dl-Methio­ninium dihydrogenphosphate

Bahadur, S.A.; Athimoolam, S.

doi:10.1107/S1600536807012524

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DL-Methioninium dihydrogenphosphate

S. A. Bahadur and S. Athimoolam

The asymmetric unit of the title compound, C₅H₁₂NO₂S⁺·H₂PO₄⁻, contains two crystallographically independent methioninium residues and two dihydrogenphosphate anions. Pairs of cations and anions are linked by strong O—H

O hydrogen bonds. Head-to-tail chains running along the c axis of the unit cell are observed for both cationic residues. Alternate hydrophobic and hydrophilic layers are observed parallel to the (010) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012524/rk2003sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807012524/rk2003Isup2.hkl Contains datablock I

CCDC reference: 643077

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.044
wR factor = 0.120
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.67 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.90 Deg.
              C13B -C12  -C13A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.30 Deg.
              H12A -C12  -H12B    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      35.00 Deg.
              C14A -S1   -C14B    1.555   1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC (Bruker, 2000); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC.

DL-Methioninium dihydrogenphosphate top

Crystal data top

C₅H₁₂NO₂S⁺·H₂O₄P⁻	F(000) = 1040
M_r = 247.21	D_x = 1.537 Mg m⁻³ D_m = 1.53 (1) Mg m⁻³ D_m measured by flotation using a mixture of xylene and CCl₄
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 23.935 (4) Å	θ = 11.3–14.2°
b = 9.992 (2) Å	µ = 0.46 mm⁻¹
c = 9.026 (3) Å	T = 293 K
β = 98.25 (2)°	Plate, colourless
V = 2136.3 (9) Å³	0.25 × 0.17 × 0.15 mm
Z = 8

Data collection top

Enraf–Nonius MACH3 diffractometer	3112 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	R_int = 0.013
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω/2θ scans	h = −28→28
Absorption correction: ψ scan (North et al., 1968)	k = −1→11
T_min = 0.872, T_max = 0.953	l = 0→10
4507 measured reflections	3 standard reflections every 60 min
3742 independent reflections	intensity decay: none

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.0282P)² + 4.6019P] where P = (F_o² + 2F_c²)/3
3742 reflections	(Δ/σ)_max = 0.001
279 parameters	Δρ_max = 0.48 e Å⁻³
6 restraints	Δρ_min = −0.52 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C11	0.08512 (14)	0.3232 (3)	0.5520 (4)	0.0301 (8)
O1A	0.06527 (13)	0.3678 (2)	0.6607 (3)	0.0432 (7)
O1B	0.10413 (11)	0.3932 (2)	0.4511 (3)	0.0373 (6)
H1B	0.1009	0.4730	0.4695	0.056*
C12	0.09000 (14)	0.1725 (4)	0.5340 (4)	0.0379 (9)
H12A	0.0791	0.1467	0.4291	0.045*	0.71
H12B	0.0641	0.1652	0.4400	0.045*	0.29
N1	0.05336 (13)	0.1063 (3)	0.6298 (3)	0.0349 (7)
H1A	0.0559	0.0180	0.6202	0.052*
H1C	0.0178	0.1319	0.6023	0.052*
H1D	0.0643	0.1291	0.7249	0.052*
C13A	0.15011 (17)	0.1233 (6)	0.5921 (6)	0.0401 (13)	0.71
H13A	0.1643	0.1717	0.6830	0.048*	0.71
H13B	0.1486	0.0291	0.6173	0.048*	0.71
C14A	0.1908 (2)	0.1420 (6)	0.4790 (7)	0.0494 (15)	0.71
H14A	0.1953	0.2368	0.4608	0.059*	0.71
H14B	0.1752	0.1005	0.3850	0.059*	0.71
C13B	0.1415 (3)	0.1161 (12)	0.4760 (11)	0.035 (3)	0.29
H13C	0.1484	0.1634	0.3866	0.042*	0.29
H13D	0.1362	0.0219	0.4520	0.042*	0.29
C14B	0.1905 (4)	0.1352 (17)	0.6012 (13)	0.059 (5)	0.29
H14C	0.1828	0.0879	0.6899	0.071*	0.29
H14D	0.1946	0.2296	0.6257	0.071*	0.29
S1	0.25811 (5)	0.07041 (13)	0.54340 (16)	0.0616 (4)
C15	0.2435 (2)	−0.1045 (5)	0.5374 (7)	0.0668 (14)
H15A	0.2171	−0.1246	0.4499	0.100*
H15B	0.2278	−0.1300	0.6253	0.100*
H15C	0.2779	−0.1532	0.5338	0.100*
C21	0.41123 (14)	0.1752 (3)	0.4842 (4)	0.0262 (7)
O2A	0.43427 (12)	0.1351 (2)	0.6070 (3)	0.0384 (6)
O2B	0.39283 (11)	0.1011 (2)	0.3708 (3)	0.0334 (6)
H2B	0.3947	0.0222	0.3959	0.050*
C22	0.40142 (14)	0.3242 (3)	0.4590 (4)	0.0275 (7)
H22	0.4096	0.3480	0.3590	0.033*
N2	0.44111 (12)	0.3963 (3)	0.5731 (3)	0.0302 (6)
H2A	0.4362	0.4841	0.5608	0.045*
H2C	0.4764	0.3748	0.5626	0.045*
H2D	0.4345	0.3731	0.6641	0.045*
C23	0.33944 (15)	0.3561 (4)	0.4694 (4)	0.0374 (8)
H23A	0.3157	0.2990	0.3998	0.045*
H23B	0.3320	0.3344	0.5694	0.045*
C24	0.32278 (16)	0.4997 (4)	0.4363 (5)	0.0441 (10)
H24A	0.3309	0.5229	0.3373	0.053*
H24B	0.3453	0.5574	0.5079	0.053*
S2	0.24886 (5)	0.52975 (13)	0.44510 (15)	0.0587 (3)
C25	0.2493 (2)	0.5354 (7)	0.6434 (6)	0.0805 (17)
H25A	0.2772	0.5986	0.6868	0.121*
H25B	0.2583	0.4484	0.6852	0.121*
H25C	0.2128	0.5623	0.6646	0.121*
P1	0.07663 (4)	0.71275 (9)	0.60099 (10)	0.0281 (2)
O11	0.03261 (11)	0.6181 (3)	0.6591 (3)	0.0407 (6)
H11	0.0447	0.5412	0.6633	0.061*
O12	0.04872 (11)	0.8413 (2)	0.5547 (3)	0.0394 (6)
O13	0.12700 (11)	0.7309 (3)	0.7294 (3)	0.0443 (7)
H13	0.1157	0.7665	0.8015	0.066*
O14	0.10187 (11)	0.6404 (2)	0.4759 (3)	0.0348 (6)
P2	0.43098 (4)	0.79179 (8)	0.55904 (10)	0.0268 (2)
O21	0.47562 (10)	0.8904 (2)	0.6428 (3)	0.0375 (6)
H21	0.4636	0.9672	0.6333	0.056*
O22	0.45957 (10)	0.6623 (2)	0.5378 (3)	0.0362 (6)
O23	0.38277 (10)	0.7758 (3)	0.6575 (3)	0.0389 (6)
H23	0.3951	0.7372	0.7356	0.058*
O24	0.40343 (11)	0.8569 (2)	0.4143 (3)	0.0337 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0302 (17)	0.0268 (18)	0.0325 (18)	0.0031 (14)	0.0016 (15)	−0.0011 (15)
O1A	0.0742 (19)	0.0234 (13)	0.0357 (14)	0.0044 (13)	0.0205 (13)	0.0016 (11)
O1B	0.0505 (15)	0.0250 (13)	0.0388 (14)	−0.0019 (12)	0.0150 (12)	−0.0023 (11)
C12	0.044 (2)	0.0250 (19)	0.049 (2)	−0.0012 (16)	0.0200 (18)	−0.0040 (16)
N1	0.0449 (17)	0.0219 (15)	0.0384 (16)	0.0024 (13)	0.0074 (14)	−0.0001 (13)
C13A	0.047 (3)	0.034 (3)	0.041 (4)	0.011 (3)	0.012 (3)	0.003 (3)
C14A	0.049 (4)	0.045 (4)	0.057 (4)	0.004 (3)	0.015 (3)	0.013 (3)
C13B	0.047 (8)	0.038 (7)	0.021 (6)	0.007 (6)	0.011 (5)	0.002 (5)
C14B	0.086 (13)	0.050 (10)	0.038 (9)	0.037 (10)	−0.006 (9)	−0.009 (7)
S1	0.0422 (6)	0.0523 (7)	0.0883 (9)	0.0009 (5)	0.0031 (6)	0.0076 (6)
C15	0.059 (3)	0.046 (3)	0.096 (4)	0.011 (2)	0.012 (3)	0.002 (3)
C21	0.0320 (17)	0.0209 (16)	0.0271 (17)	0.0019 (14)	0.0087 (14)	−0.0017 (14)
O2A	0.0620 (17)	0.0219 (12)	0.0294 (13)	0.0055 (12)	0.0004 (12)	0.0002 (10)
O2B	0.0469 (14)	0.0205 (12)	0.0320 (13)	0.0007 (11)	0.0031 (11)	0.0011 (10)
C22	0.0363 (18)	0.0217 (17)	0.0246 (16)	0.0000 (14)	0.0045 (14)	0.0012 (13)
N2	0.0322 (15)	0.0203 (14)	0.0381 (16)	0.0020 (12)	0.0054 (12)	−0.0003 (12)
C23	0.0351 (19)	0.0285 (19)	0.048 (2)	0.0016 (16)	0.0036 (16)	−0.0007 (17)
C24	0.039 (2)	0.034 (2)	0.059 (3)	0.0050 (17)	0.0032 (18)	0.0026 (19)
S2	0.0383 (6)	0.0631 (8)	0.0723 (8)	0.0138 (5)	0.0001 (5)	−0.0032 (6)
C25	0.065 (3)	0.102 (5)	0.075 (4)	0.027 (3)	0.014 (3)	−0.001 (3)
P1	0.0328 (5)	0.0217 (4)	0.0301 (5)	0.0038 (4)	0.0057 (4)	−0.0007 (4)
O11	0.0465 (15)	0.0279 (13)	0.0520 (16)	0.0016 (12)	0.0221 (13)	0.0004 (12)
O12	0.0488 (15)	0.0216 (13)	0.0468 (15)	0.0054 (11)	0.0031 (12)	−0.0004 (11)
O13	0.0405 (15)	0.0543 (18)	0.0375 (14)	0.0091 (13)	0.0034 (12)	−0.0098 (13)
O14	0.0497 (15)	0.0268 (13)	0.0301 (12)	0.0043 (11)	0.0136 (11)	0.0021 (10)
P2	0.0321 (5)	0.0190 (4)	0.0297 (4)	0.0030 (3)	0.0057 (4)	0.0004 (3)
O21	0.0396 (14)	0.0249 (13)	0.0454 (15)	0.0021 (11)	−0.0033 (11)	−0.0014 (12)
O22	0.0400 (14)	0.0214 (12)	0.0488 (15)	0.0048 (11)	0.0118 (12)	0.0010 (11)
O23	0.0373 (14)	0.0466 (16)	0.0339 (13)	0.0084 (12)	0.0094 (11)	0.0078 (12)
O24	0.0526 (15)	0.0213 (12)	0.0264 (12)	0.0020 (11)	0.0026 (11)	−0.0008 (10)

Geometric parameters (Å, º) top

C11—O1A	1.233 (4)	C21—C22	1.519 (4)
C11—O1B	1.283 (4)	O2B—H2B	0.8200
C11—C12	1.520 (5)	C22—N2	1.483 (4)
O1B—H1B	0.8200	C22—C23	1.533 (5)
C12—N1	1.474 (4)	C22—H22	0.9800
C12—C13B	1.516 (3)	N2—H2A	0.8900
C12—C13A	1.540 (3)	N2—H2C	0.8900
C12—H12A	0.9800	N2—H2D	0.8900
C12—H12B	0.9800	C23—C24	1.507 (5)
N1—H1A	0.8900	C23—H23A	0.9700
N1—H1C	0.8900	C23—H23B	0.9700
N1—H1D	0.8900	C24—S2	1.807 (4)
C13A—C14A	1.520 (3)	C24—H24A	0.9700
C13A—H13A	0.9700	C24—H24B	0.9700
C13A—H13B	0.9700	S2—C25	1.789 (6)
C14A—S1	1.782 (5)	C25—H25A	0.9600
C14A—H14A	0.9700	C25—H25B	0.9600
C14A—H14B	0.9700	C25—H25C	0.9600
C13B—C14B	1.520 (3)	P1—O11	1.562 (3)
C13B—H13C	0.9700	P1—O12	1.480 (3)
C13B—H13D	0.9700	P1—O13	1.559 (3)
C14B—S1	1.885 (9)	P1—O14	1.536 (2)
C14B—H14C	0.9700	O11—H11	0.8200
C14B—H14D	0.9700	O13—H13	0.8200
S1—C15	1.782 (5)	P2—O21	1.566 (3)
C15—H15A	0.9600	P2—O22	1.489 (2)
C15—H15B	0.9600	P2—O23	1.562 (3)
C15—H15C	0.9600	P2—O24	1.522 (2)
C21—O2A	1.232 (4)	O21—H21	0.8200
C21—O2B	1.288 (4)	O23—H23	0.8200

O1A—C11—O1B	125.8 (3)	S1—C15—H15C	109.5
O1A—C11—C12	119.1 (3)	H15A—C15—H15C	109.5
O1B—C11—C12	115.1 (3)	H15B—C15—H15C	109.5
C11—O1B—H1B	109.5	O2A—C21—O2B	125.9 (3)
N1—C12—C13B	128.1 (6)	O2A—C21—C22	119.5 (3)
N1—C12—C11	108.7 (3)	O2B—C21—C22	114.6 (3)
C13B—C12—C11	119.0 (6)	C21—O2B—H2B	109.5
N1—C12—C13A	105.2 (3)	N2—C22—C21	107.6 (3)
C13B—C12—C13A	39.9 (4)	N2—C22—C23	112.7 (3)
C11—C12—C13A	111.2 (4)	C21—C22—C23	109.0 (3)
N1—C12—H12A	110.5	N2—C22—H22	109.2
C13B—C12—H12A	71.6	C21—C22—H22	109.2
C11—C12—H12A	110.5	C23—C22—H22	109.2
C13A—C12—H12A	110.5	C22—N2—H2A	109.5
N1—C12—H12B	96.8	C22—N2—H2C	109.5
C13B—C12—H12B	96.8	H2A—N2—H2C	109.5
C11—C12—H12B	96.8	C22—N2—H2D	109.5
C13A—C12—H12B	135.7	H2A—N2—H2D	109.5
H12A—C12—H12B	25.3	H2C—N2—H2D	109.5
C12—N1—H1A	109.5	C24—C23—C22	114.7 (3)
C12—N1—H1C	109.5	C24—C23—H23A	108.6
H1A—N1—H1C	109.5	C22—C23—H23A	108.6
C12—N1—H1D	109.5	C24—C23—H23B	108.6
H1A—N1—H1D	109.5	C22—C23—H23B	108.6
H1C—N1—H1D	109.5	H23A—C23—H23B	107.6
C14A—C13A—C12	112.9 (4)	C23—C24—S2	112.5 (3)
C14A—C13A—H13A	109.0	C23—C24—H24A	109.1
C12—C13A—H13A	109.0	S2—C24—H24A	109.1
C14A—C13A—H13B	109.0	C23—C24—H24B	109.1
C12—C13A—H13B	109.0	S2—C24—H24B	109.1
H13A—C13A—H13B	107.8	H24A—C24—H24B	107.8
C13A—C14A—S1	111.6 (3)	C25—S2—C24	100.6 (2)
C13A—C14A—H14A	109.3	S2—C25—H25A	109.5
S1—C14A—H14A	109.3	S2—C25—H25B	109.5
C13A—C14A—H14B	109.3	H25A—C25—H25B	109.5
S1—C14A—H14B	109.3	S2—C25—H25C	109.5
H14A—C14A—H14B	108.0	H25A—C25—H25C	109.5
C12—C13B—C14B	106.0 (6)	H25B—C25—H25C	109.5
C12—C13B—H13C	110.5	O12—P1—O14	114.24 (15)
C14B—C13B—H13C	110.5	O12—P1—O13	112.25 (16)
C12—C13B—H13D	110.5	O14—P1—O13	104.94 (15)
C14B—C13B—H13D	110.5	O12—P1—O11	108.74 (15)
H13C—C13B—H13D	108.7	O14—P1—O11	108.51 (14)
C13B—C14B—S1	110.7 (6)	O13—P1—O11	107.91 (16)
C13B—C14B—H14C	109.5	P1—O11—H11	109.5
S1—C14B—H14C	109.5	P1—O13—H13	109.5
C13B—C14B—H14D	109.5	O22—P2—O24	114.31 (14)
S1—C14B—H14D	109.5	O22—P2—O23	112.00 (15)
H14C—C14B—H14D	108.1	O24—P2—O23	105.50 (14)
C15—S1—C14A	102.7 (3)	O22—P2—O21	108.34 (14)
C15—S1—C14B	100.0 (6)	O24—P2—O21	109.09 (14)
C14A—S1—C14B	35.0 (4)	O23—P2—O21	107.35 (15)
S1—C15—H15A	109.5	P2—O21—H21	109.5
S1—C15—H15B	109.5	P2—O23—H23	109.5
H15A—C15—H15B	109.5

O1A—C11—C12—N1	17.2 (5)	C12—C13B—C14B—S1	−179.5 (8)
O1B—C11—C12—N1	−164.6 (3)	C13A—C14A—S1—C15	69.2 (5)
O1A—C11—C12—C13B	−141.6 (5)	C13A—C14A—S1—C14B	−20.1 (10)
O1B—C11—C12—C13B	36.6 (6)	C13B—C14B—S1—C15	−68.7 (12)
O1A—C11—C12—C13A	−98.2 (4)	C13B—C14B—S1—C14A	29.2 (7)
O1B—C11—C12—C13A	80.0 (4)	O2A—C21—C22—N2	20.9 (4)
N1—C12—C13A—C14A	160.8 (5)	O2B—C21—C22—N2	−160.4 (3)
C13B—C12—C13A—C14A	28.5 (8)	O2A—C21—C22—C23	−101.5 (4)
C11—C12—C13A—C14A	−81.6 (5)	O2B—C21—C22—C23	77.2 (4)
C12—C13A—C14A—S1	−174.7 (4)	N2—C22—C23—C24	64.5 (4)
N1—C12—C13B—C14B	−83.3 (11)	C21—C22—C23—C24	−176.1 (3)
C11—C12—C13B—C14B	71.0 (11)	C22—C23—C24—S2	178.3 (3)
C13A—C12—C13B—C14B	−18.1 (9)	C23—C24—S2—C25	77.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1B—H1B···O14	0.82	1.67	2.481 (3)	168
N1—H1C···O12ⁱ	0.89	1.99	2.802 (4)	151
N1—H1D···O1Bⁱⁱ	0.89	2.14	2.979 (4)	158
N1—H1A···O12ⁱⁱⁱ	0.89	1.86	2.732 (4)	165
O2B—H2B···O24ⁱⁱⁱ	0.82	1.67	2.479 (3)	169
N2—H2A···O22	0.89	1.89	2.721 (4)	155
N2—H2D···O2Bⁱⁱ	0.89	2.25	3.074 (4)	153
N2—H2C···O22^iv	0.89	1.92	2.771 (4)	158
O11—H11···O1A	0.82	1.80	2.620 (3)	175
O13—H13···O14^v	0.82	1.90	2.711 (3)	171
O21—H21···O2A^vi	0.82	1.82	2.641 (3)	178
O23—H23···O24^v	0.82	1.85	2.655 (3)	165

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) x, −y+3/2, z+1/2; (vi) x, y+1, z.

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