Creatininium phosphite

Sindhusha, S.; Padma, C.M.; Gunasekaran, B.

doi:10.1107/S2414314617010434

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x171043

https://doi.org/10.1107/S2414314617010434

Open

access

Creatininium phosphite

S. Sindhusha,^a C. M. Padma ^b and B. Gunasekaran ^c ^*

^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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 22 June 2017; accepted 13 July 2017; online 18 July 2017)

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 ( $[\overline{1}]$ 14) and (11 $[\overline{4}]$ ) planes (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1ⁱ	0.97	2.58	2.997 (4)	106
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⋯O2^iv	0.82	1.77	2.585 (2)	170
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+2; (iv) -x+3, -y+1, -z+2.

Figure 1
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for the non-H atoms.

Figure 2
The packing of the title compound, viewed down the b axis. Hydrogen bonds are shown as dashed lines.

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 refinement details are presented in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₄H₈N₃O⁺·H₂O₃P⁻
M_r	195.12
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.8083 (11), 6.6316 (9), 15.068 (2)
β (°)	99.539 (4)
V (Å³)	868.0 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.30
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.942, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	17033, 2806, 1735
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.732

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.152, 1.10
No. of reflections	2806
No. of parameters	112
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.48
Computer programs: APEX2 and SAINT (Bruker, 2008 ), SHELXS97and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1562051

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617010434/bt4053sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: 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).

2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-3-ium phosphite top

Crystal data top

C₄H₈N₃O⁺·H₂O₃P⁻	F(000) = 408
M_r = 195.12	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	1735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Detector resolution: 0 pixels mm^-1	θ_max = 31.3°, θ_min = 2.7°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→9
T_min = 0.942, T_max = 0.956	l = −21→22
17033 measured reflections

Refinement top

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(F_o²) + (0.0518P)² + 0.7395P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2806 reflections	Δρ_max = 0.41 e Å⁻³
112 parameters	Δρ_min = −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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sharma, A. C., Jana, T., Kesavamoorthy, R., Shi, L., Virji, M. A., Finegold, D. N. & Asher, S. A. (2004). J. Am. Chem. Soc. 126, 2971–2977. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thayanithi, V., Kumar, P. P. & Gunasekaran, B. (2016). IUCrData, 1, x160989. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 7| July 2017| x171043

https://doi.org/10.1107/S2414314617010434

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text
		Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Creatininium phosphite

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds