The cation and anion in the title salt, C6H22N44+·2SO42-·H2O, lie on special positions of site symmetry m and the water molecule on a special position of site symmetry 2/m. The cations, anions and water molecules are linked by hydrogen bonds into a three-dimensional network.
Supporting information
CCDC reference: 269394
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.070
- wR factor = 0.185
- Data-to-parameter ratio = 8.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.37
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 14.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT430_ALERT_2_C Short Inter D...A Contact O4 .. O4 .. 2.88 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Trimethylenetetraaminium(4+) bis(sulfate) monohydrate
top
Crystal data top
C6H22N44+·2SO42−·H2O | F(000) = 384 |
Mr = 360.41 | Dx = 1.550 Mg m−3 |
Orthorhombic, Pnnm | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2 2n | Cell parameters from 861 reflections |
a = 6.3192 (8) Å | θ = 3.4–23.5° |
b = 22.253 (3) Å | µ = 0.39 mm−1 |
c = 5.4903 (7) Å | T = 295 K |
V = 772.1 (2) Å3 | Block, yellow |
Z = 2 | 0.14 × 0.14 × 0.13 mm |
Data collection top
Bruker APEX area-detector diffractometer | 840 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 1.8° |
φ and ω scans | h = −8→3 |
3543 measured reflections | k = −25→28 |
946 independent reflections | l = −6→6 |
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0921P)2 + 1.2465P] where P = (Fo2 + 2Fc2)/3 |
946 reflections | (Δ/σ)max = 0.001 |
113 parameters | Δρmax = 0.57 e Å−3 |
148 restraints | Δρmin = −0.51 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.2004 (2) | 0.35894 (4) | 0.5000 | 0.0247 (4) | |
O1 | 0.360 (1) | 0.3110 (3) | 0.483 (4) | 0.034 (2) | 0.25 |
O2 | −0.0124 (9) | 0.3318 (3) | 0.472 (4) | 0.040 (3) | 0.25 |
O3 | 0.234 (3) | 0.4028 (5) | 0.306 (2) | 0.039 (4) | 0.25 |
O4 | 0.215 (3) | 0.3881 (6) | 0.7382 (16) | 0.033 (3) | 0.25 |
O5 | 0.156 (3) | 0.3167 (7) | 0.301 (2) | 0.027 (3) | 0.25 |
O6 | 0.4171 (9) | 0.3820 (3) | 0.474 (4) | 0.045 (3) | 0.25 |
O7 | 0.178 (3) | 0.3280 (8) | 0.735 (2) | 0.032 (4) | 0.25 |
O8 | 0.049 (1) | 0.4091 (2) | 0.488 (5) | 0.036 (2) | 0.25 |
O1W | 0.5000 | 0.5000 | 0.5000 | 0.160 (5) | |
N1 | 0.5074 (6) | 0.29452 (16) | 0.0000 | 0.0324 (9) | |
N2 | 0.8959 (6) | 0.42124 (15) | 0.0000 | 0.0302 (9) | |
C1 | 0.7079 (8) | 0.3255 (2) | 0.0000 | 0.044 (1) | |
C2 | 0.6924 (7) | 0.3914 (2) | 0.0000 | 0.039 (1) | |
C3 | 0.8940 (7) | 0.48638 (19) | 0.0000 | 0.039 (1) | |
H1W1 | 0.5946 | 0.5260 | 0.4685 | 0.192* | 0.25 |
H1W2 | 0.5269 | 0.4676 | 0.4242 | 0.192* | 0.25 |
H1N1 | 0.5288 | 0.2564 | 0.0000 | 0.039* | |
H1N2 | 0.4369 | 0.3044 | 0.1279 | 0.039* | |
H2N | 0.9650 | 0.4094 | −0.1262 | 0.036* | |
H1 | 0.7874 | 0.3131 | 0.1425 | 0.053* | |
H2 | 0.6135 | 0.4040 | 0.1427 | 0.047* | |
H3 | 0.8177 | 0.5002 | 0.1426 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0245 (6) | 0.0217 (6) | 0.0278 (6) | −0.0004 (4) | 0.000 | 0.000 |
O1 | 0.041 (4) | 0.033 (3) | 0.027 (6) | 0.013 (3) | 0.004 (7) | 0.000 (6) |
O2 | 0.036 (4) | 0.040 (4) | 0.044 (8) | −0.006 (3) | −0.020 (6) | 0.011 (5) |
O3 | 0.049 (7) | 0.033 (7) | 0.036 (6) | −0.005 (5) | 0.002 (5) | 0.008 (5) |
O4 | 0.033 (5) | 0.035 (6) | 0.033 (6) | 0.002 (5) | −0.004 (5) | −0.005 (5) |
O5 | 0.030 (6) | 0.020 (6) | 0.030 (6) | −0.010 (4) | 0.005 (5) | −0.007 (5) |
O6 | 0.038 (4) | 0.046 (4) | 0.051 (8) | −0.013 (3) | 0.017 (6) | −0.003 (6) |
O7 | 0.032 (7) | 0.034 (7) | 0.030 (6) | 0.001 (5) | 0.007 (5) | −0.002 (5) |
O8 | 0.051 (4) | 0.026 (3) | 0.032 (5) | 0.012 (3) | −0.009 (8) | −0.001 (8) |
O1W | 0.162 (8) | 0.120 (7) | 0.198 (9) | −0.068 (6) | 0.000 | 0.000 |
N1 | 0.029 (2) | 0.021 (2) | 0.047 (2) | 0.002 (2) | 0.000 | 0.000 |
N2 | 0.024 (2) | 0.022 (2) | 0.045 (2) | 0.002 (2) | 0.000 | 0.000 |
C1 | 0.025 (2) | 0.025 (2) | 0.081 (4) | 0.002 (2) | 0.000 | 0.000 |
C2 | 0.024 (2) | 0.023 (2) | 0.071 (4) | 0.000 (2) | 0.000 | 0.000 |
C3 | 0.028 (2) | 0.020 (2) | 0.069 (4) | 0.003 (2) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
S1—O1 | 1.470 (5) | C1—C2 | 1.469 (7) |
S1—O2 | 1.482 (6) | C3—C3i | 1.470 (9) |
S1—O3 | 1.461 (6) | O1W—H1W1 | 0.85 |
S1—O4 | 1.463 (6) | O1W—H1W2 | 0.85 |
S1—O5 | 1.471 (6) | N1—H1N1 | 0.86 |
S1—O6 | 1.469 (5) | N1—H1N2 | 0.86 |
S1—O7 | 1.468 (7) | N2—H2N | 0.86 |
S1—O8 | 1.472 (5) | C1—H1 | 0.97 |
N1—C1 | 1.443 (6) | C2—H2 | 0.97 |
N2—C2 | 1.448 (6) | C3—H3 | 0.97 |
N2—C3 | 1.450 (5) | | |
| | | |
O1—S1—O2 | 108.6 (5) | N2—C2—C1 | 113.5 (4) |
O1—S1—O3 | 109.9 (5) | N2—C3—C3i | 113.9 (5) |
O1—S1—O4 | 109.7 (5) | H1W1—O1W—H1W2 | 109.7 |
O2—S1—O3 | 109.2 (5) | C1—N1—H1N1 | 109.5 |
O2—S1—O4 | 109.2 (5) | C1—N1—H1N2 | 109.5 |
O3—S1—O4 | 110.3 (4) | H1N1—N1—H1N2 | 109.5 |
O5—S1—O6 | 109.4 (5) | C2—N2—H2N | 108.1 |
O5—S1—O7 | 109.6 (4) | C3—N2—H2N | 108.1 |
O5—S1—O8 | 109.1 (5) | N1—C1—H1 | 108.6 |
O6—S1—O7 | 109.8 (5) | C2—C1—H1 | 108.6 |
O6—S1—O8 | 109.8 (5) | N2—C2—H2 | 108.9 |
O7—S1—O8 | 109.7 (5) | C1—C2—H2 | 108.9 |
C2—N2—C3 | 116.9 (4) | N2—C3—H3 | 108.8 |
N1—C1—C2 | 114.7 (4) | C3i—C3—H3 | 108.8 |
| | | |
C3—N2—C2—C1 | 180.0 | C2—N2—C3—C3i | 180.0 |
N1—C1—C2—N2 | 180.0 | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O3ii | 0.85 | 2.29 | 2.94 (1) | 134 |
O1W—H1W1···O3iii | 0.85 | 2.12 | 2.94 (1) | 163 |
O1W—H1W2···O6 | 0.85 | 2.05 | 2.681 (7) | 131 |
O1W—H1W2···O6iv | 0.85 | 2.10 | 2.681 (7) | 125 |
O1W—H1W1···O6ii | 0.85 | 2.07 | 2.681 (7) | 128 |
O1W—H1W1···O6iii | 0.85 | 2.05 | 2.681 (7) | 131 |
N1—H1N1···O2v | 0.86 | 1.98 | 2.818 (8) | 163 |
N1—H1N1···O5v | 0.86 | 2.12 | 2.86 (2) | 145 |
N1—H1N2···O1 | 0.86 | 2.01 | 2.83 (2) | 159 |
N1—H1N2···O7iv | 0.86 | 1.88 | 2.65 (2) | 148 |
N2—H2N···O3vi | 0.86 | 1.97 | 2.75 (2) | 150 |
N2—H2N···O4vii | 0.86 | 1.81 | 2.58 (2) | 149 |
N2—H2N···O7vii | 0.86 | 2.38 | 3.10 (2) | 141 |
N2—H2N···O8vi | 0.86 | 2.06 | 2.86 (3) | 156 |
N2—H2N···O8vii | 0.86 | 2.18 | 2.98 (3) | 155 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, z; (iv) x, y, −z+1; (v) x+1/2, −y+1/2, −z+1/2; (vi) x+1, y, −z; (vii) x+1, y, z−1. |