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Crystal structure studies in the 100-345 K temperature range were performed to relate the molecular structure changes of meta-carboxyphenylammonium phosphite (m-CPAMP) to its first-order phase transition at Tc = 246 (2) K. Thermal displacement parameters and most bond distances show an abrupt jump at the transition. Such a structural change is related to collective effects leading to competition between intra- and intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108042298/bk5076sup1.cif
Contains datablocks m-CPAMP_100K, m-CPAMP_130K, m-CPAMP_170K, m-CPAMP_210K, m-CPAMP_235K, m-CPAMP_255K, m-CPAMP_293K, m-CPAMP_320K, m-CPAMP_345K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076100Ksup2.fcf
Contains datablock 100K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076130Ksup3.fcf
Contains datablock 130K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076170Ksup4.fcf
Contains datablock 170K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076210Ksup5.fcf
Contains datablock 210K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076235Ksup6.fcf
Contains datablock 235K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076255Ksup7.fcf
Contains datablock 255K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076293Ksup8.fcf
Contains datablock 293K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076320Ksup9.fcf
Contains datablock 320K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108042298/bk5076345Ksup10.fcf
Contains datablock 345K

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108042298/bk5076sup11.pdf
Extra figures and tables

CCDC references: 292332; 292333; 722685; 722686; 722687; 722688; 722689; 722691; 722692

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett,M. N & Johnson, C. K, 1996); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(100K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.535 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 78938 reflections
a = 12.1405 (7) Åθ = 3.4–30.0°
b = 12.4273 (9) ŵ = 0.29 mm1
c = 6.3851 (4) ÅT = 100 K
β = 100.122 (5)°Plate, brown
V = 948.35 (11) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2751 independent reflections
Radiation source: fine-focus sealed tube2731 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 30.0°, θmin = 3.4°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1716
Tmin = 0.908, Tmax = 0.938k = 017
78938 measured reflectionsl = 08
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0599P)2 + 0.3946P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max = 0.026
S = 1.08Δρmax = 0.56 e Å3
2751 reflectionsΔρmin = 0.32 e Å3
165 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 948.35 (11) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1405 (7) ŵ = 0.29 mm1
b = 12.4273 (9) ÅT = 100 K
c = 6.3851 (4) Å0.40 × 0.40 × 0.20 mm
β = 100.122 (5)°
Data collection top
Xcalibur-Saphire2
diffractometer
2751 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2731 reflections with I > 2σ(I)
Tmin = 0.908, Tmax = 0.938Rint = 0.032
78938 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.56 e Å3
2751 reflectionsΔρmin = 0.32 e Å3
165 parameters
Special details top

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
H30.4481 (14)0.4954 (14)0.200 (3)0.020 (4)*
H50.1146 (13)0.5682 (13)0.089 (3)0.017 (4)*
H60.1563 (14)0.7448 (14)0.207 (3)0.020 (4)*
H70.3429 (13)0.8000 (13)0.313 (2)0.013 (3)*
H80.1995 (15)0.4057 (15)0.048 (3)0.025 (4)*
H90.3077 (16)0.3710 (15)0.058 (3)0.026 (4)*
H100.2214 (14)0.3736 (14)0.171 (3)0.022 (4)*
H110.0350 (14)0.2349 (13)0.045 (3)0.019 (4)*
P10.08903 (2)0.148552 (19)0.00442 (4)0.01075 (9)
O30.19991 (6)0.18298 (6)0.05227 (12)0.01362 (15)
O40.09552 (7)0.07376 (6)0.19388 (12)0.01685 (16)
O50.01562 (7)0.09953 (6)0.20055 (12)0.01754 (17)
H120.0263 (15)0.0333 (15)0.187 (3)0.026*
N10.25015 (7)0.40729 (7)0.07221 (14)0.01168 (16)
O10.60643 (6)0.61538 (6)0.35793 (13)0.01649 (16)
O20.55142 (6)0.78693 (6)0.38997 (13)0.01573 (16)
C10.52995 (8)0.69219 (8)0.34391 (15)0.01197 (18)
C20.41256 (8)0.65463 (7)0.27064 (16)0.01128 (18)
C30.38907 (8)0.54785 (8)0.20498 (15)0.01163 (18)
C40.27782 (8)0.51850 (8)0.13834 (15)0.01088 (17)
C50.19020 (8)0.59120 (8)0.13855 (16)0.01305 (18)
C60.21458 (8)0.69674 (8)0.20500 (16)0.01388 (19)
C70.32573 (8)0.72896 (8)0.26893 (15)0.01301 (18)
H10.6753 (14)0.6396 (13)0.414 (3)0.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.00984 (14)0.01082 (14)0.01095 (14)0.00121 (7)0.00005 (9)0.00014 (7)
O30.0100 (3)0.0148 (3)0.0156 (3)0.0015 (2)0.0010 (2)0.0000 (3)
O40.0198 (4)0.0174 (3)0.0116 (3)0.0077 (3)0.0020 (3)0.0022 (3)
O50.0194 (4)0.0180 (4)0.0129 (3)0.0080 (3)0.0036 (3)0.0022 (3)
N10.0111 (4)0.0104 (3)0.0128 (4)0.0008 (3)0.0001 (3)0.0006 (3)
O10.0108 (3)0.0142 (3)0.0226 (4)0.0007 (3)0.0021 (3)0.0009 (3)
O20.0133 (3)0.0136 (3)0.0200 (4)0.0024 (3)0.0021 (3)0.0029 (3)
C10.0116 (4)0.0131 (4)0.0110 (4)0.0008 (3)0.0011 (3)0.0002 (3)
C20.0104 (4)0.0115 (4)0.0115 (4)0.0012 (3)0.0005 (3)0.0001 (3)
C30.0105 (4)0.0115 (4)0.0124 (4)0.0004 (3)0.0007 (3)0.0003 (3)
C40.0112 (4)0.0103 (4)0.0107 (4)0.0010 (3)0.0007 (3)0.0002 (3)
C50.0109 (4)0.0134 (4)0.0144 (4)0.0005 (3)0.0008 (3)0.0006 (3)
C60.0111 (4)0.0142 (4)0.0158 (4)0.0021 (3)0.0008 (3)0.0017 (3)
C70.0130 (4)0.0124 (4)0.0131 (4)0.0002 (3)0.0009 (3)0.0014 (3)
Geometric parameters (Å, º) top
P1—O31.5157 (7)C1—C21.4945 (13)
P1—O41.5165 (8)C2—C71.4002 (13)
P1—O51.5711 (8)C2—C31.4057 (13)
P1—H111.307 (16)C3—C41.3914 (13)
O5—H120.979 (18)C3—H30.973 (17)
N1—C41.4668 (12)C4—C51.3959 (13)
N1—H80.894 (18)C5—C61.3941 (14)
N1—H90.849 (19)C5—H50.960 (16)
N1—H100.880 (18)C6—C71.3980 (13)
O1—C11.3236 (12)C6—H60.928 (17)
O1—H10.902 (17)C7—H70.939 (16)
O2—C11.2303 (12)
O3—P1—O4116.08 (4)C7—C2—C1118.14 (8)
O3—P1—O5107.94 (4)C3—C2—C1121.36 (8)
O4—P1—O5111.67 (4)C4—C3—C2118.28 (9)
O3—P1—H11108.3 (7)C4—C3—H3119.7 (10)
O4—P1—H11107.6 (7)C2—C3—H3122.0 (10)
O5—P1—H11104.6 (7)C3—C4—C5121.94 (9)
P1—O5—H12118.7 (11)C3—C4—N1119.73 (8)
C4—N1—H8110.8 (12)C5—C4—N1118.30 (8)
C4—N1—H9112.3 (12)C6—C5—C4119.22 (9)
H8—N1—H9110.6 (16)C6—C5—H5121.3 (10)
C4—N1—H10110.0 (11)C4—C5—H5119.4 (10)
H8—N1—H10107.8 (15)C5—C6—C7120.05 (9)
H9—N1—H10105.2 (16)C5—C6—H6119.2 (10)
C1—O1—H1112.1 (11)C7—C6—H6120.7 (10)
O2—C1—O1123.87 (9)C6—C7—C2120.00 (9)
O2—C1—C2121.60 (9)C6—C7—H7120.6 (9)
O1—C1—C2114.52 (8)C2—C7—H7119.4 (9)
C7—C2—C3120.49 (9)
O2—C1—C2—C74.22 (14)C2—C3—C4—N1178.96 (8)
O1—C1—C2—C7174.61 (9)C3—C4—C5—C60.77 (15)
O2—C1—C2—C3175.79 (9)N1—C4—C5—C6178.70 (9)
O1—C1—C2—C35.38 (14)C4—C5—C6—C70.47 (15)
C7—C2—C3—C40.13 (14)C5—C6—C7—C21.38 (15)
C1—C2—C3—C4179.88 (9)C3—C2—C7—C61.08 (15)
C2—C3—C4—C51.06 (14)C1—C2—C7—C6178.91 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.98 (2)1.57 (2)2.5456 (11)173 (2)
O(1)—H(1)···O(3)ii0.90 (2)1.70 (2)2.5977 (11)172 (2)
N(1)—H(8)···O(4)iii0.90 (2)1.91 (2)2.7966 (12)171 (2)
N(1)—H(9)···O(2)iv0.85 (2)1.98 (2)2.8097 (12)165 (2)
N(1)—H(10)···O(3)v0.88 (2)1.96 (2)2.8096 (12)162 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(130K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.542 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23422 reflections
a = 12.1342 (7) Åθ = 3.4–30.0°
b = 12.3851 (6) ŵ = 0.29 mm1
c = 6.3821 (4) ÅT = 130 K
β = 100.299 (5)°Plate, brown
V = 943.67 (9) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2732 independent reflections
Radiation source: fine-focus sealed tube2424 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 30.0°, θmin = 3.4°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1717
Tmin = 0.908, Tmax = 0.938k = 1717
23422 measured reflectionsl = 88
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2511P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max = 0.04
S = 1.06Δρmax = 0.44 e Å3
2732 reflectionsΔρmin = 0.29 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 943.67 (9) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1342 (7) ŵ = 0.29 mm1
b = 12.3851 (6) ÅT = 130 K
c = 6.3821 (4) Å0.40 × 0.40 × 0.20 mm
β = 100.299 (5)°
Data collection top
Xcalibur-Saphire2
diffractometer
2732 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2424 reflections with I > 2σ(I)
Tmin = 0.908, Tmax = 0.938Rint = 0.031
23422 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.44 e Å3
2732 reflectionsΔρmin = 0.29 e Å3
167 parameters
Special details top

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
H10.672 (2)0.639 (2)0.414 (4)0.060 (7)*
H30.4505 (13)0.4953 (14)0.204 (3)0.023 (4)*
H50.1121 (13)0.5686 (13)0.086 (3)0.019 (4)*
H60.1555 (14)0.7464 (14)0.203 (3)0.020 (4)*
H70.3452 (13)0.8011 (12)0.314 (2)0.014 (3)*
H80.1985 (15)0.4067 (14)0.051 (3)0.028 (4)*
H90.3094 (15)0.3694 (15)0.058 (3)0.026 (4)*
H100.2210 (14)0.3724 (14)0.168 (3)0.024 (4)*
H120.025 (2)0.030 (2)0.185 (5)0.088 (9)*
H110.0352 (13)0.2343 (13)0.044 (3)0.019 (4)*
P10.08935 (2)0.14824 (2)0.00430 (4)0.01321 (10)
O30.19998 (7)0.18246 (7)0.05174 (13)0.01660 (18)
O40.09564 (8)0.07373 (7)0.19355 (14)0.02064 (19)
O50.01606 (8)0.09916 (7)0.20027 (14)0.0214 (2)
N10.25001 (8)0.40735 (7)0.07251 (16)0.01386 (19)
O10.60624 (7)0.61513 (7)0.35759 (15)0.01996 (19)
O20.55178 (7)0.78684 (7)0.38879 (14)0.01909 (19)
C10.53010 (9)0.69217 (9)0.34328 (18)0.0144 (2)
C20.41289 (9)0.65471 (9)0.26956 (18)0.0136 (2)
C30.38912 (9)0.54794 (9)0.20472 (17)0.0139 (2)
C40.27801 (9)0.51871 (8)0.13806 (17)0.0131 (2)
C50.19071 (9)0.59162 (9)0.13754 (18)0.0158 (2)
C60.21542 (10)0.69724 (9)0.20325 (19)0.0170 (2)
C70.32632 (9)0.72931 (9)0.26724 (18)0.0157 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01162 (15)0.01337 (15)0.01381 (16)0.00144 (9)0.00005 (10)0.00012 (9)
O30.0121 (4)0.0181 (4)0.0189 (4)0.0015 (3)0.0010 (3)0.0002 (3)
O40.0236 (4)0.0215 (4)0.0144 (4)0.0096 (3)0.0028 (3)0.0025 (3)
O50.0235 (4)0.0224 (4)0.0154 (4)0.0100 (3)0.0044 (3)0.0032 (3)
N10.0128 (4)0.0126 (4)0.0153 (5)0.0006 (3)0.0001 (3)0.0006 (3)
O10.0123 (4)0.0176 (4)0.0276 (5)0.0004 (3)0.0029 (3)0.0008 (3)
O20.0155 (4)0.0167 (4)0.0246 (4)0.0029 (3)0.0022 (3)0.0034 (3)
C10.0134 (5)0.0158 (5)0.0135 (5)0.0013 (4)0.0015 (4)0.0001 (4)
C20.0123 (5)0.0144 (5)0.0136 (5)0.0011 (4)0.0006 (4)0.0003 (4)
C30.0122 (5)0.0144 (5)0.0146 (5)0.0004 (4)0.0009 (4)0.0003 (4)
C40.0134 (5)0.0126 (4)0.0129 (5)0.0016 (4)0.0011 (4)0.0001 (4)
C50.0130 (5)0.0166 (5)0.0171 (5)0.0005 (4)0.0008 (4)0.0007 (4)
C60.0139 (5)0.0174 (5)0.0192 (5)0.0028 (4)0.0012 (4)0.0024 (4)
C70.0158 (5)0.0147 (5)0.0158 (5)0.0001 (4)0.0010 (4)0.0017 (4)
Geometric parameters (Å, º) top
P1—O31.5104 (9)C1—C21.4900 (15)
P1—O41.5110 (9)C2—C71.3970 (15)
P1—O51.5651 (9)C2—C31.4001 (15)
P1—H111.301 (16)C3—C41.3873 (15)
O5—H121.00 (3)C3—H30.990 (17)
N1—C41.4636 (14)C4—C51.3915 (15)
N1—H80.916 (18)C5—C61.3899 (16)
N1—H90.879 (18)C5—H50.994 (16)
N1—H100.870 (18)C6—C71.3925 (15)
O1—C11.3199 (14)C6—H60.947 (17)
O1—H10.86 (2)C7—H70.952 (15)
O2—C11.2252 (13)
O3—P1—O4116.15 (5)C7—C2—C1118.09 (10)
O3—P1—O5107.94 (5)C3—C2—C1121.46 (10)
O4—P1—O5111.69 (5)C4—C3—C2118.34 (10)
O3—P1—H11108.5 (7)C4—C3—H3121.1 (10)
O4—P1—H11107.4 (7)C2—C3—H3120.5 (10)
O5—P1—H11104.4 (7)C3—C4—C5121.94 (10)
P1—O5—H12117.9 (17)C3—C4—N1119.79 (9)
C4—N1—H8110.0 (11)C5—C4—N1118.24 (9)
C4—N1—H9112.4 (11)C6—C5—C4119.14 (10)
H8—N1—H9110.5 (16)C6—C5—H5120.9 (9)
C4—N1—H10111.8 (11)C4—C5—H5119.9 (9)
H8—N1—H10107.4 (15)C5—C6—C7120.13 (10)
H9—N1—H10104.5 (15)C5—C6—H6118.6 (10)
C1—O1—H1111.0 (16)C7—C6—H6121.2 (10)
O2—C1—O1123.88 (10)C6—C7—C2119.99 (10)
O2—C1—C2121.68 (10)C6—C7—H7121.6 (9)
O1—C1—C2114.43 (9)C2—C7—H7118.4 (9)
C7—C2—C3120.44 (10)
O2—C1—C2—C74.35 (17)C2—C3—C4—N1179.01 (10)
O1—C1—C2—C7174.68 (10)C3—C4—C5—C60.79 (17)
O2—C1—C2—C3175.84 (11)N1—C4—C5—C6178.74 (10)
O1—C1—C2—C35.12 (16)C4—C5—C6—C70.41 (18)
C7—C2—C3—C40.19 (17)C5—C6—C7—C21.29 (18)
C1—C2—C3—C4179.98 (10)C3—C2—C7—C60.99 (17)
C2—C3—C4—C51.09 (17)C1—C2—C7—C6178.82 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i1.00 (2)1.54 (2)2.5386 (13)173 (2)
O(1)—H(1)···O(3)ii0.87 (3)1.73 (2)2.5919 (12)172 (2)
N(1)—H(8)···O(4)iii0.90 (2)1.88 (2)2.7916 (14)171 (2)
N(1)—H(9)···O(2)iv0.88 (2)1.95 (2)2.8037 (13)165 (2)
N(1)—H(10)···O(3)v0.88 (2)1.96 (2)2.8066 (13)160 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(170K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.536 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23509 reflections
a = 12.1740 (7) Åθ = 3.4–30.0°
b = 12.3719 (6) ŵ = 0.29 mm1
c = 6.3995 (4) ÅT = 170 K
β = 100.535 (5)°Plate, brown
V = 947.62 (9) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2739 independent reflections
Radiation source: fine-focus sealed tube2382 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 30.0°, θmin = 3.4°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1717
Tmin = 0.890, Tmax = 0.942k = 1717
23509 measured reflectionsl = 89
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.066P)2 + 0.2168P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100(Δ/σ)max = 0.034
S = 1.04Δρmax = 0.41 e Å3
2739 reflectionsΔρmin = 0.27 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 947.62 (9) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.1740 (7) ŵ = 0.29 mm1
b = 12.3719 (6) ÅT = 170 K
c = 6.3995 (4) Å0.40 × 0.40 × 0.20 mm
β = 100.535 (5)°
Data collection top
Xcalibur-Saphire2
diffractometer
2739 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2382 reflections with I > 2σ(I)
Tmin = 0.890, Tmax = 0.942Rint = 0.031
23509 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.41 e Å3
2739 reflectionsΔρmin = 0.27 e Å3
167 parameters
Special details top

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
H10.670 (2)0.639 (2)0.411 (4)0.058 (7)*
H30.4511 (14)0.4950 (15)0.205 (3)0.029 (4)*
H50.1131 (14)0.5691 (14)0.082 (3)0.025 (4)*
H60.1565 (14)0.7486 (15)0.200 (3)0.026 (4)*
H70.3466 (13)0.8029 (13)0.309 (2)0.018 (4)*
H80.1977 (15)0.4078 (14)0.053 (3)0.029 (4)*
H90.3095 (16)0.3702 (15)0.059 (3)0.031 (5)*
H100.2207 (15)0.3736 (14)0.168 (3)0.026 (4)*
H120.025 (3)0.032 (3)0.184 (5)0.100 (10)*
H110.0361 (14)0.2328 (13)0.045 (3)0.024 (4)*
P10.08994 (2)0.14772 (2)0.00395 (5)0.01641 (10)
O30.20025 (7)0.18164 (7)0.05116 (14)0.02064 (19)
O40.09597 (8)0.07365 (8)0.19315 (14)0.0257 (2)
O50.01689 (8)0.09845 (8)0.20032 (15)0.0271 (2)
N10.24993 (9)0.40759 (8)0.07289 (17)0.0169 (2)
O10.60597 (8)0.61480 (8)0.35676 (16)0.0248 (2)
O20.55244 (7)0.78673 (7)0.38720 (16)0.0238 (2)
C10.53042 (10)0.69208 (9)0.34211 (19)0.0177 (2)
C20.41333 (10)0.65497 (9)0.26790 (19)0.0166 (2)
C30.38913 (9)0.54804 (9)0.20416 (18)0.0170 (2)
C40.27816 (9)0.51904 (9)0.13733 (18)0.0160 (2)
C50.19156 (10)0.59251 (10)0.1356 (2)0.0195 (2)
C60.21656 (10)0.69827 (10)0.2001 (2)0.0214 (2)
C70.32729 (10)0.73001 (10)0.26422 (19)0.0197 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01448 (16)0.01658 (16)0.01699 (17)0.00195 (9)0.00025 (11)0.00002 (10)
O30.0150 (4)0.0221 (4)0.0238 (4)0.0019 (3)0.0009 (3)0.0002 (3)
O40.0299 (5)0.0269 (4)0.0173 (4)0.0125 (4)0.0038 (3)0.0030 (3)
O50.0297 (5)0.0284 (5)0.0191 (4)0.0136 (4)0.0063 (4)0.0042 (4)
N10.0158 (5)0.0154 (4)0.0184 (5)0.0010 (3)0.0003 (4)0.0008 (3)
O10.0153 (4)0.0214 (4)0.0346 (5)0.0004 (3)0.0040 (4)0.0010 (4)
O20.0190 (4)0.0203 (4)0.0312 (5)0.0039 (3)0.0025 (4)0.0045 (3)
C10.0166 (5)0.0192 (5)0.0167 (5)0.0016 (4)0.0017 (4)0.0001 (4)
C20.0149 (5)0.0174 (5)0.0166 (5)0.0016 (4)0.0004 (4)0.0003 (4)
C30.0152 (5)0.0172 (5)0.0178 (5)0.0009 (4)0.0009 (4)0.0004 (4)
C40.0161 (5)0.0156 (5)0.0155 (5)0.0018 (4)0.0007 (4)0.0002 (4)
C50.0157 (5)0.0205 (5)0.0211 (6)0.0006 (4)0.0005 (4)0.0010 (4)
C60.0176 (5)0.0213 (5)0.0240 (6)0.0039 (4)0.0007 (4)0.0034 (4)
C70.0202 (6)0.0176 (5)0.0202 (5)0.0004 (4)0.0008 (4)0.0025 (4)
Geometric parameters (Å, º) top
P1—O31.5089 (9)C1—C21.4902 (16)
P1—O41.5095 (9)C2—C71.3967 (16)
P1—O51.5640 (9)C2—C31.3998 (16)
P1—H111.293 (16)C3—C41.3876 (15)
O5—H120.98 (3)C3—H30.999 (18)
N1—C41.4620 (14)C4—C51.3905 (16)
N1—H80.933 (18)C5—C61.3890 (17)
N1—H90.877 (19)C5—H50.997 (17)
N1—H100.865 (18)C6—C71.3919 (17)
O1—C11.3181 (14)C6—H60.961 (18)
O1—H10.85 (2)C7—H70.962 (16)
O2—C11.2240 (14)
O3—P1—O4116.20 (5)C7—C2—C1118.13 (10)
O3—P1—O5107.90 (5)C3—C2—C1121.47 (10)
O4—P1—O5111.75 (5)C4—C3—C2118.38 (10)
O3—P1—H11109.1 (7)C4—C3—H3121.6 (10)
O4—P1—H11106.4 (7)C2—C3—H3120.0 (10)
O5—P1—H11104.9 (7)C3—C4—C5121.83 (10)
P1—O5—H12117.5 (19)C3—C4—N1119.74 (10)
C4—N1—H8109.3 (11)C5—C4—N1118.39 (10)
C4—N1—H9111.7 (12)C6—C5—C4119.27 (11)
H8—N1—H9111.1 (16)C6—C5—H5121.3 (10)
C4—N1—H10111.4 (11)C4—C5—H5119.4 (10)
H8—N1—H10107.8 (15)C5—C6—C7120.07 (11)
H9—N1—H10105.4 (16)C5—C6—H6119.0 (10)
C1—O1—H1110.9 (16)C7—C6—H6120.9 (10)
O2—C1—O1123.87 (11)C6—C7—C2120.03 (11)
O2—C1—C2121.69 (10)C6—C7—H7121.5 (9)
O1—C1—C2114.44 (10)C2—C7—H7118.4 (9)
C7—C2—C3120.40 (11)
O2—C1—C2—C74.23 (18)C2—C3—C4—N1179.04 (10)
O1—C1—C2—C7174.95 (11)C3—C4—C5—C60.74 (18)
O2—C1—C2—C3176.04 (12)N1—C4—C5—C6178.79 (11)
O1—C1—C2—C34.78 (17)C4—C5—C6—C70.45 (19)
C7—C2—C3—C40.14 (18)C5—C6—C7—C21.31 (19)
C1—C2—C3—C4179.86 (11)C3—C2—C7—C61.02 (19)
C2—C3—C4—C51.02 (18)C1—C2—C7—C6178.71 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.98 (4)1.56 (4)2.5390 (14)173 (2)
O(1)—H(1)···O(3)ii0.85 (3)1.75 (2)2.5930 (13)172 (2)
N(1)—H(8)···O(4)iii0.93 (2)1.87 (2)2.7941 (14)173 (2)
N(1)—H(9)···O(2)iv0.88 (2)1.95 (2)2.8045 (14)165 (2)
N(1)—H(10)···O(3)v0.88 (2)1.98 (2)2.8116 (12)160 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(210K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.535 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23560 reflections
a = 12.2065 (7) Åθ = 3.4–30.0°
b = 12.3367 (7) ŵ = 0.29 mm1
c = 6.4102 (4) ÅT = 210 K
β = 100.798 (5)°Plate, brown
V = 948.21 (10) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2747 independent reflections
Radiation source: fine-focus sealed tube2346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 30.0°, θmin = 3.4°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1717
Tmin = 0.887, Tmax = 0.935k = 1717
23560 measured reflectionsl = 98
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0722P)2 + 0.0793P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107(Δ/σ)max = 0.031
S = 1.08Δρmax = 0.39 e Å3
2747 reflectionsΔρmin = 0.25 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 948.21 (10) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.2065 (7) ŵ = 0.29 mm1
b = 12.3367 (7) ÅT = 210 K
c = 6.4102 (4) Å0.40 × 0.40 × 0.20 mm
β = 100.798 (5)°
Data collection top
Xcalibur-Saphire2
diffractometer
2747 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2346 reflections with I > 2σ(I)
Tmin = 0.887, Tmax = 0.935Rint = 0.032
23560 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.39 e Å3
2747 reflectionsΔρmin = 0.25 e Å3
167 parameters
Special details top

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
H10.670 (2)0.637 (2)0.407 (4)0.063 (7)*
H30.4519 (14)0.4944 (14)0.203 (3)0.032 (4)*
H50.1134 (14)0.5699 (14)0.080 (3)0.030 (4)*
H60.1595 (14)0.7510 (15)0.193 (3)0.033 (4)*
H70.3467 (12)0.8037 (12)0.305 (2)0.020 (4)*
H80.1967 (14)0.4065 (14)0.055 (3)0.033 (4)*
H100.2190 (14)0.3735 (13)0.172 (3)0.028 (4)*
H90.3095 (16)0.3690 (15)0.060 (3)0.036 (5)*
H110.0359 (13)0.2317 (13)0.044 (3)0.026 (4)*
H120.022 (3)0.031 (3)0.185 (5)0.111 (11)*
P10.09072 (2)0.14711 (2)0.00333 (5)0.01986 (11)
O30.20068 (7)0.18070 (7)0.05062 (15)0.0248 (2)
O40.09641 (8)0.07358 (8)0.19270 (15)0.0310 (2)
O50.01826 (9)0.09736 (8)0.20040 (16)0.0334 (2)
N10.24964 (9)0.40797 (8)0.07301 (18)0.0206 (2)
O10.60564 (8)0.61442 (8)0.35609 (17)0.0300 (2)
O20.55321 (8)0.78672 (7)0.38543 (16)0.0287 (2)
C10.53074 (10)0.69214 (9)0.34069 (19)0.0211 (2)
C20.41380 (10)0.65549 (9)0.26596 (19)0.0200 (2)
C30.38913 (9)0.54832 (9)0.20321 (19)0.0202 (2)
C40.27839 (9)0.51969 (9)0.13620 (18)0.0190 (2)
C50.19246 (10)0.59376 (10)0.1330 (2)0.0236 (3)
C60.21798 (11)0.69967 (10)0.1957 (2)0.0261 (3)
C70.32846 (10)0.73101 (10)0.2606 (2)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01713 (17)0.02028 (17)0.02058 (18)0.00251 (10)0.00055 (12)0.00010 (10)
O30.0176 (4)0.0268 (4)0.0286 (5)0.0024 (3)0.0008 (3)0.0001 (4)
O40.0355 (5)0.0329 (5)0.0206 (5)0.0151 (4)0.0047 (4)0.0035 (4)
O50.0362 (5)0.0360 (5)0.0226 (5)0.0172 (4)0.0078 (4)0.0056 (4)
N10.0187 (5)0.0190 (5)0.0226 (5)0.0008 (4)0.0002 (4)0.0009 (4)
O10.0183 (4)0.0255 (4)0.0420 (6)0.0005 (3)0.0051 (4)0.0012 (4)
O20.0228 (5)0.0242 (4)0.0380 (5)0.0049 (3)0.0029 (4)0.0056 (4)
C10.0191 (5)0.0230 (5)0.0203 (6)0.0016 (4)0.0013 (4)0.0001 (4)
C20.0177 (5)0.0206 (5)0.0204 (6)0.0012 (4)0.0001 (4)0.0007 (4)
C30.0172 (5)0.0205 (5)0.0218 (6)0.0008 (4)0.0010 (4)0.0002 (4)
C40.0186 (5)0.0189 (5)0.0183 (5)0.0013 (4)0.0005 (4)0.0004 (4)
C50.0184 (5)0.0249 (6)0.0261 (6)0.0006 (4)0.0005 (4)0.0019 (4)
C60.0209 (6)0.0256 (6)0.0301 (7)0.0055 (5)0.0004 (5)0.0047 (5)
C70.0235 (6)0.0209 (5)0.0244 (6)0.0005 (4)0.0006 (5)0.0030 (4)
Geometric parameters (Å, º) top
P1—O31.5056 (9)C1—C21.4884 (16)
P1—O41.5066 (10)C2—C71.3931 (17)
P1—O51.5594 (10)C2—C31.3983 (16)
P1—H111.292 (16)C3—C41.3853 (16)
O5—H120.97 (3)C3—H31.015 (17)
N1—C41.4606 (15)C4—C51.3883 (16)
N1—H80.945 (18)C5—C61.3853 (18)
N1—H90.892 (19)C5—H51.006 (17)
N1—H100.902 (18)C6—C71.3895 (17)
O1—C11.3157 (15)C6—H60.953 (18)
O1—H10.84 (2)C7—H70.955 (15)
O2—C11.2205 (14)
O3—P1—O4116.25 (6)C7—C2—C1118.19 (10)
O3—P1—O5107.83 (6)C3—C2—C1121.44 (10)
O4—P1—O5111.78 (5)C4—C3—C2118.38 (11)
O3—P1—H11109.9 (7)C4—C3—H3121.7 (10)
O4—P1—H11105.8 (7)C2—C3—H3119.9 (10)
O5—P1—H11104.6 (7)C3—C4—C5121.83 (11)
P1—O5—H12118 (2)C3—C4—N1119.76 (10)
C4—N1—H8110.4 (11)C5—C4—N1118.39 (10)
C4—N1—H9112.1 (12)C6—C5—C4119.23 (11)
C4—N1—H10111.1 (10)C6—C5—H5121.6 (10)
H8—N1—H9110.2 (16)C4—C5—H5119.1 (10)
H8—N1—H10107.3 (15)C5—C6—C7120.15 (11)
H9—N1—H10105.6 (15)C5—C6—H6119.7 (11)
C1—O1—H1111.6 (17)C7—C6—H6120.2 (11)
O2—C1—O1123.82 (11)C6—C7—C2120.04 (11)
O2—C1—C2121.72 (11)C6—C7—H7120.7 (9)
O1—C1—C2114.45 (10)C2—C7—H7119.3 (9)
C7—C2—C3120.37 (11)
O2—C1—C2—C74.02 (19)C2—C3—C4—N1178.97 (11)
O1—C1—C2—C7175.19 (11)C3—C4—C5—C60.89 (19)
O2—C1—C2—C3176.23 (12)N1—C4—C5—C6178.95 (12)
O1—C1—C2—C34.56 (18)C4—C5—C6—C70.1 (2)
C7—C2—C3—C40.01 (18)C5—C6—C7—C21.0 (2)
C1—C2—C3—C4179.74 (11)C3—C2—C7—C61.0 (2)
C2—C3—C4—C50.93 (18)C1—C2—C7—C6178.79 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.97 (4)1.57 (4)2.5367 (14)173 (2)
O(1)—H(1)···O(3)ii0.84 (3)1.76 (2)2.5900 (14)172 (2)
N(1)—H(8)···O(4)iii0.95 (2)1.85 (2)2.7901 (15)171 (2)
N(1)—H(9)···O(2)iv0.89 (2)1.93 (2)2.8035 (12)165 (2)
N(1)—H(10)···O(3)v0.90 (2)1.96 (2)2.8133 (15)160 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(235K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.527 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23700 reflections
a = 12.2487 (9) Åθ = 3.4–30.0°
b = 12.3265 (8) ŵ = 0.29 mm1
c = 6.4290 (5) ÅT = 235 K
β = 100.981 (6)°Plate, brown
V = 952.90 (12) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2765 independent reflections
Radiation source: fine-focus sealed tube2311 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 30.0°, θmin = 3.4°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1717
Tmin = 0.889, Tmax = 0.940k = 1717
23700 measured reflectionsl = 98
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039 w = 1/[σ2(Fo2) + (0.0777P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max = 0.029
S = 1.10Δρmax = 0.46 e Å3
2765 reflectionsΔρmin = 0.27 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 952.90 (12) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.2487 (9) ŵ = 0.29 mm1
b = 12.3265 (8) ÅT = 235 K
c = 6.4290 (5) Å0.40 × 0.40 × 0.20 mm
β = 100.981 (6)°
Data collection top
Xcalibur-Saphire2
diffractometer
2765 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2311 reflections with I > 2σ(I)
Tmin = 0.889, Tmax = 0.940Rint = 0.033
23700 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.46 e Å3
2765 reflectionsΔρmin = 0.27 e Å3
167 parameters
Special details top

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
H10.6667 (19)0.6370 (17)0.403 (4)0.056 (6)*
H30.4516 (14)0.4936 (15)0.204 (3)0.043 (5)*
H50.1131 (14)0.5692 (15)0.074 (3)0.038 (4)*
H60.1611 (14)0.7524 (15)0.195 (3)0.037 (4)*
H70.3467 (12)0.8045 (12)0.303 (2)0.021 (4)*
H80.1973 (14)0.4082 (13)0.058 (3)0.034 (4)*
H90.3083 (16)0.3676 (14)0.061 (3)0.039 (5)*
H100.2181 (13)0.3735 (13)0.173 (3)0.030 (4)*
H120.020 (3)0.033 (3)0.184 (5)0.120 (11)*
H110.0360 (12)0.2313 (12)0.041 (2)0.026 (4)*
P10.09136 (3)0.14663 (2)0.00270 (5)0.02236 (12)
O30.20098 (7)0.18003 (7)0.05017 (15)0.0276 (2)
O40.09670 (9)0.07350 (8)0.19221 (15)0.0346 (2)
O50.01936 (9)0.09658 (9)0.20068 (16)0.0377 (3)
N10.24952 (9)0.40822 (8)0.07301 (18)0.0230 (2)
O10.60532 (8)0.61408 (8)0.35557 (18)0.0335 (2)
O20.55380 (8)0.78678 (7)0.38396 (17)0.0321 (2)
C10.53100 (10)0.69215 (9)0.3395 (2)0.0237 (2)
C20.41422 (10)0.65590 (9)0.2642 (2)0.0223 (2)
C30.38899 (10)0.54859 (10)0.20249 (19)0.0224 (2)
C40.27857 (10)0.52009 (9)0.13543 (19)0.0212 (2)
C50.19305 (10)0.59481 (10)0.1307 (2)0.0262 (3)
C60.21920 (11)0.70094 (11)0.1925 (2)0.0293 (3)
C70.32925 (11)0.73192 (10)0.2573 (2)0.0264 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01911 (18)0.02290 (18)0.02319 (19)0.00300 (10)0.00071 (12)0.00020 (11)
O30.0195 (4)0.0299 (4)0.0319 (5)0.0027 (3)0.0011 (4)0.0002 (4)
O40.0393 (6)0.0368 (5)0.0232 (5)0.0171 (4)0.0051 (4)0.0037 (4)
O50.0410 (6)0.0414 (6)0.0248 (5)0.0205 (5)0.0087 (4)0.0062 (4)
N10.0206 (5)0.0214 (5)0.0251 (6)0.0009 (4)0.0009 (4)0.0009 (4)
O10.0205 (5)0.0285 (5)0.0468 (6)0.0006 (4)0.0061 (4)0.0015 (4)
O20.0248 (5)0.0267 (4)0.0434 (6)0.0054 (4)0.0031 (4)0.0061 (4)
C10.0216 (5)0.0250 (6)0.0232 (6)0.0021 (4)0.0011 (4)0.0000 (4)
C20.0197 (5)0.0230 (5)0.0229 (6)0.0014 (4)0.0005 (4)0.0000 (4)
C30.0193 (5)0.0227 (5)0.0238 (6)0.0009 (4)0.0008 (4)0.0001 (4)
C40.0203 (5)0.0215 (5)0.0204 (5)0.0016 (4)0.0002 (4)0.0005 (4)
C50.0204 (6)0.0277 (6)0.0288 (7)0.0010 (4)0.0001 (5)0.0028 (5)
C60.0238 (6)0.0285 (6)0.0335 (7)0.0064 (5)0.0001 (5)0.0051 (5)
C70.0265 (6)0.0231 (6)0.0277 (6)0.0011 (5)0.0004 (5)0.0037 (5)
Geometric parameters (Å, º) top
P1—O31.5040 (10)C1—C21.4887 (17)
P1—O41.5069 (10)C2—C71.3949 (17)
P1—O51.5585 (10)C2—C31.3985 (16)
P1—H111.294 (15)C3—C41.3843 (16)
O5—H120.94 (3)C3—H31.022 (18)
N1—C41.4610 (15)C4—C51.3908 (16)
N1—H80.954 (17)C5—C61.3868 (18)
N1—H90.893 (19)C5—H51.028 (17)
N1—H100.918 (17)C6—C71.3866 (18)
O1—C11.3152 (15)C6—H60.956 (18)
O1—H10.81 (2)C7—H70.954 (14)
O2—C11.2205 (14)
O3—P1—O4116.32 (6)C7—C2—C1118.27 (11)
O3—P1—O5107.80 (6)C3—C2—C1121.53 (11)
O4—P1—O5111.84 (5)C4—C3—C2118.58 (11)
O3—P1—H11110.2 (7)C4—C3—H3121.4 (10)
O4—P1—H11105.8 (7)C2—C3—H3120.0 (10)
O5—P1—H11104.3 (7)C3—C4—C5121.72 (11)
P1—O5—H12117 (2)C3—C4—N1119.83 (10)
C4—N1—H8109.3 (10)C5—C4—N1118.43 (10)
C4—N1—H9113.3 (11)C6—C5—C4119.12 (11)
H8—N1—H9109.8 (15)C6—C5—H5122.9 (10)
C4—N1—H10111.1 (10)C4—C5—H5117.9 (10)
H8—N1—H10108.6 (14)C7—C6—C5120.27 (12)
H9—N1—H10104.7 (15)C7—C6—H6119.7 (10)
C1—O1—H1110.8 (15)C5—C6—H6120.0 (11)
O2—C1—O1123.83 (12)C6—C7—C2120.09 (12)
O2—C1—C2121.72 (11)C6—C7—H7119.9 (9)
O1—C1—C2114.44 (10)C2—C7—H7119.9 (9)
C7—C2—C3120.20 (11)
O2—C1—C2—C73.9 (2)C2—C3—C4—N1179.08 (11)
O1—C1—C2—C7175.41 (12)C3—C4—C5—C60.78 (19)
O2—C1—C2—C3176.46 (12)N1—C4—C5—C6179.07 (12)
O1—C1—C2—C34.28 (19)C4—C5—C6—C70.2 (2)
C7—C2—C3—C40.13 (19)C5—C6—C7—C21.1 (2)
C1—C2—C3—C4179.56 (11)C3—C2—C7—C61.1 (2)
C2—C3—C4—C50.81 (19)C1—C2—C7—C6178.62 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.94 (4)1.61 (4)2.5394 (15)173 (2)
O(1)—H(1)···O(3)ii0.81 (2)1.79 (2)2.5931 (14)172 (2)
N(1)—H(8)···O(4)iii0.96 (2)1.84 (2)2.7933 (15)173 (2)
N(1)—H(9)···O(2)iv0.89 (2)1.94 (2)2.8048 (15)165 (2)
N(1)—H(10)···O(3)v0.92 (2)1.96 (2)2.8204 (15)159 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(255K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.511 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25199 reflections
a = 13.0119 (14) Åθ = 3.4–30.0°
b = 11.5643 (13) ŵ = 0.28 mm1
c = 6.6123 (7) ÅT = 255 K
β = 104.433 (9)°Plate, brown
V = 963.57 (18) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2814 independent reflections
Radiation source: fine-focus sealed tube2432 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ω scansθmax = 30.0°, θmin = 3.5°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1818
Tmin = 0.872, Tmax = 0.946k = 1516
25199 measured reflectionsl = 99
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0913P)2 + 0.1968P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.143(Δ/σ)max = 0.062
S = 1.08Δρmax = 0.39 e Å3
2814 reflectionsΔρmin = 0.39 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 963.57 (18) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0119 (14) ŵ = 0.28 mm1
b = 11.5643 (13) ÅT = 255 K
c = 6.6123 (7) Å0.40 × 0.40 × 0.20 mm
β = 104.433 (9)°
Data collection top
Xcalibur-Saphire2
diffractometer
2814 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2432 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.946Rint = 0.056
25199 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.39 e Å3
2814 reflectionsΔρmin = 0.39 e Å3
167 parameters
Special details top

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
H10.673 (4)0.642 (4)0.403 (7)0.142 (18)*
H30.4395 (18)0.500 (2)0.220 (4)0.046 (6)*
H50.1316 (19)0.613 (2)0.020 (3)0.039 (5)*
H60.1903 (16)0.8072 (18)0.101 (3)0.034 (5)*
H70.373 (2)0.845 (2)0.232 (4)0.056 (7)*
H80.194 (2)0.415 (2)0.066 (4)0.054 (7)*
H90.296 (2)0.3679 (19)0.067 (4)0.049 (7)*
H100.2128 (18)0.3940 (19)0.166 (4)0.040 (5)*
H120.011 (3)0.029 (3)0.199 (5)0.093 (11)*
H110.0532 (17)0.2299 (19)0.019 (3)0.039 (5)*
P10.10388 (3)0.13609 (4)0.01814 (6)0.03022 (15)
O30.20965 (8)0.16855 (11)0.05309 (19)0.0370 (3)
O40.10332 (11)0.06916 (13)0.17567 (18)0.0455 (3)
O50.04247 (12)0.06999 (15)0.21812 (19)0.0535 (4)
N10.24362 (10)0.42220 (12)0.0667 (2)0.0301 (3)
O10.59874 (9)0.61054 (11)0.3554 (2)0.0404 (3)
O20.56657 (10)0.79956 (11)0.3718 (2)0.0434 (3)
C10.53603 (11)0.70140 (13)0.3259 (2)0.0297 (3)
C20.42134 (11)0.67560 (13)0.2358 (2)0.0274 (3)
C30.38725 (11)0.56238 (13)0.1924 (2)0.0282 (3)
C40.27973 (11)0.54135 (13)0.1130 (2)0.0279 (3)
C50.20578 (12)0.63065 (14)0.0785 (3)0.0324 (3)
C60.24104 (13)0.74361 (15)0.1209 (3)0.0351 (3)
C70.34869 (13)0.76646 (14)0.1989 (2)0.0319 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0230 (2)0.0361 (2)0.0296 (2)0.00443 (13)0.00286 (15)0.00206 (13)
O30.0234 (5)0.0450 (6)0.0406 (6)0.0062 (4)0.0041 (4)0.0019 (5)
O40.0444 (7)0.0592 (8)0.0273 (6)0.0250 (6)0.0017 (5)0.0029 (5)
O50.0502 (8)0.0772 (11)0.0284 (6)0.0348 (7)0.0010 (5)0.0021 (6)
N10.0249 (6)0.0333 (6)0.0299 (6)0.0032 (5)0.0026 (5)0.0005 (5)
O10.0270 (5)0.0329 (6)0.0543 (7)0.0018 (4)0.0033 (5)0.0010 (5)
O20.0309 (6)0.0327 (6)0.0630 (8)0.0039 (5)0.0049 (5)0.0062 (5)
C10.0272 (6)0.0306 (7)0.0300 (7)0.0005 (5)0.0044 (5)0.0007 (5)
C20.0258 (6)0.0294 (7)0.0256 (6)0.0003 (5)0.0039 (5)0.0001 (5)
C30.0245 (6)0.0294 (7)0.0288 (6)0.0009 (5)0.0032 (5)0.0016 (5)
C40.0251 (6)0.0322 (7)0.0248 (6)0.0003 (5)0.0031 (5)0.0008 (5)
C50.0239 (7)0.0393 (8)0.0321 (7)0.0032 (5)0.0035 (5)0.0012 (6)
C60.0316 (7)0.0376 (8)0.0338 (7)0.0095 (6)0.0041 (6)0.0029 (6)
C70.0338 (7)0.0311 (7)0.0296 (7)0.0033 (6)0.0056 (5)0.0031 (5)
Geometric parameters (Å, º) top
P1—O31.4990 (11)C1—C21.493 (2)
P1—O41.4987 (13)C2—C31.389 (2)
P1—O51.5635 (14)C2—C71.394 (2)
P1—H111.27 (2)C3—C41.388 (2)
O5—H120.88 (4)C3—H30.97 (2)
N1—C41.4633 (19)C4—C51.391 (2)
N1—H80.95 (3)C5—C61.390 (2)
N1—H90.93 (3)C5—H50.97 (2)
N1—H100.91 (2)C6—C71.392 (2)
O1—C11.3147 (19)C6—H60.97 (2)
O1—H11.00 (5)C7—H70.96 (3)
O2—C11.2159 (19)
O4—P1—O3117.48 (7)C3—C2—C1120.45 (13)
O4—P1—O5111.12 (7)C7—C2—C1119.09 (13)
O3—P1—O5106.70 (8)C4—C3—C2118.89 (13)
O4—P1—H11109.5 (9)C4—C3—H3122.2 (14)
O3—P1—H11106.3 (10)C2—C3—H3118.9 (14)
O5—P1—H11104.9 (9)C3—C4—C5121.52 (14)
P1—O5—H12113 (2)C3—C4—N1119.02 (13)
C4—N1—H8112.8 (16)C5—C4—N1119.46 (13)
C4—N1—H9116.0 (15)C6—C5—C4118.99 (14)
H8—N1—H9105 (2)C6—C5—H5121.9 (14)
C4—N1—H10111.3 (14)C4—C5—H5119.0 (14)
H8—N1—H10108 (2)C5—C6—C7120.29 (14)
H9—N1—H10102 (2)C5—C6—H6120.2 (12)
C1—O1—H1106 (3)C7—C6—H6119.5 (12)
O2—C1—O1123.84 (14)C6—C7—C2119.84 (15)
O2—C1—C2121.22 (14)C6—C7—H7120.1 (16)
O1—C1—C2114.92 (13)C2—C7—H7120.0 (16)
C3—C2—C7120.45 (14)
O2—C1—C2—C71.7 (2)C2—C3—C4—N1179.85 (13)
O1—C1—C2—C7179.98 (14)C3—C4—C5—C61.3 (2)
O2—C1—C2—C3177.26 (15)N1—C4—C5—C6179.32 (14)
O1—C1—C2—C31.0 (2)C4—C5—C6—C70.7 (2)
C7—C2—C3—C40.4 (2)C5—C6—C7—C20.4 (2)
C1—C2—C3—C4178.60 (13)C3—C2—C7—C60.9 (2)
C2—C3—C4—C50.8 (2)C1—C2—C7—C6178.07 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.88 (4)1.69 (4)2.556 (2)173 (2)
O(1)—H(1)···O(3)ii1.01 (5)1.63 (5)2.5977 (11)160 (4)
N(1)—H(8)···O(4)iii0.96 (3)1.83 (3)2.7704 (18)171 (2)
N(1)—H(9)···O(2)iv0.93 (2)1.90 (3)2.7885 (19)159 (2)
N(1)—H(10)···O(3)v0.91 (2)2.00 (3)2.8585 (18)156 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(293K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.508 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 26411 reflections
a = 13.036 (3) Åθ = 4.8–30.0°
b = 11.538 (2) ŵ = 0.28 mm1
c = 6.6366 (13) ÅT = 293 K
β = 104.73 (3)°Plate, brown
V = 965.4 (4) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2807 independent reflections
Radiation source: fine-focus sealed tube2063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 30.0°, θmin = 4.8°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1718
Tmin = 0.896, Tmax = 0.946k = 160
26411 measured reflectionsl = 90
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0639P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.27 e Å3
2807 reflectionsΔρmin = 0.34 e Å3
165 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 965.4 (4) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.036 (3) ŵ = 0.28 mm1
b = 11.538 (2) ÅT = 293 K
c = 6.6366 (13) Å0.40 × 0.40 × 0.20 mm
β = 104.73 (3)°
Data collection top
Xcalibur-Saphire2
diffractometer
2807 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2063 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 0.946Rint = 0.041
26411 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.27 e Å3
2807 reflectionsΔρmin = 0.34 e Å3
165 parameters
Special details top

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
H50.1278 (14)0.6071 (16)0.008 (2)0.050 (5)*
H60.1955 (12)0.8086 (13)0.104 (2)0.035 (4)*
H30.4417 (12)0.5040 (14)0.225 (2)0.044 (4)*
H110.0527 (12)0.2268 (14)0.017 (2)0.048 (4)*
H70.3723 (14)0.8526 (16)0.211 (3)0.058 (5)*
H80.1949 (14)0.4182 (14)0.060 (3)0.049 (4)*
H100.2138 (19)0.3977 (18)0.181 (3)0.082 (6)*
H90.3012 (19)0.3710 (18)0.079 (3)0.080 (7)*
P10.10445 (3)0.13531 (3)0.01752 (6)0.03572 (13)
O30.20964 (7)0.16772 (9)0.05157 (17)0.0454 (3)
O40.10345 (9)0.06901 (10)0.17558 (15)0.0533 (3)
O50.04365 (10)0.06885 (13)0.21676 (16)0.0639 (4)
H120.001 (2)0.016 (2)0.196 (4)0.096*
N10.24297 (9)0.42377 (10)0.0673 (2)0.0358 (3)
O10.59823 (8)0.61087 (9)0.35419 (18)0.0478 (3)
O20.56758 (8)0.80059 (8)0.36805 (19)0.0511 (3)
C10.53616 (10)0.70225 (11)0.3236 (2)0.0345 (3)
C20.42153 (10)0.67703 (11)0.2333 (2)0.0320 (3)
C30.38699 (10)0.56395 (11)0.1909 (2)0.0331 (3)
C40.27981 (10)0.54327 (11)0.11227 (19)0.0324 (3)
C50.20668 (11)0.63335 (12)0.0767 (2)0.0387 (3)
C60.24259 (11)0.74588 (13)0.1175 (2)0.0408 (3)
C70.34918 (11)0.76837 (12)0.1949 (2)0.0373 (3)
H10.6608 (16)0.6387 (15)0.395 (3)0.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.02716 (18)0.0416 (2)0.0360 (2)0.00476 (13)0.00350 (13)0.00284 (14)
O30.0274 (5)0.0541 (6)0.0519 (7)0.0065 (4)0.0049 (4)0.0041 (5)
O40.0521 (6)0.0694 (8)0.0317 (5)0.0281 (5)0.0018 (4)0.0040 (5)
O50.0619 (8)0.0905 (10)0.0334 (6)0.0415 (7)0.0016 (5)0.0026 (5)
N10.0299 (6)0.0391 (6)0.0349 (7)0.0036 (5)0.0019 (5)0.0003 (5)
O10.0315 (5)0.0376 (6)0.0656 (7)0.0022 (4)0.0039 (5)0.0003 (5)
O20.0367 (6)0.0365 (6)0.0750 (8)0.0043 (4)0.0046 (5)0.0064 (5)
C10.0333 (7)0.0346 (7)0.0347 (7)0.0018 (5)0.0067 (5)0.0000 (5)
C20.0304 (6)0.0349 (6)0.0295 (6)0.0015 (5)0.0054 (5)0.0012 (5)
C30.0296 (6)0.0334 (7)0.0335 (7)0.0021 (5)0.0031 (5)0.0020 (5)
C40.0296 (6)0.0368 (7)0.0288 (6)0.0004 (5)0.0040 (5)0.0010 (5)
C50.0288 (6)0.0469 (8)0.0382 (7)0.0039 (5)0.0045 (5)0.0015 (6)
C60.0383 (7)0.0423 (7)0.0394 (7)0.0123 (6)0.0057 (6)0.0025 (6)
C70.0416 (7)0.0352 (7)0.0334 (7)0.0047 (6)0.0067 (5)0.0034 (5)
Geometric parameters (Å, º) top
P1—O31.4931 (11)C1—C21.4905 (18)
P1—O41.4954 (11)C2—C31.3855 (18)
P1—O51.5593 (12)C2—C71.3938 (18)
P1—H111.253 (16)C3—C41.3823 (18)
O5—H120.85 (3)C3—H30.978 (16)
N1—C41.4657 (17)C4—C51.3894 (18)
N1—H80.917 (18)C5—C61.384 (2)
N1—H100.97 (2)C5—H51.058 (18)
N1—H90.96 (2)C6—C71.378 (2)
O1—C11.3130 (16)C6—H60.938 (15)
O1—H10.85 (2)C7—H71.016 (18)
O2—C11.2169 (16)
O3—P1—O4117.80 (6)C3—C2—C1120.41 (11)
O3—P1—O5106.45 (7)C7—C2—C1119.24 (12)
O4—P1—O5111.21 (6)C4—C3—C2118.96 (12)
O3—P1—H11107.8 (7)C4—C3—H3124.9 (9)
O4—P1—H11107.8 (7)C2—C3—H3116.1 (9)
O5—P1—H11105.1 (7)C3—C4—C5121.27 (12)
P1—O5—H12114.9 (17)C3—C4—N1119.12 (11)
C4—N1—H8111.4 (11)C5—C4—N1119.60 (12)
C4—N1—H10107.8 (12)C6—C5—C4119.04 (13)
H8—N1—H10112.3 (18)C6—C5—H5126.6 (10)
C4—N1—H9111.6 (12)C4—C5—H5114.2 (10)
H8—N1—H9111.9 (16)C7—C6—C5120.57 (13)
H10—N1—H9101.3 (17)C7—C6—H6117.6 (9)
C1—O1—H1104.4 (12)C5—C6—H6121.6 (9)
O2—C1—O1123.71 (13)C6—C7—C2119.80 (13)
O2—C1—C2121.38 (12)C6—C7—H7117.6 (10)
O1—C1—C2114.89 (11)C2—C7—H7122.4 (10)
C3—C2—C7120.34 (12)
O2—C1—C2—C3177.61 (14)C2—C3—C4—N1180.00 (12)
O1—C1—C2—C31.0 (2)C3—C4—C5—C61.2 (2)
O2—C1—C2—C71.4 (2)N1—C4—C5—C6179.27 (12)
O1—C1—C2—C7179.99 (12)C4—C5—C6—C70.8 (2)
C7—C2—C3—C40.6 (2)C5—C6—C7—C20.3 (2)
C1—C2—C3—C4178.32 (12)C3—C2—C7—C61.0 (2)
C2—C3—C4—C50.5 (2)C1—C2—C7—C6177.97 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.86 (3)1.71 (3)2.5590 (19)168 (3)
O(1)—H(1)···O(3)ii0.85 (2)1.78 (3)2.5982 (16)161 (2)
N(1)—H(8)···O(4)iii0.92 (2)1.86 (2)2.7693 (17)171 (2)
N(1)—H(9)···O(2)iv0.96 (2)1.84 (3)2.7865 (17)166 (2)
N(1)—H(10)···O(3)v0.97 (3)1.94 (3)2.8740 (18)159 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(320K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.509 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 21224 reflections
a = 13.0363 (8) Åθ = 3.4–30.0°
b = 11.5204 (7) ŵ = 0.28 mm1
c = 6.6446 (5) ÅT = 320 K
β = 104.826 (6)°Plate, brown
V = 964.69 (11) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2816 independent reflections
Radiation source: fine-focus sealed tube2243 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 30.0°, θmin = 3.6°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1818
Tmin = 0.901, Tmax = 0.943k = 1616
21224 measured reflectionsl = 98
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0944P)2 + 0.0131P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149(Δ/σ)max = 0.009
S = 1.14Δρmax = 0.53 e Å3
2816 reflectionsΔρmin = 0.28 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 964.69 (11) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0363 (8) ŵ = 0.28 mm1
b = 11.5204 (7) ÅT = 320 K
c = 6.6446 (5) Å0.40 × 0.40 × 0.20 mm
β = 104.826 (6)°
Data collection top
Xcalibur-Saphire2
diffractometer
2816 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2243 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.943Rint = 0.035
21224 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.149H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.53 e Å3
2816 reflectionsΔρmin = 0.28 e Å3
167 parameters
Special details top

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
H10.668 (3)0.647 (3)0.393 (6)0.132 (14)*
H30.4401 (15)0.5060 (17)0.221 (3)0.041 (5)*
H50.1291 (19)0.6114 (19)0.015 (3)0.049 (5)*
H60.1937 (15)0.8151 (16)0.100 (3)0.038 (5)*
H70.375 (2)0.851 (2)0.223 (4)0.067 (7)*
H80.1937 (18)0.420 (2)0.066 (4)0.055 (6)*
H90.297 (3)0.375 (2)0.072 (4)0.084 (9)*
H100.211 (2)0.400 (2)0.163 (4)0.064 (7)*
H120.008 (3)0.019 (3)0.195 (5)0.109 (11)*
H110.0519 (17)0.2304 (18)0.026 (3)0.052 (6)*
P10.10470 (3)0.13499 (4)0.01712 (6)0.03810 (17)
O30.20999 (9)0.16725 (12)0.0507 (2)0.0486 (3)
O40.10345 (11)0.06893 (13)0.17557 (18)0.0570 (4)
O50.04403 (12)0.06834 (16)0.2163 (2)0.0676 (5)
N10.24265 (11)0.42475 (12)0.0671 (2)0.0382 (3)
O10.59814 (10)0.61106 (11)0.3536 (2)0.0507 (3)
O20.56797 (10)0.80092 (10)0.3658 (2)0.0548 (4)
C10.53650 (12)0.70252 (13)0.3221 (2)0.0368 (3)
C20.42188 (12)0.67765 (13)0.2324 (2)0.0338 (3)
C30.38678 (12)0.56431 (13)0.1906 (2)0.0349 (3)
C40.27962 (11)0.54398 (13)0.1120 (2)0.0349 (3)
C50.20654 (13)0.63421 (15)0.0749 (3)0.0405 (4)
C60.24265 (14)0.74709 (16)0.1160 (3)0.0440 (4)
C70.34984 (13)0.76929 (14)0.1933 (2)0.0392 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0293 (2)0.0436 (3)0.0385 (3)0.00505 (14)0.00343 (16)0.00286 (15)
O30.0291 (6)0.0571 (7)0.0564 (8)0.0071 (5)0.0050 (5)0.0035 (6)
O40.0554 (8)0.0737 (9)0.0343 (6)0.0298 (7)0.0024 (5)0.0032 (6)
O50.0659 (9)0.0969 (12)0.0340 (7)0.0440 (9)0.0018 (6)0.0011 (6)
N10.0327 (6)0.0409 (7)0.0375 (7)0.0037 (5)0.0027 (5)0.0006 (5)
O10.0344 (6)0.0395 (6)0.0692 (9)0.0026 (5)0.0035 (6)0.0007 (6)
O20.0398 (6)0.0382 (7)0.0809 (10)0.0047 (5)0.0053 (6)0.0070 (6)
C10.0347 (7)0.0352 (7)0.0384 (8)0.0010 (5)0.0058 (6)0.0011 (6)
C20.0325 (7)0.0349 (7)0.0323 (7)0.0002 (5)0.0054 (5)0.0008 (5)
C30.0314 (7)0.0344 (7)0.0363 (7)0.0022 (5)0.0037 (5)0.0013 (6)
C40.0311 (7)0.0392 (7)0.0321 (7)0.0002 (5)0.0041 (5)0.0005 (6)
C50.0303 (7)0.0479 (9)0.0405 (8)0.0046 (6)0.0041 (6)0.0013 (6)
C60.0407 (8)0.0461 (9)0.0428 (8)0.0122 (7)0.0064 (7)0.0017 (7)
C70.0438 (8)0.0358 (7)0.0363 (8)0.0048 (6)0.0070 (6)0.0031 (6)
Geometric parameters (Å, º) top
P1—O31.4930 (12)C1—C21.488 (2)
P1—O41.4932 (13)C2—C31.388 (2)
P1—O51.5590 (14)C2—C71.393 (2)
P1—H111.29 (2)C3—C41.380 (2)
O5—H120.92 (4)C3—H30.950 (19)
N1—C41.461 (2)C4—C51.389 (2)
N1—H80.95 (2)C5—C61.386 (2)
N1—H100.89 (3)C5—H51.02 (2)
N1—H90.90 (3)C6—C71.384 (2)
O1—C11.3091 (19)C6—H60.999 (19)
O1—H10.97 (4)C7—H71.00 (3)
O2—C11.2152 (19)
O3—P1—O4117.87 (8)C3—C2—C1120.47 (14)
O3—P1—O5106.36 (8)C7—C2—C1119.27 (14)
O4—P1—O5111.24 (8)C4—C3—C2119.02 (14)
O3—P1—H11106.3 (9)C4—C3—H3125.0 (11)
O4—P1—H11110.6 (9)C2—C3—H3115.9 (11)
O5—P1—H11103.4 (9)C3—C4—C5121.47 (14)
P1—O5—H12114 (2)C3—C4—N1119.07 (13)
C4—N1—H8110.7 (14)C5—C4—N1119.46 (13)
C4—N1—H10110.0 (15)C6—C5—C4118.96 (15)
H8—N1—H10109 (2)C6—C5—H5124.8 (13)
C4—N1—H9111.9 (18)C4—C5—H5116.2 (13)
H8—N1—H9109 (2)C7—C6—C5120.42 (15)
H10—N1—H9106 (2)C7—C6—H6116.9 (11)
C1—O1—H1101 (2)C5—C6—H6122.6 (11)
O2—C1—O1123.83 (15)C6—C7—C2119.86 (15)
O2—C1—C2121.22 (14)C6—C7—H7120.1 (15)
O1—C1—C2114.92 (13)C2—C7—H7120.0 (15)
C3—C2—C7120.26 (14)
O2—C1—C2—C71.6 (2)C2—C3—C4—N1179.71 (14)
O1—C1—C2—C7179.94 (14)C3—C4—C5—C60.7 (3)
O2—C1—C2—C3177.57 (16)N1—C4—C5—C6179.30 (15)
O1—C1—C2—C30.8 (2)C4—C5—C6—C70.2 (3)
C7—C2—C3—C40.6 (2)C5—C6—C7—C20.7 (3)
C1—C2—C3—C4178.47 (14)C3—C2—C7—C61.1 (2)
C2—C3—C4—C50.3 (2)C1—C2—C7—C6177.99 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.92 (4)1.64 (4)2.557 (2)176 (3)
O(1)—H(1)···O(3)ii0.97 (4)1.68 (4)2.5912 (18)154 (3)
N(1)—H(8)···O(4)iii0.95 (3)1.82 (3)2.7659 (18)173 (2)
N(1)—H(9)···O(2)iv0.91 (3)1.90 (4)2.787 (2)165 (2)
N(1)—H(10)···O(3)v0.88 (2)2.06 (3)2.8823 (19)154 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
(345K) top
Crystal data top
(C7H8NO2)+·(H2PO3)F(000) = 456
Mr = 219.13Dx = 1.510 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 24042 reflections
a = 13.0221 (11) Åθ = 3.4–30.0°
b = 11.5012 (8) ŵ = 0.28 mm1
c = 6.6489 (5) ÅT = 345 K
β = 104.614 (7)°Plate, brown
V = 963.59 (13) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Xcalibur-Saphire2
diffractometer
2815 independent reflections
Radiation source: fine-focus sealed tube2224 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 30.0°, θmin = 3.5°
Absorption correction: integration
Absorb, (DeTitta, 1985)
h = 1818
Tmin = 0.896, Tmax = 0.946k = 1616
24042 measured reflectionsl = 98
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0944P)2 + 0.0131P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.156(Δ/σ)max < 0.001
S = 1.12Δρmax = 0.49 e Å3
2815 reflectionsΔρmin = 0.26 e Å3
167 parameters
Crystal data top
(C7H8NO2)+·(H2PO3)V = 963.59 (13) Å3
Mr = 219.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.0221 (11) ŵ = 0.28 mm1
b = 11.5012 (8) ÅT = 345 K
c = 6.6489 (5) Å0.40 × 0.40 × 0.20 mm
β = 104.614 (7)°
Data collection top
Xcalibur-Saphire2
diffractometer
2815 independent reflections
Absorption correction: integration
Absorb, (DeTitta, 1985)
2224 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 0.946Rint = 0.049
24042 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.49 e Å3
2815 reflectionsΔρmin = 0.26 e Å3
167 parameters
Special details top

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
H10.160 (4)0.850 (3)0.281 (6)0.137 (15)*
H30.0607 (15)0.9954 (17)0.220 (3)0.041 (5)*
H50.371 (2)0.888 (2)0.113 (3)0.054 (6)*
H60.3047 (16)0.6846 (17)0.099 (3)0.042 (5)*
H70.123 (2)0.647 (2)0.157 (4)0.063 (7)*
H80.3064 (19)1.080 (2)0.266 (4)0.060 (6)*
H90.290 (2)1.101 (2)0.050 (4)0.071 (7)*
H100.207 (2)1.121 (2)0.230 (4)0.074 (8)*
H110.4476 (16)0.7730 (18)0.422 (3)0.049 (5)*
H120.508 (3)0.982 (3)0.310 (5)0.115 (11)*
P10.39507 (3)0.86539 (4)0.37837 (7)0.04097 (18)
O30.28998 (9)0.83314 (13)0.2400 (2)0.0532 (3)
O40.39668 (11)0.93119 (13)0.5722 (2)0.0614 (4)
O50.45540 (13)0.93216 (17)0.2401 (2)0.0733 (5)
N10.25777 (12)1.07453 (13)0.1750 (3)0.0414 (3)
O10.09802 (11)0.88877 (11)0.2449 (3)0.0548 (4)
O20.06828 (11)0.69896 (11)0.2047 (3)0.0592 (4)
C10.03659 (13)0.79736 (14)0.2158 (3)0.0397 (4)
C20.07796 (12)0.82181 (14)0.1908 (2)0.0366 (3)
C30.11340 (12)0.93524 (13)0.1968 (3)0.0377 (3)
C40.22054 (12)0.95509 (14)0.1677 (2)0.0373 (3)
C50.29333 (14)0.86462 (15)0.1326 (3)0.0439 (4)
C60.25680 (14)0.75218 (16)0.1287 (3)0.0476 (4)
C70.14988 (14)0.73004 (15)0.1585 (3)0.0424 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0317 (2)0.0462 (3)0.0462 (3)0.00520 (14)0.01193 (19)0.00585 (16)
O30.0320 (6)0.0617 (8)0.0650 (8)0.0080 (5)0.0105 (6)0.0085 (6)
O40.0602 (8)0.0785 (10)0.0553 (8)0.0317 (7)0.0329 (7)0.0195 (7)
O50.0708 (10)0.1053 (13)0.0534 (8)0.0471 (10)0.0334 (8)0.0250 (8)
N10.0362 (7)0.0436 (8)0.0468 (8)0.0037 (6)0.0150 (6)0.0015 (6)
O10.0375 (7)0.0421 (7)0.0880 (10)0.0023 (5)0.0219 (7)0.0021 (6)
O20.0426 (7)0.0411 (7)0.0931 (11)0.0056 (5)0.0160 (7)0.0048 (7)
C10.0377 (8)0.0379 (8)0.0446 (8)0.0007 (6)0.0122 (6)0.0020 (6)
C20.0356 (7)0.0370 (7)0.0387 (7)0.0008 (6)0.0124 (6)0.0012 (6)
C30.0340 (7)0.0365 (7)0.0445 (8)0.0021 (6)0.0131 (6)0.0004 (6)
C40.0340 (7)0.0412 (8)0.0386 (8)0.0001 (6)0.0127 (6)0.0006 (6)
C50.0334 (8)0.0522 (9)0.0471 (9)0.0054 (6)0.0121 (7)0.0038 (7)
C60.0443 (9)0.0491 (9)0.0506 (9)0.0135 (7)0.0145 (7)0.0088 (7)
C70.0472 (9)0.0385 (8)0.0440 (9)0.0053 (6)0.0162 (7)0.0056 (6)
Geometric parameters (Å, º) top
P1—O31.4904 (13)C1—C21.486 (2)
P1—O41.4898 (14)C2—C31.388 (2)
P1—O51.5543 (15)C2—C71.391 (2)
P1—H111.26 (2)C3—C41.378 (2)
O5—H120.93 (4)C3—H30.959 (19)
N1—C41.462 (2)C4—C51.387 (2)
N1—H80.98 (3)C5—C61.380 (3)
N1—H90.89 (3)C5—H51.02 (2)
N1—H100.86 (3)C6—C71.380 (2)
O1—C11.306 (2)C6—H60.985 (19)
O1—H10.90 (4)C7—H71.02 (2)
O2—C11.213 (2)
O3—P1—O4118.07 (8)C3—C2—C1120.44 (14)
O3—P1—O5106.28 (9)C7—C2—C1119.44 (14)
O4—P1—O5111.19 (8)C4—C3—C2118.94 (14)
O4—P1—H11110.0 (9)C4—C3—H3124.1 (11)
O3—P1—H11107.1 (9)C2—C3—H3116.9 (11)
O5—P1—H11103.1 (9)C3—C4—C5121.59 (15)
P1—O5—H12116 (2)C3—C4—N1118.92 (14)
C4—N1—H8110.5 (14)C5—C4—N1119.49 (14)
C4—N1—H9112.2 (16)C6—C5—C4118.80 (15)
C4—N1—H10112.1 (18)C6—C5—H5125.5 (13)
H8—N1—H9110 (2)C4—C5—H5115.7 (13)
H8—N1—H10104 (2)C7—C6—C5120.69 (15)
H10—N1—H9108 (2)C7—C6—H6116.6 (11)
C1—O1—H197 (3)C5—C6—H6122.7 (11)
O2—C1—O1123.72 (16)C6—C7—C2119.85 (16)
O2—C1—C2121.14 (14)C6—C7—H7120.8 (14)
O1—C1—C2115.12 (14)C2—C7—H7119.3 (14)
C3—C2—C7120.12 (15)
C7—C2—C1—O21.4 (3)C1—C2—C7—C6177.98 (16)
C7—C2—C1—O1179.87 (15)C2—C3—C4—C50.0 (2)
C3—C2—C1—O2177.80 (16)C2—C3—C4—N1179.76 (14)
C3—C2—C1—O10.7 (2)C6—C5—C4—C30.5 (3)
C7—C2—C3—C40.9 (2)C6—C5—C4—N1179.23 (16)
C1—C2—C3—C4178.33 (15)C2—C7—C6—C50.7 (3)
C3—C2—C7—C61.2 (2)C4—C5—C6—C70.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.92 (4)1.63 (4)2.555 (2)178 (3)
O(1)—H(1)···O(3)0.90 (5)1.79 (5)2.588 (2)146 (4)
N(1)—H(8)···O(4)ii0.98 (3)1.79 (3)2.764 (2)172 (2)
N(1)—H(10)···O(2)iii0.86 (2)1.96 (3)2.789 (2)161 (2)
N(1)—H(9)···O(3)iv0.89 (3)2.07 (3)2.887 (2)153 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+1; (iii) x, y+1/2, z+1/2; (iv) x, y+2, z.

Experimental details

(100K)(130K)(170K)(210K)
Crystal data
Chemical formula(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)
Mr219.13219.13219.13219.13
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)100130170210
a, b, c (Å)12.1405 (7), 12.4273 (9), 6.3851 (4)12.1342 (7), 12.3851 (6), 6.3821 (4)12.1740 (7), 12.3719 (6), 6.3995 (4)12.2065 (7), 12.3367 (7), 6.4102 (4)
β (°) 100.122 (5) 100.299 (5) 100.535 (5) 100.798 (5)
V3)948.35 (11)943.67 (9)947.62 (9)948.21 (10)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.290.290.290.29
Crystal size (mm)0.40 × 0.40 × 0.200.40 × 0.40 × 0.200.40 × 0.40 × 0.200.40 × 0.40 × 0.20
Data collection
DiffractometerXcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Absorption correctionIntegration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Tmin, Tmax0.908, 0.9380.908, 0.9380.890, 0.9420.887, 0.935
No. of measured, independent and
observed [I > 2σ(I)] reflections
78938, 2751, 2731 23422, 2732, 2424 23509, 2739, 2382 23560, 2747, 2346
Rint0.0320.0310.0310.032
(sin θ/λ)max1)0.7030.7030.7030.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.094, 1.08 0.034, 0.094, 1.06 0.035, 0.100, 1.04 0.037, 0.107, 1.08
No. of reflections2751273227392747
No. of parameters165167167167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.56, 0.320.44, 0.290.41, 0.270.39, 0.25


(235K)(255K)(293K)(320K)
Crystal data
Chemical formula(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)(C7H8NO2)+·(H2PO3)
Mr219.13219.13219.13219.13
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)235255293320
a, b, c (Å)12.2487 (9), 12.3265 (8), 6.4290 (5)13.0119 (14), 11.5643 (13), 6.6123 (7)13.036 (3), 11.538 (2), 6.6366 (13)13.0363 (8), 11.5204 (7), 6.6446 (5)
β (°) 100.981 (6) 104.433 (9) 104.73 (3) 104.826 (6)
V3)952.90 (12)963.57 (18)965.4 (4)964.69 (11)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.290.280.280.28
Crystal size (mm)0.40 × 0.40 × 0.200.40 × 0.40 × 0.200.40 × 0.40 × 0.200.40 × 0.40 × 0.20
Data collection
DiffractometerXcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Xcalibur-Saphire2
diffractometer
Absorption correctionIntegration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Integration
Absorb, (DeTitta, 1985)
Tmin, Tmax0.889, 0.9400.872, 0.9460.896, 0.9460.901, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections
23700, 2765, 2311 25199, 2814, 2432 26411, 2807, 2063 21224, 2816, 2243
Rint0.0330.0560.0410.035
(sin θ/λ)max1)0.7030.7030.7030.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.113, 1.10 0.050, 0.143, 1.08 0.037, 0.103, 0.99 0.047, 0.149, 1.14
No. of reflections2765281428072816
No. of parameters167167165167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.46, 0.270.39, 0.390.27, 0.340.53, 0.28


(345K)
Crystal data
Chemical formula(C7H8NO2)+·(H2PO3)
Mr219.13
Crystal system, space groupMonoclinic, P21/c
Temperature (K)345
a, b, c (Å)13.0221 (11), 11.5012 (8), 6.6489 (5)
β (°) 104.614 (7)
V3)963.59 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerXcalibur-Saphire2
diffractometer
Absorption correctionIntegration
Absorb, (DeTitta, 1985)
Tmin, Tmax0.896, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
24042, 2815, 2224
Rint0.049
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.156, 1.12
No. of reflections2815
No. of parameters167
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.49, 0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett,M. N & Johnson, C. K, 1996), WinGX publication routines (Farrugia, 1999).

Selected torsion angles (º) for (100K) top
O2—C1—C2—C74.22 (14)O2—C1—C2—C3175.79 (9)
O1—C1—C2—C7174.61 (9)O1—C1—C2—C35.38 (14)
Hydrogen-bond geometry (Å, º) for (100K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.979 (19)1.570 (19)2.5456 (11)173.4 (18)
O(1)—H(1)···O(3)ii0.901 (17)1.702 (18)2.5977 (11)172.3 (18)
N(1)—H(8)···O(4)iii0.895 (19)1.909 (19)2.7966 (12)170.9 (18)
N(1)—H(9)···O(2)iv0.850 (19)1.982 (19)2.8097 (12)164.5 (18)
N(1)—H(10)···O(3)v0.879 (18)1.961 (19)2.8096 (12)161.8 (17)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (130K) top
O2—C1—C2—C74.35 (17)O2—C1—C2—C3175.84 (11)
O1—C1—C2—C7174.68 (10)O1—C1—C2—C35.12 (16)
Hydrogen-bond geometry (Å, º) for (130K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i1.00 (2)1.54 (2)2.5386 (13)173.4 (18)
O(1)—H(1)···O(3)ii0.87 (3)1.73 (2)2.5919 (12)172.3 (18)
N(1)—H(8)···O(4)iii0.895 (19)1.883 (19)2.7916 (14)170.9 (18)
N(1)—H(9)···O(2)iv0.879 (19)1.948 (19)2.8037 (13)164.5 (18)
N(1)—H(10)···O(3)v0.879 (18)1.961 (19)2.8066 (13)159.9 (16)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (170K) top
O2—C1—C2—C74.23 (18)O2—C1—C2—C3176.04 (12)
O1—C1—C2—C7174.95 (11)O1—C1—C2—C34.78 (17)
Hydrogen-bond geometry (Å, º) for (170K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.98 (4)1.56 (4)2.5390 (14)173.4 (18)
O(1)—H(1)···O(3)ii0.85 (3)1.75 (2)2.5930 (13)172.3 (18)
N(1)—H(8)···O(4)iii0.931 (19)1.868 (19)2.7941 (14)173.0 (16)
N(1)—H(9)···O(2)iv0.878 (19)1.949 (19)2.8045 (14)164.5 (18)
N(1)—H(10)···O(3)v0.879 (18)1.981 (19)2.8116 (12)159.9 (17)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (210K) top
O2—C1—C2—C74.02 (19)O2—C1—C2—C3176.23 (12)
O1—C1—C2—C7175.19 (11)O1—C1—C2—C34.56 (18)
Hydrogen-bond geometry (Å, º) for (210K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.97 (4)1.57 (4)2.5367 (14)173.4 (18)
O(1)—H(1)···O(3)ii0.84 (3)1.76 (2)2.5900 (14)172.3 (18)
N(1)—H(8)···O(4)iii0.945 (18)1.853 (19)2.7901 (15)170.9 (18)
N(1)—H(9)···O(2)iv0.892 (19)1.934 (19)2.8035 (12)164.5 (18)
N(1)—H(10)···O(3)v0.901 (18)1.961 (19)2.8133 (15)159.5 (16)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (235K) top
O2—C1—C2—C73.9 (2)O2—C1—C2—C3176.46 (12)
O1—C1—C2—C7175.41 (12)O1—C1—C2—C34.28 (19)
Hydrogen-bond geometry (Å, º) for (235K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.94 (4)1.61 (4)2.5394 (15)173.4 (18)
O(1)—H(1)···O(3)ii0.81 (2)1.79 (2)2.5931 (14)172.3 (18)
N(1)—H(8)···O(4)iii0.956 (19)1.842 (19)2.7933 (15)172.9 (15)
N(1)—H(9)···O(2)iv0.892 (19)1.935 (19)2.8048 (15)164.5 (18)
N(1)—H(10)···O(3)v0.916 (18)1.961 (19)2.8204 (15)158.9 (16)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (255K) top
O2—C1—C2—C71.7 (2)O2—C1—C2—C3177.26 (15)
O1—C1—C2—C7179.98 (14)O1—C1—C2—C31.0 (2)
Hydrogen-bond geometry (Å, º) for (255K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.88 (4)1.69 (4)2.556 (2)173.4 (18)
O(1)—H(1)···O(3)ii1.01 (5)1.63 (5)2.5977 (11)160 (4)
N(1)—H(8)···O(4)iii0.96 (3)1.83 (3)2.7704 (18)170.9 (18)
N(1)—H(9)···O(2)iv0.93 (2)1.90 (3)2.7885 (19)159 (2)
N(1)—H(10)···O(3)v0.91 (2)2.00 (3)2.8585 (18)156 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (293K) top
O2—C1—C2—C3177.61 (14)O2—C1—C2—C71.4 (2)
O1—C1—C2—C31.0 (2)O1—C1—C2—C7179.99 (12)
Hydrogen-bond geometry (Å, º) for (293K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.86 (3)1.71 (3)2.5590 (19)168 (3)
O(1)—H(1)···O(3)ii0.85 (2)1.78 (3)2.5982 (16)161.1 (19)
N(1)—H(8)···O(4)iii0.917 (19)1.860 (19)2.7693 (17)170.9 (16)
N(1)—H(9)···O(2)iv0.96 (2)1.84 (3)2.7865 (17)166 (2)
N(1)—H(10)···O(3)v0.97 (3)1.94 (3)2.8740 (18)159 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (320K) top
O2—C1—C2—C71.6 (2)O2—C1—C2—C3177.57 (16)
O1—C1—C2—C7179.94 (14)O1—C1—C2—C30.8 (2)
Hydrogen-bond geometry (Å, º) for (320K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.92 (4)1.64 (4)2.557 (2)176 (3)
O(1)—H(1)···O(3)ii0.97 (4)1.68 (4)2.5912 (18)154 (3)
N(1)—H(8)···O(4)iii0.95 (3)1.82 (3)2.7659 (18)173 (2)
N(1)—H(9)···O(2)iv0.91 (3)1.90 (4)2.787 (2)164.5 (18)
N(1)—H(10)···O(3)v0.879 (18)2.06 (3)2.8823 (19)154 (2)
Symmetry codes: (i) x, y, z; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x+1, y1/2, z+1/2; (v) x, y+1/2, z+1/2.
Selected torsion angles (º) for (345K) top
C7—C2—C1—O21.4 (3)C3—C2—C1—O2177.80 (16)
C7—C2—C1—O1179.87 (15)C3—C2—C1—O10.7 (2)
Hydrogen-bond geometry (Å, º) for (345K) top
D—H···AD—HH···AD···AD—H···A
O(5)—H(12)···O(4)i0.92 (4)1.63 (4)2.555 (2)178 (3)
O(1)—H(1)···O(3)0.90 (5)1.79 (5)2.588 (2)146 (4)
N(1)—H(8)···O(4)ii0.98 (3)1.79 (3)2.764 (2)172 (2)
N(1)—H(10)···O(2)iii0.86 (2)1.96 (3)2.789 (2)161 (2)
N(1)—H(9)···O(3)iv0.89 (3)2.07 (3)2.887 (2)153 (2)
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+1; (iii) x, y+1/2, z+1/2; (iv) x, y+2, z.
 

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