O-Phenyl (cyclo­hexyl­amido)(p-tolyl­amido)­phosphinate

Sabbaghi, F.; Pourayoubi, M.; Karimi Ahmadabad, F.; Parvez, M.

doi:10.1107/S1600536811018502

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1502

doi:10.1107/S1600536811018502

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O-Phenyl (cyclohexylamido)(p-tolylamido)phosphinate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi,^b Fatemeh Karimi Ahmadabad ^b and Masood Parvez ^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 ^cDepartment of Chemistry, University of Calgary, 2500 University Drive, N.W., Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 8 May 2011; accepted 16 May 2011; online 25 May 2011)

In the title molecule, C₁₉H₂₅N₂O₂P, the P atom is bonded in a distorted tetrahedral 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 R₂²(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_r = 344.38
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.124
S = 1.06
4172 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811018502/lh5250Isup3.cml

checkCIF report

Comment top

The structure determination of title compound was performed as a part of a project in our laboratory on the synthesis of new mixed-amido phosphinates having a P(O)(O)(N')(N") skeleton (Pourayoubi et al., 2007).

The P═O, P—O and P—N bond lengths are standard for this type of compound (Pourayoubi et al., 2007). The P atom has a distorted tetrahedral configuration (Fig. 1) with the bond angles in the range of 98.55 (10)° [O2–P1–N1] to 119.80 (10)° [O1–P1–N1].

The phosphoryl group respectively adopts a syn orientation with respect to the N–H unit of p-tolylamido moiety and a gauche position relative to that of cyclohexylamido substituent.

In the crystal structure, the molecules are linked by two intermolecular N—H···OP hydrogen bonds (Table 1) into chains in the direction of the b axis in which the O atom of the P═O group acts as a double H-acceptor (Steiner, 2002) (Fig. 2). From this arrangement R₂²(8) rings are formed (Bernstein et al., 1995).

Related literature top

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 top

To a solution of (C₆H₅O)(4-CH₃C₆H₄NH)P(O)Cl in chloroform, a solution of cyclohexylamine (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 CH₃CN/CHCl₃ after slow evaporation at room temperature.

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level. The disorder is not shown.
	Fig. 2. Part of the crystal structure of the title compound with hydrogen bonding shown as dotted lines (the C—H hydrogen atoms are omitted for clarity).

N-[(Cyclohexylamino)(phenoxy)phosphoryl]-4-methylaniline top

Crystal data top

C₁₉H₂₅N₂O₂P	F(000) = 736
M_r = 344.38	D_x = 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

Data collection top

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

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)] = 0.056	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(F_o²) + (0.0234P)² + 2.302P] where P = (F_o² + 2F_c²)/3
4172 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₉H₂₅N₂O₂P	V = 1832.17 (10) Å³
M_r = 344.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.5575 (4) Å	µ = 0.16 mm⁻¹
b = 7.7006 (3) Å	T = 173 K
c = 16.1717 (4) Å	0.16 × 0.14 × 0.10 mm
β = 108.9709 (17)°

Data collection top

Nonius KappaCCD diffractometer	4172 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3069 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.984	R_int = 0.070
13695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.27 e Å⁻³
4172 reflections	Δρ_min = −0.38 e Å⁻³
223 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.

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅N₂O₂P
M_r	344.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	15.5575 (4), 7.7006 (3), 16.1717 (4)
β (°)	108.9709 (17)
V (Å³)	1832.17 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.974, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	13695, 4172, 3069
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.124, 1.06
No. of reflections	4172
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.38

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2.

Acknowledgements

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

References

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