N-Benzyl-P-(2-ethyl­phen­yl)-P-phenyl­phosphinic amide

Kinfe, H.H.; Hamese, A.; Hughes, T.; Omondi, B.

doi:10.1107/S1600536811049014

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3392

https://doi.org/10.1107/S1600536811049014

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N-Benzyl-P-(2-ethylphenyl)-P-phenylphosphinic amide

Henok H. Kinfe,^a ^* Augustine Hamese,^a Tanya Hughes ^a and Bernard Omondi ^b ^*

^aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524 Auckland Park, Johannesburg 2006, South Africa, and ^bSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: hhkinfe@uj.ac.za, owaga@ukzn.ac.za

(Received 10 November 2011; accepted 17 November 2011; online 23 November 2011)

In the crystal structure of the title compound, C₂₁H₂₂NOP, the amine H atom is involved in N—H⋯O hydrogen-bonding interactions, resulting in chains along the c axis. The crystal lattice is consolidated by weak intermolecular C—H⋯π interactions.

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_r = 335.37
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.118
S = 1.05
2946 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.57 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049014/hg5139sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049014/hg5139Isup2.hkl

checkCIF report

Comment top

Phosphinamides are important functional groups in organic synthesis. They have been employed as amine protecting groups and as substrates for imine activation (Wuts et al., 2006). Besides functioning as protective groups, phosphinamides are also used as catalysts for enantioselective reduction of ketones as building blocks for the synthesis of peptidomimetics via phosphinamide-directed benzylic lithiation (Burgos et al., 2008) and also as chiral ligands (Popovici et al., 2010). Herein, we have synthesized a racemic mixture of a chiral phosphinamide and report its crystal structure.

The asymmetric unit of (I), (Fig. 1) contains one molecule. The phosphorus is in a tetrahedral environment as in other phosphine oxides. The P==O, P–N and P–C bond distances are comparable to similar compounds in literature (Priya et al., 2005; Fei et al., 2004; Gaw et al., 1999). In the crystal of (I), O atom is involved in N–H···O==P hydrogen bonding interaction (Table 1), thus resulting in chains that run in the crystallographic c direction. The crystal lattice is consolidated by a pair of weak C–H···π intermolecular interactions [C18···Cg = 3.756 (2) Å, <C18–H18···Cg = 139 ° C21···Cg = 3.636 (3) Å, <C21–H21c···Cg = 140 °] (Fig. 2).

Related literature top

For the uses of phosphinamides, see: Wuts et al., (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 top

To a solution of 1-bromo-2-ethylbenzene (1 ml, 7.3 mmol) in dry THF (10 ml) were added Mg (263 mg, 11 mmol) and a catalytic amount of iodine crystals. The resulting mixture was refluxed overnight under nitrogen atmosphere. The resulting Grignard reagent was added drop wise to a solution of PhPCl₂ (1.2 ml, 8.31 mmol) in THF (10 ml) at -70 °C and stirred for 3 h followed by addition of benzylamine (1.8 ml, 16.62 mmol). After stirring the reaction mixture for 4 h at -70 °C under nitrogen atmosphere, 30% aq hydrogen peroxide (5 ml) was added at 0 °C and stirred at this temperature for an additional 1 hr. The reaction mixture was then allowed to warm up to room temperature, ethylacetate (20 ml) was added and the resulting solution was washed with water (3 x 20 ml). The ethylacetate layer was dried over Na₂SO₄, filtered, and evaporated. The residue product was purified by crystallization from a 1:2 mixture of DCM and hexane to afford the title compound in 55% yield as white crystals; mp 104–107 °C;

¹H NMR (CDCl₃, 400 MHz): δ 7.90–7.71 (m, 3H), 7.49–7.13 (m, 11H), 4.92–4.70 (m, NH peak), 4.22 (d, J = 8.0 Hz, 2H), 3.06 (q, J = 7.4 and 15.0 Hz, 2H), 1.10 (t, J = 7.6 Hz, 3H); ¹³C NMR (CDCl₃, 75 MHz): δ 149.2, 149.0, 139.7, 139.6, 133.1, 132.9, 132.2, 133.0, 131.8, 131.7, 130.2, 130.0, 128.7, 128.6, 128.4, 127.8, 127.3, 125.4, 125.3, 44.8, 27.1, 15.5; ³¹P NMR (CDCl₃, 400 MHz): δ 27.03.

Structure description top

Computing details top

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).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of the crystal of (I) showing chains of N—H···O intermolecular interactions as viewed down the crystallographic c direction.

N-Benzyl-P-(2-ethylphenyl)-P-phenylphosphinic amide top

Crystal data top

C₂₁H₂₂NOP	F(000) = 712
M_r = 335.37	D_x = 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

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	2772 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 66.2°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→14
T_min = 0.549, T_max = 0.972	k = −18→18
13806 measured reflections	l = −9→10
2946 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0573P)² + 1.6926P] where P = (F_o² + 2F_c²)/3
2946 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₂₁H₂₂NOP	V = 1761.73 (7) Å³
M_r = 335.37	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.9259 (3) Å	µ = 1.42 mm⁻¹
b = 15.7098 (3) Å	T = 100 K
c = 9.1007 (2) Å	0.48 × 0.08 × 0.02 mm
β = 107.578 (1)°

Data collection top

Bruker X8 APEXII 4K KappaCCD diffractometer	2946 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2772 reflections with I > 2σ(I)
T_min = 0.549, T_max = 0.972	R_int = 0.034
13806 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.57 e Å⁻³
2946 reflections	Δρ_min = −0.57 e Å⁻³
218 parameters

Special details top

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:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂NOP
M_r	335.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.9259 (3), 15.7098 (3), 9.1007 (2)
β (°)	107.578 (1)
V (Å³)	1761.73 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.42
Crystal size (mm)	0.48 × 0.08 × 0.02

Data collection
Diffractometer	Bruker X8 APEXII 4K KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.549, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	13806, 2946, 2772
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.118, 1.05
No. of reflections	2946
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.57

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, −y, −z+1.

Acknowledgements

We thank NRF, THRIP and University of Johannesburg for financial support.

References

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