Diiso­propyl [(2-hydroxy-1-naphthyl)­methyl­]phospho­nate

Zarychta, B.; Zaleski, J.; Gawdzik, B.; Iwanek, W.

doi:10.1107/S160053680301393X

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Diisopropyl [(2-hydroxy-1-naphthyl)methyl]phosphonate

B. Zarychta, J. Zaleski, B. Gawdzik and W. Iwanek

The bond lengths and angles in the title compound, C₁₇H₂₃PO₄, are in accordance with anticipated values. There are two conformers in the asymmetric unit. They differ from each other in the orientation of the C and P tetrahedra. Analysis of the structure does not reveal any significant differences between the bond distances and angles of the molecules in the asymmetric unit. In the crystal structure, the conformers are linked by O—H

O=P and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301393X/bt6291sup1.cif Contains datablocks global, II
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301393X/bt6291IIsup2.hkl Contains datablock II

CCDC reference: 217617

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.043
wR factor = 0.084
Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



CHEMS_01  Alert B The sum formula contains elements in the wrong order.
          P  precedes O
          Sequence must be C, H, then alphabetical.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.99
         From the CIF: _reflns_number_total               6056
         Count of symmetry unique reflns         3148
         Completeness (_total/calc)            192.38%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2908
         Fraction of Friedel pairs measured     0.924
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

Phosphorus derivatives are an important class of biologically active compounds (Kabacnik, 1987). The reaction of the phenolic Mannich base with trialcoxyphosphites leads to methylen-phosphorous derivatives of phenols (Ivanov & Valitova, 1967; Hahn & Weglewski, 1968; Rupp & Heiner, 1982). In our investigations, we used a β-naphthol derivative of L-proline, (I), and triisopropyl phosphite. In this paper, we present X-ray crystallographic analysis of the title compound, (II).

The presence of a stereogenic centre in derivative (I) creates the possibility of stereoselective synthesis of chiral phosphorous derivatives; this is still under the investigation.

The title compound crystallizes in the space group P2₁, with two nearly centrosymmetrically related molecules. The two independent conformers, A and B, are shown in Fig. 1. In conformer A, the dihedral angle between planes C2–C1–C11 and C1–C11–P1 is 88.2 (3)°, while in the conformer B it is −88.6 (3)°. This corresponds with the twist of the —CPO(OC₃H₇)₂ and hydroxynaphthyl groups of 176.8 (3)° between the two conformers. Analysis of the structure does not reveal significant differences in the bond distances and angles of the two molecules in the asymmetric unit. The most significant deviations in bond lengths between the two conformers are 0.026 (4) and 0.023 (5) Å for C1–C2 and C2–C3, respectively. The 2-hydroxynaphthyl group is nearly planar. The torsion angles which most deviate from 0° or 180° are C9—C1—C2—O4 [−177.3 (3)°] and C9'-C1'-C2'-O4' [177.3 (2)°] (Table 1.). The bond lengths and angles in the structure are in accordance with anticipated values (Tahar et al., 1996; Langley et al. 1996). In these compounds, there is a characteristic pattern of torsion angles and of the orientation of the C and P tetrahedra (Ružić-Toroš & Kojić-Prodić, 1978). The aromatic system and O2(') are anti to each other [O2–P1–C11–C1 = 178.6 (2) and O2'–P1'–C11'–C1' = 179.4 (2)°], while the P—C bond is perpendicular to the plane of hydroxynaphthyl group in both conformers (Benedetto et al., 1997). No H atoms were located in the region of O3 or O3'. In the crystal structure, conformers A and B are linked by O–H···O=P hydrogen bonds, leading to dimerization (Figure 2.). Those dimers are joined by weak C—H···O hydrogen bonds (Table 2.).

Experimental top

A solution of compound (I) and P[OCH(CH₃)₂]₃ was heated to reflux in toluene for 4 h. The resulting solution was evaporated and acetonitrile was added. After 24 h, compound (II) crystallized with a yield 75%. The determined melting point is 398–399 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL9.

Figures top

	Fig. 1. The molecular structure of the title compound. There are two independent conformers, A and B, in the unit cell. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

(II) top

Crystal data top

C₁₇H₂₃PO₄	F(000) = 688
M_r = 322.32	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6056 reflections
a = 9.166 (1) Å	θ = 3.6–25.0°
b = 22.484 (2) Å	µ = 0.17 mm⁻¹
c = 9.579 (1) Å	T = 293 K
β = 118.21 (1)°	Irregular, colourless
V = 1739.7 (3) Å³	0.2 × 0.15 × 0.1 mm
Z = 4

Data collection top

Xcalibur diffractometer	6056 independent reflections
Radiation source: fine-focus sealed tube	4614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θ_max = 25.0°, θ_min = 3.6°
ω–scan	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −26→26
T_min = 0.966, T_max = 0.979	l = −11→6
10929 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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0387P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
6056 reflections	Δρ_max = 0.15 e Å⁻³
463 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

C₁₇H₂₃PO₄	V = 1739.7 (3) Å³
M_r = 322.32	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 9.166 (1) Å	µ = 0.17 mm⁻¹
b = 22.484 (2) Å	T = 293 K
c = 9.579 (1) Å	0.2 × 0.15 × 0.1 mm
β = 118.21 (1)°

Data collection top

Xcalibur diffractometer	6056 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4614 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.979	R_int = 0.029
10929 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	Δρ_max = 0.15 e Å⁻³
S = 1.00	Δρ_min = −0.21 e Å⁻³
6056 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
463 parameters	Absolute structure parameter: 0.00 (8)
1 restraint

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	0.80393 (9)	0.27391 (3)	0.14087 (8)	0.0365 (2)
O1	0.9884 (2)	0.25154 (8)	0.2243 (2)	0.0418 (5)
O2	0.7106 (3)	0.23366 (10)	−0.0097 (2)	0.0470 (6)
O3	0.7897 (3)	0.33771 (9)	0.1070 (2)	0.0484 (6)
O4	0.5684 (3)	0.34736 (10)	0.2986 (3)	0.0542 (6)
H4A	0.536 (5)	0.3790 (18)	0.310 (4)	0.081*
C1	0.7926 (4)	0.28200 (14)	0.4204 (3)	0.0388 (8)
C2	0.7139 (4)	0.33292 (14)	0.4252 (4)	0.0437 (8)
C3	0.7848 (6)	0.36989 (16)	0.5611 (5)	0.0603 (11)
H3A	0.725 (5)	0.4000 (17)	0.560 (4)	0.072*
C4	0.9293 (6)	0.35468 (17)	0.6876 (5)	0.0637 (11)
H4B	0.979 (4)	0.3796 (16)	0.773 (4)	0.076*
C5	1.1619 (6)	0.2850 (2)	0.8213 (5)	0.0690 (13)
H5A	1.193 (5)	0.3134 (17)	0.898 (4)	0.083*
C6	1.2397 (6)	0.2341 (2)	0.8239 (5)	0.0782 (13)
H6A	1.345 (5)	0.2200 (18)	0.908 (5)	0.094*
C7	1.1688 (5)	0.1961 (2)	0.6913 (5)	0.0659 (11)
H7A	1.225 (5)	0.1610 (17)	0.691 (4)	0.079*
C8	1.0269 (5)	0.21071 (16)	0.5624 (4)	0.0501 (9)
H8A	0.979 (4)	0.1866 (15)	0.478 (4)	0.060*
C9	0.9425 (4)	0.26435 (13)	0.5546 (3)	0.0393 (8)
C10	1.0125 (4)	0.30172 (16)	0.6900 (4)	0.0495 (9)
C11	0.7212 (4)	0.24748 (15)	0.2663 (4)	0.0383 (8)
H11A	0.753 (3)	0.2025 (14)	0.286 (3)	0.046*
H11B	0.608 (4)	0.2560 (13)	0.209 (3)	0.046*
C12	1.1294 (4)	0.28735 (16)	0.2418 (4)	0.0478 (9)
H12A	1.096 (4)	0.3118 (14)	0.146 (4)	0.057*
C13	1.1815 (5)	0.32914 (17)	0.3803 (4)	0.0665 (11)
H13A	1.0909	0.3550	0.3626	0.100*
H13B	1.2740	0.3525	0.3913	0.100*
H13C	1.2128	0.3066	0.4754	0.100*
C14	1.2607 (4)	0.24318 (18)	0.2635 (5)	0.0728 (12)
H14A	1.2321	0.2241	0.1642	0.109*
H14B	1.2694	0.2138	0.3398	0.109*
H14C	1.3649	0.2633	0.3004	0.109*
C15	0.7457 (4)	0.24166 (17)	−0.1441 (4)	0.0492 (9)
H15A	0.825 (4)	0.2787 (15)	−0.125 (3)	0.059*
C16	0.8368 (6)	0.18832 (18)	−0.1534 (5)	0.0763 (13)
H16A	0.9331	0.1821	−0.0529	0.114*
H16B	0.8701	0.1943	−0.2335	0.114*
H16C	0.7660	0.1541	−0.1797	0.114*
C17	0.5847 (5)	0.2523 (3)	−0.2885 (4)	0.0993 (18)
H17A	0.5304	0.2858	−0.2714	0.149*
H17B	0.5159	0.2177	−0.3104	0.149*
H17C	0.6041	0.2601	−0.3769	0.149*
P1'	0.56977 (10)	0.01555 (4)	0.70498 (9)	0.0395 (2)
O1'	0.7551 (2)	0.03493 (8)	0.7918 (2)	0.0422 (5)
O2'	0.4823 (3)	0.05866 (10)	0.5598 (2)	0.0509 (6)
O3'	0.5477 (3)	−0.04770 (9)	0.6633 (3)	0.0532 (6)
O4'	0.3312 (3)	−0.05856 (10)	0.8586 (3)	0.0516 (6)
H4C	0.303 (4)	−0.0958 (17)	0.866 (4)	0.077*
C1'	0.5581 (4)	0.00600 (13)	0.9840 (3)	0.0367 (7)
C2'	0.4760 (4)	−0.04524 (14)	0.9877 (4)	0.0416 (8)
C3'	0.5416 (5)	−0.08186 (15)	1.1223 (4)	0.0539 (9)
H3B	0.479 (4)	−0.1194 (16)	1.122 (4)	0.065*
C4'	0.6855 (5)	−0.06769 (15)	1.2494 (5)	0.0580 (10)
H4D	0.714 (4)	−0.0938 (16)	1.333 (4)	0.070*
C5'	0.9258 (5)	−0.00020 (18)	1.3880 (4)	0.0625 (11)
H5B	0.970 (4)	−0.0336 (17)	1.480 (4)	0.075*
C6'	1.0070 (5)	0.0504 (2)	1.3888 (5)	0.0683 (12)
H6B	1.114 (5)	0.0600 (16)	1.483 (4)	0.082*
C7'	0.9401 (5)	0.08862 (19)	1.2575 (5)	0.0601 (10)
H7B	1.003 (4)	0.1274 (17)	1.273 (4)	0.072*
C8'	0.7954 (5)	0.07504 (16)	1.1284 (4)	0.0480 (9)
H8B	0.753 (4)	0.1001 (14)	1.038 (4)	0.058*
C9'	0.7066 (4)	0.02249 (13)	1.1199 (3)	0.0401 (7)
C10'	0.7731 (4)	−0.01565 (15)	1.2538 (4)	0.0501 (9)
C11'	0.4885 (4)	0.04128 (15)	0.8316 (4)	0.0428 (8)
H11C	0.369 (4)	0.0387 (13)	0.769 (3)	0.051*
H11D	0.514 (4)	0.0833 (14)	0.846 (3)	0.051*
C12'	0.8955 (4)	−0.00166 (15)	0.8077 (4)	0.0472 (9)
H12B	0.851 (4)	−0.0226 (15)	0.703 (4)	0.057*
C13'	0.9469 (5)	−0.04302 (17)	0.9461 (4)	0.0683 (11)
H13D	0.8546	−0.0675	0.9307	0.102*
H13E	0.9830	−0.0202	1.0415	0.102*
H13F	1.0360	−0.0678	0.9545	0.102*
C14'	1.0271 (4)	0.04136 (19)	0.8246 (5)	0.0753 (13)
H14D	0.9811	0.0702	0.7410	0.113*
H14E	1.1152	0.0203	0.8187	0.113*
H14F	1.0696	0.0612	0.9251	0.113*
C15'	0.5190 (4)	0.05305 (17)	0.4257 (4)	0.0504 (9)
H15B	0.591 (4)	0.0156 (16)	0.450 (3)	0.061*
C16'	0.5995 (6)	0.10896 (19)	0.4154 (5)	0.0832 (13)
H16D	0.7065	0.1124	0.5067	0.125*
H16E	0.5322	0.1423	0.4116	0.125*
H16F	0.6117	0.1084	0.3213	0.125*
C17'	0.3609 (5)	0.0393 (3)	0.2821 (4)	0.1032 (19)
H17D	0.3190	0.0019	0.2960	0.155*
H17E	0.3797	0.0371	0.1918	0.155*
H17F	0.2817	0.0700	0.2656	0.155*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0398 (5)	0.0371 (5)	0.0376 (4)	0.0010 (4)	0.0225 (4)	−0.0007 (4)
O1	0.0382 (13)	0.0395 (12)	0.0507 (12)	−0.0007 (10)	0.0236 (11)	0.0036 (10)
O2	0.0520 (15)	0.0602 (15)	0.0349 (11)	−0.0159 (11)	0.0256 (11)	−0.0099 (11)
O3	0.0590 (15)	0.0397 (13)	0.0590 (13)	0.0098 (11)	0.0383 (12)	0.0087 (11)
O4	0.0582 (16)	0.0465 (15)	0.0632 (15)	0.0094 (13)	0.0331 (14)	0.0029 (13)
C1	0.048 (2)	0.0382 (19)	0.0422 (17)	−0.0066 (16)	0.0315 (17)	−0.0040 (15)
C2	0.057 (2)	0.0370 (19)	0.051 (2)	−0.0039 (17)	0.0374 (19)	−0.0023 (17)
C3	0.080 (3)	0.045 (2)	0.074 (3)	−0.002 (2)	0.052 (3)	−0.008 (2)
C4	0.092 (3)	0.053 (2)	0.054 (2)	−0.017 (2)	0.041 (3)	−0.0183 (19)
C5	0.076 (3)	0.080 (4)	0.051 (2)	−0.015 (3)	0.030 (2)	−0.006 (2)
C6	0.065 (3)	0.102 (4)	0.057 (3)	−0.002 (3)	0.020 (2)	0.010 (3)
C7	0.065 (3)	0.074 (3)	0.060 (3)	0.010 (2)	0.031 (2)	0.010 (2)
C8	0.063 (3)	0.048 (2)	0.045 (2)	0.0014 (19)	0.030 (2)	0.0043 (17)
C9	0.053 (2)	0.0389 (19)	0.0372 (17)	−0.0082 (16)	0.0308 (16)	−0.0022 (14)
C10	0.061 (2)	0.053 (2)	0.0414 (19)	−0.0158 (18)	0.0296 (19)	−0.0045 (17)
C11	0.042 (2)	0.0419 (19)	0.0392 (18)	−0.0036 (16)	0.0263 (17)	−0.0010 (15)
C12	0.0376 (19)	0.062 (3)	0.0469 (19)	−0.0060 (16)	0.0226 (16)	0.0022 (17)
C13	0.062 (3)	0.064 (3)	0.068 (2)	−0.018 (2)	0.026 (2)	−0.015 (2)
C14	0.049 (2)	0.082 (3)	0.095 (3)	0.004 (2)	0.039 (2)	−0.005 (2)
C15	0.061 (2)	0.059 (2)	0.0376 (18)	−0.0126 (19)	0.0316 (19)	−0.0053 (17)
C16	0.119 (4)	0.066 (3)	0.075 (3)	−0.008 (3)	0.072 (3)	−0.011 (2)
C17	0.085 (4)	0.165 (6)	0.044 (2)	0.007 (3)	0.027 (3)	0.012 (3)
P1'	0.0437 (5)	0.0398 (5)	0.0415 (4)	−0.0010 (4)	0.0255 (4)	0.0017 (4)
O1'	0.0352 (12)	0.0419 (12)	0.0526 (12)	0.0021 (9)	0.0233 (10)	−0.0016 (10)
O2'	0.0556 (15)	0.0656 (15)	0.0410 (12)	0.0111 (12)	0.0306 (12)	0.0136 (11)
O3'	0.0686 (16)	0.0409 (14)	0.0655 (14)	−0.0110 (11)	0.0444 (13)	−0.0085 (11)
O4'	0.0523 (15)	0.0434 (14)	0.0657 (15)	−0.0048 (12)	0.0333 (13)	0.0009 (12)
C1'	0.0452 (19)	0.0345 (18)	0.0428 (17)	0.0045 (15)	0.0311 (16)	0.0001 (15)
C2'	0.050 (2)	0.0414 (19)	0.0447 (19)	0.0017 (16)	0.0311 (18)	−0.0013 (16)
C3'	0.075 (3)	0.038 (2)	0.058 (2)	−0.0026 (19)	0.039 (2)	0.0072 (18)
C4'	0.084 (3)	0.041 (2)	0.053 (2)	0.006 (2)	0.036 (2)	0.0122 (18)
C5'	0.074 (3)	0.067 (3)	0.043 (2)	0.011 (2)	0.025 (2)	−0.0022 (19)
C6'	0.060 (3)	0.086 (3)	0.055 (3)	−0.007 (2)	0.023 (2)	−0.024 (3)
C7'	0.069 (3)	0.064 (3)	0.059 (3)	−0.014 (2)	0.039 (2)	−0.015 (2)
C8'	0.062 (3)	0.047 (2)	0.045 (2)	−0.0064 (19)	0.033 (2)	−0.0046 (17)
C9'	0.054 (2)	0.0360 (18)	0.0415 (17)	0.0021 (17)	0.0322 (16)	−0.0039 (15)
C10'	0.064 (2)	0.050 (2)	0.0435 (19)	0.0081 (19)	0.0314 (19)	0.0021 (17)
C11'	0.048 (2)	0.0406 (19)	0.046 (2)	0.0042 (16)	0.0274 (18)	0.0064 (16)
C12'	0.053 (2)	0.047 (2)	0.050 (2)	0.0112 (16)	0.0307 (18)	−0.0005 (16)
C13'	0.071 (3)	0.061 (3)	0.072 (3)	0.021 (2)	0.034 (2)	0.015 (2)
C14'	0.045 (2)	0.092 (3)	0.097 (3)	0.011 (2)	0.040 (2)	0.017 (3)
C15'	0.056 (2)	0.063 (2)	0.0446 (19)	0.0057 (19)	0.0336 (19)	0.0044 (17)
C16'	0.113 (4)	0.079 (3)	0.087 (3)	−0.011 (3)	0.072 (3)	0.006 (2)
C17'	0.079 (3)	0.181 (6)	0.046 (2)	−0.018 (3)	0.026 (2)	−0.013 (3)

Geometric parameters (Å, º) top

P1—O3	1.463 (2)	P1'—O3'	1.465 (2)
P1—O2	1.570 (2)	P1'—O1'	1.559 (2)
P1—O1	1.573 (2)	P1'—O2'	1.569 (2)
P1—C11	1.798 (3)	P1'—C11'	1.793 (3)
O1—C12	1.463 (4)	O1'—C12'	1.474 (4)
O2—C15	1.479 (3)	O2'—C15'	1.480 (3)
O4—C2	1.351 (4)	O4'—C2'	1.352 (4)
O4—H4A	0.80 (4)	O4'—H4C	0.89 (4)
C1—C2	1.366 (4)	C1'—C2'	1.385 (4)
C1—C9	1.424 (4)	C1'—C9'	1.418 (4)
C1—C11	1.515 (4)	C1'—C11'	1.512 (4)
C2—C3	1.418 (5)	C2'—C3'	1.403 (4)
C3—C4	1.350 (6)	C3'—C4'	1.344 (5)
C3—H3A	0.87 (4)	C3'—H3B	1.02 (3)
C4—C10	1.409 (5)	C4'—C10'	1.409 (5)
C4—H4B	0.91 (4)	C4'—H4D	0.92 (4)
C5—C6	1.342 (6)	C5'—C6'	1.358 (5)
C5—C10	1.403 (5)	C5'—C10'	1.425 (5)
C5—H5A	0.91 (4)	C5'—H5B	1.08 (4)
C6—C7	1.409 (6)	C6'—C7'	1.402 (5)
C6—H6A	0.97 (4)	C6'—H6B	0.99 (4)
C7—C8	1.344 (5)	C7'—C8'	1.353 (5)
C7—H7A	0.94 (4)	C7'—H7B	1.02 (4)
C8—C9	1.416 (5)	C8'—C9'	1.415 (5)
C8—H8A	0.90 (3)	C8'—H8B	0.95 (3)
C9—C10	1.419 (4)	C9'—C10'	1.419 (4)
C11—H11A	1.04 (3)	C11'—H11C	0.97 (3)
C11—H11B	0.93 (3)	C11'—H11D	0.97 (3)
C12—C14	1.498 (5)	C12'—C14'	1.493 (5)
C12—C13	1.507 (4)	C12'—C13'	1.501 (5)
C12—H12A	0.98 (3)	C12'—H12B	1.01 (3)
C13—H13A	0.9600	C13'—H13D	0.9600
C13—H13B	0.9600	C13'—H13E	0.9600
C13—H13C	0.9600	C13'—H13F	0.9600
C14—H14A	0.9600	C14'—H14D	0.9600
C14—H14B	0.9600	C14'—H14E	0.9600
C14—H14C	0.9600	C14'—H14F	0.9600
C15—C16	1.488 (5)	C15'—C17'	1.484 (5)
C15—C17	1.489 (5)	C15'—C16'	1.484 (5)
C15—H15A	1.07 (3)	C15'—H15B	1.03 (3)
C16—H16A	0.9600	C16'—H16D	0.9600
C16—H16B	0.9600	C16'—H16E	0.9600
C16—H16C	0.9600	C16'—H16F	0.9600
C17—H17A	0.9600	C17'—H17D	0.9600
C17—H17B	0.9600	C17'—H17E	0.9600
C17—H17C	0.9600	C17'—H17F	0.9600

O3—P1—O2	114.13 (12)	O3'—P1'—O1'	113.07 (13)
O3—P1—O1	112.83 (12)	O3'—P1'—O2'	114.29 (13)
O2—P1—O1	105.69 (12)	O1'—P1'—O2'	105.75 (12)
O3—P1—C11	116.80 (14)	O3'—P1'—C11'	116.71 (15)
O2—P1—C11	101.78 (13)	O1'—P1'—C11'	104.21 (14)
O1—P1—C11	104.28 (14)	O2'—P1'—C11'	101.44 (14)
C12—O1—P1	124.15 (19)	C12'—O1'—P1'	125.27 (19)
C15—O2—P1	118.8 (2)	C15'—O2'—P1'	119.1 (2)
C2—O4—H4A	111 (3)	C2'—O4'—H4C	109 (2)
C2—C1—C9	120.2 (3)	C2'—C1'—C9'	119.4 (3)
C2—C1—C11	118.1 (3)	C2'—C1'—C11'	118.3 (3)
C9—C1—C11	121.7 (3)	C9'—C1'—C11'	122.2 (3)
O4—C2—C1	119.0 (3)	O4'—C2'—C1'	118.1 (3)
O4—C2—C3	120.8 (3)	O4'—C2'—C3'	121.3 (3)
C1—C2—C3	120.2 (3)	C1'—C2'—C3'	120.6 (3)
C4—C3—C2	120.3 (4)	C4'—C3'—C2'	120.3 (3)
C4—C3—H3A	124 (3)	C4'—C3'—H3B	120.7 (19)
C2—C3—H3A	115 (3)	C2'—C3'—H3B	119.0 (19)
C3—C4—C10	121.5 (4)	C3'—C4'—C10'	121.7 (3)
C3—C4—H4B	120 (2)	C3'—C4'—H4D	113 (2)
C10—C4—H4B	118 (2)	C10'—C4'—H4D	125 (2)
C6—C5—C10	122.0 (4)	C6'—C5'—C10'	120.8 (4)
C6—C5—H5A	128 (3)	C6'—C5'—H5B	125.9 (19)
C10—C5—H5A	110 (2)	C10'—C5'—H5B	113.2 (19)
C5—C6—C7	119.1 (4)	C5'—C6'—C7'	120.1 (4)
C5—C6—H6A	127 (2)	C5'—C6'—H6B	119 (2)
C7—C6—H6A	114 (2)	C7'—C6'—H6B	120 (2)
C8—C7—C6	120.8 (4)	C8'—C7'—C6'	120.4 (4)
C8—C7—H7A	120 (2)	C8'—C7'—H7B	125 (2)
C6—C7—H7A	119 (2)	C6'—C7'—H7B	115 (2)
C7—C8—C9	121.6 (4)	C7'—C8'—C9'	122.0 (4)
C7—C8—H8A	122 (2)	C7'—C8'—H8B	120 (2)
C9—C8—H8A	116 (2)	C9'—C8'—H8B	118 (2)
C8—C9—C10	117.2 (3)	C8'—C9'—C10'	117.6 (3)
C8—C9—C1	123.7 (3)	C8'—C9'—C1'	123.2 (3)
C10—C9—C1	119.1 (3)	C10'—C9'—C1'	119.2 (3)
C4—C10—C5	122.2 (4)	C4'—C10'—C9'	118.7 (3)
C4—C10—C9	118.6 (3)	C4'—C10'—C5'	122.2 (3)
C5—C10—C9	119.2 (3)	C9'—C10'—C5'	119.2 (3)
C1—C11—P1	110.9 (2)	C1'—C11'—P1'	111.3 (2)
C1—C11—H11A	111.5 (16)	C1'—C11'—H11C	113.8 (18)
P1—C11—H11A	105.6 (16)	P1'—C11'—H11C	105.6 (18)
C1—C11—H11B	108.4 (18)	C1'—C11'—H11D	114.3 (18)
P1—C11—H11B	103.9 (17)	P1'—C11'—H11D	104.9 (18)
H11A—C11—H11B	116 (2)	H11C—C11'—H11D	106 (3)
O1—C12—C14	105.0 (3)	O1'—C12'—C14'	105.7 (3)
O1—C12—C13	109.8 (3)	O1'—C12'—C13'	109.3 (3)
C14—C12—C13	113.1 (3)	C14'—C12'—C13'	113.9 (3)
O1—C12—H12A	109.6 (18)	O1'—C12'—H12B	103.6 (18)
C14—C12—H12A	111.9 (18)	C14'—C12'—H12B	109.8 (18)
C13—C12—H12A	107.4 (19)	C13'—C12'—H12B	113.7 (19)
C12—C13—H13A	109.5	C12'—C13'—H13D	109.5
C12—C13—H13B	109.5	C12'—C13'—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13'—H13E	109.5
C12—C13—H13C	109.5	C12'—C13'—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13'—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13'—H13F	109.5
C12—C14—H14A	109.5	C12'—C14'—H14D	109.5
C12—C14—H14B	109.5	C12'—C14'—H14E	109.5
H14A—C14—H14B	109.5	H14D—C14'—H14E	109.5
C12—C14—H14C	109.5	C12'—C14'—H14F	109.5
H14A—C14—H14C	109.5	H14D—C14'—H14F	109.5
H14B—C14—H14C	109.5	H14E—C14'—H14F	109.5
O2—C15—C16	108.3 (3)	O2'—C15'—C17'	107.4 (3)
O2—C15—C17	107.5 (3)	O2'—C15'—C16'	108.0 (3)
C16—C15—C17	114.3 (3)	C17'—C15'—C16'	114.4 (4)
O2—C15—H15A	111.0 (16)	O2'—C15'—H15B	105.1 (18)
C16—C15—H15A	106.4 (17)	C17'—C15'—H15B	106.1 (17)
C17—C15—H15A	109.5 (17)	C16'—C15'—H15B	115.1 (18)
C15—C16—H16A	109.5	C15'—C16'—H16D	109.5
C15—C16—H16B	109.5	C15'—C16'—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16'—H16E	109.5
C15—C16—H16C	109.5	C15'—C16'—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16'—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16'—H16F	109.5
C15—C17—H17A	109.5	C15'—C17'—H17D	109.5
C15—C17—H17B	109.5	C15'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
C15—C17—H17C	109.5	C15'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5

O3—P1—O1—C12	−10.2 (3)	O3'—P1'—O1'—C12'	10.5 (3)
O2—P1—O1—C12	115.2 (2)	O2'—P1'—O1'—C12'	−115.2 (2)
C11—P1—O1—C12	−137.9 (2)	C11'—P1'—O1'—C12'	138.3 (2)
O3—P1—O2—C15	53.5 (3)	O3'—P1'—O2'—C15'	−54.7 (3)
O1—P1—O2—C15	−71.1 (2)	O1'—P1'—O2'—C15'	70.4 (2)
C11—P1—O2—C15	−179.8 (2)	C11'—P1'—O2'—C15'	178.9 (2)
C9—C1—C2—O4	−177.3 (3)	C9'—C1'—C2'—O4'	177.3 (2)
C11—C1—C2—O4	6.2 (4)	C11'—C1'—C2'—O4'	−4.9 (4)
C9—C1—C2—C3	2.9 (4)	C9'—C1'—C2'—C3'	−2.3 (4)
C11—C1—C2—C3	−173.7 (3)	C11'—C1'—C2'—C3'	175.4 (3)
O4—C2—C3—C4	179.2 (3)	O4'—C2'—C3'—C4'	−179.8 (3)
C1—C2—C3—C4	−0.9 (5)	C1'—C2'—C3'—C4'	−0.2 (5)
C2—C3—C4—C10	−1.0 (6)	C2'—C3'—C4'—C10'	1.3 (5)
C10—C5—C6—C7	−0.5 (7)	C10'—C5'—C6'—C7'	0.8 (6)
C5—C6—C7—C8	1.2 (7)	C5'—C6'—C7'—C8'	−0.9 (6)
C6—C7—C8—C9	−0.4 (6)	C6'—C7'—C8'—C9'	−0.1 (6)
C7—C8—C9—C10	−1.0 (5)	C7'—C8'—C9'—C10'	1.0 (5)
C7—C8—C9—C1	179.5 (3)	C7'—C8'—C9'—C1'	−177.6 (3)
C2—C1—C9—C8	176.5 (3)	C2'—C1'—C9'—C8'	−177.9 (3)
C11—C1—C9—C8	−7.1 (4)	C11'—C1'—C9'—C8'	4.5 (4)
C2—C1—C9—C10	−2.9 (4)	C2'—C1'—C9'—C10'	3.6 (4)
C11—C1—C9—C10	173.5 (3)	C11'—C1'—C9'—C10'	−174.0 (3)
C3—C4—C10—C5	−179.3 (3)	C3'—C4'—C10'—C9'	0.1 (5)
C3—C4—C10—C9	0.9 (5)	C3'—C4'—C10'—C5'	180.0 (3)
C6—C5—C10—C4	179.1 (4)	C8'—C9'—C10'—C4'	178.9 (3)
C6—C5—C10—C9	−1.0 (6)	C1'—C9'—C10'—C4'	−2.5 (4)
C8—C9—C10—C4	−178.4 (3)	C8'—C9'—C10'—C5'	−1.1 (4)
C1—C9—C10—C4	1.1 (4)	C1'—C9'—C10'—C5'	177.6 (3)
C8—C9—C10—C5	1.7 (4)	C6'—C5'—C10'—C4'	−179.7 (4)
C1—C9—C10—C5	−178.8 (3)	C6'—C5'—C10'—C9'	0.2 (5)
C2—C1—C11—P1	88.2 (3)	C2'—C1'—C11'—P1'	−88.6 (3)
C9—C1—C11—P1	−88.3 (3)	C9'—C1'—C11'—P1'	89.0 (3)
O3—P1—C11—C1	−53.6 (3)	O3'—P1'—C11'—C1'	55.7 (3)
O2—P1—C11—C1	−178.6 (2)	O1'—P1'—C11'—C1'	−69.7 (3)
O1—P1—C11—C1	71.7 (3)	O2'—P1'—C11'—C1'	−179.4 (2)
P1—O1—C12—C14	−157.4 (2)	P1'—O1'—C12'—C14'	153.4 (2)
P1—O1—C12—C13	80.7 (3)	P1'—O1'—C12'—C13'	−83.6 (3)
P1—O2—C15—C16	110.5 (3)	P1'—O2'—C15'—C17'	119.7 (3)
P1—O2—C15—C17	−125.6 (3)	P1'—O2'—C15'—C16'	−116.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3′ⁱ	0.80 (4)	1.88 (4)	2.683 (3)	178 (4)
O4′—H4C···O3ⁱⁱ	0.89 (4)	1.80 (4)	2.669 (3)	166 (3)
C3′—H3B···O3ⁱⁱ	1.02 (3)	2.59 (3)	3.318 (5)	128 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃PO₄
M_r	322.32
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	9.166 (1), 22.484 (2), 9.579 (1)
β (°)	118.21 (1)
V (Å³)	1739.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.2 × 0.15 × 0.1

Data collection
Diffractometer	Xcalibur diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.966, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	10929, 6056, 4614
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.084, 1.00
No. of reflections	6056
No. of parameters	463
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21
Absolute structure	Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter	0.00 (8)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990), SHELXL9.

Selected geometric parameters (Å, º) top

C1—C2	1.366 (4)	C1'—C2'	1.385 (4)
C2—C3	1.418 (5)	C2'—C3'	1.403 (4)

C14—C12—C13	113.1 (3)	C14'—C12'—C13'	113.9 (3)

C9—C1—C2—O4	−177.3 (3)	C9'—C1'—C2'—O4'	177.3 (2)
C2—C1—C11—P1	88.2 (3)	C2'—C1'—C11'—P1'	−88.6 (3)
O2—P1—C11—C1	−178.6 (2)	O2'—P1'—C11'—C1'	−179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3'ⁱ	0.80 (4)	1.88 (4)	2.683 (3)	178 (4)
O4'—H4C···O3ⁱⁱ	0.89 (4)	1.80 (4)	2.669 (3)	166 (3)
C3'—H3B···O3ⁱⁱ	1.02 (3)	2.59 (3)	3.318 (5)	128 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1.

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