The creation of ternary multi-component crystals through the introduction of 18-crown-6 to direct the hydrogen-bonding motifs of the other molecular components was investigated for 3,5-dinitrobenzoic acid (3,5-dnba) with 4-aminobenzoic acid (4-aba). The creation of a binary complex between 18-crown-6 and 4-aba (C
12H
24O
6·2C
7H
7NO
2)
2 and a ternary salt between 3,5-dnba, 18-crown-6 and 4-aba (C
12H
24O
6·C
7H
8NO
2+·C
7H
3N
2O
6−·C
7H
4N
2O
6) were confirmed by single-crystal structure determination. In both structures, the amino molecules bind to the crown ether through N—H
O hydrogen bonds, leaving available only a single O atom site on the crown with restricted geometry to potentially accept a hydrogen bond from 3,5-dnba. While 3,5-dnba and 4-aba form a binary co-crystal containing neutral molecules, the shape-selective nature of 18-crown-6 preferentially binds protonated amino molecules, thereby leading to the formation of the ternary salt, despite the predicted low concentration of the protonated species in the crystallizing solution. Thus, through the choice of crown ether it may be possible to control both location and nature of the available bonding sites for the designed creation of ternary crystals.
Supporting information
CCDC references: 962492; 962493
For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2005) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013.
(1) 18-crown-6/bis(4-aminobenzoic acid)
top
Crystal data top
C12H24O6·2(C7H7NO2) | F(000) = 3456 |
Mr = 538.58 | Dx = 1.245 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3947 (3) Å | Cell parameters from 9698 reflections |
b = 17.5546 (5) Å | θ = 2.3–23.3° |
c = 47.2700 (14) Å | µ = 0.10 mm−1 |
β = 91.321 (2)° | T = 173 K |
V = 8623.3 (4) Å3 | Block, colourless |
Z = 12 | 0.79 × 0.65 × 0.53 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 10452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 26.1°, θmin = 1.7° |
Absorption correction: multi-scan SADABS (Bruker, 2008) | h = −12→11 |
Tmin = 0.928, Tmax = 0.950 | k = −20→21 |
132140 measured reflections | l = −58→52 |
16030 independent reflections | |
Refinement top
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.199 | w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
16030 reflections | Δρmax = 0.91 e Å−3 |
1114 parameters | Δρmin = −0.37 e Å−3 |
Crystal data top
C12H24O6·2(C7H7NO2) | V = 8623.3 (4) Å3 |
Mr = 538.58 | Z = 12 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.3947 (3) Å | µ = 0.10 mm−1 |
b = 17.5546 (5) Å | T = 173 K |
c = 47.2700 (14) Å | 0.79 × 0.65 × 0.53 mm |
β = 91.321 (2)° | |
Data collection top
Bruker APEX-II CCD diffractometer | 16030 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2008) | 10452 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 0.950 | Rint = 0.045 |
132140 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.073 | 6 restraints |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P] where P = (Fo2 + 2Fc2)/3 |
16030 reflections | Δρmax = 0.91 e Å−3 |
1114 parameters | Δρmin = −0.37 e Å−3 |
Special details top
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. One section of one crown ether is refined as disordered over two positions. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.7184 (3) | 0.32762 (18) | 0.01502 (6) | 0.0626 (8) | |
O2AA | 0.4540 (6) | 0.3599 (4) | 0.02787 (16) | 0.0631 (18) | 0.673 (12) |
O2AB | 0.4614 (8) | 0.3883 (6) | 0.0153 (2) | 0.033 (3) | 0.327 (12) |
O3A | 0.2490 (3) | 0.26694 (15) | 0.00704 (6) | 0.0495 (7) | |
O4A | 0.3506 (2) | 0.16745 (14) | −0.03292 (5) | 0.0430 (6) | |
O5A | 0.5925 (2) | 0.11338 (14) | −0.04352 (5) | 0.0413 (6) | |
O6A | 0.7895 (2) | 0.18617 (15) | −0.00732 (5) | 0.0421 (6) | |
C1A | 0.8751 (4) | 0.2487 (3) | −0.00409 (8) | 0.0508 (11) | |
H1AA | 0.8706 | 0.2811 | −0.0212 | 0.061* | |
H1AB | 0.9644 | 0.2299 | −0.0017 | 0.061* | |
C2A | 0.8391 (4) | 0.2939 (3) | 0.02100 (9) | 0.0524 (11) | |
H2AA | 0.8339 | 0.2605 | 0.0378 | 0.063* | |
H2AB | 0.9045 | 0.3337 | 0.0250 | 0.063* | |
C3A | 0.6734 (5) | 0.3715 (3) | 0.03805 (11) | 0.0754 (15) | |
H3AA | 0.7415 | 0.4066 | 0.0451 | 0.090* | 0.673 (12) |
H3AB | 0.6486 | 0.3377 | 0.0538 | 0.090* | 0.673 (12) |
H3AC | 0.6879 | 0.4262 | 0.0342 | 0.090* | 0.327 (12) |
H3AD | 0.7235 | 0.3580 | 0.0554 | 0.090* | 0.327 (12) |
C4AA | 0.5612 (7) | 0.4147 (4) | 0.02741 (15) | 0.062 (2) | 0.673 (12) |
H4AA | 0.5752 | 0.4332 | 0.0079 | 0.075* | 0.673 (12) |
H4AB | 0.5440 | 0.4589 | 0.0398 | 0.075* | 0.673 (12) |
C4AB | 0.5076 (16) | 0.3562 (9) | 0.0440 (4) | 0.062 (5) | 0.327 (12) |
H4AC | 0.4861 | 0.3016 | 0.0463 | 0.075* | 0.327 (12) |
H4AD | 0.4758 | 0.3860 | 0.0602 | 0.075* | 0.327 (12) |
C5A | 0.3350 (6) | 0.3925 (4) | 0.01860 (15) | 0.098 (2) | |
H5AA | 0.3377 | 0.4060 | −0.0017 | 0.118* | 0.673 (12) |
H5AB | 0.3161 | 0.4390 | 0.0296 | 0.118* | 0.673 (12) |
H5AC | 0.3031 | 0.4200 | 0.0015 | 0.118* | 0.327 (12) |
H5AD | 0.3250 | 0.4285 | 0.0345 | 0.118* | 0.327 (12) |
C6A | 0.2381 (4) | 0.3344 (3) | 0.02331 (10) | 0.0595 (12) | |
H6AA | 0.2417 | 0.3203 | 0.0436 | 0.071* | |
H6AB | 0.1524 | 0.3570 | 0.0193 | 0.071* | |
C7A | 0.2310 (4) | 0.2783 (2) | −0.02255 (9) | 0.0513 (11) | |
H7AA | 0.3018 | 0.3099 | −0.0298 | 0.062* | |
H7AB | 0.1489 | 0.3053 | −0.0263 | 0.062* | |
C8A | 0.2290 (4) | 0.2028 (2) | −0.03715 (8) | 0.0478 (10) | |
H8AA | 0.1605 | 0.1703 | −0.0293 | 0.057* | |
H8AB | 0.2109 | 0.2098 | −0.0576 | 0.057* | |
C9A | 0.3656 (4) | 0.0992 (2) | −0.04863 (9) | 0.0491 (10) | |
H9AA | 0.3679 | 0.1109 | −0.0691 | 0.059* | |
H9AB | 0.2923 | 0.0646 | −0.0454 | 0.059* | |
C10A | 0.4888 (4) | 0.0621 (2) | −0.03917 (9) | 0.0488 (10) | |
H10A | 0.4849 | 0.0486 | −0.0189 | 0.059* | |
H10B | 0.5022 | 0.0147 | −0.0501 | 0.059* | |
C11A | 0.7140 (4) | 0.0823 (3) | −0.03506 (8) | 0.0526 (11) | |
H11A | 0.7418 | 0.0443 | −0.0492 | 0.063* | |
H11B | 0.7068 | 0.0563 | −0.0166 | 0.063* | |
C12A | 0.8108 (4) | 0.1449 (3) | −0.03271 (8) | 0.0508 (11) | |
H12A | 0.8989 | 0.1233 | −0.0323 | 0.061* | |
H12B | 0.8022 | 0.1793 | −0.0492 | 0.061* | |
O1B | 0.0630 (3) | 0.08359 (15) | 0.01362 (6) | 0.0453 (7) | |
H1B | 0.067 (5) | 0.053 (3) | −0.0051 (12) | 0.108 (19)* | |
O2B | −0.0586 (3) | −0.00576 (15) | 0.03328 (6) | 0.0542 (7) | |
C1B | 0.0039 (3) | 0.0566 (2) | 0.03489 (8) | 0.0366 (8) | |
C2B | 0.0107 (3) | 0.09804 (19) | 0.06156 (7) | 0.0325 (8) | |
C3B | −0.0349 (4) | 0.0665 (2) | 0.08643 (8) | 0.0428 (9) | |
H3B | −0.0753 | 0.0180 | 0.0856 | 0.051* | |
C4B | −0.0236 (4) | 0.1030 (2) | 0.11202 (8) | 0.0416 (9) | |
H4B | −0.0543 | 0.0794 | 0.1286 | 0.050* | |
C5B | 0.0334 (3) | 0.1756 (2) | 0.11355 (7) | 0.0350 (8) | |
C6B | 0.0779 (3) | 0.2083 (2) | 0.08843 (7) | 0.0357 (8) | |
H6B | 0.1156 | 0.2576 | 0.0890 | 0.043* | |
C7B | 0.0676 (3) | 0.17028 (19) | 0.06311 (7) | 0.0333 (8) | |
H7B | 0.0995 | 0.1932 | 0.0465 | 0.040* | |
N1B | 0.0484 (4) | 0.2125 (2) | 0.13838 (8) | 0.0469 (9) | |
H1BA | 0.008 (4) | 0.198 (3) | 0.1528 (10) | 0.066 (15)* | |
H1BB | 0.080 (5) | 0.258 (3) | 0.1378 (11) | 0.082 (18)* | |
O1C | 0.5843 (3) | 0.48121 (14) | 0.13538 (5) | 0.0444 (7) | |
H1C | 0.596 (5) | 0.459 (3) | 0.1550 (11) | 0.098 (17)* | |
O2C | 0.6327 (3) | 0.59009 (15) | 0.15738 (5) | 0.0460 (7) | |
C1C | 0.5960 (3) | 0.5554 (2) | 0.13580 (7) | 0.0321 (8) | |
C2C | 0.5595 (3) | 0.59509 (19) | 0.10972 (7) | 0.0284 (7) | |
C3C | 0.5677 (3) | 0.67427 (19) | 0.10832 (7) | 0.0330 (8) | |
H3C | 0.6021 | 0.7018 | 0.1241 | 0.040* | |
C4C | 0.5268 (3) | 0.7131 (2) | 0.08465 (7) | 0.0342 (8) | |
H4C | 0.5347 | 0.7669 | 0.0841 | 0.041* | |
C5C | 0.4735 (3) | 0.6747 (2) | 0.06118 (7) | 0.0339 (8) | |
C6C | 0.4685 (4) | 0.5952 (2) | 0.06250 (7) | 0.0407 (9) | |
H6C | 0.4353 | 0.5674 | 0.0467 | 0.049* | |
C7C | 0.5108 (4) | 0.5566 (2) | 0.08624 (7) | 0.0376 (8) | |
H7C | 0.5065 | 0.5026 | 0.0865 | 0.045* | |
N1C | 0.4246 (4) | 0.7134 (3) | 0.03864 (8) | 0.0468 (9) | |
H1CA | 0.436 (4) | 0.760 (3) | 0.0390 (9) | 0.055 (14)* | |
H1CB | 0.403 (5) | 0.690 (3) | 0.0245 (11) | 0.077 (18)* | |
O1D | 0.5960 (2) | 0.53383 (14) | 0.20783 (5) | 0.0424 (6) | |
H1D | 0.6134 | 0.5489 | 0.1915 | 0.064* | |
O2D | 0.5878 (3) | 0.42146 (14) | 0.18572 (5) | 0.0418 (6) | |
C1D | 0.5725 (3) | 0.4601 (2) | 0.20724 (7) | 0.0316 (8) | |
C2D | 0.5276 (3) | 0.42663 (19) | 0.23337 (7) | 0.0289 (7) | |
C3D | 0.5112 (3) | 0.4690 (2) | 0.25803 (7) | 0.0332 (8) | |
H3D | 0.5314 | 0.5217 | 0.2581 | 0.040* | |
C4D | 0.4665 (3) | 0.4358 (2) | 0.28221 (7) | 0.0365 (8) | |
H4D | 0.4577 | 0.4657 | 0.2988 | 0.044* | |
C5D | 0.4336 (3) | 0.3580 (2) | 0.28263 (7) | 0.0318 (8) | |
C6D | 0.4501 (3) | 0.3159 (2) | 0.25777 (7) | 0.0343 (8) | |
H6D | 0.4293 | 0.2632 | 0.2576 | 0.041* | |
C7D | 0.4956 (3) | 0.34900 (19) | 0.23380 (7) | 0.0318 (8) | |
H7D | 0.5056 | 0.3191 | 0.2172 | 0.038* | |
N1D | 0.3863 (3) | 0.3245 (2) | 0.30573 (8) | 0.0457 (8) | |
H1DA | 0.380 (5) | 0.348 (3) | 0.3214 (11) | 0.078 (17)* | |
H1DB | 0.380 (4) | 0.275 (3) | 0.3063 (10) | 0.069 (16)* | |
O1E | 0.1113 (2) | 0.54213 (16) | 0.02265 (5) | 0.0458 (7) | |
H1E | 0.098 (6) | 0.515 (4) | 0.0013 (14) | 0.13 (2)* | |
O2E | −0.1001 (2) | 0.52463 (16) | 0.02695 (5) | 0.0447 (6) | |
C1E | 0.0067 (3) | 0.55030 (19) | 0.03627 (7) | 0.0318 (8) | |
C2E | 0.0144 (3) | 0.59040 (18) | 0.06338 (6) | 0.0286 (7) | |
C3E | −0.0943 (3) | 0.60271 (19) | 0.07964 (7) | 0.0304 (7) | |
H3E | −0.1760 | 0.5859 | 0.0727 | 0.036* | |
C4E | −0.0853 (3) | 0.63853 (19) | 0.10529 (7) | 0.0317 (8) | |
H4E | −0.1607 | 0.6464 | 0.1159 | 0.038* | |
C5E | 0.0348 (3) | 0.66386 (19) | 0.11615 (7) | 0.0328 (8) | |
C6E | 0.1436 (3) | 0.6526 (2) | 0.09947 (7) | 0.0351 (8) | |
H6E | 0.2252 | 0.6703 | 0.1061 | 0.042* | |
C7E | 0.1332 (3) | 0.6166 (2) | 0.07391 (7) | 0.0334 (8) | |
H7E | 0.2081 | 0.6091 | 0.0631 | 0.040* | |
N1E | 0.0442 (4) | 0.6984 (2) | 0.14163 (7) | 0.0463 (9) | |
H1EA | −0.023 (4) | 0.709 (2) | 0.1523 (8) | 0.043 (11)* | |
H1EB | 0.119 (4) | 0.712 (2) | 0.1450 (9) | 0.053 (14)* | |
O1F | −0.1069 (3) | 0.49496 (18) | 0.30440 (6) | 0.0562 (8) | |
H1F | −0.101 (6) | 0.513 (4) | 0.3282 (15) | 0.15 (3)* | |
O2F | 0.1069 (3) | 0.48524 (16) | 0.30858 (5) | 0.0502 (7) | |
C1F | 0.0025 (4) | 0.4764 (2) | 0.29457 (7) | 0.0348 (8) | |
C2F | 0.0066 (3) | 0.44390 (19) | 0.26603 (7) | 0.0323 (8) | |
C3F | 0.1245 (3) | 0.4240 (2) | 0.25453 (7) | 0.0355 (8) | |
H3F | 0.2016 | 0.4312 | 0.2654 | 0.043* | |
C4F | 0.1302 (3) | 0.3943 (2) | 0.22782 (7) | 0.0370 (8) | |
H4F | 0.2113 | 0.3809 | 0.2204 | 0.044* | |
C5F | 0.0181 (3) | 0.38328 (19) | 0.21126 (7) | 0.0324 (8) | |
C6F | −0.1004 (3) | 0.4017 (2) | 0.22307 (7) | 0.0358 (8) | |
H6F | −0.1778 | 0.3934 | 0.2125 | 0.043* | |
C7F | −0.1055 (3) | 0.4316 (2) | 0.24980 (7) | 0.0355 (8) | |
H7F | −0.1865 | 0.4441 | 0.2574 | 0.043* | |
N1F | 0.0247 (4) | 0.3561 (2) | 0.18454 (7) | 0.0485 (9) | |
H1FA | 0.100 (4) | 0.343 (2) | 0.1789 (8) | 0.049 (12)* | |
H1FB | −0.043 (5) | 0.343 (3) | 0.1779 (11) | 0.09 (2)* | |
O1G | 0.1069 (3) | 0.54242 (16) | 0.35941 (5) | 0.0468 (7) | |
H1G | 0.104 (7) | 0.514 (4) | 0.3351 (15) | 0.15 (3)* | |
O2G | −0.1076 (3) | 0.54402 (18) | 0.35628 (5) | 0.0544 (8) | |
C1G | −0.0024 (4) | 0.5568 (2) | 0.36977 (7) | 0.0360 (8) | |
C2G | −0.0075 (3) | 0.58889 (19) | 0.39831 (7) | 0.0324 (8) | |
C3G | 0.1047 (3) | 0.6076 (2) | 0.41375 (7) | 0.0371 (8) | |
H3G | 0.1862 | 0.5998 | 0.4055 | 0.044* | |
C4G | 0.0983 (3) | 0.6367 (2) | 0.44044 (7) | 0.0380 (9) | |
H4G | 0.1756 | 0.6493 | 0.4505 | 0.046* | |
C5G | −0.0206 (3) | 0.6485 (2) | 0.45334 (7) | 0.0333 (8) | |
C6G | −0.1334 (3) | 0.6301 (2) | 0.43786 (7) | 0.0369 (8) | |
H6G | −0.2150 | 0.6375 | 0.4461 | 0.044* | |
C7G | −0.1259 (4) | 0.6015 (2) | 0.41087 (7) | 0.0381 (8) | |
H7G | −0.2029 | 0.5900 | 0.4005 | 0.046* | |
N1G | −0.0261 (4) | 0.6741 (2) | 0.48016 (7) | 0.0463 (9) | |
H1GA | −0.097 (4) | 0.684 (2) | 0.4871 (8) | 0.034 (10)* | |
H1GB | 0.040 (5) | 0.690 (3) | 0.4882 (10) | 0.064 (15)* | |
O1H | −0.1057 (2) | 0.69527 (14) | 0.19681 (5) | 0.0429 (6) | |
O2H | −0.2243 (3) | 0.79586 (16) | 0.16004 (6) | 0.0548 (7) | |
O3H | −0.0290 (3) | 0.88757 (17) | 0.12848 (6) | 0.0530 (7) | |
O4H | 0.2292 (3) | 0.8539 (2) | 0.13866 (6) | 0.0755 (11) | |
O5H | 0.3219 (2) | 0.72479 (15) | 0.16639 (5) | 0.0454 (6) | |
O6H | 0.1463 (2) | 0.64817 (14) | 0.20415 (6) | 0.0463 (7) | |
C1H | 0.0434 (4) | 0.5947 (2) | 0.20215 (10) | 0.0545 (11) | |
H1HA | 0.0657 | 0.5485 | 0.2132 | 0.065* | |
H1HB | 0.0290 | 0.5794 | 0.1822 | 0.065* | |
C2H | −0.0766 (4) | 0.6299 (2) | 0.21331 (9) | 0.0511 (10) | |
H2HA | −0.1486 | 0.5931 | 0.2120 | 0.061* | |
H2HB | −0.0631 | 0.6444 | 0.2334 | 0.061* | |
C3H | −0.2276 (4) | 0.7264 (3) | 0.20270 (8) | 0.0494 (10) | |
H3HA | −0.2374 | 0.7309 | 0.2234 | 0.059* | |
H3HB | −0.2963 | 0.6924 | 0.1952 | 0.059* | |
C4H | −0.2397 (4) | 0.8021 (2) | 0.18945 (9) | 0.0524 (11) | |
H4HA | −0.3254 | 0.8239 | 0.1933 | 0.063* | |
H4HB | −0.1734 | 0.8368 | 0.1976 | 0.063* | |
C5H | −0.2384 (5) | 0.8670 (3) | 0.14570 (13) | 0.0830 (18) | |
H5HA | −0.2131 | 0.9090 | 0.1587 | 0.100* | |
H5HB | −0.3297 | 0.8745 | 0.1400 | 0.100* | |
C6H | −0.1588 (5) | 0.8691 (3) | 0.12079 (11) | 0.0767 (16) | |
H6HA | −0.1615 | 0.8188 | 0.1113 | 0.092* | |
H6HB | −0.1932 | 0.9076 | 0.1073 | 0.092* | |
C7H | 0.0563 (5) | 0.8736 (3) | 0.10630 (9) | 0.0643 (13) | |
H7HA | 0.0277 | 0.9019 | 0.0892 | 0.077* | |
H7HB | 0.0567 | 0.8186 | 0.1017 | 0.077* | |
C8H | 0.1855 (5) | 0.8980 (4) | 0.11489 (10) | 0.0795 (17) | |
H8HA | 0.2448 | 0.8911 | 0.0990 | 0.095* | |
H8HB | 0.1846 | 0.9526 | 0.1200 | 0.095* | |
C9H | 0.3578 (4) | 0.8338 (3) | 0.13787 (9) | 0.0537 (11) | |
H9HA | 0.4112 | 0.8801 | 0.1360 | 0.064* | |
H9HB | 0.3725 | 0.8009 | 0.1213 | 0.064* | |
C10H | 0.3955 (4) | 0.7924 (2) | 0.16425 (10) | 0.0534 (11) | |
H10C | 0.4882 | 0.7796 | 0.1640 | 0.064* | |
H10D | 0.3806 | 0.8253 | 0.1809 | 0.064* | |
C11H | 0.3578 (4) | 0.6813 (3) | 0.19072 (10) | 0.0583 (12) | |
H11C | 0.3589 | 0.7143 | 0.2077 | 0.070* | |
H11D | 0.4453 | 0.6601 | 0.1885 | 0.070* | |
C12H | 0.2637 (4) | 0.6181 (3) | 0.19429 (11) | 0.0608 (12) | |
H12C | 0.2484 | 0.5919 | 0.1760 | 0.073* | |
H12D | 0.2987 | 0.5804 | 0.2080 | 0.073* | |
O1I | −0.2089 (3) | 0.32047 (18) | 0.14245 (6) | 0.0626 (8) | |
O2I | 0.0163 (3) | 0.38849 (18) | 0.11605 (6) | 0.0677 (9) | |
O3I | 0.2408 (3) | 0.3445 (2) | 0.14116 (7) | 0.0704 (9) | |
O4I | 0.2851 (3) | 0.2409 (2) | 0.18463 (7) | 0.0709 (9) | |
O5I | 0.0579 (3) | 0.15949 (18) | 0.20840 (6) | 0.0659 (9) | |
O6I | −0.1647 (3) | 0.21133 (19) | 0.18431 (7) | 0.0673 (9) | |
C1I | −0.2873 (4) | 0.2230 (3) | 0.17292 (11) | 0.0690 (14) | |
H1IA | −0.3331 | 0.2614 | 0.1842 | 0.083* | |
H1IB | −0.3368 | 0.1749 | 0.1733 | 0.083* | |
C2I | −0.2769 (4) | 0.2496 (3) | 0.14368 (10) | 0.0597 (12) | |
H2IA | −0.2312 | 0.2108 | 0.1325 | 0.072* | |
H2IB | −0.3641 | 0.2561 | 0.1352 | 0.072* | |
C3I | −0.2031 (5) | 0.3491 (3) | 0.11502 (10) | 0.0699 (14) | |
H3IA | −0.2897 | 0.3660 | 0.1085 | 0.084* | |
H3IB | −0.1735 | 0.3088 | 0.1020 | 0.084* | |
C4I | −0.1133 (5) | 0.4137 (3) | 0.11480 (10) | 0.0666 (13) | |
H4IA | −0.1283 | 0.4438 | 0.0973 | 0.080* | |
H4IB | −0.1296 | 0.4471 | 0.1312 | 0.080* | |
C5I | 0.1040 (6) | 0.4438 (3) | 0.12364 (11) | 0.0807 (16) | |
H5IA | 0.0845 | 0.4637 | 0.1427 | 0.097* | |
H5IB | 0.0986 | 0.4866 | 0.1100 | 0.097* | |
C6I | 0.2382 (5) | 0.4103 (3) | 0.12387 (12) | 0.0797 (16) | |
H6IA | 0.2623 | 0.3967 | 0.1044 | 0.096* | |
H6IB | 0.3009 | 0.4481 | 0.1313 | 0.096* | |
C7I | 0.3624 (5) | 0.3160 (4) | 0.14617 (13) | 0.0912 (19) | |
H7IA | 0.4109 | 0.3503 | 0.1592 | 0.109* | |
H7IB | 0.4092 | 0.3130 | 0.1282 | 0.109* | |
C8I | 0.3523 (4) | 0.2362 (3) | 0.15938 (11) | 0.0705 (14) | |
H8IA | 0.3068 | 0.2015 | 0.1460 | 0.085* | |
H8IB | 0.4396 | 0.2155 | 0.1632 | 0.085* | |
C9I | 0.2810 (5) | 0.1706 (3) | 0.19820 (13) | 0.0807 (16) | |
H9IA | 0.3674 | 0.1583 | 0.2062 | 0.097* | |
H9IB | 0.2572 | 0.1306 | 0.1843 | 0.097* | |
C10I | 0.1863 (5) | 0.1709 (3) | 0.22133 (11) | 0.0732 (14) | |
H10E | 0.2061 | 0.1295 | 0.2350 | 0.088* | |
H10F | 0.1898 | 0.2200 | 0.2316 | 0.088* | |
C11I | −0.0367 (5) | 0.1843 (3) | 0.22582 (9) | 0.0655 (13) | |
H11E | −0.0240 | 0.2389 | 0.2303 | 0.079* | |
H11F | −0.0337 | 0.1552 | 0.2438 | 0.079* | |
C12I | −0.1633 (5) | 0.1728 (3) | 0.21100 (9) | 0.0673 (13) | |
H12E | −0.1785 | 0.1177 | 0.2080 | 0.081* | |
H12F | −0.2330 | 0.1928 | 0.2228 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0495 (18) | 0.072 (2) | 0.0654 (19) | 0.0156 (16) | −0.0255 (15) | −0.0180 (16) |
O2AA | 0.064 (4) | 0.050 (4) | 0.074 (5) | 0.017 (3) | −0.030 (3) | 0.004 (3) |
O2AB | 0.020 (5) | 0.035 (6) | 0.043 (6) | 0.016 (4) | −0.002 (4) | 0.005 (4) |
O3A | 0.0503 (17) | 0.0474 (16) | 0.0510 (16) | 0.0024 (13) | 0.0043 (13) | 0.0105 (13) |
O4A | 0.0350 (14) | 0.0438 (15) | 0.0501 (15) | 0.0017 (12) | −0.0043 (12) | 0.0008 (12) |
O5A | 0.0420 (15) | 0.0454 (15) | 0.0363 (13) | 0.0080 (12) | −0.0007 (11) | 0.0040 (11) |
O6A | 0.0333 (14) | 0.0577 (17) | 0.0355 (14) | 0.0024 (12) | 0.0039 (11) | 0.0058 (12) |
C1A | 0.035 (2) | 0.069 (3) | 0.048 (2) | −0.003 (2) | −0.0021 (18) | 0.017 (2) |
C2A | 0.039 (2) | 0.059 (3) | 0.058 (3) | −0.008 (2) | −0.016 (2) | 0.010 (2) |
C3A | 0.067 (3) | 0.079 (4) | 0.079 (3) | 0.010 (3) | −0.032 (3) | −0.035 (3) |
C4AA | 0.071 (5) | 0.055 (4) | 0.061 (4) | 0.010 (3) | −0.009 (4) | −0.021 (3) |
C4AB | 0.072 (11) | 0.059 (9) | 0.055 (8) | 0.034 (8) | 0.003 (6) | −0.004 (6) |
C5A | 0.078 (4) | 0.086 (4) | 0.131 (5) | 0.001 (3) | 0.019 (4) | −0.031 (4) |
C6A | 0.052 (3) | 0.059 (3) | 0.069 (3) | 0.008 (2) | 0.015 (2) | 0.001 (2) |
C7A | 0.038 (2) | 0.058 (3) | 0.059 (3) | 0.0141 (19) | 0.0140 (19) | 0.022 (2) |
C8A | 0.032 (2) | 0.070 (3) | 0.041 (2) | 0.005 (2) | 0.0011 (17) | 0.013 (2) |
C9A | 0.052 (2) | 0.047 (2) | 0.048 (2) | −0.008 (2) | −0.0042 (19) | −0.0027 (19) |
C10A | 0.057 (3) | 0.039 (2) | 0.051 (2) | 0.003 (2) | 0.001 (2) | −0.0011 (18) |
C11A | 0.056 (3) | 0.061 (3) | 0.041 (2) | 0.024 (2) | 0.0021 (19) | −0.001 (2) |
C12A | 0.041 (2) | 0.075 (3) | 0.036 (2) | 0.017 (2) | 0.0073 (17) | 0.007 (2) |
O1B | 0.0568 (17) | 0.0402 (15) | 0.0389 (15) | −0.0042 (13) | 0.0045 (13) | −0.0062 (12) |
O2B | 0.0656 (19) | 0.0399 (16) | 0.0577 (18) | −0.0170 (14) | 0.0147 (14) | −0.0182 (13) |
C1B | 0.0314 (19) | 0.032 (2) | 0.047 (2) | 0.0008 (16) | 0.0030 (16) | −0.0071 (17) |
C2B | 0.0271 (18) | 0.0298 (18) | 0.040 (2) | 0.0028 (15) | 0.0010 (15) | −0.0085 (15) |
C3B | 0.044 (2) | 0.033 (2) | 0.053 (2) | −0.0052 (17) | 0.0134 (18) | −0.0092 (17) |
C4B | 0.043 (2) | 0.038 (2) | 0.045 (2) | −0.0027 (17) | 0.0156 (17) | −0.0053 (17) |
C5B | 0.0236 (18) | 0.041 (2) | 0.041 (2) | 0.0041 (15) | 0.0045 (15) | −0.0087 (17) |
C6B | 0.0302 (19) | 0.0326 (19) | 0.044 (2) | −0.0025 (15) | −0.0017 (16) | −0.0081 (16) |
C7B | 0.0263 (18) | 0.0336 (19) | 0.040 (2) | 0.0044 (15) | −0.0016 (15) | 0.0019 (16) |
N1B | 0.048 (2) | 0.052 (2) | 0.041 (2) | −0.0063 (18) | 0.0042 (16) | −0.0120 (17) |
O1C | 0.0718 (19) | 0.0329 (15) | 0.0282 (13) | 0.0018 (13) | −0.0024 (12) | 0.0086 (11) |
O2C | 0.0631 (18) | 0.0458 (15) | 0.0286 (13) | −0.0165 (13) | −0.0076 (12) | 0.0062 (12) |
C1C | 0.0327 (19) | 0.034 (2) | 0.0294 (18) | −0.0024 (15) | 0.0020 (15) | 0.0055 (15) |
C2C | 0.0251 (17) | 0.0336 (19) | 0.0266 (17) | −0.0013 (14) | 0.0012 (13) | 0.0048 (14) |
C3C | 0.040 (2) | 0.036 (2) | 0.0234 (16) | −0.0047 (16) | 0.0040 (14) | 0.0014 (15) |
C4C | 0.042 (2) | 0.0324 (19) | 0.0290 (18) | 0.0010 (16) | 0.0093 (15) | 0.0047 (15) |
C5C | 0.0247 (18) | 0.045 (2) | 0.0317 (18) | −0.0019 (16) | 0.0022 (14) | 0.0145 (16) |
C6C | 0.051 (2) | 0.043 (2) | 0.0276 (18) | −0.0117 (18) | −0.0093 (16) | 0.0026 (16) |
C7C | 0.050 (2) | 0.0320 (19) | 0.0305 (18) | −0.0075 (17) | −0.0033 (16) | 0.0055 (15) |
N1C | 0.050 (2) | 0.049 (2) | 0.041 (2) | −0.0048 (18) | −0.0130 (16) | 0.0170 (18) |
O1D | 0.0579 (17) | 0.0352 (14) | 0.0340 (13) | −0.0119 (12) | −0.0008 (12) | 0.0104 (11) |
O2D | 0.0603 (17) | 0.0389 (14) | 0.0264 (13) | 0.0006 (12) | 0.0051 (11) | 0.0069 (11) |
C1D | 0.0299 (19) | 0.036 (2) | 0.0289 (18) | 0.0012 (15) | −0.0033 (14) | 0.0055 (15) |
C2D | 0.0247 (17) | 0.0312 (18) | 0.0308 (17) | 0.0007 (14) | −0.0034 (14) | 0.0045 (14) |
C3D | 0.037 (2) | 0.0284 (18) | 0.0338 (18) | −0.0017 (15) | −0.0011 (15) | 0.0024 (15) |
C4D | 0.040 (2) | 0.040 (2) | 0.0298 (18) | 0.0021 (17) | 0.0053 (15) | 0.0016 (16) |
C5D | 0.0246 (17) | 0.041 (2) | 0.0302 (18) | 0.0025 (15) | 0.0013 (14) | 0.0106 (15) |
C6D | 0.037 (2) | 0.0316 (19) | 0.0345 (19) | −0.0003 (15) | −0.0003 (15) | 0.0062 (15) |
C7D | 0.0370 (19) | 0.0321 (19) | 0.0261 (17) | 0.0011 (15) | −0.0034 (14) | 0.0022 (14) |
N1D | 0.054 (2) | 0.047 (2) | 0.037 (2) | 0.0023 (17) | 0.0142 (16) | 0.0094 (17) |
O1E | 0.0412 (15) | 0.0623 (18) | 0.0344 (14) | −0.0041 (13) | 0.0091 (12) | −0.0168 (13) |
O2E | 0.0359 (15) | 0.0607 (17) | 0.0374 (14) | −0.0031 (13) | −0.0043 (11) | −0.0180 (13) |
C1E | 0.033 (2) | 0.0341 (19) | 0.0281 (17) | 0.0008 (16) | −0.0010 (15) | −0.0002 (15) |
C2E | 0.0338 (19) | 0.0297 (18) | 0.0223 (16) | 0.0026 (15) | −0.0008 (14) | 0.0004 (13) |
C3E | 0.0291 (18) | 0.0358 (19) | 0.0262 (17) | 0.0000 (15) | −0.0020 (14) | 0.0012 (14) |
C4E | 0.0293 (18) | 0.0375 (19) | 0.0283 (17) | 0.0024 (15) | 0.0039 (14) | −0.0027 (15) |
C5E | 0.037 (2) | 0.0329 (19) | 0.0285 (17) | −0.0016 (16) | −0.0008 (15) | −0.0037 (15) |
C6E | 0.0273 (18) | 0.043 (2) | 0.0352 (19) | −0.0057 (16) | 0.0002 (15) | −0.0052 (16) |
C7E | 0.0293 (19) | 0.042 (2) | 0.0290 (17) | 0.0006 (16) | 0.0038 (14) | −0.0044 (15) |
N1E | 0.042 (2) | 0.065 (2) | 0.0324 (18) | −0.0076 (18) | 0.0046 (16) | −0.0193 (16) |
O1F | 0.0522 (18) | 0.079 (2) | 0.0379 (15) | −0.0014 (15) | 0.0062 (13) | −0.0198 (15) |
O2F | 0.0548 (17) | 0.0621 (18) | 0.0330 (14) | 0.0022 (14) | −0.0132 (13) | −0.0123 (13) |
C1F | 0.042 (2) | 0.0348 (19) | 0.0271 (17) | −0.0008 (16) | −0.0003 (17) | −0.0030 (15) |
C2F | 0.039 (2) | 0.0308 (18) | 0.0271 (17) | −0.0001 (15) | −0.0039 (15) | −0.0005 (14) |
C3F | 0.034 (2) | 0.036 (2) | 0.0358 (19) | 0.0029 (16) | −0.0058 (15) | −0.0050 (16) |
C4F | 0.0306 (19) | 0.040 (2) | 0.041 (2) | 0.0031 (16) | 0.0005 (16) | −0.0091 (16) |
C5F | 0.039 (2) | 0.0285 (18) | 0.0294 (18) | −0.0011 (15) | 0.0007 (15) | −0.0048 (14) |
C6F | 0.0340 (19) | 0.041 (2) | 0.0316 (18) | 0.0026 (16) | −0.0080 (15) | −0.0051 (16) |
C7F | 0.0293 (19) | 0.042 (2) | 0.0348 (19) | 0.0047 (16) | 0.0005 (15) | −0.0052 (16) |
N1F | 0.044 (2) | 0.061 (2) | 0.0398 (19) | 0.0006 (19) | −0.0009 (17) | −0.0208 (17) |
O1G | 0.0461 (16) | 0.0592 (18) | 0.0353 (14) | −0.0002 (13) | 0.0052 (12) | −0.0135 (13) |
O2G | 0.0466 (17) | 0.080 (2) | 0.0364 (14) | 0.0013 (15) | −0.0072 (13) | −0.0203 (14) |
C1G | 0.043 (2) | 0.0334 (19) | 0.0318 (18) | −0.0010 (17) | −0.0004 (17) | −0.0017 (15) |
C2G | 0.039 (2) | 0.0335 (19) | 0.0243 (17) | −0.0022 (16) | −0.0018 (15) | −0.0025 (14) |
C3G | 0.035 (2) | 0.044 (2) | 0.0320 (19) | −0.0098 (17) | 0.0065 (15) | −0.0057 (16) |
C4G | 0.034 (2) | 0.049 (2) | 0.0311 (18) | −0.0135 (17) | 0.0043 (15) | −0.0073 (16) |
C5G | 0.041 (2) | 0.0348 (19) | 0.0242 (17) | −0.0056 (16) | 0.0034 (15) | −0.0034 (14) |
C6G | 0.0315 (19) | 0.044 (2) | 0.0349 (19) | 0.0001 (16) | 0.0028 (15) | −0.0022 (16) |
C7G | 0.037 (2) | 0.044 (2) | 0.0325 (19) | 0.0007 (17) | −0.0066 (16) | −0.0057 (16) |
N1G | 0.037 (2) | 0.071 (2) | 0.0310 (17) | −0.0098 (19) | 0.0032 (16) | −0.0155 (16) |
O1H | 0.0408 (15) | 0.0398 (15) | 0.0484 (15) | 0.0002 (12) | 0.0058 (12) | 0.0000 (12) |
O2H | 0.0527 (17) | 0.0445 (16) | 0.0677 (19) | 0.0019 (13) | 0.0107 (14) | 0.0114 (14) |
O3H | 0.0409 (16) | 0.0590 (18) | 0.0587 (18) | −0.0032 (13) | −0.0049 (13) | 0.0117 (14) |
O4H | 0.0466 (18) | 0.129 (3) | 0.0521 (18) | 0.0261 (19) | 0.0174 (14) | 0.0319 (19) |
O5H | 0.0363 (14) | 0.0512 (16) | 0.0485 (16) | 0.0038 (12) | 0.0006 (12) | −0.0080 (13) |
O6H | 0.0450 (16) | 0.0382 (15) | 0.0556 (16) | 0.0059 (12) | −0.0016 (13) | −0.0025 (12) |
C1H | 0.060 (3) | 0.035 (2) | 0.069 (3) | −0.003 (2) | −0.008 (2) | 0.007 (2) |
C2H | 0.055 (3) | 0.045 (2) | 0.053 (2) | −0.011 (2) | 0.000 (2) | 0.010 (2) |
C3H | 0.038 (2) | 0.067 (3) | 0.043 (2) | 0.000 (2) | 0.0035 (18) | −0.007 (2) |
C4H | 0.034 (2) | 0.056 (3) | 0.067 (3) | 0.0008 (19) | −0.007 (2) | −0.018 (2) |
C5H | 0.046 (3) | 0.068 (3) | 0.136 (5) | 0.013 (2) | 0.020 (3) | 0.046 (3) |
C6H | 0.062 (3) | 0.082 (4) | 0.084 (4) | −0.009 (3) | −0.023 (3) | 0.038 (3) |
C7H | 0.082 (4) | 0.066 (3) | 0.045 (2) | 0.009 (3) | 0.003 (2) | 0.010 (2) |
C8H | 0.056 (3) | 0.126 (5) | 0.057 (3) | 0.008 (3) | 0.008 (2) | 0.040 (3) |
C9H | 0.039 (2) | 0.063 (3) | 0.059 (3) | −0.003 (2) | 0.016 (2) | −0.009 (2) |
C10H | 0.033 (2) | 0.057 (3) | 0.070 (3) | −0.002 (2) | 0.000 (2) | −0.007 (2) |
C11H | 0.041 (2) | 0.066 (3) | 0.067 (3) | 0.016 (2) | −0.005 (2) | 0.004 (2) |
C12H | 0.059 (3) | 0.048 (3) | 0.076 (3) | 0.018 (2) | 0.003 (2) | 0.002 (2) |
O1I | 0.071 (2) | 0.070 (2) | 0.0469 (17) | 0.0249 (17) | −0.0035 (15) | −0.0060 (15) |
O2I | 0.091 (3) | 0.0548 (19) | 0.0575 (19) | −0.0080 (18) | 0.0109 (17) | −0.0002 (15) |
O3I | 0.059 (2) | 0.074 (2) | 0.079 (2) | −0.0117 (17) | 0.0122 (17) | −0.0067 (18) |
O4I | 0.059 (2) | 0.072 (2) | 0.081 (2) | −0.0019 (17) | −0.0086 (18) | −0.0071 (19) |
O5I | 0.079 (2) | 0.063 (2) | 0.0562 (18) | 0.0079 (17) | −0.0019 (17) | 0.0018 (16) |
O6I | 0.0473 (18) | 0.080 (2) | 0.074 (2) | 0.0013 (16) | 0.0042 (16) | 0.0059 (18) |
C1I | 0.043 (3) | 0.085 (4) | 0.079 (3) | 0.001 (2) | 0.001 (2) | −0.013 (3) |
C2I | 0.037 (2) | 0.064 (3) | 0.078 (3) | −0.001 (2) | −0.012 (2) | −0.011 (3) |
C3I | 0.075 (3) | 0.081 (4) | 0.053 (3) | 0.025 (3) | −0.008 (2) | −0.004 (3) |
C4I | 0.072 (3) | 0.067 (3) | 0.061 (3) | 0.017 (3) | −0.004 (2) | 0.008 (2) |
C5I | 0.120 (5) | 0.057 (3) | 0.066 (3) | −0.018 (3) | 0.001 (3) | 0.007 (3) |
C6I | 0.082 (4) | 0.064 (3) | 0.093 (4) | −0.029 (3) | 0.011 (3) | 0.017 (3) |
C7I | 0.051 (3) | 0.123 (5) | 0.100 (4) | −0.022 (3) | 0.001 (3) | −0.009 (4) |
C8I | 0.035 (2) | 0.093 (4) | 0.084 (4) | 0.013 (2) | 0.005 (2) | −0.006 (3) |
C9I | 0.062 (3) | 0.077 (4) | 0.102 (4) | 0.010 (3) | −0.014 (3) | 0.018 (3) |
C10I | 0.079 (4) | 0.074 (3) | 0.065 (3) | 0.004 (3) | −0.027 (3) | 0.004 (3) |
C11I | 0.092 (4) | 0.055 (3) | 0.050 (3) | −0.006 (3) | 0.007 (3) | 0.005 (2) |
C12I | 0.075 (3) | 0.073 (3) | 0.055 (3) | −0.006 (3) | 0.022 (2) | 0.016 (2) |
Geometric parameters (Å, º) top
O1A—C2A | 1.410 (5) | O1F—H1F | 1.17 (7) |
O1A—C3A | 1.421 (5) | O2F—C1F | 1.268 (4) |
O2AA—C5A | 1.422 (8) | O2F—H1G | 1.35 (7) |
O2AA—C4AA | 1.472 (11) | C1F—C2F | 1.466 (5) |
O2AB—C5A | 1.329 (10) | C2F—C3F | 1.396 (5) |
O2AB—C4AB | 1.53 (2) | C2F—C7F | 1.397 (5) |
O3A—C6A | 1.419 (5) | C3F—C4F | 1.369 (5) |
O3A—C7A | 1.420 (5) | C3F—H3F | 0.9500 |
O4A—C8A | 1.418 (4) | C4F—C5F | 1.402 (5) |
O4A—C9A | 1.420 (5) | C4F—H4F | 0.9500 |
O5A—C10A | 1.423 (5) | C5F—N1F | 1.353 (5) |
O5A—C11A | 1.425 (4) | C5F—C6F | 1.402 (5) |
O6A—C1A | 1.419 (5) | C6F—C7F | 1.370 (5) |
O6A—C12A | 1.424 (5) | C6F—H6F | 0.9500 |
C1A—C2A | 1.482 (6) | C7F—H7F | 0.9500 |
C1A—H1AA | 0.9900 | N1F—H1FA | 0.87 (4) |
C1A—H1AB | 0.9900 | N1F—H1FB | 0.80 (6) |
C2A—H2AA | 0.9900 | O1G—C1G | 1.274 (4) |
C2A—H2AB | 0.9900 | O1G—H1G | 1.25 (7) |
C3A—C4AA | 1.470 (8) | O2G—C1G | 1.273 (4) |
C3A—C4AB | 1.773 (17) | O2G—H1F | 1.44 (7) |
C3A—H3AA | 0.9900 | C1G—C2G | 1.464 (5) |
C3A—H3AB | 0.9900 | C2G—C7G | 1.396 (5) |
C3A—H3AC | 0.9900 | C2G—C3G | 1.400 (5) |
C3A—H3AD | 0.9900 | C3G—C4G | 1.365 (5) |
C4AA—H4AA | 0.9900 | C3G—H3G | 0.9500 |
C4AA—H4AB | 0.9900 | C4G—C5G | 1.406 (5) |
C4AB—H4AC | 0.9900 | C4G—H4G | 0.9500 |
C4AB—H4AD | 0.9900 | C5G—N1G | 1.347 (4) |
C5A—C6A | 1.454 (7) | C5G—C6G | 1.405 (5) |
C5A—H5AA | 0.9900 | C6G—C7G | 1.375 (5) |
C5A—H5AB | 0.9900 | C6G—H6G | 0.9500 |
C5A—H5AC | 0.9900 | C7G—H7G | 0.9500 |
C5A—H5AD | 0.9900 | N1G—H1GA | 0.84 (4) |
C6A—H6AA | 0.9900 | N1G—H1GB | 0.82 (5) |
C6A—H6AB | 0.9900 | O1H—C3H | 1.414 (4) |
C7A—C8A | 1.494 (6) | O1H—C2H | 1.417 (5) |
C7A—H7AA | 0.9900 | O2H—C4H | 1.407 (5) |
C7A—H7AB | 0.9900 | O2H—C5H | 1.427 (5) |
C8A—H8AA | 0.9900 | O3H—C7H | 1.411 (5) |
C8A—H8AB | 0.9900 | O3H—C6H | 1.427 (5) |
C9A—C10A | 1.496 (6) | O4H—C9H | 1.383 (5) |
C9A—H9AA | 0.9900 | O4H—C8H | 1.429 (5) |
C9A—H9AB | 0.9900 | O5H—C10H | 1.417 (5) |
C10A—H10A | 0.9900 | O5H—C11H | 1.423 (5) |
C10A—H10B | 0.9900 | O6H—C12H | 1.418 (5) |
C11A—C12A | 1.492 (6) | O6H—C1H | 1.425 (5) |
C11A—H11A | 0.9900 | C1H—C2H | 1.499 (6) |
C11A—H11B | 0.9900 | C1H—H1HA | 0.9900 |
C12A—H12A | 0.9900 | C1H—H1HB | 0.9900 |
C12A—H12B | 0.9900 | C2H—H2HA | 0.9900 |
O1B—C1B | 1.281 (4) | C2H—H2HB | 0.9900 |
O1B—H1B | 1.04 (6) | C3H—C4H | 1.474 (6) |
O2B—C1B | 1.275 (4) | C3H—H3HA | 0.9900 |
C1B—C2B | 1.456 (5) | C3H—H3HB | 0.9900 |
C2B—C3B | 1.392 (5) | C4H—H4HA | 0.9900 |
C2B—C7B | 1.400 (5) | C4H—H4HB | 0.9900 |
C3B—C4B | 1.372 (5) | C5H—C6H | 1.455 (7) |
C3B—H3B | 0.9500 | C5H—H5HA | 0.9900 |
C4B—C5B | 1.406 (5) | C5H—H5HB | 0.9900 |
C4B—H4B | 0.9500 | C6H—H6HA | 0.9900 |
C5B—N1B | 1.346 (5) | C6H—H6HB | 0.9900 |
C5B—C6B | 1.407 (5) | C7H—C8H | 1.458 (7) |
C6B—C7B | 1.373 (5) | C7H—H7HA | 0.9900 |
C6B—H6B | 0.9500 | C7H—H7HB | 0.9900 |
C7B—H7B | 0.9500 | C8H—H8HA | 0.9900 |
N1B—H1BA | 0.85 (5) | C8H—H8HB | 0.9900 |
N1B—H1BB | 0.86 (6) | C9H—C10H | 1.488 (6) |
O1C—C1C | 1.308 (4) | C9H—H9HA | 0.9900 |
O1C—H1C | 1.01 (5) | C9H—H9HB | 0.9900 |
O2C—C1C | 1.241 (4) | C10H—H10C | 0.9900 |
C1C—C2C | 1.459 (4) | C10H—H10D | 0.9900 |
C2C—C7C | 1.385 (5) | C11H—C12H | 1.492 (6) |
C2C—C3C | 1.394 (5) | C11H—H11C | 0.9900 |
C3C—C4C | 1.369 (5) | C11H—H11D | 0.9900 |
C3C—H3C | 0.9500 | C12H—H12C | 0.9900 |
C4C—C5C | 1.400 (5) | C12H—H12D | 0.9900 |
C4C—H4C | 0.9500 | O1I—C3I | 1.393 (5) |
C5C—N1C | 1.353 (5) | O1I—C2I | 1.433 (5) |
C5C—C6C | 1.398 (5) | O2I—C5I | 1.374 (6) |
C6C—C7C | 1.374 (5) | O2I—C4I | 1.418 (6) |
C6C—H6C | 0.9500 | O3I—C7I | 1.375 (6) |
C7C—H7C | 0.9500 | O3I—C6I | 1.415 (6) |
N1C—H1CA | 0.83 (5) | O4I—C9I | 1.392 (6) |
N1C—H1CB | 0.81 (5) | O4I—C8I | 1.400 (6) |
O1D—C1D | 1.317 (4) | O5I—C11I | 1.367 (5) |
O1D—H1D | 0.8400 | O5I—C10I | 1.469 (6) |
O2D—C1D | 1.236 (4) | O6I—C1I | 1.387 (5) |
C1D—C2D | 1.454 (4) | O6I—C12I | 1.432 (5) |
C2D—C3D | 1.396 (5) | C1I—C2I | 1.465 (7) |
C2D—C7D | 1.403 (5) | C1I—H1IA | 0.9900 |
C3D—C4D | 1.373 (5) | C1I—H1IB | 0.9900 |
C3D—H3D | 0.9500 | C2I—H2IA | 0.9900 |
C4D—C5D | 1.409 (5) | C2I—H2IB | 0.9900 |
C4D—H4D | 0.9500 | C3I—C4I | 1.468 (7) |
C5D—N1D | 1.343 (4) | C3I—H3IA | 0.9900 |
C5D—C6D | 1.402 (5) | C3I—H3IB | 0.9900 |
C6D—C7D | 1.367 (5) | C4I—H4IA | 0.9900 |
C6D—H6D | 0.9500 | C4I—H4IB | 0.9900 |
C7D—H7D | 0.9500 | C5I—C6I | 1.514 (8) |
N1D—H1DA | 0.85 (5) | C5I—H5IA | 0.9900 |
N1D—H1DB | 0.86 (5) | C5I—H5IB | 0.9900 |
O1E—C1E | 1.285 (4) | C6I—H6IA | 0.9900 |
O1E—H1E | 1.12 (6) | C6I—H6IB | 0.9900 |
O2E—C1E | 1.267 (4) | C7I—C8I | 1.539 (8) |
C1E—C2E | 1.463 (4) | C7I—H7IA | 0.9900 |
C2E—C3E | 1.397 (4) | C7I—H7IB | 0.9900 |
C2E—C7E | 1.399 (5) | C8I—H8IA | 0.9900 |
C3E—C4E | 1.367 (4) | C8I—H8IB | 0.9900 |
C3E—H3E | 0.9500 | C9I—C10I | 1.488 (7) |
C4E—C5E | 1.411 (5) | C9I—H9IA | 0.9900 |
C4E—H4E | 0.9500 | C9I—H9IB | 0.9900 |
C5E—N1E | 1.350 (4) | C10I—H10E | 0.9900 |
C5E—C6E | 1.407 (5) | C10I—H10F | 0.9900 |
C6E—C7E | 1.366 (5) | C11I—C12I | 1.490 (7) |
C6E—H6E | 0.9500 | C11I—H11E | 0.9900 |
C7E—H7E | 0.9500 | C11I—H11F | 0.9900 |
N1E—H1EA | 0.89 (4) | C12I—H12E | 0.9900 |
N1E—H1EB | 0.82 (4) | C12I—H12F | 0.9900 |
O1F—C1F | 1.281 (4) | | |
| | | |
C2A—O1A—C3A | 112.4 (3) | C3F—C2F—C1F | 120.0 (3) |
C5A—O2AA—C4AA | 112.7 (6) | C7F—C2F—C1F | 121.6 (3) |
C5A—O2AB—C4AB | 102.0 (10) | C4F—C3F—C2F | 120.8 (3) |
C6A—O3A—C7A | 114.0 (3) | C4F—C3F—H3F | 119.6 |
C8A—O4A—C9A | 113.8 (3) | C2F—C3F—H3F | 119.6 |
C10A—O5A—C11A | 112.7 (3) | C3F—C4F—C5F | 120.9 (3) |
C1A—O6A—C12A | 112.0 (3) | C3F—C4F—H4F | 119.5 |
O6A—C1A—C2A | 109.3 (3) | C5F—C4F—H4F | 119.5 |
O6A—C1A—H1AA | 109.8 | N1F—C5F—C4F | 120.7 (3) |
C2A—C1A—H1AA | 109.8 | N1F—C5F—C6F | 121.1 (3) |
O6A—C1A—H1AB | 109.8 | C4F—C5F—C6F | 118.2 (3) |
C2A—C1A—H1AB | 109.8 | C7F—C6F—C5F | 120.6 (3) |
H1AA—C1A—H1AB | 108.3 | C7F—C6F—H6F | 119.7 |
O1A—C2A—C1A | 107.7 (3) | C5F—C6F—H6F | 119.7 |
O1A—C2A—H2AA | 110.2 | C6F—C7F—C2F | 121.1 (3) |
C1A—C2A—H2AA | 110.2 | C6F—C7F—H7F | 119.5 |
O1A—C2A—H2AB | 110.2 | C2F—C7F—H7F | 119.5 |
C1A—C2A—H2AB | 110.2 | C5F—N1F—H1FA | 116 (3) |
H2AA—C2A—H2AB | 108.5 | C5F—N1F—H1FB | 114 (4) |
O1A—C3A—C4AA | 106.9 (4) | H1FA—N1F—H1FB | 126 (5) |
O1A—C3A—C4AB | 112.2 (6) | C1G—O1G—H1G | 116 (3) |
O1A—C3A—H3AA | 110.4 | C1G—O2G—H1F | 118 (3) |
C4AA—C3A—H3AA | 110.4 | O2G—C1G—O1G | 122.4 (3) |
O1A—C3A—H3AB | 110.4 | O2G—C1G—C2G | 118.7 (3) |
C4AA—C3A—H3AB | 110.4 | O1G—C1G—C2G | 118.8 (3) |
H3AA—C3A—H3AB | 108.6 | C7G—C2G—C3G | 118.2 (3) |
O1A—C3A—H3AC | 109.2 | C7G—C2G—C1G | 120.2 (3) |
C4AB—C3A—H3AC | 109.2 | C3G—C2G—C1G | 121.6 (3) |
O1A—C3A—H3AD | 109.2 | C4G—C3G—C2G | 120.8 (3) |
C4AB—C3A—H3AD | 109.2 | C4G—C3G—H3G | 119.6 |
H3AC—C3A—H3AD | 107.9 | C2G—C3G—H3G | 119.6 |
C3A—C4AA—O2AA | 104.6 (6) | C3G—C4G—C5G | 121.2 (3) |
C3A—C4AA—H4AA | 110.8 | C3G—C4G—H4G | 119.4 |
O2AA—C4AA—H4AA | 110.8 | C5G—C4G—H4G | 119.4 |
C3A—C4AA—H4AB | 110.8 | N1G—C5G—C6G | 120.9 (3) |
O2AA—C4AA—H4AB | 110.8 | N1G—C5G—C4G | 120.9 (3) |
H4AA—C4AA—H4AB | 108.9 | C6G—C5G—C4G | 118.1 (3) |
O2AB—C4AB—C3A | 95.2 (9) | C7G—C6G—C5G | 120.2 (3) |
O2AB—C4AB—H4AC | 112.7 | C7G—C6G—H6G | 119.9 |
C3A—C4AB—H4AC | 112.7 | C5G—C6G—H6G | 119.9 |
O2AB—C4AB—H4AD | 112.7 | C6G—C7G—C2G | 121.5 (3) |
C3A—C4AB—H4AD | 112.7 | C6G—C7G—H7G | 119.3 |
H4AC—C4AB—H4AD | 110.2 | C2G—C7G—H7G | 119.3 |
O2AB—C5A—C6A | 132.0 (7) | C5G—N1G—H1GA | 120 (3) |
O2AA—C5A—C6A | 105.7 (6) | C5G—N1G—H1GB | 119 (3) |
O2AA—C5A—H5AA | 110.6 | H1GA—N1G—H1GB | 119 (4) |
C6A—C5A—H5AA | 110.6 | C3H—O1H—C2H | 112.7 (3) |
O2AA—C5A—H5AB | 110.6 | C4H—O2H—C5H | 112.8 (4) |
C6A—C5A—H5AB | 110.6 | C7H—O3H—C6H | 112.2 (4) |
H5AA—C5A—H5AB | 108.7 | C9H—O4H—C8H | 114.0 (3) |
O2AB—C5A—H5AC | 104.2 | C10H—O5H—C11H | 112.1 (3) |
C6A—C5A—H5AC | 104.2 | C12H—O6H—C1H | 112.5 (3) |
O2AB—C5A—H5AD | 104.2 | O6H—C1H—C2H | 109.5 (3) |
C6A—C5A—H5AD | 104.2 | O6H—C1H—H1HA | 109.8 |
H5AC—C5A—H5AD | 105.6 | C2H—C1H—H1HA | 109.8 |
O3A—C6A—C5A | 116.0 (4) | O6H—C1H—H1HB | 109.8 |
O3A—C6A—H6AA | 108.3 | C2H—C1H—H1HB | 109.8 |
C5A—C6A—H6AA | 108.3 | H1HA—C1H—H1HB | 108.2 |
O3A—C6A—H6AB | 108.3 | O1H—C2H—C1H | 108.0 (3) |
C5A—C6A—H6AB | 108.3 | O1H—C2H—H2HA | 110.1 |
H6AA—C6A—H6AB | 107.4 | C1H—C2H—H2HA | 110.1 |
O3A—C7A—C8A | 109.3 (3) | O1H—C2H—H2HB | 110.1 |
O3A—C7A—H7AA | 109.8 | C1H—C2H—H2HB | 110.1 |
C8A—C7A—H7AA | 109.8 | H2HA—C2H—H2HB | 108.4 |
O3A—C7A—H7AB | 109.8 | O1H—C3H—C4H | 109.5 (3) |
C8A—C7A—H7AB | 109.8 | O1H—C3H—H3HA | 109.8 |
H7AA—C7A—H7AB | 108.3 | C4H—C3H—H3HA | 109.8 |
O4A—C8A—C7A | 108.6 (3) | O1H—C3H—H3HB | 109.8 |
O4A—C8A—H8AA | 110.0 | C4H—C3H—H3HB | 109.8 |
C7A—C8A—H8AA | 110.0 | H3HA—C3H—H3HB | 108.2 |
O4A—C8A—H8AB | 110.0 | O2H—C4H—C3H | 109.8 (3) |
C7A—C8A—H8AB | 110.0 | O2H—C4H—H4HA | 109.7 |
H8AA—C8A—H8AB | 108.3 | C3H—C4H—H4HA | 109.7 |
O4A—C9A—C10A | 108.4 (3) | O2H—C4H—H4HB | 109.7 |
O4A—C9A—H9AA | 110.0 | C3H—C4H—H4HB | 109.7 |
C10A—C9A—H9AA | 110.0 | H4HA—C4H—H4HB | 108.2 |
O4A—C9A—H9AB | 110.0 | O2H—C5H—C6H | 110.6 (4) |
C10A—C9A—H9AB | 110.0 | O2H—C5H—H5HA | 109.5 |
H9AA—C9A—H9AB | 108.4 | C6H—C5H—H5HA | 109.5 |
O5A—C10A—C9A | 109.1 (3) | O2H—C5H—H5HB | 109.5 |
O5A—C10A—H10A | 109.9 | C6H—C5H—H5HB | 109.5 |
C9A—C10A—H10A | 109.9 | H5HA—C5H—H5HB | 108.1 |
O5A—C10A—H10B | 109.9 | O3H—C6H—C5H | 110.6 (4) |
C9A—C10A—H10B | 109.9 | O3H—C6H—H6HA | 109.5 |
H10A—C10A—H10B | 108.3 | C5H—C6H—H6HA | 109.5 |
O5A—C11A—C12A | 109.3 (3) | O3H—C6H—H6HB | 109.5 |
O5A—C11A—H11A | 109.8 | C5H—C6H—H6HB | 109.5 |
C12A—C11A—H11A | 109.8 | H6HA—C6H—H6HB | 108.1 |
O5A—C11A—H11B | 109.8 | O3H—C7H—C8H | 109.4 (4) |
C12A—C11A—H11B | 109.8 | O3H—C7H—H7HA | 109.8 |
H11A—C11A—H11B | 108.3 | C8H—C7H—H7HA | 109.8 |
O6A—C12A—C11A | 108.6 (3) | O3H—C7H—H7HB | 109.8 |
O6A—C12A—H12A | 110.0 | C8H—C7H—H7HB | 109.8 |
C11A—C12A—H12A | 110.0 | H7HA—C7H—H7HB | 108.2 |
O6A—C12A—H12B | 110.0 | O4H—C8H—C7H | 109.5 (4) |
C11A—C12A—H12B | 110.0 | O4H—C8H—H8HA | 109.8 |
H12A—C12A—H12B | 108.3 | C7H—C8H—H8HA | 109.8 |
C1B—O1B—H1B | 120 (3) | O4H—C8H—H8HB | 109.8 |
O2B—C1B—O1B | 121.6 (3) | C7H—C8H—H8HB | 109.8 |
O2B—C1B—C2B | 119.7 (3) | H8HA—C8H—H8HB | 108.2 |
O1B—C1B—C2B | 118.7 (3) | O4H—C9H—C10H | 109.7 (3) |
C3B—C2B—C7B | 117.9 (3) | O4H—C9H—H9HA | 109.7 |
C3B—C2B—C1B | 121.5 (3) | C10H—C9H—H9HA | 109.7 |
C7B—C2B—C1B | 120.6 (3) | O4H—C9H—H9HB | 109.7 |
C4B—C3B—C2B | 122.4 (3) | C10H—C9H—H9HB | 109.7 |
C4B—C3B—H3B | 118.8 | H9HA—C9H—H9HB | 108.2 |
C2B—C3B—H3B | 118.8 | O5H—C10H—C9H | 109.7 (3) |
C3B—C4B—C5B | 119.7 (3) | O5H—C10H—H10C | 109.7 |
C3B—C4B—H4B | 120.1 | C9H—C10H—H10C | 109.7 |
C5B—C4B—H4B | 120.1 | O5H—C10H—H10D | 109.7 |
N1B—C5B—C4B | 121.4 (4) | C9H—C10H—H10D | 109.7 |
N1B—C5B—C6B | 120.4 (4) | H10C—C10H—H10D | 108.2 |
C4B—C5B—C6B | 118.3 (3) | O5H—C11H—C12H | 109.3 (4) |
C7B—C6B—C5B | 121.1 (3) | O5H—C11H—H11C | 109.8 |
C7B—C6B—H6B | 119.5 | C12H—C11H—H11C | 109.8 |
C5B—C6B—H6B | 119.5 | O5H—C11H—H11D | 109.8 |
C6B—C7B—C2B | 120.7 (3) | C12H—C11H—H11D | 109.8 |
C6B—C7B—H7B | 119.7 | H11C—C11H—H11D | 108.3 |
C2B—C7B—H7B | 119.7 | O6H—C12H—C11H | 109.3 (3) |
C5B—N1B—H1BA | 120 (3) | O6H—C12H—H12C | 109.8 |
C5B—N1B—H1BB | 117 (3) | C11H—C12H—H12C | 109.8 |
H1BA—N1B—H1BB | 120 (5) | O6H—C12H—H12D | 109.8 |
C1C—O1C—H1C | 112 (3) | C11H—C12H—H12D | 109.8 |
O2C—C1C—O1C | 121.9 (3) | H12C—C12H—H12D | 108.3 |
O2C—C1C—C2C | 121.9 (3) | C3I—O1I—C2I | 112.5 (4) |
O1C—C1C—C2C | 116.1 (3) | C5I—O2I—C4I | 114.5 (4) |
C7C—C2C—C3C | 118.0 (3) | C7I—O3I—C6I | 113.6 (4) |
C7C—C2C—C1C | 121.8 (3) | C9I—O4I—C8I | 111.3 (4) |
C3C—C2C—C1C | 120.1 (3) | C11I—O5I—C10I | 111.4 (4) |
C4C—C3C—C2C | 121.1 (3) | C1I—O6I—C12I | 113.8 (4) |
C4C—C3C—H3C | 119.5 | O6I—C1I—C2I | 109.0 (4) |
C2C—C3C—H3C | 119.5 | O6I—C1I—H1IA | 109.9 |
C3C—C4C—C5C | 121.2 (3) | C2I—C1I—H1IA | 109.9 |
C3C—C4C—H4C | 119.4 | O6I—C1I—H1IB | 109.9 |
C5C—C4C—H4C | 119.4 | C2I—C1I—H1IB | 109.9 |
N1C—C5C—C6C | 121.5 (4) | H1IA—C1I—H1IB | 108.3 |
N1C—C5C—C4C | 121.2 (4) | O1I—C2I—C1I | 111.2 (4) |
C6C—C5C—C4C | 117.3 (3) | O1I—C2I—H2IA | 109.4 |
C7C—C6C—C5C | 121.1 (3) | C1I—C2I—H2IA | 109.4 |
C7C—C6C—H6C | 119.4 | O1I—C2I—H2IB | 109.4 |
C5C—C6C—H6C | 119.4 | C1I—C2I—H2IB | 109.4 |
C6C—C7C—C2C | 121.2 (3) | H2IA—C2I—H2IB | 108.0 |
C6C—C7C—H7C | 119.4 | O1I—C3I—C4I | 109.0 (4) |
C2C—C7C—H7C | 119.4 | O1I—C3I—H3IA | 109.9 |
C5C—N1C—H1CA | 115 (3) | C4I—C3I—H3IA | 109.9 |
C5C—N1C—H1CB | 119 (4) | O1I—C3I—H3IB | 109.9 |
H1CA—N1C—H1CB | 124 (5) | C4I—C3I—H3IB | 109.9 |
C1D—O1D—H1D | 109.5 | H3IA—C3I—H3IB | 108.3 |
O2D—C1D—O1D | 122.0 (3) | O2I—C4I—C3I | 111.3 (4) |
O2D—C1D—C2D | 121.8 (3) | O2I—C4I—H4IA | 109.4 |
O1D—C1D—C2D | 116.3 (3) | C3I—C4I—H4IA | 109.4 |
C3D—C2D—C7D | 118.1 (3) | O2I—C4I—H4IB | 109.4 |
C3D—C2D—C1D | 122.8 (3) | C3I—C4I—H4IB | 109.4 |
C7D—C2D—C1D | 119.1 (3) | H4IA—C4I—H4IB | 108.0 |
C4D—C3D—C2D | 121.3 (3) | O2I—C5I—C6I | 109.4 (4) |
C4D—C3D—H3D | 119.3 | O2I—C5I—H5IA | 109.8 |
C2D—C3D—H3D | 119.3 | C6I—C5I—H5IA | 109.8 |
C3D—C4D—C5D | 120.6 (3) | O2I—C5I—H5IB | 109.8 |
C3D—C4D—H4D | 119.7 | C6I—C5I—H5IB | 109.8 |
C5D—C4D—H4D | 119.7 | H5IA—C5I—H5IB | 108.2 |
N1D—C5D—C6D | 120.4 (4) | O3I—C6I—C5I | 109.1 (4) |
N1D—C5D—C4D | 122.0 (3) | O3I—C6I—H6IA | 109.9 |
C6D—C5D—C4D | 117.7 (3) | C5I—C6I—H6IA | 109.9 |
C7D—C6D—C5D | 121.5 (3) | O3I—C6I—H6IB | 109.9 |
C7D—C6D—H6D | 119.3 | C5I—C6I—H6IB | 109.9 |
C5D—C6D—H6D | 119.3 | H6IA—C6I—H6IB | 108.3 |
C6D—C7D—C2D | 120.8 (3) | O3I—C7I—C8I | 109.2 (4) |
C6D—C7D—H7D | 119.6 | O3I—C7I—H7IA | 109.8 |
C2D—C7D—H7D | 119.6 | C8I—C7I—H7IA | 109.8 |
C5D—N1D—H1DA | 122 (4) | O3I—C7I—H7IB | 109.8 |
C5D—N1D—H1DB | 119 (3) | C8I—C7I—H7IB | 109.8 |
H1DA—N1D—H1DB | 116 (5) | H7IA—C7I—H7IB | 108.3 |
C1E—O1E—H1E | 114 (3) | O4I—C8I—C7I | 109.5 (4) |
O2E—C1E—O1E | 122.1 (3) | O4I—C8I—H8IA | 109.8 |
O2E—C1E—C2E | 120.4 (3) | C7I—C8I—H8IA | 109.8 |
O1E—C1E—C2E | 117.6 (3) | O4I—C8I—H8IB | 109.8 |
C3E—C2E—C7E | 118.1 (3) | C7I—C8I—H8IB | 109.8 |
C3E—C2E—C1E | 121.9 (3) | H8IA—C8I—H8IB | 108.2 |
C7E—C2E—C1E | 120.0 (3) | O4I—C9I—C10I | 111.3 (5) |
C4E—C3E—C2E | 121.3 (3) | O4I—C9I—H9IA | 109.4 |
C4E—C3E—H3E | 119.3 | C10I—C9I—H9IA | 109.4 |
C2E—C3E—H3E | 119.3 | O4I—C9I—H9IB | 109.4 |
C3E—C4E—C5E | 120.6 (3) | C10I—C9I—H9IB | 109.4 |
C3E—C4E—H4E | 119.7 | H9IA—C9I—H9IB | 108.0 |
C5E—C4E—H4E | 119.7 | O5I—C10I—C9I | 107.7 (4) |
N1E—C5E—C6E | 121.4 (3) | O5I—C10I—H10E | 110.2 |
N1E—C5E—C4E | 120.7 (3) | C9I—C10I—H10E | 110.2 |
C6E—C5E—C4E | 117.9 (3) | O5I—C10I—H10F | 110.2 |
C7E—C6E—C5E | 120.8 (3) | C9I—C10I—H10F | 110.2 |
C7E—C6E—H6E | 119.6 | H10E—C10I—H10F | 108.5 |
C5E—C6E—H6E | 119.6 | O5I—C11I—C12I | 108.3 (4) |
C6E—C7E—C2E | 121.2 (3) | O5I—C11I—H11E | 110.0 |
C6E—C7E—H7E | 119.4 | C12I—C11I—H11E | 110.0 |
C2E—C7E—H7E | 119.4 | O5I—C11I—H11F | 110.0 |
C5E—N1E—H1EA | 124 (2) | C12I—C11I—H11F | 110.0 |
C5E—N1E—H1EB | 111 (3) | H11E—C11I—H11F | 108.4 |
H1EA—N1E—H1EB | 125 (4) | O6I—C12I—C11I | 110.0 (4) |
C1F—O1F—H1F | 113 (3) | O6I—C12I—H12E | 109.7 |
C1F—O2F—H1G | 120 (3) | C11I—C12I—H12E | 109.7 |
O2F—C1F—O1F | 122.4 (3) | O6I—C12I—H12F | 109.7 |
O2F—C1F—C2F | 119.0 (3) | C11I—C12I—H12F | 109.7 |
O1F—C1F—C2F | 118.6 (3) | H12E—C12I—H12F | 108.2 |
C3F—C2F—C7F | 118.4 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12A—H12A···O2Bi | 0.99 | 2.65 | 3.550 (5) | 151 |
O1B—H1B···O2Bii | 1.04 (6) | 1.57 (6) | 2.604 (4) | 175 (5) |
N1B—H1BA···O6I | 0.85 (5) | 2.37 (5) | 3.138 (5) | 150 (4) |
N1B—H1BB···O2I | 0.86 (6) | 2.60 (5) | 3.280 (5) | 138 (4) |
N1B—H1BB···O3I | 0.86 (6) | 2.27 (6) | 3.061 (5) | 154 (5) |
O1C—H1C···O2D | 1.01 (5) | 1.60 (6) | 2.600 (3) | 170 (5) |
N1C—H1CA···O4Aiii | 0.83 (5) | 2.58 (5) | 3.153 (5) | 127 (4) |
N1C—H1CA···O5Aiii | 0.83 (5) | 2.25 (5) | 3.055 (5) | 164 (4) |
N1C—H1CB···O1Aiii | 0.81 (5) | 2.25 (5) | 2.998 (5) | 153 (5) |
O1D—H1D···O2C | 0.84 | 1.78 | 2.617 (3) | 172 |
N1D—H1DA···O4Hiv | 0.85 (5) | 2.23 (5) | 2.961 (4) | 144 (5) |
N1D—H1DB···O5Hiv | 0.86 (5) | 2.64 (5) | 3.102 (4) | 114 (4) |
N1D—H1DB···O6Hiv | 0.86 (5) | 2.30 (5) | 3.148 (5) | 165 (4) |
O1E—H1E···O2Ev | 1.12 (6) | 1.50 (7) | 2.622 (3) | 172 (5) |
N1E—H1EA···O1H | 0.89 (4) | 2.30 (4) | 3.069 (4) | 144 (3) |
N1E—H1EA···O2H | 0.89 (4) | 2.63 (4) | 3.403 (5) | 147 (3) |
N1E—H1EB···O5H | 0.82 (4) | 2.33 (5) | 3.125 (5) | 162 (4) |
O1F—H1F···O1G | 1.17 (7) | 2.64 (7) | 3.483 (4) | 128 (4) |
O1F—H1F···O2G | 1.17 (7) | 1.44 (7) | 2.600 (3) | 171 (6) |
O2G—H1F···O2F | 1.44 (7) | 2.42 (7) | 3.370 (4) | 119 (4) |
N1F—H1FA···O3I | 0.87 (4) | 2.33 (4) | 3.083 (5) | 145 (4) |
N1F—H1FA···O4I | 0.87 (4) | 2.63 (4) | 3.380 (5) | 145 (3) |
N1F—H1FB···O1I | 0.80 (6) | 2.41 (6) | 3.165 (5) | 159 (5) |
N1F—H1FB···O6I | 0.80 (6) | 2.65 (6) | 3.215 (5) | 129 (5) |
O2F—H1G···O2G | 1.35 (7) | 2.50 (7) | 3.370 (4) | 119 (4) |
O1G—H1G···O1F | 1.25 (7) | 2.62 (7) | 3.483 (4) | 124 (4) |
O1G—H1G···O2F | 1.25 (7) | 1.35 (7) | 2.604 (3) | 177 (6) |
N1G—H1GA···O6Avi | 0.84 (4) | 2.24 (4) | 3.058 (5) | 168 (3) |
N1G—H1GB···O3Avi | 0.82 (5) | 2.59 (5) | 3.353 (5) | 156 (4) |
N1G—H1GB···O4Avi | 0.82 (5) | 2.41 (5) | 3.058 (4) | 136 (4) |
C3H—H3HB···O2Cvii | 0.99 | 2.63 | 3.504 (5) | 148 |
C7I—H7IA···O2D | 0.99 | 2.53 | 3.494 (6) | 164 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+1, −z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1, y, z. |
(2) 18-crown-6/4-aminobenzoic acid/bis(3,5-dinitrobenzoic acid)
top
Crystal data top
C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2 | Z = 2 |
Mr = 825.69 | F(000) = 864 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
a = 7.6055 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.0157 (4) Å | Cell parameters from 9094 reflections |
c = 16.4476 (4) Å | θ = 2.6–24.5° |
α = 73.156 (2)° | µ = 0.12 mm−1 |
β = 85.540 (2)° | T = 173 K |
γ = 89.562 (1)° | Block, colourless |
V = 1911.45 (9) Å3 | 0.24 × 0.21 × 0.17 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 6336 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.047 |
Absorption correction: multi-scan SADABS (Bruker, 2008) | θmax = 30.0°, θmin = 2.1° |
Tmin = 0.971, Tmax = 0.980 | h = −10→9 |
50498 measured reflections | k = −22→22 |
10356 independent reflections | l = −23→23 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.335P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
10356 reflections | Δρmax = 0.29 e Å−3 |
543 parameters | Δρmin = −0.27 e Å−3 |
Crystal data top
C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2 | γ = 89.562 (1)° |
Mr = 825.69 | V = 1911.45 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.6055 (2) Å | Mo Kα radiation |
b = 16.0157 (4) Å | µ = 0.12 mm−1 |
c = 16.4476 (4) Å | T = 173 K |
α = 73.156 (2)° | 0.24 × 0.21 × 0.17 mm |
β = 85.540 (2)° | |
Data collection top
Bruker APEX-II CCD diffractometer | 10356 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2008) | 6336 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.980 | Rint = 0.047 |
50498 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.29 e Å−3 |
10356 reflections | Δρmin = −0.27 e Å−3 |
543 parameters | |
Special details top
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. H atoms of carboxyl and ammonium groups refined freely |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.70311 (14) | 0.39418 (6) | 0.26256 (7) | 0.0279 (3) | |
O2 | 0.40686 (14) | 0.40691 (7) | 0.37024 (7) | 0.0299 (3) | |
O3 | 0.33487 (14) | 0.57182 (7) | 0.39547 (7) | 0.0299 (3) | |
O4 | 0.62524 (14) | 0.68320 (7) | 0.37789 (7) | 0.0318 (3) | |
O5 | 0.88839 (13) | 0.67812 (7) | 0.25440 (7) | 0.0295 (3) | |
O6 | 0.96446 (14) | 0.52168 (7) | 0.21671 (7) | 0.0305 (3) | |
C1 | 0.6015 (2) | 0.31942 (10) | 0.31118 (10) | 0.0309 (4) | |
H1A | 0.6477 | 0.2955 | 0.3678 | 0.037* | |
H1B | 0.6085 | 0.2736 | 0.2816 | 0.037* | |
C2 | 0.4151 (2) | 0.34646 (10) | 0.32111 (11) | 0.0327 (4) | |
H2A | 0.3718 | 0.3741 | 0.2644 | 0.039* | |
H2B | 0.3395 | 0.2947 | 0.3502 | 0.039* | |
C3 | 0.2330 (2) | 0.43650 (12) | 0.38119 (14) | 0.0445 (5) | |
H3A | 0.1524 | 0.3861 | 0.4076 | 0.053* | |
H3B | 0.1916 | 0.4684 | 0.3251 | 0.053* | |
C4 | 0.2322 (2) | 0.49527 (12) | 0.43688 (13) | 0.0459 (5) | |
H4A | 0.1095 | 0.5116 | 0.4496 | 0.055* | |
H4B | 0.2812 | 0.4644 | 0.4914 | 0.055* | |
C5 | 0.3488 (2) | 0.62711 (12) | 0.44900 (11) | 0.0374 (4) | |
H5A | 0.4083 | 0.5959 | 0.5004 | 0.045* | |
H5B | 0.2296 | 0.6432 | 0.4676 | 0.045* | |
C6 | 0.4522 (2) | 0.70760 (12) | 0.40082 (12) | 0.0372 (4) | |
H6A | 0.3938 | 0.7384 | 0.3489 | 0.045* | |
H6B | 0.4584 | 0.7475 | 0.4366 | 0.045* | |
C7 | 0.7363 (2) | 0.75782 (11) | 0.33862 (12) | 0.0342 (4) | |
H7A | 0.7504 | 0.7918 | 0.3794 | 0.041* | |
H7B | 0.6823 | 0.7959 | 0.2884 | 0.041* | |
C8 | 0.9121 (2) | 0.72813 (11) | 0.31175 (11) | 0.0328 (4) | |
H8A | 0.9897 | 0.7793 | 0.2834 | 0.039* | |
H8B | 0.9684 | 0.6922 | 0.3623 | 0.039* | |
C9 | 1.0512 (2) | 0.66551 (11) | 0.21064 (12) | 0.0354 (4) | |
H9A | 1.1393 | 0.6414 | 0.2522 | 0.042* | |
H9B | 1.0972 | 0.7221 | 0.1723 | 0.042* | |
C10 | 1.0214 (2) | 0.60366 (11) | 0.15975 (12) | 0.0356 (4) | |
H10A | 0.9307 | 0.6269 | 0.1193 | 0.043* | |
H10B | 1.1321 | 0.5967 | 0.1266 | 0.043* | |
C11 | 0.9625 (2) | 0.45348 (11) | 0.17689 (11) | 0.0334 (4) | |
H11A | 1.0844 | 0.4409 | 0.1585 | 0.040* | |
H11B | 0.8941 | 0.4715 | 0.1260 | 0.040* | |
C12 | 0.8797 (2) | 0.37377 (10) | 0.23964 (11) | 0.0315 (4) | |
H12A | 0.8795 | 0.3250 | 0.2139 | 0.038* | |
H12B | 0.9473 | 0.3560 | 0.2908 | 0.038* | |
O1A | 0.3640 (2) | 0.68524 (10) | −0.11356 (8) | 0.0602 (4) | |
O2A | 0.28934 (18) | 0.80021 (8) | −0.06845 (8) | 0.0394 (3) | |
H2 | 0.247 (3) | 0.8174 (15) | −0.1184 (15) | 0.067 (7)* | |
N1A | 0.60982 (18) | 0.56401 (9) | 0.26723 (8) | 0.0204 (3) | |
H1AA | 0.642 (2) | 0.5062 (13) | 0.2708 (11) | 0.041 (5)* | |
H1AB | 0.524 (3) | 0.5626 (13) | 0.3143 (14) | 0.065 (7)* | |
H1AC | 0.706 (3) | 0.5971 (13) | 0.2738 (13) | 0.057 (6)* | |
C1A | 0.42739 (19) | 0.68403 (10) | 0.02546 (9) | 0.0232 (3) | |
C2A | 0.4710 (2) | 0.59662 (10) | 0.04806 (10) | 0.0294 (4) | |
H2AA | 0.4612 | 0.5642 | 0.0085 | 0.035* | |
C3A | 0.5286 (2) | 0.55583 (10) | 0.12741 (10) | 0.0264 (3) | |
H3AA | 0.5559 | 0.4956 | 0.1431 | 0.032* | |
C4A | 0.54573 (18) | 0.60465 (9) | 0.18336 (9) | 0.0189 (3) | |
C5A | 0.50679 (19) | 0.69238 (9) | 0.16142 (9) | 0.0229 (3) | |
H5AA | 0.5218 | 0.7253 | 0.2001 | 0.027* | |
C6A | 0.4456 (2) | 0.73183 (10) | 0.08238 (10) | 0.0239 (3) | |
H6AA | 0.4160 | 0.7918 | 0.0672 | 0.029* | |
C7A | 0.3578 (2) | 0.72278 (11) | −0.05982 (10) | 0.0292 (4) | |
O1B | −0.0111 (2) | 0.76497 (10) | 0.54022 (10) | 0.0747 (5) | |
O2B | 0.09603 (19) | 0.83518 (9) | 0.41577 (9) | 0.0542 (4) | |
O3B | 0.3662 (2) | 1.11868 (8) | 0.36788 (7) | 0.0485 (4) | |
O4B | 0.44509 (17) | 1.15604 (7) | 0.47528 (8) | 0.0428 (3) | |
O5B | 0.1948 (2) | 0.99992 (9) | 0.76123 (8) | 0.0619 (4) | |
O6B | 0.15325 (16) | 0.85646 (8) | 0.78650 (7) | 0.0366 (3) | |
N1B | 0.06927 (18) | 0.82635 (9) | 0.49122 (10) | 0.0335 (3) | |
N2B | 0.37000 (18) | 1.10703 (8) | 0.44430 (8) | 0.0281 (3) | |
C1B | 0.1869 (2) | 0.94501 (10) | 0.64432 (9) | 0.0242 (3) | |
C2B | 0.12106 (19) | 0.88119 (10) | 0.61256 (10) | 0.0242 (3) | |
H2BA | 0.0661 | 0.8297 | 0.6499 | 0.029* | |
C3B | 0.13715 (19) | 0.89413 (9) | 0.52551 (10) | 0.0234 (3) | |
C4B | 0.21711 (19) | 0.96697 (9) | 0.46849 (9) | 0.0228 (3) | |
H4BA | 0.2275 | 0.9743 | 0.4089 | 0.027* | |
C5B | 0.28120 (19) | 1.02872 (9) | 0.50258 (9) | 0.0218 (3) | |
C6B | 0.2675 (2) | 1.01959 (9) | 0.58902 (9) | 0.0241 (3) | |
H6BA | 0.3126 | 1.0637 | 0.6102 | 0.029* | |
C7B | 0.1768 (2) | 0.93243 (11) | 0.73967 (10) | 0.0305 (4) | |
O1C | 0.8772 (2) | 0.69194 (8) | 0.92314 (9) | 0.0544 (4) | |
O2C | 0.79118 (18) | 0.74970 (9) | 0.79701 (9) | 0.0510 (4) | |
O3C | 0.6006 (2) | 1.04864 (9) | 0.71583 (8) | 0.0550 (4) | |
O4C | 0.5860 (2) | 1.12038 (9) | 0.80821 (9) | 0.0622 (4) | |
O5C | 0.77940 (19) | 0.99684 (8) | 1.08784 (8) | 0.0456 (3) | |
H5 | 0.795 (3) | 0.9971 (16) | 1.1466 (17) | 0.088 (8)* | |
O6C | 0.9104 (2) | 0.86733 (9) | 1.12233 (9) | 0.0610 (4) | |
N1C | 0.82041 (19) | 0.75270 (9) | 0.86820 (10) | 0.0368 (4) | |
N2C | 0.6199 (2) | 1.05504 (10) | 0.78673 (9) | 0.0396 (4) | |
C1C | 0.7920 (2) | 0.91833 (10) | 0.98777 (10) | 0.0277 (4) | |
C2C | 0.8254 (2) | 0.84092 (10) | 0.96773 (10) | 0.0289 (4) | |
H2CA | 0.8743 | 0.7928 | 1.0075 | 0.035* | |
C3C | 0.7864 (2) | 0.83507 (10) | 0.88930 (10) | 0.0281 (4) | |
C4C | 0.7175 (2) | 0.90338 (11) | 0.82864 (10) | 0.0294 (4) | |
H4CA | 0.6916 | 0.8982 | 0.7747 | 0.035* | |
C5C | 0.6881 (2) | 0.97944 (10) | 0.85049 (10) | 0.0285 (4) | |
C6C | 0.7223 (2) | 0.98824 (10) | 0.92880 (10) | 0.0291 (4) | |
H6CA | 0.6984 | 1.0414 | 0.9420 | 0.035* | |
C7C | 0.8335 (2) | 0.92424 (11) | 1.07375 (11) | 0.0350 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0332 (6) | 0.0175 (5) | 0.0324 (6) | 0.0020 (5) | −0.0013 (5) | −0.0067 (5) |
O2 | 0.0262 (6) | 0.0291 (6) | 0.0355 (6) | −0.0001 (5) | −0.0036 (5) | −0.0107 (5) |
O3 | 0.0301 (6) | 0.0298 (6) | 0.0295 (6) | −0.0026 (5) | 0.0036 (5) | −0.0096 (5) |
O4 | 0.0306 (6) | 0.0296 (6) | 0.0403 (7) | 0.0022 (5) | −0.0023 (5) | −0.0183 (5) |
O5 | 0.0220 (6) | 0.0276 (6) | 0.0425 (7) | −0.0031 (4) | −0.0008 (5) | −0.0162 (5) |
O6 | 0.0345 (6) | 0.0215 (6) | 0.0358 (6) | 0.0004 (5) | 0.0025 (5) | −0.0103 (5) |
C1 | 0.0461 (10) | 0.0182 (8) | 0.0277 (9) | −0.0023 (7) | −0.0052 (7) | −0.0049 (7) |
C2 | 0.0407 (10) | 0.0222 (8) | 0.0342 (9) | −0.0081 (7) | −0.0089 (8) | −0.0051 (7) |
C3 | 0.0242 (9) | 0.0292 (9) | 0.0752 (14) | −0.0054 (7) | 0.0018 (9) | −0.0090 (10) |
C4 | 0.0349 (10) | 0.0362 (10) | 0.0565 (13) | −0.0002 (8) | 0.0205 (9) | −0.0040 (9) |
C5 | 0.0339 (10) | 0.0527 (11) | 0.0317 (9) | 0.0054 (8) | 0.0008 (8) | −0.0228 (9) |
C6 | 0.0341 (10) | 0.0415 (10) | 0.0465 (11) | 0.0053 (8) | −0.0047 (8) | −0.0292 (9) |
C7 | 0.0384 (10) | 0.0272 (9) | 0.0434 (10) | −0.0006 (7) | −0.0101 (8) | −0.0184 (8) |
C8 | 0.0332 (9) | 0.0271 (8) | 0.0422 (10) | −0.0059 (7) | −0.0103 (8) | −0.0143 (8) |
C9 | 0.0213 (8) | 0.0265 (9) | 0.0549 (12) | −0.0020 (7) | 0.0033 (8) | −0.0078 (8) |
C10 | 0.0299 (9) | 0.0305 (9) | 0.0428 (10) | 0.0007 (7) | 0.0102 (8) | −0.0082 (8) |
C11 | 0.0322 (9) | 0.0319 (9) | 0.0403 (10) | 0.0061 (7) | 0.0021 (8) | −0.0183 (8) |
C12 | 0.0343 (9) | 0.0233 (8) | 0.0402 (10) | 0.0070 (7) | −0.0064 (8) | −0.0139 (7) |
O1A | 0.0966 (12) | 0.0637 (10) | 0.0307 (7) | 0.0390 (9) | −0.0283 (7) | −0.0249 (7) |
O2A | 0.0598 (8) | 0.0307 (7) | 0.0275 (7) | 0.0119 (6) | −0.0175 (6) | −0.0048 (5) |
N1A | 0.0225 (7) | 0.0199 (7) | 0.0194 (6) | 0.0011 (5) | −0.0039 (5) | −0.0060 (5) |
C1A | 0.0223 (8) | 0.0267 (8) | 0.0199 (7) | 0.0022 (6) | −0.0003 (6) | −0.0060 (6) |
C2A | 0.0389 (10) | 0.0285 (9) | 0.0259 (8) | 0.0095 (7) | −0.0076 (7) | −0.0151 (7) |
C3A | 0.0339 (9) | 0.0202 (8) | 0.0271 (8) | 0.0063 (7) | −0.0057 (7) | −0.0094 (7) |
C4A | 0.0156 (7) | 0.0217 (7) | 0.0190 (7) | 0.0008 (6) | −0.0008 (6) | −0.0054 (6) |
C5A | 0.0271 (8) | 0.0196 (7) | 0.0244 (8) | 0.0009 (6) | −0.0038 (6) | −0.0097 (6) |
C6A | 0.0270 (8) | 0.0179 (7) | 0.0260 (8) | 0.0011 (6) | −0.0035 (6) | −0.0048 (6) |
C7A | 0.0310 (9) | 0.0331 (9) | 0.0229 (8) | 0.0044 (7) | −0.0032 (7) | −0.0070 (7) |
O1B | 0.1197 (14) | 0.0518 (9) | 0.0528 (9) | −0.0536 (9) | 0.0034 (9) | −0.0169 (8) |
O2B | 0.0728 (10) | 0.0584 (9) | 0.0429 (8) | −0.0199 (7) | −0.0012 (7) | −0.0330 (7) |
O3B | 0.0875 (10) | 0.0349 (7) | 0.0206 (6) | −0.0136 (7) | −0.0004 (6) | −0.0046 (5) |
O4B | 0.0634 (9) | 0.0291 (6) | 0.0348 (7) | −0.0174 (6) | −0.0102 (6) | −0.0058 (6) |
O5B | 0.1249 (14) | 0.0416 (8) | 0.0220 (7) | −0.0104 (8) | −0.0024 (8) | −0.0141 (6) |
O6B | 0.0465 (7) | 0.0349 (7) | 0.0231 (6) | −0.0009 (5) | −0.0073 (5) | 0.0012 (5) |
N1B | 0.0363 (8) | 0.0290 (8) | 0.0404 (9) | −0.0029 (6) | −0.0073 (7) | −0.0168 (7) |
N2B | 0.0383 (8) | 0.0206 (7) | 0.0250 (7) | 0.0018 (6) | −0.0047 (6) | −0.0055 (6) |
C1B | 0.0286 (8) | 0.0236 (8) | 0.0206 (8) | 0.0049 (6) | −0.0048 (6) | −0.0063 (6) |
C2B | 0.0241 (8) | 0.0207 (7) | 0.0270 (8) | 0.0017 (6) | −0.0021 (6) | −0.0058 (6) |
C3B | 0.0252 (8) | 0.0210 (7) | 0.0276 (8) | 0.0024 (6) | −0.0061 (6) | −0.0117 (6) |
C4B | 0.0272 (8) | 0.0237 (8) | 0.0202 (7) | 0.0066 (6) | −0.0065 (6) | −0.0095 (6) |
C5B | 0.0278 (8) | 0.0169 (7) | 0.0204 (7) | 0.0028 (6) | −0.0039 (6) | −0.0043 (6) |
C6B | 0.0310 (8) | 0.0200 (7) | 0.0237 (8) | 0.0038 (6) | −0.0072 (7) | −0.0090 (6) |
C7B | 0.0370 (9) | 0.0320 (9) | 0.0230 (8) | 0.0004 (7) | −0.0044 (7) | −0.0081 (7) |
O1C | 0.0822 (11) | 0.0285 (7) | 0.0540 (9) | 0.0153 (7) | −0.0014 (8) | −0.0156 (7) |
O2C | 0.0572 (9) | 0.0512 (8) | 0.0625 (9) | 0.0123 (7) | −0.0181 (7) | −0.0417 (8) |
O3C | 0.0865 (11) | 0.0552 (9) | 0.0285 (7) | 0.0216 (8) | −0.0179 (7) | −0.0178 (7) |
O4C | 0.1129 (13) | 0.0356 (8) | 0.0468 (8) | 0.0325 (8) | −0.0301 (8) | −0.0203 (7) |
O5C | 0.0786 (10) | 0.0354 (7) | 0.0283 (7) | 0.0097 (7) | −0.0097 (7) | −0.0168 (6) |
O6C | 0.1080 (13) | 0.0447 (8) | 0.0338 (7) | 0.0255 (8) | −0.0263 (8) | −0.0123 (7) |
N1C | 0.0383 (9) | 0.0304 (8) | 0.0475 (10) | 0.0030 (7) | 0.0016 (7) | −0.0218 (7) |
N2C | 0.0564 (10) | 0.0347 (8) | 0.0300 (8) | 0.0117 (7) | −0.0090 (7) | −0.0121 (7) |
C1C | 0.0344 (9) | 0.0259 (8) | 0.0235 (8) | −0.0002 (7) | 0.0006 (7) | −0.0090 (7) |
C2C | 0.0333 (9) | 0.0247 (8) | 0.0279 (9) | 0.0025 (7) | 0.0011 (7) | −0.0074 (7) |
C3C | 0.0287 (9) | 0.0256 (8) | 0.0339 (9) | 0.0009 (7) | 0.0035 (7) | −0.0164 (7) |
C4C | 0.0303 (9) | 0.0347 (9) | 0.0272 (8) | 0.0014 (7) | −0.0012 (7) | −0.0156 (7) |
C5C | 0.0346 (9) | 0.0258 (8) | 0.0260 (8) | 0.0058 (7) | −0.0030 (7) | −0.0089 (7) |
C6C | 0.0413 (10) | 0.0224 (8) | 0.0259 (8) | 0.0018 (7) | 0.0005 (7) | −0.0114 (7) |
C7C | 0.0514 (11) | 0.0272 (9) | 0.0257 (9) | 0.0002 (8) | −0.0017 (8) | −0.0069 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.4260 (18) | C1A—C6A | 1.385 (2) |
O1—C12 | 1.4280 (19) | C1A—C2A | 1.385 (2) |
O2—C3 | 1.417 (2) | C1A—C7A | 1.496 (2) |
O2—C2 | 1.4279 (19) | C2A—C3A | 1.383 (2) |
O3—C4 | 1.423 (2) | C2A—H2AA | 0.9500 |
O3—C5 | 1.4276 (19) | C3A—C4A | 1.383 (2) |
O4—C6 | 1.424 (2) | C3A—H3AA | 0.9500 |
O4—C7 | 1.4291 (19) | C4A—C5A | 1.381 (2) |
O5—C8 | 1.4249 (18) | C5A—C6A | 1.386 (2) |
O5—C9 | 1.4261 (19) | C5A—H5AA | 0.9500 |
O6—C10 | 1.4220 (19) | C6A—H6AA | 0.9500 |
O6—C11 | 1.4277 (18) | O1B—N1B | 1.2096 (19) |
C1—C2 | 1.490 (2) | O2B—N1B | 1.2087 (18) |
C1—H1A | 0.9900 | O3B—N2B | 1.2187 (17) |
C1—H1B | 0.9900 | O4B—N2B | 1.2188 (16) |
C2—H2A | 0.9900 | O5B—C7B | 1.243 (2) |
C2—H2B | 0.9900 | O6B—C7B | 1.2428 (19) |
C3—C4 | 1.491 (3) | N1B—C3B | 1.4738 (19) |
C3—H3A | 0.9900 | N2B—C5B | 1.4710 (19) |
C3—H3B | 0.9900 | C1B—C6B | 1.387 (2) |
C4—H4A | 0.9900 | C1B—C2B | 1.388 (2) |
C4—H4B | 0.9900 | C1B—C7B | 1.518 (2) |
C5—C6 | 1.495 (2) | C2B—C3B | 1.382 (2) |
C5—H5A | 0.9900 | C2B—H2BA | 0.9500 |
C5—H5B | 0.9900 | C3B—C4B | 1.378 (2) |
C6—H6A | 0.9900 | C4B—C5B | 1.379 (2) |
C6—H6B | 0.9900 | C4B—H4BA | 0.9500 |
C7—C8 | 1.493 (2) | C5B—C6B | 1.382 (2) |
C7—H7A | 0.9900 | C6B—H6BA | 0.9500 |
C7—H7B | 0.9900 | O1C—N1C | 1.2226 (19) |
C8—H8A | 0.9900 | O2C—N1C | 1.2231 (19) |
C8—H8B | 0.9900 | O3C—N2C | 1.2199 (18) |
C9—C10 | 1.499 (2) | O4C—N2C | 1.2176 (18) |
C9—H9A | 0.9900 | O5C—C7C | 1.307 (2) |
C9—H9B | 0.9900 | O5C—H5 | 0.98 (3) |
C10—H10A | 0.9900 | O6C—C7C | 1.206 (2) |
C10—H10B | 0.9900 | N1C—C3C | 1.475 (2) |
C11—C12 | 1.496 (2) | N2C—C5C | 1.474 (2) |
C11—H11A | 0.9900 | C1C—C6C | 1.384 (2) |
C11—H11B | 0.9900 | C1C—C2C | 1.389 (2) |
C12—H12A | 0.9900 | C1C—C7C | 1.502 (2) |
C12—H12B | 0.9900 | C2C—C3C | 1.375 (2) |
O1A—C7A | 1.2023 (19) | C2C—H2CA | 0.9500 |
O2A—C7A | 1.315 (2) | C3C—C4C | 1.381 (2) |
O2A—H2 | 0.87 (2) | C4C—C5C | 1.378 (2) |
N1A—C4A | 1.4641 (18) | C4C—H4CA | 0.9500 |
N1A—H1AA | 0.942 (19) | C5C—C6C | 1.380 (2) |
N1A—H1AB | 0.97 (2) | C6C—H6CA | 0.9500 |
N1A—H1AC | 0.94 (2) | | |
| | | |
C1—O1—C12 | 113.04 (11) | H1AA—N1A—H1AB | 108.1 (16) |
C3—O2—C2 | 111.90 (13) | C4A—N1A—H1AC | 108.4 (12) |
C4—O3—C5 | 111.99 (13) | H1AA—N1A—H1AC | 111.5 (17) |
C6—O4—C7 | 111.62 (12) | H1AB—N1A—H1AC | 106.1 (17) |
C8—O5—C9 | 111.72 (12) | C6A—C1A—C2A | 119.55 (14) |
C10—O6—C11 | 113.34 (13) | C6A—C1A—C7A | 122.39 (14) |
O1—C1—C2 | 108.20 (12) | C2A—C1A—C7A | 118.04 (14) |
O1—C1—H1A | 110.1 | C3A—C2A—C1A | 120.95 (14) |
C2—C1—H1A | 110.1 | C3A—C2A—H2AA | 119.5 |
O1—C1—H1B | 110.1 | C1A—C2A—H2AA | 119.5 |
C2—C1—H1B | 110.1 | C4A—C3A—C2A | 118.59 (14) |
H1A—C1—H1B | 108.4 | C4A—C3A—H3AA | 120.7 |
O2—C2—C1 | 108.83 (13) | C2A—C3A—H3AA | 120.7 |
O2—C2—H2A | 109.9 | C5A—C4A—C3A | 121.41 (13) |
C1—C2—H2A | 109.9 | C5A—C4A—N1A | 118.52 (13) |
O2—C2—H2B | 109.9 | C3A—C4A—N1A | 120.05 (13) |
C1—C2—H2B | 109.9 | C4A—C5A—C6A | 119.27 (14) |
H2A—C2—H2B | 108.3 | C4A—C5A—H5AA | 120.4 |
O2—C3—C4 | 109.08 (15) | C6A—C5A—H5AA | 120.4 |
O2—C3—H3A | 109.9 | C1A—C6A—C5A | 120.18 (14) |
C4—C3—H3A | 109.9 | C1A—C6A—H6AA | 119.9 |
O2—C3—H3B | 109.9 | C5A—C6A—H6AA | 119.9 |
C4—C3—H3B | 109.9 | O1A—C7A—O2A | 124.69 (15) |
H3A—C3—H3B | 108.3 | O1A—C7A—C1A | 122.28 (15) |
O3—C4—C3 | 110.02 (15) | O2A—C7A—C1A | 113.03 (14) |
O3—C4—H4A | 109.7 | O2B—N1B—O1B | 123.53 (15) |
C3—C4—H4A | 109.7 | O2B—N1B—C3B | 118.40 (14) |
O3—C4—H4B | 109.7 | O1B—N1B—C3B | 118.07 (14) |
C3—C4—H4B | 109.7 | O3B—N2B—O4B | 123.75 (14) |
H4A—C4—H4B | 108.2 | O3B—N2B—C5B | 118.22 (13) |
O3—C5—C6 | 109.32 (13) | O4B—N2B—C5B | 118.03 (13) |
O3—C5—H5A | 109.8 | C6B—C1B—C2B | 120.01 (14) |
C6—C5—H5A | 109.8 | C6B—C1B—C7B | 119.58 (14) |
O3—C5—H5B | 109.8 | C2B—C1B—C7B | 120.38 (14) |
C6—C5—H5B | 109.8 | C3B—C2B—C1B | 118.55 (14) |
H5A—C5—H5B | 108.3 | C3B—C2B—H2BA | 120.7 |
O4—C6—C5 | 108.80 (14) | C1B—C2B—H2BA | 120.7 |
O4—C6—H6A | 109.9 | C4B—C3B—C2B | 123.26 (14) |
C5—C6—H6A | 109.9 | C4B—C3B—N1B | 117.76 (13) |
O4—C6—H6B | 109.9 | C2B—C3B—N1B | 118.97 (14) |
C5—C6—H6B | 109.9 | C3B—C4B—C5B | 116.41 (13) |
H6A—C6—H6B | 108.3 | C3B—C4B—H4BA | 121.8 |
O4—C7—C8 | 109.02 (13) | C5B—C4B—H4BA | 121.8 |
O4—C7—H7A | 109.9 | C4B—C5B—C6B | 122.84 (14) |
C8—C7—H7A | 109.9 | C4B—C5B—N2B | 118.38 (13) |
O4—C7—H7B | 109.9 | C6B—C5B—N2B | 118.77 (13) |
C8—C7—H7B | 109.9 | C5B—C6B—C1B | 118.93 (14) |
H7A—C7—H7B | 108.3 | C5B—C6B—H6BA | 120.5 |
O5—C8—C7 | 108.95 (13) | C1B—C6B—H6BA | 120.5 |
O5—C8—H8A | 109.9 | O5B—C7B—O6B | 127.95 (16) |
C7—C8—H8A | 109.9 | O5B—C7B—C1B | 115.49 (14) |
O5—C8—H8B | 109.9 | O6B—C7B—C1B | 116.55 (14) |
C7—C8—H8B | 109.9 | C7C—O5C—H5 | 111.7 (14) |
H8A—C8—H8B | 108.3 | O1C—N1C—O2C | 124.33 (14) |
O5—C9—C10 | 109.13 (13) | O1C—N1C—C3C | 117.58 (15) |
O5—C9—H9A | 109.9 | O2C—N1C—C3C | 118.09 (15) |
C10—C9—H9A | 109.9 | O4C—N2C—O3C | 123.84 (15) |
O5—C9—H9B | 109.9 | O4C—N2C—C5C | 117.78 (14) |
C10—C9—H9B | 109.9 | O3C—N2C—C5C | 118.38 (14) |
H9A—C9—H9B | 108.3 | C6C—C1C—C2C | 119.94 (15) |
O6—C10—C9 | 108.64 (14) | C6C—C1C—C7C | 121.31 (14) |
O6—C10—H10A | 110.0 | C2C—C1C—C7C | 118.75 (15) |
C9—C10—H10A | 110.0 | C3C—C2C—C1C | 118.91 (15) |
O6—C10—H10B | 110.0 | C3C—C2C—H2CA | 120.5 |
C9—C10—H10B | 110.0 | C1C—C2C—H2CA | 120.5 |
H10A—C10—H10B | 108.3 | C2C—C3C—C4C | 122.91 (14) |
O6—C11—C12 | 108.56 (13) | C2C—C3C—N1C | 118.97 (15) |
O6—C11—H11A | 110.0 | C4C—C3C—N1C | 118.12 (15) |
C12—C11—H11A | 110.0 | C5C—C4C—C3C | 116.48 (15) |
O6—C11—H11B | 110.0 | C5C—C4C—H4CA | 121.8 |
C12—C11—H11B | 110.0 | C3C—C4C—H4CA | 121.8 |
H11A—C11—H11B | 108.4 | C4C—C5C—C6C | 122.89 (15) |
O1—C12—C11 | 108.01 (12) | C4C—C5C—N2C | 118.40 (14) |
O1—C12—H12A | 110.1 | C6C—C5C—N2C | 118.70 (14) |
C11—C12—H12A | 110.1 | C5C—C6C—C1C | 118.86 (14) |
O1—C12—H12B | 110.1 | C5C—C6C—H6CA | 120.6 |
C11—C12—H12B | 110.1 | C1C—C6C—H6CA | 120.6 |
H12A—C12—H12B | 108.4 | O6C—C7C—O5C | 125.45 (16) |
C7A—O2A—H2 | 107.8 (15) | O6C—C7C—C1C | 121.97 (15) |
C4A—N1A—H1AA | 108.8 (11) | O5C—C7C—C1C | 112.57 (15) |
C4A—N1A—H1AB | 113.9 (13) | | |
| | | |
C12—O1—C1—C2 | −172.39 (13) | C2B—C3B—C4B—C5B | −0.5 (2) |
C3—O2—C2—C1 | 179.13 (14) | N1B—C3B—C4B—C5B | −179.23 (13) |
O1—C1—C2—O2 | −64.66 (16) | C3B—C4B—C5B—C6B | 0.0 (2) |
C2—O2—C3—C4 | 176.87 (14) | C3B—C4B—C5B—N2B | 179.11 (13) |
C5—O3—C4—C3 | −175.63 (15) | O3B—N2B—C5B—C4B | 7.9 (2) |
O2—C3—C4—O3 | 65.0 (2) | O4B—N2B—C5B—C4B | −171.20 (14) |
C4—O3—C5—C6 | −177.92 (14) | O3B—N2B—C5B—C6B | −172.92 (15) |
C7—O4—C6—C5 | −174.48 (13) | O4B—N2B—C5B—C6B | 8.0 (2) |
O3—C5—C6—O4 | −61.86 (18) | C4B—C5B—C6B—C1B | 0.4 (2) |
C6—O4—C7—C8 | −176.84 (14) | N2B—C5B—C6B—C1B | −178.74 (13) |
C9—O5—C8—C7 | 165.93 (13) | C2B—C1B—C6B—C5B | −0.2 (2) |
O4—C7—C8—O5 | 58.47 (18) | C7B—C1B—C6B—C5B | 177.77 (14) |
C8—O5—C9—C10 | 173.09 (14) | C6B—C1B—C7B—O5B | 20.2 (2) |
C11—O6—C10—C9 | −169.38 (13) | C2B—C1B—C7B—O5B | −161.81 (16) |
O5—C9—C10—O6 | −62.57 (17) | C6B—C1B—C7B—O6B | −159.23 (15) |
C10—O6—C11—C12 | −173.00 (13) | C2B—C1B—C7B—O6B | 18.8 (2) |
C1—O1—C12—C11 | 170.27 (13) | C6C—C1C—C2C—C3C | −0.7 (2) |
O6—C11—C12—O1 | 61.15 (17) | C7C—C1C—C2C—C3C | 179.54 (15) |
C6A—C1A—C2A—C3A | 1.5 (2) | C1C—C2C—C3C—C4C | 1.0 (2) |
C7A—C1A—C2A—C3A | −177.11 (15) | C1C—C2C—C3C—N1C | −179.52 (14) |
C1A—C2A—C3A—C4A | −1.4 (2) | O1C—N1C—C3C—C2C | 2.3 (2) |
C2A—C3A—C4A—C5A | −0.1 (2) | O2C—N1C—C3C—C2C | −177.30 (15) |
C2A—C3A—C4A—N1A | −178.75 (14) | O1C—N1C—C3C—C4C | −178.20 (15) |
C3A—C4A—C5A—C6A | 1.5 (2) | O2C—N1C—C3C—C4C | 2.2 (2) |
N1A—C4A—C5A—C6A | −179.85 (13) | C2C—C3C—C4C—C5C | −0.2 (2) |
C2A—C1A—C6A—C5A | −0.1 (2) | N1C—C3C—C4C—C5C | −179.73 (14) |
C7A—C1A—C6A—C5A | 178.46 (14) | C3C—C4C—C5C—C6C | −0.9 (2) |
C4A—C5A—C6A—C1A | −1.4 (2) | C3C—C4C—C5C—N2C | 178.10 (15) |
C6A—C1A—C7A—O1A | 169.77 (17) | O4C—N2C—C5C—C4C | 176.31 (17) |
C2A—C1A—C7A—O1A | −11.7 (2) | O3C—N2C—C5C—C4C | −3.6 (2) |
C6A—C1A—C7A—O2A | −10.8 (2) | O4C—N2C—C5C—C6C | −4.7 (2) |
C2A—C1A—C7A—O2A | 167.74 (14) | O3C—N2C—C5C—C6C | 175.40 (16) |
C6B—C1B—C2B—C3B | −0.3 (2) | C4C—C5C—C6C—C1C | 1.1 (3) |
C7B—C1B—C2B—C3B | −178.26 (14) | N2C—C5C—C6C—C1C | −177.83 (15) |
C1B—C2B—C3B—C4B | 0.7 (2) | C2C—C1C—C6C—C5C | −0.3 (2) |
C1B—C2B—C3B—N1B | 179.37 (13) | C7C—C1C—C6C—C5C | 179.46 (15) |
O2B—N1B—C3B—C4B | 4.4 (2) | C6C—C1C—C7C—O6C | −172.35 (18) |
O1B—N1B—C3B—C4B | −175.29 (16) | C2C—C1C—C7C—O6C | 7.4 (3) |
O2B—N1B—C3B—C2B | −174.40 (15) | C6C—C1C—C7C—O5C | 6.8 (2) |
O1B—N1B—C3B—C2B | 6.0 (2) | C2C—C1C—C7C—O5C | −173.40 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1 | 0.942 (19) | 1.89 (2) | 2.8267 (17) | 172.6 (16) |
N1A—H1AA···O2 | 0.942 (19) | 2.545 (18) | 2.9607 (17) | 107.0 (13) |
N1A—H1AB···O3 | 0.97 (2) | 1.92 (2) | 2.8811 (17) | 171.5 (19) |
N1A—H1AC···O4 | 0.94 (2) | 2.53 (2) | 3.0035 (17) | 111.4 (14) |
N1A—H1AC···O5 | 0.94 (2) | 1.85 (2) | 2.7639 (17) | 163.6 (18) |
O2A—H2···O6Bi | 0.87 (2) | 1.72 (2) | 2.5883 (16) | 176 (2) |
O5C—H5···O5Bii | 0.98 (3) | 1.54 (3) | 2.5208 (17) | 175 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+2. |
Experimental details
| (1) | (2) |
Crystal data |
Chemical formula | C12H24O6·2(C7H7NO2) | C12H24O6·C7H3N2O6·C7H4N2O6·C7H8NO2 |
Mr | 538.58 | 825.69 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 173 | 173 |
a, b, c (Å) | 10.3947 (3), 17.5546 (5), 47.2700 (14) | 7.6055 (2), 16.0157 (4), 16.4476 (4) |
α, β, γ (°) | 90, 91.321 (2), 90 | 73.156 (2), 85.540 (2), 89.562 (1) |
V (Å3) | 8623.3 (4) | 1911.45 (9) |
Z | 12 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.12 |
Crystal size (mm) | 0.79 × 0.65 × 0.53 | 0.24 × 0.21 × 0.17 |
|
Data collection |
Diffractometer | Bruker APEX-II CCD diffractometer | Bruker APEX-II CCD diffractometer |
Absorption correction | Multi-scan SADABS (Bruker, 2008) | Multi-scan SADABS (Bruker, 2008) |
Tmin, Tmax | 0.928, 0.950 | 0.971, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 132140, 16030, 10452 | 50498, 10356, 6336 |
Rint | 0.045 | 0.047 |
(sin θ/λ)max (Å−1) | 0.620 | 0.703 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.199, 1.06 | 0.047, 0.112, 1.01 |
No. of reflections | 16030 | 10356 |
No. of parameters | 1114 | 543 |
No. of restraints | 6 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
| w = 1/[σ2(Fo2) + (0.0614P)2 + 16.5586P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0438P)2 + 0.335P] where P = (Fo2 + 2Fc2)/3 |
Δρmax, Δρmin (e Å−3) | 0.91, −0.37 | 0.29, −0.27 |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12A—H12A···O2Bi | 0.99 | 2.65 | 3.550 (5) | 151.2 |
O1B—H1B···O2Bii | 1.04 (6) | 1.57 (6) | 2.604 (4) | 175 (5) |
N1B—H1BA···O6I | 0.85 (5) | 2.37 (5) | 3.138 (5) | 150 (4) |
N1B—H1BB···O2I | 0.86 (6) | 2.60 (5) | 3.280 (5) | 138 (4) |
N1B—H1BB···O3I | 0.86 (6) | 2.27 (6) | 3.061 (5) | 154 (5) |
O1C—H1C···O2D | 1.01 (5) | 1.60 (6) | 2.600 (3) | 170 (5) |
N1C—H1CA···O4Aiii | 0.83 (5) | 2.58 (5) | 3.153 (5) | 127 (4) |
N1C—H1CA···O5Aiii | 0.83 (5) | 2.25 (5) | 3.055 (5) | 164 (4) |
N1C—H1CB···O1Aiii | 0.81 (5) | 2.25 (5) | 2.998 (5) | 153 (5) |
O1D—H1D···O2C | 0.84 | 1.78 | 2.617 (3) | 172.1 |
N1D—H1DA···O4Hiv | 0.85 (5) | 2.23 (5) | 2.961 (4) | 144 (5) |
N1D—H1DB···O5Hiv | 0.86 (5) | 2.64 (5) | 3.102 (4) | 114 (4) |
N1D—H1DB···O6Hiv | 0.86 (5) | 2.30 (5) | 3.148 (5) | 165 (4) |
O1E—H1E···O2Ev | 1.12 (6) | 1.50 (7) | 2.622 (3) | 172 (5) |
N1E—H1EA···O1H | 0.89 (4) | 2.30 (4) | 3.069 (4) | 144 (3) |
N1E—H1EA···O2H | 0.89 (4) | 2.63 (4) | 3.403 (5) | 147 (3) |
N1E—H1EB···O5H | 0.82 (4) | 2.33 (5) | 3.125 (5) | 162 (4) |
O1F—H1F···O1G | 1.17 (7) | 2.64 (7) | 3.483 (4) | 128 (4) |
O1F—H1F···O2G | 1.17 (7) | 1.44 (7) | 2.600 (3) | 171 (6) |
O2G—H1F···O2F | 1.44 (7) | 2.42 (7) | 3.370 (4) | 119 (4) |
N1F—H1FA···O3I | 0.87 (4) | 2.33 (4) | 3.083 (5) | 145 (4) |
N1F—H1FA···O4I | 0.87 (4) | 2.63 (4) | 3.380 (5) | 145 (3) |
N1F—H1FB···O1I | 0.80 (6) | 2.41 (6) | 3.165 (5) | 159 (5) |
N1F—H1FB···O6I | 0.80 (6) | 2.65 (6) | 3.215 (5) | 129 (5) |
O2F—H1G···O2G | 1.35 (7) | 2.50 (7) | 3.370 (4) | 119 (4) |
O1G—H1G···O1F | 1.25 (7) | 2.62 (7) | 3.483 (4) | 124 (4) |
O1G—H1G···O2F | 1.25 (7) | 1.35 (7) | 2.604 (3) | 177 (6) |
N1G—H1GA···O6Avi | 0.84 (4) | 2.24 (4) | 3.058 (5) | 168 (3) |
N1G—H1GB···O3Avi | 0.82 (5) | 2.59 (5) | 3.353 (5) | 156 (4) |
N1G—H1GB···O4Avi | 0.82 (5) | 2.41 (5) | 3.058 (4) | 136 (4) |
C3H—H3HB···O2Cvii | 0.99 | 2.63 | 3.504 (5) | 147.7 |
C7I—H7IA···O2D | 0.99 | 2.53 | 3.494 (6) | 164.0 |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+1, −z; (vi) −x+1/2, y+1/2, −z+1/2; (vii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (2) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1 | 0.942 (19) | 1.89 (2) | 2.8267 (17) | 172.6 (16) |
N1A—H1AA···O2 | 0.942 (19) | 2.545 (18) | 2.9607 (17) | 107.0 (13) |
N1A—H1AB···O3 | 0.97 (2) | 1.92 (2) | 2.8811 (17) | 171.5 (19) |
N1A—H1AC···O4 | 0.94 (2) | 2.53 (2) | 3.0035 (17) | 111.4 (14) |
N1A—H1AC···O5 | 0.94 (2) | 1.85 (2) | 2.7639 (17) | 163.6 (18) |
O2A—H2···O6Bi | 0.87 (2) | 1.72 (2) | 2.5883 (16) | 176 (2) |
O5C—H5···O5Bii | 0.98 (3) | 1.54 (3) | 2.5208 (17) | 175 (2) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+2, −z+2. |