In the title compound, C
11H
11N
2O
7P, 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
CCDC reference: 282229
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.115
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
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
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
C11H11N2O7P | F(000) = 648 |
Mr = 314.19 | Dx = 1.653 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2576 reflections |
a = 8.2381 (14) Å | θ = 2.3–26.4° |
b = 12.269 (2) Å | µ = 0.26 mm−1 |
c = 12.937 (2) Å | T = 293 K |
β = 105.075 (3)° | Prism, yellow |
V = 1262.6 (4) Å3 | 0.34 × 0.28 × 0.24 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2597 independent reflections |
Radiation source: fine-focus sealed tube | 1865 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→10 |
Tmin = 0.912, Tmax = 0.945 | k = −15→13 |
7022 measured reflections | l = −16→14 |
Refinement top
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) = 0.115 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.5183P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2597 reflections | Δρmax = 0.28 e Å−3 |
195 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
P1 | 0.12937 (8) | 1.03092 (5) | 0.81475 (5) | 0.0426 (2) | |
O1 | 0.1010 (2) | 1.13965 (13) | 0.77038 (15) | 0.0613 (5) | |
O2 | −0.0235 (2) | 0.98060 (14) | 0.84970 (16) | 0.0592 (5) | |
O3 | 0.1696 (3) | 0.94416 (13) | 0.73634 (13) | 0.0624 (5) | |
O4 | 0.2778 (2) | 1.02131 (12) | 0.91803 (14) | 0.0527 (5) | |
O5 | 0.1851 (3) | 0.71113 (15) | 1.03627 (16) | 0.0855 (7) | |
O6 | 0.3980 (3) | 0.58254 (16) | 0.74031 (14) | 0.0633 (5) | |
O7 | 0.4067 (2) | 0.41380 (17) | 0.69884 (15) | 0.0710 (6) | |
N1 | 0.2606 (2) | 0.63850 (15) | 0.89486 (15) | 0.0392 (4) | |
N2 | 0.3842 (2) | 0.48521 (18) | 0.75939 (16) | 0.0483 (5) | |
C1 | 0.0045 (3) | 0.8699 (2) | 0.8929 (2) | 0.0527 (6) | |
H1A | −0.0785 | 0.8210 | 0.8498 | 0.063* | |
H1B | −0.0081 | 0.8688 | 0.9654 | 0.063* | |
C2 | 0.3099 (3) | 0.91067 (17) | 0.95989 (19) | 0.0485 (6) | |
H2A | 0.3031 | 0.9089 | 1.0336 | 0.058* | |
H2B | 0.4224 | 0.8886 | 0.9585 | 0.058* | |
C3 | 0.1962 (3) | 0.83318 (17) | 0.77724 (17) | 0.0479 (6) | |
H3A | 0.3068 | 0.8080 | 0.7748 | 0.057* | |
H3B | 0.1129 | 0.7850 | 0.7333 | 0.057* | |
C4 | 0.1816 (3) | 0.83142 (16) | 0.89286 (16) | 0.0352 (5) | |
C5 | 0.2087 (3) | 0.71979 (18) | 0.94850 (17) | 0.0411 (5) | |
C6 | 0.2811 (3) | 0.52788 (17) | 0.92200 (16) | 0.0365 (5) | |
C7 | 0.2408 (3) | 0.48648 (18) | 1.01246 (18) | 0.0453 (6) | |
H7 | 0.2023 | 0.5336 | 1.0572 | 0.054* | |
C8 | 0.2568 (3) | 0.37693 (19) | 1.0370 (2) | 0.0523 (6) | |
H8 | 0.2306 | 0.3516 | 1.0985 | 0.063* | |
C9 | 0.3113 (3) | 0.3044 (2) | 0.9716 (2) | 0.0572 (7) | |
H9 | 0.3203 | 0.2305 | 0.9881 | 0.069* | |
C10 | 0.3519 (3) | 0.3424 (2) | 0.8822 (2) | 0.0531 (6) | |
H10 | 0.3890 | 0.2940 | 0.8379 | 0.064* | |
C11 | 0.3383 (3) | 0.45231 (18) | 0.85702 (17) | 0.0410 (5) | |
H1 | 0.288 (3) | 0.654 (2) | 0.840 (2) | 0.050 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0488 (4) | 0.0333 (3) | 0.0421 (3) | 0.0002 (2) | 0.0053 (3) | −0.0009 (2) |
O1 | 0.0764 (13) | 0.0372 (9) | 0.0632 (11) | 0.0039 (8) | 0.0053 (9) | 0.0052 (8) |
O2 | 0.0425 (9) | 0.0481 (10) | 0.0866 (13) | 0.0067 (7) | 0.0158 (9) | 0.0085 (9) |
O3 | 0.1146 (15) | 0.0368 (9) | 0.0410 (9) | 0.0030 (9) | 0.0298 (10) | 0.0050 (7) |
O4 | 0.0541 (10) | 0.0338 (9) | 0.0581 (10) | −0.0061 (7) | −0.0069 (8) | 0.0004 (7) |
O5 | 0.174 (2) | 0.0438 (11) | 0.0627 (12) | 0.0184 (12) | 0.0733 (14) | 0.0100 (9) |
O6 | 0.0870 (14) | 0.0595 (12) | 0.0530 (11) | 0.0042 (10) | 0.0350 (10) | 0.0003 (9) |
O7 | 0.0778 (13) | 0.0747 (14) | 0.0703 (13) | 0.0112 (10) | 0.0372 (11) | −0.0223 (10) |
N1 | 0.0528 (12) | 0.0359 (10) | 0.0322 (10) | 0.0020 (8) | 0.0172 (9) | 0.0014 (8) |
N2 | 0.0407 (11) | 0.0589 (13) | 0.0460 (11) | 0.0065 (9) | 0.0127 (9) | −0.0096 (10) |
C1 | 0.0476 (14) | 0.0468 (14) | 0.0693 (17) | 0.0011 (11) | 0.0253 (12) | 0.0064 (12) |
C2 | 0.0541 (14) | 0.0361 (12) | 0.0466 (13) | −0.0024 (10) | −0.0023 (11) | 0.0006 (10) |
C3 | 0.0785 (17) | 0.0305 (12) | 0.0397 (12) | −0.0011 (11) | 0.0245 (12) | 0.0005 (9) |
C4 | 0.0426 (12) | 0.0326 (11) | 0.0326 (10) | −0.0017 (9) | 0.0136 (9) | −0.0021 (8) |
C5 | 0.0564 (14) | 0.0357 (12) | 0.0355 (11) | −0.0016 (10) | 0.0194 (10) | 0.0000 (9) |
C6 | 0.0367 (11) | 0.0363 (12) | 0.0333 (11) | −0.0003 (9) | 0.0036 (9) | −0.0018 (9) |
C7 | 0.0549 (14) | 0.0382 (13) | 0.0436 (13) | −0.0044 (10) | 0.0140 (11) | 0.0003 (10) |
C8 | 0.0635 (16) | 0.0418 (14) | 0.0497 (14) | −0.0070 (11) | 0.0111 (12) | 0.0055 (11) |
C9 | 0.0629 (16) | 0.0361 (13) | 0.0676 (17) | 0.0014 (11) | 0.0082 (13) | 0.0035 (12) |
C10 | 0.0507 (14) | 0.0449 (14) | 0.0601 (16) | 0.0048 (11) | 0.0078 (12) | −0.0119 (12) |
C11 | 0.0375 (12) | 0.0423 (13) | 0.0402 (12) | 0.0018 (9) | 0.0044 (9) | −0.0047 (9) |
Geometric parameters (Å, º) top
P1—O1 | 1.4472 (18) | C2—C4 | 1.529 (3) |
P1—O4 | 1.5637 (17) | C2—H2A | 0.9700 |
P1—O3 | 1.5643 (18) | C2—H2B | 0.9700 |
P1—O2 | 1.5710 (19) | C3—C4 | 1.532 (3) |
O2—C1 | 1.464 (3) | C3—H3A | 0.9700 |
O3—C3 | 1.457 (3) | C3—H3B | 0.9700 |
O4—C2 | 1.460 (3) | C4—C5 | 1.536 (3) |
O5—C5 | 1.206 (3) | C6—C7 | 1.393 (3) |
O6—N2 | 1.231 (3) | C6—C11 | 1.412 (3) |
O7—N2 | 1.221 (2) | C7—C8 | 1.379 (3) |
N1—C5 | 1.347 (3) | C7—H7 | 0.9300 |
N1—C6 | 1.401 (3) | C8—C9 | 1.382 (4) |
N1—H1 | 0.82 (3) | C8—H8 | 0.9300 |
N2—C11 | 1.466 (3) | C9—C10 | 1.366 (4) |
C1—C4 | 1.534 (3) | C9—H9 | 0.9300 |
C1—H1A | 0.9700 | C10—C11 | 1.385 (3) |
C1—H1B | 0.9700 | C10—H10 | 0.9300 |
| | | |
O1—P1—O4 | 114.72 (10) | O3—C3—H3B | 109.9 |
O1—P1—O3 | 114.18 (10) | C4—C3—H3B | 109.9 |
O4—P1—O3 | 104.62 (10) | H3A—C3—H3B | 108.3 |
O1—P1—O2 | 114.69 (11) | C2—C4—C3 | 109.06 (19) |
O4—P1—O2 | 103.41 (10) | C2—C4—C1 | 108.74 (19) |
O3—P1—O2 | 103.90 (11) | C3—C4—C1 | 108.22 (19) |
C1—O2—P1 | 114.59 (14) | C2—C4—C5 | 107.84 (17) |
C3—O3—P1 | 115.97 (13) | C3—C4—C5 | 115.55 (17) |
C2—O4—P1 | 114.39 (13) | C1—C4—C5 | 107.26 (17) |
C5—N1—C6 | 128.45 (19) | O5—C5—N1 | 124.8 (2) |
C5—N1—H1 | 118.0 (18) | O5—C5—C4 | 118.71 (19) |
C6—N1—H1 | 113.5 (18) | N1—C5—C4 | 116.47 (18) |
O7—N2—O6 | 122.0 (2) | C7—C6—N1 | 121.63 (19) |
O7—N2—C11 | 118.1 (2) | C7—C6—C11 | 116.8 (2) |
O6—N2—C11 | 119.86 (18) | N1—C6—C11 | 121.6 (2) |
O2—C1—C4 | 109.92 (18) | C8—C7—C6 | 121.3 (2) |
O2—C1—H1A | 109.7 | C8—C7—H7 | 119.4 |
C4—C1—H1A | 109.7 | C6—C7—H7 | 119.4 |
O2—C1—H1B | 109.7 | C7—C8—C9 | 120.9 (2) |
C4—C1—H1B | 109.7 | C7—C8—H8 | 119.6 |
H1A—C1—H1B | 108.2 | C9—C8—H8 | 119.6 |
O4—C2—C4 | 110.44 (17) | C10—C9—C8 | 119.3 (2) |
O4—C2—H2A | 109.6 | C10—C9—H9 | 120.4 |
C4—C2—H2A | 109.6 | C8—C9—H9 | 120.4 |
O4—C2—H2B | 109.6 | C9—C10—C11 | 120.6 (2) |
C4—C2—H2B | 109.6 | C9—C10—H10 | 119.7 |
H2A—C2—H2B | 108.1 | C11—C10—H10 | 119.7 |
O3—C3—C4 | 108.98 (17) | C10—C11—C6 | 121.2 (2) |
O3—C3—H3A | 109.9 | C10—C11—N2 | 116.6 (2) |
C4—C3—H3A | 109.9 | C6—C11—N2 | 122.2 (2) |
| | | |
O1—P1—O2—C1 | 179.05 (17) | C2—C4—C5—O5 | 63.8 (3) |
O4—P1—O2—C1 | −55.31 (19) | C3—C4—C5—O5 | −173.9 (2) |
O3—P1—O2—C1 | 53.73 (19) | C1—C4—C5—O5 | −53.1 (3) |
O1—P1—O3—C3 | −179.01 (17) | C2—C4—C5—N1 | −115.1 (2) |
O4—P1—O3—C3 | 54.8 (2) | C3—C4—C5—N1 | 7.2 (3) |
O2—P1—O3—C3 | −53.4 (2) | C1—C4—C5—N1 | 128.0 (2) |
O1—P1—O4—C2 | −177.69 (17) | C5—N1—C6—C7 | 2.6 (3) |
O3—P1—O4—C2 | −51.81 (19) | C5—N1—C6—C11 | −179.6 (2) |
O2—P1—O4—C2 | 56.69 (18) | N1—C6—C7—C8 | 178.2 (2) |
P1—O2—C1—C4 | 0.2 (3) | C11—C6—C7—C8 | 0.2 (3) |
P1—O4—C2—C4 | −2.5 (3) | C6—C7—C8—C9 | −0.9 (4) |
P1—O3—C3—C4 | −1.5 (3) | C7—C8—C9—C10 | 0.9 (4) |
O4—C2—C4—C3 | 60.5 (2) | C8—C9—C10—C11 | −0.2 (4) |
O4—C2—C4—C1 | −57.3 (2) | C9—C10—C11—C6 | −0.5 (4) |
O4—C2—C4—C5 | −173.34 (18) | C9—C10—C11—N2 | −179.8 (2) |
O3—C3—C4—C2 | −57.7 (2) | C7—C6—C11—C10 | 0.5 (3) |
O3—C3—C4—C1 | 60.5 (2) | N1—C6—C11—C10 | −177.5 (2) |
O3—C3—C4—C5 | −179.30 (19) | C7—C6—C11—N2 | 179.77 (19) |
O2—C1—C4—C2 | 58.5 (2) | N1—C6—C11—N2 | 1.8 (3) |
O2—C1—C4—C3 | −59.9 (2) | O7—N2—C11—C10 | 10.7 (3) |
O2—C1—C4—C5 | 174.83 (18) | O6—N2—C11—C10 | −169.7 (2) |
C6—N1—C5—O5 | 7.2 (4) | O7—N2—C11—C6 | −168.6 (2) |
C6—N1—C5—C4 | −174.01 (19) | O6—N2—C11—C6 | 11.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6 | 0.82 (3) | 1.97 (3) | 2.632 (3) | 138 (2) |
N1—H1···N2 | 0.82 (3) | 2.54 (2) | 2.928 (3) | 111 (2) |
C2—H2A···O6i | 0.97 | 2.59 | 3.511 (3) | 159 |
C3—H3B···O1ii | 0.97 | 2.50 | 3.351 (3) | 147 |
C7—H7···O5 | 0.93 | 2.19 | 2.824 (3) | 124 |
C7—H7···O3i | 0.93 | 2.42 | 3.216 (3) | 144 |
C10—H10···O7 | 0.93 | 2.36 | 2.675 (3) | 100 |
Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, y−1/2, −z+3/2. |