Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004105/om6083sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004105/om60832sup2.hkl |
CCDC reference: 183790
Key indicators
- Single-crystal X-ray study
- T = 193 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.092
- Data-to-parameter ratio = 16.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_741 Alert C Bond Calc 0.880(15), Rep 0.88000 .... Missing s.u. N -H1N 1.555 1.555 PLAT_745 Alert C D-H Calc 0.880(15), Rep 0.88000 .... Missing s.u. N -H1N 1.555 1.555 PLAT_746 Alert C H...A Calc 2.023(18), Rep 2.02000 .... Missing s.u. H1N -O1 1.555 4.654 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.39 From the CIF: _reflns_number_total 1882 Count of symmetry unique reflns 1038 Completeness (_total/calc) 181.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 844 Fraction of Friedel pairs measured 0.813 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8H14NO2P | Dx = 1.336 Mg m−3 |
Mr = 187.17 | Melting point: 383 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6912 (16) Å | Cell parameters from 3122 reflections |
b = 13.389 (2) Å | θ = 2.6–26.4° |
c = 7.1699 (12) Å | µ = 0.26 mm−1 |
V = 930.3 (3) Å3 | T = 193 K |
Z = 4 | Rod, colorless |
F(000) = 400 | 0.59 × 0.09 × 0.08 mm |
Bruker PLATFORM diffractometer/SMART 1000 CCD detector | 1882 independent reflections |
Radiation source: fine-focus sealed tube | 1600 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 1.5° |
ω scans | h = −12→12 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −16→16 |
Tmin = 0.864, Tmax = 0.980 | l = −8→8 |
5403 measured reflections |
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0448P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1882 reflections | Δρmax = 0.49 e Å−3 |
115 parameters | Δρmin = −0.23 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 844 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (14) |
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. The hydrogen atoms attached to carbons were refined with fixed C—H distances and with isotropic displacement parameters 20% greater than those for their attached atoms. The amino hydrogen H1N was assigned a fixed N—H distance (0.88 Å) but its atomic coordinates and isotropic displacement parameter were otherwise allowed to freely refine. |
x | y | z | Uiso*/Ueq | ||
P | 0.54459 (6) | 0.29565 (4) | 0.32273 (12) | 0.02147 (17) | |
O1 | 0.6080 (2) | 0.29395 (14) | 0.5081 (3) | 0.0299 (5) | |
O2 | 0.40149 (16) | 0.35245 (12) | 0.3267 (3) | 0.0267 (4) | |
N | 0.6323 (2) | 0.35457 (17) | 0.1644 (3) | 0.0248 (5) | |
H1N | 0.7139 (12) | 0.3288 (17) | 0.140 (4) | 0.028 (8)* | |
C1 | 0.5049 (3) | 0.1712 (2) | 0.2506 (4) | 0.0270 (6) | |
H1 | 0.4828 | 0.1229 | 0.3430 | 0.032* | |
C2 | 0.5051 (3) | 0.1443 (2) | 0.0769 (4) | 0.0266 (6) | |
C3 | 0.5084 (3) | 0.1250 (2) | −0.1005 (4) | 0.0264 (6) | |
C4 | 0.6381 (3) | 0.09222 (19) | −0.1965 (5) | 0.0346 (7) | |
H4A | 0.7117 | 0.0839 | −0.1040 | 0.042* | |
H4B | 0.6657 | 0.1428 | −0.2880 | 0.042* | |
H4C | 0.6218 | 0.0285 | −0.2601 | 0.042* | |
C5 | 0.3834 (3) | 0.1376 (2) | −0.2210 (4) | 0.0384 (8) | |
H5A | 0.3033 | 0.1531 | −0.1427 | 0.046* | |
H5B | 0.3662 | 0.0756 | −0.2900 | 0.046* | |
H5C | 0.3988 | 0.1923 | −0.3093 | 0.046* | |
C6 | 0.3385 (3) | 0.3794 (2) | 0.1510 (4) | 0.0332 (7) | |
H6A | 0.2494 | 0.4133 | 0.1740 | 0.040* | |
H6B | 0.3204 | 0.3184 | 0.0768 | 0.040* | |
C7 | 0.4334 (3) | 0.4478 (2) | 0.0445 (4) | 0.0308 (7) | |
H7A | 0.4537 | 0.5077 | 0.1209 | 0.037* | |
H7B | 0.3872 | 0.4702 | −0.0714 | 0.037* | |
C8 | 0.5673 (3) | 0.3953 (2) | −0.0045 (4) | 0.0282 (6) | |
H8A | 0.5485 | 0.3405 | −0.0935 | 0.034* | |
H8B | 0.6310 | 0.4431 | −0.0652 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P | 0.0175 (3) | 0.0286 (3) | 0.0184 (3) | −0.0006 (2) | −0.0009 (4) | 0.0009 (4) |
O1 | 0.0282 (11) | 0.0390 (11) | 0.0225 (11) | −0.0042 (9) | −0.0050 (9) | 0.0030 (10) |
O2 | 0.0212 (8) | 0.0403 (10) | 0.0185 (9) | 0.0033 (7) | 0.0014 (11) | 0.0016 (11) |
N | 0.0197 (12) | 0.0324 (13) | 0.0225 (13) | 0.0018 (10) | 0.0044 (11) | 0.0036 (10) |
C1 | 0.0250 (15) | 0.0307 (14) | 0.0255 (15) | −0.0041 (12) | 0.0004 (12) | 0.0054 (12) |
C2 | 0.0200 (13) | 0.0244 (15) | 0.0353 (17) | −0.0020 (12) | 0.0007 (12) | 0.0008 (12) |
C3 | 0.0270 (16) | 0.0265 (13) | 0.0257 (15) | −0.0067 (13) | 0.0009 (12) | −0.0009 (12) |
C4 | 0.0352 (15) | 0.0368 (14) | 0.0319 (19) | −0.0037 (11) | 0.0060 (15) | −0.0022 (16) |
C5 | 0.0308 (17) | 0.0511 (19) | 0.033 (2) | −0.0058 (14) | −0.0057 (13) | −0.0039 (14) |
C6 | 0.0221 (14) | 0.0496 (17) | 0.0278 (17) | 0.0107 (13) | −0.0035 (13) | 0.0007 (14) |
C7 | 0.0362 (18) | 0.0316 (15) | 0.0246 (17) | 0.0078 (13) | −0.0059 (13) | 0.0030 (12) |
C8 | 0.0317 (16) | 0.0312 (14) | 0.0217 (14) | −0.0012 (11) | 0.0023 (13) | 0.0018 (12) |
P—O1 | 1.464 (2) | C4—H4B | 0.9800 |
P—O2 | 1.5819 (16) | C4—H4C | 0.9800 |
P—N | 1.623 (2) | C5—H5A | 0.9800 |
P—C1 | 1.787 (3) | C5—H5B | 0.9800 |
O2—C6 | 1.445 (3) | C5—H5C | 0.9800 |
N—C8 | 1.470 (4) | C6—C7 | 1.507 (4) |
N—H1N | 0.880 | C6—H6A | 0.9900 |
C1—C2 | 1.296 (4) | C6—H6B | 0.9900 |
C1—H1 | 0.9500 | C7—C8 | 1.517 (4) |
C2—C3 | 1.299 (4) | C7—H7A | 0.9900 |
C3—C4 | 1.498 (4) | C7—H7B | 0.9900 |
C3—C5 | 1.498 (4) | C8—H8A | 0.9900 |
C4—H4A | 0.9800 | C8—H8B | 0.9900 |
O1—P—O2 | 111.06 (12) | C3—C5—H5B | 109.5 |
O1—P—N | 114.98 (12) | C3—C5—H5C | 109.5 |
O1—P—C1 | 109.79 (12) | H5A—C5—H5B | 109.5 |
O2—P—N | 103.77 (11) | H5A—C5—H5C | 109.5 |
O2—P—C1 | 105.35 (11) | H5B—C5—H5C | 109.5 |
N—P—C1 | 111.33 (13) | O2—C6—C7 | 109.6 (2) |
P—O2—C6 | 118.32 (17) | O2—C6—H6A | 109.7 |
P—N—C8 | 122.16 (18) | O2—C6—H6B | 109.7 |
P—N—H1N | 114.7 (17) | C7—C6—H6A | 109.7 |
C8—N—H1N | 111.6 (19) | C7—C6—H6B | 109.7 |
P—C1—C2 | 122.4 (2) | H6A—C6—H6B | 108.2 |
P—C1—H1 | 118.8 | C6—C7—C8 | 110.9 (2) |
C2—C1—H1 | 118.8 | C6—C7—H7A | 109.5 |
C1—C2—C3 | 175.2 (3) | C6—C7—H7B | 109.5 |
C2—C3—C4 | 121.9 (3) | C8—C7—H7A | 109.5 |
C2—C3—C5 | 121.5 (3) | C8—C7—H7B | 109.5 |
C4—C3—C5 | 116.5 (3) | H7A—C7—H7B | 108.0 |
C3—C4—H4A | 109.5 | N—C8—C7 | 110.4 (2) |
C3—C4—H4B | 109.5 | N—C8—H8A | 109.6 |
C3—C4—H4C | 109.5 | N—C8—H8B | 109.6 |
H4A—C4—H4B | 109.5 | C7—C8—H8A | 109.6 |
H4A—C4—H4C | 109.5 | C7—C8—H8B | 109.6 |
H4B—C4—H4C | 109.5 | H8A—C8—H8B | 108.1 |
C3—C5—H5A | 109.5 | ||
O1—P—O2—C6 | 167.35 (18) | O2—P—C1—C2 | 90.7 (3) |
N—P—O2—C6 | 43.3 (2) | N—P—C1—C2 | −21.2 (3) |
C1—P—O2—C6 | −73.8 (2) | P—O2—C6—C7 | −60.3 (3) |
O1—P—N—C8 | −157.4 (2) | P—N—C8—C7 | 44.1 (3) |
O2—P—N—C8 | −35.9 (2) | O2—C6—C7—C8 | 63.3 (3) |
C1—P—N—C8 | 76.9 (2) | C6—C7—C8—N | −54.7 (3) |
O1—P—C1—C2 | −149.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1N···O1i | 0.88 | 2.02 | 2.872 (3) | 162 |
Symmetry code: (i) −x+3/2, y, z−1/2. |
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