Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027710/dn6171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027710/dn6171Isup2.hkl |
CCDC reference: 259109
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.175
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C21H17OP | F(000) = 664.00 |
Mr = 316.34 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 9907 reflections |
a = 9.5560 (3) Å | θ = 1.3–27.3° |
b = 15.4559 (5) Å | µ = 0.17 mm−1 |
c = 12.0143 (3) Å | T = 296 K |
β = 108.904 (2)° | Block, colorless |
V = 1678.76 (9) Å3 | 0.57 × 0.25 × 0.15 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2484 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.038 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −12→12 |
Tmin = 0.820, Tmax = 0.975 | k = −18→20 |
15140 measured reflections | l = −14→15 |
3751 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[0.0059Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.175 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.30 e Å−3 |
2484 reflections | Δρmin = −0.34 e Å−3 |
208 parameters |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
P1 | 0.43434 (8) | 0.25859 (5) | 0.43802 (5) | 0.0362 (2) | |
O1 | 0.4443 (3) | 0.2791 (1) | 0.3202 (2) | 0.0516 (6) | |
C1 | 0.2871 (4) | 0.3994 (2) | 0.6313 (3) | 0.0546 (9) | |
C2 | 0.3866 (3) | 0.3736 (2) | 0.5875 (2) | 0.0410 (7) | |
C3 | 0.4868 (3) | 0.3472 (2) | 0.5414 (2) | 0.0366 (7) | |
C4 | 0.6348 (3) | 0.3893 (2) | 0.5700 (2) | 0.0400 (7) | |
C5 | 0.6692 (4) | 0.4597 (2) | 0.6452 (3) | 0.0549 (9) | |
C6 | 0.8071 (5) | 0.4987 (3) | 0.6730 (3) | 0.069 (1) | |
C7 | 0.9106 (4) | 0.4683 (3) | 0.6257 (3) | 0.066 (1) | |
C8 | 0.8784 (4) | 0.3989 (3) | 0.5513 (3) | 0.063 (1) | |
C9 | 0.7408 (4) | 0.3602 (2) | 0.5221 (3) | 0.0498 (9) | |
C10 | 0.5521 (3) | 0.1697 (2) | 0.5070 (2) | 0.0371 (7) | |
C11 | 0.5975 (3) | 0.1131 (2) | 0.4360 (3) | 0.0472 (8) | |
C12 | 0.6872 (4) | 0.0434 (2) | 0.4850 (3) | 0.058 (1) | |
C13 | 0.7329 (4) | 0.0301 (2) | 0.6038 (3) | 0.060 (1) | |
C14 | 0.6873 (4) | 0.0857 (2) | 0.6753 (3) | 0.061 (1) | |
C15 | 0.5979 (4) | 0.1555 (2) | 0.6280 (2) | 0.0474 (8) | |
C16 | 0.2479 (3) | 0.2300 (2) | 0.4293 (2) | 0.0406 (7) | |
C17 | 0.1368 (4) | 0.2502 (2) | 0.3253 (3) | 0.057 (1) | |
C18 | −0.0081 (4) | 0.2302 (3) | 0.3118 (4) | 0.075 (1) | |
C19 | −0.0424 (4) | 0.1892 (3) | 0.4005 (4) | 0.076 (1) | |
C20 | 0.0659 (4) | 0.1685 (3) | 0.5044 (4) | 0.069 (1) | |
C21 | 0.2108 (4) | 0.1891 (2) | 0.5188 (3) | 0.0530 (9) | |
H1 | 0.2184 | 0.4454 | 0.5917 | 0.066* | |
H2 | 0.2904 | 0.3754 | 0.7057 | 0.066* | |
H18 | −0.0858 | 0.2454 | 0.2397 | 0.085* | |
H6 | 0.8306 | 0.5478 | 0.7261 | 0.080* | |
H7 | 1.0066 | 0.4960 | 0.6449 | 0.077* | |
H14 | 0.7192 | 0.0759 | 0.7596 | 0.072* | |
H9 | 0.7180 | 0.3119 | 0.4675 | 0.060* | |
H8 | 0.9522 | 0.3767 | 0.5192 | 0.076* | |
H11 | 0.5663 | 0.1222 | 0.3516 | 0.058* | |
H12 | 0.7184 | 0.0040 | 0.4347 | 0.071* | |
H13 | 0.7966 | −0.0186 | 0.6377 | 0.071* | |
H15 | 0.5672 | 0.1945 | 0.6790 | 0.057* | |
H17 | 0.1611 | 0.2783 | 0.2618 | 0.065* | |
H5 | 0.5969 | 0.4818 | 0.6790 | 0.066* | |
H19 | −0.1446 | 0.1746 | 0.3900 | 0.092* | |
H20 | 0.0399 | 0.1395 | 0.5666 | 0.086* | |
H21 | 0.2870 | 0.1751 | 0.5924 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0359 (4) | 0.0406 (4) | 0.0320 (4) | −0.0009 (3) | 0.0110 (3) | −0.0006 (3) |
O1 | 0.056 (1) | 0.066 (1) | 0.034 (1) | −0.002 (1) | 0.0170 (9) | 0.0052 (9) |
C1 | 0.050 (2) | 0.059 (2) | 0.055 (2) | 0.007 (1) | 0.018 (2) | −0.008 (1) |
C2 | 0.043 (2) | 0.036 (1) | 0.041 (1) | 0.002 (1) | 0.009 (1) | −0.001 (1) |
C3 | 0.039 (2) | 0.035 (1) | 0.035 (1) | 0.001 (1) | 0.010 (1) | 0.003 (1) |
C4 | 0.040 (2) | 0.036 (1) | 0.039 (1) | −0.002 (1) | 0.007 (1) | 0.006 (1) |
C5 | 0.061 (2) | 0.050 (2) | 0.055 (2) | −0.012 (2) | 0.020 (2) | −0.006 (1) |
C6 | 0.076 (3) | 0.060 (2) | 0.065 (2) | −0.027 (2) | 0.013 (2) | −0.009 (2) |
C7 | 0.048 (2) | 0.073 (2) | 0.072 (2) | −0.021 (2) | 0.011 (2) | 0.008 (2) |
C8 | 0.046 (2) | 0.068 (2) | 0.076 (2) | −0.009 (2) | 0.019 (2) | 0.007 (2) |
C9 | 0.042 (2) | 0.049 (2) | 0.058 (2) | −0.005 (1) | 0.015 (1) | −0.001 (1) |
C10 | 0.033 (2) | 0.039 (1) | 0.041 (1) | −0.002 (1) | 0.013 (1) | −0.003 (1) |
C11 | 0.047 (2) | 0.050 (2) | 0.047 (2) | 0.002 (1) | 0.019 (1) | −0.007 (1) |
C12 | 0.061 (2) | 0.049 (2) | 0.069 (2) | 0.012 (2) | 0.028 (2) | −0.007 (1) |
C13 | 0.059 (2) | 0.047 (2) | 0.072 (2) | 0.013 (2) | 0.018 (2) | 0.006 (1) |
C14 | 0.075 (3) | 0.056 (2) | 0.049 (2) | 0.012 (2) | 0.015 (2) | 0.009 (1) |
C15 | 0.055 (2) | 0.048 (2) | 0.040 (1) | 0.006 (1) | 0.017 (1) | −0.001 (1) |
C16 | 0.039 (2) | 0.040 (1) | 0.042 (1) | −0.003 (1) | 0.012 (1) | −0.009 (1) |
C17 | 0.048 (2) | 0.066 (2) | 0.049 (2) | 0.000 (2) | 0.006 (1) | −0.010 (1) |
C18 | 0.041 (2) | 0.095 (3) | 0.075 (2) | 0.001 (2) | −0.000 (2) | −0.020 (2) |
C19 | 0.042 (2) | 0.085 (3) | 0.102 (3) | −0.017 (2) | 0.026 (2) | −0.036 (2) |
C20 | 0.058 (2) | 0.072 (2) | 0.086 (3) | −0.020 (2) | 0.036 (2) | −0.014 (2) |
C21 | 0.047 (2) | 0.058 (2) | 0.057 (2) | −0.007 (1) | 0.020 (1) | −0.004 (1) |
P1—O1 | 1.483 (2) | C17—C18 | 1.375 (6) |
P1—C3 | 1.808 (3) | C18—C19 | 1.368 (7) |
P1—C10 | 1.799 (3) | C19—C20 | 1.376 (5) |
P1—C16 | 1.805 (3) | C20—C21 | 1.376 (5) |
C1—C2 | 1.290 (5) | C1—H1 | 0.9805 |
C2—C3 | 1.316 (5) | C1—H2 | 0.9590 |
C3—C4 | 1.492 (4) | C5—H5 | 0.9700 |
C4—C5 | 1.385 (4) | C6—H6 | 0.9700 |
C4—C9 | 1.391 (5) | C7—H7 | 0.9700 |
C5—C6 | 1.388 (6) | C8—H8 | 0.9700 |
C6—C7 | 1.373 (7) | C9—H9 | 0.9700 |
C7—C8 | 1.366 (5) | C11—H11 | 0.9700 |
C8—C9 | 1.383 (5) | C12—H12 | 0.9700 |
C10—C11 | 1.386 (4) | C13—H13 | 0.9700 |
C10—C15 | 1.393 (4) | C14—H14 | 0.9700 |
C11—C12 | 1.384 (4) | C15—H15 | 0.9700 |
C12—C13 | 1.366 (5) | C17—H17 | 0.9700 |
C13—C14 | 1.382 (6) | C18—H18 | 0.9700 |
C14—C15 | 1.380 (5) | C19—H19 | 0.9700 |
C16—C17 | 1.388 (4) | C20—H20 | 0.9700 |
C16—C21 | 1.389 (5) | C21—H21 | 0.9700 |
C3—P1—O1 | 113.9 (1) | H1—C1—C2 | 119.5193 |
C10—P1—O1 | 112.3 (1) | H2—C1—C2 | 117.1031 |
C16—P1—O1 | 111.3 (1) | H2—C1—H1 | 123.1455 |
P1—C3—C2 | 116.5 (2) | C4—C5—H5 | 119.9554 |
P1—C3—C4 | 121.3 (2) | C4—C9—H9 | 119.5967 |
C10—P1—C3 | 105.6 (1) | H5—C5—C6 | 119.6936 |
C16—P1—C3 | 105.9 (1) | C5—C6—H6 | 119.8856 |
P1—C10—C11 | 118.2 (2) | H6—C6—C7 | 119.6977 |
P1—C10—C15 | 122.6 (2) | C6—C7—H7 | 120.2158 |
C16—P1—C10 | 107.3 (1) | C7—C8—H8 | 119.9838 |
P1—C16—C17 | 116.8 (3) | H7—C7—C8 | 119.8015 |
P1—C16—C21 | 124.1 (2) | C8—C9—H9 | 119.4185 |
C1—C2—C3 | 179.2 (3) | H8—C8—C9 | 120.0046 |
C2—C3—C4 | 122.2 (2) | C10—C11—H11 | 120.0109 |
C3—C4—C9 | 121.8 (2) | C10—C15—H15 | 120.2896 |
C3—C4—C5 | 120.0 (3) | H11—C11—C12 | 119.7037 |
C9—C4—C5 | 118.2 (3) | C11—C12—H12 | 119.7873 |
C4—C5—C6 | 120.4 (4) | H12—C12—C13 | 119.8370 |
C4—C9—C8 | 121.0 (3) | C12—C13—H13 | 120.0249 |
C5—C6—C7 | 120.4 (4) | C13—C14—H14 | 119.7412 |
C6—C7—C8 | 120.0 (4) | H13—C13—C14 | 120.1332 |
C7—C8—C9 | 120.0 (4) | C14—C15—H15 | 119.9015 |
C15—C10—C11 | 119.2 (3) | H14—C14—C15 | 119.7325 |
C10—C11—C12 | 120.3 (3) | C16—C17—H17 | 119.9915 |
C10—C15—C14 | 119.8 (3) | C16—C21—H21 | 120.1473 |
C11—C12—C13 | 120.4 (4) | H17—C17—C18 | 119.7607 |
C12—C13—C14 | 119.8 (3) | C17—C18—H18 | 120.0746 |
C13—C14—C15 | 120.5 (3) | H18—C18—C19 | 120.0540 |
C21—C16—C17 | 119.1 (3) | C18—C19—H19 | 119.4929 |
C16—C17—C18 | 120.2 (4) | C19—C20—H20 | 120.1052 |
C16—C21—C20 | 120.4 (3) | H19—C19—C20 | 119.5340 |
C17—C18—C19 | 119.9 (3) | C20—C21—H21 | 119.4185 |
C18—C19—C20 | 121.0 (4) | H20—C20—C21 | 120.5088 |
C19—C20—C21 | 119.4 (4) | ||
O(1)—P(1)—C(3)—C(2) | 122.1 (2) | C(9)—C(4)—C(5)—C(6) | −1.2 (4) |
O(1)—P(1)—C(3)—C(4) | −56.4 (2) | C(3)—C(4)—C(9)—C(8) | −178.8 (3) |
C(10)—P(1)—C(3)—C(2) | −114.2 (2) | C(5)—C(4)—C(9)—C(8) | 1.8 (4) |
C(10)—P(1)—C(3)—C(4) | 67.3 (2) | C(4)—C(5)—C(6)—C(7) | 0.5 (5) |
C(16)—P(1)—C(3)—C(2) | −0.6 (2) | C(5)—C(6)—C(7)—C(8) | −0.4 (6) |
C(16)—P(1)—C(3)—C(4) | −179.1 (2) | C(6)—C(7)—C(8)—C(9) | 1.1 (6) |
O(1)—P(1)—C(10)—C(11) | −21.1 (3) | C(7)—C(8)—C(9)—C(4) | −1.8 (5) |
O(1)—P(1)—C(10)—C(15) | 159.4 (2) | P(1)—C(10)—C(11)—C(12) | −179.5 (3) |
C(3)—P(1)—C(10)—C(11) | −145.8 (2) | C(15)—C(10)—C(11)—C(12) | 0.0 (4) |
C(3)—P(1)—C(10)—C(15) | 34.7 (3) | P(1)—C(10)—C(15)—C(14) | 179.5 (3) |
C(16)—P(1)—C(10)—C(11) | 101.5 (2) | C(11)—C(10)—C(15)—C(14) | −0.0 (4) |
C(16)—P(1)—C(10)—C(15) | −78.0 (3) | C(10)—C(11)—C(12)—C(13) | −0.6 (5) |
O(1)—P(1)—C(16)—C(17) | −14.9 (3) | C(11)—C(12)—C(13)—C(14) | 1.1 (6) |
O(1)—P(1)—C(16)—C(21) | 164.7 (2) | C(12)—C(13)—C(14)—C(15) | −1.1 (6) |
C(3)—P(1)—C(16)—C(17) | 109.4 (2) | C(13)—C(14)—C(15)—C(10) | 0.5 (5) |
C(3)—P(1)—C(16)—C(21) | −71.0 (3) | P(1)—C(16)—C(17)—C(18) | 179.9 (3) |
C(10)—P(1)—C(16)—C(17) | −138.1 (2) | C(21)—C(16)—C(17)—C(18) | 0.3 (5) |
C(10)—P(1)—C(16)—C(21) | 41.5 (3) | P(1)—C(16)—C(21)—C(20) | −179.1 (3) |
P(1)—C(3)—C(4)—C(5) | 176.9 (2) | C(17)—C(16)—C(21)—C(20) | 0.4 (5) |
P(1)—C(3)—C(4)—C(9) | −2.5 (4) | C(16)—C(17)—C(18)—C(19) | −0.9 (6) |
C(2)—C(3)—C(4)—C(5) | −1.5 (4) | C(17)—C(18)—C(19)—C(20) | 0.9 (7) |
C(2)—C(3)—C(4)—C(9) | 179.1 (3) | C(18)—C(19)—C(20)—C(21) | −0.2 (5) |
C(3)—C(4)—C(5)—C(6) | 179.4 (3) | C(19)—C(20)—C(21)—C(16) | −0.5 (6) |
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