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The title salt, C7H9ClN+·H2PO4, is monoclinic (P21/c). The ions are held together by O—H...O and N—H...O hydrogen bonds. The O—H...O bonds interconnect the di­hydrogenphosphates into sheets which are parallel to the (100) plane. In each sheet, there are centrosymmetric pairs of di­hydrogenphosphates held together by O—H...O bonds. In addition, the di­hydrogenphosphates are interconnected by —NH3 groups. Each H atom from an —NH3 group is donated to a different di­hydrogenphosphate ion. A differential scanning calorimetry experiment showed no anomaly between 98 and 420 K.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021808/na6121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021808/na6121Isup2.hkl
Contains datablock I

CCDC reference: 180774

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.170
  • Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry
Yellow Alert Alert Level C:
RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.141
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: KM4B8 (Gałdecki et al., 1997); cell refinement: LATCO (Allmann, 1988); data reduction: JANA2000 (Petříček & Dušek, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996).

(I) top
Crystal data top
C7H9ClN+·H2PO4F(000) = 496
Mr = 239.59In the setting corresponding to C1121/b it has nearly orthorhombic setting.
Monoclinic, P21/cDx = 1.497 Mg m3
Hall symbol: -P2ybcMo Kα radiation, λ = 0.710688 Å
a = 16.603 (4) ÅCell parameters from 18 reflections
b = 8.339 (3) Åθ = 2.8–15.8°
c = 7.903 (4) ŵ = 0.50 mm1
β = 103.76 (6)°T = 290 K
V = 1062.8 (7) Å3Plate, colourless
Z = 40.30 × 0.14 × 0.06 mm
Data collection top
Kuma KM-4
diffractometer
Rint = 0.141
ω–2θ scansθmax = 26.3°, θmin = 1.3°
Absorption correction: integration
Gaussian integration (Coppens, 1965)
h = 2020
Tmin = 0.919, Tmax = 0.977k = 100
4283 measured reflectionsl = 99
2151 independent reflections3 standard reflections every 200 reflections
911 reflections with I > 2σ(I) intensity decay: 9.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.1P)2 + ]
where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.001
2151 reflectionsΔρmax = 0.23 e Å3
132 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (3)
Special details top

Experimental. The diffractions of the studied crystals were invariably split except for the diffractions 00 l. No domains, however, were observed in the microscope in the polarized light. Because of this splitting the lattice parameters were determined from the powder pattern. The powder diffractometer used is a locally adapted parallel beam HUBER powder diffractometer equipped with Goebel mirror and double crystal monochromator in reflected beam. The source is rotation-anode (Cu) radiation generated by 55 kV/300 mA; step scan mode with 5 - s step 0.02 ° in 2θ. The data collection was performed in the unit cell with C-centered orthorhombic metric (see the section _publ_section_comment). The parameters of the scan were chosen so the split peaks fell between the background regions, and therefore they were integrated together.

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 (Å2) top
xyzUiso*/Ueq
P10.43529 (8)0.03782 (14)0.20760 (16)0.0370 (4)
O30.52042 (19)0.0964 (4)0.2029 (4)0.0407 (8)
O10.4420 (3)0.1045 (4)0.3391 (5)0.0508 (9)
H10.46100.18340.30030.076*
O20.3906 (2)0.0258 (5)0.0236 (4)0.0537 (10)
H20.42500.04290.03340.081*
O40.3801 (2)0.1578 (4)0.2637 (4)0.0479 (9)
Cl0.02954 (12)0.7927 (3)0.0569 (3)0.1069 (8)
N0.3438 (2)0.4280 (4)0.0670 (5)0.0388 (10)
H1N0.38490.49350.11730.058*
H2N0.35180.39440.03460.058*
H3N0.34280.34400.13600.058*
C10.2655 (3)0.5128 (6)0.0384 (6)0.0403 (12)
C20.1921 (3)0.4343 (6)0.0326 (7)0.0530 (14)
C30.1192 (4)0.5239 (8)0.0615 (8)0.0675 (17)
H30.06870.47490.11080.081*
C40.1210 (4)0.6838 (8)0.0179 (8)0.0659 (17)
C50.1936 (4)0.7599 (8)0.0538 (10)0.0760 (19)
H50.19430.86790.08340.091*
C60.2665 (4)0.6728 (6)0.0817 (8)0.0597 (16)
H60.31670.72280.13030.072*
C70.1901 (4)0.2564 (7)0.0783 (10)0.080 (2)
H1C70.22940.23520.14720.120*
H2C70.13550.22770.14330.120*
H3C70.20420.19420.02680.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0497 (8)0.0241 (6)0.0401 (7)0.0002 (6)0.0162 (5)0.0005 (6)
O30.048 (2)0.0318 (17)0.0438 (19)0.0026 (16)0.0132 (15)0.0031 (14)
O10.080 (3)0.0277 (17)0.052 (2)0.0044 (18)0.0301 (18)0.0022 (15)
O20.049 (2)0.067 (2)0.0457 (19)0.013 (2)0.0132 (16)0.0116 (19)
O40.063 (2)0.0342 (18)0.053 (2)0.0111 (17)0.0264 (18)0.0071 (16)
Cl0.0742 (13)0.1020 (16)0.1401 (18)0.0406 (12)0.0167 (12)0.0085 (13)
N0.047 (2)0.031 (2)0.041 (2)0.0005 (18)0.0144 (18)0.0045 (16)
C10.043 (3)0.037 (3)0.043 (3)0.002 (2)0.015 (2)0.002 (2)
C20.053 (4)0.048 (3)0.057 (3)0.004 (3)0.011 (3)0.001 (3)
C30.053 (4)0.070 (4)0.076 (4)0.003 (3)0.010 (3)0.003 (3)
C40.053 (4)0.071 (4)0.071 (4)0.018 (3)0.010 (3)0.010 (3)
C50.072 (5)0.046 (3)0.108 (5)0.007 (3)0.017 (4)0.006 (4)
C60.052 (4)0.036 (3)0.087 (4)0.003 (3)0.007 (3)0.006 (3)
C70.071 (5)0.053 (4)0.109 (5)0.016 (3)0.009 (4)0.025 (4)
Geometric parameters (Å, º) top
P1—O41.493 (4)C1—C21.379 (7)
P1—O31.504 (3)C2—C31.395 (8)
P1—O21.560 (4)C2—C71.526 (8)
P1—O11.564 (3)C3—C41.376 (9)
O1—H10.8200C3—H30.9300
O2—H20.8200C4—C51.362 (9)
Cl—C41.732 (6)C6—C51.383 (8)
N—C11.449 (6)C6—H60.9300
N—H1N0.8900C5—H50.9300
N—H2N0.8900C7—H1C70.9600
N—H3N0.8900C7—H2C70.9600
C1—C61.376 (7)C7—H3C70.9600
O4—P1—O3115.8 (2)C3—C2—C7120.9 (6)
O4—P1—O2108.4 (2)C4—C3—C2120.8 (6)
O3—P1—O2109.2 (2)C4—C3—H3119.6
O4—P1—O1105.2 (2)C2—C3—H3119.6
O3—P1—O1110.2 (2)C5—C4—C3121.3 (6)
O2—P1—O1107.7 (2)C5—C4—Cl118.8 (5)
P1—O1—H1109.5C3—C4—Cl119.8 (5)
P1—O2—H2109.5C1—C6—C5120.8 (5)
C1—N—H1N109.5C1—C6—H6119.6
C1—N—H2N109.5C5—C6—H6119.6
H1N—N—H2N109.5C4—C5—C6118.5 (6)
C1—N—H3N109.5C4—C5—H5120.8
H1N—N—H3N109.5C6—C5—H5120.8
H2N—N—H3N109.5C2—C7—H1C7109.5
C6—C1—C2121.2 (5)C2—C7—H2C7109.5
C6—C1—N118.5 (5)H1C7—C7—H2C7109.5
C2—C1—N120.3 (4)C2—C7—H3C7109.5
C1—C2—C3117.5 (5)H1C7—C7—H3C7109.5
C1—C2—C7121.7 (5)H2C7—C7—H3C7109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.862.611 (4)151
O2—H2···O3ii0.821.842.644 (5)166
N—H1N···O3iii0.892.042.900 (5)162
N—H2N···O4iv0.891.822.704 (5)173
N—H3N···O40.891.882.722 (5)158
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z1/2.
 

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