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
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.013 Å
- R factor = 0.156
- wR factor = 0.393
- Data-to-parameter ratio = 15.7
checkCIF results
No syntax errors found
Alert Level A:
SHFSU_01 Alert A The absolute value of parameter shift to su ratio > 0.20 Absolute value of the parameter shift to su ratio given 2.834 Additional refinement cycles may be required.
Alert Level B:
DIFMX_01 Alert B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 2.659 Test value = 1.700 RFACG_01 Alert B The value of the R factor is > 0.15 R factor given 0.156 RFACR_01 Alert B The value of the weighted R factor is > 0.35 Weighted R factor given 0.393 THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5747 PLAT_112 Alert B ADDSYM Detects Additional (Pseudo) Symm. Elem. Z PLAT_214 Alert B Atom O23 (Anion/Solvent) ADP max/min Ratio 5.80 PLAT_360 Alert B Short C(sp3)-C(sp3) Bond C91 - C92 = 1.33 Ang.
Alert Level C:
DIFMN_02 Alert C The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -1.474 Test value = -1.275 DIFMN_03 Alert C The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT_213 Alert C Atom N1 has ADP max/min Ratio ........... 3.10 PLAT_213 Alert C Atom C84 has ADP max/min Ratio ........... 3.10 PLAT_213 Alert C Atom C91 has ADP max/min Ratio ........... 3.40 PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C11 - C12 = 1.38 Ang. PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C47 - C48 = 1.41 Ang. General Notes
ABSTY_01 Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. CELLZ_01 From the CIF: _cell_formula_units_Z 12 From the CIF: _chemical_formula_sum C17.33 H40.67 Cl2.67 N O4 P TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 207.96 208.00 -0.04 H 488.04 488.00 0.04 Cl 32.04 32.00 0.04 N 12.00 12.00 0.00 O 48.00 48.00 0.00 P 12.00 12.00 0.00 Difference between formula and atom_site contents detected. ALERT: check formula stoichiometry or atom site occupancies.
1 Alert Level A = Potentially serious problem
7 Alert Level B = Potential problem
8 Alert Level C = Please check
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. |
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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).