Diphenyl (cyclo-pentyl-amido)-phospho-nate.

In the title mol-ecule, C(17)H(20)NO(3)P, the P atom is bonded in a distorted tetra-hedral 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 -CH(2)-CH(2)-CH(2)-CH(2)- sequence of atoms in the cyclo-pentyl ring is disordered over two sets of sites with refined occupancies of 0.574 (10) and 0.426 (10). In the crystal, mol-ecules 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 = 317.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.08

3531 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017028/lh5228sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811017028/lh5228Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H20NO3P	F(000) = 672
Mr = 317.31	Dx = 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

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

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(Fo2) + (0.0497P)2 + 0.5717P] where P = (Fo2 + 2Fc2)/3
3531 reflections	(Δ/σ)max = 0.04
240 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)*

	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)

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)

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)

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) .