Diethyl [benzyl­amino­(1,3-diphenyl-1H-pyrazol-4-­yl)meth­yl]phospho­nate

Jagadeesan, G.; Suresh, G.; Nandakumar, B.; Perumal, P.T.; Aravindhan, S.

doi:10.1107/S1600536811032776

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2376

doi:10.1107/S1600536811032776

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Diethyl [benzylamino(1,3-diphenyl-1H-pyrazol-4-yl)methyl]phosphonate

G. Jagadeesan,^a G. Suresh,^a B. Nandakumar,^b P. T. Perumal ^b and S. Aravindhan ^a ^*

^aDepartment of Physics, Presidency College, Chennai 600 005, India, and ^bOrganic Chemistry Laboratory, CLRI, Chennai 600 020, India
^*Correspondence e-mail: aravindhanpresidency@gmail.com

(Received 19 July 2011; accepted 12 August 2011; online 27 August 2011)

In the title compound, C₂₇H₃₀N₃O₃P, the pyrazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and it forms dihedral angles of 9.3 (1) and 40.2 (1)°, respectively, with the phenyl rings attached to the N and C atoms. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by N—H⋯O hydrogen bonds.

Related literature

For the bioactivities of pyrazole derivatives, see: Sullivan et al. (2006 ); Patel et al. (2010 ); Siu et al. (2008 ).

Experimental

Crystal data

C₂₇H₃₀N₃O₃P
M_r = 475.51
Monoclinic, P 2₁ /c
a = 10.9534 (4) Å
b = 9.3777 (3) Å
c = 25.0690 (8) Å
β = 101.233 (2)°
V = 2525.70 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.980, T_max = 0.990
28506 measured reflections
6292 independent reflections
4220 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.03
6292 reflections
403 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 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
N7—H7⋯O2ⁱ	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)
Symmetry code: (i) -x+1, -y+1, -z.

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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811032776/ci5195sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032776/ci5195Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032776/ci5195Isup3.cml

checkCIF report

Comment top

Pyrazoles exhibit a variety of pharmacological properties for e.g antibacterial and anti-inflammatory activities (Sullivan et al., 2006; Patel et al., 2010). One of the pyrazole derivatives shows nucleosidase inhibitory activity against Staphylococcus aureus (Siu et al., 2008). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring is planar; the phenyl ring attached to N3 is almost coplanar [dihedral angle 9.3 (1)°] with it whereas the phenyl attached to C21 is tilted by 40.2 (1)°. Ester substitutions at the P atom lie anti to bulky substitutions at atom C6 [O1—P—C6—N7 = 169.2 (1)° and O3—P—C6—C5 = 175.2 (1)°].

In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by N—H···O hydrogen bonds (Fig. 2).

Related literature top

For the bioactivities of pyrazole derivatives, see: Sullivan et al. (2006); Patel et al. (2010); Siu et al. (2008).

Experimental top

A mixture of 3-diphenyl-1H-pyrazole-4-carbaldehyde (1 mmol), benzyl amine (1 mmol), diethyl phosphate (1.5 mmol) and pottasium hydrogen sulfate (20 mol%) under neat condition was stirred at room temperature. After completion of the reaction as indicated by TLC, it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was chromatographed. Single crystals were grown by slow evaporation an ethyl acetate-petroleum ether solution.

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.
	Fig. 2. A view of the crystal packing. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Diethyl [benzylamino(1,3-diphenyl-1H-pyrazol-4- yl)methyl]phosphonate top

Crystal data top

C₂₇H₃₀N₃O₃P	F(000) = 1008
M_r = 475.51	D_x = 1.251 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8725 reflections
a = 10.9534 (4) Å	θ = 2.8–29.1°
b = 9.3777 (3) Å	µ = 0.14 mm⁻¹
c = 25.0690 (8) Å	T = 293 K
β = 101.233 (2)°	Block, colourless
V = 2525.70 (15) Å³	0.2 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur-S diffractometer	6292 independent reflections
Radiation source: fine-focus sealed tube	4220 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 15.9948 pixels mm^-1	θ_max = 28.4°, θ_min = 2.3°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.980, T_max = 0.990	l = −33→31
28506 measured 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0515P)² + 0.7236P] where P = (F_o² + 2F_c²)/3
6292 reflections	(Δ/σ)_max = 0.001
403 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₇H₃₀N₃O₃P	V = 2525.70 (15) Å³
M_r = 475.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9534 (4) Å	µ = 0.14 mm⁻¹
b = 9.3777 (3) Å	T = 293 K
c = 25.0690 (8) Å	0.2 × 0.2 × 0.2 mm
β = 101.233 (2)°

Data collection top

Oxford Diffraction Xcalibur-S diffractometer	6292 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	4220 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.031
28506 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
6292 reflections	Δρ_min = −0.31 e Å⁻³
403 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
H8B	0.4103 (19)	0.338 (2)	0.1155 (8)	0.066 (6)*
H8A	0.549 (2)	0.373 (2)	0.1466 (8)	0.061 (6)*
H7	0.4879 (18)	0.455 (2)	0.0558 (9)	0.057 (6)*
H17	0.892 (3)	0.223 (3)	−0.0967 (12)	0.098 (9)*
H4	0.6887 (17)	0.4658 (19)	0.0136 (8)	0.046 (5)*
H29B	0.375 (2)	0.800 (3)	0.1338 (10)	0.080 (7)*
H22	0.768 (2)	0.755 (2)	0.1823 (9)	0.073 (7)*
H29A	0.497 (2)	0.891 (2)	0.1420 (9)	0.069 (7)*
H19	1.200 (3)	0.240 (3)	0.0216 (10)	0.095 (9)*
H20	1.085 (2)	0.343 (3)	0.0812 (10)	0.078 (7)*
H14	0.572 (2)	0.522 (3)	0.2261 (10)	0.085 (8)*
H16	0.779 (2)	0.327 (3)	−0.0394 (9)	0.077 (7)*
H10	0.244 (2)	0.501 (3)	0.1297 (10)	0.071 (7)*
H11	0.156 (3)	0.632 (3)	0.1919 (11)	0.103 (10)*
H26	0.930 (2)	0.371 (3)	0.2181 (9)	0.079 (7)*
H18	1.105 (3)	0.180 (3)	−0.0676 (11)	0.096 (8)*
H6	0.5905 (15)	0.6388 (17)	0.1330 (7)	0.036 (4)*
H30A	0.321 (3)	1.032 (3)	0.1460 (13)	0.110 (10)*
H30B	0.252 (3)	0.988 (3)	0.0857 (12)	0.111 (10)*
H27B	0.715 (2)	1.005 (3)	0.0291 (10)	0.087 (8)*
H27A	0.584 (3)	1.038 (3)	0.0488 (11)	0.102 (9)*
H13	0.494 (3)	0.653 (3)	0.2873 (13)	0.113 (11)*
H30C	0.379 (4)	1.079 (5)	0.0955 (17)	0.168 (18)*
H12	0.282 (3)	0.710 (4)	0.2731 (15)	0.146 (13)*
P	0.55474 (4)	0.75862 (4)	0.054083 (18)	0.03871 (13)
O1	0.66355 (11)	0.86067 (11)	0.08051 (5)	0.0448 (3)
N7	0.47930 (14)	0.50807 (15)	0.08404 (6)	0.0428 (3)
N3	0.85342 (13)	0.41796 (14)	0.06060 (6)	0.0420 (3)
O3	0.43152 (11)	0.82882 (13)	0.06482 (5)	0.0491 (3)
N2	0.90518 (14)	0.44221 (15)	0.11333 (6)	0.0451 (4)
O2	0.54283 (13)	0.73175 (13)	−0.00419 (5)	0.0526 (3)
C6	0.58773 (16)	0.60281 (16)	0.09730 (7)	0.0376 (4)
C5	0.71061 (16)	0.53605 (16)	0.09294 (7)	0.0392 (4)
C1	0.81900 (16)	0.51432 (17)	0.13319 (7)	0.0427 (4)
C4	0.73742 (17)	0.47270 (17)	0.04735 (8)	0.0426 (4)
C15	0.92211 (17)	0.34705 (17)	0.02579 (7)	0.0436 (4)
C21	0.84419 (17)	0.5557 (2)	0.19091 (8)	0.0478 (4)
C8	0.4667 (2)	0.41576 (19)	0.12999 (9)	0.0541 (5)
C9	0.4121 (2)	0.49577 (19)	0.17170 (8)	0.0512 (5)
C20	1.0464 (2)	0.3187 (2)	0.04401 (10)	0.0602 (5)
C29	0.4167 (2)	0.8764 (2)	0.11825 (10)	0.0604 (5)
C27	0.6709 (2)	1.0066 (2)	0.06104 (10)	0.0580 (5)
C26	0.9060 (2)	0.4626 (3)	0.23015 (9)	0.0628 (6)
C16	0.8658 (2)	0.3111 (3)	−0.02600 (9)	0.0652 (6)
C14	0.4848 (3)	0.5419 (3)	0.21966 (9)	0.0682 (6)
C23	0.8325 (3)	0.7229 (3)	0.26239 (12)	0.0854 (8)
H23	0.8065	0.8106	0.2734	0.102*
C22	0.8087 (2)	0.6875 (3)	0.20769 (10)	0.0657 (6)
C10	0.2871 (3)	0.5309 (3)	0.16212 (11)	0.0697 (6)
C18	1.0589 (2)	0.2218 (3)	−0.04303 (12)	0.0723 (7)
C17	0.9346 (2)	0.2490 (3)	−0.06048 (11)	0.0760 (7)
C12	0.3125 (4)	0.6572 (4)	0.24570 (13)	0.0964 (10)
C11	0.2376 (3)	0.6101 (3)	0.19938 (15)	0.0875 (9)
C24	0.8937 (3)	0.6297 (4)	0.30026 (11)	0.0899 (9)
H24	0.9102	0.6545	0.3369	0.108*
C19	1.1140 (2)	0.2559 (3)	0.00886 (12)	0.0724 (7)
C28	0.7401 (3)	1.0934 (3)	0.10496 (12)	0.1023 (10)
H28C	0.7453	1.1896	0.0925	0.153*
H28B	0.8225	1.0552	0.1161	0.153*
H28A	0.6982	1.0925	0.1352	0.153*
C30	0.3365 (3)	1.0064 (3)	0.11075 (16)	0.0873 (9)
C13	0.4355 (4)	0.6236 (3)	0.25610 (12)	0.0949 (9)
C25	0.9306 (3)	0.5004 (4)	0.28426 (10)	0.0862 (8)
H25	0.9726	0.4372	0.3101	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0444 (3)	0.0310 (2)	0.0393 (2)	0.00695 (17)	0.00468 (18)	−0.00017 (16)
O1	0.0494 (7)	0.0322 (5)	0.0508 (7)	0.0011 (5)	0.0044 (6)	0.0044 (5)
N7	0.0512 (9)	0.0361 (7)	0.0410 (8)	−0.0005 (6)	0.0088 (7)	−0.0030 (6)
N3	0.0411 (8)	0.0384 (7)	0.0450 (8)	0.0053 (6)	0.0044 (6)	0.0006 (6)
O3	0.0474 (8)	0.0431 (6)	0.0550 (8)	0.0123 (5)	0.0056 (6)	−0.0009 (5)
N2	0.0442 (9)	0.0438 (8)	0.0440 (9)	0.0033 (6)	0.0004 (7)	0.0002 (6)
O2	0.0710 (9)	0.0441 (7)	0.0408 (7)	0.0096 (6)	0.0065 (6)	−0.0016 (5)
C6	0.0439 (10)	0.0321 (7)	0.0357 (9)	0.0042 (6)	0.0048 (7)	−0.0011 (6)
C5	0.0424 (10)	0.0317 (7)	0.0418 (9)	0.0036 (6)	0.0037 (7)	0.0025 (6)
C1	0.0443 (10)	0.0348 (8)	0.0469 (10)	−0.0003 (7)	0.0040 (8)	−0.0002 (7)
C4	0.0426 (10)	0.0398 (8)	0.0427 (10)	0.0076 (7)	0.0017 (8)	0.0021 (7)
C15	0.0429 (10)	0.0368 (8)	0.0523 (11)	0.0032 (7)	0.0121 (8)	0.0028 (7)
C21	0.0404 (10)	0.0528 (10)	0.0485 (11)	−0.0056 (8)	0.0040 (8)	−0.0055 (8)
C8	0.0726 (15)	0.0342 (9)	0.0572 (12)	−0.0024 (9)	0.0168 (11)	0.0030 (8)
C9	0.0660 (13)	0.0407 (9)	0.0493 (11)	−0.0048 (8)	0.0173 (10)	0.0080 (8)
C20	0.0493 (13)	0.0622 (12)	0.0670 (15)	0.0113 (10)	0.0058 (11)	0.0011 (10)
C29	0.0654 (15)	0.0579 (12)	0.0633 (14)	0.0136 (11)	0.0261 (12)	0.0002 (10)
C27	0.0689 (15)	0.0381 (9)	0.0672 (14)	−0.0022 (9)	0.0138 (12)	0.0137 (9)
C26	0.0624 (14)	0.0729 (15)	0.0489 (13)	0.0015 (11)	0.0004 (10)	0.0021 (10)
C16	0.0445 (13)	0.0882 (16)	0.0628 (14)	0.0068 (11)	0.0101 (10)	−0.0175 (12)
C14	0.0804 (18)	0.0683 (14)	0.0539 (14)	0.0128 (12)	0.0081 (12)	0.0023 (10)
C23	0.0794 (18)	0.0889 (18)	0.087 (2)	−0.0169 (14)	0.0155 (15)	−0.0439 (16)
C22	0.0662 (15)	0.0578 (12)	0.0681 (15)	−0.0067 (11)	0.0014 (11)	−0.0192 (11)
C10	0.0709 (17)	0.0727 (15)	0.0675 (16)	−0.0130 (12)	0.0184 (13)	0.0042 (12)
C18	0.0666 (16)	0.0752 (15)	0.0825 (18)	0.0156 (12)	0.0326 (14)	−0.0035 (12)
C17	0.0630 (16)	0.0997 (19)	0.0689 (16)	0.0079 (13)	0.0214 (13)	−0.0199 (14)
C12	0.138 (3)	0.095 (2)	0.0654 (19)	0.030 (2)	0.044 (2)	0.0089 (15)
C11	0.079 (2)	0.0930 (19)	0.103 (2)	0.0139 (16)	0.0481 (19)	0.0228 (17)
C24	0.089 (2)	0.128 (3)	0.0521 (15)	−0.0296 (18)	0.0126 (14)	−0.0301 (16)
C19	0.0474 (14)	0.0824 (16)	0.0898 (19)	0.0193 (12)	0.0191 (13)	0.0060 (13)
C28	0.155 (3)	0.0493 (13)	0.099 (2)	−0.0336 (16)	0.0141 (19)	−0.0041 (13)
C30	0.085 (2)	0.0713 (17)	0.109 (2)	0.0256 (15)	0.028 (2)	−0.0209 (16)
C13	0.130 (3)	0.094 (2)	0.0570 (17)	0.0257 (19)	0.0100 (17)	−0.0089 (14)
C25	0.0901 (19)	0.114 (2)	0.0484 (14)	−0.0115 (16)	−0.0018 (13)	0.0037 (14)

Geometric parameters (Å, º) top

P—O2	1.4629 (13)	C27—H27B	1.02 (3)
P—O1	1.5708 (12)	C27—H27A	0.98 (3)
P—O3	1.5713 (13)	C26—C25	1.377 (3)
P—C6	1.8129 (16)	C26—H26	0.97 (3)
O1—C27	1.460 (2)	C16—C17	1.381 (3)
N7—C6	1.468 (2)	C16—H16	0.96 (2)
N7—C8	1.469 (2)	C14—C13	1.381 (4)
N7—H7	0.89 (2)	C14—H14	0.95 (3)
N3—C4	1.350 (2)	C23—C24	1.366 (4)
N3—N2	1.352 (2)	C23—C22	1.385 (3)
N3—C15	1.423 (2)	C23—H23	0.93
O3—C29	1.451 (2)	C22—H22	0.94 (2)
N2—C1	1.334 (2)	C10—C11	1.384 (4)
C6—C5	1.508 (2)	C10—H10	0.90 (2)
C6—H6	0.952 (17)	C18—C19	1.361 (4)
C5—C4	1.370 (2)	C18—C17	1.370 (4)
C5—C1	1.415 (2)	C18—H18	0.95 (3)
C1—C21	1.472 (3)	C17—H17	0.97 (3)
C4—H4	0.911 (18)	C12—C11	1.359 (5)
C15—C16	1.367 (3)	C12—C13	1.359 (5)
C15—C20	1.375 (3)	C12—H12	0.96 (4)
C21—C22	1.385 (3)	C11—H11	0.90 (3)
C21—C26	1.389 (3)	C24—C25	1.363 (4)
C8—C9	1.502 (3)	C24—H24	0.93
C8—H8B	0.98 (2)	C19—H19	0.94 (3)
C8—H8A	1.00 (2)	C28—H28C	0.96
C9—C14	1.376 (3)	C28—H28B	0.96
C9—C10	1.384 (3)	C28—H28A	0.96
C20—C19	1.387 (3)	C30—H30A	0.96 (3)
C20—H20	0.97 (2)	C30—H30B	1.03 (3)
C29—C30	1.493 (3)	C30—H30C	0.94 (5)
C29—H29B	0.97 (3)	C13—H13	0.95 (3)
C29—H29A	0.97 (2)	C25—H25	0.93
C27—C28	1.458 (3)

O2—P—O1	116.02 (8)	C28—C27—H27A	113.5 (17)
O2—P—O3	109.31 (7)	O1—C27—H27A	105.6 (17)
O1—P—O3	106.20 (7)	H27B—C27—H27A	110 (2)
O2—P—C6	115.25 (7)	C25—C26—C21	120.7 (2)
O1—P—C6	101.10 (7)	C25—C26—H26	121.6 (14)
O3—P—C6	108.25 (8)	C21—C26—H26	117.7 (14)
C27—O1—P	121.11 (13)	C15—C16—C17	119.9 (2)
C6—N7—C8	111.99 (15)	C15—C16—H16	122.0 (14)
C6—N7—H7	108.4 (13)	C17—C16—H16	118.1 (14)
C8—N7—H7	109.5 (13)	C9—C14—C13	121.2 (3)
C4—N3—N2	111.81 (14)	C9—C14—H14	118.3 (15)
C4—N3—C15	127.68 (15)	C13—C14—H14	120.3 (15)
N2—N3—C15	120.46 (14)	C24—C23—C22	120.5 (3)
C29—O3—P	122.76 (13)	C24—C23—H23	119.8
C1—N2—N3	104.94 (14)	C22—C23—H23	119.8
N7—C6—C5	115.25 (13)	C23—C22—C21	120.3 (2)
N7—C6—P	107.10 (11)	C23—C22—H22	118.7 (14)
C5—C6—P	111.61 (12)	C21—C22—H22	121.0 (14)
N7—C6—H6	107.7 (10)	C9—C10—C11	121.0 (3)
C5—C6—H6	110.5 (10)	C9—C10—H10	114.4 (16)
P—C6—H6	104.0 (10)	C11—C10—H10	124.5 (16)
C4—C5—C1	104.24 (15)	C19—C18—C17	119.3 (2)
C4—C5—C6	125.46 (15)	C19—C18—H18	121.5 (16)
C1—C5—C6	130.17 (15)	C17—C18—H18	119.2 (16)
N2—C1—C5	111.30 (15)	C18—C17—C16	120.5 (3)
N2—C1—C21	119.35 (16)	C18—C17—H17	121.1 (17)
C5—C1—C21	129.32 (16)	C16—C17—H17	118.3 (17)
N3—C4—C5	107.71 (16)	C11—C12—C13	120.0 (3)
N3—C4—H4	123.6 (12)	C11—C12—H12	123 (2)
C5—C4—H4	128.7 (12)	C13—C12—H12	117 (2)
C16—C15—C20	120.14 (19)	C12—C11—C10	120.0 (3)
C16—C15—N3	120.21 (17)	C12—C11—H11	120.9 (19)
C20—C15—N3	119.61 (17)	C10—C11—H11	119.0 (19)
C22—C21—C26	118.2 (2)	C25—C24—C23	119.9 (2)
C22—C21—C1	121.60 (18)	C25—C24—H24	120.1
C26—C21—C1	120.17 (18)	C23—C24—H24	120.1
N7—C8—C9	111.25 (15)	C18—C19—C20	121.0 (2)
N7—C8—H8B	107.3 (12)	C18—C19—H19	120.9 (16)
C9—C8—H8B	108.7 (12)	C20—C19—H19	118.1 (16)
N7—C8—H8A	110.5 (12)	C27—C28—H28C	109.5
C9—C8—H8A	111.1 (12)	C27—C28—H28B	109.5
H8B—C8—H8A	107.8 (17)	H28C—C28—H28B	109.5
C14—C9—C10	117.5 (2)	C27—C28—H28A	109.5
C14—C9—C8	121.6 (2)	H28C—C28—H28A	109.5
C10—C9—C8	120.8 (2)	H28B—C28—H28A	109.5
C15—C20—C19	119.1 (2)	C29—C30—H30A	106.8 (19)
C15—C20—H20	119.4 (14)	C29—C30—H30B	112.3 (17)
C19—C20—H20	121.5 (14)	H30A—C30—H30B	108 (2)
O3—C29—C30	107.7 (2)	C29—C30—H30C	109 (3)
O3—C29—H29B	106.8 (14)	H30A—C30—H30C	112 (3)
C30—C29—H29B	109.8 (15)	H30B—C30—H30C	109 (3)
O3—C29—H29A	111.0 (13)	C12—C13—C14	120.2 (3)
C30—C29—H29A	113.8 (14)	C12—C13—H13	125.0 (19)
H29B—C29—H29A	108 (2)	C14—C13—H13	115 (2)
C28—C27—O1	108.98 (18)	C24—C25—C26	120.4 (3)
C28—C27—H27B	110.2 (14)	C24—C25—H25	119.8
O1—C27—H27B	108.5 (14)	C26—C25—H25	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O2ⁱ	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₀N₃O₃P
M_r	475.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.9534 (4), 9.3777 (3), 25.0690 (8)
β (°)	101.233 (2)
V (Å³)	2525.70 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur-S diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	28506, 6292, 4220
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.03
No. of reflections	6292
No. of parameters	403
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O2ⁱ	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

SA thanks the UGC, India, for financial support.

References

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