organic compounds
(S)-2-[(4-Fluorophenyl)formamido]-3-phenylpropanoic acid
aDepartment of Chemistry and Biochemistry, Abilene Christian University, ACU 28132, Abilene, Texas 79699, USA, and bRigaku Americas Corporation, 9009 New Trails Drive, The Woodlands, Texas, 77381, USA
*Correspondence e-mail: Kathleen.Lee@acu.edu
The title compound, C16H14FNO3, was synthesized via solid phase methods; it exhibits monoclinic (P21) symmetry at room temperature. The two independent molecules that comprise the display distinct torsion angles of 173.2 (2) and 72.6 (2)° along the central sp3 C—N bond. In the crystal, hydrogen bonding through N—H⋯O contacts couples the molecules into pairs that align in layers extending parallel to (100) via additional O—H⋯O interactions. The phenyl ring of one independent molecule was found to be disordered over two sets of sites in a 0.55 (3):0.45 (3) ratio.
CCDC reference: 1975451
Structure description
Antibiotic resistance is a major global concern, compounded by the shortage of novel classes of antibiotics in the clinical pipeline (Friedman et al., 2016; Frieri et al., 2017). In order to address the need for new pharmaceuticals and to incorporate drug discovery into the undergraduate curriculum, William Scott and coworkers created the Distributed Drug Discovery (D3) program (Scott & O'Donnell, 2009). D3′s virtual catalogs enumerate sets of amino-acid derivatives that have potential biological activity and that may be synthesized through straightforward combinatorial methods (Scott et al., 2009; Abraham et al., 2017). The D3 Lab 2 procedure targets N-acyl derivatives of natural amino acids in three steps (Dounay et al., 2019). In this paper, we report the use of the D3 procedure to obtain the title compound as a single stereoisomer.
The compound was synthesized via solid phase methods starting from an Fmoc-protected phenylalanine bound to a Wang resin, which was purchased from CreoSalus Advanced Chem Tech as the enantiopure S stereoisomer. The stereocenter remains unchanged during the deprotection, benzoylation, cleavage sequence to form the final product. The of the title compound has been established by effects in the diffraction measurement.
Two unique molecules comprise the . The phenyl ring in molecule 1 is disordered over two slightly different positions. Interestingly, torsion angles measured at the middle of the molecules are quite different; in molecule 1, the C1—N1—C9—C10 angle is 173.2 (2)° and in molecule 2, the analogous C17—N2—C25—C26 angle is 72.6 (2)°. The amino-hydrogen atom on each molecule is hydrogen-bonded to the organic-acid carbonyl O atom on the other molecule (N—H⋯O contacts, Table 1) coupling the molecules in the so that they are positioned on top of each other with a fluoro-substituted ring above and nearly perpendicular to the unsubstituted ring of the partner molecule [mean dihedral angle between the rings of the two molecules = 87 (3)°]. Fig. 2 shows an overlay of the two distinct molecules, highlighting their conformational differences. As shown in Fig. 3, the coupled asymmetric-unit pairs align in chains parallel to [010] via additional hydrogen-bonding interactions between OH organic-acid hydrogen atoms and the amide oxygen atoms in adjacent pairs through the O—H⋯O contacts listed in Table 1. Layers of chains extending parallel to (100) are visible when the packing is viewed along the b axis. The benzene-ring ends of the asymmetric-unit pairs that project out of each hydrogen-bonded chain occupy the voids between coupled asymmetric-unit pairs in the chain layers above and below, allowing closer packing.
Within the molecules the planes containing the benzene rings are rotated with respect to one another by 79.9 (1)° (molecule 1, containing N1—F1) and 89.3 (1)° (molecule 2, containing N2—F2), as shown in Fig. 1Synthesis and crystallization
50 µmol of S-phenylalanine protected with fluorenylmethyloxycarbonyl (Fmoc) and bound to a Wang resin were placed in a fritted vial with screw caps at both ends. The resin was rinsed with three 3 ml aliquots of N-methyl-2-pyrrolidone (NMP) and three 2 ml aliquots of NMP:piperidine (4:1). The bottom of the vial was capped to prevent the acylating reagents from draining from the vial. To the resin was added 1.0 ml of a solution of p-fluorobenzoic acid (0.25 M) and hydroxybenzotriazole (HOBt, 0.25 M) in NMP and 0.5 ml of 0.5 M diisopropylcarbodiimide in NMP. The vial was capped, inverted three times, and allowed to sit. After four days, the vial was uncapped at both ends, and the resin was washed sequentially with two 3 ml portions of NMP, two 3 ml portions of tetrahydrofuran, and three 3 ml portions of dichloromethane. The reaction vial was placed over a collection vial, and the resin was washed twice with 2.0 ml of trifluoroacetic acid–dichloromethane–water (35:60:5) and once with 2.0 ml of dichloromethane. The collection vial containing the combined rinses was placed in a vacuum chamber to remove the solvents. (hexanes:acetone, 75/25 v/v) afforded 12.8 mg of the title compound (89% overall yield from Fmoc–Phe–Wang resin). The purified product was crystallized from a dichloromethane solution layered with a solution of heptane and benzene. 1H NMR (600 MHz, CDCl3/CD3OD) δ 7.73 (m, 2H), 7.13 (m, 3H), 7.10 (m, 4H), 5.05 (t, J = 5.6 Hz, 1H), 3.27 (dd, J = 13.8, 5.7 Hz, 1H), 3.21 (dd, J = 13.8, 5.6 Hz, 1H). 13C NMR (150 MHz, CDCl3/CD3OD) δ 172.23, 166.11, 164.09, 135.77, 129.49, 129.43, 129.29, 128.67, 127.26, 115.78, 53.55, 37.78.
Refinement
Crystal data, data collection and structure . The phenyl ring (C11–C16) of molecule 1 was found to be disordered over two sets of sites in a ratio of 0.55 (3):0.45 (3). The AFIX 66 constraint was applied to both parts of the disordered phenyl ring, and the RIGU rigid body restraint was applied to all non-hydrogen atoms in those rings with σ values of 0.001 for the 1–2 and 1–3 distances.
details are summarized in Table 2Structural data
CCDC reference: 1975451
https://doi.org/10.1107/S2414314620008974/wm4133sup1.cif
contains datablock I. DOI:Supporting information file. DOI: https://doi.org/10.1107/S2414314620008974/wm4133Isup2.cml
Data collection: CrysAlis PRO (Rigaku OD, 2019); cell
CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).C16H14FNO3 | F(000) = 600 |
Mr = 287.28 | Dx = 1.349 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 9.74134 (5) Å | Cell parameters from 40752 reflections |
b = 9.83313 (4) Å | θ = 4.6–73.5° |
c = 14.91737 (6) Å | µ = 0.86 mm−1 |
β = 98.2662 (4)° | T = 100 K |
V = 1414.06 (1) Å3 | Block, colourless |
Z = 4 | 0.56 × 0.21 × 0.12 mm |
Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer | 5671 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5602 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 5.2387 pixels mm-1 | θmax = 73.7°, θmin = 4.6° |
ω scans | h = −11→12 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2019) | k = −12→12 |
Tmin = 0.452, Tmax = 1.000 | l = −18→18 |
53742 measured reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.1344P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.028 | (Δ/σ)max = 0.001 |
wR(F2) = 0.079 | Δρmax = 0.16 e Å−3 |
S = 1.05 | Δρmin = −0.12 e Å−3 |
5671 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
421 parameters | Extinction coefficient: 0.0068 (5) |
355 restraints | Absolute structure: Flack x determined using 2580 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: −0.05 (3) |
Hydrogen site location: mixed |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O4 | 0.55896 (13) | 0.60198 (15) | 0.89050 (9) | 0.0473 (3) | |
O5 | 0.38969 (13) | 0.57893 (16) | 0.97497 (8) | 0.0464 (3) | |
H5 | 0.4369 | 0.6359 | 1.0082 | 0.070* | |
O3 | 0.47124 (17) | 0.78037 (16) | 0.57577 (9) | 0.0532 (4) | |
O2 | 0.49339 (14) | 0.45890 (15) | 0.60468 (9) | 0.0477 (3) | |
N2 | 0.43835 (15) | 0.38567 (14) | 0.78447 (10) | 0.0362 (3) | |
O6 | 0.51088 (15) | 0.27881 (15) | 0.91538 (8) | 0.0474 (3) | |
O1 | 0.64625 (15) | 0.49117 (17) | 0.50928 (9) | 0.0543 (4) | |
H1 | 0.6083 | 0.4219 | 0.4837 | 0.081* | |
F1 | 0.14855 (17) | 1.06807 (19) | 0.85687 (12) | 0.0825 (5) | |
F2 | 0.83586 (18) | −0.06630 (18) | 0.65856 (14) | 0.0876 (5) | |
N1 | 0.59204 (17) | 0.69008 (16) | 0.69952 (10) | 0.0401 (3) | |
C18 | 0.59847 (18) | 0.19811 (17) | 0.78350 (12) | 0.0387 (4) | |
C25 | 0.35323 (17) | 0.48177 (16) | 0.82684 (10) | 0.0334 (3) | |
H25 | 0.3192 | 0.5505 | 0.7794 | 0.040* | |
C8 | 0.59457 (18) | 0.51500 (18) | 0.58414 (11) | 0.0370 (3) | |
C24 | 0.44635 (16) | 0.55878 (17) | 0.90178 (10) | 0.0334 (3) | |
C17 | 0.51291 (18) | 0.28963 (17) | 0.83285 (11) | 0.0360 (3) | |
C23 | 0.5622 (2) | 0.16621 (18) | 0.69210 (14) | 0.0439 (4) | |
H23 | 0.4815 | 0.2053 | 0.6587 | 0.053* | |
C1 | 0.4897 (2) | 0.76851 (18) | 0.65954 (11) | 0.0399 (4) | |
C27 | 0.11085 (18) | 0.50384 (19) | 0.87908 (11) | 0.0380 (3) | |
C2 | 0.3995 (2) | 0.84212 (18) | 0.71611 (12) | 0.0408 (4) | |
C26 | 0.22470 (19) | 0.41301 (18) | 0.85338 (13) | 0.0421 (4) | |
H26A | 0.1839 | 0.3551 | 0.8021 | 0.050* | |
H26B | 0.2551 | 0.3519 | 0.9052 | 0.050* | |
C22 | 0.6434 (2) | 0.0778 (2) | 0.64961 (16) | 0.0532 (5) | |
H22 | 0.6198 | 0.0564 | 0.5872 | 0.064* | |
C32 | −0.0009 (2) | 0.4410 (2) | 0.91043 (13) | 0.0488 (4) | |
H32 | −0.0039 | 0.3446 | 0.9139 | 0.059* | |
C9 | 0.67988 (19) | 0.61896 (19) | 0.64353 (11) | 0.0383 (4) | |
H9 | 0.7187 | 0.6866 | 0.6038 | 0.046* | |
C19 | 0.7173 (2) | 0.1409 (2) | 0.83170 (15) | 0.0495 (4) | |
H19 | 0.7435 | 0.1631 | 0.8938 | 0.059* | |
C10 | 0.8002 (2) | 0.5494 (2) | 0.70428 (12) | 0.0483 (4) | |
H10C | 0.8406 | 0.6155 | 0.7507 | 0.058* | 0.45 (3) |
H10D | 0.7619 | 0.4732 | 0.7363 | 0.058* | 0.45 (3) |
H10A | 0.7621 | 0.4755 | 0.7385 | 0.058* | 0.55 (3) |
H10B | 0.8443 | 0.6165 | 0.7488 | 0.058* | 0.55 (3) |
C21 | 0.7572 (2) | 0.0226 (2) | 0.69956 (18) | 0.0567 (5) | |
C28 | 0.1109 (2) | 0.6446 (2) | 0.87296 (14) | 0.0457 (4) | |
H28 | 0.1847 | 0.6897 | 0.8500 | 0.055* | |
C31 | −0.1082 (2) | 0.5172 (3) | 0.93667 (15) | 0.0586 (5) | |
H31 | −0.1840 | 0.4727 | 0.9577 | 0.070* | |
C4 | 0.3585 (2) | 0.9521 (2) | 0.85435 (15) | 0.0539 (5) | |
H4 | 0.3875 | 0.9752 | 0.9160 | 0.065* | |
C7 | 0.2683 (2) | 0.8821 (2) | 0.67540 (14) | 0.0514 (4) | |
H7 | 0.2366 | 0.8567 | 0.6145 | 0.062* | |
C29 | 0.0034 (2) | 0.7198 (2) | 0.90028 (15) | 0.0553 (5) | |
H29 | 0.0051 | 0.8163 | 0.8966 | 0.066* | |
C3 | 0.4435 (2) | 0.8773 (2) | 0.80636 (13) | 0.0461 (4) | |
H3 | 0.5325 | 0.8497 | 0.8350 | 0.055* | |
C16B | 0.9064 (12) | 0.3556 (8) | 0.6455 (9) | 0.063 (2) | 0.45 (3) |
H16B | 0.8344 | 0.3050 | 0.6667 | 0.076* | 0.45 (3) |
C15B | 1.0046 (15) | 0.2896 (8) | 0.6023 (8) | 0.071 (2) | 0.45 (3) |
H15B | 0.9998 | 0.1938 | 0.5939 | 0.085* | 0.45 (3) |
C14B | 1.1099 (13) | 0.3636 (14) | 0.5712 (6) | 0.064 (2) | 0.45 (3) |
H14B | 1.1770 | 0.3184 | 0.5417 | 0.077* | 0.45 (3) |
C13B | 1.1169 (8) | 0.5037 (13) | 0.5835 (7) | 0.073 (2) | 0.45 (3) |
H13B | 1.1889 | 0.5543 | 0.5623 | 0.087* | 0.45 (3) |
C12B | 1.0187 (10) | 0.5698 (8) | 0.6268 (7) | 0.054 (2) | 0.45 (3) |
H12B | 1.0235 | 0.6655 | 0.6351 | 0.065* | 0.45 (3) |
C11B | 0.9134 (10) | 0.4957 (8) | 0.6578 (9) | 0.0461 (19) | 0.45 (3) |
C6 | 0.1834 (2) | 0.9586 (3) | 0.72273 (17) | 0.0600 (5) | |
H6 | 0.0943 | 0.9871 | 0.6948 | 0.072* | |
C5 | 0.2313 (2) | 0.9922 (2) | 0.81097 (16) | 0.0565 (5) | |
C20 | 0.7975 (2) | 0.0519 (3) | 0.78943 (18) | 0.0608 (5) | |
H20 | 0.8785 | 0.0119 | 0.8219 | 0.073* | |
C30 | −0.1054 (2) | 0.6563 (3) | 0.93251 (15) | 0.0580 (5) | |
H30 | −0.1780 | 0.7084 | 0.9517 | 0.070* | |
C16A | 1.0068 (9) | 0.5848 (5) | 0.6299 (7) | 0.068 (3) | 0.55 (3) |
H16A | 0.9943 | 0.6783 | 0.6424 | 0.082* | 0.55 (3) |
C15A | 1.1190 (7) | 0.5437 (10) | 0.5885 (6) | 0.0672 (17) | 0.55 (3) |
H15A | 1.1832 | 0.6092 | 0.5728 | 0.081* | 0.55 (3) |
C14A | 1.1373 (7) | 0.4068 (12) | 0.5702 (5) | 0.0602 (16) | 0.55 (3) |
H14A | 1.2140 | 0.3788 | 0.5419 | 0.072* | 0.55 (3) |
C13A | 1.0434 (10) | 0.3110 (7) | 0.5931 (6) | 0.0617 (17) | 0.55 (3) |
H13A | 1.0559 | 0.2175 | 0.5806 | 0.074* | 0.55 (3) |
C12A | 0.9312 (9) | 0.3521 (6) | 0.6345 (7) | 0.0571 (16) | 0.55 (3) |
H12A | 0.8670 | 0.2866 | 0.6502 | 0.068* | 0.55 (3) |
C11A | 0.9129 (8) | 0.4889 (7) | 0.6528 (7) | 0.0437 (15) | 0.55 (3) |
H1A | 0.594 (2) | 0.665 (2) | 0.7566 (16) | 0.047 (6)* | |
H2 | 0.452 (2) | 0.397 (2) | 0.7303 (16) | 0.044 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0360 (6) | 0.0599 (8) | 0.0469 (7) | −0.0066 (5) | 0.0088 (5) | −0.0043 (6) |
O5 | 0.0425 (6) | 0.0618 (8) | 0.0359 (6) | −0.0085 (6) | 0.0089 (5) | −0.0125 (6) |
O3 | 0.0718 (10) | 0.0542 (8) | 0.0339 (6) | 0.0109 (7) | 0.0087 (6) | 0.0057 (6) |
O2 | 0.0519 (7) | 0.0538 (8) | 0.0388 (6) | −0.0108 (6) | 0.0115 (5) | −0.0034 (5) |
N2 | 0.0439 (8) | 0.0371 (7) | 0.0288 (6) | 0.0068 (6) | 0.0089 (5) | 0.0016 (5) |
O6 | 0.0582 (8) | 0.0501 (7) | 0.0348 (6) | 0.0137 (6) | 0.0094 (5) | 0.0083 (5) |
O1 | 0.0544 (8) | 0.0741 (10) | 0.0366 (6) | −0.0145 (7) | 0.0135 (6) | −0.0184 (6) |
F1 | 0.0859 (10) | 0.0780 (10) | 0.0923 (10) | 0.0130 (8) | 0.0431 (8) | −0.0129 (9) |
F2 | 0.0745 (10) | 0.0735 (10) | 0.1229 (13) | 0.0176 (8) | 0.0420 (9) | −0.0265 (9) |
N1 | 0.0499 (8) | 0.0421 (7) | 0.0286 (6) | −0.0001 (6) | 0.0073 (6) | −0.0007 (6) |
C18 | 0.0401 (8) | 0.0325 (7) | 0.0448 (8) | 0.0001 (6) | 0.0108 (6) | 0.0036 (6) |
C25 | 0.0363 (7) | 0.0331 (7) | 0.0308 (7) | 0.0035 (6) | 0.0052 (6) | 0.0006 (6) |
C8 | 0.0404 (8) | 0.0428 (8) | 0.0277 (7) | 0.0012 (6) | 0.0043 (6) | 0.0015 (6) |
C24 | 0.0333 (7) | 0.0344 (7) | 0.0324 (7) | 0.0032 (6) | 0.0047 (6) | 0.0013 (6) |
C17 | 0.0383 (8) | 0.0346 (7) | 0.0356 (7) | 0.0000 (6) | 0.0066 (6) | 0.0027 (6) |
C23 | 0.0464 (9) | 0.0369 (8) | 0.0492 (9) | 0.0001 (7) | 0.0104 (7) | −0.0049 (7) |
C1 | 0.0498 (9) | 0.0356 (8) | 0.0347 (7) | −0.0046 (7) | 0.0076 (6) | 0.0018 (6) |
C27 | 0.0348 (8) | 0.0444 (8) | 0.0340 (8) | −0.0006 (6) | 0.0021 (6) | −0.0025 (6) |
C2 | 0.0494 (9) | 0.0346 (8) | 0.0397 (8) | −0.0052 (7) | 0.0108 (6) | 0.0021 (6) |
C26 | 0.0385 (8) | 0.0357 (8) | 0.0528 (10) | −0.0026 (6) | 0.0095 (7) | −0.0025 (7) |
C22 | 0.0548 (10) | 0.0434 (9) | 0.0649 (11) | −0.0047 (8) | 0.0206 (8) | −0.0140 (9) |
C32 | 0.0439 (9) | 0.0611 (11) | 0.0419 (9) | −0.0029 (8) | 0.0078 (7) | 0.0062 (8) |
C9 | 0.0429 (8) | 0.0433 (8) | 0.0290 (7) | −0.0032 (7) | 0.0067 (6) | −0.0016 (6) |
C19 | 0.0444 (9) | 0.0516 (10) | 0.0537 (10) | 0.0078 (8) | 0.0111 (8) | 0.0080 (8) |
C10 | 0.0443 (9) | 0.0643 (11) | 0.0348 (8) | 0.0009 (8) | 0.0012 (7) | −0.0016 (8) |
C21 | 0.0515 (10) | 0.0446 (10) | 0.0796 (12) | 0.0025 (8) | 0.0283 (9) | −0.0072 (9) |
C28 | 0.0397 (9) | 0.0441 (9) | 0.0533 (10) | 0.0010 (7) | 0.0064 (8) | −0.0053 (7) |
C31 | 0.0433 (10) | 0.0867 (13) | 0.0474 (10) | 0.0006 (9) | 0.0124 (8) | −0.0001 (10) |
C4 | 0.0642 (11) | 0.0496 (10) | 0.0509 (10) | −0.0098 (8) | 0.0190 (8) | −0.0115 (8) |
C7 | 0.0518 (10) | 0.0580 (11) | 0.0453 (9) | −0.0001 (8) | 0.0104 (7) | 0.0068 (8) |
C29 | 0.0485 (10) | 0.0570 (11) | 0.0589 (12) | 0.0110 (8) | 0.0026 (9) | −0.0134 (9) |
C3 | 0.0527 (10) | 0.0421 (9) | 0.0443 (9) | −0.0075 (8) | 0.0093 (7) | −0.0043 (7) |
C16B | 0.066 (4) | 0.057 (3) | 0.071 (4) | 0.003 (2) | 0.024 (3) | −0.004 (2) |
C15B | 0.075 (5) | 0.055 (3) | 0.090 (4) | 0.002 (2) | 0.036 (4) | −0.002 (3) |
C14B | 0.072 (4) | 0.049 (4) | 0.078 (4) | 0.004 (3) | 0.033 (3) | −0.004 (3) |
C13B | 0.075 (3) | 0.050 (4) | 0.103 (5) | 0.000 (3) | 0.049 (4) | −0.005 (3) |
C12B | 0.052 (3) | 0.053 (3) | 0.058 (4) | 0.001 (2) | 0.014 (3) | −0.006 (2) |
C11B | 0.045 (3) | 0.057 (3) | 0.036 (4) | 0.0017 (18) | 0.002 (3) | −0.002 (2) |
C6 | 0.0547 (11) | 0.0649 (13) | 0.0633 (11) | 0.0081 (10) | 0.0183 (9) | 0.0095 (9) |
C5 | 0.0616 (11) | 0.0490 (10) | 0.0643 (11) | −0.0014 (9) | 0.0274 (9) | −0.0010 (9) |
C20 | 0.0477 (10) | 0.0570 (11) | 0.0810 (13) | 0.0138 (9) | 0.0205 (9) | 0.0074 (10) |
C30 | 0.0442 (10) | 0.0827 (13) | 0.0471 (10) | 0.0104 (9) | 0.0070 (8) | −0.0144 (9) |
C16A | 0.063 (3) | 0.057 (3) | 0.092 (6) | −0.006 (2) | 0.031 (4) | −0.006 (2) |
C15A | 0.063 (3) | 0.056 (3) | 0.088 (4) | −0.009 (2) | 0.029 (3) | −0.007 (2) |
C14A | 0.056 (3) | 0.057 (3) | 0.071 (3) | −0.008 (2) | 0.023 (2) | −0.002 (3) |
C13A | 0.059 (3) | 0.048 (2) | 0.083 (4) | −0.0027 (19) | 0.029 (2) | 0.000 (2) |
C12A | 0.054 (3) | 0.049 (2) | 0.072 (4) | −0.0034 (16) | 0.023 (3) | −0.0009 (18) |
C11A | 0.041 (2) | 0.051 (2) | 0.037 (3) | −0.0016 (15) | −0.001 (2) | −0.0007 (18) |
O4—C24 | 1.210 (2) | C10—H10A | 0.9900 |
O5—H5 | 0.8400 | C10—H10B | 0.9900 |
O5—C24 | 1.307 (2) | C10—C11B | 1.482 (6) |
O3—C1 | 1.242 (2) | C10—C11A | 1.546 (5) |
O2—C8 | 1.207 (2) | C21—C20 | 1.372 (4) |
N2—C25 | 1.460 (2) | C28—H28 | 0.9500 |
N2—C17 | 1.338 (2) | C28—C29 | 1.391 (3) |
N2—H2 | 0.84 (2) | C31—H31 | 0.9500 |
O6—C17 | 1.239 (2) | C31—C30 | 1.369 (4) |
O1—H1 | 0.8400 | C4—H4 | 0.9500 |
O1—C8 | 1.310 (2) | C4—C3 | 1.382 (3) |
F1—C5 | 1.354 (3) | C4—C5 | 1.371 (3) |
F2—C21 | 1.364 (2) | C7—H7 | 0.9500 |
N1—C1 | 1.332 (2) | C7—C6 | 1.384 (3) |
N1—C9 | 1.457 (2) | C29—H29 | 0.9500 |
N1—H1A | 0.89 (2) | C29—C30 | 1.375 (3) |
C18—C17 | 1.491 (2) | C3—H3 | 0.9500 |
C18—C23 | 1.394 (3) | C16B—H16B | 0.9500 |
C18—C19 | 1.390 (3) | C16B—C15B | 1.3900 |
C25—H25 | 1.0000 | C16B—C11B | 1.3900 |
C25—C24 | 1.534 (2) | C15B—H15B | 0.9500 |
C25—C26 | 1.525 (2) | C15B—C14B | 1.3900 |
C8—C9 | 1.520 (2) | C14B—H14B | 0.9500 |
C23—H23 | 0.9500 | C14B—C13B | 1.3900 |
C23—C22 | 1.388 (3) | C13B—H13B | 0.9500 |
C1—C2 | 1.490 (3) | C13B—C12B | 1.3900 |
C27—C26 | 1.516 (3) | C12B—H12B | 0.9500 |
C27—C32 | 1.390 (3) | C12B—C11B | 1.3900 |
C27—C28 | 1.387 (3) | C6—H6 | 0.9500 |
C2—C7 | 1.391 (3) | C6—C5 | 1.372 (3) |
C2—C3 | 1.396 (3) | C20—H20 | 0.9500 |
C26—H26A | 0.9900 | C30—H30 | 0.9500 |
C26—H26B | 0.9900 | C16A—H16A | 0.9500 |
C22—H22 | 0.9500 | C16A—C15A | 1.3900 |
C22—C21 | 1.357 (3) | C16A—C11A | 1.3900 |
C32—H32 | 0.9500 | C15A—H15A | 0.9500 |
C32—C31 | 1.388 (3) | C15A—C14A | 1.3900 |
C9—H9 | 1.0000 | C14A—H14A | 0.9500 |
C9—C10 | 1.536 (3) | C14A—C13A | 1.3900 |
C19—H19 | 0.9500 | C13A—H13A | 0.9500 |
C19—C20 | 1.384 (3) | C13A—C12A | 1.3900 |
C10—H10C | 0.9900 | C12A—H12A | 0.9500 |
C10—H10D | 0.9900 | C12A—C11A | 1.3900 |
C24—O5—H5 | 109.5 | C11A—C10—H10B | 108.6 |
C25—N2—H2 | 120.2 (16) | F2—C21—C20 | 118.2 (2) |
C17—N2—C25 | 121.44 (14) | C22—C21—F2 | 118.5 (2) |
C17—N2—H2 | 117.7 (16) | C22—C21—C20 | 123.3 (2) |
C8—O1—H1 | 109.5 | C27—C28—H28 | 119.9 |
C1—N1—C9 | 118.99 (14) | C27—C28—C29 | 120.3 (2) |
C1—N1—H1A | 120.1 (15) | C29—C28—H28 | 119.9 |
C9—N1—H1A | 119.1 (15) | C32—C31—H31 | 119.8 |
C23—C18—C17 | 122.54 (16) | C30—C31—C32 | 120.4 (2) |
C19—C18—C17 | 118.14 (17) | C30—C31—H31 | 119.8 |
C19—C18—C23 | 119.32 (17) | C3—C4—H4 | 120.8 |
N2—C25—H25 | 106.4 | C5—C4—H4 | 120.8 |
N2—C25—C24 | 108.77 (13) | C5—C4—C3 | 118.5 (2) |
N2—C25—C26 | 111.36 (14) | C2—C7—H7 | 119.7 |
C24—C25—H25 | 106.4 | C6—C7—C2 | 120.7 (2) |
C26—C25—H25 | 106.4 | C6—C7—H7 | 119.7 |
C26—C25—C24 | 116.82 (14) | C28—C29—H29 | 119.6 |
O2—C8—O1 | 124.23 (16) | C30—C29—C28 | 120.8 (2) |
O2—C8—C9 | 123.89 (15) | C30—C29—H29 | 119.6 |
O1—C8—C9 | 111.86 (15) | C2—C3—H3 | 119.7 |
O4—C24—O5 | 124.25 (16) | C4—C3—C2 | 120.5 (2) |
O4—C24—C25 | 121.64 (15) | C4—C3—H3 | 119.7 |
O5—C24—C25 | 114.01 (14) | C15B—C16B—H16B | 120.0 |
N2—C17—C18 | 117.28 (14) | C15B—C16B—C11B | 120.0 |
O6—C17—N2 | 120.79 (16) | C11B—C16B—H16B | 120.0 |
O6—C17—C18 | 121.93 (15) | C16B—C15B—H15B | 120.0 |
C18—C23—H23 | 119.8 | C14B—C15B—C16B | 120.0 |
C22—C23—C18 | 120.45 (19) | C14B—C15B—H15B | 120.0 |
C22—C23—H23 | 119.8 | C15B—C14B—H14B | 120.0 |
O3—C1—N1 | 119.71 (17) | C15B—C14B—C13B | 120.0 |
O3—C1—C2 | 120.83 (17) | C13B—C14B—H14B | 120.0 |
N1—C1—C2 | 119.46 (15) | C14B—C13B—H13B | 120.0 |
C32—C27—C26 | 117.39 (17) | C12B—C13B—C14B | 120.0 |
C28—C27—C26 | 124.34 (17) | C12B—C13B—H13B | 120.0 |
C28—C27—C32 | 118.28 (19) | C13B—C12B—H12B | 120.0 |
C7—C2—C1 | 118.01 (17) | C13B—C12B—C11B | 120.0 |
C7—C2—C3 | 119.05 (19) | C11B—C12B—H12B | 120.0 |
C3—C2—C1 | 122.88 (18) | C16B—C11B—C10 | 112.9 (6) |
C25—C26—H26A | 107.9 | C12B—C11B—C10 | 127.1 (6) |
C25—C26—H26B | 107.9 | C12B—C11B—C16B | 120.0 |
C27—C26—C25 | 117.55 (15) | C7—C6—H6 | 120.8 |
C27—C26—H26A | 107.9 | C5—C6—C7 | 118.4 (2) |
C27—C26—H26B | 107.9 | C5—C6—H6 | 120.8 |
H26A—C26—H26B | 107.2 | F1—C5—C4 | 118.9 (2) |
C23—C22—H22 | 120.9 | F1—C5—C6 | 118.3 (2) |
C21—C22—C23 | 118.3 (2) | C4—C5—C6 | 122.9 (2) |
C21—C22—H22 | 120.9 | C19—C20—H20 | 120.8 |
C27—C32—H32 | 119.6 | C21—C20—C19 | 118.5 (2) |
C31—C32—C27 | 120.8 (2) | C21—C20—H20 | 120.8 |
C31—C32—H32 | 119.6 | C31—C30—C29 | 119.4 (2) |
N1—C9—C8 | 109.88 (14) | C31—C30—H30 | 120.3 |
N1—C9—H9 | 108.9 | C29—C30—H30 | 120.3 |
N1—C9—C10 | 109.69 (14) | C15A—C16A—H16A | 120.0 |
C8—C9—H9 | 108.9 | C15A—C16A—C11A | 120.0 |
C8—C9—C10 | 110.57 (16) | C11A—C16A—H16A | 120.0 |
C10—C9—H9 | 108.9 | C16A—C15A—H15A | 120.0 |
C18—C19—H19 | 119.9 | C14A—C15A—C16A | 120.0 |
C20—C19—C18 | 120.2 (2) | C14A—C15A—H15A | 120.0 |
C20—C19—H19 | 119.9 | C15A—C14A—H14A | 120.0 |
C9—C10—H10C | 108.3 | C15A—C14A—C13A | 120.0 |
C9—C10—H10D | 108.3 | C13A—C14A—H14A | 120.0 |
C9—C10—H10A | 108.6 | C14A—C13A—H13A | 120.0 |
C9—C10—H10B | 108.6 | C12A—C13A—C14A | 120.0 |
C9—C10—C11A | 114.5 (5) | C12A—C13A—H13A | 120.0 |
H10C—C10—H10D | 107.4 | C13A—C12A—H12A | 120.0 |
H10A—C10—H10B | 107.6 | C13A—C12A—C11A | 120.0 |
C11B—C10—C9 | 116.0 (6) | C11A—C12A—H12A | 120.0 |
C11B—C10—H10C | 108.3 | C16A—C11A—C10 | 113.7 (5) |
C11B—C10—H10D | 108.3 | C12A—C11A—C10 | 126.2 (5) |
C11A—C10—H10A | 108.6 | C12A—C11A—C16A | 120.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O6i | 0.84 | 1.83 | 2.6497 (18) | 163 |
O1—H1···O3ii | 0.84 | 1.77 | 2.607 (2) | 177 |
N1—H1A···O4 | 0.89 (2) | 2.16 (2) | 3.039 (2) | 170 (2) |
N2—H2···O2 | 0.84 (2) | 2.06 (2) | 2.900 (2) | 170 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+2; (ii) −x+1, y−1/2, −z+1. |
Acknowledgements
NMR data were collected by Dr Joseph Ready and Dr Feng Lin at UT Southwestern Medical Center, Dallas, Texas.
Funding information
Funding for this research was provided by: The Welch Foundation (grant No. R-0021); Abilene Christian University Office of Undergraduate Research; Abilene Christian University Research Council.
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