Diphenyl (benzyl­amido)phosphate

Pourayoubi, M.; Eshtiagh-Hosseini, H.; Zargaran, P.; Divjakovic, V.

doi:10.1107/S1600536809053744

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o204

doi:10.1107/S1600536809053744

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Diphenyl (benzylamido)phosphate

Mehrdad Pourayoubi,^a ^* Hossein Eshtiagh-Hosseini,^a Poorya Zargaran ^a and Vladimir Divjakovic ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Physics, Faculty of Sciences, University of Novi Sad, Trg D. Obradovica 3, 21000 Novi Sad, Serbia
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 29 November 2009; accepted 14 December 2009; online 19 December 2009)

The title compound, C₁₉H₁₈NO₃P, was prepared by the reaction of diphenyl phosphorochloridate and benzylamine. In the crystal structure, molecules are linked via N—H⋯O=P hydrogen bonds into extended chains parallel to the c axis.

Related literature

For related structures, see: Bao & Wulff (1993 ); Gholivand et al. (2005 ); Karolak-Wojciechowska et al. (1979 ).

Experimental

Crystal data

C₁₉H₁₈NO₃P
M_r = 339.31
Monoclinic, P 2₁ /c
a = 10.0226 (5) Å
b = 19.2450 (8) Å
c = 10.2273 (5) Å
β = 115.375 (6)°
V = 1782.38 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 295 K
0.43 × 0.28 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.977, T_max = 1.000
8248 measured reflections
4105 independent reflections
2568 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.102
S = 0.91
4105 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯O3ⁱ	0.86	1.97	2.8241 (15)	175
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053744/lh2963sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053744/lh2963Isup2.hkl

checkCIF report

Comment top

In previous work, the synthesis and X-ray structures of some amidophosphoric acid ester compounds, such as [(C₆H₅)(CH₃)CH—NH]P(O)(p—OC₆H₄CH₃)₂ (Gholivand et al., 2005) and P(O)[OC₆H₅]₂[N(CH₂C₆H₅)(C(S)NHCH₂C₆H₅)] (Karolak-Wojciechowska et al., 1979) have been investigated. We report here on the synthesis and crystal structure of a new amido bis(phosphoric acid ester) compound, [C₆H₅—CH₂—NH]P(O)[O—C₆H₅]₂. The title compound was synthesized from the reaction of diphenyl phosphorochloridate with an excess amount of benzylamine. The P—O3 bond length of 1.4567 (10) Å and the P—N bond length of 1.5952 (14) Å are standard for this type of compound [for example for two crystallographically different [(C₆H₅)(CH₃)CH—NH]P(O)(p—OC₆H₄CH₃)₂ molecules (Gholivand et al., 2005), P═O = 1.462 (3) Å and 1.469 (3) Å and P—N = 1.610 (5) Å and 1.614 (5) Å and for the heterocyclic phosphorus compound obtained from sequential treatment of (+)2,2'-diphenyl-3,3'-biphenanthrol with phosphorus oxychloride and (S)-(-)-α-methylbenzylamine (Bao & Wulff, 1993) P═O = 1.456 (6) Å, P—N = 1.612 (7)]. In the title copmound, the P—O1 and P—O2 bond lengths are slightly different (1.5844 (12) Å and 1.5880 (12) Å) and the P atom has a distorted tetrahedral configuration (Fig. 1); the bond angles around the P atom are in the range of 98.80 (6)° [for the O1—P—O2 angle] to 114.84 (7)° [for the O3—P—O1 angle]. Molecules are linked via N—H···O═P hydrogen bonds (N···O3 = 2.8241 (15) Å) into extended chains parallel to the c axis (Fig. 2).

Related literature top

For related structures, see: Bao & Wulff (1993); Gholivand et al. (2005); Karolak-Wojciechowska et al. (1979).

Experimental top

To a solution of diphenyl phosphorochloridate (0.572 g, 2.13 mmol) in chloroform (15 ml), a solution of benzylamine (0.456 g, 4.26 mmol) in chloroform (30 ml) was added at 273K. After 4 h of stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in chloroform and n-heptane (4:1) after slow evaporation at room temperature. IR (KBr, cm^-1): 3165 s, 2891 m, 2680 w, 2221 w, 1952 w, 1592 m, 1475 s, 1242 vs, 1198 vs, 1116 s, 1004 m, 931 vs, 759 s, 687 s.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, indicating the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Diphenyl (benzylamido)phosphate top

Crystal data top

C₁₉H₁₈NO₃P	F(000) = 712
M_r = 339.31	D_x = 1.264 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3418 reflections
a = 10.0226 (5) Å	θ = 3.2–29.1°
b = 19.2450 (8) Å	µ = 0.17 mm⁻¹
c = 10.2273 (5) Å	T = 295 K
β = 115.375 (6)°	Prism, colorless
V = 1782.38 (17) Å³	0.43 × 0.28 × 0.17 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector	4105 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 16.3280 pixels mm^-1	θ_max = 29.2°, θ_min = 3.2°
ω scans	h = −7→13
Absorption correction: multi-scan CrysAlis (Oxford Diffraction, 2009)	k = −17→24
T_min = 0.977, T_max = 1.000	l = −13→13
8248 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.102	w = 1/[σ²(F_o²) + (0.0573P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
4105 reflections	Δρ_max = 0.19 e Å⁻³
218 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (10)

Crystal data top

C₁₉H₁₈NO₃P	V = 1782.38 (17) Å³
M_r = 339.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0226 (5) Å	µ = 0.17 mm⁻¹
b = 19.2450 (8) Å	T = 295 K
c = 10.2273 (5) Å	0.43 × 0.28 × 0.17 mm
β = 115.375 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector	4105 independent reflections
Absorption correction: multi-scan CrysAlis (Oxford Diffraction, 2009)	2568 reflections with I > 2σ(I)
T_min = 0.977, T_max = 1.000	R_int = 0.019
8248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 0.91	Δρ_max = 0.19 e Å⁻³
4105 reflections	Δρ_min = −0.31 e Å⁻³
218 parameters

Special details top

Experimental. #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 47.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 - 37.0000 300.0000 98

#__ type_ start__ end____ width___ exp.time_ 2 omega 5.00 91.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 77.0000 150.0000 86

#__ type_ start__ end____ width___ exp.time_ 3 omega -6.00 41.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 - 77.0000 240.0000 47

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
P	0.97981 (4)	0.22655 (2)	0.06013 (4)	0.04171 (14)
O1	0.87224 (12)	0.16886 (6)	−0.04116 (11)	0.0509 (3)
O2	1.13289 (12)	0.18955 (6)	0.09457 (11)	0.0514 (3)
O3	0.95622 (13)	0.24405 (6)	0.18721 (10)	0.0563 (3)
N	0.97260 (16)	0.29192 (7)	−0.03860 (13)	0.0491 (4)
H	0.9660	0.2836	−0.1238	0.059*
C17	1.2659 (3)	0.00509 (17)	0.3197 (5)	0.1137 (12)
H17	1.2997	−0.0363	0.3701	0.136*
C2	0.84557 (18)	0.40475 (9)	−0.10133 (16)	0.0458 (4)
C1	0.97616 (19)	0.36437 (9)	0.00303 (17)	0.0507 (4)
H1A	1.0661	0.3856	0.0084	0.061*
H1B	0.9782	0.3667	0.0986	0.061*
C8	0.71826 (18)	0.17787 (9)	−0.09973 (17)	0.0490 (4)
C14	1.17229 (17)	0.12655 (9)	0.17145 (18)	0.0495 (4)
C13	0.6460 (2)	0.20013 (13)	−0.2392 (2)	0.0841 (7)
H13	0.6973	0.2108	−0.2939	0.101*
C3	0.7036 (2)	0.38616 (11)	−0.1264 (2)	0.0617 (5)
H3	0.6885	0.3474	−0.0802	0.074*
C7	0.8641 (2)	0.46219 (10)	−0.17277 (18)	0.0576 (5)
H7	0.9585	0.4753	−0.1589	0.069*
C9	0.6453 (2)	0.16092 (11)	−0.0180 (2)	0.0638 (5)
H9	0.6972	0.1456	0.0768	0.077*
C15	1.2344 (2)	0.12743 (12)	0.3197 (2)	0.0668 (5)
H15	1.2451	0.1690	0.3697	0.080*
C5	0.6047 (2)	0.48142 (13)	−0.2871 (2)	0.0779 (6)
H5	0.5239	0.5074	−0.3487	0.094*
C19	1.1552 (2)	0.06622 (12)	0.0974 (2)	0.0756 (6)
H19	1.1122	0.0662	−0.0032	0.091*
C6	0.7436 (2)	0.50035 (11)	−0.2647 (2)	0.0735 (6)
H6	0.7576	0.5392	−0.3116	0.088*
C10	0.4937 (2)	0.16685 (13)	−0.0781 (3)	0.0870 (7)
H10	0.4423	0.1553	−0.0240	0.104*
C18	1.2022 (3)	0.00495 (13)	0.1733 (5)	0.1065 (10)
H18	1.1901	−0.0367	0.1234	0.128*
C4	0.5843 (2)	0.42419 (14)	−0.2187 (2)	0.0765 (6)
H4	0.4893	0.4109	−0.2347	0.092*
C16	1.2806 (3)	0.06559 (18)	0.3931 (3)	0.0959 (9)
H16	1.3221	0.0652	0.4937	0.115*
C11	0.4196 (3)	0.18955 (14)	−0.2160 (4)	0.1061 (10)
H11	0.3173	0.1937	−0.2562	0.127*
C12	0.4943 (3)	0.20642 (15)	−0.2968 (3)	0.1170 (11)
H12	0.4423	0.2222	−0.3912	0.140*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0509 (2)	0.0414 (3)	0.0336 (2)	0.0017 (2)	0.01886 (17)	0.0016 (2)
O1	0.0523 (7)	0.0403 (7)	0.0545 (6)	0.0012 (5)	0.0175 (5)	−0.0030 (5)
O2	0.0500 (6)	0.0496 (8)	0.0554 (6)	0.0035 (6)	0.0234 (5)	0.0076 (6)
O3	0.0751 (8)	0.0621 (9)	0.0367 (6)	0.0050 (7)	0.0287 (5)	0.0045 (6)
N	0.0775 (9)	0.0403 (9)	0.0341 (6)	0.0033 (7)	0.0283 (6)	−0.0005 (6)
C17	0.0716 (17)	0.080 (2)	0.198 (4)	0.0297 (16)	0.067 (2)	0.068 (3)
C2	0.0540 (9)	0.0409 (10)	0.0455 (8)	−0.0013 (8)	0.0242 (7)	−0.0057 (8)
C1	0.0614 (10)	0.0417 (11)	0.0466 (9)	−0.0041 (9)	0.0210 (8)	−0.0025 (8)
C8	0.0525 (10)	0.0325 (10)	0.0494 (9)	−0.0007 (8)	0.0097 (8)	−0.0013 (8)
C14	0.0388 (8)	0.0452 (11)	0.0628 (11)	0.0030 (8)	0.0202 (8)	0.0040 (9)
C13	0.0884 (16)	0.0824 (17)	0.0522 (11)	−0.0214 (13)	0.0022 (10)	0.0109 (11)
C3	0.0655 (12)	0.0597 (13)	0.0704 (11)	−0.0050 (10)	0.0390 (10)	0.0001 (10)
C7	0.0605 (11)	0.0512 (12)	0.0630 (11)	−0.0032 (10)	0.0282 (9)	0.0037 (10)
C9	0.0561 (11)	0.0623 (14)	0.0643 (10)	−0.0019 (10)	0.0177 (9)	−0.0007 (10)
C15	0.0664 (11)	0.0729 (15)	0.0637 (11)	0.0193 (11)	0.0305 (9)	0.0141 (11)
C5	0.0683 (14)	0.0810 (18)	0.0751 (14)	0.0245 (13)	0.0216 (11)	0.0064 (13)
C19	0.0555 (11)	0.0584 (15)	0.0963 (15)	0.0033 (11)	0.0167 (10)	−0.0175 (13)
C6	0.0884 (16)	0.0574 (14)	0.0726 (13)	0.0109 (12)	0.0325 (12)	0.0164 (11)
C10	0.0579 (13)	0.0773 (18)	0.1166 (18)	−0.0056 (12)	0.0286 (13)	−0.0169 (15)
C18	0.0680 (15)	0.0452 (16)	0.190 (3)	0.0061 (13)	0.0401 (19)	−0.005 (2)
C4	0.0524 (11)	0.0902 (18)	0.0894 (14)	0.0068 (12)	0.0326 (11)	−0.0006 (14)
C16	0.0857 (16)	0.116 (2)	0.0997 (17)	0.0436 (17)	0.0529 (14)	0.0563 (19)
C11	0.0530 (13)	0.0567 (16)	0.153 (3)	−0.0022 (12)	−0.0092 (16)	0.0056 (17)
C12	0.093 (2)	0.090 (2)	0.0937 (18)	−0.0231 (16)	−0.0313 (15)	0.0330 (15)

Geometric parameters (Å, º) top

P—O3	1.4567 (10)	C3—C4	1.375 (3)
P—O1	1.5844 (12)	C3—H3	0.9300
P—O2	1.5880 (12)	C7—C6	1.381 (3)
P—N	1.5952 (14)	C7—H7	0.9300
O1—C8	1.4065 (19)	C9—C10	1.379 (3)
O2—C14	1.406 (2)	C9—H9	0.9300
N—C1	1.454 (2)	C15—C16	1.377 (3)
N—H	0.8600	C15—H15	0.9300
C17—C18	1.353 (4)	C5—C6	1.360 (3)
C17—C16	1.359 (4)	C5—C4	1.366 (3)
C17—H17	0.9300	C5—H5	0.9300
C2—C3	1.381 (2)	C19—C18	1.379 (4)
C2—C7	1.381 (2)	C19—H19	0.9300
C2—C1	1.503 (2)	C6—H6	0.9300
C1—H1A	0.9700	C10—C11	1.355 (4)
C1—H1B	0.9700	C10—H10	0.9300
C8—C13	1.363 (2)	C18—H18	0.9300
C8—C9	1.365 (3)	C4—H4	0.9300
C14—C19	1.356 (3)	C16—H16	0.9300
C14—C15	1.370 (2)	C11—C12	1.370 (4)
C13—C12	1.381 (3)	C11—H11	0.9300
C13—H13	0.9300	C12—H12	0.9300

O3—P—O1	114.84 (7)	C2—C7—H7	119.7
O3—P—O2	114.62 (6)	C6—C7—H7	119.7
O1—P—O2	98.80 (6)	C8—C9—C10	119.0 (2)
O3—P—N	113.69 (7)	C8—C9—H9	120.5
O1—P—N	107.77 (6)	C10—C9—H9	120.5
O2—P—N	105.75 (7)	C14—C15—C16	118.7 (2)
C8—O1—P	120.47 (10)	C14—C15—H15	120.7
C14—O2—P	121.58 (10)	C16—C15—H15	120.7
C1—N—P	125.61 (10)	C6—C5—C4	119.8 (2)
C1—N—H	117.2	C6—C5—H5	120.1
P—N—H	117.2	C4—C5—H5	120.1
C18—C17—C16	120.1 (3)	C14—C19—C18	119.2 (2)
C18—C17—H17	120.0	C14—C19—H19	120.4
C16—C17—H17	120.0	C18—C19—H19	120.4
C3—C2—C7	118.08 (17)	C5—C6—C7	120.3 (2)
C3—C2—C1	120.83 (16)	C5—C6—H6	119.8
C7—C2—C1	121.08 (16)	C7—C6—H6	119.8
N—C1—C2	112.54 (13)	C11—C10—C9	119.9 (2)
N—C1—H1A	109.1	C11—C10—H10	120.1
C2—C1—H1A	109.1	C9—C10—H10	120.1
N—C1—H1B	109.1	C17—C18—C19	120.4 (3)
C2—C1—H1B	109.1	C17—C18—H18	119.8
H1A—C1—H1B	107.8	C19—C18—H18	119.8
C13—C8—C9	122.16 (18)	C5—C4—C3	120.2 (2)
C13—C8—O1	118.58 (17)	C5—C4—H4	119.9
C9—C8—O1	119.17 (15)	C3—C4—H4	119.9
C19—C14—C15	121.14 (19)	C17—C16—C15	120.5 (3)
C19—C14—O2	119.20 (16)	C17—C16—H16	119.7
C15—C14—O2	119.57 (17)	C15—C16—H16	119.7
C8—C13—C12	117.9 (2)	C10—C11—C12	120.5 (2)
C8—C13—H13	121.0	C10—C11—H11	119.8
C12—C13—H13	121.0	C12—C11—H11	119.8
C4—C3—C2	120.91 (19)	C11—C12—C13	120.5 (2)
C4—C3—H3	119.5	C11—C12—H12	119.7
C2—C3—H3	119.5	C13—C12—H12	119.7
C2—C7—C6	120.63 (18)

O3—P—O1—C8	56.68 (13)	C3—C2—C7—C6	1.0 (3)
O2—P—O1—C8	179.11 (11)	C1—C2—C7—C6	−177.78 (16)
N—P—O1—C8	−71.14 (13)	C13—C8—C9—C10	−0.4 (3)
O3—P—O2—C14	58.59 (14)	O1—C8—C9—C10	−177.10 (18)
O1—P—O2—C14	−63.99 (12)	C19—C14—C15—C16	0.5 (3)
N—P—O2—C14	−175.37 (11)	O2—C14—C15—C16	−176.02 (16)
O3—P—N—C1	13.52 (17)	C15—C14—C19—C18	−0.5 (3)
O1—P—N—C1	142.00 (14)	O2—C14—C19—C18	176.05 (17)
O2—P—N—C1	−113.09 (14)	C4—C5—C6—C7	−0.3 (3)
P—N—C1—C2	−124.33 (14)	C2—C7—C6—C5	−0.6 (3)
C3—C2—C1—N	60.3 (2)	C8—C9—C10—C11	−0.3 (4)
C7—C2—C1—N	−120.96 (17)	C16—C17—C18—C19	1.7 (4)
P—O1—C8—C13	99.80 (18)	C14—C19—C18—C17	−0.6 (3)
P—O1—C8—C9	−83.34 (19)	C6—C5—C4—C3	0.7 (3)
P—O2—C14—C19	99.71 (17)	C2—C3—C4—C5	−0.2 (3)
P—O2—C14—C15	−83.73 (17)	C18—C17—C16—C15	−1.7 (4)
C9—C8—C13—C12	1.0 (3)	C14—C15—C16—C17	0.6 (3)
O1—C8—C13—C12	177.8 (2)	C9—C10—C11—C12	0.3 (4)
C7—C2—C3—C4	−0.7 (3)	C10—C11—C12—C13	0.4 (4)
C1—C2—C3—C4	178.17 (17)	C8—C13—C12—C11	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O3ⁱ	0.86	1.97	2.8241 (15)	175

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈NO₃P
M_r	339.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.0226 (5), 19.2450 (8), 10.2273 (5)
β (°)	115.375 (6)
V (Å³)	1782.38 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.43 × 0.28 × 0.17

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector
Absorption correction	Multi-scan CrysAlis (Oxford Diffraction, 2009)
T_min, T_max	0.977, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8248, 4105, 2568
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.102, 0.91
No. of reflections	4105
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O3ⁱ	0.86	1.97	2.8241 (15)	174.9

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

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