Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801006766/bt6036sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801006766/bt6036Isup2.hkl |
CCDC reference: 165675
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.134
- Data-to-parameter ratio = 17.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound was synthesized from the reaction of sodium p-nitrophenoxide and N,N-dimethylaminophosphoryl dichloride. Crystals were obtained by recrystallization from chloroform–ethanol (1/1).
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989); cell refinement: CAD-4 EXPRESS; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound at the 50% probability level. H atoms are drawn as spheres of arbitrary radii. |
C14H14N3O7P | Dx = 1.475 Mg m−3 |
Mr = 367.25 | Melting point = 143–144 K |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 9.139 (2) Å | Cell parameters from 25 reflections |
b = 11.083 (2) Å | θ = 12–18° |
c = 16.411 (3) Å | µ = 0.21 mm−1 |
β = 95.838 (2)° | T = 298 K |
V = 1653.5 (5) Å3 | Irregular block, colorless |
Z = 4 | 0.65 × 0.18 × 0.18 mm |
F(000) = 760 |
Enraf-Nonius CAD-4 diffractometer | 2557 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 30.0°, θmin = 2.5° |
ω–2θ scans | h = 0→12 |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | k = −15→0 |
Tmin = 0.898, Tmax = 0.953 | l = −23→22 |
5105 measured reflections | 3 standard reflections every 60 min |
4823 independent reflections | intensity decay: <1% |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0759P)2] where P = (Fo2 + 2Fc2)/3 |
4823 reflections | (Δ/σ)max < 0.001 |
282 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C14H14N3O7P | V = 1653.5 (5) Å3 |
Mr = 367.25 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 9.139 (2) Å | µ = 0.21 mm−1 |
b = 11.083 (2) Å | T = 298 K |
c = 16.411 (3) Å | 0.65 × 0.18 × 0.18 mm |
β = 95.838 (2)° |
Enraf-Nonius CAD-4 diffractometer | 2557 reflections with I > 2σ(I) |
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968) | Rint = 0.016 |
Tmin = 0.898, Tmax = 0.953 | 3 standard reflections every 60 min |
5105 measured reflections | intensity decay: <1% |
4823 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 0.92 | Δρmax = 0.21 e Å−3 |
4823 reflections | Δρmin = −0.26 e Å−3 |
282 parameters |
x | y | z | Uiso*/Ueq | ||
P1 | 0.52277 (5) | 0.46416 (4) | 0.27788 (3) | 0.04861 (15) | |
O1 | 0.65806 (15) | 0.52294 (11) | 0.33169 (8) | 0.0580 (4) | |
O2 | 0.9657 (2) | 0.36753 (18) | 0.67212 (10) | 0.0899 (5) | |
O3 | 1.0619 (2) | 0.23912 (18) | 0.59589 (11) | 0.0969 (6) | |
O4 | 0.61086 (14) | 0.36642 (12) | 0.23028 (8) | 0.0583 (4) | |
O5 | 0.3742 (2) | −0.10725 (16) | 0.05943 (12) | 0.0947 (6) | |
O6 | 0.2380 (3) | 0.02187 (19) | −0.00993 (12) | 0.1161 (8) | |
O7 | 0.40922 (15) | 0.41214 (12) | 0.32308 (9) | 0.0612 (4) | |
N1 | 0.9786 (2) | 0.32234 (17) | 0.60607 (11) | 0.0634 (4) | |
N2 | 0.3342 (2) | −0.0039 (2) | 0.04428 (12) | 0.0728 (5) | |
N3 | 0.46889 (17) | 0.56651 (15) | 0.21257 (10) | 0.0554 (4) | |
C1 | 0.73351 (19) | 0.46569 (16) | 0.39975 (11) | 0.0488 (4) | |
C2 | 0.8331 (2) | 0.37487 (19) | 0.38961 (13) | 0.0579 (5) | |
C3 | 0.9124 (2) | 0.32727 (19) | 0.45735 (13) | 0.0577 (5) | |
C4 | 0.8912 (2) | 0.37177 (16) | 0.53312 (11) | 0.0490 (4) | |
C5 | 0.7908 (2) | 0.46074 (18) | 0.54392 (13) | 0.0575 (5) | |
C6 | 0.7107 (2) | 0.50799 (19) | 0.47591 (13) | 0.0575 (5) | |
C7 | 0.53685 (19) | 0.27564 (17) | 0.18405 (11) | 0.0490 (4) | |
C8 | 0.5683 (2) | 0.15850 (19) | 0.20631 (13) | 0.0612 (5) | |
C9 | 0.5008 (2) | 0.0665 (2) | 0.16059 (14) | 0.0636 (5) | |
C10 | 0.4038 (2) | 0.09416 (18) | 0.09400 (11) | 0.0531 (5) | |
C11 | 0.3700 (3) | 0.2107 (2) | 0.07197 (13) | 0.0657 (6) | |
C12 | 0.4380 (3) | 0.3028 (2) | 0.11770 (13) | 0.0656 (6) | |
C13 | 0.3291 (3) | 0.6297 (2) | 0.21513 (17) | 0.0696 (6) | |
C14 | 0.5698 (4) | 0.6232 (3) | 0.1607 (2) | 0.0929 (9) | |
H3 | 0.979 (3) | 0.269 (2) | 0.4549 (14) | 0.072 (7)* | |
H2 | 0.849 (2) | 0.3467 (19) | 0.3405 (14) | 0.067 (6)* | |
H5 | 0.771 (2) | 0.4874 (18) | 0.5960 (14) | 0.066 (6)* | |
H6 | 0.645 (2) | 0.573 (2) | 0.4775 (14) | 0.075 (7)* | |
H8 | 0.635 (3) | 0.141 (2) | 0.2532 (15) | 0.082 (7)* | |
H9 | 0.526 (3) | −0.011 (2) | 0.1710 (14) | 0.075 (7)* | |
H11 | 0.302 (3) | 0.228 (2) | 0.0270 (17) | 0.098 (8)* | |
H12 | 0.421 (2) | 0.383 (2) | 0.1011 (14) | 0.078 (7)* | |
H13A | 0.280 (2) | 0.625 (2) | 0.1605 (16) | 0.076 (7)* | |
H13B | 0.268 (3) | 0.591 (3) | 0.2550 (19) | 0.109 (10)* | |
H13C | 0.352 (3) | 0.711 (3) | 0.2305 (18) | 0.104 (9)* | |
H14A | 0.530 (3) | 0.632 (3) | 0.104 (2) | 0.112 (10)* | |
H14B | 0.586 (4) | 0.718 (3) | 0.176 (2) | 0.134 (12)* | |
H14C | 0.669 (4) | 0.585 (3) | 0.170 (2) | 0.125 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0462 (3) | 0.0482 (3) | 0.0501 (3) | −0.0012 (2) | −0.00152 (19) | −0.0030 (2) |
O1 | 0.0579 (8) | 0.0510 (7) | 0.0613 (8) | −0.0060 (6) | −0.0128 (6) | −0.0024 (6) |
O2 | 0.1024 (13) | 0.1145 (14) | 0.0507 (9) | 0.0183 (11) | −0.0025 (9) | −0.0023 (9) |
O3 | 0.1104 (14) | 0.0940 (12) | 0.0824 (11) | 0.0446 (11) | −0.0093 (11) | 0.0054 (10) |
O4 | 0.0481 (7) | 0.0620 (8) | 0.0628 (8) | 0.0056 (6) | −0.0046 (6) | −0.0133 (7) |
O5 | 0.1088 (14) | 0.0669 (11) | 0.1068 (14) | −0.0050 (10) | 0.0034 (11) | −0.0271 (10) |
O6 | 0.1411 (18) | 0.1054 (15) | 0.0894 (13) | −0.0263 (13) | −0.0487 (14) | −0.0128 (11) |
O7 | 0.0599 (8) | 0.0631 (8) | 0.0618 (8) | −0.0059 (7) | 0.0114 (7) | 0.0018 (7) |
N1 | 0.0630 (10) | 0.0672 (11) | 0.0587 (11) | 0.0002 (9) | −0.0003 (8) | 0.0062 (9) |
N2 | 0.0791 (13) | 0.0771 (13) | 0.0622 (11) | −0.0129 (11) | 0.0077 (10) | −0.0152 (10) |
N3 | 0.0491 (8) | 0.0545 (9) | 0.0616 (9) | 0.0023 (7) | 0.0010 (7) | 0.0064 (7) |
C1 | 0.0460 (9) | 0.0463 (9) | 0.0522 (10) | −0.0056 (8) | −0.0047 (8) | −0.0057 (8) |
C2 | 0.0597 (12) | 0.0656 (12) | 0.0476 (11) | 0.0055 (10) | 0.0022 (9) | −0.0112 (9) |
C3 | 0.0554 (12) | 0.0552 (11) | 0.0618 (12) | 0.0094 (10) | 0.0029 (9) | −0.0059 (10) |
C4 | 0.0486 (10) | 0.0468 (9) | 0.0507 (10) | −0.0043 (8) | 0.0002 (8) | 0.0005 (8) |
C5 | 0.0616 (12) | 0.0606 (12) | 0.0501 (11) | 0.0023 (10) | 0.0048 (9) | −0.0099 (9) |
C6 | 0.0565 (12) | 0.0537 (11) | 0.0615 (12) | 0.0089 (9) | 0.0018 (9) | −0.0094 (9) |
C7 | 0.0449 (9) | 0.0527 (10) | 0.0482 (10) | 0.0054 (8) | −0.0002 (8) | −0.0061 (8) |
C8 | 0.0597 (11) | 0.0617 (12) | 0.0582 (12) | 0.0113 (10) | −0.0136 (10) | −0.0001 (10) |
C9 | 0.0697 (13) | 0.0496 (12) | 0.0690 (13) | 0.0098 (10) | −0.0051 (11) | −0.0018 (10) |
C10 | 0.0537 (10) | 0.0596 (11) | 0.0458 (10) | −0.0019 (9) | 0.0041 (8) | −0.0088 (9) |
C11 | 0.0748 (14) | 0.0700 (14) | 0.0478 (11) | 0.0025 (11) | −0.0151 (10) | −0.0012 (10) |
C12 | 0.0786 (14) | 0.0554 (12) | 0.0582 (12) | 0.0067 (11) | −0.0153 (11) | 0.0032 (10) |
C13 | 0.0621 (13) | 0.0686 (15) | 0.0733 (16) | 0.0121 (12) | −0.0161 (12) | −0.0067 (12) |
C14 | 0.0800 (19) | 0.095 (2) | 0.104 (2) | −0.0102 (16) | 0.0121 (17) | 0.0388 (18) |
P1—O7 | 1.4547 (14) | C4—C5 | 1.370 (3) |
P1—O1 | 1.5845 (13) | C5—C6 | 1.375 (3) |
P1—O4 | 1.5999 (14) | C5—H5 | 0.94 (2) |
P1—N3 | 1.6032 (17) | C6—H6 | 0.94 (2) |
O1—C1 | 1.403 (2) | C7—C8 | 1.371 (3) |
O2—N1 | 1.211 (2) | C7—C12 | 1.376 (3) |
O3—N1 | 1.218 (2) | C8—C9 | 1.374 (3) |
O4—C7 | 1.393 (2) | C8—H8 | 0.95 (3) |
O5—N2 | 1.220 (3) | C9—C10 | 1.370 (3) |
O6—N2 | 1.220 (3) | C9—H9 | 0.90 (2) |
N1—C4 | 1.475 (2) | C10—C11 | 1.368 (3) |
N2—C10 | 1.465 (3) | C11—C12 | 1.377 (3) |
N3—C14 | 1.460 (3) | C11—H11 | 0.94 (3) |
N3—C13 | 1.461 (3) | C12—H12 | 0.93 (2) |
C1—C6 | 1.370 (3) | C13—H13A | 0.96 (2) |
C1—C2 | 1.379 (3) | C13—H13B | 1.00 (3) |
C2—C3 | 1.369 (3) | C13—H13C | 0.95 (3) |
C2—H2 | 0.89 (2) | C14—H14A | 0.97 (3) |
C3—C4 | 1.370 (3) | C14—H14B | 1.08 (3) |
C3—H3 | 0.90 (2) | C14—H14C | 1.00 (3) |
O7—P1—O1 | 115.81 (8) | C1—C6—H6 | 116.4 (14) |
O7—P1—O4 | 113.65 (8) | C5—C6—H6 | 123.9 (14) |
O1—P1—O4 | 98.49 (7) | C8—C7—C12 | 121.39 (19) |
O7—P1—N3 | 115.77 (8) | C8—C7—O4 | 117.51 (16) |
O1—P1—N3 | 104.53 (8) | C12—C7—O4 | 121.09 (17) |
O4—P1—N3 | 106.75 (9) | C7—C8—C9 | 119.13 (19) |
C1—O1—P1 | 123.38 (11) | C7—C8—H8 | 120.7 (14) |
C7—O4—P1 | 120.95 (11) | C9—C8—H8 | 120.2 (14) |
O2—N1—O3 | 123.73 (19) | C10—C9—C8 | 119.2 (2) |
O2—N1—C4 | 118.60 (18) | C10—C9—H9 | 119.8 (15) |
O3—N1—C4 | 117.66 (18) | C8—C9—H9 | 120.8 (15) |
O6—N2—O5 | 123.2 (2) | C11—C10—C9 | 122.15 (19) |
O6—N2—C10 | 118.2 (2) | C11—C10—N2 | 118.66 (18) |
O5—N2—C10 | 118.6 (2) | C9—C10—N2 | 119.19 (19) |
C14—N3—C13 | 114.6 (2) | C10—C11—C12 | 118.58 (19) |
C14—N3—P1 | 121.70 (17) | C10—C11—H11 | 121.1 (16) |
C13—N3—P1 | 121.99 (17) | C12—C11—H11 | 120.3 (16) |
C6—C1—C2 | 121.57 (18) | C7—C12—C11 | 119.5 (2) |
C6—C1—O1 | 117.60 (16) | C7—C12—H12 | 120.8 (14) |
C2—C1—O1 | 120.73 (17) | C11—C12—H12 | 119.5 (14) |
C3—C2—C1 | 118.98 (19) | N3—C13—H13A | 105.7 (14) |
C3—C2—H2 | 118.7 (14) | N3—C13—H13B | 111.1 (16) |
C1—C2—H2 | 122.3 (14) | H13A—C13—H13B | 110 (2) |
C2—C3—C4 | 119.10 (19) | N3—C13—H13C | 106.8 (17) |
C2—C3—H3 | 123.4 (15) | H13A—C13—H13C | 112 (2) |
C4—C3—H3 | 117.5 (15) | H13B—C13—H13C | 111 (2) |
C3—C4—C5 | 122.33 (18) | N3—C14—H14A | 114.2 (18) |
C3—C4—N1 | 119.22 (18) | N3—C14—H14B | 111.4 (19) |
C5—C4—N1 | 118.45 (18) | H14A—C14—H14B | 99 (3) |
C4—C5—C6 | 118.51 (19) | N3—C14—H14C | 109.9 (18) |
C4—C5—H5 | 122.4 (13) | H14A—C14—H14C | 116 (3) |
C6—C5—H5 | 119.0 (13) | H14B—C14—H14C | 106 (3) |
C1—C6—C5 | 119.48 (19) | ||
O7—P1—O1—C1 | 47.65 (16) | O3—N1—C4—C5 | 176.33 (19) |
O4—P1—O1—C1 | −73.86 (15) | C3—C4—C5—C6 | −1.1 (3) |
N3—P1—O1—C1 | 176.28 (14) | N1—C4—C5—C6 | 179.16 (17) |
O7—P1—O4—C7 | 45.88 (16) | C2—C1—C6—C5 | 1.3 (3) |
O1—P1—O4—C7 | 168.97 (13) | O1—C1—C6—C5 | −175.02 (17) |
N3—P1—O4—C7 | −82.98 (15) | C4—C5—C6—C1 | −0.3 (3) |
O7—P1—N3—C14 | −177.6 (2) | P1—O4—C7—C8 | −119.59 (18) |
O1—P1—N3—C14 | 53.7 (2) | P1—O4—C7—C12 | 61.6 (2) |
O4—P1—N3—C14 | −50.0 (2) | C12—C7—C8—C9 | 0.9 (3) |
O7—P1—N3—C13 | 18.0 (2) | O4—C7—C8—C9 | −177.98 (18) |
O1—P1—N3—C13 | −110.61 (17) | C7—C8—C9—C10 | −0.1 (3) |
O4—P1—N3—C13 | 145.67 (17) | C8—C9—C10—C11 | −0.9 (3) |
P1—O1—C1—C6 | −106.60 (18) | C8—C9—C10—N2 | 178.77 (19) |
P1—O1—C1—C2 | 77.0 (2) | O6—N2—C10—C11 | −7.1 (3) |
C6—C1—C2—C3 | −1.0 (3) | O5—N2—C10—C11 | 173.5 (2) |
O1—C1—C2—C3 | 175.28 (17) | O6—N2—C10—C9 | 173.2 (2) |
C1—C2—C3—C4 | −0.4 (3) | O5—N2—C10—C9 | −6.2 (3) |
C2—C3—C4—C5 | 1.5 (3) | C9—C10—C11—C12 | 1.1 (3) |
C2—C3—C4—N1 | −178.79 (18) | N2—C10—C11—C12 | −178.6 (2) |
O2—N1—C4—C3 | 175.4 (2) | C8—C7—C12—C11 | −0.7 (3) |
O3—N1—C4—C3 | −3.4 (3) | O4—C7—C12—C11 | 178.14 (19) |
O2—N1—C4—C5 | −4.9 (3) | C10—C11—C12—C7 | −0.3 (3) |
Experimental details
Crystal data | |
Chemical formula | C14H14N3O7P |
Mr | 367.25 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 298 |
a, b, c (Å) | 9.139 (2), 11.083 (2), 16.411 (3) |
β (°) | 95.838 (2) |
V (Å3) | 1653.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.65 × 0.18 × 0.18 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Empirical (using intensity measurements) via ψ scan (North et al., 1968) |
Tmin, Tmax | 0.898, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5105, 4823, 2557 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.134, 0.92 |
No. of reflections | 4823 |
No. of parameters | 282 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.21, −0.26 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1989), CAD-4 EXPRESS, NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
P1—O7 | 1.4547 (14) | P1—O4 | 1.5999 (14) |
P1—O1 | 1.5845 (13) | P1—N3 | 1.6032 (17) |
O7—P1—O1 | 115.81 (8) | O7—P1—N3 | 115.77 (8) |
O7—P1—O4 | 113.65 (8) | O1—P1—N3 | 104.53 (8) |
O1—P1—O4 | 98.49 (7) | O4—P1—N3 | 106.75 (9) |
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The title compound, (I), which acts as an inhibitor of blood coagulation (De Lange & Hemker, 1972), has been characterized by mass spectrometry (Meyer et al., 1978). It possesses a nitro substituent in the para position of the aromatic ring; the presence of two nitrophenyl entities considerably shortens the P—N bond [1.6032 (17) Å], which is significantly shorter than the corresponding distance (1.77 Å) found in NaHPO3(NH2), but is much longer than that (1.57 Å) found in (C6H5)3PN (Corbridge, 1995). On the basis of the P—N distance, the P—N bond in (I) is expected to display double-bond character. The double-bond character is also shown by the sum of the angles at the N atom of almost 360°.