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
CCDC references: 292332; 292333; 722685; 722686; 722687; 722688; 722689; 722691; 722692
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).
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 78938 reflections |
a = 12.1405 (7) Å | θ = 3.4–30.0° |
b = 12.4273 (9) Å | µ = 0.29 mm−1 |
c = 6.3851 (4) Å | T = 100 K |
β = 100.122 (5)° | Plate, brown |
V = 948.35 (11) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2751 independent reflections |
Radiation source: fine-focus sealed tube | 2731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→16 |
Tmin = 0.908, Tmax = 0.938 | k = 0→17 |
78938 measured reflections | l = 0→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.08 | Δρmax = 0.56 e Å−3 |
2751 reflections | Δρmin = −0.32 e Å−3 |
165 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 948.35 (11) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1405 (7) Å | µ = 0.29 mm−1 |
b = 12.4273 (9) Å | T = 100 K |
c = 6.3851 (4) Å | 0.40 × 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 = 0.938 | Rint = 0.032 |
78938 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.56 e Å−3 |
2751 reflections | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H3 | 0.4481 (14) | 0.4954 (14) | 0.200 (3) | 0.020 (4)* | |
H5 | 0.1146 (13) | 0.5682 (13) | 0.089 (3) | 0.017 (4)* | |
H6 | 0.1563 (14) | 0.7448 (14) | 0.207 (3) | 0.020 (4)* | |
H7 | 0.3429 (13) | 0.8000 (13) | 0.313 (2) | 0.013 (3)* | |
H8 | 0.1995 (15) | 0.4057 (15) | −0.048 (3) | 0.025 (4)* | |
H9 | 0.3077 (16) | 0.3710 (15) | 0.058 (3) | 0.026 (4)* | |
H10 | 0.2214 (14) | 0.3736 (14) | 0.171 (3) | 0.022 (4)* | |
H11 | 0.0350 (14) | 0.2349 (13) | 0.045 (3) | 0.019 (4)* | |
P1 | 0.08903 (2) | 0.148552 (19) | 0.00442 (4) | 0.01075 (9) | |
O3 | 0.19991 (6) | 0.18298 (6) | −0.05227 (12) | 0.01362 (15) | |
O4 | 0.09552 (7) | 0.07376 (6) | 0.19388 (12) | 0.01685 (16) | |
O5 | 0.01562 (7) | 0.09953 (6) | −0.20055 (12) | 0.01754 (17) | |
H12 | −0.0263 (15) | 0.0333 (15) | −0.187 (3) | 0.026* | |
N1 | 0.25015 (7) | 0.40729 (7) | 0.07221 (14) | 0.01168 (16) | |
O1 | 0.60643 (6) | 0.61538 (6) | 0.35793 (13) | 0.01649 (16) | |
O2 | 0.55142 (6) | 0.78693 (6) | 0.38997 (13) | 0.01573 (16) | |
C1 | 0.52995 (8) | 0.69219 (8) | 0.34391 (15) | 0.01197 (18) | |
C2 | 0.41256 (8) | 0.65463 (7) | 0.27064 (16) | 0.01128 (18) | |
C3 | 0.38907 (8) | 0.54785 (8) | 0.20498 (15) | 0.01163 (18) | |
C4 | 0.27782 (8) | 0.51850 (8) | 0.13834 (15) | 0.01088 (17) | |
C5 | 0.19020 (8) | 0.59120 (8) | 0.13855 (16) | 0.01305 (18) | |
C6 | 0.21458 (8) | 0.69674 (8) | 0.20500 (16) | 0.01388 (19) | |
C7 | 0.32573 (8) | 0.72896 (8) | 0.26893 (15) | 0.01301 (18) | |
H1 | 0.6753 (14) | 0.6396 (13) | 0.414 (3) | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.00984 (14) | 0.01082 (14) | 0.01095 (14) | −0.00121 (7) | 0.00005 (9) | −0.00014 (7) |
O3 | 0.0100 (3) | 0.0148 (3) | 0.0156 (3) | −0.0015 (2) | 0.0010 (2) | 0.0000 (3) |
O4 | 0.0198 (4) | 0.0174 (3) | 0.0116 (3) | −0.0077 (3) | −0.0020 (3) | 0.0022 (3) |
O5 | 0.0194 (4) | 0.0180 (4) | 0.0129 (3) | −0.0080 (3) | −0.0036 (3) | 0.0022 (3) |
N1 | 0.0111 (4) | 0.0104 (3) | 0.0128 (4) | −0.0008 (3) | 0.0001 (3) | −0.0006 (3) |
O1 | 0.0108 (3) | 0.0142 (3) | 0.0226 (4) | 0.0007 (3) | −0.0021 (3) | −0.0009 (3) |
O2 | 0.0133 (3) | 0.0136 (3) | 0.0200 (4) | −0.0024 (3) | 0.0021 (3) | −0.0029 (3) |
C1 | 0.0116 (4) | 0.0131 (4) | 0.0110 (4) | −0.0008 (3) | 0.0011 (3) | 0.0002 (3) |
C2 | 0.0104 (4) | 0.0115 (4) | 0.0115 (4) | −0.0012 (3) | 0.0005 (3) | −0.0001 (3) |
C3 | 0.0105 (4) | 0.0115 (4) | 0.0124 (4) | 0.0004 (3) | 0.0007 (3) | 0.0003 (3) |
C4 | 0.0112 (4) | 0.0103 (4) | 0.0107 (4) | −0.0010 (3) | 0.0007 (3) | −0.0002 (3) |
C5 | 0.0109 (4) | 0.0134 (4) | 0.0144 (4) | 0.0005 (3) | 0.0008 (3) | −0.0006 (3) |
C6 | 0.0111 (4) | 0.0142 (4) | 0.0158 (4) | 0.0021 (3) | 0.0008 (3) | −0.0017 (3) |
C7 | 0.0130 (4) | 0.0124 (4) | 0.0131 (4) | 0.0002 (3) | 0.0009 (3) | −0.0014 (3) |
Geometric parameters (Å, º) top
P1—O3 | 1.5157 (7) | C1—C2 | 1.4945 (13) |
P1—O4 | 1.5165 (8) | C2—C7 | 1.4002 (13) |
P1—O5 | 1.5711 (8) | C2—C3 | 1.4057 (13) |
P1—H11 | 1.307 (16) | C3—C4 | 1.3914 (13) |
O5—H12 | 0.979 (18) | C3—H3 | 0.973 (17) |
N1—C4 | 1.4668 (12) | C4—C5 | 1.3959 (13) |
N1—H8 | 0.894 (18) | C5—C6 | 1.3941 (14) |
N1—H9 | 0.849 (19) | C5—H5 | 0.960 (16) |
N1—H10 | 0.880 (18) | C6—C7 | 1.3980 (13) |
O1—C1 | 1.3236 (12) | C6—H6 | 0.928 (17) |
O1—H1 | 0.902 (17) | C7—H7 | 0.939 (16) |
O2—C1 | 1.2303 (12) | | |
| | | |
O3—P1—O4 | 116.08 (4) | C7—C2—C1 | 118.14 (8) |
O3—P1—O5 | 107.94 (4) | C3—C2—C1 | 121.36 (8) |
O4—P1—O5 | 111.67 (4) | C4—C3—C2 | 118.28 (9) |
O3—P1—H11 | 108.3 (7) | C4—C3—H3 | 119.7 (10) |
O4—P1—H11 | 107.6 (7) | C2—C3—H3 | 122.0 (10) |
O5—P1—H11 | 104.6 (7) | C3—C4—C5 | 121.94 (9) |
P1—O5—H12 | 118.7 (11) | C3—C4—N1 | 119.73 (8) |
C4—N1—H8 | 110.8 (12) | C5—C4—N1 | 118.30 (8) |
C4—N1—H9 | 112.3 (12) | C6—C5—C4 | 119.22 (9) |
H8—N1—H9 | 110.6 (16) | C6—C5—H5 | 121.3 (10) |
C4—N1—H10 | 110.0 (11) | C4—C5—H5 | 119.4 (10) |
H8—N1—H10 | 107.8 (15) | C5—C6—C7 | 120.05 (9) |
H9—N1—H10 | 105.2 (16) | C5—C6—H6 | 119.2 (10) |
C1—O1—H1 | 112.1 (11) | C7—C6—H6 | 120.7 (10) |
O2—C1—O1 | 123.87 (9) | C6—C7—C2 | 120.00 (9) |
O2—C1—C2 | 121.60 (9) | C6—C7—H7 | 120.6 (9) |
O1—C1—C2 | 114.52 (8) | C2—C7—H7 | 119.4 (9) |
C7—C2—C3 | 120.49 (9) | | |
| | | |
O2—C1—C2—C7 | −4.22 (14) | C2—C3—C4—N1 | −178.96 (8) |
O1—C1—C2—C7 | 174.61 (9) | C3—C4—C5—C6 | 0.77 (15) |
O2—C1—C2—C3 | 175.79 (9) | N1—C4—C5—C6 | 178.70 (9) |
O1—C1—C2—C3 | −5.38 (14) | C4—C5—C6—C7 | 0.47 (15) |
C7—C2—C3—C4 | 0.13 (14) | C5—C6—C7—C2 | −1.38 (15) |
C1—C2—C3—C4 | −179.88 (9) | C3—C2—C7—C6 | 1.08 (15) |
C2—C3—C4—C5 | −1.06 (14) | C1—C2—C7—C6 | −178.91 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.98 (2) | 1.57 (2) | 2.5456 (11) | 173 (2) |
O(1)—H(1)···O(3)ii | 0.90 (2) | 1.70 (2) | 2.5977 (11) | 172 (2) |
N(1)—H(8)···O(4)iii | 0.90 (2) | 1.91 (2) | 2.7966 (12) | 171 (2) |
N(1)—H(9)···O(2)iv | 0.85 (2) | 1.98 (2) | 2.8097 (12) | 165 (2) |
N(1)—H(10)···O(3)v | 0.88 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.542 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23422 reflections |
a = 12.1342 (7) Å | θ = 3.4–30.0° |
b = 12.3851 (6) Å | µ = 0.29 mm−1 |
c = 6.3821 (4) Å | T = 130 K |
β = 100.299 (5)° | Plate, brown |
V = 943.67 (9) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2732 independent reflections |
Radiation source: fine-focus sealed tube | 2424 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→17 |
Tmin = 0.908, Tmax = 0.938 | k = −17→17 |
23422 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.06 | Δρmax = 0.44 e Å−3 |
2732 reflections | Δρmin = −0.29 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 943.67 (9) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1342 (7) Å | µ = 0.29 mm−1 |
b = 12.3851 (6) Å | T = 130 K |
c = 6.3821 (4) Å | 0.40 × 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 = 0.938 | Rint = 0.031 |
23422 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.094 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.44 e Å−3 |
2732 reflections | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.672 (2) | 0.639 (2) | 0.414 (4) | 0.060 (7)* | |
H3 | 0.4505 (13) | 0.4953 (14) | 0.204 (3) | 0.023 (4)* | |
H5 | 0.1121 (13) | 0.5686 (13) | 0.086 (3) | 0.019 (4)* | |
H6 | 0.1555 (14) | 0.7464 (14) | 0.203 (3) | 0.020 (4)* | |
H7 | 0.3452 (13) | 0.8011 (12) | 0.314 (2) | 0.014 (3)* | |
H8 | 0.1985 (15) | 0.4067 (14) | −0.051 (3) | 0.028 (4)* | |
H9 | 0.3094 (15) | 0.3694 (15) | 0.058 (3) | 0.026 (4)* | |
H10 | 0.2210 (14) | 0.3724 (14) | 0.168 (3) | 0.024 (4)* | |
H12 | −0.025 (2) | 0.030 (2) | −0.185 (5) | 0.088 (9)* | |
H11 | 0.0352 (13) | 0.2343 (13) | 0.044 (3) | 0.019 (4)* | |
P1 | 0.08935 (2) | 0.14824 (2) | 0.00430 (4) | 0.01321 (10) | |
O3 | 0.19998 (7) | 0.18246 (7) | −0.05174 (13) | 0.01660 (18) | |
O4 | 0.09564 (8) | 0.07373 (7) | 0.19355 (14) | 0.02064 (19) | |
O5 | 0.01606 (8) | 0.09916 (7) | −0.20027 (14) | 0.0214 (2) | |
N1 | 0.25001 (8) | 0.40735 (7) | 0.07251 (16) | 0.01386 (19) | |
O1 | 0.60624 (7) | 0.61513 (7) | 0.35759 (15) | 0.01996 (19) | |
O2 | 0.55178 (7) | 0.78684 (7) | 0.38879 (14) | 0.01909 (19) | |
C1 | 0.53010 (9) | 0.69217 (9) | 0.34328 (18) | 0.0144 (2) | |
C2 | 0.41289 (9) | 0.65471 (9) | 0.26956 (18) | 0.0136 (2) | |
C3 | 0.38912 (9) | 0.54794 (9) | 0.20472 (17) | 0.0139 (2) | |
C4 | 0.27801 (9) | 0.51871 (8) | 0.13806 (17) | 0.0131 (2) | |
C5 | 0.19071 (9) | 0.59162 (9) | 0.13754 (18) | 0.0158 (2) | |
C6 | 0.21542 (10) | 0.69724 (9) | 0.20325 (19) | 0.0170 (2) | |
C7 | 0.32632 (9) | 0.72931 (9) | 0.26724 (18) | 0.0157 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01162 (15) | 0.01337 (15) | 0.01381 (16) | −0.00144 (9) | 0.00005 (10) | −0.00012 (9) |
O3 | 0.0121 (4) | 0.0181 (4) | 0.0189 (4) | −0.0015 (3) | 0.0010 (3) | 0.0002 (3) |
O4 | 0.0236 (4) | 0.0215 (4) | 0.0144 (4) | −0.0096 (3) | −0.0028 (3) | 0.0025 (3) |
O5 | 0.0235 (4) | 0.0224 (4) | 0.0154 (4) | −0.0100 (3) | −0.0044 (3) | 0.0032 (3) |
N1 | 0.0128 (4) | 0.0126 (4) | 0.0153 (5) | −0.0006 (3) | −0.0001 (3) | −0.0006 (3) |
O1 | 0.0123 (4) | 0.0176 (4) | 0.0276 (5) | 0.0004 (3) | −0.0029 (3) | −0.0008 (3) |
O2 | 0.0155 (4) | 0.0167 (4) | 0.0246 (4) | −0.0029 (3) | 0.0022 (3) | −0.0034 (3) |
C1 | 0.0134 (5) | 0.0158 (5) | 0.0135 (5) | −0.0013 (4) | 0.0015 (4) | 0.0001 (4) |
C2 | 0.0123 (5) | 0.0144 (5) | 0.0136 (5) | −0.0011 (4) | 0.0006 (4) | 0.0003 (4) |
C3 | 0.0122 (5) | 0.0144 (5) | 0.0146 (5) | 0.0004 (4) | 0.0009 (4) | 0.0003 (4) |
C4 | 0.0134 (5) | 0.0126 (4) | 0.0129 (5) | −0.0016 (4) | 0.0011 (4) | 0.0001 (4) |
C5 | 0.0130 (5) | 0.0166 (5) | 0.0171 (5) | 0.0005 (4) | 0.0008 (4) | −0.0007 (4) |
C6 | 0.0139 (5) | 0.0174 (5) | 0.0192 (5) | 0.0028 (4) | 0.0012 (4) | −0.0024 (4) |
C7 | 0.0158 (5) | 0.0147 (5) | 0.0158 (5) | 0.0001 (4) | 0.0010 (4) | −0.0017 (4) |
Geometric parameters (Å, º) top
P1—O3 | 1.5104 (9) | C1—C2 | 1.4900 (15) |
P1—O4 | 1.5110 (9) | C2—C7 | 1.3970 (15) |
P1—O5 | 1.5651 (9) | C2—C3 | 1.4001 (15) |
P1—H11 | 1.301 (16) | C3—C4 | 1.3873 (15) |
O5—H12 | 1.00 (3) | C3—H3 | 0.990 (17) |
N1—C4 | 1.4636 (14) | C4—C5 | 1.3915 (15) |
N1—H8 | 0.916 (18) | C5—C6 | 1.3899 (16) |
N1—H9 | 0.879 (18) | C5—H5 | 0.994 (16) |
N1—H10 | 0.870 (18) | C6—C7 | 1.3925 (15) |
O1—C1 | 1.3199 (14) | C6—H6 | 0.947 (17) |
O1—H1 | 0.86 (2) | C7—H7 | 0.952 (15) |
O2—C1 | 1.2252 (13) | | |
| | | |
O3—P1—O4 | 116.15 (5) | C7—C2—C1 | 118.09 (10) |
O3—P1—O5 | 107.94 (5) | C3—C2—C1 | 121.46 (10) |
O4—P1—O5 | 111.69 (5) | C4—C3—C2 | 118.34 (10) |
O3—P1—H11 | 108.5 (7) | C4—C3—H3 | 121.1 (10) |
O4—P1—H11 | 107.4 (7) | C2—C3—H3 | 120.5 (10) |
O5—P1—H11 | 104.4 (7) | C3—C4—C5 | 121.94 (10) |
P1—O5—H12 | 117.9 (17) | C3—C4—N1 | 119.79 (9) |
C4—N1—H8 | 110.0 (11) | C5—C4—N1 | 118.24 (9) |
C4—N1—H9 | 112.4 (11) | C6—C5—C4 | 119.14 (10) |
H8—N1—H9 | 110.5 (16) | C6—C5—H5 | 120.9 (9) |
C4—N1—H10 | 111.8 (11) | C4—C5—H5 | 119.9 (9) |
H8—N1—H10 | 107.4 (15) | C5—C6—C7 | 120.13 (10) |
H9—N1—H10 | 104.5 (15) | C5—C6—H6 | 118.6 (10) |
C1—O1—H1 | 111.0 (16) | C7—C6—H6 | 121.2 (10) |
O2—C1—O1 | 123.88 (10) | C6—C7—C2 | 119.99 (10) |
O2—C1—C2 | 121.68 (10) | C6—C7—H7 | 121.6 (9) |
O1—C1—C2 | 114.43 (9) | C2—C7—H7 | 118.4 (9) |
C7—C2—C3 | 120.44 (10) | | |
| | | |
O2—C1—C2—C7 | −4.35 (17) | C2—C3—C4—N1 | −179.01 (10) |
O1—C1—C2—C7 | 174.68 (10) | C3—C4—C5—C6 | 0.79 (17) |
O2—C1—C2—C3 | 175.84 (11) | N1—C4—C5—C6 | 178.74 (10) |
O1—C1—C2—C3 | −5.12 (16) | C4—C5—C6—C7 | 0.41 (18) |
C7—C2—C3—C4 | 0.19 (17) | C5—C6—C7—C2 | −1.29 (18) |
C1—C2—C3—C4 | 179.98 (10) | C3—C2—C7—C6 | 0.99 (17) |
C2—C3—C4—C5 | −1.09 (17) | C1—C2—C7—C6 | −178.82 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 1.00 (2) | 1.54 (2) | 2.5386 (13) | 173 (2) |
O(1)—H(1)···O(3)ii | 0.87 (3) | 1.73 (2) | 2.5919 (12) | 172 (2) |
N(1)—H(8)···O(4)iii | 0.90 (2) | 1.88 (2) | 2.7916 (14) | 171 (2) |
N(1)—H(9)···O(2)iv | 0.88 (2) | 1.95 (2) | 2.8037 (13) | 165 (2) |
N(1)—H(10)···O(3)v | 0.88 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.536 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23509 reflections |
a = 12.1740 (7) Å | θ = 3.4–30.0° |
b = 12.3719 (6) Å | µ = 0.29 mm−1 |
c = 6.3995 (4) Å | T = 170 K |
β = 100.535 (5)° | Plate, brown |
V = 947.62 (9) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2739 independent reflections |
Radiation source: fine-focus sealed tube | 2382 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→17 |
Tmin = 0.890, Tmax = 0.942 | k = −17→17 |
23509 measured reflections | l = −8→9 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.04 | Δρmax = 0.41 e Å−3 |
2739 reflections | Δρmin = −0.27 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 947.62 (9) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1740 (7) Å | µ = 0.29 mm−1 |
b = 12.3719 (6) Å | T = 170 K |
c = 6.3995 (4) Å | 0.40 × 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 = 0.942 | Rint = 0.031 |
23509 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.41 e Å−3 |
2739 reflections | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.670 (2) | 0.639 (2) | 0.411 (4) | 0.058 (7)* | |
H3 | 0.4511 (14) | 0.4950 (15) | 0.205 (3) | 0.029 (4)* | |
H5 | 0.1131 (14) | 0.5691 (14) | 0.082 (3) | 0.025 (4)* | |
H6 | 0.1565 (14) | 0.7486 (15) | 0.200 (3) | 0.026 (4)* | |
H7 | 0.3466 (13) | 0.8029 (13) | 0.309 (2) | 0.018 (4)* | |
H8 | 0.1977 (15) | 0.4078 (14) | −0.053 (3) | 0.029 (4)* | |
H9 | 0.3095 (16) | 0.3702 (15) | 0.059 (3) | 0.031 (5)* | |
H10 | 0.2207 (15) | 0.3736 (14) | 0.168 (3) | 0.026 (4)* | |
H12 | −0.025 (3) | 0.032 (3) | −0.184 (5) | 0.100 (10)* | |
H11 | 0.0361 (14) | 0.2328 (13) | 0.045 (3) | 0.024 (4)* | |
P1 | 0.08994 (2) | 0.14772 (2) | 0.00395 (5) | 0.01641 (10) | |
O3 | 0.20025 (7) | 0.18164 (7) | −0.05116 (14) | 0.02064 (19) | |
O4 | 0.09597 (8) | 0.07365 (8) | 0.19315 (14) | 0.0257 (2) | |
O5 | 0.01689 (8) | 0.09845 (8) | −0.20032 (15) | 0.0271 (2) | |
N1 | 0.24993 (9) | 0.40759 (8) | 0.07289 (17) | 0.0169 (2) | |
O1 | 0.60597 (8) | 0.61480 (8) | 0.35676 (16) | 0.0248 (2) | |
O2 | 0.55244 (7) | 0.78673 (7) | 0.38720 (16) | 0.0238 (2) | |
C1 | 0.53042 (10) | 0.69208 (9) | 0.34211 (19) | 0.0177 (2) | |
C2 | 0.41333 (10) | 0.65497 (9) | 0.26790 (19) | 0.0166 (2) | |
C3 | 0.38913 (9) | 0.54804 (9) | 0.20416 (18) | 0.0170 (2) | |
C4 | 0.27816 (9) | 0.51904 (9) | 0.13733 (18) | 0.0160 (2) | |
C5 | 0.19156 (10) | 0.59251 (10) | 0.1356 (2) | 0.0195 (2) | |
C6 | 0.21656 (10) | 0.69827 (10) | 0.2001 (2) | 0.0214 (2) | |
C7 | 0.32729 (10) | 0.73001 (10) | 0.26422 (19) | 0.0197 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01448 (16) | 0.01658 (16) | 0.01699 (17) | −0.00195 (9) | −0.00025 (11) | −0.00002 (10) |
O3 | 0.0150 (4) | 0.0221 (4) | 0.0238 (4) | −0.0019 (3) | 0.0009 (3) | 0.0002 (3) |
O4 | 0.0299 (5) | 0.0269 (4) | 0.0173 (4) | −0.0125 (4) | −0.0038 (3) | 0.0030 (3) |
O5 | 0.0297 (5) | 0.0284 (5) | 0.0191 (4) | −0.0136 (4) | −0.0063 (4) | 0.0042 (4) |
N1 | 0.0158 (5) | 0.0154 (4) | 0.0184 (5) | −0.0010 (3) | −0.0003 (4) | −0.0008 (3) |
O1 | 0.0153 (4) | 0.0214 (4) | 0.0346 (5) | 0.0004 (3) | −0.0040 (4) | −0.0010 (4) |
O2 | 0.0190 (4) | 0.0203 (4) | 0.0312 (5) | −0.0039 (3) | 0.0025 (4) | −0.0045 (3) |
C1 | 0.0166 (5) | 0.0192 (5) | 0.0167 (5) | −0.0016 (4) | 0.0017 (4) | 0.0001 (4) |
C2 | 0.0149 (5) | 0.0174 (5) | 0.0166 (5) | −0.0016 (4) | 0.0004 (4) | 0.0003 (4) |
C3 | 0.0152 (5) | 0.0172 (5) | 0.0178 (5) | 0.0009 (4) | 0.0009 (4) | 0.0004 (4) |
C4 | 0.0161 (5) | 0.0156 (5) | 0.0155 (5) | −0.0018 (4) | 0.0007 (4) | −0.0002 (4) |
C5 | 0.0157 (5) | 0.0205 (5) | 0.0211 (6) | 0.0006 (4) | 0.0005 (4) | −0.0010 (4) |
C6 | 0.0176 (5) | 0.0213 (5) | 0.0240 (6) | 0.0039 (4) | 0.0007 (4) | −0.0034 (4) |
C7 | 0.0202 (6) | 0.0176 (5) | 0.0202 (5) | 0.0004 (4) | 0.0008 (4) | −0.0025 (4) |
Geometric parameters (Å, º) top
P1—O3 | 1.5089 (9) | C1—C2 | 1.4902 (16) |
P1—O4 | 1.5095 (9) | C2—C7 | 1.3967 (16) |
P1—O5 | 1.5640 (9) | C2—C3 | 1.3998 (16) |
P1—H11 | 1.293 (16) | C3—C4 | 1.3876 (15) |
O5—H12 | 0.98 (3) | C3—H3 | 0.999 (18) |
N1—C4 | 1.4620 (14) | C4—C5 | 1.3905 (16) |
N1—H8 | 0.933 (18) | C5—C6 | 1.3890 (17) |
N1—H9 | 0.877 (19) | C5—H5 | 0.997 (17) |
N1—H10 | 0.865 (18) | C6—C7 | 1.3919 (17) |
O1—C1 | 1.3181 (14) | C6—H6 | 0.961 (18) |
O1—H1 | 0.85 (2) | C7—H7 | 0.962 (16) |
O2—C1 | 1.2240 (14) | | |
| | | |
O3—P1—O4 | 116.20 (5) | C7—C2—C1 | 118.13 (10) |
O3—P1—O5 | 107.90 (5) | C3—C2—C1 | 121.47 (10) |
O4—P1—O5 | 111.75 (5) | C4—C3—C2 | 118.38 (10) |
O3—P1—H11 | 109.1 (7) | C4—C3—H3 | 121.6 (10) |
O4—P1—H11 | 106.4 (7) | C2—C3—H3 | 120.0 (10) |
O5—P1—H11 | 104.9 (7) | C3—C4—C5 | 121.83 (10) |
P1—O5—H12 | 117.5 (19) | C3—C4—N1 | 119.74 (10) |
C4—N1—H8 | 109.3 (11) | C5—C4—N1 | 118.39 (10) |
C4—N1—H9 | 111.7 (12) | C6—C5—C4 | 119.27 (11) |
H8—N1—H9 | 111.1 (16) | C6—C5—H5 | 121.3 (10) |
C4—N1—H10 | 111.4 (11) | C4—C5—H5 | 119.4 (10) |
H8—N1—H10 | 107.8 (15) | C5—C6—C7 | 120.07 (11) |
H9—N1—H10 | 105.4 (16) | C5—C6—H6 | 119.0 (10) |
C1—O1—H1 | 110.9 (16) | C7—C6—H6 | 120.9 (10) |
O2—C1—O1 | 123.87 (11) | C6—C7—C2 | 120.03 (11) |
O2—C1—C2 | 121.69 (10) | C6—C7—H7 | 121.5 (9) |
O1—C1—C2 | 114.44 (10) | C2—C7—H7 | 118.4 (9) |
C7—C2—C3 | 120.40 (11) | | |
| | | |
O2—C1—C2—C7 | −4.23 (18) | C2—C3—C4—N1 | −179.04 (10) |
O1—C1—C2—C7 | 174.95 (11) | C3—C4—C5—C6 | 0.74 (18) |
O2—C1—C2—C3 | 176.04 (12) | N1—C4—C5—C6 | 178.79 (11) |
O1—C1—C2—C3 | −4.78 (17) | C4—C5—C6—C7 | 0.45 (19) |
C7—C2—C3—C4 | 0.14 (18) | C5—C6—C7—C2 | −1.31 (19) |
C1—C2—C3—C4 | 179.86 (11) | C3—C2—C7—C6 | 1.02 (19) |
C2—C3—C4—C5 | −1.02 (18) | C1—C2—C7—C6 | −178.71 (11) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.98 (4) | 1.56 (4) | 2.5390 (14) | 173 (2) |
O(1)—H(1)···O(3)ii | 0.85 (3) | 1.75 (2) | 2.5930 (13) | 172 (2) |
N(1)—H(8)···O(4)iii | 0.93 (2) | 1.87 (2) | 2.7941 (14) | 173 (2) |
N(1)—H(9)···O(2)iv | 0.88 (2) | 1.95 (2) | 2.8045 (14) | 165 (2) |
N(1)—H(10)···O(3)v | 0.88 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.535 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23560 reflections |
a = 12.2065 (7) Å | θ = 3.4–30.0° |
b = 12.3367 (7) Å | µ = 0.29 mm−1 |
c = 6.4102 (4) Å | T = 210 K |
β = 100.798 (5)° | Plate, brown |
V = 948.21 (10) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2747 independent reflections |
Radiation source: fine-focus sealed tube | 2346 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→17 |
Tmin = 0.887, Tmax = 0.935 | k = −17→17 |
23560 measured reflections | l = −9→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.08 | Δρmax = 0.39 e Å−3 |
2747 reflections | Δρmin = −0.25 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 948.21 (10) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2065 (7) Å | µ = 0.29 mm−1 |
b = 12.3367 (7) Å | T = 210 K |
c = 6.4102 (4) Å | 0.40 × 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 = 0.935 | Rint = 0.032 |
23560 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.39 e Å−3 |
2747 reflections | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.670 (2) | 0.637 (2) | 0.407 (4) | 0.063 (7)* | |
H3 | 0.4519 (14) | 0.4944 (14) | 0.203 (3) | 0.032 (4)* | |
H5 | 0.1134 (14) | 0.5699 (14) | 0.080 (3) | 0.030 (4)* | |
H6 | 0.1595 (14) | 0.7510 (15) | 0.193 (3) | 0.033 (4)* | |
H7 | 0.3467 (12) | 0.8037 (12) | 0.305 (2) | 0.020 (4)* | |
H8 | 0.1967 (14) | 0.4065 (14) | −0.055 (3) | 0.033 (4)* | |
H10 | 0.2190 (14) | 0.3735 (13) | 0.172 (3) | 0.028 (4)* | |
H9 | 0.3095 (16) | 0.3690 (15) | 0.060 (3) | 0.036 (5)* | |
H11 | 0.0359 (13) | 0.2317 (13) | 0.044 (3) | 0.026 (4)* | |
H12 | −0.022 (3) | 0.031 (3) | −0.185 (5) | 0.111 (11)* | |
P1 | 0.09072 (2) | 0.14711 (2) | 0.00333 (5) | 0.01986 (11) | |
O3 | 0.20068 (7) | 0.18070 (7) | −0.05062 (15) | 0.0248 (2) | |
O4 | 0.09641 (8) | 0.07358 (8) | 0.19270 (15) | 0.0310 (2) | |
O5 | 0.01826 (9) | 0.09736 (8) | −0.20040 (16) | 0.0334 (2) | |
N1 | 0.24964 (9) | 0.40797 (8) | 0.07301 (18) | 0.0206 (2) | |
O1 | 0.60564 (8) | 0.61442 (8) | 0.35609 (17) | 0.0300 (2) | |
O2 | 0.55321 (8) | 0.78672 (7) | 0.38543 (16) | 0.0287 (2) | |
C1 | 0.53074 (10) | 0.69214 (9) | 0.34069 (19) | 0.0211 (2) | |
C2 | 0.41380 (10) | 0.65549 (9) | 0.26596 (19) | 0.0200 (2) | |
C3 | 0.38913 (9) | 0.54832 (9) | 0.20321 (19) | 0.0202 (2) | |
C4 | 0.27839 (9) | 0.51969 (9) | 0.13620 (18) | 0.0190 (2) | |
C5 | 0.19246 (10) | 0.59376 (10) | 0.1330 (2) | 0.0236 (3) | |
C6 | 0.21798 (11) | 0.69967 (10) | 0.1957 (2) | 0.0261 (3) | |
C7 | 0.32846 (10) | 0.73101 (10) | 0.2606 (2) | 0.0234 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01713 (17) | 0.02028 (17) | 0.02058 (18) | −0.00251 (10) | −0.00055 (12) | 0.00010 (10) |
O3 | 0.0176 (4) | 0.0268 (4) | 0.0286 (5) | −0.0024 (3) | 0.0008 (3) | 0.0001 (4) |
O4 | 0.0355 (5) | 0.0329 (5) | 0.0206 (5) | −0.0151 (4) | −0.0047 (4) | 0.0035 (4) |
O5 | 0.0362 (5) | 0.0360 (5) | 0.0226 (5) | −0.0172 (4) | −0.0078 (4) | 0.0056 (4) |
N1 | 0.0187 (5) | 0.0190 (5) | 0.0226 (5) | −0.0008 (4) | −0.0002 (4) | −0.0009 (4) |
O1 | 0.0183 (4) | 0.0255 (4) | 0.0420 (6) | 0.0005 (3) | −0.0051 (4) | −0.0012 (4) |
O2 | 0.0228 (5) | 0.0242 (4) | 0.0380 (5) | −0.0049 (3) | 0.0029 (4) | −0.0056 (4) |
C1 | 0.0191 (5) | 0.0230 (5) | 0.0203 (6) | −0.0016 (4) | 0.0013 (4) | −0.0001 (4) |
C2 | 0.0177 (5) | 0.0206 (5) | 0.0204 (6) | −0.0012 (4) | 0.0001 (4) | 0.0007 (4) |
C3 | 0.0172 (5) | 0.0205 (5) | 0.0218 (6) | 0.0008 (4) | 0.0010 (4) | 0.0002 (4) |
C4 | 0.0186 (5) | 0.0189 (5) | 0.0183 (5) | −0.0013 (4) | 0.0005 (4) | −0.0004 (4) |
C5 | 0.0184 (5) | 0.0249 (6) | 0.0261 (6) | 0.0006 (4) | 0.0005 (4) | −0.0019 (4) |
C6 | 0.0209 (6) | 0.0256 (6) | 0.0301 (7) | 0.0055 (5) | 0.0004 (5) | −0.0047 (5) |
C7 | 0.0235 (6) | 0.0209 (5) | 0.0244 (6) | 0.0005 (4) | 0.0006 (5) | −0.0030 (4) |
Geometric parameters (Å, º) top
P1—O3 | 1.5056 (9) | C1—C2 | 1.4884 (16) |
P1—O4 | 1.5066 (10) | C2—C7 | 1.3931 (17) |
P1—O5 | 1.5594 (10) | C2—C3 | 1.3983 (16) |
P1—H11 | 1.292 (16) | C3—C4 | 1.3853 (16) |
O5—H12 | 0.97 (3) | C3—H3 | 1.015 (17) |
N1—C4 | 1.4606 (15) | C4—C5 | 1.3883 (16) |
N1—H8 | 0.945 (18) | C5—C6 | 1.3853 (18) |
N1—H9 | 0.892 (19) | C5—H5 | 1.006 (17) |
N1—H10 | 0.902 (18) | C6—C7 | 1.3895 (17) |
O1—C1 | 1.3157 (15) | C6—H6 | 0.953 (18) |
O1—H1 | 0.84 (2) | C7—H7 | 0.955 (15) |
O2—C1 | 1.2205 (14) | | |
| | | |
O3—P1—O4 | 116.25 (6) | C7—C2—C1 | 118.19 (10) |
O3—P1—O5 | 107.83 (6) | C3—C2—C1 | 121.44 (10) |
O4—P1—O5 | 111.78 (5) | C4—C3—C2 | 118.38 (11) |
O3—P1—H11 | 109.9 (7) | C4—C3—H3 | 121.7 (10) |
O4—P1—H11 | 105.8 (7) | C2—C3—H3 | 119.9 (10) |
O5—P1—H11 | 104.6 (7) | C3—C4—C5 | 121.83 (11) |
P1—O5—H12 | 118 (2) | C3—C4—N1 | 119.76 (10) |
C4—N1—H8 | 110.4 (11) | C5—C4—N1 | 118.39 (10) |
C4—N1—H9 | 112.1 (12) | C6—C5—C4 | 119.23 (11) |
C4—N1—H10 | 111.1 (10) | C6—C5—H5 | 121.6 (10) |
H8—N1—H9 | 110.2 (16) | C4—C5—H5 | 119.1 (10) |
H8—N1—H10 | 107.3 (15) | C5—C6—C7 | 120.15 (11) |
H9—N1—H10 | 105.6 (15) | C5—C6—H6 | 119.7 (11) |
C1—O1—H1 | 111.6 (17) | C7—C6—H6 | 120.2 (11) |
O2—C1—O1 | 123.82 (11) | C6—C7—C2 | 120.04 (11) |
O2—C1—C2 | 121.72 (11) | C6—C7—H7 | 120.7 (9) |
O1—C1—C2 | 114.45 (10) | C2—C7—H7 | 119.3 (9) |
C7—C2—C3 | 120.37 (11) | | |
| | | |
O2—C1—C2—C7 | −4.02 (19) | C2—C3—C4—N1 | −178.97 (11) |
O1—C1—C2—C7 | 175.19 (11) | C3—C4—C5—C6 | 0.89 (19) |
O2—C1—C2—C3 | 176.23 (12) | N1—C4—C5—C6 | 178.95 (12) |
O1—C1—C2—C3 | −4.56 (18) | C4—C5—C6—C7 | 0.1 (2) |
C7—C2—C3—C4 | −0.01 (18) | C5—C6—C7—C2 | −1.0 (2) |
C1—C2—C3—C4 | 179.74 (11) | C3—C2—C7—C6 | 1.0 (2) |
C2—C3—C4—C5 | −0.93 (18) | C1—C2—C7—C6 | −178.79 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.97 (4) | 1.57 (4) | 2.5367 (14) | 173 (2) |
O(1)—H(1)···O(3)ii | 0.84 (3) | 1.76 (2) | 2.5900 (14) | 172 (2) |
N(1)—H(8)···O(4)iii | 0.95 (2) | 1.85 (2) | 2.7901 (15) | 171 (2) |
N(1)—H(9)···O(2)iv | 0.89 (2) | 1.93 (2) | 2.8035 (12) | 165 (2) |
N(1)—H(10)···O(3)v | 0.90 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.527 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23700 reflections |
a = 12.2487 (9) Å | θ = 3.4–30.0° |
b = 12.3265 (8) Å | µ = 0.29 mm−1 |
c = 6.4290 (5) Å | T = 235 K |
β = 100.981 (6)° | Plate, brown |
V = 952.90 (12) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2765 independent reflections |
Radiation source: fine-focus sealed tube | 2311 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 30.0°, θmin = 3.4° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→17 |
Tmin = 0.889, Tmax = 0.940 | k = −17→17 |
23700 measured reflections | l = −9→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.10 | Δρmax = 0.46 e Å−3 |
2765 reflections | Δρmin = −0.27 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 952.90 (12) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2487 (9) Å | µ = 0.29 mm−1 |
b = 12.3265 (8) Å | T = 235 K |
c = 6.4290 (5) Å | 0.40 × 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 = 0.940 | Rint = 0.033 |
23700 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.46 e Å−3 |
2765 reflections | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.6667 (19) | 0.6370 (17) | 0.403 (4) | 0.056 (6)* | |
H3 | 0.4516 (14) | 0.4936 (15) | 0.204 (3) | 0.043 (5)* | |
H5 | 0.1131 (14) | 0.5692 (15) | 0.074 (3) | 0.038 (4)* | |
H6 | 0.1611 (14) | 0.7524 (15) | 0.195 (3) | 0.037 (4)* | |
H7 | 0.3467 (12) | 0.8045 (12) | 0.303 (2) | 0.021 (4)* | |
H8 | 0.1973 (14) | 0.4082 (13) | −0.058 (3) | 0.034 (4)* | |
H9 | 0.3083 (16) | 0.3676 (14) | 0.061 (3) | 0.039 (5)* | |
H10 | 0.2181 (13) | 0.3735 (13) | 0.173 (3) | 0.030 (4)* | |
H12 | −0.020 (3) | 0.033 (3) | −0.184 (5) | 0.120 (11)* | |
H11 | 0.0360 (12) | 0.2313 (12) | 0.041 (2) | 0.026 (4)* | |
P1 | 0.09136 (3) | 0.14663 (2) | 0.00270 (5) | 0.02236 (12) | |
O3 | 0.20098 (7) | 0.18003 (7) | −0.05017 (15) | 0.0276 (2) | |
O4 | 0.09670 (9) | 0.07350 (8) | 0.19221 (15) | 0.0346 (2) | |
O5 | 0.01936 (9) | 0.09658 (9) | −0.20068 (16) | 0.0377 (3) | |
N1 | 0.24952 (9) | 0.40822 (8) | 0.07301 (18) | 0.0230 (2) | |
O1 | 0.60532 (8) | 0.61408 (8) | 0.35557 (18) | 0.0335 (2) | |
O2 | 0.55380 (8) | 0.78678 (7) | 0.38396 (17) | 0.0321 (2) | |
C1 | 0.53100 (10) | 0.69215 (9) | 0.3395 (2) | 0.0237 (2) | |
C2 | 0.41422 (10) | 0.65590 (9) | 0.2642 (2) | 0.0223 (2) | |
C3 | 0.38899 (10) | 0.54859 (10) | 0.20249 (19) | 0.0224 (2) | |
C4 | 0.27857 (10) | 0.52009 (9) | 0.13543 (19) | 0.0212 (2) | |
C5 | 0.19305 (10) | 0.59481 (10) | 0.1307 (2) | 0.0262 (3) | |
C6 | 0.21920 (11) | 0.70094 (11) | 0.1925 (2) | 0.0293 (3) | |
C7 | 0.32925 (11) | 0.73192 (10) | 0.2573 (2) | 0.0264 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.01911 (18) | 0.02290 (18) | 0.02319 (19) | −0.00300 (10) | −0.00071 (12) | 0.00020 (11) |
O3 | 0.0195 (4) | 0.0299 (4) | 0.0319 (5) | −0.0027 (3) | 0.0011 (4) | 0.0002 (4) |
O4 | 0.0393 (6) | 0.0368 (5) | 0.0232 (5) | −0.0171 (4) | −0.0051 (4) | 0.0037 (4) |
O5 | 0.0410 (6) | 0.0414 (6) | 0.0248 (5) | −0.0205 (5) | −0.0087 (4) | 0.0062 (4) |
N1 | 0.0206 (5) | 0.0214 (5) | 0.0251 (6) | −0.0009 (4) | −0.0009 (4) | −0.0009 (4) |
O1 | 0.0205 (5) | 0.0285 (5) | 0.0468 (6) | 0.0006 (4) | −0.0061 (4) | −0.0015 (4) |
O2 | 0.0248 (5) | 0.0267 (4) | 0.0434 (6) | −0.0054 (4) | 0.0031 (4) | −0.0061 (4) |
C1 | 0.0216 (5) | 0.0250 (6) | 0.0232 (6) | −0.0021 (4) | 0.0011 (4) | 0.0000 (4) |
C2 | 0.0197 (5) | 0.0230 (5) | 0.0229 (6) | −0.0014 (4) | 0.0005 (4) | 0.0000 (4) |
C3 | 0.0193 (5) | 0.0227 (5) | 0.0238 (6) | 0.0009 (4) | 0.0008 (4) | 0.0001 (4) |
C4 | 0.0203 (5) | 0.0215 (5) | 0.0204 (5) | −0.0016 (4) | 0.0002 (4) | −0.0005 (4) |
C5 | 0.0204 (6) | 0.0277 (6) | 0.0288 (7) | 0.0010 (4) | 0.0001 (5) | −0.0028 (5) |
C6 | 0.0238 (6) | 0.0285 (6) | 0.0335 (7) | 0.0064 (5) | −0.0001 (5) | −0.0051 (5) |
C7 | 0.0265 (6) | 0.0231 (6) | 0.0277 (6) | 0.0011 (5) | 0.0004 (5) | −0.0037 (5) |
Geometric parameters (Å, º) top
P1—O3 | 1.5040 (10) | C1—C2 | 1.4887 (17) |
P1—O4 | 1.5069 (10) | C2—C7 | 1.3949 (17) |
P1—O5 | 1.5585 (10) | C2—C3 | 1.3985 (16) |
P1—H11 | 1.294 (15) | C3—C4 | 1.3843 (16) |
O5—H12 | 0.94 (3) | C3—H3 | 1.022 (18) |
N1—C4 | 1.4610 (15) | C4—C5 | 1.3908 (16) |
N1—H8 | 0.954 (17) | C5—C6 | 1.3868 (18) |
N1—H9 | 0.893 (19) | C5—H5 | 1.028 (17) |
N1—H10 | 0.918 (17) | C6—C7 | 1.3866 (18) |
O1—C1 | 1.3152 (15) | C6—H6 | 0.956 (18) |
O1—H1 | 0.81 (2) | C7—H7 | 0.954 (14) |
O2—C1 | 1.2205 (14) | | |
| | | |
O3—P1—O4 | 116.32 (6) | C7—C2—C1 | 118.27 (11) |
O3—P1—O5 | 107.80 (6) | C3—C2—C1 | 121.53 (11) |
O4—P1—O5 | 111.84 (5) | C4—C3—C2 | 118.58 (11) |
O3—P1—H11 | 110.2 (7) | C4—C3—H3 | 121.4 (10) |
O4—P1—H11 | 105.8 (7) | C2—C3—H3 | 120.0 (10) |
O5—P1—H11 | 104.3 (7) | C3—C4—C5 | 121.72 (11) |
P1—O5—H12 | 117 (2) | C3—C4—N1 | 119.83 (10) |
C4—N1—H8 | 109.3 (10) | C5—C4—N1 | 118.43 (10) |
C4—N1—H9 | 113.3 (11) | C6—C5—C4 | 119.12 (11) |
H8—N1—H9 | 109.8 (15) | C6—C5—H5 | 122.9 (10) |
C4—N1—H10 | 111.1 (10) | C4—C5—H5 | 117.9 (10) |
H8—N1—H10 | 108.6 (14) | C7—C6—C5 | 120.27 (12) |
H9—N1—H10 | 104.7 (15) | C7—C6—H6 | 119.7 (10) |
C1—O1—H1 | 110.8 (15) | C5—C6—H6 | 120.0 (11) |
O2—C1—O1 | 123.83 (12) | C6—C7—C2 | 120.09 (12) |
O2—C1—C2 | 121.72 (11) | C6—C7—H7 | 119.9 (9) |
O1—C1—C2 | 114.44 (10) | C2—C7—H7 | 119.9 (9) |
C7—C2—C3 | 120.20 (11) | | |
| | | |
O2—C1—C2—C7 | −3.9 (2) | C2—C3—C4—N1 | −179.08 (11) |
O1—C1—C2—C7 | 175.41 (12) | C3—C4—C5—C6 | 0.78 (19) |
O2—C1—C2—C3 | 176.46 (12) | N1—C4—C5—C6 | 179.07 (12) |
O1—C1—C2—C3 | −4.28 (19) | C4—C5—C6—C7 | 0.2 (2) |
C7—C2—C3—C4 | −0.13 (19) | C5—C6—C7—C2 | −1.1 (2) |
C1—C2—C3—C4 | 179.56 (11) | C3—C2—C7—C6 | 1.1 (2) |
C2—C3—C4—C5 | −0.81 (19) | C1—C2—C7—C6 | −178.62 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.94 (4) | 1.61 (4) | 2.5394 (15) | 173 (2) |
O(1)—H(1)···O(3)ii | 0.81 (2) | 1.79 (2) | 2.5931 (14) | 172 (2) |
N(1)—H(8)···O(4)iii | 0.96 (2) | 1.84 (2) | 2.7933 (15) | 173 (2) |
N(1)—H(9)···O(2)iv | 0.89 (2) | 1.94 (2) | 2.8048 (15) | 165 (2) |
N(1)—H(10)···O(3)v | 0.92 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.511 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25199 reflections |
a = 13.0119 (14) Å | θ = 3.4–30.0° |
b = 11.5643 (13) Å | µ = 0.28 mm−1 |
c = 6.6123 (7) Å | T = 255 K |
β = 104.433 (9)° | Plate, brown |
V = 963.57 (18) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2814 independent reflections |
Radiation source: fine-focus sealed tube | 2432 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 30.0°, θmin = 3.5° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −18→18 |
Tmin = 0.872, Tmax = 0.946 | k = −15→16 |
25199 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.08 | Δρmax = 0.39 e Å−3 |
2814 reflections | Δρmin = −0.39 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 963.57 (18) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0119 (14) Å | µ = 0.28 mm−1 |
b = 11.5643 (13) Å | T = 255 K |
c = 6.6123 (7) Å | 0.40 × 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 = 0.946 | Rint = 0.056 |
25199 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.39 e Å−3 |
2814 reflections | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.673 (4) | 0.642 (4) | 0.403 (7) | 0.142 (18)* | |
H3 | 0.4395 (18) | 0.500 (2) | 0.220 (4) | 0.046 (6)* | |
H5 | 0.1316 (19) | 0.613 (2) | 0.020 (3) | 0.039 (5)* | |
H6 | 0.1903 (16) | 0.8072 (18) | 0.101 (3) | 0.034 (5)* | |
H7 | 0.373 (2) | 0.845 (2) | 0.232 (4) | 0.056 (7)* | |
H8 | 0.194 (2) | 0.415 (2) | −0.066 (4) | 0.054 (7)* | |
H9 | 0.296 (2) | 0.3679 (19) | 0.067 (4) | 0.049 (7)* | |
H10 | 0.2128 (18) | 0.3940 (19) | 0.166 (4) | 0.040 (5)* | |
H12 | −0.011 (3) | 0.029 (3) | −0.199 (5) | 0.093 (11)* | |
H11 | 0.0532 (17) | 0.2299 (19) | −0.019 (3) | 0.039 (5)* | |
P1 | 0.10388 (3) | 0.13609 (4) | −0.01814 (6) | 0.03022 (15) | |
O3 | 0.20965 (8) | 0.16855 (11) | −0.05309 (19) | 0.0370 (3) | |
O4 | 0.10332 (11) | 0.06916 (13) | 0.17567 (18) | 0.0455 (3) | |
O5 | 0.04247 (12) | 0.06999 (15) | −0.21812 (19) | 0.0535 (4) | |
N1 | 0.24362 (10) | 0.42220 (12) | 0.0667 (2) | 0.0301 (3) | |
O1 | 0.59874 (9) | 0.61054 (11) | 0.3554 (2) | 0.0404 (3) | |
O2 | 0.56657 (10) | 0.79956 (11) | 0.3718 (2) | 0.0434 (3) | |
C1 | 0.53603 (11) | 0.70140 (13) | 0.3259 (2) | 0.0297 (3) | |
C2 | 0.42134 (11) | 0.67560 (13) | 0.2358 (2) | 0.0274 (3) | |
C3 | 0.38725 (11) | 0.56238 (13) | 0.1924 (2) | 0.0282 (3) | |
C4 | 0.27973 (11) | 0.54135 (13) | 0.1130 (2) | 0.0279 (3) | |
C5 | 0.20578 (12) | 0.63065 (14) | 0.0785 (3) | 0.0324 (3) | |
C6 | 0.24104 (13) | 0.74361 (15) | 0.1209 (3) | 0.0351 (3) | |
C7 | 0.34869 (13) | 0.76646 (14) | 0.1989 (2) | 0.0319 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0230 (2) | 0.0361 (2) | 0.0296 (2) | −0.00443 (13) | 0.00286 (15) | 0.00206 (13) |
O3 | 0.0234 (5) | 0.0450 (6) | 0.0406 (6) | −0.0062 (4) | 0.0041 (4) | 0.0019 (5) |
O4 | 0.0444 (7) | 0.0592 (8) | 0.0273 (6) | −0.0250 (6) | −0.0017 (5) | 0.0029 (5) |
O5 | 0.0502 (8) | 0.0772 (11) | 0.0284 (6) | −0.0348 (7) | 0.0010 (5) | 0.0021 (6) |
N1 | 0.0249 (6) | 0.0333 (6) | 0.0299 (6) | −0.0032 (5) | 0.0026 (5) | 0.0005 (5) |
O1 | 0.0270 (5) | 0.0329 (6) | 0.0543 (7) | 0.0018 (4) | −0.0033 (5) | −0.0010 (5) |
O2 | 0.0309 (6) | 0.0327 (6) | 0.0630 (8) | −0.0039 (5) | 0.0049 (5) | −0.0062 (5) |
C1 | 0.0272 (6) | 0.0306 (7) | 0.0300 (7) | −0.0005 (5) | 0.0044 (5) | 0.0007 (5) |
C2 | 0.0258 (6) | 0.0294 (7) | 0.0256 (6) | 0.0003 (5) | 0.0039 (5) | 0.0001 (5) |
C3 | 0.0245 (6) | 0.0294 (7) | 0.0288 (6) | 0.0009 (5) | 0.0032 (5) | 0.0016 (5) |
C4 | 0.0251 (6) | 0.0322 (7) | 0.0248 (6) | −0.0003 (5) | 0.0031 (5) | 0.0008 (5) |
C5 | 0.0239 (7) | 0.0393 (8) | 0.0321 (7) | 0.0032 (5) | 0.0035 (5) | −0.0012 (6) |
C6 | 0.0316 (7) | 0.0376 (8) | 0.0338 (7) | 0.0095 (6) | 0.0041 (6) | −0.0029 (6) |
C7 | 0.0338 (7) | 0.0311 (7) | 0.0296 (7) | 0.0033 (6) | 0.0056 (5) | −0.0031 (5) |
Geometric parameters (Å, º) top
P1—O3 | 1.4990 (11) | C1—C2 | 1.493 (2) |
P1—O4 | 1.4987 (13) | C2—C3 | 1.389 (2) |
P1—O5 | 1.5635 (14) | C2—C7 | 1.394 (2) |
P1—H11 | 1.27 (2) | C3—C4 | 1.388 (2) |
O5—H12 | 0.88 (4) | C3—H3 | 0.97 (2) |
N1—C4 | 1.4633 (19) | C4—C5 | 1.391 (2) |
N1—H8 | 0.95 (3) | C5—C6 | 1.390 (2) |
N1—H9 | 0.93 (3) | C5—H5 | 0.97 (2) |
N1—H10 | 0.91 (2) | C6—C7 | 1.392 (2) |
O1—C1 | 1.3147 (19) | C6—H6 | 0.97 (2) |
O1—H1 | 1.00 (5) | C7—H7 | 0.96 (3) |
O2—C1 | 1.2159 (19) | | |
| | | |
O4—P1—O3 | 117.48 (7) | C3—C2—C1 | 120.45 (13) |
O4—P1—O5 | 111.12 (7) | C7—C2—C1 | 119.09 (13) |
O3—P1—O5 | 106.70 (8) | C4—C3—C2 | 118.89 (13) |
O4—P1—H11 | 109.5 (9) | C4—C3—H3 | 122.2 (14) |
O3—P1—H11 | 106.3 (10) | C2—C3—H3 | 118.9 (14) |
O5—P1—H11 | 104.9 (9) | C3—C4—C5 | 121.52 (14) |
P1—O5—H12 | 113 (2) | C3—C4—N1 | 119.02 (13) |
C4—N1—H8 | 112.8 (16) | C5—C4—N1 | 119.46 (13) |
C4—N1—H9 | 116.0 (15) | C6—C5—C4 | 118.99 (14) |
H8—N1—H9 | 105 (2) | C6—C5—H5 | 121.9 (14) |
C4—N1—H10 | 111.3 (14) | C4—C5—H5 | 119.0 (14) |
H8—N1—H10 | 108 (2) | C5—C6—C7 | 120.29 (14) |
H9—N1—H10 | 102 (2) | C5—C6—H6 | 120.2 (12) |
C1—O1—H1 | 106 (3) | C7—C6—H6 | 119.5 (12) |
O2—C1—O1 | 123.84 (14) | C6—C7—C2 | 119.84 (15) |
O2—C1—C2 | 121.22 (14) | C6—C7—H7 | 120.1 (16) |
O1—C1—C2 | 114.92 (13) | C2—C7—H7 | 120.0 (16) |
C3—C2—C7 | 120.45 (14) | | |
| | | |
O2—C1—C2—C7 | 1.7 (2) | C2—C3—C4—N1 | 179.85 (13) |
O1—C1—C2—C7 | 179.98 (14) | C3—C4—C5—C6 | 1.3 (2) |
O2—C1—C2—C3 | −177.26 (15) | N1—C4—C5—C6 | −179.32 (14) |
O1—C1—C2—C3 | 1.0 (2) | C4—C5—C6—C7 | −0.7 (2) |
C7—C2—C3—C4 | −0.4 (2) | C5—C6—C7—C2 | −0.4 (2) |
C1—C2—C3—C4 | 178.60 (13) | C3—C2—C7—C6 | 0.9 (2) |
C2—C3—C4—C5 | −0.8 (2) | C1—C2—C7—C6 | −178.07 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.88 (4) | 1.69 (4) | 2.556 (2) | 173 (2) |
O(1)—H(1)···O(3)ii | 1.01 (5) | 1.63 (5) | 2.5977 (11) | 160 (4) |
N(1)—H(8)···O(4)iii | 0.96 (3) | 1.83 (3) | 2.7704 (18) | 171 (2) |
N(1)—H(9)···O(2)iv | 0.93 (2) | 1.90 (3) | 2.7885 (19) | 159 (2) |
N(1)—H(10)···O(3)v | 0.91 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.508 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 26411 reflections |
a = 13.036 (3) Å | θ = 4.8–30.0° |
b = 11.538 (2) Å | µ = 0.28 mm−1 |
c = 6.6366 (13) Å | T = 293 K |
β = 104.73 (3)° | Plate, brown |
V = 965.4 (4) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2807 independent reflections |
Radiation source: fine-focus sealed tube | 2063 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 30.0°, θmin = 4.8° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −17→18 |
Tmin = 0.896, Tmax = 0.946 | k = −16→0 |
26411 measured reflections | l = −9→0 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 0.99 | Δρmax = 0.27 e Å−3 |
2807 reflections | Δρmin = −0.34 e Å−3 |
165 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 965.4 (4) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.036 (3) Å | µ = 0.28 mm−1 |
b = 11.538 (2) Å | T = 293 K |
c = 6.6366 (13) Å | 0.40 × 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 = 0.946 | Rint = 0.041 |
26411 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.27 e Å−3 |
2807 reflections | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H5 | 0.1278 (14) | 0.6071 (16) | 0.008 (2) | 0.050 (5)* | |
H6 | 0.1955 (12) | 0.8086 (13) | 0.104 (2) | 0.035 (4)* | |
H3 | 0.4417 (12) | 0.5040 (14) | 0.225 (2) | 0.044 (4)* | |
H11 | 0.0527 (12) | 0.2268 (14) | −0.017 (2) | 0.048 (4)* | |
H7 | 0.3723 (14) | 0.8526 (16) | 0.211 (3) | 0.058 (5)* | |
H8 | 0.1949 (14) | 0.4182 (14) | −0.060 (3) | 0.049 (4)* | |
H10 | 0.2138 (19) | 0.3977 (18) | 0.181 (3) | 0.082 (6)* | |
H9 | 0.3012 (19) | 0.3710 (18) | 0.079 (3) | 0.080 (7)* | |
P1 | 0.10445 (3) | 0.13531 (3) | −0.01752 (6) | 0.03572 (13) | |
O3 | 0.20964 (7) | 0.16772 (9) | −0.05157 (17) | 0.0454 (3) | |
O4 | 0.10345 (9) | 0.06901 (10) | 0.17558 (15) | 0.0533 (3) | |
O5 | 0.04365 (10) | 0.06885 (13) | −0.21676 (16) | 0.0639 (4) | |
H12 | 0.001 (2) | 0.016 (2) | −0.196 (4) | 0.096* | |
N1 | 0.24297 (9) | 0.42377 (10) | 0.0673 (2) | 0.0358 (3) | |
O1 | 0.59823 (8) | 0.61087 (9) | 0.35419 (18) | 0.0478 (3) | |
O2 | 0.56758 (8) | 0.80059 (8) | 0.36805 (19) | 0.0511 (3) | |
C1 | 0.53616 (10) | 0.70225 (11) | 0.3236 (2) | 0.0345 (3) | |
C2 | 0.42153 (10) | 0.67703 (11) | 0.2333 (2) | 0.0320 (3) | |
C3 | 0.38699 (10) | 0.56395 (11) | 0.1909 (2) | 0.0331 (3) | |
C4 | 0.27981 (10) | 0.54327 (11) | 0.11227 (19) | 0.0324 (3) | |
C5 | 0.20668 (11) | 0.63335 (12) | 0.0767 (2) | 0.0387 (3) | |
C6 | 0.24259 (11) | 0.74588 (13) | 0.1175 (2) | 0.0408 (3) | |
C7 | 0.34918 (11) | 0.76837 (12) | 0.1949 (2) | 0.0373 (3) | |
H1 | 0.6608 (16) | 0.6387 (15) | 0.395 (3) | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.02716 (18) | 0.0416 (2) | 0.0360 (2) | −0.00476 (13) | 0.00350 (13) | 0.00284 (14) |
O3 | 0.0274 (5) | 0.0541 (6) | 0.0519 (7) | −0.0065 (4) | 0.0049 (4) | 0.0041 (5) |
O4 | 0.0521 (6) | 0.0694 (8) | 0.0317 (5) | −0.0281 (5) | −0.0018 (4) | 0.0040 (5) |
O5 | 0.0619 (8) | 0.0905 (10) | 0.0334 (6) | −0.0415 (7) | 0.0016 (5) | 0.0026 (5) |
N1 | 0.0299 (6) | 0.0391 (6) | 0.0349 (7) | −0.0036 (5) | 0.0019 (5) | −0.0003 (5) |
O1 | 0.0315 (5) | 0.0376 (6) | 0.0656 (7) | 0.0022 (4) | −0.0039 (5) | −0.0003 (5) |
O2 | 0.0367 (6) | 0.0365 (6) | 0.0750 (8) | −0.0043 (4) | 0.0046 (5) | −0.0064 (5) |
C1 | 0.0333 (7) | 0.0346 (7) | 0.0347 (7) | −0.0018 (5) | 0.0067 (5) | 0.0000 (5) |
C2 | 0.0304 (6) | 0.0349 (6) | 0.0295 (6) | 0.0015 (5) | 0.0054 (5) | 0.0012 (5) |
C3 | 0.0296 (6) | 0.0334 (7) | 0.0335 (7) | 0.0021 (5) | 0.0031 (5) | 0.0020 (5) |
C4 | 0.0296 (6) | 0.0368 (7) | 0.0288 (6) | 0.0004 (5) | 0.0040 (5) | 0.0010 (5) |
C5 | 0.0288 (6) | 0.0469 (8) | 0.0382 (7) | 0.0039 (5) | 0.0045 (5) | −0.0015 (6) |
C6 | 0.0383 (7) | 0.0423 (7) | 0.0394 (7) | 0.0123 (6) | 0.0057 (6) | −0.0025 (6) |
C7 | 0.0416 (7) | 0.0352 (7) | 0.0334 (7) | 0.0047 (6) | 0.0067 (5) | −0.0034 (5) |
Geometric parameters (Å, º) top
P1—O3 | 1.4931 (11) | C1—C2 | 1.4905 (18) |
P1—O4 | 1.4954 (11) | C2—C3 | 1.3855 (18) |
P1—O5 | 1.5593 (12) | C2—C7 | 1.3938 (18) |
P1—H11 | 1.253 (16) | C3—C4 | 1.3823 (18) |
O5—H12 | 0.85 (3) | C3—H3 | 0.978 (16) |
N1—C4 | 1.4657 (17) | C4—C5 | 1.3894 (18) |
N1—H8 | 0.917 (18) | C5—C6 | 1.384 (2) |
N1—H10 | 0.97 (2) | C5—H5 | 1.058 (18) |
N1—H9 | 0.96 (2) | C6—C7 | 1.378 (2) |
O1—C1 | 1.3130 (16) | C6—H6 | 0.938 (15) |
O1—H1 | 0.85 (2) | C7—H7 | 1.016 (18) |
O2—C1 | 1.2169 (16) | | |
| | | |
O3—P1—O4 | 117.80 (6) | C3—C2—C1 | 120.41 (11) |
O3—P1—O5 | 106.45 (7) | C7—C2—C1 | 119.24 (12) |
O4—P1—O5 | 111.21 (6) | C4—C3—C2 | 118.96 (12) |
O3—P1—H11 | 107.8 (7) | C4—C3—H3 | 124.9 (9) |
O4—P1—H11 | 107.8 (7) | C2—C3—H3 | 116.1 (9) |
O5—P1—H11 | 105.1 (7) | C3—C4—C5 | 121.27 (12) |
P1—O5—H12 | 114.9 (17) | C3—C4—N1 | 119.12 (11) |
C4—N1—H8 | 111.4 (11) | C5—C4—N1 | 119.60 (12) |
C4—N1—H10 | 107.8 (12) | C6—C5—C4 | 119.04 (13) |
H8—N1—H10 | 112.3 (18) | C6—C5—H5 | 126.6 (10) |
C4—N1—H9 | 111.6 (12) | C4—C5—H5 | 114.2 (10) |
H8—N1—H9 | 111.9 (16) | C7—C6—C5 | 120.57 (13) |
H10—N1—H9 | 101.3 (17) | C7—C6—H6 | 117.6 (9) |
C1—O1—H1 | 104.4 (12) | C5—C6—H6 | 121.6 (9) |
O2—C1—O1 | 123.71 (13) | C6—C7—C2 | 119.80 (13) |
O2—C1—C2 | 121.38 (12) | C6—C7—H7 | 117.6 (10) |
O1—C1—C2 | 114.89 (11) | C2—C7—H7 | 122.4 (10) |
C3—C2—C7 | 120.34 (12) | | |
| | | |
O2—C1—C2—C3 | −177.61 (14) | C2—C3—C4—N1 | 180.00 (12) |
O1—C1—C2—C3 | 1.0 (2) | C3—C4—C5—C6 | 1.2 (2) |
O2—C1—C2—C7 | 1.4 (2) | N1—C4—C5—C6 | −179.27 (12) |
O1—C1—C2—C7 | −179.99 (12) | C4—C5—C6—C7 | −0.8 (2) |
C7—C2—C3—C4 | −0.6 (2) | C5—C6—C7—C2 | −0.3 (2) |
C1—C2—C3—C4 | 178.32 (12) | C3—C2—C7—C6 | 1.0 (2) |
C2—C3—C4—C5 | −0.5 (2) | C1—C2—C7—C6 | −177.97 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.86 (3) | 1.71 (3) | 2.5590 (19) | 168 (3) |
O(1)—H(1)···O(3)ii | 0.85 (2) | 1.78 (3) | 2.5982 (16) | 161 (2) |
N(1)—H(8)···O(4)iii | 0.92 (2) | 1.86 (2) | 2.7693 (17) | 171 (2) |
N(1)—H(9)···O(2)iv | 0.96 (2) | 1.84 (3) | 2.7865 (17) | 166 (2) |
N(1)—H(10)···O(3)v | 0.97 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.509 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 21224 reflections |
a = 13.0363 (8) Å | θ = 3.4–30.0° |
b = 11.5204 (7) Å | µ = 0.28 mm−1 |
c = 6.6446 (5) Å | T = 320 K |
β = 104.826 (6)° | Plate, brown |
V = 964.69 (11) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2816 independent reflections |
Radiation source: fine-focus sealed tube | 2243 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 30.0°, θmin = 3.6° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −18→18 |
Tmin = 0.901, Tmax = 0.943 | k = −16→16 |
21224 measured reflections | l = −9→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.14 | Δρmax = 0.53 e Å−3 |
2816 reflections | Δρmin = −0.28 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 964.69 (11) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0363 (8) Å | µ = 0.28 mm−1 |
b = 11.5204 (7) Å | T = 320 K |
c = 6.6446 (5) Å | 0.40 × 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 = 0.943 | Rint = 0.035 |
21224 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.149 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.53 e Å−3 |
2816 reflections | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.668 (3) | 0.647 (3) | 0.393 (6) | 0.132 (14)* | |
H3 | 0.4401 (15) | 0.5060 (17) | 0.221 (3) | 0.041 (5)* | |
H5 | 0.1291 (19) | 0.6114 (19) | 0.015 (3) | 0.049 (5)* | |
H6 | 0.1937 (15) | 0.8151 (16) | 0.100 (3) | 0.038 (5)* | |
H7 | 0.375 (2) | 0.851 (2) | 0.223 (4) | 0.067 (7)* | |
H8 | 0.1937 (18) | 0.420 (2) | −0.066 (4) | 0.055 (6)* | |
H9 | 0.297 (3) | 0.375 (2) | 0.072 (4) | 0.084 (9)* | |
H10 | 0.211 (2) | 0.400 (2) | 0.163 (4) | 0.064 (7)* | |
H12 | −0.008 (3) | 0.019 (3) | −0.195 (5) | 0.109 (11)* | |
H11 | 0.0519 (17) | 0.2304 (18) | −0.026 (3) | 0.052 (6)* | |
P1 | 0.10470 (3) | 0.13499 (4) | −0.01712 (6) | 0.03810 (17) | |
O3 | 0.20999 (9) | 0.16725 (12) | −0.0507 (2) | 0.0486 (3) | |
O4 | 0.10345 (11) | 0.06893 (13) | 0.17557 (18) | 0.0570 (4) | |
O5 | 0.04403 (12) | 0.06834 (16) | −0.2163 (2) | 0.0676 (5) | |
N1 | 0.24265 (11) | 0.42475 (12) | 0.0671 (2) | 0.0382 (3) | |
O1 | 0.59814 (10) | 0.61106 (11) | 0.3536 (2) | 0.0507 (3) | |
O2 | 0.56797 (10) | 0.80092 (10) | 0.3658 (2) | 0.0548 (4) | |
C1 | 0.53650 (12) | 0.70252 (13) | 0.3221 (2) | 0.0368 (3) | |
C2 | 0.42188 (12) | 0.67765 (13) | 0.2324 (2) | 0.0338 (3) | |
C3 | 0.38678 (12) | 0.56431 (13) | 0.1906 (2) | 0.0349 (3) | |
C4 | 0.27962 (11) | 0.54398 (13) | 0.1120 (2) | 0.0349 (3) | |
C5 | 0.20654 (13) | 0.63421 (15) | 0.0749 (3) | 0.0405 (4) | |
C6 | 0.24265 (14) | 0.74709 (16) | 0.1160 (3) | 0.0440 (4) | |
C7 | 0.34984 (13) | 0.76929 (14) | 0.1933 (2) | 0.0392 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0293 (2) | 0.0436 (3) | 0.0385 (3) | −0.00505 (14) | 0.00343 (16) | 0.00286 (15) |
O3 | 0.0291 (6) | 0.0571 (7) | 0.0564 (8) | −0.0071 (5) | 0.0050 (5) | 0.0035 (6) |
O4 | 0.0554 (8) | 0.0737 (9) | 0.0343 (6) | −0.0298 (7) | −0.0024 (5) | 0.0032 (6) |
O5 | 0.0659 (9) | 0.0969 (12) | 0.0340 (7) | −0.0440 (9) | 0.0018 (6) | 0.0011 (6) |
N1 | 0.0327 (6) | 0.0409 (7) | 0.0375 (7) | −0.0037 (5) | 0.0027 (5) | −0.0006 (5) |
O1 | 0.0344 (6) | 0.0395 (6) | 0.0692 (9) | 0.0026 (5) | −0.0035 (6) | −0.0007 (6) |
O2 | 0.0398 (6) | 0.0382 (7) | 0.0809 (10) | −0.0047 (5) | 0.0053 (6) | −0.0070 (6) |
C1 | 0.0347 (7) | 0.0352 (7) | 0.0384 (8) | −0.0010 (5) | 0.0058 (6) | 0.0011 (6) |
C2 | 0.0325 (7) | 0.0349 (7) | 0.0323 (7) | 0.0002 (5) | 0.0054 (5) | −0.0008 (5) |
C3 | 0.0314 (7) | 0.0344 (7) | 0.0363 (7) | 0.0022 (5) | 0.0037 (5) | 0.0013 (6) |
C4 | 0.0311 (7) | 0.0392 (7) | 0.0321 (7) | 0.0002 (5) | 0.0041 (5) | 0.0005 (6) |
C5 | 0.0303 (7) | 0.0479 (9) | 0.0405 (8) | 0.0046 (6) | 0.0041 (6) | −0.0013 (6) |
C6 | 0.0407 (8) | 0.0461 (9) | 0.0428 (8) | 0.0122 (7) | 0.0064 (7) | −0.0017 (7) |
C7 | 0.0438 (8) | 0.0358 (7) | 0.0363 (8) | 0.0048 (6) | 0.0070 (6) | −0.0031 (6) |
Geometric parameters (Å, º) top
P1—O3 | 1.4930 (12) | C1—C2 | 1.488 (2) |
P1—O4 | 1.4932 (13) | C2—C3 | 1.388 (2) |
P1—O5 | 1.5590 (14) | C2—C7 | 1.393 (2) |
P1—H11 | 1.29 (2) | C3—C4 | 1.380 (2) |
O5—H12 | 0.92 (4) | C3—H3 | 0.950 (19) |
N1—C4 | 1.461 (2) | C4—C5 | 1.389 (2) |
N1—H8 | 0.95 (2) | C5—C6 | 1.386 (2) |
N1—H10 | 0.89 (3) | C5—H5 | 1.02 (2) |
N1—H9 | 0.90 (3) | C6—C7 | 1.384 (2) |
O1—C1 | 1.3091 (19) | C6—H6 | 0.999 (19) |
O1—H1 | 0.97 (4) | C7—H7 | 1.00 (3) |
O2—C1 | 1.2152 (19) | | |
| | | |
O3—P1—O4 | 117.87 (8) | C3—C2—C1 | 120.47 (14) |
O3—P1—O5 | 106.36 (8) | C7—C2—C1 | 119.27 (14) |
O4—P1—O5 | 111.24 (8) | C4—C3—C2 | 119.02 (14) |
O3—P1—H11 | 106.3 (9) | C4—C3—H3 | 125.0 (11) |
O4—P1—H11 | 110.6 (9) | C2—C3—H3 | 115.9 (11) |
O5—P1—H11 | 103.4 (9) | C3—C4—C5 | 121.47 (14) |
P1—O5—H12 | 114 (2) | C3—C4—N1 | 119.07 (13) |
C4—N1—H8 | 110.7 (14) | C5—C4—N1 | 119.46 (13) |
C4—N1—H10 | 110.0 (15) | C6—C5—C4 | 118.96 (15) |
H8—N1—H10 | 109 (2) | C6—C5—H5 | 124.8 (13) |
C4—N1—H9 | 111.9 (18) | C4—C5—H5 | 116.2 (13) |
H8—N1—H9 | 109 (2) | C7—C6—C5 | 120.42 (15) |
H10—N1—H9 | 106 (2) | C7—C6—H6 | 116.9 (11) |
C1—O1—H1 | 101 (2) | C5—C6—H6 | 122.6 (11) |
O2—C1—O1 | 123.83 (15) | C6—C7—C2 | 119.86 (15) |
O2—C1—C2 | 121.22 (14) | C6—C7—H7 | 120.1 (15) |
O1—C1—C2 | 114.92 (13) | C2—C7—H7 | 120.0 (15) |
C3—C2—C7 | 120.26 (14) | | |
| | | |
O2—C1—C2—C7 | 1.6 (2) | C2—C3—C4—N1 | 179.71 (14) |
O1—C1—C2—C7 | 179.94 (14) | C3—C4—C5—C6 | 0.7 (3) |
O2—C1—C2—C3 | −177.57 (16) | N1—C4—C5—C6 | −179.30 (15) |
O1—C1—C2—C3 | 0.8 (2) | C4—C5—C6—C7 | −0.2 (3) |
C7—C2—C3—C4 | −0.6 (2) | C5—C6—C7—C2 | −0.7 (3) |
C1—C2—C3—C4 | 178.47 (14) | C3—C2—C7—C6 | 1.1 (2) |
C2—C3—C4—C5 | −0.3 (2) | C1—C2—C7—C6 | −177.99 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.92 (4) | 1.64 (4) | 2.557 (2) | 176 (3) |
O(1)—H(1)···O(3)ii | 0.97 (4) | 1.68 (4) | 2.5912 (18) | 154 (3) |
N(1)—H(8)···O(4)iii | 0.95 (3) | 1.82 (3) | 2.7659 (18) | 173 (2) |
N(1)—H(9)···O(2)iv | 0.91 (3) | 1.90 (4) | 2.787 (2) | 165 (2) |
N(1)—H(10)···O(3)v | 0.88 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Crystal data top
(C7H8NO2)+·(H2PO3)− | F(000) = 456 |
Mr = 219.13 | Dx = 1.510 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 24042 reflections |
a = 13.0221 (11) Å | θ = 3.4–30.0° |
b = 11.5012 (8) Å | µ = 0.28 mm−1 |
c = 6.6489 (5) Å | T = 345 K |
β = 104.614 (7)° | Plate, brown |
V = 963.59 (13) Å3 | 0.40 × 0.40 × 0.20 mm |
Z = 4 | |
Data collection top
Xcalibur-Saphire2 diffractometer | 2815 independent reflections |
Radiation source: fine-focus sealed tube | 2224 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω scans | θmax = 30.0°, θmin = 3.5° |
Absorption correction: integration Absorb, (DeTitta, 1985) | h = −18→18 |
Tmin = 0.896, Tmax = 0.946 | k = −16→16 |
24042 measured reflections | l = −9→8 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H 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 = 1.12 | Δρmax = 0.49 e Å−3 |
2815 reflections | Δρmin = −0.26 e Å−3 |
167 parameters | |
Crystal data top
(C7H8NO2)+·(H2PO3)− | V = 963.59 (13) Å3 |
Mr = 219.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0221 (11) Å | µ = 0.28 mm−1 |
b = 11.5012 (8) Å | T = 345 K |
c = 6.6489 (5) Å | 0.40 × 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 = 0.946 | Rint = 0.049 |
24042 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.49 e Å−3 |
2815 reflections | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H1 | 0.160 (4) | 0.850 (3) | 0.281 (6) | 0.137 (15)* | |
H3 | −0.0607 (15) | 0.9954 (17) | 0.220 (3) | 0.041 (5)* | |
H5 | −0.371 (2) | 0.888 (2) | 0.113 (3) | 0.054 (6)* | |
H6 | −0.3047 (16) | 0.6846 (17) | 0.099 (3) | 0.042 (5)* | |
H7 | −0.123 (2) | 0.647 (2) | 0.157 (4) | 0.063 (7)* | |
H8 | −0.3064 (19) | 1.080 (2) | 0.266 (4) | 0.060 (6)* | |
H9 | −0.290 (2) | 1.101 (2) | 0.050 (4) | 0.071 (7)* | |
H10 | −0.207 (2) | 1.121 (2) | 0.230 (4) | 0.074 (8)* | |
H11 | 0.4476 (16) | 0.7730 (18) | 0.422 (3) | 0.049 (5)* | |
H12 | 0.508 (3) | 0.982 (3) | 0.310 (5) | 0.115 (11)* | |
P1 | 0.39507 (3) | 0.86539 (4) | 0.37837 (7) | 0.04097 (18) | |
O3 | 0.28998 (9) | 0.83314 (13) | 0.2400 (2) | 0.0532 (3) | |
O4 | 0.39668 (11) | 0.93119 (13) | 0.5722 (2) | 0.0614 (4) | |
O5 | 0.45540 (13) | 0.93216 (17) | 0.2401 (2) | 0.0733 (5) | |
N1 | −0.25777 (12) | 1.07453 (13) | 0.1750 (3) | 0.0414 (3) | |
O1 | 0.09802 (11) | 0.88877 (11) | 0.2449 (3) | 0.0548 (4) | |
O2 | 0.06828 (11) | 0.69896 (11) | 0.2047 (3) | 0.0592 (4) | |
C1 | 0.03659 (13) | 0.79736 (14) | 0.2158 (3) | 0.0397 (4) | |
C2 | −0.07796 (12) | 0.82181 (14) | 0.1908 (2) | 0.0366 (3) | |
C3 | −0.11340 (12) | 0.93524 (13) | 0.1968 (3) | 0.0377 (3) | |
C4 | −0.22054 (12) | 0.95509 (14) | 0.1677 (2) | 0.0373 (3) | |
C5 | −0.29333 (14) | 0.86462 (15) | 0.1326 (3) | 0.0439 (4) | |
C6 | −0.25680 (14) | 0.75218 (16) | 0.1287 (3) | 0.0476 (4) | |
C7 | −0.14988 (14) | 0.73004 (15) | 0.1585 (3) | 0.0424 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0317 (2) | 0.0462 (3) | 0.0462 (3) | −0.00520 (14) | 0.01193 (19) | −0.00585 (16) |
O3 | 0.0320 (6) | 0.0617 (8) | 0.0650 (8) | −0.0080 (5) | 0.0105 (6) | −0.0085 (6) |
O4 | 0.0602 (8) | 0.0785 (10) | 0.0553 (8) | −0.0317 (7) | 0.0329 (7) | −0.0195 (7) |
O5 | 0.0708 (10) | 0.1053 (13) | 0.0534 (8) | −0.0471 (10) | 0.0334 (8) | −0.0250 (8) |
N1 | 0.0362 (7) | 0.0436 (8) | 0.0468 (8) | 0.0037 (6) | 0.0150 (6) | 0.0015 (6) |
O1 | 0.0375 (7) | 0.0421 (7) | 0.0880 (10) | −0.0023 (5) | 0.0219 (7) | −0.0021 (6) |
O2 | 0.0426 (7) | 0.0411 (7) | 0.0931 (11) | 0.0056 (5) | 0.0160 (7) | −0.0048 (7) |
C1 | 0.0377 (8) | 0.0379 (8) | 0.0446 (8) | 0.0007 (6) | 0.0122 (6) | 0.0020 (6) |
C2 | 0.0356 (7) | 0.0370 (7) | 0.0387 (7) | −0.0008 (6) | 0.0124 (6) | −0.0012 (6) |
C3 | 0.0340 (7) | 0.0365 (7) | 0.0445 (8) | −0.0021 (6) | 0.0131 (6) | 0.0004 (6) |
C4 | 0.0340 (7) | 0.0412 (8) | 0.0386 (8) | −0.0001 (6) | 0.0127 (6) | 0.0006 (6) |
C5 | 0.0334 (8) | 0.0522 (9) | 0.0471 (9) | −0.0054 (6) | 0.0121 (7) | −0.0038 (7) |
C6 | 0.0443 (9) | 0.0491 (9) | 0.0506 (9) | −0.0135 (7) | 0.0145 (7) | −0.0088 (7) |
C7 | 0.0472 (9) | 0.0385 (8) | 0.0440 (9) | −0.0053 (6) | 0.0162 (7) | −0.0056 (6) |
Geometric parameters (Å, º) top
P1—O3 | 1.4904 (13) | C1—C2 | 1.486 (2) |
P1—O4 | 1.4898 (14) | C2—C3 | 1.388 (2) |
P1—O5 | 1.5543 (15) | C2—C7 | 1.391 (2) |
P1—H11 | 1.26 (2) | C3—C4 | 1.378 (2) |
O5—H12 | 0.93 (4) | C3—H3 | 0.959 (19) |
N1—C4 | 1.462 (2) | C4—C5 | 1.387 (2) |
N1—H8 | 0.98 (3) | C5—C6 | 1.380 (3) |
N1—H9 | 0.89 (3) | C5—H5 | 1.02 (2) |
N1—H10 | 0.86 (3) | C6—C7 | 1.380 (2) |
O1—C1 | 1.306 (2) | C6—H6 | 0.985 (19) |
O1—H1 | 0.90 (4) | C7—H7 | 1.02 (2) |
O2—C1 | 1.213 (2) | | |
| | | |
O3—P1—O4 | 118.07 (8) | C3—C2—C1 | 120.44 (14) |
O3—P1—O5 | 106.28 (9) | C7—C2—C1 | 119.44 (14) |
O4—P1—O5 | 111.19 (8) | C4—C3—C2 | 118.94 (14) |
O4—P1—H11 | 110.0 (9) | C4—C3—H3 | 124.1 (11) |
O3—P1—H11 | 107.1 (9) | C2—C3—H3 | 116.9 (11) |
O5—P1—H11 | 103.1 (9) | C3—C4—C5 | 121.59 (15) |
P1—O5—H12 | 116 (2) | C3—C4—N1 | 118.92 (14) |
C4—N1—H8 | 110.5 (14) | C5—C4—N1 | 119.49 (14) |
C4—N1—H9 | 112.2 (16) | C6—C5—C4 | 118.80 (15) |
C4—N1—H10 | 112.1 (18) | C6—C5—H5 | 125.5 (13) |
H8—N1—H9 | 110 (2) | C4—C5—H5 | 115.7 (13) |
H8—N1—H10 | 104 (2) | C7—C6—C5 | 120.69 (15) |
H10—N1—H9 | 108 (2) | C7—C6—H6 | 116.6 (11) |
C1—O1—H1 | 97 (3) | C5—C6—H6 | 122.7 (11) |
O2—C1—O1 | 123.72 (16) | C6—C7—C2 | 119.85 (16) |
O2—C1—C2 | 121.14 (14) | C6—C7—H7 | 120.8 (14) |
O1—C1—C2 | 115.12 (14) | C2—C7—H7 | 119.3 (14) |
C3—C2—C7 | 120.12 (15) | | |
| | | |
C7—C2—C1—O2 | 1.4 (3) | C1—C2—C7—C6 | −177.98 (16) |
C7—C2—C1—O1 | 179.87 (15) | C2—C3—C4—C5 | 0.0 (2) |
C3—C2—C1—O2 | −177.80 (16) | C2—C3—C4—N1 | 179.76 (14) |
C3—C2—C1—O1 | 0.7 (2) | C6—C5—C4—C3 | 0.5 (3) |
C7—C2—C3—C4 | −0.9 (2) | C6—C5—C4—N1 | −179.23 (16) |
C1—C2—C3—C4 | 178.33 (15) | C2—C7—C6—C5 | −0.7 (3) |
C3—C2—C7—C6 | 1.2 (2) | C4—C5—C6—C7 | −0.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.92 (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)ii | 0.98 (3) | 1.79 (3) | 2.764 (2) | 172 (2) |
N(1)—H(10)···O(2)iii | 0.86 (2) | 1.96 (3) | 2.789 (2) | 161 (2) |
N(1)—H(9)···O(3)iv | 0.89 (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)− |
Mr | 219.13 | 219.13 | 219.13 | 219.13 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 100 | 130 | 170 | 210 |
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) |
V (Å3) | 948.35 (11) | 943.67 (9) | 947.62 (9) | 948.21 (10) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.29 | 0.29 | 0.29 | 0.29 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 |
|
Data collection |
Diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.908, 0.938 | 0.908, 0.938 | 0.890, 0.942 | 0.887, 0.935 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 78938, 2751, 2731 | 23422, 2732, 2424 | 23509, 2739, 2382 | 23560, 2747, 2346 |
Rint | 0.032 | 0.031 | 0.031 | 0.032 |
(sin θ/λ)max (Å−1) | 0.703 | 0.703 | 0.703 | 0.703 |
|
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 reflections | 2751 | 2732 | 2739 | 2747 |
No. of parameters | 165 | 167 | 167 | 167 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.56, −0.32 | 0.44, −0.29 | 0.41, −0.27 | 0.39, −0.25 |
| (235K) | (255K) | (293K) | (320K) |
Crystal data |
Chemical formula | (C7H8NO2)+·(H2PO3)− | (C7H8NO2)+·(H2PO3)− | (C7H8NO2)+·(H2PO3)− | (C7H8NO2)+·(H2PO3)− |
Mr | 219.13 | 219.13 | 219.13 | 219.13 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 235 | 255 | 293 | 320 |
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) |
V (Å3) | 952.90 (12) | 963.57 (18) | 965.4 (4) | 964.69 (11) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.29 | 0.28 | 0.28 | 0.28 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 |
|
Data collection |
Diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.889, 0.940 | 0.872, 0.946 | 0.896, 0.946 | 0.901, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23700, 2765, 2311 | 25199, 2814, 2432 | 26411, 2807, 2063 | 21224, 2816, 2243 |
Rint | 0.033 | 0.056 | 0.041 | 0.035 |
(sin θ/λ)max (Å−1) | 0.703 | 0.703 | 0.703 | 0.703 |
|
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 reflections | 2765 | 2814 | 2807 | 2816 |
No. of parameters | 167 | 167 | 165 | 167 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.27 | 0.39, −0.39 | 0.27, −0.34 | 0.53, −0.28 |
| (345K) |
Crystal data |
Chemical formula | (C7H8NO2)+·(H2PO3)− |
Mr | 219.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 345 |
a, b, c (Å) | 13.0221 (11), 11.5012 (8), 6.6489 (5) |
β (°) | 104.614 (7) |
V (Å3) | 963.59 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 |
|
Data collection |
Diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.896, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24042, 2815, 2224 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.156, 1.12 |
No. of reflections | 2815 |
No. of parameters | 167 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.49, −0.26 |
Selected torsion angles (º) for (100K) topO2—C1—C2—C7 | −4.22 (14) | O2—C1—C2—C3 | 175.79 (9) |
O1—C1—C2—C7 | 174.61 (9) | O1—C1—C2—C3 | −5.38 (14) |
Hydrogen-bond geometry (Å, º) for (100K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.979 (19) | 1.570 (19) | 2.5456 (11) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 0.901 (17) | 1.702 (18) | 2.5977 (11) | 172.3 (18) |
N(1)—H(8)···O(4)iii | 0.895 (19) | 1.909 (19) | 2.7966 (12) | 170.9 (18) |
N(1)—H(9)···O(2)iv | 0.850 (19) | 1.982 (19) | 2.8097 (12) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.879 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (130K) topO2—C1—C2—C7 | −4.35 (17) | O2—C1—C2—C3 | 175.84 (11) |
O1—C1—C2—C7 | 174.68 (10) | O1—C1—C2—C3 | −5.12 (16) |
Hydrogen-bond geometry (Å, º) for (130K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 1.00 (2) | 1.54 (2) | 2.5386 (13) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 0.87 (3) | 1.73 (2) | 2.5919 (12) | 172.3 (18) |
N(1)—H(8)···O(4)iii | 0.895 (19) | 1.883 (19) | 2.7916 (14) | 170.9 (18) |
N(1)—H(9)···O(2)iv | 0.879 (19) | 1.948 (19) | 2.8037 (13) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.879 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (170K) topO2—C1—C2—C7 | −4.23 (18) | O2—C1—C2—C3 | 176.04 (12) |
O1—C1—C2—C7 | 174.95 (11) | O1—C1—C2—C3 | −4.78 (17) |
Hydrogen-bond geometry (Å, º) for (170K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.98 (4) | 1.56 (4) | 2.5390 (14) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 0.85 (3) | 1.75 (2) | 2.5930 (13) | 172.3 (18) |
N(1)—H(8)···O(4)iii | 0.931 (19) | 1.868 (19) | 2.7941 (14) | 173.0 (16) |
N(1)—H(9)···O(2)iv | 0.878 (19) | 1.949 (19) | 2.8045 (14) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.879 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (210K) topO2—C1—C2—C7 | −4.02 (19) | O2—C1—C2—C3 | 176.23 (12) |
O1—C1—C2—C7 | 175.19 (11) | O1—C1—C2—C3 | −4.56 (18) |
Hydrogen-bond geometry (Å, º) for (210K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.97 (4) | 1.57 (4) | 2.5367 (14) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 0.84 (3) | 1.76 (2) | 2.5900 (14) | 172.3 (18) |
N(1)—H(8)···O(4)iii | 0.945 (18) | 1.853 (19) | 2.7901 (15) | 170.9 (18) |
N(1)—H(9)···O(2)iv | 0.892 (19) | 1.934 (19) | 2.8035 (12) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.901 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (235K) topO2—C1—C2—C7 | −3.9 (2) | O2—C1—C2—C3 | 176.46 (12) |
O1—C1—C2—C7 | 175.41 (12) | O1—C1—C2—C3 | −4.28 (19) |
Hydrogen-bond geometry (Å, º) for (235K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.94 (4) | 1.61 (4) | 2.5394 (15) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 0.81 (2) | 1.79 (2) | 2.5931 (14) | 172.3 (18) |
N(1)—H(8)···O(4)iii | 0.956 (19) | 1.842 (19) | 2.7933 (15) | 172.9 (15) |
N(1)—H(9)···O(2)iv | 0.892 (19) | 1.935 (19) | 2.8048 (15) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.916 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (255K) topO2—C1—C2—C7 | 1.7 (2) | O2—C1—C2—C3 | −177.26 (15) |
O1—C1—C2—C7 | 179.98 (14) | O1—C1—C2—C3 | 1.0 (2) |
Hydrogen-bond geometry (Å, º) for (255K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.88 (4) | 1.69 (4) | 2.556 (2) | 173.4 (18) |
O(1)—H(1)···O(3)ii | 1.01 (5) | 1.63 (5) | 2.5977 (11) | 160 (4) |
N(1)—H(8)···O(4)iii | 0.96 (3) | 1.83 (3) | 2.7704 (18) | 170.9 (18) |
N(1)—H(9)···O(2)iv | 0.93 (2) | 1.90 (3) | 2.7885 (19) | 159 (2) |
N(1)—H(10)···O(3)v | 0.91 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (293K) topO2—C1—C2—C3 | −177.61 (14) | O2—C1—C2—C7 | 1.4 (2) |
O1—C1—C2—C3 | 1.0 (2) | O1—C1—C2—C7 | −179.99 (12) |
Hydrogen-bond geometry (Å, º) for (293K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.86 (3) | 1.71 (3) | 2.5590 (19) | 168 (3) |
O(1)—H(1)···O(3)ii | 0.85 (2) | 1.78 (3) | 2.5982 (16) | 161.1 (19) |
N(1)—H(8)···O(4)iii | 0.917 (19) | 1.860 (19) | 2.7693 (17) | 170.9 (16) |
N(1)—H(9)···O(2)iv | 0.96 (2) | 1.84 (3) | 2.7865 (17) | 166 (2) |
N(1)—H(10)···O(3)v | 0.97 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (320K) topO2—C1—C2—C7 | 1.6 (2) | O2—C1—C2—C3 | −177.57 (16) |
O1—C1—C2—C7 | 179.94 (14) | O1—C1—C2—C3 | 0.8 (2) |
Hydrogen-bond geometry (Å, º) for (320K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.92 (4) | 1.64 (4) | 2.557 (2) | 176 (3) |
O(1)—H(1)···O(3)ii | 0.97 (4) | 1.68 (4) | 2.5912 (18) | 154 (3) |
N(1)—H(8)···O(4)iii | 0.95 (3) | 1.82 (3) | 2.7659 (18) | 173 (2) |
N(1)—H(9)···O(2)iv | 0.91 (3) | 1.90 (4) | 2.787 (2) | 164.5 (18) |
N(1)—H(10)···O(3)v | 0.879 (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, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2. |
Selected torsion angles (º) for (345K) topC7—C2—C1—O2 | 1.4 (3) | C3—C2—C1—O2 | −177.80 (16) |
C7—C2—C1—O1 | 179.87 (15) | C3—C2—C1—O1 | 0.7 (2) |
Hydrogen-bond geometry (Å, º) for (345K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(12)···O(4)i | 0.92 (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)ii | 0.98 (3) | 1.79 (3) | 2.764 (2) | 172 (2) |
N(1)—H(10)···O(2)iii | 0.86 (2) | 1.96 (3) | 2.789 (2) | 161 (2) |
N(1)—H(9)···O(3)iv | 0.89 (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. |