Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020732/su6134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020732/su6134Isup2.hkl |
CCDC reference: 251759
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.087
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O1 .. C14 .. 2.85 Ang.
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 2233 Count of symmetry unique reflns 2279 Completeness (_total/calc) 97.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C18H12N3O7P | F(000) = 848 |
Mr = 413.28 | Dx = 1.555 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 2409 reflections |
a = 19.1402 (9) Å | θ = 2.5–28.3° |
b = 5.4608 (2) Å | µ = 0.21 mm−1 |
c = 16.8888 (7) Å | T = 105 K |
V = 1765.23 (13) Å3 | Needle, colorless |
Z = 4 | 0.45 × 0.05 × 0.05 mm |
KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer | 2233 independent reflections |
Radiation source: fine-focus sealed tube | 1731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
ω scans with κ offsets | θmax = 28.3°, θmin = 3.2° |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | h = −25→25 |
Tmin = 0.896, Tmax = 0.990 | k = −7→7 |
12164 measured reflections | l = −22→22 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0336P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2233 reflections | Δρmax = 0.29 e Å−3 |
263 parameters | Δρmin = −0.41 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0052 (11) |
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 | 0.79288 (4) | 0.73595 (15) | 0.61513 (7) | 0.0136 (2) | |
O1 | 0.79709 (12) | 1.0072 (4) | 0.60987 (19) | 0.0189 (5) | |
O2 | 0.55803 (14) | 1.0206 (5) | 0.74225 (17) | 0.0274 (7) | |
O3 | 0.47919 (12) | 0.7426 (5) | 0.72288 (18) | 0.0269 (6) | |
O4 | 0.74673 (15) | 0.0293 (5) | 0.82389 (18) | 0.0261 (6) | |
O5 | 0.81876 (15) | 0.0729 (5) | 0.92162 (17) | 0.0285 (7) | |
O6 | 0.97054 (14) | 0.0028 (5) | 0.56494 (18) | 0.0265 (6) | |
O7 | 0.98516 (16) | −0.0385 (5) | 0.4384 (2) | 0.0343 (7) | |
N1 | 0.53813 (15) | 0.8245 (5) | 0.7136 (2) | 0.0205 (7) | |
N2 | 0.79523 (17) | 0.1349 (5) | 0.8572 (2) | 0.0206 (7) | |
N3 | 0.95912 (15) | 0.0642 (5) | 0.4957 (2) | 0.0198 (7) | |
C1 | 0.70323 (16) | 0.6291 (6) | 0.6153 (3) | 0.0143 (6) | |
C2 | 0.65604 (17) | 0.7648 (7) | 0.6604 (2) | 0.0155 (7) | |
H2 | 0.6706 | 0.9084 | 0.6876 | 0.019* | |
C3 | 0.58770 (18) | 0.6854 (6) | 0.6645 (2) | 0.0153 (8) | |
C4 | 0.56390 (17) | 0.4785 (6) | 0.6246 (3) | 0.0189 (8) | |
H4 | 0.5165 | 0.4282 | 0.6285 | 0.023* | |
C5 | 0.61127 (18) | 0.3479 (6) | 0.5791 (2) | 0.0180 (8) | |
H5 | 0.5961 | 0.2073 | 0.5508 | 0.022* | |
C6 | 0.68047 (18) | 0.4200 (6) | 0.5743 (2) | 0.0156 (7) | |
H6 | 0.7126 | 0.3281 | 0.5434 | 0.019* | |
C7 | 0.82896 (18) | 0.6206 (6) | 0.7069 (2) | 0.0143 (8) | |
C8 | 0.80087 (18) | 0.4157 (6) | 0.7441 (2) | 0.0146 (7) | |
H8 | 0.7647 | 0.3238 | 0.7197 | 0.017* | |
C9 | 0.82680 (18) | 0.3490 (6) | 0.8172 (2) | 0.0164 (8) | |
C10 | 0.88027 (19) | 0.4751 (7) | 0.8542 (2) | 0.0201 (8) | |
H10 | 0.8978 | 0.4226 | 0.9040 | 0.024* | |
C11 | 0.9077 (2) | 0.6798 (7) | 0.8169 (3) | 0.0245 (9) | |
H11 | 0.9440 | 0.7709 | 0.8416 | 0.029* | |
C12 | 0.88212 (17) | 0.7513 (6) | 0.7436 (2) | 0.0174 (8) | |
H12 | 0.9012 | 0.8915 | 0.7182 | 0.021* | |
C13 | 0.83592 (18) | 0.5791 (6) | 0.5346 (2) | 0.0152 (8) | |
C14 | 0.88292 (17) | 0.3876 (6) | 0.5477 (2) | 0.0145 (8) | |
H14 | 0.8945 | 0.3372 | 0.5999 | 0.017* | |
C15 | 0.91210 (17) | 0.2735 (6) | 0.4825 (2) | 0.0155 (7) | |
C16 | 0.89710 (19) | 0.3411 (7) | 0.4054 (2) | 0.0217 (9) | |
H16 | 0.9178 | 0.2577 | 0.3620 | 0.026* | |
C17 | 0.8509 (2) | 0.5346 (7) | 0.3930 (3) | 0.0232 (9) | |
H17 | 0.8399 | 0.5852 | 0.3406 | 0.028* | |
C18 | 0.82085 (19) | 0.6532 (7) | 0.4573 (2) | 0.0192 (8) | |
H18 | 0.7898 | 0.7860 | 0.4486 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0124 (3) | 0.0137 (4) | 0.0148 (4) | −0.0005 (3) | 0.0008 (4) | 0.0001 (4) |
O1 | 0.0191 (11) | 0.0133 (10) | 0.0243 (14) | −0.0028 (10) | 0.0004 (12) | 0.0002 (14) |
O2 | 0.0262 (15) | 0.0293 (15) | 0.0267 (17) | −0.0008 (12) | 0.0032 (13) | −0.0121 (14) |
O3 | 0.0160 (13) | 0.0282 (14) | 0.0366 (18) | −0.0004 (11) | 0.0069 (13) | 0.0003 (14) |
O4 | 0.0289 (15) | 0.0279 (13) | 0.0215 (15) | −0.0118 (13) | −0.0005 (13) | 0.0035 (14) |
O5 | 0.0409 (17) | 0.0290 (15) | 0.0156 (16) | −0.0025 (12) | −0.0029 (13) | 0.0052 (13) |
O6 | 0.0308 (15) | 0.0269 (14) | 0.0217 (15) | 0.0098 (12) | −0.0027 (14) | 0.0009 (14) |
O7 | 0.0391 (17) | 0.0316 (16) | 0.0323 (18) | 0.0147 (13) | 0.0143 (15) | −0.0056 (14) |
N1 | 0.0175 (16) | 0.0234 (17) | 0.0205 (18) | 0.0017 (13) | 0.0028 (15) | 0.0018 (14) |
N2 | 0.0261 (17) | 0.0216 (16) | 0.0142 (18) | 0.0006 (14) | 0.0064 (16) | −0.0003 (14) |
N3 | 0.0162 (15) | 0.0181 (15) | 0.025 (2) | 0.0005 (12) | 0.0027 (15) | 0.0006 (15) |
C1 | 0.0110 (14) | 0.0167 (14) | 0.0153 (17) | 0.0016 (13) | −0.0003 (17) | 0.0044 (18) |
C2 | 0.0169 (16) | 0.0172 (16) | 0.0124 (19) | 0.0011 (15) | −0.0030 (15) | −0.0009 (16) |
C3 | 0.0163 (17) | 0.0164 (18) | 0.0133 (19) | 0.0042 (13) | 0.0009 (16) | 0.0009 (15) |
C4 | 0.0118 (16) | 0.0212 (17) | 0.024 (2) | −0.0012 (13) | −0.0009 (17) | 0.0062 (18) |
C5 | 0.0191 (18) | 0.0155 (16) | 0.020 (2) | −0.0017 (14) | −0.0050 (17) | 0.0006 (16) |
C6 | 0.0198 (17) | 0.0119 (16) | 0.0151 (19) | 0.0034 (14) | 0.0038 (17) | −0.0005 (15) |
C7 | 0.0122 (16) | 0.0177 (18) | 0.013 (2) | 0.0037 (13) | −0.0002 (15) | −0.0031 (16) |
C8 | 0.0138 (16) | 0.0164 (17) | 0.0135 (19) | −0.0016 (14) | 0.0022 (16) | −0.0040 (15) |
C9 | 0.0168 (18) | 0.0181 (17) | 0.014 (2) | 0.0019 (14) | 0.0041 (16) | 0.0006 (16) |
C10 | 0.0194 (18) | 0.028 (2) | 0.0131 (19) | 0.0008 (16) | −0.0026 (17) | −0.0016 (17) |
C11 | 0.024 (2) | 0.027 (2) | 0.023 (2) | −0.0054 (15) | −0.0059 (19) | −0.0044 (17) |
C12 | 0.0149 (16) | 0.0165 (17) | 0.021 (2) | −0.0033 (15) | 0.0040 (16) | −0.0025 (17) |
C13 | 0.0121 (17) | 0.0174 (18) | 0.016 (2) | −0.0043 (14) | −0.0011 (16) | 0.0016 (16) |
C14 | 0.0130 (16) | 0.0140 (17) | 0.017 (2) | −0.0006 (14) | 0.0012 (15) | 0.0041 (14) |
C15 | 0.0129 (15) | 0.0157 (16) | 0.018 (2) | 0.0000 (14) | 0.0010 (15) | 0.0014 (16) |
C16 | 0.020 (2) | 0.0267 (19) | 0.018 (2) | 0.0015 (15) | 0.0049 (17) | −0.0044 (17) |
C17 | 0.023 (2) | 0.031 (2) | 0.016 (2) | −0.0013 (17) | 0.0004 (17) | 0.0050 (18) |
C18 | 0.0188 (18) | 0.0214 (19) | 0.017 (2) | 0.0036 (16) | 0.0000 (16) | 0.0033 (17) |
P1—O1 | 1.486 (2) | C6—H6 | 0.9500 |
P1—C1 | 1.812 (3) | C7—C12 | 1.389 (5) |
P1—C7 | 1.810 (4) | C7—C8 | 1.391 (5) |
P1—C13 | 1.806 (4) | C8—C9 | 1.380 (5) |
O2—N1 | 1.235 (4) | C8—H8 | 0.9500 |
O3—N1 | 1.224 (4) | C9—C10 | 1.382 (5) |
O4—N2 | 1.229 (4) | C10—C11 | 1.386 (6) |
O5—N2 | 1.225 (4) | C10—H10 | 0.9500 |
O6—N3 | 1.236 (4) | C11—C12 | 1.388 (6) |
O7—N3 | 1.225 (4) | C11—H11 | 0.9500 |
N1—C3 | 1.471 (5) | C12—H12 | 0.9500 |
N2—C9 | 1.479 (5) | C13—C14 | 1.397 (5) |
N3—C15 | 1.471 (4) | C13—C18 | 1.398 (5) |
C1—C2 | 1.395 (5) | C14—C15 | 1.383 (5) |
C1—C6 | 1.404 (5) | C14—H14 | 0.9500 |
C2—C3 | 1.380 (5) | C15—C16 | 1.384 (6) |
C2—H2 | 0.9500 | C16—C17 | 1.394 (5) |
C3—C4 | 1.392 (5) | C16—H16 | 0.9500 |
C4—C5 | 1.387 (5) | C17—C18 | 1.388 (6) |
C4—H4 | 0.9500 | C17—H17 | 0.9500 |
C5—C6 | 1.384 (5) | C18—H18 | 0.9500 |
C5—H5 | 0.9500 | ||
O1—P1—C13 | 113.76 (18) | C8—C7—P1 | 121.3 (3) |
O1—P1—C7 | 112.17 (17) | C9—C8—C7 | 118.5 (3) |
C13—P1—C7 | 107.80 (16) | C9—C8—H8 | 120.7 |
O1—P1—C1 | 111.87 (14) | C7—C8—H8 | 120.7 |
C13—P1—C1 | 106.27 (18) | C8—C9—C10 | 122.6 (3) |
C7—P1—C1 | 104.36 (18) | C8—C9—N2 | 118.1 (3) |
O3—N1—O2 | 123.5 (3) | C10—C9—N2 | 119.4 (3) |
O3—N1—C3 | 118.5 (3) | C9—C10—C11 | 118.6 (4) |
O2—N1—C3 | 118.0 (3) | C9—C10—H10 | 120.7 |
O5—N2—O4 | 123.7 (3) | C11—C10—H10 | 120.7 |
O5—N2—C9 | 118.3 (3) | C10—C11—C12 | 119.8 (4) |
O4—N2—C9 | 118.1 (3) | C10—C11—H11 | 120.1 |
O7—N3—O6 | 123.5 (3) | C12—C11—H11 | 120.1 |
O7—N3—C15 | 119.0 (3) | C11—C12—C7 | 120.8 (4) |
O6—N3—C15 | 117.5 (3) | C11—C12—H12 | 119.6 |
C2—C1—C6 | 120.0 (3) | C7—C12—H12 | 119.6 |
C2—C1—P1 | 116.3 (3) | C14—C13—C18 | 119.8 (3) |
C6—C1—P1 | 123.7 (3) | C14—C13—P1 | 122.0 (3) |
C3—C2—C1 | 118.3 (3) | C18—C13—P1 | 118.2 (3) |
C3—C2—H2 | 120.8 | C15—C14—C13 | 118.1 (3) |
C1—C2—H2 | 120.8 | C15—C14—H14 | 120.9 |
C2—C3—C4 | 122.7 (3) | C13—C14—H14 | 120.9 |
C2—C3—N1 | 118.5 (3) | C14—C15—C16 | 123.0 (3) |
C4—C3—N1 | 118.7 (3) | C14—C15—N3 | 118.5 (3) |
C5—C4—C3 | 118.2 (3) | C16—C15—N3 | 118.5 (3) |
C5—C4—H4 | 120.9 | C15—C16—C17 | 118.4 (4) |
C3—C4—H4 | 120.9 | C15—C16—H16 | 120.8 |
C6—C5—C4 | 120.8 (3) | C17—C16—H16 | 120.8 |
C6—C5—H5 | 119.6 | C18—C17—C16 | 119.9 (4) |
C4—C5—H5 | 119.6 | C18—C17—H17 | 120.1 |
C5—C6—C1 | 120.0 (3) | C16—C17—H17 | 120.1 |
C5—C6—H6 | 120.0 | C17—C18—C13 | 120.7 (3) |
C1—C6—H6 | 120.0 | C17—C18—H18 | 119.6 |
C12—C7—C8 | 119.7 (4) | C13—C18—H18 | 119.6 |
C12—C7—P1 | 118.9 (3) | ||
O1—P1—C1—C2 | −41.1 (4) | O5—N2—C9—C8 | 179.0 (3) |
C13—P1—C1—C2 | −165.9 (3) | O4—N2—C9—C8 | −1.1 (5) |
C7—P1—C1—C2 | 80.4 (3) | O5—N2—C9—C10 | −1.5 (5) |
O1—P1—C1—C6 | 140.0 (3) | O4—N2—C9—C10 | 178.4 (3) |
C13—P1—C1—C6 | 15.3 (4) | C8—C9—C10—C11 | 1.5 (6) |
C7—P1—C1—C6 | −98.5 (4) | N2—C9—C10—C11 | −178.0 (3) |
C6—C1—C2—C3 | 1.2 (6) | C9—C10—C11—C12 | −1.0 (6) |
P1—C1—C2—C3 | −177.7 (3) | C10—C11—C12—C7 | 0.2 (6) |
C1—C2—C3—C4 | −1.1 (6) | C8—C7—C12—C11 | 0.1 (5) |
C1—C2—C3—N1 | 178.5 (3) | P1—C7—C12—C11 | 175.2 (3) |
O3—N1—C3—C2 | −173.7 (3) | O1—P1—C13—C14 | 130.8 (3) |
O2—N1—C3—C2 | 7.5 (5) | C7—P1—C13—C14 | 5.7 (3) |
O3—N1—C3—C4 | 5.8 (5) | C1—P1—C13—C14 | −105.7 (3) |
O2—N1—C3—C4 | −172.9 (3) | O1—P1—C13—C18 | −49.5 (3) |
C2—C3—C4—C5 | 0.1 (6) | C7—P1—C13—C18 | −174.6 (3) |
N1—C3—C4—C5 | −179.5 (3) | C1—P1—C13—C18 | 74.0 (3) |
C3—C4—C5—C6 | 0.8 (6) | C18—C13—C14—C15 | −1.3 (5) |
C4—C5—C6—C1 | −0.7 (6) | P1—C13—C14—C15 | 178.3 (3) |
C2—C1—C6—C5 | −0.4 (6) | C13—C14—C15—C16 | 0.3 (5) |
P1—C1—C6—C5 | 178.5 (3) | C13—C14—C15—N3 | −177.2 (3) |
O1—P1—C7—C12 | −29.2 (3) | O7—N3—C15—C14 | 179.9 (3) |
C13—P1—C7—C12 | 96.7 (3) | O6—N3—C15—C14 | −0.6 (5) |
C1—P1—C7—C12 | −150.5 (3) | O7—N3—C15—C16 | 2.2 (5) |
O1—P1—C7—C8 | 145.7 (3) | O6—N3—C15—C16 | −178.3 (3) |
C13—P1—C7—C8 | −88.3 (3) | C14—C15—C16—C17 | 0.5 (5) |
C1—P1—C7—C8 | 24.4 (3) | N3—C15—C16—C17 | 178.1 (3) |
C12—C7—C8—C9 | 0.3 (5) | C15—C16—C17—C18 | −0.4 (5) |
P1—C7—C8—C9 | −174.6 (3) | C16—C17—C18—C13 | −0.7 (6) |
C7—C8—C9—C10 | −1.2 (5) | C14—C13—C18—C17 | 1.5 (5) |
C7—C8—C9—N2 | 178.4 (3) | P1—C13—C18—C17 | −178.1 (3) |
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