N-Benzyl-P-(2-ethyl-phen-yl)-P-phenyl-phosphinic amide.

In the crystal structure of the title compound, C(21)H(22)NOP, the amine H atom is involved in N-H⋯O hydrogen-bonding inter-actions, resulting in chains along the c axis. The crystal lattice is consolidated by weak inter-molecular C-H⋯π inter-actions.

Related literature

For the uses of phosphinamides, see: Wuts & Greene (2006 ▶); Burgos et al. (2008 ▶); Popovici et al. (2010 ▶). For related compounds, see: Priya et al. (2005 ▶); Fei et al. (2004 ▶); Gaw et al. (1999 ▶).

Experimental

Crystal data

C21H22NOP

M = 335.37

Monoclinic,

a = 12.9259 (3) Å

b = 15.7098 (3) Å

c = 9.1007 (2) Å

β = 107.578 (1)°

V = 1761.73 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.42 mm−1

T = 100 K

0.48 × 0.08 × 0.02 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.549, T max = 0.972

13806 measured reflections

2946 independent reflections

2772 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.05

2946 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049014/hg5139sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049014/hg5139Isup2.hkl

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

C21H22NOP	F(000) = 712
Mr = 335.37	Dx = 1.264 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 14165 reflections
a = 12.9259 (3) Å	θ = 3.6–66.2°
b = 15.7098 (3) Å	µ = 1.42 mm−1
c = 9.1007 (2) Å	T = 100 K
β = 107.578 (1)°	Needle, colourless
V = 1761.73 (7) Å3	0.48 × 0.08 × 0.02 mm
Z = 4

Bruker X8 APEXII 4K KappaCCD diffractometer	2772 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 66.2°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
Tmin = 0.549, Tmax = 0.972	k = −18→18
13806 measured reflections	l = −9→10
2946 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0573P)2 + 1.6926P] where P = (Fo2 + 2Fc2)/3
2946 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.57 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.>>> The Following Model ALERTS were generated - (Acta-Mode) <<< Format: alert-number_ALERT_alert-type_alert-level text 414_ALERT_2_C Short Intra D—H..H—X H1.. H6.. 1.98 A ng. 414_ALERT_2_C Short Intra D—H..H—X H1.. H20A.. 1.96 A ng. 911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.594 147 793_ALERT_4_G The Model has Chirality at P1 (Verify) ···. R 802_ALERT_4_G CIF Input Record(s) with more than 80 Characters ! 909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 89 Perc. Noted:

	x	y	z	Uiso*/Ueq
C1	0.98660 (15)	0.18270 (12)	0.8933 (2)	0.0197 (4)
C2	1.09281 (16)	0.21294 (13)	0.9436 (2)	0.0250 (4)
H2	1.1152	0.2556	0.8857	0.03*
C3	1.16615 (17)	0.18153 (14)	1.0770 (2)	0.0286 (5)
H3	1.2384	0.2026	1.1098	0.034*
C4	1.13436 (16)	0.11951 (13)	1.1627 (2)	0.0258 (5)
H4	1.1847	0.0976	1.2538	0.031*
C5	1.02898 (16)	0.08980 (13)	1.1148 (2)	0.0245 (4)
H5	1.0065	0.0477	1.1736	0.029*
C6	0.95550 (15)	0.12126 (12)	0.9808 (2)	0.0222 (4)
H6	0.8831	0.1004	0.9489	0.027*
C7	0.91011 (15)	0.21860 (13)	0.7457 (2)	0.0236 (4)
H7A	0.9099	0.2815	0.7531	0.028*
H7B	0.9373	0.2033	0.6585	0.028*
C8	0.75770 (15)	0.10376 (13)	0.4367 (2)	0.0215 (4)
C9	0.82914 (15)	0.04046 (13)	0.5135 (2)	0.0248 (4)
H9	0.8565	0.0413	0.6228	0.03*
C10	0.86062 (17)	−0.02365 (14)	0.4320 (3)	0.0325 (5)
H10	0.9095	−0.0665	0.4852	0.039*
C11	0.82036 (19)	−0.02514 (16)	0.2719 (3)	0.0382 (6)
H11	0.8413	−0.0692	0.2153	0.046*
C12	0.7494 (2)	0.03806 (16)	0.1952 (3)	0.0383 (6)
H12	0.7225	0.0372	0.0858	0.046*
C13	0.71770 (17)	0.10198 (14)	0.2759 (2)	0.0295 (5)
H13	0.6688	0.1447	0.2223	0.035*
C14	0.58144 (16)	0.17310 (13)	0.5493 (2)	0.0237 (4)
C15	0.50497 (17)	0.23235 (14)	0.4639 (2)	0.0291 (5)
H15	0.528	0.2767	0.41	0.035*
C16	0.39696 (17)	0.22687 (15)	0.4572 (3)	0.0338 (5)
H16	0.346	0.2675	0.4004	0.041*
C17	0.36414 (17)	0.16148 (15)	0.5343 (3)	0.0313 (5)
H17	0.2899	0.1569	0.5296	0.038*
C18	0.43787 (16)	0.10283 (14)	0.6179 (2)	0.0278 (5)
H18	0.4133	0.0584	0.6699	0.033*
C19	0.54819 (16)	0.10689 (13)	0.6284 (2)	0.0247 (4)
C20	0.62697 (16)	0.04282 (14)	0.7234 (2)	0.0288 (5)
H20A	0.6801	0.0735	0.8083	0.035*
H20B	0.6675	0.0175	0.6578	0.035*
C21	0.57827 (18)	−0.02982 (15)	0.7939 (3)	0.0341 (5)
H21A	0.5395	−0.0061	0.8619	0.051*
H21B	0.6366	−0.0673	0.8533	0.051*
H21C	0.5276	−0.0625	0.7113	0.051*
N1	0.79874 (12)	0.18732 (10)	0.71386 (18)	0.0206 (4)
H1	0.776	0.1667	0.7886	0.025*
O1	0.71769 (11)	0.27168 (9)	0.45065 (15)	0.0254 (3)
P1	0.71741 (4)	0.19123 (3)	0.53744 (5)	0.01919 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0195 (9)	0.0215 (9)	0.0192 (10)	0.0013 (7)	0.0074 (8)	−0.0021 (7)
C2	0.0216 (10)	0.0272 (10)	0.0265 (10)	−0.0034 (8)	0.0078 (8)	0.0019 (8)
C3	0.0194 (10)	0.0337 (11)	0.0295 (11)	−0.0023 (8)	0.0024 (8)	−0.0006 (9)
C4	0.0238 (10)	0.0275 (10)	0.0227 (10)	0.0055 (8)	0.0022 (8)	0.0010 (8)
C5	0.0272 (10)	0.0225 (10)	0.0244 (10)	0.0022 (8)	0.0085 (8)	0.0032 (8)
C6	0.0201 (9)	0.0229 (10)	0.0233 (10)	−0.0007 (8)	0.0060 (8)	0.0000 (8)
C7	0.0185 (9)	0.0301 (10)	0.0221 (10)	−0.0039 (8)	0.0062 (8)	0.0042 (8)
C8	0.0194 (9)	0.0270 (10)	0.0203 (9)	−0.0050 (8)	0.0093 (7)	0.0004 (8)
C9	0.0204 (10)	0.0307 (11)	0.0256 (10)	−0.0017 (8)	0.0102 (8)	0.0004 (8)
C10	0.0240 (11)	0.0325 (12)	0.0458 (13)	−0.0015 (9)	0.0177 (10)	−0.0032 (10)
C11	0.0390 (13)	0.0396 (13)	0.0462 (14)	−0.0108 (10)	0.0282 (11)	−0.0169 (11)
C12	0.0442 (13)	0.0490 (14)	0.0256 (11)	−0.0133 (11)	0.0164 (10)	−0.0079 (10)
C13	0.0327 (11)	0.0356 (12)	0.0211 (10)	−0.0059 (9)	0.0094 (9)	0.0003 (9)
C14	0.0206 (10)	0.0307 (11)	0.0202 (10)	−0.0018 (8)	0.0070 (8)	−0.0044 (8)
C15	0.0276 (11)	0.0306 (11)	0.0296 (11)	0.0007 (9)	0.0097 (9)	0.0033 (9)
C16	0.0239 (11)	0.0370 (12)	0.0372 (12)	0.0061 (9)	0.0043 (9)	0.0032 (10)
C17	0.0210 (10)	0.0375 (12)	0.0354 (12)	−0.0020 (9)	0.0086 (9)	−0.0041 (10)
C18	0.0224 (10)	0.0323 (11)	0.0305 (11)	−0.0058 (9)	0.0106 (8)	−0.0067 (9)
C19	0.0231 (10)	0.0285 (11)	0.0222 (10)	−0.0022 (8)	0.0064 (8)	−0.0047 (8)
C20	0.0239 (10)	0.0356 (12)	0.0278 (11)	−0.0026 (9)	0.0091 (8)	0.0006 (9)
C21	0.0308 (11)	0.0370 (12)	0.0338 (12)	−0.0036 (9)	0.0086 (9)	0.0053 (10)
N1	0.0180 (8)	0.0269 (9)	0.0180 (8)	−0.0029 (6)	0.0069 (7)	0.0036 (6)
O1	0.0255 (7)	0.0291 (8)	0.0218 (7)	0.0018 (6)	0.0075 (6)	0.0047 (6)
P1	0.0162 (3)	0.0251 (3)	0.0166 (3)	−0.00091 (18)	0.00544 (19)	0.00211 (18)

C1—C6	1.386 (3)	C12—C13	1.378 (3)
C1—C2	1.393 (3)	C12—H12	0.95
C1—C7	1.516 (3)	C13—H13	0.95
C2—C3	1.386 (3)	C14—C19	1.404 (3)
C2—H2	0.95	C14—C15	1.409 (3)
C3—C4	1.386 (3)	C14—P1	1.816 (2)
C3—H3	0.95	C15—C16	1.382 (3)
C4—C5	1.380 (3)	C15—H15	0.95
C4—H4	0.95	C16—C17	1.381 (3)
C5—C6	1.391 (3)	C16—H16	0.95
C5—H5	0.95	C17—C18	1.378 (3)
C6—H6	0.95	C17—H17	0.95
C7—N1	1.465 (2)	C18—C19	1.402 (3)
C7—H7A	0.99	C18—H18	0.95
C7—H7B	0.99	C19—C20	1.505 (3)
C8—C9	1.393 (3)	C20—C21	1.534 (3)
C8—C13	1.398 (3)	C20—H20A	0.99
C8—P1	1.813 (2)	C20—H20B	0.99
C9—C10	1.383 (3)	C21—H21A	0.98
C9—H9	0.95	C21—H21B	0.98
C10—C11	1.392 (3)	C21—H21C	0.98
C10—H10	0.95	N1—P1	1.6332 (16)
C11—C12	1.388 (4)	N1—H1	0.88
C11—H11	0.95	O1—P1	1.4910 (14)
C6—C1—C2	118.48 (18)	C8—C13—H13	120.1
C6—C1—C7	122.93 (17)	C19—C14—C15	120.01 (18)
C2—C1—C7	118.59 (17)	C19—C14—P1	126.76 (16)
C3—C2—C1	120.79 (19)	C15—C14—P1	113.20 (15)
C3—C2—H2	119.6	C16—C15—C14	121.0 (2)
C1—C2—H2	119.6	C16—C15—H15	119.5
C4—C3—C2	120.18 (19)	C14—C15—H15	119.5
C4—C3—H3	119.9	C17—C16—C15	119.0 (2)
C2—C3—H3	119.9	C17—C16—H16	120.5
C5—C4—C3	119.48 (18)	C15—C16—H16	120.5
C5—C4—H4	120.3	C18—C17—C16	120.71 (19)
C3—C4—H4	120.3	C18—C17—H17	119.6
C4—C5—C6	120.29 (19)	C16—C17—H17	119.6
C4—C5—H5	119.9	C17—C18—C19	121.8 (2)
C6—C5—H5	119.9	C17—C18—H18	119.1
C1—C6—C5	120.77 (18)	C19—C18—H18	119.1
C1—C6—H6	119.6	C18—C19—C14	117.48 (19)
C5—C6—H6	119.6	C18—C19—C20	120.43 (19)
N1—C7—C1	112.92 (16)	C14—C19—C20	122.08 (18)
N1—C7—H7A	109	C19—C20—C21	116.47 (17)
C1—C7—H7A	109	C19—C20—H20A	108.2
N1—C7—H7B	109	C21—C20—H20A	108.2
C1—C7—H7B	109	C19—C20—H20B	108.2
H7A—C7—H7B	107.8	C21—C20—H20B	108.2
C9—C8—C13	119.37 (19)	H20A—C20—H20B	107.3
C9—C8—P1	122.39 (15)	C20—C21—H21A	109.5
C13—C8—P1	118.21 (16)	C20—C21—H21B	109.5
C10—C9—C8	120.60 (19)	H21A—C21—H21B	109.5
C10—C9—H9	119.7	C20—C21—H21C	109.5
C8—C9—H9	119.7	H21A—C21—H21C	109.5
C9—C10—C11	119.8 (2)	H21B—C21—H21C	109.5
C9—C10—H10	120.1	C7—N1—P1	118.96 (13)
C11—C10—H10	120.1	C7—N1—H1	120.5
C12—C11—C10	119.7 (2)	P1—N1—H1	120.5
C12—C11—H11	120.1	O1—P1—N1	116.67 (8)
C10—C11—H11	120.1	O1—P1—C8	109.12 (8)
C13—C12—C11	120.7 (2)	N1—P1—C8	105.70 (9)
C13—C12—H12	119.6	O1—P1—C14	108.77 (9)
C11—C12—H12	119.6	N1—P1—C14	106.44 (9)
C12—C13—C8	119.8 (2)	C8—P1—C14	110.01 (9)
C12—C13—H13	120.1
C6—C1—C2—C3	0.8 (3)	C17—C18—C19—C20	178.74 (19)
C7—C1—C2—C3	−179.37 (19)	C15—C14—C19—C18	0.1 (3)
C1—C2—C3—C4	−0.2 (3)	P1—C14—C19—C18	−177.67 (15)
C2—C3—C4—C5	−0.5 (3)	C15—C14—C19—C20	−178.96 (19)
C3—C4—C5—C6	0.6 (3)	P1—C14—C19—C20	3.2 (3)
C2—C1—C6—C5	−0.7 (3)	C18—C19—C20—C21	5.3 (3)
C7—C1—C6—C5	179.48 (19)	C14—C19—C20—C21	−175.67 (19)
C4—C5—C6—C1	0.0 (3)	C1—C7—N1—P1	−158.63 (13)
C6—C1—C7—N1	5.2 (3)	C7—N1—P1—O1	−44.63 (17)
C2—C1—C7—N1	−174.62 (17)	C7—N1—P1—C8	76.83 (16)
C13—C8—C9—C10	0.1 (3)	C7—N1—P1—C14	−166.21 (15)
P1—C8—C9—C10	−177.86 (15)	C9—C8—P1—O1	137.49 (16)
C8—C9—C10—C11	−0.2 (3)	C13—C8—P1—O1	−40.47 (17)
C9—C10—C11—C12	0.4 (3)	C9—C8—P1—N1	11.27 (18)
C10—C11—C12—C13	−0.5 (3)	C13—C8—P1—N1	−166.69 (15)
C11—C12—C13—C8	0.4 (3)	C9—C8—P1—C14	−103.26 (17)
C9—C8—C13—C12	−0.2 (3)	C13—C8—P1—C14	78.79 (17)
P1—C8—C13—C12	177.84 (16)	C19—C14—P1—O1	−176.35 (17)
C19—C14—C15—C16	0.5 (3)	C15—C14—P1—O1	5.72 (18)
P1—C14—C15—C16	178.53 (17)	C19—C14—P1—N1	−49.9 (2)
C14—C15—C16—C17	−0.8 (3)	C15—C14—P1—N1	132.20 (15)
C15—C16—C17—C18	0.6 (3)	C19—C14—P1—C8	64.2 (2)
C16—C17—C18—C19	0.0 (3)	C15—C14—P1—C8	−113.75 (16)
C17—C18—C19—C14	−0.4 (3)

Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.09	2.742 (2)	131
C18—H18···Cg2ii	0.95	2.98	3.756 (2)	139
C21—H21C···Cg3ii	0.98	2.83	3.636 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.09	2.742 (2)	131
C18—H18⋯Cg2ii	0.95	2.98	3.756 (2)	139
C21—H21C⋯Cg3ii	0.98	2.83	3.636 (3)	140

Symmetry codes: (i) ; (ii) .