Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021808/na6121sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021808/na6121Isup2.hkl |
CCDC reference: 180774
Data collection: KM4B8 (Gałdecki et al., 1997); cell refinement: LATCO (Allmann, 1988); data reduction: JANA2000 (Petříček & Dušek, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996).
C7H9ClN+·H2PO4− | F(000) = 496 |
Mr = 239.59 | In the setting corresponding to C1121/b it has nearly orthorhombic setting. |
Monoclinic, P21/c | Dx = 1.497 Mg m−3 |
Hall symbol: -P2ybc | Mo Kα radiation, λ = 0.710688 Å |
a = 16.603 (4) Å | Cell parameters from 18 reflections |
b = 8.339 (3) Å | θ = 2.8–15.8° |
c = 7.903 (4) Å | µ = 0.50 mm−1 |
β = 103.76 (6)° | T = 290 K |
V = 1062.8 (7) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.14 × 0.06 mm |
Kuma KM-4 diffractometer | Rint = 0.141 |
ω–2θ scans | θmax = 26.3°, θmin = 1.3° |
Absorption correction: integration Gaussian integration (Coppens, 1965) | h = −20→20 |
Tmin = 0.919, Tmax = 0.977 | k = −10→0 |
4283 measured reflections | l = −9→9 |
2151 independent reflections | 3 standard reflections every 200 reflections |
911 reflections with I > 2σ(I) | intensity decay: 9.8% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.170 | w = 1/[σ2(Fo2) + (0.1P)2 + ] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max = 0.001 |
2151 reflections | Δρmax = 0.23 e Å−3 |
132 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (3) |
Experimental. The diffractions of the studied crystals were invariably split except for the diffractions 00 l. No domains, however, were observed in the microscope in the polarized light. Because of this splitting the lattice parameters were determined from the powder pattern. The powder diffractometer used is a locally adapted parallel beam HUBER powder diffractometer equipped with Goebel mirror and double crystal monochromator in reflected beam. The source is rotation-anode (Cu) radiation generated by 55 kV/300 mA; step scan mode with 5 - s step 0.02 ° in 2θ. The data collection was performed in the unit cell with C-centered orthorhombic metric (see the section _publ_section_comment). The parameters of the scan were chosen so the split peaks fell between the background regions, and therefore they were integrated together. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.43529 (8) | 0.03782 (14) | 0.20760 (16) | 0.0370 (4) | |
O3 | 0.52042 (19) | 0.0964 (4) | 0.2029 (4) | 0.0407 (8) | |
O1 | 0.4420 (3) | −0.1045 (4) | 0.3391 (5) | 0.0508 (9) | |
H1 | 0.4610 | −0.1834 | 0.3003 | 0.076* | |
O2 | 0.3906 (2) | −0.0258 (5) | 0.0236 (4) | 0.0537 (10) | |
H2 | 0.4250 | −0.0429 | −0.0334 | 0.081* | |
O4 | 0.3801 (2) | 0.1578 (4) | 0.2637 (4) | 0.0479 (9) | |
Cl | 0.02954 (12) | 0.7927 (3) | −0.0569 (3) | 0.1069 (8) | |
N | 0.3438 (2) | 0.4280 (4) | 0.0670 (5) | 0.0388 (10) | |
H1N | 0.3849 | 0.4935 | 0.1173 | 0.058* | |
H2N | 0.3518 | 0.3944 | −0.0346 | 0.058* | |
H3N | 0.3428 | 0.3440 | 0.1360 | 0.058* | |
C1 | 0.2655 (3) | 0.5128 (6) | 0.0384 (6) | 0.0403 (12) | |
C2 | 0.1921 (3) | 0.4343 (6) | −0.0326 (7) | 0.0530 (14) | |
C3 | 0.1192 (4) | 0.5239 (8) | −0.0615 (8) | 0.0675 (17) | |
H3 | 0.0687 | 0.4749 | −0.1108 | 0.081* | |
C4 | 0.1210 (4) | 0.6838 (8) | −0.0179 (8) | 0.0659 (17) | |
C5 | 0.1936 (4) | 0.7599 (8) | 0.0538 (10) | 0.0760 (19) | |
H5 | 0.1943 | 0.8679 | 0.0834 | 0.091* | |
C6 | 0.2665 (4) | 0.6728 (6) | 0.0817 (8) | 0.0597 (16) | |
H6 | 0.3167 | 0.7228 | 0.1303 | 0.072* | |
C7 | 0.1901 (4) | 0.2564 (7) | −0.0783 (10) | 0.080 (2) | |
H1C7 | 0.2294 | 0.2352 | −0.1472 | 0.120* | |
H2C7 | 0.1355 | 0.2277 | −0.1433 | 0.120* | |
H3C7 | 0.2042 | 0.1942 | 0.0268 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0497 (8) | 0.0241 (6) | 0.0401 (7) | 0.0002 (6) | 0.0162 (5) | 0.0005 (6) |
O3 | 0.048 (2) | 0.0318 (17) | 0.0438 (19) | −0.0026 (16) | 0.0132 (15) | −0.0031 (14) |
O1 | 0.080 (3) | 0.0277 (17) | 0.052 (2) | 0.0044 (18) | 0.0301 (18) | 0.0022 (15) |
O2 | 0.049 (2) | 0.067 (2) | 0.0457 (19) | −0.013 (2) | 0.0132 (16) | −0.0116 (19) |
O4 | 0.063 (2) | 0.0342 (18) | 0.053 (2) | 0.0111 (17) | 0.0264 (18) | 0.0071 (16) |
Cl | 0.0742 (13) | 0.1020 (16) | 0.1401 (18) | 0.0406 (12) | 0.0167 (12) | 0.0085 (13) |
N | 0.047 (2) | 0.031 (2) | 0.041 (2) | −0.0005 (18) | 0.0144 (18) | 0.0045 (16) |
C1 | 0.043 (3) | 0.037 (3) | 0.043 (3) | 0.002 (2) | 0.015 (2) | 0.002 (2) |
C2 | 0.053 (4) | 0.048 (3) | 0.057 (3) | −0.004 (3) | 0.011 (3) | −0.001 (3) |
C3 | 0.053 (4) | 0.070 (4) | 0.076 (4) | −0.003 (3) | 0.010 (3) | −0.003 (3) |
C4 | 0.053 (4) | 0.071 (4) | 0.071 (4) | 0.018 (3) | 0.010 (3) | 0.010 (3) |
C5 | 0.072 (5) | 0.046 (3) | 0.108 (5) | 0.007 (3) | 0.017 (4) | −0.006 (4) |
C6 | 0.052 (4) | 0.036 (3) | 0.087 (4) | −0.003 (3) | 0.007 (3) | −0.006 (3) |
C7 | 0.071 (5) | 0.053 (4) | 0.109 (5) | −0.016 (3) | 0.009 (4) | −0.025 (4) |
P1—O4 | 1.493 (4) | C1—C2 | 1.379 (7) |
P1—O3 | 1.504 (3) | C2—C3 | 1.395 (8) |
P1—O2 | 1.560 (4) | C2—C7 | 1.526 (8) |
P1—O1 | 1.564 (3) | C3—C4 | 1.376 (9) |
O1—H1 | 0.8200 | C3—H3 | 0.9300 |
O2—H2 | 0.8200 | C4—C5 | 1.362 (9) |
Cl—C4 | 1.732 (6) | C6—C5 | 1.383 (8) |
N—C1 | 1.449 (6) | C6—H6 | 0.9300 |
N—H1N | 0.8900 | C5—H5 | 0.9300 |
N—H2N | 0.8900 | C7—H1C7 | 0.9600 |
N—H3N | 0.8900 | C7—H2C7 | 0.9600 |
C1—C6 | 1.376 (7) | C7—H3C7 | 0.9600 |
O4—P1—O3 | 115.8 (2) | C3—C2—C7 | 120.9 (6) |
O4—P1—O2 | 108.4 (2) | C4—C3—C2 | 120.8 (6) |
O3—P1—O2 | 109.2 (2) | C4—C3—H3 | 119.6 |
O4—P1—O1 | 105.2 (2) | C2—C3—H3 | 119.6 |
O3—P1—O1 | 110.2 (2) | C5—C4—C3 | 121.3 (6) |
O2—P1—O1 | 107.7 (2) | C5—C4—Cl | 118.8 (5) |
P1—O1—H1 | 109.5 | C3—C4—Cl | 119.8 (5) |
P1—O2—H2 | 109.5 | C1—C6—C5 | 120.8 (5) |
C1—N—H1N | 109.5 | C1—C6—H6 | 119.6 |
C1—N—H2N | 109.5 | C5—C6—H6 | 119.6 |
H1N—N—H2N | 109.5 | C4—C5—C6 | 118.5 (6) |
C1—N—H3N | 109.5 | C4—C5—H5 | 120.8 |
H1N—N—H3N | 109.5 | C6—C5—H5 | 120.8 |
H2N—N—H3N | 109.5 | C2—C7—H1C7 | 109.5 |
C6—C1—C2 | 121.2 (5) | C2—C7—H2C7 | 109.5 |
C6—C1—N | 118.5 (5) | H1C7—C7—H2C7 | 109.5 |
C2—C1—N | 120.3 (4) | C2—C7—H3C7 | 109.5 |
C1—C2—C3 | 117.5 (5) | H1C7—C7—H3C7 | 109.5 |
C1—C2—C7 | 121.7 (5) | H2C7—C7—H3C7 | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.86 | 2.611 (4) | 151 |
O2—H2···O3ii | 0.82 | 1.84 | 2.644 (5) | 166 |
N—H1N···O3iii | 0.89 | 2.04 | 2.900 (5) | 162 |
N—H2N···O4iv | 0.89 | 1.82 | 2.704 (5) | 173 |
N—H3N···O4 | 0.89 | 1.88 | 2.722 (5) | 158 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y, −z; (iii) −x+1, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2. |