N,N′-Dicyclo­hexyl-N′′-(3-fluoro­benzo­yl)-N,N′-dimethyl­phospho­ric triamide

Pourayoubi, M.; Shoghpour, S.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811043017

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Pages o3028-o3029

doi:10.1107/S1600536811043017

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N,N′-Dicyclohexyl-N′′-(3-fluorobenzoyl)-N,N′-dimethylphosphoric triamide

Mehrdad Pourayoubi,^a ^* Samad Shoghpour,^a Giuseppe Bruno ^b and Hadi Amiri Rudbari ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Università di Messina, 98166 Messina, Italy
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 30 September 2011; accepted 17 October 2011; online 22 October 2011)

In the title compound, C₂₁H₃₃FN₃O₂P, the P atom has a distorted tetrahedral environment and the N atoms display geometries consistent with a model of sp² hybridization (with bond-angle sums for the tertiary N atoms of 357.8 and 358.7°). The phosphoryl and carbonyl groups are anti with respect to each other. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For the coordination properties of carbacylamidophosphates, see: Pourayoubi et al. (2011b ); Gholivand et al. (2010 ); Znovjyak et al. (2009 ); Trush et al. (2005 ); Gubina et al. (2002 ). For related structures, see: Pourayoubi et al. (2011a ); Pourayoubi & Saneei (2011 ). For the syn orientation of the P(=O) group and NH unit in the C(O)NHP(O) skeleton for most known carbacylamidophosphates, see: Toghraee et al. (2011 ). For a procedure to synthesise the starting phosphorus–chlorine compound, see: Pourayoubi et al. (2011c ). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₁H₃₃FN₃O₂P
M_r = 409.47
Monoclinic, C 2/c
a = 22.6634 (8) Å
b = 12.9587 (5) Å
c = 17.6627 (7) Å
β = 119.061 (1)°
V = 4534.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 296 K
0.32 × 0.28 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.658, T_max = 0.746
20958 measured reflections
4228 independent reflections
3254 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.157
S = 1.02
4228 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.93 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.78 (2)	2.04 (2)	2.807 (2)	165 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043017/qm2034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043017/qm2034Isup2.hkl

checkCIF report

Comment top

It is now well recognized that carbacylamidophosphates offer very good candidates for coordination chemistry purposes, since they bear a C(O)NHP(O) bifunctional group which is the phosphaza- analogue of β-diketones. In this context, a variety of coordination compounds with both transition and non-transition metal cations have been reported (Pourayoubi et al., 2011b; Gholivand et al., 2010; Znovjyak et al., 2009; Trush et al., 2005; Gubina et al., 2002). Therefore, the synthesis and crystal structure investigations of carbacylamidophosphates have been of particular interest in our research team (Pourayoubi et al., 2011a; Pourayoubi & Saneei, 2011). In this work, the synthesis and crystal structure of a new carbacylamidophosphate, P(O)[NHC(O)C₆H₄(3-F)][N(CH₃)(C₆H₁₁)]₂, is reported. The molecular structure (ORTEP view) of the title compound is shown in Fig. 1. The phosphoryl group and the NH unit are located in a syn position with respect to each other similar to most of the carbacylamidophosphates (Toghraee et al., 2011). The P atom has a distorted tetrahedral configuration with the bond angles around the P atom in the range of 105.9 (1)–116.4 (1)°. The P═O, C═O and P—N bond lengths and the P—N—C bond angles are in the range of the expected values. The sum of the surrounding angles around the tertiary N atoms confirms their sp² hybridization. In the crystal structure, two neighboring molecules are hydrogen-bonded to each other by two equal intermolecular P═O···H—N hydrogen bonds (O1···N1 = 2.807 (2) Å) (Table 1) to form a centrosymmetric dimer as an R₂²(8) ring.

Related literature top

For the coordination properties of carbacylamidophosphates, see: Pourayoubi et al. (2011b); Gholivand et al. (2010); Znovjyak et al. (2009); Trush et al. (2005); Gubina et al. (2002). For related structures, see: Pourayoubi et al. (2011a); Pourayoubi & Saneei (2011). For the syn orientation of the P(═O) group and NH unit in the C(O)NHP(O) skeleton for most known carbacylamidophosphates, see: Toghraee et al. (2011). For a procedure to synthesise the starting phosphorus–chlorine compound, see: Pourayoubi et al. (2011c). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

Synthesis of 3-F–C₆H₄C(O)NHP(O)Cl₂ 3-F–C₆H₄C(O)NHP(O)Cl₂ was prepared according to the procedure which was previously used for preparation of 2-F–C₆H₄C(O)NHP(O)Cl₂ (Pourayoubi et al., 2011c) by using 3-F–C₆H₄C(O)NH₂ instead of 2-F–C₆H₄C(O)NH₂. Synthesis of the title molecule To a solution of 3-F–C₆H₄C(O)NHP(O)Cl₂ (0.512 g, 2 mmol) in CHCl₃ (20 ml), a solution of N-methylcyclohexylamine (0.906 g, 8 mmol) in CHCl₃ (5 ml) was added dropwise at 273 K. After 4 h stirring, the solvent was evaporated in vacuo and then the resulting solid was washed with water. Single crystals of title compound were obtained from a solution of CH₃OH and CHCl₃ (2:1) after slow evaporation at room temperature. IR (KBr, cm^-1): 3068 (NH), 2930, 2855, 1685 (C═O), 1589, 1491, 1448, 1393, 1287, 1272, 1181, 1161, 1005, 982, 886, 860, 749, 682.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XPW (Siemens, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

Fig. 1. An ORTEP-style plot of title compound with labeling. Ellipsoids are given at the 50% probability level.

N,N'-Dicyclohexyl-N''-(3-fluorobenzoyl)- N,N'-dimethylphosphoric triamide top

Crystal data top

C₂₁H₃₃FN₃O₂P	F(000) = 1760
M_r = 409.47	D_x = 1.200 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8133 reflections
a = 22.6634 (8) Å	θ = 2.4–27.0°
b = 12.9587 (5) Å	µ = 0.15 mm⁻¹
c = 17.6627 (7) Å	T = 296 K
β = 119.061 (1)°	Cubic, colourless
V = 4534.3 (3) Å³	0.32 × 0.28 × 0.16 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	4228 independent reflections
Radiation source: fine-focus sealed tube	3254 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −27→27
T_min = 0.658, T_max = 0.746	k = −15→15
20958 measured reflections	l = −21→21

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0936P)² + 3.0653P] where P = (F_o² + 2F_c²)/3
4228 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.93 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₁H₃₃FN₃O₂P	V = 4534.3 (3) Å³
M_r = 409.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.6634 (8) Å	µ = 0.15 mm⁻¹
b = 12.9587 (5) Å	T = 296 K
c = 17.6627 (7) Å	0.32 × 0.28 × 0.16 mm
β = 119.061 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4228 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	3254 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.746	R_int = 0.031
20958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.93 e Å⁻³
4228 reflections	Δρ_min = −0.29 e Å⁻³
257 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	U_iso*/U_eq
P1	0.19691 (2)	0.87686 (4)	0.02588 (3)	0.03552 (19)
O2	0.30019 (9)	0.98806 (14)	0.18782 (12)	0.0637 (5)
F1	0.46037 (14)	0.6077 (2)	0.31270 (17)	0.1416 (10)
O1	0.16844 (7)	0.78142 (11)	−0.02507 (9)	0.0426 (4)
N1	0.27588 (8)	0.84697 (15)	0.10211 (11)	0.0370 (4)
C1	0.31644 (10)	0.90341 (18)	0.17448 (13)	0.0417 (5)
C3	0.15054 (14)	1.02308 (19)	0.0955 (2)	0.0618 (7)
H3A	0.1710	1.0669	0.0709	0.093*
H3B	0.1751	1.0282	0.1575	0.093*
H3C	0.1047	1.0443	0.0749	0.093*
N2	0.20318 (9)	0.97566 (15)	−0.02662 (12)	0.0479 (5)
C19	0.0611 (3)	0.7585 (4)	0.2030 (4)	0.135 (2)
H19A	0.0582	0.8200	0.2323	0.162*
H19B	0.0428	0.7012	0.2204	0.162*
C20	0.0200 (2)	0.7734 (4)	0.1057 (4)	0.1268 (18)
H20A	−0.0261	0.7903	0.0905	0.152*
H20B	0.0193	0.7094	0.0769	0.152*
C21	0.04874 (15)	0.8595 (3)	0.0735 (2)	0.0828 (10)
H21A	0.0231	0.8637	0.0108	0.099*
H21B	0.0450	0.9252	0.0971	0.099*
C16	0.12210 (11)	0.83718 (19)	0.10158 (15)	0.0477 (5)
H16	0.1235	0.7713	0.0752	0.057*
N3	0.15171 (9)	0.91587 (14)	0.06955 (12)	0.0429 (4)
C4	0.38187 (11)	0.8550 (2)	0.23687 (13)	0.0458 (6)
C5	0.39071 (12)	0.7492 (2)	0.24479 (15)	0.0563 (6)
H5	0.3560	0.7044	0.2099	0.068*
C6	0.45265 (15)	0.7122 (3)	0.30609 (18)	0.0740 (9)
C7	0.50556 (14)	0.7743 (4)	0.35762 (17)	0.0865 (12)
H7	0.5470	0.7466	0.3975	0.104*
C18	0.1330 (3)	0.7373 (3)	0.2291 (3)	0.1109 (15)
H18A	0.1362	0.6723	0.2041	0.133*
H18B	0.1588	0.7311	0.2917	0.133*
C17	0.16264 (17)	0.8231 (3)	0.19916 (18)	0.0774 (9)
H17A	0.1626	0.8871	0.2277	0.093*
H17B	0.2090	0.8064	0.2154	0.093*
C10	0.26677 (11)	1.00986 (18)	−0.02259 (15)	0.0462 (5)
H10	0.3035	0.9781	0.0293	0.055*
C15	0.27532 (14)	0.9741 (2)	−0.09852 (16)	0.0599 (7)
H15A	0.2726	0.8994	−0.1022	0.072*
H15B	0.2390	1.0019	−0.1518	0.072*
C14	0.34258 (17)	1.0089 (3)	−0.0885 (2)	0.0776 (9)
H14A	0.3454	0.9893	−0.1397	0.093*
H14B	0.3788	0.9743	−0.0391	0.093*
C13	0.35163 (19)	1.1247 (3)	−0.0759 (2)	0.0881 (10)
H13A	0.3961	1.1439	−0.0664	0.106*
H13B	0.3183	1.1595	−0.1277	0.106*
C12	0.34381 (19)	1.1582 (3)	0.0008 (3)	0.0898 (10)
H12A	0.3480	1.2326	0.0066	0.108*
H12B	0.3796	1.1278	0.0532	0.108*
C11	0.27582 (17)	1.1256 (2)	−0.0098 (2)	0.0723 (8)
H11A	0.2729	1.1454	0.0412	0.087*
H11B	0.2400	1.1606	−0.0594	0.087*
C2	0.13971 (13)	1.0138 (2)	−0.09931 (19)	0.0692 (8)
H2A	0.1022	0.9864	−0.0948	0.104*
H2B	0.1367	0.9921	−0.1530	0.104*
H2C	0.1389	1.0878	−0.0975	0.104*
C9	0.43442 (12)	0.9204 (3)	0.28957 (16)	0.0652 (7)
H9	0.4284	0.9915	0.2851	0.078*
C8	0.49597 (15)	0.8784 (4)	0.34893 (19)	0.0887 (12)
H8	0.5315	0.9221	0.3836	0.106*
H1	0.2925 (11)	0.8035 (17)	0.0877 (14)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0267 (3)	0.0428 (3)	0.0322 (3)	0.0018 (2)	0.0104 (2)	−0.0015 (2)
O2	0.0569 (11)	0.0588 (11)	0.0590 (11)	0.0018 (8)	0.0153 (9)	−0.0221 (8)
F1	0.117 (2)	0.160 (2)	0.1197 (19)	0.0660 (17)	0.0356 (16)	0.0554 (17)
O1	0.0301 (7)	0.0530 (9)	0.0395 (8)	−0.0025 (6)	0.0128 (6)	−0.0097 (7)
N1	0.0297 (9)	0.0432 (10)	0.0319 (9)	0.0053 (7)	0.0100 (7)	−0.0046 (7)
C1	0.0344 (11)	0.0534 (14)	0.0345 (11)	−0.0035 (9)	0.0145 (9)	−0.0065 (9)
C3	0.0623 (16)	0.0495 (15)	0.0805 (19)	0.0079 (12)	0.0401 (15)	−0.0068 (13)
N2	0.0341 (10)	0.0566 (12)	0.0448 (10)	0.0024 (8)	0.0127 (8)	0.0117 (9)
C19	0.197 (6)	0.116 (3)	0.183 (5)	−0.055 (3)	0.164 (5)	−0.036 (3)
C20	0.098 (3)	0.134 (4)	0.195 (5)	−0.058 (3)	0.108 (4)	−0.058 (4)
C21	0.0469 (15)	0.108 (2)	0.099 (2)	−0.0154 (15)	0.0406 (16)	−0.0275 (19)
C16	0.0438 (12)	0.0544 (14)	0.0504 (13)	−0.0089 (10)	0.0272 (11)	−0.0132 (11)
N3	0.0382 (10)	0.0433 (10)	0.0495 (10)	0.0031 (8)	0.0231 (8)	−0.0041 (8)
C4	0.0318 (11)	0.0755 (17)	0.0283 (10)	−0.0034 (10)	0.0133 (9)	−0.0064 (10)
C5	0.0392 (13)	0.0812 (19)	0.0388 (12)	0.0100 (12)	0.0113 (10)	0.0077 (12)
C6	0.0586 (17)	0.106 (2)	0.0518 (15)	0.0363 (17)	0.0225 (14)	0.0271 (16)
C7	0.0364 (15)	0.173 (4)	0.0375 (14)	0.0246 (19)	0.0079 (12)	0.0137 (19)
C18	0.168 (5)	0.103 (3)	0.096 (3)	−0.021 (3)	0.090 (3)	0.008 (2)
C17	0.080 (2)	0.096 (2)	0.0561 (17)	−0.0145 (17)	0.0327 (16)	0.0047 (16)
C10	0.0408 (12)	0.0554 (14)	0.0414 (12)	−0.0026 (10)	0.0192 (10)	0.0040 (10)
C15	0.0671 (17)	0.0661 (17)	0.0508 (14)	−0.0006 (13)	0.0321 (13)	−0.0005 (12)
C14	0.081 (2)	0.104 (2)	0.0696 (19)	−0.0008 (18)	0.0532 (18)	0.0014 (17)
C13	0.081 (2)	0.109 (3)	0.092 (2)	−0.0239 (19)	0.055 (2)	0.0053 (19)
C12	0.087 (2)	0.085 (2)	0.116 (3)	−0.0347 (19)	0.064 (2)	−0.021 (2)
C11	0.077 (2)	0.0608 (17)	0.095 (2)	−0.0165 (14)	0.0536 (18)	−0.0173 (15)
C2	0.0450 (14)	0.0756 (19)	0.0676 (17)	0.0094 (13)	0.0120 (13)	0.0298 (14)
C9	0.0389 (13)	0.104 (2)	0.0453 (14)	−0.0153 (13)	0.0144 (11)	−0.0201 (14)
C8	0.0348 (14)	0.173 (4)	0.0450 (16)	−0.0165 (19)	0.0090 (12)	−0.020 (2)

Geometric parameters (Å, º) top

P1—O1	1.4803 (15)	C6—C7	1.362 (5)
P1—N2	1.6271 (19)	C7—C8	1.362 (5)
P1—N3	1.6333 (17)	C7—H7	0.9300
P1—N1	1.6808 (17)	C18—C17	1.521 (4)
O2—C1	1.216 (3)	C18—H18A	0.9700
F1—C6	1.363 (4)	C18—H18B	0.9700
N1—C1	1.368 (3)	C17—H17A	0.9700
N1—H1	0.78 (2)	C17—H17B	0.9700
C1—C4	1.490 (3)	C10—C11	1.515 (3)
C3—N3	1.467 (3)	C10—C15	1.518 (3)
C3—H3A	0.9600	C10—H10	0.9800
C3—H3B	0.9600	C15—C14	1.515 (4)
C3—H3C	0.9600	C15—H15A	0.9700
N2—C2	1.472 (3)	C15—H15B	0.9700
N2—C10	1.476 (3)	C14—C13	1.516 (4)
C19—C18	1.487 (6)	C14—H14A	0.9700
C19—C20	1.518 (7)	C14—H14B	0.9700
C19—H19A	0.9700	C13—C12	1.513 (5)
C19—H19B	0.9700	C13—H13A	0.9700
C20—C21	1.533 (5)	C13—H13B	0.9700
C20—H20A	0.9700	C12—C11	1.519 (4)
C20—H20B	0.9700	C12—H12A	0.9700
C21—C16	1.514 (4)	C12—H12B	0.9700
C21—H21A	0.9700	C11—H11A	0.9700
C21—H21B	0.9700	C11—H11B	0.9700
C16—N3	1.476 (3)	C2—H2A	0.9600
C16—C17	1.520 (4)	C2—H2B	0.9600
C16—H16	0.9800	C2—H2C	0.9600
C4—C5	1.383 (4)	C9—C8	1.386 (4)
C4—C9	1.388 (3)	C9—H9	0.9300
C5—C6	1.377 (3)	C8—H8	0.9300
C5—H5	0.9300

O1—P1—N2	116.35 (10)	C19—C18—C17	111.1 (4)
O1—P1—N3	110.95 (9)	C19—C18—H18A	109.4
N2—P1—N3	105.90 (10)	C17—C18—H18A	109.4
O1—P1—N1	105.93 (9)	C19—C18—H18B	109.4
N2—P1—N1	106.50 (9)	C17—C18—H18B	109.4
N3—P1—N1	111.17 (9)	H18A—C18—H18B	108.0
C1—N1—P1	126.58 (16)	C16—C17—C18	110.9 (3)
C1—N1—H1	118.4 (17)	C16—C17—H17A	109.5
P1—N1—H1	113.4 (16)	C18—C17—H17A	109.5
O2—C1—N1	122.3 (2)	C16—C17—H17B	109.5
O2—C1—C4	121.5 (2)	C18—C17—H17B	109.5
N1—C1—C4	116.18 (19)	H17A—C17—H17B	108.0
N3—C3—H3A	109.5	N2—C10—C11	111.3 (2)
N3—C3—H3B	109.5	N2—C10—C15	114.0 (2)
H3A—C3—H3B	109.5	C11—C10—C15	111.6 (2)
N3—C3—H3C	109.5	N2—C10—H10	106.5
H3A—C3—H3C	109.5	C11—C10—H10	106.5
H3B—C3—H3C	109.5	C15—C10—H10	106.5
C2—N2—C10	117.30 (19)	C14—C15—C10	111.0 (2)
C2—N2—P1	116.26 (16)	C14—C15—H15A	109.4
C10—N2—P1	124.22 (15)	C10—C15—H15A	109.4
C18—C19—C20	110.6 (3)	C14—C15—H15B	109.4
C18—C19—H19A	109.5	C10—C15—H15B	109.4
C20—C19—H19A	109.5	H15A—C15—H15B	108.0
C18—C19—H19B	109.5	C15—C14—C13	111.6 (3)
C20—C19—H19B	109.5	C15—C14—H14A	109.3
H19A—C19—H19B	108.1	C13—C14—H14A	109.3
C19—C20—C21	112.0 (3)	C15—C14—H14B	109.3
C19—C20—H20A	109.2	C13—C14—H14B	109.3
C21—C20—H20A	109.2	H14A—C14—H14B	108.0
C19—C20—H20B	109.2	C12—C13—C14	110.4 (3)
C21—C20—H20B	109.2	C12—C13—H13A	109.6
H20A—C20—H20B	107.9	C14—C13—H13A	109.6
C16—C21—C20	109.7 (3)	C12—C13—H13B	109.6
C16—C21—H21A	109.7	C14—C13—H13B	109.6
C20—C21—H21A	109.7	H13A—C13—H13B	108.1
C16—C21—H21B	109.7	C13—C12—C11	111.3 (3)
C20—C21—H21B	109.7	C13—C12—H12A	109.4
H21A—C21—H21B	108.2	C11—C12—H12A	109.4
N3—C16—C21	112.0 (2)	C13—C12—H12B	109.4
N3—C16—C17	112.4 (2)	C11—C12—H12B	109.4
C21—C16—C17	110.9 (2)	H12A—C12—H12B	108.0
N3—C16—H16	107.1	C10—C11—C12	110.4 (3)
C21—C16—H16	107.1	C10—C11—H11A	109.6
C17—C16—H16	107.1	C12—C11—H11A	109.6
C3—N3—C16	117.01 (18)	C10—C11—H11B	109.6
C3—N3—P1	123.44 (16)	C12—C11—H11B	109.6
C16—N3—P1	118.25 (15)	H11A—C11—H11B	108.1
C5—C4—C9	120.2 (2)	N2—C2—H2A	109.5
C5—C4—C1	122.4 (2)	N2—C2—H2B	109.5
C9—C4—C1	117.4 (2)	H2A—C2—H2B	109.5
C6—C5—C4	117.8 (3)	N2—C2—H2C	109.5
C6—C5—H5	121.1	H2A—C2—H2C	109.5
C4—C5—H5	121.1	H2B—C2—H2C	109.5
C7—C6—F1	119.7 (3)	C8—C9—C4	119.2 (3)
C7—C6—C5	123.4 (3)	C8—C9—H9	120.4
F1—C6—C5	116.9 (3)	C4—C9—H9	120.4
C6—C7—C8	118.0 (3)	C7—C8—C9	121.4 (3)
C6—C7—H7	121.0	C7—C8—H8	119.3
C8—C7—H7	121.0	C9—C8—H8	119.3

O1—P1—N1—C1	−165.46 (18)	N1—C1—C4—C9	154.3 (2)
N2—P1—N1—C1	70.1 (2)	C9—C4—C5—C6	0.1 (3)
N3—P1—N1—C1	−44.8 (2)	C1—C4—C5—C6	−178.2 (2)
P1—N1—C1—O2	−5.7 (3)	C4—C5—C6—C7	−1.4 (4)
P1—N1—C1—C4	173.91 (15)	C4—C5—C6—F1	−179.8 (2)
O1—P1—N2—C2	60.3 (2)	F1—C6—C7—C8	179.8 (3)
N3—P1—N2—C2	−63.5 (2)	C5—C6—C7—C8	1.4 (5)
N1—P1—N2—C2	178.06 (19)	C20—C19—C18—C17	56.5 (5)
O1—P1—N2—C10	−102.28 (19)	N3—C16—C17—C18	−176.7 (3)
N3—P1—N2—C10	133.94 (18)	C21—C16—C17—C18	57.1 (4)
N1—P1—N2—C10	15.5 (2)	C19—C18—C17—C16	−57.4 (4)
C18—C19—C20—C21	−56.3 (5)	C2—N2—C10—C11	63.9 (3)
C19—C20—C21—C16	55.5 (4)	P1—N2—C10—C11	−133.7 (2)
C20—C21—C16—N3	178.0 (3)	C2—N2—C10—C15	−63.3 (3)
C20—C21—C16—C17	−55.6 (4)	P1—N2—C10—C15	99.0 (2)
C21—C16—N3—C3	58.5 (3)	N2—C10—C15—C14	−178.1 (2)
C17—C16—N3—C3	−67.1 (3)	C11—C10—C15—C14	54.8 (3)
C21—C16—N3—P1	−134.1 (2)	C10—C15—C14—C13	−55.0 (3)
C17—C16—N3—P1	100.3 (2)	C15—C14—C13—C12	56.0 (4)
O1—P1—N3—C3	−156.59 (19)	C14—C13—C12—C11	−56.9 (4)
N2—P1—N3—C3	−29.5 (2)	N2—C10—C11—C12	175.9 (3)
N1—P1—N3—C3	85.8 (2)	C15—C10—C11—C12	−55.6 (4)
O1—P1—N3—C16	36.84 (18)	C13—C12—C11—C10	56.8 (4)
N2—P1—N3—C16	163.94 (15)	C5—C4—C9—C8	1.1 (4)
N1—P1—N3—C16	−80.77 (17)	C1—C4—C9—C8	179.5 (2)
O2—C1—C4—C5	152.3 (2)	C6—C7—C8—C9	−0.1 (5)
N1—C1—C4—C5	−27.3 (3)	C4—C9—C8—C7	−1.1 (4)
O2—C1—C4—C9	−26.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.78 (2)	2.04 (2)	2.807 (2)	165 (2)

Symmetry code: (i) −x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₃FN₃O₂P
M_r	409.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	22.6634 (8), 12.9587 (5), 17.6627 (7)
β (°)	119.061 (1)
V (Å³)	4534.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.32 × 0.28 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.658, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	20958, 4228, 3254
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.157, 1.02
No. of reflections	4228
No. of parameters	257
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.93, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XPW (Siemens, 1996), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.78 (2)	2.04 (2)	2.807 (2)	165 (2)

Symmetry code: (i) −x+1/2, −y+3/2, −z.

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
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Volume 67| Part 11| November 2011| Pages o3028-o3029

doi:10.1107/S1600536811043017

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Di­cyclo­hexyl-N′′-(3-fluoro­benzo­yl)-N,N′-di­methyl­phospho­ric tri­amide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

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N,N′-Dicyclohexyl-N′′-(3-fluorobenzoyl)-N,N′-dimethylphosphoric triamide