The buffer reagent piperazine-1,4-diylbis(2-hydroxypropanesulfonic acid) (PBHPS), when crystallized from an aqueous solution, exists as the title centrosymmetric hydrated zwitterion, C10H22N2O8S2·2H2O. The zwitterion and solvent water molecules are linked by hydrogen bonds into a three-dimensional network.
Supporting information
CCDC reference: 618351
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.099
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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.
2,2'-Dihydroxy-3,3'-(piperazinediium-1,4-diyl)bis(propanesulfonate) dihydrate
top
Crystal data top
C10H22N2O8S2·2H2O | F(000) = 424 |
Mr = 398.45 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1706 reflections |
a = 8.6675 (8) Å | θ = 3.0–27.5° |
b = 7.2050 (6) Å | µ = 0.38 mm−1 |
c = 13.198 (1) Å | T = 291 K |
β = 96.859 (1)° | Block, colourless |
V = 818.31 (12) Å3 | 0.21 × 0.14 × 0.05 mm |
Z = 2 | |
Data collection top
Bruker APEXII area-detector diffractometer | 1551 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
φ and ω scans | h = −11→11 |
4919 measured reflections | k = −8→9 |
1865 independent reflections | l = −15→17 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.5041P] where P = (Fo2 + 2Fc2)/3 |
1865 reflections | (Δ/σ)max = 0.001 |
125 parameters | Δρmax = 0.38 e Å−3 |
4 restraints | Δρmin = −0.24 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | −0.06801 (5) | 1.06546 (7) | 0.32225 (4) | 0.0247 (2) | |
O1 | −0.0529 (2) | 1.0688 (2) | 0.2138 (1) | 0.0380 (4) | |
O2 | −0.2272 (2) | 1.0943 (2) | 0.3432 (1) | 0.0439 (4) | |
O3 | 0.0388 (2) | 1.1917 (2) | 0.3796 (1) | 0.0410 (4) | |
O4 | 0.2026 (2) | 0.7695 (2) | 0.2739 (1) | 0.0341 (4) | |
O1W | 0.0280 (2) | 0.4887 (3) | 0.1804 (1) | 0.0456 (4) | |
N1 | 0.3542 (2) | 0.5628 (2) | 0.4419 (1) | 0.0224 (3) | |
C1 | −0.0209 (2) | 0.8371 (3) | 0.3671 (2) | 0.0269 (4) | |
C2 | 0.1515 (2) | 0.7918 (3) | 0.3717 (2) | 0.0276 (4) | |
C3 | 0.1849 (2) | 0.6160 (3) | 0.4348 (2) | 0.0278 (4) | |
C4 | 0.3757 (2) | 0.3671 (3) | 0.4796 (1) | 0.0242 (4) | |
C5 | 0.4550 (2) | 0.6897 (3) | 0.5117 (1) | 0.0250 (4) | |
H4O | 0.150 (2) | 0.678 (2) | 0.249 (2) | 0.03 (1)* | |
H1W1 | 0.053 (4) | 0.391 (3) | 0.213 (2) | 0.08 (1)* | |
H1W2 | −0.069 (1) | 0.493 (4) | 0.180 (2) | 0.05 (1)* | |
H1N | 0.378 (3) | 0.574 (3) | 0.382 (1) | 0.03 (1)* | |
H1A | −0.0524 | 0.8231 | 0.4348 | 0.032* | |
H1B | −0.0797 | 0.7484 | 0.3226 | 0.032* | |
H2 | 0.2105 | 0.8939 | 0.4067 | 0.033* | |
H3A | 0.1567 | 0.6360 | 0.5029 | 0.033* | |
H3B | 0.1217 | 0.5152 | 0.4039 | 0.033* | |
H4A | 0.3145 | 0.2840 | 0.4329 | 0.029* | |
H4B | 0.3387 | 0.3564 | 0.5458 | 0.029* | |
H5A | 0.4203 | 0.6876 | 0.5789 | 0.030* | |
H5B | 0.4444 | 0.8157 | 0.4860 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0241 (2) | 0.0274 (3) | 0.0229 (3) | 0.0025 (2) | 0.0045 (2) | −0.0002 (2) |
O1 | 0.046 (1) | 0.045 (1) | 0.023 (1) | 0.009 (1) | 0.005 (1) | 0.005 (1) |
O2 | 0.029 (1) | 0.047 (1) | 0.058 (1) | 0.008 (1) | 0.013 (1) | −0.001 (1) |
O3 | 0.044 (1) | 0.037 (1) | 0.041 (1) | −0.010 (1) | 0.002 (1) | −0.006 (1) |
O4 | 0.029 (1) | 0.042 (1) | 0.033 (1) | 0.004 (1) | 0.012 (1) | 0.004 (1) |
O1W | 0.041 (1) | 0.041 (1) | 0.055 (1) | 0.009 (1) | 0.006 (1) | 0.002 (1) |
N1 | 0.022 (1) | 0.026 (1) | 0.020 (1) | 0.003 (1) | 0.002 (1) | 0.002 (1) |
C1 | 0.024 (1) | 0.029 (1) | 0.029 (1) | 0.001 (1) | 0.006 (1) | 0.002 (1) |
C2 | 0.024 (1) | 0.032 (1) | 0.027 (1) | 0.004 (1) | 0.003 (1) | 0.001 (1) |
C3 | 0.022 (1) | 0.030 (1) | 0.031 (1) | 0.003 (1) | 0.003 (1) | 0.002 (1) |
C4 | 0.026 (1) | 0.022 (1) | 0.024 (1) | −0.002 (1) | −0.001 (1) | 0.002 (1) |
C5 | 0.028 (1) | 0.021 (1) | 0.025 (1) | 0.001 (1) | 0.000 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
S1—O1 | 1.454 (1) | O1W—H1W1 | 0.84 (1) |
S1—O2 | 1.454 (2) | O1W—H1W2 | 0.84 (1) |
S1—O3 | 1.445 (2) | N1—H1N | 0.85 (1) |
S1—C1 | 1.780 (2) | C1—H1A | 0.97 |
O4—C2 | 1.422 (2) | C1—H1B | 0.97 |
N1—C4 | 1.500 (2) | C2—H2 | 0.98 |
N1—C5 | 1.503 (2) | C3—H3A | 0.97 |
N1—C3 | 1.508 (2) | C3—H3B | 0.97 |
C1—C2 | 1.524 (2) | C4—H4A | 0.97 |
C2—C3 | 1.524 (3) | C4—H4B | 0.97 |
C4—C5i | 1.514 (3) | C5—H5A | 0.97 |
C5—C4i | 1.514 (3) | C5—H5B | 0.97 |
O4—H4O | 0.85 (1) | | |
| | | |
O3—S1—O1 | 112.2 (1) | S1—C1—H1A | 108.9 |
O3—S1—O2 | 112.0 (1) | C2—C1—H1B | 108.9 |
O1—S1—O2 | 112.6 (1) | S1—C1—H1B | 108.9 |
O3—S1—C1 | 107.5 (1) | H1A—C1—H1B | 107.7 |
O1—S1—C1 | 107.4 (1) | O4—C2—H2 | 108.1 |
O2—S1—C1 | 104.7 (1) | C1—C2—H2 | 108.1 |
C4—N1—C5 | 109.2 (1) | C3—C2—H2 | 108.1 |
C4—N1—C3 | 110.0 (1) | N1—C3—H3A | 109.3 |
C5—N1—C3 | 111.9 (1) | C2—C3—H3A | 109.3 |
C2—C1—S1 | 113.3 (1) | N1—C3—H3B | 109.3 |
O4—C2—C1 | 113.5 (2) | C2—C3—H3B | 109.3 |
O4—C2—C3 | 110.1 (2) | H3A—C3—H3B | 108.0 |
C1—C2—C3 | 108.7 (2) | N1—C4—H4A | 109.4 |
N1—C3—C2 | 111.4 (2) | C5i—C4—H4A | 109.4 |
N1—C4—C5i | 111.1 (2) | N1—C4—H4B | 109.4 |
N1—C5—C4i | 111.7 (2) | C5i—C4—H4B | 109.4 |
C2—O4—H4O | 104 (2) | H4A—C4—H4B | 108.0 |
H1W1—O1W—H1W2 | 103 (3) | N1—C5—H5A | 109.3 |
C4—N1—H1N | 112 (2) | C4i—C5—H5A | 109.3 |
C5—N1—H1N | 109 (2) | N1—C5—H5B | 109.3 |
C3—N1—H1N | 105 (2) | C4i—C5—H5B | 109.3 |
C2—C1—H1A | 108.9 | H5A—C5—H5B | 107.9 |
| | | |
O3—S1—C1—C2 | −49.5 (2) | O4—C2—C3—N1 | 54.8 (2) |
O1—S1—C1—C2 | 71.4 (2) | C1—C2—C3—N1 | 179.7 (2) |
O2—S1—C1—C2 | −168.7 (1) | C5—N1—C4—C5i | −56.4 (2) |
S1—C1—C2—O4 | −71.2 (2) | C3—N1—C4—C5i | −179.5 (2) |
S1—C1—C2—C3 | 166.0 (1) | C4—N1—C5—C4i | 56.7 (2) |
C4—N1—C3—C2 | −165.2 (2) | C3—N1—C5—C4i | 178.7 (2) |
C5—N1—C3—C2 | 73.3 (2) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4O···O1W | 0.85 (1) | 1.89 (1) | 2.732 (3) | 174 (2) |
O1W—H1W2···O2ii | 0.84 (1) | 1.90 (2) | 2.698 (2) | 157 (3) |
O1W—H1W1···O4iii | 0.84 (1) | 2.28 (3) | 2.824 (2) | 123 (3) |
N1—H1N···O1iii | 0.85 (1) | 2.09 (2) | 2.834 (2) | 147 (2) |
Symmetry codes: (ii) −x−1/2, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2. |