supplementary materials


ff2089 scheme

Acta Cryst. (2012). E68, o3406-o3407    [ doi:10.1107/S1600536812046326 ]

N-(4-Fluorobenzoyl)-N',N''-diisopropylphosphoric triamide

M. Pourayoubi, A. Tarahhomi, A. L. Rheingold and J. A. Golen

Abstract top

The asymmetric unit of the title phosphoric triamide, C13H21FN3O2P, 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].

Comment top

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 PO, CO 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.

Related literature top

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 top

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.

Refinement top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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.
N-(4-Fluorobenzoyl)-N',N''-diisopropylphosphoric triamide top
Crystal data top
C13H21FN3O2PF(000) = 1280
Mr = 301.30Dx = 1.280 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.9974 (12) ÅCell parameters from 6765 reflections
b = 10.7474 (7) Åθ = 2.7–26.4°
c = 19.5478 (13) ŵ = 0.19 mm1
β = 111.461 (2)°T = 100 K
V = 3127.8 (4) Å3Block, colourless
Z = 80.22 × 0.20 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
6366 independent reflections
Radiation source: fine-focus sealed tube4979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2019
Tmin = 0.959, Tmax = 0.972k = 1213
24038 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H 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 parametersΔρmax = 1.28 e Å3
11 restraintsΔρmin = 1.25 e Å3
Crystal data top
C13H21FN3O2PV = 3127.8 (4) Å3
Mr = 301.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.9974 (12) ŵ = 0.19 mm1
b = 10.7474 (7) ÅT = 100 K
c = 19.5478 (13) Å0.22 × 0.20 × 0.15 mm
β = 111.461 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
6366 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
4979 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.972Rint = 0.035
24038 measured reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140Δρmax = 1.28 e Å3
S = 1.08Δρmin = 1.25 e Å3
6366 reflectionsAbsolute structure: ?
385 parametersFlack parameter: ?
11 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.66641 (4)0.16703 (5)0.60938 (3)0.01446 (15)
P20.21362 (4)0.66868 (5)0.64779 (3)0.01601 (15)
F11.19973 (10)0.26579 (16)0.81566 (8)0.0353 (4)
F20.75090 (10)0.72695 (16)0.81958 (8)0.0346 (4)
O10.81182 (11)0.27790 (16)0.57067 (9)0.0233 (4)
O20.62755 (10)0.11428 (15)0.66103 (8)0.0184 (3)
O30.34880 (12)0.81368 (16)0.60767 (9)0.0257 (4)
O40.18241 (11)0.59057 (15)0.69603 (8)0.0191 (3)
N10.77938 (13)0.17148 (18)0.65776 (10)0.0167 (4)
H1N0.7967 (17)0.148 (2)0.7034 (10)0.020*
N20.64876 (13)0.08672 (17)0.53551 (10)0.0163 (4)
H2N0.6444 (17)0.124 (2)0.4962 (11)0.020*
N30.63066 (14)0.30688 (18)0.58047 (11)0.0199 (4)
H3N0.6526 (18)0.333 (2)0.5509 (13)0.024*
N40.32492 (13)0.69042 (18)0.69250 (10)0.0182 (4)
H4N0.3451 (17)0.668 (2)0.7372 (10)0.022*
N50.19346 (14)0.60247 (18)0.56892 (10)0.0190 (4)
H5N0.1955 (18)0.647 (2)0.5336 (12)0.023*
N60.17165 (14)0.80866 (19)0.63345 (11)0.0225 (4)
H6N0.2011 (18)0.861 (2)0.6202 (15)0.027*
C10.98985 (16)0.3212 (2)0.66618 (13)0.0214 (5)
H1B0.96550.37380.62450.026*
C21.07965 (17)0.3330 (2)0.71090 (14)0.0239 (5)
H2C1.11720.39310.70090.029*
C31.11214 (16)0.2545 (2)0.77028 (13)0.0240 (5)
C41.06095 (17)0.1645 (2)0.78636 (13)0.0248 (5)
H4C1.08650.11050.82720.030*
C50.97113 (16)0.1547 (2)0.74148 (12)0.0204 (5)
H5B0.93430.09400.75190.024*
C60.93470 (15)0.2335 (2)0.68126 (12)0.0163 (4)
C70.83791 (15)0.2292 (2)0.63192 (12)0.0174 (5)
C80.67839 (16)0.0441 (2)0.54144 (13)0.0216 (5)
H8A0.69910.06830.59440.026*
C90.75718 (18)0.0592 (3)0.51657 (15)0.0314 (6)
H9A0.80620.00410.54550.047*
H9B0.73840.03770.46440.047*
H9C0.77790.14580.52380.047*
C100.59970 (19)0.1273 (3)0.49919 (16)0.0339 (6)
H10A0.55110.11530.51780.051*
H10B0.61900.21450.50570.051*
H10C0.57820.10590.44690.051*
C110.62386 (19)0.4006 (2)0.63394 (14)0.0293 (6)
H11A0.61680.46870.59740.044*0.458 (5)
H11B0.61670.36690.67920.044*0.542 (5)
C120.7119 (6)0.4539 (9)0.6829 (5)0.0619 (11)0.458 (5)
H12A0.73760.40140.72660.093*0.458 (5)
H12B0.70260.53820.69780.093*0.458 (5)
H12C0.75320.45700.65620.093*0.458 (5)
C130.5276 (6)0.4168 (8)0.6273 (5)0.0619 (11)0.458 (5)
H13A0.49950.33490.62440.093*0.458 (5)
H13B0.49480.46440.58280.093*0.458 (5)
H13C0.52580.46150.67040.093*0.458 (5)
C12'0.6977 (5)0.5009 (7)0.6466 (5)0.0619 (11)0.542 (5)
H12D0.75650.46500.67520.093*0.542 (5)
H12E0.68570.57120.67360.093*0.542 (5)
H12F0.69770.52990.59910.093*0.542 (5)
C13'0.5514 (5)0.4973 (6)0.5888 (4)0.0619 (11)0.542 (5)
H13D0.49170.45900.57310.093*0.542 (5)
H13E0.56390.52350.54550.093*0.542 (5)
H13F0.55320.57000.61960.093*0.542 (5)
C140.53551 (17)0.8319 (2)0.69340 (13)0.0209 (5)
H14A0.51090.89410.65700.025*
C150.62753 (17)0.8276 (2)0.73154 (14)0.0245 (5)
H15A0.66640.88720.72290.029*
C160.66076 (16)0.7340 (2)0.78238 (13)0.0241 (5)
C170.60747 (17)0.6462 (2)0.79746 (13)0.0248 (5)
H17A0.63300.58230.83250.030*
C180.51529 (16)0.6533 (2)0.75999 (13)0.0227 (5)
H18A0.47700.59460.77010.027*
C190.47844 (16)0.7459 (2)0.70771 (12)0.0179 (5)
C200.37995 (16)0.7536 (2)0.66527 (12)0.0186 (5)
C210.20729 (17)0.4683 (2)0.56179 (13)0.0232 (5)
H21A0.20130.42570.60530.028*
C220.2994 (2)0.4408 (3)0.5623 (2)0.0550 (9)
H22A0.34440.48110.60490.082*
H22B0.30460.47280.51710.082*
H22C0.30930.35070.56520.082*
C230.1340 (3)0.4201 (3)0.4942 (2)0.0723 (14)
H23A0.07540.43780.49740.108*
H23B0.14090.33000.49040.108*
H23C0.13780.46100.45060.108*
C240.07352 (18)0.8274 (2)0.60296 (14)0.0277 (6)
H24A0.04530.75120.61450.033*
C250.0378 (2)0.8417 (3)0.52048 (15)0.0354 (7)
H25A0.05210.76700.49820.053*
H25B0.06550.91450.50720.053*
H25C0.02750.85290.50250.053*
C260.0489 (2)0.9359 (3)0.64109 (16)0.0430 (8)
H26A0.06940.91930.69400.064*
H26B0.01650.94700.62140.064*
H26C0.07771.01170.63260.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0147 (3)0.0187 (3)0.0103 (3)0.0003 (2)0.0049 (2)0.0013 (2)
P20.0177 (3)0.0191 (3)0.0117 (3)0.0005 (2)0.0059 (2)0.0002 (2)
F10.0164 (8)0.0524 (10)0.0328 (8)0.0072 (7)0.0038 (6)0.0086 (7)
F20.0178 (8)0.0483 (10)0.0357 (9)0.0050 (7)0.0076 (6)0.0064 (7)
O10.0236 (9)0.0325 (9)0.0150 (8)0.0006 (7)0.0085 (7)0.0053 (7)
O20.0179 (8)0.0257 (8)0.0128 (7)0.0031 (7)0.0070 (6)0.0031 (6)
O30.0286 (10)0.0303 (9)0.0171 (8)0.0017 (7)0.0072 (7)0.0081 (7)
O40.0197 (9)0.0259 (9)0.0128 (7)0.0032 (7)0.0070 (6)0.0004 (6)
N10.0157 (10)0.0243 (10)0.0096 (8)0.0030 (8)0.0039 (7)0.0006 (7)
N20.0196 (10)0.0201 (10)0.0086 (8)0.0011 (8)0.0044 (7)0.0010 (7)
N30.0234 (11)0.0206 (10)0.0172 (10)0.0028 (8)0.0093 (8)0.0005 (8)
N40.0191 (10)0.0253 (10)0.0097 (9)0.0015 (8)0.0047 (7)0.0034 (7)
N50.0265 (11)0.0193 (10)0.0123 (9)0.0025 (8)0.0084 (8)0.0021 (7)
N60.0251 (12)0.0198 (10)0.0228 (10)0.0026 (8)0.0091 (9)0.0005 (8)
C10.0225 (13)0.0202 (12)0.0264 (12)0.0010 (9)0.0146 (10)0.0008 (9)
C20.0213 (13)0.0214 (12)0.0341 (14)0.0048 (10)0.0163 (11)0.0051 (10)
C30.0148 (12)0.0341 (14)0.0235 (12)0.0031 (10)0.0076 (9)0.0100 (10)
C40.0206 (13)0.0354 (14)0.0178 (11)0.0021 (11)0.0063 (10)0.0037 (10)
C50.0179 (12)0.0259 (12)0.0187 (11)0.0023 (9)0.0082 (9)0.0013 (9)
C60.0159 (11)0.0201 (11)0.0147 (10)0.0008 (9)0.0079 (9)0.0025 (8)
C70.0201 (12)0.0192 (11)0.0152 (11)0.0008 (9)0.0089 (9)0.0007 (9)
C80.0252 (13)0.0219 (12)0.0169 (11)0.0032 (10)0.0067 (9)0.0015 (9)
C90.0239 (14)0.0318 (14)0.0384 (15)0.0035 (11)0.0112 (12)0.0096 (12)
C100.0354 (16)0.0271 (14)0.0448 (17)0.0065 (12)0.0215 (13)0.0123 (12)
C110.0413 (16)0.0229 (13)0.0277 (13)0.0037 (11)0.0173 (12)0.0055 (10)
C120.083 (3)0.046 (2)0.070 (3)0.003 (2)0.044 (2)0.0214 (19)
C130.083 (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)
C140.0285 (13)0.0173 (11)0.0218 (12)0.0018 (10)0.0151 (10)0.0013 (9)
C150.0243 (13)0.0227 (12)0.0329 (13)0.0075 (10)0.0179 (11)0.0054 (10)
C160.0173 (12)0.0326 (13)0.0232 (12)0.0034 (10)0.0082 (10)0.0093 (10)
C170.0234 (13)0.0334 (14)0.0185 (11)0.0007 (10)0.0088 (10)0.0034 (10)
C180.0214 (13)0.0295 (13)0.0183 (11)0.0033 (10)0.0085 (10)0.0041 (10)
C190.0225 (12)0.0200 (11)0.0139 (10)0.0019 (9)0.0099 (9)0.0023 (8)
C200.0242 (13)0.0186 (11)0.0140 (10)0.0005 (9)0.0081 (9)0.0002 (9)
C210.0321 (14)0.0202 (12)0.0188 (11)0.0048 (10)0.0111 (10)0.0010 (9)
C220.053 (2)0.0428 (19)0.080 (3)0.0130 (16)0.037 (2)0.0067 (18)
C230.061 (2)0.0353 (18)0.087 (3)0.0087 (17)0.013 (2)0.0311 (19)
C240.0289 (14)0.0278 (13)0.0281 (13)0.0090 (11)0.0124 (11)0.0041 (10)
C250.0352 (16)0.0377 (15)0.0277 (14)0.0128 (12)0.0048 (12)0.0006 (12)
C260.053 (2)0.0476 (18)0.0314 (15)0.0243 (15)0.0183 (14)0.0018 (13)
Geometric parameters (Å, º) top
P1—O21.4788 (16)C11—C12'1.551 (7)
P1—N21.6159 (18)C11—C13'1.567 (7)
P1—N31.634 (2)C11—H11A1.0000
P1—N11.7065 (19)C11—H11B1.0000
P2—O41.4792 (16)C12—H12A0.9800
P2—N51.6197 (19)C12—H12B0.9800
P2—N61.629 (2)C12—H12C0.9800
P2—N41.688 (2)C13—H13A0.9800
F1—C31.362 (3)C13—H13B0.9800
F2—C161.359 (3)C13—H13C0.9800
O1—C71.231 (3)C12'—H12D0.9800
O3—C201.234 (3)C12'—H12E0.9800
N1—C71.365 (3)C12'—H12F0.9800
N1—H1N0.868 (16)C13'—H13D0.9800
N2—C81.475 (3)C13'—H13E0.9800
N2—H2N0.848 (16)C13'—H13F0.9800
N3—C111.484 (3)C14—C151.386 (4)
N3—H3N0.828 (17)C14—C191.397 (3)
N4—C201.364 (3)C14—H14A0.9500
N4—H4N0.849 (17)C15—C161.377 (4)
N5—C211.473 (3)C15—H15A0.9500
N5—H5N0.852 (17)C16—C171.374 (4)
N6—C241.475 (3)C17—C181.388 (3)
N6—H6N0.833 (17)C17—H17A0.9500
C1—C21.388 (3)C18—C191.393 (3)
C1—C61.395 (3)C18—H18A0.9500
C1—H1B0.9500C19—C201.490 (3)
C2—C31.374 (4)C21—C221.498 (4)
C2—H2C0.9500C21—C231.502 (4)
C3—C41.375 (4)C21—H21A1.0000
C4—C51.387 (3)C22—H22A0.9800
C4—H4C0.9500C22—H22B0.9800
C5—C61.393 (3)C22—H22C0.9800
C5—H5B0.9500C23—H23A0.9800
C6—C71.496 (3)C23—H23B0.9800
C8—C91.516 (4)C23—H23C0.9800
C8—C101.519 (4)C24—C251.509 (4)
C8—H8A1.0000C24—C261.512 (4)
C9—H9A0.9800C24—H24A1.0000
C9—H9B0.9800C25—H25A0.9800
C9—H9C0.9800C25—H25B0.9800
C10—H10A0.9800C25—H25C0.9800
C10—H10B0.9800C26—H26A0.9800
C10—H10C0.9800C26—H26B0.9800
C11—C121.497 (9)C26—H26C0.9800
C11—C131.508 (8)
O2—P1—N2115.19 (10)C13—C11—H11B71.0
O2—P1—N3114.04 (10)C12'—C11—H11B116.0
N2—P1—N3104.94 (10)C13'—C11—H11B116.0
O2—P1—N1104.88 (9)H11A—C11—H11B151.4
N2—P1—N1108.28 (10)C11—C12—H12A109.5
N3—P1—N1109.37 (10)C11—C12—H12B109.5
O4—P2—N5111.19 (10)H12A—C12—H12B109.5
O4—P2—N6114.82 (10)C11—C12—H12C109.5
N5—P2—N6108.42 (10)H12A—C12—H12C109.5
O4—P2—N4106.65 (9)H12B—C12—H12C109.5
N5—P2—N4111.01 (10)C11—C13—H13A109.5
N6—P2—N4104.57 (11)C11—C13—H13B109.5
C7—N1—P1122.57 (16)H13A—C13—H13B109.5
C7—N1—H1N120.4 (17)C11—C13—H13C109.5
P1—N1—H1N115.9 (17)H13A—C13—H13C109.5
C8—N2—P1119.54 (15)H13B—C13—H13C109.5
C8—N2—H2N116.2 (18)C11—C12'—H12D109.5
P1—N2—H2N119.1 (18)C11—C12'—H12E109.5
C11—N3—P1119.18 (16)H12D—C12'—H12E109.5
C11—N3—H3N114.6 (19)C11—C12'—H12F109.5
P1—N3—H3N112.0 (19)H12D—C12'—H12F109.5
C20—N4—P2125.15 (16)H12E—C12'—H12F109.5
C20—N4—H4N119.2 (18)C11—C13'—H13D109.5
P2—N4—H4N115.2 (18)C11—C13'—H13E109.5
C21—N5—P2122.39 (16)H13D—C13'—H13E109.5
C21—N5—H5N115.1 (18)C11—C13'—H13F109.5
P2—N5—H5N118.0 (18)H13D—C13'—H13F109.5
C24—N6—P2120.41 (17)H13E—C13'—H13F109.5
C24—N6—H6N115 (2)C15—C14—C19120.9 (2)
P2—N6—H6N116 (2)C15—C14—H14A119.6
C2—C1—C6121.2 (2)C19—C14—H14A119.6
C2—C1—H1B119.4C16—C15—C14117.8 (2)
C6—C1—H1B119.4C16—C15—H15A121.1
C3—C2—C1117.4 (2)C14—C15—H15A121.1
C3—C2—H2C121.3F2—C16—C17117.8 (2)
C1—C2—H2C121.3F2—C16—C15118.7 (2)
F1—C3—C2118.4 (2)C17—C16—C15123.4 (2)
F1—C3—C4118.1 (2)C16—C17—C18118.1 (2)
C2—C3—C4123.5 (2)C16—C17—H17A120.9
C3—C4—C5118.3 (2)C18—C17—H17A120.9
C3—C4—H4C120.8C17—C18—C19120.6 (2)
C5—C4—H4C120.8C17—C18—H18A119.7
C4—C5—C6120.3 (2)C19—C18—H18A119.7
C4—C5—H5B119.8C18—C19—C14119.1 (2)
C6—C5—H5B119.8C18—C19—C20121.7 (2)
C5—C6—C1119.2 (2)C14—C19—C20119.2 (2)
C5—C6—C7122.7 (2)O3—C20—N4120.9 (2)
C1—C6—C7118.0 (2)O3—C20—C19121.9 (2)
O1—C7—N1121.2 (2)N4—C20—C19117.19 (19)
O1—C7—C6121.1 (2)N5—C21—C22111.9 (2)
N1—C7—C6117.63 (19)N5—C21—C23109.0 (2)
N2—C8—C9111.0 (2)C22—C21—C23112.8 (3)
N2—C8—C10109.9 (2)N5—C21—H21A107.6
C9—C8—C10112.5 (2)C22—C21—H21A107.6
N2—C8—H8A107.7C23—C21—H21A107.6
C9—C8—H8A107.7C21—C22—H22A109.5
C10—C8—H8A107.7C21—C22—H22B109.5
C8—C9—H9A109.5H22A—C22—H22B109.5
C8—C9—H9B109.5C21—C22—H22C109.5
H9A—C9—H9B109.5H22A—C22—H22C109.5
C8—C9—H9C109.5H22B—C22—H22C109.5
H9A—C9—H9C109.5C21—C23—H23A109.5
H9B—C9—H9C109.5C21—C23—H23B109.5
C8—C10—H10A109.5H23A—C23—H23B109.5
C8—C10—H10B109.5C21—C23—H23C109.5
H10A—C10—H10B109.5H23A—C23—H23C109.5
C8—C10—H10C109.5H23B—C23—H23C109.5
H10A—C10—H10C109.5N6—C24—C25112.2 (2)
H10B—C10—H10C109.5N6—C24—C26109.7 (2)
N3—C11—C12114.5 (4)C25—C24—C26112.5 (2)
N3—C11—C13110.7 (4)N6—C24—H24A107.4
C12—C11—C13134.7 (5)C25—C24—H24A107.4
N3—C11—C12'109.7 (3)C26—C24—H24A107.4
C12—C11—C12'31.6 (4)C24—C25—H25A109.5
C13—C11—C12'129.0 (4)C24—C25—H25B109.5
N3—C11—C13'106.5 (3)H25A—C25—H25B109.5
C12—C11—C13'115.8 (5)C24—C25—H25C109.5
C13—C11—C13'49.7 (4)H25A—C25—H25C109.5
C12'—C11—C13'89.6 (4)H25B—C25—H25C109.5
N3—C11—H11A90.6C24—C26—H26A109.5
C12—C11—H11A90.6C24—C26—H26B109.5
C13—C11—H11A90.6H26A—C26—H26B109.5
C12'—C11—H11A59.1C24—C26—H26C109.5
C13'—C11—H11A41.1H26A—C26—H26C109.5
N3—C11—H11B116.0H26B—C26—H26C109.5
C12—C11—H11B87.7
O2—P1—N1—C7171.46 (18)C5—C6—C7—O1163.0 (2)
N2—P1—N1—C765.1 (2)C1—C6—C7—O117.6 (3)
N3—P1—N1—C748.8 (2)C5—C6—C7—N118.1 (3)
O2—P1—N2—C857.3 (2)C1—C6—C7—N1161.2 (2)
N3—P1—N2—C8176.46 (17)P1—N2—C8—C9109.6 (2)
N1—P1—N2—C859.74 (19)P1—N2—C8—C10125.23 (19)
O2—P1—N3—C1143.7 (2)P1—N3—C11—C1275.4 (5)
N2—P1—N3—C11170.64 (18)P1—N3—C11—C13102.8 (4)
N1—P1—N3—C1173.4 (2)P1—N3—C11—C12'109.2 (4)
O4—P2—N4—C20177.25 (18)P1—N3—C11—C13'155.2 (3)
N5—P2—N4—C2056.0 (2)C19—C14—C15—C161.7 (3)
N6—P2—N4—C2060.7 (2)C14—C15—C16—F2179.0 (2)
O4—P2—N5—C2141.3 (2)C14—C15—C16—C170.6 (4)
N6—P2—N5—C21168.44 (19)F2—C16—C17—C18179.6 (2)
N4—P2—N5—C2177.2 (2)C15—C16—C17—C180.8 (4)
O4—P2—N6—C2456.2 (2)C16—C17—C18—C191.1 (4)
N5—P2—N6—C2468.8 (2)C17—C18—C19—C140.0 (3)
N4—P2—N6—C24172.75 (17)C17—C18—C19—C20178.3 (2)
C6—C1—C2—C30.4 (3)C15—C14—C19—C181.4 (3)
C1—C2—C3—F1178.9 (2)C15—C14—C19—C20179.8 (2)
C1—C2—C3—C41.2 (4)P2—N4—C20—O39.1 (3)
F1—C3—C4—C5178.3 (2)P2—N4—C20—C19170.58 (16)
C2—C3—C4—C51.8 (4)C18—C19—C20—O3161.9 (2)
C3—C4—C5—C60.8 (4)C14—C19—C20—O316.4 (3)
C4—C5—C6—C10.8 (3)C18—C19—C20—N417.7 (3)
C4—C5—C6—C7178.6 (2)C14—C19—C20—N4164.0 (2)
C2—C1—C6—C51.4 (3)P2—N5—C21—C2292.0 (3)
C2—C1—C6—C7178.0 (2)P2—N5—C21—C23142.6 (3)
P1—N1—C7—O12.4 (3)P2—N6—C24—C2594.2 (2)
P1—N1—C7—C6176.42 (15)P2—N6—C24—C26140.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.87 (2)1.97 (2)2.832 (2)172 (2)
N2—H2N···O3ii0.85 (2)2.18 (2)3.010 (2)167 (2)
N3—H3N···O10.83 (2)2.51 (3)2.990 (3)118 (2)
N4—H4N···O2iii0.85 (2)1.96 (2)2.802 (2)171 (3)
N5—H5N···O1ii0.85 (2)2.15 (2)2.990 (2)167 (2)
N6—H6N···O30.83 (2)2.51 (3)3.055 (3)124 (2)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1, z+1; (iii) x+1, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O4i0.868 (16)1.970 (17)2.832 (2)172 (2)
N2—H2N···O3ii0.848 (16)2.177 (17)3.010 (2)167 (2)
N3—H3N···O10.828 (17)2.51 (3)2.990 (3)118 (2)
N4—H4N···O2iii0.849 (17)1.960 (17)2.802 (2)171 (3)
N5—H5N···O1ii0.852 (17)2.154 (18)2.990 (2)167 (2)
N6—H6N···O30.833 (17)2.51 (3)3.055 (3)124 (2)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+1, y+1, z+1; (iii) x+1, y+1/2, z+3/2.
Acknowledgements top

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

references
References top

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