The typical crystal structures of a few representative α-aryl-α-hy­droxy­phospho­nates

The crystal structures of seven α-aryl-α-hy­droxy­phospho­nates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hy­droxy)(phenyl)m­eth­yl]phospho­nate, C₉H₁₃O₄P, dimethyl [(3,4-di­meth­oxy­phen­yl)(hy­droxy)­meth­yl]phospho­nate, C₁₁H₁₇O₆P, dimethyl (1-hy­droxy-1-phenyl­eth­yl)phospho­nate, C₁₀H₁₅O₄P, dimethyl [1-hy­droxy-1-(4-nitro­phen­yl)eth­yl]phospho­nate, C₁₀H₁₄NO₆P, dibenzyl [hy­droxy(2-nitro­phen­yl)meth­yl]phospho­nate, C₂₁H₂₀NO₆P, dibenzyl [(3-chloro­phen­yl)(hy­droxy)meth­yl]phospho­nate, C₂₁H₂₀ClO₄P, and dibenzyl [hy­droxy(4-methyl­phen­yl)meth­yl]phospho­nate, C₂₂H₂₃O₄P, were studied to gain a better understanding of the organization in this type of mol­ecule in the solid state. The crystals obtained for this series of compounds show a balance between C—OH...O=P chain-linked packing and the dimeric types of hydrogen-bond bridges of inter­molecular pairs of such functions. The description is based on primary graph-set descriptors. Using graph-set descriptors one level deeper (i.e. secondary graph sets of the C—H...O type) revealed a similarity in the graph-set descriptors, suggesting a fine inter­play of substituent- and shape-dependent effects on strong–weak inter­actions. It seems that the formation of chains or dimers is governed not only by the presence of a tertiary Cα atom, but also by the nature and crowding of the ortho substituents of the α-aryl group.

Computing details

For all structures, data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: PLATON (Spek, 2009).

Dibenzyl [hydroxy(4-methylphenyl)methyl]phosphonate (3c)

Crystal data

C22H23O4P	Dx = 1.318 Mg m^−3
Mr = 382.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4004 reflections
a = 16.7332 (8) Å	θ = 4.5–27.9°
b = 8.2012 (3) Å	µ = 0.17 mm^−1
c = 28.0902 (13) Å	T = 173 K
V = 3854.9 (3) Å^3	Block, colorless
Z = 8	0.37 × 0.15 × 0.05 mm
F(000) = 1616

Data collection

Agilent Xcalibur Sapphire3 diffractometer	4758 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3133 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.070
ω scans	θmax = 28.3°, θmin = 4.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −22→21
Tmin = 0.980, Tmax = 1.000	k = −10→10
29616 measured reflections	l = −36→37

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0669P)^2 + 1.3244P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4758 reflections	Δρmax = 0.45 e Å^−3
265 parameters	Δρmin = −0.26 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.86630 (3)	0.11650 (7)	0.74859 (2)	0.02500 (16)
O1	0.88249 (10)	0.28792 (18)	0.76026 (6)	0.0334 (4)
O2	0.83579 (9)	0.00874 (17)	0.79113 (5)	0.0314 (4)
O3	0.79822 (9)	0.09657 (16)	0.71029 (5)	0.0288 (4)
C5	1.02433 (14)	0.1749 (3)	0.58777 (8)	0.0340 (5)
O4	1.01055 (11)	0.0164 (2)	0.76139 (6)	0.0395 (4)
C10	0.71903 (14)	0.1766 (3)	0.64312 (9)	0.0332 (5)
C3	1.03925 (14)	0.1711 (3)	0.67304 (9)	0.0335 (5)
H3	1.0670 (8)	0.2088 (10)	0.7011 (8)	0.040*
C11	0.73182 (17)	0.1995 (3)	0.59491 (10)	0.0421 (6)
H11	0.7791 (15)	0.2462 (15)	0.5842 (4)	0.051*
C1	0.95057 (13)	−0.0002 (3)	0.72631 (8)	0.0285 (5)
H1	0.9350	−0.1175	0.7237	0.034*
C18	0.87025 (14)	0.1879 (3)	0.87877 (9)	0.0363 (5)
H18	0.9039 (10)	0.2212 (10)	0.8520 (8)	0.044*
C2	0.97640 (13)	0.0618 (2)	0.67771 (8)	0.0272 (5)
C7	0.93737 (14)	0.0092 (3)	0.63681 (8)	0.0303 (5)
H7	0.8948 (12)	−0.065 (2)	0.63923 (10)	0.036*
C4	1.06260 (15)	0.2263 (3)	0.62880 (9)	0.0369 (6)
H4	1.1080 (12)	0.305 (2)	0.62631 (11)	0.044*
C17	0.79922 (14)	0.1056 (3)	0.87028 (8)	0.0308 (5)
C19	0.89383 (17)	0.2232 (3)	0.92481 (9)	0.0398 (6)
H19	0.9437 (15)	0.2807 (17)	0.93039 (19)	0.048*
C6	0.96076 (14)	0.0661 (3)	0.59253 (8)	0.0339 (5)
H6	0.9318 (8)	0.0289 (10)	0.5637 (8)	0.041*
C22	0.75307 (15)	0.0584 (3)	0.90880 (9)	0.0366 (6)
H22	0.7036 (14)	−0.0020 (17)	0.90344 (18)	0.044*
C16	0.77049 (14)	0.0704 (3)	0.82078 (8)	0.0334 (5)
H16A	0.7267 (8)	−0.0121 (14)	0.82201 (8)	0.040*
H16B	0.7485 (4)	0.1722 (18)	0.8064 (3)	0.040*
C15	0.64759 (15)	0.1085 (3)	0.65822 (10)	0.0381 (6)
H15	0.6377 (3)	0.0941 (5)	0.6925 (10)	0.046*
C21	0.77629 (16)	0.0958 (3)	0.95484 (9)	0.0439 (6)
H21	0.7423 (10)	0.0644 (10)	0.9818 (8)	0.053*
C20	0.84685 (17)	0.1770 (3)	0.96282 (10)	0.0439 (6)
H20	0.8624 (6)	0.2000 (8)	0.9928 (10)	0.053*
C13	0.6045 (2)	0.0829 (3)	0.57840 (12)	0.0545 (8)
H13	0.5656 (14)	0.0496 (12)	0.5561 (8)	0.065*
C12	0.6739 (2)	0.1524 (4)	0.56281 (11)	0.0543 (8)
H12	0.6819 (4)	0.1678 (7)	0.5310 (12)	0.065*
C14	0.59054 (18)	0.0609 (3)	0.62603 (11)	0.0496 (7)
H14	0.5416 (16)	0.0130 (16)	0.6367 (4)	0.060*
C8	1.05096 (18)	0.2326 (3)	0.53963 (10)	0.0510 (7)
H8A	1.0775 (11)	0.332 (2)	0.54271 (13)	0.076*
H8B	1.0066 (8)	0.246 (2)	0.5200 (4)	0.076*
H8C	1.0853 (11)	0.1559 (17)	0.5263 (4)	0.076*
C9	0.78111 (16)	0.2317 (3)	0.67775 (9)	0.0365 (6)
H9A	0.8320 (9)	0.2650 (7)	0.6600 (3)	0.044*
H9B	0.7608 (4)	0.3304 (18)	0.6965 (3)	0.044*
H40	1.0494 (17)	−0.069 (3)	0.7537 (9)	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0241 (3)	0.0235 (3)	0.0274 (3)	0.0000 (2)	−0.0007 (2)	−0.0014 (2)
O1	0.0343 (10)	0.0261 (8)	0.0398 (10)	−0.0042 (6)	−0.0002 (7)	−0.0049 (6)
O2	0.0307 (9)	0.0317 (8)	0.0318 (9)	0.0046 (7)	0.0043 (7)	0.0026 (6)
O3	0.0263 (8)	0.0233 (7)	0.0368 (9)	−0.0008 (6)	−0.0052 (6)	0.0032 (6)
C5	0.0316 (13)	0.0319 (12)	0.0385 (14)	0.0058 (10)	0.0097 (10)	0.0033 (10)
O4	0.0338 (10)	0.0462 (10)	0.0385 (10)	0.0099 (8)	−0.0069 (7)	−0.0040 (7)
C10	0.0333 (14)	0.0245 (11)	0.0417 (14)	0.0078 (9)	−0.0096 (10)	0.0001 (9)
C3	0.0285 (13)	0.0348 (12)	0.0371 (13)	−0.0001 (9)	−0.0003 (10)	−0.0092 (10)
C11	0.0348 (15)	0.0412 (14)	0.0503 (17)	0.0066 (11)	0.0032 (12)	0.0078 (11)
C1	0.0293 (12)	0.0288 (11)	0.0274 (12)	0.0041 (9)	−0.0030 (9)	−0.0032 (8)
C18	0.0315 (14)	0.0395 (13)	0.0379 (14)	0.0007 (10)	0.0035 (10)	0.0022 (10)
C2	0.0273 (12)	0.0253 (10)	0.0291 (12)	0.0046 (9)	0.0008 (9)	−0.0027 (8)
C7	0.0295 (13)	0.0295 (11)	0.0320 (12)	−0.0046 (9)	0.0000 (9)	−0.0016 (9)
C4	0.0314 (14)	0.0321 (12)	0.0472 (15)	−0.0043 (10)	0.0073 (11)	−0.0036 (10)
C17	0.0264 (12)	0.0300 (11)	0.0359 (13)	0.0063 (9)	0.0029 (9)	0.0002 (9)
C19	0.0376 (15)	0.0400 (14)	0.0417 (15)	0.0007 (11)	−0.0044 (11)	0.0001 (11)
C6	0.0356 (14)	0.0360 (12)	0.0302 (13)	0.0009 (10)	−0.0026 (10)	−0.0040 (9)
C22	0.0312 (14)	0.0390 (13)	0.0395 (15)	0.0023 (10)	0.0060 (10)	0.0030 (10)
C16	0.0274 (13)	0.0374 (12)	0.0355 (13)	0.0003 (10)	0.0059 (9)	0.0000 (10)
C15	0.0391 (15)	0.0325 (13)	0.0428 (15)	0.0028 (10)	0.0006 (11)	0.0084 (10)
C21	0.0387 (15)	0.0571 (17)	0.0358 (14)	0.0085 (12)	0.0103 (11)	0.0075 (11)
C20	0.0468 (17)	0.0520 (15)	0.0331 (14)	0.0113 (13)	−0.0048 (12)	−0.0001 (11)
C13	0.0544 (19)	0.0442 (16)	0.065 (2)	0.0061 (14)	−0.0302 (16)	−0.0060 (14)
C12	0.069 (2)	0.0599 (18)	0.0341 (15)	0.0163 (16)	−0.0069 (14)	0.0032 (12)
C14	0.0355 (16)	0.0376 (14)	0.076 (2)	−0.0033 (11)	−0.0111 (14)	0.0075 (13)
C8	0.0470 (17)	0.0616 (18)	0.0443 (17)	0.0012 (14)	0.0132 (13)	0.0092 (13)
C9	0.0404 (15)	0.0244 (11)	0.0447 (14)	0.0007 (10)	−0.0088 (11)	0.0073 (10)

Geometric parameters (Å, º)

P1—O1	1.4687 (16)	C7—H7	0.94 (3)
P1—O2	1.5716 (16)	C4—H4	1.00 (3)
P1—O3	1.5754 (15)	C17—C22	1.385 (3)
P1—C1	1.815 (2)	C17—C16	1.499 (3)
O2—C16	1.464 (3)	C19—C20	1.379 (4)
O3—C9	1.465 (3)	C19—H19	0.97 (3)
C5—C4	1.384 (3)	C6—H6	0.99 (3)
C5—C6	1.395 (3)	C22—C21	1.385 (4)
C5—C8	1.501 (3)	C22—H22	0.98 (3)
O4—C1	1.413 (3)	C16—H16A	0.998 (17)
O4—H40	0.98 (3)	C16—H16B	0.998 (17)
C10—C11	1.384 (4)	C15—C14	1.372 (4)
C10—C15	1.386 (3)	C15—H15	0.98 (3)
C10—C9	1.493 (3)	C21—C20	1.374 (4)
C3—C4	1.379 (3)	C21—H21	0.98 (3)
C3—C2	1.388 (3)	C20—H20	0.90 (3)
C3—H3	0.97 (3)	C13—C12	1.365 (4)
C11—C12	1.379 (4)	C13—C14	1.370 (4)
C11—H11	0.93 (3)	C13—H13	0.94 (3)
C1—C2	1.520 (3)	C12—H12	0.91 (3)
C1—H1	1.0000	C14—H14	0.96 (3)
C18—C19	1.383 (4)	C8—H8A	0.930 (16)
C18—C17	1.388 (3)	C8—H8B	0.930 (15)
C18—H18	0.98 (3)	C8—H8C	0.930 (15)
C2—C7	1.390 (3)	C9—H9A	1.024 (18)
C7—C6	1.385 (3)	C9—H9B	1.024 (18)
O1—P1—O2	115.37 (9)	C18—C19—H19	119.9
O1—P1—O3	112.66 (9)	C7—C6—C5	121.1 (2)
O2—P1—O3	103.06 (8)	C7—C6—H6	119.4
O1—P1—C1	115.99 (10)	C5—C6—H6	119.4
O2—P1—C1	102.59 (9)	C17—C22—C21	120.8 (2)
O3—P1—C1	105.77 (9)	C17—C22—H22	119.6
C16—O2—P1	118.73 (13)	C21—C22—H22	119.6
C9—O3—P1	119.27 (13)	O2—C16—C17	110.78 (19)
C4—C5—C6	117.9 (2)	O2—C16—H16A	109.5
C4—C5—C8	121.1 (2)	C17—C16—H16A	109.5
C6—C5—C8	121.0 (2)	O2—C16—H16B	109.5
C1—O4—H40	104.4 (15)	C17—C16—H16B	109.5
C11—C10—C15	119.2 (2)	H16A—C16—H16B	108.1
C11—C10—C9	119.3 (2)	C14—C15—C10	120.9 (3)
C15—C10—C9	121.5 (2)	C14—C15—H15	119.6
C4—C3—C2	120.8 (2)	C10—C15—H15	119.6
C4—C3—H3	119.6	C20—C21—C22	120.0 (2)
C2—C3—H3	119.6	C20—C21—H21	120.0
C12—C11—C10	119.6 (3)	C22—C21—H21	120.0
C12—C11—H11	120.2	C21—C20—C19	119.8 (3)
C10—C11—H11	120.2	C21—C20—H20	120.1
O4—C1—C2	113.10 (19)	C19—C20—H20	120.1
O4—C1—P1	105.11 (14)	C12—C13—C14	120.9 (3)
C2—C1—P1	110.74 (14)	C12—C13—H13	119.6
O4—C1—H1	109.3	C14—C13—H13	119.6
C2—C1—H1	109.3	C13—C12—C11	120.3 (3)
P1—C1—H1	109.3	C13—C12—H12	119.8
C19—C18—C17	120.5 (2)	C11—C12—H12	119.8
C19—C18—H18	119.8	C13—C14—C15	119.2 (3)
C17—C18—H18	119.8	C13—C14—H14	120.4
C3—C2—C7	118.6 (2)	C15—C14—H14	120.4
C3—C2—C1	121.1 (2)	C5—C8—H8A	109.5
C7—C2—C1	120.3 (2)	C5—C8—H8B	109.5
C6—C7—C2	120.3 (2)	H8A—C8—H8B	109.5
C6—C7—H7	119.8	C5—C8—H8C	109.5
C2—C7—H7	119.8	H8A—C8—H8C	109.5
C3—C4—C5	121.2 (2)	H8B—C8—H8C	109.5
C3—C4—H4	119.4	O3—C9—C10	108.29 (18)
C5—C4—H4	119.4	O3—C9—H9A	110.0
C22—C17—C18	118.6 (2)	C10—C9—H9A	110.0
C22—C17—C16	119.5 (2)	O3—C9—H9B	110.0
C18—C17—C16	121.9 (2)	C10—C9—H9B	110.0
C20—C19—C18	120.3 (3)	H9A—C9—H9B	108.4
C20—C19—H19	119.9
O1—P1—O2—C16	48.40 (18)	C8—C5—C4—C3	−178.7 (2)
O3—P1—O2—C16	−74.80 (17)	C19—C18—C17—C22	−0.6 (3)
C1—P1—O2—C16	175.47 (16)	C19—C18—C17—C16	177.9 (2)
O1—P1—O3—C9	23.70 (19)	C17—C18—C19—C20	−0.1 (4)
O2—P1—O3—C9	148.69 (16)	C2—C7—C6—C5	1.0 (3)
C1—P1—O3—C9	−103.97 (17)	C4—C5—C6—C7	−1.0 (3)
C15—C10—C11—C12	−0.8 (4)	C8—C5—C6—C7	178.3 (2)
C9—C10—C11—C12	−178.4 (2)	C18—C17—C22—C21	1.5 (3)
O1—P1—C1—O4	55.39 (17)	C16—C17—C22—C21	−177.0 (2)
O2—P1—C1—O4	−71.29 (16)	P1—O2—C16—C17	−113.16 (18)
O3—P1—C1—O4	−178.96 (13)	C22—C17—C16—O2	−136.4 (2)
O1—P1—C1—C2	−67.08 (17)	C18—C17—C16—O2	45.1 (3)
O2—P1—C1—C2	166.25 (15)	C11—C10—C15—C14	1.3 (4)
O3—P1—C1—C2	58.57 (17)	C9—C10—C15—C14	178.9 (2)
C4—C3—C2—C7	0.0 (3)	C17—C22—C21—C20	−1.7 (4)
C4—C3—C2—C1	179.7 (2)	C22—C21—C20—C19	1.0 (4)
O4—C1—C2—C3	−20.6 (3)	C18—C19—C20—C21	−0.1 (4)
P1—C1—C2—C3	97.0 (2)	C14—C13—C12—C11	1.0 (4)
O4—C1—C2—C7	159.11 (19)	C10—C11—C12—C13	−0.4 (4)
P1—C1—C2—C7	−83.2 (2)	C12—C13—C14—C15	−0.5 (4)
C3—C2—C7—C6	−0.4 (3)	C10—C15—C14—C13	−0.7 (4)
C1—C2—C7—C6	179.8 (2)	P1—O3—C9—C10	175.76 (15)
C2—C3—C4—C5	0.0 (4)	C11—C10—C9—O3	−129.7 (2)
C6—C5—C4—C3	0.5 (3)	C15—C10—C9—O3	52.6 (3)

Dibenzyl [(3-chlorophenyl)(hydroxy)methyl]phosphonate (3b)

Crystal data

C21H20ClO4P	F(000) = 420
Mr = 402.79	Dx = 1.393 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.4239 (8) Å	Cell parameters from 2191 reflections
b = 7.8757 (5) Å	θ = 4.4–25.4°
c = 12.0461 (7) Å	µ = 0.31 mm^−1
β = 103.775 (7)°	T = 133 K
V = 960.49 (11) Å^3	Block, colorless
Z = 2	0.30 × 0.22 × 0.20 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	3407 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2955 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.028
ω scans	θmax = 26.4°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −9→13
Tmin = 0.991, Tmax = 1.000	k = −8→9
6934 measured reflections	l = −15→15

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.2038P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.34 e Å^−3
3407 reflections	Δρmin = −0.20 e Å^−3
255 parameters	Absolute structure: Refined as an inversion twin
1 restraint	Absolute structure parameter: 0.35 (12)

Special details

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. Refined as a 2-component inversion twin

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.39196 (10)	0.20951 (14)	0.13606 (8)	0.0314 (3)
Cl1	0.87251 (14)	0.3666 (2)	0.47865 (10)	0.0640 (4)
O2	0.4032 (3)	0.2610 (4)	0.2646 (2)	0.0368 (7)
O4	0.5090 (3)	0.2690 (5)	−0.0254 (2)	0.0483 (9)
H4	0.5506	0.3370	−0.0576	0.072*
O1	0.3842 (3)	0.0246 (4)	0.1175 (2)	0.0404 (7)
O3	0.2705 (3)	0.3148 (4)	0.0693 (3)	0.0458 (8)
C2	0.6585 (4)	0.2610 (5)	0.1657 (3)	0.0315 (9)
C3	0.7023 (4)	0.3308 (6)	0.2740 (4)	0.0357 (9)
H3	0.652 (3)	0.410 (5)	0.2999 (15)	0.043*
C9	0.4049 (4)	0.2024 (6)	0.4615 (3)	0.0366 (9)
C4	0.8229 (4)	0.2798 (7)	0.3431 (4)	0.0405 (10)
C5	0.9030 (5)	0.1650 (6)	0.3042 (4)	0.0444 (12)
H5	0.986 (5)	0.1341 (18)	0.350 (3)	0.053*
C14	0.2867 (4)	0.2884 (7)	0.4557 (4)	0.0464 (11)
H14	0.2292	0.3133	0.3837	0.056*
C21	−0.0793 (4)	0.2817 (6)	−0.0668 (4)	0.0407 (10)
H21	−0.1135 (18)	0.337 (3)	−0.011 (3)	0.049*
C20	−0.1603 (5)	0.2497 (7)	−0.1726 (4)	0.0483 (12)
H20	−0.245 (5)	0.2777 (18)	−0.1868 (9)	0.058*
C13	0.2537 (5)	0.3374 (7)	0.5567 (5)	0.0565 (14)
H13	0.1733	0.3965	0.5528	0.068*
C10	0.4860 (5)	0.1684 (6)	0.5690 (4)	0.0409 (11)
H10	0.5671	0.1100	0.5752	0.049*
C17	0.1022 (5)	0.1597 (6)	−0.1257 (4)	0.0397 (11)
H17	0.192 (5)	0.1288 (17)	−0.1098 (9)	0.048*
C1	0.5270 (4)	0.3155 (6)	0.0922 (3)	0.0363 (10)
H1	0.5172	0.4412	0.0983	0.044*
C16	0.0516 (4)	0.2340 (6)	−0.0423 (3)	0.0364 (10)
C11	0.4485 (5)	0.2199 (7)	0.6674 (4)	0.0502 (12)
H11	0.5044	0.1964	0.7404	0.060*
C18	0.0214 (5)	0.1302 (7)	−0.2335 (4)	0.0481 (12)
H18	0.058 (2)	0.079 (3)	−0.292 (3)	0.058*
C8	0.4424 (5)	0.1376 (6)	0.3573 (4)	0.0460 (11)
H8A	0.548 (4)	0.1175 (10)	0.3753 (7)	0.055*
H8B	0.3941 (17)	0.018 (4)	0.3320 (9)	0.055*
C15	0.1368 (4)	0.2643 (7)	0.0766 (4)	0.0454 (12)
H15A	0.0933 (15)	0.364 (3)	0.1186 (15)	0.054*
H15B	0.1420 (4)	0.149 (4)	0.1272 (18)	0.054*
C7	0.7381 (4)	0.1431 (6)	0.1276 (4)	0.0419 (10)
H7	0.7094	0.0942	0.0538	0.050*
C19	−0.1103 (5)	0.1741 (7)	−0.2565 (4)	0.0494 (13)
H19	−0.164 (3)	0.1531 (14)	−0.327 (4)	0.059*
C6	0.8590 (5)	0.0974 (6)	0.1974 (4)	0.0470 (12)
H6	0.918 (3)	0.009 (5)	0.1677 (16)	0.056*
C12	0.3337 (6)	0.3025 (8)	0.6596 (5)	0.0594 (15)
H12	0.3088	0.3365	0.7272	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0336 (5)	0.0304 (6)	0.0304 (5)	−0.0026 (4)	0.0082 (4)	0.0004 (4)
Cl1	0.0613 (8)	0.0802 (11)	0.0410 (6)	−0.0028 (7)	−0.0065 (5)	−0.0050 (6)
O2	0.0463 (17)	0.0322 (17)	0.0348 (14)	0.0037 (12)	0.0154 (12)	0.0014 (12)
O4	0.060 (2)	0.056 (2)	0.0313 (15)	−0.0126 (16)	0.0151 (14)	−0.0007 (14)
O1	0.0498 (19)	0.0327 (18)	0.0408 (16)	−0.0045 (14)	0.0149 (14)	−0.0031 (13)
O3	0.0353 (16)	0.047 (2)	0.0509 (17)	−0.0045 (14)	0.0029 (13)	0.0120 (15)
C2	0.030 (2)	0.031 (2)	0.0358 (19)	−0.0061 (16)	0.0123 (16)	0.0046 (16)
C3	0.032 (2)	0.030 (2)	0.046 (2)	−0.0003 (17)	0.0084 (18)	0.0003 (18)
C9	0.046 (2)	0.030 (2)	0.038 (2)	−0.010 (2)	0.0198 (18)	−0.005 (2)
C4	0.039 (2)	0.041 (3)	0.039 (2)	−0.0078 (19)	0.0048 (18)	0.0057 (19)
C5	0.034 (2)	0.032 (3)	0.067 (3)	−0.0012 (18)	0.012 (2)	0.011 (2)
C14	0.043 (3)	0.042 (3)	0.053 (3)	0.000 (2)	0.008 (2)	−0.002 (2)
C21	0.041 (2)	0.035 (3)	0.051 (3)	0.0006 (19)	0.020 (2)	0.003 (2)
C20	0.036 (2)	0.047 (3)	0.059 (3)	0.002 (2)	0.007 (2)	0.005 (2)
C13	0.049 (3)	0.045 (3)	0.086 (4)	−0.008 (2)	0.038 (3)	−0.015 (3)
C10	0.042 (2)	0.033 (3)	0.048 (2)	−0.0031 (18)	0.0109 (19)	0.0041 (18)
C17	0.039 (2)	0.042 (3)	0.039 (2)	0.0072 (19)	0.0093 (18)	0.0051 (18)
C1	0.039 (2)	0.037 (3)	0.033 (2)	−0.0066 (19)	0.0087 (17)	0.0011 (17)
C16	0.033 (2)	0.036 (3)	0.041 (2)	−0.0009 (18)	0.0114 (17)	0.0069 (19)
C11	0.072 (3)	0.042 (3)	0.038 (2)	−0.021 (3)	0.014 (2)	−0.005 (2)
C18	0.060 (3)	0.042 (3)	0.045 (2)	0.002 (2)	0.019 (2)	−0.005 (2)
C8	0.063 (3)	0.037 (3)	0.043 (2)	0.014 (2)	0.022 (2)	0.010 (2)
C15	0.036 (2)	0.059 (3)	0.045 (2)	−0.002 (2)	0.0163 (19)	0.001 (2)
C7	0.044 (3)	0.038 (3)	0.048 (2)	−0.007 (2)	0.019 (2)	−0.0059 (19)
C19	0.055 (3)	0.047 (3)	0.039 (2)	−0.006 (2)	−0.003 (2)	0.001 (2)
C6	0.043 (3)	0.034 (3)	0.070 (3)	0.001 (2)	0.026 (2)	−0.001 (2)
C12	0.080 (4)	0.055 (4)	0.055 (3)	−0.022 (3)	0.038 (3)	−0.022 (3)

Geometric parameters (Å, º)

P1—O1	1.473 (3)	C20—C19	1.378 (7)
P1—O3	1.566 (3)	C20—H20	0.88 (5)
P1—O2	1.578 (3)	C13—C12	1.347 (8)
P1—C1	1.819 (4)	C13—H13	0.9500
Cl1—C4	1.732 (5)	C10—C11	1.394 (6)
O2—C8	1.463 (5)	C10—H10	0.9500
O4—C1	1.432 (5)	C17—C16	1.372 (6)
O4—H4	0.8400	C17—C18	1.389 (6)
O3—C15	1.472 (5)	C17—H17	0.94 (5)
C2—C3	1.389 (6)	C1—H1	1.0000
C2—C7	1.394 (6)	C16—C15	1.514 (6)
C2—C1	1.506 (6)	C11—C12	1.346 (8)
C3—C4	1.391 (6)	C11—H11	0.9500
C3—H3	0.92 (5)	C18—C19	1.379 (7)
C9—C14	1.393 (6)	C18—H18	0.97 (5)
C9—C10	1.393 (6)	C8—H8A	1.08 (4)
C9—C8	1.492 (6)	C8—H8B	1.08 (4)
C4—C5	1.386 (7)	C15—H15A	1.09 (4)
C5—C6	1.367 (7)	C15—H15B	1.09 (4)
C5—H5	0.94 (5)	C7—C6	1.386 (7)
C14—C13	1.395 (7)	C7—H7	0.9500
C14—H14	0.9500	C19—H19	0.92 (5)
C21—C20	1.374 (7)	C6—H6	1.04 (5)
C21—C16	1.377 (6)	C12—H12	0.9500
C21—H21	0.94 (5)
O1—P1—O3	115.92 (18)	C18—C17—H17	119.9
O1—P1—O2	113.06 (17)	O4—C1—C2	113.3 (3)
O3—P1—O2	103.29 (17)	O4—C1—P1	104.0 (3)
O1—P1—C1	115.33 (19)	C2—C1—P1	110.9 (3)
O3—P1—C1	101.24 (19)	O4—C1—H1	109.5
O2—P1—C1	106.57 (18)	C2—C1—H1	109.5
C8—O2—P1	121.3 (3)	P1—C1—H1	109.5
C1—O4—H4	109.5	C17—C16—C21	119.6 (4)
C15—O3—P1	119.2 (3)	C17—C16—C15	121.2 (4)
C3—C2—C7	119.0 (4)	C21—C16—C15	119.2 (4)
C3—C2—C1	119.3 (4)	C12—C11—C10	120.4 (5)
C7—C2—C1	121.7 (4)	C12—C11—H11	119.8
C2—C3—C4	119.7 (4)	C10—C11—H11	119.8
C2—C3—H3	120.2	C19—C18—C17	119.9 (5)
C4—C3—H3	120.2	C19—C18—H18	120.0
C14—C9—C10	118.3 (4)	C17—C18—H18	120.0
C14—C9—C8	122.0 (4)	O2—C8—C9	109.5 (4)
C10—C9—C8	119.6 (4)	O2—C8—H8A	109.8
C5—C4—C3	121.2 (4)	C9—C8—H8A	109.8
C5—C4—Cl1	120.5 (4)	O2—C8—H8B	109.8
C3—C4—Cl1	118.3 (4)	C9—C8—H8B	109.8
C6—C5—C4	118.6 (5)	H8A—C8—H8B	108.2
C6—C5—H5	120.7	O3—C15—C16	109.7 (3)
C4—C5—H5	120.7	O3—C15—H15A	109.7
C9—C14—C13	119.3 (5)	C16—C15—H15A	109.7
C9—C14—H14	120.3	O3—C15—H15B	109.7
C13—C14—H14	120.3	C16—C15—H15B	109.7
C20—C21—C16	120.5 (4)	H15A—C15—H15B	108.2
C20—C21—H21	119.8	C6—C7—C2	120.0 (4)
C16—C21—H21	119.8	C6—C7—H7	120.0
C21—C20—C19	120.3 (4)	C2—C7—H7	120.0
C21—C20—H20	119.9	C20—C19—C18	119.5 (4)
C19—C20—H20	119.9	C20—C19—H19	120.2
C12—C13—C14	121.2 (5)	C18—C19—H19	120.2
C12—C13—H13	119.4	C5—C6—C7	121.5 (4)
C14—C13—H13	119.4	C5—C6—H6	119.2
C9—C10—C11	120.3 (5)	C7—C6—H6	119.2
C9—C10—H10	119.9	C11—C12—C13	120.5 (5)
C11—C10—H10	119.9	C11—C12—H12	119.7
C16—C17—C18	120.2 (4)	C13—C12—H12	119.7
C16—C17—H17	119.9
O1—P1—O2—C8	17.5 (4)	O2—P1—C1—O4	−178.1 (3)
O3—P1—O2—C8	143.6 (3)	O1—P1—C1—C2	−66.5 (3)
C1—P1—O2—C8	−110.2 (3)	O3—P1—C1—C2	167.5 (3)
O1—P1—O3—C15	51.4 (4)	O2—P1—C1—C2	59.8 (3)
O2—P1—O3—C15	−72.8 (3)	C18—C17—C16—C21	−1.1 (7)
C1—P1—O3—C15	177.0 (3)	C18—C17—C16—C15	178.7 (4)
C7—C2—C3—C4	−1.3 (6)	C20—C21—C16—C17	2.4 (7)
C1—C2—C3—C4	179.3 (4)	C20—C21—C16—C15	−177.4 (5)
C2—C3—C4—C5	2.5 (6)	C9—C10—C11—C12	0.1 (7)
C2—C3—C4—Cl1	−178.7 (3)	C16—C17—C18—C19	−0.7 (7)
C3—C4—C5—C6	−2.3 (7)	P1—O2—C8—C9	−162.5 (3)
Cl1—C4—C5—C6	178.9 (3)	C14—C9—C8—O2	39.0 (6)
C10—C9—C14—C13	0.1 (7)	C10—C9—C8—O2	−144.8 (4)
C8—C9—C14—C13	176.4 (5)	P1—O3—C15—C16	−124.0 (4)
C16—C21—C20—C19	−2.0 (7)	C17—C16—C15—O3	37.6 (6)
C9—C14—C13—C12	−0.3 (8)	C21—C16—C15—O3	−142.6 (4)
C14—C9—C10—C11	0.0 (7)	C3—C2—C7—C6	−0.1 (6)
C8—C9—C10—C11	−176.4 (4)	C1—C2—C7—C6	179.4 (4)
C3—C2—C1—O4	164.9 (4)	C21—C20—C19—C18	0.2 (8)
C7—C2—C1—O4	−14.5 (6)	C17—C18—C19—C20	1.1 (8)
C3—C2—C1—P1	−78.6 (4)	C4—C5—C6—C7	0.9 (7)
C7—C2—C1—P1	102.0 (4)	C2—C7—C6—C5	0.2 (7)
O1—P1—C1—O4	55.6 (3)	C10—C11—C12—C13	−0.3 (8)
O3—P1—C1—O4	−70.4 (3)	C14—C13—C12—C11	0.4 (8)

Dibenzyl [hydroxy(2-nitrophenyl)methyl]phosphonate (3a)

Crystal data

C21H20NO6P	Z = 4
Mr = 413.35	F(000) = 864
Triclinic, P1	Dx = 1.390 Mg m^−3
a = 10.0795 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.8530 (6) Å	Cell parameters from 8023 reflections
c = 15.9354 (5) Å	θ = 4.2–31.4°
α = 111.110 (4)°	µ = 0.18 mm^−1
β = 90.852 (3)°	T = 133 K
γ = 106.326 (3)°	Block, colorless
V = 1975.23 (13) Å^3	0.43 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	11989 independent reflections
Radiation source: Enhance (Mo) X-ray Source	8512 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.038
ω scans	θmax = 30.5°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −14→14
Tmin = 0.980, Tmax = 1.000	k = −19→19
39828 measured reflections	l = −22→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.5554P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
11989 reflections	Δρmax = 0.60 e Å^−3
565 parameters	Δρmin = −0.30 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.34036 (4)	0.33610 (3)	0.24334 (2)	0.01798 (9)
H400	0.484 (2)	0.5613 (17)	0.3690 (13)	0.033 (5)*
P2	0.65755 (4)	0.70132 (3)	0.27149 (2)	0.01823 (9)
H100	0.496 (2)	0.4733 (18)	0.1433 (14)	0.049 (6)*
O9	0.81171 (10)	0.77607 (8)	0.30493 (7)	0.0215 (2)
O2	0.19137 (10)	0.25153 (8)	0.20799 (7)	0.0211 (2)
O8	0.59353 (10)	0.76486 (8)	0.22569 (7)	0.0227 (2)
O4	0.44813 (11)	0.50956 (9)	0.38479 (7)	0.0235 (2)
O3	0.41292 (10)	0.28115 (9)	0.29324 (8)	0.0236 (2)
C23	0.78247 (15)	0.60271 (11)	0.11945 (10)	0.0191 (3)
O10	0.53685 (11)	0.53214 (9)	0.12951 (7)	0.0246 (2)
O7	0.57636 (11)	0.67567 (9)	0.34107 (7)	0.0258 (2)
N1	−0.00314 (13)	0.38299 (11)	0.28147 (9)	0.0257 (3)
O5	0.06966 (12)	0.42184 (10)	0.23397 (8)	0.0307 (3)
C22	0.67239 (15)	0.58044 (11)	0.18032 (10)	0.0194 (3)
H22	0.6919 (4)	0.5306 (9)	0.2066 (5)	0.023*
N2	0.98969 (14)	0.62531 (11)	0.22338 (9)	0.0252 (3)
C24	0.92640 (15)	0.62283 (12)	0.13842 (10)	0.0212 (3)
C7	0.25435 (16)	0.42323 (12)	0.47355 (10)	0.0229 (3)
H7	0.3525 (19)	0.4450 (4)	0.4915 (4)	0.027*
C1	0.31458 (14)	0.45437 (11)	0.33225 (9)	0.0183 (3)
H1	0.2883 (5)	0.5001 (8)	0.3057 (5)	0.022*
C16	0.03692 (16)	0.07050 (12)	0.12503 (10)	0.0239 (3)
C2	0.20635 (14)	0.42283 (11)	0.39074 (9)	0.0184 (3)
C37	0.40708 (15)	0.77098 (13)	0.13515 (11)	0.0247 (3)
O1	0.41947 (11)	0.36438 (9)	0.17393 (7)	0.0252 (2)
C4	−0.03052 (17)	0.35731 (14)	0.42395 (11)	0.0271 (3)
H4	−0.126 (2)	0.3347 (5)	0.4066 (4)	0.033*
C10	0.59503 (17)	0.26396 (14)	0.44355 (12)	0.0303 (4)
H10	0.5792 (4)	0.3293 (14)	0.4789 (8)	0.036*
C3	0.06145 (15)	0.38843 (12)	0.36733 (10)	0.0207 (3)
C9	0.59567 (15)	0.23593 (13)	0.35077 (11)	0.0247 (3)
O11	0.91432 (13)	0.58963 (11)	0.27171 (8)	0.0348 (3)
O12	1.11618 (13)	0.66325 (12)	0.24296 (9)	0.0416 (3)
C17	−0.08745 (17)	0.08349 (13)	0.10044 (11)	0.0281 (3)
H17	−0.08650 (17)	0.1468 (13)	0.0867 (3)	0.034*
C25	1.01936 (17)	0.64088 (13)	0.07796 (11)	0.0275 (3)
H25	1.116 (2)	0.6549 (3)	0.0933 (3)	0.033*
C28	0.73746 (17)	0.60301 (12)	0.03646 (10)	0.0235 (3)
H28	0.6423 (19)	0.5915 (3)	0.0215 (3)	0.028*
C36	0.44344 (16)	0.74987 (15)	0.21718 (12)	0.0296 (4)
H36A	0.4195 (4)	0.8019 (7)	0.2729 (7)	0.036*
H36B	0.3898 (7)	0.6737 (10)	0.20999 (14)	0.036*
C14	0.62044 (16)	0.13931 (13)	0.29942 (11)	0.0278 (3)
H14	0.62187 (17)	0.1196 (4)	0.2354 (13)	0.033*
C31	1.00525 (19)	1.04519 (13)	0.37666 (11)	0.0303 (4)
H31	0.9248 (17)	1.0712 (6)	0.37619 (11)	0.036*
C8	0.56506 (16)	0.30702 (14)	0.30601 (13)	0.0307 (4)
H8A	0.6094 (6)	0.3856 (10)	0.3453 (5)	0.037*
H8B	0.6020 (5)	0.2920 (2)	0.2461 (8)	0.037*
C21	0.03337 (19)	−0.01984 (14)	0.14458 (11)	0.0311 (4)
H21	0.1159 (19)	−0.0290 (2)	0.1615 (4)	0.037*
C30	0.98821 (15)	0.94508 (12)	0.38278 (10)	0.0229 (3)
C26	0.97016 (18)	0.63830 (14)	−0.00458 (11)	0.0305 (4)
H26	1.0352 (13)	0.6495 (3)	−0.0487 (9)	0.037*
C35	1.10341 (17)	0.90917 (14)	0.38432 (11)	0.0292 (3)
H35	1.0927 (3)	0.8399 (15)	0.38963 (16)	0.035*
C29	0.84652 (17)	0.87533 (13)	0.38640 (11)	0.0305 (4)
H29A	0.84691 (17)	0.8581 (3)	0.4398 (8)	0.037*
H29B	0.7788 (10)	0.9130 (5)	0.38844 (12)	0.037*
C19	−0.21548 (19)	−0.08318 (14)	0.11459 (11)	0.0327 (4)
H19	−0.3023 (19)	−0.1358 (11)	0.11095 (14)	0.039*
C42	0.39673 (17)	0.69247 (14)	0.04910 (12)	0.0288 (3)
H42	0.4117 (3)	0.6234 (14)	0.04279 (17)	0.035*
O6	−0.12840 (13)	0.33932 (14)	0.26055 (10)	0.0544 (4)
C6	0.16325 (17)	0.39282 (14)	0.53056 (11)	0.0276 (3)
H6	0.1977 (8)	0.39435 (14)	0.5845 (12)	0.033*
C18	−0.21298 (18)	0.00679 (14)	0.09529 (12)	0.0321 (4)
H18	−0.3014 (19)	0.0165 (3)	0.0777 (4)	0.038*
C11	0.61763 (19)	0.19606 (16)	0.48406 (13)	0.0372 (4)
H11	0.61670 (19)	0.2154 (5)	0.5471 (14)	0.045*
C27	0.82926 (18)	0.61991 (14)	−0.02487 (11)	0.0286 (3)
H27	0.7955 (7)	0.61882 (14)	−0.0800 (12)	0.034*
C20	−0.0929 (2)	−0.09669 (14)	0.13900 (12)	0.0355 (4)
H20	−0.0943 (2)	−0.1560 (14)	0.1515 (3)	0.043*
C5	0.02075 (18)	0.36026 (14)	0.50618 (11)	0.0304 (4)
H5	−0.0428 (13)	0.3397 (4)	0.5464 (8)	0.036*
C38	0.38634 (18)	0.86858 (15)	0.14305 (12)	0.0330 (4)
H38	0.3931 (2)	0.9250 (12)	0.2036 (13)	0.040*
C15	0.17277 (18)	0.15174 (14)	0.12808 (12)	0.0358 (4)
H15A	0.2467 (11)	0.1232 (4)	0.13115 (12)	0.043*
H15B	0.17338 (19)	0.1671 (3)	0.0749 (8)	0.043*
C41	0.36579 (19)	0.71037 (16)	−0.02724 (12)	0.0358 (4)
H41	0.3578 (3)	0.6543 (12)	−0.0872 (13)	0.043*
C34	1.23371 (19)	0.97247 (17)	0.37825 (12)	0.0382 (4)
H34	1.3155 (18)	0.9466 (6)	0.37877 (12)	0.046*
C13	0.64307 (19)	0.07126 (15)	0.33998 (12)	0.0337 (4)
H13	0.6594 (4)	0.0058 (15)	0.3047 (8)	0.040*
C33	1.2494 (2)	1.07134 (17)	0.37148 (12)	0.0412 (5)
H33	1.337 (2)	1.1134 (10)	0.36705 (16)	0.049*
C12	0.64167 (19)	0.09951 (17)	0.43228 (13)	0.0368 (4)
H12	0.6571 (4)	0.0532 (11)	0.4601 (7)	0.044*
C39	0.3561 (2)	0.88701 (17)	0.06609 (13)	0.0415 (5)
H39	0.3421 (4)	0.9554 (16)	0.0719 (2)	0.050*
C40	0.3460 (2)	0.80819 (17)	−0.01888 (13)	0.0411 (5)
H40	0.3252 (5)	0.8212 (3)	−0.0722 (13)	0.049*
C32	1.1362 (2)	1.10841 (15)	0.37123 (12)	0.0387 (4)
H32	1.1473 (3)	1.1748 (16)	0.36747 (15)	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01575 (17)	0.01667 (17)	0.02039 (18)	0.00240 (13)	0.00380 (13)	0.00764 (14)
P2	0.01637 (17)	0.01721 (17)	0.01916 (18)	0.00092 (13)	0.00155 (13)	0.00790 (14)
O9	0.0162 (5)	0.0184 (5)	0.0230 (5)	0.0006 (4)	−0.0003 (4)	0.0035 (4)
O2	0.0166 (5)	0.0184 (5)	0.0228 (5)	0.0021 (4)	0.0029 (4)	0.0040 (4)
O8	0.0172 (5)	0.0242 (5)	0.0291 (6)	0.0043 (4)	0.0033 (4)	0.0145 (5)
O4	0.0189 (5)	0.0210 (5)	0.0242 (5)	−0.0032 (4)	−0.0018 (4)	0.0086 (4)
O3	0.0146 (5)	0.0244 (5)	0.0361 (6)	0.0051 (4)	0.0053 (4)	0.0169 (5)
C23	0.0208 (7)	0.0149 (6)	0.0190 (7)	0.0026 (5)	0.0011 (5)	0.0058 (5)
O10	0.0203 (5)	0.0218 (5)	0.0253 (5)	−0.0033 (4)	−0.0036 (4)	0.0093 (5)
O7	0.0269 (6)	0.0245 (5)	0.0235 (5)	0.0020 (4)	0.0068 (4)	0.0106 (4)
N1	0.0200 (6)	0.0308 (7)	0.0273 (7)	0.0079 (5)	0.0010 (5)	0.0119 (6)
O5	0.0269 (6)	0.0434 (7)	0.0304 (6)	0.0131 (5)	0.0052 (5)	0.0219 (5)
C22	0.0190 (7)	0.0165 (6)	0.0196 (7)	0.0009 (5)	−0.0006 (5)	0.0071 (5)
N2	0.0247 (7)	0.0295 (7)	0.0239 (6)	0.0123 (6)	0.0016 (5)	0.0100 (6)
C24	0.0221 (7)	0.0208 (7)	0.0197 (7)	0.0064 (6)	0.0013 (5)	0.0067 (6)
C7	0.0212 (7)	0.0230 (7)	0.0212 (7)	0.0023 (6)	0.0008 (6)	0.0080 (6)
C1	0.0172 (6)	0.0167 (6)	0.0194 (7)	0.0019 (5)	0.0017 (5)	0.0075 (5)
C16	0.0235 (7)	0.0184 (7)	0.0208 (7)	0.0014 (6)	0.0047 (6)	0.0010 (6)
C2	0.0187 (7)	0.0161 (6)	0.0192 (7)	0.0039 (5)	0.0033 (5)	0.0066 (5)
C37	0.0167 (7)	0.0290 (8)	0.0304 (8)	0.0088 (6)	0.0044 (6)	0.0122 (7)
O1	0.0262 (6)	0.0236 (5)	0.0251 (5)	0.0040 (4)	0.0088 (4)	0.0110 (4)
C4	0.0183 (7)	0.0324 (8)	0.0281 (8)	0.0044 (6)	0.0058 (6)	0.0109 (7)
C10	0.0227 (8)	0.0283 (8)	0.0328 (9)	0.0087 (7)	0.0030 (6)	0.0031 (7)
C3	0.0190 (7)	0.0219 (7)	0.0195 (7)	0.0047 (6)	0.0011 (5)	0.0072 (6)
C9	0.0137 (6)	0.0247 (7)	0.0340 (8)	0.0043 (6)	0.0010 (6)	0.0106 (7)
O11	0.0323 (6)	0.0561 (8)	0.0299 (6)	0.0225 (6)	0.0096 (5)	0.0252 (6)
O12	0.0249 (6)	0.0562 (9)	0.0417 (7)	0.0060 (6)	−0.0060 (5)	0.0215 (7)
C17	0.0320 (9)	0.0220 (7)	0.0316 (8)	0.0091 (6)	0.0073 (7)	0.0109 (7)
C25	0.0222 (8)	0.0307 (8)	0.0276 (8)	0.0075 (6)	0.0055 (6)	0.0093 (7)
C28	0.0230 (7)	0.0239 (7)	0.0216 (7)	0.0028 (6)	0.0000 (6)	0.0097 (6)
C36	0.0200 (7)	0.0417 (10)	0.0339 (9)	0.0135 (7)	0.0076 (6)	0.0188 (8)
C14	0.0252 (8)	0.0303 (8)	0.0250 (8)	0.0107 (7)	0.0007 (6)	0.0056 (7)
C31	0.0330 (9)	0.0247 (8)	0.0271 (8)	0.0053 (7)	−0.0001 (7)	0.0059 (7)
C8	0.0143 (7)	0.0323 (9)	0.0500 (11)	0.0047 (6)	0.0049 (7)	0.0223 (8)
C21	0.0345 (9)	0.0292 (8)	0.0265 (8)	0.0112 (7)	−0.0011 (7)	0.0060 (7)
C30	0.0206 (7)	0.0213 (7)	0.0180 (7)	0.0000 (6)	0.0011 (5)	0.0025 (6)
C26	0.0301 (8)	0.0344 (9)	0.0251 (8)	0.0056 (7)	0.0079 (7)	0.0125 (7)
C35	0.0295 (8)	0.0281 (8)	0.0282 (8)	0.0079 (7)	0.0047 (7)	0.0091 (7)
C29	0.0236 (8)	0.0265 (8)	0.0243 (8)	−0.0039 (6)	0.0043 (6)	−0.0011 (6)
C19	0.0346 (9)	0.0247 (8)	0.0277 (8)	−0.0018 (7)	0.0076 (7)	0.0055 (7)
C42	0.0247 (8)	0.0255 (8)	0.0354 (9)	0.0107 (6)	0.0045 (7)	0.0085 (7)
O6	0.0215 (6)	0.0889 (12)	0.0506 (9)	−0.0042 (7)	−0.0089 (6)	0.0404 (9)
C6	0.0279 (8)	0.0330 (8)	0.0205 (7)	0.0042 (7)	0.0028 (6)	0.0127 (7)
C18	0.0260 (8)	0.0335 (9)	0.0319 (9)	0.0082 (7)	0.0036 (7)	0.0077 (7)
C11	0.0357 (10)	0.0486 (11)	0.0265 (9)	0.0158 (9)	0.0033 (7)	0.0113 (8)
C27	0.0320 (9)	0.0307 (8)	0.0216 (7)	0.0042 (7)	0.0017 (6)	0.0125 (7)
C20	0.0543 (12)	0.0212 (8)	0.0293 (9)	0.0062 (8)	0.0048 (8)	0.0119 (7)
C5	0.0277 (8)	0.0350 (9)	0.0264 (8)	0.0038 (7)	0.0095 (7)	0.0135 (7)
C38	0.0359 (9)	0.0319 (9)	0.0304 (9)	0.0171 (8)	0.0012 (7)	0.0062 (7)
C15	0.0307 (9)	0.0243 (8)	0.0328 (9)	−0.0021 (7)	0.0109 (7)	−0.0038 (7)
C41	0.0367 (10)	0.0427 (10)	0.0282 (9)	0.0221 (8)	0.0050 (7)	0.0061 (8)
C34	0.0230 (8)	0.0537 (12)	0.0311 (9)	0.0096 (8)	0.0042 (7)	0.0101 (8)
C13	0.0360 (9)	0.0317 (9)	0.0345 (9)	0.0186 (8)	0.0004 (7)	0.0076 (7)
C33	0.0300 (9)	0.0445 (11)	0.0302 (9)	−0.0106 (8)	0.0033 (7)	0.0095 (8)
C12	0.0356 (10)	0.0463 (11)	0.0381 (10)	0.0201 (9)	0.0009 (8)	0.0214 (9)
C39	0.0545 (12)	0.0402 (10)	0.0408 (10)	0.0311 (10)	0.0054 (9)	0.0155 (9)
C40	0.0489 (12)	0.0548 (12)	0.0339 (10)	0.0331 (10)	0.0084 (8)	0.0198 (9)
C32	0.0515 (12)	0.0240 (8)	0.0293 (9)	−0.0042 (8)	0.0022 (8)	0.0094 (7)

Geometric parameters (Å, º)

P1—O1	1.4749 (11)	C28—C27	1.391 (2)
P1—O2	1.5670 (10)	C28—H28	0.940 (18)
P1—O3	1.5743 (11)	C36—H36A	1.005 (13)
P1—C1	1.8269 (14)	C36—H36B	1.005 (13)
P2—O7	1.4739 (11)	C14—C13	1.383 (2)
P2—O9	1.5634 (10)	C14—H14	0.958 (19)
P2—O8	1.5785 (11)	C31—C32	1.387 (2)
P2—C22	1.8255 (15)	C31—C30	1.388 (2)
O9—C29	1.4590 (18)	C31—H31	0.98 (2)
O2—C15	1.4653 (18)	C8—H8A	1.002 (13)
O8—C36	1.4654 (18)	C8—H8B	1.002 (13)
O4—C1	1.4228 (17)	C21—C20	1.388 (2)
O4—H400	0.83 (2)	C21—H21	0.93 (2)
O3—C8	1.4665 (18)	C30—C35	1.389 (2)
C23—C28	1.394 (2)	C30—C29	1.498 (2)
C23—C24	1.405 (2)	C26—C27	1.382 (2)
C23—C22	1.5238 (19)	C26—H26	0.992 (19)
O10—C22	1.4257 (17)	C35—C34	1.386 (2)
O10—H100	0.91 (2)	C35—H35	0.97 (2)
N1—O6	1.2182 (17)	C29—H29A	0.963 (13)
N1—O5	1.2202 (17)	C29—H29B	0.963 (13)
N1—C3	1.4740 (19)	C19—C20	1.372 (3)
C22—H22	0.987 (17)	C19—C18	1.381 (3)
N2—O12	1.2216 (17)	C19—H19	0.95 (2)
N2—O11	1.2229 (17)	C42—C41	1.374 (2)
N2—C24	1.4729 (19)	C42—H42	0.98 (2)
C24—C25	1.392 (2)	C6—C5	1.382 (2)
C7—C6	1.389 (2)	C6—H6	0.913 (19)
C7—C2	1.396 (2)	C18—H18	0.99 (2)
C7—H7	0.955 (18)	C11—C12	1.386 (3)
C1—C2	1.5183 (19)	C11—H11	0.94 (2)
C1—H1	0.968 (17)	C27—H27	0.93 (2)
C16—C17	1.386 (2)	C20—H20	0.91 (2)
C16—C21	1.386 (2)	C5—H5	0.971 (19)
C16—C15	1.495 (2)	C38—C39	1.386 (3)
C2—C3	1.401 (2)	C38—H38	0.99 (2)
C37—C38	1.387 (2)	C15—H15A	0.945 (14)
C37—C42	1.390 (2)	C15—H15B	0.945 (14)
C37—C36	1.500 (2)	C41—C40	1.384 (3)
C4—C5	1.384 (2)	C41—H41	0.98 (2)
C4—C3	1.393 (2)	C34—C33	1.377 (3)
C4—H4	0.926 (19)	C34—H34	0.99 (2)
C10—C11	1.381 (3)	C13—C12	1.380 (3)
C10—C9	1.387 (2)	C13—H13	0.94 (2)
C10—H10	0.94 (2)	C33—C32	1.378 (3)
C9—C14	1.389 (2)	C33—H33	0.93 (2)
C9—C8	1.498 (2)	C12—H12	0.94 (2)
C17—C18	1.384 (2)	C39—C40	1.380 (3)
C17—H17	0.98 (2)	C39—H39	0.97 (2)
C25—C26	1.383 (2)	C40—H40	0.96 (2)
C25—H25	0.948 (19)	C32—H32	0.92 (2)
O1—P1—O2	115.93 (6)	C32—C31—C30	120.22 (17)
O1—P1—O3	113.27 (6)	C32—C31—H31	119.9
O2—P1—O3	102.41 (6)	C30—C31—H31	119.9
O1—P1—C1	112.69 (6)	O3—C8—C9	106.44 (12)
O2—P1—C1	105.42 (6)	O3—C8—H8A	110.4
O3—P1—C1	106.07 (6)	C9—C8—H8A	110.4
O7—P2—O9	116.27 (6)	O3—C8—H8B	110.4
O7—P2—O8	112.73 (6)	C9—C8—H8B	110.4
O9—P2—O8	102.91 (6)	H8A—C8—H8B	108.6
O7—P2—C22	112.87 (6)	C16—C21—C20	120.52 (17)
O9—P2—C22	104.04 (6)	C16—C21—H21	119.7
O8—P2—C22	107.00 (6)	C20—C21—H21	119.7
C29—O9—P2	121.07 (9)	C31—C30—C35	119.51 (15)
C15—O2—P1	119.34 (9)	C31—C30—C29	120.41 (15)
C36—O8—P2	121.24 (9)	C35—C30—C29	120.07 (15)
C1—O4—H400	106.0 (14)	C27—C26—C25	119.23 (15)
C8—O3—P1	121.25 (9)	C27—C26—H26	120.4
C28—C23—C24	116.06 (13)	C25—C26—H26	120.4
C28—C23—C22	117.55 (13)	C34—C35—C30	119.92 (17)
C24—C23—C22	126.39 (13)	C34—C35—H35	120.0
C22—O10—H100	105.9 (14)	C30—C35—H35	120.0
O6—N1—O5	122.33 (14)	O9—C29—C30	107.49 (12)
O6—N1—C3	118.26 (13)	O9—C29—H29A	110.2
O5—N1—C3	119.42 (12)	C30—C29—H29A	110.2
O10—C22—C23	110.48 (11)	O9—C29—H29B	110.2
O10—C22—P2	103.59 (9)	C30—C29—H29B	110.2
C23—C22—P2	114.88 (10)	H29A—C29—H29B	108.5
O10—C22—H22	109.2	C20—C19—C18	119.87 (16)
C23—C22—H22	109.2	C20—C19—H19	120.1
P2—C22—H22	109.2	C18—C19—H19	120.1
O12—N2—O11	122.37 (14)	C41—C42—C37	120.89 (16)
O12—N2—C24	118.50 (13)	C41—C42—H42	119.6
O11—N2—C24	119.13 (13)	C37—C42—H42	119.6
C25—C24—C23	122.44 (14)	C5—C6—C7	120.42 (15)
C25—C24—N2	115.16 (13)	C5—C6—H6	119.8
C23—C24—N2	122.40 (13)	C7—C6—H6	119.8
C6—C7—C2	121.76 (14)	C19—C18—C17	120.38 (17)
C6—C7—H7	119.1	C19—C18—H18	119.8
C2—C7—H7	119.1	C17—C18—H18	119.8
O4—C1—C2	110.39 (11)	C10—C11—C12	120.18 (17)
O4—C1—P1	103.70 (9)	C10—C11—H11	119.9
C2—C1—P1	112.43 (9)	C12—C11—H11	119.9
O4—C1—H1	110.1	C26—C27—C28	120.53 (15)
C2—C1—H1	110.1	C26—C27—H27	119.7
P1—C1—H1	110.1	C28—C27—H27	119.7
C17—C16—C21	119.06 (15)	C19—C20—C21	120.02 (17)
C17—C16—C15	120.16 (16)	C19—C20—H20	120.0
C21—C16—C15	120.76 (16)	C21—C20—H20	120.0
C7—C2—C3	116.59 (13)	C6—C5—C4	119.38 (15)
C7—C2—C1	117.57 (13)	C6—C5—H5	120.3
C3—C2—C1	125.77 (13)	C4—C5—H5	120.3
C38—C37—C42	118.93 (16)	C39—C38—C37	120.22 (17)
C38—C37—C36	121.39 (15)	C39—C38—H38	119.9
C42—C37—C36	119.67 (15)	C37—C38—H38	119.9
C5—C4—C3	119.88 (15)	O2—C15—C16	109.09 (12)
C5—C4—H4	120.1	O2—C15—H15A	109.9
C3—C4—H4	120.1	C16—C15—H15A	109.9
C11—C10—C9	120.30 (16)	O2—C15—H15B	109.9
C11—C10—H10	119.9	C16—C15—H15B	109.9
C9—C10—H10	119.9	H15A—C15—H15B	108.3
C4—C3—C2	121.95 (14)	C42—C41—C40	119.88 (17)
C4—C3—N1	115.85 (13)	C42—C41—H41	120.1
C2—C3—N1	122.20 (13)	C40—C41—H41	120.1
C10—C9—C14	119.18 (16)	C33—C34—C35	120.16 (18)
C10—C9—C8	120.42 (15)	C33—C34—H34	119.9
C14—C9—C8	120.37 (15)	C35—C34—H34	119.9
C18—C17—C16	120.15 (16)	C12—C13—C14	119.93 (17)
C18—C17—H17	119.9	C12—C13—H13	120.0
C16—C17—H17	119.9	C14—C13—H13	120.0
C26—C25—C24	119.74 (15)	C34—C33—C32	120.37 (17)
C26—C25—H25	120.1	C34—C33—H33	119.8
C24—C25—H25	120.1	C32—C33—H33	119.8
C27—C28—C23	121.98 (15)	C13—C12—C11	119.87 (18)
C27—C28—H28	119.0	C13—C12—H12	120.1
C23—C28—H28	119.0	C11—C12—H12	120.1
O8—C36—C37	107.48 (12)	C40—C39—C38	120.17 (18)
O8—C36—H36A	110.2	C40—C39—H39	119.9
C37—C36—H36A	110.2	C38—C39—H39	119.9
O8—C36—H36B	110.2	C39—C40—C41	119.91 (18)
C37—C36—H36B	110.2	C39—C40—H40	120.0
H36A—C36—H36B	108.5	C41—C40—H40	120.0
C13—C14—C9	120.53 (16)	C33—C32—C31	119.81 (18)
C13—C14—H14	119.7	C33—C32—H32	120.1
C9—C14—H14	119.7	C31—C32—H32	120.1
O7—P2—O9—C29	−46.67 (14)	C11—C10—C9—C8	177.34 (15)
O8—P2—O9—C29	77.05 (13)	C21—C16—C17—C18	−0.2 (2)
C22—P2—O9—C29	−171.44 (12)	C15—C16—C17—C18	178.28 (15)
O1—P1—O2—C15	47.15 (14)	C23—C24—C25—C26	−0.6 (2)
O3—P1—O2—C15	−76.68 (13)	N2—C24—C25—C26	178.85 (15)
C1—P1—O2—C15	172.54 (12)	C24—C23—C28—C27	1.3 (2)
O7—P2—O8—C36	−29.37 (13)	C22—C23—C28—C27	−178.43 (14)
O9—P2—O8—C36	−155.41 (11)	P2—O8—C36—C37	−151.53 (11)
C22—P2—O8—C36	95.30 (12)	C38—C37—C36—O8	−101.89 (17)
O1—P1—O3—C8	30.14 (14)	C42—C37—C36—O8	76.69 (18)
O2—P1—O3—C8	155.73 (12)	C10—C9—C14—C13	0.5 (2)
C1—P1—O3—C8	−93.98 (12)	C8—C9—C14—C13	−177.33 (15)
C28—C23—C22—O10	17.28 (18)	P1—O3—C8—C9	−176.94 (10)
C24—C23—C22—O10	−162.46 (13)	C10—C9—C8—O3	−80.39 (18)
C28—C23—C22—P2	−99.44 (14)	C14—C9—C8—O3	97.46 (16)
C24—C23—C22—P2	80.82 (17)	C17—C16—C21—C20	0.5 (2)
O7—P2—C22—O10	73.45 (10)	C15—C16—C21—C20	−178.07 (15)
O9—P2—C22—O10	−159.63 (9)	C32—C31—C30—C35	0.6 (2)
O8—P2—C22—O10	−51.13 (10)	C32—C31—C30—C29	−178.51 (15)
O7—P2—C22—C23	−165.96 (10)	C24—C25—C26—C27	1.3 (3)
O9—P2—C22—C23	−39.04 (12)	C31—C30—C35—C34	−1.1 (2)
O8—P2—C22—C23	69.46 (11)	C29—C30—C35—C34	178.09 (15)
C28—C23—C24—C25	−0.7 (2)	P2—O9—C29—C30	−161.51 (11)
C22—C23—C24—C25	179.04 (14)	C31—C30—C29—O9	115.86 (16)
C28—C23—C24—N2	179.89 (13)	C35—C30—C29—O9	−63.28 (19)
C22—C23—C24—N2	−0.4 (2)	C38—C37—C42—C41	−0.3 (2)
O12—N2—C24—C25	14.3 (2)	C36—C37—C42—C41	−178.94 (15)
O11—N2—C24—C25	−165.73 (14)	C2—C7—C6—C5	0.4 (2)
O12—N2—C24—C23	−166.23 (14)	C20—C19—C18—C17	0.0 (3)
O11—N2—C24—C23	13.7 (2)	C16—C17—C18—C19	0.0 (2)
O1—P1—C1—O4	−74.02 (10)	C9—C10—C11—C12	0.3 (3)
O2—P1—C1—O4	158.60 (9)	C25—C26—C27—C28	−0.7 (3)
O3—P1—C1—O4	50.46 (10)	C23—C28—C27—C26	−0.7 (2)
O1—P1—C1—C2	166.73 (10)	C18—C19—C20—C21	0.2 (3)
O2—P1—C1—C2	39.35 (12)	C16—C21—C20—C19	−0.4 (3)
O3—P1—C1—C2	−68.79 (11)	C7—C6—C5—C4	0.6 (3)
C6—C7—C2—C3	−1.0 (2)	C3—C4—C5—C6	−0.9 (3)
C6—C7—C2—C1	−178.26 (14)	C42—C37—C38—C39	−0.1 (3)
O4—C1—C2—C7	−17.19 (18)	C36—C37—C38—C39	178.44 (16)
P1—C1—C2—C7	98.08 (14)	P1—O2—C15—C16	162.34 (11)
O4—C1—C2—C3	165.85 (13)	C17—C16—C15—O2	73.8 (2)
P1—C1—C2—C3	−78.88 (16)	C21—C16—C15—O2	−107.72 (17)
C5—C4—C3—C2	0.2 (2)	C37—C42—C41—C40	0.7 (3)
C5—C4—C3—N1	−179.72 (15)	C30—C35—C34—C33	0.6 (3)
C7—C2—C3—C4	0.7 (2)	C9—C14—C13—C12	−0.3 (3)
C1—C2—C3—C4	177.68 (14)	C35—C34—C33—C32	0.4 (3)
C7—C2—C3—N1	−179.35 (13)	C14—C13—C12—C11	0.0 (3)
C1—C2—C3—N1	−2.4 (2)	C10—C11—C12—C13	0.0 (3)
O6—N1—C3—C4	−9.3 (2)	C37—C38—C39—C40	0.3 (3)
O5—N1—C3—C4	170.73 (14)	C38—C39—C40—C41	0.1 (3)
O6—N1—C3—C2	170.71 (16)	C42—C41—C40—C39	−0.6 (3)
O5—N1—C3—C2	−9.2 (2)	C34—C33—C32—C31	−0.8 (3)
C11—C10—C9—C14	−0.5 (2)	C30—C31—C32—C33	0.3 (3)

Dimethyl [1-hydroxy-1-(4-nitrophenyl)ethyl]phosphonate (2b)

Crystal data

C10H14NO6P	Z = 2
Mr = 275.19	F(000) = 288
Triclinic, P1	Dx = 1.450 Mg m^−3
a = 8.1800 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4006 (6) Å	Cell parameters from 3426 reflections
c = 9.9661 (4) Å	θ = 4.6–31.3°
α = 102.173 (5)°	µ = 0.24 mm^−1
β = 94.897 (4)°	T = 173 K
γ = 107.504 (5)°	Block, colorless
V = 630.26 (6) Å^3	0.40 × 0.35 × 0.20 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	3827 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3070 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.028
ω scans	θmax = 30.5°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −11→11
Tmin = 0.948, Tmax = 1.000	k = −11→11
12564 measured reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.1729P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3827 reflections	Δρmax = 0.34 e Å^−3
176 parameters	Δρmin = −0.28 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.25993 (4)	0.15887 (5)	0.41073 (4)	0.02383 (11)
O4	−0.01562 (13)	0.24691 (13)	0.42662 (11)	0.0275 (2)
C3	0.12907 (16)	0.32849 (17)	0.24037 (13)	0.0214 (2)
O2	0.37141 (13)	0.12800 (15)	0.29430 (11)	0.0336 (3)
C5	0.07201 (16)	0.18886 (17)	0.31853 (13)	0.0207 (2)
O1	0.21030 (13)	0.02257 (14)	0.48551 (11)	0.0315 (2)
O3	0.37375 (14)	0.33881 (14)	0.50550 (11)	0.0367 (3)
C8	0.22597 (19)	0.57705 (19)	0.09385 (15)	0.0274 (3)
C9	0.10946 (19)	0.48879 (18)	0.28755 (15)	0.0279 (3)
H9	0.0657 (9)	0.5115 (5)	0.3667 (17)	0.033*
C10	−0.04346 (18)	0.01791 (18)	0.22095 (15)	0.0272 (3)
H10A	−0.0811 (12)	−0.0655 (10)	0.2735 (6)	0.041*
H10B	0.0208 (8)	−0.0219 (9)	0.1534 (10)	0.041*
H10C	−0.1422 (13)	0.0343 (4)	0.1749 (10)	0.041*
C11	0.20148 (18)	0.29652 (18)	0.11999 (14)	0.0258 (3)
H11	0.2176 (3)	0.185 (2)	0.0872 (6)	0.031*
N1	0.27623 (19)	0.70781 (18)	0.01358 (14)	0.0357 (3)
C13	0.25077 (19)	0.42079 (19)	0.04627 (15)	0.0282 (3)
H13	0.2968 (10)	0.4007 (5)	−0.0291 (16)	0.034*
O6	0.2299 (2)	0.83360 (17)	0.04140 (15)	0.0505 (3)
C15	0.1568 (2)	0.6144 (2)	0.21369 (16)	0.0312 (3)
H15	0.1421 (4)	0.723 (2)	0.2447 (7)	0.037*
O5	0.3616 (3)	0.6835 (2)	−0.07774 (19)	0.0765 (6)
C17	0.5299 (2)	0.0903 (3)	0.3215 (2)	0.0542 (6)
H17A	0.6078 (14)	0.1807 (16)	0.3884 (15)	0.081*
H17B	0.5770 (13)	0.075 (2)	0.2408 (12)	0.081*
H17C	0.5063 (5)	−0.0089 (18)	0.3526 (17)	0.081*
C18	0.3562 (3)	0.3990 (3)	0.64670 (19)	0.0507 (5)
H18A	0.2565 (18)	0.429 (2)	0.64949 (19)	0.076*
H18B	0.4518 (17)	0.4942 (18)	0.6898 (8)	0.076*
H18C	0.349 (2)	0.3126 (14)	0.6924 (8)	0.076*
H1A	−0.069 (3)	0.159 (3)	0.456 (3)	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01850 (16)	0.02768 (19)	0.02616 (18)	0.00507 (13)	0.00364 (12)	0.01212 (14)
O4	0.0301 (5)	0.0268 (5)	0.0299 (5)	0.0110 (4)	0.0150 (4)	0.0100 (4)
C3	0.0201 (6)	0.0243 (6)	0.0213 (6)	0.0088 (5)	0.0027 (4)	0.0072 (5)
O2	0.0254 (5)	0.0518 (7)	0.0353 (6)	0.0211 (5)	0.0108 (4)	0.0208 (5)
C5	0.0190 (5)	0.0221 (6)	0.0225 (6)	0.0075 (5)	0.0058 (4)	0.0065 (5)
O1	0.0246 (5)	0.0351 (6)	0.0406 (6)	0.0087 (4)	0.0068 (4)	0.0225 (5)
O3	0.0315 (6)	0.0364 (6)	0.0300 (5)	−0.0065 (5)	−0.0012 (4)	0.0105 (5)
C8	0.0290 (7)	0.0301 (7)	0.0275 (7)	0.0110 (6)	0.0065 (5)	0.0137 (6)
C9	0.0340 (7)	0.0280 (7)	0.0276 (7)	0.0147 (6)	0.0130 (6)	0.0097 (5)
C10	0.0236 (6)	0.0252 (7)	0.0293 (7)	0.0048 (5)	0.0022 (5)	0.0051 (5)
C11	0.0311 (7)	0.0252 (6)	0.0231 (6)	0.0119 (5)	0.0063 (5)	0.0058 (5)
N1	0.0443 (8)	0.0364 (7)	0.0346 (7)	0.0165 (6)	0.0127 (6)	0.0189 (6)
C13	0.0345 (7)	0.0333 (7)	0.0216 (6)	0.0149 (6)	0.0096 (5)	0.0090 (5)
O6	0.0756 (10)	0.0413 (7)	0.0533 (8)	0.0321 (7)	0.0246 (7)	0.0267 (6)
C15	0.0400 (8)	0.0279 (7)	0.0333 (7)	0.0170 (6)	0.0134 (6)	0.0120 (6)
O5	0.1234 (15)	0.0685 (10)	0.0812 (11)	0.0551 (11)	0.0753 (11)	0.0527 (9)
C17	0.0344 (9)	0.0907 (16)	0.0652 (13)	0.0394 (10)	0.0210 (9)	0.0448 (12)
C18	0.0494 (11)	0.0493 (11)	0.0326 (9)	−0.0051 (8)	0.0025 (8)	−0.0009 (8)

Geometric parameters (Å, º)

P1—O1	1.4708 (10)	C9—H9	0.902 (18)
P1—O2	1.5625 (11)	C10—H10A	0.955 (10)
P1—O3	1.5636 (11)	C10—H10B	0.955 (10)
P1—C5	1.8330 (13)	C10—H10C	0.955 (10)
O4—C5	1.4258 (15)	C11—C13	1.3831 (19)
O4—H1A	0.86 (3)	C11—H11	0.979 (17)
C3—C9	1.3914 (19)	N1—O6	1.2135 (18)
C3—C11	1.3940 (18)	N1—O5	1.2137 (19)
C3—C5	1.5228 (18)	C13—H13	0.876 (19)
O2—C17	1.4414 (18)	C15—H15	0.944 (19)
C5—C10	1.5292 (19)	C17—H17A	0.922 (13)
O3—C18	1.426 (2)	C17—H17B	0.922 (13)
C8—C13	1.380 (2)	C17—H17C	0.922 (13)
C8—C15	1.382 (2)	C18—H18A	0.926 (13)
C8—N1	1.4732 (18)	C18—H18B	0.926 (13)
C9—C15	1.3916 (19)	C18—H18C	0.926 (13)
O1—P1—O2	115.61 (6)	C5—C10—H10C	109.5
O1—P1—O3	114.01 (6)	H10A—C10—H10C	109.5
O2—P1—O3	102.79 (6)	H10B—C10—H10C	109.5
O1—P1—C5	112.77 (6)	C13—C11—C3	120.80 (13)
O2—P1—C5	103.31 (6)	C13—C11—H11	119.6
O3—P1—C5	107.26 (6)	C3—C11—H11	119.6
C5—O4—H1A	107.4 (16)	O6—N1—O5	123.31 (14)
C9—C3—C11	119.21 (12)	O6—N1—C8	118.61 (13)
C9—C3—C5	120.69 (12)	O5—N1—C8	118.08 (13)
C11—C3—C5	120.10 (12)	C8—C13—C11	118.65 (13)
C17—O2—P1	121.67 (11)	C8—C13—H13	120.7
O4—C5—C3	108.65 (10)	C11—C13—H13	120.7
O4—C5—C10	111.20 (10)	C8—C15—C9	118.46 (13)
C3—C5—C10	111.47 (11)	C8—C15—H15	120.8
O4—C5—P1	104.11 (8)	C9—C15—H15	120.8
C3—C5—P1	111.08 (8)	O2—C17—H17A	109.5
C10—C5—P1	110.10 (9)	O2—C17—H17B	109.5
C18—O3—P1	123.59 (11)	H17A—C17—H17B	109.5
C13—C8—C15	122.26 (13)	O2—C17—H17C	109.5
C13—C8—N1	118.35 (13)	H17A—C17—H17C	109.5
C15—C8—N1	119.39 (13)	H17B—C17—H17C	109.5
C3—C9—C15	120.60 (13)	O3—C18—H18A	109.5
C3—C9—H9	119.7	O3—C18—H18B	109.5
C15—C9—H9	119.7	H18A—C18—H18B	109.5
C5—C10—H10A	109.5	O3—C18—H18C	109.5
C5—C10—H10B	109.5	H18A—C18—H18C	109.5
H10A—C10—H10B	109.5	H18B—C18—H18C	109.5
O1—P1—O2—C17	−53.42 (16)	O1—P1—O3—C18	−33.54 (16)
O3—P1—O2—C17	71.43 (15)	O2—P1—O3—C18	−159.44 (14)
C5—P1—O2—C17	−177.09 (14)	C5—P1—O3—C18	92.04 (15)
C9—C3—C5—O4	6.74 (17)	C11—C3—C9—C15	1.8 (2)
C11—C3—C5—O4	−173.11 (11)	C5—C3—C9—C15	−178.05 (13)
C9—C3—C5—C10	129.61 (13)	C9—C3—C11—C13	−1.1 (2)
C11—C3—C5—C10	−50.23 (16)	C5—C3—C11—C13	178.70 (12)
C9—C3—C5—P1	−107.20 (13)	C13—C8—N1—O6	168.34 (15)
C11—C3—C5—P1	72.95 (14)	C15—C8—N1—O6	−12.0 (2)
O1—P1—C5—O4	64.33 (10)	C13—C8—N1—O5	−11.3 (2)
O2—P1—C5—O4	−170.16 (8)	C15—C8—N1—O5	168.37 (18)
O3—P1—C5—O4	−62.00 (10)	C15—C8—C13—C11	1.3 (2)
O1—P1—C5—C3	−178.91 (9)	N1—C8—C13—C11	−179.05 (13)
O2—P1—C5—C3	−53.40 (10)	C3—C11—C13—C8	−0.4 (2)
O3—P1—C5—C3	54.76 (10)	C13—C8—C15—C9	−0.6 (2)
O1—P1—C5—C10	−54.94 (11)	N1—C8—C15—C9	179.69 (13)
O2—P1—C5—C10	70.57 (10)	C3—C9—C15—C8	−0.9 (2)
O3—P1—C5—C10	178.73 (9)

Dimethyl (1-hydroxy-1-phenylethyl)phosphonate (2a)

Crystal data

C10H15O4P	F(000) = 488
Mr = 230.19	Dx = 1.341 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4780 (3) Å	Cell parameters from 8846 reflections
b = 17.2370 (6) Å	θ = 4.4–32.3°
c = 8.1357 (3) Å	µ = 0.23 mm^−1
β = 106.484 (4)°	T = 173 K
V = 1140.05 (7) Å^3	Block, colorless
Z = 4	0.40 × 0.35 × 0.25 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	3450 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3080 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.025
ω scans	θmax = 30.5°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −12→12
Tmin = 0.933, Tmax = 1.000	k = −24→24
22954 measured reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.2717P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3450 reflections	Δρmax = 0.35 e Å^−3
150 parameters	Δρmin = −0.19 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.81342 (3)	0.05200 (2)	0.72375 (3)	0.01989 (8)
O4	0.74312 (9)	0.04889 (5)	1.01317 (9)	0.02685 (16)
O3	0.66366 (9)	0.00078 (4)	0.62661 (10)	0.02942 (17)
O2	0.81828 (10)	0.11643 (4)	0.58901 (9)	0.02953 (17)
C1	0.75367 (11)	0.10611 (5)	0.89008 (11)	0.02041 (17)
C3	0.58302 (11)	0.14067 (5)	0.81672 (12)	0.02116 (17)
C2	0.88556 (13)	0.16627 (7)	0.97005 (14)	0.0311 (2)
H2A	0.8507 (6)	0.1966 (5)	1.0536 (12)	0.047*
H2B	0.9018 (9)	0.2002 (5)	0.8813 (9)	0.047*
H2C	0.9878 (10)	0.1401 (3)	1.0259 (12)	0.047*
C8	0.44531 (12)	0.10121 (6)	0.83454 (13)	0.0263 (2)
H8	0.4588 (2)	0.0529 (7)	0.8961 (9)	0.032*
C7	0.28845 (13)	0.13134 (7)	0.76373 (16)	0.0346 (2)
H7	0.1968 (16)	0.1046 (5)	0.7770 (3)	0.042*
C6	0.26717 (15)	0.20044 (7)	0.67392 (17)	0.0387 (3)
H6	0.1594 (19)	0.2211 (4)	0.6262 (8)	0.046*
C5	0.40312 (16)	0.23950 (7)	0.65363 (16)	0.0375 (3)
H5	0.3892 (3)	0.2861 (8)	0.5917 (11)	0.045*
C4	0.55997 (14)	0.20979 (6)	0.72474 (14)	0.0300 (2)
H4	0.6522 (15)	0.2369 (4)	0.7105 (3)	0.036*
C10	0.64171 (17)	−0.07743 (7)	0.67685 (18)	0.0402 (3)
H10A	0.7407 (11)	−0.1029 (3)	0.7034 (14)	0.060*
H10B	0.5680 (13)	−0.1025 (3)	0.5883 (11)	0.060*
H10C	0.6025 (14)	−0.07680 (7)	0.7709 (14)	0.060*
C9	0.8454 (2)	0.09599 (9)	0.42782 (16)	0.0458 (3)
H9A	0.9519 (13)	0.0810 (7)	0.4456 (3)	0.069*
H9B	0.8243 (14)	0.1378 (5)	0.3565 (10)	0.069*
H9C	0.7773 (13)	0.0563 (6)	0.3793 (9)	0.069*
O1	0.96698 (9)	0.00774 (5)	0.79093 (9)	0.02834 (16)
H1A	0.834 (2)	0.0365 (9)	1.059 (2)	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01892 (12)	0.02348 (13)	0.01659 (12)	0.00242 (8)	0.00395 (8)	−0.00086 (7)
O4	0.0205 (3)	0.0382 (4)	0.0223 (3)	0.0058 (3)	0.0068 (3)	0.0099 (3)
O3	0.0266 (3)	0.0256 (4)	0.0292 (4)	0.0006 (3)	−0.0032 (3)	−0.0042 (3)
O2	0.0403 (4)	0.0299 (4)	0.0225 (3)	0.0049 (3)	0.0154 (3)	0.0024 (3)
C1	0.0182 (4)	0.0251 (4)	0.0184 (4)	−0.0002 (3)	0.0060 (3)	−0.0005 (3)
C3	0.0218 (4)	0.0218 (4)	0.0202 (4)	0.0020 (3)	0.0064 (3)	−0.0010 (3)
C2	0.0264 (5)	0.0357 (5)	0.0301 (5)	−0.0071 (4)	0.0061 (4)	−0.0110 (4)
C8	0.0220 (4)	0.0273 (5)	0.0297 (5)	0.0022 (3)	0.0077 (4)	0.0032 (4)
C7	0.0207 (5)	0.0405 (6)	0.0416 (6)	0.0033 (4)	0.0070 (4)	0.0007 (5)
C6	0.0316 (5)	0.0393 (6)	0.0400 (6)	0.0145 (5)	0.0018 (5)	0.0007 (5)
C5	0.0462 (7)	0.0269 (5)	0.0361 (6)	0.0116 (5)	0.0065 (5)	0.0058 (4)
C4	0.0346 (5)	0.0237 (4)	0.0325 (5)	0.0007 (4)	0.0106 (4)	0.0031 (4)
C10	0.0422 (6)	0.0278 (5)	0.0454 (7)	−0.0065 (5)	0.0040 (5)	−0.0034 (5)
C9	0.0717 (9)	0.0474 (7)	0.0268 (5)	0.0092 (6)	0.0277 (6)	0.0031 (5)
O1	0.0212 (3)	0.0388 (4)	0.0240 (3)	0.0085 (3)	0.0048 (3)	−0.0004 (3)

Geometric parameters (Å, º)

P1—O1	1.4738 (7)	C8—C7	1.3911 (14)
P1—O3	1.5641 (8)	C8—H8	0.962 (14)
P1—O2	1.5692 (8)	C7—C6	1.3821 (18)
P1—C1	1.8294 (9)	C7—H7	0.936 (16)
O4—C1	1.4265 (11)	C6—C5	1.385 (2)
O4—H1A	0.787 (16)	C6—H6	0.955 (16)
O3—C10	1.4362 (14)	C5—C4	1.3887 (16)
O2—C9	1.4381 (13)	C5—H5	0.938 (17)
C1—C3	1.5212 (13)	C4—H4	0.946 (15)
C1—C2	1.5284 (13)	C10—H10A	0.917 (10)
C3—C4	1.3910 (14)	C10—H10B	0.917 (10)
C3—C8	1.3938 (13)	C10—H10C	0.917 (10)
C2—H2A	0.968 (9)	C9—H9A	0.910 (11)
C2—H2B	0.968 (9)	C9—H9B	0.910 (11)
C2—H2C	0.968 (9)	C9—H9C	0.910 (11)
O1—P1—O3	113.59 (5)	C3—C8—H8	119.8
O1—P1—O2	115.46 (4)	C6—C7—C8	120.44 (11)
O3—P1—O2	103.00 (4)	C6—C7—H7	119.8
O1—P1—C1	112.98 (4)	C8—C7—H7	119.8
O3—P1—C1	107.82 (4)	C7—C6—C5	119.60 (11)
O2—P1—C1	102.92 (4)	C7—C6—H6	120.2
C1—O4—H1A	105.5 (11)	C5—C6—H6	120.2
C10—O3—P1	122.56 (7)	C6—C5—C4	120.14 (11)
C9—O2—P1	120.42 (8)	C6—C5—H5	119.9
O4—C1—C3	107.70 (7)	C4—C5—H5	119.9
O4—C1—C2	110.75 (8)	C5—C4—C3	120.78 (10)
C3—C1—C2	113.63 (8)	C5—C4—H4	119.6
O4—C1—P1	104.62 (6)	C3—C4—H4	119.6
C3—C1—P1	109.97 (6)	O3—C10—H10A	109.5
C2—C1—P1	109.76 (7)	O3—C10—H10B	109.5
C4—C3—C8	118.68 (9)	H10A—C10—H10B	109.5
C4—C3—C1	121.28 (9)	O3—C10—H10C	109.5
C8—C3—C1	119.97 (8)	H10A—C10—H10C	109.5
C1—C2—H2A	109.5	H10B—C10—H10C	109.5
C1—C2—H2B	109.5	O2—C9—H9A	109.5
H2A—C2—H2B	109.5	O2—C9—H9B	109.5
C1—C2—H2C	109.5	H9A—C9—H9B	109.5
H2A—C2—H2C	109.5	O2—C9—H9C	109.5
H2B—C2—H2C	109.5	H9A—C9—H9C	109.5
C7—C8—C3	120.35 (10)	H9B—C9—H9C	109.5
C7—C8—H8	119.8
O1—P1—O3—C10	34.73 (11)	O4—C1—C3—C4	164.60 (9)
O2—P1—O3—C10	160.34 (9)	C2—C1—C3—C4	41.53 (12)
C1—P1—O3—C10	−91.28 (10)	P1—C1—C3—C4	−81.95 (10)
O1—P1—O2—C9	62.50 (11)	O4—C1—C3—C8	−18.28 (11)
O3—P1—O2—C9	−61.89 (10)	C2—C1—C3—C8	−141.34 (9)
C1—P1—O2—C9	−173.93 (10)	P1—C1—C3—C8	95.17 (9)
O1—P1—C1—O4	−56.46 (7)	C4—C3—C8—C7	−1.01 (15)
O3—P1—C1—O4	69.91 (6)	C1—C3—C8—C7	−178.21 (9)
O2—P1—C1—O4	178.34 (6)	C3—C8—C7—C6	0.44 (17)
O1—P1—C1—C3	−171.88 (6)	C8—C7—C6—C5	0.42 (19)
O3—P1—C1—C3	−45.51 (7)	C7—C6—C5—C4	−0.70 (19)
O2—P1—C1—C3	62.92 (7)	C6—C5—C4—C3	0.12 (18)
O1—P1—C1—C2	62.41 (8)	C8—C3—C4—C5	0.73 (15)
O3—P1—C1—C2	−171.22 (7)	C1—C3—C4—C5	177.90 (10)
O2—P1—C1—C2	−62.79 (8)

Dimethyl [(3,4-dimethoxyphenyl)(hydroxy)methyl]phosphonate (1b)

Crystal data

C11H17O6P	F(000) = 1168
Mr = 276.21	Dx = 1.388 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.464 (3) Å	Cell parameters from 2697 reflections
b = 8.5132 (4) Å	θ = 4.9–30.5°
c = 8.0044 (3) Å	µ = 0.23 mm^−1
β = 100.620 (5)°	T = 173 K
V = 2643.2 (2) Å^3	Block, colorless
Z = 8	0.30 × 0.20 × 0.05 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	4023 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2812 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.049
ω scans	θmax = 30.5°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −56→52
Tmin = 0.956, Tmax = 1.000	k = −9→12
13696 measured reflections	l = −8→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0536P)^2 + 1.0539P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
4023 reflections	Δρmax = 0.40 e Å^−3
178 parameters	Δρmin = −0.29 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.56049 (2)	0.22453 (5)	0.55325 (5)	0.02391 (13)
O5	0.69582 (3)	0.23316 (15)	0.89486 (15)	0.0296 (3)
O3	0.56238 (3)	0.39780 (15)	0.48490 (15)	0.0307 (3)
O2	0.52552 (3)	0.16331 (17)	0.44805 (17)	0.0345 (3)
C1	0.59193 (5)	0.1112 (2)	0.4634 (2)	0.0250 (3)
H1	0.58536 (13)	0.1140 (2)	0.334 (2)	0.030*
O6	0.72468 (3)	0.37616 (17)	0.67767 (17)	0.0361 (3)
C5	0.69270 (5)	0.3178 (2)	0.6143 (2)	0.0263 (4)
C2	0.62749 (4)	0.1814 (2)	0.5161 (2)	0.0240 (3)
O4	0.59076 (4)	−0.04869 (15)	0.51955 (17)	0.0326 (3)
C6	0.67557 (5)	0.3291 (2)	0.4488 (2)	0.0309 (4)
H6	0.6857 (2)	0.3837 (13)	0.3684 (18)	0.037*
C4	0.67689 (5)	0.23697 (19)	0.7345 (2)	0.0235 (3)
C7	0.64311 (5)	0.2601 (2)	0.3991 (2)	0.0280 (4)
H7	0.6329 (3)	0.2664 (3)	0.296 (3)	0.034*
C3	0.64461 (4)	0.1704 (2)	0.6854 (2)	0.0229 (3)
H3	0.6339 (2)	0.1161 (11)	0.7680 (17)	0.028*
C11	0.49302 (6)	0.2215 (3)	0.4808 (3)	0.0526 (6)
H11A	0.4912 (2)	0.200 (2)	0.592 (2)	0.079*
H11B	0.4751 (3)	0.1731 (18)	0.408 (2)	0.079*
H11C	0.4918 (2)	0.3290 (18)	0.463 (2)	0.079*
C10	0.58384 (6)	0.5159 (2)	0.5824 (3)	0.0385 (5)
H10A	0.5758 (3)	0.5353 (13)	0.6871 (17)	0.058*
H10B	0.5827 (3)	0.6118 (15)	0.5174 (11)	0.058*
H10C	0.6074 (3)	0.4793 (9)	0.6075 (16)	0.058*
C9	0.74214 (5)	0.4591 (3)	0.5627 (3)	0.0408 (5)
H9A	0.7451 (4)	0.3913 (11)	0.4715 (17)	0.061*
H9B	0.7642 (4)	0.4929 (17)	0.6217 (10)	0.061*
H9C	0.7288 (3)	0.5483 (16)	0.5184 (17)	0.061*
C8	0.68164 (6)	0.1518 (3)	1.0207 (2)	0.0416 (5)
H8A	0.6591 (4)	0.1996 (13)	1.0309 (14)	0.062*
H8B	0.6977 (3)	0.1593 (16)	1.1319 (16)	0.062*
H8C	0.6782 (4)	0.0395 (16)	0.9877 (11)	0.062*
O1	0.56403 (3)	0.21578 (15)	0.73921 (16)	0.0307 (3)
H1A	0.5808 (6)	−0.101 (3)	0.434 (3)	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0241 (2)	0.0244 (2)	0.0232 (2)	0.00164 (18)	0.00415 (16)	0.00097 (17)
O5	0.0308 (7)	0.0330 (7)	0.0233 (6)	−0.0076 (6)	0.0009 (5)	0.0031 (5)
O3	0.0371 (7)	0.0265 (6)	0.0277 (6)	0.0023 (6)	0.0042 (5)	0.0041 (5)
O2	0.0236 (6)	0.0410 (8)	0.0383 (7)	−0.0003 (6)	0.0043 (6)	−0.0048 (6)
C1	0.0261 (8)	0.0247 (8)	0.0236 (8)	0.0011 (7)	0.0034 (7)	−0.0020 (6)
O6	0.0300 (7)	0.0413 (8)	0.0373 (7)	−0.0113 (6)	0.0071 (6)	0.0067 (6)
C5	0.0259 (8)	0.0237 (8)	0.0302 (9)	−0.0010 (7)	0.0078 (7)	0.0013 (7)
C2	0.0236 (8)	0.0238 (8)	0.0249 (8)	0.0029 (7)	0.0054 (6)	−0.0031 (6)
O4	0.0377 (8)	0.0238 (6)	0.0343 (7)	−0.0005 (6)	0.0010 (6)	−0.0050 (5)
C6	0.0328 (10)	0.0323 (9)	0.0299 (9)	0.0021 (8)	0.0114 (8)	0.0065 (8)
C4	0.0269 (8)	0.0208 (7)	0.0233 (8)	0.0007 (7)	0.0057 (6)	−0.0004 (6)
C7	0.0282 (9)	0.0344 (10)	0.0216 (8)	0.0045 (8)	0.0049 (7)	0.0015 (7)
C3	0.0248 (8)	0.0214 (7)	0.0237 (8)	0.0006 (7)	0.0075 (7)	−0.0003 (6)
C11	0.0258 (10)	0.0718 (17)	0.0603 (15)	0.0026 (11)	0.0086 (10)	−0.0110 (12)
C10	0.0515 (12)	0.0224 (9)	0.0418 (11)	−0.0006 (9)	0.0089 (10)	−0.0023 (8)
C9	0.0329 (10)	0.0377 (11)	0.0538 (12)	−0.0058 (9)	0.0131 (9)	0.0176 (10)
C8	0.0386 (11)	0.0609 (14)	0.0251 (9)	−0.0103 (10)	0.0053 (8)	0.0068 (9)
O1	0.0356 (7)	0.0311 (7)	0.0267 (6)	0.0046 (6)	0.0088 (5)	0.0039 (5)

Geometric parameters (Å, º)

P1—O1	1.4711 (13)	C6—C7	1.399 (3)
P1—O2	1.5676 (14)	C6—H6	0.94 (2)
P1—O3	1.5797 (13)	C4—C3	1.383 (2)
P1—C1	1.8213 (18)	C7—H7	0.85 (2)
O5—C4	1.362 (2)	C3—H3	0.967 (19)
O5—C8	1.420 (2)	C11—H11A	0.926 (15)
O3—C10	1.447 (2)	C11—H11B	0.926 (15)
O2—C11	1.443 (2)	C11—H11C	0.926 (15)
C1—O4	1.437 (2)	C10—H10A	0.965 (13)
C1—C2	1.512 (2)	C10—H10B	0.965 (13)
C1—H1	1.018 (19)	C10—H10C	0.965 (13)
O6—C5	1.364 (2)	C9—H9A	0.954 (13)
O6—C9	1.433 (2)	C9—H9B	0.954 (14)
C5—C6	1.375 (3)	C9—H9C	0.954 (13)
C5—C4	1.417 (2)	C8—H8A	0.995 (13)
C2—C7	1.385 (2)	C8—H8B	0.995 (13)
C2—C3	1.401 (2)	C8—H8C	0.995 (13)
O4—H1A	0.85 (2)
O1—P1—O2	115.90 (8)	C2—C7—H7	119.7
O1—P1—O3	113.32 (7)	C6—C7—H7	119.7
O2—P1—O3	102.56 (8)	C4—C3—C2	120.14 (15)
O1—P1—C1	115.36 (8)	C4—C3—H3	119.9
O2—P1—C1	102.01 (8)	C2—C3—H3	119.9
O3—P1—C1	106.20 (8)	O2—C11—H11A	109.5
C4—O5—C8	117.46 (14)	O2—C11—H11B	109.5
C10—O3—P1	121.49 (12)	H11A—C11—H11B	109.5
C11—O2—P1	120.82 (14)	O2—C11—H11C	109.5
O4—C1—C2	111.66 (14)	H11A—C11—H11C	109.5
O4—C1—P1	108.34 (11)	H11B—C11—H11C	109.5
C2—C1—P1	110.16 (11)	O3—C10—H10A	109.5
O4—C1—H1	108.9	O3—C10—H10B	109.5
C2—C1—H1	108.9	H10A—C10—H10B	109.5
P1—C1—H1	108.9	O3—C10—H10C	109.5
C5—O6—C9	117.53 (15)	H10A—C10—H10C	109.5
O6—C5—C6	126.12 (16)	H10B—C10—H10C	109.5
O6—C5—C4	114.67 (16)	O6—C9—H9A	109.5
C6—C5—C4	119.21 (17)	O6—C9—H9B	109.5
C7—C2—C3	119.39 (16)	H9A—C9—H9B	109.5
C7—C2—C1	120.54 (16)	O6—C9—H9C	109.5
C3—C2—C1	120.05 (15)	H9A—C9—H9C	109.5
C1—O4—H1A	106.1 (15)	H9B—C9—H9C	109.5
C5—C6—C7	120.41 (17)	O5—C8—H8A	109.5
C5—C6—H6	119.8	O5—C8—H8B	109.5
C7—C6—H6	119.8	H8A—C8—H8B	109.5
O5—C4—C3	125.08 (15)	O5—C8—H8C	109.5
O5—C4—C5	114.69 (15)	H8A—C8—H8C	109.5
C3—C4—C5	120.23 (16)	H8B—C8—H8C	109.5
C2—C7—C6	120.61 (17)
O1—P1—O3—C10	33.33 (16)	P1—C1—C2—C3	70.10 (18)
O2—P1—O3—C10	159.02 (14)	O6—C5—C6—C7	178.26 (17)
C1—P1—O3—C10	−94.32 (15)	C4—C5—C6—C7	−0.8 (3)
O1—P1—O2—C11	52.68 (19)	C8—O5—C4—C3	1.3 (3)
O3—P1—O2—C11	−71.31 (18)	C8—O5—C4—C5	−179.03 (17)
C1—P1—O2—C11	178.83 (17)	O6—C5—C4—O5	1.2 (2)
O1—P1—C1—O4	54.60 (14)	C6—C5—C4—O5	−179.60 (16)
O2—P1—C1—O4	−71.91 (13)	O6—C5—C4—C3	−179.11 (15)
O3—P1—C1—O4	−178.97 (11)	C6—C5—C4—C3	0.0 (3)
O1—P1—C1—C2	−67.82 (14)	C3—C2—C7—C6	−0.5 (3)
O2—P1—C1—C2	165.67 (12)	C1—C2—C7—C6	178.12 (16)
O3—P1—C1—C2	58.62 (13)	C5—C6—C7—C2	1.0 (3)
C9—O6—C5—C6	0.8 (3)	O5—C4—C3—C2	−179.91 (16)
C9—O6—C5—C4	179.93 (16)	C5—C4—C3—C2	0.5 (3)
O4—C1—C2—C7	131.07 (17)	C7—C2—C3—C4	−0.3 (3)
P1—C1—C2—C7	−108.49 (16)	C1—C2—C3—C4	−178.88 (15)
O4—C1—C2—C3	−50.3 (2)

Dimethyl [(hydroxy)(phenyl)methyl]phosphonate (1a)

Crystal data

C9H13O4P	F(000) = 456
Mr = 216.16	Dx = 1.354 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4039 (5) Å	Cell parameters from 4166 reflections
b = 7.7007 (3) Å	θ = 4.6–30.9°
c = 16.6012 (7) Å	µ = 0.25 mm^−1
β = 99.149 (4)°	T = 173 K
V = 1060.69 (9) Å^3	Block, colorless
Z = 4	0.40 × 0.20 × 0.04 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer	3209 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2491 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm^-1	Rint = 0.041
ω scans	θmax = 30.5°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −12→12
Tmin = 0.846, Tmax = 1.000	k = −10→10
20344 measured reflections	l = −23→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.2064P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3209 reflections	Δρmax = 0.33 e Å^−3
139 parameters	Δρmin = −0.27 e Å^−3

Special details

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 > 2σ(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.

An Xcalibur, Sapphire3 detector equipped diffractometer was used with an Enhance Mo Kα X-ray radiation to collect all the intensity data. The program CrysAlis PRO (CrysAlisPro, Agilent, 2014) was used for data collection, space group determination and all data reduction purposes including empirical absorption correction using spherical harmonics. The initial structure models were provided by direct methods using SHELXT (Sheldrick, 2015a) and refined using full-matrix least-squares on F² using SHELXL (Sheldrick, 2015b). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P1	0.88836 (4)	0.22015 (5)	0.36890 (2)	0.02690 (11)
O4	0.69794 (12)	0.26302 (13)	0.23287 (6)	0.0324 (2)
O2	0.74859 (13)	0.27837 (13)	0.41599 (6)	0.0360 (2)
O1	0.90892 (11)	0.03033 (13)	0.36664 (5)	0.0307 (2)
O3	1.03594 (13)	0.32532 (14)	0.41315 (6)	0.0371 (2)
C1	0.85171 (16)	0.32552 (17)	0.26993 (8)	0.0278 (3)
H1	0.8441 (2)	0.451 (2)	0.27822 (17)	0.033*
C2	0.98395 (16)	0.29140 (17)	0.22002 (8)	0.0278 (3)
C3	0.97089 (19)	0.1600 (2)	0.16223 (8)	0.0349 (3)
H3	0.8787 (18)	0.0862 (14)	0.15465 (17)	0.042*
C8	0.6006 (2)	0.1790 (2)	0.40829 (11)	0.0458 (4)
H8A	0.5292	0.2134	0.3583	0.069*
H8B	0.5471	0.2013	0.4556	0.069*
H8C	0.6254	0.0549	0.4058	0.069*
C4	1.0920 (2)	0.1360 (3)	0.11544 (10)	0.0473 (4)
H4	1.0819 (3)	0.047 (2)	0.0756 (9)	0.057*
C7	1.12124 (19)	0.3953 (2)	0.23104 (10)	0.0408 (3)
H7	1.1322 (3)	0.4860 (19)	0.2714 (8)	0.049*
C9	1.1277 (2)	0.2684 (3)	0.48861 (11)	0.0541 (5)
H9A	1.0634 (10)	0.2545 (19)	0.5249 (6)	0.081*
H9B	1.2013 (16)	0.3464 (15)	0.5061 (6)	0.081*
H9C	1.1747 (16)	0.1692 (18)	0.4810 (2)	0.081*
C6	1.2420 (2)	0.3695 (3)	0.18461 (11)	0.0515 (5)
H6	1.333 (2)	0.4388 (17)	0.1927 (2)	0.062*
C5	1.2269 (2)	0.2405 (3)	0.12611 (11)	0.0523 (5)
H5	1.313 (2)	0.2229 (5)	0.0918 (8)	0.063*
H1A	0.653 (3)	0.334 (3)	0.1967 (13)	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.03003 (18)	0.02395 (17)	0.02590 (17)	−0.00095 (12)	0.00192 (12)	−0.00101 (12)
O4	0.0263 (5)	0.0321 (5)	0.0364 (5)	−0.0014 (4)	−0.0027 (4)	0.0061 (4)
O2	0.0401 (6)	0.0332 (5)	0.0364 (5)	−0.0027 (4)	0.0116 (4)	−0.0085 (4)
O1	0.0361 (5)	0.0253 (5)	0.0297 (5)	0.0015 (4)	0.0020 (4)	0.0011 (4)
O3	0.0405 (6)	0.0364 (5)	0.0310 (5)	−0.0091 (4)	−0.0049 (4)	0.0013 (4)
C1	0.0286 (6)	0.0221 (6)	0.0310 (6)	−0.0013 (5)	−0.0005 (5)	0.0013 (5)
C2	0.0288 (6)	0.0267 (6)	0.0261 (6)	−0.0014 (5)	−0.0010 (5)	0.0071 (5)
C3	0.0392 (8)	0.0368 (7)	0.0285 (6)	−0.0040 (6)	0.0046 (5)	0.0017 (5)
C8	0.0396 (8)	0.0516 (10)	0.0493 (9)	−0.0081 (7)	0.0172 (7)	−0.0115 (7)
C4	0.0526 (10)	0.0572 (11)	0.0341 (8)	0.0033 (8)	0.0129 (7)	0.0006 (7)
C7	0.0357 (8)	0.0413 (8)	0.0434 (8)	−0.0100 (6)	0.0001 (6)	0.0031 (7)
C9	0.0508 (10)	0.0636 (12)	0.0408 (9)	−0.0117 (9)	−0.0145 (8)	0.0096 (8)
C6	0.0335 (8)	0.0672 (12)	0.0531 (10)	−0.0107 (8)	0.0050 (7)	0.0173 (9)
C5	0.0421 (9)	0.0774 (13)	0.0404 (8)	0.0057 (9)	0.0159 (7)	0.0189 (9)

Geometric parameters (Å, º)

P1—O1	1.4731 (10)	C8—H8A	0.9800
P1—O3	1.5633 (10)	C8—H8B	0.9800
P1—O2	1.5760 (11)	C8—H8C	0.9800
P1—C1	1.8144 (14)	C4—C5	1.378 (3)
O4—C1	1.4238 (16)	C4—H4	0.95 (2)
O4—H1A	0.85 (2)	C7—C6	1.383 (2)
O2—C8	1.4485 (19)	C7—H7	0.962 (19)
O3—C9	1.4315 (19)	C9—H9A	0.878 (13)
C1—C2	1.5111 (19)	C9—H9B	0.878 (13)
C1—H1	0.977 (17)	C9—H9C	0.878 (13)
C2—C3	1.386 (2)	C6—C5	1.381 (3)
C2—C7	1.3918 (19)	C6—H6	0.92 (2)
C3—C4	1.388 (2)	C5—H5	1.00 (2)
C3—H3	0.953 (18)
O1—P1—O3	116.01 (6)	H8A—C8—H8B	109.5
O1—P1—O2	113.24 (6)	O2—C8—H8C	109.5
O3—P1—O2	102.58 (6)	H8A—C8—H8C	109.5
O1—P1—C1	115.11 (6)	H8B—C8—H8C	109.5
O3—P1—C1	101.63 (6)	C5—C4—C3	120.78 (17)
O2—P1—C1	106.82 (6)	C5—C4—H4	119.6
C1—O4—H1A	110.7 (15)	C3—C4—H4	119.6
C8—O2—P1	120.21 (10)	C6—C7—C2	120.72 (16)
C9—O3—P1	121.95 (10)	C6—C7—H7	119.6
O4—C1—C2	113.60 (11)	C2—C7—H7	119.6
O4—C1—P1	104.58 (9)	O3—C9—H9A	109.5
C2—C1—P1	112.65 (9)	O3—C9—H9B	109.5
O4—C1—H1	108.6	H9A—C9—H9B	109.5
C2—C1—H1	108.6	O3—C9—H9C	109.5
P1—C1—H1	108.6	H9A—C9—H9C	109.5
C3—C2—C7	118.89 (14)	H9B—C9—H9C	109.5
C3—C2—C1	121.47 (12)	C5—C6—C7	120.09 (17)
C7—C2—C1	119.63 (13)	C5—C6—H6	120.0
C2—C3—C4	120.01 (15)	C7—C6—H6	120.0
C2—C3—H3	120.0	C4—C5—C6	119.50 (17)
C4—C3—H3	120.0	C4—C5—H5	120.2
O2—C8—H8A	109.5	C6—C5—H5	120.2
O2—C8—H8B	109.5
O1—P1—O2—C8	−38.37 (13)	O4—C1—C2—C3	−22.67 (17)
O3—P1—O2—C8	−164.16 (12)	P1—C1—C2—C3	96.02 (13)
C1—P1—O2—C8	89.38 (13)	O4—C1—C2—C7	156.34 (12)
O1—P1—O3—C9	−42.43 (15)	P1—C1—C2—C7	−84.97 (14)
O2—P1—O3—C9	81.54 (14)	C7—C2—C3—C4	−1.3 (2)
C1—P1—O3—C9	−168.06 (14)	C1—C2—C3—C4	177.76 (13)
O1—P1—C1—O4	66.37 (10)	C2—C3—C4—C5	0.6 (2)
O3—P1—C1—O4	−167.41 (9)	C3—C2—C7—C6	0.7 (2)
O2—P1—C1—O4	−60.28 (10)	C1—C2—C7—C6	−178.31 (14)
O1—P1—C1—C2	−57.47 (11)	C2—C7—C6—C5	0.5 (3)
O3—P1—C1—C2	68.76 (10)	C3—C4—C5—C6	0.6 (3)
O2—P1—C1—C2	175.88 (9)	C7—C6—C5—C4	−1.1 (3)