Butyl­diphenyl­phosphine oxide

The solid state structure of the title compound, C₁₆H₁₉OP, an organic tertiary phosphine oxide, is stabilized mainly by C—H...π inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.084
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group Pc      ....    Pn
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           28.00
           From the CIF: _reflns_number_total               2532
           Count of symmetry unique reflns         1707
           Completeness (_total/calc)            148.33%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       825
           Fraction of Friedel pairs measured     0.483
           Are heavy atom types Z>Si present        yes

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

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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Butyldiphenylphosphine oxide

Crystal data

C16H19OP	F(000) = 276
Mr = 258.28	Dx = 1.210 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 4597 reflections
a = 8.1289 (12) Å	θ = 2.8–28.0°
b = 5.9814 (9) Å	µ = 0.18 mm^−1
c = 14.600 (2) Å	T = 173 K
β = 93.326 (3)°	Block, colourless
V = 708.68 (18) Å^3	0.44 × 0.32 × 0.22 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2474 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 28.0°, θmin = 2.8°
φ and ω scans	h = −10→10
4597 measured reflections	k = −7→7
2532 independent reflections	l = −13→19

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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.118P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.011
2532 reflections	Δρmax = 0.34 e Å^−3
163 parameters	Δρmin = −0.19 e Å^−3
2 restraints	Absolute structure: Flack (1983), 825 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (8)

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
C1	1.1563 (4)	1.0649 (5)	0.5347 (3)	0.0627 (9)
H1A	1.2643	1.1300	0.5518	0.094*
H1B	1.0777	1.1077	0.5800	0.094*
H1C	1.1174	1.1204	0.4741	0.094*
C2	1.1705 (3)	0.8160 (4)	0.5318 (2)	0.0496 (6)
H2A	1.2143	0.7628	0.5927	0.060*
H2B	1.2515	0.7753	0.4865	0.060*
C3	1.0083 (2)	0.6934 (4)	0.50681 (17)	0.0369 (5)
H3A	0.9628	0.7470	0.4464	0.044*
H3B	1.0304	0.5313	0.5015	0.044*
C4	0.8808 (2)	0.7304 (3)	0.57832 (14)	0.0269 (4)
H4A	0.8451	0.8886	0.5757	0.032*
H4B	0.9340	0.7033	0.6401	0.032*
C5	0.5977 (2)	0.8485 (3)	0.41890 (14)	0.0282 (4)
H5	0.6628	0.9617	0.4488	0.034*
C6	0.5103 (3)	0.8943 (3)	0.33628 (17)	0.0354 (5)
H6	0.5189	1.0376	0.3089	0.043*
C7	0.4103 (3)	0.7314 (4)	0.29335 (16)	0.0391 (5)
H7	0.3512	0.7633	0.2368	0.047*
C8	0.3976 (3)	0.5221 (4)	0.33369 (17)	0.0382 (5)
H8	0.3268	0.4123	0.3057	0.046*
C9	0.4879 (2)	0.4734 (3)	0.41442 (15)	0.0301 (4)
H9	0.4808	0.3286	0.4406	0.036*
C10	0.58943 (19)	0.6347 (3)	0.45798 (12)	0.0218 (3)
C11	0.5709 (2)	0.8430 (3)	0.69449 (16)	0.0321 (4)
H11	0.6354	0.9591	0.6703	0.039*
C12	0.4757 (3)	0.8855 (4)	0.76880 (18)	0.0412 (5)
H12	0.4785	1.0292	0.7966	0.049*
C13	0.3769 (3)	0.7198 (4)	0.80247 (17)	0.0411 (5)
H13	0.3125	0.7498	0.8533	0.049*
C14	0.3719 (3)	0.5099 (4)	0.76207 (18)	0.0390 (5)
H14	0.3016	0.3973	0.7839	0.047*
C15	0.4703 (2)	0.4650 (3)	0.68941 (16)	0.0314 (4)
H15	0.4684	0.3202	0.6626	0.038*
C16	0.57178 (19)	0.6297 (3)	0.65537 (13)	0.0226 (3)
P	0.70109 (4)	0.55356 (6)	0.56337 (3)	0.02075 (11)
O	0.73584 (14)	0.3074 (2)	0.56441 (11)	0.0288 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0521 (15)	0.0615 (17)	0.076 (2)	−0.0264 (12)	0.0124 (14)	−0.0143 (15)
C2	0.0267 (10)	0.0600 (15)	0.0630 (17)	−0.0001 (9)	0.0095 (10)	0.0076 (13)
C3	0.0330 (9)	0.0358 (10)	0.0428 (12)	−0.0013 (8)	0.0113 (9)	−0.0057 (10)
C4	0.0237 (7)	0.0285 (8)	0.0282 (9)	−0.0048 (6)	−0.0001 (7)	−0.0010 (7)
C5	0.0323 (8)	0.0229 (7)	0.0292 (10)	−0.0008 (7)	0.0001 (7)	0.0002 (7)
C6	0.0467 (12)	0.0267 (8)	0.0323 (11)	0.0071 (8)	−0.0023 (9)	0.0036 (9)
C7	0.0487 (12)	0.0389 (11)	0.0281 (11)	0.0126 (9)	−0.0112 (9)	−0.0042 (9)
C8	0.0449 (11)	0.0326 (10)	0.0354 (12)	−0.0004 (8)	−0.0115 (9)	−0.0091 (9)
C9	0.0350 (9)	0.0234 (8)	0.0315 (11)	−0.0019 (7)	−0.0019 (8)	−0.0025 (8)
C10	0.0242 (7)	0.0222 (7)	0.0187 (8)	0.0016 (6)	0.0000 (6)	−0.0007 (7)
C11	0.0388 (10)	0.0232 (8)	0.0350 (11)	−0.0020 (7)	0.0074 (8)	0.0001 (8)
C12	0.0557 (13)	0.0282 (9)	0.0410 (13)	0.0069 (9)	0.0147 (11)	−0.0026 (9)
C13	0.0480 (12)	0.0404 (11)	0.0368 (13)	0.0108 (9)	0.0179 (10)	0.0049 (10)
C14	0.0407 (11)	0.0364 (10)	0.0414 (13)	−0.0003 (8)	0.0140 (9)	0.0111 (10)
C15	0.0356 (10)	0.0252 (8)	0.0339 (11)	−0.0042 (7)	0.0059 (8)	0.0020 (8)
C16	0.0239 (7)	0.0240 (7)	0.0199 (8)	0.0007 (6)	0.0006 (6)	0.0013 (7)
P	0.02212 (18)	0.01903 (17)	0.0210 (2)	0.00044 (17)	0.00011 (14)	−0.00015 (18)
O	0.0334 (7)	0.0196 (5)	0.0334 (7)	0.0037 (4)	0.0008 (6)	−0.0003 (6)

Geometric parameters (Å, º)

C1—C2	1.494 (4)	C7—H7	0.95
C1—H1A	0.98	C8—C9	1.383 (3)
C1—H1B	0.98	C8—H8	0.95
C1—H1C	0.98	C9—C10	1.398 (3)
C2—C3	1.534 (3)	C9—H9	0.95
C2—H2A	0.99	C10—P	1.8071 (19)
C2—H2B	0.99	C11—C12	1.392 (3)
C3—C4	1.529 (3)	C11—C16	1.398 (3)
C3—H3A	0.99	C11—H11	0.95
C3—H3B	0.99	C12—C13	1.384 (3)
C4—P	1.8067 (17)	C12—H12	0.95
C4—H4A	0.99	C13—C14	1.387 (3)
C4—H4B	0.99	C13—H13	0.95
C5—C6	1.391 (3)	C14—C15	1.391 (3)
C5—C10	1.403 (2)	C14—H14	0.95
C5—H5	0.95	C15—C16	1.395 (2)
C6—C7	1.394 (3)	C15—H15	0.95
C6—H6	0.95	C16—P	1.8111 (17)
C7—C8	1.390 (3)	P—O	1.4991 (13)
C2—C1—H1A	109.5	C9—C8—C7	120.1 (2)
C2—C1—H1B	109.5	C9—C8—H8	119.9
H1A—C1—H1B	109.5	C7—C8—H8	119.9
C2—C1—H1C	109.5	C8—C9—C10	120.82 (19)
H1A—C1—H1C	109.5	C8—C9—H9	119.6
H1B—C1—H1C	109.5	C10—C9—H9	119.6
C1—C2—C3	114.6 (2)	C9—C10—C5	118.99 (18)
C1—C2—H2A	108.6	C9—C10—P	117.12 (14)
C3—C2—H2A	108.6	C5—C10—P	123.89 (14)
C1—C2—H2B	108.6	C12—C11—C16	120.06 (18)
C3—C2—H2B	108.6	C12—C11—H11	120.0
H2A—C2—H2B	107.6	C16—C11—H11	120.0
C4—C3—C2	112.05 (19)	C13—C12—C11	120.4 (2)
C4—C3—H3A	109.2	C13—C12—H12	119.8
C2—C3—H3A	109.2	C11—C12—H12	119.8
C4—C3—H3B	109.2	C12—C13—C14	120.1 (2)
C2—C3—H3B	109.2	C12—C13—H13	120.0
H3A—C3—H3B	107.9	C14—C13—H13	120.0
C3—C4—P	114.08 (14)	C13—C14—C15	119.67 (19)
C3—C4—H4A	108.7	C13—C14—H14	120.2
P—C4—H4A	108.7	C15—C14—H14	120.2
C3—C4—H4B	108.7	C14—C15—C16	120.90 (19)
P—C4—H4B	108.7	C14—C15—H15	119.6
H4A—C4—H4B	107.6	C16—C15—H15	119.6
C6—C5—C10	119.86 (18)	C15—C16—C11	118.81 (17)
C6—C5—H5	120.1	C15—C16—P	117.87 (14)
C10—C5—H5	120.1	C11—C16—P	123.31 (13)
C5—C6—C7	120.48 (19)	O—P—C4	115.03 (8)
C5—C6—H6	119.8	O—P—C16	110.89 (8)
C7—C6—H6	119.8	C4—P—C16	105.27 (9)
C8—C7—C6	119.6 (2)	O—P—C10	110.95 (8)
C8—C7—H7	120.2	C4—P—C10	107.95 (9)
C6—C7—H7	120.2	C16—P—C10	106.23 (8)
C1—C2—C3—C4	−63.5 (3)	C12—C11—C16—P	−176.06 (18)
C2—C3—C4—P	−169.96 (16)	C3—C4—P—O	57.65 (18)
C10—C5—C6—C7	2.1 (3)	C3—C4—P—C16	−179.98 (15)
C5—C6—C7—C8	0.2 (3)	C3—C4—P—C10	−66.83 (16)
C6—C7—C8—C9	−2.1 (3)	C15—C16—P—O	−24.95 (18)
C7—C8—C9—C10	1.8 (3)	C11—C16—P—O	154.01 (16)
C8—C9—C10—C5	0.5 (3)	C15—C16—P—C4	−149.95 (16)
C8—C9—C10—P	179.71 (16)	C11—C16—P—C4	29.01 (19)
C6—C5—C10—C9	−2.4 (3)	C15—C16—P—C10	95.70 (16)
C6—C5—C10—P	178.44 (15)	C11—C16—P—C10	−85.34 (18)
C16—C11—C12—C13	−2.3 (4)	C9—C10—P—O	28.55 (16)
C11—C12—C13—C14	−0.2 (4)	C5—C10—P—O	−152.27 (14)
C12—C13—C14—C15	1.9 (4)	C9—C10—P—C4	155.44 (14)
C13—C14—C15—C16	−1.3 (4)	C5—C10—P—C4	−25.37 (17)
C14—C15—C16—C11	−1.1 (3)	C9—C10—P—C16	−92.05 (15)
C14—C15—C16—P	177.86 (18)	C5—C10—P—C16	87.13 (16)
C12—C11—C16—C15	2.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2^i	0.99	2.86	3.676 (3)	153
C2—H2B···Cg1^i	0.99	2.71	3.695 (3)	174
C14—H14···Cg1^ii	0.95	2.91	3.729 (3)	145

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