Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004987/cv6172sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004987/cv6172Isup2.hkl |
CCDC reference: 209966
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 11.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.228 Tmax scaled 0.990 Tmin scaled 0.945 REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.08 From the CIF: _reflns_number_total 17008 Count of symmetry unique reflns 10705 Completeness (_total/calc) 158.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 6303 Fraction of Friedel pairs measured 0.589 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
All chemicals were supplied by Aldrich and used as received. To a solution of 2,6-dihydroxybenzoic acid (2,6-Hdhb, 0.308 g, 2.00 mmol) and KOH (0.112 g, 2.00 mmol) in distilled water (ca 10 ml, pH = 3), Tb(NO3)3·4H2O (0.218 g, 0.50 mmol) was added and the mixture was stirred thoroughly for 1 h at ambient temperature. 5 ml of an aqueous solution containing tetrabutylammonium chloride hidrate (nBu4NCl.nH2O, 0.556 g, 2.00 mmol) was added to the resulting mixture, leading to the formation of a white flocculated precipitate. The supernant solution was decanted and allowed to stand undisturbed at ambient temperature for about two months, after which red crystals of the title compound were manually collected.
H atoms bound to C and O atoms were placed in calculated positions and allowed to ride during subsequent refinement with Uiso(H) = xUeq(C/O) (x = 1.5 for CH3 and x = 1.2 for the remaining H atoms). Carboxylic acid groups were assigned by examining the C—O distances, with the –OH H atoms being placed using the AFIX 147 instruction in SHELXL97 (Sheldrick, 1997). There is a pseudo-centre at (0,0,0). As no correlation coefficients > 0.5 were found, we conclude that no change of space group is needed. This was confirmed using ADDSYM routines in PLATON (Spek, 1990).
Data collection: COLLECT (Nonius 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare at al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C16H36N+·C7H5O4−·C7H6O4 | Z = 4 |
Mr = 549.69 | F(000) = 1192 |
Triclinic, P1 | Dx = 1.213 Mg m−3 |
a = 13.9840 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.0507 (2) Å | Cell parameters from 16891 reflections |
c = 15.4152 (4) Å | θ = 1.0–25.0° |
α = 86.201 (6)° | µ = 0.09 mm−1 |
β = 84.847 (7)° | T = 180 K |
γ = 89.898 (7)° | Block, red |
V = 3009.96 (11) Å3 | 0.23 × 0.16 × 0.12 mm |
Nonius KappaCCD diffractometer | 17008 independent reflections |
Radiation source: fine-focus sealed tube | 14232 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Thin–slice ω and ϕ scans | θmax = 25.1°, θmin = 3.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −16→16 |
Tmin = 0.770, Tmax = 0.806 | k = −16→16 |
26943 measured reflections | l = −18→18 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.3071P] where P = (Fo2 + 2Fc2)/3 |
17008 reflections | (Δ/σ)max = 0.006 |
1441 parameters | Δρmax = 0.17 e Å−3 |
3 restraints | Δρmin = −0.21 e Å−3 |
C16H36N+·C7H5O4−·C7H6O4 | γ = 89.898 (7)° |
Mr = 549.69 | V = 3009.96 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.9840 (3) Å | Mo Kα radiation |
b = 14.0507 (2) Å | µ = 0.09 mm−1 |
c = 15.4152 (4) Å | T = 180 K |
α = 86.201 (6)° | 0.23 × 0.16 × 0.12 mm |
β = 84.847 (7)° |
Nonius KappaCCD diffractometer | 17008 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 14232 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 0.806 | Rint = 0.029 |
26943 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 3 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.17 e Å−3 |
17008 reflections | Δρmin = −0.21 e Å−3 |
1441 parameters |
Experimental. There is a pseudo centre at (0,0,0). No correlation coefficients > 1/2, the space group IS P1(!). The –COOH hydrogen atoms were assigned by examining the C—O distances: all –OH hydrogen atoms were assigned with AFIX 14 (and so the positions of these atoms may NOT be reliable). Flack parameter found to be meaningless [0.3 (6)] with this being attributed to a crystal which is a weak anomalous scatterer (no atoms heavier than Si are found in the structure). The parameter has been omitted. |
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_1 | 0.2634 (2) | −0.02958 (17) | −0.24354 (16) | 0.0343 (6) | |
C1_1 | 0.2365 (3) | 0.0515 (2) | −0.3080 (2) | 0.0365 (8) | |
H1A_1 | 0.1852 | 0.0286 | −0.3417 | 0.044* | |
H1B_1 | 0.2932 | 0.0672 | −0.3497 | 0.044* | |
C2_1 | 0.2021 (3) | 0.1427 (2) | −0.2661 (2) | 0.0400 (8) | |
H2A_1 | 0.2540 | 0.1687 | −0.2349 | 0.048* | |
H2B_1 | 0.1463 | 0.1279 | −0.2231 | 0.048* | |
C3_1 | 0.1736 (3) | 0.2167 (2) | −0.3363 (2) | 0.0445 (9) | |
H3A_1 | 0.2290 | 0.2294 | −0.3802 | 0.053* | |
H3B_1 | 0.1206 | 0.1908 | −0.3664 | 0.053* | |
C4_1 | 0.1417 (3) | 0.3095 (2) | −0.2979 (2) | 0.0521 (10) | |
H4A_1 | 0.1215 | 0.3542 | −0.3443 | 0.078* | |
H4B_1 | 0.1951 | 0.3373 | −0.2711 | 0.078* | |
H4C_1 | 0.0877 | 0.2970 | −0.2535 | 0.078* | |
C5_1 | 0.3396 (3) | 0.0020 (2) | −0.1873 (2) | 0.0366 (8) | |
H5A_1 | 0.3535 | −0.0518 | −0.1457 | 0.044* | |
H5B_1 | 0.3134 | 0.0546 | −0.1529 | 0.044* | |
C6_1 | 0.4333 (3) | 0.0354 (2) | −0.2378 (2) | 0.0423 (8) | |
H6A_1 | 0.4206 | 0.0901 | −0.2789 | 0.051* | |
H6B_1 | 0.4606 | −0.0168 | −0.2723 | 0.051* | |
C7_1 | 0.5058 (3) | 0.0650 (3) | −0.1766 (2) | 0.0471 (9) | |
H7A_1 | 0.4803 | 0.1197 | −0.1445 | 0.057* | |
H7B_1 | 0.5161 | 0.0115 | −0.1334 | 0.057* | |
C8_1 | 0.6009 (3) | 0.0930 (3) | −0.2275 (3) | 0.0616 (11) | |
H8A_1 | 0.6477 | 0.1082 | −0.1868 | 0.092* | |
H8B_1 | 0.5916 | 0.1489 | −0.2673 | 0.092* | |
H8C_1 | 0.6248 | 0.0397 | −0.2612 | 0.092* | |
C9_1 | 0.2993 (3) | −0.1106 (2) | −0.2984 (2) | 0.0365 (8) | |
H9A_1 | 0.2469 | −0.1297 | −0.3328 | 0.044* | |
H9B_1 | 0.3528 | −0.0861 | −0.3404 | 0.044* | |
C10_1 | 0.3339 (3) | −0.1989 (2) | −0.2484 (2) | 0.0404 (8) | |
H10A_1 | 0.3879 | −0.1819 | −0.2150 | 0.048* | |
H10B_1 | 0.2812 | −0.2252 | −0.2065 | 0.048* | |
C11_1 | 0.3661 (3) | −0.2729 (2) | −0.3114 (2) | 0.0489 (9) | |
H11A_1 | 0.4198 | −0.2462 | −0.3519 | 0.059* | |
H11B_1 | 0.3125 | −0.2865 | −0.3466 | 0.059* | |
C12_1 | 0.3983 (3) | −0.3658 (3) | −0.2675 (3) | 0.0571 (10) | |
H12A_1 | 0.4175 | −0.4106 | −0.3119 | 0.086* | |
H12B_1 | 0.3453 | −0.3934 | −0.2279 | 0.086* | |
H12C_1 | 0.4530 | −0.3535 | −0.2342 | 0.086* | |
C13_1 | 0.1757 (2) | −0.0619 (2) | −0.1827 (2) | 0.0339 (7) | |
H13A_1 | 0.1944 | −0.1170 | −0.1445 | 0.041* | |
H13B_1 | 0.1570 | −0.0096 | −0.1447 | 0.041* | |
C14_1 | 0.0887 (3) | −0.0903 (2) | −0.2270 (2) | 0.0402 (8) | |
H14A_1 | 0.1090 | −0.1317 | −0.2747 | 0.048* | |
H14B_1 | 0.0588 | −0.0325 | −0.2528 | 0.048* | |
C15_1 | 0.0148 (3) | −0.1436 (2) | −0.1616 (2) | 0.0401 (8) | |
H15A_1 | 0.0433 | −0.2042 | −0.1400 | 0.048* | |
H15B_1 | 0.0000 | −0.1046 | −0.1110 | 0.048* | |
C16_1 | −0.0770 (3) | −0.1651 (3) | −0.2006 (3) | 0.0551 (10) | |
H16A_1 | −0.1219 | −0.1978 | −0.1560 | 0.083* | |
H16B_1 | −0.0633 | −0.2061 | −0.2492 | 0.083* | |
H16C_1 | −0.1057 | −0.1054 | −0.2221 | 0.083* | |
N1_2 | −0.26389 (19) | 0.03079 (17) | 0.24335 (16) | 0.0314 (6) | |
C1_2 | −0.3422 (3) | 0.0005 (2) | 0.1882 (2) | 0.0378 (8) | |
H1A_2 | −0.3596 | 0.0563 | 0.1502 | 0.045* | |
H1B_2 | −0.3157 | −0.0486 | 0.1497 | 0.045* | |
C2_2 | −0.4328 (3) | −0.0388 (3) | 0.2391 (2) | 0.0460 (9) | |
H2A_2 | −0.4160 | −0.0939 | 0.2782 | 0.055* | |
H2B_2 | −0.4614 | 0.0107 | 0.2761 | 0.055* | |
C3_2 | −0.5058 (3) | −0.0699 (3) | 0.1807 (2) | 0.0544 (10) | |
H3A_2 | −0.4779 | −0.1206 | 0.1447 | 0.065* | |
H3B_2 | −0.5218 | −0.0152 | 0.1408 | 0.065* | |
C4_2 | −0.5970 (3) | −0.1072 (3) | 0.2329 (3) | 0.0724 (13) | |
H4A_2 | −0.6412 | −0.1306 | 0.1932 | 0.109* | |
H4B_2 | −0.6277 | −0.0556 | 0.2649 | 0.109* | |
H4C_2 | −0.5810 | −0.1595 | 0.2744 | 0.109* | |
C5_2 | −0.3018 (2) | 0.1076 (2) | 0.3026 (2) | 0.0354 (7) | |
H5A_2 | −0.3581 | 0.0814 | 0.3400 | 0.043* | |
H5B_2 | −0.2517 | 0.1218 | 0.3414 | 0.043* | |
C6_2 | −0.3310 (3) | 0.2004 (2) | 0.2566 (2) | 0.0450 (9) | |
H6A_2 | −0.3717 | 0.1867 | 0.2095 | 0.054* | |
H6B_2 | −0.2730 | 0.2351 | 0.2298 | 0.054* | |
C7_2 | −0.3865 (3) | 0.2623 (2) | 0.3214 (2) | 0.0429 (8) | |
H7A_2 | −0.4469 | 0.2293 | 0.3444 | 0.052* | |
H7B_2 | −0.3478 | 0.2705 | 0.3712 | 0.052* | |
C8_2 | −0.4102 (3) | 0.3598 (3) | 0.2806 (3) | 0.0621 (11) | |
H8A_2 | −0.4480 | 0.3957 | 0.3239 | 0.093* | |
H8B_2 | −0.4473 | 0.3521 | 0.2306 | 0.093* | |
H8C_2 | −0.3505 | 0.3944 | 0.2611 | 0.093* | |
C9_2 | −0.1793 (2) | 0.0684 (2) | 0.18136 (19) | 0.0352 (8) | |
H9A_2 | −0.1609 | 0.0191 | 0.1400 | 0.042* | |
H9B_2 | −0.2006 | 0.1252 | 0.1468 | 0.042* | |
C10_2 | −0.0909 (2) | 0.0954 (2) | 0.2250 (2) | 0.0376 (8) | |
H10A_2 | −0.0607 | 0.0371 | 0.2496 | 0.045* | |
H10B_2 | −0.1099 | 0.1363 | 0.2735 | 0.045* | |
C11_2 | −0.0190 (2) | 0.1487 (2) | 0.1592 (2) | 0.0381 (8) | |
H11A_2 | −0.0480 | 0.2090 | 0.1377 | 0.046* | |
H11B_2 | −0.0040 | 0.1095 | 0.1087 | 0.046* | |
C12_2 | 0.0743 (3) | 0.1710 (3) | 0.1993 (2) | 0.0493 (9) | |
H12A_2 | 0.1154 | 0.2119 | 0.1575 | 0.074* | |
H12B_2 | 0.1079 | 0.1114 | 0.2131 | 0.074* | |
H12C_2 | 0.0591 | 0.2041 | 0.2528 | 0.074* | |
C13_2 | −0.2331 (3) | −0.0533 (2) | 0.3022 (2) | 0.0364 (8) | |
H13A_2 | −0.1806 | −0.0320 | 0.3354 | 0.044* | |
H13B_2 | −0.2879 | −0.0726 | 0.3448 | 0.044* | |
C14_2 | −0.1993 (3) | −0.1396 (2) | 0.2543 (2) | 0.0412 (8) | |
H14A_2 | −0.1466 | −0.1205 | 0.2093 | 0.049* | |
H14B_2 | −0.2528 | −0.1646 | 0.2244 | 0.049* | |
C15_2 | −0.1639 (3) | −0.2179 (3) | 0.3174 (2) | 0.0513 (10) | |
H15A_2 | −0.2160 | −0.2359 | 0.3633 | 0.062* | |
H15B_2 | −0.1091 | −0.1935 | 0.3460 | 0.062* | |
C16_2 | −0.1325 (3) | −0.3058 (3) | 0.2684 (3) | 0.0637 (12) | |
H16A_2 | −0.1064 | −0.3537 | 0.3089 | 0.096* | |
H16B_2 | −0.0831 | −0.2872 | 0.2212 | 0.096* | |
H16C_2 | −0.1880 | −0.3326 | 0.2438 | 0.096* | |
N1_3 | −0.2260 (2) | −0.53630 (18) | 0.73167 (16) | 0.0347 (6) | |
C1_3 | −0.2529 (3) | −0.4509 (2) | 0.6727 (2) | 0.0373 (8) | |
H1A_3 | −0.1957 | −0.4313 | 0.6330 | 0.045* | |
H1B_3 | −0.3028 | −0.4714 | 0.6361 | 0.045* | |
C2_3 | −0.2897 (3) | −0.3651 (2) | 0.7194 (2) | 0.0452 (9) | |
H2A_3 | −0.2383 | −0.3403 | 0.7521 | 0.054* | |
H2B_3 | −0.3445 | −0.3846 | 0.7620 | 0.054* | |
C3_3 | −0.3216 (3) | −0.2864 (3) | 0.6559 (2) | 0.0548 (10) | |
H3A_3 | −0.2681 | −0.2693 | 0.6112 | 0.066* | |
H3B_3 | −0.3758 | −0.3097 | 0.6259 | 0.066* | |
C4_3 | −0.3527 (4) | −0.1985 (3) | 0.7034 (3) | 0.0728 (13) | |
H4A_3 | −0.3739 | −0.1492 | 0.6614 | 0.109* | |
H4B_3 | −0.2985 | −0.1743 | 0.7317 | 0.109* | |
H4C_3 | −0.4058 | −0.2154 | 0.7476 | 0.109* | |
C5_3 | −0.1537 (3) | −0.5080 (2) | 0.7923 (2) | 0.0401 (8) | |
H5A_3 | −0.1397 | −0.5647 | 0.8307 | 0.048* | |
H5B_3 | −0.1835 | −0.4597 | 0.8301 | 0.048* | |
C6_3 | −0.0589 (3) | −0.4679 (3) | 0.7490 (2) | 0.0452 (9) | |
H6A_3 | −0.0713 | −0.4115 | 0.7096 | 0.054* | |
H6B_3 | −0.0262 | −0.5165 | 0.7134 | 0.054* | |
C7_3 | 0.0061 (3) | −0.4390 (3) | 0.8179 (3) | 0.0529 (10) | |
H7A_3 | −0.0266 | −0.3899 | 0.8528 | 0.063* | |
H7B_3 | 0.0171 | −0.4953 | 0.8579 | 0.063* | |
C8_3 | 0.1028 (3) | −0.3999 (3) | 0.7770 (3) | 0.0627 (11) | |
H8A_3 | 0.1406 | −0.3793 | 0.8229 | 0.094* | |
H8B_3 | 0.0922 | −0.3455 | 0.7359 | 0.094* | |
H8C_3 | 0.1376 | −0.4499 | 0.7459 | 0.094* | |
C9_3 | −0.1870 (2) | −0.6129 (2) | 0.6722 (2) | 0.0363 (7) | |
H9A_3 | −0.2357 | −0.6257 | 0.6316 | 0.044* | |
H9B_3 | −0.1290 | −0.5874 | 0.6368 | 0.044* | |
C10_3 | −0.1612 (3) | −0.7068 (2) | 0.7187 (2) | 0.0427 (8) | |
H10A_3 | −0.2203 | −0.7390 | 0.7463 | 0.051* | |
H10B_3 | −0.1192 | −0.6947 | 0.7652 | 0.051* | |
C11_3 | −0.1095 (3) | −0.7710 (2) | 0.6537 (2) | 0.0414 (8) | |
H11A_3 | −0.1486 | −0.7767 | 0.6038 | 0.050* | |
H11B_3 | −0.0472 | −0.7416 | 0.6310 | 0.050* | |
C12_3 | −0.0921 (3) | −0.8701 (3) | 0.6956 (3) | 0.0577 (10) | |
H12A_3 | −0.0610 | −0.9101 | 0.6517 | 0.087* | |
H12B_3 | −0.1536 | −0.8990 | 0.7191 | 0.087* | |
H12C_3 | −0.0506 | −0.8650 | 0.7431 | 0.087* | |
C13_3 | −0.3136 (2) | −0.5734 (2) | 0.7895 (2) | 0.0394 (8) | |
H13A_3 | −0.2938 | −0.6291 | 0.8263 | 0.047* | |
H13B_3 | −0.3350 | −0.5233 | 0.8290 | 0.047* | |
C14_3 | −0.3989 (2) | −0.6028 (2) | 0.7428 (2) | 0.0421 (8) | |
H14A_3 | −0.3790 | −0.6519 | 0.7017 | 0.051* | |
H14B_3 | −0.4234 | −0.5470 | 0.7091 | 0.051* | |
C15_3 | −0.4774 (3) | −0.6427 (3) | 0.8105 (2) | 0.0516 (9) | |
H15A_3 | −0.4529 | −0.7002 | 0.8419 | 0.062* | |
H15B_3 | −0.4932 | −0.5947 | 0.8537 | 0.062* | |
C16_3 | −0.5677 (3) | −0.6687 (3) | 0.7702 (3) | 0.0571 (10) | |
H16A_3 | −0.6150 | −0.6958 | 0.8159 | 0.086* | |
H16B_3 | −0.5524 | −0.7157 | 0.7269 | 0.086* | |
H16C_3 | −0.5942 | −0.6113 | 0.7418 | 0.086* | |
N1_4 | 0.2326 (2) | −0.47930 (17) | 0.24594 (16) | 0.0331 (6) | |
C1_4 | 0.1594 (3) | −0.5070 (2) | 0.1842 (2) | 0.0373 (8) | |
H1A_4 | 0.1503 | −0.4517 | 0.1425 | 0.045* | |
H1B_4 | 0.1867 | −0.5594 | 0.1500 | 0.045* | |
C2_4 | 0.0617 (3) | −0.5385 (2) | 0.2268 (2) | 0.0427 (8) | |
H2A_4 | 0.0329 | −0.4868 | 0.2610 | 0.051* | |
H2B_4 | 0.0690 | −0.5951 | 0.2673 | 0.051* | |
C3_4 | −0.0044 (3) | −0.5627 (3) | 0.1580 (2) | 0.0472 (9) | |
H3A_4 | −0.0096 | −0.5063 | 0.1166 | 0.057* | |
H3B_4 | 0.0244 | −0.6151 | 0.1246 | 0.057* | |
C4_4 | −0.1035 (3) | −0.5923 (3) | 0.1964 (3) | 0.0550 (10) | |
H4A_4 | −0.1414 | −0.6111 | 0.1498 | 0.083* | |
H4B_4 | −0.1347 | −0.5388 | 0.2250 | 0.083* | |
H4C_4 | −0.0987 | −0.6464 | 0.2393 | 0.083* | |
C5_4 | 0.1934 (3) | −0.3995 (2) | 0.3010 (2) | 0.0356 (7) | |
H5A_4 | 0.1360 | −0.4240 | 0.3380 | 0.043* | |
H5B_4 | 0.2423 | −0.3839 | 0.3406 | 0.043* | |
C6_4 | 0.1660 (3) | −0.3079 (2) | 0.2516 (2) | 0.0393 (8) | |
H6A_4 | 0.1133 | −0.3204 | 0.2150 | 0.047* | |
H6B_4 | 0.2218 | −0.2824 | 0.2130 | 0.047* | |
C7_4 | 0.1336 (3) | −0.2357 (2) | 0.3183 (2) | 0.0472 (9) | |
H7A_4 | 0.0783 | −0.2625 | 0.3567 | 0.057* | |
H7B_4 | 0.1865 | −0.2252 | 0.3552 | 0.057* | |
C8_4 | 0.1049 (3) | −0.1405 (3) | 0.2755 (2) | 0.0538 (10) | |
H8A_4 | 0.0814 | −0.0982 | 0.3207 | 0.081* | |
H8B_4 | 0.0541 | −0.1507 | 0.2373 | 0.081* | |
H8C_4 | 0.1608 | −0.1112 | 0.2410 | 0.081* | |
C9_4 | 0.3223 (2) | −0.4475 (2) | 0.1892 (2) | 0.0370 (8) | |
H9A_4 | 0.3044 | −0.3951 | 0.1477 | 0.044* | |
H9B_4 | 0.3445 | −0.5013 | 0.1544 | 0.044* | |
C10_4 | 0.4064 (3) | −0.4137 (2) | 0.2348 (2) | 0.0396 (8) | |
H10A_4 | 0.4274 | −0.4655 | 0.2754 | 0.047* | |
H10B_4 | 0.3868 | −0.3586 | 0.2690 | 0.047* | |
C11_4 | 0.4882 (3) | −0.3850 (3) | 0.1670 (2) | 0.0495 (9) | |
H11A_4 | 0.4668 | −0.3322 | 0.1277 | 0.059* | |
H11B_4 | 0.5046 | −0.4397 | 0.1312 | 0.059* | |
C12_4 | 0.5778 (3) | −0.3535 (3) | 0.2069 (3) | 0.0580 (10) | |
H12A_4 | 0.6293 | −0.3391 | 0.1605 | 0.087* | |
H12B_4 | 0.5984 | −0.4048 | 0.2473 | 0.087* | |
H12C_4 | 0.5634 | −0.2963 | 0.2387 | 0.087* | |
C13_4 | 0.2536 (3) | −0.5626 (2) | 0.3103 (2) | 0.0364 (8) | |
H13A_4 | 0.3021 | −0.5414 | 0.3479 | 0.044* | |
H13B_4 | 0.1941 | −0.5781 | 0.3484 | 0.044* | |
C14_4 | 0.2895 (3) | −0.6530 (2) | 0.2699 (2) | 0.0416 (8) | |
H14A_4 | 0.3465 | −0.6384 | 0.2283 | 0.050* | |
H14B_4 | 0.2389 | −0.6797 | 0.2375 | 0.050* | |
C15_4 | 0.3159 (3) | −0.7262 (2) | 0.3420 (2) | 0.0479 (9) | |
H15A_4 | 0.3689 | −0.7004 | 0.3722 | 0.057* | |
H15B_4 | 0.2599 | −0.7372 | 0.3855 | 0.057* | |
C16_4 | 0.3468 (3) | −0.8204 (2) | 0.3054 (3) | 0.0542 (10) | |
H16A_4 | 0.3677 | −0.8638 | 0.3523 | 0.081* | |
H16B_4 | 0.4001 | −0.8091 | 0.2600 | 0.081* | |
H16C_4 | 0.2926 | −0.8488 | 0.2801 | 0.081* | |
O1_5 | −0.16479 (16) | −0.74421 (14) | 0.40081 (15) | 0.0475 (6) | |
O2_5 | −0.01631 (16) | −0.77952 (14) | 0.43277 (15) | 0.0452 (5) | |
O3_5 | 0.09287 (15) | −0.65331 (16) | 0.47889 (16) | 0.0495 (6) | |
H3_5 | 0.0742 | −0.7085 | 0.4707 | 0.059* | |
O4_5 | −0.23063 (15) | −0.57666 (14) | 0.41932 (16) | 0.0492 (6) | |
H4_5 | −0.2287 | −0.6319 | 0.4015 | 0.059* | |
C17_5 | −0.0860 (2) | −0.7205 (2) | 0.42503 (19) | 0.0352 (7) | |
C18_5 | −0.0693 (2) | −0.62055 (19) | 0.44631 (18) | 0.0294 (6) | |
C19_5 | 0.0185 (2) | −0.5914 (2) | 0.47325 (19) | 0.0360 (7) | |
C20_5 | 0.0330 (2) | −0.4983 (2) | 0.4933 (2) | 0.0432 (8) | |
H20_5 | 0.0929 | −0.4792 | 0.5113 | 0.052* | |
C21_5 | −0.0413 (3) | −0.4329 (2) | 0.4868 (2) | 0.0421 (8) | |
H21_5 | −0.0314 | −0.3689 | 0.5004 | 0.050* | |
C22_5 | −0.1281 (2) | −0.45867 (19) | 0.46147 (19) | 0.0382 (7) | |
H22_5 | −0.1778 | −0.4129 | 0.4571 | 0.046* | |
C23_5 | −0.1435 (2) | −0.55281 (19) | 0.44192 (18) | 0.0333 (7) | |
O1_6 | −0.03573 (15) | −0.22777 (14) | 0.05184 (14) | 0.0438 (5) | |
O2_6 | −0.00883 (15) | −0.07585 (15) | 0.07788 (14) | 0.0426 (5) | |
O3_6 | 0.16122 (15) | −0.01071 (14) | 0.06250 (16) | 0.0451 (5) | |
H3_6 | 0.1009 | −0.0099 | 0.0687 | 0.054* | |
O4_6 | 0.10163 (18) | −0.33861 (14) | 0.01328 (16) | 0.0499 (6) | |
H4_6 | 0.0445 | −0.3212 | 0.0241 | 0.060* | |
C17_6 | 0.0210 (2) | −0.1565 (2) | 0.05794 (19) | 0.0353 (7) | |
C18_6 | 0.1252 (2) | −0.17378 (19) | 0.04054 (18) | 0.0308 (6) | |
C19_6 | 0.1914 (2) | −0.09906 (19) | 0.04468 (19) | 0.0340 (7) | |
C20_6 | 0.2895 (2) | −0.1149 (2) | 0.0301 (2) | 0.0393 (7) | |
H20_6 | 0.3340 | −0.0647 | 0.0344 | 0.047* | |
C21_6 | 0.3214 (2) | −0.2035 (2) | 0.0095 (2) | 0.0446 (8) | |
H21_6 | 0.3885 | −0.2141 | −0.0002 | 0.053* | |
C22_6 | 0.2589 (3) | −0.2782 (2) | 0.0024 (2) | 0.0444 (8) | |
H22_6 | 0.2828 | −0.3387 | −0.0131 | 0.053* | |
C23_6 | 0.1615 (2) | −0.2637 (2) | 0.01817 (19) | 0.0366 (7) | |
O1_7 | −0.47909 (16) | 0.27773 (15) | 0.54874 (15) | 0.0483 (6) | |
O2_7 | −0.32555 (17) | 0.24431 (14) | 0.56179 (15) | 0.0480 (6) | |
O3_7 | −0.26244 (15) | 0.07704 (15) | 0.53655 (17) | 0.0534 (6) | |
H3_7 | −0.2601 | 0.1356 | 0.5443 | 0.064* | |
O4_7 | −0.59779 (16) | 0.14733 (17) | 0.52605 (17) | 0.0530 (6) | |
H4_7 | −0.5789 | 0.2020 | 0.5359 | 0.064* | |
C17_7 | −0.4085 (2) | 0.2193 (2) | 0.54887 (19) | 0.0364 (7) | |
C18_7 | −0.4287 (2) | 0.1185 (2) | 0.53323 (18) | 0.0317 (6) | |
C19_7 | −0.3541 (2) | 0.0514 (2) | 0.52854 (19) | 0.0361 (7) | |
C20_7 | −0.3717 (2) | −0.0427 (2) | 0.5134 (2) | 0.0405 (7) | |
H20_7 | −0.3207 | −0.0874 | 0.5101 | 0.049* | |
C21_7 | −0.4641 (3) | −0.0704 (2) | 0.5034 (2) | 0.0478 (9) | |
H21_7 | −0.4765 | −0.1352 | 0.4940 | 0.057* | |
C22_7 | −0.5389 (3) | −0.0067 (2) | 0.5065 (2) | 0.0493 (9) | |
H22_7 | −0.6020 | −0.0272 | 0.4982 | 0.059* | |
C23_7 | −0.5219 (2) | 0.0869 (2) | 0.5218 (2) | 0.0366 (7) | |
O1_8 | 0.00825 (16) | 0.08204 (15) | −0.08965 (16) | 0.0473 (6) | |
O2_8 | 0.03590 (15) | 0.23358 (15) | −0.06628 (15) | 0.0462 (5) | |
O3_8 | −0.10064 (17) | 0.34459 (14) | −0.02561 (17) | 0.0506 (6) | |
H3_8 | −0.0438 | 0.3272 | −0.0380 | 0.061* | |
O4_8 | −0.16272 (15) | 0.01544 (14) | −0.06720 (17) | 0.0514 (6) | |
H4_8 | −0.1026 | 0.0149 | −0.0767 | 0.062* | |
C17_8 | −0.0215 (2) | 0.1622 (2) | −0.07012 (19) | 0.0356 (7) | |
C18_8 | −0.1255 (2) | 0.17943 (19) | −0.04952 (18) | 0.0293 (6) | |
C19_8 | −0.1611 (2) | 0.2688 (2) | −0.0269 (2) | 0.0374 (8) | |
C20_8 | −0.2579 (2) | 0.2828 (2) | −0.0062 (2) | 0.0444 (8) | |
H20_8 | −0.2808 | 0.3438 | 0.0087 | 0.053* | |
C21_8 | −0.3217 (2) | 0.2072 (2) | −0.0074 (2) | 0.0414 (8) | |
H21_8 | −0.3884 | 0.2169 | 0.0070 | 0.050* | |
C22_8 | −0.2893 (2) | 0.1185 (2) | −0.0291 (2) | 0.0373 (7) | |
H22_8 | −0.3336 | 0.0675 | −0.0305 | 0.045* | |
C23_8 | −0.1919 (2) | 0.10381 (19) | −0.04896 (19) | 0.0337 (7) | |
O1_9 | 0.32922 (17) | 0.11500 (15) | 0.06468 (19) | 0.0551 (7) | |
H1_9 | 0.2747 | 0.1245 | 0.0470 | 0.066* | |
O2_9 | 0.45440 (16) | 0.19712 (16) | 0.09249 (16) | 0.0507 (6) | |
O3_9 | 0.47039 (17) | 0.37574 (16) | 0.05605 (15) | 0.0466 (6) | |
H3_9 | 0.4857 | 0.3209 | 0.0751 | 0.056* | |
O4_9 | 0.20449 (17) | 0.19895 (14) | −0.02504 (16) | 0.0457 (6) | |
H4_9 | 0.1471 | 0.2086 | −0.0350 | 0.055* | |
C17_9 | 0.3768 (2) | 0.1971 (2) | 0.0605 (2) | 0.0416 (8) | |
C18_9 | 0.3363 (2) | 0.2834 (2) | 0.0185 (2) | 0.0321 (7) | |
C19_9 | 0.3863 (2) | 0.3707 (2) | 0.01794 (19) | 0.0367 (7) | |
C20_9 | 0.3516 (2) | 0.4540 (2) | −0.0201 (2) | 0.0403 (7) | |
H20_9 | 0.3863 | 0.5121 | −0.0204 | 0.048* | |
C21_9 | 0.2664 (2) | 0.4517 (2) | −0.0573 (2) | 0.0430 (8) | |
H21_9 | 0.2424 | 0.5091 | −0.0831 | 0.052* | |
C22_9 | 0.2136 (2) | 0.3677 (2) | −0.0585 (2) | 0.0408 (8) | |
H22_9 | 0.1539 | 0.3680 | −0.0835 | 0.049* | |
C23_9 | 0.2500 (2) | 0.28389 (19) | −0.0223 (2) | 0.0359 (7) | |
O1_10 | 0.64313 (16) | −0.40509 (16) | 0.43311 (17) | 0.0529 (6) | |
H1_10 | 0.6333 | −0.4628 | 0.4493 | 0.064* | |
O2_10 | 0.56134 (18) | −0.27413 (15) | 0.40982 (16) | 0.0547 (6) | |
O3_10 | 0.37916 (18) | −0.26742 (16) | 0.44035 (16) | 0.0518 (6) | |
H3_10 | 0.4347 | −0.2472 | 0.4237 | 0.062* | |
O4_10 | 0.55592 (16) | −0.54835 (15) | 0.51335 (16) | 0.0475 (6) | |
H4_10 | 0.5459 | −0.6064 | 0.5281 | 0.057* | |
C17_10 | 0.5607 (2) | −0.3587 (2) | 0.4382 (2) | 0.0424 (8) | |
C18_10 | 0.4722 (2) | −0.4073 (2) | 0.4753 (2) | 0.0351 (7) | |
C19_10 | 0.3841 (2) | −0.3587 (2) | 0.47495 (19) | 0.0384 (7) | |
C20_10 | 0.2989 (2) | −0.4020 (2) | 0.5093 (2) | 0.0439 (8) | |
H20_10 | 0.2402 | −0.3678 | 0.5093 | 0.053* | |
C21_10 | 0.3000 (2) | −0.4946 (2) | 0.5432 (2) | 0.0473 (8) | |
H21_10 | 0.2416 | −0.5243 | 0.5668 | 0.057* | |
C22_10 | 0.3853 (3) | −0.5461 (2) | 0.5437 (2) | 0.0461 (8) | |
H22_10 | 0.3849 | −0.6107 | 0.5663 | 0.055* | |
C23_10 | 0.4706 (2) | −0.5021 (2) | 0.5111 (2) | 0.0389 (8) | |
O1_11 | −0.14663 (17) | −0.09572 (16) | 0.55185 (18) | 0.0556 (6) | |
H1_11 | −0.1370 | −0.0411 | 0.5270 | 0.067* | |
O2_11 | −0.06656 (17) | −0.22533 (14) | 0.58346 (15) | 0.0497 (6) | |
O3_11 | −0.05504 (15) | 0.04496 (15) | 0.46953 (16) | 0.0456 (6) | |
H3_11 | −0.0450 | 0.1039 | 0.4608 | 0.055* | |
O4_11 | 0.11578 (18) | −0.23301 (15) | 0.56321 (15) | 0.0458 (6) | |
H4_11 | 0.0596 | −0.2511 | 0.5802 | 0.055* | |
C17_11 | −0.0642 (2) | −0.1421 (2) | 0.5527 (2) | 0.0413 (7) | |
C18_11 | 0.0257 (2) | −0.0938 (2) | 0.51872 (19) | 0.0329 (7) | |
C19_11 | 0.0300 (2) | −0.0008 (2) | 0.4779 (2) | 0.0368 (7) | |
C20_11 | 0.1170 (2) | 0.0412 (2) | 0.4479 (2) | 0.0423 (8) | |
H20_11 | 0.1193 | 0.1047 | 0.4224 | 0.051* | |
C21_11 | 0.2003 (2) | −0.0098 (2) | 0.4551 (2) | 0.0445 (8) | |
H21_11 | 0.2599 | 0.0188 | 0.4332 | 0.053* | |
C22_11 | 0.1995 (2) | −0.1013 (2) | 0.4933 (2) | 0.0421 (8) | |
H22_11 | 0.2580 | −0.1351 | 0.4976 | 0.051* | |
C23_11 | 0.1135 (2) | −0.1434 (2) | 0.52512 (19) | 0.0363 (7) | |
O1_12 | −0.33656 (17) | −0.10581 (15) | −0.05997 (19) | 0.0587 (7) | |
H1_12 | −0.2834 | −0.1153 | −0.0395 | 0.070* | |
O2_12 | −0.46151 (16) | −0.18679 (16) | −0.08952 (16) | 0.0508 (6) | |
O3_12 | −0.20570 (16) | −0.19384 (14) | 0.01712 (16) | 0.0449 (6) | |
H3_12 | −0.1514 | −0.2040 | 0.0350 | 0.054* | |
O4_12 | −0.46923 (17) | −0.36822 (16) | −0.07223 (15) | 0.0474 (6) | |
H4_12 | −0.4861 | −0.3128 | −0.0881 | 0.057* | |
C17_12 | −0.3819 (2) | −0.1880 (2) | −0.0615 (2) | 0.0405 (7) | |
C18_12 | −0.3365 (2) | −0.2762 (2) | −0.0306 (2) | 0.0346 (7) | |
C19_12 | −0.2487 (2) | −0.27868 (19) | 0.0063 (2) | 0.0376 (7) | |
C20_12 | −0.2071 (2) | −0.3639 (2) | 0.0328 (2) | 0.0440 (8) | |
H20_12 | −0.1466 | −0.3644 | 0.0565 | 0.053* | |
C21_12 | −0.2555 (2) | −0.4487 (2) | 0.0241 (2) | 0.0447 (8) | |
H21_12 | −0.2270 | −0.5075 | 0.0417 | 0.054* | |
C22_12 | −0.3433 (2) | −0.4497 (2) | −0.0091 (2) | 0.0422 (8) | |
H22_12 | −0.3761 | −0.5084 | −0.0125 | 0.051* | |
C23_12 | −0.3839 (2) | −0.3643 (2) | −0.03764 (19) | 0.0350 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1_1 | 0.0391 (17) | 0.0348 (14) | 0.0280 (14) | 0.0016 (11) | −0.0001 (12) | 0.0011 (10) |
C1_1 | 0.040 (2) | 0.0374 (17) | 0.0308 (17) | −0.0004 (14) | −0.0027 (14) | 0.0051 (13) |
C2_1 | 0.043 (2) | 0.0369 (17) | 0.0403 (18) | 0.0032 (14) | −0.0073 (15) | 0.0018 (13) |
C3_1 | 0.046 (2) | 0.0412 (19) | 0.045 (2) | 0.0069 (15) | −0.0040 (17) | 0.0050 (14) |
C4_1 | 0.055 (2) | 0.0425 (19) | 0.059 (2) | 0.0038 (16) | −0.0095 (18) | 0.0039 (16) |
C5_1 | 0.041 (2) | 0.0383 (17) | 0.0306 (17) | −0.0029 (14) | −0.0046 (15) | −0.0010 (13) |
C6_1 | 0.044 (2) | 0.047 (2) | 0.0361 (18) | −0.0048 (16) | −0.0046 (16) | −0.0013 (14) |
C7_1 | 0.044 (2) | 0.056 (2) | 0.042 (2) | −0.0099 (17) | −0.0129 (17) | 0.0076 (15) |
C8_1 | 0.056 (3) | 0.084 (3) | 0.046 (2) | −0.021 (2) | −0.0178 (19) | 0.0017 (19) |
C9_1 | 0.038 (2) | 0.0406 (17) | 0.0312 (16) | 0.0020 (14) | 0.0006 (14) | −0.0067 (13) |
C10_1 | 0.042 (2) | 0.0411 (18) | 0.0390 (19) | 0.0045 (14) | −0.0061 (15) | −0.0051 (13) |
C11_1 | 0.054 (2) | 0.048 (2) | 0.046 (2) | 0.0073 (16) | −0.0064 (17) | −0.0113 (15) |
C12_1 | 0.066 (3) | 0.047 (2) | 0.061 (2) | 0.0158 (17) | −0.012 (2) | −0.0114 (16) |
C13_1 | 0.0366 (19) | 0.0346 (16) | 0.0299 (16) | −0.0016 (13) | 0.0005 (14) | −0.0025 (12) |
C14_1 | 0.042 (2) | 0.0472 (19) | 0.0314 (17) | −0.0003 (15) | −0.0035 (15) | −0.0007 (13) |
C15_1 | 0.045 (2) | 0.0380 (17) | 0.0370 (18) | −0.0028 (14) | −0.0005 (16) | −0.0035 (13) |
C16_1 | 0.051 (3) | 0.064 (2) | 0.051 (2) | −0.0075 (18) | −0.0036 (19) | −0.0055 (18) |
N1_2 | 0.0327 (16) | 0.0338 (13) | 0.0282 (13) | −0.0020 (11) | −0.0052 (11) | −0.0028 (10) |
C1_2 | 0.040 (2) | 0.0383 (18) | 0.0363 (18) | −0.0024 (14) | −0.0087 (15) | −0.0041 (13) |
C2_2 | 0.042 (2) | 0.053 (2) | 0.044 (2) | −0.0091 (17) | −0.0047 (17) | −0.0034 (15) |
C3_2 | 0.054 (3) | 0.062 (2) | 0.047 (2) | −0.0172 (19) | −0.0142 (18) | 0.0091 (17) |
C4_2 | 0.049 (3) | 0.097 (3) | 0.072 (3) | −0.032 (2) | −0.015 (2) | 0.009 (2) |
C5_2 | 0.0347 (19) | 0.0403 (17) | 0.0314 (16) | 0.0001 (13) | −0.0016 (14) | −0.0049 (12) |
C6_2 | 0.052 (2) | 0.0404 (19) | 0.0420 (19) | 0.0076 (15) | 0.0002 (16) | −0.0037 (14) |
C7_2 | 0.039 (2) | 0.0445 (18) | 0.047 (2) | 0.0051 (14) | −0.0074 (15) | −0.0091 (14) |
C8_2 | 0.067 (3) | 0.048 (2) | 0.074 (3) | 0.0124 (19) | −0.014 (2) | −0.0089 (18) |
C9_2 | 0.039 (2) | 0.0373 (17) | 0.0283 (16) | 0.0020 (14) | −0.0018 (14) | 0.0021 (12) |
C10_2 | 0.0356 (19) | 0.0419 (17) | 0.0351 (17) | −0.0005 (14) | −0.0016 (14) | −0.0039 (13) |
C11_2 | 0.0338 (19) | 0.0386 (17) | 0.0413 (18) | 0.0000 (13) | 0.0006 (14) | −0.0043 (13) |
C12_2 | 0.039 (2) | 0.059 (2) | 0.049 (2) | −0.0098 (17) | −0.0002 (17) | −0.0064 (16) |
C13_2 | 0.037 (2) | 0.0386 (17) | 0.0329 (17) | 0.0018 (14) | −0.0052 (14) | 0.0037 (13) |
C14_2 | 0.045 (2) | 0.0385 (18) | 0.0392 (18) | 0.0021 (15) | −0.0021 (16) | 0.0007 (13) |
C15_2 | 0.058 (3) | 0.053 (2) | 0.040 (2) | 0.0079 (17) | 0.0058 (17) | 0.0072 (15) |
C16_2 | 0.088 (3) | 0.043 (2) | 0.057 (2) | 0.0205 (19) | 0.003 (2) | 0.0091 (16) |
N1_3 | 0.0350 (16) | 0.0402 (14) | 0.0282 (14) | 0.0006 (11) | −0.0005 (12) | −0.0006 (11) |
C1_3 | 0.0359 (19) | 0.0438 (18) | 0.0307 (17) | −0.0005 (14) | 0.0015 (14) | 0.0023 (13) |
C2_3 | 0.047 (2) | 0.048 (2) | 0.0405 (19) | 0.0057 (16) | −0.0057 (16) | 0.0003 (14) |
C3_3 | 0.067 (3) | 0.051 (2) | 0.043 (2) | 0.0143 (18) | 0.0097 (19) | 0.0057 (16) |
C4_3 | 0.095 (4) | 0.055 (2) | 0.064 (3) | 0.022 (2) | 0.004 (2) | 0.0074 (19) |
C5_3 | 0.042 (2) | 0.0448 (18) | 0.0344 (17) | −0.0002 (15) | −0.0065 (15) | −0.0031 (13) |
C6_3 | 0.043 (2) | 0.050 (2) | 0.043 (2) | −0.0040 (16) | −0.0058 (17) | −0.0057 (15) |
C7_3 | 0.047 (2) | 0.054 (2) | 0.059 (2) | −0.0063 (18) | −0.0170 (19) | −0.0005 (17) |
C8_3 | 0.050 (3) | 0.065 (2) | 0.075 (3) | −0.0061 (19) | −0.016 (2) | −0.003 (2) |
C9_3 | 0.0364 (19) | 0.0426 (17) | 0.0299 (16) | −0.0002 (14) | −0.0008 (14) | −0.0058 (13) |
C10_3 | 0.045 (2) | 0.0450 (19) | 0.0365 (18) | 0.0003 (15) | 0.0016 (16) | 0.0008 (14) |
C11_3 | 0.039 (2) | 0.0468 (19) | 0.0396 (18) | 0.0033 (14) | −0.0068 (15) | −0.0050 (14) |
C12_3 | 0.064 (3) | 0.053 (2) | 0.057 (2) | 0.0099 (18) | −0.010 (2) | −0.0010 (17) |
C13_3 | 0.040 (2) | 0.0464 (18) | 0.0308 (17) | −0.0041 (14) | 0.0032 (15) | −0.0033 (13) |
C14_3 | 0.039 (2) | 0.0511 (19) | 0.0351 (18) | −0.0003 (14) | 0.0041 (15) | −0.0035 (14) |
C15_3 | 0.046 (2) | 0.072 (2) | 0.0356 (19) | −0.0098 (17) | 0.0066 (16) | −0.0074 (16) |
C16_3 | 0.046 (2) | 0.071 (2) | 0.051 (2) | −0.0111 (18) | 0.0050 (19) | −0.0025 (18) |
N1_4 | 0.0355 (16) | 0.0371 (14) | 0.0264 (13) | 0.0007 (11) | −0.0017 (11) | −0.0027 (10) |
C1_4 | 0.042 (2) | 0.0383 (17) | 0.0318 (17) | −0.0008 (14) | −0.0067 (15) | −0.0023 (13) |
C2_4 | 0.040 (2) | 0.0449 (19) | 0.043 (2) | −0.0021 (15) | −0.0022 (16) | −0.0011 (15) |
C3_4 | 0.048 (2) | 0.047 (2) | 0.047 (2) | −0.0029 (16) | −0.0067 (17) | 0.0009 (15) |
C4_4 | 0.049 (2) | 0.059 (2) | 0.058 (2) | −0.0053 (17) | −0.0109 (19) | −0.0002 (17) |
C5_4 | 0.0386 (19) | 0.0399 (17) | 0.0286 (16) | 0.0009 (13) | −0.0020 (14) | −0.0045 (12) |
C6_4 | 0.048 (2) | 0.0401 (18) | 0.0298 (16) | 0.0050 (14) | −0.0015 (15) | −0.0039 (13) |
C7_4 | 0.063 (2) | 0.0447 (19) | 0.0345 (18) | 0.0119 (16) | −0.0045 (17) | −0.0088 (14) |
C8_4 | 0.071 (3) | 0.049 (2) | 0.042 (2) | 0.0144 (18) | −0.0072 (18) | −0.0091 (15) |
C9_4 | 0.042 (2) | 0.0379 (16) | 0.0296 (16) | 0.0004 (13) | 0.0011 (14) | 0.0004 (12) |
C10_4 | 0.042 (2) | 0.0445 (18) | 0.0315 (17) | −0.0005 (14) | 0.0003 (15) | −0.0034 (13) |
C11_4 | 0.046 (2) | 0.059 (2) | 0.0422 (19) | −0.0089 (16) | 0.0065 (16) | −0.0067 (15) |
C12_4 | 0.044 (2) | 0.077 (3) | 0.052 (2) | −0.0172 (18) | 0.0024 (18) | −0.0059 (18) |
C13_4 | 0.0377 (19) | 0.0394 (17) | 0.0309 (17) | 0.0006 (14) | −0.0017 (14) | 0.0052 (13) |
C14_4 | 0.042 (2) | 0.0409 (18) | 0.0409 (19) | 0.0000 (14) | −0.0009 (16) | 0.0002 (14) |
C15_4 | 0.048 (2) | 0.0472 (19) | 0.045 (2) | 0.0057 (15) | 0.0009 (17) | 0.0074 (15) |
C16_4 | 0.061 (3) | 0.044 (2) | 0.057 (2) | 0.0073 (16) | −0.0064 (19) | 0.0051 (16) |
O1_5 | 0.0443 (14) | 0.0381 (12) | 0.0621 (15) | −0.0014 (10) | −0.0114 (12) | −0.0077 (10) |
O2_5 | 0.0431 (14) | 0.0340 (11) | 0.0576 (14) | 0.0103 (10) | −0.0008 (11) | −0.0030 (9) |
O3_5 | 0.0309 (13) | 0.0542 (13) | 0.0631 (15) | 0.0058 (10) | −0.0076 (11) | 0.0025 (11) |
O4_5 | 0.0344 (13) | 0.0393 (12) | 0.0763 (17) | 0.0045 (9) | −0.0156 (11) | −0.0075 (11) |
C17_5 | 0.037 (2) | 0.0351 (17) | 0.0322 (16) | 0.0019 (14) | 0.0019 (14) | 0.0008 (12) |
C18_5 | 0.0294 (16) | 0.0320 (14) | 0.0257 (14) | −0.0007 (11) | 0.0022 (12) | 0.0009 (11) |
C19_5 | 0.0298 (18) | 0.0474 (19) | 0.0293 (16) | 0.0029 (14) | 0.0012 (13) | 0.0036 (13) |
C20_5 | 0.039 (2) | 0.0496 (19) | 0.0421 (19) | −0.0110 (16) | −0.0061 (17) | −0.0071 (14) |
C21_5 | 0.050 (2) | 0.0362 (17) | 0.0395 (18) | −0.0090 (14) | 0.0019 (16) | −0.0071 (13) |
C22_5 | 0.047 (2) | 0.0280 (15) | 0.0383 (17) | 0.0045 (13) | 0.0047 (15) | −0.0004 (12) |
C23_5 | 0.0304 (17) | 0.0355 (16) | 0.0327 (16) | −0.0017 (12) | 0.0006 (13) | 0.0034 (12) |
O1_6 | 0.0383 (13) | 0.0428 (13) | 0.0499 (14) | −0.0126 (10) | −0.0063 (11) | 0.0030 (10) |
O2_6 | 0.0342 (12) | 0.0423 (13) | 0.0514 (14) | 0.0042 (9) | −0.0028 (10) | −0.0055 (10) |
O3_6 | 0.0375 (13) | 0.0323 (11) | 0.0668 (15) | −0.0008 (9) | −0.0086 (12) | −0.0071 (10) |
O4_6 | 0.0572 (15) | 0.0331 (11) | 0.0605 (15) | −0.0042 (10) | −0.0099 (13) | −0.0050 (10) |
C17_6 | 0.0348 (19) | 0.0402 (18) | 0.0303 (16) | −0.0036 (14) | −0.0038 (14) | 0.0037 (13) |
C18_6 | 0.0308 (16) | 0.0327 (15) | 0.0285 (15) | 0.0005 (12) | −0.0020 (12) | 0.0006 (11) |
C19_6 | 0.0350 (18) | 0.0342 (16) | 0.0332 (16) | −0.0003 (12) | −0.0071 (14) | −0.0008 (12) |
C20_6 | 0.0330 (18) | 0.0440 (18) | 0.0406 (18) | −0.0031 (13) | −0.0047 (14) | 0.0026 (13) |
C21_6 | 0.0302 (19) | 0.062 (2) | 0.0392 (18) | 0.0086 (16) | 0.0036 (15) | 0.0037 (15) |
C22_6 | 0.048 (2) | 0.044 (2) | 0.0399 (19) | 0.0153 (17) | 0.0002 (16) | −0.0034 (15) |
C23_6 | 0.049 (2) | 0.0319 (16) | 0.0293 (16) | 0.0017 (14) | −0.0059 (15) | −0.0010 (12) |
O1_7 | 0.0428 (14) | 0.0407 (12) | 0.0606 (15) | 0.0136 (10) | −0.0009 (11) | −0.0036 (10) |
O2_7 | 0.0416 (14) | 0.0386 (12) | 0.0648 (15) | −0.0020 (10) | −0.0064 (11) | −0.0084 (10) |
O3_7 | 0.0290 (13) | 0.0387 (12) | 0.0925 (19) | 0.0002 (9) | −0.0058 (12) | −0.0030 (12) |
O4_7 | 0.0334 (13) | 0.0600 (14) | 0.0650 (16) | 0.0073 (10) | −0.0061 (11) | 0.0010 (12) |
C17_7 | 0.041 (2) | 0.0357 (17) | 0.0324 (17) | 0.0024 (14) | −0.0036 (14) | −0.0009 (12) |
C18_7 | 0.0296 (17) | 0.0381 (15) | 0.0265 (15) | 0.0004 (12) | −0.0011 (12) | 0.0015 (11) |
C19_7 | 0.0311 (18) | 0.0401 (17) | 0.0359 (17) | −0.0018 (13) | 0.0021 (13) | 0.0000 (12) |
C20_7 | 0.044 (2) | 0.0344 (16) | 0.0422 (18) | 0.0031 (13) | 0.0006 (15) | −0.0024 (13) |
C21_7 | 0.058 (2) | 0.0395 (19) | 0.047 (2) | −0.0077 (16) | −0.0072 (17) | −0.0057 (15) |
C22_7 | 0.043 (2) | 0.057 (2) | 0.049 (2) | −0.0185 (17) | −0.0095 (17) | 0.0015 (16) |
C23_7 | 0.0321 (18) | 0.0474 (19) | 0.0291 (16) | −0.0012 (14) | −0.0003 (14) | 0.0021 (13) |
O1_8 | 0.0349 (13) | 0.0418 (13) | 0.0653 (16) | 0.0037 (10) | −0.0006 (11) | −0.0089 (11) |
O2_8 | 0.0359 (13) | 0.0435 (12) | 0.0585 (15) | −0.0102 (10) | −0.0043 (11) | 0.0016 (10) |
O3_8 | 0.0507 (14) | 0.0310 (11) | 0.0706 (16) | −0.0059 (9) | −0.0084 (13) | −0.0034 (10) |
O4_8 | 0.0351 (13) | 0.0324 (12) | 0.0881 (18) | 0.0007 (9) | −0.0054 (13) | −0.0135 (11) |
C17_8 | 0.0355 (19) | 0.0373 (18) | 0.0336 (17) | −0.0051 (14) | −0.0048 (14) | 0.0021 (13) |
C18_8 | 0.0308 (16) | 0.0313 (15) | 0.0260 (15) | −0.0001 (11) | −0.0043 (12) | 0.0008 (11) |
C19_8 | 0.047 (2) | 0.0280 (16) | 0.0381 (18) | −0.0023 (14) | −0.0103 (15) | 0.0000 (12) |
C20_8 | 0.046 (2) | 0.0352 (17) | 0.052 (2) | 0.0100 (15) | −0.0024 (17) | −0.0086 (15) |
C21_8 | 0.0337 (19) | 0.0459 (19) | 0.0444 (19) | 0.0080 (14) | −0.0025 (15) | −0.0020 (14) |
C22_8 | 0.0339 (18) | 0.0373 (17) | 0.0410 (18) | −0.0023 (12) | −0.0066 (14) | 0.0003 (12) |
C23_8 | 0.0351 (18) | 0.0304 (16) | 0.0363 (17) | 0.0009 (12) | −0.0068 (14) | −0.0024 (12) |
O1_9 | 0.0421 (15) | 0.0393 (13) | 0.0845 (19) | −0.0059 (10) | −0.0176 (13) | 0.0081 (11) |
O2_9 | 0.0361 (14) | 0.0541 (14) | 0.0619 (15) | −0.0029 (10) | −0.0106 (12) | 0.0051 (11) |
O3_9 | 0.0383 (14) | 0.0469 (13) | 0.0560 (15) | −0.0083 (11) | −0.0083 (11) | −0.0085 (11) |
O4_9 | 0.0373 (14) | 0.0365 (12) | 0.0645 (15) | −0.0082 (10) | −0.0138 (12) | 0.0005 (10) |
C17_9 | 0.0342 (19) | 0.0406 (18) | 0.049 (2) | −0.0040 (14) | 0.0023 (16) | −0.0027 (14) |
C18_9 | 0.0302 (18) | 0.0330 (16) | 0.0319 (16) | −0.0025 (12) | 0.0044 (14) | −0.0039 (12) |
C19_9 | 0.0319 (18) | 0.0431 (17) | 0.0350 (17) | −0.0069 (13) | 0.0042 (14) | −0.0120 (13) |
C20_9 | 0.045 (2) | 0.0317 (16) | 0.0430 (18) | −0.0064 (13) | 0.0058 (15) | −0.0079 (13) |
C21_9 | 0.049 (2) | 0.0354 (16) | 0.0452 (19) | 0.0004 (14) | −0.0062 (16) | −0.0030 (13) |
C22_9 | 0.037 (2) | 0.0381 (18) | 0.048 (2) | −0.0034 (14) | −0.0100 (16) | −0.0007 (14) |
C23_9 | 0.0315 (17) | 0.0367 (17) | 0.0392 (18) | −0.0073 (14) | 0.0016 (14) | −0.0061 (13) |
O1_10 | 0.0411 (14) | 0.0428 (13) | 0.0742 (17) | 0.0056 (11) | −0.0020 (12) | −0.0029 (12) |
O2_10 | 0.0608 (16) | 0.0353 (13) | 0.0662 (16) | 0.0048 (10) | 0.0037 (13) | −0.0033 (11) |
O3_10 | 0.0534 (16) | 0.0406 (13) | 0.0623 (16) | 0.0131 (11) | −0.0106 (13) | −0.0027 (11) |
O4_10 | 0.0402 (14) | 0.0376 (12) | 0.0638 (16) | 0.0121 (10) | −0.0060 (11) | 0.0044 (11) |
C17_10 | 0.049 (2) | 0.0365 (18) | 0.0432 (18) | 0.0104 (15) | −0.0053 (15) | −0.0118 (13) |
C18_10 | 0.0397 (19) | 0.0326 (16) | 0.0345 (16) | 0.0055 (13) | −0.0082 (14) | −0.0084 (12) |
C19_10 | 0.048 (2) | 0.0360 (17) | 0.0340 (17) | 0.0104 (14) | −0.0133 (15) | −0.0103 (12) |
C20_10 | 0.038 (2) | 0.0477 (19) | 0.048 (2) | 0.0119 (14) | −0.0126 (16) | −0.0101 (14) |
C21_10 | 0.039 (2) | 0.053 (2) | 0.051 (2) | 0.0019 (15) | −0.0073 (16) | −0.0068 (15) |
C22_10 | 0.045 (2) | 0.0378 (18) | 0.056 (2) | 0.0080 (15) | −0.0082 (17) | −0.0025 (15) |
C23_10 | 0.040 (2) | 0.0383 (16) | 0.0407 (19) | 0.0096 (15) | −0.0097 (15) | −0.0076 (13) |
O1_11 | 0.0408 (14) | 0.0398 (13) | 0.0834 (19) | 0.0054 (10) | 0.0037 (12) | 0.0040 (12) |
O2_11 | 0.0532 (15) | 0.0317 (12) | 0.0624 (15) | 0.0030 (10) | 0.0025 (12) | −0.0018 (10) |
O3_11 | 0.0355 (13) | 0.0345 (12) | 0.0660 (16) | 0.0079 (9) | −0.0028 (11) | 0.0007 (11) |
O4_11 | 0.0497 (15) | 0.0356 (12) | 0.0520 (14) | 0.0098 (10) | −0.0072 (12) | 0.0009 (10) |
C17_11 | 0.044 (2) | 0.0346 (17) | 0.0459 (19) | 0.0054 (14) | −0.0031 (15) | −0.0091 (13) |
C18_11 | 0.0334 (18) | 0.0343 (16) | 0.0315 (16) | 0.0053 (13) | −0.0018 (13) | −0.0083 (12) |
C19_11 | 0.040 (2) | 0.0339 (16) | 0.0381 (18) | 0.0075 (15) | −0.0059 (15) | −0.0088 (13) |
C20_11 | 0.039 (2) | 0.0373 (17) | 0.050 (2) | 0.0030 (14) | −0.0028 (15) | 0.0007 (14) |
C21_11 | 0.0326 (19) | 0.0474 (19) | 0.054 (2) | 0.0021 (14) | −0.0063 (15) | −0.0028 (15) |
C22_11 | 0.0332 (19) | 0.0483 (19) | 0.0473 (19) | 0.0095 (14) | −0.0122 (15) | −0.0106 (14) |
C23_11 | 0.044 (2) | 0.0342 (16) | 0.0329 (16) | 0.0089 (13) | −0.0094 (14) | −0.0092 (12) |
O1_12 | 0.0429 (15) | 0.0353 (13) | 0.099 (2) | −0.0043 (10) | −0.0175 (14) | 0.0039 (11) |
O2_12 | 0.0302 (13) | 0.0528 (13) | 0.0688 (16) | −0.0034 (10) | −0.0074 (12) | 0.0046 (11) |
O3_12 | 0.0366 (14) | 0.0329 (12) | 0.0662 (16) | −0.0088 (9) | −0.0123 (12) | −0.0009 (10) |
O4_12 | 0.0390 (15) | 0.0537 (14) | 0.0504 (14) | −0.0114 (11) | −0.0090 (11) | −0.0034 (11) |
C17_12 | 0.0309 (19) | 0.0431 (18) | 0.0462 (19) | −0.0054 (13) | 0.0021 (15) | −0.0021 (13) |
C18_12 | 0.0311 (18) | 0.0360 (16) | 0.0363 (17) | −0.0043 (12) | 0.0010 (14) | −0.0052 (12) |
C19_12 | 0.0359 (18) | 0.0348 (18) | 0.0416 (18) | −0.0065 (15) | 0.0022 (15) | −0.0061 (14) |
C20_12 | 0.041 (2) | 0.0398 (18) | 0.052 (2) | −0.0035 (14) | −0.0067 (16) | −0.0039 (14) |
C21_12 | 0.053 (2) | 0.0319 (16) | 0.050 (2) | −0.0014 (14) | −0.0064 (17) | −0.0032 (13) |
C22_12 | 0.049 (2) | 0.0337 (17) | 0.0441 (19) | −0.0099 (13) | 0.0019 (16) | −0.0101 (13) |
C23_12 | 0.0314 (18) | 0.0442 (17) | 0.0293 (16) | −0.0072 (13) | 0.0011 (14) | −0.0062 (12) |
N1_1—C5_1 | 1.518 (4) | C4_4—H4B_4 | 0.9800 |
N1_1—C9_1 | 1.521 (4) | C4_4—H4C_4 | 0.9800 |
N1_1—C13_1 | 1.526 (4) | C5_4—C6_4 | 1.517 (4) |
N1_1—C1_1 | 1.530 (4) | C5_4—H5A_4 | 0.9900 |
C1_1—C2_1 | 1.530 (5) | C5_4—H5B_4 | 0.9900 |
C1_1—H1A_1 | 0.9900 | C6_4—C7_4 | 1.531 (4) |
C1_1—H1B_1 | 0.9900 | C6_4—H6A_4 | 0.9900 |
C2_1—C3_1 | 1.530 (4) | C6_4—H6B_4 | 0.9900 |
C2_1—H2A_1 | 0.9900 | C7_4—C8_4 | 1.522 (5) |
C2_1—H2B_1 | 0.9900 | C7_4—H7A_4 | 0.9900 |
C3_1—C4_1 | 1.517 (5) | C7_4—H7B_4 | 0.9900 |
C3_1—H3A_1 | 0.9900 | C8_4—H8A_4 | 0.9800 |
C3_1—H3B_1 | 0.9900 | C8_4—H8B_4 | 0.9800 |
C4_1—H4A_1 | 0.9800 | C8_4—H8C_4 | 0.9800 |
C4_1—H4B_1 | 0.9800 | C9_4—C10_4 | 1.514 (5) |
C4_1—H4C_1 | 0.9800 | C9_4—H9A_4 | 0.9900 |
C5_1—C6_1 | 1.521 (5) | C9_4—H9B_4 | 0.9900 |
C5_1—H5A_1 | 0.9900 | C10_4—C11_4 | 1.516 (5) |
C5_1—H5B_1 | 0.9900 | C10_4—H10A_4 | 0.9900 |
C6_1—C7_1 | 1.522 (5) | C10_4—H10B_4 | 0.9900 |
C6_1—H6A_1 | 0.9900 | C11_4—C12_4 | 1.524 (6) |
C6_1—H6B_1 | 0.9900 | C11_4—H11A_4 | 0.9900 |
C7_1—C8_1 | 1.521 (5) | C11_4—H11B_4 | 0.9900 |
C7_1—H7A_1 | 0.9900 | C12_4—H12A_4 | 0.9800 |
C7_1—H7B_1 | 0.9900 | C12_4—H12B_4 | 0.9800 |
C8_1—H8A_1 | 0.9800 | C12_4—H12C_4 | 0.9800 |
C8_1—H8B_1 | 0.9800 | C13_4—C14_4 | 1.517 (5) |
C8_1—H8C_1 | 0.9800 | C13_4—H13A_4 | 0.9900 |
C9_1—C10_1 | 1.518 (4) | C13_4—H13B_4 | 0.9900 |
C9_1—H9A_1 | 0.9900 | C14_4—C15_4 | 1.533 (5) |
C9_1—H9B_1 | 0.9900 | C14_4—H14A_4 | 0.9900 |
C10_1—C11_1 | 1.511 (5) | C14_4—H14B_4 | 0.9900 |
C10_1—H10A_1 | 0.9900 | C15_4—C16_4 | 1.520 (5) |
C10_1—H10B_1 | 0.9900 | C15_4—H15A_4 | 0.9900 |
C11_1—C12_1 | 1.517 (5) | C15_4—H15B_4 | 0.9900 |
C11_1—H11A_1 | 0.9900 | C16_4—H16A_4 | 0.9800 |
C11_1—H11B_1 | 0.9900 | C16_4—H16B_4 | 0.9800 |
C12_1—H12A_1 | 0.9800 | C16_4—H16C_4 | 0.9800 |
C12_1—H12B_1 | 0.9800 | O1_5—C17_5 | 1.247 (4) |
C12_1—H12C_1 | 0.9800 | O2_5—C17_5 | 1.288 (4) |
C13_1—C14_1 | 1.514 (5) | O3_5—C19_5 | 1.359 (4) |
C13_1—H13A_1 | 0.9900 | O3_5—H3_5 | 0.8400 |
C13_1—H13B_1 | 0.9900 | O4_5—C23_5 | 1.346 (4) |
C14_1—C15_1 | 1.535 (5) | O4_5—H4_5 | 0.8400 |
C14_1—H14A_1 | 0.9900 | C17_5—C18_5 | 1.486 (4) |
C14_1—H14B_1 | 0.9900 | C18_5—C19_5 | 1.402 (4) |
C15_1—C16_1 | 1.506 (5) | C18_5—C23_5 | 1.409 (4) |
C15_1—H15A_1 | 0.9900 | C19_5—C20_5 | 1.384 (4) |
C15_1—H15B_1 | 0.9900 | C20_5—C21_5 | 1.392 (5) |
C16_1—H16A_1 | 0.9800 | C20_5—H20_5 | 0.9500 |
C16_1—H16B_1 | 0.9800 | C21_5—C22_5 | 1.365 (5) |
C16_1—H16C_1 | 0.9800 | C21_5—H21_5 | 0.9500 |
N1_2—C5_2 | 1.523 (4) | C22_5—C23_5 | 1.397 (4) |
N1_2—C1_2 | 1.524 (4) | C22_5—H22_5 | 0.9500 |
N1_2—C9_2 | 1.524 (4) | O1_6—C17_6 | 1.292 (4) |
N1_2—C13_2 | 1.527 (4) | O2_6—C17_6 | 1.254 (4) |
C1_2—C2_2 | 1.514 (5) | O3_6—C19_6 | 1.348 (3) |
C1_2—H1A_2 | 0.9900 | O3_6—H3_6 | 0.8400 |
C1_2—H1B_2 | 0.9900 | O4_6—C23_6 | 1.356 (4) |
C2_2—C3_2 | 1.505 (5) | O4_6—H4_6 | 0.8400 |
C2_2—H2A_2 | 0.9900 | C17_6—C18_6 | 1.481 (4) |
C2_2—H2B_2 | 0.9900 | C18_6—C19_6 | 1.409 (4) |
C3_2—C4_2 | 1.521 (6) | C18_6—C23_6 | 1.413 (4) |
C3_2—H3A_2 | 0.9900 | C19_6—C20_6 | 1.391 (4) |
C3_2—H3B_2 | 0.9900 | C20_6—C21_6 | 1.370 (4) |
C4_2—H4A_2 | 0.9800 | C20_6—H20_6 | 0.9500 |
C4_2—H4B_2 | 0.9800 | C21_6—C22_6 | 1.382 (5) |
C4_2—H4C_2 | 0.9800 | C21_6—H21_6 | 0.9500 |
C5_2—C6_2 | 1.515 (5) | C22_6—C23_6 | 1.380 (5) |
C5_2—H5A_2 | 0.9900 | C22_6—H22_6 | 0.9500 |
C5_2—H5B_2 | 0.9900 | O1_7—C17_7 | 1.283 (4) |
C6_2—C7_2 | 1.526 (5) | O2_7—C17_7 | 1.249 (4) |
C6_2—H6A_2 | 0.9900 | O3_7—C19_7 | 1.351 (4) |
C6_2—H6B_2 | 0.9900 | O3_7—H3_7 | 0.8400 |
C7_2—C8_2 | 1.517 (5) | O4_7—C23_7 | 1.358 (4) |
C7_2—H7A_2 | 0.9900 | O4_7—H4_7 | 0.8400 |
C7_2—H7B_2 | 0.9900 | C17_7—C18_7 | 1.484 (4) |
C8_2—H8A_2 | 0.9800 | C18_7—C19_7 | 1.405 (4) |
C8_2—H8B_2 | 0.9800 | C18_7—C23_7 | 1.408 (4) |
C8_2—H8C_2 | 0.9800 | C19_7—C20_7 | 1.383 (4) |
C9_2—C10_2 | 1.520 (5) | C20_7—C21_7 | 1.375 (5) |
C9_2—H9A_2 | 0.9900 | C20_7—H20_7 | 0.9500 |
C9_2—H9B_2 | 0.9900 | C21_7—C22_7 | 1.376 (5) |
C10_2—C11_2 | 1.522 (4) | C21_7—H21_7 | 0.9500 |
C10_2—H10A_2 | 0.9900 | C22_7—C23_7 | 1.377 (4) |
C10_2—H10B_2 | 0.9900 | C22_7—H22_7 | 0.9500 |
C11_2—C12_2 | 1.534 (5) | O1_8—C17_8 | 1.246 (4) |
C11_2—H11A_2 | 0.9900 | O2_8—C17_8 | 1.293 (4) |
C11_2—H11B_2 | 0.9900 | O3_8—C19_8 | 1.363 (4) |
C12_2—H12A_2 | 0.9800 | O3_8—H3_8 | 0.8400 |
C12_2—H12B_2 | 0.9800 | O4_8—C23_8 | 1.346 (3) |
C12_2—H12C_2 | 0.9800 | O4_8—H4_8 | 0.8400 |
C13_2—C14_2 | 1.513 (5) | C17_8—C18_8 | 1.484 (4) |
C13_2—H13A_2 | 0.9900 | C18_8—C19_8 | 1.404 (4) |
C13_2—H13B_2 | 0.9900 | C18_8—C23_8 | 1.411 (4) |
C14_2—C15_2 | 1.531 (5) | C19_8—C20_8 | 1.379 (5) |
C14_2—H14A_2 | 0.9900 | C20_8—C21_8 | 1.390 (5) |
C14_2—H14B_2 | 0.9900 | C20_8—H20_8 | 0.9500 |
C15_2—C16_2 | 1.533 (5) | C21_8—C22_8 | 1.378 (4) |
C15_2—H15A_2 | 0.9900 | C21_8—H21_8 | 0.9500 |
C15_2—H15B_2 | 0.9900 | C22_8—C23_8 | 1.388 (4) |
C16_2—H16A_2 | 0.9800 | C22_8—H22_8 | 0.9500 |
C16_2—H16B_2 | 0.9800 | O1_9—C17_9 | 1.328 (4) |
C16_2—H16C_2 | 0.9800 | O1_9—H1_9 | 0.8400 |
N1_3—C5_3 | 1.509 (4) | O2_9—C17_9 | 1.231 (4) |
N1_3—C13_3 | 1.520 (4) | O3_9—C19_9 | 1.365 (4) |
N1_3—C1_3 | 1.524 (4) | O3_9—H3_9 | 0.8400 |
N1_3—C9_3 | 1.528 (4) | O4_9—C23_9 | 1.358 (4) |
C1_3—C2_3 | 1.512 (5) | O4_9—H4_9 | 0.8400 |
C1_3—H1A_3 | 0.9900 | C17_9—C18_9 | 1.473 (4) |
C1_3—H1B_3 | 0.9900 | C18_9—C23_9 | 1.411 (4) |
C2_3—C3_3 | 1.521 (5) | C18_9—C19_9 | 1.413 (4) |
C2_3—H2A_3 | 0.9900 | C19_9—C20_9 | 1.381 (4) |
C2_3—H2B_3 | 0.9900 | C20_9—C21_9 | 1.370 (5) |
C3_3—C4_3 | 1.519 (5) | C20_9—H20_9 | 0.9500 |
C3_3—H3A_3 | 0.9900 | C21_9—C22_9 | 1.395 (4) |
C3_3—H3B_3 | 0.9900 | C21_9—H21_9 | 0.9500 |
C4_3—H4A_3 | 0.9800 | C22_9—C23_9 | 1.385 (4) |
C4_3—H4B_3 | 0.9800 | C22_9—H22_9 | 0.9500 |
C4_3—H4C_3 | 0.9800 | O1_10—C17_10 | 1.322 (4) |
C5_3—C6_3 | 1.521 (5) | O1_10—H1_10 | 0.8400 |
C5_3—H5A_3 | 0.9900 | O2_10—C17_10 | 1.238 (4) |
C5_3—H5B_3 | 0.9900 | O3_10—C19_10 | 1.360 (4) |
C6_3—C7_3 | 1.533 (5) | O3_10—H3_10 | 0.8400 |
C6_3—H6A_3 | 0.9900 | O4_10—C23_10 | 1.360 (4) |
C6_3—H6B_3 | 0.9900 | O4_10—H4_10 | 0.8400 |
C7_3—C8_3 | 1.526 (6) | C17_10—C18_10 | 1.466 (4) |
C7_3—H7A_3 | 0.9900 | C18_10—C23_10 | 1.407 (4) |
C7_3—H7B_3 | 0.9900 | C18_10—C19_10 | 1.408 (4) |
C8_3—H8A_3 | 0.9800 | C19_10—C20_10 | 1.385 (5) |
C8_3—H8B_3 | 0.9800 | C20_10—C21_10 | 1.371 (4) |
C8_3—H8C_3 | 0.9800 | C20_10—H20_10 | 0.9500 |
C9_3—C10_3 | 1.518 (4) | C21_10—C22_10 | 1.394 (4) |
C9_3—H9A_3 | 0.9900 | C21_10—H21_10 | 0.9500 |
C9_3—H9B_3 | 0.9900 | C22_10—C23_10 | 1.382 (4) |
C10_3—C11_3 | 1.526 (5) | C22_10—H22_10 | 0.9500 |
C10_3—H10A_3 | 0.9900 | O1_11—C17_11 | 1.324 (4) |
C10_3—H10B_3 | 0.9900 | O1_11—H1_11 | 0.8400 |
C11_3—C12_3 | 1.525 (5) | O2_11—C17_11 | 1.232 (4) |
C11_3—H11A_3 | 0.9900 | O3_11—C19_11 | 1.363 (4) |
C11_3—H11B_3 | 0.9900 | O3_11—H3_11 | 0.8400 |
C12_3—H12A_3 | 0.9800 | O4_11—C23_11 | 1.355 (3) |
C12_3—H12B_3 | 0.9800 | O4_11—H4_11 | 0.8400 |
C12_3—H12C_3 | 0.9800 | C17_11—C18_11 | 1.467 (4) |
C13_3—C14_3 | 1.518 (5) | C18_11—C19_11 | 1.411 (4) |
C13_3—H13A_3 | 0.9900 | C18_11—C23_11 | 1.419 (4) |
C13_3—H13B_3 | 0.9900 | C19_11—C20_11 | 1.382 (4) |
C14_3—C15_3 | 1.526 (5) | C20_11—C21_11 | 1.375 (4) |
C14_3—H14A_3 | 0.9900 | C20_11—H20_11 | 0.9500 |
C14_3—H14B_3 | 0.9900 | C21_11—C22_11 | 1.378 (4) |
C15_3—C16_3 | 1.511 (6) | C21_11—H21_11 | 0.9500 |
C15_3—H15A_3 | 0.9900 | C22_11—C23_11 | 1.377 (4) |
C15_3—H15B_3 | 0.9900 | C22_11—H22_11 | 0.9500 |
C16_3—H16A_3 | 0.9800 | O1_12—C17_12 | 1.321 (4) |
C16_3—H16B_3 | 0.9800 | O1_12—H1_12 | 0.8400 |
C16_3—H16C_3 | 0.9800 | O2_12—C17_12 | 1.229 (4) |
N1_4—C9_4 | 1.514 (4) | O3_12—C19_12 | 1.363 (4) |
N1_4—C5_4 | 1.523 (4) | O3_12—H3_12 | 0.8400 |
N1_4—C1_4 | 1.527 (4) | O4_12—C23_12 | 1.352 (4) |
N1_4—C13_4 | 1.528 (4) | O4_12—H4_12 | 0.8400 |
C1_4—C2_4 | 1.514 (5) | C17_12—C18_12 | 1.463 (4) |
C1_4—H1A_4 | 0.9900 | C18_12—C19_12 | 1.397 (5) |
C1_4—H1B_4 | 0.9900 | C18_12—C23_12 | 1.421 (4) |
C2_4—C3_4 | 1.523 (5) | C19_12—C20_12 | 1.384 (4) |
C2_4—H2A_4 | 0.9900 | C20_12—C21_12 | 1.393 (4) |
C2_4—H2B_4 | 0.9900 | C20_12—H20_12 | 0.9500 |
C3_4—C4_4 | 1.504 (5) | C21_12—C22_12 | 1.373 (5) |
C3_4—H3A_4 | 0.9900 | C21_12—H21_12 | 0.9500 |
C3_4—H3B_4 | 0.9900 | C22_12—C23_12 | 1.389 (4) |
C4_4—H4A_4 | 0.9800 | C22_12—H22_12 | 0.9500 |
C5_1—N1_1—C9_1 | 111.2 (3) | C14_3—C15_3—H15B_3 | 109.1 |
C5_1—N1_1—C13_1 | 107.6 (2) | H15A_3—C15_3—H15B_3 | 107.8 |
C9_1—N1_1—C13_1 | 110.2 (2) | C15_3—C16_3—H16A_3 | 109.5 |
C5_1—N1_1—C1_1 | 111.3 (2) | C15_3—C16_3—H16B_3 | 109.5 |
C9_1—N1_1—C1_1 | 106.2 (2) | H16A_3—C16_3—H16B_3 | 109.5 |
C13_1—N1_1—C1_1 | 110.4 (2) | C15_3—C16_3—H16C_3 | 109.5 |
N1_1—C1_1—C2_1 | 114.8 (3) | H16A_3—C16_3—H16C_3 | 109.5 |
N1_1—C1_1—H1A_1 | 108.6 | H16B_3—C16_3—H16C_3 | 109.5 |
C2_1—C1_1—H1A_1 | 108.6 | C9_4—N1_4—C5_4 | 111.0 (2) |
N1_1—C1_1—H1B_1 | 108.6 | C9_4—N1_4—C1_4 | 106.6 (2) |
C2_1—C1_1—H1B_1 | 108.6 | C5_4—N1_4—C1_4 | 110.4 (2) |
H1A_1—C1_1—H1B_1 | 107.5 | C9_4—N1_4—C13_4 | 111.2 (2) |
C1_1—C2_1—C3_1 | 110.0 (3) | C5_4—N1_4—C13_4 | 106.2 (2) |
C1_1—C2_1—H2A_1 | 109.7 | C1_4—N1_4—C13_4 | 111.5 (2) |
C3_1—C2_1—H2A_1 | 109.7 | C2_4—C1_4—N1_4 | 116.1 (3) |
C1_1—C2_1—H2B_1 | 109.7 | C2_4—C1_4—H1A_4 | 108.3 |
C3_1—C2_1—H2B_1 | 109.7 | N1_4—C1_4—H1A_4 | 108.3 |
H2A_1—C2_1—H2B_1 | 108.2 | C2_4—C1_4—H1B_4 | 108.3 |
C4_1—C3_1—C2_1 | 111.8 (3) | N1_4—C1_4—H1B_4 | 108.3 |
C4_1—C3_1—H3A_1 | 109.3 | H1A_4—C1_4—H1B_4 | 107.4 |
C2_1—C3_1—H3A_1 | 109.3 | C1_4—C2_4—C3_4 | 110.6 (3) |
C4_1—C3_1—H3B_1 | 109.3 | C1_4—C2_4—H2A_4 | 109.5 |
C2_1—C3_1—H3B_1 | 109.3 | C3_4—C2_4—H2A_4 | 109.5 |
H3A_1—C3_1—H3B_1 | 107.9 | C1_4—C2_4—H2B_4 | 109.5 |
C3_1—C4_1—H4A_1 | 109.5 | C3_4—C2_4—H2B_4 | 109.5 |
C3_1—C4_1—H4B_1 | 109.5 | H2A_4—C2_4—H2B_4 | 108.1 |
H4A_1—C4_1—H4B_1 | 109.5 | C4_4—C3_4—C2_4 | 113.0 (3) |
C3_1—C4_1—H4C_1 | 109.5 | C4_4—C3_4—H3A_4 | 109.0 |
H4A_1—C4_1—H4C_1 | 109.5 | C2_4—C3_4—H3A_4 | 109.0 |
H4B_1—C4_1—H4C_1 | 109.5 | C4_4—C3_4—H3B_4 | 109.0 |
N1_1—C5_1—C6_1 | 114.7 (2) | C2_4—C3_4—H3B_4 | 109.0 |
N1_1—C5_1—H5A_1 | 108.6 | H3A_4—C3_4—H3B_4 | 107.8 |
C6_1—C5_1—H5A_1 | 108.6 | C3_4—C4_4—H4A_4 | 109.5 |
N1_1—C5_1—H5B_1 | 108.6 | C3_4—C4_4—H4B_4 | 109.5 |
C6_1—C5_1—H5B_1 | 108.6 | H4A_4—C4_4—H4B_4 | 109.5 |
H5A_1—C5_1—H5B_1 | 107.6 | C3_4—C4_4—H4C_4 | 109.5 |
C5_1—C6_1—C7_1 | 111.3 (3) | H4A_4—C4_4—H4C_4 | 109.5 |
C5_1—C6_1—H6A_1 | 109.4 | H4B_4—C4_4—H4C_4 | 109.5 |
C7_1—C6_1—H6A_1 | 109.4 | C6_4—C5_4—N1_4 | 116.4 (2) |
C5_1—C6_1—H6B_1 | 109.4 | C6_4—C5_4—H5A_4 | 108.2 |
C7_1—C6_1—H6B_1 | 109.4 | N1_4—C5_4—H5A_4 | 108.2 |
H6A_1—C6_1—H6B_1 | 108.0 | C6_4—C5_4—H5B_4 | 108.2 |
C8_1—C7_1—C6_1 | 110.7 (3) | N1_4—C5_4—H5B_4 | 108.2 |
C8_1—C7_1—H7A_1 | 109.5 | H5A_4—C5_4—H5B_4 | 107.3 |
C6_1—C7_1—H7A_1 | 109.5 | C5_4—C6_4—C7_4 | 108.2 (3) |
C8_1—C7_1—H7B_1 | 109.5 | C5_4—C6_4—H6A_4 | 110.1 |
C6_1—C7_1—H7B_1 | 109.5 | C7_4—C6_4—H6A_4 | 110.1 |
H7A_1—C7_1—H7B_1 | 108.1 | C5_4—C6_4—H6B_4 | 110.1 |
C7_1—C8_1—H8A_1 | 109.5 | C7_4—C6_4—H6B_4 | 110.1 |
C7_1—C8_1—H8B_1 | 109.5 | H6A_4—C6_4—H6B_4 | 108.4 |
H8A_1—C8_1—H8B_1 | 109.5 | C8_4—C7_4—C6_4 | 112.6 (3) |
C7_1—C8_1—H8C_1 | 109.5 | C8_4—C7_4—H7A_4 | 109.1 |
H8A_1—C8_1—H8C_1 | 109.5 | C6_4—C7_4—H7A_4 | 109.1 |
H8B_1—C8_1—H8C_1 | 109.5 | C8_4—C7_4—H7B_4 | 109.1 |
C10_1—C9_1—N1_1 | 115.9 (3) | C6_4—C7_4—H7B_4 | 109.1 |
C10_1—C9_1—H9A_1 | 108.3 | H7A_4—C7_4—H7B_4 | 107.8 |
N1_1—C9_1—H9A_1 | 108.3 | C7_4—C8_4—H8A_4 | 109.5 |
C10_1—C9_1—H9B_1 | 108.3 | C7_4—C8_4—H8B_4 | 109.5 |
N1_1—C9_1—H9B_1 | 108.3 | H8A_4—C8_4—H8B_4 | 109.5 |
H9A_1—C9_1—H9B_1 | 107.4 | C7_4—C8_4—H8C_4 | 109.5 |
C11_1—C10_1—C9_1 | 109.7 (3) | H8A_4—C8_4—H8C_4 | 109.5 |
C11_1—C10_1—H10A_1 | 109.7 | H8B_4—C8_4—H8C_4 | 109.5 |
C9_1—C10_1—H10A_1 | 109.7 | N1_4—C9_4—C10_4 | 117.4 (2) |
C11_1—C10_1—H10B_1 | 109.7 | N1_4—C9_4—H9A_4 | 108.0 |
C9_1—C10_1—H10B_1 | 109.7 | C10_4—C9_4—H9A_4 | 108.0 |
H10A_1—C10_1—H10B_1 | 108.2 | N1_4—C9_4—H9B_4 | 108.0 |
C10_1—C11_1—C12_1 | 113.8 (3) | C10_4—C9_4—H9B_4 | 108.0 |
C10_1—C11_1—H11A_1 | 108.8 | H9A_4—C9_4—H9B_4 | 107.2 |
C12_1—C11_1—H11A_1 | 108.8 | C9_4—C10_4—C11_4 | 109.1 (3) |
C10_1—C11_1—H11B_1 | 108.8 | C9_4—C10_4—H10A_4 | 109.9 |
C12_1—C11_1—H11B_1 | 108.8 | C11_4—C10_4—H10A_4 | 109.9 |
H11A_1—C11_1—H11B_1 | 107.7 | C9_4—C10_4—H10B_4 | 109.9 |
C11_1—C12_1—H12A_1 | 109.5 | C11_4—C10_4—H10B_4 | 109.9 |
C11_1—C12_1—H12B_1 | 109.5 | H10A_4—C10_4—H10B_4 | 108.3 |
H12A_1—C12_1—H12B_1 | 109.5 | C10_4—C11_4—C12_4 | 113.0 (3) |
C11_1—C12_1—H12C_1 | 109.5 | C10_4—C11_4—H11A_4 | 109.0 |
H12A_1—C12_1—H12C_1 | 109.5 | C12_4—C11_4—H11A_4 | 109.0 |
H12B_1—C12_1—H12C_1 | 109.5 | C10_4—C11_4—H11B_4 | 109.0 |
C14_1—C13_1—N1_1 | 115.7 (2) | C12_4—C11_4—H11B_4 | 109.0 |
C14_1—C13_1—H13A_1 | 108.4 | H11A_4—C11_4—H11B_4 | 107.8 |
N1_1—C13_1—H13A_1 | 108.4 | C11_4—C12_4—H12A_4 | 109.5 |
C14_1—C13_1—H13B_1 | 108.4 | C11_4—C12_4—H12B_4 | 109.5 |
N1_1—C13_1—H13B_1 | 108.3 | H12A_4—C12_4—H12B_4 | 109.5 |
H13A_1—C13_1—H13B_1 | 107.4 | C11_4—C12_4—H12C_4 | 109.5 |
C13_1—C14_1—C15_1 | 110.9 (3) | H12A_4—C12_4—H12C_4 | 109.5 |
C13_1—C14_1—H14A_1 | 109.5 | H12B_4—C12_4—H12C_4 | 109.5 |
C15_1—C14_1—H14A_1 | 109.5 | C14_4—C13_4—N1_4 | 115.8 (3) |
C13_1—C14_1—H14B_1 | 109.5 | C14_4—C13_4—H13A_4 | 108.3 |
C15_1—C14_1—H14B_1 | 109.5 | N1_4—C13_4—H13A_4 | 108.3 |
H14A_1—C14_1—H14B_1 | 108.0 | C14_4—C13_4—H13B_4 | 108.3 |
C16_1—C15_1—C14_1 | 112.9 (3) | N1_4—C13_4—H13B_4 | 108.3 |
C16_1—C15_1—H15A_1 | 109.0 | H13A_4—C13_4—H13B_4 | 107.4 |
C14_1—C15_1—H15A_1 | 109.0 | C13_4—C14_4—C15_4 | 109.5 (3) |
C16_1—C15_1—H15B_1 | 109.0 | C13_4—C14_4—H14A_4 | 109.8 |
C14_1—C15_1—H15B_1 | 109.0 | C15_4—C14_4—H14A_4 | 109.8 |
H15A_1—C15_1—H15B_1 | 107.8 | C13_4—C14_4—H14B_4 | 109.8 |
C15_1—C16_1—H16A_1 | 109.5 | C15_4—C14_4—H14B_4 | 109.8 |
C15_1—C16_1—H16B_1 | 109.5 | H14A_4—C14_4—H14B_4 | 108.2 |
H16A_1—C16_1—H16B_1 | 109.5 | C16_4—C15_4—C14_4 | 111.5 (3) |
C15_1—C16_1—H16C_1 | 109.5 | C16_4—C15_4—H15A_4 | 109.3 |
H16A_1—C16_1—H16C_1 | 109.5 | C14_4—C15_4—H15A_4 | 109.3 |
H16B_1—C16_1—H16C_1 | 109.5 | C16_4—C15_4—H15B_4 | 109.3 |
C5_2—N1_2—C1_2 | 109.9 (2) | C14_4—C15_4—H15B_4 | 109.3 |
C5_2—N1_2—C9_2 | 110.7 (2) | H15A_4—C15_4—H15B_4 | 108.0 |
C1_2—N1_2—C9_2 | 107.8 (2) | C15_4—C16_4—H16A_4 | 109.5 |
C5_2—N1_2—C13_2 | 107.2 (2) | C15_4—C16_4—H16B_4 | 109.5 |
C1_2—N1_2—C13_2 | 110.6 (2) | H16A_4—C16_4—H16B_4 | 109.5 |
C9_2—N1_2—C13_2 | 110.6 (2) | C15_4—C16_4—H16C_4 | 109.5 |
C2_2—C1_2—N1_2 | 115.3 (3) | H16A_4—C16_4—H16C_4 | 109.5 |
C2_2—C1_2—H1A_2 | 108.5 | H16B_4—C16_4—H16C_4 | 109.5 |
N1_2—C1_2—H1A_2 | 108.5 | C19_5—O3_5—H3_5 | 109.5 |
C2_2—C1_2—H1B_2 | 108.5 | C23_5—O4_5—H4_5 | 109.5 |
N1_2—C1_2—H1B_2 | 108.5 | O1_5—C17_5—O2_5 | 122.7 (3) |
H1A_2—C1_2—H1B_2 | 107.5 | O1_5—C17_5—C18_5 | 120.2 (3) |
C3_2—C2_2—C1_2 | 112.4 (3) | O2_5—C17_5—C18_5 | 117.1 (3) |
C3_2—C2_2—H2A_2 | 109.1 | C19_5—C18_5—C23_5 | 118.2 (3) |
C1_2—C2_2—H2A_2 | 109.1 | C19_5—C18_5—C17_5 | 121.6 (3) |
C3_2—C2_2—H2B_2 | 109.1 | C23_5—C18_5—C17_5 | 120.2 (3) |
C1_2—C2_2—H2B_2 | 109.1 | O3_5—C19_5—C20_5 | 117.8 (3) |
H2A_2—C2_2—H2B_2 | 107.8 | O3_5—C19_5—C18_5 | 121.1 (3) |
C2_2—C3_2—C4_2 | 111.7 (3) | C20_5—C19_5—C18_5 | 121.1 (3) |
C2_2—C3_2—H3A_2 | 109.3 | C19_5—C20_5—C21_5 | 119.1 (3) |
C4_2—C3_2—H3A_2 | 109.3 | C19_5—C20_5—H20_5 | 120.4 |
C2_2—C3_2—H3B_2 | 109.3 | C21_5—C20_5—H20_5 | 120.4 |
C4_2—C3_2—H3B_2 | 109.3 | C22_5—C21_5—C20_5 | 121.5 (3) |
H3A_2—C3_2—H3B_2 | 107.9 | C22_5—C21_5—H21_5 | 119.2 |
C3_2—C4_2—H4A_2 | 109.5 | C20_5—C21_5—H21_5 | 119.2 |
C3_2—C4_2—H4B_2 | 109.5 | C21_5—C22_5—C23_5 | 119.6 (3) |
H4A_2—C4_2—H4B_2 | 109.5 | C21_5—C22_5—H22_5 | 120.2 |
C3_2—C4_2—H4C_2 | 109.5 | C23_5—C22_5—H22_5 | 120.2 |
H4A_2—C4_2—H4C_2 | 109.5 | O4_5—C23_5—C22_5 | 118.2 (3) |
H4B_2—C4_2—H4C_2 | 109.5 | O4_5—C23_5—C18_5 | 121.3 (2) |
C6_2—C5_2—N1_2 | 115.8 (3) | C22_5—C23_5—C18_5 | 120.4 (3) |
C6_2—C5_2—H5A_2 | 108.3 | C19_6—O3_6—H3_6 | 109.5 |
N1_2—C5_2—H5A_2 | 108.3 | C23_6—O4_6—H4_6 | 109.5 |
C6_2—C5_2—H5B_2 | 108.3 | O2_6—C17_6—O1_6 | 122.9 (3) |
N1_2—C5_2—H5B_2 | 108.3 | O2_6—C17_6—C18_6 | 120.3 (3) |
H5A_2—C5_2—H5B_2 | 107.4 | O1_6—C17_6—C18_6 | 116.8 (3) |
C5_2—C6_2—C7_2 | 110.2 (3) | C19_6—C18_6—C23_6 | 118.0 (3) |
C5_2—C6_2—H6A_2 | 109.6 | C19_6—C18_6—C17_6 | 120.1 (3) |
C7_2—C6_2—H6A_2 | 109.6 | C23_6—C18_6—C17_6 | 121.9 (3) |
C5_2—C6_2—H6B_2 | 109.6 | O3_6—C19_6—C20_6 | 118.5 (2) |
C7_2—C6_2—H6B_2 | 109.6 | O3_6—C19_6—C18_6 | 121.0 (3) |
H6A_2—C6_2—H6B_2 | 108.1 | C20_6—C19_6—C18_6 | 120.6 (3) |
C8_2—C7_2—C6_2 | 112.5 (3) | C21_6—C20_6—C19_6 | 119.3 (3) |
C8_2—C7_2—H7A_2 | 109.1 | C21_6—C20_6—H20_6 | 120.4 |
C6_2—C7_2—H7A_2 | 109.1 | C19_6—C20_6—H20_6 | 120.4 |
C8_2—C7_2—H7B_2 | 109.1 | C20_6—C21_6—C22_6 | 122.1 (3) |
C6_2—C7_2—H7B_2 | 109.1 | C20_6—C21_6—H21_6 | 119.0 |
H7A_2—C7_2—H7B_2 | 107.8 | C22_6—C21_6—H21_6 | 119.0 |
C7_2—C8_2—H8A_2 | 109.5 | C23_6—C22_6—C21_6 | 119.1 (3) |
C7_2—C8_2—H8B_2 | 109.5 | C23_6—C22_6—H22_6 | 120.4 |
H8A_2—C8_2—H8B_2 | 109.5 | C21_6—C22_6—H22_6 | 120.4 |
C7_2—C8_2—H8C_2 | 109.5 | O4_6—C23_6—C22_6 | 118.2 (3) |
H8A_2—C8_2—H8C_2 | 109.5 | O4_6—C23_6—C18_6 | 121.0 (3) |
H8B_2—C8_2—H8C_2 | 109.5 | C22_6—C23_6—C18_6 | 120.9 (3) |
C10_2—C9_2—N1_2 | 115.2 (2) | C19_7—O3_7—H3_7 | 109.5 |
C10_2—C9_2—H9A_2 | 108.5 | C23_7—O4_7—H4_7 | 109.5 |
N1_2—C9_2—H9A_2 | 108.5 | O2_7—C17_7—O1_7 | 122.6 (3) |
C10_2—C9_2—H9B_2 | 108.5 | O2_7—C17_7—C18_7 | 120.1 (3) |
N1_2—C9_2—H9B_2 | 108.5 | O1_7—C17_7—C18_7 | 117.3 (3) |
H9A_2—C9_2—H9B_2 | 107.5 | C19_7—C18_7—C23_7 | 117.8 (3) |
C9_2—C10_2—C11_2 | 110.4 (3) | C19_7—C18_7—C17_7 | 120.5 (3) |
C9_2—C10_2—H10A_2 | 109.6 | C23_7—C18_7—C17_7 | 121.7 (3) |
C11_2—C10_2—H10A_2 | 109.6 | O3_7—C19_7—C20_7 | 117.7 (3) |
C9_2—C10_2—H10B_2 | 109.6 | O3_7—C19_7—C18_7 | 121.1 (3) |
C11_2—C10_2—H10B_2 | 109.6 | C20_7—C19_7—C18_7 | 121.2 (3) |
H10A_2—C10_2—H10B_2 | 108.1 | C21_7—C20_7—C19_7 | 119.0 (3) |
C10_2—C11_2—C12_2 | 111.9 (3) | C21_7—C20_7—H20_7 | 120.5 |
C10_2—C11_2—H11A_2 | 109.2 | C19_7—C20_7—H20_7 | 120.5 |
C12_2—C11_2—H11A_2 | 109.2 | C20_7—C21_7—C22_7 | 121.7 (3) |
C10_2—C11_2—H11B_2 | 109.2 | C20_7—C21_7—H21_7 | 119.2 |
C12_2—C11_2—H11B_2 | 109.2 | C22_7—C21_7—H21_7 | 119.2 |
H11A_2—C11_2—H11B_2 | 107.9 | C21_7—C22_7—C23_7 | 119.6 (3) |
C11_2—C12_2—H12A_2 | 109.5 | C21_7—C22_7—H22_7 | 120.2 |
C11_2—C12_2—H12B_2 | 109.5 | C23_7—C22_7—H22_7 | 120.2 |
H12A_2—C12_2—H12B_2 | 109.5 | O4_7—C23_7—C22_7 | 117.9 (3) |
C11_2—C12_2—H12C_2 | 109.5 | O4_7—C23_7—C18_7 | 121.2 (3) |
H12A_2—C12_2—H12C_2 | 109.5 | C22_7—C23_7—C18_7 | 120.8 (3) |
H12B_2—C12_2—H12C_2 | 109.5 | C19_8—O3_8—H3_8 | 109.5 |
C14_2—C13_2—N1_2 | 114.5 (3) | C23_8—O4_8—H4_8 | 109.5 |
C14_2—C13_2—H13A_2 | 108.6 | O1_8—C17_8—O2_8 | 122.2 (3) |
N1_2—C13_2—H13A_2 | 108.6 | O1_8—C17_8—C18_8 | 120.8 (3) |
C14_2—C13_2—H13B_2 | 108.6 | O2_8—C17_8—C18_8 | 117.0 (3) |
N1_2—C13_2—H13B_2 | 108.6 | C19_8—C18_8—C23_8 | 117.8 (3) |
H13A_2—C13_2—H13B_2 | 107.6 | C19_8—C18_8—C17_8 | 122.1 (3) |
C13_2—C14_2—C15_2 | 111.0 (3) | C23_8—C18_8—C17_8 | 120.0 (2) |
C13_2—C14_2—H14A_2 | 109.4 | O3_8—C19_8—C20_8 | 118.1 (3) |
C15_2—C14_2—H14A_2 | 109.4 | O3_8—C19_8—C18_8 | 120.7 (3) |
C13_2—C14_2—H14B_2 | 109.4 | C20_8—C19_8—C18_8 | 121.2 (3) |
C15_2—C14_2—H14B_2 | 109.4 | C19_8—C20_8—C21_8 | 119.7 (3) |
H14A_2—C14_2—H14B_2 | 108.0 | C19_8—C20_8—H20_8 | 120.1 |
C14_2—C15_2—C16_2 | 110.4 (3) | C21_8—C20_8—H20_8 | 120.1 |
C14_2—C15_2—H15A_2 | 109.6 | C22_8—C21_8—C20_8 | 120.7 (3) |
C16_2—C15_2—H15A_2 | 109.6 | C22_8—C21_8—H21_8 | 119.7 |
C14_2—C15_2—H15B_2 | 109.6 | C20_8—C21_8—H21_8 | 119.7 |
C16_2—C15_2—H15B_2 | 109.6 | C21_8—C22_8—C23_8 | 119.8 (3) |
H15A_2—C15_2—H15B_2 | 108.1 | C21_8—C22_8—H22_8 | 120.1 |
C15_2—C16_2—H16A_2 | 109.5 | C23_8—C22_8—H22_8 | 120.1 |
C15_2—C16_2—H16B_2 | 109.5 | O4_8—C23_8—C22_8 | 118.0 (2) |
H16A_2—C16_2—H16B_2 | 109.5 | O4_8—C23_8—C18_8 | 121.2 (3) |
C15_2—C16_2—H16C_2 | 109.5 | C22_8—C23_8—C18_8 | 120.8 (3) |
H16A_2—C16_2—H16C_2 | 109.5 | C17_9—O1_9—H1_9 | 109.5 |
H16B_2—C16_2—H16C_2 | 109.5 | C19_9—O3_9—H3_9 | 109.5 |
C5_3—N1_3—C13_3 | 106.4 (2) | C23_9—O4_9—H4_9 | 109.5 |
C5_3—N1_3—C1_3 | 110.8 (2) | O2_9—C17_9—O1_9 | 117.5 (3) |
C13_3—N1_3—C1_3 | 110.3 (3) | O2_9—C17_9—C18_9 | 122.7 (3) |
C5_3—N1_3—C9_3 | 112.0 (3) | O1_9—C17_9—C18_9 | 119.8 (3) |
C13_3—N1_3—C9_3 | 110.4 (2) | C23_9—C18_9—C19_9 | 117.5 (3) |
C1_3—N1_3—C9_3 | 107.0 (2) | C23_9—C18_9—C17_9 | 123.6 (3) |
C2_3—C1_3—N1_3 | 115.3 (3) | C19_9—C18_9—C17_9 | 118.9 (3) |
C2_3—C1_3—H1A_3 | 108.4 | O3_9—C19_9—C20_9 | 117.7 (3) |
N1_3—C1_3—H1A_3 | 108.4 | O3_9—C19_9—C18_9 | 120.9 (3) |
C2_3—C1_3—H1B_3 | 108.4 | C20_9—C19_9—C18_9 | 121.5 (3) |
N1_3—C1_3—H1B_3 | 108.4 | C21_9—C20_9—C19_9 | 119.0 (3) |
H1A_3—C1_3—H1B_3 | 107.5 | C21_9—C20_9—H20_9 | 120.5 |
C1_3—C2_3—C3_3 | 111.6 (3) | C19_9—C20_9—H20_9 | 120.5 |
C1_3—C2_3—H2A_3 | 109.3 | C20_9—C21_9—C22_9 | 122.1 (3) |
C3_3—C2_3—H2A_3 | 109.3 | C20_9—C21_9—H21_9 | 118.9 |
C1_3—C2_3—H2B_3 | 109.3 | C22_9—C21_9—H21_9 | 118.9 |
C3_3—C2_3—H2B_3 | 109.3 | C23_9—C22_9—C21_9 | 118.6 (3) |
H2A_3—C2_3—H2B_3 | 108.0 | C23_9—C22_9—H22_9 | 120.7 |
C4_3—C3_3—C2_3 | 110.9 (3) | C21_9—C22_9—H22_9 | 120.7 |
C4_3—C3_3—H3A_3 | 109.5 | O4_9—C23_9—C22_9 | 121.6 (3) |
C2_3—C3_3—H3A_3 | 109.5 | O4_9—C23_9—C18_9 | 117.3 (3) |
C4_3—C3_3—H3B_3 | 109.5 | C22_9—C23_9—C18_9 | 121.2 (3) |
C2_3—C3_3—H3B_3 | 109.5 | C17_10—O1_10—H1_10 | 109.5 |
H3A_3—C3_3—H3B_3 | 108.1 | C19_10—O3_10—H3_10 | 109.5 |
C3_3—C4_3—H4A_3 | 109.5 | C23_10—O4_10—H4_10 | 109.5 |
C3_3—C4_3—H4B_3 | 109.5 | O2_10—C17_10—O1_10 | 117.7 (3) |
H4A_3—C4_3—H4B_3 | 109.5 | O2_10—C17_10—C18_10 | 122.0 (3) |
C3_3—C4_3—H4C_3 | 109.5 | O1_10—C17_10—C18_10 | 120.3 (3) |
H4A_3—C4_3—H4C_3 | 109.5 | C23_10—C18_10—C19_10 | 117.6 (3) |
H4B_3—C4_3—H4C_3 | 109.5 | C23_10—C18_10—C17_10 | 122.8 (3) |
N1_3—C5_3—C6_3 | 116.1 (3) | C19_10—C18_10—C17_10 | 119.5 (3) |
N1_3—C5_3—H5A_3 | 108.3 | O3_10—C19_10—C20_10 | 117.3 (3) |
C6_3—C5_3—H5A_3 | 108.3 | O3_10—C19_10—C18_10 | 121.4 (3) |
N1_3—C5_3—H5B_3 | 108.3 | C20_10—C19_10—C18_10 | 121.4 (3) |
C6_3—C5_3—H5B_3 | 108.3 | C21_10—C20_10—C19_10 | 119.4 (3) |
H5A_3—C5_3—H5B_3 | 107.4 | C21_10—C20_10—H20_10 | 120.3 |
C5_3—C6_3—C7_3 | 110.5 (3) | C19_10—C20_10—H20_10 | 120.3 |
C5_3—C6_3—H6A_3 | 109.5 | C20_10—C21_10—C22_10 | 121.3 (3) |
C7_3—C6_3—H6A_3 | 109.5 | C20_10—C21_10—H21_10 | 119.4 |
C5_3—C6_3—H6B_3 | 109.5 | C22_10—C21_10—H21_10 | 119.4 |
C7_3—C6_3—H6B_3 | 109.5 | C23_10—C22_10—C21_10 | 119.3 (3) |
H6A_3—C6_3—H6B_3 | 108.1 | C23_10—C22_10—H22_10 | 120.4 |
C8_3—C7_3—C6_3 | 112.2 (3) | C21_10—C22_10—H22_10 | 120.4 |
C8_3—C7_3—H7A_3 | 109.2 | O4_10—C23_10—C22_10 | 121.3 (3) |
C6_3—C7_3—H7A_3 | 109.2 | O4_10—C23_10—C18_10 | 117.6 (3) |
C8_3—C7_3—H7B_3 | 109.2 | C22_10—C23_10—C18_10 | 121.1 (3) |
C6_3—C7_3—H7B_3 | 109.2 | C17_11—O1_11—H1_11 | 109.5 |
H7A_3—C7_3—H7B_3 | 107.9 | C19_11—O3_11—H3_11 | 109.5 |
C7_3—C8_3—H8A_3 | 109.5 | C23_11—O4_11—H4_11 | 109.5 |
C7_3—C8_3—H8B_3 | 109.5 | O2_11—C17_11—O1_11 | 117.6 (3) |
H8A_3—C8_3—H8B_3 | 109.5 | O2_11—C17_11—C18_11 | 122.4 (3) |
C7_3—C8_3—H8C_3 | 109.5 | O1_11—C17_11—C18_11 | 120.0 (3) |
H8A_3—C8_3—H8C_3 | 109.5 | C19_11—C18_11—C23_11 | 117.6 (3) |
H8B_3—C8_3—H8C_3 | 109.5 | C19_11—C18_11—C17_11 | 123.6 (3) |
C10_3—C9_3—N1_3 | 115.4 (2) | C23_11—C18_11—C17_11 | 118.7 (3) |
C10_3—C9_3—H9A_3 | 108.4 | O3_11—C19_11—C20_11 | 122.0 (3) |
N1_3—C9_3—H9A_3 | 108.4 | O3_11—C19_11—C18_11 | 117.1 (2) |
C10_3—C9_3—H9B_3 | 108.4 | C20_11—C19_11—C18_11 | 120.9 (3) |
N1_3—C9_3—H9B_3 | 108.4 | C21_11—C20_11—C19_11 | 119.4 (3) |
H9A_3—C9_3—H9B_3 | 107.5 | C21_11—C20_11—H20_11 | 120.3 |
C9_3—C10_3—C11_3 | 109.9 (3) | C19_11—C20_11—H20_11 | 120.3 |
C9_3—C10_3—H10A_3 | 109.7 | C20_11—C21_11—C22_11 | 121.7 (3) |
C11_3—C10_3—H10A_3 | 109.7 | C20_11—C21_11—H21_11 | 119.1 |
C9_3—C10_3—H10B_3 | 109.7 | C22_11—C21_11—H21_11 | 119.1 |
C11_3—C10_3—H10B_3 | 109.7 | C23_11—C22_11—C21_11 | 119.6 (3) |
H10A_3—C10_3—H10B_3 | 108.2 | C23_11—C22_11—H22_11 | 120.2 |
C12_3—C11_3—C10_3 | 111.5 (3) | C21_11—C22_11—H22_11 | 120.2 |
C12_3—C11_3—H11A_3 | 109.3 | O4_11—C23_11—C22_11 | 117.9 (3) |
C10_3—C11_3—H11A_3 | 109.3 | O4_11—C23_11—C18_11 | 121.4 (3) |
C12_3—C11_3—H11B_3 | 109.3 | C22_11—C23_11—C18_11 | 120.7 (3) |
C10_3—C11_3—H11B_3 | 109.3 | C17_12—O1_12—H1_12 | 109.5 |
H11A_3—C11_3—H11B_3 | 108.0 | C19_12—O3_12—H3_12 | 109.5 |
C11_3—C12_3—H12A_3 | 109.5 | C23_12—O4_12—H4_12 | 109.5 |
C11_3—C12_3—H12B_3 | 109.5 | O2_12—C17_12—O1_12 | 117.9 (3) |
H12A_3—C12_3—H12B_3 | 109.5 | O2_12—C17_12—C18_12 | 122.6 (3) |
C11_3—C12_3—H12C_3 | 109.5 | O1_12—C17_12—C18_12 | 119.6 (3) |
H12A_3—C12_3—H12C_3 | 109.5 | C19_12—C18_12—C23_12 | 117.9 (3) |
H12B_3—C12_3—H12C_3 | 109.5 | C19_12—C18_12—C17_12 | 123.5 (3) |
C14_3—C13_3—N1_3 | 116.3 (2) | C23_12—C18_12—C17_12 | 118.6 (3) |
C14_3—C13_3—H13A_3 | 108.2 | O3_12—C19_12—C20_12 | 120.5 (3) |
N1_3—C13_3—H13A_3 | 108.2 | O3_12—C19_12—C18_12 | 117.8 (2) |
C14_3—C13_3—H13B_3 | 108.2 | C20_12—C19_12—C18_12 | 121.7 (3) |
N1_3—C13_3—H13B_3 | 108.2 | C19_12—C20_12—C21_12 | 118.7 (3) |
H13A_3—C13_3—H13B_3 | 107.4 | C19_12—C20_12—H20_12 | 120.7 |
C13_3—C14_3—C15_3 | 108.9 (3) | C21_12—C20_12—H20_12 | 120.7 |
C13_3—C14_3—H14A_3 | 109.9 | C22_12—C21_12—C20_12 | 121.8 (3) |
C15_3—C14_3—H14A_3 | 109.9 | C22_12—C21_12—H21_12 | 119.1 |
C13_3—C14_3—H14B_3 | 109.9 | C20_12—C21_12—H21_12 | 119.1 |
C15_3—C14_3—H14B_3 | 109.9 | C21_12—C22_12—C23_12 | 119.5 (3) |
H14A_3—C14_3—H14B_3 | 108.3 | C21_12—C22_12—H22_12 | 120.3 |
C16_3—C15_3—C14_3 | 112.6 (3) | C23_12—C22_12—H22_12 | 120.3 |
C16_3—C15_3—H15A_3 | 109.1 | O4_12—C23_12—C22_12 | 117.9 (3) |
C14_3—C15_3—H15A_3 | 109.1 | O4_12—C23_12—C18_12 | 121.6 (3) |
C16_3—C15_3—H15B_3 | 109.1 | C22_12—C23_12—C18_12 | 120.5 (3) |
C5_1—N1_1—C1_1—C2_1 | −56.4 (4) | C19_6—C18_6—C23_6—O4_6 | 179.8 (3) |
C9_1—N1_1—C1_1—C2_1 | −177.5 (3) | C17_6—C18_6—C23_6—O4_6 | −1.2 (4) |
C13_1—N1_1—C1_1—C2_1 | 63.1 (4) | C19_6—C18_6—C23_6—C22_6 | 1.2 (4) |
N1_1—C1_1—C2_1—C3_1 | −177.7 (3) | C17_6—C18_6—C23_6—C22_6 | −179.8 (3) |
C1_1—C2_1—C3_1—C4_1 | −178.4 (3) | O2_7—C17_7—C18_7—C19_7 | −3.1 (4) |
C9_1—N1_1—C5_1—C6_1 | 58.3 (3) | O1_7—C17_7—C18_7—C19_7 | 177.1 (3) |
C13_1—N1_1—C5_1—C6_1 | 179.1 (3) | O2_7—C17_7—C18_7—C23_7 | 177.5 (3) |
C1_1—N1_1—C5_1—C6_1 | −59.9 (3) | O1_7—C17_7—C18_7—C23_7 | −2.2 (4) |
N1_1—C5_1—C6_1—C7_1 | −179.6 (3) | C23_7—C18_7—C19_7—O3_7 | 178.2 (3) |
C5_1—C6_1—C7_1—C8_1 | 176.9 (3) | C17_7—C18_7—C19_7—O3_7 | −1.2 (4) |
C5_1—N1_1—C9_1—C10_1 | 56.8 (3) | C23_7—C18_7—C19_7—C20_7 | −0.2 (4) |
C13_1—N1_1—C9_1—C10_1 | −62.5 (4) | C17_7—C18_7—C19_7—C20_7 | −179.6 (3) |
C1_1—N1_1—C9_1—C10_1 | 178.0 (3) | O3_7—C19_7—C20_7—C21_7 | −178.8 (3) |
N1_1—C9_1—C10_1—C11_1 | 179.4 (3) | C18_7—C19_7—C20_7—C21_7 | −0.3 (5) |
C9_1—C10_1—C11_1—C12_1 | −177.7 (3) | C19_7—C20_7—C21_7—C22_7 | 1.1 (5) |
C5_1—N1_1—C13_1—C14_1 | 176.1 (3) | C20_7—C21_7—C22_7—C23_7 | −1.3 (5) |
C9_1—N1_1—C13_1—C14_1 | −62.4 (3) | C21_7—C22_7—C23_7—O4_7 | −178.8 (3) |
C1_1—N1_1—C13_1—C14_1 | 54.5 (3) | C21_7—C22_7—C23_7—C18_7 | 0.7 (5) |
N1_1—C13_1—C14_1—C15_1 | 166.3 (3) | C19_7—C18_7—C23_7—O4_7 | 179.5 (3) |
C13_1—C14_1—C15_1—C16_1 | 174.5 (3) | C17_7—C18_7—C23_7—O4_7 | −1.1 (4) |
C5_2—N1_2—C1_2—C2_2 | −59.0 (3) | C19_7—C18_7—C23_7—C22_7 | 0.0 (4) |
C9_2—N1_2—C1_2—C2_2 | −179.8 (3) | C17_7—C18_7—C23_7—C22_7 | 179.4 (3) |
C13_2—N1_2—C1_2—C2_2 | 59.2 (4) | O1_8—C17_8—C18_8—C19_8 | 179.7 (3) |
N1_2—C1_2—C2_2—C3_2 | −178.3 (3) | O2_8—C17_8—C18_8—C19_8 | 0.1 (4) |
C1_2—C2_2—C3_2—C4_2 | −178.8 (3) | O1_8—C17_8—C18_8—C23_8 | 2.2 (4) |
C1_2—N1_2—C5_2—C6_2 | −63.2 (3) | O2_8—C17_8—C18_8—C23_8 | −177.4 (3) |
C9_2—N1_2—C5_2—C6_2 | 55.8 (4) | C23_8—C18_8—C19_8—O3_8 | 179.5 (3) |
C13_2—N1_2—C5_2—C6_2 | 176.5 (3) | C17_8—C18_8—C19_8—O3_8 | 2.0 (4) |
N1_2—C5_2—C6_2—C7_2 | 168.2 (3) | C23_8—C18_8—C19_8—C20_8 | −1.1 (4) |
C5_2—C6_2—C7_2—C8_2 | 175.1 (3) | C17_8—C18_8—C19_8—C20_8 | −178.6 (3) |
C5_2—N1_2—C9_2—C10_2 | 63.9 (3) | O3_8—C19_8—C20_8—C21_8 | 179.6 (3) |
C1_2—N1_2—C9_2—C10_2 | −175.8 (2) | C18_8—C19_8—C20_8—C21_8 | 0.2 (5) |
C13_2—N1_2—C9_2—C10_2 | −54.7 (3) | C19_8—C20_8—C21_8—C22_8 | −0.1 (5) |
N1_2—C9_2—C10_2—C11_2 | −169.5 (3) | C20_8—C21_8—C22_8—C23_8 | 0.9 (5) |
C9_2—C10_2—C11_2—C12_2 | −176.0 (3) | C21_8—C22_8—C23_8—O4_8 | 178.0 (3) |
C5_2—N1_2—C13_2—C14_2 | 176.1 (3) | C21_8—C22_8—C23_8—C18_8 | −1.8 (4) |
C1_2—N1_2—C13_2—C14_2 | 56.3 (4) | C19_8—C18_8—C23_8—O4_8 | −177.9 (3) |
C9_2—N1_2—C13_2—C14_2 | −63.1 (3) | C17_8—C18_8—C23_8—O4_8 | −0.3 (4) |
N1_2—C13_2—C14_2—C15_2 | 176.4 (3) | C19_8—C18_8—C23_8—C22_8 | 1.8 (4) |
C13_2—C14_2—C15_2—C16_2 | 178.4 (3) | C17_8—C18_8—C23_8—C22_8 | 179.5 (3) |
C5_3—N1_3—C1_3—C2_3 | −55.3 (4) | O2_9—C17_9—C18_9—C23_9 | 176.8 (3) |
C13_3—N1_3—C1_3—C2_3 | 62.2 (4) | O1_9—C17_9—C18_9—C23_9 | −3.2 (5) |
C9_3—N1_3—C1_3—C2_3 | −177.7 (3) | O2_9—C17_9—C18_9—C19_9 | −2.6 (5) |
N1_3—C1_3—C2_3—C3_3 | −175.7 (3) | O1_9—C17_9—C18_9—C19_9 | 177.4 (3) |
C1_3—C2_3—C3_3—C4_3 | −176.6 (4) | C23_9—C18_9—C19_9—O3_9 | −179.9 (3) |
C13_3—N1_3—C5_3—C6_3 | −179.8 (3) | C17_9—C18_9—C19_9—O3_9 | −0.5 (4) |
C1_3—N1_3—C5_3—C6_3 | −59.9 (4) | C23_9—C18_9—C19_9—C20_9 | 0.9 (4) |
C9_3—N1_3—C5_3—C6_3 | 59.6 (3) | C17_9—C18_9—C19_9—C20_9 | −179.7 (3) |
N1_3—C5_3—C6_3—C7_3 | 178.1 (3) | O3_9—C19_9—C20_9—C21_9 | −178.7 (3) |
C5_3—C6_3—C7_3—C8_3 | 179.0 (3) | C18_9—C19_9—C20_9—C21_9 | 0.6 (4) |
C5_3—N1_3—C9_3—C10_3 | 61.8 (3) | C19_9—C20_9—C21_9—C22_9 | −0.3 (5) |
C13_3—N1_3—C9_3—C10_3 | −56.6 (4) | C20_9—C21_9—C22_9—C23_9 | −1.4 (5) |
C1_3—N1_3—C9_3—C10_3 | −176.6 (3) | C21_9—C22_9—C23_9—O4_9 | −176.8 (3) |
N1_3—C9_3—C10_3—C11_3 | −171.4 (3) | C21_9—C22_9—C23_9—C18_9 | 2.8 (5) |
C9_3—C10_3—C11_3—C12_3 | −173.7 (3) | C19_9—C18_9—C23_9—O4_9 | 177.1 (3) |
C5_3—N1_3—C13_3—C14_3 | 177.5 (3) | C17_9—C18_9—C23_9—O4_9 | −2.3 (4) |
C1_3—N1_3—C13_3—C14_3 | 57.3 (3) | C19_9—C18_9—C23_9—C22_9 | −2.6 (4) |
C9_3—N1_3—C13_3—C14_3 | −60.8 (4) | C17_9—C18_9—C23_9—C22_9 | 178.0 (3) |
N1_3—C13_3—C14_3—C15_3 | 177.1 (3) | O2_10—C17_10—C18_10—C23_10 | −177.4 (3) |
C13_3—C14_3—C15_3—C16_3 | 176.7 (3) | O1_10—C17_10—C18_10—C23_10 | 3.5 (5) |
C9_4—N1_4—C1_4—C2_4 | −178.1 (3) | O2_10—C17_10—C18_10—C19_10 | 3.4 (5) |
C5_4—N1_4—C1_4—C2_4 | −57.4 (3) | O1_10—C17_10—C18_10—C19_10 | −175.8 (3) |
C13_4—N1_4—C1_4—C2_4 | 60.4 (3) | C23_10—C18_10—C19_10—O3_10 | −179.0 (3) |
N1_4—C1_4—C2_4—C3_4 | 179.3 (3) | C17_10—C18_10—C19_10—O3_10 | 0.4 (4) |
C1_4—C2_4—C3_4—C4_4 | −178.7 (3) | C23_10—C18_10—C19_10—C20_10 | 0.6 (4) |
C9_4—N1_4—C5_4—C6_4 | 59.4 (4) | C17_10—C18_10—C19_10—C20_10 | 179.9 (3) |
C1_4—N1_4—C5_4—C6_4 | −58.6 (3) | O3_10—C19_10—C20_10—C21_10 | 178.6 (3) |
C13_4—N1_4—C5_4—C6_4 | −179.6 (3) | C18_10—C19_10—C20_10—C21_10 | −1.0 (5) |
N1_4—C5_4—C6_4—C7_4 | −177.1 (3) | C19_10—C20_10—C21_10—C22_10 | −0.1 (5) |
C5_4—C6_4—C7_4—C8_4 | 179.6 (3) | C20_10—C21_10—C22_10—C23_10 | 1.4 (5) |
C5_4—N1_4—C9_4—C10_4 | 58.4 (3) | C21_10—C22_10—C23_10—O4_10 | 177.5 (3) |
C1_4—N1_4—C9_4—C10_4 | 178.7 (3) | C21_10—C22_10—C23_10—C18_10 | −1.8 (5) |
C13_4—N1_4—C9_4—C10_4 | −59.6 (3) | C19_10—C18_10—C23_10—O4_10 | −178.5 (3) |
N1_4—C9_4—C10_4—C11_4 | −179.8 (3) | C17_10—C18_10—C23_10—O4_10 | 2.2 (4) |
C9_4—C10_4—C11_4—C12_4 | −177.8 (3) | C19_10—C18_10—C23_10—C22_10 | 0.8 (5) |
C9_4—N1_4—C13_4—C14_4 | −61.8 (4) | C17_10—C18_10—C23_10—C22_10 | −178.5 (3) |
C5_4—N1_4—C13_4—C14_4 | 177.3 (3) | O2_11—C17_11—C18_11—C19_11 | 175.6 (3) |
C1_4—N1_4—C13_4—C14_4 | 57.1 (4) | O1_11—C17_11—C18_11—C19_11 | −5.0 (5) |
N1_4—C13_4—C14_4—C15_4 | 174.8 (3) | O2_11—C17_11—C18_11—C23_11 | −2.9 (5) |
C13_4—C14_4—C15_4—C16_4 | 176.7 (3) | O1_11—C17_11—C18_11—C23_11 | 176.4 (3) |
O1_5—C17_5—C18_5—C19_5 | −179.6 (3) | C23_11—C18_11—C19_11—O3_11 | 177.9 (3) |
O2_5—C17_5—C18_5—C19_5 | 0.3 (4) | C17_11—C18_11—C19_11—O3_11 | −0.7 (4) |
O1_5—C17_5—C18_5—C23_5 | 2.0 (4) | C23_11—C18_11—C19_11—C20_11 | −1.9 (4) |
O2_5—C17_5—C18_5—C23_5 | −178.0 (2) | C17_11—C18_11—C19_11—C20_11 | 179.5 (3) |
C23_5—C18_5—C19_5—O3_5 | 180.0 (3) | O3_11—C19_11—C20_11—C21_11 | −177.5 (3) |
C17_5—C18_5—C19_5—O3_5 | 1.6 (4) | C18_11—C19_11—C20_11—C21_11 | 2.3 (5) |
C23_5—C18_5—C19_5—C20_5 | −1.3 (4) | C19_11—C20_11—C21_11—C22_11 | −1.3 (5) |
C17_5—C18_5—C19_5—C20_5 | −179.7 (3) | C20_11—C21_11—C22_11—C23_11 | 0.1 (5) |
O3_5—C19_5—C20_5—C21_5 | 179.0 (3) | C21_11—C22_11—C23_11—O4_11 | −179.2 (3) |
C18_5—C19_5—C20_5—C21_5 | 0.3 (5) | C21_11—C22_11—C23_11—C18_11 | 0.3 (5) |
C19_5—C20_5—C21_5—C22_5 | 0.2 (5) | C19_11—C18_11—C23_11—O4_11 | −179.9 (3) |
C20_5—C21_5—C22_5—C23_5 | 0.4 (5) | C17_11—C18_11—C23_11—O4_11 | −1.3 (4) |
C21_5—C22_5—C23_5—O4_5 | 178.3 (3) | C19_11—C18_11—C23_11—C22_11 | 0.6 (4) |
C21_5—C22_5—C23_5—C18_5 | −1.4 (4) | C17_11—C18_11—C23_11—C22_11 | 179.3 (3) |
C19_5—C18_5—C23_5—O4_5 | −177.8 (3) | O2_12—C17_12—C18_12—C19_12 | −176.1 (3) |
C17_5—C18_5—C23_5—O4_5 | 0.6 (4) | O1_12—C17_12—C18_12—C19_12 | 4.1 (5) |
C19_5—C18_5—C23_5—C22_5 | 1.9 (4) | O2_12—C17_12—C18_12—C23_12 | 3.5 (5) |
C17_5—C18_5—C23_5—C22_5 | −179.7 (3) | O1_12—C17_12—C18_12—C23_12 | −176.3 (3) |
O2_6—C17_6—C18_6—C19_6 | −1.2 (4) | C23_12—C18_12—C19_12—O3_12 | −176.7 (3) |
O1_6—C17_6—C18_6—C19_6 | 179.1 (3) | C17_12—C18_12—C19_12—O3_12 | 2.9 (5) |
O2_6—C17_6—C18_6—C23_6 | 179.8 (3) | C23_12—C18_12—C19_12—C20_12 | 1.9 (5) |
O1_6—C17_6—C18_6—C23_6 | 0.1 (4) | C17_12—C18_12—C19_12—C20_12 | −178.4 (3) |
C23_6—C18_6—C19_6—O3_6 | 177.6 (3) | O3_12—C19_12—C20_12—C21_12 | 177.1 (3) |
C17_6—C18_6—C19_6—O3_6 | −1.5 (4) | C18_12—C19_12—C20_12—C21_12 | −1.5 (5) |
C23_6—C18_6—C19_6—C20_6 | −2.2 (4) | C19_12—C20_12—C21_12—C22_12 | −0.7 (5) |
C17_6—C18_6—C19_6—C20_6 | 178.8 (3) | C20_12—C21_12—C22_12—C23_12 | 2.2 (5) |
O3_6—C19_6—C20_6—C21_6 | −178.2 (3) | C21_12—C22_12—C23_12—O4_12 | 178.2 (3) |
C18_6—C19_6—C20_6—C21_6 | 1.6 (4) | C21_12—C22_12—C23_12—C18_12 | −1.6 (4) |
C19_6—C20_6—C21_6—C22_6 | 0.2 (5) | C19_12—C18_12—C23_12—O4_12 | 179.8 (3) |
C20_6—C21_6—C22_6—C23_6 | −1.3 (5) | C17_12—C18_12—C23_12—O4_12 | 0.2 (4) |
C21_6—C22_6—C23_6—O4_6 | −178.2 (3) | C19_12—C18_12—C23_12—C22_12 | −0.4 (4) |
C21_6—C22_6—C23_6—C18_6 | 0.5 (5) | C17_12—C18_12—C23_12—C22_12 | 180.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3_5—H3_5···O2_5 | 0.84 | 1.78 | 2.521 (3) | 147 |
O4_5—H4_5···O1_5 | 0.84 | 1.81 | 2.551 (3) | 146 |
O3_6—H3_6···O2_6 | 0.84 | 1.78 | 2.535 (3) | 148 |
O4_6—H4_6···O1_6 | 0.84 | 1.78 | 2.525 (3) | 148 |
O3_7—H3_7···O2_7 | 0.84 | 1.80 | 2.551 (3) | 147 |
O4_7—H4_7···O1_7 | 0.84 | 1.79 | 2.537 (3) | 147 |
O3_8—H3_8···O2_8 | 0.84 | 1.77 | 2.525 (3) | 148 |
O4_8—H4_8···O1_8 | 0.84 | 1.81 | 2.555 (3) | 148 |
O1_9—H1_9···O4_9 | 0.84 | 1.83 | 2.561 (3) | 145 |
O3_9—H3_9···O2_9 | 0.84 | 1.79 | 2.541 (3) | 148 |
O4_9—H4_9···O2_8 | 0.84 | 1.70 | 2.534 (3) | 174 |
O1_10—H1_10···O4_10 | 0.84 | 1.80 | 2.545 (3) | 146 |
O3_10—H3_10···O2_10 | 0.84 | 1.81 | 2.552 (3) | 147 |
O4_10—H4_10···O1_7i | 0.84 | 1.67 | 2.508 (3) | 175 |
O1_11—H1_11···O3_11 | 0.84 | 1.80 | 2.558 (3) | 149 |
O3_11—H3_11···O2_5ii | 0.84 | 1.71 | 2.542 (3) | 173 |
O4_11—H4_11···O2_11 | 0.84 | 1.80 | 2.544 (3) | 147 |
O1_12—H1_12···O3_12 | 0.84 | 1.79 | 2.545 (3) | 149 |
O3_12—H3_12···O1_6 | 0.84 | 1.69 | 2.521 (3) | 170 |
O4_12—H4_12···O2_12 | 0.84 | 1.80 | 2.547 (3) | 147 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H36N+·C7H5O4−·C7H6O4 |
Mr | 549.69 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 180 |
a, b, c (Å) | 13.9840 (3), 14.0507 (2), 15.4152 (4) |
α, β, γ (°) | 86.201 (6), 84.847 (7), 89.898 (7) |
V (Å3) | 3009.96 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.770, 0.806 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26943, 17008, 14232 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.113, 1.12 |
No. of reflections | 17008 |
No. of parameters | 1441 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: COLLECT (Nonius 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR92 (Altomare at al., 1994), SHELXTL (Bruker, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O3_5—H3_5···O2_5 | 0.84 | 1.78 | 2.521 (3) | 147 |
O4_5—H4_5···O1_5 | 0.84 | 1.81 | 2.551 (3) | 146 |
O3_6—H3_6···O2_6 | 0.84 | 1.78 | 2.535 (3) | 148 |
O4_6—H4_6···O1_6 | 0.84 | 1.78 | 2.525 (3) | 148 |
O3_7—H3_7···O2_7 | 0.84 | 1.80 | 2.551 (3) | 147 |
O4_7—H4_7···O1_7 | 0.84 | 1.79 | 2.537 (3) | 147 |
O3_8—H3_8···O2_8 | 0.84 | 1.77 | 2.525 (3) | 148 |
O4_8—H4_8···O1_8 | 0.84 | 1.81 | 2.555 (3) | 148 |
O1_9—H1_9···O4_9 | 0.84 | 1.83 | 2.561 (3) | 145 |
O3_9—H3_9···O2_9 | 0.84 | 1.79 | 2.541 (3) | 148 |
O4_9—H4_9···O2_8 | 0.84 | 1.70 | 2.534 (3) | 174 |
O1_10—H1_10···O4_10 | 0.84 | 1.80 | 2.545 (3) | 146 |
O3_10—H3_10···O2_10 | 0.84 | 1.81 | 2.552 (3) | 147 |
O4_10—H4_10···O1_7i | 0.84 | 1.67 | 2.508 (3) | 175 |
O1_11—H1_11···O3_11 | 0.84 | 1.80 | 2.558 (3) | 149 |
O3_11—H3_11···O2_5ii | 0.84 | 1.71 | 2.542 (3) | 173 |
O4_11—H4_11···O2_11 | 0.84 | 1.80 | 2.544 (3) | 147 |
O1_12—H1_12···O3_12 | 0.84 | 1.79 | 2.545 (3) | 149 |
O3_12—H3_12···O1_6 | 0.84 | 1.69 | 2.521 (3) | 170 |
O4_12—H4_12···O2_12 | 0.84 | 1.80 | 2.547 (3) | 147 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y+1, z. |
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The synthesis of lanthanide complexes with appropriate organic ligands which can act as light collectors in highly luminescent novel materials is of considerable interest (Soares-Santos, Nogueira, Felix et al., 2003). A literature survey shows that 2,6-dihydroxybenzoic acid (2,6-Hdhb) is an ideal candidate for such studies since it can coordinate to several metal centres in a variety of ways, viz. using only the carboxylate group, in either a monodentate or bidentate-chelating modes, or through the carboxylate group along with an adjacent hydroxyl in a salicylate-type chelate. Several complexes with d-transition metals [Cu2+ (Cariati et al., 1983), Co2+ (Erre et al., 1988), Re5+ (Bandoli et al., 1999), Pb2+ (Glowiak et al., 1992) and Mn2+ (Erre et al., 2000; Glowiak et al., 1995)] and lanthanide ions (Glowiak et al., 1999) have been reported. Several co-crystals of 2,6-Hdhb with other organic ligands have also been reported (Gdaniec et al., 1994; Lynch et al., 1994; Tarnura et al., 1973). We describe here a co-crystal of 2,6-Hdhb with tetrabutylammonium, (nBu4N)+, obtained in the course of our studies with lanthanide cations (Soares-Santos, Nogueira, Paz et al., 2003).
The title compound, (I), crystallizes in the P1 space group, with the unit cell containing 12 independent residues [four (nBu4N)+, four 2,6-Hdhb and another four 2,6-dhb−] (Fig. 1). (nBu4N)+ cations pack in the ab plane, forming a positively charged [nBu4N]nn+ layer which alternates in the c direction with a negatively charged layer, [(2,6-dhb)(2,6-Hdhb)]nn- (Fig. 2). The latter contains a hydrogen-bonding network formed by intramolecular bonds between the hydroxyl and the carboxylate groups from 2,6-dhb− and 2,6-Hdhb (Fig. 3). However, atom O1_b also acts as a bifurcated acceptor, establishing a hydrogen-bond bridge with the neighbouring O4_c atom (Fig. 3). A full listing of the hydrogen bonds is given in Table 1.