organic compounds
N-(4-Fluorobenzoyl)-N′,N′′-diisopropylphosphoric triamide
aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
*Correspondence e-mail: pourayoubi@um.ac.ir
The 13H21FN3O2P, consists of two independent molecules. In each molecule, the P=O group and the N—H unit belonging to the C(O)NHP(O) fragment are in a syn conformation with respect to each other. An intramolecular N—H⋯O hydrogen bond occurs in each molecule. The P atom adopts a distorted tetrahedral environment. The methyl groups of an isopropyl fragment are disordered over two sets of sites with refined occupancies of 0.458 (5) and 0.542 (5). In the crystal, molecules are linked through N—H⋯O(=P) and N—H⋯O(=C) hydrogen bonds into chains along [001].
of the title phosphoric triamide, CRelated literature
For related structures with a [C(O)NH]P(O)[NHC]2 moiety, see: Pourayoubi et al. (2011); Raissi Shabari et al. (2012). For the preparation of the starting compound 4-F—C6H4C(O)NHP(O)Cl2, see: Tarahhomi et al. (2011).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004).
Supporting information
10.1107/S1600536812046326/ff2089sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046326/ff2089Isup2.hkl
4-F—C6H4C(O)NHP(O)Cl2 was prepared according to the literature method reported by Tarahhomi et al. (2011).
To a solution of 4-F—C6H4C(O)NHP(O)Cl2 (1 mmol) in chloroform (25 ml), a solution of isopropylamine (4 mmol) in chloroform (5 ml) was added at 273 K. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from a mixture of CH3OH/DMF (5:1 v/v) at room temperature.
All non-hydrogen atoms refined anisotropically by full matrix least squares on F2. Disorder with respect to the methyl carbon atoms C12 and C13 of an isopropyl group was treated using a two part model (45.8/54.2) with restrained C—C distances of 1.55 (0.02) Å. Hydrogen atoms H1N, H2N, H3N, H4N, H5N, and H6N were found from a Fourier difference map and were refined isotropically with N—H distances of 0.87 (2) Å and 1.20 Ueq of parent N atom. All other hydrogen atoms were placed in calculated positions with C—H distances of (C—HAr) 0.95 Å, (C—H) 1.00 Å, (CH3) 0.98 Å and Ueq of 1.20 and 1.50 of parent C atom.
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).Fig. 1. An ORTEP-style plot and atom labeling scheme for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii. | |
Fig. 2. Part of the crystal packing of the title compound via the N—H···O hydrogen bonds parallel to [001], building R22(8) and R22(12) rings. The intermolecular hydrogen bonds are shown as dotted lines and the H atoms not involved in hydrogen bonding have been omitted for the sake of clarity. The CH(CH3)2 substituents are shown as balls. The intramolecular N—H···O hydrogen bonds are not shown. |
C13H21FN3O2P | F(000) = 1280 |
Mr = 301.30 | Dx = 1.280 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.9974 (12) Å | Cell parameters from 6765 reflections |
b = 10.7474 (7) Å | θ = 2.7–26.4° |
c = 19.5478 (13) Å | µ = 0.19 mm−1 |
β = 111.461 (2)° | T = 100 K |
V = 3127.8 (4) Å3 | Block, colourless |
Z = 8 | 0.22 × 0.20 × 0.15 mm |
Bruker APEXII CCD diffractometer | 6366 independent reflections |
Radiation source: fine-focus sealed tube | 4979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 26.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −20→19 |
Tmin = 0.959, Tmax = 0.972 | k = −12→13 |
24038 measured reflections | l = −24→24 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0604P)2 + 3.5857P] where P = (Fo2 + 2Fc2)/3 |
6366 reflections | (Δ/σ)max = 0.024 |
385 parameters | Δρmax = 1.28 e Å−3 |
11 restraints | Δρmin = −1.25 e Å−3 |
C13H21FN3O2P | V = 3127.8 (4) Å3 |
Mr = 301.30 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.9974 (12) Å | µ = 0.19 mm−1 |
b = 10.7474 (7) Å | T = 100 K |
c = 19.5478 (13) Å | 0.22 × 0.20 × 0.15 mm |
β = 111.461 (2)° |
Bruker APEXII CCD diffractometer | 6366 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 4979 reflections with I > 2σ(I) |
Tmin = 0.959, Tmax = 0.972 | Rint = 0.035 |
24038 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 11 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.28 e Å−3 |
6366 reflections | Δρmin = −1.25 e Å−3 |
385 parameters |
Experimental. IR (KBr, ν, cm-1): 3345, 3095, 2972, 1657, 1452, 1291, 1215, 1139, 1025, 887, 769, 683. |
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 | Occ. (<1) | |
P1 | 0.66641 (4) | 0.16703 (5) | 0.60938 (3) | 0.01446 (15) | |
P2 | 0.21362 (4) | 0.66868 (5) | 0.64779 (3) | 0.01601 (15) | |
F1 | 1.19973 (10) | 0.26579 (16) | 0.81566 (8) | 0.0353 (4) | |
F2 | 0.75090 (10) | 0.72695 (16) | 0.81958 (8) | 0.0346 (4) | |
O1 | 0.81182 (11) | 0.27790 (16) | 0.57067 (9) | 0.0233 (4) | |
O2 | 0.62755 (10) | 0.11428 (15) | 0.66103 (8) | 0.0184 (3) | |
O3 | 0.34880 (12) | 0.81368 (16) | 0.60767 (9) | 0.0257 (4) | |
O4 | 0.18241 (11) | 0.59057 (15) | 0.69603 (8) | 0.0191 (3) | |
N1 | 0.77938 (13) | 0.17148 (18) | 0.65776 (10) | 0.0167 (4) | |
H1N | 0.7967 (17) | 0.148 (2) | 0.7034 (10) | 0.020* | |
N2 | 0.64876 (13) | 0.08672 (17) | 0.53551 (10) | 0.0163 (4) | |
H2N | 0.6444 (17) | 0.124 (2) | 0.4962 (11) | 0.020* | |
N3 | 0.63066 (14) | 0.30688 (18) | 0.58047 (11) | 0.0199 (4) | |
H3N | 0.6526 (18) | 0.333 (2) | 0.5509 (13) | 0.024* | |
N4 | 0.32492 (13) | 0.69042 (18) | 0.69250 (10) | 0.0182 (4) | |
H4N | 0.3451 (17) | 0.668 (2) | 0.7372 (10) | 0.022* | |
N5 | 0.19346 (14) | 0.60247 (18) | 0.56892 (10) | 0.0190 (4) | |
H5N | 0.1955 (18) | 0.647 (2) | 0.5336 (12) | 0.023* | |
N6 | 0.17165 (14) | 0.80866 (19) | 0.63345 (11) | 0.0225 (4) | |
H6N | 0.2011 (18) | 0.861 (2) | 0.6202 (15) | 0.027* | |
C1 | 0.98985 (16) | 0.3212 (2) | 0.66618 (13) | 0.0214 (5) | |
H1B | 0.9655 | 0.3738 | 0.6245 | 0.026* | |
C2 | 1.07965 (17) | 0.3330 (2) | 0.71090 (14) | 0.0239 (5) | |
H2C | 1.1172 | 0.3931 | 0.7009 | 0.029* | |
C3 | 1.11214 (16) | 0.2545 (2) | 0.77028 (13) | 0.0240 (5) | |
C4 | 1.06095 (17) | 0.1645 (2) | 0.78636 (13) | 0.0248 (5) | |
H4C | 1.0865 | 0.1105 | 0.8272 | 0.030* | |
C5 | 0.97113 (16) | 0.1547 (2) | 0.74148 (12) | 0.0204 (5) | |
H5B | 0.9343 | 0.0940 | 0.7519 | 0.024* | |
C6 | 0.93470 (15) | 0.2335 (2) | 0.68126 (12) | 0.0163 (4) | |
C7 | 0.83791 (15) | 0.2292 (2) | 0.63192 (12) | 0.0174 (5) | |
C8 | 0.67839 (16) | −0.0441 (2) | 0.54144 (13) | 0.0216 (5) | |
H8A | 0.6991 | −0.0683 | 0.5944 | 0.026* | |
C9 | 0.75718 (18) | −0.0592 (3) | 0.51657 (15) | 0.0314 (6) | |
H9A | 0.8062 | −0.0041 | 0.5455 | 0.047* | |
H9B | 0.7384 | −0.0377 | 0.4644 | 0.047* | |
H9C | 0.7779 | −0.1458 | 0.5238 | 0.047* | |
C10 | 0.59970 (19) | −0.1273 (3) | 0.49919 (16) | 0.0339 (6) | |
H10A | 0.5511 | −0.1153 | 0.5178 | 0.051* | |
H10B | 0.6190 | −0.2145 | 0.5057 | 0.051* | |
H10C | 0.5782 | −0.1059 | 0.4469 | 0.051* | |
C11 | 0.62386 (19) | 0.4006 (2) | 0.63394 (14) | 0.0293 (6) | |
H11A | 0.6168 | 0.4687 | 0.5974 | 0.044* | 0.458 (5) |
H11B | 0.6167 | 0.3669 | 0.6792 | 0.044* | 0.542 (5) |
C12 | 0.7119 (6) | 0.4539 (9) | 0.6829 (5) | 0.0619 (11) | 0.458 (5) |
H12A | 0.7376 | 0.4014 | 0.7266 | 0.093* | 0.458 (5) |
H12B | 0.7026 | 0.5382 | 0.6978 | 0.093* | 0.458 (5) |
H12C | 0.7532 | 0.4570 | 0.6562 | 0.093* | 0.458 (5) |
C13 | 0.5276 (6) | 0.4168 (8) | 0.6273 (5) | 0.0619 (11) | 0.458 (5) |
H13A | 0.4995 | 0.3349 | 0.6244 | 0.093* | 0.458 (5) |
H13B | 0.4948 | 0.4644 | 0.5828 | 0.093* | 0.458 (5) |
H13C | 0.5258 | 0.4615 | 0.6704 | 0.093* | 0.458 (5) |
C12' | 0.6977 (5) | 0.5009 (7) | 0.6466 (5) | 0.0619 (11) | 0.542 (5) |
H12D | 0.7565 | 0.4650 | 0.6752 | 0.093* | 0.542 (5) |
H12E | 0.6857 | 0.5712 | 0.6736 | 0.093* | 0.542 (5) |
H12F | 0.6977 | 0.5299 | 0.5991 | 0.093* | 0.542 (5) |
C13' | 0.5514 (5) | 0.4973 (6) | 0.5888 (4) | 0.0619 (11) | 0.542 (5) |
H13D | 0.4917 | 0.4590 | 0.5731 | 0.093* | 0.542 (5) |
H13E | 0.5639 | 0.5235 | 0.5455 | 0.093* | 0.542 (5) |
H13F | 0.5532 | 0.5700 | 0.6196 | 0.093* | 0.542 (5) |
C14 | 0.53551 (17) | 0.8319 (2) | 0.69340 (13) | 0.0209 (5) | |
H14A | 0.5109 | 0.8941 | 0.6570 | 0.025* | |
C15 | 0.62753 (17) | 0.8276 (2) | 0.73154 (14) | 0.0245 (5) | |
H15A | 0.6664 | 0.8872 | 0.7229 | 0.029* | |
C16 | 0.66076 (16) | 0.7340 (2) | 0.78238 (13) | 0.0241 (5) | |
C17 | 0.60747 (17) | 0.6462 (2) | 0.79746 (13) | 0.0248 (5) | |
H17A | 0.6330 | 0.5823 | 0.8325 | 0.030* | |
C18 | 0.51529 (16) | 0.6533 (2) | 0.75999 (13) | 0.0227 (5) | |
H18A | 0.4770 | 0.5946 | 0.7701 | 0.027* | |
C19 | 0.47844 (16) | 0.7459 (2) | 0.70771 (12) | 0.0179 (5) | |
C20 | 0.37995 (16) | 0.7536 (2) | 0.66527 (12) | 0.0186 (5) | |
C21 | 0.20729 (17) | 0.4683 (2) | 0.56179 (13) | 0.0232 (5) | |
H21A | 0.2013 | 0.4257 | 0.6053 | 0.028* | |
C22 | 0.2994 (2) | 0.4408 (3) | 0.5623 (2) | 0.0550 (9) | |
H22A | 0.3444 | 0.4811 | 0.6049 | 0.082* | |
H22B | 0.3046 | 0.4728 | 0.5171 | 0.082* | |
H22C | 0.3093 | 0.3507 | 0.5652 | 0.082* | |
C23 | 0.1340 (3) | 0.4201 (3) | 0.4942 (2) | 0.0723 (14) | |
H23A | 0.0754 | 0.4378 | 0.4974 | 0.108* | |
H23B | 0.1409 | 0.3300 | 0.4904 | 0.108* | |
H23C | 0.1378 | 0.4610 | 0.4506 | 0.108* | |
C24 | 0.07352 (18) | 0.8274 (2) | 0.60296 (14) | 0.0277 (6) | |
H24A | 0.0453 | 0.7512 | 0.6145 | 0.033* | |
C25 | 0.0378 (2) | 0.8417 (3) | 0.52048 (15) | 0.0354 (7) | |
H25A | 0.0521 | 0.7670 | 0.4982 | 0.053* | |
H25B | 0.0655 | 0.9145 | 0.5072 | 0.053* | |
H25C | −0.0275 | 0.8529 | 0.5025 | 0.053* | |
C26 | 0.0489 (2) | 0.9359 (3) | 0.64109 (16) | 0.0430 (8) | |
H26A | 0.0694 | 0.9193 | 0.6940 | 0.064* | |
H26B | −0.0165 | 0.9470 | 0.6214 | 0.064* | |
H26C | 0.0777 | 1.0117 | 0.6326 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0147 (3) | 0.0187 (3) | 0.0103 (3) | −0.0003 (2) | 0.0049 (2) | −0.0013 (2) |
P2 | 0.0177 (3) | 0.0191 (3) | 0.0117 (3) | 0.0005 (2) | 0.0059 (2) | 0.0002 (2) |
F1 | 0.0164 (8) | 0.0524 (10) | 0.0328 (8) | −0.0072 (7) | 0.0038 (6) | −0.0086 (7) |
F2 | 0.0178 (8) | 0.0483 (10) | 0.0357 (9) | −0.0050 (7) | 0.0076 (6) | −0.0064 (7) |
O1 | 0.0236 (9) | 0.0325 (9) | 0.0150 (8) | −0.0006 (7) | 0.0085 (7) | 0.0053 (7) |
O2 | 0.0179 (8) | 0.0257 (8) | 0.0128 (7) | −0.0031 (7) | 0.0070 (6) | −0.0031 (6) |
O3 | 0.0286 (10) | 0.0303 (9) | 0.0171 (8) | −0.0017 (7) | 0.0072 (7) | 0.0081 (7) |
O4 | 0.0197 (9) | 0.0259 (9) | 0.0128 (7) | −0.0032 (7) | 0.0070 (6) | −0.0004 (6) |
N1 | 0.0157 (10) | 0.0243 (10) | 0.0096 (8) | −0.0030 (8) | 0.0039 (7) | 0.0006 (7) |
N2 | 0.0196 (10) | 0.0201 (10) | 0.0086 (8) | 0.0011 (8) | 0.0044 (7) | 0.0010 (7) |
N3 | 0.0234 (11) | 0.0206 (10) | 0.0172 (10) | 0.0028 (8) | 0.0093 (8) | 0.0005 (8) |
N4 | 0.0191 (10) | 0.0253 (10) | 0.0097 (9) | −0.0015 (8) | 0.0047 (7) | 0.0034 (7) |
N5 | 0.0265 (11) | 0.0193 (10) | 0.0123 (9) | 0.0025 (8) | 0.0084 (8) | 0.0021 (7) |
N6 | 0.0251 (12) | 0.0198 (10) | 0.0228 (10) | 0.0026 (8) | 0.0091 (9) | −0.0005 (8) |
C1 | 0.0225 (13) | 0.0202 (12) | 0.0264 (12) | 0.0010 (9) | 0.0146 (10) | 0.0008 (9) |
C2 | 0.0213 (13) | 0.0214 (12) | 0.0341 (14) | −0.0048 (10) | 0.0163 (11) | −0.0051 (10) |
C3 | 0.0148 (12) | 0.0341 (14) | 0.0235 (12) | −0.0031 (10) | 0.0076 (9) | −0.0100 (10) |
C4 | 0.0206 (13) | 0.0354 (14) | 0.0178 (11) | 0.0021 (11) | 0.0063 (10) | 0.0037 (10) |
C5 | 0.0179 (12) | 0.0259 (12) | 0.0187 (11) | −0.0023 (9) | 0.0082 (9) | 0.0013 (9) |
C6 | 0.0159 (11) | 0.0201 (11) | 0.0147 (10) | −0.0008 (9) | 0.0079 (9) | −0.0025 (8) |
C7 | 0.0201 (12) | 0.0192 (11) | 0.0152 (11) | −0.0008 (9) | 0.0089 (9) | −0.0007 (9) |
C8 | 0.0252 (13) | 0.0219 (12) | 0.0169 (11) | 0.0032 (10) | 0.0067 (9) | −0.0015 (9) |
C9 | 0.0239 (14) | 0.0318 (14) | 0.0384 (15) | 0.0035 (11) | 0.0112 (12) | −0.0096 (12) |
C10 | 0.0354 (16) | 0.0271 (14) | 0.0448 (17) | −0.0065 (12) | 0.0215 (13) | −0.0123 (12) |
C11 | 0.0413 (16) | 0.0229 (13) | 0.0277 (13) | 0.0037 (11) | 0.0173 (12) | −0.0055 (10) |
C12 | 0.083 (3) | 0.046 (2) | 0.070 (3) | −0.003 (2) | 0.044 (2) | −0.0214 (19) |
C13 | 0.083 (3) | 0.046 (2) | 0.070 (3) | −0.003 (2) | 0.044 (2) | −0.0214 (19) |
C12' | 0.083 (3) | 0.046 (2) | 0.070 (3) | −0.003 (2) | 0.044 (2) | −0.0214 (19) |
C13' | 0.083 (3) | 0.046 (2) | 0.070 (3) | −0.003 (2) | 0.044 (2) | −0.0214 (19) |
C14 | 0.0285 (13) | 0.0173 (11) | 0.0218 (12) | −0.0018 (10) | 0.0151 (10) | −0.0013 (9) |
C15 | 0.0243 (13) | 0.0227 (12) | 0.0329 (13) | −0.0075 (10) | 0.0179 (11) | −0.0054 (10) |
C16 | 0.0173 (12) | 0.0326 (13) | 0.0232 (12) | −0.0034 (10) | 0.0082 (10) | −0.0093 (10) |
C17 | 0.0234 (13) | 0.0334 (14) | 0.0185 (11) | 0.0007 (10) | 0.0088 (10) | 0.0034 (10) |
C18 | 0.0214 (13) | 0.0295 (13) | 0.0183 (11) | −0.0033 (10) | 0.0085 (10) | 0.0041 (10) |
C19 | 0.0225 (12) | 0.0200 (11) | 0.0139 (10) | −0.0019 (9) | 0.0099 (9) | −0.0023 (8) |
C20 | 0.0242 (13) | 0.0186 (11) | 0.0140 (10) | −0.0005 (9) | 0.0081 (9) | −0.0002 (9) |
C21 | 0.0321 (14) | 0.0202 (12) | 0.0188 (11) | 0.0048 (10) | 0.0111 (10) | −0.0010 (9) |
C22 | 0.053 (2) | 0.0428 (19) | 0.080 (3) | 0.0130 (16) | 0.037 (2) | −0.0067 (18) |
C23 | 0.061 (2) | 0.0353 (18) | 0.087 (3) | 0.0087 (17) | −0.013 (2) | −0.0311 (19) |
C24 | 0.0289 (14) | 0.0278 (13) | 0.0281 (13) | 0.0090 (11) | 0.0124 (11) | 0.0041 (10) |
C25 | 0.0352 (16) | 0.0377 (15) | 0.0277 (14) | 0.0128 (12) | 0.0048 (12) | 0.0006 (12) |
C26 | 0.053 (2) | 0.0476 (18) | 0.0314 (15) | 0.0243 (15) | 0.0183 (14) | 0.0018 (13) |
P1—O2 | 1.4788 (16) | C11—C12' | 1.551 (7) |
P1—N2 | 1.6159 (18) | C11—C13' | 1.567 (7) |
P1—N3 | 1.634 (2) | C11—H11A | 1.0000 |
P1—N1 | 1.7065 (19) | C11—H11B | 1.0000 |
P2—O4 | 1.4792 (16) | C12—H12A | 0.9800 |
P2—N5 | 1.6197 (19) | C12—H12B | 0.9800 |
P2—N6 | 1.629 (2) | C12—H12C | 0.9800 |
P2—N4 | 1.688 (2) | C13—H13A | 0.9800 |
F1—C3 | 1.362 (3) | C13—H13B | 0.9800 |
F2—C16 | 1.359 (3) | C13—H13C | 0.9800 |
O1—C7 | 1.231 (3) | C12'—H12D | 0.9800 |
O3—C20 | 1.234 (3) | C12'—H12E | 0.9800 |
N1—C7 | 1.365 (3) | C12'—H12F | 0.9800 |
N1—H1N | 0.868 (16) | C13'—H13D | 0.9800 |
N2—C8 | 1.475 (3) | C13'—H13E | 0.9800 |
N2—H2N | 0.848 (16) | C13'—H13F | 0.9800 |
N3—C11 | 1.484 (3) | C14—C15 | 1.386 (4) |
N3—H3N | 0.828 (17) | C14—C19 | 1.397 (3) |
N4—C20 | 1.364 (3) | C14—H14A | 0.9500 |
N4—H4N | 0.849 (17) | C15—C16 | 1.377 (4) |
N5—C21 | 1.473 (3) | C15—H15A | 0.9500 |
N5—H5N | 0.852 (17) | C16—C17 | 1.374 (4) |
N6—C24 | 1.475 (3) | C17—C18 | 1.388 (3) |
N6—H6N | 0.833 (17) | C17—H17A | 0.9500 |
C1—C2 | 1.388 (3) | C18—C19 | 1.393 (3) |
C1—C6 | 1.395 (3) | C18—H18A | 0.9500 |
C1—H1B | 0.9500 | C19—C20 | 1.490 (3) |
C2—C3 | 1.374 (4) | C21—C22 | 1.498 (4) |
C2—H2C | 0.9500 | C21—C23 | 1.502 (4) |
C3—C4 | 1.375 (4) | C21—H21A | 1.0000 |
C4—C5 | 1.387 (3) | C22—H22A | 0.9800 |
C4—H4C | 0.9500 | C22—H22B | 0.9800 |
C5—C6 | 1.393 (3) | C22—H22C | 0.9800 |
C5—H5B | 0.9500 | C23—H23A | 0.9800 |
C6—C7 | 1.496 (3) | C23—H23B | 0.9800 |
C8—C9 | 1.516 (4) | C23—H23C | 0.9800 |
C8—C10 | 1.519 (4) | C24—C25 | 1.509 (4) |
C8—H8A | 1.0000 | C24—C26 | 1.512 (4) |
C9—H9A | 0.9800 | C24—H24A | 1.0000 |
C9—H9B | 0.9800 | C25—H25A | 0.9800 |
C9—H9C | 0.9800 | C25—H25B | 0.9800 |
C10—H10A | 0.9800 | C25—H25C | 0.9800 |
C10—H10B | 0.9800 | C26—H26A | 0.9800 |
C10—H10C | 0.9800 | C26—H26B | 0.9800 |
C11—C12 | 1.497 (9) | C26—H26C | 0.9800 |
C11—C13 | 1.508 (8) | ||
O2—P1—N2 | 115.19 (10) | C13—C11—H11B | 71.0 |
O2—P1—N3 | 114.04 (10) | C12'—C11—H11B | 116.0 |
N2—P1—N3 | 104.94 (10) | C13'—C11—H11B | 116.0 |
O2—P1—N1 | 104.88 (9) | H11A—C11—H11B | 151.4 |
N2—P1—N1 | 108.28 (10) | C11—C12—H12A | 109.5 |
N3—P1—N1 | 109.37 (10) | C11—C12—H12B | 109.5 |
O4—P2—N5 | 111.19 (10) | H12A—C12—H12B | 109.5 |
O4—P2—N6 | 114.82 (10) | C11—C12—H12C | 109.5 |
N5—P2—N6 | 108.42 (10) | H12A—C12—H12C | 109.5 |
O4—P2—N4 | 106.65 (9) | H12B—C12—H12C | 109.5 |
N5—P2—N4 | 111.01 (10) | C11—C13—H13A | 109.5 |
N6—P2—N4 | 104.57 (11) | C11—C13—H13B | 109.5 |
C7—N1—P1 | 122.57 (16) | H13A—C13—H13B | 109.5 |
C7—N1—H1N | 120.4 (17) | C11—C13—H13C | 109.5 |
P1—N1—H1N | 115.9 (17) | H13A—C13—H13C | 109.5 |
C8—N2—P1 | 119.54 (15) | H13B—C13—H13C | 109.5 |
C8—N2—H2N | 116.2 (18) | C11—C12'—H12D | 109.5 |
P1—N2—H2N | 119.1 (18) | C11—C12'—H12E | 109.5 |
C11—N3—P1 | 119.18 (16) | H12D—C12'—H12E | 109.5 |
C11—N3—H3N | 114.6 (19) | C11—C12'—H12F | 109.5 |
P1—N3—H3N | 112.0 (19) | H12D—C12'—H12F | 109.5 |
C20—N4—P2 | 125.15 (16) | H12E—C12'—H12F | 109.5 |
C20—N4—H4N | 119.2 (18) | C11—C13'—H13D | 109.5 |
P2—N4—H4N | 115.2 (18) | C11—C13'—H13E | 109.5 |
C21—N5—P2 | 122.39 (16) | H13D—C13'—H13E | 109.5 |
C21—N5—H5N | 115.1 (18) | C11—C13'—H13F | 109.5 |
P2—N5—H5N | 118.0 (18) | H13D—C13'—H13F | 109.5 |
C24—N6—P2 | 120.41 (17) | H13E—C13'—H13F | 109.5 |
C24—N6—H6N | 115 (2) | C15—C14—C19 | 120.9 (2) |
P2—N6—H6N | 116 (2) | C15—C14—H14A | 119.6 |
C2—C1—C6 | 121.2 (2) | C19—C14—H14A | 119.6 |
C2—C1—H1B | 119.4 | C16—C15—C14 | 117.8 (2) |
C6—C1—H1B | 119.4 | C16—C15—H15A | 121.1 |
C3—C2—C1 | 117.4 (2) | C14—C15—H15A | 121.1 |
C3—C2—H2C | 121.3 | F2—C16—C17 | 117.8 (2) |
C1—C2—H2C | 121.3 | F2—C16—C15 | 118.7 (2) |
F1—C3—C2 | 118.4 (2) | C17—C16—C15 | 123.4 (2) |
F1—C3—C4 | 118.1 (2) | C16—C17—C18 | 118.1 (2) |
C2—C3—C4 | 123.5 (2) | C16—C17—H17A | 120.9 |
C3—C4—C5 | 118.3 (2) | C18—C17—H17A | 120.9 |
C3—C4—H4C | 120.8 | C17—C18—C19 | 120.6 (2) |
C5—C4—H4C | 120.8 | C17—C18—H18A | 119.7 |
C4—C5—C6 | 120.3 (2) | C19—C18—H18A | 119.7 |
C4—C5—H5B | 119.8 | C18—C19—C14 | 119.1 (2) |
C6—C5—H5B | 119.8 | C18—C19—C20 | 121.7 (2) |
C5—C6—C1 | 119.2 (2) | C14—C19—C20 | 119.2 (2) |
C5—C6—C7 | 122.7 (2) | O3—C20—N4 | 120.9 (2) |
C1—C6—C7 | 118.0 (2) | O3—C20—C19 | 121.9 (2) |
O1—C7—N1 | 121.2 (2) | N4—C20—C19 | 117.19 (19) |
O1—C7—C6 | 121.1 (2) | N5—C21—C22 | 111.9 (2) |
N1—C7—C6 | 117.63 (19) | N5—C21—C23 | 109.0 (2) |
N2—C8—C9 | 111.0 (2) | C22—C21—C23 | 112.8 (3) |
N2—C8—C10 | 109.9 (2) | N5—C21—H21A | 107.6 |
C9—C8—C10 | 112.5 (2) | C22—C21—H21A | 107.6 |
N2—C8—H8A | 107.7 | C23—C21—H21A | 107.6 |
C9—C8—H8A | 107.7 | C21—C22—H22A | 109.5 |
C10—C8—H8A | 107.7 | C21—C22—H22B | 109.5 |
C8—C9—H9A | 109.5 | H22A—C22—H22B | 109.5 |
C8—C9—H9B | 109.5 | C21—C22—H22C | 109.5 |
H9A—C9—H9B | 109.5 | H22A—C22—H22C | 109.5 |
C8—C9—H9C | 109.5 | H22B—C22—H22C | 109.5 |
H9A—C9—H9C | 109.5 | C21—C23—H23A | 109.5 |
H9B—C9—H9C | 109.5 | C21—C23—H23B | 109.5 |
C8—C10—H10A | 109.5 | H23A—C23—H23B | 109.5 |
C8—C10—H10B | 109.5 | C21—C23—H23C | 109.5 |
H10A—C10—H10B | 109.5 | H23A—C23—H23C | 109.5 |
C8—C10—H10C | 109.5 | H23B—C23—H23C | 109.5 |
H10A—C10—H10C | 109.5 | N6—C24—C25 | 112.2 (2) |
H10B—C10—H10C | 109.5 | N6—C24—C26 | 109.7 (2) |
N3—C11—C12 | 114.5 (4) | C25—C24—C26 | 112.5 (2) |
N3—C11—C13 | 110.7 (4) | N6—C24—H24A | 107.4 |
C12—C11—C13 | 134.7 (5) | C25—C24—H24A | 107.4 |
N3—C11—C12' | 109.7 (3) | C26—C24—H24A | 107.4 |
C12—C11—C12' | 31.6 (4) | C24—C25—H25A | 109.5 |
C13—C11—C12' | 129.0 (4) | C24—C25—H25B | 109.5 |
N3—C11—C13' | 106.5 (3) | H25A—C25—H25B | 109.5 |
C12—C11—C13' | 115.8 (5) | C24—C25—H25C | 109.5 |
C13—C11—C13' | 49.7 (4) | H25A—C25—H25C | 109.5 |
C12'—C11—C13' | 89.6 (4) | H25B—C25—H25C | 109.5 |
N3—C11—H11A | 90.6 | C24—C26—H26A | 109.5 |
C12—C11—H11A | 90.6 | C24—C26—H26B | 109.5 |
C13—C11—H11A | 90.6 | H26A—C26—H26B | 109.5 |
C12'—C11—H11A | 59.1 | C24—C26—H26C | 109.5 |
C13'—C11—H11A | 41.1 | H26A—C26—H26C | 109.5 |
N3—C11—H11B | 116.0 | H26B—C26—H26C | 109.5 |
C12—C11—H11B | 87.7 | ||
O2—P1—N1—C7 | −171.46 (18) | C5—C6—C7—O1 | −163.0 (2) |
N2—P1—N1—C7 | 65.1 (2) | C1—C6—C7—O1 | 17.6 (3) |
N3—P1—N1—C7 | −48.8 (2) | C5—C6—C7—N1 | 18.1 (3) |
O2—P1—N2—C8 | −57.3 (2) | C1—C6—C7—N1 | −161.2 (2) |
N3—P1—N2—C8 | 176.46 (17) | P1—N2—C8—C9 | −109.6 (2) |
N1—P1—N2—C8 | 59.74 (19) | P1—N2—C8—C10 | 125.23 (19) |
O2—P1—N3—C11 | 43.7 (2) | P1—N3—C11—C12 | 75.4 (5) |
N2—P1—N3—C11 | 170.64 (18) | P1—N3—C11—C13 | −102.8 (4) |
N1—P1—N3—C11 | −73.4 (2) | P1—N3—C11—C12' | 109.2 (4) |
O4—P2—N4—C20 | 177.25 (18) | P1—N3—C11—C13' | −155.2 (3) |
N5—P2—N4—C20 | 56.0 (2) | C19—C14—C15—C16 | 1.7 (3) |
N6—P2—N4—C20 | −60.7 (2) | C14—C15—C16—F2 | 179.0 (2) |
O4—P2—N5—C21 | −41.3 (2) | C14—C15—C16—C17 | −0.6 (4) |
N6—P2—N5—C21 | −168.44 (19) | F2—C16—C17—C18 | 179.6 (2) |
N4—P2—N5—C21 | 77.2 (2) | C15—C16—C17—C18 | −0.8 (4) |
O4—P2—N6—C24 | −56.2 (2) | C16—C17—C18—C19 | 1.1 (4) |
N5—P2—N6—C24 | 68.8 (2) | C17—C18—C19—C14 | 0.0 (3) |
N4—P2—N6—C24 | −172.75 (17) | C17—C18—C19—C20 | 178.3 (2) |
C6—C1—C2—C3 | 0.4 (3) | C15—C14—C19—C18 | −1.4 (3) |
C1—C2—C3—F1 | −178.9 (2) | C15—C14—C19—C20 | −179.8 (2) |
C1—C2—C3—C4 | 1.2 (4) | P2—N4—C20—O3 | 9.1 (3) |
F1—C3—C4—C5 | 178.3 (2) | P2—N4—C20—C19 | −170.58 (16) |
C2—C3—C4—C5 | −1.8 (4) | C18—C19—C20—O3 | −161.9 (2) |
C3—C4—C5—C6 | 0.8 (4) | C14—C19—C20—O3 | 16.4 (3) |
C4—C5—C6—C1 | 0.8 (3) | C18—C19—C20—N4 | 17.7 (3) |
C4—C5—C6—C7 | −178.6 (2) | C14—C19—C20—N4 | −164.0 (2) |
C2—C1—C6—C5 | −1.4 (3) | P2—N5—C21—C22 | −92.0 (3) |
C2—C1—C6—C7 | 178.0 (2) | P2—N5—C21—C23 | 142.6 (3) |
P1—N1—C7—O1 | −2.4 (3) | P2—N6—C24—C25 | −94.2 (2) |
P1—N1—C7—C6 | 176.42 (15) | P2—N6—C24—C26 | 140.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4i | 0.87 (2) | 1.97 (2) | 2.832 (2) | 172 (2) |
N2—H2N···O3ii | 0.85 (2) | 2.18 (2) | 3.010 (2) | 167 (2) |
N3—H3N···O1 | 0.83 (2) | 2.51 (3) | 2.990 (3) | 118 (2) |
N4—H4N···O2iii | 0.85 (2) | 1.96 (2) | 2.802 (2) | 171 (3) |
N5—H5N···O1ii | 0.85 (2) | 2.15 (2) | 2.990 (2) | 167 (2) |
N6—H6N···O3 | 0.83 (2) | 2.51 (3) | 3.055 (3) | 124 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H21FN3O2P |
Mr | 301.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 15.9974 (12), 10.7474 (7), 19.5478 (13) |
β (°) | 111.461 (2) |
V (Å3) | 3127.8 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.22 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.959, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24038, 6366, 4979 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.627 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.140, 1.08 |
No. of reflections | 6366 |
No. of parameters | 385 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.28, −1.25 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4i | 0.868 (16) | 1.970 (17) | 2.832 (2) | 172 (2) |
N2—H2N···O3ii | 0.848 (16) | 2.177 (17) | 3.010 (2) | 167 (2) |
N3—H3N···O1 | 0.828 (17) | 2.51 (3) | 2.990 (3) | 118 (2) |
N4—H4N···O2iii | 0.849 (17) | 1.960 (17) | 2.802 (2) | 171 (3) |
N5—H5N···O1ii | 0.852 (17) | 2.154 (18) | 2.990 (2) | 167 (2) |
N6—H6N···O3 | 0.833 (17) | 2.51 (3) | 3.055 (3) | 124 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y+1/2, −z+3/2. |
Acknowledgements
Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.
References
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265–o272. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Raissi Shabari, A., Pourayoubi, M., Fadaei, H., Nečas, M. & Babiak, M. (2012). Acta Cryst. E68, o1813. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tarahhomi, A., Pourayoubi, M., Rheingold, A. L. & Golen, J. A. (2011). Struct. Chem. 22, 201–210. Web of Science CSD CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The structure determination of the title compound, [4-F—C6H4C(O)NH]P(O)[NHCH(CH3)2]2 (Fig. 1), was performed as a part of a project on the synthesis of new phosphoric triamides with a [C(O)NH]P(O)[NHC]2 skeleton (Pourayoubi et al., 2011; Raissi Shabari et al., 2012).
The asymmetric unit of the title compound consists of two independent molecules. In one molecule, disorder with respect to the methyl carbon atoms C12 and C13 of an isopropyl group was treated using a two-part model (45.8/54.2) with restrained C—C distances of 1.55 (0.02) Å.
In the C(O)NHP(O) fragment, the phosphoryl group adopts a syn orientation with respect to the N—H unit. The P atoms are in a distorted tetrahedral environment as has been noted for other phosphoric triamides (Pourayoubi et al., 2011). The P═O, C═O and P—N bond lengths and the P—N—C bond angles are within the expected values (Pourayoubi et al., 2011; Raissi Shabari et al., 2012).
In the crystal structure, the molecules are linked through N—H···O(═P) and N—H···O(═C) hydrogen bonds into chains along [001], giving R22(8) and R22(12) rings (Fig. 2). This sequence of ring motifs is similar to most of the phosphoric triamides with a [C(O)NH]P(O)[NHC]2 skeleton (Pourayoubi et al., 2011). Moreover, two intramolecular N—H···O(═C) hydrogen bonds (Table 1) are found in the structure.