Crystals of
m-carboxyphenylammonium monohydrogenphosphite, C
7H
8NO
·H
2PO
(
m-CPAMP), space group
P2
/
c, grown from aqueous solution undergo a reversible first-order single-crystal phase transition at
Tc = 246 (2) K with a hysteresis of 3.6 K. The thermal behaviour of the sample was characterized by differential scanning calorimetry (DSC) experiments. Variations of the unit-cell parameters
versus temperature between 100 and 320 K are reported. The transition from the higher-temperature phase (HTP) to the lower-temperature phase (LTP) is characterized by a unit-cell volume contraction of 1.77%. The average structure and unit-cell packing of
m-CPAMP at lower temperature (100 K) are reported from accurate X-ray data sets and compared with those of the higher-temperature phase (293 K) in order to investigate the mechanism of the phase transition. The reciprocal lattice reconstruction showed a few very weak satellite reflections which will be discussed in a forthcoming paper.
Supporting information
CCDC references: 292332; 292333
For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); 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 9599 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)* | |
H12 | 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) | |
H11 | −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—H12 | 1.307 (16) | C3—C4 | 1.3914 (13) |
O5—H11 | 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—H12 | 108.3 (7) | C4—C3—H3 | 119.7 (10) |
O4—P1—H12 | 107.6 (7) | C2—C3—H3 | 122.0 (10) |
O5—P1—H12 | 104.6 (7) | C3—C4—C5 | 121.94 (9) |
P1—O5—H11 | 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(11)···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 = 1.508 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9599 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)* | |
H12 | 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) | |
H11 | 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—H12 | 1.253 (16) | C3—C4 | 1.3823 (18) |
O5—H11 | 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—H12 | 107.8 (7) | C4—C3—H3 | 124.9 (9) |
O4—P1—H12 | 107.8 (7) | C2—C3—H3 | 116.1 (9) |
O5—P1—H12 | 105.1 (7) | C3—C4—C5 | 121.27 (12) |
P1—O5—H11 | 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(11)···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. |
Experimental details
| (m-CPAMP_100K) | (m-CPAMP_293K) |
Crystal data |
Chemical formula | (C7H8NO2)+·(H2PO3)− | (C7H8NO2)+·(H2PO3)− |
Mr | 219.13 | 219.13 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 100 | 293 |
a, b, c (Å) | 12.1405 (7), 12.4273 (9), 6.3851 (4) | 13.036 (3), 11.538 (2), 6.6366 (13) |
β (°) | 100.122 (5) | 104.73 (3) |
V (Å3) | 948.35 (11) | 965.4 (4) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.29 | 0.28 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 | 0.40 × 0.40 × 0.20 |
|
Data collection |
Diffractometer | Xcalibur-Saphire2 diffractometer | Xcalibur-Saphire2 diffractometer |
Absorption correction | Integration Absorb, (DeTitta, 1985) | Integration Absorb, (DeTitta, 1985) |
Tmin, Tmax | 0.908, 0.938 | 0.896, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 78938, 2751, 2731 | 26411, 2807, 2063 |
Rint | 0.032 | 0.041 |
(sin θ/λ)max (Å−1) | 0.703 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.094, 1.08 | 0.037, 0.103, 0.99 |
No. of reflections | 2751 | 2807 |
No. of parameters | 165 | 165 |
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 |
Δρmax, Δρmin (e Å−3) | 0.56, −0.32 | 0.27, −0.34 |
Selected torsion angles (º) for (m-CPAMP_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 (m-CPAMP_100K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(11)···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 (m-CPAMP_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 (m-CPAMP_293K) top
D—H···A | D—H | H···A | D···A | D—H···A |
O(5)—H(11)···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. |