organic compounds
The asymmetric unit of the title compound, C6H21N43+·3C7H4NO4-·2H2O, consists of two triply protonated base molecules, six benzoate anions and four water molecules, one of which is unequally disordered across two adjacent sites in an extensive hydrogen-bonded network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015538/ob6271sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015538/ob6271Isup2.hkl |
CCDC reference: 221694
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- H-atom completeness 98%
- Disorder in solvent or counterion
- R factor = 0.059
- wR factor = 0.206
- Data-to-parameter ratio = 12.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
DIFMX_01 Alert C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.630 Test value = 0.600 DIFMX_02 Alert C The minimum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT_302 Alert C Anion/Solvent Disorder ......................... 20.00 Perc. PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C1H - C11H = 1.53 Ang. General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C27 H37 N7 O14 Atom count from the _atom_site data: C27 H36 N7 O14 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C27 H37 N7 O14 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 108.00 108.00 0.00 H 148.00 144.00 4.00 N 28.00 28.00 0.00 O 56.00 56.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
Computing details top
Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: Xtal3.2 (Hall et al., 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
Tris(2-ethylammonio)amine–4-nitrobenzoate–water (2/6/4) top
Crystal data top
C6H21N43+·3C7H4NO4−·2H2O | F(000) = 1440 |
Mr = 683.64 | Dx = 1.415 Mg m−3 |
Triclinic, P1 | Melting point: 457 K K |
a = 14.095 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.697 (1) Å | Cell parameters from 25 reflections |
c = 17.1308 (7) Å | θ = 6–14° |
α = 103.758 (5)° | µ = 0.12 mm−1 |
β = 99.715 (6)° | T = 298 K |
γ = 105.898 (7)° | Prism, yellow |
V = 3209.5 (3) Å3 | 0.60 × 0.50 × 0.50 mm |
Z = 4 |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 5646 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.011 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
2θ/ω scans | h = 0→16 |
Absorption correction: ψ scan (Xtal3.2; Hall et al., 1992) | k = −17→16 |
Tmin = 0.952, Tmax = 0.977 | l = −20→20 |
11786 measured reflections | 3 standard reflections every 200 reflections |
11286 independent reflections | intensity decay: 15% |
Refinement top
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.206 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1205P)2] where P = (Fo2 + 2Fc2)/3 |
11286 reflections | (Δ/σ)max < 0.001 |
922 parameters | Δρmax = 0.63 e Å−3 |
39 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.20585 (18) | 0.75547 (18) | 0.21820 (15) | 0.0403 (6) | |
C2A | 0.2579 (2) | 0.6844 (2) | 0.1893 (2) | 0.0482 (8) | |
H21A | 0.3201 | 0.6985 | 0.2310 | 0.060* | |
H22A | 0.2764 | 0.6928 | 0.1388 | 0.060* | |
C3A | 0.1919 (2) | 0.5779 (3) | 0.1726 (2) | 0.0544 (9) | |
H31A | 0.2290 | 0.5336 | 0.1543 | 0.068* | |
H32A | 0.1752 | 0.5683 | 0.2234 | 0.068* | |
N4A | 0.09676 (19) | 0.5538 (2) | 0.10802 (17) | 0.0513 (7) | |
H41A | 0.0585 | 0.5882 | 0.1278 | 0.064* | |
H42A | 0.0625 | 0.4892 | 0.0939 | 0.064* | |
H43A | 0.1122 | 0.5695 | 0.0636 | 0.064* | |
C5A | 0.2175 (3) | 0.7763 (3) | 0.30817 (19) | 0.0546 (9) | |
H51A | 0.2858 | 0.8213 | 0.3367 | 0.068* | |
H52A | 0.2101 | 0.7150 | 0.3223 | 0.068* | |
C6A | 0.1415 (3) | 0.8212 (3) | 0.3388 (2) | 0.0616 (10) | |
H61A | 0.1663 | 0.8535 | 0.3982 | 0.077* | |
H62A | 0.1350 | 0.8713 | 0.3122 | 0.077* | |
N7A | 0.0406 (2) | 0.7461 (3) | 0.3215 (2) | 0.0999 (14) | |
H71A | 0.0134 | 0.7229 | 0.2670 | 0.125* | |
H72A | 0.0002 | 0.7734 | 0.3463 | 0.125* | |
H73A | 0.0473 | 0.6964 | 0.3408 | 0.125* | |
C8A | 0.2465 (2) | 0.8483 (2) | 0.1990 (2) | 0.0493 (8) | |
H81A | 0.3203 | 0.8705 | 0.2165 | 0.062* | |
H82A | 0.2236 | 0.8985 | 0.2307 | 0.062* | |
C9A | 0.2145 (2) | 0.8391 (3) | 0.1080 (2) | 0.0512 (8) | |
H91A | 0.2434 | 0.9030 | 0.0998 | 0.064* | |
H92A | 0.2418 | 0.7927 | 0.0766 | 0.064* | |
N10A | 0.1020 (2) | 0.8045 (2) | 0.07568 (17) | 0.0532 (7) | |
H11A | 0.0759 | 0.8433 | 0.1075 | 0.066* | |
H12A | 0.0760 | 0.7423 | 0.0763 | 0.066* | |
H13A | 0.0867 | 0.8073 | 0.0239 | 0.066* | |
C1B | 0.7857 (2) | 0.3714 (2) | 0.12857 (19) | 0.0437 (8) | |
C11B | 0.8880 (3) | 0.3879 (3) | 0.1080 (2) | 0.0525 (9) | |
O10B | 0.9646 (2) | 0.4049 (2) | 0.16535 (18) | 0.0816 (9) | |
O11B | 0.8914 (2) | 0.3834 (2) | 0.03556 (16) | 0.0671 (7) | |
C2B | 0.7754 (3) | 0.3704 (2) | 0.2078 (2) | 0.0506 (8) | |
H2B | 0.8327 | 0.3818 | 0.2495 | 0.053 (9)* | |
C3B | 0.6809 (3) | 0.3528 (2) | 0.2254 (2) | 0.0563 (9) | |
H3B | 0.6735 | 0.3510 | 0.2780 | 0.060 (10)* | |
C4B | 0.5980 (3) | 0.3380 (3) | 0.1625 (2) | 0.0568 (9) | |
N41B | 0.4974 (3) | 0.3191 (3) | 0.1800 (3) | 0.0822 (11) | |
O41B | 0.4897 (3) | 0.3070 (3) | 0.2467 (3) | 0.1190 (13) | |
O42B | 0.4258 (3) | 0.3145 (3) | 0.1259 (3) | 0.1227 (14) | |
C5B | 0.6058 (3) | 0.3395 (3) | 0.0838 (2) | 0.0545 (9) | |
H5B | 0.5485 | 0.3293 | 0.0426 | 0.079 (12)* | |
C6B | 0.7000 (3) | 0.3564 (2) | 0.0677 (2) | 0.0505 (8) | |
H6B | 0.7065 | 0.3578 | 0.0148 | 0.070 (11)* | |
C1C | 0.7793 (2) | 0.6160 (2) | 0.1144 (2) | 0.0459 (8) | |
C11C | 0.8854 (3) | 0.6286 (3) | 0.1015 (3) | 0.0651 (10) | |
O10C | 0.8971 (3) | 0.6251 (3) | 0.0308 (3) | 0.1155 (13) | |
O11C | 0.9538 (2) | 0.6355 (3) | 0.1615 (2) | 0.1058 (12) | |
C2C | 0.7028 (3) | 0.6158 (3) | 0.0521 (2) | 0.0527 (9) | |
H2C | 0.7164 | 0.6231 | 0.0023 | 0.060 (10)* | |
C3C | 0.6070 (3) | 0.6048 (3) | 0.0636 (2) | 0.0542 (9) | |
H3C | 0.5558 | 0.6062 | 0.0223 | 0.083 (13)* | |
C4C | 0.5872 (2) | 0.5917 (2) | 0.1364 (2) | 0.0464 (8) | |
N41C | 0.4831 (2) | 0.5789 (3) | 0.1476 (2) | 0.0681 (9) | |
O41C | 0.4244 (2) | 0.5969 (3) | 0.0980 (2) | 0.1008 (11) | |
O42C | 0.4628 (2) | 0.5532 (3) | 0.2057 (2) | 0.1123 (12) | |
C5C | 0.6611 (2) | 0.5896 (2) | 0.1993 (2) | 0.0484 (8) | |
H5C | 0.6462 | 0.5795 | 0.2481 | 0.078 (12)* | |
C6C | 0.7581 (2) | 0.6031 (2) | 0.1875 (2) | 0.0476 (8) | |
H6C | 0.8098 | 0.6034 | 0.2294 | 0.096 (14)* | |
C1D | 0.7614 (2) | 0.1225 (2) | 0.15013 (18) | 0.0379 (7) | |
C11D | 0.8689 (2) | 0.1406 (2) | 0.1411 (2) | 0.0452 (8) | |
O10D | 0.93668 (15) | 0.14634 (17) | 0.20320 (13) | 0.0505 (6) | |
O11D | 0.88545 (18) | 0.1481 (2) | 0.07450 (16) | 0.0799 (9) | |
C2D | 0.7362 (2) | 0.1138 (2) | 0.22353 (19) | 0.0451 (8) | |
H2D | 0.7866 | 0.1201 | 0.2692 | 0.068 (11)* | |
C3D | 0.6363 (2) | 0.0956 (2) | 0.2289 (2) | 0.0488 (8) | |
H3D | 0.6185 | 0.0881 | 0.2774 | 0.052 (9)* | |
C4D | 0.5641 (2) | 0.0888 (2) | 0.16152 (19) | 0.0417 (7) | |
N41D | 0.4573 (2) | 0.0705 (2) | 0.16676 (19) | 0.0533 (7) | |
O41D | 0.43598 (19) | 0.0597 (2) | 0.23047 (18) | 0.0778 (8) | |
O42D | 0.39448 (19) | 0.0665 (2) | 0.10617 (17) | 0.0790 (8) | |
C5D | 0.5864 (2) | 0.0984 (2) | 0.08864 (19) | 0.0439 (8) | |
H5D | 0.5359 | 0.0942 | 0.0440 | 0.048 (9)* | |
C6D | 0.6857 (2) | 0.1146 (2) | 0.08335 (19) | 0.0436 (8) | |
H6D | 0.7022 | 0.1202 | 0.0340 | 0.043 (8)* | |
N1E | 0.17840 (19) | 0.2216 (2) | 0.30087 (16) | 0.0476 (7) | |
C2E | 0.2396 (3) | 0.2134 (3) | 0.2406 (2) | 0.0631 (10) | |
H21E | 0.3046 | 0.2103 | 0.2673 | 0.079* | |
H22E | 0.2530 | 0.2725 | 0.2227 | 0.079* | |
C3E | 0.1891 (3) | 0.1237 (3) | 0.1657 (2) | 0.0643 (10) | |
H31E | 0.2344 | 0.1209 | 0.1290 | 0.080* | |
H32E | 0.1769 | 0.0643 | 0.1832 | 0.080* | |
N4E | 0.0918 (2) | 0.1258 (2) | 0.11995 (17) | 0.0584 (8) | |
H41E | 0.1032 | 0.1785 | 0.1015 | 0.073* | |
H42E | 0.0503 | 0.1292 | 0.1536 | 0.073* | |
H43E | 0.0631 | 0.0709 | 0.0771 | 0.073* | |
C5E | 0.1896 (3) | 0.1558 (3) | 0.3521 (2) | 0.0618 (10) | |
H51E | 0.2535 | 0.1875 | 0.3943 | 0.077* | |
H52E | 0.1930 | 0.0948 | 0.3172 | 0.077* | |
C6E | 0.1043 (3) | 0.1311 (3) | 0.3936 (2) | 0.0663 (11) | |
H61E | 0.1200 | 0.0935 | 0.4306 | 0.083* | |
H62E | 0.0993 | 0.1921 | 0.4270 | 0.083* | |
N7E | 0.0047 (2) | 0.0729 (2) | 0.33348 (17) | 0.0561 (8) | |
H71E | 0.0089 | 0.0170 | 0.3023 | 0.070* | |
H72E | −0.0117 | 0.1084 | 0.3011 | 0.070* | |
H73E | −0.0430 | 0.0585 | 0.3609 | 0.070* | |
C8E | 0.2095 (3) | 0.3241 (3) | 0.3546 (2) | 0.0645 (10) | |
H81E | 0.2832 | 0.3522 | 0.3688 | 0.081* | |
H82E | 0.1884 | 0.3241 | 0.4057 | 0.081* | |
C9E | 0.1644 (3) | 0.3884 (3) | 0.3143 (3) | 0.0691 (11) | |
H91E | 0.1874 | 0.4553 | 0.3519 | 0.086* | |
H92E | 0.1875 | 0.3911 | 0.2644 | 0.086* | |
N10E | 0.0520 (2) | 0.3486 (2) | 0.29273 (18) | 0.0607 (8) | |
H11E | 0.0313 | 0.2843 | 0.2651 | 0.076* | |
H12E | 0.0266 | 0.3808 | 0.2612 | 0.076* | |
H13E | 0.0303 | 0.3568 | 0.3390 | 0.076* | |
C1F | 0.8313 (2) | 0.8858 (2) | 0.13756 (19) | 0.0440 (8) | |
C11F | 0.9408 (3) | 0.9074 (3) | 0.1325 (2) | 0.0541 (9) | |
O10F | 1.00613 (18) | 0.9165 (2) | 0.19669 (16) | 0.0679 (7) | |
O11F | 0.96044 (19) | 0.9148 (2) | 0.06593 (16) | 0.0691 (7) | |
C2F | 0.8020 (2) | 0.8684 (2) | 0.20736 (19) | 0.0463 (8) | |
H2F | 0.8504 | 0.8675 | 0.2512 | 0.056 (9)* | |
C3F | 0.7030 (2) | 0.8523 (2) | 0.2132 (2) | 0.0489 (8) | |
H3F | 0.6840 | 0.8415 | 0.2605 | 0.066 (11)* | |
C4F | 0.6324 (2) | 0.8528 (2) | 0.1467 (2) | 0.0461 (8) | |
N41F | 0.5266 (2) | 0.8391 (2) | 0.1532 (2) | 0.0605 (8) | |
O41F | 0.5054 (2) | 0.8243 (3) | 0.2159 (2) | 0.0991 (11) | |
O42F | 0.4652 (2) | 0.8442 (2) | 0.09592 (19) | 0.0808 (8) | |
C5F | 0.6576 (3) | 0.8677 (2) | 0.0759 (2) | 0.0504 (8) | |
H5F | 0.6086 | 0.8668 | 0.0316 | 0.078 (12)* | |
C6F | 0.7573 (3) | 0.8841 (2) | 0.07209 (19) | 0.0501 (8) | |
H6F | 0.7756 | 0.8942 | 0.0244 | 0.055 (9)* | |
C1G | 0.7114 (3) | 0.0466 (3) | 0.43131 (19) | 0.0518 (9) | |
C11G | 0.8025 (3) | 0.0115 (3) | 0.4328 (2) | 0.0513 (9) | |
O10G | 0.78887 (19) | −0.0785 (2) | 0.42110 (17) | 0.0704 (7) | |
O11G | 0.88729 (19) | 0.0770 (2) | 0.44582 (16) | 0.0700 (7) | |
C2G | 0.6145 (3) | −0.0226 (4) | 0.4117 (2) | 0.0634 (11) | |
H2G | 0.6060 | −0.0899 | 0.4007 | 0.069 (13)* | |
C3G | 0.5313 (3) | 0.0096 (5) | 0.4087 (3) | 0.0806 (14) | |
H3G | 0.4662 | −0.0362 | 0.3953 | 0.070 (12)* | |
C4G | 0.5435 (4) | 0.1066 (5) | 0.4252 (3) | 0.0832 (15) | |
N41G | 0.4513 (4) | 0.1376 (5) | 0.4196 (3) | 0.1053 (14) | |
O41G | 0.3696 (3) | 0.0709 (5) | 0.4071 (3) | 0.1473 (18) | |
O42G | 0.4649 (4) | 0.2245 (4) | 0.4240 (3) | 0.1398 (17) | |
C5G | 0.6370 (4) | 0.1767 (4) | 0.4451 (2) | 0.0870 (15) | |
H5G | 0.6441 | 0.2437 | 0.4568 | 0.103 (17)* | |
C6G | 0.7223 (3) | 0.1451 (4) | 0.4477 (2) | 0.0676 (11) | |
H6G | 0.7869 | 0.1916 | 0.4607 | 0.088 (14)* | |
C1H | 0.2770 (4) | 0.4423 (5) | 0.5777 (2) | 0.0870 (14) | |
C11H | 0.1838 (5) | 0.4770 (6) | 0.5689 (3) | 0.107 (2) | |
O10H | 0.1946 (4) | 0.5592 (4) | 0.5622 (3) | 0.1503 (19) | |
O11H | 0.1031 (3) | 0.4151 (4) | 0.5710 (3) | 0.1547 (19) | |
C2H | 0.3714 (4) | 0.5049 (4) | 0.5819 (3) | 0.0869 (14) | |
H2H | 0.3784 | 0.5684 | 0.5781 | 0.12 (2)* | |
C3H | 0.4552 (4) | 0.4751 (4) | 0.5917 (3) | 0.0850 (13) | |
H3H | 0.5189 | 0.5185 | 0.5953 | 0.102 (16)* | |
C4H | 0.4451 (3) | 0.3804 (4) | 0.5961 (2) | 0.0699 (11) | |
N41H | 0.5366 (3) | 0.3502 (4) | 0.6096 (2) | 0.0880 (11) | |
O41H | 0.6175 (3) | 0.4085 (3) | 0.6124 (3) | 0.1362 (16) | |
O42H | 0.5281 (3) | 0.2693 (3) | 0.6175 (2) | 0.1114 (12) | |
C5H | 0.3528 (3) | 0.3153 (4) | 0.5904 (2) | 0.0758 (12) | |
H5H | 0.3464 | 0.2513 | 0.5924 | 0.089 (16)* | |
C6H | 0.2685 (3) | 0.3466 (4) | 0.5813 (2) | 0.0826 (14) | |
H6H | 0.2049 | 0.3030 | 0.5776 | 0.125 (19)* | |
O1W | 0.0372 (2) | 0.1210 (3) | 0.59222 (16) | 0.0850 (9) | |
H11 | 0.085 (2) | 0.104 (3) | 0.583 (2) | 0.106* | |
H12 | −0.006 (2) | 0.098 (3) | 0.5489 (14) | 0.106* | |
O2W | 0.1096 (3) | 0.3148 (3) | 0.1019 (2) | 0.0901 (9) | |
H21 | 0.145 (3) | 0.343 (3) | 0.077 (3) | 0.113* | |
H22 | 0.063 (2) | 0.337 (3) | 0.103 (3) | 0.113* | |
O3W | 0.0445 (3) | 0.6493 (4) | 0.5815 (3) | 0.1350 (15) | |
H31 | 0.087 (3) | 0.625 (4) | 0.575 (4) | 0.169* | |
H32 | 0.010 (3) | 0.640 (3) | 0.535 (3) | 0.169* | |
O41W | 0.0850 (5) | 0.5832 (5) | 0.3957 (4) | 0.1074 (19) | 0.60 |
O42W | 0.0201 (8) | 0.5747 (7) | 0.3295 (6) | 0.116 (3) | 0.40 |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0318 (13) | 0.0497 (16) | 0.0411 (14) | 0.0154 (12) | 0.0104 (11) | 0.0133 (12) |
C2A | 0.0325 (17) | 0.063 (2) | 0.0515 (19) | 0.0190 (16) | 0.0101 (14) | 0.0169 (16) |
C3A | 0.044 (2) | 0.057 (2) | 0.068 (2) | 0.0229 (17) | 0.0137 (17) | 0.0241 (18) |
N4A | 0.0391 (15) | 0.0466 (16) | 0.0672 (18) | 0.0123 (13) | 0.0151 (13) | 0.0158 (14) |
C5A | 0.0429 (19) | 0.077 (2) | 0.0431 (19) | 0.0226 (18) | 0.0070 (15) | 0.0171 (17) |
C6A | 0.061 (2) | 0.085 (3) | 0.0434 (19) | 0.030 (2) | 0.0160 (17) | 0.0167 (19) |
N7A | 0.048 (2) | 0.137 (3) | 0.081 (3) | 0.028 (2) | 0.0139 (18) | −0.024 (2) |
C8A | 0.0418 (18) | 0.048 (2) | 0.0503 (19) | 0.0078 (15) | 0.0100 (15) | 0.0109 (16) |
C9A | 0.0416 (19) | 0.056 (2) | 0.061 (2) | 0.0151 (16) | 0.0197 (16) | 0.0231 (17) |
N10A | 0.0484 (16) | 0.075 (2) | 0.0507 (16) | 0.0311 (15) | 0.0180 (13) | 0.0283 (15) |
C1B | 0.0493 (19) | 0.0365 (17) | 0.0481 (19) | 0.0141 (15) | 0.0155 (15) | 0.0154 (14) |
C11B | 0.049 (2) | 0.051 (2) | 0.063 (2) | 0.0180 (17) | 0.0161 (18) | 0.0248 (18) |
O10B | 0.0490 (16) | 0.119 (2) | 0.091 (2) | 0.0231 (15) | 0.0161 (15) | 0.0632 (18) |
O11B | 0.0714 (18) | 0.0801 (18) | 0.0611 (16) | 0.0258 (14) | 0.0327 (13) | 0.0295 (14) |
C2B | 0.048 (2) | 0.053 (2) | 0.0478 (19) | 0.0132 (16) | 0.0078 (16) | 0.0171 (16) |
C3B | 0.063 (2) | 0.052 (2) | 0.055 (2) | 0.0131 (18) | 0.0239 (19) | 0.0180 (17) |
C4B | 0.045 (2) | 0.046 (2) | 0.075 (3) | 0.0102 (16) | 0.0208 (19) | 0.0116 (18) |
N41B | 0.055 (2) | 0.086 (3) | 0.095 (3) | 0.0112 (19) | 0.028 (2) | 0.014 (2) |
O41B | 0.079 (2) | 0.158 (4) | 0.113 (3) | 0.010 (2) | 0.055 (2) | 0.038 (3) |
O42B | 0.055 (2) | 0.167 (4) | 0.139 (3) | 0.033 (2) | 0.027 (2) | 0.035 (3) |
C5B | 0.047 (2) | 0.055 (2) | 0.058 (2) | 0.0205 (17) | 0.0044 (18) | 0.0127 (17) |
C6B | 0.056 (2) | 0.049 (2) | 0.047 (2) | 0.0193 (17) | 0.0091 (16) | 0.0152 (16) |
C1C | 0.0410 (18) | 0.0385 (18) | 0.058 (2) | 0.0145 (14) | 0.0111 (16) | 0.0134 (15) |
C11C | 0.054 (2) | 0.053 (2) | 0.094 (3) | 0.0223 (19) | 0.031 (2) | 0.019 (2) |
O10C | 0.106 (3) | 0.172 (3) | 0.152 (3) | 0.086 (2) | 0.092 (2) | 0.111 (3) |
O11C | 0.0410 (16) | 0.136 (3) | 0.099 (2) | 0.0335 (17) | −0.0011 (16) | −0.033 (2) |
C2C | 0.058 (2) | 0.059 (2) | 0.053 (2) | 0.0269 (18) | 0.0214 (17) | 0.0253 (17) |
C3C | 0.049 (2) | 0.065 (2) | 0.048 (2) | 0.0281 (18) | 0.0019 (16) | 0.0133 (17) |
C4C | 0.0355 (17) | 0.0467 (19) | 0.052 (2) | 0.0130 (14) | 0.0111 (15) | 0.0060 (15) |
N41C | 0.0478 (19) | 0.084 (2) | 0.065 (2) | 0.0256 (17) | 0.0144 (17) | 0.0047 (18) |
O41C | 0.0586 (18) | 0.152 (3) | 0.093 (2) | 0.059 (2) | 0.0130 (17) | 0.015 (2) |
O42C | 0.072 (2) | 0.166 (4) | 0.112 (3) | 0.033 (2) | 0.050 (2) | 0.054 (3) |
C5C | 0.052 (2) | 0.053 (2) | 0.0404 (18) | 0.0170 (16) | 0.0136 (15) | 0.0128 (15) |
C6C | 0.0417 (19) | 0.051 (2) | 0.0440 (18) | 0.0152 (15) | 0.0014 (15) | 0.0092 (15) |
C1D | 0.0335 (16) | 0.0383 (17) | 0.0409 (17) | 0.0099 (13) | 0.0059 (13) | 0.0144 (14) |
C11D | 0.0327 (17) | 0.056 (2) | 0.051 (2) | 0.0135 (15) | 0.0081 (15) | 0.0263 (16) |
O10D | 0.0324 (11) | 0.0679 (15) | 0.0517 (13) | 0.0139 (10) | 0.0055 (10) | 0.0253 (11) |
O11D | 0.0468 (15) | 0.153 (3) | 0.0652 (17) | 0.0376 (16) | 0.0245 (13) | 0.0654 (18) |
C2D | 0.0371 (18) | 0.058 (2) | 0.0398 (17) | 0.0147 (15) | 0.0024 (14) | 0.0199 (15) |
C3D | 0.0438 (19) | 0.065 (2) | 0.0423 (18) | 0.0161 (16) | 0.0127 (15) | 0.0255 (16) |
C4D | 0.0299 (16) | 0.0436 (18) | 0.0519 (19) | 0.0108 (14) | 0.0079 (14) | 0.0180 (15) |
N41D | 0.0366 (16) | 0.0616 (19) | 0.0615 (19) | 0.0136 (13) | 0.0137 (15) | 0.0201 (15) |
O41D | 0.0515 (16) | 0.115 (2) | 0.0796 (19) | 0.0244 (15) | 0.0319 (14) | 0.0452 (17) |
O42D | 0.0397 (14) | 0.129 (3) | 0.0730 (18) | 0.0332 (15) | 0.0074 (13) | 0.0367 (17) |
C5D | 0.0319 (16) | 0.054 (2) | 0.0415 (18) | 0.0133 (14) | −0.0009 (14) | 0.0155 (15) |
C6D | 0.0409 (18) | 0.054 (2) | 0.0393 (17) | 0.0157 (15) | 0.0080 (14) | 0.0203 (15) |
N1E | 0.0321 (14) | 0.0645 (19) | 0.0464 (15) | 0.0149 (13) | 0.0070 (12) | 0.0201 (14) |
C2E | 0.0322 (18) | 0.094 (3) | 0.067 (2) | 0.0200 (19) | 0.0156 (17) | 0.030 (2) |
C3E | 0.047 (2) | 0.094 (3) | 0.068 (2) | 0.041 (2) | 0.0246 (18) | 0.025 (2) |
N4E | 0.0483 (17) | 0.077 (2) | 0.0531 (17) | 0.0255 (15) | 0.0156 (14) | 0.0169 (15) |
C5E | 0.0407 (19) | 0.088 (3) | 0.060 (2) | 0.0234 (19) | 0.0032 (16) | 0.032 (2) |
C6E | 0.052 (2) | 0.091 (3) | 0.054 (2) | 0.014 (2) | 0.0029 (17) | 0.036 (2) |
N7E | 0.0446 (16) | 0.076 (2) | 0.0536 (17) | 0.0160 (15) | 0.0128 (13) | 0.0335 (15) |
C8E | 0.041 (2) | 0.076 (3) | 0.058 (2) | 0.0056 (18) | −0.0034 (17) | 0.014 (2) |
C9E | 0.057 (2) | 0.064 (2) | 0.075 (3) | 0.012 (2) | 0.008 (2) | 0.015 (2) |
N10E | 0.066 (2) | 0.0610 (19) | 0.0576 (18) | 0.0280 (16) | 0.0093 (15) | 0.0179 (15) |
C1F | 0.0475 (19) | 0.0413 (18) | 0.0436 (18) | 0.0160 (15) | 0.0120 (15) | 0.0110 (14) |
C11F | 0.050 (2) | 0.052 (2) | 0.062 (2) | 0.0209 (17) | 0.0189 (19) | 0.0114 (18) |
O10F | 0.0457 (14) | 0.092 (2) | 0.0734 (17) | 0.0316 (14) | 0.0151 (13) | 0.0266 (15) |
O11F | 0.0637 (17) | 0.0859 (19) | 0.0568 (16) | 0.0197 (14) | 0.0322 (13) | 0.0136 (14) |
C2F | 0.0449 (19) | 0.051 (2) | 0.0433 (18) | 0.0163 (16) | 0.0069 (15) | 0.0175 (15) |
C3F | 0.051 (2) | 0.052 (2) | 0.0419 (18) | 0.0101 (16) | 0.0152 (15) | 0.0161 (15) |
C4F | 0.0363 (17) | 0.0438 (19) | 0.051 (2) | 0.0088 (14) | 0.0063 (15) | 0.0100 (15) |
N41F | 0.0419 (17) | 0.060 (2) | 0.066 (2) | 0.0055 (14) | 0.0137 (16) | 0.0075 (16) |
O41F | 0.0507 (17) | 0.157 (3) | 0.079 (2) | 0.0117 (18) | 0.0271 (15) | 0.035 (2) |
O42F | 0.0448 (15) | 0.095 (2) | 0.091 (2) | 0.0191 (15) | 0.0000 (15) | 0.0230 (17) |
C5F | 0.051 (2) | 0.050 (2) | 0.0439 (19) | 0.0142 (16) | 0.0016 (16) | 0.0137 (16) |
C6F | 0.056 (2) | 0.056 (2) | 0.0401 (18) | 0.0186 (17) | 0.0133 (16) | 0.0169 (16) |
C1G | 0.044 (2) | 0.088 (3) | 0.0338 (17) | 0.0335 (19) | 0.0120 (14) | 0.0226 (17) |
C11G | 0.040 (2) | 0.083 (3) | 0.0407 (18) | 0.030 (2) | 0.0104 (15) | 0.0231 (18) |
O10G | 0.0523 (16) | 0.088 (2) | 0.0829 (19) | 0.0370 (15) | 0.0184 (13) | 0.0308 (16) |
O11G | 0.0402 (15) | 0.096 (2) | 0.0752 (17) | 0.0254 (14) | 0.0157 (12) | 0.0237 (15) |
C2G | 0.045 (2) | 0.098 (3) | 0.061 (2) | 0.034 (2) | 0.0177 (17) | 0.034 (2) |
C3G | 0.043 (2) | 0.156 (5) | 0.067 (3) | 0.047 (3) | 0.0214 (19) | 0.053 (3) |
C4G | 0.077 (3) | 0.162 (5) | 0.055 (2) | 0.090 (4) | 0.028 (2) | 0.046 (3) |
N41G | 0.097 (3) | 0.151 (4) | 0.087 (3) | 0.071 (3) | 0.011 (2) | 0.042 (3) |
O41G | 0.094 (3) | 0.259 (5) | 0.162 (4) | 0.108 (3) | 0.058 (3) | 0.117 (4) |
O42G | 0.137 (3) | 0.193 (4) | 0.109 (3) | 0.122 (3) | 0.010 (2) | 0.017 (3) |
C5G | 0.095 (4) | 0.122 (4) | 0.055 (2) | 0.074 (3) | 0.003 (2) | 0.012 (2) |
C6G | 0.061 (3) | 0.093 (3) | 0.047 (2) | 0.036 (2) | 0.0019 (18) | 0.014 (2) |
C1H | 0.072 (3) | 0.126 (4) | 0.047 (2) | 0.037 (3) | 0.005 (2) | −0.003 (3) |
C11H | 0.071 (4) | 0.167 (6) | 0.069 (3) | 0.053 (4) | −0.001 (3) | 0.004 (4) |
O10H | 0.117 (4) | 0.170 (5) | 0.160 (4) | 0.080 (4) | 0.004 (3) | 0.024 (4) |
O11H | 0.067 (3) | 0.228 (5) | 0.156 (4) | 0.053 (3) | 0.010 (3) | 0.041 (4) |
C2H | 0.074 (3) | 0.104 (4) | 0.076 (3) | 0.034 (3) | 0.014 (2) | 0.012 (3) |
C3H | 0.063 (3) | 0.093 (4) | 0.087 (3) | 0.018 (3) | 0.022 (2) | 0.011 (3) |
C4H | 0.054 (2) | 0.091 (3) | 0.057 (2) | 0.020 (2) | 0.0154 (19) | 0.011 (2) |
N41H | 0.069 (3) | 0.107 (3) | 0.082 (3) | 0.028 (3) | 0.019 (2) | 0.018 (2) |
O41H | 0.066 (2) | 0.145 (4) | 0.206 (5) | 0.036 (2) | 0.049 (3) | 0.056 (3) |
O42H | 0.102 (3) | 0.119 (3) | 0.117 (3) | 0.048 (2) | 0.013 (2) | 0.040 (2) |
C5H | 0.068 (3) | 0.092 (4) | 0.053 (2) | 0.017 (2) | 0.015 (2) | 0.009 (2) |
C6H | 0.051 (3) | 0.123 (4) | 0.043 (2) | 0.009 (3) | 0.0051 (18) | −0.002 (2) |
O1W | 0.0657 (19) | 0.142 (3) | 0.0572 (16) | 0.063 (2) | 0.0152 (14) | 0.0142 (17) |
O2W | 0.085 (2) | 0.105 (3) | 0.095 (2) | 0.041 (2) | 0.0274 (18) | 0.0422 (19) |
O3W | 0.094 (3) | 0.213 (5) | 0.096 (3) | 0.063 (3) | 0.025 (2) | 0.028 (3) |
O41W | 0.130 (5) | 0.114 (5) | 0.107 (5) | 0.057 (4) | 0.052 (4) | 0.049 (4) |
O42W | 0.130 (8) | 0.098 (7) | 0.107 (7) | 0.018 (6) | 0.029 (6) | 0.028 (6) |
Geometric parameters (Å, º) top
N1A—C8A | 1.465 (4) | C2E—H21E | 0.97 |
N1A—C5A | 1.469 (4) | C2E—H22E | 0.97 |
N1A—C2A | 1.473 (4) | C3E—N4E | 1.472 (4) |
C2A—C3A | 1.516 (5) | C3E—H31E | 0.97 |
C2A—H21A | 0.97 | C3E—H32E | 0.97 |
C2A—H22A | 0.97 | N4E—H41E | 0.89 |
C3A—N4A | 1.483 (4) | N4E—H42E | 0.89 |
C3A—H31A | 0.97 | N4E—H43E | 0.89 |
C3A—H32A | 0.97 | C5E—C6E | 1.503 (5) |
N4A—H41A | 0.89 | C5E—H51E | 0.97 |
N4A—H42A | 0.89 | C5E—H52E | 0.97 |
N4A—H43A | 0.89 | C6E—N7E | 1.483 (4) |
C5A—C6A | 1.508 (5) | C6E—H61E | 0.97 |
C5A—H51A | 0.97 | C6E—H62E | 0.97 |
C5A—H52A | 0.97 | N7E—H71E | 0.89 |
C6A—N7A | 1.474 (5) | N7E—H72E | 0.89 |
C6A—H61A | 0.97 | N7E—H73E | 0.89 |
C6A—H62A | 0.97 | C8E—C9E | 1.504 (5) |
N7A—H71A | 0.89 | C8E—H81E | 0.97 |
N7A—H72A | 0.89 | C8E—H82E | 0.97 |
N7A—H73A | 0.89 | C9E—N10E | 1.477 (5) |
C8A—C9A | 1.510 (5) | C9E—H91E | 0.97 |
C8A—H81A | 0.97 | C9E—H92E | 0.97 |
C8A—H82A | 0.97 | N10E—H11E | 0.89 |
C9A—N10A | 1.486 (4) | N10E—H12E | 0.89 |
C9A—H91A | 0.97 | N10E—H13E | 0.89 |
C9A—H92A | 0.97 | C1F—C2F | 1.386 (4) |
N10A—H11A | 0.89 | C1F—C6F | 1.387 (4) |
N10A—H12A | 0.89 | C1F—C11F | 1.510 (5) |
N10A—H13A | 0.89 | C11F—O11F | 1.241 (4) |
C1B—C6B | 1.384 (4) | C11F—O10F | 1.263 (4) |
C1B—C2B | 1.393 (4) | C2F—C3F | 1.376 (5) |
C1B—C11B | 1.511 (5) | C2F—H2F | 0.93 |
C11B—O11B | 1.236 (4) | C3F—C4F | 1.383 (4) |
C11B—O10B | 1.253 (4) | C3F—H3F | 0.93 |
C2B—C3B | 1.384 (5) | C4F—C5F | 1.370 (5) |
C2B—H2B | 0.93 | C4F—N41F | 1.475 (4) |
C3B—C4B | 1.376 (5) | N41F—O41F | 1.214 (4) |
C3B—H3B | 0.93 | N41F—O42F | 1.226 (4) |
C4B—C5B | 1.376 (5) | C5F—C6F | 1.375 (5) |
C4B—N41B | 1.464 (5) | C5F—H5F | 0.93 |
N41B—O41B | 1.217 (5) | C6F—H6F | 0.93 |
N41B—O42B | 1.224 (5) | C1G—C6G | 1.367 (5) |
C5B—C6B | 1.370 (5) | C1G—C2G | 1.391 (5) |
C5B—H5B | 0.93 | C1G—C11G | 1.509 (5) |
C6B—H6B | 0.93 | C11G—O10G | 1.245 (4) |
C1C—C6C | 1.380 (5) | C11G—O11G | 1.258 (4) |
C1C—C2C | 1.381 (4) | C2G—C3G | 1.378 (5) |
C1C—C11C | 1.517 (5) | C2G—H2G | 0.93 |
C11C—O10C | 1.240 (5) | C3G—C4G | 1.342 (7) |
C11C—O11C | 1.249 (5) | C3G—H3G | 0.93 |
C2C—C3C | 1.369 (5) | C4G—C5G | 1.361 (7) |
C2C—H2C | 0.93 | C4G—N41G | 1.486 (6) |
C3C—C4C | 1.369 (5) | N41G—O42G | 1.220 (6) |
C3C—H3C | 0.93 | N41G—O41G | 1.237 (6) |
C4C—C5C | 1.379 (4) | C5G—C6G | 1.399 (6) |
C4C—N41C | 1.478 (4) | C5G—H5G | 0.93 |
N41C—O42C | 1.197 (4) | C6G—H6G | 0.93 |
N41C—O41C | 1.212 (4) | C1H—C2H | 1.374 (7) |
C5C—C6C | 1.384 (5) | C1H—C6H | 1.395 (7) |
C5C—H5C | 0.93 | C1H—C11H | 1.532 (7) |
C6C—H6C | 0.93 | C11H—O10H | 1.211 (8) |
C1D—C6D | 1.385 (4) | C11H—O11H | 1.259 (8) |
C1D—C2D | 1.388 (4) | C2H—C3H | 1.366 (6) |
C1D—C11D | 1.506 (4) | C2H—H2H | 0.93 |
C11D—O11D | 1.227 (4) | C3H—C4H | 1.382 (6) |
C11D—O10D | 1.273 (3) | C3H—H3H | 0.93 |
C2D—C3D | 1.383 (4) | C4H—C5H | 1.359 (6) |
C2D—H2D | 0.93 | C4H—N41H | 1.475 (6) |
C3D—C4D | 1.368 (4) | N41H—O42H | 1.204 (5) |
C3D—H3D | 0.93 | N41H—O41H | 1.209 (5) |
C4D—C5D | 1.367 (4) | C5H—C6H | 1.385 (6) |
C4D—N41D | 1.477 (4) | C5H—H5H | 0.93 |
N41D—O41D | 1.214 (4) | C6H—H6H | 0.93 |
N41D—O42D | 1.223 (4) | O1W—H11 | 0.81 (3) |
C5D—C6D | 1.377 (4) | O1W—H12 | 0.81 (3) |
C5D—H5D | 0.93 | O2W—H21 | 0.80 (5) |
C6D—H6D | 0.93 | O2W—H22 | 0.81 (3) |
N1E—C2E | 1.457 (4) | O3W—H31 | 0.82 (5) |
N1E—C8E | 1.467 (5) | O3W—H32 | 0.82 (5) |
N1E—C5E | 1.472 (4) | O41W—O42W | 1.287 (11) |
C2E—C3E | 1.505 (5) | ||
C8A—N1A—C5A | 109.6 (2) | C8E—N1E—C5E | 109.5 (3) |
C8A—N1A—C2A | 111.3 (2) | N1E—C2E—C3E | 113.1 (3) |
C5A—N1A—C2A | 109.8 (2) | N1E—C2E—H21E | 109.0 |
N1A—C2A—C3A | 112.2 (3) | C3E—C2E—H21E | 109.0 |
N1A—C2A—H21A | 109.2 | N1E—C2E—H22E | 109.0 |
C3A—C2A—H21A | 109.2 | C3E—C2E—H22E | 109.0 |
N1A—C2A—H22A | 109.1 | H21E—C2E—H22E | 107.8 |
C3A—C2A—H22A | 109.2 | N4E—C3E—C2E | 111.9 (3) |
H21A—C2A—H22A | 107.9 | N4E—C3E—H31E | 109.2 |
N4A—C3A—C2A | 110.2 (3) | C2E—C3E—H31E | 109.2 |
N4A—C3A—H31A | 109.6 | N4E—C3E—H32E | 109.3 |
C2A—C3A—H31A | 109.6 | C2E—C3E—H32E | 109.2 |
N4A—C3A—H32A | 109.6 | H31E—C3E—H32E | 107.9 |
C2A—C3A—H32A | 109.6 | C3E—N4E—H41E | 109.5 |
H31A—C3A—H32A | 108.1 | C3E—N4E—H42E | 109.5 |
C3A—N4A—H41A | 109.5 | H41E—N4E—H42E | 109.5 |
C3A—N4A—H42A | 109.5 | C3E—N4E—H43E | 109.5 |
H41A—N4A—H42A | 109.5 | H41E—N4E—H43E | 109.5 |
C3A—N4A—H43A | 109.5 | H42E—N4E—H43E | 109.5 |
H41A—N4A—H43A | 109.5 | N1E—C5E—C6E | 113.4 (3) |
H42A—N4A—H43A | 109.5 | N1E—C5E—H51E | 108.9 |
N1A—C5A—C6A | 113.4 (3) | C6E—C5E—H51E | 108.9 |
N1A—C5A—H51A | 108.9 | N1E—C5E—H52E | 108.9 |
C6A—C5A—H51A | 108.9 | C6E—C5E—H52E | 108.9 |
N1A—C5A—H52A | 108.9 | H51E—C5E—H52E | 107.7 |
C6A—C5A—H52A | 108.9 | N7E—C6E—C5E | 112.7 (3) |
H51A—C5A—H52A | 107.7 | N7E—C6E—H61E | 109.0 |
N7A—C6A—C5A | 111.9 (3) | C5E—C6E—H61E | 109.0 |
N7A—C6A—H61A | 109.2 | N7E—C6E—H62E | 109.0 |
C5A—C6A—H61A | 109.2 | C5E—C6E—H62E | 109.0 |
N7A—C6A—H62A | 109.3 | H61E—C6E—H62E | 107.8 |
C5A—C6A—H62A | 109.2 | C6E—N7E—H71E | 109.5 |
H61A—C6A—H62A | 107.9 | C6E—N7E—H72E | 109.5 |
C6A—N7A—H71A | 109.5 | H71E—N7E—H72E | 109.5 |
C6A—N7A—H72A | 109.5 | C6E—N7E—H73E | 109.5 |
H71A—N7A—H72A | 109.5 | H71E—N7E—H73E | 109.5 |
C6A—N7A—H73A | 109.5 | H72E—N7E—H73E | 109.5 |
H71A—N7A—H73A | 109.5 | N1E—C8E—C9E | 112.6 (3) |
H72A—N7A—H73A | 109.5 | N1E—C8E—H81E | 109.1 |
N1A—C8A—C9A | 113.5 (3) | C9E—C8E—H81E | 109.1 |
N1A—C8A—H81A | 108.9 | N1E—C8E—H82E | 109.1 |
C9A—C8A—H81A | 108.9 | C9E—C8E—H82E | 109.1 |
N1A—C8A—H82A | 108.9 | H81E—C8E—H82E | 107.8 |
C9A—C8A—H82A | 108.9 | N10E—C9E—C8E | 110.6 (3) |
H81A—C8A—H82A | 107.7 | N10E—C9E—H91E | 109.5 |
N10A—C9A—C8A | 112.5 (3) | C8E—C9E—H91E | 109.5 |
N10A—C9A—H91A | 109.1 | N10E—C9E—H92E | 109.5 |
C8A—C9A—H91A | 109.1 | C8E—C9E—H92E | 109.5 |
N10A—C9A—H92A | 109.1 | H91E—C9E—H92E | 108.1 |
C8A—C9A—H92A | 109.1 | C9E—N10E—H11E | 109.5 |
H91A—C9A—H92A | 107.8 | C9E—N10E—H12E | 109.5 |
C9A—N10A—H11A | 109.5 | H11E—N10E—H12E | 109.5 |
C9A—N10A—H12A | 109.5 | C9E—N10E—H13E | 109.5 |
H11A—N10A—H12A | 109.5 | H11E—N10E—H13E | 109.5 |
C9A—N10A—H13A | 109.5 | H12E—N10E—H13E | 109.5 |
H11A—N10A—H13A | 109.5 | C2F—C1F—C6F | 118.2 (3) |
H12A—N10A—H13A | 109.5 | C2F—C1F—C11F | 121.4 (3) |
C6B—C1B—C2B | 118.9 (3) | C6F—C1F—C11F | 120.4 (3) |
C6B—C1B—C11B | 119.7 (3) | O11F—C11F—O10F | 124.5 (3) |
C2B—C1B—C11B | 121.4 (3) | O11F—C11F—C1F | 118.0 (3) |
O11B—C11B—O10B | 123.8 (3) | O10F—C11F—C1F | 117.5 (3) |
O11B—C11B—C1B | 118.3 (3) | C3F—C2F—C1F | 121.4 (3) |
O10B—C11B—C1B | 118.0 (3) | C3F—C2F—H2F | 119.3 |
C3B—C2B—C1B | 120.8 (3) | C1F—C2F—H2F | 119.3 |
C3B—C2B—H2B | 119.6 | C2F—C3F—C4F | 118.1 (3) |
C1B—C2B—H2B | 119.6 | C2F—C3F—H3F | 120.9 |
C4B—C3B—C2B | 117.9 (3) | C4F—C3F—H3F | 120.9 |
C4B—C3B—H3B | 121.0 | C5F—C4F—C3F | 122.4 (3) |
C2B—C3B—H3B | 121.0 | C5F—C4F—N41F | 118.8 (3) |
C5B—C4B—C3B | 122.7 (3) | C3F—C4F—N41F | 118.8 (3) |
C5B—C4B—N41B | 118.6 (4) | O41F—N41F—O42F | 123.4 (3) |
C3B—C4B—N41B | 118.7 (4) | O41F—N41F—C4F | 117.8 (3) |
O41B—N41B—O42B | 123.9 (4) | O42F—N41F—C4F | 118.8 (3) |
O41B—N41B—C4B | 117.9 (4) | C4F—C5F—C6F | 118.1 (3) |
O42B—N41B—C4B | 118.2 (4) | C4F—C5F—H5F | 121.0 |
C6B—C5B—C4B | 118.4 (3) | C6F—C5F—H5F | 120.9 |
C6B—C5B—H5B | 120.8 | C5F—C6F—C1F | 121.7 (3) |
C4B—C5B—H5B | 120.8 | C5F—C6F—H6F | 119.1 |
C5B—C6B—C1B | 121.3 (3) | C1F—C6F—H6F | 119.1 |
C5B—C6B—H6B | 119.4 | C6G—C1G—C2G | 119.5 (4) |
C1B—C6B—H6B | 119.4 | C6G—C1G—C11G | 121.1 (3) |
C6C—C1C—C2C | 119.7 (3) | C2G—C1G—C11G | 119.4 (4) |
C6C—C1C—C11C | 120.3 (3) | O10G—C11G—O11G | 125.1 (3) |
C2C—C1C—C11C | 120.0 (3) | O10G—C11G—C1G | 118.5 (3) |
O10C—C11C—O11C | 124.3 (4) | O11G—C11G—C1G | 116.4 (4) |
O10C—C11C—C1C | 117.9 (4) | C3G—C2G—C1G | 119.2 (4) |
O11C—C11C—C1C | 117.7 (4) | C3G—C2G—H2G | 120.4 |
C3C—C2C—C1C | 120.1 (3) | C1G—C2G—H2G | 120.4 |
C3C—C2C—H2C | 119.9 | C4G—C3G—C2G | 120.5 (4) |
C1C—C2C—H2C | 119.9 | C4G—C3G—H3G | 119.8 |
C4C—C3C—C2C | 119.4 (3) | C2G—C3G—H3G | 119.8 |
C4C—C3C—H3C | 120.3 | C3G—C4G—C5G | 122.2 (4) |
C2C—C3C—H3C | 120.3 | C3G—C4G—N41G | 118.5 (5) |
C3C—C4C—C5C | 122.0 (3) | C5G—C4G—N41G | 119.4 (6) |
C3C—C4C—N41C | 118.8 (3) | O42G—N41G—O41G | 128.1 (5) |
C5C—C4C—N41C | 119.1 (3) | O42G—N41G—C4G | 116.0 (6) |
O42C—N41C—O41C | 124.2 (4) | O41G—N41G—C4G | 115.8 (6) |
O42C—N41C—C4C | 118.1 (3) | C4G—C5G—C6G | 118.1 (5) |
O41C—N41C—C4C | 117.7 (4) | C4G—C5G—H5G | 121.0 |
C4C—C5C—C6C | 117.8 (3) | C6G—C5G—H5G | 121.0 |
C4C—C5C—H5C | 121.1 | C1G—C6G—C5G | 120.6 (5) |
C6C—C5C—H5C | 121.1 | C1G—C6G—H6G | 119.7 |
C1C—C6C—C5C | 120.8 (3) | C5G—C6G—H6G | 119.7 |
C1C—C6C—H6C | 119.6 | C2H—C1H—C6H | 118.3 (5) |
C5C—C6C—H6C | 119.6 | C2H—C1H—C11H | 120.6 (6) |
C6D—C1D—C2D | 119.1 (3) | C6H—C1H—C11H | 121.1 (6) |
C6D—C1D—C11D | 119.1 (3) | O10H—C11H—O11H | 127.1 (6) |
C2D—C1D—C11D | 121.8 (3) | O10H—C11H—C1H | 118.4 (7) |
O11D—C11D—O10D | 124.3 (3) | O11H—C11H—C1H | 114.5 (7) |
O11D—C11D—C1D | 118.1 (3) | C3H—C2H—C1H | 120.8 (6) |
O10D—C11D—C1D | 117.7 (3) | C3H—C2H—H2H | 119.6 |
C3D—C2D—C1D | 120.1 (3) | C1H—C2H—H2H | 119.6 |
C3D—C2D—H2D | 120.0 | C2H—C3H—C4H | 119.9 (5) |
C1D—C2D—H2D | 120.0 | C2H—C3H—H3H | 120.1 |
C4D—C3D—C2D | 118.8 (3) | C4H—C3H—H3H | 120.1 |
C4D—C3D—H3D | 120.6 | C5H—C4H—C3H | 121.3 (4) |
C2D—C3D—H3D | 120.6 | C5H—C4H—N41H | 119.4 (5) |
C5D—C4D—C3D | 122.7 (3) | C3H—C4H—N41H | 119.3 (4) |
C5D—C4D—N41D | 117.9 (3) | O42H—N41H—O41H | 122.8 (5) |
C3D—C4D—N41D | 119.3 (3) | O42H—N41H—C4H | 119.1 (4) |
O41D—N41D—O42D | 123.3 (3) | O41H—N41H—C4H | 118.1 (5) |
O41D—N41D—C4D | 118.6 (3) | C4H—C5H—C6H | 118.4 (5) |
O42D—N41D—C4D | 118.1 (3) | C4H—C5H—H5H | 120.8 |
C4D—C5D—C6D | 118.0 (3) | C6H—C5H—H5H | 120.8 |
C4D—C5D—H5D | 121.0 | C5H—C6H—C1H | 121.4 (5) |
C6D—C5D—H5D | 121.0 | C5H—C6H—H6H | 119.3 |
C5D—C6D—C1D | 121.2 (3) | C1H—C6H—H6H | 119.3 |
C5D—C6D—H6D | 119.4 | H11—O1W—H12 | 106 (3) |
C1D—C6D—H6D | 119.4 | H21—O2W—H22 | 107 (4) |
C2E—N1E—C8E | 110.7 (3) | H31—O3W—H32 | 106 (5) |
C2E—N1E—C5E | 109.9 (3) | ||
C8A—N1A—C2A—C3A | −154.6 (3) | C8E—N1E—C2E—C3E | −158.5 (3) |
C5A—N1A—C2A—C3A | 83.9 (3) | C5E—N1E—C2E—C3E | 80.4 (4) |
N1A—C2A—C3A—N4A | 59.7 (4) | N1E—C2E—C3E—N4E | 61.2 (4) |
C8A—N1A—C5A—C6A | 75.6 (4) | C2E—N1E—C5E—C6E | −159.4 (3) |
C2A—N1A—C5A—C6A | −161.8 (3) | C8E—N1E—C5E—C6E | 78.7 (4) |
N1A—C5A—C6A—N7A | 78.2 (4) | N1E—C5E—C6E—N7E | 64.6 (4) |
C5A—N1A—C8A—C9A | −165.3 (3) | C2E—N1E—C8E—C9E | 80.7 (4) |
C2A—N1A—C8A—C9A | 73.0 (3) | C5E—N1E—C8E—C9E | −158.0 (3) |
N1A—C8A—C9A—N10A | 58.2 (4) | N1E—C8E—C9E—N10E | 59.5 (4) |
C6B—C1B—C11B—O11B | −2.9 (5) | C2F—C1F—C11F—O11F | 174.6 (3) |
C2B—C1B—C11B—O11B | 176.7 (3) | C6F—C1F—C11F—O11F | −6.1 (5) |
C6B—C1B—C11B—O10B | 177.4 (3) | C2F—C1F—C11F—O10F | −5.3 (5) |
C2B—C1B—C11B—O10B | −2.9 (5) | C6F—C1F—C11F—O10F | 174.0 (3) |
C6B—C1B—C2B—C3B | 1.3 (5) | C6F—C1F—C2F—C3F | −1.7 (5) |
C11B—C1B—C2B—C3B | −178.4 (3) | C11F—C1F—C2F—C3F | 177.6 (3) |
C1B—C2B—C3B—C4B | −1.1 (5) | C1F—C2F—C3F—C4F | 0.8 (5) |
C2B—C3B—C4B—C5B | 0.4 (5) | C2F—C3F—C4F—C5F | 0.6 (5) |
C2B—C3B—C4B—N41B | 180.0 (3) | C2F—C3F—C4F—N41F | −177.9 (3) |
C5B—C4B—N41B—O41B | 172.0 (4) | C5F—C4F—N41F—O41F | 178.8 (3) |
C3B—C4B—N41B—O41B | −7.6 (6) | C3F—C4F—N41F—O41F | −2.7 (5) |
C5B—C4B—N41B—O42B | −6.5 (6) | C5F—C4F—N41F—O42F | −2.0 (5) |
C3B—C4B—N41B—O42B | 173.9 (4) | C3F—C4F—N41F—O42F | 176.5 (3) |
C3B—C4B—C5B—C6B | 0.1 (5) | C3F—C4F—C5F—C6F | −0.9 (5) |
N41B—C4B—C5B—C6B | −179.5 (3) | N41F—C4F—C5F—C6F | 177.6 (3) |
C4B—C5B—C6B—C1B | 0.1 (5) | C4F—C5F—C6F—C1F | −0.1 (5) |
C2B—C1B—C6B—C5B | −0.8 (5) | C2F—C1F—C6F—C5F | 1.4 (5) |
C11B—C1B—C6B—C5B | 178.8 (3) | C11F—C1F—C6F—C5F | −177.9 (3) |
C6C—C1C—C11C—O10C | 169.4 (4) | C6G—C1G—C11G—O10G | 176.8 (3) |
C2C—C1C—C11C—O10C | −9.5 (5) | C2G—C1G—C11G—O10G | −4.2 (5) |
C6C—C1C—C11C—O11C | −6.2 (5) | C6G—C1G—C11G—O11G | −3.3 (5) |
C2C—C1C—C11C—O11C | 174.9 (3) | C2G—C1G—C11G—O11G | 175.7 (3) |
C6C—C1C—C2C—C3C | 1.3 (5) | C6G—C1G—C2G—C3G | 0.4 (5) |
C11C—C1C—C2C—C3C | −179.8 (3) | C11G—C1G—C2G—C3G | −178.7 (3) |
C1C—C2C—C3C—C4C | −1.5 (5) | C1G—C2G—C3G—C4G | −0.5 (6) |
C2C—C3C—C4C—C5C | 0.3 (5) | C2G—C3G—C4G—C5G | 0.0 (6) |
C2C—C3C—C4C—N41C | −179.4 (3) | C2G—C3G—C4G—N41G | 178.8 (3) |
C3C—C4C—N41C—O42C | 169.3 (4) | C3G—C4G—N41G—O42G | −170.6 (4) |
C5C—C4C—N41C—O42C | −10.5 (5) | C5G—C4G—N41G—O42G | 8.3 (6) |
C3C—C4C—N41C—O41C | −12.0 (5) | C3G—C4G—N41G—O41G | 6.2 (6) |
C5C—C4C—N41C—O41C | 168.2 (3) | C5G—C4G—N41G—O41G | −175.0 (4) |
C3C—C4C—C5C—C6C | 1.1 (5) | C3G—C4G—C5G—C6G | 0.5 (6) |
N41C—C4C—C5C—C6C | −179.2 (3) | N41G—C4G—C5G—C6G | −178.3 (3) |
C2C—C1C—C6C—C5C | 0.2 (5) | C2G—C1G—C6G—C5G | 0.2 (5) |
C11C—C1C—C6C—C5C | −178.7 (3) | C11G—C1G—C6G—C5G | 179.2 (3) |
C4C—C5C—C6C—C1C | −1.3 (5) | C4G—C5G—C6G—C1G | −0.6 (6) |
C6D—C1D—C11D—O11D | 0.4 (5) | C2H—C1H—C11H—O10H | 3.1 (8) |
C2D—C1D—C11D—O11D | −179.6 (3) | C6H—C1H—C11H—O10H | −176.7 (5) |
C6D—C1D—C11D—O10D | −179.2 (3) | C2H—C1H—C11H—O11H | −175.7 (5) |
C2D—C1D—C11D—O10D | 0.9 (5) | C6H—C1H—C11H—O11H | 4.5 (7) |
C6D—C1D—C2D—C3D | 1.2 (5) | C6H—C1H—C2H—C3H | −1.7 (6) |
C11D—C1D—C2D—C3D | −178.9 (3) | C11H—C1H—C2H—C3H | 178.5 (4) |
C1D—C2D—C3D—C4D | −1.5 (5) | C1H—C2H—C3H—C4H | 1.0 (7) |
C2D—C3D—C4D—C5D | 0.6 (5) | C2H—C3H—C4H—C5H | 0.5 (6) |
C2D—C3D—C4D—N41D | −179.3 (3) | C2H—C3H—C4H—N41H | −177.9 (4) |
C5D—C4D—N41D—O41D | 178.4 (3) | C5H—C4H—N41H—O42H | −2.0 (6) |
C3D—C4D—N41D—O41D | −1.7 (5) | C3H—C4H—N41H—O42H | 176.4 (4) |
C5D—C4D—N41D—O42D | −1.1 (5) | C5H—C4H—N41H—O41H | 178.1 (4) |
C3D—C4D—N41D—O42D | 178.8 (3) | C3H—C4H—N41H—O41H | −3.4 (6) |
C3D—C4D—C5D—C6D | 0.7 (5) | C3H—C4H—C5H—C6H | −1.1 (6) |
N41D—C4D—C5D—C6D | −179.4 (3) | N41H—C4H—C5H—C6H | 177.2 (3) |
C4D—C5D—C6D—C1D | −1.1 (5) | C4H—C5H—C6H—C1H | 0.4 (6) |
C2D—C1D—C6D—C5D | 0.2 (5) | C2H—C1H—C6H—C5H | 1.1 (6) |
C11D—C1D—C6D—C5D | −179.7 (3) | C11H—C1H—C6H—C5H | −179.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4A—H41A···O11Ci | 0.89 | 1.91 | 2.787 (4) | 168 |
N4A—H42A···O10Bi | 0.89 | 2.30 | 2.938 (4) | 128 |
N4A—H42A···O11Bi | 0.89 | 2.37 | 3.086 (4) | 137 |
N4A—H42A···O10Cii | 0.89 | 2.63 | 3.130 (5) | 116 |
N4A—H43A···O11Bii | 0.89 | 1.98 | 2.839 (4) | 162 |
N7A—H71A···O11Ci | 0.89 | 1.85 | 2.703 (5) | 161 |
N7A—H72A···O1Wiii | 0.89 | 1.91 | 2.748 (4) | 156 |
N7A—H73A···O42W | 0.89 | 1.68 | 2.495 (11) | 151 |
N7A—H73A···O41W | 0.89 | 2.23 | 3.119 (8) | 173 |
N10A—H11A···O10Fi | 0.89 | 2.18 | 3.061 (4) | 169 |
N10A—H11A···O11Fi | 0.89 | 2.27 | 2.902 (4) | 128 |
N10A—H12A···O10Ci | 0.89 | 2.50 | 3.162 (5) | 132 |
N10A—H12A···O11Bii | 0.89 | 2.53 | 2.995 (4) | 114 |
N10A—H13A···O11Dii | 0.89 | 2.01 | 2.841 (4) | 155 |
N4E—H41E···O2W | 0.89 | 1.98 | 2.815 (5) | 156 |
N4E—H42E···O10Di | 0.89 | 1.98 | 2.849 (3) | 164 |
N4E—H43E···O11Fiv | 0.89 | 2.30 | 2.968 (4) | 132 |
N4E—H43E···O11Fii | 0.89 | 2.48 | 3.017 (4) | 119 |
N7E—H71E···O10Fiv | 0.89 | 2.03 | 2.873 (4) | 157 |
N7E—H72E···O10Di | 0.89 | 1.98 | 2.838 (3) | 162 |
N7E—H73E···O11Gi | 0.89 | 1.90 | 2.742 (4) | 158 |
N10E—H11E···O10Di | 0.89 | 2.01 | 2.859 (4) | 160 |
N10E—H12E···O10Bi | 0.89 | 1.88 | 2.734 (4) | 159 |
N10E—H13E···O3Wiii | 0.89 | 1.86 | 2.733 (5) | 166 |
O1W—H11···O10Gv | 0.81 (3) | 1.92 (3) | 2.722 (4) | 171 (4) |
O1W—H12···O11Gi | 0.81 (2) | 2.02 (3) | 2.805 (4) | 166 (5) |
O2W—H21···O10Cii | 0.80 (5) | 2.03 (4) | 2.625 (4) | 129 (4) |
O2W—H22···O10Bi | 0.81 (3) | 2.19 (2) | 2.943 (5) | 154 (5) |
O3W—H31···O10H | 0.82 (5) | 2.03 (3) | 2.812 (6) | 177 (7) |
O3W—H32···O11Hiii | 0.82 (5) | 2.03 (5) | 2.821 (6) | 163 (5) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) x−1, y−1, z; (v) −x+1, −y, −z+1. |