Acta Cryst. (2008). E64, o390 [ doi:10.1107/S1600536807068134 ]
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-HO hydrogen bond with a ClO4- anion. The crystal studied was an inversion twin.
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.
The H atoms of CH2 groups were refined in idealized geometrical positions with displacement parameters being equal to 1.2 times Ueq of the attached C atoms. The H atoms of NH2 were located on difference Fourier map and refined with displacement parameters being equal to 1.2 times Ueq of the attached N atoms and N—H distances restrained to 0.88 (1) Å.
The Flack parameter was explicitly refined. The absolute structure was selected on the basis of the lower Flack parameter; the structure is a racemic twin.
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).
![[Figure 1]](./ng2409fig1thm.gif)
| 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. |
![[Figure 2]](./ng2409fig2thm.gif)
| Fig. 2. The unit cell of (I). |
![[Figure 3]](./ng2409fig3thm.gif)
| Fig. 3. The comparison of two different types of chains. |
| 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 |
| C4H10NO+·ClO4– | V = 2248.41 (16) Å3 |
| Mr = 187.58 | Z = 12 |
| Orthorhombic, P212121 | Mo Kα |
| a = 8.1515 (3) Å | µ = 0.49 mm−1 |
| b = 9.5435 (4) Å | T = 100 (2) K |
| c = 28.9022 (12) Å | 0.24 × 0.20 × 0.16 mm |
| Bruker KappaAPEXII area-detector diffractometer | 6453 independent reflections |
| Absorption correction: none (SADABS; Sheldrick, 2004?) | 5928 reflections with I > 2σ(I) |
| 31159 measured reflections | Rint = 0.038 |
| R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.062 | Δρmax = 0.30 e Å−3 |
| S = 1.03 | Δρmin = −0.32 e Å−3 |
| 6453 reflections | Absolute structure: Flack (1983), 2793 Friedel pairs |
| 323 parameters | Flack parameter: 0.42 (3) |
| 6 restraints |
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) |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+3/2, −z+1. |
| 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. |
Bruker (1998). SAINT-Plus. Version 6.01. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Grigoriev, M. S., German, K. E. & Maruk, A. Y. (2007). Acta Cryst. E63, m2355–?.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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.