2-(2-Pyridylamino)pyridinium chloride phospho­rous acid: one-dimensional hydrogen-bonded and π–π stacked supra­molecular chains

In the crystal structure of the title compound, C₁₀H₁₀N₃⁺·Cl⁻·[P(O)(OH)₂H], the chloride ion and phospho­rous acid form a one-dimensional hydrogen-bonded chain, while the 2-(2-pyridylamino)pyridinium cations form a second chain through π–π stacking. The two parallel chains are connected via a PO...H—N hydrogen bond and a weak pyridinium-to-chloride inter­action.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](P-O) = 0.001 Å
• Disorder in main residue
• R factor = 0.039
• wR factor = 0.110
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT213_ALERT_2_B Atom N3'     has ADP max/min Ratio .............       4.20 prolat
PLAT301_ALERT_3_B Main Residue  Disorder .........................      42.00 Perc.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom C13'    has ADP max/min Ratio .............       3.10 prolat
PLAT213_ALERT_2_C Atom C22'    has ADP max/min Ratio .............       3.50 oblate
PLAT213_ALERT_2_C Atom C24'    has ADP max/min Ratio .............       3.80 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.79 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff et al., 1996); software used to prepare material for publication: SHELXL97.

2-(2-Pyridylamino)pyridinium chloride phosphorous acid

Crystal data

C10H10N3^+·Cl^−·H3O3P	Z = 2
Mr = 289.65	F(000) = 300
Triclinic, P1	Dx = 1.513 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.504 (1) Å	Cell parameters from 6685 reflections
b = 8.840 (1) Å	θ = 2.0–30.5°
c = 10.710 (1) Å	µ = 0.43 mm^−1
α = 76.288 (3)°	T = 173 K
β = 74.840 (3)°	Prism, colourless
γ = 70.054 (3)°	0.50 × 0.24 × 0.19 mm
V = 635.9 (1) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 30.0°, θmin = 2.0°
φ and ω scans	h = −10→10
7690 measured reflections	k = −12→12
3650 independent reflections	l = −12→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0633P)^2 + 0.1848P] where P = (Fo^2 + 2Fc^2)/3
3650 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.50 e Å^−3
33 restraints	Δρmin = −0.56 e Å^−3

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	Occ. (<1)
O1	0.62953 (16)	0.77754 (16)	0.76291 (11)	0.0410 (3)
O2	0.90690 (15)	0.69093 (15)	0.57109 (11)	0.0391 (3)
O3	0.58288 (17)	0.74265 (17)	0.54393 (11)	0.0408 (3)
P	0.69705 (5)	0.79522 (4)	0.61958 (3)	0.02832 (11)
Cl	0.83419 (5)	1.18554 (5)	0.33993 (4)	0.03750 (11)
C10	0.2205 (8)	1.0845 (7)	0.9156 (4)	0.0225 (6)	0.849 (4)
C11	0.2332 (7)	1.1590 (6)	0.7828 (4)	0.0244 (6)	0.849 (4)
H11	0.3220	1.1028	0.7156	0.029*	0.849 (4)
C12	0.1151 (9)	1.3139 (6)	0.7527 (4)	0.0261 (8)	0.849 (4)
H12	0.1213	1.3665	0.6640	0.031*	0.849 (4)
C13	−0.0141 (7)	1.3939 (6)	0.8530 (5)	0.0266 (8)	0.849 (4)
H13	−0.0947	1.5025	0.8346	0.032*	0.849 (4)
C14	−0.0216 (10)	1.3109 (6)	0.9799 (5)	0.0278 (11)	0.849 (4)
H14	−0.1139	1.3635	1.0479	0.033*	0.849 (4)
C20	0.3509 (5)	0.8393 (4)	1.0685 (3)	0.0207 (6)	0.849 (4)
C21	0.4837 (8)	0.6828 (6)	1.0816 (3)	0.0257 (7)	0.849 (4)
H21	0.5681	0.6408	1.0064	0.031*	0.849 (4)
C22	0.4909 (8)	0.5907 (6)	1.2041 (5)	0.0301 (9)	0.849 (4)
H22	0.5802	0.4846	1.2147	0.036*	0.849 (4)
C23	0.3637 (13)	0.6561 (8)	1.3131 (4)	0.0308 (10)	0.849 (4)
H23	0.3668	0.5941	1.3986	0.037*	0.849 (4)
C24	0.2358 (11)	0.8085 (7)	1.2967 (5)	0.0288 (10)	0.849 (4)
H24	0.1493	0.8514	1.3710	0.035*	0.849 (4)
N1	0.34303 (19)	0.93048 (15)	0.94688 (12)	0.0249 (3)	0.849 (4)
N2	0.0942 (6)	1.1600 (5)	1.0127 (3)	0.0256 (7)	0.849 (4)
N3	0.2304 (3)	0.8996 (2)	1.1757 (2)	0.0246 (4)	0.849 (4)
C10'	0.128 (3)	1.142 (2)	0.9875 (16)	0.014 (3)	0.151 (4)
C11'	−0.006 (5)	1.300 (3)	0.993 (3)	0.027 (6)	0.151 (4)
H11'	−0.0692	1.3389	1.0734	0.032*	0.151 (4)
C12'	−0.039 (4)	1.393 (3)	0.874 (3)	0.031 (6)	0.151 (4)
H12'	−0.1457	1.4892	0.8698	0.037*	0.151 (4)
C13'	0.086 (5)	1.344 (4)	0.761 (3)	0.028 (5)	0.151 (4)
H13'	0.0771	1.4139	0.6789	0.033*	0.151 (4)
C14'	0.224 (5)	1.193 (3)	0.766 (2)	0.035 (7)	0.151 (4)
H14'	0.3072	1.1601	0.6874	0.042*	0.151 (4)
C20'	0.2608 (17)	0.8922 (14)	1.1419 (12)	0.015 (2)*	0.151 (4)
C21'	0.239 (5)	0.834 (3)	1.277 (2)	0.027 (5)	0.151 (4)
H21'	0.1522	0.9020	1.3373	0.032*	0.151 (4)
C22'	0.342 (8)	0.678 (4)	1.322 (3)	0.031 (6)	0.151 (4)
H22'	0.3267	0.6313	1.4117	0.037*	0.151 (4)
C23'	0.473 (5)	0.595 (4)	1.223 (2)	0.029 (6)*	0.151 (4)
H23'	0.5520	0.4883	1.2485	0.035*	0.151 (4)
C24'	0.494 (5)	0.657 (3)	1.094 (2)	0.039 (7)	0.151 (4)
H24'	0.5823	0.5900	1.0336	0.047*	0.151 (4)
N1'	0.1391 (10)	1.0498 (9)	1.1105 (7)	0.0230 (17)	0.151 (4)
H1'	0.057 (2)	1.0977 (14)	1.1800 (17)	0.028*	0.151 (4)
N2'	0.242 (3)	1.093 (3)	0.8814 (14)	0.019 (3)	0.151 (4)
H4'	0.322 (4)	1.004 (4)	0.8843 (14)	0.022*	0.151 (4)
N3'	0.394 (2)	0.812 (2)	1.0473 (17)	0.026 (4)	0.151 (4)
H1	0.432 (4)	0.883 (3)	0.881 (2)	0.043 (6)*	0.849 (4)
H4	0.159 (4)	0.990 (5)	1.153 (3)	0.047 (9)*	0.849 (4)
H2	0.987 (4)	0.718 (3)	0.596 (2)	0.050 (6)*
H3	0.458 (4)	0.768 (3)	0.581 (2)	0.058 (6)*
H5	0.691 (3)	0.942 (3)	0.566 (2)	0.049 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0353 (5)	0.0543 (7)	0.0291 (5)	−0.0037 (5)	−0.0046 (4)	−0.0152 (5)
O2	0.0280 (5)	0.0522 (7)	0.0353 (5)	−0.0081 (5)	−0.0012 (4)	−0.0150 (5)
O3	0.0323 (5)	0.0625 (8)	0.0306 (5)	−0.0161 (5)	−0.0036 (4)	−0.0131 (5)
P	0.02755 (17)	0.02780 (18)	0.02729 (18)	−0.00683 (13)	−0.00472 (12)	−0.00305 (12)
Cl	0.02738 (17)	0.0477 (2)	0.03562 (19)	−0.01126 (14)	−0.00377 (13)	−0.00609 (15)
C10	0.0268 (13)	0.0255 (10)	0.0168 (15)	−0.0124 (9)	−0.0034 (12)	−0.0006 (13)
C11	0.0291 (11)	0.0216 (15)	0.0204 (14)	−0.0065 (10)	−0.0037 (10)	−0.0024 (12)
C12	0.033 (2)	0.023 (2)	0.0207 (10)	−0.0057 (16)	−0.0054 (9)	−0.0031 (11)
C13	0.0292 (19)	0.0237 (12)	0.0237 (14)	−0.0054 (10)	−0.0055 (15)	−0.0014 (10)
C14	0.0307 (14)	0.0250 (14)	0.0252 (19)	−0.0042 (10)	−0.0050 (14)	−0.0063 (12)
C20	0.0222 (14)	0.0210 (10)	0.0192 (13)	−0.0076 (9)	−0.0023 (11)	−0.0040 (10)
C21	0.0283 (18)	0.0251 (19)	0.0222 (9)	−0.0082 (14)	−0.0054 (8)	0.0002 (8)
C22	0.0311 (15)	0.0276 (12)	0.0269 (15)	−0.0062 (8)	−0.0063 (12)	0.0012 (11)
C23	0.034 (2)	0.0275 (14)	0.028 (2)	−0.0073 (11)	−0.010 (2)	0.0010 (16)
C24	0.0375 (14)	0.028 (2)	0.0211 (9)	−0.0129 (17)	−0.0060 (8)	0.0007 (11)
N1	0.0284 (6)	0.0253 (6)	0.0177 (6)	−0.0058 (5)	−0.0008 (4)	−0.0046 (4)
N2	0.0294 (14)	0.0254 (11)	0.0207 (11)	−0.0070 (9)	−0.0006 (9)	−0.0077 (8)
N3	0.0279 (8)	0.0242 (8)	0.0195 (8)	−0.0069 (6)	−0.0010 (7)	−0.0048 (7)
C10'	0.019 (7)	0.008 (4)	0.013 (7)	−0.002 (4)	−0.005 (6)	0.000 (5)
C11'	0.037 (11)	0.034 (10)	0.016 (7)	−0.021 (8)	−0.012 (6)	0.008 (5)
C12'	0.022 (6)	0.038 (9)	0.033 (11)	−0.015 (5)	0.017 (5)	−0.024 (8)
C13'	0.023 (8)	0.008 (7)	0.049 (11)	0.005 (5)	−0.017 (7)	−0.003 (5)
C14'	0.058 (13)	0.037 (15)	0.015 (6)	−0.029 (11)	−0.007 (6)	0.009 (6)
C21'	0.025 (7)	0.006 (5)	0.046 (13)	−0.004 (5)	−0.012 (8)	0.004 (6)
C22'	0.034 (11)	0.041 (14)	0.017 (7)	−0.010 (9)	0.011 (6)	−0.021 (8)
C24'	0.028 (8)	0.010 (6)	0.077 (17)	0.008 (5)	−0.025 (9)	−0.008 (8)
N1'	0.027 (3)	0.018 (3)	0.021 (3)	−0.002 (3)	−0.004 (3)	−0.006 (3)
N2'	0.024 (5)	0.014 (4)	0.015 (8)	−0.006 (3)	0.000 (6)	0.002 (6)
N3'	0.024 (7)	0.037 (8)	0.019 (5)	−0.013 (6)	0.012 (4)	−0.023 (4)

Geometric parameters (Å, º)

O1—P	1.473 (1)	N1—H1	0.91 (3)
O2—P	1.552 (1)	N3—H4	0.81 (4)
O2—H2	0.84 (3)	C10'—N2'	1.30 (2)
O3—P	1.556 (1)	C10'—N1'	1.38 (2)
O3—H3	0.89 (3)	C10'—C11'	1.42 (2)
P—H5	1.28 (2)	C11'—C12'	1.37 (2)
C10—N2	1.345 (5)	C11'—H11'	0.95
C10—N1	1.379 (6)	C12'—C13'	1.39 (2)
C10—C11	1.412 (5)	C12'—H12'	0.95
C11—C12	1.370 (5)	C13'—C14'	1.38 (2)
C11—H11	0.95	C13'—H13'	0.95
C12—C13	1.394 (5)	C14'—N2'	1.35 (2)
C12—H12	0.95	C14'—H14'	0.95
C13—C14	1.379 (5)	C20'—N3'	1.36 (1)
C13—H13	0.95	C20'—N1'	1.40 (1)
C14—N2	1.344 (5)	C20'—C21'	1.40 (2)
C14—H14	0.95	C20'—H4	0.94 (4)
C20—N3	1.355 (4)	C21'—C22'	1.37 (2)
C20—N1	1.364 (3)	C21'—H21'	0.95
C20—C21	1.403 (5)	C22'—C23'	1.40 (2)
C21—C22	1.374 (5)	C22'—H22'	0.95
C21—H21	0.95	C23'—C24'	1.35 (2)
C22—C23	1.404 (5)	C23'—H23'	0.95
C22—H22	0.95	C24'—N3'	1.37 (2)
C23—C24	1.364 (6)	C24'—H24'	0.95
C23—H23	0.95	N1'—H1'	0.92
C24—N3	1.357 (5)	N2'—H4'	0.81
C24—H24	0.95
P—O2—H2	111.1 (16)	C20—N3—H4	110 (2)
P—O3—H3	110.3 (17)	C24—N3—H4	130 (2)
O1—P—O2	115.68 (7)	N2'—C10'—N1'	123 (1)
O1—P—O3	115.50 (7)	N2'—C10'—C11'	125 (2)
O2—P—O3	101.06 (7)	N1'—C10'—C11'	112 (2)
O1—P—H5	113 (1)	C12'—C11'—C10'	116 (2)
O2—P—H5	105 (1)	C12'—C11'—H11'	122.1
O3—P—H5	105 (1)	C10'—C11'—H11'	122.1
N2—C10—N1	119.0 (4)	C11'—C12'—C13'	119 (2)
N2—C10—C11	122.0 (5)	C11'—C12'—H12'	120.6
N1—C10—C11	119.1 (4)	C13'—C12'—H12'	120.6
C12—C11—C10	118.8 (4)	C14'—C13'—C12'	120 (2)
C12—C11—H11	120.6	C14'—C13'—H13'	119.8
C10—C11—H11	120.6	C12'—C13'—H13'	119.8
C11—C12—C13	119.6 (3)	N2'—C14'—C13'	121 (2)
C11—C12—H12	120.2	N2'—C14'—H14'	119.6
C13—C12—H12	120.2	C13'—C14'—H14'	119.6
C14—C13—C12	118.1 (3)	N3'—C20'—N1'	121 (1)
C14—C13—H13	121.0	N3'—C20'—C21'	125 (2)
C12—C13—H13	121.0	N1'—C20'—C21'	114 (1)
N2—C14—C13	123.7 (4)	N3'—C20'—H4	142 (2)
N2—C14—H14	118.2	C21'—C20'—H4	93 (3)
C13—C14—H14	118.2	C22'—C21'—C20'	120 (2)
N3—C20—N1	120.1 (2)	C22'—C21'—H21'	120.0
N3—C20—C21	120.4 (3)	C20'—C21'—H21'	120.0
N1—C20—C21	119.5 (3)	C21'—C22'—C23'	114 (2)
C22—C21—C20	119.5 (3)	C21'—C22'—H22'	123.0
C22—C21—H21	120.3	C23'—C22'—H22'	123.0
C20—C21—H21	120.3	C24'—C23'—C22'	124 (2)
C21—C22—C23	118.8 (4)	C24'—C23'—H23'	117.8
C21—C22—H22	120.6	C22'—C23'—H23'	117.8
C23—C22—H22	120.6	C23'—C24'—N3'	123 (2)
C24—C23—C22	120.1 (4)	C23'—C24'—H24'	118.7
C24—C23—H23	119.9	N3'—C24'—H24'	118.7
C22—C23—H23	119.9	C10'—N1'—C20'	128 (1)
N3—C24—C23	120.9 (4)	C10'—N1'—H1'	116.2
N3—C24—H24	119.6	C20'—N1'—H1'	116.2
C23—C24—H24	119.6	C10'—N1'—H4	160 (3)
C20—N1—C10	127.4 (2)	H1'—N1'—H4	83.6
C20—N1—H1	115 (2)	C10'—N2'—C14'	118 (2)
C10—N1—H1	118 (2)	C10'—N2'—H4'	120.8
C10—N2—C14	117.8 (4)	C14'—N2'—H4'	120.8
C20—N3—C24	120.3 (3)	C20'—N3'—C24'	114 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91 (3)	1.82 (3)	2.720 (2)	173 (2)
N3—H4···N2	0.81 (4)	1.89 (4)	2.610 (4)	147 (3)
O2—H2···Cl^i	0.84 (3)	2.13 (3)	2.964 (1)	173 (2)
O3—H3···Cl^ii	0.89 (3)	2.07 (3)	2.954 (1)	176 (2)

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