research communications
of 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium 2-(4-isobutylphenyl)propanoate: a simple organic salt of racemic ibuprofen
aDepartment of Chemistry and Chemical Engineering, Minjiang University, Fuzhou 350108, People's Republic of China
*Correspondence e-mail: lby@mju.edu.cn
In the title organic salt of ibuprofen with trometamol, C4H12NO3+·C13H17O2−, the carboxylic acid group of ibuprofen has transferred its proton to the amino N atom of trometamol. In the crystal, the trometamol cations are linked via N—H⋯O hydrogen bonds, forming chains along [001]. To these chains are attached the ibuprofen anions via O—H⋯O and N—H⋯O hydrogen bonds. The chains are linked via further N—H⋯O and O—H⋯O hydrogen bonds, forming sheets parallel to (100). Two C atoms of the propanoate substituent in the ibuprofen anion are disordered over two sets of sites and were refined with a fixed occupancy ratio of 0.7:0.3.
Keywords: crystal structure; ibuprofen; trometamol; molecular salt; hydrogen bonding; chains; sheets.
CCDC reference: 1410786
1. Chemical context
Salt formation is an effective approach for modifying the properties of active pharmaceutical ingredients (APIs) (Childs et al., 2007). Tris(hydroxymethyl)amino methane, commonly called trometamol, has been successfully exploited for improving the properties of APIs such as ketoprofen (Zippel & Wagenitz, 2006). In this study, trometamol was employed to crystallize with ibuprofen, giving rise to a new crystalline form, whose is reported on herein.
2. Structural commentary
The molecular structure of the title molecular salt is shown in Fig. 1. From difference Fourier maps, it was shown that the carboxylic group of ibuprofen has transferred its proton to the amino N atom of trometamol. This is supported by the C—O bond distances of the carboxylate group of the ibuprofen anion, which are 1.252 (2) and 1.251 (2) Å for C1—O1 and C1—O2, respectively. The carboxylate anion interacts with one hydroxyl group of the trometamol cation through a strong hydrogen bond [O5⋯O2 = 2.730 (2) Å; Table 1]. There also exist hydrogen-bonding interactions between the carboxylate anion and aminium H atoms of the cation [N1⋯O1 = 2.763 (2) Å; Table 1].
3. Supramolecular features
In the crystal, the trometamol cations are linked via N—H⋯O hydrogen bonds, forming chains along [010]; Table 1 and Fig. 2. To these chains are attached the ibuprofen anions via N—H⋯O and O—H⋯O hydrogen bonds. The chains are linked via further O—H⋯O and N—H⋯O hydrogen bonds, forming sheets parallel to (100); Table 1 and Fig. 3.
4. Database survey
A search of the Cambridge Structural Database (Version 5.36, May 2015; Groom & Allen, 2014) revealed only one hit for organic salts of racemic ibuprofen, viz. benzylammonium 2-(4-isobutylphenyl)propionate 2-(4-isobutylphenyl)propionic acid (refcode VUCHUX; Molnár et al., 2009). In fact, it is a salt based on ibuprofen and the organic salt (Sun, 2013). The title compound is the first of a simple organic salt of racemic ibuprofen.
5. Synthesis and crystallization
Ibuprofen (206 mg, 1 mmol) and trometamol (121 mg, 1 mmol) were dissolved in methanol (15 mL). The resulting solution was kept in air and after several days colorless plate-like crystals were obtained.
6. Refinement
Crystal data, data collection and structure . The hydroxyl and and aminium H atoms were located in difference Fourier maps and freely refined. Two C atoms, C3 and C2, of the propanoate substituent in the ibuprofen anion are disordered over two sets of sites (C3/C3′and C2/C2′) and were refined with a fixed occupancy ratio of 0.7:0.3. H atoms H2 and H2′ were refined with distance restraints C—H = 0.98 (2) Å with Uiso(H) = 1.2Ueq(C). The remainder of the C-bound H atoms were positioned geometrically and refined as riding atoms: C—H = 0.95–1.00 Å with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.
details are summarized in Table 2
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Supporting information
CCDC reference: 1410786
https://doi.org/10.1107/S2056989015012979/su5165sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012979/su5165Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012979/su5165Isup3.cml
Data collection: CrystalClear (Rigaku, 2000); cell
CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C4H12NO3+·C13H17O2− | F(000) = 712 |
Mr = 327.41 | Dx = 1.205 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.523 (7) Å | Cell parameters from 4551 reflections |
b = 10.400 (4) Å | θ = 2.8–27.5° |
c = 9.976 (4) Å | µ = 0.09 mm−1 |
β = 97.032 (7)° | T = 173 K |
V = 1804.3 (12) Å3 | Plate, colorless |
Z = 4 | 0.29 × 0.22 × 0.04 mm |
Rigaku Mercury CCD diffractometer | 4096 independent reflections |
Radiation source: fine-focus sealed tube | 3391 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
CCD_Profile_fitting scans | h = −22→22 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000) | k = −13→13 |
Tmin = 0.914, Tmax = 1.000 | l = −12→12 |
13747 measured reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.4122P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
4096 reflections | Δρmax = 0.22 e Å−3 |
260 parameters | Δρmin = −0.23 e Å−3 |
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) | |
O1 | 0.11773 (7) | 0.77640 (11) | 0.78429 (13) | 0.0439 (3) | |
O2 | 0.13430 (7) | 0.58002 (12) | 0.71039 (15) | 0.0544 (4) | |
C1 | 0.15768 (10) | 0.67741 (15) | 0.7767 (2) | 0.0422 (4) | |
C2 | 0.23375 (17) | 0.6782 (3) | 0.8754 (4) | 0.0408 (6) | 0.7 |
H2 | 0.2182 (17) | 0.670 (3) | 0.966 (2) | 0.049* | 0.7 |
C3 | 0.28440 (19) | 0.5630 (3) | 0.8537 (4) | 0.0610 (9) | 0.7 |
H3A | 0.2992 | 0.5660 | 0.7622 | 0.091* | 0.7 |
H3B | 0.2559 | 0.4835 | 0.8652 | 0.091* | 0.7 |
H3C | 0.3307 | 0.5654 | 0.9197 | 0.091* | 0.7 |
C2' | 0.2464 (4) | 0.6735 (7) | 0.8061 (9) | 0.0417 (16) | 0.3 |
H2' | 0.271 (3) | 0.616 (2) | 0.746 (6) | 0.050* | 0.3 |
C3' | 0.2585 (5) | 0.5894 (9) | 0.9312 (11) | 0.070 (2) | 0.3 |
H3'1 | 0.3115 | 0.5989 | 0.9744 | 0.105* | 0.3 |
H3'2 | 0.2490 | 0.4993 | 0.9055 | 0.105* | 0.3 |
H3'3 | 0.2228 | 0.6156 | 0.9945 | 0.105* | 0.3 |
C4 | 0.27435 (10) | 0.80792 (18) | 0.8575 (2) | 0.0542 (5) | |
C5 | 0.26039 (11) | 0.9010 (2) | 0.9485 (2) | 0.0540 (5) | |
H5 | 0.2281 | 0.8817 | 1.0157 | 0.065* | |
C6 | 0.29208 (11) | 1.0220 (2) | 0.9450 (2) | 0.0548 (5) | |
H6 | 0.2825 | 1.0830 | 1.0118 | 0.066* | |
C7 | 0.32041 (12) | 0.8410 (2) | 0.7599 (3) | 0.0667 (6) | |
H7 | 0.3315 | 0.7785 | 0.6955 | 0.080* | |
C8 | 0.35065 (13) | 0.9638 (2) | 0.7543 (3) | 0.0682 (6) | |
H8 | 0.3813 | 0.9843 | 0.6850 | 0.082* | |
C9 | 0.33732 (11) | 1.05711 (19) | 0.8470 (2) | 0.0549 (5) | |
C10 | 0.37079 (14) | 1.1906 (2) | 0.8433 (3) | 0.0768 (7) | |
H10A | 0.3344 | 1.2522 | 0.8768 | 0.092* | |
H10B | 0.3755 | 1.2131 | 0.7482 | 0.092* | |
C11 | 0.44861 (14) | 1.2067 (2) | 0.9256 (3) | 0.0768 (7) | |
H11 | 0.4438 | 1.1754 | 1.0190 | 0.092* | |
C12 | 0.4706 (2) | 1.3480 (3) | 0.9369 (4) | 0.1136 (12) | |
H12A | 0.4710 | 1.3842 | 0.8463 | 0.170* | |
H12B | 0.5219 | 1.3565 | 0.9878 | 0.170* | |
H12C | 0.4331 | 1.3945 | 0.9839 | 0.170* | |
C13 | 0.51137 (16) | 1.1303 (3) | 0.8743 (4) | 0.0991 (10) | |
H13A | 0.5186 | 1.1600 | 0.7834 | 0.149* | |
H13B | 0.4973 | 1.0391 | 0.8708 | 0.149* | |
H13C | 0.5593 | 1.1419 | 0.9348 | 0.149* | |
O3 | −0.15157 (8) | 0.82574 (12) | 0.84440 (14) | 0.0511 (4) | |
H3 | −0.1538 (14) | 0.910 (2) | 0.825 (2) | 0.081 (8)* | |
O4 | −0.08544 (7) | 0.44727 (12) | 0.91701 (13) | 0.0419 (3) | |
H4 | −0.0903 (12) | 0.387 (2) | 0.868 (2) | 0.066 (7)* | |
O5 | −0.00842 (7) | 0.64538 (11) | 0.58848 (12) | 0.0397 (3) | |
H5A | 0.0387 (12) | 0.6268 (18) | 0.616 (2) | 0.059 (6)* | |
N1 | −0.01557 (8) | 0.68283 (13) | 0.87045 (14) | 0.0313 (3) | |
H1A | 0.0234 (12) | 0.7199 (19) | 0.826 (2) | 0.049 (5)* | |
H1B | 0.0080 (11) | 0.6126 (19) | 0.9193 (19) | 0.044 (5)* | |
H1C | −0.0290 (11) | 0.745 (2) | 0.927 (2) | 0.046 (5)* | |
C14 | −0.13080 (10) | 0.75903 (15) | 0.73082 (18) | 0.0411 (4) | |
H14A | −0.0997 | 0.8157 | 0.6790 | 0.049* | |
H14B | −0.1776 | 0.7335 | 0.6710 | 0.049* | |
C15 | −0.13077 (9) | 0.55121 (15) | 0.85901 (17) | 0.0367 (4) | |
H15A | −0.1507 | 0.6012 | 0.9317 | 0.044* | |
H15B | −0.1753 | 0.5168 | 0.7991 | 0.044* | |
C16 | −0.05760 (10) | 0.56874 (15) | 0.65824 (17) | 0.0370 (4) | |
H16A | −0.0300 | 0.4895 | 0.6910 | 0.044* | |
H16B | −0.1030 | 0.5430 | 0.5950 | 0.044* | |
C17 | −0.08440 (9) | 0.63973 (14) | 0.77797 (16) | 0.0310 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0357 (6) | 0.0295 (6) | 0.0647 (8) | −0.0003 (5) | −0.0012 (6) | 0.0038 (6) |
O2 | 0.0452 (7) | 0.0361 (7) | 0.0795 (10) | 0.0024 (5) | −0.0018 (7) | −0.0067 (6) |
C1 | 0.0332 (8) | 0.0296 (8) | 0.0625 (12) | −0.0022 (6) | 0.0010 (8) | 0.0099 (8) |
C2 | 0.0370 (15) | 0.0368 (14) | 0.047 (2) | 0.0024 (11) | 0.0000 (14) | 0.0053 (15) |
C3 | 0.0481 (18) | 0.0458 (16) | 0.084 (3) | 0.0132 (13) | −0.0108 (17) | 0.0029 (18) |
C2' | 0.038 (3) | 0.042 (3) | 0.046 (4) | 0.001 (2) | 0.007 (3) | 0.006 (3) |
C3' | 0.054 (5) | 0.063 (5) | 0.087 (7) | 0.001 (4) | −0.009 (4) | 0.022 (5) |
C4 | 0.0293 (8) | 0.0450 (10) | 0.0838 (15) | −0.0027 (7) | −0.0115 (9) | 0.0023 (10) |
C5 | 0.0395 (10) | 0.0578 (12) | 0.0636 (13) | −0.0034 (8) | 0.0025 (9) | 0.0059 (10) |
C6 | 0.0416 (10) | 0.0551 (11) | 0.0667 (14) | −0.0019 (9) | 0.0028 (9) | −0.0108 (10) |
C7 | 0.0480 (12) | 0.0656 (13) | 0.0859 (17) | −0.0039 (10) | 0.0058 (11) | −0.0294 (12) |
C8 | 0.0493 (12) | 0.0800 (16) | 0.0777 (16) | −0.0129 (11) | 0.0180 (11) | −0.0067 (13) |
C9 | 0.0368 (9) | 0.0496 (11) | 0.0763 (15) | −0.0067 (8) | −0.0007 (9) | −0.0016 (10) |
C10 | 0.0570 (13) | 0.0523 (13) | 0.119 (2) | −0.0110 (10) | 0.0007 (13) | 0.0100 (13) |
C11 | 0.0639 (15) | 0.0552 (13) | 0.112 (2) | −0.0196 (11) | 0.0132 (14) | −0.0071 (13) |
C12 | 0.097 (2) | 0.0659 (17) | 0.177 (4) | −0.0342 (16) | 0.015 (2) | −0.016 (2) |
C13 | 0.0588 (16) | 0.094 (2) | 0.143 (3) | −0.0092 (14) | 0.0058 (17) | −0.006 (2) |
O3 | 0.0624 (9) | 0.0323 (6) | 0.0598 (9) | 0.0120 (6) | 0.0124 (7) | 0.0012 (6) |
O4 | 0.0542 (8) | 0.0286 (6) | 0.0411 (7) | −0.0050 (5) | −0.0013 (6) | 0.0064 (5) |
O5 | 0.0401 (7) | 0.0417 (6) | 0.0372 (7) | −0.0026 (5) | 0.0048 (5) | 0.0080 (5) |
N1 | 0.0359 (7) | 0.0243 (6) | 0.0330 (8) | −0.0003 (5) | 0.0014 (6) | −0.0004 (6) |
C14 | 0.0453 (10) | 0.0324 (8) | 0.0439 (10) | 0.0046 (7) | −0.0021 (8) | 0.0023 (7) |
C15 | 0.0387 (8) | 0.0306 (8) | 0.0406 (10) | −0.0046 (6) | 0.0043 (7) | 0.0025 (7) |
C16 | 0.0453 (9) | 0.0310 (8) | 0.0344 (9) | −0.0065 (7) | 0.0041 (7) | −0.0010 (7) |
C17 | 0.0331 (8) | 0.0258 (7) | 0.0331 (8) | −0.0017 (6) | −0.0006 (6) | 0.0005 (6) |
O1—C1 | 1.252 (2) | C10—H10B | 0.9900 |
O2—C1 | 1.251 (2) | C11—C13 | 1.497 (4) |
C1—C2' | 1.547 (7) | C11—C12 | 1.520 (3) |
C1—C2 | 1.558 (4) | C11—H11 | 1.0000 |
C2—C3 | 1.522 (4) | C12—H12A | 0.9800 |
C2—C4 | 1.546 (4) | C12—H12B | 0.9800 |
C2—H2 | 0.983 (17) | C12—H12C | 0.9800 |
C3—H3A | 0.9800 | C13—H13A | 0.9800 |
C3—H3B | 0.9800 | C13—H13B | 0.9800 |
C3—H3C | 0.9800 | C13—H13C | 0.9800 |
C2'—C3' | 1.518 (11) | O3—C14 | 1.414 (2) |
C2'—C4 | 1.548 (8) | O3—H3 | 0.90 (3) |
C2'—H2' | 0.98 (2) | O4—C15 | 1.422 (2) |
C3'—H3'1 | 0.9800 | O4—H4 | 0.79 (2) |
C3'—H3'2 | 0.9800 | O5—C16 | 1.4174 (19) |
C3'—H3'3 | 0.9800 | O5—H5A | 0.86 (2) |
C4—C5 | 1.369 (3) | N1—C17 | 1.495 (2) |
C4—C7 | 1.383 (3) | N1—H1A | 0.94 (2) |
C5—C6 | 1.377 (3) | N1—H1B | 0.94 (2) |
C5—H5 | 0.9500 | N1—H1C | 0.91 (2) |
C6—C9 | 1.381 (3) | C14—C17 | 1.526 (2) |
C6—H6 | 0.9500 | C14—H14A | 0.9900 |
C7—C8 | 1.387 (3) | C14—H14B | 0.9900 |
C7—H7 | 0.9500 | C15—C17 | 1.524 (2) |
C8—C9 | 1.380 (3) | C15—H15A | 0.9900 |
C8—H8 | 0.9500 | C15—H15B | 0.9900 |
C9—C10 | 1.509 (3) | C16—C17 | 1.526 (2) |
C10—C11 | 1.513 (4) | C16—H16A | 0.9900 |
C10—H10A | 0.9900 | C16—H16B | 0.9900 |
O2—C1—O1 | 123.26 (16) | C11—C10—H10B | 108.6 |
O2—C1—C2' | 109.6 (3) | H10A—C10—H10B | 107.6 |
O1—C1—C2' | 124.5 (3) | C13—C11—C10 | 114.0 (2) |
O2—C1—C2 | 122.54 (17) | C13—C11—C12 | 110.4 (2) |
O1—C1—C2 | 113.51 (18) | C10—C11—C12 | 110.5 (2) |
C3—C2—C4 | 112.7 (3) | C13—C11—H11 | 107.2 |
C3—C2—C1 | 112.0 (3) | C10—C11—H11 | 107.2 |
C4—C2—C1 | 107.6 (2) | C12—C11—H11 | 107.2 |
C3—C2—H2 | 107.2 (18) | C11—C12—H12A | 109.5 |
C4—C2—H2 | 111.5 (17) | C11—C12—H12B | 109.5 |
C1—C2—H2 | 105.7 (18) | H12A—C12—H12B | 109.5 |
C2—C3—H3A | 109.5 | C11—C12—H12C | 109.5 |
C2—C3—H3B | 109.5 | H12A—C12—H12C | 109.5 |
H3A—C3—H3B | 109.5 | H12B—C12—H12C | 109.5 |
C2—C3—H3C | 109.5 | C11—C13—H13A | 109.5 |
H3A—C3—H3C | 109.5 | C11—C13—H13B | 109.5 |
H3B—C3—H3C | 109.5 | H13A—C13—H13B | 109.5 |
C3'—C2'—C1 | 101.9 (6) | C11—C13—H13C | 109.5 |
C3'—C2'—C4 | 103.9 (7) | H13A—C13—H13C | 109.5 |
C1—C2'—C4 | 108.0 (4) | H13B—C13—H13C | 109.5 |
C3'—C2'—H2' | 97 (3) | C14—O3—H3 | 108.7 (12) |
C1—C2'—H2' | 114 (4) | C15—O4—H4 | 109.7 (13) |
C4—C2'—H2' | 127.3 (18) | C16—O5—H5A | 109.7 (11) |
C2'—C3'—H3'1 | 109.5 | C17—N1—H1A | 114.1 (12) |
C2'—C3'—H3'2 | 109.5 | C17—N1—H1B | 110.8 (12) |
H3'1—C3'—H3'2 | 109.5 | H1A—N1—H1B | 105.3 (16) |
C2'—C3'—H3'3 | 109.5 | C17—N1—H1C | 110.3 (13) |
H3'1—C3'—H3'3 | 109.5 | H1A—N1—H1C | 104.9 (17) |
H3'2—C3'—H3'3 | 109.5 | H1B—N1—H1C | 111.3 (17) |
C5—C4—C7 | 117.28 (18) | O3—C14—C17 | 109.37 (14) |
C5—C4—C2 | 114.7 (2) | O3—C14—H14A | 109.8 |
C7—C4—C2 | 128.0 (2) | C17—C14—H14A | 109.8 |
C5—C4—C2' | 141.6 (3) | O3—C14—H14B | 109.8 |
C7—C4—C2' | 100.3 (3) | C17—C14—H14B | 109.8 |
C4—C5—C6 | 121.6 (2) | H14A—C14—H14B | 108.2 |
C4—C5—H5 | 119.2 | O4—C15—C17 | 111.56 (13) |
C6—C5—H5 | 119.2 | O4—C15—H15A | 109.3 |
C5—C6—C9 | 121.9 (2) | C17—C15—H15A | 109.3 |
C5—C6—H6 | 119.1 | O4—C15—H15B | 109.3 |
C9—C6—H6 | 119.1 | C17—C15—H15B | 109.3 |
C4—C7—C8 | 121.1 (2) | H15A—C15—H15B | 108.0 |
C4—C7—H7 | 119.5 | O5—C16—C17 | 112.09 (12) |
C8—C7—H7 | 119.5 | O5—C16—H16A | 109.2 |
C9—C8—C7 | 121.6 (2) | C17—C16—H16A | 109.2 |
C9—C8—H8 | 119.2 | O5—C16—H16B | 109.2 |
C7—C8—H8 | 119.2 | C17—C16—H16B | 109.2 |
C8—C9—C6 | 116.57 (19) | H16A—C16—H16B | 107.9 |
C8—C9—C10 | 122.1 (2) | N1—C17—C15 | 107.22 (13) |
C6—C9—C10 | 121.3 (2) | N1—C17—C14 | 107.80 (12) |
C9—C10—C11 | 114.6 (2) | C15—C17—C14 | 110.87 (13) |
C9—C10—H10A | 108.6 | N1—C17—C16 | 109.01 (13) |
C11—C10—H10A | 108.6 | C15—C17—C16 | 110.98 (12) |
C9—C10—H10B | 108.6 | C14—C17—C16 | 110.83 (14) |
O2—C1—C2—C3 | 14.9 (4) | C2—C4—C7—C8 | 177.6 (2) |
O1—C1—C2—C3 | −174.3 (3) | C2'—C4—C7—C8 | 171.4 (3) |
O2—C1—C2—C4 | 139.3 (2) | C4—C7—C8—C9 | 1.2 (4) |
O1—C1—C2—C4 | −50.0 (3) | C7—C8—C9—C6 | −0.3 (3) |
O2—C1—C2'—C3' | −83.9 (6) | C7—C8—C9—C10 | 179.1 (2) |
O1—C1—C2'—C3' | 114.1 (6) | C5—C6—C9—C8 | −1.4 (3) |
O2—C1—C2'—C4 | 167.0 (4) | C5—C6—C9—C10 | 179.2 (2) |
O1—C1—C2'—C4 | 5.0 (7) | C8—C9—C10—C11 | −90.4 (3) |
C3—C2—C4—C5 | −140.2 (3) | C6—C9—C10—C11 | 89.0 (3) |
C1—C2—C4—C5 | 95.8 (3) | C9—C10—C11—C13 | 65.5 (3) |
C3—C2—C4—C7 | 41.7 (4) | C9—C10—C11—C12 | −169.5 (3) |
C1—C2—C4—C7 | −82.2 (3) | O4—C15—C17—N1 | −55.72 (17) |
C3'—C2'—C4—C5 | −59.3 (7) | O4—C15—C17—C14 | −173.15 (14) |
C1—C2'—C4—C5 | 48.5 (8) | O4—C15—C17—C16 | 63.24 (18) |
C3'—C2'—C4—C7 | 132.5 (5) | O3—C14—C17—N1 | −58.01 (17) |
C1—C2'—C4—C7 | −119.7 (4) | O3—C14—C17—C15 | 59.06 (18) |
C7—C4—C5—C6 | −1.3 (3) | O3—C14—C17—C16 | −177.23 (13) |
C2—C4—C5—C6 | −179.6 (2) | O5—C16—C17—N1 | −56.68 (17) |
C2'—C4—C5—C6 | −168.2 (5) | O5—C16—C17—C15 | −174.56 (13) |
C4—C5—C6—C9 | 2.3 (3) | O5—C16—C17—C14 | 61.80 (18) |
C5—C4—C7—C8 | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.90 (3) | 1.84 (3) | 2.725 (2) | 167 (2) |
O4—H4···O1ii | 0.79 (2) | 1.92 (3) | 2.689 (2) | 163.7 (18) |
O5—H5A···O1 | 0.86 (2) | 2.57 (2) | 3.0825 (19) | 119.5 (17) |
O5—H5A···O2 | 0.86 (2) | 1.88 (2) | 2.730 (2) | 168.1 (18) |
N1—H1A···O1 | 0.94 (2) | 1.85 (2) | 2.763 (2) | 162.9 (18) |
N1—H1B···O4iii | 0.94 (2) | 2.09 (2) | 2.9224 (19) | 146.7 (16) |
N1—H1C···O5iv | 0.91 (2) | 1.97 (2) | 2.806 (2) | 152.1 (18) |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+3/2; (iii) −x, −y+1, −z+2; (iv) x, −y+3/2, z+1/2. |
Acknowledgements
The author is grateful for grants from the Research Project for Young and Middle-aged Faculty of Fujian Province (JA14250) and the Natural Science Foundation of Fujian Province (2015 J01599).
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