Bis(2-amino-5-chloro­pyridinium) dihydrogen­diphosphate

The title compound, 2C₅H₆ClN₂⁺·H₂P₂O₇^2-, contains infinite (H₂P₂O₇^2-)_n ribbons extending along the c direction. The bridging O atom of the diphosphate anion is located on a twofold axis. The organic cations are anchored between planes parallel to ac, linking the ribbons into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.112
• Data-to-parameter ratio = 25.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(2-amino-5-chloropyridinium) dihydrogenodiphosphate

Crystal data

2C5H6ClN2^+·H2O7P2^2^−	F(000) = 888
Mr = 435.10	Dx = 1.745 Mg m^−3
Monoclinic, C2/c	Ag Kα radiation, λ = 0.5608 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 16.872 (8) Å	θ = 9–11°
b = 11.144 (3) Å	µ = 0.33 mm^−1
c = 11.266 (5) Å	T = 293 K
β = 128.55 (3)°	Prism, colorless
V = 1656.6 (14) Å^3	0.23 × 0.17 × 0.15 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.019
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.0°
Graphite monochromator	h = −16→25
ω/2θ scans	k = 0→16
3057 measured reflections	l = −16→16
2948 independent reflections	2 standard reflections every 400 reflections
2589 reflections with I > 2σ(I)	intensity decay: 0.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 1.4425P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
2948 reflections	Δρmax = 0.52 e Å^−3
116 parameters	Δρmin = −0.64 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0150 (15)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.10360 (3)	0.69189 (3)	0.80774 (4)	0.02292 (10)
Cl1	0.13829 (6)	0.06962 (5)	0.62168 (7)	0.06080 (18)
O1	0.16158 (8)	0.65349 (10)	0.96990 (11)	0.0288 (2)
O2	0.15747 (9)	0.79654 (12)	0.79150 (13)	0.0376 (3)
H2	0.2107	0.8129	0.8751	0.056*
O3	0.07753 (9)	0.59227 (10)	0.69954 (12)	0.0313 (2)
O4	0.0000	0.75589 (13)	0.7500	0.0286 (3)
N1	0.11862 (10)	0.36380 (11)	0.79413 (14)	0.0284 (2)
H1	0.1138	0.4393	0.7750	0.034*
N2	0.11939 (12)	0.40957 (13)	0.99393 (16)	0.0349 (3)
H2A	0.1158	0.4844	0.9725	0.042*
H2B	0.1214	0.3880	1.0691	0.042*
C1	0.12187 (11)	0.32788 (13)	0.91168 (16)	0.0271 (3)
C2	0.12762 (12)	0.20242 (14)	0.94005 (18)	0.0322 (3)
H2C	0.1285	0.1743	1.0185	0.039*
C3	0.13188 (13)	0.12390 (15)	0.8516 (2)	0.0364 (3)
H3	0.1358	0.0419	0.8698	0.044*
C4	0.13037 (13)	0.16686 (15)	0.73228 (19)	0.0343 (3)
C5	0.12257 (12)	0.28679 (14)	0.70490 (18)	0.0313 (3)
H5	0.1199	0.3159	0.6251	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.02296 (16)	0.02414 (17)	0.02482 (17)	−0.00190 (11)	0.01644 (13)	0.00084 (11)
Cl1	0.0984 (5)	0.0382 (2)	0.0715 (4)	−0.0024 (3)	0.0656 (4)	−0.0126 (2)
O1	0.0280 (5)	0.0329 (5)	0.0256 (4)	−0.0054 (4)	0.0167 (4)	0.0022 (4)
O2	0.0299 (5)	0.0441 (6)	0.0334 (5)	−0.0101 (5)	0.0171 (5)	0.0094 (5)
O3	0.0373 (5)	0.0311 (5)	0.0320 (5)	0.0021 (4)	0.0247 (5)	−0.0020 (4)
O4	0.0262 (6)	0.0225 (6)	0.0395 (8)	0.000	0.0216 (6)	0.000
N1	0.0351 (6)	0.0259 (5)	0.0318 (6)	0.0045 (4)	0.0245 (5)	0.0055 (4)
N2	0.0490 (8)	0.0317 (6)	0.0353 (6)	0.0051 (5)	0.0318 (6)	0.0051 (5)
C1	0.0266 (6)	0.0297 (6)	0.0279 (6)	0.0033 (5)	0.0185 (5)	0.0049 (5)
C2	0.0362 (7)	0.0299 (7)	0.0358 (7)	0.0031 (5)	0.0250 (6)	0.0081 (5)
C3	0.0413 (8)	0.0273 (6)	0.0453 (8)	0.0018 (6)	0.0293 (7)	0.0047 (6)
C4	0.0406 (8)	0.0298 (7)	0.0397 (8)	0.0003 (6)	0.0285 (7)	−0.0019 (6)
C5	0.0377 (7)	0.0314 (7)	0.0348 (7)	0.0020 (5)	0.0275 (6)	0.0017 (5)

Geometric parameters (Å, º)

P1—O3	1.4978 (12)	N2—C1	1.318 (2)
P1—O1	1.5001 (13)	N2—H2A	0.8600
P1—O2	1.5577 (12)	N2—H2B	0.8600
P1—O4	1.6031 (11)	C1—C2	1.424 (2)
Cl1—C4	1.7183 (17)	C2—C3	1.361 (2)
O2—H2	0.8200	C2—H2C	0.9300
O4—P1^i	1.6031 (11)	C3—C4	1.413 (2)
N1—C1	1.3515 (18)	C3—H3	0.9300
N1—C5	1.3546 (19)	C4—C5	1.359 (2)
N1—H1	0.8600	C5—H5	0.9300
O3—P1—O1	114.68 (7)	N2—C1—C2	123.22 (13)
O3—P1—O2	110.87 (8)	N1—C1—C2	117.80 (13)
O1—P1—O2	111.79 (7)	C3—C2—C1	119.62 (14)
O3—P1—O4	107.85 (7)	C3—C2—H2C	120.2
O1—P1—O4	109.85 (6)	C1—C2—H2C	120.2
O2—P1—O4	100.82 (8)	C2—C3—C4	120.06 (15)
P1—O2—H2	109.5	C2—C3—H3	120.0
P1^i—O4—P1	127.17 (10)	C4—C3—H3	120.0
C1—N1—C5	123.28 (13)	C5—C4—C3	119.41 (15)
C1—N1—H1	118.4	C5—C4—Cl1	119.72 (13)
C5—N1—H1	118.4	C3—C4—Cl1	120.87 (13)
C1—N2—H2A	120.0	N1—C5—C4	119.80 (14)
C1—N2—H2B	120.0	N1—C5—H5	120.1
H2A—N2—H2B	120.0	C4—C5—H5	120.1
N2—C1—N1	118.98 (13)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^ii	0.82	1.77	2.574 (2)	165
N1—H1···O3	0.86	1.83	2.6792 (18)	168
N2—H2A···O1	0.86	2.04	2.8651 (19)	160
N2—H2B···O3^iii	0.86	2.03	2.811 (2)	151

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