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In the title compound, C11H11N2O7P, compression of the P—O—C angles is observed, suggesting that some strain is probably present. The configuration around phosphorus is distorted tetra­hedral. In the crystal structure, N—H...O and C—H...O hydrogen-bond contacts and van der Waals forces stabilize the packing of the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023974/at6025sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023974/at6025Isup2.hkl
Contains datablock I

CCDC reference: 282229

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.115
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(2-Nitrophenyl)-1-oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane- 4-carboxamide top
Crystal data top
C11H11N2O7PF(000) = 648
Mr = 314.19Dx = 1.653 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2576 reflections
a = 8.2381 (14) Åθ = 2.3–26.4°
b = 12.269 (2) ŵ = 0.26 mm1
c = 12.937 (2) ÅT = 293 K
β = 105.075 (3)°Prism, yellow
V = 1262.6 (4) Å30.34 × 0.28 × 0.24 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2597 independent reflections
Radiation source: fine-focus sealed tube1865 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 710
Tmin = 0.912, Tmax = 0.945k = 1513
7022 measured reflectionsl = 1614
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)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0526P)2 + 0.5183P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2597 reflectionsΔρmax = 0.28 e Å3
195 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.043 (3)
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
P10.12937 (8)1.03092 (5)0.81475 (5)0.0426 (2)
O10.1010 (2)1.13965 (13)0.77038 (15)0.0613 (5)
O20.0235 (2)0.98060 (14)0.84970 (16)0.0592 (5)
O30.1696 (3)0.94416 (13)0.73634 (13)0.0624 (5)
O40.2778 (2)1.02131 (12)0.91803 (14)0.0527 (5)
O50.1851 (3)0.71113 (15)1.03627 (16)0.0855 (7)
O60.3980 (3)0.58254 (16)0.74031 (14)0.0633 (5)
O70.4067 (2)0.41380 (17)0.69884 (15)0.0710 (6)
N10.2606 (2)0.63850 (15)0.89486 (15)0.0392 (4)
N20.3842 (2)0.48521 (18)0.75939 (16)0.0483 (5)
C10.0045 (3)0.8699 (2)0.8929 (2)0.0527 (6)
H1A0.07850.82100.84980.063*
H1B0.00810.86880.96540.063*
C20.3099 (3)0.91067 (17)0.95989 (19)0.0485 (6)
H2A0.30310.90891.03360.058*
H2B0.42240.88860.95850.058*
C30.1962 (3)0.83318 (17)0.77724 (17)0.0479 (6)
H3A0.30680.80800.77480.057*
H3B0.11290.78500.73330.057*
C40.1816 (3)0.83142 (16)0.89286 (16)0.0352 (5)
C50.2087 (3)0.71979 (18)0.94850 (17)0.0411 (5)
C60.2811 (3)0.52788 (17)0.92200 (16)0.0365 (5)
C70.2408 (3)0.48648 (18)1.01246 (18)0.0453 (6)
H70.20230.53361.05720.054*
C80.2568 (3)0.37693 (19)1.0370 (2)0.0523 (6)
H80.23060.35161.09850.063*
C90.3113 (3)0.3044 (2)0.9716 (2)0.0572 (7)
H90.32030.23050.98810.069*
C100.3519 (3)0.3424 (2)0.8822 (2)0.0531 (6)
H100.38900.29400.83790.064*
C110.3383 (3)0.45231 (18)0.85702 (17)0.0410 (5)
H10.288 (3)0.654 (2)0.840 (2)0.050 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0488 (4)0.0333 (3)0.0421 (3)0.0002 (2)0.0053 (3)0.0009 (2)
O10.0764 (13)0.0372 (9)0.0632 (11)0.0039 (8)0.0053 (9)0.0052 (8)
O20.0425 (9)0.0481 (10)0.0866 (13)0.0067 (7)0.0158 (9)0.0085 (9)
O30.1146 (15)0.0368 (9)0.0410 (9)0.0030 (9)0.0298 (10)0.0050 (7)
O40.0541 (10)0.0338 (9)0.0581 (10)0.0061 (7)0.0069 (8)0.0004 (7)
O50.174 (2)0.0438 (11)0.0627 (12)0.0184 (12)0.0733 (14)0.0100 (9)
O60.0870 (14)0.0595 (12)0.0530 (11)0.0042 (10)0.0350 (10)0.0003 (9)
O70.0778 (13)0.0747 (14)0.0703 (13)0.0112 (10)0.0372 (11)0.0223 (10)
N10.0528 (12)0.0359 (10)0.0322 (10)0.0020 (8)0.0172 (9)0.0014 (8)
N20.0407 (11)0.0589 (13)0.0460 (11)0.0065 (9)0.0127 (9)0.0096 (10)
C10.0476 (14)0.0468 (14)0.0693 (17)0.0011 (11)0.0253 (12)0.0064 (12)
C20.0541 (14)0.0361 (12)0.0466 (13)0.0024 (10)0.0023 (11)0.0006 (10)
C30.0785 (17)0.0305 (12)0.0397 (12)0.0011 (11)0.0245 (12)0.0005 (9)
C40.0426 (12)0.0326 (11)0.0326 (10)0.0017 (9)0.0136 (9)0.0021 (8)
C50.0564 (14)0.0357 (12)0.0355 (11)0.0016 (10)0.0194 (10)0.0000 (9)
C60.0367 (11)0.0363 (12)0.0333 (11)0.0003 (9)0.0036 (9)0.0018 (9)
C70.0549 (14)0.0382 (13)0.0436 (13)0.0044 (10)0.0140 (11)0.0003 (10)
C80.0635 (16)0.0418 (14)0.0497 (14)0.0070 (11)0.0111 (12)0.0055 (11)
C90.0629 (16)0.0361 (13)0.0676 (17)0.0014 (11)0.0082 (13)0.0035 (12)
C100.0507 (14)0.0449 (14)0.0601 (16)0.0048 (11)0.0078 (12)0.0119 (12)
C110.0375 (12)0.0423 (13)0.0402 (12)0.0018 (9)0.0044 (9)0.0047 (9)
Geometric parameters (Å, º) top
P1—O11.4472 (18)C2—C41.529 (3)
P1—O41.5637 (17)C2—H2A0.9700
P1—O31.5643 (18)C2—H2B0.9700
P1—O21.5710 (19)C3—C41.532 (3)
O2—C11.464 (3)C3—H3A0.9700
O3—C31.457 (3)C3—H3B0.9700
O4—C21.460 (3)C4—C51.536 (3)
O5—C51.206 (3)C6—C71.393 (3)
O6—N21.231 (3)C6—C111.412 (3)
O7—N21.221 (2)C7—C81.379 (3)
N1—C51.347 (3)C7—H70.9300
N1—C61.401 (3)C8—C91.382 (4)
N1—H10.82 (3)C8—H80.9300
N2—C111.466 (3)C9—C101.366 (4)
C1—C41.534 (3)C9—H90.9300
C1—H1A0.9700C10—C111.385 (3)
C1—H1B0.9700C10—H100.9300
O1—P1—O4114.72 (10)O3—C3—H3B109.9
O1—P1—O3114.18 (10)C4—C3—H3B109.9
O4—P1—O3104.62 (10)H3A—C3—H3B108.3
O1—P1—O2114.69 (11)C2—C4—C3109.06 (19)
O4—P1—O2103.41 (10)C2—C4—C1108.74 (19)
O3—P1—O2103.90 (11)C3—C4—C1108.22 (19)
C1—O2—P1114.59 (14)C2—C4—C5107.84 (17)
C3—O3—P1115.97 (13)C3—C4—C5115.55 (17)
C2—O4—P1114.39 (13)C1—C4—C5107.26 (17)
C5—N1—C6128.45 (19)O5—C5—N1124.8 (2)
C5—N1—H1118.0 (18)O5—C5—C4118.71 (19)
C6—N1—H1113.5 (18)N1—C5—C4116.47 (18)
O7—N2—O6122.0 (2)C7—C6—N1121.63 (19)
O7—N2—C11118.1 (2)C7—C6—C11116.8 (2)
O6—N2—C11119.86 (18)N1—C6—C11121.6 (2)
O2—C1—C4109.92 (18)C8—C7—C6121.3 (2)
O2—C1—H1A109.7C8—C7—H7119.4
C4—C1—H1A109.7C6—C7—H7119.4
O2—C1—H1B109.7C7—C8—C9120.9 (2)
C4—C1—H1B109.7C7—C8—H8119.6
H1A—C1—H1B108.2C9—C8—H8119.6
O4—C2—C4110.44 (17)C10—C9—C8119.3 (2)
O4—C2—H2A109.6C10—C9—H9120.4
C4—C2—H2A109.6C8—C9—H9120.4
O4—C2—H2B109.6C9—C10—C11120.6 (2)
C4—C2—H2B109.6C9—C10—H10119.7
H2A—C2—H2B108.1C11—C10—H10119.7
O3—C3—C4108.98 (17)C10—C11—C6121.2 (2)
O3—C3—H3A109.9C10—C11—N2116.6 (2)
C4—C3—H3A109.9C6—C11—N2122.2 (2)
O1—P1—O2—C1179.05 (17)C2—C4—C5—O563.8 (3)
O4—P1—O2—C155.31 (19)C3—C4—C5—O5173.9 (2)
O3—P1—O2—C153.73 (19)C1—C4—C5—O553.1 (3)
O1—P1—O3—C3179.01 (17)C2—C4—C5—N1115.1 (2)
O4—P1—O3—C354.8 (2)C3—C4—C5—N17.2 (3)
O2—P1—O3—C353.4 (2)C1—C4—C5—N1128.0 (2)
O1—P1—O4—C2177.69 (17)C5—N1—C6—C72.6 (3)
O3—P1—O4—C251.81 (19)C5—N1—C6—C11179.6 (2)
O2—P1—O4—C256.69 (18)N1—C6—C7—C8178.2 (2)
P1—O2—C1—C40.2 (3)C11—C6—C7—C80.2 (3)
P1—O4—C2—C42.5 (3)C6—C7—C8—C90.9 (4)
P1—O3—C3—C41.5 (3)C7—C8—C9—C100.9 (4)
O4—C2—C4—C360.5 (2)C8—C9—C10—C110.2 (4)
O4—C2—C4—C157.3 (2)C9—C10—C11—C60.5 (4)
O4—C2—C4—C5173.34 (18)C9—C10—C11—N2179.8 (2)
O3—C3—C4—C257.7 (2)C7—C6—C11—C100.5 (3)
O3—C3—C4—C160.5 (2)N1—C6—C11—C10177.5 (2)
O3—C3—C4—C5179.30 (19)C7—C6—C11—N2179.77 (19)
O2—C1—C4—C258.5 (2)N1—C6—C11—N21.8 (3)
O2—C1—C4—C359.9 (2)O7—N2—C11—C1010.7 (3)
O2—C1—C4—C5174.83 (18)O6—N2—C11—C10169.7 (2)
C6—N1—C5—O57.2 (4)O7—N2—C11—C6168.6 (2)
C6—N1—C5—C4174.01 (19)O6—N2—C11—C611.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O60.82 (3)1.97 (3)2.632 (3)138 (2)
N1—H1···N20.82 (3)2.54 (2)2.928 (3)111 (2)
C2—H2A···O6i0.972.593.511 (3)159
C3—H3B···O1ii0.972.503.351 (3)147
C7—H7···O50.932.192.824 (3)124
C7—H7···O3i0.932.423.216 (3)144
C10—H10···O70.932.362.675 (3)100
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y1/2, z+3/2.
 

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