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The title compound, C18H15N3O7P, has a P=O bond length of 1.486 (2) Å. The P-C bond lengths range from 1.806 (4) to 1.812 (3) Å, and the C-N bond distances are in the range 1.471 (4)-1.479 (5) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020732/su6134sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020732/su6134Isup2.hkl
Contains datablock I

CCDC reference: 251759

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](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

Computing details top

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.

tris(3-nitrophenyl)phosphine oxide top
Crystal data top
C18H12N3O7PF(000) = 848
Mr = 413.28Dx = 1.555 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2409 reflections
a = 19.1402 (9) Åθ = 2.5–28.3°
b = 5.4608 (2) ŵ = 0.21 mm1
c = 16.8888 (7) ÅT = 105 K
V = 1765.23 (13) Å3Needle, colorless
Z = 40.45 × 0.05 × 0.05 mm
Data collection top
KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
2233 independent reflections
Radiation source: fine-focus sealed tube1731 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scans with κ offsetsθmax = 28.3°, θmin = 3.2°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
h = 2525
Tmin = 0.896, Tmax = 0.990k = 77
12164 measured reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-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 reflectionsΔρmax = 0.29 e Å3
263 parametersΔρmin = 0.41 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0052 (11)
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
xyzUiso*/Ueq
P10.79288 (4)0.73595 (15)0.61513 (7)0.0136 (2)
O10.79709 (12)1.0072 (4)0.60987 (19)0.0189 (5)
O20.55803 (14)1.0206 (5)0.74225 (17)0.0274 (7)
O30.47919 (12)0.7426 (5)0.72288 (18)0.0269 (6)
O40.74673 (15)0.0293 (5)0.82389 (18)0.0261 (6)
O50.81876 (15)0.0729 (5)0.92162 (17)0.0285 (7)
O60.97054 (14)0.0028 (5)0.56494 (18)0.0265 (6)
O70.98516 (16)0.0385 (5)0.4384 (2)0.0343 (7)
N10.53813 (15)0.8245 (5)0.7136 (2)0.0205 (7)
N20.79523 (17)0.1349 (5)0.8572 (2)0.0206 (7)
N30.95912 (15)0.0642 (5)0.4957 (2)0.0198 (7)
C10.70323 (16)0.6291 (6)0.6153 (3)0.0143 (6)
C20.65604 (17)0.7648 (7)0.6604 (2)0.0155 (7)
H20.67060.90840.68760.019*
C30.58770 (18)0.6854 (6)0.6645 (2)0.0153 (8)
C40.56390 (17)0.4785 (6)0.6246 (3)0.0189 (8)
H40.51650.42820.62850.023*
C50.61127 (18)0.3479 (6)0.5791 (2)0.0180 (8)
H50.59610.20730.55080.022*
C60.68047 (18)0.4200 (6)0.5743 (2)0.0156 (7)
H60.71260.32810.54340.019*
C70.82896 (18)0.6206 (6)0.7069 (2)0.0143 (8)
C80.80087 (18)0.4157 (6)0.7441 (2)0.0146 (7)
H80.76470.32380.71970.017*
C90.82680 (18)0.3490 (6)0.8172 (2)0.0164 (8)
C100.88027 (19)0.4751 (7)0.8542 (2)0.0201 (8)
H100.89780.42260.90400.024*
C110.9077 (2)0.6798 (7)0.8169 (3)0.0245 (9)
H110.94400.77090.84160.029*
C120.88212 (17)0.7513 (6)0.7436 (2)0.0174 (8)
H120.90120.89150.71820.021*
C130.83592 (18)0.5791 (6)0.5346 (2)0.0152 (8)
C140.88292 (17)0.3876 (6)0.5477 (2)0.0145 (8)
H140.89450.33720.59990.017*
C150.91210 (17)0.2735 (6)0.4825 (2)0.0155 (7)
C160.89710 (19)0.3411 (7)0.4054 (2)0.0217 (9)
H160.91780.25770.36200.026*
C170.8509 (2)0.5346 (7)0.3930 (3)0.0232 (9)
H170.83990.58520.34060.028*
C180.82085 (19)0.6532 (7)0.4573 (2)0.0192 (8)
H180.78980.78600.44860.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0124 (3)0.0137 (4)0.0148 (4)0.0005 (3)0.0008 (4)0.0001 (4)
O10.0191 (11)0.0133 (10)0.0243 (14)0.0028 (10)0.0004 (12)0.0002 (14)
O20.0262 (15)0.0293 (15)0.0267 (17)0.0008 (12)0.0032 (13)0.0121 (14)
O30.0160 (13)0.0282 (14)0.0366 (18)0.0004 (11)0.0069 (13)0.0003 (14)
O40.0289 (15)0.0279 (13)0.0215 (15)0.0118 (13)0.0005 (13)0.0035 (14)
O50.0409 (17)0.0290 (15)0.0156 (16)0.0025 (12)0.0029 (13)0.0052 (13)
O60.0308 (15)0.0269 (14)0.0217 (15)0.0098 (12)0.0027 (14)0.0009 (14)
O70.0391 (17)0.0316 (16)0.0323 (18)0.0147 (13)0.0143 (15)0.0056 (14)
N10.0175 (16)0.0234 (17)0.0205 (18)0.0017 (13)0.0028 (15)0.0018 (14)
N20.0261 (17)0.0216 (16)0.0142 (18)0.0006 (14)0.0064 (16)0.0003 (14)
N30.0162 (15)0.0181 (15)0.025 (2)0.0005 (12)0.0027 (15)0.0006 (15)
C10.0110 (14)0.0167 (14)0.0153 (17)0.0016 (13)0.0003 (17)0.0044 (18)
C20.0169 (16)0.0172 (16)0.0124 (19)0.0011 (15)0.0030 (15)0.0009 (16)
C30.0163 (17)0.0164 (18)0.0133 (19)0.0042 (13)0.0009 (16)0.0009 (15)
C40.0118 (16)0.0212 (17)0.024 (2)0.0012 (13)0.0009 (17)0.0062 (18)
C50.0191 (18)0.0155 (16)0.020 (2)0.0017 (14)0.0050 (17)0.0006 (16)
C60.0198 (17)0.0119 (16)0.0151 (19)0.0034 (14)0.0038 (17)0.0005 (15)
C70.0122 (16)0.0177 (18)0.013 (2)0.0037 (13)0.0002 (15)0.0031 (16)
C80.0138 (16)0.0164 (17)0.0135 (19)0.0016 (14)0.0022 (16)0.0040 (15)
C90.0168 (18)0.0181 (17)0.014 (2)0.0019 (14)0.0041 (16)0.0006 (16)
C100.0194 (18)0.028 (2)0.0131 (19)0.0008 (16)0.0026 (17)0.0016 (17)
C110.024 (2)0.027 (2)0.023 (2)0.0054 (15)0.0059 (19)0.0044 (17)
C120.0149 (16)0.0165 (17)0.021 (2)0.0033 (15)0.0040 (16)0.0025 (17)
C130.0121 (17)0.0174 (18)0.016 (2)0.0043 (14)0.0011 (16)0.0016 (16)
C140.0130 (16)0.0140 (17)0.017 (2)0.0006 (14)0.0012 (15)0.0041 (14)
C150.0129 (15)0.0157 (16)0.018 (2)0.0000 (14)0.0010 (15)0.0014 (16)
C160.020 (2)0.0267 (19)0.018 (2)0.0015 (15)0.0049 (17)0.0044 (17)
C170.023 (2)0.031 (2)0.016 (2)0.0013 (17)0.0004 (17)0.0050 (18)
C180.0188 (18)0.0214 (19)0.017 (2)0.0036 (16)0.0000 (16)0.0033 (17)
Geometric parameters (Å, º) top
P1—O11.486 (2)C6—H60.9500
P1—C11.812 (3)C7—C121.389 (5)
P1—C71.810 (4)C7—C81.391 (5)
P1—C131.806 (4)C8—C91.380 (5)
O2—N11.235 (4)C8—H80.9500
O3—N11.224 (4)C9—C101.382 (5)
O4—N21.229 (4)C10—C111.386 (6)
O5—N21.225 (4)C10—H100.9500
O6—N31.236 (4)C11—C121.388 (6)
O7—N31.225 (4)C11—H110.9500
N1—C31.471 (5)C12—H120.9500
N2—C91.479 (5)C13—C141.397 (5)
N3—C151.471 (4)C13—C181.398 (5)
C1—C21.395 (5)C14—C151.383 (5)
C1—C61.404 (5)C14—H140.9500
C2—C31.380 (5)C15—C161.384 (6)
C2—H20.9500C16—C171.394 (5)
C3—C41.392 (5)C16—H160.9500
C4—C51.387 (5)C17—C181.388 (6)
C4—H40.9500C17—H170.9500
C5—C61.384 (5)C18—H180.9500
C5—H50.9500
O1—P1—C13113.76 (18)C8—C7—P1121.3 (3)
O1—P1—C7112.17 (17)C9—C8—C7118.5 (3)
C13—P1—C7107.80 (16)C9—C8—H8120.7
O1—P1—C1111.87 (14)C7—C8—H8120.7
C13—P1—C1106.27 (18)C8—C9—C10122.6 (3)
C7—P1—C1104.36 (18)C8—C9—N2118.1 (3)
O3—N1—O2123.5 (3)C10—C9—N2119.4 (3)
O3—N1—C3118.5 (3)C9—C10—C11118.6 (4)
O2—N1—C3118.0 (3)C9—C10—H10120.7
O5—N2—O4123.7 (3)C11—C10—H10120.7
O5—N2—C9118.3 (3)C10—C11—C12119.8 (4)
O4—N2—C9118.1 (3)C10—C11—H11120.1
O7—N3—O6123.5 (3)C12—C11—H11120.1
O7—N3—C15119.0 (3)C11—C12—C7120.8 (4)
O6—N3—C15117.5 (3)C11—C12—H12119.6
C2—C1—C6120.0 (3)C7—C12—H12119.6
C2—C1—P1116.3 (3)C14—C13—C18119.8 (3)
C6—C1—P1123.7 (3)C14—C13—P1122.0 (3)
C3—C2—C1118.3 (3)C18—C13—P1118.2 (3)
C3—C2—H2120.8C15—C14—C13118.1 (3)
C1—C2—H2120.8C15—C14—H14120.9
C2—C3—C4122.7 (3)C13—C14—H14120.9
C2—C3—N1118.5 (3)C14—C15—C16123.0 (3)
C4—C3—N1118.7 (3)C14—C15—N3118.5 (3)
C5—C4—C3118.2 (3)C16—C15—N3118.5 (3)
C5—C4—H4120.9C15—C16—C17118.4 (4)
C3—C4—H4120.9C15—C16—H16120.8
C6—C5—C4120.8 (3)C17—C16—H16120.8
C6—C5—H5119.6C18—C17—C16119.9 (4)
C4—C5—H5119.6C18—C17—H17120.1
C5—C6—C1120.0 (3)C16—C17—H17120.1
C5—C6—H6120.0C17—C18—C13120.7 (3)
C1—C6—H6120.0C17—C18—H18119.6
C12—C7—C8119.7 (4)C13—C18—H18119.6
C12—C7—P1118.9 (3)
O1—P1—C1—C241.1 (4)O5—N2—C9—C8179.0 (3)
C13—P1—C1—C2165.9 (3)O4—N2—C9—C81.1 (5)
C7—P1—C1—C280.4 (3)O5—N2—C9—C101.5 (5)
O1—P1—C1—C6140.0 (3)O4—N2—C9—C10178.4 (3)
C13—P1—C1—C615.3 (4)C8—C9—C10—C111.5 (6)
C7—P1—C1—C698.5 (4)N2—C9—C10—C11178.0 (3)
C6—C1—C2—C31.2 (6)C9—C10—C11—C121.0 (6)
P1—C1—C2—C3177.7 (3)C10—C11—C12—C70.2 (6)
C1—C2—C3—C41.1 (6)C8—C7—C12—C110.1 (5)
C1—C2—C3—N1178.5 (3)P1—C7—C12—C11175.2 (3)
O3—N1—C3—C2173.7 (3)O1—P1—C13—C14130.8 (3)
O2—N1—C3—C27.5 (5)C7—P1—C13—C145.7 (3)
O3—N1—C3—C45.8 (5)C1—P1—C13—C14105.7 (3)
O2—N1—C3—C4172.9 (3)O1—P1—C13—C1849.5 (3)
C2—C3—C4—C50.1 (6)C7—P1—C13—C18174.6 (3)
N1—C3—C4—C5179.5 (3)C1—P1—C13—C1874.0 (3)
C3—C4—C5—C60.8 (6)C18—C13—C14—C151.3 (5)
C4—C5—C6—C10.7 (6)P1—C13—C14—C15178.3 (3)
C2—C1—C6—C50.4 (6)C13—C14—C15—C160.3 (5)
P1—C1—C6—C5178.5 (3)C13—C14—C15—N3177.2 (3)
O1—P1—C7—C1229.2 (3)O7—N3—C15—C14179.9 (3)
C13—P1—C7—C1296.7 (3)O6—N3—C15—C140.6 (5)
C1—P1—C7—C12150.5 (3)O7—N3—C15—C162.2 (5)
O1—P1—C7—C8145.7 (3)O6—N3—C15—C16178.3 (3)
C13—P1—C7—C888.3 (3)C14—C15—C16—C170.5 (5)
C1—P1—C7—C824.4 (3)N3—C15—C16—C17178.1 (3)
C12—C7—C8—C90.3 (5)C15—C16—C17—C180.4 (5)
P1—C7—C8—C9174.6 (3)C16—C17—C18—C130.7 (6)
C7—C8—C9—C101.2 (5)C14—C13—C18—C171.5 (5)
C7—C8—C9—N2178.4 (3)P1—C13—C18—C17178.1 (3)
 

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