Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011746/bt6060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011746/bt6060Isup2.hkl |
CCDC reference: 170907
The title compound was obtained from the Aldrich Chemical Company and recrystallized in a dry atmosphere via slow evaporation from dichloromethane.
The crystals were extremely hygroscopic and it was found necessary to mount and place them on the diffractometer under a constant stream of cold nitrogen gas. The resulting data set was of low quality and it was necessary to restrain the geometries of the tetrabutylammonium ions to be similar. The structure contains a non-spacegroup translation.
Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinoski & Minor, 1997), COLLECT; data reduction: DENZO (Otwinoski & Minor, 1997), COLLECT, maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS 97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL 97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).
C17.33H40.67Cl2.67NO4P | Z = 12 |
Mr = 452.68 | F(000) = 2928 |
Triclinic, P1 | Dx = 1.233 Mg m−3 |
a = 16.1733 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.8443 (3) Å | Cell parameters from 58198 reflections |
c = 26.7000 (5) Å | θ = 2.9–24.1° |
α = 77.520 (3)° | µ = 0.43 mm−1 |
β = 77.237 (3)° | T = 120 K |
γ = 83.124 (3)° | Block, colourless |
V = 7316.7 (2) Å3 | 0.50 × 0.15 × 0.10 mm |
Nonius Kappa CCD Area-detector diffractometer | 22291 independent reflections |
Radiation source: Nonius FR591 Rotating anode | 10322 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 9.091 pixels mm1 pixels mm-1 | θmax = 24.1°, θmin = 2.9° |
ϕ and ω scans to fill the Ewald sphere | h = −18→18 |
Absorption correction: multi-scans (SORTAV; Blessing, 1997) | k = −20→20 |
Tmin = 0.816, Tmax = 0.959 | l = −30→30 |
58198 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.156 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.393 | H-atom parameters constrained |
S = 1.93 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
22291 reflections | (Δ/σ)max = 2.834 |
1417 parameters | Δρmax = 2.66 e Å−3 |
878 restraints | Δρmin = −1.47 e Å−3 |
C17.33H40.67Cl2.67NO4P | γ = 83.124 (3)° |
Mr = 452.68 | V = 7316.7 (2) Å3 |
Triclinic, P1 | Z = 12 |
a = 16.1733 (3) Å | Mo Kα radiation |
b = 17.8443 (3) Å | µ = 0.43 mm−1 |
c = 26.7000 (5) Å | T = 120 K |
α = 77.520 (3)° | 0.50 × 0.15 × 0.10 mm |
β = 77.237 (3)° |
Nonius Kappa CCD Area-detector diffractometer | 22291 independent reflections |
Absorption correction: multi-scans (SORTAV; Blessing, 1997) | 10322 reflections with I > 2σ(I) |
Tmin = 0.816, Tmax = 0.959 | Rint = 0.100 |
58198 measured reflections | θmax = 24.1° |
R[F2 > 2σ(F2)] = 0.156 | 878 restraints |
wR(F2) = 0.393 | H-atom parameters constrained |
S = 1.93 | (Δ/σ)max = 2.834 |
22291 reflections | Δρmax = 2.66 e Å−3 |
1417 parameters | Δρmin = −1.47 e Å−3 |
Experimental. The crystals were extremely hygroscopic and it was necessary to mount and place them on the diffractometer under a constant stream of cold nitrogen. |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2200 (4) | 0.5218 (4) | 0.3025 (2) | 0.047 (2) | |
C1 | 0.2035 (5) | 0.4383 (4) | 0.3053 (3) | 0.041 (3) | |
H1A | 0.1914 | 0.4336 | 0.2714 | 0.049* | |
H1B | 0.2558 | 0.4051 | 0.3104 | 0.049* | |
C2 | 0.1313 (5) | 0.4091 (4) | 0.3482 (3) | 0.036 (3) | |
H2A | 0.0781 | 0.4405 | 0.3427 | 0.043* | |
H2B | 0.1422 | 0.4142 | 0.3823 | 0.043* | |
C3 | 0.1209 (5) | 0.3243 (4) | 0.3492 (4) | 0.048 (3) | |
H3A | 0.1155 | 0.3188 | 0.3139 | 0.058* | |
H3B | 0.1724 | 0.2927 | 0.3577 | 0.058* | |
C4 | 0.0426 (6) | 0.2943 (5) | 0.3894 (3) | 0.057 (3) | |
H4A | 0.0383 | 0.2402 | 0.3886 | 0.085* | |
H4B | −0.0087 | 0.3249 | 0.3808 | 0.085* | |
H4C | 0.0482 | 0.2986 | 0.4244 | 0.085* | |
C5 | 0.1401 (5) | 0.5740 (5) | 0.2932 (3) | 0.043 (3) | |
H5A | 0.0956 | 0.5637 | 0.3254 | 0.052* | |
H5B | 0.1537 | 0.6281 | 0.2883 | 0.052* | |
C6 | 0.1030 (6) | 0.5671 (5) | 0.2480 (3) | 0.065 (3) | |
H6A | 0.0783 | 0.5166 | 0.2558 | 0.078* | |
H6B | 0.1491 | 0.5681 | 0.2167 | 0.078* | |
C7 | 0.0351 (6) | 0.6298 (5) | 0.2358 (4) | 0.074 (4) | |
H7A | −0.0069 | 0.6334 | 0.2685 | 0.089* | |
H7B | 0.0052 | 0.6151 | 0.2112 | 0.089* | |
C8 | 0.0675 (8) | 0.7080 (5) | 0.2122 (4) | 0.086 (4) | |
H8A | 0.0195 | 0.7456 | 0.2064 | 0.129* | |
H8B | 0.1067 | 0.7060 | 0.1788 | 0.129* | |
H8C | 0.0972 | 0.7233 | 0.2362 | 0.129* | |
C9 | 0.2917 (6) | 0.5418 (5) | 0.2559 (3) | 0.064 (3) | |
H9A | 0.2776 | 0.5267 | 0.2253 | 0.076* | |
H9B | 0.3438 | 0.5104 | 0.2634 | 0.076* | |
C10 | 0.3117 (7) | 0.6274 (6) | 0.2404 (4) | 0.119 (5) | |
H10A | 0.2629 | 0.6585 | 0.2275 | 0.143* | |
H10B | 0.3182 | 0.6450 | 0.2719 | 0.143* | |
C11 | 0.3895 (6) | 0.6413 (8) | 0.1996 (4) | 0.134 (6) | |
H11A | 0.3918 | 0.6081 | 0.1740 | 0.161* | |
H11B | 0.3849 | 0.6955 | 0.1808 | 0.161* | |
C12 | 0.4655 (7) | 0.6282 (11) | 0.2170 (6) | 0.188 (8) | |
H12A | 0.5129 | 0.6385 | 0.1871 | 0.283* | |
H12B | 0.4718 | 0.5745 | 0.2351 | 0.283* | |
H12C | 0.4654 | 0.6624 | 0.2413 | 0.283* | |
C13 | 0.2421 (5) | 0.5335 (5) | 0.3517 (3) | 0.040 (3) | |
H13A | 0.1919 | 0.5227 | 0.3804 | 0.048* | |
H13B | 0.2510 | 0.5887 | 0.3471 | 0.048* | |
C14 | 0.3181 (6) | 0.4876 (5) | 0.3700 (3) | 0.053 (3) | |
H14A | 0.3702 | 0.5015 | 0.3436 | 0.063* | |
H14B | 0.3122 | 0.4321 | 0.3732 | 0.063* | |
C15 | 0.3263 (5) | 0.5028 (5) | 0.4228 (3) | 0.056 (3) | |
H15A | 0.3298 | 0.5587 | 0.4198 | 0.067* | |
H15B | 0.2748 | 0.4873 | 0.4493 | 0.067* | |
C16 | 0.4036 (6) | 0.4597 (6) | 0.4414 (4) | 0.073 (4) | |
H16A | 0.4063 | 0.4715 | 0.4752 | 0.110* | |
H16B | 0.4550 | 0.4754 | 0.4157 | 0.110* | |
H16C | 0.3998 | 0.4043 | 0.4454 | 0.110* | |
N2 | 0.9857 (4) | 0.8744 (3) | 0.4275 (2) | 0.040 (2) | |
C17 | 0.9985 (5) | 0.9610 (4) | 0.4101 (4) | 0.048 (3) | |
H17A | 0.9536 | 0.9858 | 0.3907 | 0.057* | |
H17B | 0.9909 | 0.9835 | 0.4417 | 0.057* | |
C18 | 1.0836 (5) | 0.9802 (4) | 0.3760 (4) | 0.060 (4) | |
H18A | 1.0898 | 0.9631 | 0.3424 | 0.072* | |
H18B | 1.1296 | 0.9528 | 0.3937 | 0.072* | |
C19 | 1.0914 (5) | 1.0679 (5) | 0.3655 (4) | 0.064 (4) | |
H19A | 1.0464 | 1.0946 | 0.3469 | 0.077* | |
H19B | 1.0820 | 1.0848 | 0.3995 | 0.077* | |
C20 | 1.1765 (6) | 1.0911 (5) | 0.3336 (4) | 0.077 (4) | |
H20A | 1.1778 | 1.1471 | 0.3279 | 0.116* | |
H20B | 1.1859 | 1.0751 | 0.2998 | 0.116* | |
H20C | 1.2213 | 1.0661 | 0.3524 | 0.116* | |
C21 | 1.0566 (5) | 0.8311 (5) | 0.4544 (3) | 0.042 (3) | |
H21A | 1.0452 | 0.7760 | 0.4652 | 0.051* | |
H21B | 1.1110 | 0.8347 | 0.4285 | 0.051* | |
C22 | 1.0676 (5) | 0.8595 (5) | 0.5021 (3) | 0.042 (3) | |
H22A | 1.0130 | 0.8592 | 0.5277 | 0.051* | |
H22B | 1.0849 | 0.9129 | 0.4915 | 0.051* | |
C23 | 1.1357 (5) | 0.8069 (5) | 0.5273 (3) | 0.051 (3) | |
H23A | 1.1189 | 0.7533 | 0.5367 | 0.061* | |
H23B | 1.1903 | 0.8081 | 0.5016 | 0.061* | |
C24 | 1.1479 (6) | 0.8316 (5) | 0.5760 (4) | 0.066 (3) | |
H24A | 1.1927 | 0.7976 | 0.5905 | 0.099* | |
H24B | 1.0946 | 0.8282 | 0.6021 | 0.099* | |
H24C | 1.1641 | 0.8847 | 0.5669 | 0.099* | |
C25 | 0.8996 (5) | 0.8668 (4) | 0.4629 (3) | 0.040 (3) | |
H25A | 0.8580 | 0.9023 | 0.4455 | 0.048* | |
H25B | 0.9015 | 0.8845 | 0.4953 | 0.048* | |
C26 | 0.8658 (5) | 0.7863 (4) | 0.4789 (3) | 0.041 (3) | |
H26A | 0.8516 | 0.7720 | 0.4481 | 0.049* | |
H26B | 0.9104 | 0.7481 | 0.4910 | 0.049* | |
C27 | 0.7871 (5) | 0.7848 (4) | 0.5223 (3) | 0.044 (3) | |
H27A | 0.8024 | 0.7967 | 0.5535 | 0.053* | |
H27B | 0.7441 | 0.8254 | 0.5107 | 0.053* | |
C28 | 0.7496 (6) | 0.7100 (5) | 0.5369 (4) | 0.073 (4) | |
H28A | 0.7005 | 0.7115 | 0.5658 | 0.110* | |
H28B | 0.7921 | 0.6695 | 0.5479 | 0.110* | |
H28C | 0.7314 | 0.6993 | 0.5067 | 0.110* | |
C29 | 0.9904 (5) | 0.8392 (5) | 0.3799 (3) | 0.047 (3) | |
H29A | 1.0486 | 0.8434 | 0.3584 | 0.056* | |
H29B | 0.9819 | 0.7837 | 0.3922 | 0.056* | |
C30 | 0.9278 (6) | 0.8734 (5) | 0.3447 (3) | 0.062 (3) | |
H30A | 0.9443 | 0.9249 | 0.3250 | 0.074* | |
H30B | 0.8703 | 0.8797 | 0.3665 | 0.074* | |
C31 | 0.9258 (6) | 0.8221 (5) | 0.3063 (4) | 0.070 (4) | |
H31A | 0.8954 | 0.8514 | 0.2789 | 0.084* | |
H31B | 0.9849 | 0.8092 | 0.2889 | 0.084* | |
C32 | 0.8839 (7) | 0.7489 (5) | 0.3307 (4) | 0.081 (4) | |
H32A | 0.8868 | 0.7184 | 0.3038 | 0.122* | |
H32B | 0.8243 | 0.7609 | 0.3462 | 0.122* | |
H32C | 0.9133 | 0.7194 | 0.3580 | 0.122* | |
N3 | 0.7577 (4) | 0.4926 (3) | 0.1900 (2) | 0.038 (2) | |
C33 | 0.8323 (5) | 0.4376 (4) | 0.2054 (3) | 0.034 (3) | |
H33A | 0.8151 | 0.3842 | 0.2130 | 0.041* | |
H33B | 0.8803 | 0.4420 | 0.1749 | 0.041* | |
C34 | 0.8634 (6) | 0.4506 (5) | 0.2519 (3) | 0.052 (3) | |
H34A | 0.8152 | 0.4498 | 0.2822 | 0.063* | |
H34B | 0.8862 | 0.5020 | 0.2435 | 0.063* | |
C35 | 0.9330 (6) | 0.3885 (4) | 0.2664 (4) | 0.049 (3) | |
H35A | 0.9777 | 0.3853 | 0.2348 | 0.059* | |
H35B | 0.9595 | 0.4038 | 0.2924 | 0.059* | |
C36 | 0.9004 (7) | 0.3116 (5) | 0.2884 (4) | 0.068 (4) | |
H36A | 0.9473 | 0.2743 | 0.2968 | 0.101* | |
H36B | 0.8751 | 0.2957 | 0.2626 | 0.101* | |
H36C | 0.8572 | 0.3140 | 0.3203 | 0.101* | |
C37 | 0.7788 (5) | 0.5765 (4) | 0.1821 (3) | 0.041 (3) | |
H37A | 0.7309 | 0.6106 | 0.1704 | 0.050* | |
H37B | 0.7833 | 0.5869 | 0.2163 | 0.050* | |
C38 | 0.8598 (5) | 0.5975 (4) | 0.1430 (3) | 0.044 (3) | |
H38A | 0.8564 | 0.5878 | 0.1084 | 0.053* | |
H38B | 0.9088 | 0.5651 | 0.1547 | 0.053* | |
C39 | 0.8727 (5) | 0.6827 (4) | 0.1383 (4) | 0.050 (3) | |
H39A | 0.8250 | 0.7151 | 0.1252 | 0.060* | |
H39B | 0.8734 | 0.6928 | 0.1733 | 0.060* | |
C40 | 0.9558 (6) | 0.7036 (5) | 0.1012 (4) | 0.062 (3) | |
H40A | 0.9627 | 0.7584 | 0.0980 | 0.093* | |
H40B | 0.9553 | 0.6933 | 0.0667 | 0.093* | |
H40C | 1.0032 | 0.6727 | 0.1149 | 0.093* | |
C41 | 0.7422 (5) | 0.4745 (5) | 0.1408 (3) | 0.038 (3) | |
H41A | 0.7347 | 0.4187 | 0.1474 | 0.045* | |
H41B | 0.7942 | 0.4842 | 0.1135 | 0.045* | |
C42 | 0.6664 (5) | 0.5178 (5) | 0.1182 (3) | 0.039 (3) | |
H42A | 0.6127 | 0.5037 | 0.1428 | 0.047* | |
H42B | 0.6699 | 0.5740 | 0.1138 | 0.047* | |
C43 | 0.6665 (5) | 0.4982 (5) | 0.0663 (3) | 0.049 (3) | |
H43A | 0.7209 | 0.5115 | 0.0421 | 0.059* | |
H43B | 0.6630 | 0.4420 | 0.0711 | 0.059* | |
C44 | 0.5945 (6) | 0.5394 (6) | 0.0420 (4) | 0.071 (4) | |
H44A | 0.5967 | 0.5233 | 0.0088 | 0.106* | |
H44B | 0.5993 | 0.5950 | 0.0354 | 0.106* | |
H44C | 0.5404 | 0.5267 | 0.0658 | 0.106* | |
C45 | 0.6798 (5) | 0.4804 (5) | 0.2334 (3) | 0.050 (3) | |
H45A | 0.6923 | 0.4941 | 0.2648 | 0.060* | |
H45B | 0.6331 | 0.5171 | 0.2226 | 0.060* | |
C46 | 0.6483 (6) | 0.4034 (5) | 0.2489 (4) | 0.084 (4) | |
H46A | 0.6910 | 0.3665 | 0.2643 | 0.100* | |
H46B | 0.6394 | 0.3865 | 0.2176 | 0.100* | |
C47 | 0.5613 (7) | 0.4044 (7) | 0.2904 (6) | 0.123 (5) | |
H47A | 0.5732 | 0.4108 | 0.3240 | 0.147* | |
H47B | 0.5240 | 0.4496 | 0.2780 | 0.147* | |
C48 | 0.5177 (13) | 0.3375 (10) | 0.2993 (10) | 0.308 (16) | |
H48A | 0.4642 | 0.3425 | 0.3245 | 0.461* | |
H48B | 0.5530 | 0.2927 | 0.3133 | 0.461* | |
H48C | 0.5056 | 0.3307 | 0.2663 | 0.461* | |
N4 | 0.5386 (4) | 0.2220 (3) | 0.0609 (2) | 0.030 (2) | |
C49 | 0.6085 (5) | 0.1581 (4) | 0.0733 (3) | 0.033 (3) | |
H49A | 0.6608 | 0.1826 | 0.0724 | 0.039* | |
H49B | 0.5900 | 0.1292 | 0.1094 | 0.039* | |
C50 | 0.6299 (5) | 0.1017 (4) | 0.0365 (3) | 0.044 (3) | |
H50A | 0.6542 | 0.1285 | 0.0007 | 0.053* | |
H50B | 0.5779 | 0.0784 | 0.0354 | 0.053* | |
C51 | 0.6949 (6) | 0.0389 (5) | 0.0570 (4) | 0.054 (3) | |
H51A | 0.7463 | 0.0630 | 0.0581 | 0.065* | |
H51B | 0.6703 | 0.0135 | 0.0932 | 0.065* | |
C52 | 0.7195 (7) | −0.0204 (5) | 0.0233 (4) | 0.086 (4) | |
H52A | 0.7598 | −0.0599 | 0.0380 | 0.129* | |
H52B | 0.7462 | 0.0042 | −0.0122 | 0.129* | |
H52C | 0.6687 | −0.0442 | 0.0219 | 0.129* | |
C53 | 0.5632 (5) | 0.2688 (5) | 0.0060 (3) | 0.042 (3) | |
H53A | 0.5663 | 0.2347 | −0.0192 | 0.051* | |
H53B | 0.5171 | 0.3095 | 0.0001 | 0.051* | |
C54 | 0.6459 (5) | 0.3066 (5) | −0.0068 (3) | 0.046 (3) | |
H54A | 0.6927 | 0.2679 | 0.0011 | 0.056* | |
H54B | 0.6419 | 0.3464 | 0.0145 | 0.056* | |
C55 | 0.6633 (6) | 0.3433 (6) | −0.0648 (3) | 0.062 (3) | |
H55A | 0.6625 | 0.3035 | −0.0853 | 0.075* | |
H55B | 0.6169 | 0.3832 | −0.0716 | 0.075* | |
C56 | 0.7462 (6) | 0.3793 (6) | −0.0835 (4) | 0.077 (4) | |
H56A | 0.7535 | 0.4008 | −0.1211 | 0.115* | |
H56B | 0.7927 | 0.3402 | −0.0772 | 0.115* | |
H56C | 0.7467 | 0.4205 | −0.0645 | 0.115* | |
C57 | 0.4557 (4) | 0.1888 (4) | 0.0646 (3) | 0.036 (3) | |
H57A | 0.4128 | 0.2322 | 0.0577 | 0.043* | |
H57B | 0.4634 | 0.1597 | 0.0360 | 0.043* | |
C58 | 0.4190 (5) | 0.1363 (5) | 0.1154 (3) | 0.053 (3) | |
H58A | 0.4116 | 0.1638 | 0.1447 | 0.064* | |
H58B | 0.4592 | 0.0906 | 0.1219 | 0.064* | |
C59 | 0.3338 (5) | 0.1103 (6) | 0.1134 (4) | 0.074 (4) | |
H59A | 0.2938 | 0.1561 | 0.1067 | 0.088* | |
H59B | 0.3414 | 0.0829 | 0.0840 | 0.088* | |
C60 | 0.2973 (7) | 0.0598 (6) | 0.1618 (4) | 0.104 (5) | |
H60A | 0.2434 | 0.0434 | 0.1584 | 0.156* | |
H60B | 0.2870 | 0.0875 | 0.1908 | 0.156* | |
H60C | 0.3368 | 0.0145 | 0.1688 | 0.156* | |
C61 | 0.5317 (5) | 0.2712 (4) | 0.1023 (3) | 0.040 (3) | |
H61A | 0.5212 | 0.2371 | 0.1373 | 0.048* | |
H61B | 0.5872 | 0.2927 | 0.0976 | 0.048* | |
C62 | 0.4643 (6) | 0.3362 (5) | 0.1020 (3) | 0.055 (3) | |
H62A | 0.4074 | 0.3162 | 0.1094 | 0.066* | |
H62B | 0.4726 | 0.3711 | 0.0673 | 0.066* | |
C63 | 0.4716 (6) | 0.3794 (5) | 0.1447 (4) | 0.072 (4) | |
H63A | 0.4683 | 0.3425 | 0.1785 | 0.086* | |
H63B | 0.5278 | 0.4011 | 0.1357 | 0.086* | |
C64 | 0.4058 (8) | 0.4408 (7) | 0.1506 (5) | 0.134 (7) | |
H64A | 0.4137 | 0.4672 | 0.1775 | 0.201* | |
H64B | 0.3501 | 0.4194 | 0.1609 | 0.201* | |
H64C | 0.4087 | 0.4775 | 0.1172 | 0.201* | |
N5 | 0.0225 (4) | 0.1350 (3) | 0.0887 (3) | 0.040 (2) | |
C65 | 0.0126 (5) | 0.0487 (4) | 0.1089 (4) | 0.048 (3) | |
H65A | 0.0128 | 0.0244 | 0.0788 | 0.058* | |
H65B | 0.0623 | 0.0255 | 0.1243 | 0.058* | |
C66 | −0.0682 (6) | 0.0302 (5) | 0.1498 (4) | 0.078 (4) | |
H66A | −0.1177 | 0.0605 | 0.1375 | 0.094* | |
H66B | −0.0639 | 0.0445 | 0.1829 | 0.094* | |
C67 | −0.0812 (7) | −0.0557 (5) | 0.1598 (4) | 0.082 (4) | |
H67A | −0.0264 | −0.0862 | 0.1621 | 0.098* | |
H67B | −0.1214 | −0.0704 | 0.1935 | 0.098* | |
C68 | −0.1146 (8) | −0.0724 (6) | 0.1177 (5) | 0.125 (6) | |
H68A | −0.1219 | −0.1276 | 0.1240 | 0.188* | |
H68B | −0.0749 | −0.0576 | 0.0844 | 0.188* | |
H68C | −0.1697 | −0.0433 | 0.1161 | 0.188* | |
C69 | 0.1101 (5) | 0.1418 (4) | 0.0526 (3) | 0.041 (3) | |
H69A | 0.1523 | 0.1094 | 0.0712 | 0.049* | |
H69B | 0.1094 | 0.1203 | 0.0215 | 0.049* | |
C70 | 0.1401 (5) | 0.2213 (4) | 0.0339 (3) | 0.041 (3) | |
H70A | 0.1545 | 0.2392 | 0.0633 | 0.049* | |
H70B | 0.0940 | 0.2571 | 0.0214 | 0.049* | |
C71 | 0.2175 (5) | 0.2216 (5) | −0.0101 (4) | 0.055 (3) | |
H71A | 0.2616 | 0.1822 | 0.0015 | 0.066* | |
H71B | 0.2017 | 0.2083 | −0.0407 | 0.066* | |
C72 | 0.2531 (6) | 0.2995 (5) | −0.0259 (4) | 0.071 (4) | |
H72A | 0.3025 | 0.2987 | −0.0547 | 0.106* | |
H72B | 0.2706 | 0.3120 | 0.0041 | 0.106* | |
H72C | 0.2095 | 0.3385 | −0.0373 | 0.106* | |
C73 | 0.0152 (6) | 0.1756 (5) | 0.1337 (3) | 0.054 (3) | |
H73A | −0.0428 | 0.1708 | 0.1553 | 0.064* | |
H73B | 0.0217 | 0.2310 | 0.1192 | 0.064* | |
C74 | 0.0799 (6) | 0.1460 (5) | 0.1696 (3) | 0.064 (4) | |
H74A | 0.0692 | 0.0925 | 0.1879 | 0.076* | |
H74B | 0.1381 | 0.1455 | 0.1479 | 0.076* | |
C75 | 0.0740 (7) | 0.1957 (5) | 0.2097 (4) | 0.075 (4) | |
H75A | 0.0143 | 0.2012 | 0.2286 | 0.089* | |
H75B | 0.1090 | 0.1703 | 0.2356 | 0.089* | |
C76 | 0.1029 (8) | 0.2711 (6) | 0.1855 (5) | 0.094 (5) | |
H76A | 0.0978 | 0.3019 | 0.2124 | 0.141* | |
H76B | 0.0679 | 0.2966 | 0.1601 | 0.141* | |
H76C | 0.1624 | 0.2659 | 0.1675 | 0.141* | |
C77 | −0.0481 (5) | 0.1714 (5) | 0.0601 (3) | 0.041 (3) | |
H77A | −0.1029 | 0.1665 | 0.0855 | 0.050* | |
H77B | −0.0402 | 0.2271 | 0.0481 | 0.050* | |
C78 | −0.0554 (5) | 0.1391 (5) | 0.0135 (3) | 0.047 (3) | |
H78A | −0.0669 | 0.0841 | 0.0247 | 0.056* | |
H78B | −0.0013 | 0.1431 | −0.0127 | 0.056* | |
C79 | −0.1278 (6) | 0.1847 (5) | −0.0108 (3) | 0.054 (3) | |
H79A | −0.1805 | 0.1832 | 0.0165 | 0.065* | |
H79B | −0.1143 | 0.2391 | −0.0230 | 0.065* | |
C80 | −0.1435 (6) | 0.1545 (6) | −0.0560 (4) | 0.065 (4) | |
H80A | −0.1906 | 0.1857 | −0.0698 | 0.098* | |
H80B | −0.1580 | 0.1009 | −0.0440 | 0.098* | |
H80C | −0.0921 | 0.1572 | −0.0836 | 0.098* | |
N6 | 0.4709 (4) | 0.7650 (4) | 0.4390 (2) | 0.043 (2) | |
C81 | 0.5503 (5) | 0.8023 (5) | 0.4425 (3) | 0.045 (3) | |
H81A | 0.5353 | 0.8292 | 0.4724 | 0.054* | |
H81B | 0.5949 | 0.7609 | 0.4500 | 0.054* | |
C82 | 0.5872 (5) | 0.8594 (5) | 0.3936 (3) | 0.057 (3) | |
H82A | 0.5442 | 0.9021 | 0.3852 | 0.068* | |
H82B | 0.6055 | 0.8335 | 0.3632 | 0.068* | |
C83 | 0.6636 (6) | 0.8902 (6) | 0.4057 (4) | 0.085 (4) | |
H83A | 0.6445 | 0.9141 | 0.4370 | 0.102* | |
H83B | 0.7059 | 0.8469 | 0.4139 | 0.102* | |
C84 | 0.7038 (7) | 0.9479 (7) | 0.3611 (5) | 0.126 (6) | |
H84A | 0.7523 | 0.9663 | 0.3700 | 0.189* | |
H84B | 0.6623 | 0.9913 | 0.3534 | 0.189* | |
H84C | 0.7235 | 0.9241 | 0.3303 | 0.189* | |
C85 | 0.4005 (5) | 0.8281 (4) | 0.4265 (3) | 0.042 (3) | |
H85A | 0.4200 | 0.8583 | 0.3909 | 0.050* | |
H85B | 0.3496 | 0.8029 | 0.4258 | 0.050* | |
C86 | 0.3741 (6) | 0.8837 (5) | 0.4642 (3) | 0.050 (3) | |
H86A | 0.4239 | 0.9095 | 0.4662 | 0.060* | |
H86B | 0.3500 | 0.8556 | 0.4998 | 0.060* | |
C87 | 0.3074 (6) | 0.9428 (5) | 0.4432 (4) | 0.058 (3) | |
H87A | 0.3320 | 0.9689 | 0.4072 | 0.070* | |
H87B | 0.2584 | 0.9159 | 0.4414 | 0.070* | |
C88 | 0.2768 (7) | 1.0024 (5) | 0.4769 (4) | 0.086 (4) | |
H88A | 0.2341 | 1.0389 | 0.4620 | 0.129* | |
H88B | 0.3249 | 1.0301 | 0.4781 | 0.129* | |
H88C | 0.2515 | 0.9770 | 0.5124 | 0.129* | |
C89 | 0.4446 (6) | 0.7150 (5) | 0.4930 (3) | 0.064 (4) | |
H89A | 0.4938 | 0.6795 | 0.5013 | 0.077* | |
H89B | 0.4296 | 0.7486 | 0.5193 | 0.077* | |
C90 | 0.3695 (7) | 0.6678 (7) | 0.4980 (4) | 0.103 (4) | |
H90A | 0.3177 | 0.7030 | 0.4957 | 0.123* | |
H90B | 0.3804 | 0.6404 | 0.4683 | 0.123* | |
C91 | 0.3543 (8) | 0.6104 (9) | 0.5483 (5) | 0.198 (9) | |
H91A | 0.3469 | 0.5599 | 0.5409 | 0.238* | |
H91B | 0.4048 | 0.6044 | 0.5645 | 0.238* | |
C92 | 0.2860 (11) | 0.6311 (11) | 0.5820 (5) | 0.221 (11) | |
H92A | 0.2908 | 0.6052 | 0.6177 | 0.332* | |
H92B | 0.2349 | 0.6162 | 0.5737 | 0.332* | |
H92C | 0.2820 | 0.6870 | 0.5795 | 0.332* | |
C93 | 0.4892 (6) | 0.7204 (5) | 0.3947 (3) | 0.059 (3) | |
H93A | 0.4359 | 0.6995 | 0.3934 | 0.070* | |
H93B | 0.5063 | 0.7568 | 0.3612 | 0.070* | |
C94 | 0.5574 (7) | 0.6549 (6) | 0.3986 (4) | 0.089 (4) | |
H94A | 0.5426 | 0.6191 | 0.4326 | 0.107* | |
H94B | 0.6123 | 0.6754 | 0.3970 | 0.107* | |
C95 | 0.5663 (9) | 0.6106 (6) | 0.3532 (4) | 0.111 (6) | |
H95A | 0.5987 | 0.5602 | 0.3609 | 0.133* | |
H95B | 0.5095 | 0.6016 | 0.3484 | 0.133* | |
C96 | 0.6138 (11) | 0.6615 (8) | 0.3036 (5) | 0.183 (9) | |
H96A | 0.6192 | 0.6368 | 0.2736 | 0.275* | |
H96B | 0.6706 | 0.6685 | 0.3085 | 0.275* | |
H96C | 0.5820 | 0.7118 | 0.2973 | 0.275* | |
P1 | 0.06399 (15) | 0.59852 (12) | 0.45673 (9) | 0.0325 (7) | |
O1 | 0.0795 (4) | 0.5160 (3) | 0.4511 (2) | 0.056 (2) | |
O2 | 0.1356 (3) | 0.6232 (3) | 0.4785 (2) | 0.0506 (19) | |
H02 | 0.1703 | 0.6470 | 0.4537 | 0.076* | |
O3 | 0.0532 (3) | 0.6557 (3) | 0.40727 (19) | 0.0410 (17) | |
O4 | −0.0176 (3) | 0.6052 (3) | 0.4990 (2) | 0.0374 (17) | |
H04 | −0.0360 | 0.5615 | 0.5111 | 0.056* | |
P2 | 0.24443 (15) | 0.75041 (13) | 0.36257 (9) | 0.0325 (7) | |
O5 | 0.2377 (4) | 0.7147 (4) | 0.4191 (2) | 0.067 (2) | |
O6 | 0.3274 (3) | 0.7278 (3) | 0.3285 (2) | 0.053 (2) | |
O7 | 0.2323 (3) | 0.8388 (3) | 0.3564 (2) | 0.0428 (18) | |
H07 | 0.2718 | 0.8588 | 0.3332 | 0.064* | |
O8 | 0.1709 (3) | 0.7255 (3) | 0.34183 (19) | 0.0330 (16) | |
H08 | 0.1392 | 0.6984 | 0.3666 | 0.049* | |
P3 | 0.93061 (14) | 0.40520 (12) | 0.04497 (9) | 0.0291 (7) | |
O9 | 0.8619 (3) | 0.3734 (3) | 0.0238 (2) | 0.0433 (18) | |
H09 | 0.8287 | 0.3485 | 0.0490 | 0.065* | |
O10 | 0.9100 (4) | 0.4894 (3) | 0.0453 (2) | 0.050 (2) | |
O11 | 1.0150 (3) | 0.3935 (3) | 0.0057 (2) | 0.0375 (18) | |
H011 | 1.0314 | 0.4365 | −0.0108 | 0.056* | |
O12 | 0.9367 (3) | 0.3566 (3) | 0.09825 (19) | 0.0403 (17) | |
P4 | 0.75276 (15) | 0.24823 (13) | 0.14253 (9) | 0.0308 (7) | |
O13 | 0.7467 (3) | 0.2976 (3) | 0.0897 (2) | 0.0483 (19) | |
O14 | 0.8252 (3) | 0.2760 (3) | 0.16352 (19) | 0.0330 (16) | |
H014 | 0.8578 | 0.3017 | 0.1384 | 0.049* | |
O15 | 0.7681 (3) | 0.1635 (3) | 0.1424 (2) | 0.0415 (18) | |
O16 | 0.6712 (3) | 0.2629 (3) | 0.1831 (2) | 0.0440 (19) | |
H016 | 0.6525 | 0.2207 | 0.1995 | 0.066* | |
P5 | 0.59158 (17) | 0.07376 (16) | 0.22572 (11) | 0.0525 (9) | |
O17 | 0.6890 (3) | 0.0588 (3) | 0.2097 (2) | 0.054 (2) | |
H017 | 0.7088 | 0.0964 | 0.1871 | 0.081* | |
O18 | 0.5698 (4) | 0.1577 (4) | 0.2186 (3) | 0.098 (3) | |
O19 | 0.5631 (4) | 0.0285 (4) | 0.2811 (2) | 0.068 (2) | |
O20 | 0.5492 (5) | 0.0447 (5) | 0.1889 (2) | 0.138 (3) | |
H020 | 0.5070 | 0.0209 | 0.2063 | 0.207* | |
P6 | 0.42634 (18) | 0.89779 (19) | 0.26767 (12) | 0.0750 (11) | |
O21 | 0.4540 (4) | 0.9405 (4) | 0.2131 (2) | 0.069 (2) | |
O22 | 0.4973 (5) | 0.8959 (5) | 0.2965 (3) | 0.122 (3) | |
H022 | 0.5366 | 0.9214 | 0.2769 | 0.183* | |
O23 | 0.4301 (5) | 0.8113 (4) | 0.2672 (4) | 0.160 (5) | |
H023 | 0.3826 | 0.7944 | 0.2819 | 0.240* | |
O24 | 0.3378 (4) | 0.9237 (3) | 0.2920 (2) | 0.076 (3) | |
C97 | 0.5136 (8) | 0.1379 (5) | 0.8849 (3) | 0.146 (7) | |
H97A | 0.4754 | 0.1221 | 0.8654 | 0.175* | |
H97B | 0.5670 | 0.1520 | 0.8598 | 0.175* | |
Cl1 | 0.5364 (3) | 0.0613 (3) | 0.93200 (15) | 0.1443 (17) | |
Cl2 | 0.4660 (3) | 0.2184 (3) | 0.90948 (16) | 0.1478 (17) | |
C98 | 0.8684 (5) | 0.5455 (5) | 0.4221 (3) | 0.056 (3) | |
H98A | 0.8691 | 0.5007 | 0.4513 | 0.067* | |
H98B | 0.9109 | 0.5800 | 0.4236 | 0.067* | |
Cl3 | 0.76786 (19) | 0.59430 (17) | 0.42954 (13) | 0.0851 (11) | |
Cl4 | 0.8960 (2) | 0.51379 (18) | 0.36262 (11) | 0.0825 (11) | |
C99 | 0.3317 (8) | 0.1445 (7) | 0.7840 (4) | 0.144 (6) | |
H99A | 0.3876 | 0.1538 | 0.7605 | 0.172* | |
H99B | 0.3262 | 0.0883 | 0.7930 | 0.172* | |
Cl5 | 0.2520 (3) | 0.1891 (2) | 0.75182 (17) | 0.1362 (16) | |
Cl6 | 0.3268 (3) | 0.1794 (2) | 0.84170 (17) | 0.1353 (15) | |
C100 | 0.4927 (8) | 0.1275 (5) | 0.3888 (4) | 0.090 (4) | |
H10C | 0.4356 | 0.1221 | 0.3828 | 0.108* | |
H10D | 0.5346 | 0.1236 | 0.3561 | 0.108* | |
Cl7 | 0.5158 (3) | 0.0571 (2) | 0.43734 (15) | 0.1303 (16) | |
Cl8 | 0.4948 (4) | 0.2166 (3) | 0.40473 (18) | 0.182 (2) | |
C101 | 0.2125 (6) | 0.8662 (5) | 0.2282 (3) | 0.060 (3) | |
H10E | 0.2575 | 0.8915 | 0.2367 | 0.072* | |
H10F | 0.2032 | 0.8174 | 0.2540 | 0.072* | |
Cl9 | 0.2456 (3) | 0.8463 (2) | 0.16603 (14) | 0.1248 (15) | |
Cl10 | 0.1168 (2) | 0.9271 (2) | 0.23329 (15) | 0.1117 (14) | |
C102 | 0.1250 (5) | 0.4538 (6) | 0.0830 (3) | 0.059 (3) | |
H10P | 0.0871 | 0.4154 | 0.0810 | 0.071* | |
H10Q | 0.1246 | 0.4963 | 0.0523 | 0.071* | |
Cl11 | 0.2285 (2) | 0.41080 (19) | 0.08117 (14) | 0.0958 (12) | |
Cl12 | 0.08617 (17) | 0.49015 (15) | 0.14085 (10) | 0.0626 (9) | |
C103 | 0.2175 (6) | 0.8624 (6) | 0.7237 (3) | 0.077 (4) | |
H10G | 0.2041 | 0.8212 | 0.7550 | 0.093* | |
H10H | 0.2475 | 0.9012 | 0.7329 | 0.093* | |
Cl13 | 0.1239 (2) | 0.90537 (18) | 0.70507 (12) | 0.0871 (11) | |
Cl14 | 0.2840 (2) | 0.8231 (2) | 0.67235 (15) | 0.1053 (13) | |
C104 | 0.3699 (7) | 0.1944 (8) | 0.2630 (4) | 0.138 (7) | |
H10I | 0.4290 | 0.1987 | 0.2430 | 0.165* | |
H10J | 0.3585 | 0.1393 | 0.2722 | 0.165* | |
Cl15 | 0.2993 (3) | 0.2458 (3) | 0.22479 (18) | 0.1446 (18) | |
Cl16 | 0.3571 (4) | 0.2316 (5) | 0.3206 (3) | 0.288 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.058 (5) | 0.064 (5) | 0.020 (4) | −0.038 (4) | 0.019 (4) | −0.017 (4) |
C1 | 0.051 (6) | 0.039 (5) | 0.026 (5) | −0.018 (5) | 0.017 (5) | −0.010 (4) |
C2 | 0.030 (5) | 0.044 (5) | 0.034 (5) | −0.019 (5) | −0.002 (5) | −0.006 (4) |
C3 | 0.051 (7) | 0.026 (5) | 0.067 (7) | −0.012 (5) | −0.002 (6) | −0.011 (5) |
C4 | 0.065 (7) | 0.052 (6) | 0.057 (7) | −0.030 (6) | −0.015 (6) | −0.002 (5) |
C5 | 0.057 (7) | 0.035 (5) | 0.038 (6) | −0.009 (5) | 0.002 (5) | −0.017 (5) |
C6 | 0.095 (8) | 0.066 (7) | 0.040 (6) | −0.052 (7) | −0.007 (6) | −0.003 (6) |
C7 | 0.085 (9) | 0.086 (8) | 0.056 (7) | −0.038 (7) | −0.022 (7) | 0.003 (6) |
C8 | 0.148 (12) | 0.070 (8) | 0.043 (7) | −0.036 (8) | −0.026 (7) | 0.003 (6) |
C9 | 0.059 (7) | 0.083 (8) | 0.043 (6) | −0.046 (6) | 0.021 (6) | −0.008 (6) |
C10 | 0.168 (11) | 0.147 (10) | 0.050 (7) | −0.126 (9) | 0.034 (8) | −0.035 (7) |
C11 | 0.138 (12) | 0.190 (13) | 0.073 (9) | −0.114 (11) | 0.051 (9) | −0.043 (9) |
C12 | 0.045 (10) | 0.33 (2) | 0.230 (18) | 0.018 (13) | −0.018 (11) | −0.174 (17) |
C13 | 0.043 (6) | 0.042 (6) | 0.032 (5) | −0.013 (5) | 0.001 (5) | −0.004 (5) |
C14 | 0.068 (7) | 0.054 (6) | 0.035 (6) | −0.028 (6) | 0.008 (6) | −0.013 (5) |
C15 | 0.044 (6) | 0.056 (7) | 0.064 (7) | −0.010 (6) | −0.017 (6) | 0.005 (6) |
C16 | 0.059 (8) | 0.084 (8) | 0.071 (8) | 0.020 (7) | −0.021 (7) | −0.011 (7) |
N2 | 0.041 (5) | 0.031 (4) | 0.040 (5) | 0.006 (4) | −0.002 (4) | −0.002 (4) |
C17 | 0.032 (6) | 0.019 (5) | 0.082 (7) | 0.002 (5) | −0.006 (6) | 0.003 (5) |
C18 | 0.052 (7) | 0.032 (6) | 0.076 (8) | 0.003 (5) | 0.003 (6) | 0.013 (5) |
C19 | 0.040 (7) | 0.044 (6) | 0.092 (8) | −0.001 (6) | 0.009 (6) | 0.000 (6) |
C20 | 0.067 (8) | 0.048 (7) | 0.093 (9) | −0.013 (6) | 0.008 (7) | 0.016 (6) |
C21 | 0.029 (6) | 0.047 (6) | 0.045 (6) | 0.017 (5) | −0.016 (5) | 0.003 (5) |
C22 | 0.049 (6) | 0.034 (5) | 0.038 (6) | −0.001 (5) | −0.003 (5) | 0.001 (5) |
C23 | 0.035 (6) | 0.053 (6) | 0.063 (7) | −0.006 (5) | −0.019 (5) | 0.001 (6) |
C24 | 0.075 (8) | 0.060 (7) | 0.074 (8) | −0.024 (6) | −0.029 (7) | −0.009 (6) |
C25 | 0.028 (5) | 0.037 (5) | 0.047 (6) | 0.005 (5) | −0.007 (5) | 0.000 (5) |
C26 | 0.031 (6) | 0.043 (6) | 0.042 (6) | 0.001 (5) | −0.007 (5) | 0.004 (5) |
C27 | 0.046 (6) | 0.035 (5) | 0.038 (6) | −0.014 (5) | 0.008 (5) | 0.009 (5) |
C28 | 0.067 (8) | 0.067 (8) | 0.077 (8) | −0.018 (7) | −0.007 (7) | 0.003 (7) |
C29 | 0.032 (6) | 0.051 (6) | 0.047 (6) | −0.005 (5) | −0.008 (5) | 0.014 (5) |
C30 | 0.051 (7) | 0.061 (7) | 0.065 (7) | 0.006 (6) | −0.032 (6) | 0.023 (6) |
C31 | 0.058 (7) | 0.072 (8) | 0.078 (8) | −0.009 (6) | −0.041 (6) | 0.016 (7) |
C32 | 0.090 (9) | 0.058 (8) | 0.101 (9) | −0.007 (7) | −0.043 (8) | −0.001 (7) |
N3 | 0.037 (5) | 0.040 (5) | 0.032 (4) | 0.002 (4) | 0.000 (4) | −0.007 (4) |
C33 | 0.036 (6) | 0.040 (5) | 0.026 (5) | −0.004 (5) | 0.004 (5) | −0.014 (4) |
C34 | 0.068 (7) | 0.048 (6) | 0.042 (6) | −0.011 (6) | −0.011 (6) | −0.008 (5) |
C35 | 0.055 (7) | 0.047 (6) | 0.046 (6) | 0.001 (6) | −0.013 (5) | −0.012 (5) |
C36 | 0.071 (8) | 0.063 (7) | 0.064 (7) | −0.008 (7) | −0.012 (7) | −0.003 (6) |
C37 | 0.045 (6) | 0.025 (5) | 0.047 (6) | −0.006 (5) | −0.003 (5) | 0.001 (5) |
C38 | 0.058 (7) | 0.036 (5) | 0.035 (6) | −0.010 (5) | −0.001 (5) | −0.005 (5) |
C39 | 0.048 (7) | 0.031 (5) | 0.065 (7) | −0.009 (5) | 0.003 (6) | −0.006 (5) |
C40 | 0.074 (8) | 0.051 (6) | 0.061 (7) | −0.039 (6) | −0.008 (6) | 0.000 (5) |
C41 | 0.035 (6) | 0.046 (6) | 0.034 (5) | 0.002 (5) | −0.010 (5) | −0.013 (5) |
C42 | 0.027 (5) | 0.047 (6) | 0.040 (6) | 0.000 (5) | −0.009 (5) | −0.004 (5) |
C43 | 0.037 (6) | 0.047 (6) | 0.063 (7) | 0.004 (5) | −0.025 (5) | 0.002 (5) |
C44 | 0.046 (7) | 0.066 (7) | 0.087 (8) | −0.014 (6) | −0.031 (6) | 0.036 (6) |
C45 | 0.031 (6) | 0.046 (6) | 0.056 (7) | −0.012 (5) | 0.021 (5) | 0.003 (5) |
C46 | 0.088 (7) | 0.077 (6) | 0.074 (7) | −0.033 (6) | 0.022 (6) | −0.015 (6) |
C47 | 0.085 (8) | 0.100 (8) | 0.163 (9) | −0.026 (7) | −0.017 (7) | 0.020 (7) |
C48 | 0.34 (3) | 0.18 (2) | 0.43 (4) | −0.06 (2) | −0.15 (3) | 0.00 (2) |
N4 | 0.019 (4) | 0.038 (4) | 0.029 (4) | −0.004 (4) | −0.012 (3) | 0.008 (3) |
C49 | 0.025 (5) | 0.040 (5) | 0.031 (5) | −0.005 (5) | −0.009 (4) | 0.004 (4) |
C50 | 0.039 (6) | 0.047 (6) | 0.044 (6) | −0.001 (5) | 0.002 (5) | −0.015 (5) |
C51 | 0.054 (7) | 0.038 (6) | 0.064 (7) | 0.010 (6) | −0.007 (6) | −0.007 (5) |
C52 | 0.083 (9) | 0.067 (8) | 0.097 (9) | 0.022 (7) | 0.004 (8) | −0.029 (7) |
C53 | 0.034 (6) | 0.050 (6) | 0.034 (5) | 0.002 (5) | −0.007 (5) | 0.009 (5) |
C54 | 0.037 (6) | 0.064 (7) | 0.028 (5) | −0.011 (5) | −0.001 (5) | 0.009 (5) |
C55 | 0.059 (7) | 0.058 (7) | 0.064 (7) | −0.010 (6) | −0.025 (6) | 0.014 (6) |
C56 | 0.075 (8) | 0.079 (8) | 0.070 (8) | −0.042 (7) | −0.012 (7) | 0.016 (7) |
C57 | 0.025 (5) | 0.036 (5) | 0.051 (6) | −0.001 (4) | −0.021 (5) | −0.006 (5) |
C58 | 0.038 (6) | 0.062 (7) | 0.053 (6) | −0.011 (6) | −0.016 (5) | 0.016 (5) |
C59 | 0.025 (6) | 0.067 (7) | 0.113 (9) | −0.013 (6) | −0.022 (6) | 0.031 (7) |
C60 | 0.062 (8) | 0.073 (8) | 0.145 (11) | −0.019 (7) | −0.023 (8) | 0.057 (8) |
C61 | 0.022 (5) | 0.051 (6) | 0.043 (6) | 0.003 (5) | −0.012 (5) | −0.001 (5) |
C62 | 0.061 (7) | 0.050 (6) | 0.047 (6) | 0.018 (6) | −0.006 (6) | −0.013 (5) |
C63 | 0.046 (7) | 0.049 (7) | 0.126 (10) | 0.012 (6) | −0.020 (7) | −0.036 (7) |
C64 | 0.154 (15) | 0.107 (11) | 0.120 (12) | −0.036 (11) | 0.024 (12) | −0.015 (10) |
N5 | 0.028 (4) | 0.028 (4) | 0.056 (5) | 0.001 (4) | −0.003 (4) | 0.002 (4) |
C65 | 0.029 (6) | 0.030 (5) | 0.074 (7) | 0.000 (5) | 0.002 (6) | 0.000 (5) |
C66 | 0.074 (8) | 0.045 (7) | 0.091 (9) | −0.029 (6) | 0.021 (7) | 0.013 (6) |
C67 | 0.050 (7) | 0.061 (8) | 0.127 (11) | −0.013 (6) | −0.016 (8) | 0.000 (8) |
C68 | 0.111 (12) | 0.052 (8) | 0.212 (17) | −0.017 (8) | −0.040 (12) | −0.013 (10) |
C69 | 0.038 (6) | 0.031 (5) | 0.047 (6) | 0.006 (5) | −0.007 (5) | −0.001 (5) |
C70 | 0.034 (6) | 0.032 (5) | 0.053 (6) | −0.003 (5) | 0.001 (5) | −0.008 (5) |
C71 | 0.044 (7) | 0.047 (6) | 0.060 (7) | 0.005 (6) | −0.002 (6) | 0.005 (5) |
C72 | 0.060 (7) | 0.040 (6) | 0.093 (8) | −0.019 (6) | 0.002 (7) | 0.016 (6) |
C73 | 0.049 (7) | 0.052 (6) | 0.054 (7) | 0.014 (6) | −0.004 (6) | −0.011 (6) |
C74 | 0.066 (8) | 0.057 (7) | 0.064 (7) | 0.017 (6) | −0.028 (6) | 0.001 (6) |
C75 | 0.082 (9) | 0.076 (8) | 0.060 (7) | 0.001 (7) | −0.016 (7) | −0.001 (7) |
C76 | 0.125 (11) | 0.072 (8) | 0.101 (10) | 0.012 (8) | −0.058 (9) | −0.025 (7) |
C77 | 0.029 (6) | 0.039 (6) | 0.052 (6) | 0.000 (5) | −0.007 (5) | −0.003 (5) |
C78 | 0.030 (6) | 0.046 (6) | 0.065 (7) | −0.003 (5) | −0.009 (5) | −0.013 (5) |
C79 | 0.053 (7) | 0.064 (7) | 0.046 (6) | −0.014 (6) | −0.008 (6) | −0.011 (5) |
C80 | 0.058 (7) | 0.069 (7) | 0.073 (8) | −0.015 (6) | −0.002 (6) | −0.027 (6) |
N6 | 0.031 (5) | 0.054 (5) | 0.040 (5) | −0.007 (4) | −0.009 (4) | 0.006 (4) |
C81 | 0.032 (6) | 0.059 (6) | 0.046 (6) | −0.007 (5) | −0.012 (5) | −0.007 (5) |
C82 | 0.035 (6) | 0.060 (7) | 0.063 (7) | −0.013 (6) | −0.001 (6) | 0.010 (6) |
C83 | 0.031 (6) | 0.066 (7) | 0.129 (10) | −0.014 (6) | −0.019 (7) | 0.053 (7) |
C84 | 0.061 (8) | 0.084 (10) | 0.238 (17) | 0.007 (8) | −0.085 (10) | 0.008 (11) |
C85 | 0.033 (6) | 0.042 (6) | 0.052 (6) | 0.006 (5) | −0.019 (5) | −0.004 (5) |
C86 | 0.045 (6) | 0.049 (6) | 0.058 (6) | 0.010 (5) | −0.023 (5) | −0.009 (5) |
C87 | 0.038 (6) | 0.064 (7) | 0.076 (8) | −0.007 (6) | −0.011 (6) | −0.022 (6) |
C88 | 0.091 (10) | 0.061 (7) | 0.100 (9) | 0.006 (7) | 0.016 (8) | −0.046 (7) |
C89 | 0.050 (7) | 0.084 (8) | 0.044 (6) | −0.015 (6) | −0.017 (6) | 0.034 (6) |
C90 | 0.081 (7) | 0.117 (8) | 0.096 (7) | −0.031 (6) | −0.032 (6) | 0.038 (6) |
C91 | 0.087 (11) | 0.255 (19) | 0.174 (14) | −0.046 (12) | −0.041 (11) | 0.161 (14) |
C92 | 0.23 (2) | 0.29 (2) | 0.070 (11) | 0.176 (18) | 0.003 (13) | −0.020 (13) |
C93 | 0.085 (8) | 0.055 (6) | 0.057 (6) | −0.001 (6) | −0.034 (6) | −0.037 (5) |
C94 | 0.110 (10) | 0.082 (8) | 0.074 (8) | 0.059 (8) | −0.040 (8) | −0.024 (7) |
C95 | 0.152 (14) | 0.065 (9) | 0.108 (11) | 0.011 (9) | −0.030 (11) | −0.005 (8) |
C96 | 0.26 (2) | 0.090 (11) | 0.144 (14) | 0.051 (13) | 0.049 (15) | −0.040 (11) |
P1 | 0.0351 (15) | 0.0244 (13) | 0.0355 (14) | −0.0097 (12) | −0.0041 (13) | 0.0005 (11) |
O1 | 0.066 (5) | 0.029 (4) | 0.054 (4) | −0.011 (3) | 0.033 (4) | −0.006 (3) |
O2 | 0.048 (4) | 0.058 (4) | 0.042 (4) | −0.023 (3) | −0.022 (3) | 0.020 (3) |
O3 | 0.050 (4) | 0.038 (3) | 0.036 (3) | −0.021 (3) | −0.022 (3) | 0.014 (3) |
O4 | 0.040 (4) | 0.015 (3) | 0.050 (4) | −0.007 (3) | 0.003 (3) | −0.002 (3) |
P2 | 0.0265 (14) | 0.0259 (13) | 0.0440 (15) | −0.0068 (11) | −0.0068 (12) | −0.0025 (12) |
O5 | 0.073 (5) | 0.082 (5) | 0.054 (4) | −0.051 (4) | −0.040 (4) | 0.021 (4) |
O6 | 0.027 (4) | 0.031 (3) | 0.100 (5) | −0.002 (3) | 0.002 (4) | −0.023 (4) |
O7 | 0.028 (4) | 0.031 (3) | 0.062 (4) | −0.009 (3) | 0.016 (3) | −0.015 (3) |
O8 | 0.030 (3) | 0.037 (3) | 0.033 (3) | −0.014 (3) | −0.011 (3) | 0.003 (3) |
P3 | 0.0270 (14) | 0.0228 (13) | 0.0348 (14) | −0.0084 (11) | −0.0026 (12) | 0.0000 (11) |
O9 | 0.046 (4) | 0.053 (4) | 0.030 (3) | −0.017 (3) | −0.014 (3) | 0.009 (3) |
O10 | 0.046 (4) | 0.031 (4) | 0.057 (4) | −0.003 (3) | 0.016 (4) | 0.002 (3) |
O11 | 0.040 (4) | 0.015 (3) | 0.048 (4) | −0.001 (3) | 0.007 (3) | −0.001 (3) |
O12 | 0.035 (4) | 0.049 (4) | 0.039 (4) | −0.020 (3) | −0.016 (3) | 0.005 (3) |
P4 | 0.0263 (14) | 0.0293 (13) | 0.0337 (14) | −0.0096 (12) | −0.0042 (12) | 0.0023 (11) |
O13 | 0.039 (4) | 0.058 (4) | 0.046 (4) | −0.025 (3) | −0.016 (3) | 0.011 (3) |
O14 | 0.025 (3) | 0.044 (4) | 0.027 (3) | −0.015 (3) | −0.001 (3) | 0.003 (3) |
O15 | 0.033 (4) | 0.033 (3) | 0.054 (4) | −0.002 (3) | 0.004 (3) | −0.011 (3) |
O16 | 0.031 (4) | 0.027 (3) | 0.068 (4) | −0.009 (3) | 0.007 (3) | −0.011 (3) |
P5 | 0.0366 (16) | 0.0589 (18) | 0.0601 (18) | −0.0238 (15) | −0.0208 (15) | 0.0146 (15) |
O17 | 0.047 (4) | 0.041 (4) | 0.072 (5) | −0.020 (3) | −0.011 (4) | −0.001 (3) |
O18 | 0.024 (4) | 0.082 (6) | 0.160 (8) | 0.006 (4) | 0.021 (5) | −0.007 (6) |
O19 | 0.062 (5) | 0.094 (5) | 0.046 (4) | −0.030 (4) | −0.024 (4) | 0.018 (4) |
O20 | 0.120 (6) | 0.209 (8) | 0.088 (5) | −0.133 (6) | −0.080 (5) | 0.092 (5) |
P6 | 0.0465 (17) | 0.106 (2) | 0.070 (2) | −0.0578 (17) | −0.0348 (16) | 0.0417 (18) |
O21 | 0.057 (4) | 0.105 (5) | 0.046 (4) | −0.053 (4) | −0.027 (4) | 0.027 (4) |
O22 | 0.118 (6) | 0.158 (7) | 0.088 (5) | −0.065 (5) | −0.039 (5) | 0.030 (5) |
O23 | 0.032 (5) | 0.128 (8) | 0.233 (11) | −0.014 (5) | 0.045 (6) | 0.080 (8) |
O24 | 0.132 (7) | 0.039 (4) | 0.051 (4) | −0.033 (4) | 0.011 (5) | −0.014 (3) |
C97 | 0.107 (12) | 0.269 (19) | 0.067 (9) | 0.076 (13) | −0.044 (8) | −0.064 (11) |
Cl1 | 0.195 (4) | 0.171 (4) | 0.082 (2) | −0.050 (3) | −0.051 (3) | −0.017 (3) |
Cl2 | 0.128 (3) | 0.226 (4) | 0.119 (3) | 0.023 (3) | −0.038 (3) | −0.102 (3) |
C98 | 0.058 (7) | 0.075 (7) | 0.033 (6) | −0.008 (6) | −0.016 (5) | 0.000 (5) |
Cl3 | 0.059 (2) | 0.078 (2) | 0.110 (2) | 0.0012 (18) | 0.0025 (19) | −0.0235 (19) |
Cl4 | 0.094 (2) | 0.095 (2) | 0.0618 (18) | 0.006 (2) | −0.0076 (18) | −0.0380 (17) |
C99 | 0.149 (12) | 0.152 (12) | 0.182 (12) | 0.086 (10) | −0.140 (10) | −0.092 (10) |
Cl5 | 0.130 (3) | 0.140 (3) | 0.149 (3) | 0.014 (3) | −0.075 (3) | −0.016 (3) |
Cl6 | 0.129 (3) | 0.149 (3) | 0.159 (3) | 0.051 (3) | −0.076 (3) | −0.083 (3) |
C100 | 0.112 (10) | 0.063 (8) | 0.109 (10) | −0.003 (8) | −0.039 (9) | −0.032 (7) |
Cl7 | 0.176 (4) | 0.127 (3) | 0.098 (3) | −0.035 (3) | −0.039 (3) | −0.018 (2) |
Cl8 | 0.275 (5) | 0.160 (4) | 0.140 (3) | 0.038 (4) | −0.104 (4) | −0.057 (3) |
C101 | 0.070 (8) | 0.060 (7) | 0.051 (6) | −0.007 (6) | −0.030 (6) | 0.007 (5) |
Cl9 | 0.183 (4) | 0.122 (3) | 0.081 (2) | −0.058 (3) | −0.023 (3) | −0.023 (2) |
Cl10 | 0.072 (2) | 0.101 (2) | 0.135 (3) | −0.016 (2) | −0.026 (2) | 0.044 (2) |
C102 | 0.056 (7) | 0.082 (8) | 0.046 (6) | −0.004 (6) | −0.025 (6) | −0.014 (6) |
Cl11 | 0.074 (2) | 0.096 (2) | 0.109 (3) | 0.002 (2) | 0.002 (2) | −0.027 (2) |
Cl12 | 0.0565 (18) | 0.0666 (17) | 0.0636 (18) | −0.0097 (15) | 0.0024 (15) | −0.0223 (15) |
C103 | 0.109 (9) | 0.083 (8) | 0.045 (6) | −0.018 (8) | −0.045 (7) | 0.016 (6) |
Cl13 | 0.090 (2) | 0.074 (2) | 0.089 (2) | 0.0000 (19) | −0.0295 (19) | 0.0091 (18) |
Cl14 | 0.091 (3) | 0.112 (3) | 0.122 (3) | −0.010 (2) | −0.034 (2) | −0.029 (2) |
C104 | 0.078 (11) | 0.276 (19) | 0.064 (8) | 0.007 (12) | −0.016 (8) | −0.055 (11) |
Cl15 | 0.106 (3) | 0.171 (4) | 0.154 (4) | −0.001 (3) | −0.013 (3) | −0.044 (3) |
Cl16 | 0.195 (5) | 0.484 (7) | 0.265 (5) | 0.099 (6) | −0.107 (4) | −0.252 (5) |
N1—C13 | 1.498 (9) | C65—C66 | 1.525 (10) |
N1—C9 | 1.513 (8) | C66—C67 | 1.530 (11) |
N1—C1 | 1.528 (9) | C67—C68 | 1.448 (13) |
N1—C5 | 1.535 (9) | C69—C70 | 1.499 (9) |
C1—C2 | 1.498 (9) | C70—C71 | 1.516 (10) |
C2—C3 | 1.537 (9) | C71—C72 | 1.508 (10) |
C3—C4 | 1.534 (10) | C73—C74 | 1.545 (10) |
C5—C6 | 1.494 (10) | C74—C75 | 1.514 (11) |
C6—C7 | 1.508 (11) | C75—C76 | 1.444 (11) |
C7—C8 | 1.504 (10) | C77—C78 | 1.512 (10) |
C9—C10 | 1.548 (11) | C78—C79 | 1.527 (10) |
C10—C11 | 1.479 (11) | C79—C80 | 1.504 (11) |
C11—C12 | 1.385 (13) | N6—C93 | 1.521 (9) |
C13—C14 | 1.506 (10) | N6—C89 | 1.523 (8) |
C14—C15 | 1.531 (10) | N6—C85 | 1.541 (9) |
C15—C16 | 1.509 (11) | N6—C81 | 1.545 (9) |
N2—C25 | 1.503 (8) | C81—C82 | 1.526 (9) |
N2—C29 | 1.518 (9) | C82—C83 | 1.533 (11) |
N2—C17 | 1.540 (8) | C83—C84 | 1.480 (11) |
N2—C21 | 1.531 (9) | C85—C86 | 1.523 (10) |
C17—C18 | 1.505 (10) | C86—C87 | 1.527 (10) |
C18—C19 | 1.544 (10) | C87—C88 | 1.508 (11) |
C19—C20 | 1.502 (10) | C89—C90 | 1.525 (11) |
C21—C22 | 1.519 (10) | C90—C91 | 1.495 (12) |
C22—C23 | 1.533 (10) | C91—C92 | 1.332 (14) |
C23—C24 | 1.519 (11) | C93—C94 | 1.511 (11) |
C25—C26 | 1.537 (9) | C94—C95 | 1.557 (12) |
C26—C27 | 1.519 (9) | C95—C96 | 1.538 (13) |
C27—C28 | 1.471 (10) | P1—O1 | 1.498 (5) |
C29—C30 | 1.518 (10) | P1—O3 | 1.514 (5) |
C30—C31 | 1.523 (11) | P1—O2 | 1.551 (6) |
C31—C32 | 1.496 (11) | P1—O4 | 1.546 (5) |
N3—C41 | 1.496 (9) | P2—O5 | 1.493 (6) |
N3—C45 | 1.514 (8) | P2—O6 | 1.511 (6) |
N3—C33 | 1.532 (9) | P2—O7 | 1.543 (5) |
N3—C37 | 1.536 (8) | P2—O8 | 1.563 (5) |
C33—C34 | 1.510 (10) | P3—O10 | 1.501 (5) |
C34—C35 | 1.535 (10) | P3—O12 | 1.514 (5) |
C35—C36 | 1.481 (10) | P3—O11 | 1.549 (5) |
C37—C38 | 1.513 (9) | P3—O9 | 1.563 (6) |
C38—C39 | 1.534 (9) | P4—O15 | 1.503 (5) |
C39—C40 | 1.516 (10) | P4—O13 | 1.510 (5) |
C41—C42 | 1.537 (9) | P4—O16 | 1.547 (5) |
C42—C43 | 1.500 (10) | P4—O14 | 1.575 (5) |
C43—C44 | 1.497 (10) | P5—O18 | 1.478 (7) |
C45—C46 | 1.464 (10) | P5—O19 | 1.524 (6) |
C46—C47 | 1.589 (12) | P5—O20 | 1.519 (7) |
C47—C48 | 1.409 (14) | P5—O17 | 1.546 (6) |
N4—C57 | 1.506 (8) | P6—O21 | 1.490 (6) |
N4—C53 | 1.516 (8) | P6—O24 | 1.499 (7) |
N4—C61 | 1.532 (9) | P6—O22 | 1.510 (7) |
N4—C49 | 1.543 (8) | P6—O23 | 1.540 (8) |
C49—C50 | 1.514 (10) | C97—Cl1 | 1.711 (7) |
C50—C51 | 1.539 (10) | C97—Cl2 | 1.734 (8) |
C51—C52 | 1.498 (11) | C98—Cl3 | 1.742 (9) |
C53—C54 | 1.507 (10) | C98—Cl4 | 1.747 (8) |
C54—C55 | 1.521 (10) | C99—Cl5 | 1.726 (10) |
C55—C56 | 1.494 (10) | C99—Cl6 | 1.765 (11) |
C57—C58 | 1.516 (9) | C100—Cl7 | 1.672 (10) |
C58—C59 | 1.520 (10) | C100—Cl8 | 1.739 (9) |
C59—C60 | 1.456 (11) | C101—Cl9 | 1.729 (9) |
C61—C62 | 1.492 (10) | C101—Cl10 | 1.779 (9) |
C62—C63 | 1.539 (11) | C102—Cl11 | 1.752 (9) |
C63—C64 | 1.443 (12) | C102—Cl12 | 1.762 (9) |
N5—C77 | 1.518 (9) | C103—Cl13 | 1.738 (9) |
N5—C73 | 1.507 (9) | C103—Cl14 | 1.764 (9) |
N5—C69 | 1.529 (8) | C104—Cl15 | 1.745 (11) |
N5—C65 | 1.533 (8) | C104—Cl16 | 1.767 (11) |
C13—N1—C9 | 111.2 (6) | C73—N5—C65 | 110.5 (6) |
C13—N1—C1 | 112.4 (6) | C69—N5—C65 | 106.4 (5) |
C9—N1—C1 | 106.4 (6) | C66—C65—N5 | 114.3 (6) |
C13—N1—C5 | 108.4 (6) | C65—C66—C67 | 110.4 (8) |
C9—N1—C5 | 109.1 (6) | C68—C67—C66 | 109.9 (9) |
C1—N1—C5 | 109.3 (6) | C70—C69—N5 | 116.4 (6) |
C2—C1—N1 | 114.0 (6) | C69—C70—C71 | 110.3 (7) |
C1—C2—C3 | 110.5 (6) | C72—C71—C70 | 110.9 (7) |
C4—C3—C2 | 112.2 (7) | N5—C73—C74 | 115.7 (7) |
C6—C5—N1 | 117.3 (7) | C75—C74—C73 | 111.7 (8) |
C5—C6—C7 | 113.6 (8) | C76—C75—C74 | 111.5 (8) |
C6—C7—C8 | 114.6 (8) | C78—C77—N5 | 116.8 (7) |
N1—C9—C10 | 115.9 (7) | C77—C78—C79 | 108.8 (7) |
C11—C10—C9 | 113.2 (9) | C80—C79—C78 | 113.2 (8) |
C12—C11—C10 | 115.9 (11) | C93—N6—C89 | 113.7 (7) |
N1—C13—C14 | 118.8 (7) | C93—N6—C85 | 106.0 (6) |
C13—C14—C15 | 111.1 (7) | C89—N6—C85 | 111.3 (6) |
C16—C15—C14 | 112.5 (8) | C93—N6—C81 | 111.8 (6) |
C25—N2—C29 | 110.7 (6) | C89—N6—C81 | 104.4 (6) |
C25—N2—C17 | 107.2 (6) | C85—N6—C81 | 109.7 (6) |
C29—N2—C17 | 109.9 (6) | C82—C81—N6 | 115.2 (7) |
C25—N2—C21 | 112.0 (6) | C81—C82—C83 | 106.6 (7) |
C29—N2—C21 | 105.8 (6) | C84—C83—C82 | 111.4 (9) |
C17—N2—C21 | 111.5 (6) | C86—C85—N6 | 115.9 (7) |
C18—C17—N2 | 115.0 (6) | C85—C86—C87 | 107.0 (7) |
C17—C18—C19 | 109.8 (7) | C88—C87—C86 | 112.3 (8) |
C20—C19—C18 | 112.8 (7) | C90—C89—N6 | 113.9 (7) |
C22—C21—N2 | 115.5 (6) | C91—C90—C89 | 112.5 (10) |
C21—C22—C23 | 109.4 (7) | C92—C91—C90 | 112.4 (12) |
C24—C23—C22 | 111.6 (7) | C94—C93—N6 | 115.4 (7) |
N2—C25—C26 | 117.2 (6) | C93—C94—C95 | 110.6 (9) |
C27—C26—C25 | 110.7 (6) | C96—C95—C94 | 106.5 (10) |
C28—C27—C26 | 112.7 (7) | O1—P1—O3 | 115.3 (4) |
C30—C29—N2 | 116.9 (7) | O1—P1—O2 | 111.3 (4) |
C29—C30—C31 | 111.1 (7) | O3—P1—O2 | 108.5 (3) |
C32—C31—C30 | 114.3 (8) | O1—P1—O4 | 107.5 (3) |
C41—N3—C45 | 110.6 (6) | O3—P1—O4 | 108.5 (3) |
C41—N3—C33 | 106.9 (6) | O2—P1—O4 | 105.3 (3) |
C45—N3—C33 | 109.8 (6) | O5—P2—O6 | 113.4 (4) |
C41—N3—C37 | 111.6 (6) | O5—P2—O7 | 109.3 (4) |
C45—N3—C37 | 107.6 (6) | O6—P2—O7 | 109.8 (3) |
C33—N3—C37 | 110.3 (6) | O5—P2—O8 | 109.5 (3) |
C34—C33—N3 | 115.5 (6) | O6—P2—O8 | 107.7 (3) |
C33—C34—C35 | 111.0 (7) | O7—P2—O8 | 106.8 (3) |
C36—C35—C34 | 112.9 (8) | O10—P3—O12 | 113.8 (4) |
C38—C37—N3 | 115.0 (6) | O10—P3—O11 | 109.7 (3) |
C37—C38—C39 | 109.8 (6) | O12—P3—O11 | 109.5 (3) |
C40—C39—C38 | 110.3 (7) | O10—P3—O9 | 110.2 (4) |
N3—C41—C42 | 118.2 (6) | O12—P3—O9 | 108.3 (3) |
C43—C42—C41 | 110.4 (7) | O11—P3—O9 | 105.0 (3) |
C44—C43—C42 | 112.9 (8) | O15—P4—O13 | 114.1 (4) |
C46—C45—N3 | 117.7 (7) | O15—P4—O16 | 109.5 (3) |
C45—C46—C47 | 110.1 (8) | O13—P4—O16 | 110.0 (3) |
C48—C47—C46 | 113.8 (13) | O15—P4—O14 | 110.0 (3) |
C57—N4—C53 | 107.5 (6) | O13—P4—O14 | 109.0 (3) |
C57—N4—C61 | 111.6 (6) | O16—P4—O14 | 103.9 (3) |
C53—N4—C61 | 111.4 (6) | O18—P5—O19 | 115.3 (5) |
C57—N4—C49 | 111.3 (5) | O18—P5—O20 | 106.6 (5) |
C53—N4—C49 | 111.2 (5) | O19—P5—O20 | 108.7 (4) |
C61—N4—C49 | 103.9 (5) | O18—P5—O17 | 108.9 (4) |
C50—C49—N4 | 114.8 (6) | O19—P5—O17 | 108.2 (4) |
C49—C50—C51 | 107.9 (7) | O20—P5—O17 | 109.1 (4) |
C52—C51—C50 | 111.8 (8) | O21—P6—O24 | 112.5 (4) |
C54—C53—N4 | 116.7 (6) | O21—P6—O22 | 107.8 (4) |
C53—C54—C55 | 108.4 (7) | O24—P6—O22 | 119.0 (5) |
C56—C55—C54 | 114.0 (8) | O21—P6—O23 | 108.9 (5) |
C58—C57—N4 | 117.9 (6) | O24—P6—O23 | 108.8 (4) |
C57—C58—C59 | 111.3 (7) | O22—P6—O23 | 98.6 (5) |
C60—C59—C58 | 112.3 (8) | Cl1—C97—Cl2 | 113.8 (5) |
C62—C61—N4 | 116.1 (7) | Cl3—C98—Cl4 | 111.4 (5) |
C61—C62—C63 | 107.2 (7) | Cl5—C99—Cl6 | 111.2 (7) |
C64—C63—C62 | 112.4 (10) | Cl7—C100—Cl8 | 109.9 (6) |
C77—N5—C73 | 106.6 (6) | Cl9—C101—Cl10 | 111.4 (5) |
C77—N5—C69 | 111.8 (6) | Cl11—C102—Cl12 | 111.3 (5) |
C73—N5—C69 | 111.3 (6) | Cl13—C103—Cl14 | 110.4 (5) |
C77—N5—C65 | 110.3 (6) | Cl15—C104—Cl16 | 109.3 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H02···O5 | 0.84 | 1.70 | 2.505 (7) | 160 |
O4—H04···O1i | 0.84 | 1.66 | 2.478 (7) | 165 |
O7—H07···O24 | 0.84 | 1.71 | 2.521 (7) | 163 |
O8—H08···O3 | 0.84 | 1.71 | 2.527 (6) | 164 |
O9—H09···O13 | 0.84 | 1.73 | 2.553 (6) | 167 |
O11—H011···O10ii | 0.84 | 1.70 | 2.518 (7) | 165 |
O14—H014···O12 | 0.84 | 1.73 | 2.551 (6) | 167 |
O16—H016···O18 | 0.84 | 1.77 | 2.529 (8) | 150 |
O17—H017···O15 | 0.84 | 1.71 | 2.541 (6) | 169 |
O20—H020···O21iii | 0.84 | 1.71 | 2.443 (9) | 144 |
O22—H022···O19iv | 0.84 | 2.04 | 2.625 (11) | 126 |
O23—H023···O6 | 0.84 | 1.70 | 2.448 (8) | 148 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) x, y−1, z; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17.33H40.67Cl2.67NO4P |
Mr | 452.68 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 16.1733 (3), 17.8443 (3), 26.7000 (5) |
α, β, γ (°) | 77.520 (3), 77.237 (3), 83.124 (3) |
V (Å3) | 7316.7 (2) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.50 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Nonius Kappa CCD Area-detector diffractometer |
Absorption correction | Multi-scans (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.816, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 58198, 22291, 10322 |
Rint | 0.100 |
θmax (°) | 24.1 |
(sin θ/λ)max (Å−1) | 0.575 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.156, 0.393, 1.93 |
No. of reflections | 22291 |
No. of parameters | 1417 |
No. of restraints | 878 |
H-atom treatment | H-atom parameters constrained |
(Δ/σ)max | 2.834 |
Δρmax, Δρmin (e Å−3) | 2.66, −1.47 |
Computer programs: COLLECT (Hooft, 1998), SCALEPACK (Otwinoski & Minor, 1997), COLLECT, DENZO (Otwinoski & Minor, 1997), COLLECT, maXus (Mackay et al., 1998), SHELXS 97 (Sheldrick, 1990), SHELXL 97 (Sheldrick, 1997), CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H02···O5 | 0.84 | 1.70 | 2.505 (7) | 160.0 |
O4—H04···O1i | 0.84 | 1.66 | 2.478 (7) | 165.4 |
O7—H07···O24 | 0.84 | 1.71 | 2.521 (7) | 162.9 |
O8—H08···O3 | 0.84 | 1.71 | 2.527 (6) | 163.6 |
O9—H09···O13 | 0.84 | 1.73 | 2.553 (6) | 166.5 |
O11—H011···O10ii | 0.84 | 1.70 | 2.518 (7) | 165.0 |
O14—H014···O12 | 0.84 | 1.73 | 2.551 (6) | 166.6 |
O16—H016···O18 | 0.84 | 1.77 | 2.529 (8) | 149.9 |
O17—H017···O15 | 0.84 | 1.71 | 2.541 (6) | 168.7 |
O20—H020···O21iii | 0.84 | 1.71 | 2.443 (9) | 143.9 |
O22—H022···O19iv | 0.84 | 2.04 | 2.625 (11) | 126.3 |
O23—H023···O6 | 0.84 | 1.70 | 2.448 (8) | 147.6 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) x, y−1, z; (iv) x, y+1, z. |
The development of receptors and sensors for anions is a rapidly developing area in supramolecular chemistry (Atwood et al., 1996; Beer & Gale, 2001; Beer & Smith, 1997; Bianchi et al., 1997; Davis et al., 1996; Kavallieratos et al., 1997; Schmidtchen & Berger, 1997; Sessler & Allen, 1999). In addition, anions have recently been exploited as templates for the formation of self-assembled supramolecular architectures in both organic and inorganic systems (Gale, 2000, 2001). It is possible to imagine how dihydrogenphosphate would oligomerize to form a coordination polymer. Tetrabutylammonium anion salts are frequently used as sources of anions, however the crystal structure of tetrabutylammonium dihydrogenphosphate has not, to the best of our knowledge, previously been elucidated. Anion chain assembly has been observed in other crystal structures (e.g. Karle & Karle, 1988), including the hydrated tetramethylammonium dihydrogenphosphate (Ohama et al., 1987) but not in the tetrabutylammonium salts that are commonly used in anion complexation studies.
The title compound, (I), crystallizes in a large triclinic cell with six tetrabutylammonium ions, six dihydrogenphosphate ions and eight dichloromethanes in the asymmetric unit. The dihydrogenphosphate ions donate and accept two hydrogen bonds to form an infinite chain and, although there are six independent ions in the asymmetric unit, the repeat length of the chain is 12 (Fig. 2). The tetrabutylammonium molecules can be seen to form cationic channels within which reside the infinite dihydrogenphosphate chains (Fig. 3).