1,1′-Binaphthyl-2,2′-diyl benzyl­phos­phoramidate

Gowda, R.R.; Ramkumar, V.; Chakraborty, D.

doi:10.1107/S1600536811046861

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3310

https://doi.org/10.1107/S1600536811046861

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1,1′-Binaphthyl-2,2′-diyl benzylphosphoramidate

Ravikumar R Gowda,^a Venkatachalam Ramkumar ^a and Debashis Chakraborty ^a ^*

^aDepartment of Chemistry, IIT Madras, Chennai, TamilNadu, India
^*Correspondence e-mail: dchakraborty@iitm.ac.in

(Received 28 October 2011; accepted 7 November 2011; online 16 November 2011)

In the title compound, C₂₇H₂₀NO₃P, the P atom exhibits a somewhat distorted PNO₃ tetrahedral geometry, with the O—P—O angle for the binaphthyl fragment being 102.82 (6)°. The dihedral angle between the naphthyl ring systems is 59.00 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For background to organophosphorus chemistry, see: Malik et al. (2010 ). For related structures, see: Gowda et al. (2010a ,b , 2011 ).

Experimental

Crystal data

C₂₇H₂₀NO₃P
M_r = 437.41
Monoclinic, P 2₁ /c
a = 13.7998 (4) Å
b = 11.0667 (3) Å
c = 14.7487 (5) Å
β = 112.674 (1)°
V = 2078.31 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 298 K
0.35 × 0.27 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.945, T_max = 0.965
29246 measured reflections
5053 independent reflections
3766 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.03
5053 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.90 (2)	2.01 (2)	2.9015 (17)	170.2 (18)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046861/hb6484sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046861/hb6484Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811046861/hb6484Isup3.cml

checkCIF report

Comment top

In the recent years, we were interested in the chemistry of phosphorus (V) compounds (Malik et al., 2010). One of our major objectives has been the use of such reagents for ring-opening polymerization reactions (Gowda et al., 2011). Recently, we have published two phosphoric acid derivatives (Gowda et al., 2010a,b). The title compound described here is the new benzylphosphoroamidate derived from binol phosphorochloridate and benzyl amine.

The P=O bond length is slightly shorter than the P-O length. All the bond lengths and angles are in agreement with literature precedents (Gowda et al., 2011).

Related literature top

For background to organophosphorus chemistry, see: Malik et al. (2010). For related structures, see: Gowda et al. (2010a,b, 2011).

Experimental top

To a stirred solution of binol (200 mg, 0.69 mmol) in CH₂Cl₂ (20 mL) under nitrogen atm at 0 °C was added triethylamine (2 ml, 13.96 mmol) dropwise. To the above reaction mixture POCl₃ (0.07 mL, 0.69 mmol) was added dropwise, formation of HCl was observed. Reaction mixture stirred at 0 °C for 10 mins up to room temperature and continued stirring for 4 h. To the above reaction mixture benzyl amine (0.38 mL, 3.49 mmol)was added at room temperature and the reaction mixture was stirred for 2.5 h. The reaction mixture was evaporated to dryness. Mass was dissoved in CH₂Cl₂ (30 ml) and washed with water (5 mL) then with saturated brine (5 ml). Organic layer was dried over Na₂SO₄, filtered and evaporated to dryness. This was further purified by column chromatography to yield a colourless solid.

Structure description top

The P=O bond length is slightly shorter than the P-O length. All the bond lengths and angles are in agreement with literature precedents (Gowda et al., 2011).

For background to organophosphorus chemistry, see: Malik et al. (2010). For related structures, see: Gowda et al. (2010a,b, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP of the molecule with atoms represented as 30% probability ellipsoids.

1,1'-Binaphthyl-2,2'-diyl benzylphosphoramidate top

Crystal data top

C₂₇H₂₀NO₃P	F(000) = 912
M_r = 437.41	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9423 reflections
a = 13.7998 (4) Å	θ = 2.4–28.1°
b = 11.0667 (3) Å	µ = 0.16 mm⁻¹
c = 14.7487 (5) Å	T = 298 K
β = 112.674 (1)°	Block, colourless
V = 2078.31 (11) Å³	0.35 × 0.27 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	3766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
phi and ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→18
T_min = 0.945, T_max = 0.965	k = −14→14
29246 measured reflections	l = −17→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0445P)² + 0.951P] where P = (F_o² + 2F_c²)/3
5053 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₇H₂₀NO₃P	V = 2078.31 (11) Å³
M_r = 437.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7998 (4) Å	µ = 0.16 mm⁻¹
b = 11.0667 (3) Å	T = 298 K
c = 14.7487 (5) Å	0.35 × 0.27 × 0.22 mm
β = 112.674 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5053 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3766 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.965	R_int = 0.053
29246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.32 e Å⁻³
5053 reflections	Δρ_min = −0.51 e Å⁻³
293 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.32299 (11)	0.67344 (13)	0.54067 (11)	0.0203 (3)
C2	0.40314 (13)	0.62679 (14)	0.62471 (12)	0.0265 (4)
H2	0.3893	0.6035	0.6791	0.032*
C3	0.50170 (13)	0.61628 (14)	0.62505 (13)	0.0295 (4)
H3	0.5561	0.5897	0.6817	0.035*
C4	0.52293 (12)	0.64488 (13)	0.54141 (13)	0.0260 (4)
C5	0.62343 (13)	0.62768 (15)	0.53816 (15)	0.0354 (4)
H5	0.6783	0.5996	0.5938	0.042*
C6	0.64113 (14)	0.65125 (16)	0.45568 (17)	0.0399 (5)
H6	0.7078	0.6402	0.4553	0.048*
C7	0.55859 (14)	0.69235 (15)	0.37079 (16)	0.0363 (4)
H7	0.5705	0.7067	0.3138	0.044*
C8	0.46115 (13)	0.71132 (14)	0.37106 (13)	0.0275 (4)
H8	0.4074	0.7382	0.3141	0.033*
C9	0.44037 (12)	0.69088 (13)	0.45658 (12)	0.0221 (3)
C10	0.33940 (11)	0.71257 (13)	0.45942 (11)	0.0192 (3)
C11	0.25437 (12)	0.77459 (13)	0.37799 (11)	0.0190 (3)
C12	0.26774 (12)	0.89308 (13)	0.34438 (11)	0.0204 (3)
C13	0.36253 (13)	0.95968 (14)	0.38600 (12)	0.0236 (3)
H13	0.4200	0.9252	0.4357	0.028*
C14	0.37069 (14)	1.07407 (14)	0.35407 (13)	0.0291 (4)
H14	0.4338	1.1158	0.3817	0.035*
C15	0.28496 (15)	1.12864 (15)	0.28029 (13)	0.0339 (4)
H15	0.2910	1.2069	0.2600	0.041*
C16	0.19313 (15)	1.06775 (16)	0.23828 (13)	0.0318 (4)
H16	0.1368	1.1046	0.1889	0.038*
C17	0.18144 (13)	0.94851 (15)	0.26850 (11)	0.0245 (3)
C18	0.08507 (13)	0.88577 (16)	0.22596 (12)	0.0294 (4)
H18	0.0297	0.9207	0.1743	0.035*
C19	0.07260 (12)	0.77502 (16)	0.25975 (12)	0.0269 (4)
H19	0.0088	0.7345	0.2322	0.032*
C20	0.15695 (12)	0.72271 (14)	0.33655 (11)	0.0211 (3)
C21	0.02951 (13)	0.81676 (14)	0.48691 (14)	0.0313 (4)
H21A	0.0745	0.8546	0.4583	0.038*
H21B	0.0593	0.8325	0.5570	0.038*
C22	−0.07845 (12)	0.87219 (13)	0.44285 (12)	0.0246 (3)
C23	−0.11269 (14)	0.93190 (15)	0.35337 (13)	0.0305 (4)
H23	−0.0699	0.9341	0.3177	0.037*
C24	−0.20985 (15)	0.98832 (16)	0.31637 (14)	0.0360 (4)
H24	−0.2317	1.0285	0.2564	0.043*
C25	−0.27378 (14)	0.98487 (16)	0.36827 (15)	0.0376 (4)
H25	−0.3385	1.0238	0.3441	0.045*
C26	−0.24159 (15)	0.92352 (18)	0.45635 (15)	0.0397 (5)
H26	−0.2853	0.9195	0.4910	0.048*
C27	−0.14467 (15)	0.86821 (17)	0.49314 (14)	0.0341 (4)
H27	−0.1235	0.8275	0.5528	0.041*
N1	0.02726 (10)	0.68495 (11)	0.47013 (10)	0.0239 (3)
O1	0.22318 (8)	0.68401 (9)	0.54441 (8)	0.0220 (2)
O2	0.14012 (8)	0.61001 (9)	0.37169 (8)	0.0229 (2)
O3	0.12166 (8)	0.47812 (10)	0.49874 (8)	0.0260 (3)
P1	0.12654 (3)	0.60554 (3)	0.47454 (3)	0.02003 (11)
H1N	−0.0227 (15)	0.6422 (19)	0.4812 (14)	0.038 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0176 (7)	0.0159 (7)	0.0252 (8)	−0.0039 (6)	0.0057 (6)	−0.0015 (6)
C2	0.0310 (9)	0.0196 (8)	0.0227 (8)	−0.0038 (6)	0.0034 (7)	0.0014 (6)
C3	0.0241 (8)	0.0191 (8)	0.0323 (9)	0.0010 (6)	−0.0035 (7)	0.0011 (7)
C4	0.0186 (8)	0.0136 (7)	0.0391 (10)	−0.0006 (6)	0.0036 (7)	−0.0023 (6)
C5	0.0185 (8)	0.0198 (8)	0.0578 (13)	0.0015 (6)	0.0036 (8)	−0.0051 (8)
C6	0.0227 (9)	0.0240 (9)	0.0775 (15)	0.0011 (7)	0.0242 (10)	−0.0060 (9)
C7	0.0344 (10)	0.0246 (9)	0.0605 (13)	0.0016 (7)	0.0300 (10)	0.0000 (8)
C8	0.0256 (8)	0.0188 (7)	0.0418 (10)	0.0011 (6)	0.0170 (8)	0.0013 (7)
C9	0.0187 (7)	0.0118 (7)	0.0345 (9)	−0.0016 (5)	0.0086 (7)	−0.0006 (6)
C10	0.0159 (7)	0.0132 (6)	0.0254 (8)	−0.0021 (5)	0.0046 (6)	−0.0006 (6)
C11	0.0186 (7)	0.0193 (7)	0.0199 (8)	0.0012 (6)	0.0084 (6)	−0.0009 (6)
C12	0.0232 (8)	0.0202 (7)	0.0206 (8)	0.0030 (6)	0.0117 (6)	0.0005 (6)
C13	0.0252 (8)	0.0191 (7)	0.0270 (8)	0.0017 (6)	0.0107 (7)	0.0007 (6)
C14	0.0363 (10)	0.0205 (8)	0.0348 (10)	−0.0020 (7)	0.0184 (8)	−0.0001 (7)
C15	0.0505 (11)	0.0200 (8)	0.0386 (10)	0.0051 (7)	0.0253 (9)	0.0085 (7)
C16	0.0402 (10)	0.0290 (9)	0.0283 (9)	0.0129 (8)	0.0154 (8)	0.0106 (7)
C17	0.0284 (9)	0.0268 (8)	0.0207 (8)	0.0066 (7)	0.0119 (7)	0.0026 (6)
C18	0.0251 (9)	0.0401 (10)	0.0205 (8)	0.0085 (7)	0.0058 (7)	0.0056 (7)
C19	0.0177 (8)	0.0394 (9)	0.0206 (8)	−0.0018 (7)	0.0042 (7)	−0.0033 (7)
C20	0.0213 (8)	0.0230 (8)	0.0201 (8)	−0.0009 (6)	0.0092 (6)	−0.0015 (6)
C21	0.0251 (9)	0.0191 (8)	0.0465 (11)	−0.0031 (6)	0.0103 (8)	−0.0062 (7)
C22	0.0234 (8)	0.0166 (7)	0.0339 (9)	−0.0039 (6)	0.0113 (7)	−0.0057 (6)
C23	0.0343 (10)	0.0269 (8)	0.0359 (10)	−0.0052 (7)	0.0199 (8)	−0.0038 (7)
C24	0.0378 (10)	0.0290 (9)	0.0346 (10)	−0.0013 (8)	0.0067 (8)	0.0018 (8)
C25	0.0254 (9)	0.0303 (9)	0.0520 (12)	0.0013 (7)	0.0094 (9)	−0.0099 (8)
C26	0.0347 (10)	0.0425 (11)	0.0517 (12)	−0.0045 (8)	0.0274 (10)	−0.0111 (9)
C27	0.0376 (10)	0.0350 (10)	0.0339 (10)	−0.0020 (8)	0.0184 (8)	0.0005 (8)
N1	0.0208 (7)	0.0167 (6)	0.0358 (8)	−0.0038 (5)	0.0125 (6)	−0.0014 (5)
O1	0.0190 (5)	0.0248 (5)	0.0214 (6)	−0.0063 (4)	0.0068 (5)	−0.0028 (4)
O2	0.0223 (6)	0.0207 (5)	0.0254 (6)	−0.0069 (4)	0.0089 (5)	−0.0045 (4)
O3	0.0214 (6)	0.0200 (5)	0.0367 (7)	−0.0016 (4)	0.0114 (5)	0.0020 (5)
P1	0.0170 (2)	0.01769 (19)	0.0248 (2)	−0.00387 (14)	0.00742 (16)	−0.00084 (15)

Geometric parameters (Å, º) top

C1—C10	1.373 (2)	C16—C17	1.422 (2)
C1—C2	1.403 (2)	C16—H16	0.9300
C1—O1	1.4043 (18)	C17—C18	1.415 (2)
C2—C3	1.363 (2)	C18—C19	1.359 (2)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.409 (3)	C19—C20	1.399 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.419 (2)	C20—O2	1.4039 (18)
C4—C9	1.422 (2)	C21—N1	1.4778 (19)
C5—C6	1.355 (3)	C21—C22	1.507 (2)
C5—H5	0.9300	C21—H21A	0.9700
C6—C7	1.404 (3)	C21—H21B	0.9700
C6—H6	0.9300	C22—C27	1.382 (2)
C7—C8	1.362 (2)	C22—C23	1.386 (2)
C7—H7	0.9300	C23—C24	1.386 (3)
C8—C9	1.415 (2)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.373 (3)
C9—C10	1.430 (2)	C24—H24	0.9300
C10—C11	1.485 (2)	C25—C26	1.379 (3)
C11—C20	1.370 (2)	C25—H25	0.9300
C11—C12	1.439 (2)	C26—C27	1.378 (3)
C12—C13	1.418 (2)	C26—H26	0.9300
C12—C17	1.421 (2)	C27—H27	0.9300
C13—C14	1.370 (2)	N1—P1	1.6078 (14)
C13—H13	0.9300	N1—H1N	0.90 (2)
C14—C15	1.399 (2)	O1—P1	1.5921 (11)
C14—H14	0.9300	O2—P1	1.5992 (11)
C15—C16	1.356 (3)	O3—P1	1.4625 (11)
C15—H15	0.9300

C10—C1—C2	123.23 (14)	C18—C17—C12	119.77 (14)
C10—C1—O1	120.16 (13)	C18—C17—C16	121.16 (15)
C2—C1—O1	116.56 (14)	C12—C17—C16	119.05 (15)
C3—C2—C1	118.71 (16)	C19—C18—C17	120.69 (15)
C3—C2—H2	120.6	C19—C18—H18	119.7
C1—C2—H2	120.6	C17—C18—H18	119.7
C2—C3—C4	121.42 (15)	C18—C19—C20	119.13 (15)
C2—C3—H3	119.3	C18—C19—H19	120.4
C4—C3—H3	119.3	C20—C19—H19	120.4
C3—C4—C5	122.35 (16)	C11—C20—C19	123.71 (14)
C3—C4—C9	118.95 (14)	C11—C20—O2	118.75 (13)
C5—C4—C9	118.69 (16)	C19—C20—O2	117.53 (13)
C6—C5—C4	121.42 (17)	N1—C21—C22	112.09 (13)
C6—C5—H5	119.3	N1—C21—H21A	109.2
C4—C5—H5	119.3	C22—C21—H21A	109.2
C5—C6—C7	119.85 (16)	N1—C21—H21B	109.2
C5—C6—H6	120.1	C22—C21—H21B	109.2
C7—C6—H6	120.1	H21A—C21—H21B	107.9
C8—C7—C6	120.63 (18)	C27—C22—C23	118.23 (16)
C8—C7—H7	119.7	C27—C22—C21	120.26 (16)
C6—C7—H7	119.7	C23—C22—C21	121.47 (15)
C7—C8—C9	121.15 (17)	C22—C23—C24	120.85 (16)
C7—C8—H8	119.4	C22—C23—H23	119.6
C9—C8—H8	119.4	C24—C23—H23	119.6
C8—C9—C4	118.19 (14)	C25—C24—C23	119.98 (18)
C8—C9—C10	122.24 (14)	C25—C24—H24	120.0
C4—C9—C10	119.56 (14)	C23—C24—H24	120.0
C1—C10—C9	117.58 (14)	C24—C25—C26	119.73 (17)
C1—C10—C11	120.47 (13)	C24—C25—H25	120.1
C9—C10—C11	121.94 (13)	C26—C25—H25	120.1
C20—C11—C12	117.54 (14)	C27—C26—C25	120.07 (17)
C20—C11—C10	120.06 (13)	C27—C26—H26	120.0
C12—C11—C10	122.26 (13)	C25—C26—H26	120.0
C13—C12—C17	118.00 (14)	C26—C27—C22	121.12 (18)
C13—C12—C11	122.95 (14)	C26—C27—H27	119.4
C17—C12—C11	119.01 (14)	C22—C27—H27	119.4
C14—C13—C12	121.03 (15)	C21—N1—P1	124.76 (11)
C14—C13—H13	119.5	C21—N1—H1N	117.2 (13)
C12—C13—H13	119.5	P1—N1—H1N	113.9 (13)
C13—C14—C15	120.62 (16)	C1—O1—P1	121.24 (9)
C13—C14—H14	119.7	C20—O2—P1	118.31 (9)
C15—C14—H14	119.7	O3—P1—O1	118.28 (6)
C16—C15—C14	120.15 (15)	O3—P1—O2	107.13 (6)
C16—C15—H15	119.9	O1—P1—O2	102.82 (6)
C14—C15—H15	119.9	O3—P1—N1	114.72 (7)
C15—C16—C17	121.13 (16)	O1—P1—N1	102.49 (7)
C15—C16—H16	119.4	O2—P1—N1	110.75 (7)
C17—C16—H16	119.4

C10—C1—C2—C3	−2.0 (2)	C11—C12—C17—C18	−1.4 (2)
O1—C1—C2—C3	−179.17 (13)	C13—C12—C17—C16	−0.6 (2)
C1—C2—C3—C4	−3.5 (2)	C11—C12—C17—C16	177.21 (14)
C2—C3—C4—C5	−176.09 (15)	C15—C16—C17—C18	178.83 (16)
C2—C3—C4—C9	2.9 (2)	C15—C16—C17—C12	0.3 (2)
C3—C4—C5—C6	177.34 (16)	C12—C17—C18—C19	2.9 (2)
C9—C4—C5—C6	−1.7 (2)	C16—C17—C18—C19	−175.69 (15)
C4—C5—C6—C7	−0.7 (3)	C17—C18—C19—C20	−0.9 (2)
C5—C6—C7—C8	1.4 (3)	C12—C11—C20—C19	4.2 (2)
C6—C7—C8—C9	0.3 (3)	C10—C11—C20—C19	179.94 (14)
C7—C8—C9—C4	−2.7 (2)	C12—C11—C20—O2	−176.58 (12)
C7—C8—C9—C10	178.63 (15)	C10—C11—C20—O2	−0.8 (2)
C3—C4—C9—C8	−175.75 (14)	C18—C19—C20—C11	−2.8 (2)
C5—C4—C9—C8	3.3 (2)	C18—C19—C20—O2	177.96 (14)
C3—C4—C9—C10	3.0 (2)	N1—C21—C22—C27	82.3 (2)
C5—C4—C9—C10	−177.98 (14)	N1—C21—C22—C23	−100.01 (18)
C2—C1—C10—C9	7.7 (2)	C27—C22—C23—C24	1.4 (2)
O1—C1—C10—C9	−175.23 (12)	C21—C22—C23—C24	−176.33 (15)
C2—C1—C10—C11	−172.53 (14)	C22—C23—C24—C25	−0.4 (3)
O1—C1—C10—C11	4.6 (2)	C23—C24—C25—C26	−1.0 (3)
C8—C9—C10—C1	170.66 (14)	C24—C25—C26—C27	1.4 (3)
C4—C9—C10—C1	−8.0 (2)	C25—C26—C27—C22	−0.4 (3)
C8—C9—C10—C11	−9.1 (2)	C23—C22—C27—C26	−1.0 (3)
C4—C9—C10—C11	172.19 (13)	C21—C22—C27—C26	176.76 (16)
C1—C10—C11—C20	−51.9 (2)	C22—C21—N1—P1	159.02 (12)
C9—C10—C11—C20	127.90 (15)	C10—C1—O1—P1	68.19 (16)
C1—C10—C11—C12	123.65 (16)	C2—C1—O1—P1	−114.53 (13)
C9—C10—C11—C12	−56.6 (2)	C11—C20—O2—P1	76.15 (16)
C20—C11—C12—C13	175.66 (14)	C19—C20—O2—P1	−104.58 (14)
C10—C11—C12—C13	0.0 (2)	C1—O1—P1—O3	76.30 (12)
C20—C11—C12—C17	−2.0 (2)	C1—O1—P1—O2	−41.44 (12)
C10—C11—C12—C17	−177.66 (14)	C1—O1—P1—N1	−156.43 (11)
C17—C12—C13—C14	0.0 (2)	C20—O2—P1—O3	−173.99 (10)
C11—C12—C13—C14	−177.67 (15)	C20—O2—P1—O1	−48.64 (11)
C12—C13—C14—C15	0.8 (2)	C20—O2—P1—N1	60.22 (12)
C13—C14—C15—C16	−1.2 (3)	C21—N1—P1—O3	154.28 (14)
C14—C15—C16—C17	0.6 (3)	C21—N1—P1—O1	24.77 (16)
C13—C12—C17—C18	−179.16 (14)	C21—N1—P1—O2	−84.31 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.90 (2)	2.01 (2)	2.9015 (17)	170.2 (18)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₀NO₃P
M_r	437.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.7998 (4), 11.0667 (3), 14.7487 (5)
β (°)	112.674 (1)
V (Å³)	2078.31 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.27 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.945, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	29246, 5053, 3766
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.03
No. of reflections	5053
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.51

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.90 (2)	2.01 (2)	2.9015 (17)	170.2 (18)

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

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