tert-Butyl di­phenyl­phosphinate

Mol­ecules of the title compound, C₁₆H₁₉O₂P, pack simply in the orthorhombic space group Pbca, the dominant molecular feature being a tetrahedral P atom attached to two phenyl rings, a phosphate O atom and a tertiary butyloxy group.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.039
• wR factor = 0.142
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level A
TYPE059_ALERT_1_A  _diffrn_reflns_av_R_equivalents is not of type numb.

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         30 Perc.

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    P1     -   O1      ..       5.37 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for        C25
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C21
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C41
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C21    -C26           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SDP (Frenz, 1985); cell refinement: SDP; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

tert-Butyl diphenylphosphinate

Crystal data

C16H19O2P	F(000) = 1168
Mr = 274.28	Dx = 1.208 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 11.530 (2) Å	θ = 10.0–12.0°
b = 17.118 (2) Å	µ = 0.18 mm^−1
c = 15.285 (2) Å	T = 293 K
V = 3016.8 (7) Å^3	Needle, colourless
Z = 8	0.40 × 0.13 × 0.12 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	802 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.4°
Graphite monochromator	h = 0→13
w–2θ scans	k = 0→20
Absorption correction: ψ scan (North et al., 1968)	l = 0→18
Tmin = 0.954, Tmax = 0.979	25 standard reflections every 120 min
2631 measured reflections	intensity decay: 1%
2631 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0552P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
2631 reflections	Δρmax = 0.20 e Å^−3
173 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
P1	0.25644 (13)	0.32403 (7)	0.03879 (8)	0.0521 (4)
O1	0.1377 (3)	0.35046 (18)	0.05965 (19)	0.0689 (10)
C11	0.2716 (4)	0.2197 (2)	0.0466 (3)	0.0457 (11)
C12	0.3702 (4)	0.1814 (3)	0.0175 (3)	0.0579 (13)
H12	0.4304	0.2098	−0.0076	0.069*
C13	0.3797 (5)	0.1018 (3)	0.0254 (4)	0.0711 (16)
H13	0.4467	0.0768	0.0062	0.085*
C14	0.2915 (6)	0.0587 (3)	0.0612 (3)	0.0729 (17)
H14	0.2985	0.0048	0.0667	0.087*
C15	0.1925 (5)	0.0960 (4)	0.0890 (3)	0.0699 (16)
H15	0.1321	0.0671	0.1130	0.084*
C16	0.1820 (4)	0.1755 (3)	0.0818 (3)	0.0572 (13)
H16	0.1144	0.2001	0.1005	0.069*
C21	0.3645 (5)	0.3639 (3)	0.1104 (3)	0.0496 (12)
C22	0.3411 (5)	0.3652 (3)	0.1986 (3)	0.0780 (16)
H22	0.2702	0.3465	0.2188	0.094*
C23	0.4217 (7)	0.3938 (3)	0.2577 (4)	0.095 (2)
H23	0.4052	0.3939	0.3173	0.114*
C24	0.5244 (6)	0.4218 (4)	0.2285 (5)	0.096 (2)
H24	0.5787	0.4411	0.2681	0.115*
C25	0.5483 (5)	0.4217 (4)	0.1422 (5)	0.104 (2)
H25	0.6192	0.4406	0.1223	0.125*
C26	0.4675 (5)	0.3937 (3)	0.0830 (4)	0.0784 (17)
H26	0.4841	0.3952	0.0235	0.094*
O4	0.3092 (2)	0.34817 (16)	−0.05186 (18)	0.0587 (8)
C41	0.2548 (5)	0.3447 (3)	−0.1397 (3)	0.0604 (13)
C42	0.3584 (5)	0.3418 (3)	−0.2007 (3)	0.0839 (17)
H42A	0.4181	0.3759	−0.1792	0.126*
H42B	0.3352	0.3584	−0.2581	0.126*
H42C	0.3875	0.2894	−0.2035	0.126*
C43	0.1783 (5)	0.2742 (3)	−0.1490 (3)	0.0806 (17)
H43A	0.2231	0.2278	−0.1383	0.121*
H43B	0.1470	0.2724	−0.2071	0.121*
H43C	0.1161	0.2772	−0.1073	0.121*
C44	0.1867 (5)	0.4199 (3)	−0.1512 (3)	0.0865 (17)
H44A	0.1282	0.4233	−0.1067	0.130*
H44B	0.1506	0.4201	−0.2078	0.130*
H44C	0.2383	0.4637	−0.1465	0.130*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0522 (8)	0.0523 (7)	0.0519 (7)	0.0012 (8)	−0.0034 (9)	−0.0001 (7)
O1	0.0463 (19)	0.081 (2)	0.080 (2)	0.0158 (18)	−0.002 (2)	−0.0103 (19)
C11	0.043 (3)	0.052 (3)	0.042 (2)	−0.007 (3)	0.002 (3)	−0.001 (2)
C12	0.062 (4)	0.051 (4)	0.060 (3)	−0.005 (3)	0.008 (3)	0.002 (3)
C13	0.066 (4)	0.059 (4)	0.087 (5)	0.011 (3)	−0.011 (3)	−0.006 (3)
C14	0.093 (5)	0.052 (3)	0.074 (4)	−0.012 (4)	−0.027 (3)	0.002 (3)
C15	0.071 (4)	0.067 (4)	0.072 (4)	−0.024 (4)	−0.011 (4)	0.014 (3)
C16	0.048 (3)	0.069 (4)	0.055 (3)	−0.004 (3)	−0.003 (2)	0.005 (3)
C21	0.058 (3)	0.047 (3)	0.044 (3)	0.006 (3)	−0.006 (3)	−0.003 (2)
C22	0.092 (5)	0.078 (4)	0.064 (4)	−0.011 (4)	−0.005 (4)	−0.004 (3)
C23	0.133 (7)	0.083 (5)	0.068 (4)	−0.005 (4)	−0.015 (5)	−0.001 (4)
C24	0.099 (7)	0.090 (5)	0.100 (6)	0.015 (5)	−0.047 (5)	−0.035 (5)
C25	0.063 (4)	0.132 (5)	0.118 (6)	−0.016 (4)	−0.018 (4)	−0.037 (5)
C26	0.061 (4)	0.098 (4)	0.076 (4)	−0.012 (3)	0.002 (4)	−0.022 (3)
O4	0.0665 (19)	0.065 (2)	0.0451 (19)	−0.0121 (16)	−0.0100 (18)	0.0048 (16)
C41	0.071 (3)	0.064 (3)	0.046 (3)	0.002 (4)	−0.005 (3)	0.001 (2)
C42	0.083 (4)	0.110 (5)	0.058 (3)	−0.007 (4)	0.001 (3)	−0.002 (3)
C43	0.089 (4)	0.083 (4)	0.070 (3)	−0.020 (4)	−0.021 (3)	−0.005 (3)
C44	0.097 (4)	0.082 (4)	0.081 (4)	0.012 (4)	−0.009 (4)	0.012 (3)

Geometric parameters (Å, º)

P1—O1	1.476 (3)	C23—H23	0.9300
P1—O4	1.569 (3)	C24—C25	1.348 (8)
P1—C21	1.793 (5)	C24—H24	0.9300
P1—C11	1.798 (4)	C25—C26	1.384 (6)
C11—C12	1.387 (6)	C25—H25	0.9300
C11—C16	1.389 (5)	C26—H26	0.9300
C12—C13	1.373 (6)	C41—O4	1.483 (5)
C12—H12	0.9300	C41—C43	1.502 (6)
C13—C14	1.371 (6)	C41—C42	1.516 (6)
C13—H13	0.9300	C41—C44	1.517 (6)
C14—C15	1.375 (6)	C42—H42A	0.9600
C14—H14	0.9300	C42—H42B	0.9600
C15—C16	1.371 (6)	C42—H42C	0.9600
C15—H15	0.9300	C43—H43A	0.9600
C16—H16	0.9300	C43—H43B	0.9600
C21—C26	1.358 (6)	C43—H43C	0.9600
C21—C22	1.375 (6)	C44—H44A	0.9600
C22—C23	1.386 (7)	C44—H44B	0.9600
C22—H22	0.9300	C44—H44C	0.9600
C23—C24	1.354 (8)
O1—P1—O4	118.00 (18)	C23—C24—H24	120.0
O1—P1—C21	113.3 (2)	C25—C24—H24	120.0
O4—P1—C21	99.7 (2)	C24—C25—C26	120.2 (6)
O1—P1—C11	112.3 (2)	C24—C25—H25	119.9
O4—P1—C11	106.40 (19)	C26—C25—H25	119.9
C21—P1—C11	105.7 (2)	C21—C26—C25	121.1 (5)
C12—C11—C16	118.5 (4)	C21—C26—H26	119.4
C12—C11—P1	121.9 (4)	C25—C26—H26	119.4
C16—C11—P1	119.6 (4)	O4—C41—C43	111.4 (3)
C13—C12—C11	120.5 (5)	O4—C41—C42	103.0 (4)
C13—C12—H12	119.8	C43—C41—C42	112.2 (4)
C11—C12—H12	119.7	O4—C41—C44	106.9 (4)
C12—C13—C14	120.6 (5)	C43—C41—C44	111.5 (5)
C12—C13—H13	119.7	C42—C41—C44	111.3 (4)
C14—C13—H13	119.7	C41—C42—H42A	109.5
C13—C14—C15	119.3 (5)	C41—C42—H42B	109.5
C13—C14—H14	120.3	H42A—C42—H42B	109.5
C15—C14—H14	120.3	C41—C42—H42C	109.5
C16—C15—C14	120.6 (5)	H42A—C42—H42C	109.5
C16—C15—H15	119.7	H42B—C42—H42C	109.5
C14—C15—H15	119.7	C41—C43—H43A	109.5
C15—C16—C11	120.4 (5)	C41—C43—H43B	109.5
C15—C16—H16	119.8	H43A—C43—H43B	109.5
C11—C16—H16	119.8	C41—C43—H43C	109.5
C26—C21—C22	117.9 (5)	H43A—C43—H43C	109.5
C26—C21—P1	124.2 (4)	H43B—C43—H43C	109.5
C22—C21—P1	117.9 (5)	C41—O4—P1	128.7 (3)
C21—C22—C23	120.9 (6)	C41—C44—H44A	109.5
C21—C22—H22	119.6	C41—C44—H44B	109.5
C23—C22—H22	119.6	H44A—C44—H44B	109.5
C24—C23—C22	119.8 (7)	C41—C44—H44C	109.5
C24—C23—H23	120.1	H44A—C44—H44C	109.5
C22—C23—H23	120.1	H44B—C44—H44C	109.5
C23—C24—C25	120.0 (7)