Diphenyl (cyclo­pentyl­amido)­phospho­nate

Sabbaghi, F.; Pourayoubi, M.; Zargaran, P.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811017028

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1378

doi:10.1107/S1600536811017028

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Diphenyl (cyclopentylamido)phosphonate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi,^b Poorya Zargaran,^b Giuseppe Bruno ^c and Hadi Amiri Rudbari ^c

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^cDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Università di Messina, 98166 Messina, Italy
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 30 March 2011; accepted 5 May 2011; online 11 May 2011)

In the title molecule, C₁₇H₂₀NO₃P, the P atom is bonded in a distorted tetrahedral environment. The dihedral angle between the two phenyl rings is 23.52 (10)°. The phosphoryl and N—H groups are anti with respect to one another. The –CH₂–CH₂–CH₂–CH₂– sequence of atoms in the cyclopentyl ring is disordered over two sets of sites with refined occupancies of 0.574 (10) and 0.426 (10). In the crystal, molecules are linked via N—H⋯O=P hydrogen bonds to form extended chains along [010].

Related literature

For a related structure, see: Pourayoubi et al. (2011 ).

Experimental

Crystal data

C₁₇H₂₀NO₃P
M_r = 317.31
Monoclinic, P 2₁ /c
a = 18.0095 (4) Å
b = 5.3471 (1) Å
c = 17.9387 (4) Å
β = 109.731 (1)°
V = 1626.05 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.5 × 0.4 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.709, T_max = 0.747
139394 measured reflections
3531 independent reflections
3180 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.110
S = 1.08
3531 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯O1ⁱ	0.790 (19)	2.23 (2)	3.0039 (17)	167.7 (19)
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: 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 ); 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/S1600536811017028/lh5228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017028/lh5228Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017028/lh5228Isup3.cml

checkCIF report

Comment top

We have already studied the crystal structure of a diphenyl(amido)phosphonate, (C₆H₅O)₂P(O)(NHCH₂(2-ClC₆H₄) (Pourayoubi et al., 2011). Here, we report the synthesis and crystal structure of title compound.

The P═O, P—O and P—N bond lengths are standard for (amido)phosphonate compounds. The P atom has a distorted tetrahedral configuration (Fig. 1) with the bond angles in the range of 99.72 (6)° [O2–P–O3] to 115.93 (6)° [O1–P–O2]. The phosphoryl group and the N–H unit are in an anti orientation with respect to each other which allows adjacent molecules to form extended chains along [010] via N—H···O(P) hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Pourayoubi et al. (2011).

Experimental top

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of cyclopentylamine (1:2 mole ratio) in chloroform was added at 273 K. After 4 h stirring, the solvent was removed and product was washed with distilled water. Single crystals were obtained from a solution of the title compound in CH₃OH after slow evaporation at room temperature.

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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level. The disorder is not shown.

{[(cyclopentylamino)(phenoxy)phosphoryl]oxy}benzene top

Crystal data top

C₁₇H₂₀NO₃P	F(000) = 672
M_r = 317.31	D_x = 1.296 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9100 reflections
a = 18.0095 (4) Å	θ = 2.3–32.9°
b = 5.3471 (1) Å	µ = 0.18 mm⁻¹
c = 17.9387 (4) Å	T = 296 K
β = 109.731 (1)°	Irregular, colorless
V = 1626.05 (6) Å³	0.5 × 0.4 × 0.2 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3531 independent reflections
Radiation source: fine-focus sealed tube	3180 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −23→23
T_min = 0.709, T_max = 0.747	k = −6→6
139394 measured reflections	l = −22→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0497P)² + 0.5717P] where P = (F_o² + 2F_c²)/3
3531 reflections	(Δ/σ)_max = 0.04
240 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₇H₂₀NO₃P	V = 1626.05 (6) Å³
M_r = 317.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.0095 (4) Å	µ = 0.18 mm⁻¹
b = 5.3471 (1) Å	T = 296 K
c = 17.9387 (4) Å	0.5 × 0.4 × 0.2 mm
β = 109.731 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3531 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3180 reflections with I > 2σ(I)
T_min = 0.709, T_max = 0.747	R_int = 0.021
139394 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.23 e Å⁻³
3531 reflections	Δρ_min = −0.28 e Å⁻³
240 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	Occ. (<1)
C1	0.11088 (11)	0.7234 (4)	0.15643 (15)	0.0736 (6)
H1A	0.1163	0.5834	0.1931	0.088*	0.574 (10)
C2	0.0736 (5)	0.9286 (12)	0.1911 (5)	0.108 (3)	0.574 (10)
H2A	0.0896	0.9112	0.2482	0.130*	0.574 (10)
H2B	0.0900	1.0919	0.1790	0.130*	0.574 (10)
C3	0.0542 (3)	0.6434 (17)	0.0887 (4)	0.105 (3)	0.574 (10)
H3A	0.0622	0.4685	0.0793	0.125*	0.574 (10)
H3B	0.0562	0.7400	0.0437	0.125*	0.574 (10)
C4	−0.0107 (7)	0.901 (2)	0.1558 (11)	0.114 (5)	0.574 (10)
H4A	−0.0339	1.0511	0.1267	0.136*	0.574 (10)
H4B	−0.0344	0.8714	0.1962	0.136*	0.574 (10)
C5	−0.0237 (3)	0.6791 (19)	0.1003 (5)	0.111 (2)	0.574 (10)
H5A	−0.0381	0.5316	0.1238	0.133*	0.574 (10)
H5B	−0.0650	0.7139	0.0503	0.133*	0.574 (10)
H1AA	0.1016	0.5426	0.1550	0.088*	0.426 (10)
C2A	0.0824 (7)	0.830 (4)	0.2078 (6)	0.164 (7)	0.426 (10)
H2A1	0.1020	1.0001	0.2192	0.197*	0.426 (10)
H2A2	0.0978	0.7367	0.2570	0.197*	0.426 (10)
C3A	0.0515 (4)	0.856 (3)	0.0735 (5)	0.121 (4)	0.426 (10)
H3A1	0.0694	1.0221	0.0664	0.146*	0.426 (10)
H3A2	0.0477	0.7548	0.0274	0.146*	0.426 (10)
C4A	−0.0101 (9)	0.830 (4)	0.1673 (13)	0.151 (8)	0.426 (10)
H4A1	−0.0320	0.6723	0.1766	0.181*	0.426 (10)
H4A2	−0.0335	0.9642	0.1882	0.181*	0.426 (10)
C5A	−0.0243 (6)	0.864 (3)	0.0878 (8)	0.131 (4)	0.426 (10)
H5A1	−0.0497	1.0243	0.0711	0.157*	0.426 (10)
H5A2	−0.0590	0.7336	0.0577	0.157*	0.426 (10)
C6	0.38086 (8)	0.6852 (3)	0.24407 (8)	0.0428 (3)
C7	0.37482 (10)	0.8825 (3)	0.29063 (10)	0.0530 (4)
H7	0.3370	1.0062	0.2706	0.064*
C8	0.42607 (11)	0.8939 (4)	0.36780 (11)	0.0642 (4)
H8	0.4225	1.0252	0.4004	0.077*
C9	0.48253 (11)	0.7112 (4)	0.39663 (11)	0.0657 (5)
H9	0.5167	0.7189	0.4487	0.079*
C10	0.48839 (10)	0.5181 (4)	0.34858 (12)	0.0637 (4)
H10	0.5271	0.3968	0.3680	0.076*
C11	0.43704 (9)	0.5027 (3)	0.27138 (10)	0.0534 (4)
H11	0.4405	0.3714	0.2387	0.064*
C12	0.29427 (10)	0.1941 (3)	0.02869 (10)	0.0553 (4)
H12	0.3133	0.1604	0.0827	0.066*
C13	0.31354 (11)	0.0410 (4)	−0.02407 (12)	0.0640 (5)
H13	0.3458	−0.0972	−0.0052	0.077*
C14	0.28593 (12)	0.0892 (4)	−0.10368 (12)	0.0708 (5)
H14	0.2993	−0.0153	−0.1386	0.085*
C15	0.23842 (12)	0.2924 (4)	−0.13150 (10)	0.0706 (5)
H15	0.2194	0.3250	−0.1856	0.085*
C16	0.21843 (10)	0.4497 (4)	−0.08008 (9)	0.0569 (4)
H16	0.1866	0.5886	−0.0991	0.068*
C17	0.24637 (9)	0.3976 (3)	−0.00026 (8)	0.0452 (3)
N	0.19186 (8)	0.7736 (3)	0.16096 (8)	0.0493 (3)
O1	0.23902 (7)	0.31497 (19)	0.17324 (6)	0.0509 (3)
O2	0.33107 (6)	0.6759 (2)	0.16438 (6)	0.0469 (3)
O3	0.22198 (7)	0.5640 (2)	0.04688 (6)	0.0529 (3)
P	0.24508 (2)	0.56130 (6)	0.14026 (2)	0.04116 (13)
H	0.2031 (11)	0.915 (4)	0.1566 (11)	0.057 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0531 (10)	0.0536 (10)	0.1190 (17)	−0.0082 (8)	0.0356 (11)	−0.0161 (11)
C2	0.072 (4)	0.092 (4)	0.175 (8)	−0.012 (2)	0.060 (5)	−0.073 (4)
C3	0.058 (2)	0.141 (5)	0.107 (4)	−0.013 (3)	0.019 (2)	−0.056 (4)
C4	0.072 (5)	0.107 (5)	0.170 (12)	0.018 (4)	0.052 (6)	−0.029 (5)
C5	0.050 (2)	0.147 (6)	0.129 (5)	−0.012 (3)	0.022 (3)	−0.027 (5)
C1A	0.0531 (10)	0.0536 (10)	0.1190 (17)	−0.0082 (8)	0.0356 (11)	−0.0161 (11)
C2A	0.061 (4)	0.38 (2)	0.062 (3)	−0.018 (9)	0.034 (3)	−0.024 (8)
C3A	0.061 (3)	0.210 (12)	0.087 (4)	0.012 (5)	0.018 (3)	0.046 (6)
C4A	0.060 (7)	0.28 (2)	0.128 (10)	−0.052 (9)	0.058 (7)	−0.058 (13)
C5A	0.075 (5)	0.165 (11)	0.148 (8)	0.014 (6)	0.032 (5)	0.035 (9)
C6	0.0413 (7)	0.0400 (7)	0.0492 (7)	−0.0041 (6)	0.0180 (6)	0.0033 (6)
C7	0.0535 (8)	0.0436 (8)	0.0596 (9)	0.0028 (7)	0.0161 (7)	−0.0015 (7)
C8	0.0679 (11)	0.0583 (10)	0.0613 (10)	−0.0034 (8)	0.0153 (8)	−0.0124 (8)
C9	0.0566 (10)	0.0737 (12)	0.0567 (9)	−0.0057 (9)	0.0059 (8)	0.0023 (9)
C10	0.0478 (8)	0.0617 (10)	0.0736 (11)	0.0073 (8)	0.0101 (8)	0.0083 (9)
C11	0.0486 (8)	0.0469 (8)	0.0650 (10)	0.0025 (7)	0.0198 (7)	−0.0024 (7)
C12	0.0640 (9)	0.0521 (9)	0.0489 (8)	0.0033 (7)	0.0180 (7)	−0.0015 (7)
C13	0.0666 (11)	0.0576 (10)	0.0727 (11)	0.0035 (8)	0.0300 (9)	−0.0089 (8)
C14	0.0743 (12)	0.0815 (14)	0.0667 (11)	−0.0092 (10)	0.0370 (10)	−0.0217 (10)
C15	0.0744 (12)	0.0967 (15)	0.0435 (8)	−0.0090 (11)	0.0238 (8)	−0.0067 (9)
C16	0.0545 (9)	0.0676 (11)	0.0463 (8)	−0.0004 (8)	0.0138 (7)	0.0055 (7)
C17	0.0462 (7)	0.0477 (8)	0.0410 (7)	−0.0069 (6)	0.0138 (6)	−0.0034 (6)
N	0.0497 (7)	0.0374 (7)	0.0636 (8)	−0.0043 (5)	0.0227 (6)	−0.0056 (6)
O1	0.0638 (6)	0.0359 (5)	0.0532 (6)	−0.0033 (5)	0.0199 (5)	0.0019 (4)
O2	0.0486 (6)	0.0486 (6)	0.0459 (5)	−0.0031 (4)	0.0190 (4)	0.0027 (4)
O3	0.0659 (7)	0.0478 (6)	0.0416 (5)	0.0109 (5)	0.0136 (5)	0.0021 (4)
P	0.0474 (2)	0.0344 (2)	0.0416 (2)	−0.00097 (14)	0.01477 (15)	0.00036 (13)

Geometric parameters (Å, º) top

C1—C3	1.365 (5)	C6—O2	1.4088 (17)
C1—N	1.458 (2)	C7—C8	1.382 (2)
C1—C2	1.524 (6)	C7—H7	0.9300
C1—H1A	0.9800	C8—C9	1.378 (3)
C2—C4	1.442 (16)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.372 (3)
C2—H2B	0.9700	C9—H9	0.9300
C3—C5	1.499 (7)	C10—C11	1.384 (2)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—H11	0.9300
C4—C5	1.516 (16)	C12—C17	1.377 (2)
C4—H4A	0.9700	C12—C13	1.381 (2)
C4—H4B	0.9700	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.369 (3)
C5—H5B	0.9700	C13—H13	0.9300
C2A—C4A	1.577 (19)	C14—C15	1.369 (3)
C2A—H2A1	0.9700	C14—H14	0.9300
C2A—H2A2	0.9700	C15—C16	1.383 (3)
C3A—C5A	1.472 (12)	C15—H15	0.9300
C3A—H3A1	0.9700	C16—C17	1.376 (2)
C3A—H3A2	0.9700	C16—H16	0.9300
C4A—C5A	1.37 (3)	C17—O3	1.3968 (18)
C4A—H4A1	0.9700	N—P	1.6078 (14)
C4A—H4A2	0.9700	N—H	0.793 (19)
C5A—H5A1	0.9700	O1—P	1.4630 (11)
C5A—H5A2	0.9700	O2—P	1.5839 (10)
C6—C11	1.372 (2)	O3—P	1.5838 (11)
C6—C7	1.373 (2)

C3—C1—N	122.8 (3)	C11—C6—C7	122.00 (15)
C3—C1—C2	106.8 (4)	C11—C6—O2	118.51 (13)
N—C1—C2	114.5 (3)	C7—C6—O2	119.39 (13)
C3—C1—H1A	103.5	C6—C7—C8	118.69 (15)
N—C1—H1A	103.5	C6—C7—H7	120.7
C2—C1—H1A	103.5	C8—C7—H7	120.7
C4—C2—C1	106.9 (6)	C9—C8—C7	120.23 (17)
C4—C2—H2A	110.3	C9—C8—H8	119.9
C1—C2—H2A	110.4	C7—C8—H8	119.9
C4—C2—H2B	110.3	C10—C9—C8	120.07 (17)
C1—C2—H2B	110.3	C10—C9—H9	120.0
H2A—C2—H2B	108.6	C8—C9—H9	120.0
C1—C3—C5	106.9 (4)	C9—C10—C11	120.43 (17)
C1—C3—H3A	110.3	C9—C10—H10	119.8
C5—C3—H3A	110.3	C11—C10—H10	119.8
C1—C3—H3B	110.3	C6—C11—C10	118.57 (16)
C5—C3—H3B	110.3	C6—C11—H11	120.7
H3A—C3—H3B	108.6	C10—C11—H11	120.7
C2—C4—C5	105.9 (6)	C17—C12—C13	118.71 (16)
C2—C4—H4A	110.6	C17—C12—H12	120.6
C5—C4—H4A	110.5	C13—C12—H12	120.6
C2—C4—H4B	110.5	C14—C13—C12	121.09 (18)
C5—C4—H4B	110.6	C14—C13—H13	119.5
H4A—C4—H4B	108.7	C12—C13—H13	119.5
C3—C5—C4	104.2 (6)	C13—C14—C15	119.48 (17)
C3—C5—H5A	110.9	C13—C14—H14	120.3
C4—C5—H5A	110.9	C15—C14—H14	120.3
C3—C5—H5B	110.9	C14—C15—C16	120.75 (17)
C4—C5—H5B	110.9	C14—C15—H15	119.6
H5A—C5—H5B	108.9	C16—C15—H15	119.6
C4A—C2A—H2A1	110.5	C17—C16—C15	118.99 (18)
C4A—C2A—H2A2	110.6	C17—C16—H16	120.5
H2A1—C2A—H2A2	108.7	C15—C16—H16	120.5
C5A—C3A—H3A1	111.4	C12—C17—C16	120.99 (15)
C5A—C3A—H3A2	111.3	C12—C17—O3	124.08 (13)
H3A1—C3A—H3A2	109.2	C16—C17—O3	114.93 (14)
C5A—C4A—C2A	106.1 (12)	C1—N—P	121.36 (12)
C5A—C4A—H4A1	110.5	C1—N—H	117.0 (14)
C2A—C4A—H4A1	110.5	P—N—H	117.3 (14)
C5A—C4A—H4A2	110.5	C6—O2—P	121.30 (8)
C2A—C4A—H4A2	110.5	C17—O3—P	127.62 (10)
H4A1—C4A—H4A2	108.7	O1—P—O2	115.93 (6)
C4A—C5A—C3A	108.6 (9)	O1—P—O3	114.03 (6)
C4A—C5A—H5A1	110.0	O2—P—O3	99.72 (6)
C3A—C5A—H5A1	109.9	O1—P—N	114.24 (7)
C4A—C5A—H5A2	110.0	O2—P—N	105.55 (6)
C3A—C5A—H5A2	110.0	O3—P—N	105.88 (7)
H5A1—C5A—H5A2	108.4

C3—C1—C2—C4	18.7 (10)	C13—C12—C17—C16	−0.5 (2)
N—C1—C2—C4	158.1 (8)	C13—C12—C17—O3	179.15 (15)
N—C1—C3—C5	−165.1 (4)	C15—C16—C17—C12	0.8 (3)
C2—C1—C3—C5	−29.9 (7)	C15—C16—C17—O3	−178.89 (15)
C1—C2—C4—C5	0.3 (13)	C3—C1—N—P	−57.8 (5)
C1—C3—C5—C4	29.8 (11)	C2—C1—N—P	170.1 (4)
C2—C4—C5—C3	−17.2 (14)	C11—C6—O2—P	98.41 (14)
C2A—C4A—C5A—C3A	7 (2)	C7—C6—O2—P	−85.20 (15)
C11—C6—C7—C8	−1.3 (2)	C12—C17—O3—P	2.0 (2)
O2—C6—C7—C8	−177.58 (15)	C16—C17—O3—P	−178.33 (11)
C6—C7—C8—C9	0.7 (3)	C6—O2—P—O1	−49.72 (12)
C7—C8—C9—C10	0.4 (3)	C6—O2—P—O3	−172.58 (10)
C8—C9—C10—C11	−1.1 (3)	C6—O2—P—N	77.80 (12)
C7—C6—C11—C10	0.7 (2)	C17—O3—P—O1	−46.75 (15)
O2—C6—C11—C10	177.00 (14)	C17—O3—P—O2	77.45 (13)
C9—C10—C11—C6	0.5 (3)	C17—O3—P—N	−173.19 (12)
C17—C12—C13—C14	0.1 (3)	C1—N—P—O1	−43.33 (18)
C12—C13—C14—C15	0.0 (3)	C1—N—P—O2	−171.87 (15)
C13—C14—C15—C16	0.3 (3)	C1—N—P—O3	82.99 (16)
C14—C15—C16—C17	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O1ⁱ	0.790 (19)	2.23 (2)	3.0039 (17)	167.7 (19)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀NO₃P
M_r	317.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.0095 (4), 5.3471 (1), 17.9387 (4)
β (°)	109.731 (1)
V (Å³)	1626.05 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.5 × 0.4 × 0.2

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.709, 0.747
No. of measured, independent and observed [I > 2σ(I)] reflections	139394, 3531, 3180
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.08
No. of reflections	3531
No. of parameters	240
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), 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
N—H···O1ⁱ	0.790 (19)	2.23 (2)	3.0039 (17)	167.7 (19)

Symmetry code: (i) x, y+1, z.

Acknowledgements

Support of this investigation by Zanjan Branch, Islamic Azad University, is gratefully acknowledged.

References

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