Diphenyl (o-tolyl­amido)­phospho­nate

Sabbaghi, F.; Pourayoubi, M.; Zargaran, P.

doi:10.1107/S1600536811013924

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1170

doi:10.1107/S1600536811013924

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Diphenyl (o-tolylamido)phosphonate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi ^b and Poorya Zargaran ^b

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran, and ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 31 March 2011; accepted 13 April 2011; online 16 April 2011)

The asymmetric unit of the title compound, C₁₉H₁₈NO₃P, contains two independent molecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form two independent centrosymmetric dimers.

Related literature

For a related structure, see: Pourayoubi et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₈NO₃P
M_r = 339.31
Triclinic, $[P \overline 1]$
a = 10.2986 (13) Å
b = 10.3540 (12) Å
c = 17.993 (2) Å
α = 86.650 (2)°
β = 84.036 (2)°
γ = 62.429 (2)°
V = 1691.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 120 K
0.50 × 0.40 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.918, T_max = 0.956
17593 measured reflections
8135 independent reflections
6772 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.00
8135 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.85 (2)	2.09 (2)	2.903 (1)	162 (1)
N1′—H1′N⋯O1′ⁱⁱ	0.86 (2)	2.02 (2)	2.867 (1)	167 (1)
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013924/lh5229sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013924/lh5229Isup2.hkl

checkCIF report

Comment top

In previous work, the structure of diphenyl (p-tolylamido)phosphate was reported (Pourayoubi et al., 2010). Here, we report on the synthesis and crystal structure of title compound.

The asymmetric unit (Fig. 1) consists of two independent molecules. The P═O, P—O and P—N bond lengths are standard for amidophosphoric acid ester compounds (Pourayoubi et al., 2010). The P atoms of two independent molecules are in slightly distorted tetrahedral environments.

In each molecule, the phosphoryl group and the N-H unit are in a syn orientation with respect to each other and in the crystal, pairs of intermolecular N—H···O(P) hydrogen bonds (Table 1) form two independent centrosymmetric dimers (Fig. 2).

Related literature top

For a related structure, see: Pourayoubi et al. (2010).

Experimental top

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of ortho-toluidine (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. Colorless plates were obtained by slow evaporation of a methanol solution of the title compound at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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).

Figures top

	Fig. 1. The asymmetric unit of title compound with ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dotted lines. Only H atoms involved in hydrogen bonds are shown.

Diphenyl (o-tolylamido)phosphonate top

Crystal data top

C₁₉H₁₈NO₃P	Z = 4
M_r = 339.31	F(000) = 712
Triclinic, P1	D_x = 1.332 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2986 (13) Å	Cell parameters from 512 reflections
b = 10.3540 (12) Å	θ = 4.5–56.0°
c = 17.993 (2) Å	µ = 0.18 mm⁻¹
α = 86.650 (2)°	T = 120 K
β = 84.036 (2)°	Plate, colorless
γ = 62.429 (2)°	0.50 × 0.40 × 0.25 mm
V = 1691.4 (4) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	8135 independent reflections
Radiation source: fine-focus sealed tube	6772 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
T_min = 0.918, T_max = 0.956	k = −13→13
17593 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: mixed
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0458P)² + 0.9439P] where P = (F_o² + 2F_c²)/3
8135 reflections	(Δ/σ)_max = 0.001
441 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₈NO₃P	γ = 62.429 (2)°
M_r = 339.31	V = 1691.4 (4) Å³
Triclinic, P1	Z = 4
a = 10.2986 (13) Å	Mo Kα radiation
b = 10.3540 (12) Å	µ = 0.18 mm⁻¹
c = 17.993 (2) Å	T = 120 K
α = 86.650 (2)°	0.50 × 0.40 × 0.25 mm
β = 84.036 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	8135 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	6772 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.956	R_int = 0.018
17593 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.31 e Å⁻³
8135 reflections	Δρ_min = −0.34 e Å⁻³
441 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
P1	0.19581 (4)	0.01563 (4)	0.03088 (2)	0.02376 (9)
P1'	0.70287 (4)	0.52900 (4)	0.47655 (2)	0.02586 (9)
O1	0.04093 (11)	0.08523 (11)	0.05977 (6)	0.0281 (2)
O1'	0.55749 (12)	0.60327 (12)	0.44825 (6)	0.0307 (2)
N1	0.23929 (14)	−0.13554 (13)	−0.01151 (7)	0.0257 (2)
H1N	0.161 (2)	−0.138 (2)	−0.0202 (12)	0.044 (6)*
N1'	0.72932 (14)	0.37818 (13)	0.52085 (7)	0.0273 (3)
H1'N	0.649 (2)	0.371 (2)	0.5267 (11)	0.035 (5)*
C1'	0.85909 (16)	0.27308 (15)	0.55182 (8)	0.0250 (3)
C1	0.37739 (16)	−0.23456 (15)	−0.04656 (8)	0.0252 (3)
O2	0.31273 (11)	−0.01688 (11)	0.08885 (6)	0.0275 (2)
O2'	0.74025 (12)	0.62773 (11)	0.52562 (6)	0.0295 (2)
C2	0.49794 (17)	−0.20592 (16)	−0.05467 (9)	0.0295 (3)
H2A	0.4883	−0.1171	−0.0368	0.035*
C2'	0.97362 (17)	0.30462 (16)	0.56286 (9)	0.0289 (3)
H2'A	0.9657	0.3979	0.5494	0.035*
O3	0.24525 (11)	0.11823 (11)	−0.02046 (6)	0.0272 (2)
O3'	0.83944 (11)	0.49332 (11)	0.41738 (6)	0.0288 (2)
C3'	1.09885 (17)	0.20008 (17)	0.59340 (9)	0.0306 (3)
H3'A	1.1765	0.2220	0.6006	0.037*
C3	0.63124 (18)	−0.30587 (18)	−0.08845 (9)	0.0339 (3)
H3A	0.7126	−0.2853	−0.0938	0.041*
C4'	1.11138 (18)	0.06399 (17)	0.61338 (9)	0.0316 (3)
H4'A	1.1968	−0.0073	0.6347	0.038*
C4	0.64678 (18)	−0.43601 (18)	−0.11448 (10)	0.0356 (3)
H4A	0.7383	−0.5049	−0.1377	0.043*
C5'	0.99799 (18)	0.03281 (17)	0.60188 (9)	0.0308 (3)
H5'A	1.0073	−0.0610	0.6153	0.037*
C5	0.52688 (18)	−0.46445 (17)	−0.10627 (9)	0.0333 (3)
H5A	0.5381	−0.5541	−0.1239	0.040*
C6'	0.87077 (16)	0.13484 (16)	0.57128 (8)	0.0262 (3)
C6	0.39121 (17)	−0.36614 (16)	−0.07314 (8)	0.0277 (3)
C7'	0.75118 (18)	0.09580 (17)	0.55958 (10)	0.0328 (3)
H7'A	0.7800	−0.0047	0.5765	0.049*
H7'B	0.7353	0.1048	0.5064	0.049*
H7'C	0.6601	0.1618	0.5883	0.049*
C7	0.26449 (18)	−0.40159 (17)	−0.06492 (10)	0.0341 (3)
H7A	0.2955	−0.4972	−0.0866	0.051*
H7B	0.1829	−0.3273	−0.0910	0.051*
H7C	0.2325	−0.4034	−0.0118	0.051*
C8	0.34238 (16)	−0.11692 (15)	0.14859 (8)	0.0252 (3)
C8'	0.64352 (16)	0.71344 (16)	0.58442 (8)	0.0278 (3)
C9	0.48097 (17)	−0.16872 (18)	0.17359 (9)	0.0326 (3)
H9A	0.5504	−0.1406	0.1492	0.039*
C9'	0.6185 (2)	0.6498 (2)	0.65008 (10)	0.0398 (4)
H9'A	0.6587	0.5469	0.6547	0.048*
C10	0.51614 (19)	−0.26239 (18)	0.23491 (10)	0.0373 (4)
H10A	0.6106	−0.2987	0.2527	0.045*
C10'	0.5339 (2)	0.7386 (3)	0.70923 (11)	0.0525 (5)
H10B	0.5147	0.6966	0.7547	0.063*
C11	0.41501 (19)	−0.30358 (17)	0.27055 (9)	0.0340 (3)
H11A	0.4395	−0.3669	0.3129	0.041*
C11'	0.4774 (2)	0.8877 (3)	0.70230 (11)	0.0527 (5)
H11B	0.4206	0.9479	0.7433	0.063*
C12	0.27790 (18)	−0.25192 (17)	0.24404 (9)	0.0313 (3)
H12A	0.2087	−0.2807	0.2682	0.038*
C12'	0.5030 (2)	0.9502 (2)	0.63599 (12)	0.0464 (5)
H12B	0.4633	1.0531	0.6314	0.056*
C13	0.24039 (16)	−0.15821 (16)	0.18236 (8)	0.0277 (3)
H13A	0.1467	−0.1234	0.1639	0.033*
C13'	0.58688 (17)	0.86229 (17)	0.57605 (10)	0.0324 (3)
H13B	0.6048	0.9040	0.5302	0.039*
C14'	0.88130 (16)	0.39496 (15)	0.35856 (8)	0.0272 (3)
C14	0.16958 (16)	0.19573 (16)	−0.08173 (8)	0.0281 (3)
C15	0.15880 (19)	0.12386 (19)	−0.14134 (9)	0.0349 (3)
H15A	0.1947	0.0212	−0.1398	0.042*
C15'	1.02970 (17)	0.32833 (17)	0.33465 (9)	0.0329 (3)
H15B	1.0973	0.3447	0.3598	0.039*
C16'	1.07788 (19)	0.23765 (19)	0.27364 (10)	0.0392 (4)
H16A	1.1793	0.1920	0.2566	0.047*
C16	0.0943 (2)	0.2051 (2)	−0.20348 (10)	0.0436 (4)
H16B	0.0849	0.1576	−0.2447	0.052*
C17'	0.9801 (2)	0.21280 (18)	0.23727 (10)	0.0394 (4)
H17A	1.0138	0.1511	0.1950	0.047*
C17	0.0437 (2)	0.3538 (2)	−0.20598 (11)	0.0478 (5)
H17B	0.0012	0.4082	−0.2491	0.057*
C18'	0.8327 (2)	0.27838 (18)	0.26281 (10)	0.0383 (4)
H18A	0.7656	0.2602	0.2382	0.046*
C18	0.0550 (2)	0.4240 (2)	−0.14562 (12)	0.0475 (5)
H18B	0.0197	0.5266	−0.1474	0.057*
C19'	0.78125 (18)	0.37031 (17)	0.32386 (9)	0.0330 (3)
H19A	0.6800	0.4151	0.3413	0.040*
C19	0.11776 (18)	0.34487 (18)	−0.08233 (10)	0.0364 (4)
H19B	0.1248	0.3925	−0.0405	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.02526 (18)	0.02339 (17)	0.02499 (18)	−0.01273 (15)	−0.00391 (14)	−0.00136 (13)
P1'	0.02571 (19)	0.02501 (18)	0.0303 (2)	−0.01476 (15)	−0.00277 (14)	0.00181 (14)
O1	0.0261 (5)	0.0289 (5)	0.0288 (5)	−0.0119 (4)	−0.0020 (4)	−0.0045 (4)
O1'	0.0272 (5)	0.0304 (5)	0.0366 (6)	−0.0152 (4)	−0.0050 (4)	0.0060 (4)
N1	0.0243 (6)	0.0249 (6)	0.0312 (6)	−0.0135 (5)	−0.0037 (5)	−0.0041 (5)
N1'	0.0264 (6)	0.0258 (6)	0.0349 (7)	−0.0165 (5)	−0.0044 (5)	0.0032 (5)
C1'	0.0265 (7)	0.0258 (7)	0.0235 (7)	−0.0128 (6)	−0.0009 (5)	−0.0005 (5)
C1	0.0261 (7)	0.0234 (7)	0.0249 (7)	−0.0099 (6)	−0.0046 (5)	0.0004 (5)
O2	0.0302 (5)	0.0293 (5)	0.0279 (5)	−0.0173 (4)	−0.0068 (4)	0.0020 (4)
O2'	0.0295 (5)	0.0261 (5)	0.0368 (6)	−0.0164 (4)	−0.0002 (4)	−0.0032 (4)
C2	0.0282 (7)	0.0278 (7)	0.0342 (8)	−0.0137 (6)	−0.0038 (6)	−0.0037 (6)
C2'	0.0318 (8)	0.0283 (7)	0.0313 (7)	−0.0177 (6)	−0.0043 (6)	0.0020 (6)
O3	0.0304 (5)	0.0257 (5)	0.0291 (5)	−0.0155 (4)	−0.0059 (4)	0.0020 (4)
O3'	0.0288 (5)	0.0296 (5)	0.0326 (5)	−0.0174 (4)	−0.0012 (4)	−0.0008 (4)
C3'	0.0304 (8)	0.0355 (8)	0.0293 (7)	−0.0178 (7)	−0.0047 (6)	0.0013 (6)
C3	0.0288 (8)	0.0376 (8)	0.0367 (8)	−0.0159 (7)	−0.0041 (6)	−0.0044 (7)
C4'	0.0329 (8)	0.0305 (7)	0.0294 (8)	−0.0126 (6)	−0.0050 (6)	0.0024 (6)
C4	0.0294 (8)	0.0339 (8)	0.0366 (8)	−0.0080 (7)	−0.0035 (6)	−0.0070 (7)
C5'	0.0378 (8)	0.0262 (7)	0.0289 (7)	−0.0155 (6)	−0.0017 (6)	0.0024 (6)
C5	0.0367 (8)	0.0260 (7)	0.0341 (8)	−0.0108 (6)	−0.0058 (6)	−0.0045 (6)
C6'	0.0305 (7)	0.0263 (7)	0.0247 (7)	−0.0160 (6)	0.0019 (6)	−0.0029 (5)
C6	0.0330 (8)	0.0244 (7)	0.0279 (7)	−0.0142 (6)	−0.0077 (6)	0.0012 (5)
C7'	0.0356 (8)	0.0286 (7)	0.0403 (9)	−0.0199 (7)	−0.0019 (7)	−0.0014 (6)
C7	0.0385 (9)	0.0277 (7)	0.0416 (9)	−0.0191 (7)	−0.0054 (7)	−0.0035 (6)
C8	0.0272 (7)	0.0227 (6)	0.0241 (7)	−0.0094 (6)	−0.0041 (5)	−0.0029 (5)
C8'	0.0255 (7)	0.0312 (7)	0.0302 (7)	−0.0156 (6)	−0.0046 (6)	−0.0007 (6)
C9	0.0283 (8)	0.0369 (8)	0.0343 (8)	−0.0158 (7)	−0.0053 (6)	−0.0014 (6)
C9'	0.0398 (9)	0.0477 (10)	0.0369 (9)	−0.0247 (8)	−0.0066 (7)	0.0098 (7)
C10	0.0328 (8)	0.0378 (9)	0.0394 (9)	−0.0126 (7)	−0.0139 (7)	0.0009 (7)
C10'	0.0483 (11)	0.0884 (16)	0.0309 (9)	−0.0407 (11)	−0.0025 (8)	0.0039 (9)
C11	0.0390 (9)	0.0298 (8)	0.0285 (8)	−0.0110 (7)	−0.0087 (6)	0.0019 (6)
C11'	0.0371 (10)	0.0828 (16)	0.0437 (11)	−0.0315 (10)	0.0076 (8)	−0.0273 (10)
C12	0.0336 (8)	0.0288 (7)	0.0294 (8)	−0.0129 (6)	−0.0008 (6)	−0.0008 (6)
C12'	0.0335 (9)	0.0430 (10)	0.0637 (12)	−0.0175 (8)	0.0009 (8)	−0.0190 (9)
C13	0.0243 (7)	0.0279 (7)	0.0289 (7)	−0.0101 (6)	−0.0028 (6)	−0.0010 (6)
C13'	0.0295 (8)	0.0309 (8)	0.0395 (9)	−0.0160 (6)	−0.0042 (6)	0.0004 (6)
C14'	0.0297 (7)	0.0232 (7)	0.0275 (7)	−0.0115 (6)	−0.0031 (6)	0.0034 (5)
C14	0.0252 (7)	0.0305 (7)	0.0294 (7)	−0.0141 (6)	−0.0017 (6)	0.0036 (6)
C15	0.0378 (9)	0.0385 (8)	0.0281 (8)	−0.0175 (7)	−0.0025 (6)	−0.0001 (6)
C15'	0.0280 (8)	0.0335 (8)	0.0365 (8)	−0.0143 (6)	−0.0028 (6)	0.0046 (6)
C16'	0.0334 (8)	0.0348 (8)	0.0404 (9)	−0.0096 (7)	0.0033 (7)	0.0022 (7)
C16	0.0443 (10)	0.0618 (12)	0.0293 (8)	−0.0286 (9)	−0.0056 (7)	0.0070 (8)
C17'	0.0479 (10)	0.0297 (8)	0.0316 (8)	−0.0108 (7)	−0.0016 (7)	0.0001 (6)
C17	0.0385 (10)	0.0624 (12)	0.0470 (11)	−0.0282 (9)	−0.0136 (8)	0.0266 (9)
C18'	0.0424 (9)	0.0358 (8)	0.0364 (9)	−0.0163 (7)	−0.0102 (7)	−0.0008 (7)
C18	0.0407 (10)	0.0379 (9)	0.0665 (13)	−0.0209 (8)	−0.0141 (9)	0.0212 (9)
C19'	0.0279 (8)	0.0326 (8)	0.0366 (8)	−0.0117 (6)	−0.0063 (6)	0.0004 (6)
C19	0.0340 (8)	0.0306 (8)	0.0480 (10)	−0.0179 (7)	−0.0058 (7)	0.0056 (7)

Geometric parameters (Å, º) top

P1—O1	1.4633 (11)	C8—C13	1.381 (2)
P1—O2	1.5799 (11)	C8—C9	1.387 (2)
P1—O3	1.5904 (11)	C8'—C13'	1.377 (2)
P1—N1	1.6284 (12)	C8'—C9'	1.378 (2)
P1'—O1'	1.4626 (11)	C9—C10	1.386 (2)
P1'—O3'	1.5818 (11)	C9—H9A	0.9500
P1'—O2'	1.5852 (11)	C9'—C10'	1.385 (3)
P1'—N1'	1.6290 (13)	C9'—H9'A	0.9500
N1—C1	1.4181 (19)	C10—C11	1.385 (2)
N1—H1N	0.85 (2)	C10—H10A	0.9500
N1'—C1'	1.4207 (19)	C10'—C11'	1.377 (3)
N1'—H1'N	0.86 (2)	C10'—H10B	0.9500
C1'—C2'	1.396 (2)	C11—C12	1.385 (2)
C1'—C6'	1.4060 (19)	C11—H11A	0.9500
C1—C2	1.396 (2)	C11'—C12'	1.384 (3)
C1—C6	1.4097 (19)	C11'—H11B	0.9500
O2—C8	1.4024 (17)	C12—C13	1.392 (2)
O2'—C8'	1.4041 (18)	C12—H12A	0.9500
C2—C3	1.382 (2)	C12'—C13'	1.390 (2)
C2—H2A	0.9500	C12'—H12B	0.9500
C2'—C3'	1.386 (2)	C13—H13A	0.9500
C2'—H2'A	0.9500	C13'—H13B	0.9500
O3—C14	1.4011 (18)	C14'—C19'	1.383 (2)
O3'—C14'	1.4028 (18)	C14'—C15'	1.385 (2)
C3'—C4'	1.383 (2)	C14—C19	1.381 (2)
C3'—H3'A	0.9500	C14—C15	1.382 (2)
C3—C4	1.385 (2)	C15—C16	1.388 (2)
C3—H3A	0.9500	C15—H15A	0.9500
C4'—C5'	1.385 (2)	C15'—C16'	1.382 (2)
C4'—H4'A	0.9500	C15'—H15B	0.9500
C4—C5	1.388 (2)	C16'—C17'	1.380 (3)
C4—H4A	0.9500	C16'—H16A	0.9500
C5'—C6'	1.392 (2)	C16—C17	1.378 (3)
C5'—H5'A	0.9500	C16—H16B	0.9500
C5—C6	1.387 (2)	C17'—C18'	1.384 (3)
C5—H5A	0.9500	C17'—H17A	0.9500
C6'—C7'	1.500 (2)	C17—C18	1.385 (3)
C6—C7	1.502 (2)	C17—H17B	0.9500
C7'—H7'A	0.9800	C18'—C19'	1.388 (2)
C7'—H7'B	0.9800	C18'—H18A	0.9500
C7'—H7'C	0.9800	C18—C19	1.393 (3)
C7—H7A	0.9800	C18—H18B	0.9500
C7—H7B	0.9800	C19'—H19A	0.9500
C7—H7C	0.9800	C19—H19B	0.9500

O1—P1—O2	116.87 (6)	C13—C8—O2	123.06 (13)
O1—P1—O3	114.56 (6)	C9—C8—O2	115.18 (13)
O2—P1—O3	93.94 (5)	C13'—C8'—C9'	121.93 (16)
O1—P1—N1	111.23 (6)	C13'—C8'—O2'	117.01 (14)
O2—P1—N1	108.09 (6)	C9'—C8'—O2'	120.77 (14)
O3—P1—N1	110.93 (6)	C10—C9—C8	118.70 (15)
O1'—P1'—O3'	116.62 (6)	C10—C9—H9A	120.7
O1'—P1'—O2'	114.45 (6)	C8—C9—H9A	120.7
O3'—P1'—O2'	93.95 (6)	C8'—C9'—C10'	118.82 (18)
O1'—P1'—N1'	111.98 (7)	C8'—C9'—H9'A	120.6
O3'—P1'—N1'	107.75 (6)	C10'—C9'—H9'A	120.6
O2'—P1'—N1'	110.71 (6)	C11—C10—C9	120.72 (15)
C1—N1—P1	128.61 (10)	C11—C10—H10A	119.6
C1—N1—H1N	120.6 (14)	C9—C10—H10A	119.6
P1—N1—H1N	109.1 (14)	C11'—C10'—C9'	120.18 (18)
C1'—N1'—P1'	128.14 (10)	C11'—C10'—H10B	119.9
C1'—N1'—H1'N	121.4 (13)	C9'—C10'—H10B	119.9
P1'—N1'—H1'N	110.3 (13)	C10—C11—C12	119.58 (15)
C2'—C1'—C6'	120.07 (13)	C10—C11—H11A	120.2
C2'—C1'—N1'	121.39 (13)	C12—C11—H11A	120.2
C6'—C1'—N1'	118.54 (13)	C10'—C11'—C12'	120.42 (18)
C2—C1—C6	119.91 (14)	C10'—C11'—H11B	119.8
C2—C1—N1	122.19 (13)	C12'—C11'—H11B	119.8
C6—C1—N1	117.90 (13)	C11—C12—C13	120.69 (15)
C8—O2—P1	125.79 (9)	C11—C12—H12A	119.7
C8'—O2'—P1'	122.76 (9)	C13—C12—H12A	119.7
C3—C2—C1	120.49 (14)	C11'—C12'—C13'	119.92 (18)
C3—C2—H2A	119.8	C11'—C12'—H12B	120.0
C1—C2—H2A	119.8	C13'—C12'—H12B	120.0
C3'—C2'—C1'	120.16 (14)	C8—C13—C12	118.57 (14)
C3'—C2'—H2'A	119.9	C8—C13—H13A	120.7
C1'—C2'—H2'A	119.9	C12—C13—H13A	120.7
C14—O3—P1	122.12 (9)	C8'—C13'—C12'	118.72 (17)
C14'—O3'—P1'	124.49 (9)	C8'—C13'—H13B	120.6
C4'—C3'—C2'	120.41 (14)	C12'—C13'—H13B	120.6
C4'—C3'—H3'A	119.8	C19'—C14'—C15'	121.58 (15)
C2'—C3'—H3'A	119.8	C19'—C14'—O3'	122.75 (14)
C2—C3—C4	120.28 (15)	C15'—C14'—O3'	115.60 (13)
C2—C3—H3A	119.9	C19—C14—C15	121.98 (15)
C4—C3—H3A	119.9	C19—C14—O3	116.85 (14)
C3'—C4'—C5'	119.25 (14)	C15—C14—O3	120.95 (14)
C3'—C4'—H4'A	120.4	C14—C15—C16	118.51 (16)
C5'—C4'—H4'A	120.4	C14—C15—H15A	120.7
C3—C4—C5	119.17 (15)	C16—C15—H15A	120.7
C3—C4—H4A	120.4	C16'—C15'—C14'	118.97 (15)
C5—C4—H4A	120.4	C16'—C15'—H15B	120.5
C4'—C5'—C6'	121.97 (14)	C14'—C15'—H15B	120.5
C4'—C5'—H5'A	119.0	C17'—C16'—C15'	120.66 (16)
C6'—C5'—H5'A	119.0	C17'—C16'—H16A	119.7
C6—C5—C4	122.08 (15)	C15'—C16'—H16A	119.7
C6—C5—H5A	119.0	C17—C16—C15	120.67 (18)
C4—C5—H5A	119.0	C17—C16—H16B	119.7
C5'—C6'—C1'	118.13 (13)	C15—C16—H16B	119.7
C5'—C6'—C7'	120.03 (13)	C16'—C17'—C18'	119.49 (16)
C1'—C6'—C7'	121.83 (14)	C16'—C17'—H17A	120.3
C5—C6—C1	118.07 (14)	C18'—C17'—H17A	120.3
C5—C6—C7	120.38 (14)	C16—C17—C18	120.00 (17)
C1—C6—C7	121.54 (14)	C16—C17—H17B	120.0
C6'—C7'—H7'A	109.5	C18—C17—H17B	120.0
C6'—C7'—H7'B	109.5	C17'—C18'—C19'	121.02 (16)
H7'A—C7'—H7'B	109.5	C17'—C18'—H18A	119.5
C6'—C7'—H7'C	109.5	C19'—C18'—H18A	119.5
H7'A—C7'—H7'C	109.5	C17—C18—C19	120.29 (17)
H7'B—C7'—H7'C	109.5	C17—C18—H18B	119.9
C6—C7—H7A	109.5	C19—C18—H18B	119.9
C6—C7—H7B	109.5	C14'—C19'—C18'	118.25 (15)
H7A—C7—H7B	109.5	C14'—C19'—H19A	120.9
C6—C7—H7C	109.5	C18'—C19'—H19A	120.9
H7A—C7—H7C	109.5	C14—C19—C18	118.53 (17)
H7B—C7—H7C	109.5	C14—C19—H19B	120.7
C13—C8—C9	121.73 (14)	C18—C19—H19B	120.7

O1—P1—N1—C1	−179.73 (12)	C2—C1—C6—C7	179.49 (14)
O2—P1—N1—C1	−50.16 (14)	N1—C1—C6—C7	0.0 (2)
O3—P1—N1—C1	51.51 (14)	P1—O2—C8—C13	−25.96 (19)
O1'—P1'—N1'—C1'	175.80 (12)	P1—O2—C8—C9	156.16 (11)
O3'—P1'—N1'—C1'	46.27 (14)	P1'—O2'—C8'—C13'	−114.99 (13)
O2'—P1'—N1'—C1'	−55.17 (14)	P1'—O2'—C8'—C9'	71.06 (17)
P1'—N1'—C1'—C2'	15.3 (2)	C13—C8—C9—C10	−1.1 (2)
P1'—N1'—C1'—C6'	−164.52 (11)	O2—C8—C9—C10	176.79 (13)
P1—N1—C1—C2	−5.7 (2)	C13'—C8'—C9'—C10'	0.0 (3)
P1—N1—C1—C6	173.76 (11)	O2'—C8'—C9'—C10'	173.69 (15)
O1—P1—O2—C8	66.73 (13)	C8—C9—C10—C11	0.0 (2)
O3—P1—O2—C8	−173.14 (11)	C8'—C9'—C10'—C11'	−0.7 (3)
N1—P1—O2—C8	−59.61 (12)	C9—C10—C11—C12	0.8 (2)
O1'—P1'—O2'—C8'	48.83 (13)	C9'—C10'—C11'—C12'	0.9 (3)
O3'—P1'—O2'—C8'	170.49 (11)	C10—C11—C12—C13	−0.5 (2)
N1'—P1'—O2'—C8'	−78.86 (12)	C10'—C11'—C12'—C13'	−0.4 (3)
C6—C1—C2—C3	−0.2 (2)	C9—C8—C13—C12	1.4 (2)
N1—C1—C2—C3	179.30 (14)	O2—C8—C13—C12	−176.37 (13)
C6'—C1'—C2'—C3'	−0.3 (2)	C11—C12—C13—C8	−0.5 (2)
N1'—C1'—C2'—C3'	179.81 (14)	C9'—C8'—C13'—C12'	0.4 (2)
O1—P1—O3—C14	−52.23 (12)	O2'—C8'—C13'—C12'	−173.45 (14)
O2—P1—O3—C14	−174.20 (11)	C11'—C12'—C13'—C8'	−0.2 (3)
N1—P1—O3—C14	74.72 (12)	P1'—O3'—C14'—C19'	31.11 (19)
O1'—P1'—O3'—C14'	−66.01 (12)	P1'—O3'—C14'—C15'	−151.86 (11)
O2'—P1'—O3'—C14'	174.08 (11)	P1—O3—C14—C19	123.66 (13)
N1'—P1'—O3'—C14'	60.86 (12)	P1—O3—C14—C15	−61.57 (18)
C1'—C2'—C3'—C4'	−0.2 (2)	C19—C14—C15—C16	0.3 (2)
C1—C2—C3—C4	−0.2 (2)	O3—C14—C15—C16	−174.23 (14)
C2'—C3'—C4'—C5'	0.6 (2)	C19'—C14'—C15'—C16'	1.4 (2)
C2—C3—C4—C5	0.1 (3)	O3'—C14'—C15'—C16'	−175.64 (14)
C3'—C4'—C5'—C6'	−0.5 (2)	C14'—C15'—C16'—C17'	−0.5 (2)
C3—C4—C5—C6	0.4 (3)	C14—C15—C16—C17	0.8 (3)
C4'—C5'—C6'—C1'	0.0 (2)	C15'—C16'—C17'—C18'	−0.7 (3)
C4'—C5'—C6'—C7'	179.74 (15)	C15—C16—C17—C18	−1.0 (3)
C2'—C1'—C6'—C5'	0.4 (2)	C16'—C17'—C18'—C19'	0.9 (3)
N1'—C1'—C6'—C5'	−179.72 (13)	C16—C17—C18—C19	0.3 (3)
C2'—C1'—C6'—C7'	−179.31 (14)	C15'—C14'—C19'—C18'	−1.2 (2)
N1'—C1'—C6'—C7'	0.5 (2)	O3'—C14'—C19'—C18'	175.61 (14)
C4—C5—C6—C1	−0.7 (2)	C17'—C18'—C19'—C14'	0.1 (2)
C4—C5—C6—C7	−179.63 (15)	C15—C14—C19—C18	−1.0 (2)
C2—C1—C6—C5	0.6 (2)	O3—C14—C19—C18	173.70 (15)
N1—C1—C6—C5	−178.87 (13)	C17—C18—C19—C14	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.85 (2)	2.09 (2)	2.903 (1)	162 (1)
N1′—H1′N···O1′ⁱⁱ	0.86 (2)	2.02 (2)	2.867 (1)	167 (1)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈NO₃P
M_r	339.31
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	10.2986 (13), 10.3540 (12), 17.993 (2)
α, β, γ (°)	86.650 (2), 84.036 (2), 62.429 (2)
V (Å³)	1691.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.50 × 0.40 × 0.25

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.918, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	17593, 8135, 6772
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.00
No. of reflections	8135
No. of parameters	441
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.34

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and 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	0.85 (2)	2.09 (2)	2.903 (1)	162 (1)
N1'—H1'N···O1'ⁱⁱ	0.86 (2)	2.02 (2)	2.867 (1)	167 (1)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Zargaran, P., Ghammamy, S. & Eshtiagh-Hosseini, H. (2010). Acta Cryst. E66, o3357. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar