organic compounds
Creatininium phosphite
aDepartment of Physics, Nesamony Memorial Christian College, Marthandam, Kaniyakumari, Tamilnadu, India, bDepartment of Physics and Research Centre, Womens Christian College, Nagercoil, Kaniyakumari, Tamilnadu, India, and cDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com
The title salt, C4H8N3O+·H2PO3−, contains a creatininium cation (2-amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium) and a phosphite anion. The crystal packing shows layers of hydrogen-bonded ions lying parallel to the (-114) and (11-4) planes.
Keywords: crystal structure; creatininium phosphite; renal dysfunction.
CCDC reference: 1562051
Structure description
Creatinine as one such material is more valuable for the detection of renal dysfunction than urea (Sharma et al., 2004).
The title compound comprises a protonated creatininium cation and a deprotonated phosphite anion (Fig. 1). The geometric parameters of the title ion-pair agree well with those reported for a similar structure (Thayanithi et al., 2016). The crystal packing (Fig. 2) shows planes of hydrogen-bonded ions parallel to the (14) and (11) planes (Table 1).
Synthesis and crystallization
The title compound was synthesized by dissolving creatinine (1.1312 g, 0.01 mol) in 30 ml of deionized water. Phosphorus acid (0.82 g, 0.01 mol) was then added slowly. The solution was stirred for 4 h, filtered into a beaker and kept dust-free. Colourless crystals were obtained from the mother solution in 93% yield.
Refinement
Crystal data, data collection and structure .
details are presented in Table 2
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Structural data
CCDC reference: 1562051
https://doi.org/10.1107/S2414314617010434/bt4053sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010434/bt4053Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617010434/bt4053Isup3.cml
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C4H8N3O+·H2O3P− | F(000) = 408 |
Mr = 195.12 | Dx = 1.493 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2806 reflections |
a = 8.8083 (11) Å | θ = 2.7–31.3° |
b = 6.6316 (9) Å | µ = 0.30 mm−1 |
c = 15.068 (2) Å | T = 296 K |
β = 99.539 (4)° | Block, colourless |
V = 868.0 (2) Å3 | 0.20 × 0.20 × 0.15 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2806 independent reflections |
Radiation source: fine-focus sealed tube | 1735 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 0 pixels mm-1 | θmax = 31.3°, θmin = 2.7° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→9 |
Tmin = 0.942, Tmax = 0.956 | l = −21→22 |
17033 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.7395P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2806 reflections | Δρmax = 0.41 e Å−3 |
112 parameters | Δρmin = −0.48 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (3) |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9486 (3) | 0.6568 (4) | 0.82130 (17) | 0.0371 (6) | |
C2 | 0.7886 (3) | 0.5893 (4) | 0.78225 (18) | 0.0411 (6) | |
H2A | 0.7124 | 0.6864 | 0.7945 | 0.049* | |
H2B | 0.7781 | 0.5690 | 0.7178 | 0.049* | |
C3 | 0.9043 (3) | 0.3583 (4) | 0.88290 (15) | 0.0288 (5) | |
C4 | 0.6448 (4) | 0.2661 (5) | 0.8068 (2) | 0.0604 (9) | |
H4A | 0.6381 | 0.2209 | 0.7458 | 0.091* | |
H4B | 0.5519 | 0.3359 | 0.8135 | 0.091* | |
H4C | 0.6582 | 0.1519 | 0.8465 | 0.091* | |
N1 | 1.0075 (2) | 0.5102 (3) | 0.88175 (14) | 0.0311 (4) | |
H1 | 1.0973 | 0.5141 | 0.9144 | 0.037* | |
N2 | 0.7741 (2) | 0.4002 (3) | 0.82874 (14) | 0.0369 (5) | |
N3 | 0.9339 (2) | 0.1983 (3) | 0.93186 (15) | 0.0394 (5) | |
H3A | 0.8651 | 0.1060 | 0.9311 | 0.047* | |
H3B | 1.0225 | 0.1842 | 0.9652 | 0.047* | |
O1 | 1.0143 (3) | 0.8075 (3) | 0.80485 (15) | 0.0575 (6) | |
O2 | 1.3127 (2) | 0.4455 (3) | 0.95142 (14) | 0.0501 (6) | |
O3 | 1.2272 (2) | 0.1521 (3) | 1.03801 (13) | 0.0435 (5) | |
O4 | 1.4909 (2) | 0.2863 (3) | 1.08076 (14) | 0.0506 (6) | |
H4 | 1.5505 | 0.3698 | 1.0658 | 0.076* | |
P1 | 1.35438 (7) | 0.25366 (10) | 1.00218 (5) | 0.0336 (2) | |
H1A | 1.3903 | 0.1593 | 0.9601 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0422 (14) | 0.0362 (14) | 0.0346 (13) | 0.0032 (11) | 0.0109 (11) | 0.0059 (11) |
C2 | 0.0395 (14) | 0.0473 (15) | 0.0351 (13) | 0.0085 (12) | 0.0024 (11) | 0.0080 (12) |
C3 | 0.0269 (11) | 0.0309 (12) | 0.0283 (11) | −0.0017 (9) | 0.0037 (9) | −0.0001 (9) |
C4 | 0.0389 (16) | 0.074 (2) | 0.061 (2) | −0.0176 (16) | −0.0118 (14) | 0.0016 (17) |
N1 | 0.0279 (10) | 0.0288 (10) | 0.0354 (10) | −0.0039 (8) | 0.0018 (8) | 0.0028 (8) |
N2 | 0.0279 (10) | 0.0444 (12) | 0.0366 (11) | −0.0025 (9) | −0.0001 (8) | 0.0037 (9) |
N3 | 0.0307 (11) | 0.0323 (11) | 0.0511 (13) | −0.0109 (9) | −0.0055 (10) | 0.0085 (10) |
O1 | 0.0677 (15) | 0.0442 (12) | 0.0624 (14) | −0.0077 (10) | 0.0158 (11) | 0.0210 (10) |
O2 | 0.0263 (9) | 0.0522 (12) | 0.0668 (14) | −0.0108 (8) | −0.0071 (9) | 0.0278 (10) |
O3 | 0.0318 (10) | 0.0419 (11) | 0.0554 (11) | −0.0127 (8) | 0.0033 (8) | 0.0104 (9) |
O4 | 0.0342 (10) | 0.0585 (14) | 0.0536 (12) | −0.0164 (9) | −0.0090 (9) | 0.0230 (10) |
P1 | 0.0249 (3) | 0.0355 (3) | 0.0398 (4) | −0.0038 (3) | 0.0034 (2) | 0.0050 (3) |
C1—O1 | 1.201 (3) | C4—H4B | 0.9600 |
C1—N1 | 1.374 (3) | C4—H4C | 0.9600 |
C1—C2 | 1.502 (4) | N1—H1 | 0.8600 |
C2—N2 | 1.452 (4) | N3—H3A | 0.8600 |
C2—H2A | 0.9700 | N3—H3B | 0.8600 |
C2—H2B | 0.9700 | O2—P1 | 1.4983 (19) |
C3—N3 | 1.294 (3) | O3—P1 | 1.4833 (18) |
C3—N2 | 1.322 (3) | O4—P1 | 1.5566 (19) |
C3—N1 | 1.359 (3) | O4—H4 | 0.8200 |
C4—N2 | 1.440 (4) | P1—H1A | 0.9800 |
C4—H4A | 0.9600 | ||
O1—C1—N1 | 125.7 (3) | H4B—C4—H4C | 109.5 |
O1—C1—C2 | 128.3 (2) | C3—N1—C1 | 110.7 (2) |
N1—C1—C2 | 106.0 (2) | C3—N1—H1 | 124.7 |
N2—C2—C1 | 102.7 (2) | C1—N1—H1 | 124.7 |
N2—C2—H2A | 111.2 | C3—N2—C4 | 125.7 (2) |
C1—C2—H2A | 111.2 | C3—N2—C2 | 110.0 (2) |
N2—C2—H2B | 111.2 | C4—N2—C2 | 123.5 (2) |
C1—C2—H2B | 111.2 | C3—N3—H3A | 120.0 |
H2A—C2—H2B | 109.1 | C3—N3—H3B | 120.0 |
N3—C3—N2 | 126.6 (2) | H3A—N3—H3B | 120.0 |
N3—C3—N1 | 122.9 (2) | P1—O4—H4 | 109.5 |
N2—C3—N1 | 110.5 (2) | O3—P1—O2 | 115.80 (11) |
N2—C4—H4A | 109.5 | O3—P1—O4 | 108.73 (11) |
N2—C4—H4B | 109.5 | O2—P1—O4 | 111.31 (11) |
H4A—C4—H4B | 109.5 | O3—P1—H1A | 106.8 |
N2—C4—H4C | 109.5 | O2—P1—H1A | 106.8 |
H4A—C4—H4C | 109.5 | O4—P1—H1A | 106.8 |
O1—C1—C2—N2 | −179.2 (3) | N3—C3—N2—C4 | −6.6 (4) |
N1—C1—C2—N2 | 0.4 (3) | N1—C3—N2—C4 | 173.9 (3) |
N3—C3—N1—C1 | 177.4 (2) | N3—C3—N2—C2 | −177.2 (2) |
N2—C3—N1—C1 | −3.1 (3) | N1—C3—N2—C2 | 3.4 (3) |
O1—C1—N1—C3 | −178.9 (3) | C1—C2—N2—C3 | −2.3 (3) |
C2—C1—N1—C3 | 1.5 (3) | C1—C2—N2—C4 | −173.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O1i | 0.97 | 2.58 | 2.997 (4) | 106 |
C4—H4C···N3 | 0.96 | 2.57 | 2.941 (4) | 103 |
C4—H4A···O4ii | 0.96 | 2.61 | 3.470 (3) | 150 |
N1—H1···O2 | 0.86 | 1.94 | 2.754 (2) | 157 |
N3—H3A···O3iii | 0.86 | 1.98 | 2.800 (2) | 158 |
N3—H3B···O3 | 0.86 | 1.96 | 2.821 (2) | 178 |
O4—H4···O2iv | 0.82 | 1.77 | 2.585 (2) | 170 |
Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) x−1, −y+1/2, z−1/2; (iii) −x+2, −y, −z+2; (iv) −x+3, −y+1, −z+2. |
Acknowledgements
The authors acknowledge the SAIF, IIT Madras, Chennai.
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