 28.9022 (12) Å	T = 100 (2) K
V = 2248.41 (16) Å3	Fragment, colourless
Z = 12	0.24 × 0.20 × 0.16 mm

Bruker KappaAPEXII area-detector diffractometer	5928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Monochromator: graphite	θmax = 30.0º
T = 100(2) K	θmin = 2.3º
ω and φ scans	h = −11→11
Absorption correction: none (SADABS; Sheldrick, 2004?)	k = −13→13
31159 measured reflections	l = −40→40
6453 independent reflections

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.025	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.062	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.30 e Å−3
6453 reflections	Δρmin = −0.32 e Å−3
323 parameters	Extinction correction: none
6 restraints	Absolute structure: Flack (1983), 2793 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.42 (3)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .