Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053190/hk2174sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053190/hk2174Isup2.hkl |
CCDC reference: 633889
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).
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) Å3 | Cuboid, colorless |
Z = 4 | 0.36 × 0.3 × 0.2 mm |
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 on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.011P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.03 | (Δ/σ)max = 0.001 |
wR(F2) = 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 |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |