Benzyl­diphenyl­phosphine selenide

In the mol­ecule of the title compound, SePPh₂Bz (Bz = benzyl, CH₂C₆H₅) or C₁₉H₁₇PSe, the Se atom and the three aryl groups adopt a distorted tetrahedral arrangement about the P atom. The effective cone angle was calculated to be 167°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.063
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.27
           From the CIF: _reflns_number_total               3343
           Count of symmetry unique reflns         2127
           Completeness (_total/calc)            157.17%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1216
           Fraction of Friedel pairs measured     0.572
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus and XPREP (Bruker, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Benzyldiphenylphosphine selenide

Crystal data

C19H17PSe	F(000) = 720
Mr = 355.26	Dx = 1.424 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 910 reflections
a = 10.572 (2) Å	θ = 2.5–26.7°
b = 9.789 (2) Å	µ = 2.35 mm^−1
c = 16.009 (3) Å	T = 294 K
V = 1656.8 (6) Å^3	Cuboid, colorless
Z = 4	0.36 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD 1K diffractometer	3343 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Detector resolution: 512 pixels mm^-1	Rint = 0.025
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→14
Tmin = 0.465, Tmax = 0.624	k = −13→7
6219 measured reflections	l = −21→20

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.011P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.03	(Δ/σ)max = 0.001
wR(F^2) = 0.063	Δρmax = 0.42 e Å^−3
S = 1	Δρmin = −0.21 e Å^−3
3343 reflections	Absolute structure: Flack (1983), with 1216 Friedel pairs
190 parameters	Absolute structure parameter: 0.025 (9)
1 restraint

Special details

Experimental. The intensity data were collected on a Bruker SMART CCD 1 K diffractometer using an exposure time of 15 s/frame. A total of 753 frames were collected with a frame width of 0.3° covering up to θ = 28.27° with 100% completeness accomplished. The first 50 frames were recollected at the end of the data collection to check for decay; none was found.

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.

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

	x	y	z	Uiso*/Ueq
Se	0.14335 (2)	0.37079 (3)	0.72887 (3)	0.04379 (9)
P	0.27691 (6)	0.43788 (7)	0.81796 (4)	0.03132 (15)
C1	0.3736 (2)	0.2992 (3)	0.8615 (2)	0.0406 (7)
H1A	0.4179	0.2535	0.8164	0.049*
H1B	0.4364	0.3377	0.8988	0.049*
C11	0.2949 (2)	0.1956 (3)	0.90883 (19)	0.0356 (6)
C12	0.2484 (3)	0.0800 (3)	0.8692 (2)	0.0447 (7)
H12	0.2642	0.0663	0.8127	0.054*
C13	0.1780 (3)	−0.0156 (3)	0.9138 (2)	0.0506 (8)
H13	0.1475	−0.0932	0.887	0.061*
C14	0.1533 (3)	0.0038 (4)	0.9969 (2)	0.0561 (9)
H14	0.1065	−0.0606	1.0264	0.067*
C15	0.1975 (4)	0.1178 (4)	1.0366 (3)	0.0587 (10)
H15	0.1801	0.1315	1.0929	0.07*
C16	0.2681 (3)	0.2130 (4)	0.9928 (2)	0.0496 (8)
H16	0.2981	0.2901	1.0203	0.059*
C21	0.3887 (2)	0.5581 (3)	0.77311 (17)	0.0332 (6)
C22	0.4924 (2)	0.5121 (3)	0.7279 (3)	0.0429 (6)
H22	0.5077	0.4189	0.7231	0.051*
C23	0.5725 (3)	0.6037 (4)	0.6902 (2)	0.0548 (8)
H23	0.6424	0.5718	0.6608	0.066*
C24	0.5507 (3)	0.7420 (4)	0.6954 (2)	0.0542 (8)
H24	0.6053	0.8035	0.6696	0.065*
C25	0.4478 (3)	0.7880 (3)	0.7387 (3)	0.0562 (9)
H25	0.4323	0.8813	0.7422	0.067*
C26	0.3669 (3)	0.6976 (3)	0.7773 (2)	0.0475 (8)
H26	0.2971	0.7304	0.8064	0.057*
C31	0.2101 (2)	0.5222 (3)	0.90894 (18)	0.0348 (6)
C32	0.2891 (3)	0.5870 (4)	0.9654 (2)	0.0480 (8)
H32	0.3751	0.5941	0.9539	0.058*
C33	0.2416 (4)	0.6414 (4)	1.0390 (2)	0.0598 (10)
H33	0.295	0.6849	1.0767	0.072*
C34	0.1133 (4)	0.6300 (4)	1.0556 (3)	0.0705 (12)
H34	0.0805	0.6657	1.1049	0.085*
C35	0.0350 (4)	0.5668 (4)	0.9999 (3)	0.0725 (12)
H35	−0.0509	0.5596	1.0114	0.087*
C36	0.0832 (3)	0.5131 (4)	0.9262 (2)	0.0522 (8)
H36	0.0292	0.4708	0.8883	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se	0.04800 (14)	0.04424 (16)	0.03914 (13)	−0.00718 (12)	−0.00641 (16)	−0.0039 (2)
P	0.0304 (3)	0.0323 (4)	0.0312 (3)	−0.0003 (3)	0.0023 (3)	−0.0016 (3)
C1	0.0341 (14)	0.0418 (18)	0.0460 (17)	0.0066 (11)	0.0027 (13)	0.0056 (15)
C11	0.0346 (14)	0.0374 (17)	0.0349 (15)	0.0054 (12)	−0.0041 (12)	0.0057 (15)
C12	0.0487 (16)	0.0384 (16)	0.0471 (17)	0.0069 (14)	−0.0019 (14)	−0.0004 (16)
C13	0.0503 (16)	0.0378 (18)	0.064 (2)	−0.0020 (13)	−0.0077 (16)	0.0023 (18)
C14	0.0465 (17)	0.057 (2)	0.064 (2)	−0.0030 (16)	0.0039 (17)	0.022 (2)
C15	0.066 (2)	0.068 (3)	0.0416 (19)	−0.0060 (18)	0.0072 (17)	0.007 (2)
C16	0.0593 (18)	0.050 (2)	0.0394 (16)	−0.0054 (16)	−0.0023 (15)	0.0033 (16)
C21	0.0320 (12)	0.0345 (16)	0.0330 (14)	−0.0019 (10)	−0.0004 (11)	−0.0008 (13)
C22	0.0461 (13)	0.0398 (14)	0.0427 (13)	0.0036 (11)	0.0058 (18)	0.004 (2)
C23	0.0441 (15)	0.067 (2)	0.0529 (18)	0.0029 (15)	0.0156 (15)	0.0063 (18)
C24	0.0554 (17)	0.055 (2)	0.0522 (18)	−0.0185 (15)	0.0092 (16)	0.0051 (17)
C25	0.0676 (17)	0.0354 (15)	0.066 (2)	−0.0081 (13)	0.011 (2)	−0.0052 (19)
C26	0.0468 (16)	0.0383 (17)	0.057 (2)	−0.0025 (13)	0.0157 (15)	−0.0050 (17)
C31	0.0355 (13)	0.0358 (16)	0.0329 (14)	0.0014 (11)	0.0023 (11)	−0.0018 (13)
C32	0.0462 (17)	0.056 (2)	0.0422 (17)	−0.0050 (15)	0.0034 (14)	−0.0103 (17)
C33	0.082 (3)	0.055 (2)	0.0430 (19)	−0.0051 (18)	0.0010 (18)	−0.0152 (18)
C34	0.091 (3)	0.068 (3)	0.052 (2)	−0.002 (2)	0.030 (2)	−0.016 (2)
C35	0.060 (2)	0.080 (3)	0.077 (3)	−0.0085 (19)	0.033 (2)	−0.024 (3)
C36	0.0422 (15)	0.058 (2)	0.056 (2)	−0.0078 (14)	0.0095 (15)	−0.0111 (18)

Geometric parameters (Å, º)

Se—P	2.1117 (8)	C22—C23	1.373 (4)
P—C21	1.815 (3)	C22—H22	0.93
P—C31	1.817 (3)	C23—C24	1.376 (5)
P—C1	1.836 (3)	C23—H23	0.93
C1—C11	1.514 (4)	C24—C25	1.366 (4)
C1—H1A	0.97	C24—H24	0.93
C1—H1B	0.97	C25—C26	1.377 (5)
C11—C16	1.384 (5)	C25—H25	0.93
C11—C12	1.388 (4)	C26—H26	0.93
C12—C13	1.393 (5)	C31—C36	1.372 (4)
C12—H12	0.93	C31—C32	1.385 (4)
C13—C14	1.369 (5)	C32—C33	1.386 (5)
C13—H13	0.93	C32—H32	0.93
C14—C15	1.366 (5)	C33—C34	1.386 (5)
C14—H14	0.93	C33—H33	0.93
C15—C16	1.384 (5)	C34—C35	1.365 (6)
C15—H15	0.93	C34—H34	0.93
C16—H16	0.93	C35—C36	1.389 (5)
C21—C26	1.387 (4)	C35—H35	0.93
C21—C22	1.389 (4)	C36—H36	0.93
C21—P—C31	106.00 (13)	C23—C22—C21	120.3 (3)
C21—P—C1	105.48 (12)	C23—C22—H22	119.8
C31—P—C1	104.35 (14)	C21—C22—H22	119.8
C21—P—Se	111.69 (9)	C22—C23—C24	120.9 (3)
C31—P—Se	115.00 (9)	C22—C23—H23	119.6
C1—P—Se	113.49 (11)	C24—C23—H23	119.6
C11—C1—P	112.31 (18)	C25—C24—C23	119.2 (3)
C11—C1—H1A	109.1	C25—C24—H24	120.4
P—C1—H1A	109.1	C23—C24—H24	120.4
C11—C1—H1B	109.1	C24—C25—C26	120.7 (3)
P—C1—H1B	109.1	C24—C25—H25	119.6
H1A—C1—H1B	107.9	C26—C25—H25	119.6
C16—C11—C12	118.1 (3)	C25—C26—C21	120.5 (3)
C16—C11—C1	121.1 (3)	C25—C26—H26	119.8
C12—C11—C1	120.8 (3)	C21—C26—H26	119.8
C11—C12—C13	120.2 (3)	C36—C31—C32	119.2 (3)
C11—C12—H12	119.9	C36—C31—P	120.8 (2)
C13—C12—H12	119.9	C32—C31—P	119.8 (2)
C14—C13—C12	120.5 (3)	C31—C32—C33	120.8 (3)
C14—C13—H13	119.8	C31—C32—H32	119.6
C12—C13—H13	119.8	C33—C32—H32	119.6
C15—C14—C13	120.0 (3)	C34—C33—C32	119.2 (4)
C15—C14—H14	120	C34—C33—H33	120.4
C13—C14—H14	120	C32—C33—H33	120.4
C14—C15—C16	119.9 (4)	C35—C34—C33	120.2 (3)
C14—C15—H15	120	C35—C34—H34	119.9
C16—C15—H15	120	C33—C34—H34	119.9
C11—C16—C15	121.3 (3)	C34—C35—C36	120.3 (3)
C11—C16—H16	119.3	C34—C35—H35	119.9
C15—C16—H16	119.3	C36—C35—H35	119.9
C26—C21—C22	118.4 (3)	C31—C36—C35	120.3 (3)
C26—C21—P	120.72 (19)	C31—C36—H36	119.8
C22—C21—P	120.7 (2)	C35—C36—H36	119.8
C21—P—C1—C11	174.7 (2)	C21—C22—C23—C24	−1.0 (6)
C31—P—C1—C11	63.2 (2)	C22—C23—C24—C25	0.0 (5)
Se—P—C1—C11	−62.7 (2)	C23—C24—C25—C26	0.4 (6)
P—C1—C11—C16	−87.7 (3)	C24—C25—C26—C21	0.2 (6)
P—C1—C11—C12	92.7 (3)	C22—C21—C26—C25	−1.2 (5)
C16—C11—C12—C13	−0.7 (4)	P—C21—C26—C25	−175.9 (3)
C1—C11—C12—C13	178.9 (3)	C21—P—C31—C36	138.3 (3)
C11—C12—C13—C14	0.4 (5)	C1—P—C31—C36	−110.6 (3)
C12—C13—C14—C15	0.2 (5)	Se—P—C31—C36	14.4 (3)
C13—C14—C15—C16	−0.6 (5)	C21—P—C31—C32	−47.1 (3)
C12—C11—C16—C15	0.3 (5)	C1—P—C31—C32	64.0 (3)
C1—C11—C16—C15	−179.3 (3)	Se—P—C31—C32	−171.0 (2)
C14—C15—C16—C11	0.3 (5)	C36—C31—C32—C33	0.5 (5)
C31—P—C21—C26	−33.2 (3)	P—C31—C32—C33	−174.2 (3)
C1—P—C21—C26	−143.5 (3)	C31—C32—C33—C34	0.1 (5)
Se—P—C21—C26	92.8 (2)	C32—C33—C34—C35	−0.4 (6)
C31—P—C21—C22	152.2 (3)	C33—C34—C35—C36	0.1 (7)
C1—P—C21—C22	41.9 (3)	C32—C31—C36—C35	−0.8 (5)
Se—P—C21—C22	−81.8 (3)	P—C31—C36—C35	173.8 (3)
C26—C21—C22—C23	1.5 (5)	C34—C35—C36—C31	0.5 (6)
P—C21—C22—C23	176.3 (3)