Structure-directing weak phosphoryl XH...O=P (X = C, N) hydrogen bonds in cyclic oxazaphos­pholidines and oxazaphosphinanes

The structures of six cyclic oxazaphospholidines and three cyclic oxazaphosphinanes have been determined and their supramolecular structures have been compared. The molecules differ with respect to the functional groups attached to the central five- or six-membered rings, but have one phosphoryl group in common. The predominant feature in the supramolecular structures is the existence of relatively weak intermolecular phosphoryl XH...O=P (X = C, N) hydrogen bonds, creating in nearly all cases linear zigzag or double molecular chains. The molecular chains are in general linked to each other via very weak CH...π or usual hydrogen-bond interactions. A survey of the Cambridge Structural Database on similar XH...O=P interactions shows a very large flexibility of the XH...O angle, which is in agreement with the DFT calculation reported elsewhere. The strength of the XH...O=P interaction can therefore be considered as relatively weak to moderately strong, and is expected to play at least a role in the formation of secondary substructures.

S1. Comment

P-chiral organophosphorous compounds are used as ligands in catalysts for asymmetric organic synthesis and they are also functional as antibiotics, antitumorals and fungicides. We synthesized

S2. Refinement

In the absence of significant anomalous scattering, Friedel pairs were merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090–1098.

The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98, N—H in the range 0.86–0.89 N—H to 0.86 O—H = 0.82 Å) and U_iso(H) (in the range 1.2–1.5 times U_eq of the parent atom), after which the positions were refined with riding constraints.

Computing details

Data collection: SMART (Siemens, 1993) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); Enraf-Nonius (1989) for (V), (VI); CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Cell refinement: SAINT (Siemens ,1995) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); Enraf-Nonius (1989) for (V), (VI); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Data reduction: SAINT (Siemens ,1995) for (I), (II); P3/PC. (Siemens,1993) for (III), (IV); XCAD4 (Harms, K. \& Wocadlo, S., 1995) for (V), (VI); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) for (VII); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (VIII), (IX). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (I), (III), (IV), (V), (VI); SIR2002 (Burla et al., 2003) for (II), (VII), (IX); Superflip (Palatinus, 2006) for (VIII). For all compounds, program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures

Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.

(I) (2R,4S,5R)-3-tert-butyl-2-ethyl-4,5-diphenyl- [1,3,2]-oxazaphospholidine2-oxide

Crystal data

C20H26NO2P	F(000) = 1472
Mr = 343.39	Dx = 1.215 Mg m^−3
Orthorhombic, Pbca	Synchrotron radiation, λ = 0.50606 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9727 reflections
a = 10.5381 (8) Å	θ = 2.5–15.5°
b = 15.7519 (14) Å	µ = 0.07 mm^−1
c = 22.626 (2) Å	T = 120 K
V = 3755.8 (6) Å^3	Needle, translucent pale white
Z = 8	0.50 × 0.05 × 0.05 mm

Data collection

Bruker SMART diffractometer	4671 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.072
ω scans	θmax = 20.8°, θmin = 1.2°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −15→14
Tmin = 0.89, Tmax = 1.00	k = −19→22
22025 measured reflections	l = −31→33
6228 independent reflections

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.490 0.521 0.215
wR(F^2) = 0.052	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.36 e Å^−3
4671 reflections	Δρmin = −0.67 e Å^−3
218 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 8606.704
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.20146 (6)	0.26635 (4)	0.34674 (3)	0.0191
P2	0.27888 (2)	0.184807 (17)	0.324450 (11)	0.0160
N3	0.15860 (6)	0.11694 (5)	0.33016 (3)	0.0154
C4	0.03773 (5)	0.16098 (5)	0.34174 (3)	0.0141
C5	0.06840 (5)	0.25675 (5)	0.33148 (4)	0.0159
O6	0.34005 (6)	0.19264 (5)	0.26596 (3)	0.0230
C7	0.15291 (7)	0.03521 (5)	0.29651 (4)	0.0185
C8	0.04833 (4)	−0.02094 (4)	0.32232 (3)	0.0243
C9	0.12636 (4)	0.05319 (4)	0.23100 (3)	0.0233
C10	0.27949 (4)	−0.01118 (4)	0.30347 (4)	0.0286
C11	0.39522 (5)	0.17025 (5)	0.38171 (4)	0.0242
C12	0.50525 (4)	0.23301 (4)	0.37534 (4)	0.0299
C13	−0.01815 (6)	0.14236 (5)	0.40205 (4)	0.0148
C14	0.05647 (6)	0.12382 (5)	0.45115 (4)	0.0208
C15	0.00059 (6)	0.11188 (5)	0.50639 (4)	0.0264
C16	−0.12979 (6)	0.11829 (5)	0.51322 (4)	0.0250
C17	−0.20476 (6)	0.13579 (5)	0.46432 (4)	0.0222
C18	−0.14936 (5)	0.14741 (5)	0.40907 (4)	0.0184
C19	−0.01076 (7)	0.31753 (5)	0.36688 (4)	0.0165
C20	0.03056 (6)	0.34779 (5)	0.42134 (4)	0.0235
C21	−0.04800 (6)	0.39979 (5)	0.45509 (4)	0.0292
C22	−0.16764 (6)	0.42159 (5)	0.43454 (5)	0.0299
C23	−0.20932 (6)	0.39115 (5)	0.38023 (4)	0.0284
C24	−0.13078 (6)	0.33921 (5)	0.34610 (4)	0.0225
H25	−0.0235	0.1448	0.3124	0.0500*
H26	0.0570	0.2680	0.2901	0.0500*
H27	0.4271	0.1131	0.3803	0.0500*
H28	0.3567	0.1802	0.4193	0.0500*
H29	0.4748	0.2894	0.3748	0.0500*
H30	0.5614	0.2264	0.4083	0.0500*
H31	0.5505	0.2238	0.3385	0.0500*
H32	0.3477	0.0215	0.2868	0.0500*
H33	0.2725	−0.0630	0.2821	0.0500*
H34	0.2947	−0.0235	0.3435	0.0500*
H35	0.1980	0.0807	0.2139	0.0500*
H36	0.1106	0.0023	0.2113	0.0500*
H37	0.0555	0.0885	0.2274	0.0500*
H38	0.0622	−0.0301	0.3627	0.0500*
H39	−0.0335	0.0033	0.3164	0.0500*
H40	0.0531	−0.0744	0.3031	0.0500*
H41	0.1439	0.1186	0.4467	0.0500*
H42	0.0511	0.0968	0.5394	0.0500*
H43	−0.1666	0.1105	0.5503	0.0500*
H44	−0.2908	0.1394	0.4686	0.0500*
H45	−0.1995	0.1613	0.3764	0.0500*
H46	−0.1565	0.3177	0.3113	0.0500*
H47	−0.2872	0.4046	0.3667	0.0500*
H48	−0.2180	0.4567	0.4573	0.0500*
H49	−0.0212	0.4193	0.4915	0.0500*
H50	0.1112	0.3340	0.4346	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.01197 (7)	0.02140 (9)	0.02380 (9)	0.00045 (9)	0.00212 (9)	−0.00062 (9)
P2	0.01047 (6)	0.02233 (7)	0.01516 (7)	0.00164 (6)	0.00186 (6)	0.00170 (6)
N3	0.01180 (7)	0.01935 (9)	0.01509 (9)	0.00216 (9)	0.00222 (9)	0.00071 (9)
C4	0.01089 (7)	0.01962 (9)	0.01166 (9)	0.00192 (9)	0.00088 (9)	0.00096 (9)
C5	0.01260 (7)	0.02025 (9)	0.01478 (9)	0.00231 (9)	0.00112 (9)	0.00272 (9)
O6	0.01727 (7)	0.03161 (9)	0.02005 (9)	0.00062 (9)	0.00755 (9)	0.00340 (9)
C7	0.01707 (7)	0.01956 (9)	0.01876 (9)	0.00228 (9)	0.00370 (9)	−0.00010 (9)
C8	0.02436 (7)	0.02216 (9)	0.02642 (9)	−0.00229 (9)	0.00471 (9)	0.00206 (9)
C9	0.02626 (7)	0.02744 (9)	0.01630 (9)	0.00026 (9)	0.00373 (9)	−0.00290 (9)
C10	0.02264 (7)	0.02454 (9)	0.03856 (10)	0.00774 (9)	0.00336 (9)	0.00052 (9)
C11	0.01570 (7)	0.03357 (9)	0.02339 (9)	0.00302 (9)	−0.00415 (9)	0.00190 (9)
C12	0.01659 (7)	0.03512 (10)	0.03811 (10)	−0.00085 (9)	−0.00507 (9)	−0.00560 (9)
C13	0.01286 (7)	0.01897 (9)	0.01266 (9)	0.00077 (9)	0.00081 (9)	0.00141 (9)
C14	0.01406 (7)	0.03414 (9)	0.01418 (9)	0.00420 (9)	0.00078 (9)	0.00454 (9)
C15	0.02026 (7)	0.04497 (10)	0.01404 (9)	0.00709 (9)	0.00130 (9)	0.00670 (9)
C16	0.02120 (7)	0.03760 (10)	0.01611 (9)	0.00363 (9)	0.00556 (9)	0.00576 (9)
C17	0.01380 (7)	0.03351 (9)	0.01920 (9)	0.00096 (9)	0.00466 (9)	0.00355 (9)
C18	0.01260 (7)	0.02742 (9)	0.01512 (9)	−0.00017 (9)	0.00049 (9)	0.00171 (9)
C19	0.01417 (7)	0.01757 (9)	0.01789 (9)	0.00135 (9)	0.00227 (9)	0.00206 (9)
C20	0.01888 (7)	0.02824 (9)	0.02333 (9)	−0.00113 (9)	0.00083 (9)	−0.00585 (9)
C21	0.02826 (7)	0.02801 (9)	0.03129 (9)	−0.00291 (9)	0.00766 (9)	−0.01001 (9)
C22	0.02754 (7)	0.02284 (9)	0.03938 (10)	0.00372 (9)	0.01536 (9)	−0.00148 (9)
C23	0.02037 (7)	0.02922 (9)	0.03549 (10)	0.00918 (9)	0.00734 (9)	0.00759 (9)
C24	0.01727 (7)	0.02677 (9)	0.02338 (9)	0.00599 (9)	0.00115 (9)	0.00522 (9)

Geometric parameters (Å, º)

O1—P2	1.6030 (7)	C11—H28	0.956
O1—C5	1.4520 (8)	C12—H29	0.944
P2—N3	1.6632 (7)	C12—H30	0.957
P2—O6	1.4772 (7)	C12—H31	0.972
P2—C11	1.7984 (8)	C13—C14	1.3920 (11)
N3—C4	1.4739 (9)	C13—C18	1.3940 (9)
N3—C7	1.4969 (12)	C14—C15	1.3944 (11)
C4—C5	1.5602 (10)	C14—H41	0.931
C4—C13	1.5147 (11)	C15—C16	1.3863 (9)
C4—H25	0.959	C15—H42	0.948
C5—C19	1.5012 (11)	C16—C17	1.3871 (11)
C5—H26	0.961	C16—H43	0.932
C7—C8	1.5290 (10)	C17—C18	1.3918 (11)
C7—C9	1.5347 (12)	C17—H44	0.914
C7—C10	1.5291 (9)	C18—H45	0.935
C8—H38	0.937	C19—C20	1.3912 (12)
C8—H39	0.953	C19—C24	1.3919 (10)
C8—H40	0.949	C20—C21	1.3926 (11)
C9—H35	0.953	C20—H50	0.927
C9—H36	0.932	C21—C22	1.3870 (10)
C9—H37	0.935	C21—H49	0.924
C10—H32	0.961	C22—C23	1.3901 (14)
C10—H33	0.951	C22—H48	0.923
C10—H34	0.939	C23—C24	1.3968 (11)
C11—C12	1.5306 (8)	C23—H47	0.902
C11—H27	0.962	C24—H46	0.898
P2—O1—C5	109.47 (5)	P2—C11—H27	109.5
O1—P2—N3	95.90 (4)	C12—C11—H27	109.7
O1—P2—O6	115.91 (4)	P2—C11—H28	109.3
N3—P2—O6	117.12 (4)	C12—C11—H28	107.5
O1—P2—C11	102.86 (4)	H27—C11—H28	109.3
N3—P2—C11	112.43 (4)	C11—C12—H29	110.6
O6—P2—C11	111.02 (4)	C11—C12—H30	108.9
P2—N3—C4	111.71 (5)	H29—C12—H30	108.9
P2—N3—C7	122.95 (5)	C11—C12—H31	110.9
C4—N3—C7	117.43 (6)	H29—C12—H31	107.2
N3—C4—C5	104.46 (5)	H30—C12—H31	110.4
N3—C4—C13	113.89 (6)	C4—C13—C14	122.68 (6)
C5—C4—C13	113.69 (6)	C4—C13—C18	118.50 (7)
N3—C4—H25	109.4	C14—C13—C18	118.77 (7)
C5—C4—H25	107.1	C13—C14—C15	120.34 (6)
C13—C4—H25	108.0	C13—C14—H41	119.4
C4—C5—O1	105.39 (5)	C15—C14—H41	120.2
C4—C5—C19	114.97 (6)	C14—C15—C16	120.57 (7)
O1—C5—C19	110.09 (6)	C14—C15—H42	120.2
C4—C5—H26	107.3	C16—C15—H42	119.2
O1—C5—H26	109.4	C15—C16—C17	119.34 (7)
C19—C5—H26	109.5	C15—C16—H43	120.2
N3—C7—C8	109.40 (6)	C17—C16—H43	120.4
N3—C7—C9	109.86 (7)	C16—C17—C18	120.24 (6)
C8—C7—C9	110.14 (6)	C16—C17—H44	119.5
N3—C7—C10	108.88 (6)	C18—C17—H44	120.2
C8—C7—C10	108.25 (6)	C13—C18—C17	120.72 (7)
C9—C7—C10	110.28 (6)	C13—C18—H45	118.9
C7—C8—H38	110.4	C17—C18—H45	120.3
C7—C8—H39	111.5	C5—C19—C20	121.14 (6)
H38—C8—H39	110.0	C5—C19—C24	118.77 (8)
C7—C8—H40	107.5	C20—C19—C24	119.97 (7)
H38—C8—H40	107.5	C19—C20—C21	120.07 (7)
H39—C8—H40	109.9	C19—C20—H50	119.6
C7—C9—H35	109.4	C21—C20—H50	120.3
C7—C9—H36	109.6	C20—C21—C22	120.14 (8)
H35—C9—H36	109.8	C20—C21—H49	120.2
C7—C9—H37	109.8	C22—C21—H49	119.6
H35—C9—H37	109.1	C21—C22—C23	119.88 (7)
H36—C9—H37	109.1	C21—C22—H48	119.0
C7—C10—H32	110.9	C23—C22—H48	121.2
C7—C10—H33	106.9	C22—C23—C24	120.23 (7)
H32—C10—H33	108.5	C22—C23—H47	120.5
C7—C10—H34	110.3	C24—C23—H47	119.3
H32—C10—H34	111.1	C23—C24—C19	119.70 (8)
H33—C10—H34	109.0	C23—C24—H46	121.8
P2—C11—C12	111.48 (5)	C19—C24—H46	118.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H25···O6^i	0.96	2.40	3.244 (2)	146

Symmetry code: (i) x−1/2, y, −z+1/2.

(II) (2S,4S,5R)and(2R,4R,5S)-3-tert-butyl-2-ethyl-4,5- diphenyl-[1,3,2]-oxazaphospholidine2-oxide

Crystal data

C20H26NO2P	Z = 4
Mr = 343.39	F(000) = 736
Triclinic, P1	Dx = 1.224 Mg m^−3
Hall symbol: -P 1	Synchrotron radiation, λ = 0.50606 Å
a = 6.7231 (5) Å	Cell parameters from 11434 reflections
b = 11.9766 (6) Å	θ = 2.5–16.5°
c = 23.6865 (16) Å	µ = 0.07 mm^−1
α = 97.644 (3)°	T = 120 K
β = 93.038 (2)°	Needle, translucent pale white
γ = 98.742 (2)°	0.40 × 0.05 × 0.05 mm
V = 1863.1 (2) Å^3

Data collection

Bruker SMART diffractometer	7201 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.073
ω scans	θmax = 20.9°, θmin = 1.2°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
Tmin = 0.91, Tmax = 1.00	k = −17→17
32894 measured reflections	l = −34→33
11718 independent reflections

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.507 0.574 0.220
wR(F^2) = 0.053	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.48 e Å^−3
7201 reflections	Δρmin = −0.58 e Å^−3
434 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 660 (90)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.77651 (15)	0.31881 (9)	0.42493 (5)	0.0209
P2	0.81472 (5)	0.18934 (3)	0.410737 (16)	0.0171
N3	0.59819 (16)	0.14115 (10)	0.37339 (5)	0.0160
C4	0.47693 (18)	0.23247 (11)	0.36808 (6)	0.0144
C5	0.56125 (19)	0.32181 (11)	0.42069 (6)	0.0167
O6	1.00407 (15)	0.17922 (11)	0.38347 (5)	0.0285
C7	0.5095 (2)	0.02075 (12)	0.35146 (7)	0.0197
C8	0.6752 (2)	−0.05377 (13)	0.34813 (7)	0.0266
C9	0.3515 (3)	−0.02224 (14)	0.39119 (9)	0.0346
C10	0.4092 (3)	0.01434 (14)	0.29150 (8)	0.0321
C11	0.8173 (2)	0.13664 (14)	0.47865 (7)	0.0249
C12	1.0154 (3)	0.17880 (18)	0.51469 (8)	0.0358
C13	0.4924 (2)	0.28161 (11)	0.31219 (6)	0.0161
C14	0.3241 (2)	0.31951 (13)	0.28902 (7)	0.0220
C15	0.3346 (3)	0.37081 (14)	0.23960 (7)	0.0290
C16	0.5133 (3)	0.38401 (15)	0.21295 (7)	0.0326
C17	0.6823 (3)	0.34621 (16)	0.23553 (7)	0.0315
C18	0.6713 (2)	0.29432 (14)	0.28493 (6)	0.0233
C19	0.5196 (2)	0.44037 (12)	0.41757 (6)	0.0194
C20	0.3338 (3)	0.46618 (14)	0.43280 (7)	0.0279
C21	0.2833 (3)	0.57296 (16)	0.42753 (9)	0.0380
C22	0.4205 (3)	0.65441 (15)	0.40754 (8)	0.0389
C23	0.6063 (3)	0.62959 (14)	0.39270 (8)	0.0346
C24	0.6570 (3)	0.52238 (13)	0.39744 (7)	0.0260
O25	0.75529 (14)	0.70375 (8)	0.06658 (4)	0.0184
P26	0.71085 (5)	0.83190 (3)	0.081143 (15)	0.0150
N27	0.93126 (16)	0.88544 (9)	0.11615 (5)	0.0147
C28	1.05303 (18)	0.79439 (11)	0.12373 (5)	0.0134
C29	0.97127 (18)	0.70373 (11)	0.07130 (6)	0.0150
O30	0.52514 (15)	0.84066 (10)	0.11036 (5)	0.0249
C31	0.9832 (2)	1.00090 (11)	0.15068 (6)	0.0174
C32	0.8722 (3)	1.08434 (13)	0.12286 (8)	0.0282
C33	1.2104 (2)	1.04049 (13)	0.15114 (7)	0.0243
C34	0.9180 (2)	0.99958 (14)	0.21169 (7)	0.0257
C35	0.6924 (2)	0.87958 (13)	0.01208 (6)	0.0218
C36	0.5017 (2)	0.81638 (14)	−0.02358 (7)	0.0278
C37	1.03775 (19)	0.74499 (11)	0.17934 (6)	0.0149
C38	0.8540 (2)	0.71596 (13)	0.20296 (6)	0.0219
C39	0.8468 (2)	0.66298 (15)	0.25174 (7)	0.0280
C40	1.0230 (3)	0.63861 (15)	0.27774 (7)	0.0307
C41	1.2053 (3)	0.66725 (15)	0.25460 (7)	0.0278
C42	1.2132 (2)	0.72004 (12)	0.20559 (6)	0.0194
C43	1.01773 (19)	0.58654 (11)	0.07508 (6)	0.0155
C44	0.8778 (2)	0.50090 (12)	0.09169 (6)	0.0200
C45	0.9311 (2)	0.39454 (12)	0.09658 (7)	0.0232
C46	1.1236 (2)	0.37327 (13)	0.08559 (7)	0.0248
C47	1.2625 (2)	0.45848 (13)	0.06876 (7)	0.0256
C48	1.2102 (2)	0.56452 (12)	0.06352 (7)	0.0212
H49	0.5067	0.2949	0.4547	0.0500*
H50	0.3427	0.2031	0.3734	0.0500*
H51	0.7123	0.1664	0.4985	0.0500*
H52	0.7881	0.0561	0.4723	0.0500*
H53	1.0061	0.1512	0.5494	0.0500*
H54	1.1204	0.1496	0.4948	0.0500*
H55	1.0397	0.2584	0.5195	0.0500*
H56	0.7747	−0.0282	0.3249	0.0500*
H57	0.7314	−0.0561	0.3854	0.0500*
H58	0.6129	−0.1289	0.3309	0.0500*
H59	0.4197	−0.0239	0.4270	0.0500*
H60	0.2881	−0.0976	0.3762	0.0500*
H61	0.2553	0.0259	0.3961	0.0500*
H62	0.3508	−0.0588	0.2784	0.0500*
H63	0.3056	0.0581	0.2930	0.0500*
H64	0.5016	0.0385	0.2661	0.0500*
H65	0.7841	0.2681	0.3001	0.0500*
H66	0.2091	0.3113	0.3069	0.0500*
H67	0.2261	0.3963	0.2251	0.0500*
H68	0.5223	0.4172	0.1808	0.0500*
H69	0.8037	0.3530	0.2173	0.0500*
H70	0.2423	0.4113	0.4465	0.0500*
H71	0.1634	0.5892	0.4376	0.0500*
H72	0.3899	0.7249	0.4046	0.0500*
H73	0.6953	0.6818	0.3778	0.0500*
H74	0.7775	0.5052	0.3870	0.0500*
H75	1.1868	0.8207	0.1181	0.0500*
H76	1.0266	0.7294	0.0382	0.0500*
H77	0.8092	0.8672	−0.0068	0.0500*
H78	0.6885	0.9579	0.0180	0.0500*
H79	0.3885	0.8352	−0.0054	0.0500*
H80	0.5021	0.8392	−0.0594	0.0500*
H81	0.4990	0.7369	−0.0273	0.0500*
H82	0.7346	1.0637	0.1208	0.0500*
H83	0.9141	1.0894	0.0857	0.0500*
H84	0.9062	1.1575	0.1442	0.0500*
H85	1.2826	0.9936	0.1693	0.0500*
H86	1.2411	1.1166	0.1704	0.0500*
H87	1.2526	1.0401	0.1136	0.0500*
H88	0.9412	1.0745	0.2313	0.0500*
H89	0.9919	0.9516	0.2306	0.0500*
H90	0.7801	0.9710	0.2117	0.0500*
H91	1.3328	0.7363	0.1895	0.0500*
H92	1.3209	0.6502	0.2719	0.0500*
H93	1.0153	0.6023	0.3099	0.0500*
H94	0.7259	0.6464	0.2676	0.0500*
H95	0.7379	0.7323	0.1862	0.0500*
H96	1.3032	0.6215	0.0529	0.0500*
H97	1.3853	0.4454	0.0605	0.0500*
H98	1.1606	0.3049	0.0900	0.0500*
H99	0.8351	0.3376	0.1090	0.0500*
H100	0.7517	0.5152	0.1007	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0148 (5)	0.0197 (5)	0.0279 (5)	0.0016 (4)	−0.0040 (4)	0.0055 (4)
P2	0.01208 (16)	0.02038 (18)	0.02088 (18)	0.00461 (13)	0.00099 (13)	0.00844 (15)
N3	0.0135 (5)	0.0147 (5)	0.0215 (6)	0.0052 (4)	0.0004 (4)	0.0056 (5)
C4	0.0110 (5)	0.0139 (6)	0.0193 (6)	0.0035 (4)	0.0019 (5)	0.0048 (5)
C5	0.0154 (6)	0.0178 (6)	0.0180 (6)	0.0044 (5)	0.0004 (5)	0.0049 (5)
O6	0.0135 (5)	0.0382 (7)	0.0373 (7)	0.0073 (4)	0.0053 (4)	0.0138 (6)
C7	0.0196 (6)	0.0143 (6)	0.0263 (7)	0.0047 (5)	0.0025 (5)	0.0042 (6)
C8	0.0310 (8)	0.0228 (7)	0.0295 (8)	0.0145 (6)	0.0022 (6)	0.0044 (7)
C9	0.0289 (8)	0.0210 (7)	0.0569 (12)	0.0029 (6)	0.0141 (8)	0.0138 (8)
C10	0.0366 (9)	0.0200 (7)	0.0369 (9)	0.0071 (6)	−0.0140 (7)	−0.0024 (7)
C11	0.0259 (7)	0.0284 (8)	0.0231 (7)	0.0075 (6)	−0.0016 (6)	0.0109 (7)
C12	0.0329 (9)	0.0445 (11)	0.0314 (9)	0.0122 (8)	−0.0108 (7)	0.0094 (8)
C13	0.0165 (6)	0.0138 (6)	0.0179 (6)	0.0022 (5)	−0.0015 (5)	0.0035 (5)
C14	0.0207 (7)	0.0218 (7)	0.0239 (7)	0.0060 (5)	−0.0039 (5)	0.0049 (6)
C15	0.0335 (9)	0.0272 (8)	0.0279 (8)	0.0089 (7)	−0.0075 (7)	0.0096 (7)
C16	0.0441 (10)	0.0303 (9)	0.0248 (8)	0.0019 (7)	−0.0024 (7)	0.0151 (7)
C17	0.0310 (8)	0.0400 (10)	0.0253 (8)	0.0014 (7)	0.0057 (6)	0.0152 (8)
C18	0.0197 (7)	0.0292 (8)	0.0229 (7)	0.0043 (6)	0.0029 (5)	0.0103 (6)
C19	0.0246 (7)	0.0165 (6)	0.0167 (6)	0.0049 (5)	−0.0027 (5)	0.0012 (5)
C20	0.0295 (8)	0.0251 (8)	0.0305 (8)	0.0112 (6)	0.0016 (6)	0.0019 (7)
C21	0.0464 (11)	0.0317 (9)	0.0388 (10)	0.0245 (8)	−0.0028 (8)	−0.0031 (8)
C22	0.0655 (14)	0.0214 (8)	0.0316 (9)	0.0197 (8)	−0.0090 (9)	0.0009 (7)
C23	0.0564 (12)	0.0176 (7)	0.0282 (8)	0.0026 (7)	−0.0063 (8)	0.0051 (7)
C24	0.0328 (8)	0.0182 (7)	0.0270 (8)	0.0030 (6)	−0.0021 (6)	0.0057 (6)
O25	0.0137 (4)	0.0160 (5)	0.0252 (5)	0.0019 (4)	−0.0023 (4)	0.0045 (4)
P26	0.00939 (15)	0.01635 (16)	0.02064 (18)	0.00295 (12)	0.00081 (12)	0.00666 (14)
N27	0.0117 (5)	0.0124 (5)	0.0208 (5)	0.0029 (4)	0.0006 (4)	0.0043 (4)
C28	0.0098 (5)	0.0136 (5)	0.0180 (6)	0.0036 (4)	0.0015 (4)	0.0047 (5)
C29	0.0109 (5)	0.0160 (6)	0.0187 (6)	0.0025 (4)	0.0013 (5)	0.0037 (5)
O30	0.0119 (5)	0.0308 (6)	0.0343 (6)	0.0054 (4)	0.0061 (4)	0.0090 (5)
C31	0.0173 (6)	0.0131 (6)	0.0226 (7)	0.0035 (5)	0.0014 (5)	0.0038 (5)
C32	0.0332 (9)	0.0174 (7)	0.0357 (9)	0.0100 (6)	−0.0041 (7)	0.0051 (7)
C33	0.0189 (7)	0.0199 (7)	0.0316 (8)	−0.0031 (5)	0.0017 (6)	0.0023 (6)
C34	0.0289 (8)	0.0255 (7)	0.0231 (7)	0.0072 (6)	0.0070 (6)	−0.0002 (6)
C35	0.0196 (7)	0.0230 (7)	0.0240 (7)	0.0025 (5)	−0.0018 (5)	0.0099 (6)
C36	0.0245 (7)	0.0290 (8)	0.0304 (8)	0.0045 (6)	−0.0091 (6)	0.0099 (7)
C37	0.0145 (6)	0.0133 (6)	0.0173 (6)	0.0030 (5)	0.0001 (5)	0.0033 (5)
C38	0.0174 (6)	0.0279 (7)	0.0223 (7)	0.0032 (5)	0.0038 (5)	0.0103 (6)
C39	0.0280 (8)	0.0330 (9)	0.0254 (8)	0.0013 (7)	0.0060 (6)	0.0150 (7)
C40	0.0377 (9)	0.0318 (9)	0.0257 (8)	0.0057 (7)	0.0014 (7)	0.0152 (7)
C41	0.0279 (8)	0.0308 (8)	0.0264 (8)	0.0081 (6)	−0.0053 (6)	0.0097 (7)
C42	0.0166 (6)	0.0195 (6)	0.0233 (7)	0.0057 (5)	−0.0021 (5)	0.0053 (6)
C43	0.0161 (6)	0.0133 (6)	0.0175 (6)	0.0038 (5)	0.0004 (5)	0.0029 (5)
C44	0.0182 (6)	0.0173 (6)	0.0253 (7)	0.0021 (5)	0.0004 (5)	0.0070 (6)
C45	0.0268 (7)	0.0174 (7)	0.0256 (7)	0.0019 (6)	−0.0013 (6)	0.0066 (6)
C46	0.0306 (8)	0.0166 (6)	0.0278 (8)	0.0089 (6)	−0.0040 (6)	0.0017 (6)
C47	0.0207 (7)	0.0198 (7)	0.0366 (9)	0.0087 (5)	0.0002 (6)	−0.0005 (7)
C48	0.0183 (6)	0.0166 (6)	0.0289 (7)	0.0045 (5)	0.0035 (5)	0.0017 (6)

Geometric parameters (Å, º)

P2—O1	1.605 (2)	C17—H69	0.9400
P2—O6	1.472 (2)	C18—H65	0.9400
P2—N3	1.645 (2)	C20—H70	0.9300
P2—C11	1.805 (3)	C21—H71	0.8900
P26—O30	1.470 (2)	C22—H72	0.9100
P26—N27	1.654 (2)	C23—H73	0.9200
P26—O25	1.605 (2)	C24—H74	0.9000
P26—C35	1.807 (3)	C28—C29	1.553 (3)
O1—C5	1.451 (3)	C28—C37	1.516 (3)
O25—C29	1.450 (3)	C29—C43	1.498 (3)
N3—C4	1.475 (3)	C31—C32	1.529 (4)
N3—C7	1.486 (3)	C31—C33	1.529 (4)
N27—C31	1.491 (3)	C31—C34	1.534 (4)
N27—C28	1.483 (3)	C35—C36	1.533 (4)
C4—C13	1.521 (3)	C37—C38	1.400 (4)
C4—C5	1.551 (3)	C37—C42	1.395 (4)
C5—C19	1.498 (3)	C38—C39	1.390 (4)
C7—C10	1.527 (4)	C39—C40	1.395 (5)
C7—C8	1.529 (4)	C40—C41	1.384 (5)
C7—C9	1.532 (5)	C41—C42	1.394 (4)
C11—C12	1.522 (4)	C43—C44	1.395 (4)
C13—C14	1.396 (4)	C43—C48	1.393 (4)
C13—C18	1.392 (4)	C44—C45	1.393 (3)
C14—C15	1.392 (4)	C45—C46	1.388 (4)
C15—C16	1.384 (5)	C46—C47	1.389 (4)
C16—C17	1.391 (5)	C47—C48	1.387 (3)
C17—C18	1.397 (4)	C28—H75	0.9300
C19—C20	1.387 (4)	C29—H76	0.9500
C19—C24	1.394 (4)	C32—H82	0.9200
C20—C21	1.392 (5)	C32—H83	0.9500
C21—C22	1.388 (6)	C32—H84	0.9400
C22—C23	1.380 (6)	C33—H85	0.9300
C23—C24	1.395 (4)	C33—H86	0.9500
C4—H50	0.9400	C33—H87	0.9500
C5—H49	0.9800	C34—H88	0.9400
C8—H57	0.9500	C34—H89	0.9500
C8—H56	0.9300	C34—H90	0.9400
C8—H58	0.9600	C35—H77	0.9500
C9—H59	0.9500	C35—H78	0.9300
C9—H60	0.9500	C36—H79	0.9400
C9—H61	0.9300	C36—H80	0.9300
C10—H62	0.9100	C36—H81	0.9400
C10—H63	0.9300	C38—H95	0.9200
C10—H64	0.9300	C39—H94	0.9200
C11—H51	0.9600	C40—H93	0.9300
C11—H52	0.9500	C41—H92	0.9200
C12—H53	0.9300	C42—H91	0.9100
C12—H54	0.9500	C44—H100	0.9200
C12—H55	0.9300	C45—H99	0.9500
C14—H66	0.9000	C46—H98	0.9100
C15—H67	0.9000	C47—H97	0.8900
C16—H68	0.9100	C48—H96	0.9200
O1—P2—O6	113.21 (13)	C21—C20—H70	120.00
O1—P2—N3	96.02 (11)	C19—C20—H70	120.00
O1—P2—C11	105.03 (14)	C22—C21—H71	120.00
O6—P2—N3	119.21 (12)	C20—C21—H71	120.00
O6—P2—C11	111.04 (13)	C21—C22—H72	120.00
N3—P2—C11	110.67 (12)	C23—C22—H72	119.00
N27—P26—C35	111.18 (12)	C22—C23—H73	121.00
O25—P26—N27	96.46 (11)	C24—C23—H73	119.00
O25—P26—C35	103.73 (11)	C19—C24—H74	120.00
O25—P26—O30	113.94 (12)	C23—C24—H74	121.00
O30—P26—C35	110.75 (13)	N27—C28—C29	101.51 (17)
O30—P26—N27	119.06 (12)	N27—C28—C37	116.56 (19)
P2—O1—C5	109.54 (16)	C29—C28—C37	112.0 (2)
P26—O25—C29	109.59 (15)	O25—C29—C28	104.99 (18)
P2—N3—C7	128.14 (18)	O25—C29—C43	111.17 (19)
P2—N3—C4	111.97 (16)	C28—C29—C43	114.9 (2)
C4—N3—C7	119.54 (19)	N27—C31—C32	109.0 (2)
C28—N27—C31	121.12 (19)	N27—C31—C33	108.7 (2)
P26—N27—C31	125.57 (17)	N27—C31—C34	111.2 (2)
P26—N27—C28	111.09 (15)	C32—C31—C33	108.9 (2)
C5—C4—C13	112.6 (2)	C32—C31—C34	108.0 (2)
N3—C4—C13	114.38 (19)	C33—C31—C34	110.8 (2)
N3—C4—C5	102.21 (18)	P26—C35—C36	110.86 (19)
O1—C5—C4	104.65 (19)	C28—C37—C38	122.7 (2)
O1—C5—C19	111.3 (2)	C28—C37—C42	118.2 (2)
C4—C5—C19	115.1 (2)	C38—C37—C42	118.9 (2)
N3—C7—C10	109.4 (2)	C37—C38—C39	120.3 (3)
C8—C7—C9	110.2 (2)	C38—C39—C40	120.4 (3)
C8—C7—C10	108.4 (2)	C39—C40—C41	119.5 (3)
C9—C7—C10	109.4 (3)	C40—C41—C42	120.3 (3)
N3—C7—C8	110.1 (2)	C37—C42—C41	120.5 (3)
N3—C7—C9	109.3 (2)	C29—C43—C44	122.2 (2)
P2—C11—C12	112.6 (2)	C29—C43—C48	118.3 (2)
C14—C13—C18	119.3 (2)	C44—C43—C48	119.5 (2)
C4—C13—C14	118.6 (2)	C43—C44—C45	119.9 (2)
C4—C13—C18	122.1 (2)	C44—C45—C46	120.4 (2)
C13—C14—C15	120.6 (3)	C45—C46—C47	119.6 (2)
C14—C15—C16	119.9 (3)	C46—C47—C48	120.3 (3)
C15—C16—C17	120.1 (3)	C43—C48—C47	120.3 (2)
C16—C17—C18	120.0 (3)	N27—C28—H75	109.00
C13—C18—C17	120.2 (3)	C29—C28—H75	106.00
C5—C19—C20	118.1 (2)	C37—C28—H75	111.00
C5—C19—C24	122.2 (2)	O25—C29—H76	109.00
C20—C19—C24	119.6 (3)	C28—C29—H76	108.00
C19—C20—C21	120.4 (3)	C43—C29—H76	109.00
C20—C21—C22	119.8 (4)	C31—C32—H82	113.00
C21—C22—C23	120.1 (3)	C31—C32—H83	110.00
C22—C23—C24	120.4 (3)	C31—C32—H84	109.00
C19—C24—C23	119.8 (3)	H82—C32—H83	109.00
C5—C4—H50	108.00	H82—C32—H84	108.00
N3—C4—H50	108.00	H83—C32—H84	107.00
C13—C4—H50	111.00	C31—C33—H85	111.00
C19—C5—H49	110.00	C31—C33—H86	108.00
C4—C5—H49	108.00	C31—C33—H87	111.00
O1—C5—H49	107.00	H85—C33—H86	110.00
C7—C8—H56	112.00	H85—C33—H87	108.00
C7—C8—H57	110.00	H86—C33—H87	108.00
C7—C8—H58	107.00	C31—C34—H88	109.00
H57—C8—H58	110.00	C31—C34—H89	109.00
H56—C8—H57	111.00	C31—C34—H90	111.00
H56—C8—H58	107.00	H88—C34—H89	111.00
C7—C9—H59	108.00	H88—C34—H90	108.00
H59—C9—H60	109.00	H89—C34—H90	108.00
C7—C9—H60	110.00	P26—C35—H77	109.00
C7—C9—H61	111.00	P26—C35—H78	108.00
H60—C9—H61	110.00	C36—C35—H77	111.00
H59—C9—H61	109.00	C36—C35—H78	110.00
C7—C10—H64	112.00	H77—C35—H78	109.00
C7—C10—H63	109.00	C35—C36—H79	109.00
H63—C10—H64	111.00	C35—C36—H80	108.00
H62—C10—H63	107.00	C35—C36—H81	111.00
H62—C10—H64	109.00	H79—C36—H80	110.00
C7—C10—H62	110.00	H79—C36—H81	110.00
P2—C11—H52	109.00	H80—C36—H81	109.00
C12—C11—H51	108.00	C37—C38—H95	120.00
C12—C11—H52	112.00	C39—C38—H95	120.00
H51—C11—H52	110.00	C38—C39—H94	120.00
P2—C11—H51	106.00	C40—C39—H94	120.00
C11—C12—H53	109.00	C39—C40—H93	119.00
C11—C12—H54	108.00	C41—C40—H93	121.00
H54—C12—H55	110.00	C40—C41—H92	119.00
H53—C12—H55	112.00	C42—C41—H92	121.00
C11—C12—H55	109.00	C37—C42—H91	119.00
H53—C12—H54	110.00	C41—C42—H91	120.00
C15—C14—H66	121.00	C43—C44—H100	120.00
C13—C14—H66	119.00	C45—C44—H100	120.00
C14—C15—H67	120.00	C44—C45—H99	119.00
C16—C15—H67	120.00	C46—C45—H99	121.00
C15—C16—H68	121.00	C45—C46—H98	121.00
C17—C16—H68	119.00	C47—C46—H98	120.00
C18—C17—H69	119.00	C46—C47—H97	121.00
C16—C17—H69	121.00	C48—C47—H97	119.00
C13—C18—H65	119.00	C43—C48—H96	119.00
C17—C18—H65	120.00	C47—C48—H96	120.00

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H50···O6^i	0.94	2.28	3.196 (3)	165
C28—H75···O30^ii	0.93	2.27	3.179 (3)	165

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

(III) (2S,4S,5R)-3-tert-butyl-2-[(1S)-1-?uoro-1-methyl- 2-oxo-propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2- oxide

Crystal data

C22H27FNO3P	F(000) = 856
Mr = 403.43	Dx = 1.231 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15 reflections
a = 6.411 (2) Å	θ = 4–10°
b = 16.206 (4) Å	µ = 0.16 mm^−1
c = 21.242 (5) Å	T = 293 K
β = 99.51 (2)°	Needle, translucent pale white
V = 2176.7 (10) Å^3	0.40 × 0.05 × 0.02 mm
Z = 4

Data collection

Siemens P3 diffractometer	Rint = 0.057
Graphite monochromator	θmax = 21.1°, θmin = 1.6°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan ?	k = 0→16
Tmin = 0.86, Tmax = 0.96	l = −21→21
2740 measured reflections	2 standard reflections every 60 min
2355 independent reflections	intensity decay: 4.0%
558 reflections with I > 2.0σ(I)

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.128	H-atom parameters constrained
wR(F^2) = 0.144	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.701 0.529 0.357
S = 1.10	(Δ/σ)max = 0.006
558 reflections	Δρmax = 0.47 e Å^−3
113 parameters	Δρmin = −0.56 e Å^−3
11 restraints

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

	x	y	z	Uiso*/Ueq
O1	0.185 (3)	0.0205 (12)	0.7567 (9)	0.058 (6)*
P2	0.0609 (14)	0.0838 (6)	0.7064 (4)	0.045 (3)*
N3	0.225 (4)	0.1564 (14)	0.7211 (10)	0.036 (7)*
C4	0.402 (5)	0.1421 (18)	0.7719 (12)	0.044 (9)*
C5	0.404 (5)	0.0479 (18)	0.7790 (13)	0.043 (9)*
O6	−0.167 (3)	0.1005 (12)	0.7122 (9)	0.057 (6)*
C7	0.079 (5)	0.030 (2)	0.6328 (14)	0.055 (10)*
F8	0.301 (3)	0.0326 (12)	0.6251 (9)	0.089 (7)*
C9	0.022 (5)	−0.062 (2)	0.6355 (15)	0.073 (11)*
C10	−0.059 (6)	0.065 (2)	0.5700 (17)	0.075 (12)*
O11	0.048 (4)	0.0947 (15)	0.5309 (11)	0.087 (8)*
C12	−0.279 (5)	0.055 (2)	0.5596 (16)	0.079 (12)*
C13	0.510 (4)	0.0086 (18)	0.8395 (13)	0.043 (9)*
C14	0.381 (4)	−0.0333 (17)	0.8758 (12)	0.053 (9)*
C15	0.475 (4)	−0.066 (2)	0.9343 (13)	0.072 (11)*
C16	0.690 (4)	−0.0602 (19)	0.9573 (14)	0.065 (11)*
C17	0.829 (5)	−0.022 (2)	0.9223 (16)	0.080 (12)*
C18	0.725 (4)	0.015 (2)	0.8632 (15)	0.068 (11)*
C19	0.388 (4)	0.183 (2)	0.8342 (14)	0.049 (10)*
C20	0.205 (5)	0.183 (2)	0.8616 (13)	0.064 (11)*
C21	0.186 (5)	0.2242 (19)	0.9183 (13)	0.074 (11)*
C22	0.373 (4)	0.259 (2)	0.9501 (16)	0.084 (13)*
C23	0.564 (5)	0.264 (2)	0.9274 (14)	0.079 (12)*
C24	0.563 (6)	0.223 (2)	0.8693 (14)	0.086 (13)*
C25	0.203 (8)	0.246 (3)	0.689 (2)	0.107 (15)*
C26	0.383 (10)	0.241 (4)	0.641 (3)	0.22 (3)*
C27	0.250 (10)	0.309 (4)	0.728 (3)	0.24 (3)*
C28	0.035 (7)	0.249 (2)	0.6367 (19)	0.121 (17)*
H29	0.4836	0.0276	0.7465	0.0399*
H30	0.5335	0.1602	0.7581	0.0549*
H31	0.1190	−0.0884	0.6686	0.0791*
H32	0.0315	−0.0876	0.5953	0.0791*
H33	−0.1196	−0.0676	0.6442	0.0791*
H34	−0.3347	0.0671	0.5979	0.0895*
H35	−0.3128	−0.0012	0.5473	0.0895*
H36	−0.3432	0.0912	0.5262	0.0895*
H37	0.2377	−0.0406	0.8612	0.0478*
H38	0.3880	−0.0925	0.9593	0.0779*
H39	0.7398	−0.0832	0.9971	0.0690*
H40	0.9757	−0.0211	0.9350	0.0943*
H41	0.8032	0.0480	0.8398	0.0691*
H42	0.0866	0.1552	0.8413	0.0703*
H43	0.0602	0.2289	0.9341	0.0776*
H44	0.3664	0.2808	0.9902	0.1019*
H45	0.6802	0.2918	0.9495	0.0877*
H46	0.6880	0.2221	0.8524	0.1146*
H47	0.5304	0.2554	0.6704	0.1789*
H48	0.3401	0.2857	0.6046	0.1789*
H49	0.3792	0.1801	0.6232	0.1789*
H50	0.4023	0.3143	0.7365	0.1829*
H51	0.1975	0.3004	0.7676	0.1829*
H52	0.1883	0.3581	0.7074	0.1829*
H53	0.0347	0.1993	0.6119	0.1185*
H54	−0.0980	0.2538	0.6515	0.1185*
H55	0.0547	0.2954	0.6106	0.1185*

Geometric parameters (Å, º)

O1—P2	1.60 (2)	C16—C17	1.400 (10)
O1—C5	1.47 (3)	C16—H39	0.930
P2—N3	1.58 (2)	C17—C18	1.45 (4)
P2—O6	1.51 (2)	C17—H40	0.932
P2—C7	1.81 (3)	C18—H41	0.930
N3—C4	1.45 (3)	C19—C20	1.395 (10)
N3—C25	1.60 (4)	C19—C24	1.396 (10)
C4—C5	1.53 (4)	C20—C21	1.398 (10)
C4—C19	1.50 (3)	C20—H42	0.929
C4—H30	0.982	C21—C22	1.390 (10)
C5—C13	1.49 (3)	C21—H43	0.929
C5—H29	0.980	C22—C23	1.395 (10)
C7—F8	1.46 (3)	C22—H44	0.930
C7—C9	1.53 (4)	C23—C24	1.400 (10)
C7—C10	1.58 (4)	C23—H45	0.928
C9—H31	0.960	C24—H46	0.930
C9—H32	0.962	C25—C26	1.66 (6)
C9—H33	0.962	C25—C27	1.31 (6)
C10—O11	1.26 (3)	C25—C28	1.42 (5)
C10—C12	1.41 (4)	C26—H47	1.065
C12—H34	0.961	C26—H48	1.064
C12—H35	0.960	C26—H49	1.065
C12—H36	0.960	C27—H50	0.965
C13—C14	1.395 (9)	C27—H51	0.965
C13—C18	1.393 (10)	C27—H52	0.964
C14—C15	1.393 (10)	C28—H53	0.959
C14—H37	0.929	C28—H54	0.960
C15—C16	1.389 (10)	C28—H55	0.960
C15—H38	0.932
P2—O1—C5	111.4 (17)	C15—C16—C17	122 (3)
O1—P2—N3	95.9 (13)	C15—C16—H39	117.7
O1—P2—O6	116.3 (12)	C17—C16—H39	120.4
N3—P2—O6	118.2 (13)	C16—C17—C18	114 (3)
O1—P2—C7	99.8 (14)	C16—C17—H40	123.5
N3—P2—C7	113.4 (13)	C18—C17—H40	122.9
O6—P2—C7	111.0 (14)	C17—C18—C13	125 (3)
P2—N3—C4	116 (2)	C17—C18—H41	119.3
P2—N3—C25	126 (2)	C13—C18—H41	116.0
C4—N3—C25	118 (3)	C4—C19—C20	123 (3)
N3—C4—C5	103 (2)	C4—C19—C24	121 (2)
N3—C4—C19	116 (2)	C20—C19—C24	116 (3)
C5—C4—C19	111 (2)	C19—C20—C21	124 (3)
N3—C4—H30	109.5	C19—C20—H42	119.1
C5—C4—H30	109.4	C21—C20—H42	116.9
C19—C4—H30	108.0	C20—C21—C22	115 (3)
C4—C5—O1	106 (2)	C20—C21—H43	123.8
C4—C5—C13	120 (3)	C22—C21—H43	121.3
O1—C5—C13	115 (2)	C21—C22—C23	126 (3)
C4—C5—H29	105.2	C21—C22—H44	115.9
O1—C5—H29	104.6	C23—C22—H44	118.0
C13—C5—H29	104.4	C22—C23—C24	114 (3)
P2—C7—F8	106 (2)	C22—C23—H45	122.1
P2—C7—C9	113 (2)	C24—C23—H45	124.3
F8—C7—C9	106 (3)	C23—C24—C19	125 (3)
P2—C7—C10	116 (2)	C23—C24—H46	117.8
F8—C7—C10	108 (2)	C19—C24—H46	116.9
C9—C7—C10	107 (3)	N3—C25—C26	101 (3)
C7—C9—H31	109.5	N3—C25—C27	116 (5)
C7—C9—H32	109.7	C26—C25—C27	108 (5)
H31—C9—H32	109.2	N3—C25—C28	111 (4)
C7—C9—H33	109.9	C26—C25—C28	92 (4)
H31—C9—H33	109.4	C27—C25—C28	123 (5)
H32—C9—H33	109.2	C25—C26—H47	106.2
C7—C10—O11	114 (3)	C25—C26—H48	107.4
C7—C10—C12	120 (3)	H47—C26—H48	112.0
O11—C10—C12	126 (3)	C25—C26—H49	107.1
C10—C12—H34	110.1	H47—C26—H49	111.9
C10—C12—H35	109.3	H48—C26—H49	112.0
H34—C12—H35	109.2	C25—C27—H50	107.9
C10—C12—H36	109.6	C25—C27—H51	110.9
H34—C12—H36	109.2	H50—C27—H51	110.0
H35—C12—H36	109.3	C25—C27—H52	108.5
C5—C13—C14	117 (2)	H50—C27—H52	109.7
C5—C13—C18	124 (3)	H51—C27—H52	109.7
C14—C13—C18	119 (3)	C25—C28—H53	110.1
C13—C14—C15	118 (3)	C25—C28—H54	110.1
C13—C14—H37	121.4	H53—C28—H54	109.3
C15—C14—H37	120.3	C25—C28—H55	108.9
C14—C15—C16	123 (3)	H53—C28—H55	109.2
C14—C15—H38	118.4	H54—C28—H55	109.2
C16—C15—H38	118.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H30···O6^i	0.98	2.49	3.30 (4)	139

Symmetry code: (i) x+1, y, z.

(IV) (2R,4R,5S)-3-tert-butyl-2-[(1S)-1-fluoro-1-methyl- 2-oxo-propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2- oxide.

Crystal data

C22H27FNO3P	F(000) = 856
Mr = 403.43	Dx = 1.248 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13 reflections
a = 19.252 (2) Å	θ = 4.2–12.3°
b = 6.584 (1) Å	µ = 0.16 mm^−1
c = 17.295 (2) Å	T = 293 K
β = 101.73 (2)°	Needle, translucent pale white
V = 2146.5 (5) Å^3	0.20 × 0.06 × 0.04 mm
Z = 4

Data collection

Siemens P3 diffractometer	Rint = 0.041
Graphite monochromator	θmax = 23.1°, θmin = 2.2°
ω/2θ scans	h = −21→20
Absorption correction: ψ scan ?	k = −7→0
Tmin = 0.85, Tmax = 0.94	l = 0→19
3395 measured reflections	3 standard reflections every 60 min
2972 independent reflections	intensity decay: 0.2%
660 reflections with I > 2.0σ(I)

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.113	H-atom parameters constrained
wR(F^2) = 0.126	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 0.676 0.602 0.331
S = 1.18	(Δ/σ)max = 0.000028
660 reflections	Δρmax = 0.71 e Å^−3
113 parameters	Δρmin = −0.63 e Å^−3
11 restraints

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

	x	y	z	Uiso*/Ueq
O1	0.2699 (7)	0.1501 (18)	0.7518 (8)	0.043 (4)*
P2	0.3135 (3)	0.0756 (11)	0.8359 (4)	0.051 (2)*
N3	0.2917 (8)	0.266 (2)	0.8846 (10)	0.039 (5)*
C4	0.2426 (9)	0.409 (3)	0.8394 (11)	0.036 (5)*
C5	0.2556 (11)	0.366 (3)	0.7548 (12)	0.041 (7)*
O6	0.3015 (8)	−0.139 (2)	0.8554 (9)	0.061 (5)*
C7	0.4082 (10)	0.084 (3)	0.8207 (11)	0.031 (5)*
F8	0.4234 (6)	0.298 (2)	0.8233 (7)	0.066 (4)*
C9	0.4624 (13)	−0.018 (4)	0.8840 (15)	0.084 (9)*
C10	0.4086 (12)	0.015 (4)	0.7363 (15)	0.057 (8)*
O11	0.4224 (10)	0.141 (3)	0.6923 (12)	0.092 (6)*
C12	0.3993 (13)	−0.203 (4)	0.7251 (15)	0.080 (9)*
C13	0.1992 (10)	0.426 (3)	0.6856 (11)	0.049 (6)*
C14	0.1503 (10)	0.288 (4)	0.6446 (11)	0.058 (7)*
C15	0.0974 (11)	0.343 (3)	0.5802 (11)	0.056 (7)*
C16	0.0990 (12)	0.541 (3)	0.5529 (14)	0.065 (7)*
C17	0.1483 (12)	0.682 (4)	0.5902 (14)	0.071 (8)*
C18	0.2004 (12)	0.623 (3)	0.6574 (14)	0.062 (7)*
C19	0.1676 (11)	0.385 (3)	0.8387 (14)	0.060 (8)*
C20	0.1271 (10)	0.559 (4)	0.8379 (13)	0.063 (7)*
C21	0.0545 (10)	0.563 (4)	0.8357 (15)	0.085 (8)*
C22	0.0235 (13)	0.376 (3)	0.8445 (15)	0.076 (8)*
C23	0.0597 (10)	0.192 (4)	0.8495 (14)	0.074 (8)*
C24	0.1317 (10)	0.206 (3)	0.8474 (13)	0.060 (7)*
C25	0.3178 (11)	0.302 (4)	0.9738 (13)	0.057 (7)*
C26	0.2598 (13)	0.402 (4)	1.0065 (16)	0.089 (9)*
C27	0.3345 (13)	0.098 (4)	1.0165 (15)	0.083 (9)*
C28	0.3811 (12)	0.445 (4)	0.9839 (15)	0.075 (8)*
H29	0.2990	0.4379	0.7495	0.0532*
H30	0.2577	0.5483	0.8550	0.0474*
H31	0.4631	0.0467	0.9338	0.0792*
H32	0.5085	−0.0069	0.8711	0.0792*
H33	0.4505	−0.1592	0.8874	0.0792*
H34	0.3513	−0.2391	0.7269	0.0995*
H35	0.4091	−0.2408	0.6749	0.0995*
H36	0.4312	−0.2735	0.7663	0.0995*
H37	0.1522	0.1538	0.6620	0.0610*
H38	0.0633	0.2500	0.5563	0.0687*
H39	0.0654	0.5807	0.5088	0.0811*
H40	0.1486	0.8129	0.5701	0.0955*
H41	0.2330	0.7163	0.6839	0.0939*
H42	0.1500	0.6835	0.8377	0.1030*
H43	0.0283	0.6827	0.8285	0.1202*
H44	−0.0239	0.3739	0.8486	0.0973*
H45	0.0375	0.0678	0.8523	0.0841*
H46	0.1575	0.0854	0.8507	0.0714*
H47	0.3682	0.5695	0.9556	0.0890*
H48	0.3971	0.4746	1.0390	0.0890*
H49	0.4184	0.3797	0.9640	0.0890*
H50	0.3486	0.1221	1.0723	0.1182*
H51	0.3722	0.0317	0.9979	0.1182*
H52	0.2931	0.0136	1.0065	0.1182*
H53	0.2733	0.4064	1.0631	0.0813*
H54	0.2522	0.5386	0.9864	0.0813*
H55	0.2169	0.3252	0.9913	0.0813*

Geometric parameters (Å, º)

O1—P2	1.602 (14)	C16—C17	1.390 (9)
O1—C5	1.45 (2)	C16—H39	0.932
P2—N3	1.613 (17)	C17—C18	1.43 (3)
P2—O6	1.483 (16)	C17—H40	0.931
P2—C7	1.896 (19)	C18—H41	0.931
N3—C4	1.45 (2)	C19—C20	1.388 (9)
N3—C25	1.54 (2)	C19—C24	1.389 (9)
C4—C5	1.56 (3)	C20—C21	1.390 (9)
C4—C19	1.45 (3)	C20—H42	0.929
C4—H30	0.981	C21—C22	1.390 (9)
C5—C13	1.50 (3)	C21—H43	0.928
C5—H29	0.980	C22—C23	1.394 (9)
C7—F8	1.44 (2)	C22—H44	0.930
C7—C9	1.51 (3)	C23—C24	1.397 (9)
C7—C10	1.53 (3)	C23—H45	0.929
C9—H31	0.959	C24—H46	0.930
C9—H32	0.961	C25—C26	1.50 (3)
C9—H33	0.961	C25—C27	1.53 (3)
C10—O11	1.19 (3)	C25—C28	1.52 (3)
C10—C12	1.46 (3)	C26—H53	0.962
C12—H34	0.960	C26—H54	0.961
C12—H35	0.958	C26—H55	0.960
C12—H36	0.958	C27—H50	0.960
C13—C14	1.391 (9)	C27—H51	0.959
C13—C18	1.387 (9)	C27—H52	0.960
C14—C15	1.394 (9)	C28—H47	0.961
C14—H37	0.933	C28—H48	0.959
C15—C16	1.389 (9)	C28—H49	0.959
C15—H38	0.929
P2—O1—C5	109.6 (13)	C15—C16—C17	122 (2)
O1—P2—N3	95.3 (8)	C15—C16—H39	119.0
O1—P2—O6	114.9 (9)	C17—C16—H39	119.0
N3—P2—O6	123.7 (9)	C16—C17—C18	120 (2)
O1—P2—C7	101.9 (8)	C16—C17—H40	120.2
N3—P2—C7	114.2 (9)	C18—C17—H40	120.1
O6—P2—C7	104.9 (10)	C17—C18—C13	119 (2)
P2—N3—C4	115.9 (13)	C17—C18—H41	120.7
P2—N3—C25	125.1 (14)	C13—C18—H41	120.3
C4—N3—C25	119.0 (17)	C4—C19—C20	117.6 (18)
N3—C4—C5	100.1 (15)	C4—C19—C24	127.6 (19)
N3—C4—C19	118.1 (17)	C20—C19—C24	114 (2)
C5—C4—C19	108.7 (17)	C19—C20—C21	125 (2)
N3—C4—H30	109.5	C19—C20—H42	117.6
C5—C4—H30	109.5	C21—C20—H42	117.2
C19—C4—H30	110.3	C20—C21—C22	116 (3)
C4—C5—O1	106.3 (16)	C20—C21—H43	122.3
C4—C5—C13	118.3 (16)	C22—C21—H43	122.1
O1—C5—C13	109.9 (17)	C21—C22—C23	124 (2)
C4—C5—H29	107.5	C21—C22—H44	118.2
O1—C5—H29	107.3	C23—C22—H44	117.8
C13—C5—H29	107.0	C22—C23—C24	115 (2)
P2—C7—F8	102.7 (13)	C22—C23—H45	122.7
P2—C7—C9	115.5 (14)	C24—C23—H45	122.0
F8—C7—C9	107.9 (17)	C23—C24—C19	125 (2)
P2—C7—C10	108.4 (14)	C23—C24—H46	117.6
F8—C7—C10	106.2 (17)	C19—C24—H46	117.2
C9—C7—C10	115.0 (18)	N3—C25—C26	109.1 (18)
C7—C9—H31	109.5	N3—C25—C27	109.9 (19)
C7—C9—H32	109.5	C26—C25—C27	108 (2)
H31—C9—H32	109.2	N3—C25—C28	107.5 (17)
C7—C9—H33	109.7	C26—C25—C28	109 (2)
H31—C9—H33	109.6	C27—C25—C28	113.6 (19)
H32—C9—H33	109.4	C25—C26—H53	109.1
C7—C10—O11	117 (2)	C25—C26—H54	110.1
C7—C10—C12	113 (2)	H53—C26—H54	109.5
O11—C10—C12	130 (3)	C25—C26—H55	109.1
C10—C12—H34	109.3	H53—C26—H55	109.4
C10—C12—H35	109.5	H54—C26—H55	109.6
H34—C12—H35	109.5	C25—C27—H50	109.3
C10—C12—H36	109.5	C25—C27—H51	109.8
H34—C12—H36	109.5	H50—C27—H51	109.4
H35—C12—H36	109.5	C25—C27—H52	109.7
C5—C13—C14	122.9 (16)	H50—C27—H52	109.2
C5—C13—C18	117.7 (18)	H51—C27—H52	109.4
C14—C13—C18	119 (2)	C25—C28—H47	110.5
C13—C14—C15	123 (2)	C25—C28—H48	109.1
C13—C14—H37	118.3	H47—C28—H48	109.3
C15—C14—H37	118.4	C25—C28—H49	108.8
C14—C15—C16	117 (2)	H47—C28—H49	109.6
C14—C15—H38	121.5	H48—C28—H49	109.6
C16—C15—H38	121.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H30···O6^i	0.98	2.22	3.18 (2)	163
C28—H48···O11^ii	0.96	2.71	3.57 (3)	151

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

(V) (2R,4R,5S)-3-tert-butyl-2-[(1R)-1-methyl-2-oxo- propyl]-4,5-diphenyl-[1,3,2]-oxazaphospholidine2-oxide

Crystal data

C22H28NO3P	F(000) = 824
Mr = 385.44	Dx = 1.225 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.109 (3) Å	θ = 6–11°
b = 14.047 (3) Å	µ = 0.15 mm^−1
c = 13.206 (6) Å	T = 175 K
β = 111.48 (3)°	Needle, translucent pale white
V = 2090.3 (12) Å^3	0.50 × 0.06 × 0.04 mm
Z = 4

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.018
Graphite monochromator	θmax = 22.0°, θmin = 2.2°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan ?	k = 0→14
Tmin = 0.84, Tmax = 0.92	l = −13→12
2836 measured reflections	3 standard reflections every 60 min
2561 independent reflections	intensity decay: 0.5%
1019 reflections with I > 2.0σ(I)

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.065	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 1.36 0.232 0.960
S = 1.14	(Δ/σ)max = 0.006
1019 reflections	Δρmax = 0.44 e Å^−3
244 parameters	Δρmin = −0.30 e Å^−3
0 restraints

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

	x	y	z	Uiso*/Ueq
O1	0.1346 (5)	0.2809 (4)	0.3581 (4)	0.0391
P2	0.1103 (2)	0.16993 (18)	0.3591 (2)	0.0407
N3	0.1662 (6)	0.1411 (4)	0.2664 (5)	0.0409
C4	0.2351 (7)	0.2219 (6)	0.2473 (6)	0.0371
C5	0.1687 (8)	0.3096 (6)	0.2692 (6)	0.0359
O6	0.1603 (5)	0.1267 (4)	0.4669 (5)	0.0571
C7	0.1780 (9)	0.0419 (7)	0.2290 (8)	0.0532
C8	0.2793 (16)	−0.0080 (9)	0.3124 (14)	0.1773
C9	0.188 (2)	0.0466 (9)	0.1231 (14)	0.1943
C10	0.0692 (14)	−0.0156 (8)	0.2208 (13)	0.1206
C11	−0.0519 (8)	0.1583 (6)	0.3063 (7)	0.0445
C12	−0.1133 (8)	0.2097 (7)	0.1988 (7)	0.0626
C13	−0.0941 (8)	0.1913 (8)	0.3973 (8)	0.0528
O14	−0.1316 (6)	0.2721 (6)	0.3943 (7)	0.0813
C15	−0.0911 (9)	0.1221 (7)	0.4827 (8)	0.0560
C16	0.3657 (8)	0.2233 (6)	0.3119 (7)	0.0402
C17	0.4442 (9)	0.2519 (6)	0.2630 (8)	0.0490
C18	0.5637 (10)	0.2615 (7)	0.3213 (10)	0.0594
C19	0.6091 (10)	0.2415 (7)	0.4306 (10)	0.0652
C20	0.5333 (10)	0.2100 (8)	0.4789 (9)	0.0662
C21	0.4142 (9)	0.2006 (5)	0.4235 (8)	0.0450
C22	0.2429 (8)	0.3995 (6)	0.2968 (7)	0.0403
C23	0.2729 (8)	0.4428 (6)	0.2180 (8)	0.0484
C24	0.3450 (8)	0.5227 (7)	0.2434 (8)	0.0521
C25	0.3845 (8)	0.5608 (7)	0.3463 (9)	0.0564
C26	0.3548 (9)	0.5180 (7)	0.4250 (8)	0.0609
C27	0.2825 (8)	0.4371 (7)	0.4003 (9)	0.0536
H28	0.3550	0.0276	0.3192	0.1674*
H29	0.2878	−0.0748	0.2848	0.1674*
H30	0.2699	−0.0117	0.3815	0.1674*
H31	0.2617	0.0855	0.1303	0.2534*
H32	0.1976	−0.0181	0.0962	0.2534*
H33	0.1176	0.0789	0.0704	0.2534*
H34	0.0721	−0.0830	0.1943	0.1491*
H35	−0.0042	0.0157	0.1640	0.1491*
H36	0.0560	−0.0183	0.2908	0.1491*
H37	−0.0828	0.1901	0.1414	0.0704*
H38	−0.0944	0.2820	0.2126	0.0704*
H39	−0.2011	0.2034	0.1716	0.0704*
H40	−0.0775	0.0880	0.2839	0.0608*
H44	0.0975	0.3268	0.1988	0.0520*
H45	0.2376	0.2170	0.1722	0.0492*
H46	0.3579	0.1768	0.4609	0.0504*
H47	0.5683	0.1906	0.5612	0.0794*
H48	0.6974	0.2543	0.4748	0.0826*
H49	0.6210	0.2808	0.2818	0.0699*
H50	0.4109	0.2663	0.1817	0.0638*
H51	0.2447	0.4147	0.1401	0.0540*
H52	0.3670	0.5561	0.1824	0.0606*
H53	0.4404	0.6173	0.3652	0.0683*
H54	0.3835	0.5462	0.5005	0.0635*
H55	0.2624	0.4041	0.4600	0.0613*
H43	−0.1375	0.0600	0.4475	0.0500*
H41	−0.1055	0.1545	0.5436	0.0500*
H42	−0.0070	0.1012	0.5207	0.0749*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.041 (4)	0.038 (4)	0.042 (3)	−0.005 (3)	0.019 (3)	−0.006 (3)
P2	0.0485 (17)	0.0396 (16)	0.0353 (15)	0.0072 (14)	0.0170 (12)	0.0023 (13)
N3	0.064 (5)	0.029 (5)	0.041 (4)	−0.010 (4)	0.032 (4)	−0.010 (4)
C4	0.047 (6)	0.035 (5)	0.032 (5)	−0.003 (5)	0.018 (5)	−0.011 (4)
C5	0.043 (6)	0.040 (6)	0.020 (5)	−0.013 (4)	0.006 (4)	0.002 (4)
O6	0.054 (4)	0.078 (5)	0.040 (4)	0.020 (3)	0.018 (3)	0.014 (3)
C7	0.070 (7)	0.038 (6)	0.069 (7)	−0.003 (5)	0.047 (6)	−0.007 (5)
C8	0.223 (19)	0.059 (9)	0.175 (17)	0.070 (11)	−0.015 (15)	−0.048 (10)
C9	0.44 (3)	0.052 (8)	0.193 (17)	−0.088 (14)	0.24 (2)	−0.072 (10)
C10	0.201 (16)	0.050 (8)	0.171 (14)	−0.029 (9)	0.138 (13)	−0.038 (9)
C11	0.054 (6)	0.036 (6)	0.050 (6)	−0.026 (5)	0.027 (5)	−0.009 (5)
C12	0.045 (6)	0.076 (8)	0.055 (7)	−0.019 (6)	0.005 (5)	0.015 (6)
C13	0.038 (6)	0.053 (7)	0.068 (8)	−0.010 (5)	0.020 (6)	0.003 (5)
O14	0.091 (6)	0.050 (5)	0.132 (7)	0.010 (5)	0.075 (6)	0.020 (5)
C15	0.063 (7)	0.059 (7)	0.055 (6)	−0.009 (5)	0.033 (6)	0.000 (5)
C16	0.046 (6)	0.032 (5)	0.053 (6)	0.007 (5)	0.030 (5)	−0.002 (5)
C17	0.045 (7)	0.044 (7)	0.053 (6)	0.002 (4)	0.012 (5)	−0.009 (5)
C18	0.056 (8)	0.060 (7)	0.075 (8)	0.007 (5)	0.040 (7)	−0.004 (6)
C19	0.052 (8)	0.061 (8)	0.076 (9)	0.015 (6)	0.016 (7)	−0.018 (7)
C20	0.044 (8)	0.085 (9)	0.064 (7)	0.011 (6)	0.012 (6)	−0.020 (6)
C21	0.058 (8)	0.041 (6)	0.042 (6)	0.009 (5)	0.025 (5)	0.008 (5)
C22	0.051 (6)	0.045 (6)	0.020 (5)	0.011 (5)	0.007 (5)	0.006 (5)
C23	0.060 (7)	0.036 (6)	0.043 (6)	−0.009 (5)	0.011 (5)	−0.008 (5)
C24	0.055 (7)	0.049 (7)	0.050 (7)	0.007 (5)	0.017 (5)	0.003 (6)
C25	0.052 (7)	0.041 (6)	0.074 (8)	−0.014 (5)	0.021 (6)	0.001 (6)
C26	0.072 (8)	0.053 (7)	0.044 (6)	−0.017 (6)	0.004 (6)	−0.015 (5)
C27	0.060 (7)	0.051 (7)	0.061 (7)	−0.006 (6)	0.036 (6)	−0.003 (6)

Geometric parameters (Å, º)

O1—P2	1.587 (6)	C12—H39	0.994
O1—C5	1.437 (9)	C13—O14	1.218 (10)
P2—N3	1.652 (7)	C13—C15	1.479 (12)
P2—O6	1.459 (6)	C15—H43	1.050
P2—C11	1.836 (9)	C15—H41	0.994
N3—C4	1.484 (10)	C15—H42	1.000
N3—C7	1.502 (11)	C16—C17	1.389 (11)
C4—C5	1.554 (11)	C16—C21	1.409 (12)
C4—C16	1.497 (11)	C17—C18	1.374 (13)
C4—H45	1.006	C17—H50	1.020
C5—C22	1.515 (11)	C18—C19	1.373 (13)
C5—H44	1.039	C18—H49	1.045
C7—C8	1.490 (16)	C19—C20	1.368 (13)
C7—C9	1.448 (15)	C19—H48	1.029
C7—C10	1.515 (14)	C20—C21	1.363 (12)
C8—H28	1.019	C20—H47	1.049
C8—H29	1.026	C21—H46	1.034
C8—H30	0.962	C22—C23	1.365 (11)
C9—H31	1.024	C22—C27	1.377 (12)
C9—H32	0.999	C23—C24	1.386 (12)
C9—H33	0.988	C23—H51	1.036
C10—H34	1.015	C24—C25	1.374 (13)
C10—H35	1.028	C24—H52	1.047
C10—H36	0.993	C25—C26	1.357 (13)
C11—C12	1.522 (11)	C25—H53	1.013
C11—C13	1.540 (13)	C26—C27	1.398 (12)
C11—H40	1.044	C26—H54	1.009
C12—H37	0.996	C27—H55	1.019
C12—H38	1.042
P2—O1—C5	113.1 (5)	C11—C12—H37	112.8
O1—P2—N3	96.1 (3)	C11—C12—H38	107.4
O1—P2—O6	113.9 (4)	H37—C12—H38	106.5
N3—P2—O6	119.0 (4)	C11—C12—H39	112.8
O1—P2—C11	105.1 (4)	H37—C12—H39	110.3
N3—P2—C11	111.6 (4)	H38—C12—H39	106.7
O6—P2—C11	109.7 (4)	C11—C13—O14	118.8 (9)
P2—N3—C4	110.3 (5)	C11—C13—C15	118.3 (9)
P2—N3—C7	125.8 (5)	O14—C13—C15	122.8 (10)
C4—N3—C7	121.8 (6)	C13—C15—H43	110.4
N3—C4—C5	102.3 (6)	C13—C15—H41	110.7
N3—C4—C16	117.1 (8)	H43—C15—H41	121.0
C5—C4—C16	113.2 (7)	C13—C15—H42	108.1
N3—C4—H45	109.7	H43—C15—H42	105.1
C5—C4—H45	116.3	H41—C15—H42	100.1
C16—C4—H45	99.0	C4—C16—C17	119.9 (8)
C4—C5—O1	104.7 (6)	C4—C16—C21	122.8 (8)
C4—C5—C22	113.8 (7)	C17—C16—C21	117.2 (9)
O1—C5—C22	111.0 (6)	C16—C17—C18	121.8 (9)
C4—C5—H44	109.5	C16—C17—H50	118.2
O1—C5—H44	113.9	C18—C17—H50	120.0
C22—C5—H44	104.2	C17—C18—C19	120.2 (10)
N3—C7—C8	110.1 (9)	C17—C18—H49	120.1
N3—C7—C9	109.1 (8)	C19—C18—H49	119.6
C8—C7—C9	113.5 (12)	C18—C19—C20	118.5 (10)
N3—C7—C10	109.5 (7)	C18—C19—H48	119.6
C8—C7—C10	105.2 (11)	C20—C19—H48	121.8
C9—C7—C10	109.4 (12)	C19—C20—C21	122.7 (11)
C7—C8—H28	107.8	C19—C20—H47	118.8
C7—C8—H29	109.3	C21—C20—H47	118.5
H28—C8—H29	106.0	C16—C21—C20	119.5 (9)
C7—C8—H30	112.0	C16—C21—H46	118.5
H28—C8—H30	111.0	C20—C21—H46	122.0
H29—C8—H30	110.4	C5—C22—C23	119.2 (8)
C7—C9—H31	108.2	C5—C22—C27	121.3 (8)
C7—C9—H32	111.4	C23—C22—C27	119.5 (9)
H31—C9—H32	107.7	C22—C23—C24	119.8 (9)
C7—C9—H33	110.4	C22—C23—H51	120.3
H31—C9—H33	108.5	C24—C23—H51	119.9
H32—C9—H33	110.6	C23—C24—C25	121.0 (10)
C7—C10—H34	112.5	C23—C24—H52	119.4
C7—C10—H35	108.7	C25—C24—H52	119.5
H34—C10—H35	106.1	C24—C25—C26	119.4 (9)
C7—C10—H36	112.6	C24—C25—H53	120.5
H34—C10—H36	108.8	C26—C25—H53	120.0
H35—C10—H36	107.7	C25—C26—C27	120.0 (9)
P2—C11—C12	113.7 (6)	C25—C26—H54	119.4
P2—C11—C13	106.9 (6)	C27—C26—H54	120.6
C12—C11—C13	113.4 (8)	C26—C27—C22	120.3 (9)
P2—C11—H40	110.9	C26—C27—H55	119.7
C12—C11—H40	101.1	C22—C27—H55	119.9
C13—C11—H40	110.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H51···O6^i	1.04	2.21	3.240 (12)	170
C10—H34···O14^ii	1.01	2.58	3.552 (16)	161

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

(VI) (2R,4S,5R)-3-tert-butyl-2-benzyl-4,5-diphenyl- [1,3,2]-oxazaphospholidine2-oxide

Crystal data

C25H28NO2P	F(000) = 864
Mr = 405.48	Dx = 1.103 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23 reflections
a = 10.284 (2) Å	θ = 10.1–16.2°
b = 21.262 (4) Å	µ = 0.13 mm^−1
c = 12.768 (2) Å	T = 175 K
β = 119.04 (2)°	Needle, translucent pale white
V = 2440.9 (9) Å^3	0.37 × 0.07 × 0.04 mm
Z = 4

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.04
Graphite monochromator	θmax = 22.0°, θmin = 2.1°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan ?	k = −21→0
Tmin = 0.81, Tmax = 0.91	l = −9→12
2619 measured reflections	3 standard reflections every 0 reflections
2576 independent reflections	intensity decay: 0.4%
1037 reflections with I > 2.0σ(I)

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.091	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 17.0 7.24 12.9 7.66 1.45
S = 1.16	(Δ/σ)max = 0.000081
1037 reflections	Δρmax = 0.46 e Å^−3
132 parameters	Δρmin = −0.52 e Å^−3
19 restraints

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

	x	y	z	Uiso*/Ueq
O1	0.8002 (8)	0.0350 (3)	0.6399 (8)	0.0321
P2	0.6633 (3)	0.08665 (14)	0.5753 (3)	0.0246
N3	0.7835 (10)	0.1483 (4)	0.6371 (8)	0.026 (3)*
C4	0.9529 (12)	0.1281 (5)	0.7093 (8)	0.025 (3)*
C5	0.9364 (12)	0.0603 (5)	0.6500 (11)	0.023 (3)*
O6	0.5496 (8)	0.0837 (4)	0.4280 (7)	0.0317
C7	0.7392 (12)	0.2114 (5)	0.5688 (10)	0.022 (3)*
C8	0.8529 (13)	0.2599 (5)	0.6696 (11)	0.030 (3)*
C9	0.7382 (14)	0.2116 (6)	0.4434 (12)	0.038 (3)*
C10	0.5789 (12)	0.2293 (6)	0.5374 (11)	0.030 (3)*
C11	0.5700 (12)	0.0688 (5)	0.6634 (11)	0.027 (3)*
C12	0.4261 (11)	0.1119 (5)	0.6198 (8)	0.024 (3)*
C13	0.2991 (10)	0.1080 (5)	0.5022 (9)	0.026 (3)*
C14	0.1754 (13)	0.1481 (5)	0.4626 (11)	0.043 (4)*
C15	0.1901 (13)	0.1906 (6)	0.5526 (9)	0.039 (4)*
C16	0.3141 (11)	0.1926 (6)	0.6716 (10)	0.036 (3)*
C17	0.4374 (12)	0.1522 (5)	0.7126 (10)	0.033 (3)*
C18	1.0752 (12)	0.0169 (5)	0.7358 (9)	0.026 (3)*
C19	1.1034 (13)	−0.0132 (5)	0.8432 (9)	0.032 (3)*
C20	1.2290 (11)	−0.0492 (5)	0.9196 (11)	0.038 (4)*
C21	1.3397 (14)	−0.0548 (6)	0.8862 (11)	0.045 (4)*
C22	1.3141 (13)	−0.0253 (6)	0.7786 (10)	0.046 (4)*
C23	1.1868 (11)	0.0107 (6)	0.7037 (11)	0.035 (3)*
C24	1.0479 (10)	0.1345 (5)	0.8555 (8)	0.021 (3)*
C25	0.9904 (13)	0.1347 (5)	0.9367 (9)	0.032 (3)*
C26	1.0755 (11)	0.1353 (5)	1.0652 (9)	0.033 (3)*
C27	1.2335 (11)	0.1358 (6)	1.1331 (12)	0.038 (4)*
C28	1.2958 (15)	0.1383 (6)	1.0567 (10)	0.048 (4)*
C29	1.2069 (10)	0.1369 (5)	0.9282 (9)	0.030 (3)*
H57	0.9276	0.0640	0.5697	0.0312*
H58	1.0041	0.1536	0.6774	0.0302*
H32	0.8323	0.3023	0.6390	0.0386*
H31	0.9533	0.2497	0.6898	0.0386*
H30	0.8445	0.2581	0.7414	0.0386*
H37	0.7112	0.2524	0.4065	0.0468*
H38	0.8356	0.2013	0.4563	0.0468*
H36	0.6690	0.1810	0.3899	0.0468*
H35	0.5541	0.2691	0.4963	0.0369*
H33	0.5725	0.2324	0.6101	0.0369*
H34	0.5105	0.1980	0.4857	0.0369*
H51	0.6384	0.0752	0.7478	0.0344*
H50	0.5391	0.0251	0.6489	0.0344*
H56	0.2976	0.0778	0.4490	0.0327*
H55	0.0936	0.1466	0.3859	0.0492*
H53	0.3144	0.2221	0.7255	0.0440*
H52	0.5153	0.1520	0.7902	0.0385*
H45	1.0310	−0.0086	0.8661	0.0432*
H46	1.2384	−0.0683	0.9884	0.0504*
H47	1.4266	−0.0769	0.9330	0.0559*
H49	1.1766	0.0301	0.6344	0.0426*
H39	0.8878	0.1344	0.9030	0.0409*
H41	1.2890	0.1348	1.2161	0.0452*
H43	1.3984	0.1410	1.0908	0.0538*
H40	1.0233	0.1355	1.1075	0.0389*
H44	1.2581	0.1378	0.8849	0.0391*
H48	1.3863	−0.0300	0.7553	0.0568*
H54	0.1132	0.2190	0.5326	0.0515*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.020 (5)	0.010 (4)	0.059 (6)	−0.004 (3)	0.013 (5)	−0.002 (4)
P2	0.0208 (18)	0.0154 (15)	0.036 (2)	0.0010 (16)	0.0123 (17)	−0.0005 (17)
O6	0.040 (5)	0.028 (5)	0.035 (6)	0.000 (4)	0.024 (5)	−0.002 (4)

Geometric parameters (Å, º)

O1—P2	1.655 (8)	C13—H56	0.929
O1—C5	1.447 (13)	C14—C15	1.413 (9)
P2—N3	1.710 (10)	C14—H55	0.931
P2—O6	1.665 (9)	C15—C16	1.434 (9)
P2—C11	1.837 (11)	C15—H54	0.927
N3—C4	1.585 (14)	C16—C17	1.406 (9)
N3—C7	1.542 (14)	C16—H53	0.930
C4—C5	1.599 (15)	C17—H52	0.923
C4—C24	1.640 (9)	C18—C19	1.409 (9)
C4—H58	0.972	C18—C23	1.400 (9)
C5—C18	1.604 (15)	C19—C20	1.409 (9)
C5—H57	0.987	C19—H45	0.928
C7—C8	1.621 (15)	C20—C21	1.401 (9)
C7—C9	1.597 (17)	C20—H46	0.929
C7—C10	1.544 (15)	C21—C22	1.413 (9)
C8—H32	0.964	C21—H47	0.927
C8—H31	0.960	C22—C23	1.413 (9)
C8—H30	0.962	C22—H48	0.930
C9—H37	0.960	C23—H49	0.936
C9—H38	0.958	C24—C25	1.420 (9)
C9—H36	0.961	C24—C29	1.436 (9)
C10—H35	0.962	C25—C26	1.437 (9)
C10—H33	0.964	C25—H39	0.927
C10—H34	0.960	C26—C27	1.423 (9)
C11—C12	1.594 (14)	C26—H40	0.928
C11—H51	0.969	C27—C28	1.404 (9)
C11—H50	0.969	C27—H41	0.928
C12—C13	1.437 (9)	C28—C29	1.440 (9)
C12—C17	1.420 (9)	C28—H43	0.928
C13—C14	1.405 (9)	C29—H44	0.931
P2—O1—C5	110.5 (6)	C11—C12—C17	111.7 (8)
O1—P2—N3	91.6 (4)	C13—C12—C17	124.8 (10)
O1—P2—O6	120.0 (5)	C12—C13—C14	123.1 (10)
N3—P2—O6	120.2 (5)	C12—C13—H56	119.2
O1—P2—C11	97.3 (5)	C14—C13—H56	117.6
N3—P2—C11	110.6 (5)	C13—C14—C15	112.0 (11)
O6—P2—C11	113.3 (5)	C13—C14—H55	123.8
P2—N3—C4	113.9 (7)	C15—C14—H55	124.1
P2—N3—C7	117.2 (7)	C14—C15—C16	124.7 (12)
C4—N3—C7	120.3 (8)	C14—C15—H54	116.9
N3—C4—C5	97.8 (7)	C16—C15—H54	118.3
N3—C4—C24	121.3 (8)	C15—C16—C17	123.6 (12)
C5—C4—C24	118.8 (9)	C15—C16—H53	119.0
N3—C4—H58	105.8	C17—C16—H53	117.3
C5—C4—H58	105.0	C12—C17—C16	111.4 (10)
C24—C4—H58	106.6	C12—C17—H52	124.8
C4—C5—O1	104.6 (8)	C16—C17—H52	123.8
C4—C5—C18	109.9 (9)	C5—C18—C19	128.3 (9)
O1—C5—C18	110.5 (9)	C5—C18—C23	116.0 (9)
C4—C5—H57	110.7	C19—C18—C23	115.5 (11)
O1—C5—H57	110.0	C18—C19—C20	127.4 (12)
C18—C5—H57	111.0	C18—C19—H45	116.2
N3—C7—C8	101.7 (9)	C20—C19—H45	116.4
N3—C7—C9	115.3 (9)	C19—C20—C21	116.2 (12)
C8—C7—C9	116.4 (9)	C19—C20—H46	122.1
N3—C7—C10	110.3 (9)	C21—C20—H46	121.7
C8—C7—C10	108.5 (9)	C20—C21—C22	117.6 (12)
C9—C7—C10	104.6 (9)	C20—C21—H47	121.2
C7—C8—H32	109.9	C22—C21—H47	121.3
C7—C8—H31	109.7	C21—C22—C23	124.9 (12)
H32—C8—H31	108.5	C21—C22—H48	117.5
C7—C8—H30	111.5	C23—C22—H48	117.6
H32—C8—H30	108.6	C22—C23—C18	118.3 (11)
H31—C8—H30	108.5	C22—C23—H49	121.4
C7—C9—H37	110.7	C18—C23—H49	120.2
C7—C9—H38	109.2	C4—C24—C25	127.0 (9)
H37—C9—H38	108.7	C4—C24—C29	126.9 (9)
C7—C9—H36	110.6	C25—C24—C29	106.0 (9)
H37—C9—H36	108.9	C24—C25—C26	126.5 (11)
H38—C9—H36	108.6	C24—C25—H39	116.5
C7—C10—H35	109.0	C26—C25—H39	117.0
C7—C10—H33	109.2	C25—C26—C27	125.3 (12)
H35—C10—H33	110.0	C25—C26—H40	117.5
C7—C10—H34	109.9	C27—C26—H40	117.2
H35—C10—H34	108.8	C26—C27—C28	110.4 (12)
H33—C10—H34	109.8	C26—C27—H41	125.7
P2—C11—C12	109.8 (7)	C28—C27—H41	123.9
P2—C11—H51	109.9	C27—C28—C29	122.6 (13)
C12—C11—H51	110.9	C27—C28—H43	118.4
P2—C11—H50	107.6	C29—C28—H43	119.0
C12—C11—H50	108.7	C28—C29—C24	129.1 (11)
H51—C11—H50	109.9	C28—C29—H44	116.6
C11—C12—C13	123.4 (9)	C24—C29—H44	114.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H50···O6^i	0.97	2.51	3.463 (14)	169
C13—H56···O1^i	0.93	2.64	3.432 (13)	143

Symmetry code: (i) −x+1, −y, −z+1.

(VII) (2R,3S,5S)-3,5-diphenyl-2-(4-methoxyphenyl)- [1,4,2]-oxazaphosphorinane2-oxide

Crystal data

C22H22NO3P	F(000) = 400
Mr = 379.40	Dx = 1.316 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5384 reflections
a = 10.0104 (3) Å	θ = 3.0–32.2°
b = 8.1056 (1) Å	µ = 0.17 mm^−1
c = 12.5372 (3) Å	T = 175 K
β = 109.717 (5)°	Prism, translucent pale white
V = 957.63 (5) Å^3	0.32 × 0.30 × 0.20 mm
Z = 2

Data collection

Oxford Diffraction XCALIBUR diffractometer	3438 reflections with I > 2.0σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.028
Graphite monochromator	θmax = 32.2°, θmin = 3.3°
ω scans	h = −14→14
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −11→12
Tmin = 0.952, Tmax = 0.967	l = −18→18
12688 measured reflections	Standard reflections: 4 frames; every 25 frames reflections
5435 independent reflections	intensity decay: none

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 18.4 -27.6 15.3 -5.81
wR(F^2) = 0.046	(Δ/σ)max = 0.000432
S = 1.11	Δρmax = 0.23 e Å^−3
3438 reflections	Δρmin = −0.31 e Å^−3
245 parameters	Absolute structure: Flack (1983), 2104 Friedel-pairs
1 restraint	Absolute structure parameter: 0.18 (12)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.0586 (2)	0.3623 (3)	0.70204 (17)	0.0324
P2	0.17060 (7)	0.29948 (12)	0.64536 (6)	0.0264
C3	0.0934 (3)	0.1060 (4)	0.5795 (2)	0.0249
N4	0.0470 (2)	0.0104 (3)	0.66095 (18)	0.0252
C5	−0.0662 (3)	0.0962 (4)	0.6903 (2)	0.0277
C6	−0.0044 (3)	0.2494 (4)	0.7600 (3)	0.0344
O7	0.1877 (2)	0.4236 (3)	0.56487 (17)	0.0359
C8	0.3354 (3)	0.2597 (3)	0.7574 (2)	0.0232
C9	0.4500 (3)	0.3598 (4)	0.7613 (2)	0.0275
C10	0.5794 (3)	0.3441 (4)	0.8479 (2)	0.0306
C11	0.5949 (3)	0.2265 (4)	0.9319 (2)	0.0292
C12	0.4836 (3)	0.1235 (4)	0.9289 (2)	0.0286
C13	0.3545 (3)	0.1402 (3)	0.8415 (2)	0.0282
O14	0.7256 (2)	0.2236 (3)	1.01393 (18)	0.0428
C15	0.7473 (4)	0.1052 (5)	1.1036 (3)	0.0508
C16	−0.1243 (3)	−0.0169 (4)	0.7597 (2)	0.0299
C17	−0.2701 (3)	−0.0354 (4)	0.7342 (3)	0.0381
C18	−0.3220 (4)	−0.1385 (5)	0.8005 (3)	0.0487
C19	−0.2307 (4)	−0.2228 (5)	0.8906 (3)	0.0516
C20	−0.0846 (4)	−0.2057 (6)	0.9169 (3)	0.0466
C21	−0.0332 (3)	−0.1028 (4)	0.8517 (3)	0.0370
C22	0.1987 (3)	0.0132 (4)	0.5395 (2)	0.0250
C23	0.2648 (3)	−0.1298 (4)	0.5915 (2)	0.0312
C24	0.3631 (3)	−0.2097 (5)	0.5538 (3)	0.0385
C25	0.3984 (3)	−0.1446 (4)	0.4645 (3)	0.0369
C26	0.3319 (3)	−0.0031 (4)	0.4109 (3)	0.0356
C27	0.2325 (3)	0.0744 (4)	0.4476 (2)	0.0316
H28	−0.0828	0.3070	0.7754	0.0439*
H29	0.0675	0.2139	0.8315	0.0439*
H30	−0.1435	0.1271	0.6199	0.0330*
H31	0.0165	−0.0880	0.6225	0.0500*
H32	0.0103	0.1377	0.5140	0.0327*
H33	0.2783	0.0690	0.8386	0.0344*
H34	0.4948	0.0418	0.9851	0.0348*
H35	0.6549	0.4141	0.8493	0.0364*
H36	0.4385	0.4410	0.7048	0.0340*
H37	0.6820	0.1291	1.1433	0.0564*
H38	0.8438	0.1168	1.1543	0.0564*
H39	0.7338	−0.0069	1.0728	0.0564*
H40	−0.3320	0.0211	0.6727	0.0459*
H41	−0.4205	−0.1479	0.7832	0.0656*
H42	−0.2664	−0.2917	0.9347	0.0614*
H43	−0.0210	−0.2639	0.9787	0.0601*
H44	0.0646	−0.0899	0.8696	0.0441*
H45	0.2443	−0.1731	0.6534	0.0366*
H46	0.4039	−0.3074	0.5883	0.0486*
H47	0.4680	−0.1983	0.4413	0.0471*
H48	0.3538	0.0409	0.3489	0.0466*
H49	0.1866	0.1707	0.4106	0.0395*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (10)	0.0273 (10)	0.0379 (11)	0.0056 (9)	0.0094 (9)	−0.0018 (9)
P2	0.0260 (3)	0.0255 (3)	0.0239 (3)	0.0013 (4)	0.0031 (2)	0.0023 (3)
C3	0.0255 (13)	0.0306 (15)	0.0185 (11)	−0.0032 (11)	0.0073 (10)	−0.0003 (10)
N4	0.0274 (12)	0.0297 (12)	0.0217 (11)	−0.0031 (10)	0.0122 (9)	−0.0037 (9)
C5	0.0211 (13)	0.0363 (16)	0.0234 (13)	0.0019 (12)	0.0046 (10)	−0.0010 (12)
C6	0.0340 (15)	0.0398 (18)	0.0292 (14)	0.0029 (13)	0.0104 (12)	−0.0019 (12)
O7	0.0367 (12)	0.0344 (11)	0.0317 (11)	0.0001 (10)	0.0052 (9)	0.0100 (9)
C8	0.0245 (12)	0.0247 (15)	0.0184 (11)	0.0004 (10)	0.0048 (9)	−0.0027 (9)
C9	0.0294 (13)	0.0276 (13)	0.0258 (13)	−0.0014 (12)	0.0097 (11)	0.0053 (11)
C10	0.0248 (13)	0.0321 (16)	0.0343 (14)	−0.0052 (11)	0.0093 (11)	0.0066 (11)
C11	0.0263 (14)	0.0318 (15)	0.0245 (13)	0.0003 (12)	0.0022 (10)	−0.0013 (11)
C12	0.0300 (14)	0.0282 (15)	0.0263 (13)	−0.0028 (12)	0.0077 (11)	0.0068 (11)
C13	0.0293 (15)	0.0251 (14)	0.0273 (14)	−0.0062 (12)	0.0058 (11)	0.0023 (11)
O14	0.0319 (12)	0.0490 (14)	0.0374 (12)	−0.0085 (11)	−0.0016 (9)	0.0168 (11)
C15	0.049 (2)	0.053 (2)	0.0354 (17)	−0.0080 (18)	−0.0063 (15)	0.0194 (16)
C16	0.0238 (13)	0.0403 (17)	0.0277 (14)	−0.0009 (12)	0.0114 (11)	−0.0071 (12)
C17	0.0246 (14)	0.049 (2)	0.0413 (17)	−0.0015 (14)	0.0119 (12)	−0.0060 (15)
C18	0.0351 (17)	0.067 (2)	0.051 (2)	−0.0172 (17)	0.0226 (15)	−0.0189 (18)
C19	0.058 (2)	0.062 (3)	0.0475 (18)	−0.017 (2)	0.0346 (17)	−0.0074 (18)
C20	0.0529 (19)	0.057 (2)	0.0348 (15)	0.001 (2)	0.0210 (14)	0.0038 (19)
C21	0.0274 (15)	0.055 (2)	0.0309 (15)	−0.0008 (14)	0.0123 (12)	0.0044 (14)
C22	0.0262 (13)	0.0278 (13)	0.0207 (12)	−0.0046 (12)	0.0077 (10)	−0.0039 (10)
C23	0.0319 (14)	0.0341 (15)	0.0300 (14)	0.0013 (13)	0.0137 (11)	0.0068 (12)
C24	0.0398 (15)	0.0362 (16)	0.0426 (16)	0.0095 (17)	0.0180 (13)	0.0048 (17)
C25	0.0365 (16)	0.0368 (16)	0.0431 (17)	−0.0012 (14)	0.0209 (14)	−0.0065 (14)
C26	0.0403 (17)	0.0374 (17)	0.0354 (16)	−0.0070 (14)	0.0213 (13)	−0.0020 (13)
C27	0.0376 (16)	0.0303 (15)	0.0289 (14)	−0.0028 (13)	0.0140 (12)	0.0017 (12)

Geometric parameters (Å, º)

O1—P2	1.600 (2)	O14—C15	1.438 (4)
O1—C6	1.440 (4)	C15—H37	0.965
P2—C3	1.818 (3)	C15—H38	0.965
P2—O7	1.475 (2)	C15—H39	0.978
P2—C8	1.799 (3)	C16—C17	1.393 (4)
C3—N4	1.476 (3)	C16—C21	1.392 (4)
C3—C22	1.512 (4)	C17—C18	1.396 (5)
C3—H32	0.986	C17—H40	0.931
N4—C5	1.478 (4)	C18—C19	1.372 (6)
N4—H31	0.928	C18—H41	0.938
C5—C6	1.524 (4)	C19—C20	1.394 (5)
C5—C16	1.509 (4)	C19—H42	0.937
C5—H30	0.990	C20—C21	1.383 (5)
C6—H28	0.987	C20—H43	0.947
C6—H29	0.984	C21—H44	0.933
C8—C9	1.393 (4)	C22—C23	1.384 (4)
C8—C13	1.397 (4)	C22—C27	1.397 (4)
C9—C10	1.387 (4)	C23—C24	1.388 (4)
C9—H36	0.945	C23—H45	0.935
C10—C11	1.390 (4)	C24—C25	1.387 (4)
C10—H35	0.941	C24—H46	0.929
C11—C12	1.382 (4)	C25—C26	1.382 (5)
C11—O14	1.365 (3)	C25—H47	0.947
C12—C13	1.390 (4)	C26—C27	1.381 (4)
C12—H34	0.946	C26—H48	0.945
C13—H33	0.948	C27—H49	0.944
P2—O1—C6	120.91 (19)	C12—C13—H33	119.6
O1—P2—C3	102.82 (12)	C11—O14—C15	117.0 (3)
O1—P2—O7	110.31 (13)	O14—C15—H37	108.6
C3—P2—O7	114.03 (13)	O14—C15—H38	107.7
O1—P2—C8	107.80 (12)	H37—C15—H38	110.0
C3—P2—C8	109.70 (12)	O14—C15—H39	110.3
O7—P2—C8	111.67 (13)	H37—C15—H39	111.2
P2—C3—N4	108.90 (17)	H38—C15—H39	108.9
P2—C3—C22	110.02 (18)	C5—C16—C17	120.7 (3)
N4—C3—C22	112.7 (2)	C5—C16—C21	120.6 (3)
P2—C3—H32	105.3	C17—C16—C21	118.7 (3)
N4—C3—H32	109.8	C16—C17—C18	120.0 (3)
C22—C3—H32	109.9	C16—C17—H40	119.4
C3—N4—C5	111.8 (2)	C18—C17—H40	120.7
C3—N4—H31	102.5	C17—C18—C19	120.7 (3)
C5—N4—H31	112.8	C17—C18—H41	119.0
N4—C5—C6	109.2 (2)	C19—C18—H41	120.3
N4—C5—C16	109.6 (2)	C18—C19—C20	120.0 (3)
C6—C5—C16	109.0 (2)	C18—C19—H42	120.2
N4—C5—H30	109.3	C20—C19—H42	119.9
C6—C5—H30	110.4	C19—C20—C21	119.4 (3)
C16—C5—H30	109.3	C19—C20—H43	120.5
C5—C6—O1	113.0 (2)	C21—C20—H43	120.2
C5—C6—H28	107.6	C16—C21—C20	121.4 (3)
O1—C6—H28	108.1	C16—C21—H44	119.0
C5—C6—H29	108.3	C20—C21—H44	119.6
O1—C6—H29	109.6	C3—C22—C23	122.4 (2)
H28—C6—H29	110.2	C3—C22—C27	119.1 (3)
P2—C8—C9	116.75 (19)	C23—C22—C27	118.4 (3)
P2—C8—C13	124.7 (2)	C22—C23—C24	120.8 (3)
C9—C8—C13	118.5 (2)	C22—C23—H45	120.1
C8—C9—C10	120.9 (2)	C24—C23—H45	119.1
C8—C9—H36	119.3	C23—C24—C25	120.0 (3)
C10—C9—H36	119.7	C23—C24—H46	119.4
C9—C10—C11	119.5 (3)	C25—C24—H46	120.6
C9—C10—H35	119.5	C24—C25—C26	119.8 (3)
C11—C10—H35	121.0	C24—C25—H47	119.2
C10—C11—C12	120.7 (2)	C26—C25—H47	121.1
C10—C11—O14	114.6 (3)	C25—C26—C27	119.9 (3)
C12—C11—O14	124.7 (3)	C25—C26—H48	120.4
C11—C12—C13	119.3 (3)	C27—C26—H48	119.7
C11—C12—H34	120.7	C22—C27—C26	121.1 (3)
C13—C12—H34	120.0	C22—C27—H49	119.1
C8—C13—C12	121.1 (3)	C26—C27—H49	119.9
C8—C13—H33	119.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H31···O7^i	0.93	2.54	3.089 (3)	118
C3—H32···O7^i	0.99	2.57	3.153 (4)	118
C21—H44···O14^ii	0.93	2.60	3.286 (4)	131

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

(VIII) (2S,3S,5S)-2,3,5-triphenyl-[1,4,2]-oxazaphosphorinane 2-oxide

Crystal data

C21H20NO2P	F(000) = 736
Mr = 349.37	Dx = 1.184 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 0 reflections
a = 5.6212 (6) Å	θ = 0–0°
b = 25.714 (2) Å	µ = 0.15 mm^−1
c = 13.561 (2) Å	T = 175 K
V = 1960.2 (4) Å^3	Needle, translucent pale white
Z = 4	0.33 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	6347 independent reflections
Radiation source: Enhance (Mo) X-ray Source	496 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.203
Detector resolution: 8.4205 pixels mm^-1	θmax = 32.5°, θmin = 2.8°
ω scans	h = −8→7
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −37→38
Tmin = 0.91, Tmax = 0.99	l = −20→19
33616 measured reflections

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.131	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 11.7 3.40 8.76 4.60 0.792
wR(F^2) = 0.119	(Δ/σ)max = 0.000049
S = 1.00	Δρmax = 1.86 e Å^−3
496 reflections	Δρmin = −0.51 e Å^−3
87 parameters	Absolute structure: Flack (1983), 2610 Friedel-pairs
6 restraints	Absolute structure parameter: 0.0 (15)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.284 (3)	0.2630 (8)	0.093 (2)	0.038 (7)*
P2	0.360 (2)	0.2893 (4)	0.1912 (9)	0.040 (3)*
C3	0.152 (7)	0.3456 (12)	0.203 (3)	0.029 (9)*
N4	0.196 (4)	0.3761 (11)	0.097 (3)	0.042 (9)*
C5	0.150 (8)	0.3409 (12)	0.014 (2)	0.038 (10)*
C6	0.305 (6)	0.2923 (14)	0.001 (2)	0.037 (11)*
O7	0.612 (4)	0.3030 (7)	0.2028 (16)	0.034 (7)*
C8	0.171 (7)	0.3688 (13)	−0.086 (3)	0.048 (5)*
C9	−0.021 (8)	0.3699 (14)	−0.152 (3)	0.048 (5)*
C10	−0.003 (8)	0.4002 (14)	−0.236 (2)	0.048 (5)*
C11	0.199 (7)	0.4324 (16)	−0.263 (3)	0.048 (5)*
C12	0.384 (7)	0.4341 (13)	−0.186 (3)	0.048 (5)*
C13	0.355 (7)	0.4047 (12)	−0.103 (3)	0.048 (5)*
C14	0.194 (6)	0.3792 (15)	0.287 (3)	0.038 (5)*
C15	0.394 (6)	0.4102 (13)	0.286 (2)	0.037 (5)*
C16	0.433 (6)	0.4410 (13)	0.374 (2)	0.038 (5)*
C17	0.248 (6)	0.4412 (14)	0.439 (3)	0.038 (5)*
C18	0.060 (6)	0.4115 (14)	0.433 (2)	0.037 (5)*
C19	0.036 (7)	0.3810 (13)	0.357 (3)	0.038 (5)*
C20	0.265 (5)	0.2455 (14)	0.283 (2)	0.041 (5)*
C21	0.050 (5)	0.2184 (11)	0.285 (2)	0.041 (5)*
C22	−0.005 (6)	0.1824 (12)	0.358 (2)	0.041 (5)*
C23	0.131 (6)	0.1807 (13)	0.444 (2)	0.041 (5)*
C24	0.349 (6)	0.2066 (13)	0.444 (2)	0.041 (5)*
C25	0.409 (6)	0.2392 (12)	0.365 (2)	0.041 (5)*
H26	0.2503	0.2720	−0.0543	0.0390*
H27	0.4706	0.3019	−0.0088	0.0390*
H28	−0.0149	0.3285	0.0193	0.0490*
H29	0.2283	0.4088	0.0941	0.0450*
H30	−0.0113	0.3321	0.2057	0.0350*
H31	−0.1553	0.3499	−0.1405	0.0600*
H32	−0.1300	0.3992	−0.2796	0.0600*
H33	0.2090	0.4507	−0.3223	0.0600*
H34	0.5179	0.4550	−0.1937	0.0600*
H35	0.4707	0.4076	−0.0549	0.0600*
H36	0.5028	0.4099	0.2343	0.0600*
H37	0.5697	0.4608	0.3837	0.0600*
H38	0.2578	0.4635	0.4927	0.0600*
H39	−0.0550	0.4127	0.4820	0.0600*
H40	−0.0980	0.3599	0.3536	0.0600*
H41	−0.0606	0.2245	0.2356	0.0600*
H42	−0.1314	0.1595	0.3499	0.0600*
H43	0.0779	0.1629	0.4994	0.0600*
H44	0.4551	0.2021	0.4956	0.0600*
H45	0.5517	0.2576	0.3684	0.0600*

Geometric parameters (Å, º)

O1—P2	1.56 (3)	C12—H34	0.930
O1—C6	1.45 (4)	C13—H35	0.931
P2—C3	1.87 (3)	C14—C15	1.38 (4)
P2—O7	1.46 (2)	C14—C19	1.30 (4)
P2—C20	1.76 (3)	C15—C16	1.44 (4)
C3—N4	1.66 (5)	C15—H36	0.932
C3—C14	1.45 (5)	C16—C17	1.36 (4)
C3—H30	0.983	C16—H37	0.931
N4—C5	1.46 (4)	C17—C18	1.31 (4)
N4—H29	0.860	C17—H38	0.932
C5—C6	1.53 (4)	C18—C19	1.29 (4)
C5—C8	1.54 (5)	C18—H39	0.931
C5—H28	0.984	C19—H40	0.929
C6—H26	0.969	C20—C21	1.394 (10)
C6—H27	0.970	C20—C25	1.395 (10)
C8—C9	1.41 (5)	C21—C22	1.389 (10)
C8—C13	1.40 (4)	C21—H41	0.929
C9—C10	1.38 (4)	C22—C23	1.392 (10)
C9—H31	0.930	C22—H42	0.929
C10—C11	1.45 (5)	C23—C24	1.396 (10)
C10—H32	0.926	C23—H43	0.934
C11—C12	1.48 (5)	C24—C25	1.392 (10)
C11—H33	0.929	C24—H44	0.929
C12—C13	1.36 (4)	C25—H45	0.931
P2—O1—C6	119 (2)	C11—C12—H34	119.9
O1—P2—C3	103.7 (15)	C13—C12—H34	121.4
O1—P2—O7	117.5 (14)	C8—C13—C12	127 (4)
C3—P2—O7	114.1 (14)	C8—C13—H35	116.6
O1—P2—C20	104.2 (15)	C12—C13—H35	116.7
C3—P2—C20	104.1 (17)	C3—C14—C15	118 (4)
O7—P2—C20	111.9 (14)	C3—C14—C19	119 (3)
P2—C3—N4	102 (2)	C15—C14—C19	123 (3)
P2—C3—C14	115 (3)	C14—C15—C16	116 (3)
N4—C3—C14	112 (3)	C14—C15—H36	122.6
P2—C3—H30	108.4	C16—C15—H36	121.8
N4—C3—H30	109.7	C15—C16—C17	115 (3)
C14—C3—H30	109.3	C15—C16—H37	123.0
C3—N4—C5	110 (3)	C17—C16—H37	122.3
C3—N4—H29	121.9	C16—C17—C18	125 (4)
C5—N4—H29	127.6	C16—C17—H38	117.7
N4—C5—C6	119 (3)	C18—C17—H38	117.1
N4—C5—C8	112 (3)	C17—C18—C19	119 (4)
C6—C5—C8	104 (3)	C17—C18—H39	119.9
N4—C5—H28	108.3	C19—C18—H39	120.9
C6—C5—H28	106.2	C14—C19—C18	122 (4)
C8—C5—H28	106.7	C14—C19—H40	119.4
C5—C6—O1	106 (3)	C18—C19—H40	118.9
C5—C6—H26	110.2	P2—C20—C21	127 (3)
O1—C6—H26	111.0	P2—C20—C25	118 (2)
C5—C6—H27	110.6	C21—C20—C25	115 (3)
O1—C6—H27	109.3	C20—C21—C22	123 (3)
H26—C6—H27	109.5	C20—C21—H41	118.6
C5—C8—C9	121 (3)	C22—C21—H41	118.5
C5—C8—C13	121 (4)	C21—C22—C23	119 (3)
C9—C8—C13	116 (3)	C21—C22—H42	120.6
C8—C9—C10	119 (4)	C23—C22—H42	120.0
C8—C9—H31	120.1	C22—C23—C24	118 (3)
C10—C9—H31	120.9	C22—C23—H43	120.9
C9—C10—C11	126 (4)	C24—C23—H43	121.1
C9—C10—H32	117.0	C23—C24—C25	120 (3)
C11—C10—H32	117.0	C23—C24—H44	120.1
C10—C11—C12	113 (3)	C25—C24—H44	119.9
C10—C11—H33	123.8	C20—C25—C24	123 (3)
C12—C11—H33	123.7	C20—C25—H45	118.4
C11—C12—C13	119 (4)	C24—C25—H45	118.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H30···O7^i	0.98	2.25	3.23 (5)	177

Symmetry code: (i) x−1, y, z.

(IX) (2R,3S,5S)-3,5-diphenyl-[1,4,2]-oxazaphosphorinane 2-oxide.

Crystal data

C15H16NO2P	F(000) = 576
Mr = 273.27	Dx = 1.326 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2867 reflections
a = 5.3914 (2) Å	θ = 2.8–32.4°
b = 11.7559 (4) Å	µ = 0.20 mm^−1
c = 21.6032 (8) Å	T = 175 K
V = 1369.23 (9) Å^3	Prism, translucent pale white
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	4506 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1197 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.4205 pixels mm^-1	θmax = 32.5°, θmin = 3.3°
ω scans	h = −8→7
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −17→16
Tmin = 0.940, Tmax = 0.961	l = −31→29
26882 measured reflections

Refinement

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.028	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 Ai are: 27.8 -41.7 34.0 -14.2 6.83
wR(F^2) = 0.029	(Δ/σ)max = 0.014
S = 1.11	Δρmax = 0.12 e Å^−3
1197 reflections	Δρmin = −0.18 e Å^−3
173 parameters	Absolute structure: Flack (1983), 1866 Friedel-pairs
0 restraints	Absolute structure parameter: −0.10 (16)
Primary atom site location: structure-invariant direct methods

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

	x	y	z	Uiso*/Ueq
O1	0.2584 (5)	0.02455 (16)	0.84333 (9)	0.0464
P2	0.2897 (2)	0.03856 (7)	0.77056 (4)	0.0449
C3	0.4148 (6)	0.1804 (3)	0.76198 (14)	0.0349
N4	0.2608 (5)	0.25689 (19)	0.79954 (10)	0.0345
C5	0.2697 (6)	0.2298 (2)	0.86558 (12)	0.0365
C6	0.1378 (7)	0.1162 (3)	0.87593 (15)	0.0407
O7	0.4345 (5)	−0.0532 (2)	0.74238 (10)	0.0629
C8	0.4170 (6)	0.2124 (3)	0.69417 (15)	0.0359
C9	0.2314 (7)	0.2759 (3)	0.66782 (14)	0.0398
C10	0.2332 (9)	0.3003 (3)	0.60526 (16)	0.0509
C11	0.4257 (8)	0.2620 (3)	0.56872 (18)	0.0545
C12	0.6093 (8)	0.1980 (3)	0.59410 (16)	0.0523
C13	0.6079 (7)	0.1737 (3)	0.65689 (15)	0.0449
C14	0.1392 (6)	0.3206 (3)	0.90303 (14)	0.0356
C15	0.2224 (7)	0.3493 (3)	0.96196 (14)	0.0420
C16	0.1000 (8)	0.4300 (3)	0.99651 (16)	0.0475
C17	−0.1063 (8)	0.4844 (3)	0.97243 (17)	0.0492
C18	−0.1890 (7)	0.4578 (3)	0.91430 (15)	0.0478
C19	−0.0676 (7)	0.3747 (3)	0.87953 (17)	0.0438
H20	0.0473	0.0429	0.7467	0.0419*
H21	0.5848	0.1806	0.7782	0.0422*
H23	0.4426	0.2261	0.8796	0.0431*
H24	−0.0347	0.1249	0.8597	0.0495*
H25	0.1373	0.0984	0.9201	0.0494*
H26	0.7332	0.1302	0.6735	0.0540*
H27	0.7402	0.1705	0.5699	0.0619*
H28	0.4264	0.2796	0.5264	0.0658*
H29	0.1064	0.3417	0.5882	0.0599*
H30	0.1030	0.3037	0.6923	0.0474*
H31	0.3651	0.3141	0.9767	0.0504*
H32	0.1562	0.4491	1.0366	0.0558*
H33	−0.1923	0.5398	0.9952	0.0582*
H34	−0.3263	0.4947	0.8975	0.0578*
H35	−0.1254	0.3559	0.8399	0.0519*
H22	0.3276	0.3406	0.7951	0.0500*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0721 (18)	0.0329 (11)	0.0340 (11)	0.0117 (14)	0.0004 (14)	0.0039 (10)
P2	0.0662 (7)	0.0338 (4)	0.0345 (4)	0.0085 (5)	−0.0050 (5)	0.0013 (4)
C3	0.0274 (18)	0.0393 (17)	0.0380 (19)	−0.0005 (15)	−0.0024 (16)	−0.0008 (16)
N4	0.0400 (15)	0.0321 (12)	0.0315 (13)	0.0005 (15)	0.0057 (14)	−0.0017 (10)
C5	0.036 (2)	0.0417 (17)	0.0321 (16)	0.0018 (19)	−0.0031 (18)	0.0012 (14)
C6	0.054 (3)	0.0385 (17)	0.0293 (16)	0.0063 (17)	0.0032 (17)	0.0054 (15)
O7	0.099 (2)	0.0465 (14)	0.0426 (15)	0.0252 (16)	−0.0013 (14)	−0.0032 (12)
C8	0.038 (2)	0.0387 (18)	0.0305 (16)	−0.0066 (17)	−0.0003 (17)	−0.0006 (15)
C9	0.039 (2)	0.0448 (17)	0.0360 (17)	−0.005 (2)	−0.0028 (19)	−0.0015 (14)
C10	0.057 (3)	0.052 (2)	0.044 (2)	−0.002 (2)	−0.012 (2)	0.0083 (17)
C11	0.067 (3)	0.061 (2)	0.036 (2)	−0.027 (2)	−0.006 (2)	0.0077 (19)
C12	0.057 (3)	0.061 (2)	0.039 (2)	−0.013 (2)	0.0104 (19)	−0.0034 (19)
C13	0.036 (2)	0.056 (2)	0.043 (2)	−0.0057 (19)	0.0013 (16)	−0.0003 (18)
C14	0.038 (2)	0.0355 (16)	0.0332 (17)	−0.0004 (17)	0.0067 (16)	0.0051 (15)
C15	0.043 (2)	0.0442 (17)	0.0388 (19)	−0.0005 (19)	0.0019 (19)	−0.0012 (15)
C16	0.064 (3)	0.043 (2)	0.0360 (19)	−0.007 (2)	0.0056 (18)	−0.0067 (15)
C17	0.062 (3)	0.036 (2)	0.049 (2)	0.0012 (18)	0.018 (2)	−0.0025 (16)
C18	0.050 (2)	0.0447 (18)	0.048 (2)	0.016 (2)	0.0068 (18)	0.0082 (18)
C19	0.048 (2)	0.044 (2)	0.0400 (19)	0.0024 (19)	0.0047 (19)	−0.0006 (16)

Geometric parameters (Å, º)

O1—P2	1.590 (2)	C10—C11	1.379 (5)
O1—C6	1.442 (4)	C10—H29	0.916
P2—C3	1.808 (3)	C11—C12	1.359 (5)
P2—O7	1.464 (2)	C11—H28	0.937
P2—H20	1.406	C12—C13	1.386 (5)
C3—N4	1.469 (4)	C12—H27	0.936
C3—C8	1.513 (4)	C13—H26	0.921
C3—H21	0.981	C14—C15	1.391 (4)
N4—C5	1.463 (4)	C14—C19	1.380 (5)
N4—H22	1.052	C15—C16	1.375 (4)
C5—C6	1.529 (4)	C15—H31	0.930
C5—C14	1.513 (4)	C16—C17	1.385 (5)
C5—H23	0.981	C16—H32	0.944
C6—H24	0.999	C17—C18	1.369 (5)
C6—H25	0.978	C17—H33	0.939
C8—C9	1.372 (5)	C18—C19	1.396 (5)
C8—C13	1.384 (5)	C18—H34	0.931
C9—C10	1.382 (5)	C19—H35	0.938
C9—H30	0.930
P2—O1—C6	116.95 (18)	C8—C9—H30	119.9
O1—P2—C3	103.67 (13)	C10—C9—H30	119.2
O1—P2—O7	113.04 (13)	C9—C10—C11	119.8 (4)
C3—P2—O7	115.96 (16)	C9—C10—H29	119.8
O1—P2—H20	105.6	C11—C10—H29	120.3
C3—P2—H20	106.0	C10—C11—C12	119.8 (4)
O7—P2—H20	111.7	C10—C11—H28	119.3
P2—C3—N4	107.3 (2)	C12—C11—H28	120.8
P2—C3—C8	109.4 (2)	C11—C12—C13	120.3 (4)
N4—C3—C8	112.8 (3)	C11—C12—H27	121.0
P2—C3—H21	108.4	C13—C12—H27	118.7
N4—C3—H21	109.2	C12—C13—C8	120.4 (4)
C8—C3—H21	109.7	C12—C13—H26	119.5
C3—N4—C5	112.8 (2)	C8—C13—H26	120.1
C3—N4—H22	109.2	C5—C14—C15	120.7 (3)
C5—N4—H22	106.3	C5—C14—C19	120.3 (3)
N4—C5—C6	108.5 (2)	C15—C14—C19	119.0 (3)
N4—C5—C14	110.6 (2)	C14—C15—C16	120.6 (4)
C6—C5—C14	108.8 (3)	C14—C15—H31	118.2
N4—C5—H23	110.0	C16—C15—H31	121.2
C6—C5—H23	111.0	C15—C16—C17	120.0 (3)
C14—C5—H23	107.9	C15—C16—H32	120.5
C5—C6—O1	111.8 (3)	C17—C16—H32	119.5
C5—C6—H24	107.0	C16—C17—C18	120.1 (3)
O1—C6—H24	109.0	C16—C17—H33	121.4
C5—C6—H25	109.4	C18—C17—H33	118.6
O1—C6—H25	108.5	C17—C18—C19	120.1 (3)
H24—C6—H25	111.2	C17—C18—H34	120.6
C3—C8—C9	122.1 (3)	C19—C18—H34	119.3
C3—C8—C13	119.2 (3)	C18—C19—C14	120.2 (3)
C9—C8—C13	118.7 (3)	C18—C19—H35	120.0
C8—C9—C10	120.9 (4)	C14—C19—H35	119.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H22···O7^i	1.05	1.96	2.916 (2)	149

Symmetry code: (i) −x+1, y+1/2, −z+3/2.