Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000090/tk6046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000090/tk6046Isup2.hkl |
CCDC reference: 180780
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.016 Å
- R factor = 0.063
- wR factor = 0.184
- Data-to-parameter ratio = 9.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2439 Count of symmetry unique reflns 2001 Completeness (_total/calc) 121.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 438 Fraction of Friedel pairs measured 0.219 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C9H11NO2·C9H12NO2+·H2PO4− | F(000) = 452 |
Mr = 428.37 | Dx = 1.414 Mg m−3 Dm = 1.41 Mg m−3 Dm measured by flotation using a mixture of carbon tetrachloride and xylene |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 13.441 (1) Å | θ = 8.5–13.9° |
b = 4.8760 (4) Å | µ = 0.19 mm−1 |
c = 15.470 (2) Å | T = 293 K |
β = 97.12 (1)° | Needle, colorless |
V = 1006.06 (17) Å3 | 0.6 × 0.13 × 0.10 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | 1167 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.064 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
ω–2θ scans | h = −1→15 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→5 |
Tmin = 0.972, Tmax = 0.982 | l = −18→18 |
2762 measured reflections | 3 standard reflections every 60 min |
2439 independent reflections | intensity decay: none |
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)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.184 | w = 1/[σ2(Fo2) + (0.0874P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
2439 reflections | Δρmax = 0.31 e Å−3 |
267 parameters | Δρmin = −0.34 e Å−3 |
49 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (4) |
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 | 0.77004 (17) | 0.1971 (6) | 0.45109 (16) | 0.0295 (7) | |
O1 | 0.8746 (4) | 0.2720 (13) | 0.4371 (4) | 0.0324 (18) | |
O3 | 0.7658 (4) | 0.0876 (16) | 0.5437 (4) | 0.0406 (19) | |
H3 | 0.8009 | −0.0499 | 0.5515 | 0.061* | |
O2 | 0.6962 (4) | 0.4365 (15) | 0.4406 (4) | 0.0374 (19) | |
O4 | 0.7345 (5) | −0.0360 (15) | 0.3853 (4) | 0.041 (2) | |
H4 | 0.6771 | −0.0809 | 0.3916 | 0.061* | |
O1A | 1.1033 (4) | 1.2209 (16) | 0.4150 (4) | 0.0377 (17) | |
O1B | 1.1757 (4) | 1.1159 (16) | 0.2984 (4) | 0.041 (2) | |
C11 | 1.1129 (6) | 1.086 (2) | 0.3489 (6) | 0.030 (2) | |
C12 | 1.0363 (7) | 0.850 (2) | 0.3259 (5) | 0.032 (3) | |
H12 | 1.0723 | 0.6850 | 0.3116 | 0.038* | |
N11 | 0.9841 (5) | 0.7951 (16) | 0.4034 (4) | 0.028 (2) | |
H11A | 0.9407 | 0.6584 | 0.3917 | 0.041* | |
H11B | 0.9515 | 0.9451 | 0.4168 | 0.041* | |
H11C | 1.0290 | 0.7489 | 0.4483 | 0.041* | |
C13 | 0.9623 (7) | 0.932 (2) | 0.2478 (6) | 0.041 (3) | |
H13A | 0.9136 | 1.0565 | 0.2677 | 0.050* | |
H13B | 0.9985 | 1.0337 | 0.2077 | 0.050* | |
C14 | 0.9068 (6) | 0.705 (2) | 0.1986 (6) | 0.033 (2) | |
C15 | 0.8178 (8) | 0.615 (3) | 0.2212 (8) | 0.059 (4) | |
H15 | 0.7938 | 0.6952 | 0.2691 | 0.071* | |
C16 | 0.7613 (10) | 0.412 (3) | 0.1772 (9) | 0.079 (4) | |
H16 | 0.7026 | 0.3479 | 0.1964 | 0.095* | |
C17 | 0.7938 (13) | 0.310 (3) | 0.1064 (9) | 0.086 (5) | |
H17 | 0.7540 | 0.1806 | 0.0746 | 0.104* | |
C18 | 0.8835 (13) | 0.385 (3) | 0.0763 (7) | 0.083 (5) | |
H18 | 0.9059 | 0.3043 | 0.0278 | 0.100* | |
C19 | 0.9380 (10) | 0.593 (3) | 0.1260 (7) | 0.070 (4) | |
H19 | 0.9975 | 0.6562 | 0.1081 | 0.084* | |
O2A | 0.5386 (4) | 0.8742 (15) | 0.4462 (4) | 0.041 (2) | |
O2B | 0.5193 (5) | 0.5003 (15) | 0.3635 (4) | 0.0336 (19) | |
H2B | 0.578 (8) | 0.47 (3) | 0.392 (6) | 0.06 (4)* | |
C21 | 0.4904 (6) | 0.738 (3) | 0.3897 (6) | 0.028 (3) | |
C22 | 0.3946 (6) | 0.841 (2) | 0.3424 (5) | 0.025 (2) | |
H22 | 0.3437 | 0.6961 | 0.3401 | 0.030* | |
N21 | 0.3623 (5) | 1.0778 (17) | 0.3910 (5) | 0.032 (2) | |
H21A | 0.3045 | 1.1418 | 0.3643 | 0.049* | |
H21B | 0.4087 | 1.2088 | 0.3932 | 0.049* | |
H21C | 0.3542 | 1.0261 | 0.4449 | 0.049* | |
C23 | 0.4090 (7) | 0.927 (2) | 0.2500 (5) | 0.035 (3) | |
H23A | 0.3633 | 1.0771 | 0.2326 | 0.042* | |
H23B | 0.4767 | 0.9963 | 0.2503 | 0.042* | |
C24 | 0.3918 (7) | 0.703 (3) | 0.1831 (5) | 0.035 (2) | |
C25 | 0.2988 (8) | 0.601 (3) | 0.1599 (7) | 0.056 (4) | |
H25 | 0.2457 | 0.6704 | 0.1864 | 0.068* | |
C26 | 0.2799 (11) | 0.396 (3) | 0.0977 (8) | 0.071 (4) | |
H26 | 0.2155 | 0.3268 | 0.0837 | 0.086* | |
C27 | 0.3567 (14) | 0.300 (3) | 0.0577 (8) | 0.076 (4) | |
H27 | 0.3450 | 0.1644 | 0.0154 | 0.091* | |
C28 | 0.4515 (12) | 0.400 (3) | 0.0793 (7) | 0.068 (4) | |
H28 | 0.5045 | 0.3319 | 0.0525 | 0.081* | |
C29 | 0.4675 (9) | 0.605 (3) | 0.1413 (7) | 0.055 (3) | |
H29 | 0.5316 | 0.6767 | 0.1548 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0208 (12) | 0.0254 (16) | 0.0424 (14) | 0.0070 (16) | 0.0049 (10) | −0.0021 (16) |
O1 | 0.019 (3) | 0.015 (5) | 0.065 (4) | 0.001 (3) | 0.013 (3) | 0.004 (3) |
O3 | 0.030 (4) | 0.034 (5) | 0.058 (4) | 0.021 (4) | 0.008 (3) | −0.003 (4) |
O2 | 0.022 (3) | 0.030 (5) | 0.059 (4) | 0.016 (4) | −0.001 (3) | −0.002 (4) |
O4 | 0.039 (4) | 0.034 (5) | 0.051 (4) | −0.007 (4) | 0.013 (3) | −0.013 (4) |
O1A | 0.029 (3) | 0.028 (5) | 0.057 (4) | −0.013 (4) | 0.010 (3) | −0.015 (4) |
O1B | 0.028 (3) | 0.047 (6) | 0.050 (4) | −0.008 (4) | 0.009 (3) | 0.003 (4) |
C11 | 0.026 (5) | 0.023 (6) | 0.038 (5) | 0.001 (5) | −0.003 (5) | 0.010 (5) |
C12 | 0.029 (5) | 0.027 (7) | 0.038 (5) | −0.003 (5) | 0.004 (4) | −0.008 (5) |
N11 | 0.017 (3) | 0.011 (5) | 0.052 (4) | −0.002 (4) | −0.006 (3) | −0.004 (4) |
C13 | 0.044 (6) | 0.023 (7) | 0.054 (6) | 0.000 (6) | −0.008 (5) | 0.008 (6) |
C14 | 0.037 (5) | 0.016 (6) | 0.042 (5) | 0.006 (7) | −0.006 (4) | 0.002 (6) |
C15 | 0.047 (7) | 0.039 (9) | 0.085 (8) | 0.005 (7) | −0.016 (6) | −0.019 (7) |
C16 | 0.057 (8) | 0.070 (11) | 0.097 (9) | −0.006 (8) | −0.039 (8) | −0.013 (10) |
C17 | 0.123 (12) | 0.053 (10) | 0.067 (9) | −0.014 (10) | −0.055 (9) | 0.004 (8) |
C18 | 0.146 (14) | 0.058 (11) | 0.040 (7) | 0.026 (11) | −0.007 (9) | −0.019 (8) |
C19 | 0.101 (9) | 0.064 (10) | 0.044 (6) | 0.011 (9) | 0.009 (6) | −0.008 (7) |
O2A | 0.027 (4) | 0.022 (5) | 0.069 (4) | 0.006 (4) | −0.011 (3) | 0.003 (4) |
O2B | 0.022 (4) | 0.024 (5) | 0.054 (4) | 0.007 (4) | 0.003 (3) | −0.006 (4) |
C21 | 0.015 (4) | 0.029 (8) | 0.038 (5) | −0.015 (6) | −0.001 (4) | −0.004 (6) |
C22 | 0.022 (5) | 0.012 (6) | 0.042 (5) | 0.003 (5) | 0.006 (4) | −0.012 (5) |
N21 | 0.022 (4) | 0.023 (5) | 0.052 (5) | 0.000 (4) | 0.003 (4) | 0.008 (4) |
C23 | 0.044 (6) | 0.027 (7) | 0.033 (5) | 0.003 (6) | 0.003 (5) | 0.014 (5) |
C24 | 0.048 (6) | 0.025 (6) | 0.031 (5) | −0.003 (7) | 0.004 (4) | 0.000 (6) |
C25 | 0.056 (7) | 0.050 (9) | 0.057 (7) | 0.018 (7) | −0.016 (6) | 0.000 (7) |
C26 | 0.085 (10) | 0.050 (10) | 0.071 (8) | −0.013 (9) | −0.024 (8) | −0.003 (8) |
C27 | 0.152 (13) | 0.022 (8) | 0.047 (7) | 0.011 (9) | −0.010 (9) | −0.003 (6) |
C28 | 0.108 (11) | 0.041 (9) | 0.061 (8) | 0.016 (9) | 0.037 (8) | 0.000 (8) |
C29 | 0.073 (8) | 0.031 (8) | 0.065 (7) | 0.002 (7) | 0.024 (6) | −0.009 (7) |
P1—O1 | 1.494 (5) | C18—H18 | 0.9300 |
P1—O2 | 1.528 (7) | C19—H19 | 0.9300 |
P1—O3 | 1.537 (7) | O2A—C21 | 1.217 (10) |
P1—O4 | 1.560 (7) | O2B—C21 | 1.305 (13) |
O3—H3 | 0.8200 | O2B—H2B | 0.87 (10) |
O4—H4 | 0.8200 | C21—C22 | 1.486 (11) |
O1A—C11 | 1.235 (11) | C22—N21 | 1.474 (11) |
O1B—C11 | 1.228 (10) | C22—C23 | 1.526 (11) |
C11—C12 | 1.556 (14) | C22—H22 | 0.9800 |
C12—N11 | 1.487 (10) | N21—H21A | 0.8900 |
C12—C13 | 1.520 (12) | N21—H21B | 0.8900 |
C12—H12 | 0.9800 | N21—H21C | 0.8900 |
N11—H11A | 0.8900 | C23—C24 | 1.504 (14) |
N11—H11B | 0.8900 | C23—H23A | 0.9700 |
N11—H11C | 0.8900 | C23—H23B | 0.9700 |
C13—C14 | 1.493 (13) | C24—C25 | 1.352 (13) |
C13—H13A | 0.9700 | C24—C29 | 1.358 (13) |
C13—H13B | 0.9700 | C25—C26 | 1.387 (17) |
C14—C19 | 1.358 (14) | C25—H25 | 0.9300 |
C14—C15 | 1.360 (13) | C26—C27 | 1.351 (17) |
C15—C16 | 1.377 (17) | C26—H26 | 0.9300 |
C15—H15 | 0.9300 | C27—C28 | 1.367 (18) |
C16—C17 | 1.323 (17) | C27—H27 | 0.9300 |
C16—H16 | 0.9300 | C28—C29 | 1.381 (16) |
C17—C18 | 1.392 (18) | C28—H28 | 0.9300 |
C17—H17 | 0.9300 | C29—H29 | 0.9300 |
C18—C19 | 1.423 (18) | ||
O1—P1—O2 | 114.1 (4) | C14—C19—C18 | 122.7 (13) |
O1—P1—O3 | 111.4 (3) | C14—C19—H19 | 118.6 |
O2—P1—O3 | 105.4 (4) | C18—C19—H19 | 118.6 |
O1—P1—O4 | 107.5 (4) | C21—O2B—H2B | 107 (8) |
O2—P1—O4 | 110.2 (4) | O2A—C21—O2B | 123.7 (9) |
O3—P1—O4 | 108.1 (4) | O2A—C21—C22 | 121.5 (10) |
P1—O3—H3 | 109.5 | O2B—C21—C22 | 114.8 (8) |
P1—O4—H4 | 109.5 | N21—C22—C21 | 107.7 (7) |
O1B—C11—O1A | 128.0 (10) | N21—C22—C23 | 109.9 (8) |
O1B—C11—C12 | 115.4 (9) | C21—C22—C23 | 110.6 (7) |
O1A—C11—C12 | 116.6 (8) | N21—C22—H22 | 109.5 |
N11—C12—C13 | 111.2 (7) | C21—C22—H22 | 109.5 |
N11—C12—C11 | 108.3 (7) | C23—C22—H22 | 109.5 |
C13—C12—C11 | 109.6 (8) | C22—N21—H21A | 109.5 |
N11—C12—H12 | 109.2 | C22—N21—H21B | 109.5 |
C13—C12—H12 | 109.2 | H21A—N21—H21B | 109.5 |
C11—C12—H12 | 109.2 | C22—N21—H21C | 109.5 |
C12—N11—H11A | 109.5 | H21A—N21—H21C | 109.5 |
C12—N11—H11B | 109.5 | H21B—N21—H21C | 109.5 |
H11A—N11—H11B | 109.5 | C24—C23—C22 | 114.6 (9) |
C12—N11—H11C | 109.5 | C24—C23—H23A | 108.6 |
H11A—N11—H11C | 109.5 | C22—C23—H23A | 108.6 |
H11B—N11—H11C | 109.5 | C24—C23—H23B | 108.6 |
C14—C13—C12 | 116.5 (9) | C22—C23—H23B | 108.6 |
C14—C13—H13A | 108.2 | H23A—C23—H23B | 107.6 |
C12—C13—H13A | 108.2 | C25—C24—C29 | 117.8 (11) |
C14—C13—H13B | 108.2 | C25—C24—C23 | 120.5 (9) |
C12—C13—H13B | 108.2 | C29—C24—C23 | 121.6 (9) |
H13A—C13—H13B | 107.3 | C24—C25—C26 | 122.1 (12) |
C19—C14—C15 | 117.2 (11) | C24—C25—H25 | 118.9 |
C19—C14—C13 | 122.1 (10) | C26—C25—H25 | 118.9 |
C15—C14—C13 | 120.5 (10) | C27—C26—C25 | 118.9 (13) |
C14—C15—C16 | 123.5 (12) | C27—C26—H26 | 120.6 |
C14—C15—H15 | 118.2 | C25—C26—H26 | 120.6 |
C16—C15—H15 | 118.2 | C26—C27—C28 | 120.4 (13) |
C17—C16—C15 | 117.3 (14) | C26—C27—H27 | 119.8 |
C17—C16—H16 | 121.3 | C28—C27—H27 | 119.8 |
C15—C16—H16 | 121.3 | C27—C28—C29 | 119.2 (12) |
C16—C17—C18 | 124.6 (14) | C27—C28—H28 | 120.4 |
C16—C17—H17 | 117.7 | C29—C28—H28 | 120.4 |
C18—C17—H17 | 117.7 | C24—C29—C28 | 121.5 (12) |
C17—C18—C19 | 114.5 (12) | C24—C29—H29 | 119.2 |
C17—C18—H18 | 122.8 | C28—C29—H29 | 119.2 |
C19—C18—H18 | 122.8 | ||
O1B—C11—C12—N11 | 165.4 (8) | O2A—C21—C22—N21 | −14.1 (11) |
O1A—C11—C12—N11 | −14.7 (11) | O2B—C21—C22—N21 | 168.4 (8) |
O1B—C11—C12—C13 | −73.1 (11) | O2A—C21—C22—C23 | 106.0 (10) |
O1A—C11—C12—C13 | 106.8 (10) | O2B—C21—C22—C23 | −71.5 (11) |
N11—C12—C13—C14 | −80.3 (11) | N21—C22—C23—C24 | −151.4 (8) |
C11—C12—C13—C14 | 159.9 (9) | C21—C22—C23—C24 | 89.8 (10) |
C12—C13—C14—C19 | −95.8 (12) | C22—C23—C24—C25 | 68.7 (13) |
C12—C13—C14—C15 | 89.5 (12) | C22—C23—C24—C29 | −114.4 (11) |
C19—C14—C15—C16 | 3.0 (18) | C29—C24—C25—C26 | 2.2 (18) |
C13—C14—C15—C16 | 178.0 (10) | C23—C24—C25—C26 | 179.2 (10) |
C14—C15—C16—C17 | −4 (2) | C24—C25—C26—C27 | −1.4 (19) |
C15—C16—C17—C18 | 4 (2) | C25—C26—C27—C28 | 1 (2) |
C16—C17—C18—C19 | −3 (2) | C26—C27—C28—C29 | −1 (2) |
C15—C14—C19—C18 | −2.3 (17) | C25—C24—C29—C28 | −2.4 (17) |
C13—C14—C19—C18 | −177.1 (10) | C23—C24—C29—C28 | −179.3 (10) |
C17—C18—C19—C14 | 2.1 (19) | C27—C28—C29—C24 | 1.8 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1Ai | 0.82 | 1.74 | 2.535 (9) | 164 |
O4—H4···O2Aii | 0.82 | 2.15 | 2.938 (9) | 162 |
N11—H11A···O1 | 0.89 | 2.23 | 3.022 (10) | 148 |
N11—H11B···O1iii | 0.89 | 1.95 | 2.834 (10) | 176 |
N11—H11C···O1iv | 0.89 | 2.07 | 2.923 (8) | 161 |
O2B—H2B···O2 | 0.87 (10) | 1.68 (10) | 2.543 (9) | 172 (12) |
N21—H21A···O1Bv | 0.89 | 1.90 | 2.736 (9) | 156 |
N21—H21B···O2Biii | 0.89 | 2.15 | 3.017 (10) | 165 |
N21—H21B···O2Avi | 0.89 | 2.62 | 3.062 (9) | 111 |
N21—H21C···O2vi | 0.89 | 2.02 | 2.896 (9) | 167 |
Symmetry codes: (i) −x+2, y−3/2, −z+1; (ii) x, y−1, z; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+1; (v) x−1, y, z; (vi) −x+1, y+1/2, −z+1. |