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
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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) |
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