Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619016619/yo3071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016619/yo3071Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016619/yo3071IIsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619016619/yo3071sup4.pdf |
CCDC references: 1971119; 1895358
Data collection: CrysAlis PRO (Rigaku OD, 2015) for (I); Rigaku CrystalClear-SM Expert (Rigaku, 2011) for (II). For both structures, cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (I); SHELXT2014 (Sheldrick, 2015a) for (II). Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for (I); SHELXL2018 (Sheldrick, 2015b) for (II). For both structures, molecular graphics: CAMERON (Watkin et al., 1996) and pyMOL (Schrödinger, 2015). Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) for (I); SHELXL2018 (Sheldrick, 2015b) for (II).
C19H24NO3P | F(000) = 736 |
Mr = 345.36 | Dx = 1.295 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3874 reflections |
a = 9.3538 (2) Å | θ = 2.1–27.1° |
b = 9.7899 (3) Å | µ = 0.17 mm−1 |
c = 19.3432 (5) Å | T = 175 K |
V = 1771.31 (5) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
Rigaku Xcalibur Sapphire3 Gemini diffractometer | 3411 independent reflections |
Graphite monochromator | 2964 reflections with I > 2.0σ(I) |
Detector resolution: 16.0143 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 28.0°, θmin = 2.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −7→12 |
Tmin = 0.979, Tmax = 1.000 | k = −9→11 |
9026 measured reflections | l = −23→23 |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.052 | Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince,
1982)
[weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 19.6 25.7 7.98 |
wR(F2) = 0.103 | (Δ/σ)max = 0.001 |
S = 0.95 | Δρmax = 0.32 e Å−3 |
3338 reflections | Δρmin = −0.54 e Å−3 |
221 parameters | Absolute structure: Flack (1983), 1505 Friedel-pairs |
79 restraints | Absolute structure parameter: 0.6 (3) |
Primary atom site location: iterative |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. |
Refinement. Data collection and crystal screening for (I) was performed on a Rigaku Oxford-Diffraction Gemini-S diffractometer with sealed-tube Mo-Kα radiation using the CrysAlisPro program (Rigaku Oxford-Diffraction, 2012). This program was also used for the integration of the data using default parameters, for the empirical absorption correction using spherical harmonics employing symmetry-equivalent and redundant data, and the correction for Lorentz and polarization effects. The ab-initio iterative charge flipping method was used to solve the crystal structure of (I) with parameters described elsewhere (van der Lee, 2013) employing the Superflip program (Palatinus&Chapuis, 2007) and it was refined using full-matrix least-squares procedures on squared structure factor amplitudes F2 as implemented in CRYSTALS (Betteridge et al., 2003) using all independent reflections with I>0. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.35676 (6) | 0.84662 (6) | 0.00163 (13) | 0.0183 | |
O2 | 0.4415 (4) | 0.9225 (3) | 0.06247 (18) | 0.0205 | |
C3 | 0.4113 (6) | 0.8932 (5) | 0.1321 (3) | 0.0257 | |
C4 | 0.4887 (6) | 0.7907 (5) | 0.1653 (2) | 0.0305 | |
C5 | 0.4633 (8) | 0.7722 (6) | 0.2345 (3) | 0.0433 | |
C6 | 0.3634 (7) | 0.8486 (7) | 0.2706 (3) | 0.0431 | |
C7 | 0.2905 (8) | 0.9495 (7) | 0.2365 (3) | 0.0406 | |
C8 | 0.3173 (7) | 0.9711 (6) | 0.1665 (3) | 0.0333 | |
H81 | 0.2689 | 1.0405 | 0.1435 | 0.0500* | |
H71 | 0.2237 | 1.0015 | 0.2605 | 0.0500* | |
H61 | 0.3472 | 0.8316 | 0.3172 | 0.0500* | |
H51 | 0.5151 | 0.7058 | 0.2580 | 0.0500* | |
H41 | 0.5550 | 0.7374 | 0.1417 | 0.0500* | |
O9 | 0.20228 (18) | 0.87095 (18) | 0.0010 (3) | 0.0275 | |
O10 | 0.4444 (4) | 0.9209 (4) | −0.0573 (2) | 0.0288 | |
C11 | 0.4140 (5) | 0.8929 (5) | −0.1266 (3) | 0.0223 | |
C12 | 0.3098 (6) | 0.9729 (6) | −0.1603 (3) | 0.0323 | |
C13 | 0.2900 (8) | 0.9499 (8) | −0.2298 (3) | 0.0459 | |
C14 | 0.3672 (7) | 0.8504 (7) | −0.2635 (4) | 0.0488 | |
C15 | 0.4657 (7) | 0.7703 (7) | −0.2302 (3) | 0.0420 | |
C16 | 0.4909 (7) | 0.7958 (6) | −0.1596 (2) | 0.0358 | |
H161 | 0.5592 | 0.7455 | −0.1357 | 0.0500* | |
H151 | 0.5141 | 0.7017 | −0.2538 | 0.0500* | |
H141 | 0.3519 | 0.8376 | −0.3106 | 0.0500* | |
H131 | 0.2239 | 1.0023 | −0.2540 | 0.0500* | |
N17 | 0.3982 (2) | 0.6874 (2) | 0.0026 (3) | 0.0213 | |
C18 | 0.2936 (3) | 0.5742 (2) | 0.0018 (3) | 0.0232 | |
C19 | 0.3086 (7) | 0.4933 (6) | 0.0682 (3) | 0.0425 | |
C20 | 0.4369 (7) | 0.3947 (6) | 0.0702 (3) | 0.0671 | |
C21 | 0.4344 (6) | 0.2720 (4) | 0.0185 (3) | 0.0809 | |
C22 | 0.4727 (8) | 0.2979 (6) | −0.0558 (3) | 0.0828 | |
C23 | 0.4388 (6) | 0.4358 (5) | −0.0842 (3) | 0.0460 | |
C24 | 0.2980 (6) | 0.4913 (5) | −0.0638 (3) | 0.0330 | |
H241 | 0.2705 | 0.5513 | −0.1015 | 0.0500* | |
H242 | 0.2268 | 0.4196 | −0.0609 | 0.0500* | |
H231 | 0.4456 | 0.4317 | −0.1342 | 0.0500* | |
H232 | 0.5135 | 0.4971 | −0.0684 | 0.0500* | |
H191 | 0.2225 | 0.4394 | 0.0742 | 0.0500* | |
H192 | 0.3146 | 0.5558 | 0.1070 | 0.0500* | |
H181 | 0.1988 | 0.6165 | 0.0040 | 0.0500* | |
H201 | 0.5191 | 0.4478 | 0.0598 | 0.0830* | |
H202 | 0.4452 | 0.3584 | 0.1155 | 0.0830* | |
H211 | 0.4991 | 0.2058 | 0.0360 | 0.1300* | |
H212 | 0.3399 | 0.2364 | 0.0198 | 0.1300* | |
H221 | 0.5721 | 0.2813 | −0.0614 | 0.1047* | |
H222 | 0.4199 | 0.2331 | −0.0820 | 0.1047* | |
H121 | 0.2592 | 1.0429 | −0.1367 | 0.0436* | |
H171 | 0.484 (2) | 0.6673 (19) | −0.009 (2) | 0.0300* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0138 (3) | 0.0183 (3) | 0.0227 (3) | −0.0001 (2) | 0.0006 (7) | −0.0007 (6) |
O2 | 0.0227 (17) | 0.0164 (13) | 0.0223 (15) | −0.0076 (15) | −0.0063 (14) | −0.0020 (13) |
C3 | 0.029 (3) | 0.028 (2) | 0.020 (2) | −0.011 (2) | 0.002 (2) | −0.007 (2) |
C4 | 0.029 (3) | 0.024 (2) | 0.039 (3) | 0.008 (2) | −0.011 (2) | −0.003 (2) |
C5 | 0.055 (5) | 0.042 (3) | 0.033 (3) | 0.005 (3) | −0.014 (3) | 0.002 (3) |
C6 | 0.058 (5) | 0.055 (4) | 0.016 (3) | −0.018 (3) | 0.004 (3) | 0.003 (2) |
C7 | 0.045 (4) | 0.044 (3) | 0.033 (3) | 0.005 (3) | 0.018 (3) | −0.015 (3) |
C8 | 0.037 (3) | 0.034 (3) | 0.029 (3) | 0.006 (2) | 0.010 (2) | −0.007 (2) |
O9 | 0.0155 (8) | 0.0237 (9) | 0.0434 (11) | 0.0019 (7) | −0.004 (2) | −0.006 (2) |
O10 | 0.027 (2) | 0.0371 (17) | 0.0223 (15) | −0.0064 (19) | −0.0090 (16) | 0.0040 (15) |
C11 | 0.016 (3) | 0.026 (2) | 0.025 (2) | −0.003 (2) | 0.002 (2) | 0.003 (2) |
C12 | 0.023 (3) | 0.034 (3) | 0.040 (3) | −0.003 (2) | 0.003 (2) | 0.005 (3) |
C13 | 0.038 (4) | 0.058 (4) | 0.042 (3) | −0.011 (4) | −0.011 (3) | 0.012 (3) |
C14 | 0.043 (5) | 0.069 (5) | 0.034 (4) | −0.011 (3) | −0.009 (3) | 0.015 (3) |
C15 | 0.039 (4) | 0.055 (4) | 0.032 (3) | −0.008 (3) | 0.005 (3) | −0.010 (3) |
C16 | 0.036 (3) | 0.052 (3) | 0.020 (3) | −0.004 (3) | −0.008 (2) | 0.004 (2) |
N17 | 0.0128 (9) | 0.0206 (10) | 0.0305 (12) | 0.0018 (8) | 0.003 (3) | −0.006 (2) |
C18 | 0.0189 (12) | 0.0192 (12) | 0.0316 (13) | −0.0034 (10) | 0.008 (2) | 0.001 (2) |
C19 | 0.057 (3) | 0.040 (2) | 0.030 (2) | −0.018 (2) | 0.011 (3) | 0.007 (2) |
C20 | 0.056 (3) | 0.071 (3) | 0.074 (3) | −0.007 (3) | −0.019 (3) | 0.047 (2) |
C21 | 0.058 (3) | 0.0235 (17) | 0.161 (4) | 0.0095 (18) | 0.021 (4) | 0.037 (2) |
C22 | 0.065 (4) | 0.052 (2) | 0.131 (4) | 0.018 (3) | 0.001 (3) | −0.013 (2) |
C23 | 0.039 (2) | 0.053 (2) | 0.046 (2) | 0.002 (2) | −0.002 (2) | −0.0226 (17) |
C24 | 0.029 (2) | 0.036 (2) | 0.034 (2) | −0.006 (2) | −0.001 (2) | −0.0073 (19) |
P1—O2 | 1.601 (3) | C15—C16 | 1.409 (6) |
P1—O9 | 1.4645 (18) | C15—H151 | 0.930 |
P1—O10 | 1.581 (4) | C16—H161 | 0.930 |
P1—N17 | 1.607 (2) | N17—C18 | 1.479 (3) |
O2—C3 | 1.405 (6) | N17—H171 | 0.860 (18) |
C3—C4 | 1.394 (6) | C18—C19 | 1.514 (6) |
C3—C8 | 1.341 (7) | C18—C24 | 1.507 (6) |
C4—C5 | 1.371 (6) | C18—H181 | 0.980 |
C4—H41 | 0.930 | C19—C20 | 1.540 (7) |
C5—C6 | 1.385 (7) | C19—H191 | 0.970 |
C5—H51 | 0.930 | C19—H192 | 0.970 |
C6—C7 | 1.369 (7) | C20—C21 | 1.563 (6) |
C6—H61 | 0.930 | C20—H201 | 0.950 |
C7—C8 | 1.394 (6) | C20—H202 | 0.950 |
C7—H71 | 0.930 | C21—C22 | 1.502 (7) |
C8—H81 | 0.930 | C21—H211 | 0.950 |
O10—C11 | 1.399 (6) | C21—H212 | 0.950 |
C11—C12 | 1.409 (6) | C22—C23 | 1.491 (6) |
C11—C16 | 1.351 (7) | C22—H221 | 0.950 |
C12—C13 | 1.377 (6) | C22—H222 | 0.950 |
C12—H121 | 0.950 | C23—C24 | 1.478 (6) |
C13—C14 | 1.377 (7) | C23—H231 | 0.970 |
C13—H131 | 0.930 | C23—H232 | 0.970 |
C14—C15 | 1.370 (7) | C24—H241 | 0.970 |
C14—H141 | 0.930 | C24—H242 | 0.970 |
O2—P1—O9 | 114.8 (3) | P1—N17—H171 | 116.4 (13) |
O2—P1—O10 | 93.42 (10) | C18—N17—H171 | 116.5 (13) |
O9—P1—O10 | 115.5 (3) | N17—C18—C19 | 108.8 (4) |
O2—P1—N17 | 108.8 (2) | N17—C18—C24 | 113.2 (4) |
O9—P1—N17 | 113.34 (11) | C19—C18—C24 | 115.5 (2) |
O10—P1—N17 | 109.2 (2) | N17—C18—H181 | 106.4 |
P1—O2—C3 | 120.7 (3) | C19—C18—H181 | 105.6 |
O2—C3—C4 | 118.9 (5) | C24—C18—H181 | 106.8 |
O2—C3—C8 | 119.4 (5) | C18—C19—C20 | 114.9 (5) |
C4—C3—C8 | 121.4 (5) | C18—C19—H191 | 108.0 |
C3—C4—C5 | 117.0 (5) | C20—C19—H191 | 107.6 |
C3—C4—H41 | 121.7 | C18—C19—H192 | 109.3 |
C5—C4—H41 | 121.3 | C20—C19—H192 | 109.3 |
C4—C5—C6 | 122.5 (6) | H191—C19—H192 | 107.4 |
C4—C5—H51 | 118.6 | C19—C20—C21 | 117.0 (5) |
C6—C5—H51 | 118.8 | C19—C20—H201 | 106.3 |
C5—C6—C7 | 118.9 (6) | C21—C20—H201 | 107.4 |
C5—C6—H61 | 120.2 | C19—C20—H202 | 108.8 |
C7—C6—H61 | 120.9 | C21—C20—H202 | 107.8 |
C6—C7—C8 | 119.2 (6) | H201—C20—H202 | 109.5 |
C6—C7—H71 | 119.4 | C20—C21—C22 | 118.6 (4) |
C8—C7—H71 | 121.4 | C20—C21—H211 | 106.6 |
C7—C8—C3 | 120.9 (6) | C22—C21—H211 | 107.8 |
C7—C8—H81 | 119.3 | C20—C21—H212 | 106.2 |
C3—C8—H81 | 119.8 | C22—C21—H212 | 108.0 |
P1—O10—C11 | 119.7 (3) | H211—C21—H212 | 109.5 |
O10—C11—C12 | 118.3 (5) | C21—C22—C23 | 117.0 (5) |
O10—C11—C16 | 118.8 (5) | C21—C22—H221 | 108.2 |
C12—C11—C16 | 122.8 (5) | C23—C22—H221 | 108.7 |
C11—C12—C13 | 116.9 (6) | C21—C22—H222 | 105.8 |
C11—C12—H121 | 121.6 | C23—C22—H222 | 107.4 |
C13—C12—H121 | 121.4 | H221—C22—H222 | 109.5 |
C12—C13—C14 | 120.5 (7) | C22—C23—C24 | 115.1 (5) |
C12—C13—H131 | 119.4 | C22—C23—H231 | 108.4 |
C14—C13—H131 | 120.1 | C24—C23—H231 | 109.8 |
C13—C14—C15 | 122.4 (7) | C22—C23—H232 | 106.9 |
C13—C14—H141 | 118.5 | C24—C23—H232 | 109.3 |
C15—C14—H141 | 119.1 | H231—C23—H232 | 107.1 |
C14—C15—C16 | 117.8 (6) | C18—C24—C23 | 116.5 (4) |
C14—C15—H151 | 120.6 | C18—C24—H241 | 107.4 |
C16—C15—H151 | 121.6 | C23—C24—H241 | 105.0 |
C15—C16—C11 | 119.6 (6) | C18—C24—H242 | 108.8 |
C15—C16—H161 | 120.2 | C23—C24—H242 | 111.2 |
C11—C16—H161 | 120.2 | H241—C24—H242 | 107.4 |
P1—N17—C18 | 124.57 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H232···O9i | 0.97 | 2.57 | 3.516 (8) | 166 (1) |
N17—H171···O9i | 0.86 | 2.08 | 2.901 (8) | 159 (4) |
Symmetry code: (i) x+1/2, −y+3/2, z. |
C26H24NO3P | Z = 2 |
Mr = 429.43 | F(000) = 452 |
Triclinic, P1 | Dx = 1.320 Mg m−3 |
a = 8.3404 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5349 (5) Å | Cell parameters from 7627 reflections |
c = 14.9677 (7) Å | θ = 3.7–29.8° |
α = 76.280 (4)° | µ = 0.16 mm−1 |
β = 75.778 (4)° | T = 120 K |
γ = 72.055 (4)° | Block, colourless |
V = 1080.73 (9) Å3 | 0.25 × 0.20 × 0.20 mm |
AFC11 (Right): Eulerian 3 circle CCD diffractometer | 3578 reflections with I > 2σ(I) |
Radiation source: Rotating Anode MicroMax-007HF DW 1.2 kW | Rint = 0.018 |
Profile data from ω–scans | θmax = 25.4°, θmin = 3.2° |
Absorption correction: multi-scan CrysAlis PRO (Rigaku OD, 2015) | h = −10→10 |
Tmin = 0.722, Tmax = 1.000 | k = −11→11 |
9523 measured reflections | l = −18→18 |
3901 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0421P)2 + 0.4112P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.021 |
3901 reflections | Δρmax = 0.27 e Å−3 |
280 parameters | Δρmin = −0.34 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Data collection and crystal screening for (I) was performed on a Rigaku Oxford-Diffraction Gemini-S diffractometer with sealed-tube Mo-Kα radiation using the CrysAlisPro program (Rigaku Oxford-Diffraction, 2012). This program was also used for the integration of the data using default parameters, for the empirical absorption correction using spherical harmonics employing symmetry-equivalent and redundant data, and the correction for Lorentz and polarization effects. The ab-initio iterative charge flipping method was used to solve the crystal structure of (I) with parameters described elsewhere (van der Lee, 2013) employing the Superflip program (Palatinus&Chapuis, 2007) and it was refined using full-matrix least-squares procedures on squared structure factor amplitudes F2 as implemented in CRYSTALS (Betteridge et al., 2003) using all independent reflections with I>0. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.28992 (4) | 0.22585 (4) | 0.24553 (2) | 0.02034 (11) | |
O1 | 0.19646 (12) | 0.25264 (11) | 0.16998 (7) | 0.0268 (2) | |
O2 | 0.18570 (12) | 0.30054 (10) | 0.33444 (6) | 0.0242 (2) | |
O3 | 0.44766 (12) | 0.29786 (10) | 0.22264 (6) | 0.0229 (2) | |
N1 | 0.35880 (14) | 0.04977 (12) | 0.28829 (7) | 0.0210 (2) | |
C1 | 0.11701 (16) | 0.45642 (14) | 0.32925 (9) | 0.0216 (3) | |
C2 | 0.13891 (17) | 0.51758 (16) | 0.39864 (9) | 0.0251 (3) | |
H2A | 0.204474 | 0.457320 | 0.444418 | 0.030* | |
C3 | 0.06359 (18) | 0.66858 (16) | 0.40047 (10) | 0.0283 (3) | |
H3A | 0.077787 | 0.712423 | 0.447789 | 0.034* | |
C4 | −0.03204 (17) | 0.75573 (15) | 0.33386 (10) | 0.0279 (3) | |
H4A | −0.083810 | 0.859051 | 0.335667 | 0.033* | |
C5 | −0.05239 (18) | 0.69265 (16) | 0.26462 (10) | 0.0287 (3) | |
H5A | −0.117877 | 0.752952 | 0.218813 | 0.034* | |
C6 | 0.02249 (17) | 0.54132 (15) | 0.26162 (10) | 0.0264 (3) | |
H6A | 0.008991 | 0.497327 | 0.214182 | 0.032* | |
C7 | 0.58266 (16) | 0.26177 (14) | 0.14702 (9) | 0.0212 (3) | |
C8 | 0.55543 (18) | 0.31321 (15) | 0.05655 (9) | 0.0244 (3) | |
H8A | 0.444962 | 0.369332 | 0.044181 | 0.029* | |
C9 | 0.69321 (19) | 0.28115 (17) | −0.01621 (10) | 0.0311 (3) | |
H9A | 0.677120 | 0.314654 | −0.079222 | 0.037* | |
C10 | 0.8537 (2) | 0.2007 (2) | 0.00263 (11) | 0.0385 (4) | |
H10A | 0.947575 | 0.179286 | −0.047458 | 0.046* | |
C11 | 0.8781 (2) | 0.1512 (2) | 0.09426 (11) | 0.0395 (4) | |
H11A | 0.988814 | 0.096637 | 0.106884 | 0.047* | |
C12 | 0.74155 (18) | 0.18102 (16) | 0.16751 (10) | 0.0287 (3) | |
H12A | 0.756938 | 0.146579 | 0.230603 | 0.034* | |
C13 | 0.31490 (17) | −0.06607 (15) | 0.25673 (9) | 0.0241 (3) | |
H13A | 0.224230 | −0.017085 | 0.218789 | 0.029* | |
H13B | 0.267326 | −0.131358 | 0.312238 | 0.029* | |
C14 | 0.46539 (17) | −0.16227 (15) | 0.19938 (9) | 0.0227 (3) | |
C15 | 0.55410 (18) | −0.09884 (15) | 0.11602 (10) | 0.0256 (3) | |
H15A | 0.524078 | 0.006721 | 0.096448 | 0.031* | |
C16 | 0.68566 (19) | −0.18823 (18) | 0.06139 (11) | 0.0334 (3) | |
H16A | 0.744928 | −0.144031 | 0.004279 | 0.040* | |
C17 | 0.7312 (2) | −0.34247 (19) | 0.08992 (12) | 0.0399 (4) | |
H17A | 0.821881 | −0.403902 | 0.052550 | 0.048* | |
C18 | 0.6445 (2) | −0.40617 (17) | 0.17262 (13) | 0.0389 (4) | |
H18A | 0.675686 | −0.511682 | 0.192324 | 0.047* | |
C19 | 0.5118 (2) | −0.31677 (15) | 0.22719 (11) | 0.0302 (3) | |
H19A | 0.452266 | −0.361485 | 0.284001 | 0.036* | |
C20 | 0.47160 (16) | −0.00427 (14) | 0.35785 (9) | 0.0215 (3) | |
H20A | 0.491704 | 0.082604 | 0.374481 | 0.026* | |
H20B | 0.583807 | −0.065766 | 0.329936 | 0.026* | |
C21 | 0.39591 (16) | −0.09676 (14) | 0.44588 (9) | 0.0209 (3) | |
C22 | 0.48106 (18) | −0.24494 (16) | 0.47433 (10) | 0.0274 (3) | |
H22A | 0.589320 | −0.288210 | 0.439166 | 0.033* | |
C23 | 0.4090 (2) | −0.33073 (16) | 0.55406 (11) | 0.0327 (3) | |
H23A | 0.468936 | −0.431673 | 0.573441 | 0.039* | |
C24 | 0.2508 (2) | −0.26933 (17) | 0.60496 (10) | 0.0303 (3) | |
H24A | 0.200719 | −0.328244 | 0.658723 | 0.036* | |
C25 | 0.16556 (18) | −0.12152 (17) | 0.57722 (10) | 0.0281 (3) | |
H25A | 0.056824 | −0.078855 | 0.612209 | 0.034* | |
C26 | 0.23788 (17) | −0.03546 (15) | 0.49876 (9) | 0.0242 (3) | |
H26A | 0.179122 | 0.066360 | 0.480840 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01953 (18) | 0.02070 (19) | 0.01905 (18) | −0.00377 (13) | −0.00332 (13) | −0.00256 (13) |
O1 | 0.0258 (5) | 0.0293 (5) | 0.0242 (5) | −0.0051 (4) | −0.0080 (4) | −0.0022 (4) |
O2 | 0.0241 (5) | 0.0209 (5) | 0.0218 (5) | −0.0006 (4) | −0.0015 (4) | −0.0026 (4) |
O3 | 0.0243 (5) | 0.0224 (5) | 0.0217 (5) | −0.0070 (4) | −0.0007 (4) | −0.0062 (4) |
N1 | 0.0220 (5) | 0.0211 (6) | 0.0214 (5) | −0.0054 (4) | −0.0068 (4) | −0.0039 (4) |
C1 | 0.0166 (6) | 0.0214 (6) | 0.0229 (6) | −0.0039 (5) | 0.0013 (5) | −0.0032 (5) |
C2 | 0.0198 (6) | 0.0310 (7) | 0.0223 (7) | −0.0059 (5) | −0.0021 (5) | −0.0035 (6) |
C3 | 0.0255 (7) | 0.0319 (7) | 0.0292 (7) | −0.0098 (6) | −0.0009 (6) | −0.0103 (6) |
C4 | 0.0235 (7) | 0.0232 (7) | 0.0357 (8) | −0.0059 (5) | −0.0017 (6) | −0.0072 (6) |
C5 | 0.0257 (7) | 0.0253 (7) | 0.0316 (8) | −0.0027 (6) | −0.0077 (6) | −0.0014 (6) |
C6 | 0.0260 (7) | 0.0261 (7) | 0.0265 (7) | −0.0038 (6) | −0.0065 (6) | −0.0059 (6) |
C7 | 0.0236 (7) | 0.0189 (6) | 0.0220 (6) | −0.0085 (5) | −0.0007 (5) | −0.0056 (5) |
C8 | 0.0256 (7) | 0.0230 (7) | 0.0251 (7) | −0.0087 (5) | −0.0058 (5) | −0.0012 (5) |
C9 | 0.0336 (8) | 0.0394 (8) | 0.0220 (7) | −0.0149 (6) | −0.0033 (6) | −0.0039 (6) |
C10 | 0.0283 (8) | 0.0575 (10) | 0.0280 (8) | −0.0113 (7) | 0.0033 (6) | −0.0130 (7) |
C11 | 0.0228 (7) | 0.0564 (10) | 0.0349 (8) | −0.0029 (7) | −0.0048 (6) | −0.0100 (7) |
C12 | 0.0274 (7) | 0.0349 (8) | 0.0237 (7) | −0.0071 (6) | −0.0068 (6) | −0.0045 (6) |
C13 | 0.0262 (7) | 0.0250 (7) | 0.0248 (7) | −0.0112 (5) | −0.0067 (5) | −0.0035 (5) |
C14 | 0.0272 (7) | 0.0221 (6) | 0.0236 (7) | −0.0088 (5) | −0.0105 (5) | −0.0043 (5) |
C15 | 0.0297 (7) | 0.0246 (7) | 0.0247 (7) | −0.0080 (6) | −0.0082 (6) | −0.0042 (5) |
C16 | 0.0297 (8) | 0.0454 (9) | 0.0289 (8) | −0.0093 (7) | −0.0061 (6) | −0.0139 (7) |
C17 | 0.0337 (8) | 0.0429 (9) | 0.0492 (10) | 0.0049 (7) | −0.0182 (7) | −0.0290 (8) |
C18 | 0.0472 (9) | 0.0217 (7) | 0.0557 (10) | −0.0003 (7) | −0.0299 (8) | −0.0121 (7) |
C19 | 0.0406 (8) | 0.0224 (7) | 0.0341 (8) | −0.0122 (6) | −0.0180 (7) | −0.0009 (6) |
C20 | 0.0202 (6) | 0.0219 (6) | 0.0225 (6) | −0.0043 (5) | −0.0064 (5) | −0.0034 (5) |
C21 | 0.0224 (6) | 0.0222 (6) | 0.0207 (6) | −0.0065 (5) | −0.0073 (5) | −0.0042 (5) |
C22 | 0.0256 (7) | 0.0264 (7) | 0.0276 (7) | −0.0031 (6) | −0.0061 (6) | −0.0036 (6) |
C23 | 0.0378 (8) | 0.0240 (7) | 0.0338 (8) | −0.0063 (6) | −0.0127 (7) | 0.0031 (6) |
C24 | 0.0366 (8) | 0.0352 (8) | 0.0230 (7) | −0.0183 (6) | −0.0067 (6) | 0.0003 (6) |
C25 | 0.0266 (7) | 0.0367 (8) | 0.0237 (7) | −0.0104 (6) | −0.0033 (6) | −0.0090 (6) |
C26 | 0.0252 (7) | 0.0236 (7) | 0.0242 (7) | −0.0047 (5) | −0.0063 (5) | −0.0054 (5) |
P1—O1 | 1.4578 (10) | C12—H12A | 0.9500 |
P1—O2 | 1.5916 (9) | C13—C14 | 1.5127 (18) |
P1—O3 | 1.5948 (10) | C13—H13A | 0.9900 |
P1—N1 | 1.6232 (11) | C13—H13B | 0.9900 |
O2—C1 | 1.4092 (15) | C14—C19 | 1.3893 (19) |
O3—C7 | 1.4096 (15) | C14—C15 | 1.3907 (19) |
N1—C13 | 1.4693 (17) | C15—C16 | 1.383 (2) |
N1—C20 | 1.4707 (17) | C15—H15A | 0.9500 |
C1—C2 | 1.378 (2) | C16—C17 | 1.388 (2) |
C1—C6 | 1.3826 (19) | C16—H16A | 0.9500 |
C2—C3 | 1.386 (2) | C17—C18 | 1.378 (3) |
C2—H2A | 0.9500 | C17—H17A | 0.9500 |
C3—C4 | 1.382 (2) | C18—C19 | 1.387 (2) |
C3—H3A | 0.9500 | C18—H18A | 0.9500 |
C4—C5 | 1.382 (2) | C19—H19A | 0.9500 |
C4—H4A | 0.9500 | C20—C21 | 1.5151 (18) |
C5—C6 | 1.3913 (19) | C20—H20A | 0.9900 |
C5—H5A | 0.9500 | C20—H20B | 0.9900 |
C6—H6A | 0.9500 | C21—C22 | 1.3881 (19) |
C7—C8 | 1.3760 (19) | C21—C26 | 1.3919 (18) |
C7—C12 | 1.3791 (19) | C22—C23 | 1.393 (2) |
C8—C9 | 1.3880 (19) | C22—H22A | 0.9500 |
C8—H8A | 0.9500 | C23—C24 | 1.381 (2) |
C9—C10 | 1.382 (2) | C23—H23A | 0.9500 |
C9—H9A | 0.9500 | C24—C25 | 1.384 (2) |
C10—C11 | 1.384 (2) | C24—H24A | 0.9500 |
C10—H10A | 0.9500 | C25—C26 | 1.384 (2) |
C11—C12 | 1.384 (2) | C25—H25A | 0.9500 |
C11—H11A | 0.9500 | C26—H26A | 0.9500 |
O1—P1—O2 | 115.77 (5) | N1—C13—H13A | 108.8 |
O1—P1—O3 | 116.27 (5) | C14—C13—H13A | 108.8 |
O2—P1—O3 | 97.78 (5) | N1—C13—H13B | 108.8 |
O1—P1—N1 | 113.54 (6) | C14—C13—H13B | 108.8 |
O2—P1—N1 | 104.31 (5) | H13A—C13—H13B | 107.7 |
O3—P1—N1 | 107.44 (5) | C19—C14—C15 | 118.94 (13) |
C1—O2—P1 | 122.79 (8) | C19—C14—C13 | 120.19 (12) |
C7—O3—P1 | 119.73 (8) | C15—C14—C13 | 120.80 (12) |
C13—N1—C20 | 115.99 (10) | C16—C15—C14 | 120.52 (13) |
C13—N1—P1 | 121.10 (9) | C16—C15—H15A | 119.7 |
C20—N1—P1 | 122.88 (9) | C14—C15—H15A | 119.7 |
C2—C1—C6 | 121.90 (12) | C15—C16—C17 | 120.07 (15) |
C2—C1—O2 | 116.55 (12) | C15—C16—H16A | 120.0 |
C6—C1—O2 | 121.40 (12) | C17—C16—H16A | 120.0 |
C1—C2—C3 | 118.83 (13) | C18—C17—C16 | 119.78 (14) |
C1—C2—H2A | 120.6 | C18—C17—H17A | 120.1 |
C3—C2—H2A | 120.6 | C16—C17—H17A | 120.1 |
C4—C3—C2 | 120.38 (14) | C17—C18—C19 | 120.22 (14) |
C4—C3—H3A | 119.8 | C17—C18—H18A | 119.9 |
C2—C3—H3A | 119.8 | C19—C18—H18A | 119.9 |
C5—C4—C3 | 120.03 (13) | C18—C19—C14 | 120.47 (14) |
C5—C4—H4A | 120.0 | C18—C19—H19A | 119.8 |
C3—C4—H4A | 120.0 | C14—C19—H19A | 119.8 |
C4—C5—C6 | 120.37 (13) | N1—C20—C21 | 112.18 (10) |
C4—C5—H5A | 119.8 | N1—C20—H20A | 109.2 |
C6—C5—H5A | 119.8 | C21—C20—H20A | 109.2 |
C1—C6—C5 | 118.49 (13) | N1—C20—H20B | 109.2 |
C1—C6—H6A | 120.8 | C21—C20—H20B | 109.2 |
C5—C6—H6A | 120.8 | H20A—C20—H20B | 107.9 |
C8—C7—C12 | 122.33 (12) | C22—C21—C26 | 118.74 (12) |
C8—C7—O3 | 120.00 (12) | C22—C21—C20 | 120.71 (12) |
C12—C7—O3 | 117.59 (12) | C26—C21—C20 | 120.54 (11) |
C7—C8—C9 | 118.41 (13) | C21—C22—C23 | 120.54 (13) |
C7—C8—H8A | 120.8 | C21—C22—H22A | 119.7 |
C9—C8—H8A | 120.8 | C23—C22—H22A | 119.7 |
C10—C9—C8 | 120.28 (14) | C24—C23—C22 | 120.13 (13) |
C10—C9—H9A | 119.9 | C24—C23—H23A | 119.9 |
C8—C9—H9A | 119.9 | C22—C23—H23A | 119.9 |
C9—C10—C11 | 120.20 (14) | C23—C24—C25 | 119.63 (13) |
C9—C10—H10A | 119.9 | C23—C24—H24A | 120.2 |
C11—C10—H10A | 119.9 | C25—C24—H24A | 120.2 |
C12—C11—C10 | 120.16 (14) | C24—C25—C26 | 120.35 (13) |
C12—C11—H11A | 119.9 | C24—C25—H25A | 119.8 |
C10—C11—H11A | 119.9 | C26—C25—H25A | 119.8 |
C7—C12—C11 | 118.61 (13) | C25—C26—C21 | 120.60 (13) |
C7—C12—H12A | 120.7 | C25—C26—H26A | 119.7 |
C11—C12—H12A | 120.7 | C21—C26—H26A | 119.7 |
N1—C13—C14 | 113.73 (11) |
Cg1, Cg2 and Cg1 are the centroids of the C1–C6, C14–C19 and C7–C12 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···CG1i | 0.95 | 3.50 | 3.9798 (13) | 114 |
C13—H13B···CG1ii | 0.99 | 3.49 | 4.2048 (13) | 131 |
C18—H18A···CG3ii | 0.95 | 3.22 | 3.8839 (15) | 128 |
C8—H8A···CG2iii | 0.95 | 3.41 | 3.7716 (14) | 106 |
C6—H6A···O1 | 0.95 | 2.51 | 3.1488 (17) | 125 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y−1, z; (iii) −x+1, −y, −z. |