In the title compound, 2C
5H
6N
5+·C
8H
4O
42−·C
8H
6O
4·1.45H
2O, the asymmetric unit comprises two adeninium cations, two half phthalate anions with crystallographic
C2 symmetry, one neutral phthalic acid molecule, and one fully occupied and one partially occupied site (0.45) for water molecules. The adeninium cations form N—H
O hydrogen bonds with the phthalate anions. The cations also form infinite one-dimensional polymeric ribbons
via N—H
N interactions. In the crystal packing, hydrogen-bonded columns of cations, anions and phthalate anions extend parallel to the
c axis. The water molecules crosslink adjacent columns into hydrogen-bonded layers.
Supporting information
CCDC reference: 645568
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and DIAMOND (Brandenburg & Putz,
2005); software used to prepare material for publication: SHELXL97.
bis(adeninium) phthalate phthalic acid 1.45-hydrate
top
Crystal data top
2C5H6N5+·C8H4O42−·C8H6O4·1.45H2O | F(000) = 2612.1 |
Mr = 628.65 | Dx = 1.486 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 7507 reflections |
a = 7.0100 (5) Å | θ = 2.5–27.5° |
b = 33.052 (2) Å | µ = 0.12 mm−1 |
c = 24.2496 (17) Å | T = 293 K |
V = 5618.4 (7) Å3 | Block, colourless |
Z = 8 | 0.19 × 0.17 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4499 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω scans | h = −8→8 |
50712 measured reflections | k = −39→39 |
4961 independent reflections | l = −28→28 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0485P)2 + 2.4152P] where P = (Fo2 + 2Fc2)/3 |
4961 reflections | (Δ/σ)max = 0.001 |
472 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.20 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5854 (2) | 0.63643 (5) | 0.69324 (6) | 0.0371 (4) | |
C2 | 0.5315 (2) | 0.67455 (4) | 0.72261 (6) | 0.0333 (3) | |
C3 | 0.5612 (2) | 0.71129 (5) | 0.69591 (7) | 0.0389 (4) | |
H3 | 0.6020 | 0.7115 | 0.6594 | 0.047* | |
C4 | 0.5309 (2) | 0.74746 (5) | 0.72305 (7) | 0.0439 (4) | |
H4 | 0.5521 | 0.7718 | 0.7049 | 0.053* | |
O1 | 0.6818 (2) | 0.61093 (4) | 0.72005 (5) | 0.0599 (4) | |
O2 | 0.5425 (2) | 0.63196 (4) | 0.64362 (4) | 0.0508 (3) | |
C5 | 0.6074 (2) | 0.68901 (5) | 0.30215 (6) | 0.0373 (4) | |
C6 | 0.5388 (2) | 0.72766 (4) | 0.27660 (6) | 0.0329 (3) | |
C7 | 0.5711 (2) | 0.76419 (5) | 0.30321 (7) | 0.0408 (4) | |
H7 | 0.6177 | 0.7643 | 0.3391 | 0.049* | |
C8 | 0.5342 (2) | 0.80036 (5) | 0.27662 (7) | 0.0470 (4) | |
H8A | 0.5555 | 0.8247 | 0.2947 | 0.056* | |
O3 | 0.7061 (2) | 0.66571 (4) | 0.27305 (5) | 0.0593 (4) | |
O4 | 0.57341 (19) | 0.68209 (4) | 0.35207 (4) | 0.0485 (3) | |
C9 | 0.1690 (3) | 0.64747 (5) | 0.55479 (7) | 0.0440 (4) | |
C10 | 0.0225 (3) | 0.67218 (5) | 0.52441 (6) | 0.0397 (4) | |
C11 | −0.1510 (3) | 0.67834 (6) | 0.55067 (8) | 0.0514 (5) | |
H11 | −0.1723 | 0.6670 | 0.5852 | 0.062* | |
C12 | −0.2918 (3) | 0.70108 (6) | 0.52600 (8) | 0.0573 (5) | |
H12 | −0.4075 | 0.7050 | 0.5440 | 0.069* | |
C13 | −0.2625 (3) | 0.71805 (6) | 0.47484 (8) | 0.0538 (5) | |
H13 | −0.3582 | 0.7333 | 0.4583 | 0.065* | |
C14 | −0.0911 (3) | 0.71237 (5) | 0.44834 (7) | 0.0457 (4) | |
H14 | −0.0714 | 0.7239 | 0.4138 | 0.055* | |
C15 | 0.0533 (2) | 0.68956 (5) | 0.47258 (6) | 0.0377 (4) | |
C16 | 0.2374 (2) | 0.68309 (5) | 0.44358 (6) | 0.0388 (4) | |
O5 | 0.1742 (3) | 0.61115 (4) | 0.55338 (6) | 0.0723 (5) | |
O6 | 0.2806 (2) | 0.67018 (4) | 0.58560 (5) | 0.0537 (3) | |
H6 | 0.371 (4) | 0.6559 (8) | 0.6060 (11) | 0.098 (9)* | |
O7 | 0.34442 (19) | 0.65565 (4) | 0.45513 (6) | 0.0577 (4) | |
O8 | 0.2722 (2) | 0.70943 (4) | 0.40411 (5) | 0.0519 (3) | |
H8 | 0.377 (4) | 0.7014 (7) | 0.3871 (10) | 0.078 (8)* | |
C22 | 0.6827 (3) | 0.60099 (6) | 0.44488 (7) | 0.0477 (4) | |
H22 | 0.6684 | 0.6235 | 0.4675 | 0.057* | |
C24 | 0.7242 (2) | 0.53533 (5) | 0.43201 (7) | 0.0421 (4) | |
C25 | 0.7202 (3) | 0.53809 (5) | 0.37511 (7) | 0.0419 (4) | |
C26 | 0.6955 (2) | 0.57644 (5) | 0.35165 (7) | 0.0415 (4) | |
C28 | 0.7573 (3) | 0.47633 (6) | 0.39350 (7) | 0.0510 (5) | |
H28 | 0.7737 | 0.4485 | 0.3901 | 0.061* | |
N21 | 0.6757 (2) | 0.60705 (4) | 0.38999 (6) | 0.0428 (3) | |
H21 | 0.654 (3) | 0.6328 (7) | 0.3787 (9) | 0.063 (6)* | |
N23 | 0.7080 (2) | 0.56618 (5) | 0.46895 (6) | 0.0483 (4) | |
N27 | 0.7411 (2) | 0.50069 (4) | 0.35094 (6) | 0.0486 (4) | |
N29 | 0.7477 (2) | 0.49560 (5) | 0.44302 (6) | 0.0481 (4) | |
H29 | 0.759 (3) | 0.4856 (7) | 0.4783 (9) | 0.066 (6)* | |
N30 | 0.6889 (3) | 0.58450 (5) | 0.29864 (6) | 0.0533 (4) | |
H301 | 0.685 (3) | 0.6107 (8) | 0.2880 (9) | 0.070 (7)* | |
H302 | 0.716 (3) | 0.5655 (6) | 0.2747 (8) | 0.050 (5)* | |
C32 | 0.7465 (3) | 0.50949 (5) | 0.71608 (7) | 0.0505 (5) | |
H32 | 0.7425 | 0.5170 | 0.7530 | 0.061* | |
C34 | 0.7801 (2) | 0.46369 (5) | 0.65045 (7) | 0.0387 (4) | |
C35 | 0.7599 (2) | 0.49169 (5) | 0.60869 (6) | 0.0366 (3) | |
C36 | 0.7271 (2) | 0.53230 (5) | 0.62354 (6) | 0.0386 (4) | |
C38 | 0.7983 (3) | 0.43451 (5) | 0.57031 (7) | 0.0444 (4) | |
H38 | 0.8119 | 0.4143 | 0.5439 | 0.053* | |
N31 | 0.7239 (2) | 0.53911 (4) | 0.67878 (6) | 0.0444 (4) | |
H31 | 0.706 (4) | 0.5654 (6) | 0.6913 (10) | 0.089 (8)* | |
N33 | 0.7737 (2) | 0.47103 (4) | 0.70546 (6) | 0.0494 (4) | |
N37 | 0.7711 (2) | 0.47273 (4) | 0.55777 (5) | 0.0427 (3) | |
N39 | 0.8046 (2) | 0.42725 (4) | 0.62520 (6) | 0.0430 (3) | |
H39 | 0.829 (3) | 0.4036 (7) | 0.6430 (8) | 0.058 (6)* | |
N40 | 0.6988 (3) | 0.56279 (5) | 0.58987 (6) | 0.0520 (4) | |
H401 | 0.670 (3) | 0.5864 (7) | 0.6031 (8) | 0.059 (6)* | |
H402 | 0.704 (3) | 0.5597 (6) | 0.5510 (9) | 0.061 (6)* | |
O1W | 0.9041 (3) | 0.35656 (4) | 0.67902 (6) | 0.0587 (4) | |
H1W | 0.824 (5) | 0.3480 (10) | 0.7030 (13) | 0.108 (11)* | |
H2W | 1.012 (6) | 0.3530 (11) | 0.6923 (16) | 0.151 (16)* | |
O2W | 1.0978 (8) | 0.59414 (17) | 0.6871 (2) | 0.104 (2) | 0.454 (6) |
H3W | 1.194 (7) | 0.605 (2) | 0.706 (3) | 0.14 (3)* | 0.454 (6) |
H4W | 0.992 (7) | 0.591 (4) | 0.707 (3) | 0.24 (7)* | 0.454 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0429 (9) | 0.0348 (8) | 0.0337 (8) | 0.0032 (7) | −0.0003 (7) | 0.0015 (6) |
C2 | 0.0337 (8) | 0.0308 (7) | 0.0352 (8) | 0.0004 (6) | −0.0037 (6) | 0.0014 (6) |
C3 | 0.0398 (9) | 0.0379 (8) | 0.0392 (8) | −0.0003 (7) | −0.0022 (7) | 0.0076 (7) |
C4 | 0.0449 (10) | 0.0293 (8) | 0.0576 (10) | −0.0024 (7) | −0.0087 (8) | 0.0079 (7) |
O1 | 0.0904 (10) | 0.0429 (7) | 0.0465 (7) | 0.0276 (7) | −0.0217 (7) | −0.0100 (6) |
O2 | 0.0717 (9) | 0.0484 (7) | 0.0323 (6) | 0.0172 (6) | −0.0052 (6) | −0.0045 (5) |
C5 | 0.0403 (9) | 0.0377 (8) | 0.0340 (8) | 0.0036 (7) | 0.0051 (7) | 0.0003 (6) |
C6 | 0.0335 (8) | 0.0324 (8) | 0.0328 (7) | 0.0012 (6) | 0.0065 (6) | −0.0002 (6) |
C7 | 0.0384 (9) | 0.0426 (9) | 0.0413 (9) | 0.0005 (7) | 0.0025 (7) | −0.0088 (7) |
C8 | 0.0439 (10) | 0.0309 (8) | 0.0662 (11) | −0.0016 (7) | 0.0075 (8) | −0.0096 (7) |
O3 | 0.0851 (10) | 0.0430 (7) | 0.0498 (7) | 0.0247 (7) | 0.0280 (7) | 0.0095 (6) |
O4 | 0.0647 (8) | 0.0486 (7) | 0.0320 (6) | 0.0125 (6) | 0.0077 (6) | 0.0052 (5) |
C9 | 0.0573 (11) | 0.0399 (9) | 0.0347 (8) | −0.0002 (8) | 0.0045 (8) | 0.0025 (7) |
C10 | 0.0477 (9) | 0.0346 (8) | 0.0367 (8) | −0.0043 (7) | 0.0018 (7) | −0.0043 (6) |
C11 | 0.0561 (11) | 0.0533 (11) | 0.0448 (10) | −0.0037 (9) | 0.0109 (9) | −0.0038 (8) |
C12 | 0.0451 (11) | 0.0648 (12) | 0.0620 (12) | 0.0014 (9) | 0.0108 (9) | −0.0146 (10) |
C13 | 0.0455 (10) | 0.0559 (11) | 0.0599 (12) | 0.0095 (9) | −0.0082 (9) | −0.0107 (9) |
C14 | 0.0497 (10) | 0.0459 (9) | 0.0416 (9) | 0.0023 (8) | −0.0057 (8) | −0.0021 (7) |
C15 | 0.0422 (9) | 0.0353 (8) | 0.0357 (8) | −0.0017 (7) | −0.0012 (7) | −0.0036 (6) |
C16 | 0.0456 (9) | 0.0364 (8) | 0.0344 (8) | 0.0002 (7) | −0.0008 (7) | −0.0021 (7) |
O5 | 0.1073 (13) | 0.0387 (8) | 0.0708 (10) | 0.0008 (8) | −0.0185 (9) | 0.0078 (6) |
O6 | 0.0638 (9) | 0.0461 (7) | 0.0513 (8) | 0.0066 (6) | −0.0143 (7) | −0.0013 (6) |
O7 | 0.0552 (8) | 0.0592 (8) | 0.0586 (8) | 0.0159 (7) | 0.0110 (6) | 0.0147 (6) |
O8 | 0.0615 (8) | 0.0478 (7) | 0.0464 (7) | 0.0089 (6) | 0.0164 (6) | 0.0090 (6) |
C22 | 0.0549 (11) | 0.0468 (10) | 0.0413 (9) | 0.0068 (8) | −0.0039 (8) | −0.0043 (8) |
C24 | 0.0442 (9) | 0.0496 (10) | 0.0324 (8) | 0.0011 (8) | −0.0009 (7) | 0.0035 (7) |
C25 | 0.0482 (10) | 0.0399 (9) | 0.0376 (9) | −0.0024 (7) | −0.0003 (7) | −0.0010 (7) |
C26 | 0.0475 (10) | 0.0400 (9) | 0.0369 (9) | −0.0032 (7) | −0.0029 (7) | 0.0010 (7) |
C28 | 0.0692 (12) | 0.0421 (10) | 0.0418 (10) | 0.0010 (9) | 0.0009 (9) | 0.0011 (8) |
N21 | 0.0523 (9) | 0.0364 (8) | 0.0397 (8) | 0.0037 (7) | −0.0031 (6) | −0.0001 (6) |
N23 | 0.0607 (10) | 0.0471 (8) | 0.0372 (8) | 0.0077 (7) | −0.0028 (7) | 0.0012 (6) |
N27 | 0.0680 (10) | 0.0380 (7) | 0.0399 (8) | −0.0009 (7) | 0.0011 (7) | −0.0039 (6) |
N29 | 0.0644 (10) | 0.0452 (8) | 0.0346 (8) | 0.0036 (7) | −0.0005 (7) | 0.0069 (6) |
N30 | 0.0900 (13) | 0.0377 (8) | 0.0321 (8) | −0.0024 (8) | −0.0015 (8) | 0.0022 (7) |
C32 | 0.0772 (13) | 0.0439 (10) | 0.0305 (8) | 0.0043 (9) | −0.0008 (8) | −0.0003 (7) |
C34 | 0.0455 (9) | 0.0340 (8) | 0.0367 (8) | 0.0001 (7) | 0.0004 (7) | 0.0007 (7) |
C35 | 0.0440 (9) | 0.0340 (8) | 0.0318 (8) | 0.0005 (7) | 0.0014 (7) | −0.0011 (6) |
C36 | 0.0479 (9) | 0.0355 (8) | 0.0325 (8) | 0.0013 (7) | 0.0010 (7) | −0.0006 (7) |
C38 | 0.0580 (11) | 0.0331 (8) | 0.0422 (9) | 0.0025 (8) | 0.0016 (8) | −0.0068 (7) |
N31 | 0.0673 (10) | 0.0345 (7) | 0.0314 (7) | 0.0055 (7) | −0.0004 (7) | −0.0024 (6) |
N33 | 0.0746 (11) | 0.0385 (8) | 0.0349 (7) | 0.0034 (7) | −0.0013 (7) | 0.0026 (6) |
N37 | 0.0582 (9) | 0.0370 (7) | 0.0328 (7) | 0.0025 (6) | 0.0016 (6) | −0.0043 (6) |
N39 | 0.0566 (9) | 0.0299 (7) | 0.0426 (8) | 0.0015 (6) | 0.0007 (7) | 0.0015 (6) |
N40 | 0.0904 (13) | 0.0334 (8) | 0.0323 (8) | 0.0107 (8) | 0.0023 (8) | 0.0003 (6) |
O1W | 0.0657 (10) | 0.0528 (8) | 0.0574 (8) | 0.0024 (7) | 0.0051 (8) | 0.0179 (6) |
O2W | 0.097 (4) | 0.116 (4) | 0.097 (3) | −0.003 (3) | −0.021 (3) | −0.042 (3) |
Geometric parameters (Å, º) top
C1—O2 | 1.2488 (19) | C22—N21 | 1.347 (2) |
C1—O1 | 1.2608 (19) | C22—H22 | 0.9300 |
C1—C2 | 1.496 (2) | C24—N29 | 1.350 (2) |
C2—C3 | 1.392 (2) | C24—N23 | 1.362 (2) |
C2—C2i | 1.400 (3) | C24—C25 | 1.383 (2) |
C3—C4 | 1.381 (2) | C25—N27 | 1.376 (2) |
C3—H3 | 0.9300 | C25—C26 | 1.400 (2) |
C4—C4i | 1.377 (4) | C26—N30 | 1.314 (2) |
C4—H4 | 0.9300 | C26—N21 | 1.381 (2) |
C5—O3 | 1.2528 (19) | C28—N27 | 1.314 (2) |
C5—O4 | 1.2548 (19) | C28—N29 | 1.361 (2) |
C5—C6 | 1.499 (2) | C28—H28 | 0.9300 |
C6—C7 | 1.388 (2) | N21—H21 | 0.91 (2) |
C6—C6ii | 1.400 (3) | N29—H29 | 0.92 (2) |
C7—C8 | 1.383 (2) | N30—H301 | 0.90 (2) |
C7—H7 | 0.9300 | N30—H302 | 0.88 (2) |
C8—C8ii | 1.377 (4) | C32—N33 | 1.311 (2) |
C8—H8A | 0.9300 | C32—N31 | 1.342 (2) |
C9—O5 | 1.202 (2) | C32—H32 | 0.9300 |
C9—O6 | 1.317 (2) | C34—N33 | 1.357 (2) |
C9—C10 | 1.505 (2) | C34—N39 | 1.362 (2) |
C10—C11 | 1.388 (3) | C34—C35 | 1.379 (2) |
C10—C15 | 1.399 (2) | C35—N37 | 1.387 (2) |
C11—C12 | 1.378 (3) | C35—C36 | 1.409 (2) |
C11—H11 | 0.9300 | C36—N40 | 1.312 (2) |
C12—C13 | 1.377 (3) | C36—N31 | 1.358 (2) |
C12—H12 | 0.9300 | C38—N37 | 1.313 (2) |
C13—C14 | 1.376 (3) | C38—N39 | 1.353 (2) |
C13—H13 | 0.9300 | C38—H38 | 0.9300 |
C14—C15 | 1.392 (2) | N31—H31 | 0.930 (17) |
C14—H14 | 0.9300 | N39—H39 | 0.91 (2) |
C15—C16 | 1.485 (2) | N40—H401 | 0.87 (2) |
C16—O7 | 1.210 (2) | N40—H402 | 0.95 (2) |
C16—O8 | 1.316 (2) | O1W—H1W | 0.86 (3) |
O6—H6 | 0.93 (3) | O1W—H2W | 0.83 (4) |
O8—H8 | 0.88 (3) | O2W—H3W | 0.894 (11) |
C22—N23 | 1.302 (2) | O2W—H4W | 0.896 (10) |
| | | |
O2—C1—O1 | 123.13 (15) | N21—C22—H22 | 117.3 |
O2—C1—C2 | 119.83 (14) | N29—C24—N23 | 127.47 (15) |
O1—C1—C2 | 116.94 (14) | N29—C24—C25 | 105.30 (15) |
C3—C2—C2i | 119.25 (9) | N23—C24—C25 | 127.23 (16) |
C3—C2—C1 | 118.39 (14) | N27—C25—C24 | 111.32 (15) |
C2i—C2—C1 | 122.11 (8) | N27—C25—C26 | 130.81 (15) |
C4—C3—C2 | 120.68 (15) | C24—C25—C26 | 117.87 (15) |
C4—C3—H3 | 119.7 | N30—C26—N21 | 120.44 (16) |
C2—C3—H3 | 119.7 | N30—C26—C25 | 125.84 (16) |
C4i—C4—C3 | 120.07 (10) | N21—C26—C25 | 113.71 (14) |
C4i—C4—H4 | 120.0 | N27—C28—N29 | 113.70 (16) |
C3—C4—H4 | 120.0 | N27—C28—H28 | 123.1 |
O3—C5—O4 | 122.44 (15) | N29—C28—H28 | 123.1 |
O3—C5—C6 | 117.92 (13) | C22—N21—C26 | 123.55 (15) |
O4—C5—C6 | 119.54 (14) | C22—N21—H21 | 116.3 (13) |
C7—C6—C6ii | 119.46 (10) | C26—N21—H21 | 120.1 (13) |
C7—C6—C5 | 119.81 (14) | C22—N23—C24 | 112.22 (14) |
C6ii—C6—C5 | 120.36 (9) | C28—N27—C25 | 103.02 (14) |
C8—C7—C6 | 120.33 (16) | C24—N29—C28 | 106.67 (15) |
C8—C7—H7 | 119.8 | C24—N29—H29 | 122.8 (13) |
C6—C7—H7 | 119.8 | C28—N29—H29 | 130.5 (13) |
C8ii—C8—C7 | 120.16 (10) | C26—N30—H301 | 118.3 (14) |
C8ii—C8—H8A | 119.9 | C26—N30—H302 | 119.7 (13) |
C7—C8—H8A | 119.9 | H301—N30—H302 | 120.3 (19) |
O5—C9—O6 | 124.59 (18) | N33—C32—N31 | 126.29 (16) |
O5—C9—C10 | 123.29 (17) | N33—C32—H32 | 116.9 |
O6—C9—C10 | 111.96 (14) | N31—C32—H32 | 116.9 |
C11—C10—C15 | 119.17 (17) | N33—C34—N39 | 127.19 (15) |
C11—C10—C9 | 116.93 (15) | N33—C34—C35 | 126.78 (15) |
C15—C10—C9 | 123.89 (15) | N39—C34—C35 | 106.03 (14) |
C12—C11—C10 | 120.59 (17) | C34—C35—N37 | 110.17 (14) |
C12—C11—H11 | 119.7 | C34—C35—C36 | 117.93 (14) |
C10—C11—H11 | 119.7 | N37—C35—C36 | 131.87 (15) |
C13—C12—C11 | 120.43 (18) | N40—C36—N31 | 118.94 (15) |
C13—C12—H12 | 119.8 | N40—C36—C35 | 126.68 (15) |
C11—C12—H12 | 119.8 | N31—C36—C35 | 114.37 (14) |
C14—C13—C12 | 119.71 (18) | N37—C38—N39 | 113.76 (14) |
C14—C13—H13 | 120.1 | N37—C38—H38 | 123.1 |
C12—C13—H13 | 120.1 | N39—C38—H38 | 123.1 |
C13—C14—C15 | 120.78 (17) | C32—N31—C36 | 122.81 (14) |
C13—C14—H14 | 119.6 | C32—N31—H31 | 118.6 (16) |
C15—C14—H14 | 119.6 | C36—N31—H31 | 118.6 (16) |
C14—C15—C10 | 119.31 (16) | C32—N33—C34 | 111.80 (14) |
C14—C15—C16 | 120.66 (15) | C38—N37—C35 | 103.70 (13) |
C10—C15—C16 | 120.02 (15) | C38—N39—C34 | 106.35 (14) |
O7—C16—O8 | 123.33 (16) | C38—N39—H39 | 128.7 (13) |
O7—C16—C15 | 122.49 (15) | C34—N39—H39 | 124.8 (13) |
O8—C16—C15 | 114.17 (15) | C36—N40—H401 | 119.7 (14) |
C9—O6—H6 | 114.6 (17) | C36—N40—H402 | 121.9 (13) |
C16—O8—H8 | 107.1 (16) | H401—N40—H402 | 118.3 (19) |
N23—C22—N21 | 125.39 (16) | H1W—O1W—H2W | 107 (3) |
N23—C22—H22 | 117.3 | H3W—O2W—H4W | 113.3 (18) |
| | | |
O2—C1—C2—C3 | −44.4 (2) | N27—C25—C26—N30 | −0.7 (3) |
O1—C1—C2—C3 | 132.26 (17) | C24—C25—C26—N30 | 179.76 (19) |
O2—C1—C2—C2i | 141.4 (2) | N27—C25—C26—N21 | 178.77 (18) |
O1—C1—C2—C2i | −42.0 (3) | C24—C25—C26—N21 | −0.8 (2) |
C2i—C2—C3—C4 | 0.6 (3) | N23—C22—N21—C26 | −0.2 (3) |
C1—C2—C3—C4 | −173.87 (15) | N30—C26—N21—C22 | −179.36 (18) |
C2—C3—C4—C4i | −0.5 (3) | C25—C26—N21—C22 | 1.1 (3) |
O3—C5—C6—C7 | −128.20 (18) | N21—C22—N23—C24 | −1.0 (3) |
O4—C5—C6—C7 | 48.1 (2) | N29—C24—N23—C22 | −178.67 (18) |
O3—C5—C6—C6ii | 44.8 (3) | C25—C24—N23—C22 | 1.4 (3) |
O4—C5—C6—C6ii | −138.92 (19) | N29—C28—N27—C25 | 0.1 (2) |
C6ii—C6—C7—C8 | −2.6 (3) | C24—C25—N27—C28 | 0.0 (2) |
C5—C6—C7—C8 | 170.45 (15) | C26—C25—N27—C28 | −179.6 (2) |
C6—C7—C8—C8ii | −0.3 (3) | N23—C24—N29—C28 | −179.82 (19) |
O5—C9—C10—C11 | 85.2 (2) | C25—C24—N29—C28 | 0.2 (2) |
O6—C9—C10—C11 | −90.50 (19) | N27—C28—N29—C24 | −0.2 (2) |
O5—C9—C10—C15 | −96.1 (2) | N33—C34—C35—N37 | −178.81 (17) |
O6—C9—C10—C15 | 88.17 (19) | N39—C34—C35—N37 | 0.2 (2) |
C15—C10—C11—C12 | 0.4 (3) | N33—C34—C35—C36 | −0.7 (3) |
C9—C10—C11—C12 | 179.12 (17) | N39—C34—C35—C36 | 178.34 (15) |
C10—C11—C12—C13 | 0.0 (3) | C34—C35—C36—N40 | −177.81 (18) |
C11—C12—C13—C14 | −0.3 (3) | N37—C35—C36—N40 | −0.2 (3) |
C12—C13—C14—C15 | 0.2 (3) | C34—C35—C36—N31 | 1.5 (2) |
C13—C14—C15—C10 | 0.2 (3) | N37—C35—C36—N31 | 179.13 (18) |
C13—C14—C15—C16 | 179.28 (16) | N33—C32—N31—C36 | −0.1 (3) |
C11—C10—C15—C14 | −0.5 (2) | N40—C36—N31—C32 | 178.19 (19) |
C9—C10—C15—C14 | −179.14 (15) | C35—C36—N31—C32 | −1.2 (3) |
C11—C10—C15—C16 | −179.55 (15) | N31—C32—N33—C34 | 1.0 (3) |
C9—C10—C15—C16 | 1.8 (2) | N39—C34—N33—C32 | −179.41 (18) |
C14—C15—C16—O7 | −159.69 (17) | C35—C34—N33—C32 | −0.6 (3) |
C10—C15—C16—O7 | 19.4 (2) | N39—C38—N37—C35 | 0.3 (2) |
C14—C15—C16—O8 | 19.6 (2) | C34—C35—N37—C38 | −0.3 (2) |
C10—C15—C16—O8 | −161.38 (15) | C36—C35—N37—C38 | −178.09 (19) |
N29—C24—C25—N27 | −0.1 (2) | N37—C38—N39—C34 | −0.2 (2) |
N23—C24—C25—N27 | 179.90 (17) | N33—C34—N39—C38 | 179.01 (18) |
N29—C24—C25—C26 | 179.53 (16) | C35—C34—N39—C38 | −0.03 (19) |
N23—C24—C25—C26 | −0.5 (3) | | |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O4 | 0.91 (2) | 1.84 (2) | 2.7408 (18) | 171 (2) |
N29—H29···N37 | 0.92 (2) | 1.97 (2) | 2.888 (2) | 171.1 (19) |
N30—H301···O3 | 0.90 (2) | 1.86 (2) | 2.757 (2) | 172 (2) |
N30—H302···N33iii | 0.88 (2) | 2.11 (2) | 2.971 (2) | 168.6 (18) |
N31—H31···O1 | 0.93 (2) | 1.67 (2) | 2.5930 (19) | 174 (2) |
N39—H39···O1W | 0.91 (2) | 1.86 (2) | 2.766 (2) | 174 (2) |
N40—H401···O2 | 0.87 (2) | 2.01 (2) | 2.851 (2) | 164 (2) |
N40—H402···N23 | 0.95 (2) | 2.00 (2) | 2.935 (2) | 167.5 (19) |
O6—H6···O2 | 0.93 (3) | 1.70 (3) | 2.6356 (18) | 177 (3) |
O8—H8···O4 | 0.88 (3) | 1.74 (3) | 2.6207 (18) | 175 (2) |
O1W—H1W···O3iv | 0.86 (3) | 1.94 (3) | 2.769 (2) | 162 (3) |
O1W—H2W···O3v | 0.83 (4) | 2.24 (4) | 3.060 (2) | 172 (4) |
O2W—H3W···O1vi | 0.89 (1) | 2.00 (5) | 2.786 (4) | 146 (7) |
O2W—H4W···O1 | 0.90 (1) | 2.30 (7) | 3.074 (6) | 145 (10) |
Symmetry codes: (iii) x, −y+1, z−1/2; (iv) x, −y+1, z+1/2; (v) −x+2, −y+1, −z+1; (vi) −x+2, y, −z+3/2. |