O-Phenyl (cyclo-hexyl-amido)(p-tolyl-amido)-phosphinate.

In the title mol-ecule, C(19)H(25)N(2)O(2)P, the P atom is bonded in a distorted tetra-hedral environment. The dihedral angle between the two phenyl rings is 89.09 (8)°. The methyl H atoms are disordered over two sets of sites with equal occupancy. The O atom of the P=O group acts as a double hydrogen-bond acceptor of the type (N-H)(2)⋯(O=)P-, forming R(2) (2)(8) rings which are further linked into chains along [010].

Related literature

For background to mixed-amido phosphinates, see: Pourayoubi et al. (2007 ▶). For double hydrogen-bond acceptors, see: Steiner (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H25N2O2P

M = 344.38

Monoclinic,

a = 15.5575 (4) Å

b = 7.7006 (3) Å

c = 16.1717 (4) Å

β = 108.9709 (17)°

V = 1832.17 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 173 K

0.16 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.974, T max = 0.984

13695 measured reflections

4172 independent reflections

3069 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.124

S = 1.06

4172 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018502/lh5250sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018502/lh5250Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018502/lh5250Isup3.cml

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

C19H25N2O2P	F(000) = 736
Mr = 344.38	Dx = 1.248 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7090 reflections
a = 15.5575 (4) Å	θ = 3.0–27.5°
b = 7.7006 (3) Å	µ = 0.16 mm−1
c = 16.1717 (4) Å	T = 173 K
β = 108.9709 (17)°	Prism, colorless
V = 1832.17 (10) Å3	0.16 × 0.14 × 0.10 mm
Z = 4

Nonius KappaCCD diffractometer	4172 independent reflections
Radiation source: fine-focus sealed tube	3069 reflections with I > 2σ(I)
graphite	Rint = 0.070
ω and φ scans	θmax = 27.6°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −20→20
Tmin = 0.974, Tmax = 0.984	k = −9→9
13695 measured reflections	l = −20→21

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0234P)2 + 2.302P] where P = (Fo2 + 2Fc2)/3
4172 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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	0.73253 (4)	0.16106 (8)	0.67651 (4)	0.02345 (15)
O1	0.71919 (11)	0.1863 (2)	0.76217 (10)	0.0283 (4)
O2	0.64631 (10)	0.0713 (2)	0.60756 (10)	0.0285 (4)
N1	0.80997 (14)	0.0288 (3)	0.66811 (13)	0.0273 (4)
H1N	0.8023 (17)	−0.070 (4)	0.6810 (17)	0.033*
N2	0.75059 (13)	0.3485 (3)	0.63724 (12)	0.0247 (4)
H2N	0.7553 (17)	0.434 (3)	0.6707 (16)	0.030*
C1	0.90574 (15)	0.0755 (3)	0.68466 (15)	0.0261 (5)
H1	0.9074	0.1999	0.6674	0.031*
C2	0.94454 (16)	−0.0325 (4)	0.62658 (16)	0.0335 (6)
H2A	0.9434	−0.1568	0.6419	0.040*
H2B	0.9063	−0.0178	0.5647	0.040*
C3	1.04166 (17)	0.0216 (4)	0.63741 (18)	0.0402 (6)
H3A	1.0666	−0.0555	0.6018	0.048*
H3B	1.0418	0.1418	0.6158	0.048*
C4	1.10170 (18)	0.0119 (4)	0.73256 (18)	0.0432 (7)
H4A	1.1089	−0.1110	0.7515	0.052*
H4B	1.1627	0.0584	0.7382	0.052*
C5	1.06180 (17)	0.1142 (4)	0.79143 (17)	0.0410 (7)
H5A	1.0629	0.2395	0.7781	0.049*
H5B	1.0998	0.0965	0.8531	0.049*
C6	0.96421 (16)	0.0595 (4)	0.77984 (15)	0.0329 (6)
H6A	0.9635	−0.0622	0.7994	0.040*
H6B	0.9391	0.1340	0.8164	0.040*
C7	0.77827 (15)	0.3772 (3)	0.56278 (14)	0.0236 (5)
C8	0.75810 (16)	0.2609 (3)	0.49355 (15)	0.0275 (5)
H8	0.7229	0.1600	0.4936	0.033*
C9	0.79007 (16)	0.2939 (3)	0.42412 (15)	0.0299 (5)
H9	0.7767	0.2132	0.3772	0.036*
C10	0.84044 (17)	0.4393 (3)	0.42080 (16)	0.0333 (6)
C11	0.85877 (19)	0.5555 (4)	0.49027 (18)	0.0396 (6)
H11	0.8929	0.6574	0.4896	0.048*
C12	0.82810 (17)	0.5252 (3)	0.56052 (16)	0.0320 (6)
H12	0.8413	0.6063	0.6073	0.038*
C13	0.8741 (2)	0.4732 (4)	0.34463 (18)	0.0489 (8)
H13A	0.9083	0.5823	0.3543	0.073*	0.50
H13B	0.8221	0.4817	0.2907	0.073*	0.50
H13C	0.9136	0.3776	0.3395	0.073*	0.50
H13D	0.8544	0.3788	0.3020	0.073*	0.50
H13E	0.9406	0.4794	0.3656	0.073*	0.50
H13F	0.8491	0.5835	0.3168	0.073*	0.50
C14	0.55737 (15)	0.1271 (3)	0.59596 (15)	0.0264 (5)
C15	0.51721 (17)	0.2434 (3)	0.52978 (15)	0.0328 (6)
H15	0.5507	0.2917	0.4956	0.039*
C16	0.42679 (18)	0.2884 (4)	0.51410 (17)	0.0401 (6)
H16	0.3980	0.3682	0.4687	0.048*
C17	0.37857 (18)	0.2181 (4)	0.56396 (18)	0.0412 (7)
H17	0.3169	0.2497	0.5532	0.049*
C18	0.42027 (17)	0.1015 (4)	0.62967 (17)	0.0390 (6)
H18	0.3866	0.0522	0.6635	0.047*
C19	0.51073 (17)	0.0554 (3)	0.64696 (16)	0.0336 (6)
H19	0.5397	−0.0235	0.6927	0.040*

	U11	U22	U33	U12	U13	U23
P1	0.0297 (3)	0.0183 (3)	0.0243 (3)	−0.0017 (2)	0.0115 (2)	−0.0006 (2)
O1	0.0396 (9)	0.0227 (9)	0.0261 (8)	−0.0002 (7)	0.0155 (7)	0.0006 (7)
O2	0.0299 (8)	0.0265 (9)	0.0315 (9)	−0.0031 (7)	0.0132 (7)	−0.0050 (7)
N1	0.0316 (10)	0.0179 (10)	0.0344 (11)	−0.0028 (9)	0.0136 (9)	0.0009 (9)
N2	0.0356 (11)	0.0199 (10)	0.0226 (10)	−0.0011 (9)	0.0149 (8)	−0.0012 (8)
C1	0.0284 (11)	0.0216 (12)	0.0303 (12)	−0.0008 (10)	0.0122 (10)	0.0010 (10)
C2	0.0347 (13)	0.0365 (15)	0.0310 (13)	0.0007 (11)	0.0128 (11)	−0.0065 (11)
C3	0.0386 (14)	0.0436 (17)	0.0460 (16)	0.0003 (13)	0.0242 (13)	−0.0058 (13)
C4	0.0310 (13)	0.0441 (17)	0.0534 (17)	0.0016 (12)	0.0124 (13)	−0.0047 (14)
C5	0.0353 (14)	0.0447 (17)	0.0396 (15)	−0.0025 (13)	0.0074 (12)	−0.0071 (13)
C6	0.0382 (14)	0.0329 (14)	0.0297 (12)	0.0000 (11)	0.0138 (11)	−0.0028 (11)
C7	0.0270 (11)	0.0205 (12)	0.0235 (11)	0.0027 (9)	0.0085 (9)	0.0024 (9)
C8	0.0295 (12)	0.0238 (12)	0.0292 (12)	−0.0008 (10)	0.0095 (10)	−0.0009 (10)
C9	0.0355 (13)	0.0304 (14)	0.0240 (11)	0.0017 (11)	0.0098 (10)	−0.0043 (10)
C10	0.0402 (14)	0.0335 (14)	0.0322 (13)	0.0040 (12)	0.0201 (11)	0.0041 (11)
C11	0.0514 (16)	0.0282 (15)	0.0486 (16)	−0.0080 (12)	0.0290 (13)	−0.0009 (12)
C12	0.0444 (14)	0.0220 (12)	0.0342 (13)	−0.0069 (11)	0.0190 (11)	−0.0049 (10)
C13	0.0657 (19)	0.0486 (19)	0.0457 (16)	−0.0036 (16)	0.0366 (15)	−0.0001 (14)
C14	0.0300 (12)	0.0219 (12)	0.0292 (12)	−0.0046 (10)	0.0122 (10)	−0.0062 (10)
C15	0.0398 (14)	0.0319 (14)	0.0290 (12)	−0.0039 (11)	0.0142 (11)	−0.0003 (11)
C16	0.0409 (15)	0.0403 (16)	0.0347 (14)	0.0051 (13)	0.0063 (12)	0.0006 (12)
C17	0.0308 (13)	0.0462 (17)	0.0460 (16)	0.0017 (12)	0.0115 (12)	−0.0098 (14)
C18	0.0383 (14)	0.0424 (17)	0.0433 (15)	−0.0078 (13)	0.0229 (12)	−0.0044 (13)
C19	0.0401 (14)	0.0291 (14)	0.0334 (13)	−0.0031 (11)	0.0146 (11)	0.0011 (11)

P1—O1	1.4788 (16)	C7—C8	1.388 (3)
P1—O2	1.5961 (17)	C8—C9	1.391 (3)
P1—N1	1.617 (2)	C8—H8	0.9500
P1—N2	1.637 (2)	C9—C10	1.378 (4)
O2—C14	1.402 (3)	C9—H9	0.9500
N1—C1	1.470 (3)	C10—C11	1.391 (4)
N1—H1N	0.81 (3)	C10—C13	1.510 (3)
N2—C7	1.422 (3)	C11—C12	1.387 (3)
N2—H2N	0.84 (3)	C11—H11	0.9500
C1—C6	1.517 (3)	C12—H12	0.9500
C1—C2	1.519 (3)	C13—H13A	0.9800
C1—H1	1.0000	C13—H13B	0.9800
C2—C3	1.522 (3)	C13—H13C	0.9800
C2—H2A	0.9900	C13—H13D	0.9800
C2—H2B	0.9900	C13—H13E	0.9800
C3—C4	1.520 (4)	C13—H13F	0.9800
C3—H3A	0.9900	C14—C15	1.379 (3)
C3—H3B	0.9900	C14—C19	1.379 (3)
C4—C5	1.515 (4)	C15—C16	1.390 (4)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—C17	1.378 (4)
C5—C6	1.527 (3)	C16—H16	0.9500
C5—H5A	0.9900	C17—C18	1.381 (4)
C5—H5B	0.9900	C17—H17	0.9500
C6—H6A	0.9900	C18—C19	1.389 (4)
C6—H6B	0.9900	C18—H18	0.9500
C7—C12	1.386 (3)	C19—H19	0.9500
O1—P1—O2	111.68 (9)	C7—C8—H8	120.4
O1—P1—N1	119.80 (10)	C9—C8—H8	120.4
O2—P1—N1	98.55 (10)	C10—C9—C8	122.5 (2)
O1—P1—N2	109.97 (10)	C10—C9—H9	118.8
O2—P1—N2	108.77 (10)	C8—C9—H9	118.8
N1—P1—N2	107.23 (10)	C9—C10—C11	117.5 (2)
C14—O2—P1	121.97 (14)	C9—C10—C13	121.7 (2)
C1—N1—P1	124.70 (17)	C11—C10—C13	120.9 (2)
C1—N1—H1N	114.1 (19)	C12—C11—C10	121.2 (2)
P1—N1—H1N	113.3 (19)	C12—C11—H11	119.4
C7—N2—P1	127.10 (16)	C10—C11—H11	119.4
C7—N2—H2N	115.9 (18)	C11—C12—C7	120.3 (2)
P1—N2—H2N	115.5 (17)	C11—C12—H12	119.9
N1—C1—C6	113.73 (19)	C7—C12—H12	119.9
N1—C1—C2	109.64 (19)	C10—C13—H13A	109.5
C6—C1—C2	110.8 (2)	C10—C13—H13B	109.5
N1—C1—H1	107.5	H13A—C13—H13B	109.5
C6—C1—H1	107.5	C10—C13—H13C	109.5
C2—C1—H1	107.5	H13A—C13—H13C	109.5
C3—C2—C1	111.0 (2)	H13B—C13—H13C	109.5
C3—C2—H2A	109.4	C10—C13—H13D	109.5
C1—C2—H2A	109.4	H13A—C13—H13D	141.1
C3—C2—H2B	109.4	H13B—C13—H13D	56.3
C1—C2—H2B	109.4	H13C—C13—H13D	56.3
H2A—C2—H2B	108.0	C10—C13—H13E	109.5
C4—C3—C2	111.3 (2)	H13A—C13—H13E	56.3
C4—C3—H3A	109.4	H13B—C13—H13E	141.1
C2—C3—H3A	109.4	H13C—C13—H13E	56.3
C4—C3—H3B	109.4	H13D—C13—H13E	109.5
C2—C3—H3B	109.4	C10—C13—H13F	109.5
H3A—C3—H3B	108.0	H13A—C13—H13F	56.3
C5—C4—C3	111.6 (2)	H13B—C13—H13F	56.3
C5—C4—H4A	109.3	H13C—C13—H13F	141.1
C3—C4—H4A	109.3	H13D—C13—H13F	109.5
C5—C4—H4B	109.3	H13E—C13—H13F	109.5
C3—C4—H4B	109.3	C15—C14—C19	122.0 (2)
H4A—C4—H4B	108.0	C15—C14—O2	118.8 (2)
C4—C5—C6	111.9 (2)	C19—C14—O2	119.0 (2)
C4—C5—H5A	109.2	C14—C15—C16	118.7 (2)
C6—C5—H5A	109.2	C14—C15—H15	120.7
C4—C5—H5B	109.2	C16—C15—H15	120.7
C6—C5—H5B	109.2	C17—C16—C15	120.4 (3)
H5A—C5—H5B	107.9	C17—C16—H16	119.8
C1—C6—C5	110.2 (2)	C15—C16—H16	119.8
C1—C6—H6A	109.6	C16—C17—C18	119.8 (2)
C5—C6—H6A	109.6	C16—C17—H17	120.1
C1—C6—H6B	109.6	C18—C17—H17	120.1
C5—C6—H6B	109.6	C17—C18—C19	120.9 (2)
H6A—C6—H6B	108.1	C17—C18—H18	119.6
C12—C7—C8	119.4 (2)	C19—C18—H18	119.6
C12—C7—N2	118.5 (2)	C14—C19—C18	118.2 (2)
C8—C7—N2	122.1 (2)	C14—C19—H19	120.9
C7—C8—C9	119.1 (2)	C18—C19—H19	120.9
O1—P1—O2—C14	46.41 (19)	C12—C7—C8—C9	1.3 (3)
N1—P1—O2—C14	173.31 (17)	N2—C7—C8—C9	−177.7 (2)
N2—P1—O2—C14	−75.14 (18)	C7—C8—C9—C10	−0.7 (4)
O1—P1—N1—C1	−86.5 (2)	C8—C9—C10—C11	−0.2 (4)
O2—P1—N1—C1	152.36 (18)	C8—C9—C10—C13	−179.7 (2)
N2—P1—N1—C1	39.6 (2)	C9—C10—C11—C12	0.5 (4)
O1—P1—N2—C7	170.92 (18)	C13—C10—C11—C12	−180.0 (3)
O2—P1—N2—C7	−66.5 (2)	C10—C11—C12—C7	0.1 (4)
N1—P1—N2—C7	39.1 (2)	C8—C7—C12—C11	−1.0 (4)
P1—N1—C1—C6	86.5 (2)	N2—C7—C12—C11	178.0 (2)
P1—N1—C1—C2	−148.82 (18)	P1—O2—C14—C15	95.6 (2)
N1—C1—C2—C3	176.0 (2)	P1—O2—C14—C19	−88.8 (2)
C6—C1—C2—C3	−57.7 (3)	C19—C14—C15—C16	−0.3 (4)
C1—C2—C3—C4	55.5 (3)	O2—C14—C15—C16	175.2 (2)
C2—C3—C4—C5	−53.6 (3)	C14—C15—C16—C17	0.1 (4)
C3—C4—C5—C6	54.0 (3)	C15—C16—C17—C18	−0.3 (4)
N1—C1—C6—C5	−178.7 (2)	C16—C17—C18—C19	0.7 (4)
C2—C1—C6—C5	57.2 (3)	C15—C14—C19—C18	0.7 (4)
C4—C5—C6—C1	−55.6 (3)	O2—C14—C19—C18	−174.8 (2)
P1—N2—C7—C12	−151.43 (19)	C17—C18—C19—C14	−0.9 (4)
P1—N2—C7—C8	27.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.81 (3)	2.16 (3)	2.961 (3)	169 (3)
N2—H2N···O1ii	0.84 (3)	2.20 (3)	3.023 (3)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.81 (3)	2.16 (3)	2.961 (3)	169 (3)
N2—H2N⋯O1ii	0.84 (3)	2.20 (3)	3.023 (3)	167 (2)

Symmetry codes: (i) ; (ii) .