Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042340/sj6184sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042340/sj6184Isup2.hkl |
CCDC reference: 296669
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.152
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.706 PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N1 .. 5.85 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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
The title compound was prepared by the method of Grawe et al. (2002). Single crystals suitable for crystallographic analysis were obtained by slow evaporation of a tetrahydrofuran solution [m.p. 441 (2) K]. IR (KBr, ν, cm−1): 1502 (CN), 1195 (PO). 1H NMR (DMSO): δ 7.64—7.61 (m, 2H), 7.41–7.39 (m, 1H), 3.61 (s, 3H), 3.58 (s, 3H), 3.31 (s, 1H), 3.27 (s, 1H).
All H atoms were refined using a riding model, with C—H = 0.93 Å and Uiso = 1.2Ueq(C) for aromatic H atoms, C—H = 0.97 Å and Uiso = 1.2Ueq(C) for CH2 H atoms, C—H = 0.96 Å and Uiso = 1.5Ueq(C) for CH3 H atoms, and O—H = 0.82 Å and Uiso = 1.5Ueq(C) for OH H atoms.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C9H12NO6P | F(000) = 544 |
Mr = 261.17 | Dx = 1.488 Mg m−3 |
Monoclinic, P21/n | Melting point: 441(2) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8154 (15) Å | Cell parameters from 2199 reflections |
b = 12.963 (3) Å | θ = 2.4–26.0° |
c = 11.669 (2) Å | µ = 0.25 mm−1 |
β = 99.660 (3)° | T = 294 K |
V = 1165.4 (4) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.24 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 2408 independent reflections |
Radiation source: fine-focus sealed tube | 1671 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ϕ and ω scans | θmax = 26.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→8 |
Tmin = 0.915, Tmax = 0.972 | k = −16→15 |
6476 measured reflections | l = −12→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 0.71 | w = 1/[σ2(Fo2) + (0.1314P)2 + 1.0878P] where P = (Fo2 + 2Fc2)/3 |
2408 reflections | (Δ/σ)max = 0.002 |
157 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C9H12NO6P | V = 1165.4 (4) Å3 |
Mr = 261.17 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.8154 (15) Å | µ = 0.25 mm−1 |
b = 12.963 (3) Å | T = 294 K |
c = 11.669 (2) Å | 0.30 × 0.24 × 0.12 mm |
β = 99.660 (3)° |
Bruker SMART CCD area-detector diffractometer | 2408 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1671 reflections with I > 2σ(I) |
Tmin = 0.915, Tmax = 0.972 | Rint = 0.036 |
6476 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 0.71 | Δρmax = 0.19 e Å−3 |
2408 reflections | Δρmin = −0.38 e Å−3 |
157 parameters |
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 | 0.08647 (8) | 0.30331 (5) | 0.10575 (5) | 0.0373 (2) | |
O1 | 0.0878 (3) | 0.19508 (13) | 0.14275 (16) | 0.0491 (5) | |
O2 | 0.2783 (2) | 0.34014 (15) | 0.11173 (16) | 0.0521 (5) | |
O3 | −0.0138 (3) | 0.32433 (14) | −0.01981 (16) | 0.0542 (5) | |
O4 | 0.1995 (3) | 0.54684 (14) | 0.27178 (16) | 0.0551 (5) | |
H4 | 0.2660 | 0.5917 | 0.3023 | 0.083* | |
O5 | 0.3644 (3) | 0.50764 (18) | 0.69912 (17) | 0.0663 (6) | |
O6 | 0.2441 (3) | 0.3662 (2) | 0.74030 (18) | 0.0750 (7) | |
N1 | 0.2764 (3) | 0.4313 (2) | 0.67091 (19) | 0.0500 (6) | |
C1 | −0.0239 (4) | 0.3876 (2) | 0.1893 (2) | 0.0461 (6) | |
H1A | −0.0284 | 0.4559 | 0.1549 | 0.055* | |
H1B | −0.1424 | 0.3636 | 0.1849 | 0.055* | |
C2 | 0.0590 (3) | 0.39558 (18) | 0.3161 (2) | 0.0385 (6) | |
C3 | 0.0249 (3) | 0.3239 (2) | 0.3975 (2) | 0.0470 (6) | |
H3 | −0.0476 | 0.2684 | 0.3732 | 0.056* | |
C4 | 0.0963 (4) | 0.3330 (2) | 0.5145 (2) | 0.0476 (6) | |
H4A | 0.0729 | 0.2846 | 0.5686 | 0.057* | |
C5 | 0.2028 (3) | 0.4161 (2) | 0.5471 (2) | 0.0396 (6) | |
C6 | 0.2428 (3) | 0.48830 (18) | 0.4697 (2) | 0.0382 (5) | |
H6 | 0.3168 | 0.5429 | 0.4949 | 0.046* | |
C7 | 0.1703 (3) | 0.47825 (17) | 0.3528 (2) | 0.0377 (5) | |
C8 | 0.3249 (5) | 0.4333 (3) | 0.0558 (3) | 0.0708 (10) | |
H8A | 0.3273 | 0.4195 | −0.0248 | 0.106* | |
H8B | 0.4374 | 0.4561 | 0.0930 | 0.106* | |
H8C | 0.2408 | 0.4861 | 0.0620 | 0.106* | |
C9 | −0.0114 (4) | 0.2514 (2) | −0.1127 (2) | 0.0515 (7) | |
H9A | 0.1066 | 0.2354 | −0.1189 | 0.077* | |
H9B | −0.0687 | 0.2808 | −0.1845 | 0.077* | |
H9C | −0.0706 | 0.1895 | −0.0966 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0421 (4) | 0.0322 (4) | 0.0352 (4) | 0.0033 (3) | −0.0001 (3) | −0.0009 (2) |
O1 | 0.0642 (13) | 0.0326 (10) | 0.0500 (11) | 0.0039 (8) | 0.0078 (9) | 0.0009 (8) |
O2 | 0.0445 (11) | 0.0596 (12) | 0.0517 (11) | −0.0017 (9) | 0.0069 (9) | 0.0090 (9) |
O3 | 0.0706 (13) | 0.0463 (11) | 0.0381 (10) | 0.0097 (9) | −0.0128 (9) | −0.0051 (8) |
O4 | 0.0796 (15) | 0.0397 (10) | 0.0405 (10) | −0.0087 (9) | −0.0055 (9) | 0.0034 (8) |
O5 | 0.0774 (15) | 0.0716 (14) | 0.0436 (11) | −0.0038 (12) | −0.0078 (10) | −0.0119 (10) |
O6 | 0.0745 (15) | 0.1102 (19) | 0.0423 (11) | −0.0030 (14) | 0.0157 (10) | 0.0188 (12) |
N1 | 0.0474 (13) | 0.0667 (15) | 0.0368 (12) | 0.0145 (12) | 0.0099 (10) | 0.0016 (11) |
C1 | 0.0431 (14) | 0.0439 (14) | 0.0467 (15) | 0.0072 (11) | −0.0057 (11) | −0.0094 (11) |
C2 | 0.0355 (12) | 0.0376 (13) | 0.0412 (13) | 0.0072 (10) | 0.0032 (10) | −0.0089 (10) |
C3 | 0.0420 (14) | 0.0447 (14) | 0.0546 (16) | −0.0063 (11) | 0.0094 (12) | −0.0100 (12) |
C4 | 0.0497 (16) | 0.0451 (14) | 0.0512 (16) | −0.0018 (12) | 0.0175 (13) | 0.0039 (12) |
C5 | 0.0366 (13) | 0.0457 (14) | 0.0370 (13) | 0.0070 (10) | 0.0077 (10) | −0.0049 (10) |
C6 | 0.0405 (13) | 0.0328 (12) | 0.0402 (13) | 0.0026 (10) | 0.0030 (10) | −0.0055 (10) |
C7 | 0.0435 (13) | 0.0313 (12) | 0.0370 (12) | 0.0069 (10) | 0.0027 (10) | −0.0025 (10) |
C8 | 0.084 (2) | 0.074 (2) | 0.0568 (19) | −0.0265 (19) | 0.0164 (17) | 0.0059 (16) |
C9 | 0.0664 (19) | 0.0530 (17) | 0.0350 (13) | −0.0104 (14) | 0.0082 (12) | −0.0048 (11) |
P1—O1 | 1.4673 (19) | C2—C7 | 1.401 (3) |
P1—O2 | 1.563 (2) | C3—C4 | 1.390 (4) |
P1—O3 | 1.5653 (18) | C3—H3 | 0.9300 |
P1—C1 | 1.781 (3) | C4—C5 | 1.376 (4) |
O2—C8 | 1.449 (4) | C4—H4A | 0.9300 |
O3—C9 | 1.441 (3) | C5—C6 | 1.372 (4) |
O4—C7 | 1.345 (3) | C6—C7 | 1.392 (3) |
O4—H4 | 0.8200 | C6—H6 | 0.9300 |
O5—N1 | 1.219 (3) | C8—H8A | 0.9600 |
O6—N1 | 1.225 (3) | C8—H8B | 0.9600 |
N1—C5 | 1.476 (3) | C8—H8C | 0.9600 |
C1—C2 | 1.516 (3) | C9—H9A | 0.9600 |
C1—H1A | 0.9700 | C9—H9B | 0.9600 |
C1—H1B | 0.9700 | C9—H9C | 0.9600 |
C2—C3 | 1.386 (4) | ||
O1—P1—O2 | 108.62 (11) | C5—C4—C3 | 117.5 (2) |
O1—P1—O3 | 114.82 (11) | C5—C4—H4A | 121.2 |
O2—P1—O3 | 108.33 (11) | C3—C4—H4A | 121.2 |
O1—P1—C1 | 113.95 (13) | C6—C5—C4 | 123.1 (2) |
O2—P1—C1 | 109.70 (12) | C6—C5—N1 | 117.3 (2) |
O3—P1—C1 | 101.12 (12) | C4—C5—N1 | 119.6 (2) |
C8—O2—P1 | 123.1 (2) | C5—C6—C7 | 118.7 (2) |
C9—O3—P1 | 121.49 (18) | C5—C6—H6 | 120.6 |
C7—O4—H4 | 109.5 | C7—C6—H6 | 120.6 |
O5—N1—O6 | 123.4 (2) | O4—C7—C6 | 122.5 (2) |
O5—N1—C5 | 118.8 (2) | O4—C7—C2 | 117.4 (2) |
O6—N1—C5 | 117.8 (3) | C6—C7—C2 | 120.1 (2) |
C2—C1—P1 | 114.14 (17) | O2—C8—H8A | 109.5 |
C2—C1—H1A | 108.7 | O2—C8—H8B | 109.5 |
P1—C1—H1A | 108.7 | H8A—C8—H8B | 109.5 |
C2—C1—H1B | 108.7 | O2—C8—H8C | 109.5 |
P1—C1—H1B | 108.7 | H8A—C8—H8C | 109.5 |
H1A—C1—H1B | 107.6 | H8B—C8—H8C | 109.5 |
C3—C2—C7 | 118.9 (2) | O3—C9—H9A | 109.5 |
C3—C2—C1 | 121.6 (2) | O3—C9—H9B | 109.5 |
C7—C2—C1 | 119.5 (2) | H9A—C9—H9B | 109.5 |
C2—C3—C4 | 121.7 (2) | O3—C9—H9C | 109.5 |
C2—C3—H3 | 119.2 | H9A—C9—H9C | 109.5 |
C4—C3—H3 | 119.2 | H9B—C9—H9C | 109.5 |
O1—P1—O2—C8 | 164.7 (2) | C3—C4—C5—C6 | −1.0 (4) |
O3—P1—O2—C8 | 39.4 (2) | C3—C4—C5—N1 | 177.7 (2) |
C1—P1—O2—C8 | −70.2 (3) | O5—N1—C5—C6 | 2.0 (3) |
O1—P1—O3—C9 | −36.1 (3) | O6—N1—C5—C6 | −178.7 (2) |
O2—P1—O3—C9 | 85.5 (2) | O5—N1—C5—C4 | −176.8 (2) |
C1—P1—O3—C9 | −159.2 (2) | O6—N1—C5—C4 | 2.5 (4) |
O1—P1—C1—C2 | 63.8 (2) | C4—C5—C6—C7 | 1.1 (4) |
O2—P1—C1—C2 | −58.3 (2) | N1—C5—C6—C7 | −177.7 (2) |
O3—P1—C1—C2 | −172.52 (19) | C5—C6—C7—O4 | 178.4 (2) |
P1—C1—C2—C3 | −83.8 (3) | C5—C6—C7—C2 | 0.0 (3) |
P1—C1—C2—C7 | 97.4 (2) | C3—C2—C7—O4 | −179.5 (2) |
C7—C2—C3—C4 | 0.9 (4) | C1—C2—C7—O4 | −0.7 (3) |
C1—C2—C3—C4 | −177.8 (2) | C3—C2—C7—C6 | −0.9 (4) |
C2—C3—C4—C5 | 0.0 (4) | C1—C2—C7—C6 | 177.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.82 | 1.81 | 2.625 (3) | 175 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H12NO6P |
Mr | 261.17 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 7.8154 (15), 12.963 (3), 11.669 (2) |
β (°) | 99.660 (3) |
V (Å3) | 1165.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.30 × 0.24 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.915, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6476, 2408, 1671 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.631 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.152, 0.71 |
No. of reflections | 2408 |
No. of parameters | 157 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.38 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
C8—O2—P1 | 123.1 (2) | C9—O3—P1 | 121.49 (18) |
O1—P1—O2—C8 | 164.7 (2) | C1—P1—O3—C9 | −159.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O1i | 0.82 | 1.81 | 2.625 (3) | 175 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
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Phosphonate esters are important intermediates in the preparation of flame-retardant materials (Acher & Wakselman, 1982). As part of our work in this area, the title compound, (I), was prepared by the reaction of 1-bromomethyl-2-hydroxy-4-nitrobenzene and trimethyl phosphite (Grawe et al., 2002) and its structure is reported here (Fig. 1 and Table 1).
The benzene ring and its nitro substituent are essentially coplanar [interplanar angle = 3.4 (2)°], while the O1—P1—O2—C8 and C1—P1—O3—C9 torsion angles are 164.7 (2) and −159.2 (2)°, respectively, indicating that the atoms in these residues are also coplanar. In the crystal structure, O4—H4···O1 hydrogen bonds link the molecules into zigzag chains along the b axis (Fig. 2).