organic compounds
of [propane-1,3-diylbis(piperidine-4,1-diyl)]bis[(pyridin-4-yl)methanone]–4,4′-oxydibenzoic acid (1/1)
aHeritage High School, Rogers, AR 72756, USA, and bLyman Briggs College, Department of Chemistry, E-30 Holmes Hall, 919 East Shaw Lane, Michigan State University, East Lansing, MI 48825, USA
*Correspondence e-mail: laduca@msu.edu
In the title 25H32N4O2·C14H10O5, molecules are connected into supramolecular chains aligned along [102] by O—H⋯N hydrogen bonding. These aggregate into supramolecular layers oriented parallel to (20-1) by C—H⋯O interactions. These layers then stack in an ABAB pattern along the c crystal direction to give the full three-dimensional The central chain in the dipyridylamide has an anti–anti conformation. The dihedral angle between the aromatic ring planes is 29.96 (3)°. Disorder is noted in some of the residues in the structure and this is manifested in two coplanar dispositions of one statistically disordered carboxylic acid group.
CKeywords: crystal structure; co-crystal; hydrogen bonding; piperazine-1,4-diylbis(pyridin-4-ylmethanone); 4,4′-oxydibenzoic acid.
CCDC reference: 1018294
1. Related literature
For the preparation of piperazine-1,4-diylbis(pyridin-4-ylmethanone), see: Hou et al. (2003). For the preparation of divalent metal 4,4′-oxydibenzoate coordination polymers, see: Yang et al. (2009).
2. Experimental
2.1. Crystal data
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2.1.3. Refinement
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Data collection: APEX2 (Bruker, 2012); cell APEX2; data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Supporting information
CCDC reference: 1018294
10.1107/S160053681401811X/tk5333sup1.cif
contains datablocks I, pub. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681401811X/tk5333Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681401811X/tk5333Isup3.cml
Some divalent metal 4,4'-oxydibenzoate (oba) coordination polymers show intriguing self-penetrated topologies (Yang et al., 2009). We therefore attempted to expand the scope of these materials by using the very-long spanning dipyridyl ligand propane-1,3-diylbis(piperidine-4,1-diyl))bis(pyridin-4-ylmethanone (ppbp). The title compound was obtained as colorless crystals through the hydrothermal reaction of zinc nitrate, H2oba, and ppbp.
The
of the title compound contains a full H2oba molecule with one of its carboxylic acid termini disordered in a 50/50 ratio, and a full ppbp molecule (Fig. 1). The H2oba and ppbp molecules are connected into supramolecular chains (Fig. 2) aligned along [1 0 2] by O—H···N hydrogen bonding (Table 1) between unprotonated ppbp pyridyl N atoms and protonated H2oba carboxylate O atoms.These chains aggregate into supramolecular layers oriented parallel to the (2 0 1) crystal planes by C—H···O interactions between ppbp pyridyl C atoms and unprotonated H2oba carboxylate O atoms (C···O distance = 3.114 (8) Å). These layers then stack in an ABAB pattern along the c crystal direction to give the full three-dimensional of the title (Fig. 3). The stacking is mediated by C—H···O interactions between ppbp trimethylene linker C atoms and ppbp amide O atoms (C···O distance = 3.453 (7) Å) and also by C—H···O interactions between H2oba aromatic C atoms and unprotonated H2oba carboxylate O atoms (C···O distance = 3.555 (7) Å).
Zinc(II) nitrate hexahydrate and 4,4'-oxydibenzoic acid (H2oba) were obtained commercially. Propane-1,3-diylbis(piperidine-4,1-diyl))bis(pyridin-4-ylmethanone (ppbp) was prepared via modification of a published procedure for the synthesis of piperazine-1,4-diylbis(pyridin-4-ylmethanone) (Hou et al., 2003), using trimethylenepiperidine instead of piperazine as the amine precursor. A mixture of zinc(II) nitrate hexahydrate (110 mg, 0.37 mmol), H2oba (96 mg, 0.37 mmol), ppbp (115 mg, 0.37 mmol), 1.0 mL of a 1.0 M NaOH solution, and 10.0 g water (550 mmol) was placed into a 23 ml Teflon-lined Parr acid digestion bomb, which was then heated under autogenous pressure at 393 K for 72 h. Colorless plates of the title compound were obtained along with some amorphous white powder.
Data collection: APEX2 (Bruker, 2012); cell
APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).Fig. 1. The formula unit of the title compound, showing 50% probability ellipsoids and atom numbering scheme. Most hydrogen atom positions are shown as grey sticks. Color codes: Red O, light blue N, black C, pink H. Only one of the disordered carboxylic acid groups is shown. | |
Fig. 2. Layer pattern within the title compound constructed from supramolecular chains connected by O—H···N hydrogen bonding. | |
Fig. 3. Stacking of supramolecular layers within the title compound. |
C25H32N4O2·C14H10O5 | F(000) = 1440 |
Mr = 678.77 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.032 (4) Å | Cell parameters from 7245 reflections |
b = 12.605 (4) Å | θ = 2.4–21.9° |
c = 17.259 (5) Å | µ = 0.09 mm−1 |
β = 99.033 (7)° | T = 173 K |
V = 3444.4 (16) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.17 × 0.15 mm |
Bruker APEXII CCD diffractometer | 6304 independent reflections |
Radiation source: fine-focus sealed tube | 3501 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
ϕ and ω scans | θmax = 25.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS2012; Bruker, 2012) | h = −19→19 |
Tmin = 0.715, Tmax = 0.745 | k = −15→15 |
55666 measured reflections | l = −20→20 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0533P)2 + 1.9615P] where P = (Fo2 + 2Fc2)/3 |
6304 reflections | (Δ/σ)max = 0.001 |
457 parameters | Δρmax = 0.50 e Å−3 |
2 restraints | Δρmin = −0.54 e Å−3 |
C25H32N4O2·C14H10O5 | V = 3444.4 (16) Å3 |
Mr = 678.77 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.032 (4) Å | µ = 0.09 mm−1 |
b = 12.605 (4) Å | T = 173 K |
c = 17.259 (5) Å | 0.22 × 0.17 × 0.15 mm |
β = 99.033 (7)° |
Bruker APEXII CCD diffractometer | 6304 independent reflections |
Absorption correction: multi-scan (SADABS2012; Bruker, 2012) | 3501 reflections with I > 2σ(I) |
Tmin = 0.715, Tmax = 0.745 | Rint = 0.095 |
55666 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 2 restraints |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.50 e Å−3 |
6304 reflections | Δρmin = −0.54 e Å−3 |
457 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.64279 (13) | 1.41437 (15) | 1.60440 (11) | 0.0473 (5) | |
O2 | 0.34348 (13) | 1.40624 (15) | 0.85532 (11) | 0.0458 (5) | |
O3 | −0.00461 (12) | 0.80814 (14) | 0.23098 (10) | 0.0391 (5) | |
O4 | −0.16756 (13) | 1.08325 (16) | −0.06306 (10) | 0.0438 (5) | |
H4A | −0.1820 | 1.1041 | −0.1095 | 0.066* | |
O5 | −0.11387 (14) | 0.94796 (16) | −0.12257 (11) | 0.0492 (6) | |
O6 | 0.1453 (4) | 1.1087 (4) | 0.5139 (3) | 0.0499 (7) | 0.50 |
O6A | 0.1506 (4) | 1.0685 (5) | 0.5354 (3) | 0.0499 (7) | 0.50 |
O7 | 0.1450 (4) | 0.9583 (4) | 0.5765 (4) | 0.0499 (7) | 0.50 |
O7A | 0.1286 (4) | 0.9109 (4) | 0.5858 (3) | 0.0499 (7) | 0.50 |
N1 | 0.78276 (15) | 1.15847 (19) | 1.79278 (13) | 0.0399 (6) | |
N2 | 0.65133 (14) | 1.28497 (17) | 1.51423 (12) | 0.0338 (5) | |
N3 | 0.32687 (14) | 1.28701 (17) | 0.95014 (12) | 0.0349 (6) | |
N4 | 0.2102 (2) | 1.1243 (3) | 0.68184 (17) | 0.0755 (11) | |
C1 | 0.80512 (17) | 1.2576 (2) | 1.77677 (15) | 0.0379 (7) | |
H1 | 0.8461 | 1.2932 | 1.8134 | 0.045* | |
C2 | 0.77083 (16) | 1.3097 (2) | 1.70900 (15) | 0.0344 (7) | |
H2 | 0.7881 | 1.3800 | 1.6997 | 0.041* | |
C3 | 0.71111 (16) | 1.2594 (2) | 1.65447 (14) | 0.0308 (6) | |
C4 | 0.68972 (18) | 1.1559 (2) | 1.67015 (15) | 0.0357 (7) | |
H4 | 0.6502 | 1.1177 | 1.6338 | 0.043* | |
C5 | 0.72678 (19) | 1.1091 (2) | 1.73961 (16) | 0.0417 (7) | |
H5 | 0.7116 | 1.0383 | 1.7499 | 0.050* | |
C6 | 0.66657 (17) | 1.3255 (2) | 1.58778 (15) | 0.0335 (7) | |
C7 | 0.60681 (18) | 1.3526 (2) | 1.45183 (15) | 0.0407 (7) | |
H7A | 0.6486 | 1.3910 | 1.4258 | 0.049* | |
H7B | 0.5727 | 1.4058 | 1.4751 | 0.049* | |
C8 | 0.54927 (17) | 1.2874 (2) | 1.39107 (15) | 0.0356 (7) | |
H8A | 0.5025 | 1.2578 | 1.4156 | 0.043* | |
H8B | 0.5243 | 1.3345 | 1.3477 | 0.043* | |
C9 | 0.59577 (17) | 1.1970 (2) | 1.35774 (15) | 0.0327 (6) | |
H9 | 0.6401 | 1.2291 | 1.3303 | 0.039* | |
C10 | 0.64064 (17) | 1.1307 (2) | 1.42608 (15) | 0.0357 (7) | |
H10A | 0.5979 | 1.0958 | 1.4531 | 0.043* | |
H10B | 0.6742 | 1.0745 | 1.4054 | 0.043* | |
C11 | 0.69871 (17) | 1.1977 (2) | 1.48491 (15) | 0.0366 (7) | |
H11A | 0.7243 | 1.1527 | 1.5294 | 0.044* | |
H11B | 0.7449 | 1.2272 | 1.4595 | 0.044* | |
C12 | 0.53838 (17) | 1.1296 (2) | 1.29791 (15) | 0.0368 (7) | |
H12A | 0.5730 | 1.0759 | 1.2758 | 0.044* | |
H12B | 0.4972 | 1.0915 | 1.3249 | 0.044* | |
C13 | 0.49058 (17) | 1.1954 (2) | 1.23118 (15) | 0.0367 (7) | |
H13A | 0.4503 | 1.2421 | 1.2529 | 0.044* | |
H13B | 0.5315 | 1.2416 | 1.2098 | 0.044* | |
C14 | 0.44192 (17) | 1.1314 (2) | 1.16393 (15) | 0.0373 (7) | |
H14A | 0.4081 | 1.0765 | 1.1859 | 0.045* | |
H14B | 0.4827 | 1.0946 | 1.1357 | 0.045* | |
C15 | 0.37015 (19) | 1.3554 (2) | 1.01205 (15) | 0.0418 (7) | |
H15A | 0.3279 | 1.3924 | 1.0384 | 0.050* | |
H15B | 0.4033 | 1.4096 | 0.9887 | 0.050* | |
C16 | 0.42860 (18) | 1.2909 (2) | 1.07196 (15) | 0.0374 (7) | |
H16A | 0.4536 | 1.3381 | 1.1153 | 0.045* | |
H16B | 0.4752 | 1.2621 | 1.0469 | 0.045* | |
C17 | 0.38314 (16) | 1.1994 (2) | 1.10569 (14) | 0.0319 (6) | |
H17 | 0.3397 | 1.2309 | 1.1346 | 0.038* | |
C18 | 0.33638 (17) | 1.1332 (2) | 1.03817 (14) | 0.0334 (6) | |
H18A | 0.3781 | 1.0969 | 1.0107 | 0.040* | |
H18B | 0.3024 | 1.0781 | 1.0597 | 0.040* | |
C19 | 0.27875 (17) | 1.2011 (2) | 0.98003 (15) | 0.0341 (7) | |
H19A | 0.2520 | 1.1565 | 0.9358 | 0.041* | |
H19B | 0.2334 | 1.2317 | 1.0060 | 0.041* | |
C20 | 0.31728 (16) | 1.3201 (2) | 0.87516 (15) | 0.0335 (7) | |
C21 | 0.1847 (2) | 1.2234 (4) | 0.69088 (19) | 0.0684 (12) | |
H21 | 0.1423 | 1.2519 | 0.6518 | 0.082* | |
C22 | 0.21603 (18) | 1.2868 (3) | 0.75303 (16) | 0.0454 (8) | |
H22 | 0.1962 | 1.3574 | 0.7561 | 0.054* | |
C23 | 0.27722 (17) | 1.2464 (2) | 0.81168 (15) | 0.0340 (7) | |
C24 | 0.30416 (18) | 1.1427 (2) | 0.80403 (16) | 0.0409 (7) | |
H24 | 0.3454 | 1.1116 | 0.8430 | 0.049* | |
C25 | 0.2693 (2) | 1.0857 (3) | 0.7380 (2) | 0.0593 (10) | |
H25 | 0.2887 | 1.0153 | 0.7324 | 0.071* | |
C26 | −0.12708 (16) | 0.9924 (2) | −0.06313 (16) | 0.0336 (7) | |
C27 | −0.09764 (16) | 0.9483 (2) | 0.01669 (14) | 0.0294 (6) | |
C28 | −0.11189 (17) | 0.9983 (2) | 0.08546 (15) | 0.0353 (7) | |
H28 | −0.1424 | 1.0631 | 0.0826 | 0.042* | |
C29 | −0.08188 (17) | 0.9540 (2) | 0.15812 (15) | 0.0373 (7) | |
H29 | −0.0927 | 0.9875 | 0.2048 | 0.045* | |
C30 | −0.03600 (16) | 0.8606 (2) | 0.16198 (14) | 0.0315 (6) | |
C31 | −0.02433 (17) | 0.8077 (2) | 0.09456 (15) | 0.0353 (7) | |
H31 | 0.0045 | 0.7416 | 0.0976 | 0.042* | |
C32 | −0.05520 (17) | 0.8522 (2) | 0.02257 (15) | 0.0347 (7) | |
H32 | −0.0471 | 0.8160 | −0.0240 | 0.042* | |
C33 | 0.1311 (5) | 1.0135 (7) | 0.5137 (4) | 0.0499 (7) | 0.50 |
C33A | 0.1258 (5) | 0.9681 (6) | 0.5283 (5) | 0.0499 (7) | 0.50 |
C34 | 0.09603 (18) | 0.9448 (3) | 0.44368 (16) | 0.0453 (8) | |
C35 | 0.09003 (18) | 1.0061 (2) | 0.37619 (18) | 0.0467 (8) | |
H35 | 0.1085 | 1.0778 | 0.3799 | 0.056* | |
C36 | 0.05732 (18) | 0.9641 (2) | 0.30305 (16) | 0.0415 (7) | |
H36 | 0.0546 | 1.0058 | 0.2569 | 0.050* | |
C37 | 0.02892 (16) | 0.8607 (2) | 0.29897 (14) | 0.0314 (6) | |
C38 | 0.03782 (17) | 0.7979 (2) | 0.36559 (15) | 0.0402 (7) | |
H38 | 0.0206 | 0.7258 | 0.3618 | 0.048* | |
C39 | 0.07165 (18) | 0.8400 (3) | 0.43725 (16) | 0.0477 (8) | |
H39 | 0.0782 | 0.7964 | 0.4827 | 0.057* | |
H7 | 0.167 (4) | 1.000 (5) | 0.614 (3) | 0.10 (3)* | 0.50 |
H6A | 0.171 (3) | 1.088 (5) | 0.5825 (19) | 0.06 (2)* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0639 (14) | 0.0333 (12) | 0.0412 (12) | 0.0047 (10) | −0.0024 (10) | −0.0037 (9) |
O2 | 0.0561 (14) | 0.0353 (12) | 0.0431 (12) | −0.0068 (10) | −0.0015 (10) | 0.0100 (10) |
O3 | 0.0512 (12) | 0.0397 (11) | 0.0240 (10) | −0.0002 (10) | −0.0021 (9) | 0.0004 (9) |
O4 | 0.0481 (13) | 0.0512 (13) | 0.0307 (11) | 0.0085 (11) | 0.0016 (10) | 0.0056 (10) |
O5 | 0.0685 (15) | 0.0533 (13) | 0.0243 (11) | 0.0073 (11) | 0.0031 (10) | −0.0018 (10) |
O6 | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
O6A | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
O7 | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
O7A | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
N1 | 0.0456 (15) | 0.0435 (16) | 0.0294 (13) | 0.0116 (13) | 0.0019 (11) | −0.0008 (11) |
N2 | 0.0411 (14) | 0.0305 (13) | 0.0271 (12) | 0.0045 (11) | −0.0032 (10) | 0.0015 (10) |
N3 | 0.0422 (14) | 0.0308 (13) | 0.0290 (13) | −0.0058 (11) | −0.0031 (10) | −0.0008 (10) |
N4 | 0.051 (2) | 0.135 (3) | 0.0429 (18) | −0.039 (2) | 0.0151 (15) | −0.038 (2) |
C1 | 0.0354 (16) | 0.0471 (19) | 0.0297 (16) | 0.0010 (14) | 0.0009 (12) | −0.0081 (14) |
C2 | 0.0351 (16) | 0.0354 (16) | 0.0322 (15) | −0.0047 (13) | 0.0032 (13) | −0.0017 (13) |
C3 | 0.0323 (15) | 0.0337 (16) | 0.0258 (14) | 0.0008 (12) | 0.0026 (12) | −0.0002 (12) |
C4 | 0.0449 (17) | 0.0327 (16) | 0.0280 (15) | 0.0005 (13) | 0.0013 (13) | −0.0029 (12) |
C5 | 0.055 (2) | 0.0330 (16) | 0.0366 (17) | 0.0022 (15) | 0.0065 (15) | −0.0022 (14) |
C6 | 0.0360 (16) | 0.0305 (16) | 0.0323 (16) | −0.0059 (13) | −0.0004 (12) | −0.0009 (13) |
C7 | 0.0519 (19) | 0.0337 (17) | 0.0328 (16) | 0.0034 (14) | −0.0054 (14) | 0.0058 (13) |
C8 | 0.0419 (17) | 0.0342 (16) | 0.0285 (15) | 0.0043 (13) | −0.0008 (12) | 0.0036 (12) |
C9 | 0.0338 (15) | 0.0363 (16) | 0.0274 (14) | −0.0008 (13) | 0.0031 (12) | 0.0031 (12) |
C10 | 0.0402 (17) | 0.0312 (16) | 0.0344 (16) | 0.0061 (13) | 0.0013 (13) | −0.0006 (13) |
C11 | 0.0352 (16) | 0.0408 (17) | 0.0328 (16) | 0.0074 (13) | 0.0017 (13) | 0.0024 (13) |
C12 | 0.0387 (16) | 0.0389 (17) | 0.0312 (15) | 0.0025 (14) | 0.0005 (13) | −0.0017 (13) |
C13 | 0.0356 (16) | 0.0419 (17) | 0.0315 (15) | 0.0003 (14) | 0.0018 (12) | 0.0008 (14) |
C14 | 0.0383 (17) | 0.0400 (17) | 0.0324 (16) | −0.0014 (14) | 0.0019 (13) | −0.0021 (13) |
C15 | 0.0560 (19) | 0.0340 (17) | 0.0322 (16) | −0.0095 (15) | −0.0034 (14) | −0.0043 (13) |
C16 | 0.0439 (17) | 0.0381 (17) | 0.0274 (15) | −0.0083 (14) | −0.0025 (13) | −0.0074 (13) |
C17 | 0.0320 (15) | 0.0364 (16) | 0.0269 (14) | 0.0002 (13) | 0.0031 (12) | −0.0014 (12) |
C18 | 0.0365 (16) | 0.0329 (16) | 0.0298 (15) | −0.0062 (13) | 0.0025 (12) | 0.0007 (12) |
C19 | 0.0371 (16) | 0.0332 (16) | 0.0311 (15) | −0.0088 (13) | 0.0024 (12) | −0.0001 (12) |
C20 | 0.0309 (15) | 0.0336 (17) | 0.0344 (16) | 0.0029 (13) | 0.0000 (12) | 0.0019 (13) |
C21 | 0.039 (2) | 0.136 (4) | 0.0283 (18) | −0.018 (2) | 0.0021 (15) | −0.002 (2) |
C22 | 0.0365 (17) | 0.069 (2) | 0.0292 (16) | −0.0046 (16) | −0.0007 (13) | 0.0085 (15) |
C23 | 0.0322 (16) | 0.0411 (17) | 0.0281 (15) | −0.0035 (13) | 0.0032 (12) | 0.0038 (13) |
C24 | 0.0440 (18) | 0.0410 (18) | 0.0380 (17) | −0.0094 (15) | 0.0075 (14) | −0.0028 (14) |
C25 | 0.057 (2) | 0.064 (2) | 0.062 (2) | −0.0238 (19) | 0.0262 (19) | −0.0260 (19) |
C26 | 0.0289 (15) | 0.0369 (17) | 0.0345 (16) | −0.0010 (13) | 0.0033 (12) | 0.0022 (14) |
C27 | 0.0255 (14) | 0.0351 (16) | 0.0268 (14) | −0.0057 (12) | 0.0014 (11) | −0.0007 (12) |
C28 | 0.0358 (16) | 0.0357 (16) | 0.0335 (16) | 0.0017 (13) | 0.0027 (13) | −0.0019 (13) |
C29 | 0.0415 (17) | 0.0444 (18) | 0.0258 (15) | 0.0044 (14) | 0.0048 (13) | −0.0038 (13) |
C30 | 0.0322 (15) | 0.0369 (16) | 0.0239 (14) | −0.0027 (13) | −0.0005 (12) | 0.0024 (13) |
C31 | 0.0374 (16) | 0.0354 (16) | 0.0317 (16) | 0.0016 (13) | 0.0016 (13) | −0.0038 (13) |
C32 | 0.0386 (16) | 0.0401 (17) | 0.0245 (14) | 0.0010 (14) | 0.0019 (12) | −0.0052 (13) |
C33 | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
C33A | 0.0616 (13) | 0.051 (3) | 0.0325 (16) | −0.0039 (17) | −0.0055 (12) | −0.0009 (16) |
C34 | 0.0309 (17) | 0.073 (2) | 0.0297 (16) | 0.0058 (16) | −0.0011 (13) | −0.0118 (16) |
C35 | 0.0406 (18) | 0.0453 (19) | 0.051 (2) | −0.0009 (15) | −0.0022 (15) | −0.0143 (16) |
C36 | 0.0456 (18) | 0.0470 (19) | 0.0303 (16) | −0.0005 (15) | 0.0012 (13) | 0.0051 (14) |
C37 | 0.0320 (15) | 0.0391 (17) | 0.0230 (14) | 0.0025 (13) | 0.0044 (11) | −0.0009 (13) |
C38 | 0.0381 (17) | 0.0485 (19) | 0.0321 (17) | −0.0032 (14) | −0.0001 (13) | 0.0084 (14) |
C39 | 0.0382 (17) | 0.075 (2) | 0.0278 (16) | −0.0014 (17) | −0.0005 (13) | 0.0087 (16) |
O1—C6 | 1.232 (3) | C13—H13A | 0.9900 |
O2—C20 | 1.232 (3) | C13—H13B | 0.9900 |
O3—C30 | 1.386 (3) | C13—C14 | 1.524 (4) |
O3—C37 | 1.381 (3) | C14—H14A | 0.9900 |
O4—H4A | 0.8400 | C14—H14B | 0.9900 |
O4—C26 | 1.316 (3) | C14—C17 | 1.528 (4) |
O5—C26 | 1.217 (3) | C15—H15A | 0.9900 |
O6—C33 | 1.222 (9) | C15—H15B | 0.9900 |
O6—H6A | 1.22 (4) | C15—C16 | 1.517 (4) |
O6A—C33A | 1.327 (8) | C16—H16A | 0.9900 |
O6A—H6A | 0.86 (2) | C16—H16B | 0.9900 |
O7—C33 | 1.278 (8) | C16—C17 | 1.528 (4) |
O7—H7 | 0.86 (2) | C17—H17 | 1.0000 |
O7A—C33A | 1.221 (9) | C17—C18 | 1.530 (3) |
O7A—H7 | 1.34 (4) | C18—H18A | 0.9900 |
N1—C1 | 1.340 (4) | C18—H18B | 0.9900 |
N1—C5 | 1.332 (3) | C18—C19 | 1.517 (3) |
N2—C6 | 1.354 (3) | C19—H19A | 0.9900 |
N2—C7 | 1.468 (3) | C19—H19B | 0.9900 |
N2—C11 | 1.471 (3) | C20—C23 | 1.501 (4) |
N3—C15 | 1.460 (3) | C21—H21 | 0.9500 |
N3—C19 | 1.470 (3) | C21—C22 | 1.368 (5) |
N3—C20 | 1.345 (3) | C22—H22 | 0.9500 |
N4—C21 | 1.331 (5) | C22—C23 | 1.391 (4) |
N4—C25 | 1.337 (5) | C23—C24 | 1.390 (4) |
C1—H1 | 0.9500 | C24—H24 | 0.9500 |
C1—C2 | 1.378 (4) | C24—C25 | 1.388 (4) |
C2—H2 | 0.9500 | C25—H25 | 0.9500 |
C2—C3 | 1.386 (4) | C26—C27 | 1.492 (4) |
C3—C4 | 1.386 (4) | C27—C28 | 1.394 (3) |
C3—C6 | 1.507 (4) | C27—C32 | 1.386 (4) |
C4—H4 | 0.9500 | C28—H28 | 0.9500 |
C4—C5 | 1.384 (4) | C28—C29 | 1.388 (4) |
C5—H5 | 0.9500 | C29—H29 | 0.9500 |
C7—H7A | 0.9900 | C29—C30 | 1.384 (4) |
C7—H7B | 0.9900 | C30—C31 | 1.379 (3) |
C7—C8 | 1.524 (4) | C31—H31 | 0.9500 |
C8—H8A | 0.9900 | C31—C32 | 1.382 (4) |
C8—H8B | 0.9900 | C32—H32 | 0.9500 |
C8—C9 | 1.523 (4) | C33—C34 | 1.520 (9) |
C9—H9 | 1.0000 | C33A—C34 | 1.493 (9) |
C9—C10 | 1.530 (3) | C34—C35 | 1.388 (4) |
C9—C12 | 1.528 (4) | C34—C39 | 1.377 (4) |
C10—H10A | 0.9900 | C35—H35 | 0.9500 |
C10—H10B | 0.9900 | C35—C36 | 1.393 (4) |
C10—C11 | 1.521 (4) | C36—H36 | 0.9500 |
C11—H11A | 0.9900 | C36—C37 | 1.379 (4) |
C11—H11B | 0.9900 | C37—C38 | 1.385 (4) |
C12—H12A | 0.9900 | C38—H38 | 0.9500 |
C12—H12B | 0.9900 | C38—C39 | 1.377 (4) |
C12—C13 | 1.525 (4) | C39—H39 | 0.9500 |
C37—O3—C30 | 122.8 (2) | C17—C16—H16B | 109.1 |
C26—O4—H4A | 109.5 | C14—C17—C16 | 113.1 (2) |
C33—O6—H6A | 80 (3) | C14—C17—H17 | 107.5 |
C33A—O6A—H6A | 115 (5) | C14—C17—C18 | 111.9 (2) |
C33—O7—H7 | 107 (6) | C16—C17—H17 | 107.5 |
C33A—O7A—H7 | 76 (3) | C16—C17—C18 | 109.1 (2) |
C5—N1—C1 | 117.8 (2) | C18—C17—H17 | 107.5 |
C6—N2—C7 | 117.7 (2) | C17—C18—H18A | 109.3 |
C6—N2—C11 | 125.3 (2) | C17—C18—H18B | 109.3 |
C7—N2—C11 | 113.5 (2) | H18A—C18—H18B | 107.9 |
C15—N3—C19 | 113.2 (2) | C19—C18—C17 | 111.8 (2) |
C20—N3—C15 | 119.3 (2) | C19—C18—H18A | 109.3 |
C20—N3—C19 | 125.4 (2) | C19—C18—H18B | 109.3 |
C21—N4—C25 | 116.9 (3) | N3—C19—C18 | 110.4 (2) |
N1—C1—H1 | 118.8 | N3—C19—H19A | 109.6 |
N1—C1—C2 | 122.3 (3) | N3—C19—H19B | 109.6 |
C2—C1—H1 | 118.8 | C18—C19—H19A | 109.6 |
C1—C2—H2 | 120.0 | C18—C19—H19B | 109.6 |
C1—C2—C3 | 120.0 (3) | H19A—C19—H19B | 108.1 |
C3—C2—H2 | 120.0 | O2—C20—N3 | 123.3 (2) |
C2—C3—C6 | 117.4 (2) | O2—C20—C23 | 117.9 (2) |
C4—C3—C2 | 117.6 (2) | N3—C20—C23 | 118.8 (2) |
C4—C3—C6 | 124.5 (2) | N4—C21—H21 | 118.0 |
C3—C4—H4 | 120.5 | N4—C21—C22 | 123.9 (4) |
C5—C4—C3 | 119.0 (3) | C22—C21—H21 | 118.0 |
C5—C4—H4 | 120.5 | C21—C22—H22 | 120.4 |
N1—C5—C4 | 123.3 (3) | C21—C22—C23 | 119.2 (3) |
N1—C5—H5 | 118.3 | C23—C22—H22 | 120.4 |
C4—C5—H5 | 118.3 | C22—C23—C20 | 118.5 (3) |
O1—C6—N2 | 123.0 (2) | C24—C23—C20 | 123.2 (2) |
O1—C6—C3 | 116.9 (2) | C24—C23—C22 | 118.0 (3) |
N2—C6—C3 | 120.1 (2) | C23—C24—H24 | 120.9 |
N2—C7—H7A | 109.4 | C25—C24—C23 | 118.3 (3) |
N2—C7—H7B | 109.4 | C25—C24—H24 | 120.9 |
N2—C7—C8 | 111.4 (2) | N4—C25—C24 | 123.7 (3) |
H7A—C7—H7B | 108.0 | N4—C25—H25 | 118.1 |
C8—C7—H7A | 109.4 | C24—C25—H25 | 118.1 |
C8—C7—H7B | 109.4 | O4—C26—C27 | 114.1 (2) |
C7—C8—H8A | 109.1 | O5—C26—O4 | 123.6 (3) |
C7—C8—H8B | 109.1 | O5—C26—C27 | 122.3 (3) |
H8A—C8—H8B | 107.8 | C28—C27—C26 | 123.2 (2) |
C9—C8—C7 | 112.6 (2) | C32—C27—C26 | 118.3 (2) |
C9—C8—H8A | 109.1 | C32—C27—C28 | 118.5 (2) |
C9—C8—H8B | 109.1 | C27—C28—H28 | 119.7 |
C8—C9—H9 | 107.6 | C29—C28—C27 | 120.5 (3) |
C8—C9—C10 | 108.4 (2) | C29—C28—H28 | 119.7 |
C8—C9—C12 | 113.1 (2) | C28—C29—H29 | 120.3 |
C10—C9—H9 | 107.6 | C30—C29—C28 | 119.4 (2) |
C12—C9—H9 | 107.6 | C30—C29—H29 | 120.3 |
C12—C9—C10 | 112.2 (2) | C29—C30—O3 | 124.5 (2) |
C9—C10—H10A | 109.2 | C31—C30—O3 | 114.5 (2) |
C9—C10—H10B | 109.2 | C31—C30—C29 | 120.8 (2) |
H10A—C10—H10B | 107.9 | C30—C31—H31 | 120.5 |
C11—C10—C9 | 112.1 (2) | C30—C31—C32 | 119.1 (3) |
C11—C10—H10A | 109.2 | C32—C31—H31 | 120.5 |
C11—C10—H10B | 109.2 | C27—C32—H32 | 119.2 |
N2—C11—C10 | 110.5 (2) | C31—C32—C27 | 121.5 (2) |
N2—C11—H11A | 109.6 | C31—C32—H32 | 119.2 |
N2—C11—H11B | 109.6 | O6—C33—O7 | 121.6 (8) |
C10—C11—H11A | 109.6 | O6—C33—C34 | 127.4 (6) |
C10—C11—H11B | 109.6 | O6—C33—H6A | 50 (2) |
H11A—C11—H11B | 108.1 | O7—C33—C34 | 111.0 (7) |
C9—C12—H12A | 109.1 | O7—C33—H6A | 72 (2) |
C9—C12—H12B | 109.1 | C34—C33—H6A | 176 (2) |
H12A—C12—H12B | 107.8 | O6A—C33A—C34 | 108.9 (6) |
C13—C12—C9 | 112.7 (2) | O6A—C33A—H7 | 66 (3) |
C13—C12—H12A | 109.1 | O7A—C33A—O6A | 121.0 (7) |
C13—C12—H12B | 109.1 | O7A—C33A—C34 | 130.1 (6) |
C12—C13—H13A | 108.5 | O7A—C33A—H7 | 56 (3) |
C12—C13—H13B | 108.5 | C34—C33A—H7 | 173 (3) |
H13A—C13—H13B | 107.5 | C33A—C34—C33 | 24.4 (3) |
C14—C13—C12 | 115.0 (2) | C35—C34—C33 | 108.6 (4) |
C14—C13—H13A | 108.5 | C35—C34—C33A | 132.9 (4) |
C14—C13—H13B | 108.5 | C39—C34—C33 | 132.4 (4) |
C13—C14—H14A | 109.0 | C39—C34—C33A | 108.1 (4) |
C13—C14—H14B | 109.0 | C39—C34—C35 | 119.0 (3) |
C13—C14—C17 | 113.1 (2) | C34—C35—H35 | 119.5 |
H14A—C14—H14B | 107.8 | C34—C35—C36 | 121.0 (3) |
C17—C14—H14A | 109.0 | C36—C35—H35 | 119.5 |
C17—C14—H14B | 109.0 | C35—C36—H36 | 120.7 |
N3—C15—H15A | 109.5 | C37—C36—C35 | 118.7 (3) |
N3—C15—H15B | 109.5 | C37—C36—H36 | 120.7 |
N3—C15—C16 | 110.8 (2) | O3—C37—C38 | 114.0 (2) |
H15A—C15—H15B | 108.1 | C36—C37—O3 | 125.3 (2) |
C16—C15—H15A | 109.5 | C36—C37—C38 | 120.5 (3) |
C16—C15—H15B | 109.5 | C37—C38—H38 | 120.0 |
C15—C16—H16A | 109.1 | C39—C38—C37 | 120.0 (3) |
C15—C16—H16B | 109.1 | C39—C38—H38 | 120.0 |
C15—C16—C17 | 112.5 (2) | C34—C39—H39 | 119.7 |
H16A—C16—H16B | 107.8 | C38—C39—C34 | 120.6 (3) |
C17—C16—H16A | 109.1 | C38—C39—H39 | 119.7 |
O2—C20—C23—C22 | −48.4 (4) | C11—N2—C6—C3 | −23.3 (4) |
O2—C20—C23—C24 | 124.8 (3) | C11—N2—C7—C8 | 54.5 (3) |
O3—C30—C31—C32 | 178.4 (2) | C12—C9—C10—C11 | 179.2 (2) |
O3—C37—C38—C39 | 179.1 (2) | C12—C13—C14—C17 | 170.0 (2) |
O4—C26—C27—C28 | 0.3 (4) | C13—C14—C17—C16 | 55.3 (3) |
O4—C26—C27—C32 | 179.3 (2) | C13—C14—C17—C18 | 179.0 (2) |
O5—C26—C27—C28 | 179.8 (3) | C14—C17—C18—C19 | −179.4 (2) |
O5—C26—C27—C32 | −1.2 (4) | C15—N3—C19—C18 | −57.8 (3) |
O6—C33—C34—C33A | −174.6 (18) | C15—N3—C20—O2 | 0.1 (4) |
O6—C33—C34—C35 | 6.0 (9) | C15—N3—C20—C23 | 176.5 (2) |
O6—C33—C34—C39 | −174.2 (6) | C15—C16—C17—C14 | 177.9 (2) |
O6A—C33A—C34—C33 | −1.1 (10) | C15—C16—C17—C18 | 52.7 (3) |
O6A—C33A—C34—C35 | −0.2 (8) | C16—C17—C18—C19 | −53.5 (3) |
O6A—C33A—C34—C39 | 179.2 (5) | C17—C18—C19—N3 | 56.1 (3) |
O7—C33—C34—C33A | 5.2 (10) | C19—N3—C15—C16 | 56.8 (3) |
O7—C33—C34—C35 | −174.1 (5) | C19—N3—C20—O2 | 162.5 (3) |
O7—C33—C34—C39 | 5.6 (9) | C19—N3—C20—C23 | −21.1 (4) |
O7A—C33A—C34—C33 | 178.0 (19) | C20—N3—C15—C16 | −138.8 (3) |
O7A—C33A—C34—C35 | 178.9 (6) | C20—N3—C19—C18 | 138.8 (3) |
O7A—C33A—C34—C39 | −1.7 (9) | C20—C23—C24—C25 | −172.5 (3) |
N1—C1—C2—C3 | −0.1 (4) | C21—N4—C25—C24 | 0.5 (5) |
N2—C7—C8—C9 | −53.8 (3) | C21—C22—C23—C20 | 173.9 (3) |
N3—C15—C16—C17 | −54.4 (3) | C21—C22—C23—C24 | 0.3 (4) |
N3—C20—C23—C22 | 135.0 (3) | C22—C23—C24—C25 | 0.8 (4) |
N3—C20—C23—C24 | −51.7 (4) | C23—C24—C25—N4 | −1.2 (5) |
N4—C21—C22—C23 | −1.0 (5) | C25—N4—C21—C22 | 0.6 (5) |
C1—N1—C5—C4 | −1.5 (4) | C26—C27—C28—C29 | −179.1 (2) |
C1—C2—C3—C4 | −1.5 (4) | C26—C27—C32—C31 | 178.4 (2) |
C1—C2—C3—C6 | 171.1 (2) | C27—C28—C29—C30 | 1.3 (4) |
C2—C3—C4—C5 | 1.7 (4) | C28—C27—C32—C31 | −2.5 (4) |
C2—C3—C6—O1 | −43.4 (4) | C28—C29—C30—O3 | −178.5 (2) |
C2—C3—C6—N2 | 139.2 (3) | C28—C29—C30—C31 | −4.1 (4) |
C3—C4—C5—N1 | −0.2 (4) | C29—C30—C31—C32 | 3.5 (4) |
C4—C3—C6—O1 | 128.7 (3) | C30—O3—C37—C36 | −19.1 (4) |
C4—C3—C6—N2 | −48.7 (4) | C30—O3—C37—C38 | 165.1 (2) |
C5—N1—C1—C2 | 1.6 (4) | C30—C31—C32—C27 | −0.2 (4) |
C6—N2—C7—C8 | −145.5 (2) | C32—C27—C28—C29 | 1.9 (4) |
C6—N2—C11—C10 | 146.0 (3) | C33—C34—C35—C36 | −178.1 (4) |
C6—C3—C4—C5 | −170.3 (3) | C33—C34—C39—C38 | 177.0 (5) |
C7—N2—C6—O1 | 2.0 (4) | C33A—C34—C35—C36 | −178.5 (5) |
C7—N2—C6—C3 | 179.3 (2) | C33A—C34—C39—C38 | 177.2 (4) |
C7—N2—C11—C10 | −55.8 (3) | C34—C35—C36—C37 | 1.6 (4) |
C7—C8—C9—C10 | 53.7 (3) | C35—C34—C39—C38 | −3.3 (4) |
C7—C8—C9—C12 | 178.8 (2) | C35—C36—C37—O3 | −179.7 (2) |
C8—C9—C10—C11 | −55.2 (3) | C35—C36—C37—C38 | −4.1 (4) |
C8—C9—C12—C13 | 54.6 (3) | C36—C37—C38—C39 | 3.0 (4) |
C9—C10—C11—N2 | 56.4 (3) | C37—O3—C30—C29 | −38.8 (4) |
C9—C12—C13—C14 | 171.8 (2) | C37—O3—C30—C31 | 146.5 (2) |
C10—C9—C12—C13 | 177.7 (2) | C37—C38—C39—C34 | 0.7 (4) |
C11—N2—C6—O1 | 159.5 (3) | C39—C34—C35—C36 | 2.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N1i | 0.84 | 1.83 | 2.665 (3) | 176 |
O7—H7···N4 | 0.86 (2) | 2.01 (3) | 2.859 (7) | 167 (8) |
O6A—H6A···N4 | 0.86 (2) | 1.79 (2) | 2.652 (7) | 177 (7) |
C1—H1···O7Aii | 0.95 | 2.27 | 3.114 (6) | 147 |
C12—H12B···O2iii | 0.99 | 2.60 | 3.453 (4) | 144 |
C19—H19B···O6iii | 0.99 | 2.47 | 3.326 (6) | 144 |
Symmetry codes: (i) x−1, y, z−2; (ii) −x+1, y+1/2, −z+5/2; (iii) x, −y+5/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···N1i | 0.84 | 1.83 | 2.665 (3) | 175.5 |
O7—H7···N4 | 0.86 (2) | 2.01 (3) | 2.859 (7) | 167 (8) |
O6A—H6A···N4 | 0.86 (2) | 1.79 (2) | 2.652 (7) | 177 (7) |
C1—H1···O7Aii | 0.95 | 2.27 | 3.114 (6) | 147 |
C12—H12B···O2iii | 0.99 | 2.60 | 3.453 (4) | 144 |
C19—H19B···O6iii | 0.99 | 2.47 | 3.326 (6) | 144 |
Symmetry codes: (i) x−1, y, z−2; (ii) −x+1, y+1/2, −z+5/2; (iii) x, −y+5/2, z+1/2. |
Acknowledgements
We gratefully acknowledge Lyman Briggs College of Michigan State University for funding this work. EML thanks the Michigan State University High School Honors Science Program for her participation in this research effort. We thank Dr Rose Tyler for helpful discussions.
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